#------------------------------------------------------------------------------
#$Date: 2023-12-11 12:34:32 +0200 (Mon, 11 Dec 2023) $
#$Revision: 288214 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/77/8107718.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_8107718
loop_
_publ_author_name
'Yanping, Yi'
_publ_section_title
;
 Crystal structure of 2-benzoyl-3-(3,4-dichlorophenyl)cyclopropane-1,1-
 dicarbonitrile, C18H10Cl2N2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              65
_journal_page_last               66
_journal_paper_doi               10.1515/ncrs-2014-9063
_journal_volume                  230
_journal_year                    2015
_chemical_formula_sum            'C18 H10 Cl2 N2 O'
_chemical_formula_weight         341.19
_chemical_name_common
;
2-benzoyl-3-(3,4-dichlorophenyl)cyclopropane-1,1-
dicarbonitrile
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                98.491(2)
_cell_angle_beta                 100.571(2)
_cell_angle_gamma                107.434(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8195(5)
_cell_length_b                   9.6727(8)
_cell_length_c                   13.268(1)
_cell_volume                     801.44(11)
_diffrn_ambient_temperature      296
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.412
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             350
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2680
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_gt          0.1224
_cod_data_source_file            Z-2015-065.cif
_cod_data_source_block           1
_cod_database_code               8107718
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-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 0.35358(9) 1.06310(7) 0.71230(5) 1.000 0.0685(2) . . . .
Cl2 Cl Uani 0.72946(9) 0.93401(7) 0.74742(5) 1.000 0.0760(2) . . . .
O1 O Uani -0.1875(2) 0.7192(2) 0.14190(10) 1.000 0.0687(5) . . . .
N1 N Uani -0.4876(3) 0.4999(2) 0.2530(2) 1.000 0.0694(6) . . . .
N2 N Uani 0.0399(3) 0.3704(2) 0.3884(2) 1.000 0.0715(8) . . . .
C1 C Uani 0.3072(4) 0.7725(4) -0.0936(2) 1.000 0.0841(14) . . . .
C2 C Uani 0.3717(4) 0.6991(3) -0.0212(2) 1.000 0.0721(8) . . . .
C3 C Uani 0.2665(3) 0.6699(3) 0.0567(2) 1.000 0.0568(8) . . . .
C4 C Uani 0.0921(3) 0.7137(2) 0.06160(10) 1.000 0.0481(6) . . . .
C5 C Uani 0.0271(4) 0.7865(3) -0.0138(2) 1.000 0.0816(12) . . . .
C6 C Uani 0.1349(5) 0.8163(4) -0.0899(2) 1.000 0.1044(14) . . . .
C7 C Uani -0.0239(3) 0.6918(2) 0.1447(2) 1.000 0.0498(6) . . . .
C8 C Uani 0.0694(3) 0.6449(2) 0.2405(2) 1.000 0.0464(6) . . . .
C9 C Uani 0.0611(3) 0.7263(2) 0.3436(2) 1.000 0.0460(6) . . . .
C10 C Uani -0.0804(3) 0.5628(2) 0.3019(2) 1.000 0.0461(6) . . . .
C11 C Uani 0.2324(3) 0.7755(2) 0.4417(2) 1.000 0.0435(6) . . . .
C12 C Uani 0.2247(3) 0.8823(2) 0.5211(2) 1.000 0.0456(6) . . . .
C13 C Uani 0.3744(3) 0.9313(2) 0.6155(2) 1.000 0.0475(6) . . . .
C14 C Uani 0.5364(3) 0.8726(2) 0.6307(2) 1.000 0.0508(6) . . . .
C15 C Uani 0.5470(3) 0.7666(2) 0.5529(2) 1.000 0.0546(6) . . . .
C16 C Uani 0.3973(3) 0.7176(2) 0.4582(2) 1.000 0.0503(6) . . . .
C17 C Uani -0.3087(3) 0.5292(2) 0.2709(2) 1.000 0.0525(6) . . . .
C(18) C Uani -0.0181(3) 0.4523(2) 0.3495(2) 1.000 0.0521(6) . . . .
H1 H Uiso 0.380(4) 0.790(3) -0.147(2) 1.000 0.090(8) . . . .
H2 H Uiso 0.486(4) 0.662(3) -0.026(2) 1.000 0.092(8) . . . .
H3 H Uiso 0.304(3) 0.610(2) 0.105(2) 1.000 0.073(7) . . . .
H4 H Uiso -0.089(4) 0.824(3) -0.004(2) 1.000 0.087(8) . . . .
H5 H Uiso 0.078(5) 0.851(4) -0.150(3) 1.000 0.140(10) . . . .
H6 H Uiso 0.188(3) 0.609(2) 0.235(2) 1.000 0.044(5) . . . .
H7 H Uiso -0.025(3) 0.790(2) 0.3360(10) 1.000 0.042(5) . . . .
H8 H Uiso 0.111(3) 0.924(2) 0.511(2) 1.000 0.050(5) . . . .
H9 H Uiso 0.653(3) 0.728(2) 0.565(2) 1.000 0.068(6) . . . .
H10 H Uiso 0.403(3) 0.645(2) 0.407(2) 1.000 0.054(6) . . . .
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 C(18) C10 176.8(2) . . . yes
C2 C1 C6 119.9(3) . . . no
C1 C2 C3 120.6(3) . . . no
C2 C3 C4 120.3(2) . . . no
C3 C4 C5 118.3(2) . . . no
C3 C4 C7 123.59(18) . . . no
C5 C4 C7 118.1(2) . . . no
C4 C5 C6 120.7(3) . . . no
C1 C6 C5 120.3(3) . . . no
O1 C7 C4 122.1(2) . . . yes
O1 C7 C8 118.2(2) . . . yes
C4 C7 C8 119.55(18) . . . no
C7 C8 C9 115.94(18) . . . no
C7 C8 C10 118.58(19) . . . no
C9 C8 C10 61.14(15) . . . no
C8 C9 C10 60.67(15) . . . no
C8 C9 C11 125.64(19) . . . no
C10 C9 C11 122.12(18) . . . no
C(18) C10 C8 115.67(18) . . . yes
C(18) C10 C9 117.8(2) . . . yes
C(18) C10 C17 113.88(18) . . . yes
C8 C10 C9 58.20(14) . . . no
C8 C10 C17 122.2(2) . . . no
C9 C10 C17 118.18(18) . . . no
C9 C11 C12 117.89(19) . . . no
C9 C11 C16 123.5(2) . . . no
C12 C11 C16 118.7(2) . . . no
C11 C12 C13 121.5(2) . . . no
Cl1 C13 C12 119.26(17) . . . yes
Cl1 C13 C14 121.63(19) . . . yes
C12 C13 C14 119.1(2) . . . no
Cl2 C14 C13 120.27(18) . . . yes
Cl2 C14 C15 119.45(17) . . . yes
C13 C14 C15 120.3(2) . . . no
C14 C15 C16 120.7(2) . . . no
C11 C16 C15 119.8(2) . . . no
N1 C17 C10 175.3(3) . . . yes
C2 C1 H1 119.2(17) . . . no
C6 C1 H1 120.9(17) . . . no
C1 C2 H2 120.5(16) . . . no
C3 C2 H2 118.9(16) . . . no
C2 C3 H3 120.9(13) . . . no
C4 C3 H3 118.5(13) . . . no
C4 C5 H4 115.9(15) . . . no
C6 C5 H4 123.1(16) . . . no
C1 C6 H5 117(2) . . . no
C5 C6 H5 122(2) . . . no
C7 C8 H6 115.5(15) . . . no
C9 C8 H6 120.4(15) . . . no
C10 C8 H6 114.6(13) . . . no
C8 C9 H7 112.8(8) . . . no
C10 C9 H7 109.6(11) . . . no
C11 C9 H7 114.7(9) . . . no
C11 C12 H8 119.8(15) . . . no
C13 C12 H8 118.7(15) . . . no
C14 C15 H9 118.9(16) . . . no
C16 C15 H9 120.4(16) . . . no
C11 C16 H10 119.8(15) . . . no
C15 C16 H10 120.4(15) . . . 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 C13 1.728(2) . . yes
Cl2 C14 1.731(3) . . yes
O1 C7 1.217(3) . . yes
N1 C17 1.137(3) . . yes
C(18) N2 1.133(3) . . yes
C(18) C10 1.447(3) . . yes
C1 C2 1.362(4) . . no
C1 C6 1.370(5) . . no
C2 C3 1.378(4) . . no
C3 C4 1.386(3) . . no
C4 C5 1.388(3) . . no
C4 C7 1.475(3) . . no
C5 C6 1.369(4) . . no
C7 C8 1.508(3) . . no
C8 C9 1.494(3) . . no
C8 C10 1.532(3) . . no
C9 C10 1.539(3) . . no
C9 C11 1.487(3) . . no
C10 C17 1.456(3) . . no
C11 C12 1.383(3) . . no
C11 C16 1.396(3) . . no
C12 C13 1.379(3) . . no
C13 C14 1.383(3) . . no
C14 C15 1.372(3) . . no
C15 C16 1.382(3) . . no
C1 H1 0.94(3) . . no
C2 H2 0.96(3) . . no
C3 H3 0.98(2) . . no
C5 H4 0.99(3) . . no
C6 H5 0.97(4) . . no
C8 H6 0.98(2) . . no
C9 H7 0.97(2) . . no
C12 H8 0.97(2) . . no
C15 H9 0.91(2) . . no
C16 H10 0.92(2) . . 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
C5 H4 O1 0.99(3) 2.42(3) 2.787(3) 101.1(18) . yes
C9 H7 O1 0.97(2) 2.511(13) 2.873(3) 101.8(10) . yes
C15 H9 N2 0.91(2) 2.56(2) 3.469(3) 176.2(19) 2_666 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
C6 C1 C2 C3 -0.8(5) . . . . no
C2 C1 C6 C5 -0.1(5) . . . . no
C1 C2 C3 C4 0.7(4) . . . . no
C2 C3 C4 C5 0.3(4) . . . . no
C2 C3 C4 C7 -177.6(2) . . . . no
C3 C4 C5 C6 -1.1(4) . . . . no
C7 C4 C5 C6 176.9(2) . . . . no
C3 C4 C7 O1 -173.3(2) . . . . no
C3 C4 C7 C8 11.4(3) . . . . no
C5 C4 C7 O1 8.9(3) . . . . no
C5 C4 C7 C8 -166.5(2) . . . . no
C4 C5 C6 C1 1.0(5) . . . . no
O1 C7 C8 C9 -40.5(3) . . . . no
O1 C7 C8 C10 29.2(3) . . . . no
C4 C7 C8 C9 135.0(2) . . . . no
C4 C7 C8 C10 -155.26(19) . . . . no
C7 C8 C9 C10 109.8(2) . . . . no
C7 C8 C9 C11 -139.8(2) . . . . no
C10 C8 C9 C11 110.3(2) . . . . no
C7 C8 C10 C(18) 146.3(2) . . . . no
C7 C8 C10 C9 -105.6(2) . . . . no
C7 C8 C10 C17 -0.2(3) . . . . no
C9 C8 C10 C(18) -108.1(2) . . . . no
C9 C8 C10 C17 105.4(2) . . . . no
C8 C9 C10 C(18) 104.4(2) . . . . no
C8 C9 C10 C17 -112.3(2) . . . . no
C11 C9 C10 C(18) -11.4(3) . . . . no
C11 C9 C10 C8 -115.9(2) . . . . no
C11 C9 C10 C17 131.8(2) . . . . no
C8 C9 C11 C12 162.9(2) . . . . no
C8 C9 C11 C16 -18.4(3) . . . . no
C10 C9 C11 C12 -122.3(2) . . . . no
C10 C9 C11 C16 56.5(3) . . . . no
C9 C11 C12 C13 178.37(19) . . . . no
C16 C11 C12 C13 -0.5(3) . . . . no
C9 C11 C16 C15 -178.2(2) . . . . no
C12 C11 C16 C15 0.6(3) . . . . no
C11 C12 C13 Cl1 -179.05(17) . . . . no
C11 C12 C13 C14 0.3(3) . . . . no
Cl1 C13 C14 Cl2 -1.8(3) . . . . no
Cl1 C13 C14 C15 179.08(17) . . . . no
C12 C13 C14 Cl2 178.88(16) . . . . no
C12 C13 C14 C15 -0.3(3) . . . . no
Cl2 C14 C15 C16 -178.77(16) . . . . no
C13 C14 C15 C16 0.4(3) . . . . no
C14 C15 C16 C11 -0.6(3) . . . . no
