[1,4]-sigmatropic rearrangement of chiral nitrones and their utilization in the synthesis of new iminosugars.
Malinowski, Maciej; Rowicki, Tomasz; Guzik, Patrycja; Gryszel, Maciej; Łapczyński, Sebastian; Wielechowska, Monika; Czerwińska, Karolina; Madura, Izabela; Sas, Wojciech; Organic & biomolecular chemistry 14 (2015) 470–482; doi:10.1039/c5ob01432h

data_7154801
_publ_section_title
;
 [1,4]-sigmatropic rearrangement of chiral nitrones and their utilization
 in the synthesis of new iminosugars.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              470
_journal_page_last               482
_journal_paper_doi               10.1039/c5ob01432h
_journal_volume                  14
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H20 N O3, Cl'
_chemical_formula_sum            'C10 H20 Cl N O3'
_chemical_formula_weight         237.72
_chemical_name_systematic
'(1S,2R,7S,8aS)-1,2,7-trihydroxy-5,5-dimethyloctahydro-1H-indolizin-4-ium chloride'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_audit_update_record
;
2015-10-15 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.82581(5)
_cell_length_b                   12.02340(7)
_cell_length_c                   14.64680(9)
_cell_measurement_reflns_used    26693
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      67.0640
_cell_measurement_theta_min      4.7140
_cell_volume                     1202.055(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   12.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   57.0000   60.0000 103

  2 omega    7.00  120.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   77.0000 -180.0000 113

  3 omega   48.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363  161.0000  152.0000 73

  4 omega   -5.00  123.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   19.0000    0.0000 128

  5 omega  -10.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363 -117.0000  -85.0000 102

  6 omega   12.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   57.0000  120.0000 103

  7 omega   16.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000  -11.3822 113

  8 omega   16.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000  -70.7882 113

  9 omega   20.00  133.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -147.0319 113

 10 omega   20.00  133.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   22.5443 113

 11 omega   20.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000   51.4205 114

 12 omega   24.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000   63.5892 114

 13 omega   24.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000 -178.7908 114

 14 omega   28.00  142.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000  100.6025 114

 15 omega   32.00  145.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000   73.3947 113

 16 omega   32.00  146.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  133.3587 114

 17 omega   34.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  164.4682 26

 18 omega   36.00   61.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   79.0000  -83.3355 25

 19 omega   36.00   62.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   78.0000  -48.1603 26

 20 omega   41.00   67.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   78.0000 -107.2474 26

 21 omega   41.00   72.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   79.0000  -23.2225 31

 22 omega  -85.00  -53.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -62.0000  -18.4345 32

 23 omega  -81.00  -53.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000   24.7890 28

 24 omega  -76.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 26

 25 omega  -80.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000   36.1809 30

 26 omega  -75.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 26

 27 omega  -75.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  168.8117 26

 28 omega  -78.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -73.0000 -171.7670 27

 29 omega  -76.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -60.0000 26

 30 omega  -75.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 26

 31 omega  -77.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -73.0000   64.2323 26

 32 omega  -77.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 26

 33 omega  -91.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 42

 34 omega  -85.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 36

 35 omega  -76.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 26

 36 omega  -77.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 26

 37 omega   60.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 34

 38 omega   85.00  135.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 50

 39 omega   60.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 37

 40 omega   60.00  147.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 87

 41 omega   21.00   46.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -180.0000 25

 42 omega  123.00  160.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 37

 43 omega   86.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -67.0000 -121.6956 34

 44 omega   33.00   65.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 32

 45 omega   33.00   59.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -67.0000 -121.6956 26

 46 omega  131.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 26

 47 omega   80.00  123.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000 -113.2332 43

 48 omega   91.00  119.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 28

 49 omega   78.00  127.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 49

 50 omega   97.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 74

 51 omega   62.00  123.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -180.0000 61

 52 omega    9.00   50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000 -113.2332 41

 53 omega   64.00   93.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 29

 54 omega   12.00  133.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   23.7007 121

 55 omega   27.00   52.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 25

 56 omega   87.00  121.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 34

 57 omega   93.00  145.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 52

 58 omega   60.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 29

 59 omega   61.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -177.1363 48

 60 omega   25.00   76.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 51

 61 omega  129.00  164.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 35

 62 omega   29.00   58.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -177.1363 29

 63 omega   88.00  147.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  150.0000 59

 64 omega   18.00   47.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  150.0000 29

 65 omega   74.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 35

 66 omega   61.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 110

 67 omega   63.00  143.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 80

 68 omega   21.00   80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 59

 69 omega   62.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 82

 70 omega   61.00  124.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 63

 71 omega  147.00  172.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 25

 72 omega   60.00  100.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 40

 73 omega  139.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -30.0000 32

 74 omega   63.00  123.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 60

 75 omega   87.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -30.0000 26

 76 omega  108.00  154.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -90.0000 46

 77 omega  114.00  140.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 26

 78 omega  139.00  172.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 33

 79 omega   63.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 34

 80 omega  137.00  163.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0019839000
_diffrn_orient_matrix_UB_12      0.0867686000
_diffrn_orient_matrix_UB_13      -0.0773765000
_diffrn_orient_matrix_UB_21      -0.0490001000
_diffrn_orient_matrix_UB_22      0.0918345000
_diffrn_orient_matrix_UB_23      0.0696515000
_diffrn_orient_matrix_UB_31      0.2203567000
_diffrn_orient_matrix_UB_32      0.0212259000
_diffrn_orient_matrix_UB_33      0.0149198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33361
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         67.168
_diffrn_reflns_theta_min         4.758
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(3)
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0217
_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^)+(0.0360P)^2^+0.3460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0580
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2128
_reflns_number_total             2148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01432h2.cif
_cod_data_source_block           15a
_cod_depositor_comments
'Adding full bibliography for 7154801--7154802.cif.'
_cod_original_cell_volume        1202.054(14)
_cod_database_code               7154801
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1b), C2(H2a), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C6(H6a,H6b), C8(H8a,H8b)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_shelx_res_checksum              58127