#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204783.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_2204783
loop_
_publ_author_name
'Bai, Yu'
'Lowary, Todd L.'
'Ferguson, Michael J.'
_publ_section_title
;p-Tolyl
 2,3-anhydro-5,6-O-isopropylidene-1-thio-β-<small>D</small>-gulofuranoside
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2201
_journal_page_last               o2203
_journal_paper_doi               10.1107/S1600536804027266
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H20 O4 S'
_chemical_formula_moiety         'C16 H20 O4 S'
_chemical_formula_sum            'C16 H20 O4 S'
_chemical_formula_weight         308.38
_chemical_melting_point          349
_chemical_name_systematic
;
p-tolyl 2,3-anhydro-5,6-O-isopropylidene-1-thio-β-D-talofuranoside
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1248(7)
_cell_length_b                   12.0366(10)
_cell_length_c                   14.2666(11)
_cell_measurement_reflns_used    5599
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.21
_cell_volume                     1566.9(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997a)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker PLATFORM/SMART 1000 CCD area-detector'
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12110
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.8779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.130
_refine_ls_abs_structure_details 'Flack (1983),  1359 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0327
_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)+(0.0376P)²+0.2041P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                2780
_reflns_number_total             3202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6011.cif
_cod_data_source_block           I
_cod_database_code               2204783
_cod_database_fobs_code          2204783
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'
loop_
_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_type_symbol
S 0.66025(5) 0.04196(5) 0.31980(3) 0.05176(15) Uani d . 1 S
O1 0.46045(13) -0.08484(11) 0.22885(8) 0.0442(3) Uani d . 1 O
O2 0.30951(14) 0.07865(13) 0.15432(9) 0.0540(4) Uani d . 1 O
O5 0.49340(14) -0.16044(12) -0.01461(9) 0.0540(4) Uani d . 1 O
O6 0.26305(13) -0.09677(12) -0.03577(9) 0.0507(3) Uani d . 1 O
C1 0.47463(19) 0.01728(16) 0.27763(13) 0.0438(4) Uani d . 1 C
H1 0.4032 0.0208 0.3307 0.053 Uiso calc R 1 H
C2 0.4400(2) 0.10482(18) 0.20598(13) 0.0483(5) Uani d . 1 C
H2 0.4718 0.1836 0.2151 0.058 Uiso calc R 1 H
C3 0.44962(18) 0.05148(17) 0.11441(13) 0.0434(4) Uani d . 1 C
H3 0.4877 0.0933 0.0590 0.052 Uiso calc R 1 H
C4 0.49636(19) -0.06644(15) 0.13180(12) 0.0400(4) Uani d . 1 C
H4 0.6052 -0.0711 0.1245 0.048 Uiso calc R 1 H
C5 0.4270(2) -0.15966(17) 0.07556(14) 0.0483(5) Uani d . 1 C
H5 0.4451 -0.2323 0.1075 0.058 Uiso calc R 1 H
C6 0.2637(2) -0.1467(2) 0.05546(15) 0.0587(6) Uani d . 1 C
H6A 0.2135 -0.2196 0.0549 0.070 Uiso calc R 1 H
H6B 0.2161 -0.0978 0.1023 0.070 Uiso calc R 1 H
C7 0.38294(19) -0.14459(16) -0.08429(14) 0.0439(4) Uani d . 1 C
C8 0.3410(3) -0.2552(2) -0.12746(17) 0.0682(6) Uani d . 1 C
H8A 0.3068 -0.3057 -0.0782 0.082 Uiso calc R 1 H
H8B 0.4265 -0.2876 -0.1588 0.082 Uiso calc R 1 H
H8C 0.2624 -0.2439 -0.1733 0.082 Uiso calc R 1 H
C9 0.4389(2) -0.0632(2) -0.15481(15) 0.0571(5) Uani d . 1 C
H9A 0.4617 0.0072 -0.1235 0.069 Uiso calc R 1 H
H9B 0.3639 -0.0506 -0.2028 0.069 Uiso calc R 1 H
H9C 0.5277 -0.0928 -0.1843 0.069 Uiso calc R 1 H
C10 0.66366(17) -0.04972(16) 0.41675(12) 0.0417(4) Uani d . 1 C
C11 0.5884(2) -0.02508(18) 0.49798(13) 0.0530(5) Uani d . 1 C
H11 0.5312 0.0408 0.5012 0.064 Uiso calc R 1 H
C12 0.5951(2) -0.0948(2) 0.57448(15) 0.0606(6) Uani d . 1 C
H12 0.5416 -0.0763 0.6294 0.073 Uiso calc R 1 H
C13 0.6773(2) -0.19034(17) 0.57321(16) 0.0550(5) Uani d . 1 C
C14 0.7529(2) -0.21488(18) 0.49205(19) 0.0620(6) Uani d . 1 C
H14 0.8112 -0.2802 0.4896 0.074 Uiso calc R 1 H
C15 0.7459(2) -0.14616(19) 0.41369(16) 0.0570(6) Uani d . 1 C
H15 0.7975 -0.1655 0.3582 0.068 Uiso calc R 1 H
C16 0.6843(3) -0.2655(2) 0.65783(19) 0.0822(8) Uani d . 1 C
H16A 0.7504 -0.3278 0.6449 0.099 Uiso calc R 1 H
H16B 0.5860 -0.2940 0.6717 0.099 Uiso calc R 1 H
H16C 0.7209 -0.2235 0.7118 0.099 Uiso calc R 1 H
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
_geom_angle_publ_flag
C10 S C1 99.95(8) yes
C1 O1 C4 108.52(13) yes
C2 O2 C3 61.02(11) yes
C5 O5 C7 109.14(14) yes
C7 O6 C6 105.68(15) yes
O1 C1 C2 104.76(14) yes
O1 C1 S 112.84(12) yes
C2 C1 S 107.83(13) yes
O1 C1 H1 110.4 ?
C2 C1 H1 110.4 ?
S C1 H1 110.4 ?
O2 C2 C3 59.56(11) yes
O2 C2 C1 111.74(16) yes
C3 C2 C1 106.75(16) yes
O2 C2 H2 121.0 ?
C3 C2 H2 121.0 ?
C1 C2 H2 121.0 ?
O2 C3 C2 59.41(11) yes
O2 C3 C4 113.70(15) yes
C2 C3 C4 106.56(15) yes
O2 C3 H3 120.5 ?
C2 C3 H3 120.5 ?
C4 C3 H3 120.5 ?
O1 C4 C3 103.86(15) yes
O1 C4 C5 107.44(14) yes
C3 C4 C5 119.51(15) yes
O1 C4 H4 108.5 ?
C3 C4 H4 108.5 ?
C5 C4 H4 108.5 ?
O5 C5 C4 107.78(15) yes
O5 C5 C6 104.29(15) yes
C4 C5 C6 115.52(18) yes
O5 C5 H5 109.7 ?
C4 C5 H5 109.7 ?
C6 C5 H5 109.7 ?
O6 C6 C5 102.58(15) yes
O6 C6 H6A 111.3 ?
C5 C6 H6A 111.3 ?
O6 C6 H6B 111.3 ?
C5 C6 H6B 111.3 ?
H6A C6 H6B 109.2 ?
O6 C7 O5 105.02(14) yes
O6 C7 C9 109.05(16) yes
O5 C7 C9 108.36(15) yes
O6 C7 C8 111.11(17) yes
O5 C7 C8 110.09(16) yes
C9 C7 C8 112.88(18) yes
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C7 C9 H9A 109.5 ?
C7 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C7 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C11 C10 C15 118.50(19) ?
C11 C10 S 120.92(15) yes
C15 C10 S 120.55(15) yes
C12 C11 C10 120.80(18) ?
C12 C11 H11 119.6 ?
C10 C11 H11 119.6 ?
C13 C12 C11 121.6(2) ?
C13 C12 H12 119.2 ?
C11 C12 H12 119.2 ?
C12 C13 C14 117.6(2) ?
C12 C13 C16 120.9(2) ?
C14 C13 C16 121.4(2) ?
C13 C14 C15 121.56(19) ?
C13 C14 H14 119.2 ?
C15 C14 H14 119.2 ?
C10 C15 C14 119.9(2) ?
C10 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
C13 C16 H16A 109.5 ?
C13 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C13 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C10 1.7697(19) yes
S C1 1.8217(18) yes
O1 C1 1.419(2) yes
O1 C4 1.440(2) yes
O2 C2 1.435(2) yes
O2 C3 1.437(2) yes
O5 C5 1.422(3) yes
O5 C7 1.428(2) yes
O6 C7 1.417(2) yes
O6 C6 1.433(2) yes
C1 C2 1.502(3) yes
C1 H1 1.0000 ?
C2 C3 1.458(3) yes
C2 H2 1.0000 ?
C3 C4 1.503(3) yes
C3 H3 1.0000 ?
C4 C5 1.518(3) yes
C4 H4 1.0000 ?
C5 C6 1.525(3) yes
C5 H5 1.0000 ?
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 C9 1.494(3) yes
C7 C8 1.517(3) yes
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C8 H8C 0.9800 ?
C9 H9A 0.9800 ?
C9 H9B 0.9800 ?
C9 H9C 0.9800 ?
C10 C11 1.379(3) ?
C10 C15 1.383(3) ?
C11 C12 1.378(3) ?
C11 H11 0.9500 ?
C12 C13 1.373(3) ?
C12 H12 0.9500 ?
C13 C14 1.380(3) ?
C13 C16 1.510(3) ?
C14 C15 1.392(3) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 0.9800 ?
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
C4 O1 C1 C2 29.82(17)
C4 O1 C1 S -87.21(14)
C10 S C1 O1 -75.82(13)
C10 S C1 C2 168.97(13)
C3 O2 C2 C1 -97.22(17)
O1 C1 C2 O2 47.03(18)
S C1 C2 O2 167.45(12)
O1 C1 C2 C3 -16.26(18)
S C1 C2 C3 104.17(15)
C2 O2 C3 C4 95.86(17)
C1 C2 C3 O2 105.77(16)
O2 C2 C3 C4 -108.14(15)
C1 C2 C3 C4 -2.37(19)
C1 O1 C4 C3 -31.17(16)
C1 O1 C4 C5 -158.71(14)
O2 C3 C4 O1 -43.52(18)
C2 C3 C4 O1 19.79(18)
O2 C3 C4 C5 76.1(2)
C2 C3 C4 C5 139.41(17)
C7 O5 C5 C4 -121.00(16)
C7 O5 C5 C6 2.3(2)
O1 C4 C5 O5 -164.23(14)
C3 C4 C5 O5 78.0(2)
O1 C4 C5 C6 79.6(2)
C3 C4 C5 C6 -38.2(2)
C7 O6 C6 C5 35.7(2)
O5 C5 C6 O6 -23.0(2)
C4 C5 C6 O6 95.1(2)
C6 O6 C7 O5 -35.10(19)
C6 O6 C7 C9 -151.05(16)
C6 O6 C7 C8 83.90(19)
C5 O5 C7 O6 19.8(2)
C5 O5 C7 C9 136.19(17)
C5 O5 C7 C8 -99.92(19)
C1 S C10 C11 -73.55(16)
C1 S C10 C15 108.51(16)
C15 C10 C11 C12 0.1(3)
S C10 C11 C12 -177.84(16)
C10 C11 C12 C13 0.5(3)
C11 C12 C13 C14 -0.4(3)
C11 C12 C13 C16 179.6(2)
C12 C13 C14 C15 -0.5(3)
C16 C13 C14 C15 179.5(2)
C11 C10 C15 C14 -1.0(3)
S C10 C15 C14 177.02(15)
C13 C14 C15 C10 1.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13088759
2 PubChem 15946913
