##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     ' SHELXL97 (Sheldrick, 2008)'
_journal_date_recd_electronic     2011-09-19
_journal_date_accepted     2011-09-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o2794
_journal_page_last     o2794
_journal_paper_category     QO
_journal_coeditor_code     FJ2453
_publ_contact_author_name     'Dr Graham Smith'
_publ_contact_author_address
;
    Faculty of Science and Technology
    Queensland University of Technology
    GPO Box 2434, Brisbane, Qld 4001, Australia
;
_publ_contact_author_email     g.smith@qut.edu.au
_publ_contact_author_fax     ' 61 7 3138 1804 '
_publ_contact_author_phone     ' 61 7 3300 2667 '
_publ_section_title
;
4-Aminopyridinium cis-2-carboxycyclohexane-1-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Graham Smith'
;
  Faculty of Science and Technology
  Queensland University of Technology
  GPO Box 2434, Brisbane, Queensland 4001, Australia
;
    ' Urs D. Wermuth '
;
  Faculty of Science and Technology
  Queensland University of Technology
  GPO Box 2434, Brisbane, Queensland 4001, Australia
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-Aminopyridinium cis-2-carboxycyclohexane-1-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H7 N2 +, C8 H11 O4 -'
_chemical_formula_sum     'C13 H18 N2 O4'
_chemical_formula_iupac     'C5 H7 N2 +, C8 H11 O4 -'
_chemical_formula_weight     266.29
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
_cell_length_a     12.1359(3)
_cell_length_b     9.8351(3)
_cell_length_c     11.1850(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1335.02(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4840
_cell_measurement_theta_min     3.22
_cell_measurement_theta_max     28.72
_cell_measurement_temperature     200(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.325
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_absorpt_correction_T_min     0.948
_exptl_absorpt_correction_T_max     0.990
_exptl_special_details     ?
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     16.077
_diffrn_reflns_number     9670
_diffrn_reflns_av_R_equivalents     0.0294
_diffrn_reflns_av_sigmaI/netI     0.0280
_diffrn_reflns_theta_min     3.23
_diffrn_reflns_theta_max     28.79
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.936
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1709
_reflns_number_gt     1448
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0369
_refine_ls_R_factor_gt     0.0278
_refine_ls_wR_factor_gt     0.0580
_refine_ls_wR_factor_ref     0.0595
_refine_ls_goodness_of_fit_ref     0.988
_refine_ls_restrained_S_all     0.988
_refine_ls_number_reflns     1709
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0357P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.148
_refine_diff_density_min     -0.162
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement
                      'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'PLATON (Spek, 2009)'
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
    O O11 -0.08623(9) 0.42384(12) 0.16082(11) 0.0293(4) Uani . . 1.000
    O O12 0.08627(8) 0.38250(12) 0.21757(10) 0.0262(3) Uani . . 1.000
    O O21 0.01171(10) 0.40723(12) 0.51058(12) 0.0285(3) Uani . . 1.000
    O O22 0.17703(9) 0.30714(12) 0.50187(12) 0.0296(3) Uani . . 1.000
    C C1 -0.06239(12) 0.25883(16) 0.31330(14) 0.0202(4) Uani . . 1.000
    C C2 0.02258(13) 0.20096(16) 0.40246(15) 0.0223(5) Uani . . 1.000
    C C3 0.10393(14) 0.10098(18) 0.34520(18) 0.0311(5) Uani . . 1.000
    C C4 0.04378(15) -0.01169(19) 0.2767(2) 0.0410(6) Uani . . 1.000
    C C5 -0.03704(15) 0.04676(19) 0.18597(18) 0.0340(6) Uani . . 1.000
    C C6 -0.11879(14) 0.14099(17) 0.24603(17) 0.0272(5) Uani . . 1.000
    C C11 -0.01574(12) 0.36284(16) 0.22481(14) 0.0200(5) Uani . . 1.000
    C C21 0.07930(13) 0.30994(17) 0.47466(14) 0.0222(5) Uani . . 1.000
    N N1A 0.16603(12) 0.28917(15) 0.99803(15) 0.0301(4) Uani . . 1.000
    N N41A 0.30073(13) 0.14997(18) 0.68510(15) 0.0320(5) Uani . . 1.000
    C C2A 0.14635(14) 0.35553(19) 0.89470(16) 0.0306(5) Uani . . 1.000
    C C3A 0.18908(13) 0.31222(17) 0.78984(16) 0.0285(5) Uani . . 1.000
    C C4A 0.25659(12) 0.19462(16) 0.78670(15) 0.0236(5) Uani . . 1.000
    C C5A 0.27516(14) 0.12848(18) 0.89698(16) 0.0289(5) Uani . . 1.000
    C C6A 0.22940(14) 0.17671(18) 0.99826(17) 0.0309(5) Uani . . 1.000
    H H1 -0.11940 0.30510 0.36020 0.0240 Uiso calc R 1.000
    H H2 -0.02010 0.14740 0.46010 0.0270 Uiso calc R 1.000
    H H21 0.046(2) 0.473(3) 0.561(3) 0.069(8) Uiso . . 1.000
    H H31B 0.15200 0.14990 0.29080 0.0370 Uiso calc R 1.000
    H H32B 0.14940 0.06050 0.40700 0.0370 Uiso calc R 1.000
    H H41B 0.09730 -0.06800 0.23550 0.0490 Uiso calc R 1.000
    H H42B 0.00420 -0.06880 0.33280 0.0490 Uiso calc R 1.000
    H H51B 0.00320 0.09640 0.12510 0.0410 Uiso calc R 1.000
    H H52B -0.07640 -0.02690 0.14720 0.0410 Uiso calc R 1.000
    H H61B -0.16300 0.08910 0.30200 0.0330 Uiso calc R 1.000
    H H62B -0.16790 0.17830 0.18600 0.0330 Uiso calc R 1.000
    H H1A 0.1408(18) 0.319(2) 1.0674(19) 0.038(6) Uiso . . 1.000
    H H2A 0.10230 0.43290 0.89560 0.0370 Uiso calc R 1.000
    H H3A 0.17420 0.35960 0.71970 0.0340 Uiso calc R 1.000
    H H5A 0.31920 0.05120 0.89970 0.0350 Uiso calc R 1.000
    H H6A 0.24190 0.13130 1.06990 0.0370 Uiso calc R 1.000
    H H41A 0.3409(18) 0.078(2) 0.687(2) 0.047(6) Uiso . . 1.000
    H H42A 0.2841(16) 0.193(2) 0.615(2) 0.038(6) Uiso . . 1.000
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O11 0.0297(6) 0.0270(6) 0.0312(7) 0.0010(5) -0.0051(5) 0.0106(6)
    O12 0.0244(6) 0.0291(6) 0.0251(6) -0.0047(5) 0.0004(5) 0.0028(5)
    O21 0.0321(6) 0.0263(6) 0.0272(6) 0.0042(5) -0.0021(6) -0.0066(6)
    O22 0.0304(6) 0.0316(6) 0.0269(6) 0.0036(5) -0.0062(5) -0.0019(6)
    C1 0.0205(7) 0.0188(8) 0.0212(8) 0.0009(6) 0.0009(6) -0.0003(7)
    C2 0.0267(8) 0.0193(8) 0.0209(8) -0.0009(7) 0.0007(7) 0.0046(7)
    C3 0.0325(9) 0.0253(9) 0.0354(10) 0.0084(8) -0.0064(8) -0.0016(8)
    C4 0.0439(10) 0.0247(9) 0.0543(13) 0.0080(8) -0.0046(10) -0.0118(9)
    C5 0.0387(10) 0.0270(9) 0.0363(11) -0.0064(8) -0.0040(9) -0.0106(8)
    C6 0.0269(8) 0.0226(8) 0.0322(10) -0.0068(7) -0.0053(7) 0.0039(8)
    C11 0.0254(8) 0.0166(8) 0.0179(8) -0.0006(6) -0.0006(6) -0.0031(6)
    C21 0.0287(8) 0.0222(8) 0.0157(8) 0.0017(7) -0.0004(6) 0.0051(7)
    N1A 0.0318(7) 0.0344(8) 0.0240(8) 0.0016(6) 0.0021(7) -0.0067(8)
    N41A 0.0366(8) 0.0293(9) 0.0302(9) 0.0098(7) 0.0024(7) -0.0044(7)
    C2A 0.0324(9) 0.0258(9) 0.0335(10) 0.0077(8) 0.0012(8) -0.0007(9)
    C3A 0.0334(9) 0.0241(9) 0.0281(9) 0.0057(7) -0.0019(8) 0.0023(8)
    C4A 0.0225(7) 0.0209(8) 0.0275(9) -0.0010(6) -0.0021(7) -0.0032(8)
    C5A 0.0305(9) 0.0233(9) 0.0329(10) 0.0054(7) -0.0085(8) -0.0012(8)
    C6A 0.0334(9) 0.0328(9) 0.0264(9) -0.0001(8) -0.0080(8) 0.0013(9)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
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
    O11 C11 . . 1.2665(19) no
    O12 C11 . . 1.2556(18) no
    O21 C21 . . 1.323(2) no
    O22 C21 . . 1.2248(19) no
    O21 H21 . . 0.95(3) no
    N1A C6A . . 1.347(2) no
    N1A C2A . . 1.349(2) no
    N41A C4A . . 1.331(2) no
    N1A H1A . . 0.88(2) no
    N41A H41A . . 0.86(2) no
    N41A H42A . . 0.91(2) no
    C1 C2 . . 1.543(2) no
    C1 C11 . . 1.532(2) no
    C1 C6 . . 1.542(2) no
    C2 C3 . . 1.534(2) no
    C2 C21 . . 1.508(2) no
    C3 C4 . . 1.532(3) no
    C4 C5 . . 1.524(3) no
    C5 C6 . . 1.515(3) no
    C1 H1 . . 0.9800 no
    C2 H2 . . 0.9800 no
    C3 H32B . . 0.9700 no
    C3 H31B . . 0.9700 no
    C4 H42B . . 0.9700 no
    C4 H41B . . 0.9700 no
    C5 H51B . . 0.9700 no
    C5 H52B . . 0.9700 no
    C6 H61B . . 0.9700 no
    C6 H62B . . 0.9700 no
    C2A C3A . . 1.351(2) no
    C3A C4A . . 1.418(2) no
    C4A C5A . . 1.413(2) no
    C5A C6A . . 1.348(3) no
    C2A H2A . . 0.9300 no
    C3A H3A . . 0.9300 no
    C5A H5A . . 0.9300 no
    C6A H6A . . 0.9300 no
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
    C21 O21 H21 . . . 113.6(15) no
    C2A N1A C6A . . . 120.01(16) no
    C6A N1A H1A . . . 117.9(13) no
    C2A N1A H1A . . . 122.0(13) no
    H41A N41A H42A . . . 122(2) no
    C4A N41A H41A . . . 118.6(15) no
    C4A N41A H42A . . . 119.4(13) no
    C2 C1 C6 . . . 109.55(13) no
    C2 C1 C11 . . . 114.64(12) no
    C6 C1 C11 . . . 110.53(13) no
    C1 C2 C21 . . . 112.88(13) no
    C1 C2 C3 . . . 113.38(14) no
    C3 C2 C21 . . . 112.67(13) no
    C2 C3 C4 . . . 111.46(14) no
    C3 C4 C5 . . . 111.52(15) no
    C4 C5 C6 . . . 110.92(16) no
    C1 C6 C5 . . . 112.68(14) no
    O11 C11 C1 . . . 115.58(13) no
    O11 C11 O12 . . . 123.82(14) no
    O12 C11 C1 . . . 120.59(13) no
    O21 C21 C2 . . . 113.18(13) no
    O22 C21 C2 . . . 123.99(15) no
    O21 C21 O22 . . . 122.77(15) no
    C6 C1 H1 . . . 107.00 no
    C2 C1 H1 . . . 107.00 no
    C11 C1 H1 . . . 107.00 no
    C1 C2 H2 . . . 106.00 no
    C3 C2 H2 . . . 106.00 no
    C21 C2 H2 . . . 106.00 no
    C4 C3 H32B . . . 109.00 no
    H31B C3 H32B . . . 108.00 no
    C4 C3 H31B . . . 109.00 no
    C2 C3 H31B . . . 109.00 no
    C2 C3 H32B . . . 109.00 no
    C5 C4 H41B . . . 109.00 no
    C5 C4 H42B . . . 109.00 no
    C3 C4 H42B . . . 109.00 no
    C3 C4 H41B . . . 109.00 no
    H41B C4 H42B . . . 108.00 no
    C6 C5 H51B . . . 109.00 no
    C4 C5 H52B . . . 109.00 no
    C6 C5 H52B . . . 109.00 no
    H51B C5 H52B . . . 108.00 no
    C4 C5 H51B . . . 109.00 no
    C5 C6 H62B . . . 109.00 no
    H61B C6 H62B . . . 108.00 no
    C1 C6 H61B . . . 109.00 no
    C1 C6 H62B . . . 109.00 no
    C5 C6 H61B . . . 109.00 no
    N1A C2A C3A . . . 121.56(17) no
    C2A C3A C4A . . . 120.03(16) no
    N41A C4A C3A . . . 121.53(16) no
    C3A C4A C5A . . . 116.50(15) no
    N41A C4A C5A . . . 121.97(15) no
    C4A C5A C6A . . . 120.41(16) no
    N1A C6A C5A . . . 121.50(17) no
    N1A C2A H2A . . . 119.00 no
    C3A C2A H2A . . . 119.00 no
    C2A C3A H3A . . . 120.00 no
    C4A C3A H3A . . . 120.00 no
    C4A C5A H5A . . . 120.00 no
    C6A C5A H5A . . . 120.00 no
    N1A C6A H6A . . . 119.00 no
    C5A C6A H6A . . . 119.00 no
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
    C6A N1A C2A C3A . . . . -0.2(3) no
    C2A N1A C6A C5A . . . . 0.6(3) no
    C6 C1 C2 C3 . . . . 51.98(17) no
    C11 C1 C2 C21 . . . . 56.73(18) no
    C6 C1 C2 C21 . . . . -178.36(13) no
    C11 C1 C2 C3 . . . . -72.93(17) no
    C2 C1 C11 O11 . . . . -171.66(14) no
    C2 C1 C11 O12 . . . . 9.2(2) no
    C6 C1 C11 O11 . . . . 63.95(18) no
    C6 C1 C11 O12 . . . . -115.22(16) no
    C11 C1 C6 C5 . . . . 72.82(18) no
    C2 C1 C6 C5 . . . . -54.43(19) no
    C21 C2 C3 C4 . . . . 177.72(15) no
    C1 C2 C3 C4 . . . . -52.5(2) no
    C3 C2 C21 O21 . . . . 171.15(14) no
    C3 C2 C21 O22 . . . . -11.6(2) no
    C1 C2 C21 O21 . . . . 41.13(19) no
    C1 C2 C21 O22 . . . . -141.58(16) no
    C2 C3 C4 C5 . . . . 53.7(2) no
    C3 C4 C5 C6 . . . . -56.2(2) no
    C4 C5 C6 C1 . . . . 57.4(2) no
    N1A C2A C3A C4A . . . . -0.2(3) no
    C2A C3A C4A N41A . . . . -179.40(16) no
    C2A C3A C4A C5A . . . . 0.0(2) no
    N41A C4A C5A C6A . . . . 179.81(17) no
    C3A C4A C5A C6A . . . . 0.4(2) no
    C4A C5A C6A N1A . . . . -0.7(3) 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
    N1A H1A O12 1_556 0.88(2) 1.91(2) 2.795(2) 180(3) yes
    N41A H41A O12 3_545 0.86(2) 2.14(2) 2.989(2) 168(2) yes
    N41A H42A O22 . 0.91(2) 2.13(2) 2.974(2) 152.6(18) yes
    O21 H21 O11 2_565 0.95(3) 1.59(3) 2.5302(17) 170(3) yes
    C2A H2A O21 2_565 0.93 2.46 3.287(2) 149 no
    C3A H3A O22 . 0.93 2.49 3.225(2) 136 no
    C3A H3A O11 2_565 0.93 2.47 3.222(2) 138 no
    C6A H6A O11 4_556 0.93 2.38 3.048(2) 128 no
    C3 H31B O12 . 0.97 2.56 3.123(2) 117 no
