# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 3-Bromo-4-(methoxycarbonyl)-2-(2-nitroethyl)pyrrole ; _chemical_name_common VA_23 _chemical_formula_moiety ? _chemical_formula_sum 'C8 H9 Br N2 O4' _chemical_formula_iupac ? _chemical_formula_weight 277.08 _chemical_melting_point 423 #=============================================================================== # 6. CRYSTAL DATA _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3702(2) _cell_length_b 7.6424(3) _cell_length_c 9.3429(3) _cell_angle_alpha 95.852(2) _cell_angle_beta 105.3520(10) _cell_angle_gamma 93.7530(10) _cell_volume 502.48(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8374 _cell_measurement_theta_min 2.6917 _cell_measurement_theta_max 31.6820 _cell_measurement_temperature 100.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.250 _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 4.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.5915 _exptl_absorpt_correction_T_max 0.7463 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'fine-focus sealed tube' _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8 Kappa APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 9158 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _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. ; _reflns_number_total 2021 _reflns_number_gt 1968 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0216 _refine_ls_wR_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.0612 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_number_reflns 2021 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.3139P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.906 _refine_diff_density_min -0.293 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Br Br -0.2901 2.4595 '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' _computing_data_collection 'Bruker Instrument Service v2009, 11, 0, 0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS Inc., 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS Inc., 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.5097(3) 0.3020(2) 0.8838(2) 0.0144(4) Uani d . 1 . . C C2 0.3256(3) 0.2903(2) 0.8891(2) 0.0139(4) Uani d . 1 . . C C3 0.3167(3) 0.2277(2) 1.0260(2) 0.0135(4) Uani d . 1 . . C C4 0.5012(3) 0.2024(3) 1.0995(2) 0.0151(4) Uani d . 1 . . H H4 0.5416 0.1615 1.1945 0.018 Uiso calc R 1 . . C C5 0.5985(3) 0.3619(3) 0.7684(2) 0.0168(4) Uani d . 1 . . H H5A 0.7299 0.4136 0.817 0.02 Uiso calc R 1 . . H H5B 0.527 0.4543 0.7183 0.02 Uiso calc R 1 . . C C6 0.5988(3) 0.2074(3) 0.6540(2) 0.0217(4) Uani d . 1 . . H H6A 0.6703 0.1157 0.7052 0.026 Uiso calc R 1 . . H H6B 0.4671 0.1553 0.6074 0.026 Uiso calc R 1 . . C C7 0.1527(3) 0.2048(2) 1.0834(2) 0.0146(4) Uani d . 1 . . C C8 0.0444(3) 0.1499(3) 1.2928(2) 0.0219(4) Uani d . 1 . . H H8A -0.0501 0.0553 1.2339 0.033 Uiso calc R 1 . . H H8B -0.0137 0.2615 1.295 0.033 Uiso calc R 1 . . H H8C 0.0921 0.1212 1.3951 0.033 Uiso calc R 1 . . N N1 0.6132(2) 0.2457(2) 1.01291(18) 0.0151(3) Uani d . 1 . . H H1 0.7361 0.2387 1.0361 0.018 Uiso calc R 1 . . Br Br1 0.12878(2) 0.35731(2) 0.73883(2) 0.01841(9) Uani d . 1 . . N N2 0.6848(2) 0.2588(2) 0.53385(19) 0.0190(4) Uani d . 1 . . O O1 0.7169(3) 0.4142(2) 0.52305(19) 0.0303(4) Uani d . 1 . . O O2 0.7192(2) 0.1363(2) 0.45136(16) 0.0257(3) Uani d . 1 . . O O3 -0.0086(2) 0.2198(2) 1.01395(17) 0.0206(3) Uani d . 1 . . O O4 0.19976(19) 0.16719(19) 1.22522(16) 0.0188(3) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0131(9) 0.0161(9) 0.0143(9) 0.0019(7) 0.0045(7) 0.0009(7) C2 0.0118(8) 0.0156(9) 0.0136(9) 0.0018(7) 0.0025(7) 0.0016(7) C3 0.0120(9) 0.0153(9) 0.0134(9) 0.0022(7) 0.0042(7) 0.0010(7) C4 0.0120(8) 0.0199(9) 0.0135(9) 0.0026(7) 0.0037(7) 0.0017(7) C5 0.0159(9) 0.0166(9) 0.0200(9) 0.0001(7) 0.0084(8) 0.0038(7) C6 0.0280(11) 0.0217(10) 0.0195(10) -0.0025(8) 0.0149(8) 0.0023(8) C7 0.0139(9) 0.0145(9) 0.0164(9) 0.0028(7) 0.0055(7) 0.0019(7) C8 0.0208(10) 0.0290(11) 0.0224(10) 0.0058(8) 0.0145(8) 0.0088(8) N1 0.0093(7) 0.0205(8) 0.0157(8) 0.0021(6) 0.0039(6) 0.0018(6) Br1 0.01316(12) 0.02335(13) 0.01820(13) 0.00205(8) 0.00127(8) 0.00803(8) N2 0.0138(8) 0.0302(10) 0.0130(8) 0.0003(7) 0.0029(6) 0.0053(7) O1 0.0384(9) 0.0299(9) 0.0287(9) 0.0037(7) 0.0155(7) 0.0150(7) O2 0.0241(8) 0.0372(9) 0.0159(7) 0.0002(6) 0.0087(6) -0.0023(6) O3 0.0121(7) 0.0307(8) 0.0223(7) 0.0047(6) 0.0078(6) 0.0088(6) O4 0.0152(7) 0.0279(8) 0.0174(7) 0.0044(5) 0.0092(5) 0.0071(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.368(3) ? C1 N1 . 1.373(2) ? C1 C5 . 1.495(3) ? C2 C3 . 1.426(3) ? C2 Br1 . 1.8722(19) ? C3 C4 . 1.388(3) ? C3 C7 . 1.454(2) ? C4 N1 . 1.348(2) ? C5 C6 . 1.510(3) ? C6 N2 . 1.500(2) ? C7 O3 . 1.213(2) ? C7 O4 . 1.344(2) ? C8 O4 . 1.452(2) ? N2 O1 . 1.216(2) ? N2 O2 . 1.233(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 N1 . . 106.50(16) ? C2 C1 C5 . . 131.19(18) ? N1 C1 C5 . . 122.31(17) ? C1 C2 C3 . . 108.79(16) ? C1 C2 Br1 . . 122.81(15) ? C3 C2 Br1 . . 128.36(14) ? C4 C3 C2 . . 105.62(16) ? C4 C3 C7 . . 126.20(17) ? C2 C3 C7 . . 128.08(17) ? N1 C4 C3 . . 108.28(17) ? C1 C5 C6 . . 109.90(16) ? N2 C6 C5 . . 112.68(16) ? O3 C7 O4 . . 122.99(17) ? O3 C7 C3 . . 124.82(18) ? O4 C7 C3 . . 112.18(16) ? C4 N1 C1 . . 110.80(15) ? O1 N2 O2 . . 124.10(17) ? O1 N2 C6 . . 119.64(17) ? O2 N2 C6 . . 116.26(17) ? C7 O4 C8 . . 115.47(15) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O3 1_655 0.88 1.96 2.805(2) 160.5 ? _database_code_depnum_ccdc_archive 'CCDC 958396' ####################################################################### # # 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_I #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 3-Bromo-2-(2-nitroethyl)-N-tosylpyrrole ; _chemical_name_common VAA-48 _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Br N2 O4 S' _chemical_formula_iupac ? _chemical_formula_weight 373.22 _chemical_absolute_configuration ad _chemical_melting_point 407 #=============================================================================== # 6. CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.5461(4) _cell_length_b 9.6709(4) _cell_length_c 15.4442(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1425.80(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9874 _cell_measurement_theta_min 2.4849 _cell_measurement_theta_max 33.2199 _cell_measurement_temperature 110.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.240 _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 3.046 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.53 _exptl_special_details ; ; _diffrn_ambient_temperature 110.(2) _diffrn_source 'fine-focus sealed tube' _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8 Kappa APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 43538 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 33.29 _diffrn_reflns_theta_full 33.29 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _refine_special_details 'Refined as a 2-component inversion twin.' _reflns_number_total 5415 _reflns_number_gt 5009 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0192 _refine_ls_wR_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.0491 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_number_reflns 5415 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0275P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.390 _refine_diff_density_min -0.505 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Refined as an inversion twin.' _refine_ls_abs_structure_Flack 0.007(5) 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' _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS Inc., 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS Inc., 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.75029(2) 0.21626(2) 1.18906(2) 0.01715(4) Uani d . . . 1 . . S S1 0.73962(4) 0.59505(4) 0.91628(2) 0.01507(7) Uani d . . . 1 . . O O1 1.23505(15) 0.50232(15) 1.15936(8) 0.0266(3) Uani d . . . 1 . . O O2 0.62098(13) 0.68208(12) 0.90044(8) 0.0212(3) Uani d . . . 1 . . O O3 1.22125(13) 0.4341(2) 1.02720(9) 0.0374(4) Uani d . . . 1 . . O O4 0.87466(13) 0.65327(13) 0.93076(8) 0.0200(2) Uani d . . . 1 . . N N1 1.16857(14) 0.47442(15) 1.09410(10) 0.0188(3) Uani d . . . 1 . . N N2 0.69604(14) 0.50568(15) 1.00546(8) 0.0150(2) Uani d . . . 1 . . C C1 1.01368(16) 0.49464(17) 1.09750(10) 0.0172(3) Uani d . . . 1 . . H H1A 0.9913 0.5909 1.0807 0.021 Uiso calc U . R 1 . . H H1B 0.9809 0.4806 1.1577 0.021 Uiso calc U . R 1 . . C C2 0.93596(15) 0.39552(16) 1.03785(10) 0.0140(3) Uani d . . . 1 . . H H2A 0.961 0.4152 0.9769 0.017 Uiso calc U . R 1 . . H H2B 0.9638 0.2992 1.0511 0.017 Uiso calc U . R 1 . . C C3 0.78124(14) 0.41159(16) 1.04990(9) 0.0134(3) Uani d . . . 1 . . C C4 0.7514(2) 0.46791(14) 0.83586(9) 0.0149(2) Uani d . . . 1 . . C C5 0.62975(16) 0.39552(18) 0.81387(11) 0.0175(3) Uani d . . . 1 . . H H5 0.5442 0.4126 0.8434 0.021 Uiso calc U . R 1 . . C C6 0.63643(18) 0.29821(18) 0.74807(11) 0.0185(3) Uani d . . . 1 . . H H6 0.5547 0.2477 0.7327 0.022 Uiso calc U . R 1 . . C C7 0.76218(17) 0.27339(15) 0.70392(10) 0.0173(3) Uani d . . . 1 . . C C8 0.7658(2) 0.17144(18) 0.63051(10) 0.0240(3) Uani d . . . 1 . . H H8A 0.8575 0.1754 0.602 0.036 Uiso calc U . R 1 . . H H8B 0.6924 0.1944 0.5886 0.036 Uiso calc U . R 1 . . H H8C 0.75 0.078 0.6531 0.036 Uiso calc U . R 1 . . C C9 0.87748(17) 0.44272(18) 0.79426(11) 0.0180(3) Uani d . . . 1 . . H H9 0.9597 0.4915 0.8105 0.022 Uiso calc U . R 1 . . C C10 0.88163(17) 0.34492(19) 0.72835(11) 0.0190(3) Uani d . . . 1 . . H H10 0.9677 0.3268 0.6996 0.023 Uiso calc U . R 1 . . C C11 0.55713(16) 0.48985(18) 1.03196(11) 0.0167(3) Uani d . . . 1 . . H H11 0.4788 0.5392 1.0099 0.02 Uiso calc U . R 1 . . C C12 0.55364(15) 0.39217(17) 1.09435(10) 0.0166(3) Uani d . . . 1 . . H H12 0.4732 0.3609 1.1248 0.02 Uiso calc U . R 1 . . C C13 0.69331(16) 0.34508(16) 1.10578(10) 0.0139(3) Uani d . . . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.01604(7) 0.01658(7) 0.01882(7) 0.00145(7) -0.00068(7) 0.00380(5) S1 0.01468(16) 0.01388(15) 0.01667(15) 0.00070(15) 0.00006(15) 0.00203(11) O1 0.0187(7) 0.0333(7) 0.0280(6) 0.0009(5) -0.0096(5) -0.0079(5) O2 0.0218(6) 0.0175(6) 0.0243(6) 0.0070(4) -0.0001(5) 0.0048(5) O3 0.0139(6) 0.0687(11) 0.0295(7) 0.0008(6) 0.0048(5) -0.0131(7) O4 0.0187(5) 0.0179(6) 0.0234(6) -0.0050(5) 0.0008(5) 0.0018(5) N1 0.0134(6) 0.0194(7) 0.0235(7) -0.0016(5) -0.0021(5) -0.0002(6) N2 0.0128(5) 0.0171(6) 0.0149(6) 0.0017(5) 0.0004(4) 0.0016(5) C1 0.0104(6) 0.0198(7) 0.0215(8) 0.0001(5) -0.0008(5) -0.0036(6) C2 0.0111(6) 0.0148(7) 0.0161(7) 0.0016(5) -0.0005(5) -0.0014(6) C3 0.0109(6) 0.0134(6) 0.0159(7) 0.0012(4) -0.0012(4) -0.0019(5) C4 0.0146(6) 0.0153(6) 0.0148(5) -0.0003(7) -0.0008(7) 0.0027(5) C5 0.0135(6) 0.0210(7) 0.0179(7) -0.0011(6) 0.0010(6) 0.0027(7) C6 0.0180(7) 0.0184(7) 0.0192(8) -0.0019(6) -0.0030(6) 0.0019(6) C7 0.0206(7) 0.0143(6) 0.0169(6) 0.0031(6) -0.0021(6) 0.0035(5) C8 0.0299(10) 0.0189(7) 0.0231(7) 0.0030(7) -0.0003(7) -0.0022(6) C9 0.0137(7) 0.0215(8) 0.0187(8) 0.0002(6) 0.0005(6) 0.0020(6) C10 0.0170(7) 0.0206(8) 0.0194(8) 0.0031(6) 0.0017(6) 0.0036(7) C11 0.0113(6) 0.0213(8) 0.0176(7) 0.0024(5) -0.0002(5) -0.0005(6) C12 0.0113(6) 0.0193(7) 0.0192(7) -0.0001(5) 0.0013(5) -0.0009(6) C13 0.0131(6) 0.0135(6) 0.0151(7) 0.0006(5) -0.0018(5) 0.0003(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C13 . 1.8714(15) ? S1 O4 . 1.4244(13) ? S1 O2 . 1.4321(13) ? S1 N2 . 1.6783(14) ? S1 C4 . 1.7514(14) ? O1 N1 . 1.2213(18) ? O3 N1 . 1.2136(19) ? N1 C1 . 1.492(2) ? N2 C11 . 1.396(2) ? N2 C3 . 1.4002(19) ? C1 C2 . 1.523(2) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 C3 . 1.4968(19) ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 C13 . 1.365(2) ? C4 C9 . 1.386(2) ? C4 C5 . 1.398(2) ? C5 C6 . 1.386(2) ? C5 H5 . 0.95 ? C6 C7 . 1.401(2) ? C6 H6 . 0.95 ? C7 C10 . 1.386(2) ? C7 C8 . 1.503(2) ? C8 H8A . 0.98 ? C8 H8B . 0.98 ? C8 H8C . 0.98 ? C9 C10 . 1.390(2) ? C9 H9 . 0.95 ? C10 H10 . 0.95 ? C11 C12 . 1.350(2) ? C11 H11 . 0.95 ? C12 C13 . 1.420(2) ? C12 H12 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 S1 O2 . . 120.68(8) ? O4 S1 N2 . . 107.40(7) ? O2 S1 N2 . . 104.29(7) ? O4 S1 C4 . . 109.32(8) ? O2 S1 C4 . . 110.00(8) ? N2 S1 C4 . . 103.67(7) ? O3 N1 O1 . . 123.94(15) ? O3 N1 C1 . . 118.86(14) ? O1 N1 C1 . . 117.19(15) ? C11 N2 C3 . . 109.68(13) ? C11 N2 S1 . . 122.17(11) ? C3 N2 S1 . . 126.37(11) ? N1 C1 C2 . . 112.27(13) ? N1 C1 H1A . . 109.2 ? C2 C1 H1A . . 109.2 ? N1 C1 H1B . . 109.2 ? C2 C1 H1B . . 109.2 ? H1A C1 H1B . . 107.9 ? C3 C2 C1 . . 109.89(13) ? C3 C2 H2A . . 109.7 ? C1 C2 H2A . . 109.7 ? C3 C2 H2B . . 109.7 ? C1 C2 H2B . . 109.7 ? H2A C2 H2B . . 108.2 ? C13 C3 N2 . . 105.01(13) ? C13 C3 C2 . . 129.53(14) ? N2 C3 C2 . . 125.43(14) ? C9 C4 C5 . . 121.38(14) ? C9 C4 S1 . . 120.52(14) ? C5 C4 S1 . . 118.08(14) ? C6 C5 C4 . . 118.68(15) ? C6 C5 H5 . . 120.7 ? C4 C5 H5 . . 120.7 ? C5 C6 C7 . . 120.82(15) ? C5 C6 H6 . . 119.6 ? C7 C6 H6 . . 119.6 ? C10 C7 C6 . . 119.13(14) ? C10 C7 C8 . . 120.91(15) ? C6 C7 C8 . . 119.96(15) ? C7 C8 H8A . . 109.5 ? C7 C8 H8B . . 109.5 ? H8A C8 H8B . . 109.5 ? C7 C8 H8C . . 109.5 ? H8A C8 H8C . . 109.5 ? H8B C8 H8C . . 109.5 ? C4 C9 C10 . . 118.93(15) ? C4 C9 H9 . . 120.5 ? C10 C9 H9 . . 120.5 ? C7 C10 C9 . . 121.02(15) ? C7 C10 H10 . . 119.5 ? C9 C10 H10 . . 119.5 ? C12 C11 N2 . . 108.02(13) ? C12 C11 H11 . . 126.0 ? N2 C11 H11 . . 126.0 ? C11 C12 C13 . . 106.87(14) ? C11 C12 H12 . . 126.6 ? C13 C12 H12 . . 126.6 ? C3 C13 C12 . . 110.34(14) ? C3 C13 Br1 . . 124.72(12) ? C12 C13 Br1 . . 124.88(12) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O4 S1 N2 C11 . . . . 149.74(13) ? O2 S1 N2 C11 . . . . 20.57(15) ? C4 S1 N2 C11 . . . . -94.60(15) ? O4 S1 N2 C3 . . . . -47.09(16) ? O2 S1 N2 C3 . . . . -176.27(13) ? C4 S1 N2 C3 . . . . 68.57(15) ? O3 N1 C1 C2 . . . . 30.5(2) ? O1 N1 C1 C2 . . . . -150.80(15) ? N1 C1 C2 C3 . . . . 174.87(13) ? C11 N2 C3 C13 . . . . -2.95(17) ? S1 N2 C3 C13 . . . . -167.86(12) ? C11 N2 C3 C2 . . . . 178.83(15) ? S1 N2 C3 C2 . . . . 13.9(2) ? C1 C2 C3 C13 . . . . -89.8(2) ? C1 C2 C3 N2 . . . . 88.00(18) ? O4 S1 C4 C9 . . . . -3.09(15) ? O2 S1 C4 C9 . . . . 131.58(13) ? N2 S1 C4 C9 . . . . -117.39(13) ? O4 S1 C4 C5 . . . . 178.30(12) ? O2 S1 C4 C5 . . . . -47.03(14) ? N2 S1 C4 C5 . . . . 64.00(13) ? C9 C4 C5 C6 . . . . -1.0(2) ? S1 C4 C5 C6 . . . . 177.63(12) ? C4 C5 C6 C7 . . . . -0.5(2) ? C5 C6 C7 C10 . . . . 1.7(3) ? C5 C6 C7 C8 . . . . -177.63(15) ? C5 C4 C9 C10 . . . . 1.1(2) ? S1 C4 C9 C10 . . . . -177.45(12) ? C6 C7 C10 C9 . . . . -1.6(3) ? C8 C7 C10 C9 . . . . 177.77(15) ? C4 C9 C10 C7 . . . . 0.2(2) ? C3 N2 C11 C12 . . . . 2.41(18) ? S1 N2 C11 C12 . . . . 168.07(12) ? N2 C11 C12 C13 . . . . -0.85(18) ? N2 C3 C13 C12 . . . . 2.42(18) ? C2 C3 C13 C12 . . . . -179.46(16) ? N2 C3 C13 Br1 . . . . -174.95(11) ? C2 C3 C13 Br1 . . . . 3.2(2) ? C11 C12 C13 C3 . . . . -1.03(19) ? C11 C12 C13 Br1 . . . . 176.34(12) ? _database_code_depnum_ccdc_archive 'CCDC 958397'