##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_global
_audit_creation_method     'APEX2 v2013.6-2'
_journal_date_recd_electronic     2013-07-11
_journal_date_accepted     2013-07-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      8
_journal_page_first     o1288
_journal_page_last     o1288
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813019314
_journal_coeditor_code     HB7106
_publ_contact_author_name     'Joel T. Mague'
_publ_contact_author_address
;
Department of Chemistry
Tulane University
New Orleans, LA 70118
USA
;
_publ_contact_author_email     joelt@tulane.edu
_publ_contact_author_fax     504-865-5596
_publ_contact_author_phone     504-862-3585
_publ_section_title
;
2-Cyanoanilinium iodide
;
loop_
    _publ_author_name
    _publ_author_address
    'Vumbaco, David J.'
;
Department of Biological Sciences
      Loyola University
      New Orleans, LA 70118
      USA
;
    'Kammer, Michael N.'
;
Department of Physics
      Loyola University
      New Orleans, LA 70118
      USA
;
    'Koplitz, Lynn V.'
;
Department of Chemistry
      Loyola University
      New Orleans, LA 70118
      USA
;
    'Mague, Joel T.'
;
Department of Chemistry
      Tulane University
      New Orleans, LA 70118
      USA
;
data_I
_audit_creation_method     SHELXL-2013
_chemical_name_systematic
;
2-Cyanoanilinium iodide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H7 N2 +, I -'
_chemical_formula_sum     'C7 H7 I N2'
_chemical_formula_iupac     'C7 H7 N2 +, I -'
_chemical_formula_weight     246.05
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
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'
_cell_length_a     10.1474(15)
_cell_length_b     8.6979(13)
_cell_length_c     18.073(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1595.2(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9853
_cell_measurement_theta_min     2.254
_cell_measurement_theta_max     29.090
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.195
_exptl_crystal_size_mid     0.191
_exptl_crystal_size_min     0.157
_exptl_crystal_density_diffrn     2.049
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     928
_exptl_absorpt_coefficient_mu     3.939
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(SADABS; Bruker, 2010)'
_shelx_estimated_absorpt_T_min     0.514
_shelx_estimated_absorpt_T_max     0.577
_exptl_absorpt_correction_T_min     0.43
_exptl_absorpt_correction_T_max     0.58
_exptl_special_details
;
The diffraction data were obtained from 3 sets of 400 frames, each of width
0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800
frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The
scan time was 10 sec/frame.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3660
_diffrn_reflns_number     25911
_diffrn_reflns_av_R_equivalents     0.0390
_diffrn_reflns_theta_min     2.254
_diffrn_reflns_theta_max     29.090
_diffrn_reflns_theta_full     28.850
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_refine_special_details
;
;
_reflns_number_total     2112
_reflns_number_gt     2030
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0168
_refine_ls_R_factor_gt     0.0162
_refine_ls_wR_factor_gt     0.0402
_refine_ls_wR_factor_ref     0.0408
_refine_ls_goodness_of_fit_ref     1.100
_refine_ls_restrained_S_all     1.100
_refine_ls_number_reflns     2112
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0208P)²+0.7585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.592
_refine_diff_density_min     -0.583
_refine_ls_extinction_method     'SHELXL2013 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.00151(13)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2010)'
_computing_cell_refinement     'SAINT (Bruker, 2010)'
_computing_data_reduction     'SAINT (Bruker, 2010)'
_computing_structure_solution     'SHELXM (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL2013 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_disorder_assembly
    _atom_site_disorder_group
    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_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
    I1 0.01359(7) 0.01201(7) 0.01419(7) -0.00040(3) -0.00112(3) -0.00004(3)
    N1 0.0147(6) 0.0120(6) 0.0152(6) -0.0004(4) -0.0008(4) 0.0005(4)
    N2 0.0270(7) 0.0236(7) 0.0233(7) -0.0071(6) 0.0076(6) -0.0023(6)
    C1 0.0145(7) 0.0117(7) 0.0126(6) 0.0012(5) 0.0003(5) -0.0022(5)
    C2 0.0153(6) 0.0120(6) 0.0174(6) -0.0003(5) 0.0003(5) -0.0002(5)
    C3 0.0210(7) 0.0127(7) 0.0174(7) 0.0019(6) 0.0010(5) 0.0009(5)
    C4 0.0213(7) 0.0163(7) 0.0174(6) 0.0050(6) -0.0035(5) -0.0020(6)
    C5 0.0150(6) 0.0166(7) 0.0199(7) 0.0020(6) -0.0011(5) -0.0058(6)
    C6 0.0142(8) 0.0119(7) 0.0161(7) 0.0012(5) 0.0029(5) -0.0033(5)
    C7 0.0143(6) 0.0174(7) 0.0182(7) -0.0017(5) 0.0023(5) -0.0053(6)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    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_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
    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_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
    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) ?
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
_shelx_hkl_checksum     97707
_shelx_res_checksum     26589
_shelxl_version_number        2.013
_iucr_refine_instructions_details
;
TITL LK109_1m in Pbca
CELL 0.71073  10.1474   8.6979  18.0733  90.000  90.000  90.000
ZERR    8.00   0.0015   0.0013   0.0026   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C  H  N  I
UNIT 56  56  16  8
REM TRY      1   FINAL CC 89.90   TIME       0 SECS
REM Fragments: 4 2
REM
L.S. 4
BOND $H
FMAP 2
PLAN 5
ACTA 57.7
EQIV $1 -x+1, y+0.5, -z+0.5
EQIV $2 -x+1.5, y+0.5, z
HTAB N1 I1
HTAB N1 I1_$1
HTAB N1 I1_$2
SIZE 0.157 0.191 0.195
TEMP -173
CONF
WGHT    0.020800    0.758500
EXTI    0.001506
FVAR       0.08838
I1    4    0.588234    0.054767    0.136791    11.00000    0.01359    0.01201 =
         0.01419   -0.00004   -0.00112   -0.00040
N1    3    0.580537    0.448767    0.198886    11.00000    0.01469    0.01203 =
         0.01521    0.00048   -0.00081   -0.00039
AFIX   3
H1A   2    0.586997    0.349577    0.190006    11.00000   -1.20000
H1B   2    0.559027    0.471627    0.244756    11.00000   -1.20000
H1C   2    0.659328    0.490907    0.197296    11.00000   -1.20000
AFIX   0
N2    3    0.283378    0.239295    0.218179    11.00000    0.02698    0.02360 =
         0.02327   -0.00227    0.00756   -0.00711
C1    1    0.495492    0.512038    0.140887    11.00000    0.01450    0.01170 =
         0.01262   -0.00220    0.00031    0.00123
C2    1    0.540895    0.632129    0.098038    11.00000    0.01533    0.01201 =
         0.01741   -0.00018    0.00033   -0.00032
AFIX  43
H2    2    0.625188    0.675795    0.107064    11.00000   -1.20000
AFIX   0
C3    1    0.461196    0.688614    0.041201    11.00000    0.02102    0.01268 =
         0.01736    0.00092    0.00097    0.00190
AFIX  43
H3    2    0.491622    0.771103    0.011282    11.00000   -1.20000
AFIX   0
C4    1    0.337868    0.625155    0.028088    11.00000    0.02128    0.01632 =
         0.01741   -0.00197   -0.00351    0.00498
AFIX  43
H4    2    0.285384    0.662728   -0.011506    11.00000   -1.20000
AFIX   0
C5    1    0.290732    0.506925    0.072574    11.00000    0.01495    0.01655 =
         0.01995   -0.00577   -0.00112    0.00201
AFIX  43
H5    2    0.205400    0.465412    0.064302    11.00000   -1.20000
AFIX   0
C6    1    0.369736    0.449649    0.129500    11.00000    0.01419    0.01191 =
         0.01613   -0.00328    0.00287    0.00117
C7    1    0.320734    0.331649    0.178071    11.00000    0.01428    0.01743 =
         0.01824   -0.00527    0.00228   -0.00175
HKLF 4
REM  LK109_1m in Pbca
REM R1 =  0.0162 for    2030 Fo > 4sig(Fo)  and  0.0168 for all    2112 data
REM     92 parameters refined using      0 restraints
END
WGHT      0.0208      0.7584
REM Highest difference peak  0.592,  deepest hole -0.583,  1-sigma level  0.118
Q1    1   0.3977  0.6579  0.0358  11.00000  0.05    0.59
Q2    1   0.4976  0.6590  0.0665  11.00000  0.05    0.46
Q3    1   0.5884  0.1029  0.1721  11.00000  0.05    0.46
Q4    1   0.3427  0.2803  0.2069  11.00000  0.05    0.42
Q5    1   0.5166  0.0848  0.1383  11.00000  0.05    0.39
;
