# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl _database_code_depnum_ccdc_archive 'CCDC 898519' #TrackingRef 'jmd53_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C37 H34 N2 O2 S2), C Cl4' _chemical_formula_sum 'C112 H102 Cl4 N6 O6 S6' _chemical_formula_weight 1962.16 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 trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 23.896(7) _cell_length_b 23.896(7) _cell_length_c 30.268(9) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 120.0 _cell_volume 14968(8) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4397 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 24.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6168 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.628 _exptl_absorpt_correction_T_max 0.745 _exptl_absorpt_process_details 'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19836 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5877 _reflns_number_gt 3146 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The refinement showed a disordered CCl4 molecule in the structure with C and one Cl atom lying on the three fold axis with a site occupany of 0.3333. The disorder in other Cl atom was resolved by splitting it in two positions and refining anisotropically with restraints on C-Cl bonding and Cl...Cl non-bonding distances. The hydrogens of the -OH groups were located from the difference Fourier synthesis and were refined isotropically with uiso values 1.2 times that of their carrier oxygen atoms, with restraints on the O-H distance. 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^)+(0.1555P)^2^+9.4232P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5877 _refine_ls_number_parameters 417 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1260 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.2613 _refine_ls_wR_factor_gt 0.2042 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.998 _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 C1 C 0.66096(17) 0.02738(17) 0.41058(13) 0.0690(10) Uani 1 1 d . . . C2 C 0.63304(17) 0.06645(16) 0.41378(12) 0.0633(9) Uani 1 1 d . . . C3 C 0.5986(2) 0.06435(18) 0.45162(14) 0.0759(11) Uani 1 1 d . . . C4 C 0.5940(2) 0.0241(2) 0.48611(14) 0.0843(12) Uani 1 1 d . . . H4 H 0.5710 0.0227 0.5113 0.101 Uiso 1 1 calc R . . C5 C 0.6223(2) -0.0140(2) 0.48437(16) 0.0855(13) Uani 1 1 d . . . C6 C 0.65611(19) -0.01296(18) 0.44616(16) 0.0769(11) Uani 1 1 d . . . C7 C 0.64108(19) 0.11205(17) 0.37714(12) 0.0706(10) Uani 1 1 d . . . H7A H 0.6840 0.1301 0.3645 0.085 Uiso 1 1 calc R . . H7B H 0.6363 0.1473 0.3887 0.085 Uiso 1 1 calc R . . C8 C 0.60145(18) 0.12924(19) 0.29357(12) 0.0678(10) Uani 1 1 d . . . C9 C 0.64792(19) 0.1937(2) 0.29902(15) 0.0797(11) Uani 1 1 d . . . H9 H 0.6706 0.2072 0.3255 0.096 Uiso 1 1 calc R . . C10 C 0.6608(2) 0.2374(2) 0.26648(19) 0.0908(14) Uani 1 1 d . . . H10 H 0.6919 0.2804 0.2710 0.109 Uiso 1 1 calc R . . C11 C 0.6292(3) 0.2193(3) 0.2278(2) 0.1049(17) Uani 1 1 d . . . H11 H 0.6388 0.2499 0.2058 0.126 Uiso 1 1 calc R . . C12 C 0.5829(3) 0.1559(3) 0.22045(15) 0.0953(14) Uani 1 1 d . . . H12 H 0.5610 0.1438 0.1936 0.114 Uiso 1 1 calc R . . C13 C 0.56874(19) 0.1098(2) 0.25354(12) 0.0700(10) Uani 1 1 d . . . C14 C 0.4897(2) 0.0181(3) 0.21441(14) 0.0858(13) Uani 1 1 d . . . H14 H 0.4943 0.0453 0.1910 0.103 Uiso 1 1 calc R . . C15 C 0.4450(2) -0.0500(3) 0.20989(15) 0.0874(13) Uani 1 1 d . . . C16 C 0.4341(2) -0.0933(3) 0.24389(18) 0.0962(14) Uani 1 1 d . . . C17 C 0.3904(3) -0.1583(3) 0.2389(2) 0.129(2) Uani 1 1 d . . . H17 H 0.3828 -0.1873 0.2617 0.155 Uiso 1 1 calc R . . C18 C 0.3579(3) -0.1791(4) 0.1987(3) 0.149(3) Uani 1 1 d . . . H18 H 0.3292 -0.2230 0.1949 0.179 Uiso 1 1 calc R . . C19 C 0.3657(4) -0.1398(5) 0.1656(3) 0.149(3) Uani 1 1 d . . . H19 H 0.3421 -0.1554 0.1396 0.178 Uiso 1 1 calc R . . C20 C 0.4097(3) -0.0747(4) 0.17066(18) 0.127(2) Uani 1 1 d . . . H20 H 0.4161 -0.0466 0.1475 0.153 Uiso 1 1 calc R . . C21 C 0.6876(2) -0.0537(2) 0.44350(19) 0.0970(14) Uani 1 1 d . . . H21A H 0.6962 -0.0634 0.4730 0.116 Uiso 1 1 calc R . . H21B H 0.7284 -0.0304 0.4279 0.116 Uiso 1 1 calc R . . C22 C 0.6876(2) -0.1551(2) 0.39686(19) 0.0995(15) Uani 1 1 d . . . C23 C 0.7495(3) -0.1121(3) 0.3817(3) 0.139(2) Uani 1 1 d . . . H23 H 0.7638 -0.0680 0.3811 0.167 Uiso 1 1 calc R . . C24 C 0.7897(3) -0.1340(4) 0.3677(3) 0.161(3) Uani 1 1 d . . . H24 H 0.8300 -0.1050 0.3561 0.193 Uiso 1 1 calc R . . C25 C 0.7710(4) -0.1981(4) 0.3705(3) 0.149(3) Uani 1 1 d . . . H25 H 0.7998 -0.2121 0.3634 0.178 Uiso 1 1 calc R . . C26 C 0.7107(3) -0.2405(3) 0.3837(2) 0.122(2) Uani 1 1 d . . . H26 H 0.6979 -0.2842 0.3846 0.146 Uiso 1 1 calc R . . C27 C 0.6661(3) -0.2210(2) 0.39631(16) 0.0933(14) Uani 1 1 d . . . C28 C 0.5712(3) -0.3231(2) 0.39755(16) 0.1000(15) Uani 1 1 d . . . H28 H 0.5925 -0.3379 0.3794 0.120 Uiso 1 1 calc R . . C29 C 0.5063(3) -0.3674(2) 0.41021(15) 0.0950(14) Uani 1 1 d . . . C30 C 0.4707(3) -0.3480(3) 0.43554(17) 0.1078(16) Uani 1 1 d . . . C31 C 0.4065(4) -0.3925(4) 0.4463(2) 0.141(2) Uani 1 1 d . . . H31 H 0.3820 -0.3799 0.4630 0.169 Uiso 1 1 calc R . . C32 C 0.3801(4) -0.4557(3) 0.4314(3) 0.148(2) Uani 1 1 d . . . H32 H 0.3370 -0.4850 0.4375 0.178 Uiso 1 1 calc R . . C33 C 0.4151(4) -0.4762(3) 0.4085(2) 0.138(2) Uani 1 1 d . . . H33 H 0.3974 -0.5194 0.4007 0.166 Uiso 1 1 calc R . . C34 C 0.4772(3) -0.4315(3) 0.39710(19) 0.1219(19) Uani 1 1 d . . . H34 H 0.5007 -0.4447 0.3799 0.146 Uiso 1 1 calc R . . C35 C 0.6963(2) 0.0286(2) 0.36984(16) 0.0932(13) Uani 1 1 d . . . H35A H 0.6842 0.0470 0.3460 0.140 Uiso 1 1 calc R . . H35B H 0.6856 -0.0146 0.3623 0.140 Uiso 1 1 calc R . . H35C H 0.7420 0.0543 0.3749 0.140 Uiso 1 1 calc R . . C36 C 0.5671(3) 0.1049(2) 0.45610(18) 0.1069(16) Uani 1 1 d . . . H36A H 0.5432 0.0944 0.4832 0.160 Uiso 1 1 calc R . . H36B H 0.5384 0.0965 0.4317 0.160 Uiso 1 1 calc R . . H36C H 0.5997 0.1498 0.4562 0.160 Uiso 1 1 calc R . . C37 C 0.6144(3) -0.0578(3) 0.5229(2) 0.132(2) Uani 1 1 d . . . H37A H 0.5891 -0.0529 0.5456 0.198 Uiso 1 1 calc R . . H37B H 0.6562 -0.0464 0.5346 0.198 Uiso 1 1 calc R . . H37C H 0.5931 -0.1019 0.5131 0.198 Uiso 1 1 calc R . . N1 N 0.52313(16) 0.04239(17) 0.24906(10) 0.0729(9) Uani 1 1 d . . . N2 N 0.6019(2) -0.26344(18) 0.41008(12) 0.0879(10) Uani 1 1 d . . . O1 O 0.4649(2) -0.07371(16) 0.28309(12) 0.1130(11) Uani 1 1 d D . . H1 H 0.495(2) -0.0337(13) 0.281(2) 0.136 Uiso 1 1 d D . . O2 O 0.4964(2) -0.2857(2) 0.44980(14) 0.1353(14) Uani 1 1 d D . . H2 H 0.5359(15) -0.263(3) 0.440(2) 0.162 Uiso 1 1 d D . . S1 S 0.58057(5) 0.06928(5) 0.33458(4) 0.0859(4) Uani 1 1 d . . . S2 S 0.63383(6) -0.12892(6) 0.41432(6) 0.1127(6) Uani 1 1 d . . . C38 C 0.3333 0.6667 0.3215(5) 0.257(9) Uani 1 3 d SD . . Cl1 Cl 0.3333 0.6667 0.27000(15) 0.1998(17) Uani 1 3 d SD A . Cl2 Cl 0.3764(6) 0.6361(5) 0.3468(2) 0.427(6) Uani 0.849(10) 1 d PD A 1 Cl2' Cl 0.303(3) 0.713(3) 0.3419(8) 0.427(6) Uani 0.151(10) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.058(2) 0.055(2) 0.080(3) -0.0126(19) -0.0116(19) 0.0181(18) C2 0.062(2) 0.0490(19) 0.070(2) -0.0040(17) -0.0091(18) 0.0214(17) C3 0.083(3) 0.056(2) 0.084(3) 0.003(2) -0.004(2) 0.032(2) C4 0.093(3) 0.081(3) 0.076(3) 0.004(2) 0.002(2) 0.042(3) C5 0.083(3) 0.067(3) 0.094(3) 0.011(2) -0.015(3) 0.029(2) C6 0.063(2) 0.055(2) 0.107(3) -0.006(2) -0.023(2) 0.0246(19) C7 0.069(2) 0.055(2) 0.076(2) -0.0023(18) -0.0097(19) 0.0213(18) C8 0.064(2) 0.077(3) 0.070(2) 0.0178(19) 0.0130(19) 0.041(2) C9 0.067(2) 0.071(3) 0.095(3) 0.020(2) 0.012(2) 0.030(2) C10 0.077(3) 0.087(3) 0.118(4) 0.033(3) 0.029(3) 0.048(3) C11 0.120(4) 0.103(4) 0.117(4) 0.049(3) 0.050(4) 0.076(4) C12 0.118(4) 0.130(4) 0.071(3) 0.025(3) 0.021(3) 0.087(4) C13 0.068(2) 0.093(3) 0.069(2) 0.012(2) 0.018(2) 0.056(2) C14 0.071(3) 0.131(4) 0.065(3) 0.006(3) 0.009(2) 0.058(3) C15 0.072(3) 0.130(4) 0.076(3) -0.022(3) -0.005(2) 0.061(3) C16 0.099(3) 0.102(4) 0.107(4) -0.037(3) -0.030(3) 0.064(3) C17 0.119(4) 0.110(4) 0.163(6) -0.044(4) -0.033(4) 0.061(4) C18 0.107(5) 0.150(7) 0.199(8) -0.094(7) -0.049(6) 0.070(5) C19 0.116(5) 0.211(10) 0.135(6) -0.091(6) -0.046(5) 0.094(6) C20 0.101(4) 0.197(7) 0.087(3) -0.042(4) -0.026(3) 0.076(5) C21 0.079(3) 0.075(3) 0.138(4) -0.010(3) -0.025(3) 0.040(2) C22 0.078(3) 0.086(3) 0.139(4) -0.016(3) -0.026(3) 0.044(3) C23 0.077(4) 0.110(4) 0.227(7) -0.014(4) -0.001(4) 0.045(3) C24 0.094(4) 0.154(7) 0.233(8) -0.037(6) -0.016(5) 0.060(5) C25 0.097(5) 0.162(7) 0.205(7) -0.071(6) -0.033(4) 0.079(5) C26 0.128(5) 0.121(5) 0.147(5) -0.058(4) -0.045(4) 0.085(4) C27 0.098(3) 0.084(3) 0.108(3) -0.031(3) -0.038(3) 0.053(3) C28 0.132(4) 0.081(3) 0.088(3) -0.023(3) -0.006(3) 0.053(3) C29 0.116(4) 0.074(3) 0.078(3) -0.012(2) 0.003(3) 0.036(3) C30 0.140(5) 0.086(3) 0.089(3) -0.010(3) 0.012(3) 0.050(3) C31 0.161(6) 0.127(5) 0.117(5) 0.005(4) 0.037(4) 0.058(5) C32 0.144(6) 0.094(5) 0.163(6) 0.009(4) 0.024(5) 0.028(4) C33 0.160(7) 0.086(4) 0.143(5) -0.005(4) 0.009(5) 0.042(4) C34 0.152(5) 0.085(4) 0.111(4) -0.022(3) 0.003(4) 0.047(4) C35 0.082(3) 0.081(3) 0.110(3) -0.023(3) -0.007(3) 0.036(2) C36 0.125(4) 0.091(3) 0.122(4) 0.013(3) 0.028(3) 0.067(3) C37 0.135(5) 0.133(5) 0.130(5) 0.050(4) -0.006(4) 0.068(4) N1 0.072(2) 0.097(3) 0.0637(19) 0.0003(18) 0.0035(17) 0.053(2) N2 0.110(3) 0.072(2) 0.086(2) -0.0168(19) -0.019(2) 0.048(2) O1 0.136(3) 0.089(2) 0.111(2) -0.006(2) -0.035(2) 0.054(2) O2 0.164(4) 0.104(3) 0.130(3) -0.035(2) 0.020(3) 0.061(3) S1 0.0763(7) 0.0650(7) 0.0822(7) 0.0144(5) -0.0153(5) 0.0097(5) S2 0.0712(8) 0.0677(7) 0.2004(16) -0.0244(8) -0.0266(8) 0.0355(6) C38 0.262(16) 0.262(16) 0.25(2) 0.000 0.000 0.131(8) Cl1 0.222(3) 0.222(3) 0.155(3) 0.000 0.000 0.1111(14) Cl2 0.616(16) 0.338(9) 0.345(7) 0.021(5) -0.197(8) 0.252(9) Cl2' 0.616(16) 0.338(9) 0.345(7) 0.021(5) -0.197(8) 0.252(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 C1 C2 1.396(5) . ? C1 C6 1.411(6) . ? C1 C35 1.486(6) . ? C2 C3 1.396(5) . ? C2 C7 1.498(5) . ? C3 C4 1.386(6) . ? C3 C36 1.502(6) . ? C4 C5 1.381(6) . ? C4 H4 0.9300 . ? C5 C6 1.403(6) . ? C5 C37 1.516(6) . ? C6 C21 1.502(6) . ? C7 S1 1.821(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.387(5) . ? C8 C13 1.390(5) . ? C8 S1 1.769(4) . ? C9 C10 1.354(6) . ? C9 H9 0.9300 . ? C10 C11 1.341(7) . ? C10 H10 0.9300 . ? C11 C12 1.376(7) . ? C11 H11 0.9300 . ? C12 C13 1.401(6) . ? C12 H12 0.9300 . ? C13 N1 1.430(5) . ? C14 N1 1.269(5) . ? C14 C15 1.439(6) . ? C14 H14 0.9300 . ? C15 C16 1.389(7) . ? C15 C20 1.404(7) . ? C16 O1 1.350(6) . ? C16 C17 1.379(7) . ? C17 C18 1.397(9) . ? C17 H17 0.9300 . ? C18 C19 1.322(10) . ? C18 H18 0.9300 . ? C19 C20 1.382(10) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 S2 1.831(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C27 1.390(6) . ? C22 C23 1.391(7) . ? C22 S2 1.768(5) . ? C23 C24 1.370(9) . ? C23 H23 0.9300 . ? C24 C25 1.366(10) . ? C24 H24 0.9300 . ? C25 C26 1.343(9) . ? C25 H25 0.9300 . ? C26 C27 1.413(7) . ? C26 H26 0.9300 . ? C27 N2 1.414(6) . ? C28 N2 1.292(5) . ? C28 C29 1.425(7) . ? C28 H28 0.9300 . ? C29 C30 1.387(7) . ? C29 C34 1.387(7) . ? C30 O2 1.365(6) . ? C30 C31 1.400(8) . ? C31 C32 1.390(9) . ? C31 H31 0.9300 . ? C32 C33 1.352(9) . ? C32 H32 0.9300 . ? C33 C34 1.370(9) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? O1 H1 0.86(2) . ? O2 H2 0.87(6) . ? C38 Cl1 1.558(14) . ? C38 Cl2 1.712(3) 2_665 ? C38 Cl2 1.712(3) . ? C38 Cl2 1.712(3) 3_565 ? C38 Cl2' 1.724(3) 3_565 ? C38 Cl2' 1.724(3) 2_665 ? C38 Cl2' 1.724(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.0(4) . . ? C2 C1 C35 120.1(4) . . ? C6 C1 C35 119.9(4) . . ? C1 C2 C3 120.2(3) . . ? C1 C2 C7 120.3(4) . . ? C3 C2 C7 119.5(3) . . ? C4 C3 C2 119.0(4) . . ? C4 C3 C36 119.2(4) . . ? C2 C3 C36 121.8(4) . . ? C5 C4 C3 122.2(4) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 119.1(4) . . ? C4 C5 C37 119.6(5) . . ? C6 C5 C37 121.2(5) . . ? C5 C6 C1 119.4(4) . . ? C5 C6 C21 120.2(4) . . ? C1 C6 C21 120.4(4) . . ? C2 C7 S1 109.8(2) . . ? C2 C7 H7A 109.7 . . ? S1 C7 H7A 109.7 . . ? C2 C7 H7B 109.7 . . ? S1 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C13 118.7(4) . . ? C9 C8 S1 124.1(3) . . ? C13 C8 S1 117.2(3) . . ? C10 C9 C8 121.1(5) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C11 C10 C9 120.8(5) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.6(5) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 119.7(5) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C8 C13 C12 119.1(4) . . ? C8 C13 N1 116.4(3) . . ? C12 C13 N1 124.5(4) . . ? N1 C14 C15 122.5(4) . . ? N1 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? C16 C15 C20 117.7(5) . . ? C16 C15 C14 121.9(4) . . ? C20 C15 C14 120.4(5) . . ? O1 C16 C17 117.4(6) . . ? O1 C16 C15 121.8(5) . . ? C17 C16 C15 120.8(5) . . ? C16 C17 C18 118.0(7) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? C19 C18 C17 123.5(8) . . ? C19 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? C18 C19 C20 118.3(7) . . ? C18 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? C19 C20 C15 121.8(7) . . ? C19 C20 H20 119.1 . . ? C15 C20 H20 119.1 . . ? C6 C21 S2 109.2(3) . . ? C6 C21 H21A 109.8 . . ? S2 C21 H21A 109.8 . . ? C6 C21 H21B 109.8 . . ? S2 C21 H21B 109.8 . . ? H21A C21 H21B 108.3 . . ? C27 C22 C23 119.2(5) . . ? C27 C22 S2 118.8(4) . . ? C23 C22 S2 122.0(4) . . ? C24 C23 C22 120.6(6) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 120.7(7) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 119.4(6) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C27 122.2(6) . . ? C25 C26 H26 118.9 . . ? C27 C26 H26 118.9 . . ? C22 C27 C26 117.6(5) . . ? C22 C27 N2 117.6(4) . . ? C26 C27 N2 124.7(5) . . ? N2 C28 C29 123.1(5) . . ? N2 C28 H28 118.4 . . ? C29 C28 H28 118.4 . . ? C30 C29 C34 118.4(5) . . ? C30 C29 C28 121.5(4) . . ? C34 C29 C28 120.2(5) . . ? O2 C30 C29 121.5(5) . . ? O2 C30 C31 118.6(6) . . ? C29 C30 C31 119.8(5) . . ? C32 C31 C30 118.7(6) . . ? C32 C31 H31 120.7 . . ? C30 C31 H31 120.7 . . ? C33 C32 C31 122.3(7) . . ? C33 C32 H32 118.9 . . ? C31 C32 H32 118.9 . . ? C32 C33 C34 118.1(6) . . ? C32 C33 H33 120.9 . . ? C34 C33 H33 120.9 . . ? C33 C34 C29 122.6(6) . . ? C33 C34 H34 118.7 . . ? C29 C34 H34 118.7 . . ? C1 C35 H35A 109.5 . . ? C1 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C1 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C3 C36 H36A 109.5 . . ? C3 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C3 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C5 C37 H37A 109.5 . . ? C5 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C5 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C14 N1 C13 123.0(4) . . ? C28 N2 C27 121.2(4) . . ? C16 O1 H1 108(4) . . ? C30 O2 H2 109(5) . . ? C8 S1 C7 102.63(18) . . ? C22 S2 C21 102.3(2) . . ? Cl1 C38 Cl2 116.7(6) . 2_665 ? Cl1 C38 Cl2 116.7(6) . . ? Cl2 C38 Cl2 101.4(7) 2_665 . ? Cl1 C38 Cl2 116.7(6) . 3_565 ? Cl2 C38 Cl2 101.4(7) 2_665 3_565 ? Cl2 C38 Cl2 101.4(7) . 3_565 ? Cl1 C38 Cl2' 111.0(10) . 3_565 ? Cl2 C38 Cl2' 65.5(18) 2_665 3_565 ? Cl2 C38 Cl2' 130.8(13) 3_565 3_565 ? Cl1 C38 Cl2' 111.0(10) . 2_665 ? Cl2 C38 Cl2' 130.8(13) 2_665 2_665 ? Cl2 C38 Cl2' 65.5(18) . 2_665 ? Cl2' C38 Cl2' 107.9(10) 3_565 2_665 ? Cl1 C38 Cl2' 111.0(10) . . ? Cl2 C38 Cl2' 130.8(13) . . ? Cl2 C38 Cl2' 65.5(18) 3_565 . ? Cl2' C38 Cl2' 107.9(10) 3_565 . ? Cl2' C38 Cl2' 107.9(10) 2_665 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.9(5) . . . . ? C35 C1 C2 C3 178.6(3) . . . . ? C6 C1 C2 C7 176.7(3) . . . . ? C35 C1 C2 C7 -2.8(5) . . . . ? C1 C2 C3 C4 1.4(6) . . . . ? C7 C2 C3 C4 -177.1(3) . . . . ? C1 C2 C3 C36 -179.2(4) . . . . ? C7 C2 C3 C36 2.3(6) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? C36 C3 C4 C5 -179.3(4) . . . . ? C3 C4 C5 C6 -1.1(6) . . . . ? C3 C4 C5 C37 -178.9(4) . . . . ? C4 C5 C6 C1 0.7(6) . . . . ? C37 C5 C6 C1 178.4(4) . . . . ? C4 C5 C6 C21 179.7(4) . . . . ? C37 C5 C6 C21 -2.5(6) . . . . ? C2 C1 C6 C5 0.8(5) . . . . ? C35 C1 C6 C5 -179.7(4) . . . . ? C2 C1 C6 C21 -178.3(3) . . . . ? C35 C1 C6 C21 1.2(5) . . . . ? C1 C2 C7 S1 84.0(4) . . . . ? C3 C2 C7 S1 -97.4(4) . . . . ? C13 C8 C9 C10 1.0(6) . . . . ? S1 C8 C9 C10 -178.9(3) . . . . ? C8 C9 C10 C11 -0.6(6) . . . . ? C9 C10 C11 C12 0.3(7) . . . . ? C10 C11 C12 C13 -0.4(7) . . . . ? C9 C8 C13 C12 -1.2(5) . . . . ? S1 C8 C13 C12 178.8(3) . . . . ? C9 C8 C13 N1 177.7(3) . . . . ? S1 C8 C13 N1 -2.4(4) . . . . ? C11 C12 C13 C8 0.9(6) . . . . ? C11 C12 C13 N1 -177.9(4) . . . . ? N1 C14 C15 C16 2.0(6) . . . . ? N1 C14 C15 C20 -179.2(4) . . . . ? C20 C15 C16 O1 -178.7(4) . . . . ? C14 C15 C16 O1 0.2(7) . . . . ? C20 C15 C16 C17 0.3(7) . . . . ? C14 C15 C16 C17 179.2(5) . . . . ? O1 C16 C17 C18 179.5(5) . . . . ? C15 C16 C17 C18 0.5(8) . . . . ? C16 C17 C18 C19 -1.6(10) . . . . ? C17 C18 C19 C20 1.9(12) . . . . ? C18 C19 C20 C15 -1.0(10) . . . . ? C16 C15 C20 C19 -0.1(8) . . . . ? C14 C15 C20 C19 -179.0(5) . . . . ? C5 C6 C21 S2 97.0(4) . . . . ? C1 C6 C21 S2 -83.9(4) . . . . ? C27 C22 C23 C24 -2.0(10) . . . . ? S2 C22 C23 C24 -178.9(6) . . . . ? C22 C23 C24 C25 -3.6(12) . . . . ? C23 C24 C25 C26 5.6(13) . . . . ? C24 C25 C26 C27 -2.2(11) . . . . ? C23 C22 C27 C26 5.2(8) . . . . ? S2 C22 C27 C26 -177.8(4) . . . . ? C23 C22 C27 N2 -177.2(5) . . . . ? S2 C22 C27 N2 -0.3(6) . . . . ? C25 C26 C27 C22 -3.3(9) . . . . ? C25 C26 C27 N2 179.4(6) . . . . ? N2 C28 C29 C30 3.0(8) . . . . ? N2 C28 C29 C34 -177.3(5) . . . . ? C34 C29 C30 O2 179.7(5) . . . . ? C28 C29 C30 O2 -0.6(8) . . . . ? C34 C29 C30 C31 -1.5(8) . . . . ? C28 C29 C30 C31 178.2(5) . . . . ? O2 C30 C31 C32 179.4(6) . . . . ? C29 C30 C31 C32 0.6(10) . . . . ? C30 C31 C32 C33 2.5(12) . . . . ? C31 C32 C33 C34 -4.6(12) . . . . ? C32 C33 C34 C29 3.6(10) . . . . ? C30 C29 C34 C33 -0.6(9) . . . . ? C28 C29 C34 C33 179.7(6) . . . . ? C15 C14 N1 C13 178.6(3) . . . . ? C8 C13 N1 C14 179.6(3) . . . . ? C12 C13 N1 C14 -1.5(6) . . . . ? C29 C28 N2 C27 -179.3(4) . . . . ? C22 C27 N2 C28 157.0(5) . . . . ? C26 C27 N2 C28 -25.6(7) . . . . ? C9 C8 S1 C7 -7.7(4) . . . . ? C13 C8 S1 C7 172.4(3) . . . . ? C2 C7 S1 C8 -176.4(3) . . . . ? C27 C22 S2 C21 144.2(4) . . . . ? C23 C22 S2 C21 -38.9(6) . . . . ? C6 C21 S2 C22 159.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.265 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.054