# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_MH-188-01 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C21 H13 Br F N O8 S2' _chemical_formula_moiety 'C21 H13 Br F N O8 S2' _chemical_formula_weight 570.36 _chemical_melting_point ? _chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 8.3933(17) _cell_length_b 10.672(2) _cell_length_c 13.178(3) _cell_angle_alpha 90.0000 _cell_angle_beta 101.288(3) _cell_angle_gamma 90.0000 _cell_volume 1157.5(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3762 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 31.20 _cell_measurement_temperature 223 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.300 _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572.00 _exptl_absorpt_coefficient_mu 2.017 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'NUMABS (Rigaku, 1999)' _exptl_absorpt_correction_T_min 0.486 _exptl_absorpt_correction_T_max 0.546 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 223 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 9001 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4829 _reflns_number_gt 4319 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1147 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4829 _refine_ls_number_parameters 321 _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0010Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.025 _refine_diff_density_max 1.350 _refine_diff_density_min -1.410 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 2028 Friedel Pairs' _refine_ls_abs_structure_Flack -0.021(10) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Br Br -0.2901 2.4595 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Br1 Br 0.21103(9) 0.56459(10) -0.46964(3) 0.1112(3) Uani 1.0 2 d . . . S1 S 0.23541(10) 0.27532(9) 0.07513(6) 0.0357(2) Uani 1.0 2 d . . . S2 S 0.31448(11) 0.31734(9) 0.29845(6) 0.0370(2) Uani 1.0 2 d . . . F1 F 0.5232(2) 0.32217(19) 0.17854(16) 0.0423(6) Uani 1.0 2 d . . . O1 O 0.3225(4) 0.2402(3) -0.0029(3) 0.0557(9) Uani 1.0 2 d . . . O2 O 0.0870(3) 0.3425(3) 0.04978(19) 0.0465(8) Uani 1.0 2 d . . . O3 O 0.4563(4) 0.3154(3) 0.3793(2) 0.0575(8) Uani 1.0 2 d . . . O4 O 0.1749(4) 0.3882(3) 0.3100(2) 0.0474(8) Uani 1.0 2 d . . . O5 O 0.3681(3) 0.5173(2) 0.05008(16) 0.0303(6) Uani 1.0 2 d . . . O6 O 0.2387(4) 0.7007(3) 0.0420(2) 0.0595(9) Uani 1.0 2 d . . . O7 O 0.9531(3) 0.5780(4) 0.1646(3) 0.0635(10) Uani 1.0 2 d . . . O8 O 1.0464(3) 0.6816(3) 0.3038(3) 0.0621(9) Uani 1.0 2 d . . . N1 N 0.9357(4) 0.6309(3) 0.2434(3) 0.0443(9) Uani 1.0 2 d . . . C1 C 0.3695(4) 0.3662(3) 0.1764(3) 0.0294(8) Uani 1.0 2 d . . . C2 C 0.3578(4) 0.5067(3) 0.1572(3) 0.0274(7) Uani 1.0 2 d . . . C3 C 0.4946(4) 0.5753(3) 0.2271(2) 0.0271(7) Uani 1.0 2 d . . . C4 C 0.6486(4) 0.5743(3) 0.2032(3) 0.0304(8) Uani 1.0 2 d . . . C5 C 0.7730(4) 0.6329(3) 0.2707(3) 0.0354(9) Uani 1.0 2 d . . . C6 C 0.7512(5) 0.6905(4) 0.3604(3) 0.0446(10) Uani 1.0 2 d . . . C7 C 0.5948(5) 0.6912(4) 0.3825(3) 0.0460(10) Uani 1.0 2 d . . . C8 C 0.4679(4) 0.6345(3) 0.3161(3) 0.0347(9) Uani 1.0 2 d . . . C9 C 0.2155(4) 0.1441(3) 0.1536(3) 0.0344(9) Uani 1.0 2 d . . . C10 C 0.2569(4) 0.1634(3) 0.2585(3) 0.0355(9) Uani 1.0 2 d . . . C11 C 0.2481(5) 0.0670(4) 0.3284(3) 0.0482(10) Uani 1.0 2 d . . . C12 C 0.1968(6) -0.0494(4) 0.2874(4) 0.0555(13) Uani 1.0 2 d . . . C13 C 0.1561(5) -0.0676(4) 0.1829(4) 0.0524(12) Uani 1.0 2 d . . . C14 C 0.1642(5) 0.0285(4) 0.1133(3) 0.0436(10) Uani 1.0 2 d . . . C15 C 0.2908(4) 0.6174(4) -0.0013(3) 0.0343(8) Uani 1.0 2 d . . . C16 C 0.2798(4) 0.6048(3) -0.1145(3) 0.0339(8) Uani 1.0 2 d . . . C17 C 0.1830(4) 0.6916(4) -0.1777(3) 0.0441(10) Uani 1.0 2 d . . . C18 C 0.1641(5) 0.6803(5) -0.2838(3) 0.0576(12) Uani 1.0 2 d . . . C19 C 0.2433(6) 0.5840(6) -0.3251(3) 0.0644(13) Uani 1.0 2 d . . . C20 C 0.3421(6) 0.5005(5) -0.2623(3) 0.0585(13) Uani 1.0 2 d . . . C21 C 0.3576(5) 0.5085(4) -0.1560(3) 0.0442(10) Uani 1.0 2 d . . . H2 H 0.2516 0.5385 0.1680 0.0337 Uiso 1.0 2 calc R . . H4 H 0.6677 0.5349 0.1429 0.0370 Uiso 1.0 2 calc R . . H6 H 0.8386 0.7286 0.4054 0.0516 Uiso 1.0 2 calc R . . H7 H 0.5762 0.7304 0.4429 0.0551 Uiso 1.0 2 calc R . . H8 H 0.3631 0.6357 0.3313 0.0426 Uiso 1.0 2 calc R . . H11 H 0.2758 0.0801 0.4002 0.0578 Uiso 1.0 2 calc R . . H12 H 0.1899 -0.1167 0.3324 0.0675 Uiso 1.0 2 calc R . . H13 H 0.1217 -0.1475 0.1576 0.0641 Uiso 1.0 2 calc R . . H14 H 0.1357 0.0153 0.0415 0.0535 Uiso 1.0 2 calc R . . H17 H 0.1315 0.7568 -0.1486 0.0532 Uiso 1.0 2 calc R . . H18 H 0.0983 0.7371 -0.3277 0.0682 Uiso 1.0 2 calc R . . H20 H 0.3980 0.4382 -0.2917 0.0723 Uiso 1.0 2 calc R . . H21 H 0.4208 0.4497 -0.1126 0.0535 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.1295(6) 0.1776(8) 0.0261(2) -0.0395(6) 0.0144(3) -0.0109(4) S1 0.0433(4) 0.0361(5) 0.0280(4) -0.0073(4) 0.0081(3) -0.0060(3) S2 0.0541(5) 0.0303(4) 0.0267(4) -0.0070(4) 0.0083(3) -0.0007(3) F1 0.0328(9) 0.0351(10) 0.0592(13) 0.0066(8) 0.0093(8) -0.0038(10) O1 0.0819(19) 0.0510(17) 0.0416(15) -0.0170(14) 0.0305(14) -0.0197(12) O2 0.0431(13) 0.0494(17) 0.0427(14) -0.0079(11) -0.0022(11) 0.0014(12) O3 0.0789(19) 0.0500(16) 0.0349(14) -0.0190(15) -0.0098(13) 0.0072(12) O4 0.0665(16) 0.0388(15) 0.0431(14) -0.0029(12) 0.0262(12) -0.0057(11) O5 0.0343(10) 0.0339(12) 0.0241(10) 0.0020(9) 0.0092(8) -0.0018(8) O6 0.088(2) 0.0571(19) 0.0369(14) 0.0373(16) 0.0210(14) 0.0083(12) O7 0.0390(14) 0.094(3) 0.0612(18) -0.0004(15) 0.0191(13) -0.0033(18) O8 0.0358(13) 0.0598(19) 0.085(3) -0.0153(13) -0.0034(14) 0.0121(16) N1 0.0331(14) 0.0455(18) 0.0522(19) -0.0085(13) 0.0037(13) 0.0165(14) C1 0.0301(14) 0.0309(16) 0.0279(14) 0.0004(12) 0.0077(11) -0.0026(12) C2 0.0280(13) 0.0306(16) 0.0255(14) 0.0014(11) 0.0097(11) 0.0004(11) C3 0.0319(14) 0.0259(15) 0.0239(12) -0.0007(12) 0.0061(11) 0.0003(11) C4 0.0314(14) 0.0321(17) 0.0290(14) -0.0009(12) 0.0089(11) 0.0001(13) C5 0.0330(15) 0.0333(17) 0.0395(18) -0.0021(13) 0.0062(13) 0.0073(14) C6 0.0454(19) 0.044(2) 0.0388(19) -0.0100(16) -0.0046(15) -0.0038(16) C7 0.058(2) 0.046(2) 0.0343(18) -0.0030(18) 0.0097(16) -0.0118(16) C8 0.0390(16) 0.0376(18) 0.0298(16) -0.0010(13) 0.0123(13) -0.0051(13) C9 0.0366(16) 0.0321(17) 0.0364(17) -0.0031(13) 0.0114(13) -0.0027(13) C10 0.0415(17) 0.0259(17) 0.0396(18) -0.0046(13) 0.0089(14) -0.0025(13) C11 0.069(3) 0.037(2) 0.0393(18) -0.0042(18) 0.0111(16) 0.0060(16) C12 0.073(3) 0.036(3) 0.060(3) -0.0063(19) 0.019(2) 0.0032(18) C13 0.063(3) 0.035(2) 0.062(3) -0.0074(17) 0.020(2) -0.0094(17) C14 0.054(2) 0.0339(19) 0.047(2) -0.0116(16) 0.0186(16) -0.0148(16) C15 0.0361(16) 0.0394(19) 0.0289(15) 0.0012(13) 0.0101(13) 0.0001(13) C16 0.0328(15) 0.0417(19) 0.0283(15) -0.0050(13) 0.0086(12) 0.0012(13) C17 0.0326(16) 0.062(3) 0.0386(18) -0.0036(16) 0.0093(14) 0.0161(17) C18 0.046(2) 0.089(4) 0.0353(19) -0.007(2) 0.0022(16) 0.016(2) C19 0.066(3) 0.102(4) 0.0265(17) -0.036(3) 0.0112(17) -0.010(3) C20 0.067(3) 0.075(3) 0.039(2) -0.017(3) 0.0231(19) -0.016(2) C21 0.0497(19) 0.052(3) 0.0316(17) -0.0049(17) 0.0108(15) -0.0054(15) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Br1 C19 1.882(4) yes . . S1 O1 1.424(4) yes . . S1 O2 1.419(3) yes . . S1 C1 1.844(3) yes . . S1 C9 1.768(4) yes . . S2 O3 1.434(3) yes . . S2 O4 1.427(3) yes . . S2 C1 1.834(4) yes . . S2 C10 1.763(4) yes . . F1 C1 1.368(4) yes . . O5 C2 1.435(4) yes . . O5 C15 1.360(4) yes . . O6 C15 1.185(5) yes . . O7 N1 1.215(5) yes . . O8 N1 1.225(4) yes . . N1 C5 1.479(5) yes . . C1 C2 1.520(5) yes . . C2 C3 1.513(4) yes . . C3 C4 1.389(5) yes . . C3 C8 1.389(5) yes . . C4 C5 1.381(5) yes . . C5 C6 1.376(6) yes . . C6 C7 1.398(6) yes . . C7 C8 1.379(5) yes . . C9 C10 1.374(5) yes . . C9 C14 1.378(5) yes . . C10 C11 1.393(6) yes . . C11 C12 1.389(6) yes . . C12 C13 1.366(7) yes . . C13 C14 1.386(6) yes . . C15 C16 1.482(5) yes . . C16 C17 1.396(5) yes . . C16 C21 1.386(6) yes . . C17 C18 1.381(6) yes . . C18 C19 1.392(8) yes . . C19 C20 1.377(7) yes . . C20 C21 1.384(6) yes . . C2 H2 0.990 no . . C4 H4 0.940 no . . C6 H6 0.940 no . . C7 H7 0.940 no . . C8 H8 0.940 no . . C11 H11 0.940 no . . C12 H12 0.940 no . . C13 H13 0.940 no . . C14 H14 0.940 no . . C17 H17 0.940 no . . C18 H18 0.940 no . . C20 H20 0.940 no . . C21 H21 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 S1 O2 120.93(16) yes . . . O1 S1 C1 109.54(16) yes . . . O1 S1 C9 109.54(18) yes . . . O2 S1 C1 106.73(15) yes . . . O2 S1 C9 111.03(17) yes . . . C1 S1 C9 96.18(15) yes . . . O3 S2 O4 120.50(17) yes . . . O3 S2 C1 109.94(16) yes . . . O3 S2 C10 110.32(17) yes . . . O4 S2 C1 107.21(15) yes . . . O4 S2 C10 110.06(16) yes . . . C1 S2 C10 95.99(16) yes . . . C2 O5 C15 115.9(3) yes . . . O7 N1 O8 123.8(4) yes . . . O7 N1 C5 119.1(3) yes . . . O8 N1 C5 117.0(4) yes . . . S1 C1 S2 105.19(16) yes . . . S1 C1 F1 105.9(2) yes . . . S1 C1 C2 112.82(19) yes . . . S2 C1 F1 106.4(2) yes . . . S2 C1 C2 114.0(3) yes . . . F1 C1 C2 111.9(3) yes . . . O5 C2 C1 103.1(3) yes . . . O5 C2 C3 112.1(3) yes . . . C1 C2 C3 111.1(3) yes . . . C2 C3 C4 119.2(3) yes . . . C2 C3 C8 120.4(3) yes . . . C4 C3 C8 120.4(3) yes . . . C3 C4 C5 118.0(3) yes . . . N1 C5 C4 117.0(3) yes . . . N1 C5 C6 120.0(3) yes . . . C4 C5 C6 123.0(4) yes . . . C5 C6 C7 118.0(3) yes . . . C6 C7 C8 120.4(4) yes . . . C3 C8 C7 120.2(4) yes . . . S1 C9 C10 115.8(3) yes . . . S1 C9 C14 122.8(3) yes . . . C10 C9 C14 121.4(4) yes . . . S2 C10 C9 116.2(3) yes . . . S2 C10 C11 122.5(3) yes . . . C9 C10 C11 121.3(3) yes . . . C10 C11 C12 117.1(4) yes . . . C11 C12 C13 121.1(4) yes . . . C12 C13 C14 121.8(4) yes . . . C9 C14 C13 117.3(4) yes . . . O5 C15 O6 122.3(3) yes . . . O5 C15 C16 111.0(3) yes . . . O6 C15 C16 126.6(3) yes . . . C15 C16 C17 117.1(3) yes . . . C15 C16 C21 121.6(3) yes . . . C17 C16 C21 121.3(4) yes . . . C16 C17 C18 119.0(4) yes . . . C17 C18 C19 119.5(4) yes . . . Br1 C19 C18 119.5(4) yes . . . Br1 C19 C20 119.2(4) yes . . . C18 C19 C20 121.3(4) yes . . . C19 C20 C21 119.7(5) yes . . . C16 C21 C20 119.2(4) yes . . . O5 C2 H2 110.101 no . . . C1 C2 H2 110.178 no . . . C3 C2 H2 110.105 no . . . C3 C4 H4 120.973 no . . . C5 C4 H4 120.981 no . . . C5 C6 H6 121.045 no . . . C7 C6 H6 120.996 no . . . C6 C7 H7 119.780 no . . . C8 C7 H7 119.809 no . . . C3 C8 H8 119.943 no . . . C7 C8 H8 119.865 no . . . C10 C11 H11 121.430 no . . . C12 C11 H11 121.469 no . . . C11 C12 H12 119.327 no . . . C13 C12 H12 119.569 no . . . C12 C13 H13 119.001 no . . . C14 C13 H13 119.199 no . . . C9 C14 H14 121.372 no . . . C13 C14 H14 121.284 no . . . C16 C17 H17 120.542 no . . . C18 C17 H17 120.460 no . . . C17 C18 H18 120.290 no . . . C19 C18 H18 120.254 no . . . C19 C20 H20 120.046 no . . . C21 C20 H20 120.303 no . . . C16 C21 H21 120.521 no . . . C20 C21 H21 120.312 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O1 S1 C1 S2 -142.76(17) no . . . . O1 S1 C1 F1 -30.3(3) no . . . . O1 S1 C1 C2 92.3(3) no . . . . O1 S1 C9 C10 131.0(3) no . . . . O1 S1 C9 C14 -48.1(3) no . . . . O2 S1 C1 S2 84.70(18) no . . . . O2 S1 C1 F1 -162.88(19) no . . . . O2 S1 C1 C2 -40.2(3) no . . . . O2 S1 C9 C10 -92.9(3) no . . . . O2 S1 C9 C14 88.0(3) no . . . . C1 S1 C9 C10 17.7(3) no . . . . C1 S1 C9 C14 -161.4(3) no . . . . C9 S1 C1 S2 -29.47(18) no . . . . C9 S1 C1 F1 82.9(2) no . . . . C9 S1 C1 C2 -154.4(2) no . . . . O3 S2 C1 S1 144.76(17) no . . . . O3 S2 C1 F1 32.7(3) no . . . . O3 S2 C1 C2 -91.1(2) no . . . . O3 S2 C10 C9 -135.7(3) no . . . . O3 S2 C10 C11 46.4(3) no . . . . O4 S2 C1 S1 -82.59(18) no . . . . O4 S2 C1 F1 165.35(18) no . . . . O4 S2 C1 C2 41.5(2) no . . . . O4 S2 C10 C9 88.9(3) no . . . . O4 S2 C10 C11 -88.9(3) no . . . . C1 S2 C10 C9 -21.8(3) no . . . . C1 S2 C10 C11 160.3(3) no . . . . C10 S2 C1 S1 30.59(17) no . . . . C10 S2 C1 F1 -81.5(2) no . . . . C10 S2 C1 C2 154.73(18) no . . . . C2 O5 C15 O6 10.8(4) no . . . . C2 O5 C15 C16 -168.1(2) no . . . . C15 O5 C2 C1 151.2(2) no . . . . C15 O5 C2 C3 -89.3(3) no . . . . O7 N1 C5 C4 -0.5(5) no . . . . O7 N1 C5 C6 178.9(3) no . . . . O8 N1 C5 C4 -179.2(3) no . . . . O8 N1 C5 C6 0.3(5) no . . . . S1 C1 C2 O5 -47.0(3) no . . . . S1 C1 C2 C3 -167.21(18) no . . . . S2 C1 C2 O5 -166.93(16) no . . . . S2 C1 C2 C3 72.9(3) no . . . . F1 C1 C2 O5 72.3(3) no . . . . F1 C1 C2 C3 -47.9(4) no . . . . O5 C2 C3 C4 -37.4(4) no . . . . O5 C2 C3 C8 145.1(3) no . . . . C1 C2 C3 C4 77.4(4) no . . . . C1 C2 C3 C8 -100.1(3) no . . . . C2 C3 C4 C5 -177.2(3) no . . . . C2 C3 C8 C7 176.5(3) no . . . . C4 C3 C8 C7 -0.9(5) no . . . . C8 C3 C4 C5 0.3(5) no . . . . C3 C4 C5 N1 -179.8(3) no . . . . C3 C4 C5 C6 0.8(5) no . . . . N1 C5 C6 C7 179.3(3) no . . . . C4 C5 C6 C7 -1.3(5) no . . . . C5 C6 C7 C8 0.6(6) no . . . . C6 C7 C8 C3 0.5(5) no . . . . S1 C9 C10 S2 2.8(4) no . . . . S1 C9 C10 C11 -179.3(2) no . . . . S1 C9 C14 C13 179.0(3) no . . . . C10 C9 C14 C13 -0.0(5) no . . . . C14 C9 C10 S2 -178.2(3) no . . . . C14 C9 C10 C11 -0.2(5) no . . . . S2 C10 C11 C12 178.2(3) no . . . . C9 C10 C11 C12 0.5(6) no . . . . C10 C11 C12 C13 -0.4(7) no . . . . C11 C12 C13 C14 0.1(7) no . . . . C12 C13 C14 C9 0.1(6) no . . . . O5 C15 C16 C17 171.0(3) no . . . . O5 C15 C16 C21 -6.9(4) no . . . . O6 C15 C16 C17 -7.8(5) no . . . . O6 C15 C16 C21 174.3(4) no . . . . C15 C16 C17 C18 -177.5(3) no . . . . C15 C16 C21 C20 179.4(3) no . . . . C17 C16 C21 C20 1.6(6) no . . . . C21 C16 C17 C18 0.4(5) no . . . . C16 C17 C18 C19 -0.8(6) no . . . . C17 C18 C19 Br1 177.6(4) no . . . . C17 C18 C19 C20 -0.9(7) no . . . . Br1 C19 C20 C21 -175.5(3) no . . . . C18 C19 C20 C21 3.0(7) no . . . . C19 C20 C21 C16 -3.3(7) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S1 O4 3.450(3) no . . S1 O5 2.857(3) no . . S2 O2 3.465(3) no . . S2 C3 3.363(4) no . . F1 O1 2.783(4) no . . F1 O3 2.811(4) no . . F1 O5 2.834(3) no . . F1 C3 2.797(4) no . . F1 C4 2.884(4) no . . F1 C9 3.171(4) no . . F1 C10 3.146(4) no . . O1 O5 3.046(4) no . . O1 C2 3.519(5) no . . O1 C14 3.164(5) no . . O1 C21 3.548(5) no . . O2 O4 3.399(4) no . . O2 O5 3.007(4) no . . O2 C2 2.997(4) no . . O2 C10 3.423(4) no . . O2 C14 3.483(5) no . . O2 C15 3.527(5) no . . O3 C2 3.532(4) no . . O3 C3 3.476(4) no . . O3 C8 3.512(5) no . . O3 C11 3.174(5) no . . O4 C2 3.037(5) no . . O4 C8 3.589(5) no . . O4 C9 3.380(5) no . . O4 C11 3.482(5) no . . O5 C4 2.850(4) no . . O5 C21 2.702(5) no . . O6 C2 2.645(4) no . . O6 C3 3.209(4) no . . O6 C17 2.843(5) no . . O7 C4 2.702(5) no . . O7 C6 3.561(6) no . . O8 C4 3.533(4) no . . O8 C6 2.726(5) no . . C1 C4 3.197(5) no . . C1 C8 3.417(5) no . . C1 C15 3.535(5) no . . C3 C6 2.785(5) no . . C3 C15 3.189(4) no . . C4 C7 2.785(5) no . . C5 C8 2.742(5) no . . C9 C12 2.740(6) no . . C10 C13 2.730(5) no . . C11 C14 2.814(6) no . . C16 C19 2.742(5) no . . C17 C20 2.787(7) no . . C18 C21 2.786(6) no . . Br1 O4 3.424(3) no . 1_554 Br1 O8 3.282(4) no . 1_454 F1 C16 3.062(4) no . 2_645 F1 C17 2.835(4) no . 2_645 F1 C18 3.112(5) no . 2_645 F1 C19 3.543(6) no . 2_645 F1 C21 3.523(5) no . 2_645 O1 O7 3.310(4) no . 2_645 O1 C4 3.227(5) no . 2_645 O1 C15 3.491(5) no . 2_645 O2 O6 3.151(4) no . 2_545 O2 O7 3.246(5) no . 1_455 O2 C13 3.469(5) no . 2_555 O2 C14 3.351(5) no . 2_555 O2 C17 3.474(5) no . 2_545 O3 C7 3.510(5) no . 2_646 O4 Br1 3.424(3) no . 1_556 O4 O7 3.138(4) no . 1_455 O4 O8 3.307(5) no . 1_455 O4 N1 3.290(4) no . 1_455 O4 C18 3.571(6) no . 2_545 O6 O2 3.151(4) no . 2_555 O6 O7 3.404(5) no . 1_455 O6 C13 3.248(6) no . 1_565 O7 O1 3.310(4) no . 2_655 O7 O2 3.246(5) no . 1_655 O7 O4 3.138(4) no . 1_655 O7 O6 3.404(5) no . 1_655 O7 C2 3.501(4) no . 1_655 O8 Br1 3.282(4) no . 1_656 O8 O4 3.307(5) no . 1_655 O8 C8 3.545(5) no . 1_655 O8 C12 3.160(6) no . 1_665 O8 C13 3.336(6) no . 1_665 N1 O4 3.290(4) no . 1_655 C2 O7 3.501(4) no . 1_455 C4 O1 3.227(5) no . 2_655 C6 C20 3.582(7) no . 2_655 C7 O3 3.510(5) no . 2_656 C8 O8 3.545(5) no . 1_455 C9 C17 3.458(5) no . 2_545 C12 O8 3.160(6) no . 1_445 C13 O2 3.469(5) no . 2_545 C13 O6 3.248(6) no . 1_545 C13 O8 3.336(6) no . 1_445 C14 O2 3.351(5) no . 2_545 C15 O1 3.491(5) no . 2_655 C16 F1 3.062(4) no . 2_655 C17 F1 2.835(4) no . 2_655 C17 O2 3.474(5) no . 2_555 C17 C9 3.458(5) no . 2_555 C18 F1 3.112(5) no . 2_655 C18 O4 3.571(6) no . 2_555 C19 F1 3.543(6) no . 2_655 C20 C6 3.582(7) no . 2_645 C21 F1 3.523(5) no . 2_655 Br1 H18 2.9116 no . . Br1 H20 2.8882 no . . S1 H2 3.0558 no . . S1 H14 2.9069 no . . S2 H2 2.9069 no . . S2 H8 3.4395 no . . S2 H11 2.9128 no . . F1 H2 3.2280 no . . F1 H4 2.6583 no . . O1 H14 2.9860 no . . O1 H21 2.8702 no . . O2 H2 2.8047 no . . O2 H14 3.5195 no . . O3 H8 3.5366 no . . O3 H11 2.9730 no . . O4 H2 2.6385 no . . O4 H8 3.0621 no . . O4 H11 3.5419 no . . O5 H4 2.5785 no . . O5 H21 2.3844 no . . O6 H2 2.3861 no . . O6 H17 2.5676 no . . O7 H4 2.4013 no . . O8 H6 2.4500 no . . N1 H4 2.5877 no . . N1 H6 2.6439 no . . C1 H4 3.1824 no . . C1 H8 3.5338 no . . C2 H4 2.6611 no . . C2 H8 2.6696 no . . C3 H7 3.2460 no . . C4 H2 3.2958 no . . C4 H6 3.2690 no . . C4 H8 3.2574 no . . C5 H7 3.2296 no . . C6 H4 3.2679 no . . C6 H8 3.2575 no . . C8 H2 2.6019 no . . C8 H4 3.2635 no . . C8 H6 3.2614 no . . C9 H11 3.2627 no . . C9 H13 3.2125 no . . C10 H12 3.2268 no . . C10 H14 3.2513 no . . C11 H13 3.2398 no . . C12 H14 3.2538 no . . C13 H11 3.2516 no . . C14 H12 3.2462 no . . C15 H2 2.4658 no . . C15 H4 3.4701 no . . C15 H17 2.5988 no . . C15 H21 2.6788 no . . C16 H18 3.2466 no . . C16 H20 3.2416 no . . C17 H21 3.2734 no . . C18 H20 3.2590 no . . C19 H17 3.2478 no . . C19 H21 3.2377 no . . C20 H18 3.2585 no . . C21 H17 3.2722 no . . H2 H4 3.5720 no . . H2 H8 2.4080 no . . H6 H7 2.3494 no . . H7 H8 2.3139 no . . H11 H12 2.3405 no . . H12 H13 2.2857 no . . H13 H14 2.3328 no . . H17 H18 2.3314 no . . H20 H21 2.3330 no . . Br1 H8 3.2241 no . 1_554 S1 H17 3.4101 no . 2_545 S2 H7 3.4778 no . 2_646 F1 H17 3.0807 no . 2_645 F1 H18 3.5128 no . 2_645 O1 H4 2.8758 no . 2_645 O2 H13 2.9449 no . 2_555 O2 H14 2.7317 no . 2_555 O2 H17 2.6137 no . 2_545 O3 H7 2.5756 no . 2_646 O4 H17 3.3111 no . 2_545 O4 H18 2.8497 no . 2_545 O6 H13 2.5490 no . 1_565 O6 H14 3.4668 no . 1_565 O7 H2 2.5320 no . 1_655 O7 H13 3.2621 no . 1_665 O7 H14 2.7548 no . 2_655 O7 H17 3.4985 no . 2_645 O8 H2 3.1153 no . 1_655 O8 H8 2.6566 no . 1_655 O8 H12 2.4597 no . 1_665 O8 H13 2.8133 no . 1_665 N1 H2 3.1656 no . 1_655 N1 H8 3.5479 no . 1_655 N1 H12 3.4936 no . 1_665 N1 H13 3.1624 no . 1_665 C5 H20 3.5922 no . 2_655 C6 H11 3.4154 no . 2_656 C6 H20 2.9883 no . 2_655 C7 H11 3.0928 no . 2_656 C7 H20 2.9002 no . 2_655 C8 H12 3.5691 no . 1_565 C8 H20 3.4662 no . 2_655 C9 H17 3.1403 no . 2_545 C10 H17 3.4457 no . 2_545 C10 H18 3.3771 no . 2_545 C11 H7 3.5437 no . 2_646 C11 H18 3.4261 no . 2_545 C11 H20 3.3927 no . 2_645 C12 H20 3.3929 no . 2_645 C14 H17 3.5728 no . 2_545 C14 H21 3.5851 no . 2_645 H2 O7 2.5320 no . 1_455 H2 O8 3.1153 no . 1_455 H2 N1 3.1656 no . 1_455 H2 H13 3.5186 no . 1_565 H4 O1 2.8758 no . 2_655 H4 H14 3.2004 no . 2_655 H4 H17 3.4058 no . 2_645 H6 H11 3.3096 no . 2_656 H6 H20 3.1663 no . 2_655 H7 S2 3.4778 no . 2_656 H7 O3 2.5756 no . 2_656 H7 C11 3.5437 no . 2_656 H7 H11 2.7171 no . 2_656 H7 H20 3.0169 no . 2_655 H8 Br1 3.2241 no . 1_556 H8 O8 2.6566 no . 1_455 H8 N1 3.5479 no . 1_455 H8 H12 3.0168 no . 1_565 H8 H13 3.5895 no . 1_565 H11 C6 3.4154 no . 2_646 H11 C7 3.0928 no . 2_646 H11 H6 3.3096 no . 2_646 H11 H7 2.7171 no . 2_646 H11 H18 3.5216 no . 2_545 H12 O8 2.4597 no . 1_445 H12 N1 3.4936 no . 1_445 H12 C8 3.5691 no . 1_545 H12 H8 3.0168 no . 1_545 H13 O2 2.9449 no . 2_545 H13 O6 2.5490 no . 1_545 H13 O7 3.2621 no . 1_445 H13 O8 2.8133 no . 1_445 H13 N1 3.1624 no . 1_445 H13 H2 3.5186 no . 1_545 H13 H8 3.5895 no . 1_545 H14 O2 2.7317 no . 2_545 H14 O6 3.4668 no . 1_545 H14 O7 2.7548 no . 2_645 H14 H4 3.2004 no . 2_645 H17 S1 3.4101 no . 2_555 H17 F1 3.0807 no . 2_655 H17 O2 2.6137 no . 2_555 H17 O4 3.3111 no . 2_555 H17 O7 3.4985 no . 2_655 H17 C9 3.1403 no . 2_555 H17 C10 3.4457 no . 2_555 H17 C14 3.5728 no . 2_555 H17 H4 3.4058 no . 2_655 H18 F1 3.5128 no . 2_655 H18 O4 2.8497 no . 2_555 H18 C10 3.3771 no . 2_555 H18 C11 3.4261 no . 2_555 H18 H11 3.5216 no . 2_555 H20 C5 3.5922 no . 2_645 H20 C6 2.9883 no . 2_645 H20 C7 2.9002 no . 2_645 H20 C8 3.4662 no . 2_645 H20 C11 3.3927 no . 2_655 H20 C12 3.3929 no . 2_655 H20 H6 3.1663 no . 2_645 H20 H7 3.0169 no . 2_645 H21 C14 3.5851 no . 2_655 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 956341'