2,3,4- or 2,3,5-Trisubstituted Furans: Catalyst-Controlled Highly Regioselective Ring-Opening Cycloisomerization Reaction of Cyclopropenyl Ketones
Shengming Ma; Junliang Zhang; Journal of the American Chemical Society 125 (2003) 12386–12387; doi:10.1021/ja036616g

data_4114251
_publ_section_title
;
 2,3,4- or 2,3,5-Trisubstituted Furans: Catalyst-Controlled Highly
 Regioselective Ring-Opening Cycloisomerization Reaction of Cyclopropenyl
 Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12386
_journal_page_last               12387
_journal_paper_doi               10.1021/ja036616g
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C15 H18 O3 S'
_chemical_formula_weight         278.35
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0416(9)
_cell_length_b                   15.7116(11)
_cell_length_c                   15.1600(11)
_cell_measurement_reflns_used    2313
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.388
_cell_measurement_theta_min      5.038
_cell_volume                     2868.2(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16943
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76338
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6452
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.792
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0136P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                3776
_reflns_number_total             6452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036616gsi20030611_083444.cif
_cod_data_source_block           cd2370
_cod_database_code               4114251