#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228459.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_2228459
loop_
_publ_author_name
'Ren, Yuehong'
'Zuo, Yu'
'Xiang, Yonggang'
'Zhu, Ruitao'
_publ_section_title
;
 3,5-Dinitro-N-(4-nitrophenyl)benzamide
;
_journal_coeditor_code           LH5155
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3158
_journal_paper_doi               10.1107/S1600536810045915
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H8 N4 O7'
_chemical_formula_moiety         'C13 H8 N4 O7'
_chemical_formula_sum            'C13 H8 N4 O7'
_chemical_formula_weight         332.23
_chemical_name_systematic
;
3,5-Dinitro-N-(4-nitrophenyl)benzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.2850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8999(9)
_cell_length_b                   8.0190(10)
_cell_length_c                   21.111(2)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.431
_cell_measurement_theta_min      2.586
_cell_volume                     1333.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and 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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6462
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0460
_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)+(0.0524P)²+0.2955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1419
_reflns_number_total             2361
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5155.cif
_cod_data_source_block           I
_cod_original_cell_volume        1333.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228459
_cod_database_fobs_code          2228459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 1.4744(2) 0.3431(3) 0.43550(9) 0.0417(6) Uani d . 1 . .
H H1 1.5292 0.3850 0.4056 0.050 Uiso calc R 1 . .
N N2 0.8118(3) 0.6627(3) 0.33003(12) 0.0470(6) Uani d . 1 . .
N N3 1.3396(3) 0.6676(4) 0.22261(10) 0.0503(7) Uani d . 1 . .
N N4 1.8925(3) 0.0058(3) 0.61994(11) 0.0498(7) Uani d . 1 . .
O O1 1.2103(2) 0.3154(3) 0.46823(9) 0.0623(7) Uani d . 1 . .
O O2 0.7337(2) 0.6051(3) 0.37295(10) 0.0605(6) Uani d . 1 . .
O O3 0.7509(3) 0.7558(3) 0.28922(11) 0.0735(8) Uani d . 1 . .
O O4 1.2863(3) 0.7866(3) 0.19062(10) 0.0702(7) Uani d . 1 . .
O O5 1.4673(3) 0.5907(3) 0.21316(9) 0.0737(8) Uani d . 1 . .
O O6 2.0458(3) 0.0098(3) 0.61510(10) 0.0680(7) Uani d . 1 . .
O O7 1.8282(3) -0.0657(4) 0.66238(11) 0.0845(9) Uani d . 1 . .
C C1 1.3044(3) 0.3678(3) 0.43039(12) 0.0381(7) Uani d . 1 . .
C C2 1.2337(3) 0.4698(3) 0.37448(11) 0.0340(6) Uani d . 1 . .
C C3 1.0657(3) 0.5183(3) 0.37588(12) 0.0376(7) Uani d . 1 . .
H H3 1.0034 0.4865 0.4096 0.045 Uiso calc R 1 . .
C C4 0.9913(3) 0.6136(3) 0.32735(12) 0.0362(6) Uani d . 1 . .
C C5 1.0782(3) 0.6669(3) 0.27726(11) 0.0385(7) Uani d . 1 . .
H H5 1.0272 0.7341 0.2454 0.046 Uiso calc R 1 . .
C C6 1.2440(3) 0.6163(3) 0.27634(11) 0.0359(6) Uani d . 1 . .
C C7 1.3229(3) 0.5177(3) 0.32335(11) 0.0374(7) Uani d . 1 . .
H H7 1.4347 0.4837 0.3207 0.045 Uiso calc R 1 . .
C C8 1.5729(3) 0.2579(3) 0.48343(11) 0.0343(6) Uani d . 1 . .
C C9 1.7451(3) 0.2441(4) 0.47600(13) 0.0434(7) Uani d . 1 . .
H H9 1.7894 0.2898 0.4403 0.052 Uiso calc R 1 . .
C C10 1.8513(3) 0.1638(4) 0.52054(12) 0.0441(7) Uani d . 1 . .
H H10 1.9671 0.1561 0.5157 0.053 Uiso calc R 1 . .
C C11 1.7825(3) 0.0952(3) 0.57246(12) 0.0374(7) Uani d . 1 . .
C C12 1.6121(3) 0.1071(4) 0.58118(12) 0.0419(7) Uani d . 1 . .
H H12 1.5688 0.0596 0.6168 0.050 Uiso calc R 1 . .
C C13 1.5060(3) 0.1896(4) 0.53691(11) 0.0413(7) Uani d . 1 . .
H H13 1.3908 0.1997 0.5426 0.050 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C8 . . 128.3(2) ?
C1 N1 H1 . . 115.8 ?
C8 N1 H1 . . 115.8 ?
O3 N2 O2 . . 124.3(2) ?
O3 N2 C4 . . 117.9(2) ?
O2 N2 C4 . . 117.8(2) ?
O5 N3 O4 . . 124.2(2) ?
O5 N3 C6 . . 117.9(3) ?
O4 N3 C6 . . 118.0(3) ?
O7 N4 O6 . . 123.2(2) ?
O7 N4 C11 . . 118.7(2) ?
O6 N4 C11 . . 118.1(2) ?
O1 C1 N1 . . 123.6(2) ?
O1 C1 C2 . . 119.8(2) ?
N1 C1 C2 . . 116.6(2) ?
C3 C2 C7 . . 118.8(2) ?
C3 C2 C1 . . 115.8(2) ?
C7 C2 C1 . . 125.4(2) ?
C4 C3 C2 . . 119.8(2) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C5 C4 C3 . . 122.5(2) ?
C5 C4 N2 . . 119.0(2) ?
C3 C4 N2 . . 118.6(2) ?
C4 C5 C6 . . 116.9(2) ?
C4 C5 H5 . . 121.5 ?
C6 C5 H5 . . 121.5 ?
C5 C6 C7 . . 122.6(2) ?
C5 C6 N3 . . 118.3(2) ?
C7 C6 N3 . . 119.1(2) ?
C6 C7 C2 . . 119.4(2) ?
C6 C7 H7 . . 120.3 ?
C2 C7 H7 . . 120.3 ?
C9 C8 C13 . . 119.7(2) ?
C9 C8 N1 . . 116.9(2) ?
C13 C8 N1 . . 123.4(2) ?
C10 C9 C8 . . 121.0(2) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 118.4(2) ?
C9 C10 H10 . . 120.8 ?
C11 C10 H10 . . 120.8 ?
C10 C11 C12 . . 121.9(2) ?
C10 C11 N4 . . 119.5(2) ?
C12 C11 N4 . . 118.6(2) ?
C11 C12 C13 . . 119.6(2) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C12 C13 C8 . . 119.3(2) ?
C12 C13 H13 . . 120.3 ?
C8 C13 H13 . . 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.354(3) ?
N1 C8 . 1.407(3) ?
N1 H1 . 0.8600 ?
N2 O3 . 1.212(3) ?
N2 O2 . 1.224(3) ?
N2 C4 . 1.476(3) ?
N3 O5 . 1.212(3) ?
N3 O4 . 1.225(3) ?
N3 C6 . 1.467(3) ?
N4 O7 . 1.207(3) ?
N4 O6 . 1.224(3) ?
N4 C11 . 1.464(3) ?
O1 C1 . 1.206(3) ?
C1 C2 . 1.509(3) ?
C2 C3 . 1.386(3) ?
C2 C7 . 1.386(3) ?
C3 C4 . 1.375(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.371(3) ?
C5 C6 . 1.373(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.381(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.385(3) ?
C8 C13 . 1.394(3) ?
C9 C10 . 1.373(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.374(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.376(3) ?
C12 C13 . 1.377(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
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
N1 H1 O2 1_655 0.86 2.52 3.280(3) 147 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 C1 O1 . . . . -0.7(5) ?
C8 N1 C1 C2 . . . . 178.0(2) ?
O1 C1 C2 C3 . . . . 9.6(4) ?
N1 C1 C2 C3 . . . . -169.1(2) ?
O1 C1 C2 C7 . . . . -170.7(3) ?
N1 C1 C2 C7 . . . . 10.6(4) ?
C7 C2 C3 C4 . . . . -0.6(4) ?
C1 C2 C3 C4 . . . . 179.1(2) ?
C2 C3 C4 C5 . . . . -1.4(4) ?
C2 C3 C4 N2 . . . . 179.7(2) ?
O3 N2 C4 C5 . . . . -3.8(4) ?
O2 N2 C4 C5 . . . . 175.4(2) ?
O3 N2 C4 C3 . . . . 175.2(3) ?
O2 N2 C4 C3 . . . . -5.6(4) ?
C3 C4 C5 C6 . . . . 1.9(4) ?
N2 C4 C5 C6 . . . . -179.1(2) ?
C4 C5 C6 C7 . . . . -0.5(4) ?
C4 C5 C6 N3 . . . . 178.5(2) ?
O5 N3 C6 C5 . . . . -161.5(3) ?
O4 N3 C6 C5 . . . . 19.3(4) ?
O5 N3 C6 C7 . . . . 17.5(4) ?
O4 N3 C6 C7 . . . . -161.6(3) ?
C5 C6 C7 C2 . . . . -1.4(4) ?
N3 C6 C7 C2 . . . . 179.6(2) ?
C3 C2 C7 C6 . . . . 2.0(4) ?
C1 C2 C7 C6 . . . . -177.7(2) ?
C1 N1 C8 C9 . . . . 177.2(3) ?
C1 N1 C8 C13 . . . . -3.2(4) ?
C13 C8 C9 C10 . . . . 0.0(4) ?
N1 C8 C9 C10 . . . . 179.6(3) ?
C8 C9 C10 C11 . . . . 0.9(4) ?
C9 C10 C11 C12 . . . . -1.0(4) ?
C9 C10 C11 N4 . . . . 178.7(3) ?
O7 N4 C11 C10 . . . . -173.8(3) ?
O6 N4 C11 C10 . . . . 7.4(4) ?
O7 N4 C11 C12 . . . . 5.8(4) ?
O6 N4 C11 C12 . . . . -173.0(2) ?
C10 C11 C12 C13 . . . . 0.1(4) ?
N4 C11 C12 C13 . . . . -179.6(3) ?
C11 C12 C13 C8 . . . . 0.9(4) ?
C9 C8 C13 C12 . . . . -0.9(4) ?
N1 C8 C13 C12 . . . . 179.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2350334
