Visible-light-induced synthesis of bibenzofuranones <i>via</i> a cerium-mediated energy transfer process.
Lv, Jiaoyue; Lang, Yatao; Li, Chao-Jun; Zeng, Huiying; Chemical communications (Cambridge, England) 61 (2025) 4054–4057; doi:10.1039/d4cc06761d

data_7134265
_publ_section_title
;
 Visible-light-induced synthesis of bibenzofuranones <i>via</i> a
 cerium-mediated energy transfer process.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4054
_journal_page_last               4057
_journal_paper_doi               10.1039/d4cc06761d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C36 H32 Cl2 O4'
_chemical_formula_sum            'C36 H32 Cl2 O4'
_chemical_formula_weight         599.51
_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             2025-01-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-16 deposited with the CCDC.	2025-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                79.3380(10)
_cell_angle_beta                 64.387(2)
_cell_angle_gamma                79.3720(10)
_cell_formula_units_Z            2
_cell_length_a                   12.1015(2)
_cell_length_b                   12.1074(2)
_cell_length_c                   12.1083(2)
_cell_measurement_reflns_used    19197
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      75.0430
_cell_measurement_theta_min      4.0800
_cell_volume                     1561.17(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      air
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.935
_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    -55.00  13.00   0.50    0.50    --  -43.05  96.00-125.00  136
  2  \w      5.00  36.00   0.50    0.50    --   40.00  90.00   4.81   62
  3  \w     25.00  53.00   0.50    0.50    --   43.05  57.00   0.00   56
  4  \w     71.00 110.00   0.50    0.50    --   43.05  57.00   0.00   78
  5  \w     72.00  98.00   0.50    0.50    --   60.00  79.00 -61.19   52
  6  \w     75.00 118.00   0.50    0.50    --   43.05  37.00 -90.00   86
  7  \w    113.00 139.00   0.50    0.50    --   68.00  79.00-101.89   52
  8  \w     99.00 131.00   0.50    0.50    --   60.00  81.00-170.76   64
  9  \w     88.00 142.00   0.50    2.00    --  109.26  96.00-125.00  108
 10  \w     64.00  97.00   0.50    2.00    --   88.00  64.00-140.02   66
 11  \w     32.00  63.00   0.50    0.50    --   60.00  79.00 -61.19   62
 12  \w     34.00  59.00   0.50    0.50    --   64.00  80.00 -45.82   50
 13  \w     38.00  66.00   0.50    0.50    --   68.00  79.00-101.89   56
 14  \w     38.00  65.00   0.50    0.50    --   68.00  80.00-130.44   54
 15  \w     21.00  47.00   0.50    0.50    --   43.05  57.00 -90.00   52
 16  \w     22.00  52.00   0.50    0.50    --   43.05  37.00 -90.00   60
 17  \w      9.00  34.00   0.50    0.50    --   44.00  90.00 -65.03   50
 18  \w      9.00  35.00   0.50    0.50    --   44.00  91.00-118.22   52
 19  \w     30.00  56.00   0.50    0.50    --   60.00  81.00-170.76   52
 20  \w     37.00  63.00   0.50    0.50    --   68.00  81.00 -19.59   52
 21  \w     38.00  64.00   0.50    0.50    --   68.00  80.00  32.88   52
 22  \w     36.00  62.00   0.50    0.50    --   64.00  76.00  77.91   52
 23  \w     53.00 116.00   0.50    0.50    --   43.05  77.00 120.00  126
 24  \w     38.00  64.00   0.50    0.50    --   68.00  80.00  91.72   52
 25  \w     41.00  76.00   0.50    0.50    --   72.00  81.00 121.18   70
 26  \w     21.00  63.00   0.50    0.50    --   43.05  37.00 120.00   84
 27  \w     31.00  83.00   0.50    0.50    --   60.00  81.00 137.40  104
 28  \w     31.00  57.00   0.50    0.50    --   60.00  80.00  45.29   52
 29  \w     14.00  39.00   0.50    0.50    --   43.05  77.00 120.00   50
 30  \w      9.00  34.00   0.50    0.50    --   44.00  91.00 138.38   50
 31  \w    -71.00 -44.00   0.50    2.00    --  -72.00 -76.00  15.52   54
 32  \w    -41.00 -16.00   0.50    0.50    --  -48.00 -87.00   8.67   50
 33  \w    -41.00 -16.00   0.50    0.50    --  -48.00 -87.00  94.47   50
 34  \w    -73.00 -46.00   0.50    2.00    --  -76.00 -81.00  -2.14   54
 35  \w    -74.00 -49.00   0.50    2.00    --  -76.00 -71.00  44.25   50
 36  \w    -80.00 -54.00   0.50    2.00    --  -80.00 -69.00 105.80   52
 37  \w    -76.00 -49.00   0.50    2.00    --  -76.00 -75.00 146.34   54
 38  \w    -77.00 -48.00   0.50    2.00    --  -76.00 -75.00 168.45   58
 39  \w    -82.00 -52.00   0.50    2.00    --  -80.00 -75.00  91.04   60
 40  \w    -83.00 -57.00   0.50    2.00    --  -84.00 -74.00 134.64   52
 41  \w    -88.00 -63.00   0.50    2.00    --  -92.00 -76.00 124.12   50
 42  \w    -92.00 -60.00   0.50    2.00    --  -88.00 -75.00  76.90   64
 43  \w    -85.00 -59.00   0.50    2.00    --  -88.00 -77.00  34.26   52
 44  \w    -90.00 -50.00   0.50    2.00    --  -76.00 -69.00   5.64   80
 45  \w    -80.00 -54.00   0.50    2.00    --  -80.00 -70.00 -61.30   52
 46  \w    -78.00 -52.00   0.50    2.00    --  -80.00 -75.00 -91.48   52
 47  \w    -81.00 -55.00   0.50    2.00    --  -80.00 -69.00-141.38   52
 48  \w    -72.00 -46.00   0.50    2.00    --  -76.00 -78.00-164.33   52
 49  \w    -39.00 -14.00   0.50    0.50    --  -48.00 -89.00-168.80   50
 50  \w    -81.00 -56.00   0.50    2.00    --  -80.00 -68.00 -47.69   50
 51  \w    -84.00 -59.00   0.50    2.00    --  -88.00 -76.00 -18.85   50
 52  \w    -88.00 -63.00   0.50    2.00    --  -92.00 -76.00 -90.54   50
 53  \w    -83.00 -58.00   0.50    2.00    --  -84.00 -75.00-139.78   50
 54  \w    -92.00 -57.00   0.50    2.00    --  -84.00 -73.00-111.26   70
 55  \w    -96.00 -64.00   0.50    2.00    --  -92.00 -74.00-134.32   64
 56  \w   -103.00 -71.00   0.50    2.00    -- -100.00 -77.00 -57.39   64
 57  \w   -110.00 -60.00   0.50    2.00    --  -88.00 -74.00-164.04  100
 58  \w   -123.00 -87.00   0.50    2.00    -- -100.00 -77.00-180.00   72
 59  \w   -142.00-107.00   0.50    2.00    --  -92.00 -74.00-134.32   70
 60  \w   -142.00-110.00   0.50    2.00    --  -92.00 -76.00 -90.54   64
 61  \w   -139.00 -72.00   0.50    2.00    -- -100.00 -77.00 -30.00  134
 62  \w   -100.00 -68.00   0.50    2.00    --  -96.00 -75.00  58.23   64
 63  \w   -104.00 -66.00   0.50    2.00    --  -96.00 -80.00 118.29   76
 64  \w   -105.00 -72.00   0.50    2.00    -- -100.00 -77.00 107.09   66
 65  \w   -121.00 -65.00   0.50    2.00    --  -92.00 -73.00 172.95  112
 66  \w   -129.00 -67.00   0.50    2.00    --  -92.00 -68.00 145.08  124
 67  \w   -136.00 -98.00   0.50    2.00    -- -100.00 -96.00 125.00   76
 68  \w   -142.00-116.00   0.50    2.00    --  -88.00 -75.00  76.90   52
 69  \w   -131.00 -72.00   0.50    2.00    -- -100.00 -77.00  30.00  118
 70  \w   -120.00 -72.00   0.50    2.00    -- -100.00 -81.00  -1.11   96
 71  \w   -153.00-121.00   0.50    2.00    -- -100.00 -77.00 -57.39   64
 72  \w   -170.00 -67.00   0.50    2.00    --  -96.00 -76.00   9.40  206
 73  \w   -149.00-123.00   0.50    2.00    --  -92.00 -73.00 172.95   52
 74  \w   -156.00-123.00   0.50    2.00    --  -84.00 -74.00 134.64   66
 75  \w   -163.00-108.00   0.50    2.00    -- -100.00 -77.00 107.09  110
 76  \w   -150.00 -70.00   0.50    2.00    -- -100.00 -79.00  47.82  160
 77  \w    -54.00 -24.00   0.50    2.00    -- -100.00  45.00  90.00   60
 78  \w    -74.00 -31.00   0.50    2.00    -- -100.00  61.00  30.00   86
 79  \w    -80.00 -32.00   0.50    2.00    -- -100.00 136.00 110.89   96
 80  \w   -112.00 -40.00   0.50    2.00    -- -100.00 125.00   0.00  144
 81  \w    -59.00 -34.00   0.50    2.00    -- -100.00 147.00 -82.18   50
 82  \w    -76.00 -50.00   0.50    2.00    -- -100.00 125.00-180.00   52
 83  \w    -87.00 -26.00   0.50    2.00    -- -100.00  96.00-125.00  122
 84  \w   -114.00 -63.00   0.50    0.50    --  -43.05 179.00-150.00  102
 85  \w   -112.00 -36.00   0.50    2.00    -- -100.00 125.00 -90.00  152
 86  \w   -110.00 -79.00   0.50    2.00    -- -100.00 125.00-180.00   62
 87  \w   -127.00 -80.00   0.50    2.00    -- -100.00 147.00 -82.18   94
 88  \w   -120.00 -94.00   0.50    2.00    -- -100.00 136.00 110.89   52
 89  \w   -108.00 -26.00   0.50    2.00    -- -100.00  77.00 120.00  164
 90  \w    -17.00  76.00   0.50    0.50    --   43.05 -96.00 125.00  186
 91  \w     68.00 102.00   0.50    2.00    --  109.26 -96.00 125.00   68
 92  \w     60.00 110.00   0.50    2.00    --  109.26-125.00 120.00  100
 93  \w     38.00  64.00   0.50    2.00    --  109.26 -96.00 125.00   52
 94  \w     36.00 101.00   0.50    2.00    --  109.26 -94.00 -60.00  130
 95  \w     42.00  94.00   0.50    2.00    --  109.26 -94.00-180.00  104
 96  \w     30.00  71.00   0.50    0.50    --   43.05 -99.00-120.00   82
 97  \w     35.00  68.00   0.50    2.00    --  109.26 -61.00-150.00   66
 98  \w   -168.00 -71.00   0.50    2.00    -- -100.00 -78.00 -99.24  194
 99  \w   -170.00-106.00   0.50    2.00    --  -96.00 -75.00  58.23  128
100  \w   -174.00 -86.00   0.50    2.00    -- -100.00 -76.00 142.27  176
101  \w   -173.00 -72.00   0.50    2.00    -- -100.00 -78.00 -41.33  202
102  \w   -172.00 -72.00   0.50    2.00    -- -100.00 -76.00-138.41  200
103  \w   -170.00-140.00   0.50    2.00    -- -100.00 -77.00-180.00   60
104  \w   -174.00 -71.00   0.50    2.00    -- -100.00 -76.00  82.27  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0125941000
_diffrn_orient_matrix_UB_12      -0.1223895000
_diffrn_orient_matrix_UB_13      -0.0075951000
_diffrn_orient_matrix_UB_21      0.1161527000
_diffrn_orient_matrix_UB_22      -0.0007329000
_diffrn_orient_matrix_UB_23      -0.1224863000
_diffrn_orient_matrix_UB_31      0.0810029000
_diffrn_orient_matrix_UB_32      -0.0449511000
_diffrn_orient_matrix_UB_33      0.0716435000
_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  0.0499
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            42561
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.636
_diffrn_reflns_theta_min         3.741
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0628P)^2^+0.2327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4768
_reflns_number_total             6077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06761d2.cif
_cod_data_source_block           lvjiaoyue_0305
_cod_depositor_comments          'Adding full bibliography for 7134265.cif.'
_cod_database_code               7134265
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00W(H00W), C00Z(H00Z)
2.b Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C), C012(H01D,H01E,H01F), C013(H01G,H01H,H01I), C014(H01J,
 H01K,H01L), C015(H01M,H01N,H01O), C016(H01P,H01Q,H01R)
;
_shelx_res_checksum              75913
_shelx_hkl_checksum              27896
_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 2.475
_oxdiff_exptl_absorpt_empirical_full_min 0.646