# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_20161123_0m
_database_code_depnum_ccdc_archive 'CCDC 1536706'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N4'
_chemical_formula_weight         276.34

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   P2(1)/n

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                   9.6046(4)
_cell_length_b                   10.6651(5)
_cell_length_c                   14.3071(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.530(3)
_cell_angle_gamma                90.00
_cell_volume                     1440.85(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    7245
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.17

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3579
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         28.33
_reflns_number_total             3579
_reflns_number_gt                2816
_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)+(0.0731P)²+0.3250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3579
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1485
_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
N1 N 0.20222(16) 0.49122(13) -0.04515(10) 0.0522(4) Uani 1 1 d . . .
N2 N 0.32495(14) 0.66501(13) 0.03978(9) 0.0468(3) Uani 1 1 d . . .
N3 N 0.39447(14) 0.86837(13) 0.10424(10) 0.0468(3) Uani 1 1 d . . .
N4 N 0.06497(15) 0.79839(14) -0.04330(10) 0.0526(4) Uani 1 1 d . . .
C1 C 0.21363(17) 0.61338(15) -0.01623(11) 0.0452(4) Uani 1 1 d . . .
C2 C 0.30119(16) 0.78644(15) 0.05183(11) 0.0434(4) Uani 1 1 d . . .
C3 C 0.33007(18) 0.98628(15) 0.10008(12) 0.0462(4) Uani 1 1 d . . .
C4 C 0.19735(18) 0.97914(16) 0.04585(13) 0.0519(4) Uani 1 1 d . . .
H4B H 0.1328 1.0446 0.0328 0.062 Uiso 1 1 calc R . .
C5 C 0.17597(17) 0.85358(16) 0.01301(12) 0.0471(4) Uani 1 1 d . . .
C6 C 0.08605(18) 0.67630(16) -0.05790(11) 0.0480(4) Uani 1 1 d . . .
C7 C -0.0012(2) 0.58449(18) -0.11246(12) 0.0562(4) Uani 1 1 d . . .
H7A H -0.0913 0.5970 -0.1480 0.067 Uiso 1 1 calc R . .
C8 C 0.0720(2) 0.47603(18) -0.10276(13) 0.0566(5) Uani 1 1 d . . .
H8A H 0.0388 0.4007 -0.1313 0.068 Uiso 1 1 calc R . .
C9 C 0.3064(3) 0.3948(2) -0.0153(2) 0.0742(6) Uani 1 1 d . . .
H9A H 0.261(3) 0.312(3) -0.033(2) 0.111 Uiso 1 1 d . . .
H9B H 0.339(3) 0.393(3) 0.052(2) 0.111 Uiso 1 1 d . . .
H9C H 0.385(3) 0.402(3) -0.046(2) 0.111 Uiso 1 1 d . . .
C10 C 0.5328(2) 0.8326(2) 0.15560(17) 0.0648(5) Uani 1 1 d . . .
H10A H 0.566(3) 0.892(3) 0.2112(19) 0.097 Uiso 1 1 d . . .
H10B H 0.607(3) 0.844(2) 0.1112(18) 0.097 Uiso 1 1 d . . .
H10C H 0.528(3) 0.749(3) 0.171(2) 0.097 Uiso 1 1 d . . .
C11 C 0.39892(17) 1.09755(16) 0.14861(11) 0.0464(4) Uani 1 1 d . . .
C12 C 0.53635(19) 1.13353(18) 0.14238(12) 0.0537(4) Uani 1 1 d . . .
H12A H 0.5902 1.0830 0.1097 0.064 Uiso 1 1 calc R . .
C13 C 0.5937(2) 1.24326(18) 0.18405(13) 0.0583(5) Uani 1 1 d . . .
H13A H 0.6858 1.2650 0.1791 0.070 Uiso 1 1 calc R . .
C14 C 0.5169(2) 1.32186(17) 0.23314(12) 0.0550(4) Uani 1 1 d . . .
C15 C 0.3810(2) 1.28481(17) 0.24045(13) 0.0559(4) Uani 1 1 d . . .
H15A H 0.3279 1.3348 0.2740 0.067 Uiso 1 1 calc R . .
C16 C 0.32267(18) 1.17548(17) 0.19907(12) 0.0522(4) Uani 1 1 d . . .
H16A H 0.2310 1.1534 0.2049 0.063 Uiso 1 1 calc R . .
C17 C 0.5772(3) 1.4444(2) 0.27506(19) 0.0839(7) Uani 1 1 d . . .
H17A H 0.5090 1.4855 0.3060 0.126 Uiso 1 1 calc R . .
H17B H 0.5990 1.4972 0.2253 0.126 Uiso 1 1 calc R . .
H17C H 0.6620 1.4286 0.3206 0.126 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 C1 1.365(2) . ?
N1 C8 1.376(2) . ?
N1 C9 1.445(3) . ?
N2 C2 1.332(2) . ?
N2 C1 1.332(2) . ?
N3 C2 1.372(2) . ?
N3 C3 1.398(2) . ?
N3 C10 1.447(2) . ?
N4 C6 1.340(2) . ?
N4 C5 1.348(2) . ?
C1 C6 1.428(2) . ?
C2 C5 1.422(2) . ?
C3 C4 1.368(2) . ?
C3 C11 1.470(2) . ?
C4 C5 1.422(2) . ?
C4 H4B 0.9300 . ?
C6 C7 1.425(2) . ?
C7 C8 1.347(3) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 H9A 1.00(3) . ?
C9 H9B 0.96(3) . ?
C9 H9C 0.94(3) . ?
C10 H10A 1.02(3) . ?
C10 H10B 1.05(3) . ?
C10 H10C 0.92(3) . ?
C11 C12 1.393(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.381(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.386(3) . ?
C14 C17 1.509(3) . ?
C15 C16 1.379(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C1 N1 C8 107.92(15) . . ?
C1 N1 C9 125.25(16) . . ?
C8 N1 C9 126.74(17) . . ?
C2 N2 C1 110.00(13) . . ?
C2 N3 C3 108.06(13) . . ?
C2 N3 C10 123.86(15) . . ?
C3 N3 C10 128.07(15) . . ?
C6 N4 C5 113.07(14) . . ?
N2 C1 N1 125.99(15) . . ?
N2 C1 C6 126.14(15) . . ?
N1 C1 C6 107.86(15) . . ?
N2 C2 N3 125.44(14) . . ?
N2 C2 C5 126.27(15) . . ?
N3 C2 C5 108.29(14) . . ?
C4 C3 N3 109.47(14) . . ?
C4 C3 C11 127.24(15) . . ?
N3 C3 C11 123.30(14) . . ?
C3 C4 C5 107.65(15) . . ?
C3 C4 H4B 126.2 . . ?
C5 C4 H4B 126.2 . . ?
N4 C5 C4 131.25(15) . . ?
N4 C5 C2 122.23(15) . . ?
C4 C5 C2 106.52(14) . . ?
N4 C6 C7 131.50(16) . . ?
N4 C6 C1 122.28(15) . . ?
C7 C6 C1 106.22(15) . . ?
C8 C7 C6 106.88(16) . . ?
C8 C7 H7A 126.6 . . ?
C6 C7 H7A 126.6 . . ?
C7 C8 N1 111.12(16) . . ?
C7 C8 H8A 124.4 . . ?
N1 C8 H8A 124.4 . . ?
N1 C9 H9A 108.2(18) . . ?
N1 C9 H9B 113.0(18) . . ?
H9A C9 H9B 106(2) . . ?
N1 C9 H9C 111.7(18) . . ?
H9A C9 H9C 108(2) . . ?
H9B C9 H9C 110(2) . . ?
N3 C10 H10A 111.0(14) . . ?
N3 C10 H10B 109.1(14) . . ?
H10A C10 H10B 105(2) . . ?
N3 C10 H10C 107.1(18) . . ?
H10A C10 H10C 116(2) . . ?
H10B C10 H10C 109(2) . . ?
C12 C11 C16 117.56(16) . . ?
C12 C11 C3 122.82(15) . . ?
C16 C11 C3 119.51(15) . . ?
C13 C12 C11 120.89(17) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C14 121.54(17) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C15 C14 C13 117.42(17) . . ?
C15 C14 C17 121.03(19) . . ?
C13 C14 C17 121.54(19) . . ?
C16 C15 C14 121.53(17) . . ?
C16 C15 H15A 119.2 . . ?
C14 C15 H15A 119.2 . . ?
C15 C16 C11 121.05(16) . . ?
C15 C16 H16A 119.5 . . ?
C11 C16 H16A 119.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C2 N2 C1 N1 178.68(15) . . . . ?
C2 N2 C1 C6 -0.3(2) . . . . ?
C8 N1 C1 N2 -179.43(15) . . . . ?
C9 N1 C1 N2 3.8(3) . . . . ?
C8 N1 C1 C6 -0.33(18) . . . . ?
C9 N1 C1 C6 -177.12(19) . . . . ?
C1 N2 C2 N3 -179.00(14) . . . . ?
C1 N2 C2 C5 1.0(2) . . . . ?
C3 N3 C2 N2 -179.51(15) . . . . ?
C10 N3 C2 N2 -1.0(3) . . . . ?
C3 N3 C2 C5 0.53(18) . . . . ?
C10 N3 C2 C5 179.01(18) . . . . ?
C2 N3 C3 C4 0.15(19) . . . . ?
C10 N3 C3 C4 -178.25(19) . . . . ?
C2 N3 C3 C11 179.69(14) . . . . ?
C10 N3 C3 C11 1.3(3) . . . . ?
N3 C3 C4 C5 -0.8(2) . . . . ?
C11 C3 C4 C5 179.72(16) . . . . ?
C6 N4 C5 C4 -179.96(18) . . . . ?
C6 N4 C5 C2 0.0(2) . . . . ?
C3 C4 C5 N4 -178.97(17) . . . . ?
C3 C4 C5 C2 1.06(19) . . . . ?
N2 C2 C5 N4 -0.9(3) . . . . ?
N3 C2 C5 N4 179.05(15) . . . . ?
N2 C2 C5 C4 179.06(16) . . . . ?
N3 C2 C5 C4 -0.98(18) . . . . ?
C5 N4 C6 C7 -179.27(17) . . . . ?
C5 N4 C6 C1 0.6(2) . . . . ?
N2 C1 C6 N4 -0.6(3) . . . . ?
N1 C1 C6 N4 -179.66(15) . . . . ?
N2 C1 C6 C7 179.37(15) . . . . ?
N1 C1 C6 C7 0.27(18) . . . . ?
N4 C6 C7 C8 179.81(18) . . . . ?
C1 C6 C7 C8 -0.11(19) . . . . ?
C6 C7 C8 N1 -0.1(2) . . . . ?
C1 N1 C8 C7 0.3(2) . . . . ?
C9 N1 C8 C7 177.0(2) . . . . ?
C4 C3 C11 C12 -131.89(19) . . . . ?
N3 C3 C11 C12 48.6(2) . . . . ?
C4 C3 C11 C16 44.5(2) . . . . ?
N3 C3 C11 C16 -135.01(17) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
C3 C11 C12 C13 175.74(16) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C12 C13 C14 C17 -177.34(19) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C17 C14 C15 C16 177.31(19) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
C3 C11 C16 C15 -175.91(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054
