# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_P21c
_audit_block_doi                 10.5517/ccdc.csd.cc21hl27
_database_code_depnum_ccdc_archive 'CCDC 1891808'
loop_
_audit_author_name
_audit_author_address
Nap-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.	2020-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Nap-D
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 N6'
_chemical_formula_weight         540.61

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1579(5)
_cell_length_b                   21.3968(10)
_cell_length_c                   6.9520(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.940(3)
_cell_angle_gamma                90
_cell_volume                     1316.19(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3197
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      68.17

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHTOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7101
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.132
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2370
_reflns_number_gt                1784
_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)+(0.0661P)²+0.3119P] 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       0.0033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2370
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.28770(19) 0.48022(8) 0.4152(3) 0.0358(4) Uani 1 1 d . . . . .
C1 C 0.2256(2) 0.40250(10) 0.6361(3) 0.0361(5) Uani 1 1 d . . . . .
C2 C 0.1290(2) 0.44480(10) 0.6934(3) 0.0403(5) Uani 1 1 d . . . . .
H2 H 0.111238 0.484603 0.631171 0.048 Uiso 1 1 calc R U . . .
N2 N 0.38933(19) 0.37737(8) 0.4318(3) 0.0360(4) Uani 1 1 d . . . . .
C3 C 0.0586(3) 0.42888(11) 0.8410(4) 0.0472(6) Uani 1 1 d . . . . .
H3 H -0.007147 0.457945 0.879184 0.057 Uiso 1 1 calc R U . . .
N3 N 0.47061(19) 0.39534(8) 0.2992(3) 0.0350(4) Uani 1 1 d . . . . .
C4 C 0.0832(3) 0.37124(12) 0.9329(4) 0.0495(6) Uani 1 1 d . . . . .
H4 H 0.035111 0.360665 1.034300 0.059 Uiso 1 1 calc R U . . .
C5 C 0.1792(3) 0.32879(11) 0.8756(4) 0.0472(6) Uani 1 1 d . . . . .
H5 H 0.196646 0.288973 0.937750 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2489(2) 0.34453(10) 0.7284(3) 0.0415(5) Uani 1 1 d . . . . .
H6 H 0.313872 0.315209 0.689623 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3038(2) 0.42079(9) 0.4807(3) 0.0342(4) Uani 1 1 d . . . . .
C8 C 0.5900(2) 0.35162(9) 0.3000(3) 0.0338(5) Uani 1 1 d . . . . .
C9 C 0.5542(2) 0.29060(9) 0.2430(3) 0.0376(5) Uani 1 1 d . . . . .
H9 H 0.451638 0.277606 0.202525 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6699(3) 0.24833(10) 0.2456(3) 0.0454(6) Uani 1 1 d . . . . .
H10 H 0.646798 0.206128 0.207092 0.054 Uiso 1 1 calc R U . . .
C11 C 0.8182(3) 0.26772(11) 0.3041(3) 0.0485(6) Uani 1 1 d . . . . .
H11 H 0.896799 0.238885 0.302842 0.058 Uiso 1 1 calc R U . . .
C12 C 0.8541(2) 0.32861(11) 0.3646(3) 0.0434(5) Uani 1 1 d . . . . .
H12 H 0.956827 0.341288 0.406909 0.052 Uiso 1 1 calc R U . . .
C13 C 0.7394(2) 0.37110(10) 0.3632(3) 0.0380(5) Uani 1 1 d . . . . .
H13 H 0.762792 0.413017 0.404908 0.046 Uiso 1 1 calc R U . . .
C14 C 0.4485(2) 0.45193(9) 0.1995(3) 0.0319(4) Uani 1 1 d . . . . .
C15 C 0.3579(2) 0.49519(9) 0.2746(3) 0.0332(4) Uani 1 1 d . . . . .
C16 C 0.5080(2) 0.46818(9) 0.0362(3) 0.0327(4) Uani 1 1 d . . . . .
C17 C 0.5845(2) 0.42483(9) -0.0586(3) 0.0353(5) Uani 1 1 d . . . . .
H17 H 0.588980 0.382154 -0.019754 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6509(2) 0.44260(9) -0.2022(3) 0.0347(5) Uani 1 1 d . . . . .
H18 H 0.705266 0.412465 -0.256412 0.042 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 C15 1.340(2) . ?
N1 C7 1.346(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.393(3) . ?
C1 C7 1.495(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
N2 C7 1.315(3) . ?
N2 N3 1.380(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
N3 C14 1.384(2) . ?
N3 C8 1.438(2) . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.379(3) . ?
C8 C13 1.389(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C16 1.423(3) . ?
C14 C15 1.428(3) . ?
C15 C18 1.418(3) 3_665 ?
C16 C17 1.422(3) . ?
C16 C16 1.446(4) 3_665 ?
C17 C18 1.351(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C15 N1 C7 116.16(17) . . ?
C6 C1 C2 118.83(18) . . ?
C6 C1 C7 121.53(18) . . ?
C2 C1 C7 119.63(19) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C7 N2 N3 115.82(16) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
N2 N3 C14 122.93(16) . . ?
N2 N3 C8 110.91(15) . . ?
C14 N3 C8 125.74(15) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N2 C7 N1 126.94(18) . . ?
N2 C7 C1 115.49(18) . . ?
N1 C7 C1 117.42(17) . . ?
C9 C8 C13 121.12(18) . . ?
C9 C8 N3 119.38(19) . . ?
C13 C8 N3 119.48(18) . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 119.2(2) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
N3 C14 C16 125.21(17) . . ?
N3 C14 C15 114.05(17) . . ?
C16 C14 C15 120.74(18) . . ?
N1 C15 C18 119.28(17) . 3_665 ?
N1 C15 C14 123.02(18) . . ?
C18 C15 C14 117.63(17) 3_665 . ?
C17 C16 C14 123.07(18) . . ?
C17 C16 C16 118.1(2) . 3_665 ?
C14 C16 C16 118.9(2) . 3_665 ?
C18 C17 C16 121.88(19) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C15 122.10(18) . 3_665 ?
C17 C18 H18 119.0 . . ?
C15 C18 H18 119.0 3_665 . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.045


_exptl_crystal_preparation       'Magnetic properties'
