# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1440718'
_audit_update_record             
;
2015-12-06 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 N5'
_chemical_formula_sum            'C18 H12 N5'
_chemical_formula_weight         298.33

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   C2/c

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

_cell_length_a                   14.200(8)
_cell_length_b                   19.440(8)
_cell_length_c                   13.057(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.10(4)
_cell_angle_gamma                90.00
_cell_volume                     3086(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2841
_cell_measurement_theta_min      5.543
_cell_measurement_theta_max      53.466

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_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  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12450
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         28.70
_reflns_number_total             3835
_reflns_number_gt                2245
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1290P)²+0.9490P] 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     SHELXL
_refine_ls_extinction_coef       0.0108(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3835
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2388
_refine_ls_wR_factor_gt          0.1932
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.87502(15) 0.40530(9) 0.24847(16) 0.0485(5) Uani 1 1 d . . .
N2 N 0.89979(18) 0.33809(10) 0.28841(19) 0.0593(6) Uani 1 1 d . . .
N3 N 0.97228(15) 0.41356(10) 0.44356(16) 0.0517(5) Uani 1 1 d . . .
N4 N 0.90628(15) 0.51785(9) 0.32707(15) 0.0482(5) Uani 1 1 d . . .
N5 N 0.7111(2) 0.54570(16) -0.09983(19) 0.0922(9) Uani 1 1 d . . .
C1 C 0.4828(4) 0.3471(4) -0.0516(5) 0.197(4) Uani 1 1 d . . .
H1 H 0.4106 0.3314 -0.0912 0.237 Uiso 1 1 calc R . .
C2 C 0.5181(3) 0.3934(2) 0.0434(5) 0.139(2) Uani 1 1 d . . .
H12 H 0.4706 0.4077 0.0684 0.167 Uiso 1 1 calc R . .
C3 C 0.6246(2) 0.41740(17) 0.0993(3) 0.0836(9) Uani 1 1 d . . .
H11 H 0.6492 0.4486 0.1620 0.100 Uiso 1 1 calc R . .
C4 C 0.6944(2) 0.39539(13) 0.06289(19) 0.0604(7) Uani 1 1 d . . .
C5 C 0.80990(19) 0.42333(12) 0.12242(19) 0.0510(6) Uani 1 1 d . . .
H8 H 0.8459 0.4045 0.0816 0.061 Uiso 1 1 calc R . .
C6 C 0.81154(18) 0.50186(12) 0.11647(18) 0.0470(5) Uani 1 1 d . . .
C7 C 0.85442(15) 0.54445(11) 0.21253(16) 0.0421(5) Uani 1 1 d . . .
C8 C 0.84793(16) 0.62084(11) 0.20652(17) 0.0448(5) Uani 1 1 d . . .
C9 C 0.87044(18) 0.65782(12) 0.13063(19) 0.0533(6) Uani 1 1 d . . .
H3 H 0.8890 0.6349 0.0810 0.064 Uiso 1 1 calc R . .
C10 C 0.8653(2) 0.72914(14) 0.1291(2) 0.0667(7) Uani 1 1 d . . .
H4 H 0.8808 0.7537 0.0784 0.080 Uiso 1 1 calc R . .
C11 C 0.8378(2) 0.76363(14) 0.2006(2) 0.0749(9) Uani 1 1 d . . .
H2 H 0.8342 0.8114 0.1984 0.090 Uiso 1 1 calc R . .
C12 C 0.9576(2) 0.34695(12) 0.4046(2) 0.0579(6) Uani 1 1 d . . .
H7 H 0.9870 0.3101 0.4574 0.069 Uiso 1 1 calc R . .
C13 C 0.91800(16) 0.44795(11) 0.34184(17) 0.0442(5) Uani 1 1 d . . .
C14 C 0.8209(2) 0.65631(13) 0.2804(2) 0.0564(6) Uani 1 1 d . . .
H6 H 0.8066 0.6323 0.3324 0.068 Uiso 1 1 calc R . .
C15 C 0.8155(2) 0.72745(14) 0.2762(2) 0.0720(8) Uani 1 1 d . . .
H5 H 0.7965 0.7510 0.3250 0.086 Uiso 1 1 calc R . .
C16 C 0.7555(2) 0.52853(13) -0.0026(2) 0.0590(6) Uani 1 1 d . . .
C17 C 0.6587(4) 0.3484(2) -0.0294(3) 0.1241(19) Uani 1 1 d . . .
H10 H 0.7067 0.3328 -0.0527 0.149 Uiso 1 1 calc R . .
C18 C 0.5519(7) 0.3247(3) -0.0869(4) 0.185(4) Uani 1 1 d . . .
H9 H 0.5275 0.2935 -0.1496 0.222 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 C13 1.333(3) . ?
N1 N2 1.383(3) . ?
N1 C5 1.454(3) . ?
N2 C12 1.311(3) . ?
N3 C13 1.322(3) . ?
N3 C12 1.367(3) . ?
N4 C13 1.370(3) . ?
N4 C7 1.382(3) . ?
N5 C16 1.137(3) . ?
C1 C18 1.353(11) . ?
C1 C2 1.400(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(5) . ?
C2 H12 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H11 0.9300 . ?
C4 C17 1.383(4) . ?
C4 C5 1.508(3) . ?
C5 C6 1.529(3) . ?
C5 H8 0.9800 . ?
C6 C7 1.357(3) . ?
C6 C16 1.429(3) . ?
C7 C8 1.487(3) . ?
C8 C9 1.389(3) . ?
C8 C14 1.391(3) . ?
C9 C10 1.388(3) . ?
C9 H3 0.9300 . ?
C10 C11 1.360(4) . ?
C10 H4 0.9300 . ?
C11 C15 1.377(4) . ?
C11 H2 0.9300 . ?
C12 H7 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H6 0.9300 . ?
C15 H5 0.9300 . ?
C17 C18 1.378(8) . ?
C17 H10 0.9300 . ?
C18 H9 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
C13 N1 N2 109.61(18) . . ?
C13 N1 C5 127.45(19) . . ?
N2 N1 C5 122.93(18) . . ?
C12 N2 N1 101.39(19) . . ?
C13 N3 C12 101.99(18) . . ?
C13 N4 C7 118.79(17) . . ?
C18 C1 C2 121.2(4) . . ?
C18 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 118.7(5) . . ?
C3 C2 H12 120.7 . . ?
C1 C2 H12 120.7 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H11 119.9 . . ?
C2 C3 H11 119.9 . . ?
C3 C4 C17 120.2(3) . . ?
C3 C4 C5 119.9(2) . . ?
C17 C4 C5 119.9(3) . . ?
N1 C5 C4 112.52(18) . . ?
N1 C5 C6 106.30(17) . . ?
C4 C5 C6 112.0(2) . . ?
N1 C5 H8 108.6 . . ?
C4 C5 H8 108.6 . . ?
C6 C5 H8 108.6 . . ?
C7 C6 C16 121.1(2) . . ?
C7 C6 C5 125.01(19) . . ?
C16 C6 C5 113.77(19) . . ?
C6 C7 N4 120.4(2) . . ?
C6 C7 C8 125.07(18) . . ?
N4 C7 C8 114.50(17) . . ?
C9 C8 C14 119.0(2) . . ?
C9 C8 C7 121.6(2) . . ?
C14 C8 C7 119.36(19) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H3 120.1 . . ?
C8 C9 H3 120.1 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H4 119.5 . . ?
C9 C10 H4 119.5 . . ?
C10 C11 C15 119.7(3) . . ?
C10 C11 H2 120.2 . . ?
C15 C11 H2 120.2 . . ?
N2 C12 N3 116.0(2) . . ?
N2 C12 H7 122.0 . . ?
N3 C12 H7 122.0 . . ?
N3 C13 N1 110.98(19) . . ?
N3 C13 N4 127.46(18) . . ?
N1 C13 N4 121.54(18) . . ?
C15 C14 C8 119.9(2) . . ?
C15 C14 H6 120.1 . . ?
C8 C14 H6 120.1 . . ?
C11 C15 C14 120.6(3) . . ?
C11 C15 H5 119.7 . . ?
C14 C15 H5 119.7 . . ?
N5 C16 C6 175.7(3) . . ?
C18 C17 C4 120.0(5) . . ?
C18 C17 H10 120.0 . . ?
C4 C17 H10 120.0 . . ?
C1 C18 C17 119.6(5) . . ?
C1 C18 H9 120.2 . . ?
C17 C18 H9 120.2 . . ?

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
C13 N1 N2 C12 -0.7(2) . . . . ?
C5 N1 N2 C12 -179.7(2) . . . . ?
C18 C1 C2 C3 1.5(8) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C17 -0.6(5) . . . . ?
C2 C3 C4 C5 178.4(3) . . . . ?
C13 N1 C5 C4 -116.3(2) . . . . ?
N2 N1 C5 C4 62.6(3) . . . . ?
C13 N1 C5 C6 6.6(3) . . . . ?
N2 N1 C5 C6 -174.50(18) . . . . ?
C3 C4 C5 N1 63.5(3) . . . . ?
C17 C4 C5 N1 -117.4(3) . . . . ?
C3 C4 C5 C6 -56.2(3) . . . . ?
C17 C4 C5 C6 122.9(3) . . . . ?
N1 C5 C6 C7 -7.4(3) . . . . ?
C4 C5 C6 C7 115.8(2) . . . . ?
N1 C5 C6 C16 176.97(19) . . . . ?
C4 C5 C6 C16 -59.8(3) . . . . ?
C16 C6 C7 N4 178.6(2) . . . . ?
C5 C6 C7 N4 3.3(3) . . . . ?
C16 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C8 -174.7(2) . . . . ?
C13 N4 C7 C6 3.0(3) . . . . ?
C13 N4 C7 C8 -178.85(18) . . . . ?
C6 C7 C8 C9 -45.8(3) . . . . ?
N4 C7 C8 C9 136.1(2) . . . . ?
C6 C7 C8 C14 135.5(2) . . . . ?
N4 C7 C8 C14 -42.5(3) . . . . ?
C14 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 -178.9(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C15 0.4(4) . . . . ?
N1 N2 C12 N3 0.2(3) . . . . ?
C13 N3 C12 N2 0.3(3) . . . . ?
C12 N3 C13 N1 -0.7(2) . . . . ?
C12 N3 C13 N4 -179.2(2) . . . . ?
N2 N1 C13 N3 0.9(2) . . . . ?
C5 N1 C13 N3 179.9(2) . . . . ?
N2 N1 C13 N4 179.45(18) . . . . ?
C5 N1 C13 N4 -1.6(3) . . . . ?
C7 N4 C13 N3 174.3(2) . . . . ?
C7 N4 C13 N1 -4.0(3) . . . . ?
C9 C8 C14 C15 0.8(3) . . . . ?
C7 C8 C14 C15 179.5(2) . . . . ?
C10 C11 C15 C14 0.2(4) . . . . ?
C8 C14 C15 C11 -0.8(4) . . . . ?
C7 C6 C16 N5 168(4) . . . . ?
C5 C6 C16 N5 -16(4) . . . . ?
C3 C4 C17 C18 1.4(5) . . . . ?
C5 C4 C17 C18 -177.6(4) . . . . ?
C2 C1 C18 C17 -0.7(9) . . . . ?
C4 C17 C18 C1 -0.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.150
