Highly Enantioselective Proton-Initiated Polycyclization of Polyenes
Karavadhi Surendra; E. J. Corey; Journal of the American Chemical Society 134 (2012) 11992–11994; doi:10.1021/ja305851h

data_4118391
_publ_section_title
;
 Highly Enantioselective Proton-Initiated Polycyclization of Polyenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11992
_journal_page_last               11994
_journal_paper_doi               10.1021/ja305851h
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_sum            'C21 H26'
_chemical_formula_weight         278.42
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 103.336(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.3125(17)
_cell_length_b                   7.4191(6)
_cell_length_c                   24.023(2)
_cell_measurement_reflns_used    5475
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      14.3
_cell_measurement_theta_min      2.51
_cell_volume                     3175.8(5)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_radiation_monochromator  'Si 1 1 1'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.1222
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32027
_diffrn_reflns_theta_full        14.27
_diffrn_reflns_theta_max         14.27
_diffrn_reflns_theta_min         1.01
_exptl_absorpt_coefficient_mu    0.032
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0664P)^2^+0.7940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                3932
_reflns_number_total             5562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305851h_si_002.cif
_cod_data_source_block           KSR-7
_cod_database_code               4118391