Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters
Jiang, Liyin; Sarró, Pau; Teo, Wei Jie; Llop, Jordi; Suero, Marcos; Chemical Science  (2022) –; doi:10.1039/D2SC00968D

data_1566612
_publ_section_title
;
 Catalytic alkene skeletal modification for the construction of
 fluorinated tertiary stereocenters
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00968D
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H39 F O4'
_chemical_formula_weight         434.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-06-28 deposited with the CCDC.	2022-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.281(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7648(15)
_cell_length_b                   6.0876(5)
_cell_length_c                   26.974(2)
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5220
_cell_measurement_theta_min      3.0440
_cell_volume                     2409.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_molecular_graphics
'shelXle (H\"ubschle, 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      100(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 0.893
_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_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8906
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.776
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.574
_diffrn_reflns_theta_min         2.776
_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    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69427
_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    1.198
_exptl_crystal_description       Block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1326 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0583P)^2^+1.8686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.827
_reflns_Friedel_fraction_max     0.637
_reflns_number_gt                3878
_reflns_number_total             4779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00968d2.cif
_cod_data_source_block           JLY-202101
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1566612
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              94387
_shelx_hkl_checksum              17485