#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/92/2209228.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209228
loop_
_publ_author_name
'Xue-Mei Li'
'Li-Ping Du'
'Shu-Sheng Zhang'
_publ_section_title
3,3'-Dimethyl-2,2'-dinitro-N,N'-(o-phenylene)dibenzamide
_journal_coeditor_code           IS2039
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2535
_journal_page_last               o2536
_journal_paper_doi               10.1107/S1600536806019076
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H18 N4 O6'
_chemical_formula_moiety         'C22 H18 N4 O6'
_chemical_formula_sum            'C22 H18 N4 O6'
_chemical_formula_weight         434.40
_chemical_name_systematic
;
3,3'-Dimethyl-2,2'-dinitro-N,N'-(o-phenylene)dibenzamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.301(3)
_cell_angle_beta                 65.394(3)
_cell_angle_gamma                77.029(3)
_cell_formula_units_Z            2
_cell_length_a                   9.607(2)
_cell_length_b                   10.542(2)
_cell_length_c                   11.408(3)
_cell_measurement_reflns_used    1954
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      2.4
_cell_volume                     1023.1(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5827
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0625
_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)+(0.0944P)²+0.5433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1864
_reflns_number_gt                3019
_reflns_number_total             3943
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2039.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2209228
_cod_database_fobs_code          2209228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.5133(4) 0.8983(3) 0.1763(3) 0.1205(12) Uani d . 1
O O2 0.6174(3) 0.8783(2) 0.3108(2) 0.0807(7) Uani d . 1
O O3 0.43719(18) 0.67844(17) 0.46133(15) 0.0466(4) Uani d . 1
O O4 0.97132(19) 0.45546(16) 0.66248(18) 0.0515(5) Uani d . 1
O O5 1.0133(4) 0.1646(3) 0.8634(3) 0.1157(11) Uani d . 1
O O6 0.8042(3) 0.2330(3) 0.8391(2) 0.1129(11) Uani d . 1
N N1 0.5980(3) 0.8362(2) 0.2243(3) 0.0645(7) Uani d . 1
N N2 0.6725(2) 0.61657(18) 0.47493(17) 0.0389(4) Uani d . 1
H H2A 0.7715 0.5876 0.4315 0.047 Uiso calc R 1
N N3 0.7699(2) 0.42272(18) 0.62302(18) 0.0394(4) Uani d . 1
H H3A 0.7407 0.3733 0.5846 0.047 Uiso calc R 1
N N4 0.9386(3) 0.1840(2) 0.7968(2) 0.0603(6) Uani d . 1
C C1 0.6745(3) 0.7010(3) 0.1772(2) 0.0476(6) Uani d . 1
C C2 0.7546(3) 0.6719(3) 0.0450(3) 0.0622(8) Uani d . 1
C C3 0.8175(3) 0.5420(4) 0.0087(3) 0.0678(9) Uani d . 1
H H3B 0.8696 0.5188 -0.0787 0.081 Uiso calc R 1
C C4 0.8056(3) 0.4456(3) 0.0976(3) 0.0620(8) Uani d . 1
H H4A 0.8465 0.3588 0.0696 0.074 Uiso calc R 1
C C5 0.7336(3) 0.4770(3) 0.2273(3) 0.0500(6) Uani d . 1
H H5A 0.7297 0.4119 0.2870 0.060 Uiso calc R 1
C C6 0.6666(3) 0.6060(2) 0.2692(2) 0.0405(5) Uani d . 1
C C7 0.5801(2) 0.6390(2) 0.4110(2) 0.0371(5) Uani d . 1
C C8 0.6167(2) 0.6378(2) 0.6101(2) 0.0372(5) Uani d . 1
C C9 0.5163(3) 0.7549(2) 0.6702(2) 0.0456(6) Uani d . 1
H H9A 0.4851 0.8202 0.6218 0.055 Uiso calc R 1
C C10 0.4632(3) 0.7735(3) 0.8016(3) 0.0527(6) Uani d . 1
H H10A 0.3964 0.8516 0.8415 0.063 Uiso calc R 1
C C11 0.5085(3) 0.6772(3) 0.8745(2) 0.0548(7) Uani d . 1
H H11A 0.4709 0.6898 0.9632 0.066 Uiso calc R 1
C C12 0.6099(3) 0.5621(3) 0.8151(2) 0.0474(6) Uani d . 1
H H12A 0.6412 0.4976 0.8641 0.057 Uiso calc R 1
C C13 0.6653(2) 0.5422(2) 0.6832(2) 0.0377(5) Uani d . 1
C C14 0.9122(2) 0.3849(2) 0.6244(2) 0.0369(5) Uani d . 1
C C15 1.0013(2) 0.2490(2) 0.5739(2) 0.0375(5) Uani d . 1
C C16 1.0226(3) 0.1517(2) 0.6577(2) 0.0420(5) Uani d . 1
C C17 1.1165(3) 0.0283(2) 0.6159(2) 0.0451(6) Uani d . 1
C C18 1.1930(3) 0.0054(2) 0.4835(3) 0.0491(6) Uani d . 1
H H18A 1.2582 -0.0756 0.4514 0.059 Uiso calc R 1
C C19 1.1748(3) 0.0994(2) 0.3983(3) 0.0514(6) Uani d . 1
H H19A 1.2276 0.0810 0.3100 0.062 Uiso calc R 1
C C20 1.0787(3) 0.2210(2) 0.4428(2) 0.0465(6) Uani d . 1
H H20A 1.0662 0.2836 0.3846 0.056 Uiso calc R 1
C C21 0.7804(5) 0.7769(5) -0.0545(3) 0.0991(14) Uani d . 1
H H21A 0.8387 0.7371 -0.1393 0.149 Uiso calc R 1
H H21B 0.8381 0.8327 -0.0392 0.149 Uiso calc R 1
H H21C 0.6808 0.8275 -0.0479 0.149 Uiso calc R 1
C C22 1.1334(4) -0.0781(3) 0.7071(3) 0.0649(8) Uani d . 1
H H22A 1.0734 -0.0454 0.7944 0.097 Uiso calc R 1
H H22B 1.2419 -0.1064 0.6918 0.097 Uiso calc R 1
H H22C 1.0957 -0.1501 0.6930 0.097 Uiso calc R 1
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_publ_flag
O2 N1 O1 123.4(3) ?
O2 N1 C1 119.0(2) ?
O1 N1 C1 117.5(3) ?
C7 N2 C8 123.9(2) yes
C7 N2 H2A 118.1 ?
C8 N2 H2A 118.1 ?
C14 N3 C13 122.2(2) yes
C14 N3 H3A 118.9 ?
C13 N3 H3A 118.9 ?
O6 N4 O5 122.2(3) ?
O6 N4 C16 119.1(2) ?
O5 N4 C16 118.6(2) ?
C6 C1 C2 122.4(3) ?
C6 C1 N1 117.4(2) ?
C2 C1 N1 120.2(2) ?
C3 C2 C1 116.5(3) ?
C3 C2 C21 121.0(3) ?
C1 C2 C21 122.3(3) ?
C4 C3 C2 122.2(3) ?
C4 C3 H3B 118.9 ?
C2 C3 H3B 118.9 ?
C5 C4 C3 120.3(3) ?
C5 C4 H4A 119.8 ?
C3 C4 H4A 119.8 ?
C4 C5 C6 119.9(3) ?
C4 C5 H5A 120.1 ?
C6 C5 H5A 120.1 ?
C5 C6 C1 118.5(2) ?
C5 C6 C7 119.7(2) ?
C1 C6 C7 121.7(2) ?
O3 C7 N2 124.7(2) ?
O3 C7 C6 121.5(2) ?
N2 C7 C6 113.7(2) yes
C13 C8 C9 119.5(2) ?
C13 C8 N2 119.72(19) ?
C9 C8 N2 120.8(2) ?
C10 C9 C8 119.8(2) ?
C10 C9 H9A 120.1 ?
C8 C9 H9A 120.1 ?
C9 C10 C11 120.6(2) ?
C9 C10 H10A 119.7 ?
C11 C10 H10A 119.7 ?
C10 C11 C12 119.8(2) ?
C10 C11 H11A 120.1 ?
C12 C11 H11A 120.1 ?
C11 C12 C13 120.4(2) ?
C11 C12 H12A 119.8 ?
C13 C12 H12A 119.8 ?
C12 C13 C8 119.9(2) ?
C12 C13 N3 119.8(2) ?
C8 C13 N3 120.27(19) ?
O4 C14 N3 123.4(2) ?
O4 C14 C15 119.86(19) ?
N3 C14 C15 116.7(2) yes
C20 C15 C16 118.2(2) ?
C20 C15 C14 120.7(2) ?
C16 C15 C14 120.7(2) ?
C17 C16 C15 123.3(2) ?
C17 C16 N4 119.7(2) ?
C15 C16 N4 117.0(2) ?
C18 C17 C16 116.4(2) ?
C18 C17 C22 120.6(2) ?
C16 C17 C22 123.0(2) ?
C19 C18 C17 121.7(2) ?
C19 C18 H18A 119.1 ?
C17 C18 H18A 119.1 ?
C18 C19 C20 120.7(2) ?
C18 C19 H19A 119.7 ?
C20 C19 H19A 119.7 ?
C15 C20 C19 119.8(2) ?
C15 C20 H20A 120.1 ?
C19 C20 H20A 120.1 ?
C2 C21 H21A 109.5 ?
C2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C2 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C17 C22 H22A 109.5 ?
C17 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C17 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.215(4) ?
O2 N1 1.206(3) ?
O3 C7 1.227(3) yes
O4 C14 1.226(3) yes
O5 N4 1.226(3) ?
O6 N4 1.175(3) ?
N1 C1 1.470(4) ?
N2 C7 1.341(3) yes
N2 C8 1.421(3) yes
N2 H2A 0.8600 ?
N3 C13 1.427(3) yes
N3 C14 1.342(3) yes
N3 H3A 0.8600 ?
N4 C16 1.471(3) ?
C1 C6 1.394(3) ?
C1 C2 1.395(4) ?
C2 C3 1.380(5) ?
C2 C21 1.517(4) ?
C3 C4 1.378(5) ?
C3 H3B 0.9300 ?
C4 C5 1.373(4) ?
C4 H4A 0.9300 ?
C5 C6 1.388(3) ?
C5 H5A 0.9300 ?
C6 C7 1.500(3) ?
C8 C13 1.390(3) ?
C8 C9 1.395(3) ?
C9 C10 1.379(4) ?
C9 H9A 0.9300 ?
C10 C11 1.380(4) ?
C10 H10A 0.9300 ?
C11 C12 1.380(4) ?
C11 H11A 0.9300 ?
C12 C13 1.385(3) ?
C12 H12A 0.9300 ?
C14 C15 1.505(3) ?
C15 C20 1.382(3) ?
C15 C16 1.396(3) ?
C16 C17 1.388(3) ?
C17 C18 1.387(4) ?
C17 C22 1.508(4) ?
C18 C19 1.377(4) ?
C18 H18A 0.9300 ?
C19 C20 1.384(3) ?
C19 H19A 0.9300 ?
C20 H20A 0.9300 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
C22 H22A 0.9600 ?
C22 H22B 0.9600 ?
C22 H22C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A O4 2_766 0.86 2.19 3.044(3) 169 yes
N3 H3A O3 2_666 0.86 2.17 2.950(3) 151 yes
C21 H21C O1 1_555 0.96 2.44 2.914(5) 110 yes
C22 H22A O5 1_555 0.96 2.26 2.934(4) 126 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
O2 N1 C1 C6 45.2(3)
O1 N1 C1 C6 -132.2(3)
O2 N1 C1 C2 -133.2(3)
O1 N1 C1 C2 49.4(4)
C6 C1 C2 C3 4.3(4)
N1 C1 C2 C3 -177.4(2)
C6 C1 C2 C21 -172.2(3)
N1 C1 C2 C21 6.1(4)
C1 C2 C3 C4 -1.4(4)
C21 C2 C3 C4 175.2(3)
C2 C3 C4 C5 -2.0(4)
C3 C4 C5 C6 2.7(4)
C4 C5 C6 C1 0.0(3)
C4 C5 C6 C7 176.5(2)
C2 C1 C6 C5 -3.7(4)
N1 C1 C6 C5 178.0(2)
C2 C1 C6 C7 179.9(2)
N1 C1 C6 C7 1.6(3)
C8 N2 C7 O3 -1.1(4)
C8 N2 C7 C6 -178.65(19)
C5 C6 C7 O3 -110.3(3)
C1 C6 C7 O3 66.0(3)
C5 C6 C7 N2 67.3(3)
C1 C6 C7 N2 -116.4(2)
C7 N2 C8 C13 132.6(2)
C7 N2 C8 C9 -48.9(3)
C13 C8 C9 C10 -1.6(3)
N2 C8 C9 C10 179.9(2)
C8 C9 C10 C11 0.0(4)
C9 C10 C11 C12 1.1(4)
C10 C11 C12 C13 -0.6(4)
C11 C12 C13 C8 -1.0(4)
C11 C12 C13 N3 -179.9(2)
C9 C8 C13 C12 2.1(3)
N2 C8 C13 C12 -179.4(2)
C9 C8 C13 N3 -179.0(2)
N2 C8 C13 N3 -0.5(3)
C14 N3 C13 C12 -62.3(3)
C14 N3 C13 C8 118.8(2)
C13 N3 C14 O4 -9.3(3)
C13 N3 C14 C15 171.71(19)
O4 C14 C15 C20 -100.5(3)
N3 C14 C15 C20 78.6(3)
O4 C14 C15 C16 72.3(3)
N3 C14 C15 C16 -108.6(2)
C20 C15 C16 C17 -0.5(3)
C14 C15 C16 C17 -173.4(2)
C20 C15 C16 N4 -179.9(2)
C14 C15 C16 N4 7.2(3)
O6 N4 C16 C17 -130.9(3)
O5 N4 C16 C17 52.7(4)
O6 N4 C16 C15 48.5(4)
O5 N4 C16 C15 -128.0(3)
C15 C16 C17 C18 1.2(3)
N4 C16 C17 C18 -179.5(2)
C15 C16 C17 C22 -177.3(2)
N4 C16 C17 C22 2.1(4)
C16 C17 C18 C19 -1.0(4)
C22 C17 C18 C19 177.5(2)
C17 C18 C19 C20 0.1(4)
C16 C15 C20 C19 -0.4(3)
C14 C15 C20 C19 172.5(2)
C18 C19 C20 C15 0.6(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128151
2 PubChem 71427737
