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#$Date: 2023-02-08 11:39:29 +0200 (Wed, 08 Feb 2023) $
#$Revision: 280814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106713.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_8106713
loop_
_publ_author_name
'You, Changming'
'Wang, Changqing'
_publ_section_title
;
 Crystal structure of
 2-benzoyl-3-(4-methoxyphenyl)cyclopropane-1,1-dicarbonitrile, C19H14N2O2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              897
_journal_page_last               898
_journal_paper_doi               10.1515/ncrs-2017-0052
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.32
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/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                 120.5880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.8907(8)
_cell_length_b                   12.0860(5)
_cell_length_c                   15.5260(7)
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.8
_cell_measurement_theta_min      2.18
_cell_volume                     3213.1(2)
_computing_data_collection       'Bruker SMART APEXII'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13416
_diffrn_reflns_theta_full        28.63
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.6700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                2291
_reflns_number_total             4055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0052_suppl.cif
_cod_data_source_block           exp_5
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8106713
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12536(16) 0.46622(17) 0.13246(17) 0.0817(6) Uani 1 1 d . . .
C2 C 0.0798(2) 0.5313(2) 0.1555(2) 0.1070(9) Uani 1 1 d . . .
C3 C 0.0119(3) 0.4929(3) 0.1426(3) 0.1237(13) Uani 1 1 d . . .
C4 C -0.0117(2) 0.3895(3) 0.1082(3) 0.1339(13) Uani 1 1 d . . .
C5 C 0.03325(14) 0.32125(19) 0.0857(2) 0.0872(7) Uani 1 1 d . . .
C6 C 0.10155(10) 0.35982(13) 0.09677(12) 0.0559(4) Uani 1 1 d . . .
C7 C 0.14958(10) 0.29359(13) 0.06900(14) 0.0603(4) Uani 1 1 d . . .
C8 C 0.13583(10) 0.17085(13) 0.05529(13) 0.0543(4) Uani 1 1 d . . .
C9 C 0.19223(9) 0.10020(13) 0.04533(12) 0.0516(4) Uani 1 1 d . . .
C10 C 0.11153(9) 0.12321(12) -0.04863(13) 0.0524(4) Uani 1 1 d . . .
C11 C 0.10767(11) 0.19373(15) -0.12574(15) 0.0672(5) Uani 1 1 d . . .
C12 C 0.05336(10) 0.03694(14) -0.08464(13) 0.0592(4) Uani 1 1 d . . .
C13 C 0.21478(9) -0.01325(13) 0.08595(12) 0.0503(4) Uani 1 1 d . . .
C14 C 0.17542(11) -0.07426(14) 0.12244(14) 0.0625(5) Uani 1 1 d . . .
C15 C 0.19799(12) -0.18060(16) 0.15694(16) 0.0700(5) Uani 1 1 d . . .
C16 C 0.26002(10) -0.22877(14) 0.15505(14) 0.0628(4) Uani 1 1 d . . .
C17 C 0.30008(11) -0.16970(16) 0.12021(15) 0.0685(5) Uani 1 1 d . . .
C18 C 0.27735(10) -0.06263(16) 0.08619(14) 0.0623(5) Uani 1 1 d . . .
C19 C 0.33745(14) -0.39023(19) 0.18261(18) 0.0970(7) Uani 1 1 d . . .
H19A H 0.3252 -0.3885 0.1143 0.146 Uiso 1 1 calc R . .
H19B H 0.3408 -0.4657 0.2038 0.146 Uiso 1 1 calc R . .
H19C H 0.3866 -0.3540 0.2242 0.146 Uiso 1 1 calc R . .
H1 H 0.1737(16) 0.485(2) 0.140(2) 0.123(10) Uiso 1 1 d . . .
H2 H 0.0933(18) 0.610(3) 0.178(3) 0.168(12) Uiso 1 1 d . . .
H3 H -0.0172(19) 0.540(2) 0.160(2) 0.154(11) Uiso 1 1 d . . .
H4 H -0.061(2) 0.355(3) 0.088(3) 0.174(13) Uiso 1 1 d . . .
H5 H 0.0155(12) 0.2539(17) 0.0579(16) 0.081(6) Uiso 1 1 d . . .
H6 H 0.1090(9) 0.1384(12) 0.0842(11) 0.051(4) Uiso 1 1 d . . .
H7 H 0.2308(9) 0.1426(13) 0.0423(12) 0.057(4) Uiso 1 1 d . . .
H8 H 0.1320(11) -0.0418(14) 0.1267(14) 0.071(5) Uiso 1 1 d . . .
H9 H 0.1698(12) -0.2197(17) 0.1826(16) 0.090(6) Uiso 1 1 d . . .
H10 H 0.3045(11) -0.0213(15) 0.0617(15) 0.077(6) Uiso 1 1 d . . .
H11 H 0.3446(13) -0.2021(16) 0.1176(16) 0.094(7) Uiso 1 1 d . . .
N1 N 0.10417(13) 0.24665(18) -0.18834(18) 0.1087(7) Uani 1 1 d . . .
N2 N 0.00791(10) -0.03160(14) -0.11037(14) 0.0850(5) Uani 1 1 d . . .
O1 O 0.19882(9) 0.33535(10) 0.05534(14) 0.0966(5) Uani 1 1 d . . .
O2 O 0.27790(9) -0.33477(11) 0.19075(12) 0.0872(4) Uani 1 1 d . . .
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'
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
C2 C1 C6 119.9(3) . .
C3 C2 C1 120.5(3) . .
C2 C3 C4 120.1(3) . .
C3 C4 C5 120.8(3) . .
C6 C5 C4 119.7(3) . .
C5 C6 C1 118.95(19) . .
C5 C6 C7 122.19(17) . .
C1 C6 C7 118.83(17) . .
O1 C7 C6 121.89(15) . .
O1 C7 C8 119.40(15) . .
C6 C7 C8 118.70(14) . .
C9 C8 C7 119.42(14) . .
C9 C8 C10 61.66(11) . .
C7 C8 C10 117.02(14) . .
C8 C9 C13 124.87(14) . .
C8 C9 C10 61.13(11) . .
C13 C9 C10 120.78(13) . .
C11 C10 C12 114.39(15) . .
C11 C10 C8 120.34(14) . .
C12 C10 C8 115.98(13) . .
C11 C10 C9 118.74(13) . .
C12 C10 C9 118.54(13) . .
C8 C10 C9 57.20(10) . .
N1 C11 C10 177.9(2) . .
N2 C12 C10 178.1(2) . .
C18 C13 C14 117.69(16) . .
C18 C13 C9 118.66(14) . .
C14 C13 C9 123.65(14) . .
C15 C14 C13 120.96(17) . .
C14 C15 C16 120.29(18) . .
C17 C16 O2 124.35(17) . .
C17 C16 C15 119.69(17) . .
O2 C16 C15 115.96(17) . .
C16 C17 C18 119.70(17) . .
C13 C18 C17 121.67(17) . .
C16 O2 C19 117.50(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.377(4) .
C1 C6 1.385(3) .
C2 C3 1.343(4) .
C3 C4 1.346(5) .
C4 C5 1.385(3) .
C5 C6 1.362(3) .
C6 C7 1.469(2) .
C7 O1 1.2125(18) .
C7 C8 1.504(2) .
C8 C9 1.479(2) .
C8 C10 1.541(2) .
C9 C13 1.480(2) .
C9 C10 1.549(2) .
C10 C11 1.439(2) .
C10 C12 1.442(2) .
C11 N1 1.136(2) .
C12 N2 1.138(2) .
C13 C18 1.379(2) .
C13 C14 1.389(2) .
C14 C15 1.377(2) .
C15 C16 1.378(2) .
C16 C17 1.370(3) .
C16 O2 1.369(2) .
C17 C18 1.384(3) .
C19 O2 1.422(2) .
