Construction of fused heterocycles by visible-light induced dearomatization of nonactivated arenes.
Liu, Tianyu; Luo, Yong; Liu, Yidong; Organic & biomolecular chemistry 22 (2024) 9179–9183; doi:10.1039/d4ob01530d

data_7160190
_publ_section_title
;
 Construction of fused heterocycles by visible-light induced
 dearomatization of nonactivated arenes.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9179
_journal_page_last               9183
_journal_paper_doi               10.1039/d4ob01530d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C54 H42 O2'
_chemical_formula_sum            'C54 H42 O2'
_chemical_formula_weight         722.87
_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             2023-02-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2023-03-19 deposited with the CCDC.	2024-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                94.895(2)
_cell_angle_beta                 102.914(2)
_cell_angle_gamma                109.561(3)
_cell_formula_units_Z            2
_cell_length_a                   11.1157(4)
_cell_length_b                   12.0628(5)
_cell_length_c                   16.2649(4)
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5890
_cell_measurement_theta_min      2.8100
_cell_volume                     1972.37(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -15.00  11.00   1.00    1.00    --    0.00 -57.00-150.00   26
  2  \w     10.00  40.00   1.00    1.00    --    0.00  77.00   0.00   30
  3  \w    -28.00   5.00   1.00    1.00    --    0.00  77.00   0.00   33
  4  \w    -69.00 -28.00   1.00    1.00    --    0.00 -57.00-150.00   41
  5  \w     37.00 110.00   1.00    2.11    --   54.00-125.00-180.00   73
  6  \w     -9.00  68.00   1.00    2.11    --   54.00 -57.00   0.00   77
  7  \w     23.00  69.00   1.00    2.11    --   54.00-125.00   0.00   46
  8  \w     29.00 116.00   1.00    2.11    --   54.00  77.00-150.00   87
  9  \w     10.00 127.00   1.00    2.11    --   54.00  19.00-180.00  117
 10  \w      6.00  75.00   1.00    2.11    --   54.00 -57.00-120.00   69
 11  \w    105.00 131.00   1.00    2.11    --  108.00 178.00  30.00   26
 12  \w     54.00  98.00   1.00    2.11    --  108.00 -91.00  30.00   44
 13  \w     97.00 178.00   1.00    2.11    --  108.00  50.00 120.00   81
 14  \w    105.00 131.00   1.00    2.11    --  108.00 111.00   0.00   26
 15  \w     41.00  85.00   1.00    2.11    --  108.00 -63.00 -60.00   44
 16  \w     92.00 129.00   1.00    2.11    --  108.00 -67.00 149.37   37
 17  \w     41.00  67.00   1.00    2.11    --  108.00 -32.00-135.23   26
 18  \w    110.00 136.00   1.00    2.11    --  108.00 -25.00 -30.00   26
 19  \w    153.00 178.00   1.00    2.11    --  108.00  12.00   0.00   25
 20  \w    110.00 136.00   1.00    2.11    --  108.00  12.00   0.00   26
 21  \w     58.00  96.00   1.00    2.11    --  108.00 178.00 -60.00   38
 22  \w     59.00  84.00   1.00    2.11    --  108.00 -16.00 -90.31   25
 23  \w    150.00 178.00   1.00    2.11    --  108.00 111.00 -90.00   28
 24  \w     51.00 113.00   1.00    2.11    --  108.00-111.00-120.00   62
 25  \w     39.00 129.00   1.00    2.11    --  108.00 -50.00  30.00   90
 26  \w     39.00 131.00   1.00    2.11    --  108.00 -77.00   0.00   92
 27  \w     70.00  96.00   1.00    2.11    --  108.00 -25.00 -30.00   26
 28  \w     74.00 112.00   1.00    2.11    --  108.00-111.00  30.00   38
 29  \w     48.00  74.00   1.00    2.11    --  108.00 -67.00 149.37   26
 30  \w     80.00 146.00   1.00    2.11    --  108.00 -91.00-180.00   66
 31  \w     44.00  98.00   1.00    2.11    --  108.00  12.00   0.00   54
 32  \w     92.00 118.00   1.00    2.11    --  108.00 -91.00  60.00   26
 33  \w    120.00 145.00   1.00    2.11    --  108.00  50.00 150.00   25
 34  \w    101.00 126.00   1.00    2.11    --  108.00 -77.00  30.00   25
 35  \w     52.00  78.00   1.00    2.11    --  108.00 -77.00  30.00   26
 36  \w    107.00 132.00   1.00    2.11    --  108.00 178.00 -30.00   25
 37  \w     83.00 156.00   1.00    2.11    --  108.00  38.00-180.00   73
 38  \w     75.00 101.00   1.00    2.11    --  108.00 -91.00 -90.00   26
 39  \w    106.00 133.00   1.00    2.11    --  108.00 -38.00-180.00   27
 40  \w     66.00  91.00   1.00    2.11    --  108.00 -63.00  30.00   25
 41  \w     89.00 125.00   1.00    2.11    --  108.00  50.00  30.00   36
 42  \w     64.00 110.00   1.00    2.11    --  108.00 -50.00-180.00   46
 43  \w     37.00  85.00   1.00    2.11    --  108.00 -38.00-180.00   48
 44  \w     79.00 121.00   1.00    2.11    --  108.00  77.00  30.00   42
 45  \w    114.00 176.00   1.00    2.11    --  108.00  25.00-120.00   62
 46  \w    139.00 164.00   1.00    2.11    --  108.00 111.00-150.00   25
 47  \w     78.00 103.00   1.00    2.11    --  108.00 -32.00-135.23   25
 48  \w     90.00 117.00   1.00    2.11    --  108.00  63.00   0.00   27
 49  \w     89.00 114.00   1.00    2.11    --  108.00  50.00-150.00   25
 50  \w     91.00 116.00   1.00    2.11    --  108.00 -50.00-120.00   25
 51  \w     86.00 111.00   1.00    2.11    --  108.00 178.00 -90.00   25
 52  \w    115.00 140.00   1.00    2.11    --  108.00  38.00 150.00   25
 53  \w     86.00 122.00   1.00    2.11    --  108.00-131.00  26.61   36
 54  \w     82.00 121.00   1.00    2.11    --  108.00-129.00-134.80   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1260060000
_diffrn_orient_matrix_UB_12      -0.0179403000
_diffrn_orient_matrix_UB_13      -0.0125382000
_diffrn_orient_matrix_UB_21      -0.0796751000
_diffrn_orient_matrix_UB_22      -0.1343689000
_diffrn_orient_matrix_UB_23      -0.0323540000
_diffrn_orient_matrix_UB_31      -0.0329895000
_diffrn_orient_matrix_UB_32      0.0238510000
_diffrn_orient_matrix_UB_33      -0.0923858000
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20356
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.700
_diffrn_reflns_theta_min         2.831
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0030(4)
_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   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         7545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0708P)^2^+1.1311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6281
_reflns_number_total             7545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01530d2.cif
_cod_data_source_block           20230217-lty-1406
_cod_depositor_comments          'Adding full bibliography for 7160190.cif.'
_cod_original_cell_volume        1972.36(12)
_cod_database_code               7160190
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C54 H42 O2'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00M(H00M), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00V(H00V), C00W(H00W), C00X(H00X), C010(H010), C013(H013),
 C014(H014), C015(H015), C016(H016), C017(H017), C018(H018), C01B(H01G),
 C01C(H01H), C01D(H01I), C01F(H01M), C01H(H01Q), C01I(H01R), C01J(H01S)
2.b Idealised Me refined as rotating group:
 C00Z(H00A,H00B,H00C), C012(H01A,H01B,H01C), C019(H01D,H01E,H01F), C01E(H01J,
 H01K,H01L), C01G(H01N,H01O,H01P), C01K(H01T,H01U,H01V)
;
_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 1.643
_oxdiff_exptl_absorpt_empirical_full_min 0.538