# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 973196'
_audit_update_record             
;
2013-11-22 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N5'
_chemical_formula_weight         249.28

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                   11.781(4)
_cell_length_b                   8.473(3)
_cell_length_c                   24.554(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.214(6)
_cell_angle_gamma                90.00
_cell_volume                     2450.5(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2206
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      28.02

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_process_details   SADABS

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7356
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28.43
_reflns_number_total             2992
_reflns_number_gt                2019
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0738P)²+0.7598P] 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       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.007

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
C1 C 0.72910(16) -0.1866(2) 0.26849(7) 0.0637(5) Uani 1 1 d . . .
H1 H 0.7511 -0.1586 0.2336 0.076 Uiso 1 1 calc R . .
C2 C 0.65310(15) -0.3086(2) 0.27314(7) 0.0604(4) Uani 1 1 d . . .
H2 H 0.6255 -0.3618 0.2425 0.072 Uiso 1 1 calc R . .
C3 C 0.61936(15) -0.3493(2) 0.32410(7) 0.0593(4) Uani 1 1 d . . .
H3 H 0.5670 -0.4301 0.3289 0.071 Uiso 1 1 calc R . .
C4 C 0.66414(13) -0.26886(18) 0.36831(6) 0.0530(4) Uani 1 1 d . . .
H4 H 0.6432 -0.2953 0.4035 0.064 Uiso 1 1 calc R . .
C5 C 0.74044(12) -0.14859(16) 0.35968(5) 0.0439(3) Uani 1 1 d . . .
C6 C 0.78881(11) -0.05680(16) 0.40568(5) 0.0428(3) Uani 1 1 d . . .
C7 C 0.86838(11) 0.10583(16) 0.48645(5) 0.0419(3) Uani 1 1 d . . .
C8 C 0.91294(11) 0.20022(16) 0.53226(5) 0.0414(3) Uani 1 1 d . . .
C9 C 0.86335(13) 0.19285(18) 0.58305(6) 0.0515(4) Uani 1 1 d . . .
H9 H 0.8008 0.1280 0.5882 0.062 Uiso 1 1 calc R . .
C10 C 0.90654(15) 0.2813(2) 0.62571(6) 0.0579(4) Uani 1 1 d . . .
H10 H 0.8723 0.2752 0.6594 0.069 Uiso 1 1 calc R . .
C11 C 0.99943(13) 0.37908(18) 0.61974(6) 0.0511(4) Uani 1 1 d . . .
C12 C 1.04756(13) 0.38607(19) 0.56907(6) 0.0546(4) Uani 1 1 d . . .
H12 H 1.1099 0.4512 0.5639 0.066 Uiso 1 1 calc R . .
C13 C 1.00543(12) 0.29895(18) 0.52600(6) 0.0495(4) Uani 1 1 d . . .
H13 H 1.0394 0.3064 0.4923 0.059 Uiso 1 1 calc R . .
C14 C 1.04767(17) 0.4735(2) 0.66660(8) 0.0710(5) Uani 1 1 d . . .
H14A H 1.1093 0.4164 0.6835 0.106 Uiso 1 1 calc R . .
H14B H 0.9897 0.4913 0.6928 0.106 Uiso 1 1 calc R . .
H14C H 1.0748 0.5730 0.6535 0.106 Uiso 1 1 calc R . .
N1 N 0.77347(12) -0.10581(16) 0.31010(5) 0.0568(4) Uani 1 1 d . . .
N2 N 0.74324(11) -0.07842(15) 0.45449(5) 0.0501(3) Uani 1 1 d . . .
N3 N 0.78384(10) 0.00402(15) 0.49597(5) 0.0497(3) Uani 1 1 d . . .
N4 N 0.91573(11) 0.12501(16) 0.43772(5) 0.0560(4) Uani 1 1 d . . .
N5 N 0.87519(11) 0.04115(17) 0.39621(5) 0.0565(4) 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 N1 1.328(2) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.3360(18) . ?
C5 C6 1.476(2) . ?
C6 N2 1.3363(17) . ?
C6 N5 1.3372(19) . ?
C7 N4 1.3407(17) . ?
C7 N3 1.3419(18) . ?
C7 C8 1.468(2) . ?
C8 C13 1.385(2) . ?
C8 C9 1.3896(19) . ?
C9 C10 1.377(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(2) . ?
C11 C14 1.503(2) . ?
C12 C13 1.374(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 N3 1.3165(17) . ?
N4 N5 1.3234(18) . ?

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 C1 C2 124.79(15) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C1 118.00(15) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 118.88(16) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.01(14) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.98(14) . . ?
N1 C5 C6 116.05(13) . . ?
C4 C5 C6 120.97(12) . . ?
N2 C6 N5 124.24(13) . . ?
N2 C6 C5 117.27(13) . . ?
N5 C6 C5 118.49(12) . . ?
N4 C7 N3 123.90(13) . . ?
N4 C7 C8 117.96(12) . . ?
N3 C7 C8 118.13(12) . . ?
C13 C8 C9 118.26(13) . . ?
C13 C8 C7 120.90(12) . . ?
C9 C8 C7 120.85(13) . . ?
C10 C9 C8 120.18(14) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.74(14) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 117.56(14) . . ?
C12 C11 C14 120.78(16) . . ?
C10 C11 C14 121.66(15) . . ?
C13 C12 C11 121.50(15) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C8 120.76(14) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C5 116.34(14) . . ?
N3 N2 C6 118.34(12) . . ?
N2 N3 C7 117.73(12) . . ?
N5 N4 C7 118.17(12) . . ?
N4 N5 C6 117.57(12) . . ?

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
N1 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 N1 0.0(2) . . . . ?
C3 C4 C5 C6 178.69(13) . . . . ?
N1 C5 C6 N2 168.89(13) . . . . ?
C4 C5 C6 N2 -9.9(2) . . . . ?
N1 C5 C6 N5 -11.56(19) . . . . ?
C4 C5 C6 N5 169.65(13) . . . . ?
N4 C7 C8 C13 -3.77(19) . . . . ?
N3 C7 C8 C13 175.32(12) . . . . ?
N4 C7 C8 C9 176.21(13) . . . . ?
N3 C7 C8 C9 -4.7(2) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
C7 C8 C9 C10 179.59(13) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C9 C10 C11 C14 -178.94(15) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C14 C11 C12 C13 179.12(14) . . . . ?
C11 C12 C13 C8 -0.3(2) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
C7 C8 C13 C12 -179.42(13) . . . . ?
C2 C1 N1 C5 0.0(3) . . . . ?
C4 C5 N1 C1 -0.4(2) . . . . ?
C6 C5 N1 C1 -179.15(13) . . . . ?
N5 C6 N2 N3 1.5(2) . . . . ?
C5 C6 N2 N3 -178.96(12) . . . . ?
C6 N2 N3 C7 0.4(2) . . . . ?
N4 C7 N3 N2 -2.0(2) . . . . ?
C8 C7 N3 N2 179.00(11) . . . . ?
N3 C7 N4 N5 1.5(2) . . . . ?
C8 C7 N4 N5 -179.43(12) . . . . ?
C7 N4 N5 C6 0.4(2) . . . . ?
N2 C6 N5 N4 -2.0(2) . . . . ?
C5 C6 N5 N4 178.54(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        28.43
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
