Enantioselective synthesis of C2 -symmetric spirobipyridine ligands through cationic Rh(I)/modified-BINAP- catalyzed double [2 + 2 + 2] cycloaddition.
Wada, Azusa; Noguchi, Keiichi; Hirano, Masao; Tanaka, Ken; Organic letters 9 (2007) 1295–1298; doi:10.1021/ol070129e

data_1505336
_publ_section_title
;
 Enantioselective synthesis of C2 -symmetric spirobipyridine ligands
 through cationic Rh(I)/modified-BINAP- catalyzed double [2 + 2 + 2]
 cycloaddition.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1295
_journal_page_last               1298
_journal_paper_doi               10.1021/ol070129e
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H24 Cl2 N2 O2'
_chemical_formula_sum            'C31 H24 Cl2 N2 O2'
_chemical_formula_weight         527.42
_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
_audit_creation_date             2006-12-19
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.939(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   21.612(2)
_cell_length_b                   5.5038(6)
_cell_length_c                   11.8718(12)
_cell_measurement_reflns_used    10246
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.4
_cell_volume                     1198.3(2)
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10456
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    2.711
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.596
_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    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 865 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.001(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2096
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.3839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                1993
_reflns_number_total             2096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070129esi20070119_113756.cif
_cod_data_source_block           global
_cod_original_cell_volume        1198.4(2)
_cod_database_code               1505336