[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_4032898
_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         'C19 H19 N O4'
_chemical_formula_sum            'C19 H19 N O4'
_chemical_formula_weight         325.35
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   35.153(2)
_cell_length_b                   35.153(2)
_cell_length_c                   8.9968(5)
_cell_measurement_reflns_used    2940
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.7720
_cell_measurement_theta_min      4.0310
_cell_volume                     9628.2(9)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6780
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.010
_exptl_crystal_description       Block
_exptl_crystal_F_000             3096
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_platon_squeeze_details
;
TITL 20170707-heyun-lzr-8-2_a.res in R-3
CELL   35.1530   35.1530    8.9968     90.00     90.00    120.00
SPGR R-3
C101 1.000 1.000 0.000 !       1.53 eA-3
C102 0.424 0.610 0.377 !       1.16 eA-3
C103 0.633 0.313 0.284 !       1.02 eA-3
C104 0.701 0.438 0.132 !       1.00 eA-3
C105 0.248 0.570 0.292 !       0.88 eA-3
C106 0.460 0.673 0.224 !       0.83 eA-3
C107 0.585 0.251 0.091 !       0.82 eA-3
C108 0.966 0.922 0.433 !       0.80 eA-3
C109 0.311 0.556 0.037 !       0.80 eA-3
C110 0.274 0.569 0.220 !       0.79 eA-3
C111 0.691 0.331 0.186 !       0.77 eA-3
C112 0.258 0.624 0.466 !       0.75 eA-3
C113 0.071 0.053 0.318 !       0.73 eA-3
C114 0.445 0.646 0.401 !       0.73 eA-3
C115 0.056 0.056 0.251 !       0.70 eA-3
C116 0.640 0.289 0.055 !       0.65 eA-3
C117 0.608 0.311 0.037 !       0.62 eA-3
C118 0.289 0.643 0.279 !       0.62 eA-3
C119 0.187 0.574 0.240 !       0.61 eA-3
C120 0.442 0.719 0.127 !       0.59 eA-3
C121 0.649 0.379 0.619 !       0.59 eA-3
C122 0.983 0.864 0.369 !       0.59 eA-3
C123 0.890 0.943 0.566 !       0.57 eA-3
C124 0.346 0.688 0.113 !       0.53 eA-3
;
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0648P)^2^+10.0918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3051
_reflns_number_total             4359
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01728_si_002.cif
_cod_data_source_block           lzr_sq_compound_8
_cod_depositor_comments
'Adding full bibliography for 4032895--4032898.cif.'
_cod_original_cell_volume        9628.3(12)
_cod_database_code               4032898
_shelx_shelxl_version_number     2014/7
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C9(H9), C10(H10), C19(H19), C15(H15), C18(H18), C17(H17),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_platon_squeeze_void_probe_radius 1.20
_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.821