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_7250053
_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         'C7 H5 O2'
_chemical_formula_sum            'C7 H5 O2'
_chemical_formula_weight         121.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-01-14 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.56956(10)
_cell_length_b                   10.83565(18)
_cell_length_c                   18.2517(3)
_cell_measurement_reflns_used    8410
_cell_measurement_temperature    170.0(4)
_cell_measurement_theta_max      75.1530
_cell_measurement_theta_min      4.8430
_cell_volume                     1101.49(3)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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     22.00  47.00   0.50    0.05    --   42.87  57.00 -60.00   50
  2  \w     73.00  99.00   0.50    0.05    --   42.87  57.00 -60.00   52
  3  \w     21.00 116.00   0.50    0.05    --   42.87  61.00-179.00  190
  4  \w     21.00  81.00   0.50    0.05    --   42.87-125.00 -30.00  120
  5  \w     37.00 111.00   0.50    0.07    --  108.44-125.00-150.00  148
  6  \w     37.00  76.00   0.50    0.07    --  108.44-125.00 -90.00   78
  7  \w     80.00 105.00   0.50    0.07    --  108.44-125.00 -90.00   50
  8  \w     36.00  66.00   0.50    0.07    --  108.44-108.00  22.57   60
  9  \w     70.00 107.00   0.50    0.07    --  108.44-108.00  22.57   74
 10  \w     73.00 110.00   0.50    0.07    --  108.44-125.00  30.00   74
 11  \w     36.00  82.00   0.50    0.07    --  108.44 -94.00 -90.00   92
 12  \w     36.00 104.00   0.50    0.07    --  108.44 -94.00  30.00  136
 13  \w     63.00 104.00   0.50    0.07    --  108.44 -94.00  60.00   82
 14  \w     39.00  80.00   0.50    0.07    --  108.44-125.00 120.00   82
 15  \w     64.00  89.00   0.50    0.07    --  108.44 -77.00 120.00   50
 16  \w     34.00  75.00   0.50    0.07    --  108.44 -61.00  42.00   82
 17  \w    -30.00  65.00   0.50    0.05    --   42.87 -61.00  42.00  190
 18  \w     85.00 178.00   0.50    0.07    --  108.44  30.00 120.00  186
 19  \w     86.00 132.00   0.50    0.07    --  108.44  30.00 -30.00   92
 20  \w    141.00 167.00   0.50    0.07    --  108.44  30.00 -30.00   52
 21  \w     85.00 178.00   0.50    0.07    --  108.44  61.00-179.00  186
 22  \w    127.00 174.00   0.50    0.07    --  108.44 125.00-120.00   94
 23  \w     82.00 170.00   0.50    0.07    --  108.44 125.00   0.00  176
 24  \w     80.00 114.00   0.50    0.07    --  108.44 125.00-120.00   68
 25  \w   -116.00 -19.00   0.50    0.05    --  -42.87 -61.00  42.00  194
 26  \w   -160.00-121.00   0.50    0.07    -- -104.50 -72.00 131.82   78
 27  \w   -174.00 -81.00   0.50    0.07    -- -104.50 -61.00  42.00  186
 28  \w   -127.00 -86.00   0.50    0.07    -- -104.50 -30.00 -90.00   82
 29  \w   -169.00-133.00   0.50    0.07    -- -104.50 -30.00 -90.00   72
 30  \w   -169.00-135.00   0.50    0.07    -- -104.50-125.00-150.00   68
 31  \w    -22.00  37.00   0.50    0.05    --  -42.87  19.00 150.00  118
 32  \w    -59.00 -32.00   0.50    0.07    -- -104.50  61.00  30.00   54
 33  \w   -132.00 -90.00   0.50    0.07    -- -104.50-125.00-150.00   84
 34  \w    -60.00  23.00   0.50    0.05    --  -42.87  61.00-179.00  166
 35  \w    -68.00 -30.00   0.50    0.07    -- -104.50  61.00-179.00   76
 36  \w   -110.00 -51.00   0.50    0.07    -- -104.50 125.00 -90.00  118
 37  \w   -129.00-103.00   0.50    0.07    -- -104.50 150.00 139.79   52
 38  \w    -91.00 -51.00   0.50    0.07    -- -104.50 150.00 139.79   80
 39  \w    -94.00 -68.00   0.50    0.07    -- -104.50 125.00 150.00   52
;
_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      0.2629446000
_diffrn_orient_matrix_UB_12      0.0244607000
_diffrn_orient_matrix_UB_13      -0.0217900000
_diffrn_orient_matrix_UB_21      0.0838861000
_diffrn_orient_matrix_UB_22      -0.0979159000
_diffrn_orient_matrix_UB_23      0.0556192000
_diffrn_orient_matrix_UB_31      -0.0177848000
_diffrn_orient_matrix_UB_32      -0.1001063000
_diffrn_orient_matrix_UB_33      -0.0596662000
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11646
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.681
_diffrn_reflns_theta_min         4.846
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55444
_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    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0028(6)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0458P)^2^+0.4416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1074
_reflns_number_total             1135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc00240k2.cif
_cod_data_source_block           tx17159_auto
_cod_depositor_comments
'Adding full bibliography for 7250052--7250053.cif.'
_cod_database_code               7250053
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              13620
_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 1.633
_oxdiff_exptl_absorpt_empirical_full_min 0.662