Studies on the formal [3 + 2] cycloaddition of aziridines with alkenes for the synthesis of 1-azaspiroalkanes.
Martinand-Lurin, Elodie; Gruber, Raymond; Retailleau, Pascal; Fleurat-Lessard, Paul; Dauban, Philippe; The Journal of organic chemistry 80 (2015) 1414–1426; doi:10.1021/jo502333j

data_4030464
_publ_section_title
;
 Studies on the formal [3 + 2] cycloaddition of aziridines with alkenes
 for the synthesis of 1-azaspiroalkanes.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1414
_journal_page_last               1426
_journal_paper_doi               10.1021/jo502333j
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C17 H22 Cl3 N O3 S'
_chemical_formula_sum            'C17 H22 Cl3 N O3 S'
_chemical_formula_weight         426.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.345(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.259(3)
_cell_length_b                   5.923(1)
_cell_length_c                   17.597(3)
_cell_measurement_reflns_used    1357
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      4.8
_cell_volume                     1908.3(6)
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_sigmaI/netI    0.1217
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5106
_diffrn_reflns_point_group_measured_fraction_max 0.739
_diffrn_reflns_theta_max         62.956
_diffrn_reflns_theta_min         6.531
_exptl_absorpt_coefficient_mu    5.516
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin elongated stick'
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.536
_refine_diff_density_min         -1.042
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.55(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     268
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0884
_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^)+(0.0914P)^2^+6.4717P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2071
_refine_ls_wR_factor_ref         0.2476
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_full    0.434
_reflns_Friedel_fraction_max     0.487
_reflns_number_gt                1619
_reflns_number_total             2287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502333j_si_006.cif
_cod_data_source_block           compound_2ec
_cod_depositor_comments
'Adding full bibliography for 4030461--4030470.cif.'
_cod_original_cell_volume        1908.3(7)
_cod_database_code               4030464
_shelxl_version_number           2012-9
_shelx_res_checksum              90616
_shelx_hkl_checksum              65626