Asymmetric Synthesis of Chiral Spiroketal Bisphosphine Ligands and Their Application in Enantioselective Olefin Hydrogenation.
Huang, Jian; Hong, Mao; Wang, Chuan-Chuan; Kramer, Søren; Lin, Guo-Qiang; Sun, Xing-Wen; The Journal of organic chemistry 83 (2018) 12838–12846; doi:10.1021/acs.joc.8b01693

data_4035423
_publ_section_title
;
 Asymmetric Synthesis of Chiral Spiroketal Bisphosphine Ligands and Their
 Application in Enantioselective Olefin Hydrogenation.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12838
_journal_page_last               12846
_journal_paper_doi               10.1021/acs.joc.8b01693
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C40 H32 O2 P2'
_chemical_formula_weight         606.59
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.249(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.283(5)
_cell_length_b                   8.734(4)
_cell_length_c                   16.552(8)
_cell_measurement_reflns_used    904
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.515
_cell_measurement_theta_min      2.463
_cell_volume                     1629.9(13)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_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  0.0410
_diffrn_reflns_av_unetI/netI     0.1199
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7780
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         1.806
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 975 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6275
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.889
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                3052
_reflns_number_total             6275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01693_si_004.cif
_cod_data_source_block           a61123a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035423
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.906
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              97598
_shelx_hkl_checksum              4807