##############################################################################
#                                                                            #
# 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.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,6-Dimethylpyridinium bromide
;
_chemical_name_common     '(2,6-DMPyH).Br'
_chemical_formula_moiety     'C7 H10 N +, Br -'
_chemical_formula_sum     'C7 H10 Br N'
_chemical_formula_iupac     'C7 H10 N +, Br -'
_chemical_formula_weight     188.06
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n m a'
_symmetry_space_group_name_Hall     '-P 2ac 2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     15.0788(13)
_cell_length_b     20.432(3)
_cell_length_c     7.8456(7)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2417.2(5)
_cell_formula_units_Z     12
_cell_measurement_reflns_used     1341
_cell_measurement_theta_min     2.9847
_cell_measurement_theta_max     29.2700
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.550
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1128
_exptl_absorpt_coefficient_mu     5.017
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2011)'
_exptl_absorpt_correction_T_min     0.242
_exptl_absorpt_correction_T_max     0.367
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Agilent Xcalibur Eos'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.0534
_diffrn_reflns_number     6863
_diffrn_reflns_av_R_equivalents     0.0363
_diffrn_reflns_av_sigmaI/netI     0.0388
_diffrn_reflns_theta_min     3.36
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     7
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0.0
_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.
;
_reflns_number_total     2194
_reflns_number_gt     1708
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0584
_refine_ls_R_factor_gt     0.0404
_refine_ls_wR_factor_gt     0.0935
_refine_ls_wR_factor_ref     0.1020
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     2194
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0499P)²+0.7328P] 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     0.456
_refine_diff_density_min     -0.430
_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     'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.0302(2) 0.08268(13) 0.5688(4) 0.0385(7) Uani d . 1 1 . .
    H H1A 0.0643 0.0802 0.6564 0.046 Uiso d R 1 1 . .
    C C1 -0.0586(3) 0.08263(16) 0.5951(5) 0.0397(9) Uani d . 1 1 . .
    C C2 -0.1132(3) 0.08487(18) 0.4561(6) 0.0477(10) Uani d . 1 1 . .
    H H2B -0.1744 0.0839 0.4697 0.057 Uiso calc R 1 1 . .
    C C3 -0.0765(3) 0.08853(18) 0.2958(6) 0.0511(11) Uani d . 1 1 . .
    H H3A -0.1134 0.0908 0.2011 0.061 Uiso calc R 1 1 . .
    C C4 0.0140(3) 0.08893(17) 0.2736(5) 0.0503(10) Uani d . 1 1 . .
    H H4A 0.0380 0.0910 0.1646 0.060 Uiso calc R 1 1 . .
    C C5 0.0685(3) 0.08625(17) 0.4130(5) 0.0419(10) Uani d . 1 1 . .
    C C6 -0.0902(3) 0.07923(18) 0.7754(5) 0.0519(11) Uani d . 1 1 . .
    H H6A -0.0420 0.0892 0.8510 0.078 Uiso calc R 1 1 . .
    H H6B -0.1117 0.0360 0.7990 0.078 Uiso calc R 1 1 . .
    H H6C -0.1372 0.1103 0.7920 0.078 Uiso calc R 1 1 . .
    C C7 0.1671(3) 0.08641(19) 0.4050(6) 0.0568(12) Uani d . 1 1 . .
    H H7A 0.1896 0.1233 0.4675 0.085 Uiso calc R 1 1 . .
    H H7B 0.1857 0.0894 0.2883 0.085 Uiso calc R 1 1 . .
    H H7C 0.1895 0.0467 0.4541 0.085 Uiso calc R 1 1 . .
    N N2 0.4525(3) 0.2500 0.7490(5) 0.0406(10) Uani d S 1 2 . .
    H H2A 0.4164 0.2500 0.6640 0.049 Uiso d SR 1 2 . .
    C C8 0.4177(4) 0.2500 0.9087(7) 0.0403(13) Uani d S 1 2 . .
    C C9 0.4755(4) 0.2500 1.0449(7) 0.0450(13) Uani d S 1 2 . .
    H H9A 0.4542 0.2500 1.1561 0.054 Uiso calc SR 1 2 . .
    C C10 0.5655(4) 0.2500 1.0135(7) 0.0480(14) Uani d S 1 2 . .
    H H10A 0.6049 0.2500 1.1047 0.058 Uiso calc SR 1 2 . .
    C C11 0.5977(4) 0.2500 0.8509(8) 0.0502(15) Uani d S 1 2 . .
    H H11A 0.6585 0.2500 0.8319 0.060 Uiso calc SR 1 2 . .
    C C12 0.5402(3) 0.2500 0.7161(7) 0.0397(12) Uani d S 1 2 . .
    C C13 0.3189(4) 0.2500 0.9253(8) 0.0522(15) Uani d S 1 2 . .
    H H13A 0.2969 0.2063 0.9096 0.078 Uiso calc PR 0.50 1 . .
    H H13B 0.2937 0.2783 0.8404 0.078 Uiso calc PR 0.50 1 . .
    H H13C 0.3026 0.2654 1.0366 0.078 Uiso calc PR 0.50 1 . .
    C C14 0.5682(4) 0.2500 0.5325(7) 0.0578(16) Uani d S 1 2 . .
    H H14A 0.5901 0.2926 0.5023 0.087 Uiso calc PR 0.50 1 . .
    H H14B 0.5182 0.2393 0.4619 0.087 Uiso calc PR 0.50 1 . .
    H H14C 0.6141 0.2181 0.5158 0.087 Uiso calc PR 0.50 1 . .
    Br Br1 0.31927(4) 0.2500 0.43172(8) 0.0566(2) Uani d S 1 2 . .
    Br Br2 0.15804(3) 0.07357(3) 0.89056(6) 0.0627(2) Uani d . 1 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 C1 . 1.354(5) ?
    N1 C5 . 1.354(5) ?
    N1 H1A . 0.8600 ?
    C1 C2 . 1.368(6) ?
    C1 C6 . 1.494(5) ?
    C2 C3 . 1.376(6) ?
    C2 H2B . 0.9300 ?
    C3 C4 . 1.376(6) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.369(6) ?
    C4 H4A . 0.9300 ?
    C5 C7 . 1.487(6) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    N2 C12 . 1.348(6) ?
    N2 C8 . 1.358(6) ?
    N2 H2A . 0.8600 ?
    C8 C9 . 1.379(7) ?
    C8 C13 . 1.496(7) ?
    C9 C10 . 1.379(8) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.365(8) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.367(7) ?
    C11 H11A . 0.9300 ?
    C12 C14 . 1.501(7) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
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 C5 . . 124.0(4) ?
    C1 N1 H1A . . 118.0 ?
    C5 N1 H1A . . 117.9 ?
    N1 C1 C2 . . 118.3(4) ?
    N1 C1 C6 . . 117.4(4) ?
    C2 C1 C6 . . 124.4(4) ?
    C1 C2 C3 . . 119.2(4) ?
    C1 C2 H2B . . 120.4 ?
    C3 C2 H2B . . 120.4 ?
    C4 C3 C2 . . 121.0(4) ?
    C4 C3 H3A . . 119.5 ?
    C2 C3 H3A . . 119.5 ?
    C5 C4 C3 . . 119.6(4) ?
    C5 C4 H4A . . 120.2 ?
    C3 C4 H4A . . 120.2 ?
    N1 C5 C4 . . 117.8(4) ?
    N1 C5 C7 . . 117.7(4) ?
    C4 C5 C7 . . 124.5(4) ?
    C1 C6 H6A . . 109.5 ?
    C1 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C1 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C5 C7 H7A . . 109.5 ?
    C5 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C5 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C12 N2 C8 . . 123.8(5) ?
    C12 N2 H2A . . 118.1 ?
    C8 N2 H2A . . 118.1 ?
    N2 C8 C9 . . 118.1(5) ?
    N2 C8 C13 . . 117.7(5) ?
    C9 C8 C13 . . 124.2(5) ?
    C10 C9 C8 . . 119.0(5) ?
    C10 C9 H9A . . 120.5 ?
    C8 C9 H9A . . 120.5 ?
    C11 C10 C9 . . 121.1(5) ?
    C11 C10 H10A . . 119.5 ?
    C9 C10 H10A . . 119.5 ?
    C10 C11 C12 . . 119.9(5) ?
    C10 C11 H11A . . 120.1 ?
    C12 C11 H11A . . 120.1 ?
    N2 C12 C11 . . 118.3(5) ?
    N2 C12 C14 . . 117.3(5) ?
    C11 C12 C14 . . 124.4(5) ?
    C8 C13 H13A . . 109.5 ?
    C8 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C8 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C12 C14 H14A . . 109.5 ?
    C12 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C12 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
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
    C5 N1 C1 C2 . . . . 1.5(5) ?
    C5 N1 C1 C6 . . . . -179.3(3) ?
    N1 C1 C2 C3 . . . . -1.4(5) ?
    C6 C1 C2 C3 . . . . 179.4(4) ?
    C1 C2 C3 C4 . . . . 1.0(6) ?
    C2 C3 C4 C5 . . . . -0.6(6) ?
    C1 N1 C5 C4 . . . . -1.1(5) ?
    C1 N1 C5 C7 . . . . 179.4(3) ?
    C3 C4 C5 N1 . . . . 0.6(5) ?
    C3 C4 C5 C7 . . . . -180.0(3) ?
    C12 N2 C8 C9 . . . . 0.000(2) ?
    C12 N2 C8 C13 . . . . 180.0000(10)
                                     ?
    N2 C8 C9 C10 . . . . 0.000(2) ?
    C13 C8 C9 C10 . . . . 180.0000(10)
                                     ?
    C8 C9 C10 C11 . . . . 0.000(2) ?
    C9 C10 C11 C12 . . . . 0.000(2) ?
    C8 N2 C12 C11 . . . . 0.0000(10)
                                   ?
    C8 N2 C12 C14 . . . . 180.0 ?
    C10 C11 C12 N2 . . . . 0.0000(10)
                                    ?
    C10 C11 C12 C14 . . . . 180.0000(10)
                                       ?
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
    N2 H2A Br1 . 0.86 2.34 3.199(5) 180.0
    N1 H1A Br2 . 0.86 2.32 3.182(4) 179.3
    C4 H4A Br2 1_554 0.93 2.83 3.722(5) 160.5
    C2 H2B Br2 6_557 0.93 2.76 3.664(5) 162.8
    C9 H9A Br1 7_566 0.93 2.97 3.842(6) 157.0
data_global
_journal_date_recd_electronic     2012-07-13
_journal_date_accepted     2012-09-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue     10
_journal_page_first     o2983
_journal_page_last     o2984
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812039578
_journal_coeditor_code     LR2077
_publ_contact_author_name     'Basem F. Ali'
_publ_contact_author_address
;
Department of Chemistry
Al al-Bayt University
Mafraq 25113
Jordan
;
_publ_contact_author_email     'bfali@aabu.edu.jo'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
2,6-Dimethylpyridinium bromide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Haddad, Salim F.' .
;
Department of Chemistry
The  University of Jordan
Amman 11942
Jordan
;
    'Ali, Basem F.' .
;
Department of Chemistry
Al al-Bayt University
Mafraq 25113
Jordan
;
    'Al-Far, Rawhi' .
;
Faculty of Science and IT, Al-Balqa'a Applied University, Salt, Jordan
Qassim University, Faculty of Science, Chemistry Department,
Qassim, Saudi Arabia
;
