#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/42/2224202.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_2224202
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Kennedy, Alan R.'
'Gilmour, Denise'
'De Almeida Santos, R. H.'
'Viana, Rommel B.'
_publ_section_title
;
 Imidazolium 4-aminobenzoate
;
_journal_coeditor_code           FJ2253
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3044
_journal_page_last               o3045
_journal_paper_doi               10.1107/S160053680904625X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C3 H5 N2 +, C7 H6 N O2 -'
_chemical_formula_moiety         'C3 H5 N2 +, C7 H6 N O2 -'
_chemical_formula_sum            'C10 H11 N3 O2'
_chemical_formula_weight         205.22
_chemical_melting_point          443.0(10)
_chemical_name_systematic
;
Imidazolium 4-aminobenzoate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.223(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2038(5)
_cell_length_b                   11.6812(6)
_cell_length_c                   12.0152(6)
_cell_measurement_reflns_used    3056
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.86
_cell_measurement_theta_min      2.47
_cell_volume                     975.59(10)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_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  0.049
_diffrn_reflns_av_sigmaI/netI    0.052
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8533
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis CCD; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.358
_refine_ls_extinction_coef       0.213(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0475
_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)+(0.0670P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                1700
_reflns_number_total             2360
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2253.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224202
_cod_database_fobs_code          2224202
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
O O1 0.13700(14) 0.80374(8) 0.58020(7) 0.0227(3) Uani d . 1 . .
O O2 0.27846(15) 0.96304(8) 0.54056(8) 0.0243(3) Uani d . 1 . .
N N1 0.2159(2) 0.68622(11) 0.07332(10) 0.0247(3) Uani d . 1 . .
N N2 0.77001(18) 0.91059(11) 0.13156(10) 0.0246(3) Uani d . 1 . .
N N3 0.84977(17) 1.06234(10) 0.23605(10) 0.0231(3) Uani d . 1 . .
C C1 0.2104(2) 0.86668(12) 0.51343(11) 0.0201(3) Uani d . 1 . .
C C2 0.21134(19) 0.81695(11) 0.39852(10) 0.0187(3) Uani d . 1 . .
C C3 0.3206(2) 0.86798(12) 0.33249(11) 0.0218(3) Uani d . 1 . .
H H3 0.3954 0.9338 0.3613 0.026 Uiso calc R 1 . .
C C4 0.3225(2) 0.82474(12) 0.22568(11) 0.0222(3) Uani d . 1 . .
H H4 0.3975 0.8615 0.1819 0.027 Uiso calc R 1 . .
C C5 0.2148(2) 0.72728(12) 0.18135(11) 0.0206(3) Uani d . 1 . .
C C6 0.1034(2) 0.67656(11) 0.24708(11) 0.0212(3) Uani d . 1 . .
H H6 0.0274 0.6112 0.2181 0.025 Uiso calc R 1 . .
C C7 0.10240(19) 0.72053(11) 0.35398(11) 0.0204(3) Uani d . 1 . .
H H7 0.0265 0.6845 0.3977 0.025 Uiso calc R 1 . .
C C8 0.7922(2) 0.95506(12) 0.23596(12) 0.0238(3) Uani d . 1 . .
H H8 0.7701 0.9158 0.3005 0.029 Uiso calc R 1 . .
C C9 0.8142(2) 0.99372(12) 0.06171(12) 0.0268(4) Uani d . 1 . .
H H9 0.8099 0.9859 -0.0176 0.032 Uiso calc R 1 . .
C C10 0.8650(2) 1.08847(13) 0.12684(12) 0.0266(4) Uani d . 1 . .
H H10 0.9039 1.1597 0.1021 0.032 Uiso calc R 1 . .
H H1N 0.175(3) 0.6098(17) 0.0598(16) 0.048(5) Uiso d . 1 . .
H H2N 0.323(3) 0.7036(15) 0.0534(16) 0.044(5) Uiso d . 1 . .
H H3N 0.729(3) 0.8341(16) 0.1097(16) 0.045(5) Uiso d . 1 . .
H H4N 0.860(3) 1.1143(18) 0.2961(19) 0.060(6) Uiso d . 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C5 N1 H1N . . 114.3(12) ?
C5 N1 H2N . . 113.1(12) ?
H1N N1 H2N . . 115.1(18) ?
C8 N2 C9 . . 108.10(12) ?
C8 N2 H3N . . 125.2(12) ?
C9 N2 H3N . . 126.6(12) ?
C8 N3 C10 . . 108.23(12) ?
C8 N3 H4N . . 125.5(13) ?
C10 N3 H4N . . 125.7(13) ?
O2 C1 O1 . . 123.37(12) ?
O2 C1 C2 . . 119.86(12) ?
O1 C1 C2 . . 116.77(12) ?
C3 C2 C7 . . 118.20(12) ?
C3 C2 C1 . . 119.96(12) ?
C7 C2 C1 . . 121.83(12) ?
C4 C3 C2 . . 121.20(13) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 120.68(13) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
N1 C5 C6 . . 121.89(13) ?
N1 C5 C4 . . 119.88(13) ?
C6 C5 C4 . . 118.19(12) ?
C7 C6 C5 . . 120.69(12) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C2 . . 121.02(13) ?
C6 C7 H7 . . 119.5 ?
C2 C7 H7 . . 119.5 ?
N3 C8 N2 . . 109.39(13) ?
N3 C8 H8 . . 125.3 ?
N2 C8 H8 . . 125.3 ?
C10 C9 N2 . . 107.24(13) ?
C10 C9 H9 . . 126.4 ?
N2 C9 H9 . . 126.4 ?
C9 C10 N3 . . 107.04(13) ?
C9 C10 H10 . . 126.5 ?
N3 C10 H10 . . 126.5 ?
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
O1 C1 . 1.2987(16) ?
O2 C1 . 1.2368(16) ?
N1 C5 . 1.3858(17) ?
N1 H1N . 0.94(2) ?
N1 H2N . 0.89(2) ?
N2 C8 . 1.3281(17) ?
N2 C9 . 1.3745(19) ?
N2 H3N . 0.956(19) ?
N3 C8 . 1.3200(19) ?
N3 C10 . 1.3794(18) ?
N3 H4N . 0.93(2) ?
C1 C2 . 1.4996(18) ?
C2 C3 . 1.3900(19) ?
C2 C7 . 1.3964(18) ?
C3 C4 . 1.3825(18) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.4016(19) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.397(2) ?
C6 C7 . 1.3850(18) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C10 . 1.349(2) ?
C9 H9 . 0.9500 ?
C10 H10 . 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
N3 H4N O1 3_676 0.93(2) 1.76(2) 2.6869(15) 171(2)
N2 H3N O1 4_675 0.956(19) 1.742(19) 2.6938(15) 173.5(19)
N1 H1N O2 2_545 0.94(2) 2.17(2) 2.9495(16) 139.3(17)
N1 H2N O1 4_675 0.89(2) 2.20(2) 3.0149(17) 152.0(16)
C6 H6 O2 4_575 0.95 2.55 3.3533(16) 142
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C2 C3 . . . . 12.6(2) ?
O1 C1 C2 C3 . . . . -167.05(12) ?
O2 C1 C2 C7 . . . . -166.47(12) ?
O1 C1 C2 C7 . . . . 13.89(18) ?
C7 C2 C3 C4 . . . . -0.2(2) ?
C1 C2 C3 C4 . . . . -179.26(12) ?
C2 C3 C4 C5 . . . . -0.5(2) ?
C3 C4 C5 N1 . . . . 178.96(13) ?
C3 C4 C5 C6 . . . . 1.1(2) ?
N1 C5 C6 C7 . . . . -178.90(13) ?
C4 C5 C6 C7 . . . . -1.1(2) ?
C5 C6 C7 C2 . . . . 0.5(2) ?
C3 C2 C7 C6 . . . . 0.2(2) ?
C1 C2 C7 C6 . . . . 179.26(12) ?
C10 N3 C8 N2 . . . . 0.15(16) ?
C9 N2 C8 N3 . . . . -0.43(16) ?
C8 N2 C9 C10 . . . . 0.55(17) ?
N2 C9 C10 N3 . . . . -0.45(17) ?
C8 N3 C10 C9 . . . . 0.19(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655941
