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#$Date: 2022-04-04 10:17:18 +0300 (Mon, 04 Apr 2022) $
#$Revision: 274297 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104997.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_8104997
loop_
_publ_author_name
'Li, Xia'
'Liu, Shangjun'
'Yan, Weihong'
'Shen, Mingle'
'Xue, Chaohui'
_publ_section_title
;
 Crystal structure of
 (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide,
 C8H8ClN3O4S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              5
_journal_page_last               6
_journal_paper_doi               10.1515/ncrs-2019-0410
_journal_volume                  235
_journal_year                    2019
_chemical_formula_moiety         'C8 H8 Cl N3 O S'
_chemical_formula_sum            'C8 H8 Cl N3 O S'
_chemical_formula_weight         229.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 94.103(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.662(2)
_cell_length_b                   5.2782(8)
_cell_length_c                   14.841(2)
_cell_measurement_reflns_used    1996
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.75
_cell_volume                     989.3(3)
_computing_cell_refinement       'APEX2-2008 [1]'
_computing_data_collection       'APEX2-2008 [1]'
_computing_data_reduction        'SAINT- 2008 [1]'
_computing_molecular_graphics    'SHELXTL [2]'
_computing_publication_material  'SHELXTL [2]'
_computing_structure_refinement  'SHELXL-2018/3 [2]'
_computing_structure_solution    'Bruker SHELXTL [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.612
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008 [1]'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.064
_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     128
_refine_ls_number_reflns         1745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0317
_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)+(0.0900P)²+0.0379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1494
_reflns_number_total             1745
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0410_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104997
_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   0.867
_shelx_estimated_absorpt_t_max   0.895
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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
C1 C 0.43980(15) -0.6564(4) 0.90319(13) 0.0247(5) Uani 1 1 d . . . . .
C2 C 0.29145(16) -0.1416(4) 0.81694(14) 0.0287(5) Uani 1 1 d . . . . .
H2 H 0.324296 -0.131957 0.762968 0.034 Uiso 1 1 calc R U . . .
C3 C 0.20683(15) 0.0370(4) 0.83323(14) 0.0289(5) Uani 1 1 d . . . . .
C4 C 0.15535(17) 0.0383(4) 0.91431(15) 0.0347(5) Uani 1 1 d . . . . .
C5 C 0.07628(19) 0.2148(5) 0.92830(19) 0.0452(6) Uani 1 1 d . . . . .
H5 H 0.043123 0.214548 0.982236 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0474(2) 0.3888(5) 0.8624(2) 0.0502(7) Uani 1 1 d . . . . .
H6 H -0.005719 0.505110 0.872205 0.060 Uiso 1 1 calc R U . . .
C7 C 0.0955(2) 0.3949(5) 0.7818(2) 0.0466(7) Uani 1 1 d . . . . .
H7 H 0.075263 0.513492 0.737565 0.056 Uiso 1 1 calc R U . . .
C8 C 0.17444(17) 0.2209(4) 0.76843(16) 0.0341(5) Uani 1 1 d . . . . .
Cl1 Cl 0.23532(6) 0.24002(15) 0.66736(5) 0.0590(3) Uani 1 1 d . . . . .
N1 N 0.39513(14) -0.6967(3) 0.97940(12) 0.0326(4) Uani 1 1 d . . . . .
H1A H 0.344512 -0.600273 0.994368 0.039 Uiso 1 1 calc R U . . .
H1B H 0.416592 -0.819409 1.014172 0.039 Uiso 1 1 calc R U . . .
N2 N 0.40402(13) -0.4624(3) 0.85054(11) 0.0294(4) Uani 1 1 d . . . . .
H2A H 0.432918 -0.432309 0.800937 0.035 Uiso 1 1 calc R U . . .
N3 N 0.32168(13) -0.3110(3) 0.87481(12) 0.0280(4) Uani 1 1 d . . . . .
O1 O 0.18019(14) -0.1282(3) 0.98182(12) 0.0487(5) Uani 1 1 d . . . . .
H1 H 0.230677 -0.214944 0.968897 0.073 Uiso 1 1 calc R U . . .
S1 S 0.54036(4) -0.83831(11) 0.86945(4) 0.0349(2) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 N2 118.26(17) . .
N1 C1 S1 122.61(16) . .
N2 C1 S1 119.13(15) . .
N3 C2 C3 121.86(19) . .
N3 C2 H2 119.1 . .
C3 C2 H2 119.1 . .
C8 C3 C4 116.77(19) . .
C8 C3 C2 120.92(19) . .
C4 C3 C2 122.30(19) . .
O1 C4 C5 117.1(2) . .
O1 C4 C3 122.14(19) . .
C5 C4 C3 120.8(2) . .
C6 C5 C4 119.9(2) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C5 C6 C7 121.4(2) . .
C5 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
C6 C7 C8 118.5(2) . .
C6 C7 H7 120.7 . .
C8 C7 H7 120.7 . .
C7 C8 C3 122.6(2) . .
C7 C8 Cl1 117.11(19) . .
C3 C8 Cl1 120.30(17) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C1 N2 N3 121.15(16) . .
C1 N2 H2A 119.4 . .
N3 N2 H2A 119.4 . .
C2 N3 N2 115.11(17) . .
C4 O1 H1 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.317(3) .
C1 N2 1.347(2) .
C1 S1 1.698(2) .
C2 N3 1.279(3) .
C2 C3 1.460(3) .
C2 H2 0.9300 .
C3 C8 1.407(3) .
C3 C4 1.409(3) .
C4 O1 1.353(3) .
C4 C5 1.394(3) .
C5 C6 1.372(4) .
C5 H5 0.9300 .
C6 C7 1.380(4) .
C6 H6 0.9300 .
C7 C8 1.382(3) .
C7 H7 0.9300 .
C8 Cl1 1.738(2) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N2 N3 1.382(2) .
N2 H2A 0.8600 .
O1 H1 0.8200 .
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
O1 H1 N3 0.82 1.94 2.659(2) 145.8 . yes
N2 H2A S1 0.86 2.62 3.4516(18) 162.3 2_656 yes
N1 H1B S1 0.86 2.53 3.3853(19) 172.0 3_637 yes
C2 H2 S1 0.93 2.91 3.756(2) 151.9 2_656 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
N3 C2 C3 C8 -179.66(19) . . . .
N3 C2 C3 C4 1.7(3) . . . .
C8 C3 C4 O1 -179.6(2) . . . .
C2 C3 C4 O1 -0.9(3) . . . .
C8 C3 C4 C5 0.1(3) . . . .
C2 C3 C4 C5 178.7(2) . . . .
O1 C4 C5 C6 -180.0(2) . . . .
C3 C4 C5 C6 0.4(4) . . . .
C4 C5 C6 C7 -0.4(4) . . . .
C5 C6 C7 C8 -0.1(4) . . . .
C6 C7 C8 C3 0.6(4) . . . .
C6 C7 C8 Cl1 -178.41(18) . . . .
C4 C3 C8 C7 -0.6(3) . . . .
C2 C3 C8 C7 -179.3(2) . . . .
C4 C3 C8 Cl1 178.41(15) . . . .
C2 C3 C8 Cl1 -0.3(3) . . . .
N1 C1 N2 N3 -0.9(3) . . . .
S1 C1 N2 N3 179.36(14) . . . .
C3 C2 N3 N2 -178.72(17) . . . .
C1 N2 N3 C2 -176.53(19) . . . .
