##############################################################################
#                                                                            #
# 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 # 
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data_global
_audit_creation_method     'APEX2 v2014.11-0'
_journal_date_recd_electronic     2015-10-10
_journal_date_accepted     2015-10-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue     11
_journal_page_first     o854
_journal_page_last     o855
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015019167
_journal_coeditor_code     HB7523
_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
;
Crystal structure of 2-cyano-1-methylpyridinium bromide
;
loop_
    _publ_author_name
    _publ_author_address
    'Nguyen, Vu D.'
;
Department of Chemistry
Loyola University
New Orleans, LA 70118
USA
;
    'McCormick, Cameron A.'
;
Department of Chemistry
Loyola University
New Orleans, LA 70118
USA
;
    'Pascal Jr, Robert A. '
;
Department of Chemistry
Tulane University
New Orleans, LA 70118
USA
;
    'Mague, Joel T.'
;
Department of Chemistry
Tulane University
New Orleans, LA 70118
USA
;
    'Koplitz, Lynn V.'
;
Department of Chemistry
Loyola University
New Orleans, LA 70118
USA
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1430625'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2-Cyano-1-methylpyridinium bromide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H7 N2 +, Br -'
_chemical_formula_sum     'C7 H7 Br N2'
_chemical_formula_iupac     'C7 H7 N2 +, Br -'
_chemical_formula_weight     199.06
_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     monoclinic
_space_group_name_H-M_alt     'C 2/m'
_space_group_name_Hall     '-C 2y'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
    '-x, -y, -z'
    'x, -y, z'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z'
_cell_length_a     13.3039(12)
_cell_length_b     6.5892(6)
_cell_length_c     9.3753(8)
_cell_angle_alpha     90
_cell_angle_beta     92.4190(10)
_cell_angle_gamma     90
_cell_volume     821.13(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9936
_cell_measurement_theta_min     2.1742
_cell_measurement_theta_max     29.1180
_cell_measurement_temperature     150.(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.197
_exptl_crystal_size_mid     0.149
_exptl_crystal_size_min     0.064
_exptl_crystal_density_diffrn     1.610
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     392
_exptl_absorpt_coefficient_mu     4.932
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Sheldrick, 2009)
;
_shelx_estimated_absorpt_T_min     0.443
_shelx_estimated_absorpt_T_max     0.743
_exptl_absorpt_correction_T_min     0.44
_exptl_absorpt_correction_T_max     0.74
_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 20 sec/frame. Analysis of 1897 reflections having I/σ(I) > 13
and chosen from the full data set with CELL_NOW (Sheldrick, 2008a)
showed the crystal to belong to the monoclinic system and to be twinned by a
180 ° rotation about a*. The raw data were processed using the
multi-component version of SAINT under control of the two-component
orientation file generated by CELL_NOW.
;
_diffrn_ambient_temperature     150(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     22367
_diffrn_reflns_av_R_equivalents     0.0210
_diffrn_reflns_theta_min     2.174
_diffrn_reflns_theta_max     29.118
_diffrn_reflns_theta_full     28.500
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. H-atoms attached to carbon were placed in calculated positions
(C---H = 0.95 - 0.98 Å). All were included as riding contributions with
isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.
Trial refinements with the single-component reflection file extracted from the
full dataset with TWINABS and with the full, 2-component reflection
file indicated the former refinement to be superior.
;
_reflns_number_total     1179
_reflns_number_gt     1084
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0258
_refine_ls_R_factor_gt     0.0225
_refine_ls_wR_factor_gt     0.0473
_refine_ls_wR_factor_ref     0.0481
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     1179
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0234P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.514
_refine_diff_density_min     -0.438
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014) and CELL_NOW (Sheldrick,
2008a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008b)
;
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
    N N1 0.29873(14) 0.0000 0.32868(18) 0.0177(4) Uani d 1 . .
    N N2 0.53530(17) 0.0000 0.1900(3) 0.0399(6) Uani d 1 . .
    C C1 0.36322(18) 0.0000 0.4616(2) 0.0239(5) Uani d 1 . .
    H H1A 0.3212 0.0177 0.5440 0.036 Uiso calc 0.5 . .
    H H1B 0.4118 0.1116 0.4584 0.036 Uiso calc 0.5 . .
    H H1C 0.3993 -0.1293 0.4701 0.036 Uiso calc 0.5 . .
    C C2 0.19853(17) 0.0000 0.3369(2) 0.0218(5) Uani d 1 . .
    H H2 0.1698 0.0000 0.4280 0.026 Uiso calc 1 . .
    C C3 0.13619(18) 0.0000 0.2157(2) 0.0269(5) Uani d 1 . .
    H H3 0.0652 0.0000 0.2229 0.032 Uiso calc 1 . .
    C C4 0.17863(19) 0.0000 0.0830(3) 0.0273(5) Uani d 1 . .
    H H4 0.1368 0.0000 -0.0017 0.033 Uiso calc 1 . .
    C C5 0.28191(18) 0.0000 0.0749(2) 0.0237(5) Uani d 1 . .
    H H5 0.3120 0.0000 -0.0152 0.028 Uiso calc 1 . .
    C C6 0.34090(17) 0.0000 0.1994(2) 0.0198(4) Uani d 1 . .
    C C7 0.44985(19) 0.0000 0.1969(3) 0.0280(5) Uani d 1 . .
    Br Br1 0.36532(2) 0.5000 0.29528(2) 0.02252(9) Uani d 1 . .
_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 C2 . 1.339(3) ?
    N1 C6 . 1.357(3) ?
    N1 C1 . 1.482(3) ?
    N2 C7 . 1.141(3) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 C3 . 1.378(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.388(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.379(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.379(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.451(3) ?
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
    C2 N1 C6 . . 120.12(19) ?
    C2 N1 C1 . . 119.61(18) ?
    C6 N1 C1 . . 120.28(18) ?
    N1 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 C3 . . 121.25(19) ?
    N1 C2 H2 . . 119.4 ?
    C3 C2 H2 . . 119.4 ?
    C2 C3 C4 . . 119.1(2) ?
    C2 C3 H3 . . 120.5 ?
    C4 C3 H3 . . 120.5 ?
    C5 C4 C3 . . 119.5(2) ?
    C5 C4 H4 . . 120.2 ?
    C3 C4 H4 . . 120.2 ?
    C6 C5 C4 . . 119.1(2) ?
    C6 C5 H5 . . 120.4 ?
    C4 C5 H5 . . 120.4 ?
    N1 C6 C5 . . 120.9(2) ?
    N1 C6 C7 . . 117.8(2) ?
    C5 C6 C7 . . 121.3(2) ?
    N2 C7 C6 . . 177.7(3) ?
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 N1 C2 C3 . . . . 0.000000 ?
    C1 N1 C2 C3 . . . . 180.000000 ?
    N1 C2 C3 C4 . . . . 0.000000 ?
    C2 C3 C4 C5 . . . . 0.000000 ?
    C3 C4 C5 C6 . . . . 0.000000 ?
    C2 N1 C6 C5 . . . . 0.000000 ?
    C1 N1 C6 C5 . . . . 180.000000 ?
    C2 N1 C6 C7 . . . . 180.000000 ?
    C1 N1 C6 C7 . . . . 0.000000 ?
    C4 C5 C6 N1 . . . . 0.000000 ?
    C4 C5 C6 C7 . . . . 180.0 ?
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
    C5 H5 N2 5_655 0.95 2.66 3.549(3) 155
    C1 H1A Br1 7_556 0.98 2.96 3.876(2) 156
    C2 H2 Br1 7_556 0.95 2.66 3.586(2) 166
    C3 H3 Br1 3_445 0.95 2.77 3.711(2) 170
