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_7158383
_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         'C25 H22 N4 O S2'
_chemical_formula_sum            'C25 H22 N4 O S2'
_chemical_formula_weight         458.58
_chemical_name_common
1,5-bis(thiophenyl)-2,4-bis(methylbenzyl)-carbohydrazide
_chemical_name_systematic
1,5-bis(thiophenyl)-2,4-bis(methylbenzyl)-carbohydrazide
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_audit_update_record
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.812(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9089(3)
_cell_length_b                   11.6130(2)
_cell_length_c                   10.5619(2)
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.9210
_cell_measurement_theta_min      4.4390
_cell_volume                     2319.04(7)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.958
_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     23.00 114.00   0.50    0.05    --   45.57  77.00  90.00  182
  2  \w     23.00 118.00   0.50    0.05    --   45.57  77.00 -30.00  190
  3  \w     34.00 119.00   0.50    0.05    --   45.57  38.00 -90.00  170
  4  \w     31.00 118.00   0.50    0.05    --   45.57  55.00-153.00  174
  5  \w     30.00  71.00   0.50    0.16    --  102.29 -61.00 -60.00   82
  6  \w     30.00  71.00   0.50    0.16    --  102.29 -61.00-120.00   82
  7  \w     30.00  71.00   0.50    0.16    --  102.29 -61.00-150.00   82
  8  \w     30.00  71.00   0.50    0.16    --  102.29 -61.00 -30.00   82
  9  \w     30.00  63.00   0.50    0.16    --  102.29 -55.00  63.00   66
 10  \w     30.00  71.00   0.50    0.16    --  102.29 -61.00  90.00   82
 11  \w     79.00 174.00   0.50    0.16    --  102.29  78.00  60.00  190
 12  \w     86.00 174.00   0.50    0.16    --  102.29  61.00   0.00  176
 13  \w     88.00 174.00   0.50    0.16    --  102.29  55.00-153.00  172
 14  \w    -26.00  30.00   0.50    0.05    --  -45.57  19.00 -30.00  112
 15  \w    -71.00 -30.00   0.50    0.16    -- -102.29  61.00  60.00   82
 16  \w    -71.00 -30.00   0.50    0.16    -- -102.29  61.00   0.00   82
 17  \w    -26.00  30.00   0.50    0.05    --  -45.57  19.00  60.00  112
 18  \w    -71.00 -30.00   0.50    0.16    -- -102.29  61.00 -30.00   82
 19  \w    -71.00 -30.00   0.50    0.16    -- -102.29  61.00-120.00   82
 20  \w    -63.00 -30.00   0.50    0.16    -- -102.29  55.00-153.00   66
 21  \w   -174.00 -83.00   0.50    0.16    -- -102.29 -93.00-162.00  182
 22  \w   -174.00 -90.00   0.50    0.16    -- -102.29 -45.00   0.00  168
 23  \w   -176.00 -89.00   0.50    0.16    -- -102.29 -15.00 120.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0687489000
_diffrn_orient_matrix_UB_12      -0.0614416000
_diffrn_orient_matrix_UB_13      -0.0414248000
_diffrn_orient_matrix_UB_21      0.0023469000
_diffrn_orient_matrix_UB_22      0.0621000000
_diffrn_orient_matrix_UB_23      -0.1286845000
_diffrn_orient_matrix_UB_31      0.0437225000
_diffrn_orient_matrix_UB_32      -0.0998798000
_diffrn_orient_matrix_UB_33      -0.0545843000
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10618
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.449
_diffrn_reflns_theta_min         4.468
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79650
_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    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.181
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0577P)^2^+1.3245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2154
_reflns_number_total             2302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01946e2.cif
_cod_data_source_block           12b
_cod_depositor_comments
'Adding full bibliography for 7158376--7158384.cif.'
_cod_original_cell_volume        2319.05(7)
_cod_database_code               7158383
_chemical_oxdiff_formula         'C25 H22 N4 O S2'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C1(H1), C11(H11), C3(H3), C12(H12), C2(H2), C13(H13), C4(H4)
;
_shelx_res_checksum              56720
_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.815