#------------------------------------------------------------------------------
#$Date: 2023-01-19 10:58:41 +0200 (Thu, 19 Jan 2023) $
#$Revision: 280439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106498.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_8106498
loop_
_publ_author_name
'Yuan, Hua'
'Chen, Chunni'
'Wang, Linyan'
_publ_section_title
;
 Crystal structure of N-(3,4-dichlorobenzylidene)-4-methylaniline,
 C14H11Cl2N
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              249
_journal_page_last               250
_journal_paper_doi               10.1515/ncrs-2016-0225
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C14 H11 Cl2 N'
_chemical_formula_sum            'C14 H11 Cl2 N'
_chemical_formula_weight         264.14
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.055(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1494(3)
_cell_length_b                   14.4196(5)
_cell_length_c                   14.2686(8)
_cell_measurement_reflns_used    2205
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2230
_cell_measurement_theta_min      4.3600
_cell_volume                     1255.64(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6756
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         4.03
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  0.8546
_exptl_absorpt_correction_T_min  0.8091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0347
_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)+(0.0392P)²+0.2778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                2030
_reflns_number_total             2449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0225_suppl.cif
_cod_data_source_block           wly-2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106498
loop_
_symmetry_equiv_pos_as_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 0.43922(9) 0.73283(3) 0.63031(4) 0.06131(18) Uani 1 1 d . . . . .
Cl2 Cl 0.85709(8) 0.65646(3) 0.54576(4) 0.05815(17) Uani 1 1 d . . . . .
N1 N 0.8114(2) 0.29318(9) 0.62144(11) 0.0440(4) Uani 1 1 d . . . . .
C1 C 0.4957(3) 0.61516(11) 0.63048(12) 0.0413(4) Uani 1 1 d . . . . .
C2 C 0.6817(3) 0.58194(11) 0.59479(12) 0.0386(4) Uani 1 1 d . . . . .
C3 C 0.7262(3) 0.48821(11) 0.59714(12) 0.0392(4) Uani 1 1 d . . . . .
H3 H 0.8513 0.4661 0.5740 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5846(3) 0.42656(11) 0.63396(12) 0.0391(4) Uani 1 1 d . . . . .
C5 C 0.3978(3) 0.46060(13) 0.66749(13) 0.0466(4) Uani 1 1 d . . . . .
H5 H 0.3007 0.4196 0.6909 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3541(3) 0.55461(13) 0.66659(13) 0.0464(4) Uani 1 1 d . . . . .
H6 H 0.2298 0.5769 0.6902 0.056 Uiso 1 1 calc R U . . .
C7 C 0.6305(3) 0.32649(11) 0.63733(12) 0.0420(4) Uani 1 1 d . . . . .
H7 H 0.5213 0.2862 0.6518 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8433(3) 0.19551(11) 0.62316(12) 0.0391(4) Uani 1 1 d . . . . .
C9 C 0.6826(3) 0.13134(12) 0.59179(13) 0.0441(4) Uani 1 1 d . . . . .
H9 H 0.5426 0.1515 0.5687 0.053 Uiso 1 1 calc R U . . .
C10 C 0.7296(3) 0.03763(12) 0.59470(13) 0.0480(4) Uani 1 1 d . . . . .
H10 H 0.6190 -0.0044 0.5746 0.058 Uiso 1 1 calc R U . . .
C11 C 0.9372(3) 0.00453(12) 0.62673(12) 0.0447(4) Uani 1 1 d . . . . .
C12 C 1.0963(3) 0.06917(12) 0.65752(14) 0.0500(5) Uani 1 1 d . . . . .
H12 H 1.2366 0.0490 0.6801 0.060 Uiso 1 1 calc R U . . .
C13 C 1.0512(3) 0.16303(12) 0.65542(14) 0.0499(5) Uani 1 1 d . . . . .
H13 H 1.1617 0.2050 0.6759 0.060 Uiso 1 1 calc R U . . .
C14 C 0.9874(4) -0.09788(13) 0.62742(16) 0.0646(6) Uani 1 1 d . . . . .
H14A H 1.0628 -0.1150 0.6879 0.097 Uiso 1 1 calc R U . . .
H14B H 1.0784 -0.1115 0.5791 0.097 Uiso 1 1 calc R U . . .
H14C H 0.8532 -0.1323 0.6157 0.097 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'
N N 0.0061 0.0033 '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
C7 N1 C8 119.89(15) . .
C6 C1 C2 120.28(15) . .
C6 C1 Cl1 119.06(13) . .
C2 C1 Cl1 120.66(14) . .
C3 C2 C1 119.83(15) . .
C3 C2 Cl2 119.17(13) . .
C1 C2 Cl2 120.99(13) . .
C2 C3 C4 120.27(15) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 119.16(15) . .
C5 C4 C7 119.99(15) . .
C3 C4 C7 120.85(15) . .
C6 C5 C4 120.81(17) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C1 C6 C5 119.63(16) . .
C1 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
N1 C7 C4 122.66(16) . .
N1 C7 H7 118.7 . .
C4 C7 H7 118.7 . .
C13 C8 C9 118.24(16) . .
C13 C8 N1 117.38(16) . .
C9 C8 N1 124.34(16) . .
C10 C9 C8 120.31(17) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C11 121.84(17) . .
C9 C10 H10 119.1 . .
C11 C10 H10 119.1 . .
C12 C11 C10 117.34(16) . .
C12 C11 C14 121.40(18) . .
C10 C11 C14 121.26(18) . .
C13 C12 C11 121.40(17) . .
C13 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C12 C13 C8 120.86(17) . .
C12 C13 H13 119.6 . .
C8 C13 H13 119.6 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.7319(17) .
Cl2 C2 1.7298(17) .
N1 C7 1.258(2) .
N1 C8 1.422(2) .
C1 C6 1.377(2) .
C1 C2 1.393(2) .
C2 C3 1.378(2) .
C3 C4 1.392(2) .
C3 H3 0.9300 .
C4 C5 1.387(2) .
C4 C7 1.470(2) .
C5 C6 1.382(2) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C13 1.386(2) .
C8 C9 1.387(2) .
C9 C10 1.381(2) .
C9 H9 0.9300 .
C10 C11 1.386(3) .
C10 H10 0.9300 .
C11 C12 1.383(3) .
C11 C14 1.508(2) .
C12 C13 1.381(2) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
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 -1.1(3) . . . .
Cl1 C1 C2 C3 178.78(13) . . . .
C6 C1 C2 Cl2 177.96(14) . . . .
Cl1 C1 C2 Cl2 -2.1(2) . . . .
C1 C2 C3 C4 0.8(3) . . . .
Cl2 C2 C3 C4 -178.32(13) . . . .
C2 C3 C4 C5 0.5(3) . . . .
C2 C3 C4 C7 -179.70(16) . . . .
C3 C4 C5 C6 -1.5(3) . . . .
C7 C4 C5 C6 178.73(17) . . . .
C2 C1 C6 C5 0.2(3) . . . .
Cl1 C1 C6 C5 -179.73(15) . . . .
C4 C5 C6 C1 1.1(3) . . . .
C8 N1 C7 C4 -178.20(15) . . . .
C5 C4 C7 N1 -169.04(17) . . . .
C3 C4 C7 N1 11.2(3) . . . .
C7 N1 C8 C13 -146.26(18) . . . .
C7 N1 C8 C9 36.0(3) . . . .
C13 C8 C9 C10 1.2(3) . . . .
N1 C8 C9 C10 178.89(17) . . . .
C8 C9 C10 C11 -1.3(3) . . . .
C9 C10 C11 C12 1.1(3) . . . .
C9 C10 C11 C14 -178.58(17) . . . .
C10 C11 C12 C13 -0.7(3) . . . .
C14 C11 C12 C13 178.90(18) . . . .
C11 C12 C13 C8 0.7(3) . . . .
C9 C8 C13 C12 -0.9(3) . . . .
N1 C8 C13 C12 -178.74(16) . . . .
