Isolation of 1,4,5,8-tetraazanaphthalene radicals.
Deshapriya, Saroshan; Demir, Selvan; Chemical communications (Cambridge, England) 61 (2025) 12301–12304; doi:10.1039/d5cc03096j

data_7134849
_publ_section_title
;
 Isolation of 1,4,5,8-tetraazanaphthalene radicals.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12301
_journal_page_last               12304
_journal_paper_doi               10.1039/d5cc03096j
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety
'2(C18 H36 K N2 O6), 2(C6 H4 N4), C4 H9 O2, 0.5(C4 H10 O2)'
_chemical_formula_sum            'C54 H94 K2 N12 O15'
_chemical_formula_weight         1229.61
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-27
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.22 svn.r631f81ec for OlexSys, GUI svn.r7248)
;
_audit_update_record
;
2025-05-30 deposited with the CCDC.	2025-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                93.4050(10)
_cell_angle_beta                 108.7290(10)
_cell_angle_gamma                111.4740(10)
_cell_formula_units_Z            2
_cell_length_a                   13.11390(10)
_cell_length_b                   14.30790(10)
_cell_length_c                   19.88320(10)
_cell_measurement_reflns_used    32648
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.4810
_cell_measurement_theta_min      2.3530
_cell_volume                     3220.98(5)
_computing_cell_refinement       'CrysAlisPro 1.171.44.107a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 44.107a 64-bit (release 22-04-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.107a (Rigaku OD, 2025)'
_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      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -49.00   0.00   0.50    0.25    --  -47.66  43.00-103.00   98
  2  \w   -115.00 -40.00   0.50    0.25    --  -47.66 -43.00 104.00  150
  3  \w     38.00 119.00   0.50    0.25    --   47.66  43.00-103.00  162
  4  \w    -12.00  47.00   0.50    0.25    --   47.66 -43.00 104.00  118
  5  \w   -164.00-128.00   0.50    1.02    --  -91.75 -43.00 104.00   72
  6  \w    -49.00 -24.00   0.50    1.02    --  -91.75  43.00-103.00   50
  7  \w    102.00 145.00   0.50    1.02    --  113.25  43.00-103.00   86
  8  \w    -70.00   6.00   0.50    0.25    --  -47.66  77.00 -90.00  152
  9  \w    -13.00  25.00   0.50    0.25    --  -47.66  19.00  30.00   76
 10  \w    -31.00  26.00   0.50    0.25    --  -47.66  19.00-180.00  114
 11  \w    -54.00 -20.00   0.50    0.25    --  -47.66 125.00 -30.00   68
 12  \w     -9.00  16.00   0.50    0.25    --   47.66 -19.00 -30.00   50
 13  \w     61.00  93.00   0.50    0.25    --   47.66-125.00 -60.00   64
 14  \w    -47.00 -20.00   0.50    1.02    --  -91.75  45.00  60.00   54
 15  \w    -50.00 -21.00   0.50    1.02    --  -91.75  45.00  90.00   58
 16  \w   -163.00-136.00   0.50    1.02    --  -91.75-125.00-120.00   54
 17  \w     42.00 104.00   0.50    1.02    --  113.25 -94.00-120.00  124
 18  \w     45.00 102.00   0.50    1.02    --  113.25 -94.00 -90.00  114
 19  \w     43.00  69.00   0.50    1.02    --  113.25 -61.00 120.00   52
 20  \w     46.00  74.00   0.50    1.02    --  113.25 -77.00-180.00   56
 21  \w     57.00 104.00   0.50    1.02    --  113.25 -94.00 -60.00   94
 22  \w     53.00 104.00   0.50    1.02    --  113.25 -94.00  90.00  102
 23  \w     43.00  68.00   0.50    1.02    --  113.25 -61.00-120.00   50
 24  \w    101.00 178.00   0.50    1.02    --  113.25  45.00 -60.00  154
 25  \w    105.00 175.00   0.50    1.02    --  113.25  30.00  90.00  140
 26  \w    100.00 177.00   0.50    1.02    --  113.25  15.00 -30.00  154
 27  \w    108.00 153.00   0.50    1.02    --  113.25  45.00-150.00   90
 28  \w     43.00  74.00   0.50    1.02    --  113.25 -94.00 -30.00   62
 29  \w     79.00 104.00   0.50    1.02    --  113.25 -94.00 -30.00   50
 30  \w     43.00  77.00   0.50    1.02    --  113.25 -77.00 120.00   68
 31  \w     76.00 102.00   0.50    1.02    --  113.25 -94.00 150.00   52
 32  \w     42.00  67.00   0.50    1.02    --  113.25 -61.00   0.00   50
 33  \w     50.00 104.00   0.50    1.02    --  113.25 -99.00  52.41  108
 34  \w     43.00  69.00   0.50    1.02    --  113.25 -61.00  60.00   52
 35  \w    102.00 159.00   0.50    1.02    --  113.25  15.00 150.00  114
 36  \w     79.00 104.00   0.50    1.02    --  113.25 -94.00  60.00   50
 37  \w    150.00 177.00   0.50    1.02    --  113.25  30.00  30.00   54
 38  \w     79.00 104.00   0.50    1.02    --  113.25 -94.00   0.00   50
 39  \w     48.00  78.00   0.50    1.02    --  113.25-125.00  90.00   60
 40  \w     42.00  97.00   0.50    1.02    --  113.25 -77.00 -30.00  110
 41  \w    102.00 140.00   0.50    1.02    --  113.25  30.00  30.00   76
 42  \w     83.00 108.00   0.50    1.02    --  113.25-125.00  90.00   50
 43  \w     42.00  68.00   0.50    1.02    --  113.25 -94.00-180.00   52
 44  \w     79.00 104.00   0.50    1.02    --  113.25 -94.00-180.00   50
 45  \w    125.00 150.00   0.50    1.02    --  113.25  77.00-120.00   50
 46  \w     65.00 103.00   0.50    1.02    --  113.25 -94.00-150.00   76
 47  \w    103.00 173.00   0.50    1.02    --  113.25  45.00-180.00  140
 48  \w    116.00 175.00   0.50    1.02    --  113.25  77.00 150.00  118
 49  \w     98.00 130.00   0.50    1.02    --  113.25 125.00-180.00   64
 50  \w    136.00 169.00   0.50    1.02    --  113.25 125.00-180.00   66
 51  \w     51.00 103.00   0.50    1.02    --  113.25 -94.00 120.00  104
 52  \w     75.00 100.00   0.50    1.02    --  113.25 -77.00 -60.00   50
 53  \w     47.00  99.00   0.50    1.02    --  113.25 -77.00  90.00  104
 54  \w     72.00  97.00   0.50    1.02    --  113.25 -77.00 150.00   50
 55  \w     43.00  68.00   0.50    1.02    --  113.25 -94.00   0.00   50
 56  \w    102.00 155.00   0.50    1.02    --  113.25  15.00   0.00  106
 57  \w     44.00  69.00   0.50    1.02    --  113.25 -61.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0720281000
_diffrn_orient_matrix_UB_12      -0.0527134000
_diffrn_orient_matrix_UB_13      0.0452101000
_diffrn_orient_matrix_UB_21      0.0459980000
_diffrn_orient_matrix_UB_22      -0.0849094000
_diffrn_orient_matrix_UB_23      0.0006565000
_diffrn_orient_matrix_UB_31      0.1055715000
_diffrn_orient_matrix_UB_32      0.0629400000
_diffrn_orient_matrix_UB_33      0.0702146000
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52049
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.070
_diffrn_reflns_theta_min         2.395
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.107a (Rigaku Oxford Diffraction, 2025)
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 dark blue'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       needle
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.934
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1092
_refine_ls_number_reflns         13790
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+1.9054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12530
_reflns_number_total             13790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03096j2.cif
_cod_data_source_block           '[K(crypt-222)]TAN'
_cod_depositor_comments
'Adding full bibliography for 7134847--7134849.cif.'
_cod_original_cell_volume        3220.97(5)
_cod_database_code               7134849
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         KN6O6C20H40
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.671
_diffrn_oxdiff_digest_hkl
;
438ab2601cec58e4c82dba9fe1959e17a8a49a
;
_diffrn_oxdiff_digest_od_ed
;

;
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 O2S, O1S, C4S, C3S, C2S, C1S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2. Others
 Fixed Sof: O2S(0.5) O1S(0.5) C4S(0.5) H4SA(0.5) H4SB(0.5) H4SC(0.5) C3S(0.5)
 H3SA(0.5) H3SB(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5)
 H1SC(0.5)
3.a Riding coordinates:
 C8S(H8SB,H8SA), C028(H02A,H02B), C5S(H5SA,H5SB), C9S(H9SA,H9SB,H9SC),
 C4S(H4SA,H4SB,H4SC), C3S(H3SA,H3SB), C2S(H2SA,H2SB), C1S(H1SA,H1SB,H1SC)
3.b Free rotating group:
 O2S(O1S,C4S)
;
_shelx_res_checksum              57919
_shelx_hkl_checksum              81314
_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 1.619
_oxdiff_exptl_absorpt_empirical_full_min 0.641