Electrochemical Two-electron Oxygen Reduction Reaction (ORR) Induced Aerobic Oxidation of α- Diazoesters
Ruan, Mengyao; Chen, Liang; Wen, ziyang; Yang, Fan; Ma, Chao; Lu, Cuifen; Yang, Guichun; Gao, Meng; Chemical Communications  (2022) –; doi:10.1039/D1CC06945D

data_7129589
_publ_section_title
;
 Electrochemical Two-electron Oxygen Reduction Reaction (ORR) Induced
 Aerobic Oxidation of \a- Diazoesters
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06945D
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C28 H34 O4'
_chemical_formula_sum            'C28 H34 O4'
_chemical_formula_weight         434.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-27 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.339(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7004(2)
_cell_length_b                   18.4346(3)
_cell_length_c                   10.0905(2)
_cell_measurement_reflns_used    7643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4170
_cell_measurement_theta_min      4.5850
_cell_volume                     1189.73(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_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    100.00 176.00   0.50    0.28    --  112.45 111.00   0.00  152
  2  \w    102.00 170.00   0.50    0.28    --  112.45 111.00 150.00  136
  3  \w     63.00 125.00   0.50    0.28    --   37.97 178.00  60.00  124
  4  \w     61.00 124.00   0.50    0.28    --   37.97 178.00 -60.00  126
  5  \w     62.00  87.00   0.50    0.28    --  112.45 178.00-180.00   50
  6  \w     90.00 148.00   0.50    0.28    --  112.45 178.00-180.00  116
  7  \w    101.00 151.00   0.50    0.28    --  112.45  68.00  13.00  100
  8  \w     48.00 108.00   0.50    0.28    --   37.97  68.00  13.00  120
  9  \w    -10.00  26.00   0.50    0.28    --   37.97  97.00  24.72   72
 10  \w   -129.00 -96.00   0.50    0.28    --  -98.50 178.00  30.00   66
 11  \w   -113.00 -66.00   0.50    0.28    --  -37.97 -68.00-120.00   94
 12  \w   -106.00 -80.00   0.50    0.28    --  -37.97 -77.00 -30.00   52
 13  \w    -62.00  -5.00   0.50    0.28    --  -37.97 -68.00-120.00  114
 14  \w    -74.00   0.00   0.50    0.28    --  -37.97 -77.00 -30.00  148
 15  \w   -117.00 -45.00   0.50    0.28    --  -37.97 -77.00  90.00  144
 16  \w    -42.00  -1.00   0.50    0.28    --  -37.97 -77.00  90.00   82
 17  \w    -51.00 -15.00   0.50    0.28    --  -37.97 -57.00 120.00   72
 18  \w   -110.00 -55.00   0.50    0.28    --  -37.97 -57.00 120.00  110
 19  \w   -168.00 -67.00   0.50    0.28    --  -98.50 -61.00 -30.00  202
 20  \w    -99.00 -70.00   0.50    0.28    --  -98.50 -54.00   5.76   58
 21  \w    -92.00 -60.00   0.50    0.28    --  -98.50 -77.00 -90.00   64
 22  \w   -143.00 -64.00   0.50    0.28    --  -98.50 -68.00-120.00  158
 23  \w   -174.00-148.00   0.50    0.28    --  -98.50 -68.00-120.00   52
 24  \w   -160.00-103.00   0.50    0.28    --  -98.50 -77.00 -90.00  114
 25  \w   -176.00-132.00   0.50    0.28    --  -98.50 -54.00   5.76   88
 26  \w   -172.00-118.00   0.50    0.28    --  -98.50 -61.00 144.11  108
 27  \w   -114.00 -67.00   0.50    0.28    --  -98.50 -61.00 144.11   94
 28  \w    -90.00 -62.00   0.50    0.28    --  -98.50 -74.00  99.20   56
 29  \w   -153.00 -61.00   0.50    0.28    --  -98.50 -76.00 123.49  184
 30  \w   -176.00-107.00   0.50    0.28    --  -98.50 -78.00  46.23  138
 31  \w   -174.00 -59.00   0.50    0.28    --  -98.50 -80.00  23.62  230
 32  \w    -92.00 -60.00   0.50    0.28    --  -98.50 -77.00 113.14   64
 33  \w    -93.00 -62.00   0.50    0.28    --  -98.50 -77.00  60.00   62
 34  \w    -85.00 -60.00   0.50    0.28    --  -98.50 -77.00 150.00   50
 35  \w   -140.00-115.00   0.50    0.28    --  -98.50 -77.00 113.14   50
 36  \w   -144.00 -60.00   0.50    0.28    --  -98.50 -77.00  90.00  168
 37  \w    -92.00 -59.00   0.50    0.28    --  -98.50 -80.00  79.98   66
 38  \w   -163.00-138.00   0.50    0.28    --  -98.50 -77.00 150.00   50
 39  \w   -144.00 -60.00   0.50    0.28    --  -98.50 -77.00 -37.93  168
 40  \w    -85.00 -60.00   0.50    0.28    --  -98.50 -78.00 -45.05   50
 41  \w   -108.00 -60.00   0.50    0.28    --  -98.50 -77.00-138.40   96
 42  \w    -93.00 -60.00   0.50    0.28    --  -98.50 -77.00-150.00   66
 43  \w   -176.00 -59.00   0.50    0.28    --  -98.50 -80.00-160.51  234
 44  \w   -174.00-106.00   0.50    0.28    --  -98.50 -77.00-180.00  136
 45  \w   -152.00-127.00   0.50    0.28    --  -98.50 -77.00-138.40   50
 46  \w   -150.00-125.00   0.50    0.28    --  -98.50 -74.00-100.42   50
 47  \w   -100.00 -60.00   0.50    0.28    --  -98.50 -77.00-180.00   80
 48  \w   -102.00 -61.00   0.50    0.28    --  -98.50 -74.00-100.42   82
 49  \w    -85.00 -60.00   0.50    0.28    --  -98.50 -78.00  46.23   50
 50  \w   -170.00-141.00   0.50    0.28    --  -98.50 -80.00  79.98   58
 51  \w   -121.00 -95.00   0.50    0.28    --  -98.50 -83.00   8.44   52
 52  \w    -83.00 -58.00   0.50    0.28    --  -98.50 -83.00 145.88   50
 53  \w    -65.00  39.00   0.50    0.28    --  -37.97  57.00 150.00  208
 54  \w     -7.00  18.00   0.50    0.28    --  -37.97  57.00  90.00   50
 55  \w    -52.00 -12.00   0.50    0.28    --  -37.97  57.00  90.00   80
 56  \w    -53.00  19.00   0.50    0.28    --  -37.97  68.00  13.00  144
 57  \w   -102.00 -77.00   0.50    0.28    --  -98.50  68.00  13.00   50
 58  \w   -119.00 -94.00   0.50    0.28    --  -98.50 -81.00-116.39   50
 59  \w      9.00  34.00   0.50    0.07    --    0.00 -68.00-120.00   50
 60  \w    -79.00  -6.00   0.50    0.28    --  -37.97 -77.00-150.00  146
 61  \w    -34.00  -9.00   0.50    0.28    --   37.97 -68.00-120.00   50
 62  \w     38.00  74.00   0.50    0.28    --  112.45 -68.00-120.00   72
 63  \w     84.00 110.00   0.50    0.28    --  112.45 -68.00-120.00   52
 64  \w     45.00 115.00   0.50    0.28    --  112.45-111.00-150.00  140
 65  \w     30.00 113.00   0.50    0.28    --  112.45-111.00   0.00  166
 66  \w     79.00 112.00   0.50    0.28    --  112.45-111.00 150.00   66
 67  \w     35.00  70.00   0.50    0.28    --  112.45-111.00 150.00   70
 68  \w   -121.00 -58.00   0.50    0.28    --  -98.50 -81.00 -56.21  126
 69  \w   -174.00 -58.00   0.50    0.28    --  -98.50 -81.00 -70.21  232
 70  \w   -165.00-139.00   0.50    0.28    --  -98.50 -81.00 -56.21   52
 71  \w    -84.00 -59.00   0.50    0.28    --  -98.50 -81.00-116.39   50
 72  \w    -83.00 -58.00   0.50    0.28    --  -98.50 -83.00   8.44   50
 73  \w   -169.00-143.00   0.50    0.28    --  -98.50 -83.00 145.88   52
 74  \w   -128.00-103.00   0.50    0.28    --  -98.50 -83.00 145.88   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      -0.1202954000
_diffrn_orient_matrix_UB_12      0.0382534000
_diffrn_orient_matrix_UB_13      -0.1361217000
_diffrn_orient_matrix_UB_21      0.1002139000
_diffrn_orient_matrix_UB_22      -0.0516554000
_diffrn_orient_matrix_UB_23      -0.0819779000
_diffrn_orient_matrix_UB_31      -0.1830192000
_diffrn_orient_matrix_UB_32      -0.0534254000
_diffrn_orient_matrix_UB_33      -0.0181924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21091
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.021
_diffrn_reflns_theta_min         4.591
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4507
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0610P)^2^+0.0534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                4178
_reflns_number_total             4507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06945d2.cif
_cod_data_source_block           7878
_cod_database_code               7129589
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 100.00
_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 Ternary CH refined with riding coordinates:
 C9(H9), C8(H8), C5(H5), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C10(H10A,H10B), C7(H7A,H7B), C14(H14A,H14B), C6(H6A,H6B),
 C1(H1A,H1B), C15(H15A,H15B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C24(H24), C23(H23), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              56225
_shelx_hkl_checksum              30101
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.714