# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ICz5Cz
_database_code_depnum_ccdc_archive 'CCDC 1568697'
_audit_update_record             
;
2017-08-13 deposited with the CCDC.
2018-08-28 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            'C30 H18 N2'
_chemical_formula_weight         406.46

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                   9.5240(4)
_cell_length_b                   27.7354(10)
_cell_length_c                   8.2808(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.572(5)
_cell_angle_gamma                90
_cell_volume                     2061.00(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5240
_cell_measurement_theta_min      3.1600
_cell_measurement_theta_max      73.6790

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.593
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9005
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.187
_diffrn_reflns_theta_max         73.807
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3949
_reflns_number_gt                3505
_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       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (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)+2.9144P] 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-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.00146(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3949
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 0.7652(2) 0.46684(8) 0.0571(3) 0.0323(5) Uani 1 1 d . . . . .
C1 C 0.7650(3) 0.42957(9) 0.1712(3) 0.0302(6) Uani 1 1 d . . . . .
N2 N 0.7148(2) 0.33956(8) 0.5519(3) 0.0355(5) Uani 1 1 d . . . . .
C2 C 0.8211(3) 0.38343(10) 0.1842(3) 0.0359(6) Uani 1 1 d . . . . .
H2 H 0.8702 0.3722 0.1087 0.043 Uiso 1 1 calc R U . . .
C3 C 0.8035(3) 0.35383(10) 0.3115(3) 0.0372(6) Uani 1 1 d . . . . .
H3 H 0.8405 0.3217 0.3230 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6760(3) 0.41711(10) 0.4108(3) 0.0316(6) Uani 1 1 d . . . . .
H5 H 0.6281 0.4280 0.4879 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7320(3) 0.37076(10) 0.4229(3) 0.0338(6) Uani 1 1 d . . . . .
C6 C 0.6909(3) 0.44749(9) 0.2842(3) 0.0300(5) Uani 1 1 d . . . . .
C7 C 0.6972(3) 0.50560(9) 0.1000(3) 0.0307(6) Uani 1 1 d . . . . .
C8 C 0.6479(3) 0.49744(10) 0.2363(3) 0.0310(6) Uani 1 1 d . . . . .
C9 C 0.5791(3) 0.53764(10) 0.2808(3) 0.0348(6) Uani 1 1 d . . . . .
H9 H 0.5415 0.5362 0.3735 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5676(3) 0.57992(10) 0.1846(4) 0.0383(6) Uani 1 1 d . . . . .
H10 H 0.5199 0.6069 0.2146 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6210(3) 0.58541(10) 0.0476(3) 0.0372(6) Uani 1 1 d . . . . .
H11 H 0.6100 0.6151 -0.0124 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6909(3) 0.54611(10) 0.0011(3) 0.0334(6) Uani 1 1 d . . . . .
C13 C 0.8110(3) 0.48156(11) -0.0795(3) 0.0348(6) Uani 1 1 d . . . . .
C14 C 0.7657(3) 0.53012(11) -0.1193(3) 0.0357(6) Uani 1 1 d . . . . .
C15 C 0.8020(3) 0.55311(12) -0.2503(3) 0.0424(7) Uani 1 1 d . . . . .
H15 H 0.7736 0.5857 -0.2793 0.051 Uiso 1 1 calc R U . . .
C16 C 0.8797(3) 0.52787(13) -0.3370(4) 0.0482(8) Uani 1 1 d . . . . .
H16 H 0.9043 0.5433 -0.4264 0.058 Uiso 1 1 calc R U . . .
C17 C 0.9224(3) 0.48039(13) -0.2956(4) 0.0472(8) Uani 1 1 d . . . . .
H17 H 0.9761 0.4642 -0.3574 0.057 Uiso 1 1 calc R U . . .
C18 C 0.8892(3) 0.45571(12) -0.1666(3) 0.0399(7) Uani 1 1 d . . . . .
H18 H 0.9181 0.4231 -0.1394 0.048 Uiso 1 1 calc R U . . .
C19 C 0.8269(3) 0.32419(10) 0.6991(4) 0.0397(7) Uani 1 1 d . . . . .
C20 C 0.9800(4) 0.33101(12) 0.7473(4) 0.0500(8) Uani 1 1 d . . . . .
H20 H 1.0238 0.3482 0.6770 0.060 Uiso 1 1 calc R U . . .
C21 C 1.0661(4) 0.31132(14) 0.9044(5) 0.0633(10) Uani 1 1 d . . . . .
H21 H 1.1713 0.3149 0.9415 0.076 Uiso 1 1 calc R U . . .
C22 C 1.0019(5) 0.28663(14) 1.0082(4) 0.0657(11) Uani 1 1 d . . . . .
H22 H 1.0641 0.2741 1.1150 0.079 Uiso 1 1 calc R U . . .
C23 C 0.8516(5) 0.27993(12) 0.9602(4) 0.0585(10) Uani 1 1 d . . . . .
H23 H 0.8095 0.2626 1.0318 0.070 Uiso 1 1 calc R U . . .
C24 C 0.7606(4) 0.29898(10) 0.8042(4) 0.0439(7) Uani 1 1 d . . . . .
C25 C 0.6027(4) 0.30027(10) 0.7186(4) 0.0435(7) Uani 1 1 d . . . . .
C26 C 0.4799(5) 0.28287(12) 0.7588(5) 0.0601(10) Uani 1 1 d . . . . .
H26 H 0.4936 0.2657 0.8623 0.072 Uiso 1 1 calc R U . . .
C27 C 0.3394(5) 0.29126(14) 0.6449(6) 0.0677(11) Uani 1 1 d . . . . .
H27 H 0.2555 0.2799 0.6712 0.081 Uiso 1 1 calc R U . . .
C28 C 0.3172(4) 0.31570(13) 0.4935(5) 0.0587(9) Uani 1 1 d . . . . .
H28 H 0.2184 0.3206 0.4177 0.070 Uiso 1 1 calc R U . . .
C29 C 0.4353(3) 0.33337(11) 0.4490(4) 0.0444(7) Uani 1 1 d . . . . .
H29 H 0.4196 0.3501 0.3443 0.053 Uiso 1 1 calc R U . . .
C30 C 0.5784(3) 0.32557(10) 0.5645(4) 0.0362(6) 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 C7 1.362(3) . ?
N1 C1 1.401(3) . ?
N1 C13 1.403(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.436(3) . ?
N2 C19 1.391(3) . ?
N2 C30 1.393(3) . ?
N2 C4 1.427(3) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(4) . ?
C3 H3 0.9500 . ?
C5 C4 1.383(4) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 C8 1.462(4) . ?
C7 C8 1.378(4) . ?
C7 C12 1.380(4) . ?
C8 C9 1.404(4) . ?
C9 C10 1.401(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(4) . ?
C11 H11 0.9500 . ?
C12 C14 1.475(4) . ?
C13 C18 1.395(4) . ?
C13 C14 1.419(4) . ?
C14 C15 1.398(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.391(4) . ?
C19 C24 1.418(4) . ?
C20 C21 1.396(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.364(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.432(5) . ?
C25 C26 1.405(5) . ?
C25 C30 1.405(4) . ?
C26 C27 1.374(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.395(4) . ?
C29 H29 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
C7 N1 C1 107.3(2) . . ?
C7 N1 C13 106.5(2) . . ?
C1 N1 C13 146.1(2) . . ?
C2 C1 N1 130.5(2) . . ?
C2 C1 C6 122.2(2) . . ?
N1 C1 C6 107.2(2) . . ?
C19 N2 C30 108.1(2) . . ?
C19 N2 C4 126.5(2) . . ?
C30 N2 C4 124.7(2) . . ?
C1 C2 C3 117.8(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 N2 118.7(2) . . ?
C3 C4 N2 119.6(2) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C8 133.6(2) . . ?
C1 C6 C8 107.8(2) . . ?
N1 C7 C8 113.9(2) . . ?
N1 C7 C12 114.7(2) . . ?
C8 C7 C12 131.3(3) . . ?
C7 C8 C9 113.7(2) . . ?
C7 C8 C6 103.7(2) . . ?
C9 C8 C6 142.6(2) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 C9 124.9(3) . . ?
C11 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C7 C12 C11 113.7(2) . . ?
C7 C12 C14 102.8(2) . . ?
C11 C12 C14 143.5(3) . . ?
C18 C13 N1 129.1(3) . . ?
C18 C13 C14 122.8(3) . . ?
N1 C13 C14 108.1(2) . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 C12 133.5(3) . . ?
C13 C14 C12 107.9(2) . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 122.3(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C13 116.2(3) . . ?
C17 C18 H18 121.9 . . ?
C13 C18 H18 121.9 . . ?
C20 C19 N2 129.3(3) . . ?
C20 C19 C24 122.0(3) . . ?
N2 C19 C24 108.7(3) . . ?
C19 C20 C21 116.5(3) . . ?
C19 C20 H20 121.8 . . ?
C21 C20 H20 121.8 . . ?
C22 C21 C20 121.8(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C21 121.6(3) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 118.9(3) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C19 119.2(3) . . ?
C23 C24 C25 133.7(3) . . ?
C19 C24 C25 107.1(3) . . ?
C26 C25 C30 119.3(3) . . ?
C26 C25 C24 133.9(3) . . ?
C30 C25 C24 106.7(3) . . ?
C27 C26 C25 118.4(3) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C26 C27 C28 121.7(3) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C27 C28 C29 121.7(4) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C28 C29 C30 117.2(3) . . ?
C28 C29 H29 121.4 . . ?
C30 C29 H29 121.4 . . ?
N2 C30 C29 128.8(3) . . ?
N2 C30 C25 109.5(3) . . ?
C29 C30 C25 121.7(3) . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.050



