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#$Date: 2022-11-23 10:49:42 +0200 (Wed, 23 Nov 2022) $
#$Revision: 279494 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106213.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_8106213
loop_
_publ_author_name
'Hong, Yong'
'Liu, Wei'
'Wu, Jie'
_publ_section_title
;
 Crystal structure of
 (E)-2,4-dichloro-6-(((4-methyl-2-nitrophenyl)imino)methyl)phenol,
 C14H10Cl2N2O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              549
_journal_page_last               550
_journal_paper_doi               10.1515/ncrs-2017-0280
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C14 H10 Cl2 N2 O3'
_chemical_formula_weight         325.14
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 96.739(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3172(15)
_cell_length_b                   7.0899(7)
_cell_length_c                   14.8280(15)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      3.00
_cell_volume                     1390.4(3)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18843
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         2.766
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8933.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0610P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2016
_reflns_number_total             2859
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0280_suppl.cif
_cod_data_source_block           111
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106213
_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   0.890
_shelx_estimated_absorpt_t_max   0.949
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
Cl1 Cl 0.34371(5) 0.36228(11) 0.56517(4) 0.0381(2) Uani 1 1 d . . . . .
Cl2 Cl 0.42453(5) 0.56064(11) 0.23080(4) 0.0356(2) Uani 1 1 d . . . . .
O1 O -0.05292(13) 0.3264(3) -0.04359(10) 0.0284(4) Uani 1 1 d . . . . .
O2 O 0.03087(13) 0.1932(3) 0.07315(11) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.20906(13) 0.5151(3) 0.18098(10) 0.0247(4) Uani 1 1 d . . . . .
H3 H 0.146320 0.500906 0.168748 0.053(10) Uiso 1 1 calc R . . . .
N1 N -0.03921(15) 0.2915(3) 0.03818(12) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.02508(14) 0.4337(3) 0.21460(12) 0.0168(4) Uani 1 1 d . . . . .
C1 C -0.11180(17) 0.3651(3) 0.09563(15) 0.0164(5) Uani 1 1 d . . . . .
C2 C -0.21170(17) 0.3729(3) 0.05815(15) 0.0190(5) Uani 1 1 d . . . . .
H2 H -0.229608 0.343129 -0.004122 0.023 Uiso 1 1 calc R U . . .
C3 C -0.28588(17) 0.4246(3) 0.11189(16) 0.0203(5) Uani 1 1 d . . . . .
C4 C -0.25552(18) 0.4690(3) 0.20284(16) 0.0218(5) Uani 1 1 d . . . . .
H4 H -0.305443 0.500340 0.241146 0.026 Uiso 1 1 calc R U . . .
C5 C -0.15495(17) 0.4686(3) 0.23857(15) 0.0190(5) Uani 1 1 d . . . . .
H5 H -0.136937 0.504614 0.300060 0.023 Uiso 1 1 calc R U . . .
C6 C -0.07927(17) 0.4162(3) 0.18575(14) 0.0159(5) Uani 1 1 d . . . . .
C7 C 0.05951(17) 0.3992(3) 0.29778(15) 0.0173(5) Uani 1 1 d . . . . .
H7 H 0.014775 0.357461 0.339055 0.021 Uiso 1 1 calc R U . . .
C8 C 0.16652(17) 0.4236(3) 0.32901(15) 0.0168(5) Uani 1 1 d . . . . .
C9 C 0.20039(18) 0.3877(3) 0.42055(15) 0.0196(5) Uani 1 1 d . . . . .
H9 H 0.153696 0.351960 0.461220 0.023 Uiso 1 1 calc R U . . .
C10 C 0.30149(19) 0.4044(3) 0.45111(15) 0.0225(5) Uani 1 1 d . . . . .
C11 C 0.37175(18) 0.4544(3) 0.39296(16) 0.0231(5) Uani 1 1 d . . . . .
H11 H 0.441590 0.463135 0.414728 0.028 Uiso 1 1 calc R U . . .
C12 C 0.33819(18) 0.4910(4) 0.30305(16) 0.0215(5) Uani 1 1 d . . . . .
C13 C 0.23617(17) 0.4769(3) 0.26902(15) 0.0184(5) Uani 1 1 d . . . . .
C14 C -0.39551(18) 0.4312(4) 0.07289(18) 0.0277(6) Uani 1 1 d . . . . .
H14A H -0.419095 0.562238 0.071002 0.042 Uiso 1 1 calc R U . . .
H14B H -0.435821 0.356504 0.111058 0.042 Uiso 1 1 calc R U . . .
H14C H -0.402915 0.379182 0.011234 0.042 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
O2 N1 O1 123.18(19) . .
O2 N1 C1 118.61(18) . .
O1 N1 C1 118.17(19) . .
C7 N2 C6 120.07(19) . .
C2 C1 C6 123.2(2) . .
C2 C1 N1 116.92(19) . .
C6 C1 N1 119.81(19) . .
C1 C2 C3 119.7(2) . .
C2 C3 C4 117.9(2) . .
C2 C3 C14 120.7(2) . .
C4 C3 C14 121.4(2) . .
C5 C4 C3 121.8(2) . .
C4 C5 C6 121.1(2) . .
C5 C6 C1 116.1(2) . .
C5 C6 N2 123.79(19) . .
C1 C6 N2 119.64(19) . .
N2 C7 C8 120.5(2) . .
C9 C8 C13 119.9(2) . .
C9 C8 C7 118.5(2) . .
C13 C8 C7 121.5(2) . .
C10 C9 C8 119.7(2) . .
C9 C10 C11 121.5(2) . .
C9 C10 Cl1 119.79(19) . .
C11 C10 Cl1 118.75(18) . .
C12 C11 C10 118.8(2) . .
C11 C12 C13 121.8(2) . .
C11 C12 Cl2 119.18(18) . .
C13 C12 Cl2 119.02(18) . .
O3 C13 C12 118.5(2) . .
O3 C13 C8 123.1(2) . .
C12 C13 C8 118.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C10 1.744(2) .
Cl2 C12 1.733(2) .
O1 N1 1.230(2) .
O2 N1 1.230(2) .
O3 C13 1.341(3) .
N1 C1 1.458(3) .
N2 C7 1.288(3) .
N2 C6 1.411(3) .
C1 C2 1.382(3) .
C1 C6 1.403(3) .
C2 C3 1.389(3) .
C3 C4 1.398(3) .
C3 C14 1.507(3) .
C4 C5 1.381(3) .
C5 C6 1.397(3) .
C7 C8 1.456(3) .
C8 C9 1.403(3) .
C8 C13 1.410(3) .
C9 C10 1.374(3) .
C10 C11 1.391(3) .
C11 C12 1.380(3) .
C12 C13 1.396(3) .
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
O3 H3 N2 0.84 1.89 2.621(3) 145.6 . 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
O2 N1 C1 C2 -142.7(2) . . . .
O1 N1 C1 C2 35.1(3) . . . .
O2 N1 C1 C6 34.6(3) . . . .
O1 N1 C1 C6 -147.6(2) . . . .
C6 C1 C2 C3 -3.3(4) . . . .
N1 C1 C2 C3 173.9(2) . . . .
C1 C2 C3 C4 0.7(3) . . . .
C1 C2 C3 C14 -179.0(2) . . . .
C2 C3 C4 C5 2.2(4) . . . .
C14 C3 C4 C5 -178.1(2) . . . .
C3 C4 C5 C6 -2.6(4) . . . .
C4 C5 C6 C1 0.1(3) . . . .
C4 C5 C6 N2 172.3(2) . . . .
C2 C1 C6 C5 2.9(3) . . . .
N1 C1 C6 C5 -174.2(2) . . . .
C2 C1 C6 N2 -169.7(2) . . . .
N1 C1 C6 N2 13.2(3) . . . .
C7 N2 C6 C5 38.1(3) . . . .
C7 N2 C6 C1 -149.9(2) . . . .
C6 N2 C7 C8 -177.7(2) . . . .
N2 C7 C8 C9 178.9(2) . . . .
N2 C7 C8 C13 -2.9(3) . . . .
C13 C8 C9 C10 -0.1(3) . . . .
C7 C8 C9 C10 178.1(2) . . . .
C8 C9 C10 C11 -0.7(4) . . . .
C8 C9 C10 Cl1 179.32(18) . . . .
C9 C10 C11 C12 1.2(4) . . . .
Cl1 C10 C11 C12 -178.86(19) . . . .
C10 C11 C12 C13 -0.8(4) . . . .
C10 C11 C12 Cl2 177.97(19) . . . .
C11 C12 C13 O3 179.8(2) . . . .
Cl2 C12 C13 O3 1.0(3) . . . .
C11 C12 C13 C8 0.0(4) . . . .
Cl2 C12 C13 C8 -178.80(18) . . . .
C9 C8 C13 O3 -179.4(2) . . . .
C7 C8 C13 O3 2.5(4) . . . .
C9 C8 C13 C12 0.5(3) . . . .
C7 C8 C13 C12 -177.7(2) . . . .
