[3+3] Annulation of donor-acceptor cyclopropanes with mercaptoacetaldehyde: application to the synthesis of tetrasubstituted thiophenes
Gopal Sathishkannan; Kannupal Srinivasan; Chem.Commun. 50 (2014) 4062–; doi:10.1039/C4CC00565A

data_7112210
_publ_section_title
;
 [3+3] Annulation of donor-acceptor cyclopropanes with
 mercaptoacetaldehyde: application to the synthesis of tetrasubstituted
 thiophenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              4062
_journal_paper_doi               10.1039/C4CC00565A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C21 H17 F O3 S'
_chemical_formula_weight         368.41
_chemical_name_systematic
; 
 ? 
;
_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                81.7180(10)
_cell_angle_beta                 70.6370(10)
_cell_angle_gamma                77.6340(10)
_cell_formula_units_Z            2
_cell_length_a                   9.10000(10)
_cell_length_b                   9.21500(10)
_cell_length_c                   11.4230(2)
_cell_measurement_reflns_used    8426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.799
_cell_measurement_theta_min      2.411
_cell_volume                     879.97(2)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15170
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9489
_exptl_absorpt_correction_T_min  0.9156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.2867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2735
_reflns_number_total             3092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00565a2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7112210