Electrochemical Azidooxygenation of Alkenes Mediated by a TEMPO-N<sub>3</sub> Charge-Transfer Complex.
Siu, Juno C.; Sauer, Gregory S.; Saha, Ambarneil; Macey, Reed L.; Fu, Niankai; Chauviré, Timothée; Lancaster, Kyle M.; Lin, Song; Journal of the American Chemical Society 140 (2018) 12511–12520; doi:10.1021/jacs.8b06744

data_4132810
_publ_section_title
;
 Electrochemical Azidooxygenation of Alkenes Mediated by a
 TEMPO-N<sub>3</sub> Charge-Transfer Complex.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12511
_journal_page_last               12520
_journal_paper_doi               10.1021/jacs.8b06744
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C23 H30 N4 O'
_chemical_formula_sum            'C23 H30 N4 O'
_chemical_formula_weight         378.51
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-01
_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                 93.5250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.88010(10)
_cell_length_b                   14.63750(10)
_cell_length_c                   11.22330(10)
_cell_measurement_reflns_used    60158
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.7350
_cell_measurement_theta_min      3.4230
_cell_volume                     2111.95(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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 1.000
_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     14.00  57.00   0.50    0.94    --   48.42 -37.00 104.00   86
  2  \w     42.00  91.00   0.50    0.94    --   48.42  19.00  30.00   98
  3  \w     96.00 121.00   0.50    0.94    --   48.42  19.00  30.00   50
  4  \w     79.00 120.00   0.50    0.94    --   48.42  77.00  60.00   82
  5  \w     82.00 108.00   0.50    0.94    --   48.42  77.00 120.00   52
  6  \w     40.00  67.00   0.50    0.94    --   48.42  37.00  90.00   54
  7  \w     36.00  63.00   0.50    0.94    --   48.42  57.00  60.00   54
  8  \w     27.00  65.00   0.50    0.94    --   48.42  77.00  60.00   76
  9  \w     27.00  59.00   0.50    0.94    --   48.42  77.00 120.00   64
 10  \w     27.00  63.00   0.50    0.94    --   48.42  77.00   0.00   72
 11  \w     27.00  55.00   0.50    0.94    --   48.42  77.00 -30.00   56
 12  \w     27.00  58.00   0.50    0.94    --   48.42  77.00 -90.00   62
 13  \w     41.00 119.00   0.50    0.94    --   48.42  37.00 -99.00  156
 14  \w     80.00 119.00   0.50    0.94    --   48.42  77.00-180.00   78
 15  \w    102.00 158.00   0.50    3.75    --  107.75  37.00 -99.00  112
 16  \w    135.00 178.00   0.50    3.75    --  107.75  77.00 -90.00   86
 17  \w    148.00 174.00   0.50    3.75    --  107.75  66.00 -41.08   52
 18  \w    143.00 176.00   0.50    3.75    --  107.75  77.00 -30.00   66
 19  \w    148.00 175.00   0.50    3.75    --  107.75  61.00 -60.00   54
 20  \w    135.00 161.00   0.50    3.75    --  107.75  81.00  41.26   52
 21  \w    135.00 176.00   0.50    3.75    --  107.75  61.00  30.00   82
 22  \w    151.00 177.00   0.50    3.75    --  107.75  61.00  90.00   52
 23  \w    138.00 164.00   0.50    3.75    --  107.75  74.00 139.49   52
 24  \w    140.00 171.00   0.50    3.75    --  107.75  79.00 161.02   62
 25  \w    125.00 171.00   0.50    3.75    --  107.75  45.00  60.00   92
 26  \w    128.00 154.00   0.50    3.75    --  107.75  61.00   0.00   52
 27  \w    125.00 170.00   0.50    3.75    --  107.75  83.00  -1.09   90
 28  \w    126.00 152.00   0.50    3.75    --  107.75  77.00  30.00   52
 29  \w    137.00 177.00   0.50    3.75    --  107.75  30.00  30.00   80
 30  \w    109.00 154.00   0.50    3.75    --  107.75  45.00 -60.00   90
 31  \w    129.00 176.00   0.50    3.75    --  107.75  77.00-120.00   94
 32  \w    147.00 173.00   0.50    3.75    --  107.75  80.00-162.22   52
 33  \w    138.00 178.00   0.50    3.75    --  107.75  77.00-180.00   80
 34  \w    141.00 177.00   0.50    3.75    --  107.75  45.00-150.00   72
 35  \w    145.00 172.00   0.50    3.75    --  107.75  15.00-150.00   54
 36  \w    127.00 153.00   0.50    3.75    --  107.75  71.00-163.20   52
 37  \w     99.00 155.00   0.50    3.75    --  107.75  61.00 -90.00  112
 38  \w    103.00 137.00   0.50    3.75    --  107.75  45.00-150.00   68
 39  \w     94.00 151.00   0.50    3.75    --  107.75  61.00-120.00  114
 40  \w    103.00 139.00   0.50    3.75    --  107.75  15.00-150.00   72
 41  \w     86.00 113.00   0.50    3.75    --  107.75  77.00 -90.00   54
 42  \w     86.00 161.00   0.50    3.75    --  107.75  77.00 -60.00  150
 43  \w    136.00 175.00   0.50    3.75    --  107.75 125.00 -60.00   78
 44  \w     93.00 120.00   0.50    3.75    --  107.75  61.00   0.00   54
 45  \w     93.00 135.00   0.50    3.75    --  107.75  66.00 -41.08   84
 46  \w     99.00 130.00   0.50    3.75    --  107.75  61.00  30.00   62
 47  \w    100.00 128.00   0.50    3.75    --  107.75  30.00  30.00   56
 48  \w     87.00 122.00   0.50    3.75    --  107.75  81.00  41.26   70
 49  \w     93.00 120.00   0.50    3.75    --  107.75  61.00  90.00   54
 50  \w     95.00 177.00   0.50    3.75    --  107.75  61.00 120.00  164
 51  \w     87.00 113.00   0.50    3.75    --  107.75  74.00 139.49   52
 52  \w     86.00 141.00   0.50    3.75    --  107.75  77.00 120.00  110
 53  \w     87.00 166.00   0.50    3.75    --  107.75  77.00  60.00  158
 54  \w     86.00 112.00   0.50    3.75    --  107.75  77.00 -30.00   52
 55  \w     93.00 131.00   0.50    3.75    --  107.75  61.00 -60.00   76
 56  \w     87.00 123.00   0.50    3.75    --  107.75  77.00-120.00   72
 57  \w     89.00 121.00   0.50    3.75    --  107.75  71.00-163.20   64
 58  \w     86.00 112.00   0.50    3.75    --  107.75  77.00-180.00   52
 59  \w     89.00 149.00   0.50    3.75    --  107.75  77.00-150.00  120
 60  \w     93.00 125.00   0.50    3.75    --  107.75 125.00 -60.00   64
 61  \w     84.00 112.00   0.50    3.75    --  107.75  83.00  -1.09   56
 62  \w     87.00 112.00   0.50    3.75    --  107.75  77.00  30.00   50
 63  \w     86.00 124.00   0.50    3.75    --  107.75  77.00   0.00   76
 64  \w     86.00 144.00   0.50    3.75    --  107.75  77.00  90.00  116
 65  \w     93.00 143.00   0.50    3.75    --  107.75  61.00 150.00  100
 66  \w     87.00 170.00   0.50    3.75    --  107.75  77.00 150.00  166
 67  \w     86.00 122.00   0.50    3.75    --  107.75  79.00 161.02   72
 68  \w     72.00 106.00   0.50    3.75    --  107.75 -15.00  60.00   68
 69  \w     91.00 118.00   0.50    3.75    --  107.75 -61.00  60.00   54
 70  \w    111.00 136.00   0.50    3.75    --  107.75 -90.00 120.71   50
 71  \w     87.00 116.00   0.50    3.75    --  107.75-125.00  60.00   58
 72  \w     76.00 107.00   0.50    3.75    --  107.75 -94.00  90.00   62
 73  \w     79.00 115.00   0.50    3.75    --  107.75-125.00 120.00   72
 74  \w     60.00 122.00   0.50    3.75    --  107.75 -61.00 150.00  124
 75  \w     62.00 113.00   0.50    3.75    --  107.75-125.00  90.00  102
 76  \w     47.00  85.00   0.50    3.75    --  107.75 -61.00  60.00   76
 77  \w     41.00  72.00   0.50    3.75    --  107.75 -94.00  90.00   62
 78  \w     39.00  67.00   0.50    3.75    --  107.75 -37.00 104.00   56
 79  \w     42.00  67.00   0.50    3.75    --  107.75 -30.00 150.00   50
 80  \w     36.00  96.00   0.50    3.75    --  107.75 -90.00 120.71  120
 81  \w     41.00  69.00   0.50    3.75    --  107.75 -30.00  30.00   56
 82  \w     34.00  66.00   0.50    3.75    --  107.75 -15.00  60.00   64
 83  \w     38.00  92.00   0.50    3.75    --  107.75 -77.00   0.00  108
 84  \w     76.00 113.00   0.50    3.75    --  107.75-115.00 -58.28   74
 85  \w     83.00 113.00   0.50    3.75    --  107.75-125.00-120.00   60
 86  \w    104.00 130.00   0.50    3.75    --  107.75 -90.00 -99.84   52
 87  \w     90.00 116.00   0.50    3.75    --  107.75-125.00 -90.00   52
 88  \w     64.00 116.00   0.50    3.75    --  107.75-125.00-180.00  104
 89  \w     62.00  88.00   0.50    3.75    --  107.75 -77.00-180.00   52
 90  \w     45.00  74.00   0.50    3.75    --  107.75 -45.00-180.00   58
 91  \w     76.00 107.00   0.50    3.75    --  107.75 -15.00-120.00   62
 92  \w     51.00  77.00   0.50    3.75    --  107.75 -90.00 -99.84   52
 93  \w     47.00  84.00   0.50    3.75    --  107.75-125.00 -90.00   74
 94  \w     56.00 111.00   0.50    3.75    --  107.75-106.00-177.81  110
 95  \w     41.00  70.00   0.50    0.94    --   48.42 -99.00 -60.00   58
 96  \w     31.00  95.00   0.50    0.94    --   48.42-125.00 -30.00  128
 97  \w     34.00  95.00   0.50    0.94    --   48.42-125.00-120.00  122
 98  \w     36.00  65.00   0.50    3.75    --  107.75 -30.00-120.00   58
 99  \w     34.00  62.00   0.50    3.75    --  107.75 -15.00-120.00   56
100  \w     40.00 109.00   0.50    3.75    --  107.75 -61.00 -90.00  138
101  \w     40.00  71.00   0.50    3.75    --  107.75 -94.00 -30.00   62
102  \w     44.00  98.00   0.50    3.75    --  107.75 -94.00   0.00  108
103  \w     41.00 107.00   0.50    3.75    --  107.75 -94.00 -60.00  132
104  \w     38.00  63.00   0.50    3.75    --  107.75-125.00-120.00   50
105  \w     36.00 103.00   0.50    3.75    --  107.75 -94.00 -90.00  134
106  \w     36.00  82.00   0.50    3.75    --  107.75-125.00  60.00   92
107  \w     40.00 110.00   0.50    0.94    --   48.42  37.00-180.00  140
108  \w     58.00  84.00   0.50    0.94    --   48.42  77.00-150.00   52
109  \w     27.00  59.00   0.50    0.94    --   48.42  77.00-180.00   64
110  \w     27.00  52.00   0.50    0.94    --   48.42  77.00-150.00   50
111  \w     27.00  56.00   0.50    0.94    --   48.42  77.00-120.00   58
112  \w     85.00 111.00   0.50    3.75    --  107.75  80.00-162.22   52
113  \w    -22.00   4.00   0.50    0.94    --  -48.42  37.00 -99.00   52
114  \w    -60.00 -34.00   0.50    0.94    --  -48.42 -57.00   0.00   52
115  \w    -52.00 -27.00   0.50    0.94    --  -48.42 -77.00 -30.00   50
116  \w    -84.00 -37.00   0.50    0.94    --  -48.42 -37.00 -30.00   94
117  \w    -67.00 -42.00   0.50    3.75    --  -86.25  37.00 -99.00   50
118  \w    -87.00 -35.00   0.50    0.94    --  -48.42 -57.00-120.00  104
119  \w    -87.00 -62.00   0.50    3.75    --  -86.25 -82.00 -87.84   50
120  \w    -87.00 -62.00   0.50    3.75    --  -86.25 -83.00 -58.26   50
121  \w    -92.00 -67.00   0.50    3.75    --  -86.25 -70.00-111.25   50
122  \w    -97.00 -65.00   0.50    3.75    --  -86.25 -76.00 -53.05   64
123  \w    -95.00 -62.00   0.50    3.75    --  -86.25 -82.00 -33.49   66
124  \w    -89.00 -64.00   0.50    3.75    --  -86.25 -78.00   7.64   50
125  \w    -90.00 -64.00   0.50    3.75    --  -86.25 -77.00  60.00   52
126  \w    -89.00 -63.00   0.50    3.75    --  -86.25 -81.00 115.51   52
127  \w    -90.00 -64.00   0.50    3.75    --  -86.25 -77.00 150.00   52
128  \w    -94.00 -68.00   0.50    3.75    --  -86.25 -70.00 127.83   52
129  \w    -96.00 -63.00   0.50    3.75    --  -86.25 -80.00 101.66   66
130  \w    -90.00 -64.00   0.50    3.75    --  -86.25 -78.00  52.05   52
131  \w    -93.00 -67.00   0.50    3.75    --  -86.25 -70.00   8.68   52
132  \w    -87.00 -62.00   0.50    3.75    --  -86.25 -82.00 -11.11   50
133  \w    -91.00 -65.00   0.50    3.75    --  -86.25 -77.00   0.00   52
134  \w    -90.00 -64.00   0.50    3.75    --  -86.25 -77.00  30.00   52
135  \w    -88.00 -62.00   0.50    3.75    --  -86.25 -82.00  86.11   52
136  \w    -90.00 -64.00   0.50    3.75    --  -86.25 -77.00 120.00   52
137  \w    -95.00 -68.00   0.50    3.75    --  -86.25 -67.00 145.26   54
138  \w    -98.00 -67.00   0.50    3.75    --  -86.25 -74.00 168.48   62
139  \w    -71.00 -41.00   0.50    0.94    --  -48.42 -37.00 104.00   60
140  \w    -54.00 -28.00   0.50    0.94    --  -48.42 -77.00  60.00   52
141  \w    -94.00 -65.00   0.50    3.75    --  -86.25 -76.00  85.97   58
142  \w   -119.00 -80.00   0.50    0.94    --  -48.42 -37.00 104.00   78
143  \w   -131.00-104.00   0.50    3.75    --  -86.25 -37.00 104.00   54
144  \w   -154.00-128.00   0.50    3.75    --  -86.25 -82.00 -11.11   52
145  \w   -103.00 -69.00   0.50    3.75    --  -86.25 -69.00 -17.33   68
146  \w    -96.00 -64.00   0.50    3.75    --  -86.25 -77.00 -30.00   64
147  \w   -108.00 -66.00   0.50    3.75    --  -86.25 -73.00 -87.41   84
148  \w    -87.00 -62.00   0.50    3.75    --  -86.25 -83.00-144.90   50
149  \w    -92.00 -66.00   0.50    3.75    --  -86.25 -75.00-129.07   52
150  \w    -91.00 -66.00   0.50    3.75    --  -86.25 -73.00-123.78   50
151  \w    -90.00 -64.00   0.50    3.75    --  -86.25 -78.00-134.99   52
152  \w    -90.00 -64.00   0.50    3.75    --  -86.25 -77.00-180.00   52
153  \w    -98.00 -66.00   0.50    3.75    --  -86.25 -73.00-173.83   64
154  \w   -127.00-101.00   0.50    3.75    --  -86.25 -76.00 -53.05   52
155  \w   -118.00 -86.00   0.50    0.94    --  -48.42 -37.00 -30.00   64
156  \w   -152.00-126.00   0.50    3.75    --  -86.25 -82.00 -87.84   52
157  \w   -156.00-129.00   0.50    3.75    --  -86.25 -76.00 -53.05   54
158  \w   -158.00-129.00   0.50    3.75    --  -86.25 -83.00 -58.26   58
159  \w   -156.00-126.00   0.50    3.75    --  -86.25 -73.00-123.78   60
;
_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      -0.0038305000
_diffrn_orient_matrix_UB_12      -0.0495719000
_diffrn_orient_matrix_UB_13      -0.1212628000
_diffrn_orient_matrix_UB_21      0.1197340000
_diffrn_orient_matrix_UB_22      -0.0021643000
_diffrn_orient_matrix_UB_23      0.0050069000
_diffrn_orient_matrix_UB_31      -0.0006877000
_diffrn_orient_matrix_UB_32      -0.0928619000
_diffrn_orient_matrix_UB_33      0.0646673000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            86822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         3.438
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (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 colourless'
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038
_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     257
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0546P)^2^+0.6674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4114
_reflns_number_total             4317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b06744_si_002.cif
_cod_data_source_block           rjcs2_abs
_cod_database_code               4132810
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C23H30N4O
_chemical_oxdiff_usercomment     'Crystallized from chloroform.'
_reflns_odcompleteness_completeness 98.82
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.769