#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/96/2229629.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_2229629
loop_
_publ_author_name
'Heidelberg, Thorsten'
'Hussen, Rusnah Syahila Duali'
'Rodzi, Nasrul Zamani Mohd'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4-Formylphenyl
 2,3,4,6-tetra-O-acetyl-β-<small>D</small>-glucopyranoside
;
_journal_coeditor_code           EZ2235
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o825
_journal_paper_doi               10.1107/S1600536811008099
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H24 O11'
_chemical_formula_moiety         'C21 H24 O11'
_chemical_formula_sum            'C21 H24 O11'
_chemical_formula_weight         452.40
_chemical_name_systematic
;
4-Formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
;
_space_group_IT_number           1
_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                102.473(3)
_cell_angle_beta                 93.481(2)
_cell_angle_gamma                102.780(3)
_cell_formula_units_Z            1
_cell_length_a                   5.7868(2)
_cell_length_b                   8.9166(3)
_cell_length_c                   11.4716(3)
_cell_measurement_reflns_used    7285
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.1
_cell_measurement_theta_min      4.0
_cell_volume                     559.96(3)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent Technologies, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent Technologies, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type
;
Agilent Supernova Dual diffractometer with an Atlas detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7392
_diffrn_reflns_theta_full        74.3
_diffrn_reflns_theta_max         74.3
_diffrn_reflns_theta_min         4.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent Technologies, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983), 1855 Friedel pairs'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.041
_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)+(0.0908P)²+0.072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.115
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                4087
_reflns_number_total             4097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2235.cif
_cod_data_source_block           I
_cod_database_code               2229629
_cod_database_fobs_code          2229629
loop_
_symmetry_equiv_pos_as_xyz
'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
O O1 0.9987(2) 0.49931(15) 0.49910(11) 0.0174(3) Uani d . 1 . .
O O2 1.0120(2) 0.81529(16) 0.57609(11) 0.0218(3) Uani d . 1 . .
O O3 0.7432(3) 0.95346(19) 0.63881(14) 0.0305(3) Uani d . 1 . .
O O4 0.7892(2) 0.55996(15) 0.20730(10) 0.0167(3) Uani d . 1 . .
O O5 0.4356(2) 0.59974(16) 0.26001(12) 0.0208(3) Uani d . 1 . .
O O6 0.7723(2) 0.23423(15) 0.15960(11) 0.0192(3) Uani d . 1 . .
O O7 1.0136(3) 0.2794(2) 0.01679(14) 0.0385(4) Uani d . 1 . .
O O8 1.1640(2) 0.17486(15) 0.30105(11) 0.0196(3) Uani d . 1 . .
O O9 0.8768(3) -0.04604(17) 0.28892(15) 0.0297(3) Uani d . 1 . .
O O10 1.1933(2) 0.31718(15) 0.54454(11) 0.0204(3) Uani d . 1 . .
O O11 2.0808(3) 0.73176(19) 0.92751(14) 0.0330(4) Uani d . 1 . .
C C1 0.9617(3) 0.5930(2) 0.41525(15) 0.0166(3) Uani d . 1 . .
H H1 1.1190 0.6460 0.3937 0.020 Uiso calc R 1 . .
C C2 0.8116(3) 0.4800(2) 0.30264(15) 0.0155(3) Uani d . 1 . .
H H2 0.6503 0.4316 0.3225 0.019 Uiso calc R 1 . .
C C3 0.9368(3) 0.3515(2) 0.25138(15) 0.0163(3) Uani d . 1 . .
H H3 1.0817 0.3980 0.2159 0.020 Uiso calc R 1 . .
C C4 1.0071(3) 0.2710(2) 0.34749(16) 0.0171(3) Uani d . 1 . .
H H4 0.8624 0.2051 0.3712 0.021 Uiso calc R 1 . .
C C5 1.1452(3) 0.3968(2) 0.45629(15) 0.0168(3) Uani d . 1 . .
H H5 1.2968 0.4572 0.4343 0.020 Uiso calc R 1 . .
C C6 0.8401(3) 0.7168(2) 0.47781(16) 0.0187(3) Uani d . 1 . .
H H6A 0.7979 0.7799 0.4222 0.022 Uiso calc R 1 . .
H H6B 0.6930 0.6665 0.5080 0.022 Uiso calc R 1 . .
C C7 0.9388(3) 0.9279(2) 0.65168(16) 0.0220(4) Uani d . 1 . .
C C8 1.1278(4) 1.0105(3) 0.75474(18) 0.0291(4) Uani d . 1 . .
H H8A 1.1138 1.1193 0.7845 0.044 Uiso calc R 1 . .
H H8B 1.2855 1.0119 0.7277 0.044 Uiso calc R 1 . .
H H8C 1.1077 0.9543 0.8194 0.044 Uiso calc R 1 . .
C C9 0.5824(3) 0.6053(2) 0.19069(15) 0.0163(3) Uani d . 1 . .
C C10 0.5674(3) 0.6549(3) 0.07482(17) 0.0234(4) Uani d . 1 . .
H H10A 0.4287 0.7001 0.0685 0.035 Uiso calc R 1 . .
H H10B 0.5507 0.5627 0.0077 0.035 Uiso calc R 1 . .
H H10C 0.7128 0.7344 0.0721 0.035 Uiso calc R 1 . .
C C11 0.8311(4) 0.2113(2) 0.04513(17) 0.0250(4) Uani d . 1 . .
C C12 0.6319(5) 0.0922(3) -0.0371(2) 0.0428(6) Uani d . 1 . .
H H12A 0.6747 0.0749 -0.1195 0.064 Uiso calc R 1 . .
H H12B 0.4866 0.1315 -0.0340 0.064 Uiso calc R 1 . .
H H12C 0.6041 -0.0078 -0.0117 0.064 Uiso calc R 1 . .
C C13 1.0775(3) 0.0158(2) 0.27726(16) 0.0214(4) Uani d . 1 . .
C C14 1.2625(4) -0.0679(3) 0.2328(3) 0.0385(5) Uani d . 1 . .
H H14A 1.1877 -0.1802 0.1990 0.058 Uiso calc R 1 . .
H H14B 1.3833 -0.0573 0.2997 0.058 Uiso calc R 1 . .
H H14C 1.3381 -0.0212 0.1706 0.058 Uiso calc R 1 . .
C C15 1.3937(3) 0.3914(2) 0.62530(15) 0.0185(4) Uani d . 1 . .
C C16 1.5446(4) 0.2974(3) 0.64956(18) 0.0230(4) Uani d . 1 . .
H H16 1.5095 0.1883 0.6104 0.028 Uiso calc R 1 . .
C C17 1.7455(4) 0.3644(3) 0.73110(18) 0.0249(4) Uani d . 1 . .
H H17 1.8490 0.3008 0.7482 0.030 Uiso calc R 1 . .
C C18 1.7984(3) 0.5252(2) 0.78886(16) 0.0229(4) Uani d . 1 . .
C C19 1.6452(3) 0.6178(2) 0.76354(15) 0.0216(4) Uani d . 1 . .
H H19 1.6803 0.7268 0.8028 0.026 Uiso calc R 1 . .
C C20 1.4427(3) 0.5528(2) 0.68196(16) 0.0209(4) Uani d . 1 . .
H H20 1.3390 0.6162 0.6647 0.025 Uiso calc R 1 . .
C C21 2.0148(4) 0.5937(3) 0.87497(18) 0.0279(4) Uani d . 1 . .
H H21 2.1099 0.5244 0.8905 0.034 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C5 O1 C1 . . 111.07(12) ?
C7 O2 C6 . . 116.65(14) ?
C9 O4 C2 . . 117.18(13) ?
C11 O6 C3 . . 117.74(14) ?
C13 O8 C4 . . 117.05(14) ?
C15 O10 C5 . . 115.77(13) ?
O1 C1 C6 . . 106.88(13) ?
O1 C1 C2 . . 107.27(13) ?
C6 C1 C2 . . 113.52(14) ?
O1 C1 H1 . . 109.7 ?
C6 C1 H1 . . 109.7 ?
C2 C1 H1 . . 109.7 ?
O4 C2 C3 . . 104.57(13) ?
O4 C2 C1 . . 111.42(13) ?
C3 C2 C1 . . 110.19(13) ?
O4 C2 H2 . . 110.2 ?
C3 C2 H2 . . 110.2 ?
C1 C2 H2 . . 110.2 ?
O6 C3 C2 . . 107.91(13) ?
O6 C3 C4 . . 108.09(14) ?
C2 C3 C4 . . 111.16(13) ?
O6 C3 H3 . . 109.9 ?
C2 C3 H3 . . 109.9 ?
C4 C3 H3 . . 109.9 ?
O8 C4 C3 . . 108.55(14) ?
O8 C4 C5 . . 107.52(13) ?
C3 C4 C5 . . 109.22(14) ?
O8 C4 H4 . . 110.5 ?
C3 C4 H4 . . 110.5 ?
C5 C4 H4 . . 110.5 ?
O10 C5 O1 . . 109.38(13) ?
O10 C5 C4 . . 106.87(14) ?
O1 C5 C4 . . 108.50(13) ?
O10 C5 H5 . . 110.7 ?
O1 C5 H5 . . 110.7 ?
C4 C5 H5 . . 110.7 ?
O2 C6 C1 . . 105.19(14) ?
O2 C6 H6A . . 110.7 ?
C1 C6 H6A . . 110.7 ?
O2 C6 H6B . . 110.7 ?
C1 C6 H6B . . 110.7 ?
H6A C6 H6B . . 108.8 ?
O3 C7 O2 . . 123.64(17) ?
O3 C7 C8 . . 125.73(18) ?
O2 C7 C8 . . 110.58(16) ?
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 . . 122.82(15) ?
O5 C9 C10 . . 127.05(16) ?
O4 C9 C10 . . 110.10(14) ?
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 . . 124.08(17) ?
O7 C11 C12 . . 126.49(19) ?
O6 C11 C12 . . 109.41(17) ?
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 . . 123.37(18) ?
O9 C13 C14 . . 125.80(19) ?
O8 C13 C14 . . 110.81(17) ?
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 ?
O10 C15 C16 . . 116.66(17) ?
O10 C15 C20 . . 122.13(16) ?
C16 C15 C20 . . 121.21(17) ?
C17 C16 C15 . . 119.31(19) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C16 C17 C18 . . 120.59(17) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C19 C18 C17 . . 119.37(17) ?
C19 C18 C21 . . 121.21(18) ?
C17 C18 C21 . . 119.42(18) ?
C20 C19 C18 . . 120.91(18) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C19 C20 C15 . . 118.61(17) ?
C19 C20 H20 . . 120.7 ?
C15 C20 H20 . . 120.7 ?
O11 C21 C18 . . 124.9(2) ?
O11 C21 H21 . . 117.5 ?
C18 C21 H21 . . 117.5 ?
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
O1 C5 . 1.413(2) ?
O1 C1 . 1.439(2) ?
O2 C7 . 1.340(2) ?
O2 C6 . 1.443(2) ?
O3 C7 . 1.210(3) ?
O4 C9 . 1.361(2) ?
O4 C2 . 1.443(2) ?
O5 C9 . 1.199(2) ?
O6 C11 . 1.360(2) ?
O6 C3 . 1.4389(19) ?
O7 C11 . 1.197(3) ?
O8 C13 . 1.356(2) ?
O8 C4 . 1.431(2) ?
O9 C13 . 1.199(3) ?
O10 C15 . 1.381(2) ?
O10 C5 . 1.404(2) ?
O11 C21 . 1.212(3) ?
C1 C6 . 1.513(2) ?
C1 C2 . 1.534(2) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.521(2) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.520(2) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.527(2) ?
C4 H4 . 1.0000 ?
C5 H5 . 1.0000 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.499(3) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.492(2) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.497(3) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.489(3) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 C16 . 1.391(3) ?
C15 C20 . 1.403(3) ?
C16 C17 . 1.380(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.400(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.396(3) ?
C18 C21 . 1.472(3) ?
C19 C20 . 1.384(3) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
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 O5 1_655 1.00 2.51 3.356(2) 143
C3 H3 O5 1_655 1.00 2.35 3.207(2) 143
C6 H6A O9 1_565 0.99 2.40 3.324(2) 155
C8 H8C O11 1_455 0.98 2.54 3.475(3) 160
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
C5 O1 C1 C6 . . . . -170.55(13) ?
C5 O1 C1 C2 . . . . 67.38(15) ?
C9 O4 C2 C3 . . . . 140.73(14) ?
C9 O4 C2 C1 . . . . -100.26(16) ?
O1 C1 C2 O4 . . . . -173.01(13) ?
C6 C1 C2 O4 . . . . 69.16(17) ?
O1 C1 C2 C3 . . . . -57.40(16) ?
C6 C1 C2 C3 . . . . -175.23(13) ?
C11 O6 C3 C2 . . . . 117.13(16) ?
C11 O6 C3 C4 . . . . -122.56(16) ?
O4 C2 C3 O6 . . . . -69.99(15) ?
C1 C2 C3 O6 . . . . 170.17(13) ?
O4 C2 C3 C4 . . . . 171.65(13) ?
C1 C2 C3 C4 . . . . 51.81(18) ?
C13 O8 C4 C3 . . . . -110.11(16) ?
C13 O8 C4 C5 . . . . 131.85(15) ?
O6 C3 C4 O8 . . . . 73.14(16) ?
C2 C3 C4 O8 . . . . -168.61(13) ?
O6 C3 C4 C5 . . . . -169.91(13) ?
C2 C3 C4 C5 . . . . -51.66(18) ?
C15 O10 C5 O1 . . . . -89.74(17) ?
C15 O10 C5 C4 . . . . 152.99(14) ?
C1 O1 C5 O10 . . . . 175.14(12) ?
C1 O1 C5 C4 . . . . -68.62(16) ?
O8 C4 C5 O10 . . . . -65.78(16) ?
C3 C4 C5 O10 . . . . 176.62(13) ?
O8 C4 C5 O1 . . . . 176.37(13) ?
C3 C4 C5 O1 . . . . 58.77(17) ?
C7 O2 C6 C1 . . . . -174.96(14) ?
O1 C1 C6 O2 . . . . 64.96(16) ?
C2 C1 C6 O2 . . . . -176.99(13) ?
C6 O2 C7 O3 . . . . -2.8(3) ?
C6 O2 C7 C8 . . . . 174.88(15) ?
C2 O4 C9 O5 . . . . 9.6(2) ?
C2 O4 C9 C10 . . . . -168.33(15) ?
C3 O6 C11 O7 . . . . 2.1(3) ?
C3 O6 C11 C12 . . . . -176.77(19) ?
C4 O8 C13 O9 . . . . 2.9(3) ?
C4 O8 C13 C14 . . . . -178.48(17) ?
C5 O10 C15 C16 . . . . -134.15(17) ?
C5 O10 C15 C20 . . . . 46.8(2) ?
O10 C15 C16 C17 . . . . -178.90(15) ?
C20 C15 C16 C17 . . . . 0.2(3) ?
C15 C16 C17 C18 . . . . -0.2(3) ?
C16 C17 C18 C19 . . . . 0.2(3) ?
C16 C17 C18 C21 . . . . -179.67(17) ?
C17 C18 C19 C20 . . . . -0.2(3) ?
C21 C18 C19 C20 . . . . 179.63(17) ?
C18 C19 C20 C15 . . . . 0.2(3) ?
O10 C15 C20 C19 . . . . 178.82(15) ?
C16 C15 C20 C19 . . . . -0.2(3) ?
C19 C18 C21 O11 . . . . -1.9(3) ?
C17 C18 C21 O11 . . . . 177.97(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10206416
