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#$Date: 2022-11-24 10:37:58 +0200 (Thu, 24 Nov 2022) $
#$Revision: 279533 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106235.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_8106235
loop_
_publ_author_name
'Baashen, Mohammed'
'Abdel-Wahab, Bakr F.'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
'El-Hiti, Gamal A.'
_publ_section_title
;
 Crystal structure of
 1-phenyl-N′-(1-phenyl-5-(thiophen-2-yl)-1H-pyrazole-3-carbonyl)-5-(thiophen-2-yl)-1H-pyrazole-3-carbohydrazide,
 C28H20N6O2S2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              617
_journal_page_last               619
_journal_paper_doi               10.1515/ncrs-2017-0375
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C28 H20 N6 O2 S2'
_chemical_formula_sum            'C28 H20 N6 O2 S2'
_chemical_formula_weight         536.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                112.842(6)
_cell_angle_beta                 91.963(4)
_cell_angle_gamma                116.129(6)
_cell_formula_units_Z            2
_cell_length_a                   10.6738(6)
_cell_length_b                   11.7869(7)
_cell_length_c                   12.5381(7)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.2580
_cell_measurement_theta_min      4.9620
_cell_volume                     1264.38(17)
_computing_cell_refinement       'CrysAlis PRO [9]'
_computing_data_collection       'CrysAlis PRO [9]'
_computing_data_reduction        'CrysAlis PRO [9]'
_computing_molecular_graphics    'ORTEP-3 for Windows [12]'
_computing_publication_material  'WinGX [12] and CHEMDRAW Ultra [13]'
_computing_structure_refinement  'SHELXL [11]'
_computing_structure_solution    'SHELXS [10]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10719
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.680
_diffrn_reflns_theta_min         3.389
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       needle
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_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     417
_refine_ls_number_reflns         6002
_refine_ls_number_restraints     440
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0503P)²+0.5224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4380
_reflns_number_total             6002
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0375_suppl.cif
_cod_data_source_block           bmk1568
_cod_original_cell_volume        1264.38(15)
_cod_database_code               8106235
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.963
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.53465(11) 0.34985(13) 0.71518(12) 0.0664(4) Uani 0.768(3) 1 d D U P A 1
C1 C 0.4846(5) 0.4560(5) 0.8228(4) 0.0627(12) Uani 0.768(3) 1 d D U P A 1
H1 H 0.549379 0.537074 0.891002 0.075 Uiso 0.768(3) 1 calc R U P A 1
C2 C 0.3408(5) 0.4085(6) 0.7972(5) 0.0651(11) Uani 0.768(3) 1 d D U P A 1
H2 H 0.292964 0.450287 0.843816 0.078 Uiso 0.768(3) 1 calc R U P A 1
C3 C 0.2758(8) 0.2832(11) 0.6862(9) 0.0656(16) Uani 0.768(3) 1 d D U P A 1
H3 H 0.177161 0.234682 0.652859 0.079 Uiso 0.768(3) 1 calc R U P A 1
C4 C 0.3610(2) 0.2385(2) 0.63239(17) 0.0466(5) Uani 0.768(3) 1 d D U P A 1
S1A S 0.2424(7) 0.2796(10) 0.6921(9) 0.0688(14) Uani 0.232(3) 1 d D U P A 2
C1A C 0.3838(13) 0.4266(18) 0.8129(15) 0.057(3) Uani 0.232(3) 1 d D U P A 2
H1A H 0.369843 0.491069 0.875773 0.069 Uiso 0.232(3) 1 calc R U P A 2
C2A C 0.5156(14) 0.4382(16) 0.8067(13) 0.059(3) Uani 0.232(3) 1 d D U P A 2
H2A H 0.602666 0.507921 0.862585 0.070 Uiso 0.232(3) 1 calc R U P A 2
C3A C 0.4940(12) 0.3221(17) 0.6974(14) 0.067(3) Uani 0.232(3) 1 d D U P A 2
H3A H 0.569287 0.307032 0.674116 0.081 Uiso 0.232(3) 1 calc R U P A 2
C4A C 0.3610(2) 0.2385(2) 0.63239(17) 0.0466(5) Uani 0.232(3) 1 d D U P A 2
C5 C 0.3135(2) 0.10572(19) 0.52627(17) 0.0421(4) Uani 1 1 d . . . . .
C6 C 0.2007(2) -0.0253(2) 0.49954(18) 0.0473(5) Uani 1 1 d . . . . .
H6 H 0.134030 -0.048065 0.544076 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2068(2) -0.11664(19) 0.39219(18) 0.0447(4) Uani 1 1 d . . . . .
C8 C 0.5003(2) 0.19227(19) 0.41823(16) 0.0425(4) Uani 1 1 d . . . . .
C9 C 0.6187(3) 0.1766(3) 0.4017(2) 0.0677(7) Uani 1 1 d . . . . .
H9 H 0.621872 0.099208 0.402195 0.081 Uiso 1 1 calc R U . . .
C10 C 0.7305(3) 0.2750(4) 0.3846(3) 0.0898(9) Uani 1 1 d . . . . .
H10 H 0.811686 0.265428 0.373942 0.108 Uiso 1 1 calc R U . . .
C11 C 0.7275(3) 0.3892(3) 0.3826(2) 0.0809(9) Uani 1 1 d . . . . .
H11 H 0.806201 0.456831 0.371479 0.097 Uiso 1 1 calc R U . . .
C12 C 0.6079(3) 0.4026(2) 0.3970(2) 0.0694(7) Uani 1 1 d . . . . .
H12 H 0.604777 0.479025 0.394240 0.083 Uiso 1 1 calc R U . . .
C13 C 0.4937(2) 0.3062(2) 0.41518(18) 0.0508(5) Uani 1 1 d . . . . .
H13 H 0.412489 0.315899 0.425448 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1114(2) -0.2710(2) 0.32795(19) 0.0482(5) Uani 1 1 d . . . . .
C15 C 0.0942(2) -0.5481(2) 0.06679(19) 0.0493(5) Uani 1 1 d . . . . .
C16 C 0.0018(2) -0.70304(19) 0.00660(18) 0.0452(5) Uani 1 1 d . . . . .
C17 C 0.0174(2) -0.7993(2) -0.09108(18) 0.0478(5) Uani 1 1 d . . . . .
H17 H 0.085527 -0.779631 -0.135102 0.057 Uiso 1 1 calc R U . . .
C18 C -0.0892(2) -0.93014(19) -0.10910(16) 0.0421(4) Uani 1 1 d . . . . .
S2 S -0.1851(3) -1.21667(18) -0.1788(2) 0.0564(5) Uani 0.609(3) 1 d D U P B 1
C19 C -0.1175(2) -1.0688(2) -0.19663(17) 0.0440(4) Uani 0.609(3) 1 d D U P B 1
C20 C -0.0800(17) -1.0914(14) -0.3047(9) 0.057(2) Uani 0.609(3) 1 d D U P B 1
H20 H -0.042354 -1.022008 -0.330743 0.068 Uiso 0.609(3) 1 calc R U P B 1
C21 C -0.1048(12) -1.2311(7) -0.3716(8) 0.0511(13) Uani 0.609(3) 1 d D U P B 1
H21 H -0.087427 -1.264754 -0.446696 0.061 Uiso 0.609(3) 1 calc R U P B 1
C22 C -0.1571(10) -1.3091(8) -0.3113(5) 0.0500(13) Uani 0.609(3) 1 d D U P B 1
H22 H -0.175656 -1.401789 -0.338654 0.060 Uiso 0.609(3) 1 calc R U P B 1
S2A S -0.0696(7) -1.0881(6) -0.3229(4) 0.0560(8) Uani 0.391(3) 1 d D U P B 2
C19A C -0.1175(2) -1.0688(2) -0.19663(17) 0.0440(4) Uani 0.391(3) 1 d D U P B 2
C20A C -0.1586(18) -1.1886(11) -0.1788(14) 0.059(3) Uani 0.391(3) 1 d D U P B 2
H20A H -0.179414 -1.193369 -0.108754 0.071 Uiso 0.391(3) 1 calc R U P B 2
C21A C -0.1649(17) -1.3030(13) -0.2809(9) 0.056(2) Uani 0.391(3) 1 d D U P B 2
H21A H -0.200408 -1.394590 -0.289816 0.067 Uiso 0.391(3) 1 calc R U P B 2
C22A C -0.1120(19) -1.2596(10) -0.3630(12) 0.054(2) Uani 0.391(3) 1 d D U P B 2
H22A H -0.100014 -1.316450 -0.433204 0.064 Uiso 0.391(3) 1 calc R U P B 2
C23 C -0.2811(2) -1.00608(19) -0.00114(17) 0.0431(4) Uani 1 1 d . . . . .
C24 C -0.4113(2) -1.0925(2) -0.0840(2) 0.0565(6) Uani 1 1 d . . . . .
H24 H -0.423716 -1.086218 -0.154914 0.068 Uiso 1 1 calc R U . . .
C25 C -0.5238(3) -1.1892(2) -0.0603(2) 0.0696(7) Uani 1 1 d . . . . .
H25 H -0.613023 -1.247945 -0.115284 0.083 Uiso 1 1 calc R U . . .
C26 C -0.5048(3) -1.1988(3) 0.0434(3) 0.0768(8) Uani 1 1 d . . . . .
H26 H -0.580538 -1.264818 0.058451 0.092 Uiso 1 1 calc R U . . .
C27 C -0.3737(3) -1.1112(3) 0.1256(3) 0.0794(8) Uani 1 1 d . . . . .
H27 H -0.361020 -1.118217 0.196119 0.095 Uiso 1 1 calc R U . . .
C28 C -0.2615(3) -1.0134(3) 0.1042(2) 0.0625(6) Uani 1 1 d . . . . .
H28 H -0.173220 -0.952913 0.160305 0.075 Uiso 1 1 calc R U . . .
N1 N 0.38018(17) 0.08720(15) 0.43565(14) 0.0425(4) Uani 1 1 d . . . . .
N2 N 0.31608(18) -0.05003(16) 0.35200(15) 0.0463(4) Uani 1 1 d . . . . .
N3 N 0.14238(19) -0.33627(16) 0.22880(16) 0.0553(5) Uani 1 1 d . . . . .
H3B H 0.211634 -0.288734 0.204268 0.066 Uiso 1 1 calc R U . . .
N4 N 0.0618(2) -0.48181(17) 0.16540(17) 0.0599(5) Uani 1 1 d . . . . .
H4 H -0.008465 -0.529077 0.189308 0.072 Uiso 1 1 calc R U . . .
N5 N -0.10724(18) -0.76601(16) 0.04906(15) 0.0467(4) Uani 1 1 d . . . . .
N6 N -0.16261(17) -0.90569(15) -0.02352(14) 0.0435(4) Uani 1 1 d . . . . .
O1 O 0.01181(19) -0.33486(16) 0.36309(17) 0.0776(6) Uani 1 1 d . . . . .
O2 O 0.1941(2) -0.48422(16) 0.03243(17) 0.0810(6) Uani 1 1 d . . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C4 S1 C1 91.60(18) . .
C2 C1 S1 112.8(4) . .
C1 C2 C3 108.2(5) . .
C4 C3 C2 117.6(6) . .
C3 C4 C5 125.5(4) . .
C3 C4 S1 109.8(4) . .
C5 C4 S1 124.23(16) . .
C4A S1A C1A 88.9(5) . .
C2A C1A S1A 114.3(10) . .
C1A C2A C3A 106.5(11) . .
C4A C3A C2A 115.5(10) . .
C3A C4A C5 124.0(7) . .
C3A C4A S1A 114.7(6) . .
C5 C4A S1A 120.5(3) . .
N1 C5 C6 106.19(16) . .
N1 C5 C4 125.40(17) . .
C6 C5 C4 128.32(19) . .
N1 C5 C4A 125.40(17) . .
C6 C5 C4A 128.32(19) . .
C5 C6 C7 105.45(18) . .
N2 C7 C6 112.14(17) . .
N2 C7 C14 121.34(18) . .
C6 C7 C14 126.47(19) . .
C9 C8 C13 120.9(2) . .
C9 C8 N1 119.15(19) . .
C13 C8 N1 119.93(18) . .
C10 C9 C8 118.8(3) . .
C9 C10 C11 121.5(3) . .
C12 C11 C10 119.3(2) . .
C13 C12 C11 120.9(2) . .
C12 C13 C8 118.6(2) . .
O1 C14 N3 121.98(18) . .
O1 C14 C7 122.8(2) . .
N3 C14 C7 115.21(18) . .
O2 C15 N4 121.67(19) . .
O2 C15 C16 123.6(2) . .
N4 C15 C16 114.67(18) . .
N5 C16 C17 112.34(17) . .
N5 C16 C15 120.30(18) . .
C17 C16 C15 127.28(19) . .
C18 C17 C16 105.29(18) . .
N6 C18 C17 106.09(16) . .
N6 C18 C19 125.43(17) . .
C17 C18 C19 128.42(18) . .
N6 C18 C19A 125.43(17) . .
C17 C18 C19A 128.42(18) . .
C19 S2 C22 92.4(3) . .
C20 C19 C18 122.5(6) . .
C20 C19 S2 111.0(6) . .
C18 C19 S2 126.31(17) . .
C19 C20 C21 113.2(10) . .
C22 C21 C20 111.0(10) . .
C21 C22 S2 112.2(8) . .
C19A S2A C22A 92.7(6) . .
C20A C19A C18 126.9(6) . .
C20A C19A S2A 112.0(5) . .
C18 C19A S2A 120.0(3) . .
C19A C20A C21A 111.9(11) . .
C22A C21A C20A 110.5(13) . .
C21A C22A S2A 112.3(12) . .
C28 C23 C24 121.3(2) . .
C28 C23 N6 118.65(18) . .
C24 C23 N6 120.07(19) . .
C23 C24 C25 118.8(2) . .
C26 C25 C24 120.4(2) . .
C25 C26 C27 120.1(2) . .
C28 C27 C26 120.3(3) . .
C23 C28 C27 119.2(2) . .
N2 N1 C5 112.16(15) . .
N2 N1 C8 119.43(16) . .
C5 N1 C8 128.35(15) . .
C7 N2 N1 104.05(16) . .
C14 N3 N4 119.05(17) . .
C15 N4 N3 119.23(18) . .
C16 N5 N6 104.15(16) . .
N5 N6 C18 112.13(15) . .
N5 N6 C23 119.17(15) . .
C18 N6 C23 128.66(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.704(2) .
S1 C1 1.732(4) .
C1 C2 1.357(5) .
C2 C3 1.427(9) .
C3 C4 1.322(8) .
C4 C5 1.454(3) .
S1A C4A 1.650(6) .
S1A C1A 1.754(10) .
C1A C2A 1.360(9) .
C2A C3A 1.431(12) .
C3A C4A 1.309(10) .
C4A C5 1.454(3) .
C5 N1 1.358(2) .
C5 C6 1.371(3) .
C6 C7 1.385(3) .
C7 N2 1.331(3) .
C7 C14 1.473(3) .
C8 C9 1.367(3) .
C8 C13 1.390(3) .
C8 N1 1.434(2) .
C9 C10 1.344(4) .
C10 C11 1.370(4) .
C11 C12 1.363(4) .
C12 C13 1.353(3) .
C14 O1 1.215(2) .
C14 N3 1.325(3) .
C15 O2 1.211(3) .
C15 N4 1.333(3) .
C15 C16 1.473(3) .
C16 N5 1.333(2) .
C16 C17 1.385(3) .
C17 C18 1.375(3) .
C18 N6 1.366(2) .
C18 C19 1.455(3) .
C18 C19A 1.455(3) .
S2 C19 1.677(3) .
S2 C22 1.718(7) .
C19 C20 1.385(10) .
C20 C21 1.419(14) .
C21 C22 1.357(6) .
S2A C19A 1.643(4) .
S2A C22A 1.713(10) .
C19A C20A 1.393(11) .
C20A C21A 1.427(15) .
C21A C22A 1.355(8) .
C23 C28 1.371(3) .
C23 C24 1.372(3) .
C23 N6 1.429(2) .
C24 C25 1.383(3) .
C25 C26 1.364(4) .
C26 C27 1.374(4) .
C27 C28 1.372(3) .
N1 N2 1.358(2) .
N3 N4 1.382(2) .
N5 N6 1.353(2) .
