#------------------------------------------------------------------------------
#$Date: 2020-11-05 10:56:28 +0200 (Thu, 05 Nov 2020) $
#$Revision: 258736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/55/4025532.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_4025532
loop_
_publ_author_name
'Evgeny M. Garanin'
'Yuriy V. Tolmachev'
'Robert R. Hoover'
'Sonya Adas'
'Scott D. Bunge'
'Mahinda Gangoda'
'Anatoly K. Khitrin'
'Stephan M. Woods'
'Andrey Malkovskiy'
'Nulifer Solak'
'Chrys Wesdemiotis'
_publ_contact_author_address
;Kent State University
Chemistry Department
PO Box 5190
Kent, OH 44242
;
_publ_contact_author_email       ytolmach@kent.edu
_publ_contact_author_fax         '330-672-3816 '
_publ_contact_author_name        'Yuriy V. Tolmachev'
_publ_contact_author_phone       330-672-9815
_publ_section_title
;
 Stability and Ring-Shift Tautomerization of Cyclic Anhydrides of
 Benzenehexasulfonic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4860
_journal_page_last               4863
_journal_paper_doi               10.1021/jo1005526
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C6 H13 O21.5 S6'
_chemical_formula_weight         621.52
_chemical_name_common            'C6 O16 S6 (H2O)3.5 (H3O)2'
_chemical_name_systematic
; 
 ? 
;
_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_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                   9.637(3)
_cell_length_b                   42.948(13)
_cell_length_c                   9.514(3)
_cell_measurement_reflns_used    1734
_cell_measurement_temperature    189(2)
_cell_measurement_theta_max      23.40
_cell_measurement_theta_min      3.01
_cell_volume                     3938(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      189(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.1806
_diffrn_reflns_av_sigmaI/netI    0.0852
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29208
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         0.95
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.8685
_exptl_absorpt_correction_T_min  0.8554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.097
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.441
_refine_diff_density_min         -1.219
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.4498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1915
_reflns_number_gt                2277
_reflns_number_total             3544
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1005526_si_002.cif
_cod_data_source_block           monofull
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

2020-10-26
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12 H26 O43 S12'
_cod_original_formula_weight         1243.05
_cod_original_formula_units_Z            4
_cod_database_code               4025532
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O19 O 0.0998(5) 0.00165(11) 0.1508(5) 0.0240(12) Uani 1 1 d D . .
S1 S 0.09851(19) 0.12618(4) -0.2044(2) 0.0212(4) Uani 1 1 d . . .
S2 S 0.26419(19) 0.18817(4) -0.0598(2) 0.0195(4) Uani 1 1 d . . .
S3 S 0.50909(19) 0.16778(4) 0.1805(2) 0.0214(4) Uani 1 1 d . . .
S4 S 0.59012(19) 0.10640(4) 0.22807(19) 0.0216(4) Uani 1 1 d . . .
S5 S 0.45162(18) 0.04486(4) 0.04771(18) 0.0166(4) Uani 1 1 d . . .
S6 S 0.18816(18) 0.06550(4) -0.17072(19) 0.0175(4) Uani 1 1 d . . .
O1 O 0.1390(6) 0.13088(13) -0.3460(5) 0.0329(14) Uani 1 1 d . . .
O2 O -0.0135(5) 0.14222(13) -0.1421(6) 0.0329(14) Uani 1 1 d . . .
O3 O 0.2105(5) 0.18669(12) -0.2017(5) 0.0257(12) Uani 1 1 d . . .
O4 O 0.3937(5) 0.20488(12) -0.0472(5) 0.0271(12) Uani 1 1 d . . .
O5 O 0.1619(5) 0.19612(11) 0.0449(5) 0.0264(12) Uani 1 1 d . . .
O6 O 0.4162(5) 0.18692(12) 0.2571(5) 0.0265(12) Uani 1 1 d . . .
O7 O 0.6256(5) 0.17959(13) 0.1085(6) 0.0326(14) Uani 1 1 d . . .
O8 O 0.5614(5) 0.14129(12) 0.2918(5) 0.0261(12) Uani 1 1 d . . .
O9 O 0.7245(5) 0.10659(12) 0.1671(6) 0.0300(13) Uani 1 1 d . . .
O10 O 0.5528(6) 0.08638(13) 0.3384(5) 0.0303(13) Uani 1 1 d . . .
O11 O 0.5944(5) 0.04769(11) 0.0948(5) 0.0213(11) Uani 1 1 d . . .
O12 O 0.3589(5) 0.03287(12) 0.1554(5) 0.0234(12) Uani 1 1 d . . .
O13 O 0.4352(5) 0.03118(12) -0.0905(5) 0.0260(12) Uani 1 1 d . . .
O14 O 0.1360(5) 0.04028(11) -0.0928(5) 0.0253(12) Uani 1 1 d . . .
O15 O 0.2525(5) 0.06197(12) -0.3031(5) 0.0259(12) Uani 1 1 d . . .
O16 O 0.0577(5) 0.08924(11) -0.1877(5) 0.0225(12) Uani 1 1 d . . .
O17 O 0.3578(5) 0.03478(12) 0.4521(5) 0.0259(12) Uani 1 1 d . . .
O18 O 0.3769(6) 0.20665(13) 0.5788(6) 0.0391(15) Uani 1 1 d . . .
O20 O 0.5338(10) 0.2500 0.6852(15) 0.081(4) Uani 1 2 d S . .
O21 O 0.6187(15) 0.2500 0.9250(15) 0.103(5) Uani 1 2 d S . .
O22 O 0.129(3) 0.2500 0.1935(15) 0.188(12) Uani 1 2 d S . .
O23 O 0.348(2) 0.2500 0.3963(19) 0.157(7) Uani 1 2 d S . .
O24 O 0.405(3) 0.2500 0.133(3) 0.199(10) Uani 1 2 d S . .
C1 C 0.2460(7) 0.12323(15) -0.0892(7) 0.0138(14) Uani 1 1 d . . .
C2 C 0.3116(7) 0.14823(16) -0.0228(7) 0.0149(15) Uani 1 1 d . . .
C3 C 0.4157(7) 0.14034(16) 0.0737(7) 0.0174(15) Uani 1 1 d . . .
C4 C 0.4568(7) 0.10975(16) 0.0958(7) 0.0141(14) Uani 1 1 d . . .
C5 C 0.3963(7) 0.08486(15) 0.0240(7) 0.0130(14) Uani 1 1 d . . .
C6 C 0.2888(7) 0.09262(15) -0.0674(7) 0.0133(14) Uani 1 1 d D . .
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'
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'
H H 0.0000 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 122.7(4) . . ?
O2 S1 O16 104.3(3) . . ?
O1 S1 O16 107.2(3) . . ?
O2 S1 C1 112.5(3) . . ?
O1 S1 C1 111.8(3) . . ?
O16 S1 C1 93.6(3) . . ?
O5 S2 O4 114.5(3) . . ?
O5 S2 O3 114.2(3) . . ?
O4 S2 O3 114.1(3) . . ?
O5 S2 C2 105.2(3) . . ?
O4 S2 C2 103.7(3) . . ?
O3 S2 C2 103.3(3) . . ?
O7 S3 O6 123.0(3) . . ?
O7 S3 O8 108.7(3) . . ?
O6 S3 O8 105.4(3) . . ?
O7 S3 C3 111.1(3) . . ?
O6 S3 C3 110.8(3) . . ?
O8 S3 C3 93.7(3) . . ?
O10 S4 O9 122.9(3) . . ?
O10 S4 O8 103.9(3) . . ?
O9 S4 O8 107.5(3) . . ?
O10 S4 C4 112.8(3) . . ?
O9 S4 C4 111.3(3) . . ?
O8 S4 C4 93.7(3) . . ?
O13 S5 O11 114.7(3) . . ?
O13 S5 O12 115.4(3) . . ?
O11 S5 O12 113.3(3) . . ?
O13 S5 C5 103.8(3) . . ?
O11 S5 C5 103.7(3) . . ?
O12 S5 C5 104.0(3) . . ?
O14 S6 O15 123.0(3) . . ?
O14 S6 O16 105.0(3) . . ?
O15 S6 O16 108.5(3) . . ?
O14 S6 C6 113.7(3) . . ?
O15 S6 C6 108.6(3) . . ?
O16 S6 C6 93.7(3) . . ?
S3 O8 S4 116.7(3) . . ?
S6 O16 S1 115.5(3) . . ?
C6 C1 C2 121.6(6) . . ?
C6 C1 S1 113.0(5) . . ?
C2 C1 S1 125.4(5) . . ?
C1 C2 C3 115.8(6) . . ?
C1 C2 S2 121.7(5) . . ?
C3 C2 S2 122.5(5) . . ?
C4 C3 C2 122.1(6) . . ?
C4 C3 S3 113.1(5) . . ?
C2 C3 S3 124.8(5) . . ?
C3 C4 C5 122.1(6) . . ?
C3 C4 S4 112.6(5) . . ?
C5 C4 S4 125.3(5) . . ?
C6 C5 C4 115.6(6) . . ?
C6 C5 S5 121.5(5) . . ?
C4 C5 S5 122.8(5) . . ?
C1 C6 C5 122.6(6) . . ?
C1 C6 S6 111.6(5) . . ?
C5 C6 S6 125.8(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.411(6) . ?
S1 O1 1.417(6) . ?
S1 O16 1.642(5) . ?
S1 C1 1.799(7) . ?
S2 O5 1.443(5) . ?
S2 O4 1.445(5) . ?
S2 O3 1.447(5) . ?
S2 C2 1.810(7) . ?
S3 O7 1.410(5) . ?
S3 O6 1.417(5) . ?
S3 O8 1.633(5) . ?
S3 C3 1.798(7) . ?
S4 O10 1.404(6) . ?
S4 O9 1.419(5) . ?
S4 O8 1.640(5) . ?
S4 C4 1.804(7) . ?
S5 O13 1.449(5) . ?
S5 O11 1.453(5) . ?
S5 O12 1.453(5) . ?
S5 C5 1.813(7) . ?
S6 O14 1.405(5) . ?
S6 O15 1.412(5) . ?
S6 O16 1.627(5) . ?
S6 C6 1.806(7) . ?
C1 C6 1.393(9) . ?
C1 C2 1.397(9) . ?
C2 C3 1.402(9) . ?
C3 C4 1.388(10) . ?
C4 C5 1.396(9) . ?
C5 C6 1.393(9) . ?
