Synthesis of unsymmetrical bisperoxides <i>via</i> semicarbazone ozonolysis in the presence of hydroperoxides.
Budekhin, Roman A.; Sliguzova, Darya Yu; Fomenkov, Dmitri I.; Baranin, Sergei V.; Terent'ev, Alexander O.; Organic & biomolecular chemistry 23 (2025) 8259–8266; doi:10.1039/d5ob01159k

data_7160692
_publ_section_title
;
 Synthesis of unsymmetrical bisperoxides <i>via</i> semicarbazone
 ozonolysis in the presence of hydroperoxides.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8259
_journal_page_last               8266
_journal_paper_doi               10.1039/d5ob01159k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C14 H24 O4'
_chemical_formula_sum            'C14 H24 O4'
_chemical_formula_weight         256.33
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-12-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-23 deposited with the CCDC.	2025-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9112(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.37131(4)
_cell_length_b                   22.56666(17)
_cell_length_c                   19.24769(13)
_cell_measurement_reflns_used    29018
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.4200
_cell_measurement_theta_min      3.0220
_cell_volume                     2752.70(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 1.000
_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    -80.00  14.00   0.50    0.86    --  -44.24 102.00 -13.00  188
  2  \w      8.00  82.00   0.50    0.86    --   44.24-102.00-115.00  148
  3  \w      8.00  82.00   0.50    0.86    --   44.24-102.00-115.00  148
  4  \w    -81.00 -24.00   0.50    3.44    --  -96.00 102.00 -13.00  114
  5  \w     46.00 107.00   0.50    3.44    --  117.50-102.00-115.00  122
  6  \w    106.00 178.00   0.50    3.44    --  117.50 102.00 -13.00  144
  7  \w    -27.00  35.00   0.50    0.86    --  -44.24  19.00 -30.00  124
  8  \w    -27.00  35.00   0.50    0.86    --  -44.24  19.00  90.00  124
  9  \w     12.00  43.00   0.50    0.86    --   44.24  88.00  92.20   62
 10  \w     34.00  94.00   0.50    0.86    --   44.24-125.00-180.00  120
 11  \w    -34.00  27.00   0.50    0.86    --   44.24 -19.00-150.00  122
 12  \w     12.00  43.00   0.50    0.86    --   44.24  89.00  37.84   62
 13  \w     34.00  94.00   0.50    0.86    --   44.24-125.00-180.00  120
 14  \w    -51.00 -21.00   0.50    3.44    --  -96.00  45.00-180.00   60
 15  \w   -168.00 -85.00   0.50    3.44    --  -96.00-102.00-115.00  166
 16  \w     45.00  71.00   0.50    3.44    --  117.50 -61.00 150.00   52
 17  \w     45.00  71.00   0.50    3.44    --  117.50 -61.00-120.00   52
 18  \w     97.00 178.00   0.50    3.44    --  117.50  61.00 -30.00  162
 19  \w     45.00 149.00   0.50    3.44    --  117.50 -87.00 -76.12  208
 20  \w     98.00 178.00   0.50    3.44    --  117.50  30.00 120.00  160
 21  \w     45.00  71.00   0.50    3.44    --  117.50 -61.00 -60.00   52
 22  \w     47.00 111.00   0.50    3.44    --  117.50-125.00 150.00  128
 23  \w     47.00 111.00   0.50    3.44    --  117.50-125.00   0.00  128
 24  \w     95.00 178.00   0.50    3.44    --  117.50 125.00 120.00  166
 25  \w     98.00 178.00   0.50    3.44    --  117.50  45.00 -60.00  160
 26  \w     47.00 111.00   0.50    3.44    --  117.50-125.00  30.00  128
 27  \w     91.00 142.00   0.50    3.44    --  117.50  77.00-180.00  102
 28  \w    149.00 175.00   0.50    3.44    --  117.50  77.00-180.00   52
 29  \w     49.00  91.00   0.50    3.44    --  117.50-125.00-180.00   84
 30  \w     95.00 147.00   0.50    3.44    --  117.50 125.00-150.00  104
 31  \w     73.00 119.00   0.50    3.44    --  117.50 -83.00-105.36   92
 32  \w     46.00  71.00   0.50    3.44    --  117.50 -77.00 -60.00   50
 33  \w     59.00 102.00   0.50    3.44    --  117.50 -95.00  30.00   86
 34  \w     99.00 130.00   0.50    3.44    --  117.50  30.00   0.00   62
 35  \w    149.00 174.00   0.50    3.44    --  117.50  30.00   0.00   50
 36  \w    120.00 171.00   0.50    3.44    --  117.50  61.00-150.00  102
 37  \w     51.00 101.00   0.50    3.44    --  117.50-102.00-101.87  100
 38  \w     67.00  93.00   0.50    3.44    --  117.50 -95.00-120.00   52
 39  \w     55.00 105.00   0.50    3.44    --  117.50 -77.00  30.00  100
 40  \w     62.00  88.00   0.50    3.44    --  117.50 -95.00  90.00   52
 41  \w     98.00 177.00   0.50    3.44    --  117.50  45.00  60.00  158
 42  \w    100.00 144.00   0.50    3.44    --  117.50 -80.00  86.84   88
 43  \w     47.00  88.00   0.50    3.44    --  117.50 -80.00  86.84   82
 44  \w     53.00  79.00   0.50    3.44    --  117.50-125.00-150.00   52
 45  \w     47.00 107.00   0.50    3.44    --  117.50-104.00 -48.73  120
 46  \w     49.00  90.00   0.50    3.44    --  117.50 -95.00 -90.00   82
 47  \w     98.00 128.00   0.50    3.44    --  117.50  45.00  30.00   60
 48  \w    111.00 137.00   0.50    3.44    --  117.50  30.00-180.00   52
 49  \w    113.00 139.00   0.50    3.44    --  117.50  77.00-150.00   52
 50  \w    104.00 174.00   0.50    3.44    --  117.50  77.00 -90.00  140
 51  \w    133.00 174.00   0.50    3.44    --  117.50  15.00 -30.00   82
 52  \w     90.00 116.00   0.50    3.44    --  117.50  15.00  30.00   52
 53  \w    112.00 150.00   0.50    3.44    --  117.50 -88.00-111.35   76
 54  \w    111.00 148.00   0.50    3.44    --  117.50 -88.00 169.97   74
 55  \w     45.00  70.00   0.50    3.44    --  117.50 -61.00 120.00   50
;
_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      0.0573925000
_diffrn_orient_matrix_UB_12      -0.0282879000
_diffrn_orient_matrix_UB_13      -0.0683868000
_diffrn_orient_matrix_UB_21      -0.0493893000
_diffrn_orient_matrix_UB_22      0.0589568000
_diffrn_orient_matrix_UB_23      -0.0386508000
_diffrn_orient_matrix_UB_31      0.2309718000
_diffrn_orient_matrix_UB_32      0.0196267000
_diffrn_orient_matrix_UB_33      0.0174369000
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            44051
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.798
_diffrn_reflns_theta_min         3.027
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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            'clear colourless'
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0567P)^2^+0.6406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5586
_reflns_number_total             6027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01159k3.cif
_cod_data_source_block           24pnv_r05_g
_cod_depositor_comments          'Adding full bibliography for 7160692.cif.'
_cod_database_code               7160692
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H24 O4'
_chemical_oxdiff_usercomment     DS-153
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.683
_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 Ternary CH refined with riding coordinates:
 C2A(H1), C4A(H4A), C6A(H6A), C9A(H9A), C2B(H2C), C4B(H4B), C6B(H6B), C9B(H9B)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3A,H3B), C5A(H5A,H5B), C7A(H7A,H7B), C8A(H8A,H8B), C10A(H10A,H10B),
 C3B(H3C,H3D), C5B(H5C,H5D), C7B(H7C,H7D), C8B(H8C,H8D), C10B(H10C,H10D)
2.c Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C12B(H12D,
 H12E,H12F), C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F)
;
_shelx_res_checksum              37275
_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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.747