Cycloaddition of <i>N</i>-arylnitrones with donor-acceptor oxiranes <i>via</i> C-C bond cleavage to construct 1,5,2-dioxazinanes.
Li, Wenhui; Lin, Jianying; Huang, Shuangping; Liu, Qiang; Wei, Wenlong; Li, Xing; Organic & biomolecular chemistry 21 (2023) 6778–6782; doi:10.1039/d3ob00375b

data_7159528
_publ_section_title
;
 Cycloaddition of <i>N</i>-arylnitrones with donor-acceptor oxiranes
 <i>via</i> C-C bond cleavage to construct 1,5,2-dioxazinanes.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6778
_journal_page_last               6782
_journal_paper_doi               10.1039/d3ob00375b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C28 H29 N O6'
_chemical_formula_sum            'C28 H29 N O6'
_chemical_formula_weight         475.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-08-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-23 deposited with the CCDC.	2023-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.66800(10)
_cell_length_b                   16.9490(2)
_cell_length_c                   30.1249(4)
_cell_measurement_reflns_used    16075
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1010
_cell_measurement_theta_min      3.9350
_cell_volume                     4936.35(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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      1.00  75.00   1.00    1.00    --   35.62 -99.00 -30.00   74
  2  \w      1.00  75.00   1.00    1.00    --   35.62 -99.00 120.00   74
  3  \w     55.00 108.00   1.00    1.00    --   35.62-178.00 120.00   53
  4  \w     19.00 103.00   1.00    1.00    --   35.62  57.00   0.00   84
  5  \w     17.00 105.00   1.00    1.00    --   35.62  38.00-180.00   88
  6  \w      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
  7  \w     17.00 105.00   1.00    1.00    --   35.62  38.00  90.00   88
  8  \w     19.00 103.00   1.00    1.00    --   35.62  57.00 -60.00   84
  9  \w     19.00 103.00   1.00    1.00    --   35.62  57.00-150.00   84
 10  \w     38.00 110.00   1.00    3.49    --  107.12 -95.00 -30.00   72
 11  \w     38.00 110.00   1.00    3.49    --  107.12 -95.00-180.00   72
 12  \w     86.00 177.00   1.00    3.49    --  107.12  30.00-150.00   91
 13  \w     38.00 128.00   1.00    3.49    --  107.12 -30.00 -60.00   90
 14  \w     68.00 107.00   1.00    3.49    --  107.12-111.00  90.00   39
 15  \w     68.00  99.00   1.00    3.49    --  107.12 178.00   0.00   31
 16  \w     53.00 120.00   1.00    3.49    --  107.12 -61.00 -30.00   67
 17  \w     39.00 110.00   1.00    3.49    --  107.12 -45.00  60.00   71
 18  \w     41.00 120.00   1.00    3.49    --  107.12 -61.00-120.00   79
 19  \w    140.00 166.00   1.00    3.49    --  107.12  45.00 -60.00   26
 20  \w     94.00 174.00   1.00    3.49    --  107.12  45.00 -30.00   80
 21  \w     91.00 118.00   1.00    3.49    --  107.12  45.00 -90.00   27
 22  \w     91.00 124.00   1.00    3.49    --  107.12  45.00 -60.00   33
 23  \w     57.00 113.00   1.00    3.49    --  107.12-111.00 -90.00   56
 24  \w     57.00 108.00   1.00    3.49    --  107.12 -95.00 120.00   51
 25  \w     44.00 124.00   1.00    3.49    --  107.12 -45.00 120.00   80
 26  \w     88.00 169.00   1.00    3.49    --  107.12  30.00 120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0505808000
_diffrn_orient_matrix_UB_12      0.0182188000
_diffrn_orient_matrix_UB_13      0.0474094000
_diffrn_orient_matrix_UB_21      -0.0805360000
_diffrn_orient_matrix_UB_22      -0.0784186000
_diffrn_orient_matrix_UB_23      0.0006720000
_diffrn_orient_matrix_UB_31      0.1278107000
_diffrn_orient_matrix_UB_32      -0.0421988000
_diffrn_orient_matrix_UB_33      0.0191863000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            37505
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.525
_diffrn_reflns_theta_min         5.219
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0697P)^2^+1.1905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4216
_reflns_number_total             4780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00375b2.cif
_cod_data_source_block           zjh-1-20220729
_cod_depositor_comments          'Adding full bibliography for 7159528.cif.'
_cod_original_cell_volume        4936.36(10)
_cod_database_code               7159528
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.911
_diffrn_oxdiff_digest_frames
;
01ed4955694b06ceb228968870fc981adb00029c502
;
_diffrn_oxdiff_digest_hkl
;
011c4ee69d148952058319472ace2ff4625864
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C12(H12), C8(H8), C17(H17), C15(H15), C16(H16), C20(H20),
 C11(H11), C10(H10), C23(H23), C9(H9), C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C34(H34A,H34B,H34C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              73828
_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 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.634