#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/71/2227198.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227198
loop_
_publ_author_name
'Quah, Ching Kheng'
'Fun, Hoong-Kun'
'Isloor, Arun M.'
'Isloor, Nishitha'
_publ_section_title
;
 Bis(4-aminopyridinium) sulfate monohydrate
;
_journal_coeditor_code           BT5310
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2250
_journal_page_last               o2251
_journal_paper_doi               10.1107/S1600536810030941
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C5 H7 N2 +, S O4 2-, H2 O'
_chemical_formula_moiety         '2(C5 H7 N2 +), O4 S 2-, H2 O'
_chemical_formula_sum            'C10 H16 N4 O5 S'
_chemical_formula_weight         304.33
_chemical_name_systematic
;
Bis(4-aminopyridinium) sulfate monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.3650(10)
_cell_angle_beta                 97.5340(10)
_cell_angle_gamma                95.3870(10)
_cell_formula_units_Z            2
_cell_length_a                   6.44340(10)
_cell_length_b                   8.41530(10)
_cell_length_c                   12.4488(2)
_cell_measurement_reflns_used    3597
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      3.13
_cell_volume                     661.022(17)
_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
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10717
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.546
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0398
_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)+(0.0441P)²+0.4122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                3279
_reflns_number_total             3839
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5310.cif
_cod_data_source_block           I
_cod_database_code               2227198
_cod_database_fobs_code          2227198
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S S1 0.41695(5) 0.12500(4) 0.29301(3) 0.01520(10) Uani d . 1 . .
O O4 0.28974(17) 0.13054(13) 0.38487(9) 0.0210(2) Uani d . 1 . .
O O3 0.52927(17) 0.28476(13) 0.29263(10) 0.0217(2) Uani d . 1 . .
O O2 0.56565(18) 0.00390(14) 0.30613(10) 0.0256(3) Uani d . 1 . .
O O1 0.27120(18) 0.08095(15) 0.18901(10) 0.0277(3) Uani d . 1 . .
N N2 -0.0310(2) 0.34101(15) 0.35023(11) 0.0172(2) Uani d . 1 . .
C C5 0.2971(2) 0.72142(18) 0.42897(12) 0.0182(3) Uani d . 1 . .
H H5A 0.4373 0.7607 0.4527 0.022 Uiso calc R 1 . .
N N1 0.1519(2) 0.82613(16) 0.41396(11) 0.0192(3) Uani d . 1 . .
C C3 0.0277(2) 0.49838(17) 0.37303(11) 0.0144(3) Uani d . 1 . .
C C2 -0.1204(2) 0.61239(18) 0.36079(12) 0.0168(3) Uani d . 1 . .
H H2A -0.2625 0.5775 0.3392 0.020 Uiso calc R 1 . .
O O1W 0.8386(2) 0.96841(16) 0.15025(14) 0.0355(3) Uani d . 1 . .
C C4 0.2413(2) 0.55943(17) 0.40997(11) 0.0160(3) Uani d . 1 . .
H H4A 0.3428 0.4891 0.4212 0.019 Uiso calc R 1 . .
C C1 -0.0540(2) 0.77280(18) 0.38069(12) 0.0189(3) Uani d . 1 . .
H H1A -0.1514 0.8467 0.3713 0.023 Uiso calc R 1 . .
C C2A 0.7722(12) 0.4735(7) 1.0588(7) 0.0238(7) Uani d P 0.568(4) A 1
H H2AA 0.8019 0.5311 1.1282 0.029 Uiso calc PR 0.568(4) A 1
C C1A 0.7613(4) 0.3094(4) 1.0482(3) 0.0238(7) Uani d P 0.568(4) A 1
H H1AA 0.7854 0.2567 1.1097 0.029 Uiso calc PR 0.568(4) A 1
C C5A 0.6790(11) 0.2982(7) 0.8591(6) 0.0237(11) Uani d P 0.568(4) A 1
H H5AA 0.6461 0.2370 0.7910 0.028 Uiso calc PR 0.568(4) A 1
C C4A 0.6891(9) 0.4594(7) 0.8661(5) 0.0175(10) Uani d P 0.568(4) A 1
H H4AA 0.6624 0.5082 0.8030 0.021 Uiso calc PR 0.568(4) A 1
N N2A 0.7527(4) 0.7162(3) 0.9771(2) 0.0185(6) Uani d P 0.568(4) A 1
H H2NA 0.7286 0.7515 0.9160 0.028 Uiso d PR 0.568(4) A 1
H H1NA 0.7770 0.7672 1.0350 0.028 Uiso d PR 0.568(4) A 1
C C3A 0.7401(4) 0.5559(4) 0.9691(2) 0.0134(6) Uani d P 0.568(4) A 1
N N1A 0.7155(4) 0.2243(4) 0.9482(3) 0.0263(7) Uani d P 0.568(4) A 1
H H1AB 0.7039 0.1217 0.9350 0.032 Uiso d PR 0.568(4) A 1
N N2B 0.7174(5) 0.1525(5) 0.9860(3) 0.0219(8) Uani d P 0.432(4) A 2
H H1NB 0.7542 0.1178 1.0500 0.033 Uiso d PR 0.432(4) A 2
H H2NB 0.7106 0.0855 0.9312 0.033 Uiso d PR 0.432(4) A 2
C C1B 0.7723(6) 0.5882(5) 1.0409(4) 0.0270(10) Uani d P 0.432(4) A 2
H H1BB 0.7821 0.6760 1.0868 0.040 Uiso d PR 0.432(4) A 2
N N1B 0.7377(5) 0.6283(6) 0.9395(4) 0.0257(9) Uani d P 0.432(4) A 2
H H1BA 0.7421 0.7279 0.9294 0.038 Uiso d PR 0.432(4) A 2
C C3B 0.7256(5) 0.3062(6) 0.9719(3) 0.0173(8) Uani d P 0.432(4) A 2
C C4B 0.6880(12) 0.3543(9) 0.8640(6) 0.0168(13) Uani d P 0.432(4) A 2
H H4BA 0.6584 0.2771 0.8030 0.020 Uiso calc PR 0.432(4) A 2
C C5B 0.6959(13) 0.5103(9) 0.8524(7) 0.0208(13) Uani d P 0.432(4) A 2
H H5BA 0.6721 0.5400 0.7824 0.025 Uiso calc PR 0.432(4) A 2
C C2B 0.7688(12) 0.4344(6) 1.0631(6) 0.0153(12) Uani d P 0.432(4) A 2
H H2BA 0.7932 0.4112 1.1347 0.018 Uiso calc PR 0.432(4) A 2
H H1W1 0.750(5) 0.985(4) 0.201(3) 0.067(9) Uiso d . 1 . .
H H2W1 0.963(5) 1.006(3) 0.172(2) 0.054(8) Uiso d . 1 . .
H H1N1 0.193(3) 0.929(3) 0.4163(18) 0.033(6) Uiso d . 1 . .
H H1N2 0.061(4) 0.275(3) 0.3623(17) 0.031(6) Uiso d . 1 . .
H H2N2 -0.163(3) 0.309(2) 0.3310(16) 0.023(5) 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'
S S 0.1246 0.1234 '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
O3 S1 O2 . . 110.89(7) ?
O3 S1 O1 . . 109.12(7) ?
O2 S1 O1 . . 109.99(7) ?
O3 S1 O4 . . 109.09(7) ?
O2 S1 O4 . . 109.35(7) ?
O1 S1 O4 . . 108.35(7) ?
C3 N2 H1N2 . . 119.4(15) ?
C3 N2 H2N2 . . 118.3(13) ?
H1N2 N2 H2N2 . . 121.9(19) ?
N1 C5 C4 . . 121.14(13) ?
N1 C5 H5A . . 119.4 ?
C4 C5 H5A . . 119.4 ?
C5 N1 C1 . . 120.88(13) ?
C5 N1 H1N1 . . 119.8(15) ?
C1 N1 H1N1 . . 118.7(14) ?
N2 C3 C4 . . 121.37(13) ?
N2 C3 C2 . . 121.41(13) ?
C4 C3 C2 . . 117.21(13) ?
C1 C2 H2A . . 120.0 ?
C3 C2 H2A . . 120.0 ?
H1W1 O1W H2W1 . . 114(3) ?
C5 C4 C3 . . 119.81(13) ?
C5 C4 H4A . . 120.1 ?
C3 C4 H4A . . 120.1 ?
N1 C1 C2 . . 120.94(14) ?
N1 C1 H1A . . 119.5 ?
C2 C1 H1A . . 119.5 ?
C1A C2A C3A . . 121.7(7) ?
C1A C2A H2AA . . 119.1 ?
C3A C2A H2AA . . 119.1 ?
N1A C1A C2A . . 119.7(5) ?
N1A C1A H1AA . . 120.1 ?
C2A C1A H1AA . . 120.1 ?
N1A C5A C4A . . 121.2(6) ?
N1A C5A H5AA . . 119.4 ?
C4A C5A H5AA . . 119.4 ?
C5A C4A C3A . . 120.6(5) ?
C5A C4A H4AA . . 119.7 ?
C3A C4A H4AA . . 119.7 ?
C3A N2A H2NA . . 113.5 ?
C3A N2A H1NA . . 119.5 ?
H2NA N2A H1NA . . 127.0 ?
C3A N2A H1BB . . 73.5 ?
H2NA N2A H1BB . . 172.0 ?
H1NA N2A H1BB . . 46.1 ?
C3A N2A H1BA . . 102.2 ?
H1NA N2A H1BA . . 138.1 ?
H1BB N2A H1BA . . 175.5 ?
N2A C3A C2A . . 122.9(4) ?
N2A C3A C4A . . 121.2(4) ?
C2A C3A C4A . . 115.9(4) ?
C2A C3A H1BA . . 145.0 ?
C4A C3A H1BA . . 99.1 ?
C5A N1A C1A . . 120.9(4) ?
C5A N1A H1AB . . 113.9 ?
C1A N1A H1AB . . 125.2 ?
C5A N1A H2NB . . 114.7 ?
C1A N1A H2NB . . 124.4 ?
C3B N2B H1AB . . 98.6 ?
C3B N2B H1NB . . 123.7 ?
H1AB N2B H1NB . . 136.0 ?
C3B N2B H2NB . . 117.9 ?
H1NB N2B H2NB . . 116.1 ?
N1B C1B C2B . . 123.4(5) ?
N1B C1B H1NA . . 65.4 ?
C2B C1B H1NA . . 171.1 ?
N1B C1B H1BB . . 108.0 ?
C2B C1B H1BB . . 128.3 ?
C1B N1B C5B . . 119.7(5) ?
C1B N1B H2NA . . 126.9 ?
C5B N1B H2NA . . 113.3 ?
C1B N1B H1BA . . 120.0 ?
C5B N1B H1BA . . 120.3 ?
N2B C3B C4B . . 120.9(5) ?
N2B C3B C2B . . 122.3(4) ?
C4B C3B C2B . . 116.8(5) ?
C4B C3B H1AB . . 96.6 ?
C2B C3B H1AB . . 146.6 ?
C5B C4B C3B . . 119.5(6) ?
C5B C4B H4BA . . 120.2 ?
C3B C4B H4BA . . 120.2 ?
C4B C5B N1B . . 122.4(7) ?
C4B C5B H5BA . . 118.8 ?
N1B C5B H5BA . . 118.8 ?
C1B C2B C3B . . 118.2(5) ?
C1B C2B H2BA . . 120.9 ?
C3B C2B H2BA . . 120.9 ?
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
S1 O3 . 1.4666(11) ?
S1 O2 . 1.4706(11) ?
S1 O1 . 1.4849(12) ?
S1 O4 . 1.4909(12) ?
N2 C3 . 1.3311(18) ?
N2 H1N2 . 0.86(2) ?
N2 H2N2 . 0.86(2) ?
C5 N1 . 1.354(2) ?
C5 C4 . 1.363(2) ?
C5 H5A . 0.9300 ?
N1 C1 . 1.355(2) ?
N1 H1N1 . 0.88(2) ?
C3 C4 . 1.4208(19) ?
C3 C2 . 1.421(2) ?
C2 C1 . 1.362(2) ?
C2 H2A . 0.9300 ?
O1W H1W1 . 0.91(3) ?
O1W H2W1 . 0.83(3) ?
C4 H4A . 0.9300 ?
C1 H1A . 0.9300 ?
C2A C1A . 1.366(6) ?
C2A C3A . 1.381(8) ?
C2A H2AA . 0.9300 ?
C1A N1A . 1.347(5) ?
C1A H1AA . 0.9300 ?
C5A N1A . 1.335(9) ?
C5A C4A . 1.345(5) ?
C5A H5AA . 0.9300 ?
C4A C3A . 1.422(6) ?
C4A H4AA . 0.9300 ?
N2A C3A . 1.335(4) ?
N2A H2NA . 0.8477 ?
N2A H1NA . 0.7856 ?
N1A H1AB . 0.8555 ?
N2B C3B . 1.321(6) ?
N2B H1NB . 0.8900 ?
N2B H2NB . 0.8295 ?
C1B N1B . 1.339(6) ?
C1B C2B . 1.352(6) ?
C1B H1BB . 0.8750 ?
N1B C5B . 1.367(11) ?
N1B H2NA . 1.1125 ?
N1B H1BA . 0.8600 ?
C3B C4B . 1.443(8) ?
C3B C2B . 1.456(8) ?
C4B C5B . 1.334(7) ?
C4B H4BA . 0.9300 ?
C5B H5BA . 0.9300 ?
C2B H2BA . 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
N2A H2NA O1 2_666 0.8500 2.0300 2.822(3) 156.00 yes
N2A H1NA O1W 1_556 0.7900 2.0700 2.812(3) 159.00 yes
N1A H1AB O1 2_656 0.8600 2.2000 2.938(4) 144.00 yes
O1W H1W1 O2 1_565 0.91(3) 1.88(3) 2.7952(19) 176(3) yes
O1W H2W1 O1 1_665 0.83(3) 2.00(3) 2.8195(18) 167(2) yes
N1 H1N1 O4 1_565 0.88(3) 1.85(2) 2.7102(17) 165(2) yes
N2 H1N2 O4 . 0.86(3) 2.01(3) 2.8665(17) 176(2) yes
N2 H2N2 O3 1_455 0.862(19) 1.96(2) 2.8118(17) 167.9(16) yes
C1 H1A O2 1_465 0.9300 2.4600 3.3688(18) 167.00 yes
C1A H1AA O1W 1_546 0.9300 2.5800 3.318(4) 137.00 yes
C5A H5AA O2 2_656 0.9300 2.4400 3.228(7) 143.00 yes
C4A H4AA O3 2_666 0.9300 2.5400 3.362(6) 147.00 yes
C5 H5A O4 2_666 0.9300 2.5200 3.3360(18) 146.00 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
C4 C5 N1 C1 . . . . 0.7(2) ?
N2 C3 C2 C1 . . . . -177.42(14) ?
C4 C3 C2 C1 . . . . 2.2(2) ?
N1 C5 C4 C3 . . . . 0.4(2) ?
N2 C3 C4 C5 . . . . 177.75(13) ?
C2 C3 C4 C5 . . . . -1.9(2) ?
C5 N1 C1 C2 . . . . -0.4(2) ?
C3 C2 C1 N1 . . . . -1.1(2) ?
C3A C2A C1A N1A . . . . -0.9(8) ?
N1A C5A C4A C3A . . . . 0.3(8) ?
C1A C2A C3A N2A . . . . -179.1(4) ?
C1A C2A C3A C4A . . . . 1.8(8) ?
C5A C4A C3A N2A . . . . 179.3(4) ?
C5A C4A C3A C2A . . . . -1.6(7) ?
C4A C5A N1A C1A . . . . 0.7(7) ?
C2A C1A N1A C5A . . . . -0.5(7) ?
C2B C1B N1B C5B . . . . 0.1(8) ?
N2B C3B C4B C5B . . . . 179.5(5) ?
C2B C3B C4B C5B . . . . 0.6(8) ?
C3B C4B C5B N1B . . . . -0.3(10) ?
C1B N1B C5B C4B . . . . 0.0(9) ?
N1B C1B C2B C3B . . . . 0.2(8) ?
N2B C3B C2B C1B . . . . -179.4(5) ?
C4B C3B C2B C1B . . . . -0.5(8) ?
