#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/69/2006922.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2006922 loop_ _publ_author_name 'Elgemeie, Galal E.H.' 'Hanfy, Nadia' 'Hopf, Henning' 'Jones, Peter G.' _publ_section_title ; 5-Amino-1-phenylsulfonyl-4-pyrazolin-3-one ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 136 _journal_page_last 138 _journal_paper_doi 10.1107/S0108270197012420 _journal_volume 54 _journal_year 1998 _chemical_formula_sum 'C9 H9 N3 O3 S' _chemical_formula_weight 239.25 _chemical_name_systematic ; 5-Amino-1-phenylsulfonyl-pyrazolin-3-one ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 97.505(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.7794(10) _cell_length_b 7.8301(8) _cell_length_c 11.8317(12) _cell_measurement_reflns_used 57 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 4.5 _cell_volume 990.09(17) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Fait, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4442 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.13 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 297 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_meas ? _exptl_crystal_description tablet _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.358 _refine_diff_density_min -0.381 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.55(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.040 _refine_ls_goodness_of_fit_obs 1.108 _refine_ls_matrix_type full _refine_ls_number_parameters 314 _refine_ls_number_reflns 4235 _refine_ls_number_restraints 16 _refine_ls_restrained_S_all 1.039 _refine_ls_restrained_S_obs 1.107 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_obs .0328 _refine_ls_shift/esd_max -0.027 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0485P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0839 _refine_ls_wR_factor_obs .0810 _reflns_number_observed 3531 _reflns_number_total 4235 _reflns_observed_criterion >2sigma(I) _cod_data_source_file fg1382.cif _cod_data_source_block cheiro _cod_depositor_comments ; The following automatic conversions were performed: '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (22 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0485P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0485P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2006922 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 .0209(4) .0141(4) .0136(4) .0009(3) .0020(3) -.0004(3) N1 .0186(13) .0169(15) .0125(12) -.0005(11) .0050(10) -.0030(10) N2 .0220(14) .0177(16) .0125(13) -.0009(11) .0056(10) -.0016(11) N3 .0337(15) .0166(17) .0150(14) .0015(12) .0071(12) .0003(12) O1 .0251(11) .0218(14) .0209(11) -.0046(10) .0067(9) -.0074(10) O2 .0295(12) .0204(13) .0156(11) .0017(10) .0024(9) -.0041(9) O3 .0319(13) .0182(14) .0193(11) -.0014(10) .0077(10) .0042(9) C3 .0136(14) .0182(19) .0141(15) -.0026(12) .0017(11) -.0009(12) C4 .0163(14) .016(2) .0196(15) -.0019(13) .0032(12) .0021(14) C5 .0136(14) .0153(18) .0155(15) .0022(13) .0034(12) .0061(13) C11 .0214(15) .0170(19) .0182(16) .0024(13) .0004(13) .0037(12) C12 .0228(14) .060(2) .0241(14) .0070(15) .0023(11) .0013(15) C13 .0232(16) .088(4) .042(2) .0035(18) .0106(14) .004(2) C14 .0222(15) .050(3) .044(2) -.0018(15) -.0048(14) .0032(17) C15 .0291(14) .045(2) .0324(15) .0015(13) -.0079(11) -.0061(14) C16 .0274(13) .0381(18) .0209(13) .0008(12) .0014(10) -.0041(12) S1' .0189(4) .0138(4) .0158(4) -.0014(3) .0029(3) .0010(3) N1' .0204(13) .0114(14) .0114(12) -.0027(11) .0031(10) -.0009(10) N2' .0241(14) .0165(16) .0106(12) .0007(11) .0081(10) .0020(10) N3' .0305(14) .0199(18) .0137(13) -.0032(12) .0039(11) -.0020(12) O1' .0249(10) .0187(13) .0187(11) .0032(10) .0076(9) .0077(9) O2' .0262(11) .0205(14) .0182(11) -.0037(10) .0013(9) .0064(9) O3' .0295(13) .0169(13) .0256(13) .0014(10) .0047(10) -.0041(10) C5' .0131(14) .0194(18) .0166(16) .0003(13) .0012(12) .0003(14) C4' .0216(15) .0138(19) .0177(14) .0002(13) .0067(12) .0006(14) C3' .0155(14) .0145(19) .0210(16) .0009(12) .0009(12) .0038(12) C11' .0174(14) .018(2) .0246(18) -.0035(12) .0023(13) .0048(13) C12' .0242(13) .0223(17) .0315(14) .0004(12) .0036(11) -.0047(13) C13' .0248(15) .030(2) .050(2) .0059(13) .0075(13) .0003(15) C14' .0202(15) .041(2) .050(2) -.0032(14) -.0032(14) .0158(16) C15' .0322(15) .054(2) .0312(15) -.0135(15) -.0081(12) .0048(15) C16' .0300(14) .0368(19) .0213(12) -.0049(13) .0002(10) -.0010(12) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol S1 .30419(6) .47633(8) .95563(6) .01622(18) Uani d . 1 . S N1 .3889(2) .2944(3) .9579(2) .0157(6) Uani d . 1 . N N2 .3961(3) .2302(4) .8464(2) .0171(6) Uani d D 1 . N H2 .459(3) .269(5) .814(3) .047(13) Uiso d D 1 . H N3 .3422(3) .1770(4) 1.1333(2) .0214(6) Uani d D 1 . N H31 .335(3) .089(3) 1.175(2) .026(9) Uiso d D 1 . H H32 .369(3) .270(3) 1.162(2) .010(8) Uiso d D 1 . H O1 .4208(2) -.0359(3) .77081(19) .0223(5) Uani d . 1 . O O2 .3180(2) .5356(3) 1.07059(18) .0219(5) Uani d . 1 . O O3 .3489(2) .5778(3) .8691(2) .0228(5) Uani d . 1 . O C3 .3949(3) .0529(4) .8515(2) .0153(7) Uani d . 1 . C C4 .3636(3) .0074(4) .9619(3) .0173(7) Uani d . 1 . C H4 .3467 -.1045 .9868 .021 Uiso calc R 1 . H C5 .3623(3) .1522(4) 1.0241(3) .0147(6) Uani d . 1 . C C11 .1483(3) .4202(4) .9133(3) .0191(7) Uani d . 1 . C C12 .0643(3) .4266(5) .9920(3) .0358(8) Uani d . 1 . C H12 .0911 .4578 1.0689 .043 Uiso calc R 1 . H C13 -.0601(3) .3866(6) .9566(3) .0504(12) Uani d . 1 . C H13 -.1189 .3918 1.0097 .060 Uiso calc R 1 . H C14 -.0996(3) .3395(6) .8459(3) .0397(10) Uani d . 1 . C H14 -.1849 .3113 .8231 .048 Uiso calc R 1 . H C15 -.0152(3) .3333(4) .7677(3) .0367(7) Uani d . 1 . C H15 -.0426 .3007 .6912 .044 Uiso calc R 1 . H C16 .1086(3) .3742(4) .8003(2) .0290(6) Uani d . 1 . C H16 .1666 .3711 .7463 .035 Uiso calc R 1 . H S1' .30412(6) .36038(8) .45882(6) .01611(18) Uani d . 1 . S N1' .3858(2) .5434(3) .4551(2) .0143(5) Uani d . 1 . N N2' .3853(3) .6067(4) .3423(2) .0166(6) Uani d D 1 . N H2' .444(2) .556(4) .315(3) .024(9) Uiso d D 1 . H N3' .3549(3) .6615(4) .6348(2) .0213(6) Uani d D 1 . N H31' .371(3) .748(3) .680(2) .013(8) Uiso d D 1 . H H32' .377(4) .566(3) .668(3) .051(14) Uiso d D 1 . H O1' .4094(2) .8721(3) .26607(18) .0204(5) Uani d . 1 . O O2' .3180(2) .3122(3) .57661(18) .0218(5) Uani d . 1 . O O3' .3499(2) .2527(3) .3766(2) .0239(5) Uani d . 1 . O C5' .3667(3) .6864(4) .5252(3) .0164(7) Uani d . 1 . C C4' .3632(3) .8319(4) .4597(2) .0173(7) Uani d . 1 . C H4' .3480 .9447 .4841 .021 Uiso calc R 1 . H C3' .3863(3) .7829(4) .3496(3) .0172(7) Uani d . 1 . C C11' .1455(3) .4057(4) .4130(3) .0201(8) Uani d . 1 . C C12' .0780(3) .4956(4) .4862(2) .0260(6) Uani d . 1 . C H12' .1183 .5395 .5564 .031 Uiso calc R 1 . H C13' -.0493(3) .5198(4) .4546(3) .0349(8) Uani d . 1 . C H13' -.0969 .5823 .5027 .042 Uiso calc R 1 . H C14' -.1070(3) .4526(6) .3527(3) .0378(10) Uani d . 1 . C H14' -.1944 .4679 .3318 .045 Uiso calc R 1 . H C15' -.0388(3) .3637(5) .2815(3) .0400(8) Uani d . 1 . C H15' -.0795 .3178 .2120 .048 Uiso calc R 1 . H C16' .0889(3) .3409(4) .3104(2) .0296(6) Uani d . 1 . C H16' .1365 .2818 .2607 .036 Uiso calc R 1 . H 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O2 S1 O3 119.97(15) ? O2 S1 N1 105.69(13) ? O3 S1 N1 104.36(13) ? O2 S1 C11 109.40(15) ? O3 S1 C11 109.66(15) ? N1 S1 C11 106.85(15) ? C5 N1 N2 106.0(2) y C5 N1 S1 121.67(19) y N2 N1 S1 112.2(2) y C3 N2 N1 108.1(3) y O1 C3 N2 121.5(3) y O1 C3 C4 131.5(3) y N2 C3 C4 107.0(3) y C5 C4 C3 107.9(3) y N3 C5 C4 130.9(3) y N3 C5 N1 119.1(3) y C4 C5 N1 110.0(3) y C12 C11 C16 120.6(3) ? C12 C11 S1 119.2(2) ? C16 C11 S1 120.2(2) ? C11 C12 C13 118.7(3) ? C14 C13 C12 121.1(3) ? C13 C14 C15 119.9(3) ? C16 C15 C14 120.2(3) ? C15 C16 C11 119.5(3) ? O3' S1' O2' 120.48(15) ? O3' S1' N1' 104.89(13) ? O2' S1' N1' 105.11(13) ? O3' S1' C11' 108.57(16) ? O2' S1' C11' 109.06(15) ? N1' S1' C11' 108.05(15) ? N2' N1' C5' 106.8(2) y N2' N1' S1' 112.49(19) y C5' N1' S1' 122.5(2) y C3' N2' N1' 106.9(3) y N3' C5' C4' 132.1(3) y N3' C5' N1' 119.4(3) y C4' C5' N1' 108.6(3) y C5' C4' C3' 107.5(3) y O1' C3' N2' 120.3(3) y O1' C3' C4' 130.5(3) y N2' C3' C4' 109.2(3) y C16' C11' C12' 121.7(3) ? C16' C11' S1' 119.7(2) ? C12' C11' S1' 118.4(2) ? C13' C12' C11' 118.7(3) ? C14' C13' C12' 119.8(3) ? C15' C14' C13' 120.7(3) ? C14' C15' C16' 120.4(3) ? C11' C16' C15' 118.7(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O2 . 1.427(2) ? S1 O3 . 1.429(2) ? S1 N1 . 1.691(3) y S1 C11 . 1.746(3) ? N1 C5 . 1.412(4) y N1 N2 . 1.424(3) y N2 C3 . 1.389(4) y N3 C5 . 1.352(4) y O1 C3 . 1.242(4) y C3 C4 . 1.436(4) y C4 C5 . 1.353(5) y C11 C12 . 1.383(4) ? C11 C16 . 1.397(4) ? C12 C13 . 1.387(4) ? C13 C14 . 1.374(5) ? C14 C15 . 1.380(4) ? C15 C16 . 1.378(4) ? S1' O3' . 1.423(2) ? S1' O2' . 1.433(2) ? S1' N1' . 1.686(3) y S1' C11' . 1.762(3) ? N1' N2' . 1.423(3) y N1' C5' . 1.424(4) y N2' C3' . 1.382(4) y N3' C5' . 1.334(4) y O1' C3' . 1.262(4) y C5' C4' . 1.375(5) y C4' C3' . 1.411(4) y C11' C16' . 1.382(4) ? C11' C12' . 1.392(4) ? C12' C13' . 1.387(4) ? C13' C14' . 1.386(5) ? C14' C15' . 1.377(5) ? C15' C16' . 1.386(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O1' 2_646 0.87(2) 1.98(2) 2.852(3) 174(4) y N3 H31 O1' 1_546 0.86(2) 2.11(2) 2.897(4) 152(3) y N2' H2' O1 2_656 0.84(2) 2.02(2) 2.852(3) 171(3) y N3' H31' O1 1_565 0.87(2) 2.04(2) 2.900(4) 173(3) y N3 H32 O2 . 0.84(2) 2.37(3) 2.908(4) 122(2) y N3' H32' O2' . 0.86(2) 2.31(4) 2.836(4) 119(4) y 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_publ_flag O2 S1 N1 C5 59.9(3) ? O3 S1 N1 C5 -172.7(2) ? C11 S1 N1 C5 -56.6(3) ? O2 S1 N1 N2 -173.16(19) ? O3 S1 N1 N2 -45.8(2) ? C11 S1 N1 N2 70.4(2) ? C5 N1 N2 C3 -9.6(3) y S1 N1 N2 C3 -144.6(2) ? N1 N2 C3 O1 -167.9(3) ? N1 N2 C3 C4 10.5(3) y O1 C3 C4 C5 170.8(3) ? N2 C3 C4 C5 -7.5(4) y C3 C4 C5 N3 -177.7(3) ? C3 C4 C5 N1 1.4(3) y N2 N1 C5 N3 -175.8(3) ? S1 N1 C5 N3 -46.1(4) ? N2 N1 C5 C4 5.0(3) y S1 N1 C5 C4 134.6(2) ? O2 S1 C11 C12 -4.5(3) ? O3 S1 C11 C12 -138.0(3) ? N1 S1 C11 C12 109.5(3) y O2 S1 C11 C16 173.7(3) ? O3 S1 C11 C16 40.2(3) ? N1 S1 C11 C16 -72.4(3) ? C16 C11 C12 C13 0.0(5) ? S1 C11 C12 C13 178.1(3) ? C11 C12 C13 C14 0.7(6) ? C12 C13 C14 C15 -0.7(7) ? C13 C14 C15 C16 0.0(6) ? C14 C15 C16 C11 0.7(5) ? C12 C11 C16 C15 -0.6(5) ? S1 C11 C16 C15 -178.8(3) ? O3' S1' N1' N2' 50.0(2) ? O2' S1' N1' N2' 178.0(2) ? C11' S1' N1' N2' -65.7(2) ? O3' S1' N1' C5' 179.4(2) ? O2' S1' N1' C5' -52.6(3) ? C11' S1' N1' C5' 63.8(3) ? C5' N1' N2' C3' 9.2(3) y S1' N1' N2' C3' 146.3(2) ? N2' N1' C5' N3' 175.7(3) ? S1' N1' C5' N3' 43.9(4) ? N2' N1' C5' C4' -3.9(3) y S1' N1' C5' C4' -135.7(3) ? N3' C5' C4' C3' 177.7(3) ? N1' C5' C4' C3' -2.9(3) y N1' N2' C3' O1' 166.8(3) ? N1' N2' C3' C4' -11.1(4) y C5' C4' C3' O1' -168.8(3) ? C5' C4' C3' N2' 8.8(4) y O3' S1' C11' C16' -1.3(3) ? O2' S1' C11' C16' -134.3(3) ? N1' S1' C11' C16' 111.9(3) ? O3' S1' C11' C12' 173.7(2) ? O2' S1' C11' C12' 40.7(3) ? N1' S1' C11' C12' -73.0(3) y C16' C11' C12' C13' 0.1(5) ? S1' C11' C12' C13' -174.9(3) ? C11' C12' C13' C14' 1.0(5) ? C12' C13' C14' C15' -0.9(5) ? C13' C14' C15' C16' -0.3(6) ? C12' C11' C16' C15' -1.3(5) ? S1' C11' C16' C15' 173.6(2) ? C14' C15' C16' C11' 1.4(5) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 24729150 2 PubChem 139055853