Regio- and stereoselective (3 + 2)-cycloaddition reactions of nitrones with cyclic allenes.
Efremova, Mariia M.; Makarova, Anastasia A.; Novikov, Alexander S.; Kryukova, Mariya A.; Kuznetsov, Mikhail A.; Molchanov, Alexander P.; Organic & biomolecular chemistry 19 (2021) 9773–9784; doi:10.1039/d1ob01584b

data_7158357
_publ_section_title
;
 Regio- and stereoselective (3 + 2)-cycloaddition reactions of nitrones
 with cyclic allenes.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9773
_journal_page_last               9784
_journal_paper_doi               10.1039/d1ob01584b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H23 N O5'
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_weight         357.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-21 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.32060(10)
_cell_length_b                   10.38740(10)
_cell_length_c                   20.71850(10)
_cell_measurement_reflns_used    28991
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.2450
_cell_measurement_theta_min      2.1500
_cell_volume                     1790.69(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -59.00  25.00   0.50    0.20    --  -38.82  86.00  41.00  168
  2  \w     12.00  44.00   0.50    0.20    --   38.82 -86.00 -76.00   64
  3  \w    120.00 146.00   0.50    0.20    --  100.00  86.00  41.00   52
  4  \w    102.00 128.00   0.50    0.20    --  100.00 -86.00 -76.00   52
  5  \w    -61.00 -18.00   0.50    0.20    --    0.00 142.00 150.06   86
  6  \w    -47.00 -22.00   0.50    0.20    --   24.00 158.00-106.07   50
  7  \w    -42.00 -17.00   0.50    0.20    --   24.00 149.00  64.13   50
  8  \w     -7.00  18.00   0.50    0.20    --   28.00  98.00-107.08   50
  9  \w      0.00  25.00   0.50    0.20    --   32.00  90.00 149.36   50
 10  \w      0.00  25.00   0.50    0.20    --   32.00  91.00  -0.47   50
 11  \w     -1.00  24.00   0.50    0.20    --   32.00  93.00-161.37   50
 12  \w     -1.00  24.00   0.50    0.20    --   32.00  94.00  31.45   50
 13  \w      6.00  31.00   0.50    0.20    --   36.00  87.00 139.17   50
 14  \w      5.00  30.00   0.50    0.20    --   36.00  89.00-157.69   50
 15  \w      6.00  31.00   0.50    0.20    --   36.00  86.00 173.24   50
 16  \w      4.00  29.00   0.50    0.20    --   36.00  90.00 -41.93   50
 17  \w      4.00  29.00   0.50    0.20    --   36.00  90.00  69.13   50
 18  \w      6.00  31.00   0.50    0.20    --   36.00  88.00-127.81   50
 19  \w    -88.00 -32.00   0.50    0.20    --  -38.82 138.00 -60.00  112
 20  \w    -62.00  24.00   0.50    0.20    --  -38.82  65.00 -90.00  172
 21  \w     17.00  85.00   0.50    0.20    --   38.82-138.00  30.00  136
 22  \w      9.00  34.00   0.50    0.20    --   38.82  85.00  88.79   50
 23  \w    -27.00  66.00   0.50    0.20    --   38.82 -77.00  90.00  186
 24  \w     38.00  93.00   0.50    0.20    --   38.82-138.00-120.00  110
 25  \w     26.00  75.00   0.50    0.20    --   38.82-104.00-180.00   98
 26  \w     11.00  36.00   0.50    0.20    --   40.00  84.00-179.77   50
 27  \w     11.00  36.00   0.50    0.20    --   40.00  84.00-161.47   50
 28  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 103.90   50
 29  \w     16.00  41.00   0.50    0.20    --   44.00  81.00   5.99   50
 30  \w     17.00  42.00   0.50    0.20    --   44.00  79.00 -85.50   50
 31  \w     16.00  41.00   0.50    0.20    --   44.00  82.00-149.94   50
 32  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 -72.60   50
 33  \w     16.00  41.00   0.50    0.20    --   44.00  81.00-174.73   50
 34  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 -19.20   50
 35  \w     16.00  41.00   0.50    0.20    --   44.00  82.00  41.48   50
 36  \w     20.00  45.00   0.50    0.20    --   44.00  80.00-130.48   50
 37  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 141.06   50
 38  \w     19.00  45.00   0.50    0.20    --   44.00  80.00  21.66   52
 39  \w     17.00  42.00   0.50    0.20    --   44.00  79.00  97.53   50
 40  \w     16.00  41.00   0.50    0.20    --   44.00  81.00  56.88   50
 41  \w     27.00  70.00   0.50    0.20    --   52.00  75.00 -47.79   86
 42  \w     31.00  57.00   0.50    0.20    --   56.00  76.00 151.27   52
 43  \w     29.00  64.00   0.50    0.20    --   56.00  77.00-152.42   70
 44  \w     90.00 124.00   0.50    0.20    --   60.00  76.00 -15.27   68
 45  \w     74.00 125.00   0.50    0.20    --   60.00  77.00 171.94  102
 46  \w     88.00 125.00   0.50    0.20    --   60.00  73.00  70.21   74
 47  \w     90.00 117.00   0.50    0.20    --   60.00  75.00-139.32   54
 48  \w     35.00  68.00   0.50    0.20    --   60.00  75.00-139.32   66
 49  \w     35.00  61.00   0.50    0.20    --   60.00  73.00  70.21   52
 50  \w     34.00  66.00   0.50    0.20    --   60.00  76.00 -15.27   64
 51  \w     33.00  64.00   0.50    0.20    --   60.00  77.00 171.94   62
 52  \w     38.00 119.00   0.50    0.20    --   64.00  76.00  24.46  162
 53  \w     37.00  73.00   0.50    0.20    --   64.00  77.00  88.74   72
 54  \w     98.00 124.00   0.50    0.20    --   64.00  77.00  88.74   52
 55  \w     91.00 119.00   0.50    0.20    --   64.00  70.00 130.22   56
 56  \w     39.00  76.00   0.50    0.20    --   64.00  70.00 130.22   74
 57  \w     40.00  76.00   0.50    0.20    --   64.00  73.00 -98.51   72
 58  \w     86.00 124.00   0.50    0.20    --   64.00  73.00 -98.51   76
 59  \w     42.00  70.00   0.50    0.20    --   68.00  77.00-129.57   56
 60  \w     98.00 124.00   0.50    0.20    --   68.00  77.00-129.57   52
 61  \w     47.00  97.00   0.50    0.20    --   68.00  66.00-140.03  100
 62  \w     46.00 113.00   0.50    0.20    --   68.00  63.00 -61.78  134
 63  \w     45.00 132.00   0.50    0.20    --   68.00  65.00 -24.06  174
 64  \w     45.00  78.00   0.50    0.20    --   68.00  64.00  67.33   66
 65  \w     47.00  77.00   0.50    0.20    --   72.00  75.00  90.39   60
 66  \w     55.00  81.00   0.50    0.20    --   72.00  56.00  27.39   52
 67  \w    111.00 138.00   0.50    0.20    --   72.00  75.00  90.39   54
 68  \w     51.00 141.00   0.50    0.20    --   76.00  72.00 -59.18  180
 69  \w     52.00  98.00   0.50    0.20    --   76.00  73.00-131.45   92
 70  \w     56.00 112.00   0.50    0.20    --   76.00  55.00-166.71  112
 71  \w    104.00 130.00   0.50    0.20    --   76.00  66.00 -82.83   52
 72  \w     59.00 100.00   0.50    0.20    --   76.00  66.00 -82.83   82
 73  \w     59.00  85.00   0.50    0.20    --   80.00  62.00 106.37   52
 74  \w     58.00  92.00   0.50    0.20    --   80.00  59.00   0.68   68
 75  \w     60.00  98.00   0.50    0.20    --   84.00  68.00-104.24   76
 76  \w     59.00  97.00   0.50    0.20    --   84.00  70.00 115.43   76
 77  \w    103.00 150.00   0.50    0.20    --   84.00  70.00 115.43   94
 78  \w     67.00  92.00   0.50    0.20    --   88.00  62.00 157.14   50
 79  \w    132.00 157.00   0.50    0.20    --   96.00  74.00 -62.97   50
 80  \w     70.00 100.00   0.50    0.20    --   96.00  74.00 -62.97   60
 81  \w     73.00 112.00   0.50    0.20    --  100.00  77.00 120.00   78
 82  \w     65.00 112.00   0.50    0.20    --  100.00 -53.00 -60.00   94
 83  \w     36.00 109.00   0.50    0.20    --  100.00-133.00   0.00  146
 84  \w    121.00 150.00   0.50    0.20    --  100.00  77.00 -41.69   58
 85  \w     73.00 113.00   0.50    0.20    --  100.00  77.00 -41.69   80
 86  \w     78.00 151.00   0.50    0.20    --  100.00  61.00-120.00  146
 87  \w     73.00 152.00   0.50    0.20    --  100.00  77.00  30.00  158
 88  \w     93.00 118.00   0.50    0.20    --  100.00 -45.00 -90.00   50
 89  \w     76.00 102.00   0.50    0.20    --  100.00  69.00  60.00   52
 90  \w     76.00 102.00   0.50    0.20    --  100.00  69.00-120.00   52
 91  \w    111.00 157.00   0.50    0.20    --  100.00  77.00-180.00   92
 92  \w     73.00 106.00   0.50    0.20    --  100.00  77.00-180.00   66
 93  \w     36.00  85.00   0.50    0.20    --  100.00 -45.00 -90.00   98
 94  \w     73.00 114.00   0.50    0.20    --  100.00  77.00 150.00   82
 95  \w     82.00 108.00   0.50    0.20    --  100.00 -93.00 150.00   52
 96  \w     27.00  52.00   0.50    0.20    --  100.00 -93.00 150.00   50
 97  \w     89.00 145.00   0.50    0.20    --  100.00  37.00 -30.00  112
 98  \w     68.00 114.00   0.50    0.20    --  100.00 -30.00 -90.00   92
 99  \w     69.00 123.00   0.50    0.20    --  100.00-133.00 -60.00  108
100  \w     73.00 117.00   0.50    0.20    --  100.00  77.00   0.00   88
101  \w     53.00 108.00   0.50    0.20    --  100.00 -93.00 -30.00  110
102  \w     32.00 108.00   0.50    0.20    --  100.00-111.00  90.00  152
103  \w     73.00 157.00   0.50    0.20    --  100.00  77.00  60.00  168
104  \w     76.00 131.00   0.50    0.20    --  100.00  69.00-180.00  110
105  \w     87.00 126.00   0.50    0.20    --  100.00 -86.00-150.00   78
106  \w     81.00 106.00   0.50    0.20    --  100.00 -45.00  60.00   50
107  \w     38.00 101.00   0.50    0.20    --  100.00 -61.00  90.00  126
108  \w     50.00  79.00   0.50    0.20    --  100.00 -86.00-150.00   58
109  \w     62.00 130.00   0.50    0.20    --  100.00 -15.00   0.00  136
110  \w     79.00 125.00   0.50    0.20    --  100.00  61.00  30.00   92
111  \w     88.00 155.00   0.50    0.20    --  100.00  37.00 -60.00  134
112  \w     76.00 101.00   0.50    0.20    --  100.00  69.00 -90.00   50
113  \w    124.00 150.00   0.50    0.20    --  100.00  77.00-120.00   52
114  \w     78.00 104.00   0.50    0.20    --  100.00  77.00-120.00   52
115  \w     36.00  62.00   0.50    0.20    --  100.00 -45.00  60.00   52
116  \w    113.00 150.00   0.50    0.20    --  100.00  45.00-180.00   74
117  \w    132.00 157.00   0.50    0.20    --  100.00  77.00 -90.00   50
118  \w     78.00 121.00   0.50    0.20    --  100.00  61.00  60.00   86
119  \w     73.00 106.00   0.50    0.20    --  100.00  77.00 -90.00   66
120  \w     78.00 152.00   0.50    0.20    --  100.00  61.00   0.00  148
121  \w     44.00  70.00   0.50    0.20    --  100.00-133.00-150.00   52
122  \w     98.00 123.00   0.50    0.20    --  100.00-133.00-150.00   50
123  \w    100.00 157.00   0.50    0.20    --  100.00  53.00 120.00  114
124  \w    123.00 156.00   0.50    0.20    --  100.00  77.00-150.00   66
125  \w     75.00 101.00   0.50    0.20    --  100.00  77.00-150.00   52
126  \w    106.00 156.00   0.50    0.20    --  100.00  77.00 -30.00  100
127  \w     43.00 114.00   0.50    0.20    --  100.00 -30.00 120.00  142
128  \w     74.00 134.00   0.50    0.20    --  100.00  76.00-158.92  120
129  \w     74.00 109.00   0.50    0.20    --  100.00  77.00  90.00   70
130  \w     77.00 123.00   0.50    0.20    --  100.00 178.00   0.00   92
131  \w     64.00 112.00   0.50    0.20    --  100.00 -37.00 150.00   96
132  \w     74.00 100.00   0.50    0.20    --  100.00  77.00 -60.00   52
133  \w     73.00  99.00   0.50    0.20    --  100.00  77.00 -30.00   52
134  \w     86.00 111.00   0.50    0.20    --  100.00-111.00   0.00   50
135  \w     34.00  60.00   0.50    0.20    --  100.00-111.00   0.00   52
136  \w     79.00 140.00   0.50    0.20    --  100.00  61.00 150.00  122
137  \w    115.00 149.00   0.50    0.20    --  100.00  61.00  90.00   68
138  \w     36.00 114.00   0.50    0.20    --  100.00 -53.00 120.00  156
139  \w     80.00 107.00   0.50    0.20    --  100.00  61.00  90.00   54
140  \w     91.00 143.00   0.50    0.20    --  100.00  93.00   0.00  104
141  \w    119.00 155.00   0.50    0.20    --  100.00  30.00 150.00   72
142  \w     25.00  82.00   0.50    0.20    --  100.00 -15.00 -60.00  114
143  \w    129.00 154.00   0.50    0.20    --  100.00  77.00 120.00   50
144  \w     38.00  64.00   0.50    0.20    --  100.00 -69.00 -90.00   52
145  \w     84.00 115.00   0.50    0.20    --  100.00 -69.00 -90.00   62
146  \w    108.00 154.00   0.50    0.20    --  100.00  93.00  60.00   92
147  \w     31.00 126.00   0.50    0.20    --  100.00 -86.00  90.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0710210000
_diffrn_orient_matrix_UB_12      -0.0527190000
_diffrn_orient_matrix_UB_13      0.0633638000
_diffrn_orient_matrix_UB_21      -0.0471987000
_diffrn_orient_matrix_UB_22      -0.1376130000
_diffrn_orient_matrix_UB_23      -0.0202495000
_diffrn_orient_matrix_UB_31      0.1643344000
_diffrn_orient_matrix_UB_32      -0.0166801000
_diffrn_orient_matrix_UB_33      -0.0332376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.406
_diffrn_reflns_theta_min         4.762
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.2958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3366
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01584b2.cif
_cod_data_source_block           13129-maa-2
_cod_depositor_comments
'Adding full bibliography for 7158355--7158358.cif.'
_cod_database_code               7158357
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C16H12O5N1
_reflns_odcompleteness_completeness 96.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6(2)
 0.4(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C4(H4A,H4B), C9(H9A,H9B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C6(H6), C16(H16), C10(H10), C17(H17), C18(H18), C7(H7)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              97576
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 203.197
_oxdiff_exptl_absorpt_empirical_full_min 0.413