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_4035424
_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            'C41 H34 O2 P2'
_chemical_formula_weight         620.62
_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                 105.650(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2427(17)
_cell_length_b                   27.713(5)
_cell_length_c                   12.453(2)
_cell_measurement_reflns_used    3486
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.74
_cell_measurement_theta_min      2.19
_cell_volume                     3403.8(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24791
_diffrn_reflns_point_group_measured_fraction_full 0.811
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         1.698
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 1851 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     815
_refine_ls_number_reflns         12409
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0706P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.570
_reflns_Friedel_fraction_full    0.617
_reflns_Friedel_fraction_max     0.588
_reflns_number_gt                6902
_reflns_number_total             12409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01693_si_003.cif
_cod_data_source_block           mo_61223a
_cod_original_cell_volume        3403.7(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035424
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.923
_shelx_res_checksum              85062
_shelx_hkl_checksum              46011