AlCl3-promoted [3 + 2] annulation of cis-2,3-disubstituted cyclopropane 1,1-diesters with isothiocyanates: stereoselective synthesis of densely substituted 2-iminodihydrothiophenes.
Sun, Yongxian; Yang, Gaosheng; Chai, Zhuo; Mu, Xiaolong; Chai, Jun; Organic & biomolecular chemistry 11 (2013) 7859–7868; doi:10.1039/c3ob41678j

data_7153171
_publ_section_title
;
 AlCl3-promoted [3 + 2] annulation of cis-2,3-disubstituted cyclopropane
 1,1-diesters with isothiocyanates: stereoselective synthesis of densely
 substituted 2-iminodihydrothiophenes.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7859
_journal_page_last               7868
_journal_paper_doi               10.1039/c3ob41678j
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C29 H25 Br Cl N O5 S'
_chemical_formula_weight         614.92
_chemical_name_systematic
; 
 (trans, Z)-Diethyl 4-benzoyl-2-((4-bromophenyl)imino)-5-
(4-chlorophenyl)dihydrothiophene-3,3 (2H)-dicarboxylate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.1760(10)
_cell_angle_beta                 108.7200(10)
_cell_angle_gamma                109.6140(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7403(9)
_cell_length_b                   12.5649(12)
_cell_length_c                   13.0243(12)
_cell_measurement_temperature    293(2)
_cell_volume                     1411.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12325
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    1.664
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.398
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6387
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1949P)^2^+0.5637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2435
_refine_ls_wR_factor_ref         0.2769
_reflns_number_gt                4235
_reflns_number_total             6387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41678j.txt
_cod_data_source_block           121101b_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153171