Enhanced synthesis of oxo-verdazyl radicals bearing sterically-and electronically-diverse C3-substituents.
Fuller, Rebecca O.; Taylor, Madeleine R.; Duggin, Margot; Bissember, Alex C.; Canty, Allan J.; Judd, Martyna M.; Cox, Nicholas; Moggach, Stephen A.; Turner, Gemma F.; Organic & biomolecular chemistry 19 (2021) 10120–10138; doi:10.1039/d1ob01946e

data_7158377
_publ_section_title
;
 Enhanced synthesis of oxo-verdazyl radicals bearing sterically-and
 electronically-diverse C3-substituents.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10120
_journal_page_last               10138
_journal_paper_doi               10.1039/d1ob01946e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H22 N4 O'
_chemical_formula_sum            'C19 H22 N4 O'
_chemical_formula_weight         322.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                102.5530(10)
_cell_angle_beta                 92.8410(10)
_cell_angle_gamma                111.3200(10)
_cell_formula_units_Z            2
_cell_length_a                   7.58380(10)
_cell_length_b                   9.81170(10)
_cell_length_c                   12.89680(10)
_cell_measurement_reflns_used    23822
_cell_measurement_temperature    101(1)
_cell_measurement_theta_max      75.3330
_cell_measurement_theta_min      3.5340
_cell_volume                     863.837(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_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     24.00 119.00   0.50    0.05    --   46.07  77.00 150.00  190
  2  \w     24.00 119.00   0.50    0.05    --   46.07  77.00  90.00  190
  3  \w     29.00 119.00   0.50    0.05    --   46.07  64.00  79.00  180
  4  \w     24.00 119.00   0.50    0.05    --   46.07  77.00  60.00  190
  5  \w     28.00 122.00   0.50    0.05    --   50.00  76.00-119.87  188
  6  \w     24.00 119.00   0.50    0.05    --   46.07  77.00-180.00  190
  7  \w     34.00 119.00   0.50    0.05    --   46.07  38.00-180.00  170
  8  \w     34.00 122.00   0.50    0.05    --   46.07  19.00-180.00  176
  9  \w     87.00 177.00   0.50    0.25    --  103.87  64.00  79.00  180
 10  \w     31.00 126.00   0.50    0.05    --   54.00  77.00 158.43  190
 11  \w     35.00 131.00   0.50    0.05    --   58.00  77.00  71.98  192
 12  \w     63.00 152.00   0.50    0.25    --   86.00  77.00  55.40  178
 13  \w     32.00 126.00   0.50    0.05    --   54.00  76.00 -34.48  188
 14  \w     74.00 100.00   0.50    0.05    --   66.00  77.00-104.74   52
 15  \w     44.00  70.00   0.50    0.05    --   66.00  77.00-104.74   52
 16  \w     40.00  66.00   0.50    0.05    --   62.00  77.00 -72.89   52
 17  \w     32.00 126.00   0.50    0.05    --   54.00  75.00 -80.86  188
 18  \w     41.00 128.00   0.50    0.05    --   62.00  73.00-114.66  174
 19  \w     32.00 126.00   0.50    0.05    --   54.00  76.00  16.09  188
 20  \w     42.00  68.00   0.50    0.05    --   62.00  75.00  25.41   52
 21  \w     43.00  68.00   0.50    0.05    --   62.00  76.00  90.21   50
 22  \w     14.00  43.00   0.50    0.05    --   42.00  88.00-117.61   58
 23  \w      5.00  43.00   0.50    0.05    --   34.00  90.00 -74.57   76
 24  \w    -16.00  22.00   0.50    0.05    --   18.00 100.00 -88.79   76
 25  \w    -21.00  14.00   0.50    0.05    --   14.00 102.00 -27.09   70
 26  \w     31.00  76.00   0.50    0.25    --  103.87 -64.00 -56.00   90
 27  \w     36.00  71.00   0.50    0.25    --  103.87 -61.00   0.00   70
 28  \w    -25.00  61.00   0.50    0.05    --   46.07 -57.00  90.00  172
 29  \w    -25.00  64.00   0.50    0.05    --   46.07 -64.00 -56.00  178
 30  \w     31.00  69.00   0.50    0.25    --  103.87 -61.00 -90.00   76
 31  \w     32.00  60.00   0.50    0.25    --  103.87 -94.00-120.00   56
 32  \w     73.00 111.00   0.50    0.25    --  103.87-125.00-150.00   76
 33  \w     38.00  67.00   0.50    0.25    --  103.87-125.00 -30.00   58
 34  \w     72.00 112.00   0.50    0.25    --  103.87-125.00 -30.00   80
 35  \w     85.00 112.00   0.50    0.25    --  103.87-125.00   0.00   54
 36  \w     33.00  97.00   0.50    0.25    --  103.87 -94.00 120.00  128
 37  \w     52.00 112.00   0.50    0.25    --  103.87-125.00  90.00  120
 38  \w     75.00 105.00   0.50    0.25    --  103.87 -94.00 150.00   60
 39  \w     46.00  72.00   0.50    0.25    --  103.87 -94.00 150.00   52
 40  \w     64.00  93.00   0.50    0.25    --  103.87 -94.00-120.00   58
 41  \w     38.00  69.00   0.50    0.25    --  103.87 -94.00-150.00   62
 42  \w     72.00 104.00   0.50    0.25    --  103.87 -94.00-150.00   64
 43  \w   -108.00 -41.00   0.50    0.25    -- -103.87 125.00  60.00  134
 44  \w   -107.00 -79.00   0.50    0.25    -- -103.87 125.00  30.00   56
 45  \w    -76.00 -50.00   0.50    0.25    -- -103.87 125.00  30.00   52
 46  \w    -87.00 -34.00   0.50    0.25    -- -103.87 125.00 -60.00  106
 47  \w    -64.00 -33.00   0.50    0.25    -- -103.87  61.00 -60.00   62
 48  \w    -70.00 -32.00   0.50    0.25    -- -103.87  61.00-150.00   76
 49  \w    -63.00  27.00   0.50    0.05    --  -46.07  64.00  79.00  180
 50  \w    -76.00 -31.00   0.50    0.25    -- -103.87  64.00  79.00   90
 51  \w   -174.00-143.00   0.50    0.25    -- -103.87 -45.00  30.00   62
 52  \w   -166.00 -80.00   0.50    0.25    -- -103.87 -79.00  11.04  172
 53  \w   -176.00 -80.00   0.50    0.25    -- -103.87 -79.00-100.74  192
 54  \w   -175.00-121.00   0.50    0.25    -- -103.87 -77.00-140.45  108
 55  \w   -113.00 -83.00   0.50    0.25    -- -103.87 -77.00-140.45   60
 56  \w   -126.00 -76.00   0.50    0.25    --  -98.00 -77.00 -81.99  100
 57  \w   -159.00-132.00   0.50    0.25    --  -98.00 -77.00 -81.99   54
 58  \w   -161.00-117.00   0.50    0.25    --  -94.00 -76.00  24.21   88
 59  \w   -100.00 -71.00   0.50    0.25    --  -94.00 -76.00  24.21   58
 60  \w   -166.00 -71.00   0.50    0.25    --  -94.00 -76.00 -13.58  190
 61  \w   -174.00-131.00   0.50    0.25    -- -103.87 -77.00 120.00   86
 62  \w   -118.00 -81.00   0.50    0.25    -- -103.87 -77.00 120.00   74
 63  \w    -77.00 -51.00   0.50    0.05    --  -74.00 -76.00 149.33   52
 64  \w    -91.00 -64.00   0.50    0.25    --  -86.00 -75.00 138.32   54
 65  \w    -83.00 -52.00   0.50    0.05    --  -74.00 -75.00 103.98   62
 66  \w    -86.00 -51.00   0.50    0.05    --  -74.00 -76.00  18.54   70
 67  \w   -145.00-119.00   0.50    0.05    --  -74.00 -75.00 103.98   52
 68  \w   -138.00 -97.00   0.50    0.05    --  -74.00 -76.00  18.54   82
 69  \w    -82.00 -52.00   0.50    0.05    --  -74.00 -75.00  67.85   60
 70  \w   -115.00 -68.00   0.50    0.25    --  -90.00 -74.00 -75.26   94
 71  \w    -79.00 -54.00   0.50    0.05    --  -74.00 -74.00 -99.20   50
 72  \w   -155.00 -65.00   0.50    0.25    --  -86.00 -74.00-115.29  180
 73  \w   -153.00 -84.00   0.50    0.25    -- -103.87 -75.00-164.92  138
 74  \w    -91.00 -65.00   0.50    0.25    --  -86.00 -75.00-144.03   52
 75  \w    -78.00 -53.00   0.50    0.05    --  -74.00 -73.00 -68.75   50
 76  \w    -93.00 -65.00   0.50    0.25    --  -86.00 -73.00  27.28   56
 77  \w    -86.00 -61.00   0.50    0.25    --  -82.00 -72.00  83.92   50
 78  \w    -95.00 -67.00   0.50    0.25    --  -86.00 -72.00  64.45   56
 79  \w   -158.00-108.00   0.50    0.25    --  -86.00 -72.00  64.45  100
 80  \w   -150.00 -99.00   0.50    0.25    --  -82.00 -72.00 149.50  102
 81  \w    -93.00 -61.00   0.50    0.25    --  -82.00 -72.00 149.50   64
 82  \w    -82.00 -57.00   0.50    0.25    --  -78.00 -72.00 173.40   50
 83  \w   -142.00-115.00   0.50    0.25    --  -78.00 -72.00 173.40   54
 84  \w   -135.00 -42.00   0.50    0.05    --  -62.00 -70.00 168.16  186
 85  \w   -100.00 -66.00   0.50    0.25    --  -86.00 -71.00 114.06   68
 86  \w   -148.00 -85.00   0.50    0.25    -- -103.87 -68.00 152.03  126
 87  \w    -80.00 -54.00   0.50    0.05    --  -74.00 -69.00 -36.93   52
 88  \w    -79.00 -51.00   0.50    0.05    --  -70.00 -68.00 -57.76   56
 89  \w   -122.00 -80.00   0.50    0.25    --  -98.00 -70.00-146.75   84
 90  \w   -153.00-127.00   0.50    0.25    --  -98.00 -70.00-146.75   52
 91  \w    -94.00 -64.00   0.50    0.25    --  -82.00 -65.00 -66.81   60
 92  \w   -119.00 -29.00   0.50    0.05    --  -46.07 -64.00 -56.00  180
 93  \w   -109.00 -68.00   0.50    0.25    --  -86.00 -64.00 -11.71   82
 94  \w   -176.00 -86.00   0.50    0.25    -- -103.87 -64.00 -56.00  180
 95  \w   -139.00-114.00   0.50    0.25    --  -94.00 -65.00  73.31   50
 96  \w   -110.00 -76.00   0.50    0.25    --  -94.00 -65.00  73.31   68
 97  \w   -125.00 -76.00   0.50    0.25    --  -94.00 -64.00 178.84   98
 98  \w    -83.00 -57.00   0.50    0.05    --  -74.00 -66.00 115.42   52
 99  \w   -123.00 -87.00   0.50    0.25    -- -103.87 -62.00 118.44   72
100  \w    -90.00 -64.00   0.50    0.25    --  -78.00 -60.00 177.29   52
101  \w   -175.00-127.00   0.50    0.25    -- -103.87 -61.00  60.00   96
102  \w   -139.00 -93.00   0.50    0.25    -- -103.87 -45.00  30.00   92
103  \w   -110.00 -77.00   0.50    0.25    --  -94.00 -63.00 -71.29   66
104  \w   -117.00 -78.00   0.50    0.25    --  -94.00 -59.00 -65.78   78
105  \w   -152.00-120.00   0.50    0.25    --  -94.00 -59.00 -65.78   64
106  \w   -109.00 -69.00   0.50    0.25    --  -86.00 -62.00-150.27   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0291024000
_diffrn_orient_matrix_UB_12      -0.1182493000
_diffrn_orient_matrix_UB_13      -0.0902121000
_diffrn_orient_matrix_UB_21      0.1824438000
_diffrn_orient_matrix_UB_22      0.1229300000
_diffrn_orient_matrix_UB_23      -0.0186972000
_diffrn_orient_matrix_UB_31      0.1199523000
_diffrn_orient_matrix_UB_32      -0.0354389000
_diffrn_orient_matrix_UB_33      0.0824269000
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31912
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.872
_diffrn_reflns_theta_min         3.547
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0496P)^2^+0.1892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3352
_reflns_number_total             3484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01946e2.cif
_cod_data_source_block           7b
_cod_depositor_comments
'Adding full bibliography for 7158376--7158384.cif.'
_cod_original_cell_volume        863.837(17)
_cod_database_code               7158377
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H24 O N4'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00B(H00B), C00F(H00F), C00G(H00G),
 C00J(H00K), C00K(H00L), C00M(H00P), C00O(H00T)
2.b Idealised Me refined as rotating group:
 C00H(H00C,H00D,H00E), C00I(H00H,H00I,H00J), C00L(H00M,H00N,H00O), C00N(H00Q,
 H00R,H00S)
;
_shelx_res_checksum              47462
_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.874