#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/49/2214949.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_2214949
loop_
_publ_author_name
'Bai, Zheng-Chen'
'Jing, Zuo-Liang'
_publ_section_title
;
 (E)-N'-(2,4-Dichlorobenzylidene)thiophene-2-carbohydrazide
;
_journal_coeditor_code           AT2371
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3821
_journal_page_last               o3821
_journal_paper_doi               10.1107/S1600536807039694
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H8 Cl2 N2 O S'
_chemical_formula_moiety         'C12 H8 Cl2 N2 O S'
_chemical_formula_sum            'C12 H8 Cl2 N2 O S'
_chemical_formula_weight         299.16
_chemical_name_systematic
;
(E)-N'-(2,4-Dichlorobenzylidene)thiophene-2-carbohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6320(11)
_cell_length_b                   16.664(3)
_cell_length_c                   13.077(3)
_cell_measurement_reflns_used    2966
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.968
_cell_measurement_theta_min      1.897
_cell_volume                     1220.3(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2005)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9849
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_correction_T_min  0.9343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear, Rigaku/MSC, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0499
_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)+(0.0332P)²+0.3458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2370
_reflns_number_total             2911
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2371.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214949
_cod_database_fobs_code          2214949
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl1 1.20133(11) 0.60285(4) 0.68221(5) 0.02104(16) Uani d . 1
Cl Cl2 0.84737(12) 0.82985(4) 0.42176(4) 0.02250(17) Uani d . 1
S S1 0.16921(11) 0.87926(4) 0.83555(5) 0.02168(17) Uani d . 1
O O1 -0.1664(3) 1.00868(11) 0.60854(13) 0.0212(4) Uani d . 1
N N1 0.3309(4) 0.88243(13) 0.63613(15) 0.0168(5) Uani d . 1
N N2 0.1711(4) 0.94002(14) 0.59904(16) 0.0187(5) Uani d . 1
H H2 0.164(5) 0.956(2) 0.535(2) 0.042(9) Uiso d . 1
C C1 0.6565(4) 0.75502(16) 0.69296(18) 0.0186(5) Uani d . 1
H H1 0.5405 0.7671 0.7384 0.022 Uiso calc R 1
C C2 0.8196(4) 0.69461(16) 0.71835(18) 0.0189(6) Uani d . 1
H H2A 0.8139 0.6645 0.7797 0.023 Uiso calc R 1
C C3 0.9920(4) 0.67847(16) 0.65305(18) 0.0166(5) Uani d . 1
C C4 1.0012(4) 0.72071(16) 0.56257(18) 0.0175(5) Uani d . 1
H H4 1.1207 0.7094 0.5185 0.021 Uiso calc R 1
C C5 0.8331(4) 0.77977(16) 0.53762(17) 0.0164(5) Uani d . 1
C C6 0.6578(4) 0.79905(16) 0.60175(18) 0.0167(5) Uani d . 1
C C7 0.4807(4) 0.86188(16) 0.57394(18) 0.0173(5) Uani d . 1
H H7 0.4771 0.8877 0.5090 0.021 Uiso calc R 1
C C8 -0.0114(4) 0.96340(16) 0.65136(18) 0.0173(5) Uani d . 1
C C9 -0.0280(4) 0.93785(15) 0.75774(18) 0.0168(5) Uani d . 1
C C10 -0.2147(4) 0.96278(17) 0.80989(18) 0.0197(6) Uani d . 1
H H10 -0.3423 0.9953 0.7801 0.024 Uiso calc R 1
C C11 -0.1964(5) 0.93495(17) 0.91240(19) 0.0227(6) Uani d . 1
H H11 -0.3099 0.9465 0.9591 0.027 Uiso calc R 1
C C12 0.0027(5) 0.88965(17) 0.9365(2) 0.0238(6) Uani d . 1
H H12 0.0445 0.8664 1.0022 0.029 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
C12 S1 C9 91.51(13)
C7 N1 N2 114.6(2)
C8 N2 N1 122.0(2)
C8 N2 H2 116(2)
N1 N2 H2 121(2)
C2 C1 C6 121.6(2)
C2 C1 H1 119.2
C6 C1 H1 119.2
C1 C2 C3 119.1(2)
C1 C2 H2A 120.5
C3 C2 H2A 120.5
C4 C3 C2 121.4(2)
C4 C3 Cl1 118.03(19)
C2 C3 Cl1 120.56(19)
C5 C4 C3 118.6(2)
C5 C4 H4 120.7
C3 C4 H4 120.7
C4 C5 C6 122.1(2)
C4 C5 Cl2 116.99(19)
C6 C5 Cl2 120.9(2)
C5 C6 C1 117.2(2)
C5 C6 C7 121.4(2)
C1 C6 C7 121.4(2)
N1 C7 C6 120.7(2)
N1 C7 H7 119.6
C6 C7 H7 119.6
O1 C8 N2 118.9(2)
O1 C8 C9 119.4(2)
N2 C8 C9 121.7(2)
C10 C9 C8 120.7(2)
C10 C9 S1 110.85(18)
C8 C9 S1 128.38(19)
C9 C10 C11 112.9(2)
C9 C10 H10 123.6
C11 C10 H10 123.6
C12 C11 C10 112.1(2)
C12 C11 H11 123.9
C10 C11 H11 123.9
C11 C12 S1 112.6(2)
C11 C12 H12 123.7
S1 C12 H12 123.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.740(3)
Cl2 C5 1.739(2)
S1 C12 1.707(3)
S1 C9 1.727(3)
O1 C8 1.241(3)
N1 C7 1.279(3)
N1 N2 1.369(3)
N2 C8 1.351(3)
N2 H2 0.88(3)
C1 C2 1.379(4)
C1 C6 1.401(3)
C1 H1 0.9500
C2 C3 1.386(3)
C2 H2A 0.9500
C3 C4 1.383(3)
C4 C5 1.381(3)
C4 H4 0.9500
C5 C6 1.399(3)
C6 C7 1.465(4)
C7 H7 0.9500
C8 C9 1.467(3)
C9 C10 1.377(3)
C10 C11 1.412(3)
C10 H10 0.9500
C11 C12 1.361(4)
C11 H11 0.9500
C12 H12 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
N2 H2 O1 3_576 0.88(3) 1.96(3) 2.843(3) 177(3) 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
C7 N1 N2 C8 174.2(2)
C6 C1 C2 C3 1.5(4)
C1 C2 C3 C4 -1.0(4)
C1 C2 C3 Cl1 179.94(19)
C2 C3 C4 C5 -0.3(4)
Cl1 C3 C4 C5 178.72(18)
C3 C4 C5 C6 1.3(4)
C3 C4 C5 Cl2 -178.62(19)
C4 C5 C6 C1 -0.8(4)
Cl2 C5 C6 C1 179.06(19)
C4 C5 C6 C7 -180.0(2)
Cl2 C5 C6 C7 -0.1(3)
C2 C1 C6 C5 -0.6(4)
C2 C1 C6 C7 178.5(2)
N2 N1 C7 C6 -178.0(2)
C5 C6 C7 N1 -175.6(2)
C1 C6 C7 N1 5.4(4)
N1 N2 C8 O1 -171.5(2)
N1 N2 C8 C9 9.6(4)
O1 C8 C9 C10 0.8(4)
N2 C8 C9 C10 179.6(2)
O1 C8 C9 S1 -177.0(2)
N2 C8 C9 S1 1.9(4)
C12 S1 C9 C10 -0.6(2)
C12 S1 C9 C8 177.3(2)
C8 C9 C10 C11 -177.7(2)
S1 C9 C10 C11 0.4(3)
C9 C10 C11 C12 0.1(4)
C10 C11 C12 S1 -0.5(3)
C9 S1 C12 C11 0.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5263533
2 PubChem 6868775
