[3 + 2] Cycloaddition of Azaoxyallyl Cations with Cyclic Ketones: Access to Spiro-4-oxazolidinones.
Shao, Pan-Lin; Li, Zi-Rui; Wang, Zhi-Peng; Zhou, Ming-Hui; Wu, Qi; Hu, Ping; He, Yun; The Journal of organic chemistry 82 (2017) 10680–10686; doi:10.1021/acs.joc.7b01728

data_4032896
_publ_section_title
;
 [3 + 2] Cycloaddition of Azaoxyallyl Cations with Cyclic Ketones: Access
 to Spiro-4-oxazolidinones.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10680
_journal_page_last               10686
_journal_paper_doi               10.1021/acs.joc.7b01728
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C26 H23 N O4'
_chemical_formula_sum            'C26 H23 N O4'
_chemical_formula_weight         413.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                115.323(7)
_cell_angle_beta                 99.995(6)
_cell_angle_gamma                110.986(7)
_cell_formula_units_Z            2
_cell_length_a                   11.0525(8)
_cell_length_b                   11.1109(8)
_cell_length_c                   11.4881(8)
_cell_measurement_reflns_used    3245
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.7770
_cell_measurement_theta_min      3.3710
_cell_volume                     1097.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.8394
_diffrn_measurement_details
;
  1 omega  -25.00   15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -60.0000 40

  2 omega  -84.00  -49.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000 -180.0000 35

  3 omega  -18.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -150.0000 26

  4 omega  -22.00   19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000   30.0000 41

  5 omega  -46.00   16.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -57.0000    0.0000 62

  6 omega   -1.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000 -150.0000 87

  7 omega  -55.00   38.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000   30.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0348255000
_diffrn_orient_matrix_UB_12      -0.0547045000
_diffrn_orient_matrix_UB_13      -0.0728203000
_diffrn_orient_matrix_UB_21      -0.0533899000
_diffrn_orient_matrix_UB_22      0.0211267000
_diffrn_orient_matrix_UB_23      -0.0022760000
_diffrn_orient_matrix_UB_31      0.0386553000
_diffrn_orient_matrix_UB_32      0.0555783000
_diffrn_orient_matrix_UB_33      -0.0134322000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9145
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.246
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.1158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3121
_reflns_number_total             4480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01728_si_002.cif
_cod_data_source_block           161213_s1_wz_compound_6a
_cod_depositor_comments
'Adding full bibliography for 4032895--4032898.cif.'
_cod_original_cell_volume        1097.77(15)
_cod_database_code               4032896
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'