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_4112841
_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            'C12 H11 Cl O3 S'
_chemical_formula_weight         270.72
_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                82.377(2)
_cell_angle_beta                 68.451(2)
_cell_angle_gamma                75.268(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6277(7)
_cell_length_b                   9.1238(9)
_cell_length_c                   9.5937(9)
_cell_measurement_reflns_used    2269
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.420
_cell_measurement_theta_min      4.569
_cell_volume                     600.01(10)
_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 0.885
_diffrn_measured_fraction_theta_max 0.885
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3607
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69496
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.405
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0603P)^2^+0.1335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                2404
_reflns_number_total             2625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0494860si20040203_125126.cif
_cod_data_source_block           20l
_cod_database_code               4112841