Visible-light-induced difunctionalization of β-CF<sub>2</sub>H-1,3-enynes to access CF<sub>2</sub>H-containing all-carbon quaternary centers.
Chen, Shu-Jie; Lin, Jin-Hao; Wu, Jia-Ming; Li, You-Hong; Dong, Bao-Le; Chen, Guo-Shu; Liu, Yun-Lin; Organic & biomolecular chemistry 23 (2025) 4069–4073; doi:10.1039/d5ob00425j

data_7160469
_publ_section_title
;
 Visible-light-induced difunctionalization of
 &#x3b2;-CF<sub>2</sub>H-1,3-enynes to access CF<sub>2</sub>H-containing
 all-carbon quaternary centers.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4069
_journal_page_last               4073
_journal_paper_doi               10.1039/d5ob00425j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C27 H34 Cl F2 N O Si'
_chemical_formula_sum            'C27 H34 Cl F2 N O Si'
_chemical_formula_weight         490.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-08-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-22 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                76.468(3)
_cell_angle_beta                 76.054(3)
_cell_angle_gamma                81.669(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4228(3)
_cell_length_b                   12.3770(4)
_cell_length_c                   15.3766(5)
_cell_measurement_reflns_used    7799
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.1190
_cell_measurement_theta_min      2.4100
_cell_volume                     1327.10(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -76.00  20.00   1.00    1.45    --  -11.27 -77.00-150.00   96
  2  \w    -58.00  36.00   1.00    1.45    --   11.90 -57.00 -30.00   94
  3  \w    -15.00  80.00   1.00    1.45    --   11.90  57.00 120.00   95
  4  \w    -69.00 -26.00   1.00    1.45    --  -11.27 127.00-108.84   43
  5  \w    -88.00 -51.00   1.00    1.45    --  -11.27 155.00  -0.48   37
  6  \w    -68.00  75.00   1.00    1.45    --   11.90   0.00  30.00  143
  7  \w    -15.00  27.00   1.00    1.45    --   11.90 -99.00-120.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0755717000
_diffrn_orient_matrix_UB_12      -0.0296077000
_diffrn_orient_matrix_UB_13      0.0189487000
_diffrn_orient_matrix_UB_21      -0.0592830000
_diffrn_orient_matrix_UB_22      -0.0408105000
_diffrn_orient_matrix_UB_23      0.0276245000
_diffrn_orient_matrix_UB_31      0.0235533000
_diffrn_orient_matrix_UB_32      -0.0310348000
_diffrn_orient_matrix_UB_33      -0.0351893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18104
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.399
_diffrn_reflns_theta_min         1.963
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         6397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0900P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4950
_reflns_number_total             7313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00425j2.cif
_cod_data_source_block           0907
_cod_depositor_comments          'Adding full bibliography for 7160469.cif.'
_cod_database_code               7160469
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19), C25(H25), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C23(H23A,H23B,
 H23C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              49167
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 118.460
_oxdiff_exptl_absorpt_empirical_full_min 0.511