#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/64/2236406.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_2236406
loop_
_publ_author_name
'Vumbaco, David J.'
'Kammer, Michael N.'
'Koplitz, Lynn V.'
'Mague, Joel T.'
_publ_section_title
;
 4-Cyanoanilinium bromide
;
_journal_coeditor_code           JJ2147
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2884
_journal_paper_doi               10.1107/S1600536812037014
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H7 N2 +, Br -'
_chemical_formula_moiety         'C7 H7 N2 +, Br -'
_chemical_formula_sum            'C7 H7 Br N2'
_chemical_formula_weight         199.06
_chemical_name_systematic
;
4-Cyanoanilinium bromide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.719(3)
_cell_angle_beta                 93.290(3)
_cell_angle_gamma                101.428(3)
_cell_formula_units_Z            2
_cell_length_a                   4.3102(10)
_cell_length_b                   6.1076(13)
_cell_length_c                   14.510(3)
_cell_measurement_reflns_used    5589
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.81
_cell_volume                     373.45(14)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXM (Sheldrick, 1998, 2004)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6534
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    5.422
_exptl_absorpt_correction_T_max  0.8371
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0248P)²+0.1891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0510
_reflns_number_gt                1802
_reflns_number_total             1874
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jj2147.cif
_cod_data_source_block           I
_cod_original_cell_volume        373.46(14)
_cod_database_code               2236406
_cod_database_fobs_code          2236406
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Br Br1 0.08172(3) 0.73901(2) 0.423553(10) 0.01208(7) Uani d . 1 1
N N1 0.5934(3) 0.7244(2) 0.60221(10) 0.0128(3) Uani d . 1 1
H H1A 0.4298 0.7029 0.5615 0.015 Uiso d R 1 1
H H1B 0.6868 0.6102 0.5940 0.015 Uiso d R 1 1
H H1C 0.7187 0.8527 0.5922 0.015 Uiso d R 1 1
N N2 0.1311(4) 0.7765(3) 1.04130(11) 0.0215(3) Uani d . 1 1
C C1 0.4868(4) 0.7327(3) 0.69615(11) 0.0117(3) Uani d . 1 1
C C2 0.3482(4) 0.9098(3) 0.72253(12) 0.0142(3) Uani d . 1 1
H H2 0.3199 1.0208 0.6801 0.017 Uiso calc R 1 1
C C3 0.2514(4) 0.9219(3) 0.81193(12) 0.0148(3) Uani d . 1 1
H H3 0.1545 1.0409 0.8312 0.018 Uiso calc R 1 1
C C4 0.2980(4) 0.7575(3) 0.87320(12) 0.0140(3) Uani d . 1 1
C C5 0.4367(4) 0.5796(3) 0.84545(12) 0.0158(3) Uani d . 1 1
H H5 0.4650 0.4679 0.8875 0.019 Uiso calc R 1 1
C C6 0.5326(4) 0.5674(3) 0.75594(12) 0.0142(3) Uani d . 1 1
H H6 0.6278 0.4481 0.7361 0.017 Uiso calc R 1 1
C C7 0.2031(4) 0.7694(3) 0.96694(13) 0.0168(3) Uani 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'
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
C1 N1 H1A 110.3
C1 N1 H1B 110.7
H1A N1 H1B 106.0
C1 N1 H1C 108.9
H1A N1 H1C 108.7
H1B N1 H1C 112.2
C6 C1 C2 122.32(16)
C6 C1 N1 119.28(15)
C2 C1 N1 118.38(15)
C1 C2 C3 118.97(16)
C1 C2 H2 120.5
C3 C2 H2 120.5
C2 C3 C4 119.38(16)
C2 C3 H3 120.3
C4 C3 H3 120.3
C3 C4 C5 120.97(16)
C3 C4 C7 120.11(16)
C5 C4 C7 118.91(16)
C6 C5 C4 119.56(16)
C6 C5 H5 120.2
C4 C5 H5 120.2
C1 C6 C5 118.79(16)
C1 C6 H6 120.6
C5 C6 H6 120.6
N2 C7 C4 178.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.466(2)
N1 H1A 0.8800
N1 H1B 0.8801
N1 H1C 0.8800
N2 C7 1.142(3)
C1 C6 1.387(2)
C1 C2 1.389(2)
C2 C3 1.390(2)
C2 H2 0.9500
C3 C4 1.397(2)
C3 H3 0.9500
C4 C5 1.399(2)
C4 C7 1.447(2)
C5 C6 1.390(2)
C5 H5 0.9500
C6 H6 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
N1 H1A Br1 . 0.88 2.47 3.3209(16) 162
C2 H2 Br1 2_576 0.95 2.87 3.7316(18) 151
C3 H3 N2 2_577 0.95 2.62 3.466(2) 149
C5 H5 N2 2_667 0.95 2.69 3.517(2) 146
C6 H6 Br1 2_666 0.95 3.00 3.8063(18) 144
N1 H1B Br1 2_666 0.88 2.54 3.4174(16) 175
N1 H1C Br1 2_676 0.88 2.49 3.3400(16) 162
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 -0.1(3)
N1 C1 C2 C3 -178.82(15)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 C5 -0.8(3)
C2 C3 C4 C7 179.08(16)
C3 C4 C5 C6 0.7(3)
C7 C4 C5 C6 -179.23(17)
C2 C1 C6 C5 -0.1(3)
N1 C1 C6 C5 178.66(15)
C4 C5 C6 C1 -0.2(3)
C3 C4 C7 N2 -162(11)
C5 C4 C7 N2 18(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658108
