# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 1420103'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N4'
_chemical_formula_weight         326.39

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                   9.532(3)
_cell_length_b                   9.630(3)
_cell_length_c                   17.838(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.075(7)
_cell_angle_gamma                90.00
_cell_volume                     1621.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    930
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      20.71

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9526
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            12805
_diffrn_reflns_av_R_equivalents  0.1667
_diffrn_reflns_av_sigmaI/netI    0.1096
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         23.17
_reflns_number_total             2293
_reflns_number_gt                1363
_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    'Mercury 3.1'
_computing_publication_material  'Ortep 3v.2'

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2293
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   0.777
_refine_ls_restrained_S_all      0.777
_refine_ls_shift/su_max          0.001
_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
N3 N 0.1853(3) 0.6175(3) 0.60448(15) 0.0249(7) Uani 1 1 d . . .
N1 N -0.0287(3) 0.8130(3) 0.55671(15) 0.0245(7) Uani 1 1 d . . .
N2 N 0.0139(3) 0.7350(3) 0.50646(15) 0.0249(7) Uani 1 1 d . . .
N4 N 0.2814(3) 0.4688(3) 0.52730(15) 0.0271(7) Uani 1 1 d . . .
C3 C -0.1378(3) 0.9063(3) 0.52574(17) 0.0213(8) Uani 1 1 d . . .
C11 C 0.2830(3) 0.5118(3) 0.59922(19) 0.0260(8) Uani 1 1 d . . .
C13 C 0.1183(3) 0.6413(3) 0.53069(17) 0.0235(8) Uani 1 1 d . . .
C12 C 0.1811(3) 0.5477(3) 0.48469(18) 0.0227(8) Uani 1 1 d . . .
C14 C 0.1555(3) 0.5301(3) 0.40239(18) 0.0251(8) Uani 1 1 d . . .
C2 C -0.1829(3) 1.0012(3) 0.57555(18) 0.0260(8) Uani 1 1 d . . .
H2 H -0.1422 1.0010 0.6261 0.031 Uiso 1 1 calc R . .
C10 C 0.3719(3) 0.4664(3) 0.66430(19) 0.0300(9) Uani 1 1 d . . .
C6 C -0.3507(3) 1.0999(3) 0.47563(18) 0.0240(8) Uani 1 1 d . . .
C15 C 0.2205(4) 0.4198(4) 0.3705(2) 0.0331(9) Uani 1 1 d . . .
H15 H 0.2761 0.3576 0.4016 0.040 Uiso 1 1 calc R . .
C8 C 0.2565(4) 0.6366(4) 0.7343(2) 0.0334(9) Uani 1 1 d . . .
H8 H 0.2484 0.6782 0.7806 0.040 Uiso 1 1 calc R . .
C4 C -0.1997(3) 0.9086(3) 0.45053(18) 0.0281(8) Uani 1 1 d . . .
H4 H -0.1711 0.8453 0.4163 0.034 Uiso 1 1 calc R . .
C20 C 0.4788(4) 0.3566(4) 0.6561(2) 0.0379(10) Uani 1 1 d . . .
H20A H 0.5497 0.3929 0.6282 0.057 Uiso 1 1 calc R . .
H20B H 0.4329 0.2787 0.6294 0.057 Uiso 1 1 calc R . .
H20C H 0.5226 0.3274 0.7053 0.057 Uiso 1 1 calc R . .
C19 C 0.0722(4) 0.6214(4) 0.35432(19) 0.0326(9) Uani 1 1 d . . .
H19 H 0.0274 0.6954 0.3746 0.039 Uiso 1 1 calc R . .
C1 C -0.2879(3) 1.0964(3) 0.55074(18) 0.0270(8) Uani 1 1 d . . .
H1 H -0.3171 1.1593 0.5850 0.032 Uiso 1 1 calc R . .
C9 C 0.3574(4) 0.5301(4) 0.7317(2) 0.0337(9) Uani 1 1 d . . .
H9 H 0.4145 0.5028 0.7759 0.040 Uiso 1 1 calc R . .
C18 C 0.0556(4) 0.6025(4) 0.2768(2) 0.0379(10) Uani 1 1 d . . .
H18 H -0.0002 0.6639 0.2452 0.046 Uiso 1 1 calc R . .
C7 C 0.1715(4) 0.6800(4) 0.67190(18) 0.0305(9) Uani 1 1 d . . .
H7 H 0.1054 0.7503 0.6746 0.037 Uiso 1 1 calc R . .
C16 C 0.2030(4) 0.4022(4) 0.2927(2) 0.0366(10) Uani 1 1 d . . .
H16 H 0.2468 0.3280 0.2719 0.044 Uiso 1 1 calc R . .
C21 C -0.4667(3) 1.2017(3) 0.4492(2) 0.0295(9) Uani 1 1 d . . .
H21A H -0.4621 1.2267 0.3975 0.044 Uiso 1 1 calc R . .
H21B H -0.4552 1.2834 0.4804 0.044 Uiso 1 1 calc R . .
H21C H -0.5570 1.1601 0.4529 0.044 Uiso 1 1 calc R . .
C17 C 0.1217(4) 0.4930(4) 0.2460(2) 0.0368(9) Uani 1 1 d . . .
H17 H 0.1111 0.4810 0.1937 0.044 Uiso 1 1 calc R . .
C5 C -0.3036(3) 1.0044(3) 0.42650(19) 0.0297(8) Uani 1 1 d . . .
H5 H -0.3434 1.0051 0.3758 0.036 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
N3 C7 1.367(4) . ?
N3 C11 1.392(4) . ?
N3 C13 1.399(4) . ?
N1 N2 1.279(4) . ?
N1 C3 1.425(4) . ?
N2 C13 1.367(4) . ?
N4 C11 1.346(4) . ?
N4 C12 1.365(4) . ?
C3 C2 1.384(4) . ?
C3 C4 1.388(4) . ?
C11 C10 1.407(5) . ?
C13 C12 1.408(4) . ?
C12 C14 1.464(4) . ?
C14 C15 1.390(5) . ?
C14 C19 1.396(5) . ?
C2 C1 1.384(4) . ?
C10 C9 1.374(5) . ?
C10 C20 1.490(5) . ?
C6 C5 1.388(5) . ?
C6 C1 1.389(5) . ?
C6 C21 1.503(4) . ?
C15 C16 1.385(5) . ?
C8 C7 1.349(5) . ?
C8 C9 1.411(5) . ?
C4 C5 1.377(4) . ?
C19 C18 1.382(5) . ?
C18 C17 1.381(5) . ?
C16 C17 1.370(5) . ?

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
C7 N3 C11 122.0(3) . . ?
C7 N3 C13 131.9(3) . . ?
C11 N3 C13 106.1(3) . . ?
N2 N1 C3 112.6(3) . . ?
N1 N2 C13 117.0(3) . . ?
C11 N4 C12 105.8(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 N1 116.3(3) . . ?
C4 C3 N1 124.9(3) . . ?
N4 C11 N3 111.8(3) . . ?
N4 C11 C10 128.0(3) . . ?
N3 C11 C10 120.1(3) . . ?
N2 C13 N3 128.4(3) . . ?
N2 C13 C12 126.0(3) . . ?
N3 C13 C12 105.5(3) . . ?
N4 C12 C13 110.7(3) . . ?
N4 C12 C14 119.9(3) . . ?
C13 C12 C14 129.3(3) . . ?
C15 C14 C19 118.5(3) . . ?
C15 C14 C12 118.5(3) . . ?
C19 C14 C12 122.9(3) . . ?
C1 C2 C3 120.5(3) . . ?
C9 C10 C11 117.5(3) . . ?
C9 C10 C20 123.8(3) . . ?
C11 C10 C20 118.7(3) . . ?
C5 C6 C1 117.3(3) . . ?
C5 C6 C21 121.6(3) . . ?
C1 C6 C21 121.1(3) . . ?
C16 C15 C14 120.3(3) . . ?
C7 C8 C9 122.1(3) . . ?
C5 C4 C3 120.1(3) . . ?
C18 C19 C14 120.5(3) . . ?
C2 C1 C6 121.3(3) . . ?
C10 C9 C8 120.3(3) . . ?
C17 C18 C19 120.3(3) . . ?
C8 C7 N3 118.0(3) . . ?
C17 C16 C15 120.6(3) . . ?
C16 C17 C18 119.7(3) . . ?
C4 C5 C6 122.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.17
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.059
