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#$Date: 2022-03-29 11:07:42 +0300 (Tue, 29 Mar 2022) $
#$Revision: 274072 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104918.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_8104918
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 3-ammonio-4-aminobenzoate, C7H8N2O2 -- a
 second polymorph
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              187
_journal_page_last               188
_journal_paper_doi               10.1515/ncrs-2020-0510
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C7 H8 N2 O2'
_chemical_formula_sum            'C7 H8 N2 O2'
_chemical_formula_weight         152.15
_chemical_name_common            3-ammonio-4-aminobenzoate
_chemical_name_systematic        3-ammonio-4-aminobenzoate
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.400(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9884(6)
_cell_length_b                   6.0490(4)
_cell_length_c                   12.1290(8)
_cell_measurement_reflns_used    2675
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.70
_cell_volume                     656.54(8)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.8087
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5578
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.061
_diffrn_reflns_theta_min         2.703
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8087
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       platelet
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.351
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0535P)²+0.2213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1295
_reflns_number_total             1571
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0510_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8104918
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_iucr_geom_bonds_special_details
;                                                              
Cg(1) is the centroid of carbon atoms C2--C7.            
;
loop_
_space_group_symop_operation_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85407(10) 0.41707(15) -0.11063(7) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.77074(10) 0.08228(15) -0.07068(8) 0.0261(2) Uani 1 1 d . . . . .
N1 N 0.37216(11) 0.25979(18) 0.18943(9) 0.0199(2) Uani 1 1 d . . . . .
H711 H 0.3488(18) 0.140(3) 0.1459(14) 0.032(4) Uiso 1 1 d . . . . .
H712 H 0.291(2) 0.361(3) 0.1745(14) 0.039(5) Uiso 1 1 d . . . . .
H713 H 0.374(2) 0.210(3) 0.2691(16) 0.047(5) Uiso 1 1 d . . . . .
N2 N 0.47055(12) 0.66069(19) 0.29016(9) 0.0236(3) Uani 1 1 d . . . . .
H721 H 0.4261(19) 0.567(3) 0.3337(14) 0.035(5) Uiso 1 1 d . . . . .
H722 H 0.5114(19) 0.781(3) 0.3234(14) 0.035(4) Uiso 1 1 d . . . . .
C1 C 0.78346(13) 0.2857(2) -0.05217(10) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.70840(13) 0.38375(19) 0.04149(9) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.58797(12) 0.27305(19) 0.08042(9) 0.0173(3) Uani 1 1 d . . . . .
H3 H 0.560296 0.131288 0.051671 0.021 Uiso 1 1 calc R U . . .
C4 C 0.50862(12) 0.36681(19) 0.16011(9) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.55061(13) 0.56941(19) 0.20983(10) 0.0173(3) Uani 1 1 d . . . . .
C6 C 0.67177(13) 0.6802(2) 0.16978(10) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.702408 0.819034 0.200751 0.023 Uiso 1 1 calc R U . . .
C7 C 0.74743(13) 0.5910(2) 0.08603(10) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.826778 0.671634 0.058525 0.023 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N1 H711 111.4(10) . .
C4 N1 H712 108.2(10) . .
H711 N1 H712 105.8(15) . .
C4 N1 H713 115.2(11) . .
H711 N1 H713 107.4(15) . .
H712 N1 H713 108.5(15) . .
C5 N2 H721 117.2(11) . .
C5 N2 H722 115.2(11) . .
H721 N2 H722 115.8(15) . .
O2 C1 O1 123.66(11) . .
O2 C1 C2 118.97(11) . .
O1 C1 C2 117.35(11) . .
C3 C2 C7 118.39(10) . .
C3 C2 C1 119.15(10) . .
C7 C2 C1 122.29(10) . .
C4 C3 C2 120.71(11) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 121.74(10) . .
C3 C4 N1 119.41(10) . .
C5 C4 N1 118.76(10) . .
N2 C5 C4 121.09(11) . .
N2 C5 C6 121.76(11) . .
C4 C5 C6 117.05(10) . .
C7 C6 C5 121.24(11) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C6 C7 C2 120.73(11) . .
C6 C7 H7 119.6 . .
C2 C7 H7 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2734(14) .
O2 C1 1.2543(15) .
N1 C4 1.4602(14) .
N1 H711 0.911(18) .
N1 H712 0.958(19) .
N1 H713 1.01(2) .
N2 C5 1.3798(15) .
N2 H721 0.893(18) .
N2 H722 0.895(19) .
C1 C2 1.4971(16) .
C2 C3 1.3926(15) .
C2 C7 1.3968(16) .
C3 C4 1.3764(15) .
C3 H3 0.9500 .
C4 C5 1.4018(16) .
C5 C6 1.4039(16) .
C6 C7 1.3841(16) .
C6 H6 0.9500 .
C7 H7 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H711 O2 0.911(18) 1.898(19) 2.7673(14) 158.6(15) 3_655
N1 H712 O1 0.958(19) 1.98(2) 2.9160(15) 166.4(15) 3_665
N1 H713 O1 1.01(2) 1.67(2) 2.6694(14) 167.6(18) 4_566
N2 H721 O2 0.893(18) 2.102(18) 2.9674(15) 163.0(16) 4_566
N2 H722 O1 0.895(19) 2.487(17) 3.0504(14) 121.4(13) 4_576
C6 H6 <i>C<i>~g~(1) 0.95 2.66 3.4370(13) 139 2_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 C1 C2 C3 -22.16(17) . . . .
O1 C1 C2 C3 156.09(11) . . . .
O2 C1 C2 C7 162.80(11) . . . .
O1 C1 C2 C7 -18.96(17) . . . .
C7 C2 C3 C4 0.60(17) . . . .
C1 C2 C3 C4 -174.64(11) . . . .
C2 C3 C4 C5 -3.90(18) . . . .
C2 C3 C4 N1 172.50(11) . . . .
C3 C4 C5 N2 -179.56(11) . . . .
N1 C4 C5 N2 4.02(17) . . . .
C3 C4 C5 C6 4.01(17) . . . .
N1 C4 C5 C6 -172.41(10) . . . .
N2 C5 C6 C7 -177.35(11) . . . .
C4 C5 C6 C7 -0.94(17) . . . .
C5 C6 C7 C2 -2.24(18) . . . .
C3 C2 C7 C6 2.42(18) . . . .
C1 C2 C7 C6 177.51(11) . . . .
