##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     CRYSTALS_ver_12.86
_chemical_name_systematic
;
4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
;
_chemical_formula_moiety     'C21 H26 O10 S1'
_chemical_formula_sum     'C21 H26 O10 S1'
_chemical_formula_iupac     'C21 H26 O10 S1'
_chemical_formula_weight     470.50
_chemical_melting_point     'not measured'
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     8.6218(2)
_cell_length_b     15.2945(3)
_cell_length_c     17.5449(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2313.58(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     18167
_cell_measurement_theta_min     5
_cell_measurement_theta_max     28
_cell_measurement_temperature     150
_exptl_crystal_description     fragment
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.44
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.351
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     992
_exptl_absorpt_coefficient_mu     0.193
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.94
_exptl_absorpt_correction_T_max     0.96
_diffrn_ambient_temperature     150
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Area'
_diffrn_measurement_device     'Bruker--Nonius KappaCCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     18167
_diffrn_reflns_av_R_equivalents     0.033
_diffrn_reflns_theta_min     5.195
_diffrn_reflns_theta_max     27.482
_diffrn_reflns_theta_full     27.482
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
_refine_special_details
;
The hydrogen atoms were all located in a difference map, but those attached to
carbon atoms were repositioned geometrically. The H atoms were initially
refined with soft restraints on the bond lengths and angles to regularize
their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89,
N---H to 0.86, O---H = 0.82 Å) and Uiso(H) (in the range 1.2--1.5
times Ueq of the parent atom), after which the positions were refined
with riding constraints.
;
_reflns_number_total     5253
_reflns_number_gt     4562
_reflns_threshold_expression     I>2.0σ(I)
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0443
_refine_ls_R_factor_gt     0.0356
_refine_ls_wR_factor_all     0.0466
_refine_ls_wR_factor_gt     0.0362
_refine_ls_wR_factor_ref     0.0345
_refine_ls_goodness_of_fit_ref     1.0656
_refine_ls_number_reflns     4305
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
 Method = Robust Weighting (Prince, 1982)
 W = [weight] * [1-(deltaF/6*sigmaF)²]²
 Ai are:
 0.350 0.808E-01 0.749E-01
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000996
_refine_diff_density_max     0.27
_refine_diff_density_min     -0.26
_refine_ls_extinction_method     'None'
_refine_ls_abs_structure_details     'Flack (1983), 2269 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.06(6)
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
    'S   ' 0.1246 0.1234 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection     'COLLECT (Nonius, 2001).'
_computing_cell_refinement     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction
;DENZO/SCALEPACK (Otwinowski & Minor, 1997) and
Hooft et al. (2008
;
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al.,  2003)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'CRYSTALS (Betteridge et al.,  2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.42086(19) 0.44662(10) 0.48435(10) 0.0278 Uani 1.0000 . .
    C C2 0.4623(2) 0.51157(10) 0.54678(9) 0.0290 Uani 1.0000 . .
    C C3 0.3411(2) 0.51009(11) 0.60972(9) 0.0293 Uani 1.0000 . .
    C C4 0.1802(2) 0.52268(11) 0.57752(9) 0.0272 Uani 1.0000 . .
    C C5 0.15111(19) 0.45186(11) 0.51798(10) 0.0276 Uani 1.0000 . .
    C C6 -0.0057(2) 0.45811(11) 0.48018(11) 0.0333 Uani 1.0000 . .
    O O1 0.26620(14) 0.45701(8) 0.45874(7) 0.0279 Uani 1.0000 . .
    S S1 0.46552(6) 0.33607(3) 0.51937(3) 0.0339 Uani 1.0000 . .
    C C7 0.4854(2) 0.27972(11) 0.43134(10) 0.0306 Uani 1.0000 . .
    C C8 0.3607(2) 0.23433(13) 0.40015(12) 0.0390 Uani 1.0000 . .
    C C9 0.3778(2) 0.19047(13) 0.33162(13) 0.0415 Uani 1.0000 . .
    C C10 0.5189(2) 0.19112(11) 0.29336(10) 0.0336 Uani 1.0000 . .
    C C11 0.6441(2) 0.23463(12) 0.32488(10) 0.0329 Uani 1.0000 . .
    C C12 0.6267(2) 0.27925(12) 0.39370(11) 0.0317 Uani 1.0000 . .
    O O2 0.52304(19) 0.14679(9) 0.22609(8) 0.0434 Uani 1.0000 . .
    C C13 0.6652(3) 0.14715(16) 0.18392(12) 0.0527 Uani 1.0000 . .
    O O3 0.46128(15) 0.59743(7) 0.51222(7) 0.0317 Uani 1.0000 . .
    C C14 0.5794(2) 0.65171(13) 0.52960(12) 0.0401 Uani 1.0000 . .
    O O4 0.6831(2) 0.63201(11) 0.57186(12) 0.0741 Uani 1.0000 . .
    C C15 0.5639(3) 0.73699(13) 0.48905(13) 0.0471 Uani 1.0000 . .
    O O5 0.36891(17) 0.58054(9) 0.66273(7) 0.0383 Uani 1.0000 . .
    C C16 0.4478(3) 0.56208(15) 0.72635(11) 0.0448 Uani 1.0000 . .
    O O6 0.5010(3) 0.49096(12) 0.73892(11) 0.0767 Uani 1.0000 . .
    C C17 0.4616(4) 0.6411(2) 0.77608(14) 0.0696 Uani 1.0000 . .
    O O7 0.06770(15) 0.50827(8) 0.63709(7) 0.0334 Uani 1.0000 . .
    C C18 0.0046(2) 0.58014(12) 0.67193(10) 0.0374 Uani 1.0000 . .
    O O8 0.04098(19) 0.65349(8) 0.65627(8) 0.0466 Uani 1.0000 . .
    C C19 -0.1121(3) 0.55302(15) 0.72963(15) 0.0595 Uani 1.0000 . .
    O O9 -0.01388(15) 0.54017(8) 0.43982(7) 0.0341 Uani 1.0000 . .
    C C20 -0.1484(2) 0.55419(14) 0.40247(11) 0.0378 Uani 1.0000 . .
    O O10 -0.25415(18) 0.50261(13) 0.40449(10) 0.0578 Uani 1.0000 . .
    C C21 -0.1459(3) 0.63787(15) 0.35898(12) 0.0476 Uani 1.0000 . .
    H H11 0.4895 0.4569 0.4405 0.0329 Uiso 1.0000 . .
    H H21 0.5668 0.4991 0.5672 0.0352 Uiso 1.0000 . .
    H H31 0.3454 0.4533 0.6367 0.0357 Uiso 1.0000 . .
    H H41 0.1694 0.5812 0.5567 0.0321 Uiso 1.0000 . .
    H H51 0.1563 0.3935 0.5428 0.0332 Uiso 1.0000 . .
    H H61 -0.0883 0.4553 0.5182 0.0412 Uiso 1.0000 . .
    H H62 -0.0189 0.4084 0.4439 0.0426 Uiso 1.0000 . .
    H H81 0.2625 0.2331 0.4264 0.0476 Uiso 1.0000 . .
    H H91 0.2901 0.1590 0.3105 0.0504 Uiso 1.0000 . .
    H H111 0.7447 0.2344 0.2983 0.0390 Uiso 1.0000 . .
    H H121 0.7146 0.3117 0.4155 0.0391 Uiso 1.0000 . .
    H H131 0.6468 0.1130 0.1371 0.0801 Uiso 1.0000 . .
    H H132 0.7494 0.1231 0.2157 0.0787 Uiso 1.0000 . .
    H H133 0.6895 0.2084 0.1693 0.0802 Uiso 1.0000 . .
    H H152 0.6314 0.7806 0.5124 0.0710 Uiso 1.0000 . .
    H H151 0.4574 0.7570 0.4924 0.0705 Uiso 1.0000 . .
    H H153 0.5884 0.7284 0.4351 0.0710 Uiso 1.0000 . .
    H H172 0.5416 0.6301 0.8131 0.1035 Uiso 1.0000 . .
    H H171 0.3633 0.6515 0.7991 0.1058 Uiso 1.0000 . .
    H H173 0.4931 0.6909 0.7446 0.1044 Uiso 1.0000 . .
    H H192 -0.1471 0.6041 0.7564 0.0883 Uiso 1.0000 . .
    H H191 -0.0655 0.5113 0.7647 0.0876 Uiso 1.0000 . .
    H H193 -0.2004 0.5241 0.7047 0.0882 Uiso 1.0000 . .
    H H212 -0.2487 0.6498 0.3385 0.0716 Uiso 1.0000 . .
    H H211 -0.1161 0.6835 0.3930 0.0723 Uiso 1.0000 . .
    H H213 -0.0724 0.6340 0.3170 0.0725 Uiso 1.0000 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . . 1.521(2) n
    C1 O1 . . 1.416(2) n
    C1 S1 . . 1.8398(16) n
    C1 H11 . . 0.984 no
    C2 C3 . . 1.520(2) n
    C2 O3 . . 1.4464(18) n
    C2 H21 . . 0.988 no
    C3 C4 . . 1.511(2) n
    C3 O5 . . 1.443(2) n
    C3 H31 . . 0.990 no
    C4 C5 . . 1.525(2) n
    C4 O7 . . 1.443(2) n
    C4 H41 . . 0.972 no
    C5 C6 . . 1.509(2) n
    C5 O1 . . 1.439(2) n
    C5 H51 . . 0.995 no
    C6 O9 . . 1.443(2) n
    C6 H61 . . 0.977 no
    C6 H62 . . 0.998 no
    S1 C7 . . 1.7770(18) n
    C7 C8 . . 1.392(3) n
    C7 C12 . . 1.385(3) n
    C8 C9 . . 1.385(3) n
    C8 H81 . . 0.965 no
    C9 C10 . . 1.390(3) n
    C9 H91 . . 0.969 no
    C10 C11 . . 1.384(3) n
    C10 O2 . . 1.362(2) n
    C11 C12 . . 1.395(3) n
    C11 H111 . . 0.984 no
    C12 H121 . . 0.984 no
    O2 C13 . . 1.432(3) n
    C13 H131 . . 0.985 no
    C13 H132 . . 0.987 no
    C13 H133 . . 0.994 no
    O3 C14 . . 1.349(2) n
    C14 O4 . . 1.200(3) n
    C14 C15 . . 1.492(3) n
    C15 H152 . . 0.975 no
    C15 H151 . . 0.970 no
    C15 H153 . . 0.978 no
    O5 C16 . . 1.337(2) n
    C16 O6 . . 1.201(3) n
    C16 C17 . . 1.496(3) n
    C17 H172 . . 0.962 no
    C17 H171 . . 0.952 no
    C17 H173 . . 0.980 no
    O7 C18 . . 1.370(2) n
    C18 O8 . . 1.197(2) n
    C18 C19 . . 1.486(3) n
    C19 H192 . . 0.961 no
    C19 H191 . . 0.973 no
    C19 H193 . . 0.983 no
    O9 C20 . . 1.350(2) n
    C20 O10 . . 1.206(3) n
    C20 C21 . . 1.490(3) n
    C21 H212 . . 0.973 no
    C21 H211 . . 0.953 no
    C21 H213 . . 0.974 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . . 112.11(13) n
    C2 C1 S1 . . . 108.09(12) n
    O1 C1 S1 . . . 113.96(11) n
    C2 C1 H11 . . . 108.5 no
    O1 C1 H11 . . . 107.4 no
    S1 C1 H11 . . . 106.4 no
    C1 C2 C3 . . . 110.61(14) n
    C1 C2 O3 . . . 106.83(13) n
    C3 C2 O3 . . . 108.29(13) n
    C1 C2 H21 . . . 110.4 no
    C3 C2 H21 . . . 111.1 no
    O3 C2 H21 . . . 109.4 no
    C2 C3 C4 . . . 110.96(14) n
    C2 C3 O5 . . . 110.06(14) n
    C4 C3 O5 . . . 107.35(14) n
    C2 C3 H31 . . . 109.6 no
    C4 C3 H31 . . . 108.9 no
    O5 C3 H31 . . . 109.9 no
    C3 C4 C5 . . . 108.45(13) n
    C3 C4 O7 . . . 109.09(13) n
    C5 C4 O7 . . . 106.10(13) n
    C3 C4 H41 . . . 110.2 no
    C5 C4 H41 . . . 112.4 no
    O7 C4 H41 . . . 110.4 no
    C4 C5 C6 . . . 113.78(14) n
    C4 C5 O1 . . . 110.03(13) n
    C6 C5 O1 . . . 107.28(14) n
    C4 C5 H51 . . . 109.3 no
    C6 C5 H51 . . . 106.9 no
    O1 C5 H51 . . . 109.5 no
    C5 C6 O9 . . . 108.34(13) n
    C5 C6 H61 . . . 110.6 no
    O9 C6 H61 . . . 109.7 no
    C5 C6 H62 . . . 109.5 no
    O9 C6 H62 . . . 110.1 no
    H61 C6 H62 . . . 108.6 no
    C5 O1 C1 . . . 114.46(13) n
    C1 S1 C7 . . . 100.12(8) n
    S1 C7 C8 . . . 120.59(14) n
    S1 C7 C12 . . . 120.12(14) n
    C8 C7 C12 . . . 119.28(17) n
    C7 C8 C9 . . . 120.06(18) n
    C7 C8 H81 . . . 120.0 no
    C9 C8 H81 . . . 119.9 no
    C8 C9 C10 . . . 120.60(18) n
    C8 C9 H91 . . . 119.3 no
    C10 C9 H91 . . . 120.1 no
    C9 C10 C11 . . . 119.57(17) n
    C9 C10 O2 . . . 115.99(17) n
    C11 C10 O2 . . . 124.43(18) n
    C10 C11 C12 . . . 119.80(18) n
    C10 C11 H111 . . . 119.7 no
    C12 C11 H111 . . . 120.4 no
    C11 C12 C7 . . . 120.66(17) n
    C11 C12 H121 . . . 120.0 no
    C7 C12 H121 . . . 119.3 no
    C10 O2 C13 . . . 117.93(17) n
    O2 C13 H131 . . . 106.9 no
    O2 C13 H132 . . . 109.7 no
    H131 C13 H132 . . . 113.0 no
    O2 C13 H133 . . . 108.5 no
    H131 C13 H133 . . . 108.5 no
    H132 C13 H133 . . . 110.1 no
    C2 O3 C14 . . . 117.36(14) n
    O3 C14 O4 . . . 123.21(18) n
    O3 C14 C15 . . . 111.29(17) n
    O4 C14 C15 . . . 125.49(19) n
    C14 C15 H152 . . . 110.1 no
    C14 C15 H151 . . . 109.4 no
    H152 C15 H151 . . . 108.9 no
    C14 C15 H153 . . . 109.0 no
    H152 C15 H153 . . . 111.7 no
    H151 C15 H153 . . . 107.8 no
    C3 O5 C16 . . . 117.69(15) n
    O5 C16 O6 . . . 122.6(2) n
    O5 C16 C17 . . . 110.9(2) n
    O6 C16 C17 . . . 126.5(2) n
    C16 C17 H172 . . . 108.0 no
    C16 C17 H171 . . . 108.1 no
    H172 C17 H171 . . . 112.4 no
    C16 C17 H173 . . . 108.7 no
    H172 C17 H173 . . . 108.6 no
    H171 C17 H173 . . . 110.9 no
    C4 O7 C18 . . . 117.88(13) n
    O7 C18 O8 . . . 123.04(17) n
    O7 C18 C19 . . . 110.42(16) n
    O8 C18 C19 . . . 126.54(18) n
    C18 C19 H192 . . . 108.6 no
    C18 C19 H191 . . . 109.5 no
    H192 C19 H191 . . . 110.7 no
    C18 C19 H193 . . . 110.3 no
    H192 C19 H193 . . . 109.9 no
    H191 C19 H193 . . . 107.8 no
    C6 O9 C20 . . . 114.75(14) n
    O9 C20 O10 . . . 122.1(2) n
    O9 C20 C21 . . . 111.87(17) n
    O10 C20 C21 . . . 126.01(19) n
    C20 C21 H212 . . . 109.7 no
    C20 C21 H211 . . . 108.2 no
    H212 C21 H211 . . . 109.9 no
    C20 C21 H213 . . . 110.2 no
    H212 C21 H213 . . . 108.9 no
    H211 C21 H213 . . . 110.0 no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C1 H11 O10 . . 1_655 0.98 2.40 3.248(3) 144 yes
    C19 H191 O2 . . 2_456 0.97 2.54 3.362(3) 142 yes
    C21 H213 O6 . . 4_564 0.97 2.43 3.143(3) 130 yes
data_global
_journal_date_recd_electronic     2008-06-19
_journal_date_accepted     2008-06-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1401
_journal_page_last     o1401
_journal_paper_category     QO
_journal_coeditor_code     LH2646
_publ_contact_author_name     'Antony J. Fairbanks'
_publ_contact_author_address
;
Chemistry Research Laboratory
Mansfield Road
Oxford, OX1 3TA, UK.
;
_publ_contact_author_email     antony.fairbanks@chem.ox.ac.uk
_publ_contact_author_fax     '+441865275674'
_publ_contact_author_phone     '+441865275647'
_publ_section_title
;
4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Drouin, Ludovic' .
;
Chemistry Research Laboratory
Mansfield Road
Oxford OX1 3TA
England
;
    'Cowley, Andrew R.' .
;
Chemical Crystallography Department,
Chemistry Research Laboratory,
University of Oxford,
Mansfield Road,
Oxford OX1 3TA
England
;
    'Fairbanks, Antony J.' .
;
Chemistry Research Laboratory
Mansfield Road
Oxford OX1 3TA
England
;
    'Thompson, Amber L.' .
;
Chemical Crystallography Department,
Chemistry Research Laboratory,
University of Oxford,
Mansfield Road,
Oxford OX1 3TA
England
;
