#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/47/2234759.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_2234759
loop_
_publ_author_name
'Zhao, Qun'
_publ_section_title
;
 2-Hydroxyanilinium 3,5-dinitrobenzoate
;
_journal_coeditor_code           QK2032
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1535
_journal_paper_doi               10.1107/S1600536812014973
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H8 N O +, C7 H3 N2 O6 -'
_chemical_formula_moiety         'C6 H8 N O +, C7 H3 N2 O6 -'
_chemical_formula_sum            'C13 H11 N3 O7'
_chemical_formula_weight         321.25
_chemical_name_systematic
;
2-Hydroxyanilinium 3,5-dinitrobenzoate
;
_space_group_IT_number           4
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4988(19)
_cell_length_b                   6.0803(12)
_cell_length_c                   12.109(2)
_cell_measurement_reflns_used    7134
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      3.38
_cell_measurement_theta_min      27.47
_cell_volume                     696.5(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       'ω and φ'
_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  0.0982
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7134
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.283
_refine_ls_extinction_coef       0.072(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²\\l³/sin(2\\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0835
_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/[\\s²(Fo²)+(0.0791P)²+1.2502P] where
 P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2176
_reflns_number_gt                1209
_reflns_number_total             1733
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            qk2032.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2234759
_cod_database_fobs_code          2234759
loop_
_symmetry_equiv_pos_as_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 0.3248(7) 0.2505(12) -0.2268(6) 0.0325(16) Uani d . 1 1
C C2 0.2992(7) 0.1113(12) -0.1273(6) 0.0314(16) Uani d . 1 1
C C3 0.2233(7) -0.0841(11) -0.1380(5) 0.0294(15) Uani d . 1 1
H H1 0.1912 -0.1357 -0.2082 0.035 Uiso calc R 1 1
C C4 0.1951(8) -0.2021(12) -0.0450(6) 0.0323(16) Uani d . 1 1
C C5 0.2459(8) -0.1379(13) 0.0596(6) 0.0349(16) Uani d . 1 1
H H2 0.2290 -0.2195 0.1220 0.042 Uiso calc R 1 1
C C6 0.3243(7) 0.0559(13) 0.0675(5) 0.0320(16) Uani d . 1 1
C C7 0.3495(7) 0.1844(12) -0.0223(5) 0.0309(15) Uani d . 1 1
H H3 0.3988 0.3162 -0.0129 0.037 Uiso calc R 1 1
N N1 0.1063(7) -0.3963(12) -0.0578(6) 0.0427(16) Uani d . 1 1
O O1 0.3190(6) 0.1545(8) -0.3201(4) 0.0413(14) Uani d . 1 1
O O2 0.3450(7) 0.4499(9) -0.2114(5) 0.0498(15) Uani d . 1 1
O O3 0.0399(7) -0.4290(12) -0.1476(5) 0.0618(19) Uani d . 1 1
O O4 0.1028(7) -0.5164(11) 0.0228(6) 0.0597(18) Uani d . 1 1
N N2 0.3724(7) 0.1352(13) 0.1794(5) 0.0453(18) Uani d . 1 1
O O5 0.4282(7) 0.3173(11) 0.1871(5) 0.0571(17) Uani d . 1 1
O O6 0.3546(8) 0.0204(12) 0.2592(4) 0.063(2) Uani d . 1 1
C C8 0.2779(8) 0.4903(13) 0.4615(6) 0.0352(17) Uani d . 1 1
C C9 0.1846(9) 0.4540(16) 0.3689(6) 0.047(2) Uani d . 1 1
H H4 0.1890 0.3219 0.3306 0.056 Uiso calc R 1 1
C C10 0.0863(9) 0.6070(18) 0.3322(7) 0.054(2) Uani d . 1 1
H H5 0.0272 0.5818 0.2679 0.064 Uiso calc R 1 1
C C11 0.0747(9) 0.8013(17) 0.3917(7) 0.051(2) Uani d . 1 1
H H6 0.0045 0.9026 0.3691 0.062 Uiso calc R 1 1
C C12 0.1687(8) 0.8452(15) 0.4857(6) 0.0425(18) Uani d . 1 1
H H7 0.1630 0.9760 0.5248 0.051 Uiso calc R 1 1
C C13 0.2689(7) 0.6899(13) 0.5182(6) 0.0326(15) Uani d . 1 1
O O7 0.3797(6) 0.3374(10) 0.4957(4) 0.0444(14) Uani d . 1 1
H H8 0.3601 0.2810 0.5539 0.067 Uiso calc R 1 1
N N3 0.3724(6) 0.7298(10) 0.6120(5) 0.0339(14) Uani d . 1 1
H H9 0.3537 0.8575 0.6435 0.051 Uiso calc R 1 1
H H10 0.4585 0.7345 0.5887 0.051 Uiso calc R 1 1
H H11 0.3683 0.6219 0.6613 0.051 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
O2 C1 O1 125.2(7)
O2 C1 C2 117.6(7)
O1 C1 C2 117.1(6)
C7 C2 C3 119.4(6)
C7 C2 C1 118.9(6)
C3 C2 C1 121.6(6)
C4 C3 C2 120.3(6)
C4 C3 H1 119.9
C2 C3 H1 119.9
C5 C4 C3 121.8(7)
C5 C4 N1 118.9(6)
C3 C4 N1 119.2(6)
C4 C5 C6 116.4(6)
C4 C5 H2 121.8
C6 C5 H2 121.8
C7 C6 C5 123.8(6)
C7 C6 N2 118.6(7)
C5 C6 N2 117.3(6)
C6 C7 C2 118.1(7)
C6 C7 H3 121.0
C2 C7 H3 121.0
O4 N1 O3 124.3(7)
O4 N1 C4 117.3(7)
O3 N1 C4 118.4(7)
O6 N2 O5 123.2(7)
O6 N2 C6 119.3(7)
O5 N2 C6 117.5(7)
O7 C8 C9 121.1(7)
O7 C8 C13 120.6(6)
C9 C8 C13 118.2(8)
C10 C9 C8 121.6(8)
C10 C9 H4 119.2
C8 C9 H4 119.2
C9 C10 C11 119.6(7)
C9 C10 H5 120.2
C11 C10 H5 120.2
C10 C11 C12 120.3(8)
C10 C11 H6 119.8
C12 C11 H6 119.8
C13 C12 C11 118.3(8)
C13 C12 H7 120.8
C11 C12 H7 120.8
C12 C13 C8 121.8(7)
C12 C13 N3 120.8(7)
C8 C13 N3 117.5(6)
C8 O7 H8 109.5
C13 N3 H9 109.5
C13 N3 H10 109.5
H9 N3 H10 109.5
C13 N3 H11 109.5
H9 N3 H11 109.5
H10 N3 H11 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.239(9)
C1 O1 1.269(8)
C1 C2 1.510(10)
C2 C7 1.390(9)
C2 C3 1.390(10)
C3 C4 1.383(9)
C3 H1 0.9300
C4 C5 1.370(10)
C4 N1 1.451(10)
C5 C6 1.393(11)
C5 H2 0.9300
C6 C7 1.377(9)
C6 N2 1.472(9)
C7 H3 0.9300
N1 O4 1.222(9)
N1 O3 1.223(9)
N2 O6 1.216(9)
N2 O5 1.228(10)
C8 O7 1.378(9)
C8 C9 1.382(10)
C8 C13 1.401(10)
C9 C10 1.364(14)
C9 H4 0.9300
C10 C11 1.393(14)
C10 H5 0.9300
C11 C12 1.407(11)
C11 H6 0.9300
C12 C13 1.373(11)
C12 H7 0.9300
C13 N3 1.453(9)
O7 H8 0.8200
N3 H9 0.8900
N3 H10 0.8900
N3 H11 0.8900
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
O7 H8 O1 1_556 0.82 1.78 2.603(7) 179.1
N3 H9 O1 1_566 0.89 1.90 2.771(8) 167.6
N3 H10 O7 2_656 0.89 2.02 2.870(8) 159.0
N3 H11 O2 1_556 0.89 1.89 2.763(8) 165.7
C12 H7 O1 1_566 0.93 2.53 3.240(9) 133.5
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 C1 C2 C7 -23.9(10)
O1 C1 C2 C7 158.5(6)
O2 C1 C2 C3 154.2(7)
O1 C1 C2 C3 -23.4(10)
C7 C2 C3 C4 1.5(10)
C1 C2 C3 C4 -176.6(6)
C2 C3 C4 C5 -3.2(11)
C2 C3 C4 N1 175.2(6)
C3 C4 C5 C6 1.7(10)
N1 C4 C5 C6 -176.7(6)
C4 C5 C6 C7 1.4(10)
C4 C5 C6 N2 176.3(6)
C5 C6 C7 C2 -3.0(10)
N2 C6 C7 C2 -177.8(6)
C3 C2 C7 C6 1.4(10)
C1 C2 C7 C6 179.6(6)
C5 C4 N1 O4 -13.4(10)
C3 C4 N1 O4 168.1(7)
C5 C4 N1 O3 166.3(7)
C3 C4 N1 O3 -12.2(10)
C7 C6 N2 O6 -177.8(7)
C5 C6 N2 O6 7.0(10)
C7 C6 N2 O5 2.8(10)
C5 C6 N2 O5 -172.4(7)
O7 C8 C9 C10 -178.0(8)
C13 C8 C9 C10 0.3(12)
C8 C9 C10 C11 -2.8(13)
C9 C10 C11 C12 3.3(13)
C10 C11 C12 C13 -1.5(12)
C11 C12 C13 C8 -1.0(11)
C11 C12 C13 N3 177.6(7)
O7 C8 C13 C12 179.9(7)
C9 C8 C13 C12 1.6(11)
O7 C8 C13 N3 1.3(9)
C9 C8 C13 N3 -177.0(7)
