Catalytic Regioselectivity Control in Ring-Opening Cycloisomerization of Methylene- or Alkylidenecyclopropyl Ketones
Shengming Ma; Lianghua Lu; Junliang Zhang; Journal of the American Chemical Society 126 (2004) 9645–9660; doi:10.1021/ja0494860

data_4112838
_publ_section_title
;
 Catalytic Regioselectivity Control in Ring-Opening Cycloisomerization of
 Methylene- or Alkylidenecyclopropyl Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9645
_journal_page_last               9660
_journal_paper_doi               10.1021/ja0494860
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C16 H20 O3 S'
_chemical_formula_weight         292.38
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_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                109.621(2)
_cell_angle_beta                 94.117(2)
_cell_angle_gamma                101.647(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9721(9)
_cell_length_b                   9.2400(11)
_cell_length_c                   11.3859(13)
_cell_measurement_reflns_used    1089
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.283
_cell_measurement_theta_min      4.822
_cell_volume                     764.84(15)
_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 0.910
_diffrn_measured_fraction_theta_max 0.910
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4763
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53020
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                1884
_reflns_number_total             3441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0494860si20040203_124638.cif
_cod_data_source_block           3g
_cod_database_code               4112838