# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1977107'
loop_
_audit_author_name
_audit_author_address
yapinggong
;Renmin University of China
China
;
_audit_update_record             
;
2020-01-13 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 N4'
_chemical_formula_weight         246.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8961(2)
_cell_length_b                   12.3330(3)
_cell_length_c                   13.6728(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.385(2)
_cell_angle_gamma                90
_cell_volume                     1155.65(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    1182
_cell_measurement_theta_min      4.843
_cell_measurement_theta_max      49.991

_exptl_crystal_description       cube
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_reflns_number            7403
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.843
_diffrn_reflns_theta_max         72.057
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2241
_reflns_number_gt                2055
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0855P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2241
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.68785(12) 0.29939(7) 0.45610(6) 0.0201(2) Uani 1 1 d . . . . .
N2 N 0.49071(18) 0.45374(8) 0.13940(7) 0.0405(3) Uani 1 1 d . . . . .
N3 N 0.76428(16) 0.36004(8) 0.61578(7) 0.0307(3) Uani 1 1 d . . . . .
H3A H 0.797(2) 0.4222(12) 0.6511(11) 0.037 Uiso 1 1 d . U . . .
N4 N 0.84250(13) 0.57825(8) 0.64061(6) 0.0246(2) Uani 1 1 d . . . . .
C1 C 0.70445(16) 0.19560(9) 0.49449(8) 0.0259(3) Uani 1 1 d . . . . .
H1A H 0.7471 0.1864 0.5609 0.031 Uiso 1 1 calc R U . . .
C2 C 0.66023(16) 0.10725(9) 0.43789(9) 0.0279(3) Uani 1 1 d . . . . .
H2A H 0.6744 0.0382 0.4651 0.034 Uiso 1 1 calc R U . . .
C3 C 0.59257(16) 0.12010(9) 0.33739(8) 0.0260(3) Uani 1 1 d . . . . .
H3C H 0.5586 0.0600 0.2982 0.031 Uiso 1 1 calc R U . . .
C4 C 0.57775(15) 0.22198(9) 0.29859(8) 0.0231(3) Uani 1 1 d . . . . .
H4B H 0.5336 0.2310 0.2323 0.028 Uiso 1 1 calc R U . . .
C5 C 0.62856(14) 0.31448(8) 0.35756(7) 0.0199(2) Uani 1 1 d . . . . .
C6 C 0.62124(15) 0.42068(8) 0.32082(7) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.67881(14) 0.50797(8) 0.38308(7) 0.0209(3) Uani 1 1 d . . . . .
H7A H 0.6774 0.5772 0.3561 0.025 Uiso 1 1 calc R U . . .
C8 C 0.73717(14) 0.49631(8) 0.48180(7) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.73412(15) 0.38847(8) 0.52574(7) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.54982(17) 0.43830(8) 0.22051(8) 0.0275(3) Uani 1 1 d . . . . .
C11 C 0.79476(14) 0.59300(8) 0.54326(7) 0.0207(3) Uani 1 1 d . . . . .
C12 C 0.79908(16) 0.69753(9) 0.50239(8) 0.0252(3) Uani 1 1 d . . . . .
H12A H 0.7671 0.7074 0.4351 0.030 Uiso 1 1 calc R U . . .
C13 C 0.85068(16) 0.78554(9) 0.56209(8) 0.0273(3) Uani 1 1 d . . . . .
H13A H 0.8551 0.8547 0.5353 0.033 Uiso 1 1 calc R U . . .
C14 C 0.89581(15) 0.76957(9) 0.66237(8) 0.0280(3) Uani 1 1 d . . . . .
H14A H 0.9284 0.8275 0.7046 0.034 Uiso 1 1 calc R U . . .
C15 C 0.89071(16) 0.66504(10) 0.69731(8) 0.0279(3) Uani 1 1 d . . . . .
H15A H 0.9227 0.6539 0.7644 0.034 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 C5 1.3764(13) . ?
N1 C1 1.3834(13) . ?
N1 C9 1.4656(13) . ?
N2 C10 1.1541(15) . ?
N3 C9 1.2746(14) . ?
N3 H3A 0.921(15) . ?
N4 C15 1.3416(14) . ?
N4 C11 1.3475(14) . ?
C1 C2 1.3515(16) . ?
C1 H1A 0.9300 . ?
C2 C3 1.4101(16) . ?
C2 H2A 0.9300 . ?
C3 C4 1.3633(15) . ?
C3 H3C 0.9300 . ?
C4 C5 1.4183(14) . ?
C4 H4B 0.9300 . ?
C5 C6 1.4017(14) . ?
C6 C7 1.4022(14) . ?
C6 C10 1.4215(14) . ?
C7 C8 1.3726(14) . ?
C7 H7A 0.9300 . ?
C8 C9 1.4605(14) . ?
C8 C11 1.4871(14) . ?
C11 C12 1.4067(15) . ?
C12 C13 1.3808(15) . ?
C12 H12A 0.9300 . ?
C13 C14 1.3859(16) . ?
C13 H13A 0.9300 . ?
C14 C15 1.3767(17) . ?
C14 H14A 0.9300 . ?
C15 H15A 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
C5 N1 C1 119.97(9) . . ?
C5 N1 C9 123.65(8) . . ?
C1 N1 C9 116.37(9) . . ?
C9 N3 H3A 106.4(9) . . ?
C15 N4 C11 118.73(10) . . ?
C2 C1 N1 121.66(10) . . ?
C2 C1 H1A 119.2 . . ?
N1 C1 H1A 119.2 . . ?
C1 C2 C3 119.76(10) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 119.03(10) . . ?
C4 C3 H3C 120.5 . . ?
C2 C3 H3C 120.5 . . ?
C3 C4 C5 121.13(10) . . ?
C3 C4 H4B 119.4 . . ?
C5 C4 H4B 119.4 . . ?
N1 C5 C6 118.17(9) . . ?
N1 C5 C4 118.39(9) . . ?
C6 C5 C4 123.44(9) . . ?
C7 C6 C5 120.22(9) . . ?
C7 C6 C10 120.84(9) . . ?
C5 C6 C10 118.91(9) . . ?
C8 C7 C6 123.29(9) . . ?
C8 C7 H7A 118.4 . . ?
C6 C7 H7A 118.4 . . ?
C7 C8 C9 118.94(9) . . ?
C7 C8 C11 120.16(9) . . ?
C9 C8 C11 120.86(9) . . ?
N3 C9 C8 129.75(10) . . ?
N3 C9 N1 114.94(9) . . ?
C8 C9 N1 115.30(9) . . ?
N2 C10 C6 179.16(13) . . ?
N4 C11 C12 120.16(9) . . ?
N4 C11 C8 118.07(9) . . ?
C12 C11 C8 121.77(9) . . ?
C13 C12 C11 120.07(10) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 119.21(10) . . ?
C12 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C15 C14 C13 117.69(10) . . ?
C15 C14 H14A 121.2 . . ?
C13 C14 H14A 121.2 . . ?
N4 C15 C14 124.12(10) . . ?
N4 C15 H15A 117.9 . . ?
C14 C15 H15A 117.9 . . ?

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
C5 N1 C1 C2 -1.26(16) . . . . ?
C9 N1 C1 C2 178.08(10) . . . . ?
N1 C1 C2 C3 -0.95(17) . . . . ?
C1 C2 C3 C4 1.64(16) . . . . ?
C2 C3 C4 C5 -0.17(16) . . . . ?
C1 N1 C5 C6 -177.45(8) . . . . ?
C9 N1 C5 C6 3.26(15) . . . . ?
C1 N1 C5 C4 2.67(15) . . . . ?
C9 N1 C5 C4 -176.62(8) . . . . ?
C3 C4 C5 N1 -1.97(15) . . . . ?
C3 C4 C5 C6 178.16(9) . . . . ?
N1 C5 C6 C7 1.87(15) . . . . ?
C4 C5 C6 C7 -178.26(9) . . . . ?
N1 C5 C6 C10 -176.46(9) . . . . ?
C4 C5 C6 C10 3.41(15) . . . . ?
C5 C6 C7 C8 -2.52(16) . . . . ?
C10 C6 C7 C8 175.78(9) . . . . ?
C6 C7 C8 C9 -1.96(16) . . . . ?
C6 C7 C8 C11 -179.54(8) . . . . ?
C7 C8 C9 N3 -172.94(10) . . . . ?
C11 C8 C9 N3 4.62(17) . . . . ?
C7 C8 C9 N1 6.49(14) . . . . ?
C11 C8 C9 N1 -175.95(8) . . . . ?
C5 N1 C9 N3 172.14(9) . . . . ?
C1 N1 C9 N3 -7.17(14) . . . . ?
C5 N1 C9 C8 -7.38(14) . . . . ?
C1 N1 C9 C8 173.31(8) . . . . ?
C15 N4 C11 C12 1.06(15) . . . . ?
C15 N4 C11 C8 -178.59(9) . . . . ?
C7 C8 C11 N4 177.04(8) . . . . ?
C9 C8 C11 N4 -0.49(15) . . . . ?
C7 C8 C11 C12 -2.60(15) . . . . ?
C9 C8 C11 C12 179.87(9) . . . . ?
N4 C11 C12 C13 -0.55(16) . . . . ?
C8 C11 C12 C13 179.08(9) . . . . ?
C11 C12 C13 C14 -0.69(16) . . . . ?
C12 C13 C14 C15 1.36(16) . . . . ?
C11 N4 C15 C14 -0.34(16) . . . . ?
C13 C14 C15 N4 -0.89(17) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3

