# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1405923'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N4'
_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_weight         248.29

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.7080(4)
_cell_length_b                   15.9311(9)
_cell_length_c                   9.5590(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.714(4)
_cell_angle_gamma                90
_cell_volume                     1232.00(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    10076
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.084
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.108
1 0 0 0.120
-1 0 1 0.136
1 0 -1 0.130
0 -1 0 0.066
0 1 0 0.049
1 -1 0 0.119
-1 1 0 0.093
-1 1 -1 0.131
0 0 -1 0.154


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10026
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2795
_reflns_number_gt                2267
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0332P)²+0.7337P] 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         2795
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
N4 N 0.59760(16) 0.07684(8) 0.25833(15) 0.0229(3) Uani 1 1 d . . .
N1 N 0.97517(15) 0.25765(8) 0.43942(14) 0.0189(3) Uani 1 1 d . . .
N3 N 1.42023(15) 0.19303(8) 0.79324(14) 0.0222(3) Uani 1 1 d . . .
C4 C 0.78364(19) 0.46322(9) 0.30023(17) 0.0214(3) Uani 1 1 d . . .
H4 H 0.6812 0.4890 0.2758 0.026 Uiso 1 1 d R . .
C13 C 0.6964(2) 0.07803(10) 0.40406(18) 0.0223(3) Uani 1 1 d . . .
H13 H 0.6792 0.0373 0.4665 0.027 Uiso 1 1 d R . .
C2 C 1.08185(18) 0.38798(9) 0.37725(16) 0.0186(3) Uani 1 1 d . . .
H2 H 1.1865 0.3644 0.4039 0.022 Uiso 1 1 d R . .
C12 C 0.82146(18) 0.13537(9) 0.46826(16) 0.0193(3) Uani 1 1 d . . .
H12 H 0.8861 0.1326 0.5704 0.023 Uiso 1 1 d R . .
C10 C 1.19756(18) 0.29022(9) 0.67788(17) 0.0193(3) Uani 1 1 d . . .
H10 H 1.1493 0.3417 0.6825 0.023 Uiso 1 1 d R . .
C1 C 0.95166(18) 0.34183(9) 0.38861(16) 0.0167(3) Uani 1 1 d . . .
C9 C 1.34459(18) 0.26633(10) 0.78986(17) 0.0205(3) Uani 1 1 d . . .
H9 H 1.3941 0.3038 0.8682 0.025 Uiso 1 1 d R . .
C6 C 1.12376(17) 0.23542(9) 0.55864(16) 0.0171(3) Uani 1 1 d . . .
N2 N 0.90660(17) 0.50840(8) 0.28544(15) 0.0237(3) Uani 1 1 d . . .
C5 C 0.79849(18) 0.38098(9) 0.34930(16) 0.0191(3) Uani 1 1 d . . .
H5 H 0.7083 0.3524 0.3560 0.023 Uiso 1 1 d R . .
C15 C 0.74853(18) 0.19697(10) 0.22567(17) 0.0205(3) Uani 1 1 d . . .
H15 H 0.7630 0.2369 0.1606 0.025 Uiso 1 1 d R . .
C11 C 0.84950(17) 0.19721(9) 0.37777(16) 0.0173(3) Uani 1 1 d . . .
C8 C 1.34587(19) 0.14081(10) 0.67814(18) 0.0225(3) Uani 1 1 d . . .
H8 H 1.3955 0.0891 0.6782 0.027 Uiso 1 1 d R . .
C14 C 0.62647(19) 0.13655(10) 0.17279(17) 0.0224(3) Uani 1 1 d . . .
H14 H 0.5602 0.1375 0.0710 0.027 Uiso 1 1 d R . .
C3 C 1.05266(19) 0.46979(10) 0.32541(17) 0.0213(3) Uani 1 1 d . . .
H3 H 1.1408 0.5000 0.3179 0.026 Uiso 1 1 d R . .
C7 C 1.20004(18) 0.15849(10) 0.55914(17) 0.0206(3) Uani 1 1 d . . .
H7 H 1.1541 0.1201 0.4816 0.025 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N4 0.0212(6) 0.0193(7) 0.0257(7) -0.0024(5) 0.0058(5) -0.0028(5)
N1 0.0177(6) 0.0138(6) 0.0211(6) 0.0026(5) 0.0022(5) -0.0011(5)
N3 0.0171(6) 0.0247(7) 0.0231(7) 0.0037(5) 0.0055(5) 0.0011(5)
C4 0.0204(7) 0.0194(7) 0.0223(8) -0.0001(6) 0.0055(6) 0.0050(6)
C13 0.0258(8) 0.0181(7) 0.0234(8) 0.0011(6) 0.0098(6) -0.0028(6)
C2 0.0171(7) 0.0197(7) 0.0185(7) -0.0010(6) 0.0060(6) 0.0002(6)
C12 0.0211(7) 0.0187(7) 0.0159(7) 0.0005(6) 0.0043(6) -0.0009(6)
C10 0.0194(7) 0.0164(7) 0.0221(7) 0.0010(6) 0.0077(6) 0.0005(6)
C1 0.0189(7) 0.0143(7) 0.0151(6) -0.0005(5) 0.0043(5) -0.0002(5)
C9 0.0194(7) 0.0213(7) 0.0200(7) -0.0009(6) 0.0064(6) -0.0040(6)
C6 0.0152(7) 0.0168(7) 0.0186(7) 0.0027(6) 0.0056(5) -0.0007(5)
N2 0.0299(7) 0.0163(6) 0.0241(7) 0.0002(5) 0.0089(6) 0.0012(5)
C5 0.0170(7) 0.0196(7) 0.0201(7) -0.0007(6) 0.0062(6) -0.0009(6)
C15 0.0224(7) 0.0186(7) 0.0194(7) 0.0021(6) 0.0064(6) -0.0001(6)
C11 0.0168(7) 0.0146(7) 0.0199(7) -0.0015(6) 0.0062(6) 0.0005(5)
C8 0.0203(7) 0.0193(7) 0.0286(8) 0.0015(6) 0.0097(6) 0.0033(6)
C14 0.0212(7) 0.0228(8) 0.0189(7) -0.0015(6) 0.0025(6) 0.0012(6)
C3 0.0240(8) 0.0189(7) 0.0220(7) -0.0011(6) 0.0098(6) -0.0040(6)
C7 0.0198(7) 0.0189(7) 0.0216(7) -0.0014(6) 0.0061(6) -0.0005(6)

_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
N4 C14 1.337(2) . ?
N4 C13 1.339(2) . ?
N1 C11 1.4124(18) . ?
N1 C1 1.4151(18) . ?
N1 C6 1.4168(18) . ?
N3 C9 1.335(2) . ?
N3 C8 1.340(2) . ?
C4 N2 1.340(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9301 . ?
C13 C12 1.380(2) . ?
C13 H13 0.9299 . ?
C2 C3 1.384(2) . ?
C2 C1 1.389(2) . ?
C2 H2 0.9300 . ?
C12 C11 1.391(2) . ?
C12 H12 0.9300 . ?
C10 C9 1.384(2) . ?
C10 C6 1.390(2) . ?
C10 H10 0.9302 . ?
C1 C5 1.392(2) . ?
C9 H9 0.9300 . ?
C6 C7 1.393(2) . ?
N2 C3 1.335(2) . ?
C5 H5 0.9300 . ?
C15 C14 1.384(2) . ?
C15 C11 1.393(2) . ?
C15 H15 0.9300 . ?
C8 C7 1.385(2) . ?
C8 H8 0.9299 . ?
C14 H14 0.9300 . ?
C3 H3 0.9302 . ?
C7 H7 0.9301 . ?

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
C14 N4 C13 115.61(13) . . ?
C11 N1 C1 120.76(12) . . ?
C11 N1 C6 120.08(12) . . ?
C1 N1 C6 119.08(12) . . ?
C9 N3 C8 116.04(13) . . ?
N2 C4 C5 124.54(14) . . ?
N2 C4 H4 117.7 . . ?
C5 C4 H4 117.7 . . ?
N4 C13 C12 124.71(15) . . ?
N4 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
C3 C2 C1 118.65(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C13 C12 C11 118.93(14) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.6 . . ?
C9 C10 C6 118.44(14) . . ?
C9 C10 H10 120.7 . . ?
C6 C10 H10 120.8 . . ?
C2 C1 C5 118.03(13) . . ?
C2 C1 N1 120.66(13) . . ?
C5 C1 N1 121.31(13) . . ?
N3 C9 C10 124.48(14) . . ?
N3 C9 H9 117.7 . . ?
C10 C9 H9 117.8 . . ?
C10 C6 C7 118.32(14) . . ?
C10 C6 N1 120.67(13) . . ?
C7 C6 N1 121.00(13) . . ?
C3 N2 C4 115.85(13) . . ?
C4 C5 C1 118.46(14) . . ?
C4 C5 H5 120.8 . . ?
C1 C5 H5 120.8 . . ?
C14 C15 C11 119.08(14) . . ?
C14 C15 H15 120.4 . . ?
C11 C15 H15 120.5 . . ?
C12 C11 C15 117.31(14) . . ?
C12 C11 N1 120.70(13) . . ?
C15 C11 N1 121.98(13) . . ?
N3 C8 C7 124.48(14) . . ?
N3 C8 H8 117.8 . . ?
C7 C8 H8 117.8 . . ?
N4 C14 C15 124.35(14) . . ?
N4 C14 H14 117.8 . . ?
C15 C14 H14 117.8 . . ?
N2 C3 C2 124.45(14) . . ?
N2 C3 H3 117.7 . . ?
C2 C3 H3 117.8 . . ?
C8 C7 C6 118.23(14) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.8 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
