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_1575711
_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         'C15 H14 O5'
_chemical_formula_sum            'C15 H14 O5'
_chemical_formula_weight         274.26
_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             2022-03-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-06-23 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.416(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3362(3)
_cell_length_b                   8.1868(2)
_cell_length_c                   17.6318(4)
_cell_measurement_reflns_used    4541
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.4470
_cell_measurement_theta_min      4.7690
_cell_volume                     1325.45(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.997
_diffrn_measured_fraction_theta_max 0.961
_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     38.00 103.00   0.50    0.05    --   56.41  15.00 120.00  130
  2  \w     51.00 107.00   0.50    0.05    --   76.49  15.00  30.00  112
  3  \w     90.00 115.00   0.50    0.05    --   76.49  15.00 -60.00   50
  4  \w     57.00  83.00   0.50    0.05    --   76.49  15.00 -60.00   52
  5  \w     55.00  98.00   0.50    0.05    --   56.41  15.00-180.00   86
  6  \w   -106.00 -79.00   0.50    0.05    --  -72.15 -15.00 -60.00   54
  7  \w    -75.00 -44.00   0.50    0.05    --  -72.15 -15.00 -60.00   62
  8  \w   -113.00 -64.00   0.50    0.05    --  -75.36 -15.00   0.00   98
  9  \w    -94.00 -51.00   0.50    0.05    --  -75.36 -15.00  30.00   86
 10  \w   -110.00 -48.00   0.50    0.05    --  -75.36 -15.00  90.00  124
 11  \w    -90.00 -62.00   0.50    0.05    --  -75.36 111.00 -30.00   56
 12  \w    -57.00 -31.00   0.50    0.05    --  -75.36 111.00-150.00   52
 13  \w    -76.00 -31.00   0.50    0.05    --  -75.36 111.00-180.00   90
 14  \w    -96.00 -29.00   0.50    0.05    --  -72.15 125.00-150.00  134
 15  \w    -56.00 -31.00   0.50    0.05    --  -75.36 111.00 -30.00   50
 16  \w    -52.00 -27.00   0.50    0.05    --  -72.15 125.00 150.00   50
 17  \w     44.00  70.00   0.50    0.05    --   76.49-111.00  60.00   52
 18  \w     42.00  88.00   0.50    0.05    --   76.49-111.00  90.00   92
 19  \w     43.00  69.00   0.50    0.05    --   56.41-125.00   0.00   52
 20  \w     36.00  79.00   0.50    0.05    --   76.49-111.00-150.00   86
;
_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      0.1035118000
_diffrn_orient_matrix_UB_12      0.0929317000
_diffrn_orient_matrix_UB_13      0.0634779000
_diffrn_orient_matrix_UB_21      -0.1296373000
_diffrn_orient_matrix_UB_22      0.0431944000
_diffrn_orient_matrix_UB_23      0.0393256000
_diffrn_orient_matrix_UB_31      0.0255765000
_diffrn_orient_matrix_UB_32      -0.1576896000
_diffrn_orient_matrix_UB_33      0.0481633000
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8033
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.204
_diffrn_reflns_theta_min         4.816
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.33a (Rigaku Oxford Diffraction, 2021)
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    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0019(3)
_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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0486P)^2^+0.3381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2163
_reflns_number_total             2464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00925a2.cif
_cod_data_source_block           220167lt_auto
_cod_depositor_comments
'Adding full bibliography for 1575710--1575714.cif.'
_cod_original_cell_volume        1325.46(6)
_cod_database_code               1575711
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.832
_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:
 C3(H3), C5(H5), C6(H6), C15(H15), C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
2.c Idealised tetrahedral OH refined as rotating group:
 O19(H19), O20(H20)
;
_shelx_res_checksum              13962
_shelx_hkl_checksum              96600
_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 2.243
_oxdiff_exptl_absorpt_empirical_full_min 0.577