data_br1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 Br N2 O2 S2' _chemical_formula_weight 451.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6171(3) _cell_length_b 12.0557(4) _cell_length_c 15.7265(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.334(1) _cell_angle_gamma 90.00 _cell_volume 1910.76(12) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4255 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 2.386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.56 _exptl_absorpt_process_details ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8165 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4366 _reflns_number_gt 3645 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. The thiophene ring was disordered by rotation of the C-C bond to the remainder of the molecule. The rings are rotated by about 180 degrees relative to each other. The disorder was modeled by assigning the variable x to the site occupancy factors of one orientation of the ring and (1-x) to the site occupancy factors for the alternate conformation. The geometry of the two rings was restrained to be equal throughout the refinement process. The variable x refined to a value very close to 0.5. The site occupancy factors were then set to 1/2 for the remainder of the refinement. The atoms were refined anisotropically with their displacement parameters restrained to be approximately isotropic. ; _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^)+(0.0321P)^2^+1.1485P] 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 SHELXL _refine_ls_extinction_coef 0.0010(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4366 _refine_ls_number_parameters 280 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.007131(19) 0.455675(19) 0.334404(13) 0.03274(9) Uani 1 1 d . . . N1 N 0.26954(14) 0.39216(12) 0.39337(10) 0.0208(3) Uani 1 1 d . . . N2 N 0.44737(16) 0.13711(13) 0.40651(11) 0.0208(3) Uani 1 1 d . . . O1 O 0.24947(13) 0.06582(12) 0.29005(9) 0.0287(3) Uani 1 1 d . . . O2 O 0.37104(13) -0.04984(10) 0.42094(9) 0.0263(3) Uani 1 1 d . . . S1 S 0.32020(4) 0.05649(4) 0.38383(3) 0.02023(11) Uani 1 1 d . . . S2 S 0.6076(2) 0.0866(2) 0.28849(16) 0.0270(4) Uani 0.50 1 d PDU A 1 C17 C 0.7144(8) 0.1348(8) 0.2353(5) 0.0281(17) Uani 0.50 1 d PDU A 1 H17A H 0.7689 0.0887 0.2126 0.034 Uiso 0.50 1 calc PR A 1 C18 C 0.7115(8) 0.2466(8) 0.2298(6) 0.0294(17) Uani 0.50 1 d PDU A 1 H18A H 0.7642 0.2884 0.2025 0.035 Uiso 0.50 1 calc PR A 1 C19 C 0.6221(10) 0.2948(7) 0.2688(6) 0.034(3) Uani 0.50 1 d PDU A 1 H19A H 0.6079 0.3725 0.2705 0.041 Uiso 0.50 1 calc PR A 1 S2A S 0.6147(3) 0.3207(2) 0.25845(17) 0.0303(4) Uani 0.50 1 d PDU A 2 C17A C 0.7163(7) 0.2328(8) 0.2217(6) 0.0270(17) Uani 0.50 1 d PDU A 2 H17B H 0.7737 0.2560 0.1894 0.032 Uiso 0.50 1 calc PR A 2 C18A C 0.7025(9) 0.1254(8) 0.2456(6) 0.0312(16) Uani 0.50 1 d PDU A 2 H18B H 0.7497 0.0646 0.2319 0.037 Uiso 0.50 1 calc PR A 2 C19A C 0.6101(10) 0.1155(7) 0.2932(6) 0.036(3) Uani 0.50 1 d PDU A 2 H19B H 0.5877 0.0470 0.3147 0.044 Uiso 0.50 1 calc PR A 2 C1 C 0.45809(17) 0.23596(15) 0.35536(11) 0.0195(4) Uani 1 1 d . A . H1 H 0.3692 0.2502 0.3105 0.023 Uiso 1 1 calc R . . C2 C 0.49690(17) 0.33929(15) 0.41669(12) 0.0205(4) Uani 1 1 d . . . H2 H 0.5033 0.4031 0.3776 0.025 Uiso 1 1 calc R . . C3 C 0.38735(18) 0.36638(14) 0.45544(12) 0.0201(4) Uani 1 1 d . . . C4 C 0.40249(19) 0.36665(16) 0.54646(12) 0.0255(4) Uani 1 1 d . . . H4 H 0.4858 0.3488 0.5889 0.031 Uiso 1 1 calc R . . C5 C 0.2954(2) 0.39312(17) 0.57500(13) 0.0288(4) Uani 1 1 d . . . H5 H 0.3047 0.3939 0.6371 0.035 Uiso 1 1 calc R . . C6 C 0.1749(2) 0.41833(17) 0.51236(13) 0.0268(4) Uani 1 1 d . . . H6 H 0.0990 0.4359 0.5295 0.032 Uiso 1 1 calc R . . C7 C 0.17014(18) 0.41677(15) 0.42318(12) 0.0221(4) Uani 1 1 d . . . C8 C 0.63324(18) 0.32641(16) 0.48705(12) 0.0250(4) Uani 1 1 d . . . H8A H 0.6543 0.3935 0.5240 0.037 Uiso 1 1 calc R . . H8B H 0.7005 0.3152 0.4571 0.037 Uiso 1 1 calc R . . H8C H 0.6323 0.2623 0.5251 0.037 Uiso 1 1 calc R . . C9 C 0.21455(18) 0.10180(15) 0.44426(12) 0.0221(4) Uani 1 1 d . . . C10 C 0.2638(2) 0.10219(18) 0.53693(13) 0.0301(4) Uani 1 1 d . . . H10 H 0.3539 0.0835 0.5667 0.036 Uiso 1 1 calc R . . C11 C 0.1802(2) 0.13021(18) 0.58579(14) 0.0325(5) Uani 1 1 d . . . H11 H 0.2136 0.1303 0.6494 0.039 Uiso 1 1 calc R . . C12 C 0.0484(2) 0.15815(17) 0.54326(14) 0.0303(4) Uani 1 1 d . . . C13 C 0.0018(2) 0.15781(18) 0.45027(14) 0.0336(5) Uani 1 1 d . . . H13 H -0.0881 0.1771 0.4204 0.040 Uiso 1 1 calc R . . C14 C 0.08363(19) 0.12997(17) 0.40012(13) 0.0291(4) Uani 1 1 d . . . H14 H 0.0506 0.1302 0.3365 0.035 Uiso 1 1 calc R . . C15 C -0.0409(2) 0.1910(2) 0.59709(17) 0.0449(6) Uani 1 1 d . . . H15A H -0.0522 0.2717 0.5950 0.067 Uiso 1 1 calc R . . H15B H -0.0010 0.1672 0.6594 0.067 Uiso 1 1 calc R . . H15C H -0.1276 0.1553 0.5718 0.067 Uiso 1 1 calc R . . C16 C 0.55601(17) 0.21573(15) 0.30481(11) 0.0211(4) Uani 1 1 d D . . H2N H 0.504(2) 0.1189(18) 0.4472(14) 0.022(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02190(12) 0.04609(15) 0.02841(12) -0.00159(9) 0.00530(8) 0.00739(9) N1 0.0212(8) 0.0191(8) 0.0224(8) -0.0016(6) 0.0072(6) 0.0001(6) N2 0.0183(8) 0.0214(8) 0.0211(8) 0.0029(6) 0.0039(6) -0.0011(7) O1 0.0270(7) 0.0355(8) 0.0215(7) -0.0039(6) 0.0047(5) -0.0070(6) O2 0.0297(7) 0.0184(7) 0.0311(7) -0.0004(5) 0.0101(6) -0.0008(6) S1 0.0202(2) 0.0204(2) 0.0202(2) -0.00154(17) 0.00656(17) -0.00255(18) S2 0.0305(8) 0.0250(8) 0.0296(7) 0.0006(6) 0.0152(6) 0.0046(6) C17 0.023(2) 0.040(3) 0.024(3) 0.001(2) 0.0116(18) 0.002(2) C18 0.031(3) 0.038(3) 0.021(2) -0.002(2) 0.010(2) -0.006(2) C19 0.043(4) 0.030(4) 0.032(3) 0.002(3) 0.014(2) 0.000(3) S2A 0.0389(9) 0.0279(10) 0.0340(8) 0.0022(7) 0.0256(6) -0.0058(7) C17A 0.022(2) 0.043(3) 0.023(2) -0.008(2) 0.0176(19) -0.002(2) C18A 0.031(3) 0.036(3) 0.025(3) -0.002(2) 0.008(2) 0.006(2) C19A 0.041(4) 0.042(5) 0.029(3) 0.006(3) 0.014(2) -0.011(3) C1 0.0202(9) 0.0190(9) 0.0196(8) 0.0009(7) 0.0065(7) 0.0004(7) C2 0.0214(9) 0.0194(9) 0.0210(9) -0.0002(7) 0.0072(7) 0.0003(7) C3 0.0224(9) 0.0149(8) 0.0231(9) -0.0006(7) 0.0072(7) -0.0004(7) C4 0.0268(10) 0.0261(10) 0.0228(9) -0.0003(7) 0.0065(8) 0.0031(8) C5 0.0351(11) 0.0315(11) 0.0224(9) 0.0007(8) 0.0128(8) 0.0042(9) C6 0.0272(10) 0.0289(10) 0.0292(10) -0.0005(8) 0.0158(8) 0.0030(8) C7 0.0201(9) 0.0197(9) 0.0255(9) -0.0013(7) 0.0056(7) 0.0004(8) C8 0.0215(9) 0.0254(10) 0.0267(9) -0.0033(8) 0.0058(7) -0.0013(8) C9 0.0213(9) 0.0219(9) 0.0253(9) 0.0017(7) 0.0106(7) -0.0020(8) C10 0.0255(10) 0.0374(12) 0.0271(10) 0.0061(8) 0.0078(8) 0.0062(9) C11 0.0359(11) 0.0389(12) 0.0269(10) 0.0078(9) 0.0156(9) 0.0068(10) C12 0.0318(11) 0.0251(10) 0.0408(12) 0.0069(9) 0.0213(9) 0.0020(9) C13 0.0208(10) 0.0374(12) 0.0427(12) 0.0021(9) 0.0099(9) 0.0020(9) C14 0.0247(10) 0.0333(11) 0.0265(10) 0.0001(8) 0.0043(8) -0.0011(9) C15 0.0414(13) 0.0503(15) 0.0535(14) 0.0083(12) 0.0297(11) 0.0086(12) C16 0.0211(9) 0.0219(9) 0.0204(9) -0.0006(7) 0.0066(7) 0.0012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C7 1.9090(18) . ? N1 C7 1.316(2) . ? N1 C3 1.359(2) . ? N2 C1 1.462(2) . ? N2 S1 1.6100(16) . ? N2 H2N 0.76(2) . ? O1 S1 1.4335(14) . ? O2 S1 1.4411(13) . ? S1 C9 1.7693(18) . ? S2 C16 1.696(3) . ? S2 C17 1.708(7) . ? C17 C18 1.351(11) . ? C17 H17A 0.9500 . ? C18 C19 1.406(11) . ? C18 H18A 0.9500 . ? C19 C16 1.405(10) . ? C19 H19A 0.9500 . ? S2A C16 1.676(3) . ? S2A C17A 1.735(7) . ? C17A C18A 1.368(11) . ? C17A H17B 0.9500 . ? C18A C19A 1.414(12) . ? C18A H18B 0.9500 . ? C19A C16 1.374(9) . ? C19A H19B 0.9500 . ? C1 C16 1.514(2) . ? C1 C2 1.550(2) . ? C1 H1 1.0000 . ? C2 C3 1.509(2) . ? C2 C8 1.529(2) . ? C2 H2 1.0000 . ? C3 C4 1.389(2) . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C6 C7 1.388(3) . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.385(3) . ? C9 C14 1.387(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 C13 1.389(3) . ? C12 C15 1.509(3) . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C7 N1 C3 117.11(15) . . ? C1 N2 S1 125.11(13) . . ? C1 N2 H2N 121.5(16) . . ? S1 N2 H2N 113.4(16) . . ? O1 S1 O2 119.65(8) . . ? O1 S1 N2 108.18(8) . . ? O2 S1 N2 105.43(8) . . ? O1 S1 C9 108.24(9) . . ? O2 S1 C9 106.09(8) . . ? N2 S1 C9 108.89(8) . . ? C16 S2 C17 93.3(3) . . ? C18 C17 S2 111.4(5) . . ? C18 C17 H17A 124.3 . . ? S2 C17 H17A 124.3 . . ? C17 C18 C19 112.9(6) . . ? C17 C18 H18A 123.6 . . ? C19 C18 H18A 123.5 . . ? C16 C19 C18 112.7(7) . . ? C16 C19 H19A 123.6 . . ? C18 C19 H19A 123.6 . . ? C16 S2A C17A 92.2(3) . . ? C18A C17A S2A 110.8(5) . . ? C18A C17A H17B 124.6 . . ? S2A C17A H17B 124.6 . . ? C17A C18A C19A 112.2(7) . . ? C17A C18A H18B 123.9 . . ? C19A C18A H18B 123.9 . . ? C16 C19A C18A 112.6(7) . . ? C16 C19A H19B 123.7 . . ? C18A C19A H19B 123.7 . . ? N2 C1 C16 110.05(14) . . ? N2 C1 C2 111.35(14) . . ? C16 C1 C2 111.35(14) . . ? N2 C1 H1 108.0 . . ? C16 C1 H1 108.0 . . ? C2 C1 H1 108.0 . . ? C3 C2 C8 113.85(15) . . ? C3 C2 C1 109.72(14) . . ? C8 C2 C1 112.01(15) . . ? C3 C2 H2 107.0 . . ? C8 C2 H2 107.0 . . ? C1 C2 H2 107.0 . . ? N1 C3 C4 121.45(17) . . ? N1 C3 C2 114.31(15) . . ? C4 C3 C2 124.23(16) . . ? C5 C4 C3 119.59(17) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 119.37(17) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 116.69(18) . . ? C5 C6 H6 121.7 . . ? C7 C6 H6 121.7 . . ? N1 C7 C6 125.78(17) . . ? N1 C7 Br1 116.03(13) . . ? C6 C7 Br1 118.18(14) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 120.89(17) . . ? C10 C9 S1 118.22(14) . . ? C14 C9 S1 120.78(14) . . ? C9 C10 C11 119.24(18) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C12 121.06(19) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 118.52(19) . . ? C13 C12 C15 120.85(19) . . ? C11 C12 C15 120.6(2) . . ? C14 C13 C12 121.37(19) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C9 118.92(18) . . ? C13 C14 H14 120.5 . . ? C9 C14 H14 120.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C19A C16 C19 105.1(7) . . ? C19A C16 C1 126.6(5) . . ? C19 C16 C1 128.0(4) . . ? C19A C16 S2A 112.2(5) . . ? C1 C16 S2A 121.18(16) . . ? C19 C16 S2 109.6(4) . . ? C1 C16 S2 122.34(16) . . ? S2A C16 S2 116.44(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N2 S1 O1 25.20(17) . . . . ? C1 N2 S1 O2 154.31(14) . . . . ? C1 N2 S1 C9 -92.22(16) . . . . ? C16 S2 C17 C18 -0.02(15) . . . . ? S2 C17 C18 C19 0.0(2) . . . . ? C17 C18 C19 C16 0.1(4) . . . . ? C16 S2A C17A C18A 0.14(15) . . . . ? S2A C17A C18A C19A 0.07(19) . . . . ? C17A C18A C19A C16 -0.3(4) . . . . ? S1 N2 C1 C16 -109.45(16) . . . . ? S1 N2 C1 C2 126.58(14) . . . . ? N2 C1 C2 C3 -64.89(18) . . . . ? C16 C1 C2 C3 171.87(14) . . . . ? N2 C1 C2 C8 62.57(19) . . . . ? C16 C1 C2 C8 -60.66(19) . . . . ? C7 N1 C3 C4 -0.4(3) . . . . ? C7 N1 C3 C2 -179.89(16) . . . . ? C8 C2 C3 N1 171.87(15) . . . . ? C1 C2 C3 N1 -61.70(19) . . . . ? C8 C2 C3 C4 -7.6(3) . . . . ? C1 C2 C3 C4 118.82(19) . . . . ? N1 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 C5 179.79(18) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C7 -0.9(3) . . . . ? C3 N1 C7 C6 -0.2(3) . . . . ? C3 N1 C7 Br1 178.71(12) . . . . ? C5 C6 C7 N1 0.9(3) . . . . ? C5 C6 C7 Br1 -178.04(15) . . . . ? O1 S1 C9 C10 -178.62(15) . . . . ? O2 S1 C9 C10 51.81(17) . . . . ? N2 S1 C9 C10 -61.24(18) . . . . ? O1 S1 C9 C14 5.07(19) . . . . ? O2 S1 C9 C14 -124.51(16) . . . . ? N2 S1 C9 C14 122.45(17) . . . . ? C14 C9 C10 C11 0.6(3) . . . . ? S1 C9 C10 C11 -175.70(17) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C10 C11 C12 C15 -178.6(2) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C15 C12 C13 C14 178.7(2) . . . . ? C12 C13 C14 C9 0.1(3) . . . . ? C10 C9 C14 C13 -0.6(3) . . . . ? S1 C9 C14 C13 175.66(16) . . . . ? C18A C19A C16 C19 -3.9(6) . . . . ? C18A C19A C16 C1 -177.6(4) . . . . ? C18A C19A C16 S2A 0.4(4) . . . . ? C18A C19A C16 S2 140(5) . . . . ? C18 C19 C16 C19A 3.4(6) . . . . ? C18 C19 C16 C1 177.0(4) . . . . ? C18 C19 C16 S2A -147(3) . . . . ? C18 C19 C16 S2 -0.1(4) . . . . ? N2 C1 C16 C19A 11.4(4) . . . . ? C2 C1 C16 C19A 135.4(4) . . . . ? N2 C1 C16 C19 -160.9(4) . . . . ? C2 C1 C16 C19 -36.9(4) . . . . ? N2 C1 C16 S2A -166.49(16) . . . . ? C2 C1 C16 S2A -42.5(2) . . . . ? N2 C1 C16 S2 15.9(2) . . . . ? C2 C1 C16 S2 139.88(17) . . . . ? C17A S2A C16 C19A -0.3(3) . . . . ? C17A S2A C16 C19 31(3) . . . . ? C17A S2A C16 C1 177.8(3) . . . . ? C17A S2A C16 S2 -4.4(3) . . . . ? C17 S2 C16 C19A -37(5) . . . . ? C17 S2 C16 C19 0.1(3) . . . . ? C17 S2 C16 C1 -177.2(3) . . . . ? C17 S2 C16 S2A 5.1(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 N2 H2N O2 0.76(2) 2.24(2) 2.983(2) 166(2) 3_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.379 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.058