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_7134847
_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         'C6 H4 N4'
_chemical_formula_sum            'C6 H4 N4'
_chemical_formula_weight         132.13
_chemical_name_systematic        1,4,5,8-Tetraazanaphthalene
_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   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                90
_cell_angle_beta                 94.820(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.6563(2)
_cell_length_b                   7.4254(4)
_cell_length_c                   10.3507(5)
_cell_measurement_reflns_used    1357
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.3490
_cell_measurement_theta_min      4.3070
_cell_volume                     280.02(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.977
_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    -25.00  30.00   0.50    0.05    --   47.66 -37.00  60.00  110
  2  \w    -27.00   7.00   0.50    0.05    --   47.66 -19.00 -30.00   68
  3  \w     49.00  92.00   0.50    0.11    --  113.25 -77.00 -30.00   86
  4  \w     51.00  77.00   0.50    0.11    --  113.25 -77.00  30.00   52
  5  \w     42.00  67.00   0.50    0.11    --  113.25 -61.00  60.00   50
  6  \w     42.00  67.00   0.50    0.11    --  113.25 -61.00  30.00   50
  7  \w     42.00  67.00   0.50    0.11    --  113.25 -61.00   0.00   50
  8  \w     46.00  92.00   0.50    0.11    --  113.25 -77.00-150.00   92
  9  \w     44.00  69.00   0.50    0.11    --  113.25 -77.00-180.00   50
 10  \w    -12.00  14.00   0.50    0.05    --   47.66 -19.00-180.00   52
 11  \w     44.00  95.00   0.50    0.05    --   47.66-125.00-120.00  102
 12  \w     48.00  73.00   0.50    0.11    --  113.25-125.00-150.00   50
 13  \w     78.00 105.00   0.50    0.11    --  113.25-125.00-150.00   54
 14  \w     75.00 100.00   0.50    0.11    --  113.25 -94.00-180.00   50
 15  \w     53.00  99.00   0.50    0.11    --  113.25 -94.00-120.00   92
 16  \w     43.00  72.00   0.50    0.11    --  113.25 -94.00 -60.00   58
 17  \w     77.00 102.00   0.50    0.11    --  113.25 -94.00 -60.00   50
 18  \w     74.00 104.00   0.50    0.11    --  113.25 -94.00 -30.00   60
 19  \w     46.00  72.00   0.50    0.11    --  113.25 -94.00 -30.00   52
 20  \w     63.00 103.00   0.50    0.11    --  113.25 -94.00  60.00   80
 21  \w     48.00 104.00   0.50    0.11    --  113.25 -94.00 120.00  112
 22  \w     41.00  89.00   0.50    0.05    --   47.66   0.00   0.00   96
 23  \w    119.00 147.00   0.50    0.11    --  113.25  77.00 -90.00   56
 24  \w    153.00 178.00   0.50    0.11    --  113.25  77.00 -90.00   50
 25  \w    153.00 178.00   0.50    0.11    --  113.25  61.00-120.00   50
 26  \w    114.00 146.00   0.50    0.11    --  113.25  61.00-120.00   64
 27  \w    110.00 143.00   0.50    0.11    --  113.25  45.00 -90.00   66
 28  \w    135.00 174.00   0.50    0.11    --  113.25  30.00  30.00   78
 29  \w    104.00 130.00   0.50    0.11    --  113.25  30.00  30.00   52
 30  \w    105.00 130.00   0.50    0.11    --  113.25  30.00 150.00   50
 31  \w    145.00 176.00   0.50    0.11    --  113.25  30.00 150.00   62
 32  \w    150.00 176.00   0.50    0.11    --  113.25  15.00-120.00   52
 33  \w    103.00 135.00   0.50    0.11    --  113.25  15.00-120.00   64
 34  \w    -16.00  21.00   0.50    0.05    --   47.66   0.00   0.00   74
 35  \w   -162.00-118.00   0.50    0.11    --  -91.75 -77.00-180.00   88
 36  \w   -156.00-116.00   0.50    0.11    --  -91.75 -61.00  30.00   80
 37  \w    -52.00 -22.00   0.50    0.11    --  -91.75  45.00  60.00   60
 38  \w      0.00  28.00   0.50    0.05    --  -47.66  19.00-120.00   56
 39  \w    -28.00  -2.00   0.50    0.05    --  -47.66  19.00-120.00   52
;
_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      -0.1226304000
_diffrn_orient_matrix_UB_12      -0.1770503000
_diffrn_orient_matrix_UB_13      -0.0682656000
_diffrn_orient_matrix_UB_21      0.3864200000
_diffrn_orient_matrix_UB_22      -0.0233138000
_diffrn_orient_matrix_UB_23      -0.0464755000
_diffrn_orient_matrix_UB_31      0.1198183000
_diffrn_orient_matrix_UB_32      -0.1057747000
_diffrn_orient_matrix_UB_33      0.1244287000
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2263
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.404
_diffrn_reflns_theta_min         7.350
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.493
_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 pale yellow'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       needle
_exptl_crystal_F_000             136
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0786P)^2^+0.0154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                557
_reflns_number_total             599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03096j2.cif
_cod_data_source_block           TAN
_cod_depositor_comments
'Adding full bibliography for 7134847--7134849.cif.'
_cod_database_code               7134847
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         N4C6H2
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.784
_diffrn_oxdiff_digest_hkl
;
438b0b41d904ca5423c72db3ab23ecd03ba3d0
;
_diffrn_oxdiff_digest_od_ed
;

;
_olex2_refinement_description
;
;
_shelx_res_checksum              13110
_shelx_hkl_checksum              17141
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.547