#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/09/2230922.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_2230922
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Faidallah, Hassan M.'
'Ng, Seik Weng'
_publ_section_title
;
 (E,E)-4-{4-[3-(4-Chloroanilino)-1-hydroxybut-2-enylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide
;
_journal_coeditor_code           XU5227
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1590
_journal_paper_doi               10.1107/S1600536811020617
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H19 Cl N4 O4 S'
_chemical_formula_moiety         'C20 H19 Cl N4 O4 S'
_chemical_formula_sum            'C20 H19 Cl N4 O4 S'
_chemical_formula_weight         446.90
_chemical_name_systematic
;
(E,E)-4-{4-[3-(4-Chloroanilino)-1-hydroxybut-2-enylidene]-
3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.496(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7513(17)
_cell_length_b                   17.545(2)
_cell_length_c                   7.6203(9)
_cell_measurement_reflns_used    656
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.13
_cell_measurement_theta_min      2.32
_cell_volume                     1932.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.099
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            32586
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Bruker, 2009)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.469
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0457P)²+2.8595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2605
_reflns_number_total             3426
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5227.cif
_cod_data_source_block           I
_cod_original_cell_volume        1932.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230922
_cod_database_fobs_code          2230922
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'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.06569(7) 0.72948(6) 1.73048(15) 0.0256(3) Uani d . 1 1 . .
S S1 0.14888(7) 0.47564(6) 0.00333(13) 0.0137(2) Uani d . 1 1 . .
O O1 0.58091(18) 0.59404(16) 1.0470(4) 0.0200(7) Uani d . 1 1 . .
H H1O 0.5745 0.5767 0.9424 0.030 Uiso calc R 1 1 . .
O O2 0.48625(17) 0.55620(16) 0.7504(4) 0.0187(6) Uani d . 1 1 . .
O O3 0.22069(18) 0.43897(16) -0.0680(4) 0.0194(7) Uani d . 1 1 . .
O O4 0.07052(18) 0.43097(15) 0.0288(4) 0.0169(6) Uani d . 1 1 . .
N N1 0.6886(2) 0.64430(18) 1.3466(4) 0.0147(7) Uani d . 1 1 . .
H H1 0.6866 0.6177 1.2480 0.018 Uiso calc R 1 1 . .
N N2 0.2764(2) 0.63178(18) 0.8250(4) 0.0129(7) Uani d . 1 1 . .
N N3 0.3294(2) 0.59328(17) 0.7196(4) 0.0115(7) Uani d . 1 1 . .
N N4 0.1079(2) 0.54401(18) -0.1294(4) 0.0158(7) Uani d . 1 1 . .
H H41 0.1513 0.5783 -0.1304 0.024 Uiso calc R 1 1 . .
H H42 0.0610 0.5652 -0.0922 0.024 Uiso calc R 1 1 . .
C C1 0.7783(3) 0.6666(2) 1.4438(5) 0.0181(9) Uani d . 1 1 . .
C C2 0.8495(3) 0.6126(2) 1.4652(5) 0.0195(9) Uani d . 1 1 . .
H H2 0.8370 0.5625 1.4200 0.023 Uiso calc R 1 1 . .
C C3 0.9374(3) 0.6319(2) 1.5512(5) 0.0200(9) Uani d . 1 1 . .
H H3 0.9860 0.5955 1.5648 0.024 Uiso calc R 1 1 . .
C C4 0.9541(3) 0.7048(2) 1.6175(5) 0.0187(9) Uani d . 1 1 . .
C C5 0.8863(3) 0.7590(2) 1.5964(5) 0.0214(10) Uani d . 1 1 . .
H H5 0.8998 0.8088 1.6429 0.026 Uiso calc R 1 1 . .
C C6 0.7972(3) 0.7406(2) 1.5065(6) 0.0205(9) Uani d . 1 1 . .
H H6 0.7499 0.7782 1.4880 0.025 Uiso calc R 1 1 . .
C C7 0.6074(3) 0.6606(2) 1.3933(5) 0.0140(9) Uani d . 1 1 . .
C C8 0.6086(3) 0.6938(2) 1.5746(5) 0.0218(10) Uani d . 1 1 . .
H H8A 0.6646 0.6771 1.6577 0.033 Uiso calc R 1 1 . .
H H8B 0.5539 0.6766 1.6182 0.033 Uiso calc R 1 1 . .
H H8C 0.6081 0.7496 1.5666 0.033 Uiso calc R 1 1 . .
C C9 0.5228(3) 0.6492(2) 1.2803(5) 0.0139(8) Uani d . 1 1 . .
H H9 0.4692 0.6617 1.3257 0.017 Uiso calc R 1 1 . .
C C10 0.5088(3) 0.6208(2) 1.1047(5) 0.0149(8) Uani d . 1 1 . .
C C11 0.2967(3) 0.6930(2) 1.1153(5) 0.0172(9) Uani d . 1 1 . .
H H11A 0.2318 0.7065 1.0700 0.026 Uiso calc R 1 1 . .
H H11B 0.3335 0.7397 1.1420 0.026 Uiso calc R 1 1 . .
H H11C 0.3018 0.6626 1.2246 0.026 Uiso calc R 1 1 . .
C C12 0.3320(3) 0.6480(2) 0.9771(5) 0.0118(8) Uani d . 1 1 . .
C C13 0.4237(3) 0.6199(2) 0.9796(5) 0.0141(8) Uani d . 1 1 . .
C C14 0.4195(3) 0.5859(2) 0.8100(5) 0.0133(8) Uani d . 1 1 . .
C C15 0.2875(2) 0.5682(2) 0.5466(5) 0.0113(8) Uani d . 1 1 . .
C C16 0.3375(3) 0.5229(2) 0.4485(5) 0.0148(8) Uani d . 1 1 . .
H H16 0.4003 0.5103 0.4957 0.018 Uiso calc R 1 1 . .
C C17 0.2940(3) 0.4966(2) 0.2817(5) 0.0149(8) Uani d . 1 1 . .
H H17 0.3275 0.4660 0.2137 0.018 Uiso calc R 1 1 . .
C C18 0.2025(3) 0.5143(2) 0.2129(5) 0.0136(8) Uani d . 1 1 . .
C C19 0.1535(3) 0.5618(2) 0.3080(5) 0.0154(9) Uani d . 1 1 . .
H H19 0.0913 0.5754 0.2589 0.018 Uiso calc R 1 1 . .
C C20 0.1966(3) 0.5890(2) 0.4746(5) 0.0134(8) Uani d . 1 1 . .
H H20 0.1641 0.6218 0.5397 0.016 Uiso calc R 1 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'
Cl Cl 0.1484 0.1585 '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
O3 S1 O4 . . 118.65(17) ?
O3 S1 N4 . . 108.04(17) ?
O4 S1 N4 . . 106.22(17) ?
O3 S1 C18 . . 106.40(17) ?
O4 S1 C18 . . 108.26(17) ?
N4 S1 C18 . . 109.02(17) ?
C10 O1 H1O . . 120.0 ?
C7 N1 C1 . . 125.6(3) ?
C7 N1 H1 . . 117.2 ?
C1 N1 H1 . . 117.2 ?
C12 N2 N3 . . 106.9(3) ?
C14 N3 N2 . . 110.6(3) ?
C14 N3 C15 . . 129.7(3) ?
N2 N3 C15 . . 119.8(3) ?
S1 N4 H41 . . 109.5 ?
S1 N4 H42 . . 109.5 ?
H41 N4 H42 . . 109.5 ?
C6 C1 C2 . . 119.7(4) ?
C6 C1 N1 . . 122.2(4) ?
C2 C1 N1 . . 118.0(4) ?
C3 C2 C1 . . 120.3(4) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 119.1(4) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C5 C4 C3 . . 121.9(4) ?
C5 C4 Cl1 . . 118.7(3) ?
C3 C4 Cl1 . . 119.4(3) ?
C4 C5 C6 . . 119.6(4) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C1 C6 C5 . . 119.3(4) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
N1 C7 C9 . . 123.0(4) ?
N1 C7 C8 . . 118.6(3) ?
C9 C7 C8 . . 118.3(3) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 C10 . . 126.0(4) ?
C7 C9 H9 . . 117.0 ?
C10 C9 H9 . . 117.0 ?
O1 C10 C9 . . 118.1(3) ?
O1 C10 C13 . . 116.0(3) ?
C9 C10 C13 . . 126.0(4) ?
C12 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C12 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N2 C12 C13 . . 111.0(3) ?
N2 C12 C11 . . 119.7(3) ?
C13 C12 C11 . . 129.2(3) ?
C14 C13 C10 . . 119.4(3) ?
C14 C13 C12 . . 105.3(3) ?
C10 C13 C12 . . 135.3(4) ?
O2 C14 N3 . . 126.7(3) ?
O2 C14 C13 . . 127.0(3) ?
N3 C14 C13 . . 106.2(3) ?
C20 C15 C16 . . 120.5(3) ?
C20 C15 N3 . . 119.6(3) ?
C16 C15 N3 . . 119.9(3) ?
C17 C16 C15 . . 118.9(4) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C18 C17 C16 . . 120.8(4) ?
C18 C17 H17 . . 119.6 ?
C16 C17 H17 . . 119.6 ?
C17 C18 C19 . . 120.3(3) ?
C17 C18 S1 . . 118.9(3) ?
C19 C18 S1 . . 120.8(3) ?
C20 C19 C18 . . 119.3(4) ?
C20 C19 H19 . . 120.3 ?
C18 C19 H19 . . 120.3 ?
C19 C20 C15 . . 120.0(4) ?
C19 C20 H20 . . 120.0 ?
C15 C20 H20 . . 120.0 ?
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
Cl1 C4 . 1.753(4) ?
S1 O3 . 1.436(3) ?
S1 O4 . 1.441(3) ?
S1 N4 . 1.607(3) ?
S1 C18 . 1.770(4) ?
O1 C10 . 1.316(5) ?
O1 H1O . 0.8400 ?
O2 C14 . 1.275(5) ?
N1 C7 . 1.346(5) ?
N1 C1 . 1.435(5) ?
N1 H1 . 0.8800 ?
N2 C12 . 1.310(5) ?
N2 N3 . 1.401(4) ?
N3 C14 . 1.376(5) ?
N3 C15 . 1.410(5) ?
N4 H41 . 0.8800 ?
N4 H42 . 0.8800 ?
C1 C6 . 1.393(6) ?
C1 C2 . 1.399(6) ?
C2 C3 . 1.374(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.379(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.365(6) ?
C5 C6 . 1.393(5) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C9 . 1.382(5) ?
C7 C8 . 1.497(5) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.404(5) ?
C9 H9 . 0.9500 ?
C10 C13 . 1.418(5) ?
C11 C12 . 1.491(5) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.435(5) ?
C13 C14 . 1.414(5) ?
C15 C20 . 1.392(5) ?
C15 C16 . 1.398(5) ?
C16 C17 . 1.383(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.382(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.397(5) ?
C19 C20 . 1.387(5) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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
O1 H1O O2 . 0.84 1.79 2.498(4) 141 yes
N1 H1 O1 . 0.88 2.00 2.659(4) 131 yes
N1 H1 O3 3_666 0.88 2.34 3.093(4) 143 yes
N4 H41 N2 1_554 0.88 2.16 3.003(4) 161 yes
N4 H42 O4 3_565 0.88 2.09 2.917(4) 156 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N2 N3 C14 . . . . 0.0(4) ?
C12 N2 N3 C15 . . . . 179.8(3) ?
C7 N1 C1 C6 . . . . -46.9(6) ?
C7 N1 C1 C2 . . . . 137.2(4) ?
C6 C1 C2 C3 . . . . 1.5(6) ?
N1 C1 C2 C3 . . . . 177.5(4) ?
C1 C2 C3 C4 . . . . 0.6(6) ?
C2 C3 C4 C5 . . . . -1.6(6) ?
C2 C3 C4 Cl1 . . . . 179.0(3) ?
C3 C4 C5 C6 . . . . 0.4(6) ?
Cl1 C4 C5 C6 . . . . 179.7(3) ?
C2 C1 C6 C5 . . . . -2.7(6) ?
N1 C1 C6 C5 . . . . -178.6(4) ?
C4 C5 C6 C1 . . . . 1.8(6) ?
C1 N1 C7 C9 . . . . 168.6(4) ?
C1 N1 C7 C8 . . . . -10.3(6) ?
N1 C7 C9 C10 . . . . -0.9(6) ?
C8 C7 C9 C10 . . . . 178.0(4) ?
C7 C9 C10 O1 . . . . 8.5(6) ?
C7 C9 C10 C13 . . . . -169.7(4) ?
N3 N2 C12 C13 . . . . -0.8(4) ?
N3 N2 C12 C11 . . . . 176.8(3) ?
O1 C10 C13 C14 . . . . 4.9(6) ?
C9 C10 C13 C14 . . . . -176.9(4) ?
O1 C10 C13 C12 . . . . -173.8(4) ?
C9 C10 C13 C12 . . . . 4.4(8) ?
N2 C12 C13 C14 . . . . 1.3(4) ?
C11 C12 C13 C14 . . . . -176.0(4) ?
N2 C12 C13 C10 . . . . -179.8(4) ?
C11 C12 C13 C10 . . . . 2.9(8) ?
N2 N3 C14 O2 . . . . -177.4(4) ?
C15 N3 C14 O2 . . . . 2.8(7) ?
N2 N3 C14 C13 . . . . 0.8(4) ?
C15 N3 C14 C13 . . . . -179.0(4) ?
C10 C13 C14 O2 . . . . -2.1(6) ?
C12 C13 C14 O2 . . . . 177.0(4) ?
C10 C13 C14 N3 . . . . 179.7(3) ?
C12 C13 C14 N3 . . . . -1.2(4) ?
C14 N3 C15 C20 . . . . -173.4(4) ?
N2 N3 C15 C20 . . . . 6.9(5) ?
C14 N3 C15 C16 . . . . 6.5(6) ?
N2 N3 C15 C16 . . . . -173.2(3) ?
C20 C15 C16 C17 . . . . -2.4(6) ?
N3 C15 C16 C17 . . . . 177.7(3) ?
C15 C16 C17 C18 . . . . -0.4(6) ?
C16 C17 C18 C19 . . . . 2.7(6) ?
C16 C17 C18 S1 . . . . -177.2(3) ?
O3 S1 C18 C17 . . . . -7.9(4) ?
O4 S1 C18 C17 . . . . 120.6(3) ?
N4 S1 C18 C17 . . . . -124.2(3) ?
O3 S1 C18 C19 . . . . 172.2(3) ?
O4 S1 C18 C19 . . . . -59.2(4) ?
N4 S1 C18 C19 . . . . 56.0(4) ?
C17 C18 C19 C20 . . . . -2.1(6) ?
S1 C18 C19 C20 . . . . 177.7(3) ?
C18 C19 C20 C15 . . . . -0.7(6) ?
C16 C15 C20 C19 . . . . 3.0(6) ?
N3 C15 C20 C19 . . . . -177.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656808
