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_1575712
_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         'C13 H9 F O3'
_chemical_formula_sum            'C13 H9 F O3'
_chemical_formula_weight         232.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.46230(7)
_cell_length_b                   11.6506(2)
_cell_length_c                   19.6409(3)
_cell_measurement_reflns_used    2955
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.4830
_cell_measurement_theta_min      4.4020
_cell_volume                     1021.10(3)
_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      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 1.000
_diffrn_measured_fraction_theta_max 0.978
_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     63.00  95.00   0.50    0.05    --   56.07  30.00   0.00   64
  2  \w     94.00 120.00   0.50    0.05    --   83.09  30.00 -30.00   52
  3  \w     63.00 107.00   0.50    0.05    --   56.07  30.00 -60.00   88
  4  \w     92.00 126.00   0.50    0.05    --   83.09  30.00   0.00   68
  5  \w     91.00 117.00   0.50    0.05    --   83.09  30.00  30.00   52
  6  \w    102.00 127.00   0.50    0.05    --   83.09  30.00  90.00   50
  7  \w     75.00 101.00   0.50    0.05    --   68.06  30.00 -90.00   52
  8  \w     89.00 126.00   0.50    0.05    --   83.09  30.00-150.00   74
  9  \w     48.00  80.00   0.50    0.05    --   83.09 -95.00-180.00   64
 10  \w     53.00  79.00   0.50    0.05    --   83.09-112.00-117.00   52
 11  \w     45.00  70.00   0.50    0.05    --   56.07-112.00-117.00   50
 12  \w     19.00  44.00   0.50    0.05    --   68.06-112.00-117.00   50
 13  \w   -115.00 -86.00   0.50    0.05    --  -68.83 -30.00-150.00   58
 14  \w   -131.00 -87.00   0.50    0.05    --  -77.74 -30.00-120.00   88
 15  \w   -118.00 -93.00   0.50    0.05    --  -77.74 -30.00 -30.00   50
 16  \w   -128.00 -85.00   0.50    0.05    --  -77.74 -30.00  90.00   86
 17  \w    -68.00 -43.00   0.50    0.05    --  -57.55 112.00 -25.00   50
 18  \w    -50.00 -19.00   0.50    0.05    --  -68.83 112.00 -25.00   62
 19  \w    -60.00 -34.00   0.50    0.05    --  -77.74 112.00 -25.00   52
 20  \w    -92.00 -66.00   0.50    0.05    --  -68.83 112.00 -25.00   52
 21  \w     62.00  87.00   0.50    0.05    --   56.07  30.00 150.00   50
 22  \w     71.00  97.00   0.50    0.05    --   56.07  30.00 -90.00   52
 23  \w    -92.00 -28.00   0.50    0.05    --  -77.74 111.00  90.00  128
 24  \w    -92.00 -66.00   0.50    0.05    --  -77.74 111.00 150.00   52
 25  \w    -56.00 -30.00   0.50    0.05    --  -77.74 111.00 150.00   52
 26  \w    -62.00 -28.00   0.50    0.05    --  -77.74 111.00 -90.00   68
 27  \w     38.00  73.00   0.50    0.05    --   83.09 -95.00 -90.00   70
 28  \w     58.00  91.00   0.50    0.05    --   83.09-111.00 -30.00   66
 29  \w     94.00 132.00   0.50    0.05    --   83.09  30.00  60.00   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      0.1767206000
_diffrn_orient_matrix_UB_12      0.1059582000
_diffrn_orient_matrix_UB_13      0.0242213000
_diffrn_orient_matrix_UB_21      0.1158055000
_diffrn_orient_matrix_UB_22      0.0191290000
_diffrn_orient_matrix_UB_23      -0.0730040000
_diffrn_orient_matrix_UB_31      -0.2730670000
_diffrn_orient_matrix_UB_32      0.0767926000
_diffrn_orient_matrix_UB_33      -0.0152751000
_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  0.0119
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7308
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.727
_diffrn_reflns_theta_min         4.412
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87938
_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    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       0.0064(6)
_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   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0226
_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^)+(0.0320P)^2^+0.1975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0597
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                1945
_reflns_number_total             1977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00925a2.cif
_cod_data_source_block           2506068lt_auto
_cod_depositor_comments
'Adding full bibliography for 1575710--1575714.cif.'
_cod_database_code               1575712
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.816
_diffrn_oxdiff_digest_hkl
;
43d6dc4b06cc10c48e5f0b80a4c93a98c0c2f1
;
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised tetrahedral OH refined as rotating group:
 O9(H9), O10(H10)
;
_shelx_res_checksum              78180
_shelx_hkl_checksum              56114
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.819