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_7158355
_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_formula_moiety         'C20 H25 N O5'
_chemical_formula_sum            'C20 H25 N O5'
_chemical_formula_weight         359.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_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                 106.000(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5595(2)
_cell_length_b                   7.54710(10)
_cell_length_c                   18.0224(3)
_cell_measurement_reflns_used    5210
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.0770
_cell_measurement_theta_min      3.3900
_cell_volume                     1772.87(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_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    -50.00 -18.00   0.50    0.21    --  -38.82 137.00 166.00   64
  2  \w    -88.00 -62.00   0.50    0.21    --  -38.82 137.00 166.00   52
  3  \w     25.00  63.00   0.50    0.21    --   38.82-137.00 102.00   76
  4  \w     72.00 119.00   0.50    0.83    --  100.00-137.00 102.00   94
  5  \w     93.00 119.00   0.50    0.83    --  100.00 137.00 166.00   52
  6  \w     83.00 109.00   0.50    0.83    --  100.00-132.00 -79.00   52
  7  \w     36.00  62.00   0.50    0.83    --  100.00-137.00 102.00   52
  8  \w     90.00 140.00   0.50    0.83    --  100.00 132.00 -10.00  100
  9  \w    -71.00 -45.00   0.50    0.21    --  -38.82 132.00 -10.00   52
 10  \w    -42.00   6.00   0.50    0.21    --  -38.82 104.00 -30.00   96
 11  \w    -52.00  27.00   0.50    0.21    --  -38.82  43.00   0.00  158
 12  \w     27.00  75.00   0.50    0.21    --   38.82-104.00 -60.00   96
 13  \w     71.00 106.00   0.50    0.21    --   38.82  21.00 120.00   70
 14  \w     51.00 100.00   0.50    0.21    --   38.82  54.00-150.00   98
 15  \w     26.00  64.00   0.50    0.21    --   38.82  43.00  90.00   76
 16  \w     -4.00  23.00   0.50    0.21    --   38.82-104.00 -60.00   54
 17  \w     19.00 110.00   0.50    0.21    --   38.82  21.00-150.00  182
 18  \w     26.00 103.00   0.50    0.21    --   38.82  54.00  30.00  154
 19  \w     37.00  62.00   0.50    0.21    --   38.82-132.00 -79.00   50
 20  \w     51.00  88.00   0.50    0.21    --   38.82-138.00-180.00   74
 21  \w    121.00 147.00   0.50    0.83    --  100.00  77.00  30.00   52
 22  \w     55.00 105.00   0.50    0.83    --  100.00 -93.00  30.00  100
 23  \w     83.00 118.00   0.50    0.83    --  100.00  77.00  30.00   70
 24  \w    125.00 156.00   0.50    0.83    --  100.00  93.00  90.00   62
 25  \w     40.00  86.00   0.50    0.83    --  100.00-111.00  90.00   92
 26  \w     84.00 146.00   0.50    0.83    --  100.00 111.00  30.00  124
 27  \w     85.00 157.00   0.50    0.83    --  100.00 111.00  60.00  144
 28  \w    118.00 144.00   0.50    0.83    --  100.00  45.00 -60.00   52
 29  \w     84.00 110.00   0.50    0.83    --  100.00  45.00 -60.00   52
 30  \w     79.00 116.00   0.50    0.83    --  100.00-133.00  30.00   74
 31  \w     43.00  69.00   0.50    0.83    --  100.00-133.00  30.00   52
 32  \w     73.00 132.00   0.50    0.83    --  100.00 133.00  90.00  118
 33  \w     72.00 100.00   0.50    0.83    --  100.00  15.00  30.00   56
 34  \w    122.00 148.00   0.50    0.83    --  100.00  15.00  30.00   52
 35  \w     84.00 154.00   0.50    0.83    --  100.00 133.00 120.00  140
 36  \w     54.00  98.00   0.50    0.83    --  100.00 -86.00 150.00   88
 37  \w     83.00 108.00   0.50    0.83    --  100.00-111.00 -60.00   50
 38  \w     51.00  76.00   0.50    0.83    --  100.00-111.00  30.00   50
 39  \w     48.00 118.00   0.50    0.83    --  100.00-133.00 -90.00  140
 40  \w     35.00 122.00   0.50    0.83    --  100.00 -61.00-120.00  174
 41  \w     54.00  97.00   0.50    0.83    --  100.00 -93.00 -90.00   86
 42  \w     93.00 155.00   0.50    0.83    --  100.00 111.00-150.00  124
;
_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      0.0663382000
_diffrn_orient_matrix_UB_12      -0.1432669000
_diffrn_orient_matrix_UB_13      -0.0237735000
_diffrn_orient_matrix_UB_21      0.0636913000
_diffrn_orient_matrix_UB_22      0.1454288000
_diffrn_orient_matrix_UB_23      -0.0251791000
_diffrn_orient_matrix_UB_31      0.0742656000
_diffrn_orient_matrix_UB_32      0.0031192000
_diffrn_orient_matrix_UB_33      0.0818858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10486
_diffrn_reflns_theta_full        70.3352
_diffrn_reflns_theta_max         70.34
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3465
_exptl_crystal_description       needle
_exptl_crystal_F_000             770.6136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.2503
_refine_diff_density_min         -0.2486
_refine_diff_density_rms         0.0482
_refine_ls_d_res_high            0.8187
_refine_ls_d_res_low             13.0342
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0359
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.6958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2954
_reflns_number_total             3378
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ob01584b2.cif
_cod_data_source_block           16022_APM-501
_cod_depositor_comments
'Adding full bibliography for 7158355--7158358.cif.'
_cod_database_code               7158355
_chemical_oxdiff_formula         'C20 H25 N O5 '
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C4(H4a,H4b), C7(H7a,H7b), C8(H8a,H8b), C5(H5a,H5b), C6(H6a,H6b)
2.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C14(H14), C13(H13)
2.e Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C18(H18a,H18b,H18c)
;
_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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.879