Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Alonso-Chamarro, Julian' 'Estevez-Hernandez, Osvaldo' 'Otazo-Sanchez, Elena M.' 'Perez-Marin, Leonel' 'Rojas-Limas, Susana' _publ_contact_author_name 'Dr Elena M Otazo-Sanchez' _publ_contact_author_address ; Dr Elena M Otazo-Sanchez Unida D Universitaria Km. 6.5 Carretera Pachuca-Tulancingo Pachuca Hidalgo MEXICO ; _publ_contact_author_email 'ELENAOTAZO@YAHOO.COM' data_srlf18 _database_code_CSD 160086 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N2 O2 S' _chemical_formula_weight 336.40 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.792(3) _cell_length_b 8.8111(17) _cell_length_c 31.303(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3528.4(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17039 _diffrn_reflns_av_R_equivalents 0.3416 _diffrn_reflns_av_sigmaI/netI 0.1780 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 23.46 _reflns_number_total 2569 _reflns_number_gt 1200 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1186P)^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 SHELXL _refine_ls_extinction_coef 0.0051(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2569 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1450 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.2535 _refine_ls_wR_factor_gt 0.1802 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 S1 S 0.64189(16) 0.10255(17) 0.62143(4) 0.0780(7) Uani 1 1 d . . . O1 O 0.9183(4) 0.2696(4) 0.50703(11) 0.0816(13) Uani 1 1 d . . . N2 N 0.8453(5) 0.0787(4) 0.64005(13) 0.0680(14) Uani 1 1 d . . . C14 C 0.9537(6) 0.1025(6) 0.63222(15) 0.0651(16) Uani 1 1 d . . . N1 N 0.8107(5) 0.2003(5) 0.57757(13) 0.0686(15) Uani 1 1 d . . . O2 O 0.6751(4) 0.3567(4) 0.55556(11) 0.0808(13) Uani 1 1 d . . . C4 C 0.8274(6) 0.3420(6) 0.51375(15) 0.0673(16) Uani 1 1 d . . . C8 C 0.8466(5) 0.0531(5) 0.71908(16) 0.0655(17) Uani 1 1 d . . . C5 C 0.7602(6) 0.3008(6) 0.55047(15) 0.0642(16) Uani 1 1 d . . . C6 C 0.7678(6) 0.1285(5) 0.61387(15) 0.0711(19) Uani 1 1 d . . . C7 C 0.8205(6) -0.0211(6) 0.67681(15) 0.080(2) Uani 1 1 d . . . H7A H 0.8596 -0.1149 0.6742 0.095 Uiso 1 1 calc R . . H7B H 0.7467 -0.0461 0.6763 0.095 Uiso 1 1 calc R . . C19 C 1.0131(7) -0.0097(7) 0.61334(17) 0.0785(19) Uani 1 1 d . . . H19 H 0.9826 -0.1007 0.6049 0.094 Uiso 1 1 calc R . . C3 C 0.8111(7) 0.4464(7) 0.48266(18) 0.095(2) Uani 1 1 d . . . H3 H 0.7537 0.5100 0.4795 0.114 Uiso 1 1 calc R . . C9 C 0.7822(7) 0.1615(7) 0.73583(17) 0.100(3) Uani 1 1 d . . . H9 H 0.7225 0.1901 0.7209 0.120 Uiso 1 1 calc R . . C13 C 0.9351(7) 0.0166(7) 0.74123(19) 0.090(2) Uani 1 1 d . . . H13 H 0.9812 -0.0548 0.7301 0.108 Uiso 1 1 calc R . . C16 C 1.1038(8) 0.2593(8) 0.6382(2) 0.095(2) Uani 1 1 d . . . H16 H 1.1352 0.3497 0.6466 0.114 Uiso 1 1 calc R . . C18 C 1.1164(8) 0.0148(8) 0.6074(2) 0.097(2) Uani 1 1 d . . . H18 H 1.1570 -0.0607 0.5949 0.116 Uiso 1 1 calc R . . C2 C 0.9003(7) 0.4379(8) 0.4560(2) 0.104(3) Uani 1 1 d . . . H2 H 0.9129 0.4971 0.4320 0.125 Uiso 1 1 calc R . . C15 C 1.0006(7) 0.2383(7) 0.64484(19) 0.085(2) Uani 1 1 d . . . H15 H 0.9610 0.3139 0.6577 0.102 Uiso 1 1 calc R . . C17 C 1.1624(7) 0.1488(9) 0.6193(2) 0.099(2) Uani 1 1 d . . . H17 H 1.2334 0.1644 0.6145 0.119 Uiso 1 1 calc R . . C1 C 0.9620(7) 0.3320(8) 0.47110(18) 0.094(2) Uani 1 1 d . . . H1 H 1.0257 0.3036 0.4592 0.113 Uiso 1 1 calc R . . C12 C 0.9571(8) 0.0849(9) 0.7802(2) 0.106(3) Uani 1 1 d . . . H12 H 1.0175 0.0592 0.7951 0.128 Uiso 1 1 calc R . . C11 C 0.8895(9) 0.1902(10) 0.7966(2) 0.119(3) Uani 1 1 d . . . H11 H 0.9030 0.2344 0.8230 0.143 Uiso 1 1 calc R . . C10 C 0.8046(9) 0.2293(9) 0.7747(2) 0.126(4) Uani 1 1 d . . . H10 H 0.7598 0.3028 0.7856 0.152 Uiso 1 1 calc R . . H100 H 0.884(5) 0.177(5) 0.5670(16) 0.072(17) 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 S1 0.0805(17) 0.0807(10) 0.0727(10) 0.0002(7) 0.0071(9) -0.0058(8) O1 0.083(4) 0.093(3) 0.068(2) -0.0003(19) 0.013(2) 0.012(2) N2 0.086(5) 0.068(3) 0.049(2) 0.0002(19) -0.002(3) -0.009(3) C14 0.071(5) 0.068(3) 0.057(3) 0.002(2) -0.011(3) 0.004(3) N1 0.081(5) 0.073(3) 0.052(2) 0.004(2) 0.005(3) 0.006(3) O2 0.085(4) 0.079(2) 0.078(2) 0.0011(19) 0.006(2) 0.014(2) C4 0.078(5) 0.071(3) 0.053(3) -0.004(2) 0.000(3) 0.000(3) C8 0.078(5) 0.060(3) 0.058(3) 0.012(2) 0.002(3) -0.001(3) C5 0.078(5) 0.058(3) 0.056(3) -0.010(2) -0.001(3) 0.005(3) C6 0.106(6) 0.060(3) 0.047(3) -0.011(2) -0.005(3) -0.009(3) C7 0.114(7) 0.062(3) 0.062(3) 0.002(2) -0.002(3) -0.005(3) C19 0.075(6) 0.079(4) 0.081(4) 0.002(3) 0.002(4) 0.007(4) C3 0.117(8) 0.095(4) 0.073(4) 0.017(3) -0.003(4) 0.010(4) C9 0.133(8) 0.105(4) 0.062(3) 0.010(3) 0.001(4) 0.024(5) C13 0.102(7) 0.089(4) 0.080(4) 0.009(3) -0.011(4) 0.001(4) C16 0.107(8) 0.080(4) 0.098(5) -0.003(3) -0.014(5) -0.012(5) C18 0.109(8) 0.086(5) 0.095(4) 0.001(3) 0.005(5) 0.016(5) C2 0.129(8) 0.122(6) 0.063(4) 0.016(4) 0.012(5) -0.014(5) C15 0.096(7) 0.078(4) 0.080(4) -0.002(3) 0.001(4) 0.003(4) C17 0.082(7) 0.108(6) 0.106(5) 0.013(4) -0.010(5) -0.009(5) C1 0.108(7) 0.113(5) 0.061(3) -0.006(3) 0.023(4) -0.001(5) C12 0.120(8) 0.126(6) 0.073(4) 0.024(4) -0.021(5) -0.020(5) C11 0.184(11) 0.120(6) 0.054(4) 0.003(4) -0.005(5) -0.041(7) C10 0.196(12) 0.116(6) 0.068(4) -0.009(4) 0.033(6) 0.015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.644(8) . ? O1 C4 1.343(8) . ? O1 C1 1.372(7) . ? N2 C6 1.358(8) . ? N2 C14 1.424(8) . ? N2 C7 1.482(6) . ? C14 C19 1.380(8) . ? C14 C15 1.396(8) . ? N1 C5 1.387(7) . ? N1 C6 1.412(7) . ? O2 C5 1.205(7) . ? C4 C3 1.355(7) . ? C4 C5 1.481(8) . ? C8 C9 1.366(8) . ? C8 C13 1.366(9) . ? C8 C7 1.513(7) . ? C19 C18 1.351(10) . ? C3 C2 1.415(10) . ? C9 C10 1.386(9) . ? C13 C12 1.390(9) . ? C16 C15 1.348(10) . ? C16 C17 1.365(10) . ? C18 C17 1.372(10) . ? C2 C1 1.310(10) . ? C12 C11 1.368(12) . ? C11 C10 1.329(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C1 106.9(5) . . ? C6 N2 C14 124.0(5) . . ? C6 N2 C7 120.3(6) . . ? C14 N2 C7 115.4(5) . . ? C19 C14 C15 119.9(7) . . ? C19 C14 N2 120.3(6) . . ? C15 C14 N2 119.8(6) . . ? C5 N1 C6 126.7(6) . . ? O1 C4 C3 110.1(6) . . ? O1 C4 C5 120.5(5) . . ? C3 C4 C5 129.4(7) . . ? C9 C8 C13 118.1(6) . . ? C9 C8 C7 120.3(6) . . ? C13 C8 C7 121.7(6) . . ? O2 C5 N1 126.9(6) . . ? O2 C5 C4 121.8(5) . . ? N1 C5 C4 111.2(6) . . ? N2 C6 N1 110.3(6) . . ? N2 C6 S1 125.7(4) . . ? N1 C6 S1 124.0(5) . . ? N2 C7 C8 112.0(4) . . ? C18 C19 C14 118.9(7) . . ? C4 C3 C2 105.3(7) . . ? C8 C9 C10 120.9(8) . . ? C8 C13 C12 120.7(7) . . ? C15 C16 C17 120.5(7) . . ? C19 C18 C17 121.3(7) . . ? C1 C2 C3 108.1(6) . . ? C16 C15 C14 119.7(7) . . ? C16 C17 C18 119.7(9) . . ? C2 C1 O1 109.6(7) . . ? C11 C12 C13 119.7(8) . . ? C10 C11 C12 120.0(7) . . ? C11 C10 C9 120.6(8) . . ? 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 N2 C14 C19 -97.5(6) . . . . ? C7 N2 C14 C19 75.8(6) . . . . ? C6 N2 C14 C15 84.4(6) . . . . ? C7 N2 C14 C15 -102.3(5) . . . . ? C1 O1 C4 C3 1.3(7) . . . . ? C1 O1 C4 C5 179.9(5) . . . . ? C6 N1 C5 O2 8.5(9) . . . . ? C6 N1 C5 C4 -175.0(4) . . . . ? O1 C4 C5 O2 -174.8(5) . . . . ? C3 C4 C5 O2 3.6(9) . . . . ? O1 C4 C5 N1 8.4(7) . . . . ? C3 C4 C5 N1 -173.2(6) . . . . ? C14 N2 C6 N1 2.4(6) . . . . ? C7 N2 C6 N1 -170.5(4) . . . . ? C14 N2 C6 S1 179.5(4) . . . . ? C7 N2 C6 S1 6.6(6) . . . . ? C5 N1 C6 N2 -160.4(5) . . . . ? C5 N1 C6 S1 22.5(7) . . . . ? C6 N2 C7 C8 -116.7(6) . . . . ? C14 N2 C7 C8 69.8(6) . . . . ? C9 C8 C7 N2 77.2(8) . . . . ? C13 C8 C7 N2 -101.7(7) . . . . ? C15 C14 C19 C18 -0.2(8) . . . . ? N2 C14 C19 C18 -178.3(5) . . . . ? O1 C4 C3 C2 -1.5(7) . . . . ? C5 C4 C3 C2 180.0(6) . . . . ? C13 C8 C9 C10 -1.7(10) . . . . ? C7 C8 C9 C10 179.3(6) . . . . ? C9 C8 C13 C12 1.8(9) . . . . ? C7 C8 C13 C12 -179.3(6) . . . . ? C14 C19 C18 C17 -0.6(10) . . . . ? C4 C3 C2 C1 1.2(8) . . . . ? C17 C16 C15 C14 0.0(10) . . . . ? C19 C14 C15 C16 0.4(9) . . . . ? N2 C14 C15 C16 178.6(6) . . . . ? C15 C16 C17 C18 -0.8(10) . . . . ? C19 C18 C17 C16 1.1(10) . . . . ? C3 C2 C1 O1 -0.4(8) . . . . ? C4 O1 C1 C2 -0.5(7) . . . . ? C8 C13 C12 C11 -0.2(11) . . . . ? C13 C12 C11 C10 -1.6(12) . . . . ? C12 C11 C10 C9 1.6(13) . . . . ? C8 C9 C10 C11 0.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 23.46 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.290 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.077 data_otazo2m _database_code_CSD 160087 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 N2 O2 S' _chemical_formula_weight 252.33 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.3964(6) _cell_length_b 10.3444(9) _cell_length_c 34.536(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2642.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12221 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1897 _reflns_number_gt 1490 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.0044P] 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 0.0114(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1897 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.003 _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 S1 S 0.02670(7) 1.16558(5) 0.117718(15) 0.0590(2) Uani 1 1 d . . . O2 O 0.24040(17) 1.08685(11) -0.01676(3) 0.0537(4) Uani 1 1 d . . . O1 O 0.20366(17) 0.81738(11) 0.04596(4) 0.0550(4) Uani 1 1 d . . . N1 N 0.1548(2) 1.03199(15) 0.05845(4) 0.0471(4) Uani 1 1 d . . . N2 N 0.0940(2) 0.91335(16) 0.11372(5) 0.0515(4) Uani 1 1 d . . . C5 C 0.2058(2) 0.93071(17) 0.03529(5) 0.0438(4) Uani 1 1 d . . . C2 C 0.3862(2) 0.97653(19) -0.06209(5) 0.0556(5) Uani 1 1 d . . . H2 H 0.4444 0.9555 -0.0851 0.067 Uiso 1 1 calc R . . C3 C 0.3548(2) 0.89394(18) -0.03036(6) 0.0524(5) Uani 1 1 d . . . H3 H 0.3890 0.8077 -0.0283 0.063 Uiso 1 1 calc R . . C1 C 0.3163(3) 1.0904(2) -0.05260(6) 0.0585(5) Uani 1 1 d . . . H1 H 0.3189 1.1632 -0.0684 0.070 Uiso 1 1 calc R . . C6 C 0.0932(2) 1.02818(17) 0.09689(5) 0.0459(5) Uani 1 1 d . . . C4 C 0.2658(2) 0.96375(16) -0.00361(5) 0.0431(4) Uani 1 1 d . . . C8 C -0.0369(3) 0.7473(2) 0.15462(5) 0.0587(5) Uani 1 1 d . . . H8A H 0.0645 0.6907 0.1491 0.070 Uiso 1 1 calc R . . H8B H -0.1292 0.7321 0.1352 0.070 Uiso 1 1 calc R . . C7 C 0.0248(2) 0.88704(18) 0.15256(5) 0.0511(5) Uani 1 1 d . . . H7 H -0.0803 0.9427 0.1570 0.061 Uiso 1 1 calc R . . C10 C 0.0213(3) 0.7479(2) 0.22645(6) 0.0773(7) Uani 1 1 d . . . H10A H -0.0352 0.7340 0.2515 0.093 Uiso 1 1 calc R . . H10B H 0.1248 0.6907 0.2245 0.093 Uiso 1 1 calc R . . C12 C 0.1643(3) 0.9153(2) 0.18380(6) 0.0628(6) Uani 1 1 d . . . H12A H 0.2006 1.0053 0.1824 0.075 Uiso 1 1 calc R . . H12B H 0.2706 0.8621 0.1797 0.075 Uiso 1 1 calc R . . C11 C 0.0842(3) 0.8868(2) 0.22354(6) 0.0729(6) Uani 1 1 d . . . H11A H 0.1745 0.9032 0.2433 0.088 Uiso 1 1 calc R . . H11B H -0.0173 0.9441 0.2282 0.088 Uiso 1 1 calc R . . C9 C -0.1126(3) 0.7158(2) 0.19460(6) 0.0732(6) Uani 1 1 d . . . H9A H -0.2230 0.7644 0.1987 0.088 Uiso 1 1 calc R . . H9B H -0.1422 0.6245 0.1958 0.088 Uiso 1 1 calc R . . H13 H 0.138(3) 0.854(2) 0.1006(6) 0.070(7) Uiso 1 1 d . . . H14 H 0.169(2) 1.1070(19) 0.0487(5) 0.053(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 S1 0.0679(4) 0.0514(3) 0.0578(3) -0.0040(3) 0.0036(3) 0.0091(2) O2 0.0687(8) 0.0437(8) 0.0487(8) 0.0057(6) 0.0066(6) 0.0072(6) O1 0.0711(9) 0.0395(8) 0.0543(8) 0.0030(6) 0.0047(7) -0.0037(6) N1 0.0556(9) 0.0379(9) 0.0479(10) 0.0040(8) 0.0035(7) 0.0005(7) N2 0.0606(10) 0.0465(10) 0.0476(10) 0.0024(9) 0.0075(8) 0.0027(8) C5 0.0418(10) 0.0395(11) 0.0502(11) 0.0006(9) -0.0048(9) -0.0034(8) C2 0.0577(12) 0.0624(13) 0.0468(11) -0.0095(11) 0.0030(9) -0.0052(10) C3 0.0585(11) 0.0404(10) 0.0582(12) -0.0079(10) -0.0017(10) -0.0018(9) C1 0.0715(13) 0.0580(13) 0.0459(12) 0.0089(10) 0.0032(10) -0.0022(11) C6 0.0415(10) 0.0496(11) 0.0466(11) 0.0024(10) -0.0021(8) -0.0017(8) C4 0.0449(10) 0.0370(10) 0.0475(11) 0.0009(9) -0.0040(9) -0.0037(8) C8 0.0651(12) 0.0617(12) 0.0492(12) -0.0008(10) 0.0022(10) -0.0121(10) C7 0.0542(11) 0.0548(11) 0.0444(11) -0.0001(10) 0.0039(9) -0.0010(9) C10 0.0944(16) 0.0832(16) 0.0543(13) 0.0125(13) 0.0042(12) -0.0048(13) C12 0.0679(13) 0.0624(13) 0.0582(12) -0.0011(11) -0.0054(11) -0.0100(10) C11 0.0880(16) 0.0805(16) 0.0504(12) -0.0018(12) -0.0122(11) -0.0034(13) C9 0.0834(15) 0.0770(15) 0.0590(14) 0.0062(12) 0.0087(12) -0.0210(12) _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 S1 C6 1.6672(18) . ? O2 C1 1.360(2) . ? O2 C4 1.365(2) . ? O1 C5 1.2288(19) . ? N1 C5 1.371(2) . ? N1 C6 1.404(2) . ? N2 C6 1.322(2) . ? N2 C7 1.461(2) . ? C5 C4 1.456(2) . ? C2 C1 1.328(3) . ? C2 C3 1.409(3) . ? C3 C4 1.345(2) . ? C8 C7 1.517(3) . ? C8 C9 1.525(3) . ? C7 C12 1.521(3) . ? C10 C11 1.513(3) . ? C10 C9 1.517(3) . ? C12 C11 1.524(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C4 105.74(14) . . ? C5 N1 C6 128.26(16) . . ? C6 N2 C7 124.68(17) . . ? O1 C5 N1 123.42(17) . . ? O1 C5 C4 120.29(16) . . ? N1 C5 C4 116.28(15) . . ? C1 C2 C3 106.38(17) . . ? C4 C3 C2 106.82(17) . . ? C2 C1 O2 111.18(17) . . ? N2 C6 N1 116.05(16) . . ? N2 C6 S1 125.29(14) . . ? N1 C6 S1 118.66(13) . . ? C3 C4 O2 109.87(16) . . ? C3 C4 C5 131.10(16) . . ? O2 C4 C5 118.95(16) . . ? C7 C8 C9 110.89(17) . . ? N2 C7 C8 109.01(15) . . ? N2 C7 C12 112.19(16) . . ? C8 C7 C12 110.71(16) . . ? C11 C10 C9 111.15(18) . . ? C7 C12 C11 109.74(16) . . ? C10 C11 C12 111.29(18) . . ? C10 C9 C8 111.71(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.132 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.032