#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227283.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_2227283
loop_
_publ_author_name
'Sacui, Iulia A.'
'Norris, Peter'
'Zeller, Matthias'
_publ_section_title
;
 2,3;5,6-Di-O-isopropylidene-1-O-(2-phenylacetyl)-α-<small>D</small>-mannofuranose
;
_journal_coeditor_code           BV2157
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2341
_journal_paper_doi               10.1107/S1600536810032368
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H26 O7'
_chemical_formula_moiety         'C20 H26 O7'
_chemical_formula_sum            'C20 H26 O7'
_chemical_formula_weight         378.41
_chemical_name_systematic
;
2,3;5,6-Di-O-isopropylidene-1-O-(2-phenylacetyl)-
α-D-mannofuranose
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6174(3)
_cell_length_b                   13.0946(8)
_cell_length_c                   25.2021(15)
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.88
_cell_volume                     1853.81(19)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18953
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.331
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0505
_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)+(0.0345P)²+1.2578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2652
_reflns_number_total             2668
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2157.cif
_cod_data_source_block           I
_cod_database_code               2227283
_cod_database_fobs_code          2227283
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_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 0.9107(3) 0.56927(14) 0.25276(7) 0.0161(4) Uani d . 1 . .
O O6 0.9344(4) 0.81639(14) 0.35444(8) 0.0199(4) Uani d . 1 . .
O O7 1.1329(3) 0.56059(15) 0.14428(7) 0.0193(4) Uani d . 1 . .
O O2 0.7450(3) 0.56285(14) 0.16757(7) 0.0167(4) Uani d . 1 . .
O O4 0.5450(4) 0.47655(14) 0.33085(7) 0.0200(4) Uani d . 1 . .
O O3 0.5940(4) 0.37204(14) 0.26113(8) 0.0230(4) Uani d . 1 . .
O O5 0.6671(3) 0.69122(14) 0.36960(7) 0.0184(4) Uani d . 1 . .
C C5 0.8432(5) 0.6452(2) 0.33622(10) 0.0166(5) Uani d . 1 . .
H H5 0.9090 0.5824 0.3534 0.020 Uiso calc R 1 . .
C C13 0.9301(5) 0.57991(19) 0.13408(10) 0.0155(5) Uani d . 1 . .
C C3 0.5230(5) 0.54195(19) 0.28614(9) 0.0140(5) Uani d . 1 . .
H H3 0.3639 0.5761 0.2846 0.017 Uiso calc R 1 . .
C C18 1.2659(6) 0.5338(2) -0.04967(10) 0.0250(6) Uani d . 1 . .
H H18 1.3616 0.5120 -0.0786 0.030 Uiso calc R 1 . .
C C17 1.0503(6) 0.4865(2) -0.03966(11) 0.0257(6) Uani d . 1 . .
H H17 0.9964 0.4330 -0.0621 0.031 Uiso calc R 1 . .
C C4 0.7276(5) 0.61858(19) 0.28397(9) 0.0147(5) Uani d . 1 . .
H H4 0.6738 0.6824 0.2657 0.018 Uiso calc R 1 . .
C C16 0.9133(5) 0.5172(2) 0.00314(11) 0.0208(6) Uani d . 1 . .
H H16 0.7668 0.4836 0.0102 0.025 Uiso calc R 1 . .
C C10 0.7721(5) 0.77973(19) 0.39329(10) 0.0167(5) Uani d . 1 . .
C C2 0.5653(5) 0.47073(19) 0.23826(10) 0.0158(5) Uani d . 1 . .
H H2 0.4323 0.4733 0.2119 0.019 Uiso calc R 1 . .
C C15 0.9879(5) 0.59677(19) 0.03595(9) 0.0162(5) Uani d . 1 . .
C C12 0.5801(6) 0.8580(2) 0.40282(12) 0.0248(6) Uani d . 1 . .
H H12A 0.6512 0.9201 0.4176 0.037 Uiso calc R 1 . .
H H12B 0.4629 0.8305 0.4278 0.037 Uiso calc R 1 . .
H H12C 0.5013 0.8743 0.3692 0.037 Uiso calc R 1 . .
C C20 1.2031(5) 0.6441(2) 0.02492(10) 0.0192(5) Uani d . 1 . .
H H20 1.2561 0.6986 0.0468 0.023 Uiso calc R 1 . .
C C8 0.2243(5) 0.3600(2) 0.31076(11) 0.0183(5) Uani d . 1 . .
H H8A 0.1581 0.3657 0.3466 0.028 Uiso calc R 1 . .
H H8B 0.1902 0.2920 0.2964 0.028 Uiso calc R 1 . .
H H8C 0.1520 0.4120 0.2879 0.028 Uiso calc R 1 . .
C C1 0.8021(4) 0.50643(19) 0.21488(9) 0.0145(5) Uani d . 1 . .
H H1 0.9061 0.4467 0.2063 0.017 Uiso calc R 1 . .
C C6 1.0386(5) 0.72767(19) 0.33117(10) 0.0178(5) Uani d . 1 . .
H H6A 1.1843 0.7072 0.3505 0.021 Uiso calc R 1 . .
H H6B 1.0795 0.7399 0.2935 0.021 Uiso calc R 1 . .
C C9 0.6133(5) 0.3004(3) 0.34852(14) 0.0324(8) Uani d . 1 . .
H H9A 0.7855 0.3125 0.3482 0.049 Uiso calc R 1 . .
H H9B 0.5804 0.2310 0.3359 0.049 Uiso calc R 1 . .
H H9C 0.5528 0.3081 0.3848 0.049 Uiso calc R 1 . .
C C19 1.3418(5) 0.6130(2) -0.01758(11) 0.0225(6) Uani d . 1 . .
H H19 1.4890 0.6461 -0.0247 0.027 Uiso calc R 1 . .
C C7 0.4927(5) 0.3763(2) 0.31284(10) 0.0176(5) Uani d . 1 . .
C C11 0.9020(6) 0.7498(2) 0.44388(11) 0.0244(6) Uani d . 1 . .
H H11A 1.0245 0.6989 0.4356 0.037 Uiso calc R 1 . .
H H11B 0.7882 0.7208 0.4692 0.037 Uiso calc R 1 . .
H H11C 0.9770 0.8104 0.4594 0.037 Uiso calc R 1 . .
C C14 0.8400(5) 0.6279(2) 0.08310(10) 0.0215(6) Uani d . 1 . .
H H14A 0.6727 0.6071 0.0772 0.026 Uiso calc R 1 . .
H H14B 0.8436 0.7032 0.0866 0.026 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 0.0033 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'
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
C1 O1 C4 . . 108.84(19) ?
C10 O6 C6 . . 105.74(19) ?
C13 O2 C1 . . 115.40(19) ?
C7 O4 C3 . . 106.61(18) ?
C7 O3 C2 . . 106.85(19) ?
C10 O5 C5 . . 107.5(2) ?
O5 C5 C4 . . 108.2(2) ?
O5 C5 C6 . . 104.2(2) ?
C4 C5 C6 . . 113.3(2) ?
O5 C5 H5 . . 110.3 ?
C4 C5 H5 . . 110.3 ?
C6 C5 H5 . . 110.3 ?
O7 C13 O2 . . 124.2(2) ?
O7 C13 C14 . . 126.0(2) ?
O2 C13 C14 . . 109.8(2) ?
O4 C3 C4 . . 111.0(2) ?
O4 C3 C2 . . 104.02(19) ?
C4 C3 C2 . . 104.7(2) ?
O4 C3 H3 . . 112.2 ?
C4 C3 H3 . . 112.2 ?
C2 C3 H3 . . 112.2 ?
C19 C18 C17 . . 120.0(3) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C17 C16 . . 119.9(3) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
O1 C4 C5 . . 105.8(2) ?
O1 C4 C3 . . 105.15(19) ?
C5 C4 C3 . . 116.4(2) ?
O1 C4 H4 . . 109.8 ?
C5 C4 H4 . . 109.8 ?
C3 C4 H4 . . 109.8 ?
C17 C16 C15 . . 120.8(3) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
O6 C10 O5 . . 104.52(19) ?
O6 C10 C12 . . 109.8(2) ?
O5 C10 C12 . . 108.8(2) ?
O6 C10 C11 . . 110.9(2) ?
O5 C10 C11 . . 109.8(2) ?
C12 C10 C11 . . 112.7(2) ?
O3 C2 C1 . . 109.6(2) ?
O3 C2 C3 . . 104.44(19) ?
C1 C2 C3 . . 104.5(2) ?
O3 C2 H2 . . 112.6 ?
C1 C2 H2 . . 112.6 ?
C3 C2 H2 . . 112.6 ?
C20 C15 C16 . . 118.5(2) ?
C20 C15 C14 . . 121.2(2) ?
C16 C15 C14 . . 120.3(3) ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C19 C20 C15 . . 121.0(3) ?
C19 C20 H20 . . 119.5 ?
C15 C20 H20 . . 119.5 ?
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 ?
O1 C1 O2 . . 111.1(2) ?
O1 C1 C2 . . 107.23(19) ?
O2 C1 C2 . . 106.4(2) ?
O1 C1 H1 . . 110.6 ?
O2 C1 H1 . . 110.6 ?
C2 C1 H1 . . 110.6 ?
O6 C6 C5 . . 104.1(2) ?
O6 C6 H6A . . 110.9 ?
C5 C6 H6A . . 110.9 ?
O6 C6 H6B . . 110.9 ?
C5 C6 H6B . . 110.9 ?
H6A C6 H6B . . 109.0 ?
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 ?
C18 C19 C20 . . 119.9(3) ?
C18 C19 H19 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
O4 C7 O3 . . 104.2(2) ?
O4 C7 C9 . . 109.1(2) ?
O3 C7 C9 . . 110.0(2) ?
O4 C7 C8 . . 110.2(2) ?
O3 C7 C8 . . 111.0(2) ?
C9 C7 C8 . . 112.0(2) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C15 C14 C13 . . 111.8(2) ?
C15 C14 H14A . . 109.3 ?
C13 C14 H14A . . 109.3 ?
C15 C14 H14B . . 109.3 ?
C13 C14 H14B . . 109.3 ?
H14A C14 H14B . . 107.9 ?
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 C1 . 1.400(3) ?
O1 C4 . 1.447(3) ?
O6 C10 . 1.421(3) ?
O6 C6 . 1.427(3) ?
O7 C13 . 1.195(3) ?
O2 C13 . 1.358(3) ?
O2 C1 . 1.439(3) ?
O4 C7 . 1.420(3) ?
O4 C3 . 1.421(3) ?
O3 C7 . 1.423(3) ?
O3 C2 . 1.424(3) ?
O5 C10 . 1.431(3) ?
O5 C5 . 1.432(3) ?
C5 C4 . 1.509(3) ?
C5 C6 . 1.545(4) ?
C5 H5 . 1.0000 ?
C13 C14 . 1.517(3) ?
C3 C4 . 1.527(4) ?
C3 C2 . 1.543(3) ?
C3 H3 . 1.0000 ?
C18 C19 . 1.382(4) ?
C18 C17 . 1.384(5) ?
C18 H18 . 0.9500 ?
C17 C16 . 1.385(4) ?
C17 H17 . 0.9500 ?
C4 H4 . 1.0000 ?
C16 C15 . 1.395(4) ?
C16 H16 . 0.9500 ?
C10 C12 . 1.507(4) ?
C10 C11 . 1.520(4) ?
C2 C1 . 1.528(3) ?
C2 H2 . 1.0000 ?
C15 C20 . 1.386(4) ?
C15 C14 . 1.506(4) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C20 C19 . 1.386(4) ?
C20 H20 . 0.9500 ?
C8 C7 . 1.523(4) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C1 H1 . 1.0000 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C9 C7 . 1.502(4) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C19 H19 . 0.9500 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
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 O6 3_745 1.00 2.46 3.382(3) 152.8
C17 H17 O5 2_664 0.95 2.54 3.483(3) 172.3
C2 H2 O7 1_455 1.00 2.65 3.591(3) 156.1
C3 H3 O1 1_455 1.00 2.67 3.559(3) 148.0
C8 H8C O1 1_455 0.98 2.62 3.570(3) 163.5
C12 H12A O7 3_755 0.98 2.70 3.323(4) 121.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656195
2 PubChem 101806962
