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_7158358
_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   mixed
_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                 109.369(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9201(3)
_cell_length_b                   27.3837(9)
_cell_length_c                   9.5899(3)
_cell_measurement_reflns_used    11999
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      76.9400
_cell_measurement_theta_min      5.1350
_cell_volume                     2209.90(14)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.965
_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    -26.00  27.00   0.50    0.66    --  -47.20  19.00-120.00  106
  2  \w     67.00  92.00   0.50    0.66    --   47.20 142.00 -87.00   50
  3  \w     74.00 120.00   0.50    0.66    --   47.20 125.00 -90.00   92
  4  \w     93.00 118.00   0.50    2.63    --  107.75 142.00 -87.00   50
  5  \w    141.00 174.00   0.50    2.63    --  107.75  45.00-150.00   66
  6  \w    108.00 141.00   0.50    2.63    --  107.75  30.00 -90.00   66
  7  \w     99.00 143.00   0.50    2.63    --  107.75  30.00-150.00   88
  8  \w     53.00  98.00   0.50    2.63    --  107.75 -94.00  30.00   90
  9  \w     76.00 103.00   0.50    2.63    --  107.75 -94.00  60.00   54
 10  \w     87.00 112.00   0.50    2.63    --  107.75-125.00  90.00   50
 11  \w     50.00  75.00   0.50    2.63    --  107.75-128.00  26.00   50
 12  \w     35.00  61.00   0.50    2.63    --  107.75 -94.00  60.00   52
 13  \w     49.00  75.00   0.50    2.63    --  107.75 -77.00  90.00   52
 14  \w     35.00  71.00   0.50    2.63    --  107.75 -61.00 150.00   72
 15  \w     43.00  69.00   0.50    2.63    --  107.75-125.00  90.00   52
 16  \w     38.00  71.00   0.50    2.63    --  107.75 -61.00 -90.00   66
 17  \w     70.00 105.00   0.50    2.63    --  107.75 -94.00 -90.00   70
 18  \w     67.00 121.00   0.50    2.63    --  107.75-142.00-144.00  108
 19  \w     39.00  64.00   0.50    2.63    --  107.75-142.00-144.00   50
 20  \w     32.00 111.00   0.50    0.66    --   47.20  57.00-150.00  158
 21  \w    129.00 178.00   0.50    2.63    --  107.75  61.00  90.00   98
 22  \w    144.00 178.00   0.50    2.63    --  107.75  45.00 150.00   68
 23  \w     82.00 152.00   0.50    2.63    --  107.75 128.00 101.00  140
 24  \w    -68.00 -41.00   0.50    0.66    --  -47.20 128.00 101.00   54
 25  \w    -65.00 -40.00   0.50    2.63    -- -106.00  61.00  60.00   50
 26  \w    -70.00 -35.00   0.50    2.63    -- -106.00  61.00  90.00   70
 27  \w    -66.00 -41.00   0.50    2.63    -- -106.00 128.00  39.43   50
 28  \w    -97.00 -72.00   0.50    2.63    -- -106.00 128.00 101.00   50
 29  \w   -113.00 -72.00   0.50    2.63    -- -106.00 128.00  39.43   82
 30  \w   -107.00 -44.00   0.50    2.63    -- -106.00 108.00  74.45  126
 31  \w    -95.00 -62.00   0.50    0.66    --  -47.20 142.00 -87.00   66
 32  \w   -124.00 -89.00   0.50    2.63    -- -106.00 142.00 -87.00   70
 33  \w   -176.00 -89.00   0.50    2.63    -- -106.00 -61.00 -60.00  174
 34  \w   -120.00 -64.00   0.50    0.66    --  -47.20-142.00-144.00  112
 35  \w   -109.00 -84.00   0.50    0.66    --  -47.20-128.00  26.00   50
 36  \w   -112.00 -86.00   0.50    0.66    --  -47.20-125.00  90.00   52
 37  \w     78.00  91.50   0.50    2.63    --  107.75 142.00 -87.00   27
;
_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      -0.1165386000
_diffrn_orient_matrix_UB_12      0.0245895000
_diffrn_orient_matrix_UB_13      -0.1380428000
_diffrn_orient_matrix_UB_21      0.0637612000
_diffrn_orient_matrix_UB_22      0.0505177000
_diffrn_orient_matrix_UB_23      0.0628566000
_diffrn_orient_matrix_UB_31      0.1259790000
_diffrn_orient_matrix_UB_32      -0.0027954000
_diffrn_orient_matrix_UB_33      -0.0774090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18890
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.385
_diffrn_reflns_theta_min         3.228
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57707
_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_density_diffrn    1.414
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0479P)^2^+0.5778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4131
_reflns_number_total             4524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01584b2.cif
_cod_data_source_block           16022_apm-502
_cod_depositor_comments
'Adding full bibliography for 7158355--7158358.cif.'
_cod_database_code               7158358
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 H25 Cl2 N O6 '
_diffrn_oxdiff_digest_frames
;
01c30885d407c795486d59e9060a2bc80a000301baf
;
_diffrn_oxdiff_digest_hkl
;
01774a2b7b5419d7f27d00fb9b6948f3ff815d
;
_reflns_odcompleteness_completeness 98.29
_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, 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:
 C20(H20), C10(H10), C18(H18), C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C17(H17A,H17B), C16(H16A,H16B), C21(H21A,H21B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C5(H5A,H5B,H5C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              91998
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.631