#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223384.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_2223384
loop_
_publ_author_name
'Cai, Ying-Jie'
'Dai, Xi-Bin'
'Liu, Lian'
'Li, Jin'
'Li, Hai-Yan'
_publ_section_title
;
 (4-Hydroxyphenyl)methanaminium 2-(4-sulfanylphenyl)acetate
;
_journal_coeditor_code           HB5068
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2341
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H10 N O +, C8 H7 O2 S -'
_chemical_formula_moiety         'C7 H10 N O +, C8 H7 O2 S -'
_chemical_formula_sum            'C15 H17 N O3 S'
_chemical_formula_weight         291.37
_chemical_name_systematic
;
(4-Hydroxyphenyl)methanaminium 2-(4-sulfanylphenyl)acetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 104.78(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.545(5)
_cell_length_b                   14.792(12)
_cell_length_c                   14.868(11)
_cell_measurement_reflns_used    1267
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.36
_cell_volume                     1391.8(19)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6838
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        'please supply'
_diffrn_standards_interval_count 'please supply'
_diffrn_standards_interval_time  'please supply'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North <i>et al.</i>,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.449
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0537
_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/[\s^2^(Fo^2^)+(0.1018P)^2^+0.3741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1816
_reflns_number_gt                1895
_reflns_number_total             2447
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    hb5068.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S S1 0.76277(18) 0.46123(6) 0.14786(7) 0.0712(4) Uani d D 1
O O1 1.3152(3) 0.89080(12) -0.02444(14) 0.0493(5) Uani d . 1
O O2 1.0949(3) 0.85420(13) 0.06100(13) 0.0495(5) Uani d . 1
C C1 0.9143(5) 0.53974(18) 0.1055(2) 0.0491(7) Uani d . 1
C C2 0.8159(5) 0.59649(19) 0.0354(2) 0.0511(7) Uani d . 1
H H2 0.6711 0.5923 0.0096 0.061 Uiso calc R 1
C C3 0.9338(5) 0.65976(19) 0.0038(2) 0.0482(7) Uani d . 1
H H3A 0.8669 0.6986 -0.0438 0.058 Uiso calc R 1
C C4 1.1530(5) 0.66758(18) 0.04140(18) 0.0425(6) Uani d . 1
C C5 1.2476(5) 0.60815(19) 0.1105(2) 0.0490(7) Uani d . 1
H H5 1.3931 0.6105 0.1354 0.059 Uiso calc R 1
C C6 1.1284(6) 0.54461(19) 0.1435(2) 0.0542(8) Uani d . 1
H H6 1.1935 0.5055 0.1912 0.065 Uiso calc R 1
C C7 1.2790(5) 0.73591(19) 0.0050(2) 0.0501(7) Uani d . 1
H H7A 1.2629 0.7240 -0.0606 0.060 Uiso calc R 1
H H7B 1.4269 0.7273 0.0364 0.060 Uiso calc R 1
C C8 1.2232(4) 0.83435(18) 0.01580(18) 0.0385(6) Uani d . 1
O O3 0.6854(4) 0.88722(13) 0.17658(14) 0.0603(6) Uani d U 1
H H3B 0.7023 0.8765 0.1248 0.090 Uiso d R 1
N N1 0.7229(4) 0.56517(17) 0.46681(18) 0.0451(6) Uani d D 1
C C9 0.6981(5) 0.8088(2) 0.22552(19) 0.051 Uani d U 1
C C10 0.5344(5) 0.7868(2) 0.2620(2) 0.0560(8) Uani d . 1
H H10 0.4183 0.8249 0.2547 0.067 Uiso calc R 1
C C11 0.5448(5) 0.7067(2) 0.3100(2) 0.0494(7) Uani d . 1
H H11 0.4338 0.6897 0.3348 0.059 Uiso calc R 1
C C12 0.7227(4) 0.65084(18) 0.32159(17) 0.0423(6) Uani d . 1
C C13 0.8840(5) 0.6771(2) 0.28458(19) 0.0479(7) Uani d . 1
H H13 1.0024 0.6402 0.2927 0.058 Uiso calc R 1
C C14 0.8762(5) 0.7568(2) 0.23553(19) 0.0525(7) Uani d . 1
H H14 0.9864 0.7744 0.2104 0.063 Uiso calc R 1
C C15 0.7290(6) 0.5601(2) 0.3675(2) 0.0561(8) Uani d . 1
H H15A 0.6097 0.5245 0.3334 0.067 Uiso calc R 1
H H15B 0.8570 0.5290 0.3637 0.067 Uiso calc R 1
H H1B 0.719(5) 0.5117(15) 0.4910(19) 0.054(9) Uiso d D 1
H H1C 0.851(5) 0.585(4) 0.496(3) 0.13(2) Uiso d D 1
H H1A 0.616(4) 0.594(2) 0.473(3) 0.080(13) Uiso d D 1
H H1D 0.719(10) 0.455(4) 0.229(2) 0.18(2) Uiso d 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
S1 0.1102(8) 0.0416(5) 0.0790(6) -0.0173(5) 0.0555(6) -0.0050(4)
O1 0.0561(12) 0.0336(11) 0.0632(12) -0.0046(9) 0.0246(10) -0.0015(9)
O2 0.0546(12) 0.0400(11) 0.0605(12) 0.0055(9) 0.0269(10) -0.0029(9)
C1 0.074(2) 0.0309(15) 0.0500(16) -0.0040(13) 0.0295(15) -0.0075(12)
C2 0.0570(18) 0.0426(17) 0.0537(16) -0.0055(13) 0.0144(14) -0.0068(13)
C3 0.0542(18) 0.0389(16) 0.0494(16) 0.0002(13) 0.0092(13) 0.0027(12)
C4 0.0561(17) 0.0292(14) 0.0457(14) -0.0001(12) 0.0192(12) -0.0055(11)
C5 0.0552(18) 0.0382(15) 0.0513(16) 0.0052(13) 0.0097(13) -0.0038(12)
C6 0.079(2) 0.0376(17) 0.0454(15) 0.0083(15) 0.0148(15) 0.0061(12)
C7 0.0582(18) 0.0348(15) 0.0645(18) 0.0005(13) 0.0290(14) -0.0042(12)
C8 0.0390(14) 0.0337(14) 0.0422(13) -0.0005(11) 0.0094(11) -0.0037(11)
O3 0.0993(17) 0.0344(11) 0.0446(11) 0.0015(11) 0.0138(11) 0.0139(8)
N1 0.0511(15) 0.0340(13) 0.0545(14) -0.0007(12) 0.0211(12) 0.0041(11)
C9 0.071 0.039 0.041 -0.002 0.011 0.000
C10 0.065(2) 0.0479(19) 0.0520(16) 0.0133(15) 0.0091(14) -0.0038(14)
C11 0.0512(17) 0.0486(17) 0.0516(16) -0.0018(14) 0.0192(13) -0.0057(13)
C12 0.0546(16) 0.0352(14) 0.0374(13) -0.0009(12) 0.0124(12) -0.0066(11)
C13 0.0521(17) 0.0464(17) 0.0472(15) 0.0062(13) 0.0163(13) -0.0046(12)
C14 0.0578(18) 0.0570(19) 0.0468(15) -0.0053(15) 0.0208(13) -0.0036(13)
C15 0.082(2) 0.0366(16) 0.0501(16) -0.0017(15) 0.0187(15) -0.0030(12)
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'
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'
N N 0.0061 0.0033 '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
C1 S1 H1D 131(3)
C2 C1 C6 121.0(3)
C2 C1 S1 118.9(3)
C6 C1 S1 120.0(2)
C1 C2 C3 119.0(3)
C1 C2 H2 120.5
C3 C2 H2 120.5
C2 C3 C4 121.8(3)
C2 C3 H3A 119.1
C4 C3 H3A 119.1
C5 C4 C3 117.7(3)
C5 C4 C7 121.3(3)
C3 C4 C7 121.0(3)
C4 C5 C6 120.7(3)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 119.8(3)
C1 C6 H6 120.1
C5 C6 H6 120.1
C4 C7 C8 116.2(2)
C4 C7 H7A 108.2
C8 C7 H7A 108.2
C4 C7 H7B 108.2
C8 C7 H7B 108.2
H7A C7 H7B 107.4
O2 C8 O1 124.8(2)
O2 C8 C7 120.0(2)
O1 C8 C7 115.2(2)
C9 O3 H3B 109.4
C15 N1 H1B 112(2)
C15 N1 H1C 104(4)
H1B N1 H1C 102(4)
C15 N1 H1A 112(3)
H1B N1 H1A 107(3)
H1C N1 H1A 119(5)
C10 C9 O3 118.1(3)
C10 C9 C14 123.9(3)
O3 C9 C14 118.0(3)
C9 C10 C11 118.3(3)
C9 C10 H10 120.9
C11 C10 H10 120.9
C10 C11 C12 120.1(3)
C10 C11 H11 120.0
C12 C11 H11 120.0
C13 C12 C11 119.1(3)
C13 C12 C15 120.2(3)
C11 C12 C15 120.6(3)
C12 C13 C14 121.9(3)
C12 C13 H13 119.1
C14 C13 H13 119.1
C9 C14 C13 116.8(3)
C9 C14 H14 121.6
C13 C14 H14 121.6
N1 C15 C12 113.7(2)
N1 C15 H15A 108.8
C12 C15 H15A 108.8
N1 C15 H15B 108.8
C12 C15 H15B 108.8
H15A C15 H15B 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.746(3)
S1 H1D 1.31(2)
O1 C8 1.266(3)
O2 C8 1.237(3)
C1 C2 1.365(4)
C1 C6 1.373(5)
C2 C3 1.370(4)
C2 H2 0.9300
C3 C4 1.405(4)
C3 H3A 0.9300
C4 C5 1.374(4)
C4 C7 1.491(4)
C5 C6 1.389(4)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.520(4)
C7 H7A 0.9700
C7 H7B 0.9700
O3 C9 1.361(4)
O3 H3B 0.8200
N1 C15 1.490(4)
N1 H1B 0.872(18)
N1 H1C 0.89(2)
N1 H1A 0.845(19)
C9 C10 1.358(5)
C9 C14 1.373(5)
C10 C11 1.376(4)
C10 H10 0.9300
C11 C12 1.402(4)
C11 H11 0.9300
C12 C13 1.366(4)
C12 C15 1.501(4)
C13 C14 1.380(4)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9700
C15 H15B 0.9700
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
N1 H1A O1 4_476 0.845(19) 1.99(2) 2.782(4) 156(4)
N1 H1C O2 4_576 0.89(2) 1.87(2) 2.752(4) 169(5)
N1 H1B O1 2_745 0.872(18) 1.885(19) 2.749(4) 171(3)
O3 H3B N1 4_575 0.82 2.54 3.267(4) 149
C6 H6 O3 2_745 0.93 2.60 3.521(4) 171
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
C6 C1 C2 C3 -0.8(4)
S1 C1 C2 C3 178.3(2)
C1 C2 C3 C4 0.2(4)
C2 C3 C4 C5 1.2(4)
C2 C3 C4 C7 179.0(3)
C3 C4 C5 C6 -1.9(4)
C7 C4 C5 C6 -179.8(3)
C2 C1 C6 C5 0.0(4)
S1 C1 C6 C5 -179.0(2)
C4 C5 C6 C1 1.3(4)
C5 C4 C7 C8 -119.7(3)
C3 C4 C7 C8 62.5(4)
C4 C7 C8 O2 7.1(4)
C4 C7 C8 O1 -172.5(2)
O3 C9 C10 C11 178.8(2)
C14 C9 C10 C11 -1.6(5)
C9 C10 C11 C12 1.0(4)
C10 C11 C12 C13 0.0(4)
C10 C11 C12 C15 -175.3(3)
C11 C12 C13 C14 -0.5(4)
C15 C12 C13 C14 174.8(3)
C10 C9 C14 C13 1.1(4)
O3 C9 C14 C13 -179.3(2)
C12 C13 C14 C9 0.0(4)
C13 C12 C15 N1 120.6(3)
C11 C12 C15 N1 -64.2(4)