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_4022743
_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            'C11 H20 O'
_chemical_formula_weight         168.27
_space_group_IT_number           82
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      82
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.694(2)
_cell_length_b                   15.694(2)
_cell_length_c                   8.2592(12)
_cell_measurement_temperature    143(1)
_cell_volume                     2034.2(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8331
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4739
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(4)
_refine_ls_extinction_coef       0.000(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   1.401
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.401
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.1060
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3133
_refine_ls_wR_factor_ref         0.3359
_reflns_number_gt                1472
_reflns_number_total             1785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062292dsi20061107_122938.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'I -4 '
_cod_database_code               4022743