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_7158356
_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         'C22 H25 Cl2 N O6'
_chemical_formula_sum            'C22 H25 Cl2 N O6'
_chemical_formula_weight         470.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 92.532(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0854(3)
_cell_length_b                   7.50448(14)
_cell_length_c                   22.3639(5)
_cell_measurement_reflns_used    11447
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.4200
_cell_measurement_theta_min      3.9490
_cell_volume                     2193.97(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -22.00  10.00   0.50    0.63    --  -47.20  22.00 -81.00   64
  2  \w    -67.00 -41.00   0.50    2.53    -- -106.00  61.00   0.00   52
  3  \w    -98.00 -43.00   0.50    2.53    -- -106.00  77.00  30.00  110
  4  \w    -71.00 -40.00   0.50    2.53    -- -106.00  61.00  90.00   62
  5  \w    -71.00 -40.00   0.50    2.53    -- -106.00  61.00 120.00   62
  6  \w    -94.00 -60.00   0.50    2.53    -- -106.00  77.00  60.00   68
  7  \w    -99.00 -61.00   0.50    2.53    -- -106.00  77.00  90.00   76
  8  \w    -79.00 -54.00   0.50    0.63    --  -47.20 -22.00 113.00   50
  9  \w    -25.00  19.00   0.50    0.63    --   47.20 -22.00 113.00   88
 10  \w     -7.00  62.00   0.50    0.63    --   47.20 -57.00  90.00  138
 11  \w     36.00  69.00   0.50    2.53    --  107.75 -61.00   0.00   66
 12  \w     65.00  93.00   0.50    2.53    --  107.75 -94.00   0.00   56
 13  \w     83.00 112.00   0.50    2.53    --  107.75-125.00   0.00   58
 14  \w     44.00  70.00   0.50    2.53    --  107.75-125.00 -90.00   52
 15  \w     38.00  85.00   0.50    2.53    --  107.75 -77.00 -90.00   94
 16  \w     37.00  71.00   0.50    2.53    --  107.75 -61.00-150.00   68
 17  \w     37.00  69.00   0.50    2.53    --  107.75 -61.00 -90.00   64
 18  \w     39.00  78.00   0.50    2.53    --  107.75-125.00   0.00   78
 19  \w     38.00 118.00   0.50    0.63    --   47.20  22.00 -81.00  160
 20  \w     96.00 135.00   0.50    2.53    --  107.75  22.00 -81.00   78
 21  \w    124.00 175.00   0.50    2.53    --  107.75  45.00   0.00  102
 22  \w    147.00 178.00   0.50    2.53    --  107.75  77.00 -30.00   62
 23  \w    103.00 172.00   0.50    2.53    --  107.75  45.00 -30.00  138
 24  \w     86.00 135.00   0.50    2.53    --  107.75  77.00 -30.00   98
 25  \w    -26.00  25.00   0.50    0.63    --   47.20 -19.00 -30.00  102
 26  \w    -64.00 -34.00   0.50    2.53    -- -106.00  61.00 -90.00   60
 27  \w    -63.00 -37.00   0.50    2.53    -- -106.00  61.00-120.00   52
 28  \w    -71.00 -36.00   0.50    2.53    -- -106.00  61.00-180.00   70
 29  \w   -171.00 -95.00   0.50    2.53    -- -106.00 -22.00 113.00  152
 30  \w   -176.00 -99.00   0.50    2.53    -- -106.00 -45.00  30.00  154
 31  \w    -24.00   1.00   0.50    0.63    --   47.20 -22.00 113.00   50
 32  \w     26.00  53.00   0.50    0.63    --   47.20  77.00 -30.00   54
 33  \w     73.00 108.00   0.50    0.63    --   47.20  37.00 -30.00   70
 34  \w     74.00  99.00   0.50    0.63    --   47.20 125.00-180.00   50
 35  \w     29.00  57.00   0.50    0.63    --   47.20  77.00  90.00   56
 36  \w     40.00  67.00   0.50    0.63    --   47.20  77.00   0.00   54
 37  \w     38.00  65.00   0.50    0.63    --   47.20  37.00 -30.00   54
 38  \w     25.00  69.00   0.50    0.63    --   47.20  77.00  30.00   88
 39  \w     52.00  93.00   0.50    0.63    --   47.20  37.00  30.00   82
 40  \w   -123.00 -88.00   0.50    2.53    -- -106.00 -66.00 -26.42   70
 41  \w   -115.00-107.50   0.50    2.53    -- -106.00 -63.00 -13.18   15
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319314000
_diffrn_orient_matrix_UB_12      -0.0567065000
_diffrn_orient_matrix_UB_13      0.0643404000
_diffrn_orient_matrix_UB_21      -0.1134349000
_diffrn_orient_matrix_UB_22      -0.0166777000
_diffrn_orient_matrix_UB_23      0.0149239000
_diffrn_orient_matrix_UB_31      0.0003743000
_diffrn_orient_matrix_UB_32      -0.1965924000
_diffrn_orient_matrix_UB_33      -0.0198010000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21013
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         3.841
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0439P)^2^+0.7992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3811
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01584b2.cif
_cod_data_source_block           17723_mme-6
_cod_depositor_comments
'Adding full bibliography for 7158355--7158358.cif.'
_cod_database_code               7158356
_shelx_shelxl_version_number     2014/7
_diffrn_oxdiff_digest_frames
;
0127f9cfa3ba027cbfd235253afde23dce000284cef
;
_diffrn_oxdiff_digest_hkl
;
0191ba616bd7e0766f4a7f92dcff203710f93e
;
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C8(H8), C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C3(H3), C20(H20), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              87542
_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 2.239
_oxdiff_exptl_absorpt_empirical_full_min 0.659