##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2010-08-02
_journal_date_accepted     2010-08-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2362
_journal_page_last     o2362
_journal_paper_category     QO
_journal_coeditor_code     BX2300
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Mehmet Akkurt'
;
Department of Physics
Faculty of Sciences
Erciyes University
38039 Kayseri
Turkey
;
 'akkurt@erciyes.edu.tr'
    'Islam Ullah Khan'
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
 'iukhan.gcu@gmail.com'
_publ_contact_author_fax     '+90-352-4374933'
_publ_contact_author_phone     '+90-352-4374901 extra 33106'
_publ_section_title
;
2,4,6-Trimethylpyridinium nitrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Shahzad Sharif' .
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
    'Mehmet Akkurt' .
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Islam Ullah Khan' .
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
    'Abdul Rauf' .
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
    'Irfana Mariam' .
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
data_I
_chemical_name_systematic
;
2,4,6-Trimethylpyridinium nitrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H12 N +, N O3 -'
_chemical_formula_sum     'C8 H12 N2 O3'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C8 H12 N +, N O3 -'
_chemical_formula_weight     184.20
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'C m c m'
_symmetry_space_group_name_Hall     '-C 2c 2'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,1/2+z
    3 x,-y,-z
    4 -x,y,1/2-z
    5 -x,-y,-z
    6 x,y,1/2-z
    7 -x,y,z
    8 x,-y,1/2+z
    9 1/2+x,1/2+y,z
    10 1/2-x,1/2-y,1/2+z
    11 1/2+x,1/2-y,-z
    12 1/2-x,1/2+y,1/2-z
    13 1/2-x,1/2-y,-z
    14 1/2+x,1/2+y,1/2-z
    15 1/2-x,1/2+y,z
    16 1/2+x,1/2-y,1/2+z
_cell_length_a     9.3280(10)
_cell_length_b     15.1327(13)
_cell_length_c     6.4967(7)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     917.06(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     494
_cell_measurement_theta_min     4.0527
_cell_measurement_theta_max     23.1935
_cell_measurement_temperature     296(2)
_cell_special_details
;
;
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.07
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     392
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1839
_diffrn_reflns_av_R_equivalents     0.0302
_diffrn_reflns_av_sigmaI/netI     0.0404
_diffrn_reflns_theta_min     4.05
_diffrn_reflns_theta_max     28.29
_diffrn_reflns_theta_full     28.29
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     4
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs 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     648
_reflns_number_gt     410
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0813
_refine_ls_R_factor_gt     0.0466
_refine_ls_wR_factor_gt     0.1243
_refine_ls_wR_factor_ref     0.1487
_refine_ls_goodness_of_fit_ref     1.003
_refine_ls_restrained_S_all     0.999
_refine_ls_number_reflns     648
_refine_ls_number_parameters     58
_refine_ls_number_restraints     8
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0764P)²+0.2375P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.160
_refine_diff_density_min     -0.185
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    N N1 1.00000 0.13163(15) 0.25000 0.0411(8) Uani . . 1.000
    C C1 1.00000 0.4105(2) 0.25000 0.0604(13) Uani . . 1.000
    C C2 1.00000 0.31135(19) 0.25000 0.0444(10) Uani . . 1.000
    C C3 0.8725(2) 0.26452(14) 0.25000 0.0454(7) Uani . . 1.000
    C C4 0.8728(2) 0.17377(14) 0.25000 0.0422(7) Uani . . 1.000
    C C5 0.7402(3) 0.11973(17) 0.25000 0.0577(9) Uani . . 1.000
    O O1 0.50000 0.31452(15) 0.25000 0.0754(10) Uani . . 1.000
    O O2 0.6109(2) 0.43578(17) 0.25000 0.1128(13) Uani . . 1.000
    N N2 0.50000 0.39433(16) 0.25000 0.0469(9) Uani . . 1.000
    H H1 1.00000 0.0738(12) 0.25000 0.0560 Uiso . . 1.000
    H H1A 1.095(3) 0.435(4) 0.25000 0.0700 Uiso . . 0.500
    H H1B 0.949(3) 0.432(2) 0.369(4) 0.0700 Uiso . . 0.500
    H H3 0.7858(19) 0.2953(14) 0.25000 0.0560 Uiso . . 1.000
    H H5A 0.661(2) 0.1569(14) 0.25000 0.0700 Uiso . . 1.000
    H H5B 0.7366(19) 0.0801(10) 0.135(3) 0.0700 Uiso . . 1.000
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
    N1 0.0464(14) 0.0334(12) 0.0436(16) 0.0000 0.0000 0.0000
    C1 0.065(2) 0.0383(16) 0.078(3) 0.0000 0.0000 0.0000
    C2 0.0526(17) 0.0367(14) 0.044(2) 0.0000 0.0000 0.0000
    C3 0.0451(11) 0.0428(12) 0.0483(15) 0.0043(9) 0.0000 0.0000
    C4 0.0428(11) 0.0432(11) 0.0407(14) -0.0009(9) 0.0000 0.0000
    C5 0.0470(13) 0.0491(13) 0.077(2) -0.0054(10) 0.0000 0.0000
    O1 0.098(2) 0.0401(12) 0.088(2) 0.0000 0.0000 0.0000
    O2 0.0894(16) 0.1011(18) 0.148(3) -0.0507(13) 0.0000 0.0000
    N2 0.0526(15) 0.0461(15) 0.0420(17) 0.0000 0.0000 0.0000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 N2 . . 1.208(3) no
    O2 N2 . . 1.210(2) no
    N1 C4 . . 1.347(2) no
    N1 C4 . 4_755 1.347(2) no
    N1 H1 . . 0.875(18) no
    C1 C2 . . 1.500(4) no
    C2 C3 . 4_755 1.384(2) no
    C2 C3 . . 1.384(2) no
    C3 C4 . . 1.373(3) no
    C4 C5 . . 1.483(3) no
    C1 H1A . 4_755 0.96(4) no
    C1 H1A . . 0.96(4) no
    C1 H1B . . 0.96(3) no
    C1 H1B . 7_755 0.96(3) no
    C1 H1B . 4_755 0.96(3) no
    C1 H1B . 6_555 0.96(3) no
    C3 H3 . . 0.933(19) no
    C5 H5B . 6_555 0.959(18) no
    C5 H5A . . 0.93(2) no
    C5 H5B . . 0.959(18) no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    O2 N1 3.139(3) . 9_455 no
    O2 C5 3.111(4) . 12_655 no
    O2 N1 3.139(3) . 12_655 no
    O1 H3 2.682(18) . . no
    O1 H5A 2.82(2) . 4_655 no
    O1 H3 2.682(18) . . no
    O1 H5A 2.82(2) . . no
    O1 H3 2.682(18) . 4_655 no
    O1 H3 2.682(18) . 7_655 no
    O1 H5A 2.82(2) . 7_655 no
    O1 H5A 2.82(2) . . no
    O2 H1 2.331(16) . 9_455 no
    O2 H5B 2.888(19) . 10_655 no
    O2 H3 2.68(2) . . no
    O2 H1A 2.74(3) . 4_755 no
    O2 H3 2.68(2) . . no
    O2 H1A 2.74(3) . 4_755 no
    O2 H1 2.331(16) . 12_655 no
    O2 H5B 2.711(16) . 12_655 no
    N1 N2 3.2720(5) . 10_655 no
    N1 O2 3.139(3) . 9_545 no
    N1 N2 3.2720(5) . 10_654 no
    N1 N2 3.2720(5) . 13_656 no
    N1 O2 3.139(3) . 14_545 no
    N1 O2 3.139(3) . 15_645 no
    N1 N2 3.2720(5) . 16_554 no
    N1 N2 3.2720(5) . 16_555 no
    N1 O2 3.139(3) . 12_645 no
    N1 N2 3.2720(5) . 11_555 no
    N1 N2 3.2720(5) . 11_556 no
    N1 N2 3.2720(5) . 13_655 no
    N2 N1 3.2720(5) . 10_655 no
    N2 N1 3.2720(5) . 10_654 no
    N2 H1 2.716(18) . 9_455 no
    N2 H1 2.716(18) . 12_655 no
    C5 O2 3.111(4) . 15_645 no
    C5 O2 3.111(4) . 12_645 no
    H1 H5B 2.570(18) . 4_755 no
    H1 H5B 2.570(18) . 6_555 no
    H1 H5B 2.570(18) . . no
    H1 O2 2.331(16) . 9_545 no
    H1 N2 2.716(18) . 9_545 no
    H1 H5B 2.570(18) . 7_755 no
    H1 O2 2.331(16) . 14_545 no
    H1 O2 2.331(16) . 12_645 no
    H1 N2 2.716(18) . 12_645 no
    H1 N2 2.716(18) . 15_645 no
    H1 N2 2.716(18) . 14_545 no
    H1 O2 2.331(16) . 15_645 no
    H1A H3 2.39(6) . 4_755 no
    H1A O2 2.74(3) . 4_755 no
    H1A O2 2.74(3) . 7_755 no
    H1A H3 2.39(6) . 4_755 no
    H1B H5B 2.45(3) . 10_655 no
    H3 O1 2.682(18) . . no
    H3 O2 2.68(2) . . no
    H3 H5A 2.40(3) . . no
    H3 O1 2.682(18) . . no
    H3 O2 2.68(2) . . no
    H3 H1A 2.39(6) . 4_755 no
    H3 O1 2.682(18) . . no
    H3 O1 2.682(18) . . no
    H3 H1A 2.39(6) . 4_755 no
    H5A O1 2.82(2) . . no
    H5A O1 2.82(2) . . no
    H5A H3 2.40(3) . . no
    H5A O1 2.82(2) . . no
    H5A O1 2.82(2) . . no
    H5B O2 2.888(19) . 10_654 no
    H5B H1B 2.45(3) . 10_654 no
    H5B H1 2.570(18) . . no
    H5B O2 2.888(19) . 13_655 no
    H5B O2 2.711(16) . 15_645 no
    H5B O2 2.711(16) . 12_645 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4 N1 C4 . . 4_755 123.5(2) no
    C4 N1 H1 . . . 118.26(12) no
    C4 N1 H1 4_755 . . 118.26(12) no
    O2 N2 O2 . . 4_655 117.5(3) no
    O1 N2 O2 . . 4_655 121.23(15) no
    O1 N2 O2 . . . 121.23(15) no
    C1 C2 C3 . . . 120.79(13) no
    C1 C2 C3 . . 4_755 120.79(13) no
    C3 C2 C3 . . 4_755 118.4(2) no
    C2 C3 C4 . . . 120.67(19) no
    N1 C4 C5 . . . 118.3(2) no
    C3 C4 C5 . . . 123.35(19) no
    N1 C4 C3 . . . 118.37(18) no
    C2 C1 H1A . . 4_755 113(3) no
    C2 C1 H1B . . 4_755 109.7(18) no
    C2 C1 H1B . . 7_755 109.7(18) no
    H1A C1 H1B . . . 109(2) no
    C2 C1 H1B . . 6_555 109.7(18) no
    C2 C1 H1B . . . 109.7(18) no
    H1A C1 H1B . . 6_555 109(2) no
    H1A C1 H1B . . 7_755 54.2(17) no
    H1A C1 H1B 4_755 . . 54.2(17) no
    H1B C1 H1B . . 4_755 141(3) no
    H1B C1 H1B . . 6_555 107(2) no
    H1A C1 H1A . . 4_755 135(5) no
    H1A C1 H1B . . 4_755 54.2(17) no
    H1A C1 H1B 4_755 . 6_555 54.2(17) no
    H1A C1 H1B 4_755 . 7_755 109(2) no
    H1B C1 H1B 4_755 . 6_555 59(2) no
    H1B C1 H1B 4_755 . 7_755 107(2) no
    H1B C1 H1B 6_555 . 7_755 141(3) no
    C2 C1 H1A . . . 113(3) no
    H1B C1 H1B . . 7_755 59(2) no
    H1A C1 H1B 4_755 . 4_755 109(2) no
    C2 C3 H3 . . . 119.3(13) no
    C4 C3 H3 . . . 120.1(13) no
    C4 C5 H5B . . 6_555 112.0(11) no
    H5A C5 H5B . . 6_555 110.6(13) no
    H5B C5 H5B . . 6_555 102.4(15) no
    H5A C5 H5B . . . 110.6(13) no
    C4 C5 H5A . . . 109.2(13) no
    C4 C5 H5B . . . 112.0(11) no
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
    C1 C2 C3 C4 . . . . 180.00 no
    C2 C3 C4 N1 . . . . 0.00 no
    C2 C3 C4 C5 . . . . 180.00 no
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
    _geom_hbond_publ_flag
    N1 H1 O2 9_545 0.875(18) 2.331(16) 3.139(3) 153.7(2) yes
    N1 H1 O2 12_645 0.875(18) 2.331(16) 3.139(3) 153.7(2) yes
