Enantiospecific Aluminum-Catalyzed (3+2) Cycloaddition of Unactivated Aziridines with Isothiocyanates.
Sengoden, Mani; Irie, Ryo; Punniyamurthy, Tharmalingam; The Journal of organic chemistry 81 (2016) 11508–11513; doi:10.1021/acs.joc.6b02190

data_4037399
_publ_section_title
;
 Enantiospecific Aluminum-Catalyzed (3+2) Cycloaddition of Unactivated
 Aziridines with Isothiocyanates.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11508
_journal_page_last               11513
_journal_paper_doi               10.1021/acs.joc.6b02190
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C18 H20 N2 S'
_chemical_formula_sum            'C18 H20 N2 S'
_chemical_formula_weight         296.42
_chemical_name_systematic
(R,Z)-N-(3-Isopropyl-5-phenylthiazolidin-2-ylidene)aniline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0184(6)
_cell_length_b                   11.6977(8)
_cell_length_c                   15.8224(10)
_cell_measurement_reflns_used    1782
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.99
_cell_measurement_theta_min      2.57
_cell_volume                     1669.18(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Wingx
_computing_publication_material  Wingx
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12947
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.411
_diffrn_reflns_theta_min         2.165
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.956
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.881
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0817
_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^)+(0.1240P)^2^+0.6648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2266
_refine_ls_wR_factor_ref         0.2662
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2012
_reflns_number_total             3804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02190_si_002.cif
_cod_data_source_block           3a
_cod_database_code               4037399
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              81907
_shelx_hkl_checksum              55129