#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221670.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_2221670
loop_
_publ_author_name
'Zhang, Chang-Peng'
'Ni, Hao'
'Tu, Hai-Yan'
'Xie, Yong-Rong'
'Yang, Rui-Qing'
_publ_section_title
;
 Genistein-3'-sulfonic acid dihydrate
;
_journal_coeditor_code           FL2244
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1137
_journal_page_last               o1138
_journal_paper_doi               10.1107/S1600536809014767
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H10 O8 S, 2H2 O1'
_chemical_formula_moiety         'C15 H10 O8 S, 2(H2 O1)'
_chemical_formula_sum            'C15 H14 O10 S'
_chemical_formula_weight         386.31
_chemical_name_common
;
Genistein-3'-sulfonic acid dihydrate
;
_chemical_name_systematic
;
5-(5,7-dihydroxy-4-oxo-4H-chromenyl)-2-hydroxybenzenesulfonic acid
dihydrate
;
_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                73.626(3)
_cell_angle_beta                 80.346(3)
_cell_angle_gamma                65.498(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9100(4)
_cell_length_b                   8.1977(3)
_cell_length_c                   14.3431(7)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.81
_cell_volume                     810.61(7)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7136
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.471
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0468
_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)+(0.0499P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                2466
_reflns_number_total             3736
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2244.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_original_cell_volume        810.61(6)
_cod_database_code               2221670
_cod_database_fobs_code          2221670
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 0.91573(8) 0.62831(8) 0.13396(4) 0.02871(17) Uani d . 1 . .
O O1 0.3853(2) 0.9816(2) 0.33901(11) 0.0349(4) Uani d . 1 . .
O O2 0.2966(2) 1.1865(2) 0.46121(12) 0.0463(5) Uani d . 1 . .
H H2A 0.3371 1.1535 0.4101 0.056 Uiso d R 1 . .
O O3 0.0060(2) 0.9940(2) 0.76568(11) 0.0441(5) Uani d . 1 . .
H H3A 0.0326 1.0699 0.7804 0.053 Uiso d R 1 . .
O O4 0.1972(2) 0.62379(19) 0.54241(11) 0.0325(4) Uani d . 1 . .
O O5 0.7199(2) 0.4397(2) 0.05141(12) 0.0483(5) Uani d . 1 . .
H H5A 0.8324 0.4128 0.0492 0.058 Uiso d R 1 . .
C C1 0.3351(3) 0.8670(3) 0.40347(15) 0.0263(5) Uani d . 1 . .
C C2 0.2545(3) 0.9026(3) 0.49667(15) 0.0246(5) Uani d . 1 . .
C C3 0.2355(3) 1.0616(3) 0.52404(16) 0.0296(5) Uani d . 1 . .
C C4 0.1563(3) 1.0929(3) 0.61293(17) 0.0339(6) Uani d . 1 . .
H H4A 0.1465 1.1976 0.6303 0.041 Uiso calc R 1 . .
C C5 0.0900(3) 0.9663(3) 0.67758(16) 0.0305(5) Uani d . 1 . .
C C6 0.1018(3) 0.8113(3) 0.65325(16) 0.0299(5) Uani d . 1 . .
H H6A 0.0550 0.7290 0.6959 0.036 Uiso calc R 1 . .
C C7 0.1848(3) 0.7812(3) 0.56408(16) 0.0263(5) Uani d . 1 . .
C C8 0.2829(3) 0.5863(3) 0.45676(16) 0.0313(5) Uani d . 1 . .
H H8A 0.2944 0.4762 0.4448 0.038 Uiso calc R 1 . .
C C9 0.3528(3) 0.6939(3) 0.38735(15) 0.0261(5) Uani d . 1 . .
C C10 0.4469(3) 0.6336(3) 0.29699(15) 0.0265(5) Uani d . 1 . .
C C11 0.3792(3) 0.5469(3) 0.25092(17) 0.0352(6) Uani d . 1 . .
H H11A 0.2693 0.5304 0.2753 0.042 Uiso calc R 1 . .
C C12 0.4730(3) 0.4846(3) 0.16923(18) 0.0392(6) Uani d . 1 . .
H H12A 0.4249 0.4277 0.1391 0.047 Uiso calc R 1 . .
C C13 0.6385(3) 0.5062(3) 0.13165(16) 0.0317(5) Uani d . 1 . .
C C14 0.7058(3) 0.5965(3) 0.17563(15) 0.0250(5) Uani d . 1 . .
C C15 0.6094(3) 0.6585(3) 0.25784(15) 0.0259(5) Uani d . 1 . .
H H15A 0.6554 0.7181 0.2872 0.031 Uiso calc R 1 . .
O O1W 0.6658(3) 0.1139(2) 0.02597(15) 0.0646(6) Uani d . 1 . .
H H3 0.7677 0.0288 0.0470 0.078 Uiso d R 1 . .
H H4 0.6800 0.2140 0.0191 0.078 Uiso d R 1 . .
O O2W 0.3261(3) 0.0875(3) 0.13170(15) 0.0775(7) Uani d . 1 . .
H H1 0.4261 0.0988 0.1045 0.093 Uiso d R 1 . .
H H2 0.2363 0.1863 0.1398 0.093 Uiso d R 1 . .
O O6A 0.9142(16) 0.6736(12) 0.0261(8) 0.0346(14) Uani d P 0.54 . .
O O7A 1.067(2) 0.456(2) 0.1681(9) 0.043(2) Uani d P 0.54 . .
O O8A 0.8999(11) 0.7821(10) 0.1651(4) 0.0369(13) Uani d P 0.54 . .
O O6B 0.899(2) 0.7323(15) 0.0381(10) 0.067(3) Uani d P 0.46 . .
O O7B 1.059(2) 0.450(3) 0.1480(12) 0.069(5) Uani d P 0.46 . .
O O8B 0.9427(13) 0.7255(13) 0.2012(5) 0.061(3) Uani d P 0.46 . .
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'
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
O8A S1 O7A . . 117.5(7) ?
O8A S1 O6A . . 110.1(4) ?
O7A S1 O6A . . 110.5(6) ?
O8A S1 C14 . . 105.6(3) ?
O7A S1 C14 . . 107.8(7) ?
O6A S1 C14 . . 104.3(5) ?
O6B S1 O7B . . 115.3(8) ?
O6B S1 O8B . . 112.3(5) ?
O7B S1 O8B . . 107.7(8) ?
O6B S1 C14 . . 108.5(6) ?
O8A S1 C14 . . 105.6(3) ?
O7B S1 C14 . . 106.3(9) ?
O7A S1 C14 . . 107.8(7) ?
O6A S1 C14 . . 104.3(5) ?
O8B S1 C14 . . 106.2(4) ?
C3 O2 H2A . . 109.4 ?
C5 O3 H3A . . 109.5 ?
C8 O4 C7 . . 118.66(16) ?
C13 O5 H5A . . 109.4 ?
O1 C1 C2 . . 121.64(19) ?
O1 C1 C9 . . 122.13(19) ?
C2 C1 C9 . . 116.23(18) ?
C7 C2 C3 . . 116.69(19) ?
C7 C2 C1 . . 120.75(19) ?
C3 C2 C1 . . 122.53(19) ?
O2 C3 C4 . . 119.2(2) ?
O2 C3 C2 . . 119.6(2) ?
C4 C3 C2 . . 121.2(2) ?
C3 C4 C5 . . 119.6(2) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
O3 C5 C6 . . 117.1(2) ?
O3 C5 C4 . . 121.6(2) ?
C6 C5 C4 . . 121.3(2) ?
C5 C6 C7 . . 118.1(2) ?
C5 C6 H6A . . 121.0 ?
C7 C6 H6A . . 121.0 ?
O4 C7 C6 . . 116.80(19) ?
O4 C7 C2 . . 120.09(19) ?
C6 C7 C2 . . 123.1(2) ?
C9 C8 O4 . . 125.7(2) ?
C9 C8 H8A . . 117.2 ?
O4 C8 H8A . . 117.2 ?
C8 C9 C1 . . 118.4(2) ?
C8 C9 C10 . . 119.97(19) ?
C1 C9 C10 . . 121.67(18) ?
C15 C10 C11 . . 118.0(2) ?
C15 C10 C9 . . 120.2(2) ?
C11 C10 C9 . . 121.7(2) ?
C12 C11 C10 . . 120.9(2) ?
C12 C11 H11A . . 119.5 ?
C10 C11 H11A . . 119.5 ?
C11 C12 C13 . . 120.7(2) ?
C11 C12 H12A . . 119.6 ?
C13 C12 H12A . . 119.6 ?
O5 C13 C14 . . 124.9(2) ?
O5 C13 C12 . . 116.1(2) ?
C14 C13 C12 . . 119.0(2) ?
C13 C14 C15 . . 119.4(2) ?
C13 C14 S1 . . 122.28(16) ?
C15 C14 S1 . . 118.27(17) ?
C10 C15 C14 . . 121.9(2) ?
C10 C15 H15A . . 119.1 ?
C14 C15 H15A . . 119.1 ?
H3 O1W H4 . . 105.1 ?
H1 O2W H2 . . 116.1 ?
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 O6B . 1.394(14) ?
S1 O8A . 1.404(7) ?
S1 O7B . 1.412(16) ?
S1 O7A . 1.438(14) ?
S1 O6A . 1.487(11) ?
S1 O8B . 1.501(8) ?
S1 C14 . 1.766(2) ?
O1 C1 . 1.262(2) ?
O2 C3 . 1.356(3) ?
O2 H2A . 0.8207 ?
O3 C5 . 1.358(2) ?
O3 H3A . 0.8205 ?
O4 C8 . 1.350(2) ?
O4 C7 . 1.372(2) ?
O5 C13 . 1.360(2) ?
O5 H5A . 0.8206 ?
C1 C2 . 1.435(3) ?
C1 C9 . 1.447(3) ?
C2 C7 . 1.401(3) ?
C2 C3 . 1.408(3) ?
C3 C4 . 1.366(3) ?
C4 C5 . 1.399(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.374(3) ?
C6 C7 . 1.375(3) ?
C6 H6A . 0.9300 ?
C8 C9 . 1.342(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.487(3) ?
C10 C15 . 1.385(3) ?
C10 C11 . 1.389(3) ?
C11 C12 . 1.384(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.392(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.390(3) ?
C14 C15 . 1.395(3) ?
C15 H15A . 0.9300 ?
O1W H3 . 0.8508 ?
O1W H4 . 0.8502 ?
O2W H1 . 0.8500 ?
O2W H2 . 0.8500 ?
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
O2W H1 O1W 1_555 0.85 2.07 2.915(3) 173
O2W H2 O7A 1_455 0.85 2.17 2.999(15) 165
O2W H2 O6A 2_665 0.85 2.58 2.903(13) 104
O2 H2A O1 1_555 0.82 1.85 2.580(2) 148
O1W H3 O8A 1_545 0.85 2.23 2.968(7) 146
O3 H3A O8A 2_676 0.82 1.89 2.705(8) 171
O1W H4 O5 1_555 0.85 2.18 3.000(2) 162
O5 H5A O6A 1_555 0.82 2.40 2.835(12) 114
O5 H5A O6A 2_765 0.82 2.05 2.784(14) 148
C6 H6A O7A 2_666 0.93 2.44 3.356(15) 169
C8 H8A O2 1_545 0.93 2.31 3.217(3) 164
C15 H15A O1 1_555 0.93 2.52 2.944(3) 108
C15 H15A O8A 1_555 0.93 2.50 2.868(9) 104
