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_7158376
_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         'C8 H11 N5 O3 S'
_chemical_formula_sum            'C8 H11 N5 O3 S'
_chemical_formula_weight         257.28
_chemical_name_common
1,5-di(methylbenzene)-3-(4-nitro-thiophenyl-oxoverdazyl
_chemical_name_systematic
1,5-di(methylbenzene)-3-(4-nitro-thiophenyl-oxoverdazyl
_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
_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                 105.809(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.73880(10)
_cell_length_b                   8.73770(10)
_cell_length_c                   15.3935(3)
_cell_measurement_reflns_used    8557
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.0630
_cell_measurement_theta_min      5.8520
_cell_volume                     1130.94(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -81.00  14.00   0.50    1.00    --  -46.07 102.00  92.00  190
  2  \w    -14.00  81.00   0.50    1.00    --   46.07-102.00 -10.00  190
  3  \w   -174.00 -85.00   0.50    5.00    -- -102.29-102.00 -10.00  178
  4  \w   -106.00 -30.00   0.50    5.00    -- -102.29 102.00  92.00  152
  5  \w     30.00 106.00   0.50    5.00    --  102.29-102.00 -10.00  152
  6  \w     85.00 174.00   0.50    5.00    --  102.29 102.00  92.00  178
  7  \w    -26.00  29.00   0.50    1.00    --  -46.07  19.00  30.00  110
  8  \w   -119.00 -73.00   0.50    1.00    --  -46.07-125.00  60.00   92
  9  \w     74.00 119.00   0.50    1.00    --   46.07 125.00  60.00   90
 10  \w     74.00 119.00   0.50    1.00    --   46.07 125.00  90.00   90
 11  \w     31.00 119.00   0.50    1.00    --   46.07  57.00-180.00  176
 12  \w     74.00 119.00   0.50    1.00    --   46.07 125.00   0.00   90
 13  \w   -174.00 -84.00   0.50    5.00    -- -102.29 -65.00   8.87  180
 14  \w    -71.00 -30.00   0.50    5.00    -- -102.29  61.00  60.00   82
 15  \w    -71.00 -30.00   0.50    5.00    -- -102.29  61.00-120.00   82
 16  \w   -121.00 -30.00   0.50    5.00    -- -102.29 138.00-102.67  182
 17  \w   -174.00 -86.00   0.50    5.00    -- -102.29 -62.00 -66.20  176
 18  \w    -71.00 -30.00   0.50    5.00    -- -102.29  61.00 120.00   82
 19  \w   -105.00 -30.00   0.50    5.00    -- -102.29  77.00-120.00  150
 20  \w   -174.00 -90.00   0.50    5.00    -- -102.29 -46.00 -98.30  168
 21  \w    -71.00 -30.00   0.50    5.00    -- -102.29  61.00 -60.00   82
 22  \w   -174.00 -80.00   0.50    5.00    -- -102.29 -77.00-120.00  188
 23  \w   -174.00 -85.00   0.50    5.00    -- -102.29 -64.00  29.91  178
 24  \w     30.00 111.00   0.50    5.00    --  102.29-125.00-150.00  162
 25  \w     30.00 105.00   0.50    5.00    --  102.29 -77.00 -30.00  150
 26  \w     30.00 111.00   0.50    5.00    --  102.29-125.00-120.00  162
 27  \w     30.00  71.00   0.50    5.00    --  102.29 -61.00  30.00   82
 28  \w     90.00 174.00   0.50    5.00    --  102.29  45.00-180.00  168
 29  \w     30.00  71.00   0.50    5.00    --  102.29 -61.00   0.00   82
 30  \w     30.00 105.00   0.50    5.00    --  102.29 -94.00 150.00  150
 31  \w     24.00 119.00   0.50    1.00    --   46.07  77.00 -60.00  190
 32  \w     24.00 119.00   0.50    1.00    --   46.07  77.00  60.00  190
 33  \w     31.00 119.00   0.50    1.00    --   46.07  57.00  30.00  176
 34  \w     24.00 119.00   0.50    1.00    --   46.07  77.00  90.00  190
 35  \w     24.00 119.00   0.50    1.00    --   46.07  77.00-180.00  190
 36  \w     24.00 119.00   0.50    1.00    --   46.07  77.00-120.00  190
 37  \w   -176.00-110.00   0.50    5.00    -- -102.29 -30.00  90.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20676
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.258
_diffrn_reflns_theta_min         5.261
_exptl_absorpt_coefficient_mu    2.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.033
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0414P)^2^+0.8363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2078
_reflns_number_total             2293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01946e2.cif
_cod_data_source_block           13c
_cod_depositor_comments
'Adding full bibliography for 7158376--7158384.cif.'
_cod_database_code               7158376
_chemical_oxdiff_formula         'C8 H11 N5 O3 S'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'
_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 Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              40081
_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
;