# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Maria Duarte' _publ_contact_author_email teresa.duarte@ist.utl.pt _publ_section_title ; Evaluation of intermolecular interactions in thioxanthones derivatives: substituent effect on crystal diversity ; loop_ _publ_author_name C.Jacob M.P.Robalo 'M.M.da Piedade' M.Duarte # Attachment '- compound 1_4and6.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 798531' #TrackingRef '- compound 1_4and6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 Br N O4 S' _chemical_formula_weight 354.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' S S 0.3331 0.5567 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.049(2) _cell_length_b 11.888(3) _cell_length_c 16.218(5) _cell_angle_alpha 86.150(10) _cell_angle_beta 84.5560(14) _cell_angle_gamma 86.2980(11) _cell_volume 1347.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 17.23 _cell_measurement_theta_max 21.05 _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 5.739 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.4421 _exptl_absorpt_correction_T_max 0.6567 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4754 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 66.95 _reflns_number_total 4754 _reflns_number_gt 2769 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0985P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4754 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1695 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _refine_ls_shift/su_max 0.109 _refine_ls_shift/su_mean 0.003 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 0.87326(13) -0.13279(6) 0.07474(5) 0.0775(3) Uani 1 1 d . . . C1A C 0.6741(11) -0.0298(5) 0.1139(3) 0.0538(17) Uani 1 1 d . . . C2A C 0.7193(10) 0.0736(5) 0.1371(3) 0.0512(16) Uani 1 1 d . . . H2A H 0.840(8) 0.0921(14) 0.1326(4) 0.061 Uiso 1 1 calc R . . C3A C 0.5767(9) 0.1484(5) 0.1673(3) 0.0528(17) Uani 1 1 d . . . H3A H 0.603(2) 0.210(5) 0.1819(13) 0.063 Uiso 1 1 calc R . . C4A C 0.3881(9) 0.1197(4) 0.1734(3) 0.0452(15) Uani 1 1 d . . . C5A C 0.3432(11) 0.0173(5) 0.1497(4) 0.0581(17) Uani 1 1 d . . . H5A H 0.199(9) -0.0030(14) 0.1526(4) 0.070 Uiso 1 1 calc R . . C6A C 0.4879(11) -0.0607(5) 0.1215(4) 0.0612(19) Uani 1 1 d . . . H6A H 0.461(3) -0.126(6) 0.1093(11) 0.073 Uiso 1 1 calc R . . S1A S 0.2063(2) 0.21379(12) 0.21900(8) 0.0513(4) Uani 1 1 d . . . C7A C 0.2106(8) 0.3315(4) 0.1467(3) 0.0394(13) Uani 1 1 d . . . C8A C 0.2934(8) 0.3193(5) 0.0656(3) 0.0422(13) Uani 1 1 d . . . H8A H 0.351(3) 0.244(4) 0.0495(10) 0.051 Uiso 1 1 calc R . . C9A C 0.2966(8) 0.4095(5) 0.0081(3) 0.0451(14) Uani 1 1 d . . . H9A H 0.350(3) 0.4002(7) -0.046(3) 0.054 Uiso 1 1 calc R . . C10A C 0.2204(8) 0.5147(4) 0.0309(3) 0.0388(13) Uani 1 1 d . . . N2A N 0.2274(7) 0.6110(4) -0.0297(3) 0.0539(14) Uani 1 1 d . . . O1A O 0.2763(7) 0.5917(4) -0.1026(2) 0.0652(13) Uani 1 1 d . . . O2A O 0.1856(8) 0.7030(4) -0.0062(3) 0.0892(19) Uani 1 1 d . . . C11A C 0.1363(8) 0.5303(5) 0.1094(3) 0.0424(14) Uani 1 1 d . . . H11A H 0.088(4) 0.596(5) 0.1223(10) 0.051 Uiso 1 1 calc R . . C12A C 0.1298(8) 0.4389(4) 0.1679(3) 0.0353(12) Uani 1 1 d . . . C13A C 0.0273(8) 0.4579(4) 0.2507(3) 0.0392(13) Uani 1 1 d . . . O3A O -0.0049(6) 0.3799(3) 0.3028(2) 0.0536(11) Uani 1 1 d . . . O4A O -0.0225(6) 0.5633(3) 0.2628(2) 0.0550(11) Uani 1 1 d . . . H4A H -0.0682 0.5688 0.3109 0.083 Uiso 1 1 calc R . . Br2 Br 0.96129(17) -0.12332(8) 0.32045(5) 0.1174(5) Uani 1 1 d . . . C1B C 0.7890(13) -0.0130(6) 0.3693(4) 0.065(2) Uani 1 1 d . . . C2B C 0.8556(12) 0.0617(7) 0.4161(5) 0.078(3) Uani 1 1 d . . . H2B H 0.976(11) 0.0592(7) 0.4231(8) 0.093 Uiso 1 1 calc R . . C3B C 0.7312(11) 0.1437(5) 0.4537(4) 0.0609(19) Uani 1 1 d . . . H3B H 0.773(4) 0.191(4) 0.484(3) 0.073 Uiso 1 1 calc R . . C4B C 0.5421(9) 0.1468(4) 0.4416(3) 0.0447(15) Uani 1 1 d . . . C5B C 0.4750(10) 0.0696(5) 0.3939(3) 0.0522(16) Uani 1 1 d . . . H5B H 0.344(9) 0.0727(5) 0.3853(7) 0.063 Uiso 1 1 calc R . . C6B C 0.5992(12) -0.0137(5) 0.3579(3) 0.061(2) Uani 1 1 d . . . H6B H 0.553(4) -0.070(4) 0.326(2) 0.073 Uiso 1 1 calc R . . S1B S 0.3837(2) 0.24727(12) 0.49418(8) 0.0550(5) Uani 1 1 d . . . C7B C 0.3979(8) 0.3679(4) 0.4252(3) 0.0364(12) Uani 1 1 d . . . C8B C 0.4954(8) 0.3624(4) 0.3461(3) 0.0421(14) Uani 1 1 d . . . H8B H 0.555(4) 0.294(4) 0.3303(10) 0.050 Uiso 1 1 calc R . . C9B C 0.5047(8) 0.4564(4) 0.2908(3) 0.0411(14) Uani 1 1 d . . . H9B H 0.567(4) 0.4514(5) 0.238(3) 0.049 Uiso 1 1 calc R . . C10B C 0.4187(8) 0.5573(4) 0.3157(3) 0.0369(12) Uani 1 1 d . . . N2B N 0.4292(8) 0.6578(4) 0.2575(3) 0.0517(13) Uani 1 1 d . . . O1B O 0.5042(8) 0.6452(4) 0.1879(2) 0.0857(18) Uani 1 1 d . . . O2B O 0.3657(8) 0.7471(4) 0.2823(3) 0.0864(18) Uani 1 1 d . . . C11B C 0.3238(7) 0.5672(4) 0.3928(3) 0.0374(12) Uani 1 1 d . . . H11B H 0.268(4) 0.637(4) 0.4081(10) 0.045 Uiso 1 1 calc R . . C12B C 0.3111(7) 0.4723(4) 0.4483(3) 0.0337(12) Uani 1 1 d . . . C13B C 0.2133(8) 0.4894(4) 0.5321(3) 0.0361(12) Uani 1 1 d . . . O3B O 0.1972(6) 0.4124(3) 0.58613(19) 0.0486(10) Uani 1 1 d . . . O4B O 0.1408(6) 0.5922(3) 0.5424(2) 0.0488(10) Uani 1 1 d . . . H4B H 0.0751 0.5936 0.5869 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0984(6) 0.0566(4) 0.0736(5) -0.0247(4) 0.0130(4) 0.0167(4) C1A 0.087(5) 0.036(3) 0.034(3) -0.003(2) 0.013(3) 0.004(3) C2A 0.066(4) 0.041(3) 0.044(3) -0.005(3) 0.011(3) -0.001(3) C3A 0.077(5) 0.036(3) 0.045(3) -0.012(3) 0.011(3) -0.010(3) C4A 0.072(4) 0.032(3) 0.025(3) 0.004(2) 0.015(3) 0.004(3) C5A 0.073(5) 0.045(3) 0.054(4) -0.003(3) 0.011(3) -0.011(3) C6A 0.094(6) 0.029(3) 0.059(4) -0.012(3) 0.014(4) -0.010(3) S1A 0.0752(11) 0.0402(7) 0.0315(7) 0.0027(6) 0.0216(7) 0.0054(7) C7A 0.057(4) 0.036(3) 0.023(2) -0.003(2) 0.010(2) -0.006(3) C8A 0.060(4) 0.041(3) 0.022(2) -0.003(2) 0.006(2) 0.005(3) C9A 0.062(4) 0.052(3) 0.018(2) -0.004(2) 0.013(2) 0.003(3) C10A 0.050(3) 0.042(3) 0.020(2) 0.008(2) 0.010(2) 0.001(3) N2A 0.069(3) 0.052(3) 0.034(3) 0.009(2) 0.018(2) 0.005(3) O1A 0.099(3) 0.069(3) 0.023(2) 0.0057(19) 0.017(2) -0.012(3) O2A 0.138(5) 0.054(3) 0.058(3) 0.013(2) 0.049(3) 0.026(3) C11A 0.056(4) 0.041(3) 0.026(3) -0.002(2) 0.013(2) 0.002(3) C12A 0.049(3) 0.035(2) 0.021(2) -0.005(2) 0.008(2) -0.005(2) C13A 0.052(3) 0.035(2) 0.026(3) -0.004(2) 0.014(2) 0.002(2) O3A 0.082(3) 0.046(2) 0.0252(18) 0.0013(17) 0.0282(18) 0.002(2) O4A 0.085(3) 0.047(2) 0.0258(19) -0.0048(16) 0.023(2) 0.012(2) Br2 0.1625(10) 0.0793(6) 0.0839(6) 0.0140(5) 0.0687(6) 0.0595(6) C1B 0.093(6) 0.045(3) 0.046(4) 0.011(3) 0.030(4) 0.023(4) C2B 0.069(5) 0.061(4) 0.090(6) 0.027(4) 0.024(4) 0.016(4) C3B 0.087(6) 0.043(3) 0.052(4) -0.003(3) 0.003(3) -0.004(4) C4B 0.066(4) 0.032(3) 0.029(3) 0.011(2) 0.017(3) 0.005(3) C5B 0.076(4) 0.039(3) 0.037(3) 0.006(3) 0.008(3) 0.001(3) C6B 0.114(7) 0.032(3) 0.031(3) -0.001(2) 0.011(3) 0.003(4) S1B 0.0885(12) 0.0373(7) 0.0298(7) 0.0065(6) 0.0283(7) 0.0102(7) C7B 0.054(3) 0.031(2) 0.020(2) 0.0019(19) 0.015(2) -0.004(2) C8B 0.068(4) 0.030(2) 0.024(2) -0.001(2) 0.015(2) 0.002(3) C9B 0.063(4) 0.037(3) 0.018(2) -0.003(2) 0.019(2) 0.000(3) C10B 0.051(3) 0.036(3) 0.022(2) 0.003(2) 0.010(2) -0.006(2) N2B 0.077(4) 0.035(2) 0.036(3) 0.007(2) 0.021(2) 0.002(2) O1B 0.156(5) 0.055(3) 0.031(2) 0.012(2) 0.050(3) 0.009(3) O2B 0.140(5) 0.041(2) 0.062(3) 0.014(2) 0.045(3) 0.022(3) C11B 0.052(3) 0.030(2) 0.027(3) -0.003(2) 0.012(2) 0.001(2) C12B 0.048(3) 0.031(2) 0.019(2) 0.0027(19) 0.011(2) -0.001(2) C13B 0.049(3) 0.032(2) 0.025(2) -0.006(2) 0.009(2) -0.001(2) O3B 0.077(3) 0.0389(19) 0.0224(17) 0.0023(15) 0.0234(17) 0.0104(19) O4B 0.071(3) 0.044(2) 0.0256(18) -0.0046(16) 0.0250(17) 0.005(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1A 1.894(6) . ? C1A C6A 1.378(10) . ? C1A C2A 1.375(8) . ? C2A C3A 1.375(8) . ? C2A H2A 0.8898 . ? C3A C4A 1.387(9) . ? C3A H3A 0.8267 . ? C4A C5A 1.367(8) . ? C4A S1A 1.785(5) . ? C5A C6A 1.398(9) . ? C5A H5A 1.0573 . ? C6A H6A 0.8554 . ? S1A C7A 1.765(5) . ? C7A C8A 1.399(6) . ? C7A C12A 1.415(7) . ? C8A C9A 1.373(7) . ? C8A H8A 0.9933 . ? C9A C10A 1.388(7) . ? C9A H9A 0.9290 . ? C10A C11A 1.372(6) . ? C10A N2A 1.458(6) . ? N2A O2A 1.192(7) . ? N2A O1A 1.232(6) . ? C11A C12A 1.394(7) . ? C11A H11A 0.8569 . ? C12A C13A 1.487(6) . ? C13A O3A 1.229(6) . ? C13A O4A 1.301(6) . ? O4A H4A 0.8200 . ? Br2 C1B 1.890(6) . ? C1B C2B 1.340(11) . ? C1B C6B 1.369(10) . ? C2B C3B 1.399(9) . ? C2B H2B 0.8676 . ? C3B C4B 1.364(9) . ? C3B H3B 0.8573 . ? C4B C5B 1.374(8) . ? C4B S1B 1.784(5) . ? C5B C6B 1.399(8) . ? C5B H5B 0.9465 . ? C6B H6B 0.9639 . ? S1B C7B 1.761(5) . ? C7B C8B 1.401(6) . ? C7B C12B 1.405(6) . ? C8B C9B 1.385(6) . ? C8B H8B 0.9296 . ? C9B C10B 1.376(7) . ? C9B H9B 0.9233 . ? C10B C11B 1.369(6) . ? C10B N2B 1.473(6) . ? N2B O2B 1.204(6) . ? N2B O1B 1.215(5) . ? C11B C12B 1.398(6) . ? C11B H11B 0.9335 . ? C12B C13B 1.484(6) . ? C13B O3B 1.228(6) . ? C13B O4B 1.309(6) . ? O4B H4B 0.8200 . ? 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 C6A C1A C2A 121.1(6) . . ? C6A C1A Br1 119.9(4) . . ? C2A C1A Br1 119.0(5) . . ? C1A C2A C3A 119.7(6) . . ? C1A C2A H2A 120.1 . . ? C3A C2A H2A 120.1 . . ? C4A C3A C2A 119.9(6) . . ? C4A C3A H3A 120.1 . . ? C2A C3A H3A 120.1 . . ? C5A C4A C3A 120.3(6) . . ? C5A C4A S1A 120.2(5) . . ? C3A C4A S1A 119.3(4) . . ? C4A C5A C6A 120.1(7) . . ? C4A C5A H5A 120.0 . . ? C6A C5A H5A 120.0 . . ? C1A C6A C5A 118.8(6) . . ? C1A C6A H6A 120.6 . . ? C5A C6A H6A 120.6 . . ? C7A S1A C4A 102.3(2) . . ? C8A C7A C12A 118.5(4) . . ? C8A C7A S1A 119.8(4) . . ? C12A C7A S1A 121.7(3) . . ? C9A C8A C7A 120.8(5) . . ? C9A C8A H8A 119.6 . . ? C7A C8A H8A 119.6 . . ? C8A C9A C10A 119.7(4) . . ? C8A C9A H9A 120.1 . . ? C10A C9A H9A 120.1 . . ? C11A C10A C9A 121.4(5) . . ? C11A C10A N2A 118.8(5) . . ? C9A C10A N2A 119.7(4) . . ? O2A N2A O1A 124.0(5) . . ? O2A N2A C10A 118.5(4) . . ? O1A N2A C10A 117.4(5) . . ? C10A C11A C12A 119.3(5) . . ? C10A C11A H11A 120.4 . . ? C12A C11A H11A 120.4 . . ? C11A C12A C7A 120.3(4) . . ? C11A C12A C13A 117.5(4) . . ? C7A C12A C13A 122.2(4) . . ? O3A C13A O4A 123.7(4) . . ? O3A C13A C12A 122.1(4) . . ? O4A C13A C12A 114.2(4) . . ? C13A O4A H4A 109.5 . . ? C2B C1B C6B 121.9(6) . . ? C2B C1B Br2 119.0(7) . . ? C6B C1B Br2 119.1(6) . . ? C1B C2B C3B 120.3(8) . . ? C1B C2B H2B 119.9 . . ? C3B C2B H2B 119.9 . . ? C4B C3B C2B 119.1(7) . . ? C4B C3B H3B 120.4 . . ? C2B C3B H3B 120.4 . . ? C3B C4B C5B 120.2(6) . . ? C3B C4B S1B 118.5(5) . . ? C5B C4B S1B 121.2(5) . . ? C4B C5B C6B 120.5(7) . . ? C4B C5B H5B 119.8 . . ? C6B C5B H5B 119.8 . . ? C1B C6B C5B 118.0(7) . . ? C1B C6B H6B 121.0 . . ? C5B C6B H6B 121.0 . . ? C7B S1B C4B 102.3(2) . . ? C8B C7B C12B 118.3(4) . . ? C8B C7B S1B 121.0(4) . . ? C12B C7B S1B 120.7(3) . . ? C9B C8B C7B 121.5(5) . . ? C9B C8B H8B 119.3 . . ? C7B C8B H8B 119.3 . . ? C10B C9B C8B 118.6(4) . . ? C10B C9B H9B 120.7 . . ? C8B C9B H9B 120.7 . . ? C11B C10B C9B 122.1(4) . . ? C11B C10B N2B 119.0(4) . . ? C9B C10B N2B 118.9(4) . . ? O2B N2B O1B 124.3(5) . . ? O2B N2B C10B 118.1(4) . . ? O1B N2B C10B 117.6(4) . . ? C10B C11B C12B 119.6(5) . . ? C10B C11B H11B 120.2 . . ? C12B C11B H11B 120.2 . . ? C11B C12B C7B 119.9(4) . . ? C11B C12B C13B 117.0(4) . . ? C7B C12B C13B 123.0(4) . . ? O3B C13B O4B 123.0(4) . . ? O3B C13B C12B 122.5(4) . . ? O4B C13B C12B 114.5(4) . . ? C13B O4B H4B 109.5 . . ? 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 C6A C1A C2A C3A -0.9(9) . . . . ? Br1 C1A C2A C3A -178.7(4) . . . . ? C1A C2A C3A C4A -0.7(9) . . . . ? C2A C3A C4A C5A 0.1(9) . . . . ? C2A C3A C4A S1A 175.9(4) . . . . ? C3A C4A C5A C6A 2.0(9) . . . . ? S1A C4A C5A C6A -173.7(5) . . . . ? C2A C1A C6A C5A 3.1(9) . . . . ? Br1 C1A C6A C5A -179.2(5) . . . . ? C4A C5A C6A C1A -3.6(9) . . . . ? C5A C4A S1A C7A -117.5(5) . . . . ? C3A C4A S1A C7A 66.7(5) . . . . ? C4A S1A C7A C8A 19.3(5) . . . . ? C4A S1A C7A C12A -161.5(5) . . . . ? C12A C7A C8A C9A 0.1(9) . . . . ? S1A C7A C8A C9A 179.3(5) . . . . ? C7A C8A C9A C10A 1.3(9) . . . . ? C8A C9A C10A C11A -1.9(9) . . . . ? C8A C9A C10A N2A 178.7(5) . . . . ? C11A C10A N2A O2A 10.8(9) . . . . ? C9A C10A N2A O2A -169.8(6) . . . . ? C11A C10A N2A O1A -169.1(5) . . . . ? C9A C10A N2A O1A 10.3(9) . . . . ? C9A C10A C11A C12A 1.0(9) . . . . ? N2A C10A C11A C12A -179.7(5) . . . . ? C10A C11A C12A C7A 0.5(9) . . . . ? C10A C11A C12A C13A -176.4(5) . . . . ? C8A C7A C12A C11A -1.1(8) . . . . ? S1A C7A C12A C11A 179.7(4) . . . . ? C8A C7A C12A C13A 175.7(5) . . . . ? S1A C7A C12A C13A -3.4(8) . . . . ? C11A C12A C13A O3A 171.5(6) . . . . ? C7A C12A C13A O3A -5.4(9) . . . . ? C11A C12A C13A O4A -9.2(8) . . . . ? C7A C12A C13A O4A 173.9(6) . . . . ? C6B C1B C2B C3B -1.3(10) . . . . ? Br2 C1B C2B C3B -179.4(5) . . . . ? C1B C2B C3B C4B -0.4(10) . . . . ? C2B C3B C4B C5B 0.7(8) . . . . ? C2B C3B C4B S1B 176.9(5) . . . . ? C3B C4B C5B C6B 0.7(8) . . . . ? S1B C4B C5B C6B -175.4(4) . . . . ? C2B C1B C6B C5B 2.6(9) . . . . ? Br2 C1B C6B C5B -179.3(4) . . . . ? C4B C5B C6B C1B -2.3(8) . . . . ? C3B C4B S1B C7B 86.9(5) . . . . ? C5B C4B S1B C7B -96.9(4) . . . . ? C4B S1B C7B C8B 8.2(6) . . . . ? C4B S1B C7B C12B -172.0(5) . . . . ? C12B C7B C8B C9B -1.0(9) . . . . ? S1B C7B C8B C9B 178.9(5) . . . . ? C7B C8B C9B C10B 1.2(9) . . . . ? C8B C9B C10B C11B -0.4(9) . . . . ? C8B C9B C10B N2B 179.5(5) . . . . ? C11B C10B N2B O2B 5.4(9) . . . . ? C9B C10B N2B O2B -174.6(6) . . . . ? C11B C10B N2B O1B -175.7(6) . . . . ? C9B C10B N2B O1B 4.4(9) . . . . ? C9B C10B C11B C12B -0.6(9) . . . . ? N2B C10B C11B C12B 179.4(5) . . . . ? C10B C11B C12B C7B 0.9(8) . . . . ? C10B C11B C12B C13B 177.6(5) . . . . ? C8B C7B C12B C11B -0.1(8) . . . . ? S1B C7B C12B C11B -180.0(4) . . . . ? C8B C7B C12B C13B -176.6(5) . . . . ? S1B C7B C12B C13B 3.6(8) . . . . ? C11B C12B C13B O3B -178.7(5) . . . . ? C7B C12B C13B O3B -2.1(9) . . . . ? C11B C12B C13B O4B 3.4(7) . . . . ? C7B C12B C13B O4B 180.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 66.95 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.667 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.096 #END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 798532' #TrackingRef '- compound 1_4and6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N2 O4 S' _chemical_formula_weight 290.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 16.309(4) _cell_length_b 6.7318(16) _cell_length_c 13.206(6) _cell_angle_alpha 90.00 _cell_angle_beta 121.757(9) _cell_angle_gamma 90.00 _cell_volume 1232.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8278 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 30.53 _reflns_number_total 2016 _reflns_number_gt 1228 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.0574P] 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 2016 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 N1 N 0.16645(17) 0.5000 -0.1437(2) 0.0269(6) Uani 1 2 d S . . H1A H 0.17057(19) 0.606(2) -0.1720(7) 0.032 Uiso 0.50 1 calc PR . . H1B H 0.1715(2) 0.394(2) -0.1712(7) 0.032 Uiso 0.50 1 calc PR . . C1 C 0.15114(19) 0.5000 -0.0503(2) 0.0194(6) Uani 1 2 d S . . C2 C 0.14256(13) 0.3220(3) -0.00306(16) 0.0214(5) Uani 1 1 d . . . H2 H 0.14829(18) 0.199(3) -0.0345(7) 0.026 Uiso 1 1 calc R . . C3 C 0.12572(13) 0.3221(3) 0.08936(16) 0.0196(4) Uani 1 1 d . . . H3 H 0.11950(19) 0.196(3) 0.1215(7) 0.023 Uiso 1 1 calc R . . C4 C 0.11763(18) 0.5000 0.1366(2) 0.0173(6) Uani 1 2 d S . . S1 S 0.08603(5) 0.5000 0.24626(6) 0.01785(18) Uani 1 2 d S . . C7 C 0.19839(18) 0.5000 0.3810(2) 0.0154(6) Uani 1 2 d S . . C8 C 0.28477(19) 0.5000 0.3812(2) 0.0183(6) Uani 1 2 d S . . H8 H 0.2821(2) 0.5000 0.306(2) 0.022 Uiso 1 2 calc SR . . C9 C 0.37298(19) 0.5000 0.4865(2) 0.0199(6) Uani 1 2 d S . . H9 H 0.4275(17) 0.5000 0.4853(2) 0.024 Uiso 1 2 calc SR . . C10 C 0.37751(18) 0.5000 0.5940(2) 0.0170(6) Uani 1 2 d S . . N2 N 0.47189(16) 0.5000 0.7055(2) 0.0210(5) Uani 1 2 d S . . O1 O 0.54473(14) 0.5000 0.69860(18) 0.0395(6) Uani 1 2 d S . . O2 O 0.47471(13) 0.5000 0.79982(16) 0.0216(5) Uani 1 2 d S . . C11 C 0.29541(19) 0.5000 0.5982(2) 0.0174(6) Uani 1 2 d S . . H11 H 0.2995(2) 0.5000 0.667(2) 0.021 Uiso 1 2 calc SR . . C12 C 0.20528(18) 0.5000 0.4926(2) 0.0152(6) Uani 1 2 d S . . C13 C 0.11735(19) 0.5000 0.4996(2) 0.0163(6) Uani 1 2 d S . . O3 O 0.03629(13) 0.5000 0.41042(16) 0.0248(5) Uani 1 2 d S . . O4 O 0.13353(13) 0.5000 0.60812(15) 0.0216(5) Uani 1 2 d S . . H4 H 0.0855 0.5404 0.6067 0.032 Uiso 0.50 1 calc PR . . 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 N1 0.0261(14) 0.0409(18) 0.0195(13) 0.000 0.0160(11) 0.000 C1 0.0132(13) 0.0318(18) 0.0109(13) 0.000 0.0048(11) 0.000 C2 0.0188(10) 0.0279(12) 0.0179(10) -0.0056(9) 0.0101(9) 0.0004(9) C3 0.0190(10) 0.0226(12) 0.0185(10) 0.0002(8) 0.0107(9) -0.0014(8) C4 0.0124(13) 0.0286(17) 0.0116(13) 0.000 0.0068(11) 0.000 S1 0.0119(3) 0.0297(5) 0.0123(3) 0.000 0.0066(3) 0.000 C7 0.0125(13) 0.0192(16) 0.0150(13) 0.000 0.0075(11) 0.000 C8 0.0160(13) 0.0265(17) 0.0175(14) 0.000 0.0123(12) 0.000 C9 0.0108(13) 0.0327(19) 0.0178(14) 0.000 0.0085(12) 0.000 C10 0.0113(12) 0.0230(16) 0.0136(13) 0.000 0.0044(11) 0.000 N2 0.0141(12) 0.0302(15) 0.0185(12) 0.000 0.0084(10) 0.000 O1 0.0110(10) 0.0848(19) 0.0231(12) 0.000 0.0091(9) 0.000 O2 0.0177(10) 0.0321(12) 0.0133(10) 0.000 0.0070(8) 0.000 C11 0.0176(14) 0.0219(17) 0.0161(14) 0.000 0.0112(12) 0.000 C12 0.0130(13) 0.0192(15) 0.0164(13) 0.000 0.0098(11) 0.000 C13 0.0166(13) 0.0186(16) 0.0163(13) 0.000 0.0106(12) 0.000 O3 0.0130(10) 0.0476(14) 0.0150(10) 0.000 0.0081(9) 0.000 O4 0.0137(10) 0.0404(14) 0.0130(9) 0.000 0.0088(8) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.381(3) . ? N1 H1A 0.8248 . ? N1 H1B 0.8248 . ? C1 C2 1.392(2) 6_565 ? C1 C2 1.392(2) . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 C4 1.388(2) . ? C3 H3 0.9771 . ? C4 C3 1.388(2) 6_565 ? C4 S1 1.775(2) . ? S1 C7 1.758(3) . ? C7 C8 1.408(3) . ? C7 C12 1.417(3) . ? C8 C9 1.377(4) . ? C8 H8 0.9774 . ? C9 C10 1.383(3) . ? C9 H9 0.8978 . ? C10 C11 1.369(3) . ? C10 N2 1.467(3) . ? N2 O2 1.222(3) . ? N2 O1 1.238(3) . ? C11 C12 1.396(4) . ? C11 H11 0.8820 . ? C12 C13 1.485(3) . ? C13 O3 1.223(3) . ? C13 O4 1.313(3) . ? O4 H4 0.8200 . ? 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 C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? N1 C1 C2 120.56(12) . 6_565 ? N1 C1 C2 120.56(12) . . ? C2 C1 C2 118.9(2) 6_565 . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.4(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C3 119.2(2) . 6_565 ? C3 C4 S1 120.24(12) . . ? C3 C4 S1 120.24(12) 6_565 . ? C7 S1 C4 103.31(12) . . ? C8 C7 C12 117.8(2) . . ? C8 C7 S1 120.7(2) . . ? C12 C7 S1 121.48(18) . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 121.1(2) . . ? C11 C10 N2 119.4(2) . . ? C9 C10 N2 119.5(2) . . ? O2 N2 O1 123.5(2) . . ? O2 N2 C10 118.7(2) . . ? O1 N2 C10 117.8(2) . . ? C10 C11 C12 119.8(2) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C7 120.3(2) . . ? C11 C12 C13 118.8(2) . . ? C7 C12 C13 120.9(2) . . ? O3 C13 O4 123.1(2) . . ? O3 C13 C12 122.0(2) . . ? O4 C13 C12 115.0(2) . . ? C13 O4 H4 109.5 . . ? 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 N1 C1 C2 C3 -179.0(2) . . . . ? C2 C1 C2 C3 0.0(4) 6_565 . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C3 0.6(4) . . . 6_565 ? C2 C3 C4 S1 174.68(16) . . . . ? C3 C4 S1 C7 93.0(2) . . . . ? C3 C4 S1 C7 -93.0(2) 6_565 . . . ? C4 S1 C7 C8 0.0 . . . . ? C4 S1 C7 C12 180.0 . . . . ? C12 C7 C8 C9 0.0 . . . . ? S1 C7 C8 C9 180.0 . . . . ? C7 C8 C9 C10 0.0 . . . . ? C8 C9 C10 C11 0.0 . . . . ? C8 C9 C10 N2 180.0 . . . . ? C11 C10 N2 O2 0.0 . . . . ? C9 C10 N2 O2 180.0 . . . . ? C11 C10 N2 O1 180.0 . . . . ? C9 C10 N2 O1 0.0 . . . . ? C9 C10 C11 C12 0.0 . . . . ? N2 C10 C11 C12 180.0 . . . . ? C10 C11 C12 C7 0.0 . . . . ? C10 C11 C12 C13 180.0 . . . . ? C8 C7 C12 C11 0.0 . . . . ? S1 C7 C12 C11 180.0 . . . . ? C8 C7 C12 C13 180.0 . . . . ? S1 C7 C12 C13 0.0 . . . . ? C11 C12 C13 O3 180.0 . . . . ? C7 C12 C13 O3 0.0 . . . . ? C11 C12 C13 O4 0.0 . . . . ? C7 C12 C13 O4 180.0 . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.388 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.080 #END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 798533' #TrackingRef '- compound 1_4and6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H6 Br N O3 S' _chemical_formula_weight 336.16 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' S S 0.3331 0.5567 '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 Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.772(3) _cell_length_b 11.979(4) _cell_length_c 13.235(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.844(5) _cell_angle_gamma 90.00 _cell_volume 1191.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.18 _cell_measurement_theta_max 22.35 _exptl_crystal_description plate _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.875 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 6.390 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.0066 _exptl_absorpt_correction_T_max 0.1470 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2088 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.92 _diffrn_reflns_theta_max 66.92 _reflns_number_total 2088 _reflns_number_gt 1503 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1747P)^2^+0.4435P] 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 2088 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1099 _refine_ls_R_factor_gt 0.0847 _refine_ls_wR_factor_ref 0.2477 _refine_ls_wR_factor_gt 0.2288 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.39337(15) -0.35020(8) 0.97730(10) 0.0619(5) Uani 1 1 d . . . C1 C 0.5826(10) -0.2828(5) 0.9308(5) 0.0298(14) Uani 1 1 d . . . C2 C 0.7144(9) -0.3512(5) 0.9064(5) 0.0282(14) Uani 1 1 d . . . H2 H 0.7066 -0.4285 0.9102 0.034 Uiso 1 1 calc R . . C3 C 0.8539(10) -0.3027(6) 0.8772(5) 0.0331(16) Uani 1 1 d . . . H3 H 0.9419 -0.3471 0.8616 0.040 Uiso 1 1 calc R . . C4 C 0.8638(9) -0.1856(5) 0.8706(5) 0.0246(13) Uani 1 1 d . . . C5 C 0.7303(8) -0.1178(5) 0.8931(5) 0.0233(13) Uani 1 1 d . . . C6 C 0.5909(9) -0.1682(6) 0.9239(5) 0.0301(14) Uani 1 1 d . . . H6 H 0.5027 -0.1243 0.9400 0.036 Uiso 1 1 calc R . . S1 S 1.0470(2) -0.13466(14) 0.83124(16) 0.0360(5) Uani 1 1 d . . . C7 C 1.0275(8) 0.0082(5) 0.8392(5) 0.0255(13) Uani 1 1 d . . . C8 C 1.1697(9) 0.0712(7) 0.8201(6) 0.0364(16) Uani 1 1 d . . . H8 H 1.2651 0.0349 0.8042 0.044 Uiso 1 1 calc R . . C9 C 1.1681(9) 0.1852(6) 0.8248(5) 0.0332(15) Uani 1 1 d . . . H9 H 1.2610 0.2267 0.8114 0.040 Uiso 1 1 calc R . . C10 C 1.0270(9) 0.2377(6) 0.8495(5) 0.0291(14) Uani 1 1 d . . . N2 N 1.0202(9) 0.3615(5) 0.8527(5) 0.0357(15) Uani 1 1 d . . . O1 O 0.8960(9) 0.4069(4) 0.8728(6) 0.0561(17) Uani 1 1 d . . . O2 O 1.1432(9) 0.4115(5) 0.8316(6) 0.0598(17) Uani 1 1 d . . . C11 C 0.8854(8) 0.1799(5) 0.8686(5) 0.0228(13) Uani 1 1 d . . . H11 H 0.7916 0.2184 0.8842 0.027 Uiso 1 1 calc R . . C12 C 0.8830(8) 0.0629(5) 0.8644(5) 0.0255(13) Uani 1 1 d . . . C13 C 0.7290(8) 0.0047(5) 0.8852(5) 0.0270(14) Uani 1 1 d . . . O3 O 0.6028(7) 0.0597(4) 0.8966(6) 0.0506(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0628(7) 0.0547(6) 0.0708(9) 0.0107(5) 0.0219(6) -0.0020(4) C1 0.038(4) 0.031(3) 0.019(3) 0.001(3) 0.004(3) -0.003(3) C2 0.033(3) 0.029(3) 0.017(3) 0.000(3) -0.004(3) 0.006(2) C3 0.040(4) 0.037(3) 0.016(3) -0.003(3) -0.005(3) 0.014(3) C4 0.030(3) 0.029(3) 0.012(3) -0.003(2) 0.001(3) -0.001(2) C5 0.018(3) 0.032(3) 0.016(3) -0.004(2) -0.003(2) 0.006(2) C6 0.033(3) 0.036(3) 0.016(3) 0.002(3) -0.004(3) 0.008(3) S1 0.0311(9) 0.0426(9) 0.0363(11) -0.0038(8) 0.0122(8) 0.0070(6) C7 0.026(3) 0.037(3) 0.011(3) 0.001(2) 0.000(3) 0.005(2) C8 0.021(3) 0.061(4) 0.024(4) 0.006(3) 0.000(3) -0.001(3) C9 0.032(4) 0.050(4) 0.012(3) -0.002(3) -0.004(3) -0.010(3) C10 0.031(3) 0.043(4) 0.008(3) -0.005(3) -0.005(3) -0.005(3) N2 0.048(4) 0.044(3) 0.011(3) 0.002(2) -0.002(3) -0.012(3) O1 0.066(4) 0.035(3) 0.071(5) -0.004(3) 0.024(4) 0.002(3) O2 0.065(4) 0.057(3) 0.059(4) 0.003(3) 0.019(4) -0.018(3) C11 0.026(3) 0.029(3) 0.009(3) 0.000(2) -0.002(3) 0.003(2) C12 0.026(3) 0.038(3) 0.008(3) -0.006(3) -0.003(3) -0.002(2) C13 0.020(3) 0.038(3) 0.022(3) -0.008(3) 0.002(3) 0.000(2) O3 0.033(3) 0.039(2) 0.085(5) -0.003(3) 0.024(3) 0.004(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.912(7) . ? C1 C6 1.379(9) . ? C1 C2 1.412(10) . ? C2 C3 1.370(11) . ? C2 H2 0.9300 . ? C3 C4 1.408(9) . ? C3 H3 0.9300 . ? C4 C5 1.409(8) . ? C4 S1 1.746(7) . ? C5 C6 1.390(10) . ? C5 C13 1.471(9) . ? C6 H6 0.9300 . ? S1 C7 1.724(7) . ? C7 C12 1.412(8) . ? C7 C8 1.414(9) . ? C8 C9 1.367(11) . ? C8 H8 0.9300 . ? C9 C10 1.374(10) . ? C9 H9 0.9300 . ? C10 C11 1.377(9) . ? C10 N2 1.486(9) . ? N2 O1 1.196(9) . ? N2 O2 1.219(9) . ? C11 C12 1.402(9) . ? C11 H11 0.9300 . ? C12 C13 1.471(9) . ? C13 O3 1.222(8) . ? 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 C6 C1 C2 120.9(6) . . ? C6 C1 Br1 119.6(5) . . ? C2 C1 Br1 119.4(5) . . ? C3 C2 C1 119.4(5) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.0(6) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.4(6) . . ? C3 C4 S1 115.4(5) . . ? C5 C4 S1 124.2(5) . . ? C6 C5 C4 118.9(6) . . ? C6 C5 C13 117.5(5) . . ? C4 C5 C13 123.5(6) . . ? C1 C6 C5 120.3(6) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C7 S1 C4 103.8(3) . . ? C12 C7 C8 120.0(6) . . ? C12 C7 S1 124.3(5) . . ? C8 C7 S1 115.7(5) . . ? C9 C8 C7 120.6(6) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 119.0(6) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C11 122.6(6) . . ? C9 C10 N2 120.0(6) . . ? C11 C10 N2 117.4(6) . . ? O1 N2 O2 123.6(6) . . ? O1 N2 C10 119.8(6) . . ? O2 N2 C10 116.6(7) . . ? C10 C11 C12 119.9(6) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C7 118.0(6) . . ? C11 C12 C13 118.0(6) . . ? C7 C12 C13 124.0(6) . . ? O3 C13 C5 121.4(6) . . ? O3 C13 C12 119.0(6) . . ? C5 C13 C12 119.7(5) . . ? 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 C6 C1 C2 C3 1.0(11) . . . . ? Br1 C1 C2 C3 -177.4(5) . . . . ? C1 C2 C3 C4 -0.6(10) . . . . ? C2 C3 C4 C5 -0.6(10) . . . . ? C2 C3 C4 S1 -179.4(5) . . . . ? C3 C4 C5 C6 1.4(10) . . . . ? S1 C4 C5 C6 -179.9(5) . . . . ? C3 C4 C5 C13 -178.3(6) . . . . ? S1 C4 C5 C13 0.4(9) . . . . ? C2 C1 C6 C5 -0.2(11) . . . . ? Br1 C1 C6 C5 178.2(5) . . . . ? C4 C5 C6 C1 -1.0(10) . . . . ? C13 C5 C6 C1 178.7(6) . . . . ? C3 C4 S1 C7 -176.3(5) . . . . ? C5 C4 S1 C7 4.9(7) . . . . ? C4 S1 C7 C12 -4.5(7) . . . . ? C4 S1 C7 C8 174.6(5) . . . . ? C12 C7 C8 C9 -0.6(10) . . . . ? S1 C7 C8 C9 -179.8(5) . . . . ? C7 C8 C9 C10 0.7(11) . . . . ? C8 C9 C10 C11 -0.8(11) . . . . ? C8 C9 C10 N2 -178.6(6) . . . . ? C9 C10 N2 O1 179.0(7) . . . . ? C11 C10 N2 O1 1.1(10) . . . . ? C9 C10 N2 O2 0.6(10) . . . . ? C11 C10 N2 O2 -177.2(7) . . . . ? C9 C10 C11 C12 0.8(10) . . . . ? N2 C10 C11 C12 178.6(6) . . . . ? C10 C11 C12 C7 -0.7(9) . . . . ? C10 C11 C12 C13 -180.0(6) . . . . ? C8 C7 C12 C11 0.6(9) . . . . ? S1 C7 C12 C11 179.7(5) . . . . ? C8 C7 C12 C13 179.8(6) . . . . ? S1 C7 C12 C13 -1.1(10) . . . . ? C6 C5 C13 O3 -6.1(11) . . . . ? C4 C5 C13 O3 173.6(7) . . . . ? C6 C5 C13 C12 173.2(6) . . . . ? C4 C5 C13 C12 -7.1(10) . . . . ? C11 C12 C13 O3 6.1(10) . . . . ? C7 C12 C13 O3 -173.2(7) . . . . ? C11 C12 C13 C5 -173.3(6) . . . . ? C7 C12 C13 C5 7.5(10) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 66.92 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.877 _refine_diff_density_min -0.890 _refine_diff_density_rms 0.171 #END data_compound4 _database_code_depnum_ccdc_archive 'CCDC 798534' #TrackingRef '- compound 1_4and6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 N2 O3 S' _chemical_formula_weight 272.27 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.665(3) _cell_length_b 19.245(7) _cell_length_c 8.027(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.656(14) _cell_angle_gamma 90.00 _cell_volume 1167.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2194 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 27.64 _exptl_crystal_description plate _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9457 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9608 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 27.83 _reflns_number_total 2727 _reflns_number_gt 1999 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2727 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 N1 N 0.4081(2) 0.30470(9) 0.6382(2) 0.0353(4) Uani 1 1 d . . . H1A H 0.5100(18) 0.3201(3) 0.6288(3) 0.042 Uiso 1 1 calc R . . H1B H 0.3389(12) 0.3291(5) 0.6867(9) 0.042 Uiso 1 1 calc R . . C1 C 0.3554(2) 0.24048(9) 0.5752(2) 0.0246(4) Uani 1 1 d . . . C2 C 0.1854(2) 0.21438(9) 0.5882(2) 0.0252(4) Uani 1 1 d . . . H2 H 0.1104 0.2406 0.6432 0.030 Uiso 1 1 calc R . . C3 C 0.1293(2) 0.15078(9) 0.5207(2) 0.0238(4) Uani 1 1 d . . . H3 H 0.0166 0.1349 0.5294 0.029 Uiso 1 1 calc R . . C4 C 0.2410(2) 0.10943(9) 0.4383(2) 0.0206(4) Uani 1 1 d . . . C5 C 0.4122(2) 0.13387(9) 0.4269(2) 0.0203(4) Uani 1 1 d . . . C6 C 0.4666(2) 0.19918(9) 0.4948(2) 0.0238(4) Uani 1 1 d . . . H6 H 0.5791 0.2153 0.4862 0.029 Uiso 1 1 calc R . . S1 S 0.15291(5) 0.03021(2) 0.35617(6) 0.02416(13) Uani 1 1 d . . . C7 C 0.3262(2) -0.00779(9) 0.2742(2) 0.0215(4) Uani 1 1 d . . . C8 C 0.2910(2) -0.07424(9) 0.2007(2) 0.0251(4) Uani 1 1 d . . . H8 H 0.1805 -0.0945 0.1982 0.030 Uiso 1 1 calc R . . C9 C 0.4198(2) -0.10913(9) 0.1330(2) 0.0261(4) Uani 1 1 d . . . H9 H 0.3973 -0.1529 0.0850 0.031 Uiso 1 1 calc R . . C10 C 0.5845(2) -0.07752(9) 0.1376(2) 0.0212(4) Uani 1 1 d . . . N2 N 0.72141(19) -0.11386(8) 0.06216(19) 0.0267(3) Uani 1 1 d . . . O1 O 0.86753(17) -0.08691(7) 0.07135(19) 0.0385(4) Uani 1 1 d . . . O2 O 0.68196(18) -0.17000(7) -0.00933(18) 0.0400(4) Uani 1 1 d . . . C11 C 0.6239(2) -0.01301(9) 0.2079(2) 0.0215(4) Uani 1 1 d . . . H11 H 0.7352 0.0064 0.2091 0.026 Uiso 1 1 calc R . . C12 C 0.4935(2) 0.02344(8) 0.2781(2) 0.0193(3) Uani 1 1 d . . . C13 C 0.5427(2) 0.09332(9) 0.3496(2) 0.0206(4) Uani 1 1 d . . . O3 O 0.69134(16) 0.11678(7) 0.34514(17) 0.0308(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0296(8) 0.0342(9) 0.0438(11) -0.0112(8) 0.0115(8) -0.0015(7) C1 0.0259(9) 0.0274(9) 0.0196(9) 0.0014(7) 0.0015(7) 0.0040(7) C2 0.0243(9) 0.0319(10) 0.0204(10) 0.0035(7) 0.0062(7) 0.0084(7) C3 0.0185(8) 0.0331(10) 0.0202(10) 0.0055(7) 0.0046(7) 0.0032(7) C4 0.0183(8) 0.0258(9) 0.0179(9) 0.0049(7) 0.0034(7) 0.0025(6) C5 0.0180(8) 0.0251(9) 0.0180(9) 0.0040(7) 0.0036(7) 0.0013(6) C6 0.0199(8) 0.0286(9) 0.0231(10) 0.0025(7) 0.0045(7) -0.0010(7) S1 0.0146(2) 0.0303(2) 0.0288(3) -0.00128(19) 0.00748(17) -0.00186(17) C7 0.0168(8) 0.0294(9) 0.0184(9) 0.0041(7) 0.0029(6) 0.0019(7) C8 0.0173(8) 0.0314(10) 0.0261(10) -0.0016(8) 0.0020(7) -0.0042(7) C9 0.0239(9) 0.0293(10) 0.0240(10) -0.0024(8) 0.0012(7) -0.0006(7) C10 0.0188(8) 0.0287(9) 0.0160(9) 0.0018(7) 0.0022(7) 0.0063(7) N2 0.0218(8) 0.0359(9) 0.0218(8) 0.0014(7) 0.0019(6) 0.0093(6) O1 0.0238(7) 0.0473(9) 0.0468(9) -0.0051(7) 0.0131(6) 0.0041(6) O2 0.0363(8) 0.0432(8) 0.0398(9) -0.0170(7) 0.0041(7) 0.0071(7) C11 0.0158(7) 0.0301(9) 0.0187(9) 0.0054(7) 0.0033(7) 0.0021(7) C12 0.0150(7) 0.0265(9) 0.0165(8) 0.0048(7) 0.0032(6) 0.0016(6) C13 0.0174(8) 0.0271(9) 0.0177(9) 0.0031(7) 0.0044(7) -0.0005(6) O3 0.0197(6) 0.0312(7) 0.0441(9) -0.0032(6) 0.0129(6) -0.0048(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.370(2) . ? N1 H1A 0.8505 . ? N1 H1B 0.8505 . ? C1 C6 1.400(2) . ? C1 C2 1.416(2) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.411(2) . ? C3 H3 0.9300 . ? C4 C5 1.412(2) . ? C4 S1 1.7510(19) . ? C5 C6 1.405(2) . ? C5 C13 1.484(2) . ? C6 H6 0.9300 . ? S1 C7 1.7395(17) . ? C7 C12 1.412(2) . ? C7 C8 1.415(2) . ? C8 C9 1.379(2) . ? C8 H8 0.9300 . ? C9 C10 1.397(2) . ? C9 H9 0.9300 . ? C10 C11 1.376(2) . ? C10 N2 1.473(2) . ? N2 O1 1.225(2) . ? N2 O2 1.237(2) . ? C11 C12 1.413(2) . ? C11 H11 0.9300 . ? C12 C13 1.486(2) . ? C13 O3 1.232(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? N1 C1 C6 121.15(17) . . ? N1 C1 C2 120.73(16) . . ? C6 C1 C2 118.12(16) . . ? C3 C2 C1 121.10(16) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.74(16) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.09(16) . . ? C3 C4 S1 116.19(13) . . ? C5 C4 S1 124.72(13) . . ? C6 C5 C4 119.42(15) . . ? C6 C5 C13 117.13(15) . . ? C4 C5 C13 123.43(15) . . ? C1 C6 C5 121.52(16) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C7 S1 C4 103.76(8) . . ? C12 C7 C8 120.20(15) . . ? C12 C7 S1 124.13(14) . . ? C8 C7 S1 115.67(12) . . ? C9 C8 C7 120.37(16) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 118.76(17) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 122.61(15) . . ? C11 C10 N2 118.34(15) . . ? C9 C10 N2 119.04(16) . . ? O1 N2 O2 123.21(15) . . ? O1 N2 C10 118.76(15) . . ? O2 N2 C10 118.03(15) . . ? C10 C11 C12 119.36(15) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C7 C12 C11 118.70(16) . . ? C7 C12 C13 124.37(15) . . ? C11 C12 C13 116.93(14) . . ? O3 C13 C5 120.71(16) . . ? O3 C13 C12 119.78(15) . . ? C5 C13 C12 119.51(14) . . ? 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 N1 C1 C2 C3 178.00(16) . . . . ? C6 C1 C2 C3 -1.3(3) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C2 C3 C4 S1 -179.33(13) . . . . ? C3 C4 C5 C6 -1.1(2) . . . . ? S1 C4 C5 C6 178.62(13) . . . . ? C3 C4 C5 C13 177.36(16) . . . . ? S1 C4 C5 C13 -2.9(2) . . . . ? N1 C1 C6 C5 -178.71(16) . . . . ? C2 C1 C6 C5 0.6(3) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C13 C5 C6 C1 -177.98(16) . . . . ? C3 C4 S1 C7 -177.47(13) . . . . ? C5 C4 S1 C7 2.76(17) . . . . ? C4 S1 C7 C12 -0.77(17) . . . . ? C4 S1 C7 C8 179.05(13) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? S1 C7 C8 C9 -179.61(14) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 0.3(3) . . . . ? C8 C9 C10 N2 -178.71(16) . . . . ? C11 C10 N2 O1 3.2(2) . . . . ? C9 C10 N2 O1 -177.70(16) . . . . ? C11 C10 N2 O2 -175.94(15) . . . . ? C9 C10 N2 O2 3.1(2) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? N2 C10 C11 C12 178.78(14) . . . . ? C8 C7 C12 C11 -0.1(3) . . . . ? S1 C7 C12 C11 179.66(13) . . . . ? C8 C7 C12 C13 178.97(16) . . . . ? S1 C7 C12 C13 -1.2(2) . . . . ? C10 C11 C12 C7 0.2(2) . . . . ? C10 C11 C12 C13 -179.03(15) . . . . ? C6 C5 C13 O3 -0.4(2) . . . . ? C4 C5 C13 O3 -178.94(16) . . . . ? C6 C5 C13 C12 179.08(15) . . . . ? C4 C5 C13 C12 0.5(2) . . . . ? C7 C12 C13 O3 -178.94(16) . . . . ? C11 C12 C13 O3 0.2(2) . . . . ? C7 C12 C13 C5 1.6(3) . . . . ? C11 C12 C13 C5 -179.29(14) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.269 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.054 #END data_compound6 _database_code_depnum_ccdc_archive 'CCDC 798535' #TrackingRef '- compound 1_4and6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H7 N O3 S' _chemical_formula_weight 281.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2392(11) _cell_length_b 7.256(2) _cell_length_c 12.9183(16) _cell_angle_alpha 73.904(17) _cell_angle_beta 77.067(11) _cell_angle_gamma 70.673(18) _cell_volume 608.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 5.90 _cell_measurement_theta_max 10.01 _exptl_crystal_description plate _exptl_crystal_colour ? _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.3429 _exptl_absorpt_correction_T_max 0.9218 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2537 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0982 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.01 _reflns_number_total 2537 _reflns_number_gt 1352 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2537 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1438 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 C15 C -0.4954(7) 0.0424(7) 0.8312(4) 0.0687(15) Uani 1 1 d . . . H15 H -0.5995 0.0161 0.8842 0.082 Uiso 1 1 calc R . . C14 C -0.3681(6) 0.0745(6) 0.7665(3) 0.0480(10) Uani 1 1 d . . . C1 C -0.2062(6) 0.1175(5) 0.6842(3) 0.0369(9) Uani 1 1 d . . . C2 C -0.0133(6) 0.0487(5) 0.7109(3) 0.0428(10) Uani 1 1 d . . . H2 H 0.0085 -0.0243 0.7809 0.051 Uiso 1 1 calc R . . C3 C 0.1416(6) 0.0872(5) 0.6361(3) 0.0408(9) Uani 1 1 d . . . H3 H 0.2681 0.0407 0.6554 0.049 Uiso 1 1 calc R . . C4 C 0.1131(5) 0.1959(5) 0.5306(3) 0.0317(8) Uani 1 1 d . . . C5 C -0.0784(5) 0.2660(5) 0.5012(3) 0.0333(8) Uani 1 1 d . . . C6 C -0.2349(5) 0.2257(6) 0.5799(3) 0.0373(9) Uani 1 1 d . . . H6 H -0.3621 0.2731 0.5617 0.045 Uiso 1 1 calc R . . S1 S 0.32271(14) 0.23904(15) 0.44352(9) 0.0398(3) Uani 1 1 d . . . C7 C 0.2373(5) 0.3754(5) 0.3223(3) 0.0354(8) Uani 1 1 d . . . C8 C 0.3789(6) 0.4316(6) 0.2367(3) 0.0431(10) Uani 1 1 d . . . H8 H 0.5102 0.3946 0.2475 0.052 Uiso 1 1 calc R . . C9 C 0.3267(6) 0.5393(6) 0.1385(3) 0.0433(10) Uani 1 1 d . . . H9 H 0.4206 0.5795 0.0825 0.052 Uiso 1 1 calc R . . C10 C 0.1314(6) 0.5888(6) 0.1224(3) 0.0431(10) Uani 1 1 d . . . N2 N 0.0780(6) 0.7030(6) 0.0157(3) 0.0604(10) Uani 1 1 d . . . O1 O -0.0933(5) 0.7519(6) 0.0021(3) 0.0962(14) Uani 1 1 d . . . O2 O 0.2088(6) 0.7402(6) -0.0577(3) 0.0963(14) Uani 1 1 d . . . C11 C -0.0094(6) 0.5365(6) 0.2030(3) 0.0408(9) Uani 1 1 d . . . H11 H -0.1394 0.5728 0.1901 0.049 Uiso 1 1 calc R . . C12 C 0.0399(5) 0.4283(5) 0.3057(3) 0.0335(8) Uani 1 1 d . . . C13 C -0.1212(5) 0.3799(5) 0.3914(3) 0.0368(9) Uani 1 1 d . . . O3 O -0.2909(4) 0.4337(5) 0.3707(2) 0.0576(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C15 0.066(3) 0.056(3) 0.077(4) -0.008(3) 0.012(3) -0.029(2) C14 0.055(3) 0.041(2) 0.044(2) -0.0069(19) 0.002(2) -0.018(2) C1 0.049(2) 0.0261(19) 0.039(2) -0.0075(16) -0.0006(18) -0.0189(17) C2 0.058(3) 0.029(2) 0.035(2) -0.0010(17) -0.0057(19) -0.0093(18) C3 0.039(2) 0.034(2) 0.049(2) -0.0036(18) -0.0153(18) -0.0099(17) C4 0.0339(19) 0.0268(18) 0.0325(19) -0.0035(15) -0.0024(16) -0.0105(15) C5 0.0366(19) 0.0274(18) 0.040(2) -0.0105(16) -0.0032(17) -0.0142(15) C6 0.0357(19) 0.039(2) 0.041(2) -0.0089(17) -0.0047(17) -0.0163(16) S1 0.0326(5) 0.0403(5) 0.0451(6) -0.0049(4) -0.0079(4) -0.0109(4) C7 0.040(2) 0.0284(19) 0.038(2) -0.0065(16) -0.0042(17) -0.0118(16) C8 0.037(2) 0.048(2) 0.047(2) -0.0129(19) -0.0014(18) -0.0174(18) C9 0.050(2) 0.051(2) 0.036(2) -0.0096(18) -0.0008(18) -0.026(2) C10 0.053(2) 0.041(2) 0.034(2) -0.0090(18) -0.0031(19) -0.0136(19) N2 0.064(3) 0.071(3) 0.039(2) 0.0005(19) -0.0115(19) -0.017(2) O1 0.060(2) 0.132(4) 0.065(2) 0.015(2) -0.0196(19) -0.011(2) O2 0.087(3) 0.136(4) 0.045(2) 0.023(2) -0.0009(19) -0.046(2) C11 0.038(2) 0.046(2) 0.036(2) -0.0033(18) -0.0076(17) -0.0126(18) C12 0.0335(19) 0.0327(19) 0.037(2) -0.0100(16) -0.0067(16) -0.0102(15) C13 0.040(2) 0.0291(19) 0.043(2) -0.0064(17) -0.0088(18) -0.0128(16) O3 0.0346(15) 0.076(2) 0.0553(19) 0.0089(16) -0.0140(14) -0.0218(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C15 C14 1.137(5) . ? C15 H15 0.9300 . ? C14 C1 1.450(5) . ? C1 C6 1.380(5) . ? C1 C2 1.406(5) . ? C2 C3 1.358(5) . ? C2 H2 0.9300 . ? C3 C4 1.394(5) . ? C3 H3 0.9300 . ? C4 C5 1.409(5) . ? C4 S1 1.738(3) . ? C5 C6 1.394(5) . ? C5 C13 1.472(5) . ? C6 H6 0.9300 . ? S1 C7 1.727(4) . ? C7 C12 1.401(5) . ? C7 C8 1.399(5) . ? C8 C9 1.354(5) . ? C8 H8 0.9300 . ? C9 C10 1.388(5) . ? C9 H9 0.9300 . ? C10 C11 1.353(5) . ? C10 N2 1.459(5) . ? N2 O1 1.211(5) . ? N2 O2 1.222(4) . ? C11 C12 1.397(5) . ? C11 H11 0.9300 . ? C12 C13 1.479(5) . ? C13 O3 1.227(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 C15 H15 180.0 . . ? C15 C14 C1 179.4(5) . . ? C6 C1 C2 118.5(3) . . ? C6 C1 C14 122.2(4) . . ? C2 C1 C14 119.4(4) . . ? C3 C2 C1 120.9(4) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 S1 116.1(3) . . ? C5 C4 S1 124.2(3) . . ? C6 C5 C4 118.4(3) . . ? C6 C5 C13 118.4(3) . . ? C4 C5 C13 123.2(3) . . ? C1 C6 C5 121.8(4) . . ? C1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C7 S1 C4 104.37(17) . . ? C12 C7 C8 119.7(4) . . ? C12 C7 S1 124.1(3) . . ? C8 C7 S1 116.2(3) . . ? C9 C8 C7 120.7(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 119.2(4) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 121.7(4) . . ? C11 C10 N2 119.8(4) . . ? C9 C10 N2 118.5(4) . . ? O1 N2 O2 122.3(4) . . ? O1 N2 C10 118.8(4) . . ? O2 N2 C10 118.8(4) . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 118.4(3) . . ? C11 C12 C13 117.8(3) . . ? C7 C12 C13 123.8(3) . . ? O3 C13 C5 119.9(3) . . ? O3 C13 C12 119.9(3) . . ? C5 C13 C12 120.2(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 C15 C14 C1 C6 -87(50) . . . . ? C15 C14 C1 C2 92(50) . . . . ? C6 C1 C2 C3 -0.1(6) . . . . ? C14 C1 C2 C3 -179.6(4) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C2 C3 C4 S1 178.8(3) . . . . ? C3 C4 C5 C6 0.7(5) . . . . ? S1 C4 C5 C6 -178.2(3) . . . . ? C3 C4 C5 C13 -179.3(4) . . . . ? S1 C4 C5 C13 1.8(5) . . . . ? C2 C1 C6 C5 0.7(5) . . . . ? C14 C1 C6 C5 -179.8(3) . . . . ? C4 C5 C6 C1 -1.0(5) . . . . ? C13 C5 C6 C1 179.1(3) . . . . ? C3 C4 S1 C7 -179.8(3) . . . . ? C5 C4 S1 C7 -0.9(3) . . . . ? C4 S1 C7 C12 -1.1(4) . . . . ? C4 S1 C7 C8 179.7(3) . . . . ? C12 C7 C8 C9 1.0(6) . . . . ? S1 C7 C8 C9 -179.8(3) . . . . ? C7 C8 C9 C10 -1.8(6) . . . . ? C8 C9 C10 C11 1.6(6) . . . . ? C8 C9 C10 N2 -179.4(4) . . . . ? C11 C10 N2 O1 1.2(7) . . . . ? C9 C10 N2 O1 -177.8(4) . . . . ? C11 C10 N2 O2 -176.4(4) . . . . ? C9 C10 N2 O2 4.6(6) . . . . ? C9 C10 C11 C12 -0.6(6) . . . . ? N2 C10 C11 C12 -179.6(4) . . . . ? C10 C11 C12 C7 -0.2(6) . . . . ? C10 C11 C12 C13 178.5(3) . . . . ? C8 C7 C12 C11 0.1(5) . . . . ? S1 C7 C12 C11 -179.1(3) . . . . ? C8 C7 C12 C13 -178.6(3) . . . . ? S1 C7 C12 C13 2.3(5) . . . . ? C6 C5 C13 O3 -1.3(5) . . . . ? C4 C5 C13 O3 178.7(3) . . . . ? C6 C5 C13 C12 179.2(3) . . . . ? C4 C5 C13 C12 -0.7(5) . . . . ? C11 C12 C13 O3 0.5(5) . . . . ? C7 C12 C13 O3 179.2(4) . . . . ? C11 C12 C13 C5 179.9(3) . . . . ? C7 C12 C13 C5 -1.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.279 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.062