#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/25/8102500.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_8102500
loop_
_publ_author_name
'Wolfgang Frey'
'Sascha Wilhelm Schäfer'
'Jörg Pietruszka'
_publ_section_title
;
 Crystal structure of ethyl
 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside, C16H24O9S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              555
_journal_volume                  224
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H24 O9 S'
_chemical_formula_sum            'C16 H24 O9 S'
_chemical_formula_weight         392.41
_chemical_name_systematic
; 
Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
;
_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                   8.7575(14)
_cell_length_b                   9.128(2)
_cell_length_c                   25.386(5)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      12
_cell_volume                     2029.3(7)
_computing_cell_refinement       'Siemens P3/PC Data Collection System'
_computing_data_collection       'Siemens P3/PC Data Collection System'
_computing_data_reduction        'SHELXTL-plus, XDISK (Sheldrick, 1991)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nicolet P3'
_diffrn_measurement_method       Wyckoff-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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4509
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(14)
_refine_ls_extinction_coef       0.0019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0595
_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)+(0.0328P)²+0.8170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                2722
_reflns_number_total             3991
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2694.cff
_cod_data_source_block           wf1599sp
_cod_original_cell_volume        2029.4(7)
_cod_database_code               8102500
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_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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16247(13) 0.70530(12) 0.20870(4) 0.0649(3) Uani 1 4 a d . . .
O1 O 0.2118(3) 0.6363(3) 0.10953(9) 0.0598(8) Uani 1 4 a d . . .
C1 C 0.3112(5) 0.6267(5) 0.06503(13) 0.0596(10) Uani 1 4 a d . . .
H1 H 0.3691 0.7182 0.0619 0.071 Uiso 1 4 a calc R . .
O2 O 0.3093(3) 0.6178(3) -0.02678(10) 0.0740(9) Uani 1 4 a d . . .
C2 C 0.4220(4) 0.5003(4) 0.07128(13) 0.0542(10) Uani 1 4 a d . . .
H2 H 0.4929 0.4986 0.0414 0.065 Uiso 1 4 a calc R . .
C3 C 0.5109(4) 0.5192(4) 0.12241(12) 0.0480(9) Uani 1 4 a d . . .
H3 H 0.5727 0.6085 0.1204 0.058 Uiso 1 4 a calc R . .
O3 O 0.1081(4) 0.6317(4) -0.08003(11) 0.0747(9) Uani 1 4 a d . . .
O4 O 0.3386(3) 0.3650(3) 0.07325(9) 0.0589(7) Uani 1 4 a d . . .
C4 C 0.4002(4) 0.5313(4) 0.16839(12) 0.0482(9) Uani 1 4 a d . . .
H4 H 0.3419 0.4405 0.1730 0.058 Uiso 1 4 a calc R . .
C5 C 0.2942(4) 0.6617(4) 0.15701(13) 0.0547(10) Uani 1 4 a d . . .
H5 H 0.3589 0.7480 0.1514 0.066 Uiso 1 4 a calc R . .
O5 O 0.5118(5) 0.2536(4) 0.02204(15) 0.1076(13) Uani 1 4 a d . . .
O6 O 0.6087(3) 0.3957(3) 0.13139(9) 0.0568(7) Uani 1 4 a d . . .
C6 C 0.2064(5) 0.6117(6) 0.01766(14) 0.0732(13) Uani 1 4 a d . . .
H6A H 0.1518 0.5193 0.0185 0.088 Uiso 1 4 a calc R . .
H6B H 0.1331 0.6913 0.0164 0.088 Uiso 1 4 a calc R . .
C7 C 0.2430(5) 0.6291(4) -0.07432(15) 0.0573(10) Uani 1 4 a d . . .
O7 O 0.7862(3) 0.5046(4) 0.08114(13) 0.0836(10) Uani 1 4 a d . . .
O8 O 0.4869(3) 0.5658(3) 0.21470(8) 0.0536(6) Uani 1 4 a d . . .
C8 C 0.3604(5) 0.6416(5) -0.11620(15) 0.0785(14) Uani 1 4 a d . . .
H8A H 0.4434 0.5763 -0.1086 0.118 Uiso 1 4 a calc R . .
H8B H 0.3976 0.7404 -0.1176 0.118 Uiso 1 4 a calc R . .
H8C H 0.3160 0.6160 -0.1495 0.118 Uiso 1 4 a calc R . .
O9 O 0.3543(4) 0.4022(3) 0.26259(10) 0.0777(9) Uani 1 4 a d . . .
C9 C 0.3960(6) 0.2468(5) 0.04667(17) 0.0708(13) Uani 1 4 a d . . .
C10 C 0.3007(6) 0.1167(5) 0.05358(18) 0.0829(14) Uani 1 4 a d . . .
H10A H 0.2583 0.1165 0.0884 0.124 Uiso 1 4 a calc R . .
H10B H 0.3617 0.0304 0.0487 0.124 Uiso 1 4 a calc R . .
H10C H 0.2196 0.1178 0.0282 0.124 Uiso 1 4 a calc R . .
C11 C 0.7466(5) 0.4015(6) 0.10685(17) 0.0639(11) Uani 1 4 a d . . .
C12 C 0.8351(6) 0.2643(6) 0.1157(2) 0.1009(17) Uani 1 4 a d . . .
H12A H 0.8210 0.2321 0.1514 0.151 Uiso 1 4 a calc R . .
H12B H 0.9415 0.2827 0.1095 0.151 Uiso 1 4 a calc R . .
H12C H 0.7998 0.1897 0.0920 0.151 Uiso 1 4 a calc R . .
C13 C 0.4444(5) 0.4980(5) 0.26015(14) 0.0550(10) Uani 1 4 a d . . .
C14 C 0.5277(6) 0.5648(5) 0.30560(14) 0.0758(13) Uani 1 4 a d . . .
H14A H 0.5166 0.6694 0.3045 0.114 Uiso 1 4 a calc R . .
H14B H 0.6340 0.5397 0.3035 0.114 Uiso 1 4 a calc R . .
H14C H 0.4860 0.5282 0.3380 0.114 Uiso 1 4 a calc R . .
C15 C 0.0356(5) 0.5487(5) 0.20681(18) 0.0766(12) Uani 1 4 a d . . .
H15A H 0.0058 0.5286 0.1707 0.092 Uiso 1 4 a calc R . .
H15B H 0.0875 0.4630 0.2206 0.092 Uiso 1 4 a calc R . .
C16 C -0.1036(6) 0.5808(7) 0.2394(2) 0.113(2) Uani 1 4 a d . . .
H16A H -0.1726 0.4992 0.2376 0.170 Uiso 1 4 a calc R . .
H16B H -0.1532 0.6670 0.2261 0.170 Uiso 1 4 a calc R . .
H16C H -0.0739 0.5966 0.2754 0.170 Uiso 1 4 a calc R . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C15 101.57(19) . . ?
C5 O1 C1 111.8(3) . . ?
O1 C1 C2 110.7(3) . . ?
O1 C1 C6 105.3(3) . . ?
C2 C1 C6 113.6(4) . . ?
O1 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C6 C1 H1 109.0 . . ?
C7 O2 C6 115.8(3) . . ?
O4 C2 C1 109.4(3) . . ?
O4 C2 C3 109.2(3) . . ?
C1 C2 C3 109.3(3) . . ?
O4 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
O6 C3 C4 108.4(3) . . ?
O6 C3 C2 110.6(3) . . ?
C4 C3 C2 109.7(3) . . ?
O6 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C9 O4 C2 118.3(3) . . ?
O8 C4 C3 107.9(3) . . ?
O8 C4 C5 107.7(3) . . ?
C3 C4 C5 107.2(3) . . ?
O8 C4 H4 111.3 . . ?
C3 C4 H4 111.3 . . ?
C5 C4 H4 111.3 . . ?
O1 C5 C4 109.8(3) . . ?
O1 C5 S1 109.3(2) . . ?
C4 C5 S1 115.0(3) . . ?
O1 C5 H5 107.5 . . ?
C4 C5 H5 107.5 . . ?
S1 C5 H5 107.5 . . ?
C11 O6 C3 115.3(3) . . ?
O2 C6 C1 103.8(3) . . ?
O2 C6 H6A 111.0 . . ?
C1 C6 H6A 111.0 . . ?
O2 C6 H6B 111.0 . . ?
C1 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
O3 C7 O2 122.7(4) . . ?
O3 C7 C8 126.8(4) . . ?
O2 C7 C8 110.5(4) . . ?
C13 O8 C4 116.7(3) . . ?
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 . . ?
O5 C9 O4 122.0(5) . . ?
O5 C9 C10 126.2(5) . . ?
O4 C9 C10 111.8(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 O6 122.5(4) . . ?
O7 C11 C12 126.3(4) . . ?
O6 C11 C12 111.1(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O9 C13 O8 124.4(4) . . ?
O9 C13 C14 126.1(4) . . ?
O8 C13 C14 109.6(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S1 109.2(4) . . ?
C16 C15 H15A 109.8 . . ?
S1 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
S1 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
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 . . ?
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 C5 1.792(4) . ?
S1 C15 1.811(5) . ?
O1 C5 1.424(4) . ?
O1 C1 1.429(4) . ?
C1 C2 1.517(5) . ?
C1 C6 1.519(5) . ?
C1 H1 0.9800 . ?
O2 C7 1.343(5) . ?
O2 C6 1.445(5) . ?
C2 O4 1.435(5) . ?
C2 C3 1.523(5) . ?
C2 H2 0.9800 . ?
C3 O6 1.434(4) . ?
C3 C4 1.521(5) . ?
C3 H3 0.9800 . ?
O3 C7 1.191(4) . ?
O4 C9 1.368(5) . ?
C4 O8 1.435(4) . ?
C4 C5 1.537(5) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
O5 C9 1.193(5) . ?
O6 C11 1.360(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.483(6) . ?
O7 C11 1.197(5) . ?
O8 C13 1.362(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O9 C13 1.179(5) . ?
C9 C10 1.462(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.490(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.495(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.502(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 61.1(4) . . . . ?
C5 O1 C1 C6 -175.7(3) . . . . ?
O1 C1 C2 O4 62.9(4) . . . . ?
C6 C1 C2 O4 -55.4(4) . . . . ?
O1 C1 C2 C3 -56.6(4) . . . . ?
C6 C1 C2 C3 -174.8(3) . . . . ?
O4 C2 C3 O6 56.1(4) . . . . ?
C1 C2 C3 O6 175.8(3) . . . . ?
O4 C2 C3 C4 -63.3(4) . . . . ?
C1 C2 C3 C4 56.3(4) . . . . ?
C1 C2 O4 C9 138.9(3) . . . . ?
C3 C2 O4 C9 -101.5(4) . . . . ?
O6 C3 C4 O8 65.8(4) . . . . ?
C2 C3 C4 O8 -173.4(3) . . . . ?
O6 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 C5 -57.7(4) . . . . ?
C1 O1 C5 C4 -63.4(4) . . . . ?
C1 O1 C5 S1 169.6(3) . . . . ?
O8 C4 C5 O1 176.7(3) . . . . ?
C3 C4 C5 O1 60.8(4) . . . . ?
O8 C4 C5 S1 -59.7(3) . . . . ?
C3 C4 C5 S1 -175.5(3) . . . . ?
C15 S1 C5 O1 55.2(3) . . . . ?
C15 S1 C5 C4 -68.8(3) . . . . ?
C4 C3 O6 C11 -155.4(3) . . . . ?
C2 C3 O6 C11 84.4(4) . . . . ?
C7 O2 C6 C1 -170.3(4) . . . . ?
O1 C1 C6 O2 174.2(3) . . . . ?
C2 C1 C6 O2 -64.5(5) . . . . ?
C6 O2 C7 O3 -1.3(7) . . . . ?
C6 O2 C7 C8 177.3(4) . . . . ?
C3 C4 O8 C13 -140.3(3) . . . . ?
C5 C4 O8 C13 104.3(3) . . . . ?
C2 O4 C9 O5 -0.3(6) . . . . ?
C2 O4 C9 C10 178.5(3) . . . . ?
C3 O6 C11 O7 2.7(6) . . . . ?
C3 O6 C11 C12 -176.2(3) . . . . ?
C4 O8 C13 O9 9.0(6) . . . . ?
C4 O8 C13 C14 -170.4(3) . . . . ?
C5 S1 C15 C16 -167.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8747975
