#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017568.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_2017568
loop_
_publ_author_name
'Dedola, Simone'
'Hughes, David L.'
'Field, Robert A.'
_publ_section_title
;
 Peracetylated α-<small>D</small>-glucopyranosyl fluoride and
 peracetylated α-maltosyl fluoride
;
_journal_coeditor_code           JZ3170
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o124
_journal_page_last               o127
_journal_paper_doi               10.1107/S0108270110003641
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H19 F O9'
_chemical_formula_moiety         'C14 H19 F O9'
_chemical_formula_structural     'C14 H19 F O9'
_chemical_formula_sum            'C14 H19 F O9'
_chemical_formula_weight         350.29
_chemical_name_common            2,3,4,6-tetraacetyl-1-fluoro-α-D-glucopyranose
_chemical_name_systematic
2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 and CrysAlisPro RED'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.061(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.35502(11)
_cell_length_b                   7.96182(14)
_cell_length_c                   20.1151(5)
_cell_measurement_temperature    140.0(10)
_cell_volume                     857.07(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics
;
ORTEP (Johnson, 1976; Farrugia, 1997)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140.0(10)
_diffrn_detector_area_resol_mean 16.0050
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Xcalibur 3 CCD area-detector'
_diffrn_measurement_method       'thin-slice φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24426
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.033
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2677
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0325
_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)+(0.0461P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                2325
_reflns_number_total             2677
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz3170.cif
_cod_data_source_block           I
_cod_original_cell_volume        857.06(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2017568
_cod_database_fobs_code          2017568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C C1 0.6033(3) 0.0924(2) 0.77495(8) 0.0328(4) Uani d . 1 . .
H H1 0.6134 -0.0175 0.7969 0.039 Uiso calc R 1 . .
F F1 0.35222(18) 0.12992(12) 0.76037(5) 0.0404(3) Uani d . 1 . .
C C2 0.7110(3) 0.2240(2) 0.82211(8) 0.0328(4) Uani d . 1 . .
H H2 0.8718 0.1842 0.8409 0.039 Uiso calc R 1 . .
O O2 0.5423(2) 0.2501(2) 0.87516(6) 0.0439(3) Uani d . 1 . .
C C21 0.5919(3) 0.1744(2) 0.93372(8) 0.0318(4) Uani d . 1 . .
O O21 0.7746(2) 0.0915(2) 0.94472(6) 0.0452(3) Uani d . 1 . .
C C22 0.3888(4) 0.2075(3) 0.98137(10) 0.0472(5) Uani d . 1 . .
H H22A 0.2421 0.2465 0.9573 0.071 Uiso calc PR 0.25(3) . .
H H22B 0.4436 0.2914 1.0129 0.071 Uiso calc PR 0.25(3) . .
H H22C 0.3507 0.1057 1.0045 0.071 Uiso calc PR 0.25(3) . .
H H22D 0.4488 0.1825 1.0258 0.071 Uiso calc PR 0.75(3) . .
H H22E 0.2473 0.1376 0.9702 0.071 Uiso calc PR 0.75(3) . .
H H22F 0.3403 0.3234 0.9786 0.071 Uiso calc PR 0.75(3) . .
C C3 0.7486(3) 0.3919(2) 0.78877(8) 0.0284(3) Uani d . 1 . .
H H3 0.5886 0.4499 0.7813 0.034 Uiso calc R 1 . .
O O3 0.9140(2) 0.48888(16) 0.83218(6) 0.0364(3) Uani d . 1 . .
C C31 0.8463(3) 0.6464(2) 0.84832(8) 0.0306(3) Uani d . 1 . .
O O31 0.6465(2) 0.70525(15) 0.83370(7) 0.0394(3) Uani d . 1 . .
C C32 1.0518(3) 0.7312(3) 0.88735(10) 0.0458(5) Uani d . 1 . .
H H32A 0.9960 0.8395 0.9017 0.069 Uiso calc R 1 . .
H H32B 1.1937 0.7446 0.8600 0.069 Uiso calc R 1 . .
H H32C 1.0980 0.6642 0.9255 0.069 Uiso calc R 1 . .
C C4 0.8793(3) 0.36885(18) 0.72381(8) 0.0246(3) Uani d . 1 . .
H H4 1.0515 0.3313 0.7327 0.029 Uiso calc R 1 . .
O O4 0.8793(2) 0.53069(13) 0.69203(6) 0.0287(2) Uani d . 1 . .
C C41 1.1004(3) 0.5908(2) 0.67263(8) 0.0292(3) Uani d . 1 . .
O O41 1.2878(2) 0.51069(18) 0.67489(8) 0.0493(4) Uani d . 1 . .
C C42 1.0749(4) 0.7672(2) 0.64776(10) 0.0412(4) Uani d . 1 . .
H H42A 0.9049 0.7874 0.6332 0.062 Uiso calc PR 0.39(2) . .
H H42B 1.1827 0.7836 0.6112 0.062 Uiso calc PR 0.39(2) . .
H H42C 1.1209 0.8440 0.6829 0.062 Uiso calc PR 0.39(2) . .
H H42D 1.2341 0.8226 0.6517 0.062 Uiso calc PR 0.61(2) . .
H H42E 0.9563 0.8264 0.6737 0.062 Uiso calc PR 0.61(2) . .
H H42F 1.0181 0.7660 0.6020 0.062 Uiso calc PR 0.61(2) . .
C C5 0.7405(3) 0.24153(19) 0.68033(8) 0.0250(3) Uani d . 1 . .
H H5 0.5703 0.2814 0.6701 0.030 Uiso calc R 1 . .
O O5 0.7315(2) 0.08485(13) 0.71669(6) 0.0297(2) Uani d . 1 . .
C C6 0.8690(3) 0.20300(19) 0.61687(7) 0.0265(3) Uani d . 1 . .
H H6A 0.8979 0.3053 0.5921 0.032 Uiso calc R 1 . .
H H6B 1.0283 0.1485 0.6263 0.032 Uiso calc R 1 . .
O O6 0.7027(2) 0.09256(14) 0.57958(5) 0.0288(2) Uani d . 1 . .
C C61 0.7852(3) 0.0334(2) 0.52204(8) 0.0276(3) Uani d . 1 . .
O O61 0.9860(2) 0.06861(17) 0.50114(7) 0.0382(3) Uani d . 1 . .
C C62 0.5989(3) -0.0825(2) 0.48918(10) 0.0385(4) Uani d . 1 . .
H H62A 0.4429 -0.0743 0.5110 0.058 Uiso calc PR 0.78(2) . .
H H62B 0.6596 -0.1958 0.4922 0.058 Uiso calc PR 0.78(2) . .
H H62C 0.5747 -0.0519 0.4432 0.058 Uiso calc PR 0.78(2) . .
H H62D 0.6752 -0.1404 0.4533 0.058 Uiso calc PR 0.22(2) . .
H H62E 0.4585 -0.0188 0.4721 0.058 Uiso calc PR 0.22(2) . .
H H62F 0.5434 -0.1628 0.5211 0.058 Uiso calc PR 0.22(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'
F F 0.0171 0.0103 '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
O5 C1 F1 . . 109.58(13) ?
O5 C1 C2 . . 111.84(14) ?
F1 C1 C2 . . 108.98(13) ?
O5 C1 H1 . . 108.8 ?
F1 C1 H1 . . 108.8 ?
C2 C1 H1 . . 108.8 ?
O2 C2 C3 . . 107.38(14) ?
O2 C2 C1 . . 109.25(15) ?
C3 C2 C1 . . 112.83(13) ?
O2 C2 H2 . . 109.1 ?
C3 C2 H2 . . 109.1 ?
C1 C2 H2 . . 109.1 ?
C21 O2 C2 . . 118.48(13) ?
O21 C21 O2 . . 123.11(15) ?
O21 C21 C22 . . 125.95(17) ?
O2 C21 C22 . . 110.93(16) ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C21 C22 H22D . . 109.5 ?
H22A C22 H22D . . 141.1 ?
H22B C22 H22D . . 56.3 ?
H22C C22 H22D . . 56.3 ?
C21 C22 H22E . . 109.5 ?
H22A C22 H22E . . 56.3 ?
H22B C22 H22E . . 141.1 ?
H22C C22 H22E . . 56.3 ?
H22D C22 H22E . . 109.5 ?
C21 C22 H22F . . 109.5 ?
H22A C22 H22F . . 56.3 ?
H22B C22 H22F . . 56.3 ?
H22C C22 H22F . . 141.1 ?
H22D C22 H22F . . 109.5 ?
H22E C22 H22F . . 109.5 ?
O3 C3 C2 . . 107.03(13) ?
O3 C3 C4 . . 107.09(13) ?
C2 C3 C4 . . 110.39(13) ?
O3 C3 H3 . . 110.7 ?
C2 C3 H3 . . 110.7 ?
C4 C3 H3 . . 110.7 ?
C31 O3 C3 . . 118.57(13) ?
O31 C31 O3 . . 123.49(16) ?
O31 C31 C32 . . 126.11(17) ?
O3 C31 C32 . . 110.39(15) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
O4 C4 C3 . . 106.38(12) ?
O4 C4 C5 . . 110.52(11) ?
C3 C4 C5 . . 110.27(13) ?
O4 C4 H4 . . 109.9 ?
C3 C4 H4 . . 109.9 ?
C5 C4 H4 . . 109.9 ?
C41 O4 C4 . . 117.43(12) ?
O41 C41 O4 . . 123.20(15) ?
O41 C41 C42 . . 125.72(17) ?
O4 C41 C42 . . 111.08(14) ?
C41 C42 H42A . . 109.5 ?
C41 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C41 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C41 C42 H42D . . 109.5 ?
H42A C42 H42D . . 141.1 ?
H42B C42 H42D . . 56.3 ?
H42C C42 H42D . . 56.3 ?
C41 C42 H42E . . 109.5 ?
H42A C42 H42E . . 56.3 ?
H42B C42 H42E . . 141.1 ?
H42C C42 H42E . . 56.3 ?
H42D C42 H42E . . 109.5 ?
C41 C42 H42F . . 109.5 ?
H42A C42 H42F . . 56.3 ?
H42B C42 H42F . . 56.3 ?
H42C C42 H42F . . 141.1 ?
H42D C42 H42F . . 109.5 ?
H42E C42 H42F . . 109.5 ?
O5 C5 C6 . . 106.12(12) ?
O5 C5 C4 . . 108.02(11) ?
C6 C5 C4 . . 113.36(13) ?
O5 C5 H5 . . 109.7 ?
C6 C5 H5 . . 109.7 ?
C4 C5 H5 . . 109.7 ?
C1 O5 C5 . . 114.70(12) ?
O6 C6 C5 . . 105.85(12) ?
O6 C6 H6A . . 110.6 ?
C5 C6 H6A . . 110.6 ?
O6 C6 H6B . . 110.6 ?
C5 C6 H6B . . 110.6 ?
H6A C6 H6B . . 108.7 ?
C61 O6 C6 . . 116.57(12) ?
O61 C61 O6 . . 123.18(15) ?
O61 C61 C62 . . 125.47(16) ?
O6 C61 C62 . . 111.33(14) ?
C61 C62 H62A . . 109.5 ?
C61 C62 H62B . . 109.5 ?
H62A C62 H62B . . 109.5 ?
C61 C62 H62C . . 109.5 ?
H62A C62 H62C . . 109.5 ?
H62B C62 H62C . . 109.5 ?
C61 C62 H62D . . 109.5 ?
H62A C62 H62D . . 141.1 ?
H62B C62 H62D . . 56.3 ?
H62C C62 H62D . . 56.3 ?
C61 C62 H62E . . 109.5 ?
H62A C62 H62E . . 56.3 ?
H62B C62 H62E . . 141.1 ?
H62C C62 H62E . . 56.3 ?
H62D C62 H62E . . 109.5 ?
C61 C62 H62F . . 109.5 ?
H62A C62 H62F . . 56.3 ?
H62B C62 H62F . . 56.3 ?
H62C C62 H62F . . 141.1 ?
H62D C62 H62F . . 109.5 ?
H62E C62 H62F . . 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
C1 O5 . 1.381(2) ?
C1 F1 . 1.3981(19) ?
C1 C2 . 1.514(3) ?
C1 H1 . 0.9800 ?
C2 O2 . 1.4378(19) ?
C2 C3 . 1.512(2) ?
C2 H2 . 0.9800 ?
O2 C21 . 1.341(2) ?
C21 O21 . 1.194(2) ?
C21 C22 . 1.499(2) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C22 H22D . 0.9600 ?
C22 H22E . 0.9600 ?
C22 H22F . 0.9600 ?
C3 O3 . 1.445(2) ?
C3 C4 . 1.515(2) ?
C3 H3 . 0.9800 ?
O3 C31 . 1.348(2) ?
C31 O31 . 1.195(2) ?
C31 C32 . 1.490(3) ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
C4 O4 . 1.4384(18) ?
C4 C5 . 1.516(2) ?
C4 H4 . 0.9800 ?
O4 C41 . 1.348(2) ?
C41 O41 . 1.188(2) ?
C41 C42 . 1.496(2) ?
C42 H42A . 0.9600 ?
C42 H42B . 0.9600 ?
C42 H42C . 0.9600 ?
C42 H42D . 0.9600 ?
C42 H42E . 0.9600 ?
C42 H42F . 0.9600 ?
C5 O5 . 1.4477(18) ?
C5 C6 . 1.503(2) ?
C5 H5 . 0.9800 ?
C6 O6 . 1.4424(18) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
O6 C61 . 1.339(2) ?
C61 O61 . 1.202(2) ?
C61 C62 . 1.495(2) ?
C62 H62A . 0.9600 ?
C62 H62B . 0.9600 ?
C62 H62C . 0.9600 ?
C62 H62D . 0.9600 ?
C62 H62E . 0.9600 ?
C62 H62F . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 C1 C2 O2 . . . . 168.42(12) ?
F1 C1 C2 O2 . . . . 47.11(17) ?
O5 C1 C2 C3 . . . . 49.06(17) ?
F1 C1 C2 C3 . . . . -72.25(16) ?
C3 C2 O2 C21 . . . . -137.54(16) ?
C1 C2 O2 C21 . . . . 99.78(17) ?
C2 O2 C21 O21 . . . . 3.0(3) ?
C2 O2 C21 C22 . . . . -176.58(17) ?
O2 C2 C3 O3 . . . . 75.69(16) ?
C1 C2 C3 O3 . . . . -163.87(13) ?
O2 C2 C3 C4 . . . . -168.09(13) ?
C1 C2 C3 C4 . . . . -47.66(18) ?
C2 C3 O3 C31 . . . . -129.48(15) ?
C4 C3 O3 C31 . . . . 112.13(15) ?
C3 O3 C31 O31 . . . . 7.1(2) ?
C3 O3 C31 C32 . . . . -174.11(15) ?
O3 C3 C4 O4 . . . . -70.72(14) ?
C2 C3 C4 O4 . . . . 173.10(13) ?
O3 C3 C4 C5 . . . . 169.42(11) ?
C2 C3 C4 C5 . . . . 53.23(16) ?
C3 C4 O4 C41 . . . . 127.16(14) ?
C5 C4 O4 C41 . . . . -113.13(14) ?
C4 O4 C41 O41 . . . . 7.2(2) ?
C4 O4 C41 C42 . . . . -173.47(14) ?
O4 C4 C5 O5 . . . . -176.06(12) ?
C3 C4 C5 O5 . . . . -58.72(15) ?
O4 C4 C5 C6 . . . . 66.65(15) ?
C3 C4 C5 C6 . . . . -176.01(13) ?
F1 C1 O5 C5 . . . . 63.56(18) ?
C2 C1 O5 C5 . . . . -57.40(16) ?
C6 C5 O5 C1 . . . . -175.67(13) ?
C4 C5 O5 C1 . . . . 62.46(16) ?
O5 C5 C6 O6 . . . . 66.43(14) ?
C4 C5 C6 O6 . . . . -175.17(11) ?
C5 C6 O6 C61 . . . . -176.41(12) ?
C6 O6 C61 O61 . . . . -0.2(2) ?
C6 O6 C61 C62 . . . . 178.56(13) ?
