# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 1535584'
_audit_update_record             
;
2017-03-02 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ZZ-HPB-CN
_chemical_name_common            ?
_chemical_melting_point          533
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H30 N4'
_chemical_formula_weight         662.76

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      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

_cell_length_a                   14.768(16)
_cell_length_b                   15.377(17)
_cell_length_c                   16.689(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3790(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1062
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      18.26

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_F_000             1384
_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    0.069
_shelx_estimated_absorpt_T_min   0.985
_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      296(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            24688
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.801
_diffrn_reflns_theta_max         25.906
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3638
_reflns_number_gt                1746
_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    ?
_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)+(0.0949P)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         3638
_refine_ls_number_parameters     254
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1904
_refine_ls_wR_factor_gt          0.1442
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.989
_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 0.44943(16) 0.74445(18) 0.66329(15) 0.0537(7) Uani 1 1 d . . . . .
C2 C 0.39877(18) 0.6783(2) 0.63195(19) 0.0748(9) Uani 1 1 d . . . . .
H2 H 0.4176 0.6211 0.6388 0.090 Uiso 1 1 calc R U . . .
C3 C 0.3208(2) 0.6952(3) 0.5907(2) 0.0955(12) Uani 1 1 d . . . . .
H3 H 0.2868 0.6494 0.5701 0.115 Uiso 1 1 calc R U . . .
C4 C 0.2923(2) 0.7789(3) 0.5794(2) 0.0992(12) Uani 1 1 d . . . . .
H4 H 0.2396 0.7901 0.5507 0.119 Uiso 1 1 calc R U . . .
C5 C 0.3414(2) 0.8454(2) 0.6102(2) 0.0899(11) Uani 1 1 d . . . . .
H5 H 0.3225 0.9025 0.6025 0.108 Uiso 1 1 calc R U . . .
C6 C 0.41901(18) 0.8284(2) 0.65266(19) 0.0718(9) Uani 1 1 d . . . . .
H6 H 0.4516 0.8743 0.6746 0.086 Uiso 1 1 calc R U . . .
C7 C 0.53238(15) 0.72746(16) 0.71080(14) 0.0483(6) Uani 1 1 d . . . . .
C8 C 0.59865(16) 0.67328(16) 0.68656(14) 0.0474(6) Uani 1 1 d . . . . .
C9 C 0.60107(15) 0.63563(18) 0.60582(16) 0.0523(7) Uani 1 1 d . . . . .
C10 C 0.58876(18) 0.6851(2) 0.53902(17) 0.0662(8) Uani 1 1 d . . . . .
H10 H 0.5781 0.7445 0.5442 0.079 Uiso 1 1 calc R U . . .
C11 C 0.5919(2) 0.6486(3) 0.4644(2) 0.0863(11) Uani 1 1 d . . . . .
H11 H 0.5834 0.6831 0.4192 0.104 Uiso 1 1 calc R U . . .
C12 C 0.6076(2) 0.5617(3) 0.4562(2) 0.0982(13) Uani 1 1 d . . . . .
H12 H 0.6091 0.5368 0.4055 0.118 Uiso 1 1 calc R U . . .
C13 C 0.6209(2) 0.5118(3) 0.5217(2) 0.0978(12) Uani 1 1 d . . . . .
H13 H 0.6320 0.4525 0.5161 0.117 Uiso 1 1 calc R U . . .
C14 C 0.61800(18) 0.5486(2) 0.59616(19) 0.0724(9) Uani 1 1 d . . . . .
H14 H 0.6277 0.5140 0.6411 0.087 Uiso 1 1 calc R U . . .
C15 C 0.67777(16) 0.65095(15) 0.73712(15) 0.0486(7) Uani 1 1 d . . . . .
C16 C 0.76409(16) 0.65269(17) 0.70416(15) 0.0550(7) Uani 1 1 d . . . . .
H16 H 0.7708 0.6653 0.6500 0.066 Uiso 1 1 calc R U . . .
C17 C 0.83917(18) 0.63635(17) 0.74917(16) 0.0571(7) Uani 1 1 d . . . . .
H17 H 0.8961 0.6383 0.7255 0.069 Uiso 1 1 calc R U . . .
C18 C 0.83143(17) 0.61694(17) 0.82933(16) 0.0553(7) Uani 1 1 d . . . . .
C19 C 0.74544(18) 0.61287(17) 0.86168(16) 0.0623(8) Uani 1 1 d . . . . .
H19 H 0.7386 0.5989 0.9156 0.075 Uiso 1 1 calc R U . . .
C20 C 0.67059(17) 0.62884(17) 0.81666(16) 0.0563(7) Uani 1 1 d . . . . .
H20 H 0.6136 0.6247 0.8401 0.068 Uiso 1 1 calc R U . . .
C21 C 0.90707(19) 0.60152(19) 0.88230(17) 0.0691(8) Uani 1 1 d . . . . .
H21 H 0.8906 0.5935 0.9356 0.083 Uiso 1 1 calc R U . . .
C22 C 0.9934(2) 0.5967(2) 0.86977(17) 0.0830(10) Uani 1 1 d D U . . .
C24 C 1.0564(2) 0.5798(2) 0.9329(2) 0.0835(10) Uani 1 1 d D . . . .
C23A C 1.0297(4) 0.5693(6) 0.7948(3) 0.095(2) Uani 0.585(5) 1 d D U P A 1
N1A N 1.0611(4) 0.5555(6) 0.7359(3) 0.153(3) Uani 0.585(5) 1 d D U P A 1
C23B C 1.0331(6) 0.6503(8) 0.8041(5) 0.114(3) Uani 0.415(5) 1 d D U P A 2
N1B N 1.0635(6) 0.6893(7) 0.7515(5) 0.157(4) Uani 0.415(5) 1 d D U P A 2
N2 N 1.10619(19) 0.5677(2) 0.98256(19) 0.1080(11) Uani 1 1 d 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 C2 1.367(4) . ?
C1 C6 1.378(4) . ?
C1 C7 1.482(4) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.347(3) . ?
C7 C7 1.481(5) 4_566 ?
C8 C9 1.467(4) . ?
C8 C15 1.481(3) . ?
C9 C10 1.362(4) . ?
C9 C14 1.372(4) . ?
C10 C11 1.366(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.350(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.374(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.363(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(4) . ?
C18 C21 1.444(4) . ?
C19 C20 1.359(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.294(4) . ?
C21 H21 0.9300 . ?
C22 C23A 1.424(5) . ?
C22 C24 1.430(4) . ?
C22 C23B 1.492(7) . ?
C24 N2 1.123(3) . ?
C23A N1A 1.109(6) . ?
C23B N1B 1.153(7) . ?
N1B N1B 1.87(2) 4_566 ?

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
C2 C1 C6 118.0(3) . . ?
C2 C1 C7 121.7(3) . . ?
C6 C1 C7 120.2(2) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C8 C7 C1 123.3(2) . . ?
C8 C7 C7 123.69(19) . 4_566 ?
C1 C7 C7 112.96(17) . 4_566 ?
C7 C8 C9 122.5(2) . . ?
C7 C8 C15 123.0(2) . . ?
C9 C8 C15 114.4(2) . . ?
C10 C9 C14 118.3(3) . . ?
C10 C9 C8 121.9(3) . . ?
C14 C9 C8 119.8(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C20 C15 C16 117.3(2) . . ?
C20 C15 C8 123.1(2) . . ?
C16 C15 C8 119.6(2) . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 117.8(2) . . ?
C17 C18 C21 124.5(2) . . ?
C19 C18 C21 117.7(3) . . ?
C20 C19 C18 121.6(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C15 121.1(2) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C22 C21 C18 132.3(3) . . ?
C22 C21 H21 113.9 . . ?
C18 C21 H21 113.9 . . ?
C21 C22 C23A 122.0(3) . . ?
C21 C22 C24 122.2(3) . . ?
C23A C22 C24 110.4(4) . . ?
C21 C22 C23B 118.3(5) . . ?
C24 C22 C23B 112.7(4) . . ?
N2 C24 C22 179.1(4) . . ?
N1A C23A C22 173.5(9) . . ?
N1B C23B C22 177.6(14) . . ?
C23B N1B N1B 122.7(13) . 4_566 ?

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 0.6(5) . . . . ?
C7 C1 C2 C3 177.7(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C7 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C7 C8 49.1(4) . . . . ?
C6 C1 C7 C8 -133.9(3) . . . . ?
C2 C1 C7 C7 -127.9(3) . . . 4_566 ?
C6 C1 C7 C7 49.1(4) . . . 4_566 ?
C1 C7 C8 C9 9.0(4) . . . . ?
C7 C7 C8 C9 -174.4(3) 4_566 . . . ?
C1 C7 C8 C15 -174.8(2) . . . . ?
C7 C7 C8 C15 1.8(4) 4_566 . . . ?
C7 C8 C9 C10 47.9(4) . . . . ?
C15 C8 C9 C10 -128.6(3) . . . . ?
C7 C8 C9 C14 -133.5(3) . . . . ?
C15 C8 C9 C14 50.0(3) . . . . ?
C14 C9 C10 C11 0.9(4) . . . . ?
C8 C9 C10 C11 179.5(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C12 C13 C14 C9 0.5(5) . . . . ?
C10 C9 C14 C13 -1.2(4) . . . . ?
C8 C9 C14 C13 -179.8(3) . . . . ?
C7 C8 C15 C20 45.6(4) . . . . ?
C9 C8 C15 C20 -137.9(3) . . . . ?
C7 C8 C15 C16 -133.8(3) . . . . ?
C9 C8 C15 C16 42.7(3) . . . . ?
C20 C15 C16 C17 -2.4(4) . . . . ?
C8 C15 C16 C17 177.1(2) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C16 C17 C18 C21 -177.9(3) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C21 C18 C19 C20 178.2(3) . . . . ?
C18 C19 C20 C15 -0.9(4) . . . . ?
C16 C15 C20 C19 2.6(4) . . . . ?
C8 C15 C20 C19 -176.8(2) . . . . ?
C17 C18 C21 C22 -4.6(5) . . . . ?
C19 C18 C21 C22 176.2(3) . . . . ?
C18 C21 C22 C23A -28.0(7) . . . . ?
C18 C21 C22 C24 -179.5(3) . . . . ?
C18 C21 C22 C23B 31.5(8) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_properties_physical    ', Light-sensitive'
_exptl_crystal_preparation       ', Luminescent'
