H-Bond Directed Photocatalytic Site-Selective α-C-H Functionalization of Alcohols with p-Quinone Methides
Sandha, Sabhya; Tripathi, Chandra Bhushan; Chemical Communications  (2026) –; doi:10.1039/D6CC00863A

data_7135639
_publ_section_title
;
 H-bond-directed photocatalytic site-selective &#x3b1;-C-H
 functionalization of alcohols with <i>p</i>-quinone methides.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7417
_journal_page_last               7420
_journal_paper_doi               10.1039/d6cc00863a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C24 H35 O5 P'
_chemical_formula_sum            'C24 H35 O5 P'
_chemical_formula_weight         434.516
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-08-06
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-11 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.6663(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.61485(13)
_cell_length_b                   16.6523(2)
_cell_length_c                   16.0640(2)
_cell_measurement_reflns_used    11316
_cell_measurement_temperature    296.06(10)
_cell_measurement_theta_max      77.2930
_cell_measurement_theta_min      3.8240
_cell_volume                     2563.47(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.06(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9497
_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    -47.00 -19.00   0.50    0.24    --  -91.75  47.00-136.00   56
  2  \w    -54.00 -27.00   0.50    0.24    --  -91.75  57.00 -60.00   54
  3  \w    -50.00 -24.00   0.50    0.24    --  -91.75  57.00   0.00   52
  4  \w    -50.00 -23.00   0.50    0.24    --  -91.75  57.00  60.00   54
  5  \w    -80.00 -54.00   0.50    0.24    --  -91.75 125.00  60.00   52
  6  \w    -72.00 -47.00   0.50    0.06    --  -47.26 -38.00   0.00   50
  7  \w   -153.00 -91.00   0.50    0.24    --  -91.75 -99.00-180.00  124
  8  \w   -117.00 -85.00   0.50    0.06    --  -47.26 -38.00   0.00   64
  9  \w   -121.00 -89.00   0.50    0.24    --  -91.75 -47.00  74.00   64
 10  \w   -118.00 -35.00   0.50    0.06    --  -47.26 -47.00  74.00  166
 11  \w     15.00  51.00   0.50    0.06    --   47.26 -47.00  74.00   72
 12  \w     37.00  65.00   0.50    0.24    --  109.68 -57.00 150.00   56
 13  \w     37.00 103.00   0.50    0.24    --  109.68 -77.00  90.00  132
 14  \w     39.00  68.00   0.50    0.24    --  109.68 -57.00 -30.00   58
 15  \w     39.00  64.00   0.50    0.24    --  109.68 -57.00 -60.00   50
 16  \w     42.00  68.00   0.50    0.24    --  109.68 -57.00 -90.00   52
 17  \w     37.00 103.00   0.50    0.24    --  109.68 -77.00-120.00  132
 18  \w     38.00  66.00   0.50    0.24    --  109.68 -57.00-180.00   56
 19  \w     45.00 106.00   0.50    0.24    --  109.68 -99.00-180.00  122
 20  \w     54.00 102.00   0.50    0.24    --  109.68 -99.00  60.00   96
 21  \w    -11.00  28.00   0.50    0.06    --  -47.26  19.00   0.00   78
 22  \w    -51.00  24.00   0.50    0.06    --  -47.26  47.00-136.00  150
 23  \w     52.00  77.00   0.50    0.06    --   47.26  47.00-136.00   50
 24  \w    108.00 178.00   0.50    0.24    --  109.68  47.00-136.00  140
 25  \w    153.00 178.00   0.50    0.24    --  109.68  19.00-180.00   50
 26  \w    106.00 132.00   0.50    0.24    --  109.68  19.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0830355000
_diffrn_orient_matrix_UB_12      -0.0464207000
_diffrn_orient_matrix_UB_13      0.0624998000
_diffrn_orient_matrix_UB_21      -0.1376801000
_diffrn_orient_matrix_UB_22      0.0263783000
_diffrn_orient_matrix_UB_23      -0.0480123000
_diffrn_orient_matrix_UB_31      0.0029573000
_diffrn_orient_matrix_UB_32      -0.0755304000
_diffrn_orient_matrix_UB_33      -0.0551782000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9497
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18209
_diffrn_reflns_point_group_measured_fraction_full 0.9961
_diffrn_reflns_point_group_measured_fraction_max 0.9497
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.94
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_description       block
_exptl_crystal_F_000             940.131
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.2993
_refine_diff_density_min         -0.5425
_refine_diff_density_rms         0.0757
_refine_ls_d_res_high            0.7883
_refine_ls_d_res_low             11.5415
_refine_ls_goodness_of_fit_ref   1.0456
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0456
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          -0.0155
_refine_ls_shift/su_mean         0.0012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+1.1518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -12
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -9
_reflns_number_gt                4412
_reflns_number_total             5210
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d6cc00863a2.cif
_cod_data_source_block           XRF24062025B_auto
_cod_depositor_comments          'Adding full bibliography for 7135639.cif.'
_cod_original_cell_volume        2563.49(6)
_cod_database_code               7135639
_chemical_oxdiff_formula         'C24 H35 O5  P'
_cell_oxdiff_angle_alpha         89.9992(10)
_cell_oxdiff_angle_beta          94.6620(11)
_cell_oxdiff_angle_gamma         89.9980(11)
_cell_oxdiff_length_a            9.61189(15)
_cell_oxdiff_length_b            16.6554(2)
_cell_oxdiff_length_c            16.0659(2)
_cell_oxdiff_measurement_reflns_used 11316
_cell_oxdiff_volume              2563.48(6)
_diffrn_oxdiff_digest_hkl
;
01940478832ac202b9495da292b4c3849c0c01
;
_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 Ternary CH refined with riding coordinates:
 C3(H3a), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C17(H17), C1d(H1d), C1e(H1e), C1f(H1f), C1g(H1g)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C18(H18a,H18b,
 H18c), C19(H19a,H19b,H19c), C1a(H1aa,H1ab,H1ac), C1b(H1ba,H1bb,H1bc), C1c(H1ca,
 H1cb,H1cc)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.721