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_1567478
_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_absolute_configuration ad
_chemical_formula_moiety         'C31 H25 F7 N3 Ni O3'
_chemical_formula_sum            'C31 H25 F7 N3 Ni O3'
_chemical_formula_weight         679.25
_chemical_name_systematic        gc79b1f2
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-02-26 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.02050(10)
_cell_length_b                   13.91850(10)
_cell_length_c                   19.0776(2)
_cell_measurement_reflns_used    20111
_cell_measurement_temperature    130
_cell_measurement_theta_max      73.6070
_cell_measurement_theta_min      2.3130
_cell_volume                     2926.29(5)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku FRX'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19975
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.987
_diffrn_reflns_theta_min         3.931
_exptl_absorpt_coefficient_mu    1.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2478 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(12)
_refine_ls_extinction_coef       0.00249(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+1.7095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5836
_reflns_number_total             5879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02871a2.cif
_cod_data_source_block           gc_79b1_f2_ap_a
_cod_depositor_comments
'Adding full bibliography for 1567476--1567479.cif.'
_cod_database_code               1567478
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.848
_shelx_estimated_absorpt_t_min   0.848
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: F0D(0.75) F1(0.25)
3.a Ternary CH refined with riding coordinates:
 C00I(H00I), C00U(H00U), C010(H010)
3.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00Y(H00C,H00D), C00Z(H00E,H00F), C014(H01A,H01B), C016(H01C,
 H01D)
3.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00L(H00L), C00P(H00P), C00S(H00S), C00W(H00W),
 C00X(H00X), C012(H012), C013(H013), C015(H015), C018(H018), C019(H019)
;
_shelx_res_checksum              78385
_olex2_submission_original_sample_id gc79b1f2
_olex2_submission_special_instructions 'No special instructions were received'