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_7158384
_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         'C15 H16 N6 O'
_chemical_formula_sum            'C15 H16 N6 O'
_chemical_formula_weight         296.34
_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             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                90
_cell_angle_beta                 98.940(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4529(3)
_cell_length_b                   10.4903(3)
_cell_length_c                   12.3136(4)
_cell_measurement_reflns_used    12819
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      74.6590
_cell_measurement_theta_min      3.8730
_cell_volume                     1461.44(7)
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_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    -28.00  26.00   0.50    0.05    --   46.20 -19.00   0.00  108
  2  \w     30.00 105.00   0.50    0.15    --  102.41 -77.00 -30.00  150
  3  \w     37.00  70.00   0.50    0.15    --  102.41 -61.00-180.00   66
  4  \w    -28.00  26.00   0.50    0.05    --   46.20 -19.00  90.00  108
  5  \w     86.00 175.00   0.50    0.15    --  102.41  61.00   0.00  178
  6  \w     49.00 118.00   0.50    0.05    --   46.20 162.00-172.00  138
  7  \w     30.00 109.00   0.50    0.15    --  102.41-117.00 -50.00  158
  8  \w     30.00 111.00   0.50    0.15    --  102.41-125.00 -90.00  162
  9  \w     36.00  75.00   0.50    0.15    --  102.41-125.00   0.00   78
 10  \w     81.00 111.00   0.50    0.15    --  102.41-125.00   0.00   60
 11  \w     32.00 118.00   0.50    0.05    --   46.20-162.00 159.00  172
 12  \w     32.00 136.00   0.50    0.15    --  102.41-162.00 159.00  208
 13  \w     36.00 105.00   0.50    0.15    --  102.41-125.00 150.00  138
 14  \w      7.00  90.00   0.50    0.05    --   46.20-117.00 -50.00  166
 15  \w   -109.00 -30.00   0.50    0.15    -- -102.41 117.00  37.00  158
 16  \w   -111.00 -30.00   0.50    0.15    -- -102.41 125.00 150.00  162
 17  \w   -123.00 -30.00   0.50    0.15    -- -102.41 141.00  41.65  186
 18  \w    -90.00  -7.00   0.50    0.05    --  -46.20 117.00  37.00  166
 19  \w   -117.00 -31.00   0.50    0.05    --  -46.20 162.00-172.00  172
 20  \w   -136.00 -31.00   0.50    0.15    -- -102.41 162.00-172.00  210
 21  \w    -71.00 -30.00   0.50    0.15    -- -102.41  61.00   0.00   82
 22  \w    -71.00 -30.00   0.50    0.15    -- -102.41  61.00  60.00   82
 23  \w   -105.00 -30.00   0.50    0.15    -- -102.41  77.00  60.00  150
 24  \w    -71.00 -30.00   0.50    0.15    -- -102.41  61.00-150.00   82
 25  \w    -71.00 -30.00   0.50    0.15    -- -102.41  61.00-120.00   82
 26  \w   -175.00 -90.00   0.50    0.15    -- -102.41 -46.00  39.76  170
 27  \w   -175.00 -84.00   0.50    0.15    -- -102.41 -65.00 176.91  182
 28  \w   -175.00 -89.00   0.50    0.15    -- -102.41 -52.00 101.86  172
 29  \w   -118.00 -23.00   0.50    0.05    --  -46.20 -77.00-120.00  190
 30  \w   -175.00 -80.00   0.50    0.15    -- -102.41 -77.00-112.23  190
 31  \w   -175.00 -88.00   0.50    0.15    -- -102.41 -54.00-139.96  174
 32  \w   -118.00 -73.00   0.50    0.05    --  -46.20-125.00   0.00   90
 33  \w   -118.00 -73.00   0.50    0.05    --  -46.20-125.00  60.00   90
 34  \w   -118.00 -49.00   0.50    0.05    --  -46.20-162.00 159.00  138
 35  \w   -156.00 -49.00   0.50    0.15    -- -102.41-162.00 159.00  214
 36  \w   -175.00 -73.00   0.50    0.15    -- -102.41-125.00  90.00  204
 37  \w   -175.00 -78.00   0.50    0.15    -- -102.41-117.00 -50.00  194
;
_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      -0.0164323000
_diffrn_orient_matrix_UB_12      0.1444264000
_diffrn_orient_matrix_UB_13      -0.0196920000
_diffrn_orient_matrix_UB_21      0.0280673000
_diffrn_orient_matrix_UB_22      -0.0166655000
_diffrn_orient_matrix_UB_23      -0.1175695000
_diffrn_orient_matrix_UB_31      -0.1324994000
_diffrn_orient_matrix_UB_32      -0.0212982000
_diffrn_orient_matrix_UB_33      -0.0419917000
_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  0.1014
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25448
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.079
_diffrn_reflns_theta_min         3.907
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.6814
_exptl_absorpt_correction_T_min  0.5382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1440 before and 0.1138 after correction.
The Ratio of minimum to maximum transmission is 0.7898.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0039(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0646
_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^)+(0.1461P)^2^+0.2626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2593
_reflns_number_total             2957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01946e2.cif
_cod_data_source_block           9b
_cod_depositor_comments
'Adding full bibliography for 7158376--7158384.cif.'
_cod_database_code               7158384
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'N4 C20 H20 O1'
_chemical_oxdiff_usercomment     'UTas sample'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C009(H009), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00O)
2.b Idealised Me refined as rotating group:
 C00J(H00B,H00C,H00J), C00L(H00L,H00M,H00N)
;
_shelx_res_checksum              20773
_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 1.766
_oxdiff_exptl_absorpt_empirical_full_min 0.655