#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/71/2227121.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_2227121
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Hemamalini, Madhukar'
'Rajakannan, Venkatachalam'
_publ_section_title
;
 4-Aminopyridinium 4-carboxybutanoate
;
_journal_coeditor_code           WN2401
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2108
_journal_paper_doi               10.1107/S1600536810028734
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H7 N2 +, C5 H7 O4 -'
_chemical_formula_moiety         'C5 H7 N2 +, C5 H7 O4 -'
_chemical_formula_sum            'C10 H14 N2 O4'
_chemical_formula_weight         226.23
_chemical_name_systematic
;
4-Aminopyridinium 4-carboxybutanoate
;
_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                 102.1430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.6159(2)
_cell_length_b                   10.3065(2)
_cell_length_c                   22.6801(5)
_cell_measurement_reflns_used    8906
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      2.52
_cell_volume                     2197.45(8)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Bruker SMART APEXII 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7931
_diffrn_reflns_theta_full        32.58
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         1.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         7931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0758P)²+0.2205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                5556
_reflns_number_total             7931
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wn2401.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227121
_cod_database_fobs_code          2227121
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
O O1A 0.28193(16) 1.02435(13) 0.06872(6) 0.0516(3) Uani d . 1 . .
H H1O1 0.2530 1.0161 0.0289 0.077 Uiso d R 1 . .
O O2A 0.41099(16) 0.95000(13) 0.15319(5) 0.0478(3) Uani d . 1 . .
O O3A 0.76925(16) 0.49292(13) 0.05256(5) 0.0528(4) Uani d . 1 . .
O O4A 0.74003(16) 0.55719(12) 0.14167(5) 0.0454(3) Uani d . 1 . .
C C1A 0.3787(2) 0.94695(15) 0.09826(7) 0.0352(3) Uani d . 1 . .
C C2A 0.4485(2) 0.85513(16) 0.06135(7) 0.0370(3) Uani d . 1 . .
H H2AA 0.5028 0.9059 0.0381 0.044 Uiso calc R 1 . .
H H2AB 0.3745 0.8103 0.0330 0.044 Uiso calc R 1 . .
C C3A 0.5465(2) 0.75453(16) 0.09724(7) 0.0352(3) Uani d . 1 . .
H H3AA 0.6264 0.7976 0.1230 0.042 Uiso calc R 1 . .
H H3AB 0.4955 0.7064 0.1227 0.042 Uiso calc R 1 . .
C C4A 0.60070(19) 0.66165(16) 0.05536(7) 0.0366(3) Uani d . 1 . .
H H4AA 0.5202 0.6144 0.0322 0.044 Uiso calc R 1 . .
H H4AB 0.6415 0.7121 0.0271 0.044 Uiso calc R 1 . .
C C5A 0.7105(2) 0.56458(15) 0.08576(7) 0.0346(3) Uani d . 1 . .
N N1A 0.28175(17) 0.87243(15) 0.83697(7) 0.0449(4) Uani d . 1 . .
H H1AA 0.2264 0.9279 0.8486 0.054 Uiso calc R 1 . .
N N2A 0.53978(18) 0.60387(16) 0.78136(7) 0.0499(4) Uani d . 1 . .
H H2AC 0.5341 0.5918 0.7434 0.060 Uiso calc R 1 . .
H H2AD 0.5987 0.5590 0.8072 0.060 Uiso calc R 1 . .
C C6A 0.3744(2) 0.80430(19) 0.87789(8) 0.0488(4) Uani d . 1 . .
H H6AA 0.3778 0.8191 0.9186 0.059 Uiso calc R 1 . .
C C7A 0.4634(2) 0.71465(18) 0.86214(8) 0.0461(4) Uani d . 1 . .
H H7AA 0.5268 0.6692 0.8915 0.055 Uiso calc R 1 . .
C C8A 0.45783(19) 0.69135(17) 0.79991(8) 0.0379(3) Uani d . 1 . .
C C9A 0.3609(2) 0.76547(17) 0.75810(7) 0.0399(4) Uani d . 1 . .
H H9AA 0.3548 0.7543 0.7169 0.048 Uiso calc R 1 . .
C C10A 0.2754(2) 0.85416(19) 0.77826(8) 0.0434(4) Uani d . 1 . .
H H10A 0.2115 0.9027 0.7504 0.052 Uiso calc R 1 . .
O O1B 1.22169(16) -0.01002(13) 0.95900(5) 0.0527(4) Uani d . 1 . .
O O2B 1.10552(17) 0.05354(13) 0.86994(5) 0.0494(3) Uani d . 1 . .
O O3B 0.72084(16) 0.52422(13) 0.94174(6) 0.0532(4) Uani d . 1 . .
H H1O3 0.7347 0.5145 0.9828 0.080 Uiso d R 1 . .
O O4B 0.76125(17) 0.44368(13) 0.85744(5) 0.0524(3) Uani d . 1 . .
C C1B 1.12988(19) 0.06276(15) 0.92524(7) 0.0359(3) Uani d . 1 . .
C C2B 1.05243(19) 0.16092(15) 0.95600(7) 0.0357(3) Uani d . 1 . .
H H2BA 1.1223 0.2127 0.9831 0.043 Uiso calc R 1 . .
H H2BB 0.9966 0.1148 0.9803 0.043 Uiso calc R 1 . .
C C3B 0.9547(2) 0.25132(15) 0.91350(7) 0.0342(3) Uani d . 1 . .
H H3BA 0.8792 0.2016 0.8884 0.041 Uiso calc R 1 . .
H H3BB 1.0079 0.2948 0.8874 0.041 Uiso calc R 1 . .
C C4B 0.89090(19) 0.35155(16) 0.94935(7) 0.0361(3) Uani d . 1 . .
H H4BA 0.8441 0.3063 0.9773 0.043 Uiso calc R 1 . .
H H4BB 0.9677 0.4023 0.9731 0.043 Uiso calc R 1 . .
C C5B 0.7856(2) 0.44294(16) 0.91214(7) 0.0358(3) Uani d . 1 . .
N N1B -0.04752(17) 0.37734(15) 0.17394(7) 0.0453(4) Uani d . 1 . .
H H1BA -0.1137 0.4333 0.1619 0.054 Uiso calc R 1 . .
N N2B 0.26087(18) 0.10594(16) 0.23042(7) 0.0494(4) Uani d . 1 . .
H H2BC 0.2914 0.0928 0.2684 0.059 Uiso calc R 1 . .
H H2BD 0.2946 0.0613 0.2046 0.059 Uiso calc R 1 . .
C C6B 0.0019(2) 0.35827(19) 0.23332(8) 0.0440(4) Uani d . 1 . .
H H6BA -0.0348 0.4067 0.2611 0.053 Uiso calc R 1 . .
C C7B 0.1058(2) 0.26829(17) 0.25317(7) 0.0402(4) Uani d . 1 . .
H H7BA 0.1392 0.2560 0.2943 0.048 Uiso calc R 1 . .
C C8B 0.16224(19) 0.19448(17) 0.21178(7) 0.0377(3) Uani d . 1 . .
C C9B 0.1092(2) 0.21875(18) 0.14972(8) 0.0463(4) Uani d . 1 . .
H H9BA 0.1444 0.1734 0.1206 0.056 Uiso calc R 1 . .
C C10B 0.0059(2) 0.30944(19) 0.13355(8) 0.0494(5) Uani d . 1 . .
H H10B -0.0291 0.3250 0.0927 0.059 Uiso calc R 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
C1A O1A H1O1 . . 120.0 ?
O2A C1A O1A . . 120.78(15) ?
O2A C1A C2A . . 122.33(15) ?
O1A C1A C2A . . 116.89(13) ?
C1A C2A C3A . . 115.41(12) ?
C1A C2A H2AA . . 108.4 ?
C3A C2A H2AA . . 108.4 ?
C1A C2A H2AB . . 108.4 ?
C3A C2A H2AB . . 108.4 ?
H2AA C2A H2AB . . 107.5 ?
C4A C3A C2A . . 110.61(12) ?
C4A C3A H3AA . . 109.5 ?
C2A C3A H3AA . . 109.5 ?
C4A C3A H3AB . . 109.5 ?
C2A C3A H3AB . . 109.5 ?
H3AA C3A H3AB . . 108.1 ?
C5A C4A C3A . . 115.55(13) ?
C5A C4A H4AA . . 108.4 ?
C3A C4A H4AA . . 108.4 ?
C5A C4A H4AB . . 108.4 ?
C3A C4A H4AB . . 108.4 ?
H4AA C4A H4AB . . 107.5 ?
O4A C5A O3A . . 122.35(15) ?
O4A C5A C4A . . 119.61(14) ?
O3A C5A C4A . . 118.04(13) ?
C10A N1A C6A . . 120.06(16) ?
C10A N1A H1AA . . 120.0 ?
C6A N1A H1AA . . 120.0 ?
C8A N2A H2AC . . 120.0 ?
C8A N2A H2AD . . 120.0 ?
H2AC N2A H2AD . . 120.0 ?
N1A C6A C7A . . 122.55(17) ?
N1A C6A H6AA . . 118.7 ?
C7A C6A H6AA . . 118.7 ?
C6A C7A C8A . . 118.83(17) ?
C6A C7A H7AA . . 120.6 ?
C8A C7A H7AA . . 120.6 ?
N2A C8A C9A . . 120.67(16) ?
N2A C8A C7A . . 122.04(16) ?
C9A C8A C7A . . 117.29(16) ?
C10A C9A C8A . . 119.73(16) ?
C10A C9A H9AA . . 120.1 ?
C8A C9A H9AA . . 120.1 ?
N1A C10A C9A . . 121.52(17) ?
N1A C10A H10A . . 119.2 ?
C9A C10A H10A . . 119.2 ?
C5B O3B H1O3 . . 117.8 ?
O2B C1B O1B . . 121.54(15) ?
O2B C1B C2B . . 121.05(14) ?
O1B C1B C2B . . 117.40(13) ?
C1B C2B C3B . . 114.68(13) ?
C1B C2B H2BA . . 108.6 ?
C3B C2B H2BA . . 108.6 ?
C1B C2B H2BB . . 108.6 ?
C3B C2B H2BB . . 108.6 ?
H2BA C2B H2BB . . 107.6 ?
C2B C3B C4B . . 110.07(12) ?
C2B C3B H3BA . . 109.6 ?
C4B C3B H3BA . . 109.6 ?
C2B C3B H3BB . . 109.6 ?
C4B C3B H3BB . . 109.6 ?
H3BA C3B H3BB . . 108.2 ?
C5B C4B C3B . . 115.13(13) ?
C5B C4B H4BA . . 108.5 ?
C3B C4B H4BA . . 108.5 ?
C5B C4B H4BB . . 108.5 ?
C3B C4B H4BB . . 108.5 ?
H4BA C4B H4BB . . 107.5 ?
O4B C5B O3B . . 120.63(15) ?
O4B C5B C4B . . 122.68(15) ?
O3B C5B C4B . . 116.69(13) ?
C10B N1B C6B . . 120.21(16) ?
C10B N1B H1BA . . 119.9 ?
C6B N1B H1BA . . 119.9 ?
C8B N2B H2BC . . 120.0 ?
C8B N2B H2BD . . 120.0 ?
H2BC N2B H2BD . . 120.0 ?
N1B C6B C7B . . 120.57(17) ?
N1B C6B H6BA . . 119.7 ?
C7B C6B H6BA . . 119.7 ?
C6B C7B C8B . . 120.38(16) ?
C6B C7B H7BA . . 119.8 ?
C8B C7B H7BA . . 119.8 ?
N2B C8B C7B . . 120.90(15) ?
N2B C8B C9B . . 121.69(16) ?
C7B C8B C9B . . 117.41(16) ?
C10B C9B C8B . . 118.75(17) ?
C10B C9B H9BA . . 120.6 ?
C8B C9B H9BA . . 120.6 ?
N1B C10B C9B . . 122.66(17) ?
N1B C10B H10B . . 118.7 ?
C9B C10B H10B . . 118.7 ?
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
O1A C1A . 1.299(2) ?
O1A H1O1 . 0.8903 ?
O2A C1A . 1.2194(18) ?
O3A C5A . 1.269(2) ?
O4A C5A . 1.2423(18) ?
C1A C2A . 1.511(2) ?
C2A C3A . 1.518(2) ?
C2A H2AA . 0.9700 ?
C2A H2AB . 0.9700 ?
C3A C4A . 1.516(2) ?
C3A H3AA . 0.9700 ?
C3A H3AB . 0.9700 ?
C4A C5A . 1.511(2) ?
C4A H4AA . 0.9700 ?
C4A H4AB . 0.9700 ?
N1A C10A . 1.333(2) ?
N1A C6A . 1.342(2) ?
N1A H1AA . 0.8600 ?
N2A C8A . 1.323(2) ?
N2A H2AC . 0.8600 ?
N2A H2AD . 0.8600 ?
C6A C7A . 1.357(3) ?
C6A H6AA . 0.9300 ?
C7A C8A . 1.422(2) ?
C7A H7AA . 0.9300 ?
C8A C9A . 1.407(2) ?
C9A C10A . 1.370(3) ?
C9A H9AA . 0.9300 ?
C10A H10A . 0.9300 ?
O1B C1B . 1.2823(19) ?
O2B C1B . 1.2303(19) ?
O3B C5B . 1.310(2) ?
O3B H1O3 . 0.9176 ?
O4B C5B . 1.2133(19) ?
C1B C2B . 1.511(2) ?
C2B C3B . 1.516(2) ?
C2B H2BA . 0.9700 ?
C2B H2BB . 0.9700 ?
C3B C4B . 1.521(2) ?
C3B H3BA . 0.9700 ?
C3B H3BB . 0.9700 ?
C4B C5B . 1.505(2) ?
C4B H4BA . 0.9700 ?
C4B H4BB . 0.9700 ?
N1B C10B . 1.338(2) ?
N1B C6B . 1.345(2) ?
N1B H1BA . 0.8600 ?
N2B C8B . 1.320(2) ?
N2B H2BC . 0.8600 ?
N2B H2BD . 0.8600 ?
C6B C7B . 1.368(3) ?
C6B H6BA . 0.9300 ?
C7B C8B . 1.403(2) ?
C7B H7BA . 0.9300 ?
C8B C9B . 1.415(2) ?
C9B C10B . 1.357(3) ?
C9B H9BA . 0.9300 ?
C10B H10B . 0.9300 ?
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
O1A H1O1 O1B 1_464 0.8900 1.5700 2.4591(17) 172.00 yes
N1A H1AA O1B 1_465 0.8600 2.5900 3.183(2) 127.00 yes
N1A H1AA O2B 1_465 0.8600 1.8700 2.729(2) 177.00 yes
N2A H2AC O2A 4_576 0.8600 2.1800 2.9627(19) 151.00 yes
N2A H2AD O4B . 0.8600 2.1000 2.948(2) 170.00 yes
O3B H1O3 O3A 1_556 0.9200 1.5600 2.4791(17) 176.00 yes
C10A H10A O4B 2_656 0.9300 2.5500 3.161(2) 124.00 yes
C7A H7AA O3B . 0.9300 2.4700 3.370(2) 162.00 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
O2A C1A C2A C3A . . . . 8.1(3) ?
O1A C1A C2A C3A . . . . -172.34(16) ?
C1A C2A C3A C4A . . . . 175.44(15) ?
C2A C3A C4A C5A . . . . 174.42(15) ?
C3A C4A C5A O4A . . . . 6.7(3) ?
C3A C4A C5A O3A . . . . -173.38(17) ?
C10A N1A C6A C7A . . . . -0.6(3) ?
N1A C6A C7A C8A . . . . -0.3(3) ?
C6A C7A C8A N2A . . . . -178.87(18) ?
C6A C7A C8A C9A . . . . 1.1(3) ?
N2A C8A C9A C10A . . . . 178.99(18) ?
C7A C8A C9A C10A . . . . -1.0(3) ?
C6A N1A C10A C9A . . . . 0.8(3) ?
C8A C9A C10A N1A . . . . 0.1(3) ?
O2B C1B C2B C3B . . . . -4.8(3) ?
O1B C1B C2B C3B . . . . 175.08(17) ?
C1B C2B C3B C4B . . . . -175.99(14) ?
C2B C3B C4B C5B . . . . -176.94(15) ?
C3B C4B C5B O4B . . . . -5.5(3) ?
C3B C4B C5B O3B . . . . 175.12(16) ?
C10B N1B C6B C7B . . . . -0.9(3) ?
N1B C6B C7B C8B . . . . 0.0(3) ?
C6B C7B C8B N2B . . . . -178.91(18) ?
C6B C7B C8B C9B . . . . 1.0(3) ?
N2B C8B C9B C10B . . . . 178.79(18) ?
C7B C8B C9B C10B . . . . -1.1(3) ?
C6B N1B C10B C9B . . . . 0.8(3) ?
C8B C9B C10B N1B . . . . 0.3(3) ?
