#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222530.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_2222530
loop_
_publ_author_name
'Saeed, Aamer'
'Simpson, Jim'
_publ_section_title
;
 N-(2-Nitrophenyl)benzamide
;
_journal_coeditor_code           AT2824
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1845
_journal_paper_doi               10.1107/S1600536809024271
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H10 N2 O3'
_chemical_formula_moiety         'C13 H10 N2 O3'
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23
_chemical_name_systematic
;
N-(2-Nitrophenyl)benzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.560(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2061(5)
_cell_length_b                   7.4253(5)
_cell_length_c                   20.6031(13)
_cell_measurement_reflns_used    4696
_cell_measurement_temperature    89(2)
_cell_measurement_theta_max      31.80
_cell_measurement_theta_min      2.83
_cell_volume                     1100.29(13)
_computing_cell_refinement       'APEX2 and SAINT (Bruker 2006)'
_computing_data_collection       'APEX2 (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al.,
2004), PLATON (Spek, 2009)
and publCIF (Westrip, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson,
1999)
;
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      89(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20195
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         33.33
_diffrn_reflns_theta_min         3.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0629P)²+0.2001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                3098
_reflns_number_total             3948
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2824.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222530
_cod_database_fobs_code          2222530
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.73812(11) 0.03317(11) 0.50049(4) 0.01315(16) Uani d . 1 . .
H H1N 0.678(2) -0.064(2) 0.5129(7) 0.031(4) Uiso d . 1 . .
O O1 0.87401(11) 0.16410(10) 0.41448(4) 0.01879(17) Uani d . 1 . .
C C1 0.78498(13) 0.04075(12) 0.43690(4) 0.01259(17) Uani d . 1 . .
C C2 0.71690(13) -0.11570(12) 0.39614(4) 0.01239(17) Uani d . 1 . .
C C3 0.70064(14) -0.09052(13) 0.32883(5) 0.01564(19) Uani d . 1 . .
H H3 0.7315 0.0226 0.3109 0.019 Uiso calc R 1 . .
C C4 0.63950(14) -0.23021(14) 0.28797(5) 0.01771(19) Uani d . 1 . .
H H4 0.6275 -0.2120 0.2423 0.021 Uiso calc R 1 . .
C C5 0.59588(14) -0.39666(14) 0.31405(5) 0.0176(2) Uani d . 1 . .
H H5 0.5543 -0.4921 0.2861 0.021 Uiso calc R 1 . .
C C6 0.61305(14) -0.42356(13) 0.38095(5) 0.01679(19) Uani d . 1 . .
H H6 0.5840 -0.5376 0.3986 0.020 Uiso calc R 1 . .
C C7 0.67274(13) -0.28349(13) 0.42198(5) 0.01451(18) Uani d . 1 . .
H H7 0.6836 -0.3018 0.4677 0.017 Uiso calc R 1 . .
C C8 0.78625(12) 0.15306(12) 0.55126(4) 0.01171(17) Uani d . 1 . .
C C9 0.78085(13) 0.09917(12) 0.61677(4) 0.01252(17) Uani d . 1 . .
N N2 0.72463(12) -0.08197(11) 0.63520(4) 0.01487(17) Uani d . 1 . .
O O2 0.76511(13) -0.13362(11) 0.69076(4) 0.0268(2) Uani d . 1 . .
O O3 0.63473(11) -0.17725(10) 0.59477(3) 0.01818(16) Uani d . 1 . .
C C10 0.82755(13) 0.21653(14) 0.66792(5) 0.01574(19) Uani d . 1 . .
H H10 0.8235 0.1765 0.7116 0.019 Uiso calc R 1 . .
C C11 0.87973(14) 0.39107(14) 0.65503(5) 0.0184(2) Uani d . 1 . .
H H11 0.9112 0.4720 0.6897 0.022 Uiso calc R 1 . .
C C12 0.88585(14) 0.44738(13) 0.59089(5) 0.01733(19) Uani d . 1 . .
H H12 0.9218 0.5675 0.5820 0.021 Uiso calc R 1 . .
C C13 0.84023(13) 0.33090(12) 0.53965(5) 0.01466(18) Uani d . 1 . .
H H13 0.8457 0.3723 0.4962 0.018 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 . . 128.45(8) ?
C1 N1 H1N . . 117.4(10) ?
C8 N1 H1N . . 113.9(10) ?
O1 C1 N1 . . 123.75(9) ?
O1 C1 C2 . . 121.96(8) ?
N1 C1 C2 . . 114.29(8) ?
C3 C2 C7 . . 119.32(9) ?
C3 C2 C1 . . 117.20(8) ?
C7 C2 C1 . . 123.47(8) ?
C4 C3 C2 . . 120.34(9) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 119.97(9) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 120.13(9) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 119.99(9) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C6 C7 C2 . . 120.23(9) ?
C6 C7 H7 . . 119.9 ?
C2 C7 H7 . . 119.9 ?
N1 C8 C13 . . 122.01(8) ?
N1 C8 C9 . . 120.93(8) ?
C13 C8 C9 . . 117.06(8) ?
C10 C9 C8 . . 121.79(9) ?
C10 C9 N2 . . 115.92(8) ?
C8 C9 N2 . . 122.29(8) ?
O2 N2 O3 . . 122.11(9) ?
O2 N2 C9 . . 118.49(8) ?
O3 N2 C9 . . 119.38(8) ?
C11 C10 C9 . . 119.87(9) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C12 . . 119.39(9) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C13 C12 C11 . . 121.05(9) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C8 . . 120.83(9) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
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 . 1.3742(11) ?
N1 C8 . 1.4006(12) ?
N1 H1N . 0.887(16) ?
O1 C1 . 1.2250(11) ?
C1 C2 . 1.4981(13) ?
C2 C3 . 1.3971(12) ?
C2 C7 . 1.3992(13) ?
C3 C4 . 1.3902(14) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3915(15) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3906(14) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.3914(13) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C13 . 1.4014(13) ?
C8 C9 . 1.4107(13) ?
C9 C10 . 1.3925(13) ?
C9 N2 . 1.4617(12) ?
N2 O2 . 1.2251(10) ?
N2 O3 . 1.2439(11) ?
C10 C11 . 1.3799(14) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3893(15) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.3883(13) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
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
N1 H1N O3 . 0.887(16) 1.927(15) 2.6361(11) 135.7(13)
C10 H10 O2 2_656 0.95 2.57 3.2254(12) 126.4
C6 H6 O3 3_646 0.95 2.65 3.5122(12) 151.4
C12 H12 O1 3_766 0.95 2.48 3.3695(12) 156.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 62968
