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_7158378
_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 O3'
_chemical_formula_sum            'C19 H22 N4 O3'
_chemical_formula_weight         354.40
_chemical_name_common
1,5-bis(3-methoxybenzyl)-2,4-dimethyl-carbohydrazide
_chemical_name_systematic
1,5-bis(3-methoxybenzyl)-2,4-dimethyl-carbohydrazide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.97880(10)
_cell_length_b                   14.73690(10)
_cell_length_c                   22.0879(2)
_cell_measurement_reflns_used    18553
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3570
_cell_measurement_theta_min      3.9780
_cell_volume                     3573.68(5)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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     32.00 118.00   0.50    0.06    --   46.32  57.00   0.00  172
  2  \w     90.00 174.00   0.50    0.45    --  102.29  45.00-120.00  168
  3  \w    -26.00  43.00   0.50    0.06    --   46.32 -38.00-180.00  138
  4  \w     30.00 105.00   0.50    0.45    --  102.29 -77.00 -60.00  150
  5  \w     30.00  71.00   0.50    0.45    --  102.29 -61.00 150.00   82
  6  \w     13.00  94.00   0.50    0.06    --   46.32-125.00 -90.00  162
  7  \w     30.00 111.00   0.50    0.45    --  102.29-125.00 150.00  162
  8  \w     30.00 108.00   0.50    0.45    --  102.29-113.00  77.00  156
  9  \w   -118.00 -24.00   0.50    0.06    --  -46.32 -77.00 150.00  188
 10  \w   -120.00 -32.00   0.50    0.06    --  -46.32 -14.00-133.00  176
 11  \w   -118.00 -79.00   0.50    0.06    --  -46.32 -57.00-150.00   78
 12  \w   -174.00 -80.00   0.50    0.45    -- -102.29 -77.00-180.00  188
 13  \w   -176.00 -88.00   0.50    0.45    -- -102.29 -14.00-133.00  176
 14  \w    -71.00 -30.00   0.50    0.45    -- -102.29  61.00 -90.00   82
 15  \w    -26.00  29.00   0.50    0.06    --  -46.32  19.00-180.00  110
 16  \w    -71.00 -30.00   0.50    0.45    -- -102.29  61.00-180.00   82
 17  \w   -116.00 -30.00   0.50    0.45    -- -102.29 131.00-111.00  172
 18  \w   -108.00 -30.00   0.50    0.45    -- -102.29 113.00 169.00  156
 19  \w   -176.00 -90.00   0.50    0.45    -- -102.29 -30.00  90.00  172
;
_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      0.1170889000
_diffrn_orient_matrix_UB_12      -0.0129511000
_diffrn_orient_matrix_UB_13      0.0374068000
_diffrn_orient_matrix_UB_21      0.0771114000
_diffrn_orient_matrix_UB_22      0.0147593000
_diffrn_orient_matrix_UB_23      -0.0574385000
_diffrn_orient_matrix_UB_31      0.0035586000
_diffrn_orient_matrix_UB_32      0.1027041000
_diffrn_orient_matrix_UB_33      0.0130014000
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.558
_diffrn_reflns_theta_min         4.003
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0404P)^2^+1.0484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3296
_reflns_number_total             3642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01946e2.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 7158376--7158384.cif.'
_cod_database_code               7158378
_chemical_oxdiff_formula         'C19 H22 N4 O3'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.871
_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:
 C18(H18), C12(H12), C8(H8), C7(H7), C3(H3), C14(H14), C5(H5), C4(H4),
 C16(H16), C15(H15)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              94204
_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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.896