#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/36/2233609.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_2233609
loop_
_publ_author_name
'Win, Yip-Foo'
'Choong, Chen-Shang'
'Teoh, Siang-Guan'
'Quah, Ching Kheng'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-3-nitrobenzoic acid
;
_journal_coeditor_code           QM2050
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o488
_journal_paper_doi               10.1107/S1600536812002036
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H6 N2 O4'
_chemical_formula_moiety         'C7 H6 N2 O4'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14
_chemical_name_systematic
;
2-Amino-3-nitrobenzoic acid
;
_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                 92.1140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0231(3)
_cell_length_b                   7.4338(2)
_cell_length_c                   11.0392(4)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100
_cell_measurement_theta_max      34.83
_cell_measurement_theta_min      2.86
_cell_volume                     739.96(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22297
_diffrn_reflns_theta_full        35.01
_diffrn_reflns_theta_max         35.01
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.9555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0662P)²+0.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2707
_reflns_number_total             3247
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2050.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233609
_cod_database_fobs_code          2233609
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_symmetry_multiplicity
O O1 1.00882(10) 0.85440(11) 0.40698(8) 0.03096(19) Uani d . 1 1
O O2 0.99701(8) 0.61460(10) 0.29827(6) 0.02030(14) Uani d . 1 1
O O3 0.62645(7) 0.11784(9) 0.43650(6) 0.01909(14) Uani d . 1 1
O O4 0.51199(8) 0.18983(10) 0.60595(6) 0.01981(14) Uani d . 1 1
N N1 0.95660(8) 0.70510(10) 0.38522(6) 0.01587(14) Uani d . 1 1
N N2 0.81247(9) 0.35687(11) 0.34730(7) 0.01954(16) Uani d . 1 1
C C1 0.64687(9) 0.51128(12) 0.62950(7) 0.01552(15) Uani d . 1 1
H H1A 0.5784 0.4697 0.6865 0.019 Uiso calc R 1 1
C C2 0.71159(10) 0.67982(12) 0.64617(8) 0.01749(16) Uani d . 1 1
H H2A 0.6870 0.7528 0.7131 0.021 Uiso calc R 1 1
C C3 0.81229(9) 0.73922(12) 0.56356(7) 0.01620(15) Uani d . 1 1
H H3A 0.8579 0.8536 0.5742 0.019 Uiso calc R 1 1
C C4 0.84738(9) 0.63239(11) 0.46482(7) 0.01390(14) Uani d . 1 1
C C5 0.78217(8) 0.45981(11) 0.44292(7) 0.01334(14) Uani d . 1 1
C C6 0.67970(9) 0.40152(11) 0.53140(7) 0.01354(14) Uani d . 1 1
C C7 0.60572(9) 0.22530(11) 0.51976(7) 0.01458(15) Uani d . 1 1
H H1N2 0.8797(19) 0.393(2) 0.2953(15) 0.034(4) Uiso d . 1 1
H H2N2 0.7714(18) 0.251(2) 0.3400(14) 0.033(4) Uiso d . 1 1
H H1O4 0.471(2) 0.092(3) 0.5901(16) 0.044(5) Uiso 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
C7 O4 H1O4 108.3(12)
O1 N1 O2 121.45(7)
O1 N1 C4 118.94(7)
O2 N1 C4 119.59(7)
C5 N2 H1N2 119.8(11)
C5 N2 H2N2 119.3(10)
H1N2 N2 H2N2 120.7(15)
C2 C1 C6 121.91(7)
C2 C1 H1A 119.0
C6 C1 H1A 119.0
C3 C2 C1 118.87(8)
C3 C2 H2A 120.6
C1 C2 H2A 120.6
C2 C3 C4 120.47(8)
C2 C3 H3A 119.8
C4 C3 H3A 119.8
C3 C4 C5 122.67(7)
C3 C4 N1 116.15(7)
C5 C4 N1 121.17(7)
N2 C5 C4 123.47(7)
N2 C5 C6 121.24(7)
C4 C5 C6 115.30(7)
C1 C6 C5 120.75(7)
C1 C6 C7 118.60(7)
C5 C6 C7 120.64(7)
O3 C7 O4 121.60(8)
O3 C7 C6 123.94(7)
O4 C7 C6 114.46(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2260(10)
O2 N1 1.2380(10)
O3 C7 1.2371(10)
O4 C7 1.3227(10)
O4 H1O4 0.83(2)
N1 C4 1.4490(10)
N2 C5 1.3401(11)
N2 H1N2 0.893(17)
N2 H2N2 0.875(18)
C1 C2 1.3916(12)
C1 C6 1.3964(11)
C1 H1A 0.9500
C2 C3 1.3832(12)
C2 H2A 0.9500
C3 C4 1.3945(11)
C3 H3A 0.9500
C4 C5 1.4283(11)
C5 C6 1.4364(11)
C6 C7 1.4737(11)
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 H1N2 O2 . 0.892(17) 1.958(16) 2.6082(11) 128.5(13) yes
N2 H1N2 O1 2_745 0.892(17) 2.499(17) 3.2885(12) 147.8(14) yes
N2 H2N2 O3 . 0.872(15) 1.982(16) 2.6582(10) 133.4(14) yes
O4 H1O4 O3 3_656 0.83(2) 1.81(2) 2.6397(10) 176.2(17) yes
C3 H3A O1 3_776 0.9500 2.4900 3.4349(12) 176.00 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
C6 C1 C2 C3 -0.58(13)
C1 C2 C3 C4 0.47(13)
C2 C3 C4 C5 0.49(13)
C2 C3 C4 N1 -178.63(8)
O1 N1 C4 C3 -1.42(12)
O2 N1 C4 C3 177.38(7)
O1 N1 C4 C5 179.46(8)
O2 N1 C4 C5 -1.75(12)
C3 C4 C5 N2 178.69(8)
N1 C4 C5 N2 -2.24(13)
C3 C4 C5 C6 -1.28(12)
N1 C4 C5 C6 177.80(7)
C2 C1 C6 C5 -0.28(13)
C2 C1 C6 C7 -179.61(8)
N2 C5 C6 C1 -178.81(8)
C4 C5 C6 C1 1.16(11)
N2 C5 C6 C7 0.50(13)
C4 C5 C6 C7 -179.53(7)
C1 C6 C7 O3 179.89(8)
C5 C6 C7 O3 0.55(13)
C1 C6 C7 O4 0.60(11)
C5 C6 C7 O4 -178.73(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 190402
