Asymmetric synthesis of axially chiral biaryl diphosphine ligands by rhodium-catalyzed enantioselective intramolecular double [2 + 2 + 2] cycloaddition.
Mori, Fumiya; Fukawa, Naohiro; Noguchi, Keiichi; Tanaka, Ken; Organic letters 13 (2011) 362–365; doi:10.1021/ol102927y

data_1501930
_publ_section_title
;
 Asymmetric synthesis of axially chiral biaryl diphosphine ligands by
 rhodium-catalyzed enantioselective intramolecular double [2 + 2 + 2]
 cycloaddition.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              362
_journal_page_last               365
_journal_paper_doi               10.1021/ol102927y
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C44 H36 O4 P2'
_chemical_formula_sum            'C44 H36 O4 P2'
_chemical_formula_weight         690.67
_chemical_name_systematic
;
  (R)-5,5'-Bis(diphenylphosphanyl)-1,3,6,8,1',3',6',8'-octahydro-
  [4,4']bi[2,7-dioxaasindacenyl]
;
_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   geom
_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                   8.98499(16)
_cell_length_b                   16.8485(3)
_cell_length_c                   23.4132(4)
_cell_measurement_reflns_used    63276
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.2
_cell_volume                     3544.37(11)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            66960
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    1.464
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.365
_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    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881.  2812 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.014(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0569P)^2^+0.4792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0826
_reflns_number_gt                6352
_reflns_number_total             6446
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102927y_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        3544.38(11)
_cod_database_code               1501930