#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/49/2234902.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_2234902
loop_
_publ_author_name
'Jin, Yu'
_publ_section_title
;
 2-Hydroxypyridinium p-toluenesulfonate
;
_journal_coeditor_code           BH2431
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1669
_journal_paper_doi               10.1107/S1600536812019873
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C5 H6 N O +, C7 H7 O3 S -'
_chemical_formula_moiety         'C5 H6 N O +, C7 H7 O3 S -'
_chemical_formula_sum            'C12 H13 N O4 S'
_chemical_formula_weight         267.29
_chemical_name_systematic
;
2-Hydroxypyridinium p-toluenesulfonate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.293(2)
_cell_length_b                   14.484(3)
_cell_length_c                   15.708(3)
_cell_measurement_reflns_used    3450
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.28
_cell_measurement_theta_min      6.21
_cell_volume                     2341.8(8)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_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  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23178
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.405
_refine_ls_extinction_coef       0.0347(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+1.2062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2239
_reflns_number_total             2688
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2431.cif
_cod_data_source_block           I
_cod_database_code               2234902
_cod_database_fobs_code          2234902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
C C1 0.5889(2) 0.09901(16) 0.81599(13) 0.0461(6) Uani d . 1 1
H H1A 0.6382 0.0453 0.8315 0.069 Uiso calc R 1 1
H H1B 0.4989 0.0890 0.8291 0.069 Uiso calc R 1 1
H H1C 0.6203 0.1514 0.8473 0.069 Uiso calc R 1 1
C C2 0.6034(2) 0.11654(13) 0.72297(12) 0.0322(4) Uani d . 1 1
C C3 0.5108(2) 0.08731(14) 0.66618(13) 0.0356(5) Uani d . 1 1
H H3 0.4365 0.0580 0.6862 0.043 Uiso calc R 1 1
C C4 0.52611(19) 0.10060(14) 0.58087(12) 0.0335(5) Uani d . 1 1
H H4 0.4625 0.0804 0.5431 0.040 Uiso calc R 1 1
C C5 0.63523(18) 0.14370(13) 0.55080(12) 0.0277(4) Uani d . 1 1
C C6 0.72725(19) 0.17508(14) 0.60638(12) 0.0318(4) Uani d . 1 1
H H6 0.8007 0.2055 0.5863 0.038 Uiso calc R 1 1
C C7 0.7102(2) 0.16122(13) 0.69220(13) 0.0342(5) Uani d . 1 1
H H7 0.7728 0.1827 0.7301 0.041 Uiso calc R 1 1
C C8 0.53344(18) 0.14460(13) 0.19333(12) 0.0309(4) Uani d . 1 1
C C9 0.65239(19) 0.10354(14) 0.20266(13) 0.0352(5) Uani d . 1 1
H H9 0.6890 0.0961 0.2564 0.042 Uiso calc R 1 1
C C10 0.7158(2) 0.07393(14) 0.13220(14) 0.0401(5) Uani d . 1 1
H H10 0.7970 0.0464 0.1378 0.048 Uiso calc R 1 1
C C11 0.6624(2) 0.08387(17) 0.05305(14) 0.0446(5) Uani d . 1 1
H H11 0.7052 0.0622 0.0049 0.054 Uiso calc R 1 1
C C12 0.5470(2) 0.12556(16) 0.04656(14) 0.0424(5) Uani d . 1 1
H H12 0.5097 0.1342 -0.0068 0.051 Uiso calc R 1 1
N N1 0.48537(16) 0.15481(12) 0.11587(10) 0.0344(4) Uani d . 1 1
H H1D 0.4112 0.1814 0.1101 0.041 Uiso calc R 1 1
O O1 0.45846(14) 0.17554(12) 0.25338(10) 0.0446(4) Uani d . 1 1
H H1 0.498(3) 0.167(2) 0.303(2) 0.095(12) Uiso d . 1 1
O O2 0.53381(14) 0.17679(12) 0.40618(9) 0.0477(4) Uani d . 1 1
O O3 0.70545(15) 0.06576(10) 0.41196(9) 0.0426(4) Uani d . 1 1
O O4 0.75191(14) 0.22574(10) 0.42828(8) 0.0397(4) Uani d . 1 1
S S1 0.65917(5) 0.15323(3) 0.44102(3) 0.03132(18) Uani d . 1 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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 C3 118.42(18)
C7 C2 C1 120.61(19)
C3 C2 C1 120.97(19)
C4 C3 C2 120.99(19)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 119.90(18)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.00(18)
C6 C5 S1 120.44(15)
C4 C5 S1 119.49(15)
C5 C6 C7 119.34(19)
C5 C6 H6 120.3
C7 C6 H6 120.3
C2 C7 C6 121.31(18)
C2 C7 H7 119.3
C6 C7 H7 119.3
O1 C8 N1 114.05(18)
O1 C8 C9 127.14(19)
N1 C8 C9 118.81(18)
C10 C9 C8 118.75(19)
C10 C9 H9 120.6
C8 C9 H9 120.6
C9 C10 C11 121.1(2)
C9 C10 H10 119.5
C11 C10 H10 119.5
C12 C11 C10 118.3(2)
C12 C11 H11 120.8
C10 C11 H11 120.8
N1 C12 C11 120.4(2)
N1 C12 H12 119.8
C11 C12 H12 119.8
C8 N1 C12 122.64(18)
C8 N1 H1D 118.7
C12 N1 H1D 118.7
C8 O1 H1 109(2)
O3 S1 O4 112.53(9)
O3 S1 O2 112.76(10)
O4 S1 O2 111.68(10)
O3 S1 C5 107.00(9)
O4 S1 C5 106.83(9)
O2 S1 C5 105.48(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.491(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C7 1.364(3)
C2 C3 1.373(3)
C3 C4 1.363(3)
C3 H3 0.9300
C4 C5 1.369(3)
C4 H4 0.9300
C5 C6 1.366(3)
C5 S1 1.7474(19)
C6 C7 1.374(3)
C6 H6 0.9300
C7 H7 0.9300
C8 O1 1.299(2)
C8 N1 1.322(2)
C8 C9 1.369(3)
C9 C10 1.355(3)
C9 H9 0.9300
C10 C11 1.367(3)
C10 H10 0.9300
C11 C12 1.336(3)
C11 H11 0.9300
C12 N1 1.330(3)
C12 H12 0.9300
N1 H1D 0.8600
O1 H1 0.89(4)
O2 S1 1.4425(15)
O3 S1 1.4284(15)
O4 S1 1.4333(16)
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
O1 H1 O2 . 0.89(4) 1.66(4) 2.523(2) 160(3) yes
N1 H1D O4 6_556 0.86 1.86 2.704(2) 166.1 yes
O1 H1 S1 . 0.89(4) 2.73(4) 3.6139(18) 169(3) no
N1 H1D S1 6_556 0.86 2.75 3.4747(18) 143.4 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17344764
