data_global _journal_date_recd_electronic 2015-11-18 _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted 2016-01-11 _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ED5007 _journal_coeditor_notes ; ? ; _journal_paper_category FA _journal_techeditor_code M160054 _iucr_compatibility_tag ACTA95 _journal_techeditor_notes ; ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? data_ACZ2HP11 _database_code_depnum_ccdc_archive 'CCDC 1436985' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE;2 PYRIDONE' _chemical_melting_point 453 _chemical_formula_moiety 'C4H6N4O3S2,C5H5NO' _chemical_formula_sum 'C9 H11 N5 O4 S2' _chemical_formula_weight 317.35 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)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.9138(4) _cell_length_b 33.192(3) _cell_length_c 8.3659(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.5200(10) _cell_angle_gamma 90.00 _cell_volume 1345.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6192 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 25.94 _exptl_crystal_description needle _exptl_crystal_colour COLORLES _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.417 _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 298(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 13846 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2640 _reflns_number_gt 2176 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.2415P] 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 2640 _refine_ls_number_parameters 198 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.048 _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 S1 S -0.15925(10) 0.228595(15) 0.67680(6) 0.03577(16) Uani 1 1 d . . . S2 S -0.07309(10) 0.137123(16) 0.65477(6) 0.04162(17) Uani 1 1 d . . . N1 N 0.2548(3) 0.18467(5) 0.8351(2) 0.0383(4) Uani 1 1 d . . . N3 N 0.3114(4) 0.08084(5) 0.7764(2) 0.0448(4) Uani 1 1 d . . . N4 N -0.2949(4) 0.24391(6) 0.8236(2) 0.0385(4) Uani 1 1 d . . . C1 C 0.0263(4) 0.18371(6) 0.7336(2) 0.0339(4) Uani 1 1 d . . . O2 O -0.3746(3) 0.21585(5) 0.55101(18) 0.0548(4) Uani 1 1 d . . . C2 C 0.2258(4) 0.11980(6) 0.7721(2) 0.0367(4) Uani 1 1 d . . . N2 N 0.3729(3) 0.14739(5) 0.8588(2) 0.0402(4) Uani 1 1 d . . . O3 O 0.0387(3) 0.25754(5) 0.64635(19) 0.0518(4) Uani 1 1 d . . . O1 O -0.0546(4) 0.05834(5) 0.6013(2) 0.0689(5) Uani 1 1 d . . . O4 O -0.2082(3) 0.06497(5) -0.0152(2) 0.0612(5) Uani 1 1 d . . . C5 C -0.0597(4) 0.08755(7) 0.0815(3) 0.0478(5) Uani 1 1 d . . . N5 N -0.1277(4) 0.12714(6) 0.0950(2) 0.0467(5) Uani 1 1 d D . . C4 C 0.2896(7) 0.01022(8) 0.7138(4) 0.0812(9) Uani 1 1 d . . . H4A H 0.2667 0.0000 0.8180 0.122 Uiso 1 1 calc R . . H4B H 0.4827 0.0120 0.7079 0.122 Uiso 1 1 calc R . . H4C H 0.2011 -0.0076 0.6306 0.122 Uiso 1 1 calc R . . C6 C 0.1882(5) 0.07568(8) 0.1854(3) 0.0597(7) Uani 1 1 d . . . H6 H 0.2478 0.0491 0.1834 0.072 Uiso 1 1 calc R . . C3 C 0.1627(5) 0.05098(7) 0.6901(3) 0.0538(6) Uani 1 1 d . . . C8 C 0.2571(6) 0.14215(9) 0.2911(3) 0.0648(7) Uani 1 1 d . . . H8 H 0.3630 0.1604 0.3591 0.078 Uiso 1 1 calc R . . C9 C 0.0223(5) 0.15392(8) 0.1954(3) 0.0565(6) Uani 1 1 d . . . H9 H -0.0367 0.1805 0.1983 0.068 Uiso 1 1 calc R . . C7 C 0.3371(5) 0.10210(9) 0.2859(3) 0.0648(7) Uani 1 1 d . . . H7 H 0.4962 0.0934 0.3531 0.078 Uiso 1 1 calc R . . H4D H -0.186(5) 0.2539(6) 0.899(3) 0.038(6) Uiso 1 1 d . . . H4E H -0.432(5) 0.2307(7) 0.842(3) 0.049(7) Uiso 1 1 d . . . H3A H 0.470(6) 0.0766(8) 0.845(3) 0.061(7) Uiso 1 1 d . . . H5A H -0.274(4) 0.1352(7) 0.034(3) 0.056(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0334(3) 0.0423(3) 0.0300(3) 0.0022(2) 0.00046(19) 0.0064(2) S2 0.0339(3) 0.0442(3) 0.0426(3) -0.0087(2) -0.0061(2) 0.0019(2) N1 0.0317(8) 0.0365(9) 0.0435(10) 0.0006(7) -0.0031(7) 0.0013(7) N3 0.0363(10) 0.0374(10) 0.0568(11) -0.0055(8) -0.0042(9) 0.0015(8) N4 0.0299(9) 0.0454(10) 0.0398(10) -0.0078(8) 0.0046(8) -0.0050(8) C1 0.0298(10) 0.0383(11) 0.0328(10) -0.0007(8) 0.0028(8) 0.0017(8) O2 0.0542(10) 0.0625(10) 0.0398(8) -0.0094(7) -0.0152(7) 0.0179(8) C2 0.0301(10) 0.0390(11) 0.0401(11) -0.0019(9) 0.0030(8) 0.0003(8) N2 0.0308(9) 0.0350(9) 0.0512(10) -0.0012(7) -0.0040(7) 0.0011(7) O3 0.0510(9) 0.0525(10) 0.0552(9) 0.0173(7) 0.0187(7) 0.0040(7) O1 0.0629(11) 0.0560(11) 0.0777(12) -0.0198(9) -0.0180(9) 0.0010(9) O4 0.0505(9) 0.0490(9) 0.0770(12) -0.0027(8) -0.0104(9) 0.0052(8) C5 0.0386(12) 0.0516(14) 0.0517(13) 0.0047(10) 0.0034(10) 0.0007(10) N5 0.0366(10) 0.0481(11) 0.0525(11) 0.0055(9) -0.0008(9) 0.0022(8) C4 0.084(2) 0.0406(14) 0.108(2) -0.0138(15) -0.0140(18) 0.0017(13) C6 0.0455(13) 0.0599(16) 0.0703(16) 0.0125(13) -0.0007(12) 0.0113(12) C3 0.0535(14) 0.0426(13) 0.0624(15) -0.0095(11) 0.0014(12) -0.0022(11) C8 0.0540(15) 0.0794(19) 0.0569(15) -0.0052(13) -0.0032(12) -0.0074(14) C9 0.0548(15) 0.0549(15) 0.0582(14) -0.0029(12) 0.0049(12) -0.0046(12) C7 0.0461(14) 0.085(2) 0.0580(16) 0.0100(14) -0.0086(12) 0.0007(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 S1 O3 1.4199(16) . ? S1 O2 1.4274(15) . ? S1 N4 1.5753(18) . ? S1 C1 1.7701(19) . ? S2 C1 1.7197(19) . ? S2 C2 1.725(2) . ? N1 C1 1.291(2) . ? N1 N2 1.367(2) . ? N3 C2 1.359(3) . ? N3 C3 1.365(3) . ? N3 H3A 0.90(3) . ? N4 H4D 0.83(2) . ? N4 H4E 0.84(3) . ? C2 N2 1.309(2) . ? O1 C3 1.221(3) . ? O4 C5 1.246(3) . ? C5 N5 1.365(3) . ? C5 C6 1.430(3) . ? N5 C9 1.354(3) . ? N5 H5A 0.853(16) . ? C4 C3 1.489(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C6 C7 1.345(4) . ? C6 H6 0.9300 . ? C8 C9 1.349(4) . ? C8 C7 1.389(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C7 H7 0.9300 . ? 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 O3 S1 O2 120.96(10) . . ? O3 S1 N4 108.20(10) . . ? O2 S1 N4 108.22(10) . . ? O3 S1 C1 106.26(9) . . ? O2 S1 C1 103.56(9) . . ? N4 S1 C1 109.15(9) . . ? C1 S2 C2 85.44(9) . . ? C1 N1 N2 112.04(16) . . ? C2 N3 C3 122.72(19) . . ? C2 N3 H3A 113.5(17) . . ? C3 N3 H3A 123.7(17) . . ? S1 N4 H4D 115.1(15) . . ? S1 N4 H4E 115.2(16) . . ? H4D N4 H4E 121(2) . . ? N1 C1 S2 115.80(14) . . ? N1 C1 S1 120.59(15) . . ? S2 C1 S1 123.57(11) . . ? N2 C2 N3 120.73(18) . . ? N2 C2 S2 114.98(15) . . ? N3 C2 S2 124.29(15) . . ? C2 N2 N1 111.74(16) . . ? O4 C5 N5 120.5(2) . . ? O4 C5 C6 125.3(2) . . ? N5 C5 C6 114.2(2) . . ? C9 N5 C5 124.6(2) . . ? C9 N5 H5A 118.8(17) . . ? C5 N5 H5A 116.6(17) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C7 C6 C5 121.4(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? O1 C3 N3 121.0(2) . . ? O1 C3 C4 124.6(2) . . ? N3 C3 C4 114.4(2) . . ? C9 C8 C7 118.5(2) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 N5 120.2(2) . . ? C8 C9 H9 119.9 . . ? N5 C9 H9 119.9 . . ? C6 C7 C8 121.1(2) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.351 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.053 data_ACZ2HP12 _database_code_depnum_ccdc_archive 'CCDC 1436984' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE;2 PYRIDONE' _chemical_melting_point 433 _chemical_formula_moiety 'C4H6N4O3S2,2(C5H5NO)' _chemical_formula_sum 'C14 H16 N6 O5 S2' _chemical_formula_weight 412.45 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8501(3) _cell_length_b 11.3563(6) _cell_length_c 12.3387(8) _cell_angle_alpha 82.288(5) _cell_angle_beta 81.856(4) _cell_angle_gamma 75.804(4) _cell_volume 916.20(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3198 _cell_measurement_theta_min 5.1430 _cell_measurement_theta_max 71.8840 _exptl_crystal_description block _exptl_crystal_colour colorles _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 3.005 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.13683 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5007 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 67.07 _reflns_number_total 3268 _reflns_number_gt 3035 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1265P)^2^+0.4073P] 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 3268 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1674 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.24089(9) 0.05772(5) 0.95947(5) 0.0335(2) Uani 1 1 d . . . S2 S 0.30061(10) 0.06609(5) 0.70910(5) 0.0379(2) Uani 1 1 d . . . O1 O 0.1813(3) 0.01581(17) 1.18019(17) 0.0462(5) Uani 1 1 d . . . O4 O 0.0236(3) 0.64656(18) 0.43750(17) 0.0493(5) Uani 1 1 d . . . O5 O 0.1665(4) 0.43570(19) 0.17745(18) 0.0543(6) Uani 1 1 d . . . N6 N 0.2348(3) 0.5258(2) 0.00544(18) 0.0368(5) Uani 1 1 d . . . N3 N 0.2022(3) 0.2086(2) 1.12119(19) 0.0360(5) Uani 1 1 d . . . N1 N 0.2786(3) 0.2507(2) 0.83158(19) 0.0383(5) Uani 1 1 d . . . N2 N 0.2504(3) 0.28428(19) 0.93644(19) 0.0376(5) Uani 1 1 d . . . O2 O 0.3320(4) -0.06083(18) 0.74606(18) 0.0517(5) Uani 1 1 d . . . C11 C 0.2201(4) 0.6368(2) 0.1559(2) 0.0398(6) Uani 1 1 d . . . H11 H 0.2011 0.6435 0.2312 0.048 Uiso 1 1 calc R . . N5 N 0.1912(4) 0.5326(2) 0.57629(18) 0.0393(5) Uani 1 1 d . . . C5 C 0.1597(4) 0.6322(2) 0.4996(2) 0.0363(6) Uani 1 1 d . . . N4 N 0.0888(4) 0.1104(2) 0.6619(2) 0.0445(6) Uani 1 1 d . . . O3 O 0.4477(3) 0.1111(2) 0.63316(19) 0.0592(6) Uani 1 1 d . . . C10 C 0.2042(4) 0.5270(2) 0.1168(2) 0.0360(5) Uani 1 1 d . . . C3 C 0.1763(4) 0.1184(2) 1.2020(2) 0.0376(6) Uani 1 1 d . . . C2 C 0.2298(3) 0.1931(2) 1.0117(2) 0.0311(5) Uani 1 1 d . . . C6 C 0.2904(4) 0.7128(3) 0.4969(3) 0.0450(6) Uani 1 1 d . . . H6 H 0.2762 0.7825 0.4470 0.054 Uiso 1 1 calc R . . C1 C 0.2781(4) 0.1371(2) 0.8312(2) 0.0325(5) Uani 1 1 d . . . C13 C 0.2904(4) 0.7245(2) -0.0287(3) 0.0428(6) Uani 1 1 d . . . H13 H 0.3188 0.7897 -0.0775 0.051 Uiso 1 1 calc R . . C14 C 0.2752(4) 0.6207(3) -0.0661(2) 0.0418(6) Uani 1 1 d . . . H14 H 0.2925 0.6144 -0.1414 0.050 Uiso 1 1 calc R . . C8 C 0.4615(5) 0.5844(3) 0.6420(2) 0.0499(7) Uani 1 1 d . . . H8 H 0.5612 0.5681 0.6894 0.060 Uiso 1 1 calc R . . C12 C 0.2625(4) 0.7313(2) 0.0845(3) 0.0415(6) Uani 1 1 d . . . H12 H 0.2732 0.8017 0.1116 0.050 Uiso 1 1 calc R . . C7 C 0.4350(5) 0.6892(3) 0.5661(3) 0.0489(7) Uani 1 1 d . . . H7 H 0.5183 0.7433 0.5633 0.059 Uiso 1 1 calc R . . C4 C 0.1405(5) 0.1532(3) 1.3167(3) 0.0536(8) Uani 1 1 d . . . H4C H 0.0082 0.1445 1.3493 0.080 Uiso 1 1 calc R . . H4D H 0.1489 0.2365 1.3154 0.080 Uiso 1 1 calc R . . H4E H 0.2412 0.1010 1.3593 0.080 Uiso 1 1 calc R . . C9 C 0.3372(5) 0.5079(3) 0.6441(2) 0.0483(7) Uani 1 1 d . . . H9 H 0.3528 0.4372 0.6929 0.058 Uiso 1 1 calc R . . H5A H 0.118(5) 0.483(3) 0.580(3) 0.046(9) Uiso 1 1 d . . . H4A H 0.058(5) 0.183(4) 0.638(3) 0.058(10) Uiso 1 1 d . . . H4B H -0.001(6) 0.078(4) 0.706(4) 0.066(11) Uiso 1 1 d . . . H6A H 0.229(5) 0.457(4) -0.022(3) 0.057(10) Uiso 1 1 d . . . H3A H 0.191(5) 0.281(3) 1.138(3) 0.039(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0420(4) 0.0222(3) 0.0378(4) -0.0009(2) -0.0054(3) -0.0110(2) S2 0.0474(4) 0.0313(4) 0.0352(4) -0.0009(3) -0.0011(3) -0.0129(3) O1 0.0681(13) 0.0304(10) 0.0434(10) -0.0038(8) 0.0001(9) -0.0213(9) O4 0.0629(12) 0.0402(11) 0.0526(12) 0.0106(9) -0.0240(10) -0.0252(9) O5 0.0881(16) 0.0351(11) 0.0444(11) -0.0036(8) -0.0035(10) -0.0256(10) N6 0.0469(12) 0.0279(11) 0.0395(11) -0.0074(9) -0.0082(9) -0.0118(9) N3 0.0426(11) 0.0251(11) 0.0437(12) -0.0046(9) -0.0086(9) -0.0115(8) N1 0.0475(12) 0.0304(11) 0.0410(12) 0.0035(9) -0.0103(9) -0.0175(9) N2 0.0475(12) 0.0263(10) 0.0436(12) 0.0005(8) -0.0113(9) -0.0159(9) O2 0.0728(13) 0.0297(10) 0.0496(11) -0.0035(8) -0.0059(10) -0.0069(9) C11 0.0491(14) 0.0316(13) 0.0415(14) -0.0113(11) -0.0100(11) -0.0079(11) N5 0.0505(13) 0.0363(12) 0.0343(11) 0.0019(9) -0.0057(9) -0.0189(10) C5 0.0456(14) 0.0327(13) 0.0331(12) -0.0023(10) -0.0032(10) -0.0151(11) N4 0.0606(15) 0.0363(13) 0.0419(13) 0.0039(10) -0.0148(11) -0.0206(11) O3 0.0605(13) 0.0655(15) 0.0512(13) -0.0013(11) 0.0125(10) -0.0273(11) C10 0.0410(13) 0.0298(12) 0.0395(13) -0.0054(10) -0.0093(10) -0.0089(10) C3 0.0378(12) 0.0328(13) 0.0437(14) -0.0062(10) -0.0030(10) -0.0107(10) C2 0.0297(11) 0.0230(11) 0.0432(13) -0.0006(9) -0.0099(9) -0.0093(8) C6 0.0529(15) 0.0373(14) 0.0485(15) 0.0048(11) -0.0088(12) -0.0203(12) C1 0.0344(11) 0.0282(12) 0.0375(13) 0.0004(9) -0.0082(9) -0.0116(9) C13 0.0458(14) 0.0281(13) 0.0536(16) 0.0033(11) -0.0054(12) -0.0109(11) C14 0.0489(15) 0.0369(14) 0.0388(14) -0.0055(11) -0.0058(11) -0.0071(11) C8 0.0549(17) 0.0600(19) 0.0384(14) -0.0015(13) -0.0130(12) -0.0180(14) C12 0.0415(13) 0.0264(12) 0.0601(17) -0.0106(11) -0.0113(12) -0.0078(10) C7 0.0516(16) 0.0532(17) 0.0495(16) -0.0025(13) -0.0084(13) -0.0262(13) C4 0.071(2) 0.0458(16) 0.0443(17) -0.0100(13) 0.0043(14) -0.0181(14) C9 0.0625(17) 0.0483(16) 0.0348(14) 0.0041(12) -0.0103(12) -0.0157(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 S1 C2 1.726(2) . ? S1 C1 1.731(3) . ? S2 O3 1.418(2) . ? S2 O2 1.425(2) . ? S2 N4 1.581(3) . ? S2 C1 1.773(3) . ? O1 C3 1.222(3) . ? O4 C5 1.256(3) . ? O5 C10 1.253(3) . ? N6 C14 1.356(4) . ? N6 C10 1.361(4) . ? N6 H6A 0.90(4) . ? N3 C3 1.356(4) . ? N3 C2 1.366(4) . ? N3 H3A 0.85(3) . ? N1 C1 1.292(3) . ? N1 N2 1.372(3) . ? N2 C2 1.316(3) . ? C11 C12 1.356(4) . ? C11 C10 1.429(4) . ? C11 H11 0.9300 . ? N5 C9 1.347(4) . ? N5 C5 1.368(3) . ? N5 H5A 0.84(4) . ? C5 C6 1.423(4) . ? N4 H4A 0.83(4) . ? N4 H4B 0.88(4) . ? C3 C4 1.491(4) . ? C6 C7 1.352(4) . ? C6 H6 0.9300 . ? C13 C14 1.354(4) . ? C13 C12 1.393(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C8 C9 1.353(5) . ? C8 C7 1.403(4) . ? C8 H8 0.9300 . ? C12 H12 0.9300 . ? C7 H7 0.9300 . ? C4 H4C 0.9600 . ? C4 H4D 0.9600 . ? C4 H4E 0.9600 . ? C9 H9 0.9300 . ? 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 C2 S1 C1 85.81(12) . . ? O3 S2 O2 120.57(14) . . ? O3 S2 N4 108.47(15) . . ? O2 S2 N4 108.92(14) . . ? O3 S2 C1 107.07(13) . . ? O2 S2 C1 104.15(12) . . ? N4 S2 C1 106.84(13) . . ? C14 N6 C10 124.0(2) . . ? C14 N6 H6A 119(2) . . ? C10 N6 H6A 117(2) . . ? C3 N3 C2 123.3(2) . . ? C3 N3 H3A 120(2) . . ? C2 N3 H3A 117(2) . . ? C1 N1 N2 111.9(2) . . ? C2 N2 N1 112.4(2) . . ? C12 C11 C10 120.7(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C9 N5 C5 124.0(2) . . ? C9 N5 H5A 118(2) . . ? C5 N5 H5A 118(2) . . ? O4 C5 N5 119.9(2) . . ? O4 C5 C6 124.9(2) . . ? N5 C5 C6 115.3(2) . . ? S2 N4 H4A 116(3) . . ? S2 N4 H4B 109(3) . . ? H4A N4 H4B 119(4) . . ? O5 C10 N6 120.2(2) . . ? O5 C10 C11 124.5(2) . . ? N6 C10 C11 115.3(2) . . ? O1 C3 N3 121.0(3) . . ? O1 C3 C4 123.1(3) . . ? N3 C3 C4 115.9(2) . . ? N2 C2 N3 120.9(2) . . ? N2 C2 S1 114.39(19) . . ? N3 C2 S1 124.73(18) . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? N1 C1 S1 115.6(2) . . ? N1 C1 S2 123.4(2) . . ? S1 C1 S2 120.98(14) . . ? C14 C13 C12 118.3(3) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? N6 C14 C13 120.5(3) . . ? N6 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C9 C8 C7 117.9(3) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? C11 C12 C13 121.1(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C6 C7 C8 121.1(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C3 C4 H4C 109.5 . . ? C3 C4 H4D 109.5 . . ? H4C C4 H4D 109.5 . . ? C3 C4 H4E 109.5 . . ? H4C C4 H4E 109.5 . . ? H4D C4 H4E 109.5 . . ? N5 C9 C8 120.9(3) . . ? N5 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.465 _refine_diff_density_min -0.802 _refine_diff_density_rms 0.182 data_ACZCPRH111 _database_code_depnum_ccdc_archive 'CCDC 1436983' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE; CAPROLACTAM; HYDRATE' _chemical_melting_point 353 _chemical_formula_moiety 'C4H6N4O3S2,C6H11NO,H2O' _chemical_formula_sum 'C10 H19 N5 O5 S2' _chemical_formula_weight 353.42 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9969(2) _cell_length_b 11.6983(6) _cell_length_c 14.6244(8) _cell_angle_alpha 70.868(5) _cell_angle_beta 81.892(4) _cell_angle_gamma 80.262(4) _cell_volume 792.64(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2588 _cell_measurement_theta_min 4.2750 _cell_measurement_theta_max 71.6100 _exptl_crystal_description Block _exptl_crystal_colour colorles _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 3.340 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.34353 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4238 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 67.07 _reflns_number_total 2792 _reflns_number_gt 2633 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+0.2015P] 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 2792 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.46604(9) 0.66085(4) 0.81893(3) 0.03689(17) Uani 1 1 d . . . S2 S 0.13348(9) 0.88093(4) 0.86580(3) 0.03464(16) Uani 1 1 d . . . N1 N 0.5296(3) 0.72165(15) 0.96732(11) 0.0366(4) Uani 1 1 d . . . O3 O -0.0206(3) 0.85828(14) 0.80014(11) 0.0457(4) Uani 1 1 d . . . O2 O 0.0081(3) 0.89119(14) 0.95736(10) 0.0466(4) Uani 1 1 d . . . N3 N 0.8821(4) 0.48098(15) 0.88493(12) 0.0368(4) Uani 1 1 d . . . N2 N 0.7199(3) 0.62081(14) 0.96965(12) 0.0371(4) Uani 1 1 d . . . N4 N 0.2778(4) 0.99761(15) 0.81091(14) 0.0429(4) Uani 1 1 d . . . O1 O 0.6895(4) 0.47394(14) 0.75737(12) 0.0539(4) Uani 1 1 d . . . C2 C 0.7098(4) 0.58016(16) 0.89711(13) 0.0328(4) Uani 1 1 d . . . C1 C 0.3890(4) 0.75179(16) 0.89379(13) 0.0324(4) Uani 1 1 d . . . C3 C 0.8640(4) 0.43117(17) 0.81336(14) 0.0390(4) Uani 1 1 d . . . C4 C 1.0735(5) 0.3246(2) 0.81105(18) 0.0528(5) Uani 1 1 d . . . H4A H 1.0230 0.2843 0.7697 0.079 Uiso 1 1 calc R . . H4B H 1.0847 0.2685 0.8756 0.079 Uiso 1 1 calc R . . H4C H 1.2474 0.3523 0.7864 0.079 Uiso 1 1 calc R . . O5 O 0.4198(4) 0.88908(18) 0.10029(14) 0.0568(4) Uani 1 1 d . . . O4 O 0.5211(4) 0.97154(16) 0.38384(11) 0.0561(4) Uani 1 1 d . . . N5 N 0.2630(4) 0.88580(17) 0.51860(14) 0.0481(4) Uani 1 1 d . . . C5 C 0.3483(4) 0.90157(19) 0.42601(15) 0.0427(5) Uani 1 1 d . . . C9 C 0.1699(7) 0.6720(3) 0.5939(2) 0.0746(8) Uani 1 1 d . . . H9A H 0.3564 0.6564 0.6108 0.089 Uiso 1 1 calc R . . H9B H 0.0608 0.6243 0.6489 0.089 Uiso 1 1 calc R . . C6 C 0.2383(5) 0.8302(2) 0.37460(17) 0.0534(6) Uani 1 1 d . . . H6A H 0.3010 0.8579 0.3061 0.064 Uiso 1 1 calc R . . H6B H 0.0407 0.8460 0.3805 0.064 Uiso 1 1 calc R . . C7 C 0.3268(6) 0.6928(2) 0.4155(2) 0.0677(7) Uani 1 1 d . . . H7A H 0.3143 0.6554 0.3663 0.081 Uiso 1 1 calc R . . H7B H 0.5166 0.6795 0.4284 0.081 Uiso 1 1 calc R . . C10 C 0.0673(6) 0.8057(2) 0.57692(19) 0.0590(6) Uani 1 1 d . . . H10A H -0.0990 0.8260 0.5446 0.071 Uiso 1 1 calc R . . H10B H 0.0231 0.8202 0.6393 0.071 Uiso 1 1 calc R . . C8 C 0.1611(7) 0.6293(2) 0.5076(3) 0.0772(9) Uani 1 1 d . . . H8A H -0.0274 0.6402 0.4937 0.093 Uiso 1 1 calc R . . H8B H 0.2252 0.5425 0.5255 0.093 Uiso 1 1 calc R . . H4E H 0.367(6) 1.022(3) 0.850(2) 0.058(7) Uiso 1 1 d . . . H3A H 0.998(5) 0.455(2) 0.9228(18) 0.039(6) Uiso 1 1 d . . . H5A H 0.329(6) 0.923(2) 0.5448(19) 0.050(7) Uiso 1 1 d . . . H4D H 0.349(5) 1.006(2) 0.751(2) 0.050(7) Uiso 1 1 d . . . H5B H 0.287(8) 0.934(3) 0.076(2) 0.079(10) Uiso 1 1 d . . . H5C H 0.469(10) 0.853(4) 0.068(3) 0.127(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0384(3) 0.0384(3) 0.0366(3) -0.0158(2) -0.01233(19) 0.00291(19) S2 0.0302(3) 0.0381(3) 0.0352(3) -0.01345(19) -0.00382(18) 0.00124(18) N1 0.0373(8) 0.0387(8) 0.0349(8) -0.0136(7) -0.0063(6) -0.0013(6) O3 0.0389(8) 0.0512(8) 0.0501(8) -0.0186(7) -0.0124(6) -0.0014(6) O2 0.0409(8) 0.0547(8) 0.0426(8) -0.0197(7) 0.0022(6) 0.0022(6) N3 0.0365(9) 0.0349(8) 0.0396(9) -0.0123(7) -0.0127(7) 0.0027(6) N2 0.0387(9) 0.0371(8) 0.0362(8) -0.0127(6) -0.0093(6) 0.0006(6) N4 0.0493(10) 0.0381(9) 0.0410(10) -0.0122(7) -0.0069(8) -0.0035(7) O1 0.0611(10) 0.0526(9) 0.0560(9) -0.0277(7) -0.0247(8) 0.0082(7) C2 0.0309(9) 0.0341(9) 0.0326(9) -0.0078(7) -0.0062(7) -0.0045(7) C1 0.0309(9) 0.0325(9) 0.0340(9) -0.0119(7) -0.0029(7) -0.0018(7) C3 0.0416(11) 0.0344(9) 0.0409(10) -0.0114(8) -0.0059(8) -0.0035(8) C4 0.0578(14) 0.0464(12) 0.0569(13) -0.0245(10) -0.0091(11) 0.0064(10) O5 0.0546(11) 0.0621(10) 0.0618(11) -0.0334(9) -0.0177(8) 0.0095(8) O4 0.0656(11) 0.0634(10) 0.0453(8) -0.0186(7) 0.0041(7) -0.0290(8) N5 0.0575(12) 0.0494(10) 0.0454(10) -0.0212(8) 0.0012(8) -0.0205(9) C5 0.0447(11) 0.0414(10) 0.0435(11) -0.0141(8) -0.0062(9) -0.0061(8) C9 0.094(2) 0.0565(15) 0.0684(17) 0.0009(13) -0.0192(16) -0.0294(15) C6 0.0556(14) 0.0651(14) 0.0475(12) -0.0221(11) -0.0106(10) -0.0154(11) C7 0.0662(16) 0.0645(16) 0.093(2) -0.0497(15) -0.0225(15) -0.0017(13) C10 0.0631(15) 0.0655(15) 0.0523(13) -0.0202(11) 0.0078(11) -0.0263(12) C8 0.085(2) 0.0432(13) 0.111(2) -0.0211(14) -0.0362(18) -0.0118(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 S1 C2 1.7259(18) . ? S1 C1 1.7276(18) . ? S2 O3 1.4247(15) . ? S2 O2 1.4295(15) . ? S2 N4 1.5745(18) . ? S2 C1 1.7804(18) . ? N1 C1 1.287(2) . ? N1 N2 1.378(2) . ? N3 C2 1.369(3) . ? N3 C3 1.374(3) . ? N2 C2 1.307(2) . ? O1 C3 1.211(3) . ? C3 C4 1.493(3) . ? O4 C5 1.247(3) . ? N5 C5 1.323(3) . ? N5 C10 1.453(3) . ? C5 C6 1.499(3) . ? C9 C8 1.510(4) . ? C9 C10 1.511(4) . ? C6 C7 1.530(4) . ? C7 C8 1.513(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C1 85.27(9) . . ? O3 S2 O2 120.63(9) . . ? O3 S2 N4 108.90(10) . . ? O2 S2 N4 108.60(10) . . ? O3 S2 C1 104.01(9) . . ? O2 S2 C1 105.71(9) . . ? N4 S2 C1 108.33(9) . . ? C1 N1 N2 111.55(15) . . ? C2 N3 C3 123.01(17) . . ? C2 N2 N1 111.94(15) . . ? N2 C2 N3 121.76(17) . . ? N2 C2 S1 115.08(14) . . ? N3 C2 S1 123.16(14) . . ? N1 C1 S1 116.16(14) . . ? N1 C1 S2 123.64(14) . . ? S1 C1 S2 120.19(11) . . ? O1 C3 N3 120.60(19) . . ? O1 C3 C4 124.51(19) . . ? N3 C3 C4 114.88(18) . . ? C5 N5 C10 126.3(2) . . ? O4 C5 N5 120.5(2) . . ? O4 C5 C6 121.2(2) . . ? N5 C5 C6 118.22(19) . . ? C8 C9 C10 114.0(2) . . ? C5 C6 C7 112.5(2) . . ? C8 C7 C6 114.5(2) . . ? N5 C10 C9 113.3(2) . . ? C9 C8 C7 115.7(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 67.07 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.244 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.059 data_ACZDMSO _database_code_depnum_ccdc_archive 'CCDC 1451431' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE;DMSO' _chemical_melting_point 423 _chemical_formula_moiety '2(C4H6N4O3S2),C2H6OS' _chemical_formula_sum 'C10 H18 N8 O7 S5' _chemical_formula_weight 522.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'C2/c' 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' '-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 52.62(3) _cell_length_b 4.816(2) _cell_length_c 17.814(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.785(13) _cell_angle_gamma 90.00 _cell_volume 4322(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8298 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.67 _exptl_crystal_description Plate _exptl_crystal_colour colorles _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 0.587 _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 298(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 21342 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -64 _diffrn_reflns_limit_h_max 64 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.45 _reflns_number_total 4378 _reflns_number_gt 3834 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+4.6734P] 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 4378 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.002 _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 S3 S 0.006883(10) -0.05456(11) 0.15916(3) 0.03631(14) Uani 1 1 d . . . S4 S 0.063213(11) -0.27631(11) 0.21613(3) 0.03644(14) Uani 1 1 d . . . O4 O -0.04452(3) 0.0799(3) 0.12430(9) 0.0474(4) Uani 1 1 d . . . N7 N -0.02235(3) 0.3259(4) 0.05622(10) 0.0355(4) Uani 1 1 d . . . O6 O 0.04826(3) -0.4541(3) 0.25137(10) 0.0513(4) Uani 1 1 d . . . C6 C 0.00128(4) 0.1927(4) 0.08639(11) 0.0317(4) Uani 1 1 d . . . N5 N 0.04358(3) 0.0927(4) 0.09867(10) 0.0369(4) Uani 1 1 d . . . N8 N 0.08079(4) -0.0763(4) 0.28187(12) 0.0416(4) Uani 1 1 d . . . O5 O 0.07982(3) -0.3869(4) 0.17311(10) 0.0516(4) Uani 1 1 d . . . N6 N 0.02160(3) 0.2467(4) 0.06040(10) 0.0374(4) Uani 1 1 d . . . C7 C -0.04479(4) 0.2645(5) 0.07735(12) 0.0368(5) Uani 1 1 d . . . C5 C 0.03872(4) -0.0674(4) 0.15096(11) 0.0328(4) Uani 1 1 d . . . C8 C -0.06839(5) 0.4366(6) 0.03851(15) 0.0510(6) Uani 1 1 d . . . H8A H -0.0841 0.3476 0.0437 0.077 Uiso 1 1 calc R . . H8B H -0.0697 0.4570 -0.0161 0.077 Uiso 1 1 calc R . . H8C H -0.0666 0.6163 0.0628 0.077 Uiso 1 1 calc R . . S2 S 0.145927(11) 0.33975(11) 0.45615(3) 0.03771(14) Uani 1 1 d . . . S1 S 0.193875(12) 0.26355(14) 0.39428(4) 0.04959(17) Uani 1 1 d . . . N4 N 0.12674(4) 0.4870(5) 0.38253(13) 0.0435(5) Uani 1 1 d . . . O3 O 0.14239(4) 0.4519(4) 0.52612(9) 0.0549(4) Uani 1 1 d . . . N2 N 0.21778(4) 0.6305(5) 0.49380(12) 0.0495(5) Uani 1 1 d . . . C2 C 0.22078(4) 0.4699(5) 0.43775(13) 0.0423(5) Uani 1 1 d . . . C1 C 0.17893(4) 0.4219(5) 0.45742(12) 0.0383(5) Uani 1 1 d . . . N1 N 0.19316(4) 0.6020(4) 0.50505(12) 0.0467(5) Uani 1 1 d . . . O2 O 0.14364(4) 0.0484(3) 0.44237(11) 0.0542(4) Uani 1 1 d . . . N3 N 0.24391(4) 0.4683(5) 0.41755(13) 0.0484(5) Uani 1 1 d . . . C3 C 0.24843(5) 0.3005(6) 0.36117(15) 0.0576(7) Uani 1 1 d . . . O1 O 0.23177(4) 0.1342(6) 0.32735(14) 0.0918(8) Uani 1 1 d . . . C4 C 0.27461(6) 0.3372(8) 0.34596(17) 0.0676(8) Uani 1 1 d . . . H4A H 0.2827 0.1589 0.3449 0.101 Uiso 1 1 calc R . . H4B H 0.2859 0.4485 0.3868 0.101 Uiso 1 1 calc R . . H4C H 0.2721 0.4279 0.2964 0.101 Uiso 1 1 calc R . . S5 S 0.134755(13) 0.27251(13) 0.18180(4) 0.04840(17) Uani 1 1 d . . . O7 O 0.13023(4) 0.1643(4) 0.25691(9) 0.0564(5) Uani 1 1 d . . . C9 C 0.11184(5) 0.0939(6) 0.10491(13) 0.0504(6) Uani 1 1 d . . . H9A H 0.1137 -0.1024 0.1142 0.076 Uiso 1 1 calc R . . H9B H 0.1152 0.1371 0.0561 0.076 Uiso 1 1 calc R . . H9C H 0.0941 0.1500 0.1026 0.076 Uiso 1 1 calc R . . C10 C 0.16389(5) 0.1016(8) 0.17402(17) 0.0722(9) Uani 1 1 d . . . H10A H 0.1790 0.1680 0.2144 0.108 Uiso 1 1 calc R . . H10B H 0.1663 0.1397 0.1236 0.108 Uiso 1 1 calc R . . H10C H 0.1621 -0.0949 0.1799 0.108 Uiso 1 1 calc R . . H4D H 0.1278(5) 0.415(6) 0.3405(17) 0.056(8) Uiso 1 1 d . . . H7A H -0.0230(4) 0.441(5) 0.0219(12) 0.029(6) Uiso 1 1 d . . . H4E H 0.1260(5) 0.634(6) 0.3891(15) 0.039(8) Uiso 1 1 d . . . H8D H 0.0928(6) 0.013(6) 0.2678(15) 0.052(8) Uiso 1 1 d . . . H8E H 0.0721(6) -0.010(6) 0.3084(16) 0.060(9) Uiso 1 1 d . . . H3A H 0.2545(5) 0.567(6) 0.4397(15) 0.050(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S3 0.0381(3) 0.0379(3) 0.0362(3) 0.0080(2) 0.0160(2) 0.0009(2) S4 0.0398(3) 0.0301(3) 0.0407(3) 0.0033(2) 0.0136(2) 0.0057(2) O4 0.0456(9) 0.0491(10) 0.0541(9) 0.0120(8) 0.0249(7) -0.0005(7) N7 0.0342(9) 0.0389(10) 0.0337(9) 0.0089(8) 0.0104(7) -0.0011(7) O6 0.0545(10) 0.0421(9) 0.0588(10) 0.0157(8) 0.0189(8) 0.0005(8) C6 0.0350(10) 0.0327(10) 0.0280(9) -0.0006(8) 0.0098(8) -0.0048(8) N5 0.0348(9) 0.0411(10) 0.0358(9) 0.0044(8) 0.0116(7) 0.0002(8) N8 0.0397(10) 0.0453(11) 0.0394(10) 0.0006(9) 0.0109(8) 0.0043(9) O5 0.0557(10) 0.0444(9) 0.0600(10) -0.0057(8) 0.0250(8) 0.0119(8) N6 0.0340(9) 0.0435(10) 0.0350(9) 0.0083(7) 0.0105(7) -0.0016(7) C7 0.0348(11) 0.0405(12) 0.0359(11) -0.0025(9) 0.0114(9) -0.0037(9) C5 0.0356(10) 0.0325(10) 0.0309(10) -0.0007(8) 0.0106(8) 0.0010(8) C8 0.0364(12) 0.0612(16) 0.0547(14) 0.0067(12) 0.0119(10) 0.0043(11) S2 0.0394(3) 0.0343(3) 0.0405(3) -0.0010(2) 0.0131(2) -0.0055(2) S1 0.0421(3) 0.0571(4) 0.0507(4) -0.0174(3) 0.0152(3) -0.0143(3) N4 0.0423(11) 0.0383(12) 0.0485(13) -0.0056(10) 0.0109(9) 0.0014(9) O3 0.0643(11) 0.0617(11) 0.0448(9) -0.0059(8) 0.0254(8) -0.0113(9) N2 0.0350(10) 0.0523(12) 0.0563(12) -0.0129(10) 0.0055(9) -0.0047(9) C2 0.0349(11) 0.0426(12) 0.0443(12) -0.0007(10) 0.0034(9) -0.0049(9) C1 0.0362(11) 0.0378(12) 0.0386(11) -0.0003(9) 0.0071(9) -0.0016(9) N1 0.0347(10) 0.0490(12) 0.0515(11) -0.0095(9) 0.0047(8) -0.0018(8) O2 0.0596(10) 0.0334(9) 0.0693(11) 0.0019(8) 0.0184(9) -0.0064(8) N3 0.0354(10) 0.0558(13) 0.0515(12) -0.0068(10) 0.0085(9) -0.0096(9) C3 0.0494(15) 0.0767(19) 0.0479(14) -0.0072(13) 0.0157(12) -0.0093(13) O1 0.0690(14) 0.130(2) 0.0859(15) -0.0586(16) 0.0367(12) -0.0363(14) C4 0.0557(16) 0.098(2) 0.0542(16) 0.0036(16) 0.0240(13) -0.0054(16) S5 0.0511(4) 0.0509(4) 0.0475(3) -0.0054(3) 0.0210(3) -0.0027(3) O7 0.0606(11) 0.0700(12) 0.0417(9) -0.0046(8) 0.0195(8) -0.0001(9) C9 0.0455(13) 0.0634(16) 0.0425(13) 0.0031(11) 0.0131(10) 0.0000(12) C10 0.0413(14) 0.118(3) 0.0572(16) -0.0061(17) 0.0136(12) 0.0113(16) _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 S3 C6 1.722(2) . ? S3 C5 1.724(2) . ? S4 O5 1.4217(17) . ? S4 O6 1.4252(17) . ? S4 N8 1.590(2) . ? S4 C5 1.777(2) . ? O4 C7 1.218(3) . ? N7 C6 1.364(3) . ? N7 C7 1.371(3) . ? C6 N6 1.308(3) . ? N5 C5 1.290(3) . ? N5 N6 1.378(2) . ? C7 C8 1.487(3) . ? S2 O3 1.4192(18) . ? S2 O2 1.4235(19) . ? S2 N4 1.574(2) . ? S2 C1 1.775(2) . ? S1 C2 1.720(2) . ? S1 C1 1.725(2) . ? N2 C2 1.308(3) . ? N2 N1 1.374(3) . ? C2 N3 1.365(3) . ? C1 N1 1.291(3) . ? N3 C3 1.363(3) . ? C3 O1 1.211(3) . ? C3 C4 1.489(4) . ? S5 O7 1.5172(19) . ? S5 C9 1.765(3) . ? S5 C10 1.780(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S3 C5 85.43(10) . . ? O5 S4 O6 121.06(11) . . ? O5 S4 N8 107.84(12) . . ? O6 S4 N8 108.49(12) . . ? O5 S4 C5 107.61(10) . . ? O6 S4 C5 103.86(10) . . ? N8 S4 C5 107.22(11) . . ? C6 N7 C7 123.36(19) . . ? N6 C6 N7 120.83(18) . . ? N6 C6 S3 115.10(16) . . ? N7 C6 S3 124.07(15) . . ? C5 N5 N6 111.46(17) . . ? C6 N6 N5 111.91(17) . . ? O4 C7 N7 120.4(2) . . ? O4 C7 C8 124.7(2) . . ? N7 C7 C8 114.93(19) . . ? N5 C5 S3 116.08(15) . . ? N5 C5 S4 123.54(16) . . ? S3 C5 S4 120.27(12) . . ? O3 S2 O2 120.03(11) . . ? O3 S2 N4 110.19(13) . . ? O2 S2 N4 107.36(12) . . ? O3 S2 C1 106.27(11) . . ? O2 S2 C1 104.81(11) . . ? N4 S2 C1 107.46(11) . . ? C2 S1 C1 85.53(11) . . ? C2 N2 N1 112.29(19) . . ? N2 C2 N3 121.2(2) . . ? N2 C2 S1 114.83(18) . . ? N3 C2 S1 123.97(19) . . ? N1 C1 S1 116.01(17) . . ? N1 C1 S2 122.54(18) . . ? S1 C1 S2 121.45(13) . . ? C1 N1 N2 111.32(19) . . ? C3 N3 C2 123.8(2) . . ? O1 C3 N3 120.2(3) . . ? O1 C3 C4 124.2(3) . . ? N3 C3 C4 115.5(2) . . ? O7 S5 C9 105.72(12) . . ? O7 S5 C10 105.53(13) . . ? C9 S5 C10 97.18(14) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.425 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.059 data_ACZMeHP11 _database_code_depnum_ccdc_archive 'CCDC 1436982' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE;6 Me 2 PYRIDONE' _chemical_melting_point 403 _chemical_formula_moiety C4H6N4O3S2,C6H7NO _chemical_formula_sum 'C10 H13 N5 O4 S2' _chemical_formula_weight 331.37 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p_1_c_1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.3972(7) _cell_length_b 18.1641(3) _cell_length_c 10.338(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.046(16) _cell_angle_gamma 90.00 _cell_volume 2124.0(6) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3599 _cell_measurement_theta_min 4.6010 _cell_measurement_theta_max 71.4380 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLES _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 3.652 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.73197 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7371 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 67.07 _reflns_number_total 4590 _reflns_number_gt 4295 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.19(2) _refine_ls_number_reflns 4590 _refine_ls_number_parameters 583 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.026 _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 S4 S 0.28049(9) 0.44599(6) -0.01359(11) 0.0376(3) Uani 1 1 d . . . S3 S 0.30014(9) 0.27942(6) 0.02210(11) 0.0382(3) Uani 1 1 d . . . O4 O 0.2805(3) 0.13407(19) 0.0506(4) 0.0573(10) Uani 1 1 d . . . O6 O 0.1619(3) 0.4225(2) -0.0057(4) 0.0549(9) Uani 1 1 d . . . O5 O 0.3345(3) 0.50038(19) 0.0722(4) 0.0590(9) Uani 1 1 d . . . N5 N 0.4796(3) 0.3647(2) 0.0308(4) 0.0409(9) Uani 1 1 d . . . N6 N 0.5258(3) 0.2955(2) 0.0511(4) 0.0411(8) Uani 1 1 d . . . N7 N 0.4699(3) 0.1731(2) 0.0715(4) 0.0449(9) Uani 1 1 d . . . H41 H 0.5431 0.1606 0.0858 0.054 Uiso 1 1 d R . . N8 N 0.2915(3) 0.4716(2) -0.1575(4) 0.0424(8) Uani 1 1 d . . . H6A H 0.3718 0.4911 -0.1596 0.051 Uiso 1 1 d R . . H6B H 0.2570 0.4484 -0.2139 0.051 Uiso 1 1 d R . . C8 C 0.4348(6) 0.0452(3) 0.0997(8) 0.0729(19) Uani 1 1 d . . . H8A H 0.4006 0.0246 0.1720 0.109 Uiso 1 1 calc R . . H8B H 0.5191 0.0484 0.1212 0.109 Uiso 1 1 calc R . . H8C H 0.4167 0.0143 0.0246 0.109 Uiso 1 1 calc R . . C6 C 0.4428(3) 0.2445(3) 0.0508(4) 0.0350(9) Uani 1 1 d . . . C7 C 0.3858(4) 0.1197(3) 0.0710(5) 0.0488(12) Uani 1 1 d . . . C5 C 0.3653(4) 0.3649(2) 0.0142(4) 0.0335(9) Uani 1 1 d . . . S5 S 0.10227(8) 0.22150(6) 0.72588(10) 0.0358(2) Uani 1 1 d . . . S6 S 0.12122(10) 0.05538(6) 0.75917(11) 0.0400(3) Uani 1 1 d . . . O7 O 0.1220(3) 0.36760(19) 0.6924(4) 0.0535(9) Uani 1 1 d . . . O9 O 0.0660(4) 0.00099(19) 0.6728(4) 0.0605(10) Uani 1 1 d . . . O8 O 0.2374(3) 0.0809(2) 0.7441(4) 0.0630(11) Uani 1 1 d . . . N9 N -0.0787(4) 0.1382(2) 0.7396(4) 0.0446(10) Uani 1 1 d . . . N11 N -0.0653(3) 0.3308(2) 0.7024(4) 0.0396(8) Uani 1 1 d . . . H11A H -0.1380 0.3441 0.7005 0.047 Uiso 1 1 d R . . N12 N 0.1148(4) 0.0280(2) 0.9023(4) 0.0497(10) Uani 1 1 d D . . H12D H 0.0681 -0.0158 0.9096 0.060 Uiso 1 1 d R . . H12E H 0.1412 0.0525 0.9528 0.060 Uiso 1 1 d RD . . N10 N -0.1225(3) 0.2087(2) 0.7257(4) 0.0436(9) Uani 1 1 d . . . C10 C -0.0376(4) 0.2574(2) 0.7178(4) 0.0344(9) Uani 1 1 d . . . C12 C -0.0299(5) 0.4598(3) 0.6730(7) 0.0649(17) Uani 1 1 d . . . H12A H -0.0753 0.4713 0.7427 0.097 Uiso 1 1 calc R . . H12B H -0.0796 0.4632 0.5912 0.097 Uiso 1 1 calc R . . H12C H 0.0344 0.4940 0.6738 0.097 Uiso 1 1 calc R . . C11 C 0.0178(4) 0.3835(3) 0.6906(5) 0.0431(11) Uani 1 1 d . . . C9 C 0.0359(4) 0.1375(2) 0.7408(4) 0.0347(9) Uani 1 1 d . . . S1 S 0.63545(9) 0.27176(6) 0.37991(11) 0.0397(3) Uani 1 1 d . . . S2 S 0.61804(10) 0.43922(6) 0.34541(11) 0.0385(2) Uani 1 1 d . . . O3 O 0.4989(3) 0.41432(19) 0.3455(4) 0.0573(9) Uani 1 1 d . . . O1 O 0.6167(3) 0.1249(2) 0.4129(5) 0.0682(12) Uani 1 1 d . . . O2 O 0.6675(4) 0.48895(19) 0.4430(4) 0.0617(10) Uani 1 1 d . . . N1 N 0.8152(3) 0.3555(2) 0.3680(4) 0.0420(9) Uani 1 1 d . . . N2 N 0.8596(3) 0.2849(2) 0.3864(4) 0.0418(8) Uani 1 1 d . . . N4 N 0.6389(4) 0.4712(2) 0.2079(4) 0.0446(9) Uani 1 1 d D . . H4D H 0.5983 0.4581 0.1403 0.054 Uiso 1 1 d R . . N3 N 0.8042(3) 0.1637(2) 0.4104(4) 0.0394(8) Uani 1 1 d . . . C2 C 0.7768(4) 0.2354(2) 0.3929(4) 0.0309(9) Uani 1 1 d . . . C4 C 0.7705(6) 0.0349(3) 0.4338(8) 0.080(2) Uani 1 1 d . . . H4A H 0.7213 0.0056 0.4826 0.119 Uiso 1 1 calc R . . H4B H 0.8491 0.0369 0.4793 0.119 Uiso 1 1 calc R . . H4C H 0.7727 0.0133 0.3494 0.119 Uiso 1 1 calc R . . C3 C 0.7218(4) 0.1102(3) 0.4186(6) 0.0511(12) Uani 1 1 d . . . C1 C 0.7018(4) 0.3562(2) 0.3629(4) 0.0353(9) Uani 1 1 d . . . O12 O 0.7022(3) 0.37071(18) 0.6965(4) 0.0497(8) Uani 1 1 d . . . N14 N 0.6329(3) 0.2555(2) 0.7260(4) 0.0393(8) Uani 1 1 d . . . H8 H 0.7047 0.2402 0.7387 0.047 Uiso 1 1 d R . . C20 C 0.4947(4) 0.3514(3) 0.6817(5) 0.0454(11) Uani 1 1 d . . . H20 H 0.4757 0.4006 0.6650 0.054 Uiso 1 1 calc R . . C19 C 0.6146(4) 0.3287(2) 0.7012(4) 0.0378(9) Uani 1 1 d . . . C22 C 0.4318(5) 0.2274(3) 0.7137(5) 0.0492(12) Uani 1 1 d . . . H22 H 0.3706 0.1940 0.7185 0.059 Uiso 1 1 calc R . . C21 C 0.4078(4) 0.3010(3) 0.6876(5) 0.0502(12) Uani 1 1 d . . . H21 H 0.3294 0.3163 0.6737 0.060 Uiso 1 1 calc R . . C24 C 0.5861(6) 0.1268(3) 0.7586(6) 0.0631(15) Uani 1 1 d . . . H24A H 0.5198 0.0971 0.7749 0.095 Uiso 1 1 calc R . . H24B H 0.6449 0.1256 0.8335 0.095 Uiso 1 1 calc R . . H24C H 0.6192 0.1078 0.6843 0.095 Uiso 1 1 calc R . . C23 C 0.5461(4) 0.2048(3) 0.7322(5) 0.0430(11) Uani 1 1 d . . . O11 O 0.0398(3) 0.12277(16) 0.4260(3) 0.0455(7) Uani 1 1 d . . . N15 N 0.1045(3) 0.2370(2) 0.3838(4) 0.0389(9) Uani 1 1 d . . . H18 H 0.0326 0.2519 0.3805 0.047 Uiso 1 1 d R . . C28 C 0.3019(5) 0.2660(3) 0.3663(6) 0.0554(14) Uani 1 1 d . . . H28 H 0.3608 0.2995 0.3526 0.067 Uiso 1 1 calc R . . C30 C 0.1456(6) 0.3648(3) 0.3433(7) 0.0648(16) Uani 1 1 d . . . H30A H 0.1424 0.3882 0.4261 0.097 Uiso 1 1 calc R . . H30B H 0.0680 0.3644 0.2951 0.097 Uiso 1 1 calc R . . H30C H 0.1986 0.3915 0.2952 0.097 Uiso 1 1 calc R . . C25 C 0.1252(4) 0.1634(2) 0.4082(4) 0.0391(9) Uani 1 1 d . . . C29 C 0.1883(4) 0.2883(3) 0.3641(5) 0.0458(11) Uani 1 1 d . . . C26 C 0.2446(5) 0.1411(3) 0.4093(6) 0.0521(13) Uani 1 1 d . . . H26 H 0.2650 0.0919 0.4235 0.063 Uiso 1 1 calc R . . C27 C 0.3292(4) 0.1909(3) 0.3897(5) 0.0597(14) Uani 1 1 d . . . H27 H 0.4072 0.1753 0.3918 0.072 Uiso 1 1 calc R . . O10 O 0.6983(3) 0.86477(19) 0.6009(4) 0.0580(9) Uani 1 1 d . . . N13 N 0.7772(3) 0.7540(2) 0.5595(4) 0.0402(8) Uani 1 1 d . . . H13A H 0.7070 0.7359 0.5512 0.048 Uiso 1 1 d R . . C16 C 0.9796(4) 0.7358(3) 0.5538(5) 0.0500(12) Uani 1 1 d . . . H16 H 1.0436 0.7058 0.5424 0.060 Uiso 1 1 calc R . . C13 C 0.7879(4) 0.8275(3) 0.5867(5) 0.0436(10) Uani 1 1 d . . . C14 C 0.9056(5) 0.8560(3) 0.5969(5) 0.0515(13) Uani 1 1 d . . . H14 H 0.9192 0.9057 0.6142 0.062 Uiso 1 1 calc R . . C18 C 0.8373(5) 0.6291(3) 0.5169(6) 0.0533(12) Uani 1 1 d . . . H18A H 0.9042 0.6039 0.4898 0.080 Uiso 1 1 calc R . . H18B H 0.7720 0.6263 0.4489 0.080 Uiso 1 1 calc R . . H18C H 0.8157 0.6065 0.5945 0.080 Uiso 1 1 calc R . . C17 C 0.8680(4) 0.7066(3) 0.5436(5) 0.0434(10) Uani 1 1 d . . . C15 C 0.9974(4) 0.8109(3) 0.5814(5) 0.0549(13) Uani 1 1 d . . . H15 H 1.0737 0.8300 0.5893 0.066 Uiso 1 1 calc R . . H4E H 0.656(5) 0.5161(13) 0.204(5) 0.063(16) Uiso 1 1 d D . . H53A H 0.875(4) 0.155(3) 0.423(5) 0.048(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S4 0.0373(5) 0.0325(5) 0.0446(6) 0.0000(4) 0.0116(4) 0.0043(4) S3 0.0266(5) 0.0347(5) 0.0532(6) 0.0010(5) 0.0046(4) -0.0019(4) O4 0.0358(19) 0.042(2) 0.092(3) -0.0007(19) 0.0000(17) -0.0081(14) O6 0.0408(17) 0.054(2) 0.074(2) 0.0140(18) 0.0234(16) 0.0074(15) O5 0.075(2) 0.0427(19) 0.059(2) -0.0133(17) 0.0064(18) 0.0038(17) N5 0.0361(19) 0.031(2) 0.055(2) 0.0009(16) 0.0023(16) -0.0055(14) N6 0.0303(17) 0.0358(19) 0.056(2) 0.0000(16) 0.0005(15) -0.0024(14) N7 0.0289(17) 0.035(2) 0.069(3) 0.0047(18) 0.0018(16) -0.0006(14) N8 0.0440(19) 0.0385(19) 0.044(2) 0.0018(16) 0.0040(16) 0.0000(16) C8 0.057(3) 0.037(3) 0.122(6) 0.012(3) 0.002(3) -0.002(2) C6 0.0224(19) 0.046(3) 0.036(2) -0.0080(19) 0.0010(15) -0.0001(18) C7 0.043(3) 0.038(2) 0.065(3) 0.006(2) 0.007(2) -0.006(2) C5 0.030(2) 0.034(2) 0.036(2) 0.0020(17) 0.0018(16) -0.0008(16) S5 0.0318(5) 0.0285(5) 0.0478(6) -0.0019(4) 0.0078(4) -0.0017(4) S6 0.0446(6) 0.0259(5) 0.0518(7) -0.0006(4) 0.0144(5) 0.0001(4) O7 0.0367(19) 0.0381(19) 0.086(3) 0.0014(17) 0.0102(17) -0.0040(14) O9 0.092(3) 0.0371(18) 0.054(2) -0.0094(16) 0.0126(19) -0.0016(18) O8 0.0479(19) 0.042(2) 0.105(3) 0.010(2) 0.034(2) 0.0074(15) N9 0.038(2) 0.035(2) 0.062(3) 0.0023(17) 0.0093(18) -0.0059(15) N11 0.0310(18) 0.0321(19) 0.055(2) 0.0029(16) 0.0045(16) 0.0022(15) N12 0.065(3) 0.0335(19) 0.050(2) 0.0047(18) 0.0066(19) -0.0082(19) N10 0.0339(19) 0.0344(19) 0.062(3) 0.0040(17) 0.0051(17) -0.0035(16) C10 0.032(2) 0.032(2) 0.038(2) -0.0012(18) 0.0008(17) -0.0014(18) C12 0.050(3) 0.039(3) 0.107(5) 0.013(3) 0.015(3) 0.002(2) C11 0.040(3) 0.035(2) 0.053(3) 0.000(2) 0.001(2) -0.0039(19) C9 0.035(2) 0.026(2) 0.044(2) -0.0001(17) 0.0049(18) -0.0026(16) S1 0.0337(5) 0.0321(5) 0.0541(7) 0.0012(5) 0.0081(5) 0.0011(4) S2 0.0454(6) 0.0291(5) 0.0428(6) 0.0003(4) 0.0128(4) 0.0050(4) O3 0.0479(19) 0.0468(19) 0.083(3) 0.0156(18) 0.0301(17) 0.0108(15) O1 0.040(2) 0.050(2) 0.117(4) 0.008(2) 0.018(2) -0.0044(16) O2 0.092(3) 0.0418(18) 0.051(2) -0.0111(15) 0.0070(18) 0.0106(18) N1 0.041(2) 0.0315(19) 0.055(2) 0.0015(16) 0.0085(16) 0.0009(14) N2 0.0341(17) 0.0330(18) 0.058(2) 0.0040(17) 0.0047(16) 0.0013(15) N4 0.058(2) 0.0321(19) 0.043(2) 0.0032(16) 0.0035(17) -0.0051(17) N3 0.0329(19) 0.0300(18) 0.055(2) 0.0030(16) 0.0048(15) 0.0013(15) C2 0.031(2) 0.031(2) 0.032(2) 0.0037(16) 0.0071(16) 0.0027(16) C4 0.056(3) 0.034(3) 0.148(7) 0.000(4) 0.010(4) 0.002(3) C3 0.046(3) 0.034(2) 0.075(4) 0.002(2) 0.013(2) -0.001(2) C1 0.039(2) 0.031(2) 0.037(2) -0.0007(17) 0.0046(17) 0.0026(17) O12 0.0361(16) 0.0369(17) 0.076(2) 0.0028(15) 0.0081(15) -0.0010(13) N14 0.0323(17) 0.0343(19) 0.051(2) 0.0038(17) 0.0045(15) 0.0030(15) C20 0.037(2) 0.042(2) 0.056(3) -0.001(2) 0.002(2) 0.0099(19) C19 0.034(2) 0.034(2) 0.045(2) -0.0029(18) 0.0058(17) -0.0009(17) C22 0.039(3) 0.057(3) 0.053(3) -0.007(2) 0.009(2) -0.013(2) C21 0.033(2) 0.058(3) 0.059(3) -0.006(2) 0.0041(19) 0.002(2) C24 0.077(4) 0.039(3) 0.076(4) 0.006(3) 0.020(3) -0.010(3) C23 0.044(2) 0.041(2) 0.046(3) -0.004(2) 0.0126(19) -0.009(2) O11 0.0391(15) 0.0318(14) 0.066(2) 0.0051(14) 0.0090(14) -0.0012(13) N15 0.0346(19) 0.0341(19) 0.047(2) 0.0007(16) 0.0035(16) -0.0055(15) C28 0.050(3) 0.057(3) 0.060(3) -0.002(3) 0.010(2) -0.018(2) C30 0.076(4) 0.040(3) 0.079(4) 0.007(3) 0.010(3) -0.012(3) C25 0.039(2) 0.034(2) 0.044(2) -0.0021(18) 0.0058(18) -0.0032(18) C29 0.054(3) 0.040(2) 0.042(2) 0.0014(19) 0.002(2) -0.013(2) C26 0.044(3) 0.039(3) 0.072(4) -0.003(2) 0.004(2) -0.001(2) C27 0.035(2) 0.072(4) 0.073(4) -0.003(3) 0.008(2) -0.007(2) O10 0.0357(16) 0.0432(19) 0.094(3) -0.0068(17) 0.0013(16) -0.0010(13) N13 0.0284(17) 0.044(2) 0.047(2) 0.0029(17) 0.0031(14) -0.0040(15) C16 0.033(2) 0.058(3) 0.059(3) 0.009(2) 0.010(2) 0.000(2) C13 0.035(2) 0.044(2) 0.050(3) 0.0042(19) 0.0002(18) -0.0046(19) C14 0.043(3) 0.045(3) 0.064(3) 0.007(2) 0.001(2) -0.015(2) C18 0.052(3) 0.044(3) 0.064(3) 0.000(2) 0.011(2) 0.000(2) C17 0.039(2) 0.048(3) 0.044(2) 0.007(2) 0.0090(18) 0.0016(19) C15 0.033(2) 0.068(3) 0.064(3) 0.014(3) 0.008(2) -0.009(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 S4 O5 1.417(4) . ? S4 O6 1.429(3) . ? S4 N8 1.579(4) . ? S4 C5 1.767(4) . ? S3 C5 1.727(4) . ? S3 C6 1.736(4) . ? O4 C7 1.222(6) . ? N5 C5 1.293(6) . ? N5 N6 1.370(5) . ? N6 C6 1.324(6) . ? N7 C6 1.344(6) . ? N7 C7 1.364(6) . ? N7 H41 0.8600 . ? N8 H6A 0.9839 . ? N8 H6B 0.7845 . ? C8 C7 1.479(7) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? S5 C10 1.715(5) . ? S5 C9 1.718(4) . ? S6 O9 1.425(4) . ? S6 O8 1.429(4) . ? S6 N12 1.571(4) . ? S6 C9 1.778(4) . ? O7 C11 1.220(6) . ? N9 C9 1.305(6) . ? N9 N10 1.375(5) . ? N11 C11 1.363(6) . ? N11 C10 1.375(6) . ? N11 H11A 0.8600 . ? N12 H12D 0.9651 . ? N12 H12E 0.7225 . ? N10 C10 1.321(6) . ? C12 C11 1.492(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? S1 C1 1.729(4) . ? S1 C2 1.731(4) . ? S2 O2 1.418(4) . ? S2 O3 1.431(3) . ? S2 N4 1.581(4) . ? S2 C1 1.782(4) . ? O1 C3 1.222(6) . ? N1 C1 1.287(6) . ? N1 N2 1.382(5) . ? N2 C2 1.311(6) . ? N4 H4D 0.8244 . ? N4 H4E 0.84(2) . ? N3 C2 1.347(6) . ? N3 C3 1.361(6) . ? N3 H53A 0.82(5) . ? C4 C3 1.477(7) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? O12 C19 1.262(5) . ? N14 C23 1.359(6) . ? N14 C19 1.365(6) . ? N14 H8 0.8598 . ? C20 C21 1.356(7) . ? C20 C19 1.419(6) . ? C20 H20 0.9300 . ? C22 C23 1.356(7) . ? C22 C21 1.385(7) . ? C22 H22 0.9300 . ? C21 H21 0.9300 . ? C24 C23 1.504(7) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? O11 C25 1.253(5) . ? N15 C29 1.367(6) . ? N15 C25 1.376(6) . ? N15 H18 0.8601 . ? C28 C29 1.355(8) . ? C28 C27 1.413(8) . ? C28 H28 0.9300 . ? C30 C29 1.480(7) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C25 C26 1.419(7) . ? C26 C27 1.356(7) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? O10 C13 1.249(5) . ? N13 C13 1.366(6) . ? N13 C17 1.371(6) . ? N13 H13A 0.8600 . ? C16 C17 1.370(7) . ? C16 C15 1.403(8) . ? C16 H16 0.9300 . ? C13 C14 1.430(6) . ? C14 C15 1.354(8) . ? C14 H14 0.9300 . ? C18 C17 1.469(7) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C15 H15 0.9300 . ? 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 O5 S4 O6 120.9(2) . . ? O5 S4 N8 107.8(2) . . ? O6 S4 N8 109.1(2) . . ? O5 S4 C5 107.0(2) . . ? O6 S4 C5 104.1(2) . . ? N8 S4 C5 107.1(2) . . ? C5 S3 C6 86.4(2) . . ? C5 N5 N6 112.6(4) . . ? C6 N6 N5 112.4(4) . . ? C6 N7 C7 122.6(4) . . ? C6 N7 H41 118.7 . . ? C7 N7 H41 118.6 . . ? S4 N8 H6A 107.9 . . ? S4 N8 H6B 116.9 . . ? H6A N8 H6B 124.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N6 C6 N7 121.6(4) . . ? N6 C6 S3 113.5(4) . . ? N7 C6 S3 124.9(3) . . ? O4 C7 N7 121.5(5) . . ? O4 C7 C8 124.7(5) . . ? N7 C7 C8 113.7(5) . . ? N5 C5 S3 115.1(3) . . ? N5 C5 S4 123.0(3) . . ? S3 C5 S4 121.8(2) . . ? C10 S5 C9 85.7(2) . . ? O9 S6 O8 120.0(3) . . ? O9 S6 N12 107.6(2) . . ? O8 S6 N12 110.9(2) . . ? O9 S6 C9 108.7(2) . . ? O8 S6 C9 102.6(2) . . ? N12 S6 C9 106.1(2) . . ? C9 N9 N10 111.1(4) . . ? C11 N11 C10 122.6(4) . . ? C11 N11 H11A 118.7 . . ? C10 N11 H11A 118.7 . . ? S6 N12 H12D 115.1 . . ? S6 N12 H12E 114.9 . . ? H12D N12 H12E 129.5 . . ? C10 N10 N9 111.8(4) . . ? N10 C10 N11 119.8(4) . . ? N10 C10 S5 115.2(3) . . ? N11 C10 S5 125.0(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O7 C11 N11 121.2(4) . . ? O7 C11 C12 124.2(4) . . ? N11 C11 C12 114.6(4) . . ? N9 C9 S5 116.2(3) . . ? N9 C9 S6 122.9(3) . . ? S5 C9 S6 120.9(3) . . ? C1 S1 C2 86.1(2) . . ? O2 S2 O3 119.7(2) . . ? O2 S2 N4 108.4(2) . . ? O3 S2 N4 111.3(2) . . ? O2 S2 C1 107.8(2) . . ? O3 S2 C1 103.2(2) . . ? N4 S2 C1 105.3(2) . . ? C1 N1 N2 111.4(4) . . ? C2 N2 N1 112.9(3) . . ? S2 N4 H4D 121.6 . . ? S2 N4 H4E 117(4) . . ? H4D N4 H4E 110.6 . . ? C2 N3 C3 123.2(4) . . ? C2 N3 H53A 115(4) . . ? C3 N3 H53A 121(4) . . ? N2 C2 N3 120.9(4) . . ? N2 C2 S1 113.8(3) . . ? N3 C2 S1 125.3(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C3 N3 121.4(4) . . ? O1 C3 C4 124.1(5) . . ? N3 C3 C4 114.5(5) . . ? N1 C1 S1 115.8(3) . . ? N1 C1 S2 122.4(3) . . ? S1 C1 S2 121.7(3) . . ? C23 N14 C19 125.0(4) . . ? C23 N14 H8 117.3 . . ? C19 N14 H8 117.6 . . ? C21 C20 C19 119.5(4) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? O12 C19 N14 119.6(4) . . ? O12 C19 C20 124.8(4) . . ? N14 C19 C20 115.6(4) . . ? C23 C22 C21 118.9(5) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C20 C21 C22 122.2(5) . . ? C20 C21 H21 118.9 . . ? C22 C21 H21 118.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C23 N14 118.7(5) . . ? C22 C23 C24 125.1(5) . . ? N14 C23 C24 116.2(4) . . ? C29 N15 C25 125.7(4) . . ? C29 N15 H18 117.3 . . ? C25 N15 H18 117.1 . . ? C29 C28 C27 118.8(5) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O11 C25 N15 118.7(4) . . ? O11 C25 C26 126.3(4) . . ? N15 C25 C26 115.0(4) . . ? C28 C29 N15 118.5(5) . . ? C28 C29 C30 125.4(5) . . ? N15 C29 C30 116.0(5) . . ? C27 C26 C25 120.5(5) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C26 C27 C28 121.6(5) . . ? C26 C27 H27 119.2 . . ? C28 C27 H27 119.2 . . ? C13 N13 C17 126.1(4) . . ? C13 N13 H13A 117.0 . . ? C17 N13 H13A 117.0 . . ? C17 C16 C15 120.1(5) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? O10 C13 N13 120.0(4) . . ? O10 C13 C14 124.6(4) . . ? N13 C13 C14 115.4(4) . . ? C15 C14 C13 120.2(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C17 N13 117.1(5) . . ? C16 C17 C18 125.6(5) . . ? N13 C17 C18 117.3(4) . . ? C14 C15 C16 121.2(4) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N5 N6 C6 -0.8(6) . . . . ? N5 N6 C6 N7 -178.8(4) . . . . ? N5 N6 C6 S3 1.0(5) . . . . ? C7 N7 C6 N6 -179.7(4) . . . . ? C7 N7 C6 S3 0.5(7) . . . . ? C5 S3 C6 N6 -0.8(4) . . . . ? C5 S3 C6 N7 179.0(4) . . . . ? C6 N7 C7 O4 0.5(8) . . . . ? C6 N7 C7 C8 -178.3(5) . . . . ? N6 N5 C5 S3 0.2(5) . . . . ? N6 N5 C5 S4 179.8(3) . . . . ? C6 S3 C5 N5 0.3(4) . . . . ? C6 S3 C5 S4 -179.3(3) . . . . ? O5 S4 C5 N5 -42.1(5) . . . . ? O6 S4 C5 N5 -171.2(4) . . . . ? N8 S4 C5 N5 73.3(4) . . . . ? O5 S4 C5 S3 137.5(3) . . . . ? O6 S4 C5 S3 8.4(3) . . . . ? N8 S4 C5 S3 -107.1(3) . . . . ? C9 N9 N10 C10 -0.2(6) . . . . ? N9 N10 C10 N11 179.4(4) . . . . ? N9 N10 C10 S5 0.2(6) . . . . ? C11 N11 C10 N10 -178.4(4) . . . . ? C11 N11 C10 S5 0.7(7) . . . . ? C9 S5 C10 N10 -0.1(4) . . . . ? C9 S5 C10 N11 -179.3(4) . . . . ? C10 N11 C11 O7 0.4(8) . . . . ? C10 N11 C11 C12 179.2(5) . . . . ? N10 N9 C9 S5 0.1(5) . . . . ? N10 N9 C9 S6 179.3(3) . . . . ? C10 S5 C9 N9 0.0(4) . . . . ? C10 S5 C9 S6 -179.2(3) . . . . ? O9 S6 C9 N9 47.4(5) . . . . ? O8 S6 C9 N9 175.5(4) . . . . ? N12 S6 C9 N9 -68.1(4) . . . . ? O9 S6 C9 S5 -133.5(3) . . . . ? O8 S6 C9 S5 -5.4(4) . . . . ? N12 S6 C9 S5 111.0(3) . . . . ? C1 N1 N2 C2 0.7(6) . . . . ? N1 N2 C2 N3 179.9(4) . . . . ? N1 N2 C2 S1 -1.2(5) . . . . ? C3 N3 C2 N2 179.6(5) . . . . ? C3 N3 C2 S1 0.8(7) . . . . ? C1 S1 C2 N2 1.0(4) . . . . ? C1 S1 C2 N3 179.9(4) . . . . ? C2 N3 C3 O1 -1.5(9) . . . . ? C2 N3 C3 C4 178.2(6) . . . . ? N2 N1 C1 S1 0.1(5) . . . . ? N2 N1 C1 S2 177.8(3) . . . . ? C2 S1 C1 N1 -0.6(4) . . . . ? C2 S1 C1 S2 -178.3(3) . . . . ? O2 S2 C1 N1 -51.9(5) . . . . ? O3 S2 C1 N1 -179.5(4) . . . . ? N4 S2 C1 N1 63.6(4) . . . . ? O2 S2 C1 S1 125.7(3) . . . . ? O3 S2 C1 S1 -1.9(3) . . . . ? N4 S2 C1 S1 -118.8(3) . . . . ? C23 N14 C19 O12 -179.3(4) . . . . ? C23 N14 C19 C20 0.4(7) . . . . ? C21 C20 C19 O12 179.2(5) . . . . ? C21 C20 C19 N14 -0.5(7) . . . . ? C19 C20 C21 C22 0.8(8) . . . . ? C23 C22 C21 C20 -0.9(8) . . . . ? C21 C22 C23 N14 0.8(8) . . . . ? C21 C22 C23 C24 -178.7(5) . . . . ? C19 N14 C23 C22 -0.6(7) . . . . ? C19 N14 C23 C24 179.0(5) . . . . ? C29 N15 C25 O11 179.1(4) . . . . ? C29 N15 C25 C26 -1.5(7) . . . . ? C27 C28 C29 N15 -0.5(8) . . . . ? C27 C28 C29 C30 178.8(5) . . . . ? C25 N15 C29 C28 1.2(8) . . . . ? C25 N15 C29 C30 -178.2(5) . . . . ? O11 C25 C26 C27 -179.4(5) . . . . ? N15 C25 C26 C27 1.3(8) . . . . ? C25 C26 C27 C28 -0.8(9) . . . . ? C29 C28 C27 C26 0.3(9) . . . . ? C17 N13 C13 O10 -178.9(5) . . . . ? C17 N13 C13 C14 1.1(7) . . . . ? O10 C13 C14 C15 179.2(5) . . . . ? N13 C13 C14 C15 -0.8(7) . . . . ? C15 C16 C17 N13 1.0(8) . . . . ? C15 C16 C17 C18 -179.1(5) . . . . ? C13 N13 C17 C16 -1.1(8) . . . . ? C13 N13 C17 C18 178.9(5) . . . . ? C13 C14 C15 C16 0.8(8) . . . . ? C17 C16 C15 C14 -0.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.411 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.061 data_ACZNAM11 _database_code_depnum_ccdc_archive 'CCDC 1436980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE;NICOTINAMIDE' _chemical_melting_point 453 _chemical_formula_moiety 'C4H6N4O3S2,C6H6N2O' _chemical_formula_sum 'C10 H12 N6 O4 S2' _chemical_formula_weight 344.38 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1477(8) _cell_length_b 10.8147(14) _cell_length_c 14.2604(16) _cell_angle_alpha 69.797(11) _cell_angle_beta 85.463(12) _cell_angle_gamma 81.889(12) _cell_volume 737.20(17) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1270 _cell_measurement_theta_min 4.3720 _cell_measurement_theta_max 71.6760 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLES _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 3.554 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method 'multi-scan' _diffrn_detector_area_resol_mean '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4027 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 67.07 _reflns_number_total 2607 _reflns_number_gt 1906 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1157P)^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 2607 _refine_ls_number_parameters 220 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1935 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 S1 S 0.1492(2) 0.93431(10) 0.78260(8) 0.0528(4) Uani 1 1 d . . . S2 S 0.5163(2) 0.78104(10) 0.67044(7) 0.0515(3) Uani 1 1 d . . . N2 N 0.7184(7) 0.9964(3) 0.5809(2) 0.0533(9) Uani 1 1 d . . . N3 N 0.9226(8) 0.8215(4) 0.5326(3) 0.0529(9) Uani 1 1 d . . . N1 N 0.5204(7) 1.0284(3) 0.6423(3) 0.0543(9) Uani 1 1 d . . . O1 O 0.8030(8) 0.6179(3) 0.5851(3) 0.0872(12) Uani 1 1 d . . . O3 O 0.0075(6) 1.0630(3) 0.7454(3) 0.0690(9) Uani 1 1 d . . . O2 O 0.0271(6) 0.8176(3) 0.7988(2) 0.0673(9) Uani 1 1 d . . . N4 N 0.2823(9) 0.9208(5) 0.8817(3) 0.0592(10) Uani 1 1 d . . . C2 C 0.7357(8) 0.8725(4) 0.5871(3) 0.0479(10) Uani 1 1 d . . . C3 C 0.9479(10) 0.6950(5) 0.5328(4) 0.0637(12) Uani 1 1 d . . . C1 C 0.4034(8) 0.9263(4) 0.6926(3) 0.0487(10) Uani 1 1 d . . . C4 C 1.1615(13) 0.6621(5) 0.4648(5) 0.0875(19) Uani 1 1 d . . . H4A H 1.2521 0.5757 0.4980 0.131 Uiso 1 1 calc R . . H4B H 1.2829 0.7269 0.4477 0.131 Uiso 1 1 calc R . . H4C H 1.0867 0.6627 0.4051 0.131 Uiso 1 1 calc R . . O4 O 1.3130(6) 0.6472(3) 0.0123(2) 0.0590(8) Uani 1 1 d . . . N6 N 1.2270(8) 0.4391(4) 0.0931(3) 0.0561(10) Uani 1 1 d D . . C5 C 0.9382(8) 0.6198(4) 0.1226(3) 0.0479(9) Uani 1 1 d . . . C10 C 1.1739(8) 0.5686(4) 0.0720(3) 0.0481(10) Uani 1 1 d . . . N5 N 0.6488(8) 0.8116(4) 0.1285(3) 0.0655(11) Uani 1 1 d . . . C6 C 0.8526(9) 0.7547(4) 0.0894(4) 0.0623(12) Uani 1 1 d . . . H6 H 0.9449 0.8090 0.0360 0.075 Uiso 1 1 calc R . . C9 C 0.8006(9) 0.5412(5) 0.2017(3) 0.0628(12) Uani 1 1 d . . . H9 H 0.8511 0.4501 0.2270 0.075 Uiso 1 1 calc R . . C7 C 0.5195(10) 0.7322(5) 0.2058(4) 0.0676(13) Uani 1 1 d . . . H7 H 0.3773 0.7703 0.2351 0.081 Uiso 1 1 calc R . . C8 C 0.5864(11) 0.5979(5) 0.2438(4) 0.0727(15) Uani 1 1 d . . . H8 H 0.4897 0.5457 0.2969 0.087 Uiso 1 1 calc R . . H6B H 1.360(6) 0.411(4) 0.066(3) 0.052(13) Uiso 1 1 d D . . H3A H 1.028(9) 0.870(4) 0.506(3) 0.053(13) Uiso 1 1 d . . . H6A H 1.125(7) 0.384(4) 0.128(3) 0.058(13) Uiso 1 1 d D . . H4F H 0.328(8) 0.986(5) 0.885(3) 0.046(13) Uiso 1 1 d . . . H4E H 0.320(10) 0.845(5) 0.918(4) 0.071(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0489(6) 0.0520(6) 0.0493(6) -0.0090(5) 0.0116(4) -0.0077(4) S2 0.0566(7) 0.0445(6) 0.0463(6) -0.0071(4) 0.0127(4) -0.0127(4) N2 0.061(2) 0.047(2) 0.0454(18) -0.0083(15) 0.0146(16) -0.0128(16) N3 0.062(2) 0.045(2) 0.0479(19) -0.0105(15) 0.0178(17) -0.0186(17) N1 0.059(2) 0.048(2) 0.0508(19) -0.0122(16) 0.0117(16) -0.0099(16) O1 0.113(3) 0.054(2) 0.094(3) -0.0278(19) 0.051(2) -0.032(2) O3 0.059(2) 0.065(2) 0.070(2) -0.0145(16) 0.0079(16) 0.0068(16) O2 0.064(2) 0.069(2) 0.066(2) -0.0170(16) 0.0129(16) -0.0228(16) N4 0.080(3) 0.048(2) 0.046(2) -0.0100(18) 0.0039(18) -0.014(2) C2 0.054(2) 0.048(2) 0.0348(18) -0.0042(16) 0.0054(17) -0.0124(18) C3 0.074(3) 0.053(3) 0.061(3) -0.017(2) 0.021(2) -0.018(2) C1 0.051(2) 0.047(2) 0.043(2) -0.0088(17) 0.0073(17) -0.0118(18) C4 0.106(4) 0.063(3) 0.094(4) -0.033(3) 0.049(4) -0.024(3) O4 0.0586(18) 0.0482(17) 0.0567(17) -0.0054(14) 0.0210(14) -0.0069(14) N6 0.053(2) 0.045(2) 0.059(2) -0.0087(17) 0.0180(18) -0.0030(17) C5 0.050(2) 0.046(2) 0.044(2) -0.0108(17) 0.0063(17) -0.0077(18) C10 0.047(2) 0.048(2) 0.043(2) -0.0081(17) 0.0040(17) -0.0064(18) N5 0.064(3) 0.055(2) 0.070(3) -0.0183(19) 0.022(2) -0.0044(19) C6 0.066(3) 0.052(3) 0.061(3) -0.014(2) 0.023(2) -0.009(2) C9 0.064(3) 0.057(3) 0.053(2) -0.007(2) 0.017(2) -0.003(2) C7 0.065(3) 0.071(3) 0.063(3) -0.024(2) 0.025(2) -0.009(2) C8 0.074(3) 0.067(3) 0.064(3) -0.013(2) 0.033(3) -0.008(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 S1 O3 1.419(3) . ? S1 O2 1.429(3) . ? S1 N4 1.572(4) . ? S1 C1 1.774(4) . ? S2 C2 1.719(4) . ? S2 C1 1.721(4) . ? N2 C2 1.302(5) . ? N2 N1 1.377(5) . ? N3 C3 1.355(6) . ? N3 C2 1.364(5) . ? N3 H3A 0.79(5) . ? N1 C1 1.292(5) . ? O1 C3 1.211(6) . ? N4 H4F 0.79(4) . ? N4 H4E 0.81(5) . ? C3 C4 1.495(7) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? O4 C10 1.239(5) . ? N6 C10 1.319(5) . ? N6 H6B 0.832(19) . ? N6 H6A 0.846(19) . ? C5 C9 1.370(6) . ? C5 C6 1.386(6) . ? C5 C10 1.499(6) . ? N5 C6 1.323(6) . ? N5 C7 1.337(6) . ? C6 H6 0.9300 . ? C9 C8 1.382(6) . ? C9 H9 0.9300 . ? C7 C8 1.366(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? 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 O3 S1 O2 121.4(2) . . ? O3 S1 N4 108.5(2) . . ? O2 S1 N4 108.5(2) . . ? O3 S1 C1 106.4(2) . . ? O2 S1 C1 103.6(2) . . ? N4 S1 C1 107.6(2) . . ? C2 S2 C1 85.42(19) . . ? C2 N2 N1 112.2(3) . . ? C3 N3 C2 124.2(4) . . ? C3 N3 H3A 122(3) . . ? C2 N3 H3A 113(3) . . ? C1 N1 N2 111.1(3) . . ? S1 N4 H4F 117(3) . . ? S1 N4 H4E 114(4) . . ? H4F N4 H4E 128(5) . . ? N2 C2 N3 120.8(4) . . ? N2 C2 S2 115.1(3) . . ? N3 C2 S2 124.0(3) . . ? O1 C3 N3 120.3(4) . . ? O1 C3 C4 124.7(5) . . ? N3 C3 C4 115.0(4) . . ? N1 C1 S2 116.2(3) . . ? N1 C1 S1 121.7(3) . . ? S2 C1 S1 122.0(2) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C10 N6 H6B 118(3) . . ? C10 N6 H6A 124(3) . . ? H6B N6 H6A 118(4) . . ? C9 C5 C6 116.9(4) . . ? C9 C5 C10 124.0(4) . . ? C6 C5 C10 119.1(4) . . ? O4 C10 N6 121.8(4) . . ? O4 C10 C5 120.1(4) . . ? N6 C10 C5 118.2(3) . . ? C6 N5 C7 117.0(4) . . ? N5 C6 C5 124.6(4) . . ? N5 C6 H6 117.7 . . ? C5 C6 H6 117.7 . . ? C5 C9 C8 119.7(4) . . ? C5 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? N5 C7 C8 123.1(4) . . ? N5 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? C7 C8 C9 118.7(4) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 67.07 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.407 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.075 data_ACZNAM2HP111 _database_code_depnum_ccdc_archive 'CCDC 1436981' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE;NICOTINAMIDE; 2 PYRIDONE' _chemical_melting_point 398 _chemical_formula_moiety 'C4H6N4O3S2,C6H6N2O,C5H5NO' _chemical_formula_sum 'C15 H17 N7 O5 S2' _chemical_formula_weight 439.48 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0347(3) _cell_length_b 10.2539(7) _cell_length_c 13.7934(9) _cell_angle_alpha 81.685(6) _cell_angle_beta 83.028(5) _cell_angle_gamma 88.283(5) _cell_volume 977.13(10) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3059 _cell_measurement_theta_min 4.3370 _cell_measurement_theta_max 71.7750 _exptl_crystal_description PLATE _exptl_crystal_colour COLORLES _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 2.872 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.37390 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5696 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 67.08 _reflns_number_total 3493 _reflns_number_gt 3085 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1265P)^2^+0.1831P] 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 3493 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1789 _refine_ls_wR_factor_gt 0.1729 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 S1 S 0.22992(10) 0.58018(6) 0.91819(4) 0.0443(2) Uani 1 1 d . . . S2 S 0.10956(11) 0.86219(6) 0.84318(5) 0.0509(3) Uani 1 1 d . . . N3 N 0.3772(3) 0.3583(2) 0.84479(15) 0.0432(5) Uani 1 1 d . . . H3A H 0.4276 0.3208 0.7958 0.052 Uiso 1 1 calc R . . N4 N -0.1101(4) 0.8589(3) 0.83042(18) 0.0542(6) Uani 1 1 d . . . H4D H -0.135(5) 0.874(4) 0.765(3) 0.065 Uiso 1 1 d . . . H4E H -0.169(5) 0.809(4) 0.875(3) 0.065 Uiso 1 1 d . . . O4 O 0.2932(3) 0.3349(2) 1.00854(14) 0.0579(6) Uani 1 1 d . . . N1 N 0.2665(4) 0.6787(2) 0.73554(17) 0.0532(6) Uani 1 1 d . . . O2 O 0.1267(4) 0.8680(2) 0.94448(18) 0.0756(7) Uani 1 1 d . . . N2 N 0.3323(4) 0.5504(2) 0.73756(17) 0.0529(6) Uani 1 1 d . . . C2 C 0.3203(4) 0.4885(3) 0.82671(17) 0.0398(5) Uani 1 1 d . . . O3 O 0.1975(4) 0.9579(2) 0.7666(2) 0.0748(7) Uani 1 1 d . . . C3 C 0.3579(4) 0.2863(3) 0.93588(19) 0.0449(6) Uani 1 1 d . . . C1 C 0.2122(4) 0.7064(3) 0.82222(19) 0.0432(6) Uani 1 1 d . . . C4 C 0.4247(6) 0.1463(3) 0.9399(2) 0.0640(9) Uani 1 1 d . . . H4A H 0.5228 0.1301 0.9831 0.096 Uiso 1 1 calc R . . H4B H 0.4755 0.1299 0.8750 0.096 Uiso 1 1 calc R . . H4C H 0.3190 0.0889 0.9644 0.096 Uiso 1 1 calc R . . O5 O 0.2092(4) 1.1295(2) 0.36200(15) 0.0630(6) Uani 1 1 d . . . N7 N 0.0777(4) 0.4994(2) 0.36778(17) 0.0498(6) Uani 1 1 d . . . H7A H 0.0756 0.4481 0.4231 0.060 Uiso 1 1 calc R . . N6 N 0.2013(3) 1.0862(2) 0.52532(17) 0.0502(6) Uani 1 1 d . . . H6B H 0.1589 1.1642 0.5325 0.060 Uiso 1 1 calc R . . H6A H 0.2210 1.0307 0.5762 0.060 Uiso 1 1 calc R . . O1 O -0.0862(4) 0.6521(2) 0.44814(15) 0.0629(6) Uani 1 1 d . . . C6 C 0.3112(4) 0.9151(3) 0.42818(18) 0.0398(5) Uani 1 1 d . . . N5 N 0.4717(3) 0.7672(2) 0.32463(16) 0.0477(5) Uani 1 1 d . . . C12 C 0.0046(5) 0.7021(3) 0.2751(2) 0.0540(7) Uani 1 1 d . . . H12 H -0.0488 0.7866 0.2708 0.065 Uiso 1 1 calc R . . C10 C 0.2361(4) 1.0519(3) 0.43622(19) 0.0424(6) Uani 1 1 d . . . C11 C -0.0067(4) 0.6203(3) 0.3685(2) 0.0491(6) Uani 1 1 d . . . C5 C 0.3970(4) 0.8856(3) 0.33832(18) 0.0444(6) Uani 1 1 d . . . H5 H 0.4032 0.9518 0.2843 0.053 Uiso 1 1 calc R . . C14 C 0.1743(5) 0.5306(3) 0.1967(2) 0.0579(7) Uani 1 1 d . . . H14 H 0.2330 0.5000 0.1400 0.069 Uiso 1 1 calc R . . C15 C 0.1651(4) 0.4540(3) 0.2854(2) 0.0521(7) Uani 1 1 d . . . H15 H 0.2189 0.3697 0.2902 0.063 Uiso 1 1 calc R . . C13 C 0.0925(5) 0.6582(3) 0.1922(2) 0.0575(7) Uani 1 1 d . . . H13 H 0.0986 0.7129 0.1320 0.069 Uiso 1 1 calc R . . C7 C 0.3000(5) 0.8162(3) 0.5076(2) 0.0555(7) Uani 1 1 d . . . H7 H 0.2422 0.8318 0.5692 0.067 Uiso 1 1 calc R . . C8 C 0.3758(6) 0.6939(3) 0.4942(2) 0.0658(9) Uani 1 1 d . . . H8 H 0.3688 0.6255 0.5466 0.079 Uiso 1 1 calc R . . C9 C 0.4616(5) 0.6739(3) 0.4030(2) 0.0547(7) Uani 1 1 d . . . H9 H 0.5153 0.5915 0.3954 0.066 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 S1 0.0696(5) 0.0335(4) 0.0282(4) -0.0030(2) -0.0027(3) 0.0075(3) S2 0.0774(5) 0.0294(4) 0.0448(4) -0.0038(3) -0.0058(3) 0.0050(3) N3 0.0577(12) 0.0366(11) 0.0318(11) -0.0025(8) 0.0030(8) 0.0107(9) N4 0.0779(17) 0.0439(13) 0.0353(12) 0.0029(10) 0.0025(11) 0.0137(11) O4 0.0930(15) 0.0422(11) 0.0336(10) -0.0007(8) 0.0032(9) 0.0111(10) N1 0.0773(16) 0.0404(12) 0.0358(12) 0.0026(9) 0.0048(10) 0.0141(11) O2 0.122(2) 0.0509(13) 0.0616(15) -0.0222(11) -0.0293(14) 0.0163(13) N2 0.0769(16) 0.0417(13) 0.0336(11) 0.0028(9) 0.0063(10) 0.0163(11) C2 0.0487(13) 0.0381(13) 0.0299(12) -0.0022(9) 0.0010(9) 0.0063(10) O3 0.0926(17) 0.0371(11) 0.0856(18) 0.0099(11) 0.0049(13) -0.0042(11) C3 0.0578(15) 0.0377(13) 0.0368(13) -0.0020(10) -0.0016(11) 0.0057(11) C1 0.0598(15) 0.0319(12) 0.0353(13) -0.0001(10) -0.0018(10) 0.0042(10) C4 0.099(2) 0.0414(17) 0.0458(16) 0.0013(12) 0.0004(15) 0.0157(16) O5 0.1071(17) 0.0416(11) 0.0384(11) -0.0005(9) -0.0126(10) 0.0224(11) N7 0.0734(15) 0.0398(12) 0.0368(11) -0.0080(9) -0.0077(10) 0.0072(10) N6 0.0714(15) 0.0380(12) 0.0418(12) -0.0091(9) -0.0086(10) 0.0150(10) O1 0.0994(16) 0.0466(12) 0.0427(11) -0.0127(9) -0.0076(10) 0.0234(11) C6 0.0465(13) 0.0368(13) 0.0347(12) -0.0041(10) -0.0020(9) 0.0067(10) N5 0.0618(13) 0.0444(12) 0.0349(11) -0.0080(9) 0.0023(9) 0.0118(10) C12 0.0746(18) 0.0397(14) 0.0487(16) -0.0040(12) -0.0145(13) 0.0032(13) C10 0.0512(13) 0.0365(13) 0.0388(13) -0.0036(10) -0.0058(10) 0.0057(10) C11 0.0672(16) 0.0400(14) 0.0430(15) -0.0125(11) -0.0126(12) 0.0075(12) C5 0.0578(15) 0.0414(14) 0.0318(12) -0.0021(10) -0.0024(10) 0.0078(11) C14 0.0686(18) 0.0632(19) 0.0425(15) -0.0159(13) 0.0004(13) -0.0006(14) C15 0.0656(17) 0.0440(15) 0.0483(15) -0.0154(12) -0.0040(12) 0.0063(12) C13 0.0710(18) 0.0577(18) 0.0420(15) 0.0013(13) -0.0086(13) -0.0062(14) C7 0.085(2) 0.0436(15) 0.0316(13) -0.0008(11) 0.0092(12) 0.0167(13) C8 0.105(3) 0.0426(17) 0.0405(16) 0.0050(12) 0.0094(15) 0.0237(16) C9 0.0780(19) 0.0385(14) 0.0438(15) -0.0049(12) 0.0020(13) 0.0180(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 S1 C1 1.726(2) . ? S1 C2 1.730(2) . ? S2 O2 1.427(2) . ? S2 O3 1.428(2) . ? S2 N4 1.578(3) . ? S2 C1 1.781(3) . ? N3 C3 1.356(3) . ? N3 C2 1.379(3) . ? O4 C3 1.216(3) . ? N1 C1 1.279(3) . ? N1 N2 1.379(3) . ? N2 C2 1.294(3) . ? C3 C4 1.493(4) . ? O5 C10 1.233(3) . ? N7 C11 1.359(4) . ? N7 C15 1.361(4) . ? N6 C10 1.320(3) . ? O1 C11 1.253(3) . ? C6 C7 1.377(4) . ? C6 C5 1.381(3) . ? C6 C10 1.499(3) . ? N5 C9 1.332(4) . ? N5 C5 1.338(3) . ? C12 C13 1.361(4) . ? C12 C11 1.427(4) . ? C14 C15 1.351(4) . ? C14 C13 1.409(5) . ? C7 C8 1.376(4) . ? C8 C9 1.368(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C2 84.93(12) . . ? O2 S2 O3 121.32(18) . . ? O2 S2 N4 108.37(16) . . ? O3 S2 N4 107.68(15) . . ? O2 S2 C1 104.20(13) . . ? O3 S2 C1 106.83(14) . . ? N4 S2 C1 107.75(14) . . ? C3 N3 C2 123.4(2) . . ? C1 N1 N2 111.9(2) . . ? C2 N2 N1 111.6(2) . . ? N2 C2 N3 120.8(2) . . ? N2 C2 S1 115.5(2) . . ? N3 C2 S1 123.76(18) . . ? O4 C3 N3 121.4(2) . . ? O4 C3 C4 123.2(2) . . ? N3 C3 C4 115.3(2) . . ? N1 C1 S1 116.1(2) . . ? N1 C1 S2 122.40(19) . . ? S1 C1 S2 121.40(15) . . ? C11 N7 C15 124.4(3) . . ? C7 C6 C5 117.9(2) . . ? C7 C6 C10 122.6(2) . . ? C5 C6 C10 119.5(2) . . ? C9 N5 C5 117.2(2) . . ? C13 C12 C11 120.8(3) . . ? O5 C10 N6 121.4(3) . . ? O5 C10 C6 121.0(2) . . ? N6 C10 C6 117.6(2) . . ? O1 C11 N7 119.5(3) . . ? O1 C11 C12 125.1(3) . . ? N7 C11 C12 115.4(3) . . ? N5 C5 C6 123.6(2) . . ? C15 C14 C13 118.2(3) . . ? C14 C15 N7 120.5(3) . . ? C12 C13 C14 120.8(3) . . ? C8 C7 C6 118.8(3) . . ? C9 C8 C7 119.4(3) . . ? N5 C9 C8 122.9(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.08 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.800 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.117 data_ACZOMeHPH111 _database_code_depnum_ccdc_archive 'CCDC 1436979' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE; 3 OME 2 PYRIDONE' _chemical_melting_point 363 _chemical_formula_moiety 'C4H6N4O3S2,C6H7NO2,H2O' _chemical_formula_sum 'C10 H15 N5 O6 S2' _chemical_formula_weight 365.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7872(6) _cell_length_b 10.2130(7) _cell_length_c 10.2464(7) _cell_angle_alpha 88.192(5) _cell_angle_beta 76.587(6) _cell_angle_gamma 77.996(6) _cell_volume 775.22(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2221 _cell_measurement_theta_min 4.3990 _cell_measurement_theta_max 71.6160 _exptl_crystal_description PLATE _exptl_crystal_colour COLORLES _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 3.493 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.52975 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4182 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.43 _diffrn_reflns_theta_max 67.06 _reflns_number_total 2734 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1021P)^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 2734 _refine_ls_number_parameters 234 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.061 _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 S2 S 0.74682(8) 0.29948(6) 0.41441(5) 0.0401(2) Uani 1 1 d . . . S1 S 0.89362(8) 0.29672(6) 0.11297(5) 0.0375(2) Uani 1 1 d . . . O3 O 0.6751(3) 0.42953(19) 0.3709(2) 0.0599(6) Uani 1 1 d . . . O5 O 0.5802(2) 0.08098(17) 0.15601(17) 0.0447(4) Uani 1 1 d . . . O4 O 0.3422(2) 0.29976(16) 0.26201(16) 0.0444(4) Uani 1 1 d . . . N4 N 0.5914(3) 0.2185(3) 0.4532(2) 0.0460(5) Uani 1 1 d . . . N3 N 1.1399(3) 0.1432(2) -0.08603(19) 0.0364(4) Uani 1 1 d . . . N5 N 0.5962(3) 0.16290(19) -0.0548(2) 0.0378(4) Uani 1 1 d . . . O6 O 0.3340(3) 0.0077(2) 0.3844(2) 0.0602(6) Uani 1 1 d D . . C7 C 0.3504(3) 0.3883(2) 0.0383(2) 0.0375(5) Uani 1 1 d . . . H7 H 0.2658 0.4658 0.0697 0.045 Uiso 1 1 calc R . . O1 O 0.9721(3) 0.3295(2) -0.1467(2) 0.0653(6) Uani 1 1 d . . . O2 O 0.8426(3) 0.2846(2) 0.51861(19) 0.0592(5) Uani 1 1 d . . . N2 N 1.1116(3) 0.0757(2) 0.1363(2) 0.0398(5) Uani 1 1 d . . . C5 C 0.4011(3) 0.2938(2) 0.1270(2) 0.0336(5) Uani 1 1 d . . . C1 C 0.8998(3) 0.2235(2) 0.2664(2) 0.0365(5) Uani 1 1 d . . . N1 N 1.0156(3) 0.1136(2) 0.2650(2) 0.0414(5) Uani 1 1 d . . . C3 C 1.0888(3) 0.2312(3) -0.1803(2) 0.0436(6) Uani 1 1 d . . . C2 C 1.0616(3) 0.1613(2) 0.0475(2) 0.0322(5) Uani 1 1 d . . . C8 C 0.4252(4) 0.3693(2) -0.1000(3) 0.0437(6) Uani 1 1 d . . . H8 H 0.3893 0.4333 -0.1603 0.052 Uiso 1 1 calc R . . C6 C 0.5303(3) 0.1729(2) 0.0796(2) 0.0338(5) Uani 1 1 d . . . C4 C 1.1868(5) 0.1965(4) -0.3222(3) 0.0627(8) Uani 1 1 d . . . H4A H 1.1012 0.1972 -0.3764 0.094 Uiso 1 1 calc R . . H4B H 1.2627 0.1089 -0.3263 0.094 Uiso 1 1 calc R . . H4C H 1.2596 0.2609 -0.3553 0.094 Uiso 1 1 calc R . . C9 C 0.5493(4) 0.2576(3) -0.1445(2) 0.0418(5) Uani 1 1 d . . . H9 H 0.6026 0.2450 -0.2355 0.050 Uiso 1 1 calc R . . C13 C 0.2285(4) 0.4222(3) 0.3220(3) 0.0506(7) Uani 1 1 d . . . H13A H 0.2920 0.4941 0.3008 0.076 Uiso 1 1 calc R . . H13B H 0.1960 0.4130 0.4176 0.076 Uiso 1 1 calc R . . H13C H 0.1213 0.4415 0.2878 0.076 Uiso 1 1 calc R . . H4D H 0.620(5) 0.149(4) 0.489(4) 0.057(9) Uiso 1 1 d . . . H4E H 0.529(5) 0.211(4) 0.390(4) 0.078(11) Uiso 1 1 d . . . H5A H 0.683(4) 0.087(3) -0.081(3) 0.048(8) Uiso 1 1 d . . . H3A H 1.217(4) 0.076(3) -0.109(3) 0.042(7) Uiso 1 1 d . . . H6B H 0.220(3) 0.043(4) 0.379(4) 0.080(12) Uiso 1 1 d D . . H6A H 0.405(4) 0.045(3) 0.314(3) 0.060(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S2 0.0419(4) 0.0430(4) 0.0311(3) -0.0028(2) -0.0039(2) -0.0038(3) S1 0.0348(4) 0.0377(3) 0.0338(3) 0.0020(2) -0.0040(2) 0.0016(2) O3 0.0725(14) 0.0416(10) 0.0502(11) 0.0007(8) 0.0055(10) 0.0010(9) O5 0.0497(10) 0.0350(9) 0.0407(9) 0.0038(7) -0.0057(8) 0.0050(7) O4 0.0552(11) 0.0357(9) 0.0347(9) -0.0008(7) -0.0071(8) 0.0039(8) N4 0.0402(12) 0.0567(14) 0.0375(11) 0.0079(10) -0.0063(9) -0.0061(10) N3 0.0340(11) 0.0374(10) 0.0326(10) -0.0007(8) -0.0031(8) -0.0006(9) N5 0.0427(11) 0.0302(10) 0.0378(10) -0.0028(8) -0.0076(8) -0.0029(8) O6 0.0564(13) 0.0674(13) 0.0529(11) 0.0228(10) -0.0136(10) -0.0058(10) C7 0.0392(13) 0.0285(11) 0.0445(12) 0.0018(9) -0.0115(10) -0.0046(9) O1 0.0630(13) 0.0660(13) 0.0457(10) 0.0097(9) -0.0053(9) 0.0249(11) O2 0.0592(12) 0.0803(14) 0.0407(10) -0.0114(9) -0.0160(9) -0.0134(10) N2 0.0410(11) 0.0374(10) 0.0356(10) 0.0018(8) -0.0047(8) -0.0006(8) C5 0.0352(12) 0.0299(11) 0.0367(11) -0.0022(9) -0.0086(9) -0.0079(9) C1 0.0333(12) 0.0406(12) 0.0342(11) 0.0007(9) -0.0064(9) -0.0062(9) N1 0.0395(11) 0.0433(11) 0.0359(10) 0.0020(8) -0.0033(8) -0.0025(9) C3 0.0379(13) 0.0531(15) 0.0359(12) 0.0041(10) -0.0075(10) -0.0022(11) C2 0.0293(11) 0.0314(11) 0.0355(11) 0.0008(9) -0.0063(9) -0.0068(8) C8 0.0546(16) 0.0366(13) 0.0418(13) 0.0090(10) -0.0163(11) -0.0086(11) C6 0.0353(12) 0.0309(11) 0.0364(11) 0.0014(9) -0.0094(9) -0.0083(9) C4 0.0592(18) 0.081(2) 0.0347(14) 0.0058(13) -0.0069(12) 0.0094(15) C9 0.0492(15) 0.0418(13) 0.0344(11) 0.0007(10) -0.0081(10) -0.0111(10) C13 0.0557(17) 0.0435(14) 0.0423(13) -0.0061(11) -0.0019(12) 0.0030(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S2 O2 1.4252(19) . ? S2 O3 1.430(2) . ? S2 N4 1.575(2) . ? S2 C1 1.781(2) . ? S1 C2 1.724(2) . ? S1 C1 1.726(2) . ? O5 C6 1.260(3) . ? O4 C5 1.352(3) . ? O4 C13 1.436(3) . ? N4 H4D 0.80(4) . ? N4 H4E 0.91(4) . ? N3 C2 1.363(3) . ? N3 C3 1.369(3) . ? N3 H3A 0.81(3) . ? N5 C6 1.352(3) . ? N5 C9 1.366(3) . ? N5 H5A 0.92(3) . ? O6 H6B 0.902(18) . ? O6 H6A 0.923(18) . ? C7 C5 1.366(3) . ? C7 C8 1.404(3) . ? C7 H7 0.9300 . ? O1 C3 1.204(3) . ? N2 C2 1.310(3) . ? N2 N1 1.380(3) . ? C5 C6 1.438(3) . ? C1 N1 1.284(3) . ? C3 C4 1.493(4) . ? C8 C9 1.347(4) . ? C8 H8 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C9 H9 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 O2 S2 O3 120.66(13) . . ? O2 S2 N4 108.27(13) . . ? O3 S2 N4 109.07(14) . . ? O2 S2 C1 107.37(12) . . ? O3 S2 C1 103.16(11) . . ? N4 S2 C1 107.58(12) . . ? C2 S1 C1 85.36(11) . . ? C5 O4 C13 117.92(18) . . ? S2 N4 H4D 114(2) . . ? S2 N4 H4E 117(2) . . ? H4D N4 H4E 112(3) . . ? C2 N3 C3 122.3(2) . . ? C2 N3 H3A 118(2) . . ? C3 N3 H3A 120(2) . . ? C6 N5 C9 125.0(2) . . ? C6 N5 H5A 113.3(19) . . ? C9 N5 H5A 121.7(19) . . ? H6B O6 H6A 105(3) . . ? C5 C7 C8 120.5(2) . . ? C5 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C2 N2 N1 111.88(19) . . ? O4 C5 C7 126.7(2) . . ? O4 C5 C6 112.98(19) . . ? C7 C5 C6 120.3(2) . . ? N1 C1 S1 116.32(18) . . ? N1 C1 S2 123.92(18) . . ? S1 C1 S2 119.75(14) . . ? C1 N1 N2 111.50(19) . . ? O1 C3 N3 120.2(2) . . ? O1 C3 C4 124.0(2) . . ? N3 C3 C4 115.7(2) . . ? N2 C2 N3 121.5(2) . . ? N2 C2 S1 114.94(17) . . ? N3 C2 S1 123.57(17) . . ? C9 C8 C7 119.4(2) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? O5 C6 N5 121.3(2) . . ? O5 C6 C5 123.3(2) . . ? N5 C6 C5 115.4(2) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C8 C9 N5 119.5(2) . . ? C8 C9 H9 120.3 . . ? N5 C9 H9 120.3 . . ? O4 C13 H13A 109.5 . . ? O4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 67.06 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.414 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.094 data_ACZVLM12 _database_code_depnum_ccdc_archive 'CCDC 1436978' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ACETAZOLAMIDE; VALEROLACTAM' _chemical_melting_point 366 _chemical_formula_moiety C4H6N4O3S2,2(C5H9NO) _chemical_formula_sum 'C14 H24 N6 O5 S2' _chemical_formula_weight 420.51 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' _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 9.66166(19) _cell_length_b 23.4685(4) _cell_length_c 8.84352(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.7730(19) _cell_angle_gamma 90.00 _cell_volume 1969.88(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3314 _cell_measurement_theta_min 4.6530 _cell_measurement_theta_max 71.6200 _exptl_crystal_description needle _exptl_crystal_colour colorles _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 2.797 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.70175 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6492 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 67.05 _reflns_number_total 3507 _reflns_number_gt 3068 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.4712P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3507 _refine_ls_number_parameters 266 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.05603(6) 0.70069(2) 0.86906(7) 0.04789(19) Uani 1 1 d . . . S2 S 0.10589(6) 0.57207(2) 0.85192(7) 0.04876(19) Uani 1 1 d . . . N1 N 0.1709(2) 0.80103(8) 0.7959(2) 0.0458(4) Uani 1 1 d . . . O5 O 0.47643(18) 0.51554(7) 0.8041(2) 0.0573(4) Uani 1 1 d . . . O1 O -0.00847(19) 0.80761(8) 0.9245(2) 0.0648(5) Uani 1 1 d . . . C3 C 0.0787(2) 0.83161(10) 0.8649(3) 0.0477(5) Uani 1 1 d . . . N6 N 0.4989(2) 0.59455(9) 0.6701(3) 0.0540(5) Uani 1 1 d . . . O2 O 0.00146(19) 0.57761(8) 0.9450(3) 0.0687(5) Uani 1 1 d . . . N4 N 0.2449(2) 0.54589(8) 0.9520(3) 0.0490(5) Uani 1 1 d D . . N2 N 0.2659(2) 0.71498(8) 0.7328(3) 0.0545(5) Uani 1 1 d . . . C2 C 0.1729(2) 0.74257(9) 0.7927(2) 0.0422(5) Uani 1 1 d . . . N3 N 0.2489(2) 0.65681(8) 0.7445(3) 0.0547(5) Uani 1 1 d . . . C10 C 0.5413(2) 0.54307(9) 0.7199(3) 0.0437(5) Uani 1 1 d . . . O3 O 0.0768(2) 0.54194(8) 0.7106(2) 0.0722(5) Uani 1 1 d . . . C12 C 0.7225(3) 0.55117(12) 0.5462(3) 0.0606(6) Uani 1 1 d . . . H12A H 0.8188 0.5403 0.5430 0.073 Uiso 1 1 calc R . . H12B H 0.6642 0.5417 0.4478 0.073 Uiso 1 1 calc R . . C4 C 0.0960(3) 0.89508(11) 0.8610(3) 0.0607(6) Uani 1 1 d . . . H4A H 0.0285 0.9129 0.9127 0.091 Uiso 1 1 calc R . . H4B H 0.0812 0.9078 0.7560 0.091 Uiso 1 1 calc R . . H4C H 0.1895 0.9052 0.9118 0.091 Uiso 1 1 calc R . . C1 C 0.1459(2) 0.64398(9) 0.8114(3) 0.0449(5) Uani 1 1 d . . . C11 C 0.6716(3) 0.51911(10) 0.6736(3) 0.0543(6) Uani 1 1 d . . . H11A H 0.6529 0.4799 0.6410 0.065 Uiso 1 1 calc R . . H11B H 0.7466 0.5186 0.7634 0.065 Uiso 1 1 calc R . . C13 C 0.7154(3) 0.61411(12) 0.5745(4) 0.0677(7) Uani 1 1 d . . . H13A H 0.7516 0.6348 0.4952 0.081 Uiso 1 1 calc R . . H13B H 0.7733 0.6235 0.6732 0.081 Uiso 1 1 calc R . . C14 C 0.5652(3) 0.63159(11) 0.5733(4) 0.0691(8) Uani 1 1 d . . . H14A H 0.5634 0.6705 0.6097 0.083 Uiso 1 1 calc R . . H14B H 0.5124 0.6302 0.4687 0.083 Uiso 1 1 calc R . . O4 O 0.36338(16) 0.63381(7) 0.1712(2) 0.0548(4) Uani 1 1 d . . . N5 N 0.5710(2) 0.60207(8) 0.1312(2) 0.0488(5) Uani 1 1 d . . . C9 C 0.4827(2) 0.64362(9) 0.1412(3) 0.0439(5) Uani 1 1 d . . . C5 C 0.7137(3) 0.60708(11) 0.1001(4) 0.0620(7) Uani 1 1 d . . . H5A H 0.7244 0.5811 0.0178 0.074 Uiso 1 1 calc R . . H5B H 0.7806 0.5960 0.1913 0.074 Uiso 1 1 calc R . . C8 C 0.5261(3) 0.70361(10) 0.1132(4) 0.0650(7) Uani 1 1 d . . . H8A H 0.4698 0.7170 0.0174 0.078 Uiso 1 1 calc R . . H8B H 0.5053 0.7277 0.1952 0.078 Uiso 1 1 calc R . . C7 C 0.6773(4) 0.71018(14) 0.1049(9) 0.152(3) Uani 1 1 d . . . H7A H 0.6853 0.7421 0.0375 0.182 Uiso 1 1 calc R . . H7B H 0.7272 0.7206 0.2067 0.182 Uiso 1 1 calc R . . C6 C 0.7463(4) 0.66532(14) 0.0560(6) 0.0999(13) Uani 1 1 d . . . H6A H 0.8463 0.6714 0.0919 0.120 Uiso 1 1 calc R . . H6B H 0.7298 0.6668 -0.0556 0.120 Uiso 1 1 calc R . . H5C H 0.541(3) 0.5676(11) 0.145(3) 0.050(7) Uiso 1 1 d . . . H4E H 0.274(3) 0.5665(12) 1.040(3) 0.075(9) Uiso 1 1 d D . . H4D H 0.303(3) 0.5368(11) 0.902(3) 0.052(7) Uiso 1 1 d . . . H1A H 0.232(3) 0.8176(12) 0.753(3) 0.055(7) Uiso 1 1 d . . . H6C H 0.427(3) 0.6059(13) 0.700(3) 0.061(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0429(3) 0.0456(3) 0.0613(4) 0.0037(2) 0.0257(3) -0.0024(2) S2 0.0439(3) 0.0428(3) 0.0609(4) 0.0042(2) 0.0131(2) -0.0060(2) N1 0.0430(10) 0.0423(10) 0.0571(11) 0.0047(8) 0.0218(9) -0.0013(8) O5 0.0625(10) 0.0437(8) 0.0732(11) 0.0080(8) 0.0320(9) -0.0004(7) O1 0.0583(10) 0.0609(11) 0.0858(13) -0.0046(9) 0.0405(10) -0.0025(8) C3 0.0439(11) 0.0491(12) 0.0526(12) -0.0021(10) 0.0156(10) -0.0007(10) N6 0.0535(11) 0.0445(11) 0.0701(13) 0.0085(9) 0.0271(10) 0.0081(9) O2 0.0521(9) 0.0591(10) 0.1037(15) 0.0153(10) 0.0370(10) -0.0033(8) N4 0.0519(11) 0.0432(10) 0.0545(12) 0.0044(9) 0.0164(10) 0.0000(8) N2 0.0507(11) 0.0444(10) 0.0761(14) 0.0094(10) 0.0319(10) 0.0022(8) C2 0.0362(10) 0.0463(11) 0.0473(11) 0.0067(9) 0.0159(8) -0.0004(9) N3 0.0521(11) 0.0446(10) 0.0748(13) 0.0066(9) 0.0308(10) 0.0036(8) C10 0.0449(11) 0.0395(11) 0.0485(12) -0.0017(9) 0.0133(9) -0.0021(9) O3 0.0820(13) 0.0607(11) 0.0677(12) -0.0040(9) -0.0017(10) -0.0143(10) C12 0.0527(13) 0.0741(17) 0.0592(15) -0.0026(13) 0.0212(12) 0.0016(12) C4 0.0641(15) 0.0484(13) 0.0748(17) -0.0063(12) 0.0266(13) -0.0006(11) C1 0.0399(10) 0.0424(11) 0.0543(12) 0.0053(9) 0.0142(9) 0.0013(9) C11 0.0525(13) 0.0471(12) 0.0668(15) 0.0010(11) 0.0203(11) 0.0077(10) C13 0.0672(16) 0.0663(17) 0.0769(18) 0.0068(14) 0.0324(14) -0.0137(13) C14 0.0805(18) 0.0532(14) 0.0818(19) 0.0218(13) 0.0360(15) 0.0091(13) O4 0.0429(8) 0.0503(9) 0.0762(11) -0.0110(8) 0.0242(8) -0.0031(7) N5 0.0435(10) 0.0383(10) 0.0685(13) 0.0014(9) 0.0208(9) 0.0012(8) C9 0.0420(10) 0.0425(11) 0.0495(12) -0.0046(9) 0.0145(9) 0.0002(9) C5 0.0473(13) 0.0534(14) 0.093(2) 0.0005(13) 0.0319(13) 0.0055(11) C8 0.0570(15) 0.0399(12) 0.103(2) 0.0015(13) 0.0289(15) 0.0026(10) C7 0.095(3) 0.0478(17) 0.345(9) 0.022(3) 0.125(4) 0.0019(18) C6 0.074(2) 0.0688(19) 0.178(4) 0.010(2) 0.078(2) -0.0040(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.718(2) . ? S1 C2 1.727(2) . ? S2 O3 1.418(2) . ? S2 O2 1.4223(19) . ? S2 N4 1.587(2) . ? S2 C1 1.782(2) . ? N1 C2 1.373(3) . ? N1 C3 1.373(3) . ? N1 H1A 0.85(3) . ? O5 C10 1.240(3) . ? O1 C3 1.212(3) . ? C3 C4 1.500(3) . ? N6 C10 1.324(3) . ? N6 C14 1.451(3) . ? N6 H6C 0.83(3) . ? N4 H4E 0.913(18) . ? N4 H4D 0.81(3) . ? N2 C2 1.297(3) . ? N2 N3 1.381(3) . ? N3 C1 1.285(3) . ? C10 C11 1.503(3) . ? C12 C13 1.502(4) . ? C12 C11 1.512(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 C14 1.506(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O4 C9 1.251(3) . ? N5 C9 1.309(3) . ? N5 C5 1.460(3) . ? N5 H5C 0.87(3) . ? C9 C8 1.503(3) . ? C5 C6 1.471(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C8 C7 1.484(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 C6 1.359(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 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 C1 S1 C2 85.48(10) . . ? O3 S2 O2 120.72(13) . . ? O3 S2 N4 107.82(13) . . ? O2 S2 N4 109.29(13) . . ? O3 S2 C1 108.04(11) . . ? O2 S2 C1 103.50(10) . . ? N4 S2 C1 106.61(10) . . ? C2 N1 C3 123.02(19) . . ? C2 N1 H1A 115.7(19) . . ? C3 N1 H1A 121.3(19) . . ? O1 C3 N1 120.8(2) . . ? O1 C3 C4 124.1(2) . . ? N1 C3 C4 115.1(2) . . ? C10 N6 C14 126.8(2) . . ? C10 N6 H6C 114(2) . . ? C14 N6 H6C 119(2) . . ? S2 N4 H4E 111.5(19) . . ? S2 N4 H4D 113.4(19) . . ? H4E N4 H4D 118(3) . . ? C2 N2 N3 111.20(18) . . ? N2 C2 N1 121.41(19) . . ? N2 C2 S1 115.38(17) . . ? N1 C2 S1 123.20(16) . . ? C1 N3 N2 112.29(18) . . ? O5 C10 N6 121.0(2) . . ? O5 C10 C11 120.7(2) . . ? N6 C10 C11 118.3(2) . . ? C13 C12 C11 109.5(2) . . ? C13 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? C13 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C1 S1 115.65(17) . . ? N3 C1 S2 122.00(17) . . ? S1 C1 S2 122.25(12) . . ? C10 C11 C12 115.0(2) . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C12 C13 C14 109.9(2) . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N6 C14 C13 111.3(2) . . ? N6 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? N6 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C9 N5 C5 127.1(2) . . ? C9 N5 H5C 116.5(17) . . ? C5 N5 H5C 116.4(17) . . ? O4 C9 N5 121.0(2) . . ? O4 C9 C8 120.3(2) . . ? N5 C9 C8 118.7(2) . . ? N5 C5 C6 112.4(2) . . ? N5 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N5 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C7 C8 C9 114.4(2) . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C6 C7 C8 118.7(3) . . ? C6 C7 H7A 107.6 . . ? C8 C7 H7A 107.6 . . ? C6 C7 H7B 107.6 . . ? C8 C7 H7B 107.6 . . ? H7A C7 H7B 107.1 . . ? C7 C6 C5 119.5(3) . . ? C7 C6 H6A 107.4 . . ? C5 C6 H6A 107.4 . . ? C7 C6 H6B 107.4 . . ? C5 C6 H6B 107.4 . . ? H6A C6 H6B 107.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 67.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.366 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.047