#------------------------------------------------------------------------------
#$Date: 2023-12-14 11:37:38 +0200 (Thu, 14 Dec 2023) $
#$Revision: 288303 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/77/8107721.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_8107721
loop_
_publ_author_name
'Hong, Zhi'
'Chen, Guang'
'Jiang, Hua-Jiang'
'Chen, Ren-Er'
'Su, Wei-Ke'
_publ_section_title
;
 Crystal structure of α-(4-(hydroxyimino)-2,5-dichloro-2,5-cyclohexadien-
 1-ylidene)-benzeneacetonitrile, C14H8Cl2N2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              71
_journal_page_last               72
_journal_paper_doi               10.1515/ncrs-2014-9033
_journal_volume                  230
_journal_year                    2015
_chemical_formula_sum            'C14 H8 Cl2 N2 O'
_chemical_formula_weight         291.12
_chemical_name_common
;
alpha-(4-(hydroxyimino)-2,5-dichloro-2,5-cyclohexadien-
1-ylidene)-benzeneacetonitrile
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.
_cell_angle_beta                 106.875(3)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   18.692(4)
_cell_length_b                   5.8557(13)
_cell_length_c                   12.575(3)
_cell_volume                     1317.1(5)
_diffrn_ambient_temperature      296
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.484
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             592
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2175
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.1127
_cod_data_source_file            Z-2015-071.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107721
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl Uani 0.83904(3) -0.37152(9) 0.78467(5) 1.000 0.0621(2) . . . .
Cl2 Cl Uani 0.84366(3) 0.38170(10) 1.13808(5) 1.000 0.0649(2) . . . .
O1 O Uani 1.00565(8) -0.2919(3) 1.09560(10) 1.000 0.0709(5) . . . .
N1 N Uani 0.68190(10) 0.6411(4) 1.0216(2) 1.000 0.0870(10) . . . .
N2 N Uani 0.94986(9) -0.3124(3) 0.99580(10) 1.000 0.0551(6) . . . .
C1 C Uani 0.65070(10) 0.2691(3) 0.8102(2) 1.000 0.0469(6) . . . .
C2 C Uani 0.63920(10) 0.4278(4) 0.7250(2) 1.000 0.0626(6) . . . .
C3 C Uani 0.58260(10) 0.3982(4) 0.6275(2) 1.000 0.0737(12) . . . .
C4 C Uani 0.53580(10) 0.2125(4) 0.6145(2) 1.000 0.0698(6) . . . .
C5 C Uani 0.54630(10) 0.0545(4) 0.6988(2) 1.000 0.0675(8) . . . .
C6 C Uani 0.60330(10) 0.0817(4) 0.7957(2) 1.000 0.0566(6) . . . .
C7 C Uani 0.71340(10) 0.2992(3) 0.9147(2) 1.000 0.0450(6) . . . .
C8 C Uani 0.77540(10) 0.1606(3) 0.9405(2) 1.000 0.0414(6) . . . .
C9 C Uani 0.78020(10) -0.0149(3) 0.8614(2) 1.000 0.0441(6) . . . .
C10 C Uani 0.83710(10) -0.1637(3) 0.8813(2) 1.000 0.0446(6) . . . .
C11 C Uani 0.89840(10) -0.1558(3) 0.9828(2) 1.000 0.0457(6) . . . .
C12 C Uani 0.89690(10) 0.0239(3) 1.0597(2) 1.000 0.0484(6) . . . .
C13 C Uani 0.83950(10) 0.1718(3) 1.0401(2) 1.000 0.0445(6) . . . .
C14 C Uani 0.70070(10) 0.4871(4) 0.9803(2) 1.000 0.0574(6) . . . .
H1 H Uiso 1.03460 -0.39980 1.10290 1.000 0.1060 . . . .
H2 H Uiso 0.67010 0.55530 0.73370 1.000 0.0750 . . . .
H3 H Uiso 0.57610 0.50410 0.57030 1.000 0.0880 . . . .
H4 H Uiso 0.49710 0.19380 0.54910 1.000 0.0840 . . . .
H5 H Uiso 0.51480 -0.07130 0.69020 1.000 0.0810 . . . .
H6 H Uiso 0.61010 -0.02620 0.85200 1.000 0.0680 . . . .
H9 H Uiso 0.74240 -0.02460 0.79450 1.000 0.0530 . . . .
H12 H Uiso 0.93640 0.03830 1.12440 1.000 0.0580 . . . .
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 H1 109.00 . . . no
O1 N2 C11 112.74(16) . . . yes
C2 C1 C6 118.6(2) . . . no
C6 C1 C7 121.05(19) . . . no
C2 C1 C7 120.39(17) . . . no
C1 C2 C3 120.6(2) . . . no
C2 C3 C4 120.2(2) . . . no
C3 C4 C5 119.7(2) . . . no
C4 C5 C6 120.3(2) . . . no
C1 C6 C5 120.6(2) . . . no
C1 C7 C14 112.15(17) . . . no
C8 C7 C14 125.9(2) . . . no
C1 C7 C8 121.99(19) . . . no
C7 C8 C13 126.94(19) . . . no
C9 C8 C13 114.88(17) . . . no
C7 C8 C9 118.2(2) . . . no
C8 C9 C10 122.4(2) . . . no
Cl1 C10 C9 120.26(18) . . . yes
C9 C10 C11 121.7(2) . . . no
Cl1 C10 C11 118.03(14) . . . yes
N2 C11 C10 117.02(18) . . . yes
C10 C11 C12 116.90(17) . . . no
N2 C11 C12 126.1(2) . . . yes
C11 C12 C13 121.3(2) . . . no
Cl2 C13 C8 119.96(14) . . . yes
C8 C13 C12 122.68(19) . . . no
Cl2 C13 C12 117.36(18) . . . yes
N1 C14 C7 170.9(2) . . . yes
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
C8 C9 H9 119.00 . . . no
C10 C9 H9 119.00 . . . no
C11 C12 H12 119.00 . . . no
C13 C12 H12 119.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.728(2) . . yes
Cl2 C13 1.726(2) . . yes
O1 N2 1.3846(19) . . yes
N1 C14 1.146(3) . . yes
O1 H1 0.8200 . . no
N2 C11 1.304(3) . . yes
C1 C6 1.389(3) . . no
C1 C7 1.496(3) . . no
C1 C2 1.387(3) . . no
C2 C3 1.378(3) . . no
C3 C4 1.375(3) . . no
C4 C5 1.378(3) . . no
C5 C6 1.375(3) . . no
C7 C8 1.374(3) . . no
C7 C14 1.436(3) . . no
C8 C13 1.462(3) . . no
C8 C9 1.451(3) . . no
C9 C10 1.341(3) . . no
C10 C11 1.447(3) . . no
C11 C12 1.435(3) . . no
C12 C13 1.345(3) . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C9 H9 0.9300 . . no
C12 H12 0.9300 . . no
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 Cl1 0.8200 2.7300 3.4701(19) 152.00 3_747 yes
O1 H1 N2 0.8200 2.1600 2.817(2) 137.00 3_747 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
_geom_torsion_publ_flag
O1 N2 C11 C12 0.6(3) . . . . no
O1 N2 C11 C10 -179.46(16) . . . . no
C7 C1 C2 C3 178.48(19) . . . . no
C2 C1 C6 C5 0.1(3) . . . . no
C2 C1 C7 C8 -109.2(2) . . . . no
C2 C1 C7 C14 69.9(3) . . . . no
C7 C1 C6 C5 -179.3(2) . . . . no
C6 C1 C2 C3 -0.9(3) . . . . no
C6 C1 C7 C14 -110.7(2) . . . . no
C6 C1 C7 C8 70.2(3) . . . . no
C1 C2 C3 C4 1.3(3) . . . . no
C2 C3 C4 C5 -0.8(3) . . . . no
C3 C4 C5 C6 0.0(3) . . . . no
C4 C5 C6 C1 0.4(3) . . . . no
C1 C7 C8 C9 1.9(3) . . . . no
C14 C7 C8 C13 1.7(3) . . . . no
C14 C7 C8 C9 -177.1(2) . . . . no
C1 C7 C8 C13 -179.30(19) . . . . no
C13 C8 C9 C10 3.7(3) . . . . no
C7 C8 C9 C10 -177.3(2) . . . . no
C9 C8 C13 Cl2 176.69(15) . . . . no
C7 C8 C13 Cl2 -2.2(3) . . . . no
C7 C8 C13 C12 178.0(2) . . . . no
C9 C8 C13 C12 -3.1(3) . . . . no
C8 C9 C10 C11 -1.2(3) . . . . no
C8 C9 C10 Cl1 179.09(15) . . . . no
Cl1 C10 C11 N2 -2.3(3) . . . . no
C9 C10 C11 C12 -2.1(3) . . . . no
Cl1 C10 C11 C12 177.64(15) . . . . no
C9 C10 C11 N2 177.93(19) . . . . no
N2 C11 C12 C13 -177.4(2) . . . . no
C10 C11 C12 C13 2.7(3) . . . . no
C11 C12 C13 Cl2 -179.83(16) . . . . no
C11 C12 C13 C8 0.0(3) . . . . no
