#------------------------------------------------------------------------------
#$Date: 2023-03-01 11:21:42 +0200 (Wed, 01 Mar 2023) $
#$Revision: 281205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106791.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106791
loop_
_publ_author_name
'Aydın, Abdullah'
'Bilginer, Sinan'
'Gul, Halise Inci'
'Akkurt, Mehmet'
'Mete, Ebru'
_publ_section_title
;
 Crystal structure of
 4-[5-(4-fluorophenyl)-3-(4-hydroxyphenyl)-4,5-dihydropyrazol-1-yl]
 benzenesulfonamide, C21H18FN3O3S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              81
_journal_page_last               83
_journal_paper_doi               10.1515/ncrs-2015-0034
_journal_volume                  231
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety
;
C21 H18 F1 N3 O3 S1
;
_chemical_formula_sum            'C21 H18 F N3 O3 S'
_chemical_formula_weight         411.44
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 103.841(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6665(3)
_cell_length_b                   5.7483(2)
_cell_length_c                   14.7695(4)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.54
_cell_volume                     961.72(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear [18]'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEP-3 for Windows [20]'
_computing_publication_material  'PLATON [21]'
_computing_structure_refinement  'SHELXL-2014 [19]'
_computing_structure_solution    'SHELXS-2014 [19]'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23624
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details '[22], 1726 Friedel pairs'
_refine_ls_abs_structure_Flack   0.044(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4741
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0457P)²+0.1160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                4250
_reflns_number_total             4741
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            suppl_ncrs-2015-0034_Suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C21 H18 F1 N3 O3 S1'
_cod_database_code               8106791
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S Uani 0.98580(5) 1.00025(10) 0.35503(3) 1.000 0.0384(2) d . . .
F1 F Uani 0.29582(18) 0.7062(4) 0.55159(12) 1.000 0.0804(8) d . . .
O1 O Uani -0.05299(14) 1.0215(4) -0.20165(12) 1.000 0.0509(6) d . . .
O2 O Uani 1.04172(14) 0.9473(3) 0.28041(11) 1.000 0.0454(5) d . . .
O3 O Uani 1.02619(16) 0.8779(4) 0.44154(12) 1.000 0.0566(6) d . . .
N1 N Uani 0.42452(17) 0.8374(4) 0.11278(13) 1.000 0.0422(6) d . . .
N2 N Uani 0.49501(18) 0.7185(4) 0.18751(14) 1.000 0.0470(7) d . . .
N3 N Uani 1.0035(2) 1.2736(4) 0.37219(15) 1.000 0.0570(8) d . . .
C1 C Uani 0.2412(2) 1.0031(5) -0.04266(14) 1.000 0.0406(6) d . . .
C2 C Uani 0.1469(2) 1.0804(4) -0.11133(16) 1.000 0.0427(7) d . . .
C3 C Uani 0.0432(2) 0.9539(4) -0.13340(14) 1.000 0.0390(7) d . . .
C4 C Uani 0.0337(2) 0.7479(4) -0.08717(15) 1.000 0.0399(7) d . . .
C5 C Uani 0.1283(2) 0.6717(5) -0.01771(15) 1.000 0.0409(7) d . . .
C6 C Uani 0.2332(2) 0.7978(4) 0.00677(14) 1.000 0.0366(7) d . . .
C7 C Uani 0.3293(2) 0.7193(4) 0.08344(15) 1.000 0.0386(7) d . . .
C8 C Uani 0.3259(2) 0.4955(5) 0.13620(14) 1.000 0.0462(7) d . . .
C9 C Uani 0.4338(2) 0.5220(4) 0.21950(15) 1.000 0.0401(6) d . . .
C10 C Uani 0.39937(19) 0.5752(4) 0.30975(15) 1.000 0.0365(6) d . . .
C11 C Uani 0.3439(2) 0.7817(4) 0.32161(18) 1.000 0.0459(8) d . . .
C12 C Uani 0.3082(2) 0.8273(5) 0.40286(19) 1.000 0.0520(9) d . . .
C13 C Uani 0.3289(2) 0.6605(6) 0.47134(18) 1.000 0.0527(9) d . . .
C14 C Uani 0.3837(3) 0.4552(5) 0.46295(18) 1.000 0.0568(9) d . . .
C15 C Uani 0.4193(2) 0.4122(5) 0.38108(17) 1.000 0.0474(8) d . . .
C16 C Uani 0.6058(2) 0.7986(4) 0.23053(15) 1.000 0.0377(6) d . . .
C17 C Uani 0.6742(2) 0.6757(5) 0.30678(16) 1.000 0.0427(7) d . . .
C18 C Uani 0.7880(2) 0.7463(4) 0.34762(15) 1.000 0.0397(7) d . . .
C19 C Uani 0.83522(19) 0.9400(4) 0.31447(14) 1.000 0.0364(6) d . . .
C20 C Uani 0.7664(2) 1.0678(4) 0.24056(15) 1.000 0.0387(7) d . . .
C21 C Uani 0.65330(18) 0.9990(5) 0.19881(14) 1.000 0.0381(6) d . . .
H1 H Uiso 0.31090 1.08830 -0.02900 1.000 0.0490 c RU . .
H3BN H Uiso 0.99470 1.32870 0.42580 1.000 0.0680 d RU . .
H1O H Uiso -0.04070 1.17200 -0.22450 1.000 0.0760 d RU . .
H2 H Uiso 0.15310 1.21810 -0.14290 1.000 0.0510 c RU . .
H3AN H Uiso 1.02800 1.36000 0.32100 1.000 0.0680 d RU . .
H4 H Uiso -0.03560 0.66130 -0.10260 1.000 0.0480 c RU . .
H5 H Uiso 0.12170 0.53330 0.01320 1.000 0.0490 c RU . .
H8A H Uiso 0.33400 0.36110 0.09850 1.000 0.0550 c RU . .
H8B H Uiso 0.25330 0.48180 0.15690 1.000 0.0550 c RU . .
H9 H Uiso 0.48290 0.38190 0.22640 1.000 0.0480 c RU . .
H11 H Uiso 0.33030 0.89200 0.27420 1.000 0.0550 c RU . .
H12 H Uiso 0.27140 0.96680 0.41070 1.000 0.0620 c RU . .
H14 H Uiso 0.39710 0.34630 0.51090 1.000 0.0680 c RU . .
H15 H Uiso 0.45680 0.27290 0.37410 1.000 0.0570 c RU . .
H17 H Uiso 0.64270 0.54630 0.32990 1.000 0.0510 c RU . .
H18 H Uiso 0.83310 0.66310 0.39760 1.000 0.0480 c RU . .
H20 H Uiso 0.79750 1.20060 0.21950 1.000 0.0460 c RU . .
H21 H Uiso 0.60820 1.08490 0.14970 1.000 0.0460 c RU . .
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 117.70(11) . . . no
O2 S1 N3 105.32(11) . . . no
O2 S1 C19 107.31(10) . . . no
O3 S1 N3 109.77(12) . . . no
O3 S1 C19 107.26(11) . . . no
N3 S1 C19 109.28(12) . . . no
N2 N1 C7 107.9(2) . . . no
C3 O1 H1O 111.00 . . . no
N1 N2 C9 113.08(19) . . . no
N1 N2 C16 121.0(2) . . . no
C9 N2 C16 125.6(2) . . . no
C2 C1 C6 120.9(2) . . . no
C1 C2 C3 120.2(2) . . . no
O1 C3 C2 122.7(2) . . . no
C2 C3 C4 120.2(2) . . . no
S1 N3 H3AN 115.00 . . . no
O1 C3 C4 117.2(2) . . . no
S1 N3 H3BN 117.00 . . . no
H3BN N3 H3AN 128.00 . . . no
C3 C4 C5 119.5(2) . . . no
C4 C5 C6 121.5(2) . . . no
C5 C6 C7 120.3(2) . . . no
C1 C6 C7 121.9(2) . . . no
C1 C6 C5 117.8(2) . . . no
N1 C7 C8 113.8(2) . . . no
C6 C7 C8 123.6(2) . . . no
N1 C7 C6 122.6(2) . . . no
C7 C8 C9 102.1(2) . . . no
N2 C9 C8 100.69(18) . . . no
N2 C9 C10 112.27(19) . . . no
C8 C9 C10 112.62(19) . . . no
C9 C10 C11 121.1(2) . . . no
C11 C10 C15 118.8(2) . . . no
C9 C10 C15 120.1(2) . . . no
C10 C11 C12 121.2(2) . . . no
C11 C12 C13 118.0(3) . . . no
C12 C13 C14 122.8(2) . . . no
F1 C13 C12 118.2(3) . . . no
F1 C13 C14 119.0(3) . . . no
C13 C14 C15 118.5(3) . . . no
C10 C15 C14 120.6(2) . . . no
N2 C16 C21 121.5(2) . . . no
C17 C16 C21 119.0(2) . . . no
N2 C16 C17 119.5(2) . . . no
C16 C17 C18 120.3(2) . . . no
C17 C18 C19 120.3(2) . . . no
S1 C19 C18 119.38(17) . . . no
C18 C19 C20 119.8(2) . . . no
S1 C19 C20 120.34(17) . . . no
C19 C20 C21 120.6(2) . . . no
C16 C21 C20 119.9(2) . . . no
C2 C1 H1 120.00 . . . no
C6 C1 H1 120.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C7 C8 H8A 111.00 . . . no
C7 C8 H8B 111.00 . . . no
C9 C8 H8A 111.00 . . . no
C9 C8 H8B 111.00 . . . no
H8A C8 H8B 109.00 . . . no
N2 C9 H9 110.00 . . . no
C8 C9 H9 110.00 . . . no
C10 C9 H9 110.00 . . . no
C10 C11 H11 119.00 . . . no
C12 C11 H11 119.00 . . . no
C11 C12 H12 121.00 . . . no
C13 C12 H12 121.00 . . . no
C13 C14 H14 121.00 . . . no
C15 C14 H14 121.00 . . . no
C10 C15 H15 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C17 H17 120.00 . . . no
C18 C17 H17 120.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 120.00 . . . no
C19 C20 H20 120.00 . . . no
C21 C20 H20 120.00 . . . no
C16 C21 H21 120.00 . . . no
C20 C21 H21 120.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4411(17) . . no
S1 O3 1.4357(19) . . no
S1 N3 1.597(2) . . no
S1 C19 1.750(2) . . no
F1 C13 1.357(3) . . no
O1 C3 1.373(3) . . no
N1 N2 1.388(3) . . no
N1 C7 1.286(3) . . no
O1 H1O 0.9500 . . no
N2 C9 1.473(3) . . no
N2 C16 1.376(3) . . no
C1 C6 1.403(3) . . no
C1 C2 1.379(3) . . no
C2 C3 1.382(3) . . no
C3 C4 1.385(3) . . no
N3 H3BN 0.8800 . . no
N3 H3AN 1.0000 . . no
C4 C5 1.386(3) . . no
C5 C6 1.394(3) . . no
C6 C7 1.461(3) . . no
C7 C8 1.510(4) . . no
C8 C9 1.543(3) . . no
C9 C10 1.513(3) . . no
C10 C15 1.387(3) . . no
C10 C11 1.383(3) . . no
C11 C12 1.386(4) . . no
C12 C13 1.373(4) . . no
C13 C14 1.362(4) . . no
C14 C15 1.391(4) . . no
C16 C21 1.406(4) . . no
C16 C17 1.405(3) . . no
C17 C18 1.381(3) . . no
C18 C19 1.383(3) . . no
C19 C20 1.399(3) . . no
C20 C21 1.374(3) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C8 H8A 0.9700 . . no
C8 H8B 0.9700 . . no
C9 H9 0.9800 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15 0.9300 . . no
C17 H17 0.9300 . . no
C18 H18 0.9300 . . no
C20 H20 0.9300 . . no
C21 H21 0.9300 . . no
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
_geom_hbond_publ_flag
N3 H3BN O3 0.88 2.05 2.916(3) 167 2_756 yes
O1 H1O O2 0.95 1.78 2.727(3) 170 2_655 yes
N3 H3AN O1 1.00 2.07 3.067(3) 171 2_655 yes
C8 H8B O1 0.97 2.59 3.545(3) 170 2_545 yes
C18 H18 O3 0.93 2.51 2.894(3) 105 . yes
C2 H2 Cg4 0.93 2.83 3.559(3) 136 2_655 yes
C20 H20 Cg2 0.93 2.77 3.544(2) 141 2_655 yes
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
N3 S1 C19 C18 -139.07(18) . . . . no
O2 S1 C19 C20 -64.4(2) . . . . no
O3 S1 C19 C20 168.23(19) . . . . no
N3 S1 C19 C20 49.3(2) . . . . no
O2 S1 C19 C18 107.23(19) . . . . no
O3 S1 C19 C18 -20.1(2) . . . . no
C7 N1 N2 C9 -9.4(3) . . . . no
N2 N1 C7 C6 178.1(2) . . . . no
C7 N1 N2 C16 176.8(2) . . . . no
N2 N1 C7 C8 -1.2(3) . . . . no
N1 N2 C16 C21 -2.0(3) . . . . no
C9 N2 C16 C17 6.2(4) . . . . no
C9 N2 C16 C21 -175.0(2) . . . . no
N1 N2 C16 C17 179.2(2) . . . . no
N1 N2 C9 C8 15.0(2) . . . . no
C16 N2 C9 C8 -171.6(2) . . . . no
C16 N2 C9 C10 68.4(3) . . . . no
N1 N2 C9 C10 -105.0(2) . . . . no
C6 C1 C2 C3 -1.0(4) . . . . no
C2 C1 C6 C7 -176.4(2) . . . . no
C2 C1 C6 C5 1.8(3) . . . . no
C1 C2 C3 O1 -179.4(2) . . . . no
C1 C2 C3 C4 -0.5(3) . . . . no
O1 C3 C4 C5 180.0(2) . . . . no
C2 C3 C4 C5 1.0(3) . . . . no
C3 C4 C5 C6 -0.1(4) . . . . no
C4 C5 C6 C7 176.9(2) . . . . no
C4 C5 C6 C1 -1.3(3) . . . . no
C5 C6 C7 N1 -175.2(2) . . . . no
C1 C6 C7 C8 -177.8(2) . . . . no
C5 C6 C7 C8 4.0(3) . . . . no
C1 C6 C7 N1 3.0(4) . . . . no
C6 C7 C8 C9 -169.0(2) . . . . no
N1 C7 C8 C9 10.3(3) . . . . no
C7 C8 C9 C10 105.9(2) . . . . no
C7 C8 C9 N2 -13.9(2) . . . . no
C8 C9 C10 C15 112.3(3) . . . . no
C8 C9 C10 C11 -65.3(3) . . . . no
N2 C9 C10 C15 -134.9(2) . . . . no
N2 C9 C10 C11 47.5(3) . . . . no
C9 C10 C11 C12 177.5(2) . . . . no
C15 C10 C11 C12 -0.1(4) . . . . no
C9 C10 C15 C14 -177.4(2) . . . . no
C11 C10 C15 C14 0.3(4) . . . . no
C10 C11 C12 C13 -0.4(4) . . . . no
C11 C12 C13 C14 0.7(4) . . . . no
C11 C12 C13 F1 178.9(2) . . . . no
F1 C13 C14 C15 -178.8(3) . . . . no
C12 C13 C14 C15 -0.5(4) . . . . no
C13 C14 C15 C10 0.0(4) . . . . no
N2 C16 C21 C20 -176.9(2) . . . . no
N2 C16 C17 C18 176.5(2) . . . . no
C21 C16 C17 C18 -2.4(4) . . . . no
C17 C16 C21 C20 2.0(3) . . . . no
C16 C17 C18 C19 0.7(4) . . . . no
C17 C18 C19 C20 1.4(3) . . . . no
C17 C18 C19 S1 -170.28(18) . . . . no
S1 C19 C20 C21 169.79(18) . . . . no
C18 C19 C20 C21 -1.8(3) . . . . no
C19 C20 C21 C16 0.1(3) . . . . no
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{3edfcda7-041e-4e97-9ed6-01d30b375a0c} ? ? ?
{e59776cf-3000-4cc5-9d1c-9e1a165d0dd0} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{3edfcda7-041e-4e97-9ed6-01d30b375a0c} '_publcif_info_datablock.publ_exptl'
{e59776cf-3000-4cc5-9d1c-9e1a165d0dd0} '_geom_hbond_atom_site_label_D'
loop_
_publcif_info_cif.paper_type
CE
