#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/71/2227119.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_2227119
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-4-methylpyridinium (E)-3-carboxyprop-2-enoate
;
_journal_coeditor_code           WN2399
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1962
_journal_page_last               o1963
_journal_paper_doi               10.1107/S1600536810026292
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H9 N2 +, C4 H3 O4 -'
_chemical_formula_moiety         'C6 H9 N2 +, C4 H3 O4 -'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22
_chemical_name_common
;
2-Amino-4-methylpyridinium hydrogen fumarate
;
_chemical_name_systematic
;
2-amino-4-methylpyridinium (E)-3-carboxyprop-2-enoate
;
_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                 108.332(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0058(16)
_cell_length_b                   19.814(7)
_cell_length_c                   11.286(4)
_cell_measurement_reflns_used    2803
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.01
_cell_measurement_theta_min      2.80
_cell_volume                     1062.6(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12900
_diffrn_reflns_theta_full        31.06
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1060P)²+0.0446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1675
_reflns_number_gt                2573
_reflns_number_total             3387
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2399.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227119
_cod_database_fobs_code          2227119
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_disorder_assembly
_atom_site_disorder_group
N N1 -0.1142(2) 0.80864(6) 0.55566(10) 0.0138(2) Uani d . 1 . .
N N2 0.0376(2) 0.76324(6) 0.75413(11) 0.0166(2) Uani d . 1 . .
C C1 0.0731(3) 0.80768(7) 0.67234(11) 0.0129(3) Uani d . 1 . .
C C2 0.2978(3) 0.85492(7) 0.70188(12) 0.0143(3) Uani d . 1 . .
C C3 0.3220(3) 0.90042(7) 0.61461(12) 0.0153(3) Uani d . 1 . .
C C4 0.1210(3) 0.89903(7) 0.49325(12) 0.0176(3) Uani d . 1 . .
C C5 -0.0911(3) 0.85296(7) 0.46726(12) 0.0159(3) Uani d . 1 . .
C C6 0.5539(3) 0.95182(8) 0.64658(13) 0.0198(3) Uani d . 1 . .
O O1 0.4413(2) 0.77430(5) -0.00598(9) 0.0167(2) Uani d . 1 . .
O O2 0.5841(2) 0.82660(5) 0.17910(9) 0.0187(2) Uani d . 1 . .
O O3 -0.33328(19) 0.94128(5) -0.04434(9) 0.0170(2) Uani d . 1 . .
O O4 -0.2087(2) 0.98609(5) 0.14785(9) 0.0184(2) Uani d . 1 . .
C C7 0.4153(3) 0.81746(7) 0.07303(11) 0.0129(3) Uani d . 1 . .
C C8 0.1559(3) 0.86036(7) 0.03171(12) 0.0144(3) Uani d . 1 . .
C C9 0.0841(3) 0.90251(7) 0.10791(12) 0.0150(3) Uani d . 1 . .
C C10 -0.1721(3) 0.94438(7) 0.06278(12) 0.0132(3) Uani d . 1 . .
H H1O4 -0.368(4) 1.0119(9) 0.1114(16) 0.020 Uiso d . 1 . .
H H1N1 -0.278(4) 0.7781(9) 0.5333(16) 0.016 Uiso d . 1 . .
H H1N2 -0.124(4) 0.7315(9) 0.7264(16) 0.016 Uiso d . 1 . .
H H2N2 0.141(4) 0.7622(9) 0.8262(17) 0.016 Uiso d . 1 . .
H H2A 0.428(4) 0.8529(9) 0.7855(16) 0.016 Uiso d . 1 . .
H H4A 0.137(4) 0.9308(9) 0.4299(16) 0.016 Uiso d . 1 . .
H H5A -0.244(3) 0.8495(9) 0.3834(15) 0.016 Uiso d . 1 . .
H H6A 0.655(4) 0.9509(10) 0.5852(16) 0.020 Uiso d . 1 . .
H H6B 0.683(4) 0.9461(9) 0.7285(17) 0.020 Uiso d . 1 . .
H H6C 0.457(4) 0.9960(10) 0.6385(16) 0.020 Uiso d . 1 . .
H H8A 0.029(4) 0.8563(9) -0.0593(16) 0.016 Uiso d . 1 . .
H H9A 0.198(4) 0.9063(9) 0.1949(16) 0.016 Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C5 . . 121.94(11) ?
C1 N1 H1N1 . . 120.4(10) ?
C5 N1 H1N1 . . 117.6(10) ?
C1 N2 H1N2 . . 118.4(10) ?
C1 N2 H2N2 . . 121.9(13) ?
H1N2 N2 H2N2 . . 119.7(16) ?
N2 C1 N1 . . 118.80(11) ?
N2 C1 C2 . . 122.92(12) ?
N1 C1 C2 . . 118.27(11) ?
C3 C2 C1 . . 120.53(12) ?
C3 C2 H2A . . 123.2(11) ?
C1 C2 H2A . . 116.3(11) ?
C2 C3 C4 . . 119.00(12) ?
C2 C3 C6 . . 120.72(12) ?
C4 C3 C6 . . 120.28(12) ?
C5 C4 C3 . . 119.24(12) ?
C5 C4 H4A . . 121.0(10) ?
C3 C4 H4A . . 119.7(11) ?
C4 C5 N1 . . 121.02(12) ?
C4 C5 H5A . . 123.7(10) ?
N1 C5 H5A . . 115.3(10) ?
C3 C6 H6A . . 110.5(11) ?
C3 C6 H6B . . 112.9(11) ?
H6A C6 H6B . . 110.0(16) ?
C3 C6 H6C . . 105.0(11) ?
H6A C6 H6C . . 107.3(15) ?
H6B C6 H6C . . 110.9(15) ?
C10 O4 H1O4 . . 108.6(11) ?
O2 C7 O1 . . 125.82(12) ?
O2 C7 C8 . . 118.51(11) ?
O1 C7 C8 . . 115.67(11) ?
C9 C8 C7 . . 122.70(12) ?
C9 C8 H8A . . 119.2(10) ?
C7 C8 H8A . . 118.1(10) ?
C8 C9 C10 . . 120.85(12) ?
C8 C9 H9A . . 120.8(11) ?
C10 C9 H9A . . 118.3(11) ?
O3 C10 O4 . . 123.28(12) ?
O3 C10 C9 . . 122.87(11) ?
O4 C10 C9 . . 113.83(11) ?
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 . 1.3553(16) ?
N1 C5 . 1.3611(17) ?
N1 H1N1 . 0.987(18) ?
N2 C1 . 1.3276(17) ?
N2 H1N2 . 0.994(18) ?
N2 H2N2 . 0.816(19) ?
C1 C2 . 1.4202(18) ?
C2 C3 . 1.3683(18) ?
C2 H2A . 0.964(17) ?
C3 C4 . 1.4219(19) ?
C3 C6 . 1.5006(19) ?
C4 C5 . 1.3604(19) ?
C4 H4A . 0.976(17) ?
C5 H5A . 1.015(17) ?
C6 H6A . 0.977(18) ?
C6 H6B . 0.953(19) ?
C6 H6C . 0.991(19) ?
O1 C7 . 1.2714(15) ?
O2 C7 . 1.2424(16) ?
O3 C10 . 1.2259(16) ?
O4 C10 . 1.3224(15) ?
O4 H1O4 . 0.93(2) ?
C7 C8 . 1.4987(18) ?
C8 C9 . 1.3269(18) ?
C8 H8A . 1.027(17) ?
C9 C10 . 1.4769(18) ?
C9 H9A . 0.970(18) ?
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
O4 H1O4 O3 3_475 0.928(19) 1.720(19) 2.6472(17) 179(2) yes
N1 H1N1 O1 4_476 0.987(18) 1.689(18) 2.6761(16) 179.5(17) yes
N2 H1N2 O2 4_476 0.994(18) 1.804(18) 2.7979(16) 179.0(16) yes
N2 H2N2 O1 1_556 0.816(19) 2.028(19) 2.8320(18) 168.5(18) yes
C2 H2A O3 1_656 0.964(18) 2.596(18) 3.349(2) 135.1(14) yes
C5 H5A O2 1_455 1.015(16) 2.239(16) 3.189(2) 155.0(13) yes
C6 H6B O3 1_656 0.954(19) 2.592(19) 3.360(2) 137.8(16) 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
C5 N1 C1 N2 . . . . 179.79(12) ?
C5 N1 C1 C2 . . . . 0.38(18) ?
N2 C1 C2 C3 . . . . -178.88(12) ?
N1 C1 C2 C3 . . . . 0.51(19) ?
C1 C2 C3 C4 . . . . -1.0(2) ?
C1 C2 C3 C6 . . . . 178.11(12) ?
C2 C3 C4 C5 . . . . 0.5(2) ?
C6 C3 C4 C5 . . . . -178.53(13) ?
C3 C4 C5 N1 . . . . 0.3(2) ?
C1 N1 C5 C4 . . . . -0.8(2) ?
O2 C7 C8 C9 . . . . -7.3(2) ?
O1 C7 C8 C9 . . . . 172.67(13) ?
C7 C8 C9 C10 . . . . 179.34(11) ?
C8 C9 C10 O3 . . . . 2.0(2) ?
C8 C9 C10 O4 . . . . -177.01(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656171
