# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2 _database_code_depnum_ccdc_archive 'CCDC 900766' #TrackingRef '13856_web_deposit_cif_file_0_RobertMcDonald_1347316575.dlcacie.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'marinopyrrole B' _chemical_melting_point ? _chemical_formula_moiety 'C22 H11 Br Cl4 N2 O4, C7 H8' _chemical_formula_sum 'C29 H19 Br Cl4 N2 O4' _chemical_formula_weight 681.17 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7643(5) _cell_length_b 24.1282(15) _cell_length_c 15.4992(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.4921(8) _cell_angle_gamma 90.00 _cell_volume 2871.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6748 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 24.00 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 1.842 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.4838 _exptl_absorpt_correction_T_max 0.7722 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22995 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.47 _reflns_number_total 5919 _reflns_number_gt 4803 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0372P)^2^+1.3072P] 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 5919 _refine_ls_number_parameters 374 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br -0.11221(3) 0.277372(10) 0.206506(16) 0.03845(8) Uani 1 1 d . . . Cl1 Cl 0.03519(8) 0.30685(2) 0.42639(4) 0.03573(14) Uani 1 1 d . . . Cl2 Cl 0.15692(7) 0.18569(2) 0.53253(3) 0.03259(13) Uani 1 1 d . . . Cl3 Cl -0.22813(7) 0.05505(2) 0.33787(4) 0.03555(14) Uani 1 1 d . . . Cl4 Cl 0.00694(7) -0.06206(2) 0.40155(4) 0.03281(13) Uani 1 1 d . . . O1 O 0.1116(2) 0.10841(7) 0.19738(11) 0.0375(4) Uani 1 1 d . . . O2 O -0.0300(3) 0.08772(7) 0.03748(12) 0.0410(4) Uani 1 1 d . . . H2O H 0.046(4) 0.0855(13) 0.081(2) 0.055(10) Uiso 1 1 d . . . O3 O 0.5369(2) 0.07053(6) 0.50732(10) 0.0333(4) Uani 1 1 d . . . O4 O 0.6886(2) 0.16399(8) 0.55831(13) 0.0430(5) Uani 1 1 d . . . H4O H 0.675(4) 0.1352(13) 0.561(2) 0.054(10) Uiso 1 1 d . . . N1 N 0.0640(2) 0.15120(7) 0.36700(11) 0.0231(4) Uani 1 1 d . . . N2 N 0.2476(2) 0.01773(7) 0.42803(12) 0.0260(4) Uani 1 1 d . . . H2N H 0.323(3) -0.0038(11) 0.4501(16) 0.037(7) Uiso 1 1 d . . . C1 C -0.0092(3) 0.17138(9) 0.28543(14) 0.0253(4) Uani 1 1 d . . . C2 C -0.0303(3) 0.22757(9) 0.29487(14) 0.0265(5) Uani 1 1 d . . . C3 C 0.0294(3) 0.24194(9) 0.38196(15) 0.0273(5) Uani 1 1 d . . . C4 C 0.0835(3) 0.19439(9) 0.42491(13) 0.0242(4) Uani 1 1 d . . . C5 C 0.2706(3) 0.07375(8) 0.41762(14) 0.0239(4) Uani 1 1 d . . . C6 C 0.1086(3) 0.09521(8) 0.38461(13) 0.0233(4) Uani 1 1 d . . . C7 C -0.0105(3) 0.05131(9) 0.37383(14) 0.0249(4) Uani 1 1 d . . . C8 C 0.0806(3) 0.00409(9) 0.40048(14) 0.0255(4) Uani 1 1 d . . . C9 C -0.0183(3) 0.13643(9) 0.20654(14) 0.0277(5) Uani 1 1 d . . . C10 C -0.1763(3) 0.13501(9) 0.14279(14) 0.0285(5) Uani 1 1 d . . . C11 C -0.1752(3) 0.10997(9) 0.06116(15) 0.0321(5) Uani 1 1 d . . . C12 C -0.3271(4) 0.10799(11) 0.00113(17) 0.0421(6) Uani 1 1 d . . . H12 H -0.3255 0.0921 -0.0549 0.051 Uiso 1 1 calc R . . C13 C -0.4795(4) 0.12901(11) 0.02300(18) 0.0469(7) Uani 1 1 d . . . H13 H -0.5829 0.1272 -0.0182 0.056 Uiso 1 1 calc R . . C14 C -0.4853(3) 0.15272(11) 0.10364(17) 0.0434(6) Uani 1 1 d . . . H14 H -0.5917 0.1669 0.1180 0.052 Uiso 1 1 calc R . . C15 C -0.3351(3) 0.15562(10) 0.16290(16) 0.0350(5) Uani 1 1 d . . . H15 H -0.3387 0.1718 0.2184 0.042 Uiso 1 1 calc R . . C16 C 0.4403(3) 0.09756(9) 0.45194(14) 0.0252(4) Uani 1 1 d . . . C17 C 0.4908(3) 0.15215(9) 0.42385(14) 0.0253(4) Uani 1 1 d . . . C18 C 0.6100(3) 0.18384(9) 0.48144(15) 0.0296(5) Uani 1 1 d . . . C19 C 0.6458(3) 0.23804(10) 0.45990(16) 0.0349(5) Uani 1 1 d . . . H19 H 0.7207 0.2602 0.4999 0.042 Uiso 1 1 calc R . . C20 C 0.5733(3) 0.25958(10) 0.38112(17) 0.0369(6) Uani 1 1 d . . . H20 H 0.5983 0.2968 0.3671 0.044 Uiso 1 1 calc R . . C21 C 0.4640(3) 0.22790(9) 0.32143(16) 0.0343(5) Uani 1 1 d . . . H21 H 0.4176 0.2428 0.2661 0.041 Uiso 1 1 calc R . . C22 C 0.4232(3) 0.17452(9) 0.34318(15) 0.0289(5) Uani 1 1 d . . . H22 H 0.3482 0.1528 0.3026 0.035 Uiso 1 1 calc R . . C1S C 0.3424(4) 0.45049(12) 0.32111(19) 0.0478(7) Uani 1 1 d . . . C2S C 0.3619(4) 0.40094(13) 0.27849(19) 0.0552(8) Uani 1 1 d . . . H2S H 0.2707 0.3744 0.2737 0.066 Uiso 1 1 calc R . . C3S C 0.5097(5) 0.38927(15) 0.2431(2) 0.0650(9) Uani 1 1 d . . . H3S H 0.5202 0.3550 0.2141 0.078 Uiso 1 1 calc R . . C4S C 0.6413(5) 0.42705(17) 0.2496(2) 0.0703(10) Uani 1 1 d . . . H4S H 0.7440 0.4189 0.2254 0.084 Uiso 1 1 calc R . . C5S C 0.6266(4) 0.47719(17) 0.2912(2) 0.0691(10) Uani 1 1 d . . . H5S H 0.7180 0.5037 0.2954 0.083 Uiso 1 1 calc R . . C6S C 0.4769(4) 0.48807(13) 0.3266(2) 0.0593(8) Uani 1 1 d . . . H6S H 0.4665 0.5224 0.3554 0.071 Uiso 1 1 calc R . . C7S C 0.1776(5) 0.46249(16) 0.3573(3) 0.0812(12) Uani 1 1 d . . . H7SA H 0.2061 0.4788 0.4156 0.097 Uiso 1 1 calc R . . H7SB H 0.1128 0.4280 0.3612 0.097 Uiso 1 1 calc R . . H7SC H 0.1062 0.4885 0.3189 0.097 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 Br 0.04648(15) 0.03027(13) 0.03818(15) 0.00991(10) 0.00479(11) 0.00960(10) Cl1 0.0419(3) 0.0211(3) 0.0454(3) -0.0066(2) 0.0101(3) 0.0001(2) Cl2 0.0417(3) 0.0318(3) 0.0240(3) -0.0032(2) 0.0040(2) -0.0015(2) Cl3 0.0236(3) 0.0365(3) 0.0462(4) -0.0002(3) 0.0040(2) -0.0007(2) Cl4 0.0373(3) 0.0219(3) 0.0389(3) 0.0001(2) 0.0044(2) -0.0065(2) O1 0.0364(9) 0.0427(10) 0.0334(9) -0.0068(8) 0.0052(7) 0.0113(8) O2 0.0526(11) 0.0413(10) 0.0301(10) -0.0059(8) 0.0096(9) 0.0025(9) O3 0.0332(9) 0.0238(8) 0.0391(9) 0.0025(7) -0.0067(7) 0.0007(7) O4 0.0478(11) 0.0277(10) 0.0471(11) 0.0001(8) -0.0140(8) -0.0088(8) N1 0.0262(9) 0.0189(9) 0.0244(9) -0.0001(7) 0.0044(7) 0.0026(7) N2 0.0284(10) 0.0189(9) 0.0294(10) 0.0023(8) -0.0004(8) 0.0019(8) C1 0.0236(10) 0.0263(11) 0.0256(11) 0.0007(9) 0.0029(8) 0.0037(8) C2 0.0265(11) 0.0248(11) 0.0286(12) 0.0050(9) 0.0052(9) 0.0050(9) C3 0.0283(11) 0.0206(10) 0.0346(12) -0.0035(9) 0.0098(9) 0.0007(9) C4 0.0247(10) 0.0243(11) 0.0240(11) -0.0036(9) 0.0053(8) -0.0015(8) C5 0.0273(11) 0.0185(10) 0.0256(11) -0.0002(8) 0.0032(8) 0.0003(8) C6 0.0279(11) 0.0202(10) 0.0218(11) 0.0000(8) 0.0038(8) 0.0005(8) C7 0.0234(10) 0.0263(11) 0.0251(11) -0.0013(9) 0.0037(8) 0.0000(8) C8 0.0296(11) 0.0212(10) 0.0258(11) -0.0014(9) 0.0044(9) -0.0039(9) C9 0.0313(12) 0.0259(11) 0.0268(11) 0.0031(9) 0.0073(9) 0.0029(9) C10 0.0347(12) 0.0261(11) 0.0244(11) 0.0012(9) 0.0031(9) -0.0011(9) C11 0.0423(13) 0.0263(12) 0.0279(12) 0.0001(9) 0.0061(10) -0.0035(10) C12 0.0562(16) 0.0367(14) 0.0311(13) -0.0049(11) -0.0010(12) -0.0090(12) C13 0.0452(15) 0.0484(16) 0.0422(16) 0.0008(13) -0.0100(12) -0.0091(13) C14 0.0334(13) 0.0486(16) 0.0462(16) -0.0006(13) -0.0002(11) -0.0017(12) C15 0.0351(13) 0.0357(13) 0.0339(13) -0.0005(10) 0.0043(10) 0.0007(10) C16 0.0275(11) 0.0213(11) 0.0265(11) -0.0039(9) 0.0028(9) 0.0032(8) C17 0.0234(10) 0.0204(10) 0.0332(12) -0.0027(9) 0.0078(9) 0.0015(8) C18 0.0264(11) 0.0266(12) 0.0358(13) -0.0014(10) 0.0041(9) 0.0015(9) C19 0.0322(12) 0.0266(12) 0.0464(15) -0.0050(11) 0.0072(11) -0.0064(10) C20 0.0396(13) 0.0246(12) 0.0494(15) 0.0020(11) 0.0158(12) -0.0027(10) C21 0.0354(13) 0.0325(12) 0.0372(13) 0.0070(10) 0.0125(10) 0.0028(10) C22 0.0258(11) 0.0304(12) 0.0318(12) -0.0006(10) 0.0084(9) 0.0001(9) C1S 0.0540(17) 0.0445(16) 0.0458(16) 0.0162(13) 0.0108(13) 0.0158(13) C2S 0.0643(19) 0.0499(18) 0.0515(18) 0.0129(14) 0.0089(15) 0.0087(15) C3S 0.083(2) 0.068(2) 0.0485(18) 0.0117(16) 0.0230(17) 0.0216(19) C4S 0.072(2) 0.081(3) 0.063(2) 0.0217(19) 0.0280(18) 0.016(2) C5S 0.057(2) 0.081(3) 0.067(2) 0.0338(19) 0.0012(17) -0.0082(18) C6S 0.072(2) 0.0477(17) 0.0547(19) 0.0121(15) -0.0016(16) 0.0049(16) C7S 0.077(2) 0.078(3) 0.095(3) 0.024(2) 0.036(2) 0.028(2) _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 Br C2 1.862(2) . ? Cl1 C3 1.709(2) . ? Cl2 C4 1.694(2) . ? Cl3 C7 1.702(2) . ? Cl4 C8 1.696(2) . ? O1 C9 1.240(3) . ? O2 C11 1.348(3) . ? O3 C16 1.239(3) . ? O4 C18 1.344(3) . ? N1 C4 1.369(3) . ? N1 C1 1.395(3) . ? N1 C6 1.411(3) . ? N2 C8 1.345(3) . ? N2 C5 1.376(3) . ? C1 C2 1.376(3) . ? C1 C9 1.478(3) . ? C2 C3 1.404(3) . ? C3 C4 1.361(3) . ? C5 C6 1.386(3) . ? C5 C16 1.463(3) . ? C6 C7 1.399(3) . ? C7 C8 1.372(3) . ? C9 C10 1.458(3) . ? C10 C11 1.403(3) . ? C10 C15 1.406(3) . ? C11 C12 1.391(3) . ? C12 C13 1.375(4) . ? C13 C14 1.381(4) . ? C14 C15 1.376(3) . ? C16 C17 1.459(3) . ? C17 C22 1.391(3) . ? C17 C18 1.412(3) . ? C18 C19 1.388(3) . ? C19 C20 1.369(3) . ? C20 C21 1.389(3) . ? C21 C22 1.380(3) . ? C1S C6S 1.376(4) . ? C1S C2S 1.385(4) . ? C1S C7S 1.500(4) . ? C2S C3S 1.372(4) . ? C3S C4S 1.362(5) . ? C4S C5S 1.384(5) . ? C5S C6S 1.382(5) . ? 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 C4 N1 C1 108.61(17) . . ? C4 N1 C6 126.99(17) . . ? C1 N1 C6 124.40(17) . . ? C8 N2 C5 109.80(18) . . ? C2 C1 N1 106.65(18) . . ? C2 C1 C9 131.1(2) . . ? N1 C1 C9 120.90(18) . . ? C1 C2 C3 108.54(18) . . ? C1 C2 Br 126.21(17) . . ? C3 C2 Br 125.16(16) . . ? C4 C3 C2 107.21(19) . . ? C4 C3 Cl1 125.98(18) . . ? C2 C3 Cl1 126.80(17) . . ? C3 C4 N1 108.95(18) . . ? C3 C4 Cl2 128.34(17) . . ? N1 C4 Cl2 122.67(16) . . ? N2 C5 C6 106.49(18) . . ? N2 C5 C16 117.92(18) . . ? C6 C5 C16 134.96(19) . . ? C5 C6 C7 107.99(18) . . ? C5 C6 N1 127.74(19) . . ? C7 C6 N1 124.24(18) . . ? C8 C7 C6 106.90(18) . . ? C8 C7 Cl3 125.82(16) . . ? C6 C7 Cl3 127.26(16) . . ? N2 C8 C7 108.80(18) . . ? N2 C8 Cl4 122.53(17) . . ? C7 C8 Cl4 128.67(17) . . ? O1 C9 C10 121.8(2) . . ? O1 C9 C1 117.8(2) . . ? C10 C9 C1 120.43(19) . . ? C11 C10 C15 118.3(2) . . ? C11 C10 C9 120.3(2) . . ? C15 C10 C9 121.3(2) . . ? O2 C11 C12 117.7(2) . . ? O2 C11 C10 122.2(2) . . ? C12 C11 C10 120.1(2) . . ? C13 C12 C11 119.9(2) . . ? C12 C13 C14 121.3(2) . . ? C15 C14 C13 119.2(2) . . ? C14 C15 C10 121.2(2) . . ? O3 C16 C17 121.34(19) . . ? O3 C16 C5 117.76(19) . . ? C17 C16 C5 120.87(18) . . ? C22 C17 C18 118.9(2) . . ? C22 C17 C16 122.4(2) . . ? C18 C17 C16 118.7(2) . . ? O4 C18 C19 117.9(2) . . ? O4 C18 C17 122.5(2) . . ? C19 C18 C17 119.6(2) . . ? C20 C19 C18 120.1(2) . . ? C19 C20 C21 121.0(2) . . ? C22 C21 C20 119.4(2) . . ? C21 C22 C17 120.8(2) . . ? C6S C1S C2S 117.6(3) . . ? C6S C1S C7S 122.1(3) . . ? C2S C1S C7S 120.3(3) . . ? C3S C2S C1S 121.6(3) . . ? C4S C3S C2S 119.7(3) . . ? C3S C4S C5S 120.5(3) . . ? C6S C5S C4S 118.9(3) . . ? C1S C6S C5S 121.7(3) . . ? 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 C4 N1 C1 C2 1.2(2) . . . . ? C6 N1 C1 C2 -179.01(18) . . . . ? C4 N1 C1 C9 169.53(18) . . . . ? C6 N1 C1 C9 -10.6(3) . . . . ? N1 C1 C2 C3 -0.1(2) . . . . ? C9 C1 C2 C3 -166.9(2) . . . . ? N1 C1 C2 Br 176.74(15) . . . . ? C9 C1 C2 Br 10.0(4) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? Br C2 C3 C4 -177.85(15) . . . . ? C1 C2 C3 Cl1 178.65(17) . . . . ? Br C2 C3 Cl1 1.7(3) . . . . ? C2 C3 C4 N1 1.7(2) . . . . ? Cl1 C3 C4 N1 -177.92(16) . . . . ? C2 C3 C4 Cl2 -176.05(16) . . . . ? Cl1 C3 C4 Cl2 4.4(3) . . . . ? C1 N1 C4 C3 -1.8(2) . . . . ? C6 N1 C4 C3 178.39(19) . . . . ? C1 N1 C4 Cl2 176.10(15) . . . . ? C6 N1 C4 Cl2 -3.7(3) . . . . ? C8 N2 C5 C6 1.8(2) . . . . ? C8 N2 C5 C16 174.08(19) . . . . ? N2 C5 C6 C7 -1.1(2) . . . . ? C16 C5 C6 C7 -171.5(2) . . . . ? N2 C5 C6 N1 176.71(19) . . . . ? C16 C5 C6 N1 6.4(4) . . . . ? C4 N1 C6 C5 -58.3(3) . . . . ? C1 N1 C6 C5 121.9(2) . . . . ? C4 N1 C6 C7 119.3(2) . . . . ? C1 N1 C6 C7 -60.5(3) . . . . ? C5 C6 C7 C8 0.1(2) . . . . ? N1 C6 C7 C8 -177.84(19) . . . . ? C5 C6 C7 Cl3 178.27(17) . . . . ? N1 C6 C7 Cl3 0.3(3) . . . . ? C5 N2 C8 C7 -1.8(3) . . . . ? C5 N2 C8 Cl4 178.47(16) . . . . ? C6 C7 C8 N2 1.0(2) . . . . ? Cl3 C7 C8 N2 -177.19(16) . . . . ? C6 C7 C8 Cl4 -179.25(17) . . . . ? Cl3 C7 C8 Cl4 2.5(3) . . . . ? C2 C1 C9 O1 122.1(3) . . . . ? N1 C1 C9 O1 -43.0(3) . . . . ? C2 C1 C9 C10 -58.5(3) . . . . ? N1 C1 C9 C10 136.4(2) . . . . ? O1 C9 C10 C11 -12.0(3) . . . . ? C1 C9 C10 C11 168.6(2) . . . . ? O1 C9 C10 C15 164.3(2) . . . . ? C1 C9 C10 C15 -15.0(3) . . . . ? C15 C10 C11 O2 -178.1(2) . . . . ? C9 C10 C11 O2 -1.6(3) . . . . ? C15 C10 C11 C12 2.6(3) . . . . ? C9 C10 C11 C12 179.0(2) . . . . ? O2 C11 C12 C13 178.5(2) . . . . ? C10 C11 C12 C13 -2.1(4) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C10 0.1(4) . . . . ? C11 C10 C15 C14 -1.6(4) . . . . ? C9 C10 C15 C14 -178.0(2) . . . . ? N2 C5 C16 O3 -18.7(3) . . . . ? C6 C5 C16 O3 150.8(2) . . . . ? N2 C5 C16 C17 163.39(19) . . . . ? C6 C5 C16 C17 -27.1(4) . . . . ? O3 C16 C17 C22 155.7(2) . . . . ? C5 C16 C17 C22 -26.4(3) . . . . ? O3 C16 C17 C18 -25.6(3) . . . . ? C5 C16 C17 C18 152.3(2) . . . . ? C22 C17 C18 O4 -176.1(2) . . . . ? C16 C17 C18 O4 5.2(3) . . . . ? C22 C17 C18 C19 5.5(3) . . . . ? C16 C17 C18 C19 -173.3(2) . . . . ? O4 C18 C19 C20 177.9(2) . . . . ? C17 C18 C19 C20 -3.6(3) . . . . ? C18 C19 C20 C21 -0.2(4) . . . . ? C19 C20 C21 C22 2.2(3) . . . . ? C20 C21 C22 C17 -0.2(3) . . . . ? C18 C17 C22 C21 -3.6(3) . . . . ? C16 C17 C22 C21 175.1(2) . . . . ? C6S C1S C2S C3S 0.2(4) . . . . ? C7S C1S C2S C3S 178.6(3) . . . . ? C1S C2S C3S C4S 0.0(5) . . . . ? C2S C3S C4S C5S -0.4(5) . . . . ? C3S C4S C5S C6S 0.5(5) . . . . ? C2S C1S C6S C5S -0.1(4) . . . . ? C7S C1S C6S C5S -178.5(3) . . . . ? C4S C5S C6S C1S -0.2(5) . . . . ? 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 O2 H2O O1 0.83(3) 1.88(3) 2.607(3) 145(3) . O4 H4O O3 0.71(3) 2.00(3) 2.612(2) 145(3) . N2 H2N O3 0.82(3) 2.00(3) 2.800(2) 166(3) 3_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.754 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.058 data_11 _database_code_depnum_ccdc_archive 'CCDC 900767' #TrackingRef '13856_web_deposit_cif_file_0_RobertMcDonald_1347316575.dlcacie.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 Br Cl2 N2 O4' _chemical_formula_sum 'C12 H9 Br Cl2 N2 O4' _chemical_formula_weight 396.02 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' Cl Cl 0.1484 0.1585 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5864(4) _cell_length_b 9.0677(5) _cell_length_c 12.2844(7) _cell_angle_alpha 77.0064(6) _cell_angle_beta 75.9683(6) _cell_angle_gamma 65.5279(6) _cell_volume 738.75(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3886 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.46 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 3.159 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.4027 _exptl_absorpt_correction_T_max 0.5595 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6270 _diffrn_reflns_av_R_equivalents 0.0130 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3328 _reflns_number_gt 3064 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'DIRDIF-2008 (Beurskens et al., 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0348P)^2^+0.3700P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3328 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br -0.34614(3) 0.64188(2) 0.439868(17) 0.02827(8) Uani 1 1 d . . . Cl1 Cl -0.14220(7) 0.21947(6) 0.49567(4) 0.02939(12) Uani 1 1 d . . . Cl2 Cl 0.33044(8) 0.08185(6) 0.35324(5) 0.03577(14) Uani 1 1 d . . . O1 O 0.1642(2) 0.73059(19) 0.16260(13) 0.0364(4) Uani 1 1 d . . . O2 O -0.0943(2) 0.83092(17) 0.29530(13) 0.0317(3) Uani 1 1 d . . . O3 O 0.1656(2) 0.2974(3) 0.08639(16) 0.0469(5) Uani 1 1 d . . . O4 O 0.4443(2) 0.2140(2) -0.03875(13) 0.0361(4) Uani 1 1 d . . . N1 N 0.2117(2) 0.4056(2) 0.28636(13) 0.0217(3) Uani 1 1 d . . . N2 N 0.6312(2) 0.3252(2) 0.06604(14) 0.0249(3) Uani 1 1 d . . . H2N H 0.6998 0.2916 0.0013 0.030 Uiso 1 1 calc R . . C1 C 0.0512(3) 0.5500(2) 0.30564(16) 0.0208(4) Uani 1 1 d . . . C2 C -0.0939(3) 0.5078(2) 0.38115(15) 0.0212(4) Uani 1 1 d . . . C3 C -0.0220(3) 0.3368(2) 0.40738(16) 0.0233(4) Uani 1 1 d . . . C4 C 0.1660(3) 0.2782(2) 0.34889(17) 0.0235(4) Uani 1 1 d . . . C5 C 0.4463(3) 0.3283(2) 0.11048(16) 0.0229(4) Uani 1 1 d . . . C6 C 0.3929(3) 0.3881(2) 0.21211(16) 0.0219(4) Uani 1 1 d . . . C7 C 0.5480(3) 0.4208(2) 0.23004(18) 0.0267(4) Uani 1 1 d . . . H7 H 0.5523 0.4617 0.2937 0.032 Uiso 1 1 calc R . . C8 C 0.6927(3) 0.3819(3) 0.13679(18) 0.0284(4) Uani 1 1 d . . . H8 H 0.8155 0.3929 0.1241 0.034 Uiso 1 1 calc R . . C9 C 0.0505(3) 0.7098(2) 0.24597(16) 0.0227(4) Uani 1 1 d . . . C10 C -0.1067(4) 0.9946(3) 0.2458(2) 0.0394(5) Uani 1 1 d . . . H10A H -0.2186 1.0741 0.2883 0.047 Uiso 1 1 calc R . . H10B H -0.1247 1.0143 0.1667 0.047 Uiso 1 1 calc R . . H10C H 0.0146 1.0063 0.2488 0.047 Uiso 1 1 calc R . . C11 C 0.3347(3) 0.2802(3) 0.05412(17) 0.0278(4) Uani 1 1 d . . . C12 C 0.3428(5) 0.1757(4) -0.1067(2) 0.0560(8) Uani 1 1 d . . . H12A H 0.4348 0.1302 -0.1732 0.067 Uiso 1 1 calc R . . H12B H 0.2355 0.2756 -0.1315 0.067 Uiso 1 1 calc R . . H12C H 0.2889 0.0953 -0.0617 0.067 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 Br 0.02044(11) 0.02951(12) 0.02815(12) -0.00677(8) 0.00419(8) -0.00613(8) Cl1 0.0240(2) 0.0267(2) 0.0329(3) 0.00135(19) 0.00447(19) -0.0131(2) Cl2 0.0284(3) 0.0197(2) 0.0461(3) -0.0022(2) 0.0075(2) -0.0051(2) O1 0.0377(9) 0.0275(8) 0.0320(8) -0.0005(6) 0.0106(7) -0.0116(7) O2 0.0313(8) 0.0199(7) 0.0352(8) -0.0043(6) 0.0049(6) -0.0069(6) O3 0.0256(8) 0.0732(13) 0.0486(10) -0.0218(9) -0.0021(7) -0.0209(9) O4 0.0386(9) 0.0436(9) 0.0275(8) -0.0112(7) -0.0029(7) -0.0156(8) N1 0.0190(8) 0.0210(8) 0.0216(8) -0.0032(6) 0.0028(6) -0.0075(6) N2 0.0184(8) 0.0244(8) 0.0237(8) -0.0007(6) 0.0037(6) -0.0056(7) C1 0.0191(9) 0.0218(9) 0.0197(9) -0.0052(7) -0.0001(7) -0.0067(7) C2 0.0177(9) 0.0241(9) 0.0185(9) -0.0047(7) 0.0008(7) -0.0059(7) C3 0.0216(9) 0.0238(9) 0.0227(9) -0.0022(7) 0.0014(7) -0.0103(8) C4 0.0213(9) 0.0195(9) 0.0269(10) -0.0035(7) 0.0007(7) -0.0074(8) C5 0.0173(9) 0.0229(9) 0.0219(9) 0.0005(7) 0.0006(7) -0.0053(7) C6 0.0178(9) 0.0200(9) 0.0235(9) -0.0011(7) 0.0010(7) -0.0064(7) C7 0.0252(10) 0.0252(10) 0.0298(10) -0.0028(8) -0.0032(8) -0.0111(8) C8 0.0196(9) 0.0272(10) 0.0356(11) 0.0017(8) -0.0018(8) -0.0108(8) C9 0.0210(9) 0.0240(9) 0.0219(9) -0.0034(7) -0.0022(7) -0.0079(8) C10 0.0409(13) 0.0186(10) 0.0528(15) -0.0020(9) -0.0055(11) -0.0084(10) C11 0.0285(11) 0.0290(10) 0.0245(10) -0.0017(8) -0.0044(8) -0.0105(9) C12 0.072(2) 0.0642(19) 0.0422(15) -0.0182(13) -0.0207(14) -0.0242(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br C2 1.8594(19) . ? Cl1 C3 1.7158(19) . ? Cl2 C4 1.697(2) . ? O1 C9 1.203(2) . ? O2 C9 1.326(2) . ? O2 C10 1.445(3) . ? O3 C11 1.201(3) . ? O4 C11 1.337(3) . ? O4 C12 1.441(3) . ? N1 C4 1.360(2) . ? N1 C1 1.390(2) . ? N1 C6 1.423(2) . ? N2 C8 1.353(3) . ? N2 C5 1.367(2) . ? C1 C2 1.383(3) . ? C1 C9 1.468(3) . ? C2 C3 1.402(3) . ? C3 C4 1.371(3) . ? C5 C6 1.376(3) . ? C5 C11 1.454(3) . ? C6 C7 1.401(3) . ? C7 C8 1.376(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O2 C10 116.24(17) . . ? C11 O4 C12 115.8(2) . . ? C4 N1 C1 108.38(15) . . ? C4 N1 C6 124.18(16) . . ? C1 N1 C6 127.41(16) . . ? C8 N2 C5 109.70(17) . . ? C2 C1 N1 107.28(16) . . ? C2 C1 C9 130.89(18) . . ? N1 C1 C9 121.74(16) . . ? C1 C2 C3 107.97(17) . . ? C1 C2 Br 129.27(15) . . ? C3 C2 Br 122.74(14) . . ? C4 C3 C2 107.00(17) . . ? C4 C3 Cl1 125.52(16) . . ? C2 C3 Cl1 127.49(15) . . ? N1 C4 C3 109.37(17) . . ? N1 C4 Cl2 122.25(15) . . ? C3 C4 Cl2 128.32(15) . . ? N2 C5 C6 106.71(17) . . ? N2 C5 C11 123.84(18) . . ? C6 C5 C11 129.43(18) . . ? C5 C6 C7 108.70(17) . . ? C5 C6 N1 124.05(17) . . ? C7 C6 N1 127.20(18) . . ? C8 C7 C6 106.10(19) . . ? N2 C8 C7 108.78(18) . . ? O1 C9 O2 123.58(18) . . ? O1 C9 C1 125.28(18) . . ? O2 C9 C1 111.14(16) . . ? O3 C11 O4 124.1(2) . . ? O3 C11 C5 124.6(2) . . ? O4 C11 C5 111.35(18) . . ? 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 C4 N1 C1 C2 -0.2(2) . . . . ? C6 N1 C1 C2 177.99(18) . . . . ? C4 N1 C1 C9 -176.99(17) . . . . ? C6 N1 C1 C9 1.2(3) . . . . ? N1 C1 C2 C3 -0.4(2) . . . . ? C9 C1 C2 C3 175.98(19) . . . . ? N1 C1 C2 Br -178.77(14) . . . . ? C9 C1 C2 Br -2.3(3) . . . . ? C1 C2 C3 C4 0.9(2) . . . . ? Br C2 C3 C4 179.34(14) . . . . ? C1 C2 C3 Cl1 -179.27(15) . . . . ? Br C2 C3 Cl1 -0.8(3) . . . . ? C1 N1 C4 C3 0.7(2) . . . . ? C6 N1 C4 C3 -177.50(18) . . . . ? C1 N1 C4 Cl2 -176.57(15) . . . . ? C6 N1 C4 Cl2 5.2(3) . . . . ? C2 C3 C4 N1 -1.0(2) . . . . ? Cl1 C3 C4 N1 179.14(15) . . . . ? C2 C3 C4 Cl2 176.10(16) . . . . ? Cl1 C3 C4 Cl2 -3.8(3) . . . . ? C8 N2 C5 C6 -0.3(2) . . . . ? C8 N2 C5 C11 178.07(18) . . . . ? N2 C5 C6 C7 -0.4(2) . . . . ? C11 C5 C6 C7 -178.60(19) . . . . ? N2 C5 C6 N1 -178.08(17) . . . . ? C11 C5 C6 N1 3.7(3) . . . . ? C4 N1 C6 C5 71.3(3) . . . . ? C1 N1 C6 C5 -106.6(2) . . . . ? C4 N1 C6 C7 -105.9(2) . . . . ? C1 N1 C6 C7 76.2(3) . . . . ? C5 C6 C7 C8 0.9(2) . . . . ? N1 C6 C7 C8 178.48(19) . . . . ? C5 N2 C8 C7 0.8(2) . . . . ? C6 C7 C8 N2 -1.0(2) . . . . ? C10 O2 C9 O1 -2.2(3) . . . . ? C10 O2 C9 C1 178.36(18) . . . . ? C2 C1 C9 O1 -160.9(2) . . . . ? N1 C1 C9 O1 15.1(3) . . . . ? C2 C1 C9 O2 18.5(3) . . . . ? N1 C1 C9 O2 -165.47(17) . . . . ? C12 O4 C11 O3 5.4(3) . . . . ? C12 O4 C11 C5 -174.6(2) . . . . ? N2 C5 C11 O3 -172.2(2) . . . . ? C6 C5 C11 O3 5.7(4) . . . . ? N2 C5 C11 O4 7.7(3) . . . . ? C6 C5 C11 O4 -174.34(19) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.385 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.064 data_17 _database_code_depnum_ccdc_archive 'CCDC 900768' #TrackingRef '13856_web_deposit_cif_file_0_RobertMcDonald_1347316575.dlcacie.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 Br Cl2 N O5' _chemical_formula_sum 'C13 H12 Br Cl2 N O5' _chemical_formula_weight 413.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.38720(10) _cell_length_b 10.2210(2) _cell_length_c 14.5246(3) _cell_angle_alpha 90.2868(7) _cell_angle_beta 94.2793(5) _cell_angle_gamma 100.6247(5) _cell_volume 783.72(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9931 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 69.62 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.750 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 6.928 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1046 _exptl_absorpt_correction_T_max 0.5937 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5241 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 70.02 _reflns_number_total 2820 _reflns_number_gt 2763 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'DIRDIF-2008 (Beurskens et al., 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0798P)^2^+0.4414P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2820 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br -0.24951(5) 0.54166(3) 0.095756(19) 0.03169(17) Uani 1 1 d . . . Cl1 Cl 0.15435(14) 0.68169(7) 0.28480(5) 0.0328(2) Uani 1 1 d . . . Cl2 Cl 0.54803(13) 0.47246(7) 0.35195(5) 0.0324(2) Uani 1 1 d . . . O1 O 0.1104(4) 0.1589(2) 0.05305(15) 0.0364(5) Uani 1 1 d . . . O2 O -0.2327(4) 0.2543(2) 0.03028(13) 0.0298(4) Uani 1 1 d . . . O3 O 0.2314(4) 0.1625(2) 0.35389(13) 0.0280(4) Uani 1 1 d . . . O4 O 0.5166(5) -0.0436(2) 0.35466(15) 0.0393(5) Uani 1 1 d . . . O5 O 0.6936(4) 0.0406(2) 0.22742(15) 0.0350(5) Uani 1 1 d . . . N N 0.2696(4) 0.3353(2) 0.20907(15) 0.0230(5) Uani 1 1 d . . . C1 C 0.0737(5) 0.3473(3) 0.14355(18) 0.0231(5) Uani 1 1 d . . . C2 C 0.0002(5) 0.4664(3) 0.16080(17) 0.0233(5) Uani 1 1 d . . . C3 C 0.1521(5) 0.5290(3) 0.23689(17) 0.0238(5) Uani 1 1 d . . . C4 C 0.3147(5) 0.4452(3) 0.26533(17) 0.0235(5) Uani 1 1 d . . . C5 C -0.0099(5) 0.2429(3) 0.07164(17) 0.0248(6) Uani 1 1 d . . . C6 C -0.3273(6) 0.1612(4) -0.0464(2) 0.0373(7) Uani 1 1 d . . . H6A H -0.4916 0.1780 -0.0721 0.045 Uiso 1 1 calc R . . H6B H -0.3469 0.0698 -0.0241 0.045 Uiso 1 1 calc R . . H6C H -0.2068 0.1734 -0.0943 0.045 Uiso 1 1 calc R . . C7 C 0.4079(5) 0.2290(3) 0.21627(18) 0.0246(5) Uani 1 1 d . . . H7 H 0.5092 0.2135 0.1680 0.030 Uiso 1 1 calc R . . C8 C 0.3970(5) 0.1514(3) 0.28951(18) 0.0238(5) Uani 1 1 d . . . C9 C 0.3040(6) 0.1488(3) 0.45070(19) 0.0319(6) Uani 1 1 d . . . H9A H 0.4883 0.1812 0.4634 0.038 Uiso 1 1 calc R . . H9B H 0.2648 0.0540 0.4679 0.038 Uiso 1 1 calc R . . C10 C 0.1595(6) 0.2288(3) 0.5052(2) 0.0343(7) Uani 1 1 d . . . H10 H 0.1839 0.2253 0.5705 0.041 Uiso 1 1 calc R . . C11 C 0.0025(7) 0.3035(4) 0.4718(2) 0.0395(7) Uani 1 1 d . . . H11A H -0.0282 0.3102 0.4069 0.047 Uiso 1 1 calc R . . H11B H -0.0808 0.3509 0.5125 0.047 Uiso 1 1 calc R . . C12 C 0.5419(5) 0.0393(3) 0.29622(18) 0.0268(6) Uani 1 1 d . . . C13 C 0.8332(6) -0.0670(3) 0.2278(2) 0.0363(7) Uani 1 1 d . . . H13A H 0.9393 -0.0585 0.1754 0.044 Uiso 1 1 calc R . . H13B H 0.7144 -0.1522 0.2228 0.044 Uiso 1 1 calc R . . H13C H 0.9409 -0.0635 0.2856 0.044 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 Br 0.0298(2) 0.0373(3) 0.0315(2) 0.00780(15) 0.00676(14) 0.01343(15) Cl1 0.0431(4) 0.0262(4) 0.0314(4) -0.0024(3) 0.0099(3) 0.0099(3) Cl2 0.0281(4) 0.0371(4) 0.0307(3) -0.0010(3) -0.0015(3) 0.0041(3) O1 0.0378(12) 0.0344(12) 0.0394(11) -0.0084(9) 0.0022(9) 0.0136(9) O2 0.0261(10) 0.0392(12) 0.0244(9) -0.0059(8) 0.0045(7) 0.0057(8) O3 0.0262(10) 0.0380(11) 0.0222(9) 0.0041(8) 0.0076(7) 0.0097(8) O4 0.0534(14) 0.0333(12) 0.0362(11) 0.0084(10) 0.0116(10) 0.0178(10) O5 0.0357(11) 0.0379(12) 0.0384(11) 0.0069(9) 0.0137(9) 0.0204(9) N 0.0216(11) 0.0260(12) 0.0229(10) 0.0019(9) 0.0069(8) 0.0063(9) C1 0.0211(12) 0.0307(14) 0.0194(11) 0.0041(10) 0.0084(9) 0.0071(10) C2 0.0212(12) 0.0300(14) 0.0211(11) 0.0052(10) 0.0080(9) 0.0081(10) C3 0.0251(13) 0.0250(13) 0.0236(12) 0.0011(10) 0.0112(10) 0.0066(10) C4 0.0215(12) 0.0273(14) 0.0222(11) 0.0013(10) 0.0066(9) 0.0041(10) C5 0.0246(13) 0.0288(15) 0.0212(12) 0.0024(11) 0.0074(10) 0.0030(10) C6 0.0352(16) 0.048(2) 0.0266(14) -0.0085(13) 0.0024(12) 0.0015(14) C7 0.0228(13) 0.0282(14) 0.0250(12) 0.0001(11) 0.0061(10) 0.0085(10) C8 0.0211(12) 0.0274(14) 0.0241(12) -0.0019(10) 0.0046(9) 0.0062(10) C9 0.0362(15) 0.0400(17) 0.0220(13) 0.0051(12) 0.0058(11) 0.0117(12) C10 0.0397(17) 0.0413(17) 0.0235(13) 0.0019(12) 0.0092(11) 0.0088(13) C11 0.0392(18) 0.051(2) 0.0323(15) -0.0009(14) 0.0118(13) 0.0159(14) C12 0.0253(13) 0.0290(14) 0.0268(12) -0.0007(11) 0.0016(10) 0.0070(10) C13 0.0332(16) 0.0351(17) 0.0452(17) -0.0002(14) 0.0064(12) 0.0171(13) _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 Br C2 1.869(3) . ? Cl1 C3 1.703(3) . ? Cl2 C4 1.695(3) . ? O1 C5 1.208(4) . ? O2 C5 1.327(3) . ? O2 C6 1.460(4) . ? O3 C8 1.358(3) . ? O3 C9 1.446(3) . ? O4 C12 1.200(4) . ? O5 C12 1.336(3) . ? O5 C13 1.443(3) . ? N C4 1.360(4) . ? N C1 1.391(4) . ? N C7 1.426(3) . ? C1 C2 1.375(4) . ? C1 C5 1.475(4) . ? C2 C3 1.402(4) . ? C3 C4 1.378(4) . ? C7 C8 1.328(4) . ? C8 C12 1.500(4) . ? C9 C10 1.491(4) . ? C10 C11 1.309(5) . ? 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 C5 O2 C6 115.9(2) . . ? C8 O3 C9 120.1(2) . . ? C12 O5 C13 114.8(2) . . ? C4 N C1 108.4(2) . . ? C4 N C7 124.7(2) . . ? C1 N C7 126.9(2) . . ? C2 C1 N 107.4(2) . . ? C2 C1 C5 132.7(3) . . ? N C1 C5 119.9(2) . . ? C1 C2 C3 108.3(2) . . ? C1 C2 Br 128.3(2) . . ? C3 C2 Br 123.4(2) . . ? C4 C3 C2 106.8(2) . . ? C4 C3 Cl1 124.7(2) . . ? C2 C3 Cl1 128.5(2) . . ? N C4 C3 109.2(2) . . ? N C4 Cl2 123.3(2) . . ? C3 C4 Cl2 127.4(2) . . ? O1 C5 O2 124.9(3) . . ? O1 C5 C1 124.1(3) . . ? O2 C5 C1 110.9(2) . . ? C8 C7 N 120.9(2) . . ? C7 C8 O3 120.2(2) . . ? C7 C8 C12 120.6(2) . . ? O3 C8 C12 118.8(2) . . ? O3 C9 C10 108.1(2) . . ? C11 C10 C9 126.4(3) . . ? O4 C12 O5 124.6(3) . . ? O4 C12 C8 123.7(3) . . ? O5 C12 C8 111.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N C1 C2 0.0(3) . . . . ? C7 N C1 C2 -178.4(2) . . . . ? C4 N C1 C5 178.3(2) . . . . ? C7 N C1 C5 -0.1(4) . . . . ? N C1 C2 C3 0.4(3) . . . . ? C5 C1 C2 C3 -177.6(3) . . . . ? N C1 C2 Br 178.71(18) . . . . ? C5 C1 C2 Br 0.7(4) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? Br C2 C3 C4 -179.08(17) . . . . ? C1 C2 C3 Cl1 176.60(19) . . . . ? Br C2 C3 Cl1 -1.8(3) . . . . ? C1 N C4 C3 -0.4(3) . . . . ? C7 N C4 C3 178.0(2) . . . . ? C1 N C4 Cl2 -177.42(18) . . . . ? C7 N C4 Cl2 1.0(4) . . . . ? C2 C3 C4 N 0.7(3) . . . . ? Cl1 C3 C4 N -176.72(18) . . . . ? C2 C3 C4 Cl2 177.50(19) . . . . ? Cl1 C3 C4 Cl2 0.1(3) . . . . ? C6 O2 C5 O1 -3.4(4) . . . . ? C6 O2 C5 C1 176.2(2) . . . . ? C2 C1 C5 O1 162.4(3) . . . . ? N C1 C5 O1 -15.4(4) . . . . ? C2 C1 C5 O2 -17.3(4) . . . . ? N C1 C5 O2 164.9(2) . . . . ? C4 N C7 C8 65.8(4) . . . . ? C1 N C7 C8 -116.0(3) . . . . ? N C7 C8 O3 7.5(4) . . . . ? N C7 C8 C12 179.6(2) . . . . ? C9 O3 C8 C7 -142.3(3) . . . . ? C9 O3 C8 C12 45.4(4) . . . . ? C8 O3 C9 C10 151.7(3) . . . . ? O3 C9 C10 C11 -2.8(5) . . . . ? C13 O5 C12 O4 -0.6(4) . . . . ? C13 O5 C12 C8 -178.2(2) . . . . ? C7 C8 C12 O4 -170.7(3) . . . . ? O3 C8 C12 O4 1.5(4) . . . . ? C7 C8 C12 O5 6.8(4) . . . . ? O3 C8 C12 O5 179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 67.80 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.698 _refine_diff_density_min -1.012 _refine_diff_density_rms 0.208 data_2a _database_code_depnum_ccdc_archive 'CCDC 900769' #TrackingRef '13856_web_deposit_cif_file_0_RobertMcDonald_1347316575.dlcacie.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H27 Br Cl2 N2 O6 S, C4 H10 O' _chemical_formula_sum 'C35 H37 Br Cl2 N2 O7 S' _chemical_formula_weight 780.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1565(4) _cell_length_b 13.5338(6) _cell_length_c 15.7518(7) _cell_angle_alpha 65.1442(5) _cell_angle_beta 83.7108(5) _cell_angle_gamma 81.8745(5) _cell_volume 1750.67(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9150 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 23.65 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.437 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.5294 _exptl_absorpt_correction_T_max 0.5743 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15885 _diffrn_reflns_av_R_equivalents 0.0117 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.57 _reflns_number_total 8023 _reflns_number_gt 6952 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'DIRDIF-2008 (Beurskens et al., 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0470P)^2^+0.7094P] 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 8023 _refine_ls_number_parameters 482 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br 0.36956(2) -0.273035(16) 0.260570(15) 0.04263(7) Uani 1 1 d . . . Cl1 Cl 0.62681(5) -0.15232(5) 0.32360(3) 0.04385(12) Uani 1 1 d . . . Cl2 Cl 0.50042(5) 0.12115(5) 0.26291(4) 0.04641(13) Uani 1 1 d . . . S S -0.13826(5) 0.36067(4) 0.16849(3) 0.03312(10) Uani 1 1 d D . . O1 O -0.00446(15) -0.10462(12) 0.23331(10) 0.0387(3) Uani 1 1 d . . . H1O H -0.051(3) -0.063(2) 0.2474(18) 0.049(7) Uiso 1 1 d . . . O2 O 0.28187(18) 0.05477(14) 0.01191(10) 0.0498(4) Uani 1 1 d . . . O3 O -0.13397(14) 0.05869(12) 0.29059(9) 0.0324(3) Uani 1 1 d . . . H3O H -0.191(3) 0.107(2) 0.2665(18) 0.050(8) Uiso 1 1 d . . . O4 O 0.19619(16) 0.12500(14) 0.40940(10) 0.0468(4) Uani 1 1 d . . . O5 O -0.24666(14) 0.28653(10) 0.21597(9) 0.0359(3) Uani 1 1 d . A . O6 O -0.15730(17) 0.43642(12) 0.07364(10) 0.0481(3) Uani 1 1 d . A . N1 N 0.27860(15) 0.04504(13) 0.21753(10) 0.0297(3) Uani 1 1 d . . . N2 N 0.02046(16) 0.28415(12) 0.16611(10) 0.0317(3) Uani 1 1 d . A . C1 C 0.24120(18) -0.04793(15) 0.21176(11) 0.0290(3) Uani 1 1 d . . . C2 C 0.35384(19) -0.12865(15) 0.24850(12) 0.0310(4) Uani 1 1 d . . . C3 C 0.46237(19) -0.08492(16) 0.27590(12) 0.0328(4) Uani 1 1 d . . . C4 C 0.41450(19) 0.02174(16) 0.25498(12) 0.0333(4) Uani 1 1 d . . . C5 C 0.06561(18) 0.17503(14) 0.22492(11) 0.0269(3) Uani 1 1 d . . . C6 C 0.19666(18) 0.14957(15) 0.18457(12) 0.0303(3) Uani 1 1 d . A . C7 C 0.2366(2) 0.24174(17) 0.10374(13) 0.0397(4) Uani 1 1 d . . . H7 H 0.3240 0.2453 0.0645 0.048 Uiso 1 1 calc R A . C8 C 0.1279(2) 0.32315(17) 0.09293(13) 0.0404(4) Uani 1 1 d . A . H8 H 0.1244 0.3948 0.0441 0.048 Uiso 1 1 calc R . . C9 C 0.10300(18) -0.04460(16) 0.16594(12) 0.0315(4) Uani 1 1 d . . . H9 H 0.0601 0.0335 0.1350 0.038 Uiso 1 1 calc R . . C10 C 0.1374(2) -0.08949(18) 0.09164(13) 0.0380(4) Uani 1 1 d . . . C11 C 0.2310(2) -0.03630(19) 0.01426(13) 0.0425(5) Uani 1 1 d . . . C12 C 0.2684(3) -0.0772(2) -0.05395(15) 0.0551(6) Uani 1 1 d . . . H12 H 0.3338 -0.0417 -0.1059 0.066 Uiso 1 1 calc R . . C13 C 0.2100(3) -0.1689(2) -0.04533(17) 0.0631(7) Uani 1 1 d . . . H13 H 0.2372 -0.1977 -0.0910 0.076 Uiso 1 1 calc R . . C14 C 0.1128(3) -0.2198(2) 0.0281(2) 0.0649(7) Uani 1 1 d . . . H14 H 0.0705 -0.2818 0.0320 0.078 Uiso 1 1 calc R . . C15 C 0.0766(3) -0.1798(2) 0.09720(17) 0.0527(6) Uani 1 1 d . . . H15 H 0.0097 -0.2150 0.1483 0.063 Uiso 1 1 calc R . . C16 C 0.3600(4) 0.1206(2) -0.07175(17) 0.0709(8) Uani 1 1 d . . . H16A H 0.3914 0.1826 -0.0642 0.085 Uiso 1 1 calc R . . H16B H 0.2953 0.1480 -0.1243 0.085 Uiso 1 1 calc R . . H16C H 0.4470 0.0765 -0.0843 0.085 Uiso 1 1 calc R . . C17 C -0.01323(18) 0.09919(14) 0.31215(11) 0.0269(3) Uani 1 1 d . A . H17 H 0.0600 0.0335 0.3400 0.032 Uiso 1 1 calc R . . C18 C -0.0563(2) 0.13893(14) 0.38963(12) 0.0303(3) Uani 1 1 d . . . C19 C 0.0551(2) 0.14903(16) 0.43834(12) 0.0366(4) Uani 1 1 d . A . C20 C 0.0196(3) 0.17983(18) 0.51303(14) 0.0493(5) Uani 1 1 d . . . H20 H 0.0960 0.1883 0.5449 0.059 Uiso 1 1 calc R A . C21 C -0.1257(3) 0.19774(19) 0.54023(15) 0.0547(6) Uani 1 1 d . A . H21 H -0.1496 0.2195 0.5905 0.066 Uiso 1 1 calc R . . C22 C -0.2364(3) 0.1845(2) 0.49544(16) 0.0563(6) Uani 1 1 d . . . H22 H -0.3367 0.1953 0.5155 0.068 Uiso 1 1 calc R A . C23 C -0.2013(2) 0.15512(18) 0.42014(14) 0.0441(5) Uani 1 1 d . A . H23 H -0.2785 0.1461 0.3892 0.053 Uiso 1 1 calc R . . C24 C 0.3101(3) 0.1092(3) 0.47083(17) 0.0659(7) Uani 1 1 d . . . H24A H 0.4061 0.0930 0.4426 0.079 Uiso 1 1 calc R . . H24B H 0.2915 0.0478 0.5310 0.079 Uiso 1 1 calc R . . H24C H 0.3105 0.1758 0.4809 0.079 Uiso 1 1 calc R . . C25A C -0.1032(4) 0.4323(4) 0.2321(4) 0.0351(5) Uani 0.65 1 d PD A 1 C26A C -0.1971(5) 0.4287(4) 0.3053(3) 0.0657(12) Uani 0.65 1 d P A 1 H26A H -0.2763 0.3841 0.3244 0.079 Uiso 0.65 1 calc PR A 1 C27A C -0.1746(6) 0.4922(4) 0.3519(3) 0.0747(14) Uani 0.65 1 d P A 1 H27A H -0.2408 0.4910 0.4031 0.090 Uiso 0.65 1 calc PR A 1 C28A C -0.0609(5) 0.5564(5) 0.3269(4) 0.0450(7) Uani 0.65 1 d PD A 1 C29A C 0.0308(4) 0.5564(4) 0.2514(4) 0.0632(11) Uani 0.65 1 d P A 1 H29A H 0.1120 0.5990 0.2326 0.076 Uiso 0.65 1 calc PR A 1 C30A C 0.0087(4) 0.4967(4) 0.2023(3) 0.0596(11) Uani 0.65 1 d P A 1 H30A H 0.0705 0.5007 0.1487 0.072 Uiso 0.65 1 calc PR A 1 C31A C -0.0399(17) 0.6224(10) 0.3806(8) 0.058(3) Uani 0.65 1 d PD A 1 H31A H -0.0516 0.7005 0.3390 0.069 Uiso 0.65 1 calc PR A 1 H31B H 0.0594 0.6021 0.4045 0.069 Uiso 0.65 1 calc PR A 1 H31C H -0.1138 0.6073 0.4332 0.069 Uiso 0.65 1 calc PR A 1 C25B C -0.1153(6) 0.4323(7) 0.2383(7) 0.0351(5) Uani 0.35 1 d PGD A 2 C26B C -0.2303(5) 0.5066(6) 0.2474(6) 0.078(3) Uani 0.35 1 d PG A 2 H26B H -0.3212 0.5156 0.2199 0.093 Uiso 0.35 1 calc PR A 2 C27B C -0.2122(6) 0.5679(6) 0.2969(7) 0.080(3) Uani 0.35 1 d PG A 2 H27B H -0.2908 0.6187 0.3032 0.096 Uiso 0.35 1 calc PR A 2 C28B C -0.0791(7) 0.5548(8) 0.3372(7) 0.0450(7) Uani 0.35 1 d PGD A 2 C29B C 0.0359(5) 0.4804(6) 0.3280(5) 0.064(2) Uani 0.35 1 d PG A 2 H29B H 0.1268 0.4714 0.3555 0.077 Uiso 0.35 1 calc PR A 2 C30B C 0.0178(5) 0.4191(5) 0.2785(5) 0.059(2) Uani 0.35 1 d PG A 2 H30B H 0.0963 0.3683 0.2723 0.071 Uiso 0.35 1 calc PR A 2 C31B C -0.058(3) 0.6274(19) 0.3849(17) 0.068(7) Uani 0.35 1 d PD A 2 H31D H 0.0073 0.6826 0.3450 0.081 Uiso 0.35 1 calc PR A 2 H31E H -0.0135 0.5828 0.4450 0.081 Uiso 0.35 1 calc PR A 2 H31F H -0.1539 0.6638 0.3958 0.081 Uiso 0.35 1 calc PR A 2 O1S O 0.4234(2) 0.49134(17) 0.25343(19) 0.0891(7) Uani 1 1 d . . . C1S C 0.4249(4) 0.4806(3) 0.1653(3) 0.0950(11) Uani 1 1 d . . . H1SA H 0.3251 0.4687 0.1554 0.114 Uiso 1 1 calc R . . H1SB H 0.4942 0.4167 0.1671 0.114 Uiso 1 1 calc R . . C2S C 0.4716(7) 0.5817(4) 0.0873(3) 0.140(2) Uani 1 1 d . . . H2SA H 0.4729 0.5745 0.0279 0.168 Uiso 1 1 calc R . . H2SB H 0.5708 0.5928 0.0972 0.168 Uiso 1 1 calc R . . H2SC H 0.4021 0.6446 0.0854 0.168 Uiso 1 1 calc R . . C3S C 0.4011(5) 0.3968(3) 0.3303(4) 0.1156(15) Uani 1 1 d . . . H3SA H 0.4798 0.3381 0.3314 0.139 Uiso 1 1 calc R . . H3SB H 0.3046 0.3728 0.3286 0.139 Uiso 1 1 calc R . . C4S C 0.4038(6) 0.4195(4) 0.4168(3) 0.138(2) Uani 1 1 d . . . H4SA H 0.3829 0.3538 0.4730 0.166 Uiso 1 1 calc R . . H4SB H 0.3287 0.4800 0.4135 0.166 Uiso 1 1 calc R . . H4SC H 0.5015 0.4392 0.4196 0.166 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 Br 0.04102(12) 0.04140(12) 0.04736(12) -0.02159(9) 0.00004(8) -0.00149(8) Cl1 0.0315(2) 0.0624(3) 0.0400(2) -0.0246(2) -0.01018(18) 0.0054(2) Cl2 0.0309(2) 0.0639(3) 0.0638(3) -0.0445(3) -0.0010(2) -0.0080(2) S 0.0333(2) 0.0286(2) 0.0355(2) -0.01127(18) -0.00229(17) -0.00326(17) O1 0.0312(7) 0.0462(8) 0.0475(8) -0.0287(7) 0.0103(6) -0.0108(6) O2 0.0581(9) 0.0621(10) 0.0310(7) -0.0228(7) 0.0122(6) -0.0119(7) O3 0.0286(6) 0.0380(7) 0.0343(7) -0.0176(6) 0.0022(5) -0.0091(6) O4 0.0391(7) 0.0735(10) 0.0340(7) -0.0257(7) -0.0014(6) -0.0141(7) O5 0.0323(6) 0.0335(6) 0.0442(7) -0.0181(6) -0.0001(5) -0.0052(5) O6 0.0521(9) 0.0394(8) 0.0418(8) -0.0051(6) -0.0097(6) -0.0029(6) N1 0.0234(7) 0.0404(8) 0.0306(7) -0.0208(6) 0.0026(5) -0.0035(6) N2 0.0334(7) 0.0307(7) 0.0288(7) -0.0109(6) 0.0046(6) -0.0052(6) C1 0.0279(8) 0.0402(9) 0.0229(8) -0.0176(7) 0.0054(6) -0.0064(7) C2 0.0299(8) 0.0397(9) 0.0258(8) -0.0172(7) 0.0045(6) -0.0041(7) C3 0.0250(8) 0.0494(11) 0.0262(8) -0.0192(8) 0.0008(6) -0.0009(7) C4 0.0264(8) 0.0503(11) 0.0319(9) -0.0256(8) 0.0028(7) -0.0064(7) C5 0.0280(8) 0.0302(8) 0.0251(8) -0.0140(7) 0.0014(6) -0.0055(6) C6 0.0276(8) 0.0379(9) 0.0291(8) -0.0177(7) 0.0036(6) -0.0071(7) C7 0.0363(10) 0.0497(11) 0.0326(9) -0.0168(8) 0.0115(7) -0.0136(8) C8 0.0440(11) 0.0406(10) 0.0313(9) -0.0094(8) 0.0086(8) -0.0139(8) C9 0.0258(8) 0.0432(10) 0.0312(9) -0.0216(8) 0.0031(6) -0.0045(7) C10 0.0301(9) 0.0569(12) 0.0369(10) -0.0299(9) -0.0070(7) 0.0029(8) C11 0.0402(10) 0.0598(13) 0.0308(9) -0.0248(9) -0.0061(8) 0.0072(9) C12 0.0619(14) 0.0755(16) 0.0330(10) -0.0318(11) -0.0051(9) 0.0098(12) C13 0.0753(17) 0.0847(19) 0.0462(13) -0.0474(14) -0.0157(12) 0.0142(14) C14 0.0693(16) 0.0836(19) 0.0698(17) -0.0571(16) -0.0145(13) -0.0048(14) C15 0.0457(12) 0.0756(16) 0.0576(13) -0.0464(13) -0.0030(10) -0.0101(11) C16 0.092(2) 0.0790(19) 0.0385(12) -0.0243(13) 0.0262(13) -0.0221(16) C17 0.0265(8) 0.0307(8) 0.0261(8) -0.0143(7) 0.0026(6) -0.0055(6) C18 0.0373(9) 0.0289(8) 0.0244(8) -0.0117(7) 0.0054(7) -0.0054(7) C19 0.0456(10) 0.0390(10) 0.0280(9) -0.0157(8) 0.0044(7) -0.0119(8) C20 0.0743(15) 0.0510(12) 0.0310(10) -0.0220(9) 0.0052(10) -0.0230(11) C21 0.0863(17) 0.0511(13) 0.0310(10) -0.0246(10) 0.0150(11) -0.0094(12) C22 0.0600(14) 0.0649(15) 0.0390(11) -0.0243(11) 0.0186(10) 0.0025(11) C23 0.0429(11) 0.0546(12) 0.0335(10) -0.0198(9) 0.0067(8) -0.0023(9) C24 0.0544(14) 0.103(2) 0.0397(12) -0.0214(13) -0.0081(10) -0.0294(14) C25A 0.0323(10) 0.0281(9) 0.0465(13) -0.0177(9) 0.0001(10) -0.0021(8) C26A 0.074(3) 0.072(3) 0.073(3) -0.049(2) 0.034(2) -0.045(2) C27A 0.097(4) 0.078(3) 0.073(3) -0.055(3) 0.043(3) -0.046(3) C28A 0.0553(16) 0.0300(10) 0.0520(17) -0.0185(11) 0.0006(14) -0.0088(11) C29A 0.0435(19) 0.068(3) 0.103(3) -0.060(3) 0.013(2) -0.0197(18) C30A 0.0432(19) 0.071(3) 0.089(3) -0.058(3) 0.0225(19) -0.0225(18) C31A 0.076(5) 0.042(5) 0.061(5) -0.026(4) 0.007(4) -0.014(4) C25B 0.0323(10) 0.0281(9) 0.0465(13) -0.0177(9) 0.0001(10) -0.0021(8) C26B 0.043(4) 0.091(6) 0.141(9) -0.091(7) -0.035(5) 0.026(4) C27B 0.051(4) 0.081(6) 0.149(10) -0.090(7) -0.023(5) 0.019(4) C28B 0.0553(16) 0.0300(10) 0.0520(17) -0.0185(11) 0.0006(14) -0.0088(11) C29B 0.056(4) 0.071(5) 0.092(6) -0.059(5) -0.027(4) 0.010(4) C30B 0.045(4) 0.064(4) 0.095(6) -0.063(5) -0.019(4) 0.017(3) C31B 0.091(12) 0.041(9) 0.094(15) -0.045(10) -0.033(10) -0.001(7) O1S 0.0753(14) 0.0567(12) 0.125(2) -0.0320(13) 0.0112(13) -0.0050(10) C1S 0.071(2) 0.098(3) 0.138(3) -0.077(3) 0.003(2) 0.0036(18) C2S 0.200(6) 0.092(3) 0.106(3) -0.039(3) 0.001(3) 0.045(3) C3S 0.106(3) 0.069(2) 0.144(4) -0.025(2) 0.030(3) -0.014(2) C4S 0.180(5) 0.080(3) 0.106(3) -0.006(2) 0.042(3) -0.002(3) _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 Br C2 1.8680(18) . ? Cl1 C3 1.7167(18) . ? Cl2 C4 1.7048(19) . ? S O6 1.4257(15) . ? S O5 1.4281(13) . ? S N2 1.6678(15) . ? S C25A 1.739(3) . ? S C25B 1.787(3) . ? O1 C9 1.424(2) . ? O2 C11 1.363(3) . ? O2 C16 1.424(3) . ? O3 C17 1.431(2) . ? O4 C19 1.364(2) . ? O4 C24 1.433(3) . ? N1 C4 1.374(2) . ? N1 C1 1.391(2) . ? N1 C6 1.415(2) . ? N2 C8 1.401(2) . ? N2 C5 1.404(2) . ? C1 C2 1.369(3) . ? C1 C9 1.510(2) . ? C2 C3 1.414(2) . ? C3 C4 1.356(3) . ? C5 C6 1.365(2) . ? C5 C17 1.506(2) . ? C6 C7 1.415(3) . ? C7 C8 1.343(3) . ? C9 C10 1.517(2) . ? C10 C15 1.379(3) . ? C10 C11 1.395(3) . ? C11 C12 1.394(3) . ? C12 C13 1.369(4) . ? C13 C14 1.372(4) . ? C14 C15 1.397(3) . ? C17 C18 1.523(2) . ? C18 C23 1.382(3) . ? C18 C19 1.395(3) . ? C19 C20 1.398(3) . ? C20 C21 1.373(4) . ? C21 C22 1.368(4) . ? C22 C23 1.395(3) . ? C25A C26A 1.348(6) . ? C25A C30A 1.353(7) . ? C26A C27A 1.391(5) . ? C27A C28A 1.368(7) . ? C28A C29A 1.378(7) . ? C28A C31A 1.506(5) . ? C29A C30A 1.377(5) . ? C25B C26B 1.3900 . ? C25B C30B 1.3900 . ? C26B C27B 1.3900 . ? C27B C28B 1.3900 . ? C28B C29B 1.3900 . ? C28B C31B 1.508(6) . ? C29B C30B 1.3900 . ? O1S C3S 1.364(4) . ? O1S C1S 1.453(4) . ? C1S C2S 1.484(6) . ? C3S C4S 1.520(7) . ? 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 O6 S O5 119.15(9) . . ? O6 S N2 105.26(9) . . ? O5 S N2 106.56(8) . . ? O6 S C25A 108.5(2) . . ? O5 S C25A 111.9(2) . . ? N2 S C25A 104.30(13) . . ? O6 S C25B 109.9(4) . . ? O5 S C25B 107.9(4) . . ? N2 S C25B 107.39(16) . . ? C11 O2 C16 117.49(18) . . ? C19 O4 C24 116.86(17) . . ? C4 N1 C1 109.04(15) . . ? C4 N1 C6 124.56(15) . . ? C1 N1 C6 126.26(14) . . ? C8 N2 C5 109.20(15) . . ? C8 N2 S 120.81(13) . . ? C5 N2 S 129.76(12) . . ? C2 C1 N1 106.54(15) . . ? C2 C1 C9 132.25(16) . . ? N1 C1 C9 121.10(15) . . ? C1 C2 C3 108.65(16) . . ? C1 C2 Br 127.43(14) . . ? C3 C2 Br 123.91(14) . . ? C4 C3 C2 107.17(16) . . ? C4 C3 Cl1 126.03(14) . . ? C2 C3 Cl1 126.77(15) . . ? C3 C4 N1 108.56(16) . . ? C3 C4 Cl2 130.09(14) . . ? N1 C4 Cl2 121.23(15) . . ? C6 C5 N2 105.09(14) . . ? C6 C5 C17 126.36(16) . . ? N2 C5 C17 128.53(14) . . ? C5 C6 N1 124.72(15) . . ? C5 C6 C7 110.31(16) . . ? N1 C6 C7 124.94(16) . . ? C8 C7 C6 107.19(16) . . ? C7 C8 N2 108.18(17) . . ? O1 C9 C1 111.24(14) . . ? O1 C9 C10 109.43(15) . . ? C1 C9 C10 111.21(14) . . ? C15 C10 C11 119.00(18) . . ? C15 C10 C9 122.09(18) . . ? C11 C10 C9 118.90(18) . . ? O2 C11 C12 124.0(2) . . ? O2 C11 C10 115.55(16) . . ? C12 C11 C10 120.4(2) . . ? C13 C12 C11 119.4(2) . . ? C12 C13 C14 121.2(2) . . ? C13 C14 C15 119.6(2) . . ? C10 C15 C14 120.4(2) . . ? O3 C17 C5 111.80(13) . . ? O3 C17 C18 112.05(13) . . ? C5 C17 C18 116.94(14) . . ? C23 C18 C19 118.13(17) . . ? C23 C18 C17 122.71(17) . . ? C19 C18 C17 118.84(15) . . ? O4 C19 C18 115.80(15) . . ? O4 C19 C20 123.72(19) . . ? C18 C19 C20 120.48(19) . . ? C21 C20 C19 119.9(2) . . ? C22 C21 C20 120.50(19) . . ? C21 C22 C23 119.7(2) . . ? C18 C23 C22 121.2(2) . . ? C26A C25A C30A 122.3(3) . . ? C26A C25A S 118.1(4) . . ? C30A C25A S 119.4(4) . . ? C25A C26A C27A 117.9(3) . . ? C28A C27A C26A 122.6(4) . . ? C27A C28A C29A 116.4(3) . . ? C27A C28A C31A 120.5(7) . . ? C29A C28A C31A 123.1(7) . . ? C30A C29A C28A 122.3(4) . . ? C25A C30A C29A 118.5(4) . . ? C26B C25B C30B 120.0 . . ? C26B C25B S 118.9(3) . . ? C30B C25B S 121.0(3) . . ? C27B C26B C25B 120.0 . . ? C26B C27B C28B 120.0 . . ? C27B C28B C29B 120.0 . . ? C27B C28B C31B 119.2(12) . . ? C29B C28B C31B 120.7(12) . . ? C30B C29B C28B 120.0 . . ? C29B C30B C25B 120.0 . . ? C3S O1S C1S 113.5(3) . . ? O1S C1S C2S 109.4(3) . . ? O1S C3S C4S 107.8(4) . . ? 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 O6 S N2 C8 22.96(17) . . . . ? O5 S N2 C8 150.39(15) . . . . ? C25A S N2 C8 -91.2(3) . . . . ? C25B S N2 C8 -94.2(4) . . . . ? O6 S N2 C5 -150.78(15) . . . . ? O5 S N2 C5 -23.35(18) . . . . ? C25A S N2 C5 95.1(3) . . . . ? C25B S N2 C5 92.1(4) . . . . ? C4 N1 C1 C2 1.66(18) . . . . ? C6 N1 C1 C2 177.54(15) . . . . ? C4 N1 C1 C9 -174.97(14) . . . . ? C6 N1 C1 C9 0.9(2) . . . . ? N1 C1 C2 C3 -0.82(18) . . . . ? C9 C1 C2 C3 175.28(17) . . . . ? N1 C1 C2 Br -179.90(12) . . . . ? C9 C1 C2 Br -3.8(3) . . . . ? C1 C2 C3 C4 -0.31(19) . . . . ? Br C2 C3 C4 178.81(12) . . . . ? C1 C2 C3 Cl1 -178.57(13) . . . . ? Br C2 C3 Cl1 0.5(2) . . . . ? C2 C3 C4 N1 1.34(19) . . . . ? Cl1 C3 C4 N1 179.62(12) . . . . ? C2 C3 C4 Cl2 -174.70(14) . . . . ? Cl1 C3 C4 Cl2 3.6(3) . . . . ? C1 N1 C4 C3 -1.89(19) . . . . ? C6 N1 C4 C3 -177.86(15) . . . . ? C1 N1 C4 Cl2 174.57(12) . . . . ? C6 N1 C4 Cl2 -1.4(2) . . . . ? C8 N2 C5 C6 -1.77(19) . . . . ? S N2 C5 C6 172.54(13) . . . . ? C8 N2 C5 C17 -179.89(16) . . . . ? S N2 C5 C17 -5.6(3) . . . . ? N2 C5 C6 N1 -176.30(15) . . . . ? C17 C5 C6 N1 1.9(3) . . . . ? N2 C5 C6 C7 2.08(19) . . . . ? C17 C5 C6 C7 -179.74(16) . . . . ? C4 N1 C6 C5 -113.0(2) . . . . ? C1 N1 C6 C5 71.7(2) . . . . ? C4 N1 C6 C7 68.8(2) . . . . ? C1 N1 C6 C7 -106.4(2) . . . . ? C5 C6 C7 C8 -1.7(2) . . . . ? N1 C6 C7 C8 176.72(17) . . . . ? C6 C7 C8 N2 0.5(2) . . . . ? C5 N2 C8 C7 0.8(2) . . . . ? S N2 C8 C7 -174.11(14) . . . . ? C2 C1 C9 O1 74.1(2) . . . . ? N1 C1 C9 O1 -110.23(17) . . . . ? C2 C1 C9 C10 -48.1(3) . . . . ? N1 C1 C9 C10 127.51(17) . . . . ? O1 C9 C10 C15 -4.0(3) . . . . ? C1 C9 C10 C15 119.3(2) . . . . ? O1 C9 C10 C11 174.60(17) . . . . ? C1 C9 C10 C11 -62.1(2) . . . . ? C16 O2 C11 C12 9.6(3) . . . . ? C16 O2 C11 C10 -171.1(2) . . . . ? C15 C10 C11 O2 177.44(19) . . . . ? C9 C10 C11 O2 -1.2(3) . . . . ? C15 C10 C11 C12 -3.2(3) . . . . ? C9 C10 C11 C12 178.12(19) . . . . ? O2 C11 C12 C13 -179.4(2) . . . . ? C10 C11 C12 C13 1.3(3) . . . . ? C11 C12 C13 C14 1.4(4) . . . . ? C12 C13 C14 C15 -2.2(4) . . . . ? C11 C10 C15 C14 2.4(3) . . . . ? C9 C10 C15 C14 -179.0(2) . . . . ? C13 C14 C15 C10 0.3(4) . . . . ? C6 C5 C17 O3 -101.98(19) . . . . ? N2 C5 C17 O3 75.8(2) . . . . ? C6 C5 C17 C18 126.96(18) . . . . ? N2 C5 C17 C18 -55.3(2) . . . . ? O3 C17 C18 C23 -12.8(2) . . . . ? C5 C17 C18 C23 118.14(19) . . . . ? O3 C17 C18 C19 160.59(16) . . . . ? C5 C17 C18 C19 -68.5(2) . . . . ? C24 O4 C19 C18 -165.6(2) . . . . ? C24 O4 C19 C20 13.1(3) . . . . ? C23 C18 C19 O4 175.72(18) . . . . ? C17 C18 C19 O4 2.0(2) . . . . ? C23 C18 C19 C20 -3.0(3) . . . . ? C17 C18 C19 C20 -176.70(17) . . . . ? O4 C19 C20 C21 -177.0(2) . . . . ? C18 C19 C20 C21 1.6(3) . . . . ? C19 C20 C21 C22 0.7(4) . . . . ? C20 C21 C22 C23 -1.5(4) . . . . ? C19 C18 C23 C22 2.2(3) . . . . ? C17 C18 C23 C22 175.65(19) . . . . ? C21 C22 C23 C18 0.0(4) . . . . ? O6 S C25A C26A 120.3(5) . . . . ? O5 S C25A C26A -13.1(5) . . . . ? N2 S C25A C26A -127.9(4) . . . . ? O6 S C25A C30A -54.1(4) . . . . ? O5 S C25A C30A 172.5(4) . . . . ? N2 S C25A C30A 57.7(5) . . . . ? C30A C25A C26A C27A -1.3(9) . . . . ? S C25A C26A C27A -175.6(4) . . . . ? C25A C26A C27A C28A -0.7(10) . . . . ? C26A C27A C28A C29A 0.8(10) . . . . ? C26A C27A C28A C31A -179.0(8) . . . . ? C27A C28A C29A C30A 1.0(9) . . . . ? C31A C28A C29A C30A -179.1(8) . . . . ? C26A C25A C30A C29A 3.1(9) . . . . ? S C25A C30A C29A 177.3(4) . . . . ? C28A C29A C30A C25A -3.0(9) . . . . ? O6 S C25B C26B 62.7(6) . . . . ? O5 S C25B C26B -68.7(5) . . . . ? N2 S C25B C26B 176.7(4) . . . . ? O6 S C25B C30B -113.6(5) . . . . ? O5 S C25B C30B 114.9(5) . . . . ? N2 S C25B C30B 0.4(7) . . . . ? C30B C25B C26B C27B 0.0 . . . . ? S C25B C26B C27B -176.4(9) . . . . ? C25B C26B C27B C28B 0.0 . . . . ? C26B C27B C28B C29B 0.0 . . . . ? C26B C27B C28B C31B 175.9(15) . . . . ? C27B C28B C29B C30B 0.0 . . . . ? C31B C28B C29B C30B -175.8(16) . . . . ? C28B C29B C30B C25B 0.0 . . . . ? C26B C25B C30B C29B 0.0 . . . . ? S C25B C30B C29B 176.3(9) . . . . ? C3S O1S C1S C2S -171.6(4) . . . . ? C1S O1S C3S C4S 179.4(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 O1 H1O O3 0.75(3) 2.06(3) 2.794(2) 168(3) . O3 H3O O5 0.77(3) 2.21(3) 2.876(2) 146(3) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.449 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.049 #===END