Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.
Siu, Juno C.; Parry, Joseph B.; Lin, Song; Journal of the American Chemical Society 141 (2019) 2825–2831; doi:10.1021/jacs.8b13192

data_4128439
_publ_section_title
;
 Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a
 Metastable Charge-Transfer Complex.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2825
_journal_page_last               2831
_journal_paper_doi               10.1021/jacs.8b13192
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C17 H29 N2 O2, H2 O'
_chemical_formula_sum            'C17 H31 N2 O3'
_chemical_formula_weight         311.44
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-02
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.4620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.98340(10)
_cell_length_b                   10.83800(10)
_cell_length_c                   11.62230(10)
_cell_measurement_reflns_used    12525
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.7850
_cell_measurement_theta_min      3.1720
_cell_volume                     1746.47(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_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      1.00  53.00   0.50    0.46    --   48.42 -72.00  33.00  104
  2  \w     82.00 113.00   0.50    1.82    --  107.75 -72.00  33.00   62
  3  \w     94.00 123.00   0.50    1.82    --  107.75 -61.00 120.00   58
  4  \w    126.00 166.00   0.50    1.82    --  107.75   0.00  60.00   80
  5  \w    133.00 175.00   0.50    1.82    --  107.75  30.00  90.00   84
  6  \w    143.00 169.00   0.50    1.82    --  107.75  77.00  90.00   52
  7  \w    143.00 169.00   0.50    1.82    --  107.75 125.00  30.00   52
  8  \w    129.00 155.00   0.50    1.82    --  107.75  45.00 -30.00   52
  9  \w    121.00 172.00   0.50    1.82    --  107.75  30.00-120.00  102
 10  \w    151.00 177.00   0.50    1.82    --  107.75  77.00-150.00   52
 11  \w     76.00 102.00   0.50    1.82    --  107.75   0.00  60.00   52
 12  \w    129.00 155.00   0.50    1.82    --  107.75  15.00 120.00   52
 13  \w    113.00 171.00   0.50    1.82    --  107.75  72.00 163.00  116
 14  \w    122.00 178.00   0.50    1.82    --  107.75 125.00 150.00  112
 15  \w     98.00 177.00   0.50    1.82    --  107.75  45.00 150.00  158
 16  \w    105.00 131.00   0.50    1.82    --  107.75  30.00  90.00   52
 17  \w     92.00 117.00   0.50    1.82    --  107.75  77.00  90.00   50
 18  \w     50.00  75.00   0.50    0.46    --   48.42  72.00 163.00   50
 19  \w     40.00  70.00   0.50    1.82    --  107.75 -19.00 173.36   60
 20  \w     74.00 110.00   0.50    1.82    --  107.75 -19.00 173.36   72
 21  \w     61.00  88.00   0.50    1.82    --  107.75 -61.00 120.00   54
 22  \w     81.00 108.00   0.50    1.82    --  107.75 -79.00  82.59   54
 23  \w     53.00  79.00   0.50    1.82    --  107.75 -79.00  82.59   52
 24  \w     40.00  66.00   0.50    1.82    --  107.75 -72.00  33.00   52
 25  \w     37.00  69.00   0.50    1.82    --  107.75 -30.00  90.00   64
 26  \w     38.00  64.00   0.50    1.82    --  107.75   0.00  60.00   52
 27  \w     38.00  67.00   0.50    1.82    --  107.75 -30.00  60.00   58
 28  \w     35.00  68.00   0.50    1.82    --  107.75 -30.00   0.00   66
 29  \w     37.00  66.00   0.50    1.82    --  107.75 -45.00 -90.00   58
 30  \w     36.00  65.00   0.50    1.82    --  107.75 -30.00-150.00   58
 31  \w     36.00  76.00   0.50    1.82    --  107.75 -45.00-180.00   80
 32  \w     39.00  68.00   0.50    1.82    --  107.75 -94.00-180.00   58
 33  \w     83.00 116.00   0.50    1.82    --  107.75-125.00-120.00   66
 34  \w     42.00  67.00   0.50    1.82    --  107.75-125.00   0.00   50
 35  \w     36.00  89.00   0.50    1.82    --  107.75 -94.00  90.00  106
 36  \w     46.00  72.00   0.50    1.82    --  107.75-125.00 150.00   52
 37  \w     39.00  96.00   0.50    1.82    --  107.75 -77.00  97.13  114
 38  \w    -68.00  12.00   0.50    0.46    --  -48.42  72.00 163.00  160
 39  \w    -84.00 -59.00   0.50    1.82    --  -86.25  72.00 163.00   50
 40  \w    -64.00 -38.00   0.50    1.82    --  -86.25  30.00  30.00   52
 41  \w   -118.00 -30.00   0.50    0.46    --  -48.42 -72.00  33.00  176
 42  \w   -118.00 -87.00   0.50    0.46    --  -48.42-125.00-150.00   62
 43  \w   -115.00 -70.00   0.50    0.46    --  -48.42-125.00-180.00   90
 44  \w   -136.00-111.00   0.50    1.82    --  -86.25 -72.00  33.00   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      0.0971577000
_diffrn_orient_matrix_UB_12      0.0165698000
_diffrn_orient_matrix_UB_13      -0.0472637000
_diffrn_orient_matrix_UB_21      -0.0224698000
_diffrn_orient_matrix_UB_22      -0.1129167000
_diffrn_orient_matrix_UB_23      -0.0794856000
_diffrn_orient_matrix_UB_31      -0.0490429000
_diffrn_orient_matrix_UB_32      0.0846935000
_diffrn_orient_matrix_UB_33      -0.0965422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20024
_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         77.810
_diffrn_reflns_theta_min         3.187
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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 orange'
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0459P)^2^+0.6115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3459
_reflns_number_total             3726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13192_si_002.cif
_cod_data_source_block           rjp1_abs
_cod_database_code               4128439
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C17H31N2O2
_chemical_oxdiff_usercomment     'Crystallized from acetonitrile.'
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.91 with sigma of 0.02
 O3-H3A = O3-H3B
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
  C15(H15A,H15B)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              23495
_shelx_hkl_checksum              11578
_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 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.683