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_4132887
_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            'C25 H27 Br2 N O3'
_chemical_formula_weight         549.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.298(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5365(10)
_cell_length_b                   9.5132(10)
_cell_length_c                   12.9888(14)
_cell_measurement_reflns_used    2310
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.931
_cell_measurement_theta_min      5.008
_cell_volume                     1168.8(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7114
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.153
_exptl_absorpt_coefficient_mu    3.494
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 1423 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.013(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0439P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                3626
_reflns_number_total             4401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07125_si_003.cif
_cod_data_source_block           cd214548
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132887
_shelxl_version_number           2013-4
_shelx_res_checksum              98026
_shelx_hkl_checksum              52687