#------------------------------------------------------------------------------
#$Date: 2023-05-09 12:16:48 +0300 (Tue, 09 May 2023) $
#$Revision: 283628 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107155.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_8107155
loop_
_publ_author_name
'Wang, Kai'
'Chen, Qiang'
'Xiao, Jian'
_publ_section_title
;
 Crystal structure of 2,4-dibenzoyl-N,N-dimethylbenzenamine, C22H19NO2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1235
_journal_page_last               1236
_journal_paper_doi               10.1515/ncrs-2016-0151
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 123.946(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7728(19)
_cell_length_b                   7.9765(12)
_cell_length_c                   20.451(3)
_cell_measurement_reflns_used    10046
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.9
_cell_volume                     1728.5(5)
_computing_cell_refinement       'CAD-4 Software '
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL '
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXTL '
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.1726
_diffrn_reflns_av_sigmaI/netI    0.1070
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10046
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.052(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0492
_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)+(0.0581P)²+0.0272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                2697
_reflns_number_total             3383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0151_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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_cell_volume        1728.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107155
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_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_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
O1 O 0.33289(11) 0.8899(2) 0.07217(7) 0.0781(4) Uani 1 1 d . . .
O2 O 0.24768(10) 0.76442(13) 0.36947(7) 0.0579(3) Uani 1 1 d . . .
N1 N 0.52798(11) 0.83648(16) 0.43202(7) 0.0519(4) Uani 1 1 d . . .
C14 C 0.27577(11) 0.67266(16) 0.33420(7) 0.0382(3) Uani 1 1 d . . .
C11 C 0.46157(11) 0.84040(17) 0.35182(8) 0.0414(3) Uani 1 1 d . . .
C12 C 0.34993(11) 0.74243(16) 0.30369(7) 0.0381(3) Uani 1 1 d . . .
C9 C 0.43824(12) 0.94241(19) 0.23249(9) 0.0474(4) Uani 1 1 d . . .
H9 H 0.4671 1.0113 0.2091 0.057 Uiso 1 1 calc R . .
C15 C 0.23266(10) 0.49418(16) 0.31823(7) 0.0363(3) Uani 1 1 d . . .
C8 C 0.33100(12) 0.84220(17) 0.18439(8) 0.0423(3) Uani 1 1 d . . .
C7 C 0.27137(13) 0.8450(2) 0.09814(9) 0.0501(4) Uani 1 1 d . . .
C13 C 0.29031(11) 0.74308(16) 0.22229(8) 0.0397(3) Uani 1 1 d . . .
H13 H 0.2203 0.6745 0.1918 0.048 Uiso 1 1 calc R . .
C10 C 0.50114(11) 0.94120(19) 0.31270(9) 0.0477(4) Uani 1 1 d . . .
H10 H 0.5721 1.0087 0.3424 0.057 Uiso 1 1 calc R . .
C20 C 0.13796(12) 0.44626(19) 0.32860(9) 0.0480(4) Uani 1 1 d . . .
H20 H 0.0999 0.5257 0.3421 0.058 Uiso 1 1 calc R . .
C1 C 0.13673(13) 0.7931(2) 0.04205(8) 0.0489(4) Uani 1 1 d . . .
C17 C 0.25130(13) 0.2083(2) 0.28954(9) 0.0545(4) Uani 1 1 d . . .
H17 H 0.2895 0.1280 0.2765 0.065 Uiso 1 1 calc R . .
C16 C 0.28844(12) 0.37398(18) 0.29823(8) 0.0449(4) Uani 1 1 d . . .
H16 H 0.3511 0.4049 0.2906 0.054 Uiso 1 1 calc R . .
C18 C 0.15772(14) 0.16143(19) 0.30015(9) 0.0565(4) Uani 1 1 d . . .
H18 H 0.1334 0.0497 0.2947 0.068 Uiso 1 1 calc R . .
C19 C 0.10063(14) 0.2803(2) 0.31871(10) 0.0583(4) Uani 1 1 d . . .
H19 H 0.0363 0.2489 0.3247 0.070 Uiso 1 1 calc R . .
C2 C 0.04414(13) 0.8227(2) 0.05660(9) 0.0525(4) Uani 1 1 d . . .
H2 H 0.0661 0.8700 0.1042 0.063 Uiso 1 1 calc R . .
C3 C -0.08077(15) 0.7820(2) 0.00031(11) 0.0681(5) Uani 1 1 d . . .
H3 H -0.1428 0.8035 0.0097 0.082 Uiso 1 1 calc R . .
C6 C 0.10247(16) 0.7236(2) -0.02963(10) 0.0623(5) Uani 1 1 d . . .
H6 H 0.1633 0.7065 -0.0405 0.075 Uiso 1 1 calc R . .
C4 C -0.11231(17) 0.7095(3) -0.06947(11) 0.0790(6) Uani 1 1 d . . .
H4 H -0.1957 0.6800 -0.1068 0.095 Uiso 1 1 calc R . .
C22 C 0.62596(14) 0.9609(2) 0.47885(10) 0.0657(5) Uani 1 1 d . . .
H22A H 0.7030 0.9269 0.4849 0.099 Uiso 1 1 calc R . .
H22B H 0.6394 0.9703 0.5298 0.099 Uiso 1 1 calc R . .
H22C H 0.5999 1.0675 0.4527 0.099 Uiso 1 1 calc R . .
C5 C -0.02127(19) 0.6801(3) -0.08460(10) 0.0746(6) Uani 1 1 d . . .
H5 H -0.0435 0.6309 -0.1319 0.090 Uiso 1 1 calc R . .
C21 C 0.52899(14) 0.6914(2) 0.47520(9) 0.0587(4) Uani 1 1 d . . .
H21A H 0.4728 0.7104 0.4917 0.088 Uiso 1 1 calc R . .
H21B H 0.6130 0.6735 0.5207 0.088 Uiso 1 1 calc R . .
H21C H 0.5018 0.5943 0.4418 0.088 Uiso 1 1 calc R . .
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
C11 N1 C21 122.59(11) . .
C11 N1 C22 120.24(13) . .
C21 N1 C22 115.47(12) . .
O2 C14 C15 120.59(12) . .
O2 C14 C12 119.18(11) . .
C15 C14 C12 120.18(12) . .
N1 C11 C10 121.05(12) . .
N1 C11 C12 121.81(12) . .
C10 C11 C12 117.13(13) . .
C13 C12 C11 119.39(12) . .
C13 C12 C14 116.59(10) . .
C11 C12 C14 122.29(12) . .
C10 C9 C8 121.75(13) . .
C10 C9 H9 119.1 . .
C8 C9 H9 119.1 . .
C16 C15 C20 119.24(13) . .
C16 C15 C14 122.41(12) . .
C20 C15 C14 118.24(13) . .
C13 C8 C9 116.94(13) . .
C13 C8 C7 124.55(12) . .
C9 C8 C7 118.49(12) . .
O1 C7 C8 119.62(13) . .
O1 C7 C1 119.35(14) . .
C8 C7 C1 121.02(12) . .
C12 C13 C8 122.83(12) . .
C12 C13 H13 118.6 . .
C8 C13 H13 118.6 . .
C9 C10 C11 121.87(12) . .
C9 C10 H10 119.1 . .
C11 C10 H10 119.1 . .
C19 C20 C15 119.87(15) . .
C19 C20 H20 120.1 . .
C15 C20 H20 120.1 . .
C6 C1 C2 119.26(14) . .
C6 C1 C7 117.95(14) . .
C2 C1 C7 122.62(14) . .
C18 C17 C16 120.26(15) . .
C18 C17 H17 119.9 . .
C16 C17 H17 119.9 . .
C17 C16 C15 120.25(14) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C19 C18 C17 119.80(14) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
C18 C19 C20 120.57(14) . .
C18 C19 H19 119.7 . .
C20 C19 H19 119.7 . .
C3 C2 C1 120.24(17) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C4 C3 C2 119.62(18) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C5 C6 C1 120.21(18) . .
C5 C6 H6 119.9 . .
C1 C6 H6 119.9 . .
C3 C4 C5 120.58(16) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
N1 C22 H22A 109.5 . .
N1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
N1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C6 C5 C4 120.04(18) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
N1 C21 H21A 109.5 . .
N1 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
N1 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.2224(18) .
O2 C14 1.2140(17) .
N1 C11 1.3626(19) .
N1 C21 1.452(2) .
N1 C22 1.4595(18) .
C14 C15 1.4953(18) .
C14 C12 1.5021(19) .
C11 C10 1.412(2) .
C11 C12 1.4301(17) .
C12 C13 1.3912(19) .
C9 C10 1.365(2) .
C9 C8 1.4064(19) .
C9 H9 0.9300 .
C15 C16 1.385(2) .
C15 C20 1.3931(19) .
C8 C13 1.3950(19) .
C8 C7 1.480(2) .
C7 C1 1.497(2) .
C13 H13 0.9300 .
C10 H10 0.9300 .
C20 C19 1.383(2) .
C20 H20 0.9300 .
C1 C6 1.390(2) .
C1 C2 1.391(2) .
C17 C18 1.380(2) .
C17 C16 1.382(2) .
C17 H17 0.9300 .
C16 H16 0.9300 .
C18 C19 1.372(2) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C2 C3 1.388(2) .
C2 H2 0.9300 .
C3 C4 1.375(3) .
C3 H3 0.9300 .
C6 C5 1.378(3) .
C6 H6 0.9300 .
C4 C5 1.380(3) .
C4 H4 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C5 H5 0.9300 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
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
C21 H21A O2 0.9600 2.5800 3.041(2) 109.00 . 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
C21 N1 C11 C10 -151.88(14) . . . .
C22 N1 C11 C10 12.6(2) . . . .
C21 N1 C11 C12 27.64(19) . . . .
C22 N1 C11 C12 -167.89(13) . . . .
N1 C11 C12 C13 -175.97(12) . . . .
C10 C11 C12 C13 3.57(18) . . . .
N1 C11 C12 C14 19.54(18) . . . .
C10 C11 C12 C14 -160.92(12) . . . .
O2 C14 C12 C13 -116.19(14) . . . .
C15 C14 C12 C13 61.27(15) . . . .
O2 C14 C12 C11 48.71(18) . . . .
C15 C14 C12 C11 -133.83(12) . . . .
O2 C14 C15 C16 -162.00(13) . . . .
C12 C14 C15 C16 20.57(17) . . . .
O2 C14 C15 C20 14.09(18) . . . .
C12 C14 C15 C20 -163.34(11) . . . .
C10 C9 C8 C13 1.0(2) . . . .
C10 C9 C8 C7 -177.36(13) . . . .
C13 C8 C7 O1 -156.50(16) . . . .
C9 C8 C7 O1 21.7(2) . . . .
C13 C8 C7 C1 23.3(2) . . . .
C9 C8 C7 C1 -158.45(13) . . . .
C11 C12 C13 C8 -3.23(19) . . . .
C14 C12 C13 C8 162.13(12) . . . .
C9 C8 C13 C12 0.91(19) . . . .
C7 C8 C13 C12 179.15(12) . . . .
C8 C9 C10 C11 -0.5(2) . . . .
N1 C11 C10 C9 177.74(13) . . . .
C12 C11 C10 C9 -1.8(2) . . . .
C16 C15 C20 C19 -0.1(2) . . . .
C14 C15 C20 C19 -176.36(12) . . . .
O1 C7 C1 C6 29.3(2) . . . .
C8 C7 C1 C6 -150.50(15) . . . .
O1 C7 C1 C2 -145.97(17) . . . .
C8 C7 C1 C2 34.2(2) . . . .
C18 C17 C16 C15 0.5(2) . . . .
C20 C15 C16 C17 -0.7(2) . . . .
C14 C15 C16 C17 175.37(12) . . . .
C16 C17 C18 C19 0.6(2) . . . .
C17 C18 C19 C20 -1.4(2) . . . .
C15 C20 C19 C18 1.2(2) . . . .
C6 C1 C2 C3 0.5(2) . . . .
C7 C1 C2 C3 175.76(14) . . . .
C1 C2 C3 C4 1.1(3) . . . .
C2 C1 C6 C5 -1.9(3) . . . .
C7 C1 C6 C5 -177.38(15) . . . .
C2 C3 C4 C5 -1.3(3) . . . .
C1 C6 C5 C4 1.7(3) . . . .
C3 C4 C5 C6 -0.1(3) . . . .
