# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_222
_database_code_depnum_ccdc_archive 'CCDC 1870772'
loop_
_audit_author_name
_audit_author_address
'Pengfei Chen'
;ANHUI UNIVERSITY
China
;
_audit_update_record             
;
2019-01-31 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N4'
_chemical_formula_weight         412.48

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   'Cc   '

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'

_cell_length_a                   15.827(5)
_cell_length_b                   13.169(5)
_cell_length_c                   10.544(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.918(6)
_cell_angle_gamma                90.00
_cell_volume                     2102.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1748
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.49

_exptl_crystal_description       ?
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9899
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   ??(SADABS;Sheldrick,2003)??

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7243
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3228
_reflns_number_gt                2534
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0558P)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     SHELXL
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         3228
_refine_ls_number_parameters     290
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N3 N 0.26771(15) 0.10947(17) 0.3211(2) 0.0255(6) Uani 1 1 d . . .
N2 N 0.39018(15) -0.06677(19) 0.5682(2) 0.0289(6) Uani 1 1 d . . .
N4 N 0.10870(17) 0.30008(19) 0.1583(3) 0.0362(7) Uani 1 1 d . . .
N1 N -0.24046(19) 0.1544(2) 1.1763(3) 0.0428(7) Uani 1 1 d . . .
C25 C 0.2287(2) 0.2310(2) 0.0898(3) 0.0307(8) Uani 1 1 d . . .
H25 H 0.2770 0.1875 0.1060 0.037 Uiso 1 1 calc R . .
C4 C -0.2111(2) 0.0963(2) 0.9764(3) 0.0350(8) Uani 1 1 d . . .
H4 H -0.2293 0.0567 0.9003 0.042 Uiso 1 1 calc R . .
C17 C 0.36547(17) -0.0154(2) 0.4530(3) 0.0231(7) Uani 1 1 d . . .
C8 C -0.0262(2) 0.1066(2) 0.7198(3) 0.0282(7) Uani 1 1 d . . .
C24 C 0.17703(18) 0.2349(2) 0.1768(3) 0.0258(7) Uani 1 1 d . . .
C14 C 0.15597(18) 0.1045(2) 0.4849(3) 0.0253(7) Uani 1 1 d . . .
C16 C 0.28585(17) 0.0501(2) 0.4300(3) 0.0224(6) Uani 1 1 d . . .
C23 C 0.19480(19) 0.1674(2) 0.2944(3) 0.0257(7) Uani 1 1 d . . .
C18 C 0.41147(17) -0.0248(2) 0.3588(3) 0.0265(7) Uani 1 1 d . . .
H18 H 0.3930 0.0104 0.2791 0.032 Uiso 1 1 calc R . .
C5 C -0.1340(2) 0.1532(2) 1.0025(3) 0.0315(8) Uani 1 1 d . . .
C15 C 0.23287(18) 0.0472(2) 0.5153(3) 0.0258(7) Uani 1 1 d . . .
H15 H 0.2489 0.0074 0.5914 0.031 Uiso 1 1 calc R . .
C21 C 0.4611(2) -0.1259(2) 0.5922(3) 0.0339(8) Uani 1 1 d . . .
H21 H 0.4782 -0.1610 0.6722 0.041 Uiso 1 1 calc R . .
C20 C 0.5113(2) -0.1385(2) 0.5053(3) 0.0321(8) Uani 1 1 d . . .
H20 H 0.5610 -0.1800 0.5268 0.038 Uiso 1 1 calc R . .
C13 C 0.09364(19) 0.1018(2) 0.5673(3) 0.0253(7) Uani 1 1 d . . .
C10 C 0.12353(19) 0.1052(2) 0.7050(3) 0.0283(7) Uani 1 1 d . . .
H10 H 0.1839 0.1055 0.7474 0.034 Uiso 1 1 calc R . .
C6 C -0.0738(2) 0.1507(2) 0.9190(3) 0.0338(8) Uani 1 1 d . . .
H6 H -0.0182 0.1792 0.9554 0.041 Uiso 1 1 calc R . .
C12 C 0.00296(19) 0.0985(2) 0.5067(3) 0.0276(7) Uani 1 1 d . . .
H12 H -0.0184 0.0952 0.4148 0.033 Uiso 1 1 calc R . .
C22 C 0.1369(2) 0.1653(2) 0.3726(3) 0.0269(7) Uani 1 1 d . . .
H22 H 0.0858 0.2045 0.3493 0.032 Uiso 1 1 calc R . .
C9 C 0.06483(19) 0.1081(2) 0.7801(3) 0.0300(8) Uani 1 1 d . . .
H9 H 0.0864 0.1110 0.8720 0.036 Uiso 1 1 calc R . .
C7 C -0.0901(2) 0.1122(2) 0.7967(3) 0.0314(8) Uani 1 1 d . . .
H7 H -0.1465 0.0869 0.7572 0.038 Uiso 1 1 calc R . .
C11 C -0.0562(2) 0.1000(2) 0.5820(3) 0.0290(7) Uani 1 1 d . . .
H11 H -0.1165 0.0965 0.5398 0.035 Uiso 1 1 calc R . .
C1 C -0.1668(2) 0.2089(3) 1.1995(4) 0.0442(9) Uani 1 1 d . . .
H1 H -0.1507 0.2486 1.2757 0.053 Uiso 1 1 calc R . .
C2 C -0.1123(2) 0.2103(3) 1.1173(3) 0.0395(9) Uani 1 1 d . . .
H2 H -0.0614 0.2498 1.1395 0.047 Uiso 1 1 calc R . .
C27 C 0.1360(2) 0.3581(2) -0.0415(3) 0.0397(9) Uani 1 1 d . . .
H27 H 0.1198 0.4002 -0.1155 0.048 Uiso 1 1 calc R . .
C19 C 0.48531(19) -0.0875(2) 0.3858(3) 0.0312(7) Uani 1 1 d . . .
H19 H 0.5167 -0.0950 0.3243 0.037 Uiso 1 1 calc R . .
C26 C 0.2069(2) 0.2931(2) -0.0215(3) 0.0350(8) Uani 1 1 d . . .
H26 H 0.2396 0.2908 -0.0817 0.042 Uiso 1 1 calc R . .
C3 C -0.2606(2) 0.0994(3) 1.0657(3) 0.0404(9) Uani 1 1 d . . .
H3 H -0.3116 0.0602 1.0467 0.048 Uiso 1 1 calc R . .
C28 C 0.0893(2) 0.3594(3) 0.0515(3) 0.0413(9) Uani 1 1 d . . .
H28 H 0.0420 0.4041 0.0385 0.050 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 C23 1.343(4) . ?
N3 C16 1.349(4) . ?
N2 C21 1.329(4) . ?
N2 C17 1.345(4) . ?
N4 C28 1.332(4) . ?
N4 C24 1.349(4) . ?
N1 C3 1.330(4) . ?
N1 C1 1.330(4) . ?
C25 C26 1.388(4) . ?
C25 C24 1.397(4) . ?
C25 H25 0.9300 . ?
C4 C5 1.389(4) . ?
C4 C3 1.390(4) . ?
C4 H4 0.9300 . ?
C17 C18 1.397(4) . ?
C17 C16 1.488(4) . ?
C8 C11 1.393(4) . ?
C8 C9 1.395(4) . ?
C8 C7 1.472(4) . ?
C24 C23 1.484(4) . ?
C14 C15 1.388(4) . ?
C14 C22 1.389(4) . ?
C14 C13 1.492(4) . ?
C16 C15 1.397(4) . ?
C23 C22 1.399(4) . ?
C18 C19 1.391(4) . ?
C18 H18 0.9300 . ?
C5 C2 1.381(4) . ?
C5 C6 1.473(4) . ?
C15 H15 0.9300 . ?
C21 C20 1.387(4) . ?
C21 H21 0.9300 . ?
C20 C19 1.380(4) . ?
C20 H20 0.9300 . ?
C13 C10 1.391(4) . ?
C13 C12 1.391(4) . ?
C10 C9 1.385(4) . ?
C10 H10 0.9300 . ?
C6 C7 1.339(4) . ?
C6 H6 0.9300 . ?
C12 C11 1.393(4) . ?
C12 H12 0.9300 . ?
C22 H22 0.9300 . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C11 H11 0.9300 . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C27 C26 1.378(4) . ?
C27 C28 1.390(4) . ?
C27 H27 0.9300 . ?
C19 H19 0.9300 . ?
C26 H26 0.9300 . ?
C3 H3 0.9300 . ?
C28 H28 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
C23 N3 C16 117.7(2) . . ?
C21 N2 C17 118.3(3) . . ?
C28 N4 C24 118.3(3) . . ?
C3 N1 C1 115.3(3) . . ?
C26 C25 C24 118.9(3) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N2 C17 C18 121.5(2) . . ?
N2 C17 C16 116.6(2) . . ?
C18 C17 C16 121.9(2) . . ?
C11 C8 C9 118.0(2) . . ?
C11 C8 C7 119.9(3) . . ?
C9 C8 C7 122.2(3) . . ?
N4 C24 C25 121.8(3) . . ?
N4 C24 C23 116.8(2) . . ?
C25 C24 C23 121.4(3) . . ?
C15 C14 C22 117.9(3) . . ?
C15 C14 C13 122.5(3) . . ?
C22 C14 C13 119.6(3) . . ?
N3 C16 C15 123.0(2) . . ?
N3 C16 C17 115.8(2) . . ?
C15 C16 C17 121.2(2) . . ?
N3 C23 C22 122.3(3) . . ?
N3 C23 C24 117.3(2) . . ?
C22 C23 C24 120.4(3) . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C2 C5 C4 116.5(3) . . ?
C2 C5 C6 119.8(3) . . ?
C4 C5 C6 123.6(3) . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N2 C21 C20 124.0(3) . . ?
N2 C21 H21 118.0 . . ?
C20 C21 H21 118.0 . . ?
C19 C20 C21 118.0(3) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C10 C13 C12 118.2(3) . . ?
C10 C13 C14 121.7(3) . . ?
C12 C13 C14 120.1(3) . . ?
C9 C10 C13 121.1(3) . . ?
C9 C10 H10 119.5 . . ?
C13 C10 H10 119.5 . . ?
C7 C6 C5 127.3(3) . . ?
C7 C6 H6 116.3 . . ?
C5 C6 H6 116.3 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C22 C23 119.8(3) . . ?
C14 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C6 C7 C8 125.4(3) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C12 C11 C8 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C8 C11 H11 119.5 . . ?
N1 C1 C2 124.2(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C5 C2 C1 120.0(3) . . ?
C5 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C26 C27 C28 118.4(3) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C27 C26 C25 119.2(3) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
N1 C3 C4 124.9(3) . . ?
N1 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
N4 C28 C27 123.4(3) . . ?
N4 C28 H28 118.3 . . ?
C27 C28 H28 118.3 . . ?

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
C21 N2 C17 C18 1.3(4) . . . . ?
C21 N2 C17 C16 -179.9(3) . . . . ?
C28 N4 C24 C25 2.1(4) . . . . ?
C28 N4 C24 C23 -177.9(3) . . . . ?
C26 C25 C24 N4 -2.5(4) . . . . ?
C26 C25 C24 C23 177.4(3) . . . . ?
C23 N3 C16 C15 -0.5(4) . . . . ?
C23 N3 C16 C17 177.9(2) . . . . ?
N2 C17 C16 N3 172.9(2) . . . . ?
C18 C17 C16 N3 -8.2(4) . . . . ?
N2 C17 C16 C15 -8.6(4) . . . . ?
C18 C17 C16 C15 170.3(3) . . . . ?
C16 N3 C23 C22 -2.1(4) . . . . ?
C16 N3 C23 C24 178.1(2) . . . . ?
N4 C24 C23 N3 -173.6(3) . . . . ?
C25 C24 C23 N3 6.4(4) . . . . ?
N4 C24 C23 C22 6.6(4) . . . . ?
C25 C24 C23 C22 -173.4(3) . . . . ?
N2 C17 C18 C19 -1.0(4) . . . . ?
C16 C17 C18 C19 -179.8(3) . . . . ?
C3 C4 C5 C2 -0.5(4) . . . . ?
C3 C4 C5 C6 176.2(3) . . . . ?
C22 C14 C15 C16 -2.3(4) . . . . ?
C13 C14 C15 C16 177.0(3) . . . . ?
N3 C16 C15 C14 2.8(4) . . . . ?
C17 C16 C15 C14 -175.6(3) . . . . ?
C17 N2 C21 C20 -0.3(4) . . . . ?
N2 C21 C20 C19 -0.9(5) . . . . ?
C15 C14 C13 C10 44.2(4) . . . . ?
C22 C14 C13 C10 -136.5(3) . . . . ?
C15 C14 C13 C12 -137.4(3) . . . . ?
C22 C14 C13 C12 41.9(4) . . . . ?
C12 C13 C10 C9 -1.8(5) . . . . ?
C14 C13 C10 C9 176.6(3) . . . . ?
C2 C5 C6 C7 -169.4(3) . . . . ?
C4 C5 C6 C7 14.0(5) . . . . ?
C10 C13 C12 C11 0.9(5) . . . . ?
C14 C13 C12 C11 -177.5(2) . . . . ?
C15 C14 C22 C23 -0.2(4) . . . . ?
C13 C14 C22 C23 -179.5(3) . . . . ?
N3 C23 C22 C14 2.5(4) . . . . ?
C24 C23 C22 C14 -177.7(3) . . . . ?
C13 C10 C9 C8 0.7(5) . . . . ?
C11 C8 C9 C10 1.3(4) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
C5 C6 C7 C8 -176.5(3) . . . . ?
C11 C8 C7 C6 -157.0(3) . . . . ?
C9 C8 C7 C6 22.7(5) . . . . ?
C13 C12 C11 C8 1.1(5) . . . . ?
C9 C8 C11 C12 -2.2(5) . . . . ?
C7 C8 C11 C12 177.5(3) . . . . ?
C3 N1 C1 C2 -0.4(5) . . . . ?
C4 C5 C2 C1 -0.1(5) . . . . ?
C6 C5 C2 C1 -176.9(3) . . . . ?
N1 C1 C2 C5 0.5(6) . . . . ?
C21 C20 C19 C18 1.2(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C28 C27 C26 C25 0.4(5) . . . . ?
C24 C25 C26 C27 1.2(5) . . . . ?
C1 N1 C3 C4 -0.2(5) . . . . ?
C5 C4 C3 N1 0.7(5) . . . . ?
C24 N4 C28 C27 -0.3(5) . . . . ?
C26 C27 C28 N4 -0.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043
