Direct Electrocatalytic O-O Coupling for Modular Synthesis of Aza-cyclic Peroxides from Paired Oxygen Donors
Yu, Cong; Wang, Liwei; Bu, Xiaotong; Liao, Hui; Gao, Meng; Green Chemistry  (2025) –; doi:10.1039/D5GC04553C

data_7251267
_publ_section_title
;
 Direct Electrocatalytic O-O Coupling for Modular Synthesis of Aza-cyclic
 Peroxides from Paired Oxygen Donors
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/D5GC04553C
_journal_year                    2025
_chemical_formula_moiety         '0.13(C14 H19 B N2 O4)'
_chemical_formula_sum            'C14 H17 B N2 O4'
_chemical_formula_weight         288.10
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-12-06 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.353(2)
_cell_angle_gamma                90
_cell_formula_units_Z            30
_cell_length_a                   12.0550(3)
_cell_length_b                   7.24310(10)
_cell_length_c                   18.7813(5)
_cell_measurement_reflns_used    5869
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2920
_cell_measurement_theta_min      3.9680
_cell_volume                     1588.71(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_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 0.977
_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    -21.00  39.00   0.50    0.05    --  -39.95  19.00 120.00  120
  2  \w   -124.00   8.00   0.50    0.05    --  -39.95 -19.00-150.00  264
  3  \w    -30.00  40.00   0.50    0.05    --  -39.95  37.00   0.00  140
  4  \w    100.00 126.00   0.50    0.05    --   39.95-178.00-150.00   52
  5  \w     77.00 122.00   0.50    0.05    --   39.95 178.00 -30.00   90
  6  \w    -26.00  26.00   0.50    0.05    --   39.95 -19.00 120.00  104
  7  \w     66.00 115.00   0.50    0.05    --   39.95-178.00 150.00   98
  8  \w    -51.00 -16.00   0.50    0.20    --  -94.50  45.00 -30.00   70
  9  \w   -170.00-129.00   0.50    0.20    --  -94.50 -77.00   0.00   82
 10  \w   -114.00 -68.00   0.50    0.20    --  -94.50 -77.00  30.00   92
 11  \w   -123.00 -76.00   0.50    0.20    --  -94.50-125.00  90.00   94
 12  \w   -164.00-130.00   0.50    0.20    --  -94.50 -77.00  30.00   68
 13  \w    -94.00 -65.00   0.50    0.20    --  -94.50 -77.00   0.00   58
 14  \w    -71.00 -20.00   0.50    0.20    --  -94.50  61.00-150.00  102
 15  \w   -167.00-141.00   0.50    0.20    --  -94.50-125.00  90.00   52
 16  \w    -51.00 -22.00   0.50    0.20    --  -94.50  45.00 -90.00   58
 17  \w    -50.00 -24.00   0.50    0.20    --  -94.50  45.00  90.00   52
 18  \w    -83.00 -27.00   0.50    0.20    --  -94.50 125.00   0.00  112
 19  \w     44.00  70.00   0.50    0.20    --  108.87 -77.00 -90.00   52
 20  \w    134.00 175.00   0.50    0.20    --  108.87   0.00 -30.00   82
 21  \w     38.00  69.00   0.50    0.20    --  108.87 -61.00 150.00   62
 22  \w     72.00 178.00   0.50    0.20    --  108.87  30.00  90.00  212
 23  \w     93.00 129.00   0.50    0.20    --  108.87-149.00 168.93   72
 24  \w     78.00 104.00   0.50    0.20    --  108.87 -94.00-120.00   52
 25  \w     31.00  56.00   0.50    0.20    --  108.87 -94.00-120.00   50
 26  \w     23.00 113.00   0.50    0.20    --  108.87   0.00 -30.00  180
 27  \w     50.00 105.00   0.50    0.20    --  108.87 -94.00 -60.00  110
 28  \w     75.00 153.00   0.50    0.20    --  108.87  30.00   0.00  156
 29  \w     39.00  66.00   0.50    0.20    --  108.87 -61.00  60.00   54
 30  \w     72.00  97.00   0.50    0.20    --  108.87 -77.00 -90.00   50
 31  \w     68.00 107.00   0.50    0.20    --  108.87-125.00  90.00   78
 32  \w     40.00  92.00   0.50    0.20    --  108.87 -94.00   0.00  104
 33  \w     34.00  71.00   0.50    0.20    --  108.87 -61.00  90.00   74
 34  \w     41.00  92.00   0.50    0.20    --  108.87-125.00-180.00  102
 35  \w     69.00  95.00   0.50    0.20    --  108.87 -94.00-150.00   52
 36  \w     34.00  59.00   0.50    0.20    --  108.87 -61.00-120.00   50
 37  \w     33.00  59.00   0.50    0.20    --  108.87 -94.00-150.00   52
 38  \w     40.00  65.00   0.50    0.20    --  108.87 -61.00-150.00   50
 39  \w     63.00  85.00   0.50    0.20    --  108.87-149.00 168.93   44
;
_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      0.0707234000
_diffrn_orient_matrix_UB_12      0.0691523000
_diffrn_orient_matrix_UB_13      0.0751826000
_diffrn_orient_matrix_UB_21      -0.1030154000
_diffrn_orient_matrix_UB_22      -0.0338714000
_diffrn_orient_matrix_UB_23      0.0331041000
_diffrn_orient_matrix_UB_31      0.0423552000
_diffrn_orient_matrix_UB_32      -0.1982847000
_diffrn_orient_matrix_UB_33      0.0204429000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13907
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.952
_diffrn_reflns_theta_min         3.959
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.426
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    9.034
_exptl_crystal_F_000             4560
_refine_diff_density_max         1.882
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.709
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.709
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.1144
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3687
_refine_ls_wR_factor_ref         0.3910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2548
_reflns_number_total             3140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04553c2.cif
_cod_data_source_block           20241129-yc
_cod_database_code               7251267
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00G(H00A,H00B,H00C), C00J(H00G,H00J,H00K), C00K(H00L,H00M,H00N)
;
_shelx_res_checksum              87764
_shelx_hkl_checksum              90154
_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 6.651
_oxdiff_exptl_absorpt_empirical_full_min 0.406