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_7251266
_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         'C14 H15 I N2 O4'
_chemical_formula_sum            'C14 H15 I N2 O4'
_chemical_formula_weight         402.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-07-26 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6028(19)
_cell_length_b                   6.5055(6)
_cell_length_c                   25.387(2)
_cell_measurement_reflns_used    8648
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5650
_cell_measurement_theta_min      2.2370
_cell_volume                     3237.5(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.972
_diffrn_measured_fraction_theta_max 0.888
_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     46.00  71.00   0.50    0.80    --  108.87 -61.00  30.00   50
  2  \w     39.00  65.00   0.50    0.80    --  108.87 -61.00  60.00   52
  3  \w     39.00  64.00   0.50    0.80    --  108.87 -61.00  90.00   50
  4  \w     35.00  61.00   0.50    0.80    --  108.87 -61.00 150.00   52
  5  \w    -27.00  40.00   0.50    0.20    --  -39.95  19.00  60.00  134
  6  \w    -68.00 -42.00   0.50    0.80    --  -94.50  61.00  30.00   52
  7  \w    -65.00 -40.00   0.50    0.80    --  -94.50  61.00   0.00   50
  8  \w    -40.00 -15.00   0.50    0.80    --  -94.50  35.00 -17.00   50
  9  \w    -16.00   9.00   0.50    0.20    --  -39.95  35.00 -17.00   50
 10  \w    -50.00 -24.00   0.50    0.80    --  -94.50  45.00-120.00   52
 11  \w    -51.00 -25.00   0.50    0.80    --  -94.50  45.00-150.00   52
 12  \w    -45.00 -20.00   0.50    0.80    --  -94.50  45.00-180.00   50
 13  \w   -174.00-109.00   0.50    0.80    --  -94.50 -35.00-175.00  130
 14  \w    -79.00 -51.00   0.50    0.80    --  -94.50  91.00 168.00   56
 15  \w     30.00  70.00   0.50    0.80    --  108.87 -94.00   0.00   80
 16  \w     32.00  85.00   0.50    0.80    --  108.87-112.00 -29.00  106
 17  \w     80.00 105.00   0.50    0.80    --  108.87 -94.00   0.00   50
 18  \w     46.00  71.00   0.50    0.20    --   39.95-112.00 -29.00   50
 19  \w      8.00  83.00   0.50    0.20    --   39.95 -99.00-120.00  150
 20  \w    -83.00 -57.00   0.50    0.20    --  -39.95 153.00-141.00   52
 21  \w    -54.00 -19.00   0.50    0.80    --  -94.50 125.00  60.00   70
 22  \w     81.00 177.00   0.50    0.80    --  108.87  30.00 -30.00  192
 23  \w     41.00  67.00   0.50    0.80    --  108.87 -77.00   0.00   52
 24  \w     73.00  99.00   0.50    0.80    --  108.87 -77.00   0.00   52
 25  \w     34.00  60.00   0.50    0.80    --  108.87-125.00-180.00   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      0.0261217000
_diffrn_orient_matrix_UB_12      0.0070881000
_diffrn_orient_matrix_UB_13      0.0572946000
_diffrn_orient_matrix_UB_21      -0.0669905000
_diffrn_orient_matrix_UB_22      -0.0990538000
_diffrn_orient_matrix_UB_23      0.0191431000
_diffrn_orient_matrix_UB_31      0.0317217000
_diffrn_orient_matrix_UB_32      -0.2147859000
_diffrn_orient_matrix_UB_33      -0.0068288000
_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  0.1210
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11783
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.246
_diffrn_reflns_theta_min         3.482
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.923
_refine_diff_density_min         -1.985
_refine_diff_density_rms         0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0977
_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^)+(0.1911P)^2^+6.8457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2722
_refine_ls_wR_factor_ref         0.2910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2546
_reflns_number_total             3052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04553c2.cif
_cod_data_source_block           20240724-yc
_cod_database_code               7251266
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.303
_shelx_estimated_absorpt_t_min   0.255
_reflns_odcompleteness_completeness 97.10
_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. Restrained distances
 H8C-H9B
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4327
_shelx_hkl_checksum              5956
_shelx_fab_checksum              9178
_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 4.046
_oxdiff_exptl_absorpt_empirical_full_min 0.422