Visible-light-induced photoredox-catalyzed dearomative dicarboxylation of arenes using formate and CO2
Li, Jiayuan; Zhang, Zeyu; Yi, Yaping; Xi, Chanjuan; Green Chemistry 27 (2025) 3443–3450; doi:10.1039/D5GC00240K

data_7250052
_publ_section_title
;
 Visible-light-induced photoredox-catalyzed dearomative dicarboxylation of
 arenes using formate and CO2
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              3443
_journal_page_last               3450
_journal_paper_doi               10.1039/D5GC00240K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 O4'
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.31
_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             2024-11-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-27 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                87.703(6)
_cell_angle_beta                 79.960(6)
_cell_angle_gamma                63.498(8)
_cell_formula_units_Z            2
_cell_length_a                   7.4833(6)
_cell_length_b                   8.3504(7)
_cell_length_c                   13.1170(8)
_cell_measurement_reflns_used    6042
_cell_measurement_temperature    169.9(3)
_cell_measurement_theta_max      75.5260
_cell_measurement_theta_min      3.4100
_cell_volume                     721.64(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.9(3)
_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 0.960
_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    -21.00  15.00   0.50    0.05    --  -46.51  19.00-180.00   72
  2  \w    -18.00   8.00   0.50    0.05    --  -46.51  19.00-150.00   52
  3  \w    -18.00  12.00   0.50    0.05    --  -46.51  19.00 -90.00   60
  4  \w     24.00  71.00   0.50    0.05    --   46.51  77.00  90.00   94
  5  \w     73.00 119.00   0.50    0.05    --   46.51  77.00  90.00   92
  6  \w     93.00 147.00   0.50    0.05    --  105.35 103.00  96.00  108
  7  \w     83.00 176.00   0.50    0.05    --  105.35  77.00  60.00  186
  8  \w    118.00 166.00   0.50    0.05    --  105.35  15.00-180.00   96
  9  \w     33.00  66.00   0.50    0.05    --  105.35 -61.00-120.00   66
 10  \w     41.00  70.00   0.50    0.05    --  105.35 -61.00-150.00   58
 11  \w     35.00  75.00   0.50    0.05    --  105.35 -61.00-180.00   80
 12  \w     36.00  73.00   0.50    0.05    --  105.35 -61.00 -30.00   74
 13  \w     35.00  60.00   0.50    0.05    --  105.35 -61.00   0.00   50
 14  \w     33.00 108.00   0.50    0.05    --  105.35 -77.00 120.00  150
 15  \w     34.00  63.00   0.50    0.05    --  105.35 -61.00 150.00   58
 16  \w     78.00 104.00   0.50    0.05    --  105.35 -94.00 150.00   52
 17  \w     35.00 106.00   0.50    0.05    --  105.35-103.00  -5.00  142
 18  \w     36.00  73.00   0.50    0.05    --  105.35-125.00  30.00   74
 19  \w     78.00 111.00   0.50    0.05    --  105.35-125.00  30.00   66
 20  \w     38.00 109.00   0.50    0.05    --  105.35-125.00  90.00  142
 21  \w     60.00 105.00   0.50    0.05    --  105.35 -94.00  90.00   90
 22  \w     60.00  91.00   0.50    0.05    --   46.51-125.00 -30.00   62
 23  \w      0.00  82.00   0.50    0.05    --   46.51-103.00  -5.00  164
 24  \w     22.00  54.00   0.50    0.05    --   46.51-125.00 -30.00   64
 25  \w   -124.00 -89.00   0.50    0.05    -- -104.50 142.00-163.60   70
 26  \w   -111.00 -45.00   0.50    0.05    -- -104.50 125.00 -90.00  132
 27  \w    -82.00   7.00   0.50    0.05    --  -46.51 103.00  96.00  178
 28  \w   -106.00 -33.00   0.50    0.05    -- -104.50 103.00  96.00  146
 29  \w   -124.00 -88.00   0.50    0.05    -- -104.50 -15.00 120.00   72
 30  \w   -174.00-113.00   0.50    0.05    -- -104.50 -52.00  75.62  122
 31  \w   -165.00-139.00   0.50    0.05    -- -104.50 -45.00  90.00   52
 32  \w   -173.00-139.00   0.50    0.05    -- -104.50 -15.00 120.00   68
 33  \w   -135.00 -90.00   0.50    0.05    -- -104.50 -45.00  90.00   90
 34  \w   -160.00-106.00   0.50    0.05    -- -104.50 -45.00  30.00  108
 35  \w    -90.00 -54.00   0.50    0.05    --  -46.51 -38.00 -30.00   72
 36  \w   -174.00 -85.00   0.50    0.05    -- -104.50-103.00  -5.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0850408000
_diffrn_orient_matrix_UB_12      -0.1410122000
_diffrn_orient_matrix_UB_13      0.0805337000
_diffrn_orient_matrix_UB_21      -0.1891124000
_diffrn_orient_matrix_UB_22      0.1093720000
_diffrn_orient_matrix_UB_23      0.0813370000
_diffrn_orient_matrix_UB_31      -0.1076747000
_diffrn_orient_matrix_UB_32      -0.1035831000
_diffrn_orient_matrix_UB_33      -0.0339269000
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8294
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.886
_diffrn_reflns_theta_min         3.425
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0118(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0514P)^2^+0.1999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc00240k2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7250052--7250053.cif.'
_cod_database_code               7250052
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHO
_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 Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C2(H2), C8(H8), C5(H5), C3(H3), C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              39450
_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 1.750
_oxdiff_exptl_absorpt_empirical_full_min 0.540