Water-soluble imidazolium-functionalized Cu(ii) complex as a recyclable catalyst for allylic and benzylic oxidation.
Huo, X.; Guagliardo, M.; Duke, X.; Bouley, B.; Gorden, A. E. V.; RSC advances 16 (2026) 1335–1343; doi:10.1039/d5ra09017b

data_7251737
_publ_section_title
;
 Water-soluble imidazolium-functionalized Cu(ii) complex as a recyclable
 catalyst for allylic and benzylic oxidation.
;
_journal_issue                   2
_journal_name_full               'RSC advances'
_journal_page_first              1335
_journal_page_last               1343
_journal_paper_doi               10.1039/d5ra09017b
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety
'0.5(C28 H25.33 Cu N8 O2), 0.5(C28 H26 Cu N8 O2), 2(F6 P), 0.5(C2 H3 N)'
_chemical_formula_sum            'C29 H27.17 Cu F12 N8.5 O2 P2'
_chemical_formula_weight         880.24
_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_block_doi                 10.5517/ccdc.csd.cc2p8cfs
_audit_creation_date             2025-07-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2025-08-14 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.683(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.8055(2)
_cell_length_b                   46.2813(10)
_cell_length_c                   18.7210(3)
_cell_measurement_reflns_used    20082
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2280
_cell_measurement_theta_min      2.5490
_cell_volume                     7591.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (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
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     57.00  84.00   0.50   30.00    --   49.41-109.00 116.00   54
  2  \w     22.00  53.00   0.50   30.00    --   49.41-109.00 116.00   62
  3  \w   -112.00 -87.00   0.50  120.00    --  -90.00-109.00 116.00   50
  4  \w    -72.00 -30.00   0.50  120.00    --  -90.00 109.00-147.00   84
  5  \w    105.00 165.00   0.50  120.00    --  111.50 109.00-147.00  120
  6  \w     68.00 107.00   0.50  120.00    --  111.50-109.00 116.00   78
  7  \w    -82.00 -15.00   0.50   30.00    --  -49.41 109.00-147.00  134
  8  \w   -113.00 -75.00   0.50   30.00    --  -49.41-125.00 -30.00   76
  9  \w    -22.00  23.00   0.50   30.00    --  -49.41  19.00 -90.00   90
 10  \w    -15.00  11.00   0.50   30.00    --  -49.41  19.00-120.00   52
 11  \w   -111.00 -74.00   0.50   30.00    --  -49.41-125.00 150.00   74
 12  \w   -110.00 -84.00   0.50   30.00    --  -49.41-125.00 -90.00   52
 13  \w    -23.00  24.00   0.50   30.00    --  -49.41  19.00 150.00   94
 14  \w   -158.00 -96.00   0.50  120.00    --  -90.00-125.00 -90.00  124
 15  \w    -53.00 -27.00   0.50  120.00    --  -90.00  57.00-150.00   52
 16  \w    -62.00 -18.00   0.50  120.00    --  -90.00  57.00  30.00   88
 17  \w     55.00 104.00   0.50  120.00    --  111.50 -99.00-180.00   98
 18  \w     42.00  68.00   0.50  120.00    --  111.50 -57.00 -60.00   52
 19  \w     44.00  97.00   0.50  120.00    --  111.50 -99.00 150.00  106
 20  \w     96.00 178.00   0.50  120.00    --  111.50 125.00  30.00  164
 21  \w     41.00  68.00   0.50  120.00    --  111.50 -57.00  90.00   54
 22  \w     40.00  68.00   0.50  120.00    --  111.50 -57.00 120.00   56
 23  \w    106.00 176.00   0.50  120.00    --  111.50  38.00-180.00  140
 24  \w    102.00 159.00   0.50  120.00    --  111.50  38.00 120.00  114
 25  \w     99.00 167.00   0.50  120.00    --  111.50  57.00 120.00  136
 26  \w     40.00  68.00   0.50  120.00    --  111.50 -57.00-180.00   56
 27  \w     40.00  68.00   0.50  120.00    --  111.50 -57.00-120.00   56
;
_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      -0.0224276000
_diffrn_orient_matrix_UB_12      0.0313161000
_diffrn_orient_matrix_UB_13      -0.0268520000
_diffrn_orient_matrix_UB_21      -0.1527519000
_diffrn_orient_matrix_UB_22      -0.0086538000
_diffrn_orient_matrix_UB_23      -0.0418963000
_diffrn_orient_matrix_UB_31      -0.0840694000
_diffrn_orient_matrix_UB_32      0.0072329000
_diffrn_orient_matrix_UB_33      0.0660759000
_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  0.0644
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            59178
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         2.557
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.519
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'intense orange'
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       needle
_exptl_crystal_F_000             3549
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1070
_refine_ls_number_reflns         13889
_refine_ls_number_restraints     480
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0769
_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^)+(0.1244P)^2^+10.8603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2159
_refine_ls_wR_factor_ref         0.2327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10106
_reflns_number_total             13889
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09017b2.cif
_cod_data_source_block           agor25_06
_cod_original_formula_sum        'C29 H27.17 Cu F12 N8.50 O2 P2'
_cod_database_code               7251737
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C29H27.5CuF12N7O3.5P2
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.667
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P4-F20 = P4-F22 = P4-F17 = P4-F18 = P4-F21 = P4-F19
 1.65 with sigma of 0.02
 N14-C44 = C44-C44A
 1.4 with sigma of 0.02
 C43-N13
 1.45 with sigma of 0.02
 N13-C43A
 1.45 with sigma of 0.02
 F20-F17 \\sim F22-F18 \\sim F19-F21
 with sigma of 0.05
 P4-F20 \\sim P4-F22 \\sim P4-F17 \\sim P4-F18 \\sim P4-F21 \\sim P4-F19
 with sigma of 0.02
 F20-F22 \\sim F20-F18 \\sim F20-F21 \\sim F20-F19 \\sim F17-F22 \\sim F17-F18
\\sim F17-F21 \\sim F17-F19
 with sigma of 0.04
 P4-F20 \\sim P4A-F22A
 with sigma of 0.02
 F17-F19 \\sim F19A-F21A
 with sigma of 0.04
 F22-F19 \\sim F17A-F21A
 with sigma of 0.04
 P4-F17 \\sim P4A-F19A
 with sigma of 0.02
 P4-F18 \\sim P4A-F20A
 with sigma of 0.02
 P4-F21 \\sim P4A-F18A
 with sigma of 0.02
 P4-F19 \\sim P4A-F21A
 with sigma of 0.02
 F22-F18 \\sim F17A-F20A
 with sigma of 0.04
 P4-F22 \\sim P4A-F17A
 with sigma of 0.02
 F17-F18 \\sim F19A-F20A
 with sigma of 0.04
 F18-F21 \\sim F20A-F18A
 with sigma of 0.04
 F22-F17 \\sim F17A-F19A
 with sigma of 0.04
 F22-F21 \\sim F17A-F18A
 with sigma of 0.04
 F17-F21 \\sim F19A-F18A
 with sigma of 0.04
 F18-F19 \\sim F20A-F21A
 with sigma of 0.04
 F20-F22 \\sim F22A-F17A
 with sigma of 0.04
 F21-F19 \\sim F18A-F21A
 with sigma of 0.04
 F20-F17 \\sim F22A-F19A
 with sigma of 0.04
 F20-F18 \\sim F22A-F20A
 with sigma of 0.04
 F20-F21 \\sim F22A-F18A
 with sigma of 0.04
 F20-F19 \\sim F22A-F21A
 with sigma of 0.04
 C44A-N13 \\sim C44-N13
 with sigma of 0.04
 C43A-N13 \\sim C43-N13
 with sigma of 0.02
 N14-C44A \\sim N14-C44
 with sigma of 0.02
 N14-C43A \\sim N14-C43
 with sigma of 0.04
 C44A-C43A \\sim C44-C43
 with sigma of 0.02
 C41A-N13 \\sim C41-N13
 with sigma of 0.02
 C41A-N14 \\sim C41-N14
 with sigma of 0.02
 C12-N4 \\sim C12-N4A
 with sigma of 0.02
 C14A-N4 \\sim C14-N4A
 with sigma of 0.04
 C16-C14A \\sim C16A-C14
 with sigma of 0.04
 N4-N5A \\sim N4A-N5
 with sigma of 0.04
 C15A-N5A \\sim C15-N5
 with sigma of 0.02
 C16-N4 \\sim C16A-N4A
 with sigma of 0.02
 C16-C13A \\sim C16A-C13
 with sigma of 0.04
 C16-N5A \\sim C16A-N5
 with sigma of 0.02
 C15A-C14A \\sim C15-C14
 with sigma of 0.04
 C14A-C13A \\sim C14-C13
 with sigma of 0.02
 C13A-N5A \\sim C13-N5
 with sigma of 0.04
 C14A-N5A \\sim C14-N5
 with sigma of 0.02
 C13A-N4 \\sim C13-N4A
 with sigma of 0.02
 C12-C16 \\sim C12-C16A
 with sigma of 0.04
 C12-C13A \\sim C12-C13
 with sigma of 0.04
 C16-C15A \\sim C16A-C15
 with sigma of 0.04
3. Rigid bond restraints
 N4, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
P4 \\sim F17 \\sim F18 \\sim F19 \\sim F20 \\sim F21 \\sim F22: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C44A) = Uanis(C44) = Uanis(C43) = Uanis(C43A) = Uanis(C54) = Uanis(C53)
Uanis(C15A) = Uanis(C15)
5. Rigid body (RIGU) restrains
 P4, F17, F18, F19, F20, F21, F22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N4, N4A, N5, N5A, C13, C13A, C14, C14A, C15, C15A, C16, C16A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P4, F17, F18, F19, F20, F21, F22, P4A, F17A, F18A, F19A, F20A, F21A, F22A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N16, C54, C55, C56
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(P4A)=Sof(F17A)=Sof(F18A)=Sof(F19A)=Sof(F20A)=Sof(F21A)=Sof(F22A)=1-FVAR(1)
 Sof(P4)=Sof(F17)=Sof(F18)=Sof(F19)=Sof(F20)=Sof(F21)=Sof(F22)=FVAR(1)
 Fixed Sof: H12C(0.67) H12D(0.67) H12A(0.33) H12B(0.33) C14A(0.67) C13A(0.67)
 H13A(0.67) N4A(0.67) C16A(0.67) H16A(0.67) N5A(0.67) C15(0.33) H15A(0.33)
 H15B(0.33) H15C(0.33) C15A(0.67) H15D(0.67) H15E(0.67) H15F(0.67) C16(0.33)
 H16(0.33) N4(0.33) C13(0.33) H13(0.33) C14(0.33) H14(0.33) N5(0.33) C41(0.5)
 H41(0.5) C41A(0.5) H41A(0.5) C44A(0.5) H44A(0.5) C43A(0.5) H43A(0.5) C43(0.5)
 H43(0.5) C44(0.5) H44(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C12(H12C,H12D), C12(H12A,H12B), C24(H24A,H24B), C40(H40A,H40B), C52(H52A,H52B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C11(H11), C13A(H13A), C16A(H16A),
 C16(H16), C13(H13), C14(H14), C17(H17), C20(H20), C21(H21), C23(H23), C25(H25),
  C27(H27), C28(H28), C30(H30), C31(H31), C33(H33), C36(H36), C37(H37),
 C39(H39), C41(H41), C41A(H41A), C44A(H44A), C43A(H43A), C43(H43), C44(H44),
 C45(H45), C47(H47), C48(H48), C50(H50), C53(H53), C54(H54), C56(H56)
7.c Fitted pentagon refined as free rotating group:
 C14A(C13A,N4A,C16A,N5A), C16(N4,C13,C14,N5), C41A(N14,C44A,C43A,N13)
7.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F), C26(H26A,H26B,H26C), C42(H42A,H42B,
 H42C), C55(H55A,H55B,H55C), C58(H58A,H58B,H58C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              35194
_shelx_fab_checksum              50996
_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 1.943
_oxdiff_exptl_absorpt_empirical_full_min 0.478