#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/83/2238358.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_2238358
loop_
_publ_author_name
'Vumbaco, David J.'
'Kammer, Michael N.'
'Koplitz, Lynn V.'
'Mague, Joel T.'
_publ_section_title
;
 2-Cyanoanilinium iodide
;
_journal_coeditor_code           HB7106
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1288
_journal_paper_doi               10.1107/S1600536813019314
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C7 H7 N2 +, I -'
_chemical_formula_moiety         'C7 H7 N2 +, I -'
_chemical_formula_sum            'C7 H7 I N2'
_chemical_formula_weight         246.05
_chemical_name_systematic
;
2-Cyanoanilinium iodide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1474(15)
_cell_length_b                   8.6979(13)
_cell_length_c                   18.073(3)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.090
_cell_measurement_theta_min      2.254
_cell_volume                     1595.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0390
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25911
_diffrn_reflns_theta_full        28.850
_diffrn_reflns_theta_max         29.090
_diffrn_reflns_theta_min         2.254
_exptl_absorpt_coefficient_mu    3.939
_exptl_absorpt_correction_T_max  0.58
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Bruker, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.583
_refine_ls_extinction_coef       0.00151(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL2013 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0162
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0208P)²+0.7585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0408
_reflns_number_gt                2030
_reflns_number_total             2112
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7106.cif
_cod_data_source_block           I
_cod_original_cell_volume        1595.2(4)
_cod_database_code               2238358
_cod_database_fobs_code          2238358
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.514
_shelx_estimated_absorpt_t_max   0.577
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_occupancy
I I1 0.58823(2) 0.05477(2) 0.13679(2) 0.01326(5) Uani d 1
N N1 0.58054(12) 0.44877(14) 0.19889(8) 0.0140(3) Uani d 1
H H1A 0.5870 0.3496 0.1900 0.017 Uiso d 1
H H1B 0.5590 0.4716 0.2448 0.017 Uiso d 1
H H1C 0.6593 0.4909 0.1973 0.017 Uiso d 1
N N2 0.28338(14) 0.23930(17) 0.21818(8) 0.0246(3) Uani d 1
C C1 0.49549(15) 0.51204(18) 0.14089(7) 0.0129(3) Uani d 1
C C2 0.54089(14) 0.63213(16) 0.09804(8) 0.0149(3) Uani d 1
H H2 0.6252 0.6758 0.1071 0.018 Uiso calc 1
C C3 0.46120(15) 0.68861(17) 0.04120(8) 0.0170(3) Uani d 1
H H3 0.4916 0.7711 0.0113 0.020 Uiso calc 1
C C4 0.33787(15) 0.62516(17) 0.02809(8) 0.0183(3) Uani d 1
H H4 0.2854 0.6627 -0.0115 0.022 Uiso calc 1
C C5 0.29073(15) 0.50692(19) 0.07257(8) 0.0172(3) Uani d 1
H H5 0.2054 0.4654 0.0643 0.021 Uiso calc 1
C C6 0.36974(17) 0.44965(16) 0.12950(8) 0.0141(3) Uani d 1
C C7 0.32073(14) 0.33165(17) 0.17807(8) 0.0167(3) Uani 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 106.4
C1 N1 H1B 116.3
H1A N1 H1B 114.3
C1 N1 H1C 110.8
H1A N1 H1C 109.6
H1B N1 H1C 99.3
C2 C1 C6 120.98(13)
C2 C1 N1 119.30(13)
C6 C1 N1 119.72(13)
C1 C2 C3 119.07(14)
C1 C2 H2 120.5
C3 C2 H2 120.5
C4 C3 C2 120.51(14)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.37(14)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 119.51(14)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C6 C1 119.52(14)
C5 C6 C7 120.37(15)
C1 C6 C7 120.07(14)
N2 C7 C6 178.30(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.4651(19)
N1 H1A 0.8800
N1 H1B 0.8800
N1 H1C 0.8800
N2 C7 1.146(2)
C1 C2 1.380(2)
C1 C6 1.402(2)
C2 C3 1.397(2)
C2 H2 0.9500
C3 C4 1.388(2)
C3 H3 0.9500
C4 C5 1.390(2)
C4 H4 0.9500
C5 C6 1.396(2)
C5 H5 0.9500
C6 C7 1.439(2)
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 I1 . 0.88 2.74 3.6069(13) 169
N1 H1B I1 3_655 0.88 2.71 3.5501(14) 160
N1 H1C I1 8_765 0.88 2.84 3.6615(13) 156
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 -1.9(2)
N1 C1 C2 C3 177.87(13)
C1 C2 C3 C4 0.2(2)
C2 C3 C4 C5 1.6(2)
C3 C4 C5 C6 -1.6(2)
C4 C5 C6 C1 -0.1(2)
C4 C5 C6 C7 177.45(14)
C2 C1 C6 C5 1.9(2)
N1 C1 C6 C5 -177.89(13)
C2 C1 C6 C7 -175.70(13)
N1 C1 C6 C7 4.5(2)
