Hexafluoroisobutylation of enolates through a tandem elimination/allylic shift/hydrofluorination reaction
Delamare, Aline; Naulet, Guillaume; Kauffmann, Brice; Guichard, Gilles; Compain, Guillaume; Chemical Science 13 (2022) 9507–9514; doi:10.1039/D2SC02871A

data_1567477
_publ_section_title
;
 Hexafluoroisobutylation of enolates through a tandem elimination/allylic
 shift/hydrofluorination reaction
;
_journal_issue                   33
_journal_name_full               'Chemical Science'
_journal_page_first              9507
_journal_page_last               9514
_journal_paper_doi               10.1039/D2SC02871A
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C8 H8 F6 O2'
_chemical_formula_sum            'C8 H8 F6 O2'
_chemical_formula_weight         250.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-26 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.361(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2917(4)
_cell_length_b                   16.6360(10)
_cell_length_c                   9.1660(7)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    145
_cell_measurement_theta_max      72.2770
_cell_measurement_theta_min      5.3360
_cell_volume                     937.15(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      145
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.971
_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   -126.00 -15.00   1.00    1.00    --  -36.30  55.00-120.00  111
  2  \w   -104.00 -28.00   1.00    1.00    --  -36.30  28.00-150.00   76
  3  \w   -126.00 -86.00   1.00    1.00    --  -36.30  55.00-180.00   40
  4  \w     26.00  51.00   1.00    1.00    --  -36.30  55.00-120.00   25
  5  \w    -42.00  52.00   1.00    1.00    --  -36.30  55.00-180.00   94
  6  \w   -159.00-132.00   1.00    2.00    -- -110.00   9.00-180.00   27
  7  \w    -57.00 -21.00   1.00    2.00    -- -110.00  55.00-156.20   36
  8  \w   -178.00-140.00   1.00    2.00    -- -110.00  55.00-156.20   38
  9  \w    -90.00 -61.00   1.00    2.00    -- -110.00  55.00-156.20   29
 10  \w    -74.00 -48.00   1.00    2.00    -- -110.00   9.00-120.00   26
 11  \w   -198.00 -22.00   1.00    2.00    -- -110.00  55.00-105.99  176
 12  \w   -158.00 -78.00   1.00    2.00    -- -110.00   9.00-120.00   80
 13  \w   -133.00 -96.00   1.00    2.00    -- -110.00  55.00-156.20   37
 14  \w    -93.00 -22.00   1.00    2.00    -- -110.00  54.00 -54.60   71
 15  \w   -111.00 -65.00   1.00    2.00    -- -110.00   9.00-180.00   46
 16  \w   -161.00-114.00   1.00    2.00    -- -110.00  54.00 -54.60   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku FRX'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0621070000
_diffrn_orient_matrix_UB_12      0.0884831000
_diffrn_orient_matrix_UB_13      -0.0370412000
_diffrn_orient_matrix_UB_21      -0.2420413000
_diffrn_orient_matrix_UB_22      -0.0236507000
_diffrn_orient_matrix_UB_23      -0.0402080000
_diffrn_orient_matrix_UB_31      -0.0174820000
_diffrn_orient_matrix_UB_32      0.0141751000
_diffrn_orient_matrix_UB_33      0.1631022000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1849
_diffrn_reflns_point_group_measured_fraction_full 0.624
_diffrn_reflns_point_group_measured_fraction_max 0.609
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.400
_diffrn_reflns_theta_min         5.318
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1125
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0552
_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^)+(0.1369P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.247
_reflns_Friedel_fraction_full    0.259
_reflns_Friedel_fraction_max     0.243
_reflns_number_gt                1113
_reflns_number_total             1125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02871a2.cif
_cod_data_source_block           gc_x1
_cod_depositor_comments
'Adding full bibliography for 1567476--1567479.cif.'
_cod_original_cell_volume        937.15(12)
_cod_database_code               1567477
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C014(H014), C015(H015)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C011(H01A,H01B), C016(H01C,H01D)
;
_shelx_res_checksum              94591
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 5.283
_oxdiff_exptl_absorpt_empirical_full_min 0.396