Unprecedented thermal condensation of tetracyanocyclopropanes to triazaphenalenes: a facile route for the design of novel materials for electronic applications.
Kuznetsov, Iliya E.; Susarova, Diana K.; Frolova, Lyubov A.; Peregudov, Alexander S.; Shestakov, Alexander F.; Troyanov, Sergey I.; Stevenson, Keith J.; Troshin, Pavel A.; Chemical communications (Cambridge, England) 53 (2017) 4830–4833; doi:10.1039/c6cc10179h

data_7120093
_publ_section_title
;
 Unprecedented thermal condensation of tetracyanocyclopropanes to
 triazaphenalenes: a facile route for the design of novel materials for
 electronic applications.
;
_journal_issue                   35
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4830
_journal_page_last               4833
_journal_paper_doi               10.1039/c6cc10179h
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C32.5 H24 N8 O'
_chemical_formula_weight         542.60
_chemical_name_common
'Para-tolyl substituted 1,4,9b-triazaphenalene'
_chemical_name_systematic
5-amino-2,8-bis-p-tolyl-1,4,9b-triazaphenalene-3,6,7,9-tetracarbonitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-11 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                107.9080(13)
_cell_angle_beta                 91.5310(15)
_cell_angle_gamma                99.840(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7285(2)
_cell_length_b                   12.4807(4)
_cell_length_c                   17.2061(8)
_cell_measurement_reflns_used    10000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      4
_cell_volume                     1349.83(9)
_computing_cell_refinement       HKL2000
_computing_data_collection       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    XS
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.713
_diffrn_measured_fraction_theta_max 0.577
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.905
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.713
_diffrn_reflns_Laue_measured_fraction_max 0.577
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6940
_diffrn_reflns_point_group_measured_fraction_full 0.713
_diffrn_reflns_point_group_measured_fraction_max 0.577
_diffrn_reflns_theta_full        32.555
_diffrn_reflns_theta_max         36.417
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'BL 14.2 PSF, BESSY, Berlin, Germany'
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       needle
_exptl_crystal_F_000             566
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: PhMe/MeOH mixture'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.099(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.1070
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2788
_refine_ls_wR_factor_ref         0.2806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3360
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc10179h2.cif
_cod_data_source_block           sd6d
_cod_original_formula_sum        'C32.50 H24 N8 O'
_cod_database_code               7120093
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              27422