Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines by regioselective [3 + 2] annulations of ketenimines with donor–acceptor oxiranes and aziridines
Alajarin, Mateo; Bañon, Daniel; Egea, Adrian; Marín-Luna, Marta; Orenes, Raul-Angel; Vidal, Angel; Organic Chemistry Frontiers 5 (2018) 2020–; doi:10.1039/C8QO00255J

data_1554295
_publ_section_title
;
 Accessing polysubstituted oxazolidines, pyrrolidines and imidazolidines
 by regioselective [3 + 2] annulations of ketenimines with donor--acceptor
 oxiranes and aziridines
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2020
_journal_paper_doi               10.1039/C8QO00255J
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C44 H44 Cl2 N2 O6 S'
_chemical_formula_weight         799.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-02-09 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1688(9)
_cell_length_b                   18.3501(10)
_cell_length_c                   11.8464(7)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.22
_cell_volume                     3949.6(4)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2011)'
_computing_data_collection       'APEX 2013.2 (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            210453
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_min         2.220
_diffrn_source                   'high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7406
_exptl_absorpt_correction_T_min  0.7164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 4219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         12107
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0612P)^2^+3.2446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                10316
_reflns_number_total             12107
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00255j2.cif
_cod_data_source_block           DBG_dicloro2
_cod_database_code               1554295
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.914
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              12969
_shelx_hkl_checksum              58716