<i>N</i>-2,6-Di(isopropyl)phenyl-2-azaphenalenyl radical cations.
Inoue, Takeru; Matsuura, Yuuka; Horii, Koki; Konishi, Akihito; Nishida, Jun-Ichi; Yasuda, Makoto; Kawase, Takeshi; Chemical communications (Cambridge, England) 60 (2024) 1735–1738; doi:10.1039/d3cc05968e

data_7132650
_publ_section_title
;
 <i>N</i>-2,6-Di(isopropyl)phenyl-2-azaphenalenyl radical cations.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1735
_journal_page_last               1738
_journal_paper_doi               10.1039/d3cc05968e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'F6 P, C32 H41 N'
_chemical_formula_sum            'C32 H41 F6 N P'
_chemical_formula_weight         584.63
_chemical_melting_point          438.5(5)
_chemical_name_common            'N-aryl-2-azaphenalenyl radical cation'
_chemical_name_systematic
'N-di(isopropyl)phenyl-5,8-di-tert-butyl-2-azaphenalenyl radical cation'
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
_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             2021-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                112.089(2)
_cell_angle_beta                 90.039(2)
_cell_angle_gamma                102.919(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0504(2)
_cell_length_b                   11.3069(2)
_cell_length_c                   13.5760(3)
_cell_measurement_reflns_used    12454
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.8220
_cell_measurement_theta_min      4.3950
_cell_volume                     1525.21(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -82.00  -1.00   0.50    0.28    --  -42.80 103.00  67.00  162
  2  \w    -64.00 -34.00   0.50    1.12    -- -106.00  77.00 150.00   60
  3  \w    -75.00 -41.00   0.50    1.12    -- -106.00  77.00 120.00   68
  4  \w    -89.00 -48.00   0.50    1.12    -- -106.00  67.00 108.00   82
  5  \w    -92.00 -66.00   0.50    1.12    -- -106.00 125.00 150.00   52
  6  \w   -102.00 -75.00   0.50    1.12    -- -106.00 103.00  67.00   54
  7  \w   -116.00 -55.00   0.50    1.12    -- -106.00 125.00  90.00  122
  8  \w   -125.00 -99.00   0.50    1.12    -- -106.00  67.00 108.00   52
  9  \w   -124.00 -98.00   0.50    1.12    -- -106.00  83.00 150.95   52
 10  \w   -117.00 -40.00   0.50    1.12    -- -106.00 125.00 120.00  154
 11  \w   -111.00 -85.00   0.50    1.12    -- -106.00 125.00 -30.00   52
 12  \w    -88.00 -34.00   0.50    1.12    -- -106.00 138.00 -64.78  108
 13  \w    -57.00 -32.00   0.50    1.12    -- -106.00 125.00-120.00   50
 14  \w    -59.00 -33.00   0.50    1.12    -- -106.00 125.00-180.00   52
 15  \w    -75.00 -50.00   0.50    1.12    -- -106.00  64.00-137.32   50
 16  \w    -59.00 -34.00   0.50    1.12    -- -106.00  25.00 -95.55   50
 17  \w    -88.00 -62.00   0.50    1.12    -- -106.00  25.00 -95.55   52
 18  \w    -84.00 -36.00   0.50    1.12    -- -106.00  19.00-180.00   96
 19  \w   -114.00 -16.00   0.50    0.28    --  -42.80 -77.00 -30.00  196
 20  \w    -89.00 -39.00   0.50    1.12    -- -106.00  19.00   0.00  100
 21  \w   -100.00 -75.00   0.50    1.12    -- -106.00 -19.00 -30.00   50
 22  \w   -114.00 -30.00   0.50    1.12    -- -106.00  37.00 -60.00  168
 23  \w   -110.00 -84.00   0.50    1.12    -- -106.00 125.00-180.00   52
 24  \w   -111.00 -66.00   0.50    1.12    -- -106.00 125.00-120.00   90
 25  \w   -121.00 -93.00   0.50    1.12    -- -106.00  64.00-137.32   56
 26  \w   -121.00 -96.00   0.50    1.12    -- -106.00  72.00-177.79   50
 27  \w   -123.00 -98.00   0.50    1.12    -- -106.00  79.00-133.03   50
 28  \w   -116.00 -82.00   0.50    1.12    -- -106.00 125.00-150.00   68
 29  \w   -117.00 -91.00   0.50    1.12    -- -106.00 125.00 -90.00   52
 30  \w   -126.00 -95.00   0.50    1.12    -- -106.00 138.00 -64.78   62
 31  \w   -126.00-101.00   0.50    1.12    -- -106.00 138.00  11.48   50
 32  \w   -114.00 -54.00   0.50    1.12    -- -106.00 125.00   0.00  120
 33  \w   -128.00 -72.00   0.50    1.12    -- -106.00 141.00 146.71  112
 34  \w   -128.00-102.00   0.50    1.12    -- -106.00  77.00 120.00   52
 35  \w   -126.00 -81.00   0.50    1.12    -- -106.00  87.00  18.42   90
 36  \w   -128.00 -33.00   0.50    1.12    -- -106.00  57.00  30.00  190
 37  \w   -110.00 -84.00   0.50    1.12    -- -106.00 -19.00  90.00   52
 38  \w   -126.00 -92.00   0.50    1.12    -- -106.00 -37.00  90.00   68
 39  \w   -109.00 -84.00   0.50    1.12    -- -106.00 -99.00  30.00   50
 40  \w   -118.00 -70.00   0.50    1.12    -- -106.00-125.00   0.00   96
 41  \w   -108.00 -72.00   0.50    0.28    --  -42.80-125.00  30.00   72
 42  \w   -111.00 -86.00   0.50    1.12    -- -106.00 -37.00 -60.00   50
 43  \w   -128.00 -96.00   0.50    1.12    -- -106.00 -99.00   0.00   64
 44  \w   -144.00-119.00   0.50    1.12    -- -106.00 -37.00 -60.00   50
 45  \w   -138.00-110.00   0.50    1.12    -- -106.00 -99.00 -90.00   56
 46  \w   -132.00-106.00   0.50    1.12    -- -106.00-109.00-125.66   52
 47  \w   -127.00 -76.00   0.50    1.12    -- -106.00-125.00-120.00  102
 48  \w   -164.00-139.00   0.50    1.12    -- -106.00 -99.00 -90.00   50
 49  \w   -160.00-110.00   0.50    1.12    -- -106.00-125.00-150.00  100
 50  \w   -169.00-138.00   0.50    1.12    -- -106.00-103.00 -34.00   62
 51  \w   -158.00-126.00   0.50    1.12    -- -106.00-125.00   0.00   64
 52  \w   -171.00 -87.00   0.50    1.12    -- -106.00 -57.00  60.00  168
 53  \w   -118.00 -71.00   0.50    1.12    -- -106.00-125.00 120.00   94
 54  \w   -170.00-145.00   0.50    1.12    -- -106.00 -19.00 -30.00   50
 55  \w   -171.00-120.00   0.50    1.12    -- -106.00 -99.00  30.00  102
 56  \w   -173.00-146.00   0.50    1.12    -- -106.00 -19.00  90.00   54
 57  \w   -174.00-142.00   0.50    1.12    -- -106.00 -37.00  90.00   64
 58  \w   -175.00 -83.00   0.50    1.12    -- -106.00 -99.00 120.00  184
 59  \w   -115.00 -89.00   0.50    1.12    -- -106.00  57.00   0.00   52
 60  \w   -134.00-109.00   0.50    1.12    -- -106.00  19.00-180.00   50
 61  \w     -6.00  53.00   0.50    0.28    --   42.80-103.00 -34.00  118
 62  \w     32.00  57.00   0.50    1.12    --   76.50-103.00 -34.00   50
 63  \w     10.00  95.00   0.50    0.28    --   42.80-125.00-180.00  170
 64  \w    -33.00  65.00   0.50    0.28    --   42.80 -37.00-150.00  196
 65  \w     80.00 119.00   0.50    1.12    --   76.50  57.00-150.00   78
 66  \w     71.00  96.00   0.50    0.28    --   42.80 125.00 -60.00   50
 67  \w     92.00 117.00   0.50    1.12    --   76.50 103.00  67.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0426384000
_diffrn_orient_matrix_UB_12      -0.0493081000
_diffrn_orient_matrix_UB_13      -0.1133296000
_diffrn_orient_matrix_UB_21      -0.0800781000
_diffrn_orient_matrix_UB_22      0.0765598000
_diffrn_orient_matrix_UB_23      -0.0333126000
_diffrn_orient_matrix_UB_31      0.1113984000
_diffrn_orient_matrix_UB_32      0.1211140000
_diffrn_orient_matrix_UB_33      0.0343197000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.118
_diffrn_reflns_theta_min         3.529
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic intense brown'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             618
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane-Hexane'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0740
_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^)+(0.1096P)^2^+1.6112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5471
_reflns_number_total             6168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05968e2.cif
_cod_data_source_block           radicalcation
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '438-439' was changed to
'438.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7132650.cif.
;
_cod_database_code               7132650
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H20 P F6 N'
_chemical_oxdiff_usercomment     DCM/hexane
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.844
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C30(H30), C27(H27)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C1(H1), C7(H7), C9(H9), C5(H5), C25(H25), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C20(H20A,H20B,
 H20C), C31(H31A,H31B,H31C), C29(H29A,H29B,H29C), C18(H18A,H18B,H18C), C15(H15A,
 H15B,H15C), C14(H14A,H14B,H14C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              70062
_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 1.932
_oxdiff_exptl_absorpt_empirical_full_min 0.602