Enantioselective Cycloisomerization of 1,6-Enynes to Bicyclo[3.1.0]hexanes Catalyzed by Rhodium and Benzoic Acid.
Masutomi, Koji; Noguchi, Keiichi; Tanaka, Ken; Journal of the American Chemical Society 136 (2014) 7627–7630; doi:10.1021/ja504048u

data_4121832
_publ_section_title
;
 Enantioselective Cycloisomerization of 1,6-Enynes to
 Bicyclo[3.1.0]hexanes Catalyzed by Rhodium and Benzoic Acid.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7627
_journal_page_last               7630
_journal_paper_doi               10.1021/ja504048u
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H27 Br O4'
_chemical_formula_sum            'C30 H27 Br O4'
_chemical_formula_weight         531.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.0370(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.27530(10)
_cell_length_b                   7.74730(10)
_cell_length_c                   22.6981(4)
_cell_measurement_reflns_used    21621
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      3.90
_cell_volume                     1276.18(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22766
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    2.468
_exptl_absorpt_correction_T_max  0.373
_exptl_absorpt_correction_T_min  0.249
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881.  1935 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.04(1)
_refine_ls_extinction_coef       0.0501(11)
_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   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4460
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                4316
_reflns_number_total             4460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja504048u_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 4121832.cif.'
_cod_database_code               4121832