Photo-induced energy transfer relay of N-heterocyclic carbene catalysis: an asymmetric α-fluorination/isomerization cascade.
Jiang, Xinhang; Li, En; Chen, Jiean; Huang, Yong; Chemical communications (Cambridge, England) 57 (2021) 729–732; doi:10.1039/d0cc07264h

data_7127567
_publ_section_title
;
 Photo-induced energy transfer relay of N-heterocyclic carbene catalysis:
 an asymmetric \a-fluorination/isomerization cascade.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              729
_journal_page_last               732
_journal_paper_doi               10.1039/d0cc07264h
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H19 F O2'
_chemical_formula_sum            'C27 H19 F O2'
_chemical_formula_weight         394.42
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-02
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.05.22 svn.r1d9e7f8d for OlexSys, GUI svn.r6115)
;
_audit_update_record
;
2020-06-03 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.545(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5867(11)
_cell_length_b                   4.3673(4)
_cell_length_c                   16.8442(12)
_cell_measurement_reflns_used    5162
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      74.0150
_cell_measurement_theta_min      2.6280
_cell_volume                     967.45(14)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_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   -114.00 -16.00   1.00    1.00    --  -39.98 -37.00-120.00   98
  2  \w   -112.00 -12.00   1.00    1.00    --  -39.98 -57.00  30.00  100
  3  \w    -68.00  33.00   1.00    1.00    --  -39.98  57.00-180.00  101
  4  \w   -114.00 -16.00   1.00    1.00    --  -39.98 -37.00  30.00   98
  5  \w   -112.00 -12.00   1.00    1.00    --  -39.98 -57.00 -60.00  100
  6  \w      7.00 116.00   1.00    1.00    --   39.98  77.00  60.00  109
  7  \w     16.00 114.00   1.00    1.00    --   39.98  37.00  60.00   98
  8  \w     23.00  96.00   1.00    1.00    --   39.98-125.00  90.00   73
  9  \w     76.00 178.00   1.00    2.73    --  108.20  77.00   0.00  102
 10  \w     79.00 178.00   1.00    2.73    --  108.20  61.00  30.00   99
 11  \w     76.00 178.00   1.00    2.73    --  108.20  77.00  30.00  102
 12  \w     82.00 178.00   1.00    2.73    --  108.20  45.00 -60.00   96
 13  \w     83.00 117.00   1.00    2.73    --  108.20  45.00  30.00   34
 14  \w     80.00 108.00   1.00    2.73    --  108.20  77.00 -30.00   28
 15  \w     79.00 106.00   1.00    2.73    --  108.20  61.00 -60.00   27
 16  \w    139.00 176.00   1.00    2.73    --  108.20  61.00 -30.00   37
 17  \w     80.00 108.00   1.00    2.73    --  108.20  61.00 -30.00   28
 18  \w     84.00 112.00   1.00    2.73    --  108.20  45.00 -90.00   28
 19  \w     79.00 105.00   1.00    2.73    --  108.20  61.00 -90.00   26
 20  \w     79.00 107.00   1.00    2.73    --  108.20  61.00   0.00   28
 21  \w     72.00 116.00   1.00    2.73    --  108.20-125.00  60.00   44
 22  \w     36.00  61.00   1.00    2.73    --  108.20-125.00  60.00   25
 23  \w     78.00 106.00   1.00    2.73    --  108.20  77.00 -60.00   28
 24  \w    125.00 178.00   1.00    2.73    --  108.20  77.00 -60.00   53
 25  \w     53.00  97.00   1.00    2.73    --  108.20 -94.00  90.00   44
 26  \w     82.00 110.00   1.00    2.73    --  108.20  45.00   0.00   28
 27  \w    131.00 176.00   1.00    2.73    --  108.20  77.00 -90.00   45
 28  \w     83.00 108.00   1.00    2.73    --  108.20  45.00  60.00   25
 29  \w     80.00 108.00   1.00    2.73    --  108.20  30.00   0.00   28
 30  \w     76.00 102.00   1.00    2.73    --  108.20  77.00 -90.00   26
 31  \w     26.00 102.00   1.00    2.73    --  108.20 -94.00   0.00   76
 32  \w     85.00 119.00   1.00    2.73    --  108.20  30.00 -30.00   34
 33  \w     83.00 112.00   1.00    2.73    --  108.20  30.00  30.00   29
 34  \w     77.00 105.00   1.00    2.73    --  108.20  77.00-120.00   28
 35  \w    111.00 171.00   1.00    2.73    --  108.20  77.00-120.00   60
 36  \w     83.00 111.00   1.00    2.73    --  108.20  45.00 -30.00   28
 37  \w     40.00  66.00   1.00    1.00    --   41.23  37.00  30.00   26
 38  \w     25.00  52.00   1.00    1.00    --   41.23  77.00  60.00   27
 39  \w     81.00 106.00   1.00    2.73    --  106.95  45.00 -90.00   25
 40  \w     85.00 111.00   1.00    2.73    --  106.95  30.00 -60.00   26
 41  \w     74.00 100.00   1.00    2.73    --  106.95  77.00 -30.00   26
 42  \w     82.00 108.00   1.00    2.73    --  106.95  45.00  30.00   26
 43  \w     78.00 104.00   1.00    2.73    --  106.95  61.00  30.00   26
 44  \w     79.00 105.00   1.00    2.73    --  106.95  61.00 -30.00   26
 45  \w     74.00 100.00   1.00    2.73    --  106.95  77.00-120.00   26
;
_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      0.1061136000
_diffrn_orient_matrix_UB_12      0.0767777000
_diffrn_orient_matrix_UB_13      -0.0118030000
_diffrn_orient_matrix_UB_21      -0.0405488000
_diffrn_orient_matrix_UB_22      -0.0410906000
_diffrn_orient_matrix_UB_23      -0.0933546000
_diffrn_orient_matrix_UB_31      -0.0285197000
_diffrn_orient_matrix_UB_32      0.3418822000
_diffrn_orient_matrix_UB_33      -0.0085175000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3636
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.709
_diffrn_reflns_theta_min         2.710
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62625
_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    1.354
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Flack x determined using 1173 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0973
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1418P)^2^+2.7019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2945
_refine_ls_wR_factor_ref         0.2962
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                3445
_reflns_number_total             3636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07264h2.cif
_cod_data_source_block           exp_2153
_cod_depositor_comments          'Adding full bibliography for 7127567.cif.'
_cod_database_code               7127567
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.712(3)
 0.288(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              65388
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.568