Formal Homoiodo Allylsilane Annulations: Dual Total Syntheses of (\±)-Hirsutene and (\±)-Capnellene
Shou-Jie Shen; Wei-Dong Z. Li; Journal of Organic Chemistry 78 (2013) 7112–7120; doi:10.1021/jo4009854

data_4028438
_publ_section_title
;
 Formal Homoiodo Allylsilane Annulations: Dual Total Syntheses of
 (\+-)-Hirsutene and (\+-)-Capnellene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7112
_journal_page_last               7120
_journal_paper_doi               10.1021/jo4009854
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C22 H28 Br N O2'
_chemical_formula_weight         418.36
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 123.324(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.002(4)
_cell_length_b                   24.264(8)
_cell_length_c                   9.485(3)
_cell_measurement_reflns_used    1545
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.83
_cell_measurement_theta_min      2.37
_cell_volume                     2115.7(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5419
_diffrn_reflns_theta_full        24.83
_diffrn_reflns_theta_max         24.83
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    1.958
_exptl_absorpt_correction_T_max  0.7578
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0205P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                2235
_reflns_number_total             3124
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4009854_si_002.cif
_cod_data_source_block           cc
_cod_original_cell_volume        2115.7(12)
_cod_database_code               4028438