# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_sd6d
_database_code_depnum_ccdc_archive 'CCDC 1522029'
_audit_update_record             
;
2016-12-11 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-amino-2,8-bis-p-tolyl-1,4,9b-triazaphenalene-3,6,7,9-tetracarbonitrile
_chemical_name_common            'Para-tolyl substituted 1,4,9b-triazaphenalene'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32.50 H24 N8 O'
_chemical_formula_weight         542.60

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7285(2)
_cell_length_b                   12.4807(4)
_cell_length_c                   17.2061(8)
_cell_angle_alpha                107.9080(13)
_cell_angle_beta                 91.5310(15)
_cell_angle_gamma                99.840(2)
_cell_volume                     1349.83(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10000
_cell_measurement_theta_min      4
_cell_measurement_theta_max      32

_exptl_crystal_description       needle
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             566
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.905
_diffrn_radiation_type           synchrotron
_diffrn_source                   'BL 14.2 PSF, BESSY, Berlin, Germany'
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6940
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.223
_diffrn_reflns_theta_max         36.417
_diffrn_reflns_theta_full        32.555
_diffrn_measured_fraction_theta_max 0.577
_diffrn_measured_fraction_theta_full 0.713
_diffrn_reflns_Laue_measured_fraction_max 0.577
_diffrn_reflns_Laue_measured_fraction_full 0.713
_diffrn_reflns_point_group_measured_fraction_max 0.577
_diffrn_reflns_point_group_measured_fraction_full 0.713
_reflns_number_total             3686
_reflns_number_gt                3360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       HKL2000
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    XS
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
A solvated toluene molecule is disordered around an inversion center.
;
_vrf_PLAT029_sd6d                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.713 Note  
RESPONSE: The use of a square detector and the existence of some shaded 
detector areas resulted in the reduced data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.099(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3686
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.1070
_refine_ls_wR_factor_ref         0.2806
_refine_ls_wR_factor_gt          0.2788
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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 ?

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
_geom_angle_publ_flag
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 ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.090


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: PhMe/MeOH mixture'
