Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'P. Tasker' _publ_contact_author_address ; Department of Chemistry University of Edinburgh West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email P.A.TASKER@ED.AC.UK _publ_section_title ; Design of base metal extractants. Part 1. Inter-ligand hydrogen bonding in the assembly of pseudo-macrocyclic bis(aminosulfonamidato)M(II) complexes. ; loop_ _publ_author_name 'P. Tasker' 'Christopher W. Baxter' 'John Campbell' 'Leonard Lindoy' 'H. McNab' 'Andrew Parkin' ; S.Parsons ; 'Clare Squires' 'Gang Wei.' 'David J. White' # Attachment 'cs_publish.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 233475' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 N2 O2 S' _chemical_formula_sum 'C9 H14 N2 O2 S' _chemical_formula_weight 214.28 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 Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 6.4295(17) _cell_length_b 7.0606(19) _cell_length_c 22.987(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.097(5) _cell_angle_gamma 90.00 _cell_volume 1043.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2234 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _exptl_crystal_description rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX 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 5773 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.44 _reflns_number_total 3730 _reflns_number_gt 3283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All hydrogen atoms were placed in geometrically calculated positions and refined as riding groups, with the exception of those hydrogen atoms involved in hydrogen bonds, which were placed on the difference map and refined with distance restraints. The structure was determined to be twinned by a 2-fold axis parallel to the a axis and a twin law of 1 0 0 0 -1 0 0 0 -1 was applied within shelxtl. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary Patterson _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.39(10) _refine_ls_number_reflns 3730 _refine_ls_number_parameters 274 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 C1A C 0.8648(8) 0.9485(5) -0.31888(17) 0.0245(10) Uani 1 1 d . . . S2A S 0.75371(15) 0.90586(14) -0.24966(4) 0.0292(3) Uani 1 1 d . . . O1A O 0.5359(5) 0.9412(4) -0.25581(14) 0.0373(8) Uani 1 1 d . . . O2A O 0.8215(5) 0.7226(4) -0.23070(11) 0.0383(8) Uani 1 1 d . . . N3A N 0.8523(6) 1.0557(4) -0.20405(13) 0.0295(9) Uani 1 1 d D . . H3A H 0.992(4) 1.014(6) -0.1903(18) 0.035 Uiso 1 1 d D . . C4A C 0.8118(6) 1.2592(5) -0.21304(15) 0.0276(9) Uani 1 1 d . . . H4AA H 0.7720 1.2808 -0.2541 0.033 Uiso 1 1 calc R . . H4BA H 0.9409 1.3314 -0.2053 0.033 Uiso 1 1 calc R . . C5A C 0.6405(7) 1.3317(5) -0.17384(15) 0.0293(10) Uani 1 1 d . . . H5AA H 0.6176 1.4684 -0.1809 0.035 Uiso 1 1 calc R . . H5BA H 0.5092 1.2636 -0.1822 0.035 Uiso 1 1 calc R . . N6A N 0.7018(6) 1.3008(5) -0.11327(13) 0.0321(8) Uani 1 1 d D . . H6AA H 0.573(4) 1.334(5) -0.0918(16) 0.038 Uiso 1 1 d D . . H6BA H 0.715(7) 1.169(3) -0.1014(15) 0.038 Uiso 1 1 d D . . C7A C 1.0699(7) 0.8937(5) -0.32878(16) 0.0287(9) Uani 1 1 d . . . H7A H 1.1514 0.8406 -0.2984 0.034 Uiso 1 1 calc R . . C8A C 1.1516(7) 0.9180(5) -0.38332(17) 0.0337(10) Uani 1 1 d . . . H8A H 1.2903 0.8781 -0.3905 0.040 Uiso 1 1 calc R . . C9A C 1.0386(9) 0.9988(6) -0.42820(18) 0.0318(11) Uani 1 1 d . . . C10A C 0.8352(8) 1.0574(5) -0.41735(18) 0.0340(11) Uani 1 1 d . . . H10A H 0.7555 1.1137 -0.4476 0.041 Uiso 1 1 calc R . . C11A C 0.7487(7) 1.0337(5) -0.36245(15) 0.0272(9) Uani 1 1 d . . . H11A H 0.6110 1.0756 -0.3549 0.033 Uiso 1 1 calc R . . C12A C 1.1239(9) 1.0191(7) -0.48882(18) 0.0497(15) Uani 1 1 d . . . H21A H 1.0918 1.1458 -0.5037 0.075 Uiso 1 1 calc R . . H22A H 1.0605 0.9236 -0.5142 0.075 Uiso 1 1 calc R . . H23A H 1.2750 1.0010 -0.4880 0.075 Uiso 1 1 calc R . . C1B C 1.0646(8) 0.4526(5) 0.03738(18) 0.0237(10) Uani 1 1 d . . . S2B S 1.19167(14) 0.39089(13) -0.02812(4) 0.0270(3) Uani 1 1 d . . . O1B O 1.3993(5) 0.4686(4) -0.02389(13) 0.0393(8) Uani 1 1 d . . . O2B O 1.1726(6) 0.1902(4) -0.03596(12) 0.0394(8) Uani 1 1 d . . . N3B N 1.0729(7) 0.4878(4) -0.08113(14) 0.0292(9) Uani 1 1 d D . . H3B H 0.943(4) 0.427(5) -0.0936(17) 0.035 Uiso 1 1 d D . . C4B C 1.0803(7) 0.6950(5) -0.09150(17) 0.0306(10) Uani 1 1 d . . . H4AB H 1.1111 0.7609 -0.0545 0.037 Uiso 1 1 calc R . . H4BB H 0.9428 0.7389 -0.1055 0.037 Uiso 1 1 calc R . . C5B C 1.2436(7) 0.7444(5) -0.13564(18) 0.0341(10) Uani 1 1 d . . . H5AB H 1.3830 0.7143 -0.1198 0.041 Uiso 1 1 calc R . . H5BB H 1.2222 0.6677 -0.1712 0.041 Uiso 1 1 calc R . . N6B N 1.2330(6) 0.9484(4) -0.15051(13) 0.0314(8) Uani 1 1 d D . . H6AB H 1.333(5) 0.970(6) -0.1816(13) 0.038 Uiso 1 1 d D . . H6BB H 1.263(7) 1.016(5) -0.1157(11) 0.038 Uiso 1 1 d D . . C7B C 0.8592(7) 0.5132(6) 0.03620(17) 0.0299(10) Uani 1 1 d . . . H7B H 0.7852 0.5221 0.0005 0.036 Uiso 1 1 calc R . . C8B C 0.7645(7) 0.5605(5) 0.08848(15) 0.0317(9) Uani 1 1 d . . . H8B H 0.6253 0.6056 0.0884 0.038 Uiso 1 1 calc R . . C9B C 0.8703(7) 0.5427(5) 0.14058(17) 0.0280(11) Uani 1 1 d . . . C10B C 1.0733(8) 0.4779(5) 0.14079(18) 0.0283(10) Uani 1 1 d . . . H10B H 1.1454 0.4640 0.1766 0.034 Uiso 1 1 calc R . . C11B C 1.1717(7) 0.4332(5) 0.08942(15) 0.0263(9) Uani 1 1 d . . . H11B H 1.3115 0.3897 0.0897 0.032 Uiso 1 1 calc R . . C12B C 0.7629(9) 0.5931(6) 0.19780(16) 0.0411(12) Uani 1 1 d . . . H21B H 0.6118 0.5848 0.1928 0.062 Uiso 1 1 calc R . . H22B H 0.8009 0.7224 0.2092 0.062 Uiso 1 1 calc R . . H23B H 0.8073 0.5044 0.2282 0.062 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 C1A 0.026(3) 0.024(2) 0.023(2) -0.0026(17) 0.005(2) -0.002(2) S2A 0.0390(8) 0.0254(5) 0.0231(5) -0.0012(4) 0.0033(6) -0.0042(5) O1A 0.029(2) 0.0489(19) 0.0335(19) -0.0040(15) 0.0063(17) -0.0073(15) O2A 0.063(2) 0.0244(15) 0.0279(16) 0.0014(11) 0.0023(14) -0.0047(14) N3A 0.039(2) 0.0288(18) 0.0205(17) 0.0020(14) -0.0006(16) 0.0024(18) C4A 0.037(3) 0.026(2) 0.0198(19) 0.0027(16) 0.0032(18) -0.0034(17) C5A 0.040(3) 0.0170(19) 0.030(2) -0.0002(15) -0.0011(19) 0.0037(18) N6A 0.032(2) 0.0369(19) 0.0272(18) -0.0037(14) 0.0054(17) 0.0011(18) C7A 0.032(3) 0.022(2) 0.032(2) -0.0057(17) -0.0036(19) -0.0023(18) C8A 0.032(3) 0.029(2) 0.040(2) -0.0109(18) 0.004(2) -0.0028(19) C9A 0.042(3) 0.025(2) 0.028(2) -0.0116(18) 0.006(2) -0.007(2) C10A 0.044(3) 0.027(2) 0.031(2) 0.0023(18) -0.002(2) 0.001(2) C11A 0.033(3) 0.0237(18) 0.0252(18) -0.0035(16) 0.002(2) 0.0004(19) C12A 0.070(4) 0.043(3) 0.036(2) -0.0105(19) 0.017(2) -0.020(3) C1B 0.036(3) 0.0111(19) 0.024(2) 0.0003(16) 0.002(2) -0.001(2) S2B 0.0298(7) 0.0312(5) 0.0200(5) -0.0010(4) 0.0005(6) 0.0043(5) O1B 0.031(2) 0.060(2) 0.0267(17) -0.0063(16) 0.0032(17) 0.0023(17) O2B 0.059(2) 0.0324(14) 0.0274(15) -0.0012(12) 0.0032(16) 0.0100(15) N3B 0.033(3) 0.033(2) 0.0214(18) -0.0041(16) 0.0020(17) -0.0081(17) C4B 0.043(3) 0.025(2) 0.024(2) -0.0003(16) 0.0030(18) 0.000(2) C5B 0.039(3) 0.031(2) 0.032(2) 0.0022(17) 0.005(2) 0.000(2) N6B 0.036(2) 0.0300(17) 0.0284(18) -0.0004(12) 0.0047(17) -0.0019(18) C7B 0.033(3) 0.030(2) 0.027(2) 0.0015(18) -0.0029(19) 0.002(2) C8B 0.034(3) 0.024(2) 0.037(2) 0.0002(16) 0.000(2) 0.0028(18) C9B 0.040(3) 0.019(2) 0.025(2) -0.0027(17) 0.007(2) 0.001(2) C10B 0.037(3) 0.026(2) 0.0214(19) -0.0029(17) -0.007(2) -0.0064(19) C11B 0.028(2) 0.024(2) 0.0275(19) 0.0028(16) -0.0030(19) 0.0000(18) C12B 0.053(3) 0.041(2) 0.029(2) -0.0032(17) 0.003(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C11A 1.386(5) . ? C1A C7A 1.393(6) . ? C1A S2A 1.771(4) . ? S2A O1A 1.429(4) . ? S2A O2A 1.433(3) . ? S2A N3A 1.618(3) . ? N3A C4A 1.475(5) . ? N3A H3A 0.997(19) . ? C4A C5A 1.513(5) . ? C4A H4AA 0.9900 . ? C4A H4BA 0.9900 . ? C5A N6A 1.463(5) . ? C5A H5AA 0.9900 . ? C5A H5BA 0.9900 . ? N6A H6AA 0.996(19) . ? N6A H6BA 0.974(18) . ? C7A C8A 1.371(6) . ? C7A H7A 0.9500 . ? C8A C9A 1.384(6) . ? C8A H8A 0.9500 . ? C9A C10A 1.394(7) . ? C9A C12A 1.505(6) . ? C10A C11A 1.390(6) . ? C10A H10A 0.9500 . ? C11A H11A 0.9500 . ? C12A H21A 0.9800 . ? C12A H22A 0.9800 . ? C12A H23A 0.9800 . ? C1B C11B 1.386(6) . ? C1B C7B 1.389(7) . ? C1B S2B 1.769(4) . ? S2B O2B 1.433(3) . ? S2B O1B 1.446(4) . ? S2B N3B 1.592(4) . ? N3B C4B 1.483(5) . ? N3B H3B 0.978(19) . ? C4B C5B 1.503(6) . ? C4B H4AB 0.9900 . ? C4B H4BB 0.9900 . ? C5B N6B 1.482(5) . ? C5B H5AB 0.9900 . ? C5B H5BB 0.9900 . ? N6B H6AB 0.974(19) . ? N6B H6BB 0.951(18) . ? C7B C8B 1.389(5) . ? C7B H7B 0.9500 . ? C8B C9B 1.382(5) . ? C8B H8B 0.9500 . ? C9B C10B 1.383(6) . ? C9B C12B 1.528(6) . ? C10B C11B 1.377(6) . ? C10B H10B 0.9500 . ? C11B H11B 0.9500 . ? C12B H21B 0.9800 . ? C12B H22B 0.9800 . ? C12B H23B 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 C11A C1A C7A 120.8(4) . . ? C11A C1A S2A 120.4(4) . . ? C7A C1A S2A 118.9(3) . . ? O1A S2A O2A 119.03(19) . . ? O1A S2A N3A 109.4(2) . . ? O2A S2A N3A 105.94(17) . . ? O1A S2A C1A 106.1(2) . . ? O2A S2A C1A 107.7(2) . . ? N3A S2A C1A 108.23(19) . . ? C4A N3A S2A 118.5(3) . . ? C4A N3A H3A 119(2) . . ? S2A N3A H3A 112(2) . . ? N3A C4A C5A 112.0(3) . . ? N3A C4A H4AA 109.2 . . ? C5A C4A H4AA 109.2 . . ? N3A C4A H4BA 109.2 . . ? C5A C4A H4BA 109.2 . . ? H4AA C4A H4BA 107.9 . . ? N6A C5A C4A 108.7(3) . . ? N6A C5A H5AA 109.9 . . ? C4A C5A H5AA 109.9 . . ? N6A C5A H5BA 109.9 . . ? C4A C5A H5BA 109.9 . . ? H5AA C5A H5BA 108.3 . . ? C5A N6A H6AA 102(2) . . ? C5A N6A H6BA 116(2) . . ? H6AA N6A H6BA 99(3) . . ? C8A C7A C1A 118.6(4) . . ? C8A C7A H7A 120.7 . . ? C1A C7A H7A 120.7 . . ? C7A C8A C9A 122.1(5) . . ? C7A C8A H8A 119.0 . . ? C9A C8A H8A 119.0 . . ? C8A C9A C10A 118.7(4) . . ? C8A C9A C12A 122.5(5) . . ? C10A C9A C12A 118.7(5) . . ? C11A C10A C9A 120.2(4) . . ? C11A C10A H10A 119.9 . . ? C9A C10A H10A 119.9 . . ? C1A C11A C10A 119.5(4) . . ? C1A C11A H11A 120.3 . . ? C10A C11A H11A 120.3 . . ? C9A C12A H21A 109.5 . . ? C9A C12A H22A 109.5 . . ? H21A C12A H22A 109.5 . . ? C9A C12A H23A 109.5 . . ? H21A C12A H23A 109.5 . . ? H22A C12A H23A 109.5 . . ? C11B C1B C7B 121.2(4) . . ? C11B C1B S2B 118.8(4) . . ? C7B C1B S2B 120.0(3) . . ? O2B S2B O1B 117.5(2) . . ? O2B S2B N3B 106.71(18) . . ? O1B S2B N3B 109.3(2) . . ? O2B S2B C1B 108.11(18) . . ? O1B S2B C1B 106.1(2) . . ? N3B S2B C1B 108.9(2) . . ? C4B N3B S2B 122.1(3) . . ? C4B N3B H3B 114(2) . . ? S2B N3B H3B 116(2) . . ? N3B C4B C5B 111.1(3) . . ? N3B C4B H4AB 109.4 . . ? C5B C4B H4AB 109.4 . . ? N3B C4B H4BB 109.4 . . ? C5B C4B H4BB 109.4 . . ? H4AB C4B H4BB 108.0 . . ? N6B C5B C4B 110.5(3) . . ? N6B C5B H5AB 109.6 . . ? C4B C5B H5AB 109.6 . . ? N6B C5B H5BB 109.6 . . ? C4B C5B H5BB 109.6 . . ? H5AB C5B H5BB 108.1 . . ? C5B N6B H6AB 107(2) . . ? C5B N6B H6BB 107(2) . . ? H6AB N6B H6BB 114(4) . . ? C1B C7B C8B 118.4(4) . . ? C1B C7B H7B 120.8 . . ? C8B C7B H7B 120.8 . . ? C9B C8B C7B 120.8(4) . . ? C9B C8B H8B 119.6 . . ? C7B C8B H8B 119.6 . . ? C8B C9B C10B 119.7(4) . . ? C8B C9B C12B 120.2(4) . . ? C10B C9B C12B 120.1(4) . . ? C11B C10B C9B 120.5(4) . . ? C11B C10B H10B 119.7 . . ? C9B C10B H10B 119.7 . . ? C10B C11B C1B 119.3(4) . . ? C10B C11B H11B 120.3 . . ? C1B C11B H11B 120.3 . . ? C9B C12B H21B 109.5 . . ? C9B C12B H22B 109.5 . . ? H21B C12B H22B 109.5 . . ? C9B C12B H23B 109.5 . . ? H21B C12B H23B 109.5 . . ? H22B C12B H23B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.317 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.046 data_5 _database_code_depnum_ccdc_archive 'CCDC 233476' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N2 O2 S' _chemical_formula_sum 'C10 H16 N2 O2 S' _chemical_formula_weight 228.31 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 P2(1)/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 11.9460(8) _cell_length_b 7.8174(5) _cell_length_c 13.1025(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.5310(10) _cell_angle_gamma 90.00 _cell_volume 1160.16(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4625 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.5 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 6299 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2371 _reflns_number_gt 2002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All hydrogen atoms bonded to carbon atoms were placed in calculated positions and refined using a riding model, and those bonded to nitrogen were located on the difference map and refined isotropically. ; _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^)+(0.0659P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 0 _refine_ls_number_reflns 2371 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.000 _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 C1A C 0.85733(12) 0.21572(17) 0.26856(11) 0.0223(3) Uani 1 1 d . . . S2A S 0.72445(3) 0.22600(5) 0.15976(3) 0.02438(14) Uani 1 1 d . . . O1A O 0.66033(9) 0.37153(13) 0.17758(9) 0.0340(3) Uani 1 1 d . . . O2A O 0.75438(10) 0.21641(14) 0.06215(9) 0.0335(3) Uani 1 1 d . . . N3A N 0.64728(10) 0.06009(15) 0.16614(10) 0.0237(3) Uani 1 1 d . . . H3A H 0.6245(15) 0.064(2) 0.2294(14) 0.042(5) Uiso 1 1 d . . . C4A C 0.68744(12) -0.10838(19) 0.14093(11) 0.0270(3) Uani 1 1 d . . . H4A1 H 0.7442 -0.1575 0.2068 0.032 Uiso 1 1 calc R . . H4A2 H 0.7286 -0.0943 0.0867 0.032 Uiso 1 1 calc R . . C5A C 0.58430(13) -0.22973(18) 0.09788(11) 0.0259(3) Uani 1 1 d . . . H5A1 H 0.6131 -0.3373 0.0751 0.031 Uiso 1 1 calc R . . H5A2 H 0.5266 -0.1779 0.0336 0.031 Uiso 1 1 calc R . . C6A C 0.52214(14) -0.27160(18) 0.17985(12) 0.0271(3) Uani 1 1 d . . . H6A1 H 0.5821 -0.3095 0.2473 0.033 Uiso 1 1 calc R . . H6A2 H 0.4858 -0.1655 0.1961 0.033 Uiso 1 1 calc R . . N7A N 0.43045(11) -0.40359(17) 0.14609(10) 0.0273(3) Uani 1 1 d . . . H7AA H 0.4634(14) -0.502(3) 0.1245(13) 0.035(4) Uiso 1 1 d . . . H7BA H 0.3760(15) -0.373(2) 0.0876(14) 0.035(5) Uiso 1 1 d . . . C8A C 0.86221(14) 0.2929(2) 0.36498(12) 0.0298(3) Uani 1 1 d . . . H8A H 0.7967 0.3563 0.3708 0.036 Uiso 1 1 calc R . . C9A C 0.96316(14) 0.2769(2) 0.45269(13) 0.0338(4) Uani 1 1 d . . . H9A H 0.9660 0.3288 0.5190 0.041 Uiso 1 1 calc R . . C10A C 1.06050(13) 0.1865(2) 0.44572(12) 0.0289(3) Uani 1 1 d . . . C11A C 1.05384(13) 0.1107(2) 0.34805(12) 0.0303(3) Uani 1 1 d . . . H11A H 1.1197 0.0484 0.3418 0.036 Uiso 1 1 calc R . . C12A C 0.95306(12) 0.12420(19) 0.25971(11) 0.0271(3) Uani 1 1 d . . . H12A H 0.9496 0.0711 0.1935 0.033 Uiso 1 1 calc R . . C13A C 1.16862(14) 0.1670(3) 0.54286(13) 0.0418(4) Uani 1 1 d . . . H13A H 1.1872 0.2769 0.5805 0.063 Uiso 1 1 calc R . . H13B H 1.2354 0.1304 0.5199 0.063 Uiso 1 1 calc R . . H13C H 1.1536 0.0810 0.5914 0.063 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 C1A 0.0236(7) 0.0203(7) 0.0233(7) 0.0038(5) 0.0081(6) -0.0022(5) S2A 0.0243(2) 0.0240(2) 0.0250(2) 0.00604(13) 0.00804(15) 0.00029(13) O1A 0.0300(6) 0.0235(6) 0.0465(6) 0.0073(5) 0.0094(5) 0.0036(4) O2A 0.0317(6) 0.0450(7) 0.0242(5) 0.0090(5) 0.0096(5) -0.0036(5) N3A 0.0248(6) 0.0231(6) 0.0259(6) -0.0007(5) 0.0119(5) -0.0008(5) C4A 0.0281(7) 0.0255(8) 0.0297(7) -0.0020(6) 0.0126(6) 0.0011(6) C5A 0.0307(8) 0.0250(7) 0.0237(7) -0.0012(6) 0.0109(6) -0.0003(6) C6A 0.0325(8) 0.0256(8) 0.0256(7) -0.0022(6) 0.0126(6) -0.0037(6) N7A 0.0296(7) 0.0248(7) 0.0271(7) 0.0004(5) 0.0087(6) -0.0010(5) C8A 0.0284(8) 0.0327(9) 0.0315(8) -0.0044(6) 0.0138(6) 0.0005(6) C9A 0.0362(9) 0.0415(10) 0.0258(7) -0.0074(7) 0.0128(7) -0.0058(7) C10A 0.0292(8) 0.0298(8) 0.0271(7) 0.0068(6) 0.0080(6) -0.0057(6) C11A 0.0282(7) 0.0285(8) 0.0345(8) 0.0025(6) 0.0106(6) 0.0050(6) C12A 0.0306(7) 0.0265(8) 0.0263(7) -0.0018(6) 0.0118(6) 0.0017(6) C13A 0.0362(9) 0.0523(11) 0.0315(8) 0.0094(8) 0.0030(7) -0.0064(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 C1A C8A 1.384(2) . ? C1A C12A 1.385(2) . ? C1A S2A 1.7663(14) . ? S2A O1A 1.4315(11) . ? S2A O2A 1.4353(11) . ? S2A N3A 1.6087(12) . ? N3A C4A 1.4747(18) . ? N3A H3A 0.951(18) . ? C4A C5A 1.515(2) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.523(2) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A N7A 1.4670(18) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? N7A H7AA 0.945(19) . ? N7A H7BA 0.867(18) . ? C8A C9A 1.382(2) . ? C8A H8A 0.9500 . ? C9A C10A 1.388(2) . ? C9A H9A 0.9500 . ? C10A C11A 1.389(2) . ? C10A C13A 1.505(2) . ? C11A C12A 1.384(2) . ? C11A H11A 0.9500 . ? C12A H12A 0.9500 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 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 C8A C1A C12A 120.34(13) . . ? C8A C1A S2A 118.89(11) . . ? C12A C1A S2A 120.68(11) . . ? O1A S2A O2A 118.99(7) . . ? O1A S2A N3A 106.68(6) . . ? O2A S2A N3A 108.26(6) . . ? O1A S2A C1A 107.14(7) . . ? O2A S2A C1A 107.59(7) . . ? N3A S2A C1A 107.71(6) . . ? C4A N3A S2A 118.41(9) . . ? C4A N3A H3A 115.5(11) . . ? S2A N3A H3A 110.1(11) . . ? N3A C4A C5A 111.02(11) . . ? N3A C4A H4A1 109.4 . . ? C5A C4A H4A1 109.4 . . ? N3A C4A H4A2 109.4 . . ? C5A C4A H4A2 109.4 . . ? H4A1 C4A H4A2 108.0 . . ? C4A C5A C6A 113.16(12) . . ? C4A C5A H5A1 108.9 . . ? C6A C5A H5A1 108.9 . . ? C4A C5A H5A2 108.9 . . ? C6A C5A H5A2 108.9 . . ? H5A1 C5A H5A2 107.8 . . ? N7A C6A C5A 115.04(12) . . ? N7A C6A H6A1 108.5 . . ? C5A C6A H6A1 108.5 . . ? N7A C6A H6A2 108.5 . . ? C5A C6A H6A2 108.5 . . ? H6A1 C6A H6A2 107.5 . . ? C6A N7A H7AA 108.5(10) . . ? C6A N7A H7BA 110.5(12) . . ? H7AA N7A H7BA 103.1(15) . . ? C9A C8A C1A 119.48(14) . . ? C9A C8A H8A 120.3 . . ? C1A C8A H8A 120.3 . . ? C8A C9A C10A 121.27(14) . . ? C8A C9A H9A 119.4 . . ? C10A C9A H9A 119.4 . . ? C9A C10A C11A 118.28(14) . . ? C9A C10A C13A 120.48(15) . . ? C11A C10A C13A 121.21(15) . . ? C12A C11A C10A 121.19(14) . . ? C12A C11A H11A 119.4 . . ? C10A C11A H11A 119.4 . . ? C11A C12A C1A 119.45(13) . . ? C11A C12A H12A 120.3 . . ? C1A C12A H12A 120.3 . . ? C10A C13A H13A 109.5 . . ? C10A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C10A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.424 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.052 data_7 _database_code_depnum_ccdc_archive 'CCDC 233477' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H22 N2 O2 S' _chemical_formula_sum 'C17 H22 N2 O2 S' _chemical_formula_weight 318.43 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 22.113(3) _cell_length_b 8.4446(14) _cell_length_c 8.9661(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1674.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 122 _cell_measurement_theta_min 12 _cell_measurement_theta_max 16 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.89 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(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 'Stoe Stadi-4 4-circle diffractometer' _diffrn_measurement_method Omega-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 4 _diffrn_reflns_number 3525 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0884 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1770 _reflns_number_gt 1169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _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. All hydrogen atoms bonded to carbon atoms were placed in calculated positions and refined using a riding model, and those bonded to nitrogen were located on the difference map and refined isotropically. ; _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^)+(0.0413P)^2^+0.0087P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.10(17) _refine_ls_number_reflns 1770 _refine_ls_number_parameters 207 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _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 C1A C 0.3263(2) 0.7670(6) 0.3465(5) 0.0288(15) Uani 1 1 d . . . S2A S 0.36745(6) 0.94188(18) 0.31019(17) 0.0318(3) Uani 1 1 d . . . O1A O 0.32537(14) 1.0706(4) 0.3133(6) 0.0426(9) Uani 1 1 d . . . O2A O 0.40235(18) 0.9124(5) 0.1770(4) 0.0408(12) Uani 1 1 d . . . N3A N 0.41647(19) 0.9696(6) 0.4406(5) 0.0284(13) Uani 1 1 d D . . H3A H 0.4537(13) 0.906(5) 0.434(6) 0.034 Uiso 1 1 d D . . C4A C 0.3956(2) 1.0080(7) 0.5932(6) 0.0350(15) Uani 1 1 d . . . H4AA H 0.3875 0.9100 0.6483 0.042 Uiso 1 1 calc R . . H4BA H 0.3580 1.0693 0.5883 0.042 Uiso 1 1 calc R . . C5A C 0.4437(2) 1.1027(7) 0.6727(5) 0.0307(15) Uani 1 1 d . . . H5AA H 0.4505 1.2020 0.6188 0.037 Uiso 1 1 calc R . . H5BA H 0.4817 1.0429 0.6721 0.037 Uiso 1 1 calc R . . C6A C 0.4263(2) 1.1399(7) 0.8332(6) 0.0338(16) Uani 1 1 d . . . H6AA H 0.3887 1.2013 0.8344 0.041 Uiso 1 1 calc R . . H6BA H 0.4192 1.0409 0.8875 0.041 Uiso 1 1 calc R . . N7A N 0.47412(19) 1.2300(6) 0.9073(5) 0.0304(12) Uani 1 1 d D . . H7A H 0.4818(19) 1.326(4) 0.849(5) 0.036 Uiso 1 1 d D . . C8A C 0.4559(2) 1.2803(7) 1.0590(5) 0.0334(16) Uani 1 1 d . . . H8AA H 0.4372 1.1909 1.1112 0.040 Uiso 1 1 calc R . . H8BA H 0.4257 1.3651 1.0515 0.040 Uiso 1 1 calc R . . C9A C 0.5093(3) 1.3384(7) 1.1470(6) 0.0328(15) Uani 1 1 d . . . C10A C 0.5142(2) 1.2908(7) 1.2962(7) 0.0382(15) Uani 1 1 d . . . H10A H 0.4833 1.2299 1.3396 0.046 Uiso 1 1 calc R . . C11A C 0.5638(3) 1.3324(8) 1.3797(7) 0.0492(18) Uani 1 1 d . . . H11A H 0.5670 1.2985 1.4792 0.059 Uiso 1 1 calc R . . C12A C 0.6088(2) 1.4231(7) 1.3185(8) 0.0451(16) Uani 1 1 d . . . H12A H 0.6426 1.4515 1.3761 0.054 Uiso 1 1 calc R . . C13A C 0.6045(3) 1.4731(7) 1.1717(7) 0.0420(16) Uani 1 1 d . . . H13A H 0.6351 1.5361 1.1295 0.050 Uiso 1 1 calc R . . C14A C 0.5545(2) 1.4292(7) 1.0876(6) 0.0355(15) Uani 1 1 d . . . H14A H 0.5516 1.4626 0.9878 0.043 Uiso 1 1 calc R . . C15A C 0.2764(2) 0.7729(8) 0.4404(6) 0.0394(16) Uani 1 1 d . . . H15A H 0.2641 0.8694 0.4830 0.047 Uiso 1 1 calc R . . C16A C 0.2450(2) 0.6353(8) 0.4705(7) 0.0430(17) Uani 1 1 d . . . H16A H 0.2116 0.6382 0.5354 0.052 Uiso 1 1 calc R . . C17A C 0.2622(2) 0.4915(7) 0.4057(7) 0.0402(16) Uani 1 1 d . . . C18A C 0.3116(2) 0.4889(6) 0.3130(8) 0.0389(14) Uani 1 1 d . . . H18A H 0.3236 0.3931 0.2686 0.047 Uiso 1 1 calc R . . C19A C 0.3436(2) 0.6252(7) 0.2846(6) 0.0352(15) Uani 1 1 d . . . H19A H 0.3777 0.6214 0.2221 0.042 Uiso 1 1 calc R . . C20A C 0.2273(3) 0.3416(9) 0.4382(8) 0.066(2) Uani 1 1 d . . . H20A H 0.1849 0.3671 0.4525 0.098 Uiso 1 1 calc R . . H20B H 0.2431 0.2927 0.5280 0.098 Uiso 1 1 calc R . . H20C H 0.2315 0.2690 0.3551 0.098 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 C1A 0.030(3) 0.033(4) 0.023(4) -0.007(3) 0.000(3) -0.004(3) S2A 0.0413(7) 0.0330(8) 0.0210(6) 0.0006(10) -0.0038(8) -0.0047(8) O1A 0.0495(19) 0.038(2) 0.040(2) 0.002(3) -0.011(3) 0.006(2) O2A 0.052(2) 0.050(3) 0.020(2) 0.001(2) 0.0048(19) -0.016(2) N3A 0.032(3) 0.033(3) 0.020(3) -0.008(3) -0.001(2) 0.001(2) C4A 0.035(3) 0.039(4) 0.031(3) -0.002(3) 0.003(3) 0.000(3) C5A 0.038(3) 0.035(4) 0.018(3) -0.005(3) 0.001(3) 0.002(3) C6A 0.037(3) 0.037(4) 0.028(4) 0.003(3) 0.000(3) -0.009(3) N7A 0.045(3) 0.029(3) 0.018(2) 0.001(3) 0.001(2) -0.010(3) C8A 0.052(4) 0.031(4) 0.017(3) -0.005(3) -0.003(3) 0.001(3) C9A 0.057(4) 0.024(4) 0.018(3) -0.005(3) 0.000(3) 0.004(3) C10A 0.055(3) 0.039(4) 0.021(3) -0.002(4) 0.007(3) 0.002(3) C11A 0.081(5) 0.038(4) 0.029(3) -0.001(4) -0.005(4) 0.002(4) C12A 0.053(3) 0.037(4) 0.045(4) -0.022(5) -0.020(5) 0.015(3) C13A 0.049(3) 0.027(4) 0.050(4) -0.009(4) 0.001(3) 0.002(3) C14A 0.042(3) 0.041(4) 0.023(3) 0.006(4) -0.002(3) 0.004(4) C15A 0.039(3) 0.042(4) 0.037(4) -0.007(4) 0.004(3) 0.005(3) C16A 0.038(3) 0.046(4) 0.045(4) 0.005(4) 0.012(3) -0.009(4) C17A 0.041(3) 0.038(4) 0.041(4) -0.003(4) 0.004(3) -0.011(3) C18A 0.045(3) 0.032(3) 0.039(3) -0.015(5) 0.010(4) -0.008(3) C19A 0.037(3) 0.042(4) 0.027(4) -0.002(3) 0.004(3) -0.002(3) C20A 0.055(4) 0.062(5) 0.080(5) -0.018(5) 0.022(4) -0.017(4) _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 C1A C19A 1.374(7) . ? C1A C15A 1.389(7) . ? C1A S2A 1.765(5) . ? S2A O1A 1.431(3) . ? S2A O2A 1.443(4) . ? S2A N3A 1.612(5) . ? N3A C4A 1.479(7) . ? N3A H3A 0.98(2) . ? C4A C5A 1.509(7) . ? C4A H4AA 0.9800 . ? C4A H4BA 0.9800 . ? C5A C6A 1.522(7) . ? C5A H5AA 0.9800 . ? C5A H5BA 0.9800 . ? C6A N7A 1.462(6) . ? C6A H6AA 0.9800 . ? C6A H6BA 0.9800 . ? N7A C8A 1.481(6) . ? N7A H7A 0.98(2) . ? C8A C9A 1.503(7) . ? C8A H8AA 0.9800 . ? C8A H8BA 0.9800 . ? C9A C14A 1.368(8) . ? C9A C10A 1.401(8) . ? C10A C11A 1.374(8) . ? C10A H10A 0.9400 . ? C11A C12A 1.370(8) . ? C11A H11A 0.9400 . ? C12A C13A 1.385(9) . ? C12A H12A 0.9400 . ? C13A C14A 1.390(7) . ? C13A H13A 0.9400 . ? C14A H14A 0.9400 . ? C15A C16A 1.380(8) . ? C15A H15A 0.9400 . ? C16A C17A 1.398(8) . ? C16A H16A 0.9400 . ? C17A C18A 1.373(8) . ? C17A C20A 1.511(8) . ? C18A C19A 1.375(7) . ? C18A H18A 0.9400 . ? C19A H19A 0.9400 . ? C20A H20A 0.9700 . ? C20A H20B 0.9700 . ? C20A H20C 0.9700 . ? 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 C19A C1A C15A 119.9(5) . . ? C19A C1A S2A 120.7(4) . . ? C15A C1A S2A 119.4(5) . . ? O1A S2A O2A 119.7(3) . . ? O1A S2A N3A 108.2(3) . . ? O2A S2A N3A 105.4(2) . . ? O1A S2A C1A 107.3(2) . . ? O2A S2A C1A 106.5(3) . . ? N3A S2A C1A 109.5(3) . . ? C4A N3A S2A 119.6(3) . . ? C4A N3A H3A 116(3) . . ? S2A N3A H3A 116(3) . . ? N3A C4A C5A 109.5(4) . . ? N3A C4A H4AA 109.8 . . ? C5A C4A H4AA 109.8 . . ? N3A C4A H4BA 109.8 . . ? C5A C4A H4BA 109.8 . . ? H4AA C4A H4BA 108.2 . . ? C4A C5A C6A 112.2(4) . . ? C4A C5A H5AA 109.2 . . ? C6A C5A H5AA 109.2 . . ? C4A C5A H5BA 109.2 . . ? C6A C5A H5BA 109.2 . . ? H5AA C5A H5BA 107.9 . . ? N7A C6A C5A 110.7(4) . . ? N7A C6A H6AA 109.5 . . ? C5A C6A H6AA 109.5 . . ? N7A C6A H6BA 109.5 . . ? C5A C6A H6BA 109.5 . . ? H6AA C6A H6BA 108.1 . . ? C6A N7A C8A 111.7(4) . . ? C6A N7A H7A 108(3) . . ? C8A N7A H7A 107(3) . . ? N7A C8A C9A 111.2(4) . . ? N7A C8A H8AA 109.4 . . ? C9A C8A H8AA 109.4 . . ? N7A C8A H8BA 109.4 . . ? C9A C8A H8BA 109.4 . . ? H8AA C8A H8BA 108.0 . . ? C14A C9A C10A 118.4(5) . . ? C14A C9A C8A 123.5(5) . . ? C10A C9A C8A 118.0(5) . . ? C11A C10A C9A 120.6(6) . . ? C11A C10A H10A 119.7 . . ? C9A C10A H10A 119.7 . . ? C12A C11A C10A 120.3(6) . . ? C12A C11A H11A 119.8 . . ? C10A C11A H11A 119.8 . . ? C11A C12A C13A 120.1(6) . . ? C11A C12A H12A 119.9 . . ? C13A C12A H12A 119.9 . . ? C12A C13A C14A 119.3(6) . . ? C12A C13A H13A 120.4 . . ? C14A C13A H13A 120.4 . . ? C9A C14A C13A 121.3(5) . . ? C9A C14A H14A 119.3 . . ? C13A C14A H14A 119.3 . . ? C16A C15A C1A 119.2(6) . . ? C16A C15A H15A 120.4 . . ? C1A C15A H15A 120.4 . . ? C15A C16A C17A 120.9(5) . . ? C15A C16A H16A 119.6 . . ? C17A C16A H16A 119.6 . . ? C18A C17A C16A 118.8(6) . . ? C18A C17A C20A 120.6(6) . . ? C16A C17A C20A 120.6(5) . . ? C17A C18A C19A 120.5(5) . . ? C17A C18A H18A 119.7 . . ? C19A C18A H18A 119.7 . . ? C1A C19A C18A 120.7(5) . . ? C1A C19A H19A 119.6 . . ? C18A C19A H19A 119.6 . . ? C17A C20A H20A 109.5 . . ? C17A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C17A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.257 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.057 data_9 _database_code_depnum_ccdc_archive 'CCDC 233478' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H24 N2 O2 S' _chemical_formula_sum 'C14 H24 N2 O2 S' _chemical_formula_weight 284.41 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/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 15.891(3) _cell_length_b 6.5484(12) _cell_length_c 15.549(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.131(15) _cell_angle_gamma 90.00 _cell_volume 1561.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 52 _cell_measurement_theta_min 12 _cell_measurement_theta_max 14 _exptl_crystal_description lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(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 'Stoe Stadi-4 4-circle diffractometer' _diffrn_measurement_method 'Omega-theta with learnt-profile (Clegg)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 5832 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 24.93 _reflns_number_total 2726 _reflns_number_gt 1654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _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. All hydrogen atoms bonded to carbon atoms were placed in calculated positions and refined using a riding model, and those bonded to nitrogen were located on the difference map and refined isotropically. ; _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^)+(0.0495P)^2^+0.7182P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2726 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1074 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _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 C11A C 0.1547(2) 1.3865(6) 0.5213(3) 0.0565(11) Uani 1 1 d . . . H11A H 0.1310 1.3111 0.4666 0.085 Uiso 1 1 calc R . . H11B H 0.1456 1.5316 0.5099 0.085 Uiso 1 1 calc R . . H11C H 0.1255 1.3444 0.5659 0.085 Uiso 1 1 calc R . . C10A C 0.2512(2) 1.3437(5) 0.5547(3) 0.0465(10) Uani 1 1 d . . . H10A H 0.2749 1.4226 0.6092 0.056 Uiso 1 1 calc R . . H10B H 0.2804 1.3901 0.5099 0.056 Uiso 1 1 calc R . . C9A C 0.2718(2) 1.1198(5) 0.5740(2) 0.0392(9) Uani 1 1 d . . . H9A H 0.2520 1.0794 0.6263 0.047 Uiso 1 1 calc R . . H9B H 0.2394 1.0383 0.5233 0.047 Uiso 1 1 calc R . . C8A C 0.3677(2) 1.0738(5) 0.5912(2) 0.0382(9) Uani 1 1 d . . . H8A H 0.3859 1.0993 0.5366 0.046 Uiso 1 1 calc R . . H8B H 0.4005 1.1670 0.6372 0.046 Uiso 1 1 calc R . . N7A N 0.38971(18) 0.8636(4) 0.6200(2) 0.0327(7) Uani 1 1 d . . . H7A H 0.357(2) 0.790(5) 0.581(2) 0.041(11) Uiso 1 1 d . . . C6A C 0.4791(2) 0.8124(5) 0.6182(2) 0.0364(9) Uani 1 1 d . . . H6A H 0.5197 0.9080 0.6563 0.044 Uiso 1 1 calc R . . H6B H 0.4848 0.8272 0.5573 0.044 Uiso 1 1 calc R . . C5A C 0.5026(2) 0.5967(5) 0.6500(2) 0.0371(9) Uani 1 1 d . . . H5A H 0.4912 0.5776 0.7085 0.045 Uiso 1 1 calc R . . H5B H 0.4661 0.5002 0.6084 0.045 Uiso 1 1 calc R . . C4A C 0.5972(2) 0.5527(5) 0.6570(2) 0.0362(8) Uani 1 1 d . . . H4A H 0.6080 0.5642 0.5979 0.043 Uiso 1 1 calc R . . H4B H 0.6337 0.6536 0.6961 0.043 Uiso 1 1 calc R . . N3A N 0.62082(17) 0.3464(4) 0.6926(2) 0.0341(7) Uani 1 1 d . . . H3A H 0.622(2) 0.332(5) 0.745(2) 0.035(11) Uiso 1 1 d . . . S2A S 0.70149(5) 0.22956(13) 0.66981(6) 0.0357(3) Uani 1 1 d . . . O1A O 0.69537(15) 0.2615(4) 0.57750(15) 0.0484(7) Uani 1 1 d . . . O2A O 0.70215(15) 0.0258(4) 0.70369(17) 0.0512(7) Uani 1 1 d . . . C1A C 0.79913(19) 0.3488(5) 0.7305(2) 0.0304(8) Uani 1 1 d . . . C12A C 0.8529(2) 0.2468(6) 0.8012(2) 0.0412(9) Uani 1 1 d . . . H12A H 0.8384 0.1152 0.8168 0.049 Uiso 1 1 calc R . . C13A C 0.9289(2) 0.3406(6) 0.8493(2) 0.0470(10) Uani 1 1 d . . . H13A H 0.9659 0.2710 0.8973 0.056 Uiso 1 1 calc R . . C14A C 0.9512(2) 0.5350(6) 0.8279(2) 0.0446(10) Uani 1 1 d . . . C15A C 0.8957(2) 0.6336(6) 0.7569(2) 0.0449(10) Uani 1 1 d . . . H15A H 0.9097 0.7658 0.7417 0.054 Uiso 1 1 calc R . . C16A C 0.8199(2) 0.5429(5) 0.7079(2) 0.0385(9) Uani 1 1 d . . . H16A H 0.7830 0.6122 0.6596 0.046 Uiso 1 1 calc R . . C17A C 1.0337(2) 0.6367(7) 0.8812(3) 0.0661(13) Uani 1 1 d . . . H17A H 1.0385 0.6206 0.9442 0.099 Uiso 1 1 calc R . . H17B H 1.0320 0.7810 0.8665 0.099 Uiso 1 1 calc R . . H17C H 1.0837 0.5740 0.8669 0.099 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 C11A 0.055(2) 0.059(3) 0.052(3) 0.003(2) 0.0072(19) 0.022(2) C10A 0.050(2) 0.042(2) 0.046(2) 0.0068(18) 0.0091(18) 0.0059(18) C9A 0.0373(19) 0.042(2) 0.038(2) -0.0005(18) 0.0105(16) 0.0006(17) C8A 0.0380(19) 0.033(2) 0.043(2) 0.0017(17) 0.0096(16) -0.0009(16) N7A 0.0300(15) 0.0308(16) 0.0353(17) -0.0003(15) 0.0047(13) -0.0016(13) C6A 0.0316(18) 0.037(2) 0.042(2) 0.0041(16) 0.0115(15) 0.0005(15) C5A 0.0318(18) 0.034(2) 0.043(2) 0.0055(17) 0.0059(16) -0.0030(15) C4A 0.0328(18) 0.033(2) 0.042(2) 0.0058(17) 0.0073(15) 0.0029(16) N3A 0.0326(16) 0.0342(17) 0.0343(19) 0.0055(14) 0.0068(14) -0.0012(12) S2A 0.0352(5) 0.0306(5) 0.0384(5) -0.0059(4) 0.0045(3) -0.0006(4) O1A 0.0546(15) 0.0561(17) 0.0315(14) -0.0124(14) 0.0060(11) 0.0021(14) O2A 0.0474(15) 0.0276(14) 0.0714(19) 0.0009(13) 0.0030(13) 0.0004(12) C1A 0.0288(17) 0.0333(19) 0.0313(19) -0.0038(15) 0.0114(15) -0.0003(15) C12A 0.0381(19) 0.041(2) 0.044(2) 0.0083(19) 0.0111(16) 0.0011(18) C13A 0.037(2) 0.063(3) 0.038(2) 0.0056(19) 0.0048(16) -0.0021(18) C14A 0.0359(19) 0.061(3) 0.037(2) -0.012(2) 0.0101(17) -0.0102(19) C15A 0.046(2) 0.041(2) 0.049(2) -0.0012(19) 0.0142(19) -0.0117(19) C16A 0.039(2) 0.041(2) 0.036(2) 0.0020(17) 0.0108(16) -0.0002(17) C17A 0.050(2) 0.089(3) 0.057(3) -0.010(3) 0.010(2) -0.028(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11A C10A 1.512(5) . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C11A H11C 0.9700 . ? C10A C9A 1.515(5) . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C9A C8A 1.508(4) . ? C9A H9A 0.9800 . ? C9A H9B 0.9800 . ? C8A N7A 1.461(4) . ? C8A H8A 0.9800 . ? C8A H8B 0.9800 . ? N7A C6A 1.466(4) . ? N7A H7A 0.85(3) . ? C6A C5A 1.511(4) . ? C6A H6A 0.9800 . ? C6A H6B 0.9800 . ? C5A C4A 1.506(4) . ? C5A H5A 0.9800 . ? C5A H5B 0.9800 . ? C4A N3A 1.471(4) . ? C4A H4A 0.9800 . ? C4A H4B 0.9800 . ? N3A S2A 1.610(3) . ? N3A H3A 0.82(3) . ? S2A O1A 1.428(2) . ? S2A O2A 1.433(2) . ? S2A C1A 1.773(3) . ? C1A C12A 1.377(4) . ? C1A C16A 1.382(5) . ? C12A C13A 1.386(5) . ? C12A H12A 0.9400 . ? C13A C14A 1.385(5) . ? C13A H13A 0.9400 . ? C14A C15A 1.380(5) . ? C14A C17A 1.510(5) . ? C15A C16A 1.380(5) . ? C15A H15A 0.9400 . ? C16A H16A 0.9400 . ? C17A H17A 0.9700 . ? C17A H17B 0.9700 . ? C17A H17C 0.9700 . ? 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 C10A C11A H11A 109.5 . . ? C10A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C10A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C11A C10A C9A 113.2(3) . . ? C11A C10A H10A 108.9 . . ? C9A C10A H10A 108.9 . . ? C11A C10A H10B 108.9 . . ? C9A C10A H10B 108.9 . . ? H10A C10A H10B 107.7 . . ? C8A C9A C10A 112.6(3) . . ? C8A C9A H9A 109.1 . . ? C10A C9A H9A 109.1 . . ? C8A C9A H9B 109.1 . . ? C10A C9A H9B 109.1 . . ? H9A C9A H9B 107.8 . . ? N7A C8A C9A 113.1(3) . . ? N7A C8A H8A 109.0 . . ? C9A C8A H8A 109.0 . . ? N7A C8A H8B 109.0 . . ? C9A C8A H8B 109.0 . . ? H8A C8A H8B 107.8 . . ? C8A N7A C6A 111.4(3) . . ? C8A N7A H7A 105(2) . . ? C6A N7A H7A 106(2) . . ? N7A C6A C5A 111.5(3) . . ? N7A C6A H6A 109.3 . . ? C5A C6A H6A 109.3 . . ? N7A C6A H6B 109.3 . . ? C5A C6A H6B 109.3 . . ? H6A C6A H6B 108.0 . . ? C4A C5A C6A 111.1(3) . . ? C4A C5A H5A 109.4 . . ? C6A C5A H5A 109.4 . . ? C4A C5A H5B 109.4 . . ? C6A C5A H5B 109.4 . . ? H5A C5A H5B 108.0 . . ? N3A C4A C5A 110.8(3) . . ? N3A C4A H4A 109.5 . . ? C5A C4A H4A 109.5 . . ? N3A C4A H4B 109.5 . . ? C5A C4A H4B 109.5 . . ? H4A C4A H4B 108.1 . . ? C4A N3A S2A 119.5(2) . . ? C4A N3A H3A 115(2) . . ? S2A N3A H3A 111(2) . . ? O1A S2A O2A 119.84(16) . . ? O1A S2A N3A 107.62(15) . . ? O2A S2A N3A 106.93(16) . . ? O1A S2A C1A 106.94(15) . . ? O2A S2A C1A 107.01(15) . . ? N3A S2A C1A 108.05(15) . . ? C12A C1A C16A 120.6(3) . . ? C12A C1A S2A 119.1(3) . . ? C16A C1A S2A 120.2(3) . . ? C1A C12A C13A 119.2(3) . . ? C1A C12A H12A 120.4 . . ? C13A C12A H12A 120.4 . . ? C14A C13A C12A 121.3(4) . . ? C14A C13A H13A 119.3 . . ? C12A C13A H13A 119.3 . . ? C15A C14A C13A 118.1(3) . . ? C15A C14A C17A 121.0(4) . . ? C13A C14A C17A 120.9(4) . . ? C16A C15A C14A 121.6(4) . . ? C16A C15A H15A 119.2 . . ? C14A C15A H15A 119.2 . . ? C15A C16A C1A 119.2(3) . . ? C15A C16A H16A 120.4 . . ? C1A C16A H16A 120.4 . . ? C14A C17A H17A 109.5 . . ? C14A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C14A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.93 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.255 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.053 data_10 _database_code_depnum_ccdc_archive 'CCDC 233479' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N2 O2 S' _chemical_formula_sum 'C13 H14 N2 O2 S' _chemical_formula_weight 262.32 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.245(8) _cell_length_b 6.100(5) _cell_length_c 18.916(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.50(8) _cell_angle_gamma 90.00 _cell_volume 1283.4(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 15 _cell_measurement_theta_max 16 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe Stadi-4 4-circle diffractometer' _diffrn_measurement_method Omega-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3869 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2503 _reflns_number_gt 2343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _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. All hydrogen atoms bonded to carbon atoms were placed in calculated positions and refined using a riding model, and those bonded to nitrogen were located on the difference map and refined isotropically. ; _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^)+(0.0509P)^2^+0.1534P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0093(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(7) _refine_ls_number_reflns 2503 _refine_ls_number_parameters 352 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _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 C1A C 0.7742(2) 0.3882(5) 0.52992(13) 0.0252(6) Uani 1 1 d . . . S2A S 0.64437(6) 0.52780(11) 0.49078(3) 0.02476(18) Uani 1 1 d . . . O1A O 0.68182(18) 0.7321(4) 0.46387(10) 0.0350(5) Uani 1 1 d . . . O2A O 0.56500(17) 0.5274(4) 0.54406(9) 0.0357(5) Uani 1 1 d . . . N3A N 0.5734(2) 0.3907(5) 0.42497(12) 0.0263(5) Uani 1 1 d . . . H3A H 0.534(2) 0.299(6) 0.4352(15) 0.024(8) Uiso 1 1 d . . . C4A C 0.6170(2) 0.3686(5) 0.35753(13) 0.0236(6) Uani 1 1 d . . . C5A C 0.5862(2) 0.5312(5) 0.30607(13) 0.0276(6) Uani 1 1 d . . . N6A N 0.5137(2) 0.7034(5) 0.31779(16) 0.0374(6) Uani 1 1 d . . . H6AA H 0.515(3) 0.805(8) 0.289(2) 0.062(13) Uiso 1 1 d . . . H6BA H 0.511(3) 0.740(7) 0.3619(19) 0.042(10) Uiso 1 1 d . . . C7A C 0.7624(3) 0.1828(5) 0.55914(15) 0.0330(7) Uani 1 1 d . . . H7A H 0.6870 0.1097 0.5527 0.040 Uiso 1 1 calc R . . C8A C 0.8628(3) 0.0861(6) 0.59787(15) 0.0399(7) Uani 1 1 d . . . H8A H 0.8559 -0.0561 0.6173 0.048 Uiso 1 1 calc R . . C9A C 0.9737(3) 0.1919(7) 0.60908(16) 0.0401(8) Uani 1 1 d . . . C10A C 0.9833(3) 0.3944(7) 0.57802(17) 0.0426(8) Uani 1 1 d . . . H10A H 1.0587 0.4674 0.5841 0.051 Uiso 1 1 calc R . . C11A C 0.8838(2) 0.4935(6) 0.53791(15) 0.0320(7) Uani 1 1 d . . . H11A H 0.8915 0.6323 0.5163 0.038 Uiso 1 1 calc R . . C12A C 1.0806(3) 0.0889(10) 0.6550(2) 0.0719(14) Uani 1 1 d . . . H12A H 1.1550 0.1459 0.6407 0.108 Uiso 1 1 calc R . . H12B H 1.0777 -0.0706 0.6487 0.108 Uiso 1 1 calc R . . H12C H 1.0785 0.1246 0.7053 0.108 Uiso 1 1 calc R . . C13A C 0.6258(3) 0.5026(6) 0.23959(14) 0.0354(7) Uani 1 1 d . . . H13A H 0.6085 0.6116 0.2037 0.042 Uiso 1 1 calc R . . C14A C 0.6887(3) 0.3197(7) 0.22608(15) 0.0415(8) Uani 1 1 d . . . H14A H 0.7148 0.3043 0.1808 0.050 Uiso 1 1 calc R . . C15A C 0.7154(3) 0.1567(6) 0.27644(16) 0.0401(8) Uani 1 1 d . . . H15A H 0.7571 0.0283 0.2657 0.048 Uiso 1 1 calc R . . C16A C 0.6800(2) 0.1844(5) 0.34331(15) 0.0303(6) Uani 1 1 d . . . H16A H 0.6993 0.0759 0.3792 0.036 Uiso 1 1 calc R . . C1B C 0.3542(2) 0.7593(5) 0.12170(13) 0.0226(6) Uani 1 1 d . . . S2B S 0.39447(5) 0.59356(11) 0.05248(3) 0.02166(17) Uani 1 1 d . . . O1B O 0.52388(15) 0.6007(4) 0.05798(9) 0.0294(4) Uani 1 1 d . . . O2B O 0.33452(18) 0.3878(3) 0.05455(10) 0.0306(5) Uani 1 1 d . . . N3B N 0.3443(2) 0.7065(5) -0.02410(12) 0.0224(5) Uani 1 1 d . . . H3B H 0.377(3) 0.795(6) -0.0299(15) 0.019(9) Uiso 1 1 d . . . C4B C 0.2165(2) 0.7114(5) -0.04885(12) 0.0218(5) Uani 1 1 d . . . C5B C 0.1666(2) 0.5363(5) -0.09124(12) 0.0240(5) Uani 1 1 d . . . N6B N 0.2356(2) 0.3685(5) -0.11153(13) 0.0302(6) Uani 1 1 d . . . H6AB H 0.201(3) 0.246(7) -0.1280(17) 0.040(9) Uiso 1 1 d . . . H6BB H 0.304(3) 0.338(6) -0.0815(17) 0.038(9) Uiso 1 1 d . . . C7B C 0.2646(2) 0.6881(5) 0.15965(13) 0.0283(6) Uani 1 1 d . . . H7B H 0.2254 0.5517 0.1486 0.034 Uiso 1 1 calc R . . C8B C 0.2334(2) 0.8191(6) 0.21364(14) 0.0329(7) Uani 1 1 d . . . H8B H 0.1726 0.7708 0.2399 0.039 Uiso 1 1 calc R . . C9B C 0.2889(2) 1.0193(6) 0.23032(13) 0.0316(7) Uani 1 1 d . . . C10B C 0.3791(2) 1.0856(6) 0.19174(13) 0.0311(6) Uani 1 1 d . . . H10B H 0.4184 1.2219 0.2027 0.037 Uiso 1 1 calc R . . C11B C 0.4124(2) 0.9559(5) 0.13762(14) 0.0264(6) Uani 1 1 d . . . H11B H 0.4745 1.0021 0.1119 0.032 Uiso 1 1 calc R . . C12B C 0.2533(3) 1.1624(7) 0.28851(16) 0.0475(9) Uani 1 1 d . . . H12D H 0.1910 1.2657 0.2678 0.071 Uiso 1 1 calc R . . H12E H 0.3237 1.2440 0.3114 0.071 Uiso 1 1 calc R . . H12F H 0.2221 1.0708 0.3242 0.071 Uiso 1 1 calc R . . C13B C 0.0429(2) 0.5479(6) -0.11692(14) 0.0326(7) Uani 1 1 d . . . H13B H 0.0058 0.4327 -0.1460 0.039 Uiso 1 1 calc R . . C14B C -0.0258(3) 0.7237(6) -0.10076(15) 0.0355(7) Uani 1 1 d . . . H14B H -0.1093 0.7268 -0.1186 0.043 Uiso 1 1 calc R . . C15B C 0.0248(2) 0.8943(6) -0.05915(15) 0.0336(7) Uani 1 1 d . . . H15B H -0.0230 1.0149 -0.0485 0.040 Uiso 1 1 calc R . . C16B C 0.1478(2) 0.8875(5) -0.03270(14) 0.0270(6) Uani 1 1 d . . . H16B H 0.1840 1.0036 -0.0037 0.032 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 C1A 0.0293(13) 0.0255(16) 0.0215(12) -0.0030(12) 0.0056(10) 0.0028(12) S2A 0.0287(3) 0.0234(4) 0.0217(3) -0.0011(3) 0.0024(2) 0.0030(3) O1A 0.0454(12) 0.0235(11) 0.0336(11) 0.0010(9) -0.0023(9) -0.0016(10) O2A 0.0383(10) 0.0435(13) 0.0264(9) -0.0019(10) 0.0083(8) 0.0131(11) N3A 0.0260(12) 0.0303(15) 0.0232(11) 0.0025(11) 0.0055(9) -0.0064(12) C4A 0.0226(12) 0.0284(16) 0.0189(12) -0.0005(12) 0.0002(10) -0.0080(12) C5A 0.0225(12) 0.0320(16) 0.0260(13) -0.0003(13) -0.0038(10) -0.0068(13) N6A 0.0428(15) 0.0343(16) 0.0328(15) 0.0087(14) -0.0026(12) 0.0079(13) C7A 0.0330(15) 0.0296(16) 0.0368(16) 0.0046(14) 0.0063(13) 0.0009(14) C8A 0.0480(17) 0.0336(18) 0.0398(16) 0.0098(16) 0.0122(13) 0.0115(16) C9A 0.0314(16) 0.054(2) 0.0349(15) 0.0019(17) 0.0063(13) 0.0161(16) C10A 0.0274(15) 0.054(2) 0.0467(18) -0.0029(18) 0.0059(13) -0.0020(16) C11A 0.0307(15) 0.0332(17) 0.0327(14) 0.0027(14) 0.0070(11) -0.0013(13) C12A 0.051(2) 0.098(4) 0.065(2) 0.023(3) -0.0001(17) 0.035(3) C13A 0.0388(15) 0.0450(19) 0.0208(12) 0.0057(14) -0.0011(11) -0.0121(16) C14A 0.0436(17) 0.060(2) 0.0220(14) -0.0098(16) 0.0083(13) -0.0144(18) C15A 0.0416(17) 0.040(2) 0.0391(17) -0.0136(15) 0.0070(13) -0.0021(15) C16A 0.0341(15) 0.0269(15) 0.0296(14) -0.0023(13) 0.0041(12) -0.0032(13) C1B 0.0232(12) 0.0247(15) 0.0189(12) 0.0024(11) 0.0002(10) 0.0054(12) S2B 0.0234(3) 0.0203(3) 0.0205(3) 0.0009(3) 0.0010(2) 0.0021(3) O1B 0.0240(9) 0.0343(11) 0.0286(9) -0.0040(10) -0.0002(7) 0.0073(9) O2B 0.0415(11) 0.0205(11) 0.0289(10) 0.0023(9) 0.0022(8) -0.0013(9) N3B 0.0227(11) 0.0222(13) 0.0218(11) 0.0042(11) 0.0017(9) -0.0041(11) C4B 0.0234(12) 0.0242(14) 0.0180(11) 0.0051(11) 0.0036(10) -0.0021(12) C5B 0.0266(12) 0.0241(14) 0.0208(11) 0.0032(12) 0.0024(10) -0.0014(12) N6B 0.0310(13) 0.0265(15) 0.0315(13) -0.0056(12) -0.0009(11) 0.0000(12) C7B 0.0251(13) 0.0322(16) 0.0267(13) 0.0051(13) 0.0007(10) -0.0021(13) C8B 0.0262(14) 0.048(2) 0.0248(13) 0.0063(14) 0.0051(11) 0.0045(14) C9B 0.0353(15) 0.0388(17) 0.0195(12) 0.0038(13) 0.0003(11) 0.0142(15) C10B 0.0403(15) 0.0250(15) 0.0267(13) 0.0023(13) 0.0008(11) 0.0044(14) C11B 0.0307(14) 0.0241(15) 0.0251(13) 0.0035(12) 0.0063(11) 0.0012(12) C12B 0.061(2) 0.054(2) 0.0281(15) -0.0025(16) 0.0087(14) 0.0184(18) C13B 0.0311(14) 0.0338(18) 0.0306(13) -0.0020(14) -0.0025(11) -0.0053(14) C14B 0.0236(14) 0.043(2) 0.0370(15) 0.0035(15) -0.0048(11) 0.0036(14) C15B 0.0289(14) 0.0347(18) 0.0365(15) 0.0024(14) 0.0029(12) 0.0092(14) C16B 0.0325(14) 0.0256(15) 0.0222(12) 0.0015(12) 0.0017(10) 0.0002(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C11A 1.378(4) . ? C1A C7A 1.384(4) . ? C1A S2A 1.757(3) . ? S2A O1A 1.433(2) . ? S2A O2A 1.442(2) . ? S2A N3A 1.610(3) . ? N3A C4A 1.439(3) . ? N3A H3A 0.76(3) . ? C4A C16A 1.377(4) . ? C4A C5A 1.397(4) . ? C5A N6A 1.368(4) . ? C5A C13A 1.405(4) . ? N6A H6AA 0.82(5) . ? N6A H6BA 0.87(3) . ? C7A C8A 1.383(4) . ? C7A H7A 0.9500 . ? C8A C9A 1.393(5) . ? C8A H8A 0.9500 . ? C9A C10A 1.379(5) . ? C9A C12A 1.512(5) . ? C10A C11A 1.393(4) . ? C10A H10A 0.9500 . ? C11A H11A 0.9500 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C13A C14A 1.366(5) . ? C13A H13A 0.9500 . ? C14A C15A 1.379(5) . ? C14A H14A 0.9500 . ? C15A C16A 1.392(4) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C1B C11B 1.378(4) . ? C1B C7B 1.390(4) . ? C1B S2B 1.766(3) . ? S2B O2B 1.428(2) . ? S2B O1B 1.444(2) . ? S2B N3B 1.628(3) . ? N3B C4B 1.444(4) . ? N3B H3B 0.67(3) . ? C4B C16B 1.384(4) . ? C4B C5B 1.402(4) . ? C5B N6B 1.373(4) . ? C5B C13B 1.406(4) . ? N6B H6AB 0.88(4) . ? N6B H6BB 0.91(3) . ? C7B C8B 1.382(4) . ? C7B H7B 0.9500 . ? C8B C9B 1.387(5) . ? C8B H8B 0.9500 . ? C9B C10B 1.394(4) . ? C9B C12B 1.505(4) . ? C10B C11B 1.388(4) . ? C10B H10B 0.9500 . ? C11B H11B 0.9500 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13B C14B 1.382(5) . ? C13B H13B 0.9500 . ? C14B C15B 1.377(5) . ? C14B H14B 0.9500 . ? C15B C16B 1.399(4) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? 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 C11A C1A C7A 121.0(3) . . ? C11A C1A S2A 119.6(2) . . ? C7A C1A S2A 119.0(2) . . ? O1A S2A O2A 119.64(14) . . ? O1A S2A N3A 108.39(13) . . ? O2A S2A N3A 104.61(13) . . ? O1A S2A C1A 107.57(14) . . ? O2A S2A C1A 105.46(13) . . ? N3A S2A C1A 111.09(15) . . ? C4A N3A S2A 122.6(2) . . ? C4A N3A H3A 116(2) . . ? S2A N3A H3A 115(2) . . ? C16A C4A C5A 121.7(2) . . ? C16A C4A N3A 120.1(2) . . ? C5A C4A N3A 118.0(3) . . ? N6A C5A C4A 121.6(3) . . ? N6A C5A C13A 121.0(3) . . ? C4A C5A C13A 117.2(3) . . ? C5A N6A H6AA 114(3) . . ? C5A N6A H6BA 118(2) . . ? H6AA N6A H6BA 116(4) . . ? C8A C7A C1A 118.6(3) . . ? C8A C7A H7A 120.7 . . ? C1A C7A H7A 120.7 . . ? C7A C8A C9A 121.7(3) . . ? C7A C8A H8A 119.2 . . ? C9A C8A H8A 119.2 . . ? C10A C9A C8A 118.4(3) . . ? C10A C9A C12A 120.8(4) . . ? C8A C9A C12A 120.9(4) . . ? C9A C10A C11A 120.9(3) . . ? C9A C10A H10A 119.5 . . ? C11A C10A H10A 119.5 . . ? C1A C11A C10A 119.4(3) . . ? C1A C11A H11A 120.3 . . ? C10A C11A H11A 120.3 . . ? C9A C12A H12A 109.5 . . ? C9A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C9A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C14A C13A C5A 120.7(3) . . ? C14A C13A H13A 119.7 . . ? C5A C13A H13A 119.7 . . ? C13A C14A C15A 121.7(3) . . ? C13A C14A H14A 119.1 . . ? C15A C14A H14A 119.1 . . ? C14A C15A C16A 118.6(3) . . ? C14A C15A H15A 120.7 . . ? C16A C15A H15A 120.7 . . ? C4A C16A C15A 120.1(3) . . ? C4A C16A H16A 120.0 . . ? C15A C16A H16A 120.0 . . ? C11B C1B C7B 121.1(3) . . ? C11B C1B S2B 119.6(2) . . ? C7B C1B S2B 119.3(2) . . ? O2B S2B O1B 119.95(13) . . ? O2B S2B N3B 107.08(14) . . ? O1B S2B N3B 105.32(14) . . ? O2B S2B C1B 108.01(13) . . ? O1B S2B C1B 107.20(13) . . ? N3B S2B C1B 108.93(14) . . ? C4B N3B S2B 119.6(2) . . ? C4B N3B H3B 118(3) . . ? S2B N3B H3B 111(3) . . ? C16B C4B C5B 121.8(2) . . ? C16B C4B N3B 120.4(3) . . ? C5B C4B N3B 117.7(2) . . ? N6B C5B C4B 122.2(2) . . ? N6B C5B C13B 120.8(3) . . ? C4B C5B C13B 116.9(3) . . ? C5B N6B H6AB 119(2) . . ? C5B N6B H6BB 116(2) . . ? H6AB N6B H6BB 110(3) . . ? C8B C7B C1B 118.9(3) . . ? C8B C7B H7B 120.6 . . ? C1B C7B H7B 120.6 . . ? C7B C8B C9B 121.5(3) . . ? C7B C8B H8B 119.2 . . ? C9B C8B H8B 119.2 . . ? C8B C9B C10B 118.3(3) . . ? C8B C9B C12B 121.2(3) . . ? C10B C9B C12B 120.5(3) . . ? C11B C10B C9B 121.2(3) . . ? C11B C10B H10B 119.4 . . ? C9B C10B H10B 119.4 . . ? C1B C11B C10B 119.0(3) . . ? C1B C11B H11B 120.5 . . ? C10B C11B H11B 120.5 . . ? C9B C12B H12D 109.5 . . ? C9B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C9B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C14B C13B C5B 121.3(3) . . ? C14B C13B H13B 119.3 . . ? C5B C13B H13B 119.3 . . ? C15B C14B C13B 121.0(3) . . ? C15B C14B H14B 119.5 . . ? C13B C14B H14B 119.5 . . ? C14B C15B C16B 119.0(3) . . ? C14B C15B H15B 120.5 . . ? C16B C15B H15B 120.5 . . ? C4B C16B C15B 119.9(3) . . ? C4B C16B H16B 120.0 . . ? C15B C16B H16B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.195 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.040 data_12 _database_code_depnum_ccdc_archive 'CCDC 233480' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H30 N4 O5 S2 Zn' _chemical_formula_sum 'C19 H30 N4 O5 S2 Zn' _chemical_formula_weight 523.96 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/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 15.636(6) _cell_length_b 25.789(8) _cell_length_c 11.784(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.18(3) _cell_angle_gamma 90.00 _cell_volume 4752(3) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 82 _cell_measurement_theta_min 20 _cell_measurement_theta_max 22 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 1.246 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.306 _exptl_absorpt_correction_T_max 0.400 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(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 'Stoe Stadi-4 4-circle diffractometer' _diffrn_measurement_method Omega-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 5702 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 23.52 _reflns_number_total 5441 _reflns_number_gt 3760 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution sir92 _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _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 structure was determined to be twinned by a 2-fold axis parallel to the a axis and a twin law of 1 0 0 0 -1 0 0 0 -1 was applied within shelxtl. ; _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^)+(0.0764P)^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 5441 _refine_ls_number_parameters 568 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1467 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _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 Zn1 Zn 0.62790(8) -0.75227(5) 0.22839(10) 0.0424(4) Uani 1 1 d . . . C1A C 0.6354(6) -0.5943(4) 0.0853(9) 0.031(3) Uani 1 1 d . . . S2A S 0.62781(17) -0.66045(10) 0.0521(2) 0.0324(6) Uani 1 1 d . . . O1A O 0.5788(5) -0.6639(3) -0.0529(6) 0.051(2) Uani 1 1 d . . . O2A O 0.7150(4) -0.6792(3) 0.0440(6) 0.043(2) Uani 1 1 d . . . N3A N 0.5855(5) -0.6879(3) 0.1559(7) 0.029(2) Uani 1 1 d . . . C4A C 0.4928(6) -0.6834(4) 0.1663(9) 0.036(3) Uani 1 1 d . . . H4A1 H 0.4643 -0.7029 0.1055 0.043 Uiso 1 1 calc R . . H4A2 H 0.4753 -0.6470 0.1612 0.043 Uiso 1 1 calc R . . C5A C 0.4691(6) -0.7054(4) 0.2800(9) 0.042(3) Uani 1 1 d . . . H5A1 H 0.4893 -0.6821 0.3401 0.050 Uiso 1 1 calc R . . H5A2 H 0.4067 -0.7078 0.2856 0.050 Uiso 1 1 calc R . . N6A N 0.5065(5) -0.7565(3) 0.2958(7) 0.041(2) Uani 1 1 d . . . H6A1 H 0.4750 -0.7810 0.2591 0.049 Uiso 1 1 calc R . . H6A2 H 0.5090 -0.7647 0.3709 0.049 Uiso 1 1 calc R . . C7A C 0.6075(8) -0.5574(4) 0.0079(10) 0.050(3) Uani 1 1 d . . . H7A H 0.5796 -0.5677 -0.0593 0.060 Uiso 1 1 calc R . . C8A C 0.6207(9) -0.5056(5) 0.0300(10) 0.062(4) Uani 1 1 d . . . H8A H 0.6033 -0.4809 -0.0241 0.074 Uiso 1 1 calc R . . C9A C 0.6588(8) -0.4888(5) 0.1288(11) 0.049(3) Uani 1 1 d . . . C10A C 0.6852(8) -0.5259(5) 0.2033(11) 0.060(4) Uani 1 1 d . . . H10A H 0.7126 -0.5155 0.2706 0.072 Uiso 1 1 calc R . . C11A C 0.6733(7) -0.5773(5) 0.1841(10) 0.048(3) Uani 1 1 d . . . H11A H 0.6912 -0.6015 0.2389 0.058 Uiso 1 1 calc R . . C12A C 0.6741(11) -0.4313(4) 0.1514(14) 0.107(6) Uani 1 1 d . . . H12A H 0.6684 -0.4245 0.2320 0.160 Uiso 1 1 calc R . . H12B H 0.6324 -0.4109 0.1097 0.160 Uiso 1 1 calc R . . H12C H 0.7313 -0.4220 0.1269 0.160 Uiso 1 1 calc R . . C1B C 0.6327(7) -0.9038(4) 0.0834(8) 0.032(3) Uani 1 1 d . . . S2B S 0.66666(16) -0.84068(10) 0.0480(2) 0.0320(7) Uani 1 1 d . . . O1B O 0.7410(4) -0.8483(3) -0.0237(6) 0.0399(19) Uani 1 1 d . . . O2B O 0.5957(4) -0.8146(3) -0.0042(6) 0.0409(18) Uani 1 1 d . . . N3B N 0.6869(5) -0.8115(3) 0.1620(7) 0.031(2) Uani 1 1 d . . . C4B C 0.7611(6) -0.8285(4) 0.2311(9) 0.033(3) Uani 1 1 d . . . H4B1 H 0.8042 -0.8447 0.1826 0.040 Uiso 1 1 calc R . . H4B2 H 0.7428 -0.8538 0.2881 0.040 Uiso 1 1 calc R . . C5B C 0.7976(6) -0.7817(4) 0.2878(9) 0.038(3) Uani 1 1 d . . . H5B1 H 0.8386 -0.7923 0.3463 0.046 Uiso 1 1 calc R . . H5B2 H 0.8278 -0.7604 0.2320 0.046 Uiso 1 1 calc R . . N6B N 0.7277(4) -0.7510(3) 0.3402(6) 0.030(2) Uani 1 1 d . . . H6B1 H 0.7451 -0.7178 0.3528 0.036 Uiso 1 1 calc R . . H6B2 H 0.7120 -0.7652 0.4076 0.036 Uiso 1 1 calc R . . C7B C 0.6597(6) -0.9464(5) 0.0215(10) 0.044(3) Uani 1 1 d . . . H7B H 0.6982 -0.9417 -0.0388 0.052 Uiso 1 1 calc R . . C8B C 0.6311(8) -0.9952(5) 0.0467(10) 0.053(3) Uani 1 1 d . . . H8B H 0.6494 -1.0233 0.0022 0.064 Uiso 1 1 calc R . . C9B C 0.5761(7) -1.0041(5) 0.1359(10) 0.045(3) Uani 1 1 d . . . C10B C 0.5518(7) -0.9618(5) 0.1996(10) 0.047(3) Uani 1 1 d . . . H10B H 0.5153 -0.9669 0.2619 0.057 Uiso 1 1 calc R . . C11B C 0.5787(7) -0.9129(5) 0.1752(10) 0.051(3) Uani 1 1 d . . . H11B H 0.5608 -0.8850 0.2205 0.061 Uiso 1 1 calc R . . C12B C 0.5457(8) -1.0590(4) 0.1638(12) 0.062(4) Uani 1 1 d . . . H12D H 0.5069 -1.0709 0.1049 0.092 Uiso 1 1 calc R . . H12E H 0.5163 -1.0588 0.2361 0.092 Uiso 1 1 calc R . . H12F H 0.5946 -1.0820 0.1680 0.092 Uiso 1 1 calc R . . Zn2 Zn 0.87229(8) -0.25602(5) -0.06257(10) 0.0438(4) Uani 1 1 d . . . C1C C 0.8903(6) -0.0920(4) -0.1741(9) 0.035(3) Uani 1 1 d . . . S2C S 0.88423(17) -0.15678(10) -0.2232(2) 0.0327(7) Uani 1 1 d . . . O1C O 0.9340(5) -0.1572(3) -0.3279(6) 0.053(2) Uani 1 1 d . . . O2C O 0.7946(4) -0.1694(3) -0.2363(7) 0.047(2) Uani 1 1 d . . . N3C N 0.9212(5) -0.1926(3) -0.1295(7) 0.030(2) Uani 1 1 d . . . C4C C 1.0129(6) -0.1896(4) -0.1066(9) 0.036(3) Uani 1 1 d . . . H4C1 H 1.0311 -0.1533 -0.1039 0.043 Uiso 1 1 calc R . . H4C2 H 1.0446 -0.2070 -0.1674 0.043 Uiso 1 1 calc R . . C5C C 1.0316(6) -0.2150(4) 0.0032(10) 0.042(3) Uani 1 1 d . . . H5C1 H 1.0936 -0.2179 0.0141 0.051 Uiso 1 1 calc R . . H5C2 H 1.0082 -0.1943 0.0654 0.051 Uiso 1 1 calc R . . N6C N 0.9925(5) -0.2671(3) 0.0033(7) 0.038(2) Uani 1 1 d . . . H6C1 H 0.9897 -0.2800 0.0750 0.046 Uiso 1 1 calc R . . H6C2 H 1.0231 -0.2894 -0.0406 0.046 Uiso 1 1 calc R . . C7C C 0.9369(7) -0.0553(5) -0.2328(10) 0.046(3) Uani 1 1 d . . . H7C H 0.9641 -0.0643 -0.3011 0.055 Uiso 1 1 calc R . . C8C C 0.9434(7) -0.0053(5) -0.1905(10) 0.055(3) Uani 1 1 d . . . H8C H 0.9736 0.0198 -0.2320 0.066 Uiso 1 1 calc R . . C9C C 0.9065(7) 0.0081(5) -0.0889(10) 0.045(3) Uani 1 1 d . . . C10C C 0.8606(7) -0.0296(5) -0.0312(10) 0.051(3) Uani 1 1 d . . . H10C H 0.8335 -0.0209 0.0372 0.061 Uiso 1 1 calc R . . C11C C 0.8541(6) -0.0788(4) -0.0714(10) 0.039(3) Uani 1 1 d . . . H11C H 0.8247 -0.1041 -0.0291 0.047 Uiso 1 1 calc R . . C12C C 0.9144(8) 0.0633(4) -0.0409(12) 0.071(4) Uani 1 1 d . . . H12G H 0.9257 0.0616 0.0400 0.107 Uiso 1 1 calc R . . H12H H 0.8615 0.0820 -0.0541 0.107 Uiso 1 1 calc R . . H12I H 0.9611 0.0812 -0.0783 0.107 Uiso 1 1 calc R . . C1D C 0.8360(6) -0.4104(4) -0.1853(8) 0.028(3) Uani 1 1 d . . . S2D S 0.82198(16) -0.34582(11) -0.2373(2) 0.0341(7) Uani 1 1 d . . . O1D O 0.9016(4) -0.3281(3) -0.2834(6) 0.048(2) Uani 1 1 d . . . O2D O 0.7496(4) -0.3485(3) -0.3151(6) 0.045(2) Uani 1 1 d . . . N3D N 0.8039(5) -0.3112(3) -0.1307(7) 0.030(2) Uani 1 1 d . . . C4D C 0.7309(6) -0.3254(4) -0.0582(10) 0.044(3) Uani 1 1 d . . . H4D1 H 0.7476 -0.3534 -0.0065 0.053 Uiso 1 1 calc R . . H4D2 H 0.6834 -0.3378 -0.1054 0.053 Uiso 1 1 calc R . . C5D C 0.7033(6) -0.2793(4) 0.0083(9) 0.041(3) Uani 1 1 d . . . H5D1 H 0.6719 -0.2554 -0.0413 0.049 Uiso 1 1 calc R . . H5D2 H 0.6648 -0.2903 0.0692 0.049 Uiso 1 1 calc R . . N6D N 0.7776(4) -0.2529(3) 0.0570(7) 0.033(2) Uani 1 1 d . . . H6D1 H 0.7948 -0.2690 0.1219 0.040 Uiso 1 1 calc R . . H6D2 H 0.7646 -0.2194 0.0736 0.040 Uiso 1 1 calc R . . C7D C 0.8881(7) -0.4195(4) -0.0967(10) 0.041(3) Uani 1 1 d . . . H7D H 0.9196 -0.3925 -0.0632 0.050 Uiso 1 1 calc R . . C8D C 0.8943(7) -0.4695(5) -0.0561(10) 0.051(3) Uani 1 1 d . . . H8D H 0.9298 -0.4756 0.0070 0.061 Uiso 1 1 calc R . . C9D C 0.8514(6) -0.5110(5) -0.1030(10) 0.042(3) Uani 1 1 d . . . C10D C 0.7985(7) -0.5004(5) -0.1936(10) 0.046(3) Uani 1 1 d . . . H10D H 0.7674 -0.5273 -0.2280 0.056 Uiso 1 1 calc R . . C11D C 0.7906(6) -0.4503(5) -0.2343(9) 0.044(3) Uani 1 1 d . . . H11D H 0.7539 -0.4435 -0.2959 0.052 Uiso 1 1 calc R . . C12D C 0.8594(8) -0.5649(4) -0.0550(12) 0.064(4) Uani 1 1 d . . . H12J H 0.8028 -0.5799 -0.0464 0.096 Uiso 1 1 calc R . . H12K H 0.8874 -0.5634 0.0184 0.096 Uiso 1 1 calc R . . H12L H 0.8929 -0.5862 -0.1061 0.096 Uiso 1 1 calc R . . C1M C 1.6163(8) -0.1477(5) -0.0737(10) 0.072(4) Uani 1 1 d . . . H1M1 H 1.6659 -0.1524 -0.0251 0.108 Uiso 1 1 calc R . . H1M2 H 1.5652 -0.1585 -0.0335 0.108 Uiso 1 1 calc R . . H1M3 H 1.6113 -0.1114 -0.0943 0.108 Uiso 1 1 calc R . . O1M O 1.6258(7) -0.1782(4) -0.1738(8) 0.082(3) Uani 1 1 d . . . H1M H 1.5939 -0.2039 -0.1702 0.123 Uiso 1 1 calc R . . C2M C 1.1101(8) -0.3569(5) -0.2154(11) 0.066(4) Uani 1 1 d . . . H2M1 H 1.1510 -0.3459 -0.2722 0.100 Uiso 1 1 calc R . . H2M2 H 1.0526 -0.3537 -0.2457 0.100 Uiso 1 1 calc R . . H2M3 H 1.1210 -0.3928 -0.1952 0.100 Uiso 1 1 calc R . . O2M O 1.1183(5) -0.3259(4) -0.1195(8) 0.077(3) Uani 1 1 d . . . H2M H 1.1694 -0.3182 -0.1101 0.115 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 Zn1 0.0380(6) 0.0363(8) 0.0530(7) -0.0011(8) 0.0008(6) 0.0064(7) C1A 0.037(6) 0.020(7) 0.036(7) -0.003(6) 0.007(5) -0.004(5) S2A 0.0407(14) 0.0215(16) 0.0349(14) -0.0037(14) -0.0018(12) 0.0000(15) O1A 0.064(5) 0.036(5) 0.051(5) -0.011(4) -0.009(4) -0.008(4) O2A 0.035(4) 0.027(4) 0.065(5) -0.010(4) 0.019(4) 0.000(3) N3A 0.032(4) 0.014(5) 0.041(5) 0.000(4) 0.004(4) 0.002(4) C4A 0.033(6) 0.026(7) 0.048(7) 0.002(6) -0.001(5) -0.004(5) C5A 0.037(6) 0.044(8) 0.045(7) 0.003(6) -0.001(5) 0.017(6) N6A 0.024(4) 0.042(6) 0.056(6) 0.008(5) 0.002(4) 0.006(5) C7A 0.080(8) 0.023(8) 0.047(7) -0.004(7) -0.013(6) -0.003(7) C8A 0.102(10) 0.029(9) 0.054(8) 0.022(7) -0.006(8) 0.001(8) C9A 0.071(8) 0.024(8) 0.052(8) 0.005(7) 0.020(6) -0.011(6) C10A 0.085(9) 0.040(10) 0.054(9) -0.021(8) 0.013(7) -0.010(8) C11A 0.073(8) 0.037(9) 0.034(7) -0.009(6) -0.007(6) -0.007(7) C12A 0.195(18) 0.014(9) 0.112(14) -0.010(9) 0.043(13) -0.033(10) C1B 0.045(6) 0.023(7) 0.027(6) 0.006(5) -0.006(5) -0.008(6) S2B 0.0395(13) 0.0202(17) 0.0363(15) 0.0005(14) 0.0010(12) 0.0030(14) O1B 0.054(4) 0.029(4) 0.037(4) 0.004(4) 0.021(3) 0.003(4) O2B 0.049(4) 0.032(4) 0.042(4) 0.009(4) -0.009(4) 0.004(4) N3B 0.035(5) 0.024(5) 0.034(5) -0.004(4) -0.006(4) 0.010(4) C4B 0.035(5) 0.022(7) 0.043(6) 0.001(6) -0.002(5) 0.014(5) C5B 0.028(5) 0.029(7) 0.059(7) -0.014(6) -0.006(5) -0.003(5) N6B 0.034(4) 0.021(5) 0.033(4) -0.003(5) 0.010(3) 0.000(4) C7B 0.050(6) 0.028(8) 0.053(8) -0.004(7) 0.008(5) -0.015(6) C8B 0.073(8) 0.029(8) 0.057(8) -0.024(7) -0.003(7) -0.005(7) C9B 0.041(7) 0.039(9) 0.054(8) 0.005(7) 0.000(6) -0.006(6) C10B 0.065(8) 0.028(8) 0.049(8) 0.006(7) 0.016(6) -0.022(7) C11B 0.057(7) 0.054(10) 0.043(7) -0.007(7) 0.010(6) 0.009(7) C12B 0.066(8) 0.028(8) 0.091(10) 0.004(8) -0.009(7) -0.008(7) Zn2 0.0394(7) 0.0410(9) 0.0510(7) 0.0049(8) -0.0016(7) -0.0049(7) C1C 0.043(6) 0.030(7) 0.033(6) 0.003(6) -0.004(5) 0.001(6) S2C 0.0387(15) 0.0218(16) 0.0377(14) -0.0037(14) -0.0003(12) 0.0004(14) O1C 0.084(5) 0.042(5) 0.031(4) -0.006(4) 0.022(4) 0.003(5) O2C 0.050(5) 0.028(5) 0.063(5) 0.000(4) -0.011(4) 0.007(4) N3C 0.029(4) 0.011(5) 0.051(6) 0.004(4) 0.002(4) 0.002(4) C4C 0.031(6) 0.020(7) 0.058(7) 0.004(6) -0.001(5) 0.001(5) C5C 0.025(5) 0.047(8) 0.054(7) -0.008(7) -0.004(5) 0.004(5) N6C 0.041(5) 0.037(6) 0.037(5) 0.016(5) 0.002(4) 0.002(4) C7C 0.065(7) 0.027(8) 0.046(7) 0.008(7) 0.011(6) 0.007(6) C8C 0.069(8) 0.037(9) 0.057(9) 0.018(7) 0.008(6) 0.000(7) C9C 0.051(7) 0.022(8) 0.060(8) 0.001(7) -0.018(6) 0.010(6) C10C 0.063(8) 0.035(8) 0.055(8) -0.015(7) 0.017(6) 0.000(6) C11C 0.049(7) 0.024(8) 0.044(7) -0.005(6) 0.004(5) -0.006(5) C12C 0.087(9) 0.035(9) 0.090(11) 0.003(8) -0.031(8) 0.013(7) C1D 0.033(5) 0.025(7) 0.027(6) 0.003(5) -0.005(5) 0.001(5) S2D 0.0388(15) 0.0275(18) 0.0359(16) 0.0003(14) -0.0012(12) -0.0031(13) O1D 0.037(4) 0.055(5) 0.051(5) 0.000(4) 0.017(3) -0.009(4) O2D 0.053(4) 0.038(5) 0.045(5) 0.010(4) -0.018(4) -0.006(4) N3D 0.029(5) 0.019(5) 0.042(5) -0.008(4) 0.010(4) -0.007(4) C4D 0.038(6) 0.035(7) 0.059(8) -0.006(7) 0.005(5) -0.003(6) C5D 0.038(6) 0.044(8) 0.042(6) -0.005(6) 0.004(5) -0.003(6) N6D 0.038(4) 0.027(5) 0.035(5) 0.001(5) -0.005(4) 0.005(4) C7D 0.053(7) 0.011(7) 0.060(8) -0.009(6) -0.021(6) 0.007(6) C8D 0.055(7) 0.043(9) 0.056(7) -0.005(8) -0.013(6) 0.023(7) C9D 0.040(7) 0.034(9) 0.051(7) 0.000(7) 0.006(5) 0.004(6) C10D 0.047(7) 0.028(8) 0.064(8) -0.005(7) -0.010(6) -0.016(6) C11D 0.045(6) 0.051(9) 0.034(6) -0.004(7) -0.007(5) -0.006(6) C12D 0.080(9) 0.024(8) 0.088(10) 0.011(8) 0.005(7) 0.002(7) C1M 0.072(9) 0.081(11) 0.062(8) -0.003(8) -0.005(7) 0.008(8) O1M 0.084(6) 0.071(7) 0.090(7) 0.002(6) -0.001(6) -0.021(6) C2M 0.058(8) 0.068(10) 0.073(9) 0.002(8) -0.015(7) -0.014(7) O2M 0.059(5) 0.068(7) 0.102(7) -0.012(6) 0.001(6) 0.003(5) _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 Zn1 N3B 1.951(8) . ? Zn1 N3A 1.981(8) . ? Zn1 N6B 2.040(8) . ? Zn1 N6A 2.062(7) . ? C1A C11A 1.376(14) . ? C1A C7A 1.389(14) . ? C1A S2A 1.753(11) . ? S2A O2A 1.449(7) . ? S2A O1A 1.456(7) . ? S2A N3A 1.562(8) . ? N3A C4A 1.460(11) . ? C4A C5A 1.501(13) . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C5A N6A 1.454(12) . ? C5A H5A1 0.9800 . ? C5A H5A2 0.9800 . ? N6A H6A1 0.9100 . ? N6A H6A2 0.9100 . ? C7A C8A 1.376(15) . ? C7A H7A 0.9400 . ? C8A C9A 1.376(16) . ? C8A H8A 0.9400 . ? C9A C10A 1.361(17) . ? C9A C12A 1.525(17) . ? C10A C11A 1.358(15) . ? C10A H10A 0.9400 . ? C11A H11A 0.9400 . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C12A H12C 0.9700 . ? C1B C7B 1.385(14) . ? C1B C11B 1.393(15) . ? C1B S2B 1.763(10) . ? S2B O2B 1.434(7) . ? S2B O1B 1.453(6) . ? S2B N3B 1.570(8) . ? N3B C4B 1.481(11) . ? C4B C5B 1.492(13) . ? C4B H4B1 0.9800 . ? C4B H4B2 0.9800 . ? C5B N6B 1.485(11) . ? C5B H5B1 0.9800 . ? C5B H5B2 0.9800 . ? N6B H6B1 0.9100 . ? N6B H6B2 0.9100 . ? C7B C8B 1.368(15) . ? C7B H7B 0.9400 . ? C8B C9B 1.379(15) . ? C8B H8B 0.9400 . ? C9B C10B 1.379(16) . ? C9B C12B 1.529(16) . ? C10B C11B 1.361(15) . ? C10B H10B 0.9400 . ? C11B H11B 0.9400 . ? C12B H12D 0.9700 . ? C12B H12E 0.9700 . ? C12B H12F 0.9700 . ? Zn2 N3D 1.951(8) . ? Zn2 N3C 1.972(8) . ? Zn2 N6D 2.048(7) . ? Zn2 N6C 2.052(8) . ? C1C C11C 1.380(14) . ? C1C C7C 1.381(14) . ? C1C S2C 1.770(11) . ? S2C O2C 1.446(7) . ? S2C O1C 1.460(7) . ? S2C N3C 1.549(8) . ? N3C C4C 1.461(11) . ? C4C C5C 1.478(14) . ? C4C H4C1 0.9800 . ? C4C H4C2 0.9800 . ? C5C N6C 1.475(13) . ? C5C H5C1 0.9800 . ? C5C H5C2 0.9800 . ? N6C H6C1 0.9100 . ? N6C H6C2 0.9100 . ? C7C C8C 1.387(16) . ? C7C H7C 0.9400 . ? C8C C9C 1.376(16) . ? C8C H8C 0.9400 . ? C9C C10C 1.388(15) . ? C9C C12C 1.537(16) . ? C10C C11C 1.359(14) . ? C10C H10C 0.9400 . ? C11C H11C 0.9400 . ? C12C H12G 0.9700 . ? C12C H12H 0.9700 . ? C12C H12I 0.9700 . ? C1D C7D 1.344(14) . ? C1D C11D 1.377(14) . ? C1D S2D 1.787(11) . ? S2D O1D 1.435(7) . ? S2D O2D 1.456(7) . ? S2D N3D 1.568(8) . ? N3D C4D 1.475(12) . ? C4D C5D 1.488(13) . ? C4D H4D1 0.9800 . ? C4D H4D2 0.9800 . ? C5D N6D 1.464(12) . ? C5D H5D1 0.9800 . ? C5D H5D2 0.9800 . ? N6D H6D1 0.9100 . ? N6D H6D2 0.9100 . ? C7D C8D 1.378(15) . ? C7D H7D 0.9400 . ? C8D C9D 1.379(15) . ? C8D H8D 0.9400 . ? C9D C10D 1.376(15) . ? C9D C12D 1.506(16) . ? C10D C11D 1.382(15) . ? C10D H10D 0.9400 . ? C11D H11D 0.9400 . ? C12D H12J 0.9700 . ? C12D H12K 0.9700 . ? C12D H12L 0.9700 . ? C1M O1M 1.426(14) . ? C1M H1M1 0.9700 . ? C1M H1M2 0.9700 . ? C1M H1M3 0.9700 . ? O1M H1M 0.8300 . ? C2M O2M 1.389(13) . ? C2M H2M1 0.9700 . ? C2M H2M2 0.9700 . ? C2M H2M3 0.9700 . ? O2M H2M 0.8300 . ? 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 N3B Zn1 N3A 129.9(3) . . ? N3B Zn1 N6B 84.8(3) . . ? N3A Zn1 N6B 121.3(3) . . ? N3B Zn1 N6A 123.4(3) . . ? N3A Zn1 N6A 84.4(3) . . ? N6B Zn1 N6A 117.1(3) . . ? C11A C1A C7A 118.1(10) . . ? C11A C1A S2A 121.9(9) . . ? C7A C1A S2A 120.0(8) . . ? O2A S2A O1A 114.6(5) . . ? O2A S2A N3A 107.5(4) . . ? O1A S2A N3A 114.5(4) . . ? O2A S2A C1A 106.0(4) . . ? O1A S2A C1A 106.5(5) . . ? N3A S2A C1A 107.1(5) . . ? C4A N3A S2A 117.0(7) . . ? C4A N3A Zn1 111.1(6) . . ? S2A N3A Zn1 125.1(5) . . ? N3A C4A C5A 107.1(8) . . ? N3A C4A H4A1 110.3 . . ? C5A C4A H4A1 110.3 . . ? N3A C4A H4A2 110.3 . . ? C5A C4A H4A2 110.3 . . ? H4A1 C4A H4A2 108.6 . . ? N6A C5A C4A 110.8(9) . . ? N6A C5A H5A1 109.5 . . ? C4A C5A H5A1 109.5 . . ? N6A C5A H5A2 109.5 . . ? C4A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 108.1 . . ? C5A N6A Zn1 105.9(6) . . ? C5A N6A H6A1 110.6 . . ? Zn1 N6A H6A1 110.6 . . ? C5A N6A H6A2 110.6 . . ? Zn1 N6A H6A2 110.6 . . ? H6A1 N6A H6A2 108.7 . . ? C8A C7A C1A 119.6(11) . . ? C8A C7A H7A 120.2 . . ? C1A C7A H7A 120.2 . . ? C9A C8A C7A 122.0(11) . . ? C9A C8A H8A 119.0 . . ? C7A C8A H8A 119.0 . . ? C10A C9A C8A 117.0(11) . . ? C10A C9A C12A 121.5(13) . . ? C8A C9A C12A 121.4(13) . . ? C11A C10A C9A 122.5(12) . . ? C11A C10A H10A 118.7 . . ? C9A C10A H10A 118.7 . . ? C10A C11A C1A 120.7(12) . . ? C10A C11A H11A 119.7 . . ? C1A C11A H11A 119.7 . . ? C9A C12A H12A 109.5 . . ? C9A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C9A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C7B C1B C11B 117.6(10) . . ? C7B C1B S2B 121.0(8) . . ? C11B C1B S2B 121.4(9) . . ? O2B S2B O1B 115.7(4) . . ? O2B S2B N3B 107.2(4) . . ? O1B S2B N3B 113.7(4) . . ? O2B S2B C1B 107.5(4) . . ? O1B S2B C1B 104.8(5) . . ? N3B S2B C1B 107.5(5) . . ? C4B N3B S2B 119.0(6) . . ? C4B N3B Zn1 112.4(6) . . ? S2B N3B Zn1 128.6(5) . . ? N3B C4B C5B 107.8(8) . . ? N3B C4B H4B1 110.2 . . ? C5B C4B H4B1 110.2 . . ? N3B C4B H4B2 110.2 . . ? C5B C4B H4B2 110.2 . . ? H4B1 C4B H4B2 108.5 . . ? N6B C5B C4B 109.7(7) . . ? N6B C5B H5B1 109.7 . . ? C4B C5B H5B1 109.7 . . ? N6B C5B H5B2 109.7 . . ? C4B C5B H5B2 109.7 . . ? H5B1 C5B H5B2 108.2 . . ? C5B N6B Zn1 106.6(6) . . ? C5B N6B H6B1 110.4 . . ? Zn1 N6B H6B1 110.4 . . ? C5B N6B H6B2 110.4 . . ? Zn1 N6B H6B2 110.4 . . ? H6B1 N6B H6B2 108.6 . . ? C8B C7B C1B 120.9(10) . . ? C8B C7B H7B 119.5 . . ? C1B C7B H7B 119.5 . . ? C7B C8B C9B 121.6(11) . . ? C7B C8B H8B 119.2 . . ? C9B C8B H8B 119.2 . . ? C8B C9B C10B 117.2(11) . . ? C8B C9B C12B 120.9(12) . . ? C10B C9B C12B 121.9(11) . . ? C11B C10B C9B 122.1(11) . . ? C11B C10B H10B 118.9 . . ? C9B C10B H10B 118.9 . . ? C10B C11B C1B 120.5(11) . . ? C10B C11B H11B 119.7 . . ? C1B C11B H11B 119.7 . . ? C9B C12B H12D 109.5 . . ? C9B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C9B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? N3D Zn2 N3C 130.8(3) . . ? N3D Zn2 N6D 85.1(3) . . ? N3C Zn2 N6D 121.6(3) . . ? N3D Zn2 N6C 123.7(3) . . ? N3C Zn2 N6C 84.9(3) . . ? N6D Zn2 N6C 114.1(3) . . ? C11C C1C C7C 119.3(10) . . ? C11C C1C S2C 119.8(9) . . ? C7C C1C S2C 120.7(8) . . ? O2C S2C O1C 115.2(5) . . ? O2C S2C N3C 107.5(4) . . ? O1C S2C N3C 113.5(4) . . ? O2C S2C C1C 107.3(5) . . ? O1C S2C C1C 104.8(5) . . ? N3C S2C C1C 108.0(5) . . ? C4C N3C S2C 117.7(7) . . ? C4C N3C Zn2 110.5(6) . . ? S2C N3C Zn2 129.5(5) . . ? N3C C4C C5C 109.3(8) . . ? N3C C4C H4C1 109.8 . . ? C5C C4C H4C1 109.8 . . ? N3C C4C H4C2 109.8 . . ? C5C C4C H4C2 109.8 . . ? H4C1 C4C H4C2 108.3 . . ? N6C C5C C4C 108.9(9) . . ? N6C C5C H5C1 109.9 . . ? C4C C5C H5C1 109.9 . . ? N6C C5C H5C2 109.9 . . ? C4C C5C H5C2 109.9 . . ? H5C1 C5C H5C2 108.3 . . ? C5C N6C Zn2 104.6(6) . . ? C5C N6C H6C1 110.8 . . ? Zn2 N6C H6C1 110.8 . . ? C5C N6C H6C2 110.8 . . ? Zn2 N6C H6C2 110.8 . . ? H6C1 N6C H6C2 108.9 . . ? C1C C7C C8C 119.7(11) . . ? C1C C7C H7C 120.1 . . ? C8C C7C H7C 120.1 . . ? C9C C8C C7C 121.1(11) . . ? C9C C8C H8C 119.5 . . ? C7C C8C H8C 119.5 . . ? C8C C9C C10C 117.9(11) . . ? C8C C9C C12C 121.3(12) . . ? C10C C9C C12C 120.7(12) . . ? C11C C10C C9C 121.6(11) . . ? C11C C10C H10C 119.2 . . ? C9C C10C H10C 119.2 . . ? C10C C11C C1C 120.3(11) . . ? C10C C11C H11C 119.9 . . ? C1C C11C H11C 119.9 . . ? C9C C12C H12G 109.5 . . ? C9C C12C H12H 109.5 . . ? H12G C12C H12H 109.5 . . ? C9C C12C H12I 109.5 . . ? H12G C12C H12I 109.5 . . ? H12H C12C H12I 109.5 . . ? C7D C1D C11D 120.3(10) . . ? C7D C1D S2D 120.2(8) . . ? C11D C1D S2D 119.4(8) . . ? O1D S2D O2D 116.7(4) . . ? O1D S2D N3D 106.3(4) . . ? O2D S2D N3D 113.0(5) . . ? O1D S2D C1D 108.7(5) . . ? O2D S2D C1D 105.4(4) . . ? N3D S2D C1D 106.2(5) . . ? C4D N3D S2D 117.6(7) . . ? C4D N3D Zn2 111.6(6) . . ? S2D N3D Zn2 130.2(4) . . ? N3D C4D C5D 109.4(8) . . ? N3D C4D H4D1 109.8 . . ? C5D C4D H4D1 109.8 . . ? N3D C4D H4D2 109.8 . . ? C5D C4D H4D2 109.8 . . ? H4D1 C4D H4D2 108.2 . . ? N6D C5D C4D 110.3(8) . . ? N6D C5D H5D1 109.6 . . ? C4D C5D H5D1 109.6 . . ? N6D C5D H5D2 109.6 . . ? C4D C5D H5D2 109.6 . . ? H5D1 C5D H5D2 108.1 . . ? C5D N6D Zn2 106.6(6) . . ? C5D N6D H6D1 110.4 . . ? Zn2 N6D H6D1 110.4 . . ? C5D N6D H6D2 110.4 . . ? Zn2 N6D H6D2 110.4 . . ? H6D1 N6D H6D2 108.6 . . ? C1D C7D C8D 118.5(10) . . ? C1D C7D H7D 120.8 . . ? C8D C7D H7D 120.8 . . ? C7D C8D C9D 123.6(11) . . ? C7D C8D H8D 118.2 . . ? C9D C8D H8D 118.2 . . ? C10D C9D C8D 116.5(11) . . ? C10D C9D C12D 121.6(11) . . ? C8D C9D C12D 121.8(11) . . ? C9D C10D C11D 120.6(11) . . ? C9D C10D H10D 119.7 . . ? C11D C10D H10D 119.7 . . ? C1D C11D C10D 120.5(10) . . ? C1D C11D H11D 119.7 . . ? C10D C11D H11D 119.7 . . ? C9D C12D H12J 109.5 . . ? C9D C12D H12K 109.5 . . ? H12J C12D H12K 109.5 . . ? C9D C12D H12L 109.5 . . ? H12J C12D H12L 109.5 . . ? H12K C12D H12L 109.5 . . ? O1M C1M H1M1 109.5 . . ? O1M C1M H1M2 109.5 . . ? H1M1 C1M H1M2 109.5 . . ? O1M C1M H1M3 109.5 . . ? H1M1 C1M H1M3 109.5 . . ? H1M2 C1M H1M3 109.5 . . ? C1M O1M H1M 109.5 . . ? O2M C2M H2M1 109.5 . . ? O2M C2M H2M2 109.5 . . ? H2M1 C2M H2M2 109.5 . . ? O2M C2M H2M3 109.5 . . ? H2M1 C2M H2M3 109.5 . . ? H2M2 C2M H2M3 109.5 . . ? C2M O2M H2M 109.5 . . ? _diffrn_measured_fraction_theta_max 0.772 _diffrn_reflns_theta_full 23.52 _diffrn_measured_fraction_theta_full 0.772 _refine_diff_density_max 0.362 _refine_diff_density_min -0.761 _refine_diff_density_rms 0.082 #_vrf_REFLT03_12 #; #PROBLEM: Reflection count < 85% complete (theta max?) #RESPONSE: The structure was originally collected on a 4-circle #machine as orthorhombic P. The twinning by pseudo-merohedry #was later discovered, and we now have no crystals left for #re-analysis. #; data_13 _database_code_depnum_ccdc_archive 'CCDC 233481' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 N4 Ni O4 S2' _chemical_formula_sum 'C18 H26 N4 Ni O4 S2' _chemical_formula_weight 485.26 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' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 12.832(6) _cell_length_b 6.912(3) _cell_length_c 12.253(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.68(3) _cell_angle_gamma 90.00 _cell_volume 1029.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 20 _cell_measurement_theta_max 22 _exptl_crystal_description rod _exptl_crystal_colour Red _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 3.544 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #_vrf_PLAT057_13 #; #PROBLEM: Correction for Absorption Required RT(exp) = 1.32 #RESPONSE: The crystal was lost before psi-scan data could be collected #and we no longer have any crystals for re-analysis. There are no signs #of large systematic errors due to absorption in the refinement. #; _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe Stadi-4 4-circle diffractometer' _diffrn_measurement_method Omega-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 1546 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 60.01 _reflns_number_total 1479 _reflns_number_gt 1308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _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^)+(0.1095P)^2^+0.4448P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1479 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _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 Ni1 Ni 0.5000 0.0000 0.0000 0.0311(3) Uani 1 2 d S . . C1A C 0.8181(3) 0.2937(5) 0.0372(3) 0.0330(8) Uani 1 1 d . . . S2A S 0.67740(7) 0.26935(13) -0.04563(7) 0.0355(3) Uani 1 1 d . . . O1A O 0.6180(2) 0.4193(4) -0.0083(2) 0.0472(7) Uani 1 1 d . . . O2A O 0.6763(2) 0.2810(4) -0.1642(2) 0.0495(7) Uani 1 1 d . . . N3A N 0.6400(2) 0.0655(5) -0.0134(3) 0.0371(7) Uani 1 1 d . . . C4A C 0.6821(3) -0.0997(6) -0.0638(4) 0.0439(10) Uani 1 1 d . . . H4AA H 0.7128 -0.1987 -0.0050 0.053 Uiso 1 1 calc R . . H4BA H 0.7401 -0.0564 -0.0942 0.053 Uiso 1 1 calc R . . C5A C 0.5866(3) -0.1809(6) -0.1593(3) 0.0392(9) Uani 1 1 d . . . H5AA H 0.5653 -0.0930 -0.2255 0.047 Uiso 1 1 calc R . . H5BA H 0.6055 -0.3070 -0.1845 0.047 Uiso 1 1 calc R . . N6A N 0.4961(2) -0.2008(4) -0.1089(2) 0.0347(7) Uani 1 1 d . . . H6AA H 0.5016 -0.3177 -0.0733 0.042 Uiso 1 1 calc R . . H6BA H 0.4303 -0.1970 -0.1664 0.042 Uiso 1 1 calc R . . C7A C 0.8475(3) 0.3493(6) 0.1516(3) 0.0407(9) Uani 1 1 d . . . H7A H 0.7928 0.3733 0.1858 0.049 Uiso 1 1 calc R . . C8A C 0.9569(3) 0.3694(6) 0.2151(3) 0.0437(9) Uani 1 1 d . . . H8A H 0.9760 0.4088 0.2925 0.052 Uiso 1 1 calc R . . C9A C 1.0397(3) 0.3329(5) 0.1676(3) 0.0379(9) Uani 1 1 d . . . C10A C 1.0087(3) 0.2762(6) 0.0538(3) 0.0430(10) Uani 1 1 d . . . H10A H 1.0634 0.2502 0.0199 0.052 Uiso 1 1 calc R . . C11A C 0.8998(3) 0.2568(5) -0.0115(3) 0.0419(9) Uani 1 1 d . . . H11A H 0.8808 0.2186 -0.0890 0.050 Uiso 1 1 calc R . . C12A C 1.1593(3) 0.3562(6) 0.2385(4) 0.0488(10) Uani 1 1 d . . . H21A H 1.1984 0.4189 0.1924 0.073 Uiso 1 1 calc R . . H22A H 1.1913 0.2300 0.2629 0.073 Uiso 1 1 calc R . . H23A H 1.1648 0.4348 0.3057 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 Ni1 0.0307(5) 0.0365(6) 0.0309(5) -0.0008(3) 0.0166(4) -0.0020(3) C1A 0.0328(18) 0.0366(19) 0.035(2) 0.0011(15) 0.0187(16) -0.0026(15) S2A 0.0318(5) 0.0411(6) 0.0380(6) 0.0044(4) 0.0175(4) -0.0005(3) O1A 0.0426(15) 0.0389(15) 0.0696(19) 0.0092(14) 0.0312(13) 0.0070(12) O2A 0.0437(15) 0.073(2) 0.0342(15) 0.0100(13) 0.0159(12) -0.0041(13) N3A 0.0347(16) 0.0371(17) 0.0461(18) -0.0042(14) 0.0220(14) -0.0034(13) C4A 0.035(2) 0.047(2) 0.056(2) -0.0064(19) 0.0246(18) -0.0023(16) C5A 0.0411(19) 0.044(2) 0.040(2) -0.0029(17) 0.0231(17) -0.0006(17) N6A 0.0328(15) 0.0418(17) 0.0337(17) -0.0006(13) 0.0166(13) -0.0024(13) C7A 0.044(2) 0.050(2) 0.037(2) -0.0086(17) 0.0259(17) -0.0045(17) C8A 0.048(2) 0.051(2) 0.037(2) -0.0050(17) 0.0205(17) -0.0104(18) C9A 0.0372(19) 0.038(2) 0.041(2) -0.0014(16) 0.0153(16) -0.0043(16) C10A 0.037(2) 0.057(2) 0.044(2) -0.0054(18) 0.0240(17) -0.0011(17) C11A 0.040(2) 0.055(2) 0.038(2) -0.0058(17) 0.0231(17) -0.0024(17) C12A 0.041(2) 0.055(3) 0.048(2) -0.0024(19) 0.0114(18) -0.0038(18) _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 Ni1 N3A 1.910(3) 3_655 ? Ni1 N3A 1.910(3) . ? Ni1 N6A 1.914(3) 3_655 ? Ni1 N6A 1.914(3) . ? C1A C7A 1.384(5) . ? C1A C11A 1.385(5) . ? C1A S2A 1.774(4) . ? S2A O1A 1.445(3) . ? S2A O2A 1.450(3) . ? S2A N3A 1.579(3) . ? N3A C4A 1.480(5) . ? C4A C5A 1.506(5) . ? C4A H4AA 0.9800 . ? C4A H4BA 0.9800 . ? C5A N6A 1.486(4) . ? C5A H5AA 0.9800 . ? C5A H5BA 0.9800 . ? N6A H6AA 0.9100 . ? N6A H6BA 0.9100 . ? C7A C8A 1.378(5) . ? C7A H7A 0.9400 . ? C8A C9A 1.388(5) . ? C8A H8A 0.9400 . ? C9A C10A 1.379(5) . ? C9A C12A 1.510(5) . ? C10A C11A 1.377(6) . ? C10A H10A 0.9400 . ? C11A H11A 0.9400 . ? C12A H21A 0.9700 . ? C12A H22A 0.9700 . ? C12A H23A 0.9700 . ? 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 N3A Ni1 N3A 180.00(17) 3_655 . ? N3A Ni1 N6A 85.85(12) 3_655 3_655 ? N3A Ni1 N6A 94.15(12) . 3_655 ? N3A Ni1 N6A 94.15(12) 3_655 . ? N3A Ni1 N6A 85.85(12) . . ? N6A Ni1 N6A 180.00(17) 3_655 . ? C7A C1A C11A 119.3(3) . . ? C7A C1A S2A 120.2(3) . . ? C11A C1A S2A 120.5(3) . . ? O1A S2A O2A 116.13(17) . . ? O1A S2A N3A 109.10(16) . . ? O2A S2A N3A 113.19(17) . . ? O1A S2A C1A 107.13(17) . . ? O2A S2A C1A 104.44(15) . . ? N3A S2A C1A 106.08(16) . . ? C4A N3A S2A 113.8(2) . . ? C4A N3A Ni1 109.4(2) . . ? S2A N3A Ni1 127.06(18) . . ? N3A C4A C5A 107.3(3) . . ? N3A C4A H4AA 110.3 . . ? C5A C4A H4AA 110.3 . . ? N3A C4A H4BA 110.3 . . ? C5A C4A H4BA 110.3 . . ? H4AA C4A H4BA 108.5 . . ? N6A C5A C4A 105.2(3) . . ? N6A C5A H5AA 110.7 . . ? C4A C5A H5AA 110.7 . . ? N6A C5A H5BA 110.7 . . ? C4A C5A H5BA 110.7 . . ? H5AA C5A H5BA 108.8 . . ? C5A N6A Ni1 111.9(2) . . ? C5A N6A H6AA 109.2 . . ? Ni1 N6A H6AA 109.2 . . ? C5A N6A H6BA 109.2 . . ? Ni1 N6A H6BA 109.2 . . ? H6AA N6A H6BA 107.9 . . ? C8A C7A C1A 119.8(3) . . ? C8A C7A H7A 120.1 . . ? C1A C7A H7A 120.1 . . ? C7A C8A C9A 121.6(4) . . ? C7A C8A H8A 119.2 . . ? C9A C8A H8A 119.2 . . ? C10A C9A C8A 117.6(3) . . ? C10A C9A C12A 121.5(3) . . ? C8A C9A C12A 120.8(3) . . ? C11A C10A C9A 121.7(3) . . ? C11A C10A H10A 119.1 . . ? C9A C10A H10A 119.1 . . ? C10A C11A C1A 119.9(4) . . ? C10A C11A H11A 120.0 . . ? C1A C11A H11A 120.0 . . ? C9A C12A H21A 109.5 . . ? C9A C12A H22A 109.5 . . ? H21A C12A H22A 109.5 . . ? C9A C12A H23A 109.5 . . ? H21A C12A H23A 109.5 . . ? H22A C12A H23A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 60.01 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.592 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.099 data_16 _database_code_depnum_ccdc_archive 'CCDC 233482' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H38 Cu N4 O4 S2' _chemical_formula_sum 'C24 H38 Cu N4 O4 S2' _chemical_formula_weight 574.24 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2601(15) _cell_length_b 10.817(3) _cell_length_c 19.487(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.534(4) _cell_angle_gamma 90.00 _cell_volume 1315.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6213 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.5 _exptl_crystal_description plate _exptl_crystal_colour Purple _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 1.027 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.664 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7519 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.05 _diffrn_reflns_theta_max 26.40 _reflns_number_total 5180 _reflns_number_gt 4556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0235P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.030(10) _refine_ls_number_reflns 5180 _refine_ls_number_parameters 322 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_restrained_S_all 0.919 _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 Cu1 Cu -0.46935(5) -0.15042(3) -0.369069(18) 0.01859(9) Uani 1 1 d . . . C1A C -0.0406(4) -0.1395(3) -0.16921(14) 0.0197(6) Uani 1 1 d . . . S2A S -0.15126(12) -0.22934(7) -0.23958(4) 0.02242(18) Uani 1 1 d . . . O1A O -0.3308(3) -0.2960(2) -0.21620(11) 0.0306(5) Uani 1 1 d . . . O2A O 0.0218(3) -0.30468(19) -0.26173(11) 0.0292(5) Uani 1 1 d . . . N3A N -0.2367(4) -0.1308(2) -0.29538(12) 0.0212(6) Uani 1 1 d . . . C4A C -0.0657(5) -0.0491(3) -0.31733(16) 0.0225(7) Uani 1 1 d . . . H4AA H 0.0314 -0.0955 -0.3457 0.027 Uiso 1 1 calc R . . H4BA H 0.0195 -0.0149 -0.2767 0.027 Uiso 1 1 calc R . . C5A C -0.1758(5) 0.0533(3) -0.35875(16) 0.0247(7) Uani 1 1 d . . . H5AA H -0.2524 0.1085 -0.3284 0.030 Uiso 1 1 calc R . . H5BA H -0.0696 0.1029 -0.3819 0.030 Uiso 1 1 calc R . . N6A N -0.3284(4) -0.0053(2) -0.41012(13) 0.0215(6) Uani 1 1 d . . . H6AA H -0.2573 -0.0308 -0.4472 0.026 Uiso 1 1 calc R . . H6BA H -0.4310 0.0512 -0.4256 0.026 Uiso 1 1 calc R . . C7A C 0.1692(4) -0.1577(3) -0.14237(14) 0.0252(6) Uani 1 1 d . . . H7A H 0.2578 -0.2170 -0.1621 0.030 Uiso 1 1 calc R . . C8A C 0.2477(5) -0.0873(3) -0.08587(16) 0.0276(7) Uani 1 1 d . . . H8A H 0.3907 -0.1001 -0.0671 0.033 Uiso 1 1 calc R . . C9A C 0.1226(5) 0.0007(3) -0.05650(16) 0.0229(7) Uani 1 1 d . . . C10A C -0.0874(5) 0.0182(3) -0.08598(15) 0.0249(7) Uani 1 1 d . . . H10A H -0.1760 0.0790 -0.0674 0.030 Uiso 1 1 calc R . . C11A C -0.1668(5) -0.0515(3) -0.14136(15) 0.0236(7) Uani 1 1 d . . . H11A H -0.3095 -0.0388 -0.1604 0.028 Uiso 1 1 calc R . . C12A C 0.1967(5) 0.0758(3) 0.00732(17) 0.0273(7) Uani 1 1 d . . . C13A C 0.1635(6) 0.2143(3) -0.00677(19) 0.0465(10) Uani 1 1 d . . . H31A H 0.0113 0.2304 -0.0193 0.070 Uiso 1 1 calc R . . H32A H 0.2479 0.2396 -0.0446 0.070 Uiso 1 1 calc R . . H33A H 0.2100 0.2615 0.0347 0.070 Uiso 1 1 calc R . . C14A C 0.4340(5) 0.0552(4) 0.0294(2) 0.0477(11) Uani 1 1 d . . . H41A H 0.4741 0.1040 0.0708 0.072 Uiso 1 1 calc R . . H42A H 0.5209 0.0811 -0.0077 0.072 Uiso 1 1 calc R . . H43A H 0.4590 -0.0326 0.0393 0.072 Uiso 1 1 calc R . . C15A C 0.0652(5) 0.0384(3) 0.06742(17) 0.0347(8) Uani 1 1 d . . . H51A H -0.0851 0.0616 0.0567 0.052 Uiso 1 1 calc R . . H52A H 0.1215 0.0809 0.1094 0.052 Uiso 1 1 calc R . . H53A H 0.0753 -0.0512 0.0744 0.052 Uiso 1 1 calc R . . C1B C -0.6925(5) -0.1119(2) -0.57604(15) 0.0197(7) Uani 1 1 d . . . S2B S -0.80284(11) -0.07072(7) -0.49776(4) 0.01938(17) Uani 1 1 d . . . O1B O -0.7272(3) 0.05345(18) -0.48178(10) 0.0227(5) Uani 1 1 d . . . O2B O -1.0333(3) -0.08240(19) -0.51161(10) 0.0246(5) Uani 1 1 d . . . N3B N -0.7131(3) -0.1626(3) -0.44059(11) 0.0199(5) Uani 1 1 d . . . C4B C -0.8262(5) -0.2830(3) -0.44111(16) 0.0226(7) Uani 1 1 d . . . H4AB H -0.8609 -0.3115 -0.4890 0.027 Uiso 1 1 calc R . . H4BB H -0.9612 -0.2755 -0.4182 0.027 Uiso 1 1 calc R . . C5B C -0.6765(5) -0.3731(3) -0.40267(15) 0.0220(7) Uani 1 1 d . . . H5AB H -0.7550 -0.4487 -0.3911 0.026 Uiso 1 1 calc R . . H5BB H -0.5592 -0.3967 -0.4313 0.026 Uiso 1 1 calc R . . N6B N -0.5886(4) -0.3107(2) -0.33921(13) 0.0236(6) Uani 1 1 d . . . H6AB H -0.4827 -0.3580 -0.3168 0.028 Uiso 1 1 calc R . . H6BB H -0.6947 -0.2974 -0.3100 0.028 Uiso 1 1 calc R . . C7B C -0.7831(5) -0.0634(3) -0.63773(15) 0.0239(7) Uani 1 1 d . . . H7B H -0.9076 -0.0131 -0.6381 0.029 Uiso 1 1 calc R . . C8B C -0.6923(4) -0.0885(3) -0.69815(16) 0.0238(7) Uani 1 1 d . . . H8B H -0.7550 -0.0545 -0.7399 0.029 Uiso 1 1 calc R . . C9B C -0.5100(4) -0.1629(3) -0.69976(14) 0.0203(6) Uani 1 1 d . . . C10B C -0.4211(5) -0.2097(3) -0.63753(16) 0.0226(7) Uani 1 1 d . . . H10B H -0.2965 -0.2600 -0.6369 0.027 Uiso 1 1 calc R . . C11B C -0.5114(5) -0.1844(2) -0.57595(15) 0.0202(7) Uani 1 1 d . . . H11B H -0.4481 -0.2170 -0.5339 0.024 Uiso 1 1 calc R . . C12B C -0.4149(5) -0.1881(3) -0.76862(16) 0.0247(7) Uani 1 1 d . . . C13B C -0.5930(5) -0.2354(4) -0.82024(17) 0.0386(9) Uani 1 1 d . . . H31B H -0.7029 -0.1714 -0.8281 0.058 Uiso 1 1 calc R . . H32B H -0.6573 -0.3098 -0.8019 0.058 Uiso 1 1 calc R . . H33B H -0.5327 -0.2554 -0.8638 0.058 Uiso 1 1 calc R . . C14B C -0.2399(6) -0.2862(4) -0.76202(18) 0.0404(10) Uani 1 1 d . . . H41B H -0.1885 -0.3023 -0.8074 0.061 Uiso 1 1 calc R . . H42B H -0.2979 -0.3626 -0.7438 0.061 Uiso 1 1 calc R . . H43B H -0.1208 -0.2567 -0.7306 0.061 Uiso 1 1 calc R . . C15B C -0.3197(5) -0.0679(4) -0.79468(18) 0.0373(8) Uani 1 1 d . . . H51B H -0.4315 -0.0044 -0.7996 0.056 Uiso 1 1 calc R . . H52B H -0.2632 -0.0827 -0.8394 0.056 Uiso 1 1 calc R . . H53B H -0.2035 -0.0399 -0.7617 0.056 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 Cu1 0.01639(16) 0.01862(17) 0.02026(18) 0.00081(17) -0.00168(13) -0.00165(16) C1A 0.0220(14) 0.0197(15) 0.0171(15) 0.0063(15) -0.0008(11) -0.0055(14) S2A 0.0247(4) 0.0214(4) 0.0202(4) 0.0009(3) -0.0041(3) -0.0032(3) O1A 0.0310(13) 0.0345(13) 0.0249(13) 0.0111(10) -0.0076(10) -0.0123(11) O2A 0.0330(13) 0.0267(12) 0.0271(13) -0.0035(10) -0.0036(10) 0.0044(10) N3A 0.0197(12) 0.0264(15) 0.0168(13) 0.0048(12) -0.0027(10) -0.0046(12) C4A 0.0178(16) 0.0260(17) 0.0233(17) 0.0001(14) -0.0017(13) -0.0056(13) C5A 0.0253(17) 0.0230(16) 0.0249(18) 0.0010(14) -0.0048(15) -0.0025(14) N6A 0.0171(13) 0.0210(13) 0.0261(15) 0.0043(11) 0.0004(11) -0.0038(11) C7A 0.0222(14) 0.0268(16) 0.0263(16) 0.0005(17) 0.0010(12) 0.0031(16) C8A 0.0212(16) 0.0352(19) 0.0258(19) -0.0020(15) -0.0014(14) 0.0045(15) C9A 0.0216(17) 0.0253(16) 0.0221(18) 0.0010(14) 0.0030(14) -0.0038(14) C10A 0.0262(17) 0.0274(17) 0.0215(18) -0.0014(14) 0.0041(14) 0.0063(14) C11A 0.0167(15) 0.0305(18) 0.0232(18) 0.0070(14) -0.0004(13) 0.0029(13) C12A 0.0242(17) 0.0323(18) 0.0254(18) -0.0067(15) 0.0021(14) -0.0061(14) C13A 0.068(3) 0.034(2) 0.037(2) -0.0056(17) 0.002(2) -0.008(2) C14A 0.028(2) 0.073(3) 0.041(2) -0.023(2) -0.0048(18) -0.0036(19) C15A 0.039(2) 0.040(2) 0.0248(19) -0.0038(16) -0.0009(16) -0.0070(16) C1B 0.0200(16) 0.0174(16) 0.0215(17) -0.0022(12) 0.0010(13) -0.0044(12) S2B 0.0165(4) 0.0205(4) 0.0206(4) 0.0006(3) -0.0015(3) 0.0010(3) O1B 0.0220(11) 0.0196(11) 0.0260(12) 0.0019(9) -0.0023(10) 0.0026(9) O2B 0.0149(10) 0.0328(12) 0.0258(12) 0.0018(10) -0.0005(9) 0.0025(9) N3B 0.0193(12) 0.0188(13) 0.0208(13) 0.0037(13) -0.0030(10) -0.0044(12) C4B 0.0188(16) 0.0236(17) 0.0247(18) 0.0011(14) -0.0020(14) -0.0050(13) C5B 0.0227(16) 0.0182(16) 0.0246(18) 0.0010(13) -0.0019(14) -0.0029(13) N6B 0.0201(13) 0.0193(13) 0.0308(16) 0.0055(12) -0.0021(12) -0.0025(11) C7B 0.0215(16) 0.0259(16) 0.0236(17) 0.0019(14) -0.0021(13) 0.0039(14) C8B 0.0224(16) 0.0261(16) 0.0221(18) 0.0019(14) -0.0032(14) -0.0010(13) C9B 0.0201(14) 0.0183(16) 0.0223(16) -0.0018(14) 0.0001(12) -0.0036(14) C10B 0.0191(16) 0.0199(16) 0.0288(19) -0.0017(14) 0.0011(14) 0.0014(13) C11B 0.0222(16) 0.0175(16) 0.0198(17) 0.0008(12) -0.0046(13) -0.0019(12) C12B 0.0264(17) 0.0254(18) 0.0223(18) -0.0003(13) 0.0026(14) 0.0028(13) C13B 0.040(2) 0.043(2) 0.032(2) -0.0079(18) 0.0003(17) -0.0070(18) C14B 0.044(2) 0.053(2) 0.026(2) 0.0004(18) 0.0106(17) 0.022(2) C15B 0.037(2) 0.038(2) 0.038(2) -0.0014(18) 0.0118(17) -0.0014(17) _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 Cu1 N3A 1.974(2) . ? Cu1 N3B 1.988(2) . ? Cu1 N6B 1.992(2) . ? Cu1 N6A 1.998(2) . ? C1A C11A 1.376(4) . ? C1A C7A 1.389(4) . ? C1A S2A 1.776(3) . ? S2A O1A 1.440(2) . ? S2A O2A 1.448(2) . ? S2A N3A 1.585(3) . ? N3A C4A 1.478(4) . ? C4A C5A 1.505(4) . ? C4A H4AA 0.9900 . ? C4A H4BA 0.9900 . ? C5A N6A 1.472(4) . ? C5A H5AA 0.9900 . ? C5A H5BA 0.9900 . ? N6A H6AA 0.9200 . ? N6A H6BA 0.9200 . ? C7A C8A 1.396(4) . ? C7A H7A 0.9500 . ? C8A C9A 1.385(4) . ? C8A H8A 0.9500 . ? C9A C10A 1.405(4) . ? C9A C12A 1.526(4) . ? C10A C11A 1.377(4) . ? C10A H10A 0.9500 . ? C11A H11A 0.9500 . ? C12A C14A 1.530(4) . ? C12A C13A 1.535(5) . ? C12A C15A 1.538(4) . ? C13A H31A 0.9800 . ? C13A H32A 0.9800 . ? C13A H33A 0.9800 . ? C14A H41A 0.9800 . ? C14A H42A 0.9800 . ? C14A H43A 0.9800 . ? C15A H51A 0.9800 . ? C15A H52A 0.9800 . ? C15A H53A 0.9800 . ? C1B C11B 1.378(4) . ? C1B C7B 1.391(4) . ? C1B S2B 1.780(3) . ? S2B O1B 1.450(2) . ? S2B O2B 1.452(2) . ? S2B N3B 1.564(2) . ? N3B C4B 1.483(4) . ? C4B C5B 1.509(4) . ? C4B H4AB 0.9900 . ? C4B H4BB 0.9900 . ? C5B N6B 1.477(4) . ? C5B H5AB 0.9900 . ? C5B H5BB 0.9900 . ? N6B H6AB 0.9200 . ? N6B H6BB 0.9200 . ? C7B C8B 1.375(4) . ? C7B H7B 0.9500 . ? C8B C9B 1.398(4) . ? C8B H8B 0.9500 . ? C9B C10B 1.389(4) . ? C9B C12B 1.535(4) . ? C10B C11B 1.394(4) . ? C10B H10B 0.9500 . ? C11B H11B 0.9500 . ? C12B C14B 1.523(4) . ? C12B C13B 1.529(4) . ? C12B C15B 1.533(4) . ? C13B H31B 0.9800 . ? C13B H32B 0.9800 . ? C13B H33B 0.9800 . ? C14B H41B 0.9800 . ? C14B H42B 0.9800 . ? C14B H43B 0.9800 . ? C15B H51B 0.9800 . ? C15B H52B 0.9800 . ? C15B H53B 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 N3A Cu1 N3B 176.66(12) . . ? N3A Cu1 N6B 98.78(10) . . ? N3B Cu1 N6B 82.11(10) . . ? N3A Cu1 N6A 83.30(10) . . ? N3B Cu1 N6A 96.31(10) . . ? N6B Cu1 N6A 171.02(11) . . ? C11A C1A C7A 120.3(3) . . ? C11A C1A S2A 118.8(2) . . ? C7A C1A S2A 120.9(3) . . ? O1A S2A O2A 115.69(13) . . ? O1A S2A N3A 108.92(12) . . ? O2A S2A N3A 113.19(13) . . ? O1A S2A C1A 107.25(13) . . ? O2A S2A C1A 106.41(13) . . ? N3A S2A C1A 104.58(14) . . ? C4A N3A S2A 112.82(18) . . ? C4A N3A Cu1 111.31(18) . . ? S2A N3A Cu1 128.07(15) . . ? N3A C4A C5A 106.5(2) . . ? N3A C4A H4AA 110.4 . . ? C5A C4A H4AA 110.4 . . ? N3A C4A H4BA 110.4 . . ? C5A C4A H4BA 110.4 . . ? H4AA C4A H4BA 108.6 . . ? N6A C5A C4A 107.1(2) . . ? N6A C5A H5AA 110.3 . . ? C4A C5A H5AA 110.3 . . ? N6A C5A H5BA 110.3 . . ? C4A C5A H5BA 110.3 . . ? H5AA C5A H5BA 108.6 . . ? C5A N6A Cu1 110.45(19) . . ? C5A N6A H6AA 109.6 . . ? Cu1 N6A H6AA 109.6 . . ? C5A N6A H6BA 109.6 . . ? Cu1 N6A H6BA 109.6 . . ? H6AA N6A H6BA 108.1 . . ? C1A C7A C8A 118.9(3) . . ? C1A C7A H7A 120.5 . . ? C8A C7A H7A 120.5 . . ? C9A C8A C7A 121.7(3) . . ? C9A C8A H8A 119.1 . . ? C7A C8A H8A 119.1 . . ? C8A C9A C10A 117.7(3) . . ? C8A C9A C12A 123.9(3) . . ? C10A C9A C12A 118.4(3) . . ? C11A C10A C9A 121.0(3) . . ? C11A C10A H10A 119.5 . . ? C9A C10A H10A 119.5 . . ? C1A C11A C10A 120.3(3) . . ? C1A C11A H11A 119.8 . . ? C10A C11A H11A 119.8 . . ? C9A C12A C14A 112.2(3) . . ? C9A C12A C13A 110.2(3) . . ? C14A C12A C13A 107.9(3) . . ? C9A C12A C15A 109.5(3) . . ? C14A C12A C15A 108.3(3) . . ? C13A C12A C15A 108.7(3) . . ? C12A C13A H31A 109.5 . . ? C12A C13A H32A 109.5 . . ? H31A C13A H32A 109.5 . . ? C12A C13A H33A 109.5 . . ? H31A C13A H33A 109.5 . . ? H32A C13A H33A 109.5 . . ? C12A C14A H41A 109.5 . . ? C12A C14A H42A 109.5 . . ? H41A C14A H42A 109.5 . . ? C12A C14A H43A 109.5 . . ? H41A C14A H43A 109.5 . . ? H42A C14A H43A 109.5 . . ? C12A C15A H51A 109.5 . . ? C12A C15A H52A 109.5 . . ? H51A C15A H52A 109.5 . . ? C12A C15A H53A 109.5 . . ? H51A C15A H53A 109.5 . . ? H52A C15A H53A 109.5 . . ? C11B C1B C7B 119.7(3) . . ? C11B C1B S2B 121.1(2) . . ? C7B C1B S2B 119.2(2) . . ? O1B S2B O2B 115.06(12) . . ? O1B S2B N3B 110.04(13) . . ? O2B S2B N3B 111.90(13) . . ? O1B S2B C1B 105.88(13) . . ? O2B S2B C1B 105.42(13) . . ? N3B S2B C1B 108.03(13) . . ? C4B N3B S2B 114.14(18) . . ? C4B N3B Cu1 113.74(18) . . ? S2B N3B Cu1 132.08(16) . . ? N3B C4B C5B 106.6(2) . . ? N3B C4B H4AB 110.4 . . ? C5B C4B H4AB 110.4 . . ? N3B C4B H4BB 110.4 . . ? C5B C4B H4BB 110.4 . . ? H4AB C4B H4BB 108.6 . . ? N6B C5B C4B 107.2(2) . . ? N6B C5B H5AB 110.3 . . ? C4B C5B H5AB 110.3 . . ? N6B C5B H5BB 110.3 . . ? C4B C5B H5BB 110.3 . . ? H5AB C5B H5BB 108.5 . . ? C5B N6B Cu1 106.05(18) . . ? C5B N6B H6AB 110.5 . . ? Cu1 N6B H6AB 110.5 . . ? C5B N6B H6BB 110.5 . . ? Cu1 N6B H6BB 110.5 . . ? H6AB N6B H6BB 108.7 . . ? C8B C7B C1B 119.9(3) . . ? C8B C7B H7B 120.1 . . ? C1B C7B H7B 120.1 . . ? C7B C8B C9B 121.8(3) . . ? C7B C8B H8B 119.1 . . ? C9B C8B H8B 119.1 . . ? C10B C9B C8B 117.5(3) . . ? C10B C9B C12B 122.8(3) . . ? C8B C9B C12B 119.7(3) . . ? C9B C10B C11B 121.2(3) . . ? C9B C10B H10B 119.4 . . ? C11B C10B H10B 119.4 . . ? C1B C11B C10B 120.0(3) . . ? C1B C11B H11B 120.0 . . ? C10B C11B H11B 120.0 . . ? C14B C12B C13B 107.7(3) . . ? C14B C12B C15B 108.8(3) . . ? C13B C12B C15B 110.4(3) . . ? C14B C12B C9B 112.1(3) . . ? C13B C12B C9B 108.8(3) . . ? C15B C12B C9B 109.1(3) . . ? C12B C13B H31B 109.5 . . ? C12B C13B H32B 109.5 . . ? H31B C13B H32B 109.5 . . ? C12B C13B H33B 109.5 . . ? H31B C13B H33B 109.5 . . ? H32B C13B H33B 109.5 . . ? C12B C14B H41B 109.5 . . ? C12B C14B H42B 109.5 . . ? H41B C14B H42B 109.5 . . ? C12B C14B H43B 109.5 . . ? H41B C14B H43B 109.5 . . ? H42B C14B H43B 109.5 . . ? C12B C15B H51B 109.5 . . ? C12B C15B H52B 109.5 . . ? H51B C15B H52B 109.5 . . ? C12B C15B H53B 109.5 . . ? H51B C15B H53B 109.5 . . ? H52B C15B H53B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.616 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.059