# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_p1
_database_code_depnum_ccdc_archive 'CCDC 892287'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   26.930(6)
_cell_length_b                   6.9117(14)
_cell_length_c                   9.772(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.45(3)
_cell_angle_gamma                90.00
_cell_volume                     1788.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3106
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      24.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   Process-auto

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13195
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         24.98
_reflns_number_total             3106
_reflns_number_gt                1680
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Process-auto
_computing_cell_refinement       Process-auto
_computing_data_reduction        Process-auto
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1958P)²+0.4187P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3106
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.3333
_refine_ls_wR_factor_gt          0.3063
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4194(15) 0.476(7) 0.711(4) 0.086(7) Uani 0.50 1 d P . .
N1' N 0.4032(15) 0.468(7) 0.662(4) 0.086(7) Uani 0.50 1 d P . .
N2 N 0.0955(19) 0.018(8) 0.254(5) 0.089(9) Uani 0.50 1 d P . .
N2' N 0.0814(19) 0.027(8) 0.289(5) 0.089(9) Uani 0.50 1 d P . .
C1 C 0.52254(17) 0.1429(7) 0.4353(5) 0.0568(13) Uani 1 1 d . . .
H1 H 0.5374 0.2417 0.3922 0.080 Uiso 1 1 calc . . .
C2 C 0.48655(18) 0.1880(6) 0.5150(6) 0.0556(12) Uani 1 1 d . . .
H2 H 0.4778 0.3168 0.5244 0.080 Uiso 1 1 calc . . .
C3 C 0.46326(15) 0.0461(7) 0.5811(5) 0.0499(12) Uani 1 1 d . . .
C4 C 0.42418(16) 0.1012(6) 0.6669(5) 0.0495(11) Uani 1 1 d . . .
C5 C 0.4164(2) 0.3010(8) 0.6788(7) 0.0721(17) Uani 1 1 d . . .
C6 C 0.39811(15) -0.0246(6) 0.7271(5) 0.0455(11) Uani 1 1 d . . .
H6 H 0.4064 -0.1523 0.7114 0.080 Uiso 1 1 calc . . .
C7 C 0.35921(15) -0.0076(6) 0.8127(4) 0.0433(11) Uani 1 1 d . . .
C8 C 0.3439(2) 0.1685(8) 0.8627(6) 0.0657(15) Uani 1 1 d . . .
H8 H 0.3589 0.2834 0.8419 0.080 Uiso 1 1 calc . . .
C9 C 0.3060(2) 0.1717(9) 0.9439(6) 0.0757(17) Uani 1 1 d . . .
H9 H 0.2958 0.2886 0.9770 0.080 Uiso 1 1 calc . . .
C10 C 0.28396(18) 0.0000(9) 0.9747(6) 0.0690(16) Uani 1 1 d . . .
H10 H 0.2585 0.0018 1.0274 0.080 Uiso 1 1 calc . . .
C11 C 0.2992(2) -0.1698(9) 0.9285(6) 0.0767(17) Uani 1 1 d . . .
H11 H 0.2846 -0.2848 0.9506 0.080 Uiso 1 1 calc . . .
C12 C 0.33627(19) -0.1732(8) 0.8489(6) 0.0622(14) Uani 1 1 d . . .
H12 H 0.3463 -0.2919 0.8182 0.080 Uiso 1 1 calc . . .
C13 C 0.02211(17) 0.6418(7) 0.0888(5) 0.0544(12) Uani 1 1 d . . .
H13 H 0.0369 0.7391 0.1482 0.080 Uiso 1 1 calc . . .
C14 C 0.01365(17) 0.3100(6) 0.0255(5) 0.0524(12) Uani 1 1 d . . .
H14 H 0.0226 0.1809 0.0415 0.080 Uiso 1 1 calc . . .
C15 C 0.03663(14) 0.4503(7) 0.1175(4) 0.0444(11) Uani 1 1 d . . .
C16 C 0.07526(15) 0.3944(6) 0.2406(5) 0.0471(11) Uani 1 1 d . . .
C17 C 0.0833(2) 0.1885(8) 0.2600(6) 0.0702(17) Uani 1 1 d . . .
C18 C 0.10190(16) 0.5185(6) 0.3289(5) 0.0453(11) Uani 1 1 d . . .
H18 H 0.0944 0.6475 0.3075 0.080 Uiso 1 1 calc . . .
C19 C 0.14060(15) 0.4915(6) 0.4529(4) 0.0417(10) Uani 1 1 d . . .
C20 C 0.1538(2) 0.3156(8) 0.5158(6) 0.0659(15) Uani 1 1 d . . .
H20 H 0.1378 0.2027 0.4795 0.080 Uiso 1 1 calc . . .
C21 C 0.1921(2) 0.3086(9) 0.6359(6) 0.0737(17) Uani 1 1 d . . .
H21 H 0.2011 0.1907 0.6791 0.080 Uiso 1 1 calc . . .
C22 C 0.21592(18) 0.4766(10) 0.6894(6) 0.0685(16) Uani 1 1 d . . .
H22 H 0.2416 0.4713 0.7671 0.080 Uiso 1 1 calc . . .
C23 C 0.2020(2) 0.6479(9) 0.6287(6) 0.0766(18) Uani 1 1 d . . .
H23 H 0.2176 0.7607 0.6662 0.080 Uiso 1 1 calc . . .
C24 C 0.16505(18) 0.6581(8) 0.5129(5) 0.0607(14) Uani 1 1 d . . .
H24 H 0.1560 0.7780 0.4730 0.080 Uiso 1 1 calc . . .


_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 N1' 0.59(5) . ?
N1 C5 1.25(4) . ?
N1' C5 1.21(5) . ?
N2 N2' 0.56(7) . ?
N2 C17 1.23(5) . ?
N2' C17 1.15(6) . ?
C1 C3 1.379(7) 3_656 ?
C1 C2 1.385(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(7) . ?
C2 H2 0.9300 . ?
C3 C1 1.379(7) 3_656 ?
C3 C4 1.508(6) . ?
C4 C6 1.321(6) . ?
C4 C5 1.405(7) . ?
C6 C7 1.459(6) . ?
C6 H6 0.9300 . ?
C7 C12 1.377(7) . ?
C7 C8 1.401(6) . ?
C8 C9 1.401(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.348(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.377(7) 3_565 ?
C13 C15 1.394(6) . ?
C13 H13 0.9300 . ?
C14 C13 1.377(7) 3_565 ?
C14 C15 1.389(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.491(6) . ?
C16 C18 1.331(6) . ?
C16 C17 1.447(7) . ?
C18 C19 1.460(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(6) . ?
C19 C24 1.401(6) . ?
C20 C21 1.415(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.346(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
N1' N1 C5 72(8) . . ?
N1 N1' C5 80(9) . . ?
N2' N2 C17 69(10) . . ?
N2 N2' C17 84(10) . . ?
C3 C1 C2 121.0(4) 3_656 . ?
C3 C1 H1 119.5 3_656 . ?
C2 C1 H1 119.5 . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C1 C3 C2 117.3(4) 3_656 . ?
C1 C3 C4 122.7(4) 3_656 . ?
C2 C3 C4 120.1(4) . . ?
C6 C4 C5 120.7(4) . . ?
C6 C4 C3 124.2(4) . . ?
C5 C4 C3 115.0(4) . . ?
N1' C5 N1 28(2) . . ?
N1' C5 C4 166.1(14) . . ?
N1 C5 C4 165.8(16) . . ?
C4 C6 C7 134.2(4) . . ?
C4 C6 H6 112.9 . . ?
C7 C6 H6 112.9 . . ?
C12 C7 C8 117.3(4) . . ?
C12 C7 C6 118.9(4) . . ?
C8 C7 C6 123.8(4) . . ?
C7 C8 C9 120.1(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.1(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 122.5(5) . . ?
C11 C12 H12 118.7 . . ?
C7 C12 H12 118.7 . . ?
C14 C13 C15 121.5(4) 3_565 . ?
C14 C13 H13 119.2 3_565 . ?
C15 C13 H13 119.2 . . ?
C13 C14 C15 121.3(4) 3_565 . ?
C13 C14 H14 119.3 3_565 . ?
C15 C14 H14 119.3 . . ?
C14 C15 C13 117.2(4) . . ?
C14 C15 C16 120.3(4) . . ?
C13 C15 C16 122.5(4) . . ?
C18 C16 C17 119.9(4) . . ?
C18 C16 C15 124.8(4) . . ?
C17 C16 C15 115.2(4) . . ?
N2' C17 N2 27(3) . . ?
N2' C17 C16 165.9(19) . . ?
N2 C17 C16 166(2) . . ?
C16 C18 C19 132.5(4) . . ?
C16 C18 H18 113.7 . . ?
C19 C18 H18 113.7 . . ?
C20 C19 C24 118.3(4) . . ?
C20 C19 C18 124.8(4) . . ?
C24 C19 C18 116.9(4) . . ?
C19 C20 C21 119.3(5) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.9(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.9(5) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 121.3(5) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.064
