Practical enantioselective synthesis of axially chiral biaryl diphosphonates and dicarboxylates by cationic rhodium(I)/Segphos-catalyzed double [2 + 2 + 2] cycloaddition.
Nishida, Goushi; Ogaki, Shuichiro; Yusa, Yukinori; Yokozawa, Tohru; Noguchi, Keiichi; Tanaka, Ken; Organic letters 10 (2008) 2849–2852; doi:10.1021/ol801013v

data_1504745
_publ_section_title
;
 Practical enantioselective synthesis of axially chiral biaryl
 diphosphonates and dicarboxylates by cationic
 rhodium(I)/Segphos-catalyzed double [2 + 2 + 2] cycloaddition.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2849
_journal_page_last               2852
_journal_paper_doi               10.1021/ol801013v
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H48 Br2 N2 O10 P2 S2, C3 H6 O'
_chemical_formula_sum            'C43 H54 Br2 N2 O11 P2 S2'
_chemical_formula_weight         1060.76
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.2078(3)
_cell_length_b                   11.5303(2)
_cell_length_c                   12.0049(2)
_cell_measurement_reflns_used    20855
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.8
_cell_volume                     2325.33(7)
_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
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21228
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    4.205
_exptl_absorpt_correction_T_max  0.279
_exptl_absorpt_correction_T_min  0.121
_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    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881  2004 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4252
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0482
_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^)+(0.1041P)^2^+2.7983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                4051
_reflns_number_total             4252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801013v-file005.cif
_cod_data_source_block           I
_cod_original_cell_volume        2325.32(7)
_cod_database_code               1504745