# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Zhaohui Wang' _publ_contact_author_address ; Institue of Chemistry, Chinese Academy of Sciences Zhong Guan Cun Bei Yi Jie 2 Beijing 100080 CHINA ; _publ_contact_author_email WANGZHAOHUI@ICCAS.AC.CN _publ_section_title ; S-heterocyclic annelated perylene bisimide:synthesis and co-crystal with pyrene ; loop_ _publ_author_name 'Zhaohui Wang' 'Caiming Liu' 'Hualei Qian' # Attachment '5Ph.cif' data_60303b _database_code_depnum_ccdc_archive 'CCDC 612066' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H56 N2 O4 S2' _chemical_formula_weight 1005.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.317(3) _cell_length_b 11.425(4) _cell_length_c 15.518(5) _cell_angle_alpha 106.441(5) _cell_angle_beta 104.475(6) _cell_angle_gamma 94.316(6) _cell_volume 1352.3(8) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1247 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 26.36 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 530 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.711354 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 6745 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0946 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4727 _reflns_number_gt 2374 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.1453P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0056(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4727 _refine_ls_number_parameters 363 _refine_ls_number_restraints 234 _refine_ls_R_factor_all 0.1418 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.57128(14) 0.71997(8) -0.16389(7) 0.0538(4) Uani 1 1 d . . . N1 N 0.3709(4) 0.7277(2) 0.22542(17) 0.0395(7) Uani 1 1 d . . . O1 O 0.4305(3) 0.5546(2) 0.13035(16) 0.0598(8) Uani 1 1 d . . . O2 O 0.3229(4) 0.8974(2) 0.32893(17) 0.0642(8) Uani 1 1 d . . . C1 C 0.6035(5) 0.9439(3) -0.2233(2) 0.0505(10) Uani 1 1 d . . . H1 H 0.6291 0.9036 -0.2781 0.061 Uiso 1 1 calc R . . C2 C 0.5722(5) 0.8768(3) -0.1637(2) 0.0493(10) Uani 1 1 d . . . C3 C 0.5346(6) 0.9425(3) -0.0835(3) 0.0652(13) Uani 1 1 d . . . C4 C 0.5096(6) 0.8750(3) -0.0240(3) 0.0658(13) Uani 1 1 d . . . C5 C 0.5222(5) 0.7511(3) -0.0554(2) 0.0476(10) Uani 1 1 d . . . C6 C 0.4952(4) 0.6810(3) 0.0035(2) 0.0437(9) Uani 1 1 d . . . H6 H 0.5031 0.5972 -0.0136 0.052 Uiso 1 1 calc R . . C7 C 0.4568(4) 0.7366(3) 0.0871(2) 0.0406(9) Uani 1 1 d . . . C8 C 0.4449(5) 0.8646(3) 0.1175(2) 0.0443(9) Uani 1 1 d . . . C9 C 0.4729(6) 0.9312(3) 0.0599(3) 0.0655(13) Uani 1 1 d . . . C10 C 0.4219(4) 0.6642(3) 0.1465(2) 0.0402(9) Uani 1 1 d . . . C11 C 0.3633(5) 0.8556(3) 0.2581(2) 0.0445(9) Uani 1 1 d . . . C12 C 0.4040(5) 0.9295(3) 0.1999(2) 0.0429(9) Uani 1 1 d . . . C13 C 0.3172(5) 0.6490(3) 0.2758(2) 0.0410(9) Uani 1 1 d . . . C14 C 0.1498(5) 0.5898(3) 0.2432(2) 0.0495(10) Uani 1 1 d . . . C15 C 0.1029(6) 0.5092(4) 0.2878(3) 0.0664(12) Uani 1 1 d . . . H15 H -0.0076 0.4691 0.2682 0.080 Uiso 1 1 calc R . . C16 C 0.2160(7) 0.4874(4) 0.3601(3) 0.0801(15) Uani 1 1 d . . . H16 H 0.1825 0.4318 0.3883 0.096 Uiso 1 1 calc R . . C17 C 0.3783(6) 0.5474(4) 0.3911(3) 0.0769(14) Uani 1 1 d . . . H17 H 0.4537 0.5320 0.4405 0.092 Uiso 1 1 calc R . . C18 C 0.4333(5) 0.6308(3) 0.3504(2) 0.0521(10) Uani 1 1 d . . . C19 C 0.6149(6) 0.6963(4) 0.3884(3) 0.0704(13) Uani 1 1 d . . . H19 H 0.6329 0.7451 0.3480 0.085 Uiso 1 1 calc R . . C20 C 0.7386(7) 0.6026(5) 0.3850(4) 0.1063(18) Uani 1 1 d . . . H20A H 0.8500 0.6448 0.3968 0.159 Uiso 1 1 calc R . . H20B H 0.7059 0.5415 0.3242 0.159 Uiso 1 1 calc R . . H20C H 0.7372 0.5631 0.4318 0.159 Uiso 1 1 calc R . . C21 C 0.6481(7) 0.7847(5) 0.4869(3) 0.1056(18) Uani 1 1 d . . . H21A H 0.5776 0.8474 0.4858 0.158 Uiso 1 1 calc R . . H21B H 0.7640 0.8227 0.5099 0.158 Uiso 1 1 calc R . . H21C H 0.6237 0.7400 0.5272 0.158 Uiso 1 1 calc R . . C22 C 0.0228(5) 0.6132(4) 0.1636(3) 0.0693(13) Uani 1 1 d . . . H22 H 0.0855 0.6464 0.1277 0.083 Uiso 1 1 calc R . . C23 C -0.0787(7) 0.7126(6) 0.2031(4) 0.122(2) Uani 1 1 d . . . H23A H -0.1473 0.6806 0.2353 0.182 Uiso 1 1 calc R . . H23B H -0.1491 0.7343 0.1526 0.182 Uiso 1 1 calc R . . H23C H -0.0027 0.7846 0.2461 0.182 Uiso 1 1 calc R . . C24 C -0.0930(7) 0.4970(6) 0.0968(4) 0.134(2) Uani 1 1 d . . . H24A H -0.0280 0.4322 0.0815 0.201 Uiso 1 1 calc R . . H24B H -0.1517 0.5129 0.0407 0.201 Uiso 1 1 calc R . . H24C H -0.1729 0.4721 0.1260 0.201 Uiso 1 1 calc R . . C25 C 0.2028(7) 0.9108(8) 0.5499(4) 0.099(4) Uani 0.50 1 d PGU A 1 H25A H 0.2350 0.9443 0.5076 0.119 Uiso 0.50 1 calc PR A 1 C26 C 0.1402(7) 0.9829(4) 0.6186(6) 0.090(3) Uani 0.50 1 d PGU A 1 H26A H 0.1305 1.0646 0.6223 0.108 Uiso 0.50 1 calc PR A 1 C27 C 0.0921(6) 0.9328(7) 0.6819(4) 0.108(4) Uani 0.50 1 d PGU A 1 H27A H 0.0502 0.9810 0.7279 0.129 Uiso 0.50 1 calc PR A 1 C28 C 0.1066(7) 0.8107(8) 0.6765(4) 0.110(4) Uani 0.50 1 d PGU A 1 H28A H 0.0744 0.7772 0.7189 0.132 Uiso 0.50 1 calc PR A 1 C29 C 0.1692(7) 0.7386(4) 0.6078(6) 0.111(4) Uani 0.50 1 d PGU A 1 H29A H 0.1789 0.6569 0.6041 0.133 Uiso 0.50 1 calc PR A 1 C30 C 0.2173(6) 0.7887(8) 0.5445(4) 0.122(5) Uani 0.50 1 d PGU A 1 H30A H 0.2592 0.7405 0.4985 0.146 Uiso 0.50 1 calc PR A 1 C25' C 0.0877(6) 0.9549(5) 0.6534(5) 0.142(6) Uani 0.50 1 d PGU A 2 H25B H 0.0417 1.0235 0.6791 0.171 Uiso 0.50 1 calc PR A 2 C26' C 0.0908(7) 0.8567(9) 0.6897(3) 0.160(6) Uani 0.50 1 d PGU A 2 H26B H 0.0467 0.8596 0.7397 0.192 Uiso 0.50 1 calc PR A 2 C27' C 0.1596(8) 0.7541(6) 0.6514(6) 0.116(5) Uani 0.50 1 d PGU A 2 H27B H 0.1616 0.6884 0.6757 0.140 Uiso 0.50 1 calc PR A 2 C28' C 0.2254(7) 0.7497(5) 0.5767(6) 0.128(5) Uani 0.50 1 d PGU A 2 H28B H 0.2715 0.6811 0.5511 0.153 Uiso 0.50 1 calc PR A 2 C29' C 0.2224(6) 0.8480(9) 0.5404(3) 0.142(6) Uani 0.50 1 d PGU A 2 H29B H 0.2664 0.8451 0.4905 0.170 Uiso 0.50 1 calc PR A 2 C30' C 0.1535(7) 0.9505(6) 0.5788(5) 0.139(6) Uani 0.50 1 d PGU A 2 H30B H 0.1515 1.0163 0.5545 0.167 Uiso 0.50 1 calc PR A 2 C31 C 0.9465(11) 0.9763(14) 0.0675(6) 0.161(3) Uani 1 1 d U . . H31 H 0.9073 0.9609 0.1150 0.193 Uiso 1 1 calc R . . C32 C 0.9925(11) 0.8864(9) 0.0103(9) 0.151(3) Uani 1 1 d U . . H32 H 0.9885 0.8084 0.0179 0.181 Uiso 1 1 calc R . . C33 C 1.0457(11) 0.9075(12) -0.0596(7) 0.170(3) Uani 1 1 d . . . H33 H 1.0766 0.8441 -0.1019 0.205 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0984(9) 0.0272(4) 0.0489(6) 0.0117(4) 0.0420(6) 0.0170(5) N1 0.056(2) 0.0309(14) 0.0364(16) 0.0144(12) 0.0174(15) 0.0076(14) O1 0.104(2) 0.0332(13) 0.0596(16) 0.0230(12) 0.0419(16) 0.0220(14) O2 0.114(2) 0.0445(15) 0.0522(16) 0.0185(12) 0.0502(16) 0.0184(15) C1 0.083(3) 0.0354(19) 0.041(2) 0.0113(16) 0.031(2) 0.013(2) C2 0.082(3) 0.0276(17) 0.049(2) 0.0130(16) 0.035(2) 0.0136(19) C3 0.127(4) 0.0345(19) 0.059(2) 0.0202(18) 0.062(3) 0.025(2) C4 0.129(4) 0.0323(19) 0.062(2) 0.0220(18) 0.062(3) 0.026(2) C5 0.077(3) 0.0308(18) 0.046(2) 0.0136(16) 0.033(2) 0.0145(19) C6 0.066(3) 0.0284(17) 0.045(2) 0.0145(16) 0.0251(19) 0.0134(18) C7 0.055(3) 0.0315(18) 0.0395(19) 0.0144(15) 0.0163(18) 0.0092(17) C8 0.069(3) 0.0319(17) 0.0402(19) 0.0148(15) 0.0246(19) 0.0104(18) C9 0.131(4) 0.0300(19) 0.058(2) 0.0176(18) 0.059(3) 0.023(2) C10 0.054(3) 0.0307(18) 0.040(2) 0.0145(16) 0.0159(18) 0.0098(18) C11 0.065(3) 0.0364(19) 0.038(2) 0.0137(16) 0.0220(19) 0.0077(19) C12 0.061(3) 0.0336(18) 0.039(2) 0.0130(16) 0.0217(19) 0.0073(18) C13 0.056(3) 0.0370(19) 0.0376(19) 0.0186(16) 0.0188(19) 0.0062(19) C14 0.059(3) 0.049(2) 0.044(2) 0.0196(18) 0.016(2) 0.006(2) C15 0.073(3) 0.064(3) 0.069(3) 0.031(2) 0.026(3) -0.005(2) C16 0.099(4) 0.074(3) 0.081(3) 0.053(3) 0.024(3) -0.004(3) C17 0.087(4) 0.091(3) 0.069(3) 0.058(3) 0.015(3) 0.014(3) C18 0.064(3) 0.054(2) 0.045(2) 0.0273(19) 0.014(2) 0.010(2) C19 0.057(3) 0.096(3) 0.065(3) 0.046(3) 0.007(2) 0.005(3) C20 0.080(4) 0.147(5) 0.105(4) 0.056(4) 0.023(3) 0.039(4) C21 0.100(4) 0.112(4) 0.075(4) 0.010(3) 0.004(3) -0.013(3) C22 0.056(3) 0.093(3) 0.061(3) 0.038(3) 0.009(2) -0.004(3) C23 0.098(5) 0.155(6) 0.133(5) 0.069(5) 0.030(4) 0.066(4) C24 0.124(5) 0.139(5) 0.091(4) 0.036(4) -0.033(4) -0.047(4) C25 0.095(7) 0.075(6) 0.135(7) 0.012(5) 0.063(6) 0.028(5) C26 0.130(7) 0.081(6) 0.071(6) 0.023(5) 0.051(5) 0.012(5) C27 0.157(8) 0.077(6) 0.099(6) 0.045(6) 0.034(6) 0.018(6) C28 0.143(8) 0.077(6) 0.109(7) 0.029(6) 0.033(6) 0.020(6) C29 0.122(8) 0.102(7) 0.123(8) 0.039(6) 0.046(6) 0.044(6) C30 0.117(8) 0.090(7) 0.165(8) 0.037(6) 0.049(6) 0.040(6) C25' 0.174(9) 0.118(8) 0.130(8) 0.031(7) 0.040(7) 0.033(7) C26' 0.181(9) 0.153(9) 0.142(9) 0.035(7) 0.050(7) 0.037(8) C27' 0.125(8) 0.111(8) 0.114(8) 0.028(6) 0.042(6) 0.022(7) C28' 0.138(8) 0.125(8) 0.145(8) 0.058(7) 0.064(7) 0.024(6) C29' 0.139(9) 0.148(9) 0.155(8) 0.053(7) 0.061(7) 0.044(7) C30' 0.150(9) 0.130(9) 0.151(9) 0.056(7) 0.054(7) 0.023(7) C31 0.183(7) 0.174(7) 0.132(6) 0.063(6) 0.042(5) 0.017(6) C32 0.155(6) 0.140(6) 0.151(6) 0.063(6) 0.011(5) 0.025(5) C33 0.178(8) 0.178(11) 0.134(8) 0.026(7) 0.033(6) 0.034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.777(3) . ? S1 C2 1.791(3) . ? N1 C11 1.417(4) . ? N1 C10 1.417(4) . ? N1 C13 1.461(4) . ? O1 C10 1.217(3) . ? O2 C11 1.209(4) . ? C1 C12 1.398(4) 2_675 ? C1 C2 1.415(4) . ? C1 H1 0.9300 . ? C2 C3 1.382(4) . ? C3 C9 1.395(4) 2_675 ? C3 C4 1.401(5) . ? C4 C5 1.382(4) . ? C4 C9 1.399(5) . ? C5 C6 1.420(4) . ? C6 C7 1.399(4) . ? C6 H6 0.9300 . ? C7 C8 1.423(4) . ? C7 C10 1.466(4) . ? C8 C9 1.377(4) . ? C8 C12 1.422(4) . ? C9 C3 1.395(4) 2_675 ? C11 C12 1.478(4) . ? C12 C1 1.398(4) 2_675 ? C13 C18 1.386(5) . ? C13 C14 1.401(5) . ? C14 C15 1.386(5) . ? C14 C22 1.513(5) . ? C15 C16 1.368(6) . ? C15 H15 0.9300 . ? C16 C17 1.369(6) . ? C16 H16 0.9300 . ? C17 C18 1.392(5) . ? C17 H17 0.9300 . ? C18 C19 1.524(5) . ? C19 C21 1.518(6) . ? C19 C20 1.539(6) . ? C19 H19 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C24 1.515(6) . ? C22 C23 1.545(6) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.3900 . ? C25 C30 1.3900 . ? C25 H25A 0.9300 . ? C26 C27 1.3900 . ? C26 H26A 0.9300 . ? C27 C28 1.3900 . ? C27 H27A 0.9300 . ? C28 C29 1.3900 . ? C28 H28A 0.9300 . ? C29 C30 1.3900 . ? C29 H29A 0.9300 . ? C30 H30A 0.9300 . ? C25' C26' 1.3900 . ? C25' C30' 1.3900 . ? C25' H25B 0.9300 . ? C26' C27' 1.3900 . ? C26' H26B 0.9300 . ? C27' C28' 1.3900 . ? C27' H27B 0.9300 . ? C28' C29' 1.3900 . ? C28' H28B 0.9300 . ? C29' C30' 1.3900 . ? C29' H29B 0.9300 . ? C30' H30B 0.9300 . ? C31 C32 1.305(10) . ? C31 C33 1.366(10) 2_775 ? C31 H31 0.9300 . ? C32 C33 1.343(10) . ? C32 H32 0.9300 . ? C33 C31 1.366(10) 2_775 ? C33 H33 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C2 92.93(15) . . ? C11 N1 C10 127.4(3) . . ? C11 N1 C13 117.9(2) . . ? C10 N1 C13 114.6(2) . . ? C12 C1 C2 120.1(3) 2_675 . ? C12 C1 H1 119.9 2_675 . ? C2 C1 H1 119.9 . . ? C3 C2 C1 116.8(3) . . ? C3 C2 S1 107.7(2) . . ? C1 C2 S1 135.5(3) . . ? C2 C3 C9 123.3(3) . 2_675 ? C2 C3 C4 115.7(3) . . ? C9 C3 C4 121.0(3) 2_675 . ? C5 C4 C9 123.7(3) . . ? C5 C4 C3 115.0(3) . . ? C9 C4 C3 121.3(3) . . ? C4 C5 C6 115.8(3) . . ? C4 C5 S1 108.5(2) . . ? C6 C5 S1 135.7(2) . . ? C7 C6 C5 120.7(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 122.2(3) . . ? C6 C7 C10 121.1(3) . . ? C8 C7 C10 116.7(3) . . ? C9 C8 C12 117.0(3) . . ? C9 C8 C7 116.3(3) . . ? C12 C8 C7 126.7(3) . . ? C8 C9 C3 120.9(3) . 2_675 ? C8 C9 C4 121.4(3) . . ? C3 C9 C4 117.8(3) 2_675 . ? O1 C10 N1 119.6(3) . . ? O1 C10 C7 123.9(3) . . ? N1 C10 C7 116.4(3) . . ? O2 C11 N1 119.9(3) . . ? O2 C11 C12 124.1(3) . . ? N1 C11 C12 116.0(3) . . ? C1 C12 C8 121.9(3) 2_675 . ? C1 C12 C11 121.5(3) 2_675 . ? C8 C12 C11 116.6(3) . . ? C18 C13 C14 122.6(3) . . ? C18 C13 N1 119.5(3) . . ? C14 C13 N1 117.8(3) . . ? C15 C14 C13 117.3(4) . . ? C15 C14 C22 120.6(4) . . ? C13 C14 C22 122.1(3) . . ? C16 C15 C14 121.3(4) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.1(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 121.6(4) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C13 C18 C17 117.0(4) . . ? C13 C18 C19 123.5(3) . . ? C17 C18 C19 119.4(4) . . ? C21 C19 C18 111.1(4) . . ? C21 C19 C20 111.3(4) . . ? C18 C19 C20 111.1(4) . . ? C21 C19 H19 107.7 . . ? C18 C19 H19 107.7 . . ? C20 C19 H19 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 C24 113.1(4) . . ? C14 C22 C23 109.9(4) . . ? C24 C22 C23 111.0(4) . . ? C14 C22 H22 107.5 . . ? C24 C22 H22 107.5 . . ? C23 C22 H22 107.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 120.0 . . ? C26 C25 H25A 120.0 . . ? C30 C25 H25A 120.0 . . ? C25 C26 C27 120.0 . . ? C25 C26 H26A 120.0 . . ? C27 C26 H26A 120.0 . . ? C28 C27 C26 120.0 . . ? C28 C27 H27A 120.0 . . ? C26 C27 H27A 120.0 . . ? C27 C28 C29 120.0 . . ? C27 C28 H28A 120.0 . . ? C29 C28 H28A 120.0 . . ? C28 C29 C30 120.0 . . ? C28 C29 H29A 120.0 . . ? C30 C29 H29A 120.0 . . ? C29 C30 C25 120.0 . . ? C29 C30 H30A 120.0 . . ? C25 C30 H30A 120.0 . . ? C26' C25' C30' 120.0 . . ? C26' C25' H25B 120.0 . . ? C30' C25' H25B 120.0 . . ? C25' C26' C27' 120.0 . . ? C25' C26' H26B 120.0 . . ? C27' C26' H26B 120.0 . . ? C28' C27' C26' 120.0 . . ? C28' C27' H27B 120.0 . . ? C26' C27' H27B 120.0 . . ? C27' C28' C29' 120.0 . . ? C27' C28' H28B 120.0 . . ? C29' C28' H28B 120.0 . . ? C28' C29' C30' 120.0 . . ? C28' C29' H29B 120.0 . . ? C30' C29' H29B 120.0 . . ? C29' C30' C25' 120.0 . . ? C29' C30' H30B 120.0 . . ? C25' C30' H30B 120.0 . . ? C32 C31 C33 121.8(9) . 2_775 ? C32 C31 H31 119.1 . . ? C33 C31 H31 119.1 2_775 . ? C31 C32 C33 119.3(9) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C32 C33 C31 118.8(9) . 2_775 ? C32 C33 H33 120.6 . . ? C31 C33 H33 120.6 2_775 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 C1 C2 C3 0.1(6) 2_675 . . . ? C12 C1 C2 S1 -178.7(3) 2_675 . . . ? C5 S1 C2 C3 -0.5(3) . . . . ? C5 S1 C2 C1 178.4(4) . . . . ? C1 C2 C3 C9 -0.2(7) . . . 2_675 ? S1 C2 C3 C9 179.0(4) . . . 2_675 ? C1 C2 C3 C4 -177.9(4) . . . . ? S1 C2 C3 C4 1.2(5) . . . . ? C2 C3 C4 C5 -1.5(7) . . . . ? C9 C3 C4 C5 -179.4(4) 2_675 . . . ? C2 C3 C4 C9 179.2(4) . . . . ? C9 C3 C4 C9 1.4(8) 2_675 . . . ? C9 C4 C5 C6 0.0(7) . . . . ? C3 C4 C5 C6 -179.3(4) . . . . ? C9 C4 C5 S1 -179.7(4) . . . . ? C3 C4 C5 S1 1.0(5) . . . . ? C2 S1 C5 C4 -0.3(3) . . . . ? C2 S1 C5 C6 -179.9(4) . . . . ? C4 C5 C6 C7 0.6(6) . . . . ? S1 C5 C6 C7 -179.8(3) . . . . ? C5 C6 C7 C8 -0.7(6) . . . . ? C5 C6 C7 C10 177.5(3) . . . . ? C6 C7 C8 C9 0.2(6) . . . . ? C10 C7 C8 C9 -178.1(3) . . . . ? C6 C7 C8 C12 178.8(4) . . . . ? C10 C7 C8 C12 0.6(6) . . . . ? C12 C8 C9 C3 1.7(6) . . . 2_675 ? C7 C8 C9 C3 -179.6(4) . . . 2_675 ? C12 C8 C9 C4 -178.3(4) . . . . ? C7 C8 C9 C4 0.5(6) . . . . ? C5 C4 C9 C8 -0.6(8) . . . . ? C3 C4 C9 C8 178.6(4) . . . . ? C5 C4 C9 C3 179.5(4) . . . 2_675 ? C3 C4 C9 C3 -1.3(8) . . . 2_675 ? C11 N1 C10 O1 176.0(3) . . . . ? C13 N1 C10 O1 -5.6(5) . . . . ? C11 N1 C10 C7 -5.7(5) . . . . ? C13 N1 C10 C7 172.7(3) . . . . ? C6 C7 C10 O1 3.3(6) . . . . ? C8 C7 C10 O1 -178.5(4) . . . . ? C6 C7 C10 N1 -175.0(3) . . . . ? C8 C7 C10 N1 3.3(5) . . . . ? C10 N1 C11 O2 -177.3(3) . . . . ? C13 N1 C11 O2 4.4(5) . . . . ? C10 N1 C11 C12 3.7(5) . . . . ? C13 N1 C11 C12 -174.6(3) . . . . ? C9 C8 C12 C1 -1.6(6) . . . 2_675 ? C7 C8 C12 C1 179.7(4) . . . 2_675 ? C9 C8 C12 C11 176.1(4) . . . . ? C7 C8 C12 C11 -2.5(6) . . . . ? O2 C11 C12 C1 -0.7(6) . . . 2_675 ? N1 C11 C12 C1 178.3(3) . . . 2_675 ? O2 C11 C12 C8 -178.4(4) . . . . ? N1 C11 C12 C8 0.5(5) . . . . ? C11 N1 C13 C18 -89.4(4) . . . . ? C10 N1 C13 C18 92.0(4) . . . . ? C11 N1 C13 C14 93.6(4) . . . . ? C10 N1 C13 C14 -84.9(4) . . . . ? C18 C13 C14 C15 -0.9(5) . . . . ? N1 C13 C14 C15 176.0(3) . . . . ? C18 C13 C14 C22 178.2(4) . . . . ? N1 C13 C14 C22 -5.0(5) . . . . ? C13 C14 C15 C16 -0.6(6) . . . . ? C22 C14 C15 C16 -179.7(4) . . . . ? C14 C15 C16 C17 1.2(7) . . . . ? C15 C16 C17 C18 -0.3(7) . . . . ? C14 C13 C18 C17 1.7(5) . . . . ? N1 C13 C18 C17 -175.1(3) . . . . ? C14 C13 C18 C19 -178.6(4) . . . . ? N1 C13 C18 C19 4.6(5) . . . . ? C16 C17 C18 C13 -1.1(6) . . . . ? C16 C17 C18 C19 179.2(4) . . . . ? C13 C18 C19 C21 113.3(4) . . . . ? C17 C18 C19 C21 -67.1(5) . . . . ? C13 C18 C19 C20 -122.3(4) . . . . ? C17 C18 C19 C20 57.3(5) . . . . ? C15 C14 C22 C24 -41.2(6) . . . . ? C13 C14 C22 C24 139.8(4) . . . . ? C15 C14 C22 C23 83.5(5) . . . . ? C13 C14 C22 C23 -95.6(5) . . . . ? C30 C25 C26 C27 0.0 . . . . ? C25 C26 C27 C28 0.0 . . . . ? C26 C27 C28 C29 0.0 . . . . ? C27 C28 C29 C30 0.0 . . . . ? C28 C29 C30 C25 0.0 . . . . ? C26 C25 C30 C29 0.0 . . . . ? C30' C25' C26' C27' 0.0 . . . . ? C25' C26' C27' C28' 0.0 . . . . ? C26' C27' C28' C29' 0.0 . . . . ? C27' C28' C29' C30' 0.0 . . . . ? C28' C29' C30' C25' 0.0 . . . . ? C26' C25' C30' C29' 0.0 . . . . ? C33 C31 C32 C33 -1.5(17) 2_775 . . . ? C31 C32 C33 C31 1.5(16) . . . 2_775 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.232 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.048 # Attachment '5PhMe.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 612067' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34.50 H31 N O2 S' _chemical_formula_weight 523.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.264(2) _cell_length_b 11.438(3) _cell_length_c 15.204(4) _cell_angle_alpha 101.119(4) _cell_angle_beta 100.521(4) _cell_angle_gamma 91.278(4) _cell_volume 1383.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4490 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 26.38 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9427 _exptl_absorpt_correction_T_max 0.9566 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7866 _diffrn_reflns_av_R_equivalents 0.0135 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 26.39 _reflns_number_total 5578 _reflns_number_gt 4502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.5380P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5578 _refine_ls_number_parameters 352 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.82503(19) 0.41072(13) 0.71899(10) 0.0319(3) Uani 1 1 d . . . S1 S 0.28598(7) 0.17767(4) 0.34328(3) 0.04292(18) Uani 1 1 d . . . O1 O 0.6872(2) 0.52503(12) 0.62694(10) 0.0492(4) Uani 1 1 d . . . O2 O 0.95886(19) 0.30412(13) 0.81887(10) 0.0491(4) Uani 1 1 d . . . C1 C 0.1990(2) -0.08159(17) 0.28690(13) 0.0376(4) Uani 1 1 d . . . H1A H 0.1238 -0.0754 0.2347 0.045 Uiso 1 1 calc R . . C2 C 0.2838(3) 0.02222(17) 0.34395(13) 0.0403(5) Uani 1 1 d . . . C3 C 0.3908(3) 0.00588(18) 0.42044(15) 0.0534(6) Uani 1 1 d . . . C4 C 0.4700(3) 0.11009(18) 0.47714(15) 0.0530(6) Uani 1 1 d . . . C5 C 0.4317(3) 0.21407(17) 0.44776(13) 0.0391(5) Uani 1 1 d . . . C6 C 0.5113(2) 0.32097(16) 0.50286(12) 0.0339(4) Uani 1 1 d . . . H6A H 0.4896 0.3938 0.4859 0.041 Uiso 1 1 calc R . . C7 C 0.6233(2) 0.31656(15) 0.58335(12) 0.0316(4) Uani 1 1 d . . . C8 C 0.6601(2) 0.20803(16) 0.61227(13) 0.0362(4) Uani 1 1 d . . . C9 C 0.5804(3) 0.10548(18) 0.55718(15) 0.0519(6) Uani 1 1 d . . . C10 C 0.7092(2) 0.42602(16) 0.64199(12) 0.0325(4) Uani 1 1 d . . . C11 C 0.8606(2) 0.30263(16) 0.74913(12) 0.0330(4) Uani 1 1 d . . . C12 C 0.7723(2) 0.19367(16) 0.69141(12) 0.0331(4) Uani 1 1 d . . . C13 C 0.9193(2) 0.51817(16) 0.77194(13) 0.0330(4) Uani 1 1 d . . . C14 C 0.8673(2) 0.58053(17) 0.84856(14) 0.0379(4) Uani 1 1 d . . . C15 C 0.9598(3) 0.68354(19) 0.89649(16) 0.0488(5) Uani 1 1 d . . . H15A H 0.9290 0.7265 0.9487 0.059 Uiso 1 1 calc R . . C16 C 1.0963(3) 0.7231(2) 0.86812(17) 0.0543(6) Uani 1 1 d . . . H16A H 1.1563 0.7926 0.9007 0.065 Uiso 1 1 calc R . . C17 C 1.1438(3) 0.6600(2) 0.79179(17) 0.0508(6) Uani 1 1 d . . . H17A H 1.2358 0.6880 0.7730 0.061 Uiso 1 1 calc R . . C18 C 1.0581(3) 0.55522(19) 0.74176(14) 0.0410(5) Uani 1 1 d . . . C19 C 1.1188(3) 0.4826(2) 0.66124(17) 0.0575(6) Uani 1 1 d . . . H19A H 1.0266 0.4291 0.6243 0.069 Uiso 1 1 calc R . . C20 C 1.1769(6) 0.5580(4) 0.6007(3) 0.1110(14) Uani 1 1 d . . . H20A H 1.0891 0.6050 0.5791 0.167 Uiso 1 1 calc R . . H20B H 1.2092 0.5072 0.5496 0.167 Uiso 1 1 calc R . . H20C H 1.2694 0.6099 0.6348 0.167 Uiso 1 1 calc R . . C21 C 1.2562(5) 0.4053(4) 0.6947(3) 0.0976(12) Uani 1 1 d . . . H21A H 1.2179 0.3576 0.7331 0.146 Uiso 1 1 calc R . . H21B H 1.3502 0.4556 0.7287 0.146 Uiso 1 1 calc R . . H21C H 1.2867 0.3540 0.6432 0.146 Uiso 1 1 calc R . . C22 C 0.7160(3) 0.5406(2) 0.88058(15) 0.0460(5) Uani 1 1 d . . . H22A H 0.6669 0.4676 0.8381 0.055 Uiso 1 1 calc R . . C23 C 0.7587(4) 0.5122(3) 0.97545(19) 0.0666(7) Uani 1 1 d . . . H23A H 0.8387 0.4526 0.9757 0.100 Uiso 1 1 calc R . . H23B H 0.6609 0.4827 0.9918 0.100 Uiso 1 1 calc R . . H23C H 0.8033 0.5832 1.0187 0.100 Uiso 1 1 calc R . . C24 C 0.5879(3) 0.6358(3) 0.8780(2) 0.0723(8) Uani 1 1 d . . . H24A H 0.5615 0.6518 0.8174 0.108 Uiso 1 1 calc R . . H24B H 0.6323 0.7078 0.9202 0.108 Uiso 1 1 calc R . . H24C H 0.4899 0.6073 0.8946 0.108 Uiso 1 1 calc R . . C25 C 0.2282(5) 1.0080(4) 0.0770(3) 0.1015(12) Uani 1 1 d . . . H25A H 0.2475 1.0925 0.0831 0.152 Uiso 1 1 calc R . . H25B H 0.1543 0.9931 0.1160 0.152 Uiso 1 1 calc R . . H25C H 0.1801 0.9732 0.0147 0.152 Uiso 1 1 calc R . . C26 C 0.3869(4) 0.9539(3) 0.10332(19) 0.0706(8) Uani 1 1 d . . . C27 C 0.5319(5) 1.0227(3) 0.1307(3) 0.0965(11) Uani 1 1 d . . . H27A H 0.5315 1.1048 0.1343 0.116 Uiso 1 1 calc R . . C28 C 0.6776(5) 0.9707(4) 0.1530(3) 0.1089(13) Uani 1 1 d . . . H28A H 0.7755 1.0182 0.1703 0.131 Uiso 1 1 calc R . . C29 C 0.6823(5) 0.8519(4) 0.1502(3) 0.0957(11) Uani 1 1 d . . . H29A H 0.7820 0.8180 0.1660 0.115 Uiso 1 1 calc R . . C30 C 0.5389(5) 0.7828(3) 0.1241(2) 0.0854(9) Uani 1 1 d . . . H30A H 0.5408 0.7010 0.1222 0.102 Uiso 1 1 calc R . . C31 C 0.3913(4) 0.8326(3) 0.1005(2) 0.0736(8) Uani 1 1 d . . . H31A H 0.2941 0.7844 0.0826 0.088 Uiso 1 1 calc R . . C32 C 1.1187(9) 0.0640(7) 0.5736(5) 0.217(4) Uani 1 1 d DU . . H32A H 1.1999 0.1064 0.6201 0.260 Uiso 1 1 calc R . . C33 C 1.0224(9) 0.1193(5) 0.5139(5) 0.186(3) Uani 1 1 d DU B . H33A H 1.0329 0.2022 0.5249 0.224 Uiso 1 1 calc R . . C34 C 0.9096(8) 0.0625(6) 0.4380(4) 0.205(4) Uani 1 1 d DU . . H34A H 0.8532 0.1059 0.3953 0.246 Uiso 0.50 1 d PR A 2 C35 C 0.813(2) 0.1229(13) 0.3746(11) 0.258(10) Uani 0.50 1 d PDU B 1 H35A H 0.7417 0.0658 0.3285 0.388 Uiso 0.50 1 calc PR B 1 H35B H 0.8848 0.1648 0.3465 0.388 Uiso 0.50 1 calc PR B 1 H35C H 0.7479 0.1788 0.4063 0.388 Uiso 0.50 1 calc PR B 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0341(8) 0.0255(7) 0.0326(8) 0.0036(6) 0.0000(6) -0.0011(6) S1 0.0560(3) 0.0272(3) 0.0380(3) 0.01061(19) -0.0146(2) -0.0002(2) O1 0.0610(10) 0.0260(7) 0.0514(9) 0.0095(6) -0.0140(7) -0.0024(6) O2 0.0561(9) 0.0353(7) 0.0447(8) 0.0076(6) -0.0184(7) -0.0029(6) C1 0.0445(11) 0.0323(10) 0.0311(9) 0.0076(7) -0.0066(8) 0.0015(8) C2 0.0521(12) 0.0269(9) 0.0369(10) 0.0099(8) -0.0084(9) 0.0022(8) C3 0.0752(16) 0.0253(10) 0.0460(12) 0.0091(9) -0.0248(11) -0.0025(10) C4 0.0737(15) 0.0257(10) 0.0463(12) 0.0088(9) -0.0240(11) -0.0027(10) C5 0.0480(11) 0.0288(9) 0.0347(9) 0.0097(7) -0.0101(8) 0.0021(8) C6 0.0417(10) 0.0242(8) 0.0342(9) 0.0090(7) -0.0001(8) 0.0028(7) C7 0.0363(9) 0.0252(9) 0.0314(9) 0.0061(7) 0.0014(7) 0.0011(7) C8 0.0447(11) 0.0261(9) 0.0334(9) 0.0061(7) -0.0042(8) 0.0014(8) C9 0.0715(15) 0.0272(10) 0.0442(11) 0.0091(8) -0.0236(11) -0.0026(10) C10 0.0355(9) 0.0279(9) 0.0323(9) 0.0065(7) 0.0019(7) 0.0008(7) C11 0.0352(9) 0.0289(9) 0.0322(9) 0.0049(7) 0.0007(7) 0.0016(7) C12 0.0381(10) 0.0280(9) 0.0303(9) 0.0058(7) -0.0010(8) 0.0006(7) C13 0.0323(9) 0.0260(9) 0.0370(9) 0.0055(7) -0.0017(7) -0.0016(7) C14 0.0375(10) 0.0304(9) 0.0415(10) 0.0033(8) 0.0007(8) 0.0008(8) C15 0.0536(13) 0.0356(11) 0.0491(12) -0.0048(9) 0.0029(10) -0.0016(9) C16 0.0529(13) 0.0368(11) 0.0631(14) 0.0018(10) -0.0041(11) -0.0151(10) C17 0.0426(12) 0.0475(12) 0.0595(14) 0.0120(10) 0.0024(10) -0.0136(10) C18 0.0380(10) 0.0407(11) 0.0422(11) 0.0099(8) 0.0016(8) -0.0028(8) C19 0.0513(13) 0.0672(16) 0.0522(13) 0.0030(11) 0.0168(11) -0.0118(12) C20 0.149(4) 0.122(3) 0.076(2) 0.025(2) 0.054(2) -0.020(3) C21 0.091(2) 0.101(3) 0.105(3) 0.005(2) 0.042(2) 0.034(2) C22 0.0426(11) 0.0447(12) 0.0467(12) -0.0016(9) 0.0099(9) -0.0013(9) C23 0.0617(16) 0.0759(18) 0.0678(17) 0.0242(14) 0.0171(13) -0.0002(14) C24 0.0506(15) 0.089(2) 0.0812(19) 0.0218(16) 0.0164(14) 0.0198(14) C25 0.122(3) 0.111(3) 0.082(2) 0.035(2) 0.025(2) 0.048(3) C26 0.094(2) 0.0685(18) 0.0562(15) 0.0202(13) 0.0209(15) 0.0180(16) C27 0.113(3) 0.064(2) 0.116(3) 0.035(2) 0.015(2) 0.001(2) C28 0.096(3) 0.102(3) 0.135(4) 0.053(3) 0.008(3) -0.007(2) C29 0.090(3) 0.110(3) 0.099(3) 0.044(2) 0.021(2) 0.026(2) C30 0.103(3) 0.069(2) 0.088(2) 0.0211(17) 0.021(2) 0.0196(19) C31 0.090(2) 0.0644(18) 0.0664(17) 0.0125(14) 0.0167(16) 0.0044(16) C32 0.236(7) 0.200(7) 0.218(7) -0.045(6) 0.146(6) -0.029(6) C33 0.207(7) 0.164(5) 0.190(6) -0.044(5) 0.132(5) -0.027(5) C34 0.225(7) 0.181(6) 0.221(7) -0.036(5) 0.161(6) -0.041(5) C35 0.257(13) 0.270(13) 0.252(13) 0.034(9) 0.074(9) 0.021(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C10 1.412(2) . ? N1 C11 1.418(2) . ? N1 C13 1.453(2) . ? S1 C2 1.780(2) . ? S1 C5 1.7804(19) . ? O1 C10 1.209(2) . ? O2 C11 1.209(2) . ? C1 C12 1.399(3) 2_656 ? C1 C2 1.413(3) . ? C1 H1A 0.9300 . ? C2 C3 1.373(3) . ? C3 C9 1.395(3) 2_656 ? C3 C4 1.399(3) . ? C4 C5 1.373(3) . ? C4 C9 1.392(3) . ? C5 C6 1.413(3) . ? C6 C7 1.403(2) . ? C6 H6A 0.9300 . ? C7 C8 1.416(2) . ? C7 C10 1.471(2) . ? C8 C9 1.377(3) . ? C8 C12 1.418(3) . ? C9 C3 1.395(3) 2_656 ? C11 C12 1.470(2) . ? C12 C1 1.399(3) 2_656 ? C13 C14 1.388(3) . ? C13 C18 1.397(3) . ? C14 C15 1.389(3) . ? C14 C22 1.514(3) . ? C15 C16 1.376(3) . ? C15 H15A 0.9300 . ? C16 C17 1.370(4) . ? C16 H16A 0.9300 . ? C17 C18 1.390(3) . ? C17 H17A 0.9300 . ? C18 C19 1.514(3) . ? C19 C20 1.507(4) . ? C19 C21 1.529(5) . ? C19 H19A 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.520(4) . ? C22 C24 1.536(3) . ? C22 H22A 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.484(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.370(5) . ? C26 C31 1.382(4) . ? C27 C28 1.370(6) . ? C27 H27A 0.9300 . ? C28 C29 1.353(5) . ? C28 H28A 0.9300 . ? C29 C30 1.361(5) . ? C29 H29A 0.9300 . ? C30 C31 1.375(5) . ? C30 H30A 0.9300 . ? C31 H31A 0.9300 . ? C32 C33 1.356(7) . ? C32 C34 1.432(6) 2_756 ? C32 H32A 0.9300 . ? C33 C34 1.383(7) . ? C33 H33A 0.9300 . ? C34 C35 1.430(8) . ? C34 C32 1.432(6) 2_756 ? C34 H34A 0.9540 . ? C35 H34A 0.4847 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N1 C11 127.31(15) . . ? C10 N1 C13 115.76(14) . . ? C11 N1 C13 116.93(14) . . ? C2 S1 C5 92.74(9) . . ? C12 C1 C2 120.29(17) 2_656 . ? C12 C1 H1A 119.9 2_656 . ? C2 C1 H1A 119.9 . . ? C3 C2 C1 116.38(17) . . ? C3 C2 S1 108.23(14) . . ? C1 C2 S1 135.39(15) . . ? C2 C3 C9 123.71(19) . 2_656 ? C2 C3 C4 115.40(18) . . ? C9 C3 C4 120.88(19) 2_656 . ? C5 C4 C9 123.66(19) . . ? C5 C4 C3 115.42(18) . . ? C9 C4 C3 120.92(19) . . ? C4 C5 C6 116.89(17) . . ? C4 C5 S1 108.21(14) . . ? C6 C5 S1 134.90(14) . . ? C7 C6 C5 119.59(16) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C6 C7 C8 122.34(16) . . ? C6 C7 C10 121.01(16) . . ? C8 C7 C10 116.65(16) . . ? C9 C8 C7 116.68(17) . . ? C9 C8 C12 116.52(17) . . ? C7 C8 C12 126.79(17) . . ? C8 C9 C4 120.83(19) . . ? C8 C9 C3 120.96(19) . 2_656 ? C4 C9 C3 118.20(19) . 2_656 ? O1 C10 N1 119.84(16) . . ? O1 C10 C7 123.88(16) . . ? N1 C10 C7 116.28(15) . . ? O2 C11 N1 119.82(16) . . ? O2 C11 C12 123.96(17) . . ? N1 C11 C12 116.22(15) . . ? C1 C12 C8 122.13(16) 2_656 . ? C1 C12 C11 121.19(16) 2_656 . ? C8 C12 C11 116.66(16) . . ? C14 C13 C18 122.84(17) . . ? C14 C13 N1 119.40(17) . . ? C18 C13 N1 117.76(17) . . ? C13 C14 C15 117.47(19) . . ? C13 C14 C22 122.66(17) . . ? C15 C14 C22 119.87(19) . . ? C16 C15 C14 121.2(2) . . ? C16 C15 H15A 119.4 . . ? C14 C15 H15A 119.4 . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 121.6(2) . . ? C16 C17 H17A 119.2 . . ? C18 C17 H17A 119.2 . . ? C17 C18 C13 116.9(2) . . ? C17 C18 C19 120.8(2) . . ? C13 C18 C19 122.22(18) . . ? C20 C19 C18 113.2(3) . . ? C20 C19 C21 110.2(3) . . ? C18 C19 C21 110.0(2) . . ? C20 C19 H19A 107.7 . . ? C18 C19 H19A 107.7 . . ? C21 C19 H19A 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 C23 111.93(19) . . ? C14 C22 C24 110.3(2) . . ? C23 C22 C24 110.7(2) . . ? C14 C22 H22A 107.9 . . ? C23 C22 H22A 107.9 . . ? C24 C22 H22A 107.9 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 118.6(3) . . ? C27 C26 C25 121.0(3) . . ? C31 C26 C25 120.4(3) . . ? C28 C27 C26 120.1(3) . . ? C28 C27 H27A 120.0 . . ? C26 C27 H27A 120.0 . . ? C29 C28 C27 121.5(4) . . ? C29 C28 H28A 119.3 . . ? C27 C28 H28A 119.3 . . ? C28 C29 C30 119.0(4) . . ? C28 C29 H29A 120.5 . . ? C30 C29 H29A 120.5 . . ? C29 C30 C31 120.6(3) . . ? C29 C30 H30A 119.7 . . ? C31 C30 H30A 119.7 . . ? C30 C31 C26 120.2(3) . . ? C30 C31 H31A 119.9 . . ? C26 C31 H31A 119.9 . . ? C33 C32 C34 117.2(6) . 2_756 ? C33 C32 H32A 121.4 . . ? C34 C32 H32A 121.4 2_756 . ? C32 C33 C34 125.3(6) . . ? C32 C33 H33A 117.3 . . ? C34 C33 H33A 117.3 . . ? C33 C34 C35 124.1(7) . . ? C33 C34 C32 117.2(6) . 2_756 ? C35 C34 C32 118.6(7) . 2_756 ? C33 C34 H34A 121.3 . . ? C35 C34 H34A 4.6 . . ? C32 C34 H34A 121.6 2_756 . ? C34 C35 H34A 9.1 . . ? C34 C35 H35A 109.5 . . ? H34A C35 H35A 115.0 . . ? C34 C35 H35B 109.5 . . ? H34A C35 H35B 100.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H34A C35 H35C 112.4 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 C1 C2 C3 -1.0(3) 2_656 . . . ? C12 C1 C2 S1 -179.86(19) 2_656 . . . ? C5 S1 C2 C3 -0.4(2) . . . . ? C5 S1 C2 C1 178.6(2) . . . . ? C1 C2 C3 C9 0.7(4) . . . 2_656 ? S1 C2 C3 C9 179.9(2) . . . 2_656 ? C1 C2 C3 C4 -178.4(2) . . . . ? S1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C9 C3 C4 C5 180.0(3) 2_656 . . . ? C2 C3 C4 C9 179.5(3) . . . . ? C9 C3 C4 C9 0.3(5) 2_656 . . . ? C9 C4 C5 C6 0.4(4) . . . . ? C3 C4 C5 C6 -179.2(2) . . . . ? C9 C4 C5 S1 -179.8(2) . . . . ? C3 C4 C5 S1 0.5(3) . . . . ? C2 S1 C5 C4 -0.1(2) . . . . ? C2 S1 C5 C6 179.6(2) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? S1 C5 C6 C7 -179.72(18) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C5 C6 C7 C10 179.59(18) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C10 C7 C8 C9 -179.7(2) . . . . ? C6 C7 C8 C12 179.2(2) . . . . ? C10 C7 C8 C12 -0.6(3) . . . . ? C7 C8 C9 C4 0.2(4) . . . . ? C12 C8 C9 C4 -178.9(2) . . . . ? C7 C8 C9 C3 179.6(2) . . . 2_656 ? C12 C8 C9 C3 0.5(4) . . . 2_656 ? C5 C4 C9 C8 -0.5(5) . . . . ? C3 C4 C9 C8 179.1(3) . . . . ? C5 C4 C9 C3 -179.9(3) . . . 2_656 ? C3 C4 C9 C3 -0.3(5) . . . 2_656 ? C11 N1 C10 O1 176.82(19) . . . . ? C13 N1 C10 O1 -4.2(3) . . . . ? C11 N1 C10 C7 -4.1(3) . . . . ? C13 N1 C10 C7 174.89(16) . . . . ? C6 C7 C10 O1 1.9(3) . . . . ? C8 C7 C10 O1 -178.3(2) . . . . ? C6 C7 C10 N1 -177.09(17) . . . . ? C8 C7 C10 N1 2.7(3) . . . . ? C10 N1 C11 O2 -176.96(19) . . . . ? C13 N1 C11 O2 4.0(3) . . . . ? C10 N1 C11 C12 3.0(3) . . . . ? C13 N1 C11 C12 -176.04(16) . . . . ? C9 C8 C12 C1 -0.2(3) . . . 2_656 ? C7 C8 C12 C1 -179.2(2) . . . 2_656 ? C9 C8 C12 C11 178.5(2) . . . . ? C7 C8 C12 C11 -0.5(3) . . . . ? O2 C11 C12 C1 -1.9(3) . . . 2_656 ? N1 C11 C12 C1 178.21(18) . . . 2_656 ? O2 C11 C12 C8 179.4(2) . . . . ? N1 C11 C12 C8 -0.5(3) . . . . ? C10 N1 C13 C14 95.9(2) . . . . ? C11 N1 C13 C14 -84.9(2) . . . . ? C10 N1 C13 C18 -82.9(2) . . . . ? C11 N1 C13 C18 96.2(2) . . . . ? C18 C13 C14 C15 -0.4(3) . . . . ? N1 C13 C14 C15 -179.22(17) . . . . ? C18 C13 C14 C22 179.49(19) . . . . ? N1 C13 C14 C22 0.7(3) . . . . ? C13 C14 C15 C16 1.0(3) . . . . ? C22 C14 C15 C16 -178.9(2) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C16 C17 C18 C13 1.1(3) . . . . ? C16 C17 C18 C19 -176.0(2) . . . . ? C14 C13 C18 C17 -0.6(3) . . . . ? N1 C13 C18 C17 178.20(18) . . . . ? C14 C13 C18 C19 176.5(2) . . . . ? N1 C13 C18 C19 -4.7(3) . . . . ? C17 C18 C19 C20 -43.0(4) . . . . ? C13 C18 C19 C20 140.0(3) . . . . ? C17 C18 C19 C21 80.7(3) . . . . ? C13 C18 C19 C21 -96.2(3) . . . . ? C13 C14 C22 C23 118.1(2) . . . . ? C15 C14 C22 C23 -62.0(3) . . . . ? C13 C14 C22 C24 -118.2(2) . . . . ? C15 C14 C22 C24 61.7(3) . . . . ? C31 C26 C27 C28 1.3(6) . . . . ? C25 C26 C27 C28 -178.6(4) . . . . ? C26 C27 C28 C29 -1.3(7) . . . . ? C27 C28 C29 C30 0.5(7) . . . . ? C28 C29 C30 C31 0.2(6) . . . . ? C29 C30 C31 C26 -0.1(5) . . . . ? C27 C26 C31 C30 -0.6(5) . . . . ? C25 C26 C31 C30 179.3(3) . . . . ? C34 C32 C33 C34 -6.3(13) 2_756 . . . ? C32 C33 C34 C35 -178.0(13) . . . . ? C32 C33 C34 C32 6.3(13) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.500 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.046 # Attachment '5pyrene.CIF' data_5pyrene _database_code_depnum_ccdc_archive 'CCDC 612068' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C83 H64 Cl6 N2 O4 S2' _chemical_formula_sum 'C83 H64 Cl6 N2 O4 S2' _chemical_formula_weight 1430.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.435(2) _cell_length_b 17.055(3) _cell_length_c 20.962(4) _cell_angle_alpha 108.740(3) _cell_angle_beta 101.183(3) _cell_angle_gamma 94.073(2) _cell_volume 3430.1(12) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 9822 _cell_measurement_theta_min 1.3 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1484 _exptl_absorpt_coefficient_mu 0.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8854 _exptl_absorpt_correction_T_max 0.9236 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30321 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 27.86 _reflns_number_total 16044 _reflns_number_gt 12085 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0799P)^2^+0.2848P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16044 _refine_ls_number_parameters 902 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1507 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.58814(5) 0.72683(3) 0.54563(2) 0.02107(11) Uani 1 1 d . . . S2 S 1.02297(5) 1.22830(3) 1.04970(2) 0.02354(12) Uani 1 1 d . . . N1 N 0.37443(15) 0.46518(9) 0.22312(8) 0.0182(3) Uani 1 1 d . . . N2 N 0.82599(15) 0.96963(10) 0.72605(8) 0.0190(3) Uani 1 1 d . . . O1 O 0.43461(14) 0.60444(8) 0.24734(7) 0.0255(3) Uani 1 1 d . . . O2 O 0.32392(14) 0.32339(8) 0.19154(7) 0.0273(3) Uani 1 1 d . . . O3 O 0.84453(15) 1.11113(9) 0.75370(7) 0.0307(3) Uani 1 1 d . . . O4 O 0.80856(14) 0.82727(8) 0.69177(7) 0.0273(3) Uani 1 1 d . . . C1 C 0.61235(17) 0.67096(11) 0.66691(10) 0.0186(4) Uani 1 1 d . . . H1A H 0.6413 0.7253 0.7004 0.022 Uiso 1 1 calc R . . C2 C 0.58283(18) 0.65979(11) 0.59533(9) 0.0181(4) Uani 1 1 d . . . C3 C 0.54137(17) 0.57871(11) 0.55016(9) 0.0181(4) Uani 1 1 d . . . C4 C 0.51421(18) 0.56919(11) 0.47976(9) 0.0184(4) Uani 1 1 d . . . C5 C 0.53185(18) 0.64295(11) 0.46580(10) 0.0190(4) Uani 1 1 d . . . C6 C 0.50272(18) 0.63541(11) 0.39483(10) 0.0192(4) Uani 1 1 d . . . H6A H 0.5123 0.6838 0.3821 0.023 Uiso 1 1 calc R . . C7 C 0.45974(17) 0.55637(11) 0.34350(9) 0.0173(4) Uani 1 1 d . . . C8 C 0.44454(16) 0.48155(11) 0.35945(9) 0.0164(3) Uani 1 1 d . . . C9 C 0.47330(17) 0.49072(11) 0.42906(9) 0.0179(4) Uani 1 1 d . . . C10 C 0.42504(18) 0.54680(11) 0.26970(10) 0.0196(4) Uani 1 1 d . . . C11 C 0.36414(17) 0.38966(11) 0.23846(10) 0.0186(4) Uani 1 1 d . . . C12 C 0.40158(17) 0.39916(11) 0.31194(9) 0.0167(3) Uani 1 1 d . . . C13 C 0.32098(18) 0.45591(11) 0.15127(9) 0.0200(4) Uani 1 1 d . . . C14 C 0.40161(19) 0.43561(12) 0.10399(10) 0.0223(4) Uani 1 1 d . . . C15 C 0.3430(2) 0.42072(13) 0.03484(11) 0.0286(4) Uani 1 1 d . . . H15A H 0.3945 0.4059 0.0012 0.034 Uiso 1 1 calc R . . C16 C 0.2106(2) 0.42703(13) 0.01402(11) 0.0309(5) Uani 1 1 d . . . H16A H 0.1720 0.4155 -0.0336 0.037 Uiso 1 1 calc R . . C17 C 0.1350(2) 0.45014(13) 0.06250(11) 0.0282(4) Uani 1 1 d . . . H17A H 0.0451 0.4556 0.0479 0.034 Uiso 1 1 calc R . . C18 C 0.18826(19) 0.46555(12) 0.13229(10) 0.0229(4) Uani 1 1 d . . . C19 C 0.1046(2) 0.49115(13) 0.18527(11) 0.0289(4) Uani 1 1 d . . . H19A H 0.1656 0.5106 0.2322 0.035 Uiso 1 1 calc R . . C20 C 0.0309(3) 0.56344(17) 0.17913(18) 0.0586(8) Uani 1 1 d . . . H20A H 0.0940 0.6106 0.1821 0.088 Uiso 1 1 calc R . . H20B H -0.0152 0.5808 0.2168 0.088 Uiso 1 1 calc R . . H20C H -0.0333 0.5453 0.1345 0.088 Uiso 1 1 calc R . . C21 C 0.0087(3) 0.41710(15) 0.18076(14) 0.0429(6) Uani 1 1 d . . . H21A H 0.0574 0.3712 0.1848 0.064 Uiso 1 1 calc R . . H21B H -0.0557 0.3984 0.1362 0.064 Uiso 1 1 calc R . . H21C H -0.0376 0.4339 0.2184 0.064 Uiso 1 1 calc R . . C22 C 0.54793(19) 0.43374(13) 0.12694(11) 0.0263(4) Uani 1 1 d . . . H22A H 0.5672 0.4424 0.1775 0.032 Uiso 1 1 calc R . . C23 C 0.5900(2) 0.35093(16) 0.09079(15) 0.0491(7) Uani 1 1 d . . . H23A H 0.5369 0.3056 0.0973 0.074 Uiso 1 1 calc R . . H23B H 0.6835 0.3517 0.1104 0.074 Uiso 1 1 calc R . . H23C H 0.5768 0.3419 0.0412 0.074 Uiso 1 1 calc R . . C24 C 0.6285(2) 0.50546(17) 0.11777(18) 0.0568(8) Uani 1 1 d . . . H24A H 0.7227 0.5033 0.1328 0.085 Uiso 1 1 calc R . . H24B H 0.6067 0.5588 0.1457 0.085 Uiso 1 1 calc R . . H24C H 0.6081 0.5006 0.0689 0.085 Uiso 1 1 calc R . . C25 C 1.09832(18) 1.16954(12) 1.16845(10) 0.0206(4) Uani 1 1 d . . . H25A H 1.1187 1.2239 1.2026 0.025 Uiso 1 1 calc R . . C26 C 1.05396(18) 1.15930(11) 1.09762(10) 0.0195(4) Uani 1 1 d . . . C27 C 1.02746(17) 1.07840(11) 1.05118(9) 0.0186(4) Uani 1 1 d . . . C28 C 0.98684(17) 1.07042(11) 0.98155(10) 0.0188(4) Uani 1 1 d . . . C29 C 0.97713(18) 1.14510(11) 0.96897(10) 0.0199(4) Uani 1 1 d . . . C30 C 0.93562(18) 1.13907(12) 0.89909(10) 0.0205(4) Uani 1 1 d . . . H30A H 0.9282 1.1883 0.8875 0.025 Uiso 1 1 calc R . . C31 C 0.90546(17) 1.06045(11) 0.84691(9) 0.0182(4) Uani 1 1 d . . . C32 C 0.91658(17) 0.98458(11) 0.86083(9) 0.0174(4) Uani 1 1 d . . . C33 C 0.95823(17) 0.99245(11) 0.92992(9) 0.0178(4) Uani 1 1 d . . . C34 C 0.85873(18) 1.05240(12) 0.77406(10) 0.0205(4) Uani 1 1 d . . . C35 C 0.83944(18) 0.89377(12) 0.73944(10) 0.0198(4) Uani 1 1 d . . . C36 C 0.88805(17) 0.90211(11) 0.81218(9) 0.0177(4) Uani 1 1 d . . . C37 C 0.76409(18) 0.96000(11) 0.65510(9) 0.0191(4) Uani 1 1 d . . . C38 C 0.84087(18) 0.94859(12) 0.60602(10) 0.0219(4) Uani 1 1 d . . . C39 C 0.7759(2) 0.93610(13) 0.53830(11) 0.0275(4) Uani 1 1 d . . . H39A H 0.8254 0.9283 0.5037 0.033 Uiso 1 1 calc R . . C40 C 0.6410(2) 0.93482(13) 0.52004(11) 0.0287(4) Uani 1 1 d . . . H40A H 0.5985 0.9251 0.4733 0.034 Uiso 1 1 calc R . . C41 C 0.5681(2) 0.94768(12) 0.56998(11) 0.0265(4) Uani 1 1 d . . . H41A H 0.4756 0.9474 0.5572 0.032 Uiso 1 1 calc R . . C42 C 0.62757(18) 0.96107(11) 0.63854(10) 0.0213(4) Uani 1 1 d . . . C43 C 0.54604(19) 0.97545(13) 0.69279(11) 0.0273(4) Uani 1 1 d . . . H43A H 0.6074 0.9843 0.7383 0.033 Uiso 1 1 calc R . . C44 C 0.4803(3) 1.05422(15) 0.69945(14) 0.0437(6) Uani 1 1 d . . . H44A H 0.5478 1.1022 0.7095 0.066 Uiso 1 1 calc R . . H44B H 0.4340 1.0645 0.7372 0.066 Uiso 1 1 calc R . . H44C H 0.4170 1.0464 0.6560 0.066 Uiso 1 1 calc R . . C45 C 0.4445(2) 0.89893(15) 0.67716(14) 0.0438(6) Uani 1 1 d . . . H45A H 0.4895 0.8496 0.6732 0.066 Uiso 1 1 calc R . . H45B H 0.3810 0.8900 0.6335 0.066 Uiso 1 1 calc R . . H45C H 0.3980 0.9080 0.7147 0.066 Uiso 1 1 calc R . . C46 C 0.9886(2) 0.94970(14) 0.62529(11) 0.0295(5) Uani 1 1 d . . . H46A H 1.0138 0.9612 0.6763 0.035 Uiso 1 1 calc R . . C47 C 1.0267(3) 0.86556(19) 0.5903(2) 0.0839(13) Uani 1 1 d . . . H47A H 1.1227 0.8681 0.6037 0.126 Uiso 1 1 calc R . . H47B H 0.9989 0.8507 0.5400 0.126 Uiso 1 1 calc R . . H47C H 0.9833 0.8232 0.6045 0.126 Uiso 1 1 calc R . . C48 C 1.0636(3) 1.01820(18) 0.61120(18) 0.0605(8) Uani 1 1 d . . . H48A H 1.1585 1.0166 0.6244 0.091 Uiso 1 1 calc R . . H48B H 1.0432 1.0724 0.6382 0.091 Uiso 1 1 calc R . . H48C H 1.0383 1.0104 0.5618 0.091 Uiso 1 1 calc R . . C49 C 0.7824(2) 0.9204(2) 0.18855(17) 0.0581(9) Uani 1 1 d . . . H49A H 0.8064 0.9026 0.2273 0.070 Uiso 1 1 calc R . . C50 C 0.7478(2) 0.86159(19) 0.12240(17) 0.0501(7) Uani 1 1 d . . . H50A H 0.7479 0.8039 0.1163 0.060 Uiso 1 1 calc R . . C51 C 0.7125(2) 0.88608(16) 0.06394(14) 0.0384(6) Uani 1 1 d . . . C52 C 0.6781(2) 0.82863(16) -0.00482(15) 0.0436(6) Uani 1 1 d . . . H52A H 0.6787 0.7707 -0.0124 0.052 Uiso 1 1 calc R . . C53 C 0.6441(2) 0.85414(15) -0.06033(14) 0.0399(6) Uani 1 1 d . . . H53A H 0.6224 0.8139 -0.1057 0.048 Uiso 1 1 calc R . . C54 C 0.64083(19) 0.94079(14) -0.05111(12) 0.0318(5) Uani 1 1 d . . . C55 C 0.6051(2) 0.96976(17) -0.10659(13) 0.0404(6) Uani 1 1 d . . . H55A H 0.5804 0.9309 -0.1525 0.048 Uiso 1 1 calc R . . C56 C 0.6052(2) 1.05408(18) -0.09545(14) 0.0440(6) Uani 1 1 d . . . H56A H 0.5802 1.0724 -0.1338 0.053 Uiso 1 1 calc R . . C57 C 0.6414(2) 1.11234(17) -0.02892(14) 0.0416(6) Uani 1 1 d . . . H57A H 0.6419 1.1702 -0.0221 0.050 Uiso 1 1 calc R . . C58 C 0.6771(2) 1.08650(14) 0.02802(13) 0.0336(5) Uani 1 1 d . . . C59 C 0.7158(2) 1.14454(16) 0.09808(14) 0.0421(6) Uani 1 1 d . . . H59A H 0.7173 1.2027 0.1061 0.051 Uiso 1 1 calc R . . C60 C 0.7491(2) 1.11886(17) 0.15168(14) 0.0452(6) Uani 1 1 d . . . H60A H 0.7744 1.1591 0.1970 0.054 Uiso 1 1 calc R . . C61 C 0.7480(2) 1.03176(17) 0.14288(13) 0.0394(6) Uani 1 1 d . . . C62 C 0.7824(2) 1.0043(2) 0.19872(14) 0.0497(7) Uani 1 1 d . . . H62A H 0.8061 1.0438 0.2444 0.060 Uiso 1 1 calc R . . C63 C 0.71214(19) 0.97283(14) 0.07467(12) 0.0322(5) Uani 1 1 d . . . C64 C 0.67703(18) 0.99996(13) 0.01683(11) 0.0278(4) Uani 1 1 d . . . C65 C 0.7270(2) 0.3590(2) 0.27869(14) 0.0507(7) Uani 1 1 d . . . H65A H 0.7042 0.3272 0.2307 0.061 Uiso 1 1 calc R . . C66 C 0.7581(2) 0.44470(19) 0.30014(13) 0.0429(6) Uani 1 1 d . . . H66A H 0.7560 0.4713 0.2666 0.051 Uiso 1 1 calc R . . C67 C 0.7925(2) 0.49298(16) 0.37021(13) 0.0363(5) Uani 1 1 d . . . C68 C 0.8260(2) 0.58233(16) 0.39455(15) 0.0437(6) Uani 1 1 d . . . H68A H 0.8245 0.6105 0.3620 0.052 Uiso 1 1 calc R . . C69 C 0.8599(2) 0.62748(16) 0.46362(15) 0.0418(6) Uani 1 1 d . . . H69A H 0.8815 0.6866 0.4782 0.050 Uiso 1 1 calc R . . C70 C 0.8636(2) 0.58831(15) 0.51446(13) 0.0356(5) Uani 1 1 d . . . C71 C 0.8975(2) 0.63297(16) 0.58465(14) 0.0415(6) Uani 1 1 d . . . H71A H 0.9185 0.6921 0.6000 0.050 Uiso 1 1 calc R . . C72 C 0.9016(2) 0.59319(17) 0.63313(14) 0.0432(6) Uani 1 1 d . . . H72A H 0.9259 0.6252 0.6811 0.052 Uiso 1 1 calc R . . C73 C 0.8706(2) 0.50772(16) 0.61198(12) 0.0371(5) Uani 1 1 d . . . H73A H 0.8741 0.4811 0.6456 0.045 Uiso 1 1 calc R . . C74 C 0.8339(2) 0.45914(15) 0.54135(12) 0.0344(5) Uani 1 1 d . . . C75 C 0.7997(2) 0.37033(15) 0.51715(14) 0.0389(6) Uani 1 1 d . . . H75A H 0.8008 0.3425 0.5499 0.047 Uiso 1 1 calc R . . C76 C 0.7658(2) 0.32463(15) 0.44870(13) 0.0370(5) Uani 1 1 d . . . H76A H 0.7440 0.2656 0.4346 0.044 Uiso 1 1 calc R . . C77 C 0.7623(2) 0.36351(15) 0.39700(13) 0.0359(5) Uani 1 1 d . . . C78 C 0.7288(2) 0.31878(17) 0.32692(14) 0.0454(6) Uani 1 1 d . . . H78A H 0.7066 0.2597 0.3114 0.055 Uiso 1 1 calc R . . C79 C 0.79535(19) 0.45285(14) 0.41991(12) 0.0301(5) Uani 1 1 d . . . C80 C 0.83026(19) 0.49919(14) 0.49202(12) 0.0293(5) Uani 1 1 d . . . C81 C 0.3178(3) 0.6735(2) 0.12415(18) 0.0727(11) Uani 1 1 d . . . H81A H 0.3330 0.6174 0.1256 0.087 Uiso 1 1 calc R . . H81B H 0.2885 0.7039 0.1664 0.087 Uiso 1 1 calc R . . C83 C 0.3087(3) 0.24975(16) 0.71812(13) 0.0441(6) Uani 1 1 d . . . H83A H 0.3510 0.2078 0.7351 0.053 Uiso 1 1 calc R . . H83B H 0.3742 0.3009 0.7334 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.19368(6) 0.66244(4) 0.05125(3) 0.04345(16) Uani 1 1 d . . . Cl2 Cl 0.46697(6) 0.72837(5) 0.12325(4) 0.05437(19) Uani 1 1 d . . . C82 C 0.2005(12) 0.8277(6) 0.3691(3) 0.065(4) Uani 0.629(14) 1 d PD A 1 H82A H 0.2360 0.8834 0.3696 0.077 Uiso 0.629(14) 1 calc PR A 1 H82B H 0.1085 0.8140 0.3412 0.077 Uiso 0.629(14) 1 calc PR A 1 Cl3 Cl 0.2928(3) 0.75407(18) 0.3264(2) 0.0549(8) Uani 0.629(14) 1 d PD A 1 Cl4 Cl 0.1962(5) 0.83597(19) 0.45244(16) 0.0693(7) Uani 0.629(14) 1 d PD A 1 C82' C 0.2186(19) 0.8328(7) 0.3680(5) 0.051(5) Uani 0.371(14) 1 d PD A 2 H82C H 0.2681 0.8822 0.3643 0.061 Uiso 0.371(14) 1 calc PR A 2 H82D H 0.1229 0.8346 0.3545 0.061 Uiso 0.371(14) 1 calc PR A 2 Cl3' Cl 0.2613(15) 0.7402(7) 0.3166(5) 0.135(3) Uani 0.371(14) 1 d PD A 2 Cl4' Cl 0.2620(17) 0.8295(3) 0.4508(3) 0.096(3) Uani 0.371(14) 1 d PD A 2 Cl5 Cl 0.26371(7) 0.21023(4) 0.62714(3) 0.05113(18) Uani 1 1 d . . . Cl6 Cl 0.17245(8) 0.27362(5) 0.75433(4) 0.0669(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0312(2) 0.0143(2) 0.0170(2) 0.00563(18) 0.0045(2) 0.00043(19) S2 0.0358(3) 0.0159(2) 0.0182(2) 0.00674(18) 0.0033(2) 0.0036(2) N1 0.0212(7) 0.0195(8) 0.0143(8) 0.0067(6) 0.0035(6) 0.0021(6) N2 0.0209(7) 0.0200(8) 0.0155(8) 0.0076(6) 0.0008(6) 0.0015(6) O1 0.0361(8) 0.0203(7) 0.0209(7) 0.0107(6) 0.0038(6) -0.0002(6) O2 0.0400(8) 0.0208(7) 0.0164(7) 0.0044(6) 0.0014(6) -0.0020(6) O3 0.0480(9) 0.0219(7) 0.0216(8) 0.0114(6) 0.0001(7) 0.0037(7) O4 0.0405(8) 0.0203(7) 0.0167(7) 0.0054(6) 0.0005(6) -0.0029(6) C1 0.0211(8) 0.0160(8) 0.0176(9) 0.0040(7) 0.0052(7) 0.0014(7) C2 0.0224(9) 0.0161(8) 0.0164(9) 0.0055(7) 0.0058(7) 0.0032(7) C3 0.0221(9) 0.0164(8) 0.0155(9) 0.0050(7) 0.0044(7) 0.0027(7) C4 0.0230(9) 0.0168(9) 0.0163(9) 0.0071(7) 0.0040(7) 0.0029(7) C5 0.0236(9) 0.0157(8) 0.0175(9) 0.0058(7) 0.0038(7) 0.0029(7) C6 0.0231(9) 0.0171(9) 0.0187(9) 0.0075(7) 0.0060(8) 0.0022(7) C7 0.0197(8) 0.0173(9) 0.0159(9) 0.0064(7) 0.0048(7) 0.0025(7) C8 0.0151(8) 0.0173(8) 0.0168(9) 0.0058(7) 0.0035(7) 0.0021(7) C9 0.0222(9) 0.0150(8) 0.0163(9) 0.0057(7) 0.0035(7) 0.0020(7) C10 0.0210(9) 0.0198(9) 0.0188(10) 0.0072(7) 0.0051(8) 0.0031(7) C11 0.0209(8) 0.0183(9) 0.0171(9) 0.0069(7) 0.0045(7) 0.0025(7) C12 0.0177(8) 0.0179(8) 0.0139(9) 0.0048(7) 0.0038(7) 0.0016(7) C13 0.0252(9) 0.0198(9) 0.0140(9) 0.0078(7) -0.0004(8) 0.0006(8) C14 0.0259(9) 0.0241(10) 0.0185(10) 0.0103(8) 0.0039(8) 0.0030(8) C15 0.0361(11) 0.0323(11) 0.0185(10) 0.0104(9) 0.0066(9) 0.0026(9) C16 0.0380(11) 0.0337(11) 0.0194(10) 0.0117(9) -0.0009(9) 0.0024(10) C17 0.0256(10) 0.0292(11) 0.0265(11) 0.0109(9) -0.0038(9) 0.0027(9) C18 0.0242(9) 0.0189(9) 0.0231(10) 0.0064(8) 0.0018(8) 0.0013(8) C19 0.0239(9) 0.0311(11) 0.0271(11) 0.0036(9) 0.0052(9) 0.0079(9) C20 0.0565(17) 0.0442(16) 0.094(3) 0.0306(16) 0.0426(18) 0.0260(14) C21 0.0517(15) 0.0365(13) 0.0459(15) 0.0094(11) 0.0313(13) 0.0073(11) C22 0.0255(10) 0.0366(11) 0.0194(10) 0.0118(9) 0.0072(8) 0.0051(9) C23 0.0352(13) 0.0398(14) 0.0641(19) 0.0096(13) 0.0050(13) 0.0107(11) C24 0.0296(12) 0.0488(16) 0.098(3) 0.0364(17) 0.0101(14) 0.0000(12) C25 0.0251(9) 0.0176(9) 0.0183(10) 0.0057(7) 0.0043(8) 0.0011(7) C26 0.0232(9) 0.0174(9) 0.0188(10) 0.0071(7) 0.0047(8) 0.0044(7) C27 0.0212(8) 0.0188(9) 0.0166(9) 0.0071(7) 0.0041(7) 0.0036(7) C28 0.0211(8) 0.0191(9) 0.0172(9) 0.0078(7) 0.0037(7) 0.0032(7) C29 0.0253(9) 0.0165(9) 0.0192(10) 0.0077(7) 0.0055(8) 0.0037(7) C30 0.0255(9) 0.0189(9) 0.0185(10) 0.0092(8) 0.0035(8) 0.0036(8) C31 0.0196(8) 0.0190(9) 0.0176(9) 0.0090(7) 0.0029(7) 0.0027(7) C32 0.0154(8) 0.0195(9) 0.0184(9) 0.0083(7) 0.0035(7) 0.0015(7) C33 0.0204(8) 0.0176(9) 0.0156(9) 0.0062(7) 0.0034(7) 0.0024(7) C34 0.0227(9) 0.0207(9) 0.0176(9) 0.0072(8) 0.0027(8) 0.0025(8) C35 0.0208(8) 0.0205(9) 0.0192(10) 0.0086(8) 0.0046(8) 0.0011(7) C36 0.0176(8) 0.0193(9) 0.0147(9) 0.0062(7) 0.0009(7) -0.0007(7) C37 0.0224(9) 0.0193(9) 0.0154(9) 0.0075(7) 0.0018(7) 0.0008(7) C38 0.0250(9) 0.0208(9) 0.0205(10) 0.0083(8) 0.0050(8) 0.0005(8) C39 0.0344(11) 0.0290(11) 0.0211(11) 0.0105(9) 0.0078(9) 0.0035(9) C40 0.0378(11) 0.0280(10) 0.0176(10) 0.0101(8) -0.0029(9) 0.0037(9) C41 0.0252(9) 0.0268(10) 0.0267(11) 0.0115(9) -0.0005(8) 0.0057(8) C42 0.0240(9) 0.0185(9) 0.0211(10) 0.0074(8) 0.0032(8) 0.0033(8) C43 0.0225(9) 0.0314(11) 0.0276(11) 0.0091(9) 0.0060(8) 0.0047(8) C44 0.0462(14) 0.0366(13) 0.0552(17) 0.0146(12) 0.0253(13) 0.0168(11) C45 0.0436(14) 0.0376(13) 0.0537(17) 0.0117(12) 0.0275(13) 0.0024(11) C46 0.0253(10) 0.0380(12) 0.0269(11) 0.0128(10) 0.0077(9) 0.0034(9) C47 0.0363(15) 0.0432(17) 0.148(4) 0.004(2) 0.0127(19) 0.0133(13) C48 0.0328(13) 0.0563(18) 0.097(3) 0.0415(18) 0.0054(15) -0.0074(13) C49 0.0317(13) 0.108(3) 0.060(2) 0.055(2) 0.0206(14) 0.0186(15) C50 0.0308(12) 0.0637(18) 0.076(2) 0.0435(17) 0.0235(14) 0.0122(12) C51 0.0228(10) 0.0475(14) 0.0534(16) 0.0247(13) 0.0145(11) 0.0078(10) C52 0.0262(11) 0.0370(13) 0.0700(19) 0.0187(13) 0.0159(12) 0.0039(10) C53 0.0263(11) 0.0378(13) 0.0481(15) 0.0027(11) 0.0130(11) 0.0004(10) C54 0.0198(9) 0.0400(13) 0.0341(13) 0.0076(10) 0.0116(9) 0.0049(9) C55 0.0233(10) 0.0608(17) 0.0338(13) 0.0098(12) 0.0105(10) 0.0052(11) C56 0.0289(11) 0.0680(18) 0.0470(16) 0.0318(14) 0.0128(11) 0.0143(12) C57 0.0305(11) 0.0468(14) 0.0587(17) 0.0268(13) 0.0183(12) 0.0134(11) C58 0.0199(9) 0.0378(12) 0.0429(14) 0.0122(11) 0.0095(10) 0.0056(9) C59 0.0278(11) 0.0374(13) 0.0531(17) 0.0026(12) 0.0121(11) 0.0075(10) C60 0.0272(11) 0.0531(16) 0.0441(16) 0.0007(13) 0.0094(11) 0.0063(11) C61 0.0193(10) 0.0634(17) 0.0362(14) 0.0141(12) 0.0112(10) 0.0101(11) C62 0.0272(11) 0.089(2) 0.0395(15) 0.0263(15) 0.0146(11) 0.0150(13) C63 0.0199(9) 0.0404(13) 0.0381(13) 0.0128(11) 0.0110(9) 0.0062(9) C64 0.0163(9) 0.0337(11) 0.0343(12) 0.0102(9) 0.0096(9) 0.0057(8) C65 0.0349(13) 0.075(2) 0.0310(14) 0.0045(13) 0.0067(11) 0.0040(13) C66 0.0269(11) 0.0752(19) 0.0285(13) 0.0190(13) 0.0074(10) 0.0105(12) C67 0.0220(10) 0.0521(15) 0.0388(14) 0.0192(12) 0.0076(10) 0.0106(10) C68 0.0318(12) 0.0477(15) 0.0643(19) 0.0310(14) 0.0165(12) 0.0151(11) C69 0.0335(12) 0.0358(13) 0.0636(18) 0.0216(13) 0.0178(12) 0.0123(10) C70 0.0233(10) 0.0364(12) 0.0476(15) 0.0123(11) 0.0116(10) 0.0076(9) C71 0.0290(11) 0.0362(13) 0.0515(16) 0.0048(12) 0.0085(11) 0.0054(10) C72 0.0266(11) 0.0545(16) 0.0377(14) 0.0018(12) 0.0067(10) 0.0057(11) C73 0.0239(10) 0.0587(16) 0.0292(12) 0.0142(11) 0.0076(9) 0.0081(11) C74 0.0230(10) 0.0429(13) 0.0379(13) 0.0128(11) 0.0094(9) 0.0078(10) C75 0.0306(11) 0.0392(13) 0.0529(16) 0.0193(12) 0.0160(11) 0.0091(10) C76 0.0297(11) 0.0302(12) 0.0529(16) 0.0132(11) 0.0160(11) 0.0035(9) C77 0.0242(10) 0.0442(14) 0.0391(14) 0.0108(11) 0.0123(10) 0.0056(10) C78 0.0325(12) 0.0466(15) 0.0456(16) 0.0001(12) 0.0116(12) -0.0014(11) C79 0.0181(9) 0.0407(12) 0.0336(12) 0.0126(10) 0.0093(9) 0.0086(9) C80 0.0175(9) 0.0386(12) 0.0329(12) 0.0118(10) 0.0078(9) 0.0083(9) C81 0.0422(15) 0.110(3) 0.078(2) 0.073(2) -0.0160(15) -0.0209(17) C83 0.0454(14) 0.0408(14) 0.0402(15) 0.0098(11) 0.0051(12) 0.0010(12) Cl1 0.0426(3) 0.0356(3) 0.0458(4) 0.0139(3) -0.0052(3) 0.0078(3) Cl2 0.0438(3) 0.0700(5) 0.0508(4) 0.0349(4) -0.0033(3) -0.0104(3) C82 0.080(5) 0.097(8) 0.035(5) 0.032(5) 0.021(4) 0.058(5) Cl3 0.0598(15) 0.0428(10) 0.0694(14) 0.0269(8) 0.0120(8) 0.0254(10) Cl4 0.122(2) 0.0594(10) 0.0458(10) 0.0353(9) 0.0299(13) 0.0217(12) C82' 0.093(11) 0.028(6) 0.041(9) 0.023(6) 0.021(7) 0.004(6) Cl3' 0.242(8) 0.133(5) 0.077(4) 0.058(4) 0.061(5) 0.142(5) Cl4' 0.194(8) 0.0381(15) 0.0307(16) 0.0126(12) -0.027(3) -0.006(3) Cl5 0.0661(4) 0.0422(3) 0.0378(4) 0.0117(3) 0.0070(3) -0.0158(3) Cl6 0.0631(5) 0.0706(5) 0.0663(5) 0.0124(4) 0.0249(4) 0.0282(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.776(2) . ? S1 C2 1.7816(18) . ? S2 C29 1.776(2) . ? S2 C26 1.7850(18) . ? N1 C10 1.412(2) . ? N1 C11 1.426(2) . ? N1 C13 1.454(2) . ? N2 C34 1.417(2) . ? N2 C35 1.420(2) . ? N2 C37 1.453(2) . ? O1 C10 1.223(2) . ? O2 C11 1.216(2) . ? O3 C34 1.216(2) . ? O4 C35 1.218(2) . ? C1 C12 1.410(2) 2_666 ? C1 C2 1.418(3) . ? C1 H1A 0.9500 . ? C2 C3 1.382(2) . ? C3 C9 1.395(2) 2_666 ? C3 C4 1.401(2) . ? C4 C5 1.388(2) . ? C4 C9 1.390(2) . ? C5 C6 1.421(3) . ? C6 C7 1.404(3) . ? C6 H6A 0.9500 . ? C7 C8 1.425(2) . ? C7 C10 1.471(3) . ? C8 C9 1.386(2) . ? C8 C12 1.416(2) . ? C9 C3 1.395(2) 2_666 ? C11 C12 1.466(2) . ? C12 C1 1.410(2) 2_666 ? C13 C14 1.398(3) . ? C13 C18 1.401(2) . ? C14 C15 1.392(3) . ? C14 C22 1.515(3) . ? C15 C16 1.388(3) . ? C15 H15A 0.9500 . ? C16 C17 1.382(3) . ? C16 H16A 0.9500 . ? C17 C18 1.391(3) . ? C17 H17A 0.9500 . ? C18 C19 1.518(3) . ? C19 C21 1.521(3) . ? C19 C20 1.525(3) . ? C19 H19A 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.514(3) . ? C22 C24 1.519(3) . ? C22 H22A 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C36 1.414(2) 2_777 ? C25 C26 1.416(3) . ? C25 H25A 0.9500 . ? C26 C27 1.381(3) . ? C27 C33 1.396(2) 2_777 ? C27 C28 1.397(2) . ? C28 C33 1.386(3) . ? C28 C29 1.388(2) . ? C29 C30 1.412(3) . ? C30 C31 1.399(3) . ? C30 H30A 0.9500 . ? C31 C32 1.423(2) . ? C31 C34 1.468(3) . ? C32 C33 1.388(3) . ? C32 C36 1.417(3) . ? C33 C27 1.396(2) 2_777 ? C35 C36 1.467(3) . ? C36 C25 1.414(2) 2_777 ? C37 C38 1.397(3) . ? C37 C42 1.402(2) . ? C38 C39 1.390(3) . ? C38 C46 1.513(3) . ? C39 C40 1.382(3) . ? C39 H39A 0.9500 . ? C40 C41 1.381(3) . ? C40 H40A 0.9500 . ? C41 C42 1.388(3) . ? C41 H41A 0.9500 . ? C42 C43 1.518(3) . ? C43 C45 1.525(3) . ? C43 C44 1.531(3) . ? C43 H43A 1.0000 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C48 1.499(3) . ? C46 C47 1.508(3) . ? C46 H46A 1.0000 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C62 1.377(4) . ? C49 C50 1.385(4) . ? C49 H49A 0.9500 . ? C50 C51 1.410(4) . ? C50 H50A 0.9500 . ? C51 C52 1.417(4) . ? C51 C63 1.424(3) . ? C52 C53 1.362(4) . ? C52 H52A 0.9500 . ? C53 C54 1.431(3) . ? C53 H53A 0.9500 . ? C54 C55 1.401(3) . ? C54 C64 1.415(3) . ? C55 C56 1.381(4) . ? C55 H55A 0.9500 . ? C56 C57 1.388(4) . ? C56 H56A 0.9500 . ? C57 C58 1.395(3) . ? C57 H57A 0.9500 . ? C58 C64 1.418(3) . ? C58 C59 1.442(3) . ? C59 C60 1.327(4) . ? C59 H59A 0.9500 . ? C60 C61 1.436(4) . ? C60 H60A 0.9500 . ? C61 C62 1.390(4) . ? C61 C63 1.418(3) . ? C62 H62A 0.9500 . ? C63 C64 1.425(3) . ? C65 C66 1.377(4) . ? C65 C78 1.391(4) . ? C65 H65A 0.9500 . ? C66 C67 1.393(3) . ? C66 H66A 0.9500 . ? C67 C79 1.416(3) . ? C67 C68 1.435(3) . ? C68 C69 1.364(4) . ? C68 H68A 0.9500 . ? C69 C70 1.424(3) . ? C69 H69A 0.9500 . ? C70 C71 1.382(4) . ? C70 C80 1.434(3) . ? C71 C72 1.388(4) . ? C71 H71A 0.9500 . ? C72 C73 1.374(4) . ? C72 H72A 0.9500 . ? C73 C74 1.404(3) . ? C73 H73A 0.9500 . ? C74 C80 1.407(3) . ? C74 C75 1.428(3) . ? C75 C76 1.355(3) . ? C75 H75A 0.9500 . ? C76 C77 1.437(3) . ? C76 H76A 0.9500 . ? C77 C78 1.380(3) . ? C77 C79 1.436(3) . ? C78 H78A 0.9500 . ? C79 C80 1.421(3) . ? C81 Cl1 1.749(3) . ? C81 Cl2 1.765(3) . ? C81 H81A 0.9900 . ? C81 H81B 0.9900 . ? C83 Cl6 1.751(3) . ? C83 Cl5 1.759(3) . ? C83 H83A 0.9900 . ? C83 H83B 0.9900 . ? C82 Cl4 1.717(6) . ? C82 Cl3 1.758(6) . ? C82 H82A 0.9900 . ? C82 H82B 0.9900 . ? C82' Cl4' 1.727(9) . ? C82' Cl3' 1.746(8) . ? C82' H82C 0.9900 . ? C82' H82D 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C2 92.96(9) . . ? C29 S2 C26 93.15(9) . . ? C10 N1 C11 127.64(15) . . ? C10 N1 C13 117.30(14) . . ? C11 N1 C13 115.01(15) . . ? C34 N2 C35 127.83(15) . . ? C34 N2 C37 116.80(14) . . ? C35 N2 C37 115.27(15) . . ? C12 C1 C2 119.54(17) 2_666 . ? C12 C1 H1A 120.2 2_666 . ? C2 C1 H1A 120.2 . . ? C3 C2 C1 116.47(16) . . ? C3 C2 S1 108.24(13) . . ? C1 C2 S1 135.28(14) . . ? C2 C3 C9 124.12(17) . 2_666 ? C2 C3 C4 115.39(16) . . ? C9 C3 C4 120.48(17) 2_666 . ? C5 C4 C9 123.98(17) . . ? C5 C4 C3 114.97(17) . . ? C9 C4 C3 121.05(16) . . ? C4 C5 C6 116.23(17) . . ? C4 C5 S1 108.42(13) . . ? C6 C5 S1 135.35(14) . . ? C7 C6 C5 119.94(16) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C8 122.51(16) . . ? C6 C7 C10 121.22(16) . . ? C8 C7 C10 116.25(16) . . ? C9 C8 C12 116.61(15) . . ? C9 C8 C7 116.34(16) . . ? C12 C8 C7 127.04(16) . . ? C8 C9 C4 120.98(16) . . ? C8 C9 C3 120.54(17) . 2_666 ? C4 C9 C3 118.47(16) . 2_666 ? O1 C10 N1 119.38(17) . . ? O1 C10 C7 124.39(17) . . ? N1 C10 C7 116.20(15) . . ? O2 C11 N1 119.46(16) . . ? O2 C11 C12 124.72(16) . . ? N1 C11 C12 115.81(16) . . ? C1 C12 C8 122.72(16) 2_666 . ? C1 C12 C11 120.39(16) 2_666 . ? C8 C12 C11 116.80(15) . . ? C14 C13 C18 122.93(17) . . ? C14 C13 N1 119.30(16) . . ? C18 C13 N1 117.74(16) . . ? C15 C14 C13 117.10(18) . . ? C15 C14 C22 121.02(17) . . ? C13 C14 C22 121.82(17) . . ? C16 C15 C14 121.33(19) . . ? C16 C15 H15A 119.3 . . ? C14 C15 H15A 119.3 . . ? C17 C16 C15 120.00(19) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 121.15(18) . . ? C16 C17 H17A 119.4 . . ? C18 C17 H17A 119.4 . . ? C17 C18 C13 117.40(18) . . ? C17 C18 C19 120.83(17) . . ? C13 C18 C19 121.77(18) . . ? C18 C19 C21 111.17(17) . . ? C18 C19 C20 112.58(19) . . ? C21 C19 C20 110.44(19) . . ? C18 C19 H19A 107.5 . . ? C21 C19 H19A 107.5 . . ? C20 C19 H19A 107.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C14 113.07(18) . . ? C23 C22 C24 110.80(19) . . ? C14 C22 C24 110.58(17) . . ? C23 C22 H22A 107.4 . . ? C14 C22 H22A 107.4 . . ? C24 C22 H22A 107.4 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C36 C25 C26 119.19(17) 2_777 . ? C36 C25 H25A 120.4 2_777 . ? C26 C25 H25A 120.4 . . ? C27 C26 C25 116.93(16) . . ? C27 C26 S2 107.90(14) . . ? C25 C26 S2 135.16(15) . . ? C26 C27 C33 124.01(17) . 2_777 ? C26 C27 C28 115.60(16) . . ? C33 C27 C28 120.37(17) 2_777 . ? C33 C28 C29 123.68(17) . . ? C33 C28 C27 121.07(16) . . ? C29 C28 C27 115.26(17) . . ? C28 C29 C30 116.60(17) . . ? C28 C29 S2 108.09(14) . . ? C30 C29 S2 135.31(14) . . ? C31 C30 C29 119.88(16) . . ? C31 C30 H30A 120.1 . . ? C29 C30 H30A 120.1 . . ? C30 C31 C32 122.69(16) . . ? C30 C31 C34 120.93(15) . . ? C32 C31 C34 116.38(16) . . ? C33 C32 C36 116.60(16) . . ? C33 C32 C31 116.15(17) . . ? C36 C32 C31 127.24(17) . . ? C28 C33 C32 121.00(16) . . ? C28 C33 C27 118.55(16) . 2_777 ? C32 C33 C27 120.45(17) . 2_777 ? O3 C34 N2 119.61(17) . . ? O3 C34 C31 124.38(18) . . ? N2 C34 C31 115.99(15) . . ? O4 C35 N2 119.63(17) . . ? O4 C35 C36 124.39(16) . . ? N2 C35 C36 115.96(16) . . ? C25 C36 C32 122.81(16) 2_777 . ? C25 C36 C35 120.66(17) 2_777 . ? C32 C36 C35 116.51(15) . . ? C38 C37 C42 122.57(17) . . ? C38 C37 N2 119.51(16) . . ? C42 C37 N2 117.91(16) . . ? C39 C38 C37 117.20(17) . . ? C39 C38 C46 121.05(17) . . ? C37 C38 C46 121.75(17) . . ? C40 C39 C38 121.58(19) . . ? C40 C39 H39A 119.2 . . ? C38 C39 H39A 119.2 . . ? C41 C40 C39 119.83(19) . . ? C41 C40 H40A 120.1 . . ? C39 C40 H40A 120.1 . . ? C40 C41 C42 121.22(18) . . ? C40 C41 H41A 119.4 . . ? C42 C41 H41A 119.4 . . ? C41 C42 C37 117.57(17) . . ? C41 C42 C43 120.51(17) . . ? C37 C42 C43 121.92(17) . . ? C42 C43 C45 111.02(17) . . ? C42 C43 C44 111.14(17) . . ? C45 C43 C44 111.35(18) . . ? C42 C43 H43A 107.7 . . ? C45 C43 H43A 107.7 . . ? C44 C43 H43A 107.7 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C48 C46 C47 111.5(2) . . ? C48 C46 C38 112.24(18) . . ? C47 C46 C38 111.2(2) . . ? C48 C46 H46A 107.2 . . ? C47 C46 H46A 107.2 . . ? C38 C46 H46A 107.2 . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C46 C48 H48A 109.5 . . ? C46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C62 C49 C50 120.6(3) . . ? C62 C49 H49A 119.7 . . ? C50 C49 H49A 119.7 . . ? C49 C50 C51 121.0(3) . . ? C49 C50 H50A 119.5 . . ? C51 C50 H50A 119.5 . . ? C50 C51 C52 123.2(2) . . ? C50 C51 C63 118.3(3) . . ? C52 C51 C63 118.6(2) . . ? C53 C52 C51 121.9(2) . . ? C53 C52 H52A 119.1 . . ? C51 C52 H52A 119.1 . . ? C52 C53 C54 120.8(2) . . ? C52 C53 H53A 119.6 . . ? C54 C53 H53A 119.6 . . ? C55 C54 C64 118.5(2) . . ? C55 C54 C53 122.8(2) . . ? C64 C54 C53 118.7(2) . . ? C56 C55 C54 120.9(2) . . ? C56 C55 H55A 119.5 . . ? C54 C55 H55A 119.5 . . ? C55 C56 C57 120.8(2) . . ? C55 C56 H56A 119.6 . . ? C57 C56 H56A 119.6 . . ? C56 C57 C58 120.4(2) . . ? C56 C57 H57A 119.8 . . ? C58 C57 H57A 119.8 . . ? C57 C58 C64 119.0(2) . . ? C57 C58 C59 122.5(2) . . ? C64 C58 C59 118.5(2) . . ? C60 C59 C58 121.8(2) . . ? C60 C59 H59A 119.1 . . ? C58 C59 H59A 119.1 . . ? C59 C60 C61 121.7(2) . . ? C59 C60 H60A 119.2 . . ? C61 C60 H60A 119.2 . . ? C62 C61 C63 119.7(3) . . ? C62 C61 C60 122.1(3) . . ? C63 C61 C60 118.2(2) . . ? C49 C62 C61 120.8(3) . . ? C49 C62 H62A 119.6 . . ? C61 C62 H62A 119.6 . . ? C61 C63 C51 119.7(2) . . ? C61 C63 C64 120.4(2) . . ? C51 C63 C64 119.8(2) . . ? C54 C64 C58 120.4(2) . . ? C54 C64 C63 120.2(2) . . ? C58 C64 C63 119.4(2) . . ? C66 C65 C78 120.4(2) . . ? C66 C65 H65A 119.8 . . ? C78 C65 H65A 119.8 . . ? C65 C66 C67 121.1(2) . . ? C65 C66 H66A 119.4 . . ? C67 C66 H66A 119.4 . . ? C66 C67 C79 119.1(2) . . ? C66 C67 C68 122.7(2) . . ? C79 C67 C68 118.2(2) . . ? C69 C68 C67 121.1(2) . . ? C69 C68 H68A 119.5 . . ? C67 C68 H68A 119.5 . . ? C68 C69 C70 121.7(2) . . ? C68 C69 H69A 119.2 . . ? C70 C69 H69A 119.2 . . ? C71 C70 C69 122.5(2) . . ? C71 C70 C80 118.7(2) . . ? C69 C70 C80 118.8(2) . . ? C70 C71 C72 121.4(2) . . ? C70 C71 H71A 119.3 . . ? C72 C71 H71A 119.3 . . ? C73 C72 C71 120.2(2) . . ? C73 C72 H72A 119.9 . . ? C71 C72 H72A 119.9 . . ? C72 C73 C74 120.9(2) . . ? C72 C73 H73A 119.5 . . ? C74 C73 H73A 119.5 . . ? C73 C74 C80 119.0(2) . . ? C73 C74 C75 122.8(2) . . ? C80 C74 C75 118.2(2) . . ? C76 C75 C74 121.7(2) . . ? C76 C75 H75A 119.1 . . ? C74 C75 H75A 119.1 . . ? C75 C76 C77 121.4(2) . . ? C75 C76 H76A 119.3 . . ? C77 C76 H76A 119.3 . . ? C78 C77 C79 119.1(2) . . ? C78 C77 C76 122.9(2) . . ? C79 C77 C76 118.0(2) . . ? C77 C78 C65 120.9(3) . . ? C77 C78 H78A 119.5 . . ? C65 C78 H78A 119.5 . . ? C67 C79 C80 121.3(2) . . ? C67 C79 C77 119.3(2) . . ? C80 C79 C77 119.3(2) . . ? C74 C80 C79 121.3(2) . . ? C74 C80 C70 119.8(2) . . ? C79 C80 C70 119.0(2) . . ? Cl1 C81 Cl2 111.69(15) . . ? Cl1 C81 H81A 109.3 . . ? Cl2 C81 H81A 109.3 . . ? Cl1 C81 H81B 109.3 . . ? Cl2 C81 H81B 109.3 . . ? H81A C81 H81B 107.9 . . ? Cl6 C83 Cl5 111.95(15) . . ? Cl6 C83 H83A 109.2 . . ? Cl5 C83 H83A 109.2 . . ? Cl6 C83 H83B 109.2 . . ? Cl5 C83 H83B 109.2 . . ? H83A C83 H83B 107.9 . . ? Cl4 C82 Cl3 117.3(4) . . ? Cl4 C82 H82A 108.0 . . ? Cl3 C82 H82A 108.0 . . ? Cl4 C82 H82B 108.0 . . ? Cl3 C82 H82B 108.0 . . ? H82A C82 H82B 107.2 . . ? Cl4' C82' Cl3' 103.9(7) . . ? Cl4' C82' H82C 111.0 . . ? Cl3' C82' H82C 111.0 . . ? Cl4' C82' H82D 111.0 . . ? Cl3' C82' H82D 111.0 . . ? H82C C82' H82D 109.0 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 C1 C2 C3 0.0(2) 2_666 . . . ? C12 C1 C2 S1 -178.71(14) 2_666 . . . ? C5 S1 C2 C3 0.80(14) . . . . ? C5 S1 C2 C1 179.57(19) . . . . ? C1 C2 C3 C9 0.4(3) . . . 2_666 ? S1 C2 C3 C9 179.47(14) . . . 2_666 ? C1 C2 C3 C4 -179.33(16) . . . . ? S1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C9 C3 C4 C5 179.65(16) 2_666 . . . ? C2 C3 C4 C9 179.20(16) . . . . ? C9 C3 C4 C9 -0.6(3) 2_666 . . . ? C9 C4 C5 C6 1.3(3) . . . . ? C3 C4 C5 C6 -178.90(16) . . . . ? C9 C4 C5 S1 -178.62(15) . . . . ? C3 C4 C5 S1 1.1(2) . . . . ? C2 S1 C5 C4 -1.10(14) . . . . ? C2 S1 C5 C6 178.96(19) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? S1 C5 C6 C7 179.49(15) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 C10 178.16(16) . . . . ? C6 C7 C8 C9 0.6(2) . . . . ? C10 C7 C8 C9 -178.09(15) . . . . ? C6 C7 C8 C12 179.73(17) . . . . ? C10 C7 C8 C12 1.0(3) . . . . ? C12 C8 C9 C4 -178.99(16) . . . . ? C7 C8 C9 C4 0.2(2) . . . . ? C12 C8 C9 C3 -0.6(2) . . . 2_666 ? C7 C8 C9 C3 178.61(16) . . . 2_666 ? C5 C4 C9 C8 -1.2(3) . . . . ? C3 C4 C9 C8 179.01(16) . . . . ? C5 C4 C9 C3 -179.68(17) . . . 2_666 ? C3 C4 C9 C3 0.6(3) . . . 2_666 ? C11 N1 C10 O1 175.37(16) . . . . ? C13 N1 C10 O1 -7.4(2) . . . . ? C11 N1 C10 C7 -6.2(3) . . . . ? C13 N1 C10 C7 171.00(15) . . . . ? C6 C7 C10 O1 2.5(3) . . . . ? C8 C7 C10 O1 -178.70(16) . . . . ? C6 C7 C10 N1 -175.76(15) . . . . ? C8 C7 C10 N1 3.0(2) . . . . ? C10 N1 C11 O2 -176.36(17) . . . . ? C13 N1 C11 O2 6.4(2) . . . . ? C10 N1 C11 C12 4.9(2) . . . . ? C13 N1 C11 C12 -172.37(15) . . . . ? C9 C8 C12 C1 0.2(2) . . . 2_666 ? C7 C8 C12 C1 -178.91(16) . . . 2_666 ? C9 C8 C12 C11 176.77(15) . . . . ? C7 C8 C12 C11 -2.3(3) . . . . ? O2 C11 C12 C1 -2.4(3) . . . 2_666 ? N1 C11 C12 C1 176.24(15) . . . 2_666 ? O2 C11 C12 C8 -179.10(17) . . . . ? N1 C11 C12 C8 -0.4(2) . . . . ? C10 N1 C13 C14 95.2(2) . . . . ? C11 N1 C13 C14 -87.2(2) . . . . ? C10 N1 C13 C18 -86.6(2) . . . . ? C11 N1 C13 C18 90.95(19) . . . . ? C18 C13 C14 C15 -3.2(3) . . . . ? N1 C13 C14 C15 174.89(17) . . . . ? C18 C13 C14 C22 174.01(18) . . . . ? N1 C13 C14 C22 -7.9(3) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C22 C14 C15 C16 -176.27(19) . . . . ? C14 C15 C16 C17 1.3(3) . . . . ? C15 C16 C17 C18 -1.5(3) . . . . ? C16 C17 C18 C13 -0.6(3) . . . . ? C16 C17 C18 C19 179.83(19) . . . . ? C14 C13 C18 C17 3.0(3) . . . . ? N1 C13 C18 C17 -175.08(17) . . . . ? C14 C13 C18 C19 -177.41(18) . . . . ? N1 C13 C18 C19 4.5(3) . . . . ? C17 C18 C19 C21 74.5(2) . . . . ? C13 C18 C19 C21 -105.1(2) . . . . ? C17 C18 C19 C20 -50.0(3) . . . . ? C13 C18 C19 C20 130.4(2) . . . . ? C15 C14 C22 C23 -58.2(3) . . . . ? C13 C14 C22 C23 124.7(2) . . . . ? C15 C14 C22 C24 66.7(3) . . . . ? C13 C14 C22 C24 -110.4(2) . . . . ? C36 C25 C26 C27 -0.5(3) 2_777 . . . ? C36 C25 C26 S2 -179.74(15) 2_777 . . . ? C29 S2 C26 C27 -0.54(14) . . . . ? C29 S2 C26 C25 178.7(2) . . . . ? C25 C26 C27 C33 0.0(3) . . . 2_777 ? S2 C26 C27 C33 179.46(15) . . . 2_777 ? C25 C26 C27 C28 -178.56(16) . . . . ? S2 C26 C27 C28 0.9(2) . . . . ? C26 C27 C28 C33 179.53(16) . . . . ? C33 C27 C28 C33 0.9(3) 2_777 . . . ? C26 C27 C28 C29 -0.8(2) . . . . ? C33 C27 C28 C29 -179.50(16) 2_777 . . . ? C33 C28 C29 C30 -0.1(3) . . . . ? C27 C28 C29 C30 -179.68(16) . . . . ? C33 C28 C29 S2 179.99(14) . . . . ? C27 C28 C29 S2 0.4(2) . . . . ? C26 S2 C29 C28 0.10(14) . . . . ? C26 S2 C29 C30 -179.8(2) . . . . ? C28 C29 C30 C31 0.7(3) . . . . ? S2 C29 C30 C31 -179.40(15) . . . . ? C29 C30 C31 C32 -1.0(3) . . . . ? C29 C30 C31 C34 178.36(16) . . . . ? C30 C31 C32 C33 0.6(3) . . . . ? C34 C31 C32 C33 -178.73(16) . . . . ? C30 C31 C32 C36 179.63(17) . . . . ? C34 C31 C32 C36 0.3(3) . . . . ? C29 C28 C33 C32 -0.3(3) . . . . ? C27 C28 C33 C32 179.33(16) . . . . ? C29 C28 C33 C27 179.55(17) . . . 2_777 ? C27 C28 C33 C27 -0.9(3) . . . 2_777 ? C36 C32 C33 C28 -179.12(16) . . . . ? C31 C32 C33 C28 0.0(3) . . . . ? C36 C32 C33 C27 1.1(3) . . . 2_777 ? C31 C32 C33 C27 -179.83(16) . . . 2_777 ? C35 N2 C34 O3 177.89(17) . . . . ? C37 N2 C34 O3 -6.0(2) . . . . ? C35 N2 C34 C31 -3.6(3) . . . . ? C37 N2 C34 C31 172.51(15) . . . . ? C30 C31 C34 O3 1.0(3) . . . . ? C32 C31 C34 O3 -179.65(18) . . . . ? C30 C31 C34 N2 -177.46(15) . . . . ? C32 C31 C34 N2 1.9(2) . . . . ? C34 N2 C35 O4 -178.72(17) . . . . ? C37 N2 C35 O4 5.1(2) . . . . ? C34 N2 C35 C36 2.7(3) . . . . ? C37 N2 C35 C36 -173.43(15) . . . . ? C33 C32 C36 C25 -0.6(3) . . . 2_777 ? C31 C32 C36 C25 -179.58(17) . . . 2_777 ? C33 C32 C36 C35 177.84(15) . . . . ? C31 C32 C36 C35 -1.1(3) . . . . ? O4 C35 C36 C25 -0.2(3) . . . 2_777 ? N2 C35 C36 C25 178.24(15) . . . 2_777 ? O4 C35 C36 C32 -178.72(17) . . . . ? N2 C35 C36 C32 -0.2(2) . . . . ? C34 N2 C37 C38 98.6(2) . . . . ? C35 N2 C37 C38 -84.8(2) . . . . ? C34 N2 C37 C42 -82.5(2) . . . . ? C35 N2 C37 C42 94.08(19) . . . . ? C42 C37 C38 C39 -1.5(3) . . . . ? N2 C37 C38 C39 177.30(17) . . . . ? C42 C37 C38 C46 178.52(18) . . . . ? N2 C37 C38 C46 -2.7(3) . . . . ? C37 C38 C39 C40 -0.1(3) . . . . ? C46 C38 C39 C40 179.88(19) . . . . ? C38 C39 C40 C41 1.2(3) . . . . ? C39 C40 C41 C42 -0.7(3) . . . . ? C40 C41 C42 C37 -0.8(3) . . . . ? C40 C41 C42 C43 179.76(18) . . . . ? C38 C37 C42 C41 1.9(3) . . . . ? N2 C37 C42 C41 -176.87(16) . . . . ? C38 C37 C42 C43 -178.62(17) . . . . ? N2 C37 C42 C43 2.6(3) . . . . ? C41 C42 C43 C45 62.9(2) . . . . ? C37 C42 C43 C45 -116.5(2) . . . . ? C41 C42 C43 C44 -61.6(3) . . . . ? C37 C42 C43 C44 119.0(2) . . . . ? C39 C38 C46 C48 60.9(3) . . . . ? C37 C38 C46 C48 -119.1(2) . . . . ? C39 C38 C46 C47 -64.8(3) . . . . ? C37 C38 C46 C47 115.2(3) . . . . ? C62 C49 C50 C51 0.3(4) . . . . ? C49 C50 C51 C52 179.1(2) . . . . ? C49 C50 C51 C63 -0.5(3) . . . . ? C50 C51 C52 C53 179.9(2) . . . . ? C63 C51 C52 C53 -0.5(3) . . . . ? C51 C52 C53 C54 -0.6(3) . . . . ? C52 C53 C54 C55 -179.2(2) . . . . ? C52 C53 C54 C64 1.7(3) . . . . ? C64 C54 C55 C56 0.1(3) . . . . ? C53 C54 C55 C56 -179.0(2) . . . . ? C54 C55 C56 C57 0.3(3) . . . . ? C55 C56 C57 C58 -0.7(3) . . . . ? C56 C57 C58 C64 0.6(3) . . . . ? C56 C57 C58 C59 179.9(2) . . . . ? C57 C58 C59 C60 179.8(2) . . . . ? C64 C58 C59 C60 -0.9(3) . . . . ? C58 C59 C60 C61 -0.3(3) . . . . ? C59 C60 C61 C62 -179.8(2) . . . . ? C59 C60 C61 C63 1.1(3) . . . . ? C50 C49 C62 C61 -0.2(4) . . . . ? C63 C61 C62 C49 0.2(3) . . . . ? C60 C61 C62 C49 -178.9(2) . . . . ? C62 C61 C63 C51 -0.4(3) . . . . ? C60 C61 C63 C51 178.78(19) . . . . ? C62 C61 C63 C64 -179.81(19) . . . . ? C60 C61 C63 C64 -0.6(3) . . . . ? C50 C51 C63 C61 0.5(3) . . . . ? C52 C51 C63 C61 -179.09(19) . . . . ? C50 C51 C63 C64 179.96(18) . . . . ? C52 C51 C63 C64 0.3(3) . . . . ? C55 C54 C64 C58 -0.1(3) . . . . ? C53 C54 C64 C58 178.95(18) . . . . ? C55 C54 C64 C63 179.08(18) . . . . ? C53 C54 C64 C63 -1.8(3) . . . . ? C57 C58 C64 C54 -0.2(3) . . . . ? C59 C58 C64 C54 -179.51(18) . . . . ? C57 C58 C64 C63 -179.42(18) . . . . ? C59 C58 C64 C63 1.3(3) . . . . ? C61 C63 C64 C54 -179.76(18) . . . . ? C51 C63 C64 C54 0.8(3) . . . . ? C61 C63 C64 C58 -0.5(3) . . . . ? C51 C63 C64 C58 -179.93(18) . . . . ? C78 C65 C66 C67 0.3(4) . . . . ? C65 C66 C67 C79 0.0(3) . . . . ? C65 C66 C67 C68 179.8(2) . . . . ? C66 C67 C68 C69 -179.7(2) . . . . ? C79 C67 C68 C69 0.2(3) . . . . ? C67 C68 C69 C70 0.0(3) . . . . ? C68 C69 C70 C71 -179.9(2) . . . . ? C68 C69 C70 C80 -0.3(3) . . . . ? C69 C70 C71 C72 -179.4(2) . . . . ? C80 C70 C71 C72 1.0(3) . . . . ? C70 C71 C72 C73 -0.5(3) . . . . ? C71 C72 C73 C74 -0.3(3) . . . . ? C72 C73 C74 C80 0.5(3) . . . . ? C72 C73 C74 C75 -179.3(2) . . . . ? C73 C74 C75 C76 -179.4(2) . . . . ? C80 C74 C75 C76 0.8(3) . . . . ? C74 C75 C76 C77 -0.2(3) . . . . ? C75 C76 C77 C78 179.7(2) . . . . ? C75 C76 C77 C79 -0.3(3) . . . . ? C79 C77 C78 C65 0.1(3) . . . . ? C76 C77 C78 C65 -179.8(2) . . . . ? C66 C65 C78 C77 -0.4(4) . . . . ? C66 C67 C79 C80 179.80(18) . . . . ? C68 C67 C79 C80 0.0(3) . . . . ? C66 C67 C79 C77 -0.2(3) . . . . ? C68 C67 C79 C77 179.98(18) . . . . ? C78 C77 C79 C67 0.1(3) . . . . ? C76 C77 C79 C67 -179.89(18) . . . . ? C78 C77 C79 C80 -179.85(19) . . . . ? C76 C77 C79 C80 0.1(3) . . . . ? C73 C74 C80 C79 179.22(18) . . . . ? C75 C74 C80 C79 -0.9(3) . . . . ? C73 C74 C80 C70 -0.1(3) . . . . ? C75 C74 C80 C70 179.82(18) . . . . ? C67 C79 C80 C74 -179.53(18) . . . . ? C77 C79 C80 C74 0.5(3) . . . . ? C67 C79 C80 C70 -0.2(3) . . . . ? C77 C79 C80 C70 179.76(18) . . . . ? C71 C70 C80 C74 -0.7(3) . . . . ? C69 C70 C80 C74 179.69(18) . . . . ? C71 C70 C80 C79 -179.97(18) . . . . ? C69 C70 C80 C79 0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.449 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.076