# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_S2_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21hl5b
_database_code_depnum_ccdc_archive 'CCDC 1891811'
loop_
_audit_author_name
_audit_author_address
DPh-D
;School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of
China
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        DPh-D
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H26 N6'
_chemical_formula_weight         566.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 '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                   6.0606(11)
_cell_length_b                   8.5904(19)
_cell_length_c                   13.007(3)
_cell_angle_alpha                90.724(17)
_cell_angle_beta                 93.870(16)
_cell_angle_gamma                96.893(18)
_cell_volume                     670.6(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1999
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      66.37
_cell_measurement_temperature    223.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.005
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             298

_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      223.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7165
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.406
_diffrn_reflns_theta_max         66.647
_diffrn_reflns_theta_full        66.647
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2346
_reflns_number_gt                1687
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.3004P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0037(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2346
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_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 0.6296(3) 0.2024(2) 0.58957(15) 0.0333(5) Uani 1 1 d . . . . .
C1 C 1.1532(5) 0.0188(3) 0.8401(2) 0.0434(7) Uani 1 1 d . . . . .
H1 H 1.200967 0.005018 0.909315 0.052 Uiso 1 1 calc R U . . .
N2 N 0.6898(3) 0.3292(2) 0.75586(15) 0.0339(5) Uani 1 1 d . . . . .
C2 C 1.2526(4) -0.0520(3) 0.7625(2) 0.0399(6) Uani 1 1 d . . . . .
H2 H 1.367628 -0.113695 0.778847 0.048 Uiso 1 1 calc R U . . .
C3 C 1.1826(4) -0.0319(3) 0.6611(2) 0.0392(6) Uani 1 1 d . . . . .
H3 H 1.250851 -0.079037 0.608042 0.047 Uiso 1 1 calc R U . . .
N3 N 0.5170(3) 0.4150(2) 0.73086(15) 0.0341(5) Uani 1 1 d . . . . .
C4 C 1.0118(4) 0.0577(3) 0.63734(19) 0.0360(6) Uani 1 1 d . . . . .
H4 H 0.962545 0.069186 0.568060 0.043 Uiso 1 1 calc R U . . .
C5 C 0.9123(4) 0.1309(2) 0.71461(18) 0.0306(5) Uani 1 1 d . . . . .
C6 C 0.9833(4) 0.1103(3) 0.81671(19) 0.0383(6) Uani 1 1 d . . . . .
H6 H 0.916369 0.158133 0.869945 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4591(4) 0.2871(3) 0.56681(18) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.7323(4) 0.2279(3) 0.68520(18) 0.0311(5) Uani 1 1 d . . . . .
C10 C 0.2154(4) 0.4803(3) 0.61046(18) 0.0326(5) Uani 1 1 d . . . . .
H10 H 0.175897 0.553969 0.657771 0.039 Uiso 1 1 calc R U . . .
C11 C 0.0947(4) 0.4574(3) 0.51424(18) 0.0303(5) Uani 1 1 d . . . . .
C12 C 0.1650(4) 0.3487(3) 0.44487(19) 0.0351(6) Uani 1 1 d . . . . .
H12 H 0.088621 0.332087 0.379594 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3404(4) 0.2669(3) 0.46954(19) 0.0363(6) Uani 1 1 d . . . . .
H13 H 0.382677 0.196153 0.420987 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4870(4) 0.5267(3) 0.80970(17) 0.0317(5) Uani 1 1 d . . . . .
C15 C 0.6677(4) 0.6350(3) 0.84272(18) 0.0355(6) Uani 1 1 d . . . . .
H15 H 0.801377 0.639903 0.809533 0.043 Uiso 1 1 calc R U . . .
C16 C 0.6494(4) 0.7350(3) 0.92443(19) 0.0383(6) Uani 1 1 d . . . . .
H16 H 0.770953 0.808968 0.946626 0.046 Uiso 1 1 calc R U . . .
C17 C 0.4543(4) 0.7277(3) 0.97404(19) 0.0403(6) Uani 1 1 d . . . . .
H17 H 0.444744 0.793776 1.031338 0.048 Uiso 1 1 calc R U . . .
C18 C 0.2721(4) 0.6222(3) 0.93885(19) 0.0381(6) Uani 1 1 d . . . . .
H18 H 0.137403 0.619298 0.971057 0.046 Uiso 1 1 calc R U . . .
C19 C 0.2882(4) 0.5210(3) 0.85616(19) 0.0366(6) Uani 1 1 d . . . . .
H19 H 0.165175 0.449543 0.832213 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3914(4) 0.3964(2) 0.63697(17) 0.0298(5) Uani 1 1 d . . . . .


_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 C8 1.353(3) . ?
N1 C7 1.356(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.389(3) . ?
C1 H1 0.9400 . ?
N2 C7 1.317(3) . ?
N2 N3 1.375(2) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9400 . ?
N3 C9 1.392(3) . ?
N3 C14 1.431(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.388(3) . ?
C5 C7 1.483(3) . ?
C6 H6 0.9400 . ?
C8 C13 1.411(3) . ?
C8 C9 1.416(3) . ?
C10 C9 1.384(3) . ?
C10 C11 1.406(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.412(3) . ?
C11 C11 1.463(4) 2_566 ?
C12 C13 1.366(3) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C19 1.380(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.377(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9400 . ?
C17 C18 1.390(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C8 N1 C7 115.53(19) . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C7 N2 N3 116.19(19) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N2 N3 C9 122.59(18) . . ?
N2 N3 C14 112.86(17) . . ?
C9 N3 C14 124.52(17) . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 C7 118.8(2) . . ?
C6 C5 C7 122.2(2) . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C8 C13 119.6(2) . . ?
N1 C8 C9 122.9(2) . . ?
C13 C8 C9 117.5(2) . . ?
N2 C7 N1 127.30(19) . . ?
N2 C7 C5 115.8(2) . . ?
N1 C7 C5 116.90(19) . . ?
C9 C10 C11 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 117.0(2) . . ?
C10 C11 C11 122.1(3) . 2_566 ?
C12 C11 C11 120.8(3) . 2_566 ?
C13 C12 C11 122.1(2) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C8 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C19 C14 C15 120.8(2) . . ?
C19 C14 N3 120.9(2) . . ?
C15 C14 N3 118.2(2) . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.2(2) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C10 C9 N3 123.7(2) . . ?
C10 C9 C8 120.9(2) . . ?
N3 C9 C8 115.40(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C7 N2 N3 C9 0.6(3) . . . . ?
C7 N2 N3 C14 -177.6(2) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C3 C4 C5 C7 179.0(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C7 C5 C6 C1 -179.7(2) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C7 N1 C8 C13 -179.2(2) . . . . ?
C7 N1 C8 C9 0.4(3) . . . . ?
N3 N2 C7 N1 2.2(4) . . . . ?
N3 N2 C7 C5 -177.4(2) . . . . ?
C8 N1 C7 N2 -2.7(4) . . . . ?
C8 N1 C7 C5 176.9(2) . . . . ?
C4 C5 C7 N2 -160.9(2) . . . . ?
C6 C5 C7 N2 19.5(3) . . . . ?
C4 C5 C7 N1 19.5(3) . . . . ?
C6 C5 C7 N1 -160.1(2) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C9 C10 C11 C11 178.7(3) . . . 2_566 ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C11 C12 C13 -179.6(3) 2_566 . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
N1 C8 C13 C12 178.8(2) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
N2 N3 C14 C19 -120.5(2) . . . . ?
C9 N3 C14 C19 61.4(3) . . . . ?
N2 N3 C14 C15 55.6(3) . . . . ?
C9 N3 C14 C15 -122.6(2) . . . . ?
C19 C14 C15 C16 1.6(3) . . . . ?
N3 C14 C15 C16 -174.5(2) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 -2.3(4) . . . . ?
C16 C17 C18 C19 2.1(3) . . . . ?
C15 C14 C19 C18 -1.8(3) . . . . ?
N3 C14 C19 C18 174.1(2) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C11 C10 C9 N3 179.7(2) . . . . ?
C11 C10 C9 C8 1.5(4) . . . . ?
N2 N3 C9 C10 179.3(2) . . . . ?
C14 N3 C9 C10 -2.7(4) . . . . ?
N2 N3 C9 C8 -2.4(3) . . . . ?
C14 N3 C9 C8 175.6(2) . . . . ?
N1 C8 C9 C10 -179.8(2) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
N1 C8 C9 N3 1.9(3) . . . . ?
C13 C8 C9 N3 -178.5(2) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.048


_exptl_crystal_preparation       'Magnetic properties'
