# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2021 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_160602YA _audit_block_doi 10.5517/ccdc.csd.cc1mht75 _database_code_depnum_ccdc_archive 'CCDC 1504747' loop_ _citation_id _citation_doi _citation_year 1 10.1021/jacs.6b10278 2016 _audit_update_record ; 2016-12-08 deposited with the CCDC. 2021-02-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 O2' _chemical_formula_sum 'C30 H16 O2' _chemical_formula_weight 408.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1656(12) _cell_length_b 15.1358(14) _cell_length_c 15.7979(16) _cell_angle_alpha 90 _cell_angle_beta 102.4682(19) _cell_angle_gamma 90 _cell_volume 1906.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1574 _cell_measurement_theta_min 31.4 _cell_measurement_theta_max 68.2 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_F_000 848 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.190 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.030 _exptl_absorpt_coefficient_mu 0.696 _shelx_estimated_absorpt_T_min 0.879 _shelx_estimated_absorpt_T_max 0.979 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 12720 _diffrn_reflns_av_unetI/netI 0.0126 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 6.515 _diffrn_reflns_theta_max 68.228 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measured_fraction_theta_full 0.970 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_Laue_measured_fraction_full 0.970 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_point_group_measured_fraction_full 0.970 _reflns_number_total 3386 _reflns_number_gt 3094 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.4445P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3386 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.14947(9) 0.50814(5) 0.09751(5) 0.02301(19) Uani 1 1 d . . . . . O2 O 0.99146(10) 0.66839(5) 0.16172(5) 0.02483(19) Uani 1 1 d . . . . . C3 C 0.51898(13) 0.42501(7) 0.24333(6) 0.0181(2) Uani 1 1 d . . . . . C4 C 0.69467(14) 0.42075(7) 0.25275(6) 0.0192(2) Uani 1 1 d . . . . . H1 H 0.7474 0.4565 0.2170 0.023 Uiso 1 1 calc R U . . . C5 C 0.40936(13) 0.48001(7) 0.18155(6) 0.0180(2) Uani 1 1 d . . . . . C6 C 0.23893(14) 0.46332(7) 0.16796(7) 0.0207(2) Uani 1 1 d . . . . . C7 C 0.26483(15) 0.36073(8) 0.28171(7) 0.0251(3) Uani 1 1 d . . . . . H2 H 0.2172 0.3238 0.3187 0.030 Uiso 1 1 calc R U . . . C8 C 0.55834(14) 0.59920(7) 0.09501(7) 0.0187(2) Uani 1 1 d . . . . . C9 C 0.35417(15) 0.63859(7) -0.04085(7) 0.0242(3) Uani 1 1 d . . . . . H3 H 0.3327 0.6662 -0.0961 0.029 Uiso 1 1 calc R U . . . C10 C 0.67809(15) 0.58154(8) 0.48419(7) 0.0265(3) Uani 1 1 d . . . . . H4 H 0.6519 0.5675 0.5384 0.032 Uiso 1 1 calc R U . . . C11 C 0.26654(14) 0.55547(7) 0.06608(7) 0.0210(2) Uani 1 1 d . . . . . C12 C 0.80218(14) 0.62211(7) 0.23964(7) 0.0194(2) Uani 1 1 d . . . . . C13 C 0.42670(13) 0.54686(7) 0.11741(6) 0.0184(2) Uani 1 1 d . . . . . C14 C 0.52100(15) 0.63716(7) 0.00945(7) 0.0216(2) Uani 1 1 d . . . . . C15 C 0.16151(15) 0.40616(8) 0.21671(7) 0.0251(3) Uani 1 1 d . . . . . H5 H 0.0431 0.3993 0.2052 0.030 Uiso 1 1 calc R U . . . C16 C 0.64921(16) 0.67672(7) -0.02606(7) 0.0246(3) Uani 1 1 d . . . . . H6 H 0.6214 0.6998 -0.0833 0.030 Uiso 1 1 calc R U . . . C17 C 0.54610(15) 0.31426(7) 0.35857(7) 0.0243(3) Uani 1 1 d . . . . . H7 H 0.4964 0.2788 0.3958 0.029 Uiso 1 1 calc R U . . . C18 C 0.44225(14) 0.36759(7) 0.29510(7) 0.0212(2) Uani 1 1 d . . . . . C19 C 1.05317(15) 0.62744(8) 0.39314(8) 0.0289(3) Uani 1 1 d . . . . . H8 H 1.1386 0.6240 0.4445 0.035 Uiso 1 1 calc R U . . . C20 C 0.58564(14) 0.60741(7) 0.33064(7) 0.0207(2) Uani 1 1 d . . . . . H9 H 0.4968 0.6149 0.2813 0.025 Uiso 1 1 calc R U . . . C21 C 0.71976(14) 0.62083(7) 0.14757(7) 0.0193(2) Uani 1 1 d . . . . . C22 C 0.88412(14) 0.60925(7) 0.39750(7) 0.0236(2) Uani 1 1 d . . . . . C23 C 0.83984(14) 0.65519(7) 0.10589(7) 0.0218(2) Uani 1 1 d . . . . . C24 C 0.84126(15) 0.59104(8) 0.47799(7) 0.0264(3) Uani 1 1 d . . . . . H10 H 0.9278 0.5853 0.5286 0.032 Uiso 1 1 calc R U . . . C25 C 0.54903(15) 0.59256(7) 0.41028(7) 0.0242(2) Uani 1 1 d . . . . . H11 H 0.4353 0.5897 0.4154 0.029 Uiso 1 1 calc R U . . . C26 C 0.75308(14) 0.61173(7) 0.32113(7) 0.0201(2) Uani 1 1 d . . . . . C27 C 0.79058(15) 0.36571(7) 0.31283(7) 0.0228(2) Uani 1 1 d . . . . . H12 H 0.9085 0.3633 0.3177 0.027 Uiso 1 1 calc R U . . . C28 C 0.96640(14) 0.64655(7) 0.24229(7) 0.0231(2) Uani 1 1 d . . . . . C29 C 0.71584(15) 0.31289(7) 0.36720(7) 0.0255(3) Uani 1 1 d . . . . . H13 H 0.7834 0.2764 0.4098 0.031 Uiso 1 1 calc R U . . . C30 C 0.81050(15) 0.68247(7) 0.01948(7) 0.0254(3) Uani 1 1 d . . . . . H14 H 0.8981 0.7038 -0.0060 0.031 Uiso 1 1 calc R U . . . C31 C 0.22384(15) 0.60145(7) -0.01213(7) 0.0243(3) Uani 1 1 d . . . . . H15 H 0.1110 0.6066 -0.0435 0.029 Uiso 1 1 calc R U . . . C32 C 1.09519(15) 0.64970(8) 0.31670(8) 0.0285(3) Uani 1 1 d . . . . . H16 H 1.2062 0.6665 0.3142 0.034 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0182(4) 0.0269(4) 0.0225(4) -0.0012(3) 0.0010(3) 0.0003(3) O2 0.0229(4) 0.0241(4) 0.0290(4) -0.0016(3) 0.0091(3) -0.0041(3) C3 0.0214(6) 0.0159(5) 0.0169(5) -0.0037(4) 0.0037(4) -0.0012(4) C4 0.0222(6) 0.0173(5) 0.0185(5) -0.0021(4) 0.0050(4) -0.0010(4) C5 0.0194(6) 0.0174(5) 0.0172(5) -0.0040(4) 0.0040(4) -0.0010(4) C6 0.0200(6) 0.0221(5) 0.0190(5) -0.0039(4) 0.0020(4) 0.0009(4) C7 0.0261(6) 0.0250(6) 0.0256(6) -0.0011(4) 0.0090(5) -0.0064(5) C8 0.0233(6) 0.0145(5) 0.0187(5) -0.0020(4) 0.0051(4) 0.0026(4) C9 0.0355(7) 0.0195(5) 0.0163(5) -0.0016(4) 0.0024(5) 0.0048(4) C10 0.0358(7) 0.0236(6) 0.0206(5) -0.0023(4) 0.0072(5) -0.0011(5) C11 0.0222(6) 0.0195(5) 0.0209(5) -0.0038(4) 0.0039(4) 0.0010(4) C12 0.0192(6) 0.0149(5) 0.0233(5) -0.0018(4) 0.0028(4) -0.0004(4) C13 0.0207(6) 0.0166(5) 0.0173(5) -0.0028(4) 0.0028(4) 0.0023(4) C14 0.0324(7) 0.0143(5) 0.0183(5) -0.0026(4) 0.0060(4) 0.0024(4) C15 0.0192(6) 0.0301(6) 0.0262(6) -0.0047(5) 0.0055(4) -0.0052(4) C16 0.0388(7) 0.0163(5) 0.0204(5) -0.0002(4) 0.0102(5) 0.0032(4) C17 0.0319(7) 0.0182(5) 0.0239(5) 0.0019(4) 0.0083(5) -0.0024(4) C18 0.0261(6) 0.0176(5) 0.0206(5) -0.0033(4) 0.0065(4) -0.0026(4) C19 0.0227(7) 0.0306(6) 0.0295(6) -0.0042(5) -0.0028(5) 0.0004(5) C20 0.0228(6) 0.0178(5) 0.0208(5) -0.0040(4) 0.0028(4) -0.0008(4) C21 0.0225(6) 0.0143(5) 0.0214(5) -0.0008(4) 0.0059(4) 0.0014(4) C22 0.0250(6) 0.0195(5) 0.0241(6) -0.0036(4) 0.0009(5) 0.0008(4) C23 0.0234(6) 0.0167(5) 0.0259(5) -0.0026(4) 0.0066(4) -0.0002(4) C24 0.0314(7) 0.0239(6) 0.0205(5) -0.0030(4) -0.0019(5) 0.0010(5) C25 0.0256(6) 0.0222(6) 0.0255(5) -0.0041(4) 0.0073(5) -0.0016(4) C26 0.0235(6) 0.0144(5) 0.0215(5) -0.0024(4) 0.0029(4) -0.0004(4) C27 0.0222(6) 0.0231(5) 0.0229(5) -0.0008(4) 0.0046(4) 0.0030(4) C28 0.0235(6) 0.0193(5) 0.0270(6) -0.0021(4) 0.0069(5) -0.0009(4) C29 0.0323(7) 0.0209(5) 0.0223(5) 0.0034(4) 0.0040(5) 0.0048(5) C30 0.0344(7) 0.0180(5) 0.0279(6) -0.0005(4) 0.0154(5) -0.0013(4) C31 0.0261(6) 0.0241(6) 0.0197(5) -0.0036(4) -0.0015(4) 0.0057(5) C32 0.0187(6) 0.0296(6) 0.0359(6) -0.0044(5) 0.0032(5) -0.0031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.3705(14) . ? O1 C6 1.3717(13) . ? O2 C23 1.3708(14) . ? O2 C28 1.3726(14) . ? C3 C4 1.4114(16) . ? C3 C18 1.4276(15) . ? C3 C5 1.4385(15) . ? C4 C27 1.3737(15) . ? C5 C6 1.3848(16) . ? C5 C13 1.4603(15) . ? C6 C15 1.3969(16) . ? C7 C15 1.3657(17) . ? C7 C18 1.4220(17) . ? C8 C21 1.4358(16) . ? C8 C14 1.4395(15) . ? C8 C13 1.4396(15) . ? C9 C31 1.3649(17) . ? C9 C14 1.4213(17) . ? C10 C24 1.3646(18) . ? C10 C25 1.4038(16) . ? C11 C13 1.3882(16) . ? C11 C31 1.3952(16) . ? C12 C28 1.3829(16) . ? C12 C26 1.4371(15) . ? C12 C21 1.4650(15) . ? C14 C16 1.4222(16) . ? C16 C30 1.3604(18) . ? C17 C29 1.3633(17) . ? C17 C18 1.4174(16) . ? C19 C32 1.3669(17) . ? C19 C22 1.4238(17) . ? C20 C25 1.3729(15) . ? C20 C26 1.4090(16) . ? C21 C23 1.3944(16) . ? C22 C24 1.4167(16) . ? C22 C26 1.4299(15) . ? C23 C30 1.3964(16) . ? C27 C29 1.4056(16) . ? C28 C32 1.3986(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C6 105.16(8) . . ? C23 O2 C28 105.48(8) . . ? C4 C3 C18 118.26(10) . . ? C4 C3 C5 124.57(10) . . ? C18 C3 C5 117.08(10) . . ? C27 C4 C3 121.03(10) . . ? C6 C5 C3 117.19(10) . . ? C6 C5 C13 105.28(9) . . ? C3 C5 C13 137.09(10) . . ? O1 C6 C5 112.14(9) . . ? O1 C6 C15 121.91(10) . . ? C5 C6 C15 125.93(10) . . ? C15 C7 C18 121.28(10) . . ? C21 C8 C14 115.72(10) . . ? C21 C8 C13 128.63(10) . . ? C14 C8 C13 115.62(10) . . ? C31 C9 C14 122.00(10) . . ? C24 C10 C25 119.81(10) . . ? O1 C11 C13 112.47(9) . . ? O1 C11 C31 121.40(10) . . ? C13 C11 C31 126.01(11) . . ? C28 C12 C26 117.28(10) . . ? C28 C12 C21 105.56(9) . . ? C26 C12 C21 136.94(10) . . ? C11 C13 C8 117.65(9) . . ? C11 C13 C5 104.48(9) . . ? C8 C13 C5 137.84(10) . . ? C9 C14 C16 118.12(10) . . ? C9 C14 C8 120.94(10) . . ? C16 C14 C8 120.91(10) . . ? C7 C15 C6 116.54(10) . . ? C30 C16 C14 121.96(10) . . ? C29 C17 C18 121.29(10) . . ? C17 C18 C7 119.89(10) . . ? C17 C18 C3 118.85(10) . . ? C7 C18 C3 121.22(10) . . ? C32 C19 C22 121.43(11) . . ? C25 C20 C26 120.91(10) . . ? C23 C21 C8 117.60(10) . . ? C23 C21 C12 104.17(9) . . ? C8 C21 C12 138.15(10) . . ? C24 C22 C19 120.73(10) . . ? C24 C22 C26 118.53(11) . . ? C19 C22 C26 120.71(10) . . ? O2 C23 C21 112.33(9) . . ? O2 C23 C30 121.76(10) . . ? C21 C23 C30 125.60(11) . . ? C10 C24 C22 121.28(10) . . ? C20 C25 C10 120.58(11) . . ? C20 C26 C22 118.38(10) . . ? C20 C26 C12 124.44(10) . . ? C22 C26 C12 117.14(10) . . ? C4 C27 C29 120.60(11) . . ? O2 C28 C12 111.96(10) . . ? O2 C28 C32 122.39(10) . . ? C12 C28 C32 125.65(11) . . ? C17 C29 C27 119.77(10) . . ? C16 C30 C23 116.12(10) . . ? C9 C31 C11 115.86(11) . . ? C19 C32 C28 116.58(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 C3 C4 C27 -2.84(15) . . . . ? C5 C3 C4 C27 -179.30(10) . . . . ? C4 C3 C5 C6 166.87(10) . . . . ? C18 C3 C5 C6 -9.62(14) . . . . ? C4 C3 C5 C13 -4.10(18) . . . . ? C18 C3 C5 C13 179.41(11) . . . . ? C11 O1 C6 C5 -0.69(11) . . . . ? C11 O1 C6 C15 -178.94(10) . . . . ? C3 C5 C6 O1 -169.02(8) . . . . ? C13 C5 C6 O1 4.62(11) . . . . ? C3 C5 C6 C15 9.15(16) . . . . ? C13 C5 C6 C15 -177.21(10) . . . . ? C6 O1 C11 C13 -3.91(11) . . . . ? C6 O1 C11 C31 172.35(10) . . . . ? O1 C11 C13 C8 -175.05(9) . . . . ? C31 C11 C13 C8 8.89(16) . . . . ? O1 C11 C13 C5 6.61(11) . . . . ? C31 C11 C13 C5 -169.44(10) . . . . ? C21 C8 C13 C11 162.03(10) . . . . ? C14 C8 C13 C11 -15.81(14) . . . . ? C21 C8 C13 C5 -20.4(2) . . . . ? C14 C8 C13 C5 161.79(11) . . . . ? C6 C5 C13 C11 -6.56(11) . . . . ? C3 C5 C13 C11 165.13(11) . . . . ? C6 C5 C13 C8 175.64(12) . . . . ? C3 C5 C13 C8 -12.7(2) . . . . ? C31 C9 C14 C16 179.36(10) . . . . ? C31 C9 C14 C8 -2.54(16) . . . . ? C21 C8 C14 C9 -164.92(9) . . . . ? C13 C8 C14 C9 13.21(14) . . . . ? C21 C8 C14 C16 13.12(14) . . . . ? C13 C8 C14 C16 -168.75(9) . . . . ? C18 C7 C15 C6 -3.74(16) . . . . ? O1 C6 C15 C7 175.69(10) . . . . ? C5 C6 C15 C7 -2.31(17) . . . . ? C9 C14 C16 C30 176.42(10) . . . . ? C8 C14 C16 C30 -1.67(16) . . . . ? C29 C17 C18 C7 173.51(10) . . . . ? C29 C17 C18 C3 -4.08(16) . . . . ? C15 C7 C18 C17 -174.95(11) . . . . ? C15 C7 C18 C3 2.58(16) . . . . ? C4 C3 C18 C17 5.16(14) . . . . ? C5 C3 C18 C17 -178.11(9) . . . . ? C4 C3 C18 C7 -172.39(9) . . . . ? C5 C3 C18 C7 4.33(14) . . . . ? C14 C8 C21 C23 -16.55(14) . . . . ? C13 C8 C21 C23 165.61(10) . . . . ? C14 C8 C21 C12 159.36(12) . . . . ? C13 C8 C21 C12 -18.5(2) . . . . ? C28 C12 C21 C23 -6.93(11) . . . . ? C26 C12 C21 C23 167.21(12) . . . . ? C28 C12 C21 C8 176.82(12) . . . . ? C26 C12 C21 C8 -9.1(2) . . . . ? C32 C19 C22 C24 -176.49(11) . . . . ? C32 C19 C22 C26 1.50(17) . . . . ? C28 O2 C23 C21 -3.24(11) . . . . ? C28 O2 C23 C30 170.79(10) . . . . ? C8 C21 C23 O2 -176.42(9) . . . . ? C12 C21 C23 O2 6.40(11) . . . . ? C8 C21 C23 C30 9.83(16) . . . . ? C12 C21 C23 C30 -167.35(10) . . . . ? C25 C10 C24 C22 -1.97(17) . . . . ? C19 C22 C24 C10 173.90(11) . . . . ? C26 C22 C24 C10 -4.14(16) . . . . ? C26 C20 C25 C10 0.15(16) . . . . ? C24 C10 C25 C20 4.06(17) . . . . ? C25 C20 C26 C22 -6.23(15) . . . . ? C25 C20 C26 C12 176.40(10) . . . . ? C24 C22 C26 C20 8.12(15) . . . . ? C19 C22 C26 C20 -169.92(10) . . . . ? C24 C22 C26 C12 -174.32(10) . . . . ? C19 C22 C26 C12 7.64(15) . . . . ? C28 C12 C26 C20 164.68(10) . . . . ? C21 C12 C26 C20 -8.96(19) . . . . ? C28 C12 C26 C22 -12.72(14) . . . . ? C21 C12 C26 C22 173.64(11) . . . . ? C3 C4 C27 C29 -0.74(16) . . . . ? C23 O2 C28 C12 -1.62(12) . . . . ? C23 O2 C28 C32 178.50(10) . . . . ? C26 C12 C28 O2 -170.04(9) . . . . ? C21 C12 C28 O2 5.45(12) . . . . ? C26 C12 C28 C32 9.83(16) . . . . ? C21 C12 C28 C32 -174.67(11) . . . . ? C18 C17 C29 C27 0.49(16) . . . . ? C4 C27 C29 C17 1.98(16) . . . . ? C14 C16 C30 C23 -6.02(15) . . . . ? O2 C23 C30 C16 -171.30(9) . . . . ? C21 C23 C30 C16 1.90(16) . . . . ? C14 C9 C31 C11 -5.33(16) . . . . ? O1 C11 C31 C9 -173.63(9) . . . . ? C13 C11 C31 C9 2.10(16) . . . . ? C22 C19 C32 C28 -5.10(17) . . . . ? O2 C28 C32 C19 179.15(10) . . . . ? C12 C28 C32 C19 -0.72(18) . . . . ? _refine_diff_density_max 0.183 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.036 _shelx_res_file ; 160602YA.res created by SHELXL-2014/7 TITL REM Yadorkari-X generated CELL 1.54187 8.1656 15.1358 15.7979 90.0000 102.4682 90.0000 ZERR 4.0 0.0012 0.0014 0.0016 0.0000 0.0019 0.0000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z REM SPGR P21/c monoclinic SFAC C H O UNIT 120 64 8 SIZE 0.19 0.12 0.03 TEMP -180.0 L.S. 10 FMAP 2 PLAN -20 ACTA CONF LIST 4 MERG 2 WGHT 0.050700 0.444500 FVAR 4.75024 O1 3 0.149473 0.508144 0.097507 11.00000 0.01819 0.02686 = 0.02248 -0.00119 0.00103 0.00034 O2 3 0.991456 0.668393 0.161721 11.00000 0.02292 0.02409 = 0.02902 -0.00157 0.00906 -0.00406 C3 1 0.518978 0.425009 0.243325 11.00000 0.02136 0.01588 = 0.01694 -0.00372 0.00366 -0.00123 C4 1 0.694668 0.420749 0.252755 11.00000 0.02217 0.01725 = 0.01854 -0.00209 0.00497 -0.00103 AFIX 43 H1 2 0.747415 0.456505 0.217001 11.00000 -1.20000 AFIX 0 C5 1 0.409363 0.480007 0.181547 11.00000 0.01944 0.01743 = 0.01725 -0.00399 0.00404 -0.00101 C6 1 0.238928 0.463316 0.167959 11.00000 0.02001 0.02209 = 0.01901 -0.00388 0.00200 0.00090 C7 1 0.264829 0.360727 0.281710 11.00000 0.02607 0.02504 = 0.02558 -0.00113 0.00897 -0.00643 AFIX 43 H2 2 0.217248 0.323821 0.318699 11.00000 -1.20000 AFIX 0 C8 1 0.558335 0.599203 0.095012 11.00000 0.02328 0.01450 = 0.01867 -0.00195 0.00508 0.00263 C9 1 0.354173 0.638591 -0.040848 11.00000 0.03551 0.01949 = 0.01626 -0.00156 0.00236 0.00485 AFIX 43 H3 2 0.332730 0.666238 -0.096132 11.00000 -1.20000 AFIX 0 C10 1 0.678088 0.581542 0.484192 11.00000 0.03580 0.02364 = 0.02058 -0.00228 0.00722 -0.00107 AFIX 43 H4 2 0.651905 0.567516 0.538375 11.00000 -1.20000 AFIX 0 C11 1 0.266542 0.555466 0.066081 11.00000 0.02217 0.01948 = 0.02094 -0.00380 0.00394 0.00099 C12 1 0.802184 0.622110 0.239641 11.00000 0.01921 0.01493 = 0.02329 -0.00180 0.00277 -0.00040 C13 1 0.426702 0.546861 0.117413 11.00000 0.02070 0.01659 = 0.01730 -0.00282 0.00277 0.00228 C14 1 0.520999 0.637160 0.009447 11.00000 0.03243 0.01427 = 0.01833 -0.00258 0.00604 0.00241 C15 1 0.161514 0.406162 0.216710 11.00000 0.01916 0.03008 = 0.02623 -0.00468 0.00551 -0.00517 AFIX 43 H5 2 0.043136 0.399257 0.205243 11.00000 -1.20000 AFIX 0 C16 1 0.649207 0.676719 -0.026062 11.00000 0.03879 0.01635 = 0.02044 -0.00016 0.01018 0.00316 AFIX 43 H6 2 0.621382 0.699817 -0.083290 11.00000 -1.20000 AFIX 0 C17 1 0.546099 0.314257 0.358569 11.00000 0.03193 0.01823 = 0.02386 0.00185 0.00834 -0.00235 AFIX 43 H7 2 0.496440 0.278762 0.395825 11.00000 -1.20000 AFIX 0 C18 1 0.442251 0.367592 0.295096 11.00000 0.02608 0.01763 = 0.02055 -0.00329 0.00647 -0.00262 C19 1 1.053172 0.627435 0.393137 11.00000 0.02266 0.03063 = 0.02949 -0.00418 -0.00277 0.00036 AFIX 43 H8 2 1.138612 0.624022 0.444458 11.00000 -1.20000 AFIX 0 C20 1 0.585640 0.607407 0.330645 11.00000 0.02277 0.01776 = 0.02081 -0.00395 0.00280 -0.00083 AFIX 43 H9 2 0.496846 0.614868 0.281279 11.00000 -1.20000 AFIX 0 C21 1 0.719756 0.620831 0.147575 11.00000 0.02253 0.01432 = 0.02142 -0.00075 0.00588 0.00138 C22 1 0.884116 0.609247 0.397504 11.00000 0.02501 0.01950 = 0.02413 -0.00357 0.00087 0.00081 C23 1 0.839843 0.655187 0.105891 11.00000 0.02336 0.01669 = 0.02590 -0.00257 0.00663 -0.00024 C24 1 0.841262 0.591037 0.477986 11.00000 0.03141 0.02387 = 0.02049 -0.00302 -0.00190 0.00099 AFIX 43 H10 2 0.927804 0.585325 0.528613 11.00000 -1.20000 AFIX 0 C25 1 0.549027 0.592560 0.410277 11.00000 0.02563 0.02219 = 0.02547 -0.00408 0.00727 -0.00165 AFIX 43 H11 2 0.435350 0.589717 0.415403 11.00000 -1.20000 AFIX 0 C26 1 0.753084 0.611731 0.321125 11.00000 0.02354 0.01435 = 0.02153 -0.00241 0.00294 -0.00040 C27 1 0.790583 0.365706 0.312827 11.00000 0.02218 0.02308 = 0.02286 -0.00083 0.00456 0.00296 AFIX 43 H12 2 0.908500 0.363312 0.317661 11.00000 -1.20000 AFIX 0 C28 1 0.966403 0.646547 0.242295 11.00000 0.02353 0.01931 = 0.02699 -0.00212 0.00692 -0.00088 C29 1 0.715841 0.312894 0.367205 11.00000 0.03234 0.02092 = 0.02229 0.00343 0.00396 0.00480 AFIX 43 H13 2 0.783373 0.276381 0.409823 11.00000 -1.20000 AFIX 0 C30 1 0.810502 0.682466 0.019483 11.00000 0.03440 0.01799 = 0.02787 -0.00051 0.01539 -0.00132 AFIX 43 H14 2 0.898094 0.703798 -0.006015 11.00000 -1.20000 AFIX 0 C31 1 0.223842 0.601451 -0.012132 11.00000 0.02611 0.02413 = 0.01972 -0.00365 -0.00153 0.00565 AFIX 43 H15 2 0.111044 0.606592 -0.043457 11.00000 -1.20000 AFIX 0 C32 1 1.095192 0.649700 0.316701 11.00000 0.01872 0.02964 = 0.03588 -0.00441 0.00316 -0.00307 AFIX 43 H16 2 1.206187 0.666457 0.314242 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0313 for 3094 Fo > 4sig(Fo) and 0.0341 for all 3386 data REM 289 parameters refined using 0 restraints END WGHT 0.0499 0.4619 REM Highest difference peak 0.183, deepest hole -0.202, 1-sigma level 0.036 Q1 1 0.7367 0.6183 0.1951 11.00000 0.05 0.18 Q2 1 0.8675 0.6591 0.2506 11.00000 0.05 0.18 Q3 1 0.4879 0.5822 0.1215 11.00000 0.05 0.17 Q4 1 0.8202 0.6369 0.3630 11.00000 0.05 0.17 Q5 1 0.4432 0.5228 0.1565 11.00000 0.05 0.17 Q6 1 0.7664 0.6191 0.2771 11.00000 0.05 0.16 Q7 1 0.5595 0.6031 0.0464 11.00000 0.05 0.16 Q8 1 0.3427 0.5808 0.1098 11.00000 0.05 0.16 Q9 1 0.4642 0.4563 0.2096 11.00000 0.05 0.15 Q10 1 0.8246 0.5866 0.3548 11.00000 0.05 0.15 Q11 1 0.3217 0.4979 0.2025 11.00000 0.05 0.15 Q12 1 0.8953 0.6033 0.2404 11.00000 0.05 0.14 Q13 1 0.3583 0.3430 0.2673 11.00000 0.05 0.14 Q14 1 0.8244 0.6593 0.0568 11.00000 0.05 0.14 Q15 1 0.2473 0.5853 0.0298 11.00000 0.05 0.14 Q16 1 0.6563 0.5964 0.1288 11.00000 0.05 0.14 Q17 1 0.7158 0.7050 0.0066 11.00000 0.05 0.14 Q18 1 1.0137 0.6733 0.2815 11.00000 0.05 0.13 Q19 1 0.4686 0.3729 0.2518 11.00000 0.05 0.13 Q20 1 0.5825 0.6727 0.0041 11.00000 0.05 0.13 ; _shelx_res_checksum 37095 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_423yan _audit_block_doi 10.5517/ccdc.csd.cc26qjl2 _database_code_depnum_ccdc_archive 'CCDC 2047444' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1SC00044F 2021 loop_ _audit_author_name _audit_author_address 'Tomoyuki Yanagi' ;Kyoto university Japan ; _audit_update_record ; 2020-12-01 deposited with the CCDC. 2021-02-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H16 O, C0.50 H0.50 Cl1.50' _chemical_formula_sum 'C28.50 H16.50 Cl1.50 O' _chemical_formula_weight 428.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system tetragonal _space_group_IT_number 91 _space_group_name_H-M_alt 'P 41 2 2' _space_group_name_Hall 'P 4w 2c' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z+1/2' '-x, y, -z' '-y, -x, -z+1/4' 'y, x, -z+3/4' 'y, -x, z+3/4' '-y, x, z+1/4' _cell_length_a 9.0201(9) _cell_length_b 9.0201(9) _cell_length_c 49.382(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4017.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3290 _cell_measurement_theta_min 30.7 _cell_measurement_theta_max 72.9 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_F_000 1768 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.270 _exptl_crystal_size_min 0.060 _exptl_absorpt_coefficient_mu 2.437 _shelx_estimated_absorpt_T_min 0.528 _shelx_estimated_absorpt_T_max 0.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.845 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 53658 _diffrn_reflns_av_unetI/netI 0.0181 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -58 _diffrn_reflns_limit_l_max 58 _diffrn_reflns_theta_min 3.580 _diffrn_reflns_theta_max 65.995 _diffrn_reflns_theta_full 65.995 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 3507 _reflns_number_gt 3284 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.614 _reflns_Friedel_fraction_max 0.999 _reflns_Friedel_fraction_full 0.999 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1412P)^2^+7.1101P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.478(5) _chemical_absolute_configuration unk _refine_ls_number_reflns 3507 _refine_ls_number_parameters 299 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.2449 _refine_ls_wR_factor_gt 0.2422 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3653(7) 0.4236(6) 0.64168(9) 0.0670(15) Uani 1 1 d . . . . . C12 C 0.7986(7) 0.2765(7) 0.74398(12) 0.0441(14) Uani 1 1 d . . . . . C13 C 0.5605(7) 0.1758(7) 0.73131(12) 0.0433(14) Uani 1 1 d . . . . . C14 C 0.1853(11) 0.0000 0.7500 0.049(2) Uani 1 2 d S T P . . C15 C 0.3452(10) 0.0000 0.7500 0.0425(19) Uani 1 2 d S T P . . C17 C 0.5742(7) 0.2509(7) 0.70674(11) 0.0446(14) Uani 1 1 d . . . . . C18 C 0.7611(7) 0.1817(7) 0.79740(12) 0.0468(15) Uani 1 1 d . . . . . H1 H 0.7458 0.1520 0.8156 0.056 Uiso 1 1 calc R U . . . C19 C 0.6710(6) 0.1966(7) 0.75138(12) 0.0411(13) Uani 1 1 d . . . . . C20 C 0.4141(7) 0.1019(8) 0.73162(12) 0.0483(16) Uani 1 1 d . . . . . C21 C 0.8140(8) 0.3372(8) 0.71743(13) 0.0501(15) Uani 1 1 d . . . . . H2 H 0.9040 0.3844 0.7124 0.060 Uiso 1 1 calc R U . . . C22 C 0.3472(8) 0.4902(8) 0.66641(14) 0.0531(16) Uani 1 1 d . . . . . C23 C 0.6544(7) 0.1538(7) 0.77875(12) 0.0455(15) Uani 1 1 d . . . . . H3 H 0.5664 0.1042 0.7842 0.055 Uiso 1 1 calc R U . . . C24 C 0.7029(8) 0.3283(8) 0.69964(13) 0.0499(16) Uani 1 1 d . . . . . H4 H 0.7112 0.3739 0.6824 0.060 Uiso 1 1 calc R U . . . C25 C 0.3309(8) 0.1581(8) 0.71011(12) 0.0505(16) Uani 1 1 d . . . . . C26 C 0.1820(8) 0.1368(8) 0.70755(14) 0.0550(17) Uani 1 1 d . . . . . H5 H 0.1303 0.1704 0.6920 0.066 Uiso 1 1 calc R U . . . C27 C 0.4057(8) 0.2786(8) 0.64028(13) 0.0531(17) Uani 1 1 d . . . . . C28 C 0.4352(8) 0.1913(8) 0.66299(12) 0.0510(16) Uani 1 1 d . . . . . C29 C 0.4259(8) 0.2553(8) 0.69155(12) 0.0501(16) Uani 1 1 d . . . . . C30 C 0.1091(8) 0.0656(8) 0.72802(14) 0.0547(17) Uani 1 1 d . . . . . H6 H 0.0040 0.0601 0.7275 0.066 Uiso 1 1 calc R U . . . C31 C 0.8934(8) 0.2535(8) 0.79036(13) 0.0520(16) Uani 1 1 d . . . . . H7 H 0.9687 0.2695 0.8035 0.062 Uiso 1 1 calc R U . . . C32 C 0.9120(7) 0.3004(8) 0.76402(13) 0.0488(15) Uani 1 1 d . . . . . H8 H 1.0012 0.3492 0.7590 0.059 Uiso 1 1 calc R U . . . C33 C 0.3711(8) 0.4139(8) 0.69052(12) 0.0514(16) Uani 1 1 d . . . . . C34 C 0.3022(9) 0.6362(9) 0.66632(15) 0.0607(18) Uani 1 1 d . . . . . H9 H 0.2863 0.6849 0.6495 0.073 Uiso 1 1 calc R U . . . C35 C 0.2800(8) 0.7119(9) 0.68975(16) 0.0605(19) Uani 1 1 d . . . . . H10 H 0.2496 0.8128 0.6894 0.073 Uiso 1 1 calc R U . . . C36 C 0.4609(10) 0.0750(11) 0.61083(15) 0.072(2) Uani 1 1 d . . . . . H11 H 0.4713 0.0357 0.5931 0.087 Uiso 1 1 calc R U . . . C37 C 0.4194(9) 0.2208(10) 0.61426(13) 0.063(2) Uani 1 1 d . . . . . H12 H 0.4003 0.2816 0.5989 0.076 Uiso 1 1 calc R U . . . C38 C 0.3452(11) 0.4941(10) 0.71440(15) 0.075(3) Uani 1 1 d . . . . . H13 H 0.3578 0.4458 0.7313 0.090 Uiso 1 1 calc R U . . . C39 C 0.4745(10) 0.0440(9) 0.65827(14) 0.066(2) Uani 1 1 d . . . . . H14 H 0.4931 -0.0186 0.6734 0.079 Uiso 1 1 calc R U . . . C40 C 0.3022(11) 0.6398(10) 0.71407(17) 0.074(2) Uani 1 1 d . . . . . H15 H 0.2877 0.6914 0.7306 0.089 Uiso 1 1 calc R U . . . C41 C 0.4874(11) -0.0138(10) 0.63281(15) 0.072(2) Uani 1 1 d . . . . . H16 H 0.5144 -0.1147 0.6304 0.086 Uiso 1 1 calc R U . . . C42 C 0.9274(19) 0.009(3) 0.6239(3) 0.107(6) Uani 0.5 1 d D U P A -1 H17 H 0.8739 -0.0881 0.6239 0.129 Uiso 0.5 1 calc R U P A -1 Cl1 Cl 0.8774(7) 0.1171(6) 0.59609(8) 0.0586(11) Uani 0.5 1 d D U P A -1 Cl2 Cl 0.901(2) 0.102(2) 0.6530(3) 0.222(7) Uani 0.5 1 d D U P A -1 Cl3 Cl 1.1163(7) -0.0156(8) 0.6243(2) 0.133(2) Uani 0.5 1 d D U P A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.088(4) 0.067(3) 0.046(3) -0.005(2) -0.010(2) 0.023(3) C12 0.047(3) 0.041(3) 0.044(3) -0.006(3) 0.001(3) -0.001(3) C13 0.047(3) 0.047(4) 0.036(3) -0.008(3) 0.004(2) 0.004(3) C14 0.048(5) 0.047(5) 0.051(5) -0.013(4) 0.000 0.000 C15 0.043(5) 0.041(4) 0.043(4) -0.016(4) 0.000 0.000 C17 0.048(3) 0.047(3) 0.038(3) -0.008(3) -0.004(3) 0.008(3) C18 0.053(4) 0.048(3) 0.039(3) -0.011(3) -0.003(3) 0.005(3) C19 0.040(3) 0.043(3) 0.041(3) -0.009(2) 0.002(2) 0.005(2) C20 0.048(4) 0.060(4) 0.037(3) -0.008(3) -0.005(3) 0.002(3) C21 0.053(4) 0.049(4) 0.049(3) -0.007(3) 0.007(3) -0.001(3) C22 0.051(4) 0.060(4) 0.049(3) -0.009(3) -0.006(3) 0.011(3) C23 0.046(4) 0.050(4) 0.041(3) -0.005(3) 0.001(3) 0.004(3) C24 0.053(4) 0.052(4) 0.044(3) 0.001(3) 0.005(3) 0.011(3) C25 0.052(4) 0.056(4) 0.043(3) -0.008(3) -0.006(3) 0.007(3) C26 0.063(4) 0.053(4) 0.049(3) -0.018(3) -0.011(3) 0.010(3) C27 0.058(4) 0.054(4) 0.048(3) -0.011(3) -0.011(3) 0.006(3) C28 0.056(4) 0.057(4) 0.040(3) -0.007(3) -0.006(3) 0.008(3) C29 0.052(4) 0.055(4) 0.043(3) -0.005(3) -0.013(3) 0.011(3) C30 0.044(4) 0.059(4) 0.061(4) -0.017(3) -0.003(3) 0.008(3) C31 0.049(4) 0.058(4) 0.049(3) -0.013(3) -0.006(3) 0.000(3) C32 0.039(3) 0.054(4) 0.054(4) -0.009(3) -0.003(3) 0.001(3) C33 0.051(4) 0.061(4) 0.042(3) -0.010(3) -0.010(3) 0.010(3) C34 0.062(4) 0.066(5) 0.055(4) -0.005(3) -0.008(3) 0.014(4) C35 0.055(4) 0.054(4) 0.072(4) -0.007(3) -0.013(4) 0.002(3) C36 0.079(6) 0.087(6) 0.051(4) -0.026(4) -0.011(4) 0.012(5) C37 0.075(5) 0.074(5) 0.040(3) -0.006(3) -0.008(3) 0.010(4) C38 0.107(7) 0.071(5) 0.046(4) -0.007(4) -0.019(4) 0.032(5) C39 0.091(6) 0.063(5) 0.043(4) -0.003(3) -0.008(4) 0.020(4) C40 0.090(6) 0.067(5) 0.066(4) -0.022(4) -0.013(4) 0.024(5) C41 0.089(6) 0.065(5) 0.060(4) -0.023(4) -0.010(4) 0.020(5) C42 0.114(10) 0.120(10) 0.088(8) -0.014(9) -0.011(9) -0.002(9) Cl1 0.090(3) 0.059(2) 0.0264(13) -0.0082(15) -0.0097(17) 0.012(2) Cl2 0.243(14) 0.269(15) 0.155(10) -0.016(10) 0.017(10) -0.040(12) Cl3 0.093(4) 0.112(4) 0.193(6) -0.019(5) 0.002(5) 0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C27 1.360(9) . ? O1 C22 1.371(8) . ? C12 C19 1.406(9) . ? C12 C21 1.428(9) . ? C12 C32 1.440(9) . ? C13 C17 1.395(9) . ? C13 C19 1.418(9) . ? C13 C20 1.479(9) . ? C14 C30 1.415(9) 3_556 ? C14 C30 1.415(9) . ? C14 C15 1.442(13) . ? C15 C20 1.433(8) . ? C15 C20 1.433(8) 3_556 ? C17 C24 1.400(10) . ? C17 C29 1.534(9) . ? C18 C23 1.355(9) . ? C18 C31 1.402(10) . ? C18 H1 0.9500 . ? C19 C23 1.414(8) . ? C20 C25 1.396(9) . ? C21 C24 1.335(10) . ? C21 H2 0.9500 . ? C22 C34 1.378(11) . ? C22 C33 1.391(10) . ? C23 H3 0.9500 . ? C24 H4 0.9500 . ? C25 C26 1.363(10) . ? C25 C29 1.530(10) . ? C26 C30 1.366(11) . ? C26 H5 0.9500 . ? C27 C37 1.392(9) . ? C27 C28 1.396(10) . ? C28 C39 1.394(11) . ? C28 C29 1.526(8) . ? C29 C33 1.515(10) . ? C30 H6 0.9500 . ? C31 C32 1.378(9) . ? C31 H7 0.9500 . ? C32 H8 0.9500 . ? C33 C38 1.403(10) . ? C34 C35 1.359(10) . ? C34 H9 0.9500 . ? C35 C40 1.380(12) . ? C35 H10 0.9500 . ? C36 C41 1.370(12) . ? C36 C37 1.378(12) . ? C36 H11 0.9500 . ? C37 H12 0.9500 . ? C38 C40 1.370(11) . ? C38 H13 0.9500 . ? C39 C41 1.366(10) . ? C39 H14 0.9500 . ? C40 H15 0.9500 . ? C41 H16 0.9500 . ? C42 Cl2 1.678(18) . ? C42 Cl3 1.719(16) . ? C42 Cl1 1.743(17) . ? C42 H17 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C27 O1 C22 119.9(6) . . ? C19 C12 C21 121.0(6) . . ? C19 C12 C32 118.7(6) . . ? C21 C12 C32 120.3(6) . . ? C17 C13 C19 118.8(6) . . ? C17 C13 C20 107.9(5) . . ? C19 C13 C20 132.8(6) . . ? C30 C14 C30 121.8(9) 3_556 . ? C30 C14 C15 119.1(5) 3_556 . ? C30 C14 C15 119.1(5) . . ? C20 C15 C20 128.6(9) . 3_556 ? C20 C15 C14 115.7(4) . . ? C20 C15 C14 115.7(4) 3_556 . ? C13 C17 C24 122.2(6) . . ? C13 C17 C29 111.1(6) . . ? C24 C17 C29 126.0(6) . . ? C23 C18 C31 121.5(6) . . ? C23 C18 H1 119.3 . . ? C31 C18 H1 119.3 . . ? C12 C19 C23 118.3(6) . . ? C12 C19 C13 117.5(6) . . ? C23 C19 C13 123.9(6) . . ? C25 C20 C15 118.8(6) . . ? C25 C20 C13 107.9(6) . . ? C15 C20 C13 133.1(6) . . ? C24 C21 C12 120.5(6) . . ? C24 C21 H2 119.7 . . ? C12 C21 H2 119.7 . . ? O1 C22 C34 116.8(6) . . ? O1 C22 C33 121.8(6) . . ? C34 C22 C33 121.4(6) . . ? C18 C23 C19 121.6(6) . . ? C18 C23 H3 119.2 . . ? C19 C23 H3 119.2 . . ? C21 C24 C17 119.2(6) . . ? C21 C24 H4 120.4 . . ? C17 C24 H4 120.4 . . ? C26 C25 C20 123.3(7) . . ? C26 C25 C29 125.3(6) . . ? C20 C25 C29 111.3(6) . . ? C25 C26 C30 118.2(7) . . ? C25 C26 H5 120.9 . . ? C30 C26 H5 120.9 . . ? O1 C27 C37 115.5(7) . . ? O1 C27 C28 123.6(6) . . ? C37 C27 C28 120.9(7) . . ? C39 C28 C27 116.9(6) . . ? C39 C28 C29 121.9(6) . . ? C27 C28 C29 121.2(6) . . ? C33 C29 C28 110.1(5) . . ? C33 C29 C25 112.2(6) . . ? C28 C29 C25 111.6(6) . . ? C33 C29 C17 109.0(6) . . ? C28 C29 C17 113.2(6) . . ? C25 C29 C17 100.4(5) . . ? C26 C30 C14 122.0(7) . . ? C26 C30 H6 119.0 . . ? C14 C30 H6 119.0 . . ? C32 C31 C18 118.7(6) . . ? C32 C31 H7 120.7 . . ? C18 C31 H7 120.7 . . ? C31 C32 C12 121.1(6) . . ? C31 C32 H8 119.4 . . ? C12 C32 H8 119.4 . . ? C22 C33 C38 116.0(7) . . ? C22 C33 C29 123.1(6) . . ? C38 C33 C29 120.9(6) . . ? C35 C34 C22 121.4(7) . . ? C35 C34 H9 119.3 . . ? C22 C34 H9 119.3 . . ? C34 C35 C40 118.9(7) . . ? C34 C35 H10 120.6 . . ? C40 C35 H10 120.6 . . ? C41 C36 C37 120.5(7) . . ? C41 C36 H11 119.7 . . ? C37 C36 H11 119.7 . . ? C36 C37 C27 119.7(7) . . ? C36 C37 H12 120.2 . . ? C27 C37 H12 120.2 . . ? C40 C38 C33 122.1(7) . . ? C40 C38 H13 119.0 . . ? C33 C38 H13 119.0 . . ? C41 C39 C28 122.6(7) . . ? C41 C39 H14 118.7 . . ? C28 C39 H14 118.7 . . ? C38 C40 C35 120.2(7) . . ? C38 C40 H15 119.9 . . ? C35 C40 H15 119.9 . . ? C39 C41 C36 119.4(8) . . ? C39 C41 H16 120.3 . . ? C36 C41 H16 120.3 . . ? Cl2 C42 Cl3 101.3(12) . . ? Cl2 C42 Cl1 111.0(13) . . ? Cl3 C42 Cl1 109.8(13) . . ? Cl2 C42 H17 111.5 . . ? Cl3 C42 H17 111.5 . . ? Cl1 C42 H17 111.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C30 C14 C15 C20 -163.2(4) 3_556 . . . ? C30 C14 C15 C20 16.8(4) . . . . ? C30 C14 C15 C20 16.7(4) 3_556 . . 3_556 ? C30 C14 C15 C20 -163.3(4) . . . 3_556 ? C19 C13 C17 C24 9.6(9) . . . . ? C20 C13 C17 C24 -177.7(6) . . . . ? C19 C13 C17 C29 -162.0(6) . . . . ? C20 C13 C17 C29 10.7(7) . . . . ? C21 C12 C19 C23 -172.9(6) . . . . ? C32 C12 C19 C23 5.1(9) . . . . ? C21 C12 C19 C13 1.5(9) . . . . ? C32 C12 C19 C13 179.5(5) . . . . ? C17 C13 C19 C12 -8.3(8) . . . . ? C20 C13 C19 C12 -178.9(6) . . . . ? C17 C13 C19 C23 165.8(6) . . . . ? C20 C13 C19 C23 -4.8(11) . . . . ? C20 C15 C20 C25 160.9(6) 3_556 . . . ? C14 C15 C20 C25 -19.1(6) . . . . ? C20 C15 C20 C13 -25.0(6) 3_556 . . . ? C14 C15 C20 C13 155.0(6) . . . . ? C17 C13 C20 C25 -12.1(7) . . . . ? C19 C13 C20 C25 159.2(7) . . . . ? C17 C13 C20 C15 173.3(6) . . . . ? C19 C13 C20 C15 -15.3(12) . . . . ? C19 C12 C21 C24 4.7(9) . . . . ? C32 C12 C21 C24 -173.3(6) . . . . ? C27 O1 C22 C34 -178.3(7) . . . . ? C27 O1 C22 C33 0.9(11) . . . . ? C31 C18 C23 C19 -0.5(10) . . . . ? C12 C19 C23 C18 -3.2(9) . . . . ? C13 C19 C23 C18 -177.2(6) . . . . ? C12 C21 C24 C17 -3.8(10) . . . . ? C13 C17 C24 C21 -3.4(10) . . . . ? C29 C17 C24 C21 166.9(6) . . . . ? C15 C20 C25 C26 8.9(10) . . . . ? C13 C20 C25 C26 -166.5(6) . . . . ? C15 C20 C25 C29 -175.7(5) . . . . ? C13 C20 C25 C29 8.9(7) . . . . ? C20 C25 C26 C30 4.7(10) . . . . ? C29 C25 C26 C30 -170.1(6) . . . . ? C22 O1 C27 C37 179.2(7) . . . . ? C22 O1 C27 C28 -2.0(11) . . . . ? O1 C27 C28 C39 179.6(8) . . . . ? C37 C27 C28 C39 -1.7(12) . . . . ? O1 C27 C28 C29 -0.9(12) . . . . ? C37 C27 C28 C29 177.8(7) . . . . ? C39 C28 C29 C33 -176.3(7) . . . . ? C27 C28 C29 C33 4.3(10) . . . . ? C39 C28 C29 C25 -50.9(10) . . . . ? C27 C28 C29 C25 129.6(7) . . . . ? C39 C28 C29 C17 61.4(10) . . . . ? C27 C28 C29 C17 -118.0(7) . . . . ? C26 C25 C29 C33 57.2(8) . . . . ? C20 C25 C29 C33 -118.1(6) . . . . ? C26 C25 C29 C28 -67.0(9) . . . . ? C20 C25 C29 C28 117.7(6) . . . . ? C26 C25 C29 C17 172.8(6) . . . . ? C20 C25 C29 C17 -2.5(7) . . . . ? C13 C17 C29 C33 112.8(6) . . . . ? C24 C17 C29 C33 -58.4(8) . . . . ? C13 C17 C29 C28 -124.3(6) . . . . ? C24 C17 C29 C28 64.5(9) . . . . ? C13 C17 C29 C25 -5.3(7) . . . . ? C24 C17 C29 C25 -176.5(6) . . . . ? C25 C26 C30 C14 -7.1(10) . . . . ? C30 C14 C30 C26 176.1(7) 3_556 . . . ? C15 C14 C30 C26 -3.9(7) . . . . ? C23 C18 C31 C32 2.1(10) . . . . ? C18 C31 C32 C12 -0.1(10) . . . . ? C19 C12 C32 C31 -3.6(9) . . . . ? C21 C12 C32 C31 174.4(6) . . . . ? O1 C22 C33 C38 -178.5(7) . . . . ? C34 C22 C33 C38 0.6(12) . . . . ? O1 C22 C33 C29 3.1(12) . . . . ? C34 C22 C33 C29 -177.7(7) . . . . ? C28 C29 C33 C22 -5.4(10) . . . . ? C25 C29 C33 C22 -130.3(7) . . . . ? C17 C29 C33 C22 119.4(7) . . . . ? C28 C29 C33 C38 176.3(8) . . . . ? C25 C29 C33 C38 51.4(9) . . . . ? C17 C29 C33 C38 -58.9(9) . . . . ? O1 C22 C34 C35 179.5(7) . . . . ? C33 C22 C34 C35 0.3(12) . . . . ? C22 C34 C35 C40 -0.5(12) . . . . ? C41 C36 C37 C27 0.6(14) . . . . ? O1 C27 C37 C36 179.6(8) . . . . ? C28 C27 C37 C36 0.8(13) . . . . ? C22 C33 C38 C40 -1.5(14) . . . . ? C29 C33 C38 C40 176.9(9) . . . . ? C27 C28 C39 C41 1.4(13) . . . . ? C29 C28 C39 C41 -178.1(8) . . . . ? C33 C38 C40 C35 1.4(16) . . . . ? C34 C35 C40 C38 -0.4(14) . . . . ? C28 C39 C41 C36 0.0(15) . . . . ? C37 C36 C41 C39 -1.0(15) . . . . ? _refine_diff_density_max 0.932 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.084 _shelx_res_file ; 423yan.res created by SHELXL-2014/7 TITL 423yan_a.res in P4(1)22 REM Yadorkari-X generated CELL 1.54187 9.0201 9.0201 49.3820 90.0000 90.0000 90.0000 ZERR 8.0 0.0009 0.0009 0.0070 0.0000 0.0000 0.0000 LATT -1 SYMM -X, -Y, 1/2+Z SYMM +X, -Y, 1/2-Z SYMM -X, +Y, -Z SYMM -Y, -X, 1/4-Z SYMM +Y, +X, 3/4-Z SYMM +Y, -X, 3/4+Z SYMM -Y, +X, 1/4+Z REM SPGR P4122 tetragonal SFAC C H O Cl UNIT 228 132 8 12 SIZE 0.30 0.27 0.06 TEMP -180.0 L.S. 20 FMAP 2 PLAN -20 ACTA CONF HTAB LIST 4 BOND $H OMIT -10.000000 132.000000 OMIT 0 2 42 ISOR 0.01 C42 Cl1 Cl2 Cl3 SIMU 0.01 C42 Cl1 Cl2 Cl3 SADI 0.02 C42 Cl1 C42 Cl2 C42 Cl3 WGHT 0.141200 7.110100 FVAR 1.99176 O1 3 0.365278 0.423644 0.641680 11.00000 0.08758 0.06692 = 0.04642 -0.00459 -0.00978 0.02328 C12 1 0.798552 0.276522 0.743983 11.00000 0.04723 0.04093 = 0.04418 -0.00639 0.00106 -0.00087 C13 1 0.560468 0.175825 0.731310 11.00000 0.04666 0.04733 = 0.03589 -0.00767 0.00419 0.00416 C14 1 0.185347 0.000000 0.750000 10.50000 0.04791 0.04711 = 0.05103 -0.01260 0.00000 0.00000 C15 1 0.345212 0.000000 0.750000 10.50000 0.04344 0.04062 = 0.04349 -0.01564 0.00000 0.00000 C17 1 0.574187 0.250867 0.706736 11.00000 0.04806 0.04748 = 0.03834 -0.00847 -0.00391 0.00815 C18 1 0.761074 0.181739 0.797400 11.00000 0.05333 0.04759 = 0.03940 -0.01062 -0.00335 0.00507 AFIX 43 H1 2 0.745822 0.152031 0.815645 11.00000 -1.20000 AFIX 0 C19 1 0.670953 0.196589 0.751380 11.00000 0.03992 0.04276 = 0.04055 -0.00878 0.00232 0.00524 C20 1 0.414090 0.101879 0.731624 11.00000 0.04772 0.06034 = 0.03682 -0.00821 -0.00487 0.00159 C21 1 0.814002 0.337215 0.717435 11.00000 0.05260 0.04871 = 0.04894 -0.00671 0.00709 -0.00075 AFIX 43 H2 2 0.904040 0.384357 0.712389 11.00000 -1.20000 AFIX 0 C22 1 0.347190 0.490151 0.666414 11.00000 0.05058 0.06000 = 0.04857 -0.00894 -0.00608 0.01108 C23 1 0.654390 0.153783 0.778755 11.00000 0.04575 0.04979 = 0.04082 -0.00535 0.00127 0.00390 AFIX 43 H3 2 0.566383 0.104241 0.784212 11.00000 -1.20000 AFIX 0 C24 1 0.702947 0.328258 0.699644 11.00000 0.05306 0.05245 = 0.04405 0.00092 0.00486 0.01066 AFIX 43 H4 2 0.711212 0.373881 0.682370 11.00000 -1.20000 AFIX 0 C25 1 0.330939 0.158100 0.710106 11.00000 0.05204 0.05613 = 0.04326 -0.00830 -0.00632 0.00716 C26 1 0.181982 0.136762 0.707551 11.00000 0.06318 0.05281 = 0.04906 -0.01843 -0.01104 0.01012 AFIX 43 H5 2 0.130281 0.170444 0.691961 11.00000 -1.20000 AFIX 0 C27 1 0.405716 0.278628 0.640280 11.00000 0.05751 0.05392 = 0.04798 -0.01122 -0.01142 0.00639 C28 1 0.435245 0.191257 0.662987 11.00000 0.05618 0.05688 = 0.04001 -0.00659 -0.00636 0.00826 C29 1 0.425929 0.255266 0.691548 11.00000 0.05236 0.05548 = 0.04257 -0.00452 -0.01324 0.01138 C30 1 0.109106 0.065638 0.728018 11.00000 0.04357 0.05921 = 0.06136 -0.01665 -0.00280 0.00783 AFIX 43 H6 2 0.003975 0.060063 0.727478 11.00000 -1.20000 AFIX 0 C31 1 0.893403 0.253511 0.790356 11.00000 0.04942 0.05768 = 0.04904 -0.01284 -0.00561 0.00040 AFIX 43 H7 2 0.968744 0.269521 0.803477 11.00000 -1.20000 AFIX 0 C32 1 0.911991 0.300359 0.764024 11.00000 0.03868 0.05387 = 0.05372 -0.00880 -0.00277 0.00112 AFIX 43 H8 2 1.001157 0.349213 0.759004 11.00000 -1.20000 AFIX 0 C33 1 0.371119 0.413924 0.690516 11.00000 0.05092 0.06098 = 0.04219 -0.00996 -0.00981 0.00982 C34 1 0.302174 0.636176 0.666322 11.00000 0.06157 0.06552 = 0.05510 -0.00512 -0.00780 0.01371 AFIX 43 H9 2 0.286347 0.684902 0.649513 11.00000 -1.20000 AFIX 0 C35 1 0.279951 0.711918 0.689751 11.00000 0.05501 0.05436 = 0.07212 -0.00660 -0.01325 0.00155 AFIX 43 H10 2 0.249601 0.812753 0.689405 11.00000 -1.20000 AFIX 0 C36 1 0.460933 0.074960 0.610825 11.00000 0.07890 0.08669 = 0.05141 -0.02595 -0.01063 0.01153 AFIX 43 H11 2 0.471292 0.035688 0.593076 11.00000 -1.20000 AFIX 0 C37 1 0.419436 0.220809 0.614259 11.00000 0.07472 0.07450 = 0.03994 -0.00629 -0.00774 0.00989 AFIX 43 H12 2 0.400286 0.281599 0.598944 11.00000 -1.20000 AFIX 0 C38 1 0.345166 0.494116 0.714403 11.00000 0.10731 0.07128 = 0.04581 -0.00671 -0.01929 0.03242 AFIX 43 H13 2 0.357764 0.445848 0.731346 11.00000 -1.20000 AFIX 0 C39 1 0.474533 0.044007 0.658266 11.00000 0.09142 0.06302 = 0.04324 -0.00308 -0.00760 0.02005 AFIX 43 H14 2 0.493126 -0.018613 0.673356 11.00000 -1.20000 AFIX 0 C40 1 0.302227 0.639845 0.714065 11.00000 0.09048 0.06659 = 0.06628 -0.02198 -0.01303 0.02415 AFIX 43 H15 2 0.287744 0.691434 0.730627 11.00000 -1.20000 AFIX 0 C41 1 0.487351 -0.013796 0.632808 11.00000 0.08938 0.06513 = 0.06033 -0.02302 -0.00985 0.02028 AFIX 43 H16 2 0.514363 -0.114714 0.630368 11.00000 -1.20000 PART -1 AFIX 0 C42 1 0.927397 0.009004 0.623888 10.50000 0.11416 0.12011 = 0.08755 -0.01362 -0.01138 -0.00193 AFIX 13 H17 2 0.873882 -0.088088 0.623911 10.50000 -1.20000 AFIX 0 CL1 4 0.877372 0.117082 0.596092 10.50000 0.09028 0.05919 = 0.02638 -0.00821 -0.00970 0.01213 CL2 4 0.900751 0.101598 0.652966 10.50000 0.24274 0.26875 = 0.15500 -0.01626 0.01712 -0.04009 CL3 4 1.116319 -0.015559 0.624301 10.50000 0.09292 0.11211 = 0.19320 -0.01949 0.00247 0.01634 PART 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 423yan_a.res in P4(1)22 REM R1 = 0.0853 for 3284 Fo > 4sig(Fo) and 0.0888 for all 3507 data REM 299 parameters refined using 45 restraints END WGHT 0.1545 4.6184 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.932, deepest hole -0.481, 1-sigma level 0.084 Q1 1 0.7540 0.2460 0.6250 10.50000 0.05 0.93 Q2 1 0.5900 -0.0020 0.5935 11.00000 0.05 0.71 Q3 1 0.0370 -0.0159 0.6537 11.00000 0.05 0.60 Q4 1 0.6181 -0.0057 0.6521 11.00000 0.05 0.58 Q5 1 0.1330 -0.0965 0.6506 11.00000 0.05 0.51 Q6 1 0.1359 0.1063 0.6241 11.00000 0.05 0.39 Q7 1 0.3026 0.3041 0.6400 11.00000 0.05 0.38 Q8 1 0.2214 0.3736 0.6823 11.00000 0.05 0.36 Q9 1 0.6722 0.2643 0.7856 11.00000 0.05 0.34 Q10 1 0.8928 0.1965 0.7483 11.00000 0.05 0.32 Q11 1 0.1336 0.2296 0.6871 11.00000 0.05 0.31 Q12 1 0.2172 0.4686 0.7025 11.00000 0.05 0.30 Q13 1 0.2712 0.3965 0.6588 11.00000 0.05 0.30 Q14 1 0.9974 0.2399 0.7020 11.00000 0.05 0.29 Q15 1 0.2294 0.1891 0.6378 11.00000 0.05 0.29 Q16 1 0.1305 0.1382 0.6603 11.00000 0.05 0.29 Q17 1 0.6816 0.3043 0.7562 11.00000 0.05 0.28 Q18 1 -0.0013 0.1614 0.7291 11.00000 0.05 0.25 Q19 1 0.5455 -0.1230 0.5951 11.00000 0.05 0.25 Q20 1 0.6570 0.0764 0.6256 11.00000 0.05 0.24 ; _shelx_res_checksum 21720 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_191108ueta_a _audit_block_doi 10.5517/ccdc.csd.cc26qjj0 _database_code_depnum_ccdc_archive 'CCDC 2047442' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1SC00044F 2021 loop_ _audit_author_name _audit_author_address 'Tomoyuki Yanagi' ;Kyoto university Japan ; _audit_update_record ; 2020-12-01 deposited with the CCDC. 2021-02-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H18 N2' _chemical_formula_sum 'C30 H18 N2' _chemical_formula_weight 406.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.99580(10) _cell_length_b 15.94920(10) _cell_length_c 7.81480(10) _cell_angle_alpha 90 _cell_angle_beta 91.5160(10) _cell_angle_gamma 90 _cell_volume 1993.02(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 19236 _cell_measurement_theta_min 2.7750 _cell_measurement_theta_max 72.7080 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_F_000 848 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.030 _exptl_absorpt_coefficient_mu 0.613 _shelx_estimated_absorpt_T_min 0.847 _shelx_estimated_absorpt_T_max 0.982 _exptl_absorpt_correction_T_min 0.73978 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 27002 _diffrn_reflns_av_unetI/netI 0.0111 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.763 _diffrn_reflns_theta_max 72.897 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 3935 _reflns_number_gt 3738 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.6572P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3935 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.19332(6) 0.29719(6) -0.02631(12) 0.0283(2) Uani 1 1 d . . . . . H1 H 0.1703 0.2643 -0.1047 0.034 Uiso 1 1 calc R U . . . N2 N 0.47444(6) 0.58172(7) 0.37356(13) 0.0323(2) Uani 1 1 d . . . . . H2 H 0.5201 0.6025 0.4225 0.039 Uiso 1 1 calc R U . . . C12 C 0.20990(7) 0.38063(6) 0.20652(14) 0.0220(2) Uani 1 1 d . . . . . C13 C 0.25644(7) 0.59809(7) 0.25718(13) 0.0225(2) Uani 1 1 d . . . . . C14 C 0.19996(7) 0.56740(7) 0.12953(14) 0.0230(2) Uani 1 1 d . . . . . H3 H 0.2169 0.5230 0.0572 0.028 Uiso 1 1 calc R U . . . C15 C 0.18516(7) 0.40933(6) 0.37168(14) 0.0222(2) Uani 1 1 d . . . . . C16 C 0.28768(7) 0.37934(7) 0.11547(13) 0.0227(2) Uani 1 1 d . . . . . C17 C 0.36799(7) 0.41873(7) 0.13634(13) 0.0235(2) Uani 1 1 d . . . . . C18 C 0.09922(7) 0.40090(7) 0.41316(15) 0.0250(2) Uani 1 1 d . . . . . C19 C 0.33942(7) 0.56630(7) 0.28669(13) 0.0236(2) Uani 1 1 d . . . . . C20 C 0.15276(7) 0.33211(7) 0.10906(14) 0.0251(2) Uani 1 1 d . . . . . C21 C 0.38679(7) 0.49490(7) 0.22660(14) 0.0241(2) Uani 1 1 d . . . . . C22 C 0.24166(7) 0.43853(7) 0.50074(14) 0.0242(2) Uani 1 1 d . . . . . H4 H 0.2996 0.4415 0.4780 0.029 Uiso 1 1 calc R U . . . C23 C 0.12118(7) 0.60051(7) 0.10820(14) 0.0266(2) Uani 1 1 d . . . . . H5 H 0.0841 0.5784 0.0226 0.032 Uiso 1 1 calc R U . . . C24 C 0.27554(7) 0.32176(7) -0.01974(14) 0.0264(2) Uani 1 1 d . . . . . C25 C 0.23138(8) 0.66909(7) 0.35463(14) 0.0273(2) Uani 1 1 d . . . . . C26 C 0.47091(7) 0.51075(8) 0.27426(14) 0.0288(3) Uani 1 1 d . . . . . C27 C 0.06814(7) 0.32238(7) 0.15158(16) 0.0293(3) Uani 1 1 d . . . . . H6 H 0.0306 0.2909 0.0806 0.035 Uiso 1 1 calc R U . . . C28 C 0.39563(7) 0.61537(8) 0.38478(15) 0.0286(3) Uani 1 1 d . . . . . C29 C 0.14951(8) 0.70090(7) 0.33086(15) 0.0308(3) Uani 1 1 d . . . . . H7 H 0.1320 0.7468 0.3986 0.037 Uiso 1 1 calc R U . . . C30 C 0.43638(7) 0.37734(7) 0.05736(15) 0.0283(3) Uani 1 1 d . . . . . C31 C 0.09504(8) 0.66703(7) 0.21235(15) 0.0300(3) Uani 1 1 d . . . . . H8 H 0.0397 0.6883 0.2003 0.036 Uiso 1 1 calc R U . . . C32 C 0.21409(8) 0.46259(8) 0.65821(15) 0.0301(3) Uani 1 1 d . . . . . H9 H 0.2531 0.4817 0.7432 0.036 Uiso 1 1 calc R U . . . C33 C 0.04182(7) 0.35960(7) 0.29791(16) 0.0289(3) Uani 1 1 d . . . . . H10 H -0.0159 0.3580 0.3237 0.035 Uiso 1 1 calc R U . . . C34 C 0.07267(7) 0.42886(7) 0.57466(16) 0.0299(3) Uani 1 1 d . . . . . H11 H 0.0150 0.4265 0.6003 0.036 Uiso 1 1 calc R U . . . C35 C 0.42025(8) 0.31486(8) -0.06982(16) 0.0324(3) Uani 1 1 d . . . . . H12 H 0.4663 0.2893 -0.1236 0.039 Uiso 1 1 calc R U . . . C36 C 0.12868(8) 0.45926(8) 0.69468(15) 0.0325(3) Uani 1 1 d . . . . . H13 H 0.1098 0.4781 0.8024 0.039 Uiso 1 1 calc R U . . . C37 C 0.37077(9) 0.68551(8) 0.48058(16) 0.0350(3) Uani 1 1 d . . . . . H14 H 0.4099 0.7150 0.5516 0.042 Uiso 1 1 calc R U . . . C38 C 0.52022(8) 0.40003(8) 0.10274(16) 0.0332(3) Uani 1 1 d . . . . . H15 H 0.5649 0.3706 0.0524 0.040 Uiso 1 1 calc R U . . . C39 C 0.34153(8) 0.29052(7) -0.11704(15) 0.0314(3) Uani 1 1 d . . . . . H16 H 0.3315 0.2541 -0.2115 0.038 Uiso 1 1 calc R U . . . C40 C 0.53814(7) 0.46270(9) 0.21621(16) 0.0343(3) Uani 1 1 d . . . . . H17 H 0.5939 0.4735 0.2547 0.041 Uiso 1 1 calc R U . . . C41 C 0.28960(9) 0.70982(8) 0.46883(16) 0.0340(3) Uani 1 1 d . . . . . H18 H 0.2711 0.7548 0.5379 0.041 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0357(5) 0.0216(5) 0.0274(5) -0.0050(4) -0.0022(4) -0.0025(4) N2 0.0274(5) 0.0389(6) 0.0304(5) -0.0002(4) -0.0033(4) -0.0102(4) C12 0.0248(5) 0.0160(5) 0.0251(5) 0.0022(4) -0.0006(4) 0.0004(4) C13 0.0291(5) 0.0181(5) 0.0205(5) 0.0024(4) 0.0045(4) -0.0028(4) C14 0.0291(5) 0.0170(5) 0.0229(5) 0.0009(4) 0.0029(4) -0.0007(4) C15 0.0253(5) 0.0160(5) 0.0252(5) 0.0038(4) 0.0012(4) 0.0011(4) C16 0.0274(5) 0.0187(5) 0.0220(5) 0.0012(4) 0.0008(4) 0.0026(4) C17 0.0259(5) 0.0233(5) 0.0213(5) 0.0028(4) 0.0019(4) 0.0029(4) C18 0.0249(5) 0.0191(5) 0.0309(6) 0.0050(4) 0.0013(4) 0.0009(4) C19 0.0284(5) 0.0226(5) 0.0201(5) 0.0009(4) 0.0027(4) -0.0059(4) C20 0.0304(6) 0.0182(5) 0.0267(5) 0.0013(4) -0.0023(4) -0.0005(4) C21 0.0243(5) 0.0266(6) 0.0214(5) 0.0029(4) 0.0018(4) -0.0019(4) C22 0.0260(5) 0.0225(5) 0.0242(5) 0.0032(4) 0.0011(4) -0.0020(4) C23 0.0303(6) 0.0230(5) 0.0265(5) 0.0035(4) 0.0008(4) 0.0003(4) C24 0.0346(6) 0.0197(5) 0.0249(5) 0.0004(4) 0.0005(4) 0.0016(4) C25 0.0393(6) 0.0205(5) 0.0223(5) 0.0007(4) 0.0056(5) -0.0019(5) C26 0.0270(6) 0.0342(6) 0.0252(5) 0.0037(5) -0.0001(4) -0.0043(5) C27 0.0280(6) 0.0238(6) 0.0358(6) 0.0024(5) -0.0066(5) -0.0054(4) C28 0.0318(6) 0.0289(6) 0.0252(5) 0.0018(4) -0.0001(4) -0.0081(5) C29 0.0427(7) 0.0218(6) 0.0282(6) -0.0007(4) 0.0097(5) 0.0054(5) C30 0.0292(6) 0.0284(6) 0.0274(6) 0.0047(4) 0.0046(4) 0.0057(5) C31 0.0336(6) 0.0260(6) 0.0309(6) 0.0048(5) 0.0066(5) 0.0071(5) C32 0.0346(6) 0.0314(6) 0.0243(6) 0.0008(5) 0.0003(5) -0.0027(5) C33 0.0238(5) 0.0247(6) 0.0381(6) 0.0055(5) -0.0011(5) -0.0017(4) C34 0.0278(6) 0.0276(6) 0.0346(6) 0.0055(5) 0.0073(5) 0.0019(4) C35 0.0383(6) 0.0280(6) 0.0313(6) 0.0012(5) 0.0096(5) 0.0102(5) C36 0.0371(6) 0.0342(7) 0.0265(6) -0.0001(5) 0.0085(5) 0.0019(5) C37 0.0464(7) 0.0285(6) 0.0298(6) -0.0042(5) -0.0037(5) -0.0127(5) C38 0.0276(6) 0.0386(7) 0.0338(6) 0.0069(5) 0.0065(5) 0.0073(5) C39 0.0431(7) 0.0238(6) 0.0276(6) -0.0033(4) 0.0047(5) 0.0050(5) C40 0.0231(6) 0.0451(7) 0.0347(6) 0.0078(5) 0.0005(5) -0.0005(5) C41 0.0502(7) 0.0235(6) 0.0284(6) -0.0058(5) 0.0027(5) -0.0036(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C24 1.3719(15) . ? N1 C20 1.3735(15) . ? N1 H1 0.8800 . ? N2 C26 1.3727(16) . ? N2 C28 1.3752(16) . ? N2 H2 0.8800 . ? C12 C20 1.4062(15) . ? C12 C15 1.4350(15) . ? C12 C16 1.4497(15) . ? C13 C14 1.4154(15) . ? C13 C25 1.4279(15) . ? C13 C19 1.4338(16) . ? C14 C23 1.3724(16) . ? C14 H3 0.9500 . ? C15 C22 1.4151(15) . ? C15 C18 1.4270(15) . ? C16 C24 1.4096(15) . ? C16 C17 1.4353(15) . ? C17 C30 1.4316(15) . ? C17 C21 1.4327(16) . ? C18 C34 1.4144(16) . ? C18 C33 1.4298(16) . ? C19 C28 1.4043(15) . ? C19 C21 1.4527(16) . ? C20 C27 1.4108(16) . ? C21 C26 1.4094(15) . ? C22 C32 1.3730(16) . ? C22 H4 0.9500 . ? C23 C31 1.4074(16) . ? C23 H5 0.9500 . ? C24 C39 1.4082(16) . ? C25 C29 1.4121(17) . ? C25 C41 1.4289(17) . ? C26 C40 1.4054(17) . ? C27 C33 1.3649(18) . ? C27 H6 0.9500 . ? C28 C37 1.4092(18) . ? C29 C31 1.3660(18) . ? C29 H7 0.9500 . ? C30 C38 1.4247(17) . ? C30 C35 1.4262(17) . ? C31 H8 0.9500 . ? C32 C36 1.4040(17) . ? C32 H9 0.9500 . ? C33 H10 0.9500 . ? C34 C36 1.3686(18) . ? C34 H11 0.9500 . ? C35 C39 1.3594(18) . ? C35 H12 0.9500 . ? C36 H13 0.9500 . ? C37 C41 1.3559(19) . ? C37 H14 0.9500 . ? C38 C40 1.3616(19) . ? C38 H15 0.9500 . ? C39 H16 0.9500 . ? C40 H17 0.9500 . ? C41 H18 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C24 N1 C20 109.10(9) . . ? C24 N1 H1 125.4 . . ? C20 N1 H1 125.4 . . ? C26 N2 C28 109.50(9) . . ? C26 N2 H2 125.3 . . ? C28 N2 H2 125.3 . . ? C20 C12 C15 118.16(10) . . ? C20 C12 C16 106.28(9) . . ? C15 C12 C16 134.97(10) . . ? C14 C13 C25 117.85(10) . . ? C14 C13 C19 124.19(10) . . ? C25 C13 C19 117.81(10) . . ? C23 C14 C13 121.30(10) . . ? C23 C14 H3 119.4 . . ? C13 C14 H3 119.4 . . ? C22 C15 C18 118.03(10) . . ? C22 C15 C12 124.05(10) . . ? C18 C15 C12 117.68(10) . . ? C24 C16 C17 118.39(10) . . ? C24 C16 C12 105.91(9) . . ? C17 C16 C12 135.66(10) . . ? C30 C17 C21 116.77(10) . . ? C30 C17 C16 116.17(10) . . ? C21 C17 C16 127.06(10) . . ? C34 C18 C15 119.13(10) . . ? C34 C18 C33 120.29(10) . . ? C15 C18 C33 120.45(10) . . ? C28 C19 C13 117.86(10) . . ? C28 C19 C21 106.34(10) . . ? C13 C19 C21 135.55(10) . . ? N1 C20 C12 109.07(10) . . ? N1 C20 C27 127.77(10) . . ? C12 C20 C27 123.15(11) . . ? C26 C21 C17 117.95(10) . . ? C26 C21 C19 106.05(10) . . ? C17 C21 C19 135.99(10) . . ? C32 C22 C15 121.10(10) . . ? C32 C22 H4 119.5 . . ? C15 C22 H4 119.5 . . ? C14 C23 C31 120.38(11) . . ? C14 C23 H5 119.8 . . ? C31 C23 H5 119.8 . . ? N1 C24 C39 127.61(11) . . ? N1 C24 C16 109.09(10) . . ? C39 C24 C16 123.02(11) . . ? C29 C25 C13 119.16(10) . . ? C29 C25 C41 120.37(11) . . ? C13 C25 C41 120.40(11) . . ? N2 C26 C40 127.71(11) . . ? N2 C26 C21 108.79(10) . . ? C40 C26 C21 123.38(11) . . ? C33 C27 C20 117.95(10) . . ? C33 C27 H6 121.0 . . ? C20 C27 H6 121.0 . . ? N2 C28 C19 108.81(10) . . ? N2 C28 C37 128.01(11) . . ? C19 C28 C37 123.15(11) . . ? C31 C29 C25 121.31(11) . . ? C31 C29 H7 119.3 . . ? C25 C29 H7 119.3 . . ? C38 C30 C35 120.18(11) . . ? C38 C30 C17 120.04(11) . . ? C35 C30 C17 119.76(11) . . ? C29 C31 C23 119.76(11) . . ? C29 C31 H8 120.1 . . ? C23 C31 H8 120.1 . . ? C22 C32 C36 120.59(11) . . ? C22 C32 H9 119.7 . . ? C36 C32 H9 119.7 . . ? C27 C33 C18 121.39(10) . . ? C27 C33 H10 119.3 . . ? C18 C33 H10 119.3 . . ? C36 C34 C18 121.11(11) . . ? C36 C34 H11 119.4 . . ? C18 C34 H11 119.4 . . ? C39 C35 C30 122.54(11) . . ? C39 C35 H12 118.7 . . ? C30 C35 H12 118.7 . . ? C34 C36 C32 119.81(11) . . ? C34 C36 H13 120.1 . . ? C32 C36 H13 120.1 . . ? C41 C37 C28 118.30(11) . . ? C41 C37 H14 120.8 . . ? C28 C37 H14 120.8 . . ? C40 C38 C30 121.94(11) . . ? C40 C38 H15 119.0 . . ? C30 C38 H15 119.0 . . ? C35 C39 C24 117.04(11) . . ? C35 C39 H16 121.5 . . ? C24 C39 H16 121.5 . . ? C38 C40 C26 117.44(11) . . ? C38 C40 H17 121.3 . . ? C26 C40 H17 121.3 . . ? C37 C41 C25 121.30(11) . . ? C37 C41 H18 119.4 . . ? C25 C41 H18 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C25 C13 C14 C23 -4.80(15) . . . . ? C19 C13 C14 C23 179.84(10) . . . . ? C20 C12 C15 C22 162.46(10) . . . . ? C16 C12 C15 C22 -7.32(19) . . . . ? C20 C12 C15 C18 -11.80(14) . . . . ? C16 C12 C15 C18 178.42(11) . . . . ? C20 C12 C16 C24 -7.07(11) . . . . ? C15 C12 C16 C24 163.55(11) . . . . ? C20 C12 C16 C17 175.43(12) . . . . ? C15 C12 C16 C17 -14.0(2) . . . . ? C24 C16 C17 C30 -20.06(15) . . . . ? C12 C16 C17 C30 157.21(12) . . . . ? C24 C16 C17 C21 159.60(11) . . . . ? C12 C16 C17 C21 -23.1(2) . . . . ? C22 C15 C18 C34 5.63(15) . . . . ? C12 C15 C18 C34 -179.76(10) . . . . ? C22 C15 C18 C33 -170.15(10) . . . . ? C12 C15 C18 C33 4.47(15) . . . . ? C14 C13 C19 C28 163.84(10) . . . . ? C25 C13 C19 C28 -11.52(15) . . . . ? C14 C13 C19 C21 -9.48(19) . . . . ? C25 C13 C19 C21 175.16(11) . . . . ? C24 N1 C20 C12 -0.04(12) . . . . ? C24 N1 C20 C27 -179.23(11) . . . . ? C15 C12 C20 N1 -168.01(9) . . . . ? C16 C12 C20 N1 4.48(12) . . . . ? C15 C12 C20 C27 11.24(16) . . . . ? C16 C12 C20 C27 -176.28(10) . . . . ? C30 C17 C21 C26 -18.12(15) . . . . ? C16 C17 C21 C26 162.22(11) . . . . ? C30 C17 C21 C19 161.45(12) . . . . ? C16 C17 C21 C19 -18.2(2) . . . . ? C28 C19 C21 C26 -7.17(12) . . . . ? C13 C19 C21 C26 166.68(12) . . . . ? C28 C19 C21 C17 173.22(12) . . . . ? C13 C19 C21 C17 -12.9(2) . . . . ? C18 C15 C22 C32 -3.63(16) . . . . ? C12 C15 C22 C32 -177.87(10) . . . . ? C13 C14 C23 C31 0.82(16) . . . . ? C20 N1 C24 C39 169.36(11) . . . . ? C20 N1 C24 C16 -4.62(13) . . . . ? C17 C16 C24 N1 -174.75(9) . . . . ? C12 C16 C24 N1 7.23(12) . . . . ? C17 C16 C24 C39 10.93(16) . . . . ? C12 C16 C24 C39 -167.08(10) . . . . ? C14 C13 C25 C29 5.53(15) . . . . ? C19 C13 C25 C29 -178.81(10) . . . . ? C14 C13 C25 C41 -171.56(10) . . . . ? C19 C13 C25 C41 4.10(16) . . . . ? C28 N2 C26 C40 172.78(12) . . . . ? C28 N2 C26 C21 -3.20(13) . . . . ? C17 C21 C26 N2 -173.90(9) . . . . ? C19 C21 C26 N2 6.41(12) . . . . ? C17 C21 C26 C40 9.91(17) . . . . ? C19 C21 C26 C40 -169.78(11) . . . . ? N1 C20 C27 C33 176.65(11) . . . . ? C12 C20 C27 C33 -2.44(17) . . . . ? C26 N2 C28 C19 -1.51(13) . . . . ? C26 N2 C28 C37 176.60(12) . . . . ? C13 C19 C28 N2 -169.72(9) . . . . ? C21 C19 C28 N2 5.42(12) . . . . ? C13 C19 C28 C37 12.06(17) . . . . ? C21 C19 C28 C37 -172.81(11) . . . . ? C13 C25 C29 C31 -2.40(17) . . . . ? C41 C25 C29 C31 174.70(11) . . . . ? C21 C17 C30 C38 14.78(16) . . . . ? C16 C17 C30 C38 -165.52(10) . . . . ? C21 C17 C30 C35 -163.67(10) . . . . ? C16 C17 C30 C35 16.02(16) . . . . ? C25 C29 C31 C23 -1.68(18) . . . . ? C14 C23 C31 C29 2.52(17) . . . . ? C15 C22 C32 C36 -0.40(18) . . . . ? C20 C27 C33 C18 -5.50(17) . . . . ? C34 C18 C33 C27 -171.30(11) . . . . ? C15 C18 C33 C27 4.43(17) . . . . ? C15 C18 C34 C36 -3.76(17) . . . . ? C33 C18 C34 C36 172.02(11) . . . . ? C38 C30 C35 C39 179.56(11) . . . . ? C17 C30 C35 C39 -1.99(18) . . . . ? C18 C34 C36 C32 -0.31(18) . . . . ? C22 C32 C36 C34 2.44(18) . . . . ? N2 C28 C37 C41 177.87(12) . . . . ? C19 C28 C37 C41 -4.27(18) . . . . ? C35 C30 C38 C40 176.14(12) . . . . ? C17 C30 C38 C40 -2.31(18) . . . . ? C30 C35 C39 C24 -7.92(18) . . . . ? N1 C24 C39 C35 -169.81(11) . . . . ? C16 C24 C39 C35 3.40(17) . . . . ? C30 C38 C40 C26 -6.60(18) . . . . ? N2 C26 C40 C38 -172.69(12) . . . . ? C21 C26 C40 C38 2.75(18) . . . . ? C28 C37 C41 C25 -3.84(19) . . . . ? C29 C25 C41 C37 -173.25(12) . . . . ? C13 C25 C41 C37 3.81(18) . . . . ? _refine_diff_density_max 0.159 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.047 _shelx_res_file ; 191108ueta_a.res created by SHELXL-2014/7 TITL 191108ueta_a.res in P2(1)/c REM Yadorkari-X generated CELL 1.54184 15.9958 15.9492 7.8148 90.0000 91.5160 90.0000 ZERR 4.0 0.0001 0.0001 0.0001 0.0000 0.0010 0.0000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z REM SPGR P21/c monoclinic SFAC C H N UNIT 120 72 8 SIZE 0.28 0.17 0.03 TEMP -180.0 L.S. 10 FMAP 2 PLAN -20 ACTA CONF HTAB LIST 4 BOND $H MERG 2 WGHT 0.048200 0.657200 FVAR 0.55760 N1 3 0.193324 0.297192 -0.026309 11.00000 0.03569 0.02164 = 0.02736 -0.00502 -0.00222 -0.00255 AFIX 43 H1 2 0.170261 0.264323 -0.104716 11.00000 -1.20000 AFIX 0 N2 3 0.474445 0.581716 0.373558 11.00000 0.02739 0.03891 = 0.03039 -0.00020 -0.00328 -0.01020 AFIX 43 H2 2 0.520103 0.602474 0.422483 11.00000 -1.20000 AFIX 0 C12 1 0.209902 0.380630 0.206516 11.00000 0.02478 0.01600 = 0.02509 0.00219 -0.00064 0.00038 C13 1 0.256442 0.598091 0.257184 11.00000 0.02910 0.01812 = 0.02052 0.00238 0.00448 -0.00280 C14 1 0.199956 0.567398 0.129534 11.00000 0.02908 0.01697 = 0.02295 0.00087 0.00290 -0.00068 AFIX 43 H3 2 0.216908 0.523001 0.057208 11.00000 -1.20000 AFIX 0 C15 1 0.185162 0.409330 0.371679 11.00000 0.02532 0.01599 = 0.02522 0.00382 0.00123 0.00112 C16 1 0.287685 0.379343 0.115472 11.00000 0.02740 0.01871 = 0.02202 0.00124 0.00083 0.00262 C17 1 0.367986 0.418734 0.136338 11.00000 0.02586 0.02333 = 0.02133 0.00280 0.00194 0.00287 C18 1 0.099222 0.400904 0.413159 11.00000 0.02494 0.01914 = 0.03086 0.00495 0.00130 0.00089 C19 1 0.339419 0.566298 0.286689 11.00000 0.02841 0.02259 = 0.02005 0.00090 0.00270 -0.00594 C20 1 0.152765 0.332107 0.109063 11.00000 0.03036 0.01820 = 0.02670 0.00132 -0.00226 -0.00046 C21 1 0.386794 0.494901 0.226599 11.00000 0.02429 0.02664 = 0.02137 0.00291 0.00177 -0.00190 C22 1 0.241664 0.438527 0.500736 11.00000 0.02601 0.02254 = 0.02421 0.00323 0.00112 -0.00195 AFIX 43 H4 2 0.299640 0.441526 0.478033 11.00000 -1.20000 AFIX 0 C23 1 0.121178 0.600514 0.108195 11.00000 0.03033 0.02295 = 0.02650 0.00349 0.00076 0.00033 AFIX 43 H5 2 0.084079 0.578413 0.022634 11.00000 -1.20000 AFIX 0 C24 1 0.275544 0.321755 -0.019741 11.00000 0.03457 0.01966 = 0.02489 0.00043 0.00053 0.00162 C25 1 0.231376 0.669087 0.354631 11.00000 0.03932 0.02046 = 0.02225 0.00070 0.00561 -0.00189 C26 1 0.470909 0.510745 0.274262 11.00000 0.02704 0.03418 = 0.02524 0.00369 -0.00014 -0.00428 C27 1 0.068144 0.322377 0.151583 11.00000 0.02796 0.02380 = 0.03582 0.00236 -0.00665 -0.00539 AFIX 43 H6 2 0.030643 0.290889 0.080557 11.00000 -1.20000 AFIX 0 C28 1 0.395628 0.615370 0.384784 11.00000 0.03175 0.02890 = 0.02517 0.00179 -0.00010 -0.00812 C29 1 0.149508 0.700904 0.330858 11.00000 0.04268 0.02184 = 0.02820 -0.00068 0.00972 0.00538 AFIX 43 H7 2 0.131962 0.746780 0.398632 11.00000 -1.20000 AFIX 0 C30 1 0.436383 0.377342 0.057361 11.00000 0.02923 0.02842 = 0.02737 0.00471 0.00463 0.00567 C31 1 0.095040 0.667033 0.212348 11.00000 0.03355 0.02599 = 0.03088 0.00483 0.00661 0.00710 AFIX 43 H8 2 0.039722 0.688297 0.200276 11.00000 -1.20000 AFIX 0 C32 1 0.214090 0.462592 0.658209 11.00000 0.03461 0.03142 = 0.02426 0.00077 0.00028 -0.00267 AFIX 43 H9 2 0.253148 0.481665 0.743243 11.00000 -1.20000 AFIX 0 C33 1 0.041819 0.359602 0.297912 11.00000 0.02378 0.02468 = 0.03810 0.00546 -0.00106 -0.00174 AFIX 43 H10 2 -0.015862 0.358036 0.323735 11.00000 -1.20000 AFIX 0 C34 1 0.072669 0.428864 0.574663 11.00000 0.02780 0.02755 = 0.03460 0.00550 0.00726 0.00190 AFIX 43 H11 2 0.014987 0.426503 0.600255 11.00000 -1.20000 AFIX 0 C35 1 0.420251 0.314858 -0.069822 11.00000 0.03829 0.02800 = 0.03129 0.00122 0.00965 0.01022 AFIX 43 H12 2 0.466302 0.289257 -0.123625 11.00000 -1.20000 AFIX 0 C36 1 0.128680 0.459262 0.694685 11.00000 0.03712 0.03424 = 0.02649 -0.00010 0.00855 0.00193 AFIX 43 H13 2 0.109821 0.478057 0.802372 11.00000 -1.20000 AFIX 0 C37 1 0.370773 0.685511 0.480582 11.00000 0.04638 0.02847 = 0.02980 -0.00424 -0.00374 -0.01270 AFIX 43 H14 2 0.409894 0.715015 0.551583 11.00000 -1.20000 AFIX 0 C38 1 0.520220 0.400028 0.102744 11.00000 0.02762 0.03860 = 0.03376 0.00688 0.00652 0.00727 AFIX 43 H15 2 0.564938 0.370561 0.052356 11.00000 -1.20000 AFIX 0 C39 1 0.341529 0.290516 -0.117040 11.00000 0.04307 0.02375 = 0.02762 -0.00331 0.00466 0.00504 AFIX 43 H16 2 0.331478 0.254050 -0.211479 11.00000 -1.20000 AFIX 0 C40 1 0.538136 0.462697 0.216208 11.00000 0.02314 0.04509 = 0.03468 0.00778 0.00047 -0.00046 AFIX 43 H17 2 0.593933 0.473527 0.254653 11.00000 -1.20000 AFIX 0 C41 1 0.289598 0.709816 0.468834 11.00000 0.05023 0.02352 = 0.02843 -0.00583 0.00267 -0.00364 AFIX 43 H18 2 0.271065 0.754809 0.537888 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 191108ueta_a.res in P2(1)/c REM R1 = 0.0380 for 3738 Fo > 4sig(Fo) and 0.0394 for all 3935 data REM 289 parameters refined using 0 restraints END WGHT 0.0482 0.6572 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.159, deepest hole -0.270, 1-sigma level 0.047 Q1 1 0.3567 0.5789 0.3791 11.00000 0.05 0.16 Q2 1 0.3199 0.4072 0.1243 11.00000 0.05 0.14 Q3 1 0.2458 0.4035 0.1609 11.00000 0.05 0.13 Q4 1 0.2977 0.5757 0.2723 11.00000 0.05 0.13 Q5 1 0.3556 0.5260 0.2494 11.00000 0.05 0.12 Q6 1 0.2664 0.7854 0.4936 11.00000 0.05 0.12 Q7 1 0.1989 0.4057 0.2867 11.00000 0.05 0.11 Q8 1 0.6018 0.5167 0.2560 11.00000 0.05 0.11 Q9 1 -0.0208 0.3420 0.3829 11.00000 0.05 0.11 Q10 1 0.2811 0.3653 0.0288 11.00000 0.05 0.11 Q11 1 0.3208 0.2189 -0.1830 11.00000 0.05 0.11 Q12 1 0.0482 0.3671 0.1944 11.00000 0.05 0.11 Q13 1 0.2431 0.6359 0.2992 11.00000 0.05 0.11 Q14 1 0.2415 0.4163 0.6030 11.00000 0.05 0.10 Q15 1 0.4284 0.4976 0.2512 11.00000 0.05 0.10 Q16 1 0.1158 0.4486 0.8637 11.00000 0.05 0.10 Q17 1 0.2781 0.4333 0.7733 11.00000 0.05 0.10 Q18 1 0.4022 0.3936 0.0981 11.00000 0.05 0.10 Q19 1 0.1366 0.7022 0.2336 11.00000 0.05 0.10 Q20 1 0.0901 0.4619 0.1562 11.00000 0.05 0.10 ; _shelx_res_checksum 58225 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_9931yng_a _audit_block_doi 10.5517/ccdc.csd.cc26qjgy _database_code_depnum_ccdc_archive 'CCDC 2047440' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1SC00044F 2021 loop_ _audit_author_name _audit_author_address 'Tomoyuki Yanagi' ;Kyoto university Japan ; _audit_update_record ; 2020-12-01 deposited with the CCDC. 2021-02-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H16 S2' _chemical_formula_sum 'C30 H16 S2' _chemical_formula_weight 440.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.338(3) _cell_length_b 13.622(3) _cell_length_c 16.299(4) _cell_angle_alpha 90 _cell_angle_beta 102.204(7) _cell_angle_gamma 90 _cell_volume 2026.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2447 _cell_measurement_theta_min 25.4 _cell_measurement_theta_max 69.0 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_F_000 912 _exptl_transmission_factor_min 0.543 _exptl_transmission_factor_max 0.688 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.150 _exptl_absorpt_coefficient_mu 2.497 _shelx_estimated_absorpt_T_min 0.542 _shelx_estimated_absorpt_T_max 0.706 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 53850 _diffrn_reflns_av_unetI/netI 0.0159 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 6.894 _diffrn_reflns_theta_max 69.098 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_point_group_measured_fraction_full 0.997 _reflns_number_total 3750 _reflns_number_gt 3666 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+1.3066P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3750 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.24588(17) 0.31948(10) 0.12003(8) 0.0169(3) Uani 1 1 d . . . . . H1 H 0.1777 0.2881 0.0764 0.020 Uiso 1 1 calc R U . . . C2 C 0.39212(17) 0.31466(10) 0.12014(9) 0.0179(3) Uani 1 1 d . . . . . H2 H 0.4248 0.2806 0.0766 0.021 Uiso 1 1 calc R U . . . C3 C 0.49410(17) 0.36010(10) 0.18472(9) 0.0166(3) Uani 1 1 d . . . . . H3 H 0.5959 0.3550 0.1857 0.020 Uiso 1 1 calc R U . . . C4 C 0.44736(15) 0.41187(9) 0.24649(8) 0.0128(3) Uani 1 1 d . . . . . H4 H 0.5176 0.4419 0.2899 0.015 Uiso 1 1 calc R U . . . C5 C 0.29657(15) 0.42137(9) 0.24658(8) 0.0118(3) Uani 1 1 d . . . . . C6 C 0.19425(16) 0.37044(10) 0.18366(8) 0.0141(3) Uani 1 1 d . . . . . C7 C 0.04349(16) 0.36576(10) 0.18764(9) 0.0167(3) Uani 1 1 d . . . . . H7 H -0.0244 0.3354 0.1433 0.020 Uiso 1 1 calc R U . . . C8 C -0.00472(16) 0.40407(10) 0.25389(9) 0.0170(3) Uani 1 1 d . . . . . H8 H -0.1034 0.3954 0.2590 0.020 Uiso 1 1 calc R U . . . C9 C 0.09559(15) 0.45703(10) 0.31489(8) 0.0141(3) Uani 1 1 d . . . . . C10 C 0.24053(15) 0.47507(10) 0.30913(8) 0.0118(3) Uani 1 1 d . . . . . C11 C 0.31184(15) 0.54272(10) 0.37408(8) 0.0116(3) Uani 1 1 d . . . . . C12 C 0.22678(15) 0.55664(10) 0.43442(8) 0.0135(3) Uani 1 1 d . . . . . C13 C 0.28013(16) 0.60295(10) 0.51222(8) 0.0157(3) Uani 1 1 d . . . . . H13 H 0.2188 0.6130 0.5511 0.019 Uiso 1 1 calc R U . . . C14 C 0.42217(16) 0.63282(10) 0.52970(8) 0.0156(3) Uani 1 1 d . . . . . H14 H 0.4644 0.6557 0.5845 0.019 Uiso 1 1 calc R U . . . C15 C 0.50919(15) 0.63062(10) 0.46790(8) 0.0132(3) Uani 1 1 d . . . . . C16 C 0.44732(15) 0.59677(9) 0.38479(8) 0.0115(3) Uani 1 1 d . . . . . C17 C 0.52600(15) 0.62079(10) 0.32057(8) 0.0121(3) Uani 1 1 d . . . . . C18 C 0.67523(15) 0.64415(10) 0.34700(9) 0.0146(3) Uani 1 1 d . . . . . C19 C 0.74212(16) 0.66476(10) 0.43102(9) 0.0163(3) Uani 1 1 d . . . . . H19 H 0.8438 0.6791 0.4468 0.020 Uiso 1 1 calc R U . . . C20 C 0.65665(16) 0.66354(10) 0.48880(8) 0.0155(3) Uani 1 1 d . . . . . H20 H 0.6963 0.6852 0.5444 0.019 Uiso 1 1 calc R U . . . C21 C 0.48218(15) 0.62283(10) 0.22923(8) 0.0125(3) Uani 1 1 d . . . . . C22 C 0.60411(16) 0.62982(10) 0.19251(9) 0.0158(3) Uani 1 1 d . . . . . C23 C 0.59554(17) 0.61960(11) 0.10546(9) 0.0199(3) Uani 1 1 d . . . . . H23 H 0.6809 0.6245 0.0827 0.024 Uiso 1 1 calc R U . . . C24 C 0.46224(17) 0.60252(11) 0.05491(9) 0.0191(3) Uani 1 1 d . . . . . H24 H 0.4559 0.5888 -0.0029 0.023 Uiso 1 1 calc R U . . . C25 C 0.33208(16) 0.60480(10) 0.08719(8) 0.0150(3) Uani 1 1 d . . . . . C26 C 0.33991(15) 0.62308(9) 0.17404(8) 0.0124(3) Uani 1 1 d . . . . . C27 C 0.20795(15) 0.64404(10) 0.20000(8) 0.0134(3) Uani 1 1 d . . . . . H27 H 0.2112 0.6638 0.2563 0.016 Uiso 1 1 calc R U . . . C28 C 0.07496(16) 0.63614(10) 0.14479(9) 0.0166(3) Uani 1 1 d . . . . . H28 H -0.0125 0.6508 0.1633 0.020 Uiso 1 1 calc R U . . . C29 C 0.06689(17) 0.60660(11) 0.06140(9) 0.0187(3) Uani 1 1 d . . . . . H29 H -0.0256 0.5961 0.0249 0.022 Uiso 1 1 calc R U . . . C30 C 0.19329(17) 0.59313(10) 0.03315(9) 0.0179(3) Uani 1 1 d . . . . . H30 H 0.1878 0.5756 -0.0238 0.022 Uiso 1 1 calc R U . . . S1 S 0.05237(4) 0.50720(3) 0.40416(2) 0.01600(11) Uani 1 1 d . . . . . S2 S 0.76627(4) 0.64907(3) 0.26493(2) 0.01910(11) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0265(8) 0.0121(6) 0.0103(6) 0.0004(5) -0.0002(5) -0.0035(6) C2 0.0289(8) 0.0127(7) 0.0131(6) -0.0014(5) 0.0067(6) 0.0002(6) C3 0.0209(8) 0.0136(7) 0.0161(7) 0.0013(5) 0.0059(6) 0.0017(5) C4 0.0169(7) 0.0096(6) 0.0109(6) 0.0013(5) 0.0003(5) -0.0002(5) C5 0.0170(7) 0.0088(6) 0.0088(6) 0.0028(5) 0.0010(5) -0.0004(5) C6 0.0198(7) 0.0097(6) 0.0111(6) 0.0029(5) -0.0002(5) -0.0013(5) C7 0.0184(7) 0.0136(7) 0.0147(7) 0.0020(5) -0.0038(5) -0.0040(5) C8 0.0134(7) 0.0179(7) 0.0181(7) 0.0040(6) -0.0005(5) -0.0027(5) C9 0.0149(7) 0.0144(7) 0.0126(6) 0.0032(5) 0.0018(5) 0.0010(5) C10 0.0135(7) 0.0113(6) 0.0093(6) 0.0031(5) -0.0006(5) 0.0011(5) C11 0.0141(7) 0.0112(6) 0.0086(6) 0.0025(5) 0.0003(5) 0.0031(5) C12 0.0151(7) 0.0131(6) 0.0118(6) 0.0035(5) 0.0020(5) 0.0025(5) C13 0.0228(8) 0.0154(7) 0.0095(6) 0.0024(5) 0.0050(5) 0.0045(6) C14 0.0252(8) 0.0121(6) 0.0078(6) 0.0008(5) -0.0007(5) 0.0027(6) C15 0.0178(7) 0.0090(6) 0.0107(6) 0.0005(5) -0.0016(5) 0.0028(5) C16 0.0135(7) 0.0096(6) 0.0104(6) 0.0002(5) 0.0000(5) 0.0031(5) C17 0.0134(7) 0.0094(6) 0.0124(6) -0.0010(5) 0.0004(5) 0.0016(5) C18 0.0144(7) 0.0126(6) 0.0163(7) -0.0005(5) 0.0019(5) 0.0007(5) C19 0.0133(7) 0.0139(7) 0.0186(7) -0.0017(5) -0.0036(5) 0.0000(5) C20 0.0197(7) 0.0113(6) 0.0119(6) -0.0009(5) -0.0047(5) 0.0022(5) C21 0.0158(7) 0.0097(6) 0.0120(6) -0.0011(5) 0.0033(5) -0.0006(5) C22 0.0160(7) 0.0154(7) 0.0163(7) -0.0006(5) 0.0043(6) -0.0012(5) C23 0.0222(8) 0.0231(7) 0.0171(7) -0.0006(6) 0.0102(6) -0.0013(6) C24 0.0286(8) 0.0187(7) 0.0112(6) -0.0004(5) 0.0069(6) -0.0001(6) C25 0.0214(8) 0.0108(6) 0.0122(6) 0.0010(5) 0.0020(5) -0.0008(5) C26 0.0167(7) 0.0082(6) 0.0115(6) 0.0013(5) 0.0015(5) -0.0014(5) C27 0.0175(7) 0.0111(6) 0.0112(6) 0.0021(5) 0.0020(5) 0.0005(5) C28 0.0164(7) 0.0156(7) 0.0168(7) 0.0045(5) 0.0013(6) 0.0008(5) C29 0.0201(8) 0.0166(7) 0.0154(7) 0.0039(5) -0.0051(6) -0.0017(6) C30 0.0279(8) 0.0146(7) 0.0092(6) 0.0008(5) -0.0007(6) -0.0017(6) S1 0.01407(19) 0.02161(19) 0.01290(18) 0.00152(13) 0.00416(13) 0.00034(13) S2 0.01317(19) 0.0258(2) 0.01872(19) -0.00295(14) 0.00431(14) -0.00336(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.367(2) . ? C1 C6 1.415(2) . ? C1 H1 0.9500 . ? C2 C3 1.405(2) . ? C2 H2 0.9500 . ? C3 C4 1.374(2) . ? C3 H3 0.9500 . ? C4 C5 1.414(2) . ? C4 H4 0.9500 . ? C5 C6 1.4254(19) . ? C5 C10 1.4402(19) . ? C6 C7 1.424(2) . ? C7 C8 1.359(2) . ? C7 H7 0.9500 . ? C8 C9 1.412(2) . ? C8 H8 0.9500 . ? C9 C10 1.398(2) . ? C9 S1 1.7307(14) . ? C10 C11 1.4544(19) . ? C11 C12 1.4015(19) . ? C11 C16 1.442(2) . ? C12 C13 1.4097(19) . ? C12 S1 1.7348(15) . ? C13 C14 1.359(2) . ? C13 H13 0.9500 . ? C14 C15 1.422(2) . ? C14 H14 0.9500 . ? C15 C20 1.419(2) . ? C15 C16 1.4320(18) . ? C16 C17 1.4378(19) . ? C17 C18 1.405(2) . ? C17 C21 1.4584(19) . ? C18 C19 1.408(2) . ? C18 S2 1.7313(15) . ? C19 C20 1.357(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.397(2) . ? C21 C26 1.4384(19) . ? C22 C23 1.411(2) . ? C22 S2 1.7318(15) . ? C23 C24 1.360(2) . ? C23 H23 0.9500 . ? C24 C25 1.423(2) . ? C24 H24 0.9500 . ? C25 C30 1.414(2) . ? C25 C26 1.4238(19) . ? C26 C27 1.414(2) . ? C27 C28 1.375(2) . ? C27 H27 0.9500 . ? C28 C29 1.404(2) . ? C28 H28 0.9500 . ? C29 C30 1.367(2) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.19(13) . . ? C2 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? C1 C2 C3 119.91(13) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.34(14) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 121.22(13) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 118.09(12) . . ? C4 C5 C10 123.92(12) . . ? C6 C5 C10 117.90(13) . . ? C1 C6 C7 120.31(13) . . ? C1 C6 C5 119.07(13) . . ? C7 C6 C5 120.51(13) . . ? C8 C7 C6 121.04(13) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 118.29(13) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 123.39(13) . . ? C10 C9 S1 112.84(10) . . ? C8 C9 S1 123.78(11) . . ? C9 C10 C5 117.39(12) . . ? C9 C10 C11 111.30(12) . . ? C5 C10 C11 131.16(13) . . ? C12 C11 C16 117.31(12) . . ? C12 C11 C10 110.87(12) . . ? C16 C11 C10 131.80(12) . . ? C11 C12 C13 123.15(13) . . ? C11 C12 S1 112.66(10) . . ? C13 C12 S1 124.16(11) . . ? C14 C13 C12 117.79(13) . . ? C14 C13 H13 121.1 . . ? C12 C13 H13 121.1 . . ? C13 C14 C15 121.60(13) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C20 C15 C14 119.61(12) . . ? C20 C15 C16 120.38(13) . . ? C14 C15 C16 120.01(13) . . ? C15 C16 C17 116.70(12) . . ? C15 C16 C11 116.55(12) . . ? C17 C16 C11 126.75(12) . . ? C18 C17 C16 117.04(12) . . ? C18 C17 C21 110.77(12) . . ? C16 C17 C21 132.15(12) . . ? C17 C18 C19 123.40(13) . . ? C17 C18 S2 112.90(10) . . ? C19 C18 S2 123.66(11) . . ? C20 C19 C18 117.86(13) . . ? C20 C19 H19 121.1 . . ? C18 C19 H19 121.1 . . ? C19 C20 C15 121.35(13) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C22 C21 C26 117.42(12) . . ? C22 C21 C17 111.13(12) . . ? C26 C21 C17 131.39(12) . . ? C21 C22 C23 123.09(13) . . ? C21 C22 S2 113.12(11) . . ? C23 C22 S2 123.77(11) . . ? C24 C23 C22 118.44(14) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C23 C24 C25 121.08(13) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C30 C25 C24 120.62(13) . . ? C30 C25 C26 119.13(13) . . ? C24 C25 C26 120.19(13) . . ? C27 C26 C25 117.90(13) . . ? C27 C26 C21 124.16(12) . . ? C25 C26 C21 117.90(13) . . ? C28 C27 C26 120.80(13) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 120.80(14) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C30 C29 C28 119.40(13) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C29 C30 C25 121.22(13) . . ? C29 C30 H30 119.4 . . ? C25 C30 H30 119.4 . . ? C9 S1 C12 91.18(7) . . ? C18 S2 C22 91.10(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.6(2) . . . . ? C1 C2 C3 C4 -1.9(2) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C3 C4 C5 C6 3.92(19) . . . . ? C3 C4 C5 C10 -179.61(13) . . . . ? C2 C1 C6 C7 -173.17(13) . . . . ? C2 C1 C6 C5 3.0(2) . . . . ? C4 C5 C6 C1 -5.14(18) . . . . ? C10 C5 C6 C1 178.17(12) . . . . ? C4 C5 C6 C7 171.01(12) . . . . ? C10 C5 C6 C7 -5.68(19) . . . . ? C1 C6 C7 C8 171.89(13) . . . . ? C5 C6 C7 C8 -4.2(2) . . . . ? C6 C7 C8 C9 6.0(2) . . . . ? C7 C8 C9 C10 2.4(2) . . . . ? C7 C8 C9 S1 -178.11(11) . . . . ? C8 C9 C10 C5 -12.1(2) . . . . ? S1 C9 C10 C5 168.35(9) . . . . ? C8 C9 C10 C11 171.86(12) . . . . ? S1 C9 C10 C11 -7.72(14) . . . . ? C4 C5 C10 C9 -163.22(12) . . . . ? C6 C5 C10 C9 13.26(18) . . . . ? C4 C5 C10 C11 11.9(2) . . . . ? C6 C5 C10 C11 -171.61(13) . . . . ? C9 C10 C11 C12 11.52(16) . . . . ? C5 C10 C11 C12 -163.83(13) . . . . ? C9 C10 C11 C16 -166.87(13) . . . . ? C5 C10 C11 C16 17.8(2) . . . . ? C16 C11 C12 C13 -13.81(19) . . . . ? C10 C11 C12 C13 167.54(12) . . . . ? C16 C11 C12 S1 168.21(9) . . . . ? C10 C11 C12 S1 -10.44(14) . . . . ? C11 C12 C13 C14 -1.8(2) . . . . ? S1 C12 C13 C14 175.93(10) . . . . ? C12 C13 C14 C15 8.8(2) . . . . ? C13 C14 C15 C20 179.34(13) . . . . ? C13 C14 C15 C16 0.3(2) . . . . ? C20 C15 C16 C17 -15.31(18) . . . . ? C14 C15 C16 C17 163.72(12) . . . . ? C20 C15 C16 C11 165.15(12) . . . . ? C14 C15 C16 C11 -15.82(18) . . . . ? C12 C11 C16 C15 21.92(17) . . . . ? C10 C11 C16 C15 -159.77(13) . . . . ? C12 C11 C16 C17 -157.57(13) . . . . ? C10 C11 C16 C17 20.7(2) . . . . ? C15 C16 C17 C18 21.04(18) . . . . ? C11 C16 C17 C18 -159.47(13) . . . . ? C15 C16 C17 C21 -161.48(14) . . . . ? C11 C16 C17 C21 18.0(2) . . . . ? C16 C17 C18 C19 -13.5(2) . . . . ? C21 C17 C18 C19 168.46(13) . . . . ? C16 C17 C18 S2 168.58(10) . . . . ? C21 C17 C18 S2 -9.41(14) . . . . ? C17 C18 C19 C20 -1.2(2) . . . . ? S2 C18 C19 C20 176.45(11) . . . . ? C18 C19 C20 C15 7.8(2) . . . . ? C14 C15 C20 C19 -178.42(13) . . . . ? C16 C15 C20 C19 0.6(2) . . . . ? C18 C17 C21 C22 10.67(16) . . . . ? C16 C17 C21 C22 -166.92(14) . . . . ? C18 C17 C21 C26 -166.34(14) . . . . ? C16 C17 C21 C26 16.1(2) . . . . ? C26 C21 C22 C23 -11.5(2) . . . . ? C17 C21 C22 C23 170.99(13) . . . . ? C26 C21 C22 S2 170.01(10) . . . . ? C17 C21 C22 S2 -7.47(15) . . . . ? C21 C22 C23 C24 0.3(2) . . . . ? S2 C22 C23 C24 178.54(12) . . . . ? C22 C23 C24 C25 6.4(2) . . . . ? C23 C24 C25 C30 175.96(14) . . . . ? C23 C24 C25 C26 -1.4(2) . . . . ? C30 C25 C26 C27 -9.75(19) . . . . ? C24 C25 C26 C27 167.61(13) . . . . ? C30 C25 C26 C21 172.63(12) . . . . ? C24 C25 C26 C21 -10.01(19) . . . . ? C22 C21 C26 C27 -161.50(13) . . . . ? C17 C21 C26 C27 15.4(2) . . . . ? C22 C21 C26 C25 15.96(18) . . . . ? C17 C21 C26 C25 -167.18(13) . . . . ? C25 C26 C27 C28 7.14(19) . . . . ? C21 C26 C27 C28 -175.40(13) . . . . ? C26 C27 C28 C29 0.3(2) . . . . ? C27 C28 C29 C30 -5.2(2) . . . . ? C28 C29 C30 C25 2.4(2) . . . . ? C24 C25 C30 C29 -172.22(14) . . . . ? C26 C25 C30 C29 5.1(2) . . . . ? C10 C9 S1 C12 1.58(11) . . . . ? C8 C9 S1 C12 -178.00(12) . . . . ? C11 C12 S1 C9 5.27(11) . . . . ? C13 C12 S1 C9 -172.69(12) . . . . ? C17 C18 S2 C22 4.51(11) . . . . ? C19 C18 S2 C22 -173.36(12) . . . . ? C21 C22 S2 C18 1.87(11) . . . . ? C23 C22 S2 C18 -176.57(13) . . . . ? _refine_diff_density_max 0.234 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.060 _shelx_res_file ; 9931yng_a.res created by SHELXL-2014/7 TITL 9931yng_a.res in P2(1)/n REM Yadorkari-X generated CELL 1.54187 9.3380 13.6220 16.2990 90.0000 102.2040 90.0000 ZERR 4.0 0.0030 0.0030 0.0040 0.0000 0.0070 0.0000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z REM SPGR P21/n monoclinic SFAC C H S UNIT 120 64 8 SIZE 0.28 0.22 0.15 TEMP -180.0 L.S. 10 FMAP 2 PLAN -20 ACTA CONF HTAB LIST 4 BOND $H MERG 2 OMIT 0 4 0 OMIT 1 3 2 OMIT -1 0 3 WGHT 0.038700 1.306600 FVAR 0.62822 C1 1 0.245875 0.319482 0.120029 11.00000 0.02651 0.01213 = 0.01032 0.00040 -0.00020 -0.00348 AFIX 43 H1 2 0.177669 0.288051 0.076436 11.00000 -1.20000 AFIX 0 C2 1 0.392122 0.314660 0.120139 11.00000 0.02889 0.01269 = 0.01311 -0.00136 0.00666 0.00023 AFIX 43 H2 2 0.424767 0.280634 0.076612 11.00000 -1.20000 AFIX 0 C3 1 0.494103 0.360096 0.184717 11.00000 0.02094 0.01356 = 0.01606 0.00126 0.00593 0.00170 AFIX 43 H3 2 0.595904 0.354988 0.185673 11.00000 -1.20000 AFIX 0 C4 1 0.447357 0.411873 0.246486 11.00000 0.01687 0.00963 = 0.01089 0.00126 0.00031 -0.00025 AFIX 43 H4 2 0.517621 0.441854 0.289943 11.00000 -1.20000 AFIX 0 C5 1 0.296572 0.421371 0.246578 11.00000 0.01697 0.00882 = 0.00875 0.00277 0.00098 -0.00044 C6 1 0.194254 0.370436 0.183662 11.00000 0.01980 0.00970 = 0.01115 0.00288 -0.00019 -0.00131 C7 1 0.043491 0.365756 0.187642 11.00000 0.01842 0.01355 = 0.01475 0.00195 -0.00380 -0.00396 AFIX 43 H7 2 -0.024429 0.335367 0.143283 11.00000 -1.20000 AFIX 0 C8 1 -0.004720 0.404073 0.253888 11.00000 0.01336 0.01793 = 0.01814 0.00399 -0.00054 -0.00269 AFIX 43 H8 2 -0.103400 0.395443 0.259019 11.00000 -1.20000 AFIX 0 C9 1 0.095592 0.457030 0.314885 11.00000 0.01492 0.01435 = 0.01259 0.00321 0.00183 0.00099 C10 1 0.240526 0.475067 0.309134 11.00000 0.01354 0.01131 = 0.00927 0.00310 -0.00065 0.00106 C11 1 0.311838 0.542721 0.374083 11.00000 0.01414 0.01116 = 0.00859 0.00249 0.00028 0.00313 C12 1 0.226780 0.556637 0.434421 11.00000 0.01514 0.01309 = 0.01177 0.00353 0.00204 0.00253 C13 1 0.280133 0.602953 0.512220 11.00000 0.02284 0.01541 = 0.00948 0.00239 0.00499 0.00452 AFIX 43 H13 2 0.218811 0.612953 0.551142 11.00000 -1.20000 AFIX 0 C14 1 0.422172 0.632820 0.529695 11.00000 0.02518 0.01208 = 0.00775 0.00079 -0.00075 0.00274 AFIX 43 H14 2 0.464364 0.655724 0.584530 11.00000 -1.20000 AFIX 0 C15 1 0.509192 0.630625 0.467901 11.00000 0.01783 0.00897 = 0.01065 0.00054 -0.00158 0.00285 C16 1 0.447324 0.596773 0.384787 11.00000 0.01347 0.00961 = 0.01042 0.00019 -0.00002 0.00311 C17 1 0.526001 0.620794 0.320572 11.00000 0.01337 0.00943 = 0.01243 -0.00098 0.00043 0.00164 C18 1 0.675226 0.644146 0.346999 11.00000 0.01439 0.01260 = 0.01633 -0.00055 0.00194 0.00066 C19 1 0.742124 0.664763 0.431020 11.00000 0.01335 0.01387 = 0.01864 -0.00169 -0.00364 0.00004 AFIX 43 H19 2 0.843815 0.679069 0.446753 11.00000 -1.20000 AFIX 0 C20 1 0.656654 0.663540 0.488804 11.00000 0.01971 0.01134 = 0.01185 -0.00088 -0.00467 0.00219 AFIX 43 H20 2 0.696332 0.685156 0.544376 11.00000 -1.20000 AFIX 0 C21 1 0.482183 0.622831 0.229234 11.00000 0.01583 0.00970 = 0.01205 -0.00111 0.00329 -0.00060 C22 1 0.604114 0.629819 0.192513 11.00000 0.01596 0.01541 = 0.01634 -0.00063 0.00426 -0.00116 C23 1 0.595540 0.619599 0.105461 11.00000 0.02216 0.02309 = 0.01713 -0.00058 0.01016 -0.00126 AFIX 43 H23 2 0.680900 0.624538 0.082702 11.00000 -1.20000 AFIX 0 C24 1 0.462241 0.602515 0.054914 11.00000 0.02859 0.01866 = 0.01122 -0.00044 0.00693 -0.00012 AFIX 43 H24 2 0.455887 0.588829 -0.002897 11.00000 -1.20000 AFIX 0 C25 1 0.332076 0.604801 0.087194 11.00000 0.02141 0.01076 = 0.01216 0.00096 0.00199 -0.00075 C26 1 0.339915 0.623082 0.174040 11.00000 0.01672 0.00818 = 0.01154 0.00128 0.00152 -0.00140 C27 1 0.207949 0.644041 0.199996 11.00000 0.01755 0.01113 = 0.01121 0.00214 0.00204 0.00048 AFIX 43 H27 2 0.211202 0.663820 0.256253 11.00000 -1.20000 AFIX 0 C28 1 0.074963 0.636140 0.144790 11.00000 0.01644 0.01557 = 0.01678 0.00447 0.00128 0.00079 AFIX 43 H28 2 -0.012513 0.650848 0.163295 11.00000 -1.20000 AFIX 0 C29 1 0.066888 0.606598 0.061402 11.00000 0.02007 0.01665 = 0.01544 0.00393 -0.00505 -0.00175 AFIX 43 H29 2 -0.025590 0.596065 0.024942 11.00000 -1.20000 AFIX 0 C30 1 0.193289 0.593131 0.033154 11.00000 0.02793 0.01463 = 0.00922 0.00079 -0.00066 -0.00170 AFIX 43 H30 2 0.187756 0.575606 -0.023846 11.00000 -1.20000 AFIX 0 S1 3 0.052368 0.507201 0.404156 11.00000 0.01407 0.02161 = 0.01290 0.00152 0.00416 0.00034 S2 3 0.766274 0.649066 0.264931 11.00000 0.01317 0.02583 = 0.01872 -0.00295 0.00431 -0.00336 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 9931yng_a.res in P2(1)/n REM R1 = 0.0311 for 3666 Fo > 4sig(Fo) and 0.0318 for all 3750 data REM 289 parameters refined using 0 restraints END WGHT 0.0387 1.3057 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.234, deepest hole -0.384, 1-sigma level 0.060 Q1 1 0.2810 0.5429 0.4119 11.00000 0.05 0.23 Q2 1 0.7257 0.6518 0.3124 11.00000 0.05 0.22 Q3 1 0.2772 0.4456 0.2824 11.00000 0.05 0.22 Q4 1 0.3393 0.6153 0.1296 11.00000 0.05 0.21 Q5 1 0.4096 0.6165 0.2013 11.00000 0.05 0.20 Q6 1 0.0548 0.4150 0.2939 11.00000 0.05 0.20 Q7 1 0.2388 0.4027 0.2116 11.00000 0.05 0.19 Q8 1 0.4815 0.6077 0.3509 11.00000 0.05 0.19 Q9 1 0.7151 0.6395 0.3918 11.00000 0.05 0.19 Q10 1 0.2222 0.3430 0.1606 11.00000 0.05 0.18 Q11 1 0.4752 0.6169 0.4274 11.00000 0.05 0.18 Q12 1 0.2808 0.5124 0.3363 11.00000 0.05 0.18 Q13 1 0.4890 0.6201 0.2734 11.00000 0.05 0.18 Q14 1 0.1211 0.3714 0.1859 11.00000 0.05 0.17 Q15 1 0.3699 0.4374 0.2331 11.00000 0.05 0.17 Q16 1 0.6228 0.5142 0.1952 11.00000 0.05 0.17 Q17 1 0.0124 0.4078 0.2086 11.00000 0.05 0.17 Q18 1 0.4656 0.6223 0.5027 11.00000 0.05 0.17 Q19 1 0.3618 0.5798 0.3685 11.00000 0.05 0.17 Q20 1 0.0752 0.4797 0.3502 11.00000 0.05 0.17 ; _shelx_res_checksum 17413 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_201029yanagi _audit_block_doi 10.5517/ccdc.csd.cc26qjm3 _database_code_depnum_ccdc_archive 'CCDC 2047445' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1SC00044F 2021 loop_ _audit_author_name _audit_author_address 'Tomoyuki Yanagi' ;Kyoto university Japan ; _audit_update_record ; 2020-12-01 deposited with the CCDC. 2021-02-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H32, C H2 Cl2' _chemical_formula_sum 'C57 H34 Cl2' _chemical_formula_weight 789.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.57192(4) _cell_length_b 20.53361(10) _cell_length_c 22.43166(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3948.25(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 42861 _cell_measurement_theta_min 2.1650 _cell_measurement_theta_max 72.7300 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_F_000 1640 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 1.786 _shelx_estimated_absorpt_T_min 0.574 _shelx_estimated_absorpt_T_max 0.842 _exptl_absorpt_correction_T_min 0.56640 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 54189 _diffrn_reflns_av_unetI/netI 0.0206 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.918 _diffrn_reflns_theta_max 72.920 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 7819 _reflns_number_gt 7638 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.775 _reflns_Friedel_fraction_max 0.988 _reflns_Friedel_fraction_full 0.999 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+1.8688P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 3267 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.001(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 7819 _refine_ls_number_parameters 532 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0520(3) 0.18758(12) 0.71184(10) 0.0174(5) Uani 1 1 d . . . . . C2 C -0.0461(3) 0.22986(13) 0.67900(11) 0.0192(5) Uani 1 1 d . . . . . H1 H -0.0339 0.2756 0.6833 0.023 Uiso 1 1 calc R U . . . C3 C -0.1587(3) 0.20620(13) 0.64107(11) 0.0229(5) Uani 1 1 d . . . . . H2 H -0.2233 0.2356 0.6196 0.027 Uiso 1 1 calc R U . . . C4 C -0.1783(3) 0.13862(14) 0.63398(11) 0.0245(5) Uani 1 1 d . . . . . H3 H -0.2522 0.1224 0.6061 0.029 Uiso 1 1 calc R U . . . C5 C -0.0912(3) 0.09621(14) 0.66718(11) 0.0230(5) Uani 1 1 d . . . . . H4 H -0.1069 0.0507 0.6626 0.028 Uiso 1 1 calc R U . . . C6 C 0.0225(3) 0.11898(13) 0.70833(11) 0.0201(5) Uani 1 1 d . . . . . C7 C 0.0981(3) 0.07566(12) 0.74870(11) 0.0211(5) Uani 1 1 d . . . . . H5 H 0.0827 0.0300 0.7448 0.025 Uiso 1 1 calc R U . . . C8 C 0.1928(3) 0.09906(12) 0.79299(11) 0.0208(5) Uani 1 1 d . . . . . H6 H 0.2346 0.0704 0.8222 0.025 Uiso 1 1 calc R U . . . C9 C 0.2274(3) 0.16597(12) 0.79469(11) 0.0182(5) Uani 1 1 d . . . . . C10 C 0.1711(3) 0.20886(11) 0.75180(10) 0.0167(5) Uani 1 1 d . . . . . C11 C 0.2485(3) 0.27281(12) 0.76114(10) 0.0171(5) Uani 1 1 d . . . . . C12 C 0.3245(3) 0.26980(12) 0.81606(10) 0.0183(5) Uani 1 1 d . . . . . C13 C 0.3908(3) 0.32507(12) 0.84293(11) 0.0209(5) Uani 1 1 d . . . . . H7 H 0.4443 0.3215 0.8799 0.025 Uiso 1 1 calc R U . . . C14 C 0.3772(3) 0.38404(13) 0.81500(11) 0.0216(5) Uani 1 1 d . . . . . H8 H 0.4134 0.4222 0.8345 0.026 Uiso 1 1 calc R U . . . C15 C 0.3097(3) 0.38907(12) 0.75710(11) 0.0206(5) Uani 1 1 d . . . . . C16 C 0.2595(3) 0.33128(12) 0.72636(11) 0.0180(5) Uani 1 1 d . . . . . C17 C 0.2223(3) 0.33936(12) 0.66433(11) 0.0171(5) Uani 1 1 d . . . . . C18 C 0.1894(3) 0.40162(12) 0.64296(11) 0.0191(5) Uani 1 1 d . . . . . C19 C 0.2218(3) 0.45816(12) 0.67556(11) 0.0221(5) Uani 1 1 d . . . . . H9 H 0.1966 0.4999 0.6601 0.027 Uiso 1 1 calc R U . . . C20 C 0.2913(3) 0.45166(12) 0.73074(11) 0.0225(5) Uani 1 1 d . . . . . H10 H 0.3271 0.4892 0.7513 0.027 Uiso 1 1 calc R U . . . C21 C 0.2562(3) 0.22816(12) 0.60523(10) 0.0164(5) Uani 1 1 d . . . . . C22 C 0.3643(3) 0.19579(12) 0.64316(11) 0.0186(5) Uani 1 1 d . . . . . H11 H 0.4119 0.2190 0.6750 0.022 Uiso 1 1 calc R U . . . C23 C 0.4007(3) 0.13127(12) 0.63429(11) 0.0196(5) Uani 1 1 d . . . . . H12 H 0.4714 0.1101 0.6605 0.024 Uiso 1 1 calc R U . . . C24 C 0.3338(3) 0.09639(12) 0.58658(11) 0.0208(5) Uani 1 1 d . . . . . H13 H 0.3556 0.0513 0.5819 0.025 Uiso 1 1 calc R U . . . C25 C 0.2373(3) 0.12741(12) 0.54697(11) 0.0204(5) Uani 1 1 d . . . . . H14 H 0.1953 0.1038 0.5143 0.024 Uiso 1 1 calc R U . . . C26 C 0.1991(3) 0.19419(12) 0.55398(11) 0.0180(5) Uani 1 1 d . . . . . C27 C 0.1098(3) 0.22819(13) 0.51053(11) 0.0208(5) Uani 1 1 d . . . . . H15 H 0.0694 0.2051 0.4772 0.025 Uiso 1 1 calc R U . . . C28 C 0.0810(3) 0.29354(13) 0.51567(11) 0.0193(5) Uani 1 1 d . . . . . H16 H 0.0291 0.3165 0.4847 0.023 Uiso 1 1 calc R U . . . C29 C 0.1296(3) 0.32599(12) 0.56770(11) 0.0181(5) Uani 1 1 d . . . . . C30 C 0.2050(3) 0.29353(12) 0.61378(11) 0.0173(5) Uani 1 1 d . . . . . C31 C 0.3258(3) 0.20100(12) 0.84036(10) 0.0181(5) Uani 1 1 d . . . . . C32 C 0.2648(3) 0.19554(11) 0.90433(11) 0.0173(5) Uani 1 1 d . . . . . C33 C 0.1180(3) 0.21013(12) 0.92601(12) 0.0213(5) Uani 1 1 d . . . . . H17 H 0.0384 0.2256 0.9002 0.026 Uiso 1 1 calc R U . . . C34 C 0.0893(3) 0.20157(13) 0.98686(12) 0.0236(5) Uani 1 1 d . . . . . H18 H -0.0117 0.2102 1.0024 0.028 Uiso 1 1 calc R U . . . C35 C 0.2075(3) 0.18053(12) 1.02494(11) 0.0227(5) Uani 1 1 d . . . . . H19 H 0.1868 0.1762 1.0664 0.027 Uiso 1 1 calc R U . . . C36 C 0.3556(3) 0.16566(12) 1.00316(11) 0.0207(5) Uani 1 1 d . . . . . H20 H 0.4357 0.1508 1.0291 0.025 Uiso 1 1 calc R U . . . C37 C 0.3832(3) 0.17309(11) 0.94241(11) 0.0173(5) Uani 1 1 d . . . . . C38 C 0.5235(3) 0.16094(12) 0.90712(11) 0.0179(5) Uani 1 1 d . . . . . C39 C 0.6697(3) 0.13767(12) 0.92424(12) 0.0216(5) Uani 1 1 d . . . . . H21 H 0.6914 0.1280 0.9648 0.026 Uiso 1 1 calc R U . . . C40 C 0.7828(3) 0.12900(13) 0.88050(13) 0.0256(6) Uani 1 1 d . . . . . H22 H 0.8831 0.1132 0.8913 0.031 Uiso 1 1 calc R U . . . C41 C 0.7506(3) 0.14328(14) 0.82120(13) 0.0277(6) Uani 1 1 d . . . . . H23 H 0.8292 0.1368 0.7919 0.033 Uiso 1 1 calc R U . . . C42 C 0.6050(3) 0.16700(13) 0.80388(12) 0.0243(5) Uani 1 1 d . . . . . H24 H 0.5838 0.1770 0.7633 0.029 Uiso 1 1 calc R U . . . C43 C 0.4919(3) 0.17563(12) 0.84747(11) 0.0185(5) Uani 1 1 d . . . . . C44 C 0.1135(3) 0.39805(12) 0.58192(11) 0.0184(5) Uani 1 1 d . . . . . C45 C 0.1840(3) 0.44294(12) 0.53509(11) 0.0190(5) Uani 1 1 d . . . . . C46 C 0.3325(3) 0.44103(12) 0.51127(11) 0.0219(5) Uani 1 1 d . . . . . H25 H 0.4055 0.4091 0.5240 0.026 Uiso 1 1 calc R U . . . C47 C 0.3731(3) 0.48698(13) 0.46813(12) 0.0248(5) Uani 1 1 d . . . . . H26 H 0.4750 0.4867 0.4515 0.030 Uiso 1 1 calc R U . . . C48 C 0.2651(3) 0.53331(13) 0.44925(12) 0.0253(6) Uani 1 1 d . . . . . H27 H 0.2941 0.5639 0.4195 0.030 Uiso 1 1 calc R U . . . C49 C 0.1155(3) 0.53547(12) 0.47323(12) 0.0238(5) Uani 1 1 d . . . . . H28 H 0.0423 0.5672 0.4602 0.029 Uiso 1 1 calc R U . . . C50 C 0.0755(3) 0.48996(12) 0.51685(11) 0.0204(5) Uani 1 1 d . . . . . C51 C -0.0707(3) 0.47943(12) 0.54946(11) 0.0207(5) Uani 1 1 d . . . . . C52 C -0.2114(3) 0.51327(13) 0.54845(12) 0.0241(5) Uani 1 1 d . . . . . H29 H -0.2236 0.5506 0.5238 0.029 Uiso 1 1 calc R U . . . C53 C -0.3335(3) 0.49183(13) 0.58391(13) 0.0263(6) Uani 1 1 d . . . . . H30 H -0.4293 0.5151 0.5840 0.032 Uiso 1 1 calc R U . . . C54 C -0.3175(3) 0.43632(13) 0.61952(12) 0.0257(5) Uani 1 1 d . . . . . H31 H -0.4030 0.4217 0.6429 0.031 Uiso 1 1 calc R U . . . C55 C -0.1767(3) 0.40228(13) 0.62091(11) 0.0237(5) Uani 1 1 d . . . . . H32 H -0.1650 0.3647 0.6453 0.028 Uiso 1 1 calc R U . . . C56 C -0.0540(3) 0.42450(12) 0.58590(11) 0.0192(5) Uani 1 1 d . . . . . Cl1 Cl 0.84055(14) 0.43955(4) 0.85756(4) 0.0533(3) Uani 1 1 d . U . . . Cl2 Cl 0.82167(12) 0.30824(4) 0.80912(4) 0.0519(2) Uani 1 1 d . U . . . C58 C 0.9317(11) 0.3783(4) 0.8111(4) 0.049(3) Uiso 0.512(16) 1 d . . P A 1 H33 H 0.9439 0.3955 0.7701 0.059 Uiso 0.512(16) 1 calc R U P A 1 H34 H 1.0368 0.3682 0.8269 0.059 Uiso 0.512(16) 1 calc R U P A 1 C59 C 0.8560(11) 0.3918(4) 0.7926(4) 0.045(3) Uiso 0.488(16) 1 d . . P A 2 H35 H 0.9615 0.3969 0.7753 0.054 Uiso 0.488(16) 1 calc R U P A 2 H36 H 0.7791 0.4069 0.7627 0.054 Uiso 0.488(16) 1 calc R U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0191(11) 0.0206(12) 0.0126(10) -0.0007(9) 0.0032(9) 0.0012(9) C2 0.0177(11) 0.0227(12) 0.0173(11) -0.0011(10) 0.0024(9) 0.0026(10) C3 0.0185(11) 0.0295(13) 0.0207(12) -0.0005(10) 0.0006(10) 0.0024(10) C4 0.0198(12) 0.0332(14) 0.0205(12) -0.0059(10) -0.0004(10) -0.0024(11) C5 0.0226(12) 0.0254(13) 0.0211(12) -0.0048(10) 0.0039(10) -0.0040(10) C6 0.0210(12) 0.0225(12) 0.0167(11) -0.0028(9) 0.0038(10) -0.0013(10) C7 0.0248(12) 0.0182(12) 0.0204(12) -0.0021(9) 0.0030(10) 0.0004(10) C8 0.0248(12) 0.0198(11) 0.0179(11) 0.0010(9) 0.0017(10) 0.0025(10) C9 0.0189(11) 0.0203(11) 0.0155(11) -0.0011(9) 0.0008(9) 0.0021(9) C10 0.0183(10) 0.0178(11) 0.0140(10) -0.0014(9) 0.0027(9) 0.0016(9) C11 0.0171(10) 0.0191(11) 0.0150(11) -0.0022(9) -0.0008(9) 0.0028(9) C12 0.0201(11) 0.0194(11) 0.0152(11) 0.0009(9) -0.0010(9) 0.0020(10) C13 0.0229(12) 0.0240(12) 0.0158(11) -0.0028(10) -0.0040(9) 0.0007(10) C14 0.0270(13) 0.0204(12) 0.0174(11) -0.0035(9) -0.0035(10) -0.0020(10) C15 0.0224(12) 0.0205(12) 0.0188(12) -0.0016(9) -0.0014(10) 0.0007(10) C16 0.0186(11) 0.0179(11) 0.0175(11) -0.0009(9) -0.0001(9) 0.0025(9) C17 0.0172(11) 0.0174(11) 0.0167(11) -0.0004(9) -0.0001(9) 0.0010(9) C18 0.0213(11) 0.0193(11) 0.0169(11) 0.0003(9) 0.0002(10) 0.0014(10) C19 0.0285(13) 0.0168(11) 0.0211(12) 0.0013(9) -0.0027(10) 0.0023(10) C20 0.0302(14) 0.0177(11) 0.0197(12) -0.0035(10) -0.0008(10) -0.0003(10) C21 0.0162(10) 0.0177(11) 0.0152(11) 0.0008(9) 0.0030(9) -0.0003(9) C22 0.0184(11) 0.0215(12) 0.0159(11) 0.0005(9) 0.0009(9) 0.0005(9) C23 0.0202(11) 0.0201(12) 0.0187(12) 0.0025(9) 0.0026(9) 0.0035(10) C24 0.0225(12) 0.0159(11) 0.0240(12) -0.0003(9) 0.0051(10) 0.0023(10) C25 0.0225(12) 0.0194(12) 0.0192(12) -0.0026(9) 0.0041(10) -0.0025(10) C26 0.0175(11) 0.0183(11) 0.0181(11) -0.0001(9) 0.0029(9) -0.0017(9) C27 0.0204(11) 0.0240(12) 0.0178(11) -0.0009(10) -0.0013(10) -0.0017(10) C28 0.0193(11) 0.0230(12) 0.0155(11) 0.0012(9) -0.0017(9) 0.0011(9) C29 0.0181(11) 0.0187(11) 0.0175(11) 0.0014(9) 0.0002(9) 0.0005(9) C30 0.0178(11) 0.0189(12) 0.0152(11) 0.0012(9) 0.0002(9) -0.0001(9) C31 0.0206(11) 0.0188(11) 0.0147(11) -0.0005(9) -0.0010(9) 0.0013(9) C32 0.0212(11) 0.0151(10) 0.0155(11) -0.0004(9) 0.0006(9) 0.0000(9) C33 0.0212(11) 0.0195(12) 0.0231(12) -0.0019(10) 0.0002(10) 0.0014(10) C34 0.0263(13) 0.0202(12) 0.0242(13) -0.0016(10) 0.0078(10) 0.0021(10) C35 0.0316(14) 0.0208(12) 0.0157(11) -0.0026(9) 0.0045(10) -0.0028(10) C36 0.0257(12) 0.0211(12) 0.0154(11) 0.0012(9) -0.0020(9) -0.0047(10) C37 0.0196(11) 0.0143(11) 0.0180(11) -0.0002(9) -0.0005(9) -0.0025(9) C38 0.0205(12) 0.0155(11) 0.0176(11) 0.0008(9) -0.0015(9) -0.0011(9) C39 0.0210(12) 0.0196(11) 0.0241(12) 0.0024(10) -0.0037(10) -0.0008(10) C40 0.0182(12) 0.0203(12) 0.0382(15) 0.0012(11) 0.0011(11) 0.0018(10) C41 0.0237(13) 0.0263(13) 0.0331(15) -0.0003(11) 0.0095(11) 0.0014(11) C42 0.0271(13) 0.0264(13) 0.0194(12) 0.0001(10) 0.0046(10) 0.0015(11) C43 0.0205(11) 0.0164(11) 0.0186(11) 0.0011(9) 0.0002(9) 0.0007(9) C44 0.0194(11) 0.0189(12) 0.0170(11) 0.0008(9) -0.0017(9) 0.0017(9) C45 0.0254(12) 0.0157(11) 0.0160(11) -0.0016(9) -0.0056(10) -0.0008(10) C46 0.0256(12) 0.0206(12) 0.0195(12) -0.0004(9) -0.0024(10) 0.0020(10) C47 0.0304(14) 0.0252(13) 0.0189(12) -0.0015(10) -0.0012(10) -0.0023(11) C48 0.0375(15) 0.0200(12) 0.0183(12) 0.0016(10) -0.0053(11) -0.0063(11) C49 0.0339(14) 0.0170(11) 0.0206(12) 0.0005(10) -0.0108(11) 0.0002(11) C50 0.0274(13) 0.0158(11) 0.0179(11) -0.0036(9) -0.0071(10) 0.0010(10) C51 0.0262(13) 0.0161(12) 0.0197(12) -0.0029(10) -0.0076(10) 0.0020(9) C52 0.0280(14) 0.0180(11) 0.0262(13) -0.0049(10) -0.0097(11) 0.0043(10) C53 0.0232(12) 0.0242(13) 0.0315(14) -0.0085(11) -0.0075(11) 0.0068(11) C54 0.0233(13) 0.0272(13) 0.0267(13) -0.0057(10) -0.0026(11) 0.0029(11) C55 0.0251(12) 0.0239(12) 0.0221(12) -0.0007(10) -0.0011(10) 0.0046(11) C56 0.0217(12) 0.0181(12) 0.0178(12) -0.0047(9) -0.0046(10) 0.0028(9) Cl1 0.0917(7) 0.0342(4) 0.0340(4) -0.0033(3) 0.0037(4) -0.0187(5) Cl2 0.0618(5) 0.0387(4) 0.0552(5) -0.0144(4) 0.0223(4) -0.0056(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.415(3) . ? C1 C10 1.427(3) . ? C1 C6 1.433(3) . ? C2 C3 1.375(4) . ? C2 H1 0.9500 . ? C3 C4 1.407(4) . ? C3 H2 0.9500 . ? C4 C5 1.368(4) . ? C4 H3 0.9500 . ? C5 C6 1.421(4) . ? C5 H4 0.9500 . ? C6 C7 1.425(4) . ? C7 C8 1.370(4) . ? C7 H5 0.9500 . ? C8 C9 1.406(3) . ? C8 H6 0.9500 . ? C9 C10 1.391(3) . ? C9 C31 1.509(3) . ? C10 C11 1.486(3) . ? C11 C12 1.395(3) . ? C11 C16 1.435(3) . ? C12 C13 1.405(3) . ? C12 C31 1.514(3) . ? C13 C14 1.368(4) . ? C13 H7 0.9500 . ? C14 C15 1.426(3) . ? C14 H8 0.9500 . ? C15 C20 1.424(4) . ? C15 C16 1.438(3) . ? C16 C17 1.437(3) . ? C17 C18 1.394(3) . ? C17 C30 1.481(3) . ? C18 C19 1.400(4) . ? C18 C44 1.518(3) . ? C19 C20 1.380(4) . ? C19 H9 0.9500 . ? C20 H10 0.9500 . ? C21 C22 1.423(3) . ? C21 C30 1.425(3) . ? C21 C26 1.431(3) . ? C22 C23 1.375(4) . ? C22 H11 0.9500 . ? C23 C24 1.410(4) . ? C23 H12 0.9500 . ? C24 C25 1.371(4) . ? C24 H13 0.9500 . ? C25 C26 1.419(3) . ? C25 H14 0.9500 . ? C26 C27 1.422(3) . ? C27 C28 1.369(4) . ? C27 H15 0.9500 . ? C28 C29 1.407(3) . ? C28 H16 0.9500 . ? C29 C30 1.390(3) . ? C29 C44 1.520(3) . ? C31 C43 1.525(3) . ? C31 C32 1.531(3) . ? C32 C33 1.383(3) . ? C32 C37 1.404(3) . ? C33 C34 1.398(4) . ? C33 H17 0.9500 . ? C34 C35 1.394(4) . ? C34 H18 0.9500 . ? C35 C36 1.395(4) . ? C35 H19 0.9500 . ? C36 C37 1.391(3) . ? C36 H20 0.9500 . ? C37 C38 1.461(3) . ? C38 C39 1.395(3) . ? C38 C43 1.398(3) . ? C39 C40 1.391(4) . ? C39 H21 0.9500 . ? C40 C41 1.390(4) . ? C40 H22 0.9500 . ? C41 C42 1.395(4) . ? C41 H23 0.9500 . ? C42 C43 1.388(3) . ? C42 H24 0.9500 . ? C44 C45 1.522(3) . ? C44 C56 1.538(3) . ? C45 C46 1.382(4) . ? C45 C50 1.401(4) . ? C46 C47 1.395(4) . ? C46 H25 0.9500 . ? C47 C48 1.393(4) . ? C47 H26 0.9500 . ? C48 C49 1.391(4) . ? C48 H27 0.9500 . ? C49 C50 1.396(4) . ? C49 H28 0.9500 . ? C50 C51 1.468(4) . ? C51 C52 1.392(4) . ? C51 C56 1.400(4) . ? C52 C53 1.386(4) . ? C52 H29 0.9500 . ? C53 C54 1.399(4) . ? C53 H30 0.9500 . ? C54 C55 1.395(4) . ? C54 H31 0.9500 . ? C55 C56 1.390(4) . ? C55 H32 0.9500 . ? Cl1 C59 1.762(8) . ? Cl1 C58 1.810(8) . ? Cl2 C58 1.721(8) . ? Cl2 C59 1.779(8) . ? C58 H33 0.9900 . ? C58 H34 0.9900 . ? C59 H35 0.9900 . ? C59 H36 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 124.3(2) . . ? C2 C1 C6 118.0(2) . . ? C10 C1 C6 117.5(2) . . ? C3 C2 C1 121.5(2) . . ? C3 C2 H1 119.3 . . ? C1 C2 H1 119.3 . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H2 119.9 . . ? C4 C3 H2 119.9 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H3 120.0 . . ? C3 C4 H3 120.0 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H4 119.4 . . ? C6 C5 H4 119.4 . . ? C5 C6 C7 121.3(2) . . ? C5 C6 C1 118.7(2) . . ? C7 C6 C1 119.9(2) . . ? C8 C7 C6 120.8(2) . . ? C8 C7 H5 119.6 . . ? C6 C7 H5 119.6 . . ? C7 C8 C9 119.2(2) . . ? C7 C8 H6 120.4 . . ? C9 C8 H6 120.4 . . ? C10 C9 C8 121.8(2) . . ? C10 C9 C31 111.2(2) . . ? C8 C9 C31 127.0(2) . . ? C9 C10 C1 119.3(2) . . ? C9 C10 C11 107.9(2) . . ? C1 C10 C11 132.7(2) . . ? C12 C11 C16 119.1(2) . . ? C12 C11 C10 107.1(2) . . ? C16 C11 C10 133.8(2) . . ? C11 C12 C13 122.1(2) . . ? C11 C12 C31 111.3(2) . . ? C13 C12 C31 126.6(2) . . ? C14 C13 C12 118.9(2) . . ? C14 C13 H7 120.5 . . ? C12 C13 H7 120.5 . . ? C13 C14 C15 121.1(2) . . ? C13 C14 H8 119.5 . . ? C15 C14 H8 119.5 . . ? C20 C15 C14 119.3(2) . . ? C20 C15 C16 120.8(2) . . ? C14 C15 C16 119.9(2) . . ? C11 C16 C17 127.5(2) . . ? C11 C16 C15 116.7(2) . . ? C17 C16 C15 115.8(2) . . ? C18 C17 C16 118.9(2) . . ? C18 C17 C30 107.4(2) . . ? C16 C17 C30 133.6(2) . . ? C17 C18 C19 122.7(2) . . ? C17 C18 C44 110.6(2) . . ? C19 C18 C44 126.6(2) . . ? C20 C19 C18 118.3(2) . . ? C20 C19 H9 120.9 . . ? C18 C19 H9 120.9 . . ? C19 C20 C15 120.5(2) . . ? C19 C20 H10 119.7 . . ? C15 C20 H10 119.7 . . ? C22 C21 C30 124.0(2) . . ? C22 C21 C26 118.4(2) . . ? C30 C21 C26 117.5(2) . . ? C23 C22 C21 120.7(2) . . ? C23 C22 H11 119.6 . . ? C21 C22 H11 119.6 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H12 119.8 . . ? C24 C23 H12 119.8 . . ? C25 C24 C23 120.1(2) . . ? C25 C24 H13 120.0 . . ? C23 C24 H13 120.0 . . ? C24 C25 C26 121.1(2) . . ? C24 C25 H14 119.4 . . ? C26 C25 H14 119.4 . . ? C25 C26 C27 121.5(2) . . ? C25 C26 C21 118.8(2) . . ? C27 C26 C21 119.7(2) . . ? C28 C27 C26 121.4(2) . . ? C28 C27 H15 119.3 . . ? C26 C27 H15 119.3 . . ? C27 C28 C29 118.7(2) . . ? C27 C28 H16 120.6 . . ? C29 C28 H16 120.6 . . ? C30 C29 C28 121.8(2) . . ? C30 C29 C44 110.7(2) . . ? C28 C29 C44 127.5(2) . . ? C29 C30 C21 119.7(2) . . ? C29 C30 C17 108.1(2) . . ? C21 C30 C17 132.1(2) . . ? C9 C31 C12 101.31(19) . . ? C9 C31 C43 115.5(2) . . ? C12 C31 C43 111.3(2) . . ? C9 C31 C32 114.2(2) . . ? C12 C31 C32 113.77(19) . . ? C43 C31 C32 101.28(19) . . ? C33 C32 C37 121.0(2) . . ? C33 C32 C31 128.6(2) . . ? C37 C32 C31 110.3(2) . . ? C32 C33 C34 118.4(2) . . ? C32 C33 H17 120.8 . . ? C34 C33 H17 120.8 . . ? C35 C34 C33 120.6(2) . . ? C35 C34 H18 119.7 . . ? C33 C34 H18 119.7 . . ? C34 C35 C36 121.0(2) . . ? C34 C35 H19 119.5 . . ? C36 C35 H19 119.5 . . ? C37 C36 C35 118.3(2) . . ? C37 C36 H20 120.9 . . ? C35 C36 H20 120.9 . . ? C36 C37 C32 120.6(2) . . ? C36 C37 C38 130.7(2) . . ? C32 C37 C38 108.7(2) . . ? C39 C38 C43 120.7(2) . . ? C39 C38 C37 130.4(2) . . ? C43 C38 C37 108.8(2) . . ? C40 C39 C38 118.4(2) . . ? C40 C39 H21 120.8 . . ? C38 C39 H21 120.8 . . ? C41 C40 C39 120.6(2) . . ? C41 C40 H22 119.7 . . ? C39 C40 H22 119.7 . . ? C40 C41 C42 121.2(3) . . ? C40 C41 H23 119.4 . . ? C42 C41 H23 119.4 . . ? C43 C42 C41 118.2(2) . . ? C43 C42 H24 120.9 . . ? C41 C42 H24 120.9 . . ? C42 C43 C38 120.8(2) . . ? C42 C43 C31 128.5(2) . . ? C38 C43 C31 110.8(2) . . ? C18 C44 C29 101.39(19) . . ? C18 C44 C45 115.0(2) . . ? C29 C44 C45 114.1(2) . . ? C18 C44 C56 109.3(2) . . ? C29 C44 C56 116.1(2) . . ? C45 C44 C56 101.3(2) . . ? C46 C45 C50 121.2(2) . . ? C46 C45 C44 128.0(2) . . ? C50 C45 C44 110.8(2) . . ? C45 C46 C47 118.6(2) . . ? C45 C46 H25 120.7 . . ? C47 C46 H25 120.7 . . ? C48 C47 C46 120.5(3) . . ? C48 C47 H26 119.8 . . ? C46 C47 H26 119.8 . . ? C49 C48 C47 121.1(3) . . ? C49 C48 H27 119.4 . . ? C47 C48 H27 119.4 . . ? C48 C49 C50 118.4(2) . . ? C48 C49 H28 120.8 . . ? C50 C49 H28 120.8 . . ? C49 C50 C45 120.2(2) . . ? C49 C50 C51 131.1(2) . . ? C45 C50 C51 108.6(2) . . ? C52 C51 C56 120.0(2) . . ? C52 C51 C50 131.2(2) . . ? C56 C51 C50 108.8(2) . . ? C53 C52 C51 119.1(2) . . ? C53 C52 H29 120.5 . . ? C51 C52 H29 120.5 . . ? C52 C53 C54 120.8(2) . . ? C52 C53 H30 119.6 . . ? C54 C53 H30 119.6 . . ? C55 C54 C53 120.4(3) . . ? C55 C54 H31 119.8 . . ? C53 C54 H31 119.8 . . ? C56 C55 C54 118.5(2) . . ? C56 C55 H32 120.7 . . ? C54 C55 H32 120.7 . . ? C55 C56 C51 121.1(2) . . ? C55 C56 C44 128.6(2) . . ? C51 C56 C44 110.2(2) . . ? Cl2 C58 Cl1 111.1(4) . . ? Cl2 C58 H33 109.4 . . ? Cl1 C58 H33 109.4 . . ? Cl2 C58 H34 109.4 . . ? Cl1 C58 H34 109.4 . . ? H33 C58 H34 108.0 . . ? Cl1 C59 Cl2 110.6(4) . . ? Cl1 C59 H35 109.5 . . ? Cl2 C59 H35 109.5 . . ? Cl1 C59 H36 109.5 . . ? Cl2 C59 H36 109.5 . . ? H35 C59 H36 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 179.9(2) . . . . ? C6 C1 C2 C3 -5.1(4) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 3.5(4) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? C4 C5 C6 C7 171.3(2) . . . . ? C4 C5 C6 C1 -4.0(4) . . . . ? C2 C1 C6 C5 7.1(3) . . . . ? C10 C1 C6 C5 -177.5(2) . . . . ? C2 C1 C6 C7 -168.3(2) . . . . ? C10 C1 C6 C7 7.0(3) . . . . ? C5 C6 C7 C8 -171.9(2) . . . . ? C1 C6 C7 C8 3.4(4) . . . . ? C6 C7 C8 C9 -6.3(4) . . . . ? C7 C8 C9 C10 -1.5(4) . . . . ? C7 C8 C9 C31 178.6(2) . . . . ? C8 C9 C10 C1 12.2(4) . . . . ? C31 C9 C10 C1 -167.9(2) . . . . ? C8 C9 C10 C11 -171.3(2) . . . . ? C31 C9 C10 C11 8.6(3) . . . . ? C2 C1 C10 C9 160.5(2) . . . . ? C6 C1 C10 C9 -14.6(3) . . . . ? C2 C1 C10 C11 -14.9(4) . . . . ? C6 C1 C10 C11 170.0(2) . . . . ? C9 C10 C11 C12 -11.5(3) . . . . ? C1 C10 C11 C12 164.2(3) . . . . ? C9 C10 C11 C16 167.5(3) . . . . ? C1 C10 C11 C16 -16.7(5) . . . . ? C16 C11 C12 C13 10.2(4) . . . . ? C10 C11 C12 C13 -170.6(2) . . . . ? C16 C11 C12 C31 -169.1(2) . . . . ? C10 C11 C12 C31 10.1(3) . . . . ? C11 C12 C13 C14 1.6(4) . . . . ? C31 C12 C13 C14 -179.3(2) . . . . ? C12 C13 C14 C15 -5.7(4) . . . . ? C13 C14 C15 C20 177.2(2) . . . . ? C13 C14 C15 C16 -2.1(4) . . . . ? C12 C11 C16 C17 164.4(2) . . . . ? C10 C11 C16 C17 -14.5(4) . . . . ? C12 C11 C16 C15 -17.3(3) . . . . ? C10 C11 C16 C15 163.8(3) . . . . ? C20 C15 C16 C11 -165.8(2) . . . . ? C14 C15 C16 C11 13.4(4) . . . . ? C20 C15 C16 C17 12.7(4) . . . . ? C14 C15 C16 C17 -168.0(2) . . . . ? C11 C16 C17 C18 158.6(2) . . . . ? C15 C16 C17 C18 -19.7(3) . . . . ? C11 C16 C17 C30 -19.3(4) . . . . ? C15 C16 C17 C30 162.3(3) . . . . ? C16 C17 C18 C19 13.6(4) . . . . ? C30 C17 C18 C19 -168.0(2) . . . . ? C16 C17 C18 C44 -165.4(2) . . . . ? C30 C17 C18 C44 13.1(3) . . . . ? C17 C18 C19 C20 1.0(4) . . . . ? C44 C18 C19 C20 179.8(2) . . . . ? C18 C19 C20 C15 -8.5(4) . . . . ? C14 C15 C20 C19 -177.9(3) . . . . ? C16 C15 C20 C19 1.3(4) . . . . ? C30 C21 C22 C23 175.8(2) . . . . ? C26 C21 C22 C23 -6.6(3) . . . . ? C21 C22 C23 C24 1.3(4) . . . . ? C22 C23 C24 C25 3.0(4) . . . . ? C23 C24 C25 C26 -1.9(4) . . . . ? C24 C25 C26 C27 174.7(2) . . . . ? C24 C25 C26 C21 -3.4(4) . . . . ? C22 C21 C26 C25 7.6(3) . . . . ? C30 C21 C26 C25 -174.7(2) . . . . ? C22 C21 C26 C27 -170.6(2) . . . . ? C30 C21 C26 C27 7.1(3) . . . . ? C25 C26 C27 C28 -176.1(2) . . . . ? C21 C26 C27 C28 2.0(4) . . . . ? C26 C27 C28 C29 -5.5(4) . . . . ? C27 C28 C29 C30 -0.3(4) . . . . ? C27 C28 C29 C44 178.2(2) . . . . ? C28 C29 C30 C21 9.6(4) . . . . ? C44 C29 C30 C21 -169.1(2) . . . . ? C28 C29 C30 C17 -173.1(2) . . . . ? C44 C29 C30 C17 8.2(3) . . . . ? C22 C21 C30 C29 164.8(2) . . . . ? C26 C21 C30 C29 -12.8(3) . . . . ? C22 C21 C30 C17 -11.7(4) . . . . ? C26 C21 C30 C17 170.7(2) . . . . ? C18 C17 C30 C29 -13.2(3) . . . . ? C16 C17 C30 C29 164.9(3) . . . . ? C18 C17 C30 C21 163.6(3) . . . . ? C16 C17 C30 C21 -18.2(5) . . . . ? C10 C9 C31 C12 -2.5(3) . . . . ? C8 C9 C31 C12 177.4(2) . . . . ? C10 C9 C31 C43 -122.9(2) . . . . ? C8 C9 C31 C43 57.0(3) . . . . ? C10 C9 C31 C32 120.2(2) . . . . ? C8 C9 C31 C32 -59.9(3) . . . . ? C11 C12 C31 C9 -5.0(3) . . . . ? C13 C12 C31 C9 175.8(2) . . . . ? C11 C12 C31 C43 118.3(2) . . . . ? C13 C12 C31 C43 -60.9(3) . . . . ? C11 C12 C31 C32 -128.0(2) . . . . ? C13 C12 C31 C32 52.7(3) . . . . ? C9 C31 C32 C33 -53.5(3) . . . . ? C12 C31 C32 C33 62.1(3) . . . . ? C43 C31 C32 C33 -178.3(2) . . . . ? C9 C31 C32 C37 127.2(2) . . . . ? C12 C31 C32 C37 -117.1(2) . . . . ? C43 C31 C32 C37 2.5(3) . . . . ? C37 C32 C33 C34 -0.4(4) . . . . ? C31 C32 C33 C34 -179.6(2) . . . . ? C32 C33 C34 C35 1.7(4) . . . . ? C33 C34 C35 C36 -1.9(4) . . . . ? C34 C35 C36 C37 0.7(4) . . . . ? C35 C36 C37 C32 0.5(4) . . . . ? C35 C36 C37 C38 -179.3(2) . . . . ? C33 C32 C37 C36 -0.7(4) . . . . ? C31 C32 C37 C36 178.6(2) . . . . ? C33 C32 C37 C38 179.2(2) . . . . ? C31 C32 C37 C38 -1.6(3) . . . . ? C36 C37 C38 C39 0.8(5) . . . . ? C32 C37 C38 C39 -179.1(2) . . . . ? C36 C37 C38 C43 179.7(3) . . . . ? C32 C37 C38 C43 -0.2(3) . . . . ? C43 C38 C39 C40 -0.5(4) . . . . ? C37 C38 C39 C40 178.3(2) . . . . ? C38 C39 C40 C41 0.1(4) . . . . ? C39 C40 C41 C42 0.4(4) . . . . ? C40 C41 C42 C43 -0.5(4) . . . . ? C41 C42 C43 C38 0.0(4) . . . . ? C41 C42 C43 C31 179.6(2) . . . . ? C39 C38 C43 C42 0.4(4) . . . . ? C37 C38 C43 C42 -178.6(2) . . . . ? C39 C38 C43 C31 -179.2(2) . . . . ? C37 C38 C43 C31 1.8(3) . . . . ? C9 C31 C43 C42 53.9(3) . . . . ? C12 C31 C43 C42 -60.8(3) . . . . ? C32 C31 C43 C42 177.9(3) . . . . ? C9 C31 C43 C38 -126.5(2) . . . . ? C12 C31 C43 C38 118.7(2) . . . . ? C32 C31 C43 C38 -2.6(3) . . . . ? C17 C18 C44 C29 -8.0(3) . . . . ? C19 C18 C44 C29 173.1(2) . . . . ? C17 C18 C44 C45 -131.6(2) . . . . ? C19 C18 C44 C45 49.5(3) . . . . ? C17 C18 C44 C56 115.2(2) . . . . ? C19 C18 C44 C56 -63.7(3) . . . . ? C30 C29 C44 C18 -0.5(3) . . . . ? C28 C29 C44 C18 -179.2(2) . . . . ? C30 C29 C44 C45 123.8(2) . . . . ? C28 C29 C44 C45 -54.9(3) . . . . ? C30 C29 C44 C56 -118.8(2) . . . . ? C28 C29 C44 C56 62.5(3) . . . . ? C18 C44 C45 C46 64.7(3) . . . . ? C29 C44 C45 C46 -51.9(3) . . . . ? C56 C44 C45 C46 -177.5(2) . . . . ? C18 C44 C45 C50 -115.5(2) . . . . ? C29 C44 C45 C50 127.9(2) . . . . ? C56 C44 C45 C50 2.3(3) . . . . ? C50 C45 C46 C47 -0.3(4) . . . . ? C44 C45 C46 C47 179.6(2) . . . . ? C45 C46 C47 C48 -0.6(4) . . . . ? C46 C47 C48 C49 0.7(4) . . . . ? C47 C48 C49 C50 0.0(4) . . . . ? C48 C49 C50 C45 -0.8(4) . . . . ? C48 C49 C50 C51 -179.1(2) . . . . ? C46 C45 C50 C49 1.0(4) . . . . ? C44 C45 C50 C49 -178.9(2) . . . . ? C46 C45 C50 C51 179.7(2) . . . . ? C44 C45 C50 C51 -0.2(3) . . . . ? C49 C50 C51 C52 -3.0(5) . . . . ? C45 C50 C51 C52 178.5(3) . . . . ? C49 C50 C51 C56 176.2(3) . . . . ? C45 C50 C51 C56 -2.3(3) . . . . ? C56 C51 C52 C53 0.1(4) . . . . ? C50 C51 C52 C53 179.1(2) . . . . ? C51 C52 C53 C54 -1.1(4) . . . . ? C52 C53 C54 C55 1.3(4) . . . . ? C53 C54 C55 C56 -0.5(4) . . . . ? C54 C55 C56 C51 -0.6(4) . . . . ? C54 C55 C56 C44 176.6(2) . . . . ? C52 C51 C56 C55 0.8(4) . . . . ? C50 C51 C56 C55 -178.4(2) . . . . ? C52 C51 C56 C44 -176.9(2) . . . . ? C50 C51 C56 C44 3.8(3) . . . . ? C18 C44 C56 C55 -59.4(3) . . . . ? C29 C44 C56 C55 54.5(3) . . . . ? C45 C44 C56 C55 178.8(2) . . . . ? C18 C44 C56 C51 118.1(2) . . . . ? C29 C44 C56 C51 -128.0(2) . . . . ? C45 C44 C56 C51 -3.7(3) . . . . ? _refine_diff_density_max 0.482 _refine_diff_density_min -0.701 _refine_diff_density_rms 0.048 _shelx_res_file ; 201029yanagi.res created by SHELXL-2014/7 TITL 201029yanagi_a.res in P2(1)2(1)2(1) REM Yadorkari-X generated CELL 1.54184 8.5719 20.5336 22.4317 90.0000 90.0000 90.0000 ZERR 4.0 0.0000 0.0001 0.0001 0.0000 0.0000 0.0000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM 1/2+X, 1/2-Y, -Z SYMM -X, 1/2+Y, 1/2-Z REM SPGR P212121 orthorhombic SFAC C H Cl UNIT 228 136 8 SIZE 0.35 0.17 0.10 TEMP -180.0 L.S. 10 FMAP 2 PLAN -20 ACTA CONF HTAB LIST 4 BOND $H ISOR 0.02 C57 Cl1 Cl2 SIMU 0.02 C57 Cl1 Cl2 WGHT 0.058900 1.868800 FVAR 3.39884 0.51200 C1 1 0.052002 0.187578 0.711837 11.00000 0.01908 0.02058 = 0.01265 -0.00067 0.00324 0.00120 C2 1 -0.046068 0.229864 0.679002 11.00000 0.01765 0.02275 = 0.01733 -0.00110 0.00236 0.00260 AFIX 43 H1 2 -0.033855 0.275612 0.683258 11.00000 -1.20000 AFIX 0 C3 1 -0.158656 0.206196 0.641070 11.00000 0.01852 0.02948 = 0.02071 -0.00054 0.00057 0.00238 AFIX 43 H2 2 -0.223303 0.235558 0.619600 11.00000 -1.20000 AFIX 0 C4 1 -0.178334 0.138622 0.633982 11.00000 0.01975 0.03318 = 0.02050 -0.00588 -0.00036 -0.00241 AFIX 43 H3 2 -0.252217 0.122430 0.606111 11.00000 -1.20000 AFIX 0 C5 1 -0.091194 0.096207 0.667180 11.00000 0.02256 0.02539 = 0.02114 -0.00484 0.00386 -0.00398 AFIX 43 H4 2 -0.106950 0.050679 0.662647 11.00000 -1.20000 AFIX 0 C6 1 0.022490 0.118975 0.708335 11.00000 0.02099 0.02248 = 0.01671 -0.00275 0.00375 -0.00128 C7 1 0.098145 0.075658 0.748698 11.00000 0.02476 0.01820 = 0.02043 -0.00215 0.00295 0.00042 AFIX 43 H5 2 0.082728 0.030037 0.744843 11.00000 -1.20000 AFIX 0 C8 1 0.192843 0.099056 0.792992 11.00000 0.02478 0.01979 = 0.01789 0.00105 0.00168 0.00252 AFIX 43 H6 2 0.234613 0.070436 0.822189 11.00000 -1.20000 AFIX 0 C9 1 0.227424 0.165965 0.794690 11.00000 0.01893 0.02030 = 0.01551 -0.00108 0.00078 0.00210 C10 1 0.171125 0.208863 0.751801 11.00000 0.01828 0.01785 = 0.01398 -0.00140 0.00271 0.00159 C11 1 0.248512 0.272805 0.761144 11.00000 0.01714 0.01912 = 0.01501 -0.00221 -0.00078 0.00275 C12 1 0.324464 0.269801 0.816062 11.00000 0.02013 0.01942 = 0.01524 0.00089 -0.00105 0.00198 C13 1 0.390825 0.325067 0.842932 11.00000 0.02294 0.02404 = 0.01578 -0.00276 -0.00405 0.00067 AFIX 43 H7 2 0.444267 0.321544 0.879893 11.00000 -1.20000 AFIX 0 C14 1 0.377231 0.384040 0.815001 11.00000 0.02704 0.02039 = 0.01743 -0.00347 -0.00351 -0.00196 AFIX 43 H8 2 0.413362 0.422238 0.834502 11.00000 -1.20000 AFIX 0 C15 1 0.309709 0.389069 0.757101 11.00000 0.02244 0.02048 = 0.01879 -0.00157 -0.00145 0.00068 C16 1 0.259470 0.331285 0.726359 11.00000 0.01860 0.01788 = 0.01754 -0.00092 -0.00013 0.00251 C17 1 0.222264 0.339365 0.664326 11.00000 0.01716 0.01739 = 0.01669 -0.00038 -0.00007 0.00098 C18 1 0.189417 0.401617 0.642957 11.00000 0.02130 0.01925 = 0.01689 0.00034 0.00016 0.00139 C19 1 0.221790 0.458161 0.675559 11.00000 0.02850 0.01683 = 0.02112 0.00132 -0.00271 0.00225 AFIX 43 H9 2 0.196573 0.499927 0.660099 11.00000 -1.20000 AFIX 0 C20 1 0.291287 0.451660 0.730739 11.00000 0.03019 0.01774 = 0.01969 -0.00353 -0.00081 -0.00026 AFIX 43 H10 2 0.327108 0.489249 0.751289 11.00000 -1.20000 AFIX 0 C21 1 0.256158 0.228159 0.605227 11.00000 0.01618 0.01769 = 0.01523 0.00084 0.00295 -0.00032 C22 1 0.364323 0.195790 0.643165 11.00000 0.01844 0.02154 = 0.01585 0.00049 0.00087 0.00046 AFIX 43 H11 2 0.411910 0.219001 0.674968 11.00000 -1.20000 AFIX 0 C23 1 0.400722 0.131275 0.634294 11.00000 0.02016 0.02009 = 0.01866 0.00248 0.00263 0.00347 AFIX 43 H12 2 0.471433 0.110076 0.660503 11.00000 -1.20000 AFIX 0 C24 1 0.333821 0.096386 0.586575 11.00000 0.02249 0.01593 = 0.02405 -0.00029 0.00512 0.00231 AFIX 43 H13 2 0.355645 0.051320 0.581860 11.00000 -1.20000 AFIX 0 C25 1 0.237322 0.127412 0.546974 11.00000 0.02252 0.01939 = 0.01919 -0.00260 0.00409 -0.00249 AFIX 43 H14 2 0.195344 0.103791 0.514282 11.00000 -1.20000 AFIX 0 C26 1 0.199083 0.194189 0.553981 11.00000 0.01754 0.01831 = 0.01805 -0.00009 0.00285 -0.00175 C27 1 0.109818 0.228188 0.510527 11.00000 0.02043 0.02404 = 0.01782 -0.00092 -0.00131 -0.00172 AFIX 43 H15 2 0.069386 0.205083 0.477247 11.00000 -1.20000 AFIX 0 C28 1 0.080956 0.293536 0.515674 11.00000 0.01933 0.02302 = 0.01546 0.00125 -0.00166 0.00113 AFIX 43 H16 2 0.029103 0.316517 0.484714 11.00000 -1.20000 AFIX 0 C29 1 0.129574 0.325990 0.567696 11.00000 0.01810 0.01874 = 0.01754 0.00139 0.00022 0.00051 C30 1 0.205020 0.293529 0.613782 11.00000 0.01780 0.01887 = 0.01517 0.00119 0.00020 -0.00009 C31 1 0.325803 0.201004 0.840360 11.00000 0.02064 0.01879 = 0.01472 -0.00053 -0.00097 0.00133 C32 1 0.264849 0.195542 0.904330 11.00000 0.02123 0.01512 = 0.01552 -0.00036 0.00059 0.00000 C33 1 0.117950 0.210126 0.926012 11.00000 0.02124 0.01955 = 0.02310 -0.00186 0.00018 0.00135 AFIX 43 H17 2 0.038356 0.225593 0.900167 11.00000 -1.20000 AFIX 0 C34 1 0.089315 0.201574 0.986859 11.00000 0.02632 0.02020 = 0.02415 -0.00155 0.00783 0.00213 AFIX 43 H18 2 -0.011684 0.210192 1.002408 11.00000 -1.20000 AFIX 0 C35 1 0.207480 0.180529 1.024936 11.00000 0.03158 0.02079 = 0.01570 -0.00261 0.00455 -0.00276 AFIX 43 H19 2 0.186783 0.176246 1.066356 11.00000 -1.20000 AFIX 0 C36 1 0.355647 0.165663 1.003159 11.00000 0.02575 0.02106 = 0.01538 0.00121 -0.00198 -0.00469 AFIX 43 H20 2 0.435673 0.150847 1.029130 11.00000 -1.20000 AFIX 0 C37 1 0.383238 0.173089 0.942415 11.00000 0.01961 0.01432 = 0.01802 -0.00015 -0.00052 -0.00253 C38 1 0.523454 0.160938 0.907117 11.00000 0.02049 0.01548 = 0.01762 0.00076 -0.00153 -0.00108 C39 1 0.669674 0.137673 0.924244 11.00000 0.02095 0.01958 = 0.02412 0.00239 -0.00374 -0.00080 AFIX 43 H21 2 0.691443 0.127985 0.964812 11.00000 -1.20000 AFIX 0 C40 1 0.782832 0.129000 0.880499 11.00000 0.01825 0.02033 = 0.03823 0.00117 0.00107 0.00177 AFIX 43 H22 2 0.883088 0.113170 0.891263 11.00000 -1.20000 AFIX 0 C41 1 0.750597 0.143276 0.821196 11.00000 0.02372 0.02625 = 0.03306 -0.00029 0.00948 0.00143 AFIX 43 H23 2 0.829152 0.136759 0.791923 11.00000 -1.20000 AFIX 0 C42 1 0.605003 0.166999 0.803882 11.00000 0.02709 0.02643 = 0.01943 0.00009 0.00459 0.00146 AFIX 43 H24 2 0.583787 0.176986 0.763332 11.00000 -1.20000 AFIX 0 C43 1 0.491931 0.175627 0.847474 11.00000 0.02046 0.01642 = 0.01864 0.00110 0.00024 0.00073 C44 1 0.113520 0.398050 0.581915 11.00000 0.01945 0.01889 = 0.01697 0.00085 -0.00172 0.00165 C45 1 0.183962 0.442937 0.535091 11.00000 0.02540 0.01567 = 0.01604 -0.00161 -0.00564 -0.00080 C46 1 0.332526 0.441035 0.511274 11.00000 0.02558 0.02065 = 0.01947 -0.00039 -0.00241 0.00199 AFIX 43 H25 2 0.405540 0.409124 0.523997 11.00000 -1.20000 AFIX 0 C47 1 0.373062 0.486978 0.468135 11.00000 0.03041 0.02522 = 0.01891 -0.00146 -0.00122 -0.00229 AFIX 43 H26 2 0.475005 0.486663 0.451523 11.00000 -1.20000 AFIX 0 C48 1 0.265087 0.533309 0.449253 11.00000 0.03754 0.02003 = 0.01834 0.00159 -0.00525 -0.00627 AFIX 43 H27 2 0.294097 0.563937 0.419510 11.00000 -1.20000 AFIX 0 C49 1 0.115484 0.535469 0.473230 11.00000 0.03387 0.01701 = 0.02061 0.00046 -0.01075 0.00020 AFIX 43 H28 2 0.042280 0.567164 0.460220 11.00000 -1.20000 AFIX 0 C50 1 0.075520 0.489964 0.516849 11.00000 0.02743 0.01584 = 0.01793 -0.00361 -0.00706 0.00098 C51 1 -0.070733 0.479433 0.549463 11.00000 0.02622 0.01614 = 0.01968 -0.00291 -0.00764 0.00200 C52 1 -0.211423 0.513274 0.548454 11.00000 0.02801 0.01803 = 0.02625 -0.00486 -0.00969 0.00426 AFIX 43 H29 2 -0.223592 0.550556 0.523810 11.00000 -1.20000 AFIX 0 C53 1 -0.333544 0.491828 0.583906 11.00000 0.02318 0.02424 = 0.03146 -0.00847 -0.00755 0.00682 AFIX 43 H30 2 -0.429304 0.515118 0.584009 11.00000 -1.20000 AFIX 0 C54 1 -0.317483 0.436322 0.619520 11.00000 0.02328 0.02724 = 0.02668 -0.00574 -0.00262 0.00287 AFIX 43 H31 2 -0.402990 0.421717 0.642912 11.00000 -1.20000 AFIX 0 C55 1 -0.176731 0.402277 0.620912 11.00000 0.02513 0.02387 = 0.02207 -0.00067 -0.00109 0.00458 AFIX 43 H32 2 -0.165009 0.364732 0.645251 11.00000 -1.20000 AFIX 0 C56 1 -0.054013 0.424498 0.585905 11.00000 0.02168 0.01806 = 0.01780 -0.00474 -0.00463 0.00283 CL1 3 0.840547 0.439550 0.857561 11.00000 0.09166 0.03417 = 0.03397 -0.00334 0.00374 -0.01865 CL2 3 0.821673 0.308237 0.809118 11.00000 0.06178 0.03874 = 0.05515 -0.01436 0.02232 -0.00563 PART 1 C58 1 0.931661 0.378333 0.811097 21.00000 0.04915 AFIX 23 H33 2 0.943939 0.395531 0.770134 21.00000 -1.20000 H34 2 1.036787 0.368231 0.826861 21.00000 -1.20000 PART 2 AFIX 0 C59 1 0.855974 0.391774 0.792585 -21.00000 0.04534 AFIX 23 H35 2 0.961526 0.396851 0.775285 -21.00000 -1.20000 H36 2 0.779051 0.406946 0.762738 -21.00000 -1.20000 PART 0 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 201029yanagi_a.res in P2(1)2(1)2(1) REM R1 = 0.0366 for 7638 Fo > 4sig(Fo) and 0.0373 for all 7819 data REM 532 parameters refined using 12 restraints END WGHT 0.0586 1.9160 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.482, deepest hole -0.701, 1-sigma level 0.048 Q1 1 0.7478 0.3338 0.7809 11.00000 0.05 0.48 Q2 1 0.9398 0.3395 0.8243 11.00000 0.05 0.37 Q3 1 0.9445 0.4143 0.8469 11.00000 0.05 0.36 Q4 1 0.7781 0.3952 0.7897 11.00000 0.05 0.26 Q5 1 0.7250 0.4504 0.8488 11.00000 0.05 0.25 Q6 1 0.3281 0.2371 0.8305 11.00000 0.05 0.19 Q7 1 -0.3177 0.4606 0.5980 11.00000 0.05 0.19 Q8 1 0.0192 0.1492 0.7143 11.00000 0.05 0.18 Q9 1 -0.1338 0.4906 0.5468 11.00000 0.05 0.17 Q10 1 0.2684 0.3005 0.7404 11.00000 0.05 0.17 Q11 1 -0.0641 0.4560 0.5746 11.00000 0.05 0.17 Q12 1 0.1599 0.4198 0.5626 11.00000 0.05 0.17 Q13 1 0.2908 0.3603 0.7401 11.00000 0.05 0.16 Q14 1 0.6377 0.3252 0.7313 11.00000 0.05 0.16 Q15 1 0.4121 0.1851 0.8418 11.00000 0.05 0.16 Q16 1 0.6635 0.3992 0.7804 11.00000 0.05 0.15 Q17 1 0.2231 0.2598 0.6135 11.00000 0.05 0.15 Q18 1 0.0019 0.4964 0.5353 11.00000 0.05 0.15 Q19 1 0.2108 0.2425 0.7478 11.00000 0.05 0.14 Q20 1 0.9518 0.0998 0.8367 11.00000 0.05 0.14 ; _shelx_res_checksum 53337 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_200221yanagi _audit_block_doi 10.5517/ccdc.csd.cc26qjn4 _database_code_depnum_ccdc_archive 'CCDC 2047446' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1SC00044F 2021 loop_ _audit_author_name _audit_author_address 'Tomoyuki Yanagi' ;Kyoto university Japan ; _audit_update_record ; 2020-12-01 deposited with the CCDC. 2021-02-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H8 O2 S' _chemical_formula_sum 'C15 H8 O2 S' _chemical_formula_weight 252.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 2/c' _space_group_name_Hall '-C 2yc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.7976(2) _cell_length_b 10.47210(10) _cell_length_c 11.73880(10) _cell_angle_alpha 90 _cell_angle_beta 99.1580(10) _cell_angle_gamma 90 _cell_volume 2159.97(4) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 12257 _cell_measurement_theta_min 3.8080 _cell_measurement_theta_max 74.2410 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_F_000 1040 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.220 _exptl_absorpt_coefficient_mu 2.567 _shelx_estimated_absorpt_T_min 0.578 _shelx_estimated_absorpt_T_max 0.602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72470 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 14066 _diffrn_reflns_av_unetI/netI 0.0100 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.916 _diffrn_reflns_theta_max 74.429 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 2181 _reflns_number_gt 2164 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+2.6888P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2181 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46749(8) 0.62494(13) 0.62101(11) 0.0123(3) Uani 1 1 d . . . . . C2 C 0.54376(8) 0.59930(14) 0.60692(12) 0.0134(3) Uani 1 1 d . . . . . H1 H 0.5624 0.5142 0.6145 0.016 Uiso 1 1 calc R U . . . C3 C 0.59104(8) 0.69559(14) 0.58248(12) 0.0152(3) Uani 1 1 d . . . . . H2 H 0.6422 0.6768 0.5746 0.018 Uiso 1 1 calc R U . . . C4 C 0.56404(9) 0.82261(14) 0.56897(13) 0.0165(3) Uani 1 1 d . . . . . H3 H 0.5977 0.8896 0.5561 0.020 Uiso 1 1 calc R U . . . C5 C 0.48949(9) 0.84896(14) 0.57440(13) 0.0163(3) Uani 1 1 d . . . . . H4 H 0.4713 0.9339 0.5617 0.020 Uiso 1 1 calc R U . . . C6 C 0.43882(8) 0.75208(14) 0.59855(12) 0.0137(3) Uani 1 1 d . . . . . C7 C 0.36065(8) 0.78020(14) 0.59872(12) 0.0157(3) Uani 1 1 d . . . . . H5 H 0.3432 0.8657 0.5881 0.019 Uiso 1 1 calc R U . . . C8 C 0.31039(8) 0.68518(14) 0.61398(13) 0.0157(3) Uani 1 1 d . . . . . H6 H 0.2574 0.7018 0.6077 0.019 Uiso 1 1 calc R U . . . C9 C 0.33979(8) 0.56268(14) 0.63921(12) 0.0136(3) Uani 1 1 d . . . . . C10 C 0.41638(8) 0.53169(13) 0.65333(11) 0.0124(3) Uani 1 1 d . . . . . C11 C 0.43090(8) 0.39900(14) 0.69809(12) 0.0130(3) Uani 1 1 d . . . . . C12 C 0.36458(8) 0.32729(14) 0.68673(12) 0.0142(3) Uani 1 1 d . . . . . C13 C 0.36171(9) 0.19505(14) 0.70479(13) 0.0167(3) Uani 1 1 d . . . . . H7 H 0.3146 0.1510 0.6999 0.020 Uiso 1 1 calc R U . . . C14 C 0.42996(9) 0.13214(14) 0.72982(13) 0.0169(3) Uani 1 1 d . . . . . H8 H 0.4304 0.0415 0.7337 0.020 Uiso 1 1 calc R U . . . C15 C 0.5000 0.1999(2) 0.7500 0.0154(4) Uani 1 2 d S T P . . C16 C 0.5000 0.33794(19) 0.7500 0.0133(4) Uani 1 2 d S T P . . S1 S 0.28412(2) 0.42712(3) 0.65306(3) 0.01465(14) Uani 1 1 d . . . . . O1 O 0.23907(6) 0.39708(11) 0.54335(10) 0.0221(3) Uani 1 1 d . . . . . O2 O 0.24524(7) 0.43549(10) 0.75156(11) 0.0228(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0128(7) 0.0129(7) 0.0106(6) -0.0007(5) 0.0000(5) -0.0014(5) C2 0.0131(7) 0.0150(7) 0.0118(6) 0.0000(5) 0.0010(5) 0.0001(5) C3 0.0117(7) 0.0195(7) 0.0145(7) 0.0009(5) 0.0027(5) -0.0004(5) C4 0.0150(7) 0.0161(7) 0.0185(7) 0.0017(5) 0.0028(5) -0.0041(5) C5 0.0177(7) 0.0130(7) 0.0180(7) 0.0026(5) 0.0025(5) -0.0004(6) C6 0.0134(7) 0.0143(7) 0.0132(6) 0.0000(5) 0.0014(5) -0.0009(5) C7 0.0147(7) 0.0141(7) 0.0178(7) 0.0017(5) 0.0013(5) 0.0020(5) C8 0.0107(7) 0.0182(7) 0.0178(7) 0.0017(5) 0.0014(5) 0.0016(5) C9 0.0115(7) 0.0144(7) 0.0144(7) -0.0002(5) 0.0009(5) -0.0026(5) C10 0.0118(7) 0.0131(7) 0.0119(6) -0.0017(5) 0.0008(5) -0.0005(5) C11 0.0135(7) 0.0131(6) 0.0128(6) -0.0016(5) 0.0034(5) -0.0014(5) C12 0.0128(7) 0.0146(7) 0.0155(7) -0.0011(5) 0.0033(5) -0.0014(5) C13 0.0170(8) 0.0149(7) 0.0188(7) -0.0010(5) 0.0047(6) -0.0050(6) C14 0.0220(8) 0.0102(7) 0.0189(7) 0.0001(5) 0.0042(6) -0.0021(5) C15 0.0193(11) 0.0126(10) 0.0145(9) 0.000 0.0035(8) 0.000 C16 0.0142(10) 0.0121(9) 0.0141(9) 0.000 0.0044(7) 0.000 S1 0.0099(2) 0.0139(2) 0.0204(2) -0.00040(12) 0.00338(15) -0.00208(11) O1 0.0136(5) 0.0233(6) 0.0277(6) -0.0027(5) -0.0025(4) -0.0033(4) O2 0.0205(6) 0.0207(6) 0.0305(6) 0.0017(5) 0.0142(5) -0.0003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.419(2) . ? C1 C10 1.4264(19) . ? C1 C6 1.435(2) . ? C2 C3 1.373(2) . ? C2 H1 0.9500 . ? C3 C4 1.415(2) . ? C3 H2 0.9500 . ? C4 C5 1.366(2) . ? C4 H3 0.9500 . ? C5 C6 1.416(2) . ? C5 H4 0.9500 . ? C6 C7 1.422(2) . ? C7 C8 1.369(2) . ? C7 H5 0.9500 . ? C8 C9 1.399(2) . ? C8 H6 0.9500 . ? C9 C10 1.385(2) . ? C9 S1 1.7534(14) . ? C10 C11 1.4935(19) . ? C11 C12 1.387(2) . ? C11 C16 1.4333(17) . ? C12 C13 1.403(2) . ? C12 S1 1.7663(15) . ? C13 C14 1.372(2) . ? C13 H7 0.9500 . ? C14 C15 1.4212(18) . ? C14 H8 0.9500 . ? C15 C14 1.4212(18) 2_656 ? C15 C16 1.445(3) . ? C16 C11 1.4333(17) 2_656 ? S1 O1 1.4393(12) . ? S1 O2 1.4415(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 124.32(13) . . ? C2 C1 C6 118.22(13) . . ? C10 C1 C6 117.44(13) . . ? C3 C2 C1 121.00(14) . . ? C3 C2 H1 119.5 . . ? C1 C2 H1 119.5 . . ? C2 C3 C4 120.37(14) . . ? C2 C3 H2 119.8 . . ? C4 C3 H2 119.8 . . ? C5 C4 C3 119.98(14) . . ? C5 C4 H3 120.0 . . ? C3 C4 H3 120.0 . . ? C4 C5 C6 121.25(14) . . ? C4 C5 H4 119.4 . . ? C6 C5 H4 119.4 . . ? C5 C6 C7 120.42(13) . . ? C5 C6 C1 118.84(13) . . ? C7 C6 C1 120.74(13) . . ? C8 C7 C6 120.62(14) . . ? C8 C7 H5 119.7 . . ? C6 C7 H5 119.7 . . ? C7 C8 C9 117.66(13) . . ? C7 C8 H6 121.2 . . ? C9 C8 H6 121.2 . . ? C10 C9 C8 124.59(13) . . ? C10 C9 S1 111.04(11) . . ? C8 C9 S1 124.35(11) . . ? C9 C10 C1 117.70(13) . . ? C9 C10 C11 111.83(12) . . ? C1 C10 C11 130.43(13) . . ? C12 C11 C16 117.30(14) . . ? C12 C11 C10 111.90(13) . . ? C16 C11 C10 130.80(14) . . ? C11 C12 C13 124.79(14) . . ? C11 C12 S1 110.37(11) . . ? C13 C12 S1 124.77(11) . . ? C14 C13 C12 117.00(13) . . ? C14 C13 H7 121.5 . . ? C12 C13 H7 121.5 . . ? C13 C14 C15 121.27(14) . . ? C13 C14 H8 119.4 . . ? C15 C14 H8 119.4 . . ? C14 C15 C14 120.07(19) . 2_656 ? C14 C15 C16 119.96(9) . . ? C14 C15 C16 119.96(9) 2_656 . ? C11 C16 C11 127.01(19) . 2_656 ? C11 C16 C15 116.50(9) . . ? C11 C16 C15 116.50(9) 2_656 . ? O1 S1 O2 117.44(7) . . ? O1 S1 C9 109.66(7) . . ? O2 S1 C9 112.06(7) . . ? O1 S1 C12 112.78(7) . . ? O2 S1 C12 109.39(7) . . ? C9 S1 C12 92.87(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -176.00(13) . . . . ? C6 C1 C2 C3 5.7(2) . . . . ? C1 C2 C3 C4 -1.0(2) . . . . ? C2 C3 C4 C5 -3.3(2) . . . . ? C3 C4 C5 C6 2.9(2) . . . . ? C4 C5 C6 C7 -177.16(13) . . . . ? C4 C5 C6 C1 1.9(2) . . . . ? C2 C1 C6 C5 -6.05(19) . . . . ? C10 C1 C6 C5 175.51(13) . . . . ? C2 C1 C6 C7 172.99(13) . . . . ? C10 C1 C6 C7 -5.4(2) . . . . ? C5 C6 C7 C8 175.39(14) . . . . ? C1 C6 C7 C8 -3.6(2) . . . . ? C6 C7 C8 C9 5.4(2) . . . . ? C7 C8 C9 C10 2.1(2) . . . . ? C7 C8 C9 S1 -176.00(11) . . . . ? C8 C9 C10 C1 -11.2(2) . . . . ? S1 C9 C10 C1 167.14(10) . . . . ? C8 C9 C10 C11 170.78(13) . . . . ? S1 C9 C10 C11 -10.90(15) . . . . ? C2 C1 C10 C9 -166.04(13) . . . . ? C6 C1 C10 C9 12.29(19) . . . . ? C2 C1 C10 C11 11.6(2) . . . . ? C6 C1 C10 C11 -170.10(13) . . . . ? C9 C10 C11 C12 15.67(17) . . . . ? C1 C10 C11 C12 -162.06(14) . . . . ? C9 C10 C11 C16 -163.52(13) . . . . ? C1 C10 C11 C16 18.8(2) . . . . ? C16 C11 C12 C13 -10.8(2) . . . . ? C10 C11 C12 C13 169.92(14) . . . . ? C16 C11 C12 S1 166.45(9) . . . . ? C10 C11 C12 S1 -12.86(14) . . . . ? C11 C12 C13 C14 -3.4(2) . . . . ? S1 C12 C13 C14 179.76(11) . . . . ? C12 C13 C14 C15 7.3(2) . . . . ? C13 C14 C15 C14 -176.92(16) . . . 2_656 ? C13 C14 C15 C16 3.08(16) . . . . ? C12 C11 C16 C11 -159.72(13) . . . 2_656 ? C10 C11 C16 C11 19.43(12) . . . 2_656 ? C12 C11 C16 C15 20.28(13) . . . . ? C10 C11 C16 C15 -160.57(12) . . . . ? C14 C15 C16 C11 -17.02(9) . . . . ? C14 C15 C16 C11 162.98(9) 2_656 . . . ? C14 C15 C16 C11 162.98(9) . . . 2_656 ? C14 C15 C16 C11 -17.02(9) 2_656 . . 2_656 ? C10 C9 S1 O1 -112.23(11) . . . . ? C8 C9 S1 O1 66.10(14) . . . . ? C10 C9 S1 O2 115.49(11) . . . . ? C8 C9 S1 O2 -66.19(14) . . . . ? C10 C9 S1 C12 3.21(11) . . . . ? C8 C9 S1 C12 -178.46(13) . . . . ? C11 C12 S1 O1 118.60(11) . . . . ? C13 C12 S1 O1 -64.18(15) . . . . ? C11 C12 S1 O2 -108.74(11) . . . . ? C13 C12 S1 O2 68.48(14) . . . . ? C11 C12 S1 C9 5.87(11) . . . . ? C13 C12 S1 C9 -176.91(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H7 O2 0.95 2.60 3.4036(18) 142.8 4_546 _refine_diff_density_max 0.294 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.122 _shelx_res_file ; 200221yanagi.res created by SHELXL-2014/7 TITL 200221yanagi_a.res in C2/c REM Yadorkari-X generated CELL 1.54184 17.7976 10.4721 11.7388 90.0000 99.1580 90.0000 ZERR 8.0 0.0002 0.0001 0.0001 0.0000 0.0010 0.0000 LATT 7 SYMM -X, +Y, 1/2-Z REM SPGR C2/c monoclinic SFAC C H S O UNIT 120 64 8 16 SIZE 0.24 0.22 0.22 TEMP -180.0 L.S. 30 FMAP 2 PLAN -20 ACTA CONF HTAB LIST 4 BOND $H MERG 2 EQIV $1 1/2-X, -1/2+Y, 3/2-Z HTAB C13 O2_$1 WGHT 0.059100 2.688800 FVAR 3.88212 C1 1 0.467489 0.624937 0.621009 11.00000 0.01277 0.01287 = 0.01055 -0.00074 -0.00001 -0.00144 C2 1 0.543759 0.599299 0.606919 11.00000 0.01307 0.01499 = 0.01180 0.00003 0.00104 0.00015 AFIX 43 H1 2 0.562381 0.514204 0.614518 11.00000 -1.20000 AFIX 0 C3 1 0.591036 0.695593 0.582476 11.00000 0.01175 0.01952 = 0.01453 0.00092 0.00272 -0.00043 AFIX 43 H2 2 0.642179 0.676831 0.574587 11.00000 -1.20000 AFIX 0 C4 1 0.564038 0.822612 0.568967 11.00000 0.01498 0.01609 = 0.01854 0.00175 0.00277 -0.00405 AFIX 43 H3 2 0.597718 0.889570 0.556121 11.00000 -1.20000 AFIX 0 C5 1 0.489494 0.848961 0.574401 11.00000 0.01771 0.01298 = 0.01797 0.00257 0.00251 -0.00044 AFIX 43 H4 2 0.471328 0.933899 0.561736 11.00000 -1.20000 AFIX 0 C6 1 0.438817 0.752075 0.598548 11.00000 0.01336 0.01431 = 0.01316 0.00005 0.00140 -0.00086 C7 1 0.360645 0.780200 0.598717 11.00000 0.01473 0.01407 = 0.01782 0.00167 0.00132 0.00197 AFIX 43 H5 2 0.343153 0.865741 0.588136 11.00000 -1.20000 AFIX 0 C8 1 0.310395 0.685178 0.613981 11.00000 0.01068 0.01820 = 0.01780 0.00169 0.00136 0.00155 AFIX 43 H6 2 0.257420 0.701811 0.607669 11.00000 -1.20000 AFIX 0 C9 1 0.339786 0.562680 0.639207 11.00000 0.01149 0.01444 = 0.01444 -0.00019 0.00091 -0.00259 C10 1 0.416380 0.531695 0.653330 11.00000 0.01181 0.01314 = 0.01189 -0.00169 0.00081 -0.00047 C11 1 0.430896 0.398999 0.698091 11.00000 0.01346 0.01311 = 0.01282 -0.00162 0.00337 -0.00140 C12 1 0.364579 0.327288 0.686735 11.00000 0.01285 0.01456 = 0.01552 -0.00115 0.00325 -0.00143 C13 1 0.361710 0.195047 0.704790 11.00000 0.01699 0.01486 = 0.01880 -0.00097 0.00474 -0.00500 AFIX 43 H7 2 0.314625 0.151050 0.699903 11.00000 -1.20000 AFIX 0 C14 1 0.429961 0.132144 0.729819 11.00000 0.02204 0.01022 = 0.01886 0.00006 0.00415 -0.00214 AFIX 43 H8 2 0.430412 0.041530 0.733735 11.00000 -1.20000 AFIX 0 C15 1 0.500000 0.199924 0.750000 10.50000 0.01926 0.01260 = 0.01447 0.00000 0.00351 0.00000 C16 1 0.500000 0.337939 0.750000 10.50000 0.01422 0.01214 = 0.01408 0.00000 0.00437 0.00000 S1 3 0.284120 0.427122 0.653064 11.00000 0.00992 0.01392 = 0.02041 -0.00040 0.00338 -0.00208 O1 4 0.239072 0.397079 0.543354 11.00000 0.01355 0.02330 = 0.02766 -0.00273 -0.00247 -0.00328 O2 4 0.245240 0.435488 0.751557 11.00000 0.02046 0.02071 = 0.03051 0.00170 0.01418 -0.00025 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 200221yanagi_a.res in C2/c REM R1 = 0.0360 for 2164 Fo > 4sig(Fo) and 0.0362 for all 2181 data REM 164 parameters refined using 0 restraints END WGHT 0.0538 2.6644 REM Instructions for potential hydrogen bonds HTAB C13 O2_$1 REM Highest difference peak 0.294, deepest hole -0.631, 1-sigma level 0.122 Q1 1 0.4645 0.7773 0.7451 11.00000 0.05 0.29 Q2 1 0.3474 0.6175 0.3814 11.00000 0.05 0.29 Q3 1 0.5491 0.8909 0.7570 11.00000 0.05 0.29 Q4 1 0.5311 0.8649 0.7420 11.00000 0.05 0.29 Q5 1 0.3958 0.6444 0.4097 11.00000 0.05 0.28 Q6 1 0.4187 0.7507 0.3949 11.00000 0.05 0.28 Q7 1 0.3777 0.6868 0.3796 11.00000 0.05 0.28 Q8 1 0.3825 0.7228 0.3958 11.00000 0.05 0.28 Q9 1 0.4590 0.7752 0.4152 11.00000 0.05 0.27 Q10 1 0.3113 0.7061 0.3717 11.00000 0.05 0.27 Q11 1 0.5781 0.8215 0.7393 11.00000 0.05 0.24 Q12 1 0.3578 0.2190 0.8618 11.00000 0.05 0.24 Q13 1 0.4875 0.7359 0.7162 11.00000 0.05 0.24 Q14 1 0.2819 0.2842 0.5149 11.00000 0.05 0.23 Q15 1 0.4895 0.3213 0.5935 11.00000 0.05 0.23 Q16 1 0.4663 0.6841 0.4355 11.00000 0.05 0.23 Q17 1 0.3226 0.5766 0.4152 11.00000 0.05 0.22 Q18 1 0.5878 0.7026 0.7380 11.00000 0.05 0.22 Q19 1 0.5471 0.7310 0.4404 11.00000 0.05 0.21 Q20 1 0.5974 0.7594 0.4523 11.00000 0.05 0.21 ; _shelx_res_checksum 79321 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_91119yuk _database_code_depnum_ccdc_archive 'CCDC 2047441' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1SC00044F 2021 loop_ _audit_author_name _audit_author_address 'Tomoyuki Yanagi' ;Kyoto university Japan ; _audit_update_record ; 2021-02-02 deposited with the CCDC. 2021-02-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C30 H16 S2)' _chemical_formula_sum 'C120 H64 S8' _chemical_formula_weight 1762.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 17.272(2) _cell_length_b 14.9852(13) _cell_length_c 17.311(2) _cell_angle_alpha 90 _cell_angle_beta 114.511(3) _cell_angle_gamma 90 _cell_volume 4076.7(8) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4108 _cell_measurement_theta_min 27.8 _cell_measurement_theta_max 74.1 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_F_000 1824 _exptl_transmission_factor_min 0.761 _exptl_transmission_factor_max 0.975 _exptl_crystal_size_max 0.110 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.010 _exptl_absorpt_coefficient_mu 2.482 _shelx_estimated_absorpt_T_min 0.772 _shelx_estimated_absorpt_T_max 0.976 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 106408 _diffrn_reflns_av_unetI/netI 0.0270 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.812 _diffrn_reflns_theta_max 68.282 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_point_group_measured_fraction_full 0.991 _reflns_number_total 14733 _reflns_number_gt 13987 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.903 _reflns_Friedel_fraction_max 0.976 _reflns_Friedel_fraction_full 0.982 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+6.9547P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 6035 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.050(3) _chemical_absolute_configuration ? _refine_ls_number_reflns 14733 _refine_ls_number_parameters 1153 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1369 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S5 S 0.50166(10) 0.39825(11) 0.49827(9) 0.0342(3) Uani 1 1 d . . . . . S1 S -0.47675(9) 0.79296(10) 0.68871(10) 0.0343(3) Uani 1 1 d . . . . . S6 S 0.97723(10) 0.31078(11) 0.78007(10) 0.0369(4) Uani 1 1 d . . . . . S3 S 0.19894(11) 0.71125(10) 0.52677(9) 0.0365(4) Uani 1 1 d . . . . . S4 S 0.51377(10) 0.59437(11) 0.98410(10) 0.0384(4) Uani 1 1 d . . . . . S7 S 1.28890(11) 0.18729(11) 0.98109(10) 0.0389(4) Uani 1 1 d . . . . . S2 S -0.02205(10) 0.89625(11) 1.02002(9) 0.0376(4) Uani 1 1 d . . . . . S8 S 0.99460(12) 0.11519(11) 0.50759(10) 0.0423(4) Uani 1 1 d . . . . . C48 C 0.6252(4) 0.3751(3) 0.6484(3) 0.0224(11) Uani 1 1 d . . . . . C49 C -0.3164(4) 0.7502(3) 0.7615(3) 0.0222(11) Uani 1 1 d . . . . . C50 C -0.1805(4) 0.8797(3) 0.9096(3) 0.0235(12) Uani 1 1 d . . . . . C51 C 0.7524(4) 0.3781(3) 0.6008(3) 0.0219(11) Uani 1 1 d . . . . . C52 C 0.2675(4) 0.7494(3) 0.6884(3) 0.0223(11) Uani 1 1 d . . . . . C53 C 0.2088(3) 0.6044(3) 0.7640(3) 0.0226(11) Uani 1 1 d . . . . . H1 H 0.2287 0.5850 0.7232 0.027 Uiso 1 1 calc R U . . . C54 C -0.1516(4) 0.8688(4) 0.7721(3) 0.0250(12) Uani 1 1 d . . . . . C55 C -0.2310(4) 0.8960(4) 0.7114(3) 0.0248(11) Uani 1 1 d . . . . . H2 H -0.2733 0.9154 0.7293 0.030 Uiso 1 1 calc R U . . . C56 C 0.2128(4) 0.8626(4) 0.7567(4) 0.0251(12) Uani 1 1 d . . . . . C57 C 0.7439(3) 0.4011(4) 0.7921(3) 0.0232(11) Uani 1 1 d . . . . . H3 H 0.7799 0.4229 0.7671 0.028 Uiso 1 1 calc R U . . . C58 C 1.2389(4) 0.1316(4) 0.6608(4) 0.0279(12) Uani 1 1 d . . . . . C59 C 0.6602(3) 0.3722(3) 0.7391(3) 0.0214(11) Uani 1 1 d . . . . . C60 C -0.2448(4) 0.6921(3) 0.7767(3) 0.0225(11) Uani 1 1 d . . . . . C61 C -0.1288(4) 0.8705(4) 0.8625(3) 0.0247(12) Uani 1 1 d . . . . . C62 C -0.3927(4) 0.6792(4) 0.6223(4) 0.0366(15) Uani 1 1 d . . . . . H4 H -0.4437 0.6731 0.5722 0.044 Uiso 1 1 calc R U . . . C63 C 0.4105(4) 0.6146(4) 0.8243(4) 0.0250(12) Uani 1 1 d . . . . . C64 C 0.6663(4) 0.3877(3) 0.5898(3) 0.0234(11) Uani 1 1 d . . . . . C65 C 0.2682(4) 0.6285(3) 0.8455(3) 0.0238(12) Uani 1 1 d . . . . . C66 C 0.2804(3) 0.8068(4) 0.7595(3) 0.0217(11) Uani 1 1 d . . . . . C67 C 0.6065(4) 0.3467(4) 0.7796(4) 0.0271(12) Uani 1 1 d . . . . . C68 C 0.7760(4) 0.4202(4) 0.5401(4) 0.0299(13) Uani 1 1 d . . . . . C69 C 0.2363(4) 0.6518(4) 0.9075(3) 0.0276(12) Uani 1 1 d . . . . . C70 C 0.3687(4) 0.8725(4) 0.8966(4) 0.0267(12) Uani 1 1 d . . . . . H5 H 0.4225 0.8788 0.9433 0.032 Uiso 1 1 calc R U . . . C71 C -0.2697(4) 0.8679(4) 0.8868(3) 0.0232(11) Uani 1 1 d . . . . . C72 C -0.2470(4) 0.6373(4) 0.7079(4) 0.0272(12) Uani 1 1 d . . . . . C73 C 1.2343(4) 0.2398(4) 0.8241(4) 0.0288(13) Uani 1 1 d . . . . . C74 C -0.3894(4) 0.7361(4) 0.6883(4) 0.0275(13) Uani 1 1 d . . . . . C75 C -0.0871(4) 0.8466(4) 0.7442(4) 0.0262(12) Uani 1 1 d . . . . . C76 C 0.8199(4) 0.3301(4) 0.6685(3) 0.0234(12) Uani 1 1 d . . . . . C77 C 0.1958(4) 0.7671(4) 0.6145(4) 0.0280(13) Uani 1 1 d . . . . . C78 C 1.0906(4) 0.1209(4) 0.6707(4) 0.0267(12) Uani 1 1 d . . . . . C79 C 1.2292(4) 0.3012(4) 0.7575(3) 0.0271(12) Uani 1 1 d . . . . . C80 C 1.1470(4) 0.1326(4) 0.6281(3) 0.0259(12) Uani 1 1 d . . . . . C81 C 0.4190(5) 0.5783(4) 0.6142(5) 0.0394(17) Uani 1 1 d . . . . . H6 H 0.4556 0.5496 0.5934 0.047 Uiso 1 1 calc R U . . . C82 C 0.7736(4) 0.3981(4) 0.8783(4) 0.0299(12) Uani 1 1 d . . . . . H7 H 0.8295 0.4187 0.9125 0.036 Uiso 1 1 calc R U . . . C83 C 0.5369(4) 0.3719(4) 0.6050(4) 0.0272(12) Uani 1 1 d . . . . . C84 C 1.1047(3) 0.1271(3) 0.7586(3) 0.0225(11) Uani 1 1 d . . . . . C85 C 0.7522(4) 0.2015(4) 0.7225(4) 0.0289(13) Uani 1 1 d . . . . . C86 C -0.3290(4) 0.8195(4) 0.8145(3) 0.0251(12) Uani 1 1 d . . . . . C87 C 1.3018(4) 0.2471(4) 0.9019(4) 0.0312(13) Uani 1 1 d . . . . . C88 C 0.8980(4) 0.2512(4) 0.7945(4) 0.0311(14) Uani 1 1 d . . . . . C89 C 0.6059(4) 0.4095(4) 0.5083(4) 0.0286(12) Uani 1 1 d . . . . . C90 C -0.1085(4) 0.8427(4) 0.6565(4) 0.0339(14) Uani 1 1 d . . . . . H8 H -0.0670 0.8231 0.6375 0.041 Uiso 1 1 calc R U . . . C91 C 1.2776(5) 0.1565(4) 0.6061(4) 0.0365(15) Uani 1 1 d . . . . . C92 C -0.0426(4) 0.8698(4) 0.9162(4) 0.0303(13) Uani 1 1 d . . . . . C93 C -0.3222(4) 0.6339(4) 0.6316(4) 0.0344(14) Uani 1 1 d . . . . . H9 H -0.3228 0.5985 0.5858 0.041 Uiso 1 1 calc R U . . . C94 C 1.0435(4) 0.0853(4) 0.7818(4) 0.0311(13) Uani 1 1 d . . . . . C95 C 0.1287(4) 0.8222(4) 0.6096(4) 0.0349(14) Uani 1 1 d . . . . . H10 H 0.0789 0.8277 0.5582 0.042 Uiso 1 1 calc R U . . . C96 C -0.1757(4) 0.6812(4) 0.8561(3) 0.0244(12) Uani 1 1 d . . . . . H11 H -0.1744 0.7140 0.9036 0.029 Uiso 1 1 calc R U . . . C97 C 0.1232(4) 0.6081(4) 0.7417(4) 0.0318(13) Uani 1 1 d . . . . . H12 H 0.0847 0.5904 0.6864 0.038 Uiso 1 1 calc R U . . . C98 C 1.0077(4) 0.1009(4) 0.6119(4) 0.0317(13) Uani 1 1 d . . . . . C99 C 0.6399(4) 0.3414(4) 0.8677(4) 0.0342(14) Uani 1 1 d . . . . . H13 H 0.6047 0.3209 0.8941 0.041 Uiso 1 1 calc R U . . . C100 C -0.3041(4) 0.9096(4) 0.9403(4) 0.0304(13) Uani 1 1 d . . . . . C101 C -0.2489(4) 0.8951(4) 0.6261(4) 0.0320(13) Uani 1 1 d . . . . . H14 H -0.3032 0.9141 0.5858 0.038 Uiso 1 1 calc R U . . . C102 C -0.4478(4) 0.8947(4) 0.8324(4) 0.0326(14) Uani 1 1 d . . . . . H15 H -0.5064 0.9101 0.8095 0.039 Uiso 1 1 calc R U . . . C103 C 1.2923(4) 0.0981(4) 0.7422(4) 0.0305(13) Uani 1 1 d . . . . . H16 H 1.2678 0.0757 0.7783 0.037 Uiso 1 1 calc R U . . . C104 C -0.4146(4) 0.8413(4) 0.7858(4) 0.0267(12) Uani 1 1 d . . . . . C105 C 0.7124(4) 0.4484(4) 0.4620(4) 0.0328(14) Uani 1 1 d . . . . . H17 H 0.7288 0.4746 0.4211 0.039 Uiso 1 1 calc R U . . . C106 C 0.3591(4) 0.8146(4) 0.8310(3) 0.0236(11) Uani 1 1 d . . . . . H18 H 0.4061 0.7796 0.8341 0.028 Uiso 1 1 calc R U . . . C107 C -0.1308(4) 0.9029(4) 0.9941(3) 0.0306(13) Uani 1 1 d . . . . . C108 C 0.8175(4) 0.2623(4) 0.7267(3) 0.0259(12) Uani 1 1 d . . . . . C109 C 0.4095(4) 0.6222(4) 0.9595(4) 0.0297(13) Uani 1 1 d . . . . . C110 C 0.1364(4) 0.8681(4) 0.6807(4) 0.0315(13) Uani 1 1 d . . . . . H19 H 0.0906 0.9039 0.6795 0.038 Uiso 1 1 calc R U . . . C111 C 0.4461(4) 0.5880(4) 0.7035(4) 0.0332(14) Uani 1 1 d . . . . . C112 C 0.9112(5) 0.1976(4) 0.8663(4) 0.0396(16) Uani 1 1 d . . . . . H20 H 0.9653 0.1953 0.9131 0.048 Uiso 1 1 calc R U . . . C113 C -0.1750(4) 0.5818(4) 0.7208(4) 0.0353(15) Uani 1 1 d . . . . . H21 H -0.1737 0.5487 0.6746 0.042 Uiso 1 1 calc R U . . . C114 C 0.3213(4) 0.6799(4) 0.6763(4) 0.0277(12) Uani 1 1 d . . . . . C115 C 0.3903(4) 0.6294(4) 0.7361(4) 0.0271(12) Uani 1 1 d . . . . . C116 C 0.5188(4) 0.3328(4) 0.7297(4) 0.0344(14) Uani 1 1 d . . . . . H22 H 0.4838 0.3117 0.7561 0.041 Uiso 1 1 calc R U . . . C117 C 0.8454(5) 0.1503(5) 0.8666(4) 0.0426(17) Uani 1 1 d . . . . . H23 H 0.8524 0.1176 0.9161 0.051 Uiso 1 1 calc R U . . . C118 C -0.1641(4) 0.9317(4) 1.0518(4) 0.0346(15) Uani 1 1 d . . . . . H24 H -0.1278 0.9453 1.1091 0.041 Uiso 1 1 calc R U . . . C119 C 0.8625(4) 0.4338(4) 0.5570(4) 0.0311(13) Uani 1 1 d . . . . . H25 H 0.8763 0.4625 0.5155 0.037 Uiso 1 1 calc R U . . . C120 C 0.3585(4) 0.6251(3) 0.8730(3) 0.0240(12) Uani 1 1 d . . . . . C121 C 0.3779(4) 0.6434(4) 1.0209(4) 0.0348(14) Uani 1 1 d . . . . . H26 H 0.4150 0.6456 1.0795 0.042 Uiso 1 1 calc R U . . . C122 C 1.3757(4) 0.3489(4) 0.8510(5) 0.0428(18) Uani 1 1 d . . . . . H27 H 1.4260 0.3806 0.8585 0.051 Uiso 1 1 calc R U . . . C123 C -0.1097(4) 0.6241(4) 0.8662(4) 0.0323(14) Uani 1 1 d . . . . . H28 H -0.0642 0.6174 0.9207 0.039 Uiso 1 1 calc R U . . . C124 C 0.6271(4) 0.4391(4) 0.4432(4) 0.0331(14) Uani 1 1 d . . . . . H29 H 0.5846 0.4523 0.3883 0.040 Uiso 1 1 calc R U . . . C125 C 0.9255(4) 0.4076(4) 0.6299(4) 0.0355(14) Uani 1 1 d . . . . . H30 H 0.9829 0.4241 0.6438 0.043 Uiso 1 1 calc R U . . . C126 C 0.6275(5) 0.0786(4) 0.7197(5) 0.0435(18) Uani 1 1 d . . . . . H31 H 0.5845 0.0389 0.7194 0.052 Uiso 1 1 calc R U . . . C127 C 0.2987(4) 0.9219(4) 0.8940(4) 0.0300(13) Uani 1 1 d . . . . . H32 H 0.3049 0.9592 0.9405 0.036 Uiso 1 1 calc R U . . . C128 C 1.1385(4) 0.0921(4) 0.9304(4) 0.0348(15) Uani 1 1 d . . . . . H33 H 1.1543 0.0738 0.9875 0.042 Uiso 1 1 calc R U . . . C129 C 0.7224(4) 0.3650(4) 0.9175(4) 0.0351(15) Uani 1 1 d . . . . . H34 H 0.7448 0.3592 0.9775 0.042 Uiso 1 1 calc R U . . . C130 C 1.3033(4) 0.3534(4) 0.7708(4) 0.0355(15) Uani 1 1 d . . . . . C131 C -0.1872(4) 0.8664(4) 0.5984(4) 0.0337(14) Uani 1 1 d . . . . . H35 H -0.2004 0.8635 0.5395 0.040 Uiso 1 1 calc R U . . . C132 C 0.2227(4) 0.9174(4) 0.8263(4) 0.0317(13) Uani 1 1 d . . . . . H36 H 0.1758 0.9511 0.8257 0.038 Uiso 1 1 calc R U . . . C133 C 1.1750(4) 0.1725(4) 0.8254(3) 0.0250(12) Uani 1 1 d . . . . . C134 C -0.0005(4) 0.8345(4) 0.8038(4) 0.0316(14) Uani 1 1 d . . . . . H37 H 0.0411 0.8159 0.7846 0.038 Uiso 1 1 calc R U . . . C135 C 0.7656(4) 0.1478(4) 0.7951(4) 0.0356(15) Uani 1 1 d . . . . . C136 C 0.9039(4) 0.3546(4) 0.6856(4) 0.0306(13) Uani 1 1 d . . . . . C137 C 0.2937(4) 0.6605(4) 0.9943(4) 0.0339(14) Uani 1 1 d . . . . . H38 H 0.2726 0.6787 1.0345 0.041 Uiso 1 1 calc R U . . . C138 C 1.3740(4) 0.3012(5) 0.9158(5) 0.0422(17) Uani 1 1 d . . . . . H39 H 1.4204 0.3034 0.9701 0.051 Uiso 1 1 calc R U . . . C139 C 0.3422(5) 0.6091(4) 0.5578(4) 0.0383(16) Uani 1 1 d . . . . . H40 H 0.3215 0.5956 0.4990 0.046 Uiso 1 1 calc R U . . . C140 C 1.2249(5) 0.1753(4) 0.5190(4) 0.0408(17) Uani 1 1 d . . . . . H41 H 1.2503 0.1985 0.4840 0.049 Uiso 1 1 calc R U . . . C141 C 0.2946(4) 0.6614(4) 0.5896(4) 0.0316(14) Uani 1 1 d . . . . . C142 C 0.0919(4) 0.6380(4) 0.8004(5) 0.0393(16) Uani 1 1 d . . . . . H42 H 0.0324 0.6444 0.7836 0.047 Uiso 1 1 calc R U . . . C143 C -0.1090(4) 0.5759(4) 0.7977(4) 0.0358(15) Uani 1 1 d . . . . . H43 H -0.0618 0.5388 0.8051 0.043 Uiso 1 1 calc R U . . . C144 C 1.1928(4) 0.1449(4) 0.9080(4) 0.0299(13) Uani 1 1 d . . . . . C145 C 0.4836(4) 0.3492(4) 0.6449(4) 0.0319(13) Uani 1 1 d . . . . . H44 H 0.4237 0.3453 0.6131 0.038 Uiso 1 1 calc R U . . . C146 C 0.1472(4) 0.6577(4) 0.8810(4) 0.0343(14) Uani 1 1 d . . . . . H45 H 0.1255 0.6760 0.9207 0.041 Uiso 1 1 calc R U . . . C147 C 1.0616(5) 0.0675(4) 0.8672(4) 0.0360(15) Uani 1 1 d . . . . . H46 H 1.0204 0.0383 0.8814 0.043 Uiso 1 1 calc R U . . . C148 C 1.1023(4) 0.1386(4) 0.5406(4) 0.0323(14) Uani 1 1 d . . . . . C149 C 0.9626(4) 0.0598(4) 0.7177(5) 0.0351(15) Uani 1 1 d . . . . . H47 H 0.9217 0.0335 0.7341 0.042 Uiso 1 1 calc R U . . . C150 C 1.1407(5) 0.1611(4) 0.4854(4) 0.0447(18) Uani 1 1 d . . . . . H48 H 1.1077 0.1661 0.4260 0.054 Uiso 1 1 calc R U . . . C151 C 1.1550(5) 0.3771(4) 0.6233(4) 0.0387(16) Uani 1 1 d . . . . . H49 H 1.1043 0.3875 0.5738 0.046 Uiso 1 1 calc R U . . . C152 C 0.6773(4) 0.1866(4) 0.6487(4) 0.0306(13) Uani 1 1 d . . . . . H50 H 0.6688 0.2192 0.5987 0.037 Uiso 1 1 calc R U . . . C153 C 1.1551(4) 0.3184(4) 0.6849(4) 0.0300(13) Uani 1 1 d . . . . . H51 H 1.1038 0.2890 0.6776 0.036 Uiso 1 1 calc R U . . . C154 C 0.0222(4) 0.8496(4) 0.8876(4) 0.0333(14) Uani 1 1 d . . . . . H52 H 0.0802 0.8469 0.9268 0.040 Uiso 1 1 calc R U . . . C155 C 0.4934(4) 0.5899(4) 0.8771(4) 0.0350(14) Uani 1 1 d . . . . . C156 C -0.3943(4) 0.9229(4) 0.9098(4) 0.0354(15) Uani 1 1 d . . . . . H53 H -0.4164 0.9522 0.9449 0.043 Uiso 1 1 calc R U . . . C157 C -0.2498(5) 0.9391(4) 1.0223(4) 0.0371(16) Uani 1 1 d . . . . . H54 H -0.2738 0.9647 1.0576 0.044 Uiso 1 1 calc R U . . . C158 C 0.5522(4) 0.5607(4) 0.8449(5) 0.0410(17) Uani 1 1 d . . . . . H55 H 0.6087 0.5449 0.8822 0.049 Uiso 1 1 calc R U . . . C159 C 1.3787(4) 0.0979(4) 0.7692(5) 0.0400(15) Uani 1 1 d . . . . . H56 H 1.4138 0.0755 0.8240 0.048 Uiso 1 1 calc R U . . . C160 C 0.9432(4) 0.0721(4) 0.6350(4) 0.0365(15) Uani 1 1 d . . . . . H57 H 0.8872 0.0615 0.5933 0.044 Uiso 1 1 calc R U . . . C161 C 1.3672(5) 0.1578(5) 0.6376(5) 0.048(2) Uani 1 1 d . . . . . H58 H 1.3932 0.1784 0.6021 0.058 Uiso 1 1 calc R U . . . C162 C 0.5264(4) 0.5559(4) 0.7600(5) 0.0397(17) Uani 1 1 d . . . . . H59 H 0.5631 0.5301 0.7377 0.048 Uiso 1 1 calc R U . . . C163 C 0.6159(4) 0.1264(4) 0.6461(4) 0.0370(15) Uani 1 1 d . . . . . H60 H 0.5663 0.1175 0.5952 0.044 Uiso 1 1 calc R U . . . C164 C 0.7008(5) 0.0889(4) 0.7920(5) 0.0403(16) Uani 1 1 d . . . . . H61 H 0.7080 0.0555 0.8412 0.048 Uiso 1 1 calc R U . . . C165 C 1.3015(5) 0.4104(4) 0.7059(5) 0.0454(18) Uani 1 1 d . . . . . H62 H 1.3516 0.4419 0.7125 0.055 Uiso 1 1 calc R U . . . C166 C 1.2307(6) 0.4214(4) 0.6347(5) 0.051(2) Uani 1 1 d . . . . . H63 H 1.2316 0.4596 0.5914 0.061 Uiso 1 1 calc R U . . . C167 C 1.4160(5) 0.1304(5) 0.7166(5) 0.0456(18) Uani 1 1 d . . . . . H64 H 1.4762 0.1330 0.7371 0.055 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S5 0.0319(8) 0.0336(8) 0.0305(7) -0.0041(6) 0.0065(6) 0.0012(6) S1 0.0264(8) 0.0357(8) 0.0385(8) 0.0119(7) 0.0112(6) -0.0009(6) S6 0.0291(8) 0.0397(9) 0.0426(8) -0.0084(7) 0.0154(7) 0.0046(7) S3 0.0522(10) 0.0324(8) 0.0233(7) -0.0011(6) 0.0141(7) -0.0110(7) S4 0.0313(8) 0.0314(8) 0.0415(9) 0.0070(7) 0.0040(7) 0.0019(6) S7 0.0446(10) 0.0386(9) 0.0303(7) -0.0064(6) 0.0124(7) 0.0106(7) S2 0.0367(8) 0.0394(9) 0.0306(7) -0.0029(7) 0.0077(6) -0.0084(7) S8 0.0462(10) 0.0346(9) 0.0331(8) 0.0023(7) 0.0036(7) 0.0028(7) C48 0.030(3) 0.015(3) 0.029(3) 0.001(2) 0.018(2) 0.004(2) C49 0.029(3) 0.017(3) 0.025(3) 0.001(2) 0.016(2) -0.006(2) C50 0.032(3) 0.014(3) 0.026(3) 0.002(2) 0.014(2) 0.001(2) C51 0.034(3) 0.010(2) 0.026(3) -0.003(2) 0.016(2) -0.004(2) C52 0.031(3) 0.017(3) 0.023(3) 0.004(2) 0.015(2) -0.003(2) C53 0.026(3) 0.019(3) 0.027(3) 0.001(2) 0.014(2) -0.002(2) C54 0.034(3) 0.020(3) 0.027(3) -0.003(2) 0.019(2) -0.005(2) C55 0.033(3) 0.019(3) 0.031(3) 0.004(2) 0.021(2) -0.003(2) C56 0.031(3) 0.016(3) 0.034(3) 0.004(2) 0.019(3) 0.001(2) C57 0.030(3) 0.016(2) 0.026(3) 0.003(2) 0.014(2) 0.003(2) C58 0.039(3) 0.015(3) 0.039(3) -0.006(2) 0.025(3) -0.003(2) C59 0.029(3) 0.012(2) 0.026(3) 0.001(2) 0.014(2) 0.003(2) C60 0.032(3) 0.015(3) 0.025(3) 0.002(2) 0.017(2) -0.005(2) C61 0.030(3) 0.015(3) 0.028(3) 0.001(2) 0.011(2) 0.002(2) C62 0.037(4) 0.039(4) 0.030(3) 0.004(3) 0.010(3) -0.016(3) C63 0.024(3) 0.017(3) 0.038(3) -0.003(2) 0.017(2) 0.000(2) C64 0.033(3) 0.014(2) 0.023(3) 0.001(2) 0.012(2) -0.001(2) C65 0.034(3) 0.014(2) 0.028(3) 0.005(2) 0.018(2) 0.000(2) C66 0.024(3) 0.018(3) 0.028(3) -0.001(2) 0.015(2) -0.003(2) C67 0.038(3) 0.017(3) 0.034(3) 0.002(2) 0.022(3) 0.005(2) C68 0.054(4) 0.017(3) 0.031(3) -0.005(2) 0.030(3) -0.007(3) C69 0.040(3) 0.022(3) 0.024(3) 0.001(2) 0.016(3) 0.003(2) C70 0.031(3) 0.022(3) 0.027(3) 0.000(2) 0.012(2) -0.003(2) C71 0.030(3) 0.019(3) 0.023(3) 0.001(2) 0.014(2) -0.003(2) C72 0.039(3) 0.016(3) 0.034(3) -0.007(2) 0.022(3) -0.008(2) C73 0.025(3) 0.032(3) 0.034(3) -0.006(2) 0.017(3) 0.006(2) C74 0.033(3) 0.025(3) 0.028(3) 0.009(2) 0.016(3) -0.007(2) C75 0.031(3) 0.018(3) 0.034(3) -0.004(2) 0.019(3) 0.000(2) C76 0.030(3) 0.021(3) 0.024(3) -0.002(2) 0.016(2) 0.000(2) C77 0.037(3) 0.021(3) 0.028(3) 0.005(2) 0.015(3) -0.008(2) C78 0.034(3) 0.014(3) 0.035(3) 0.002(2) 0.016(3) 0.001(2) C79 0.037(3) 0.023(3) 0.030(3) -0.011(2) 0.024(3) -0.005(2) C80 0.036(3) 0.017(3) 0.026(3) -0.004(2) 0.014(2) -0.001(2) C81 0.068(5) 0.017(3) 0.061(4) -0.003(3) 0.055(4) -0.005(3) C82 0.033(3) 0.029(3) 0.028(3) -0.001(2) 0.014(2) 0.008(3) C83 0.033(3) 0.019(3) 0.032(3) -0.007(2) 0.016(3) -0.003(2) C84 0.023(3) 0.017(3) 0.030(3) 0.006(2) 0.013(2) 0.006(2) C85 0.040(4) 0.020(3) 0.033(3) 0.004(2) 0.022(3) 0.009(2) C86 0.032(3) 0.023(3) 0.026(3) 0.008(2) 0.018(2) 0.000(2) C87 0.033(3) 0.029(3) 0.033(3) -0.008(2) 0.016(3) 0.005(3) C88 0.034(3) 0.035(3) 0.025(3) 0.001(2) 0.013(3) 0.013(3) C89 0.036(3) 0.020(3) 0.031(3) -0.002(2) 0.015(3) -0.001(2) C90 0.050(4) 0.024(3) 0.044(4) -0.007(3) 0.036(3) -0.007(3) C91 0.063(4) 0.015(3) 0.053(4) -0.009(3) 0.045(4) -0.004(3) C92 0.030(3) 0.025(3) 0.034(3) 0.003(2) 0.011(3) -0.005(2) C93 0.051(4) 0.029(3) 0.028(3) -0.006(2) 0.021(3) -0.015(3) C94 0.035(3) 0.017(3) 0.051(4) 0.013(3) 0.027(3) 0.009(2) C95 0.034(3) 0.035(3) 0.033(3) 0.013(3) 0.012(3) -0.003(3) C96 0.033(3) 0.016(2) 0.026(3) -0.002(2) 0.015(2) -0.002(2) C97 0.032(3) 0.025(3) 0.037(3) 0.008(2) 0.013(3) 0.000(2) C98 0.029(3) 0.021(3) 0.040(3) 0.002(2) 0.009(3) 0.001(2) C99 0.053(4) 0.027(3) 0.039(3) 0.008(3) 0.035(3) 0.010(3) C100 0.046(4) 0.015(3) 0.043(3) 0.003(2) 0.031(3) 0.002(3) C101 0.040(3) 0.026(3) 0.031(3) 0.001(2) 0.015(3) -0.006(3) C102 0.034(3) 0.022(3) 0.055(4) 0.013(3) 0.031(3) 0.006(3) C103 0.037(3) 0.023(3) 0.039(3) -0.005(2) 0.023(3) 0.001(3) C104 0.025(3) 0.026(3) 0.034(3) 0.011(2) 0.017(2) 0.002(2) C105 0.059(4) 0.019(3) 0.028(3) 0.000(2) 0.026(3) -0.002(3) C106 0.027(3) 0.022(3) 0.026(3) -0.002(2) 0.015(2) -0.003(2) C107 0.038(3) 0.023(3) 0.026(3) 0.000(2) 0.008(2) -0.005(3) C108 0.034(3) 0.024(3) 0.025(3) -0.002(2) 0.018(3) 0.004(2) C109 0.035(3) 0.018(3) 0.030(3) -0.001(2) 0.007(3) -0.003(2) C110 0.030(3) 0.025(3) 0.042(3) 0.011(3) 0.017(3) 0.000(2) C111 0.039(4) 0.021(3) 0.052(4) 0.005(3) 0.032(3) 0.001(3) C112 0.049(4) 0.036(4) 0.032(3) 0.005(3) 0.015(3) 0.025(3) C113 0.048(4) 0.020(3) 0.055(4) -0.007(3) 0.039(4) -0.006(3) C114 0.033(3) 0.022(3) 0.033(3) -0.002(2) 0.018(3) -0.005(2) C115 0.034(3) 0.019(3) 0.034(3) -0.001(2) 0.019(3) -0.003(2) C116 0.043(4) 0.017(3) 0.055(4) 0.001(3) 0.032(3) 0.002(3) C117 0.061(5) 0.036(4) 0.038(4) 0.015(3) 0.028(3) 0.028(3) C118 0.054(4) 0.026(3) 0.025(3) -0.005(2) 0.017(3) -0.009(3) C119 0.046(4) 0.022(3) 0.036(3) -0.004(2) 0.027(3) -0.007(3) C120 0.036(3) 0.012(2) 0.028(3) 0.002(2) 0.017(3) 0.002(2) C121 0.051(4) 0.027(3) 0.024(3) -0.001(2) 0.012(3) -0.001(3) C122 0.033(4) 0.035(4) 0.071(5) -0.030(3) 0.032(4) -0.014(3) C123 0.036(3) 0.020(3) 0.045(4) 0.005(3) 0.021(3) 0.000(2) C124 0.049(4) 0.023(3) 0.019(3) 0.000(2) 0.006(3) -0.001(3) C125 0.042(4) 0.027(3) 0.053(4) -0.008(3) 0.034(3) -0.002(3) C126 0.061(5) 0.018(3) 0.078(5) 0.007(3) 0.056(5) 0.004(3) C127 0.042(4) 0.024(3) 0.031(3) -0.006(2) 0.023(3) -0.005(3) C128 0.057(4) 0.025(3) 0.035(3) 0.006(3) 0.031(3) 0.013(3) C129 0.050(4) 0.032(3) 0.029(3) 0.009(3) 0.021(3) 0.018(3) C130 0.039(4) 0.025(3) 0.059(4) -0.018(3) 0.036(3) -0.011(3) C131 0.054(4) 0.031(3) 0.024(3) -0.007(2) 0.024(3) -0.016(3) C132 0.039(4) 0.022(3) 0.047(4) 0.005(3) 0.031(3) 0.005(3) C133 0.031(3) 0.021(3) 0.030(3) 0.000(2) 0.020(3) 0.008(2) C134 0.034(3) 0.019(3) 0.051(4) -0.001(3) 0.027(3) -0.001(2) C135 0.056(4) 0.027(3) 0.042(3) 0.004(3) 0.039(3) 0.013(3) C136 0.037(3) 0.030(3) 0.030(3) -0.010(2) 0.019(3) -0.003(3) C137 0.057(4) 0.020(3) 0.031(3) 0.001(2) 0.025(3) 0.000(3) C138 0.031(3) 0.045(4) 0.053(4) -0.025(3) 0.019(3) -0.006(3) C139 0.068(5) 0.025(3) 0.038(3) -0.005(3) 0.039(4) -0.014(3) C140 0.072(5) 0.024(3) 0.050(4) -0.004(3) 0.049(4) -0.004(3) C141 0.055(4) 0.018(3) 0.031(3) -0.002(2) 0.028(3) -0.012(3) C142 0.028(3) 0.030(3) 0.068(5) 0.011(3) 0.028(3) 0.008(3) C143 0.033(4) 0.026(3) 0.057(4) 0.001(3) 0.027(3) -0.002(3) C144 0.037(3) 0.027(3) 0.029(3) -0.001(2) 0.018(3) 0.010(3) C145 0.028(3) 0.028(3) 0.043(3) -0.006(3) 0.018(3) -0.006(2) C146 0.040(4) 0.026(3) 0.048(4) -0.001(3) 0.030(3) -0.002(3) C147 0.051(4) 0.024(3) 0.051(4) 0.008(3) 0.039(4) 0.010(3) C148 0.053(4) 0.016(3) 0.033(3) 0.000(2) 0.023(3) -0.001(3) C149 0.030(3) 0.017(3) 0.062(4) 0.009(3) 0.023(3) 0.004(2) C150 0.081(6) 0.028(3) 0.034(3) 0.003(3) 0.033(4) 0.012(3) C151 0.067(5) 0.021(3) 0.042(4) 0.000(3) 0.037(3) -0.001(3) C152 0.042(4) 0.017(3) 0.043(3) 0.001(2) 0.028(3) 0.003(3) C153 0.042(4) 0.017(3) 0.042(3) -0.007(2) 0.029(3) -0.006(2) C154 0.022(3) 0.027(3) 0.045(4) -0.001(3) 0.009(3) -0.002(2) C155 0.029(3) 0.023(3) 0.052(4) 0.004(3) 0.015(3) 0.001(3) C156 0.051(4) 0.022(3) 0.052(4) 0.006(3) 0.039(3) 0.004(3) C157 0.069(5) 0.021(3) 0.040(4) -0.002(3) 0.041(4) -0.001(3) C158 0.025(3) 0.024(3) 0.073(5) 0.004(3) 0.020(3) 0.005(3) C159 0.038(4) 0.031(3) 0.057(4) -0.014(3) 0.025(3) -0.001(3) C160 0.028(3) 0.022(3) 0.054(4) 0.008(3) 0.011(3) 0.001(2) C161 0.067(5) 0.032(4) 0.078(5) -0.018(4) 0.063(5) -0.018(3) C162 0.043(4) 0.021(3) 0.073(5) -0.004(3) 0.041(4) 0.001(3) C163 0.040(4) 0.026(3) 0.055(4) -0.001(3) 0.030(3) -0.001(3) C164 0.065(5) 0.026(3) 0.052(4) 0.010(3) 0.046(4) 0.010(3) C165 0.060(5) 0.027(3) 0.074(5) -0.026(3) 0.052(4) -0.023(3) C166 0.095(6) 0.022(3) 0.070(5) -0.009(3) 0.069(5) -0.018(4) C167 0.044(4) 0.040(4) 0.068(5) -0.018(4) 0.039(4) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S5 C83 1.733(6) . ? S5 C89 1.744(6) . ? S1 C104 1.734(6) . ? S1 C74 1.736(6) . ? S6 C136 1.729(6) . ? S6 C88 1.738(7) . ? S3 C141 1.726(7) . ? S3 C77 1.754(6) . ? S4 C109 1.721(6) . ? S4 C155 1.738(7) . ? S7 C87 1.728(7) . ? S7 C144 1.737(6) . ? S2 C92 1.728(6) . ? S2 C107 1.743(6) . ? S8 C98 1.737(6) . ? S8 C148 1.740(7) . ? C48 C83 1.393(8) . ? C48 C59 1.430(7) . ? C48 C64 1.471(7) . ? C49 C74 1.384(8) . ? C49 C60 1.444(8) . ? C49 C86 1.461(8) . ? C50 C107 1.399(8) . ? C50 C71 1.433(8) . ? C50 C61 1.444(8) . ? C51 C64 1.426(8) . ? C51 C68 1.422(7) . ? C51 C76 1.456(8) . ? C52 C77 1.388(8) . ? C52 C66 1.441(7) . ? C52 C114 1.467(8) . ? C53 C97 1.365(8) . ? C53 C65 1.404(8) . ? C53 H1 0.9500 . ? C54 C55 1.398(8) . ? C54 C75 1.424(8) . ? C54 C61 1.447(8) . ? C55 C101 1.377(8) . ? C55 H2 0.9500 . ? C56 C132 1.409(8) . ? C56 C66 1.420(8) . ? C56 C110 1.428(8) . ? C57 C82 1.363(7) . ? C57 C59 1.422(8) . ? C57 H3 0.9500 . ? C58 C103 1.417(8) . ? C58 C91 1.417(8) . ? C58 C80 1.447(8) . ? C59 C67 1.428(8) . ? C60 C96 1.407(8) . ? C60 C72 1.435(8) . ? C61 C92 1.391(8) . ? C62 C93 1.345(10) . ? C62 C74 1.407(9) . ? C62 H4 0.9500 . ? C63 C155 1.391(8) . ? C63 C115 1.435(8) . ? C63 C120 1.473(8) . ? C64 C89 1.402(8) . ? C65 C120 1.429(8) . ? C65 C69 1.439(8) . ? C66 C106 1.413(8) . ? C67 C99 1.391(8) . ? C67 C116 1.413(9) . ? C68 C119 1.413(9) . ? C68 C105 1.407(9) . ? C69 C146 1.414(9) . ? C69 C137 1.422(8) . ? C70 C106 1.383(8) . ? C70 C127 1.402(8) . ? C70 H5 0.9500 . ? C71 C100 1.435(8) . ? C71 C86 1.441(8) . ? C72 C93 1.418(9) . ? C72 C113 1.435(9) . ? C73 C87 1.372(9) . ? C73 C133 1.445(8) . ? C73 C79 1.448(8) . ? C75 C90 1.407(8) . ? C75 C134 1.434(9) . ? C76 C136 1.403(8) . ? C76 C108 1.443(8) . ? C77 C95 1.397(9) . ? C78 C98 1.403(8) . ? C78 C84 1.441(8) . ? C78 C80 1.456(8) . ? C79 C153 1.396(9) . ? C79 C130 1.434(8) . ? C80 C148 1.390(8) . ? C81 C139 1.360(10) . ? C81 C111 1.424(9) . ? C81 H6 0.9500 . ? C82 C129 1.408(9) . ? C82 H7 0.9500 . ? C83 C145 1.404(8) . ? C84 C94 1.422(8) . ? C84 C133 1.451(8) . ? C85 C152 1.410(9) . ? C85 C108 1.428(8) . ? C85 C135 1.427(8) . ? C86 C104 1.390(8) . ? C87 C138 1.422(9) . ? C88 C108 1.408(8) . ? C88 C112 1.416(9) . ? C89 C124 1.393(8) . ? C90 C131 1.361(9) . ? C90 H8 0.9500 . ? C91 C161 1.411(10) . ? C91 C140 1.429(10) . ? C92 C154 1.430(9) . ? C93 H9 0.9500 . ? C94 C147 1.405(9) . ? C94 C149 1.430(9) . ? C95 C110 1.366(9) . ? C95 H10 0.9500 . ? C96 C123 1.377(8) . ? C96 H11 0.9500 . ? C97 C142 1.407(9) . ? C97 H12 0.9500 . ? C98 C160 1.400(9) . ? C99 C129 1.371(10) . ? C99 H13 0.9500 . ? C100 C157 1.409(9) . ? C100 C156 1.436(9) . ? C101 C131 1.405(9) . ? C101 H14 0.9500 . ? C102 C156 1.342(9) . ? C102 C104 1.415(8) . ? C102 H15 0.9500 . ? C103 C159 1.367(9) . ? C103 H16 0.9500 . ? C105 C124 1.378(9) . ? C105 H17 0.9500 . ? C106 H18 0.9500 . ? C107 C118 1.412(9) . ? C109 C120 1.388(8) . ? C109 C121 1.418(9) . ? C110 H19 0.9500 . ? C111 C162 1.409(10) . ? C111 C115 1.444(8) . ? C112 C117 1.340(11) . ? C112 H20 0.9500 . ? C113 C143 1.348(10) . ? C113 H21 0.9500 . ? C114 C141 1.403(8) . ? C114 C115 1.429(8) . ? C116 C145 1.358(9) . ? C116 H22 0.9500 . ? C117 C135 1.421(10) . ? C117 H23 0.9500 . ? C118 C157 1.356(10) . ? C118 H24 0.9500 . ? C119 C125 1.339(9) . ? C119 H25 0.9500 . ? C121 C137 1.355(10) . ? C121 H26 0.9500 . ? C122 C138 1.339(10) . ? C122 C130 1.434(10) . ? C122 H27 0.9500 . ? C123 C143 1.393(9) . ? C123 H28 0.9500 . ? C124 H29 0.9500 . ? C125 C136 1.414(8) . ? C125 H30 0.9500 . ? C126 C164 1.370(11) . ? C126 C163 1.401(9) . ? C126 H31 0.9500 . ? C127 C132 1.351(9) . ? C127 H32 0.9500 . ? C128 C144 1.400(9) . ? C128 C147 1.376(10) . ? C128 H33 0.9500 . ? C129 H34 0.9500 . ? C130 C165 1.401(10) . ? C131 H35 0.9500 . ? C132 H36 0.9500 . ? C133 C144 1.395(8) . ? C134 C154 1.356(9) . ? C134 H37 0.9500 . ? C135 C164 1.410(10) . ? C137 H38 0.9500 . ? C138 H39 0.9500 . ? C139 C141 1.404(9) . ? C139 H40 0.9500 . ? C140 C150 1.341(11) . ? C140 H41 0.9500 . ? C142 C146 1.357(10) . ? C142 H42 0.9500 . ? C143 H43 0.9500 . ? C145 H44 0.9500 . ? C146 H45 0.9500 . ? C147 H46 0.9500 . ? C148 C150 1.410(9) . ? C149 C160 1.340(10) . ? C149 H47 0.9500 . ? C150 H48 0.9500 . ? C151 C153 1.382(8) . ? C151 C166 1.405(10) . ? C151 H49 0.9500 . ? C152 C163 1.380(9) . ? C152 H50 0.9500 . ? C153 H51 0.9500 . ? C154 H52 0.9500 . ? C155 C158 1.416(9) . ? C156 H53 0.9500 . ? C157 H54 0.9500 . ? C158 C162 1.349(10) . ? C158 H55 0.9500 . ? C159 C167 1.403(10) . ? C159 H56 0.9500 . ? C160 H57 0.9500 . ? C161 C167 1.340(11) . ? C161 H58 0.9500 . ? C162 H59 0.9500 . ? C163 H60 0.9500 . ? C164 H61 0.9500 . ? C165 C166 1.337(11) . ? C165 H62 0.9500 . ? C166 H63 0.9500 . ? C167 H64 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C83 S5 C89 91.4(3) . . ? C104 S1 C74 91.1(3) . . ? C136 S6 C88 91.1(3) . . ? C141 S3 C77 91.5(3) . . ? C109 S4 C155 91.0(3) . . ? C87 S7 C144 90.6(3) . . ? C92 S2 C107 90.6(3) . . ? C98 S8 C148 91.3(3) . . ? C83 C48 C59 117.4(5) . . ? C83 C48 C64 111.5(5) . . ? C59 C48 C64 130.9(5) . . ? C74 C49 C60 117.4(5) . . ? C74 C49 C86 111.6(5) . . ? C60 C49 C86 130.8(5) . . ? C107 C50 C71 116.2(5) . . ? C107 C50 C61 111.0(5) . . ? C71 C50 C61 132.7(5) . . ? C64 C51 C68 117.4(5) . . ? C64 C51 C76 126.9(5) . . ? C68 C51 C76 115.8(5) . . ? C77 C52 C66 115.8(5) . . ? C77 C52 C114 112.3(5) . . ? C66 C52 C114 131.5(5) . . ? C97 C53 C65 121.9(5) . . ? C97 C53 H1 119.0 . . ? C65 C53 H1 119.0 . . ? C55 C54 C75 118.4(5) . . ? C55 C54 C61 123.3(5) . . ? C75 C54 C61 118.1(5) . . ? C101 C55 C54 121.1(5) . . ? C101 C55 H2 119.4 . . ? C54 C55 H2 119.4 . . ? C132 C56 C66 120.5(5) . . ? C132 C56 C110 119.5(5) . . ? C66 C56 C110 119.8(5) . . ? C82 C57 C59 121.1(5) . . ? C82 C57 H3 119.4 . . ? C59 C57 H3 119.4 . . ? C103 C58 C91 117.7(6) . . ? C103 C58 C80 123.2(5) . . ? C91 C58 C80 118.7(6) . . ? C67 C59 C57 117.2(5) . . ? C67 C59 C48 118.9(5) . . ? C57 C59 C48 123.6(5) . . ? C96 C60 C72 117.6(5) . . ? C96 C60 C49 124.3(5) . . ? C72 C60 C49 117.9(5) . . ? C92 C61 C50 111.4(5) . . ? C92 C61 C54 117.2(5) . . ? C50 C61 C54 131.2(5) . . ? C93 C62 C74 118.6(6) . . ? C93 C62 H4 120.7 . . ? C74 C62 H4 120.7 . . ? C155 C63 C115 118.0(5) . . ? C155 C63 C120 111.1(5) . . ? C115 C63 C120 130.9(5) . . ? C89 C64 C51 117.2(5) . . ? C89 C64 C48 110.7(5) . . ? C51 C64 C48 132.1(5) . . ? C53 C65 C120 124.6(5) . . ? C53 C65 C69 117.7(5) . . ? C120 C65 C69 117.6(5) . . ? C106 C66 C56 117.3(5) . . ? C106 C66 C52 123.4(5) . . ? C56 C66 C52 119.2(5) . . ? C99 C67 C116 120.9(6) . . ? C99 C67 C59 119.7(6) . . ? C116 C67 C59 119.2(5) . . ? C119 C68 C105 119.5(5) . . ? C119 C68 C51 120.9(6) . . ? C105 C68 C51 119.6(6) . . ? C146 C69 C137 121.6(6) . . ? C146 C69 C65 118.4(5) . . ? C137 C69 C65 119.7(6) . . ? C106 C70 C127 119.7(5) . . ? C106 C70 H5 120.1 . . ? C127 C70 H5 120.1 . . ? C50 C71 C100 117.0(5) . . ? C50 C71 C86 126.6(5) . . ? C100 C71 C86 116.3(5) . . ? C93 C72 C60 119.5(6) . . ? C93 C72 C113 121.7(5) . . ? C60 C72 C113 118.7(6) . . ? C87 C73 C133 111.1(5) . . ? C87 C73 C79 118.5(6) . . ? C133 C73 C79 130.3(5) . . ? C49 C74 C62 123.5(6) . . ? C49 C74 S1 112.6(4) . . ? C62 C74 S1 123.9(5) . . ? C90 C75 C54 118.9(6) . . ? C90 C75 C134 119.9(5) . . ? C54 C75 C134 121.0(5) . . ? C136 C76 C108 111.3(5) . . ? C136 C76 C51 117.0(5) . . ? C108 C76 C51 131.7(5) . . ? C95 C77 C52 124.7(5) . . ? C95 C77 S3 123.5(5) . . ? C52 C77 S3 111.8(4) . . ? C98 C78 C84 117.1(5) . . ? C98 C78 C80 110.7(5) . . ? C84 C78 C80 132.2(5) . . ? C153 C79 C130 117.9(6) . . ? C153 C79 C73 124.3(5) . . ? C130 C79 C73 117.6(6) . . ? C148 C80 C58 116.8(5) . . ? C148 C80 C78 112.0(5) . . ? C58 C80 C78 131.0(5) . . ? C139 C81 C111 121.9(6) . . ? C139 C81 H6 119.0 . . ? C111 C81 H6 119.0 . . ? C57 C82 C129 120.9(6) . . ? C57 C82 H7 119.6 . . ? C129 C82 H7 119.6 . . ? C48 C83 C145 122.5(5) . . ? C48 C83 S5 112.9(4) . . ? C145 C83 S5 124.6(5) . . ? C94 C84 C78 116.7(5) . . ? C94 C84 C133 117.1(5) . . ? C78 C84 C133 126.2(5) . . ? C152 C85 C108 123.8(5) . . ? C152 C85 C135 117.5(6) . . ? C108 C85 C135 118.6(6) . . ? C104 C86 C71 117.3(5) . . ? C104 C86 C49 110.9(5) . . ? C71 C86 C49 131.8(5) . . ? C73 C87 C138 122.6(6) . . ? C73 C87 S7 113.7(5) . . ? C138 C87 S7 123.7(5) . . ? C108 C88 C112 122.9(6) . . ? C108 C88 S6 112.5(4) . . ? C112 C88 S6 124.6(5) . . ? C124 C89 C64 123.6(6) . . ? C124 C89 S5 123.8(5) . . ? C64 C89 S5 112.5(4) . . ? C131 C90 C75 121.3(6) . . ? C131 C90 H8 119.3 . . ? C75 C90 H8 119.3 . . ? C161 C91 C140 121.4(6) . . ? C161 C91 C58 119.4(6) . . ? C140 C91 C58 119.1(6) . . ? C61 C92 C154 123.0(6) . . ? C61 C92 S2 113.2(5) . . ? C154 C92 S2 123.7(5) . . ? C62 C93 C72 121.9(6) . . ? C62 C93 H9 119.1 . . ? C72 C93 H9 119.1 . . ? C147 C94 C84 120.9(6) . . ? C147 C94 C149 119.0(6) . . ? C84 C94 C149 120.0(6) . . ? C110 C95 C77 118.3(6) . . ? C110 C95 H10 120.8 . . ? C77 C95 H10 120.8 . . ? C123 C96 C60 121.3(5) . . ? C123 C96 H11 119.4 . . ? C60 C96 H11 119.4 . . ? C53 C97 C142 120.2(6) . . ? C53 C97 H12 119.9 . . ? C142 C97 H12 119.9 . . ? C160 C98 C78 123.5(6) . . ? C160 C98 S8 124.0(5) . . ? C78 C98 S8 112.5(5) . . ? C129 C99 C67 121.6(6) . . ? C129 C99 H13 119.2 . . ? C67 C99 H13 119.2 . . ? C157 C100 C71 120.4(6) . . ? C157 C100 C156 119.6(5) . . ? C71 C100 C156 120.0(6) . . ? C55 C101 C131 120.2(6) . . ? C55 C101 H14 119.9 . . ? C131 C101 H14 119.9 . . ? C156 C102 C104 118.2(6) . . ? C156 C102 H15 120.9 . . ? C104 C102 H15 120.9 . . ? C159 C103 C58 120.5(6) . . ? C159 C103 H16 119.7 . . ? C58 C103 H16 119.7 . . ? C86 C104 C102 123.5(6) . . ? C86 C104 S1 112.8(4) . . ? C102 C104 S1 123.6(5) . . ? C124 C105 C68 121.9(5) . . ? C124 C105 H17 119.1 . . ? C68 C105 H17 119.1 . . ? C70 C106 C66 121.1(5) . . ? C70 C106 H18 119.5 . . ? C66 C106 H18 119.5 . . ? C50 C107 C118 124.3(6) . . ? C50 C107 S2 112.6(4) . . ? C118 C107 S2 123.1(5) . . ? C85 C108 C88 116.9(5) . . ? C85 C108 C76 131.6(5) . . ? C88 C108 C76 111.2(5) . . ? C120 C109 C121 122.1(6) . . ? C120 C109 S4 113.9(5) . . ? C121 C109 S4 123.9(5) . . ? C95 C110 C56 120.6(6) . . ? C95 C110 H19 119.7 . . ? C56 C110 H19 119.7 . . ? C162 C111 C81 120.3(6) . . ? C162 C111 C115 120.0(6) . . ? C81 C111 C115 119.7(6) . . ? C117 C112 C88 118.4(6) . . ? C117 C112 H20 120.8 . . ? C88 C112 H20 120.8 . . ? C143 C113 C72 121.0(6) . . ? C143 C113 H21 119.5 . . ? C72 C113 H21 119.5 . . ? C141 C114 C115 118.4(5) . . ? C141 C114 C52 110.2(5) . . ? C115 C114 C52 131.3(5) . . ? C114 C115 C63 127.9(5) . . ? C114 C115 C111 115.8(5) . . ? C63 C115 C111 116.3(5) . . ? C145 C116 C67 121.4(6) . . ? C145 C116 H22 119.3 . . ? C67 C116 H22 119.3 . . ? C112 C117 C135 121.8(6) . . ? C112 C117 H23 119.1 . . ? C135 C117 H23 119.1 . . ? C157 C118 C107 117.4(6) . . ? C157 C118 H24 121.3 . . ? C107 C118 H24 121.3 . . ? C125 C119 C68 122.0(6) . . ? C125 C119 H25 119.0 . . ? C68 C119 H25 119.0 . . ? C109 C120 C65 118.5(5) . . ? C109 C120 C63 110.4(5) . . ? C65 C120 C63 130.8(5) . . ? C137 C121 C109 118.7(5) . . ? C137 C121 H26 120.7 . . ? C109 C121 H26 120.7 . . ? C138 C122 C130 121.5(6) . . ? C138 C122 H27 119.2 . . ? C130 C122 H27 119.2 . . ? C96 C123 C143 120.9(6) . . ? C96 C123 H28 119.6 . . ? C143 C123 H28 119.6 . . ? C89 C124 C105 117.0(5) . . ? C89 C124 H29 121.5 . . ? C105 C124 H29 121.5 . . ? C119 C125 C136 117.7(6) . . ? C119 C125 H30 121.1 . . ? C136 C125 H30 121.1 . . ? C164 C126 C163 120.2(6) . . ? C164 C126 H31 119.9 . . ? C163 C126 H31 119.9 . . ? C132 C127 C70 121.1(5) . . ? C132 C127 H32 119.5 . . ? C70 C127 H32 119.5 . . ? C144 C128 C147 117.9(5) . . ? C144 C128 H33 121.1 . . ? C147 C128 H33 121.1 . . ? C99 C129 C82 119.0(5) . . ? C99 C129 H34 120.5 . . ? C82 C129 H34 120.5 . . ? C165 C130 C79 118.8(6) . . ? C165 C130 C122 121.7(6) . . ? C79 C130 C122 119.4(6) . . ? C90 C131 C101 119.7(5) . . ? C90 C131 H35 120.2 . . ? C101 C131 H35 120.2 . . ? C127 C132 C56 120.0(6) . . ? C127 C132 H36 120.0 . . ? C56 C132 H36 120.0 . . ? C144 C133 C73 111.5(5) . . ? C144 C133 C84 115.7(5) . . ? C73 C133 C84 132.8(5) . . ? C154 C134 C75 120.0(6) . . ? C154 C134 H37 120.0 . . ? C75 C134 H37 120.0 . . ? C164 C135 C117 121.2(6) . . ? C164 C135 C85 118.9(6) . . ? C117 C135 C85 119.8(6) . . ? C76 C136 C125 123.1(6) . . ? C76 C136 S6 112.8(4) . . ? C125 C136 S6 124.1(5) . . ? C121 C137 C69 121.4(6) . . ? C121 C137 H38 119.3 . . ? C69 C137 H38 119.3 . . ? C122 C138 C87 119.0(6) . . ? C122 C138 H39 120.5 . . ? C87 C138 H39 120.5 . . ? C81 C139 C141 117.6(6) . . ? C81 C139 H40 121.2 . . ? C141 C139 H40 121.2 . . ? C150 C140 C91 121.9(6) . . ? C150 C140 H41 119.1 . . ? C91 C140 H41 119.1 . . ? C114 C141 C139 123.0(6) . . ? C114 C141 S3 113.2(5) . . ? C139 C141 S3 123.9(5) . . ? C146 C142 C97 119.7(6) . . ? C146 C142 H42 120.2 . . ? C97 C142 H42 120.2 . . ? C113 C143 C123 120.3(6) . . ? C113 C143 H43 119.9 . . ? C123 C143 H43 119.9 . . ? C128 C144 C133 124.3(6) . . ? C128 C144 S7 123.5(5) . . ? C133 C144 S7 112.1(5) . . ? C116 C145 C83 119.0(6) . . ? C116 C145 H44 120.5 . . ? C83 C145 H44 120.5 . . ? C142 C146 C69 121.7(6) . . ? C142 C146 H45 119.1 . . ? C69 C146 H45 119.1 . . ? C128 C147 C94 120.4(6) . . ? C128 C147 H46 119.8 . . ? C94 C147 H46 119.8 . . ? C80 C148 C150 123.3(6) . . ? C80 C148 S8 112.3(5) . . ? C150 C148 S8 124.4(5) . . ? C160 C149 C94 121.5(6) . . ? C160 C149 H47 119.2 . . ? C94 C149 H47 119.2 . . ? C140 C150 C148 118.3(6) . . ? C140 C150 H48 120.8 . . ? C148 C150 H48 120.8 . . ? C153 C151 C166 119.2(7) . . ? C153 C151 H49 120.4 . . ? C166 C151 H49 120.4 . . ? C163 C152 C85 122.5(6) . . ? C163 C152 H50 118.7 . . ? C85 C152 H50 118.7 . . ? C151 C153 C79 121.3(6) . . ? C151 C153 H51 119.3 . . ? C79 C153 H51 119.3 . . ? C134 C154 C92 119.0(5) . . ? C134 C154 H52 120.5 . . ? C92 C154 H52 120.5 . . ? C63 C155 C158 122.3(6) . . ? C63 C155 S4 112.8(5) . . ? C158 C155 S4 124.8(5) . . ? C102 C156 C100 121.1(6) . . ? C102 C156 H53 119.5 . . ? C100 C156 H53 119.5 . . ? C118 C157 C100 121.3(6) . . ? C118 C157 H54 119.3 . . ? C100 C157 H54 119.3 . . ? C162 C158 C155 118.6(6) . . ? C162 C158 H55 120.7 . . ? C155 C158 H55 120.7 . . ? C103 C159 C167 120.6(7) . . ? C103 C159 H56 119.7 . . ? C167 C159 H56 119.7 . . ? C149 C160 C98 118.1(6) . . ? C149 C160 H57 120.9 . . ? C98 C160 H57 120.9 . . ? C167 C161 C91 121.0(6) . . ? C167 C161 H58 119.5 . . ? C91 C161 H58 119.5 . . ? C158 C162 C111 121.6(6) . . ? C158 C162 H59 119.2 . . ? C111 C162 H59 119.2 . . ? C152 C163 C126 119.1(7) . . ? C152 C163 H60 120.4 . . ? C126 C163 H60 120.4 . . ? C126 C164 C135 121.6(6) . . ? C126 C164 H61 119.2 . . ? C135 C164 H61 119.2 . . ? C166 C165 C130 121.4(6) . . ? C166 C165 H62 119.3 . . ? C130 C165 H62 119.3 . . ? C165 C166 C151 120.9(6) . . ? C165 C166 H63 119.6 . . ? C151 C166 H63 119.6 . . ? C161 C167 C159 120.3(7) . . ? C161 C167 H64 119.9 . . ? C159 C167 H64 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C75 C54 C55 C101 4.8(8) . . . . ? C61 C54 C55 C101 178.3(5) . . . . ? C82 C57 C59 C67 4.8(8) . . . . ? C82 C57 C59 C48 178.9(5) . . . . ? C83 C48 C59 C67 13.7(7) . . . . ? C64 C48 C59 C67 -171.5(5) . . . . ? C83 C48 C59 C57 -160.4(5) . . . . ? C64 C48 C59 C57 14.5(9) . . . . ? C74 C49 C60 C96 -162.4(5) . . . . ? C86 C49 C60 C96 11.9(9) . . . . ? C74 C49 C60 C72 13.0(7) . . . . ? C86 C49 C60 C72 -172.6(5) . . . . ? C107 C50 C61 C92 11.7(7) . . . . ? C71 C50 C61 C92 -166.8(6) . . . . ? C107 C50 C61 C54 -163.3(6) . . . . ? C71 C50 C61 C54 18.3(10) . . . . ? C55 C54 C61 C92 -159.9(5) . . . . ? C75 C54 C61 C92 13.7(8) . . . . ? C55 C54 C61 C50 14.8(9) . . . . ? C75 C54 C61 C50 -171.6(5) . . . . ? C68 C51 C64 C89 21.4(7) . . . . ? C76 C51 C64 C89 -159.2(5) . . . . ? C68 C51 C64 C48 -161.7(5) . . . . ? C76 C51 C64 C48 17.6(9) . . . . ? C83 C48 C64 C89 10.9(6) . . . . ? C59 C48 C64 C89 -164.2(5) . . . . ? C83 C48 C64 C51 -166.1(6) . . . . ? C59 C48 C64 C51 18.8(10) . . . . ? C97 C53 C65 C120 179.2(5) . . . . ? C97 C53 C65 C69 4.1(8) . . . . ? C132 C56 C66 C106 -5.4(8) . . . . ? C110 C56 C66 C106 170.2(5) . . . . ? C132 C56 C66 C52 177.9(5) . . . . ? C110 C56 C66 C52 -6.5(8) . . . . ? C77 C52 C66 C106 -162.8(5) . . . . ? C114 C52 C66 C106 9.9(9) . . . . ? C77 C52 C66 C56 13.6(7) . . . . ? C114 C52 C66 C56 -173.7(5) . . . . ? C57 C59 C67 C99 -7.1(8) . . . . ? C48 C59 C67 C99 178.5(5) . . . . ? C57 C59 C67 C116 168.8(5) . . . . ? C48 C59 C67 C116 -5.6(8) . . . . ? C64 C51 C68 C119 163.7(5) . . . . ? C76 C51 C68 C119 -15.8(7) . . . . ? C64 C51 C68 C105 -16.5(8) . . . . ? C76 C51 C68 C105 164.1(5) . . . . ? C53 C65 C69 C146 -6.1(8) . . . . ? C120 C65 C69 C146 178.4(5) . . . . ? C53 C65 C69 C137 168.4(5) . . . . ? C120 C65 C69 C137 -7.1(8) . . . . ? C107 C50 C71 C100 21.2(7) . . . . ? C61 C50 C71 C100 -160.4(5) . . . . ? C107 C50 C71 C86 -159.9(5) . . . . ? C61 C50 C71 C86 18.5(10) . . . . ? C96 C60 C72 C93 168.4(5) . . . . ? C49 C60 C72 C93 -7.3(8) . . . . ? C96 C60 C72 C113 -6.6(8) . . . . ? C49 C60 C72 C113 177.6(5) . . . . ? C60 C49 C74 C62 -10.8(8) . . . . ? C86 C49 C74 C62 173.7(5) . . . . ? C60 C49 C74 S1 167.0(4) . . . . ? C86 C49 C74 S1 -8.4(6) . . . . ? C93 C62 C74 C49 2.2(9) . . . . ? C93 C62 C74 S1 -175.4(5) . . . . ? C104 S1 C74 C49 2.8(4) . . . . ? C104 S1 C74 C62 -179.3(5) . . . . ? C55 C54 C75 C90 -7.4(8) . . . . ? C61 C54 C75 C90 178.7(5) . . . . ? C55 C54 C75 C134 168.2(5) . . . . ? C61 C54 C75 C134 -5.7(8) . . . . ? C64 C51 C76 C136 -157.6(5) . . . . ? C68 C51 C76 C136 21.8(7) . . . . ? C64 C51 C76 C108 19.0(9) . . . . ? C68 C51 C76 C108 -161.6(5) . . . . ? C66 C52 C77 C95 -13.7(8) . . . . ? C114 C52 C77 C95 172.2(5) . . . . ? C66 C52 C77 S3 166.5(4) . . . . ? C114 C52 C77 S3 -7.6(6) . . . . ? C141 S3 C77 C95 -178.0(5) . . . . ? C141 S3 C77 C52 1.8(4) . . . . ? C87 C73 C79 C153 -161.5(5) . . . . ? C133 C73 C79 C153 13.3(9) . . . . ? C87 C73 C79 C130 12.9(8) . . . . ? C133 C73 C79 C130 -172.3(5) . . . . ? C103 C58 C80 C148 -159.3(5) . . . . ? C91 C58 C80 C148 13.9(8) . . . . ? C103 C58 C80 C78 15.0(9) . . . . ? C91 C58 C80 C78 -171.8(6) . . . . ? C98 C78 C80 C148 11.9(7) . . . . ? C84 C78 C80 C148 -167.4(6) . . . . ? C98 C78 C80 C58 -162.6(6) . . . . ? C84 C78 C80 C58 18.2(10) . . . . ? C59 C57 C82 C129 0.9(9) . . . . ? C59 C48 C83 C145 -12.4(8) . . . . ? C64 C48 C83 C145 171.7(5) . . . . ? C59 C48 C83 S5 167.8(4) . . . . ? C64 C48 C83 S5 -8.0(6) . . . . ? C89 S5 C83 C48 2.5(4) . . . . ? C89 S5 C83 C145 -177.3(5) . . . . ? C98 C78 C84 C94 19.9(7) . . . . ? C80 C78 C84 C94 -160.9(6) . . . . ? C98 C78 C84 C133 -159.7(5) . . . . ? C80 C78 C84 C133 19.5(10) . . . . ? C50 C71 C86 C104 -157.3(5) . . . . ? C100 C71 C86 C104 21.6(7) . . . . ? C50 C71 C86 C49 20.8(9) . . . . ? C100 C71 C86 C49 -160.2(5) . . . . ? C74 C49 C86 C104 11.2(6) . . . . ? C60 C49 C86 C104 -163.5(5) . . . . ? C74 C49 C86 C71 -167.1(5) . . . . ? C60 C49 C86 C71 18.3(10) . . . . ? C133 C73 C87 C138 172.8(5) . . . . ? C79 C73 C87 C138 -11.4(9) . . . . ? C133 C73 C87 S7 -8.9(6) . . . . ? C79 C73 C87 S7 166.9(4) . . . . ? C144 S7 C87 C73 3.3(5) . . . . ? C144 S7 C87 C138 -178.4(5) . . . . ? C136 S6 C88 C108 2.1(5) . . . . ? C136 S6 C88 C112 -177.4(5) . . . . ? C51 C64 C89 C124 -13.1(8) . . . . ? C48 C64 C89 C124 169.4(5) . . . . ? C51 C64 C89 S5 168.4(4) . . . . ? C48 C64 C89 S5 -9.1(6) . . . . ? C83 S5 C89 C124 -174.4(5) . . . . ? C83 S5 C89 C64 4.0(4) . . . . ? C54 C75 C90 C131 5.2(8) . . . . ? C134 C75 C90 C131 -170.5(5) . . . . ? C103 C58 C91 C161 -7.8(8) . . . . ? C80 C58 C91 C161 178.6(5) . . . . ? C103 C58 C91 C140 169.0(5) . . . . ? C80 C58 C91 C140 -4.6(8) . . . . ? C50 C61 C92 C154 171.4(5) . . . . ? C54 C61 C92 C154 -12.9(8) . . . . ? C50 C61 C92 S2 -8.9(6) . . . . ? C54 C61 C92 S2 166.8(4) . . . . ? C107 S2 C92 C61 3.1(5) . . . . ? C107 S2 C92 C154 -177.3(5) . . . . ? C74 C62 C93 C72 4.2(9) . . . . ? C60 C72 C93 C62 -1.5(9) . . . . ? C113 C72 C93 C62 173.4(6) . . . . ? C78 C84 C94 C147 163.6(5) . . . . ? C133 C84 C94 C147 -16.8(8) . . . . ? C78 C84 C94 C149 -15.7(8) . . . . ? C133 C84 C94 C149 163.9(5) . . . . ? C52 C77 C95 C110 5.6(9) . . . . ? S3 C77 C95 C110 -174.6(4) . . . . ? C72 C60 C96 C123 3.9(8) . . . . ? C49 C60 C96 C123 179.4(5) . . . . ? C65 C53 C97 C142 1.1(8) . . . . ? C84 C78 C98 C160 -11.4(8) . . . . ? C80 C78 C98 C160 169.2(6) . . . . ? C84 C78 C98 S8 169.1(4) . . . . ? C80 C78 C98 S8 -10.3(6) . . . . ? C148 S8 C98 C160 -174.5(5) . . . . ? C148 S8 C98 C78 5.0(5) . . . . ? C116 C67 C99 C129 -172.0(5) . . . . ? C59 C67 C99 C129 3.8(9) . . . . ? C50 C71 C100 C157 -16.7(8) . . . . ? C86 C71 C100 C157 164.3(5) . . . . ? C50 C71 C100 C156 162.2(5) . . . . ? C86 C71 C100 C156 -16.9(8) . . . . ? C54 C55 C101 C131 0.2(9) . . . . ? C91 C58 C103 C159 5.9(8) . . . . ? C80 C58 C103 C159 179.1(5) . . . . ? C71 C86 C104 C102 -12.7(8) . . . . ? C49 C86 C104 C102 168.8(5) . . . . ? C71 C86 C104 S1 169.5(4) . . . . ? C49 C86 C104 S1 -9.1(6) . . . . ? C156 C102 C104 C86 -2.6(8) . . . . ? C156 C102 C104 S1 175.0(4) . . . . ? C74 S1 C104 C86 3.8(4) . . . . ? C74 S1 C104 C102 -174.1(5) . . . . ? C119 C68 C105 C124 -178.0(5) . . . . ? C51 C68 C105 C124 2.1(8) . . . . ? C127 C70 C106 C66 2.4(8) . . . . ? C56 C66 C106 C70 1.8(8) . . . . ? C52 C66 C106 C70 178.3(5) . . . . ? C71 C50 C107 C118 -12.8(8) . . . . ? C61 C50 C107 C118 168.5(5) . . . . ? C71 C50 C107 S2 169.3(4) . . . . ? C61 C50 C107 S2 -9.5(6) . . . . ? C92 S2 C107 C50 3.8(5) . . . . ? C92 S2 C107 C118 -174.1(5) . . . . ? C152 C85 C108 C88 -161.5(5) . . . . ? C135 C85 C108 C88 13.8(8) . . . . ? C152 C85 C108 C76 11.3(10) . . . . ? C135 C85 C108 C76 -173.4(5) . . . . ? C112 C88 C108 C85 -14.3(8) . . . . ? S6 C88 C108 C85 166.3(4) . . . . ? C112 C88 C108 C76 171.5(5) . . . . ? S6 C88 C108 C76 -8.0(6) . . . . ? C136 C76 C108 C85 -161.8(6) . . . . ? C51 C76 C108 C85 21.5(10) . . . . ? C136 C76 C108 C88 11.4(6) . . . . ? C51 C76 C108 C88 -165.3(5) . . . . ? C155 S4 C109 C120 2.3(5) . . . . ? C155 S4 C109 C121 -175.7(5) . . . . ? C77 C95 C110 C56 2.7(8) . . . . ? C132 C56 C110 C95 173.6(5) . . . . ? C66 C56 C110 C95 -2.0(8) . . . . ? C139 C81 C111 C162 -179.6(6) . . . . ? C139 C81 C111 C115 1.7(9) . . . . ? C108 C88 C112 C117 5.1(9) . . . . ? S6 C88 C112 C117 -175.5(5) . . . . ? C93 C72 C113 C143 -170.1(6) . . . . ? C60 C72 C113 C143 4.8(8) . . . . ? C77 C52 C114 C141 11.0(7) . . . . ? C66 C52 C114 C141 -161.9(5) . . . . ? C77 C52 C114 C115 -166.3(6) . . . . ? C66 C52 C114 C115 20.8(10) . . . . ? C141 C114 C115 C63 -157.8(6) . . . . ? C52 C114 C115 C63 19.4(10) . . . . ? C141 C114 C115 C111 22.1(8) . . . . ? C52 C114 C115 C111 -160.7(6) . . . . ? C155 C63 C115 C114 -158.8(6) . . . . ? C120 C63 C115 C114 17.8(10) . . . . ? C155 C63 C115 C111 21.3(8) . . . . ? C120 C63 C115 C111 -162.0(6) . . . . ? C162 C111 C115 C114 164.4(5) . . . . ? C81 C111 C115 C114 -16.9(8) . . . . ? C162 C111 C115 C63 -15.7(8) . . . . ? C81 C111 C115 C63 163.0(5) . . . . ? C99 C67 C116 C145 171.3(6) . . . . ? C59 C67 C116 C145 -4.6(8) . . . . ? C88 C112 C117 C135 4.5(9) . . . . ? C50 C107 C118 C157 -1.6(9) . . . . ? S2 C107 C118 C157 176.1(5) . . . . ? C105 C68 C119 C125 -179.4(6) . . . . ? C51 C68 C119 C125 0.4(9) . . . . ? C121 C109 C120 C65 -15.2(8) . . . . ? S4 C109 C120 C65 166.8(4) . . . . ? C121 C109 C120 C63 170.7(5) . . . . ? S4 C109 C120 C63 -7.3(6) . . . . ? C53 C65 C120 C109 -159.3(5) . . . . ? C69 C65 C120 C109 15.8(7) . . . . ? C53 C65 C120 C63 13.3(9) . . . . ? C69 C65 C120 C63 -171.6(5) . . . . ? C155 C63 C120 C109 9.9(7) . . . . ? C115 C63 C120 C109 -166.9(6) . . . . ? C155 C63 C120 C65 -163.2(6) . . . . ? C115 C63 C120 C65 20.0(10) . . . . ? C120 C109 C121 C137 5.1(9) . . . . ? S4 C109 C121 C137 -177.2(5) . . . . ? C60 C96 C123 C143 0.8(9) . . . . ? C64 C89 C124 C105 -1.2(9) . . . . ? S5 C89 C124 C105 177.1(4) . . . . ? C68 C105 C124 C89 6.8(8) . . . . ? C68 C119 C125 C136 8.5(9) . . . . ? C106 C70 C127 C132 -3.3(9) . . . . ? C67 C99 C129 C82 2.0(9) . . . . ? C57 C82 C129 C99 -4.5(9) . . . . ? C153 C79 C130 C165 -8.1(8) . . . . ? C73 C79 C130 C165 177.1(5) . . . . ? C153 C79 C130 C122 169.2(5) . . . . ? C73 C79 C130 C122 -5.6(8) . . . . ? C138 C122 C130 C165 173.3(6) . . . . ? C138 C122 C130 C79 -4.0(9) . . . . ? C75 C90 C131 C101 -0.2(9) . . . . ? C55 C101 C131 C90 -2.6(9) . . . . ? C70 C127 C132 C56 -0.3(9) . . . . ? C66 C56 C132 C127 4.7(8) . . . . ? C110 C56 C132 C127 -170.9(5) . . . . ? C87 C73 C133 C144 11.3(7) . . . . ? C79 C73 C133 C144 -163.8(6) . . . . ? C87 C73 C133 C84 -165.8(6) . . . . ? C79 C73 C133 C84 19.1(10) . . . . ? C94 C84 C133 C144 22.0(7) . . . . ? C78 C84 C133 C144 -158.4(5) . . . . ? C94 C84 C133 C73 -161.0(6) . . . . ? C78 C84 C133 C73 18.6(9) . . . . ? C90 C75 C134 C154 171.4(5) . . . . ? C54 C75 C134 C154 -4.2(8) . . . . ? C112 C117 C135 C164 171.6(6) . . . . ? C112 C117 C135 C85 -4.4(9) . . . . ? C152 C85 C135 C164 -5.6(8) . . . . ? C108 C85 C135 C164 178.8(5) . . . . ? C152 C85 C135 C117 170.5(5) . . . . ? C108 C85 C135 C117 -5.1(8) . . . . ? C108 C76 C136 C125 168.6(5) . . . . ? C51 C76 C136 C125 -14.1(8) . . . . ? C108 C76 C136 S6 -9.9(6) . . . . ? C51 C76 C136 S6 167.3(4) . . . . ? C119 C125 C136 C76 -1.3(9) . . . . ? C119 C125 C136 S6 177.1(5) . . . . ? C88 S6 C136 C76 4.6(5) . . . . ? C88 S6 C136 C125 -173.9(5) . . . . ? C109 C121 C137 C69 4.2(9) . . . . ? C146 C69 C137 C121 171.3(6) . . . . ? C65 C69 C137 C121 -3.0(9) . . . . ? C130 C122 C138 C87 6.0(9) . . . . ? C73 C87 C138 C122 1.8(9) . . . . ? S7 C87 C138 C122 -176.3(5) . . . . ? C111 C81 C139 C141 8.2(9) . . . . ? C161 C91 C140 C150 169.6(6) . . . . ? C58 C91 C140 C150 -7.1(9) . . . . ? C115 C114 C141 C139 -13.1(8) . . . . ? C52 C114 C141 C139 169.1(5) . . . . ? C115 C114 C141 S3 168.1(4) . . . . ? C52 C114 C141 S3 -9.7(6) . . . . ? C81 C139 C141 C114 -2.5(9) . . . . ? C81 C139 C141 S3 176.1(5) . . . . ? C77 S3 C141 C114 4.8(5) . . . . ? C77 S3 C141 C139 -174.0(5) . . . . ? C53 C97 C142 C146 -4.3(9) . . . . ? C72 C113 C143 C123 -0.1(9) . . . . ? C96 C123 C143 C113 -2.8(9) . . . . ? C147 C128 C144 C133 -1.7(9) . . . . ? C147 C128 C144 S7 175.8(5) . . . . ? C73 C133 C144 C128 168.8(5) . . . . ? C84 C133 C144 C128 -13.5(8) . . . . ? C73 C133 C144 S7 -8.9(6) . . . . ? C84 C133 C144 S7 168.7(4) . . . . ? C87 S7 C144 C128 -174.4(5) . . . . ? C87 S7 C144 C133 3.4(5) . . . . ? C67 C116 C145 C83 6.3(9) . . . . ? C48 C83 C145 C116 2.5(9) . . . . ? S5 C83 C145 C116 -177.8(5) . . . . ? C97 C142 C146 C69 2.1(9) . . . . ? C137 C69 C146 C142 -171.2(6) . . . . ? C65 C69 C146 C142 3.1(9) . . . . ? C144 C128 C147 C94 8.1(8) . . . . ? C84 C94 C147 C128 1.4(9) . . . . ? C149 C94 C147 C128 -179.3(5) . . . . ? C58 C80 C148 C150 -12.9(8) . . . . ? C78 C80 C148 C150 171.8(5) . . . . ? C58 C80 C148 S8 167.1(4) . . . . ? C78 C80 C148 S8 -8.2(6) . . . . ? C98 S8 C148 C80 2.0(5) . . . . ? C98 S8 C148 C150 -178.0(6) . . . . ? C147 C94 C149 C160 -177.5(6) . . . . ? C84 C94 C149 C160 1.8(9) . . . . ? C91 C140 C150 C148 8.7(9) . . . . ? C80 C148 C150 C140 1.7(9) . . . . ? S8 C148 C150 C140 -178.3(5) . . . . ? C108 C85 C152 C163 179.0(5) . . . . ? C135 C85 C152 C163 3.6(8) . . . . ? C166 C151 C153 C79 -0.9(9) . . . . ? C130 C79 C153 C151 6.4(8) . . . . ? C73 C79 C153 C151 -179.2(5) . . . . ? C75 C134 C154 C92 5.5(9) . . . . ? C61 C92 C154 C134 3.2(9) . . . . ? S2 C92 C154 C134 -176.4(5) . . . . ? C115 C63 C155 C158 -13.8(9) . . . . ? C120 C63 C155 C158 168.9(5) . . . . ? C115 C63 C155 S4 168.9(4) . . . . ? C120 C63 C155 S4 -8.4(6) . . . . ? C109 S4 C155 C63 3.8(5) . . . . ? C109 S4 C155 C158 -173.5(6) . . . . ? C104 C102 C156 C100 8.1(8) . . . . ? C157 C100 C156 C102 -179.2(6) . . . . ? C71 C100 C156 C102 1.9(8) . . . . ? C107 C118 C157 C100 7.1(9) . . . . ? C71 C100 C157 C118 2.1(9) . . . . ? C156 C100 C157 C118 -176.7(6) . . . . ? C63 C155 C158 C162 -0.7(9) . . . . ? S4 C155 C158 C162 176.3(5) . . . . ? C58 C103 C159 C167 -0.3(9) . . . . ? C94 C149 C160 C98 7.5(9) . . . . ? C78 C98 C160 C149 -2.5(9) . . . . ? S8 C98 C160 C149 176.9(5) . . . . ? C140 C91 C161 C167 -172.4(6) . . . . ? C58 C91 C161 C167 4.3(9) . . . . ? C155 C158 C162 C111 6.9(10) . . . . ? C81 C111 C162 C158 -177.2(6) . . . . ? C115 C111 C162 C158 1.6(9) . . . . ? C85 C152 C163 C126 0.6(9) . . . . ? C164 C126 C163 C152 -2.8(9) . . . . ? C163 C126 C164 C135 0.6(9) . . . . ? C117 C135 C164 C126 -172.4(6) . . . . ? C85 C135 C164 C126 3.7(9) . . . . ? C79 C130 C165 C166 4.5(9) . . . . ? C122 C130 C165 C166 -172.8(6) . . . . ? C130 C165 C166 C151 1.2(10) . . . . ? C153 C151 C166 C165 -3.1(9) . . . . ? C91 C161 C167 C159 1.4(10) . . . . ? C103 C159 C167 C161 -3.5(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C124 H29 S1 0.95 2.98 3.440(6) 111.1 2_546 C160 H57 S3 0.95 3.00 3.537(6) 117.2 2_646 _refine_diff_density_max 0.365 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.066 _shelx_res_file ; 91119yuk.res created by SHELXL-2014/7 TITL 91119yuk_a.res in P2(1) REM Yadorkari-X generated CELL 1.54187 17.2720 14.9852 17.3110 90.0000 114.5110 90.0000 ZERR 2.0 0.0020 0.0013 0.0020 0.0000 0.0030 0.0000 LATT -1 SYMM -X, 1/2+Y, -Z REM SPGR P21 monoclinic SFAC C H S UNIT 240 128 16 SIZE 0.11 0.10 0.01 TEMP -180.0 L.S. 50 FMAP 2 PLAN -20 ACTA CONF HTAB LIST 4 BOND $H OMIT 0 0 1 EQIV $1 -X, -1/2+Y, 1-Z EQIV $2 1-X, -1/2+Y, 1-Z HTAB C124 S1_$1 HTAB C160 S3_$2 WGHT 0.052000 6.954700 FVAR 1.16699 S5 3 0.501662 0.398248 0.498270 11.00000 0.03194 0.03360 = 0.03053 -0.00407 0.00649 0.00116 S1 3 -0.476753 0.792961 0.688711 11.00000 0.02641 0.03568 = 0.03849 0.01186 0.01117 -0.00093 S6 3 0.977234 0.310779 0.780065 11.00000 0.02910 0.03965 = 0.04264 -0.00840 0.01543 0.00464 S3 3 0.198935 0.711250 0.526766 11.00000 0.05218 0.03240 = 0.02335 -0.00110 0.01414 -0.01098 S4 3 0.513769 0.594369 0.984098 11.00000 0.03127 0.03143 = 0.04150 0.00699 0.00404 0.00187 S7 3 1.288896 0.187285 0.981093 11.00000 0.04460 0.03859 = 0.03026 -0.00641 0.01241 0.01057 S2 3 -0.022050 0.896247 1.020016 11.00000 0.03666 0.03938 = 0.03065 -0.00294 0.00774 -0.00837 S8 3 0.994600 0.115192 0.507593 11.00000 0.04619 0.03464 = 0.03310 0.00226 0.00363 0.00278 C48 1 0.625178 0.375087 0.648354 11.00000 0.03011 0.01469 = 0.02861 0.00108 0.01841 0.00445 C49 1 -0.316403 0.750151 0.761525 11.00000 0.02881 0.01743 = 0.02500 0.00091 0.01589 -0.00630 C50 1 -0.180524 0.879717 0.909553 11.00000 0.03241 0.01394 = 0.02584 0.00210 0.01385 0.00075 C51 1 0.752368 0.378120 0.600763 11.00000 0.03421 0.00995 = 0.02554 -0.00349 0.01623 -0.00381 C52 1 0.267480 0.749366 0.688413 11.00000 0.03089 0.01680 = 0.02271 0.00394 0.01463 -0.00298 C53 1 0.208784 0.604442 0.764008 11.00000 0.02571 0.01853 = 0.02707 0.00069 0.01437 -0.00183 AFIX 43 H1 2 0.228700 0.585032 0.723237 11.00000 -1.20000 AFIX 0 C54 1 -0.151612 0.868757 0.772065 11.00000 0.03397 0.01979 = 0.02744 -0.00297 0.01879 -0.00462 C55 1 -0.231008 0.895967 0.711396 11.00000 0.03251 0.01896 = 0.03073 0.00350 0.02077 -0.00337 AFIX 43 H2 2 -0.273320 0.915353 0.729301 11.00000 -1.20000 AFIX 0 C56 1 0.212808 0.862628 0.756651 11.00000 0.03104 0.01584 = 0.03422 0.00369 0.01919 0.00141 C57 1 0.743948 0.401101 0.792146 11.00000 0.03006 0.01557 = 0.02645 0.00267 0.01433 0.00277 AFIX 43 H3 2 0.779862 0.422870 0.767092 11.00000 -1.20000 AFIX 0 C58 1 1.238907 0.131590 0.660835 11.00000 0.03899 0.01454 = 0.03908 -0.00564 0.02516 -0.00319 C59 1 0.660194 0.372164 0.739067 11.00000 0.02912 0.01173 = 0.02585 0.00067 0.01376 0.00294 C60 1 -0.244815 0.692135 0.776675 11.00000 0.03240 0.01477 = 0.02534 0.00220 0.01684 -0.00547 C61 1 -0.128835 0.870544 0.862471 11.00000 0.02964 0.01517 = 0.02823 0.00101 0.01085 0.00178 C62 1 -0.392742 0.679245 0.622257 11.00000 0.03713 0.03868 = 0.02972 0.00417 0.00961 -0.01561 AFIX 43 H4 2 -0.443728 0.673052 0.572161 11.00000 -1.20000 AFIX 0 C63 1 0.410531 0.614601 0.824337 11.00000 0.02442 0.01703 = 0.03764 -0.00272 0.01689 0.00016 C64 1 0.666277 0.387693 0.589806 11.00000 0.03331 0.01400 = 0.02310 0.00099 0.01183 -0.00108 C65 1 0.268244 0.628524 0.845467 11.00000 0.03425 0.01397 = 0.02843 0.00548 0.01813 0.00044 C66 1 0.280417 0.806838 0.759462 11.00000 0.02389 0.01839 = 0.02772 -0.00101 0.01547 -0.00296 C67 1 0.606528 0.346685 0.779627 11.00000 0.03803 0.01669 = 0.03357 0.00162 0.02190 0.00544 C68 1 0.775989 0.420175 0.540116 11.00000 0.05377 0.01726 = 0.03121 -0.00466 0.03010 -0.00689 C69 1 0.236286 0.651830 0.907470 11.00000 0.03963 0.02170 = 0.02440 0.00134 0.01606 0.00286 C70 1 0.368683 0.872535 0.896597 11.00000 0.03147 0.02186 = 0.02670 0.00026 0.01200 -0.00336 AFIX 43 H5 2 0.422509 0.878796 0.943260 11.00000 -1.20000 AFIX 0 C71 1 -0.269673 0.867923 0.886752 11.00000 0.02997 0.01873 = 0.02346 0.00118 0.01378 -0.00292 C72 1 -0.246989 0.637292 0.707863 11.00000 0.03866 0.01583 = 0.03377 -0.00666 0.02165 -0.00849 C73 1 1.234339 0.239843 0.824066 11.00000 0.02532 0.03212 = 0.03416 -0.00563 0.01745 0.00593 C74 1 -0.389383 0.736072 0.688276 11.00000 0.03302 0.02475 = 0.02807 0.00865 0.01608 -0.00671 C75 1 -0.087136 0.846612 0.744237 11.00000 0.03149 0.01800 = 0.03411 -0.00360 0.01873 -0.00046 C76 1 0.819918 0.330121 0.668529 11.00000 0.03019 0.02114 = 0.02379 -0.00239 0.01612 -0.00049 C77 1 0.195768 0.767056 0.614498 11.00000 0.03686 0.02118 = 0.02786 0.00455 0.01522 -0.00763 C78 1 1.090596 0.120933 0.670727 11.00000 0.03372 0.01391 = 0.03462 0.00244 0.01646 0.00150 C79 1 1.229212 0.301246 0.757527 11.00000 0.03749 0.02268 = 0.03045 -0.01139 0.02352 -0.00492 C80 1 1.147018 0.132556 0.628137 11.00000 0.03599 0.01702 = 0.02560 -0.00362 0.01375 -0.00064 C81 1 0.418974 0.578337 0.614176 11.00000 0.06830 0.01716 = 0.06099 -0.00292 0.05493 -0.00504 AFIX 43 H6 2 0.455558 0.549577 0.593420 11.00000 -1.20000 AFIX 0 C82 1 0.773557 0.398131 0.878336 11.00000 0.03346 0.02912 = 0.02803 -0.00088 0.01379 0.00763 AFIX 43 H7 2 0.829451 0.418666 0.912468 11.00000 -1.20000 AFIX 0 C83 1 0.536904 0.371929 0.604959 11.00000 0.03285 0.01919 = 0.03176 -0.00745 0.01567 -0.00299 C84 1 1.104691 0.127145 0.758611 11.00000 0.02257 0.01686 = 0.02992 0.00584 0.01267 0.00554 C85 1 0.752243 0.201523 0.722542 11.00000 0.04046 0.01953 = 0.03344 0.00352 0.02207 0.00882 C86 1 -0.328969 0.819471 0.814542 11.00000 0.03160 0.02324 = 0.02611 0.00804 0.01775 0.00049 C87 1 1.301780 0.247144 0.901880 11.00000 0.03290 0.02923 = 0.03350 -0.00769 0.01588 0.00481 C88 1 0.897964 0.251166 0.794544 11.00000 0.03450 0.03461 = 0.02497 0.00057 0.01317 0.01262 C89 1 0.605914 0.409520 0.508284 11.00000 0.03578 0.01972 = 0.03095 -0.00199 0.01452 -0.00102 C90 1 -0.108450 0.842703 0.656522 11.00000 0.04969 0.02446 = 0.04396 -0.00721 0.03568 -0.00704 AFIX 43 H8 2 -0.067032 0.823134 0.637460 11.00000 -1.20000 AFIX 0 C91 1 1.277604 0.156484 0.606103 11.00000 0.06278 0.01455 = 0.05305 -0.00902 0.04499 -0.00427 C92 1 -0.042600 0.869828 0.916151 11.00000 0.02971 0.02533 = 0.03409 0.00297 0.01133 -0.00515 C93 1 -0.322188 0.633868 0.631611 11.00000 0.05077 0.02946 = 0.02802 -0.00631 0.02147 -0.01503 AFIX 43 H9 2 -0.322779 0.598525 0.585810 11.00000 -1.20000 AFIX 0 C94 1 1.043520 0.085293 0.781775 11.00000 0.03476 0.01737 = 0.05076 0.01258 0.02726 0.00875 C95 1 0.128689 0.822197 0.609619 11.00000 0.03449 0.03503 = 0.03299 0.01345 0.01193 -0.00292 AFIX 43 H10 2 0.078949 0.827657 0.558203 11.00000 -1.20000 AFIX 0 C96 1 -0.175656 0.681237 0.856070 11.00000 0.03275 0.01650 = 0.02650 -0.00154 0.01496 -0.00234 AFIX 43 H11 2 -0.174435 0.713952 0.903569 11.00000 -1.20000 AFIX 0 C97 1 0.123233 0.608104 0.741698 11.00000 0.03204 0.02510 = 0.03672 0.00836 0.01270 -0.00034 AFIX 43 H12 2 0.084659 0.590393 0.686357 11.00000 -1.20000 AFIX 0 C98 1 1.007684 0.100947 0.611886 11.00000 0.02892 0.02099 = 0.04032 0.00208 0.00937 0.00089 C99 1 0.639920 0.341375 0.867741 11.00000 0.05276 0.02666 = 0.03877 0.00775 0.03468 0.00962 AFIX 43 H13 2 0.604703 0.320859 0.894080 11.00000 -1.20000 AFIX 0 C100 1 -0.304112 0.909589 0.940263 11.00000 0.04624 0.01504 = 0.04273 0.00253 0.03138 0.00184 C101 1 -0.248901 0.895133 0.626113 11.00000 0.03995 0.02570 = 0.03052 0.00146 0.01468 -0.00649 AFIX 43 H14 2 -0.303157 0.914062 0.585849 11.00000 -1.20000 AFIX 0 C102 1 -0.447808 0.894693 0.832388 11.00000 0.03376 0.02202 = 0.05488 0.01349 0.03126 0.00567 AFIX 43 H15 2 -0.506419 0.910132 0.809475 11.00000 -1.20000 AFIX 0 C103 1 1.292270 0.098130 0.742201 11.00000 0.03730 0.02315 = 0.03871 -0.00508 0.02337 0.00090 AFIX 43 H16 2 1.267775 0.075678 0.778315 11.00000 -1.20000 AFIX 0 C104 1 -0.414582 0.841310 0.785845 11.00000 0.02480 0.02620 = 0.03438 0.01075 0.01746 0.00198 C105 1 0.712413 0.448373 0.462015 11.00000 0.05941 0.01903 = 0.02759 0.00034 0.02552 -0.00189 AFIX 43 H17 2 0.728787 0.474553 0.421073 11.00000 -1.20000 AFIX 0 C106 1 0.359057 0.814645 0.830998 11.00000 0.02695 0.02186 = 0.02610 -0.00217 0.01502 -0.00294 AFIX 43 H18 2 0.406072 0.779570 0.834088 11.00000 -1.20000 AFIX 0 C107 1 -0.130784 0.902931 0.994067 11.00000 0.03759 0.02334 = 0.02580 0.00018 0.00812 -0.00454 C108 1 0.817544 0.262312 0.726718 11.00000 0.03447 0.02442 = 0.02452 -0.00242 0.01801 0.00366 C109 1 0.409491 0.622169 0.959482 11.00000 0.03455 0.01761 = 0.03045 -0.00062 0.00713 -0.00342 C110 1 0.136412 0.868080 0.680651 11.00000 0.02959 0.02502 = 0.04215 0.01084 0.01707 -0.00023 AFIX 43 H19 2 0.090560 0.903917 0.679463 11.00000 -1.20000 AFIX 0 C111 1 0.446119 0.588010 0.703475 11.00000 0.03882 0.02140 = 0.05240 0.00521 0.03204 0.00123 C112 1 0.911174 0.197622 0.866317 11.00000 0.04876 0.03579 = 0.03203 0.00541 0.01452 0.02481 AFIX 43 H20 2 0.965289 0.195274 0.913090 11.00000 -1.20000 AFIX 0 C113 1 -0.174957 0.581806 0.720837 11.00000 0.04849 0.01993 = 0.05521 -0.00715 0.03914 -0.00638 AFIX 43 H21 2 -0.173699 0.548690 0.674575 11.00000 -1.20000 AFIX 0 C114 1 0.321322 0.679947 0.676331 11.00000 0.03283 0.02213 = 0.03255 -0.00181 0.01799 -0.00452 C115 1 0.390282 0.629358 0.736122 11.00000 0.03353 0.01927 = 0.03350 -0.00059 0.01896 -0.00294 C116 1 0.518849 0.332840 0.729730 11.00000 0.04339 0.01662 = 0.05517 0.00060 0.03238 0.00219 AFIX 43 H22 2 0.483848 0.311651 0.756053 11.00000 -1.20000 AFIX 0 C117 1 0.845440 0.150320 0.866647 11.00000 0.06097 0.03569 = 0.03810 0.01495 0.02756 0.02790 AFIX 43 H23 2 0.852395 0.117590 0.916098 11.00000 -1.20000 AFIX 0 C118 1 -0.164059 0.931704 1.051831 11.00000 0.05376 0.02597 = 0.02459 -0.00505 0.01683 -0.00903 AFIX 43 H24 2 -0.127806 0.945340 1.109135 11.00000 -1.20000 AFIX 0 C119 1 0.862466 0.433848 0.557050 11.00000 0.04551 0.02198 = 0.03632 -0.00429 0.02736 -0.00740 AFIX 43 H25 2 0.876298 0.462498 0.515458 11.00000 -1.20000 AFIX 0 C120 1 0.358454 0.625129 0.872965 11.00000 0.03559 0.01217 = 0.02827 0.00201 0.01713 0.00155 C121 1 0.377890 0.643380 1.020893 11.00000 0.05066 0.02688 = 0.02361 -0.00115 0.01223 -0.00125 AFIX 43 H26 2 0.415001 0.645555 1.079534 11.00000 -1.20000 AFIX 0 C122 1 1.375687 0.348938 0.851047 11.00000 0.03310 0.03485 = 0.07116 -0.03001 0.03241 -0.01423 AFIX 43 H27 2 1.425969 0.380559 0.858490 11.00000 -1.20000 AFIX 0 C123 1 -0.109740 0.624074 0.866217 11.00000 0.03603 0.02003 = 0.04520 0.00535 0.02120 0.00013 AFIX 43 H28 2 -0.064158 0.617368 0.920660 11.00000 -1.20000 AFIX 0 C124 1 0.627078 0.439102 0.443210 11.00000 0.04949 0.02264 = 0.01859 0.00041 0.00565 -0.00133 AFIX 43 H29 2 0.584572 0.452299 0.388305 11.00000 -1.20000 AFIX 0 C125 1 0.925516 0.407645 0.629949 11.00000 0.04202 0.02665 = 0.05255 -0.00766 0.03445 -0.00179 AFIX 43 H30 2 0.982863 0.424138 0.643814 11.00000 -1.20000 AFIX 0 C126 1 0.627530 0.078582 0.719695 11.00000 0.06113 0.01757 = 0.07842 0.00733 0.05553 0.00410 AFIX 43 H31 2 0.584532 0.038902 0.719448 11.00000 -1.20000 AFIX 0 C127 1 0.298700 0.921936 0.893957 11.00000 0.04236 0.02362 = 0.03142 -0.00627 0.02282 -0.00493 AFIX 43 H32 2 0.304851 0.959242 0.940521 11.00000 -1.20000 AFIX 0 C128 1 1.138543 0.092082 0.930446 11.00000 0.05678 0.02458 = 0.03467 0.00570 0.03064 0.01253 AFIX 43 H33 2 1.154345 0.073767 0.987529 11.00000 -1.20000 AFIX 0 C129 1 0.722424 0.365038 0.917476 11.00000 0.04969 0.03181 = 0.02879 0.00900 0.02133 0.01752 AFIX 43 H34 2 0.744753 0.359188 0.977464 11.00000 -1.20000 AFIX 0 C130 1 1.303303 0.353405 0.770783 11.00000 0.03884 0.02481 = 0.05894 -0.01825 0.03620 -0.01085 C131 1 -0.187230 0.866402 0.598445 11.00000 0.05424 0.03119 = 0.02361 -0.00720 0.02401 -0.01606 AFIX 43 H35 2 -0.200429 0.863520 0.539485 11.00000 -1.20000 AFIX 0 C132 1 0.222664 0.917375 0.826303 11.00000 0.03901 0.02229 = 0.04670 0.00544 0.03071 0.00493 AFIX 43 H36 2 0.175827 0.951084 0.825684 11.00000 -1.20000 AFIX 0 C133 1 1.174964 0.172517 0.825354 11.00000 0.03148 0.02080 = 0.03017 0.00047 0.02035 0.00807 C134 1 -0.000505 0.834518 0.803826 11.00000 0.03369 0.01943 = 0.05139 -0.00071 0.02747 -0.00071 AFIX 43 H37 2 0.041054 0.815898 0.784581 11.00000 -1.20000 AFIX 0 C135 1 0.765640 0.147779 0.795071 11.00000 0.05642 0.02693 = 0.04183 0.00446 0.03859 0.01251 C136 1 0.903852 0.354574 0.685620 11.00000 0.03688 0.03003 = 0.03046 -0.01004 0.01944 -0.00267 C137 1 0.293708 0.660487 0.994282 11.00000 0.05711 0.02006 = 0.03116 0.00050 0.02494 -0.00034 AFIX 43 H38 2 0.272591 0.678658 1.034498 11.00000 -1.20000 AFIX 0 C138 1 1.374021 0.301204 0.915754 11.00000 0.03062 0.04549 = 0.05256 -0.02521 0.01918 -0.00557 AFIX 43 H39 2 1.420399 0.303430 0.970097 11.00000 -1.20000 AFIX 0 C139 1 0.342188 0.609086 0.557761 11.00000 0.06804 0.02530 = 0.03811 -0.00505 0.03855 -0.01400 AFIX 43 H40 2 0.321524 0.595638 0.498966 11.00000 -1.20000 AFIX 0 C140 1 1.224931 0.175300 0.519039 11.00000 0.07224 0.02444 = 0.04973 -0.00427 0.04928 -0.00351 AFIX 43 H41 2 1.250297 0.198517 0.483960 11.00000 -1.20000 AFIX 0 C141 1 0.294581 0.661446 0.589628 11.00000 0.05525 0.01765 = 0.03140 -0.00164 0.02758 -0.01222 C142 1 0.091940 0.638028 0.800385 11.00000 0.02808 0.02955 = 0.06846 0.01055 0.02808 0.00847 AFIX 43 H42 2 0.032426 0.644392 0.783635 11.00000 -1.20000 AFIX 0 C143 1 -0.109012 0.575946 0.797698 11.00000 0.03290 0.02617 = 0.05690 0.00092 0.02718 -0.00206 AFIX 43 H43 2 -0.061848 0.538826 0.805147 11.00000 -1.20000 AFIX 0 C144 1 1.192795 0.144927 0.907978 11.00000 0.03730 0.02718 = 0.02929 -0.00094 0.01772 0.01002 C145 1 0.483585 0.349206 0.644900 11.00000 0.02830 0.02826 = 0.04291 -0.00638 0.01848 -0.00554 AFIX 43 H44 2 0.423749 0.345333 0.613091 11.00000 -1.20000 AFIX 0 C146 1 0.147220 0.657740 0.881017 11.00000 0.04050 0.02567 = 0.04813 -0.00099 0.02988 -0.00249 AFIX 43 H45 2 0.125508 0.675996 0.920747 11.00000 -1.20000 AFIX 0 C147 1 1.061578 0.067500 0.867209 11.00000 0.05123 0.02396 = 0.05092 0.00780 0.03932 0.00990 AFIX 43 H46 2 1.020411 0.038320 0.881423 11.00000 -1.20000 AFIX 0 C148 1 1.102310 0.138566 0.540572 11.00000 0.05294 0.01603 = 0.03274 0.00037 0.02255 -0.00140 C149 1 0.962601 0.059755 0.717667 11.00000 0.03045 0.01674 = 0.06229 0.00873 0.02336 0.00370 AFIX 43 H47 2 0.921659 0.033451 0.734062 11.00000 -1.20000 AFIX 0 C150 1 1.140669 0.161107 0.485429 11.00000 0.08125 0.02813 = 0.03358 0.00307 0.03261 0.01234 AFIX 43 H48 2 1.107670 0.166113 0.425994 11.00000 -1.20000 AFIX 0 C151 1 1.154997 0.377108 0.623316 11.00000 0.06706 0.02074 = 0.04243 -0.00011 0.03683 -0.00123 AFIX 43 H49 2 1.104294 0.387466 0.573824 11.00000 -1.20000 AFIX 0 C152 1 0.677326 0.186590 0.648670 11.00000 0.04243 0.01748 = 0.04274 0.00095 0.02834 0.00250 AFIX 43 H50 2 0.668830 0.219210 0.598733 11.00000 -1.20000 AFIX 0 C153 1 1.155137 0.318360 0.684883 11.00000 0.04241 0.01698 = 0.04190 -0.00706 0.02880 -0.00562 AFIX 43 H51 2 1.103813 0.289030 0.677643 11.00000 -1.20000 AFIX 0 C154 1 0.022151 0.849640 0.887636 11.00000 0.02176 0.02732 = 0.04548 -0.00101 0.00868 -0.00249 AFIX 43 H52 2 0.080185 0.846862 0.926828 11.00000 -1.20000 AFIX 0 C155 1 0.493398 0.589933 0.877079 11.00000 0.02934 0.02261 = 0.05173 0.00372 0.01541 0.00073 C156 1 -0.394283 0.922914 0.909761 11.00000 0.05085 0.02168 = 0.05170 0.00643 0.03913 0.00396 AFIX 43 H53 2 -0.416403 0.952192 0.944946 11.00000 -1.20000 AFIX 0 C157 1 -0.249832 0.939114 1.022292 11.00000 0.06922 0.02097 = 0.03972 -0.00184 0.04129 -0.00129 AFIX 43 H54 2 -0.273802 0.964724 1.057609 11.00000 -1.20000 AFIX 0 C158 1 0.552238 0.560721 0.844868 11.00000 0.02488 0.02441 = 0.07333 0.00411 0.02010 0.00452 AFIX 43 H55 2 0.608705 0.544889 0.882241 11.00000 -1.20000 AFIX 0 C159 1 1.378693 0.097889 0.769157 11.00000 0.03752 0.03075 = 0.05741 -0.01393 0.02521 -0.00100 AFIX 43 H56 2 1.413778 0.075506 0.823951 11.00000 -1.20000 AFIX 0 C160 1 0.943154 0.072056 0.634991 11.00000 0.02795 0.02179 = 0.05405 0.00830 0.01125 0.00111 AFIX 43 H57 2 0.887169 0.061469 0.593256 11.00000 -1.20000 AFIX 0 C161 1 1.367160 0.157800 0.637558 11.00000 0.06698 0.03177 = 0.07844 -0.01816 0.06299 -0.01771 AFIX 43 H58 2 1.393204 0.178423 0.602144 11.00000 -1.20000 AFIX 0 C162 1 0.526375 0.555857 0.759958 11.00000 0.04261 0.02053 = 0.07274 -0.00409 0.04055 0.00086 AFIX 43 H59 2 0.563147 0.530148 0.737737 11.00000 -1.20000 AFIX 0 C163 1 0.615851 0.126393 0.646123 11.00000 0.04040 0.02599 = 0.05513 -0.00071 0.03021 -0.00056 AFIX 43 H60 2 0.566273 0.117490 0.595163 11.00000 -1.20000 AFIX 0 C164 1 0.700757 0.088882 0.791974 11.00000 0.06529 0.02557 = 0.05189 0.00988 0.04620 0.00953 AFIX 43 H61 2 0.708001 0.055550 0.841187 11.00000 -1.20000 AFIX 0 C165 1 1.301484 0.410393 0.705877 11.00000 0.06007 0.02651 = 0.07365 -0.02570 0.05162 -0.02290 AFIX 43 H62 2 1.351588 0.441911 0.712538 11.00000 -1.20000 AFIX 0 C166 1 1.230700 0.421354 0.634742 11.00000 0.09529 0.02171 = 0.07012 -0.00853 0.06906 -0.01803 AFIX 43 H63 2 1.231626 0.459578 0.591352 11.00000 -1.20000 AFIX 0 C167 1 1.416037 0.130414 0.716600 11.00000 0.04367 0.04045 = 0.06815 -0.01780 0.03854 -0.00604 AFIX 43 H64 2 1.476243 0.133029 0.737149 11.00000 -1.20000 AFIX 0 HKLF 4 1 0 0 -1 0 -1 0 -1 0 0 REM 91119yuk_a.res in P2(1) REM R1 = 0.0505 for 13987 Fo > 4sig(Fo) and 0.0527 for all 14733 data REM 1153 parameters refined using 1 restraints END WGHT 0.0275 6.3906 REM Instructions for potential hydrogen bonds HTAB C124 S1_$1 HTAB C160 S3_$2 REM Highest difference peak 0.365, deepest hole -0.362, 1-sigma level 0.066 Q1 1 0.9773 0.1031 0.5474 11.00000 0.05 0.37 Q2 1 1.3286 0.2194 0.9671 11.00000 0.05 0.32 Q3 1 0.9462 0.2833 0.8040 11.00000 0.05 0.27 Q4 1 1.4685 0.2481 1.0173 11.00000 0.05 0.26 Q5 1 0.2121 0.4943 0.7893 11.00000 0.05 0.25 Q6 1 -0.4577 0.9958 0.9458 11.00000 0.05 0.25 Q7 1 0.7136 0.5184 0.8091 11.00000 0.05 0.25 Q8 1 0.0124 0.6193 0.7104 11.00000 0.05 0.24 Q9 1 0.2775 0.7240 0.8584 11.00000 0.05 0.24 Q10 1 0.0891 0.5830 0.6504 11.00000 0.05 0.24 Q11 1 0.9858 0.2341 1.0024 11.00000 0.05 0.24 Q12 1 0.2484 0.6835 0.5362 11.00000 0.05 0.23 Q13 1 0.1061 0.4732 0.4754 11.00000 0.05 0.23 Q14 1 0.7652 0.0216 0.9123 11.00000 0.05 0.23 Q15 1 1.2684 0.2436 0.4519 11.00000 0.05 0.23 Q16 1 0.7868 0.2741 1.0008 11.00000 0.05 0.23 Q17 1 0.2265 0.7277 0.6679 11.00000 0.05 0.23 Q18 1 -0.0100 0.8720 0.9757 11.00000 0.05 0.22 Q19 1 1.4739 0.1757 0.8189 11.00000 0.05 0.22 Q20 1 0.3318 0.7583 0.5784 11.00000 0.05 0.22 ; _shelx_res_checksum 79841