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

data_7159146
_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 H24 O5'
_chemical_formula_sum            'C23 H24 O5'
_chemical_formula_weight         380.42
_chemical_name_common            4K
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-11
_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                102.2020(10)
_cell_angle_beta                 91.5720(10)
_cell_angle_gamma                100.0760(10)
_cell_formula_units_Z            2
_cell_length_a                   9.14550(10)
_cell_length_b                   9.46920(10)
_cell_length_c                   11.22560(10)
_cell_measurement_reflns_used    19427
_cell_measurement_temperature    103.8(3)
_cell_measurement_theta_max      76.3590
_cell_measurement_theta_min      4.0130
_cell_volume                     933.428(17)
_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      103.8(3)
_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 0.989
_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   -115.00 -59.00   0.50    1.00    --  -41.70-152.00  72.00  112
  2  \w    -85.00  -2.00   0.50    1.00    --  -41.70 121.00 -44.00  166
  3  \w   -105.00 -20.00   0.50    1.00    --  -41.70 152.00 115.00  170
  4  \w     24.00  95.00   0.50    1.00    --   41.70-121.00-127.00  142
  5  \w     41.00 115.00   0.50    1.00    --   41.70-152.00  72.00  148
  6  \w     41.00 131.00   0.50    4.00    --  112.00-152.00  72.00  180
  7  \w     38.00 111.00   0.50    4.00    --  112.00-121.00-127.00  146
  8  \w     99.00 178.00   0.50    4.00    --  112.00 121.00 -44.00  158
  9  \w     81.00 164.00   0.50    4.00    --  112.00 152.00 115.00  166
 10  \w      2.00  30.00   0.50    1.00    --   38.00  88.00 127.64   56
 11  \w   -115.00 -14.00   0.50    1.00    --  -41.70 -57.00-150.00  202
 12  \w   -116.00 -17.00   0.50    1.00    --  -41.70 -37.00 -30.00  198
 13  \w     27.00  98.00   0.50    1.00    --   41.70-125.00-180.00  142
 14  \w     13.00  42.00   0.50    1.00    --   46.00  80.00-131.90   58
 15  \w     13.00  42.00   0.50    1.00    --   46.00  80.00 -54.49   58
 16  \w     16.00  42.00   0.50    1.00    --   50.00  82.00  88.04   52
 17  \w     16.00  42.00   0.50    1.00    --   50.00  81.00 -45.13   52
 18  \w     16.00  42.00   0.50    1.00    --   50.00  82.00  23.38   52
 19  \w     16.00  42.00   0.50    1.00    --   50.00  82.00 158.60   52
 20  \w     30.00 130.00   0.50    1.00    --   58.00  55.00-105.43  200
 21  \w     31.00 136.00   0.50    1.00    --   62.00  71.00 165.32  210
 22  \w     32.00 135.00   0.50    1.00    --   62.00  64.00 105.71  206
 23  \w     35.00 139.00   0.50    1.00    --   66.00  69.00 -15.23  208
 24  \w     35.00 140.00   0.50    1.00    --   66.00  70.00  60.32  210
 25  \w     36.00 139.00   0.50    1.00    --   66.00  64.00-162.54  206
 26  \w     39.00 143.00   0.50    1.00    --   70.00  69.00 126.64  208
 27  \w     40.00 143.00   0.50    1.00    --   70.00  65.00 -99.37  206
 28  \w     39.00 143.00   0.50    1.00    --   70.00  69.00 115.11  208
 29  \w     43.00 148.00   0.50    1.00    --   74.00  71.00 -62.08  210
 30  \w     43.00 147.00   0.50    1.00    --   74.00  69.00  15.56  208
 31  \w     57.00 156.00   0.50    4.00    --   82.00  42.00  10.83  198
 32  \w     52.00 155.00   0.50    4.00    --   82.00  64.00 -69.18  206
 33  \w     54.00 154.00   0.50    4.00    --   82.00  54.00  76.19  200
 34  \w     51.00 156.00   0.50    4.00    --   82.00  71.00 132.47  210
 35  \w     65.00 167.00   0.50    4.00    --   94.00  60.00-153.45  204
 36  \w     83.00 178.00   0.50    4.00    --  112.00  61.00-120.00  190
 37  \w     36.00 145.00   0.50    4.00    --  112.00 -77.00-150.00  218
 38  \w     83.00 178.00   0.50    4.00    --  112.00  61.00   0.00  190
 39  \w     83.00 178.00   0.50    4.00    --  112.00  61.00-150.00  190
 40  \w     36.00 109.00   0.50    4.00    --  112.00-111.00  60.00  146
 41  \w     36.00 140.00   0.50    4.00    --  112.00 -30.00-180.00  208
 42  \w     29.00 107.00   0.50    4.00    --  112.00 -94.00-120.00  156
 43  \w     83.00 178.00   0.50    4.00    --  112.00  61.00 -60.00  190
 44  \w    104.00 178.00   0.50    4.00    --  112.00 111.00  60.00  148
 45  \w     83.00 178.00   0.50    4.00    --  112.00  61.00 -90.00  190
 46  \w     83.00 178.00   0.50    4.00    --  112.00  61.00 120.00  190
 47  \w     83.00 178.00   0.50    4.00    --  112.00  61.00-180.00  190
 48  \w     86.00 178.00   0.50    4.00    --  112.00  45.00 150.00  184
 49  \w     39.00 109.00   0.50    4.00    --  112.00-111.00-150.00  140
 50  \w    144.00 170.00   0.50    4.00    --  112.00  61.00 150.00   52
 51  \w     42.00  86.00   0.50    4.00    --  112.00-111.00-180.00   88
 52  \w     84.00 136.00   0.50    4.00    --  112.00  61.00 150.00  104
 53  \w     79.00 119.00   0.50    4.00    --  112.00 -61.00  30.00   80
 54  \w     83.00 178.00   0.50    4.00    --  112.00  61.00  90.00  190
 55  \w     83.00 177.00   0.50    4.00    --  112.00  61.00  30.00  188
 56  \w     30.00 106.00   0.50    4.00    --  112.00 -94.00 120.00  152
 57  \w     83.00 140.00   0.50    4.00    --  112.00  64.00-143.07  114
 58  \w    129.00 163.00   0.50    4.00    --  112.00  61.00 -30.00   68
 59  \w     37.00 108.00   0.50    4.00    --  112.00-111.00  90.00  142
 60  \w     83.00 118.00   0.50    4.00    --  112.00  61.00 -30.00   70
 61  \w     83.00 161.00   0.50    4.00    --  112.00  61.00  60.00  156
;
_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      -0.0637725000
_diffrn_orient_matrix_UB_12      -0.1593142000
_diffrn_orient_matrix_UB_13      0.0076845000
_diffrn_orient_matrix_UB_21      -0.0324451000
_diffrn_orient_matrix_UB_22      -0.0418585000
_diffrn_orient_matrix_UB_23      -0.1396502000
_diffrn_orient_matrix_UB_31      0.1558319000
_diffrn_orient_matrix_UB_32      -0.0394333000
_diffrn_orient_matrix_UB_33      -0.0155656000
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28164
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.358
_diffrn_reflns_theta_min         4.038
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_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            'clear pale colourless'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0514P)^2^+0.2750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3555
_reflns_number_total             3882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00122a2.cif
_cod_data_source_block           bau45
_cod_depositor_comments
'Adding full bibliography for 7159144--7159146.cif.'
_cod_database_code               7159146
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H24O5
_chemical_oxdiff_usercomment     'Compound 4K, Bau45'
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.893
_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:
 C7(H7A,H7B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C6(H6), C3(H3), C2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              30775
_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.910