#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/21/2232130.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_2232130
loop_
_publ_author_name
'Johnston, Dean H.'
'Taylor, Colin R.'
_publ_section_title
;
 4-Nitro-N-(3-nitrophenyl)benzamide
;
_journal_coeditor_code           ZL2389
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2735
_journal_paper_doi               10.1107/S1600536811038062
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H9 N3 O5'
_chemical_formula_moiety         'C13 H9 N3 O5'
_chemical_formula_sum            'C13 H9 N3 O5'
_chemical_formula_weight         287.23
_chemical_melting_point          502
_chemical_name_common            4-nitro-N-(3-nitrophenyl)benzamide
_chemical_name_systematic
;
4-Nitro-N-(3-nitrophenyl)benzamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2011.4-1'
_cell_angle_alpha                90
_cell_angle_beta                 90.294(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8878(6)
_cell_length_b                   21.686(3)
_cell_length_c                   7.3919(11)
_cell_measurement_reflns_used    1373
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      24.5699
_cell_measurement_theta_min      2.7556
_cell_volume                     623.21(16)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 and GIS (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
PLATON (Spek, 2009), Mercury (Macrae et al., 2008), and
POV-Ray (Cason,
2004)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3940
_diffrn_reflns_theta_full        25.13
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1136
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0339
_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)+(0.0460P)²+0.0480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                1008
_reflns_number_total             1136
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            zl2389.cif
_cod_data_source_block           I
_cod_original_cell_volume        623.20(16)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2232130
_cod_database_fobs_code          2232130
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_symmetry_multiplicity
C C1 0.5757(8) 0.50143(14) 0.7761(4) 0.0293(7) Uani d . 1 1
C C2 0.4065(8) 0.55485(16) 0.8360(4) 0.0342(8) Uani d . 1 1
H H2 0.3754 0.5616 0.9618 0.041 Uiso calc R 1 1
C C3 0.2833(8) 0.59829(15) 0.7109(4) 0.0335(7) Uani d . 1 1
H H3 0.1647 0.6342 0.7499 0.040 Uiso calc R 1 1
C C4 0.3402(8) 0.58731(15) 0.5270(4) 0.0305(7) Uani d . 1 1
C C5 0.5099(8) 0.53518(14) 0.4631(4) 0.0324(7) Uani d . 1 1
H H5 0.5439 0.5292 0.3372 0.039 Uiso calc R 1 1
C C6 0.6291(8) 0.49190(14) 0.5889(4) 0.0310(7) Uani d . 1 1
H H6 0.7462 0.4560 0.5487 0.037 Uiso calc R 1 1
N N1 0.2079(8) 0.63348(12) 0.3938(4) 0.0376(7) Uani d . 1 1
O O1 0.3012(8) 0.62833(13) 0.2344(3) 0.0634(9) Uani d . 1 1
O O2 0.0141(7) 0.67441(11) 0.4478(3) 0.0505(7) Uani d . 1 1
C C7 0.7131(8) 0.45847(15) 0.9221(4) 0.0331(7) Uani d . 1 1
O O3 0.7597(8) 0.47773(12) 1.0776(3) 0.0533(7) Uani d . 1 1
N N2 0.7873(7) 0.39887(12) 0.8706(3) 0.0333(6) Uani d . 1 1
H H2N 0.7336 0.3889 0.7585 0.040 Uiso calc R 1 1
C C8 0.9407(8) 0.35147(14) 0.9776(4) 0.0288(7) Uani d . 1 1
C C9 1.0551(8) 0.36141(15) 1.1561(4) 0.0300(7) Uani d . 1 1
H H9 1.0295 0.4004 1.2133 0.036 Uiso calc R 1 1
C C10 1.2070(8) 0.31193(15) 1.2457(4) 0.0293(7) Uani d . 1 1
C C11 1.2552(8) 0.25372(14) 1.1709(4) 0.0317(7) Uani d . 1 1
H H11 1.3622 0.2214 1.2371 0.038 Uiso calc R 1 1
C C12 1.1382(9) 0.24514(16) 0.9931(4) 0.0352(8) Uani d . 1 1
H H12 1.1654 0.2061 0.9368 0.042 Uiso calc R 1 1
C C13 0.9830(8) 0.29302(14) 0.8981(4) 0.0318(7) Uani d . 1 1
H H13 0.9045 0.2862 0.7778 0.038 Uiso calc R 1 1
N N3 1.3347(7) 0.32240(13) 1.4340(3) 0.0344(6) Uani d . 1 1
O O4 1.2424(7) 0.36973(11) 1.5145(3) 0.0508(7) Uani d . 1 1
O O5 1.5281(7) 0.28377(13) 1.5016(3) 0.0543(8) Uani d . 1 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
C2 C1 C6 120.0(3)
C2 C1 C7 116.4(2)
C6 C1 C7 123.5(3)
C3 C2 C1 120.3(3)
C3 C2 H2 119.8
C1 C2 H2 119.8
C4 C3 C2 118.1(3)
C4 C3 H3 120.9
C2 C3 H3 120.9
C5 C4 C3 123.0(3)
C5 C4 N1 118.9(2)
C3 C4 N1 118.1(3)
C4 C5 C6 118.4(3)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 C1 120.2(3)
C5 C6 H6 119.9
C1 C6 H6 119.9
O2 N1 O1 123.7(3)
O2 N1 C4 118.6(3)
O1 N1 C4 117.7(3)
O3 C7 N2 123.0(3)
O3 C7 C1 120.2(3)
N2 C7 C1 116.8(3)
C7 N2 C8 127.6(3)
C7 N2 H2N 116.2
C8 N2 H2N 116.2
C13 C8 C9 119.5(3)
C13 C8 N2 117.9(2)
C9 C8 N2 122.6(3)
C10 C9 C8 117.4(3)
C10 C9 H9 121.3
C8 C9 H9 121.3
C9 C10 C11 124.7(2)
C9 C10 N3 117.7(3)
C11 C10 N3 117.6(3)
C10 C11 C12 116.7(3)
C10 C11 H11 121.6
C12 C11 H11 121.6
C13 C12 C11 120.9(3)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C8 120.9(3)
C12 C13 H13 119.6
C8 C13 H13 119.6
O5 N3 O4 123.1(3)
O5 N3 C10 118.4(3)
O4 N3 C10 118.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.405(5)
C1 C6 1.415(4)
C1 C7 1.520(4)
C2 C3 1.403(4)
C2 H2 0.9500
C3 C4 1.399(4)
C3 H3 0.9500
C4 C5 1.393(4)
C4 N1 1.494(4)
C5 C6 1.398(4)
C5 H5 0.9500
C6 H6 0.9500
N1 O2 1.232(4)
N1 O1 1.240(4)
C7 O3 1.235(4)
C7 N2 1.378(4)
N2 C8 1.426(4)
N2 H2N 0.8800
C8 C13 1.407(4)
C8 C9 1.407(4)
C9 C10 1.391(4)
C9 H9 0.9500
C10 C11 1.391(4)
C10 N3 1.493(4)
C11 C12 1.401(4)
C11 H11 0.9500
C12 C13 1.390(4)
C12 H12 0.9500
C13 H13 0.9500
N3 O5 1.230(3)
N3 O4 1.240(4)
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
C2 H2 O1 1_556 0.95 2.50 3.375(4) 153.4
C5 H5 O3 1_554 0.95 2.38 3.263(4) 155.1
C13 H13 O5 1_454 0.95 2.51 3.421(4) 161.6
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
C6 C1 C2 C3 1.4(4)
C7 C1 C2 C3 177.5(3)
C1 C2 C3 C4 -1.2(5)
C2 C3 C4 C5 0.6(5)
C2 C3 C4 N1 179.8(3)
C3 C4 C5 C6 -0.1(5)
N1 C4 C5 C6 -179.3(3)
C4 C5 C6 C1 0.2(5)
C2 C1 C6 C5 -0.8(5)
C7 C1 C6 C5 -176.7(3)
C5 C4 N1 O2 169.1(3)
C3 C4 N1 O2 -10.1(4)
C5 C4 N1 O1 -11.0(4)
C3 C4 N1 O1 169.8(3)
C2 C1 C7 O3 -19.7(5)
C6 C1 C7 O3 156.3(3)
C2 C1 C7 N2 161.6(3)
C6 C1 C7 N2 -22.4(4)
O3 C7 N2 C8 -3.5(5)
C1 C7 N2 C8 175.1(3)
C7 N2 C8 C13 178.0(3)
C7 N2 C8 C9 -3.1(5)
C13 C8 C9 C10 0.1(4)
N2 C8 C9 C10 -178.7(3)
C8 C9 C10 C11 0.4(4)
C8 C9 C10 N3 178.9(3)
C9 C10 C11 C12 -0.5(4)
N3 C10 C11 C12 -179.0(3)
C10 C11 C12 C13 0.2(5)
C11 C12 C13 C8 0.3(5)
C9 C8 C13 C12 -0.4(5)
N2 C8 C13 C12 178.4(3)
C9 C10 N3 O5 -165.8(3)
C11 C10 N3 O5 12.8(4)
C9 C10 N3 O4 13.9(4)
C11 C10 N3 O4 -167.5(3)
