#------------------------------------------------------------------------------
#$Date: 2022-04-04 11:26:27 +0300 (Mon, 04 Apr 2022) $
#$Revision: 274306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105005.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_8105005
loop_
_publ_author_name
'Song, Wei'
'Yang, Yanju'
_publ_section_title
;
 Crystal structure of
 (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              29
_journal_page_last               30
_journal_paper_doi               10.1515/ncrs-2019-0444
_journal_volume                  235
_journal_year                    2019
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11
_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                 97.849(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.039(6)
_cell_length_b                   4.0172(12)
_cell_length_c                   14.561(4)
_cell_measurement_reflns_used    1961
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.82
_cell_volume                     1219.1(6)
_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-2014/7  [2]'
_computing_structure_solution    'SHELXTL-2008 [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5658
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         0.977
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008 [1]'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0378
_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)+(0.0760P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1724
_reflns_number_total             2138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0444_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105005
_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   0.904
_shelx_estimated_absorpt_t_max   0.941
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 0.69103(10) 0.4769(6) 0.99961(16) 0.0444(5) Uani 1 1 d . . . . .
C2 C 0.63083(12) 0.5731(7) 0.95752(18) 0.0589(7) Uani 1 1 d . . . . .
H2 H 0.6213 0.5646 0.8933 0.071 Uiso 1 1 calc R U . . .
C3 C 0.58465(12) 0.6818(7) 1.0098(2) 0.0652(8) Uani 1 1 d . . . . .
H3 H 0.5443 0.7450 0.9809 0.078 Uiso 1 1 calc R U . . .
C4 C 0.59873(12) 0.6956(6) 1.10418(19) 0.0551(7) Uani 1 1 d . . . . .
C5 C 0.65817(13) 0.6081(7) 1.14736(18) 0.0644(7) Uani 1 1 d . . . . .
H5 H 0.6674 0.6226 1.2115 0.077 Uiso 1 1 calc R U . . .
C6 C 0.70437(12) 0.4985(7) 1.09604(17) 0.0584(7) Uani 1 1 d . . . . .
H6 H 0.7447 0.4386 1.1258 0.070 Uiso 1 1 calc R U . . .
C7 C 0.78474(10) 0.1915(5) 0.97360(15) 0.0392(5) Uani 1 1 d . . . . .
H7 H 0.7875 0.1106 1.0339 0.047 Uiso 1 1 calc R U . . .
C8 C 0.83479(10) 0.1059(5) 0.91790(13) 0.0354(5) Uani 1 1 d . . . . .
C9 C 0.83110(11) 0.2145(5) 0.82472(14) 0.0421(5) Uani 1 1 d . . . . .
C10 C 0.88006(13) 0.1395(6) 0.77278(15) 0.0500(6) Uani 1 1 d . . . . .
H10 H 0.8771 0.2115 0.7116 0.060 Uiso 1 1 calc R U . . .
C11 C 0.93244(12) -0.0390(6) 0.81080(16) 0.0505(6) Uani 1 1 d . . . . .
H11 H 0.9647 -0.0867 0.7751 0.061 Uiso 1 1 calc R U . . .
C12 C 0.93838(11) -0.1510(6) 0.90233(15) 0.0454(6) Uani 1 1 d . . . . .
H12 H 0.9742 -0.2712 0.9281 0.055 Uiso 1 1 calc R U . . .
C13 C 0.88961(10) -0.0782(5) 0.95331(13) 0.0363(5) Uani 1 1 d . . . . .
Cl1 Cl 0.54094(4) 0.8360(2) 1.17083(6) 0.0811(3) Uani 1 1 d . . . . .
Cl2 Cl 0.89754(3) -0.22329(15) 1.06773(4) 0.0481(2) Uani 1 1 d . . . . .
N1 N 0.73676(8) 0.3758(5) 0.94184(12) 0.0436(5) Uani 1 1 d . . . . .
O1 O 0.78048(9) 0.3933(5) 0.78446(10) 0.0592(5) Uani 1 1 d . . . . .
H1 H 0.7560 0.4300 0.8225 0.089 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C2 C1 C6 118.3(2) . .
C2 C1 N1 118.0(2) . .
C6 C1 N1 123.6(2) . .
C3 C2 C1 120.9(2) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C4 C3 C2 119.6(2) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C5 C4 C3 120.7(2) . .
C5 C4 Cl1 119.3(2) . .
C3 C4 Cl1 119.9(2) . .
C4 C5 C6 120.1(2) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 120.4(2) . .
C5 C6 H6 119.8 . .
C1 C6 H6 119.8 . .
N1 C7 C8 121.9(2) . .
N1 C7 H7 119.1 . .
C8 C7 H7 119.1 . .
C13 C8 C9 116.58(19) . .
C13 C8 C7 122.62(18) . .
C9 C8 C7 120.8(2) . .
O1 C9 C10 118.53(19) . .
O1 C9 C8 121.1(2) . .
C10 C9 C8 120.4(2) . .
C11 C10 C9 120.6(2) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C10 C11 C12 121.2(2) . .
C10 C11 H11 119.4 . .
C12 C11 H11 119.4 . .
C13 C12 C11 118.0(2) . .
C13 C12 H12 121.0 . .
C11 C12 H12 121.0 . .
C12 C13 C8 123.20(19) . .
C12 C13 Cl2 117.44(17) . .
C8 C13 Cl2 119.36(15) . .
C7 N1 C1 120.88(19) . .
C9 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 C2 1.385(3) .
C1 C6 1.396(3) .
C1 N1 1.421(3) .
C2 C3 1.384(4) .
C2 H2 0.9300 .
C3 C4 1.367(4) .
C3 H3 0.9300 .
C4 C5 1.367(4) .
C4 Cl1 1.749(3) .
C5 C6 1.377(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N1 1.286(3) .
C7 C8 1.455(3) .
C7 H7 0.9300 .
C8 C13 1.407(3) .
C8 C9 1.417(3) .
C9 O1 1.350(3) .
C9 C10 1.392(3) .
C10 C11 1.367(3) .
C10 H10 0.9300 .
C11 C12 1.396(3) .
C11 H11 0.9300 .
C12 C13 1.378(3) .
C12 H12 0.9300 .
C13 Cl2 1.751(2) .
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
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
C10 H10 Cl2 0.93 2.94 3.485(2) 118.5 4
O1 H1 N1 0.82 1.85 2.584(2) 148.4 .
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
C6 C1 C2 C3 -1.3(4) . . . .
N1 C1 C2 C3 -178.4(2) . . . .
C1 C2 C3 C4 0.3(4) . . . .
C2 C3 C4 C5 1.0(4) . . . .
C2 C3 C4 Cl1 179.4(2) . . . .
C3 C4 C5 C6 -1.2(4) . . . .
Cl1 C4 C5 C6 -179.7(2) . . . .
C4 C5 C6 C1 0.2(4) . . . .
C2 C1 C6 C5 1.0(4) . . . .
N1 C1 C6 C5 178.0(2) . . . .
N1 C7 C8 C13 176.0(2) . . . .
N1 C7 C8 C9 -2.2(3) . . . .
C13 C8 C9 O1 -179.87(18) . . . .
C7 C8 C9 O1 -1.6(3) . . . .
C13 C8 C9 C10 -0.1(3) . . . .
C7 C8 C9 C10 178.18(18) . . . .
O1 C9 C10 C11 179.6(2) . . . .
C8 C9 C10 C11 -0.2(3) . . . .
C9 C10 C11 C12 0.0(4) . . . .
C10 C11 C12 C13 0.4(3) . . . .
C11 C12 C13 C8 -0.7(3) . . . .
C11 C12 C13 Cl2 179.53(16) . . . .
C9 C8 C13 C12 0.6(3) . . . .
C7 C8 C13 C12 -177.68(19) . . . .
C9 C8 C13 Cl2 -179.67(15) . . . .
C7 C8 C13 Cl2 2.0(3) . . . .
C8 C7 N1 C1 -175.22(18) . . . .
C2 C1 N1 C7 -158.4(2) . . . .
C6 C1 N1 C7 24.6(4) . . . .
