#------------------------------------------------------------------------------
#$Date: 2017-05-05 06:23:28 +0300 (Fri, 05 May 2017) $
#$Revision: 196220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/00/7120093.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7120093
loop_
_publ_author_name
'Kuznetsov, Iliya E.'
'Susarova, Diana K.'
'Frolova, Lyubov A.'
'Peregudov, Alexander S.'
'Shestakov, Alexander F.'
'Troyanov, Sergey I.'
'Stevenson, Keith J.'
'Troshin, Pavel A.'
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0750P)²+10.0000P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N -0.2824(9) 0.1816(4) 0.3470(4) 0.0362(14) Uani 1 1 d . . .
N2 N 0.2098(9) 0.5527(5) 0.0614(3) 0.0332(13) Uani 1 1 d . . .
N3 N 0.7683(9) 0.0358(5) 0.0742(3) 0.0363(14) Uani 1 1 d . . .
N4 N 0.4819(9) -0.0941(5) 0.1775(3) 0.0351(14) Uani 1 1 d . . .
N5 N -0.0653(8) 0.3170(4) 0.2233(3) 0.0284(13) Uani 1 1 d . . .
N6 N 0.3973(8) 0.3238(4) 0.0746(3) 0.0270(12) Uani 1 1 d . . .
N7 N 0.2176(8) 0.2387(4) 0.1652(3) 0.0238(11) Uani 1 1 d . . .
N8 N 0.6687(8) 0.2565(4) 0.0154(3) 0.0286(12) Uani 1 1 d . . .
H8A H 0.6819 0.3110 -0.0076 0.034 Uiso 1 1 calc R U .
H8B H 0.7535 0.2084 0.0064 0.034 Uiso 1 1 calc R U .
O1 O -0.0012(8) 0.8500(4) 0.0334(3) 0.0388(13) Uani 1 1 d . . .
H1 H -0.047(17) 0.908(9) 0.048(7) 0.09(4) Uiso 1 1 d . . .
C1 C 0.1438(9) 0.0825(5) 0.2537(4) 0.0264(14) Uani 1 1 d . . .
C2 C 0.0192(9) 0.1622(5) 0.2579(4) 0.0266(14) Uani 1 1 d . . .
C3 C 0.0534(9) 0.2416(5) 0.2134(4) 0.0259(14) Uani 1 1 d . . .
C4 C 0.3423(9) 0.1564(5) 0.1559(4) 0.0252(14) Uani 1 1 d . . .
C5 C 0.2980(9) 0.0782(5) 0.2007(3) 0.0247(13) Uani 1 1 d . . .
C6 C -0.0361(9) 0.3991(5) 0.1867(3) 0.0254(14) Uani 1 1 d . . .
C7 C 0.1232(9) 0.4029(5) 0.1365(4) 0.0239(13) Uani 1 1 d . . .
C8 C 0.2530(9) 0.3202(5) 0.1231(4) 0.0253(14) Uani 1 1 d . . .
C9 C 0.5213(9) 0.2469(5) 0.0637(4) 0.0265(14) Uani 1 1 d . . .
C10 C 0.4977(9) 0.1627(5) 0.1039(4) 0.0257(14) Uani 1 1 d . . .
C11 C -0.1462(10) 0.1729(5) 0.3081(4) 0.0268(14) Uani 1 1 d . . .
C12 C 0.1705(9) 0.4862(5) 0.0943(4) 0.0269(14) Uani 1 1 d . . .
C13 C 0.6419(9) 0.0886(5) 0.0902(4) 0.0266(14) Uani 1 1 d . . .
C14 C 0.4046(10) -0.0155(5) 0.1872(4) 0.0277(14) Uani 1 1 d . . .
C15 C 0.1141(10) 0.0076(5) 0.3066(4) 0.0267(15) Uani 1 1 d . . .
C16 C 0.2723(10) 0.0061(5) 0.3594(4) 0.0297(15) Uani 1 1 d . . .
H16 H 0.4032 0.0492 0.3593 0.036 Uiso 1 1 calc R U .
C17 C 0.2391(11) -0.0578(5) 0.4118(4) 0.0321(15) Uani 1 1 d . . .
H17 H 0.3481 -0.0564 0.4486 0.039 Uiso 1 1 calc R U .
C18 C 0.0520(11) -0.1245(5) 0.4130(4) 0.0321(16) Uani 1 1 d . . .
C19 C -0.1060(11) -0.1228(5) 0.3593(4) 0.0320(16) Uani 1 1 d . . .
H19 H -0.2358 -0.1673 0.3588 0.038 Uiso 1 1 calc R U .
C20 C -0.0781(10) -0.0580(5) 0.3068(4) 0.0305(15) Uani 1 1 d . . .
H20 H -0.1881 -0.0578 0.2711 0.037 Uiso 1 1 calc R U .
C21 C 0.0180(13) -0.1944(6) 0.4704(4) 0.0432(19) Uani 1 1 d . . .
H21A H -0.0481 -0.1536 0.5176 0.065 Uiso 1 1 calc R U .
H21B H 0.1485 -0.2066 0.4893 0.065 Uiso 1 1 calc R U .
H21C H -0.0683 -0.2687 0.4416 0.065 Uiso 1 1 calc R U .
C22 C -0.1805(9) 0.4786(5) 0.2083(4) 0.0261(14) Uani 1 1 d . . .
C23 C -0.2786(10) 0.4844(5) 0.2786(4) 0.0339(16) Uani 1 1 d . . .
H23 H -0.2477 0.4400 0.3118 0.041 Uiso 1 1 calc R U .
C24 C -0.4213(11) 0.5538(6) 0.3017(4) 0.0373(17) Uani 1 1 d . . .
H24 H -0.4866 0.5565 0.3503 0.045 Uiso 1 1 calc R U .
C25 C -0.4695(10) 0.6195(5) 0.2541(4) 0.0312(16) Uani 1 1 d . . .
C26 C -0.3707(10) 0.6140(5) 0.1834(4) 0.0310(15) Uani 1 1 d . . .
H26 H -0.4015 0.6585 0.1503 0.037 Uiso 1 1 calc R U .
C27 C -0.2280(10) 0.5446(5) 0.1605(4) 0.0305(15) Uani 1 1 d . . .
H27 H -0.1621 0.5419 0.1120 0.037 Uiso 1 1 calc R U .
C28 C -0.6295(11) 0.6928(5) 0.2784(4) 0.0380(17) Uani 1 1 d . . .
H28A H -0.6185 0.7484 0.2484 0.057 Uiso 1 1 calc R U .
H28B H -0.6094 0.7336 0.3375 0.057 Uiso 1 1 calc R U .
H28C H -0.7641 0.6437 0.2652 0.057 Uiso 1 1 calc R U .
C29 C 0.5583(14) 0.4117(6) 0.4711(5) 0.045(2) Uani 1 1 d . . .
C30 C 0.2097(16) 0.4261(7) 0.4284(5) 0.065(3) Uani 1 1 d . . .
C31 C 0.386(2) 0.4768(11) 0.4765(8) 0.041(4) Uani 0.5 1 d . . P
C32 C 0.389(2) 0.3632(11) 0.4267(8) 0.040(3) Uani 0.5 1 d . . P
C33 C 0.727(3) 0.4574(13) 0.5136(11) 0.052(5) Uani 0.5 1 d . . P
C34 C -0.0820(11) 0.7918(6) 0.0887(4) 0.0359(16) Uani 1 1 d . . .
H34A H 0.0224 0.8019 0.1325 0.054 Uiso 1 1 calc R U .
H34B H -0.1257 0.7100 0.0589 0.054 Uiso 1 1 calc R U .
H34C H -0.1980 0.8238 0.1126 0.054 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 N5 C6 121.4(5) . .
C8 N6 C9 119.2(5) . .
C3 N7 C4 122.4(5) . .
C3 N7 C8 117.6(5) . .
C4 N7 C8 120.0(4) . .
C2 C1 C5 118.0(5) . .
C2 C1 C15 119.9(5) . .
C5 C1 C15 122.0(6) . .
C1 C2 C3 121.6(5) . .
C1 C2 C11 123.2(5) . .
C3 C2 C11 115.2(6) . .
N5 C3 N7 123.9(5) . .
N5 C3 C2 117.8(5) . .
N7 C3 C2 118.2(5) . .
C10 C4 N7 115.8(5) . .
C10 C4 C5 127.6(6) . .
N7 C4 C5 116.6(5) . .
C1 C5 C4 123.0(6) . .
C1 C5 C14 117.4(5) . .
C4 C5 C14 119.4(5) . .
N5 C6 C7 119.2(5) . .
N5 C6 C22 113.2(5) . .
C7 C6 C22 127.6(5) . .
C6 C7 C8 120.7(5) . .
C6 C7 C12 124.5(5) . .
C8 C7 C12 114.8(5) . .
N6 C8 N7 123.2(5) . .
N6 C8 C7 119.7(5) . .
N7 C8 C7 117.1(5) . .
N8 C9 N6 116.5(5) . .
N8 C9 C10 122.0(6) . .
N6 C9 C10 121.5(5) . .
C4 C10 C9 120.4(5) . .
C4 C10 C13 122.9(5) . .
C9 C10 C13 116.7(5) . .
N1 C11 C2 178.3(7) . .
N2 C12 C7 179.3(8) . .
N3 C13 C10 172.5(6) . .
N4 C14 C5 176.5(6) . .
C16 C15 C20 119.2(6) . .
C16 C15 C1 120.4(5) . .
C20 C15 C1 120.3(6) . .
C17 C16 C15 119.8(6) . .
C16 C17 C18 122.4(7) . .
C17 C18 C19 117.3(6) . .
C17 C18 C21 121.9(7) . .
C19 C18 C21 120.9(6) . .
C20 C19 C18 121.6(6) . .
C19 C20 C15 119.7(7) . .
C23 C22 C27 118.5(6) . .
C23 C22 C6 117.5(6) . .
C27 C22 C6 123.9(5) . .
C22 C23 C24 121.1(6) . .
C23 C24 C25 120.5(6) . .
C26 C25 C24 118.4(6) . .
C26 C25 C28 121.4(6) . .
C24 C25 C28 120.2(5) . .
C27 C26 C25 121.0(6) . .
C26 C27 C22 120.4(5) . .
C33 C29 C32 178.5(12) . .
C33 C29 C31 53.1(10) . 2_666
C32 C29 C31 128.3(12) . 2_666
C33 C29 C31 121.5(10) . .
C32 C29 C31 60.0(9) . .
C31 C29 C31 68.5(11) 2_666 .
C31 C30 C33 49.6(10) . 2_666
C31 C30 C32 57.9(9) . .
C33 C30 C32 107.5(11) 2_666 .
C33 C31 C30 69.7(14) 2_666 .
C33 C31 C29 58.8(11) 2_666 2_666
C30 C31 C29 128.5(14) . 2_666
C33 C31 C32 137.0(18) 2_666 .
C30 C31 C32 67.3(10) . .
C29 C31 C32 163.8(16) 2_666 .
C33 C31 C29 170.1(15) 2_666 .
C30 C31 C29 119.8(10) . .
C29 C31 C29 111.6(11) 2_666 .
C32 C31 C29 52.5(9) . .
C33 C31 C31 118.2(16) 2_666 2_666
C30 C31 C31 171.2(16) . 2_666
C29 C31 C31 59.4(8) 2_666 2_666
C32 C31 C31 104.6(16) . 2_666
C29 C31 C31 52.1(9) . 2_666
C29 C32 C31 67.6(10) . .
C29 C32 C30 122.3(11) . .
C31 C32 C30 54.8(9) . .
C31 C33 C29 68.2(13) 2_666 .
C31 C33 C30 60.7(10) 2_666 2_666
C29 C33 C30 128.8(13) . 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.150(7) .
N2 C12 1.141(8) .
N3 C13 1.152(8) .
N4 C14 1.157(8) .
N5 C3 1.311(8) .
N5 C6 1.348(7) .
N6 C8 1.300(7) .
N6 C9 1.351(8) .
N7 C3 1.398(7) .
N7 C4 1.409(8) .
N7 C8 1.413(7) .
N8 C9 1.324(7) .
O1 C34 1.430(7) .
C1 C2 1.394(9) .
C1 C5 1.397(8) .
C1 C15 1.487(8) .
C2 C3 1.420(8) .
C2 C11 1.427(8) .
C4 C10 1.402(7) .
C4 C5 1.418(8) .
C5 C14 1.437(8) .
C6 C7 1.398(7) .
C6 C22 1.480(8) .
C7 C8 1.433(8) .
C7 C12 1.439(8) .
C9 C10 1.416(8) .
C10 C13 1.427(8) .
C15 C16 1.387(10) .
C15 C20 1.408(8) .
C16 C17 1.377(9) .
C17 C18 1.389(9) .
C18 C19 1.396(10) .
C18 C21 1.505(8) .
C19 C20 1.382(9) .
C22 C23 1.383(8) .
C22 C27 1.396(9) .
C23 C24 1.387(9) .
C24 C25 1.393(10) .
C25 C26 1.390(8) .
C25 C28 1.515(9) .
C26 C27 1.387(9) .
C29 C33 1.28(2) .
C29 C32 1.297(18) .
C29 C31 1.386(14) 2_666
C29 C31 1.512(18) .
C30 C31 1.366(18) .
C30 C33 1.470(18) 2_666
C30 C32 1.543(18) .
C31 C33 1.19(2) 2_666
C31 C29 1.386(14) 2_666
C31 C32 1.416(18) .
C31 C31 1.63(3) 2_666
C33 C31 1.19(2) 2_666
C33 C30 1.470(18) 2_666
