# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2016 ####################################################################### # # 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_I _database_code_depnum_ccdc_archive 'CCDC 1427664' _audit_update_record ; 2015-09-25 deposited with the CCDC. 2016-03-15 downloaded from the CCDC. ; _chemical_name_systematic ? _chemical_name_common YR1 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10.50 N P0.50' _chemical_formula_iupac ? _chemical_formula_weight 244.25 _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P n m a' _space_group_name_Hall '-P 2ac 2n' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' 'x-1/2, y, -z-1/2' _cell_length_a 15.8239(8) _cell_length_b 19.3822(10) _cell_length_c 7.8312(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2401.8(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9897 _cell_measurement_theta_min 2.5745 _cell_measurement_theta_max 33.7105 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'irregular rhombic shard' _exptl_crystal_colour 'translucent intense red-purple' _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.090 _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'BRUKER APEX II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 52792 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 36.37 _diffrn_reflns_theta_full 36.37 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 5933 _reflns_number_gt 4817 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_gt 0.1197 _refine_ls_wR_factor_ref 0.1312 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.944 _refine_ls_number_reflns 5933 _refine_ls_number_parameters 220 _refine_ls_number_restraints 84 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+2.2881P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.664 _refine_diff_density_min -0.439 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.30C (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.30C (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? 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 P P1 0.75166(2) 0.25 0.70796(5) 0.01177(8) Uani d . . S 1 . . N N1 0.73097(5) 0.31828(5) 0.57524(12) 0.01551(15) Uani d . . . 1 . . C C1 0.78364(6) 0.37605(5) 0.56738(14) 0.01674(17) Uani d . . D 1 . . C C2 0.86182(7) 0.38680(5) 0.64444(16) 0.01930(19) Uani d . . D 1 . . H H2 0.8875 0.3526 0.7141 0.023 Uiso calc . . R 1 . . C C3 0.90061(8) 0.45005(6) 0.61446(19) 0.0259(2) Uani d . . D 1 . . H H3 0.954 0.4594 0.6651 0.031 Uiso calc . . R 1 . . C C4 0.86254(10) 0.50049(6) 0.5109(2) 0.0315(3) Uani d . . D 1 . . H H4 0.8911 0.5429 0.4916 0.038 Uiso calc . . R 1 . . C C5 0.78470(10) 0.48976(6) 0.43676(19) 0.0309(3) Uani d . . D 1 . . H H5 0.7594 0.5243 0.3675 0.037 Uiso calc . . R 1 . . C C6 0.74351(8) 0.42661(6) 0.46580(15) 0.0224(2) Uani d . . D 1 . . C C7 0.66421(8) 0.39854(7) 0.41388(16) 0.0252(2) Uani d . . . 1 . . H H7 0.6234 0.421 0.3442 0.03 Uiso calc . . R 1 . . C C8 0.65696(6) 0.33344(6) 0.48201(14) 0.01941(19) Uani d . . . 1 . . C C9 0.58711(6) 0.28568(7) 0.46689(13) 0.0222(2) Uani d . . . 1 . . C C10A 0.50138(19) 0.31956(15) 0.4413(4) 0.0150(5) Uani d U P D 0.5 . 1 C C11A 0.46462(18) 0.38352(16) 0.4299(4) 0.0196(5) Uani d U P D 0.5 . 1 H H11A 0.497 0.4243 0.4451 0.024 Uiso calc . P R 0.5 . 1 C C12A 0.37616(17) 0.38676(17) 0.3945(4) 0.0233(5) Uani d U P D 0.5 . 1 H H12A 0.3503 0.4308 0.3853 0.028 Uiso calc . P R 0.5 . 1 C C13A 0.32692(17) 0.32946(17) 0.3733(4) 0.0225(5) Uani d U P D 0.5 . 1 H H13A 0.2685 0.3344 0.3483 0.027 Uiso calc . P R 0.5 . 1 C C10B 0.49675(19) 0.29989(15) 0.4390(4) 0.0145(5) Uani d U P D 0.5 . 2 C C11B 0.45529(18) 0.36234(16) 0.4242(4) 0.0201(5) Uani d U P D 0.5 . 2 H H11B 0.4847 0.4047 0.4384 0.024 Uiso calc . P R 0.5 . 2 C C12B 0.36632(18) 0.36140(17) 0.3866(4) 0.0245(5) Uani d U P D 0.5 . 2 H H12B 0.3374 0.4041 0.3742 0.029 Uiso calc . P R 0.5 . 2 C C13B 0.32206(16) 0.30181(17) 0.3681(4) 0.0223(4) Uani d U P D 0.5 . 2 H H13B 0.258(2) 0.2995(18) 0.336(5) 0.027 Uiso d . P . 0.5 A 2 C C14 0.36264(12) 0.2375(2) 0.3886(3) 0.0257(11) Uani d U P D 0.5 . . C C15 0.44973(12) 0.2397(2) 0.4239(2) 0.0201(10) Uani d U P D 0.5 . . C C16 0.65559(8) 0.25 0.83553(17) 0.0124(2) Uani d . . S 1 . . C C17 0.62012(7) 0.18788(5) 0.88889(14) 0.01672(17) Uani d . . . 1 . . H H17 0.646 0.1454 0.8584 0.02 Uiso calc . . R 1 . . C C18 0.54674(7) 0.18805(6) 0.98683(15) 0.0208(2) Uani d . . . 1 . . H H18 0.5225 0.1457 1.023 0.025 Uiso calc . . R 1 . . C C19 0.50898(10) 0.25 1.03167(19) 0.0214(3) Uani d . . S 1 . . H H19 0.4572 0.25 1.0931 0.026 Uiso calc . . SR 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 P1 0.01127(13) 0.01138(14) 0.01268(14) 0 -0.00024(11) 0 N1 0.0127(3) 0.0173(4) 0.0165(4) 0.0018(3) 0.0008(3) 0.0050(3) C1 0.0178(4) 0.0132(4) 0.0192(4) 0.0039(3) 0.0066(3) 0.0035(3) C2 0.0178(4) 0.0131(4) 0.0270(5) 0.0002(3) 0.0052(4) 0.0015(4) C3 0.0263(5) 0.0136(4) 0.0378(6) -0.0024(4) 0.0113(5) -0.0008(4) C4 0.0410(7) 0.0122(4) 0.0414(7) 0.0008(4) 0.0175(6) 0.0038(5) C5 0.0423(7) 0.0166(5) 0.0337(6) 0.0104(5) 0.0136(6) 0.0095(5) C6 0.0277(5) 0.0182(4) 0.0213(5) 0.0099(4) 0.0082(4) 0.0069(4) C7 0.0251(5) 0.0303(6) 0.0203(5) 0.0138(4) 0.0031(4) 0.0078(4) C8 0.0152(4) 0.0285(5) 0.0146(4) 0.0077(4) 0.0016(3) 0.0043(4) C9 0.0124(4) 0.0417(6) 0.0125(4) 0.0050(4) -0.0001(3) 0.0020(4) C10A 0.0143(7) 0.0177(9) 0.0130(7) 0.0013(7) 0.0006(6) 0.0003(8) C11A 0.0172(8) 0.0218(9) 0.0199(8) 0.0054(7) 0.0002(6) 0.0013(7) C12A 0.0187(8) 0.0283(9) 0.0230(8) 0.0075(7) 0.0004(6) 0.0013(8) C13A 0.0185(7) 0.0291(9) 0.0200(8) 0.0065(7) 0.0001(6) 0.0005(7) C10B 0.0138(7) 0.0169(9) 0.0129(7) 0.0015(7) -0.0002(6) 0.0010(7) C11B 0.0183(8) 0.0229(9) 0.0191(8) 0.0022(7) -0.0005(6) -0.0002(8) C12B 0.0221(8) 0.0282(9) 0.0231(8) 0.0053(8) 0.0001(7) 0.0019(8) C13B 0.0164(7) 0.0313(9) 0.0193(8) 0.0008(7) 0.0005(6) 0.0020(8) C14 0.0119(6) 0.053(3) 0.0127(7) -0.0032(9) 0.0008(5) 0.0019(9) C15 0.0131(6) 0.036(3) 0.0114(6) -0.0047(8) 0.0003(5) 0.0002(8) C16 0.0132(5) 0.0118(5) 0.0120(5) 0 0.0001(4) 0 C17 0.0196(4) 0.0125(4) 0.0180(4) -0.0010(3) 0.0021(3) 0.0017(3) C18 0.0211(4) 0.0231(5) 0.0181(4) -0.0068(4) 0.0028(3) 0.0043(4) C19 0.0158(6) 0.0348(8) 0.0137(6) 0 0.0025(5) 0 _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 P1 N1 . 1.7143(9) ? P1 N1 7_565 1.7143(9) ? P1 C16 . 1.8190(13) ? N1 C1 . 1.3972(14) ? N1 C8 . 1.4110(13) ? C1 C2 . 1.3922(16) ? C1 C6 . 1.4129(15) ? C2 C3 . 1.3910(15) ? C2 H2 . 0.95 ? C3 C4 . 1.406(2) ? C3 H3 . 0.95 ? C4 C5 . 1.377(2) ? C4 H4 . 0.95 ? C5 C6 . 1.4053(18) ? C5 H5 . 0.95 ? C6 C7 . 1.4269(19) ? C7 C8 . 1.3747(17) ? C7 H7 . 0.95 ? C8 C9 . 1.4467(17) ? C9 C9 7_565 1.383(3) ? C9 C10B . 1.472(3) ? C9 C10A . 1.520(3) ? C10A C11A . 1.372(4) ? C10A C15 7_565 1.417(5) ? C10A C15 . 1.755(5) ? C11A C12A . 1.428(4) ? C11A H11A . 0.95 ? C12A C13A . 1.367(4) ? C12A H12A . 0.95 ? C13A C14 7_565 1.421(5) ? C13A C14 . 1.874(5) ? C13A H13A . 0.95 ? C13A H13B . 1.27(3) ? C10B C15 7_565 1.076(4) ? C10B C11B . 1.382(4) ? C10B C15 . 1.388(5) ? C10B C10B 7_565 1.934(6) ? C11B C12B . 1.438(4) ? C11B C15 7_565 1.981(5) ? C11B H11B . 0.95 ? C12B C13B . 1.359(4) ? C12B C14 7_565 1.918(5) ? C12B H12B . 0.95 ? C13B C14 7_565 1.009(4) ? C13B C14 . 1.411(5) ? C13B C13B 7_565 2.008(7) ? C13B H13B . 1.05(3) ? C14 C14 7_565 0.485(8) ? C14 C13B 7_565 1.009(4) ? C14 C15 . 1.406(3) ? C14 C13A 7_565 1.421(5) ? C14 C15 7_565 1.473(3) ? C14 C12B 7_565 1.918(5) ? C15 C15 7_565 0.397(9) ? C15 C10B 7_565 1.076(4) ? C15 C10A 7_565 1.417(5) ? C15 C14 7_565 1.473(3) ? C15 C11B 7_565 1.981(5) ? C16 C17 . 1.3925(12) ? C16 C17 7_565 1.3926(12) ? C17 C18 . 1.3916(15) ? C17 H17 . 0.95 ? C18 C19 . 1.3864(14) ? C18 H18 . 0.95 ? C19 C18 7_565 1.3863(14) ? C19 H19 . 0.95 ? 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 N1 P1 N1 . 7_565 101.06(7) ? N1 P1 C16 . . 99.99(4) ? N1 P1 C16 7_565 . 99.99(4) ? C1 N1 C8 . . 107.78(9) ? C1 N1 P1 . . 122.10(7) ? C8 N1 P1 . . 129.27(8) ? C2 C1 N1 . . 129.12(9) ? C2 C1 C6 . . 122.65(10) ? N1 C1 C6 . . 108.22(10) ? C3 C2 C1 . . 116.80(11) ? C3 C2 H2 . . 121.6 ? C1 C2 H2 . . 121.6 ? C2 C3 C4 . . 121.41(13) ? C2 C3 H3 . . 119.3 ? C4 C3 H3 . . 119.3 ? C5 C4 C3 . . 121.42(12) ? C5 C4 H4 . . 119.3 ? C3 C4 H4 . . 119.3 ? C4 C5 C6 . . 118.56(12) ? C4 C5 H5 . . 120.7 ? C6 C5 H5 . . 120.7 ? C5 C6 C1 . . 119.13(12) ? C5 C6 C7 . . 133.94(12) ? C1 C6 C7 . . 106.93(10) ? C8 C7 C6 . . 108.22(10) ? C8 C7 H7 . . 125.9 ? C6 C7 H7 . . 125.9 ? C7 C8 N1 . . 108.83(11) ? C7 C8 C9 . . 128.26(10) ? N1 C8 C9 . . 122.91(10) ? C9 C9 C8 7_565 . 129.78(6) ? C9 C9 C10B 7_565 . 100.79(13) ? C8 C9 C10B . . 129.38(15) ? C9 C9 C10A 7_565 . 115.59(12) ? C8 C9 C10A . . 114.59(15) ? C10B C9 C10A . . 14.81(12) ? C11A C10A C15 . 7_565 118.8(3) ? C11A C10A C9 . . 141.0(3) ? C15 C10A C9 7_565 . 100.2(2) ? C11A C10A C15 . . 126.4(3) ? C15 C10A C15 7_565 . 7.61(17) ? C9 C10A C15 . . 92.59(18) ? C10A C11A C12A . . 117.9(3) ? C10A C11A H11A . . 121.1 ? C12A C11A H11A . . 121.1 ? C13A C12A C11A . . 123.1(3) ? C13A C12A H12A . . 118.4 ? C11A C12A H12A . . 118.4 ? C12A C13A C14 . 7_565 120.3(2) ? C12A C13A C14 . . 126.4(2) ? C14 C13A C14 7_565 . 6.04(11) ? C12A C13A H13A . . 119.8 ? C14 C13A H13A 7_565 . 119.8 ? C14 C13A H13A . . 113.8 ? C12A C13A H13B . . 152.7(16) ? C14 C13A H13B 7_565 . 86.8(16) ? C14 C13A H13B . . 80.8(16) ? H13A C13A H13B . . 33.1 ? C15 C10B C11B 7_565 . 106.7(3) ? C15 C10B C15 7_565 . 11.6(3) ? C11B C10B C15 . . 118.3(3) ? C15 C10B C9 7_565 . 123.7(3) ? C11B C10B C9 . . 129.6(2) ? C15 C10B C9 . . 112.1(2) ? C15 C10B C10B 7_565 7_565 44.4(2) ? C11B C10B C10B . 7_565 151.17(17) ? C15 C10B C10B . 7_565 32.88(16) ? C9 C10B C10B . 7_565 79.22(12) ? C10B C11B C12B . . 118.1(3) ? C10B C11B C15 . 7_565 31.35(15) ? C12B C11B C15 . 7_565 86.8(2) ? C10B C11B H11B . . 121.0 ? C12B C11B H11B . . 121.0 ? C15 C11B H11B 7_565 . 152.2 ? C13B C12B C11B . . 122.5(3) ? C13B C12B C14 . 7_565 30.17(14) ? C11B C12B C14 . 7_565 92.3(2) ? C13B C12B H12B . . 118.8 ? C11B C12B H12B . . 118.8 ? C14 C12B H12B 7_565 . 148.9 ? C14 C13B C12B 7_565 . 107.3(3) ? C14 C13B C14 7_565 . 13.0(2) ? C12B C13B C14 . . 120.3(2) ? C14 C13B C13B 7_565 7_565 41.0(2) ? C12B C13B C13B . 7_565 148.23(16) ? C14 C13B C13B . 7_565 27.97(15) ? C14 C13B H13B 7_565 . 129.(2) ? C12B C13B H13B . . 124.1(19) ? C14 C13B H13B . . 115.6(19) ? C13B C13B H13B 7_565 . 87.6(19) ? C14 C14 C13B 7_565 7_565 139.0(2) ? C14 C14 C15 7_565 . 88.2(2) ? C13B C14 C15 7_565 . 132.7(4) ? C14 C14 C13B 7_565 . 27.98(15) ? C13B C14 C13B 7_565 . 111.0(3) ? C15 C14 C13B . . 116.2(3) ? C14 C14 C13A 7_565 7_565 156.00(16) ? C13B C14 C13A 7_565 7_565 17.0(2) ? C15 C14 C13A . 7_565 115.8(3) ? C13B C14 C13A . 7_565 128.0(2) ? C14 C14 C15 7_565 7_565 72.6(2) ? C13B C14 C15 7_565 7_565 148.3(4) ? C15 C14 C15 . 7_565 15.6(3) ? C13B C14 C15 . 7_565 100.5(3) ? C13A C14 C15 7_565 7_565 131.4(3) ? C14 C14 C13A 7_565 . 17.97(11) ? C13B C14 C13A 7_565 . 121.1(3) ? C15 C14 C13A . . 106.2(3) ? C13B C14 C13A . . 10.04(15) ? C13A C14 C13A 7_565 . 138.0(2) ? C15 C14 C13A 7_565 . 90.5(3) ? C14 C14 C12B 7_565 7_565 178.18(11) ? C13B C14 C12B 7_565 7_565 42.6(2) ? C15 C14 C12B . 7_565 90.2(3) ? C13B C14 C12B . 7_565 153.6(2) ? C13A C14 C12B 7_565 7_565 25.62(16) ? C15 C14 C12B 7_565 7_565 105.8(2) ? C13A C14 C12B . 7_565 163.62(18) ? C15 C15 C10B 7_565 7_565 135.6(2) ? C15 C15 C10B 7_565 . 32.87(16) ? C10B C15 C10B 7_565 . 102.7(3) ? C15 C15 C14 7_565 . 91.8(2) ? C10B C15 C14 7_565 . 132.6(4) ? C10B C15 C14 . . 124.6(3) ? C15 C15 C10A 7_565 7_565 144.21(17) ? C10B C15 C10A 7_565 7_565 8.7(2) ? C10B C15 C10A . 7_565 111.34(18) ? C14 C15 C10A . 7_565 124.0(3) ? C15 C15 C14 7_565 7_565 72.6(2) ? C10B C15 C14 7_565 7_565 151.8(4) ? C10B C15 C14 . 7_565 105.4(3) ? C14 C15 C14 . 7_565 19.2(3) ? C10A C15 C14 7_565 7_565 143.2(3) ? C15 C15 C10A 7_565 . 28.17(13) ? C10B C15 C10A 7_565 . 107.4(2) ? C10B C15 C10A . . 4.7(2) ? C14 C15 C10A . . 119.9(3) ? C10A C15 C10A 7_565 . 116.0(2) ? C14 C15 C10A 7_565 . 100.7(3) ? C15 C15 C11B 7_565 7_565 177.45(10) ? C10B C15 C11B 7_565 7_565 41.9(2) ? C10B C15 C11B . 7_565 144.6(2) ? C14 C15 C11B . 7_565 90.7(3) ? C10A C15 C11B 7_565 7_565 33.27(17) ? C14 C15 C11B 7_565 7_565 109.9(2) ? C10A C15 C11B . 7_565 149.30(18) ? C17 C16 C17 . 7_565 119.67(13) ? C17 C16 P1 . . 120.11(6) ? C17 C16 P1 7_565 . 120.11(6) ? C18 C17 C16 . . 119.98(10) ? C18 C17 H17 . . 120.0 ? C16 C17 H17 . . 120.0 ? C19 C18 C17 . . 120.08(10) ? C19 C18 H18 . . 120.0 ? C17 C18 H18 . . 120.0 ? C18 C19 C18 7_565 . 120.02(14) ? C18 C19 H19 7_565 . 120.0 ? C18 C19 H19 . . 120.0 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 P1 N1 C1 7_565 . . . -136.59(7) ? C16 P1 N1 C1 . . . . 121.06(8) ? N1 P1 N1 C8 7_565 . . . 55.27(11) ? C16 P1 N1 C8 . . . . -47.08(10) ? C8 N1 C1 C2 . . . . 177.40(11) ? P1 N1 C1 C2 . . . . 7.02(16) ? C8 N1 C1 C6 . . . . -1.44(12) ? P1 N1 C1 C6 . . . . -171.83(8) ? N1 C1 C2 C3 . . . . -179.91(11) ? C6 C1 C2 C3 . . . . -1.21(16) ? C1 C2 C3 C4 . . . . -0.15(18) ? C2 C3 C4 C5 . . . . 0.9(2) ? C3 C4 C5 C6 . . . . -0.4(2) ? C4 C5 C6 C1 . . . . -0.95(18) ? C4 C5 C6 C7 . . . . 178.86(13) ? C2 C1 C6 C5 . . . . 1.80(17) ? N1 C1 C6 C5 . . . . -179.26(10) ? C2 C1 C6 C7 . . . . -178.06(10) ? N1 C1 C6 C7 . . . . 0.87(12) ? C5 C6 C7 C8 . . . . -179.79(13) ? C1 C6 C7 C8 . . . . 0.04(13) ? C6 C7 C8 N1 . . . . -0.93(13) ? C6 C7 C8 C9 . . . . 178.78(11) ? C1 N1 C8 C7 . . . . 1.48(12) ? P1 N1 C8 C7 . . . . 170.95(8) ? C1 N1 C8 C9 . . . . -178.25(10) ? P1 N1 C8 C9 . . . . -8.78(16) ? C7 C8 C9 C9 . . . 7_565 149.82(9) ? N1 C8 C9 C9 . . . 7_565 -30.50(13) ? C7 C8 C9 C10B . . . . -26.9(2) ? N1 C8 C9 C10B . . . . 152.77(19) ? C7 C8 C9 C10A . . . . -27.9(2) ? N1 C8 C9 C10A . . . . 151.77(16) ? C9 C9 C10A C11A 7_565 . . . -179.8(4) ? C8 C9 C10A C11A . . . . -1.7(5) ? C10B C9 C10A C11A . . . . -178.7(12) ? C9 C9 C10A C15 7_565 . . 7_565 -0.6(2) ? C8 C9 C10A C15 . . . 7_565 177.42(14) ? C10B C9 C10A C15 . . . 7_565 0.4(7) ? C9 C9 C10A C15 7_565 . . . -0.51(18) ? C8 C9 C10A C15 . . . . 177.56(11) ? C10B C9 C10A C15 . . . . 0.6(8) ? C15 C10A C11A C12A 7_565 . . . -2.3(4) ? C9 C10A C11A C12A . . . . 176.7(3) ? C15 C10A C11A C12A . . . . -2.3(5) ? C10A C11A C12A C13A . . . . 0.6(5) ? C11A C12A C13A C14 . . . 7_565 1.0(4) ? C11A C12A C13A C14 . . . . 1.0(4) ? C9 C9 C10B C15 7_565 . . 7_565 -0.3(3) ? C8 C9 C10B C15 . . . 7_565 177.1(2) ? C10A C9 C10B C15 . . . 7_565 -179.3(11) ? C9 C9 C10B C11B 7_565 . . . -179.1(3) ? C8 C9 C10B C11B . . . . -1.7(4) ? C10A C9 C10B C11B . . . . 1.9(6) ? C9 C9 C10B C15 7_565 . . . -0.2(2) ? C8 C9 C10B C15 . . . . 177.23(15) ? C10A C9 C10B C15 . . . . -179.2(10) ? C9 C9 C10B C10B 7_565 . . 7_565 0 ? C8 C9 C10B C10B . . . 7_565 177.45(17) ? C10A C9 C10B C10B . . . 7_565 -179.0(8) ? C15 C10B C11B C12B 7_565 . . . -2.7(4) ? C15 C10B C11B C12B . . . . -2.6(4) ? C9 C10B C11B C12B . . . . 176.3(3) ? C10B C10B C11B C12B 7_565 . . . -2.0(6) ? C15 C10B C11B C15 . . . 7_565 0.11(4) ? C9 C10B C11B C15 . . . 7_565 179.0(5) ? C10B C10B C11B C15 7_565 . . 7_565 0.7(2) ? C10B C11B C12B C13B . . . . 1.1(5) ? C15 C11B C12B C13B 7_565 . . . -0.4(3) ? C10B C11B C12B C14 . . . 7_565 1.8(3) ? C15 C11B C12B C14 7_565 . . 7_565 0.37(15) ? C11B C12B C13B C14 . . . 7_565 1.4(4) ? C11B C12B C13B C14 . . . . 1.1(4) ? C14 C12B C13B C14 7_565 . . . -0.35(4) ? C11B C12B C13B C13B . . . 7_565 -0.2(5) ? C14 C12B C13B C13B 7_565 . . 7_565 -1.6(2) ? C12B C13B C14 C14 . . . 7_565 1.46(19) ? C13B C13B C14 C14 7_565 . . 7_565 180.004(2) ? C14 C13B C14 C13B 7_565 . . 7_565 179.996(2) ? C12B C13B C14 C13B . . . 7_565 -178.54(19) ? C14 C13B C14 C15 7_565 . . . -3.0(4) ? C12B C13B C14 C15 . . . . -1.6(4) ? C13B C13B C14 C15 7_565 . . . 177.0(4) ? C14 C13B C14 C13A 7_565 . . 7_565 178.9(2) ? C12B C13B C14 C13A . . . 7_565 -179.6(3) ? C13B C13B C14 C13A 7_565 . . 7_565 -1.1(2) ? C14 C13B C14 C15 7_565 . . 7_565 -2.6(3) ? C12B C13B C14 C15 . . . 7_565 -1.2(3) ? C13B C13B C14 C15 7_565 . . 7_565 177.4(3) ? C14 C13B C14 C13A 7_565 . . . 3.7(8) ? C12B C13B C14 C13A . . . . 5.1(8) ? C13B C13B C14 C13A 7_565 . . . -176.3(8) ? C14 C13B C14 C12B 7_565 . . 7_565 -178.0(3) ? C12B C13B C14 C12B . . . 7_565 -176.5(4) ? C13B C13B C14 C12B 7_565 . . 7_565 2.0(3) ? C12A C13A C14 C14 . . . 7_565 0.0(2) ? C12A C13A C14 C13B . . . 7_565 -178.5(3) ? C14 C13A C14 C13B 7_565 . . 7_565 -178.4(3) ? C12A C13A C14 C15 . . . . -0.7(3) ? C14 C13A C14 C15 7_565 . . . -0.7(4) ? C12A C13A C14 C13B . . . . -174.5(11) ? C14 C13A C14 C13B 7_565 . . . -174.4(11) ? C12A C13A C14 C13A . . . 7_565 180.0(2) ? C14 C13A C14 C13A 7_565 . . 7_565 179.994(2) ? C12A C13A C14 C15 . . . 7_565 -0.7(3) ? C14 C13A C14 C15 7_565 . . 7_565 -0.6(4) ? C12A C13A C14 C12B . . . 7_565 -177.1(5) ? C14 C13A C14 C12B 7_565 . . 7_565 -177.0(4) ? C11B C10B C15 C15 . . . 7_565 -0.55(17) ? C9 C10B C15 C15 . . . 7_565 -179.6(4) ? C10B C10B C15 C15 7_565 . . 7_565 -179.992(2) ? C15 C10B C15 C10B 7_565 . . 7_565 179.9920(10) ? C11B C10B C15 C10B . . . 7_565 179.45(17) ? C9 C10B C15 C10B . . . 7_565 0.4(4) ? C15 C10B C15 C14 7_565 . . . 2.8(4) ? C11B C10B C15 C14 . . . . 2.2(4) ? C9 C10B C15 C14 . . . . -176.85(18) ? C10B C10B C15 C14 7_565 . . . -177.2(4) ? C15 C10B C15 C10A 7_565 . . 7_565 -179.7(3) ? C11B C10B C15 C10A . . . 7_565 179.7(3) ? C9 C10B C15 C10A . . . 7_565 0.7(2) ? C10B C10B C15 C10A 7_565 . . 7_565 0.3(3) ? C15 C10B C15 C14 7_565 . . 7_565 2.2(3) ? C11B C10B C15 C14 . . . 7_565 1.7(3) ? C9 C10B C15 C14 . . . 7_565 -177.36(19) ? C10B C10B C15 C14 7_565 . . 7_565 -177.7(3) ? C15 C10B C15 C10A 7_565 . . . -3.(2) ? C11B C10B C15 C10A . . . . -3.(2) ? C9 C10B C15 C10A . . . . 178.(3) ? C10B C10B C15 C10A 7_565 . . . 177.(2) ? C15 C10B C15 C11B 7_565 . . 7_565 179.41(18) ? C11B C10B C15 C11B . . . 7_565 178.9(3) ? C9 C10B C15 C11B . . . 7_565 -0.2(5) ? C10B C10B C15 C11B 7_565 . . 7_565 -0.58(18) ? C14 C14 C15 C15 7_565 . . 7_565 0 ? C13B C14 C15 C15 7_565 . . 7_565 177.6(3) ? C13B C14 C15 C15 . . . 7_565 1.41(19) ? C13A C14 C15 C15 7_565 . . 7_565 179.71(18) ? C13A C14 C15 C15 . . . 7_565 0.20(13) ? C12B C14 C15 C15 7_565 . . 7_565 179.18(11) ? C14 C14 C15 C10B 7_565 . . 7_565 -177.8(3) ? C13B C14 C15 C10B 7_565 . . 7_565 -0.2(5) ? C13B C14 C15 C10B . . . 7_565 -176.4(3) ? C13A C14 C15 C10B 7_565 . . 7_565 1.9(4) ? C15 C14 C15 C10B 7_565 . . 7_565 -177.8(3) ? C13A C14 C15 C10B . . . 7_565 -177.6(3) ? C12B C14 C15 C10B 7_565 . . 7_565 1.4(4) ? C14 C14 C15 C10B 7_565 . . . -1.5(2) ? C13B C14 C15 C10B 7_565 . . . 176.1(3) ? C13B C14 C15 C10B . . . . -0.1(3) ? C13A C14 C15 C10B 7_565 . . . 178.2(2) ? C15 C14 C15 C10B 7_565 . . . -1.5(2) ? C13A C14 C15 C10B . . . . -1.3(3) ? C12B C14 C15 C10B 7_565 . . . 177.7(2) ? C14 C14 C15 C10A 7_565 . . 7_565 -178.7(2) ? C13B C14 C15 C10A 7_565 . . 7_565 -1.1(4) ? C13B C14 C15 C10A . . . 7_565 -177.3(2) ? C13A C14 C15 C10A 7_565 . . 7_565 1.0(3) ? C15 C14 C15 C10A 7_565 . . 7_565 -178.7(2) ? C13A C14 C15 C10A . . . 7_565 -178.5(2) ? C12B C14 C15 C10A 7_565 . . 7_565 0.5(3) ? C13B C14 C15 C14 7_565 . . 7_565 177.6(3) ? C13B C14 C15 C14 . . . 7_565 1.42(19) ? C13A C14 C15 C14 7_565 . . 7_565 179.71(18) ? C15 C14 C15 C14 7_565 . . 7_565 0 ? C13A C14 C15 C14 . . . 7_565 0.21(13) ? C12B C14 C15 C14 7_565 . . 7_565 179.18(11) ? C14 C14 C15 C10A 7_565 . . . -1.01(17) ? C13B C14 C15 C10A 7_565 . . . 176.6(3) ? C13B C14 C15 C10A . . . . 0.4(3) ? C13A C14 C15 C10A 7_565 . . . 178.7(2) ? C15 C14 C15 C10A 7_565 . . . -1.00(17) ? C13A C14 C15 C10A . . . . -0.8(2) ? C12B C14 C15 C10A 7_565 . . . 178.18(19) ? C14 C14 C15 C11B 7_565 . . 7_565 -179.56(11) ? C13B C14 C15 C11B 7_565 . . 7_565 -2.0(4) ? C13B C14 C15 C11B . . . 7_565 -178.1(2) ? C13A C14 C15 C11B 7_565 . . 7_565 0.1(2) ? C15 C14 C15 C11B 7_565 . . 7_565 -179.56(11) ? C13A C14 C15 C11B . . . 7_565 -179.35(16) ? C12B C14 C15 C11B 7_565 . . 7_565 -0.38(15) ? C11A C10A C15 C15 . . . 7_565 0.41(18) ? C9 C10A C15 C15 . . . 7_565 -179.0(3) ? C11A C10A C15 C10B . . . 7_565 -179.9(4) ? C15 C10A C15 C10B 7_565 . . 7_565 179.7(3) ? C9 C10A C15 C10B . . . 7_565 0.65(19) ? C11A C10A C15 C10B . . . . 178.(3) ? C15 C10A C15 C10B 7_565 . . . 177.(3) ? C9 C10A C15 C10B . . . . -2.(3) ? C11A C10A C15 C14 . . . . 2.5(4) ? C15 C10A C15 C14 7_565 . . . 2.1(4) ? C9 C10A C15 C14 . . . . -176.90(17) ? C11A C10A C15 C10A . . . 7_565 -179.60(18) ? C15 C10A C15 C10A 7_565 . . 7_565 179.993(2) ? C9 C10A C15 C10A . . . 7_565 1.0(3) ? C11A C10A C15 C14 . . . 7_565 2.2(3) ? C15 C10A C15 C14 7_565 . . 7_565 1.8(3) ? C9 C10A C15 C14 . . . 7_565 -177.23(16) ? C11A C10A C15 C11B . . . 7_565 179.7(2) ? C15 C10A C15 C11B 7_565 . . 7_565 179.3(2) ? C9 C10A C15 C11B . . . 7_565 0.3(4) ? N1 P1 C16 C17 . . . . 143.56(10) ? N1 P1 C16 C17 7_565 . . . 40.33(11) ? N1 P1 C16 C17 . . . 7_565 -40.33(11) ? N1 P1 C16 C17 7_565 . . 7_565 -143.56(10) ? C17 C16 C17 C18 7_565 . . . 3.7(2) ? P1 C16 C17 C18 . . . . 179.84(9) ? C16 C17 C18 C19 . . . . -0.14(18) ? C17 C18 C19 C18 . . . 7_565 -3.5(2) ? ####################################################################### # # 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_I _database_code_depnum_ccdc_archive 'CCDC 1427665' _audit_update_record ; 2015-09-25 deposited with the CCDC. 2016-03-15 downloaded from the CCDC. ; _chemical_name_systematic ? _chemical_name_common YR5 _chemical_formula_moiety ? _chemical_formula_sum 'C34.50 H21.50 Cl1.50 N2 O P' _chemical_formula_iupac ? _chemical_formula_weight 564.18 _chemical_melting_point ? _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.925(5) _cell_length_b 12.375(6) _cell_length_c 18.662(9) _cell_angle_alpha 87.764(14) _cell_angle_beta 76.460(9) _cell_angle_gamma 83.562(10) _cell_volume 2660.(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9914 _cell_measurement_theta_min 2.2485 _cell_measurement_theta_max 29.5586 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour 'translucent intense red' _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'fine-focus tube' _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'TRIUMPH curved-crystal' _diffrn_measurement_device_type 'BRUKER APEX II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 55541 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 29.59 _diffrn_reflns_theta_full 29.59 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 14874 _reflns_number_gt 11710 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_gt 0.1143 _refine_ls_wR_factor_ref 0.1286 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.041 _refine_ls_number_reflns 14874 _refine_ls_number_parameters 758 _refine_ls_number_restraints 60 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+1.0398P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.528 _refine_diff_density_min -0.568 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.30C (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.30C (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? 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 P P1 -0.08528(3) 0.13567(3) 0.70513(2) 0.01274(8) Uani d . . . 1.0 . . C C1 -0.04190(15) -0.03535(12) 0.60671(8) 0.0179(3) Uani d . . . 1.0 . . N N1 -0.00300(12) 0.04358(10) 0.64529(7) 0.0150(2) Uani d . . . 1.0 . . O O1 -0.21052(10) 0.13372(9) 0.71123(6) 0.0184(2) Uani d . . . 1.0 . . C C2 -0.15311(17) -0.04949(13) 0.60069(9) 0.0223(3) Uani d . . . 1.0 . . H H2 -0.2189 -0.0035 0.6253 0.027 Uiso calc . . R 1.0 . . P P2 0.76834(3) 0.27729(3) 0.069121(19) 0.01010(8) Uani d . . . 1.0 . . N N2 -0.03822(11) 0.25518(10) 0.67135(7) 0.0135(2) Uani d . . . 1.0 . . O O2 0.89252(9) 0.27210(8) 0.06755(6) 0.0142(2) Uani d . . . 1.0 . . N N3 0.68651(11) 0.31635(10) 0.15220(6) 0.0116(2) Uani d . . . 1.0 . . C C3 -0.16325(19) -0.13472(14) 0.55660(10) 0.0283(4) Uani d . . . 1.0 . . H H3 -0.238 -0.1469 0.551 0.034 Uiso calc . . R 1.0 . . N N4 0.72654(10) 0.37310(9) 0.01091(6) 0.0105(2) Uani d . . . 1.0 . . C C4 -0.06623(19) -0.20296(14) 0.52030(9) 0.0291(4) Uani d . . . 1.0 . . H H4 -0.0765 -0.2602 0.4907 0.035 Uiso calc . . R 1.0 . . C C5 0.04305(19) -0.18826(13) 0.52686(9) 0.0269(4) Uani d . . . 1.0 . . H H5 0.1083 -0.2347 0.502 0.032 Uiso calc . . R 1.0 . . C C6 0.05726(16) -0.10326(13) 0.57095(8) 0.0206(3) Uani d . . . 1.0 . . C C7 0.15616(16) -0.06558(13) 0.58835(9) 0.0209(3) Uani d . . . 1.0 . . H H7 0.2342 -0.0967 0.5721 0.025 Uiso calc . . R 1.0 . . C C8 0.11900(14) 0.02358(12) 0.63269(8) 0.0159(3) Uani d . . . 1.0 . . C C9 0.18878(14) 0.09159(12) 0.66194(8) 0.0152(3) Uani d . . . 1.0 . . C C10 0.29968(14) 0.04907(13) 0.68059(8) 0.0174(3) Uani d . . . 1.0 . . C C19 0.34494(14) 0.13861(13) 0.70338(8) 0.0177(3) Uani d . . . 1.0 . . C C18 0.26899(14) 0.23458(13) 0.70228(8) 0.0158(3) Uani d . . . 1.0 . . C C17 0.29925(15) 0.33007(13) 0.72490(8) 0.0189(3) Uani d . . . 1.0 . . H H17 0.2494 0.3959 0.7264 0.023 Uiso calc . . R 1.0 . . C C16 0.40701(15) 0.32748(15) 0.74583(9) 0.0230(3) Uani d . . . 1.0 . . H H16 0.4287 0.3933 0.7604 0.028 Uiso calc . . R 1.0 . . C C15 0.48140(16) 0.23333(16) 0.74581(9) 0.0250(4) Uani d . . . 1.0 . . H H15 0.5526 0.2353 0.76 0.03 Uiso calc . . R 1.0 . . C C14 0.45076(15) 0.13341(15) 0.72438(9) 0.0217(3) Uani d . . . 1.0 . . C C13 0.51473(15) 0.02867(16) 0.72176(9) 0.0263(4) Uani d . . . 1.0 . . H H13 0.5882 0.0199 0.734 0.032 Uiso calc . . R 1.0 . . C C12 0.46944(17) -0.05980(16) 0.70136(10) 0.0278(4) Uani d . . . 1.0 . . H H12 0.5128 -0.1292 0.7008 0.033 Uiso calc . . R 1.0 . . C C11 0.36099(15) -0.05249(14) 0.68112(9) 0.0222(3) Uani d . . . 1.0 . . H H11 0.3316 -0.1155 0.6684 0.027 Uiso calc . . R 1.0 . . C C20 0.17072(13) 0.20281(12) 0.67484(8) 0.0144(3) Uani d . . . 1.0 . . C C22 0.08222(14) 0.38747(12) 0.63899(8) 0.0165(3) Uani d . . . 1.0 . . H H22 0.1493 0.4254 0.6292 0.02 Uiso calc . . R 1.0 . . C C21 0.07691(13) 0.28123(12) 0.66227(8) 0.0137(3) Uani d . . . 1.0 . . C C23 -0.03085(15) 0.43103(12) 0.63201(8) 0.0169(3) Uani d . . . 1.0 . . C C24 -0.07632(17) 0.53390(13) 0.61067(10) 0.0236(3) Uani d . . . 1.0 . . H H24 -0.0278 0.5907 0.5967 0.028 Uiso calc . . R 1.0 . . C C25 -0.19228(17) 0.55090(14) 0.61033(10) 0.0267(4) Uani d . . . 1.0 . . H H25 -0.224 0.6203 0.5965 0.032 Uiso calc . . R 1.0 . . C C34 -0.02251(13) 0.19703(12) 0.83034(8) 0.0143(3) Uani d . . . 1.0 . . H H34 -0.0447 0.2698 0.8171 0.017 Uiso calc . . R 1.0 . . C C33 0.02132(14) 0.17554(12) 0.89288(8) 0.0165(3) Uani d . . . 1.0 . . H H33 0.0303 0.234 0.9219 0.02 Uiso calc . . R 1.0 . . C C32 0.05209(14) 0.06887(13) 0.91309(8) 0.0173(3) Uani d . . . 1.0 . . H H32 0.0828 0.0547 0.9555 0.021 Uiso calc . . R 1.0 . . C C31 0.03796(15) -0.01687(13) 0.87137(9) 0.0190(3) Uani d . . . 1.0 . . H H31 0.0569 -0.0897 0.886 0.023 Uiso calc . . R 1.0 . . C C30 -0.00389(15) 0.00403(12) 0.80811(8) 0.0177(3) Uani d . . . 1.0 . . H H30 -0.0122 -0.0546 0.779 0.021 Uiso calc . . R 1.0 . . C C29 -0.03375(13) 0.11098(12) 0.78723(8) 0.0127(3) Uani d . . . 1.0 . . C C28 -0.10507(14) 0.34826(12) 0.65204(8) 0.0142(3) Uani d . . . 1.0 . . C C27 -0.22220(14) 0.36450(13) 0.65128(8) 0.0178(3) Uani d . . . 1.0 . . H H27 -0.2712 0.308 0.6646 0.021 Uiso calc . . R 1.0 . . C C26 -0.26407(16) 0.46721(14) 0.63010(9) 0.0229(3) Uani d . . . 1.0 . . H H26 -0.3436 0.481 0.629 0.027 Uiso calc . . R 1.0 . . C C37 0.84735(15) 0.33539(14) 0.30043(9) 0.0208(3) Uani d . . . 1.0 . . H H37 0.922 0.3251 0.311 0.025 Uiso calc . . R 1.0 . . C C36 0.83633(14) 0.31796(13) 0.22925(8) 0.0173(3) Uani d . . . 1.0 . . H H36 0.9022 0.2976 0.1907 0.021 Uiso calc . . R 1.0 . . C C35 0.72508(13) 0.33150(11) 0.21678(8) 0.0128(3) Uani d . . . 1.0 . . C C38 0.75005(16) 0.36792(14) 0.35698(9) 0.0227(3) Uani d . . . 1.0 . . H H38 0.7601 0.3796 0.405 0.027 Uiso calc . . R 1.0 . . C C39 0.63996(15) 0.38311(14) 0.34373(8) 0.0210(3) Uani d . . . 1.0 . . H H39 0.5748 0.4062 0.382 0.025 Uiso calc . . R 1.0 . . C C40 0.62599(14) 0.36386(12) 0.27291(8) 0.0148(3) Uani d . . . 1.0 . . C C41 0.52694(14) 0.36789(12) 0.24132(8) 0.0154(3) Uani d . . . 1.0 . . H H41 0.4486 0.3876 0.2663 0.019 Uiso calc . . R 1.0 . . C C42 0.56473(12) 0.33835(11) 0.16887(8) 0.0122(3) Uani d . . . 1.0 . . C C43 0.49452(13) 0.32517(11) 0.11646(8) 0.0120(3) Uani d . . . 1.0 . . C C44 0.37730(13) 0.29017(11) 0.14240(8) 0.0126(3) Uani d . . . 1.0 . . C C45 0.31346(14) 0.25307(12) 0.20848(8) 0.0161(3) Uani d . . . 1.0 . . H H45 0.3442 0.2479 0.2512 0.019 Uiso calc . . R 1.0 . . C C46 0.20101(14) 0.22276(13) 0.21138(9) 0.0189(3) Uani d . . . 1.0 . . H H46 0.1572 0.1966 0.2567 0.023 Uiso calc . . R 1.0 . . C C54 0.51534(12) 0.34386(11) 0.04046(8) 0.0113(3) Uani d . . . 1.0 . . C C53 0.32897(13) 0.29377(11) 0.08022(8) 0.0126(3) Uani d . . . 1.0 . . C C52 0.40934(13) 0.32480(11) 0.01637(8) 0.0123(3) Uani d . . . 1.0 . . C C51 0.37441(14) 0.32924(12) -0.04948(8) 0.0169(3) Uani d . . . 1.0 . . H H51 0.4258 0.3481 -0.0941 0.02 Uiso calc . . R 1.0 . . C C50 0.26071(15) 0.30524(13) -0.04936(9) 0.0197(3) Uani d . . . 1.0 . . H H50 0.2367 0.3102 -0.0946 0.024 Uiso calc . . R 1.0 . . C C49 0.18386(14) 0.27510(13) 0.01357(9) 0.0180(3) Uani d . . . 1.0 . . H H49 0.1082 0.2603 0.0115 0.022 Uiso calc . . R 1.0 . . C C48 0.21821(13) 0.26630(12) 0.08158(8) 0.0148(3) Uani d . . . 1.0 . . C C47 0.15350(14) 0.23013(12) 0.15044(9) 0.0175(3) Uani d . . . 1.0 . . H H47 0.0773 0.2109 0.1546 0.021 Uiso calc . . R 1.0 . . C C55 0.61833(13) 0.37712(11) -0.00938(8) 0.0115(3) Uani d . . . 1.0 . . C C56 0.63177(13) 0.41794(11) -0.08014(8) 0.0131(3) Uani d . . . 1.0 . . H H56 0.5728 0.4289 -0.107 0.016 Uiso calc . . R 1.0 . . C C57 0.74917(13) 0.44116(11) -0.10663(8) 0.0124(3) Uani d . . . 1.0 . . C C58 0.81073(14) 0.48333(12) -0.17374(8) 0.0155(3) Uani d . . . 1.0 . . H H58 0.7743 0.4993 -0.2136 0.019 Uiso calc . . R 1.0 . . C C59 0.92501(14) 0.50099(12) -0.18041(8) 0.0166(3) Uani d . . . 1.0 . . H H59 0.9676 0.5289 -0.2255 0.02 Uiso calc . . R 1.0 . . C C68 0.66746(14) 0.08388(12) 0.10240(9) 0.0173(3) Uani d . . . 1.0 . . H H68 0.6605 0.0993 0.1528 0.021 Uiso calc . . R 1.0 . . C C67 0.62894(16) -0.01042(13) 0.08298(10) 0.0230(3) Uani d . . . 1.0 . . H H67 0.5951 -0.0592 0.1203 0.028 Uiso calc . . R 1.0 . . C C66 0.63966(15) -0.03347(13) 0.00937(10) 0.0223(3) Uani d . . . 1.0 . . H H66 0.6124 -0.0976 -0.0035 0.027 Uiso calc . . R 1.0 . . C C65 0.69020(15) 0.03686(13) -0.04570(9) 0.0208(3) Uani d . . . 1.0 . . H H65 0.6984 0.0202 -0.0961 0.025 Uiso calc . . R 1.0 . . C C64 0.72863(14) 0.13150(12) -0.02701(8) 0.0161(3) Uani d . . . 1.0 . . H H64 0.7631 0.1797 -0.0646 0.019 Uiso calc . . R 1.0 . . C C63 0.71652(13) 0.15580(11) 0.04726(8) 0.0121(3) Uani d . . . 1.0 . . C C62 0.80715(13) 0.41507(11) -0.04937(8) 0.0116(3) Uani d . . . 1.0 . . C C61 0.92132(13) 0.43521(11) -0.05498(8) 0.0140(3) Uani d . . . 1.0 . . H H61 0.958 0.4201 -0.0151 0.017 Uiso calc . . R 1.0 . . C C60 0.97952(14) 0.47839(12) -0.12149(8) 0.0165(3) Uani d . . . 1.0 . . H H60 1.0577 0.4929 -0.1272 0.02 Uiso calc . . R 1.0 . . C C69A 0.4680(13) 0.2442(10) 0.5372(8) 0.048(3) Uani d U P . 0.353(11) A 1 H H69A 0.4249 0.2141 0.585 0.058 Uiso calc . P R 0.353(11) A 1 Cl Cl1A 0.6026(6) 0.2738(11) 0.5452(4) 0.116(3) Uani d U P . 0.353(11) A 1 Cl Cl2A 0.3936(7) 0.3816(5) 0.5175(3) 0.099(2) Uani d U P . 0.353(11) A 1 Cl Cl3A 0.4746(6) 0.1616(8) 0.4718(6) 0.080(2) Uani d U P . 0.353(11) A 1 C C69B 0.4673(4) 0.2638(4) 0.5407(3) 0.0201(9) Uani d U P . 0.647(11) A 2 H H69B 0.4278 0.2472 0.5928 0.024 Uiso calc . P R 0.647(11) A 2 Cl Cl1B 0.60382(16) 0.29817(19) 0.54175(12) 0.0406(6) Uani d U P . 0.647(11) A 2 Cl Cl2B 0.37895(16) 0.3611(3) 0.50835(14) 0.0590(7) Uani d U P . 0.647(11) A 2 Cl Cl3B 0.4835(4) 0.1416(4) 0.4900(3) 0.0852(14) Uani d U P . 0.647(11) 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.01375(19) 0.01315(17) 0.01263(17) -0.00264(14) -0.00532(14) 0.00102(12) C1 0.0298(9) 0.0140(6) 0.0126(6) -0.0047(6) -0.0095(6) 0.0017(5) N1 0.0178(7) 0.0146(6) 0.0142(6) -0.0023(5) -0.0067(5) -0.0012(4) O1 0.0157(6) 0.0198(5) 0.0226(6) -0.0038(4) -0.0093(4) 0.0005(4) C2 0.0299(9) 0.0198(7) 0.0217(8) -0.0069(7) -0.0134(7) 0.0017(6) P2 0.00865(17) 0.01030(16) 0.01126(16) -0.00150(13) -0.00200(13) 0.00065(12) N2 0.0129(6) 0.0133(5) 0.0149(6) -0.0008(5) -0.0054(5) 0.0019(4) O2 0.0097(5) 0.0166(5) 0.0162(5) -0.0019(4) -0.0027(4) 0.0020(4) N3 0.0091(6) 0.0152(5) 0.0113(5) -0.0013(4) -0.0034(4) -0.0009(4) C3 0.0462(12) 0.0240(8) 0.0225(8) -0.0155(8) -0.0187(8) 0.0032(6) N4 0.0087(6) 0.0108(5) 0.0125(5) -0.0029(4) -0.0030(4) 0.0018(4) C4 0.0548(13) 0.0204(8) 0.0175(8) -0.0123(8) -0.0157(8) 0.0010(6) C5 0.0475(12) 0.0170(7) 0.0164(7) -0.0030(7) -0.0077(7) -0.0018(6) C6 0.0340(10) 0.0150(7) 0.0136(7) -0.0033(6) -0.0069(6) 0.0009(5) C7 0.0272(9) 0.0176(7) 0.0165(7) 0.0015(6) -0.0043(6) -0.0007(6) C8 0.0186(8) 0.0153(6) 0.0132(6) 0.0000(6) -0.0038(6) 0.0027(5) C9 0.0146(7) 0.0173(7) 0.0126(6) 0.0006(6) -0.0022(5) 0.0011(5) C10 0.0157(7) 0.0213(7) 0.0133(6) 0.0002(6) -0.0010(5) 0.0037(5) C19 0.0133(7) 0.0248(8) 0.0140(6) -0.0022(6) -0.0020(5) 0.0048(6) C18 0.0131(7) 0.0210(7) 0.0130(6) -0.0032(6) -0.0026(5) 0.0035(5) C17 0.0188(8) 0.0231(8) 0.0161(7) -0.0061(6) -0.0052(6) 0.0033(6) C16 0.0205(8) 0.0320(9) 0.0189(7) -0.0112(7) -0.0064(6) 0.0049(6) C15 0.0177(8) 0.0400(10) 0.0199(8) -0.0097(7) -0.0076(6) 0.0075(7) C14 0.0145(8) 0.0335(9) 0.0164(7) -0.0029(7) -0.0032(6) 0.0073(6) C13 0.0144(8) 0.0405(10) 0.0218(8) 0.0036(7) -0.0040(6) 0.0077(7) C12 0.0227(9) 0.0321(9) 0.0244(8) 0.0098(7) -0.0040(7) 0.0055(7) C11 0.0210(8) 0.0234(8) 0.0195(7) 0.0030(6) -0.0024(6) 0.0032(6) C20 0.0130(7) 0.0176(7) 0.0125(6) -0.0016(5) -0.0028(5) 0.0015(5) C22 0.0179(8) 0.0160(7) 0.0165(7) -0.0044(6) -0.0051(6) 0.0018(5) C21 0.0129(7) 0.0164(7) 0.0123(6) -0.0018(5) -0.0035(5) -0.0004(5) C23 0.0214(8) 0.0150(7) 0.0155(7) -0.0016(6) -0.0070(6) 0.0006(5) C24 0.0315(10) 0.0144(7) 0.0278(8) -0.0031(7) -0.0131(7) 0.0036(6) C25 0.0335(10) 0.0171(7) 0.0327(9) 0.0045(7) -0.0178(8) 0.0026(6) C34 0.0153(7) 0.0136(6) 0.0136(6) 0.0003(5) -0.0032(5) -0.0004(5) C33 0.0170(8) 0.0181(7) 0.0148(7) 0.0001(6) -0.0048(6) -0.0029(5) C32 0.0162(7) 0.0217(7) 0.0149(7) -0.0013(6) -0.0062(6) 0.0025(5) C31 0.0231(8) 0.0154(7) 0.0206(7) -0.0033(6) -0.0092(6) 0.0056(5) C30 0.0240(8) 0.0137(6) 0.0177(7) -0.0058(6) -0.0080(6) 0.0013(5) C29 0.0112(7) 0.0156(6) 0.0116(6) -0.0024(5) -0.0031(5) 0.0012(5) C28 0.0177(7) 0.0138(6) 0.0118(6) 0.0004(5) -0.0058(5) -0.0001(5) C27 0.0171(8) 0.0195(7) 0.0177(7) 0.0000(6) -0.0066(6) -0.0005(5) C26 0.0219(9) 0.0227(8) 0.0255(8) 0.0048(7) -0.0115(7) -0.0019(6) C37 0.0189(8) 0.0288(8) 0.0186(7) -0.0085(7) -0.0099(6) 0.0046(6) C36 0.0148(7) 0.0222(7) 0.0166(7) -0.0049(6) -0.0056(6) 0.0011(5) C35 0.0145(7) 0.0134(6) 0.0119(6) -0.0049(5) -0.0046(5) 0.0015(5) C38 0.0267(9) 0.0311(9) 0.0135(7) -0.0118(7) -0.0073(6) 0.0025(6) C39 0.0213(8) 0.0289(8) 0.0129(7) -0.0079(7) -0.0018(6) -0.0007(6) C40 0.0150(7) 0.0167(7) 0.0131(6) -0.0038(6) -0.0030(5) 0.0009(5) C41 0.0126(7) 0.0189(7) 0.0145(7) -0.0023(6) -0.0021(5) -0.0006(5) C42 0.0082(6) 0.0131(6) 0.0149(6) -0.0016(5) -0.0020(5) 0.0010(5) C43 0.0095(6) 0.0106(6) 0.0156(6) -0.0004(5) -0.0029(5) -0.0004(5) C44 0.0107(7) 0.0113(6) 0.0161(6) -0.0003(5) -0.0042(5) -0.0002(5) C45 0.0132(7) 0.0164(7) 0.0189(7) -0.0015(6) -0.0049(6) 0.0034(5) C46 0.0140(7) 0.0184(7) 0.0227(7) -0.0039(6) -0.0010(6) 0.0059(6) C54 0.0095(6) 0.0101(6) 0.0147(6) 0.0002(5) -0.0043(5) -0.0012(5) C53 0.0113(7) 0.0106(6) 0.0167(6) -0.0003(5) -0.0048(5) -0.0015(5) C52 0.0103(7) 0.0108(6) 0.0165(6) -0.0004(5) -0.0046(5) -0.0019(5) C51 0.0151(7) 0.0196(7) 0.0172(7) -0.0031(6) -0.0053(6) -0.0012(5) C50 0.0176(8) 0.0243(8) 0.0204(7) -0.0035(6) -0.0098(6) -0.0027(6) C49 0.0120(7) 0.0200(7) 0.0240(8) -0.0028(6) -0.0075(6) -0.0037(6) C48 0.0120(7) 0.0117(6) 0.0210(7) -0.0006(5) -0.0046(6) -0.0021(5) C47 0.0103(7) 0.0156(7) 0.0264(8) -0.0034(5) -0.0029(6) 0.0020(6) C55 0.0110(7) 0.0101(6) 0.0143(6) -0.0013(5) -0.0044(5) -0.0007(5) C56 0.0135(7) 0.0120(6) 0.0144(6) -0.0006(5) -0.0044(5) -0.0006(5) C57 0.0136(7) 0.0098(6) 0.0135(6) -0.0013(5) -0.0024(5) -0.0007(5) C58 0.0205(8) 0.0122(6) 0.0131(6) -0.0013(6) -0.0030(6) -0.0006(5) C59 0.0205(8) 0.0129(6) 0.0144(6) -0.0045(6) 0.0011(6) 0.0002(5) C68 0.0182(8) 0.0138(6) 0.0185(7) -0.0020(6) -0.0015(6) 0.0016(5) C67 0.0243(9) 0.0138(7) 0.0287(8) -0.0070(6) -0.0002(7) 0.0026(6) C66 0.0191(8) 0.0132(7) 0.0342(9) -0.0038(6) -0.0034(7) -0.0069(6) C65 0.0205(8) 0.0198(7) 0.0219(7) -0.0005(6) -0.0037(6) -0.0081(6) C64 0.0155(7) 0.0147(6) 0.0174(7) -0.0023(6) -0.0021(6) -0.0012(5) C63 0.0096(6) 0.0104(6) 0.0157(6) -0.0003(5) -0.0022(5) -0.0007(5) C62 0.0133(7) 0.0087(6) 0.0121(6) -0.0019(5) -0.0013(5) -0.0003(5) C61 0.0152(7) 0.0123(6) 0.0151(6) -0.0038(5) -0.0031(5) -0.0011(5) C60 0.0159(7) 0.0141(6) 0.0187(7) -0.0058(6) -0.0003(6) -0.0008(5) C69A 0.048(3) 0.048(3) 0.048(3) -0.0050(11) -0.0103(12) 0.0001(10) Cl1A 0.088(3) 0.228(7) 0.047(2) -0.061(4) -0.019(2) -0.017(3) Cl2A 0.131(4) 0.059(2) 0.053(2) 0.056(2) 0.054(2) 0.0241(14) Cl3A 0.055(2) 0.095(4) 0.089(4) -0.048(3) 0.012(2) -0.053(3) C69B 0.0198(11) 0.0213(11) 0.0178(11) -0.0029(8) -0.0005(7) -0.0016(8) Cl1B 0.0261(7) 0.0782(11) 0.0238(6) -0.0230(5) -0.0113(4) 0.0058(5) Cl2B 0.0265(8) 0.1025(18) 0.0388(8) 0.0126(8) -0.0028(6) 0.0264(9) Cl3B 0.0616(12) 0.0895(17) 0.102(3) -0.0030(11) -0.0066(13) -0.0606(19) _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 P1 O1 . 1.4739(13) ? P1 N1 . 1.6863(14) ? P1 N2 . 1.6874(15) ? P1 C29 . 1.7835(16) ? C1 C2 . 1.387(2) ? C1 N1 . 1.414(2) ? C1 C6 . 1.415(2) ? N1 C8 . 1.413(2) ? C2 C3 . 1.395(2) ? C2 H2 . 0.95 ? P2 O2 . 1.4685(13) ? P2 N3 . 1.6835(14) ? P2 N4 . 1.6896(13) ? P2 C63 . 1.7841(16) ? N2 C28 . 1.4101(19) ? N2 C21 . 1.416(2) ? N3 C42 . 1.4093(19) ? N3 C35 . 1.4126(19) ? C3 C4 . 1.403(3) ? C3 H3 . 0.95 ? N4 C62 . 1.4211(18) ? N4 C55 . 1.4227(19) ? C4 C5 . 1.370(3) ? C4 H4 . 0.95 ? C5 C6 . 1.409(2) ? C5 H5 . 0.95 ? C6 C7 . 1.424(3) ? C7 C8 . 1.374(2) ? C7 H7 . 0.95 ? C8 C9 . 1.451(2) ? C9 C20 . 1.391(2) ? C9 C10 . 1.481(2) ? C10 C11 . 1.382(2) ? C10 C19 . 1.407(2) ? C19 C14 . 1.400(2) ? C19 C18 . 1.413(2) ? C18 C17 . 1.382(2) ? C18 C20 . 1.480(2) ? C17 C16 . 1.425(2) ? C17 H17 . 0.95 ? C16 C15 . 1.383(3) ? C16 H16 . 0.95 ? C15 C14 . 1.425(3) ? C15 H15 . 0.95 ? C14 C13 . 1.425(3) ? C13 C12 . 1.377(3) ? C13 H13 . 0.95 ? C12 C11 . 1.422(3) ? C12 H12 . 0.95 ? C11 H11 . 0.95 ? C20 C21 . 1.453(2) ? C22 C21 . 1.372(2) ? C22 C23 . 1.428(2) ? C22 H22 . 0.95 ? C23 C24 . 1.407(2) ? C23 C28 . 1.411(2) ? C24 C25 . 1.377(3) ? C24 H24 . 0.95 ? C25 C26 . 1.401(3) ? C25 H25 . 0.95 ? C34 C33 . 1.392(2) ? C34 C29 . 1.396(2) ? C34 H34 . 0.95 ? C33 C32 . 1.392(2) ? C33 H33 . 0.95 ? C32 C31 . 1.388(2) ? C32 H32 . 0.95 ? C31 C30 . 1.390(2) ? C31 H31 . 0.95 ? C30 C29 . 1.396(2) ? C30 H30 . 0.95 ? C28 C27 . 1.392(2) ? C27 C26 . 1.390(2) ? C27 H27 . 0.95 ? C26 H26 . 0.95 ? C37 C36 . 1.392(2) ? C37 C38 . 1.406(3) ? C37 H37 . 0.95 ? C36 C35 . 1.391(2) ? C36 H36 . 0.95 ? C35 C40 . 1.415(2) ? C38 C39 . 1.383(2) ? C38 H38 . 0.95 ? C39 C40 . 1.403(2) ? C39 H39 . 0.95 ? C40 C41 . 1.434(2) ? C41 C42 . 1.372(2) ? C41 H41 . 0.95 ? C42 C43 . 1.453(2) ? C43 C54 . 1.396(2) ? C43 C44 . 1.476(2) ? C44 C45 . 1.380(2) ? C44 C53 . 1.409(2) ? C45 C46 . 1.421(2) ? C45 H45 . 0.95 ? C46 C47 . 1.380(2) ? C46 H46 . 0.95 ? C54 C55 . 1.446(2) ? C54 C52 . 1.482(2) ? C53 C48 . 1.395(2) ? C53 C52 . 1.414(2) ? C52 C51 . 1.384(2) ? C51 C50 . 1.420(2) ? C51 H51 . 0.95 ? C50 C49 . 1.377(2) ? C50 H50 . 0.95 ? C49 C48 . 1.419(2) ? C49 H49 . 0.95 ? C48 C47 . 1.420(2) ? C47 H47 . 0.95 ? C55 C56 . 1.375(2) ? C56 C57 . 1.429(2) ? C56 H56 . 0.95 ? C57 C58 . 1.409(2) ? C57 C62 . 1.412(2) ? C58 C59 . 1.381(2) ? C58 H58 . 0.95 ? C59 C60 . 1.407(2) ? C59 H59 . 0.95 ? C68 C67 . 1.391(2) ? C68 C63 . 1.399(2) ? C68 H68 . 0.95 ? C67 C66 . 1.387(3) ? C67 H67 . 0.95 ? C66 C65 . 1.391(2) ? C66 H66 . 0.95 ? C65 C64 . 1.390(2) ? C65 H65 . 0.95 ? C64 C63 . 1.400(2) ? C64 H64 . 0.95 ? C62 C61 . 1.391(2) ? C61 C60 . 1.391(2) ? C61 H61 . 0.95 ? C60 H60 . 0.95 ? C69A Cl3A . 1.604(15) ? C69A Cl1A . 1.726(16) ? C69A Cl2A . 1.891(14) ? C69A H69A . 1.0 ? C69B Cl2B . 1.697(6) ? C69B Cl1B . 1.733(5) ? C69B Cl3B . 1.784(6) ? C69B H69B . 1.0 ? 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 P1 N1 . . 112.83(7) ? O1 P1 N2 . . 112.51(7) ? N1 P1 N2 . . 103.57(7) ? O1 P1 C29 . . 117.37(7) ? N1 P1 C29 . . 104.16(7) ? N2 P1 C29 . . 105.09(7) ? C2 C1 N1 . . 130.18(15) ? C2 C1 C6 . . 122.68(15) ? N1 C1 C6 . . 107.13(15) ? C8 N1 C1 . . 107.89(13) ? C8 N1 P1 . . 124.38(10) ? C1 N1 P1 . . 127.27(12) ? C1 C2 C3 . . 116.55(17) ? C1 C2 H2 . . 121.7 ? C3 C2 H2 . . 121.7 ? O2 P2 N3 . . 111.21(6) ? O2 P2 N4 . . 112.61(6) ? N3 P2 N4 . . 103.48(7) ? O2 P2 C63 . . 116.92(7) ? N3 P2 C63 . . 106.54(7) ? N4 P2 C63 . . 104.99(7) ? C28 N2 C21 . . 107.79(12) ? C28 N2 P1 . . 127.39(11) ? C21 N2 P1 . . 124.69(10) ? C42 N3 C35 . . 108.14(12) ? C42 N3 P2 . . 124.57(10) ? C35 N3 P2 . . 127.28(11) ? C2 C3 C4 . . 121.88(19) ? C2 C3 H3 . . 119.1 ? C4 C3 H3 . . 119.1 ? C62 N4 C55 . . 107.66(12) ? C62 N4 P2 . . 121.94(10) ? C55 N4 P2 . . 122.51(9) ? C5 C4 C3 . . 120.97(16) ? C5 C4 H4 . . 119.5 ? C3 C4 H4 . . 119.5 ? C4 C5 C6 . . 119.04(18) ? C4 C5 H5 . . 120.5 ? C6 C5 H5 . . 120.5 ? C5 C6 C1 . . 118.87(17) ? C5 C6 C7 . . 133.21(17) ? C1 C6 C7 . . 107.91(14) ? C8 C7 C6 . . 108.08(15) ? C8 C7 H7 . . 126.0 ? C6 C7 H7 . . 126.0 ? C7 C8 N1 . . 108.99(14) ? C7 C8 C9 . . 128.03(16) ? N1 C8 C9 . . 122.96(13) ? C20 C9 C8 . . 129.21(14) ? C20 C9 C10 . . 108.04(14) ? C8 C9 C10 . . 122.70(14) ? C11 C10 C19 . . 118.42(16) ? C11 C10 C9 . . 135.02(16) ? C19 C10 C9 . . 106.55(14) ? C14 C19 C10 . . 124.66(15) ? C14 C19 C18 . . 124.61(15) ? C10 C19 C18 . . 110.73(15) ? C17 C18 C19 . . 118.21(15) ? C17 C18 C20 . . 135.70(15) ? C19 C18 C20 . . 106.10(14) ? C18 C17 C16 . . 118.42(15) ? C18 C17 H17 . . 120.8 ? C16 C17 H17 . . 120.8 ? C15 C16 C17 . . 122.87(16) ? C15 C16 H16 . . 118.6 ? C17 C16 H16 . . 118.6 ? C16 C15 C14 . . 119.70(16) ? C16 C15 H15 . . 120.1 ? C14 C15 H15 . . 120.1 ? C19 C14 C13 . . 115.97(16) ? C19 C14 C15 . . 116.17(16) ? C13 C14 C15 . . 127.86(17) ? C12 C13 C14 . . 119.63(17) ? C12 C13 H13 . . 120.2 ? C14 C13 H13 . . 120.2 ? C13 C12 C11 . . 123.26(16) ? C13 C12 H12 . . 118.4 ? C11 C12 H12 . . 118.4 ? C10 C11 C12 . . 117.99(17) ? C10 C11 H11 . . 121.0 ? C12 C11 H11 . . 121.0 ? C9 C20 C21 . . 128.93(14) ? C9 C20 C18 . . 108.55(13) ? C21 C20 C18 . . 122.47(14) ? C21 C22 C23 . . 107.97(14) ? C21 C22 H22 . . 126.0 ? C23 C22 H22 . . 126.0 ? C22 C21 N2 . . 109.01(13) ? C22 C21 C20 . . 128.14(15) ? N2 C21 C20 . . 122.83(13) ? C24 C23 C28 . . 119.16(16) ? C24 C23 C22 . . 133.04(16) ? C28 C23 C22 . . 107.80(14) ? C25 C24 C23 . . 118.89(16) ? C25 C24 H24 . . 120.6 ? C23 C24 H24 . . 120.6 ? C24 C25 C26 . . 120.86(15) ? C24 C25 H25 . . 119.6 ? C26 C25 H25 . . 119.6 ? C33 C34 C29 . . 119.60(14) ? C33 C34 H34 . . 120.2 ? C29 C34 H34 . . 120.2 ? C34 C33 C32 . . 120.30(14) ? C34 C33 H33 . . 119.9 ? C32 C33 H33 . . 119.9 ? C31 C32 C33 . . 120.11(14) ? C31 C32 H32 . . 119.9 ? C33 C32 H32 . . 119.9 ? C32 C31 C30 . . 119.91(14) ? C32 C31 H31 . . 120.0 ? C30 C31 H31 . . 120.0 ? C31 C30 C29 . . 120.14(14) ? C31 C30 H30 . . 119.9 ? C29 C30 H30 . . 119.9 ? C34 C29 C30 . . 119.90(14) ? C34 C29 P1 . . 120.85(11) ? C30 C29 P1 . . 119.25(11) ? C27 C28 N2 . . 130.27(14) ? C27 C28 C23 . . 122.31(14) ? N2 C28 C23 . . 107.42(14) ? C26 C27 C28 . . 116.89(15) ? C26 C27 H27 . . 121.6 ? C28 C27 H27 . . 121.6 ? C27 C26 C25 . . 121.88(17) ? C27 C26 H26 . . 119.1 ? C25 C26 H26 . . 119.1 ? C36 C37 C38 . . 121.24(16) ? C36 C37 H37 . . 119.4 ? C38 C37 H37 . . 119.4 ? C35 C36 C37 . . 117.37(15) ? C35 C36 H36 . . 121.3 ? C37 C36 H36 . . 121.3 ? C36 C35 N3 . . 130.35(13) ? C36 C35 C40 . . 122.30(14) ? N3 C35 C40 . . 107.35(13) ? C39 C38 C37 . . 120.98(15) ? C39 C38 H38 . . 119.5 ? C37 C38 H38 . . 119.5 ? C38 C39 C40 . . 119.00(15) ? C38 C39 H39 . . 120.5 ? C40 C39 H39 . . 120.5 ? C39 C40 C35 . . 119.09(15) ? C39 C40 C41 . . 133.56(15) ? C35 C40 C41 . . 107.34(13) ? C42 C41 C40 . . 108.23(14) ? C42 C41 H41 . . 125.9 ? C40 C41 H41 . . 125.9 ? C41 C42 N3 . . 108.94(13) ? C41 C42 C43 . . 127.58(14) ? N3 C42 C43 . . 123.41(13) ? C54 C43 C42 . . 131.23(14) ? C54 C43 C44 . . 108.73(12) ? C42 C43 C44 . . 120.00(13) ? C45 C44 C53 . . 118.36(14) ? C45 C44 C43 . . 135.36(14) ? C53 C44 C43 . . 106.21(13) ? C44 C45 C46 . . 118.80(14) ? C44 C45 H45 . . 120.6 ? C46 C45 H45 . . 120.6 ? C47 C46 C45 . . 122.06(14) ? C47 C46 H46 . . 119.0 ? C45 C46 H46 . . 119.0 ? C43 C54 C55 . . 128.96(13) ? C43 C54 C52 . . 107.80(13) ? C55 C54 C52 . . 123.23(13) ? C48 C53 C44 . . 124.15(14) ? C48 C53 C52 . . 124.96(14) ? C44 C53 C52 . . 110.85(13) ? C51 C52 C53 . . 117.18(14) ? C51 C52 C54 . . 136.47(14) ? C53 C52 C54 . . 106.36(13) ? C52 C51 C50 . . 119.10(14) ? C52 C51 H51 . . 120.5 ? C50 C51 H51 . . 120.5 ? C49 C50 C51 . . 122.69(15) ? C49 C50 H50 . . 118.7 ? C51 C50 H50 . . 118.7 ? C50 C49 C48 . . 119.65(15) ? C50 C49 H49 . . 120.2 ? C48 C49 H49 . . 120.2 ? C53 C48 C49 . . 116.36(14) ? C53 C48 C47 . . 116.40(14) ? C49 C48 C47 . . 127.23(15) ? C46 C47 C48 . . 120.18(15) ? C46 C47 H47 . . 119.9 ? C48 C47 H47 . . 119.9 ? C56 C55 N4 . . 108.50(13) ? C56 C55 C54 . . 129.15(14) ? N4 C55 C54 . . 122.34(13) ? C55 C56 C57 . . 108.73(13) ? C55 C56 H56 . . 125.6 ? C57 C56 H56 . . 125.6 ? C58 C57 C62 . . 119.10(14) ? C58 C57 C56 . . 133.39(14) ? C62 C57 C56 . . 107.50(13) ? C59 C58 C57 . . 118.70(14) ? C59 C58 H58 . . 120.7 ? C57 C58 H58 . . 120.7 ? C58 C59 C60 . . 121.11(14) ? C58 C59 H59 . . 119.4 ? C60 C59 H59 . . 119.4 ? C67 C68 C63 . . 119.62(15) ? C67 C68 H68 . . 120.2 ? C63 C68 H68 . . 120.2 ? C66 C67 C68 . . 120.29(15) ? C66 C67 H67 . . 119.9 ? C68 C67 H67 . . 119.9 ? C67 C66 C65 . . 120.31(15) ? C67 C66 H66 . . 119.8 ? C65 C66 H66 . . 119.8 ? C64 C65 C66 . . 119.94(15) ? C64 C65 H65 . . 120.0 ? C66 C65 H65 . . 120.0 ? C65 C64 C63 . . 119.91(14) ? C65 C64 H64 . . 120.0 ? C63 C64 H64 . . 120.0 ? C68 C63 C64 . . 119.92(14) ? C68 C63 P2 . . 121.42(12) ? C64 C63 P2 . . 118.64(11) ? C61 C62 C57 . . 122.49(13) ? C61 C62 N4 . . 129.86(13) ? C57 C62 N4 . . 107.57(13) ? C62 C61 C60 . . 117.12(14) ? C62 C61 H61 . . 121.4 ? C60 C61 H61 . . 121.4 ? C61 C60 C59 . . 121.39(15) ? C61 C60 H60 . . 119.3 ? C59 C60 H60 . . 119.3 ? Cl3A C69A Cl1A . . 113.1(9) ? Cl3A C69A Cl2A . . 110.5(9) ? Cl1A C69A Cl2A . . 103.3(7) ? Cl3A C69A H69A . . 109.9 ? Cl1A C69A H69A . . 109.9 ? Cl2A C69A H69A . . 109.9 ? Cl2B C69B Cl1B . . 116.0(3) ? Cl2B C69B Cl3B . . 110.3(3) ? Cl1B C69B Cl3B . . 108.7(3) ? Cl2B C69B H69B . . 107.1 ? Cl1B C69B H69B . . 107.1 ? Cl3B C69B H69B . . 107.1 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 C1 N1 C8 . . . . -178.94(15) ? C6 C1 N1 C8 . . . . 0.16(16) ? C2 C1 N1 P1 . . . . 8.6(2) ? C6 C1 N1 P1 . . . . -172.29(11) ? O1 P1 N1 C8 . . . . -175.70(11) ? N2 P1 N1 C8 . . . . 62.37(13) ? C29 P1 N1 C8 . . . . -47.34(13) ? O1 P1 N1 C1 . . . . -4.41(15) ? N2 P1 N1 C1 . . . . -126.34(13) ? C29 P1 N1 C1 . . . . 123.96(13) ? N1 C1 C2 C3 . . . . 178.55(15) ? C6 C1 C2 C3 . . . . -0.4(2) ? O1 P1 N2 C28 . . . . 2.10(14) ? N1 P1 N2 C28 . . . . 124.24(13) ? C29 P1 N2 C28 . . . . -126.75(12) ? O1 P1 N2 C21 . . . . 177.48(11) ? N1 P1 N2 C21 . . . . -60.37(13) ? C29 P1 N2 C21 . . . . 48.64(13) ? O2 P2 N3 C42 . . . . 173.99(11) ? N4 P2 N3 C42 . . . . 52.85(13) ? C63 P2 N3 C42 . . . . -57.56(13) ? O2 P2 N3 C35 . . . . -6.91(14) ? N4 P2 N3 C35 . . . . -128.05(12) ? C63 P2 N3 C35 . . . . 121.54(12) ? C1 C2 C3 C4 . . . . 0.2(2) ? O2 P2 N4 C62 . . . . 20.38(13) ? N3 P2 N4 C62 . . . . 140.57(11) ? C63 P2 N4 C62 . . . . -107.88(11) ? O2 P2 N4 C55 . . . . 165.61(10) ? N3 P2 N4 C55 . . . . -74.20(12) ? C63 P2 N4 C55 . . . . 37.34(12) ? C2 C3 C4 C5 . . . . 0.0(3) ? C3 C4 C5 C6 . . . . 0.1(2) ? C4 C5 C6 C1 . . . . -0.4(2) ? C4 C5 C6 C7 . . . . -179.03(17) ? C2 C1 C6 C5 . . . . 0.5(2) ? N1 C1 C6 C5 . . . . -178.64(13) ? C2 C1 C6 C7 . . . . 179.52(14) ? N1 C1 C6 C7 . . . . 0.33(17) ? C5 C6 C7 C8 . . . . 178.05(17) ? C1 C6 C7 C8 . . . . -0.72(18) ? C6 C7 C8 N1 . . . . 0.83(17) ? C6 C7 C8 C9 . . . . -177.49(14) ? C1 N1 C8 C7 . . . . -0.62(16) ? P1 N1 C8 C7 . . . . 172.11(11) ? C1 N1 C8 C9 . . . . 177.80(13) ? P1 N1 C8 C9 . . . . -9.5(2) ? C7 C8 C9 C20 . . . . 145.58(17) ? N1 C8 C9 C20 . . . . -32.5(2) ? C7 C8 C9 C10 . . . . -31.7(2) ? N1 C8 C9 C10 . . . . 150.22(14) ? C20 C9 C10 C11 . . . . 178.01(17) ? C8 C9 C10 C11 . . . . -4.2(3) ? C20 C9 C10 C19 . . . . -0.77(16) ? C8 C9 C10 C19 . . . . 176.99(13) ? C11 C10 C19 C14 . . . . 2.4(2) ? C9 C10 C19 C14 . . . . -178.57(14) ? C11 C10 C19 C18 . . . . -177.53(14) ? C9 C10 C19 C18 . . . . 1.49(17) ? C14 C19 C18 C17 . . . . -1.4(2) ? C10 C19 C18 C17 . . . . 178.50(13) ? C14 C19 C18 C20 . . . . 178.46(14) ? C10 C19 C18 C20 . . . . -1.60(17) ? C19 C18 C17 C16 . . . . 2.0(2) ? C20 C18 C17 C16 . . . . -177.87(16) ? C18 C17 C16 C15 . . . . -1.3(2) ? C17 C16 C15 C14 . . . . -0.2(2) ? C10 C19 C14 C13 . . . . 0.0(2) ? C18 C19 C14 C13 . . . . 179.95(15) ? C10 C19 C14 C15 . . . . -179.94(15) ? C18 C19 C14 C15 . . . . 0.0(2) ? C16 C15 C14 C19 . . . . 0.8(2) ? C16 C15 C14 C13 . . . . -179.13(16) ? C19 C14 C13 C12 . . . . -1.7(2) ? C15 C14 C13 C12 . . . . 178.23(17) ? C14 C13 C12 C11 . . . . 1.1(3) ? C19 C10 C11 C12 . . . . -3.0(2) ? C9 C10 C11 C12 . . . . 178.33(16) ? C13 C12 C11 C10 . . . . 1.4(3) ? C8 C9 C20 C21 . . . . -0.2(3) ? C10 C9 C20 C21 . . . . 177.38(14) ? C8 C9 C20 C18 . . . . -177.76(14) ? C10 C9 C20 C18 . . . . -0.19(16) ? C17 C18 C20 C9 . . . . -179.04(17) ? C19 C18 C20 C9 . . . . 1.08(16) ? C17 C18 C20 C21 . . . . 3.2(3) ? C19 C18 C20 C21 . . . . -176.69(13) ? C23 C22 C21 N2 . . . . -0.62(17) ? C23 C22 C21 C20 . . . . 177.86(14) ? C28 N2 C21 C22 . . . . 0.77(16) ? P1 N2 C21 C22 . . . . -175.38(11) ? C28 N2 C21 C20 . . . . -177.81(13) ? P1 N2 C21 C20 . . . . 6.0(2) ? C9 C20 C21 C22 . . . . -143.91(17) ? C18 C20 C21 C22 . . . . 33.4(2) ? C9 C20 C21 N2 . . . . 34.4(2) ? C18 C20 C21 N2 . . . . -148.34(14) ? C21 C22 C23 C24 . . . . 179.93(17) ? C21 C22 C23 C28 . . . . 0.25(17) ? C28 C23 C24 C25 . . . . 0.3(2) ? C22 C23 C24 C25 . . . . -179.33(17) ? C23 C24 C25 C26 . . . . -0.7(3) ? C29 C34 C33 C32 . . . . -1.0(2) ? C34 C33 C32 C31 . . . . -0.7(2) ? C33 C32 C31 C30 . . . . 1.8(2) ? C32 C31 C30 C29 . . . . -1.2(3) ? C33 C34 C29 C30 . . . . 1.7(2) ? C33 C34 C29 P1 . . . . -178.01(12) ? C31 C30 C29 C34 . . . . -0.6(2) ? C31 C30 C29 P1 . . . . 179.11(13) ? O1 P1 C29 C34 . . . . -93.71(13) ? N1 P1 C29 C34 . . . . 140.76(13) ? N2 P1 C29 C34 . . . . 32.17(14) ? O1 P1 C29 C30 . . . . 86.60(14) ? N1 P1 C29 C30 . . . . -38.93(14) ? N2 P1 C29 C30 . . . . -147.52(13) ? C21 N2 C28 C27 . . . . 179.74(15) ? P1 N2 C28 C27 . . . . -4.2(2) ? C21 N2 C28 C23 . . . . -0.60(15) ? P1 N2 C28 C23 . . . . 175.41(11) ? C24 C23 C28 C27 . . . . 0.2(2) ? C22 C23 C28 C27 . . . . 179.92(14) ? C24 C23 C28 N2 . . . . -179.51(14) ? C22 C23 C28 N2 . . . . 0.23(16) ? N2 C28 C27 C26 . . . . 179.26(15) ? C23 C28 C27 C26 . . . . -0.4(2) ? C28 C27 C26 C25 . . . . 0.0(2) ? C24 C25 C26 C27 . . . . 0.5(3) ? C38 C37 C36 C35 . . . . -1.5(2) ? C37 C36 C35 N3 . . . . -177.65(15) ? C37 C36 C35 C40 . . . . 1.3(2) ? C42 N3 C35 C36 . . . . 178.57(15) ? P2 N3 C35 C36 . . . . -0.7(2) ? C42 N3 C35 C40 . . . . -0.50(15) ? P2 N3 C35 C40 . . . . -179.72(10) ? C36 C37 C38 C39 . . . . 0.4(3) ? C37 C38 C39 C40 . . . . 1.0(2) ? C38 C39 C40 C35 . . . . -1.2(2) ? C38 C39 C40 C41 . . . . 177.63(16) ? C36 C35 C40 C39 . . . . 0.0(2) ? N3 C35 C40 C39 . . . . 179.18(13) ? C36 C35 C40 C41 . . . . -179.08(14) ? N3 C35 C40 C41 . . . . 0.08(16) ? C39 C40 C41 C42 . . . . -178.53(17) ? C35 C40 C41 C42 . . . . 0.38(17) ? C40 C41 C42 N3 . . . . -0.70(16) ? C40 C41 C42 C43 . . . . 176.39(14) ? C35 N3 C42 C41 . . . . 0.75(16) ? P2 N3 C42 C41 . . . . 180.00(10) ? C35 N3 C42 C43 . . . . -176.48(13) ? P2 N3 C42 C43 . . . . 2.77(19) ? C41 C42 C43 C54 . . . . 146.94(16) ? N3 C42 C43 C54 . . . . -36.4(2) ? C41 C42 C43 C44 . . . . -30.4(2) ? N3 C42 C43 C44 . . . . 146.32(14) ? C54 C43 C44 C45 . . . . 173.95(16) ? C42 C43 C44 C45 . . . . -8.2(2) ? C54 C43 C44 C53 . . . . -2.56(16) ? C42 C43 C44 C53 . . . . 175.31(12) ? C53 C44 C45 C46 . . . . -1.5(2) ? C43 C44 C45 C46 . . . . -177.72(15) ? C44 C45 C46 C47 . . . . -0.5(2) ? C42 C43 C54 C55 . . . . 3.7(3) ? C44 C43 C54 C55 . . . . -178.72(13) ? C42 C43 C54 C52 . . . . -175.57(14) ? C44 C43 C54 C52 . . . . 1.98(15) ? C45 C44 C53 C48 . . . . 2.7(2) ? C43 C44 C53 C48 . . . . 179.93(13) ? C45 C44 C53 C52 . . . . -175.06(13) ? C43 C44 C53 C52 . . . . 2.15(16) ? C48 C53 C52 C51 . . . . 0.7(2) ? C44 C53 C52 C51 . . . . 178.50(13) ? C48 C53 C52 C54 . . . . -178.73(13) ? C44 C53 C52 C54 . . . . -0.98(16) ? C43 C54 C52 C51 . . . . -179.99(16) ? C55 C54 C52 C51 . . . . 0.7(3) ? C43 C54 C52 C53 . . . . -0.67(15) ? C55 C54 C52 C53 . . . . 179.98(13) ? C53 C52 C51 C50 . . . . 1.4(2) ? C54 C52 C51 C50 . . . . -179.34(16) ? C52 C51 C50 C49 . . . . -1.5(2) ? C51 C50 C49 C48 . . . . -0.5(2) ? C44 C53 C48 C49 . . . . 179.83(14) ? C52 C53 C48 C49 . . . . -2.7(2) ? C44 C53 C48 C47 . . . . -1.7(2) ? C52 C53 C48 C47 . . . . 175.81(13) ? C50 C49 C48 C53 . . . . 2.5(2) ? C50 C49 C48 C47 . . . . -175.82(15) ? C45 C46 C47 C48 . . . . 1.6(2) ? C53 C48 C47 C46 . . . . -0.5(2) ? C49 C48 C47 C46 . . . . 177.80(15) ? C62 N4 C55 C56 . . . . 1.18(15) ? P2 N4 C55 C56 . . . . -148.30(10) ? C62 N4 C55 C54 . . . . -177.81(12) ? P2 N4 C55 C54 . . . . 32.72(18) ? C43 C54 C55 C56 . . . . -164.48(15) ? C52 C54 C55 C56 . . . . 14.7(2) ? C43 C54 C55 N4 . . . . 14.3(2) ? C52 C54 C55 N4 . . . . -166.51(12) ? N4 C55 C56 C57 . . . . -0.11(15) ? C54 C55 C56 C57 . . . . 178.78(14) ? C55 C56 C57 C58 . . . . -179.99(15) ? C55 C56 C57 C62 . . . . -1.01(16) ? C62 C57 C58 C59 . . . . -2.0(2) ? C56 C57 C58 C59 . . . . 176.86(15) ? C57 C58 C59 C60 . . . . -0.5(2) ? C63 C68 C67 C66 . . . . 0.4(3) ? C68 C67 C66 C65 . . . . 0.7(3) ? C67 C66 C65 C64 . . . . -1.0(3) ? C66 C65 C64 C63 . . . . 0.1(2) ? C67 C68 C63 C64 . . . . -1.3(2) ? C67 C68 C63 P2 . . . . -179.49(13) ? C65 C64 C63 C68 . . . . 1.0(2) ? C65 C64 C63 P2 . . . . 179.31(12) ? O2 P2 C63 C68 . . . . 95.10(13) ? N3 P2 C63 C68 . . . . -29.94(14) ? N4 P2 C63 C68 . . . . -139.29(13) ? O2 P2 C63 C64 . . . . -83.16(13) ? N3 P2 C63 C64 . . . . 151.80(12) ? N4 P2 C63 C64 . . . . 42.45(14) ? C58 C57 C62 C61 . . . . 3.8(2) ? C56 C57 C62 C61 . . . . -175.36(13) ? C58 C57 C62 N4 . . . . -179.13(12) ? C56 C57 C62 N4 . . . . 1.72(15) ? C55 N4 C62 C61 . . . . 175.00(14) ? P2 N4 C62 C61 . . . . -35.3(2) ? C55 N4 C62 C57 . . . . -1.79(14) ? P2 N4 C62 C57 . . . . 147.90(10) ? C57 C62 C61 C60 . . . . -2.8(2) ? N4 C62 C61 C60 . . . . -179.19(14) ? C62 C61 C60 C59 . . . . 0.2(2) ? C58 C59 C60 C61 . . . . 1.5(2) ? ####################################################################### # # 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_I _database_code_depnum_ccdc_archive 'CCDC 1427666' _audit_update_record ; 2015-09-25 deposited with the CCDC. 2016-03-15 downloaded from the CCDC. ; # start Validation Reply Form _vrf_PLAT094_I ; PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.84 Report RESPONSE: The largest peaks in the difference (electron density) map are along the covalent bonds between atoms ; # Added during the CSD deposition process: Friday 25th of September 2015 01:59:27 PM # end Validation Reply Form _chemical_name_systematic ? _chemical_name_common YR4 _chemical_formula_moiety ? _chemical_formula_sum 'C28 H17 N4 P S' _chemical_formula_iupac ? _chemical_formula_weight 472.48 _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P c c n' _space_group_name_Hall '-P 2ab 2ac' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x+1/2, -y+1/2, z' '-x, -y, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' 'x-1/2, y-1/2, -z' _cell_length_a 17.008(8) _cell_length_b 32.243(12) _cell_length_c 7.688(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4216.(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9166 _cell_measurement_theta_min 2.7036 _cell_measurement_theta_max 33.1012 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'rectangular rod' _exptl_crystal_colour 'translucent intense yellow' _exptl_crystal_size_max 0.358 _exptl_crystal_size_mid 0.171 _exptl_crystal_size_min 0.148 _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/5 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.96 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'BRUKER APEX II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.4167 _diffrn_reflns_number 98307 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_unetI/netI 0.0150 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 32.09 _diffrn_reflns_theta_full 32.09 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _refine_special_details ; ; _reflns_number_total 7382 _reflns_number_gt 6489 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_gt 0.0975 _refine_ls_wR_factor_ref 0.1021 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_number_reflns 7382 _refine_ls_number_parameters 307 _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^)+(0.0565P)^2^+2.1210P] 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 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.694 _refine_diff_density_min -0.244 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' P P 0.1023 0.0942 '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 v4.2.4' _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? 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 S S1 0.63952(2) 0.06657(2) 0.73864(3) 0.01770(7) Uani d . . . 1 . . N N1 0.52104(5) 0.15615(3) -0.08677(11) 0.01146(15) Uani d . . . 1 . . C C1 0.55719(6) 0.17934(3) -0.21785(13) 0.01127(17) Uani d . . . 1 . . P P1 0.42275(2) 0.14674(2) -0.09060(3) 0.01027(6) Uani d . . . 1 . . C C2 0.52388(6) 0.19766(3) -0.36451(14) 0.01428(19) Uani d . . . 1 . . H H2 0.4693 0.1954 -0.3885 0.017 Uiso calc U . R 1 . . N N2 0.42225(5) 0.09450(3) -0.06687(12) 0.01140(15) Uani d . . . 1 . . N N3 0.67138(6) 0.09971(3) 0.59836(12) 0.01696(18) Uani d . . . 1 . . C C3 0.57395(7) 0.21934(3) -0.47393(14) 0.01590(19) Uani d . . . 1 . . H H3 0.5533 0.2323 -0.5752 0.019 Uiso calc U . R 1 . . N N4 0.56045(6) 0.04988(3) 0.64584(12) 0.01659(18) Uani d . . . 1 . . C C4 0.65468(7) 0.22250(3) -0.43755(14) 0.01598(19) Uani d . . . 1 . . H H4 0.6874 0.2381 -0.5134 0.019 Uiso calc U . R 1 . . C C6 0.63816(6) 0.18119(3) -0.18171(13) 0.01128(17) Uani d . . . 1 . . C C5 0.68737(6) 0.20352(3) -0.29419(14) 0.01394(18) Uani d . . . 1 . . H H5 0.7422 0.2055 -0.272 0.017 Uiso calc U . R 1 . . C C9 0.56635(6) 0.11717(3) 0.18439(13) 0.01094(17) Uani d . . . 1 . . C C8 0.57994(6) 0.14242(3) 0.02784(13) 0.01067(17) Uani d . . . 1 . . C C7 0.65111(6) 0.15735(3) -0.02813(13) 0.01211(17) Uani d . . . 1 . . H H7 0.7005 0.1526 0.0261 0.015 Uiso calc U . R 1 . . C C10 0.62119(6) 0.12310(3) 0.31462(13) 0.01335(18) Uani d . . . 1 . . H H10 0.6608 0.1436 0.3013 0.016 Uiso calc U . R 1 . . C C11 0.61875(6) 0.09889(3) 0.46680(13) 0.01327(18) Uani d . . . 1 . . C C12 0.55602(6) 0.07031(3) 0.49318(13) 0.01303(18) Uani d . . . 1 . . C C16 0.42974(6) 0.03016(3) 0.04667(14) 0.01266(18) Uani d . . . 1 . . H H16 0.4419 0.0076 0.1217 0.015 Uiso calc U . R 1 . . C C15 0.45353(6) 0.07041(3) 0.06842(13) 0.01130(17) Uani d . . . 1 . . C C14 0.50529(6) 0.08587(3) 0.20681(13) 0.01129(17) Uani d . . . 1 . . C C13 0.49921(6) 0.06452(3) 0.36226(13) 0.01335(18) Uani d . . . 1 . . H H13 0.4567 0.0459 0.3807 0.016 Uiso calc U . R 1 . . C C17 0.38338(6) 0.02780(3) -0.10819(14) 0.01223(17) Uani d . . . 1 . . C C20 0.30505(6) 0.04489(4) -0.41773(15) 0.0167(2) Uani d . . . 1 . . H H20 0.2782 0.0501 -0.5238 0.02 Uiso calc U . R 1 . . C C19 0.30706(6) 0.00435(3) -0.35077(15) 0.0167(2) Uani d . . . 1 . . H H19 0.2812 -0.0173 -0.4119 0.02 Uiso calc U . R 1 . . C C18 0.34607(6) -0.00459(3) -0.19731(15) 0.01504(19) Uani d . . . 1 . . H H18 0.3475 -0.0321 -0.1533 0.018 Uiso calc U . R 1 . . C C21 0.34149(6) 0.07735(3) -0.33207(14) 0.01431(18) Uani d . . . 1 . . H H21 0.3403 0.1048 -0.3773 0.017 Uiso calc U . R 1 . . C C22 0.37991(6) 0.06821(3) -0.17699(13) 0.01165(17) Uani d . . . 1 . . C C23 0.39068(6) 0.16409(3) 0.12269(13) 0.01176(17) Uani d . . . 1 . . C C24 0.33410(6) 0.14188(3) 0.21517(14) 0.01510(19) Uani d . . . 1 . . H H24 0.3208 0.1145 0.1803 0.018 Uiso calc U . R 1 . . C C26 0.31585(8) 0.19964(4) 0.40947(16) 0.0252(3) Uani d . . . 1 . . H H26 0.29 0.2117 0.5066 0.03 Uiso calc U . R 1 . . C C27 0.37236(8) 0.22190(4) 0.31875(17) 0.0243(2) Uani d . . . 1 . . H H27 0.3853 0.2493 0.3539 0.029 Uiso calc U . R 1 . . C C28 0.41001(7) 0.20421(3) 0.17674(15) 0.0173(2) Uani d . . . 1 . . H H28 0.4491 0.2195 0.116 0.021 Uiso calc U . R 1 . . C C25 0.29727(7) 0.15950(4) 0.35721(15) 0.0204(2) Uani d . . . 1 . . H H25 0.259 0.1441 0.4197 0.024 Uiso calc U . R 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 S1 0.02465(14) 0.01805(13) 0.01040(12) -0.00027(10) -0.00452(9) 0.00265(9) N1 0.0105(4) 0.0132(4) 0.0107(4) -0.0004(3) 0.0002(3) 0.0042(3) C1 0.0124(4) 0.0106(4) 0.0109(4) 0.0004(3) 0.0014(3) 0.0013(3) P1 0.00966(11) 0.01049(11) 0.01065(12) -0.00001(8) -0.00050(8) 0.00223(8) C2 0.0142(4) 0.0155(4) 0.0131(4) 0.0003(3) 0.0002(3) 0.0042(3) N2 0.0125(4) 0.0100(3) 0.0117(4) -0.0003(3) -0.0023(3) 0.0016(3) N3 0.0229(5) 0.0159(4) 0.0122(4) -0.0011(3) -0.0046(3) 0.0014(3) C3 0.0182(5) 0.0164(5) 0.0130(4) 0.0001(4) 0.0012(4) 0.0043(4) N4 0.0201(4) 0.0191(4) 0.0106(4) 0.0008(3) -0.0005(3) 0.0038(3) C4 0.0175(5) 0.0159(5) 0.0145(4) -0.0024(4) 0.0041(4) 0.0024(4) C6 0.0122(4) 0.0111(4) 0.0106(4) -0.0006(3) 0.0015(3) -0.0005(3) C5 0.0133(4) 0.0148(4) 0.0137(4) -0.0017(3) 0.0029(3) 0.0002(3) C9 0.0124(4) 0.0107(4) 0.0097(4) 0.0005(3) -0.0003(3) 0.0012(3) C8 0.0113(4) 0.0109(4) 0.0098(4) 0.0000(3) -0.0008(3) 0.0009(3) C7 0.0120(4) 0.0132(4) 0.0112(4) -0.0006(3) -0.0007(3) 0.0005(3) C10 0.0162(4) 0.0126(4) 0.0113(4) -0.0014(3) -0.0020(3) 0.0015(3) C11 0.0169(4) 0.0124(4) 0.0105(4) 0.0007(3) -0.0013(3) -0.0002(3) C12 0.0155(4) 0.0134(4) 0.0101(4) 0.0019(3) 0.0002(3) 0.0020(3) C16 0.0129(4) 0.0116(4) 0.0135(4) -0.0001(3) 0.0003(3) 0.0020(3) C15 0.0110(4) 0.0119(4) 0.0110(4) 0.0003(3) -0.0001(3) 0.0021(3) C14 0.0109(4) 0.0119(4) 0.0111(4) 0.0005(3) -0.0001(3) 0.0017(3) C13 0.0133(4) 0.0146(4) 0.0121(4) -0.0003(3) 0.0001(3) 0.0029(3) C17 0.0109(4) 0.0122(4) 0.0136(4) 0.0003(3) 0.0010(3) 0.0002(3) C20 0.0138(4) 0.0211(5) 0.0150(5) -0.0003(4) -0.0027(4) -0.0018(4) C19 0.0147(5) 0.0177(5) 0.0177(5) -0.0027(4) -0.0005(4) -0.0049(4) C18 0.0145(4) 0.0125(4) 0.0182(5) -0.0006(3) 0.0007(4) -0.0019(4) C21 0.0136(4) 0.0155(4) 0.0139(4) 0.0000(3) -0.0022(4) 0.0014(4) C22 0.0097(4) 0.0129(4) 0.0123(4) -0.0001(3) -0.0006(3) -0.0004(3) C23 0.0110(4) 0.0127(4) 0.0116(4) 0.0008(3) -0.0014(3) 0.0016(3) C24 0.0117(4) 0.0184(5) 0.0151(5) 0.0012(3) 0.0004(3) 0.0036(4) C26 0.0277(6) 0.0344(7) 0.0136(5) 0.0122(5) -0.0001(4) -0.0037(5) C27 0.0314(6) 0.0231(6) 0.0183(5) 0.0037(5) -0.0041(5) -0.0076(4) C28 0.0208(5) 0.0151(4) 0.0161(5) -0.0008(4) -0.0023(4) -0.0005(4) C25 0.0143(5) 0.0320(6) 0.0149(5) 0.0054(4) 0.0031(4) 0.0059(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 N3 . 1.6120(11) ? S1 N4 . 1.6146(12) ? N1 C1 . 1.3973(13) ? N1 C8 . 1.4058(13) ? N1 P1 . 1.6992(12) ? C1 C2 . 1.3933(14) ? C1 C6 . 1.4061(15) ? P1 N2 . 1.6943(11) ? P1 C23 . 1.8163(12) ? C2 C3 . 1.3863(15) ? C2 H2 . 0.95 ? N2 C22 . 1.3977(13) ? N2 C15 . 1.4030(13) ? N3 C11 . 1.3509(14) ? C3 C4 . 1.4050(17) ? C3 H3 . 0.95 ? N4 C12 . 1.3479(14) ? C4 C5 . 1.3779(16) ? C4 H4 . 0.95 ? C6 C5 . 1.4023(14) ? C6 C7 . 1.4261(15) ? C5 H5 . 0.95 ? C9 C10 . 1.3816(15) ? C9 C14 . 1.4584(14) ? C9 C8 . 1.4713(14) ? C8 C7 . 1.3719(14) ? C7 H7 . 0.95 ? C10 C11 . 1.4071(15) ? C10 H10 . 0.95 ? C11 C12 . 1.4243(15) ? C12 C13 . 1.4076(15) ? C16 C15 . 1.3699(15) ? C16 C17 . 1.4300(15) ? C16 H16 . 0.95 ? C15 C14 . 1.4680(14) ? C14 C13 . 1.3830(14) ? C13 H13 . 0.95 ? C17 C18 . 1.4011(15) ? C17 C22 . 1.4073(15) ? C20 C21 . 1.3830(15) ? C20 C19 . 1.4051(17) ? C20 H20 . 0.95 ? C19 C18 . 1.3840(16) ? C19 H19 . 0.95 ? C18 H18 . 0.95 ? C21 C22 . 1.3912(15) ? C21 H21 . 0.95 ? C23 C24 . 1.3945(15) ? C23 C28 . 1.3979(15) ? C24 C25 . 1.3812(16) ? C24 H24 . 0.95 ? C26 C27 . 1.388(2) ? C26 C25 . 1.391(2) ? C26 H26 . 0.95 ? C27 C28 . 1.3883(17) ? C27 H27 . 0.95 ? C28 H28 . 0.95 ? C25 H25 . 0.95 ? 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 N3 S1 N4 . . 101.84(5) ? C1 N1 C8 . . 107.87(9) ? C1 N1 P1 . . 121.07(7) ? C8 N1 P1 . . 130.97(7) ? C2 C1 N1 . . 129.16(10) ? C2 C1 C6 . . 122.69(9) ? N1 C1 C6 . . 108.14(9) ? N2 P1 N1 . . 100.41(4) ? N2 P1 C23 . . 101.98(5) ? N1 P1 C23 . . 102.99(5) ? C3 C2 C1 . . 117.07(10) ? C3 C2 H2 . . 121.5 ? C1 C2 H2 . . 121.5 ? C22 N2 C15 . . 107.98(8) ? C22 N2 P1 . . 122.71(7) ? C15 N2 P1 . . 128.92(7) ? C11 N3 S1 . . 105.38(8) ? C2 C3 C4 . . 121.07(10) ? C2 C3 H3 . . 119.5 ? C4 C3 H3 . . 119.5 ? C12 N4 S1 . . 105.58(8) ? C5 C4 C3 . . 121.43(10) ? C5 C4 H4 . . 119.3 ? C3 C4 H4 . . 119.3 ? C5 C6 C1 . . 118.98(10) ? C5 C6 C7 . . 134.03(10) ? C1 C6 C7 . . 106.97(9) ? C4 C5 C6 . . 118.71(10) ? C4 C5 H5 . . 120.6 ? C6 C5 H5 . . 120.6 ? C10 C9 C14 . . 119.40(9) ? C10 C9 C8 . . 114.21(9) ? C14 C9 C8 . . 126.26(9) ? C7 C8 N1 . . 108.77(9) ? C7 C8 C9 . . 126.11(9) ? N1 C8 C9 . . 125.11(9) ? C8 C7 C6 . . 108.21(9) ? C8 C7 H7 . . 125.9 ? C6 C7 H7 . . 125.9 ? C9 C10 C11 . . 120.38(10) ? C9 C10 H10 . . 119.8 ? C11 C10 H10 . . 119.8 ? N3 C11 C10 . . 126.31(10) ? N3 C11 C12 . . 113.73(9) ? C10 C11 C12 . . 119.96(9) ? N4 C12 C13 . . 126.60(10) ? N4 C12 C11 . . 113.46(10) ? C13 C12 C11 . . 119.88(9) ? C15 C16 C17 . . 108.35(9) ? C15 C16 H16 . . 125.8 ? C17 C16 H16 . . 125.8 ? C16 C15 N2 . . 108.79(9) ? C16 C15 C14 . . 125.96(9) ? N2 C15 C14 . . 125.22(9) ? C13 C14 C9 . . 119.98(9) ? C13 C14 C15 . . 114.36(9) ? C9 C14 C15 . . 125.19(9) ? C14 C13 C12 . . 120.04(10) ? C14 C13 H13 . . 120.0 ? C12 C13 H13 . . 120.0 ? C18 C17 C22 . . 119.17(10) ? C18 C17 C16 . . 134.14(10) ? C22 C17 C16 . . 106.68(9) ? C21 C20 C19 . . 121.23(10) ? C21 C20 H20 . . 119.4 ? C19 C20 H20 . . 119.4 ? C18 C19 C20 . . 121.18(10) ? C18 C19 H19 . . 119.4 ? C20 C19 H19 . . 119.4 ? C19 C18 C17 . . 118.60(10) ? C19 C18 H18 . . 120.7 ? C17 C18 H18 . . 120.7 ? C20 C21 C22 . . 117.28(10) ? C20 C21 H21 . . 121.4 ? C22 C21 H21 . . 121.4 ? C21 C22 N2 . . 129.25(9) ? C21 C22 C17 . . 122.53(9) ? N2 C22 C17 . . 108.19(9) ? C24 C23 C28 . . 119.08(10) ? C24 C23 P1 . . 120.62(8) ? C28 C23 P1 . . 118.86(8) ? C25 C24 C23 . . 120.32(11) ? C25 C24 H24 . . 119.8 ? C23 C24 H24 . . 119.8 ? C27 C26 C25 . . 119.55(11) ? C27 C26 H26 . . 120.2 ? C25 C26 H26 . . 120.2 ? C26 C27 C28 . . 120.15(12) ? C26 C27 H27 . . 119.9 ? C28 C27 H27 . . 119.9 ? C27 C28 C23 . . 120.36(11) ? C27 C28 H28 . . 119.8 ? C23 C28 H28 . . 119.8 ? C24 C25 C26 . . 120.53(11) ? C24 C25 H25 . . 119.7 ? C26 C25 H25 . . 119.7 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C8 N1 C1 C2 . . . . 176.75(10) ? P1 N1 C1 C2 . . . . -0.18(15) ? C8 N1 C1 C6 . . . . -1.93(11) ? P1 N1 C1 C6 . . . . -178.86(7) ? C1 N1 P1 N2 . . . . 127.98(8) ? C8 N1 P1 N2 . . . . -48.14(10) ? C1 N1 P1 C23 . . . . -127.02(8) ? C8 N1 P1 C23 . . . . 56.86(10) ? N1 C1 C2 C3 . . . . 179.65(10) ? C6 C1 C2 C3 . . . . -1.84(16) ? N1 P1 N2 C22 . . . . -129.64(8) ? C23 P1 N2 C22 . . . . 124.55(9) ? N1 P1 N2 C15 . . . . 58.43(10) ? C23 P1 N2 C15 . . . . -47.39(10) ? N4 S1 N3 C11 . . . . -0.10(9) ? C1 C2 C3 C4 . . . . 0.06(16) ? N3 S1 N4 C12 . . . . 0.58(8) ? C2 C3 C4 C5 . . . . 1.37(17) ? C2 C1 C6 C5 . . . . 2.20(15) ? N1 C1 C6 C5 . . . . -179.02(9) ? C2 C1 C6 C7 . . . . -176.85(10) ? N1 C1 C6 C7 . . . . 1.93(11) ? C3 C4 C5 C6 . . . . -1.01(16) ? C1 C6 C5 C4 . . . . -0.71(15) ? C7 C6 C5 C4 . . . . 178.03(11) ? C1 N1 C8 C7 . . . . 1.18(11) ? P1 N1 C8 C7 . . . . 177.70(8) ? C1 N1 C8 C9 . . . . 179.62(9) ? P1 N1 C8 C9 . . . . -3.87(15) ? C10 C9 C8 C7 . . . . 26.65(15) ? C14 C9 C8 C7 . . . . -149.21(11) ? C10 C9 C8 N1 . . . . -151.52(10) ? C14 C9 C8 N1 . . . . 32.62(16) ? N1 C8 C7 C6 . . . . 0.02(11) ? C9 C8 C7 C6 . . . . -178.40(9) ? C5 C6 C7 C8 . . . . 179.95(11) ? C1 C6 C7 C8 . . . . -1.21(11) ? C14 C9 C10 C11 . . . . 0.68(15) ? C8 C9 C10 C11 . . . . -175.49(9) ? S1 N3 C11 C10 . . . . 179.21(9) ? S1 N3 C11 C12 . . . . -0.41(11) ? C9 C10 C11 N3 . . . . 175.55(10) ? C9 C10 C11 C12 . . . . -4.85(16) ? S1 N4 C12 C13 . . . . 176.30(9) ? S1 N4 C12 C11 . . . . -0.88(11) ? N3 C11 C12 N4 . . . . 0.89(14) ? C10 C11 C12 N4 . . . . -178.75(10) ? N3 C11 C12 C13 . . . . -176.50(10) ? C10 C11 C12 C13 . . . . 3.86(15) ? C17 C16 C15 N2 . . . . 1.27(12) ? C17 C16 C15 C14 . . . . -176.93(9) ? C22 N2 C15 C16 . . . . -1.58(11) ? P1 N2 C15 C16 . . . . 171.29(8) ? C22 N2 C15 C14 . . . . 176.64(9) ? P1 N2 C15 C14 . . . . -10.49(15) ? C10 C9 C14 C13 . . . . 4.61(15) ? C8 C9 C14 C13 . . . . -179.73(10) ? C10 C9 C14 C15 . . . . -167.11(10) ? C8 C9 C14 C15 . . . . 8.56(16) ? C16 C15 C14 C13 . . . . -31.23(15) ? N2 C15 C14 C13 . . . . 150.85(10) ? C16 C15 C14 C9 . . . . 140.89(11) ? N2 C15 C14 C9 . . . . -37.03(15) ? C9 C14 C13 C12 . . . . -5.60(15) ? C15 C14 C13 C12 . . . . 166.97(9) ? N4 C12 C13 C14 . . . . -175.59(10) ? C11 C12 C13 C14 . . . . 1.43(15) ? C15 C16 C17 C18 . . . . 177.76(11) ? C15 C16 C17 C22 . . . . -0.49(12) ? C21 C20 C19 C18 . . . . -0.48(17) ? C20 C19 C18 C17 . . . . 0.50(16) ? C22 C17 C18 C19 . . . . 0.11(15) ? C16 C17 C18 C19 . . . . -177.96(11) ? C19 C20 C21 C22 . . . . -0.17(16) ? C20 C21 C22 N2 . . . . 178.67(10) ? C20 C21 C22 C17 . . . . 0.81(16) ? C15 N2 C22 C21 . . . . -176.84(10) ? P1 N2 C22 C21 . . . . 9.75(16) ? C15 N2 C22 C17 . . . . 1.26(11) ? P1 N2 C22 C17 . . . . -172.15(7) ? C18 C17 C22 C21 . . . . -0.79(16) ? C16 C17 C22 C21 . . . . 177.77(10) ? C18 C17 C22 N2 . . . . -179.04(9) ? C16 C17 C22 N2 . . . . -0.49(11) ? N2 P1 C23 C24 . . . . -36.73(9) ? N1 P1 C23 C24 . . . . -140.53(8) ? N2 P1 C23 C28 . . . . 157.07(8) ? N1 P1 C23 C28 . . . . 53.27(9) ? C28 C23 C24 C25 . . . . 0.57(16) ? P1 C23 C24 C25 . . . . -165.59(8) ? C25 C26 C27 C28 . . . . 0.05(19) ? C26 C27 C28 C23 . . . . 0.78(18) ? C24 C23 C28 C27 . . . . -1.09(16) ? P1 C23 C28 C27 . . . . 165.32(9) ? C23 C24 C25 C26 . . . . 0.26(17) ? C27 C26 C25 C24 . . . . -0.58(18) ? _shelx_res_file ; mo_PDJYR4_0ma.res created by SHELXL-2014/7 TITL mo_PDJYR4_0ma in Pccn CELL 0.71073 17.0079 32.2434 7.6880 90.000 90.000 90.000 ZERR 8.00 0.0077 0.0118 0.0031 0.000 0.000 0.000 LATT 1 SYMM x+1/2, -y, -z+1/2 SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y+1/2, z SFAC C H N P S UNIT 224 136 32 8 8 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -173.140 SIZE 0.148 0.171 0.358 ACTA L.S. 10 FMAP 2 PLAN -5 0 0.00 HTAB BOND $H CONF WGHT 0.056500 2.121000 FVAR 0.07356 S1 5 0.639522 0.066566 0.738636 11.00000 0.02465 0.01805 = 0.01040 0.00265 -0.00452 -0.00027 N1 3 0.521036 0.156154 -0.086769 11.00000 0.01048 0.01317 = 0.01073 0.00418 0.00018 -0.00040 C1 1 0.557194 0.179336 -0.217847 11.00000 0.01237 0.01056 = 0.01088 0.00134 0.00144 0.00038 P1 4 0.422750 0.146742 -0.090597 11.00000 0.00966 0.01049 = 0.01065 0.00223 -0.00050 -0.00001 C2 1 0.523882 0.197656 -0.364510 11.00000 0.01425 0.01545 = 0.01313 0.00424 0.00022 0.00030 AFIX 43 H2 2 0.469256 0.195386 -0.388473 11.00000 -1.20000 AFIX 0 N2 3 0.422245 0.094500 -0.066872 11.00000 0.01245 0.01004 = 0.01170 0.00158 -0.00230 -0.00025 N3 3 0.671378 0.099711 0.598364 11.00000 0.02286 0.01586 = 0.01216 0.00141 -0.00462 -0.00106 C3 1 0.573951 0.219341 -0.473931 11.00000 0.01823 0.01642 = 0.01304 0.00431 0.00124 0.00005 AFIX 43 H3 2 0.553341 0.232274 -0.575165 11.00000 -1.20000 AFIX 0 N4 3 0.560452 0.049884 0.645837 11.00000 0.02007 0.01908 = 0.01063 0.00380 -0.00048 0.00080 C4 1 0.654681 0.222502 -0.437545 11.00000 0.01753 0.01595 = 0.01445 0.00237 0.00411 -0.00238 AFIX 43 H4 2 0.687438 0.238066 -0.513421 11.00000 -1.20000 AFIX 0 C6 1 0.638162 0.181193 -0.181707 11.00000 0.01216 0.01113 = 0.01056 -0.00051 0.00145 -0.00061 C5 1 0.687373 0.203516 -0.294187 11.00000 0.01330 0.01480 = 0.01372 0.00019 0.00290 -0.00173 AFIX 43 H5 2 0.742190 0.205510 -0.271981 11.00000 -1.20000 AFIX 0 C9 1 0.566350 0.117168 0.184393 11.00000 0.01242 0.01070 = 0.00969 0.00117 -0.00032 0.00053 C8 1 0.579939 0.142420 0.027844 11.00000 0.01127 0.01092 = 0.00981 0.00086 -0.00080 0.00003 C7 1 0.651115 0.157346 -0.028133 11.00000 0.01196 0.01321 = 0.01118 0.00053 -0.00072 -0.00058 AFIX 43 H7 2 0.700505 0.152612 0.026058 11.00000 -1.20000 AFIX 0 C10 1 0.621188 0.123103 0.314623 11.00000 0.01617 0.01262 = 0.01125 0.00148 -0.00198 -0.00137 AFIX 43 H10 2 0.660770 0.143649 0.301348 11.00000 -1.20000 AFIX 0 C11 1 0.618749 0.098892 0.466799 11.00000 0.01690 0.01237 = 0.01054 -0.00019 -0.00128 0.00065 C12 1 0.556017 0.070310 0.493176 11.00000 0.01551 0.01344 = 0.01015 0.00202 0.00024 0.00192 C16 1 0.429738 0.030155 0.046670 11.00000 0.01290 0.01155 = 0.01354 0.00196 0.00028 -0.00009 AFIX 43 H16 2 0.441950 0.007642 0.121667 11.00000 -1.20000 AFIX 0 C15 1 0.453535 0.070411 0.068416 11.00000 0.01102 0.01191 = 0.01096 0.00212 -0.00009 0.00027 C14 1 0.505286 0.085868 0.206806 11.00000 0.01094 0.01188 = 0.01105 0.00167 -0.00009 0.00049 C13 1 0.499209 0.064520 0.362257 11.00000 0.01333 0.01457 = 0.01215 0.00294 0.00009 -0.00034 AFIX 43 H13 2 0.456670 0.045939 0.380692 11.00000 -1.20000 AFIX 0 C17 1 0.383379 0.027804 -0.108189 11.00000 0.01090 0.01217 = 0.01362 0.00022 0.00103 0.00027 C20 1 0.305054 0.044889 -0.417732 11.00000 0.01382 0.02111 = 0.01502 -0.00181 -0.00267 -0.00032 AFIX 43 H20 2 0.278172 0.050098 -0.523824 11.00000 -1.20000 AFIX 0 C19 1 0.307055 0.004355 -0.350775 11.00000 0.01474 0.01766 = 0.01769 -0.00489 -0.00047 -0.00265 AFIX 43 H19 2 0.281165 -0.017299 -0.411939 11.00000 -1.20000 AFIX 0 C18 1 0.346071 -0.004589 -0.197308 11.00000 0.01448 0.01247 = 0.01816 -0.00188 0.00068 -0.00057 AFIX 43 H18 2 0.347524 -0.032112 -0.153324 11.00000 -1.20000 AFIX 0 C21 1 0.341486 0.077346 -0.332074 11.00000 0.01362 0.01545 = 0.01386 0.00139 -0.00222 0.00005 AFIX 43 H21 2 0.340321 0.104758 -0.377293 11.00000 -1.20000 AFIX 0 C22 1 0.379911 0.068210 -0.176988 11.00000 0.00975 0.01292 = 0.01227 -0.00040 -0.00059 -0.00014 C23 1 0.390683 0.164092 0.122687 11.00000 0.01100 0.01274 = 0.01155 0.00163 -0.00143 0.00085 C24 1 0.334101 0.141881 0.215171 11.00000 0.01173 0.01845 = 0.01512 0.00359 0.00039 0.00115 AFIX 43 H24 2 0.320820 0.114496 0.180313 11.00000 -1.20000 AFIX 0 C26 1 0.315846 0.199637 0.409467 11.00000 0.02772 0.03436 = 0.01362 -0.00366 -0.00009 0.01222 AFIX 43 H26 2 0.290010 0.211718 0.506602 11.00000 -1.20000 AFIX 0 C27 1 0.372362 0.221899 0.318752 11.00000 0.03141 0.02314 = 0.01832 -0.00756 -0.00407 0.00373 AFIX 43 H27 2 0.385317 0.249306 0.353904 11.00000 -1.20000 AFIX 0 C28 1 0.410015 0.204211 0.176739 11.00000 0.02076 0.01513 = 0.01610 -0.00050 -0.00233 -0.00083 AFIX 43 H28 2 0.449132 0.219454 0.115965 11.00000 -1.20000 AFIX 0 C25 1 0.297275 0.159505 0.357208 11.00000 0.01427 0.03198 = 0.01491 0.00593 0.00306 0.00540 AFIX 43 H25 2 0.258956 0.144099 0.419724 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_PDJYR4_0ma in Pccn REM R1 = 0.0371 for 6489 Fo > 4sig(Fo) and 0.0438 for all 7382 data REM 307 parameters refined using 0 restraints END WGHT 0.0532 2.1709 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y, -z+1 HTAB C16 S1_$1 HTAB C16 N4_$1 REM Highest difference peak 0.694, deepest hole -0.244, 1-sigma level 0.075 Q1 1 0.5982 0.1815 -0.2005 11.00000 0.05 0.69 Q2 1 0.3081 0.0245 -0.3852 11.00000 0.05 0.63 Q3 1 0.3598 0.0754 -0.2488 11.00000 0.05 0.60 Q4 1 0.6127 0.2213 -0.4436 11.00000 0.05 0.59 Q5 1 0.4417 0.0506 0.0633 11.00000 0.05 0.59 ; _shelx_res_checksum 6571 ####################################################################### # # 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_I _database_code_depnum_ccdc_archive 'CCDC 1427667' _audit_update_record ; 2015-09-25 deposited with the CCDC. 2016-03-15 downloaded from the CCDC. ; _chemical_name_systematic ? _chemical_name_common YR3 _chemical_formula_moiety ? _chemical_formula_sum 'C28 H19 N2 P' _chemical_formula_iupac ? _chemical_formula_weight 414.44 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' 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 8.5379(4) _cell_length_b 12.3661(6) _cell_length_c 20.2417(10) _cell_angle_alpha 90 _cell_angle_beta 99.9180(10) _cell_angle_gamma 90 _cell_volume 2105.19(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9904 _cell_measurement_theta_min 4.2066 _cell_measurement_theta_max 72.2067 _cell_measurement_temperature 100.(2) _exptl_crystal_description rod _exptl_crystal_colour ? _exptl_crystal_size_max 0.381 _exptl_crystal_size_mid 0.163 _exptl_crystal_size_min 0.082 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.284 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/2 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.90 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'ImuS micro--focus source' _diffrn_source_type ? _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'BRUKER APEX II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.4167 _diffrn_reflns_number 34226 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_unetI/netI 0.0219 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 72.21 _diffrn_reflns_theta_full 72.21 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _refine_special_details ; ; _reflns_number_total 4150 _reflns_number_gt 3981 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.1000 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_number_reflns 4150 _refine_ls_number_parameters 280 _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^)+(0.0575P)^2^+0.9597P] 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 0.045 _refine_ls_shift/su_mean 0.007 _refine_diff_density_max 0.456 _refine_diff_density_min -0.309 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v4.2.4' _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? 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 P P1 0.50699(4) 0.66719(2) 0.08528(2) 0.01391(11) Uani d . . . 1 . . N N1 0.45373(12) 0.78218(8) 0.12308(5) 0.0149(2) Uani d . . . 1 . . C C1 0.36398(14) 0.86484(10) 0.08786(6) 0.0158(3) Uani d . . . 1 . . C C2 0.28687(16) 0.86777(11) 0.02119(7) 0.0200(3) Uani d . . . 1 . . H H2 0.2887 0.8075 -0.0078 0.024 Uiso calc U . R 1 . . N N2 0.45774(13) 0.57174(8) 0.13957(5) 0.0156(2) Uani d . . . 1 . . C C3 0.20786(17) 0.96204(12) -0.00081(7) 0.0240(3) Uani d . . . 1 . . H H3 0.1551 0.9668 -0.046 0.029 Uiso calc U . R 1 . . C C4 0.20370(18) 1.05097(11) 0.04206(7) 0.0252(3) Uani d . . . 1 . . H H4 0.1483 1.1146 0.0253 0.03 Uiso calc U . R 1 . . C C6 0.36146(15) 0.95286(10) 0.13179(6) 0.0182(3) Uani d . . . 1 . . C C5 0.27885(17) 1.04740(11) 0.10809(7) 0.0228(3) Uani d . . . 1 . . H H5 0.2749 1.1076 0.1369 0.027 Uiso calc U . R 1 . . C C9 0.61446(15) 0.75714(11) 0.24053(6) 0.0162(3) Uani d . . . 1 . . C C8 0.50893(15) 0.81958(10) 0.18876(6) 0.0160(3) Uani d . . . 1 . . C C7 0.45340(16) 0.92214(10) 0.19472(6) 0.0187(3) Uani d . . . 1 . . H H7 0.4727 0.9656 0.234 0.022 Uiso calc U . R 1 . . C C10 0.72583(16) 0.81734(11) 0.28455(7) 0.0202(3) Uani d . . . 1 . . H H10 0.7324 0.8931 0.2777 0.024 Uiso calc U . R 1 . . C C11 0.82695(16) 0.77013(12) 0.33781(7) 0.0227(3) Uani d . . . 1 . . H H11 0.9012 0.8131 0.3669 0.027 Uiso calc U . R 1 . . C C12 0.81853(17) 0.65943(12) 0.34815(7) 0.0220(3) Uani d . . . 1 . . H H12 0.8866 0.6261 0.3845 0.026 Uiso calc U . R 1 . . C C13 0.71016(16) 0.59801(11) 0.30499(6) 0.0197(3) Uani d . . . 1 . . H H13 0.7054 0.5223 0.3124 0.024 Uiso calc U . R 1 . . C C14 0.60708(15) 0.64395(11) 0.25066(6) 0.0166(3) Uani d . . . 1 . . C C21 0.26926(16) 0.46112(11) 0.05540(7) 0.0201(3) Uani d . . . 1 . . H H21 0.2876 0.4996 0.0168 0.024 Uiso calc U . R 1 . . C C20 0.16176(17) 0.37639(11) 0.05021(7) 0.0233(3) Uani d . . . 1 . . H H20 0.1039 0.3574 0.0074 0.028 Uiso calc U . R 1 . . C C19 0.13654(17) 0.31790(11) 0.10707(7) 0.0226(3) Uani d . . . 1 . . H H19 0.0621 0.2601 0.1021 0.027 Uiso calc U . R 1 . . C C18 0.21869(16) 0.34342(10) 0.17018(7) 0.0205(3) Uani d . . . 1 . . H H18 0.2034 0.3024 0.2083 0.025 Uiso calc U . R 1 . . C C17 0.32487(15) 0.43085(10) 0.17691(7) 0.0174(3) Uani d . . . 1 . . C C16 0.41771(15) 0.48392(10) 0.23319(6) 0.0181(3) Uani d . . . 1 . . H H16 0.4242 0.4635 0.2788 0.022 Uiso calc U . R 1 . . C C15 0.49536(15) 0.56888(10) 0.21029(6) 0.0162(3) Uani d . . . 1 . . C C22 0.34955(15) 0.48789(10) 0.11920(6) 0.0162(3) Uani d . . . 1 . . C C23 0.72217(15) 0.67620(10) 0.10940(6) 0.0151(3) Uani d . . . 1 . . C C24 0.79639(16) 0.77591(11) 0.10444(6) 0.0186(3) Uani d . . . 1 . . H H24 0.7338 0.8387 0.0923 0.022 Uiso calc U . R 1 . . C C25 0.96091(16) 0.78371(12) 0.11708(7) 0.0223(3) Uani d . . . 1 . . H H25 1.0108 0.8516 0.1136 0.027 Uiso calc U . R 1 . . C C28 0.81502(16) 0.58399(11) 0.12524(6) 0.0195(3) Uani d . . . 1 . . H H28 0.7656 0.5155 0.1271 0.023 Uiso calc U . R 1 . . C C27 0.97964(17) 0.59210(12) 0.13835(7) 0.0250(3) Uani d . . . 1 . . H H27 1.0426 0.5293 0.1498 0.03 Uiso calc U . R 1 . . C C26 1.05255(17) 0.69201(13) 0.13479(7) 0.0253(3) Uani d . . . 1 . . H H26 1.1652 0.6975 0.1445 0.03 Uiso calc U . R 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 P1 0.01563(18) 0.01358(18) 0.01368(17) 0.00098(11) 0.00581(12) 0.00032(10) N1 0.0159(5) 0.0152(5) 0.0145(5) 0.0014(4) 0.0047(4) 0.0003(4) C1 0.0147(6) 0.0151(6) 0.0191(6) 0.0016(5) 0.0074(5) 0.0027(5) C2 0.0215(6) 0.0203(6) 0.0188(6) 0.0026(5) 0.0053(5) 0.0002(5) N2 0.0174(5) 0.0154(5) 0.0151(5) -0.0006(4) 0.0059(4) 0.0002(4) C3 0.0261(7) 0.0257(7) 0.0201(6) 0.0060(6) 0.0034(5) 0.0043(5) C4 0.0284(7) 0.0201(7) 0.0279(7) 0.0086(6) 0.0066(6) 0.0056(5) C6 0.0195(6) 0.0170(6) 0.0196(6) 0.0004(5) 0.0075(5) 0.0004(5) C5 0.0272(7) 0.0169(6) 0.0256(7) 0.0050(5) 0.0083(5) 0.0002(5) C9 0.0167(6) 0.0192(6) 0.0144(6) 0.0013(5) 0.0075(5) 0.0004(5) C8 0.0172(6) 0.0169(6) 0.0152(6) -0.0017(5) 0.0068(5) -0.0007(5) C7 0.0217(6) 0.0172(6) 0.0181(6) 0.0008(5) 0.0064(5) -0.0010(5) C10 0.0223(7) 0.0201(6) 0.0193(6) -0.0018(5) 0.0065(5) -0.0001(5) C11 0.0218(6) 0.0288(7) 0.0174(6) -0.0034(6) 0.0030(5) -0.0023(5) C12 0.0209(6) 0.0291(7) 0.0161(6) 0.0038(5) 0.0040(5) 0.0020(5) C13 0.0216(6) 0.0205(6) 0.0182(6) 0.0032(5) 0.0067(5) 0.0021(5) C14 0.0171(6) 0.0192(6) 0.0153(6) 0.0015(5) 0.0077(5) 0.0001(5) C21 0.0242(7) 0.0187(6) 0.0194(6) -0.0008(5) 0.0087(5) -0.0025(5) C20 0.0266(7) 0.0211(7) 0.0235(7) -0.0026(5) 0.0081(5) -0.0076(5) C19 0.0243(7) 0.0148(6) 0.0312(7) -0.0028(5) 0.0119(6) -0.0049(5) C18 0.0233(7) 0.0141(6) 0.0270(7) 0.0016(5) 0.0123(5) 0.0018(5) C17 0.0181(6) 0.0146(6) 0.0211(6) 0.0041(5) 0.0081(5) 0.0014(5) C16 0.0194(6) 0.0173(6) 0.0187(6) 0.0024(5) 0.0061(5) 0.0033(5) C15 0.0174(6) 0.0171(6) 0.0149(6) 0.0041(5) 0.0056(5) 0.0022(5) C22 0.0164(6) 0.0129(6) 0.0211(6) 0.0015(5) 0.0082(5) -0.0006(5) C23 0.0164(6) 0.0177(6) 0.0127(6) 0.0011(5) 0.0065(4) -0.0005(4) C24 0.0209(6) 0.0169(6) 0.0199(6) 0.0012(5) 0.0090(5) -0.0010(5) C25 0.0222(7) 0.0246(7) 0.0224(6) -0.0053(5) 0.0102(5) -0.0050(5) C28 0.0225(6) 0.0186(6) 0.0199(6) 0.0032(5) 0.0102(5) 0.0042(5) C27 0.0219(7) 0.0309(8) 0.0243(7) 0.0093(6) 0.0097(5) 0.0083(6) C26 0.0166(6) 0.0387(8) 0.0220(7) 0.0004(6) 0.0066(5) 0.0004(6) _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 P1 N2 . 1.7136(11) ? P1 N1 . 1.7130(11) ? P1 C23 . 1.8212(13) ? N1 C1 . 1.3972(16) ? N1 C8 . 1.4099(16) ? C1 C2 . 1.3963(18) ? C1 C6 . 1.4080(18) ? C2 C3 . 1.3816(19) ? C2 H2 . 0.95 ? N2 C22 . 1.4026(16) ? N2 C15 . 1.4126(16) ? C3 C4 . 1.405(2) ? C3 H3 . 0.95 ? C4 C5 . 1.380(2) ? C4 H4 . 0.95 ? C6 C5 . 1.4064(18) ? C6 C7 . 1.4278(18) ? C5 H5 . 0.95 ? C9 C10 . 1.4002(19) ? C9 C14 . 1.4176(18) ? C9 C8 . 1.4767(17) ? C8 C7 . 1.3665(18) ? C7 H7 . 0.95 ? C10 C11 . 1.3884(19) ? C10 H10 . 0.95 ? C11 C12 . 1.389(2) ? C11 H11 . 0.95 ? C12 C13 . 1.385(2) ? C12 H12 . 0.95 ? C13 C14 . 1.4048(18) ? C13 H13 . 0.95 ? C14 C15 . 1.4734(18) ? C21 C20 . 1.3850(19) ? C21 C22 . 1.3937(18) ? C21 H21 . 0.95 ? C20 C19 . 1.407(2) ? C20 H20 . 0.95 ? C19 C18 . 1.384(2) ? C19 H19 . 0.95 ? C18 C17 . 1.4025(19) ? C18 H18 . 0.95 ? C17 C22 . 1.4111(18) ? C17 C16 . 1.4303(18) ? C16 C15 . 1.3653(18) ? C16 H16 . 0.95 ? C23 C28 . 1.3943(18) ? C23 C24 . 1.3978(18) ? C24 C25 . 1.3871(19) ? C24 H24 . 0.95 ? C25 C26 . 1.389(2) ? C25 H25 . 0.95 ? C28 C27 . 1.388(2) ? C28 H28 . 0.95 ? C27 C26 . 1.391(2) ? C27 H27 . 0.95 ? C26 H26 . 0.95 ? 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 N2 P1 N1 . . 99.91(5) ? N2 P1 C23 . . 102.59(5) ? N1 P1 C23 . . 99.36(5) ? C1 N1 C8 . . 107.82(10) ? C1 N1 P1 . . 122.95(9) ? C8 N1 P1 . . 128.48(9) ? C2 C1 N1 . . 129.64(12) ? C2 C1 C6 . . 122.30(12) ? N1 C1 C6 . . 108.06(11) ? C3 C2 C1 . . 117.14(12) ? C3 C2 H2 . . 121.4 ? C1 C2 H2 . . 121.4 ? C22 N2 C15 . . 107.62(10) ? C22 N2 P1 . . 122.87(9) ? C15 N2 P1 . . 128.98(9) ? C2 C3 C4 . . 121.62(13) ? C2 C3 H3 . . 119.2 ? C4 C3 H3 . . 119.2 ? C5 C4 C3 . . 121.07(13) ? C5 C4 H4 . . 119.5 ? C3 C4 H4 . . 119.5 ? C5 C6 C1 . . 119.24(12) ? C5 C6 C7 . . 133.78(12) ? C1 C6 C7 . . 106.97(11) ? C4 C5 C6 . . 118.63(13) ? C4 C5 H5 . . 120.7 ? C6 C5 H5 . . 120.7 ? C10 C9 C14 . . 118.36(12) ? C10 C9 C8 . . 115.98(12) ? C14 C9 C8 . . 125.59(12) ? C7 C8 N1 . . 108.84(11) ? C7 C8 C9 . . 126.96(12) ? N1 C8 C9 . . 124.17(11) ? C8 C7 C6 . . 108.30(11) ? C8 C7 H7 . . 125.8 ? C6 C7 H7 . . 125.8 ? C11 C10 C9 . . 122.28(13) ? C11 C10 H10 . . 118.9 ? C9 C10 H10 . . 118.9 ? C10 C11 C12 . . 119.35(13) ? C10 C11 H11 . . 120.3 ? C12 C11 H11 . . 120.3 ? C13 C12 C11 . . 119.47(13) ? C13 C12 H12 . . 120.3 ? C11 C12 H12 . . 120.3 ? C12 C13 C14 . . 122.17(13) ? C12 C13 H13 . . 118.9 ? C14 C13 H13 . . 118.9 ? C13 C14 C9 . . 118.37(12) ? C13 C14 C15 . . 115.96(12) ? C9 C14 C15 . . 125.63(12) ? C20 C21 C22 . . 117.63(12) ? C20 C21 H21 . . 121.2 ? C22 C21 H21 . . 121.2 ? C21 C20 C19 . . 121.31(13) ? C21 C20 H20 . . 119.3 ? C19 C20 H20 . . 119.3 ? C18 C19 C20 . . 120.88(13) ? C18 C19 H19 . . 119.6 ? C20 C19 H19 . . 119.6 ? C19 C18 C17 . . 118.81(12) ? C19 C18 H18 . . 120.6 ? C17 C18 H18 . . 120.6 ? C18 C17 C22 . . 119.41(12) ? C18 C17 C16 . . 133.74(12) ? C22 C17 C16 . . 106.78(11) ? C15 C16 C17 . . 108.52(11) ? C15 C16 H16 . . 125.7 ? C17 C16 H16 . . 125.7 ? C16 C15 N2 . . 108.93(11) ? C16 C15 C14 . . 127.04(11) ? N2 C15 C14 . . 123.97(11) ? C21 C22 N2 . . 129.93(12) ? C21 C22 C17 . . 121.91(12) ? N2 C22 C17 . . 108.11(11) ? C28 C23 C24 . . 119.42(12) ? C28 C23 P1 . . 121.26(10) ? C24 C23 P1 . . 118.92(10) ? C25 C24 C23 . . 120.35(12) ? C25 C24 H24 . . 119.8 ? C23 C24 H24 . . 119.8 ? C24 C25 C26 . . 119.89(13) ? C24 C25 H25 . . 120.1 ? C26 C25 H25 . . 120.1 ? C27 C28 C23 . . 120.11(13) ? C27 C28 H28 . . 119.9 ? C23 C28 H28 . . 119.9 ? C26 C27 C28 . . 120.11(13) ? C26 C27 H27 . . 119.9 ? C28 C27 H27 . . 119.9 ? C27 C26 C25 . . 120.08(13) ? C27 C26 H26 . . 120.0 ? C25 C26 H26 . . 120.0 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 P1 N1 C1 . . . . -133.02(10) ? C23 P1 N1 C1 . . . . 122.33(10) ? N2 P1 N1 C8 . . . . 58.17(11) ? C23 P1 N1 C8 . . . . -46.48(12) ? C8 N1 C1 C2 . . . . 178.85(13) ? P1 N1 C1 C2 . . . . 8.03(19) ? C8 N1 C1 C6 . . . . -0.82(13) ? P1 N1 C1 C6 . . . . -171.64(9) ? N1 C1 C2 C3 . . . . -179.01(12) ? C6 C1 C2 C3 . . . . 0.62(19) ? N1 P1 N2 C22 . . . . 122.09(10) ? C23 P1 N2 C22 . . . . -135.90(10) ? N1 P1 N2 C15 . . . . -48.39(12) ? C23 P1 N2 C15 . . . . 53.62(12) ? C1 C2 C3 C4 . . . . -0.6(2) ? C2 C3 C4 C5 . . . . 0.0(2) ? C2 C1 C6 C5 . . . . -0.09(19) ? N1 C1 C6 C5 . . . . 179.61(11) ? C2 C1 C6 C7 . . . . -179.18(12) ? N1 C1 C6 C7 . . . . 0.52(14) ? C3 C4 C5 C6 . . . . 0.5(2) ? C1 C6 C5 C4 . . . . -0.5(2) ? C7 C6 C5 C4 . . . . 178.29(14) ? C1 N1 C8 C7 . . . . 0.82(14) ? P1 N1 C8 C7 . . . . 170.98(9) ? C1 N1 C8 C9 . . . . -177.08(11) ? P1 N1 C8 C9 . . . . -6.93(18) ? C10 C9 C8 C7 . . . . -32.61(18) ? C14 C9 C8 C7 . . . . 144.49(14) ? C10 C9 C8 N1 . . . . 144.90(12) ? C14 C9 C8 N1 . . . . -37.99(19) ? N1 C8 C7 C6 . . . . -0.49(14) ? C9 C8 C7 C6 . . . . 177.34(12) ? C5 C6 C7 C8 . . . . -178.92(14) ? C1 C6 C7 C8 . . . . -0.02(15) ? C14 C9 C10 C11 . . . . -0.80(19) ? C8 C9 C10 C11 . . . . 176.52(12) ? C9 C10 C11 C12 . . . . 0.1(2) ? C10 C11 C12 C13 . . . . 0.4(2) ? C11 C12 C13 C14 . . . . -0.2(2) ? C12 C13 C14 C9 . . . . -0.52(19) ? C12 C13 C14 C15 . . . . -178.35(12) ? C10 C9 C14 C13 . . . . 0.97(17) ? C8 C9 C14 C13 . . . . -176.07(11) ? C10 C9 C14 C15 . . . . 178.57(12) ? C8 C9 C14 C15 . . . . 1.5(2) ? C22 C21 C20 C19 . . . . -1.2(2) ? C21 C20 C19 C18 . . . . 0.0(2) ? C20 C19 C18 C17 . . . . 1.7(2) ? C19 C18 C17 C22 . . . . -2.28(19) ? C19 C18 C17 C16 . . . . 174.38(13) ? C18 C17 C16 C15 . . . . -177.21(14) ? C22 C17 C16 C15 . . . . -0.25(14) ? C17 C16 C15 N2 . . . . -1.08(14) ? C17 C16 C15 C14 . . . . -178.33(12) ? C22 N2 C15 C16 . . . . 2.01(14) ? P1 N2 C15 C16 . . . . 173.63(9) ? C22 N2 C15 C14 . . . . 179.36(11) ? P1 N2 C15 C14 . . . . -9.02(18) ? C13 C14 C15 C16 . . . . 38.03(18) ? C9 C14 C15 C16 . . . . -139.63(14) ? C13 C14 C15 N2 . . . . -138.83(12) ? C9 C14 C15 N2 . . . . 43.51(18) ? C20 C21 C22 N2 . . . . -176.70(13) ? C20 C21 C22 C17 . . . . 0.65(19) ? C15 N2 C22 C21 . . . . 175.49(13) ? P1 N2 C22 C21 . . . . 3.24(19) ? C15 N2 C22 C17 . . . . -2.14(13) ? P1 N2 C22 C17 . . . . -174.39(8) ? C18 C17 C22 C21 . . . . 1.11(19) ? C16 C17 C22 C21 . . . . -176.37(12) ? C18 C17 C22 N2 . . . . 178.97(11) ? C16 C17 C22 N2 . . . . 1.49(14) ? N2 P1 C23 C28 . . . . 40.84(11) ? N1 P1 C23 C28 . . . . 143.28(10) ? N2 P1 C23 C24 . . . . -146.53(10) ? N1 P1 C23 C24 . . . . -44.09(11) ? C28 C23 C24 C25 . . . . -1.89(19) ? P1 C23 C24 C25 . . . . -174.66(10) ? C23 C24 C25 C26 . . . . 0.0(2) ? C24 C23 C28 C27 . . . . 2.36(19) ? P1 C23 C28 C27 . . . . 174.95(10) ? C23 C28 C27 C26 . . . . -0.9(2) ? C28 C27 C26 C25 . . . . -1.0(2) ? C24 C25 C26 C27 . . . . 1.5(2) ? _shelx_res_file ; cu_PDJYR3_0m.res created by SHELXL-2014/7 TITL cu_PDJYR3_0m in P2(1)/n CELL 1.54178 8.5379 12.3661 20.2417 90.000 99.918 90.000 ZERR 4.00 0.0004 0.0006 0.0010 0.000 0.001 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H N P UNIT 112 76 8 4 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -173.150 SIZE 0.082 0.163 0.381 ACTA L.S. 5 FMAP 2 PLAN -56 0 0.00 HTAB BOND $H CONF WGHT 0.057500 0.959700 FVAR 0.46829 P1 4 0.506994 0.667185 0.085283 11.00000 0.01563 0.01358 = 0.01368 0.00032 0.00581 0.00098 N1 3 0.453732 0.782182 0.123082 11.00000 0.01585 0.01517 = 0.01447 0.00028 0.00469 0.00137 C1 1 0.363982 0.864843 0.087863 11.00000 0.01470 0.01514 = 0.01914 0.00270 0.00744 0.00155 C2 1 0.286873 0.867770 0.021195 11.00000 0.02145 0.02030 = 0.01880 0.00018 0.00534 0.00259 AFIX 43 H2 2 0.288663 0.807529 -0.007790 11.00000 -1.20000 AFIX 0 N2 3 0.457740 0.571742 0.139568 11.00000 0.01738 0.01541 = 0.01509 0.00024 0.00586 -0.00063 C3 1 0.207863 0.962037 -0.000806 11.00000 0.02607 0.02574 = 0.02006 0.00428 0.00339 0.00596 AFIX 43 H3 2 0.155053 0.966844 -0.046026 11.00000 -1.20000 AFIX 0 C4 1 0.203696 1.050969 0.042057 11.00000 0.02841 0.02007 = 0.02788 0.00558 0.00658 0.00861 AFIX 43 H4 2 0.148256 1.114585 0.025315 11.00000 -1.20000 AFIX 0 C6 1 0.361455 0.952860 0.131790 11.00000 0.01955 0.01700 = 0.01964 0.00042 0.00751 0.00036 C5 1 0.278845 1.047400 0.108089 11.00000 0.02721 0.01690 = 0.02564 0.00018 0.00827 0.00501 AFIX 43 H5 2 0.274853 1.107563 0.136937 11.00000 -1.20000 AFIX 0 C9 1 0.614456 0.757143 0.240525 11.00000 0.01673 0.01919 = 0.01443 0.00042 0.00747 0.00129 C8 1 0.508925 0.819579 0.188764 11.00000 0.01722 0.01693 = 0.01516 -0.00075 0.00676 -0.00166 C7 1 0.453404 0.922136 0.194720 11.00000 0.02166 0.01721 = 0.01813 -0.00101 0.00637 0.00077 AFIX 43 H7 2 0.472680 0.965555 0.234001 11.00000 -1.20000 AFIX 0 C10 1 0.725830 0.817335 0.284550 11.00000 0.02230 0.02012 = 0.01927 -0.00012 0.00651 -0.00181 AFIX 43 H10 2 0.732436 0.893093 0.277743 11.00000 -1.20000 AFIX 0 C11 1 0.826951 0.770132 0.337811 11.00000 0.02184 0.02878 = 0.01739 -0.00229 0.00297 -0.00339 AFIX 43 H11 2 0.901170 0.813146 0.366892 11.00000 -1.20000 AFIX 0 C12 1 0.818526 0.659428 0.348150 11.00000 0.02095 0.02915 = 0.01610 0.00201 0.00401 0.00377 AFIX 43 H12 2 0.886557 0.626095 0.384541 11.00000 -1.20000 AFIX 0 C13 1 0.710162 0.598005 0.304989 11.00000 0.02163 0.02047 = 0.01819 0.00208 0.00666 0.00322 AFIX 43 H13 2 0.705378 0.522299 0.312364 11.00000 -1.20000 AFIX 0 C14 1 0.607078 0.643955 0.250660 11.00000 0.01712 0.01917 = 0.01527 0.00010 0.00770 0.00148 C21 1 0.269264 0.461119 0.055399 11.00000 0.02417 0.01866 = 0.01935 -0.00247 0.00870 -0.00083 AFIX 43 H21 2 0.287624 0.499619 0.016842 11.00000 -1.20000 AFIX 0 C20 1 0.161761 0.376386 0.050212 11.00000 0.02656 0.02111 = 0.02351 -0.00756 0.00812 -0.00263 AFIX 43 H20 2 0.103900 0.357378 0.007409 11.00000 -1.20000 AFIX 0 C19 1 0.136539 0.317897 0.107074 11.00000 0.02434 0.01479 = 0.03117 -0.00486 0.01192 -0.00284 AFIX 43 H19 2 0.062111 0.260113 0.102073 11.00000 -1.20000 AFIX 0 C18 1 0.218691 0.343415 0.170182 11.00000 0.02326 0.01411 = 0.02701 0.00181 0.01231 0.00158 AFIX 43 H18 2 0.203442 0.302444 0.208267 11.00000 -1.20000 AFIX 0 C17 1 0.324870 0.430849 0.176912 11.00000 0.01807 0.01465 = 0.02106 0.00137 0.00813 0.00407 C16 1 0.417713 0.483922 0.233193 11.00000 0.01940 0.01729 = 0.01872 0.00326 0.00611 0.00239 AFIX 43 H16 2 0.424248 0.463495 0.278829 11.00000 -1.20000 AFIX 0 C15 1 0.495363 0.568881 0.210291 11.00000 0.01745 0.01714 = 0.01495 0.00219 0.00563 0.00408 C22 1 0.349547 0.487887 0.119203 11.00000 0.01637 0.01286 = 0.02107 -0.00064 0.00824 0.00151 C23 1 0.722170 0.676203 0.109400 11.00000 0.01640 0.01771 = 0.01273 -0.00046 0.00651 0.00108 C24 1 0.796386 0.775914 0.104436 11.00000 0.02091 0.01693 = 0.01988 -0.00101 0.00904 0.00118 AFIX 43 H24 2 0.733821 0.838670 0.092339 11.00000 -1.20000 AFIX 0 C25 1 0.960906 0.783707 0.117079 11.00000 0.02223 0.02463 = 0.02241 -0.00495 0.01023 -0.00531 AFIX 43 H25 2 1.010833 0.851638 0.113631 11.00000 -1.20000 AFIX 0 C28 1 0.815018 0.583986 0.125237 11.00000 0.02248 0.01862 = 0.01987 0.00421 0.01021 0.00316 AFIX 43 H28 2 0.765553 0.515492 0.127056 11.00000 -1.20000 AFIX 0 C27 1 0.979642 0.592099 0.138352 11.00000 0.02190 0.03086 = 0.02433 0.00832 0.00972 0.00932 AFIX 43 H27 2 1.042593 0.529306 0.149775 11.00000 -1.20000 AFIX 0 C26 1 1.052551 0.692008 0.134794 11.00000 0.01655 0.03866 = 0.02199 0.00036 0.00659 0.00043 AFIX 43 H26 2 1.165155 0.697548 0.144488 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM cu_PDJYR3_0m in P2(1)/n REM R1 = 0.0342 for 3981 Fo > 4sig(Fo) and 0.0358 for all 4150 data REM 280 parameters refined using 0 restraints END WGHT 0.0478 1.0800 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.456, deepest hole -0.309, 1-sigma level 0.057 Q1 1 0.6322 0.6731 0.0997 11.00000 0.05 0.46 Q2 1 0.4552 0.6190 0.1210 11.00000 0.05 0.32 Q3 1 0.7521 0.7243 0.1162 11.00000 0.05 0.32 Q4 1 0.2812 0.3968 0.1754 11.00000 0.05 0.32 Q5 1 0.4911 0.7437 0.1051 11.00000 0.05 0.31 Q6 1 0.4894 0.7936 0.1505 11.00000 0.05 0.31 Q7 1 0.4292 0.8173 0.1020 11.00000 0.05 0.31 Q8 1 0.3503 0.4510 0.2071 11.00000 0.05 0.31 Q9 1 0.9012 0.5956 0.1405 11.00000 0.05 0.30 Q10 1 0.4477 0.7237 0.1156 11.00000 0.05 0.30 Q11 1 0.6039 0.6999 0.2455 11.00000 0.05 0.30 Q12 1 0.9949 0.7429 0.1364 11.00000 0.05 0.30 Q13 1 0.8838 0.7828 0.1262 11.00000 0.05 0.29 Q14 1 0.4020 0.9436 0.1656 11.00000 0.05 0.28 Q15 1 1.0028 0.6452 0.1436 11.00000 0.05 0.28 Q16 1 0.3140 0.4588 0.1501 11.00000 0.05 0.28 Q17 1 0.3765 0.9174 0.1068 11.00000 0.05 0.27 Q18 1 0.7570 0.6369 0.1231 11.00000 0.05 0.27 Q19 1 0.5373 0.6111 0.2294 11.00000 0.05 0.26 Q20 1 0.6646 0.6241 0.2761 11.00000 0.05 0.26 Q21 1 0.5102 0.8836 0.1920 11.00000 0.05 0.26 Q22 1 0.6729 0.7823 0.2600 11.00000 0.05 0.26 Q23 1 0.3999 0.5382 0.1244 11.00000 0.05 0.26 Q24 1 0.4465 0.8570 0.1990 11.00000 0.05 0.26 Q25 1 0.4199 0.5508 0.2261 11.00000 0.05 0.26 Q26 1 0.5553 0.7865 0.2164 11.00000 0.05 0.25 Q27 1 0.4366 0.6631 0.0444 11.00000 0.05 0.25 Q28 1 0.3223 0.9988 0.1219 11.00000 0.05 0.25 Q29 1 0.4783 0.5771 0.1755 11.00000 0.05 0.22 Q30 1 0.7408 0.6387 0.3331 11.00000 0.05 0.22 Q31 1 0.4847 0.5178 0.2262 11.00000 0.05 0.21 Q32 1 0.3235 0.8622 0.0555 11.00000 0.05 0.20 Q33 1 0.2539 0.4019 0.0523 11.00000 0.05 0.20 Q34 1 0.3369 0.4618 0.0870 11.00000 0.05 0.20 Q35 1 0.1864 0.4414 0.0591 11.00000 0.05 0.20 Q36 1 0.7635 0.7941 0.3111 11.00000 0.05 0.20 Q37 1 0.1617 0.3455 0.1392 11.00000 0.05 0.19 Q38 1 0.2077 0.9039 0.0131 11.00000 0.05 0.19 Q39 1 0.8058 0.7159 0.3508 11.00000 0.05 0.18 Q40 1 1.0046 0.4963 0.1278 11.00000 0.05 0.16 Q41 1 0.9746 0.8765 0.0945 11.00000 0.05 0.16 Q42 1 0.1195 0.3665 0.0827 11.00000 0.05 0.15 Q43 1 0.1716 0.9972 0.0254 11.00000 0.05 0.15 Q44 1 0.1818 0.3408 0.0800 11.00000 0.05 0.14 Q45 1 0.2077 1.0350 0.0810 11.00000 0.05 0.14 Q46 1 0.6961 0.7313 0.3623 11.00000 0.05 0.14 Q47 1 0.2687 1.0581 0.0713 11.00000 0.05 0.13 Q48 1 0.4649 0.7153 0.2369 11.00000 0.05 0.13 Q49 1 0.7142 0.4975 0.1100 11.00000 0.05 0.12 Q50 1 0.0396 0.2643 0.1346 11.00000 0.05 0.12 Q51 1 0.1538 0.9741 0.1194 11.00000 0.05 0.12 Q52 1 0.6624 0.7562 0.0992 11.00000 0.05 0.12 Q53 1 0.3268 1.1201 0.1304 11.00000 0.05 0.12 Q54 1 0.6817 0.5935 0.3820 11.00000 0.05 0.12 Q55 1 0.9220 0.9007 0.1494 11.00000 0.05 0.12 Q56 1 0.2032 0.9256 0.1414 11.00000 0.05 0.12 ; _shelx_res_checksum 64253 ####################################################################### # # 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_I _database_code_depnum_ccdc_archive 'CCDC 1427668' _audit_update_record ; 2015-09-25 deposited with the CCDC. 2016-03-15 downloaded from the CCDC. ; # start Validation Reply Form _vrf_PLAT094_I ; PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.10 Report RESPONSE: a small amount of negative difference density at both Phosphorus atoms ; # Added during the CSD deposition process: Friday 25th of September 2015 01:59:27 PM # end Validation Reply Form _chemical_name_systematic ? _chemical_name_common YR6 _chemical_formula_moiety ? _chemical_formula_sum 'C54 H36 N6 O6 P2' _chemical_formula_iupac ? _chemical_formula_weight 926.83 _chemical_melting_point ? _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2381(6) _cell_length_b 13.0126(8) _cell_length_c 17.4162(11) _cell_angle_alpha 89.311(2) _cell_angle_beta 88.175(2) _cell_angle_gamma 67.8250(10) _cell_volume 2147.6(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9874 _cell_measurement_theta_min 2.1758 _cell_measurement_theta_max 34.3208 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'elongated prism' _exptl_crystal_colour 'translucent intense red-green' _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.98 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'fine-focus tube' _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'TRIUMPH curved-crystal' _diffrn_measurement_device_type 'BRUKER APEX II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 120588 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 33.73 _diffrn_reflns_theta_full 33.73 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 17096 _reflns_number_gt 14842 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_gt 0.0979 _refine_ls_wR_factor_ref 0.1036 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_number_reflns 17096 _refine_ls_number_parameters 615 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.6492P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.610 _refine_diff_density_min -0.291 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.30C (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.30C (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? 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 P P1 0.21376(2) 0.076034(16) 0.609095(11) 0.01053(4) Uani d . . . 1 . . O O1 0.33764(6) 0.08295(5) 0.56828(4) 0.01535(11) Uani d . . . 1 . . N N1 0.07546(7) 0.19892(5) 0.60842(4) 0.01218(11) Uani d . . . 1 . . C C1 0.09345(8) 0.30061(6) 0.59631(5) 0.01302(12) Uani d . . . 1 . . P P2 0.28024(2) 0.282684(17) 0.105549(12) 0.01340(4) Uani d . . . 1 . . O O2 -0.31645(7) 0.26467(6) 0.74490(4) 0.02028(12) Uani d . . . 1 . . N N2 -0.29602(7) 0.09029(6) 0.70732(4) 0.01587(12) Uani d . . . 1 . . C C2 0.18917(9) 0.32493(7) 0.54790(5) 0.01615(14) Uani d . . . 1 . . H H2 0.2583 0.2691 0.5177 0.019 Uiso calc . . R 1 . . N N3 0.15427(7) -0.01414(5) 0.56829(4) 0.01158(11) Uani d . . . 1 . . O O3 -0.21792(7) -0.08060(6) 0.65009(4) 0.02029(12) Uani d . . . 1 . . C C3 0.17873(10) 0.43458(7) 0.54587(6) 0.02037(16) Uani d . . . 1 . . H H3 0.2428 0.4538 0.5137 0.024 Uiso calc . . R 1 . . O O4 0.40559(7) 0.21666(6) 0.05936(4) 0.02052(13) Uani d . . . 1 . . N N4 0.18966(8) 0.40531(6) 0.06324(4) 0.01519(12) Uani d . . . 1 . . C C4 0.07638(10) 0.51782(7) 0.58989(6) 0.02093(16) Uani d . . . 1 . . H H4 0.0737 0.5916 0.5878 0.025 Uiso calc . . R 1 . . O O5 -0.17845(8) 0.66351(6) 0.17449(5) 0.02764(16) Uani d . . . 1 . . N N5 -0.22111(8) 0.52089(7) 0.23376(5) 0.02032(14) Uani d . . . 1 . . C C5 -0.02072(10) 0.49379(7) 0.63626(5) 0.01848(15) Uani d . . . 1 . . H H5 -0.091 0.5504 0.6653 0.022 Uiso calc . . R 1 . . N N6 0.16528(7) 0.21881(6) 0.11567(4) 0.01406(12) Uani d . . . 1 . . C C35 0.06378(10) 0.59162(7) 0.06864(6) 0.02020(16) Uani d . . . 1 . . H H35 -0.0061 0.6619 0.0819 0.024 Uiso calc . . R 1 . . C C6 -0.01275(9) 0.38354(7) 0.63924(5) 0.01465(13) Uani d . . . 1 . . O O6 -0.20706(8) 0.34711(7) 0.27126(5) 0.02598(15) Uani d . . . 1 . . C C17 0.25058(10) -0.29106(7) 0.49305(5) 0.01828(15) Uani d . . . 1 . . H H17 0.21 -0.3457 0.4944 0.022 Uiso calc . . R 1 . . C C18 0.37754(10) -0.31048(7) 0.45436(5) 0.01927(15) Uani d . . . 1 . . H H18 0.425 -0.3794 0.429 0.023 Uiso calc . . R 1 . . C C7 -0.09903(9) 0.33279(7) 0.67674(5) 0.01561(14) Uani d . . . 1 . . H H7 -0.1784 0.3688 0.7099 0.019 Uiso calc . . R 1 . . C C8 -0.04706(8) 0.22257(6) 0.65648(5) 0.01312(13) Uani d . . . 1 . . C C9 -0.11140(8) 0.14311(6) 0.66893(5) 0.01288(12) Uani d . . . 1 . . C C10 -0.25152(8) 0.17769(7) 0.71218(5) 0.01496(13) Uani d . . . 1 . . C C11 -0.43122(9) 0.09134(8) 0.73607(6) 0.02139(17) Uani d . . . 1 . . H H11A -0.4862 0.0837 0.693 0.032 Uiso calc . . R 1 . . H H11B -0.4829 0.1616 0.7628 0.032 Uiso calc . . R 1 . . H H11C -0.4158 0.0294 0.7719 0.032 Uiso calc . . R 1 . . C C14 0.03668(8) -0.03782(6) 0.59649(4) 0.01221(12) Uani d . . . 1 . . C C13 -0.07899(8) 0.03769(6) 0.64153(5) 0.01254(12) Uani d . . . 1 . . C C12 -0.20040(8) 0.00392(7) 0.66501(5) 0.01458(13) Uani d . . . 1 . . C C26 0.32415(10) -0.11661(8) 0.79858(5) 0.01935(15) Uani d . . . 1 . . H H26 0.3571 -0.1935 0.8106 0.023 Uiso calc . . R 1 . . C C15 0.05300(9) -0.14281(7) 0.57291(5) 0.01516(13) Uani d . . . 1 . . H H15 -0.0114 -0.1784 0.5833 0.018 Uiso calc . . R 1 . . C C16 0.18291(9) -0.18875(7) 0.53032(5) 0.01424(13) Uani d . . . 1 . . C C30 0.37297(10) 0.41054(8) -0.03775(5) 0.02107(16) Uani d . . . 1 . . H H30 0.4225 0.3325 -0.0411 0.025 Uiso calc . . R 1 . . C C28 0.23904(8) 0.03223(6) 0.70672(4) 0.01191(12) Uani d . . . 1 . . C C19 0.43747(9) -0.22927(7) 0.45207(5) 0.01719(14) Uani d . . . 1 . . H H19 0.5246 -0.2447 0.4248 0.021 Uiso calc . . R 1 . . C C29 0.25603(9) 0.45702(7) 0.01183(5) 0.01701(14) Uani d . . . 1 . . C C34 0.17915(10) 0.57249(7) 0.01560(5) 0.02000(16) Uani d . . . 1 . . C C38 -0.14634(9) 0.56483(7) 0.18576(6) 0.01910(16) Uani d . . . 1 . . C C36 0.07099(9) 0.49051(7) 0.09736(5) 0.01596(14) Uani d . . . 1 . . C C20 0.37321(8) -0.12726(7) 0.48843(5) 0.01448(13) Uani d . . . 1 . . H H20 0.4143 -0.0729 0.4867 0.017 Uiso calc . . R 1 . . C C37 -0.02467(9) 0.46906(7) 0.15135(5) 0.01518(13) Uani d . . . 1 . . C C21 0.24510(8) -0.10864(6) 0.52775(4) 0.01203(12) Uani d . . . 1 . . C C39 -0.34475(10) 0.58747(10) 0.27930(7) 0.0292(2) Uani d . . . 1 . . H H39A -0.4263 0.6169 0.2462 0.044 Uiso calc . . R 1 . . H H39B -0.3278 0.6492 0.3028 0.044 Uiso calc . . R 1 . . H H39C -0.3637 0.5413 0.3196 0.044 Uiso calc . . R 1 . . C C40 -0.16262(9) 0.40608(8) 0.23347(5) 0.01827(15) Uani d . . . 1 . . C C41 -0.03647(8) 0.37358(7) 0.17858(5) 0.01423(13) Uani d . . . 1 . . C C31 0.41397(12) 0.48331(10) -0.08206(6) 0.0261(2) Uani d . . . 1 . . H H31 0.4936 0.4542 -0.1162 0.031 Uiso calc . . R 1 . . C C42 0.03809(8) 0.25876(6) 0.16048(5) 0.01359(13) Uani d . . . 1 . . C C25 0.31430(10) -0.03997(9) 0.85557(5) 0.02235(17) Uani d . . . 1 . . H H25 0.3408 -0.0647 0.9064 0.027 Uiso calc . . R 1 . . C C24 0.26586(10) 0.07286(8) 0.83866(5) 0.02120(16) Uani d . . . 1 . . H H24 0.2584 0.125 0.8779 0.025 Uiso calc . . R 1 . . C C23 0.22844(9) 0.10914(7) 0.76420(5) 0.01599(14) Uani d . . . 1 . . H H23 0.1957 0.1861 0.7524 0.019 Uiso calc . . R 1 . . C C27 0.28589(9) -0.08117(7) 0.72401(5) 0.01496(13) Uani d . . . 1 . . H H27 0.2915 -0.1334 0.6851 0.018 Uiso calc . . R 1 . . C C54 0.37103(10) 0.25672(8) 0.33152(5) 0.02031(16) Uani d . . . 1 . . H H54 0.3739 0.2076 0.3728 0.024 Uiso calc . . R 1 . . C C55 0.32033(9) 0.24234(7) 0.26087(5) 0.01620(14) Uani d . . . 1 . . H H55 0.289 0.1831 0.2539 0.019 Uiso calc . . R 1 . . C C53 0.41740(10) 0.34304(9) 0.34145(6) 0.02356(17) Uani d . . . 1 . . H H53 0.4548 0.3515 0.3891 0.028 Uiso calc . . R 1 . . C C52 0.40930(11) 0.41744(9) 0.28172(6) 0.02395(18) Uani d . . . 1 . . H H52 0.4388 0.4775 0.2893 0.029 Uiso calc . . R 1 . . C C51 0.35808(9) 0.40389(8) 0.21107(6) 0.01927(15) Uani d . . . 1 . . H H51 0.3521 0.4547 0.1705 0.023 Uiso calc . . R 1 . . C C50 0.31539(8) 0.31488(7) 0.20019(5) 0.01407(13) Uani d . . . 1 . . C C49 0.20042(9) 0.10386(7) 0.10439(5) 0.01537(14) Uani d . . . 1 . . C C48 0.31524(11) 0.02511(7) 0.06543(5) 0.02244(17) Uani d . . . 1 . . H H48 0.3872 0.0445 0.0412 0.027 Uiso calc . . R 1 . . C C47 0.31956(13) -0.08295(8) 0.06363(6) 0.0273(2) Uani d . . . 1 . . H H47 0.397 -0.1386 0.0381 0.033 Uiso calc . . R 1 . . C C46 0.21280(14) -0.11224(8) 0.09842(6) 0.0274(2) Uani d . . . 1 . . H H46 0.2189 -0.1868 0.0956 0.033 Uiso calc . . R 1 . . C C45 0.09932(12) -0.03420(8) 0.13661(6) 0.02298(17) Uani d . . . 1 . . H H45 0.0267 -0.0539 0.1597 0.028 Uiso calc . . R 1 . . C C33 0.22343(12) 0.64410(9) -0.03016(6) 0.0261(2) Uani d . . . 1 . . H H33 0.1732 0.7221 -0.0282 0.031 Uiso calc . . R 1 . . C C44 0.09370(10) 0.07529(7) 0.14063(5) 0.01656(14) Uani d . . . 1 . . C C43 -0.00544(9) 0.17278(7) 0.17606(5) 0.01668(14) Uani d . . . 1 . . H H43 -0.0874 0.1775 0.2054 0.02 Uiso calc . . R 1 . . C C32 0.34095(13) 0.59860(10) -0.07780(6) 0.0289(2) Uani d . . . 1 . . H H32 0.373 0.646 -0.1082 0.035 Uiso calc . . R 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 P1 0.00845(8) 0.01081(8) 0.01276(8) -0.00417(6) 0.00025(6) 0.00040(6) O1 0.0118(2) 0.0163(2) 0.0194(3) -0.0072(2) 0.0035(2) -0.0007(2) N1 0.0102(3) 0.0107(2) 0.0155(3) -0.0038(2) 0.0000(2) 0.0015(2) C1 0.0128(3) 0.0118(3) 0.0149(3) -0.0051(2) -0.0027(2) 0.0025(2) P2 0.01100(8) 0.01314(8) 0.01450(9) -0.00300(7) 0.00124(6) 0.00283(7) O2 0.0135(3) 0.0189(3) 0.0247(3) -0.0021(2) 0.0041(2) -0.0002(2) N2 0.0099(3) 0.0186(3) 0.0193(3) -0.0058(2) 0.0017(2) 0.0029(2) C2 0.0167(3) 0.0149(3) 0.0178(3) -0.0072(3) -0.0004(3) 0.0034(3) N3 0.0099(3) 0.0124(3) 0.0131(3) -0.0049(2) 0.0007(2) -0.0007(2) O3 0.0182(3) 0.0199(3) 0.0263(3) -0.0116(2) 0.0024(2) 0.0023(2) C3 0.0224(4) 0.0162(3) 0.0246(4) -0.0097(3) -0.0014(3) 0.0058(3) O4 0.0153(3) 0.0214(3) 0.0195(3) -0.0014(2) 0.0061(2) 0.0034(2) N4 0.0140(3) 0.0138(3) 0.0173(3) -0.0047(2) -0.0016(2) 0.0044(2) C4 0.0232(4) 0.0139(3) 0.0269(4) -0.0083(3) -0.0034(3) 0.0037(3) O5 0.0258(3) 0.0135(3) 0.0396(4) -0.0023(2) -0.0049(3) -0.0071(3) N5 0.0126(3) 0.0191(3) 0.0251(4) -0.0011(2) 0.0002(3) -0.0084(3) C5 0.0191(4) 0.0122(3) 0.0233(4) -0.0047(3) -0.0031(3) 0.0008(3) N6 0.0139(3) 0.0110(3) 0.0165(3) -0.0040(2) 0.0022(2) -0.0012(2) C35 0.0235(4) 0.0131(3) 0.0248(4) -0.0075(3) -0.0079(3) 0.0034(3) C6 0.0134(3) 0.0121(3) 0.0178(3) -0.0039(2) -0.0022(3) 0.0011(3) O6 0.0196(3) 0.0297(4) 0.0288(4) -0.0101(3) 0.0078(3) -0.0040(3) C17 0.0216(4) 0.0141(3) 0.0198(4) -0.0075(3) 0.0013(3) -0.0020(3) C18 0.0208(4) 0.0156(3) 0.0192(4) -0.0044(3) 0.0014(3) -0.0034(3) C7 0.0125(3) 0.0136(3) 0.0195(3) -0.0036(3) 0.0005(3) -0.0006(3) C8 0.0098(3) 0.0131(3) 0.0160(3) -0.0038(2) -0.0003(2) 0.0011(2) C9 0.0091(3) 0.0138(3) 0.0152(3) -0.0038(2) 0.0000(2) 0.0018(2) C10 0.0096(3) 0.0169(3) 0.0169(3) -0.0035(3) -0.0002(2) 0.0036(3) C11 0.0121(3) 0.0259(4) 0.0266(4) -0.0081(3) 0.0042(3) 0.0052(3) C14 0.0102(3) 0.0137(3) 0.0138(3) -0.0058(2) 0.0000(2) 0.0013(2) C13 0.0096(3) 0.0142(3) 0.0143(3) -0.0051(2) -0.0005(2) 0.0024(2) C12 0.0110(3) 0.0173(3) 0.0160(3) -0.0061(3) -0.0009(2) 0.0047(3) C26 0.0171(4) 0.0180(3) 0.0199(4) -0.0033(3) -0.0027(3) 0.0061(3) C15 0.0155(3) 0.0145(3) 0.0176(3) -0.0080(3) 0.0007(3) 0.0002(3) C16 0.0154(3) 0.0131(3) 0.0150(3) -0.0064(3) 0.0000(3) 0.0000(2) C30 0.0214(4) 0.0274(4) 0.0180(4) -0.0133(3) -0.0027(3) 0.0078(3) C28 0.0094(3) 0.0120(3) 0.0141(3) -0.0036(2) -0.0010(2) 0.0006(2) C19 0.0152(3) 0.0188(3) 0.0156(3) -0.0042(3) 0.0013(3) -0.0028(3) C29 0.0190(4) 0.0192(3) 0.0162(3) -0.0109(3) -0.0054(3) 0.0064(3) C34 0.0253(4) 0.0180(4) 0.0213(4) -0.0128(3) -0.0105(3) 0.0074(3) C38 0.0148(3) 0.0147(3) 0.0252(4) -0.0020(3) -0.0048(3) -0.0068(3) C36 0.0152(3) 0.0125(3) 0.0200(4) -0.0047(3) -0.0041(3) 0.0010(3) C20 0.0128(3) 0.0168(3) 0.0137(3) -0.0055(3) 0.0007(2) -0.0013(3) C37 0.0126(3) 0.0124(3) 0.0195(3) -0.0032(2) -0.0028(3) -0.0022(3) C21 0.0116(3) 0.0125(3) 0.0119(3) -0.0044(2) -0.0005(2) -0.0001(2) C39 0.0147(4) 0.0309(5) 0.0352(5) -0.0007(3) 0.0028(4) -0.0164(4) C40 0.0114(3) 0.0209(4) 0.0208(4) -0.0041(3) 0.0003(3) -0.0054(3) C41 0.0108(3) 0.0134(3) 0.0175(3) -0.0033(2) -0.0004(2) -0.0024(3) C31 0.0289(5) 0.0384(5) 0.0197(4) -0.0223(4) -0.0060(3) 0.0116(4) C42 0.0115(3) 0.0127(3) 0.0162(3) -0.0041(2) 0.0003(2) -0.0010(2) C25 0.0201(4) 0.0273(4) 0.0156(4) -0.0043(3) -0.0032(3) 0.0043(3) C24 0.0210(4) 0.0246(4) 0.0156(3) -0.0056(3) -0.0026(3) -0.0029(3) C23 0.0158(3) 0.0152(3) 0.0164(3) -0.0050(3) -0.0018(3) -0.0014(3) C27 0.0131(3) 0.0125(3) 0.0177(3) -0.0030(2) -0.0015(3) 0.0015(3) C54 0.0184(4) 0.0241(4) 0.0165(3) -0.0059(3) -0.0007(3) 0.0027(3) C55 0.0152(3) 0.0166(3) 0.0167(3) -0.0060(3) 0.0004(3) 0.0033(3) C53 0.0199(4) 0.0295(4) 0.0215(4) -0.0091(3) -0.0031(3) -0.0027(3) C52 0.0209(4) 0.0255(4) 0.0295(5) -0.0131(3) -0.0030(3) -0.0018(4) C51 0.0165(4) 0.0193(4) 0.0246(4) -0.0096(3) -0.0013(3) 0.0035(3) C50 0.0104(3) 0.0147(3) 0.0167(3) -0.0044(2) 0.0001(2) 0.0027(3) C49 0.0203(4) 0.0112(3) 0.0129(3) -0.0039(3) 0.0000(3) -0.0005(2) C48 0.0294(5) 0.0143(3) 0.0169(4) -0.0012(3) 0.0054(3) -0.0012(3) C47 0.0434(6) 0.0136(3) 0.0169(4) -0.0018(4) 0.0030(4) -0.0027(3) C46 0.0493(6) 0.0129(3) 0.0187(4) -0.0098(4) -0.0046(4) -0.0007(3) C45 0.0356(5) 0.0157(3) 0.0212(4) -0.0135(3) -0.0055(4) 0.0016(3) C33 0.0368(5) 0.0243(4) 0.0262(4) -0.0209(4) -0.0149(4) 0.0121(4) C44 0.0217(4) 0.0131(3) 0.0160(3) -0.0076(3) -0.0031(3) 0.0008(3) C43 0.0158(3) 0.0155(3) 0.0200(4) -0.0074(3) -0.0004(3) 0.0010(3) C32 0.0388(6) 0.0364(5) 0.0241(4) -0.0281(5) -0.0124(4) 0.0153(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.4661(6) ? P1 N3 . 1.6852(7) ? P1 N1 . 1.6892(7) ? P1 C28 . 1.7821(8) ? N1 C1 . 1.4156(10) ? N1 C8 . 1.4202(10) ? C1 C2 . 1.3951(11) ? C1 C6 . 1.4098(11) ? P2 O4 . 1.4666(7) ? P2 N6 . 1.6819(7) ? P2 N4 . 1.6874(7) ? P2 C50 . 1.7861(9) ? O2 C10 . 1.2128(11) ? N2 C10 . 1.3799(11) ? N2 C12 . 1.3813(11) ? N2 C11 . 1.4521(11) ? C2 C3 . 1.3901(12) ? C2 H2 . 0.95 ? N3 C21 . 1.4111(10) ? N3 C14 . 1.4228(10) ? O3 C12 . 1.2116(11) ? C3 C4 . 1.4039(14) ? C3 H3 . 0.95 ? N4 C29 . 1.4172(11) ? N4 C36 . 1.4182(11) ? C4 C5 . 1.3840(13) ? C4 H4 . 0.95 ? O5 C38 . 1.2144(11) ? N5 C38 . 1.3747(13) ? N5 C40 . 1.3840(12) ? N5 C39 . 1.4514(12) ? C5 C6 . 1.4063(11) ? C5 H5 . 0.95 ? N6 C49 . 1.4148(10) ? N6 C42 . 1.4173(10) ? C35 C36 . 1.3784(12) ? C35 C34 . 1.4228(14) ? C35 H35 . 0.95 ? C6 C7 . 1.4268(12) ? O6 C40 . 1.2089(12) ? C17 C18 . 1.3812(13) ? C17 C16 . 1.4035(12) ? C17 H17 . 0.95 ? C18 C19 . 1.4077(13) ? C18 H18 . 0.95 ? C7 C8 . 1.3743(11) ? C7 H7 . 0.95 ? C8 C9 . 1.4318(11) ? C9 C13 . 1.3717(11) ? C9 C10 . 1.5099(11) ? C11 H11A . 0.98 ? C11 H11B . 0.98 ? C11 H11C . 0.98 ? C14 C15 . 1.3783(11) ? C14 C13 . 1.4368(11) ? C13 C12 . 1.5104(11) ? C26 C25 . 1.3898(14) ? C26 C27 . 1.3908(12) ? C26 H26 . 0.95 ? C15 C16 . 1.4227(12) ? C15 H15 . 0.95 ? C16 C21 . 1.4115(11) ? C30 C31 . 1.3894(13) ? C30 C29 . 1.3946(13) ? C30 H30 . 0.95 ? C28 C23 . 1.3967(11) ? C28 C27 . 1.4009(11) ? C19 C20 . 1.3893(12) ? C19 H19 . 0.95 ? C29 C34 . 1.4099(13) ? C34 C33 . 1.4096(13) ? C38 C37 . 1.5041(12) ? C36 C37 . 1.4362(12) ? C20 C21 . 1.3982(11) ? C20 H20 . 0.95 ? C37 C41 . 1.3707(11) ? C39 H39A . 0.98 ? C39 H39B . 0.98 ? C39 H39C . 0.98 ? C40 C41 . 1.5097(12) ? C41 C42 . 1.4316(11) ? C31 C32 . 1.4028(17) ? C31 H31 . 0.95 ? C42 C43 . 1.3731(11) ? C25 C24 . 1.3920(14) ? C25 H25 . 0.95 ? C24 C23 . 1.3900(12) ? C24 H24 . 0.95 ? C23 H23 . 0.95 ? C27 H27 . 0.95 ? C54 C53 . 1.3890(14) ? C54 C55 . 1.3922(13) ? C54 H54 . 0.95 ? C55 C50 . 1.3977(11) ? C55 H55 . 0.95 ? C53 C52 . 1.3954(15) ? C53 H53 . 0.95 ? C52 C51 . 1.3915(14) ? C52 H52 . 0.95 ? C51 C50 . 1.4005(12) ? C51 H51 . 0.95 ? C49 C48 . 1.3960(12) ? C49 C44 . 1.4099(12) ? C48 C47 . 1.3908(14) ? C48 H48 . 0.95 ? C47 C46 . 1.4050(17) ? C47 H47 . 0.95 ? C46 C45 . 1.3783(15) ? C46 H46 . 0.95 ? C45 C44 . 1.4065(12) ? C45 H45 . 0.95 ? C33 C32 . 1.3773(18) ? C33 H33 . 0.95 ? C44 C43 . 1.4238(12) ? C43 H43 . 0.95 ? C32 H32 . 0.95 ? 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 P1 N3 . . 112.89(4) ? O1 P1 N1 . . 111.51(4) ? N3 P1 N1 . . 104.80(3) ? O1 P1 C28 . . 115.53(4) ? N3 P1 C28 . . 104.24(3) ? N1 P1 C28 . . 107.02(4) ? C1 N1 C8 . . 106.75(6) ? C1 N1 P1 . . 121.99(5) ? C8 N1 P1 . . 123.25(5) ? C2 C1 C6 . . 121.95(7) ? C2 C1 N1 . . 129.74(7) ? C6 C1 N1 . . 108.18(7) ? O4 P2 N6 . . 111.79(4) ? O4 P2 N4 . . 111.55(4) ? N6 P2 N4 . . 105.31(4) ? O4 P2 C50 . . 114.85(4) ? N6 P2 C50 . . 106.55(4) ? N4 P2 C50 . . 106.16(4) ? C10 N2 C12 . . 111.13(7) ? C10 N2 C11 . . 125.17(8) ? C12 N2 C11 . . 123.46(8) ? C3 C2 C1 . . 116.94(8) ? C3 C2 H2 . . 121.5 ? C1 C2 H2 . . 121.5 ? C21 N3 C14 . . 107.38(6) ? C21 N3 P1 . . 122.06(5) ? C14 N3 P1 . . 124.65(6) ? C2 C3 C4 . . 121.98(8) ? C2 C3 H3 . . 119.0 ? C4 C3 H3 . . 119.0 ? C29 N4 C36 . . 107.23(7) ? C29 N4 P2 . . 121.92(6) ? C36 N4 P2 . . 124.36(6) ? C5 C4 C3 . . 120.83(8) ? C5 C4 H4 . . 119.6 ? C3 C4 H4 . . 119.6 ? C38 N5 C40 . . 111.43(7) ? C38 N5 C39 . . 123.79(9) ? C40 N5 C39 . . 124.78(9) ? C4 C5 C6 . . 118.36(8) ? C4 C5 H5 . . 120.8 ? C6 C5 H5 . . 120.8 ? C49 N6 C42 . . 107.17(7) ? C49 N6 P2 . . 124.41(6) ? C42 N6 P2 . . 125.15(6) ? C36 C35 C34 . . 108.15(8) ? C36 C35 H35 . . 125.9 ? C34 C35 H35 . . 125.9 ? C5 C6 C1 . . 119.89(8) ? C5 C6 C7 . . 132.51(8) ? C1 C6 C7 . . 107.54(7) ? C18 C17 C16 . . 118.55(8) ? C18 C17 H17 . . 120.7 ? C16 C17 H17 . . 120.7 ? C17 C18 C19 . . 120.75(8) ? C17 C18 H18 . . 119.6 ? C19 C18 H18 . . 119.6 ? C8 C7 C6 . . 107.97(7) ? C8 C7 H7 . . 126.0 ? C6 C7 H7 . . 126.0 ? C7 C8 N1 . . 109.47(7) ? C7 C8 C9 . . 128.20(7) ? N1 C8 C9 . . 121.65(7) ? C13 C9 C8 . . 132.33(7) ? C13 C9 C10 . . 107.97(7) ? C8 C9 C10 . . 119.27(7) ? O2 C10 N2 . . 124.89(8) ? O2 C10 C9 . . 128.42(8) ? N2 C10 C9 . . 106.69(7) ? N2 C11 H11A . . 109.5 ? N2 C11 H11B . . 109.5 ? H11A C11 H11B . . 109.5 ? N2 C11 H11C . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 109.5 ? C15 C14 N3 . . 108.78(7) ? C15 C14 C13 . . 126.86(7) ? N3 C14 C13 . . 124.36(7) ? C9 C13 C14 . . 134.09(7) ? C9 C13 C12 . . 106.91(7) ? C14 C13 C12 . . 118.96(7) ? O3 C12 N2 . . 123.80(8) ? O3 C12 C13 . . 128.92(8) ? N2 C12 C13 . . 107.26(7) ? C25 C26 C27 . . 120.22(8) ? C25 C26 H26 . . 119.9 ? C27 C26 H26 . . 119.9 ? C14 C15 C16 . . 108.24(7) ? C14 C15 H15 . . 125.9 ? C16 C15 H15 . . 125.9 ? C17 C16 C21 . . 119.86(8) ? C17 C16 C15 . . 132.42(8) ? C21 C16 C15 . . 107.70(7) ? C31 C30 C29 . . 117.11(10) ? C31 C30 H30 . . 121.4 ? C29 C30 H30 . . 121.4 ? C23 C28 C27 . . 120.25(7) ? C23 C28 P1 . . 119.90(6) ? C27 C28 P1 . . 119.42(6) ? C20 C19 C18 . . 122.10(8) ? C20 C19 H19 . . 118.9 ? C18 C19 H19 . . 118.9 ? C30 C29 C34 . . 121.98(8) ? C30 C29 N4 . . 130.19(8) ? C34 C29 N4 . . 107.81(8) ? C33 C34 C29 . . 119.49(10) ? C33 C34 C35 . . 132.74(9) ? C29 C34 C35 . . 107.76(8) ? O5 C38 N5 . . 124.11(9) ? O5 C38 C37 . . 128.68(9) ? N5 C38 C37 . . 107.20(7) ? C35 C36 N4 . . 109.04(8) ? C35 C36 C37 . . 127.82(8) ? N4 C36 C37 . . 123.12(7) ? C19 C20 C21 . . 116.70(8) ? C19 C20 H20 . . 121.6 ? C21 C20 H20 . . 121.6 ? C41 C37 C36 . . 133.26(8) ? C41 C37 C38 . . 107.19(8) ? C36 C37 C38 . . 119.46(7) ? C20 C21 N3 . . 130.06(7) ? C20 C21 C16 . . 122.03(7) ? N3 C21 C16 . . 107.88(7) ? N5 C39 H39A . . 109.5 ? N5 C39 H39B . . 109.5 ? H39A C39 H39B . . 109.5 ? N5 C39 H39C . . 109.5 ? H39A C39 H39C . . 109.5 ? H39B C39 H39C . . 109.5 ? O6 C40 N5 . . 124.79(8) ? O6 C40 C41 . . 128.95(8) ? N5 C40 C41 . . 106.26(8) ? C37 C41 C42 . . 132.82(8) ? C37 C41 C40 . . 107.87(7) ? C42 C41 C40 . . 119.12(7) ? C30 C31 C32 . . 121.77(10) ? C30 C31 H31 . . 119.1 ? C32 C31 H31 . . 119.1 ? C43 C42 N6 . . 109.25(7) ? C43 C42 C41 . . 127.08(8) ? N6 C42 C41 . . 123.39(7) ? C26 C25 C24 . . 120.39(8) ? C26 C25 H25 . . 119.8 ? C24 C25 H25 . . 119.8 ? C23 C24 C25 . . 119.88(8) ? C23 C24 H24 . . 120.1 ? C25 C24 H24 . . 120.1 ? C24 C23 C28 . . 119.84(8) ? C24 C23 H23 . . 120.1 ? C28 C23 H23 . . 120.1 ? C26 C27 C28 . . 119.41(8) ? C26 C27 H27 . . 120.3 ? C28 C27 H27 . . 120.3 ? C53 C54 C55 . . 119.82(9) ? C53 C54 H54 . . 120.1 ? C55 C54 H54 . . 120.1 ? C54 C55 C50 . . 120.12(8) ? C54 C55 H55 . . 119.9 ? C50 C55 H55 . . 119.9 ? C54 C53 C52 . . 120.31(9) ? C54 C53 H53 . . 119.8 ? C52 C53 H53 . . 119.8 ? C51 C52 C53 . . 120.15(9) ? C51 C52 H52 . . 119.9 ? C53 C52 H52 . . 119.9 ? C52 C51 C50 . . 119.61(8) ? C52 C51 H51 . . 120.2 ? C50 C51 H51 . . 120.2 ? C55 C50 C51 . . 119.94(8) ? C55 C50 P2 . . 119.94(6) ? C51 C50 P2 . . 119.46(6) ? C48 C49 C44 . . 121.61(8) ? C48 C49 N6 . . 130.62(8) ? C44 C49 N6 . . 107.77(7) ? C47 C48 C49 . . 117.05(9) ? C47 C48 H48 . . 121.5 ? C49 C48 H48 . . 121.5 ? C48 C47 C46 . . 121.96(9) ? C48 C47 H47 . . 119.0 ? C46 C47 H47 . . 119.0 ? C45 C46 C47 . . 120.84(9) ? C45 C46 H46 . . 119.6 ? C47 C46 H46 . . 119.6 ? C46 C45 C44 . . 118.39(10) ? C46 C45 H45 . . 120.8 ? C44 C45 H45 . . 120.8 ? C32 C33 C34 . . 118.65(10) ? C32 C33 H33 . . 120.7 ? C34 C33 H33 . . 120.7 ? C45 C44 C49 . . 120.13(8) ? C45 C44 C43 . . 132.15(9) ? C49 C44 C43 . . 107.72(7) ? C42 C43 C44 . . 108.06(8) ? C42 C43 H43 . . 126.0 ? C44 C43 H43 . . 126.0 ? C33 C32 C31 . . 120.96(9) ? C33 C32 H32 . . 119.5 ? C31 C32 H32 . . 119.5 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 P1 N1 C1 . . . . -21.72(8) ? N3 P1 N1 C1 . . . . -144.18(6) ? C28 P1 N1 C1 . . . . 105.52(7) ? O1 P1 N1 C8 . . . . -166.42(6) ? N3 P1 N1 C8 . . . . 71.13(7) ? C28 P1 N1 C8 . . . . -39.17(7) ? C8 N1 C1 C2 . . . . -173.23(8) ? P1 N1 C1 C2 . . . . 37.09(12) ? C8 N1 C1 C6 . . . . 2.63(8) ? P1 N1 C1 C6 . . . . -147.06(6) ? C6 C1 C2 C3 . . . . 2.32(12) ? N1 C1 C2 C3 . . . . 177.67(8) ? O1 P1 N3 C21 . . . . 29.86(7) ? N1 P1 N3 C21 . . . . 151.41(6) ? C28 P1 N3 C21 . . . . -96.29(6) ? O1 P1 N3 C14 . . . . 179.32(6) ? N1 P1 N3 C14 . . . . -59.13(7) ? C28 P1 N3 C14 . . . . 53.17(7) ? C1 C2 C3 C4 . . . . -0.41(13) ? O4 P2 N4 C29 . . . . -26.19(8) ? N6 P2 N4 C29 . . . . -147.65(7) ? C50 P2 N4 C29 . . . . 99.60(7) ? O4 P2 N4 C36 . . . . -174.27(7) ? N6 P2 N4 C36 . . . . 64.26(8) ? C50 P2 N4 C36 . . . . -48.49(8) ? C2 C3 C4 C5 . . . . -1.32(15) ? C3 C4 C5 C6 . . . . 1.12(14) ? O4 P2 N6 C49 . . . . 19.51(8) ? N4 P2 N6 C49 . . . . 140.81(7) ? C50 P2 N6 C49 . . . . -106.71(7) ? O4 P2 N6 C42 . . . . 176.42(6) ? N4 P2 N6 C42 . . . . -62.28(7) ? C50 P2 N6 C42 . . . . 50.20(7) ? C4 C5 C6 C1 . . . . 0.75(13) ? C4 C5 C6 C7 . . . . -175.92(9) ? C2 C1 C6 C5 . . . . -2.54(12) ? N1 C1 C6 C5 . . . . -178.78(7) ? C2 C1 C6 C7 . . . . 174.88(8) ? N1 C1 C6 C7 . . . . -1.36(9) ? C16 C17 C18 C19 . . . . -0.29(14) ? C5 C6 C7 C8 . . . . 176.48(9) ? C1 C6 C7 C8 . . . . -0.48(9) ? C6 C7 C8 N1 . . . . 2.15(9) ? C6 C7 C8 C9 . . . . -168.39(8) ? C1 N1 C8 C7 . . . . -2.98(9) ? P1 N1 C8 C7 . . . . 146.23(6) ? C1 N1 C8 C9 . . . . 168.30(7) ? P1 N1 C8 C9 . . . . -42.49(10) ? C7 C8 C9 C13 . . . . 168.81(9) ? N1 C8 C9 C13 . . . . -0.70(14) ? C7 C8 C9 C10 . . . . -2.70(13) ? N1 C8 C9 C10 . . . . -172.22(7) ? C12 N2 C10 O2 . . . . 178.76(8) ? C11 N2 C10 O2 . . . . 4.30(14) ? C12 N2 C10 C9 . . . . -0.62(9) ? C11 N2 C10 C9 . . . . -175.08(8) ? C13 C9 C10 O2 . . . . 179.99(9) ? C8 C9 C10 O2 . . . . -6.59(13) ? C13 C9 C10 N2 . . . . -0.66(9) ? C8 C9 C10 N2 . . . . 172.76(7) ? C21 N3 C14 C15 . . . . -1.08(9) ? P1 N3 C14 C15 . . . . -154.26(6) ? C21 N3 C14 C13 . . . . 179.37(7) ? P1 N3 C14 C13 . . . . 26.19(11) ? C8 C9 C13 C14 . . . . 6.99(16) ? C10 C9 C13 C14 . . . . 179.21(8) ? C8 C9 C13 C12 . . . . -170.68(8) ? C10 C9 C13 C12 . . . . 1.54(8) ? C15 C14 C13 C9 . . . . -179.49(9) ? N3 C14 C13 C9 . . . . -0.03(14) ? C15 C14 C13 C12 . . . . -2.03(12) ? N3 C14 C13 C12 . . . . 177.43(7) ? C10 N2 C12 O3 . . . . -177.18(8) ? C11 N2 C12 O3 . . . . -2.61(13) ? C10 N2 C12 C13 . . . . 1.55(9) ? C11 N2 C12 C13 . . . . 176.12(7) ? C9 C13 C12 O3 . . . . 176.71(9) ? C14 C13 C12 O3 . . . . -1.38(13) ? C9 C13 C12 N2 . . . . -1.93(9) ? C14 C13 C12 N2 . . . . 179.98(7) ? N3 C14 C15 C16 . . . . 1.04(9) ? C13 C14 C15 C16 . . . . -179.43(8) ? C18 C17 C16 C21 . . . . -0.09(13) ? C18 C17 C16 C15 . . . . 178.62(9) ? C14 C15 C16 C17 . . . . -179.43(9) ? C14 C15 C16 C21 . . . . -0.60(9) ? O1 P1 C28 C23 . . . . 83.13(7) ? N3 P1 C28 C23 . . . . -152.40(6) ? N1 P1 C28 C23 . . . . -41.71(7) ? O1 P1 C28 C27 . . . . -89.28(7) ? N3 P1 C28 C27 . . . . 35.19(7) ? N1 P1 C28 C27 . . . . 145.89(6) ? C17 C18 C19 C20 . . . . 0.36(14) ? C31 C30 C29 C34 . . . . 1.96(13) ? C31 C30 C29 N4 . . . . 179.77(9) ? C36 N4 C29 C30 . . . . -177.33(9) ? P2 N4 C29 C30 . . . . 29.86(13) ? C36 N4 C29 C34 . . . . 0.72(9) ? P2 N4 C29 C34 . . . . -152.10(6) ? C30 C29 C34 C33 . . . . -1.98(13) ? N4 C29 C34 C33 . . . . 179.78(8) ? C30 C29 C34 C35 . . . . 177.33(8) ? N4 C29 C34 C35 . . . . -0.92(10) ? C36 C35 C34 C33 . . . . 179.94(10) ? C36 C35 C34 C29 . . . . 0.77(10) ? C40 N5 C38 O5 . . . . 178.05(9) ? C39 N5 C38 O5 . . . . -2.56(15) ? C40 N5 C38 C37 . . . . -1.03(10) ? C39 N5 C38 C37 . . . . 178.36(8) ? C34 C35 C36 N4 . . . . -0.33(10) ? C34 C35 C36 C37 . . . . -178.68(8) ? C29 N4 C36 C35 . . . . -0.24(9) ? P2 N4 C36 C35 . . . . 151.74(7) ? C29 N4 C36 C37 . . . . 178.21(8) ? P2 N4 C36 C37 . . . . -29.81(12) ? C18 C19 C20 C21 . . . . -0.03(13) ? C35 C36 C37 C41 . . . . 172.96(9) ? N4 C36 C37 C41 . . . . -5.19(15) ? C35 C36 C37 C38 . . . . -2.98(13) ? N4 C36 C37 C38 . . . . 178.88(7) ? O5 C38 C37 C41 . . . . -176.96(9) ? N5 C38 C37 C41 . . . . 2.06(10) ? O5 C38 C37 C36 . . . . -0.06(14) ? N5 C38 C37 C36 . . . . 178.96(8) ? C19 C20 C21 N3 . . . . -178.49(8) ? C19 C20 C21 C16 . . . . -0.36(12) ? C14 N3 C21 C20 . . . . 179.04(8) ? P1 N3 C21 C20 . . . . -26.94(11) ? C14 N3 C21 C16 . . . . 0.70(8) ? P1 N3 C21 C16 . . . . 154.73(6) ? C17 C16 C21 C20 . . . . 0.43(12) ? C15 C16 C21 C20 . . . . -178.58(7) ? C17 C16 C21 N3 . . . . 178.93(7) ? C15 C16 C21 N3 . . . . -0.08(9) ? C38 N5 C40 O6 . . . . 179.17(9) ? C39 N5 C40 O6 . . . . -0.21(15) ? C38 N5 C40 C41 . . . . -0.29(10) ? C39 N5 C40 C41 . . . . -179.67(8) ? C36 C37 C41 C42 . . . . -3.76(17) ? C38 C37 C41 C42 . . . . 172.53(9) ? C36 C37 C41 C40 . . . . -178.50(9) ? C38 C37 C41 C40 . . . . -2.20(9) ? O6 C40 C41 C37 . . . . -177.81(10) ? N5 C40 C41 C37 . . . . 1.63(9) ? O6 C40 C41 C42 . . . . 6.61(14) ? N5 C40 C41 C42 . . . . -173.95(7) ? C29 C30 C31 C32 . . . . -0.38(14) ? C49 N6 C42 C43 . . . . -0.53(9) ? P2 N6 C42 C43 . . . . -160.74(6) ? C49 N6 C42 C41 . . . . -174.88(8) ? P2 N6 C42 C41 . . . . 24.91(11) ? C37 C41 C42 C43 . . . . -161.29(9) ? C40 C41 C42 C43 . . . . 12.98(13) ? C37 C41 C42 N6 . . . . 12.03(14) ? C40 C41 C42 N6 . . . . -173.71(7) ? C27 C26 C25 C24 . . . . 0.12(15) ? C26 C25 C24 C23 . . . . -0.65(15) ? C25 C24 C23 C28 . . . . 0.27(14) ? C27 C28 C23 C24 . . . . 0.64(12) ? P1 C28 C23 C24 . . . . -171.71(7) ? C25 C26 C27 C28 . . . . 0.78(13) ? C23 C28 C27 C26 . . . . -1.16(12) ? P1 C28 C27 C26 . . . . 171.22(7) ? C53 C54 C55 C50 . . . . -0.33(13) ? C55 C54 C53 C52 . . . . 2.01(15) ? C54 C53 C52 C51 . . . . -1.69(15) ? C53 C52 C51 C50 . . . . -0.30(15) ? C54 C55 C50 C51 . . . . -1.65(13) ? C54 C55 C50 P2 . . . . 168.99(7) ? C52 C51 C50 C55 . . . . 1.97(13) ? C52 C51 C50 P2 . . . . -168.72(7) ? O4 P2 C50 C55 . . . . -89.22(7) ? N6 P2 C50 C55 . . . . 35.14(8) ? N4 P2 C50 C55 . . . . 147.04(7) ? O4 P2 C50 C51 . . . . 81.47(8) ? N6 P2 C50 C51 . . . . -154.17(7) ? N4 P2 C50 C51 . . . . -42.28(8) ? C42 N6 C49 C48 . . . . -179.16(9) ? P2 N6 C49 C48 . . . . -18.77(13) ? C42 N6 C49 C44 . . . . 1.28(9) ? P2 N6 C49 C44 . . . . 161.66(6) ? C44 C49 C48 C47 . . . . 0.26(14) ? N6 C49 C48 C47 . . . . -179.26(9) ? C49 C48 C47 C46 . . . . 0.80(15) ? C48 C47 C46 C45 . . . . -0.61(16) ? C47 C46 C45 C44 . . . . -0.66(15) ? C29 C34 C33 C32 . . . . 0.34(14) ? C35 C34 C33 C32 . . . . -178.75(10) ? C46 C45 C44 C49 . . . . 1.68(14) ? C46 C45 C44 C43 . . . . -178.79(10) ? C48 C49 C44 C45 . . . . -1.51(13) ? N6 C49 C44 C45 . . . . 178.10(8) ? C48 C49 C44 C43 . . . . 178.86(8) ? N6 C49 C44 C43 . . . . -1.53(9) ? N6 C42 C43 C44 . . . . -0.42(10) ? C41 C42 C43 C44 . . . . 173.67(8) ? C45 C44 C43 C42 . . . . -178.36(9) ? C49 C44 C43 C42 . . . . 1.21(10) ? C34 C33 C32 C31 . . . . 1.20(15) ? C30 C31 C32 C33 . . . . -1.21(15) ?