#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/11/2221154.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_2221154
loop_
_publ_author_name
'Burkhardt, Anja'
'Eriksson, Lars'
'Widmalm, Göran'
'Cumpstey, Ian'
_publ_section_title
;(Z)-1,2:5,6-Di-O-isopropylidene-α-<small>D</small>-ribo-hexofuranos-3-ulose
 O-benzyloxime
;
_journal_coeditor_code           NG2545
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o633
_journal_paper_doi               10.1107/S1600536809006333
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H25 N O6'
_chemical_formula_moiety         'C19 H25 N O6'
_chemical_formula_sum            'C19 H25 N O6'
_chemical_formula_weight         363.40
_chemical_melting_point          403.0(10)
_chemical_name_systematic
;
(Z)-1,2:5,6-Di-O-isopropylidene-α-D-ribo-
hexofuranos-3-ulose O-benzyloxime
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.122(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8012(12)
_cell_length_b                   6.0019(5)
_cell_length_c                   13.7021(11)
_cell_measurement_reflns_used    1353
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      1.9
_cell_volume                     966.64(15)
_computing_cell_refinement
'CELL in IPDS Software (Stoe & Cie, 1997)'
_computing_data_collection
'EXPOSE in IPDS Software (Stoe & Cie, 1997)'
_computing_data_reduction
'INTEGRATE in IPDS Software (Stoe & Cie, 1997)'
_computing_molecular_graphics    'XP (Siemens, 1990)'
_computing_publication_material
'PLATON (Spek, 2009), XP (Siemens, 1990) and SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       φ
_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  0.1038
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9449
_diffrn_reflns_theta_full        28.21
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0522
_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)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                2023
_reflns_number_total             2558
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2545.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2221154
_cod_database_fobs_code          2221154
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
N N1 -0.06053(17) 0.2232(4) 0.27810(14) 0.0389(4) Uani d . 1 . .
O O1 0.02900(13) 0.5554(3) 0.09073(11) 0.0389(4) Uani d . 1 . .
O O2 0.11981(15) 0.8375(3) 0.18283(13) 0.0445(4) Uani d . 1 . .
O O3 0.07981(16) 0.6561(4) 0.32044(12) 0.0510(5) Uani d . 1 . .
O O4 -0.06093(18) 0.2884(3) 0.37689(13) 0.0477(4) Uani d . 1 . .
O O5 -0.21517(14) 0.5609(3) 0.09506(14) 0.0469(4) Uani d . 1 . .
O O6 -0.34050(19) 0.2785(5) 0.0706(3) 0.1008(12) Uani d . 1 . .
C C1 0.01554(19) 0.7319(4) 0.15833(17) 0.0371(5) Uani d . 1 . .
H H1 -0.0423 0.8385 0.1321 0.044 Uiso calc R 1 . .
C C2 -0.01695(19) 0.6276(4) 0.25278(17) 0.0363(5) Uani d . 1 . .
H H2 -0.0841 0.7001 0.2758 0.044 Uiso calc R 1 . .
C C3 -0.04108(17) 0.3891(4) 0.22521(16) 0.0325(4) Uani d . 1 . .
C C4 -0.03742(18) 0.3679(4) 0.11580(16) 0.0334(4) Uani d . 1 . .
H H4 0.0012 0.2294 0.1004 0.040 Uiso calc R 1 . .
C C5 -0.15390(19) 0.3778(4) 0.05929(18) 0.0384(5) Uani d . 1 . .
H H5 -0.1455 0.3985 -0.0106 0.046 Uiso calc R 1 . .
C C6 -0.2320(2) 0.1834(5) 0.0731(3) 0.0554(7) Uani d . 1 . .
H H6A -0.2283 0.0754 0.0208 0.067 Uiso calc R 1 . .
H H6B -0.2119 0.1103 0.1354 0.067 Uiso calc R 1 . .
C C7 0.1722(2) 0.7382(5) 0.27004(19) 0.0457(6) Uani d . 1 . .
C C8 0.2295(3) 0.9206(6) 0.3320(3) 0.0664(9) Uani d . 1 . .
H H8A 0.2656 0.8576 0.3913 0.100 Uiso calc R 1 . .
H H8B 0.1738 1.0280 0.3479 0.100 Uiso calc R 1 . .
H H8C 0.2857 0.9922 0.2963 0.100 Uiso calc R 1 . .
C C9 0.2493(3) 0.5495(8) 0.2465(3) 0.0773(10) Uani d . 1 . .
H H9A 0.2837 0.4860 0.3063 0.116 Uiso calc R 1 . .
H H9B 0.3076 0.6048 0.2084 0.116 Uiso calc R 1 . .
H H9C 0.2058 0.4375 0.2099 0.116 Uiso calc R 1 . .
C C10 -0.0865(2) 0.0973(5) 0.43327(18) 0.0494(6) Uani d . 1 . .
H H10A -0.0655 0.1285 0.5020 0.059 Uiso calc R 1 . .
H H10B -0.0403 -0.0266 0.4146 0.059 Uiso calc R 1 . .
C C11 -0.2096(2) 0.0296(5) 0.42074(18) 0.0452(6) Uani d . 1 . .
C C12 -0.2392(3) -0.1738(7) 0.4566(4) 0.0787(12) Uani d . 1 . .
H H12 -0.1830 -0.2674 0.4856 0.094 Uiso calc R 1 . .
C C13 -0.3520(3) -0.2411(8) 0.4502(4) 0.0966(15) Uani d . 1 . .
H H13 -0.3711 -0.3789 0.4751 0.116 Uiso calc R 1 . .
C C14 -0.4337(3) -0.1078(10) 0.4081(4) 0.0921(14) Uani d . 1 . .
H H14 -0.5095 -0.1515 0.4058 0.111 Uiso calc R 1 . .
C C15 -0.4060(3) 0.0900(11) 0.3690(5) 0.114(2) Uani d . 1 . .
H H15 -0.4623 0.1795 0.3376 0.137 Uiso calc R 1 . .
C C16 -0.2925(3) 0.1590(7) 0.3761(3) 0.0835(12) Uani d . 1 . .
H H16 -0.2738 0.2956 0.3498 0.100 Uiso calc R 1 . .
C C17 -0.3326(2) 0.5127(6) 0.0709(3) 0.0613(8) Uani d . 1 . .
C C18 -0.3984(3) 0.6133(11) 0.1487(4) 0.1084(18) Uani d . 1 . .
H H18A -0.3931 0.7728 0.1458 0.163 Uiso calc R 1 . .
H H18B -0.3674 0.5623 0.2119 0.163 Uiso calc R 1 . .
H H18C -0.4767 0.5693 0.1380 0.163 Uiso calc R 1 . .
C C19 -0.3701(3) 0.5986(8) -0.0303(3) 0.0872(12) Uani d . 1 . .
H H19A -0.3649 0.7582 -0.0307 0.131 Uiso calc R 1 . .
H H19B -0.4473 0.5545 -0.0481 0.131 Uiso calc R 1 . .
H H19C -0.3218 0.5378 -0.0765 0.131 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 O4 . . 110.36(19) ?
C1 O1 C4 . . 109.48(16) ?
C1 O2 C7 . . 108.55(18) ?
C2 O3 C7 . . 109.31(17) ?
N1 O4 C10 . . 108.36(18) ?
C17 O5 C5 . . 106.0(2) ?
C6 O6 C17 . . 110.3(2) ?
O2 C1 O1 . . 110.25(18) ?
O2 C1 C2 . . 105.44(18) ?
O1 C1 C2 . . 107.37(19) ?
O2 C1 H1 . . 111.2 ?
O1 C1 H1 . . 111.2 ?
C2 C1 H1 . . 111.2 ?
O3 C2 C3 . . 113.8(2) ?
O3 C2 C1 . . 104.96(18) ?
C3 C2 C1 . . 103.64(19) ?
O3 C2 H2 . . 111.3 ?
C3 C2 H2 . . 111.3 ?
C1 C2 H2 . . 111.3 ?
N1 C3 C2 . . 130.3(2) ?
N1 C3 C4 . . 121.7(2) ?
C2 C3 C4 . . 107.98(19) ?
O1 C4 C3 . . 103.72(17) ?
O1 C4 C5 . . 109.72(18) ?
C3 C4 C5 . . 113.50(18) ?
O1 C4 H4 . . 109.9 ?
C3 C4 H4 . . 109.9 ?
C5 C4 H4 . . 109.9 ?
O5 C5 C6 . . 102.63(19) ?
O5 C5 C4 . . 108.59(18) ?
C6 C5 C4 . . 116.2(2) ?
O5 C5 H5 . . 109.7 ?
C6 C5 H5 . . 109.7 ?
C4 C5 H5 . . 109.7 ?
O6 C6 C5 . . 104.4(2) ?
O6 C6 H6A . . 110.9 ?
C5 C6 H6A . . 110.9 ?
O6 C6 H6B . . 110.9 ?
C5 C6 H6B . . 110.9 ?
H6A C6 H6B . . 108.9 ?
O2 C7 O3 . . 104.90(19) ?
O2 C7 C9 . . 111.1(3) ?
O3 C7 C9 . . 110.2(3) ?
O2 C7 C8 . . 107.9(2) ?
O3 C7 C8 . . 107.6(2) ?
C9 C7 C8 . . 114.6(3) ?
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 ?
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 ?
O4 C10 C11 . . 113.8(2) ?
O4 C10 H10A . . 108.8 ?
C11 C10 H10A . . 108.8 ?
O4 C10 H10B . . 108.8 ?
C11 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
C16 C11 C12 . . 118.4(3) ?
C16 C11 C10 . . 123.3(3) ?
C12 C11 C10 . . 118.3(3) ?
C11 C12 C13 . . 120.6(4) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C14 C13 C12 . . 120.2(4) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.2(4) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C16 . . 119.8(4) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C11 C16 C15 . . 120.8(4) ?
C11 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
O6 C17 O5 . . 105.4(2) ?
O6 C17 C18 . . 111.4(4) ?
O5 C17 C18 . . 107.9(3) ?
O6 C17 C19 . . 109.0(4) ?
O5 C17 C19 . . 110.1(3) ?
C18 C17 C19 . . 112.8(3) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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
N1 C3 . 1.265(3) ?
N1 O4 . 1.410(3) ?
O1 C1 . 1.425(3) ?
O1 C4 . 1.431(3) ?
O2 C1 . 1.398(3) ?
O2 C7 . 1.426(3) ?
O3 C2 . 1.416(3) ?
O3 C7 . 1.429(3) ?
O4 C10 . 1.430(3) ?
O5 C17 . 1.426(3) ?
O5 C5 . 1.426(3) ?
O6 C6 . 1.400(4) ?
O6 C17 . 1.409(4) ?
C1 C2 . 1.518(3) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.501(3) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.509(3) ?
C4 C5 . 1.517(3) ?
C4 H4 . 0.9800 ?
C5 C6 . 1.509(4) ?
C5 H5 . 0.9800 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C9 . 1.506(5) ?
C7 C8 . 1.508(4) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.504(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.352(4) ?
C11 C12 . 1.373(5) ?
C12 C13 . 1.386(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.343(7) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.354(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.397(6) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C18 . 1.501(6) ?
C17 C19 . 1.508(5) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
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
C5 H5 O2 . . 2_545 0.98 2.43 3.386(3) 164 yes
C10 H10A O3 . . 2_546 0.97 2.46 3.387(3) 160 yes
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
C3 N1 O4 C10 . . . . 178.3(2) ?
C7 O2 C1 O1 . . . . -93.8(2) ?
C7 O2 C1 C2 . . . . 21.8(3) ?
C4 O1 C1 O2 . . . . 139.51(18) ?
C4 O1 C1 C2 . . . . 25.1(2) ?
C7 O3 C2 C3 . . . . 104.1(2) ?
C7 O3 C2 C1 . . . . -8.6(3) ?
O2 C1 C2 O3 . . . . -8.0(3) ?
O1 C1 C2 O3 . . . . 109.5(2) ?
O2 C1 C2 C3 . . . . -127.70(19) ?
O1 C1 C2 C3 . . . . -10.1(2) ?
O4 N1 C3 C2 . . . . 1.8(3) ?
O4 N1 C3 C4 . . . . -179.14(19) ?
O3 C2 C3 N1 . . . . 58.5(3) ?
C1 C2 C3 N1 . . . . 172.0(2) ?
O3 C2 C3 C4 . . . . -120.6(2) ?
C1 C2 C3 C4 . . . . -7.2(2) ?
C1 O1 C4 C3 . . . . -28.9(2) ?
C1 O1 C4 C5 . . . . 92.7(2) ?
N1 C3 C4 O1 . . . . -157.54(19) ?
C2 C3 C4 O1 . . . . 21.7(2) ?
N1 C3 C4 C5 . . . . 83.5(3) ?
C2 C3 C4 C5 . . . . -97.3(2) ?
C17 O5 C5 C6 . . . . -33.8(3) ?
C17 O5 C5 C4 . . . . -157.3(2) ?
O1 C4 C5 O5 . . . . -68.6(2) ?
C3 C4 C5 O5 . . . . 46.9(3) ?
O1 C4 C5 C6 . . . . 176.4(2) ?
C3 C4 C5 C6 . . . . -68.1(3) ?
C17 O6 C6 C5 . . . . -8.4(4) ?
O5 C5 C6 O6 . . . . 25.7(3) ?
C4 C5 C6 O6 . . . . 144.0(3) ?
C1 O2 C7 O3 . . . . -27.2(3) ?
C1 O2 C7 C9 . . . . 91.9(3) ?
C1 O2 C7 C8 . . . . -141.6(2) ?
C2 O3 C7 O2 . . . . 21.7(3) ?
C2 O3 C7 C9 . . . . -98.0(3) ?
C2 O3 C7 C8 . . . . 136.4(2) ?
N1 O4 C10 C11 . . . . -74.9(3) ?
O4 C10 C11 C16 . . . . -12.1(4) ?
O4 C10 C11 C12 . . . . 168.0(3) ?
C16 C11 C12 C13 . . . . -2.2(7) ?
C10 C11 C12 C13 . . . . 177.7(4) ?
C11 C12 C13 C14 . . . . 0.4(8) ?
C12 C13 C14 C15 . . . . 2.0(9) ?
C13 C14 C15 C16 . . . . -2.5(9) ?
C12 C11 C16 C15 . . . . 1.7(7) ?
C10 C11 C16 C15 . . . . -178.2(5) ?
C14 C15 C16 C11 . . . . 0.6(9) ?
C6 O6 C17 O5 . . . . -12.4(5) ?
C6 O6 C17 C18 . . . . -129.1(4) ?
C6 O6 C17 C19 . . . . 105.8(4) ?
C5 O5 C17 O6 . . . . 29.4(4) ?
C5 O5 C17 C18 . . . . 148.5(3) ?
C5 O5 C17 C19 . . . . -88.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000931
