# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 1906680'
loop_
_audit_author_name
_audit_author_address
'Zhe Peng'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-03-30 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H28 N4'
_chemical_formula_weight         564.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   26.013(6)
_cell_length_b                   12.858(2)
_cell_length_c                   10.6428(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.932(10)
_cell_angle_gamma                90
_cell_volume                     3439.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    360
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      16.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10908
_diffrn_reflns_av_unetI/netI     0.1466
_diffrn_reflns_av_R_equivalents  0.1270
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.620
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3022
_reflns_number_gt                1136
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0665P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3022
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1840
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2045
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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
C1 C 0.2486(2) 0.9581(4) 0.4893(6) 0.0926(19) Uani 1 1 d . . . . .
H1 H 0.2771 0.9917 0.4689 0.111 Uiso 1 1 calc R U . . .
C2 C 0.22483(19) 0.8774(4) 0.4085(5) 0.0760(15) Uani 1 1 d . . . . .
H2 H 0.2374 0.8574 0.3378 0.091 Uiso 1 1 calc R U . . .
C3 C 0.18224(19) 0.8280(3) 0.4360(4) 0.0632(14) Uani 1 1 d . . . . .
C4 C 0.1658(2) 0.8632(4) 0.5434(5) 0.105(2) Uani 1 1 d . . . . .
H4 H 0.1366 0.8328 0.5642 0.126 Uiso 1 1 calc R U . . .
C5 C 0.1928(3) 0.9431(4) 0.6186(5) 0.123(3) Uani 1 1 d . . . . .
H5 H 0.1815 0.9642 0.6906 0.147 Uiso 1 1 calc R U . . .
C6 C 0.15243(17) 0.7424(3) 0.3529(4) 0.0579(12) Uani 1 1 d . . . . .
C7 C 0.14921(17) 0.7370(3) 0.2216(4) 0.0698(14) Uani 1 1 d . . . . .
H7 H 0.1671 0.7856 0.1838 0.084 Uiso 1 1 calc R U . . .
C8 C 0.11943(17) 0.6596(3) 0.1458(4) 0.0635(13) Uani 1 1 d . . . . .
H8 H 0.1176 0.6568 0.0574 0.076 Uiso 1 1 calc R U . . .
C9 C 0.09257(16) 0.5871(3) 0.1990(4) 0.0501(11) Uani 1 1 d . . . . .
C10 C 0.09598(16) 0.5901(3) 0.3305(4) 0.0571(12) Uani 1 1 d . . . . .
H10 H 0.0783 0.5409 0.3681 0.069 Uiso 1 1 calc R U . . .
C11 C 0.12608(17) 0.6676(3) 0.4060(4) 0.0645(13) Uani 1 1 d . . . . .
H11 H 0.1286 0.6692 0.4948 0.077 Uiso 1 1 calc R U . . .
C12 C -0.00785(15) 0.6297(3) -0.0542(4) 0.0539(11) Uani 1 1 d . . . . .
H12 H 0.0050 0.6975 -0.0469 0.065 Uiso 1 1 calc R U . . .
C13 C 0.01554(15) 0.5429(3) 0.0184(4) 0.0501(11) Uani 1 1 d . . . . .
C14 C 0.05412(16) 0.4066(3) 0.1391(4) 0.0511(11) Uani 1 1 d . . . . .
C15 C 0.09435(17) 0.3448(3) 0.2284(4) 0.0529(12) Uani 1 1 d . . . . .
C16 C 0.08011(17) 0.2496(3) 0.2711(4) 0.0684(14) Uani 1 1 d . . . . .
H16 H 0.0446 0.2296 0.2467 0.082 Uiso 1 1 calc R U . . .
C17 C 0.1175(2) 0.1829(4) 0.3494(4) 0.0748(15) Uani 1 1 d . . . . .
H17 H 0.1067 0.1193 0.3754 0.090 Uiso 1 1 calc R U . . .
C18 C 0.1694(2) 0.2113(4) 0.3874(4) 0.0800(16) Uani 1 1 d . . . . .
H18 H 0.1943 0.1674 0.4400 0.096 Uiso 1 1 calc R U . . .
C19 C 0.18512(18) 0.3053(4) 0.3475(4) 0.0731(15) Uani 1 1 d . . . . .
H19 H 0.2207 0.3248 0.3739 0.088 Uiso 1 1 calc R U . . .
C20 C 0.14813(17) 0.3719(3) 0.2679(4) 0.0618(13) Uani 1 1 d . . . . .
H20 H 0.1594 0.4347 0.2410 0.074 Uiso 1 1 calc R U . . .
N1 N 0.05961(12) 0.5132(2) 0.1170(3) 0.0523(10) Uani 1 1 d . . . . .
N2 N 0.2342(2) 0.9913(3) 0.5935(5) 0.1023(18) 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
C1 N2 1.330(7) . ?
C1 C2 1.387(6) . ?
C2 C3 1.373(6) . ?
C3 C4 1.395(7) . ?
C3 C6 1.497(5) . ?
C4 C5 1.378(6) . ?
C5 N2 1.327(7) . ?
C6 C7 1.380(5) . ?
C6 C11 1.384(5) . ?
C7 C8 1.385(5) . ?
C8 C9 1.373(5) . ?
C9 C10 1.380(5) . ?
C9 N1 1.419(4) . ?
C10 C11 1.388(5) . ?
C12 C14 1.387(5) 5_565 ?
C12 C13 1.405(5) . ?
C13 C13 1.363(7) 5_565 ?
C13 N1 1.393(4) . ?
C14 C12 1.387(5) 5_565 ?
C14 N1 1.405(4) . ?
C14 C15 1.455(5) . ?
C15 C16 1.388(5) . ?
C15 C20 1.397(5) . ?
C16 C17 1.400(5) . ?
C17 C18 1.356(6) . ?
C18 C19 1.378(6) . ?
C19 C20 1.398(5) . ?

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
N2 C1 C2 125.5(6) . . ?
C3 C2 C1 118.0(5) . . ?
C2 C3 C4 117.3(4) . . ?
C2 C3 C6 122.6(5) . . ?
C4 C3 C6 120.1(5) . . ?
C5 C4 C3 120.0(6) . . ?
N2 C5 C4 123.4(6) . . ?
C7 C6 C11 118.1(4) . . ?
C7 C6 C3 121.5(4) . . ?
C11 C6 C3 120.4(4) . . ?
C8 C7 C6 120.3(4) . . ?
C9 C8 C7 121.0(4) . . ?
C8 C9 C10 119.6(4) . . ?
C8 C9 N1 119.5(4) . . ?
C10 C9 N1 120.9(4) . . ?
C9 C10 C11 119.1(4) . . ?
C10 C11 C6 121.8(4) . . ?
C14 C12 C13 105.7(3) 5_565 . ?
C13 C13 N1 107.9(4) 5_565 . ?
C13 C13 C12 110.1(4) 5_565 . ?
N1 C13 C12 142.0(3) . . ?
C12 C14 N1 109.2(3) 5_565 . ?
C12 C14 C15 126.8(4) 5_565 . ?
N1 C14 C15 123.7(3) . . ?
C16 C15 C20 116.9(4) . . ?
C16 C15 C14 119.2(4) . . ?
C20 C15 C14 123.8(4) . . ?
C15 C16 C17 122.1(4) . . ?
C18 C17 C16 119.9(5) . . ?
C17 C18 C19 119.7(4) . . ?
C18 C19 C20 120.7(4) . . ?
C15 C20 C19 120.6(4) . . ?
C13 N1 C14 107.1(3) . . ?
C13 N1 C9 122.0(3) . . ?
C14 N1 C9 128.5(3) . . ?
C5 N2 C1 115.8(5) . . ?

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
N2 C1 C2 C3 1.0(8) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C1 C2 C3 C6 177.9(4) . . . . ?
C2 C3 C4 C5 -1.4(8) . . . . ?
C6 C3 C4 C5 -179.0(5) . . . . ?
C3 C4 C5 N2 1.2(9) . . . . ?
C2 C3 C6 C7 -28.4(7) . . . . ?
C4 C3 C6 C7 149.0(5) . . . . ?
C2 C3 C6 C11 153.2(4) . . . . ?
C4 C3 C6 C11 -29.4(6) . . . . ?
C11 C6 C7 C8 1.2(7) . . . . ?
C3 C6 C7 C8 -177.2(4) . . . . ?
C6 C7 C8 C9 0.1(7) . . . . ?
C7 C8 C9 C10 -1.1(7) . . . . ?
C7 C8 C9 N1 175.8(4) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
N1 C9 C10 C11 -176.1(3) . . . . ?
C9 C10 C11 C6 0.5(6) . . . . ?
C7 C6 C11 C10 -1.6(7) . . . . ?
C3 C6 C11 C10 176.9(4) . . . . ?
C14 C12 C13 C13 -1.2(6) 5_565 . . 5_565 ?
C14 C12 C13 N1 179.8(5) 5_565 . . . ?
C12 C14 C15 C16 -24.6(7) 5_565 . . . ?
N1 C14 C15 C16 162.3(4) . . . . ?
C12 C14 C15 C20 150.7(5) 5_565 . . . ?
N1 C14 C15 C20 -22.4(7) . . . . ?
C20 C15 C16 C17 -0.3(7) . . . . ?
C14 C15 C16 C17 175.3(4) . . . . ?
C15 C16 C17 C18 0.8(7) . . . . ?
C16 C17 C18 C19 -0.5(8) . . . . ?
C17 C18 C19 C20 -0.2(7) . . . . ?
C16 C15 C20 C19 -0.5(6) . . . . ?
C14 C15 C20 C19 -175.9(4) . . . . ?
C18 C19 C20 C15 0.8(7) . . . . ?
C13 C13 N1 C14 -0.2(6) 5_565 . . . ?
C12 C13 N1 C14 178.9(6) . . . . ?
C13 C13 N1 C9 -163.7(4) 5_565 . . . ?
C12 C13 N1 C9 15.3(8) . . . . ?
C12 C14 N1 C13 0.9(5) 5_565 . . . ?
C15 C14 N1 C13 175.1(4) . . . . ?
C12 C14 N1 C9 163.0(4) 5_565 . . . ?
C15 C14 N1 C9 -22.8(7) . . . . ?
C8 C9 N1 C13 -61.7(6) . . . . ?
C10 C9 N1 C13 115.2(5) . . . . ?
C8 C9 N1 C14 138.6(4) . . . . ?
C10 C9 N1 C14 -44.6(6) . . . . ?
C4 C5 N2 C1 0.1(9) . . . . ?
C2 C1 N2 C5 -1.2(9) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.043




