#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/65/2016546.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_2016546
loop_
_publ_author_name
'Cinčić, Dominik'
'Kaitner, Branko'
_publ_section_title
;
 Hydrogen bonding in the bromide salts of 4-aminobenzoic acid and
 4-aminoacetophenone
;
_journal_coeditor_code           GD3202
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o226
_journal_page_last               o229
_journal_paper_doi               10.1107/S0108270108006471
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H8 N O2 + , Br -'
_chemical_formula_moiety         'C7 H8 N O2 + , Br -'
_chemical_formula_sum            'C7 H8 Br N O2'
_chemical_formula_weight         218.05
_chemical_name_systematic
;
4-carboxyanilinium bromide
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.660(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8209(9)
_cell_length_b                   8.5101(11)
_cell_length_c                   16.648(3)
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    295
_cell_measurement_theta_max      35
_cell_measurement_theta_min      4
_cell_volume                     819.1(2)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995), Mercury
(Version 1.4; Macrae et al.,  2006) and POV-RAY (Persistence of
Vision Team, 2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7029
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    4.966
_exptl_absorpt_correction_T_max  0.61894
_exptl_absorpt_correction_T_min  0.29406
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Alcock, 1970)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.597
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0302
_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)+(0.0516P)²+0.4207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                1573
_reflns_number_total             1787
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3202.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016546
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
Br Br1 0.91216(5) 0.36393(3) 0.273722(18) 0.04142(14) Uani d . 1
O O1 0.8162(4) 0.9638(3) 0.59961(14) 0.0487(5) Uani d . 1
O O2 0.5421(5) 0.8338(4) 0.65491(16) 0.0637(7) Uani d . 1
N N1 0.4156(5) 0.5442(4) 0.29843(18) 0.0408(6) Uani d . 1
C C1 0.5832(5) 0.7887(3) 0.51721(17) 0.0329(6) Uani d . 1
C C2 0.7277(5) 0.7977(4) 0.45628(19) 0.0396(6) Uani d . 1
H H2 0.8626 0.8571 0.4641 0.048 Uiso calc R 1
C C3 0.6705(5) 0.7182(4) 0.38407(17) 0.0381(6) Uani d . 1
H H3 0.7672 0.7229 0.3434 0.046 Uiso calc R 1
C C4 0.4690(5) 0.6323(3) 0.37328(17) 0.0310(6) Uani d . 1
C C5 0.3199(5) 0.6246(3) 0.43172(18) 0.0353(6) Uani d . 1
H H5 0.1825 0.5683 0.4226 0.042 Uiso calc R 1
C C6 0.3786(5) 0.7027(4) 0.50459(18) 0.0360(6) Uani d . 1
H H6 0.2810 0.6975 0.5450 0.043 Uiso calc R 1
C C7 0.6431(5) 0.8644(3) 0.59718(19) 0.0380(7) Uani d . 1
H H1 0.8573 1.0030 0.6412 0.069(14) Uiso d . 1
H H1A 0.516(8) 0.482(6) 0.288(3) 0.071(14) Uiso d . 1
H H1B 0.427(7) 0.599(5) 0.258(3) 0.061(13) Uiso d . 1
H H1C 0.295(7) 0.495(5) 0.296(2) 0.056(11) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0356(2) 0.0423(2) 0.0462(2) -0.00311(11) 0.00399(13) 0.00186(12)
O1 0.0578(13) 0.0521(13) 0.0356(12) -0.0177(11) 0.0035(10) -0.0018(10)
O2 0.0573(15) 0.0934(19) 0.0434(14) -0.0268(14) 0.0186(12) -0.0170(13)
N1 0.0372(14) 0.0485(16) 0.0381(14) -0.0037(13) 0.0098(11) -0.0014(12)
C1 0.0339(13) 0.0331(13) 0.0323(14) 0.0031(11) 0.0069(10) 0.0039(11)
C2 0.0322(14) 0.0409(16) 0.0464(17) -0.0068(12) 0.0077(12) 0.0008(13)
C3 0.0376(14) 0.0494(17) 0.0296(14) -0.0055(12) 0.0137(11) 0.0021(12)
C4 0.0327(13) 0.0347(14) 0.0257(13) 0.0022(10) 0.0042(10) 0.0038(10)
C5 0.0276(13) 0.0403(15) 0.0387(16) -0.0030(10) 0.0073(11) 0.0052(11)
C6 0.0318(13) 0.0427(15) 0.0344(14) 0.0007(11) 0.0083(10) 0.0030(12)
C7 0.0356(15) 0.0416(16) 0.0369(16) 0.0012(11) 0.0041(12) 0.0005(12)
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'
Br Br -0.2901 2.4595 '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 O1 H1 117.2
C4 N1 H1A 115(3)
C4 N1 H1B 112(3)
H1A N1 H1B 94(4)
C4 N1 H1C 113(3)
H1A N1 H1C 107(4)
H1B N1 H1C 114(4)
C2 C1 C6 119.8(3)
C2 C1 C7 122.1(3)
C6 C1 C7 118.1(3)
C3 C2 C1 120.0(3)
C3 C2 H2 120.0
C1 C2 H2 120.0
C4 C3 C2 119.2(3)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 122.0(3)
C3 C4 N1 118.6(3)
C5 C4 N1 119.3(3)
C4 C5 C6 118.8(3)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C6 C1 120.1(3)
C5 C6 H6 119.9
C1 C6 H6 119.9
O2 C7 O1 123.8(3)
O2 C7 C1 122.2(3)
O1 C7 C1 114.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.312(4)
O1 H1 0.781
O2 C7 1.212(4)
N1 C4 1.456(4)
N1 H1A 0.82(5)
N1 H1B 0.83(5)
N1 H1C 0.81(4)
C1 C2 1.393(4)
C1 C6 1.393(4)
C1 C7 1.484(4)
C2 C3 1.386(4)
C2 H2 0.9300
C3 C4 1.376(4)
C3 H3 0.9300
C4 C5 1.378(4)
C5 C6 1.390(4)
C5 H5 0.9300
C6 H6 0.9300
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
N1 H1A Br1 . 0.84(6) 2.55(5) 3.343(3) 159(5) yes
O1 H1 Br1 4_576 0.78 2.47 3.238(2) 170 yes
N1 H1B O2 4_575 0.83(5) 1.99(5) 2.781(4) 158(5) yes
N1 H1C Br1 1_455 0.81(4) 2.48(4) 3.291(3) 173(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654097
