Exploration of chiral diastereomeric spiroketal (SPIROL)-based phosphinite ligands in asymmetric hydrogenation of heterocycles.
Sun, Siyuan; Nagorny, Pavel; Chemical communications (Cambridge, England) 56 (2020) 8432–8435; doi:10.1039/d0cc03088k

data_7126761
_publ_section_title
;
 Exploration of chiral diastereomeric spiroketal (SPIROL)-based
 phosphinite ligands in asymmetric hydrogenation of heterocycles.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8432
_journal_page_last               8435
_journal_paper_doi               10.1039/d0cc03088k
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 O4'
_chemical_formula_sum            'C19 H20 O4'
_chemical_formula_weight         312.35
_chemical_name_common            (S,S,S)-SPIROL
_chemical_name_systematic
(1S,3S,3'S)-3,3'-diethyl-3H,3'H-1,1'-spirobi[isobenzofuran]-7,7'-diol
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-02-24 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   12.81980(10)
_cell_length_b                   12.81980(10)
_cell_length_c                   27.9907(5)
_cell_measurement_reflns_used    33076
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      69.0340
_cell_measurement_theta_min      3.1490
_cell_volume                     3983.89(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            61312
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.164
_diffrn_reflns_theta_min         3.982
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1494
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
; 
 Flack x determined using 2032 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 

 Bayesian Statistics                       
 Student_T Nu       13                                  
 Select Pairs     2123                              
 Theta_Min ..     6.91                                    
 Theta_Max ..    69.01                        
 P2(true)....    1.000                
 P3(true)....    1.000                               
 P3(rac-twin)  0.8E-40                        
 P3(false) ..  0.2-129                            
 G ..........   1.2271                         
 G (su) .....   0.0876                                       
 Hooft y .... -0.11(4)                         
 
;
_refine_ls_abs_structure_Flack   -0.11(6)
_refine_ls_extinction_coef       0.0043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0880P)^2^+0.4027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4874
_reflns_number_total             4949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03088k2.cif
_cod_data_source_block           ssspiro
_cod_depositor_comments          'Adding full bibliography for 7126761.cif.'
_cod_original_cell_volume        3983.88(9)
_cod_database_code               7126761
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.890
_shelx_res_checksum              20487