# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_l8
_database_code_depnum_ccdc_archive 'CCDC 971201'
_audit_update_record             
;
2013-11-09 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H30 N2'
_chemical_formula_weight         454.59

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   13.740(5)
_cell_length_b                   12.487(5)
_cell_length_c                   15.071(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.349(5)
_cell_angle_gamma                90.00
_cell_volume                     2543.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18990
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.92
_reflns_number_total             4908
_reflns_number_gt                3228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4908
_refine_ls_number_parameters     318
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1742
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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 0.96212(11) 1.09853(11) 0.23411(10) 0.0609(4) Uani 1 1 d . . .
N2 N 1.10316(12) 1.39966(13) -0.06797(11) 0.0749(5) Uani 1 1 d U . .
C23 C 0.95112(12) 1.09598(13) 0.14866(12) 0.0597(4) Uani 1 1 d . . .
H23 H 0.9173 1.0381 0.1189 0.072 Uiso 1 1 calc R . .
C24 C 0.98776(12) 1.17719(13) 0.09456(11) 0.0573(4) Uani 1 1 d . . .
C17 C 0.86655(13) 0.83173(12) 0.36761(11) 0.0555(4) Uani 1 1 d . . .
C25 C 1.03756(12) 1.26790(13) 0.13139(12) 0.0581(4) Uani 1 1 d . . .
H25 H 1.0452 1.2796 0.1932 0.070 Uiso 1 1 calc R . .
C26 C 1.07574(13) 1.34075(13) 0.07875(12) 0.0611(5) Uani 1 1 d . . .
H26 H 1.1086 1.4008 0.1057 0.073 Uiso 1 1 calc R . .
C27 C 1.06630(12) 1.32675(14) -0.01473(12) 0.0606(5) Uani 1 1 d . . .
C19 C 0.98232(13) 0.97353(14) 0.35669(11) 0.0624(5) Uani 1 1 d . . .
H19 H 1.0404 1.0093 0.3810 0.075 Uiso 1 1 calc R . .
C18 C 0.95437(13) 0.88475(14) 0.40016(12) 0.0614(5) Uani 1 1 d . . .
H18 H 0.9950 0.8600 0.4522 0.074 Uiso 1 1 calc R . .
C29 C 0.97899(14) 1.16250(15) 0.00221(12) 0.0670(5) Uani 1 1 d . . .
H29 H 0.9459 1.1023 -0.0242 0.080 Uiso 1 1 calc R . .
C20 C 0.92567(12) 1.01026(12) 0.27773(11) 0.0545(4) Uani 1 1 d . . .
C10 C 0.84692(13) 0.48491(16) 0.48077(14) 0.0718(6) Uani 1 1 d . . .
C21 C 0.83692(14) 0.96006(15) 0.24646(12) 0.0690(5) Uani 1 1 d . . .
H21 H 0.7962 0.9852 0.1946 0.083 Uiso 1 1 calc R . .
C28 C 1.01754(14) 1.23396(15) -0.05144(12) 0.0687(5) Uani 1 1 d . . .
H28 H 1.0112 1.2206 -0.1129 0.082 Uiso 1 1 calc R . .
C1 C 0.83751(13) 0.58742(16) 0.51626(14) 0.0739(6) Uani 1 1 d . . .
C16 C 0.83315(13) 0.73702(14) 0.41112(12) 0.0651(5) Uani 1 1 d . . .
H16 H 0.7694 0.7142 0.3871 0.078 Uiso 1 1 calc R . .
C9 C 0.80079(14) 0.39531(16) 0.51569(14) 0.0745(6) Uani 1 1 d . . .
C22 C 0.80800(14) 0.87330(15) 0.29115(13) 0.0714(5) Uani 1 1 d . . .
H22 H 0.7472 0.8415 0.2694 0.086 Uiso 1 1 calc R . .
C2 C 0.78888(14) 0.60081(15) 0.58979(14) 0.0722(6) Uani 1 1 d U . .
C7 C 0.74330(14) 0.51063(17) 0.62497(13) 0.0725(6) Uani 1 1 d . . .
C11 C 0.90013(15) 0.4646(2) 0.41039(16) 0.0893(7) Uani 1 1 d . . .
H11 H 0.9308 0.5213 0.3865 0.107 Uiso 1 1 calc R . .
C30 C 1.14289(16) 1.50300(15) -0.03217(15) 0.0821(6) Uani 1 1 d U . .
H30A H 1.1060 1.5270 0.0133 0.098 Uiso 1 1 calc R . .
H30B H 1.1333 1.5553 -0.0806 0.098 Uiso 1 1 calc R . .
C8 C 0.74988(15) 0.41161(16) 0.58609(15) 0.0777(6) Uani 1 1 d . . .
H8 H 0.7190 0.3535 0.6079 0.093 Uiso 1 1 calc R . .
C6 C 0.69174(16) 0.5276(2) 0.69706(16) 0.0891(7) Uani 1 1 d . . .
H6 H 0.6611 0.4698 0.7196 0.107 Uiso 1 1 calc R . .
C32 C 1.09704(17) 1.38016(19) -0.16501(14) 0.0894(7) Uani 1 1 d . . .
H32A H 1.1097 1.3050 -0.1745 0.107 Uiso 1 1 calc R . .
H32B H 1.1480 1.4214 -0.1864 0.107 Uiso 1 1 calc R . .
C12 C 0.90764(16) 0.3654(2) 0.37703(17) 0.0975(7) Uani 1 1 d . . .
H12 H 0.9445 0.3549 0.3317 0.117 Uiso 1 1 calc R . .
C3 C 0.78132(17) 0.70194(19) 0.63165(17) 0.0898(7) Uani 1 1 d U . .
H3 H 0.8111 0.7613 0.6106 0.108 Uiso 1 1 calc R . .
C15 C 0.87682(15) 0.68206(17) 0.47550(16) 0.0951(8) Uani 1 1 d . . .
H15 H 0.9409 0.7030 0.5004 0.114 Uiso 1 1 calc R . .
C13 C 0.86059(18) 0.2776(2) 0.40970(18) 0.0978(7) Uani 1 1 d . . .
H13 H 0.8648 0.2098 0.3853 0.117 Uiso 1 1 calc R . .
C14 C 0.80944(17) 0.29302(18) 0.47669(18) 0.0903(7) Uani 1 1 d . . .
H14 H 0.7786 0.2347 0.4983 0.108 Uiso 1 1 calc R . .
C31 C 1.25054(16) 1.49862(16) 0.00867(17) 0.0917(7) Uani 1 1 d . . .
H31A H 1.2600 1.4511 0.0596 0.138 Uiso 1 1 calc R . .
H31B H 1.2732 1.5690 0.0280 0.138 Uiso 1 1 calc R . .
H31C H 1.2874 1.4729 -0.0354 0.138 Uiso 1 1 calc R . .
C5 C 0.68588(19) 0.6252(3) 0.73390(17) 0.1002(7) Uani 1 1 d . . .
H5 H 0.6513 0.6340 0.7811 0.120 Uiso 1 1 calc R . .
C33 C 0.9968(2) 1.4101(2) -0.21957(16) 0.1163(9) Uani 1 1 d . . .
H33A H 0.9455 1.3787 -0.1925 0.174 Uiso 1 1 calc R . .
H33B H 0.9919 1.3840 -0.2801 0.174 Uiso 1 1 calc R . .
H33C H 0.9898 1.4866 -0.2206 0.174 Uiso 1 1 calc R . .
C4 C 0.7323(2) 0.7144(2) 0.70091(18) 0.1009(8) Uani 1 1 d . . .
H4 H 0.7290 0.7815 0.7270 0.121 Uiso 1 1 calc R . .


_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 C23 1.270(2) . ?
N1 C20 1.420(2) . ?
N2 C27 1.369(2) . ?
N2 C30 1.466(3) . ?
N2 C32 1.470(3) . ?
C23 C24 1.447(2) . ?
C24 C25 1.387(2) . ?
C24 C29 1.387(3) . ?
C17 C22 1.382(2) . ?
C17 C18 1.386(2) . ?
C17 C16 1.465(2) . ?
C25 C26 1.372(2) . ?
C26 C27 1.402(3) . ?
C27 C28 1.402(3) . ?
C19 C18 1.377(2) . ?
C19 C20 1.378(2) . ?
C29 C28 1.373(2) . ?
C20 C21 1.377(2) . ?
C10 C1 1.402(3) . ?
C10 C11 1.415(3) . ?
C10 C9 1.432(3) . ?
C21 C22 1.372(2) . ?
C1 C2 1.403(3) . ?
C1 C15 1.478(2) . ?
C16 C15 1.250(2) . ?
C9 C8 1.387(3) . ?
C9 C14 1.420(3) . ?
C2 C3 1.424(3) . ?
C2 C7 1.436(3) . ?
C7 C8 1.378(3) . ?
C7 C6 1.416(3) . ?
C11 C12 1.347(3) . ?
C30 C31 1.498(3) . ?
C6 C5 1.348(3) . ?
C32 C33 1.518(3) . ?
C12 C13 1.406(3) . ?
C3 C4 1.349(3) . ?
C13 C14 1.343(3) . ?
C5 C4 1.417(4) . ?

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
C23 N1 C20 117.54(15) . . ?
C27 N2 C30 121.47(17) . . ?
C27 N2 C32 120.78(16) . . ?
C30 N2 C32 117.58(16) . . ?
N1 C23 C24 124.32(16) . . ?
C25 C24 C29 117.21(15) . . ?
C25 C24 C23 122.92(16) . . ?
C29 C24 C23 119.76(16) . . ?
C22 C17 C18 117.05(15) . . ?
C22 C17 C16 119.59(15) . . ?
C18 C17 C16 123.35(15) . . ?
C26 C25 C24 121.51(17) . . ?
C25 C26 C27 121.49(17) . . ?
N2 C27 C28 121.28(17) . . ?
N2 C27 C26 121.90(17) . . ?
C28 C27 C26 116.81(15) . . ?
C18 C19 C20 121.08(16) . . ?
C19 C18 C17 121.03(15) . . ?
C28 C29 C24 122.13(17) . . ?
C21 C20 C19 118.17(15) . . ?
C21 C20 N1 124.01(15) . . ?
C19 C20 N1 117.81(15) . . ?
C1 C10 C11 123.04(19) . . ?
C1 C10 C9 119.7(2) . . ?
C11 C10 C9 117.2(2) . . ?
C22 C21 C20 120.56(16) . . ?
C29 C28 C27 120.83(17) . . ?
C10 C1 C2 119.98(17) . . ?
C10 C1 C15 120.4(2) . . ?
C2 C1 C15 119.6(2) . . ?
C15 C16 C17 130.16(18) . . ?
C8 C9 C14 122.68(19) . . ?
C8 C9 C10 118.9(2) . . ?
C14 C9 C10 118.4(2) . . ?
C21 C22 C17 121.96(17) . . ?
C1 C2 C3 122.59(19) . . ?
C1 C2 C7 120.0(2) . . ?
C3 C2 C7 117.4(2) . . ?
C8 C7 C6 122.74(19) . . ?
C8 C7 C2 118.7(2) . . ?
C6 C7 C2 118.5(2) . . ?
C12 C11 C10 122.0(2) . . ?
N2 C30 C31 113.22(17) . . ?
C7 C8 C9 122.52(18) . . ?
C5 C6 C7 121.8(2) . . ?
N2 C32 C33 112.47(19) . . ?
C11 C12 C13 121.0(2) . . ?
C4 C3 C2 122.1(2) . . ?
C16 C15 C1 126.94(18) . . ?
C14 C13 C12 119.2(3) . . ?
C13 C14 C9 122.3(2) . . ?
C6 C5 C4 120.2(3) . . ?
C3 C4 C5 119.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.92
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
