# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2017 ####################################################################### # # 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_murayama20170223 _audit_block_doi 10.5517/ccdc.csd.cc1p8rj7 _database_code_depnum_ccdc_archive 'CCDC 1557549' _audit_update_record ; 2017-06-21 deposited with the CCDC. 2017-11-30 downloaded from the CCDC. ; _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H38 N2 O3 S' _chemical_formula_iupac ? _chemical_formula_weight 614.77 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' 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 16.5942(7) _cell_length_b 8.7199(4) _cell_length_c 21.4742(10) _cell_angle_alpha 90 _cell_angle_beta 93.5160(10) _cell_angle_gamma 90 _cell_volume 3101.5(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9913 _cell_measurement_theta_min 2.3260 _cell_measurement_theta_max 24.9935 _cell_measurement_temperature 123.0(2) _exptl_crystal_description ? _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; ; _diffrn_ambient_temperature 123.0(2) _diffrn_source 'sealed tube' _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_reflns_number 20548 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_unetI/netI 0.0240 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _refine_special_details ; ; _reflns_number_total 5453 _reflns_number_gt 4679 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_gt 0.0940 _refine_ls_wR_factor_ref 0.0992 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_number_reflns 5453 _refine_ls_number_parameters 410 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+2.1814P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.400 _refine_diff_density_min -0.756 _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_extinction_coef 0.0058(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v3.0.29' _computing_cell_refinement 'SAINT V8.32B (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'XSHELL V6.3.1 (Bruke AXS)' _computing_publication_material 'Generate Report (Bruker AXS)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.60561(10) 0.42658(19) 0.30165(8) 0.0191(4) Uani d . . . 1 . . C C2 0.67844(10) 0.41205(18) 0.34428(8) 0.0175(4) Uani d . . . 1 . . C C3 0.67557(10) 0.46057(18) 0.40451(8) 0.0170(3) Uani d . . . 1 . . C C4 0.61268(10) 0.56535(18) 0.42146(8) 0.0182(4) Uani d . . . 1 . . C C5 0.61468(10) 0.64268(19) 0.47913(8) 0.0215(4) Uani d . . . 1 . . H H5 0.6549 0.6164 0.5107 0.026 Uiso calc U . R 1 . . C C6 0.55970(11) 0.7552(2) 0.49074(9) 0.0245(4) Uani d . . . 1 . . H H6 0.5624 0.8067 0.5298 0.029 Uiso calc U . R 1 . . C C7 0.49987(10) 0.7935(2) 0.44485(9) 0.0243(4) Uani d . . . 1 . . H H7 0.463 0.8738 0.4523 0.029 Uiso calc U . R 1 . . C C8 0.49360(10) 0.7161(2) 0.38887(8) 0.0226(4) Uani d . . . 1 . . H H8 0.4516 0.7408 0.3585 0.027 Uiso calc U . R 1 . . C C9 0.54951(10) 0.60069(19) 0.37690(8) 0.0188(4) Uani d . . . 1 . . C C10 0.73396(10) 0.40018(18) 0.45500(7) 0.0168(3) Uani d . . . 1 . . H H10 0.758 0.4864 0.4806 0.02 Uiso calc U . R 1 . . C C11 0.68519(10) 0.2907(2) 0.49636(8) 0.0215(4) Uani d . . . 1 . . H H11 0.631 0.3307 0.5064 0.026 Uiso calc U . R 1 . . C C12 0.73942(11) 0.2414(2) 0.55368(8) 0.0259(4) Uani d . . . 1 . . H H12A 0.7071 0.1947 0.586 0.031 Uiso calc U . R 1 . . H H12B 0.7699 0.3297 0.572 0.031 Uiso calc U . R 1 . . C C13 0.79705(11) 0.1217(2) 0.52647(8) 0.0249(4) Uani d . . . 1 . . H H13A 0.8543 0.1494 0.5361 0.03 Uiso calc U . R 1 . . H H13B 0.7871 0.0177 0.5428 0.03 Uiso calc U . R 1 . . C C14 0.77474(10) 0.13134(19) 0.45582(8) 0.0212(4) Uani d . . . 1 . . H H14 0.7941 0.0429 0.4311 0.025 Uiso calc U . R 1 . . C C15 0.80181(10) 0.29237(18) 0.43263(8) 0.0171(3) Uani d . . . 1 . . H H15 0.8534 0.3201 0.4564 0.02 Uiso calc U . R 1 . . C C16 0.68236(10) 0.1455(2) 0.45604(9) 0.0233(4) Uani d . . . 1 . . H H16A 0.6563 0.1625 0.4139 0.028 Uiso calc U . R 1 . . H H16B 0.6571 0.0575 0.4765 0.028 Uiso calc U . R 1 . . C C17 0.81662(10) 0.29694(18) 0.36345(8) 0.0170(3) Uani d . . . 1 . . C C18 0.89235(10) 0.25551(19) 0.34003(8) 0.0194(4) Uani d . . . 1 . . C C19 0.89808(11) 0.2521(2) 0.27544(8) 0.0248(4) Uani d . . . 1 . . H H19 0.9472 0.2193 0.2592 0.03 Uiso calc U . R 1 . . C C20 0.83478(11) 0.2948(2) 0.23436(8) 0.0268(4) Uani d . . . 1 . . H H20 0.8406 0.2903 0.1907 0.032 Uiso calc U . R 1 . . C C21 0.76363(11) 0.3435(2) 0.25674(8) 0.0232(4) Uani d . . . 1 . . H H21 0.7211 0.3778 0.2285 0.028 Uiso calc U . R 1 . . C C22 0.75292(10) 0.34312(18) 0.32115(8) 0.0182(4) Uani d . . . 1 . . C C23 0.46658(10) 0.5161(2) 0.28277(8) 0.0215(4) Uani d . . . 1 . . H H23A 0.4759 0.4755 0.2408 0.026 Uiso calc U . R 1 A 1 H H23B 0.4456 0.6219 0.2778 0.026 Uiso calc U . R 1 A 1 C C24 0.40439(10) 0.4181(2) 0.31232(8) 0.0205(4) Uani d . . . 1 B 1 C C25 0.32925(10) 0.4777(2) 0.32450(9) 0.0272(4) Uani d . . . 1 B 1 H H25 0.3183 0.5832 0.317 0.033 Uiso calc U . R 1 B 1 C C26 0.27020(11) 0.3849(3) 0.34747(9) 0.0342(5) Uani d . . . 1 B 1 H H26 0.219 0.4269 0.3555 0.041 Uiso calc U . R 1 B 1 C C27 0.28560(12) 0.2314(3) 0.35872(9) 0.0348(5) Uani d . . . 1 B 1 H H27 0.245 0.1676 0.3744 0.042 Uiso calc U . R 1 B 1 C C28 0.36025(12) 0.1706(2) 0.34710(9) 0.0309(4) Uani d . . . 1 B 1 H H28 0.3709 0.065 0.3548 0.037 Uiso calc U . R 1 B 1 C C29 0.41941(11) 0.2632(2) 0.32432(8) 0.0248(4) Uani d . . . 1 B 1 H H29 0.4707 0.2209 0.3168 0.03 Uiso calc U . R 1 B 1 C C30 0.97058(10) 0.2185(2) 0.38100(8) 0.0213(4) Uani d . . . 1 . . C C31 0.96133(11) 0.0843(2) 0.42596(9) 0.0259(4) Uani d . . . 1 . . H H31A 1.0141 0.0588 0.4463 0.039 Uiso calc U . R 1 . . H H31B 0.9399 -0.0049 0.4027 0.039 Uiso calc U . R 1 . . H H31C 0.9241 0.1133 0.4577 0.039 Uiso calc U . R 1 . . C C32 1.04215(11) 0.1742(2) 0.34224(9) 0.0275(4) Uani d . . . 1 . . H H32A 1.0524 0.2568 0.3129 0.041 Uiso calc U . R 1 . . H H32B 1.0292 0.0796 0.3191 0.041 Uiso calc U . R 1 . . H H32C 1.0903 0.1578 0.3702 0.041 Uiso calc U . R 1 . . C C33 0.92537(10) 0.62201(19) 0.38066(8) 0.0197(4) Uani d . . . 1 C 1 C C34 0.90018(11) 0.6492(2) 0.31887(8) 0.0257(4) Uani d . . . 1 C 1 H H34 0.932 0.6151 0.2863 0.031 Uiso calc U . R 1 C 1 C C35 0.82845(12) 0.7263(2) 0.30496(8) 0.0280(4) Uani d . . . 1 C 1 H H35 0.8117 0.7459 0.2626 0.034 Uiso calc U . R 1 C 1 C C36 0.78042(11) 0.77567(19) 0.35209(8) 0.0226(4) Uani d . . . 1 C 1 C C37 0.80668(10) 0.74595(19) 0.41383(8) 0.0205(4) Uani d . . . 1 C 1 H H37 0.7745 0.7785 0.4465 0.025 Uiso calc U . R 1 C 1 C C38 0.87869(10) 0.66998(19) 0.42861(8) 0.0198(4) Uani d . . . 1 C 1 H H38 0.8959 0.651 0.4709 0.024 Uiso calc U . R 1 C 1 C C39 0.70216(11) 0.8581(2) 0.33615(9) 0.0292(4) Uani d . . . 1 C 1 H H39A 0.6716 0.867 0.3736 0.044 Uiso calc U . R 1 C 1 H H39B 0.6704 0.8002 0.3042 0.044 Uiso calc U . R 1 C 1 H H39C 0.7135 0.9607 0.3203 0.044 Uiso calc U . R 1 C 1 N N1 0.54421(8) 0.51934(16) 0.32071(6) 0.0188(3) Uani d . . . 1 . . N N2 0.99758(8) 0.35136(16) 0.42145(6) 0.0198(3) Uani d . . . 1 . . H H2A 1.0433 0.3193 0.4432 0.024 Uiso calc U . R 1 . . H H2B 0.9595 0.3617 0.4499 0.024 Uiso calc U . R 1 . . O O1 0.59543(7) 0.35374(14) 0.25233(6) 0.0241(3) Uani d . . . 1 . . O O2 1.05464(7) 0.59733(15) 0.45288(6) 0.0251(3) Uani d . . . 1 . . O O3 1.05945(7) 0.51613(15) 0.34274(6) 0.0269(3) Uani d . . . 1 . . S S1 1.01664(2) 0.52350(5) 0.39844(2) 0.02028(13) Uani d . . . 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0184(9) 0.0171(8) 0.0215(9) -0.0027(7) 0.0001(7) 0.0003(7) C2 0.0165(8) 0.0149(8) 0.0211(9) -0.0023(6) 0.0005(7) -0.0002(7) C3 0.0143(8) 0.0148(8) 0.0221(9) -0.0045(6) 0.0020(7) 0.0004(7) C4 0.0162(8) 0.0165(8) 0.0221(9) -0.0020(7) 0.0024(7) 0.0004(7) C5 0.0212(9) 0.0228(9) 0.0206(9) -0.0010(7) 0.0014(7) -0.0017(7) C6 0.0245(9) 0.0243(9) 0.0250(9) -0.0011(7) 0.0045(7) -0.0051(7) C7 0.0202(9) 0.0210(9) 0.0324(10) 0.0021(7) 0.0064(8) -0.0021(8) C8 0.0162(8) 0.0225(9) 0.0291(10) 0.0003(7) 0.0007(7) 0.0012(7) C9 0.0171(8) 0.0180(8) 0.0216(9) -0.0031(7) 0.0023(7) 0.0000(7) C10 0.0164(8) 0.0164(8) 0.0179(8) -0.0014(7) 0.0023(7) -0.0012(6) C11 0.0194(9) 0.0214(9) 0.0243(9) -0.0001(7) 0.0071(7) 0.0033(7) C12 0.0290(10) 0.0277(10) 0.0217(9) 0.0015(8) 0.0065(8) 0.0053(8) C13 0.0272(10) 0.0219(9) 0.0260(10) 0.0016(8) 0.0051(8) 0.0076(7) C14 0.0225(9) 0.0168(8) 0.0247(9) -0.0008(7) 0.0038(7) 0.0006(7) C15 0.0151(8) 0.0177(8) 0.0183(8) 0.0001(7) 0.0005(6) 0.0001(7) C16 0.0222(9) 0.0203(9) 0.0278(10) -0.0050(7) 0.0043(7) 0.0026(7) C17 0.0178(8) 0.0130(8) 0.0202(9) -0.0023(6) 0.0014(7) -0.0015(6) C18 0.0183(9) 0.0187(8) 0.0211(9) 0.0004(7) 0.0012(7) -0.0015(7) C19 0.0188(9) 0.0338(10) 0.0222(9) 0.0031(8) 0.0041(7) -0.0043(8) C20 0.0242(9) 0.0392(11) 0.0170(9) 0.0015(8) 0.0014(7) -0.0037(8) C21 0.0200(9) 0.0288(9) 0.0202(9) 0.0008(7) -0.0034(7) -0.0026(7) C22 0.0176(8) 0.0165(8) 0.0205(9) -0.0025(7) 0.0006(7) -0.0020(7) C23 0.0180(9) 0.0244(9) 0.0213(9) 0.0019(7) -0.0046(7) 0.0008(7) C24 0.0180(8) 0.0267(9) 0.0160(8) -0.0007(7) -0.0051(7) -0.0036(7) C25 0.0193(9) 0.0322(10) 0.0293(10) 0.0026(8) -0.0039(8) -0.0100(8) C26 0.0182(9) 0.0534(13) 0.0311(11) -0.0027(9) 0.0025(8) -0.0120(9) C27 0.0281(11) 0.0494(13) 0.0270(10) -0.0156(9) 0.0016(8) -0.0006(9) C28 0.0318(11) 0.0318(10) 0.0283(10) -0.0063(9) -0.0043(8) 0.0035(8) C29 0.0200(9) 0.0291(10) 0.0246(9) 0.0005(8) -0.0028(7) -0.0001(8) C30 0.0187(9) 0.0240(9) 0.0212(9) 0.0025(7) 0.0014(7) -0.0012(7) C31 0.0239(9) 0.0251(9) 0.0289(10) 0.0062(8) 0.0022(8) 0.0033(8) C32 0.0202(9) 0.0362(10) 0.0262(10) 0.0073(8) 0.0026(7) -0.0012(8) C33 0.0201(9) 0.0194(8) 0.0193(9) -0.0046(7) -0.0008(7) 0.0027(7) C34 0.0291(10) 0.0303(10) 0.0176(9) -0.0011(8) 0.0015(7) 0.0025(7) C35 0.0337(11) 0.0313(10) 0.0181(9) -0.0007(8) -0.0048(8) 0.0046(8) C36 0.0239(9) 0.0166(8) 0.0264(9) -0.0051(7) -0.0039(7) 0.0023(7) C37 0.0220(9) 0.0164(8) 0.0231(9) -0.0033(7) 0.0009(7) -0.0001(7) C38 0.0232(9) 0.0189(8) 0.0169(8) -0.0043(7) -0.0008(7) 0.0016(7) C39 0.0301(10) 0.0265(10) 0.0301(10) 0.0007(8) -0.0072(8) 0.0037(8) N1 0.0145(7) 0.0208(7) 0.0206(7) -0.0001(6) -0.0022(6) -0.0009(6) N2 0.0131(7) 0.0281(8) 0.0181(7) 0.0021(6) -0.0001(6) 0.0030(6) O1 0.0211(6) 0.0266(6) 0.0239(7) 0.0001(5) -0.0039(5) -0.0078(5) O2 0.0195(6) 0.0344(7) 0.0211(6) -0.0068(5) -0.0022(5) -0.0003(5) O3 0.0223(6) 0.0371(7) 0.0219(7) -0.0023(6) 0.0069(5) 0.0035(5) S1 0.0165(2) 0.0276(2) 0.0169(2) -0.00307(17) 0.00133(16) 0.00200(17) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 O1 . 1.238(2) ? C1 N1 . 1.382(2) ? C1 C2 . 1.476(2) ? C2 C3 . 1.364(2) ? C2 C22 . 1.487(2) ? C3 C4 . 1.450(2) ? C3 C10 . 1.504(2) ? C4 C5 . 1.409(2) ? C4 C9 . 1.409(2) ? C5 C6 . 1.373(2) ? C5 H5 . 0.95 ? C6 C7 . 1.396(3) ? C6 H6 . 0.95 ? C7 C8 . 1.377(3) ? C7 H7 . 0.95 ? C8 C9 . 1.403(2) ? C8 H8 . 0.95 ? C9 N1 . 1.398(2) ? C10 C11 . 1.563(2) ? C10 C15 . 1.565(2) ? C10 H10 . 1.0 ? C11 C16 . 1.533(2) ? C11 C12 . 1.541(3) ? C11 H11 . 1.0 ? C12 C13 . 1.553(2) ? C12 H12A . 0.99 ? C12 H12B . 0.99 ? C13 C14 . 1.542(2) ? C13 H13A . 0.99 ? C13 H13B . 0.99 ? C14 C16 . 1.538(2) ? C14 C15 . 1.565(2) ? C14 H14 . 1.0 ? C15 C17 . 1.521(2) ? C15 H15 . 1.0 ? C16 H16A . 0.99 ? C16 H16B . 0.99 ? C17 C22 . 1.410(2) ? C17 C18 . 1.428(2) ? C18 C19 . 1.396(2) ? C18 C30 . 1.557(2) ? C19 C20 . 1.381(3) ? C19 H19 . 0.95 ? C20 C21 . 1.369(2) ? C20 H20 . 0.95 ? C21 C22 . 1.405(2) ? C21 H21 . 0.95 ? C23 N1 . 1.482(2) ? C23 C24 . 1.509(2) ? C23 H23A . 0.99 ? C23 H23B . 0.99 ? C24 C25 . 1.390(2) ? C24 C29 . 1.394(3) ? C25 C26 . 1.385(3) ? C25 H25 . 0.95 ? C26 C27 . 1.382(3) ? C26 H26 . 0.95 ? C27 C28 . 1.384(3) ? C27 H27 . 0.95 ? C28 C29 . 1.384(3) ? C28 H28 . 0.95 ? C29 H29 . 0.95 ? C30 N2 . 1.500(2) ? C30 C31 . 1.531(2) ? C30 C32 . 1.541(2) ? C31 H31A . 0.98 ? C31 H31B . 0.98 ? C31 H31C . 0.98 ? C32 H32A . 0.98 ? C32 H32B . 0.98 ? C32 H32C . 0.98 ? C33 C34 . 1.387(2) ? C33 C38 . 1.390(2) ? C33 S1 . 1.7626(17) ? C34 C35 . 1.384(3) ? C34 H34 . 0.95 ? C35 C36 . 1.394(3) ? C35 H35 . 0.95 ? C36 C37 . 1.394(2) ? C36 C39 . 1.505(3) ? C37 C38 . 1.386(2) ? C37 H37 . 0.95 ? C38 H38 . 0.95 ? C39 H39A . 0.98 ? C39 H39B . 0.98 ? C39 H39C . 0.98 ? N2 S1 . 1.6175(14) ? N2 H2A . 0.91 ? N2 H2B . 0.91 ? O2 S1 . 1.4451(13) ? O3 S1 . 1.4296(12) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 C1 N1 . . 119.29(15) ? O1 C1 C2 . . 123.38(15) ? N1 C1 C2 . . 117.18(14) ? C3 C2 C1 . . 119.11(15) ? C3 C2 C22 . . 121.33(15) ? C1 C2 C22 . . 119.55(14) ? C2 C3 C4 . . 120.05(15) ? C2 C3 C10 . . 121.09(15) ? C4 C3 C10 . . 118.76(14) ? C5 C4 C9 . . 117.94(15) ? C5 C4 C3 . . 122.94(16) ? C9 C4 C3 . . 118.95(15) ? C6 C5 C4 . . 121.44(17) ? C6 C5 H5 . . 119.3 ? C4 C5 H5 . . 119.3 ? C5 C6 C7 . . 119.64(17) ? C5 C6 H6 . . 120.2 ? C7 C6 H6 . . 120.2 ? C8 C7 C6 . . 120.78(16) ? C8 C7 H7 . . 119.6 ? C6 C7 H7 . . 119.6 ? C7 C8 C9 . . 119.72(17) ? C7 C8 H8 . . 120.1 ? C9 C8 H8 . . 120.1 ? N1 C9 C8 . . 120.98(15) ? N1 C9 C4 . . 118.68(15) ? C8 C9 C4 . . 120.34(15) ? C3 C10 C11 . . 106.88(13) ? C3 C10 C15 . . 115.64(13) ? C11 C10 C15 . . 102.41(13) ? C3 C10 H10 . . 110.5 ? C11 C10 H10 . . 110.5 ? C15 C10 H10 . . 110.5 ? C16 C11 C12 . . 102.52(14) ? C16 C11 C10 . . 100.52(13) ? C12 C11 C10 . . 109.09(14) ? C16 C11 H11 . . 114.4 ? C12 C11 H11 . . 114.4 ? C10 C11 H11 . . 114.4 ? C11 C12 C13 . . 103.29(14) ? C11 C12 H12A . . 111.1 ? C13 C12 H12A . . 111.1 ? C11 C12 H12B . . 111.1 ? C13 C12 H12B . . 111.1 ? H12A C12 H12B . . 109.1 ? C14 C13 C12 . . 102.56(14) ? C14 C13 H13A . . 111.3 ? C12 C13 H13A . . 111.3 ? C14 C13 H13B . . 111.3 ? C12 C13 H13B . . 111.3 ? H13A C13 H13B . . 109.2 ? C16 C14 C13 . . 100.40(14) ? C16 C14 C15 . . 103.58(13) ? C13 C14 C15 . . 107.78(14) ? C16 C14 H14 . . 114.5 ? C13 C14 H14 . . 114.5 ? C15 C14 H14 . . 114.5 ? C17 C15 C14 . . 113.64(13) ? C17 C15 C10 . . 116.52(13) ? C14 C15 C10 . . 102.44(12) ? C17 C15 H15 . . 107.9 ? C14 C15 H15 . . 107.9 ? C10 C15 H15 . . 107.9 ? C11 C16 C14 . . 94.12(13) ? C11 C16 H16A . . 112.9 ? C14 C16 H16A . . 112.9 ? C11 C16 H16B . . 112.9 ? C14 C16 H16B . . 112.9 ? H16A C16 H16B . . 110.3 ? C22 C17 C18 . . 119.11(15) ? C22 C17 C15 . . 118.50(14) ? C18 C17 C15 . . 122.39(15) ? C19 C18 C17 . . 118.04(16) ? C19 C18 C30 . . 116.86(14) ? C17 C18 C30 . . 125.07(15) ? C20 C19 C18 . . 122.23(16) ? C20 C19 H19 . . 118.9 ? C18 C19 H19 . . 118.9 ? C21 C20 C19 . . 119.86(16) ? C21 C20 H20 . . 120.1 ? C19 C20 H20 . . 120.1 ? C20 C21 C22 . . 120.57(17) ? C20 C21 H21 . . 119.7 ? C22 C21 H21 . . 119.7 ? C21 C22 C17 . . 119.99(15) ? C21 C22 C2 . . 119.06(15) ? C17 C22 C2 . . 120.40(15) ? N1 C23 C24 . . 111.94(14) ? N1 C23 H23A . . 109.2 ? C24 C23 H23A . . 109.2 ? N1 C23 H23B . . 109.2 ? C24 C23 H23B . . 109.2 ? H23A C23 H23B . . 107.9 ? C25 C24 C29 . . 118.65(17) ? C25 C24 C23 . . 120.77(16) ? C29 C24 C23 . . 120.46(15) ? C26 C25 C24 . . 120.74(18) ? C26 C25 H25 . . 119.6 ? C24 C25 H25 . . 119.6 ? C27 C26 C25 . . 120.07(18) ? C27 C26 H26 . . 120.0 ? C25 C26 H26 . . 120.0 ? C26 C27 C28 . . 119.85(18) ? C26 C27 H27 . . 120.1 ? C28 C27 H27 . . 120.1 ? C29 C28 C27 . . 120.16(19) ? C29 C28 H28 . . 119.9 ? C27 C28 H28 . . 119.9 ? C28 C29 C24 . . 120.53(17) ? C28 C29 H29 . . 119.7 ? C24 C29 H29 . . 119.7 ? N2 C30 C31 . . 105.24(14) ? N2 C30 C32 . . 107.11(14) ? C31 C30 C32 . . 105.02(14) ? N2 C30 C18 . . 112.12(13) ? C31 C30 C18 . . 113.72(14) ? C32 C30 C18 . . 112.98(14) ? C30 C31 H31A . . 109.5 ? C30 C31 H31B . . 109.5 ? H31A C31 H31B . . 109.5 ? C30 C31 H31C . . 109.5 ? H31A C31 H31C . . 109.5 ? H31B C31 H31C . . 109.5 ? C30 C32 H32A . . 109.5 ? C30 C32 H32B . . 109.5 ? H32A C32 H32B . . 109.5 ? C30 C32 H32C . . 109.5 ? H32A C32 H32C . . 109.5 ? H32B C32 H32C . . 109.5 ? C34 C33 C38 . . 120.55(16) ? C34 C33 S1 . . 119.68(13) ? C38 C33 S1 . . 119.77(13) ? C35 C34 C33 . . 119.63(17) ? C35 C34 H34 . . 120.2 ? C33 C34 H34 . . 120.2 ? C34 C35 C36 . . 121.05(17) ? C34 C35 H35 . . 119.5 ? C36 C35 H35 . . 119.5 ? C35 C36 C37 . . 118.27(16) ? C35 C36 C39 . . 120.40(16) ? C37 C36 C39 . . 121.33(16) ? C38 C37 C36 . . 121.43(16) ? C38 C37 H37 . . 119.3 ? C36 C37 H37 . . 119.3 ? C37 C38 C33 . . 119.06(16) ? C37 C38 H38 . . 120.5 ? C33 C38 H38 . . 120.5 ? C36 C39 H39A . . 109.5 ? C36 C39 H39B . . 109.5 ? H39A C39 H39B . . 109.5 ? C36 C39 H39C . . 109.5 ? H39A C39 H39C . . 109.5 ? H39B C39 H39C . . 109.5 ? C1 N1 C9 . . 122.96(14) ? C1 N1 C23 . . 117.24(14) ? C9 N1 C23 . . 119.41(13) ? C30 N2 S1 . . 126.64(11) ? C30 N2 H2A . . 105.7 ? S1 N2 H2A . . 105.7 ? C30 N2 H2B . . 105.7 ? S1 N2 H2B . . 105.7 ? H2A N2 H2B . . 106.1 ? O3 S1 O2 . . 118.84(7) ? O3 S1 N2 . . 109.30(8) ? O2 S1 N2 . . 104.48(7) ? O3 S1 C33 . . 107.77(8) ? O2 S1 C33 . . 106.54(8) ? N2 S1 C33 . . 109.69(8) ? _shelx_res_file ; murayama20170223_0m_a.res created by SHELXL-2014/7 TITL murayama20170223_0m_a.res in P2(1)/c CELL 0.71073 16.5942 8.7199 21.4742 90.000 93.516 90.000 ZERR 4.000 0.0007 0.0004 0.0010 0.000 0.001 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O S UNIT 156 152 8 12 4 REM Old TITL murayama20170223_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.115, Rweak 0.002, Alpha 0.019, Orientation as input REM Formula found by SHELXT: C39 N2 O3 S L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.05 0.20 0.25 TEMP -150.000 WGHT 0.045400 2.181400 EXTI 0.005768 FVAR 0.48809 C1 1 0.605610 0.426579 0.301648 11.00000 0.01843 0.01713 = 0.02152 0.00034 0.00010 -0.00271 C2 1 0.678441 0.412053 0.344278 11.00000 0.01648 0.01492 = 0.02114 -0.00018 0.00047 -0.00233 C3 1 0.675570 0.460566 0.404507 11.00000 0.01430 0.01485 = 0.02209 0.00042 0.00199 -0.00447 C4 1 0.612681 0.565349 0.421460 11.00000 0.01619 0.01646 = 0.02209 0.00038 0.00245 -0.00196 C5 1 0.614679 0.642682 0.479134 11.00000 0.02117 0.02284 = 0.02063 -0.00169 0.00141 -0.00104 AFIX 43 H5 2 0.654949 0.616405 0.510682 11.00000 -1.20000 AFIX 0 C6 1 0.559705 0.755180 0.490742 11.00000 0.02447 0.02435 = 0.02502 -0.00511 0.00447 -0.00111 AFIX 43 H6 2 0.562367 0.806691 0.529796 11.00000 -1.20000 AFIX 0 C7 1 0.499874 0.793469 0.444850 11.00000 0.02022 0.02097 = 0.03242 -0.00210 0.00642 0.00209 AFIX 43 H7 2 0.463047 0.873841 0.452333 11.00000 -1.20000 AFIX 0 C8 1 0.493603 0.716130 0.388866 11.00000 0.01621 0.02249 = 0.02908 0.00123 0.00067 0.00031 AFIX 43 H8 2 0.451603 0.740812 0.358463 11.00000 -1.20000 AFIX 0 C9 1 0.549511 0.600688 0.376904 11.00000 0.01708 0.01802 = 0.02157 0.00000 0.00235 -0.00306 C10 1 0.733959 0.400177 0.455004 11.00000 0.01638 0.01639 = 0.01792 -0.00119 0.00227 -0.00141 AFIX 13 H10 2 0.758001 0.486449 0.480586 11.00000 -1.20000 AFIX 0 C11 1 0.685190 0.290710 0.496363 11.00000 0.01943 0.02144 = 0.02426 0.00325 0.00708 -0.00007 AFIX 13 H11 2 0.631029 0.330712 0.506429 11.00000 -1.20000 AFIX 0 C12 1 0.739415 0.241370 0.553679 11.00000 0.02899 0.02766 = 0.02172 0.00526 0.00647 0.00147 AFIX 23 H12A 2 0.707118 0.194717 0.586001 11.00000 -1.20000 H12B 2 0.769944 0.329674 0.572014 11.00000 -1.20000 AFIX 0 C13 1 0.797050 0.121746 0.526473 11.00000 0.02724 0.02190 = 0.02597 0.00759 0.00508 0.00160 AFIX 23 H13A 2 0.854311 0.149445 0.536137 11.00000 -1.20000 H13B 2 0.787098 0.017698 0.542775 11.00000 -1.20000 AFIX 0 C14 1 0.774738 0.131341 0.455815 11.00000 0.02251 0.01681 = 0.02466 0.00062 0.00377 -0.00084 AFIX 13 H14 2 0.794051 0.042924 0.431087 11.00000 -1.20000 AFIX 0 C15 1 0.801809 0.292368 0.432634 11.00000 0.01512 0.01767 = 0.01830 0.00013 0.00045 0.00011 AFIX 13 H15 2 0.853444 0.320087 0.456430 11.00000 -1.20000 AFIX 0 C16 1 0.682355 0.145467 0.456036 11.00000 0.02221 0.02027 = 0.02778 0.00257 0.00428 -0.00496 AFIX 23 H16A 2 0.656270 0.162458 0.413898 11.00000 -1.20000 H16B 2 0.657052 0.057467 0.476460 11.00000 -1.20000 AFIX 0 C17 1 0.816621 0.296943 0.363452 11.00000 0.01782 0.01303 = 0.02020 -0.00151 0.00137 -0.00226 C18 1 0.892354 0.255508 0.340027 11.00000 0.01834 0.01873 = 0.02111 -0.00153 0.00123 0.00037 C19 1 0.898082 0.252073 0.275438 11.00000 0.01881 0.03376 = 0.02219 -0.00434 0.00406 0.00311 AFIX 43 H19 2 0.947199 0.219259 0.259209 11.00000 -1.20000 AFIX 0 C20 1 0.834775 0.294754 0.234356 11.00000 0.02417 0.03920 = 0.01698 -0.00370 0.00137 0.00153 AFIX 43 H20 2 0.840568 0.290321 0.190654 11.00000 -1.20000 AFIX 0 C21 1 0.763635 0.343477 0.256739 11.00000 0.01995 0.02876 = 0.02019 -0.00264 -0.00342 0.00076 AFIX 43 H21 2 0.721148 0.377825 0.228482 11.00000 -1.20000 AFIX 0 C22 1 0.752922 0.343117 0.321150 11.00000 0.01755 0.01651 = 0.02053 -0.00196 0.00062 -0.00251 C23 1 0.466581 0.516052 0.282775 11.00000 0.01796 0.02441 = 0.02128 0.00078 -0.00458 0.00190 AFIX 23 H23A 2 0.475868 0.475457 0.240761 11.00000 -1.20000 H23B 2 0.445643 0.621930 0.277762 11.00000 -1.20000 PART 1 AFIX 0 C24 1 0.404392 0.418055 0.312317 11.00000 0.01805 0.02671 = 0.01600 -0.00359 -0.00506 -0.00073 C25 1 0.329252 0.477662 0.324503 11.00000 0.01935 0.03223 = 0.02926 -0.01001 -0.00385 0.00257 AFIX 43 H25 2 0.318311 0.583210 0.316987 11.00000 -1.20000 AFIX 0 C26 1 0.270199 0.384904 0.347471 11.00000 0.01824 0.05335 = 0.03107 -0.01205 0.00246 -0.00273 AFIX 43 H26 2 0.219037 0.426884 0.355506 11.00000 -1.20000 AFIX 0 C27 1 0.285603 0.231359 0.358715 11.00000 0.02807 0.04944 = 0.02699 -0.00059 0.00162 -0.01561 AFIX 43 H27 2 0.245049 0.167648 0.374385 11.00000 -1.20000 AFIX 0 C28 1 0.360252 0.170572 0.347098 11.00000 0.03176 0.03181 = 0.02827 0.00349 -0.00430 -0.00634 AFIX 43 H28 2 0.370895 0.064987 0.354780 11.00000 -1.20000 AFIX 0 C29 1 0.419413 0.263197 0.324323 11.00000 0.02001 0.02910 = 0.02464 -0.00010 -0.00285 0.00050 AFIX 43 H29 2 0.470684 0.220946 0.316804 11.00000 -1.20000 PART 0 AFIX 0 C30 1 0.970583 0.218544 0.380996 11.00000 0.01868 0.02400 = 0.02123 -0.00116 0.00137 0.00250 C31 1 0.961327 0.084341 0.425959 11.00000 0.02388 0.02510 = 0.02889 0.00328 0.00224 0.00618 AFIX 137 H31A 2 1.014102 0.058801 0.446298 11.00000 -1.50000 H31B 2 0.939871 -0.004944 0.402709 11.00000 -1.50000 H31C 2 0.924083 0.113255 0.457654 11.00000 -1.50000 AFIX 0 C32 1 1.042153 0.174157 0.342241 11.00000 0.02016 0.03619 = 0.02622 -0.00121 0.00260 0.00735 AFIX 137 H32A 2 1.052433 0.256845 0.312855 11.00000 -1.50000 H32B 2 1.029203 0.079613 0.319065 11.00000 -1.50000 H32C 2 1.090345 0.157780 0.370154 11.00000 -1.50000 PART 1 AFIX 0 C33 1 0.925366 0.622010 0.380659 11.00000 0.02009 0.01938 = 0.01927 0.00266 -0.00081 -0.00463 C34 1 0.900183 0.649212 0.318867 11.00000 0.02913 0.03029 = 0.01762 0.00251 0.00146 -0.00105 AFIX 43 H34 2 0.932005 0.615102 0.286275 11.00000 -1.20000 AFIX 0 C35 1 0.828451 0.726310 0.304959 11.00000 0.03368 0.03128 = 0.01813 0.00460 -0.00483 -0.00066 AFIX 43 H35 2 0.811659 0.745921 0.262619 11.00000 -1.20000 AFIX 0 C36 1 0.780423 0.775673 0.352089 11.00000 0.02391 0.01665 = 0.02644 0.00225 -0.00388 -0.00506 C37 1 0.806681 0.745951 0.413829 11.00000 0.02200 0.01644 = 0.02306 -0.00008 0.00086 -0.00328 AFIX 43 H37 2 0.774519 0.778480 0.446470 11.00000 -1.20000 AFIX 0 C38 1 0.878687 0.669981 0.428614 11.00000 0.02322 0.01891 = 0.01694 0.00158 -0.00083 -0.00433 AFIX 43 H38 2 0.895907 0.650952 0.470915 11.00000 -1.20000 AFIX 0 C39 1 0.702162 0.858114 0.336150 11.00000 0.03006 0.02645 = 0.03012 0.00367 -0.00723 0.00070 AFIX 137 H39A 2 0.671641 0.867049 0.373631 11.00000 -1.50000 H39B 2 0.670363 0.800232 0.304169 11.00000 -1.50000 H39C 2 0.713531 0.960731 0.320275 11.00000 -1.50000 PART 0 AFIX 0 N1 3 0.544210 0.519337 0.320708 11.00000 0.01452 0.02082 = 0.02059 -0.00089 -0.00218 -0.00005 N2 3 0.997578 0.351362 0.421451 11.00000 0.01311 0.02806 = 0.01811 0.00304 -0.00005 0.00210 AFIX 23 H2A 2 1.043271 0.319269 0.443210 11.00000 -1.20000 H2B 2 0.959455 0.361712 0.449869 11.00000 -1.20000 AFIX 0 O1 4 0.595430 0.353736 0.252333 11.00000 0.02105 0.02658 = 0.02392 -0.00777 -0.00390 0.00012 O2 4 1.054637 0.597329 0.452881 11.00000 0.01947 0.03436 = 0.02110 -0.00034 -0.00220 -0.00679 O3 4 1.059450 0.516134 0.342740 11.00000 0.02235 0.03706 = 0.02189 0.00352 0.00690 -0.00234 S1 5 1.016639 0.523499 0.398440 11.00000 0.01645 0.02755 = 0.01688 0.00200 0.00133 -0.00307 HKLF 4 REM murayama20170223_0m_a.res in P2(1)/c REM R1 = 0.0371 for 4679 Fo > 4sig(Fo) and 0.0455 for all 5453 data REM 410 parameters refined using 0 restraints END WGHT 0.0458 2.1675 REM Highest difference peak 0.400, deepest hole -0.756, 1-sigma level 0.048 Q1 1 0.9887 0.3469 0.4660 11.00000 0.05 0.40 Q2 1 0.7141 0.3411 0.4774 11.00000 0.05 0.26 Q3 1 0.9637 0.5743 0.3893 11.00000 0.05 0.26 Q4 1 0.7900 0.2050 0.4427 11.00000 0.05 0.25 Q5 1 0.7971 0.7266 0.3301 11.00000 0.05 0.24 Q6 1 0.9027 0.6333 0.4001 11.00000 0.05 0.24 Q7 1 0.7667 0.3407 0.4383 11.00000 0.05 0.23 Q8 1 0.7325 0.1281 0.4513 11.00000 0.05 0.22 Q9 1 0.6384 0.4965 0.4180 11.00000 0.05 0.21 Q10 1 0.7104 0.3634 0.3338 11.00000 0.05 0.20 Q11 1 0.6877 0.4693 0.3684 11.00000 0.05 0.20 Q12 1 0.3750 0.4516 0.3301 11.00000 0.05 0.20 Q13 1 0.7999 0.7775 0.3789 11.00000 0.05 0.20 Q14 1 0.5145 0.7453 0.4756 11.00000 0.05 0.19 Q15 1 0.4858 0.7176 0.4277 11.00000 0.05 0.19 Q16 1 0.7854 0.1272 0.4851 11.00000 0.05 0.19 Q17 1 0.8534 0.7531 0.4174 11.00000 0.05 0.19 Q18 1 0.9994 0.1948 0.3579 11.00000 0.05 0.19 Q19 1 0.8277 0.6727 0.4180 11.00000 0.05 0.19 Q20 1 0.8550 0.2674 0.3514 11.00000 0.05 0.18 ; _shelx_res_checksum 60164