Carbene-controlled regioselectivity in photochemical cascades.
Di Filippo, Mara; Baumann, Marcus; Organic & biomolecular chemistry 21 (2023) 2930–2934; doi:10.1039/d3ob00122a

data_7159145
_publ_section_title
;
 Carbene-controlled regioselectivity in photochemical cascades.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2930
_journal_page_last               2934
_journal_paper_doi               10.1039/d3ob00122a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H21 F O4'
_chemical_formula_sum            'C23 H21 F O4'
_chemical_formula_weight         380.40
_chemical_name_common            4J
_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     dual
_audit_creation_date             2022-06-10
_audit_creation_method
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_audit_update_record
;
2022-08-15 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                86.328(2)
_cell_angle_beta                 76.801(3)
_cell_angle_gamma                87.255(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6257(3)
_cell_length_b                   10.2667(3)
_cell_length_c                   10.6007(3)
_cell_measurement_reflns_used    6698
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      75.1250
_cell_measurement_theta_min      4.2610
_cell_volume                     911.56(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -80.00  18.00   0.50    1.50    --  -41.58  97.00-132.00  196
  2  \w      4.00  81.00   0.50    1.50    --   41.58 -97.00 118.00  154
  3  \w     30.00 107.00   0.50    6.00    --  112.00 -97.00 118.00  154
  4  \w    104.00 178.00   0.50    6.00    --  112.00  97.00-132.00  148
  5  \w   -116.00 -17.00   0.50    1.50    --  -41.58 -37.00  90.00  198
  6  \w   -115.00 -13.00   0.50    1.50    --  -41.58 -57.00   0.00  204
  7  \w    -38.00  83.00   0.50    1.50    --   41.58 -19.00 -60.00  242
  8  \w      8.00  42.00   0.50    1.50    --   41.58  82.00 -34.88   68
  9  \w      8.00  42.00   0.50    1.50    --   41.58  82.00-125.10   68
 10  \w     86.00 178.00   0.50    6.00    --  112.00  45.00   0.00  184
 11  \w     84.00 178.00   0.50    6.00    --  112.00  30.00 -90.00  188
 12  \w     39.00 138.00   0.50    6.00    --  112.00 -45.00 120.00  198
 13  \w     84.00 178.00   0.50    6.00    --  112.00  30.00  60.00  188
 14  \w     36.00 145.00   0.50    6.00    --  112.00 -77.00  30.00  218
 15  \w     36.00 109.00   0.50    6.00    --  112.00-111.00   0.00  146
 16  \w     36.00 109.00   0.50    6.00    --  112.00-111.00-120.00  146
 17  \w    103.00 178.00   0.50    6.00    --  112.00  77.00  90.00  150
 18  \w     36.00 109.00   0.50    6.00    --  112.00-111.00 120.00  146
 19  \w     61.00 146.00   0.50    6.00    --  112.00 178.00  60.00  170
 20  \w     36.00 109.00   0.50    6.00    --  112.00-111.00-150.00  146
 21  \w     29.00 107.00   0.50    6.00    --  112.00 -94.00 -90.00  156
 22  \w     36.00 109.00   0.50    6.00    --  112.00-111.00  60.00  146
 23  \w     36.00 109.00   0.50    6.00    --  112.00-111.00  30.00  146
 24  \w    104.00 178.00   0.50    6.00    --  112.00 111.00-180.00  148
 25  \w    104.00 178.00   0.50    6.00    --  112.00 111.00 150.00  148
 26  \w     39.00 138.00   0.50    6.00    --  112.00 -45.00  90.00  198
 27  \w     29.00 107.00   0.50    6.00    --  112.00 -94.00 -60.00  156
 28  \w     86.00 178.00   0.50    6.00    --  112.00  45.00 150.00  184
 29  \w   -116.00 -17.00   0.50    1.50    --  -41.58 -37.00-120.00  198
 30  \w   -116.00 -17.00   0.50    1.50    --  -41.58 -37.00-180.00  198
 31  \w      8.00  42.00   0.50    1.50    --   41.58  80.00  38.52   68
 32  \w     27.00  98.00   0.50    1.50    --   41.58-125.00   0.00  142
 33  \w    -33.00  66.00   0.50    1.50    --   41.58 -37.00 120.00  198
 34  \w      8.00  42.00   0.50    1.50    --   41.58  82.00 130.33   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0455454000
_diffrn_orient_matrix_UB_12      -0.0611086000
_diffrn_orient_matrix_UB_13      0.1394672000
_diffrn_orient_matrix_UB_21      0.1651975000
_diffrn_orient_matrix_UB_22      -0.0697511000
_diffrn_orient_matrix_UB_23      -0.0191215000
_diffrn_orient_matrix_UB_31      0.0657873000
_diffrn_orient_matrix_UB_32      0.1184736000
_diffrn_orient_matrix_UB_33      0.0503117000
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14565
_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         76.397
_diffrn_reflns_theta_min         4.290
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark yellow'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0493P)^2^+0.1895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3052
_reflns_number_total             3765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00122a2.cif
_cod_data_source_block           bau47
_cod_depositor_comments
'Adding full bibliography for 7159144--7159146.cif.'
_cod_database_code               7159145
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         ' C23 H23 F1 O3'
_chemical_oxdiff_usercomment     'Compound 4J, Bau47'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.885
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              76934
_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 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.882