Chiral Cyclohexyl-Fused Spirobiindanes: Practical Synthesis, Ligand Development, and Asymmetric Catalysis.
Zheng, Zhiyao; Cao, Yuxi; Chong, Qinglei; Han, Zhaobin; Ding, Jiaming; Luo, Chenguang; Wang, Zheng; Zhu, Dongsheng; Zhou, Qi-Lin; Ding, Kuiling; Journal of the American Chemical Society 140 (2018) 10374–10381; doi:10.1021/jacs.8b07125

data_4132888
_publ_section_title
;
 Chiral Cyclohexyl-Fused Spirobiindanes: Practical Synthesis, Ligand
 Development, and Asymmetric Catalysis.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10374
_journal_page_last               10381
_journal_paper_doi               10.1021/jacs.8b07125
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36 H36 N O2 P'
_chemical_formula_weight         545.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5285(15)
_cell_length_b                   14.1892(18)
_cell_length_c                   18.146(2)
_cell_measurement_reflns_used    3340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.879
_cell_measurement_theta_min      4.489
_cell_volume                     2968.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16449
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.822
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 1579 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.0718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1306
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4243
_reflns_number_total             5239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07125_si_006.cif
_cod_data_source_block           cd17138
_cod_original_cell_volume        2968.3(7)
_cod_database_code               4132888
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2013-4
_shelx_res_checksum              63137
_shelx_hkl_checksum              72201