#------------------------------------------------------------------------------
#$Date: 2019-03-05 09:52:05 +0100 (mar 05 de mar de 2019) $
#$Revision: 213973 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/38/7103852.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_7103852
loop_
_publ_author_name
'Liu, Hong-Min'
'Zhang, Fuyi'
'Zou, Da-Peng'
_publ_section_title
;
 Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose
 via an autoxidation--Michael addition reaction
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   16
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2044
_journal_page_last               2045
_journal_paper_doi               10.1039/b306227a
_journal_year                    2003
_chemical_formula_sum            'C18 H18 N0 O9'
_chemical_formula_weight         378.32
_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                   6.3659(13)
_cell_length_b                   11.591(2)
_cell_length_c                   23.782(5)
_cell_measurement_reflns_used    180
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2
_cell_volume                     1754.8(6)
_computing_cell_refinement       raxis
_computing_data_collection       raxis
_computing_data_reduction        raxis
_computing_molecular_graphics    texsan
_computing_publication_material  texsan
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  R-axis-IV
_diffrn_measurement_method       'Osillation frames'
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5999
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_correction_T_min  0.9659
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0557
_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)+(0.0571P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                2474
_reflns_number_total             3520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306227a.txt
_cod_data_source_block           compound_7
_cod_original_sg_symbol_H-M      p2(1)2(1)2(1)
_cod_database_code               7103852
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7481(4) 0.57590(17) -0.00019(8) 0.0502(6) Uani 1 1 d . . .
O2 O 0.3673(4) 0.23197(17) 0.13605(10) 0.0633(7) Uani 1 1 d . . .
O3 O 0.3613(4) 0.42576(15) 0.13265(8) 0.0468(6) Uani 1 1 d . . .
O4 O 0.4249(3) 0.67819(15) 0.16629(8) 0.0374(5) Uani 1 1 d . . .
O5 O 0.9037(3) 0.59804(15) 0.08923(8) 0.0401(5) Uani 1 1 d . . .
O6 O 0.6697(3) 0.82983(15) 0.17125(9) 0.0490(5) Uani 1 1 d . . .
O7 O 0.8799(4) 0.2629(2) 0.01844(11) 0.0739(8) Uani 1 1 d . . .
O8 O 0.7749(4) 0.15617(16) 0.09195(9) 0.0638(7) Uani 1 1 d . . .
O9 O 0.3404(4) 0.56766(19) 0.06555(9) 0.0645(7) Uani 1 1 d . . .
H9A H 0.2472 0.6017 0.0826 0.097 Uiso 1 1 calc R . .
C1 C 0.8268(5) 0.5189(2) 0.04691(11) 0.0401(7) Uani 1 1 d . . .
H1A H 0.9391 0.4659 0.0357 0.048 Uiso 1 1 calc R . .
C2 C 0.6483(5) 0.4520(2) 0.07313(10) 0.0339(6) Uani 1 1 d . . .
C3 C 0.4760(5) 0.5152(2) 0.10395(11) 0.0346(7) Uani 1 1 d . . .
C4 C 0.5782(5) 0.6008(2) 0.14384(11) 0.0331(6) Uani 1 1 d . . .
H4A H 0.6476 0.5592 0.1745 0.040 Uiso 1 1 calc R . .
C5 C 0.7403(4) 0.6713(2) 0.11102(12) 0.0355(6) Uani 1 1 d . . .
H5A H 0.6707 0.7112 0.0798 0.043 Uiso 1 1 calc R . .
C6 C 0.8379(5) 0.7595(2) 0.15032(14) 0.0493(8) Uani 1 1 d . . .
H6A H 0.9091 0.7211 0.1811 0.059 Uiso 1 1 calc R . .
H6B H 0.9392 0.8065 0.1303 0.059 Uiso 1 1 calc R . .
C7 C 0.9043(8) 0.6204(4) -0.03551(17) 0.0984(17) Uani 1 1 d . . .
H7A H 0.8399 0.6593 -0.0667 0.148 Uiso 1 1 calc R . .
H7B H 0.9905 0.5585 -0.0492 0.148 Uiso 1 1 calc R . .
H7C H 0.9896 0.6740 -0.0149 0.148 Uiso 1 1 calc R . .
C8 C 0.6288(5) 0.3394(2) 0.08188(12) 0.0398(7) Uani 1 1 d . . .
C9 C 0.7755(5) 0.2489(2) 0.06038(14) 0.0463(8) Uani 1 1 d . . .
C10 C 0.9248(7) 0.0667(3) 0.07572(17) 0.0823(13) Uani 1 1 d . . .
H10A H 0.9127 0.0024 0.1010 0.123 Uiso 1 1 calc R . .
H10B H 1.0649 0.0972 0.0775 0.123 Uiso 1 1 calc R . .
H10C H 0.8954 0.0417 0.0380 0.123 Uiso 1 1 calc R . .
C11 C 0.5244(5) 0.7642(3) 0.20228(12) 0.0418(7) Uani 1 1 d . . .
H11A H 0.5957 0.7260 0.2337 0.050 Uiso 1 1 calc R . .
C12 C 0.3503(5) 0.8399(2) 0.22420(11) 0.0404(7) Uani 1 1 d . . .
C13 C 0.2227(6) 0.7980(2) 0.26679(12) 0.0484(8) Uani 1 1 d . . .
H13A H 0.2526 0.7266 0.2828 0.058 Uiso 1 1 calc R . .
C14 C 0.0533(6) 0.8597(3) 0.28567(14) 0.0545(9) Uani 1 1 d . . .
H14A H -0.0323 0.8296 0.3138 0.065 Uiso 1 1 calc R . .
C15 C 0.0092(6) 0.9675(3) 0.26281(14) 0.0535(9) Uani 1 1 d . . .
H15A H -0.1053 1.0100 0.2755 0.064 Uiso 1 1 calc R . .
C16 C 0.1368(6) 1.0104(3) 0.22130(13) 0.0522(9) Uani 1 1 d . . .
H16A H 0.1081 1.0824 0.2059 0.063 Uiso 1 1 calc R . .
C17 C 0.3076(5) 0.9480(2) 0.20198(12) 0.0447(8) Uani 1 1 d . . .
H17A H 0.3936 0.9786 0.1741 0.054 Uiso 1 1 calc R . .
C18 C 0.4429(5) 0.3191(2) 0.11896(13) 0.0449(8) Uani 1 1 d . . .
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 113.7(3) . . ?
C18 O3 C3 110.0(2) . . ?
C4 O4 C11 110.6(2) . . ?
C5 O5 C1 112.3(2) . . ?
C11 O6 C6 111.4(2) . . ?
C9 O8 C10 115.4(3) . . ?
O1 C1 O5 112.3(2) . . ?
O1 C1 C2 107.7(3) . . ?
O5 C1 C2 107.0(2) . . ?
C8 C2 C3 109.5(3) . . ?
C8 C2 C1 129.8(3) . . ?
C3 C2 C1 119.9(2) . . ?
O9 C3 O3 108.1(2) . . ?
O9 C3 C2 110.1(2) . . ?
O3 C3 C2 104.4(2) . . ?
O9 C3 C4 112.9(2) . . ?
O3 C3 C4 113.0(2) . . ?
C2 C3 C4 108.0(2) . . ?
O4 C4 C3 110.6(2) . . ?
O4 C4 C5 108.39(19) . . ?
C3 C4 C5 108.6(2) . . ?
O5 C5 C6 108.8(2) . . ?
O5 C5 C4 110.8(2) . . ?
C6 C5 C4 108.8(2) . . ?
O6 C6 C5 106.9(2) . . ?
C2 C8 C18 108.8(2) . . ?
C2 C8 C9 125.3(3) . . ?
C18 C8 C9 125.9(2) . . ?
O7 C9 O8 125.7(3) . . ?
O7 C9 C8 122.1(3) . . ?
O8 C9 C8 112.2(3) . . ?
O6 C11 O4 110.3(2) . . ?
O6 C11 C12 110.5(2) . . ?
O4 C11 C12 106.4(2) . . ?
C17 C12 C13 118.7(3) . . ?
C17 C12 C11 122.6(3) . . ?
C13 C12 C11 118.6(3) . . ?
C14 C13 C12 121.1(3) . . ?
C13 C14 C15 120.0(3) . . ?
C16 C15 C14 119.1(3) . . ?
C15 C16 C17 121.0(3) . . ?
C16 C17 C12 120.0(3) . . ?
O2 C18 O3 121.8(3) . . ?
O2 C18 C8 130.9(3) . . ?
O3 C18 C8 107.2(2) . . ?
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
O1 C1 1.394(3) . ?
O1 C7 1.400(5) . ?
O2 C18 1.190(3) . ?
O3 C18 1.380(3) . ?
O3 C3 1.440(3) . ?
O4 C4 1.429(3) . ?
O4 C11 1.458(3) . ?
O5 C5 1.439(3) . ?
O5 C1 1.447(3) . ?
O6 C11 1.407(3) . ?
O6 C6 1.435(4) . ?
O7 C9 1.210(4) . ?
O8 C9 1.311(4) . ?
O8 C10 1.462(4) . ?
O9 C3 1.396(3) . ?
C1 C2 1.510(4) . ?
C2 C8 1.327(4) . ?
C2 C3 1.509(4) . ?
C3 C4 1.519(4) . ?
C4 C5 1.531(4) . ?
C5 C6 1.518(4) . ?
C8 C18 1.495(4) . ?
C8 C9 1.495(4) . ?
C11 C12 1.507(4) . ?
C12 C17 1.386(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.370(5) . ?
C14 C15 1.391(5) . ?
C15 C16 1.371(5) . ?
C16 C17 1.384(4) . ?
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
C7 O1 C1 O5 75.7(4) . . . . ?
C7 O1 C1 C2 -166.7(3) . . . . ?
C5 O5 C1 O1 62.5(3) . . . . ?
C5 O5 C1 C2 -55.5(3) . . . . ?
O1 C1 C2 C8 119.8(3) . . . . ?
O5 C1 C2 C8 -119.2(3) . . . . ?
O1 C1 C2 C3 -72.2(3) . . . . ?
O5 C1 C2 C3 48.8(3) . . . . ?
C18 O3 C3 O9 113.9(3) . . . . ?
C18 O3 C3 C2 -3.2(3) . . . . ?
C18 O3 C3 C4 -120.4(3) . . . . ?
C8 C2 C3 O9 -113.9(3) . . . . ?
C1 C2 C3 O9 75.8(3) . . . . ?
C8 C2 C3 O3 1.9(3) . . . . ?
C1 C2 C3 O3 -168.4(2) . . . . ?
C8 C2 C3 C4 122.4(3) . . . . ?
C1 C2 C3 C4 -47.8(3) . . . . ?
C11 O4 C4 C3 -177.0(2) . . . . ?
C11 O4 C4 C5 -58.1(3) . . . . ?
O9 C3 C4 O4 47.1(3) . . . . ?
O3 C3 C4 O4 -76.0(3) . . . . ?
C2 C3 C4 O4 169.0(2) . . . . ?
O9 C3 C4 C5 -71.7(3) . . . . ?
O3 C3 C4 C5 165.2(2) . . . . ?
C2 C3 C4 C5 50.2(3) . . . . ?
C1 O5 C5 C6 -174.1(2) . . . . ?
C1 O5 C5 C4 66.3(3) . . . . ?
O4 C4 C5 O5 177.7(2) . . . . ?
C3 C4 C5 O5 -62.1(3) . . . . ?
O4 C4 C5 C6 58.1(3) . . . . ?
C3 C4 C5 C6 178.2(2) . . . . ?
C11 O6 C6 C5 62.1(3) . . . . ?
O5 C5 C6 O6 -179.6(2) . . . . ?
C4 C5 C6 O6 -58.7(3) . . . . ?
C3 C2 C8 C18 0.1(3) . . . . ?
C1 C2 C8 C18 169.1(3) . . . . ?
C3 C2 C8 C9 -177.2(3) . . . . ?
C1 C2 C8 C9 -8.2(5) . . . . ?
C10 O8 C9 O7 4.0(5) . . . . ?
C10 O8 C9 C8 -176.1(3) . . . . ?
C2 C8 C9 O7 -26.3(5) . . . . ?
C18 C8 C9 O7 156.9(3) . . . . ?
C2 C8 C9 O8 153.8(3) . . . . ?
C18 C8 C9 O8 -23.0(4) . . . . ?
C6 O6 C11 O4 -63.1(3) . . . . ?
C6 O6 C11 C12 179.6(2) . . . . ?
C4 O4 C11 O6 60.9(3) . . . . ?
C4 O4 C11 C12 -179.3(2) . . . . ?
O6 C11 C12 C17 18.6(4) . . . . ?
O4 C11 C12 C17 -101.2(3) . . . . ?
O6 C11 C12 C13 -164.0(3) . . . . ?
O4 C11 C12 C13 76.2(3) . . . . ?
C17 C12 C13 C14 2.0(4) . . . . ?
C11 C12 C13 C14 -175.5(3) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C16 C17 C12 0.7(5) . . . . ?
C13 C12 C17 C16 -1.8(4) . . . . ?
C11 C12 C17 C16 175.6(3) . . . . ?
C3 O3 C18 O2 -176.9(3) . . . . ?
C3 O3 C18 C8 3.3(3) . . . . ?
C2 C8 C18 O2 178.2(4) . . . . ?
C9 C8 C18 O2 -4.6(6) . . . . ?
C2 C8 C18 O3 -2.1(3) . . . . ?
C9 C8 C18 O3 175.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10181505
