#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229097.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_2229097
loop_
_publ_author_name
'Zhu, Zhi-Biao'
'Gao, Shan'
'Ng, Seik Weng'
_publ_section_title
;
 4-Aminopyridinium-3-sulfonate monohydrate
;
_journal_coeditor_code           IM2250
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o456
_journal_paper_doi               10.1107/S1600536811002145
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H6 N2 O3 S, H2 O'
_chemical_formula_moiety         'C5 H6 N2 O3 S, H2 O'
_chemical_formula_sum            'C5 H8 N2 O4 S'
_chemical_formula_weight         192.19
_chemical_name_systematic
;
4-Aminopyridinium-3-sulfonate monohydrate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.6739(13)
_cell_length_b                   6.5824(3)
_cell_length_c                   7.3204(3)
_cell_measurement_reflns_used    13913
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1526.23(11)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22965
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  0.9387
_exptl_absorpt_correction_T_min  0.9207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1898
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0795P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                1325
_reflns_number_total             1898
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2250.cif
_cod_data_source_block           I
_cod_database_code               2229097
_cod_database_fobs_code          2229097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
S S1 0.55812(2) 0.2500 0.86929(9) 0.0348(3) Uani d S 1 . .
S S2 0.66689(2) 0.2500 0.36003(10) 0.0360(3) Uani d S 1 . .
O O1 0.58140(6) 0.4293(3) 0.8206(3) 0.0647(6) Uani d . 1 . .
O O2 0.54212(8) 0.2500 1.0518(3) 0.0712(10) Uani d S 1 . .
O O1W 0.62156(8) 0.7500 1.0095(3) 0.0451(6) Uani d SD 1 . .
H H1W 0.6107(9) 0.648(4) 0.959(4) 0.068 Uiso d D 1 . .
O O2W 0.67561(10) -0.2500 0.6401(4) 0.0573(8) Uani d SD 1 . .
H H2W 0.6649(10) -0.151(4) 0.582(4) 0.086 Uiso d D 1 . .
O O3 0.64409(5) 0.0686(3) 0.4112(2) 0.0496(5) Uani d . 1 . .
O O4 0.68205(8) 0.2500 0.1750(3) 0.0570(8) Uani d S 1 . .
N N1 0.43845(8) 0.2500 0.7058(4) 0.0413(7) Uani d SD 1 . .
H H1 0.4151(7) 0.2500 0.770(4) 0.050 Uiso d SD 1 . .
N N2 0.55273(8) 0.2500 0.4434(3) 0.0366(7) Uani d SD 1 . .
H H21 0.5763(6) 0.2500 0.505(4) 0.044 Uiso d SD 1 . .
H H22 0.5522(11) 0.2500 0.3234(14) 0.044 Uiso d SD 1 . .
N N3 0.78781(8) 0.2500 0.5065(4) 0.0416(7) Uani d SD 1 . .
H H3 0.8121(6) 0.2500 0.449(4) 0.050 Uiso d SD 1 . .
N N4 0.67536(8) 0.2500 0.7841(4) 0.0443(8) Uani d SD 1 . .
H H41 0.6504(6) 0.2500 0.731(5) 0.053 Uiso d SD 1 . .
H H42 0.6752(12) 0.2500 0.9046(15) 0.053 Uiso d SD 1 . .
C C1 0.47379(9) 0.2500 0.8053(4) 0.0367(8) Uani d S 1 . .
H H1A 0.4717 0.2500 0.9320 0.044 Uiso calc SR 1 . .
C C2 0.51300(9) 0.2500 0.7265(4) 0.0296(7) Uani d S 1 . .
C C3 0.51604(9) 0.2500 0.5320(4) 0.0285(7) Uani d S 1 . .
C C4 0.47767(9) 0.2500 0.4337(4) 0.0330(7) Uani d S 1 . .
H H4 0.4783 0.2500 0.3067 0.040 Uiso calc SR 1 . .
C C5 0.44023(11) 0.2500 0.5209(4) 0.0408(8) Uani d S 1 . .
H H5 0.4153 0.2500 0.4535 0.049 Uiso calc SR 1 . .
C C6 0.78747(10) 0.2500 0.6914(5) 0.0449(9) Uani d S 1 . .
H H6 0.8129 0.2500 0.7549 0.054 Uiso calc SR 1 . .
C C7 0.75061(10) 0.2500 0.7851(4) 0.0399(8) Uani d S 1 . .
H H7 0.7510 0.2500 0.9121 0.048 Uiso calc SR 1 . .
C C8 0.71128(9) 0.2500 0.6911(4) 0.0344(7) Uani d S 1 . .
C C9 0.71321(10) 0.2500 0.4964(4) 0.0332(7) Uani d S 1 . .
C C10 0.75175(10) 0.2500 0.4121(4) 0.0368(8) Uani d S 1 . .
H H10 0.7529 0.2500 0.2852 0.044 Uiso calc SR 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
O2 S1 O1 . . 114.46(10) ?
O2 S1 O1 . 7_565 114.46(10) ?
O1 S1 O1 . 7_565 110.5(2) ?
O2 S1 C2 . . 105.40(14) ?
O1 S1 C2 . . 105.54(9) ?
O1 S1 C2 7_565 . 105.54(9) ?
O4 S2 O3 . . 114.29(9) ?
O4 S2 O3 . 7_565 114.29(9) ?
O3 S2 O3 . 7_565 111.47(16) ?
O4 S2 C9 . . 104.71(14) ?
O3 S2 C9 . . 105.51(8) ?
O3 S2 C9 7_565 . 105.51(8) ?
C1 N1 C5 . . 120.7(3) ?
C1 N1 H1 . . 114(2) ?
C5 N1 H1 . . 125(2) ?
C3 N2 H21 . . 120(2) ?
C3 N2 H22 . . 118(2) ?
H21 N2 H22 . . 122(3) ?
C10 N3 C6 . . 120.7(3) ?
C10 N3 H3 . . 120(2) ?
C6 N3 H3 . . 119(2) ?
C8 N4 H41 . . 123(3) ?
C8 N4 H42 . . 121(3) ?
H41 N4 H42 . . 116(4) ?
N1 C1 C2 . . 122.0(3) ?
N1 C1 H1A . . 119.0 ?
C2 C1 H1A . . 119.0 ?
C1 C2 C3 . . 118.8(3) ?
C1 C2 S1 . . 118.9(2) ?
C3 C2 S1 . . 122.3(2) ?
N2 C3 C4 . . 120.2(2) ?
N2 C3 C2 . . 123.0(3) ?
C4 C3 C2 . . 116.8(3) ?
C5 C4 C3 . . 121.1(3) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 N1 . . 120.7(3) ?
C4 C5 H5 . . 119.7 ?
N1 C5 H5 . . 119.7 ?
N3 C6 C7 . . 120.9(3) ?
N3 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C6 C7 C8 . . 120.7(3) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
N4 C8 C7 . . 120.2(3) ?
N4 C8 C9 . . 123.4(3) ?
C7 C8 C9 . . 116.4(3) ?
C10 C9 C8 . . 119.3(3) ?
C10 C9 S2 . . 119.0(2) ?
C8 C9 S2 . . 121.8(2) ?
N3 C10 C9 . . 122.0(3) ?
N3 C10 H10 . . 119.0 ?
C9 C10 H10 . . 119.0 ?
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 O2 . 1.429(2) ?
S1 O1 . 1.436(2) ?
S1 O1 7_565 1.436(2) ?
S1 C2 . 1.771(3) ?
S2 O4 . 1.437(2) ?
S2 O3 . 1.4451(18) ?
S2 O3 7_565 1.4451(18) ?
S2 C9 . 1.775(3) ?
O1W H1W . 0.84(3) ?
O2W H2W . 0.85(2) ?
N1 C1 . 1.335(4) ?
N1 C5 . 1.355(4) ?
N1 H1 . 0.878(10) ?
N2 C3 . 1.331(4) ?
N2 H21 . 0.87(2) ?
N2 H22 . 0.88(2) ?
N3 C10 . 1.335(4) ?
N3 C6 . 1.354(4) ?
N3 H3 . 0.88(2) ?
N4 C8 . 1.326(4) ?
N4 H41 . 0.88(2) ?
N4 H42 . 0.88(2) ?
C1 C2 . 1.369(4) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.427(4) ?
C3 C4 . 1.412(4) ?
C4 C5 . 1.347(4) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C7 . 1.354(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.423(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.427(4) ?
C9 C10 . 1.368(4) ?
C10 H10 . 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
N1 H1 O1w 5_667 0.88(2) 1.99(2) 2.820(4) 158(3) y
N2 H22 O2 1_554 0.88(2) 2.01(2) 2.886(3) 172(3) y
N3 H3 O1w 2_664 0.88(2) 2.15(3) 2.871(4) 139(3) y
N4 H42 O4 1_556 0.88(2) 1.99(2) 2.869(3) 173(4) y
O1w H1w O1 . 0.84(2) 1.99(2) 2.826(3) 173(3) y
O2w H2w O3 . 0.85(2) 2.02(2) 2.864(2) 171(3) y
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 . . . . 0.0 ?
N1 C1 C2 C3 . . . . 0.0 ?
N1 C1 C2 S1 . . . . 180.0 ?
O2 S1 C2 C1 . . . . 0.0 ?
O1 S1 C2 C1 . . . . -121.49(11) ?
O1 S1 C2 C1 7_565 . . . 121.49(11) ?
O2 S1 C2 C3 . . . . 180.0 ?
O1 S1 C2 C3 . . . . 58.51(11) ?
O1 S1 C2 C3 7_565 . . . -58.51(11) ?
C1 C2 C3 N2 . . . . 180.0 ?
S1 C2 C3 N2 . . . . 0.0 ?
C1 C2 C3 C4 . . . . 0.0 ?
S1 C2 C3 C4 . . . . 180.0 ?
N2 C3 C4 C5 . . . . 180.0 ?
C2 C3 C4 C5 . . . . 0.0 ?
C3 C4 C5 N1 . . . . 0.0 ?
C1 N1 C5 C4 . . . . 0.0 ?
C10 N3 C6 C7 . . . . 0.0 ?
N3 C6 C7 C8 . . . . 0.0 ?
C6 C7 C8 N4 . . . . 180.0 ?
C6 C7 C8 C9 . . . . 0.0 ?
N4 C8 C9 C10 . . . . 180.0 ?
C7 C8 C9 C10 . . . . 0.0 ?
N4 C8 C9 S2 . . . . 0.0 ?
C7 C8 C9 S2 . . . . 180.0 ?
O4 S2 C9 C10 . . . . 0.0 ?
O3 S2 C9 C10 . . . . 120.95(9) ?
O3 S2 C9 C10 7_565 . . . -120.95(9) ?
O4 S2 C9 C8 . . . . 180.0 ?
O3 S2 C9 C8 . . . . -59.05(9) ?
O3 S2 C9 C8 7_565 . . . 59.05(9) ?
C6 N3 C10 C9 . . . . 0.0 ?
C8 C9 C10 N3 . . . . 0.0 ?
S2 C9 C10 N3 . . . . 180.0 ?
