Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _audit_creation_method 'RAELSPUB and manual entry' _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Marcia Scudder' 'Solhe Alshahateet' 'Roger Bishop' 'Donald C. Craig' 'Fethi Kooli' _publ_contact_author_name 'Marcia Scudder' _publ_contact_author_address ; School of Chemistry University of New South Wales Sydney NSW 2052 AUSTRALIA ; _publ_contact_author_email M.SCUDDER@UNSW.EDU.AU _publ_requested_journal CrystEngComm _publ_section_title ; The Janus-like behaviour of sulphur in substituted diquinoline inclusion crystal structures ; _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; data_DRB327 _database_code_depnum_ccdc_archive 'CCDC 659336' _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C34 H22 Br2 N2 S,C2 H2 Cl4' _chemical_formula_sum 'C36 H24 Br2 Cl4 N2 S' _chemical_formula_iupac ? _chemical_formula_weight 818.3 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 10.067(5) _cell_length_b 10.289(5) _cell_length_c 17.046(7) _cell_angle_alpha 76.54(3) _cell_angle_beta 88.64(3) _cell_angle_gamma 85.93(3) _cell_volume 1713(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.59 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816.0 _exptl_absorpt_coefficient_mu 2.750 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_T_max 0.75 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 6229 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 6007 _reflns_number_gt 4087 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.053 _refine_ls_wR_factor_ref 0.064 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 4087 _refine_ls_number_parameters 225 _refine_ls_goodness_of_fit_ref 1.83 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.006 _refine_diff_density_max 0.68 _refine_diff_density_min -0.81 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.53425(7) 0.47114(7) 0.88688(4) 0.0542(2) Uani Br 1.0 Br2 0.96084(6) 0.57987(8) 0.57719(4) 0.0591(3) Uani Br 1.0 S1 0.78095(15) 0.45544(15) 0.74713(9) 0.0401(5) Uani S 1.0 N1 0.8171(4) 0.8197(5) 0.7701(3) 0.0345(8) Uani N 1.0 N2 0.4741(4) 0.5756(5) 0.6050(3) 0.038(1) Uani N 1.0 C1 0.8294(5) 0.6258(6) 0.7187(3) 0.0338(6) Uani C 1.0 C2 0.7492(5) 0.7207(5) 0.7597(3) 0.0299(6) Uani C 1.0 C3 0.6131(5) 0.7072(5) 0.7820(3) 0.0289(7) Uani C 1.0 C4 0.5439(5) 0.5853(6) 0.7764(3) 0.0319(8) Uani C 1.0 C5 0.6090(5) 0.5054(6) 0.7196(3) 0.0351(6) Uani C 1.0 C6 0.5909(5) 0.5862(6) 0.6339(3) 0.0333(7) Uani C 1.0 C7 0.6880(5) 0.6704(6) 0.5912(3) 0.0329(9) Uani C 1.0 C8 0.8206(5) 0.6798(6) 0.6272(3) 0.034(1) Uani C 1.0 C9 0.7544(5) 0.9147(6) 0.8038(3) 0.0329(8) Uani C 1.0 C10 0.8312(6) 1.0162(6) 0.8192(4) 0.045(1) Uani C 1.0 C11 0.7730(7) 1.1135(7) 0.8539(4) 0.056(1) Uani C 1.0 C12 0.6371(7) 1.1169(7) 0.8727(5) 0.063(1) Uani C 1.0 C13 0.5592(6) 1.0197(7) 0.8592(4) 0.0529(9) Uani C 1.0 C14 0.6177(5) 0.9144(6) 0.8247(3) 0.0342(9) Uani C 1.0 C15 0.5456(5) 0.8065(5) 0.8124(3) 0.0309(9) Uani C 1.0 C16 0.4416(6) 0.6494(6) 0.5297(4) 0.0404(9) Uani C 1.0 C17 0.3151(6) 0.6368(7) 0.4989(4) 0.050(1) Uani C 1.0 C18 0.2785(7) 0.7073(8) 0.4243(4) 0.059(2) Uani C 1.0 C19 0.3650(7) 0.7934(8) 0.3770(4) 0.061(2) Uani C 1.0 C20 0.4881(6) 0.8088(7) 0.4047(4) 0.052(1) Uani C 1.0 C21 0.5298(6) 0.7350(6) 0.4823(3) 0.0405(9) Uani C 1.0 C22 0.6561(5) 0.7474(6) 0.5150(3) 0.036(1) Uani C 1.0 C23 0.4035(4) 0.7981(4) 0.8388(2) 0.037(2) Uani C 1.0 C24 0.3027(4) 0.8140(5) 0.7831(3) 0.049(2) Uani C 1.0 C25 0.1709(4) 0.7995(5) 0.8098(4) 0.061(2) Uani C 1.0 C26 0.1419(5) 0.7698(5) 0.8903(3) 0.064(2) Uani C 1.0 C27 0.2410(5) 0.7540(5) 0.9456(3) 0.065(2) Uani C 1.0 C28 0.3735(4) 0.7680(5) 0.9202(3) 0.051(2) Uani C 1.0 C29 0.7518(5) 0.8381(5) 0.4664(3) 0.044(2) Uani C 1.0 C30 0.7679(5) 0.9624(5) 0.4811(3) 0.059(2) Uani C 1.0 C31 0.8618(6) 1.0440(5) 0.4365(3) 0.078(2) Uani C 1.0 C32 0.9371(5) 1.0010(6) 0.3787(3) 0.082(2) Uani C 1.0 C33 0.9218(5) 0.8783(7) 0.3638(3) 0.079(2) Uani C 1.0 C34 0.8284(5) 0.7952(5) 0.4078(3) 0.059(2) Uani C 1.0 Cl1T 0.2314(3) 0.2990(4) 1.0090(2) 0.170(2) Uani Cl 1.0 Cl2T 0.0115(2) 0.4201(3) 0.9010(2) 0.1014(8) Uani Cl 1.0 Cl3T 0.1667(3) 0.1503(3) 0.8659(3) 0.191(2) Uani Cl 1.0 Cl4T 0.2141(4) 0.4145(5) 0.7555(2) 0.182(2) Uani Cl 1.0 C1T 0.1853(6) 0.3819(9) 0.9086(4) 0.096(3) Uani C 1.0 C2T 0.2378(10) 0.3069(7) 0.8547(6) 0.126(4) Uani C 1.0 HC1 0.9247 0.6252 0.7343 0.037 Uani H 1.0 HC4 0.4509 0.6147 0.7575 0.031 Uani H 1.0 HC5 0.5605 0.4221 0.7255 0.039 Uani H 1.0 HC8 0.8411 0.7762 0.6145 0.033 Uani H 1.0 HC10 0.9280 1.0167 0.8047 0.054 Uani H 1.0 HC11 0.8285 1.1832 0.8660 0.069 Uani H 1.0 HC12 0.5959 1.1909 0.8961 0.083 Uani H 1.0 HC13 0.4622 1.0225 0.8735 0.068 Uani H 1.0 HC17 0.2522 0.5755 0.5326 0.056 Uani H 1.0 HC18 0.1889 0.6973 0.4030 0.069 Uani H 1.0 HC19 0.3368 0.8448 0.3220 0.073 Uani H 1.0 HC20 0.5487 0.8720 0.3704 0.060 Uani H 1.0 HC24 0.3239 0.8358 0.7241 0.062 Uani H 1.0 HC25 0.0976 0.8110 0.7696 0.082 Uani H 1.0 HC26 0.0475 0.7596 0.9089 0.079 Uani H 1.0 HC27 0.2188 0.7322 1.0045 0.091 Uani H 1.0 HC28 0.4460 0.7564 0.9608 0.065 Uani H 1.0 HC30 0.7128 0.9940 0.5235 0.073 Uani H 1.0 HC31 0.8738 1.1341 0.4469 0.104 Uani H 1.0 HC32 1.0040 1.0598 0.3470 0.104 Uani H 1.0 HC33 0.9774 0.8476 0.3213 0.106 Uani H 1.0 HC34 0.8172 0.7053 0.3969 0.073 Uani H 1.0 HC1T 0.2285 0.4690 0.8956 0.096 Uani H 1.0 HC2T 0.3357 0.2893 0.8644 0.126 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0697(5) 0.0451(4) 0.0448(4) -0.0140(3) 0.0116(3) -0.0024(3) Br Br2 0.0387(4) 0.0866(6) 0.0558(5) 0.0024(4) 0.0115(3) -0.0275(4) Br S1 0.0381(8) 0.0351(7) 0.0463(9) 0.0004(6) -0.0015(6) -0.0087(6) S N1 0.032(2) 0.040(2) 0.031(2) -0.007(1) 0.002(1) -0.005(1) N N2 0.031(2) 0.046(2) 0.042(2) -0.007(1) 0.005(1) -0.019(1) N C1 0.029(1) 0.0375(8) 0.035(1) -0.0015(6) -0.0003(8) -0.0094(8) C C2 0.027(1) 0.0349(8) 0.027(1) -0.0039(7) 0.000(1) -0.0061(8) C C3 0.029(1) 0.0330(8) 0.025(2) -0.0055(7) 0.000(1) -0.0045(8) C C4 0.033(1) 0.0323(8) 0.030(1) -0.0068(9) 0.001(1) -0.0043(8) C C5 0.0354(8) 0.0324(8) 0.038(2) -0.0053(8) 0.0012(9) -0.0087(7) C C6 0.032(1) 0.0366(9) 0.034(1) -0.0065(8) 0.002(1) -0.013(1) C C7 0.031(2) 0.041(1) 0.031(1) -0.0061(9) 0.003(1) -0.0136(8) C C8 0.029(1) 0.041(1) 0.034(1) -0.0042(9) 0.003(1) -0.0133(7) C C9 0.038(1) 0.031(1) 0.027(2) -0.006(1) -0.003(1) 0.000(1) C C10 0.052(2) 0.040(2) 0.041(2) -0.016(2) -0.002(2) -0.006(2) C C11 0.070(3) 0.041(2) 0.060(3) -0.014(2) -0.006(2) -0.016(2) C C12 0.070(3) 0.045(2) 0.080(3) -0.001(2) -0.004(3) -0.031(2) C C13 0.051(2) 0.044(2) 0.069(3) 0.004(2) -0.002(2) -0.026(2) C C14 0.037(1) 0.030(1) 0.034(2) 0.001(1) -0.004(1) -0.005(1) C C15 0.029(2) 0.032(1) 0.029(2) 0.001(1) -0.002(1) -0.004(1) C C16 0.032(1) 0.050(2) 0.044(1) -0.003(1) 0.001(1) -0.020(1) C C17 0.036(1) 0.067(3) 0.055(2) -0.005(1) -0.004(1) -0.025(2) C C18 0.044(2) 0.078(3) 0.059(2) -0.001(2) -0.013(2) -0.025(2) C C19 0.055(2) 0.075(3) 0.052(2) -0.001(2) -0.016(2) -0.016(2) C C20 0.052(2) 0.062(3) 0.043(2) -0.004(2) -0.008(1) -0.011(1) C C21 0.038(1) 0.047(2) 0.039(1) -0.002(1) 0.000(1) -0.015(1) C C22 0.035(1) 0.041(2) 0.034(2) -0.004(1) 0.004(1) -0.013(2) C C23 0.032(2) 0.033(3) 0.045(2) 0.000(1) 0.002(1) -0.008(2) C C24 0.032(2) 0.054(3) 0.056(2) -0.002(2) -0.004(1) -0.006(2) C C25 0.032(2) 0.067(4) 0.079(3) -0.004(2) -0.002(1) -0.006(3) C C26 0.036(1) 0.065(4) 0.086(3) -0.004(2) 0.014(2) -0.011(3) C C27 0.045(2) 0.083(4) 0.066(2) -0.009(2) 0.019(2) -0.014(3) C C28 0.041(2) 0.064(3) 0.048(2) -0.006(2) 0.009(1) -0.011(2) C C29 0.045(2) 0.052(2) 0.033(2) -0.009(2) -0.003(2) -0.004(2) C C30 0.069(3) 0.053(3) 0.054(3) -0.021(2) -0.005(2) -0.006(2) C C31 0.083(4) 0.073(3) 0.070(4) -0.039(3) -0.013(2) 0.008(2) C C32 0.065(3) 0.108(4) 0.057(3) -0.040(3) -0.008(2) 0.020(3) C C33 0.061(3) 0.117(5) 0.050(3) -0.024(3) 0.013(2) 0.000(3) C C34 0.055(3) 0.080(3) 0.041(2) -0.012(2) 0.010(2) -0.011(2) C Cl1T 0.110(2) 0.281(5) 0.078(2) -0.061(3) -0.036(2) 0.060(2) Cl Cl2T 0.059(1) 0.125(2) 0.111(2) -0.012(1) -0.012(1) -0.006(2) Cl Cl3T 0.118(3) 0.101(2) 0.372(6) -0.030(2) -0.038(3) -0.083(3) Cl Cl4T 0.221(4) 0.259(5) 0.075(2) -0.078(4) 0.001(2) -0.038(3) Cl C1T 0.056(6) 0.124(9) 0.116(8) -0.032(5) 0.004(5) -0.036(7) C C2T 0.079(7) 0.121(9) 0.197(9) -0.041(7) 0.004(8) -0.066(9) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.978(5) 1_555 1_555 no Br2 C8 1.980(5) 1_555 1_555 no S1 C1 1.806(6) 1_555 1_555 no S1 C5 1.811(6) 1_555 1_555 no N1 C2 1.313(6) 1_555 1_555 no N1 C9 1.357(7) 1_555 1_555 no N2 C6 1.307(7) 1_555 1_555 no N2 C16 1.364(7) 1_555 1_555 no C1 C2 1.508(7) 1_555 1_555 no C1 C8 1.531(7) 1_555 1_555 no C2 C3 1.421(7) 1_555 1_555 no C3 C4 1.501(7) 1_555 1_555 no C3 C15 1.380(7) 1_555 1_555 no C4 C5 1.519(7) 1_555 1_555 no C5 C6 1.513(7) 1_555 1_555 no C6 C7 1.424(7) 1_555 1_555 no C7 C8 1.501(7) 1_555 1_555 no C7 C22 1.387(7) 1_555 1_555 no C9 C10 1.418(8) 1_555 1_555 no C9 C14 1.413(8) 1_555 1_555 no C10 C11 1.368(9) 1_555 1_555 no C11 C12 1.398(9) 1_555 1_555 no C12 C13 1.376(9) 1_555 1_555 no C13 C14 1.434(8) 1_555 1_555 no C14 C15 1.426(7) 1_555 1_555 no C15 C23 1.491(7) 1_555 1_555 no C16 C17 1.414(8) 1_555 1_555 no C16 C21 1.400(8) 1_555 1_555 no C17 C18 1.355(9) 1_555 1_555 no C18 C19 1.392(10) 1_555 1_555 no C19 C20 1.370(9) 1_555 1_555 no C20 C21 1.419(8) 1_555 1_555 no C21 C22 1.426(8) 1_555 1_555 no C22 C29 1.488(7) 1_555 1_555 no C23 C24 1.381(4) 1_555 1_555 no C23 C28 1.381(4) 1_555 1_555 no C24 C25 1.400(4) 1_555 1_555 no C25 C26 1.364(4) 1_555 1_555 no C26 C27 1.364(4) 1_555 1_555 no C27 C28 1.400(4) 1_555 1_555 no C29 C30 1.381(4) 1_555 1_555 no C29 C34 1.381(4) 1_555 1_555 no C30 C31 1.400(4) 1_555 1_555 no C31 C32 1.364(4) 1_555 1_555 no C32 C33 1.364(4) 1_555 1_555 no C33 C34 1.400(4) 1_555 1_555 no Cl1T C1T 1.781(5) 1_555 1_555 no Cl2T C1T 1.767(6) 1_555 1_555 no Cl3T C2T 1.777(6) 1_555 1_555 no Cl4T C2T 1.803(8) 1_555 1_555 no C1T C2T 1.403(13) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C5 92.6(3) 1_555 1_555 1_555 no C2 N1 C9 118.5(5) 1_555 1_555 1_555 no C6 N2 C16 118.8(5) 1_555 1_555 1_555 no S1 C1 C2 113.9(4) 1_555 1_555 1_555 no S1 C1 C8 110.7(4) 1_555 1_555 1_555 no C2 C1 C8 108.9(4) 1_555 1_555 1_555 no N1 C2 C1 112.9(5) 1_555 1_555 1_555 no N1 C2 C3 123.6(5) 1_555 1_555 1_555 no C1 C2 C3 123.5(5) 1_555 1_555 1_555 no C2 C3 C4 121.4(5) 1_555 1_555 1_555 no C2 C3 C15 118.8(5) 1_555 1_555 1_555 no C4 C3 C15 119.8(5) 1_555 1_555 1_555 no Br1 C4 C3 107.1(3) 1_555 1_555 1_555 no Br1 C4 C5 110.1(4) 1_555 1_555 1_555 no C3 C4 C5 115.1(4) 1_555 1_555 1_555 no S1 C5 C4 110.7(4) 1_555 1_555 1_555 no S1 C5 C6 114.1(4) 1_555 1_555 1_555 no C4 C5 C6 108.6(4) 1_555 1_555 1_555 no N2 C6 C5 112.6(5) 1_555 1_555 1_555 no N2 C6 C7 123.9(5) 1_555 1_555 1_555 no C5 C6 C7 123.4(5) 1_555 1_555 1_555 no C6 C7 C8 121.9(5) 1_555 1_555 1_555 no C6 C7 C22 118.2(5) 1_555 1_555 1_555 no C8 C7 C22 119.9(5) 1_555 1_555 1_555 no Br2 C8 C1 107.4(4) 1_555 1_555 1_555 no Br2 C8 C7 109.7(4) 1_555 1_555 1_555 no C1 C8 C7 115.1(4) 1_555 1_555 1_555 no N1 C9 C10 117.8(5) 1_555 1_555 1_555 no N1 C9 C14 122.6(5) 1_555 1_555 1_555 no C10 C9 C14 119.6(5) 1_555 1_555 1_555 no C9 C10 C11 120.1(6) 1_555 1_555 1_555 no C10 C11 C12 120.9(6) 1_555 1_555 1_555 no C11 C12 C13 120.8(6) 1_555 1_555 1_555 no C12 C13 C14 119.7(6) 1_555 1_555 1_555 no C9 C14 C13 118.8(5) 1_555 1_555 1_555 no C9 C14 C15 117.9(5) 1_555 1_555 1_555 no C13 C14 C15 123.2(5) 1_555 1_555 1_555 no C3 C15 C14 118.5(5) 1_555 1_555 1_555 no C3 C15 C23 122.0(5) 1_555 1_555 1_555 no C14 C15 C23 119.4(5) 1_555 1_555 1_555 no N2 C16 C17 118.3(6) 1_555 1_555 1_555 no N2 C16 C21 122.1(5) 1_555 1_555 1_555 no C17 C16 C21 119.6(6) 1_555 1_555 1_555 no C16 C17 C18 120.5(6) 1_555 1_555 1_555 no C17 C18 C19 120.3(6) 1_555 1_555 1_555 no C18 C19 C20 120.9(6) 1_555 1_555 1_555 no C19 C20 C21 120.0(6) 1_555 1_555 1_555 no C16 C21 C20 118.6(6) 1_555 1_555 1_555 no C16 C21 C22 118.6(5) 1_555 1_555 1_555 no C20 C21 C22 122.7(6) 1_555 1_555 1_555 no C7 C22 C21 118.4(5) 1_555 1_555 1_555 no C7 C22 C29 121.6(5) 1_555 1_555 1_555 no C21 C22 C29 120.0(5) 1_555 1_555 1_555 no C15 C23 C24 120.9(4) 1_555 1_555 1_555 no C15 C23 C28 119.3(4) 1_555 1_555 1_555 no C24 C23 C28 119.8(4) 1_555 1_555 1_555 no C23 C24 C25 119.7(3) 1_555 1_555 1_555 no C24 C25 C26 120.2(4) 1_555 1_555 1_555 no C25 C26 C27 120.5(5) 1_555 1_555 1_555 no C26 C27 C28 120.2(4) 1_555 1_555 1_555 no C23 C28 C27 119.7(3) 1_555 1_555 1_555 no C22 C29 C30 120.8(4) 1_555 1_555 1_555 no C22 C29 C34 119.4(4) 1_555 1_555 1_555 no C30 C29 C34 119.8(4) 1_555 1_555 1_555 no C29 C30 C31 119.7(3) 1_555 1_555 1_555 no C30 C31 C32 120.2(4) 1_555 1_555 1_555 no C31 C32 C33 120.5(5) 1_555 1_555 1_555 no C32 C33 C34 120.2(4) 1_555 1_555 1_555 no C29 C34 C33 119.7(3) 1_555 1_555 1_555 no Cl1T C1T Cl2T 111.3(5) 1_555 1_555 1_555 no Cl1T C1T C2T 109.7(6) 1_555 1_555 1_555 no Cl2T C1T C2T 114.3(6) 1_555 1_555 1_555 no Cl3T C2T Cl4T 113.1(6) 1_555 1_555 1_555 no Cl3T C2T C1T 113.5(7) 1_555 1_555 1_555 no Cl4T C2T C1T 105.6(5) 1_555 1_555 1_555 no # Attachment '10_c4h8o_drb321.cif' data_DRB321 _database_code_depnum_ccdc_archive 'CCDC 659337' _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C34 H22 Br2 N2 S,C4 H8 O' _chemical_formula_sum 'C38 H30 Br2 N2 O S' _chemical_formula_iupac ? _chemical_formula_weight 722.5 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 10.204(5) _cell_length_b 10.564(5) _cell_length_c 15.804(7) _cell_angle_alpha 104.64(3) _cell_angle_beta 99.74(3) _cell_angle_gamma 93.26(3) _cell_volume 1616(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12 _cell_measurement_temperature 294 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.48 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732.0 _exptl_absorpt_coefficient_mu 2.584 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_T_max 0.75 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 5902 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 22 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 5676 _reflns_number_gt 2792 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.065 _refine_ls_wR_factor_ref 0.082 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2792 _refine_ls_number_parameters 198 _refine_ls_goodness_of_fit_ref 1.68 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.004 _refine_diff_density_max 1.02 _refine_diff_density_min -1.53 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.41996(12) 0.70091(11) 0.56678(7) 0.0721(5) Uani Br 1.0 Br2 0.93746(11) 0.85881(13) 0.90880(8) 0.0853(5) Uani Br 1.0 S1 0.7101(3) 0.8340(2) 0.7192(2) 0.0522(8) Uani S 1.0 N1 0.7459(7) 0.4621(7) 0.7007(5) 0.043(2) Uani N 1.0 N2 0.4519(7) 0.8379(7) 0.8773(5) 0.046(2) Uani N 1.0 C1 0.7710(8) 0.6929(9) 0.7529(6) 0.044(1) Uani C 1.0 C2 0.6805(8) 0.5691(8) 0.7103(5) 0.038(1) Uani C 1.0 C3 0.5387(8) 0.5600(8) 0.6862(5) 0.037(1) Uani C 1.0 C4 0.4696(8) 0.6838(8) 0.6905(5) 0.041(1) Uani C 1.0 C5 0.5507(9) 0.8096(8) 0.7510(6) 0.045(1) Uani C 1.0 C6 0.5581(9) 0.8030(8) 0.8452(6) 0.041(1) Uani C 1.0 C7 0.6671(8) 0.7547(8) 0.8925(6) 0.040(1) Uani C 1.0 C8 0.7901(8) 0.7199(8) 0.8533(6) 0.043(1) Uani C 1.0 C9 0.6746(9) 0.3415(9) 0.6692(6) 0.044(2) Uani C 1.0 C10 0.7471(10) 0.2295(10) 0.6562(6) 0.056(3) Uani C 1.0 C11 0.6806(12) 0.1076(10) 0.6258(7) 0.064(3) Uani C 1.0 C12 0.5404(12) 0.0873(10) 0.6082(7) 0.066(3) Uani C 1.0 C13 0.4698(10) 0.1933(10) 0.6199(6) 0.059(2) Uani C 1.0 C14 0.5336(9) 0.3233(9) 0.6488(6) 0.045(2) Uani C 1.0 C15 0.4674(9) 0.4391(9) 0.6580(6) 0.044(2) Uani C 1.0 C16 0.4432(9) 0.8311(9) 0.9597(6) 0.049(2) Uani C 1.0 C17 0.3286(10) 0.8715(11) 0.9957(7) 0.066(2) Uani C 1.0 C18 0.3140(11) 0.8613(12) 1.0772(8) 0.074(3) Uani C 1.0 C19 0.4117(11) 0.8096(11) 1.1291(7) 0.073(2) Uani C 1.0 C20 0.5215(11) 0.7680(10) 1.0977(7) 0.066(2) Uani C 1.0 C21 0.5418(9) 0.7782(9) 1.0127(6) 0.049(2) Uani C 1.0 C22 0.6567(9) 0.7384(9) 0.9753(6) 0.045(2) Uani C 1.0 C23 0.3155(7) 0.4229(7) 0.6314(4) 0.052(3) Uani C 1.0 C24 0.2368(8) 0.4560(7) 0.6949(5) 0.064(3) Uani C 1.0 C25 0.0978(8) 0.4444(8) 0.6683(7) 0.082(4) Uani C 1.0 C26 0.0418(9) 0.4007(8) 0.5801(6) 0.090(4) Uani C 1.0 C27 0.1187(9) 0.3677(8) 0.5168(6) 0.088(3) Uani C 1.0 C28 0.2578(8) 0.3787(7) 0.5423(5) 0.067(3) Uani C 1.0 C29 0.7624(7) 0.6806(7) 1.0268(5) 0.054(3) Uani C 1.0 C30 0.7532(8) 0.5461(8) 1.0143(5) 0.077(3) Uani C 1.0 C31 0.8532(11) 0.4909(9) 1.0609(6) 0.105(5) Uani C 1.0 C32 0.9584(9) 0.5703(10) 1.1180(6) 0.112(5) Uani C 1.0 C33 0.9684(8) 0.7033(12) 1.1308(5) 0.110(4) Uani C 1.0 C34 0.8692(9) 0.7601(8) 1.0847(5) 0.080(3) Uani C 1.0 O1Thf 0.0194(11) 0.8757(18) 0.6781(12) 0.239(7) Uani O 1.0 C1Thf 0.1577(13) 0.8792(21) 0.7126(15) 0.214(8) Uani C 1.0 C2Thf 0.2216(14) 0.9914(20) 0.6923(16) 0.221(9) Uani C 1.0 C3Thf 0.1312(21) 1.0153(27) 0.6221(18) 0.282(9) Uani C 1.0 C4Thf 0.0073(17) 0.9852(24) 0.6408(20) 0.266(9) Uani C 1.0 HC1 0.8600 0.6798 0.7354 0.050 Uani H 1.0 HC4 0.3851 0.6720 0.7131 0.040 Uani H 1.0 HC5 0.4996 0.8852 0.7431 0.051 Uani H 1.0 HC8 0.8177 0.6380 0.8690 0.042 Uani H 1.0 HC10 0.8471 0.2407 0.6696 0.066 Uani H 1.0 HC11 0.7328 0.0296 0.6155 0.077 Uani H 1.0 HC12 0.4933 -0.0039 0.5873 0.081 Uani H 1.0 HC13 0.3699 0.1792 0.6078 0.071 Uani H 1.0 HC17 0.2575 0.9082 0.9599 0.080 Uani H 1.0 HC18 0.2328 0.8908 1.1009 0.088 Uani H 1.0 HC19 0.3999 0.8035 1.1895 0.088 Uani H 1.0 HC20 0.5893 0.7296 1.1347 0.079 Uani H 1.0 HC24 0.2788 0.4881 0.7595 0.074 Uani H 1.0 HC25 0.0398 0.4682 0.7138 0.102 Uani H 1.0 HC26 -0.0576 0.3926 0.5615 0.113 Uani H 1.0 HC27 0.0758 0.3357 0.4524 0.115 Uani H 1.0 HC28 0.3150 0.3547 0.4963 0.078 Uani H 1.0 HC30 0.6756 0.4886 0.9723 0.099 Uani H 1.0 HC31 0.8476 0.3935 1.0523 0.147 Uani H 1.0 HC32 1.0296 0.5302 1.1511 0.146 Uani H 1.0 HC33 1.0463 0.7600 1.1730 0.155 Uani H 1.0 HC34 0.8757 0.8575 1.0937 0.103 Uani H 1.0 H1C1Thf 0.1931 0.7962 0.6832 0.313 Uani H 1.0 H2C1Thf 0.1733 0.8907 0.7784 0.331 Uani H 1.0 H1C2Thf 0.3085 0.9705 0.6736 0.288 Uani H 1.0 H2C2Thf 0.2378 1.0697 0.7453 0.353 Uani H 1.0 H1C3Thf 0.1421 0.9573 0.5635 0.353 Uani H 1.0 H2C3Thf 0.1437 1.1095 0.6212 0.494 Uani H 1.0 H1C4Thf -0.0622 0.9614 0.5850 0.324 Uani H 1.0 H2C4Thf -0.0178 1.0619 0.6845 0.456 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0907(9) 0.0734(9) 0.0554(7) 0.0215(7) 0.0078(6) 0.0243(6) Br Br2 0.0622(8) 0.095(1) 0.086(1) -0.0070(7) 0.0040(7) 0.0099(8) Br S1 0.061(2) 0.044(1) 0.059(2) 0.009(1) 0.020(1) 0.021(1) S N1 0.047(3) 0.052(2) 0.037(3) 0.018(2) 0.015(2) 0.016(2) N N2 0.043(3) 0.042(4) 0.051(3) 0.011(3) 0.011(2) 0.004(2) N C1 0.044(2) 0.043(2) 0.048(3) 0.009(1) 0.015(2) 0.013(2) C C2 0.041(2) 0.040(1) 0.037(2) 0.013(2) 0.013(2) 0.010(1) C C3 0.042(2) 0.038(2) 0.033(3) 0.014(1) 0.010(2) 0.010(2) C C4 0.048(2) 0.040(2) 0.039(2) 0.017(2) 0.010(2) 0.015(2) C C5 0.054(2) 0.036(2) 0.048(3) 0.015(2) 0.014(2) 0.016(2) C C6 0.048(3) 0.032(2) 0.043(2) 0.013(2) 0.011(2) 0.008(2) C C7 0.043(2) 0.034(2) 0.040(2) 0.009(2) 0.008(2) 0.005(2) C C8 0.041(2) 0.040(2) 0.046(3) 0.006(2) 0.009(2) 0.008(2) C C9 0.057(2) 0.048(2) 0.032(3) 0.019(2) 0.016(2) 0.015(2) C C10 0.076(3) 0.054(2) 0.046(4) 0.030(2) 0.021(3) 0.017(2) C C11 0.103(5) 0.050(2) 0.047(4) 0.029(2) 0.022(5) 0.015(2) C C12 0.104(5) 0.046(2) 0.050(4) 0.011(2) 0.015(4) 0.013(2) C C13 0.078(3) 0.048(2) 0.050(4) 0.003(2) 0.011(4) 0.014(2) C C14 0.058(2) 0.046(2) 0.034(3) 0.010(2) 0.013(2) 0.013(2) C C15 0.047(3) 0.050(2) 0.038(3) 0.009(2) 0.011(3) 0.014(2) C C16 0.047(3) 0.045(4) 0.051(2) 0.005(2) 0.014(2) 0.000(2) C C17 0.056(3) 0.077(5) 0.062(3) 0.014(3) 0.023(3) 0.002(3) C C18 0.065(4) 0.087(5) 0.064(3) 0.008(3) 0.030(3) 0.001(3) C C19 0.076(4) 0.086(5) 0.057(3) 0.005(4) 0.030(3) 0.007(3) C C20 0.072(4) 0.076(5) 0.050(3) 0.008(4) 0.022(3) 0.012(3) C C21 0.053(3) 0.046(4) 0.045(2) 0.001(2) 0.013(2) 0.004(2) C C22 0.049(3) 0.042(4) 0.040(3) 0.004(3) 0.007(3) 0.007(3) C C23 0.053(3) 0.055(6) 0.049(4) 0.003(3) 0.011(2) 0.015(4) C C24 0.059(3) 0.075(5) 0.067(3) 0.013(3) 0.023(3) 0.026(4) C C25 0.058(3) 0.101(7) 0.105(6) 0.017(4) 0.029(3) 0.050(6) C C26 0.054(3) 0.110(8) 0.116(7) 0.002(3) 0.006(3) 0.055(7) C C27 0.063(3) 0.110(7) 0.084(4) -0.006(4) -0.010(3) 0.032(5) C C28 0.061(3) 0.080(5) 0.054(4) -0.001(3) 0.000(3) 0.016(4) C C29 0.062(4) 0.061(4) 0.044(5) 0.018(4) 0.020(3) 0.013(4) C C30 0.112(5) 0.063(4) 0.065(5) 0.037(4) 0.026(3) 0.021(4) C C31 0.153(8) 0.111(5) 0.078(7) 0.083(6) 0.043(5) 0.044(6) C C32 0.115(6) 0.178(9) 0.071(7) 0.091(7) 0.038(4) 0.056(7) C C33 0.078(4) 0.174(9) 0.080(5) 0.037(5) 0.003(4) 0.042(6) C C34 0.066(5) 0.102(4) 0.067(5) 0.008(4) 0.002(3) 0.021(4) C O1Thf 0.111(7) 0.346(9) 0.304(9) 0.032(9) 0.037(9) 0.164(9) O C1Thf 0.116(7) 0.265(9) 0.294(9) 0.037(9) 0.029(9) 0.137(9) C C2Thf 0.134(8) 0.237(9) 0.304(9) 0.020(9) 0.014(9) 0.114(9) C C3Thf 0.148(9) 0.322(9) 0.422(9) 0.007(9) -0.009(9) 0.228(9) C C4Thf 0.138(8) 0.289(9) 0.408(9) 0.099(9) 0.043(9) 0.150(9) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.991(8) 1_555 1_555 no Br2 C8 1.959(8) 1_555 1_555 no S1 C1 1.813(9) 1_555 1_555 no S1 C5 1.806(9) 1_555 1_555 no N1 C2 1.334(10) 1_555 1_555 no N1 C9 1.361(11) 1_555 1_555 no N2 C6 1.305(10) 1_555 1_555 no N2 C16 1.339(11) 1_555 1_555 no C1 C2 1.491(12) 1_555 1_555 no C1 C8 1.516(11) 1_555 1_555 no C2 C3 1.425(11) 1_555 1_555 no C3 C4 1.513(11) 1_555 1_555 no C3 C15 1.362(11) 1_555 1_555 no C4 C5 1.526(12) 1_555 1_555 no C5 C6 1.498(12) 1_555 1_555 no C6 C7 1.426(11) 1_555 1_555 no C7 C8 1.515(11) 1_555 1_555 no C7 C22 1.383(11) 1_555 1_555 no C9 C10 1.421(12) 1_555 1_555 no C9 C14 1.411(12) 1_555 1_555 no C10 C11 1.352(13) 1_555 1_555 no C11 C12 1.404(15) 1_555 1_555 no C12 C13 1.356(13) 1_555 1_555 no C13 C14 1.414(12) 1_555 1_555 no C14 C15 1.419(12) 1_555 1_555 no C15 C23 1.524(11) 1_555 1_555 no C16 C17 1.427(12) 1_555 1_555 no C16 C21 1.428(12) 1_555 1_555 no C17 C18 1.351(14) 1_555 1_555 no C18 C19 1.406(15) 1_555 1_555 no C19 C20 1.352(13) 1_555 1_555 no C20 C21 1.423(13) 1_555 1_555 no C21 C22 1.438(12) 1_555 1_555 no C22 C29 1.493(11) 1_555 1_555 no C23 C24 1.379(6) 1_555 1_555 no C23 C28 1.379(6) 1_555 1_555 no C24 C25 1.398(7) 1_555 1_555 no C25 C26 1.363(7) 1_555 1_555 no C26 C27 1.363(7) 1_555 1_555 no C27 C28 1.398(7) 1_555 1_555 no C29 C30 1.379(6) 1_555 1_555 no C29 C34 1.379(6) 1_555 1_555 no C30 C31 1.398(7) 1_555 1_555 no C31 C32 1.363(7) 1_555 1_555 no C32 C33 1.363(7) 1_555 1_555 no C33 C34 1.398(7) 1_555 1_555 no O1Thf C1Thf 1.419(7) 1_555 1_555 no O1Thf C4Thf 1.427(12) 1_555 1_555 no C1Thf C2Thf 1.453(8) 1_555 1_555 no C2Thf C3Thf 1.402(12) 1_555 1_555 no C3Thf C4Thf 1.384(16) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C5 93.0(4) 1_555 1_555 1_555 no C2 N1 C9 119.0(7) 1_555 1_555 1_555 no C6 N2 C16 119.6(8) 1_555 1_555 1_555 no S1 C1 C2 113.1(6) 1_555 1_555 1_555 no S1 C1 C8 109.6(6) 1_555 1_555 1_555 no C2 C1 C8 109.3(7) 1_555 1_555 1_555 no N1 C2 C1 112.6(7) 1_555 1_555 1_555 no N1 C2 C3 121.6(8) 1_555 1_555 1_555 no C1 C2 C3 125.7(7) 1_555 1_555 1_555 no C2 C3 C4 119.8(8) 1_555 1_555 1_555 no C2 C3 C15 119.2(8) 1_555 1_555 1_555 no C4 C3 C15 120.9(8) 1_555 1_555 1_555 no Br1 C4 C3 107.8(5) 1_555 1_555 1_555 no Br1 C4 C5 110.2(6) 1_555 1_555 1_555 no C3 C4 C5 115.1(7) 1_555 1_555 1_555 no S1 C5 C4 111.0(6) 1_555 1_555 1_555 no S1 C5 C6 115.1(6) 1_555 1_555 1_555 no C4 C5 C6 107.5(7) 1_555 1_555 1_555 no N2 C6 C5 113.5(8) 1_555 1_555 1_555 no N2 C6 C7 123.7(8) 1_555 1_555 1_555 no C5 C6 C7 122.7(8) 1_555 1_555 1_555 no C6 C7 C8 121.5(8) 1_555 1_555 1_555 no C6 C7 C22 118.0(8) 1_555 1_555 1_555 no C8 C7 C22 120.5(8) 1_555 1_555 1_555 no Br2 C8 C1 109.2(6) 1_555 1_555 1_555 no Br2 C8 C7 110.0(6) 1_555 1_555 1_555 no C1 C8 C7 115.3(7) 1_555 1_555 1_555 no N1 C9 C10 117.7(9) 1_555 1_555 1_555 no N1 C9 C14 123.2(8) 1_555 1_555 1_555 no C10 C9 C14 119.1(9) 1_555 1_555 1_555 no C9 C10 C11 119.8(10) 1_555 1_555 1_555 no C10 C11 C12 121.9(9) 1_555 1_555 1_555 no C11 C12 C13 118.9(10) 1_555 1_555 1_555 no C12 C13 C14 121.8(10) 1_555 1_555 1_555 no C9 C14 C13 118.4(9) 1_555 1_555 1_555 no C9 C14 C15 116.3(8) 1_555 1_555 1_555 no C13 C14 C15 125.3(9) 1_555 1_555 1_555 no C3 C15 C14 120.5(8) 1_555 1_555 1_555 no C3 C15 C23 121.7(8) 1_555 1_555 1_555 no C14 C15 C23 117.7(8) 1_555 1_555 1_555 no N2 C16 C17 119.8(9) 1_555 1_555 1_555 no N2 C16 C21 122.7(8) 1_555 1_555 1_555 no C17 C16 C21 117.5(9) 1_555 1_555 1_555 no C16 C17 C18 121.4(10) 1_555 1_555 1_555 no C17 C18 C19 120.8(10) 1_555 1_555 1_555 no C18 C19 C20 120.3(10) 1_555 1_555 1_555 no C19 C20 C21 120.8(10) 1_555 1_555 1_555 no C16 C21 C20 119.2(9) 1_555 1_555 1_555 no C16 C21 C22 116.6(8) 1_555 1_555 1_555 no C20 C21 C22 124.2(9) 1_555 1_555 1_555 no C7 C22 C21 119.3(8) 1_555 1_555 1_555 no C7 C22 C29 121.4(8) 1_555 1_555 1_555 no C21 C22 C29 119.2(8) 1_555 1_555 1_555 no C15 C23 C24 120.7(6) 1_555 1_555 1_555 no C15 C23 C28 118.9(6) 1_555 1_555 1_555 no C24 C23 C28 120.4(7) 1_555 1_555 1_555 no C23 C24 C25 119.4(6) 1_555 1_555 1_555 no C24 C25 C26 119.7(7) 1_555 1_555 1_555 no C25 C26 C27 121.3(8) 1_555 1_555 1_555 no C26 C27 C28 119.7(7) 1_555 1_555 1_555 no C23 C28 C27 119.4(6) 1_555 1_555 1_555 no C22 C29 C30 119.1(7) 1_555 1_555 1_555 no C22 C29 C34 120.5(7) 1_555 1_555 1_555 no C30 C29 C34 120.4(7) 1_555 1_555 1_555 no C29 C30 C31 119.4(6) 1_555 1_555 1_555 no C30 C31 C32 119.7(7) 1_555 1_555 1_555 no C31 C32 C33 121.3(8) 1_555 1_555 1_555 no C32 C33 C34 119.7(7) 1_555 1_555 1_555 no C29 C34 C33 119.4(6) 1_555 1_555 1_555 no C1Thf O1Thf C4Thf 105.7(10) 1_555 1_555 1_555 no O1Thf C1Thf C2Thf 105.4(9) 1_555 1_555 1_555 no C1Thf C2Thf C3Thf 105.1(9) 1_555 1_555 1_555 no C2Thf C3Thf C4Thf 103.7(12) 1_555 1_555 1_555 no O1Thf C4Thf C3Thf 106.4(9) 1_555 1_555 1_555 no # Attachment '10_c6h5cl_drb323.cif' data_DRB323 _database_code_depnum_ccdc_archive 'CCDC 659338' _audit_creation_method 'RAELSPUB and manual entry' _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C34 H22 Br2 N2 S,2(C6 H5 Cl)' _chemical_formula_sum 'C46 H32 Br2 Cl2 N2 S1' _chemical_formula_iupac ? _chemical_formula_weight 875.5 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 10.001(6) _cell_length_b 10.437(5) _cell_length_c 20.029(8) _cell_angle_alpha 78.18(3) _cell_angle_beta 77.99(3) _cell_angle_gamma 83.90(2) _cell_volume 1997(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.46 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884.0 _exptl_absorpt_coefficient_mu 2.234 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.56 _exptl_absorpt_correction_T_max 0.79 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 7238 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 39 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 7015 _reflns_number_gt 3804 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.059 _refine_ls_wR_factor_ref 0.075 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3804 _refine_ls_number_parameters 226 _refine_ls_goodness_of_fit_ref 1.63 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.006 _refine_diff_density_max 0.88 _refine_diff_density_min -1.05 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.94878(8) 0.08694(9) 0.57126(5) 0.0779(4) Uani Br 1.0 Br2 0.42137(10) 0.00406(8) 0.83708(4) 0.0781(4) Uani Br 1.0 S1 0.7197(2) -0.0192(2) 0.7184(1) 0.0548(8) Uani S 1.0 N1 0.4529(5) 0.0825(5) 0.5955(3) 0.050(2) Uani N 1.0 N2 0.7313(5) 0.3470(5) 0.7337(3) 0.044(1) Uani N 1.0 C1 0.5548(7) 0.0247(6) 0.6932(4) 0.049(1) Uani C 1.0 C2 0.5597(7) 0.0972(6) 0.6203(3) 0.045(1) Uani C 1.0 C3 0.6684(6) 0.1769(6) 0.5828(3) 0.0438(9) Uani C 1.0 C4 0.7869(6) 0.1900(6) 0.6141(3) 0.044(1) Uani C 1.0 C5 0.7706(6) 0.1474(6) 0.6920(3) 0.045(1) Uani C 1.0 C6 0.6703(6) 0.2454(6) 0.7271(3) 0.040(1) Uani C 1.0 C7 0.5268(6) 0.2316(6) 0.7467(3) 0.040(1) Uani C 1.0 C8 0.4652(6) 0.1087(6) 0.7423(3) 0.045(1) Uani C 1.0 C9 0.4422(7) 0.1471(7) 0.5304(4) 0.053(1) Uani C 1.0 C10 0.3259(7) 0.1272(8) 0.5030(4) 0.067(1) Uani C 1.0 C11 0.3122(8) 0.1902(9) 0.4381(5) 0.076(2) Uani C 1.0 C12 0.4083(8) 0.2746(9) 0.3968(4) 0.075(2) Uani C 1.0 C13 0.5210(8) 0.2959(8) 0.4220(4) 0.064(2) Uani C 1.0 C14 0.5420(7) 0.2312(7) 0.4887(4) 0.052(1) Uani C 1.0 C15 0.6557(6) 0.2465(6) 0.5176(3) 0.045(1) Uani C 1.0 C16 0.6505(7) 0.4447(6) 0.7615(3) 0.045(1) Uani C 1.0 C17 0.7175(7) 0.5519(7) 0.7708(4) 0.057(1) Uani C 1.0 C18 0.6394(9) 0.6507(7) 0.7992(4) 0.067(2) Uani C 1.0 C19 0.4995(9) 0.6517(7) 0.8166(4) 0.072(2) Uani C 1.0 C20 0.4318(8) 0.5508(7) 0.8071(4) 0.063(1) Uani C 1.0 C21 0.5073(7) 0.4443(6) 0.7800(3) 0.046(1) Uani C 1.0 C22 0.4456(6) 0.3319(6) 0.7719(3) 0.042(1) Uani C 1.0 C23 0.7625(5) 0.3354(5) 0.4754(3) 0.054(2) Uani C 1.0 C24 0.7632(6) 0.4614(6) 0.4870(3) 0.071(2) Uani C 1.0 C25 0.8676(7) 0.5417(5) 0.4492(3) 0.094(3) Uani C 1.0 C26 0.9687(6) 0.4958(7) 0.4009(3) 0.099(4) Uani C 1.0 C27 0.9689(5) 0.3715(7) 0.3891(3) 0.090(3) Uani C 1.0 C28 0.8653(6) 0.2900(5) 0.4264(3) 0.068(2) Uani C 1.0 C29 0.2932(5) 0.3261(5) 0.7945(2) 0.047(2) Uani C 1.0 C30 0.2085(6) 0.3426(5) 0.7465(3) 0.058(2) Uani C 1.0 C31 0.0669(5) 0.3355(5) 0.7691(3) 0.071(2) Uani C 1.0 C32 0.0120(6) 0.3123(6) 0.8385(3) 0.079(3) Uani C 1.0 C33 0.0946(6) 0.2958(6) 0.8864(3) 0.084(3) Uani C 1.0 C34 0.2365(5) 0.3026(5) 0.8647(3) 0.065(2) Uani C 1.0 ClCb1 0.7920(9) 0.4652(8) 1.0152(4) 0.294(8) Uani Cl 0.70 C1Cb1 0.7397(7) 0.3297(7) 0.9975(3) 0.123(4) Uani C 0.70 C2Cb1 0.7955(11) 0.2069(8) 1.0241(4) 0.144(4) Uani C 0.70 C3Cb1 0.7530(12) 0.0965(8) 1.0097(6) 0.178(4) Uani C 0.70 C4Cb1 0.6542(11) 0.1084(10) 0.9686(5) 0.207(6) Uani C 0.70 C5Cb1 0.5984(11) 0.2317(12) 0.9421(6) 0.212(6) Uani C 0.70 C6Cb1 0.6411(11) 0.3418(9) 0.9566(4) 0.162(4) Uani C 0.70 ClCb1' 0.5810(22) 0.1575(24) 0.9300(10) 0.303(9) Uani Cl 0.30 C1Cb1' 0.6567(15) 0.2522(18) 0.9681(7) 0.128(4) Uani C 0.30 C2Cb1' 0.6222(24) 0.3862(20) 0.9591(14) 0.201(6) Uani C 0.30 C3Cb1' 0.6837(31) 0.4634(21) 0.9901(16) 0.251(8) Uani C 0.30 C4Cb1' 0.7804(28) 0.4068(29) 1.0303(13) 0.248(6) Uani C 0.30 C5Cb1' 0.8148(25) 0.2723(30) 1.0392(11) 0.187(4) Uani C 0.30 C6Cb1' 0.7531(20) 0.1954(22) 1.0081(10) 0.117(4) Uani C 0.30 ClCb2 1.1692(9) 0.2017(9) 0.0862(4) 0.249(5) Uani Cl 0.67 C1Cb2 1.0441(8) 0.1749(7) 0.1573(4) 0.154(4) Uani C 0.67 C2Cb2 0.9818(11) 0.2796(9) 0.1879(5) 0.170(5) Uani C 0.67 C3Cb2 0.8799(12) 0.2581(13) 0.2458(6) 0.185(4) Uani C 0.67 C4Cb2 0.8397(10) 0.1312(14) 0.2734(5) 0.191(4) Uani C 0.67 C5Cb2 0.9024(11) 0.0264(11) 0.2426(6) 0.164(4) Uani C 0.67 C6Cb2 1.0042(10) 0.0484(9) 0.1848(5) 0.142(4) Uani C 0.67 ClCb2' 0.7841(15) 0.1128(17) 0.2906(9) 0.233(5) Uani Cl 0.33 C1Cb2' 0.9099(14) 0.1502(15) 0.2207(8) 0.150(4) Uani C 0.33 C2Cb2' 0.9779(20) 0.0516(19) 0.1868(10) 0.142(4) Uani C 0.33 C3Cb2' 1.0803(22) 0.0819(27) 0.1299(11) 0.169(4) Uani C 0.33 C4Cb2' 1.1153(21) 0.2113(30) 0.1067(10) 0.210(5) Uani C 0.33 C5Cb2' 1.0469(26) 0.3100(24) 0.1408(12) 0.205(6) Uani C 0.33 C6Cb2' 0.9446(22) 0.2794(17) 0.1976(11) 0.173(5) Uani C 0.33 HC1 0.5085 -0.0582 0.6986 0.056 Uani H 1.0 HC4 0.8081 0.2844 0.6021 0.043 Uani H 1.0 HC5 0.8616 0.1500 0.7048 0.049 Uani H 1.0 HC8 0.3772 0.1353 0.7254 0.045 Uani H 1.0 HC10 0.2552 0.0672 0.5316 0.074 Uani H 1.0 HC11 0.2309 0.1755 0.4195 0.088 Uani H 1.0 HC12 0.3960 0.3196 0.3491 0.087 Uani H 1.0 HC13 0.5889 0.3582 0.3926 0.070 Uani H 1.0 HC17 0.8192 0.5551 0.7567 0.065 Uani H 1.0 HC18 0.6863 0.7243 0.8076 0.079 Uani H 1.0 HC19 0.4461 0.7264 0.8364 0.089 Uani H 1.0 HC20 0.3296 0.5528 0.8193 0.076 Uani H 1.0 HC24 0.6893 0.4952 0.5223 0.083 Uani H 1.0 HC25 0.8681 0.6328 0.4576 0.123 Uani H 1.0 HC26 1.0429 0.5536 0.3741 0.125 Uani H 1.0 HC27 1.0432 0.3386 0.3536 0.116 Uani H 1.0 HC28 0.8657 0.1990 0.4176 0.079 Uani H 1.0 HC30 0.2485 0.3596 0.6956 0.073 Uani H 1.0 HC31 0.0057 0.3474 0.7343 0.091 Uani H 1.0 HC32 -0.0893 0.3073 0.8544 0.099 Uani H 1.0 HC33 0.0537 0.2788 0.9371 0.118 Uani H 1.0 HC34 0.2968 0.2905 0.8998 0.081 Uani H 1.0 HC2Cb1 0.8664 0.1990 1.0535 0.255 Uani H 0.70 HC3Cb1 0.7928 0.0078 1.0287 0.303 Uani H 0.70 HC4Cb1 0.6231 0.0279 0.9581 0.349 Uani H 0.70 HC5Cb1 0.5274 0.2398 0.9126 0.373 Uani H 0.70 HC6Cb1 0.6014 0.4306 0.9377 0.276 Uani H 0.70 HC2Cb1' 0.5527 0.4263 0.9302 0.341 Uani H 0.30 HC3Cb1' 0.6592 0.5599 0.9838 0.416 Uani H 0.30 HC4Cb1' 0.8253 0.4629 1.0529 0.417 Uani H 0.30 HC5Cb1' 0.8843 0.2320 1.0680 0.317 Uani H 0.30 HC6Cb1' 0.7774 0.0988 1.0143 0.184 Uani H 0.30 HC2Cb2 1.0111 0.3705 0.1678 0.221 Uani H 0.67 HC3Cb2 0.8347 0.3331 0.2680 0.242 Uani H 0.67 HC4Cb2 0.7655 0.1154 0.3156 0.264 Uani H 0.67 HC5Cb2 0.8733 -0.0645 0.2626 0.211 Uani H 0.67 HC6Cb2 1.0496 -0.0265 0.1624 0.167 Uani H 0.67 HC2Cb2' 0.9523 -0.0411 0.2038 0.167 Uani H 0.33 HC3Cb2' 1.1296 0.0113 0.1053 0.210 Uani H 0.33 HC4Cb2' 1.1900 0.2335 0.0652 0.292 Uani H 0.33 HC5Cb2' 1.0723 0.4028 0.1240 0.275 Uani H 0.33 HC6Cb2' 0.8951 0.3498 0.2224 0.215 Uani H 0.33 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0464(5) 0.1059(8) 0.0788(6) 0.0125(5) 0.0007(4) -0.0331(5) Br Br2 0.1031(7) 0.0558(5) 0.0664(6) -0.0220(5) 0.0131(5) -0.0122(4) Br S1 0.053(1) 0.0445(9) 0.067(1) 0.0016(8) -0.0106(9) -0.0140(8) S N1 0.035(2) 0.059(3) 0.059(2) -0.004(2) -0.003(2) -0.026(2) N N2 0.042(2) 0.045(2) 0.047(3) -0.011(1) -0.009(2) -0.006(2) N C1 0.047(1) 0.0426(9) 0.058(2) -0.007(1) -0.004(1) -0.0163(9) C C2 0.040(2) 0.048(1) 0.052(2) -0.007(1) -0.002(1) -0.023(1) C C3 0.037(2) 0.051(1) 0.047(1) -0.006(1) -0.002(1) -0.023(1) C C4 0.035(1) 0.050(1) 0.050(2) -0.003(1) -0.003(2) -0.0218(9) C C5 0.039(1) 0.047(1) 0.051(2) 0.0001(7) -0.008(1) -0.0165(9) C C6 0.036(2) 0.045(1) 0.041(2) -0.0035(8) -0.006(2) -0.0129(8) C C7 0.037(2) 0.044(1) 0.040(2) -0.0064(9) -0.003(1) -0.0116(9) C C8 0.044(1) 0.0440(9) 0.047(2) -0.009(1) -0.002(2) -0.012(1) C C9 0.041(2) 0.064(2) 0.060(2) 0.001(2) -0.009(1) -0.029(2) C C10 0.049(2) 0.085(4) 0.077(3) 0.000(2) -0.020(2) -0.035(2) C C11 0.061(2) 0.099(4) 0.080(3) 0.008(2) -0.029(3) -0.037(3) C C12 0.070(3) 0.095(4) 0.068(2) 0.012(3) -0.027(2) -0.029(2) C C13 0.062(3) 0.077(4) 0.056(2) 0.007(2) -0.016(2) -0.021(2) C C14 0.047(2) 0.060(2) 0.052(2) 0.004(2) -0.008(1) -0.024(2) C C15 0.042(2) 0.049(3) 0.046(2) 0.001(2) -0.002(2) -0.020(2) C C16 0.051(2) 0.041(2) 0.045(2) -0.011(1) -0.011(1) -0.005(1) C C17 0.067(2) 0.048(2) 0.060(3) -0.020(2) -0.013(2) -0.011(2) C C18 0.086(3) 0.048(2) 0.072(4) -0.019(2) -0.013(3) -0.017(2) C C19 0.085(3) 0.048(2) 0.085(4) -0.007(2) -0.010(3) -0.026(2) C C20 0.065(2) 0.047(2) 0.079(4) -0.001(2) -0.008(3) -0.023(2) C C21 0.050(2) 0.039(2) 0.050(2) -0.004(1) -0.010(2) -0.008(2) C C22 0.040(2) 0.040(2) 0.046(2) -0.002(1) -0.009(2) -0.007(2) C C23 0.058(3) 0.057(3) 0.049(3) -0.007(2) -0.014(2) -0.008(2) C C24 0.092(3) 0.059(3) 0.066(3) -0.021(2) -0.019(2) -0.008(2) C C25 0.120(5) 0.084(3) 0.082(5) -0.050(4) -0.028(3) 0.003(3) C C26 0.095(4) 0.123(5) 0.077(5) -0.054(4) -0.021(3) 0.014(3) C C27 0.069(3) 0.124(5) 0.069(3) -0.026(3) -0.003(2) 0.001(3) C C28 0.060(3) 0.084(3) 0.056(3) -0.007(2) -0.004(2) -0.010(2) C C29 0.046(2) 0.041(4) 0.052(3) -0.001(2) -0.004(2) -0.011(3) C C30 0.050(2) 0.059(3) 0.066(2) -0.002(2) -0.014(2) -0.010(3) C C31 0.049(2) 0.069(4) 0.095(4) -0.003(2) -0.016(2) -0.014(4) C C32 0.047(2) 0.082(5) 0.103(4) -0.005(2) 0.001(2) -0.019(4) C C33 0.054(2) 0.112(5) 0.078(3) -0.011(3) 0.012(2) -0.018(4) C C34 0.053(2) 0.082(4) 0.055(3) -0.007(2) 0.004(2) -0.014(3) C ClCb1 0.332(9) 0.293(8) 0.256(8) -0.156(7) 0.117(7) -0.160(7) Cl C1Cb1 0.122(6) 0.170(7) 0.057(5) -0.036(5) 0.039(4) -0.016(4) C C2Cb1 0.123(7) 0.225(7) 0.052(5) -0.034(6) 0.000(4) 0.041(5) C C3Cb1 0.147(9) 0.158(7) 0.164(6) -0.020(5) 0.057(5) 0.034(5) C C4Cb1 0.201(7) 0.241(7) 0.176(7) -0.112(7) 0.047(5) -0.066(6) C C5Cb1 0.153(6) 0.351(9) 0.133(8) -0.100(6) -0.041(5) 0.010(8) C C6Cb1 0.099(6) 0.212(7) 0.126(7) -0.011(6) 0.008(4) 0.052(5) C ClCb1' 0.267(7) 0.481(9) 0.203(9) -0.205(9) -0.046(7) -0.072(9) Cl C1Cb1' 0.097(7) 0.199(7) 0.067(5) -0.038(5) 0.007(4) 0.013(4) C C2Cb1' 0.111(6) 0.212(8) 0.202(9) 0.009(7) 0.029(5) 0.069(6) C C3Cb1' 0.220(9) 0.167(7) 0.289(9) -0.026(6) 0.135(7) -0.045(6) C C4Cb1' 0.289(8) 0.311(8) 0.156(5) -0.141(7) 0.077(5) -0.126(6) C C5Cb1' 0.185(8) 0.323(8) 0.050(5) -0.090(7) -0.015(4) 0.001(5) C C6Cb1' 0.104(6) 0.167(7) 0.048(5) -0.023(5) 0.022(4) 0.024(5) C ClCb2 0.285(8) 0.299(8) 0.190(6) -0.089(6) -0.091(5) -0.028(5) Cl C1Cb2 0.195(7) 0.130(6) 0.180(6) -0.020(4) -0.130(5) -0.031(5) C C2Cb2 0.239(8) 0.111(6) 0.225(7) -0.001(5) -0.184(6) -0.041(5) C C3Cb2 0.196(7) 0.176(6) 0.255(8) 0.045(6) -0.172(6) -0.105(5) C C4Cb2 0.158(7) 0.234(7) 0.232(6) -0.011(4) -0.108(5) -0.085(5) C C5Cb2 0.176(7) 0.151(6) 0.213(6) -0.037(5) -0.127(5) -0.035(5) C C6Cb2 0.171(7) 0.114(6) 0.191(6) 0.000(4) -0.137(5) -0.044(5) C ClCb2' 0.164(7) 0.318(9) 0.263(7) -0.031(5) -0.092(5) -0.104(7) Cl C1Cb2' 0.158(7) 0.137(6) 0.206(6) 0.003(5) -0.133(5) -0.058(5) C C2Cb2' 0.171(7) 0.112(6) 0.194(6) -0.002(5) -0.139(5) -0.043(5) C C3Cb2' 0.199(8) 0.172(6) 0.184(6) 0.002(5) -0.124(5) -0.059(5) C C4Cb2' 0.266(8) 0.215(6) 0.184(6) -0.066(5) -0.117(5) -0.018(5) C C5Cb2' 0.312(9) 0.136(6) 0.224(7) -0.056(5) -0.188(6) -0.003(6) C C6Cb2' 0.232(8) 0.118(6) 0.237(7) 0.017(5) -0.190(6) -0.059(5) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.986(6) 1_555 1_555 no Br2 C8 1.974(6) 1_555 1_555 no S1 C1 1.810(7) 1_555 1_555 no S1 C5 1.806(7) 1_555 1_555 no N1 C2 1.303(7) 1_555 1_555 no N1 C9 1.359(8) 1_555 1_555 no N2 C6 1.321(7) 1_555 1_555 no N2 C16 1.369(8) 1_555 1_555 no C1 C2 1.495(9) 1_555 1_555 no C1 C8 1.535(9) 1_555 1_555 no C2 C3 1.426(8) 1_555 1_555 no C3 C4 1.480(8) 1_555 1_555 no C3 C15 1.382(9) 1_555 1_555 no C4 C5 1.512(9) 1_555 1_555 no C5 C6 1.527(8) 1_555 1_555 no C6 C7 1.421(8) 1_555 1_555 no C7 C8 1.507(8) 1_555 1_555 no C7 C22 1.369(8) 1_555 1_555 no C9 C10 1.435(9) 1_555 1_555 no C9 C14 1.416(10) 1_555 1_555 no C10 C11 1.359(11) 1_555 1_555 no C11 C12 1.391(11) 1_555 1_555 no C12 C13 1.383(10) 1_555 1_555 no C13 C14 1.414(10) 1_555 1_555 no C14 C15 1.416(9) 1_555 1_555 no C15 C23 1.493(8) 1_555 1_555 no C16 C17 1.424(9) 1_555 1_555 no C16 C21 1.404(9) 1_555 1_555 no C17 C18 1.371(10) 1_555 1_555 no C18 C19 1.370(11) 1_555 1_555 no C19 C20 1.375(10) 1_555 1_555 no C20 C21 1.414(9) 1_555 1_555 no C21 C22 1.434(8) 1_555 1_555 no C22 C29 1.501(8) 1_555 1_555 no C23 C24 1.383(4) 1_555 1_555 no C23 C28 1.383(4) 1_555 1_555 no C24 C25 1.400(5) 1_555 1_555 no C25 C26 1.366(5) 1_555 1_555 no C26 C27 1.366(5) 1_555 1_555 no C27 C28 1.400(5) 1_555 1_555 no C29 C30 1.383(4) 1_555 1_555 no C29 C34 1.383(4) 1_555 1_555 no C30 C31 1.400(5) 1_555 1_555 no C31 C32 1.366(5) 1_555 1_555 no C32 C33 1.366(5) 1_555 1_555 no C33 C34 1.400(5) 1_555 1_555 no ClCb1 C1Cb1 1.686(3) 1_555 1_555 no C1Cb1 C2Cb1 1.389(4) 1_555 1_555 no C1Cb1 C6Cb1 1.389(4) 1_555 1_555 no C2Cb1 C3Cb1 1.371(4) 1_555 1_555 no C3Cb1 C4Cb1 1.393(3) 1_555 1_555 no C4Cb1 C5Cb1 1.393(3) 1_555 1_555 no C5Cb1 C6Cb1 1.371(4) 1_555 1_555 no ClCb1' C1Cb1' 1.686(3) 1_555 1_555 no C1Cb1' C2Cb1' 1.389(4) 1_555 1_555 no C1Cb1' C6Cb1' 1.389(4) 1_555 1_555 no C2Cb1' C3Cb1' 1.371(4) 1_555 1_555 no C3Cb1' C4Cb1' 1.393(3) 1_555 1_555 no C4Cb1' C5Cb1' 1.393(3) 1_555 1_555 no C5Cb1' C6Cb1' 1.371(4) 1_555 1_555 no ClCb2 C1Cb2 1.686(3) 1_555 1_555 no C1Cb2 C2Cb2 1.389(4) 1_555 1_555 no C1Cb2 C6Cb2 1.389(4) 1_555 1_555 no C2Cb2 C3Cb2 1.371(4) 1_555 1_555 no C3Cb2 C4Cb2 1.393(3) 1_555 1_555 no C4Cb2 C5Cb2 1.393(3) 1_555 1_555 no C5Cb2 C6Cb2 1.371(4) 1_555 1_555 no ClCb2' C1Cb2' 1.686(3) 1_555 1_555 no C1Cb2' C2Cb2' 1.389(4) 1_555 1_555 no C1Cb2' C6Cb2' 1.389(4) 1_555 1_555 no C2Cb2' C3Cb2' 1.371(4) 1_555 1_555 no C3Cb2' C4Cb2' 1.393(3) 1_555 1_555 no C4Cb2' C5Cb2' 1.393(3) 1_555 1_555 no C5Cb2' C6Cb2' 1.371(4) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C5 92.8(3) 1_555 1_555 1_555 no C2 N1 C9 118.9(6) 1_555 1_555 1_555 no C6 N2 C16 117.5(5) 1_555 1_555 1_555 no S1 C1 C2 115.2(5) 1_555 1_555 1_555 no S1 C1 C8 109.9(5) 1_555 1_555 1_555 no C2 C1 C8 108.1(5) 1_555 1_555 1_555 no N1 C2 C1 112.9(6) 1_555 1_555 1_555 no N1 C2 C3 123.9(6) 1_555 1_555 1_555 no C1 C2 C3 123.2(6) 1_555 1_555 1_555 no C2 C3 C4 121.3(6) 1_555 1_555 1_555 no C2 C3 C15 117.4(6) 1_555 1_555 1_555 no C4 C3 C15 121.2(6) 1_555 1_555 1_555 no Br1 C4 C3 109.1(4) 1_555 1_555 1_555 no Br1 C4 C5 107.3(4) 1_555 1_555 1_555 no C3 C4 C5 117.0(5) 1_555 1_555 1_555 no S1 C5 C4 110.3(4) 1_555 1_555 1_555 no S1 C5 C6 113.3(4) 1_555 1_555 1_555 no C4 C5 C6 108.9(5) 1_555 1_555 1_555 no N2 C6 C5 112.2(5) 1_555 1_555 1_555 no N2 C6 C7 124.2(6) 1_555 1_555 1_555 no C5 C6 C7 123.5(6) 1_555 1_555 1_555 no C6 C7 C8 121.4(6) 1_555 1_555 1_555 no C6 C7 C22 118.1(6) 1_555 1_555 1_555 no C8 C7 C22 120.5(6) 1_555 1_555 1_555 no Br2 C8 C1 110.1(4) 1_555 1_555 1_555 no Br2 C8 C7 108.0(4) 1_555 1_555 1_555 no C1 C8 C7 115.0(5) 1_555 1_555 1_555 no N1 C9 C10 118.3(7) 1_555 1_555 1_555 no N1 C9 C14 122.5(6) 1_555 1_555 1_555 no C10 C9 C14 119.2(7) 1_555 1_555 1_555 no C9 C10 C11 119.8(8) 1_555 1_555 1_555 no C10 C11 C12 121.8(8) 1_555 1_555 1_555 no C11 C12 C13 119.6(8) 1_555 1_555 1_555 no C12 C13 C14 121.1(8) 1_555 1_555 1_555 no C9 C14 C13 118.5(7) 1_555 1_555 1_555 no C9 C14 C15 117.1(7) 1_555 1_555 1_555 no C13 C14 C15 124.4(7) 1_555 1_555 1_555 no C3 C15 C14 120.1(6) 1_555 1_555 1_555 no C3 C15 C23 121.3(6) 1_555 1_555 1_555 no C14 C15 C23 118.6(6) 1_555 1_555 1_555 no N2 C16 C17 117.3(6) 1_555 1_555 1_555 no N2 C16 C21 123.2(6) 1_555 1_555 1_555 no C17 C16 C21 119.6(6) 1_555 1_555 1_555 no C16 C17 C18 118.6(7) 1_555 1_555 1_555 no C17 C18 C19 122.2(7) 1_555 1_555 1_555 no C18 C19 C20 120.5(7) 1_555 1_555 1_555 no C19 C20 C21 119.8(7) 1_555 1_555 1_555 no C16 C21 C20 119.3(6) 1_555 1_555 1_555 no C16 C21 C22 117.2(6) 1_555 1_555 1_555 no C20 C21 C22 123.5(6) 1_555 1_555 1_555 no C7 C22 C21 119.6(6) 1_555 1_555 1_555 no C7 C22 C29 122.1(5) 1_555 1_555 1_555 no C21 C22 C29 118.2(5) 1_555 1_555 1_555 no C15 C23 C24 120.5(5) 1_555 1_555 1_555 no C15 C23 C28 120.0(5) 1_555 1_555 1_555 no C24 C23 C28 119.4(5) 1_555 1_555 1_555 no C23 C24 C25 119.9(4) 1_555 1_555 1_555 no C24 C25 C26 120.2(4) 1_555 1_555 1_555 no C25 C26 C27 120.4(6) 1_555 1_555 1_555 no C26 C27 C28 120.2(4) 1_555 1_555 1_555 no C23 C28 C27 119.9(4) 1_555 1_555 1_555 no C22 C29 C30 121.2(4) 1_555 1_555 1_555 no C22 C29 C34 119.4(4) 1_555 1_555 1_555 no C30 C29 C34 119.4(5) 1_555 1_555 1_555 no C29 C30 C31 119.9(4) 1_555 1_555 1_555 no C30 C31 C32 120.2(4) 1_555 1_555 1_555 no C31 C32 C33 120.4(6) 1_555 1_555 1_555 no C32 C33 C34 120.2(4) 1_555 1_555 1_555 no C29 C34 C33 119.9(4) 1_555 1_555 1_555 no ClCb1 C1Cb1 C2Cb1 119.7(1) 1_555 1_555 1_555 no ClCb1 C1Cb1 C6Cb1 119.7(1) 1_555 1_555 1_555 no C2Cb1 C1Cb1 C6Cb1 120.6(2) 1_555 1_555 1_555 no C1Cb1 C2Cb1 C3Cb1 119.8(3) 1_555 1_555 1_555 no C2Cb1 C3Cb1 C4Cb1 119.8(3) 1_555 1_555 1_555 no C3Cb1 C4Cb1 C5Cb1 120.3(3) 1_555 1_555 1_555 no C4Cb1 C5Cb1 C6Cb1 119.8(3) 1_555 1_555 1_555 no C1Cb1 C6Cb1 C5Cb1 119.8(3) 1_555 1_555 1_555 no ClCb1' C1Cb1' C2Cb1' 119.7(1) 1_555 1_555 1_555 no ClCb1' C1Cb1' C6Cb1' 119.7(1) 1_555 1_555 1_555 no C2Cb1' C1Cb1' C6Cb1' 120.6(3) 1_555 1_555 1_555 no C1Cb1' C2Cb1' C3Cb1' 119.8(3) 1_555 1_555 1_555 no C2Cb1' C3Cb1' C4Cb1' 119.8(3) 1_555 1_555 1_555 no C3Cb1' C4Cb1' C5Cb1' 120.3(3) 1_555 1_555 1_555 no C4Cb1' C5Cb1' C6Cb1' 119.8(3) 1_555 1_555 1_555 no C1Cb1' C6Cb1' C5Cb1' 119.8(3) 1_555 1_555 1_555 no ClCb2 C1Cb2 C2Cb2 119.7(1) 1_555 1_555 1_555 no ClCb2 C1Cb2 C6Cb2 119.7(1) 1_555 1_555 1_555 no C2Cb2 C1Cb2 C6Cb2 120.6(3) 1_555 1_555 1_555 no C1Cb2 C2Cb2 C3Cb2 119.8(3) 1_555 1_555 1_555 no C2Cb2 C3Cb2 C4Cb2 119.8(3) 1_555 1_555 1_555 no C3Cb2 C4Cb2 C5Cb2 120.3(3) 1_555 1_555 1_555 no C4Cb2 C5Cb2 C6Cb2 119.8(3) 1_555 1_555 1_555 no C1Cb2 C6Cb2 C5Cb2 119.8(3) 1_555 1_555 1_555 no ClCb2' C1Cb2' C2Cb2' 119.7(1) 1_555 1_555 1_555 no ClCb2' C1Cb2' C6Cb2' 119.7(1) 1_555 1_555 1_555 no C2Cb2' C1Cb2' C6Cb2' 120.6(3) 1_555 1_555 1_555 no C1Cb2' C2Cb2' C3Cb2' 119.8(3) 1_555 1_555 1_555 no C2Cb2' C3Cb2' C4Cb2' 119.8(3) 1_555 1_555 1_555 no C3Cb2' C4Cb2' C5Cb2' 120.3(3) 1_555 1_555 1_555 no C4Cb2' C5Cb2' C6Cb2' 119.8(3) 1_555 1_555 1_555 no C1Cb2' C6Cb2' C5Cb2' 119.8(3) 1_555 1_555 1_555 no # Attachment '10_ch2cl2_drb320.cif' data_DRB320 _database_code_depnum_ccdc_archive 'CCDC 659339' _audit_creation_method 'RAELSPUB and manual entry' _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C34 H22 Br2 N2 S,C H2 Cl2' _chemical_formula_sum 'C35 H24 Br2 Cl2 N2 S' _chemical_formula_iupac ? _chemical_formula_weight 735.4 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 10.085(4) _cell_length_b 10.509(4) _cell_length_c 15.811(6) _cell_angle_alpha 106.24(2) _cell_angle_beta 100.09(2) _cell_angle_gamma 92.01(2) _cell_volume 1578(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.55 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736.0 _exptl_absorpt_coefficient_mu 2.811 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.60 _exptl_absorpt_correction_T_max 0.69 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 5755 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 5536 _reflns_number_gt 3277 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.060 _refine_ls_wR_factor_ref 0.077 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3277 _refine_ls_number_parameters 196 _refine_ls_goodness_of_fit_ref 1.64 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.005 _refine_diff_density_max 1.17 _refine_diff_density_min -1.01 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.40709(9) 0.69170(9) 0.56528(5) 0.0611(3) Uani Br 1.0 Br2 0.93582(9) 0.85119(10) 0.91045(6) 0.0742(4) Uani Br 1.0 S1 0.7028(2) 0.8249(2) 0.7183(1) 0.0478(7) Uani S 1.0 N1 0.7450(6) 0.4499(6) 0.6984(4) 0.040(1) Uani N 1.0 N2 0.4431(6) 0.8382(6) 0.8781(4) 0.043(1) Uani N 1.0 C1 0.7660(7) 0.6840(7) 0.7528(5) 0.0408(8) Uani C 1.0 C2 0.6754(7) 0.5560(7) 0.7077(4) 0.0367(8) Uani C 1.0 C3 0.5313(7) 0.5505(7) 0.6837(4) 0.0363(8) Uani C 1.0 C4 0.4614(7) 0.6760(7) 0.6890(4) 0.0395(9) Uani C 1.0 C5 0.5423(7) 0.8030(7) 0.7489(5) 0.0430(8) Uani C 1.0 C6 0.5505(7) 0.8017(7) 0.8463(5) 0.0412(8) Uani C 1.0 C7 0.6618(7) 0.7521(7) 0.8935(5) 0.0404(7) Uani C 1.0 C8 0.7842(7) 0.7116(7) 0.8535(5) 0.0409(8) Uani C 1.0 C9 0.6763(8) 0.3285(7) 0.6663(4) 0.042(1) Uani C 1.0 C10 0.7501(9) 0.2156(8) 0.6525(5) 0.056(1) Uani C 1.0 C11 0.6853(11) 0.0904(8) 0.6226(6) 0.066(2) Uani C 1.0 C12 0.5457(11) 0.0732(8) 0.6082(5) 0.066(2) Uani C 1.0 C13 0.4674(9) 0.1790(8) 0.6178(5) 0.057(2) Uani C 1.0 C14 0.5321(8) 0.3115(7) 0.6465(5) 0.043(1) Uani C 1.0 C15 0.4601(7) 0.4285(7) 0.6546(4) 0.041(1) Uani C 1.0 C16 0.4341(7) 0.8318(7) 0.9619(5) 0.045(1) Uani C 1.0 C17 0.3188(8) 0.8731(8) 0.9963(6) 0.057(1) Uani C 1.0 C18 0.3060(9) 0.8670(9) 1.0798(6) 0.064(2) Uani C 1.0 C19 0.4044(10) 0.8170(9) 1.1302(6) 0.066(2) Uani C 1.0 C20 0.5176(9) 0.7743(9) 1.0999(5) 0.060(2) Uani C 1.0 C21 0.5376(8) 0.7820(7) 1.0132(5) 0.046(1) Uani C 1.0 C22 0.6530(7) 0.7395(7) 0.9773(5) 0.043(1) Uani C 1.0 C23 0.3093(6) 0.4116(6) 0.6261(4) 0.052(2) Uani C 1.0 C24 0.2264(7) 0.4477(6) 0.6880(4) 0.064(2) Uani C 1.0 C25 0.0864(6) 0.4339(7) 0.6591(6) 0.083(3) Uani C 1.0 C26 0.0308(8) 0.3848(7) 0.5697(5) 0.094(3) Uani C 1.0 C27 0.1125(7) 0.3488(7) 0.5081(5) 0.090(3) Uani C 1.0 C28 0.2527(6) 0.3620(6) 0.5359(4) 0.068(2) Uani C 1.0 C29 0.7609(6) 0.6831(6) 1.0294(4) 0.053(2) Uani C 1.0 C30 0.7606(7) 0.5474(7) 1.0156(4) 0.077(2) Uani C 1.0 C31 0.8635(9) 0.4966(8) 1.0646(5) 0.107(4) Uani C 1.0 C32 0.9646(8) 0.5807(9) 1.1261(5) 0.113(4) Uani C 1.0 C33 0.9652(7) 0.7152(10) 1.1400(4) 0.109(3) Uani C 1.0 C34 0.8631(7) 0.7676(7) 1.0916(4) 0.078(2) Uani C 1.0 C1Dcm 0.2033(13) 0.9824(11) 0.6895(8) 0.182(5) Uani C 0.74 Cl1Dcm 0.0953(8) 1.0584(9) 0.6277(8) 0.244(4) Uani Cl 0.74 Cl2Dcm 0.1237(9) 0.8597(11) 0.7179(5) 0.237(6) Uani Cl 0.74 C1Dcm' 0.1478(26) 0.8908(29) 0.6537(17) 0.144(5) Uani C 0.26 Cl1Dcm' 0.1325(22) 0.9799(27) 0.5783(14) 0.209(4) Uani Cl 0.26 Cl2Dcm' 0.0356(22) 0.9271(24) 0.7238(13) 0.220(6) Uani Cl 0.26 HC1 0.8566 0.6700 0.7361 0.043 Uani H 1.0 HC4 0.3770 0.6664 0.7124 0.039 Uani H 1.0 HC5 0.4897 0.8790 0.7405 0.047 Uani H 1.0 HC8 0.8116 0.6285 0.8682 0.040 Uani H 1.0 HC10 0.8512 0.2272 0.6647 0.065 Uani H 1.0 HC11 0.7389 0.0111 0.6111 0.080 Uani H 1.0 HC12 0.5003 -0.0191 0.5902 0.080 Uani H 1.0 HC13 0.3665 0.1637 0.6050 0.067 Uani H 1.0 HC17 0.2453 0.9073 0.9596 0.066 Uani H 1.0 HC18 0.2244 0.8991 1.1042 0.075 Uani H 1.0 HC19 0.3924 0.8120 1.1906 0.079 Uani H 1.0 HC20 0.5873 0.7374 1.1376 0.071 Uani H 1.0 HC24 0.2668 0.4837 0.7533 0.072 Uani H 1.0 HC25 0.0263 0.4600 0.7038 0.104 Uani H 1.0 HC26 -0.0697 0.3751 0.5494 0.119 Uani H 1.0 HC27 0.0714 0.3129 0.4429 0.117 Uani H 1.0 HC28 0.3121 0.3357 0.4908 0.077 Uani H 1.0 HC30 0.6869 0.4857 0.9707 0.101 Uani H 1.0 HC31 0.8635 0.3984 1.0546 0.150 Uani H 1.0 HC32 1.0381 0.5437 1.1610 0.149 Uani H 1.0 HC33 1.0393 0.7763 1.1850 0.156 Uani H 1.0 HC34 0.8638 0.8660 1.1019 0.102 Uani H 1.0 H1C1Dc' 0.2498 1.0509 0.7457 0.287 Uani H 0.74 H2C1Dc' 0.2719 0.9428 0.6537 0.201 Uani H 0.74 H1C1Dc 0.2415 0.9106 0.6905 0.217 Uani H 0.26 H2C1Dc 0.1324 0.7939 0.6201 0.175 Uani H 0.26 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0740(7) 0.0670(6) 0.0414(5) 0.0078(5) -0.0029(4) 0.0225(4) Br Br2 0.0522(6) 0.0835(7) 0.0702(7) -0.0072(5) -0.0051(5) 0.0079(5) Br S1 0.053(1) 0.044(1) 0.049(1) 0.0019(8) 0.0091(9) 0.0182(9) S N1 0.045(2) 0.048(2) 0.028(2) 0.007(2) 0.003(2) 0.014(1) N N2 0.038(2) 0.041(3) 0.042(2) 0.004(2) 0.000(2) 0.005(2) N C1 0.041(1) 0.043(1) 0.038(2) 0.0014(9) 0.006(1) 0.0122(9) C C2 0.038(2) 0.042(1) 0.030(2) 0.0036(8) 0.004(2) 0.0125(9) C C3 0.038(2) 0.042(1) 0.029(2) 0.0051(9) 0.003(1) 0.0126(9) C C4 0.043(1) 0.043(1) 0.032(2) 0.008(1) 0.003(2) 0.014(1) C C5 0.047(1) 0.041(1) 0.040(2) 0.006(1) 0.004(1) 0.014(1) C C6 0.041(2) 0.042(1) 0.036(2) 0.006(1) 0.001(1) 0.009(1) C C7 0.038(2) 0.044(1) 0.034(1) 0.005(1) 0.001(1) 0.007(1) C C8 0.038(2) 0.044(1) 0.036(2) 0.003(1) 0.003(1) 0.008(1) C C9 0.056(2) 0.045(2) 0.027(2) 0.008(1) 0.006(2) 0.013(1) C C10 0.076(2) 0.050(2) 0.044(3) 0.019(2) 0.011(3) 0.018(2) C C11 0.105(4) 0.046(2) 0.046(3) 0.017(2) 0.012(4) 0.016(2) C C12 0.107(4) 0.044(2) 0.043(3) -0.002(2) 0.004(3) 0.015(2) C C13 0.079(3) 0.048(2) 0.041(3) -0.010(2) 0.002(3) 0.017(2) C C14 0.056(2) 0.045(2) 0.028(2) -0.002(2) 0.006(2) 0.013(1) C C15 0.044(2) 0.050(2) 0.032(3) -0.002(2) 0.009(2) 0.016(2) C C16 0.045(2) 0.040(3) 0.043(2) 0.004(2) 0.006(2) 0.004(2) C C17 0.054(2) 0.056(3) 0.060(3) 0.011(2) 0.018(2) 0.012(2) C C18 0.068(3) 0.064(4) 0.063(3) 0.012(2) 0.027(3) 0.012(3) C C19 0.075(3) 0.073(4) 0.053(2) 0.010(3) 0.024(3) 0.014(2) C C20 0.067(3) 0.069(4) 0.044(2) 0.009(3) 0.014(2) 0.015(2) C C21 0.051(2) 0.043(3) 0.037(2) 0.003(2) 0.004(2) 0.005(2) C C22 0.046(2) 0.042(3) 0.033(2) 0.004(2) -0.001(2) 0.007(2) C C23 0.049(2) 0.063(5) 0.046(3) -0.003(2) 0.003(2) 0.024(3) C C24 0.054(2) 0.084(5) 0.062(3) 0.005(3) 0.014(2) 0.034(3) C C25 0.052(2) 0.117(6) 0.096(4) 0.008(3) 0.017(2) 0.054(5) C C26 0.050(2) 0.134(7) 0.106(5) -0.005(2) -0.004(2) 0.059(6) C C27 0.059(2) 0.128(6) 0.076(3) -0.013(3) -0.016(3) 0.038(4) C C28 0.058(2) 0.090(5) 0.050(3) -0.008(3) -0.007(2) 0.024(3) C C29 0.064(3) 0.069(4) 0.030(3) 0.023(3) 0.010(2) 0.019(3) C C30 0.113(4) 0.073(4) 0.055(4) 0.043(3) 0.017(3) 0.030(3) C C31 0.151(7) 0.124(4) 0.071(5) 0.088(5) 0.033(4) 0.055(4) C C32 0.115(5) 0.190(8) 0.060(5) 0.093(6) 0.025(3) 0.064(6) C C33 0.082(4) 0.179(7) 0.064(4) 0.041(4) -0.010(3) 0.044(5) C C34 0.070(4) 0.107(4) 0.050(4) 0.014(3) -0.009(3) 0.023(3) C C1Dcm 0.057(9) 0.277(9) 0.161(6) -0.010(6) 0.051(6) -0.035(7) C Cl1Dcm 0.166(6) 0.235(8) 0.359(9) 0.055(5) 0.126(7) 0.078(5) Cl Cl2Dcm 0.184(8) 0.363(9) 0.169(5) 0.008(6) 0.043(5) 0.082(5) Cl C1Dcm' 0.046(9) 0.229(8) 0.139(6) 0.021(5) 0.036(6) 0.010(6) C Cl1Dcm' 0.163(6) 0.275(7) 0.206(6) 0.019(5) 0.082(4) 0.068(5) Cl Cl2Dcm' 0.149(9) 0.302(9) 0.169(7) -0.051(6) 0.108(7) -0.037(6) Cl # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.993(7) 1_555 1_555 no Br2 C8 1.980(7) 1_555 1_555 no S1 C1 1.814(7) 1_555 1_555 no S1 C5 1.795(8) 1_555 1_555 no N1 C2 1.324(8) 1_555 1_555 no N1 C9 1.349(9) 1_555 1_555 no N2 C6 1.300(8) 1_555 1_555 no N2 C16 1.366(9) 1_555 1_555 no C1 C2 1.517(9) 1_555 1_555 no C1 C8 1.515(9) 1_555 1_555 no C2 C3 1.430(9) 1_555 1_555 no C3 C4 1.505(9) 1_555 1_555 no C3 C15 1.364(9) 1_555 1_555 no C4 C5 1.513(10) 1_555 1_555 no C5 C6 1.534(10) 1_555 1_555 no C6 C7 1.432(9) 1_555 1_555 no C7 C8 1.507(10) 1_555 1_555 no C7 C22 1.388(10) 1_555 1_555 no C9 C10 1.408(10) 1_555 1_555 no C9 C14 1.426(10) 1_555 1_555 no C10 C11 1.365(11) 1_555 1_555 no C11 C12 1.383(13) 1_555 1_555 no C12 C13 1.375(11) 1_555 1_555 no C13 C14 1.432(10) 1_555 1_555 no C14 C15 1.436(10) 1_555 1_555 no C15 C23 1.497(9) 1_555 1_555 no C16 C17 1.401(10) 1_555 1_555 no C16 C21 1.414(10) 1_555 1_555 no C17 C18 1.370(11) 1_555 1_555 no C18 C19 1.373(12) 1_555 1_555 no C19 C20 1.359(11) 1_555 1_555 no C20 C21 1.445(11) 1_555 1_555 no C21 C22 1.416(10) 1_555 1_555 no C22 C29 1.488(9) 1_555 1_555 no C23 C24 1.381(5) 1_555 1_555 no C23 C28 1.381(5) 1_555 1_555 no C24 C25 1.394(6) 1_555 1_555 no C25 C26 1.368(6) 1_555 1_555 no C26 C27 1.368(6) 1_555 1_555 no C27 C28 1.394(6) 1_555 1_555 no C29 C30 1.381(5) 1_555 1_555 no C29 C34 1.381(5) 1_555 1_555 no C30 C31 1.394(6) 1_555 1_555 no C31 C32 1.368(6) 1_555 1_555 no C32 C33 1.368(6) 1_555 1_555 no C33 C34 1.394(6) 1_555 1_555 no C1Dcm Cl1Dcm 1.702(8) 1_555 1_555 no C1Dcm Cl2Dcm 1.702(8) 1_555 1_555 no C1Dcm' Cl1Dcm' 1.702(8) 1_555 1_555 no C1Dcm' Cl2Dcm' 1.702(8) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C5 92.9(3) 1_555 1_555 1_555 no C2 N1 C9 118.3(6) 1_555 1_555 1_555 no C6 N2 C16 119.4(6) 1_555 1_555 1_555 no S1 C1 C2 113.2(5) 1_555 1_555 1_555 no S1 C1 C8 110.9(5) 1_555 1_555 1_555 no C2 C1 C8 108.7(6) 1_555 1_555 1_555 no N1 C2 C1 111.9(6) 1_555 1_555 1_555 no N1 C2 C3 124.2(7) 1_555 1_555 1_555 no C1 C2 C3 123.8(6) 1_555 1_555 1_555 no C2 C3 C4 120.6(6) 1_555 1_555 1_555 no C2 C3 C15 118.0(6) 1_555 1_555 1_555 no C4 C3 C15 121.4(6) 1_555 1_555 1_555 no Br1 C4 C3 108.5(5) 1_555 1_555 1_555 no Br1 C4 C5 109.4(5) 1_555 1_555 1_555 no C3 C4 C5 115.7(6) 1_555 1_555 1_555 no S1 C5 C4 111.8(5) 1_555 1_555 1_555 no S1 C5 C6 114.8(5) 1_555 1_555 1_555 no C4 C5 C6 107.5(6) 1_555 1_555 1_555 no N2 C6 C5 113.9(6) 1_555 1_555 1_555 no N2 C6 C7 123.8(7) 1_555 1_555 1_555 no C5 C6 C7 122.0(6) 1_555 1_555 1_555 no C6 C7 C8 121.6(6) 1_555 1_555 1_555 no C6 C7 C22 118.0(7) 1_555 1_555 1_555 no C8 C7 C22 120.4(6) 1_555 1_555 1_555 no Br2 C8 C1 108.0(5) 1_555 1_555 1_555 no Br2 C8 C7 109.5(5) 1_555 1_555 1_555 no C1 C8 C7 116.1(6) 1_555 1_555 1_555 no N1 C9 C10 118.5(7) 1_555 1_555 1_555 no N1 C9 C14 122.1(7) 1_555 1_555 1_555 no C10 C9 C14 119.4(7) 1_555 1_555 1_555 no C9 C10 C11 120.8(8) 1_555 1_555 1_555 no C10 C11 C12 120.1(8) 1_555 1_555 1_555 no C11 C12 C13 122.0(8) 1_555 1_555 1_555 no C12 C13 C14 119.2(8) 1_555 1_555 1_555 no C9 C14 C13 118.4(7) 1_555 1_555 1_555 no C9 C14 C15 117.9(7) 1_555 1_555 1_555 no C13 C14 C15 123.7(7) 1_555 1_555 1_555 no C3 C15 C14 119.2(7) 1_555 1_555 1_555 no C3 C15 C23 122.3(7) 1_555 1_555 1_555 no C14 C15 C23 118.5(6) 1_555 1_555 1_555 no N2 C16 C17 119.1(7) 1_555 1_555 1_555 no N2 C16 C21 121.0(7) 1_555 1_555 1_555 no C17 C16 C21 119.9(7) 1_555 1_555 1_555 no C16 C17 C18 120.6(8) 1_555 1_555 1_555 no C17 C18 C19 120.5(8) 1_555 1_555 1_555 no C18 C19 C20 121.4(8) 1_555 1_555 1_555 no C19 C20 C21 120.2(8) 1_555 1_555 1_555 no C16 C21 C20 117.4(7) 1_555 1_555 1_555 no C16 C21 C22 119.3(7) 1_555 1_555 1_555 no C20 C21 C22 123.3(7) 1_555 1_555 1_555 no C7 C22 C21 118.4(7) 1_555 1_555 1_555 no C7 C22 C29 121.8(7) 1_555 1_555 1_555 no C21 C22 C29 119.8(6) 1_555 1_555 1_555 no C15 C23 C24 121.1(5) 1_555 1_555 1_555 no C15 C23 C28 119.1(5) 1_555 1_555 1_555 no C24 C23 C28 119.7(6) 1_555 1_555 1_555 no C23 C24 C25 119.8(5) 1_555 1_555 1_555 no C24 C25 C26 120.3(6) 1_555 1_555 1_555 no C25 C26 C27 120.1(7) 1_555 1_555 1_555 no C26 C27 C28 120.3(6) 1_555 1_555 1_555 no C23 C28 C27 119.8(5) 1_555 1_555 1_555 no C22 C29 C30 120.8(6) 1_555 1_555 1_555 no C22 C29 C34 119.5(5) 1_555 1_555 1_555 no C30 C29 C34 119.7(6) 1_555 1_555 1_555 no C29 C30 C31 119.8(5) 1_555 1_555 1_555 no C30 C31 C32 120.3(5) 1_555 1_555 1_555 no C31 C32 C33 120.1(7) 1_555 1_555 1_555 no C32 C33 C34 120.3(6) 1_555 1_555 1_555 no C29 C34 C33 119.8(5) 1_555 1_555 1_555 no Cl1Dcm C1Dcm Cl2Dcm 113.0(8) 1_555 1_555 1_555 no Cl1Dcm' C1Dcm' Cl2Dcm' 113.0(8) 1_555 1_555 1_555 no # Attachment '10_cs2_drb324.cif' data_DRB324 _database_code_depnum_ccdc_archive 'CCDC 659340' _audit_creation_method 'RAELSPUB and manual entry' _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C34 H22 Br2 N2 S,C S2' _chemical_formula_sum 'C35 H22 Br2 N2 S3' _chemical_formula_iupac ? _chemical_formula_weight 726.6 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.964(5) _cell_length_b 10.551(5) _cell_length_c 15.788(8) _cell_angle_alpha 104.96(3) _cell_angle_beta 99.56(3) _cell_angle_gamma 97.30(3) _cell_volume 1556(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11 _cell_measurement_theta_max 13 _cell_measurement_temperature 294 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.55 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728.0 _exptl_absorpt_coefficient_mu 2.810 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.73 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 5622 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 4 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 5402 _reflns_number_gt 3166 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.064 _refine_ls_wR_factor_ref 0.071 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3166 _refine_ls_number_parameters 197 _refine_ls_goodness_of_fit_ref 1.85 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.004 _refine_diff_density_max 1.06 _refine_diff_density_min -1.21 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.41589(11) 0.68554(9) 0.56075(6) 0.0519(3) Uani Br 1.0 Br2 0.95117(11) 0.85042(12) 0.90785(7) 0.0728(4) Uani Br 1.0 S1 0.7192(2) 0.8212(2) 0.7163(2) 0.0415(8) Uani S 1.0 N1 0.7257(7) 0.4463(6) 0.6995(4) 0.036(1) Uani N 1.0 N2 0.4516(7) 0.8292(6) 0.8733(4) 0.037(2) Uani N 1.0 C1 0.7692(8) 0.6804(8) 0.7512(5) 0.037(1) Uani C 1.0 C2 0.6656(8) 0.5511(8) 0.7074(5) 0.032(1) Uani C 1.0 C3 0.5220(8) 0.5445(7) 0.6820(5) 0.029(1) Uani C 1.0 C4 0.4592(8) 0.6690(7) 0.6855(5) 0.0310(9) Uani C 1.0 C5 0.5529(8) 0.7983(8) 0.7463(5) 0.036(1) Uani C 1.0 C6 0.5582(8) 0.7937(7) 0.8424(5) 0.034(1) Uani C 1.0 C7 0.6667(8) 0.7478(7) 0.8913(5) 0.034(1) Uani C 1.0 C8 0.7884(8) 0.7085(8) 0.8518(5) 0.0367(9) Uani C 1.0 C9 0.6421(9) 0.3211(8) 0.6671(5) 0.035(1) Uani C 1.0 C10 0.7084(9) 0.2085(8) 0.6542(5) 0.045(2) Uani C 1.0 C11 0.6295(11) 0.0834(9) 0.6235(6) 0.051(2) Uani C 1.0 C12 0.4857(11) 0.0681(9) 0.6080(6) 0.054(1) Uani C 1.0 C13 0.4191(9) 0.1724(8) 0.6165(6) 0.047(2) Uani C 1.0 C14 0.4978(8) 0.3057(8) 0.6464(5) 0.035(1) Uani C 1.0 C15 0.4349(8) 0.4194(8) 0.6512(5) 0.032(1) Uani C 1.0 C16 0.4406(9) 0.8253(8) 0.9574(6) 0.042(2) Uani C 1.0 C17 0.3306(9) 0.8694(9) 0.9922(6) 0.052(2) Uani C 1.0 C18 0.3150(10) 0.8658(10) 1.0754(7) 0.064(2) Uani C 1.0 C19 0.4146(11) 0.8181(10) 1.1289(6) 0.064(2) Uani C 1.0 C20 0.5244(10) 0.7775(9) 1.0984(6) 0.054(2) Uani C 1.0 C21 0.5433(9) 0.7788(8) 1.0124(6) 0.042(2) Uani C 1.0 C22 0.6562(8) 0.7371(8) 0.9751(5) 0.038(2) Uani C 1.0 C23 0.2837(7) 0.4052(6) 0.6221(4) 0.038(2) Uani C 1.0 C24 0.2008(7) 0.4414(6) 0.6829(4) 0.048(2) Uani C 1.0 C25 0.0603(7) 0.4283(7) 0.6533(6) 0.067(2) Uani C 1.0 C26 0.0011(8) 0.3798(7) 0.5644(5) 0.076(3) Uani C 1.0 C27 0.0828(8) 0.3440(7) 0.5044(5) 0.070(3) Uani C 1.0 C28 0.2236(7) 0.3561(6) 0.5322(4) 0.051(2) Uani C 1.0 C29 0.7629(7) 0.6862(6) 1.0300(4) 0.045(2) Uani C 1.0 C30 0.7603(8) 0.5511(7) 1.0150(5) 0.068(3) Uani C 1.0 C31 0.8627(10) 0.5061(8) 1.0632(6) 0.090(4) Uani C 1.0 C32 0.9673(9) 0.5931(9) 1.1260(5) 0.090(4) Uani C 1.0 C33 0.9700(7) 0.7265(9) 1.1409(4) 0.076(3) Uani C 1.0 C34 0.8689(7) 0.7742(7) 1.0936(4) 0.055(2) Uani C 1.0 S1Cds 0.1913(5) 0.8962(5) 0.7337(3) 0.125(2) Uani S 1.0 S2Cds 0.0279(5) 1.0430(5) 0.6233(3) 0.128(2) Uani S 1.0 C1Cds 0.1086(12) 0.9669(12) 0.6797(8) 0.083(4) Uani C 1.0 HC1 0.8599 0.6665 0.7345 0.040 Uani H 1.0 HC4 0.3708 0.6581 0.7072 0.030 Uani H 1.0 HC5 0.5070 0.8746 0.7381 0.038 Uani H 1.0 HC8 0.8092 0.6261 0.8674 0.035 Uani H 1.0 HC10 0.8116 0.2202 0.6674 0.053 Uani H 1.0 HC11 0.6749 0.0032 0.6122 0.061 Uani H 1.0 HC12 0.4299 -0.0239 0.5898 0.067 Uani H 1.0 HC13 0.3158 0.1575 0.6022 0.057 Uani H 1.0 HC17 0.2612 0.9047 0.9553 0.056 Uani H 1.0 HC18 0.2338 0.8965 1.0989 0.075 Uani H 1.0 HC19 0.4028 0.8148 1.1900 0.076 Uani H 1.0 HC20 0.5940 0.7456 1.1376 0.058 Uani H 1.0 HC24 0.2427 0.4772 0.7484 0.056 Uani H 1.0 HC25 0.0008 0.4547 0.6977 0.088 Uani H 1.0 HC26 -0.1010 0.3706 0.5436 0.101 Uani H 1.0 HC27 0.0399 0.3083 0.4390 0.094 Uani H 1.0 HC28 0.2822 0.3294 0.4872 0.060 Uani H 1.0 HC30 0.6842 0.4859 0.9691 0.087 Uani H 1.0 HC31 0.8602 0.4080 1.0520 0.125 Uani H 1.0 HC32 1.0411 0.5594 1.1607 0.119 Uani H 1.0 HC33 1.0465 0.7909 1.1869 0.102 Uani H 1.0 HC34 0.8724 0.8725 1.1053 0.066 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0672(7) 0.0413(6) 0.0379(6) 0.0069(5) -0.0106(5) 0.0098(4) Br Br2 0.0441(7) 0.0841(9) 0.0624(7) -0.0157(6) -0.0093(5) -0.0015(6) Br S1 0.042(1) 0.035(1) 0.044(1) -0.0003(9) 0.005(1) 0.010(1) S N1 0.034(2) 0.038(2) 0.033(3) 0.012(2) -0.004(2) 0.007(2) N N2 0.027(3) 0.034(3) 0.036(2) 0.000(2) 0.001(2) -0.008(2) N C1 0.033(1) 0.036(2) 0.036(2) 0.0016(9) 0.002(1) 0.007(1) C C2 0.030(2) 0.032(1) 0.029(2) 0.006(1) 0.001(2) 0.005(1) C C3 0.031(2) 0.026(1) 0.027(2) 0.007(1) 0.001(1) 0.004(1) C C4 0.035(1) 0.025(2) 0.030(2) 0.007(1) 0.002(1) 0.005(2) C C5 0.041(1) 0.025(1) 0.036(2) 0.004(1) 0.003(1) 0.006(1) C C6 0.038(2) 0.023(2) 0.034(2) 0.003(1) 0.000(2) 0.002(1) C C7 0.034(2) 0.027(2) 0.033(1) 0.001(2) -0.002(2) 0.000(2) C C8 0.032(2) 0.034(2) 0.035(2) 0.000(1) -0.001(1) 0.002(2) C C9 0.042(2) 0.034(2) 0.028(2) 0.014(2) 0.002(2) 0.007(1) C C10 0.058(2) 0.040(2) 0.037(3) 0.024(2) 0.005(3) 0.010(2) C C11 0.079(4) 0.036(2) 0.041(4) 0.024(2) 0.008(4) 0.010(2) C C12 0.077(4) 0.030(2) 0.050(4) 0.009(2) 0.005(4) 0.009(2) C C13 0.056(2) 0.031(2) 0.049(4) 0.002(2) 0.004(3) 0.010(2) C C14 0.041(2) 0.030(2) 0.031(3) 0.007(2) 0.003(2) 0.007(2) C C15 0.032(3) 0.031(2) 0.031(3) 0.005(2) 0.003(2) 0.007(2) C C16 0.032(2) 0.041(3) 0.039(2) -0.001(2) 0.006(2) -0.006(2) C C17 0.036(2) 0.058(4) 0.050(3) 0.001(2) 0.013(2) -0.006(3) C C18 0.049(3) 0.075(5) 0.055(3) 0.000(3) 0.023(3) -0.003(3) C C19 0.061(4) 0.074(5) 0.048(2) -0.004(3) 0.022(3) 0.003(3) C C20 0.056(4) 0.056(4) 0.040(2) -0.004(3) 0.012(2) 0.003(2) C C21 0.040(2) 0.040(3) 0.036(2) -0.003(2) 0.005(2) -0.002(2) C C22 0.038(3) 0.031(3) 0.033(3) -0.001(2) 0.000(2) -0.003(2) C C23 0.036(3) 0.029(4) 0.045(3) 0.005(2) 0.001(2) 0.012(3) C C24 0.040(3) 0.047(4) 0.062(3) 0.010(2) 0.013(2) 0.022(3) C C25 0.039(3) 0.069(5) 0.103(5) 0.013(3) 0.018(3) 0.041(5) C C26 0.036(3) 0.077(6) 0.115(6) -0.001(2) -0.008(2) 0.049(5) C C27 0.050(3) 0.067(5) 0.078(4) -0.011(3) -0.022(3) 0.027(4) C C28 0.049(3) 0.042(4) 0.049(3) -0.003(2) -0.009(2) 0.009(3) C C29 0.051(4) 0.049(4) 0.033(3) 0.010(3) 0.003(3) 0.010(3) C C30 0.089(5) 0.052(3) 0.063(4) 0.018(3) 0.010(3) 0.021(3) C C31 0.125(8) 0.087(4) 0.079(6) 0.055(5) 0.025(4) 0.043(4) C C32 0.101(6) 0.135(7) 0.058(5) 0.069(6) 0.018(4) 0.047(5) C C33 0.066(4) 0.122(6) 0.040(4) 0.035(4) -0.004(3) 0.020(4) C C34 0.053(4) 0.070(3) 0.032(3) 0.012(3) -0.004(3) 0.006(3) C S1Cds 0.126(4) 0.159(4) 0.102(3) 0.074(3) 0.021(3) 0.039(3) S S2Cds 0.125(4) 0.131(4) 0.136(4) 0.051(3) 0.018(3) 0.046(3) S C1Cds 0.068(8) 0.092(9) 0.077(9) 0.019(7) 0.022(7) -0.001(7) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 2.002(7) 1_555 1_555 no Br2 C8 1.969(8) 1_555 1_555 no S1 C1 1.810(8) 1_555 1_555 no S1 C5 1.802(8) 1_555 1_555 no N1 C2 1.311(9) 1_555 1_555 no N1 C9 1.390(9) 1_555 1_555 no N2 C6 1.298(9) 1_555 1_555 no N2 C16 1.361(10) 1_555 1_555 no C1 C2 1.524(10) 1_555 1_555 no C1 C8 1.513(10) 1_555 1_555 no C2 C3 1.408(10) 1_555 1_555 no C3 C4 1.519(10) 1_555 1_555 no C3 C15 1.403(10) 1_555 1_555 no C4 C5 1.535(10) 1_555 1_555 no C5 C6 1.523(11) 1_555 1_555 no C6 C7 1.432(10) 1_555 1_555 no C7 C8 1.508(11) 1_555 1_555 no C7 C22 1.376(11) 1_555 1_555 no C9 C10 1.417(11) 1_555 1_555 no C9 C14 1.399(11) 1_555 1_555 no C10 C11 1.368(11) 1_555 1_555 no C11 C12 1.394(13) 1_555 1_555 no C12 C13 1.345(11) 1_555 1_555 no C13 C14 1.438(11) 1_555 1_555 no C14 C15 1.413(10) 1_555 1_555 no C15 C23 1.477(10) 1_555 1_555 no C16 C17 1.385(11) 1_555 1_555 no C16 C21 1.448(11) 1_555 1_555 no C17 C18 1.358(12) 1_555 1_555 no C18 C19 1.422(14) 1_555 1_555 no C19 C20 1.341(12) 1_555 1_555 no C20 C21 1.405(11) 1_555 1_555 no C21 C22 1.420(11) 1_555 1_555 no C22 C29 1.500(10) 1_555 1_555 no C23 C24 1.379(5) 1_555 1_555 no C23 C28 1.379(5) 1_555 1_555 no C24 C25 1.378(7) 1_555 1_555 no C25 C26 1.362(6) 1_555 1_555 no C26 C27 1.362(6) 1_555 1_555 no C27 C28 1.378(7) 1_555 1_555 no C29 C30 1.379(5) 1_555 1_555 no C29 C34 1.379(5) 1_555 1_555 no C30 C31 1.378(7) 1_555 1_555 no C31 C32 1.362(6) 1_555 1_555 no C32 C33 1.362(6) 1_555 1_555 no C33 C34 1.378(7) 1_555 1_555 no S1Cds C1Cds 1.487(13) 1_555 1_555 no S2Cds C1Cds 1.543(13) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C5 93.1(4) 1_555 1_555 1_555 no C2 N1 C9 118.0(7) 1_555 1_555 1_555 no C6 N2 C16 119.5(7) 1_555 1_555 1_555 no S1 C1 C2 113.6(5) 1_555 1_555 1_555 no S1 C1 C8 110.7(6) 1_555 1_555 1_555 no C2 C1 C8 108.2(6) 1_555 1_555 1_555 no N1 C2 C1 111.8(7) 1_555 1_555 1_555 no N1 C2 C3 124.0(7) 1_555 1_555 1_555 no C1 C2 C3 124.2(7) 1_555 1_555 1_555 no C2 C3 C4 121.7(7) 1_555 1_555 1_555 no C2 C3 C15 119.2(7) 1_555 1_555 1_555 no C4 C3 C15 119.1(7) 1_555 1_555 1_555 no Br1 C4 C3 108.0(5) 1_555 1_555 1_555 no Br1 C4 C5 108.5(5) 1_555 1_555 1_555 no C3 C4 C5 114.3(6) 1_555 1_555 1_555 no S1 C5 C4 111.7(6) 1_555 1_555 1_555 no S1 C5 C6 114.7(6) 1_555 1_555 1_555 no C4 C5 C6 106.6(6) 1_555 1_555 1_555 no N2 C6 C5 113.2(7) 1_555 1_555 1_555 no N2 C6 C7 123.8(8) 1_555 1_555 1_555 no C5 C6 C7 122.8(7) 1_555 1_555 1_555 no C6 C7 C8 121.3(7) 1_555 1_555 1_555 no C6 C7 C22 118.3(8) 1_555 1_555 1_555 no C8 C7 C22 120.3(7) 1_555 1_555 1_555 no Br2 C8 C1 108.1(5) 1_555 1_555 1_555 no Br2 C8 C7 109.2(5) 1_555 1_555 1_555 no C1 C8 C7 116.0(7) 1_555 1_555 1_555 no N1 C9 C10 117.6(8) 1_555 1_555 1_555 no N1 C9 C14 121.6(7) 1_555 1_555 1_555 no C10 C9 C14 120.8(8) 1_555 1_555 1_555 no C9 C10 C11 119.3(8) 1_555 1_555 1_555 no C10 C11 C12 119.9(8) 1_555 1_555 1_555 no C11 C12 C13 122.5(9) 1_555 1_555 1_555 no C12 C13 C14 119.5(9) 1_555 1_555 1_555 no C9 C14 C13 117.9(8) 1_555 1_555 1_555 no C9 C14 C15 119.6(7) 1_555 1_555 1_555 no C13 C14 C15 122.4(8) 1_555 1_555 1_555 no C3 C15 C14 117.4(7) 1_555 1_555 1_555 no C3 C15 C23 122.0(7) 1_555 1_555 1_555 no C14 C15 C23 120.6(7) 1_555 1_555 1_555 no N2 C16 C17 119.6(8) 1_555 1_555 1_555 no N2 C16 C21 121.4(8) 1_555 1_555 1_555 no C17 C16 C21 119.0(8) 1_555 1_555 1_555 no C16 C17 C18 121.4(9) 1_555 1_555 1_555 no C17 C18 C19 119.6(9) 1_555 1_555 1_555 no C18 C19 C20 120.8(9) 1_555 1_555 1_555 no C19 C20 C21 121.2(9) 1_555 1_555 1_555 no C16 C21 C20 118.0(8) 1_555 1_555 1_555 no C16 C21 C22 117.3(8) 1_555 1_555 1_555 no C20 C21 C22 124.6(9) 1_555 1_555 1_555 no C7 C22 C21 119.5(8) 1_555 1_555 1_555 no C7 C22 C29 122.0(7) 1_555 1_555 1_555 no C21 C22 C29 118.5(7) 1_555 1_555 1_555 no C15 C23 C24 121.5(6) 1_555 1_555 1_555 no C15 C23 C28 119.5(6) 1_555 1_555 1_555 no C24 C23 C28 119.0(6) 1_555 1_555 1_555 no C23 C24 C25 119.9(5) 1_555 1_555 1_555 no C24 C25 C26 121.0(6) 1_555 1_555 1_555 no C25 C26 C27 119.1(7) 1_555 1_555 1_555 no C26 C27 C28 121.0(6) 1_555 1_555 1_555 no C23 C28 C27 119.9(5) 1_555 1_555 1_555 no C22 C29 C30 120.7(6) 1_555 1_555 1_555 no C22 C29 C34 120.3(6) 1_555 1_555 1_555 no C30 C29 C34 119.0(6) 1_555 1_555 1_555 no C29 C30 C31 119.9(5) 1_555 1_555 1_555 no C30 C31 C32 121.0(6) 1_555 1_555 1_555 no C31 C32 C33 119.1(7) 1_555 1_555 1_555 no C32 C33 C34 121.0(6) 1_555 1_555 1_555 no C29 C34 C33 119.9(5) 1_555 1_555 1_555 no S1Cds C1Cds S2Cds 177.9(9) 1_555 1_555 1_555 no # Attachment '10_drb322.cif' data_DRB322 _database_code_depnum_ccdc_archive 'CCDC 659341' _audit_creation_method 'RAELSPUB and manual entry' _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C34 H22 Br2 N2 S' _chemical_formula_sum 'C34 H22 Br2 N2 S' _chemical_formula_iupac ? _chemical_formula_weight 650.4 # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 -x,-y,-z 4 -x,y,1/2-z 5 1/2+x,1/2+y,z 6 1/2+x,1/2-y,1/2+z 7 1/2-x,1/2-y,-z 8 1/2-x,1/2+y,1/2-z _cell_length_a 21.421(8) _cell_length_b 8.159(1) _cell_length_c 17.182(6) _cell_angle_alpha 90 _cell_angle_beta 116.29(2) _cell_angle_gamma 90 _cell_volume 2692(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_size_rad 0.1 _exptl_crystal_density_diffrn 1.60 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304.0 _exptl_absorpt_coefficient_mu 3.089 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 2465 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 2375 _reflns_number_gt 1795 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.047 _refine_ls_wR_factor_ref 0.073 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1795 _refine_ls_number_parameters 146 _refine_ls_goodness_of_fit_ref 1.75 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.005 _refine_diff_density_max 0.72 _refine_diff_density_min -0.73 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.32503(3) 0.56369(10) 0.15421(4) 0.0637(3) Uani Br 1.0 S1 0.5000 0.6624(3) 0.2500 0.0427(5) Uani S 1.0 N1 0.5075(2) 0.3521(6) 0.4240(3) 0.032(1) Uani N 1.0 C1 0.5410(3) 0.5093(7) 0.3335(3) 0.034(1) Uani C 1.0 C2 0.4885(3) 0.3949(6) 0.3430(3) 0.031(1) Uani C 1.0 C3 0.4262(3) 0.3435(7) 0.2715(3) 0.029(1) Uani C 1.0 C4 0.4039(3) 0.4120(7) 0.1807(3) 0.034(1) Uani C 1.0 C5 0.4656(3) 0.2500(6) 0.4410(3) 0.030(1) Uani C 1.0 C6 0.4846(3) 0.2064(7) 0.5283(3) 0.038(1) Uani C 1.0 C7 0.4448(3) 0.0997(7) 0.5481(3) 0.041(1) Uani C 1.0 C8 0.3845(3) 0.0303(8) 0.4830(4) 0.045(2) Uani C 1.0 C9 0.3639(3) 0.0707(7) 0.3975(4) 0.039(1) Uani C 1.0 C10 0.4038(3) 0.1816(7) 0.3742(3) 0.032(1) Uani C 1.0 C11 0.3848(3) 0.2319(7) 0.2872(3) 0.032(1) Uani C 1.0 C12 0.3198(3) 0.1628(5) 0.2160(3) 0.037(1) Uani C 1.0 C13 0.3235(3) 0.0477(6) 0.1590(3) 0.049(1) Uani C 1.0 C14 0.2635(3) -0.0181(7) 0.0948(3) 0.063(2) Uani C 1.0 C15 0.1995(3) 0.0299(7) 0.0869(4) 0.065(2) Uani C 1.0 C16 0.1953(2) 0.1440(8) 0.1432(4) 0.062(1) Uani C 1.0 C17 0.2550(2) 0.2105(6) 0.2075(3) 0.048(1) Uani C 1.0 HC1 0.5657 0.5690 0.3898 0.034 Uani H 1.0 HC4 0.3877 0.3193 0.1382 0.034 Uani H 1.0 HC6 0.5275 0.2543 0.5759 0.038 Uani H 1.0 HC7 0.4589 0.0704 0.6101 0.041 Uani H 1.0 HC8 0.3564 -0.0488 0.4989 0.045 Uani H 1.0 HC9 0.3205 0.0217 0.3514 0.039 Uani H 1.0 HC13 0.3700 0.0122 0.1644 0.060 Uani H 1.0 HC14 0.2666 -0.1012 0.0538 0.084 Uani H 1.0 HC15 0.1561 -0.0181 0.0403 0.081 Uani H 1.0 HC16 0.1487 0.1790 0.1374 0.082 Uani H 1.0 HC17 0.2516 0.2935 0.2483 0.058 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0475(4) 0.0868(6) 0.0642(5) 0.0289(4) 0.0313(4) 0.0219(4) Br S1 0.051(1) 0.037(1) 0.043(1) 0.0000 0.022(1) 0.0000 S N1 0.031(2) 0.039(3) 0.028(2) 0.002(2) 0.014(2) -0.003(2) N C1 0.028(3) 0.046(3) 0.029(3) -0.004(2) 0.015(2) -0.006(3) C C2 0.027(3) 0.036(3) 0.034(3) 0.003(2) 0.017(2) -0.004(2) C C3 0.026(3) 0.037(3) 0.029(3) 0.004(2) 0.015(2) -0.002(2) C C4 0.028(3) 0.039(3) 0.034(3) 0.010(2) 0.014(2) 0.004(3) C C5 0.026(3) 0.034(3) 0.033(3) 0.004(2) 0.017(2) 0.002(2) C C6 0.038(3) 0.047(4) 0.031(3) -0.001(3) 0.016(3) -0.007(3) C C7 0.052(4) 0.046(4) 0.035(3) 0.001(3) 0.027(3) 0.003(3) C C8 0.043(3) 0.056(4) 0.045(3) -0.007(3) 0.028(3) -0.002(3) C C9 0.026(3) 0.047(4) 0.046(3) -0.002(3) 0.018(3) 0.001(3) C C10 0.029(3) 0.040(3) 0.031(3) 0.004(2) 0.016(2) -0.002(3) C C11 0.025(3) 0.039(3) 0.037(3) 0.004(2) 0.017(2) -0.001(3) C C12 0.027(1) 0.047(2) 0.036(2) 0.002(1) 0.013(1) 0.002(2) C C13 0.045(2) 0.058(3) 0.043(2) -0.004(2) 0.017(1) -0.009(2) C C14 0.061(2) 0.071(3) 0.046(2) -0.017(2) 0.013(2) -0.011(2) C C15 0.047(2) 0.079(3) 0.047(2) -0.021(2) 0.003(2) 0.006(2) C C16 0.028(1) 0.084(4) 0.059(3) -0.006(1) 0.007(1) 0.010(2) C C17 0.024(1) 0.065(3) 0.051(2) 0.003(1) 0.013(1) 0.004(2) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.977(5) 1_555 1_555 no S1 C1 1.809(6) 1_555 1_555 no S1 C1 1.809(6) 1_555 4_655 no N1 C2 1.313(6) 1_555 1_555 no N1 C5 1.349(6) 1_555 1_555 no C1 C2 1.525(7) 1_555 1_555 no C1 C4 1.528(7) 1_555 4_655 no C2 C3 1.419(7) 1_555 1_555 no C3 C4 1.521(7) 1_555 1_555 no C3 C11 1.379(7) 1_555 1_555 no C4 C1 1.528(7) 1_555 4_655 no C5 C6 1.416(7) 1_555 1_555 no C5 C10 1.426(7) 1_555 1_555 no C6 C7 1.361(8) 1_555 1_555 no C7 C8 1.399(8) 1_555 1_555 no C8 C9 1.374(8) 1_555 1_555 no C9 C10 1.419(7) 1_555 1_555 no C10 C11 1.424(7) 1_555 1_555 no C11 C12 1.499(7) 1_555 1_555 no C12 C13 1.385(5) 1_555 1_555 no C12 C17 1.385(5) 1_555 1_555 no C13 C14 1.379(6) 1_555 1_555 no C14 C15 1.374(6) 1_555 1_555 no C15 C16 1.374(6) 1_555 1_555 no C16 C17 1.379(6) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C1 92.7(4) 1_555 1_555 4_655 no C2 N1 C5 118.1(4) 1_555 1_555 1_555 no S1 C1 C2 112.7(4) 1_555 1_555 1_555 no S1 C1 C4 111.8(4) 1_555 1_555 4_655 no C2 C1 C4 110.9(4) 1_555 1_555 4_655 no N1 C2 C1 112.3(4) 1_555 1_555 1_555 no N1 C2 C3 124.8(5) 1_555 1_555 1_555 no C1 C2 C3 122.9(5) 1_555 1_555 1_555 no C2 C3 C4 121.8(5) 1_555 1_555 1_555 no C2 C3 C11 117.7(5) 1_555 1_555 1_555 no C4 C3 C11 120.4(5) 1_555 1_555 1_555 no Br1 C4 C1 106.2(4) 1_555 1_555 4_655 no Br1 C4 C3 108.3(3) 1_555 1_555 1_555 no C1 C4 C3 116.1(4) 4_655 1_555 1_555 no N1 C5 C6 118.6(5) 1_555 1_555 1_555 no N1 C5 C10 122.5(4) 1_555 1_555 1_555 no C6 C5 C10 118.9(5) 1_555 1_555 1_555 no C5 C6 C7 120.5(5) 1_555 1_555 1_555 no C6 C7 C8 121.2(5) 1_555 1_555 1_555 no C7 C8 C9 120.2(5) 1_555 1_555 1_555 no C8 C9 C10 120.4(5) 1_555 1_555 1_555 no C5 C10 C9 118.9(5) 1_555 1_555 1_555 no C5 C10 C11 117.6(5) 1_555 1_555 1_555 no C9 C10 C11 123.5(5) 1_555 1_555 1_555 no C3 C11 C10 119.1(5) 1_555 1_555 1_555 no C3 C11 C12 122.3(5) 1_555 1_555 1_555 no C10 C11 C12 118.6(5) 1_555 1_555 1_555 no C11 C12 C13 120.6(4) 1_555 1_555 1_555 no C11 C12 C17 120.4(4) 1_555 1_555 1_555 no C13 C12 C17 119.1(5) 1_555 1_555 1_555 no C12 C13 C14 120.3(4) 1_555 1_555 1_555 no C13 C14 C15 120.2(5) 1_555 1_555 1_555 no C14 C15 C16 119.9(6) 1_555 1_555 1_555 no C15 C16 C17 120.2(5) 1_555 1_555 1_555 no C12 C17 C16 120.3(4) 1_555 1_555 1_555 no # Attachment '9_4193.cif' data_4193 _database_code_depnum_ccdc_archive 'CCDC 659342' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H24 N2 S' _chemical_formula_weight 492.61 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7356(15) _cell_length_b 26.301(4) _cell_length_c 10.4093(18) _cell_angle_alpha 90.00 _cell_angle_beta 109.840(4) _cell_angle_gamma 90.00 _cell_volume 2507.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 673 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 29.67 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 17399 _diffrn_reflns_av_R_equivalents 0.0935 _diffrn_reflns_av_sigmaI/netI 0.1176 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5766 _reflns_number_gt 2332 _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^)+(0.0592P)^2^+0.0000P] 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 5766 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1687 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1523 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _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 0.74455(10) 0.60146(3) 0.43239(9) 0.0625(3) Uani 1 1 d . . . N1 N 0.5287(2) 0.62201(9) 0.6763(3) 0.0499(6) Uani 1 1 d . . . N2 N 1.1141(3) 0.55424(9) 0.6837(3) 0.0592(7) Uani 1 1 d . . . C1 C 0.7605(3) 0.68979(11) 0.7959(3) 0.0468(7) Uani 1 1 d . . . C2 C 0.6286(3) 0.69395(10) 0.8265(3) 0.0476(7) Uani 1 1 d . . . C3 C 0.6046(4) 0.73189(12) 0.9134(3) 0.0589(9) Uani 1 1 d . . . H3 H 0.6773 0.7555 0.9544 0.071 Uiso 1 1 calc R . . C4 C 0.4739(4) 0.73373(13) 0.9373(4) 0.0686(10) Uani 1 1 d . . . H4 H 0.4587 0.7584 0.9952 0.082 Uiso 1 1 calc R . . C5 C 0.3640(4) 0.69850(13) 0.8742(4) 0.0651(9) Uani 1 1 d . . . H5 H 0.2757 0.7002 0.8902 0.078 Uiso 1 1 calc R . . C6 C 0.3835(3) 0.66197(12) 0.7905(3) 0.0588(9) Uani 1 1 d . . . H6 H 0.3092 0.6387 0.7504 0.071 Uiso 1 1 calc R . . C7 C 0.5160(3) 0.65897(11) 0.7636(3) 0.0474(8) Uani 1 1 d . . . C8 C 0.6519(3) 0.61977(10) 0.6487(3) 0.0452(7) Uani 1 1 d . . . C9 C 0.6516(3) 0.57914(10) 0.5453(3) 0.0488(8) Uani 1 1 d . . . H9 H 0.5494 0.5737 0.4887 0.059 Uiso 1 1 calc R . . C10 C 0.7112(3) 0.52763(11) 0.6077(3) 0.0562(9) Uani 1 1 d . . . H10A H 0.6716 0.5203 0.6795 0.067 Uiso 1 1 calc R . . H10B H 0.6746 0.5018 0.5378 0.067 Uiso 1 1 calc R . . C11 C 0.8758(3) 0.52237(11) 0.6670(3) 0.0482(8) Uani 1 1 d . . . C12 C 0.9372(3) 0.47995(11) 0.7444(3) 0.0507(8) Uani 1 1 d . . . C13 C 1.0920(3) 0.47416(12) 0.7922(3) 0.0563(8) Uani 1 1 d . . . C14 C 1.1667(4) 0.43225(13) 0.8730(4) 0.0726(10) Uani 1 1 d . . . H14 H 1.1142 0.4072 0.8991 0.087 Uiso 1 1 calc R . . C15 C 1.3146(4) 0.42893(16) 0.9118(4) 0.0854(12) Uani 1 1 d . . . H15 H 1.3621 0.4014 0.9645 0.102 Uiso 1 1 calc R . . C16 C 1.3965(4) 0.46581(17) 0.8743(4) 0.0871(13) Uani 1 1 d . . . H16 H 1.4974 0.4624 0.9013 0.105 Uiso 1 1 calc R . . C17 C 1.3301(4) 0.50690(14) 0.7984(4) 0.0772(11) Uani 1 1 d . . . H17 H 1.3857 0.5314 0.7740 0.093 Uiso 1 1 calc R . . C18 C 1.1771(3) 0.51222(12) 0.7569(3) 0.0591(9) Uani 1 1 d . . . C19 C 0.9709(3) 0.55899(11) 0.6429(3) 0.0502(8) Uani 1 1 d . . . C20 C 0.9177(3) 0.60814(11) 0.5710(3) 0.0532(8) Uani 1 1 d . . . H20 H 0.9897 0.6187 0.5295 0.064 Uiso 1 1 calc R . . C21 C 0.9091(3) 0.65099(10) 0.6674(4) 0.0566(9) Uani 1 1 d . . . H21A H 0.9931 0.6481 0.7504 0.068 Uiso 1 1 calc R . . H21B H 0.9175 0.6831 0.6249 0.068 Uiso 1 1 calc R . . C22 C 0.7727(3) 0.65296(10) 0.7070(3) 0.0460(7) Uani 1 1 d . . . C23 C 0.8833(3) 0.72563(10) 0.8588(3) 0.0469(8) Uani 1 1 d . . . C24 C 0.9915(3) 0.71443(11) 0.9809(3) 0.0532(8) Uani 1 1 d . . . H24 H 0.9863 0.6843 1.0260 0.064 Uiso 1 1 calc R . . C25 C 1.1080(3) 0.74725(13) 1.0377(4) 0.0621(9) Uani 1 1 d . . . H25 H 1.1795 0.7393 1.1206 0.074 Uiso 1 1 calc R . . C26 C 1.1174(4) 0.79148(12) 0.9711(4) 0.0624(9) Uani 1 1 d . . . H26 H 1.1965 0.8132 1.0078 0.075 Uiso 1 1 calc R . . C27 C 1.0102(4) 0.80356(13) 0.8508(4) 0.0682(10) Uani 1 1 d . . . H27 H 1.0160 0.8336 0.8058 0.082 Uiso 1 1 calc R . . C28 C 0.8933(4) 0.77110(12) 0.7961(4) 0.0629(9) Uani 1 1 d . . . H28 H 0.8198 0.7800 0.7154 0.075 Uiso 1 1 calc R . . C29 C 0.8441(3) 0.44041(11) 0.7759(4) 0.0533(8) Uani 1 1 d . . . C30 C 0.8364(4) 0.43612(12) 0.9055(4) 0.0648(9) Uani 1 1 d . . . H30 H 0.8915 0.4577 0.9745 0.078 Uiso 1 1 calc R . . C31 C 0.7478(4) 0.40013(13) 0.9330(4) 0.0749(10) Uani 1 1 d . . . H31 H 0.7440 0.3975 1.0208 0.090 Uiso 1 1 calc R . . C32 C 0.6647(4) 0.36803(13) 0.8321(5) 0.0717(11) Uani 1 1 d . . . H32 H 0.6038 0.3441 0.8510 0.086 Uiso 1 1 calc R . . C33 C 0.6728(4) 0.37177(12) 0.7037(4) 0.0662(10) Uani 1 1 d . . . H33 H 0.6180 0.3498 0.6356 0.079 Uiso 1 1 calc R . . C34 C 0.7612(3) 0.40783(11) 0.6734(4) 0.0576(9) Uani 1 1 d . . . H34 H 0.7651 0.4102 0.5856 0.069 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 0.0699(6) 0.0611(5) 0.0589(6) -0.0006(5) 0.0248(5) 0.0030(5) N1 0.0426(15) 0.0441(14) 0.0638(18) 0.0031(13) 0.0192(13) -0.0010(11) N2 0.0477(16) 0.0474(16) 0.086(2) -0.0126(15) 0.0268(15) -0.0001(13) C1 0.0406(17) 0.0458(17) 0.056(2) 0.0013(15) 0.0187(15) -0.0027(14) C2 0.0491(18) 0.0419(17) 0.054(2) 0.0026(15) 0.0198(16) 0.0041(15) C3 0.059(2) 0.058(2) 0.064(2) -0.0062(18) 0.0271(18) 0.0017(17) C4 0.073(2) 0.065(2) 0.082(3) -0.002(2) 0.044(2) 0.011(2) C5 0.058(2) 0.070(2) 0.080(3) 0.008(2) 0.040(2) 0.0072(19) C6 0.0483(19) 0.062(2) 0.068(2) 0.0081(18) 0.0231(18) 0.0066(16) C7 0.0418(17) 0.0474(18) 0.057(2) 0.0063(16) 0.0214(16) 0.0021(15) C8 0.0389(17) 0.0412(17) 0.055(2) 0.0085(15) 0.0146(15) 0.0039(13) C9 0.0370(16) 0.0437(17) 0.061(2) -0.0018(15) 0.0108(15) -0.0013(13) C10 0.0459(18) 0.0422(17) 0.078(2) -0.0008(17) 0.0179(17) 0.0002(14) C11 0.0463(18) 0.0410(17) 0.057(2) -0.0032(15) 0.0166(15) -0.0007(14) C12 0.0508(19) 0.0457(18) 0.055(2) -0.0107(16) 0.0169(16) 0.0000(15) C13 0.049(2) 0.056(2) 0.058(2) -0.0110(17) 0.0102(17) 0.0084(17) C14 0.069(2) 0.076(2) 0.062(2) -0.004(2) 0.009(2) 0.020(2) C15 0.074(3) 0.085(3) 0.075(3) -0.009(2) -0.002(2) 0.030(2) C16 0.050(2) 0.088(3) 0.102(3) -0.030(3) -0.002(2) 0.016(2) C17 0.046(2) 0.073(3) 0.104(3) -0.033(2) 0.014(2) -0.0003(18) C18 0.0456(19) 0.054(2) 0.073(2) -0.0209(19) 0.0138(18) 0.0015(17) C19 0.0458(19) 0.0441(18) 0.064(2) -0.0090(16) 0.0232(17) -0.0010(15) C20 0.0476(18) 0.0495(18) 0.068(2) -0.0037(17) 0.0270(17) -0.0041(15) C21 0.0513(19) 0.0452(17) 0.085(2) -0.0069(17) 0.0378(18) -0.0056(15) C22 0.0408(17) 0.0424(17) 0.057(2) 0.0000(15) 0.0195(15) -0.0008(14) C23 0.0451(18) 0.0394(17) 0.060(2) -0.0037(16) 0.0231(17) -0.0022(14) C24 0.0496(19) 0.0434(17) 0.065(2) 0.0009(16) 0.0177(18) 0.0014(15) C25 0.052(2) 0.060(2) 0.070(2) -0.0082(19) 0.0146(18) 0.0025(17) C26 0.054(2) 0.057(2) 0.082(3) -0.019(2) 0.031(2) -0.0124(17) C27 0.076(2) 0.056(2) 0.074(3) -0.006(2) 0.027(2) -0.022(2) C28 0.064(2) 0.054(2) 0.064(2) 0.0007(18) 0.0145(19) -0.0061(18) C29 0.053(2) 0.0414(18) 0.064(2) -0.0004(17) 0.0182(18) 0.0061(15) C30 0.077(2) 0.055(2) 0.067(3) -0.0017(19) 0.031(2) -0.0012(19) C31 0.089(3) 0.062(2) 0.085(3) 0.011(2) 0.045(2) 0.006(2) C32 0.062(2) 0.054(2) 0.104(3) 0.018(2) 0.034(2) 0.0041(18) C33 0.059(2) 0.0420(19) 0.092(3) 0.0008(19) 0.018(2) 0.0053(16) C34 0.062(2) 0.0427(19) 0.067(2) 0.0014(17) 0.0211(18) 0.0069(16) _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 C9 1.807(3) . ? S1 C20 1.817(3) . ? N1 C8 1.326(3) . ? N1 C7 1.365(3) . ? N2 C19 1.319(3) . ? N2 C18 1.364(4) . ? C1 C22 1.373(4) . ? C1 C2 1.429(4) . ? C1 C23 1.488(4) . ? C2 C7 1.410(4) . ? C2 C3 1.418(4) . ? C3 C4 1.378(4) . ? C4 C5 1.399(4) . ? C5 C6 1.353(4) . ? C6 C7 1.412(4) . ? C8 C22 1.424(4) . ? C8 C9 1.516(4) . ? C9 C10 1.530(4) . ? C10 C11 1.515(4) . ? C11 C12 1.387(4) . ? C11 C19 1.416(4) . ? C12 C13 1.426(4) . ? C12 C29 1.488(4) . ? C13 C18 1.424(4) . ? C13 C14 1.427(4) . ? C14 C15 1.360(5) . ? C15 C16 1.393(5) . ? C16 C17 1.365(5) . ? C17 C18 1.410(4) . ? C19 C20 1.496(4) . ? C20 C21 1.530(4) . ? C21 C22 1.519(4) . ? C23 C24 1.379(4) . ? C23 C28 1.382(4) . ? C24 C25 1.388(4) . ? C25 C26 1.373(4) . ? C26 C27 1.369(4) . ? C27 C28 1.381(4) . ? C29 C30 1.380(4) . ? C29 C34 1.393(4) . ? C30 C31 1.375(4) . ? C31 C32 1.376(5) . ? C32 C33 1.369(5) . ? C33 C34 1.387(4) . ? 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 C9 S1 C20 92.84(14) . . ? C8 N1 C7 118.0(2) . . ? C19 N2 C18 118.8(3) . . ? C22 C1 C2 119.6(3) . . ? C22 C1 C23 120.2(3) . . ? C2 C1 C23 120.1(3) . . ? C7 C2 C3 119.0(3) . . ? C7 C2 C1 117.5(3) . . ? C3 C2 C1 123.4(3) . . ? C4 C3 C2 120.1(3) . . ? C3 C4 C5 119.9(3) . . ? C6 C5 C4 121.4(3) . . ? C5 C6 C7 120.3(3) . . ? N1 C7 C2 122.8(3) . . ? N1 C7 C6 117.8(3) . . ? C2 C7 C6 119.4(3) . . ? N1 C8 C22 123.9(3) . . ? N1 C8 C9 113.7(2) . . ? C22 C8 C9 122.5(3) . . ? C8 C9 C10 114.4(3) . . ? C8 C9 S1 110.61(19) . . ? C10 C9 S1 111.2(2) . . ? C11 C10 C9 116.8(2) . . ? C12 C11 C19 118.1(3) . . ? C12 C11 C10 119.8(3) . . ? C19 C11 C10 122.0(3) . . ? C11 C12 C13 119.0(3) . . ? C11 C12 C29 121.1(3) . . ? C13 C12 C29 119.9(3) . . ? C18 C13 C12 118.2(3) . . ? C18 C13 C14 118.1(3) . . ? C12 C13 C14 123.7(3) . . ? C15 C14 C13 120.1(4) . . ? C14 C15 C16 121.4(4) . . ? C17 C16 C15 120.6(4) . . ? C16 C17 C18 120.0(4) . . ? N2 C18 C17 118.6(3) . . ? N2 C18 C13 121.5(3) . . ? C17 C18 C13 119.8(3) . . ? N2 C19 C11 124.2(3) . . ? N2 C19 C20 113.1(3) . . ? C11 C19 C20 122.7(3) . . ? C19 C20 C21 113.3(3) . . ? C19 C20 S1 112.6(2) . . ? C21 C20 S1 110.5(2) . . ? C22 C21 C20 116.8(2) . . ? C1 C22 C8 118.2(3) . . ? C1 C22 C21 119.4(3) . . ? C8 C22 C21 122.3(3) . . ? C24 C23 C28 117.8(3) . . ? C24 C23 C1 121.2(3) . . ? C28 C23 C1 121.0(3) . . ? C23 C24 C25 121.2(3) . . ? C26 C25 C24 119.8(3) . . ? C27 C26 C25 119.9(3) . . ? C26 C27 C28 120.0(3) . . ? C27 C28 C23 121.4(3) . . ? C30 C29 C34 119.3(3) . . ? C30 C29 C12 120.8(3) . . ? C34 C29 C12 119.9(3) . . ? C31 C30 C29 120.4(3) . . ? C30 C31 C32 120.8(4) . . ? C33 C32 C31 119.1(4) . . ? C32 C33 C34 121.1(4) . . ? C33 C34 C29 119.3(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.202 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.043