#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/71/2017129.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_2017129
loop_
_publ_author_name
'Kumarasinghe, Isuru R.'
'Hruby, Victor J.'
'Nichol, Gary S.'
_publ_section_title
;
 3-[1-(4-Sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl]propanoic
 acid and
 3-[5-(4-bromophenyl)-1-(4-sulfamoylphenyl)-1H-pyrazol-3-yl]propanoic
 acid--dichloromethane--diethyl ether--water (2/0.72/1/1)
;
_journal_coeditor_code           FN3023
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o296
_journal_page_last               o299
_journal_paper_doi               10.1107/S010827010901676X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H19 N3 O4 S'
_chemical_formula_moiety         'C19 H19 N3 O4 S'
_chemical_formula_sum            'C19 H19 N3 O4 S'
_chemical_formula_weight         385.43
_chemical_name_systematic
;3-[1-(4-Sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl]propanoic
 acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                106.928(3)
_cell_angle_beta                 97.777(3)
_cell_angle_gamma                101.077(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8382(14)
_cell_length_b                   12.582(3)
_cell_length_c                   13.279(3)
_cell_measurement_reflns_used    3944
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.75
_cell_volume                     896.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP3 for Windows (Farrugia, 1997) and Mercury (Version 2.2; Macrae
et al.,  2008)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6690
_diffrn_reflns_theta_full        25.53
_diffrn_reflns_theta_max         25.53
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.8977
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS Version 2008/1; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0648P)²+0.3322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                2824
_reflns_number_total             3300
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3023.cif
_cod_data_source_block           I
_cod_original_cell_volume        896.5(4)
_cod_database_code               2017129
_cod_database_fobs_code          2017129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 -0.48826(7) 0.25029(4) 0.42341(3) 0.01551(15) Uani d . 1 . .
O O1 -0.6249(2) 0.15155(11) 0.33376(10) 0.0221(3) Uani d . 1 . .
O O2 -0.6121(2) 0.32605(11) 0.48363(10) 0.0209(3) Uani d . 1 . .
O O3 0.8431(2) 1.01701(11) 0.38423(11) 0.0269(3) Uani d . 1 . .
O O4 1.1563(2) 0.94718(12) 0.34640(12) 0.0247(3) Uani d . 1 . .
H H4O 1.222(5) 1.021(3) 0.354(2) 0.054(8) Uiso d . 1 . .
N N1 0.2549(3) 0.63100(12) 0.27877(12) 0.0171(3) Uani d . 1 . .
N N2 0.1831(3) 0.51422(12) 0.23132(12) 0.0164(3) Uani d . 1 . .
N N3 -0.3459(3) 0.20193(15) 0.50397(13) 0.0191(4) Uani d . 1 . .
H H3A -0.286(4) 0.250(2) 0.563(2) 0.028(6) Uiso d . 1 . .
H H3B -0.278(4) 0.150(2) 0.475(2) 0.040(7) Uiso d . 1 . .
C C1 0.2966(3) 0.47763(16) 0.14826(14) 0.0175(4) Uani d . 1 . .
C C2 0.4473(3) 0.57394(16) 0.14405(15) 0.0195(4) Uani d . 1 . .
H H2 0.554(4) 0.5750(17) 0.0932(17) 0.021(5) Uiso d . 1 . .
C C3 0.4159(3) 0.66676(15) 0.22625(14) 0.0171(4) Uani d . 1 . .
C C4 0.0243(3) 0.45057(15) 0.27776(13) 0.0156(4) Uani d . 1 . .
C C5 0.0334(3) 0.33912(16) 0.27229(14) 0.0175(4) Uani d . 1 . .
H H5 0.149(3) 0.3030(16) 0.2403(16) 0.013(5) Uiso d . 1 . .
C C6 -0.1226(3) 0.27852(16) 0.31774(14) 0.0175(4) Uani d . 1 . .
H H6 -0.112(3) 0.2031(18) 0.3141(16) 0.018(5) Uiso d . 1 . .
C C7 -0.2840(3) 0.33043(15) 0.36936(14) 0.0154(4) Uani d . 1 . .
C C8 -0.2889(3) 0.44215(15) 0.37791(14) 0.0180(4) Uani d . 1 . .
H H8 -0.402(4) 0.4767(17) 0.4124(17) 0.019(5) Uiso d . 1 . .
C C9 -0.1349(3) 0.50225(16) 0.33127(14) 0.0180(4) Uani d . 1 . .
H H9 -0.143(3) 0.5755(18) 0.3359(16) 0.018(5) Uiso d . 1 . .
C C10 0.2531(3) 0.35711(15) 0.07841(14) 0.0168(4) Uani d . 1 . .
C C11 0.4297(3) 0.29761(17) 0.08549(15) 0.0214(4) Uani d . 1 . .
H H11 0.578(4) 0.334(2) 0.1343(19) 0.032(6) Uiso d . 1 . .
C C12 0.3909(4) 0.18445(17) 0.02208(15) 0.0225(4) Uani d . 1 . .
H H12 0.516(4) 0.142(2) 0.029(2) 0.041(7) Uiso d . 1 . .
C C13 0.1770(3) 0.12691(16) -0.05111(14) 0.0203(4) Uani d . 1 . .
C C14 0.0036(4) 0.18796(17) -0.06031(15) 0.0227(4) Uani d . 1 . .
H H14 -0.143(4) 0.151(2) -0.114(2) 0.034(6) Uiso d . 1 . .
C C15 0.0396(3) 0.30120(17) 0.00393(15) 0.0211(4) Uani d . 1 . .
H H15 -0.085(4) 0.3428(19) -0.0031(18) 0.027(6) Uiso d . 1 . .
C C16 0.5447(3) 0.79016(16) 0.25976(16) 0.0187(4) Uani d . 1 . .
H H16A 0.452(4) 0.8383(19) 0.3009(18) 0.028(6) Uiso d . 1 . .
H H16B 0.557(4) 0.8101(18) 0.1985(18) 0.024(6) Uiso d . 1 . .
C C17 0.7966(3) 0.81288(16) 0.32558(16) 0.0198(4) Uani d . 1 . .
H H17A 0.890(4) 0.7658(18) 0.2871(17) 0.020(5) Uiso d . 1 . .
H H17B 0.792(4) 0.7959(18) 0.3901(19) 0.026(6) Uiso d . 1 . .
C C18 0.9303(3) 0.93609(15) 0.35570(14) 0.0177(4) Uani d . 1 . .
C C19 0.1375(4) 0.00314(17) -0.11757(17) 0.0266(5) Uani d . 1 . .
H H19A 0.155(4) -0.042(2) -0.071(2) 0.035(6) Uiso d . 1 . .
H H19B 0.250(4) -0.008(2) -0.165(2) 0.038(7) Uiso d . 1 . .
H H19C -0.017(5) -0.027(2) -0.164(2) 0.054(8) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 118.72(8) ?
O1 S1 N3 . . 106.37(9) ?
O1 S1 C7 . . 105.96(8) ?
O2 S1 N3 . . 107.94(9) ?
O2 S1 C7 . . 108.10(8) ?
N3 S1 C7 . . 109.54(9) ?
H4O O4 C18 . . 109.3(18) ?
N2 N1 C3 . . 105.55(14) ?
N1 N2 C1 . . 111.17(14) ?
N1 N2 C4 . . 118.11(14) ?
C1 N2 C4 . . 130.52(15) ?
S1 N3 H3A . . 113.0(16) ?
S1 N3 H3B . . 116.1(17) ?
H3A N3 H3B . . 121(2) ?
N2 C1 C2 . . 106.25(16) ?
N2 C1 C10 . . 124.67(16) ?
C2 C1 C10 . . 129.06(17) ?
C1 C2 H2 . . 125.3(12) ?
C1 C2 C3 . . 106.23(17) ?
H2 C2 C3 . . 128.5(12) ?
N1 C3 C2 . . 110.79(16) ?
N1 C3 C16 . . 120.90(16) ?
C2 C3 C16 . . 128.24(17) ?
N2 C4 C5 . . 120.44(16) ?
N2 C4 C9 . . 119.17(16) ?
C5 C4 C9 . . 120.37(16) ?
C4 C5 H5 . . 122.3(12) ?
C4 C5 C6 . . 119.62(17) ?
H5 C5 C6 . . 118.0(12) ?
C5 C6 H6 . . 118.3(12) ?
C5 C6 C7 . . 119.45(17) ?
H6 C6 C7 . . 122.2(12) ?
S1 C7 C6 . . 118.87(14) ?
S1 C7 C8 . . 119.94(14) ?
C6 C7 C8 . . 121.18(16) ?
C7 C8 H8 . . 120.7(12) ?
C7 C8 C9 . . 119.33(17) ?
H8 C8 C9 . . 119.9(12) ?
C4 C9 C8 . . 120.00(17) ?
C4 C9 H9 . . 121.7(13) ?
C8 C9 H9 . . 118.3(13) ?
C1 C10 C11 . . 119.66(16) ?
C1 C10 C15 . . 121.67(17) ?
C11 C10 C15 . . 118.66(17) ?
C10 C11 H11 . . 120.2(14) ?
C10 C11 C12 . . 120.48(18) ?
H11 C11 C12 . . 119.3(14) ?
C11 C12 H12 . . 120.0(15) ?
C11 C12 C13 . . 121.46(18) ?
H12 C12 C13 . . 118.6(15) ?
C12 C13 C14 . . 117.82(17) ?
C12 C13 C19 . . 120.40(18) ?
C14 C13 C19 . . 121.78(18) ?
C13 C14 H14 . . 119.1(14) ?
C13 C14 C15 . . 121.17(18) ?
H14 C14 C15 . . 119.7(14) ?
C10 C15 C14 . . 120.36(18) ?
C10 C15 H15 . . 119.4(13) ?
C14 C15 H15 . . 120.2(13) ?
C3 C16 H16A . . 110.0(13) ?
C3 C16 H16B . . 108.4(13) ?
C3 C16 C17 . . 111.73(15) ?
H16A C16 H16B . . 107.5(18) ?
H16A C16 C17 . . 110.5(13) ?
H16B C16 C17 . . 108.6(13) ?
C16 C17 H17A . . 112.0(12) ?
C16 C17 H17B . . 111.4(14) ?
C16 C17 C18 . . 111.88(15) ?
H17A C17 H17B . . 106.2(18) ?
H17A C17 C18 . . 107.9(12) ?
H17B C17 C18 . . 107.2(13) ?
O3 C18 O4 . . 123.06(17) ?
O3 C18 C17 . . 124.42(17) ?
O4 C18 C17 . . 112.52(15) ?
C13 C19 H19A . . 110.1(14) ?
C13 C19 H19B . . 111.8(14) ?
C13 C19 H19C . . 112.4(16) ?
H19A C19 H19B . . 108(2) ?
H19A C19 H19C . . 109(2) ?
H19B C19 H19C . . 105(2) ?
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 O1 . 1.4485(13) ?
S1 O2 . 1.4313(13) ?
S1 N3 . 1.5931(17) ?
S1 C7 . 1.7735(18) ?
O3 C18 . 1.211(2) ?
O4 H4O . 0.90(3) ?
O4 C18 . 1.326(2) ?
N1 N2 . 1.373(2) ?
N1 C3 . 1.330(2) ?
N2 C1 . 1.374(2) ?
N2 C4 . 1.428(2) ?
N3 H3A . 0.82(3) ?
N3 H3B . 0.85(3) ?
C1 C2 . 1.374(3) ?
C1 C10 . 1.481(2) ?
C2 H2 . 0.98(2) ?
C2 C3 . 1.408(2) ?
C3 C16 . 1.494(3) ?
C4 C5 . 1.394(3) ?
C4 C9 . 1.390(3) ?
C5 H5 . 0.96(2) ?
C5 C6 . 1.387(3) ?
C6 H6 . 0.95(2) ?
C6 C7 . 1.391(3) ?
C7 C8 . 1.383(3) ?
C8 H8 . 0.95(2) ?
C8 C9 . 1.388(3) ?
C9 H9 . 0.92(2) ?
C10 C11 . 1.394(3) ?
C10 C15 . 1.397(3) ?
C11 H11 . 0.95(2) ?
C11 C12 . 1.383(3) ?
C12 H12 . 0.99(3) ?
C12 C13 . 1.394(3) ?
C13 C14 . 1.396(3) ?
C13 C19 . 1.505(3) ?
C14 H14 . 0.97(2) ?
C14 C15 . 1.389(3) ?
C15 H15 . 0.98(2) ?
C16 H16A . 0.98(2) ?
C16 H16B . 0.93(2) ?
C16 C17 . 1.534(3) ?
C17 H17A . 0.97(2) ?
C17 H17B . 0.94(2) ?
C17 C18 . 1.504(3) ?
C19 H19A . 0.96(3) ?
C19 H19B . 0.98(3) ?
C19 H19C . 0.96(3) ?
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
O4 H4O O1 1_765 0.90(3) 1.83(3) 2.705(2) 164(3) y
N3 H3A N1 2_566 0.82(3) 2.16(3) 2.941(2) 160(2) y
N3 H3B O3 1_445 0.85(3) 2.07(3) 2.910(2) 170(2) y
C8 H8 O2 2_466 0.95(2) 2.44(2) 3.167(2) 132.6(16) y
C16 H16A O4 1_455 0.98(2) 2.44(2) 3.387(2) 162.1(18) n
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C1 . . . . -0.96(19) ?
C3 N1 N2 C4 . . . . 174.50(15) ?
N1 N2 C1 C2 . . . . 0.9(2) ?
N1 N2 C1 C10 . . . . -177.90(16) ?
C4 N2 C1 C2 . . . . -173.84(17) ?
C4 N2 C1 C10 . . . . 7.4(3) ?
N2 C1 C2 C3 . . . . -0.5(2) ?
C10 C1 C2 C3 . . . . 178.26(18) ?
N2 N1 C3 C2 . . . . 0.6(2) ?
N2 N1 C3 C16 . . . . -176.73(15) ?
C1 C2 C3 N1 . . . . -0.1(2) ?
C1 C2 C3 C16 . . . . 177.01(18) ?
N1 N2 C4 C5 . . . . -148.48(16) ?
N1 N2 C4 C9 . . . . 29.7(2) ?
C1 N2 C4 C5 . . . . 25.9(3) ?
C1 N2 C4 C9 . . . . -155.91(18) ?
N2 C4 C5 C6 . . . . -179.90(15) ?
C9 C4 C5 C6 . . . . 2.0(3) ?
C4 C5 C6 C7 . . . . -0.8(3) ?
C5 C6 C7 S1 . . . . 178.08(13) ?
C5 C6 C7 C8 . . . . -1.2(3) ?
O1 S1 C7 C6 . . . . -59.09(16) ?
O1 S1 C7 C8 . . . . 120.17(15) ?
O2 S1 C7 C6 . . . . 172.65(13) ?
O2 S1 C7 C8 . . . . -8.09(17) ?
N3 S1 C7 C6 . . . . 55.27(16) ?
N3 S1 C7 C8 . . . . -125.47(15) ?
S1 C7 C8 C9 . . . . -177.27(13) ?
C6 C7 C8 C9 . . . . 2.0(3) ?
C7 C8 C9 C4 . . . . -0.8(3) ?
N2 C4 C9 C8 . . . . -179.32(15) ?
C5 C4 C9 C8 . . . . -1.2(3) ?
N2 C1 C10 C11 . . . . -110.9(2) ?
N2 C1 C10 C15 . . . . 69.9(2) ?
C2 C1 C10 C11 . . . . 70.6(3) ?
C2 C1 C10 C15 . . . . -108.6(2) ?
C1 C10 C11 C12 . . . . 179.00(17) ?
C15 C10 C11 C12 . . . . -1.8(3) ?
C10 C11 C12 C13 . . . . 0.6(3) ?
C11 C12 C13 C14 . . . . 1.4(3) ?
C11 C12 C13 C19 . . . . -178.80(18) ?
C12 C13 C14 C15 . . . . -2.2(3) ?
C19 C13 C14 C15 . . . . 177.99(18) ?
C13 C14 C15 C10 . . . . 1.0(3) ?
C1 C10 C15 C14 . . . . -179.82(17) ?
C11 C10 C15 C14 . . . . 1.0(3) ?
N1 C3 C16 C17 . . . . 100.8(2) ?
C2 C3 C16 C17 . . . . -76.0(2) ?
C3 C16 C17 C18 . . . . 177.72(16) ?
C16 C17 C18 O3 . . . . 40.4(3) ?
C16 C17 C18 O4 . . . . -138.85(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726444
2 PubChem 71148872
