#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/29/2232997.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_2232997
loop_
_publ_author_name
'Han, Li-Jun'
'Yang, Shu-Ping'
'Tao, Xin'
'Ma, Yuan-Feng'
_publ_section_title
;
 4-Carboxyanilinium chloride
;
_journal_coeditor_code           WN2458
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3247
_journal_paper_doi               10.1107/S1600536811046721
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H8 N O2 +, Cl -'
_chemical_formula_moiety         'C7 H8 N O2 +, Cl -'
_chemical_formula_sum            'C7 H8 Cl N O2'
_chemical_formula_weight         173.59
_chemical_name_systematic
;
4-Carboxyanilinium chloride
;
_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                 96.371(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.601(5)
_cell_length_b                   8.269(5)
_cell_length_c                   17.118(5)
_cell_measurement_reflns_used    3678
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.34
_cell_measurement_theta_min      2.39
_cell_volume                     787.9(9)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Berndt, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4205
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.8817
_exptl_absorpt_correction_T_min  0.8135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.343
_refine_ls_extinction_coef       0.075(12)
_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   1.255
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0544
_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)+(0.0616P)²+2.6608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1898
_refine_ls_wR_factor_ref         0.1921
_reflns_number_gt                1210
_reflns_number_total             1299
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wn2458.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232997
_cod_database_fobs_code          2232997
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_occupancy
_atom_site_symmetry_multiplicity
C C1 0.5758(9) 0.2824(5) 0.5157(3) 0.0322(11) Uani d 1 1
C C2 0.3637(8) 0.1926(6) 0.4999(3) 0.0332(11) Uani d 1 1
C C3 0.3059(9) 0.1230(6) 0.4273(3) 0.0367(12) Uani d 1 1
C C4 0.4607(8) 0.1434(5) 0.3701(3) 0.0314(11) Uani d 1 1
C C5 0.6671(9) 0.2347(6) 0.3835(3) 0.0362(12) Uani d 1 1
C C6 0.7245(9) 0.3053(6) 0.4564(3) 0.0376(12) Uani d 1 1
C C7 0.6379(9) 0.3487(6) 0.5964(3) 0.0348(11) Uani d 1 1
N N1 0.4043(9) 0.0640(6) 0.2933(3) 0.0374(10) Uani d 1 1
O O1 0.8194(7) 0.4512(5) 0.6027(2) 0.0488(11) Uani d 1 1
O O2 0.5313(8) 0.3078(5) 0.6508(2) 0.0573(12) Uani d 1 1
Cl Cl1 0.9009(2) 0.60977(15) 0.76491(7) 0.0407(5) Uani d 1 1
H H1 0.858(13) 0.482(9) 0.659(5) 0.09(2) Uiso d 1 1
H H1A 0.279(10) 0.006(6) 0.293(3) 0.032(14) Uiso d 1 1
H H1B 0.393(14) 0.131(11) 0.253(5) 0.09(3) Uiso d 1 1
H H1C 0.545(14) 0.002(9) 0.286(4) 0.08(2) Uiso d 1 1
H H2 0.262(9) 0.183(6) 0.541(3) 0.034(13) Uiso d 1 1
H H3 0.175(10) 0.067(6) 0.419(3) 0.033(13) Uiso d 1 1
H H5 0.780(10) 0.249(6) 0.347(3) 0.042(15) Uiso d 1 1
H H6 0.863(9) 0.363(6) 0.465(3) 0.026(12) 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'
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
C6 C1 C2 119.6(5)
C6 C1 C7 121.8(5)
C2 C1 C7 118.6(4)
C3 C2 C1 120.4(4)
C3 C2 H2 122(3)
C1 C2 H2 117(3)
C2 C3 C4 119.0(5)
C2 C3 H3 118(3)
C4 C3 H3 123(3)
C5 C4 C3 121.7(5)
C5 C4 N1 119.1(4)
C3 C4 N1 119.1(4)
C4 C5 C6 119.3(4)
C4 C5 H5 125(3)
C6 C5 H5 116(3)
C5 C6 C1 120.1(5)
C5 C6 H6 118(3)
C1 C6 H6 121(3)
O2 C7 O1 124.0(5)
O2 C7 C1 121.8(5)
O1 C7 C1 114.2(4)
C4 N1 H1A 111(3)
C4 N1 H1B 114(5)
H1A N1 H1B 111(6)
C4 N1 H1C 104(5)
H1A N1 H1C 113(6)
H1B N1 H1C 103(6)
C7 O1 H1 109(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.395(6)
C1 C2 1.402(7)
C1 C7 1.491(7)
C2 C3 1.374(7)
C2 H2 0.96(5)
C3 C4 1.389(6)
C3 H3 0.87(6)
C4 C5 1.378(7)
C4 N1 1.471(7)
C5 C6 1.383(7)
C5 H5 0.94(5)
C6 H6 0.91(5)
C7 O2 1.209(6)
C7 O1 1.319(6)
N1 H1A 0.85(6)
N1 H1B 0.88(9)
N1 H1C 0.96(8)
O1 H1 0.99(8)
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
O1 H1 Cl1 . 0.99(8) 2.10(8) 3.059(4) 164(6)
N1 H1A Cl1 4_465 0.85(6) 2.33(6) 3.154(6) 165(5)
N1 H1B O2 4_565 0.88(9) 2.05(8) 2.823(6) 145(7)
N1 H1B Cl1 3_666 0.88(9) 2.70(9) 3.289(5) 125(6)
N1 H1C Cl1 4_565 0.96(8) 2.26(8) 3.215(5) 172(6)
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 2.1(7)
C7 C1 C2 C3 -176.9(4)
C1 C2 C3 C4 -0.1(7)
C2 C3 C4 C5 -1.6(7)
C2 C3 C4 N1 177.7(4)
C3 C4 C5 C6 1.4(7)
N1 C4 C5 C6 -177.9(5)
C4 C5 C6 C1 0.7(8)
C2 C1 C6 C5 -2.3(7)
C7 C1 C6 C5 176.6(5)
C6 C1 C7 O2 -167.9(5)
C2 C1 C7 O2 11.1(7)
C6 C1 C7 O1 10.8(7)
C2 C1 C7 O1 -170.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21626863
