# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_DLI16_2018
_database_code_depnum_ccdc_archive 'CCDC 1856372'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C16 H14 N4'
_chemical_formula_sum            'C16 H14 N4'
_chemical_formula_weight         262.31

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, 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                   16.3021(12)
_cell_length_b                   8.0165(6)
_cell_length_c                   20.5586(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.284(4)
_cell_angle_gamma                90
_cell_volume                     2614.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3376
_cell_measurement_theta_min      5.01
_cell_measurement_theta_max      30.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9439
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            116902
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.626
_diffrn_reflns_theta_max         34.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5211
_reflns_number_gt                2938
_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-2014/7 (Sheldrick 2014)'
_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)+(0.0519P)²+1.1356P] 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         5211
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
N1 N 0.30493(6) 0.43802(13) 0.40304(5) 0.0273(2) Uani 1 1 d . . . . .
N2 N 0.18057(6) 0.37948(13) 0.42929(5) 0.0251(2) Uani 1 1 d . . . . .
N3 N 0.13320(6) 0.38949(14) 0.47441(5) 0.0281(2) Uani 1 1 d . . . . .
N4 N 0.18564(6) 0.46634(13) 0.52551(5) 0.0251(2) Uani 1 1 d . . . . .
C1 C 0.47536(8) 0.72074(18) 0.64752(6) 0.0364(3) Uani 1 1 d . . . . .
H1 H 0.5225 0.7660 0.6764 0.044 Uiso 1 1 calc R U . . .
C2 C 0.39545(8) 0.76656(17) 0.65283(6) 0.0342(3) Uani 1 1 d . . . . .
H14 H 0.3889 0.8428 0.6853 0.041 Uiso 1 1 calc R U . . .
C3 C 0.32513(8) 0.69938(16) 0.60996(6) 0.0289(3) Uani 1 1 d . . . . .
H11 H 0.2716 0.7325 0.6133 0.035 Uiso 1 1 calc R U . . .
C4 C 0.33380(7) 0.58241(15) 0.56168(6) 0.0246(2) Uani 1 1 d . . . . .
C5 C 0.26293(7) 0.50526(15) 0.51488(5) 0.0240(2) Uani 1 1 d . . . . .
C6 C 0.25996(7) 0.44670(15) 0.44983(6) 0.0245(2) Uani 1 1 d . . . . .
C7 C 0.25057(7) 0.35803(15) 0.35068(6) 0.0265(2) Uani 1 1 d . . . . .
C8 C 0.26387(8) 0.30898(16) 0.28826(6) 0.0317(3) Uani 1 1 d . . . . .
H10 H 0.3142 0.3337 0.2764 0.038 Uiso 1 1 calc R U . . .
C9 C 0.20095(9) 0.22379(17) 0.24512(6) 0.0356(3) Uani 1 1 d . . . . .
H2 H 0.2099 0.1895 0.2041 0.043 Uiso 1 1 calc R U . . .
C10 C 0.12398(9) 0.18701(18) 0.26084(6) 0.0369(3) Uani 1 1 d . . . . .
H3 H 0.0829 0.1293 0.2302 0.044 Uiso 1 1 calc R U . . .
C11 C 0.10795(8) 0.23501(17) 0.32118(6) 0.0330(3) Uani 1 1 d . . . . .
H4 H 0.0567 0.2122 0.3320 0.040 Uiso 1 1 calc R U . . .
C12 C 0.17201(7) 0.31893(15) 0.36486(6) 0.0263(2) Uani 1 1 d . . . . .
C13 C 0.15152(7) 0.49090(16) 0.58512(6) 0.0288(3) Uani 1 1 d . . . . .
H5 H 0.1977 0.5079 0.6238 0.035 Uiso 1 1 calc R U . . .
H9 H 0.1213 0.3913 0.5929 0.035 Uiso 1 1 calc R U . . .
C14 C 0.09267(8) 0.63897(18) 0.57739(7) 0.0358(3) Uani 1 1 d . . . . .
H7 H 0.1236 0.7392 0.5740 0.054 Uiso 1 1 calc R U . . .
H8 H 0.0683 0.6462 0.6156 0.054 Uiso 1 1 calc R U . . .
H6 H 0.0487 0.6256 0.5377 0.054 Uiso 1 1 calc R U . . .
C15 C 0.48501(8) 0.60711(18) 0.59899(6) 0.0349(3) Uani 1 1 d . . . . .
H12 H 0.5388 0.5769 0.5951 0.042 Uiso 1 1 calc R U . . .
C16 C 0.41506(7) 0.53857(17) 0.55630(6) 0.0296(3) Uani 1 1 d . . . . .
H13 H 0.4221 0.4627 0.5238 0.036 Uiso 1 1 calc R U . . .


_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 C6 1.3386(15) . ?
N1 C7 1.3845(15) . ?
N2 N3 1.3387(13) . ?
N2 C6 1.3757(14) . ?
N2 C12 1.3873(15) . ?
N3 N4 1.3421(14) . ?
N4 C5 1.3637(14) . ?
N4 C13 1.4709(14) . ?
C1 C2 1.3819(19) . ?
C1 C15 1.386(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.3845(18) . ?
C2 H14 0.9300 . ?
C3 C4 1.3960(17) . ?
C3 H11 0.9300 . ?
C4 C16 1.3992(16) . ?
C4 C5 1.4602(16) . ?
C5 C6 1.4076(16) . ?
C7 C8 1.4057(17) . ?
C7 C12 1.4125(16) . ?
C8 C9 1.3737(19) . ?
C8 H10 0.9300 . ?
C9 C10 1.3973(19) . ?
C9 H2 0.9300 . ?
C10 C11 1.3799(18) . ?
C10 H3 0.9300 . ?
C11 C12 1.3852(17) . ?
C11 H4 0.9300 . ?
C13 C14 1.5115(18) . ?
C13 H5 0.9700 . ?
C13 H9 0.9700 . ?
C14 H7 0.9600 . ?
C14 H8 0.9600 . ?
C14 H6 0.9600 . ?
C15 C16 1.3831(17) . ?
C15 H12 0.9300 . ?
C16 H13 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
C6 N1 C7 102.97(9) . . ?
N3 N2 C6 114.56(10) . . ?
N3 N2 C12 137.31(10) . . ?
C6 N2 C12 108.13(9) . . ?
N2 N3 N4 101.82(9) . . ?
N3 N4 C5 115.17(9) . . ?
N3 N4 C13 114.76(9) . . ?
C5 N4 C13 130.04(10) . . ?
C2 C1 C15 119.77(12) . . ?
C2 C1 H1 120.1 . . ?
C15 C1 H1 120.1 . . ?
C1 C2 C3 120.26(12) . . ?
C1 C2 H14 119.9 . . ?
C3 C2 H14 119.9 . . ?
C2 C3 C4 120.64(11) . . ?
C2 C3 H11 119.7 . . ?
C4 C3 H11 119.7 . . ?
C3 C4 C16 118.51(11) . . ?
C3 C4 C5 123.99(10) . . ?
C16 C4 C5 117.49(11) . . ?
N4 C5 C6 104.16(10) . . ?
N4 C5 C4 127.70(10) . . ?
C6 C5 C4 128.08(10) . . ?
N1 C6 N2 113.02(10) . . ?
N1 C6 C5 142.66(11) . . ?
N2 C6 C5 104.29(9) . . ?
N1 C7 C8 129.33(11) . . ?
N1 C7 C12 113.02(10) . . ?
C8 C7 C12 117.63(11) . . ?
C9 C8 C7 118.65(12) . . ?
C9 C8 H10 120.7 . . ?
C7 C8 H10 120.7 . . ?
C8 C9 C10 122.18(12) . . ?
C8 C9 H2 118.9 . . ?
C10 C9 H2 118.9 . . ?
C11 C10 C9 120.97(12) . . ?
C11 C10 H3 119.5 . . ?
C9 C10 H3 119.5 . . ?
C10 C11 C12 116.62(12) . . ?
C10 C11 H4 121.7 . . ?
C12 C11 H4 121.7 . . ?
C11 C12 N2 133.19(11) . . ?
C11 C12 C7 123.93(11) . . ?
N2 C12 C7 102.85(10) . . ?
N4 C13 C14 111.71(10) . . ?
N4 C13 H5 109.3 . . ?
C14 C13 H5 109.3 . . ?
N4 C13 H9 109.3 . . ?
C14 C13 H9 109.3 . . ?
H5 C13 H9 107.9 . . ?
C13 C14 H7 109.5 . . ?
C13 C14 H8 109.5 . . ?
H7 C14 H8 109.5 . . ?
C13 C14 H6 109.5 . . ?
H7 C14 H6 109.5 . . ?
H8 C14 H6 109.5 . . ?
C16 C15 C1 120.29(12) . . ?
C16 C15 H12 119.9 . . ?
C1 C15 H12 119.9 . . ?
C15 C16 C4 120.51(12) . . ?
C15 C16 H13 119.7 . . ?
C4 C16 H13 119.7 . . ?

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
C6 N2 N3 N4 -0.10(13) . . . . ?
C12 N2 N3 N4 -179.66(13) . . . . ?
N2 N3 N4 C5 0.14(13) . . . . ?
N2 N3 N4 C13 -178.09(9) . . . . ?
C15 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C2 C3 C4 C16 -1.92(18) . . . . ?
C2 C3 C4 C5 179.71(11) . . . . ?
N3 N4 C5 C6 -0.13(13) . . . . ?
C13 N4 C5 C6 177.78(11) . . . . ?
N3 N4 C5 C4 -177.37(11) . . . . ?
C13 N4 C5 C4 0.5(2) . . . . ?
C3 C4 C5 N4 -32.97(19) . . . . ?
C16 C4 C5 N4 148.65(12) . . . . ?
C3 C4 C5 C6 150.43(12) . . . . ?
C16 C4 C5 C6 -27.95(18) . . . . ?
C7 N1 C6 N2 -1.01(13) . . . . ?
C7 N1 C6 C5 -178.80(16) . . . . ?
N3 N2 C6 N1 -178.58(10) . . . . ?
C12 N2 C6 N1 1.10(14) . . . . ?
N3 N2 C6 C5 0.03(13) . . . . ?
C12 N2 C6 C5 179.71(10) . . . . ?
N4 C5 C6 N1 177.95(15) . . . . ?
C4 C5 C6 N1 -4.8(3) . . . . ?
N4 C5 C6 N2 0.05(12) . . . . ?
C4 C5 C6 N2 177.28(11) . . . . ?
C6 N1 C7 C8 -177.71(13) . . . . ?
C6 N1 C7 C12 0.58(13) . . . . ?
N1 C7 C8 C9 177.12(12) . . . . ?
C12 C7 C8 C9 -1.11(18) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 N2 -177.08(13) . . . . ?
C10 C11 C12 C7 0.61(19) . . . . ?
N3 N2 C12 C11 -3.0(2) . . . . ?
C6 N2 C12 C11 177.39(13) . . . . ?
N3 N2 C12 C7 178.93(13) . . . . ?
C6 N2 C12 C7 -0.64(13) . . . . ?
N1 C7 C12 C11 -178.23(11) . . . . ?
C8 C7 C12 C11 0.28(18) . . . . ?
N1 C7 C12 N2 0.04(13) . . . . ?
C8 C7 C12 N2 178.55(11) . . . . ?
N3 N4 C13 C14 -79.66(13) . . . . ?
C5 N4 C13 C14 102.43(14) . . . . ?
C2 C1 C15 C16 -0.5(2) . . . . ?
C1 C15 C16 C4 -0.2(2) . . . . ?
C3 C4 C16 C15 1.45(18) . . . . ?
C5 C4 C16 C15 179.92(11) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.049

