# 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_cb74_0m
_database_code_depnum_ccdc_archive 'CCDC 1486395'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 N2'
_chemical_formula_weight         280.32

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   19.293(3)
_cell_length_b                   4.0674(7)
_cell_length_c                   20.370(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.107(3)
_cell_angle_gamma                90
_cell_volume                     1410.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3621
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.54

_exptl_crystal_description       'needle frag'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   0.537
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23666
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2577
_reflns_number_gt                1839
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0621P)²+1.0822P] 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         2577
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.88487(13) 0.3609(6) 0.14523(11) 0.0262(5) Uani 1 1 d . . . . .
H1 H 0.8452 0.4657 0.1528 0.031 Uiso 1 1 calc R U . . .
C2 C 0.96208(13) 0.3914(6) 0.19796(12) 0.0298(6) Uani 1 1 d . . . . .
H2 H 0.9752 0.5133 0.2420 0.036 Uiso 1 1 calc R U . . .
C3 C 1.02232(13) 0.2433(6) 0.18739(12) 0.0304(6) Uani 1 1 d . . . . .
H3 H 1.0756 0.2670 0.2244 0.037 Uiso 1 1 calc R U . . .
C4 C 1.00497(13) 0.0685(6) 0.12532(12) 0.0286(5) Uani 1 1 d . . . . .
H4 H 1.0462 -0.0298 0.1191 0.034 Uiso 1 1 calc R U . . .
C4A C 0.92527(12) 0.0291(6) 0.06862(11) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.81318(13) -0.3516(6) -0.12086(12) 0.0282(5) Uani 1 1 d . . . . .
H5 H 0.8548 -0.4456 -0.1270 0.034 Uiso 1 1 calc R U . . .
C6 C 0.73754(14) -0.3857(6) -0.17586(12) 0.0297(6) Uani 1 1 d . . . . .
H6 H 0.7268 -0.4996 -0.2204 0.036 Uiso 1 1 calc R U . . .
C7 C 0.67535(13) -0.2514(6) -0.16647(12) 0.0297(6) Uani 1 1 d . . . . .
H7 H 0.6228 -0.2801 -0.2045 0.036 Uiso 1 1 calc R U . . .
C8 C 0.68931(13) -0.0807(6) -0.10364(11) 0.0255(5) Uani 1 1 d . . . . .
H8 H 0.6463 0.0068 -0.0988 0.031 Uiso 1 1 calc R U . . .
C8A C 0.76779(12) -0.0316(6) -0.04488(11) 0.0236(5) Uani 1 1 d . . . . .
C9 C 0.78389(12) 0.1417(6) 0.02140(11) 0.0228(5) Uani 1 1 d . . . . .
C9A C 0.86315(12) 0.1737(6) 0.07899(11) 0.0238(5) Uani 1 1 d . . . . .
C10 C 0.90760(13) -0.1444(6) 0.00326(12) 0.0255(5) Uani 1 1 d . . . . .
H10 H 0.9491 -0.2434 -0.0024 0.031 Uiso 1 1 calc R U . . .
C10A C 0.83052(13) -0.1757(6) -0.05392(12) 0.0250(5) Uani 1 1 d . . . . .
C11 C 0.71788(12) 0.3024(6) 0.02514(12) 0.0249(5) Uani 1 1 d . . . . .
H11 H 0.6802 0.3993 -0.0201 0.030 Uiso 1 1 calc R U . . .
C12 C 0.70213(12) 0.3347(6) 0.08282(11) 0.0255(5) Uani 1 1 d . . . . .
H12 H 0.7354 0.2357 0.1295 0.031 Uiso 1 1 calc R U . . .
C13 C 0.63482(12) 0.5193(6) 0.07297(12) 0.0256(5) Uani 1 1 d . . . . .
H13 H 0.6042 0.6165 0.0255 0.031 Uiso 1 1 calc R U . . .
C14 C 0.61040(12) 0.5696(6) 0.12456(12) 0.0265(5) Uani 1 1 d . . . . .
C15 C 0.65056(13) 0.4322(6) 0.19838(13) 0.0281(5) Uani 1 1 d . . . . .
N16 N 0.68248(12) 0.3174(6) 0.25699(11) 0.0376(5) Uani 1 1 d . . . . .
C17 C 0.54086(13) 0.7611(6) 0.10678(12) 0.0300(6) Uani 1 1 d . . . . .
N18 N 0.48513(12) 0.9144(6) 0.09115(11) 0.0398(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
C1 C2 1.371(3) . ?
C1 C9A 1.429(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.413(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.348(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.432(3) . ?
C4 H4 0.9500 . ?
C4A C10 1.400(3) . ?
C4A C9A 1.437(3) . ?
C5 C6 1.365(3) . ?
C5 C10A 1.433(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.367(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.435(3) . ?
C8 H8 0.9500 . ?
C8A C9 1.422(3) . ?
C8A C10A 1.433(3) . ?
C9 C9A 1.429(3) . ?
C9 C11 1.465(3) . ?
C10 C10A 1.397(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.352(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.430(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.355(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.441(3) . ?
C14 C17 1.442(3) . ?
C15 N16 1.153(3) . ?
C17 N18 1.151(3) . ?

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 C9A 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
C9A C1 H1 119.5 . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C4A C4 H4 119.6 . . ?
C10 C4A C4 120.8(2) . . ?
C10 C4A C9A 119.99(19) . . ?
C4 C4A C9A 119.2(2) . . ?
C6 C5 C10A 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C10A C5 H5 119.6 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C8A 121.1(2) . . ?
C7 C8 H8 119.4 . . ?
C8A C8 H8 119.4 . . ?
C9 C8A C10A 120.34(19) . . ?
C9 C8A C8 122.3(2) . . ?
C10A C8A C8 117.3(2) . . ?
C8A C9 C9A 119.7(2) . . ?
C8A C9 C11 117.67(18) . . ?
C9A C9 C11 122.48(19) . . ?
C9 C9A C1 123.2(2) . . ?
C9 C9A C4A 119.1(2) . . ?
C1 C9A C4A 117.57(19) . . ?
C10A C10 C4A 121.7(2) . . ?
C10A C10 H10 119.2 . . ?
C4A C10 H10 119.2 . . ?
C10 C10A C8A 119.2(2) . . ?
C10 C10A C5 121.2(2) . . ?
C8A C10A C5 119.60(19) . . ?
C12 C11 C9 130.2(2) . . ?
C12 C11 H11 114.9 . . ?
C9 C11 H11 114.9 . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 126.5(2) . . ?
C14 C13 H13 116.7 . . ?
C12 C13 H13 116.7 . . ?
C13 C14 C15 122.6(2) . . ?
C13 C14 C17 120.6(2) . . ?
C15 C14 C17 116.8(2) . . ?
N16 C15 C14 178.9(3) . . ?
N18 C17 C14 178.6(2) . . ?

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
C9A C1 C2 C3 1.2(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C4A 0.1(4) . . . . ?
C3 C4 C4A C10 178.1(2) . . . . ?
C3 C4 C4A C9A -1.1(3) . . . . ?
C10A C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 C8 1.3(4) . . . . ?
C6 C7 C8 C8A 0.1(3) . . . . ?
C7 C8 C8A C9 -179.3(2) . . . . ?
C7 C8 C8A C10A -1.6(3) . . . . ?
C10A C8A C9 C9A 0.4(3) . . . . ?
C8 C8A C9 C9A 178.0(2) . . . . ?
C10A C8A C9 C11 175.9(2) . . . . ?
C8 C8A C9 C11 -6.5(3) . . . . ?
C8A C9 C9A C1 176.0(2) . . . . ?
C11 C9 C9A C1 0.7(3) . . . . ?
C8A C9 C9A C4A 0.0(3) . . . . ?
C11 C9 C9A C4A -175.3(2) . . . . ?
C2 C1 C9A C9 -178.2(2) . . . . ?
C2 C1 C9A C4A -2.1(3) . . . . ?
C10 C4A C9A C9 -0.9(3) . . . . ?
C4 C4A C9A C9 178.3(2) . . . . ?
C10 C4A C9A C1 -177.2(2) . . . . ?
C4 C4A C9A C1 2.0(3) . . . . ?
C4 C4A C10 C10A -177.7(2) . . . . ?
C9A C4A C10 C10A 1.5(3) . . . . ?
C4A C10 C10A C8A -1.1(3) . . . . ?
C4A C10 C10A C5 179.5(2) . . . . ?
C9 C8A C10A C10 0.1(3) . . . . ?
C8 C8A C10A C10 -177.6(2) . . . . ?
C9 C8A C10A C5 179.5(2) . . . . ?
C8 C8A C10A C5 1.8(3) . . . . ?
C6 C5 C10A C10 178.9(2) . . . . ?
C6 C5 C10A C8A -0.5(3) . . . . ?
C8A C9 C11 C12 142.4(2) . . . . ?
C9A C9 C11 C12 -42.2(4) . . . . ?
C9 C11 C12 C13 176.9(2) . . . . ?
C11 C12 C13 C14 178.8(2) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C12 C13 C14 C17 -179.8(2) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4



