Synthesis of hydroxyl functionalized aryl/alkyl ketones via visible-light-driven cross-coupling of benzoquinones and alcohols at room temperature
Katkar, Ashwini Vishwasrao; Charpe, Vaibhav Pramod; Hwang, Kuo Chu; Catalysis Science & Technology 15 (2025) 5980–5985; doi:10.1039/D5CY00925A

data_1575713
_publ_section_title
;
 Synthesis of hydroxyl functionalized aryl/alkyl ketones via
 visible-light-driven cross-coupling of benzoquinones and alcohols at room
 temperature
;
_journal_issue                   20
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              5980
_journal_page_last               5985
_journal_paper_doi               10.1039/D5CY00925A
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C8 H7 O'
_chemical_formula_sum            'C8 H7 O'
_chemical_formula_weight         119.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-23
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-07-27 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8443(4)
_cell_length_b                   10.8782(3)
_cell_length_c                   8.8986(3)
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      71.7320
_cell_measurement_theta_min      5.3010
_cell_volume                     1243.34(7)
_computing_cell_refinement       'CrysAlisPro 1.171.44.113a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 44.113a 64-bit (release 02-06-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.113a (Rigaku OD, 2025)'
_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      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -53.00 -13.00   0.50    0.05    --  -57.24 125.00 150.00   80
  2  \w    -89.00 -32.00   0.50    0.05    --  -77.74 111.00 120.00  114
  3  \w    -90.00 -27.00   0.50    0.05    --  -77.74 111.00   0.00  126
  4  \w    -56.00 -31.00   0.50    0.05    --  -77.74 111.00  30.00   50
  5  \w    -89.00 -28.00   0.50    0.05    --  -77.74 111.00-180.00  122
  6  \w    -90.00 -27.00   0.50    0.05    --  -77.74 111.00-120.00  126
  7  \w    -63.00 -33.00   0.50    0.05    --  -77.74 111.00 -60.00   60
  8  \w   -125.00 -86.00   0.50    0.05    --  -77.74 -30.00  90.00   78
  9  \w    -99.00 -71.00   0.50    0.05    --  -57.24 -30.00  30.00   56
 10  \w   -115.00 -78.00   0.50    0.05    --  -68.39 -30.00 -30.00   74
 11  \w   -131.00 -93.00   0.50    0.05    --  -77.74 -30.00  30.00   76
 12  \w   -120.00 -86.00   0.50    0.05    --  -77.74 -30.00 150.00   68
 13  \w   -105.00 -73.00   0.50    0.05    --  -57.24 -30.00 120.00   64
 14  \w     39.00  64.00   0.50    0.05    --   83.09 -95.00 120.00   50
 15  \w     47.00  92.00   0.50    0.05    --   83.09 -95.00 150.00   90
 16  \w     23.00  59.00   0.50    0.05    --   67.76 -95.00  90.00   72
 17  \w     52.00  92.00   0.50    0.05    --   83.09 -95.00  90.00   80
 18  \w     43.00  90.00   0.50    0.05    --   83.09 -95.00 -30.00   94
 19  \w     42.00  92.00   0.50    0.05    --   83.09 -95.00 -90.00  100
 20  \w     40.00  92.00   0.50    0.05    --   83.09 -95.00-150.00  104
 21  \w     11.00  47.00   0.50    0.05    --   55.87 -95.00 -30.00   72
 22  \w     40.00  91.00   0.50    0.05    --   83.09 -95.00  30.00  102
 23  \w     63.00  89.00   0.50    0.05    --   83.09 -95.00  60.00   52
 24  \w    105.00 131.00   0.50    0.05    --   83.09  30.00   0.00   52
 25  \w    100.00 136.00   0.50    0.05    --   83.09  30.00 -90.00   72
 26  \w     77.00 121.00   0.50    0.05    --   67.76  30.00 -90.00   88
 27  \w     93.00 130.00   0.50    0.05    --   83.09  30.00-120.00   74
 28  \w     90.00 115.00   0.50    0.05    --   83.09  30.00-180.00   50
 29  \w     92.00 133.00   0.50    0.05    --   83.09  30.00 -30.00   82
 30  \w     99.00 127.00   0.50    0.05    --   83.09  30.00  30.00   56
 31  \w     91.00 128.00   0.50    0.05    --   83.09  30.00 120.00   74
 32  \w     75.00 113.00   0.50    0.05    --   67.76  30.00 150.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1140639000
_diffrn_orient_matrix_UB_12      -0.0297580000
_diffrn_orient_matrix_UB_13      -0.0390700000
_diffrn_orient_matrix_UB_21      0.0369518000
_diffrn_orient_matrix_UB_22      -0.0946707000
_diffrn_orient_matrix_UB_23      -0.1172212000
_diffrn_orient_matrix_UB_31      -0.0009349000
_diffrn_orient_matrix_UB_32      -0.1011493000
_diffrn_orient_matrix_UB_33      0.1211978000
_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  0.0263
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5833
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.029
_diffrn_reflns_theta_max         67.029
_diffrn_reflns_theta_min         5.329
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.113a (Rigaku Oxford Diffraction, 2025)
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    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1066
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0507P)^2^+0.0792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                1022
_reflns_number_total             1066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00925a2.cif
_cod_data_source_block           2507051lt
_cod_depositor_comments
'Adding full bibliography for 1575710--1575714.cif.'
_cod_database_code               1575713
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C8 H7 O1 '
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.931
_diffrn_oxdiff_digest_hkl
;
43a0c9fa31662ea4a4d4513ab587b836f54c62
;
_diffrn_oxdiff_digest_od_ed
;

;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(4)
 0.0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Fixed Sof: H7A(0.5) H7B(0.5) H7C(0.5) H12B(0.5) H12C(0.5)
4.a Me refined with riding coordinates:
 C12(H12A,H12B,H12C)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              50353
_shelx_hkl_checksum              92651
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.880