Enantioselective catalytic remote perfluoroalkylation of α-branched enals driven by light.
Balletti, Matteo; Wachsmuth, Tommy; Di Sabato, Antonio; Hartley, Will C.; Melchiorre, Paolo; Chemical science 14 (2023) 4923–4927; doi:10.1039/d3sc01347b

data_1568865
_publ_section_title
;
 Enantioselective catalytic remote perfluoroalkylation of &#x3b1;-branched
 enals driven by light.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              4923
_journal_page_last               4927
_journal_paper_doi               10.1039/d3sc01347b
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H11 F21 O'
_chemical_formula_weight         678.30
_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
_audit_update_record
;
2022-10-25 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.285(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6498(2)
_cell_length_b                   9.6522(3)
_cell_length_c                   22.2488(6)
_cell_measurement_reflns_used    8532
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.64
_cell_measurement_theta_min      3.98
_cell_volume                     1212.33(7)
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_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    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14295
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.986
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.65
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_description       plate
_exptl_crystal_F_000             668
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and diethyl ether'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0624P)^2^+0.8294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                3926
_reflns_number_total             4183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01347b2.cif
_cod_data_source_block           cu_WCH-xray-B_0m
_cod_depositor_comments          'Adding full bibliography for 1568865.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1568865
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.818
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              61087