#------------------------------------------------------------------------------
#$Date: 2016-08-27 04:51:42 +0300 (Sat, 27 Aug 2016) $
#$Revision: 186053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/39/1543987.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_1543987
loop_
_publ_author_name
'Sivakumar, P.'
'Devi, R. Niranjana'
'Israel, S.'
'Chakkaravarthi, G.'
_publ_section_title
;
 2-Amino-3-methylpyridinium 3,4-dimethoxybenzoate
;
_journal_coeditor_code           HB4072
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x161332
_journal_paper_doi               10.1107/S2414314616013328
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C6 H9 N2 + , C9 H9 O4 -'
_chemical_formula_moiety         'C9 H9 O4, C6 H9 N2'
_chemical_formula_sum            'C15 H18 N2 O4'
_chemical_formula_weight         290.31
_chemical_name_systematic
;
2-Amino-3-methylpyridinium 3,4-dimethoxybenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.000(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6972(8)
_cell_length_b                   6.6637(5)
_cell_length_c                   19.2325(17)
_cell_measurement_reflns_used    4375
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.5
_cell_volume                     1460.7(2)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17370
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         2.17
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0483
_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)+(0.0509P)²+0.5181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                2388
_reflns_number_total             3587
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb4072sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1543987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C C1 0.41591(14) -0.5512(3) 1.29093(10) 0.0411(4) Uani d . 1 1
H H1 0.4753 -0.4995 1.2711 0.049 Uiso calc R 1 1
C C2 0.43583(16) -0.7179(3) 1.33117(11) 0.0469(5) Uani d . 1 1
H H2 0.5086 -0.7810 1.3404 0.056 Uiso calc R 1 1
C C3 0.34363(16) -0.7937(3) 1.35878(11) 0.0463(5) Uani d . 1 1
H H3 0.3562 -0.9089 1.3868 0.056 Uiso calc R 1 1
C C4 0.23615(15) -0.7048(3) 1.34609(9) 0.0372(4) Uani d . 1 1
C C5 0.22031(13) -0.5260(2) 1.30491(9) 0.0320(4) Uani d . 1 1
C C6 0.13643(17) -0.7891(3) 1.37408(11) 0.0519(5) Uani d . 1 1
H H6A 0.0757 -0.8340 1.3349 0.078 Uiso calc R 1 1
H H6B 0.1058 -0.6871 1.4001 0.078 Uiso calc R 1 1
H H6C 0.1639 -0.9002 1.4051 0.078 Uiso calc R 1 1
C C7 0.21553(13) -0.8319(2) 1.14744(9) 0.0308(4) Uani d . 1 1
C C8 0.12877(14) -0.6888(3) 1.13558(10) 0.0384(4) Uani d . 1 1
H H8 0.0636 -0.7047 1.1552 0.046 Uiso calc R 1 1
C C9 0.13749(15) -0.5203(3) 1.09443(10) 0.0437(4) Uani d . 1 1
H H9 0.0783 -0.4242 1.0870 0.052 Uiso calc R 1 1
C C10 0.23282(15) -0.4946(2) 1.06465(9) 0.0382(4) Uani d . 1 1
C C11 0.32175(14) -0.6394(2) 1.07619(9) 0.0357(4) Uani d . 1 1
C C12 0.31268(14) -0.8051(2) 1.11728(9) 0.0335(4) Uani d . 1 1
H H12 0.3721 -0.9008 1.1251 0.040 Uiso calc R 1 1
C C13 0.1576(2) -0.1972(3) 1.00187(13) 0.0630(6) Uani d . 1 1
H H13A 0.0883 -0.2660 0.9770 0.094 Uiso calc R 1 1
H H13B 0.1795 -0.0982 0.9710 0.094 Uiso calc R 1 1
H H13C 0.1421 -0.1326 1.0434 0.094 Uiso calc R 1 1
C C14 0.49645(19) -0.7559(3) 1.04719(14) 0.0650(7) Uani d . 1 1
H H14A 0.5383 -0.7744 1.0957 0.098 Uiso calc R 1 1
H H14B 0.5505 -0.7192 1.0185 0.098 Uiso calc R 1 1
H H14C 0.4577 -0.8787 1.0295 0.098 Uiso calc R 1 1
C C15 0.20866(13) -1.0170(2) 1.19126(9) 0.0334(4) Uani d . 1 1
N N1 0.31064(12) -0.4576(2) 1.27889(8) 0.0357(3) Uani d D 1 1
N N2 0.12124(12) -0.4201(2) 1.29070(8) 0.0437(4) Uani d . 1 1
H H2A 0.1166 -0.3122 1.2657 0.052 Uiso calc R 1 1
H H2B 0.0619 -0.4597 1.3065 0.052 Uiso calc R 1 1
O O1 0.29953(10) -1.12424(18) 1.20672(7) 0.0466(3) Uani d . 1 1
O O2 0.11498(10) -1.05519(19) 1.20953(7) 0.0475(4) Uani d . 1 1
O O3 0.24997(13) -0.3368(2) 1.02274(8) 0.0570(4) Uani d . 1 1
O O4 0.41272(11) -0.60306(19) 1.04403(8) 0.0512(4) Uani d . 1 1
H H1A 0.3010(17) -0.345(2) 1.2541(10) 0.057(6) Uiso d D 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
C2 C1 N1 120.86(17)
C2 C1 H1 119.6
N1 C1 H1 119.6
C1 C2 C3 117.92(17)
C1 C2 H2 121.0
C3 C2 H2 121.0
C4 C3 C2 122.30(18)
C4 C3 H3 118.8
C2 C3 H3 118.8
C3 C4 C5 117.70(16)
C3 C4 C6 122.29(17)
C5 C4 C6 120.01(16)
N2 C5 N1 117.63(15)
N2 C5 C4 123.89(15)
N1 C5 C4 118.48(15)
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C12 118.78(15)
C8 C7 C15 122.07(14)
C12 C7 C15 119.15(14)
C7 C8 C9 120.60(16)
C7 C8 H8 119.7
C9 C8 H8 119.7
C10 C9 C8 120.54(16)
C10 C9 H9 119.7
C8 C9 H9 119.7
O3 C10 C9 125.60(16)
O3 C10 C11 114.93(15)
C9 C10 C11 119.47(16)
O4 C11 C12 124.78(15)
O4 C11 C10 115.62(15)
C12 C11 C10 119.59(15)
C11 C12 C7 121.02(15)
C11 C12 H12 119.5
C7 C12 H12 119.5
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O4 C14 H14A 109.5
O4 C14 H14B 109.5
H14A C14 H14B 109.5
O4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O2 C15 O1 124.38(16)
O2 C15 C7 118.98(14)
O1 C15 C7 116.63(14)
C5 N1 C1 122.70(16)
C5 N1 H1A 118.3(14)
C1 N1 H1A 119.0(14)
C5 N2 H2A 120.0
C5 N2 H2B 120.0
H2A N2 H2B 120.0
C10 O3 C13 117.98(16)
C11 O4 C14 117.25(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.344(3)
C1 N1 1.353(2)
C1 H1 0.9300
C2 C3 1.399(3)
C2 H2 0.9300
C3 C4 1.361(2)
C3 H3 0.9300
C4 C5 1.420(2)
C4 C6 1.499(2)
C5 N2 1.331(2)
C5 N1 1.346(2)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.374(2)
C7 C12 1.399(2)
C7 C15 1.506(2)
C8 C9 1.390(3)
C8 H8 0.9300
C9 C10 1.374(2)
C9 H9 0.9300
C10 O3 1.367(2)
C10 C11 1.399(2)
C11 O4 1.367(2)
C11 C12 1.376(2)
C12 H12 0.9300
C13 O3 1.414(2)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 O4 1.405(2)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 O2 1.2499(18)
C15 O1 1.2597(19)
N1 H1A 0.881(9)
N2 H2A 0.8600
N2 H2B 0.8600
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 H1A O1 1_565 0.883(15) 1.729(15) 2.6071(19) 173(2) y
N2 H2A O2 1_565 0.86 2.02 2.8816(19) 177 y
N2 H2B O2 2_557 0.86 2.12 2.9051(19) 152 y
C14 H14B O4 3_647 0.96 2.54 3.281(3) 134 y
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
N1 C1 C2 C3 1.4(3)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -1.8(3)
C2 C3 C4 C6 178.35(19)
C3 C4 C5 N2 -177.50(17)
C6 C4 C5 N2 2.4(3)
C3 C4 C5 N1 2.0(2)
C6 C4 C5 N1 -178.12(16)
C12 C7 C8 C9 -0.1(3)
C15 C7 C8 C9 -179.54(16)
C7 C8 C9 C10 0.3(3)
C8 C9 C10 O3 179.19(17)
C8 C9 C10 C11 -0.2(3)
O3 C10 C11 O4 -0.1(2)
C9 C10 C11 O4 179.35(16)
O3 C10 C11 C12 -179.59(16)
C9 C10 C11 C12 -0.1(3)
O4 C11 C12 C7 -179.09(16)
C10 C11 C12 C7 0.4(3)
C8 C7 C12 C11 -0.2(3)
C15 C7 C12 C11 179.22(15)
C8 C7 C15 O2 9.6(3)
C12 C7 C15 O2 -169.85(16)
C8 C7 C15 O1 -170.75(16)
C12 C7 C15 O1 9.8(2)
N2 C5 N1 C1 178.94(16)
C4 C5 N1 C1 -0.6(2)
C2 C1 N1 C5 -1.1(3)
C9 C10 O3 C13 -6.7(3)
C11 C10 O3 C13 172.67(17)
C12 C11 O4 C14 6.9(3)
C10 C11 O4 C14 -172.55(18)

_cod_database_fobs_code 1543987
