#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017193.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_2017193
loop_
_publ_author_name
'Manoj, K.'
'Gonnade, R. G.'
'Bhadbhade, M. M.'
'Shashidhar, M. S.'
_publ_section_title
;
 Dipolar S=O···C=O and
 C---H···O interactions in the molecular
 organization of
 4,6-di-O-acetyl-2-O-tosyl-myo-inositol
 1,3,5-orthoesters
;
_journal_coeditor_code           SF3106
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o335
_journal_page_last               o338
_journal_paper_doi               10.1107/S0108270109017211
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H20 O10 S'
_chemical_formula_moiety         'C18 H20 O10 S'
_chemical_formula_sum            'C18 H20 O10 S'
_chemical_formula_weight         428.40
_chemical_name_systematic
;
4,6-di-O-acetyl-2-O-tosyl-myo-inositol
1,3,5-orthoformate
;
_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                100.4260(10)
_cell_angle_beta                 103.1230(10)
_cell_angle_gamma                99.6600(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5756(6)
_cell_length_b                   11.0381(8)
_cell_length_c                   11.2005(8)
_cell_measurement_reflns_used    4544
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.38
_cell_volume                     991.04(12)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF
(Westrip, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker SMART APEX'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω and φ Scan'
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9864
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_correction_T_min  0.9010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.3245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                3179
_reflns_number_total             3581
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3106.cif
_cod_data_source_block           I
_cod_database_code               2017193
_cod_database_fobs_code          2017193
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 1.13187(6) 0.28646(5) 0.50072(5) 0.05192(17) Uani d . 1 . .
O O1 0.97168(16) 0.11776(13) 0.08998(14) 0.0576(4) Uani d . 1 A .
O O2 1.06658(15) 0.20864(12) 0.35854(12) 0.0506(3) Uani d . 1 . .
O O3 0.79359(16) 0.01944(12) 0.18764(13) 0.0532(3) Uani d . 1 A .
O O4 0.60749(14) 0.28741(13) 0.24659(12) 0.0510(3) Uani d . 1 . .
O O5 0.69156(16) 0.06411(13) -0.00552(12) 0.0546(4) Uani d . 1 A .
O O6 0.82034(19) 0.40686(13) 0.11872(13) 0.0607(4) Uani d D 1 . .
O O7 1.27275(18) 0.24053(16) 0.54906(16) 0.0727(5) Uani d . 1 . .
O O8 1.14713(18) 0.41723(13) 0.50277(15) 0.0644(4) Uani d . 1 . .
O O9 0.34999(18) 0.25258(16) 0.13177(17) 0.0786(5) Uani d . 1 . .
C C1 0.9644(2) 0.24132(18) 0.15071(18) 0.0493(4) Uani d . 1 . .
H H1 1.0686 0.3005 0.1629 0.059 Uiso calc R 1 A .
C C2 0.9272(2) 0.23932(17) 0.27681(16) 0.0425(4) Uani d . 1 A .
H H2 0.9097 0.3216 0.3145 0.051 Uiso calc R 1 . .
C C3 0.7741(2) 0.13669(17) 0.25463(17) 0.0446(4) Uani d . 1 . .
H H3 0.7535 0.1274 0.3354 0.054 Uiso calc R 1 A .
C C4 0.6280(2) 0.17260(17) 0.17381(17) 0.0448(4) Uani d . 1 A .
H H4 0.5294 0.1061 0.1575 0.054 Uiso calc R 1 . .
C C5 0.6666(2) 0.18537(18) 0.04987(17) 0.0481(4) Uani d . 1 . .
H H5 0.5744 0.2066 -0.0058 0.058 Uiso calc R 1 A .
C C6 0.8256(2) 0.27979(18) 0.06432(18) 0.0511(5) Uani d . 1 A .
H H6 0.8471 0.2764 -0.0184 0.061 Uiso calc R 1 . .
C C7 0.8237(2) 0.03049(19) 0.0718(2) 0.0551(5) Uani d . 1 . .
H H7 0.8347 -0.0521 0.0291 0.066 Uiso calc R 1 A .
C C8 0.9742(2) 0.23742(17) 0.56804(17) 0.0471(4) Uani d . 1 . .
C C9 0.8484(3) 0.30170(18) 0.56673(19) 0.0545(5) Uani d . 1 . .
H H9 0.8536 0.3763 0.5389 0.065 Uiso calc R 1 . .
C C10 0.7159(3) 0.2540(2) 0.6070(2) 0.0608(5) Uani d . 1 . .
H H10 0.6308 0.2966 0.6051 0.073 Uiso calc R 1 . .
C C11 0.7066(3) 0.1438(2) 0.65035(19) 0.0598(5) Uani d . 1 . .
C C12 0.8367(3) 0.0842(2) 0.6551(2) 0.0657(6) Uani d . 1 . .
H H12 0.8340 0.0119 0.6869 0.079 Uiso calc R 1 . .
C C13 0.9696(3) 0.12861(19) 0.6141(2) 0.0585(5) Uani d . 1 . .
H H13 1.0552 0.0865 0.6171 0.070 Uiso calc R 1 . .
C C14 0.5575(4) 0.0897(3) 0.6879(3) 0.0916(9) Uani d . 1 . .
H H14A 0.4776 0.0355 0.6153 0.137 Uiso calc R 1 . .
H H14B 0.5116 0.1570 0.7228 0.137 Uiso calc R 1 . .
H H14C 0.5876 0.0419 0.7498 0.137 Uiso calc R 1 . .
C C15 0.4592(2) 0.31450(19) 0.21942(19) 0.0505(5) Uani d . 1 . .
C C16 0.4525(3) 0.4309(2) 0.3063(2) 0.0685(6) Uani d . 1 . .
H H16A 0.3805 0.4753 0.2615 0.103 Uiso calc R 1 . .
H H16B 0.5605 0.4840 0.3390 0.103 Uiso calc R 1 . .
H H16C 0.4122 0.4089 0.3745 0.103 Uiso calc R 1 . .
O O10 0.6925(14) 0.4293(5) -0.0650(5) 0.122(3) Uani d PDU 0.581(15) A 1
C C17 0.7656(7) 0.4774(8) 0.0455(5) 0.098(3) Uani d PDU 0.581(15) A 1
C C18 0.8025(17) 0.6142(10) 0.1121(10) 0.093(3) Uani d PDU 0.581(15) A 1
H H18A 0.7772 0.6642 0.0515 0.140 Uiso calc PR 0.581(15) A 1
H H18B 0.9167 0.6406 0.1564 0.140 Uiso calc PR 0.581(15) A 1
H H18C 0.7373 0.6251 0.1708 0.140 Uiso calc PR 0.581(15) A 1
O O10' 0.818(2) 0.4636(8) -0.0634(8) 0.120(3) Uani d PDU 0.419(15) A 2
C C17' 0.8016(10) 0.4872(12) 0.0435(6) 0.094(3) Uani d PDU 0.419(15) A 2
C C18' 0.760(3) 0.6030(17) 0.1115(17) 0.110(5) Uani d PDU 0.419(15) A 2
H H18D 0.6430 0.5927 0.0927 0.165 Uiso calc PR 0.419(15) A 2
H H18E 0.8060 0.6755 0.0845 0.165 Uiso calc PR 0.419(15) A 2
H H18F 0.8045 0.6148 0.2006 0.165 Uiso calc PR 0.419(15) A 2
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
O7 S1 O8 . . 119.80(9) ?
O7 S1 O2 . . 103.66(9) ?
O8 S1 O2 . . 108.71(8) ?
O7 S1 C8 . . 110.63(10) ?
O8 S1 C8 . . 109.05(9) ?
O2 S1 C8 . . 103.66(8) ?
C7 O1 C1 . . 111.31(13) ?
C2 O2 S1 . . 118.36(11) ?
C7 O3 C3 . . 110.97(14) ?
C15 O4 C4 . . 117.37(13) ?
C7 O5 C5 . . 111.85(13) ?
C17' O6 C6 . . 118.4(4) ?
C17 O6 C6 . . 119.2(3) ?
O1 C1 C2 . . 110.12(16) ?
O1 C1 C6 . . 106.78(15) ?
C2 C1 C6 . . 109.61(15) ?
O1 C1 H1 . . 110.1 ?
C2 C1 H1 . . 110.1 ?
C6 C1 H1 . . 110.1 ?
O2 C2 C1 . . 107.81(14) ?
O2 C2 C3 . . 109.64(14) ?
C1 C2 C3 . . 108.09(15) ?
O2 C2 H2 . . 110.4 ?
C1 C2 H2 . . 110.4 ?
C3 C2 H2 . . 110.4 ?
O3 C3 C2 . . 110.26(14) ?
O3 C3 C4 . . 107.71(14) ?
C2 C3 C4 . . 109.14(15) ?
O3 C3 H3 . . 109.9 ?
C2 C3 H3 . . 109.9 ?
C4 C3 H3 . . 109.9 ?
O4 C4 C5 . . 114.16(16) ?
O4 C4 C3 . . 106.09(13) ?
C5 C4 C3 . . 107.57(14) ?
O4 C4 H4 . . 109.6 ?
C5 C4 H4 . . 109.6 ?
C3 C4 H4 . . 109.6 ?
O5 C5 C4 . . 106.03(15) ?
O5 C5 C6 . . 105.65(14) ?
C4 C5 C6 . . 114.32(15) ?
O5 C5 H5 . . 110.2 ?
C4 C5 H5 . . 110.2 ?
C6 C5 H5 . . 110.2 ?
O6 C6 C1 . . 108.51(15) ?
O6 C6 C5 . . 112.60(16) ?
C1 C6 C5 . . 107.81(16) ?
O6 C6 H6 . . 109.3 ?
C1 C6 H6 . . 109.3 ?
C5 C6 H6 . . 109.3 ?
O3 C7 O1 . . 110.69(16) ?
O3 C7 O5 . . 111.00(15) ?
O1 C7 O5 . . 111.09(17) ?
O3 C7 H7 . . 108.0 ?
O1 C7 H7 . . 108.0 ?
O5 C7 H7 . . 108.0 ?
C9 C8 C13 . . 120.4(2) ?
C9 C8 S1 . . 119.92(15) ?
C13 C8 S1 . . 119.52(16) ?
C10 C9 C8 . . 119.34(18) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C9 C10 C11 . . 121.3(2) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C11 C10 . . 118.1(2) ?
C12 C11 C14 . . 121.3(2) ?
C10 C11 C14 . . 120.6(2) ?
C13 C12 C11 . . 121.89(19) ?
C13 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
C12 C13 C8 . . 118.91(19) ?
C12 C13 H13 . . 120.5 ?
C8 C13 H13 . . 120.5 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O9 C15 O4 . . 122.26(18) ?
O9 C15 C16 . . 125.96(18) ?
O4 C15 C16 . . 111.72(16) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O10 C17 O6 . . 119.5(7) ?
O10 C17 C18 . . 127.8(5) ?
O6 C17 C18 . . 112.7(6) ?
O10' C17' O6 . . 122.0(10) ?
O10' C17' C18' . . 128.6(8) ?
O6 C17' C18' . . 109.4(10) ?
C17' C18' H18D . . 109.5 ?
C17' C18' H18E . . 109.5 ?
H18D C18' H18E . . 109.5 ?
C17' C18' H18F . . 109.5 ?
H18D C18' H18F . . 109.5 ?
H18E C18' H18F . . 109.5 ?
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 O7 . 1.4204(14) ?
S1 O8 . 1.4228(15) ?
S1 O2 . 1.5894(14) ?
S1 C8 . 1.748(2) ?
O1 C7 . 1.408(2) ?
O1 C1 . 1.428(2) ?
O2 C2 . 1.4602(19) ?
O3 C7 . 1.401(3) ?
O3 C3 . 1.430(2) ?
O4 C15 . 1.336(2) ?
O4 C4 . 1.438(2) ?
O5 C7 . 1.408(2) ?
O5 C5 . 1.442(2) ?
O6 C17' . 1.334(12) ?
O6 C17 . 1.295(8) ?
O6 C6 . 1.437(2) ?
O9 C15 . 1.197(2) ?
C1 C2 . 1.520(3) ?
C1 C6 . 1.526(3) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.523(2) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.526(2) ?
C3 H3 . 0.9800 ?
C4 C5 . 1.523(3) ?
C4 H4 . 0.9800 ?
C5 C6 . 1.527(3) ?
C5 H5 . 0.9800 ?
C6 H6 . 0.9800 ?
C7 H7 . 0.9800 ?
C8 C9 . 1.386(3) ?
C8 C13 . 1.388(3) ?
C9 C10 . 1.375(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.386(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.383(3) ?
C11 C14 . 1.500(3) ?
C12 C13 . 1.372(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C16 . 1.483(3) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
O10 C17 . 1.226(4) ?
C17 C18 . 1.504(6) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
O10' C17' . 1.222(5) ?
C17' C18' . 1.506(6) ?
C18' H18D . 0.9600 ?
C18' H18E . 0.9600 ?
C18' H18F . 0.9600 ?
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
C1 H1 O9 1_655 0.98 2.64 3.344(2) 129.0
C4 H4 O5 2_655 0.98 2.49 3.370(2) 149.3
C7 H7 O1 2_755 0.98 2.47 3.221(2) 132.8
C7 H7 O9 2_655 0.98 2.60 3.391(2) 138.3
C9 H9 O8 2_766 0.93 2.41 3.329(2) 170.5
C14 H14C O5 1_556 0.96 2.63 3.443(3) 142.2
C16 H16B O8 2_766 0.96 2.64 3.551(3) 158.1
C16 H16A O10 2_665 0.96 2.60 3.444(5) 146.2
C18 H18A O9 2_665 0.96 2.50 3.437(15) 165.2
