#------------------------------------------------------------------------------ #$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 \a-(4-(hydroxyimino)-2,5-dichloro-2,5-cyclohexadien- 1-ylidene)-benzeneacetonitrile, C14H8Cl2N2O ; _journal_issue 2 _journal_name_full 'Zeitschrift f\"ur 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_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0677(3) 0.0564(3) 0.0636(3) -0.0071(2) 0.0215(3) 0.0178(2) Cl2 0.0729(4) 0.0627(4) 0.0561(3) -0.0105(2) 0.0140(3) 0.0135(3) O1 0.0572(9) 0.0810(10) 0.0677(9) 0.0084(9) 0.0072(7) 0.0301(8) N1 0.087(2) 0.0690(10) 0.101(2) -0.0180(10) 0.0210(10) 0.0290(10) N2 0.0495(9) 0.0590(10) 0.0580(10) 0.0130(8) 0.0177(8) 0.0193(8) C1 0.0435(9) 0.0380(10) 0.0600(10) 0.0054(9) 0.0164(8) 0.0100(8) C2 0.0580(10) 0.0470(10) 0.0750(10) 0.0150(10) 0.0070(10) 0.0015(9) C3 0.079(2) 0.061(2) 0.070(2) 0.0190(10) 0.0040(10) 0.0100(10) C4 0.0680(10) 0.0580(10) 0.0700(10) -0.0040(10) -0.0010(10) 0.0110(10) C5 0.0600(10) 0.0520(10) 0.086(2) -0.0030(10) 0.0140(10) -0.0030(10) C6 0.0560(10) 0.0430(10) 0.0710(10) 0.0080(10) 0.0190(10) 0.0031(9) C7 0.0461(9) 0.0370(10) 0.0550(10) 0.0064(8) 0.0195(8) 0.0062(8) C8 0.0456(9) 0.0370(10) 0.0460(10) 0.0091(8) 0.0203(8) 0.0056(7) C9 0.0453(9) 0.0450(10) 0.0440(10) 0.0070(8) 0.0160(8) 0.0083(8) C10 0.0500(10) 0.0410(10) 0.0480(10) 0.0060(8) 0.0224(8) 0.0079(8) C11 0.0459(9) 0.0460(10) 0.0500(10) 0.0112(8) 0.0216(8) 0.0120(8) C12 0.0460(10) 0.0550(10) 0.0460(10) 0.0105(9) 0.0162(8) 0.0092(9) C13 0.0500(10) 0.0440(10) 0.0440(10) 0.0074(8) 0.0209(8) 0.0064(8) C14 0.0530(10) 0.0490(10) 0.0690(10) 0.0010(10) 0.0160(10) 0.0130(10) 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