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_1575714
_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         'C14 H12 O3'
_chemical_formula_sum            'C14 H12 O3'
_chemical_formula_weight         228.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-14
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-07-18 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.187(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.82007(19)
_cell_length_b                   23.6447(6)
_cell_length_c                   12.4839(3)
_cell_measurement_reflns_used    4207
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      72.3970
_cell_measurement_theta_min      4.1580
_cell_volume                     2205.24(10)
_computing_cell_refinement       'CrysAlisPro 1.171.44.113a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.113a (Rigaku OD, 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      99.98(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 0.966
_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     89.00 129.00   0.50    0.05    --   83.09  30.00-180.00   80
  2  \w     63.00  89.00   0.50    0.05    --   56.07  30.00-180.00   52
  3  \w     75.00 122.00   0.50    0.05    --   68.06  30.00-150.00   94
  4  \w     45.00  71.00   0.50    0.05    --   83.09  15.00 -60.00   52
  5  \w    101.00 132.00   0.50    0.05    --   83.09  15.00 -60.00   62
  6  \w     91.00 131.00   0.50    0.05    --   83.09  30.00  90.00   80
  7  \w     14.00  53.00   0.50    0.05    --   56.07-103.00  67.00   78
  8  \w     28.00  53.00   0.50    0.05    --   68.06-103.00  67.00   50
  9  \w     39.00  64.00   0.50    0.05    --   83.09-103.00  67.00   50
 10  \w     38.00  75.00   0.50    0.05    --   83.09 -95.00-120.00   74
 11  \w     41.00  89.00   0.50    0.05    --   83.09 -95.00  90.00   96
 12  \w     64.00  89.00   0.50    0.05    --   83.09 -95.00 120.00   50
 13  \w     47.00  88.00   0.50    0.05    --   83.09 -95.00 150.00   82
 14  \w     19.00  65.00   0.50    0.05    --   56.07 -95.00 120.00   92
 15  \w   -111.00 -65.00   0.50    0.05    --  -57.55 -30.00 -30.00   92
 16  \w   -131.00 -84.00   0.50    0.05    --  -77.74 -30.00 -60.00   94
 17  \w   -130.00 -99.00   0.50    0.05    --  -77.74 -30.00-150.00   62
 18  \w   -128.00 -85.00   0.50    0.05    --  -77.74 -30.00  60.00   86
 19  \w   -121.00 -75.00   0.50    0.05    --  -68.83 -30.00 120.00   92
 20  \w    -77.00 -52.00   0.50    0.05    --  -68.83 103.00 169.00   50
 21  \w    -88.00 -37.00   0.50    0.05    --  -77.74 103.00 169.00  102
 22  \w    -46.00 -20.00   0.50    0.05    --  -57.55 103.00 169.00   52
 23  \w    -80.00 -27.00   0.50    0.05    --  -77.74 111.00   0.00  106
 24  \w    -92.00 -38.00   0.50    0.05    --  -77.74 111.00 -90.00  108
;
_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      0.0101909000
_diffrn_orient_matrix_UB_12      -0.0299190000
_diffrn_orient_matrix_UB_13      -0.1076313000
_diffrn_orient_matrix_UB_21      0.0706596000
_diffrn_orient_matrix_UB_22      0.0548599000
_diffrn_orient_matrix_UB_23      -0.0382627000
_diffrn_orient_matrix_UB_31      0.1933745000
_diffrn_orient_matrix_UB_32      -0.0185239000
_diffrn_orient_matrix_UB_33      0.0602895000
_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  0.0235
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15543
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.873
_diffrn_reflns_theta_min         3.739
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96768
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00080(13)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.6328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3615
_reflns_number_total             4257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00925a2.cif
_cod_data_source_block           2506069lt_auto
_cod_depositor_comments
'Adding full bibliography for 1575710--1575714.cif.'
_cod_original_cell_volume        2205.23(10)
_cod_database_code               1575714
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.897
_diffrn_oxdiff_digest_hkl
;
4361fec65a1fa4dcbd6c063b4ae1c101fd1daf
;
_diffrn_oxdiff_digest_od_ed
;

;
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16), C19(H19),
 C21(H21), C22(H22), C29(H29), C30(H30), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
2.c Idealised tetrahedral OH refined as rotating group:
 O9(H9), O10(H10), O26(H26), O27(H27)
;
_shelx_res_checksum              85859
_shelx_hkl_checksum              785
_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 1.158
_oxdiff_exptl_absorpt_empirical_full_min 0.901