# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email koert@chemie.uni-marburg.de _publ_contact_author_name 'Ulrich Koert' loop_ _publ_author_name 'Ulrich Koert' 'Niels Muenster' 'Klaus Harms' # Attachment 'web_deposit_cif_file_1_KlausHarms_1319448416.nm144.cif' data_nm144 _database_code_depnum_ccdc_archive 'CCDC 850197' #TrackingRef 'web_deposit_cif_file_1_KlausHarms_1319448416.nm144.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 Br1 N2 O9 S1' _chemical_formula_sum 'C20 H21 Br N2 O9 S' _chemical_formula_weight 545.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 14.8023(7) _cell_length_b 7.0370(3) _cell_length_c 22.5089(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.697(4) _cell_angle_gamma 90.00 _cell_volume 2267.90(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15514 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 1.959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5290 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16860 _diffrn_reflns_av_R_equivalents 0.0895 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.15 _reflns_number_total 3288 _reflns_number_gt 2306 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 3.2' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0426P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3288 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _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 C1 C 0.9750(2) 0.7359(6) 0.66516(15) 0.0334(9) Uani 1 1 d . . . H1 H 1.0211 0.6710 0.6994 0.040 Uiso 1 1 calc R . . C2 C 1.0222(2) 0.9108(6) 0.64755(15) 0.0327(9) Uani 1 1 d . . . H2A H 0.9782 0.9733 0.6125 0.039 Uiso 1 1 calc R . . H2B H 1.0345 1.0009 0.6825 0.039 Uiso 1 1 calc R . . C3 C 1.1131(2) 0.8745(6) 0.63019(14) 0.0288(8) Uani 1 1 d . . . H3 H 1.1022 0.7835 0.5950 0.035 Uiso 1 1 calc R . . C4 C 1.1600(2) 1.0540(6) 0.61436(14) 0.0322(9) Uani 1 1 d . . . H4 H 1.1656 1.1472 0.6487 0.039 Uiso 1 1 calc R . . C5 C 1.2573(2) 1.0134(6) 0.60664(16) 0.0380(9) Uani 1 1 d . . . H5A H 1.2531 0.9218 0.5732 0.057 Uiso 1 1 calc R . . H5B H 1.2962 0.9605 0.6449 0.057 Uiso 1 1 calc R . . H5C H 1.2853 1.1316 0.5968 0.057 Uiso 1 1 calc R . . C6 C 1.1011(3) 1.1447(6) 0.55517(16) 0.0394(10) Uani 1 1 d . . . H6A H 1.0942 1.0546 0.5211 0.059 Uiso 1 1 calc R . . H6B H 1.1322 1.2601 0.5460 0.059 Uiso 1 1 calc R . . H6C H 1.0393 1.1775 0.5605 0.059 Uiso 1 1 calc R . . C7 C 1.2185(2) 0.6251(6) 0.67743(15) 0.0316(9) Uani 1 1 d . . . C8 C 1.2929(2) 0.5749(6) 0.73438(14) 0.0282(8) Uani 1 1 d . . . C9 C 1.3350(2) 0.3998(6) 0.73618(14) 0.0310(9) Uani 1 1 d . . . H9 H 1.3131 0.3103 0.7042 0.037 Uiso 1 1 calc R . . C10 C 1.4102(2) 0.3556(6) 0.78559(15) 0.0302(8) Uani 1 1 d . . . C11 C 1.4439(2) 0.4838(5) 0.83272(14) 0.0297(8) Uani 1 1 d . . . H11 H 1.4954 0.4534 0.8661 0.036 Uiso 1 1 calc R . . C12 C 1.3998(2) 0.6563(6) 0.82913(14) 0.0292(8) Uani 1 1 d . . . C13 C 1.3230(2) 0.7053(6) 0.78140(14) 0.0305(8) Uani 1 1 d . . . H13 H 1.2923 0.8241 0.7811 0.037 Uiso 1 1 calc R . . C14 C 0.7963(2) 0.9085(5) 0.63132(14) 0.0288(8) Uani 1 1 d . . . C15 C 0.8076(2) 1.1005(5) 0.62144(15) 0.0315(8) Uani 1 1 d . . . H15 H 0.8563 1.1689 0.6487 0.038 Uiso 1 1 calc R . . C16 C 0.7485(2) 1.1944(6) 0.57208(15) 0.0337(9) Uani 1 1 d . . . H16 H 0.7574 1.3250 0.5645 0.040 Uiso 1 1 calc R . . C17 C 0.6752(2) 1.0904(6) 0.53372(15) 0.0332(9) Uani 1 1 d . . . C18 C 0.6629(2) 0.8990(6) 0.54446(15) 0.0320(9) Uani 1 1 d . . . H18 H 0.6125 0.8313 0.5185 0.038 Uiso 1 1 calc R . . C19 C 0.7236(2) 0.8062(6) 0.59275(14) 0.0320(9) Uani 1 1 d . . . H19 H 0.7159 0.6746 0.5996 0.038 Uiso 1 1 calc R . . C20 C 0.6208(3) 1.3672(6) 0.47236(17) 0.0492(11) Uani 1 1 d . . . H20A H 0.6812 1.3907 0.4633 0.074 Uiso 1 1 calc R . . H20B H 0.6167 1.4418 0.5083 0.074 Uiso 1 1 calc R . . H20C H 0.5704 1.4045 0.4370 0.074 Uiso 1 1 calc R . . N1 N 1.4575(2) 0.1733(5) 0.78606(13) 0.0335(7) Uani 1 1 d . . . N2 N 1.4367(2) 0.7956(5) 0.87781(12) 0.0340(8) Uani 1 1 d . . . O1 O 1.17581(15) 0.7880(4) 0.68473(9) 0.0294(6) Uani 1 1 d . . . O2 O 1.20426(17) 0.5306(4) 0.63101(10) 0.0378(7) Uani 1 1 d . . . O3 O 1.42037(17) 0.0516(4) 0.74837(10) 0.0373(6) Uani 1 1 d . . . O4 O 1.53256(17) 0.1508(4) 0.82437(11) 0.0396(7) Uani 1 1 d . . . O5 O 1.50868(18) 0.7544(4) 0.91649(11) 0.0464(8) Uani 1 1 d . . . O6 O 1.39466(17) 0.9471(4) 0.87702(10) 0.0337(6) Uani 1 1 d . . . O7 O 0.83187(17) 0.6167(4) 0.70506(10) 0.0376(6) Uani 1 1 d . . . O8 O 0.90693(16) 0.9254(4) 0.74193(10) 0.0360(6) Uani 1 1 d . . . O9 O 0.61242(18) 1.1678(4) 0.48488(10) 0.0393(7) Uani 1 1 d . . . S1 S 0.87358(6) 0.79163(15) 0.69239(4) 0.0311(2) Uani 1 1 d . . . Br1 Br 0.94050(3) 0.55731(6) 0.597138(16) 0.03774(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.030(2) 0.040(2) 0.0283(17) 0.0047(16) 0.0041(14) -0.0009(18) C2 0.0277(19) 0.041(3) 0.0269(17) -0.0013(16) 0.0032(13) 0.0016(17) C3 0.0260(19) 0.034(2) 0.0229(16) -0.0015(15) 0.0001(13) -0.0007(16) C4 0.034(2) 0.037(2) 0.0242(16) -0.0019(16) 0.0048(14) -0.0016(18) C5 0.033(2) 0.046(3) 0.0346(19) 0.0039(18) 0.0090(15) -0.0042(19) C6 0.037(2) 0.044(3) 0.0327(19) 0.0036(18) 0.0023(16) 0.001(2) C7 0.0219(18) 0.040(2) 0.0317(19) 0.0037(17) 0.0044(14) 0.0010(18) C8 0.0247(18) 0.036(2) 0.0246(16) -0.0006(16) 0.0072(13) 0.0010(17) C9 0.0242(18) 0.043(3) 0.0261(17) -0.0030(16) 0.0072(13) -0.0026(17) C10 0.0252(18) 0.037(2) 0.0304(18) 0.0037(16) 0.0097(14) 0.0043(17) C11 0.0238(17) 0.037(2) 0.0274(17) 0.0006(15) 0.0048(13) -0.0037(17) C12 0.0269(18) 0.036(2) 0.0233(17) -0.0032(15) 0.0040(13) -0.0022(17) C13 0.0228(18) 0.039(2) 0.0310(18) 0.0040(16) 0.0083(14) -0.0002(17) C14 0.0259(18) 0.033(2) 0.0268(16) 0.0016(15) 0.0058(13) -0.0007(16) C15 0.0273(19) 0.034(2) 0.0333(18) -0.0051(16) 0.0078(14) -0.0009(17) C16 0.032(2) 0.037(2) 0.0339(19) 0.0028(17) 0.0103(15) 0.0022(18) C17 0.0292(19) 0.040(2) 0.0285(17) 0.0013(17) 0.0043(14) 0.0069(18) C18 0.0290(19) 0.037(2) 0.0279(17) -0.0018(16) 0.0032(14) 0.0001(17) C19 0.033(2) 0.034(2) 0.0276(17) -0.0030(16) 0.0053(14) 0.0000(18) C20 0.064(3) 0.045(3) 0.033(2) 0.0079(19) 0.0019(18) 0.013(2) N1 0.0301(17) 0.042(2) 0.0303(15) 0.0026(15) 0.0106(13) 0.0035(15) N2 0.0317(17) 0.040(2) 0.0286(16) 0.0004(14) 0.0041(13) -0.0035(16) O1 0.0256(13) 0.0357(16) 0.0243(12) 0.0010(10) 0.0013(9) 0.0045(12) O2 0.0381(14) 0.0394(17) 0.0311(13) -0.0071(12) 0.0000(11) 0.0036(13) O3 0.0390(14) 0.0398(17) 0.0339(13) -0.0058(12) 0.0106(11) 0.0013(13) O4 0.0288(14) 0.0513(19) 0.0367(14) 0.0024(13) 0.0046(11) 0.0071(13) O5 0.0413(16) 0.0440(18) 0.0400(15) 0.0003(13) -0.0155(12) 0.0017(14) O6 0.0322(13) 0.0380(16) 0.0307(12) -0.0017(12) 0.0079(10) 0.0025(13) O7 0.0335(14) 0.0453(18) 0.0323(13) 0.0097(12) 0.0053(10) -0.0047(13) O8 0.0317(13) 0.0494(18) 0.0243(11) -0.0069(12) 0.0021(10) -0.0018(13) O9 0.0424(15) 0.0423(18) 0.0285(13) 0.0051(12) 0.0005(11) 0.0103(14) S1 0.0270(5) 0.0398(6) 0.0244(4) 0.0016(4) 0.0027(3) -0.0006(4) Br1 0.0333(2) 0.0406(3) 0.0381(2) -0.00701(18) 0.00685(14) -0.00433(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.516(5) . ? C1 S1 1.802(4) . ? C1 Br1 1.946(4) . ? C1 H1 1.0000 . ? C2 C3 1.515(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O1 1.470(4) . ? C3 C4 1.526(5) . ? C3 H3 1.0000 . ? C4 C5 1.522(5) . ? C4 C6 1.534(5) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 O2 1.211(4) . ? C7 O1 1.339(5) . ? C7 C8 1.505(4) . ? C8 C9 1.377(5) . ? C8 C13 1.386(5) . ? C9 C10 1.395(5) . ? C9 H9 0.9500 . ? C10 C11 1.385(5) . ? C10 N1 1.460(5) . ? C11 C12 1.371(5) . ? C11 H11 0.9500 . ? C12 C13 1.395(4) . ? C12 N2 1.468(5) . ? C13 H13 0.9500 . ? C14 C15 1.386(5) . ? C14 C19 1.399(5) . ? C14 S1 1.754(3) . ? C15 C16 1.394(5) . ? C15 H15 0.9500 . ? C16 C17 1.408(5) . ? C16 H16 0.9500 . ? C17 O9 1.360(4) . ? C17 C18 1.389(5) . ? C18 C19 1.385(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O9 1.443(5) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N1 O4 1.232(3) . ? N1 O3 1.232(4) . ? N2 O5 1.227(4) . ? N2 O6 1.232(4) . ? O7 S1 1.438(3) . ? O8 S1 1.447(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 S1 113.0(3) . . ? C2 C1 Br1 111.4(2) . . ? S1 C1 Br1 109.46(18) . . ? C2 C1 H1 107.6 . . ? S1 C1 H1 107.6 . . ? Br1 C1 H1 107.6 . . ? C3 C2 C1 115.4(3) . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? O1 C3 C2 105.6(3) . . ? O1 C3 C4 108.0(2) . . ? C2 C3 C4 114.0(3) . . ? O1 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? C5 C4 C3 111.8(3) . . ? C5 C4 C6 108.9(3) . . ? C3 C4 C6 110.8(3) . . ? C5 C4 H4 108.4 . . ? C3 C4 H4 108.4 . . ? C6 C4 H4 108.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C7 O1 126.3(3) . . ? O2 C7 C8 122.4(4) . . ? O1 C7 C8 111.2(3) . . ? C9 C8 C13 121.0(3) . . ? C9 C8 C7 117.6(3) . . ? C13 C8 C7 121.3(4) . . ? C8 C9 C10 119.1(3) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 121.7(4) . . ? C11 C10 N1 119.2(3) . . ? C9 C10 N1 119.1(3) . . ? C12 C11 C10 117.2(3) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? C11 C12 C13 123.2(3) . . ? C11 C12 N2 117.7(3) . . ? C13 C12 N2 119.1(3) . . ? C8 C13 C12 117.7(4) . . ? C8 C13 H13 121.1 . . ? C12 C13 H13 121.1 . . ? C15 C14 C19 120.5(3) . . ? C15 C14 S1 120.1(3) . . ? C19 C14 S1 119.4(3) . . ? C14 C15 C16 120.8(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C17 118.2(4) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? O9 C17 C18 115.8(3) . . ? O9 C17 C16 123.4(4) . . ? C18 C17 C16 120.8(3) . . ? C19 C18 C17 120.4(3) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C14 119.2(4) . . ? C18 C19 H19 120.4 . . ? C14 C19 H19 120.4 . . ? O9 C20 H20A 109.5 . . ? O9 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O9 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O4 N1 O3 123.9(3) . . ? O4 N1 C10 117.6(3) . . ? O3 N1 C10 118.5(3) . . ? O5 N2 O6 124.0(3) . . ? O5 N2 C12 117.6(3) . . ? O6 N2 C12 118.4(3) . . ? C7 O1 C3 118.0(3) . . ? C17 O9 C20 118.2(3) . . ? O7 S1 O8 118.93(15) . . ? O7 S1 C14 109.23(16) . . ? O8 S1 C14 109.03(17) . . ? O7 S1 C1 108.53(18) . . ? O8 S1 C1 104.65(16) . . ? C14 S1 C1 105.62(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C1 C2 C3 174.3(2) . . . . ? Br1 C1 C2 C3 -62.0(3) . . . . ? C1 C2 C3 O1 -60.1(4) . . . . ? C1 C2 C3 C4 -178.5(3) . . . . ? O1 C3 C4 C5 54.5(4) . . . . ? C2 C3 C4 C5 171.5(3) . . . . ? O1 C3 C4 C6 176.2(3) . . . . ? C2 C3 C4 C6 -66.8(4) . . . . ? O2 C7 C8 C9 -10.6(6) . . . . ? O1 C7 C8 C9 172.4(3) . . . . ? O2 C7 C8 C13 164.7(4) . . . . ? O1 C7 C8 C13 -12.3(5) . . . . ? C13 C8 C9 C10 -1.4(5) . . . . ? C7 C8 C9 C10 174.0(3) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C8 C9 C10 N1 -177.2(3) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? N1 C10 C11 C12 177.4(3) . . . . ? C10 C11 C12 C13 1.1(5) . . . . ? C10 C11 C12 N2 -178.1(3) . . . . ? C9 C8 C13 C12 2.7(5) . . . . ? C7 C8 C13 C12 -172.4(3) . . . . ? C11 C12 C13 C8 -2.6(6) . . . . ? N2 C12 C13 C8 176.5(3) . . . . ? C19 C14 C15 C16 -1.7(6) . . . . ? S1 C14 C15 C16 178.1(3) . . . . ? C14 C15 C16 C17 2.0(6) . . . . ? C15 C16 C17 O9 178.9(3) . . . . ? C15 C16 C17 C18 -0.7(6) . . . . ? O9 C17 C18 C19 179.4(3) . . . . ? C16 C17 C18 C19 -1.0(6) . . . . ? C17 C18 C19 C14 1.3(6) . . . . ? C15 C14 C19 C18 0.0(6) . . . . ? S1 C14 C19 C18 -179.8(3) . . . . ? C11 C10 N1 O4 -9.0(5) . . . . ? C9 C10 N1 O4 168.0(3) . . . . ? C11 C10 N1 O3 171.1(3) . . . . ? C9 C10 N1 O3 -11.9(5) . . . . ? C11 C12 N2 O5 4.9(5) . . . . ? C13 C12 N2 O5 -174.3(3) . . . . ? C11 C12 N2 O6 -176.1(3) . . . . ? C13 C12 N2 O6 4.7(5) . . . . ? O2 C7 O1 C3 -7.3(5) . . . . ? C8 C7 O1 C3 169.4(3) . . . . ? C2 C3 O1 C7 128.3(3) . . . . ? C4 C3 O1 C7 -109.3(3) . . . . ? C18 C17 O9 C20 178.8(3) . . . . ? C16 C17 O9 C20 -0.8(6) . . . . ? C15 C14 S1 O7 161.9(3) . . . . ? C19 C14 S1 O7 -18.3(3) . . . . ? C15 C14 S1 O8 30.5(3) . . . . ? C19 C14 S1 O8 -149.8(3) . . . . ? C15 C14 S1 C1 -81.5(3) . . . . ? C19 C14 S1 C1 98.3(3) . . . . ? C2 C1 S1 O7 177.4(2) . . . . ? Br1 C1 S1 O7 52.6(2) . . . . ? C2 C1 S1 O8 -54.7(3) . . . . ? Br1 C1 S1 O8 -179.44(17) . . . . ? C2 C1 S1 C14 60.4(3) . . . . ? Br1 C1 S1 C14 -64.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.807 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.807 _refine_diff_density_max 0.473 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.065 # Attachment 'web_deposit_cif_file_2_KlausHarms_1319448416.nm147.cif' data_nm147 _database_code_depnum_ccdc_archive 'CCDC 850198' #TrackingRef 'web_deposit_cif_file_2_KlausHarms_1319448416.nm147.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H31 Br N2 O9 S' _chemical_formula_sum 'C28 H31 Br N2 O9 S' _chemical_formula_weight 651.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4715(6) _cell_length_b 14.8297(7) _cell_length_c 19.0746(11) _cell_angle_alpha 87.467(4) _cell_angle_beta 89.464(5) _cell_angle_gamma 87.999(4) _cell_volume 2957.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9238 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 1.516 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7406 _exptl_absorpt_correction_T_max 0.8526 _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29197 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.1643 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.12 _reflns_number_total 10519 _reflns_number_gt 4455 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-AREA' _computing_structure_solution 'SIR2008 (Giacovazzo et al, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 3.2g' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0110P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10519 _refine_ls_number_parameters 749 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0524 _refine_ls_goodness_of_fit_ref 0.610 _refine_ls_restrained_S_all 0.610 _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 C1 C 0.8987(5) -0.0146(3) 0.1420(3) 0.0281(12) Uani 1 1 d . . . H1 H 0.8575 -0.0029 0.0952 0.034 Uiso 1 1 calc R . . C2 C 0.8985(4) -0.1157(3) 0.1592(3) 0.0249(12) Uani 1 1 d . . . H2A H 0.9294 -0.1276 0.2077 0.030 Uiso 1 1 calc R . . H2B H 0.9589 -0.1466 0.1272 0.030 Uiso 1 1 calc R . . C3 C 0.7669(5) -0.1559(3) 0.1528(2) 0.0269(12) Uani 1 1 d . . . H3 H 0.7004 -0.1132 0.1717 0.032 Uiso 1 1 calc R . . C4 C 0.7522(5) -0.2502(3) 0.1888(3) 0.0252(12) Uani 1 1 d . . . C5 C 0.6181(5) -0.2830(3) 0.1721(3) 0.0319(12) Uani 1 1 d . . . H5A H 0.6125 -0.2931 0.1218 0.048 Uiso 1 1 calc R . . H5B H 0.5534 -0.2371 0.1850 0.048 Uiso 1 1 calc R . . H5C H 0.6031 -0.3396 0.1989 0.048 Uiso 1 1 calc R . . C6 C 0.7602(6) -0.2390(3) 0.2695(3) 0.0386(14) Uani 1 1 d . . . H6A H 0.7450 -0.2970 0.2942 0.058 Uiso 1 1 calc R . . H6B H 0.6953 -0.1940 0.2838 0.058 Uiso 1 1 calc R . . H6C H 0.8452 -0.2188 0.2812 0.058 Uiso 1 1 calc R . . C7 C 0.8524(5) -0.3182(3) 0.1645(3) 0.0327(13) Uani 1 1 d . . . H7A H 0.8444 -0.3249 0.1138 0.049 Uiso 1 1 calc R . . H7B H 0.8401 -0.3766 0.1892 0.049 Uiso 1 1 calc R . . H7C H 0.9377 -0.2971 0.1746 0.049 Uiso 1 1 calc R . . C8 C 0.6789(5) -0.0996(3) 0.0418(3) 0.0244(13) Uani 1 1 d . . . C9 C 0.6487(5) -0.1263(3) -0.0309(3) 0.0237(12) Uani 1 1 d . . . C10 C 0.6163(4) -0.0568(3) -0.0794(3) 0.0234(12) Uani 1 1 d . . . H10 H 0.6096 0.0042 -0.0662 0.028 Uiso 1 1 calc R . . C11 C 0.5940(5) -0.0802(3) -0.1478(3) 0.0281(13) Uani 1 1 d . . . C12 C 0.5975(5) -0.1668(3) -0.1687(3) 0.0267(12) Uani 1 1 d . . . H12 H 0.5792 -0.1807 -0.2156 0.032 Uiso 1 1 calc R . . C13 C 0.6289(4) -0.2335(3) -0.1186(3) 0.0253(12) Uani 1 1 d . . . C14 C 0.6560(5) -0.2149(3) -0.0495(3) 0.0226(12) Uani 1 1 d . . . H14 H 0.6789 -0.2620 -0.0162 0.027 Uiso 1 1 calc R . . C15 C 1.0450(4) 0.1394(3) 0.1137(3) 0.0248(12) Uani 1 1 d . . . C16 C 1.0099(5) 0.1673(3) 0.0456(3) 0.0275(13) Uani 1 1 d . . . H16 H 0.9940 0.1242 0.0116 0.033 Uiso 1 1 calc R . . C17 C 0.9986(5) 0.2584(3) 0.0285(3) 0.0284(13) Uani 1 1 d . . . H17 H 0.9748 0.2779 -0.0178 0.034 Uiso 1 1 calc R . . C18 C 1.0211(5) 0.3218(3) 0.0774(3) 0.0250(12) Uani 1 1 d . . . C19 C 1.0563(5) 0.2939(3) 0.1461(3) 0.0284(13) Uani 1 1 d . . . H19 H 1.0731 0.3371 0.1799 0.034 Uiso 1 1 calc R . . C20 C 1.0660(5) 0.2029(3) 0.1635(3) 0.0266(13) Uani 1 1 d . . . H20 H 1.0873 0.1832 0.2101 0.032 Uiso 1 1 calc R . . C21 C 1.0349(6) 0.4782(3) 0.1022(3) 0.0407(15) Uani 1 1 d . . . H21A H 0.9767 0.4729 0.1426 0.061 Uiso 1 1 calc R . . H21B H 1.0224 0.5379 0.0787 0.061 Uiso 1 1 calc R . . H21C H 1.1234 0.4705 0.1182 0.061 Uiso 1 1 calc R . . C101 C 0.0967(5) 0.5276(3) 0.3533(2) 0.0245(12) Uani 1 1 d . . . H101 H 0.1397 0.5132 0.3993 0.029 Uiso 1 1 calc R . . C102 C 0.0971(5) 0.6301(3) 0.3396(3) 0.0272(12) Uani 1 1 d . . . H10A H 0.0661 0.6447 0.2914 0.033 Uiso 1 1 calc R . . H10B H 0.0364 0.6589 0.3726 0.033 Uiso 1 1 calc R . . C103 C 0.2283(5) 0.6701(3) 0.3476(2) 0.0227(12) Uani 1 1 d . . . H103 H 0.2944 0.6290 0.3266 0.027 Uiso 1 1 calc R . . C104 C 0.2445(5) 0.7665(3) 0.3162(3) 0.0277(12) Uani 1 1 d . . . C105 C 0.3768(5) 0.7980(3) 0.3350(3) 0.0298(12) Uani 1 1 d . . . H10C H 0.3910 0.8570 0.3115 0.045 Uiso 1 1 calc R . . H10D H 0.4421 0.7541 0.3195 0.045 Uiso 1 1 calc R . . H10E H 0.3822 0.8032 0.3859 0.045 Uiso 1 1 calc R . . C106 C 0.2378(5) 0.7616(3) 0.2354(2) 0.0330(13) Uani 1 1 d . . . H10F H 0.1522 0.7442 0.2222 0.050 Uiso 1 1 calc R . . H10G H 0.3013 0.7167 0.2196 0.050 Uiso 1 1 calc R . . H10H H 0.2556 0.8209 0.2135 0.050 Uiso 1 1 calc R . . C107 C 0.1420(5) 0.8322(3) 0.3424(3) 0.0321(13) Uani 1 1 d . . . H10I H 0.1480 0.8352 0.3935 0.048 Uiso 1 1 calc R . . H10J H 0.0575 0.8114 0.3303 0.048 Uiso 1 1 calc R . . H10K H 0.1543 0.8923 0.3204 0.048 Uiso 1 1 calc R . . C108 C 0.3192(5) 0.6045(3) 0.4545(3) 0.0240(13) Uani 1 1 d . . . C109 C 0.3482(5) 0.6219(3) 0.5285(3) 0.0246(13) Uani 1 1 d . . . C110 C 0.3439(5) 0.7069(3) 0.5555(3) 0.0267(13) Uani 1 1 d . . . H110 H 0.3213 0.7586 0.5264 0.032 Uiso 1 1 calc R . . C111 C 0.3732(5) 0.7159(3) 0.6260(3) 0.0270(12) Uani 1 1 d . . . C112 C 0.4067(5) 0.6418(3) 0.6696(3) 0.0290(13) Uani 1 1 d . . . H112 H 0.4258 0.6486 0.7176 0.035 Uiso 1 1 calc R . . C113 C 0.4114(5) 0.5603(3) 0.6417(3) 0.0261(12) Uani 1 1 d . . . C114 C 0.3818(5) 0.5465(3) 0.5722(3) 0.0250(12) Uani 1 1 d . . . H114 H 0.3844 0.4875 0.5547 0.030 Uiso 1 1 calc R . . C115 C -0.0449(4) 0.3726(3) 0.3823(2) 0.0227(12) Uani 1 1 d . . . C116 C -0.0119(5) 0.3453(3) 0.4511(3) 0.0270(13) Uani 1 1 d . . . H116 H 0.0029 0.3891 0.4847 0.032 Uiso 1 1 calc R . . C117 C -0.0009(5) 0.2551(3) 0.4699(3) 0.0274(13) Uani 1 1 d . . . H117 H 0.0227 0.2366 0.5164 0.033 Uiso 1 1 calc R . . C118 C -0.0240(5) 0.1904(3) 0.4212(3) 0.0292(14) Uani 1 1 d . . . C119 C -0.0539(5) 0.2169(3) 0.3518(3) 0.0272(13) Uani 1 1 d . . . H119 H -0.0665 0.1727 0.3182 0.033 Uiso 1 1 calc R . . C120 C -0.0651(5) 0.3080(3) 0.3326(3) 0.0253(12) Uani 1 1 d . . . H120 H -0.0864 0.3266 0.2857 0.030 Uiso 1 1 calc R . . C121 C -0.0316(6) 0.0350(3) 0.3981(3) 0.0436(16) Uani 1 1 d . . . H12A H -0.1193 0.0400 0.3804 0.065 Uiso 1 1 calc R . . H12B H -0.0170 -0.0243 0.4219 0.065 Uiso 1 1 calc R . . H12C H 0.0287 0.0418 0.3587 0.065 Uiso 1 1 calc R . . C201 C 0.6764(7) 0.3666(5) 0.0669(5) 0.075(2) Uani 1 1 d . . . C202 C 0.6845(6) 0.2722(6) 0.0907(4) 0.064(2) Uani 1 1 d . . . H202 H 0.6952 0.2546 0.1389 0.076 Uiso 1 1 calc R . . C203 C 0.6758(6) 0.2079(5) 0.0385(5) 0.068(2) Uani 1 1 d . . . H203 H 0.6789 0.1451 0.0509 0.081 Uiso 1 1 calc R . . C204 C 0.6630(7) 0.2368(6) -0.0284(5) 0.074(2) Uani 1 1 d . . . H204 H 0.6601 0.1935 -0.0636 0.088 Uiso 1 1 calc R . . C205 C 0.6545(8) 0.3222(7) -0.0471(5) 0.096(3) Uani 1 1 d . . . H205 H 0.6431 0.3390 -0.0953 0.115 Uiso 1 1 calc R . . C206 C 0.6611(7) 0.3855(5) -0.0022(5) 0.072(2) Uani 1 1 d . . . H206 H 0.6548 0.4469 -0.0188 0.086 Uiso 1 1 calc R . . C207 C 0.6818(6) 0.4356(7) 0.1161(5) 0.172(4) Uani 1 1 d . . . H20A H 0.7007 0.4930 0.0914 0.258 Uiso 1 1 calc R . . H20B H 0.7490 0.4198 0.1503 0.258 Uiso 1 1 calc R . . H20C H 0.5993 0.4415 0.1404 0.258 Uiso 1 1 calc R . . C301 C 0.3272(5) 0.1116(3) 0.4574(3) 0.0396(15) Uani 1 1 d . . . C302 C 0.3396(5) 0.1617(4) 0.5171(3) 0.0500(16) Uani 1 1 d . . . H302 H 0.3496 0.1307 0.5615 0.060 Uiso 1 1 calc R . . C303 C 0.3375(6) 0.2551(4) 0.5135(4) 0.0593(19) Uani 1 1 d . . . H303 H 0.3474 0.2879 0.5547 0.071 Uiso 1 1 calc R . . C304 C 0.3211(6) 0.2996(4) 0.4493(4) 0.0533(19) Uani 1 1 d . . . H304 H 0.3184 0.3638 0.4461 0.064 Uiso 1 1 calc R . . C305 C 0.3087(5) 0.2530(4) 0.3911(3) 0.0476(16) Uani 1 1 d . . . H305 H 0.2975 0.2848 0.3472 0.057 Uiso 1 1 calc R . . C306 C 0.3119(5) 0.1591(3) 0.3940(3) 0.0379(13) Uani 1 1 d . . . H306 H 0.3035 0.1275 0.3521 0.045 Uiso 1 1 calc R . . C307 C 0.3284(4) 0.0102(3) 0.4628(3) 0.0512(13) Uani 1 1 d . . . H30A H 0.2404 -0.0103 0.4635 0.077 Uiso 1 1 calc R . . H30B H 0.3716 -0.0114 0.5060 0.077 Uiso 1 1 calc R . . H30C H 0.3741 -0.0140 0.4222 0.077 Uiso 1 1 calc R . . N1 N 0.5627(4) -0.0054(3) -0.2005(2) 0.0336(11) Uani 1 1 d . . . N2 N 0.6365(4) -0.3280(3) -0.1389(2) 0.0313(11) Uani 1 1 d . . . N101 N 0.3637(4) 0.8063(3) 0.6548(2) 0.0323(10) Uani 1 1 d . . . N102 N 0.4446(4) 0.4784(3) 0.6869(3) 0.0359(12) Uani 1 1 d . . . O1 O 0.7442(3) -0.16617(19) 0.07743(16) 0.0248(8) Uani 1 1 d . . . O2 O 0.6479(3) -0.0276(2) 0.06470(17) 0.0302(9) Uani 1 1 d . . . O3 O 0.6597(3) -0.3876(2) -0.09383(19) 0.0419(10) Uani 1 1 d . . . O4 O 0.6207(3) -0.3429(2) -0.20164(19) 0.0403(9) Uani 1 1 d . . . O5 O 0.5523(3) 0.0710(2) -0.18023(19) 0.0369(10) Uani 1 1 d . . . O6 O 0.5548(3) -0.0271(2) -0.26248(17) 0.0458(9) Uani 1 1 d . . . O7 O 1.1209(3) 0.0116(2) 0.20340(18) 0.0338(9) Uani 1 1 d . . . O8 O 1.1138(3) -0.0225(2) 0.07619(18) 0.0311(9) Uani 1 1 d . . . O9 O 1.0087(4) 0.4094(2) 0.05367(18) 0.0364(10) Uani 1 1 d . . . O101 O 0.2532(3) 0.67450(19) 0.42359(16) 0.0253(8) Uani 1 1 d . . . O102 O 0.3496(3) 0.5348(2) 0.42733(17) 0.0286(8) Uani 1 1 d . . . O103 O 0.3420(4) 0.8710(2) 0.61447(19) 0.0401(10) Uani 1 1 d . . . O104 O 0.3753(3) 0.8101(2) 0.71907(18) 0.0423(9) Uani 1 1 d . . . O105 O 0.4344(3) 0.4042(2) 0.66237(18) 0.0363(9) Uani 1 1 d . . . O106 O 0.4811(3) 0.4913(2) 0.74594(18) 0.0511(11) Uani 1 1 d . . . O107 O -0.1256(3) 0.4995(2) 0.29232(17) 0.0311(9) Uani 1 1 d . . . O108 O -0.1177(3) 0.5332(2) 0.41947(18) 0.0324(9) Uani 1 1 d . . . O109 O -0.0133(3) 0.1032(2) 0.44572(18) 0.0330(9) Uani 1 1 d . . . S1 S 1.06025(12) 0.02380(8) 0.13561(7) 0.0285(3) Uani 1 1 d . . . S2 S -0.06353(12) 0.48781(8) 0.36003(7) 0.0281(3) Uani 1 1 d . . . Br1 Br 0.80112(5) 0.05276(3) 0.21057(3) 0.03571(15) Uani 1 1 d . . . Br2 Br 0.19330(5) 0.46588(3) 0.28136(3) 0.03055(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(3) 0.029(3) 0.034(3) -0.004(2) 0.000(2) -0.003(2) C2 0.020(3) 0.028(2) 0.027(3) -0.002(2) 0.001(2) -0.001(2) C3 0.037(3) 0.024(3) 0.020(3) -0.005(2) -0.002(2) 0.001(2) C4 0.021(3) 0.026(3) 0.029(3) -0.001(2) 0.001(2) -0.0054(19) C5 0.035(3) 0.027(2) 0.034(3) -0.002(2) -0.005(2) -0.004(2) C6 0.050(4) 0.036(3) 0.030(3) 0.000(2) 0.000(3) -0.008(2) C7 0.040(3) 0.024(3) 0.034(3) 0.000(2) -0.008(2) -0.006(2) C8 0.023(3) 0.020(3) 0.029(3) 0.001(2) -0.001(2) 0.000(2) C9 0.024(3) 0.024(3) 0.023(3) -0.003(2) 0.005(2) -0.004(2) C10 0.017(3) 0.021(2) 0.032(3) -0.001(2) 0.003(2) -0.0042(18) C11 0.026(3) 0.032(3) 0.025(3) 0.007(2) 0.003(2) -0.001(2) C12 0.023(3) 0.031(3) 0.027(3) -0.005(2) -0.001(2) -0.002(2) C13 0.017(3) 0.028(3) 0.031(3) -0.003(2) 0.000(2) 0.001(2) C14 0.019(3) 0.024(3) 0.025(3) 0.000(2) 0.001(2) -0.0018(19) C15 0.019(3) 0.020(2) 0.035(3) 0.001(2) 0.006(2) -0.0013(19) C16 0.027(3) 0.027(3) 0.029(3) -0.005(2) -0.004(2) -0.004(2) C17 0.024(3) 0.035(3) 0.027(3) -0.001(2) 0.000(2) -0.004(2) C18 0.021(3) 0.021(3) 0.033(3) -0.004(2) 0.003(2) -0.004(2) C19 0.028(3) 0.029(3) 0.029(3) -0.003(2) 0.002(3) -0.006(2) C20 0.028(3) 0.027(3) 0.024(3) 0.001(2) 0.003(2) -0.001(2) C21 0.065(4) 0.015(2) 0.042(3) -0.011(2) -0.008(3) 0.003(2) C101 0.026(3) 0.025(2) 0.023(3) -0.002(2) 0.000(2) 0.001(2) C102 0.031(3) 0.025(2) 0.026(3) -0.002(2) 0.002(2) 0.000(2) C103 0.021(3) 0.026(2) 0.021(3) -0.002(2) 0.001(2) 0.001(2) C104 0.035(3) 0.024(2) 0.024(3) 0.003(2) -0.001(2) -0.005(2) C105 0.032(3) 0.027(2) 0.030(3) 0.004(2) -0.002(2) -0.005(2) C106 0.036(3) 0.038(3) 0.026(3) 0.001(2) -0.005(2) -0.011(2) C107 0.034(3) 0.021(2) 0.041(3) 0.002(2) 0.001(2) 0.003(2) C108 0.017(3) 0.028(3) 0.027(3) -0.001(2) 0.002(2) -0.004(2) C109 0.018(3) 0.028(3) 0.028(3) 0.001(2) 0.001(2) -0.002(2) C110 0.023(3) 0.025(3) 0.031(3) 0.002(2) 0.004(2) 0.003(2) C111 0.027(3) 0.029(3) 0.026(3) -0.007(2) 0.001(2) -0.004(2) C112 0.022(3) 0.041(3) 0.024(3) 0.002(2) -0.003(2) -0.004(2) C113 0.021(3) 0.026(3) 0.031(3) 0.005(2) 0.003(2) -0.0029(19) C114 0.024(3) 0.023(2) 0.027(3) -0.002(2) 0.002(2) -0.0019(19) C115 0.022(3) 0.020(2) 0.026(3) 0.001(2) -0.002(2) -0.0011(19) C116 0.027(3) 0.024(3) 0.031(3) -0.005(2) 0.007(2) -0.004(2) C117 0.027(3) 0.034(3) 0.022(3) -0.004(2) -0.002(2) -0.002(2) C118 0.024(3) 0.021(3) 0.041(3) 0.006(3) 0.003(3) 0.003(2) C119 0.024(3) 0.027(3) 0.031(3) -0.005(2) 0.001(2) -0.004(2) C120 0.024(3) 0.028(3) 0.025(3) -0.001(2) -0.004(2) -0.007(2) C121 0.049(4) 0.026(3) 0.056(4) -0.001(3) 0.002(3) 0.003(2) C201 0.042(4) 0.081(6) 0.107(7) -0.070(5) 0.018(4) -0.013(4) C202 0.032(4) 0.111(6) 0.048(4) 0.005(4) -0.006(3) -0.011(4) C203 0.025(4) 0.047(4) 0.129(7) 0.019(5) 0.005(4) -0.003(3) C204 0.051(5) 0.084(6) 0.087(6) -0.009(4) 0.006(4) -0.022(4) C205 0.072(5) 0.130(8) 0.086(6) 0.006(6) -0.009(5) -0.010(5) C206 0.060(4) 0.063(5) 0.090(6) 0.017(5) 0.007(4) -0.001(4) C207 0.066(5) 0.236(11) 0.228(11) -0.158(9) 0.047(6) -0.045(6) C301 0.036(3) 0.038(3) 0.046(4) 0.003(3) -0.007(3) -0.007(2) C302 0.034(3) 0.072(4) 0.045(4) -0.001(3) -0.006(3) -0.011(3) C303 0.037(4) 0.053(4) 0.090(5) -0.026(4) 0.004(3) -0.002(3) C304 0.030(4) 0.033(3) 0.096(6) 0.005(4) 0.003(4) 0.005(3) C305 0.033(3) 0.045(4) 0.064(4) 0.002(3) 0.008(3) 0.007(3) C306 0.023(3) 0.039(3) 0.053(4) -0.016(3) 0.002(2) -0.002(2) C307 0.055(3) 0.041(3) 0.057(3) 0.000(3) -0.013(3) 0.001(2) N1 0.030(2) 0.031(3) 0.039(3) 0.006(2) 0.004(2) -0.0052(17) N2 0.029(3) 0.032(2) 0.033(3) -0.010(2) 0.003(2) 0.0003(19) N101 0.024(2) 0.037(2) 0.037(3) -0.010(2) -0.005(2) -0.0012(18) N102 0.027(2) 0.040(3) 0.040(3) 0.013(2) -0.005(2) -0.008(2) O1 0.026(2) 0.0244(17) 0.0239(19) -0.0006(15) -0.0026(16) 0.0011(14) O2 0.032(2) 0.0258(18) 0.033(2) -0.0026(16) -0.0046(17) -0.0015(14) O3 0.047(2) 0.0291(19) 0.049(2) 0.0015(17) -0.0037(17) 0.0026(16) O4 0.041(2) 0.045(2) 0.036(2) -0.0146(17) -0.0048(16) 0.0013(16) O5 0.046(2) 0.025(2) 0.039(2) 0.0031(18) 0.0034(17) 0.0013(16) O6 0.068(2) 0.042(2) 0.0269(19) -0.0012(17) -0.0100(17) -0.0064(17) O7 0.037(2) 0.0306(18) 0.035(2) 0.0018(16) -0.0115(18) -0.0048(15) O8 0.025(2) 0.0281(18) 0.041(2) -0.0102(16) 0.0079(17) -0.0001(14) O9 0.052(3) 0.0254(18) 0.031(2) -0.0014(16) -0.0030(18) 0.0046(16) O101 0.028(2) 0.0229(17) 0.0244(19) 0.0003(15) -0.0032(16) 0.0008(14) O102 0.027(2) 0.0250(18) 0.034(2) -0.0045(16) 0.0006(16) 0.0038(14) O103 0.048(2) 0.0295(19) 0.043(2) -0.0060(17) -0.0066(18) -0.0014(16) O104 0.045(2) 0.049(2) 0.034(2) -0.0178(16) -0.0087(17) 0.0018(16) O105 0.0373(19) 0.030(2) 0.041(2) 0.0086(17) 0.0022(16) -0.0021(15) O106 0.074(3) 0.049(2) 0.032(2) 0.0109(18) -0.0264(19) -0.0224(18) O107 0.029(2) 0.0302(17) 0.034(2) 0.0039(16) -0.0104(17) -0.0044(14) O108 0.031(2) 0.0292(18) 0.038(2) -0.0071(16) 0.0032(18) -0.0021(15) O109 0.036(2) 0.0249(18) 0.038(2) -0.0002(17) -0.0038(18) -0.0031(15) S1 0.0240(8) 0.0279(7) 0.0338(8) -0.0024(6) -0.0002(6) -0.0046(5) S2 0.0244(8) 0.0260(7) 0.0338(8) -0.0010(6) 0.0005(6) -0.0030(5) Br1 0.0333(4) 0.0357(3) 0.0396(3) -0.0157(3) 0.0077(3) -0.0075(2) Br2 0.0321(3) 0.0287(3) 0.0316(3) -0.0085(2) 0.0039(3) -0.0036(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.521(6) . ? C1 S1 1.805(5) . ? C1 Br1 1.943(5) . ? C1 H1 1.0000 . ? C2 C3 1.528(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O1 1.475(6) . ? C3 C4 1.542(6) . ? C3 H3 1.0000 . ? C4 C7 1.514(7) . ? C4 C5 1.543(7) . ? C4 C6 1.560(7) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O2 1.205(6) . ? C8 O1 1.344(5) . ? C8 C9 1.498(7) . ? C9 C14 1.375(7) . ? C9 C10 1.389(5) . ? C10 C11 1.389(7) . ? C10 H10 0.9500 . ? C11 C12 1.362(7) . ? C11 N1 1.493(5) . ? C12 C13 1.378(5) . ? C12 H12 0.9500 . ? C13 C14 1.392(7) . ? C13 N2 1.470(7) . ? C14 H14 0.9500 . ? C15 C20 1.390(7) . ? C15 C16 1.396(6) . ? C15 S1 1.749(4) . ? C16 C17 1.376(6) . ? C16 H16 0.9500 . ? C17 C18 1.381(7) . ? C17 H17 0.9500 . ? C18 O9 1.359(5) . ? C18 C19 1.405(6) . ? C19 C20 1.375(6) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 O9 1.442(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C101 C102 1.530(6) . ? C101 S2 1.800(5) . ? C101 Br2 1.941(5) . ? C101 H101 1.0000 . ? C102 C103 1.527(7) . ? C102 H10A 0.9900 . ? C102 H10B 0.9900 . ? C103 O101 1.479(6) . ? C103 C104 1.540(6) . ? C103 H103 1.0000 . ? C104 C107 1.520(7) . ? C104 C105 1.528(7) . ? C104 C106 1.549(7) . ? C105 H10C 0.9800 . ? C105 H10D 0.9800 . ? C105 H10E 0.9800 . ? C106 H10F 0.9800 . ? C106 H10G 0.9800 . ? C106 H10H 0.9800 . ? C107 H10I 0.9800 . ? C107 H10J 0.9800 . ? C107 H10K 0.9800 . ? C108 O102 1.208(6) . ? C108 O101 1.344(5) . ? C108 C109 1.483(7) . ? C109 C110 1.381(7) . ? C109 C114 1.401(5) . ? C110 C111 1.394(7) . ? C110 H110 0.9500 . ? C111 C112 1.385(6) . ? C111 N101 1.472(7) . ? C112 C113 1.341(7) . ? C112 H112 0.9500 . ? C113 C114 1.390(7) . ? C113 N102 1.491(5) . ? C114 H114 0.9500 . ? C115 C116 1.399(6) . ? C115 C120 1.401(7) . ? C115 S2 1.747(4) . ? C116 C117 1.370(6) . ? C116 H116 0.9500 . ? C117 C118 1.393(7) . ? C117 H117 0.9500 . ? C118 O109 1.356(5) . ? C118 C119 1.399(7) . ? C119 C120 1.385(6) . ? C119 H119 0.9500 . ? C120 H120 0.9500 . ? C121 O109 1.410(7) . ? C121 H12A 0.9800 . ? C121 H12B 0.9800 . ? C121 H12C 0.9800 . ? C201 C206 1.346(10) . ? C201 C207 1.421(10) . ? C201 C202 1.453(10) . ? C202 C203 1.415(11) . ? C202 H202 0.9500 . ? C203 C204 1.335(10) . ? C203 H203 0.9500 . ? C204 C205 1.301(9) . ? C204 H204 0.9500 . ? C205 C206 1.301(10) . ? C205 H205 0.9500 . ? C206 H206 0.9500 . ? C207 H20A 0.9800 . ? C207 H20B 0.9800 . ? C207 H20C 0.9800 . ? C301 C306 1.381(7) . ? C301 C302 1.396(8) . ? C301 C307 1.503(7) . ? C302 C303 1.384(8) . ? C302 H302 0.9500 . ? C303 C304 1.375(9) . ? C303 H303 0.9500 . ? C304 C305 1.342(9) . ? C304 H304 0.9500 . ? C305 C306 1.390(7) . ? C305 H305 0.9500 . ? C306 H306 0.9500 . ? C307 H30A 0.9800 . ? C307 H30B 0.9800 . ? C307 H30C 0.9800 . ? N1 O5 1.214(5) . ? N1 O6 1.244(5) . ? N2 O3 1.225(4) . ? N2 O4 1.240(5) . ? N101 O103 1.220(4) . ? N101 O104 1.236(5) . ? N102 O106 1.218(6) . ? N102 O105 1.222(6) . ? O7 S1 1.447(3) . ? O8 S1 1.449(4) . ? O107 S2 1.452(3) . ? O108 S2 1.445(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 C2 C1 S1 110.6(3) . . ? C2 C1 Br1 111.6(3) . . ? S1 C1 Br1 110.5(3) . . ? C2 C1 H1 108.0 . . ? S1 C1 H1 108.0 . . ? Br1 C1 H1 108.0 . . ? C1 C2 C3 113.4(3) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? O1 C3 C2 107.1(4) . . ? O1 C3 C4 106.3(4) . . ? C2 C3 C4 115.4(3) . . ? O1 C3 H3 109.3 . . ? C2 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? C7 C4 C3 112.5(4) . . ? C7 C4 C5 109.4(4) . . ? C3 C4 C5 108.2(3) . . ? C7 C4 C6 111.1(4) . . ? C3 C4 C6 107.3(4) . . ? C5 C4 C6 108.2(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 O1 125.0(5) . . ? O2 C8 C9 123.8(4) . . ? O1 C8 C9 111.2(4) . . ? C14 C9 C10 121.3(5) . . ? C14 C9 C8 121.9(4) . . ? C10 C9 C8 116.7(4) . . ? C11 C10 C9 117.4(5) . . ? C11 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? C12 C11 C10 123.6(4) . . ? C12 C11 N1 118.9(5) . . ? C10 C11 N1 117.5(5) . . ? C11 C12 C13 116.8(5) . . ? C11 C12 H12 121.6 . . ? C13 C12 H12 121.6 . . ? C12 C13 C14 122.6(5) . . ? C12 C13 N2 118.9(5) . . ? C14 C13 N2 118.5(4) . . ? C9 C14 C13 118.2(4) . . ? C9 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C20 C15 C16 120.2(4) . . ? C20 C15 S1 120.8(3) . . ? C16 C15 S1 119.0(4) . . ? C17 C16 C15 118.8(5) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 121.2(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? O9 C18 C17 115.5(4) . . ? O9 C18 C19 124.4(5) . . ? C17 C18 C19 120.1(4) . . ? C20 C19 C18 118.8(5) . . ? C20 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? C19 C20 C15 120.9(4) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? O9 C21 H21A 109.5 . . ? O9 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O9 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C102 C101 S2 111.4(3) . . ? C102 C101 Br2 110.9(3) . . ? S2 C101 Br2 110.9(3) . . ? C102 C101 H101 107.8 . . ? S2 C101 H101 107.8 . . ? Br2 C101 H101 107.8 . . ? C103 C102 C101 113.7(3) . . ? C103 C102 H10A 108.8 . . ? C101 C102 H10A 108.8 . . ? C103 C102 H10B 108.8 . . ? C101 C102 H10B 108.8 . . ? H10A C102 H10B 107.7 . . ? O101 C103 C102 107.6(4) . . ? O101 C103 C104 106.0(4) . . ? C102 C103 C104 116.5(3) . . ? O101 C103 H103 108.8 . . ? C102 C103 H103 108.8 . . ? C104 C103 H103 108.8 . . ? C107 C104 C105 110.0(4) . . ? C107 C104 C103 112.0(4) . . ? C105 C104 C103 109.0(3) . . ? C107 C104 C106 110.3(4) . . ? C105 C104 C106 108.2(4) . . ? C103 C104 C106 107.2(4) . . ? C104 C105 H10C 109.5 . . ? C104 C105 H10D 109.5 . . ? H10C C105 H10D 109.5 . . ? C104 C105 H10E 109.5 . . ? H10C C105 H10E 109.5 . . ? H10D C105 H10E 109.5 . . ? C104 C106 H10F 109.5 . . ? C104 C106 H10G 109.5 . . ? H10F C106 H10G 109.5 . . ? C104 C106 H10H 109.5 . . ? H10F C106 H10H 109.5 . . ? H10G C106 H10H 109.5 . . ? C104 C107 H10I 109.5 . . ? C104 C107 H10J 109.5 . . ? H10I C107 H10J 109.5 . . ? C104 C107 H10K 109.5 . . ? H10I C107 H10K 109.5 . . ? H10J C107 H10K 109.5 . . ? O102 C108 O101 125.6(5) . . ? O102 C108 C109 123.1(4) . . ? O101 C108 C109 111.2(4) . . ? C110 C109 C114 119.6(5) . . ? C110 C109 C108 123.8(4) . . ? C114 C109 C108 116.6(5) . . ? C109 C110 C111 119.1(4) . . ? C109 C110 H110 120.4 . . ? C111 C110 H110 120.4 . . ? C112 C111 C110 121.8(5) . . ? C112 C111 N101 119.5(5) . . ? C110 C111 N101 118.7(4) . . ? C113 C112 C111 117.8(5) . . ? C113 C112 H112 121.1 . . ? C111 C112 H112 121.1 . . ? C112 C113 C114 123.4(4) . . ? C112 C113 N102 119.8(5) . . ? C114 C113 N102 116.8(5) . . ? C113 C114 C109 118.3(5) . . ? C113 C114 H114 120.8 . . ? C109 C114 H114 120.8 . . ? C116 C115 C120 120.1(4) . . ? C116 C115 S2 119.2(4) . . ? C120 C115 S2 120.7(3) . . ? C117 C116 C115 119.8(5) . . ? C117 C116 H116 120.1 . . ? C115 C116 H116 120.1 . . ? C116 C117 C118 120.5(4) . . ? C116 C117 H117 119.7 . . ? C118 C117 H117 119.7 . . ? O109 C118 C117 115.6(4) . . ? O109 C118 C119 124.1(5) . . ? C117 C118 C119 120.2(4) . . ? C120 C119 C118 119.4(5) . . ? C120 C119 H119 120.3 . . ? C118 C119 H119 120.3 . . ? C119 C120 C115 119.9(4) . . ? C119 C120 H120 120.0 . . ? C115 C120 H120 120.0 . . ? O109 C121 H12A 109.5 . . ? O109 C121 H12B 109.5 . . ? H12A C121 H12B 109.5 . . ? O109 C121 H12C 109.5 . . ? H12A C121 H12C 109.5 . . ? H12B C121 H12C 109.5 . . ? C206 C201 C207 122.1(9) . . ? C206 C201 C202 117.8(7) . . ? C207 C201 C202 120.2(10) . . ? C203 C202 C201 116.5(6) . . ? C203 C202 H202 121.7 . . ? C201 C202 H202 121.7 . . ? C204 C203 C202 119.0(6) . . ? C204 C203 H203 120.5 . . ? C202 C203 H203 120.5 . . ? C205 C204 C203 122.2(9) . . ? C205 C204 H204 118.9 . . ? C203 C204 H204 118.9 . . ? C206 C205 C204 122.6(8) . . ? C206 C205 H205 118.7 . . ? C204 C205 H205 118.7 . . ? C205 C206 C201 121.9(7) . . ? C205 C206 H206 119.0 . . ? C201 C206 H206 119.0 . . ? C201 C207 H20A 109.5 . . ? C201 C207 H20B 109.5 . . ? H20A C207 H20B 109.5 . . ? C201 C207 H20C 109.5 . . ? H20A C207 H20C 109.5 . . ? H20B C207 H20C 109.5 . . ? C306 C301 C302 117.3(5) . . ? C306 C301 C307 121.8(6) . . ? C302 C301 C307 120.9(5) . . ? C303 C302 C301 121.9(5) . . ? C303 C302 H302 119.1 . . ? C301 C302 H302 119.1 . . ? C304 C303 C302 118.8(7) . . ? C304 C303 H303 120.6 . . ? C302 C303 H303 120.6 . . ? C305 C304 C303 120.4(6) . . ? C305 C304 H304 119.8 . . ? C303 C304 H304 119.8 . . ? C304 C305 C306 121.3(5) . . ? C304 C305 H305 119.4 . . ? C306 C305 H305 119.4 . . ? C301 C306 C305 120.3(6) . . ? C301 C306 H306 119.9 . . ? C305 C306 H306 119.9 . . ? C301 C307 H30A 109.5 . . ? C301 C307 H30B 109.5 . . ? H30A C307 H30B 109.5 . . ? C301 C307 H30C 109.5 . . ? H30A C307 H30C 109.5 . . ? H30B C307 H30C 109.5 . . ? O5 N1 O6 125.6(4) . . ? O5 N1 C11 118.2(5) . . ? O6 N1 C11 116.2(4) . . ? O3 N2 O4 123.4(4) . . ? O3 N2 C13 118.9(4) . . ? O4 N2 C13 117.7(4) . . ? O103 N101 O104 125.1(4) . . ? O103 N101 C111 118.2(4) . . ? O104 N101 C111 116.7(4) . . ? O106 N102 O105 125.1(4) . . ? O106 N102 C113 116.5(5) . . ? O105 N102 C113 118.4(5) . . ? C8 O1 C3 118.2(4) . . ? C18 O9 C21 117.7(4) . . ? C108 O101 C103 117.1(4) . . ? C118 O109 C121 117.9(4) . . ? O7 S1 O8 119.5(2) . . ? O7 S1 C15 108.8(2) . . ? O8 S1 C15 109.1(2) . . ? O7 S1 C1 109.4(2) . . ? O8 S1 C1 103.7(2) . . ? C15 S1 C1 105.2(2) . . ? O108 S2 O107 119.3(2) . . ? O108 S2 C115 108.8(2) . . ? O107 S2 C115 109.3(2) . . ? O108 S2 C101 104.0(2) . . ? O107 S2 C101 109.7(2) . . ? C115 S2 C101 104.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C1 C2 C3 -169.9(4) . . . . ? Br1 C1 C2 C3 66.6(5) . . . . ? C1 C2 C3 O1 78.2(5) . . . . ? C1 C2 C3 C4 -163.6(4) . . . . ? O1 C3 C4 C7 64.0(5) . . . . ? C2 C3 C4 C7 -54.6(6) . . . . ? O1 C3 C4 C5 -57.0(5) . . . . ? C2 C3 C4 C5 -175.6(4) . . . . ? O1 C3 C4 C6 -173.6(4) . . . . ? C2 C3 C4 C6 67.8(5) . . . . ? O2 C8 C9 C14 -163.2(5) . . . . ? O1 C8 C9 C14 16.7(7) . . . . ? O2 C8 C9 C10 18.5(7) . . . . ? O1 C8 C9 C10 -161.6(4) . . . . ? C14 C9 C10 C11 -1.3(7) . . . . ? C8 C9 C10 C11 177.0(5) . . . . ? C9 C10 C11 C12 2.6(8) . . . . ? C9 C10 C11 N1 -178.3(4) . . . . ? C10 C11 C12 C13 -2.0(7) . . . . ? N1 C11 C12 C13 179.0(4) . . . . ? C11 C12 C13 C14 0.0(7) . . . . ? C11 C12 C13 N2 -178.8(4) . . . . ? C10 C9 C14 C13 -0.5(7) . . . . ? C8 C9 C14 C13 -178.7(5) . . . . ? C12 C13 C14 C9 1.2(7) . . . . ? N2 C13 C14 C9 180.0(4) . . . . ? C20 C15 C16 C17 1.0(7) . . . . ? S1 C15 C16 C17 -179.7(4) . . . . ? C15 C16 C17 C18 -0.1(7) . . . . ? C16 C17 C18 O9 179.0(4) . . . . ? C16 C17 C18 C19 0.0(8) . . . . ? O9 C18 C19 C20 -179.8(5) . . . . ? C17 C18 C19 C20 -0.9(7) . . . . ? C18 C19 C20 C15 1.8(7) . . . . ? C16 C15 C20 C19 -1.9(7) . . . . ? S1 C15 C20 C19 178.8(4) . . . . ? S2 C101 C102 C103 168.7(3) . . . . ? Br2 C101 C102 C103 -67.2(5) . . . . ? C101 C102 C103 O101 -77.0(5) . . . . ? C101 C102 C103 C104 164.3(4) . . . . ? O101 C103 C104 C107 -66.6(5) . . . . ? C102 C103 C104 C107 53.0(6) . . . . ? O101 C103 C104 C105 55.3(5) . . . . ? C102 C103 C104 C105 175.0(4) . . . . ? O101 C103 C104 C106 172.2(4) . . . . ? C102 C103 C104 C106 -68.1(6) . . . . ? O102 C108 C109 C110 163.1(5) . . . . ? O101 C108 C109 C110 -18.5(7) . . . . ? O102 C108 C109 C114 -16.7(7) . . . . ? O101 C108 C109 C114 161.7(4) . . . . ? C114 C109 C110 C111 0.0(7) . . . . ? C108 C109 C110 C111 -179.9(5) . . . . ? C109 C110 C111 C112 0.1(8) . . . . ? C109 C110 C111 N101 -177.8(4) . . . . ? C110 C111 C112 C113 0.5(7) . . . . ? N101 C111 C112 C113 178.4(5) . . . . ? C111 C112 C113 C114 -1.4(8) . . . . ? C111 C112 C113 N102 -178.9(4) . . . . ? C112 C113 C114 C109 1.5(8) . . . . ? N102 C113 C114 C109 179.0(4) . . . . ? C110 C109 C114 C113 -0.7(7) . . . . ? C108 C109 C114 C113 179.1(5) . . . . ? C120 C115 C116 C117 -0.8(7) . . . . ? S2 C115 C116 C117 178.0(4) . . . . ? C115 C116 C117 C118 -0.8(7) . . . . ? C116 C117 C118 O109 -178.5(4) . . . . ? C116 C117 C118 C119 2.5(8) . . . . ? O109 C118 C119 C120 178.7(4) . . . . ? C117 C118 C119 C120 -2.4(7) . . . . ? C118 C119 C120 C115 0.8(7) . . . . ? C116 C115 C120 C119 0.9(7) . . . . ? S2 C115 C120 C119 -177.9(4) . . . . ? C206 C201 C202 C203 0.1(10) . . . . ? C207 C201 C202 C203 178.7(6) . . . . ? C201 C202 C203 C204 1.1(10) . . . . ? C202 C203 C204 C205 -2.1(11) . . . . ? C203 C204 C205 C206 1.8(13) . . . . ? C204 C205 C206 C201 -0.4(14) . . . . ? C207 C201 C206 C205 -179.1(8) . . . . ? C202 C201 C206 C205 -0.5(12) . . . . ? C306 C301 C302 C303 -0.5(9) . . . . ? C307 C301 C302 C303 -179.4(5) . . . . ? C301 C302 C303 C304 1.0(9) . . . . ? C302 C303 C304 C305 -0.8(9) . . . . ? C303 C304 C305 C306 0.1(10) . . . . ? C302 C301 C306 C305 -0.2(8) . . . . ? C307 C301 C306 C305 178.7(5) . . . . ? C304 C305 C306 C301 0.4(8) . . . . ? C12 C11 N1 O5 175.6(4) . . . . ? C10 C11 N1 O5 -3.6(7) . . . . ? C12 C11 N1 O6 -7.2(7) . . . . ? C10 C11 N1 O6 173.6(4) . . . . ? C12 C13 N2 O3 -177.4(4) . . . . ? C14 C13 N2 O3 3.8(7) . . . . ? C12 C13 N2 O4 3.7(7) . . . . ? C14 C13 N2 O4 -175.1(5) . . . . ? C112 C111 N101 O103 175.4(4) . . . . ? C110 C111 N101 O103 -6.6(7) . . . . ? C112 C111 N101 O104 -6.4(7) . . . . ? C110 C111 N101 O104 171.5(5) . . . . ? C112 C113 N102 O106 -8.5(7) . . . . ? C114 C113 N102 O106 173.8(5) . . . . ? C112 C113 N102 O105 172.0(5) . . . . ? C114 C113 N102 O105 -5.7(7) . . . . ? O2 C8 O1 C3 7.8(7) . . . . ? C9 C8 O1 C3 -172.1(4) . . . . ? C2 C3 O1 C8 -94.6(4) . . . . ? C4 C3 O1 C8 141.5(4) . . . . ? C17 C18 O9 C21 -178.2(5) . . . . ? C19 C18 O9 C21 0.8(7) . . . . ? O102 C108 O101 C103 -7.3(7) . . . . ? C109 C108 O101 C103 174.3(4) . . . . ? C102 C103 O101 C108 94.0(4) . . . . ? C104 C103 O101 C108 -140.7(4) . . . . ? C117 C118 O109 C121 -178.0(5) . . . . ? C119 C118 O109 C121 1.0(7) . . . . ? C20 C15 S1 O7 -11.9(5) . . . . ? C16 C15 S1 O7 168.9(4) . . . . ? C20 C15 S1 O8 -143.9(4) . . . . ? C16 C15 S1 O8 36.9(4) . . . . ? C20 C15 S1 C1 105.3(4) . . . . ? C16 C15 S1 C1 -73.9(4) . . . . ? C2 C1 S1 O7 -64.6(4) . . . . ? Br1 C1 S1 O7 59.5(2) . . . . ? C2 C1 S1 O8 64.0(4) . . . . ? Br1 C1 S1 O8 -171.88(19) . . . . ? C2 C1 S1 C15 178.7(3) . . . . ? Br1 C1 S1 C15 -57.3(3) . . . . ? C116 C115 S2 O108 -35.1(4) . . . . ? C120 C115 S2 O108 143.7(4) . . . . ? C116 C115 S2 O107 -166.9(4) . . . . ? C120 C115 S2 O107 11.9(5) . . . . ? C116 C115 S2 C101 75.6(4) . . . . ? C120 C115 S2 C101 -105.6(4) . . . . ? C102 C101 S2 O108 -61.3(4) . . . . ? Br2 C101 S2 O108 174.61(18) . . . . ? C102 C101 S2 O107 67.3(4) . . . . ? Br2 C101 S2 O107 -56.7(2) . . . . ? C102 C101 S2 C115 -175.5(3) . . . . ? Br2 C101 S2 C115 60.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.414 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.053