# 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 _publ_contact_author_name 'Min Shi' _publ_contact_author_email mshi@mail.sioc.ac.cn loop_ _publ_author_name 'Min Shi' 'Zhen Zhang' # Attachment '- cd21255.cif' data_cd21255 _database_code_depnum_ccdc_archive 'CCDC 868903' #TrackingRef '- cd21255.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25 Br N4 O7 S2' _chemical_formula_weight 625.51 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 11.0457(9) _cell_length_b 14.7223(15) _cell_length_c 36.520(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5938.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2281 _cell_measurement_theta_min 4.609 _cell_measurement_theta_max 38.289 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.265 _exptl_crystal_size_mid 0.228 _exptl_crystal_size_min 0.101 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 1.571 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.39276 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9942 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1414 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.12 _diffrn_reflns_theta_max 25.50 _reflns_number_total 9942 _reflns_number_gt 5209 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1468P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 9942 _refine_ls_number_parameters 668 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1553 _refine_ls_R_factor_gt 0.1004 _refine_ls_wR_factor_ref 0.2521 _refine_ls_wR_factor_gt 0.2259 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.001 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.008 0.750 0.337 421 286 ' ' 2 -0.005 0.250 0.837 421 286 ' ' _platon_squeeze_details ; ; 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 0.55751(12) 0.39497(9) 0.97933(5) 0.0683(4) Uani 1 1 d . . . Br1' Br 0.67483(12) 0.60112(10) 0.19069(5) 0.0716(5) Uani 1 1 d . . . S1 S 0.5424(3) 0.7440(2) 0.90911(10) 0.0528(10) Uani 1 1 d . . . S2 S 0.8133(2) 0.55431(19) 1.07361(7) 0.0358(6) Uani 1 1 d . . . S1' S 0.6876(3) 0.2547(2) 0.25812(9) 0.0453(8) Uani 1 1 d . . . S2' S 0.4160(2) 0.4470(2) 0.09473(8) 0.0395(7) Uani 1 1 d . . . N1 N 0.6282(8) 0.6549(6) 0.9157(3) 0.044(2) Uani 1 1 d . . . N2 N 0.6980(8) 0.6652(6) 0.9485(2) 0.039(2) Uani 1 1 d . . . H2A H 0.7411 0.7127 0.9528 0.046 Uiso 1 1 calc R . . N3 N 0.7196(8) 0.5611(6) 1.0398(3) 0.043(2) Uani 1 1 d . . . H3 H 0.6605 0.5233 1.0387 0.052 Uiso 1 1 calc R . . N4 N 1.2197(10) 0.3290(8) 1.0202(3) 0.062(3) Uani 1 1 d . . . N1' N 0.5977(9) 0.3449(7) 0.2526(3) 0.049(3) Uani 1 1 d . . . N2' N 0.5284(7) 0.3311(6) 0.2192(2) 0.036(2) Uani 1 1 d . . . H2'A H 0.4861 0.2833 0.2147 0.043 Uiso 1 1 calc R . . N3' N 0.5080(7) 0.4413(6) 0.1285(2) 0.041(2) Uani 1 1 d . . . H3' H 0.5641 0.4816 0.1304 0.049 Uiso 1 1 calc R . . N4' N 0.0104(10) 0.6781(9) 0.1489(3) 0.058(3) Uani 1 1 d . . . O1 O 0.7065(8) 0.7907(6) 1.0224(3) 0.062(3) Uani 1 1 d . . . O2 O 0.4794(8) 0.7324(6) 0.8757(3) 0.067(3) Uani 1 1 d . . . O3 O 0.4741(7) 0.7563(6) 0.9408(3) 0.070(3) Uani 1 1 d . . . O4 O 0.8584(7) 0.6423(5) 1.0810(2) 0.048(2) Uani 1 1 d . . . O5 O 0.7514(7) 0.5063(6) 1.10187(19) 0.046(2) Uani 1 1 d . . . O6 O 1.2954(8) 0.3657(8) 0.9994(4) 0.090(4) Uani 1 1 d . . . O7 O 1.2268(8) 0.2492(7) 1.0314(3) 0.072(3) Uani 1 1 d . . . O1' O 0.5181(8) 0.2145(6) 0.1460(2) 0.058(2) Uani 1 1 d . . . O2' O 0.7575(7) 0.2460(5) 0.2242(2) 0.048(2) Uani 1 1 d . . . O3' O 0.7512(8) 0.2763(9) 0.2920(3) 0.086(3) Uani 1 1 d . . . O4' O 0.3659(7) 0.3571(5) 0.0874(2) 0.048(2) Uani 1 1 d . . . O5' O 0.4766(7) 0.4973(6) 0.0660(2) 0.053(2) Uani 1 1 d . . . O6' O -0.0574(10) 0.6417(9) 0.1707(3) 0.091(3) Uani 1 1 d . . . O7' O 0.0042(9) 0.7528(6) 0.1377(3) 0.069(3) Uani 1 1 d . . . C1 C 0.6909(8) 0.5905(7) 0.9740(3) 0.035(3) Uani 1 1 d . . . H1 H 0.6054 0.5735 0.9761 0.042 Uiso 1 1 calc R . . C2 C 0.7317(9) 0.6281(7) 1.0116(3) 0.038(3) Uani 1 1 d . . . H2 H 0.8171 0.6455 1.0099 0.046 Uiso 1 1 calc R . . C3 C 0.6595(11) 0.7106(7) 1.0207(3) 0.044(3) Uani 1 1 d . . . C4 C 0.5275(11) 0.6998(9) 1.0283(4) 0.059(4) Uani 1 1 d . . . H4A H 0.5134 0.7048 1.0541 0.088 Uiso 1 1 calc R . . H4B H 0.5011 0.6413 1.0199 0.088 Uiso 1 1 calc R . . H4C H 0.4832 0.7464 1.0157 0.088 Uiso 1 1 calc R . . C5 C 0.7608(9) 0.5055(9) 0.9642(3) 0.047(3) Uani 1 1 d . . . C6 C 0.8919(10) 0.5156(8) 0.9516(3) 0.045(3) Uani 1 1 d . . . H6A H 0.9261 0.5730 0.9494 0.054 Uiso 1 1 calc R . . C7 C 0.9564(14) 0.4428(11) 0.9439(4) 0.071(4) Uani 1 1 d . . . H7A H 1.0393 0.4476 0.9398 0.085 Uiso 1 1 calc R . . C8 C 0.9001(17) 0.3593(9) 0.9419(4) 0.080(5) Uani 1 1 d . . . H8 H 0.9404 0.3104 0.9314 0.096 Uiso 1 1 calc R . . C9 C 0.7851(12) 0.3473(8) 0.9554(4) 0.064(4) Uani 1 1 d . . . H9 H 0.7537 0.2892 0.9584 0.076 Uiso 1 1 calc R . . C10 C 0.7213(11) 0.4175(8) 0.9640(3) 0.047(3) Uani 1 1 d . . . C11 C 0.7018(14) 0.6299(10) 0.8821(4) 0.070(4) Uani 1 1 d . . . H11A H 0.7744 0.6657 0.8815 0.105 Uiso 1 1 calc R . . H11B H 0.6550 0.6416 0.8605 0.105 Uiso 1 1 calc R . . H11C H 0.7226 0.5666 0.8831 0.105 Uiso 1 1 calc R . . C12 C 0.6419(11) 0.8365(9) 0.9045(4) 0.051(3) Uani 1 1 d . . . C13 C 0.6893(11) 0.8775(9) 0.9340(4) 0.054(3) Uani 1 1 d . . . H13 H 0.6685 0.8579 0.9574 0.065 Uiso 1 1 calc R . . C14 C 0.7704(11) 0.9500(10) 0.9296(4) 0.063(4) Uani 1 1 d . . . H14 H 0.8054 0.9778 0.9498 0.076 Uiso 1 1 calc R . . C15 C 0.7966(15) 0.9788(11) 0.8955(4) 0.082(5) Uani 1 1 d . . . C16 C 0.7533(15) 0.9328(10) 0.8652(4) 0.072(4) Uani 1 1 d . . . H16 H 0.7798 0.9476 0.8417 0.086 Uiso 1 1 calc R . . C17 C 0.6707(12) 0.8653(9) 0.8705(3) 0.053(3) Uani 1 1 d . . . H17 H 0.6336 0.8385 0.8504 0.064 Uiso 1 1 calc R . . C18 C 0.881(3) 1.0618(19) 0.8890(7) 0.190(15) Uani 1 1 d . . . H18A H 0.8405 1.1164 0.8964 0.285 Uiso 1 1 calc R . . H18B H 0.9015 1.0656 0.8635 0.285 Uiso 1 1 calc R . . H18C H 0.9539 1.0546 0.9031 0.285 Uiso 1 1 calc R . . C19 C 0.9341(8) 0.4868(7) 1.0573(3) 0.034(2) Uani 1 1 d . . . C20 C 1.0361(9) 0.5294(8) 1.0440(3) 0.040(3) Uani 1 1 d . . . H20 H 1.0426 0.5924 1.0444 0.048 Uiso 1 1 calc R . . C21 C 1.1298(9) 0.4757(8) 1.0300(3) 0.041(3) Uani 1 1 d . . . H21 H 1.1960 0.5014 1.0182 0.049 Uiso 1 1 calc R . . C22 C 1.1196(9) 0.3803(7) 1.0347(3) 0.041(3) Uani 1 1 d . . . C23 C 1.0219(10) 0.3418(9) 1.0482(3) 0.047(3) Uani 1 1 d . . . H23 H 1.0168 0.2789 1.0499 0.057 Uiso 1 1 calc R . . C24 C 0.9276(11) 0.3950(8) 1.0599(4) 0.052(3) Uani 1 1 d . . . H24 H 0.8587 0.3680 1.0697 0.063 Uiso 1 1 calc R . . C1' C 0.5397(9) 0.4081(7) 0.1943(3) 0.038(3) Uani 1 1 d . . . H1' H 0.6248 0.4265 0.1930 0.046 Uiso 1 1 calc R . . C2' C 0.4997(10) 0.3687(7) 0.1566(3) 0.036(3) Uani 1 1 d . . . H2' H 0.4136 0.3535 0.1589 0.043 Uiso 1 1 calc R . . C3' C 0.5649(10) 0.2805(9) 0.1457(3) 0.040(3) Uani 1 1 d . . . C4' C 0.7029(12) 0.2938(10) 0.1365(5) 0.073(4) Uani 1 1 d . . . H4'1 H 0.7462 0.2389 0.1420 0.110 Uiso 1 1 calc R . . H4'2 H 0.7349 0.3428 0.1509 0.110 Uiso 1 1 calc R . . H4'3 H 0.7118 0.3078 0.1109 0.110 Uiso 1 1 calc R . . C5' C 0.4596(6) 0.4937(4) 0.2054(2) 0.042(3) Uani 1 1 d G . . C6' C 0.3382(6) 0.4827(4) 0.2143(3) 0.055(3) Uani 1 1 d G . . H6' H 0.3034 0.4252 0.2137 0.065 Uiso 1 1 calc R . . C7' C 0.2688(6) 0.5576(6) 0.2241(3) 0.109(8) Uani 1 1 d G . . H7' H 0.1876 0.5502 0.2301 0.131 Uiso 1 1 calc R . . C8' C 0.3209(8) 0.6435(5) 0.2250(3) 0.084(5) Uani 1 1 d G . . H8' H 0.2745 0.6937 0.2315 0.101 Uiso 1 1 calc R . . C9' C 0.4423(8) 0.6545(4) 0.2160(3) 0.072(4) Uani 1 1 d G . . H9' H 0.4772 0.7120 0.2166 0.086 Uiso 1 1 calc R . . C10' C 0.5117(5) 0.5796(5) 0.2062(3) 0.051(3) Uani 1 1 d G . . C11' C 0.5238(14) 0.3731(11) 0.2832(3) 0.070(4) Uani 1 1 d . . . H11D H 0.4748 0.4240 0.2760 0.105 Uiso 1 1 calc R . . H11E H 0.5750 0.3904 0.3032 0.105 Uiso 1 1 calc R . . H11F H 0.4725 0.3238 0.2905 0.105 Uiso 1 1 calc R . . C12' C 0.5982(7) 0.1565(5) 0.2626(2) 0.043(3) Uani 1 1 d G . . C13' C 0.5372(8) 0.1196(6) 0.23285(19) 0.063(4) Uani 1 1 d G . . H13' H 0.5465 0.1451 0.2097 0.075 Uiso 1 1 calc R . . C14' C 0.4624(9) 0.0446(6) 0.2376(3) 0.087(5) Uani 1 1 d G . . H14' H 0.4217 0.0199 0.2177 0.105 Uiso 1 1 calc R . . C15' C 0.4486(9) 0.0065(6) 0.2722(3) 0.093(5) Uani 1 1 d G . . C16' C 0.5096(10) 0.0433(7) 0.3020(2) 0.090(5) Uani 1 1 d G . . H16' H 0.5004 0.0178 0.3251 0.108 Uiso 1 1 calc R . . C17' C 0.5844(8) 0.1184(7) 0.2972(2) 0.084(5) Uani 1 1 d G . . H17' H 0.6252 0.1430 0.3171 0.100 Uiso 1 1 calc R . . C18' C 0.378(2) -0.0805(16) 0.2831(8) 0.167(12) Uani 1 1 d . . . H18D H 0.4142 -0.1322 0.2713 0.250 Uiso 1 1 calc R . . H18E H 0.2954 -0.0749 0.2756 0.250 Uiso 1 1 calc R . . H18F H 0.3819 -0.0883 0.3092 0.250 Uiso 1 1 calc R . . C19' C 0.2959(9) 0.5117(7) 0.1089(3) 0.031(3) Uani 1 1 d . . . C20' C 0.1945(10) 0.4739(9) 0.1244(3) 0.047(3) Uani 1 1 d . . . H20' H 0.1911 0.4110 0.1264 0.057 Uiso 1 1 calc R . . C21' C 0.0948(9) 0.5248(8) 0.1374(4) 0.052(3) Uani 1 1 d . . . H21' H 0.0245 0.4982 0.1463 0.062 Uiso 1 1 calc R . . C22' C 0.1114(10) 0.6170(8) 0.1356(3) 0.043(3) Uani 1 1 d . . . C23' C 0.2112(11) 0.6625(8) 0.1210(4) 0.057(4) Uani 1 1 d . . . H23' H 0.2166 0.7255 0.1198 0.068 Uiso 1 1 calc R . . C24' C 0.3022(10) 0.6046(9) 0.1084(4) 0.052(3) Uani 1 1 d . . . H24' H 0.3721 0.6310 0.0990 0.063 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 Br1 0.0554(8) 0.0546(9) 0.0948(11) 0.0028(8) 0.0145(8) -0.0137(6) Br1' 0.0546(8) 0.0544(9) 0.1057(12) -0.0028(9) 0.0187(8) -0.0155(6) S1 0.0418(16) 0.053(2) 0.064(3) 0.0046(16) -0.0026(18) 0.0041(15) S2 0.0243(13) 0.0424(16) 0.0406(15) 0.0040(13) 0.0053(12) 0.0000(11) S1' 0.0515(17) 0.050(2) 0.0347(17) 0.0000(13) -0.0070(14) 0.0043(13) S2' 0.0336(15) 0.0435(17) 0.0416(16) 0.0021(13) 0.0033(13) -0.0011(12) N1 0.040(5) 0.037(6) 0.056(6) -0.009(5) -0.002(5) 0.008(4) N2 0.043(5) 0.028(5) 0.045(5) 0.007(4) -0.016(4) -0.009(4) N3 0.028(4) 0.038(6) 0.064(6) -0.003(5) -0.002(4) -0.007(4) N4 0.061(8) 0.040(7) 0.084(8) -0.021(6) -0.022(7) 0.014(6) N1' 0.062(7) 0.038(6) 0.046(6) -0.013(5) 0.007(5) -0.005(5) N2' 0.034(5) 0.037(6) 0.036(5) -0.009(4) 0.003(4) -0.005(4) N3' 0.022(4) 0.049(6) 0.052(6) 0.015(5) -0.002(4) -0.001(4) N4' 0.052(7) 0.077(10) 0.046(6) -0.006(6) 0.026(5) 0.001(6) O1 0.085(7) 0.025(5) 0.077(7) 0.016(4) 0.003(5) -0.001(4) O2 0.064(5) 0.055(6) 0.082(7) 0.018(5) -0.013(5) -0.007(4) O3 0.035(4) 0.060(7) 0.114(9) 0.002(5) -0.004(5) 0.006(4) O4 0.054(5) 0.033(5) 0.057(5) -0.012(4) -0.003(4) -0.001(4) O5 0.055(5) 0.054(5) 0.028(4) 0.006(3) 0.005(4) 0.014(4) O6 0.029(5) 0.105(9) 0.136(10) 0.007(8) 0.026(6) 0.024(5) O7 0.045(5) 0.072(9) 0.098(9) -0.015(6) -0.006(5) 0.014(5) O1' 0.069(6) 0.038(6) 0.067(6) 0.001(4) 0.014(5) 0.000(5) O2' 0.048(5) 0.051(6) 0.047(5) -0.002(4) 0.018(4) 0.011(4) O3' 0.050(5) 0.151(10) 0.057(6) -0.020(6) -0.030(5) 0.019(6) O4' 0.042(4) 0.050(5) 0.052(5) -0.002(4) -0.010(4) 0.001(4) O5' 0.035(4) 0.063(6) 0.061(6) 0.014(4) 0.011(4) 0.006(4) O6' 0.075(7) 0.096(9) 0.101(9) -0.032(7) 0.006(7) 0.019(6) O7' 0.076(6) 0.027(6) 0.105(9) -0.007(5) -0.008(6) 0.023(5) C1 0.019(5) 0.051(7) 0.036(6) -0.020(5) 0.003(5) 0.000(4) C2 0.025(6) 0.038(7) 0.051(7) 0.002(5) 0.006(5) -0.009(5) C3 0.071(8) 0.020(7) 0.040(7) 0.001(5) -0.001(6) -0.001(5) C4 0.059(8) 0.056(9) 0.061(8) 0.000(7) 0.021(7) 0.030(7) C5 0.032(6) 0.078(10) 0.029(6) 0.012(6) 0.002(5) 0.011(6) C6 0.051(7) 0.049(8) 0.034(6) 0.012(5) -0.007(5) 0.001(6) C7 0.067(9) 0.082(12) 0.063(9) 0.005(8) -0.007(7) 0.035(8) C8 0.135(15) 0.027(8) 0.078(10) -0.010(7) 0.030(10) 0.009(8) C9 0.060(8) 0.025(7) 0.105(11) -0.011(7) 0.018(8) -0.005(6) C10 0.052(7) 0.033(7) 0.056(7) 0.007(5) 0.011(6) -0.010(5) C11 0.090(11) 0.037(8) 0.082(11) -0.001(7) 0.011(9) -0.001(7) C12 0.049(7) 0.054(8) 0.051(8) 0.002(6) 0.004(6) 0.024(6) C13 0.052(8) 0.067(10) 0.044(8) -0.005(7) 0.009(6) 0.015(6) C14 0.051(8) 0.063(9) 0.076(10) -0.006(8) -0.025(7) -0.011(7) C15 0.105(13) 0.077(11) 0.064(10) 0.016(8) -0.011(9) -0.036(9) C16 0.110(12) 0.049(9) 0.056(9) 0.010(7) 0.010(8) -0.006(8) C17 0.073(9) 0.055(8) 0.032(6) -0.004(6) 0.002(6) -0.001(7) C18 0.25(3) 0.20(3) 0.122(18) 0.057(18) -0.024(19) -0.19(3) C19 0.022(5) 0.039(7) 0.042(6) 0.005(5) 0.008(5) 0.006(4) C20 0.029(5) 0.033(7) 0.058(8) 0.001(5) 0.003(5) 0.004(5) C21 0.028(6) 0.045(7) 0.051(7) 0.004(5) -0.001(5) 0.003(5) C22 0.030(6) 0.033(7) 0.061(7) -0.008(5) -0.012(5) 0.005(5) C23 0.038(6) 0.053(8) 0.050(7) 0.008(6) -0.004(6) 0.017(6) C24 0.048(7) 0.032(7) 0.077(9) -0.005(6) -0.025(7) -0.008(5) C1' 0.034(5) 0.027(6) 0.053(7) 0.008(5) 0.001(6) -0.003(4) C2' 0.037(6) 0.036(7) 0.033(6) 0.000(5) 0.012(5) -0.008(5) C3' 0.049(7) 0.040(8) 0.031(6) 0.005(6) 0.019(5) -0.005(6) C4' 0.056(8) 0.051(9) 0.113(13) 0.003(8) 0.029(8) 0.005(7) C5' 0.040(6) 0.028(6) 0.057(7) -0.011(5) 0.015(5) -0.002(5) C6' 0.035(6) 0.026(7) 0.102(11) -0.012(6) 0.010(6) -0.004(5) C7' 0.077(10) 0.077(12) 0.174(19) -0.068(12) 0.087(12) -0.051(9) C8' 0.080(11) 0.089(12) 0.083(11) -0.012(9) 0.047(9) 0.039(9) C9' 0.098(12) 0.045(9) 0.072(10) -0.008(7) 0.027(8) -0.001(8) C10' 0.050(7) 0.050(8) 0.054(8) -0.005(6) 0.005(6) -0.004(6) C11' 0.085(10) 0.092(12) 0.034(7) -0.008(7) 0.007(7) 0.019(9) C12' 0.026(5) 0.056(8) 0.048(7) 0.015(6) -0.008(5) -0.002(5) C13' 0.070(9) 0.065(10) 0.054(9) -0.007(7) -0.007(7) -0.014(7) C14' 0.135(15) 0.072(11) 0.056(9) 0.009(8) 0.022(10) -0.022(10) C15' 0.094(12) 0.079(12) 0.108(15) -0.002(11) 0.000(11) -0.020(9) C16' 0.093(12) 0.061(11) 0.115(14) 0.025(10) 0.009(11) -0.001(9) C17' 0.066(10) 0.093(14) 0.091(12) 0.032(10) -0.017(9) -0.017(8) C18' 0.18(2) 0.121(19) 0.20(3) -0.015(17) 0.08(2) -0.076(17) C19' 0.018(5) 0.027(6) 0.049(7) 0.007(5) -0.001(5) -0.006(4) C20' 0.040(7) 0.043(8) 0.059(8) -0.003(6) -0.008(6) 0.013(5) C21' 0.013(5) 0.048(8) 0.094(10) 0.010(7) 0.015(6) 0.008(5) C22' 0.033(6) 0.052(8) 0.044(7) -0.009(6) -0.007(5) 0.006(5) C23' 0.049(7) 0.021(7) 0.101(11) 0.005(6) 0.007(7) -0.008(5) C24' 0.033(6) 0.061(9) 0.064(8) 0.002(7) 0.023(6) -0.011(6) _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 Br1 C10 1.923(12) . ? Br1' C10' 1.915(6) . ? S1 O3 1.393(11) . ? S1 O2 1.416(10) . ? S1 N1 1.635(9) . ? S1 C12 1.759(14) . ? S2 O4 1.414(8) . ? S2 O5 1.426(8) . ? S2 N3 1.615(10) . ? S2 C19 1.767(10) . ? S1' O3' 1.457(9) . ? S1' O2' 1.464(8) . ? S1' N1' 1.671(11) . ? S1' C12' 1.759(7) . ? S2' O5' 1.447(9) . ? S2' O4' 1.460(8) . ? S2' N3' 1.600(9) . ? S2' C19' 1.712(11) . ? N1 N2 1.434(12) . ? N1 C11 1.517(17) . ? N2 C1 1.441(14) . ? N2 H2A 0.8600 . ? N3 C2 1.430(14) . ? N3 H3 0.8600 . ? N4 O7 1.246(14) . ? N4 O6 1.254(16) . ? N4 C22 1.439(16) . ? N1' C11' 1.442(16) . ? N1' N2' 1.454(13) . ? N2' C1' 1.459(14) . ? N2' H2'A 0.8600 . ? N3' C2' 1.485(13) . ? N3' H3' 0.8600 . ? N4' O7' 1.176(14) . ? N4' O6' 1.217(15) . ? N4' C22' 1.513(16) . ? O1 C3 1.291(14) . ? O1' C3' 1.100(14) . ? C1 C5 1.512(15) . ? C1 C2 1.550(15) . ? C1 H1 0.9800 . ? C2 C3 1.491(15) . ? C2 H2 0.9800 . ? C3 C4 1.492(17) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C10 1.367(16) . ? C5 C6 1.527(15) . ? C6 C7 1.318(17) . ? C6 H6A 0.9300 . ? C7 C8 1.38(2) . ? C7 H7A 0.9300 . ? C8 C9 1.37(2) . ? C8 H8 0.9300 . ? C9 C10 1.289(16) . ? C9 H9 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.341(17) . ? C12 C17 1.349(17) . ? C13 C14 1.402(18) . ? C13 H13 0.9300 . ? C14 C15 1.35(2) . ? C14 H14 0.9300 . ? C15 C16 1.38(2) . ? C15 C18 1.56(2) . ? C16 C17 1.363(19) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.357(15) . ? C19 C20 1.377(14) . ? C20 C21 1.400(15) . ? C20 H20 0.9300 . ? C21 C22 1.419(16) . ? C21 H21 0.9300 . ? C22 C23 1.315(16) . ? C23 C24 1.372(16) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C1' C2' 1.559(16) . ? C1' C5' 1.591(12) . ? C1' H1' 0.9800 . ? C2' C3' 1.538(16) . ? C2' H2' 0.9800 . ? C3' C4' 1.573(17) . ? C4' H4'1 0.9600 . ? C4' H4'2 0.9600 . ? C4' H4'3 0.9600 . ? C5' C6' 1.3900 . ? C5' C10' 1.3900 . ? C6' C7' 1.3900 . ? C6' H6' 0.9300 . ? C7' C8' 1.3900 . ? C7' H7' 0.9300 . ? C8' C9' 1.3900 . ? C8' H8' 0.9300 . ? C9' C10' 1.3900 . ? C9' H9' 0.9300 . ? C11' H11D 0.9600 . ? C11' H11E 0.9600 . ? C11' H11F 0.9600 . ? C12' C13' 1.3900 . ? C12' C17' 1.3900 . ? C13' C14' 1.3900 . ? C13' H13' 0.9300 . ? C14' C15' 1.3900 . ? C14' H14' 0.9300 . ? C15' C16' 1.3900 . ? C15' C18' 1.55(2) . ? C16' C17' 1.3900 . ? C16' H16' 0.9300 . ? C17' H17' 0.9300 . ? C18' H18D 0.9600 . ? C18' H18E 0.9600 . ? C18' H18F 0.9600 . ? C19' C24' 1.370(16) . ? C19' C20' 1.372(16) . ? C20' C21' 1.414(15) . ? C20' H20' 0.9300 . ? C21' C22' 1.371(17) . ? C21' H21' 0.9300 . ? C22' C23' 1.396(17) . ? C23' C24' 1.395(17) . ? C23' H23' 0.9300 . ? C24' H24' 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O2 117.8(6) . . ? O3 S1 N1 107.2(6) . . ? O2 S1 N1 108.4(6) . . ? O3 S1 C12 108.5(6) . . ? O2 S1 C12 108.5(6) . . ? N1 S1 C12 105.8(5) . . ? O4 S2 O5 119.0(5) . . ? O4 S2 N3 108.3(5) . . ? O5 S2 N3 106.1(5) . . ? O4 S2 C19 108.3(5) . . ? O5 S2 C19 109.1(5) . . ? N3 S2 C19 105.1(5) . . ? O3' S1' O2' 118.9(5) . . ? O3' S1' N1' 102.4(6) . . ? O2' S1' N1' 106.4(5) . . ? O3' S1' C12' 111.7(6) . . ? O2' S1' C12' 107.7(5) . . ? N1' S1' C12' 109.3(5) . . ? O5' S2' O4' 120.4(5) . . ? O5' S2' N3' 107.0(5) . . ? O4' S2' N3' 109.5(5) . . ? O5' S2' C19' 107.0(5) . . ? O4' S2' C19' 105.4(5) . . ? N3' S2' C19' 106.8(5) . . ? N2 N1 C11 114.4(9) . . ? N2 N1 S1 110.5(7) . . ? C11 N1 S1 112.7(9) . . ? N1 N2 C1 115.4(8) . . ? N1 N2 H2A 122.3 . . ? C1 N2 H2A 122.3 . . ? C2 N3 S2 122.2(7) . . ? C2 N3 H3 118.9 . . ? S2 N3 H3 118.9 . . ? O7 N4 O6 124.3(12) . . ? O7 N4 C22 115.1(13) . . ? O6 N4 C22 120.5(12) . . ? C11' N1' N2' 113.0(9) . . ? C11' N1' S1' 118.2(9) . . ? N2' N1' S1' 107.5(7) . . ? N1' N2' C1' 111.6(8) . . ? N1' N2' H2'A 124.2 . . ? C1' N2' H2'A 124.2 . . ? C2' N3' S2' 122.1(7) . . ? C2' N3' H3' 119.0 . . ? S2' N3' H3' 119.0 . . ? O7' N4' O6' 127.0(13) . . ? O7' N4' C22' 119.2(11) . . ? O6' N4' C22' 113.8(12) . . ? N2 C1 C5 116.9(9) . . ? N2 C1 C2 106.5(8) . . ? C5 C1 C2 110.8(9) . . ? N2 C1 H1 107.4 . . ? C5 C1 H1 107.4 . . ? C2 C1 H1 107.4 . . ? N3 C2 C3 110.6(9) . . ? N3 C2 C1 111.4(9) . . ? C3 C2 C1 109.4(9) . . ? N3 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C1 C2 H2 108.4 . . ? O1 C3 C2 122.7(11) . . ? O1 C3 C4 118.8(11) . . ? C2 C3 C4 118.5(10) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C10 C5 C1 128.6(10) . . ? C10 C5 C6 113.1(10) . . ? C1 C5 C6 118.3(10) . . ? C7 C6 C5 119.9(12) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C8 119.4(14) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C9 C8 C7 120.9(13) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 119.4(12) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C5 125.9(12) . . ? C9 C10 Br1 116.6(9) . . ? C5 C10 Br1 117.5(9) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 120.4(13) . . ? C13 C12 S1 121.0(11) . . ? C17 C12 S1 118.6(11) . . ? C12 C13 C14 119.9(12) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.0(13) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 120.8(13) . . ? C14 C15 C18 121.1(15) . . ? C16 C15 C18 118.0(15) . . ? C17 C16 C15 118.2(13) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C12 C17 C16 121.3(13) . . ? C12 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 121.4(10) . . ? C24 C19 S2 119.7(9) . . ? C20 C19 S2 118.7(8) . . ? C19 C20 C21 118.4(11) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C20 C21 C22 117.2(10) . . ? C20 C21 H21 121.4 . . ? C22 C21 H21 121.4 . . ? C23 C22 C21 122.4(10) . . ? C23 C22 N4 122.8(12) . . ? C21 C22 N4 114.5(11) . . ? C22 C23 C24 119.6(12) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C19 C24 C23 120.5(12) . . ? C19 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? N2' C1' C2' 103.7(8) . . ? N2' C1' C5' 114.2(9) . . ? C2' C1' C5' 111.2(8) . . ? N2' C1' H1' 109.2 . . ? C2' C1' H1' 109.2 . . ? C5' C1' H1' 109.2 . . ? N3' C2' C3' 113.6(8) . . ? N3' C2' C1' 109.0(8) . . ? C3' C2' C1' 114.3(9) . . ? N3' C2' H2' 106.5 . . ? C3' C2' H2' 106.5 . . ? C1' C2' H2' 106.5 . . ? O1' C3' C2' 121.5(10) . . ? O1' C3' C4' 124.6(13) . . ? C2' C3' C4' 113.8(11) . . ? C3' C4' H4'1 109.5 . . ? C3' C4' H4'2 109.5 . . ? H4'1 C4' H4'2 109.5 . . ? C3' C4' H4'3 109.5 . . ? H4'1 C4' H4'3 109.5 . . ? H4'2 C4' H4'3 109.5 . . ? C6' C5' C10' 120.0 . . ? C6' C5' C1' 120.2(6) . . ? C10' C5' C1' 119.8(6) . . ? C7' C6' C5' 120.0 . . ? C7' C6' H6' 120.0 . . ? C5' C6' H6' 120.0 . . ? C6' C7' C8' 120.0 . . ? C6' C7' H7' 120.0 . . ? C8' C7' H7' 120.0 . . ? C7' C8' C9' 120.0 . . ? C7' C8' H8' 120.0 . . ? C9' C8' H8' 120.0 . . ? C10' C9' C8' 120.0 . . ? C10' C9' H9' 120.0 . . ? C8' C9' H9' 120.0 . . ? C9' C10' C5' 120.0 . . ? C9' C10' Br1' 117.6(4) . . ? C5' C10' Br1' 122.2(4) . . ? N1' C11' H11D 109.5 . . ? N1' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? N1' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C13' C12' C17' 120.0 . . ? C13' C12' S1' 121.3(5) . . ? C17' C12' S1' 118.6(5) . . ? C12' C13' C14' 120.0 . . ? C12' C13' H13' 120.0 . . ? C14' C13' H13' 120.0 . . ? C15' C14' C13' 120.0 . . ? C15' C14' H14' 120.0 . . ? C13' C14' H14' 120.0 . . ? C14' C15' C16' 120.0 . . ? C14' C15' C18' 128.5(14) . . ? C16' C15' C18' 111.4(14) . . ? C15' C16' C17' 120.0 . . ? C15' C16' H16' 120.0 . . ? C17' C16' H16' 120.0 . . ? C16' C17' C12' 120.0 . . ? C16' C17' H17' 120.0 . . ? C12' C17' H17' 120.0 . . ? C15' C18' H18D 109.5 . . ? C15' C18' H18E 109.5 . . ? H18D C18' H18E 109.5 . . ? C15' C18' H18F 109.5 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? C24' C19' C20' 116.8(10) . . ? C24' C19' S2' 120.8(8) . . ? C20' C19' S2' 122.1(9) . . ? C19' C20' C21' 124.0(12) . . ? C19' C20' H20' 118.0 . . ? C21' C20' H20' 118.0 . . ? C22' C21' C20' 113.9(11) . . ? C22' C21' H21' 123.1 . . ? C20' C21' H21' 123.1 . . ? C21' C22' C23' 126.8(11) . . ? C21' C22' N4' 118.3(10) . . ? C23' C22' N4' 114.8(11) . . ? C24' C23' C22' 113.6(11) . . ? C24' C23' H23' 123.2 . . ? C22' C23' H23' 123.2 . . ? C19' C24' C23' 124.7(10) . . ? C19' C24' H24' 117.6 . . ? C23' C24' H24' 117.6 . . ? 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 O3 S1 N1 N2 -54.4(9) . . . . ? O2 S1 N1 N2 177.5(7) . . . . ? C12 S1 N1 N2 61.3(9) . . . . ? O3 S1 N1 C11 176.2(9) . . . . ? O2 S1 N1 C11 48.1(10) . . . . ? C12 S1 N1 C11 -68.2(10) . . . . ? C11 N1 N2 C1 -103.1(11) . . . . ? S1 N1 N2 C1 128.4(8) . . . . ? O4 S2 N3 C2 30.1(10) . . . . ? O5 S2 N3 C2 159.0(8) . . . . ? C19 S2 N3 C2 -85.5(9) . . . . ? O3' S1' N1' C11' -50.4(11) . . . . ? O2' S1' N1' C11' -175.9(10) . . . . ? C12' S1' N1' C11' 68.1(11) . . . . ? O3' S1' N1' N2' -179.9(8) . . . . ? O2' S1' N1' N2' 54.7(8) . . . . ? C12' S1' N1' N2' -61.3(8) . . . . ? C11' N1' N2' C1' 100.9(11) . . . . ? S1' N1' N2' C1' -126.8(8) . . . . ? O5' S2' N3' C2' -156.4(8) . . . . ? O4' S2' N3' C2' -24.4(10) . . . . ? C19' S2' N3' C2' 89.3(9) . . . . ? N1 N2 C1 C5 75.4(11) . . . . ? N1 N2 C1 C2 -160.2(8) . . . . ? S2 N3 C2 C3 -92.6(10) . . . . ? S2 N3 C2 C1 145.4(7) . . . . ? N2 C1 C2 N3 175.6(8) . . . . ? C5 C1 C2 N3 -56.2(11) . . . . ? N2 C1 C2 C3 53.0(10) . . . . ? C5 C1 C2 C3 -178.9(9) . . . . ? N3 C2 C3 O1 124.1(11) . . . . ? C1 C2 C3 O1 -112.8(11) . . . . ? N3 C2 C3 C4 -55.5(13) . . . . ? C1 C2 C3 C4 67.6(13) . . . . ? N2 C1 C5 C10 -130.6(12) . . . . ? C2 C1 C5 C10 107.1(12) . . . . ? N2 C1 C5 C6 47.1(12) . . . . ? C2 C1 C5 C6 -75.2(11) . . . . ? C10 C5 C6 C7 -3.8(15) . . . . ? C1 C5 C6 C7 178.2(11) . . . . ? C5 C6 C7 C8 9.7(18) . . . . ? C6 C7 C8 C9 -14(2) . . . . ? C7 C8 C9 C10 12(2) . . . . ? C8 C9 C10 C5 -7(2) . . . . ? C8 C9 C10 Br1 175.7(12) . . . . ? C1 C5 C10 C9 -180.0(13) . . . . ? C6 C5 C10 C9 2.2(18) . . . . ? C1 C5 C10 Br1 -2.3(16) . . . . ? C6 C5 C10 Br1 179.9(7) . . . . ? O3 S1 C12 C13 33.5(11) . . . . ? O2 S1 C12 C13 162.5(10) . . . . ? N1 S1 C12 C13 -81.3(11) . . . . ? O3 S1 C12 C17 -147.1(10) . . . . ? O2 S1 C12 C17 -18.0(12) . . . . ? N1 S1 C12 C17 98.1(11) . . . . ? C17 C12 C13 C14 -0.7(18) . . . . ? S1 C12 C13 C14 178.7(10) . . . . ? C12 C13 C14 C15 2(2) . . . . ? C13 C14 C15 C16 -6(2) . . . . ? C13 C14 C15 C18 177(2) . . . . ? C14 C15 C16 C17 9(3) . . . . ? C18 C15 C16 C17 -174(2) . . . . ? C13 C12 C17 C16 4(2) . . . . ? S1 C12 C17 C16 -175.7(11) . . . . ? C15 C16 C17 C12 -8(2) . . . . ? O4 S2 C19 C24 157.6(9) . . . . ? O5 S2 C19 C24 26.6(11) . . . . ? N3 S2 C19 C24 -86.8(10) . . . . ? O4 S2 C19 C20 -18.7(11) . . . . ? O5 S2 C19 C20 -149.6(9) . . . . ? N3 S2 C19 C20 96.9(10) . . . . ? C24 C19 C20 C21 5.9(18) . . . . ? S2 C19 C20 C21 -177.9(8) . . . . ? C19 C20 C21 C22 -7.8(16) . . . . ? C20 C21 C22 C23 6.6(17) . . . . ? C20 C21 C22 N4 -179.0(10) . . . . ? O7 N4 C22 C23 -21.8(17) . . . . ? O6 N4 C22 C23 161.5(12) . . . . ? O7 N4 C22 C21 163.8(10) . . . . ? O6 N4 C22 C21 -12.9(17) . . . . ? C21 C22 C23 C24 -2.9(18) . . . . ? N4 C22 C23 C24 -176.9(11) . . . . ? C20 C19 C24 C23 -2.2(19) . . . . ? S2 C19 C24 C23 -178.3(9) . . . . ? C22 C23 C24 C19 0.6(18) . . . . ? N1' N2' C1' C2' 161.3(8) . . . . ? N1' N2' C1' C5' -77.6(10) . . . . ? S2' N3' C2' C3' 84.8(11) . . . . ? S2' N3' C2' C1' -146.6(8) . . . . ? N2' C1' C2' N3' -179.6(8) . . . . ? C5' C1' C2' N3' 57.2(10) . . . . ? N2' C1' C2' C3' -51.4(10) . . . . ? C5' C1' C2' C3' -174.6(8) . . . . ? N3' C2' C3' O1' -126.3(12) . . . . ? C1' C2' C3' O1' 107.8(13) . . . . ? N3' C2' C3' C4' 56.8(13) . . . . ? C1' C2' C3' C4' -69.1(12) . . . . ? N2' C1' C5' C6' -48.1(11) . . . . ? C2' C1' C5' C6' 68.8(10) . . . . ? N2' C1' C5' C10' 131.5(7) . . . . ? C2' C1' C5' C10' -111.5(8) . . . . ? C10' C5' C6' C7' 0.0 . . . . ? C1' C5' C6' C7' 179.6(9) . . . . ? C5' C6' C7' C8' 0.0 . . . . ? C6' C7' C8' C9' 0.0 . . . . ? C7' C8' C9' C10' 0.0 . . . . ? C8' C9' C10' C5' 0.0 . . . . ? C8' C9' C10' Br1' 175.4(7) . . . . ? C6' C5' C10' C9' 0.0 . . . . ? C1' C5' C10' C9' -179.6(9) . . . . ? C6' C5' C10' Br1' -175.2(7) . . . . ? C1' C5' C10' Br1' 5.2(9) . . . . ? O3' S1' C12' C13' -174.9(6) . . . . ? O2' S1' C12' C13' -42.7(7) . . . . ? N1' S1' C12' C13' 72.5(7) . . . . ? O3' S1' C12' C17' 8.2(7) . . . . ? O2' S1' C12' C17' 140.4(6) . . . . ? N1' S1' C12' C17' -104.4(6) . . . . ? C17' C12' C13' C14' 0.0 . . . . ? S1' C12' C13' C14' -176.8(7) . . . . ? C12' C13' C14' C15' 0.0 . . . . ? C13' C14' C15' C16' 0.0 . . . . ? C13' C14' C15' C18' -175.0(17) . . . . ? C14' C15' C16' C17' 0.0 . . . . ? C18' C15' C16' C17' 175.8(14) . . . . ? C15' C16' C17' C12' 0.0 . . . . ? C13' C12' C17' C16' 0.0 . . . . ? S1' C12' C17' C16' 176.9(7) . . . . ? O5' S2' C19' C24' -32.5(12) . . . . ? O4' S2' C19' C24' -161.8(10) . . . . ? N3' S2' C19' C24' 81.8(11) . . . . ? O5' S2' C19' C20' 153.8(9) . . . . ? O4' S2' C19' C20' 24.5(11) . . . . ? N3' S2' C19' C20' -91.9(10) . . . . ? C24' C19' C20' C21' 4.2(18) . . . . ? S2' C19' C20' C21' 178.1(10) . . . . ? C19' C20' C21' C22' -4.3(18) . . . . ? C20' C21' C22' C23' 3.2(19) . . . . ? C20' C21' C22' N4' -179.9(10) . . . . ? O7' N4' C22' C21' -156.4(12) . . . . ? O6' N4' C22' C21' 23.3(16) . . . . ? O7' N4' C22' C23' 20.9(17) . . . . ? O6' N4' C22' C23' -159.4(12) . . . . ? C21' C22' C23' C24' -2(2) . . . . ? N4' C22' C23' C24' -179.1(11) . . . . ? C20' C19' C24' C23' -2.9(19) . . . . ? S2' C19' C24' C23' -176.9(11) . . . . ? C22' C23' C24' C19' 2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3' H3' Br1' 0.86 3.07 3.754(10) 137.7 . N3' H3' O5 0.86 2.35 3.014(12) 134.9 1_554 N2' H2'A O2' 0.86 2.59 3.206(11) 129.9 3_455 N3 H3 Br1 0.86 3.09 3.750(9) 135.2 . N3 H3 O5' 0.86 2.30 3.002(12) 139.4 1_556 N2 H2A O3 0.86 2.65 3.275(12) 130.4 3_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.652 _refine_diff_density_min -0.799 _refine_diff_density_rms 0.222 # Attachment '- cd21283.cif' data_cd21283 _database_code_depnum_ccdc_archive 'CCDC 870326' #TrackingRef '- cd21283.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Br N4 O4 S' _chemical_formula_weight 453.32 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 7.5819(7) _cell_length_b 9.2830(9) _cell_length_c 13.8365(14) _cell_angle_alpha 95.425(2) _cell_angle_beta 95.329(2) _cell_angle_gamma 106.406(2) _cell_volume 922.70(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2263 _cell_measurement_theta_min 4.611 _cell_measurement_theta_max 51.407 _exptl_crystal_description prisamatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.390 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.196 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 2.373 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1934 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6041 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4011 _reflns_number_gt 3208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0669P)^2^+0.4855P] 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 4011 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.38129(5) 0.23388(4) 0.35061(3) 0.06141(16) Uani 1 1 d . . . S1 S 0.74592(10) 0.21633(10) 0.03915(5) 0.0457(2) Uani 1 1 d . . . O1 O 0.9361(3) 0.2909(3) 0.03287(17) 0.0572(6) Uani 1 1 d . . . O2 O 0.6277(3) 0.1306(3) -0.04609(16) 0.0612(7) Uani 1 1 d . . . O3 O 0.5028(5) 0.7929(4) 0.2445(3) 0.0914(10) Uani 1 1 d . . . O4 O 0.2342(5) 0.6294(4) 0.2072(3) 0.0943(11) Uani 1 1 d . . . N1 N 0.7384(4) 0.1010(3) 0.11957(18) 0.0424(6) Uani 1 1 d D . . N2 N 0.9402(4) -0.0004(3) 0.3281(2) 0.0466(6) Uani 1 1 d . . . N3 N 0.8612(3) 0.1010(3) 0.37713(18) 0.0397(5) Uani 1 1 d . . . N4 N 0.4010(5) 0.6686(4) 0.2083(3) 0.0621(8) Uani 1 1 d . . . C1 C 0.8591(4) 0.1429(3) 0.2125(2) 0.0368(6) Uani 1 1 d . . . H1 H 0.9581 0.2360 0.2092 0.044 Uiso 1 1 calc R . . C2 C 0.9441(4) 0.0217(3) 0.2391(3) 0.0435(7) Uani 1 1 d . . . C3 C 0.7622(4) 0.1641(3) 0.3035(2) 0.0334(6) Uani 1 1 d . . . H3A H 0.6321 0.1028 0.2908 0.040 Uiso 1 1 calc R . . C4 C 1.0416(6) -0.0527(5) 0.1694(3) 0.0663(11) Uani 1 1 d . . . H4A H 1.0915 -0.1224 0.2016 0.100 Uiso 1 1 calc R . . H4B H 1.1405 0.0230 0.1485 0.100 Uiso 1 1 calc R . . H4C H 0.9554 -0.1064 0.1136 0.100 Uiso 1 1 calc R . . C5 C 0.7530(5) 0.0351(4) 0.4515(3) 0.0523(8) Uani 1 1 d . . . H5A H 0.6517 -0.0499 0.4214 0.079 Uiso 1 1 calc R . . H5B H 0.7055 0.1095 0.4841 0.079 Uiso 1 1 calc R . . H5C H 0.8300 0.0021 0.4982 0.079 Uiso 1 1 calc R . . C6 C 0.7729(4) 0.3254(3) 0.3403(2) 0.0366(6) Uani 1 1 d . . . C7 C 0.9490(5) 0.4361(4) 0.3558(2) 0.0479(7) Uani 1 1 d . . . H7 H 1.0536 0.4086 0.3420 0.057 Uiso 1 1 calc R . . C8 C 0.9662(6) 0.5833(4) 0.3909(3) 0.0617(10) Uani 1 1 d . . . H8 H 1.0823 0.6548 0.3998 0.074 Uiso 1 1 calc R . . C9 C 0.8143(7) 0.6260(4) 0.4128(3) 0.0675(11) Uani 1 1 d . . . H9 H 0.8275 0.7263 0.4361 0.081 Uiso 1 1 calc R . . C10 C 0.6438(6) 0.5220(4) 0.4005(3) 0.0612(10) Uani 1 1 d . . . H10 H 0.5411 0.5510 0.4161 0.073 Uiso 1 1 calc R . . C11 C 0.6232(5) 0.3718(4) 0.3643(2) 0.0441(7) Uani 1 1 d . . . C12 C 0.6452(4) 0.3546(4) 0.0842(2) 0.0423(7) Uani 1 1 d . . . C13 C 0.7568(4) 0.4954(4) 0.1283(3) 0.0501(8) Uani 1 1 d . . . H13 H 0.8849 0.5198 0.1304 0.060 Uiso 1 1 calc R . . C14 C 0.6765(5) 0.5989(4) 0.1689(3) 0.0516(8) Uani 1 1 d . . . H14 H 0.7493 0.6929 0.2001 0.062 Uiso 1 1 calc R . . C15 C 0.4871(5) 0.5600(4) 0.1623(2) 0.0499(8) Uani 1 1 d . . . C16 C 0.3732(4) 0.4227(4) 0.1164(3) 0.0527(8) Uani 1 1 d . . . H16 H 0.2450 0.4008 0.1119 0.063 Uiso 1 1 calc R . . C17 C 0.4539(4) 0.3188(4) 0.0772(3) 0.0521(8) Uani 1 1 d . . . H17 H 0.3803 0.2249 0.0462 0.063 Uiso 1 1 calc R . . H1A H 0.639(3) 0.034(3) 0.123(3) 0.046(9) Uiso 1 1 d 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 Br1 0.0464(2) 0.0754(3) 0.0713(3) 0.0160(2) 0.02137(17) 0.02540(18) S1 0.0353(4) 0.0605(5) 0.0302(4) -0.0016(3) 0.0029(3) -0.0011(3) O1 0.0383(12) 0.0773(16) 0.0450(13) 0.0007(11) 0.0098(10) 0.0002(11) O2 0.0486(13) 0.0846(18) 0.0325(12) -0.0087(11) 0.0005(10) -0.0025(12) O3 0.081(2) 0.074(2) 0.113(3) -0.0135(19) -0.0221(19) 0.0315(18) O4 0.066(2) 0.081(2) 0.141(3) 0.016(2) 0.030(2) 0.0251(16) N1 0.0373(13) 0.0445(14) 0.0342(13) -0.0058(11) 0.0009(10) -0.0012(11) N2 0.0417(14) 0.0400(14) 0.0617(18) 0.0063(12) 0.0080(12) 0.0171(11) N3 0.0430(13) 0.0380(13) 0.0398(13) 0.0048(10) 0.0053(10) 0.0147(10) N4 0.063(2) 0.060(2) 0.068(2) 0.0164(16) -0.0009(16) 0.0248(16) C1 0.0318(13) 0.0350(14) 0.0384(15) -0.0036(11) 0.0025(11) 0.0045(11) C2 0.0344(14) 0.0386(15) 0.0558(19) -0.0016(14) 0.0088(13) 0.0097(12) C3 0.0303(13) 0.0330(13) 0.0340(14) -0.0028(11) -0.0002(10) 0.0081(10) C4 0.062(2) 0.063(2) 0.083(3) 0.000(2) 0.031(2) 0.0271(19) C5 0.063(2) 0.0504(19) 0.0476(19) 0.0134(15) 0.0113(16) 0.0190(16) C6 0.0474(16) 0.0330(14) 0.0286(13) -0.0004(11) 0.0008(11) 0.0130(12) C7 0.0576(19) 0.0402(16) 0.0436(17) -0.0021(13) 0.0033(14) 0.0141(14) C8 0.079(3) 0.0386(18) 0.053(2) -0.0027(15) 0.0002(18) 0.0007(17) C9 0.111(4) 0.0369(18) 0.055(2) -0.0004(16) 0.014(2) 0.025(2) C10 0.097(3) 0.056(2) 0.0477(19) 0.0099(16) 0.0258(19) 0.044(2) C11 0.0529(18) 0.0443(16) 0.0403(16) 0.0087(13) 0.0117(13) 0.0198(14) C12 0.0376(15) 0.0509(17) 0.0308(14) 0.0100(13) -0.0001(11) 0.0007(13) C13 0.0327(15) 0.056(2) 0.0510(18) 0.0121(15) -0.0056(13) -0.0027(13) C14 0.0449(17) 0.0449(18) 0.057(2) 0.0099(15) -0.0087(15) 0.0038(14) C15 0.0475(18) 0.0527(19) 0.0483(18) 0.0183(15) -0.0019(14) 0.0114(15) C16 0.0341(15) 0.062(2) 0.056(2) 0.0144(17) -0.0004(14) 0.0040(15) C17 0.0368(16) 0.055(2) 0.0505(19) 0.0070(15) -0.0047(14) -0.0053(14) _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 Br1 C11 1.898(3) . ? S1 O1 1.427(2) . ? S1 O2 1.432(2) . ? S1 N1 1.609(3) . ? S1 C12 1.763(4) . ? O3 N4 1.222(4) . ? O4 N4 1.212(4) . ? N1 C1 1.459(4) . ? N1 H1A 0.838(18) . ? N2 C2 1.269(4) . ? N2 N3 1.406(3) . ? N3 C5 1.448(4) . ? N3 C3 1.471(4) . ? N4 C15 1.475(5) . ? C1 C2 1.503(4) . ? C1 C3 1.540(4) . ? C1 H1 0.9800 . ? C2 C4 1.499(4) . ? C3 C6 1.512(4) . ? C3 H3A 0.9800 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C11 1.379(4) . ? C6 C7 1.420(5) . ? C7 C8 1.371(5) . ? C7 H7 0.9300 . ? C8 C9 1.370(6) . ? C8 H8 0.9300 . ? C9 C10 1.362(6) . ? C9 H9 0.9300 . ? C10 C11 1.396(5) . ? C10 H10 0.9300 . ? C12 C17 1.385(4) . ? C12 C13 1.388(4) . ? C13 C14 1.378(5) . ? C13 H13 0.9300 . ? C14 C15 1.370(5) . ? C14 H14 0.9300 . ? C15 C16 1.377(5) . ? C16 C17 1.376(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.94(14) . . ? O1 S1 N1 107.85(15) . . ? O2 S1 N1 106.19(15) . . ? O1 S1 C12 107.59(15) . . ? O2 S1 C12 107.50(15) . . ? N1 S1 C12 107.16(14) . . ? C1 N1 S1 122.1(2) . . ? C1 N1 H1A 113(2) . . ? S1 N1 H1A 119(2) . . ? C2 N2 N3 109.9(3) . . ? N2 N3 C5 112.7(2) . . ? N2 N3 C3 108.4(2) . . ? C5 N3 C3 115.2(2) . . ? O4 N4 O3 124.2(4) . . ? O4 N4 C15 118.0(3) . . ? O3 N4 C15 117.8(3) . . ? N1 C1 C2 113.1(2) . . ? N1 C1 C3 115.4(2) . . ? C2 C1 C3 100.6(2) . . ? N1 C1 H1 109.1 . . ? C2 C1 H1 109.1 . . ? C3 C1 H1 109.1 . . ? N2 C2 C4 123.7(3) . . ? N2 C2 C1 113.4(3) . . ? C4 C2 C1 122.6(3) . . ? N3 C3 C6 110.0(2) . . ? N3 C3 C1 102.4(2) . . ? C6 C3 C1 116.0(2) . . ? N3 C3 H3A 109.4 . . ? C6 C3 H3A 109.4 . . ? C1 C3 H3A 109.4 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 117.2(3) . . ? C11 C6 C3 124.3(3) . . ? C7 C6 C3 118.5(3) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 120.7(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.0(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C6 C11 C10 121.3(3) . . ? C6 C11 Br1 121.4(2) . . ? C10 C11 Br1 117.3(3) . . ? C17 C12 C13 120.8(3) . . ? C17 C12 S1 119.0(3) . . ? C13 C12 S1 120.2(2) . . ? C14 C13 C12 119.6(3) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 118.5(3) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C14 C15 C16 123.0(3) . . ? C14 C15 N4 118.6(3) . . ? C16 C15 N4 118.4(3) . . ? C17 C16 C15 118.3(3) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C16 C17 C12 119.8(3) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? 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 O1 S1 N1 C1 42.8(3) . . . . ? O2 S1 N1 C1 172.5(2) . . . . ? C12 S1 N1 C1 -72.8(3) . . . . ? C2 N2 N3 C5 145.3(3) . . . . ? C2 N2 N3 C3 16.6(3) . . . . ? S1 N1 C1 C2 -135.3(2) . . . . ? S1 N1 C1 C3 109.6(3) . . . . ? N3 N2 C2 C4 171.7(3) . . . . ? N3 N2 C2 C1 -2.0(3) . . . . ? N1 C1 C2 N2 -136.0(3) . . . . ? C3 C1 C2 N2 -12.3(3) . . . . ? N1 C1 C2 C4 50.3(4) . . . . ? C3 C1 C2 C4 173.9(3) . . . . ? N2 N3 C3 C6 -147.0(2) . . . . ? C5 N3 C3 C6 85.8(3) . . . . ? N2 N3 C3 C1 -23.1(3) . . . . ? C5 N3 C3 C1 -150.3(3) . . . . ? N1 C1 C3 N3 142.3(2) . . . . ? C2 C1 C3 N3 20.3(3) . . . . ? N1 C1 C3 C6 -97.9(3) . . . . ? C2 C1 C3 C6 140.1(2) . . . . ? N3 C3 C6 C11 -112.1(3) . . . . ? C1 C3 C6 C11 132.4(3) . . . . ? N3 C3 C6 C7 64.9(3) . . . . ? C1 C3 C6 C7 -50.7(4) . . . . ? C11 C6 C7 C8 -1.6(5) . . . . ? C3 C6 C7 C8 -178.7(3) . . . . ? C6 C7 C8 C9 0.8(6) . . . . ? C7 C8 C9 C10 0.4(6) . . . . ? C8 C9 C10 C11 -0.7(6) . . . . ? C7 C6 C11 C10 1.2(5) . . . . ? C3 C6 C11 C10 178.2(3) . . . . ? C7 C6 C11 Br1 -178.3(2) . . . . ? C3 C6 C11 Br1 -1.3(4) . . . . ? C9 C10 C11 C6 -0.1(5) . . . . ? C9 C10 C11 Br1 179.4(3) . . . . ? O1 S1 C12 C17 166.1(3) . . . . ? O2 S1 C12 C17 35.6(3) . . . . ? N1 S1 C12 C17 -78.2(3) . . . . ? O1 S1 C12 C13 -15.8(3) . . . . ? O2 S1 C12 C13 -146.2(3) . . . . ? N1 S1 C12 C13 100.0(3) . . . . ? C17 C12 C13 C14 2.4(5) . . . . ? S1 C12 C13 C14 -175.7(3) . . . . ? C12 C13 C14 C15 -1.5(5) . . . . ? C13 C14 C15 C16 -0.4(5) . . . . ? C13 C14 C15 N4 178.2(3) . . . . ? O4 N4 C15 C14 -175.5(4) . . . . ? O3 N4 C15 C14 4.9(5) . . . . ? O4 N4 C15 C16 3.2(5) . . . . ? O3 N4 C15 C16 -176.5(4) . . . . ? C14 C15 C16 C17 1.4(5) . . . . ? N4 C15 C16 C17 -177.2(3) . . . . ? C15 C16 C17 C12 -0.5(5) . . . . ? C13 C12 C17 C16 -1.4(5) . . . . ? S1 C12 C17 C16 176.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2 0.838(18) 2.26(2) 3.009(3) 149(3) 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.922 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.074 # Attachment '- cd212307.cif' data_cd212307 _database_code_depnum_ccdc_archive 'CCDC 892218' #TrackingRef '- cd212307.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Br N4 O4 S' _chemical_formula_weight 453.32 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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 53.632(4) _cell_length_b 9.3905(6) _cell_length_c 16.7335(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.327(2) _cell_angle_gamma 90.00 _cell_volume 8233.2(9) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4195 _cell_measurement_theta_min 4.795 _cell_measurement_theta_max 39.415 _exptl_crystal_description 4195 _exptl_crystal_colour colorless _exptl_crystal_size_max 0.312 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.147 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3680 _exptl_absorpt_coefficient_mu 2.127 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.12906 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14905 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1017 _diffrn_reflns_limit_h_min -64 _diffrn_reflns_limit_h_max 63 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 0.78 _diffrn_reflns_theta_max 25.50 _reflns_number_total 14905 _reflns_number_gt 8759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0559P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.012(7) _chemical_absolute_configuration ad _refine_ls_number_reflns 14905 _refine_ls_number_parameters 1020 _refine_ls_number_restraints 795 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1254 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.076 0.000 209 45 ' ' 2 0.000 0.009 0.500 137 37 ' ' 3 0.500 -0.190 0.500 137 37 ' ' 4 0.500 0.576 1.000 209 45 ' ' 5 0.163 0.437 0.845 7 0 ' ' 6 0.837 0.437 0.155 7 0 ' ' 7 0.337 0.937 0.155 7 0 ' ' 8 0.663 0.937 0.845 7 0 ' ' _platon_squeeze_details ; ; 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 0.025861(15) 0.43786(9) 0.69145(5) 0.0920(3) Uani 1 1 d . . . Br2 Br 0.836500(16) 0.41438(11) 0.36479(6) 0.1122(3) Uani 1 1 d . . . Br3 Br 0.902711(12) 0.71880(8) 0.80064(4) 0.0722(2) Uani 1 1 d . . . S1 S 0.03870(3) 1.00069(18) 0.76631(11) 0.0741(5) Uani 1 1 d U . . S2 S 0.92052(4) 0.4185(2) 0.54861(11) 0.0862(6) Uani 1 1 d U . . S3 S 0.84391(3) 0.68457(17) 0.95936(9) 0.0579(4) Uani 1 1 d U . . S4 S 0.79019(3) 0.2380(2) 0.84393(9) 0.0660(4) Uani 1 1 d U . . N1 N 0.05101(9) 0.8508(5) 0.7959(3) 0.0606(13) Uani 1 1 d U . . H1A H 0.0600 0.8094 0.7658 0.073 Uiso 1 1 calc R . . N2 N 0.05711(9) 0.5617(6) 0.9380(3) 0.0664(14) Uani 1 1 d U . . N3 N 0.07691(10) 0.6573(7) 0.9717(3) 0.0696(15) Uani 1 1 d U . . N4 N -0.07271(10) 0.9107(7) 0.6489(4) 0.0691(14) Uani 1 1 d U . . N5 N 0.90772(10) 0.5287(6) 0.4774(3) 0.0697(14) Uani 1 1 d U . . H5 H 0.8975 0.5933 0.4879 0.084 Uiso 1 1 calc R . . N6 N 0.91776(10) 0.6852(6) 0.2978(3) 0.0693(14) Uani 1 1 d U . . N7 N 0.89970(10) 0.5840(6) 0.2610(3) 0.0637(14) Uani 1 1 d U . . N8 N 0.86573(17) -0.1263(9) 0.4551(5) 0.102(2) Uani 1 1 d U . . N9 N 0.86640(8) 0.5736(5) 0.9542(3) 0.0519(12) Uani 1 1 d U . . H9 H 0.8816 0.5934 0.9800 0.062 Uiso 1 1 calc R . . N10 N 0.87857(9) 0.2134(6) 0.9186(3) 0.0633(13) Uani 1 1 d U . . N11 N 0.88020(9) 0.2679(5) 0.8409(3) 0.0626(13) Uani 1 1 d U . . N12 N 0.81303(14) 0.9760(8) 0.6376(4) 0.0876(18) Uani 1 1 d U . . N13 N 0.77282(9) 0.2722(5) 0.9072(3) 0.0579(12) Uani 1 1 d U . . H13 H 0.7699 0.2053 0.9390 0.069 Uiso 1 1 calc R . . N14 N 0.74103(11) 0.5209(6) 1.0063(3) 0.0765(16) Uani 1 1 d U B . N15 N 0.72474(10) 0.5340(6) 0.9258(4) 0.0811(17) Uani 1 1 d U B . N16 N 0.72705(15) 0.0430(12) 0.5284(6) 0.120(3) Uani 1 1 d U . . O1 O 0.04890(9) 1.0383(6) 0.6952(3) 0.0925(15) Uani 1 1 d U . . O2 O 0.04111(10) 1.0950(5) 0.8345(3) 0.1022(18) Uani 1 1 d U . . O3 O -0.07997(9) 0.8083(6) 0.6005(3) 0.0840(14) Uani 1 1 d U . . O4 O -0.08709(9) 0.9920(6) 0.6712(3) 0.0898(14) Uani 1 1 d U . . O5 O 0.94626(11) 0.3986(7) 0.5431(4) 0.121(2) Uani 1 1 d U . . O6 O 0.91466(13) 0.4687(7) 0.6232(3) 0.124(2) Uani 1 1 d U . . O7 O 0.87445(18) -0.2049(8) 0.4140(6) 0.174(4) Uani 1 1 d U . . O8 O 0.84665(17) -0.1467(8) 0.4833(5) 0.146(3) Uani 1 1 d U . . O9 O 0.85479(8) 0.7870(5) 1.0177(2) 0.0737(12) Uani 1 1 d U . . O10 O 0.82203(8) 0.6048(5) 0.9688(3) 0.0743(12) Uani 1 1 d U . . O11 O 0.82262(13) 1.0909(7) 0.6277(3) 0.1114(18) Uani 1 1 d U . . O12 O 0.79654(14) 0.9214(8) 0.5863(3) 0.122(2) Uani 1 1 d U . . O13 O 0.80249(9) 0.3669(6) 0.8276(3) 0.0969(18) Uani 1 1 d U . . O14 O 0.80463(10) 0.1171(7) 0.8739(3) 0.1093(19) Uani 1 1 d U . . O15 O 0.71506(17) -0.0642(13) 0.5296(4) 0.179(4) Uani 1 1 d U . . O16 O 0.72841(16) 0.1083(12) 0.4658(4) 0.170(4) Uani 1 1 d U . . C1 C 0.04824(10) 0.7791(6) 0.8701(3) 0.0530(14) Uani 1 1 d U . . H1 H 0.0340 0.8217 0.8900 0.064 Uiso 1 1 calc R . . C2 C 0.04392(10) 0.6171(7) 0.8597(3) 0.0524(14) Uani 1 1 d U . . H2 H 0.0527 0.5833 0.8176 0.063 Uiso 1 1 calc R . . C3 C 0.07204(12) 0.7811(7) 0.9379(4) 0.0600(15) Uani 1 1 d U . . C4 C 0.08713(13) 0.9086(7) 0.9646(4) 0.085(2) Uani 1 1 d U . . H4A H 0.0981 0.8914 1.0170 0.128 Uiso 1 1 calc R . . H4B H 0.0759 0.9867 0.9688 0.128 Uiso 1 1 calc R . . H4C H 0.0973 0.9315 0.9256 0.128 Uiso 1 1 calc R . . C5 C 0.06705(14) 0.4213(8) 0.9347(5) 0.095(2) Uani 1 1 d U . . H5A H 0.0787 0.4202 0.8985 0.142 Uiso 1 1 calc R . . H5B H 0.0533 0.3564 0.9150 0.142 Uiso 1 1 calc R . . H5C H 0.0758 0.3929 0.9885 0.142 Uiso 1 1 calc R . . C6 C 0.01666(11) 0.5701(7) 0.8370(4) 0.0624(16) Uani 1 1 d U . . C7 C 0.00023(13) 0.6035(11) 0.8888(4) 0.101(3) Uani 1 1 d U . . H7 H 0.0066 0.6500 0.9379 0.122 Uiso 1 1 calc R . . C8 C -0.02507(15) 0.5686(12) 0.8680(5) 0.119(3) Uani 1 1 d U . . H8A H -0.0357 0.5918 0.9033 0.143 Uiso 1 1 calc R . . C9 C -0.03509(14) 0.4995(9) 0.7955(6) 0.095(2) Uani 1 1 d U . . H9A H -0.0524 0.4776 0.7816 0.114 Uiso 1 1 calc R . . C10 C -0.01949(13) 0.4639(7) 0.7446(4) 0.0720(18) Uani 1 1 d U . . H10 H -0.0263 0.4175 0.6957 0.086 Uiso 1 1 calc R . . C11 C 0.00592(11) 0.4946(7) 0.7635(3) 0.0613(16) Uani 1 1 d U . . C12 C 0.00518(12) 0.9673(7) 0.7324(4) 0.0667(17) Uani 1 1 d U . . C13 C -0.01166(15) 1.0735(7) 0.7427(5) 0.084(2) Uani 1 1 d U . . H13A H -0.0056 1.1584 0.7683 0.101 Uiso 1 1 calc R . . C14 C -0.03719(14) 1.0527(7) 0.7150(4) 0.0752(19) Uani 1 1 d U . . H14 H -0.0486 1.1238 0.7217 0.090 Uiso 1 1 calc R . . C15 C -0.04586(11) 0.9298(7) 0.6782(3) 0.0570(14) Uani 1 1 d U . . C16 C -0.02873(13) 0.8228(7) 0.6678(4) 0.0663(17) Uani 1 1 d U . . H16A H -0.0347 0.7378 0.6420 0.080 Uiso 1 1 calc R . . C17 C -0.00328(12) 0.8440(7) 0.6957(4) 0.0614(16) Uani 1 1 d U . . H17 H 0.0083 0.7732 0.6894 0.074 Uiso 1 1 calc R . . C18 C 0.91305(12) 0.5210(7) 0.3967(3) 0.0641(16) Uani 1 1 d U . . H18 H 0.9244 0.4398 0.3949 0.077 Uiso 1 1 calc R . . C19 C 0.89053(11) 0.5092(7) 0.3260(3) 0.0564(15) Uani 1 1 d U . . H19 H 0.8763 0.5636 0.3392 0.068 Uiso 1 1 calc R . . C20 C 0.92601(12) 0.6574(7) 0.3727(4) 0.0643(16) Uani 1 1 d U . . C21 C 0.94697(13) 0.7312(10) 0.4281(4) 0.092(2) Uani 1 1 d U . . H21A H 0.9616 0.6695 0.4408 0.138 Uiso 1 1 calc R . . H21B H 0.9417 0.7563 0.4776 0.138 Uiso 1 1 calc R . . H21C H 0.9514 0.8159 0.4021 0.138 Uiso 1 1 calc R . . C22 C 0.88000(15) 0.6507(9) 0.1980(4) 0.094(2) Uani 1 1 d U . . H22A H 0.8703 0.7163 0.2233 0.141 Uiso 1 1 calc R . . H22B H 0.8689 0.5786 0.1695 0.141 Uiso 1 1 calc R . . H22C H 0.8879 0.7009 0.1601 0.141 Uiso 1 1 calc R . . C23 C 0.88118(12) 0.3604(6) 0.3004(4) 0.0580(15) Uani 1 1 d U . . C24 C 0.89664(13) 0.2725(7) 0.2640(4) 0.0685(17) Uani 1 1 d U . . H24 H 0.9122 0.3053 0.2554 0.082 Uiso 1 1 calc R . . C25 C 0.88829(17) 0.1343(9) 0.2406(4) 0.087(2) Uani 1 1 d U . . H25 H 0.8988 0.0735 0.2188 0.105 Uiso 1 1 calc R . . C26 C 0.86499(18) 0.0882(8) 0.2495(5) 0.089(2) Uani 1 1 d U . . H26 H 0.8593 -0.0015 0.2302 0.107 Uiso 1 1 calc R . . C27 C 0.84991(15) 0.1715(9) 0.2861(5) 0.087(2) Uani 1 1 d U . . H27 H 0.8342 0.1376 0.2930 0.104 Uiso 1 1 calc R . . C28 C 0.85797(12) 0.3075(7) 0.3134(4) 0.0641(16) Uani 1 1 d U . . C29 C 0.90436(13) 0.2547(7) 0.5219(3) 0.0660(17) Uani 1 1 d U . . C30 C 0.91416(14) 0.1586(8) 0.4779(5) 0.079(2) Uani 1 1 d U . . H30 H 0.9299 0.1748 0.4643 0.095 Uiso 1 1 calc R . . C31 C 0.90069(16) 0.0353(8) 0.4529(4) 0.080(2) Uani 1 1 d U . . H31 H 0.9066 -0.0309 0.4200 0.096 Uiso 1 1 calc R . . C32 C 0.87915(15) 0.0147(8) 0.4772(5) 0.0757(19) Uani 1 1 d U . . C33 C 0.86924(15) 0.1085(9) 0.5228(5) 0.081(2) Uani 1 1 d U . . H33 H 0.8541 0.0897 0.5396 0.097 Uiso 1 1 calc R . . C34 C 0.88238(13) 0.2328(8) 0.5433(4) 0.0747(18) Uani 1 1 d U . . H34 H 0.8758 0.3024 0.5725 0.090 Uiso 1 1 calc R . . C35 C 0.86217(9) 0.4414(6) 0.9080(3) 0.0465(13) Uani 1 1 d U . . H35 H 0.8442 0.4382 0.8797 0.056 Uiso 1 1 calc R . . C36 C 0.87839(10) 0.4214(6) 0.8440(3) 0.0527(13) Uani 1 1 d U . . H36 H 0.8954 0.4607 0.8654 0.063 Uiso 1 1 calc R . . C37 C 0.86813(11) 0.3070(7) 0.9556(3) 0.0534(15) Uani 1 1 d U . . C38 C 0.86011(14) 0.2784(9) 1.0312(4) 0.093(2) Uani 1 1 d U . . H38A H 0.8592 0.1774 1.0389 0.139 Uiso 1 1 calc R . . H38B H 0.8436 0.3197 1.0288 0.139 Uiso 1 1 calc R . . H38C H 0.8722 0.3191 1.0761 0.139 Uiso 1 1 calc R . . C39 C 0.90347(16) 0.2174(11) 0.8183(6) 0.113(3) Uani 1 1 d U . . H39A H 0.9170 0.2139 0.8661 0.169 Uiso 1 1 calc R . . H39B H 0.9080 0.2813 0.7790 0.169 Uiso 1 1 calc R . . H39C H 0.9006 0.1239 0.7950 0.169 Uiso 1 1 calc R . . C40 C 0.86772(10) 0.4866(6) 0.7619(3) 0.0494(14) Uani 1 1 d U . . C41 C 0.84803(11) 0.4143(7) 0.7100(3) 0.0619(16) Uani 1 1 d U . . H41 H 0.8422 0.3286 0.7270 0.074 Uiso 1 1 calc R . . C42 C 0.83691(13) 0.4683(8) 0.6329(4) 0.0749(19) Uani 1 1 d U . . H42 H 0.8235 0.4198 0.5997 0.090 Uiso 1 1 calc R . . C43 C 0.84581(13) 0.5938(10) 0.6056(4) 0.082(2) Uani 1 1 d U . . H43 H 0.8389 0.6281 0.5535 0.099 Uiso 1 1 calc R . . C44 C 0.86546(13) 0.6685(8) 0.6580(4) 0.077(2) Uani 1 1 d U . . H44 H 0.8713 0.7549 0.6420 0.092 Uiso 1 1 calc R . . C45 C 0.87593(11) 0.6104(7) 0.7344(3) 0.0587(16) Uani 1 1 d U . . C46 C 0.83511(10) 0.7712(6) 0.8644(3) 0.0564(15) Uani 1 1 d U . . C47 C 0.84690(11) 0.8993(6) 0.8519(4) 0.0595(15) Uani 1 1 d U . . H47 H 0.8593 0.9397 0.8931 0.071 Uiso 1 1 calc R . . C48 C 0.83947(12) 0.9651(7) 0.7752(4) 0.0637(16) Uani 1 1 d U . . H48 H 0.8470 1.0503 0.7646 0.076 Uiso 1 1 calc R . . C49 C 0.82180(12) 0.9055(7) 0.7182(4) 0.0601(16) Uani 1 1 d U . . C50 C 0.80990(11) 0.7790(8) 0.7279(4) 0.0672(17) Uani 1 1 d U . . H50 H 0.7974 0.7421 0.6857 0.081 Uiso 1 1 calc R . . C51 C 0.81675(11) 0.7090(8) 0.8003(4) 0.0695(17) Uani 1 1 d U . . H51 H 0.8095 0.6214 0.8078 0.083 Uiso 1 1 calc R . . C52 C 0.76160(11) 0.4108(7) 0.9139(3) 0.0575(15) Uani 1 1 d U . . H52 H 0.7711 0.4819 0.8897 0.069 Uiso 1 1 calc R . . C53 C 0.73354(11) 0.4256(7) 0.8749(3) 0.0654(16) Uani 1 1 d DU . . H53 H 0.7246 0.3353 0.8778 0.098 Uiso 0.70 1 calc PR A 1 H53' H 0.7274 0.3294 0.8745 0.098 Uiso 0.30 1 d PR A 2 C54 C 0.76146(12) 0.4552(7) 1.0003(4) 0.0630(16) Uani 1 1 d U . . C55 C 0.78325(12) 0.4327(9) 1.0706(4) 0.080(2) Uani 1 1 d U . . H55A H 0.7795 0.4760 1.1186 0.119 Uiso 1 1 calc R . . H55B H 0.7983 0.4752 1.0587 0.119 Uiso 1 1 calc R . . H55C H 0.7860 0.3325 1.0797 0.119 Uiso 1 1 calc R . . C56 C 0.69811(14) 0.5165(13) 0.9331(6) 0.131(4) Uani 1 1 d U . . H56A H 0.6939 0.4170 0.9320 0.197 Uiso 1 1 calc R B . H56B H 0.6870 0.5639 0.8883 0.197 Uiso 1 1 calc R . . H56C H 0.6959 0.5572 0.9838 0.197 Uiso 1 1 calc R . . Br4 Br 0.69141(2) 0.25111(14) 0.74767(8) 0.1248(4) Uani 0.86 1 d PU B 1 C57 C 0.7292(2) 0.4791(14) 0.7829(5) 0.066(4) Uani 0.70 1 d PGDU B 1 C58 C 0.74303(18) 0.5922(13) 0.7606(6) 0.084(4) Uani 0.70 1 d PGU B 1 H58 H 0.7551 0.6390 0.8001 0.101 Uiso 0.70 1 calc PR B 1 C59 C 0.73879(19) 0.6355(11) 0.6794(7) 0.111(4) Uani 0.75 1 d PGU B 1 H59 H 0.7480 0.7113 0.6646 0.133 Uiso 0.75 1 calc PR B 1 C60 C 0.7208(2) 0.5657(13) 0.6205(5) 0.102(5) Uani 0.65 1 d PGU B 1 H60 H 0.7179 0.5947 0.5661 0.123 Uiso 0.65 1 calc PR B 1 C61 C 0.70696(19) 0.4525(12) 0.6427(5) 0.102(4) Uani 0.75 1 d PGU B 1 H61 H 0.6949 0.4058 0.6032 0.122 Uiso 0.75 1 calc PR B 1 C62 C 0.7112(2) 0.4092(11) 0.7239(6) 0.086(3) Uani 0.75 1 d PGU B 1 Br4' Br 0.74790(14) 0.7010(8) 0.8074(4) 0.111(2) Uani 0.14 1 d PU B 2 C57' C 0.7230(6) 0.451(4) 0.7872(10) 0.067(7) Uani 0.30 1 d PGDU B 2 C58' C 0.7323(5) 0.571(3) 0.7546(13) 0.085(7) Uani 0.30 1 d PGU B 2 C59' C 0.7260(5) 0.596(3) 0.6708(15) 0.096(8) Uani 0.25 1 d PGU B 2 H59' H 0.7322 0.6758 0.6490 0.115 Uiso 0.25 1 calc PR B 2 C60' C 0.7104(5) 0.500(3) 0.6195(10) 0.106(9) Uani 0.35 1 d PGU B 2 H60' H 0.7062 0.5164 0.5635 0.127 Uiso 0.35 1 calc PR B 2 C61' C 0.7011(6) 0.380(3) 0.6521(12) 0.104(10) Uani 0.25 1 d PGU B 2 H61' H 0.6907 0.3162 0.6178 0.125 Uiso 0.25 1 calc PR B 2 C62' C 0.7074(7) 0.356(3) 0.7359(14) 0.108(10) Uani 0.25 1 d PGU B 2 H62' H 0.7012 0.2753 0.7577 0.129 Uiso 0.25 1 calc PR B 2 C63 C 0.77034(10) 0.1890(6) 0.7491(4) 0.0545(15) Uani 1 1 d U . . C64 C 0.75581(14) 0.0674(8) 0.7494(4) 0.0775(19) Uani 1 1 d U . . H64 H 0.7563 0.0157 0.7972 0.093 Uiso 1 1 calc R . . C65 C 0.74016(14) 0.0248(8) 0.6743(5) 0.085(2) Uani 1 1 d U . . H65 H 0.7288 -0.0505 0.6724 0.103 Uiso 1 1 calc R . . C66 C 0.74193(13) 0.0943(9) 0.6062(4) 0.0746(19) Uani 1 1 d U . . C67 C 0.75568(15) 0.2127(10) 0.6046(4) 0.086(2) Uani 1 1 d U . . H67 H 0.7553 0.2612 0.5559 0.103 Uiso 1 1 calc R . . C68 C 0.77107(13) 0.2625(7) 0.6800(4) 0.0739(18) Uani 1 1 d U . . H68 H 0.7813 0.3429 0.6815 0.089 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 Br1 0.0935(5) 0.0974(6) 0.0878(5) -0.0382(5) 0.0251(4) -0.0178(5) Br2 0.0790(5) 0.1001(6) 0.1707(9) 0.0090(6) 0.0560(5) 0.0083(5) Br3 0.0628(4) 0.0780(5) 0.0740(4) 0.0066(4) 0.0105(3) -0.0159(4) S1 0.0689(11) 0.0570(10) 0.0837(12) -0.0024(10) -0.0125(9) 0.0074(9) S2 0.0974(15) 0.0903(14) 0.0592(11) 0.0074(10) -0.0094(9) -0.0137(12) S3 0.0581(9) 0.0638(10) 0.0523(9) -0.0037(8) 0.0131(7) 0.0046(8) S4 0.0462(8) 0.0933(13) 0.0600(9) -0.0155(9) 0.0147(7) -0.0012(10) N1 0.064(3) 0.063(3) 0.052(3) -0.002(2) 0.007(2) 0.013(3) N2 0.055(3) 0.072(4) 0.065(3) 0.000(3) -0.003(2) -0.002(3) N3 0.061(3) 0.077(4) 0.061(3) -0.011(3) -0.009(2) -0.003(3) N4 0.057(4) 0.066(4) 0.084(4) 0.019(3) 0.015(3) 0.008(3) N5 0.085(4) 0.068(3) 0.060(3) -0.005(3) 0.023(3) 0.000(3) N6 0.074(3) 0.072(4) 0.061(3) 0.002(3) 0.015(3) -0.011(3) N7 0.069(3) 0.069(3) 0.049(3) -0.014(3) 0.003(2) -0.014(3) N8 0.097(6) 0.081(6) 0.109(6) 0.020(4) -0.019(4) -0.001(5) N9 0.043(3) 0.054(3) 0.054(3) -0.006(2) 0.001(2) 0.000(2) N10 0.068(3) 0.053(3) 0.060(3) -0.005(3) -0.006(2) 0.000(3) N11 0.071(3) 0.061(3) 0.054(3) 0.006(2) 0.011(2) 0.012(3) N12 0.091(5) 0.080(5) 0.094(5) 0.012(4) 0.023(4) 0.016(4) N13 0.056(3) 0.062(3) 0.057(3) 0.005(2) 0.016(2) 0.002(2) N14 0.062(4) 0.089(4) 0.078(4) -0.038(3) 0.014(3) -0.002(3) N15 0.056(3) 0.087(4) 0.097(4) -0.027(3) 0.009(3) 0.012(3) N16 0.084(5) 0.155(8) 0.117(7) -0.048(6) 0.012(5) -0.025(5) O1 0.080(3) 0.095(4) 0.096(3) 0.033(3) 0.005(3) -0.004(3) O2 0.101(4) 0.076(3) 0.105(4) -0.031(3) -0.033(3) 0.009(3) O3 0.073(3) 0.088(4) 0.089(3) 0.001(3) 0.014(3) -0.005(3) O4 0.073(3) 0.095(4) 0.103(4) 0.005(3) 0.022(3) 0.023(3) O5 0.080(4) 0.134(5) 0.127(4) 0.023(4) -0.025(3) -0.019(4) O6 0.205(6) 0.117(5) 0.042(3) -0.007(3) 0.009(3) -0.026(4) O7 0.179(8) 0.085(5) 0.243(10) -0.066(6) 0.010(7) 0.009(5) O8 0.125(6) 0.117(6) 0.172(7) 0.050(5) -0.021(5) -0.035(5) O9 0.085(3) 0.070(3) 0.060(3) -0.008(2) 0.001(2) 0.011(2) O10 0.068(3) 0.088(3) 0.077(3) 0.012(2) 0.036(2) 0.003(3) O11 0.137(5) 0.096(4) 0.102(4) 0.027(3) 0.027(3) 0.012(4) O12 0.152(5) 0.127(5) 0.068(3) 0.024(4) -0.018(3) 0.004(5) O13 0.077(3) 0.143(5) 0.077(3) -0.039(3) 0.032(2) -0.063(3) O14 0.090(4) 0.157(5) 0.080(3) -0.012(3) 0.016(3) 0.059(4) O15 0.160(7) 0.249(10) 0.113(5) -0.073(7) -0.007(5) -0.067(8) O16 0.177(7) 0.246(10) 0.066(4) -0.018(5) -0.019(4) 0.007(7) C1 0.043(3) 0.065(4) 0.046(3) -0.004(3) -0.002(2) 0.009(3) C2 0.046(3) 0.069(4) 0.035(3) -0.001(3) -0.008(2) 0.002(3) C3 0.058(4) 0.063(4) 0.053(4) -0.001(3) -0.001(3) 0.002(3) C4 0.076(5) 0.062(4) 0.101(5) -0.004(4) -0.018(4) -0.001(4) C5 0.084(5) 0.068(5) 0.113(6) 0.010(5) -0.021(4) 0.006(4) C6 0.047(3) 0.078(4) 0.059(4) -0.004(3) 0.005(3) -0.001(3) C7 0.055(4) 0.182(9) 0.068(4) -0.030(5) 0.016(3) -0.004(5) C8 0.063(5) 0.198(10) 0.104(6) -0.047(7) 0.036(4) -0.021(6) C9 0.051(4) 0.106(6) 0.123(6) 0.014(5) 0.006(4) -0.014(4) C10 0.057(4) 0.073(5) 0.079(4) 0.003(4) -0.003(3) 0.004(3) C11 0.053(4) 0.064(4) 0.058(4) 0.012(3) -0.008(3) -0.010(3) C12 0.072(4) 0.052(4) 0.066(4) 0.000(3) -0.008(3) 0.015(3) C13 0.088(6) 0.053(4) 0.106(5) -0.016(4) 0.011(4) 0.012(4) C14 0.067(5) 0.059(4) 0.093(5) -0.005(4) 0.003(4) 0.021(4) C15 0.064(4) 0.059(4) 0.045(3) 0.007(3) 0.006(3) 0.007(3) C16 0.082(5) 0.049(4) 0.059(4) -0.009(3) -0.006(3) 0.011(3) C17 0.059(4) 0.052(4) 0.061(4) -0.006(3) -0.016(3) 0.021(3) C18 0.064(4) 0.069(4) 0.060(4) -0.006(3) 0.014(3) 0.003(3) C19 0.053(3) 0.071(4) 0.044(3) 0.005(3) 0.008(3) -0.004(3) C20 0.063(4) 0.067(4) 0.061(4) -0.008(3) 0.009(3) -0.004(3) C21 0.079(5) 0.112(6) 0.084(5) -0.026(5) 0.013(4) -0.035(5) C22 0.107(6) 0.097(6) 0.067(5) 0.012(4) -0.008(4) -0.019(5) C23 0.056(4) 0.056(4) 0.058(4) 0.001(3) 0.004(3) 0.001(3) C24 0.073(4) 0.073(5) 0.053(4) -0.009(3) -0.001(3) 0.003(4) C25 0.093(6) 0.087(6) 0.076(5) -0.024(4) 0.005(4) 0.012(5) C26 0.112(7) 0.055(5) 0.084(5) 0.000(4) -0.017(5) -0.006(5) C27 0.075(5) 0.073(5) 0.105(6) 0.009(4) 0.002(4) -0.008(4) C28 0.059(4) 0.060(4) 0.071(4) 0.008(3) 0.008(3) -0.002(3) C29 0.071(4) 0.080(5) 0.047(3) 0.015(3) 0.013(3) 0.017(4) C30 0.068(5) 0.078(5) 0.092(5) 0.016(4) 0.020(4) 0.010(4) C31 0.096(6) 0.062(5) 0.081(5) 0.012(4) 0.016(4) 0.023(4) C32 0.076(5) 0.056(4) 0.086(5) 0.018(4) -0.003(4) 0.007(4) C33 0.079(5) 0.075(5) 0.093(5) 0.013(4) 0.028(4) 0.003(4) C34 0.086(5) 0.069(5) 0.071(4) 0.001(4) 0.021(3) 0.011(4) C35 0.041(3) 0.053(3) 0.042(3) 0.000(3) 0.001(2) -0.008(3) C36 0.047(3) 0.057(4) 0.050(3) -0.003(3) 0.000(2) -0.001(3) C37 0.052(4) 0.061(4) 0.044(3) 0.007(3) 0.003(3) -0.003(3) C38 0.088(5) 0.110(7) 0.079(5) 0.013(4) 0.015(4) -0.020(5) C39 0.108(6) 0.096(6) 0.142(7) -0.012(6) 0.045(5) 0.040(5) C40 0.042(3) 0.059(4) 0.046(3) -0.002(3) 0.007(2) 0.001(3) C41 0.063(4) 0.073(4) 0.049(3) -0.011(3) 0.011(3) -0.011(3) C42 0.069(4) 0.096(6) 0.056(4) 0.000(4) 0.003(3) 0.000(4) C43 0.071(5) 0.120(7) 0.054(4) 0.011(4) 0.009(3) 0.006(5) C44 0.067(4) 0.101(5) 0.066(4) 0.022(4) 0.021(3) 0.004(4) C45 0.049(3) 0.077(4) 0.048(3) -0.016(3) 0.008(3) -0.006(3) C46 0.049(3) 0.052(4) 0.068(4) 0.008(3) 0.012(3) 0.017(3) C47 0.062(4) 0.039(3) 0.076(4) -0.002(3) 0.013(3) 0.005(3) C48 0.063(4) 0.057(4) 0.074(4) 0.008(3) 0.021(3) 0.008(3) C49 0.061(4) 0.062(4) 0.060(4) 0.007(3) 0.018(3) 0.016(4) C50 0.052(4) 0.082(5) 0.062(4) 0.003(4) -0.001(3) 0.005(3) C51 0.056(4) 0.066(4) 0.082(4) 0.007(4) 0.003(3) -0.015(3) C52 0.057(4) 0.055(4) 0.062(4) -0.008(3) 0.016(3) -0.006(3) C53 0.059(4) 0.062(4) 0.071(4) -0.010(3) 0.004(3) 0.003(3) C54 0.053(4) 0.075(4) 0.063(4) -0.021(3) 0.017(3) -0.018(4) C55 0.059(4) 0.126(6) 0.055(4) -0.020(4) 0.015(3) -0.010(4) C56 0.049(5) 0.206(11) 0.133(7) -0.069(8) 0.006(4) 0.010(6) Br4 0.0771(6) 0.1215(9) 0.1588(10) -0.0476(8) -0.0127(6) -0.0184(6) C57 0.053(8) 0.064(8) 0.075(7) -0.011(6) -0.001(5) 0.007(6) C58 0.076(9) 0.072(8) 0.099(8) 0.006(7) 0.005(7) -0.014(7) C59 0.108(10) 0.104(9) 0.125(10) 0.024(8) 0.033(8) 0.007(8) C60 0.071(9) 0.143(13) 0.076(8) 0.003(9) -0.022(7) -0.003(8) C61 0.102(9) 0.122(12) 0.078(7) 0.001(8) 0.012(7) 0.013(9) C62 0.064(7) 0.098(9) 0.091(7) -0.036(7) 0.005(6) 0.022(6) Br4' 0.128(5) 0.086(4) 0.124(5) 0.010(4) 0.037(4) -0.008(4) C57' 0.049(13) 0.091(16) 0.066(13) -0.021(12) 0.022(10) 0.015(13) C58' 0.083(16) 0.081(15) 0.094(14) 0.017(13) 0.030(12) -0.007(14) C59' 0.082(16) 0.116(16) 0.081(14) -0.013(14) 0.000(14) 0.008(14) C60' 0.101(17) 0.122(19) 0.090(14) -0.008(15) 0.010(13) 0.003(16) C61' 0.103(18) 0.13(2) 0.066(16) -0.015(16) -0.007(15) 0.009(18) C62' 0.065(17) 0.14(2) 0.099(18) -0.077(16) -0.035(16) 0.018(18) C63 0.049(3) 0.051(4) 0.068(4) -0.014(3) 0.022(3) -0.009(3) C64 0.091(5) 0.080(5) 0.059(4) -0.007(4) 0.012(4) -0.002(4) C65 0.084(5) 0.081(5) 0.091(6) -0.018(5) 0.019(4) -0.037(4) C66 0.066(4) 0.083(5) 0.066(5) -0.020(4) -0.005(4) 0.005(4) C67 0.107(6) 0.100(6) 0.047(4) 0.005(4) 0.011(4) 0.027(5) C68 0.084(5) 0.066(4) 0.077(5) 0.006(4) 0.027(4) -0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C11 1.852(6) . ? Br2 C28 1.869(7) . ? Br3 C45 1.910(6) . ? S1 O2 1.429(5) . ? S1 O1 1.455(5) . ? S1 N1 1.588(5) . ? S1 C12 1.793(7) . ? S2 O5 1.415(6) . ? S2 O6 1.431(6) . ? S2 N5 1.616(6) . ? S2 C29 1.775(7) . ? S3 O9 1.405(4) . ? S3 O10 1.430(4) . ? S3 N9 1.610(5) . ? S3 C46 1.757(6) . ? S4 O14 1.405(6) . ? S4 O13 1.432(5) . ? S4 N13 1.585(5) . ? S4 C63 1.773(6) . ? N1 C1 1.447(7) . ? N1 H1A 0.8600 . ? N2 N3 1.413(7) . ? N2 C5 1.428(9) . ? N2 C2 1.447(7) . ? N3 C3 1.295(8) . ? N4 O4 1.201(7) . ? N4 O3 1.264(7) . ? N4 C15 1.430(8) . ? N5 C18 1.440(7) . ? N5 H5 0.8600 . ? N6 C20 1.264(7) . ? N6 N7 1.402(7) . ? N7 C22 1.464(8) . ? N7 C19 1.465(7) . ? N8 O7 1.172(10) . ? N8 O8 1.229(10) . ? N8 C32 1.515(10) . ? N9 C35 1.454(7) . ? N9 H9 0.8600 . ? N10 C37 1.272(7) . ? N10 N11 1.418(7) . ? N11 C36 1.446(8) . ? N11 C39 1.458(8) . ? N12 O12 1.207(8) . ? N12 O11 1.222(8) . ? N12 C49 1.485(9) . ? N13 C52 1.448(8) . ? N13 H13 0.8600 . ? N14 C54 1.280(7) . ? N14 N15 1.446(8) . ? N15 C53 1.468(8) . ? N15 C56 1.468(9) . ? N16 O15 1.197(11) . ? N16 O16 1.229(11) . ? N16 C66 1.457(11) . ? C1 C3 1.516(8) . ? C1 C2 1.543(9) . ? C1 H1 0.9800 . ? C2 C6 1.497(8) . ? C2 H2 0.9800 . ? C3 C4 1.461(9) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.397(9) . ? C6 C11 1.430(8) . ? C7 C8 1.367(10) . ? C7 H7 0.9300 . ? C8 C9 1.380(11) . ? C8 H8A 0.9300 . ? C9 C10 1.357(10) . ? C9 H9A 0.9300 . ? C10 C11 1.363(8) . ? C10 H10 0.9300 . ? C12 C17 1.343(8) . ? C12 C13 1.381(9) . ? C13 C14 1.363(9) . ? C13 H13A 0.9300 . ? C14 C15 1.344(9) . ? C14 H14 0.9300 . ? C15 C16 1.398(8) . ? C16 C17 1.360(8) . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.504(8) . ? C18 C20 1.551(9) . ? C18 H18 0.9800 . ? C19 C23 1.515(8) . ? C19 H19 0.9800 . ? C20 C21 1.469(9) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.398(9) . ? C23 C28 1.400(8) . ? C24 C25 1.401(10) . ? C24 H24 0.9300 . ? C25 C26 1.360(11) . ? C25 H25 0.9300 . ? C26 C27 1.362(11) . ? C26 H26 0.9300 . ? C27 C28 1.393(10) . ? C27 H27 0.9300 . ? C29 C34 1.319(8) . ? C29 C30 1.341(9) . ? C30 C31 1.381(10) . ? C30 H30 0.9300 . ? C31 C32 1.318(10) . ? C31 H31 0.9300 . ? C32 C33 1.348(10) . ? C33 C34 1.369(10) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C37 1.491(8) . ? C35 C36 1.528(7) . ? C35 H35 0.9800 . ? C36 C40 1.502(7) . ? C36 H36 0.9800 . ? C37 C38 1.445(8) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 C45 1.358(8) . ? C40 C41 1.392(8) . ? C41 C42 1.396(8) . ? C41 H41 0.9300 . ? C42 C43 1.385(10) . ? C42 H42 0.9300 . ? C43 C44 1.407(10) . ? C43 H43 0.9300 . ? C44 C45 1.393(8) . ? C44 H44 0.9300 . ? C46 C47 1.396(8) . ? C46 C51 1.417(8) . ? C47 C48 1.404(8) . ? C47 H47 0.9300 . ? C48 C49 1.317(8) . ? C48 H48 0.9300 . ? C49 C50 1.374(9) . ? C50 C51 1.359(8) . ? C50 H50 0.9300 . ? C51 H51 0.9300 . ? C52 C54 1.506(8) . ? C52 C53 1.513(8) . ? C52 H52 0.9800 . ? C53 C57' 1.476(15) . ? C53 C57 1.589(9) . ? C53 H53 0.9800 . ? C53 H53' 0.9614 . ? C54 C55 1.485(9) . ? C55 H55A 0.9600 . ? C55 H55B 0.9600 . ? C55 H55C 0.9600 . ? C56 H56A 0.9600 . ? C56 H56B 0.9600 . ? C56 H56C 0.9600 . ? Br4 C62 1.916(8) . ? C57 C58 1.3900 . ? C57 C62 1.3900 . ? C58 C59 1.3900 . ? C58 H58 0.9300 . ? C59 C60 1.3900 . ? C59 H59 0.9300 . ? C60 C61 1.3900 . ? C60 H60 0.9300 . ? C61 C62 1.3900 . ? C61 H61 0.9300 . ? Br4' C58' 1.63(2) . ? C57' C58' 1.3900 . ? C57' C62' 1.3900 . ? C58' C59' 1.3900 . ? C59' C60' 1.3900 . ? C59' H59' 0.9300 . ? C60' C61' 1.3900 . ? C60' H60' 0.9300 . ? C61' C62' 1.3900 . ? C61' H61' 0.9300 . ? C62' H62' 0.9300 . ? C63 C68 1.354(8) . ? C63 C64 1.383(9) . ? C64 C65 1.412(9) . ? C64 H64 0.9300 . ? C65 C66 1.334(10) . ? C65 H65 0.9300 . ? C66 C67 1.338(11) . ? C67 C68 1.431(10) . ? C67 H67 0.9300 . ? C68 H68 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 121.1(4) . . ? O2 S1 N1 109.8(3) . . ? O1 S1 N1 105.5(3) . . ? O2 S1 C12 106.0(3) . . ? O1 S1 C12 108.1(3) . . ? N1 S1 C12 105.4(3) . . ? O5 S2 O6 120.0(4) . . ? O5 S2 N5 107.7(3) . . ? O6 S2 N5 107.1(3) . . ? O5 S2 C29 107.4(4) . . ? O6 S2 C29 108.6(3) . . ? N5 S2 C29 105.2(3) . . ? O9 S3 O10 120.7(3) . . ? O9 S3 N9 106.0(2) . . ? O10 S3 N9 108.0(3) . . ? O9 S3 C46 107.6(3) . . ? O10 S3 C46 105.9(3) . . ? N9 S3 C46 108.1(2) . . ? O14 S4 O13 120.6(4) . . ? O14 S4 N13 106.5(3) . . ? O13 S4 N13 108.4(3) . . ? O14 S4 C63 106.8(3) . . ? O13 S4 C63 105.2(3) . . ? N13 S4 C63 108.9(2) . . ? C1 N1 S1 124.6(4) . . ? C1 N1 H1A 117.7 . . ? S1 N1 H1A 117.7 . . ? N3 N2 C5 110.3(5) . . ? N3 N2 C2 108.2(5) . . ? C5 N2 C2 114.3(5) . . ? C3 N3 N2 109.4(5) . . ? O4 N4 O3 123.6(6) . . ? O4 N4 C15 118.7(7) . . ? O3 N4 C15 117.7(6) . . ? C18 N5 S2 121.4(4) . . ? C18 N5 H5 119.3 . . ? S2 N5 H5 119.3 . . ? C20 N6 N7 111.0(5) . . ? N6 N7 C22 110.5(5) . . ? N6 N7 C19 108.0(4) . . ? C22 N7 C19 115.7(5) . . ? O7 N8 O8 126.6(10) . . ? O7 N8 C32 117.7(9) . . ? O8 N8 C32 115.7(9) . . ? C35 N9 S3 123.2(4) . . ? C35 N9 H9 118.4 . . ? S3 N9 H9 118.4 . . ? C37 N10 N11 108.4(5) . . ? N10 N11 C36 108.0(4) . . ? N10 N11 C39 110.2(5) . . ? C36 N11 C39 113.6(6) . . ? O12 N12 O11 122.9(7) . . ? O12 N12 C49 119.9(7) . . ? O11 N12 C49 117.2(7) . . ? C52 N13 S4 123.2(4) . . ? C52 N13 H13 118.4 . . ? S4 N13 H13 118.4 . . ? C54 N14 N15 109.0(5) . . ? N14 N15 C53 106.0(5) . . ? N14 N15 C56 108.5(6) . . ? C53 N15 C56 114.2(6) . . ? O15 N16 O16 124.4(10) . . ? O15 N16 C66 117.1(10) . . ? O16 N16 C66 118.4(10) . . ? N1 C1 C3 114.3(5) . . ? N1 C1 C2 113.7(5) . . ? C3 C1 C2 100.3(5) . . ? N1 C1 H1 109.4 . . ? C3 C1 H1 109.4 . . ? C2 C1 H1 109.4 . . ? N2 C2 C6 112.7(5) . . ? N2 C2 C1 102.7(4) . . ? C6 C2 C1 115.7(5) . . ? N2 C2 H2 108.5 . . ? C6 C2 H2 108.5 . . ? C1 C2 H2 108.5 . . ? N3 C3 C4 123.7(5) . . ? N3 C3 C1 112.0(5) . . ? C4 C3 C1 124.2(6) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 117.0(6) . . ? C7 C6 C2 119.2(6) . . ? C11 C6 C2 123.8(5) . . ? C8 C7 C6 120.8(7) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 121.0(7) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? C10 C9 C8 119.4(7) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? C9 C10 C11 121.5(7) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C6 120.3(6) . . ? C10 C11 Br1 118.4(5) . . ? C6 C11 Br1 121.3(4) . . ? C17 C12 C13 120.9(6) . . ? C17 C12 S1 120.9(5) . . ? C13 C12 S1 118.2(5) . . ? C14 C13 C12 119.4(7) . . ? C14 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C15 C14 C13 120.2(6) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.2(6) . . ? C14 C15 N4 119.3(6) . . ? C16 C15 N4 120.5(6) . . ? C17 C16 C15 119.3(6) . . ? C17 C16 H16A 120.3 . . ? C15 C16 H16A 120.3 . . ? C12 C17 C16 120.0(6) . . ? C12 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? N5 C18 C19 117.0(5) . . ? N5 C18 C20 113.0(5) . . ? C19 C18 C20 100.7(5) . . ? N5 C18 H18 108.6 . . ? C19 C18 H18 108.6 . . ? C20 C18 H18 108.6 . . ? N7 C19 C18 102.0(5) . . ? N7 C19 C23 112.0(5) . . ? C18 C19 C23 116.9(5) . . ? N7 C19 H19 108.5 . . ? C18 C19 H19 108.5 . . ? C23 C19 H19 108.5 . . ? N6 C20 C21 126.0(6) . . ? N6 C20 C18 110.3(5) . . ? C21 C20 C18 123.4(6) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N7 C22 H22A 109.5 . . ? N7 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N7 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 119.2(6) . . ? C24 C23 C19 118.4(6) . . ? C28 C23 C19 122.3(6) . . ? C23 C24 C25 119.0(7) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C26 C25 C24 120.7(7) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C27 120.9(7) . . ? C25 C26 H26 119.5 . . ? C27 C26 H26 119.5 . . ? C26 C27 C28 120.1(7) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C23 119.9(7) . . ? C27 C28 Br2 117.7(6) . . ? C23 C28 Br2 122.4(5) . . ? C34 C29 C30 121.5(7) . . ? C34 C29 S2 118.9(6) . . ? C30 C29 S2 119.6(6) . . ? C29 C30 C31 119.3(7) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C32 C31 C30 117.8(7) . . ? C32 C31 H31 121.1 . . ? C30 C31 H31 121.1 . . ? C31 C32 C33 123.8(7) . . ? C31 C32 N8 117.1(8) . . ? C33 C32 N8 119.0(8) . . ? C32 C33 C34 117.1(7) . . ? C32 C33 H33 121.5 . . ? C34 C33 H33 121.5 . . ? C29 C34 C33 120.4(7) . . ? C29 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? N9 C35 C37 116.5(4) . . ? N9 C35 C36 115.5(4) . . ? C37 C35 C36 100.4(5) . . ? N9 C35 H35 108.0 . . ? C37 C35 H35 108.0 . . ? C36 C35 H35 108.0 . . ? N11 C36 C40 112.9(5) . . ? N11 C36 C35 101.6(4) . . ? C40 C36 C35 115.3(4) . . ? N11 C36 H36 108.9 . . ? C40 C36 H36 108.9 . . ? C35 C36 H36 108.9 . . ? N10 C37 C38 122.8(6) . . ? N10 C37 C35 113.0(5) . . ? C38 C37 C35 123.8(6) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N11 C39 H39A 109.5 . . ? N11 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N11 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C45 C40 C41 117.6(5) . . ? C45 C40 C36 124.9(5) . . ? C41 C40 C36 117.5(5) . . ? C40 C41 C42 121.1(6) . . ? C40 C41 H41 119.4 . . ? C42 C41 H41 119.4 . . ? C43 C42 C41 120.3(6) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C42 C43 C44 119.0(6) . . ? C42 C43 H43 120.5 . . ? C44 C43 H43 120.5 . . ? C45 C44 C43 118.5(7) . . ? C45 C44 H44 120.7 . . ? C43 C44 H44 120.7 . . ? C40 C45 C44 123.4(6) . . ? C40 C45 Br3 121.2(4) . . ? C44 C45 Br3 115.4(5) . . ? C47 C46 C51 120.4(6) . . ? C47 C46 S3 119.4(5) . . ? C51 C46 S3 120.2(5) . . ? C46 C47 C48 117.9(6) . . ? C46 C47 H47 121.1 . . ? C48 C47 H47 121.1 . . ? C49 C48 C47 119.7(6) . . ? C49 C48 H48 120.2 . . ? C47 C48 H48 120.2 . . ? C48 C49 C50 124.2(6) . . ? C48 C49 N12 120.5(7) . . ? C50 C49 N12 115.3(6) . . ? C51 C50 C49 118.6(6) . . ? C51 C50 H50 120.7 . . ? C49 C50 H50 120.7 . . ? C50 C51 C46 119.2(6) . . ? C50 C51 H51 120.4 . . ? C46 C51 H51 120.4 . . ? N13 C52 C54 114.3(5) . . ? N13 C52 C53 116.1(5) . . ? C54 C52 C53 100.4(5) . . ? N13 C52 H52 108.5 . . ? C54 C52 H52 108.5 . . ? C53 C52 H52 108.5 . . ? N15 C53 C57' 111.2(16) . . ? N15 C53 C52 103.1(5) . . ? C57' C53 C52 125.4(13) . . ? N15 C53 C57 110.2(7) . . ? C57' C53 C57 16.1(13) . . ? C52 C53 C57 111.8(6) . . ? N15 C53 H53 110.5 . . ? C57' C53 H53 95.8 . . ? C52 C53 H53 110.5 . . ? C57 C53 H53 110.5 . . ? N15 C53 H53' 120.3 . . ? C57' C53 H53' 95.0 . . ? C52 C53 H53' 102.9 . . ? C57 C53 H53' 108.2 . . ? H53 C53 H53' 10.5 . . ? N14 C54 C55 123.3(5) . . ? N14 C54 C52 112.9(5) . . ? C55 C54 C52 123.8(6) . . ? C54 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C54 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? N15 C56 H56A 109.5 . . ? N15 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? N15 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C58 C57 C62 120.0 . . ? C58 C57 C53 121.7(7) . . ? C62 C57 C53 118.3(7) . . ? C57 C58 C59 120.0 . . ? C57 C58 H58 120.0 . . ? C59 C58 H58 120.0 . . ? C58 C59 C60 120.0 . . ? C58 C59 H59 120.0 . . ? C60 C59 H59 120.0 . . ? C61 C60 C59 120.0 . . ? C61 C60 H60 120.0 . . ? C59 C60 H60 120.0 . . ? C62 C61 C60 120.0 . . ? C62 C61 H61 120.0 . . ? C60 C61 H61 120.0 . . ? C61 C62 C57 120.0 . . ? C61 C62 Br4 116.6(6) . . ? C57 C62 Br4 123.4(6) . . ? C58' C57' C62' 120.0 . . ? C58' C57' C53 115.3(18) . . ? C62' C57' C53 124.2(19) . . ? C57' C58' C59' 120.0 . . ? C57' C58' Br4' 125.5(17) . . ? C59' C58' Br4' 114.1(17) . . ? C58' C59' C60' 120.0 . . ? C58' C59' H59' 120.0 . . ? C60' C59' H59' 120.0 . . ? C61' C60' C59' 120.0 . . ? C61' C60' H60' 120.0 . . ? C59' C60' H60' 120.0 . . ? C60' C61' C62' 120.0 . . ? C60' C61' H61' 120.0 . . ? C62' C61' H61' 120.0 . . ? C61' C62' C57' 120.0 . . ? C61' C62' H62' 120.0 . . ? C57' C62' H62' 120.0 . . ? C68 C63 C64 122.9(6) . . ? C68 C63 S4 120.7(5) . . ? C64 C63 S4 116.2(5) . . ? C63 C64 C65 117.3(7) . . ? C63 C64 H64 121.4 . . ? C65 C64 H64 121.4 . . ? C66 C65 C64 119.0(7) . . ? C66 C65 H65 120.5 . . ? C64 C65 H65 120.5 . . ? C65 C66 C67 124.3(6) . . ? C65 C66 N16 118.5(8) . . ? C67 C66 N16 117.1(8) . . ? C66 C67 C68 118.1(7) . . ? C66 C67 H67 121.0 . . ? C68 C67 H67 121.0 . . ? C63 C68 C67 118.0(6) . . ? C63 C68 H68 121.0 . . ? C67 C68 H68 121.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N1 C1 41.4(6) . . . . ? O1 S1 N1 C1 173.4(5) . . . . ? C12 S1 N1 C1 -72.4(5) . . . . ? C5 N2 N3 C3 146.7(6) . . . . ? C2 N2 N3 C3 21.0(7) . . . . ? O5 S2 N5 C18 40.7(6) . . . . ? O6 S2 N5 C18 170.9(5) . . . . ? C29 S2 N5 C18 -73.7(5) . . . . ? C20 N6 N7 C22 145.7(6) . . . . ? C20 N6 N7 C19 18.2(7) . . . . ? O9 S3 N9 C35 172.2(4) . . . . ? O10 S3 N9 C35 41.6(5) . . . . ? C46 S3 N9 C35 -72.6(5) . . . . ? C37 N10 N11 C36 20.6(6) . . . . ? C37 N10 N11 C39 145.3(6) . . . . ? O14 S4 N13 C52 159.1(5) . . . . ? O13 S4 N13 C52 27.9(5) . . . . ? C63 S4 N13 C52 -86.1(5) . . . . ? C54 N14 N15 C53 19.7(7) . . . . ? C54 N14 N15 C56 142.7(7) . . . . ? S1 N1 C1 C3 -106.7(5) . . . . ? S1 N1 C1 C2 138.9(5) . . . . ? N3 N2 C2 C6 -152.7(5) . . . . ? C5 N2 C2 C6 84.0(7) . . . . ? N3 N2 C2 C1 -27.5(6) . . . . ? C5 N2 C2 C1 -150.8(6) . . . . ? N1 C1 C2 N2 145.5(4) . . . . ? C3 C1 C2 N2 23.0(6) . . . . ? N1 C1 C2 C6 -91.3(6) . . . . ? C3 C1 C2 C6 146.2(5) . . . . ? N2 N3 C3 C4 173.0(6) . . . . ? N2 N3 C3 C1 -4.5(7) . . . . ? N1 C1 C3 N3 -134.3(6) . . . . ? C2 C1 C3 N3 -12.2(7) . . . . ? N1 C1 C3 C4 48.2(8) . . . . ? C2 C1 C3 C4 170.3(6) . . . . ? N2 C2 C6 C7 58.7(9) . . . . ? C1 C2 C6 C7 -59.1(8) . . . . ? N2 C2 C6 C11 -122.9(6) . . . . ? C1 C2 C6 C11 119.4(6) . . . . ? C11 C6 C7 C8 -1.9(13) . . . . ? C2 C6 C7 C8 176.7(8) . . . . ? C6 C7 C8 C9 0.0(16) . . . . ? C7 C8 C9 C10 0.9(15) . . . . ? C8 C9 C10 C11 0.1(12) . . . . ? C9 C10 C11 C6 -2.1(10) . . . . ? C9 C10 C11 Br1 178.5(6) . . . . ? C7 C6 C11 C10 2.9(10) . . . . ? C2 C6 C11 C10 -175.6(6) . . . . ? C7 C6 C11 Br1 -177.7(6) . . . . ? C2 C6 C11 Br1 3.8(8) . . . . ? O2 S1 C12 C17 -151.1(6) . . . . ? O1 S1 C12 C17 77.7(6) . . . . ? N1 S1 C12 C17 -34.7(6) . . . . ? O2 S1 C12 C13 30.8(7) . . . . ? O1 S1 C12 C13 -100.4(6) . . . . ? N1 S1 C12 C13 147.3(6) . . . . ? C17 C12 C13 C14 -0.2(11) . . . . ? S1 C12 C13 C14 177.9(6) . . . . ? C12 C13 C14 C15 0.1(11) . . . . ? C13 C14 C15 C16 -0.2(10) . . . . ? C13 C14 C15 N4 -179.4(6) . . . . ? O4 N4 C15 C14 -14.0(8) . . . . ? O3 N4 C15 C14 166.0(6) . . . . ? O4 N4 C15 C16 166.8(5) . . . . ? O3 N4 C15 C16 -13.2(8) . . . . ? C14 C15 C16 C17 0.3(9) . . . . ? N4 C15 C16 C17 179.5(5) . . . . ? C13 C12 C17 C16 0.3(10) . . . . ? S1 C12 C17 C16 -177.6(5) . . . . ? C15 C16 C17 C12 -0.4(9) . . . . ? S2 N5 C18 C19 125.3(5) . . . . ? S2 N5 C18 C20 -118.4(5) . . . . ? N6 N7 C19 C18 -27.8(6) . . . . ? C22 N7 C19 C18 -152.2(6) . . . . ? N6 N7 C19 C23 -153.5(5) . . . . ? C22 N7 C19 C23 82.0(7) . . . . ? N5 C18 C19 N7 148.5(5) . . . . ? C20 C18 C19 N7 25.6(6) . . . . ? N5 C18 C19 C23 -89.0(7) . . . . ? C20 C18 C19 C23 148.1(5) . . . . ? N7 N6 C20 C21 173.0(6) . . . . ? N7 N6 C20 C18 -0.1(7) . . . . ? N5 C18 C20 N6 -142.6(6) . . . . ? C19 C18 C20 N6 -17.0(6) . . . . ? N5 C18 C20 C21 44.0(9) . . . . ? C19 C18 C20 C21 169.7(6) . . . . ? N7 C19 C23 C24 48.1(7) . . . . ? C18 C19 C23 C24 -69.1(7) . . . . ? N7 C19 C23 C28 -133.1(6) . . . . ? C18 C19 C23 C28 109.7(7) . . . . ? C28 C23 C24 C25 0.8(9) . . . . ? C19 C23 C24 C25 179.5(5) . . . . ? C23 C24 C25 C26 3.1(10) . . . . ? C24 C25 C26 C27 -4.4(11) . . . . ? C25 C26 C27 C28 1.6(11) . . . . ? C26 C27 C28 C23 2.4(10) . . . . ? C26 C27 C28 Br2 -178.9(5) . . . . ? C24 C23 C28 C27 -3.5(9) . . . . ? C19 C23 C28 C27 177.8(6) . . . . ? C24 C23 C28 Br2 177.9(5) . . . . ? C19 C23 C28 Br2 -0.8(8) . . . . ? O5 S2 C29 C34 161.7(5) . . . . ? O6 S2 C29 C34 30.5(6) . . . . ? N5 S2 C29 C34 -83.9(5) . . . . ? O5 S2 C29 C30 -21.0(6) . . . . ? O6 S2 C29 C30 -152.1(6) . . . . ? N5 S2 C29 C30 93.5(6) . . . . ? C34 C29 C30 C31 1.4(10) . . . . ? S2 C29 C30 C31 -175.9(5) . . . . ? C29 C30 C31 C32 -3.2(10) . . . . ? C30 C31 C32 C33 2.0(11) . . . . ? C30 C31 C32 N8 -175.1(6) . . . . ? O7 N8 C32 C31 -4.3(11) . . . . ? O8 N8 C32 C31 175.2(7) . . . . ? O7 N8 C32 C33 178.5(8) . . . . ? O8 N8 C32 C33 -2.0(10) . . . . ? C31 C32 C33 C34 1.1(11) . . . . ? N8 C32 C33 C34 178.1(6) . . . . ? C30 C29 C34 C33 1.8(10) . . . . ? S2 C29 C34 C33 179.1(5) . . . . ? C32 C33 C34 C29 -3.0(10) . . . . ? S3 N9 C35 C37 -118.1(5) . . . . ? S3 N9 C35 C36 124.4(4) . . . . ? N10 N11 C36 C40 -153.0(4) . . . . ? C39 N11 C36 C40 84.5(6) . . . . ? N10 N11 C36 C35 -28.9(5) . . . . ? C39 N11 C36 C35 -151.4(5) . . . . ? N9 C35 C36 N11 151.8(4) . . . . ? C37 C35 C36 N11 25.5(5) . . . . ? N9 C35 C36 C40 -85.8(6) . . . . ? C37 C35 C36 C40 148.0(5) . . . . ? N11 N10 C37 C38 170.6(6) . . . . ? N11 N10 C37 C35 -2.2(6) . . . . ? N9 C35 C37 N10 -140.9(5) . . . . ? C36 C35 C37 N10 -15.4(6) . . . . ? N9 C35 C37 C38 46.3(7) . . . . ? C36 C35 C37 C38 171.9(6) . . . . ? N11 C36 C40 C45 -141.3(6) . . . . ? C35 C36 C40 C45 102.6(6) . . . . ? N11 C36 C40 C41 38.4(7) . . . . ? C35 C36 C40 C41 -77.7(7) . . . . ? C45 C40 C41 C42 -0.9(9) . . . . ? C36 C40 C41 C42 179.4(5) . . . . ? C40 C41 C42 C43 1.8(10) . . . . ? C41 C42 C43 C44 -2.5(10) . . . . ? C42 C43 C44 C45 2.5(10) . . . . ? C41 C40 C45 C44 0.8(9) . . . . ? C36 C40 C45 C44 -179.5(6) . . . . ? C41 C40 C45 Br3 179.7(4) . . . . ? C36 C40 C45 Br3 -0.6(8) . . . . ? C43 C44 C45 C40 -1.7(9) . . . . ? C43 C44 C45 Br3 179.4(5) . . . . ? O9 S3 C46 C47 22.1(5) . . . . ? O10 S3 C46 C47 152.5(4) . . . . ? N9 S3 C46 C47 -92.0(5) . . . . ? O9 S3 C46 C51 -159.8(5) . . . . ? O10 S3 C46 C51 -29.5(5) . . . . ? N9 S3 C46 C51 86.1(5) . . . . ? C51 C46 C47 C48 1.7(8) . . . . ? S3 C46 C47 C48 179.7(4) . . . . ? C46 C47 C48 C49 0.3(8) . . . . ? C47 C48 C49 C50 -0.9(9) . . . . ? C47 C48 C49 N12 177.9(5) . . . . ? O12 N12 C49 C48 -178.9(7) . . . . ? O11 N12 C49 C48 -1.1(9) . . . . ? O12 N12 C49 C50 0.0(9) . . . . ? O11 N12 C49 C50 177.8(6) . . . . ? C48 C49 C50 C51 -0.5(10) . . . . ? N12 C49 C50 C51 -179.4(6) . . . . ? C49 C50 C51 C46 2.5(9) . . . . ? C47 C46 C51 C50 -3.1(9) . . . . ? S3 C46 C51 C50 178.9(5) . . . . ? S4 N13 C52 C54 -141.4(4) . . . . ? S4 N13 C52 C53 102.5(5) . . . . ? N14 N15 C53 C57' -165.6(13) . . . . ? C56 N15 C53 C57' 74.9(14) . . . . ? N14 N15 C53 C52 -28.9(6) . . . . ? C56 N15 C53 C52 -148.3(7) . . . . ? N14 N15 C53 C57 -148.4(6) . . . . ? C56 N15 C53 C57 92.2(8) . . . . ? N13 C52 C53 N15 150.2(5) . . . . ? C54 C52 C53 N15 26.5(6) . . . . ? N13 C52 C53 C57' -81.4(18) . . . . ? C54 C52 C53 C57' 154.9(18) . . . . ? N13 C52 C53 C57 -91.4(8) . . . . ? C54 C52 C53 C57 144.8(7) . . . . ? N15 N14 C54 C55 175.3(6) . . . . ? N15 N14 C54 C52 -1.4(7) . . . . ? N13 C52 C54 N14 -141.4(5) . . . . ? C53 C52 C54 N14 -16.4(7) . . . . ? N13 C52 C54 C55 41.9(8) . . . . ? C53 C52 C54 C55 166.9(7) . . . . ? N15 C53 C57 C58 67.9(9) . . . . ? C57' C53 C57 C58 165(8) . . . . ? C52 C53 C57 C58 -46.2(10) . . . . ? N15 C53 C57 C62 -112.3(8) . . . . ? C57' C53 C57 C62 -16(7) . . . . ? C52 C53 C57 C62 133.6(7) . . . . ? C62 C57 C58 C59 0.0 . . . . ? C53 C57 C58 C59 179.8(11) . . . . ? C57 C58 C59 C60 0.0 . . . . ? C58 C59 C60 C61 0.0 . . . . ? C59 C60 C61 C62 0.0 . . . . ? C60 C61 C62 C57 0.0 . . . . ? C60 C61 C62 Br4 -179.4(8) . . . . ? C58 C57 C62 C61 0.0 . . . . ? C53 C57 C62 C61 -179.8(11) . . . . ? C58 C57 C62 Br4 179.4(9) . . . . ? C53 C57 C62 Br4 -0.4(9) . . . . ? N15 C53 C57' C58' 69(2) . . . . ? C52 C53 C57' C58' -56(3) . . . . ? C57 C53 C57' C58' -20(6) . . . . ? N15 C53 C57' C62' -119.2(17) . . . . ? C52 C53 C57' C62' 115.7(16) . . . . ? C57 C53 C57' C62' 151(8) . . . . ? C62' C57' C58' C59' 0.0 . . . . ? C53 C57' C58' C59' 172(3) . . . . ? C62' C57' C58' Br4' 173(3) . . . . ? C53 C57' C58' Br4' -15(3) . . . . ? C57' C58' C59' C60' 0.0 . . . . ? Br4' C58' C59' C60' -173(2) . . . . ? C58' C59' C60' C61' 0.0 . . . . ? C59' C60' C61' C62' 0.0 . . . . ? C60' C61' C62' C57' 0.0 . . . . ? C58' C57' C62' C61' 0.0 . . . . ? C53 C57' C62' C61' -171(3) . . . . ? O14 S4 C63 C68 -123.5(5) . . . . ? O13 S4 C63 C68 5.8(6) . . . . ? N13 S4 C63 C68 121.9(5) . . . . ? O14 S4 C63 C64 52.0(5) . . . . ? O13 S4 C63 C64 -178.7(5) . . . . ? N13 S4 C63 C64 -62.6(5) . . . . ? C68 C63 C64 C65 -3.6(10) . . . . ? S4 C63 C64 C65 -179.0(5) . . . . ? C63 C64 C65 C66 6.4(11) . . . . ? C64 C65 C66 C67 -7.5(12) . . . . ? C64 C65 C66 N16 175.6(7) . . . . ? O15 N16 C66 C65 -4.0(13) . . . . ? O16 N16 C66 C65 178.9(9) . . . . ? O15 N16 C66 C67 178.9(9) . . . . ? O16 N16 C66 C67 1.7(12) . . . . ? C65 C66 C67 C68 5.0(12) . . . . ? N16 C66 C67 C68 -178.0(7) . . . . ? C64 C63 C68 C67 1.2(9) . . . . ? S4 C63 C68 C67 176.5(5) . . . . ? C66 C67 C68 C63 -1.7(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N13 H13 N14 0.86 2.10 2.946(7) 167.9 4_647 N9 H9 N3 0.86 2.28 3.129(7) 170.7 2_657 N5 H5 O7 0.86 2.45 3.124(10) 135.8 1_565 N1 H1A N6 0.86 2.11 2.968(7) 172.6 2_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.648 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.057