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#$Date: 2023-01-06 12:32:57 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280232 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106435.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_8106435
loop_
_publ_author_name
'El-Faham, Ayman'
'El-Merghany, Adel'
'Ghabbour, Hazem A.'
_publ_section_title
;
 Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide
 monohydrate, C13H14N2O3S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              69
_journal_page_last               71
_journal_paper_doi               10.1515/ncrs-2016-0152
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.600(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.9910(12)
_cell_length_b                   6.5721(3)
_cell_length_c                   14.2821(7)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.05
_cell_measurement_theta_min      2.86
_cell_volume                     2624.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus micro tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64167
_diffrn_reflns_theta_full        33.20
_diffrn_reflns_theta_max         33.20
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.8639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         5018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+2.3725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3921
_reflns_number_total             5018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0152_suppl.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8106435
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.446973(10) 0.51307(5) 0.40672(2) 0.01996(8) Uani 1 1 d . . .
O1 O 0.35067(3) 0.32976(13) 0.42592(6) 0.01678(17) Uani 1 1 d . . .
O2 O 0.25925(3) 0.53262(13) 0.27788(6) 0.01604(17) Uani 1 1 d . . .
N1 N 0.31011(3) 0.62900(15) 0.43446(7) 0.01299(18) Uani 1 1 d . . .
N2 N 0.26610(3) 0.53175(15) 0.43549(7) 0.01220(17) Uani 1 1 d . . .
C1 C 0.47559(4) 0.7261(2) 0.36984(10) 0.0244(3) Uani 1 1 d . . .
H1A H 0.5092 0.7341 0.3633 0.029 Uiso 1 1 calc R . .
C2 C 0.44483(4) 0.8840(2) 0.35081(10) 0.0223(3) Uani 1 1 d . . .
H2A H 0.4545 1.0133 0.3288 0.027 Uiso 1 1 calc R . .
C3 C 0.39675(4) 0.83209(18) 0.36783(9) 0.0166(2) Uani 1 1 d . . .
H3A H 0.3705 0.9229 0.3589 0.020 Uiso 1 1 calc R . .
C4 C 0.39258(4) 0.63457(17) 0.39874(8) 0.0130(2) Uani 1 1 d . . .
C5 C 0.34972(4) 0.51718(16) 0.42038(8) 0.01170(19) Uani 1 1 d . . .
C6 C 0.24225(4) 0.49004(16) 0.35350(8) 0.01168(19) Uani 1 1 d . . .
C7 C 0.19405(4) 0.39035(17) 0.36177(8) 0.0136(2) Uani 1 1 d . . .
H7A H 0.1942 0.3123 0.4211 0.016 Uiso 1 1 calc R . .
H7B H 0.1888 0.2928 0.3095 0.016 Uiso 1 1 calc R . .
C8 C 0.15280(4) 0.54074(17) 0.36007(7) 0.01192(19) Uani 1 1 d . . .
C9 C 0.10973(4) 0.48058(18) 0.39783(9) 0.0167(2) Uani 1 1 d . . .
H9A H 0.1073 0.3502 0.4259 0.020 Uiso 1 1 calc R . .
C10 C 0.07054(4) 0.6105(2) 0.39449(9) 0.0217(3) Uani 1 1 d . . .
H10A H 0.0414 0.5683 0.4199 0.026 Uiso 1 1 calc R . .
C11 C 0.07387(4) 0.8015(2) 0.35426(9) 0.0231(3) Uani 1 1 d . . .
H11A H 0.0469 0.8894 0.3513 0.028 Uiso 1 1 calc R . .
C12 C 0.11668(5) 0.8640(2) 0.31834(9) 0.0212(2) Uani 1 1 d . . .
H12A H 0.1192 0.9959 0.2918 0.025 Uiso 1 1 calc R . .
C13 C 0.15602(4) 0.73407(18) 0.32095(8) 0.0168(2) Uani 1 1 d . . .
H13A H 0.1852 0.7775 0.2959 0.020 Uiso 1 1 calc R . .
O1W O 0.21712(3) 0.53391(13) 0.10304(6) 0.01396(16) Uani 1 1 d . . .
H1N1 H 0.3082(6) 0.759(3) 0.4219(12) 0.028(4) Uiso 1 1 d . . .
H1N2 H 0.2553(6) 0.508(2) 0.4852(12) 0.016(4) Uiso 1 1 d . . .
H2OW H 0.2285(7) 0.530(3) 0.1580(15) 0.034(5) Uiso 1 1 d . . .
H1OW H 0.1988(7) 0.633(3) 0.0987(14) 0.036(5) Uiso 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
C1 S1 C4 91.43(6) . .
C5 N1 N2 119.01(9) . .
C5 N1 H1N1 122.8(11) . .
N2 N1 H1N1 114.0(11) . .
C6 N2 N1 119.25(9) . .
C6 N2 H1N2 122.8(12) . .
N1 N2 H1N2 117.9(12) . .
C2 C1 S1 112.54(9) . .
C2 C1 H1A 123.7 . .
S1 C1 H1A 123.7 . .
C1 C2 C3 112.14(11) . .
C1 C2 H2A 123.9 . .
C3 C2 H2A 123.9 . .
C4 C3 C2 112.07(10) . .
C4 C3 H3A 124.0 . .
C2 C3 H3A 124.0 . .
C3 C4 C5 130.02(10) . .
C3 C4 S1 111.81(8) . .
C5 C4 S1 118.10(8) . .
O1 C5 N1 123.23(10) . .
O1 C5 C4 121.42(10) . .
N1 C5 C4 115.35(10) . .
O2 C6 N2 121.26(10) . .
O2 C6 C7 123.33(10) . .
N2 C6 C7 115.41(9) . .
C6 C7 C8 113.44(9) . .
C6 C7 H7A 108.9 . .
C8 C7 H7A 108.9 . .
C6 C7 H7B 108.9 . .
C8 C7 H7B 108.9 . .
H7A C7 H7B 107.7 . .
C13 C8 C9 119.00(10) . .
C13 C8 C7 122.48(9) . .
C9 C8 C7 118.51(10) . .
C10 C9 C8 120.38(11) . .
C10 C9 H9A 119.8 . .
C8 C9 H9A 119.8 . .
C11 C10 C9 120.20(11) . .
C11 C10 H10A 119.9 . .
C9 C10 H10A 119.9 . .
C10 C11 C12 119.83(11) . .
C10 C11 H11A 120.1 . .
C12 C11 H11A 120.1 . .
C11 C12 C13 120.26(12) . .
C11 C12 H12A 119.9 . .
C13 C12 H12A 119.9 . .
C12 C13 C8 120.31(11) . .
C12 C13 H13A 119.8 . .
C8 C13 H13A 119.8 . .
H2OW O1W H1OW 107.8(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7083(13) .
S1 C4 1.7183(11) .
O1 C5 1.2345(13) .
O2 C6 1.2320(13) .
N1 C5 1.3528(14) .
N1 N2 1.3885(12) .
N1 H1N1 0.874(19) .
N2 C6 1.3495(14) .
N2 H1N2 0.799(16) .
C1 C2 1.3673(18) .
C1 H1A 0.9500 .
C2 C3 1.4201(16) .
C2 H2A 0.9500 .
C3 C4 1.3778(16) .
C3 H3A 0.9500 .
C4 C5 1.4711(15) .
C6 C7 1.5092(15) .
C7 C8 1.5192(15) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C13 1.3926(16) .
C8 C9 1.3998(15) .
C9 C10 1.3894(16) .
C9 H9A 0.9500 .
C10 C11 1.3853(19) .
C10 H10A 0.9500 .
C11 C12 1.3869(18) .
C11 H11A 0.9500 .
C12 C13 1.3926(16) .
C12 H12A 0.9500 .
C13 H13A 0.9500 .
O1W H2OW 0.83(2) .
O1W H1OW 0.83(2) .
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
C5 N1 N2 C6 -82.48(13) . . . .
C4 S1 C1 C2 -0.80(12) . . . .
S1 C1 C2 C3 0.87(16) . . . .
C1 C2 C3 C4 -0.48(17) . . . .
C2 C3 C4 C5 -177.00(12) . . . .
C2 C3 C4 S1 -0.12(14) . . . .
C1 S1 C4 C3 0.52(10) . . . .
C1 S1 C4 C5 177.80(10) . . . .
N2 N1 C5 O1 -14.20(16) . . . .
N2 N1 C5 C4 166.50(9) . . . .
C3 C4 C5 O1 162.56(12) . . . .
S1 C4 C5 O1 -14.15(15) . . . .
C3 C4 C5 N1 -18.13(17) . . . .
S1 C4 C5 N1 165.16(8) . . . .
N1 N2 C6 O2 1.59(16) . . . .
N1 N2 C6 C7 -178.09(9) . . . .
O2 C6 C7 C8 -85.75(13) . . . .
N2 C6 C7 C8 93.92(11) . . . .
C6 C7 C8 C13 22.43(15) . . . .
C6 C7 C8 C9 -158.76(10) . . . .
C13 C8 C9 C10 1.32(17) . . . .
C7 C8 C9 C10 -177.54(11) . . . .
C8 C9 C10 C11 -0.44(19) . . . .
C9 C10 C11 C12 -0.8(2) . . . .
C10 C11 C12 C13 1.2(2) . . . .
C11 C12 C13 C8 -0.34(19) . . . .
C9 C8 C13 C12 -0.93(17) . . . .
C7 C8 C13 C12 177.88(11) . . . .
