##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-02-25
_journal_date_accepted     2009-02-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      4
_journal_page_first     o748
_journal_page_last     o749
_journal_paper_category     QO
_journal_coeditor_code     AT2732
_publ_contact_author_name     'Prof. Fun Hoong Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
Bis(4-aminopyridinium) bis(hydrogen oxalate) monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hoong-Kun Fun' .
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Jain John' .
;
      Department of Physics
      National Institute of Technology
      Tiruchirappalli 620015
      India
;
    'Samuel Robinson Jebas'
;
      Permanent address:
      Department of Physics,
      Karunya University,
      Karunya Nagar,
      Coimbatore 641114,
      India.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Balasubramanian, T' .
;
      Department of Physics
      National Institute of Technology
      Tiruchirappalli 620015
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis(4-aminopyridinium) bis(hydrogen oxalate) monohydrate
;
_chemical_name_common     '4-aminopyridinium oxalate'
_chemical_formula_moiety     '2C5 H7 N2 + , 2C2 H O4 - , H2 O'
_chemical_formula_sum     'C14 H18 N4 O9'
_chemical_formula_weight     386.32
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     15.6429(6)
_cell_length_b     5.6929(2)
_cell_length_c     19.9091(7)
_cell_angle_alpha     90.00
_cell_angle_beta     105.617(2)
_cell_angle_gamma     90.00
_cell_volume     1707.52(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7009
_cell_measurement_theta_min     2.70
_cell_measurement_theta_max     38.77
_cell_measurement_temperature     100
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.503
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     808
_exptl_absorpt_coefficient_mu     0.127
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9061
_exptl_absorpt_correction_T_max     0.9859
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K.
;
_diffrn_ambient_temperature     100
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     12438
_diffrn_reflns_av_R_equivalents     0.0270
_diffrn_reflns_av_sigmaI/netI     0.0205
_diffrn_reflns_theta_min     2.12
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     28
_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     2467
_reflns_number_gt     2159
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0392
_refine_ls_R_factor_gt     0.0340
_refine_ls_wR_factor_gt     0.0910
_refine_ls_wR_factor_ref     0.0958
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     2467
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0564P)²+0.8323P] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     0.351
_refine_diff_density_min     -0.243
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and 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_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.50462(4) -0.16951(12) 0.39445(3) 0.01643(15) Uani d . 1 . .
    O O2 0.59652(5) -0.02380(12) 0.49260(3) 0.01700(16) Uani d . 1 . .
    O O3 0.55682(5) 0.41624(12) 0.44228(4) 0.02023(17) Uani d . 1 . .
    O O4 0.45356(5) 0.26647(12) 0.35138(3) 0.01903(16) Uani d . 1 . .
    N N1 0.18206(5) 0.86694(16) 0.57611(4) 0.01960(18) Uani d . 1 . .
    N N2 0.39056(6) 1.06075(16) 0.74035(4) 0.01829(17) Uani d . 1 . .
    C C1 0.20886(7) 0.72101(18) 0.63132(5) 0.0199(2) Uani d . 1 . .
    C C2 0.27784(6) 0.77998(18) 0.68707(5) 0.01844(19) Uani d . 1 . .
    C C3 0.32276(6) 0.99712(16) 0.68737(5) 0.01467(18) Uani d . 1 . .
    C C4 0.29134(6) 1.14587(17) 0.62850(5) 0.01667(19) Uani d . 1 . .
    C C5 0.22175(6) 1.07631(18) 0.57489(5) 0.0188(2) Uani d . 1 . .
    C C6 0.54297(6) 0.00122(16) 0.43617(4) 0.01357(17) Uani d . 1 . .
    C C7 0.51411(6) 0.25017(16) 0.40655(5) 0.01471(18) Uani d . 1 . .
    O O1W 0.5000 0.46896(19) 0.7500 0.0215(2) Uani d S 1 . .
    H H2W1 0.5135(12) 0.560(3) 0.7190(9) 0.048(5) Uiso d . 1 . .
    H H1 0.1765(9) 0.574(3) 0.6285(7) 0.028(3) Uiso d . 1 . .
    H H2 0.2966(9) 0.673(3) 0.7268(8) 0.029(4) Uiso d . 1 . .
    H H4 0.3195(9) 1.295(3) 0.6250(7) 0.023(3) Uiso d . 1 . .
    H H5 0.1983(9) 1.169(2) 0.5344(7) 0.021(3) Uiso d . 1 . .
    H H1N2 0.4086(10) 0.968(3) 0.7766(8) 0.028(4) Uiso d . 1 . .
    H H2N2 0.4168(9) 1.197(3) 0.7367(7) 0.025(3) Uiso d . 1 . .
    H H1N1 0.1413(11) 0.823(3) 0.5397(9) 0.038(4) Uiso d . 1 . .
    H H1O1 0.5253(12) -0.327(4) 0.4140(9) 0.054(5) Uiso d . 1 . .
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
    O1 0.0207(3) 0.0102(3) 0.0151(3) 0.0000(2) -0.0007(2) -0.0013(2)
    O2 0.0197(3) 0.0137(3) 0.0141(3) 0.0009(2) -0.0014(3) 0.0004(2)
    O3 0.0259(4) 0.0109(3) 0.0186(3) -0.0014(2) -0.0033(3) -0.0011(2)
    O4 0.0249(4) 0.0141(3) 0.0136(3) 0.0010(2) -0.0027(3) 0.0007(2)
    N1 0.0176(4) 0.0215(4) 0.0160(4) -0.0005(3) -0.0017(3) -0.0030(3)
    N2 0.0178(4) 0.0182(4) 0.0152(4) -0.0017(3) -0.0019(3) 0.0011(3)
    C1 0.0196(4) 0.0165(5) 0.0221(5) -0.0023(3) 0.0031(4) -0.0012(3)
    C2 0.0192(4) 0.0166(4) 0.0176(4) -0.0011(3) 0.0017(3) 0.0028(3)
    C3 0.0149(4) 0.0143(4) 0.0140(4) 0.0012(3) 0.0022(3) -0.0006(3)
    C4 0.0177(4) 0.0143(4) 0.0165(4) 0.0008(3) 0.0019(3) 0.0017(3)
    C5 0.0182(4) 0.0205(5) 0.0152(4) 0.0032(3) 0.0002(3) 0.0025(3)
    C6 0.0158(4) 0.0112(4) 0.0133(4) -0.0001(3) 0.0032(3) -0.0002(3)
    C7 0.0188(4) 0.0112(4) 0.0132(4) 0.0003(3) 0.0027(3) 0.0002(3)
    O1W 0.0307(6) 0.0146(5) 0.0188(5) 0.000 0.0061(4) 0.000
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    O1 C6 . 1.3139(11) ?
    O1 H1O1 . 1.00(2) ?
    O2 C6 . 1.2155(11) ?
    O3 C7 . 1.2611(11) ?
    O4 C7 . 1.2458(11) ?
    N1 C5 . 1.3471(14) ?
    N1 C1 . 1.3514(13) ?
    N1 H1N1 . 0.863(17) ?
    N2 C3 . 1.3291(12) ?
    N2 H1N2 . 0.877(15) ?
    N2 H2N2 . 0.890(16) ?
    C1 C2 . 1.3654(13) ?
    C1 H1 . 0.973(15) ?
    C2 C3 . 1.4211(13) ?
    C2 H2 . 0.979(15) ?
    C3 C4 . 1.4221(12) ?
    C4 C5 . 1.3621(13) ?
    C4 H4 . 0.966(15) ?
    C5 H5 . 0.951(13) ?
    C6 C7 . 1.5547(13) ?
    O1W H2W1 . 0.874(18) ?
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
    C6 O1 H1O1 . . 111.9(11) ?
    C5 N1 C1 . . 121.00(8) ?
    C5 N1 H1N1 . . 118.7(11) ?
    C1 N1 H1N1 . . 120.2(11) ?
    C3 N2 H1N2 . . 120.1(10) ?
    C3 N2 H2N2 . . 117.4(9) ?
    H1N2 N2 H2N2 . . 122.5(13) ?
    N1 C1 C2 . . 120.95(9) ?
    N1 C1 H1 . . 116.1(8) ?
    C2 C1 H1 . . 123.0(8) ?
    C1 C2 C3 . . 119.93(9) ?
    C1 C2 H2 . . 120.2(9) ?
    C3 C2 H2 . . 119.9(9) ?
    N2 C3 C2 . . 121.90(9) ?
    N2 C3 C4 . . 121.12(9) ?
    C2 C3 C4 . . 116.98(8) ?
    C5 C4 C3 . . 119.91(9) ?
    C5 C4 H4 . . 118.8(8) ?
    C3 C4 H4 . . 121.3(8) ?
    N1 C5 C4 . . 121.21(9) ?
    N1 C5 H5 . . 115.6(8) ?
    C4 C5 H5 . . 123.2(9) ?
    O2 C6 O1 . . 125.55(8) ?
    O2 C6 C7 . . 121.00(8) ?
    O1 C6 C7 . . 113.45(7) ?
    O4 C7 O3 . . 127.09(8) ?
    O4 C7 C6 . . 118.46(8) ?
    O3 C7 C6 . . 114.44(8) ?
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 C2 . . . . -0.98(15) ?
    N1 C1 C2 C3 . . . . -0.29(15) ?
    C1 C2 C3 N2 . . . . -179.57(9) ?
    C1 C2 C3 C4 . . . . 1.08(14) ?
    N2 C3 C4 C5 . . . . 179.98(9) ?
    C2 C3 C4 C5 . . . . -0.67(14) ?
    C1 N1 C5 C4 . . . . 1.41(15) ?
    C3 C4 C5 N1 . . . . -0.56(15) ?
    O2 C6 C7 O4 . . . . -173.95(8) ?
    O1 C6 C7 O4 . . . . 6.47(12) ?
    O2 C6 C7 O3 . . . . 6.58(13) ?
    O1 C6 C7 O3 . . . . -173.00(8) ?
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
    O1W H2W1 O4 5_666 0.874(18) 1.895(18) 2.7676(9) 175.0(18)
    N2 H1N2 O4 6_566 0.877(15) 1.983(16) 2.8556(11) 173.4(14)
    N2 H2N2 O1W 1_565 0.890(16) 1.993(15) 2.8620(12) 164.8(13)
    N1 H1N1 O3 3_455 0.863(17) 2.100(17) 2.8645(11) 147.3(15)
    N1 H1N1 O2 3_455 0.863(17) 2.218(17) 2.8818(11) 133.6(15)
    O1 H1O1 O3 1_545 1.00(2) 1.60(2) 2.5916(10) 177.6(18)
    C5 H5 O2 3_465 0.951(13) 2.361(14) 3.1585(12) 141.2(11)
