# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Gellert Mezei' _publ_contact_author_email gellert.mezei@wmich.edu loop_ _publ_author_name I.Fernando S.Jianrattanasawat D.Sarut N.Daskalakis K.Demadis G.Mezei data_zincpyrazolesulfonate _database_code_depnum_ccdc_archive 'CCDC 837807' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 N4 O8 S2 Zn' _chemical_formula_weight 395.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2109(8) _cell_length_b 7.3813(9) _cell_length_c 7.3993(9) _cell_angle_alpha 61.433(2) _cell_angle_beta 66.100(2) _cell_angle_gamma 71.148(2) _cell_volume 312.10(6) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 2.351 _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_reflns_number 1348 _diffrn_reflns_av_R_equivalents 0.0111 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 23.25 _reflns_number_total 892 _reflns_number_gt 878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0431P)^2^+0.3164P] 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 892 _refine_ls_number_parameters 103 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.0000 1.0000 1.0000 0.0170(2) Uani 1 2 d S . . S1 S 0.33476(10) 0.72855(10) 1.27381(10) 0.0151(2) Uani 1 1 d . . . O1 O 0.2831(3) 0.8790(3) 1.0748(3) 0.0201(5) Uani 1 1 d . . . O2 O 0.1998(3) 0.5718(3) 1.4057(3) 0.0226(5) Uani 1 1 d . . . O3 O 0.5505(3) 0.6396(3) 1.2268(3) 0.0242(5) Uani 1 1 d . . . O4 O 0.0607(3) 1.3040(3) 0.8719(3) 0.0227(5) Uani 1 1 d D . . H4A H 0.179(3) 1.314(5) 0.840(5) 0.027 Uiso 1 1 d D . . H4B H 0.012(5) 1.382(5) 0.773(4) 0.027 Uiso 1 1 d D . . N1 N 0.1652(4) 0.9794(4) 0.6944(4) 0.0184(5) Uani 1 1 d . . . N2 N 0.2471(4) 1.1331(4) 0.5053(4) 0.0205(6) Uani 1 1 d . . . H2 H 0.2529 1.2531 0.4931 0.025 Uiso 1 1 calc R . . C1 C 0.3173(4) 1.0761(5) 0.3408(5) 0.0212(7) Uani 1 1 d . . . H1 H 0.3782 1.1571 0.1970 0.025 Uiso 1 1 calc R . . C2 C 0.2830(4) 0.8756(4) 0.4231(4) 0.0171(6) Uani 1 1 d . . . C3 C 0.1891(4) 0.8205(5) 0.6442(4) 0.0197(6) Uani 1 1 d . . . H3 H 0.1489 0.6915 0.7425 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0197(3) 0.0165(3) 0.0156(3) -0.0079(2) -0.0044(2) -0.00299(19) S1 0.0156(4) 0.0152(4) 0.0155(4) -0.0075(3) -0.0045(3) -0.0018(3) O1 0.0195(10) 0.0245(11) 0.0172(10) -0.0084(9) -0.0071(8) -0.0025(8) O2 0.0259(11) 0.0188(11) 0.0235(11) -0.0082(9) -0.0055(9) -0.0069(9) O3 0.0182(11) 0.0264(11) 0.0290(12) -0.0152(9) -0.0066(9) 0.0009(9) O4 0.0242(12) 0.0211(11) 0.0228(11) -0.0065(9) -0.0084(9) -0.0056(9) N1 0.0207(13) 0.0184(12) 0.0165(12) -0.0079(10) -0.0047(10) -0.0032(10) N2 0.0258(14) 0.0167(12) 0.0204(13) -0.0092(11) -0.0036(11) -0.0067(10) C1 0.0233(16) 0.0202(15) 0.0166(15) -0.0071(12) -0.0014(12) -0.0056(12) C2 0.0174(14) 0.0174(15) 0.0185(15) -0.0089(12) -0.0065(12) -0.0013(11) C3 0.0216(15) 0.0180(14) 0.0194(16) -0.0087(12) -0.0057(13) -0.0017(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 Zn1 O4 2.095(2) 2_577 ? Zn1 O4 2.095(2) . ? Zn1 O1 2.1295(19) 2_577 ? Zn1 O1 2.1295(19) . ? Zn1 N1 2.141(2) 2_577 ? Zn1 N1 2.141(2) . ? S1 O3 1.446(2) . ? S1 O2 1.455(2) . ? S1 O1 1.468(2) . ? S1 C2 1.757(3) 1_556 ? N1 C3 1.333(4) . ? N1 N2 1.356(3) . ? N2 C1 1.329(4) . ? C1 C2 1.369(4) . ? C2 C3 1.394(4) . ? C2 S1 1.757(3) 1_554 ? 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 O4 Zn1 O4 179.999(1) 2_577 . ? O4 Zn1 O1 89.60(8) 2_577 2_577 ? O4 Zn1 O1 90.40(8) . 2_577 ? O4 Zn1 O1 90.40(8) 2_577 . ? O4 Zn1 O1 89.60(8) . . ? O1 Zn1 O1 180.00(4) 2_577 . ? O4 Zn1 N1 90.64(8) 2_577 2_577 ? O4 Zn1 N1 89.36(8) . 2_577 ? O1 Zn1 N1 87.55(8) 2_577 2_577 ? O1 Zn1 N1 92.45(8) . 2_577 ? O4 Zn1 N1 89.36(8) 2_577 . ? O4 Zn1 N1 90.64(9) . . ? O1 Zn1 N1 92.45(8) 2_577 . ? O1 Zn1 N1 87.55(8) . . ? N1 Zn1 N1 180.0 2_577 . ? O3 S1 O2 113.25(12) . . ? O3 S1 O1 110.89(12) . . ? O2 S1 O1 112.09(12) . . ? O3 S1 C2 109.10(13) . 1_556 ? O2 S1 C2 105.97(12) . 1_556 ? O1 S1 C2 105.05(12) . 1_556 ? S1 O1 Zn1 132.37(12) . . ? C3 N1 N2 105.1(2) . . ? C3 N1 Zn1 127.07(19) . . ? N2 N1 Zn1 127.38(18) . . ? C1 N2 N1 112.0(2) . . ? N2 C1 C2 107.0(2) . . ? C1 C2 C3 105.6(2) . . ? C1 C2 S1 126.1(2) . 1_554 ? C3 C2 S1 128.2(2) . 1_554 ? N1 C3 C2 110.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4B O2 0.811(18) 2.41(3) 2.961(3) 126(3) 1_564 O4 H4B O2 0.811(18) 2.26(2) 2.967(3) 147(3) 2_577 O4 H4A O3 0.808(18) 1.911(19) 2.715(3) 174(4) 2_677 N2 H2 O2 0.86 2.06 2.891(3) 160.8 1_564 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.309 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.120 #===END data_cadmiumpyrazolesulfonate _database_code_depnum_ccdc_archive 'CCDC 837808' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 Cd N4 O8 S2' _chemical_formula_weight 442.70 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6676(14) _cell_length_b 10.1917(16) _cell_length_c 7.5121(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.644(3) _cell_angle_gamma 90.00 _cell_volume 660.38(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 2.016 _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_reflns_number 2797 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 23.26 _reflns_number_total 949 _reflns_number_gt 894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0323P)^2^+0.4568P] 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 949 _refine_ls_number_parameters 103 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0209 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0517 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 1.0000 1.0000 1.0000 0.02382(15) Uani 1 2 d S . . S1 S 1.26242(8) 0.95957(7) 0.68312(9) 0.02271(19) Uani 1 1 d . . . O1 O 1.1114(2) 0.93424(19) 0.7478(2) 0.0295(5) Uani 1 1 d . . . O2 O 1.2798(2) 0.87678(19) 0.5266(3) 0.0321(5) Uani 1 1 d . . . O3 O 1.3901(2) 0.9488(2) 0.8201(3) 0.0364(5) Uani 1 1 d . . . O4 O 0.7979(3) 1.1127(2) 0.8423(3) 0.0372(5) Uani 1 1 d D . . H4A H 0.781(4) 1.110(4) 0.735(3) 0.045 Uiso 1 1 d D . . H4B H 0.771(4) 1.180(3) 0.884(5) 0.045 Uiso 1 1 d D . . C1 C 0.6247(3) 0.7117(3) 0.8754(5) 0.0377(8) Uani 1 1 d . . . H1 H 0.5203 0.6930 0.8459 0.045 Uiso 1 1 calc R . . C2 C 1.2549(3) 1.1241(3) 0.6175(4) 0.0234(6) Uani 1 1 d . . . C3 C 0.8763(3) 0.6981(3) 0.9343(4) 0.0280(6) Uani 1 1 d . . . H3 H 0.9764 0.6646 0.9514 0.034 Uiso 1 1 calc R . . N1 N 0.8397(3) 0.8229(2) 0.9562(3) 0.0259(5) Uani 1 1 d . . . N2 N 0.6857(3) 0.8285(2) 0.9187(3) 0.0341(6) Uani 1 1 d . . . H2 H 0.6324 0.8994 0.9223 0.041 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 Cd1 0.0265(2) 0.0176(2) 0.0272(2) -0.00252(10) 0.00194(14) -0.00283(10) S1 0.0267(4) 0.0165(4) 0.0247(4) 0.0001(3) 0.0015(3) 0.0031(3) O1 0.0343(11) 0.0241(12) 0.0313(10) -0.0021(8) 0.0098(9) -0.0041(8) O2 0.0415(12) 0.0254(11) 0.0307(10) -0.0026(9) 0.0096(9) 0.0053(9) O3 0.0354(12) 0.0298(12) 0.0414(12) 0.0029(10) -0.0089(10) 0.0073(10) O4 0.0491(14) 0.0310(13) 0.0302(11) -0.0018(10) -0.0030(10) 0.0130(10) C1 0.0215(16) 0.0273(17) 0.063(2) -0.0055(15) -0.0022(14) -0.0004(13) C2 0.0240(14) 0.0210(15) 0.0253(14) -0.0008(12) 0.0027(11) 0.0003(11) C3 0.0213(15) 0.0231(16) 0.0384(16) -0.0022(12) -0.0019(12) 0.0013(12) N1 0.0225(13) 0.0198(13) 0.0347(13) -0.0043(10) -0.0002(10) -0.0012(10) N2 0.0261(14) 0.0196(13) 0.0563(16) -0.0069(12) 0.0019(12) 0.0042(10) _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 Cd1 N1 2.282(2) 3_777 ? Cd1 N1 2.282(2) . ? Cd1 O1 2.3088(18) . ? Cd1 O1 2.3089(18) 3_777 ? Cd1 O4 2.320(2) 3_777 ? Cd1 O4 2.320(2) . ? S1 O3 1.439(2) . ? S1 O1 1.463(2) . ? S1 O2 1.467(2) . ? S1 C2 1.747(3) . ? C1 N2 1.330(4) . ? C1 C2 1.370(4) 2_746 ? C2 C1 1.370(4) 2_756 ? C2 C3 1.388(4) 2_756 ? C3 N1 1.325(4) . ? C3 C2 1.388(4) 2_746 ? N1 N2 1.338(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 N1 Cd1 N1 180.00(9) 3_777 . ? N1 Cd1 O1 92.88(7) 3_777 . ? N1 Cd1 O1 87.12(7) . . ? N1 Cd1 O1 87.12(7) 3_777 3_777 ? N1 Cd1 O1 92.88(7) . 3_777 ? O1 Cd1 O1 180.00(8) . 3_777 ? N1 Cd1 O4 84.23(8) 3_777 3_777 ? N1 Cd1 O4 95.77(8) . 3_777 ? O1 Cd1 O4 85.40(7) . 3_777 ? O1 Cd1 O4 94.60(7) 3_777 3_777 ? N1 Cd1 O4 95.77(8) 3_777 . ? N1 Cd1 O4 84.23(8) . . ? O1 Cd1 O4 94.60(7) . . ? O1 Cd1 O4 85.40(7) 3_777 . ? O4 Cd1 O4 180.000(1) 3_777 . ? O3 S1 O1 113.54(12) . . ? O3 S1 O2 113.38(13) . . ? O1 S1 O2 109.29(12) . . ? O3 S1 C2 106.21(13) . . ? O1 S1 C2 104.68(12) . . ? O2 S1 C2 109.26(12) . . ? S1 O1 Cd1 132.93(11) . . ? N2 C1 C2 106.9(3) . 2_746 ? C1 C2 C3 104.9(3) 2_756 2_756 ? C1 C2 S1 127.4(2) 2_756 . ? C3 C2 S1 127.4(2) 2_756 . ? N1 C3 C2 110.9(2) . 2_746 ? C3 N1 N2 105.1(2) . . ? C3 N1 Cd1 128.89(18) . . ? N2 N1 Cd1 125.25(17) . . ? C1 N2 N1 112.2(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O2 0.805(18) 1.989(19) 2.789(3) 173(4) 3_776 O4 H4B O2 0.797(19) 2.17(2) 2.966(3) 172(4) 2_756 N2 H2 O3 0.86 2.22 2.872(3) 132.3 1_455 N2 H2 O3 0.86 2.50 3.112(3) 128.8 3_777 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.273 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.074 #===END data_silverpyrazolesulfonate _database_code_depnum_ccdc_archive 'CCDC 837809' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H3 Ag N2 O3 S' _chemical_formula_weight 255.00 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5543(15) _cell_length_b 5.4219(10) _cell_length_c 14.260(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.590(4) _cell_angle_gamma 90.00 _cell_volume 584.04(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 3.743 _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_reflns_number 2438 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 23.23 _reflns_number_total 830 _reflns_number_gt 753 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0710P)^2^+0.3930P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.048(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 830 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Ag1 Ag 0.0000 0.0000 0.0000 0.0523(4) Uani 1 2 d S . . Ag2 Ag 0.5000 0.5000 0.5000 0.0461(4) Uani 1 2 d S . . S1 S 0.32094(11) -0.00085(13) 0.38899(6) 0.0252(4) Uani 1 1 d . . . O1 O 0.3479(3) -0.2660(5) 0.38411(15) 0.0373(7) Uani 1 1 d . . . O2 O 0.4851(3) 0.1369(4) 0.40375(16) 0.0342(7) Uani 1 1 d . . . O3 O 0.1828(3) 0.0676(6) 0.45365(18) 0.0436(7) Uani 1 1 d . . . N1 N 0.1340(4) 0.0715(6) 0.1312(2) 0.0307(7) Uani 1 1 d . . . N2 N 0.2178(3) 0.2878(5) 0.14532(18) 0.0319(7) Uani 1 1 d . . . H2 H 0.2235 0.4038 0.1044 0.038 Uiso 1 1 calc R . . C1 C 0.2914(4) 0.2996(6) 0.2312(2) 0.0296(8) Uani 1 1 d . . . H1 H 0.3569 0.4301 0.2558 0.036 Uiso 1 1 calc R . . C2 C 0.2518(4) 0.0828(7) 0.2761(2) 0.0233(7) Uani 1 1 d . . . C3 C 0.1532(4) -0.0538(7) 0.2104(3) 0.0280(8) Uani 1 1 d . . . H3 H 0.1076 -0.2106 0.2210 0.034 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 Ag1 0.0622(5) 0.0701(6) 0.0243(5) -0.00080(18) -0.0199(3) -0.0158(2) Ag2 0.0776(6) 0.0279(5) 0.0324(5) -0.00159(14) -0.0204(4) 0.00394(16) S1 0.0331(6) 0.0272(8) 0.0152(7) -0.0017(3) -0.0048(4) 0.0035(3) O1 0.0580(15) 0.0273(14) 0.0265(14) 0.0001(11) -0.0117(10) 0.0018(11) O2 0.0388(13) 0.0357(15) 0.0279(13) -0.0041(10) -0.0120(9) -0.0011(10) O3 0.0456(15) 0.0652(16) 0.0202(14) -0.0029(14) 0.0037(11) 0.0135(14) N1 0.0356(15) 0.0345(16) 0.0217(17) 0.0030(15) -0.0091(12) -0.0028(15) N2 0.0400(15) 0.0340(18) 0.0215(15) 0.0061(13) -0.0019(11) -0.0065(13) C1 0.0375(16) 0.0321(19) 0.0192(16) -0.0009(15) -0.0043(13) -0.0072(15) C2 0.0264(16) 0.0279(18) 0.0154(17) -0.0023(15) -0.0012(12) 0.0030(14) C3 0.0321(18) 0.0290(16) 0.0228(19) 0.0000(17) -0.0042(14) -0.0030(15) _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 Ag1 N1 2.154(3) . ? Ag1 N1 2.154(3) 3 ? Ag2 O1 2.371(2) 3_656 ? Ag2 O1 2.371(2) 1_565 ? Ag2 O2 2.402(2) . ? Ag2 O2 2.402(2) 3_666 ? S1 O3 1.448(3) . ? S1 O1 1.454(3) . ? S1 O2 1.461(2) . ? S1 C2 1.747(3) . ? O1 Ag2 2.371(2) 1_545 ? N1 C3 1.324(5) . ? N1 N2 1.346(4) . ? N2 C1 1.342(4) . ? C1 C2 1.373(5) . ? C2 C3 1.402(5) . ? 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 N1 Ag1 N1 180.0 . 3 ? O1 Ag2 O1 180.00(8) 3_656 1_565 ? O1 Ag2 O2 88.81(8) 3_656 . ? O1 Ag2 O2 91.19(8) 1_565 . ? O1 Ag2 O2 91.19(8) 3_656 3_666 ? O1 Ag2 O2 88.81(8) 1_565 3_666 ? O2 Ag2 O2 180.0 . 3_666 ? O3 S1 O1 112.70(18) . . ? O3 S1 O2 113.17(16) . . ? O1 S1 O2 113.17(15) . . ? O3 S1 C2 108.05(15) . . ? O1 S1 C2 104.67(16) . . ? O2 S1 C2 104.20(14) . . ? S1 O1 Ag2 124.25(13) . 1_545 ? S1 O2 Ag2 122.42(13) . . ? C3 N1 N2 105.8(3) . . ? C3 N1 Ag1 134.0(3) . . ? N2 N1 Ag1 120.2(2) . . ? C1 N2 N1 111.6(3) . . ? N2 C1 C2 107.1(3) . . ? C1 C2 C3 104.9(3) . . ? C1 C2 S1 126.0(3) . . ? C3 C2 S1 129.1(3) . . ? N1 C3 C2 110.6(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O3 0.86 2.17 2.853(4) 135.8 4_565 N2 H2 O2 0.86 2.54 3.024(4) 116.3 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.23 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.662 _refine_diff_density_min -1.003 _refine_diff_density_rms 0.195 #===END data_sodiumpyrazolesulfonate _database_code_depnum_ccdc_archive 'CCDC 837810' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H5 N2 Na O4 S' _chemical_formula_weight 188.14 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3639(15) _cell_length_b 7.1327(10) _cell_length_c 10.1111(15) _cell_angle_alpha 90.00 _cell_angle_beta 115.701(2) _cell_angle_gamma 90.00 _cell_volume 673.49(17) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.508 _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_reflns_number 3045 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 23.25 _reflns_number_total 965 _reflns_number_gt 880 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0446P)^2^+0.3004P] 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 0.186(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 965 _refine_ls_number_parameters 107 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0766 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 Na1 Na 0.50241(8) 0.48693(11) 0.26234(8) 0.0280(3) Uani 1 1 d . . . S1 S 0.32178(5) 0.23185(7) 0.41989(5) 0.0206(3) Uani 1 1 d . . . O1 O 0.31972(14) 0.4010(2) 0.33812(16) 0.0306(4) Uani 1 1 d . . . O2 O 0.41644(15) 0.25156(18) 0.57524(15) 0.0275(4) Uani 1 1 d . . . O3 O 0.34716(15) 0.0639(2) 0.35392(15) 0.0314(4) Uani 1 1 d . . . O4 O 0.34381(18) 0.7341(2) 0.08545(19) 0.0360(5) Uani 1 1 d D . . H4A H 0.255(2) 0.743(3) 0.060(3) 0.043 Uiso 1 1 d D . . H4B H 0.352(3) 0.709(4) 0.012(2) 0.043 Uiso 1 1 d D . . N1 N -0.0508(2) 0.2377(2) 0.4406(2) 0.0299(5) Uani 1 1 d . . . N2 N -0.07122(17) 0.1145(3) 0.33249(19) 0.0309(5) Uani 1 1 d . . . H2 H -0.1510 0.0576 0.2832 0.037 Uiso 1 1 calc R . . C1 C 0.0448(2) 0.0902(3) 0.3099(2) 0.0296(6) Uani 1 1 d . . . H1 H 0.0532 0.0114 0.2408 0.036 Uiso 1 1 calc R . . C2 C 0.1494(2) 0.2030(3) 0.4076(2) 0.0215(5) Uani 1 1 d . . . C3 C 0.0853(2) 0.2914(3) 0.4874(2) 0.0260(5) Uani 1 1 d . . . H3 H 0.1313 0.3765 0.5631 0.031 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 Na1 0.0276(5) 0.0266(5) 0.0331(5) -0.0019(3) 0.0164(4) -0.0035(3) S1 0.0171(4) 0.0230(4) 0.0230(4) 0.00105(18) 0.0098(3) 0.00127(18) O1 0.0222(7) 0.0342(9) 0.0373(8) 0.0123(7) 0.0146(7) 0.0023(6) O2 0.0231(9) 0.0300(9) 0.0256(8) -0.0003(6) 0.0071(7) -0.0008(6) O3 0.0287(8) 0.0342(9) 0.0359(9) -0.0064(7) 0.0184(7) 0.0028(7) O4 0.0272(9) 0.0461(11) 0.0362(9) -0.0026(7) 0.0152(8) -0.0018(7) N1 0.0247(10) 0.0338(11) 0.0352(11) 0.0030(8) 0.0168(9) 0.0017(7) N2 0.0213(9) 0.0346(11) 0.0344(10) -0.0026(8) 0.0100(8) -0.0079(8) C1 0.0296(12) 0.0316(13) 0.0317(12) -0.0077(9) 0.0171(10) -0.0073(9) C2 0.0204(11) 0.0221(10) 0.0239(10) 0.0023(8) 0.0113(9) 0.0006(8) C3 0.0245(11) 0.0287(12) 0.0270(11) -0.0016(9) 0.0134(9) 0.0000(9) _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 Na1 O2 2.3844(15) 3_666 ? Na1 O3 2.3881(15) 2_655 ? Na1 O2 2.4093(15) 4_565 ? Na1 O1 2.4096(15) . ? Na1 O4 2.4562(18) 2_645 ? Na1 O4 2.5415(19) . ? Na1 Na1 3.5739(5) 2_645 ? Na1 Na1 3.5739(5) 2_655 ? S1 O3 1.4497(15) . ? S1 O2 1.4536(15) . ? S1 O1 1.4575(15) . ? S1 C2 1.748(2) . ? O2 Na1 2.3844(15) 3_666 ? O2 Na1 2.4093(15) 4_566 ? O3 Na1 2.3882(15) 2_645 ? O4 Na1 2.4563(18) 2_655 ? N1 C3 1.334(3) . ? N1 N2 1.346(2) . ? N2 C1 1.329(3) . ? C1 C2 1.367(3) . ? C2 C3 1.399(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 O2 Na1 O3 92.79(6) 3_666 2_655 ? O2 Na1 O2 173.22(5) 3_666 4_565 ? O3 Na1 O2 82.75(6) 2_655 4_565 ? O2 Na1 O1 94.08(6) 3_666 . ? O3 Na1 O1 170.31(6) 2_655 . ? O2 Na1 O1 89.78(6) 4_565 . ? O2 Na1 O4 101.74(6) 3_666 2_645 ? O3 Na1 O4 95.30(6) 2_655 2_645 ? O2 Na1 O4 83.81(6) 4_565 2_645 ? O1 Na1 O4 89.99(6) . 2_645 ? O2 Na1 O4 82.49(5) 3_666 . ? O3 Na1 O4 81.67(6) 2_655 . ? O2 Na1 O4 91.78(6) 4_565 . ? O1 Na1 O4 92.45(6) . . ? O4 Na1 O4 174.96(5) 2_645 . ? O2 Na1 Na1 144.96(5) 3_666 2_645 ? O3 Na1 Na1 100.79(5) 2_655 2_645 ? O2 Na1 Na1 41.53(4) 4_565 2_645 ? O1 Na1 Na1 77.25(4) . 2_645 ? O4 Na1 Na1 45.31(4) 2_645 2_645 ? O4 Na1 Na1 131.14(5) . 2_645 ? O2 Na1 Na1 42.06(4) 3_666 2_655 ? O3 Na1 Na1 74.25(4) 2_655 2_655 ? O2 Na1 Na1 131.34(5) 4_565 2_655 ? O1 Na1 Na1 106.68(5) . 2_655 ? O4 Na1 Na1 139.64(6) 2_645 2_655 ? O4 Na1 Na1 43.40(4) . 2_655 ? Na1 Na1 Na1 172.54(5) 2_645 2_655 ? O3 S1 O2 113.89(8) . . ? O3 S1 O1 112.59(9) . . ? O2 S1 O1 111.71(8) . . ? O3 S1 C2 104.69(9) . . ? O2 S1 C2 106.15(9) . . ? O1 S1 C2 107.10(8) . . ? S1 O1 Na1 124.80(8) . . ? S1 O2 Na1 133.72(8) . 3_666 ? S1 O2 Na1 128.81(8) . 4_566 ? Na1 O2 Na1 96.41(5) 3_666 4_566 ? S1 O3 Na1 134.74(9) . 2_645 ? Na1 O4 Na1 91.29(6) 2_655 . ? C3 N1 N2 104.22(17) . . ? C1 N2 N1 112.91(16) . . ? N2 C1 C2 107.00(18) . . ? C1 C2 C3 104.80(18) . . ? C1 C2 S1 125.91(16) . . ? C3 C2 S1 129.24(16) . . ? N1 C3 C2 111.07(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A N1 0.843(18) 2.12(2) 2.933(3) 163(3) 2 O4 H4B O3 0.799(17) 2.51(2) 3.173(2) 142(3) 4_565 N2 H2 O1 0.86 1.99 2.842(2) 172.2 2_545 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.051 #===END data_ammoniumpyrazolesulfonate _database_code_depnum_ccdc_archive 'CCDC 837811' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H7 N3 O3 S' _chemical_formula_weight 165.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9194(17) _cell_length_b 7.2408(14) _cell_length_c 11.226(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.787(3) _cell_angle_gamma 90.00 _cell_volume 709.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.410 _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_reflns_number 3192 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 23.30 _reflns_number_total 1025 _reflns_number_gt 983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0390P)^2^+0.4648P] 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 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1025 _refine_ls_number_parameters 104 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.097 _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 0.21627(5) 0.21148(7) 0.38638(4) 0.0302(3) Uani 1 1 d . . . O1 O 0.21871(18) 0.1604(3) 0.51116(14) 0.0524(5) Uani 1 1 d . . . O2 O 0.11059(18) 0.3581(2) 0.34173(15) 0.0483(5) Uani 1 1 d . . . O3 O 0.19057(17) 0.0520(2) 0.30532(14) 0.0409(4) Uani 1 1 d . . . N1 N 0.6558(2) 0.3207(3) 0.42894(18) 0.0447(5) Uani 1 1 d . . . N2 N 0.5967(2) 0.4084(3) 0.32480(16) 0.0415(5) Uani 1 1 d . . . H2 H 0.6509 0.4683 0.2826 0.050 Uiso 1 1 calc R . . N3 N 0.9486(2) 0.2680(3) 0.59689(18) 0.0356(5) Uani 1 1 d D . . H1N H 1.030(2) 0.240(3) 0.569(2) 0.043 Uiso 1 1 d D . . H2N H 0.872(2) 0.283(3) 0.5315(18) 0.043 Uiso 1 1 d D . . H3N H 0.926(3) 0.179(3) 0.6432(19) 0.043 Uiso 1 1 d D . . H4N H 0.953(3) 0.376(3) 0.6338(19) 0.043 Uiso 1 1 d D . . C1 C 0.4450(2) 0.3928(3) 0.29363(19) 0.0401(6) Uani 1 1 d . . . H1 H 0.3819 0.4425 0.2249 0.048 Uiso 1 1 calc R . . C2 C 0.3999(2) 0.2897(3) 0.38213(18) 0.0292(5) Uani 1 1 d . . . C3 C 0.5357(3) 0.2491(3) 0.4641(2) 0.0412(6) Uani 1 1 d . . . H3 H 0.5410 0.1801 0.5347 0.049 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 0.0242(3) 0.0342(4) 0.0334(4) -0.0018(2) 0.0088(2) 0.0024(2) O1 0.0366(9) 0.0870(13) 0.0370(9) 0.0100(9) 0.0152(7) 0.0005(9) O2 0.0346(9) 0.0407(9) 0.0648(11) -0.0058(8) -0.0012(7) 0.0113(7) O3 0.0349(8) 0.0365(8) 0.0553(10) -0.0117(7) 0.0186(7) -0.0063(7) N1 0.0301(10) 0.0541(12) 0.0479(11) 0.0089(10) 0.0030(8) -0.0063(9) N2 0.0350(10) 0.0490(11) 0.0423(11) 0.0083(9) 0.0124(8) -0.0078(9) N3 0.0320(11) 0.0382(11) 0.0374(11) -0.0010(9) 0.0090(8) 0.0012(9) C1 0.0340(13) 0.0492(14) 0.0359(12) 0.0079(10) 0.0043(9) -0.0013(10) C2 0.0284(12) 0.0303(11) 0.0293(10) -0.0018(8) 0.0065(8) -0.0012(8) C3 0.0345(13) 0.0484(13) 0.0393(13) 0.0112(11) 0.0041(10) -0.0035(11) _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 O2 1.4403(16) . ? S1 O1 1.4448(16) . ? S1 O3 1.4588(15) . ? S1 C2 1.743(2) . ? N1 C3 1.321(3) . ? N1 N2 1.340(3) . ? N2 C1 1.331(3) . ? C1 C2 1.368(3) . ? C2 C3 1.395(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 O2 S1 O1 113.92(10) . . ? O2 S1 O3 110.98(10) . . ? O1 S1 O3 111.80(11) . . ? O2 S1 C2 107.63(10) . . ? O1 S1 C2 106.36(9) . . ? O3 S1 C2 105.60(9) . . ? C3 N1 N2 104.34(17) . . ? C1 N2 N1 112.76(17) . . ? N2 C1 C2 106.83(19) . . ? C1 C2 C3 104.44(19) . . ? C1 C2 S1 127.96(16) . . ? C3 C2 S1 127.44(16) . . ? N1 C3 C2 111.6(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O3 0.86 1.98 2.819(2) 165.7 2_655 N3 H1N O1 0.875(17) 2.005(17) 2.878(3) 176(2) 1_655 N3 H2N N1 0.903(16) 2.050(18) 2.917(3) 161(2) . N3 H3N O3 0.877(16) 2.112(18) 2.945(3) 158(2) 3_656 N3 H3N O2 0.877(16) 2.50(2) 2.976(3) 114.8(18) 4_666 N3 H4N O2 0.879(17) 2.044(18) 2.869(3) 156(2) 3_666 N3 H4N O3 0.879(17) 2.61(2) 3.125(3) 118.4(18) 4_666 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.226 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.045 #===END