#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227292.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227292
loop_
_publ_author_name
'Sharif, Shahzad'
'Akkurt, Mehmet'
'Khan, Islam Ullah'
'Rauf, Abdul'
'Mariam, Irfana'
_publ_section_title
;
 2,4,6-Trimethylpyridinium nitrate
;
_journal_coeditor_code           BX2300
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2362
_journal_paper_doi               10.1107/S1600536810032629
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H12 N +, N O3 -'
_chemical_formula_moiety         'C8 H12 N +, N O3 -'
_chemical_formula_sum            'C8 H12 N2 O3'
_chemical_formula_weight         184.20
_chemical_name_systematic
;
2,4,6-Trimethylpyridinium nitrate
;
_space_group_IT_number           63
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2c 2'
_symmetry_space_group_name_H-M   'C m c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3280(10)
_cell_length_b                   15.1327(13)
_cell_length_c                   6.4967(7)
_cell_measurement_reflns_used    494
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.1935
_cell_measurement_theta_min      4.0527
_cell_volume                     917.06(16)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1839
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         4.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         648
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0764P)²+0.2375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                410
_reflns_number_total             648
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2300.cif
_cod_data_source_block           I
_cod_database_code               2227292
_cod_database_fobs_code          2227292
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
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_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'
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_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_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
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
