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_4112840
_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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.267(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3404(19)
_cell_length_b                   10.0567(17)
_cell_length_c                   12.770(2)
_cell_measurement_reflns_used    714
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.346
_cell_measurement_theta_min      5.371
_cell_volume                     1317.0(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 0.925
_diffrn_measured_fraction_theta_max 0.925
_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  0.1005
_diffrn_reflns_av_sigmaI/netI    0.1460
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7763
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55493
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0055(6)
_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   0.722
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.723
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0067P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                1280
_reflns_number_total             3016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0494860si20040203_125100.cif
_cod_data_source_block           1l
_cod_original_formula_sum        'C12 H11  O3 S Cl'
_cod_database_code               4112840