Construction of Bicyclic Ring Systems via a Transannular SmI~2~-Mediated Ketone-Olefin Cyclization Strategy
Gary A. Molander; Barbara Czakó; Michael Rheam; Journal of Organic Chemistry 72 (2007) 1755–1764; doi:10.1021/jo062292d

data_4022742
_publ_section_title
;
 Construction of Bicyclic Ring Systems via a Transannular
 SmI~2~-Mediated Ketone-Olefin Cyclization Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1755
_journal_page_last               1764
_journal_paper_doi               10.1021/jo062292d
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C9 H15 O'
_chemical_formula_weight         139.21
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   12.2331(7)
_cell_length_b                   12.2331(7)
_cell_length_c                   27.5112(12)
_cell_measurement_temperature    143(1)
_cell_volume                     3565.4(3)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9373
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8923
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             1386
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0529P)^2^+7.0085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                1310
_reflns_number_total             1413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062292dsi20061107_122917.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'R -3     '
_cod_database_code               4022742