Development of Immobilized SPINOL-Derived Chiral Phosphoric Acids for Catalytic Continuous Flow Processes. Use in the Catalytic Desymmetrization of 3,3-Disubstituted Oxetanes
Lai, Junshan; Fianchini, Mauro; Pericàs, Miquel A.; ACS Catalysis  (2020) 14971–14983; doi:10.1021/acscatal.0c04497

data_4518293
_publ_section_title
;
 Development of Immobilized SPINOL-Derived Chiral Phosphoric Acids for
 Catalytic Continuous Flow Processes. Use in the Catalytic
 Desymmetrization of 3,3-Disubstituted Oxetanes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14971
_journal_page_last               14983
_journal_paper_doi               10.1021/acscatal.0c04497
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C79 H45.5 Br2 F6 I2 O10'
_chemical_formula_weight         1682.27
_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-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.1331(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5988(4)
_cell_length_b                   13.7054(3)
_cell_length_c                   26.5064(4)
_cell_measurement_reflns_used    43588
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8210
_cell_measurement_theta_min      2.2500
_cell_volume                     6552.1(2)
_computing_cell_refinement
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_data_collection
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_data_reduction
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_molecular_graphics
'shelXle (H&#x00FC;bschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    Sir2019
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            52522
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.786
_diffrn_reflns_theta_min         2.258
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    2.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       Plate
_exptl_crystal_F_000             3318
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.388
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 9552 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2003
_refine_ls_number_reflns         52522
_refine_ls_number_restraints     755
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0676
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                36577
_reflns_number_total             52522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04497_si_002.cif
_cod_data_source_block           JLAI0828_hklf5
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C79 H45.50 Br2 F6 I2 O10'
_cod_database_code               4518293
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.602
_shelx_estimated_absorpt_t_max   0.895
_shelx_res_checksum              18507
_shelx_hkl_checksum              35351