Short synthesis, X-ray and conformational analysis of a cyclic peracetylated l-sorbose-derived nitrone, a useful intermediate towards N–O-containing d-gluco-iminosugars
Tangara, Salia; Kanazawa, Alice; Fayolle, Martine; Philouze, Christian; Poisson, Jean-François; Behr, Jean-Bernard; Py, Sandrine; New Journal of Chemistry 42 (2018) 16735–; doi:10.1039/C8NJ03868F

data_7057744
_publ_section_title
;
 Short synthesis, X-ray and conformational analysis of a cyclic
 peracetylated l-sorbose-derived nitrone, a useful intermediate towards
 N--O-containing d-gluco-iminosugars
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16735
_journal_paper_doi               10.1039/C8NJ03868F
_journal_volume                  42
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H19 N O9'
_chemical_formula_sum            'C14 H19 N O9'
_chemical_formula_weight         345.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2017-11-27 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.91(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8584(18)
_cell_length_b                   7.6373(15)
_cell_length_c                   12.517(3)
_cell_measurement_reflns_used    19394
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.000
_cell_measurement_theta_min      3.638
_cell_volume                     822.0(3)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker kappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19394
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.975
_diffrn_reflns_theta_min         3.638
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Mo
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0805 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8732.
The \l/2 correction factor is 0.0000.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 1239 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0977P)^2^+1.2107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1812
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                2838
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj03868f2.cif
_cod_data_source_block           sad
_cod_depositor_comments          'Adding full bibliography for 7057744.cif.'
_cod_database_code               7057744
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              30135
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'