#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/87/2018767.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018767
loop_
_publ_author_name
'Yan, Xing-Chen'
'Fan, Yu-Hua'
'Bi, Cai-Feng'
'Zhang, Xia'
'Zhang, Zhong-Yu'
_publ_section_title
;
 An amino--imino resonance study of 2-amino-4-methylpyridinium nitrate and
 2-amino-5-methylpyridinium nitrate
;
_journal_coeditor_code           WQ3020
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              61
_journal_page_last               65
_journal_paper_doi               10.1107/S0108270112047877
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H9 N2 + , N O3 -'
_chemical_formula_moiety         'C6 H9 N2 +, N O3 -'
_chemical_formula_sum            'C6 H9 N3 O3'
_chemical_formula_weight         171.16
_chemical_name_systematic
;
2-amino-4-methylpyridinium nitrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4150(7)
_cell_length_b                   12.8669(11)
_cell_length_c                   15.2441(14)
_cell_measurement_reflns_used    1536
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.776
_cell_measurement_theta_min      2.673
_cell_volume                     1650.6(2)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7806
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.143
_refine_ls_extinction_coef       0.0052(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0487
_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)+(0.0379P)²+0.9001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                865
_reflns_number_total             1453
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wq3020.cif
_cod_data_source_block           I
_cod_database_code               2018767
_cod_database_fobs_code          2018767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
N N1 0.3102(3) 0.12928(18) 0.46825(16) 0.0534(7) Uani d . 1 1
H H1 0.233(4) 0.132(2) 0.427(2) 0.064 Uiso d . 1 1
N N2 0.5005(4) 0.1613(2) 0.36306(18) 0.0682(8) Uani d . 1 1
H H2A 0.425(4) 0.157(3) 0.322(2) 0.082 Uiso d . 1 1
H H2B 0.599(5) 0.149(3) 0.343(2) 0.082 Uiso d . 1 1
N N3 0.4582(3) 0.3718(2) 0.64011(17) 0.0578(7) Uani d . 1 1
O O1 0.5940(3) 0.3700(2) 0.67303(14) 0.0837(9) Uani d . 1 1
O O2 0.3422(2) 0.3620(2) 0.68888(14) 0.0809(8) Uani d . 1 1
O O3 0.4434(3) 0.3804(2) 0.56049(15) 0.0829(8) Uani d . 1 1
C C1 0.4630(3) 0.1419(2) 0.44629(18) 0.0471(7) Uani d . 1 1
C C2 0.5770(3) 0.1344(2) 0.51237(19) 0.0523(8) Uani d . 1 1
H H2C 0.682(4) 0.1403(19) 0.4941(18) 0.063 Uiso d . 1 1
C C3 0.5334(4) 0.1157(2) 0.59676(19) 0.0591(8) Uani d . 1 1
C C4 0.3729(5) 0.1030(3) 0.6157(2) 0.0719(10) Uani d . 1 1
H H4 0.345(4) 0.089(3) 0.672(2) 0.086 Uiso d . 1 1
C C5 0.2646(4) 0.1098(3) 0.5513(2) 0.0675(9) Uani d . 1 1
H H5 0.148(5) 0.104(2) 0.562(2) 0.081 Uiso d . 1 1
C C6 0.6562(5) 0.1077(3) 0.6686(2) 0.0929(13) Uani d . 1 1
H H6A 0.7605 0.1132 0.6436 0.139 Uiso calc R 1 1
H H6B 0.6456 0.0420 0.6978 0.139 Uiso calc R 1 1
H H6C 0.6404 0.1629 0.7101 0.139 Uiso calc R 1 1
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C1 N1 C5 122.1(3) yes
C1 N1 H1 121(2) yes
C5 N1 H1 117(2) yes
C1 N2 H2A 119(2) yes
C1 N2 H2B 121(2) yes
H2A N2 H2B 114(3) yes
O3 N3 O2 121.8(3) ?
O3 N3 O1 119.5(2) ?
O2 N3 O1 118.7(3) ?
N2 C1 N1 119.3(3) yes
N2 C1 C2 122.6(3) yes
N1 C1 C2 118.2(3) yes
C3 C2 C1 120.7(3) yes
C3 C2 H2C 123.7(18) ?
C1 C2 H2C 115.6(18) ?
C2 C3 C4 118.7(3) yes
C2 C3 C6 120.9(3) yes
C4 C3 C6 120.4(3) yes
C5 C4 C3 120.0(3) yes
C5 C4 H4 122(2) ?
C3 C4 H4 118(2) ?
C4 C5 N1 120.4(3) yes
C4 C5 H5 123(2) ?
N1 C5 H5 117(2) ?
C3 C6 H6A 109.5 ?
C3 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C3 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.338(4) yes
N1 C5 1.347(4) yes
N1 H1 0.90(3) yes
N2 C1 1.331(4) yes
N2 H2A 0.90(4) yes
N2 H2B 0.90(4) yes
N3 O3 1.225(3) ?
N3 O2 1.233(3) ?
N3 O1 1.248(3) ?
C1 C2 1.395(4) yes
C2 C3 1.359(4) yes
C2 H2C 0.93(3) ?
C3 C4 1.391(5) yes
C3 C6 1.509(4) yes
C4 C5 1.342(5) yes
C4 H4 0.91(3) ?
C5 H5 1.00(4) ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
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 O1 3_456 0.90(3) 1.92(3) 2.819(3) 171(3) yes
N1 H1 O3 3_456 0.90(3) 2.45(3) 3.120(3) 131(2) yes
N2 H2A O2 8_565 0.90(4) 2.16(4) 2.986(4) 153(3) yes
N2 H2B O2 3_556 0.90(4) 2.11(4) 2.998(4) 170(3) yes
C2 H2C O3 3_556 0.93(3) 2.36(3) 3.283(4) 168(2) yes
C4 H4 C6 6_557 0.91(3) 2.92(4) 3.760(5) 156(3) 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
C5 N1 C1 N2 -179.8(3)
C5 N1 C1 C2 -0.1(4)
N2 C1 C2 C3 179.2(3)
N1 C1 C2 C3 -0.5(4)
C1 C2 C3 C4 0.6(5)
C1 C2 C3 C6 -179.9(3)
C2 C3 C4 C5 -0.2(5)
C6 C3 C4 C5 -179.7(3)
C3 C4 C5 N1 -0.3(5)
C1 N1 C5 C4 0.5(5)
