Enantioselective Synthesis of Tetra-ortho-Substituted Axially Chiral Biaryls through Rhodium-Catalyzed Double [2 + 2 + 2] Cycloaddition.
Nishida, Goushi; Suzuki, Nanami; Noguchi, Keiichi; Tanaka, Ken; Organic letters 8 (2006) 3489–3492; doi:10.1021/ol0611550

data_1506097
_publ_section_title
;
 Enantioselective Synthesis of Tetra-ortho-Substituted Axially Chiral
 Biaryls through Rhodium-Catalyzed Double [2 + 2 + 2] Cycloaddition.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3489
_journal_page_last               3492
_journal_paper_doi               10.1021/ol0611550
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H34 O12 '
_chemical_formula_sum            'C32 H34 O12'
_chemical_formula_weight         610.61
_chemical_name_systematic
;
 6,6'-Bis-acetoxymethyl-2,3,2',3'-tetrahydro-1H,1'H-[5,5']biindenyl-
 4,7,4',7'-tetracarboxylic acid tetraethyl ester
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5522(6)
_cell_length_b                   13.1153(6)
_cell_length_c                   21.9409(11)
_cell_measurement_reflns_used    36184
_cell_measurement_temperature    223
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.4
_cell_volume                     3036.5(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics
'ORTEP-3 for Windows Ver. 1.076 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40292
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881  2410 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.04(18)
_refine_ls_extinction_coef       0.0013(2)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                4367
_reflns_number_total             5555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0611550si20060615_052210.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C32 H34 O12 '
_cod_database_code               1506097