# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_3181
_database_code_depnum_ccdc_archive 'CCDC 2113802'
loop_
_audit_author_name
_audit_author_address
'Xinghong Zhang'
;China Three Groges Univesity
China
;
_audit_update_record             
;
2021-10-04 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C16 H15 N3'
_chemical_formula_sum            'C16 H15 N3'
_chemical_formula_weight         249.318
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      62
_cell_length_a                   13.6604(3)
_cell_length_b                   6.8744(2)
_cell_length_c                   14.8177(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1391.49(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      73.6690
_cell_measurement_theta_min      4.3740
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       prism
_exptl_crystal_F_000             529.501
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.9978
_diffrn_reflns_Laue_measured_fraction_max 0.9696
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3943
_diffrn_reflns_point_group_measured_fraction_full 0.9978
_diffrn_reflns_point_group_measured_fraction_max 0.9696
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.35
_diffrn_reflns_theta_min         4.40
_diffrn_ambient_temperature      298.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9696
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -33.00   0.50    0.50    --    0.00 -38.00  30.00  108
  2  ω    -14.00  32.00   0.50    0.50    --    0.00 -82.00 -90.00   92
  3  ω      6.00 118.00   0.50    0.98    --   95.80 -61.00 120.00  224
  4  ω      6.00  81.00   0.50    0.98    --   95.80 -30.00 -90.00  150
  5  ω    125.00 150.00   0.50    0.98    --   95.80  82.00 -60.00   50
  6  ω    106.00 184.00   0.50    0.98    --   95.80  61.00  30.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0482451000
_diffrn_orient_matrix_UB_12      0.1942995000
_diffrn_orient_matrix_UB_13      0.0265633000
_diffrn_orient_matrix_UB_21      0.0309823000
_diffrn_orient_matrix_UB_22      -0.0323810000
_diffrn_orient_matrix_UB_23      0.0988876000
_diffrn_orient_matrix_UB_31      0.0970847000
_diffrn_orient_matrix_UB_32      0.1068109000
_diffrn_orient_matrix_UB_33      -0.0182234000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1274
_reflns_number_total             1497
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.1199
_refine_diff_density_min         -0.2873
_refine_diff_density_rms         0.0562
_refine_ls_d_res_high            0.8006
_refine_ls_d_res_low             10.0436
_refine_ls_goodness_of_fit_ref   1.0441
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.0441
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1331
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H10a(0.5) H10b(0.5) H10c(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C12(H12), C11(H11), C4(H4), C2(H2), C3(H3)
3.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C10(H10a,H10b,H10c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
N1 N 0.83967(10) 0.75 0.54053(9) 0.0442(4) Uani 1.000000 2 S T P .
C6 C 0.92901(12) 0.75 0.49321(11) 0.0424(4) Uani 1.000000 2 S T P .
C5 C 0.90938(13) 0.75 0.40175(11) 0.0439(4) Uani 1.000000 2 S T P .
C9 C 0.76219(13) 0.75 0.48389(11) 0.0434(4) Uani 1.000000 2 S T P .
C7 C 0.80020(13) 0.75 0.38664(10) 0.0434(4) Uani 1.000000 2 S T P .
C1 C 1.02346(13) 0.75 0.52732(13) 0.0503(5) Uani 1.000000 2 S T P .
H1 H 1.03541(13) 0.75 0.58910(13) 0.0603(5) Uiso 1.000000 2 RS T P .
C12 C 0.58292(13) 0.75 0.46101(13) 0.0514(5) Uani 1.000000 2 S T P .
H12 H 0.59147(13) 0.75 0.39875(13) 0.0616(6) Uiso 1.000000 2 RS T P .
C11 C 0.66687(13) 0.75 0.51451(12) 0.0508(5) Uani 1.000000 2 S T P .
H11 H 0.65772(13) 0.75 0.57670(12) 0.0610(6) Uiso 1.000000 2 RS T P .
C8 C 0.76897(10) 0.5653(2) 0.33560(8) 0.0556(4) Uani 1.000000 1 . . . .
H8a H 0.8011(6) 0.5614(8) 0.2780(3) 0.0833(6) Uiso 1.000000 1 GR . . .
H8b H 0.7870(6) 0.4526(2) 0.3701(3) 0.0833(6) Uiso 1.000000 1 GR . . .
H8c H 0.69933(13) 0.5667(7) 0.3269(6) 0.0833(6) Uiso 1.000000 1 GR . . .
C13 C 0.48847(14) 0.75 0.49306(14) 0.0535(5) Uani 1.000000 2 S T P .
C4 C 0.98586(14) 0.75 0.34065(13) 0.0564(5) Uani 1.000000 2 S T P .
H4 H 0.97389(14) 0.75 0.27887(13) 0.0677(6) Uiso 1.000000 2 RS T P .
C2 C 1.09909(15) 0.75 0.46537(14) 0.0567(5) Uani 1.000000 2 S T P .
H2 H 1.16343(15) 0.75 0.48588(14) 0.0680(6) Uiso 1.000000 2 RS T P .
C3 C 1.08116(15) 0.75 0.37378(15) 0.0605(5) Uani 1.000000 2 S T P .
H3 H 1.13347(15) 0.75 0.33362(15) 0.0727(7) Uiso 1.000000 2 RS T P .
N3 N 0.34074(14) 0.75 0.38661(16) 0.0920(8) Uani 1.000000 2 S T P .
C10 C 0.83271(17) 0.75 0.63875(12) 0.0618(6) Uani 1.000000 2 S T P .
H10a H 0.7796(8) 0.832(2) 0.65719(13) 0.0927(9) Uiso 0.500000 1 GR . . -1
H10b H 0.8212(13) 0.6198(4) 0.65970(14) 0.0927(9) Uiso 0.500000 1 GR . . -1
H10c H 0.8928(5) 0.798(2) 0.66401(12) 0.0927(9) Uiso 0.500000 1 GR . . -1
C14 C 0.40668(15) 0.75 0.43432(15) 0.0633(6) Uani 1.000000 2 S T P .
C15 C 0.46957(16) 0.75 0.58712(15) 0.0661(6) Uani 1.000000 2 S T P .
N2 N 0.45709(18) 0.75 0.66290(15) 0.1058(9) Uani 1.000000 2 S T P .


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 1.408(2) . ?
N1 C9 1.351(2) . ?
N1 C10 1.458(2) . ?
C6 C5 1.382(2) . ?
C6 C1 1.386(2) . ?
C5 C7 1.508(2) . ?
C5 C4 1.382(3) . ?
C9 C7 1.532(2) . ?
C9 C11 1.379(2) . ?
C7 C8 1.5380(16) 7_575 ?
C7 C8 1.5380(16) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.394(3) . ?
C12 C13 1.375(3) . ?
C11 H11 0.9300 . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C13 C14 1.416(3) . ?
C13 C15 1.417(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.391(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
N3 C14 1.145(3) . ?
C10 H10a 0.9600 . ?
C10 H10a 0.9600 7_575 ?
C10 H10b 0.9600 7_575 ?
C10 H10b 0.9600 . ?
C10 H10c 0.9600 7_575 ?
C10 H10c 0.9600 . ?
C15 N2 1.136(3) . ?

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
C9 N1 C6 111.71(14) . . ?
C10 N1 C6 123.61(15) . . ?
C10 N1 C9 124.68(15) . . ?
C5 C6 N1 108.68(14) . . ?
C1 C6 N1 128.73(16) . . ?
C1 C6 C5 122.58(17) . . ?
C7 C5 C6 109.73(14) . . ?
C4 C5 C6 119.71(17) . . ?
C4 C5 C7 130.56(16) . . ?
C7 C9 N1 108.59(14) . . ?
C11 C9 N1 122.37(15) . . ?
C11 C9 C7 129.03(16) . . ?
C9 C7 C5 101.28(13) . . ?
C8 C7 C5 110.33(10) . . ?
C8 C7 C5 110.33(10) 7_575 . ?
C8 C7 C9 111.62(9) . . ?
C8 C7 C9 111.62(9) 7_575 . ?
C8 C7 C8 111.26(14) 7_575 . ?
H1 C1 C6 121.50(11) . . ?
C2 C1 C6 116.99(17) . . ?
C2 C1 H1 121.50(11) . . ?
C11 C12 H12 117.43(10) . . ?
C13 C12 H12 117.43(12) . . ?
C13 C12 C11 125.14(18) . . ?
C12 C11 C9 126.14(17) . . ?
H11 C11 C9 116.93(10) . . ?
H11 C11 C12 116.93(10) . . ?
H8a C8 C7 109.5 . . ?
H8b C8 C7 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C7 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
C14 C13 C12 121.87(18) . . ?
C15 C13 C12 120.70(18) . . ?
C15 C13 C14 117.43(18) . . ?
H4 C4 C5 120.78(11) . . ?
C3 C4 C5 118.43(18) . . ?
C3 C4 H4 120.78(12) . . ?
H2 C2 C1 119.31(11) . . ?
C3 C2 C1 121.39(18) . . ?
C3 C2 H2 119.31(12) . . ?
C2 C3 C4 120.89(19) . . ?
H3 C3 C4 119.56(12) . . ?
H3 C3 C2 119.56(12) . . ?
H10a C10 N1 109.5 7_575 . ?
H10a C10 N1 109.5 . . ?
H10a C10 H10a 72.2(19) . 7_575 ?
H10b C10 N1 109.5 . . ?
H10b C10 N1 109.5 7_575 . ?
H10b C10 H10a 40.1 . 7_575 ?
H10b C10 H10a 109.5 . . ?
H10b C10 H10a 109.5 7_575 7_575 ?
H10b C10 H10a 40.1 7_575 . ?
H10b C10 H10b 137.5(9) 7_575 . ?
H10c C10 N1 109.5 7_575 . ?
H10c C10 N1 109.5 . . ?
H10c C10 H10a 137.5 7_575 . ?
H10c C10 H10a 137.5 . 7_575 ?
H10c C10 H10a 109.5 7_575 7_575 ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 72.2 7_575 . ?
H10c C10 H10b 109.5 7_575 7_575 ?
H10c C10 H10b 109.5 . . ?
H10c C10 H10b 72.2 . 7_575 ?
H10c C10 H10c 40(2) . 7_575 ?
N3 C14 C13 179.8(2) . . ?
N2 C15 C13 178.1(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
N1 C6 C5 C7 0.0 . . . . ?
N1 C6 C5 C4 180.0 . . . . ?
N1 C6 C1 C2 180.0 . . . . ?
N1 C9 C7 C5 -0.0 . . . . ?
N1 C9 C7 C8 117.39(7) . . . . ?
N1 C9 C7 C8 -117.39(7) . . . 7_575 ?
N1 C9 C11 C12 180.0 . . . . ?
C6 C5 C7 C9 0.0 . . . . ?
C6 C5 C7 C8 -118.33(7) . . . . ?
C6 C5 C7 C8 118.33(7) . . . 7_575 ?
C6 C5 C4 C3 -0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C5 C7 C9 C11 -180.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C9 C11 C12 C13 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.463
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_exp_4455
_database_code_depnum_ccdc_archive 'CCDC 2132410'
loop_
_audit_author_name
_audit_author_address
'Xia Yan'
;China Three Gorges University
China
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2021-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3'
_chemical_formula_sum            'C16 H15 N3'
_chemical_formula_weight         249.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.6221(2)
_cell_length_b                   6.9789(2)
_cell_length_c                   11.5076(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.602(2)
_cell_angle_gamma                90
_cell_volume                     682.74(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8940
_cell_measurement_theta_min      5.1840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3807
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.145
_diffrn_reflns_theta_min         3.896
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  23.00   0.50    0.50    --    0.00 -82.00  30.00   60
  2  ω    -35.00  29.00   0.50    0.50    --    0.00 -77.00 -90.00  128
  3  ω    -28.00   2.00   0.50    0.50    --    0.00 -82.00 120.00   60
  4  ω     79.00 184.00   0.50    0.50    --   95.80  45.00 -90.00  210
  5  ω    121.00 147.00   0.50    0.50    --   95.80  30.00 -30.00   52
  6  ω     23.00  68.00   0.50    0.50    --   95.80 -82.00  90.00   90
  7  ω     73.00 104.00   0.50    0.50    --   95.80 -77.00 -60.00   62
  8  ω     41.00  67.00   0.50    0.50    --   95.80 -77.00 -60.00   52
  9  ω     74.00 100.00   0.50    0.50    --   95.80 -82.00  90.00   52
 10  ω      6.00 124.00   0.50    0.50    --   95.80 -77.00  60.00  236
 11  ω      6.00  98.00   0.50    0.50    --   95.80 -82.00   0.00  184
 12  ω     80.00 105.00   0.50    0.50    --   95.80 -82.00  30.00   50
 13  ω     83.00 175.00   0.50    0.50    --   95.80  30.00-180.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1583140000
_diffrn_orient_matrix_UB_12      0.0842822000
_diffrn_orient_matrix_UB_13      -0.0205198000
_diffrn_orient_matrix_UB_21      -0.0618981000
_diffrn_orient_matrix_UB_22      0.2037003000
_diffrn_orient_matrix_UB_23      0.0162777000
_diffrn_orient_matrix_UB_31      0.0627609000
_diffrn_orient_matrix_UB_32      -0.0119375000
_diffrn_orient_matrix_UB_33      0.1332223000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1331
_reflns_number_total             1466
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.40(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0993P)²+0.0684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H11B(0.5) H11C(0.5)
3.a Me refined with riding coordinates:
 C11(H11A,H11B,H11C)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.29173(14) 0.750000 0.85687(11) 0.0416(4) Uani 1 2 d S T P . .
N2 N 0.1073(3) 0.750000 0.22644(15) 0.1051(10) Uani 1 2 d S T P . .
N3 N -0.2268(2) 0.750000 0.47606(18) 0.0744(6) Uani 1 2 d S T P . .
C1 C 0.55490(17) 0.750000 0.85756(13) 0.0414(4) Uani 1 2 d S T P . .
C2 C 0.52431(14) 0.5674(2) 0.66831(10) 0.0541(4) Uani 1 1 d . . . . .
H2A H 0.636563 0.562369 0.673810 0.081 Uiso 1 1 calc R U . . .
H2B H 0.476011 0.569541 0.586875 0.081 Uiso 1 1 calc R U . . .
H2C H 0.488933 0.456625 0.705869 0.081 Uiso 1 1 calc R U . . .
C3 C 0.6371(2) 0.750000 1.09901(15) 0.0546(5) Uani 1 2 d S T P . .
H3 H 0.666508 0.750000 1.180523 0.065 Uiso 1 2 calc R U P . .
C4 C 0.44083(17) 0.750000 0.92919(13) 0.0393(4) Uani 1 2 d S T P . .
C5 C -0.0991(2) 0.750000 0.45937(15) 0.0504(5) Uani 1 2 d S T P . .
C6 C 0.30405(18) 0.750000 0.74107(13) 0.0407(4) Uani 1 2 d S T P . .
C7 C 0.0852(2) 0.750000 0.32202(17) 0.0666(6) Uani 1 2 d S T P . .
C8 C 0.47840(17) 0.750000 0.72993(12) 0.0420(4) Uani 1 2 d S T P . .
C9 C 0.1839(2) 0.750000 0.53256(14) 0.0498(5) Uani 1 2 d S T P . .
H9 H 0.284232 0.750000 0.512807 0.060 Uiso 1 2 calc R U P . .
C10 C 0.17458(19) 0.750000 0.65250(14) 0.0466(5) Uani 1 2 d S T P . .
H10 H 0.075273 0.750000 0.673990 0.056 Uiso 1 2 calc R U P . .
C11 C 0.1446(2) 0.750000 0.90245(16) 0.0560(5) Uani 1 2 d S T P . .
H11A H 0.166188 0.750000 0.987033 0.084 Uiso 0.5 1 calc R U P A -1
H11B H 0.085181 0.862315 0.875236 0.084 Uiso 0.5 1 calc R U P A -1
H11C H 0.085180 0.637685 0.875235 0.084 Uiso 0.5 1 calc R U P A -1
C12 C 0.4784(2) 0.750000 1.05076(13) 0.0478(5) Uani 1 2 d S T P . .
H12 H 0.400861 0.750000 1.098078 0.057 Uiso 1 2 calc R U P . .
C13 C 0.7522(2) 0.750000 1.02890(16) 0.0573(5) Uani 1 2 d S T P . .
H13 H 0.857706 0.750000 1.063566 0.069 Uiso 1 2 calc R U P . .
C14 C 0.0591(2) 0.750000 0.44052(14) 0.0494(5) Uani 1 2 d S T P . .
C15 C 0.71176(19) 0.750000 0.90704(16) 0.0535(5) Uani 1 2 d S T P . .
H15 H 0.789178 0.750000 0.859617 0.064 Uiso 1 2 calc R U P . .


_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 C4 1.4101(19) . ?
N1 C6 1.3543(19) . ?
N1 C11 1.4512(19) . ?
N2 C7 1.147(3) . ?
N3 C5 1.149(3) . ?
C1 C4 1.385(2) . ?
C1 C8 1.506(2) . ?
C1 C15 1.377(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C8 1.5418(15) . ?
C3 H3 0.9300 . ?
C3 C12 1.388(3) . ?
C3 C13 1.380(3) . ?
C4 C12 1.382(2) . ?
C5 C14 1.416(2) . ?
C6 C8 1.530(2) . ?
C6 C10 1.380(2) . ?
C7 C14 1.419(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.396(2) . ?
C9 C14 1.379(2) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C15 1.388(2) . ?
C15 H15 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
C4 N1 C11 123.53(13) . . ?
C6 N1 C4 111.55(12) . . ?
C6 N1 C11 124.91(13) . . ?
C4 C1 C8 109.97(13) . . ?
C15 C1 C4 120.00(15) . . ?
C15 C1 C8 130.03(15) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C2 H2A 109.5 . . ?
C8 C2 H2B 109.5 . . ?
C8 C2 H2C 109.5 . . ?
C12 C3 H3 119.2 . . ?
C13 C3 H3 119.2 . . ?
C13 C3 C12 121.57(15) . . ?
C1 C4 N1 108.47(13) . . ?
C12 C4 N1 129.34(14) . . ?
C12 C4 C1 122.19(14) . . ?
N3 C5 C14 179.20(19) . . ?
N1 C6 C8 108.77(12) . . ?
N1 C6 C10 122.69(14) . . ?
C10 C6 C8 128.54(14) . . ?
N2 C7 C14 179.6(2) . . ?
C1 C8 C2 110.13(8) . 4_575 ?
C1 C8 C2 110.13(8) . . ?
C1 C8 C6 101.24(11) . . ?
C2 C8 C2 111.49(13) 4_575 . ?
C6 C8 C2 111.70(8) . 4_575 ?
C6 C8 C2 111.70(8) . . ?
C10 C9 H9 116.8 . . ?
C14 C9 H9 116.8 . . ?
C14 C9 C10 126.37(17) . . ?
C6 C10 C9 123.85(16) . . ?
C6 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12 121.5 . . ?
C4 C12 C3 116.98(15) . . ?
C4 C12 H12 121.5 . . ?
C3 C13 H13 119.8 . . ?
C3 C13 C15 120.44(16) . . ?
C15 C13 H13 119.8 . . ?
C5 C14 C7 117.30(15) . . ?
C9 C14 C5 122.07(16) . . ?
C9 C14 C7 120.63(17) . . ?
C1 C15 C13 118.82(16) . . ?
C1 C15 H15 120.6 . . ?
C13 C15 H15 120.6 . . ?

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
N1 C4 C12 C3 180.000(1) . . . . ?
N1 C6 C8 C1 0.000(1) . . . . ?
N1 C6 C8 C2 117.18(9) . . . . ?
N1 C6 C8 C2 -117.18(9) . . . 4_575 ?
N1 C6 C10 C9 180.000(1) . . . . ?
C1 C4 C12 C3 0.000(1) . . . . ?
C3 C13 C15 C1 0.000(1) . . . . ?
C4 N1 C6 C8 0.000(1) . . . . ?
C4 N1 C6 C10 180.000(1) . . . . ?
C4 C1 C8 C2 118.32(9) . . . 4_575 ?
C4 C1 C8 C2 -118.32(9) . . . . ?
C4 C1 C8 C6 0.000(1) . . . . ?
C4 C1 C15 C13 0.000(1) . . . . ?
C6 N1 C4 C1 0.000(1) . . . . ?
C6 N1 C4 C12 180.000(1) . . . . ?
C8 C1 C4 N1 0.000(1) . . . . ?
C8 C1 C4 C12 180.000(1) . . . . ?
C8 C1 C15 C13 180.000(1) . . . . ?
C8 C6 C10 C9 0.000(1) . . . . ?
C10 C6 C8 C1 180.000(1) . . . . ?
C10 C6 C8 C2 62.82(9) . . . 4_575 ?
C10 C6 C8 C2 -62.82(9) . . . . ?
C10 C9 C14 C5 0.000(1) . . . . ?
C10 C9 C14 C7 180.000(0) . . . . ?
C11 N1 C4 C1 180.000(1) . . . . ?
C11 N1 C4 C12 0.000(1) . . . . ?
C11 N1 C6 C8 180.000(0) . . . . ?
C11 N1 C6 C10 0.000(1) . . . . ?
C12 C3 C13 C15 0.000(1) . . . . ?
C13 C3 C12 C4 0.000(1) . . . . ?
C14 C9 C10 C6 180.000(0) . . . . ?
C15 C1 C4 N1 180.000(1) . . . . ?
C15 C1 C4 C12 0.000(1) . . . . ?
C15 C1 C8 C2 61.68(9) . . . . ?
C15 C1 C8 C2 -61.68(9) . . . 4_575 ?
C15 C1 C8 C6 180.000(1) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.033
_oxdiff_exptl_absorpt_empirical_full_min 0.445
####################################################################### 
# 
# 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_exp_3015
_database_code_depnum_ccdc_archive 'CCDC 2113793'
loop_
_audit_author_name
_audit_author_address
'Shuzhang Xiao'
;China Three Gorges University
China
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3'
_chemical_formula_sum            'C16 H15 N3'
_chemical_formula_weight         249.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   13.6543(4)
_cell_length_b                   6.8710(2)
_cell_length_c                   14.8159(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1390.01(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7205
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1760
_cell_measurement_theta_min      7.1550
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13710
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.227
_diffrn_reflns_theta_min         4.404
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  28.00   0.50    0.50    --    0.00 -77.00-120.00   56
  2  ω    -17.00  13.00   0.50    0.50    --    0.00 -82.00 -60.00   60
  3  ω    -12.00  31.00   0.50    0.50    --    0.00 -82.00  90.00   86
  4  ω    -27.00  17.00   0.50    0.50    --    0.00 -82.00-180.00   88
  5  ω    -43.00  -3.00   0.50    0.50    --    0.00 -77.00-120.00   80
  6  ω    -30.00  -4.00   0.50    0.50    --    0.00 -82.00   0.00   52
  7  ω      6.00  32.00   0.50    0.50    --    0.00 -82.00   0.00   52
  8  ω     48.00 128.00   0.50    0.50    --   95.80 -82.00 -90.00  160
  9  ω     76.00 178.00   0.50    0.50    --   95.80  30.00  60.00  204
 10  ω     77.00 184.00   0.50    0.50    --   95.80  30.00   0.00  214
 11  ω    132.00 157.00   0.50    0.50    --   95.80  82.00 150.00   50
 12  ω     48.00 114.00   0.50    0.50    --   95.80 -30.00 -30.00  132
 13  ω      8.00  33.00   0.50    0.50    --   95.80 -82.00 -30.00   50
 14  ω     58.00  83.00   0.50    0.50    --   95.80 -82.00 -30.00   50
 15  ω     73.00 118.00   0.50    0.50    --   95.80 -82.00   0.00   90
 16  ω    143.00 169.00   0.50    0.50    --   95.80  45.00 -90.00   52
 17  ω     76.00 103.00   0.50    0.50    --   95.80  45.00 -90.00   54
 18  ω     94.00 126.00   0.50    0.50    --   95.80 -82.00-180.00   64
 19  ω      8.00 120.00   0.50    0.50    --   95.80 -61.00 120.00  224
 20  ω      6.00  51.00   0.50    0.50    --   95.80 -82.00-180.00   90
 21  ω     95.00 121.00   0.50    0.50    --   95.80 -82.00 -30.00   52
 22  ω      6.00 126.00   0.50    0.50    --   95.80 -82.00 120.00  240
 23  ω      7.00 114.00   0.50    0.50    --   95.80 -45.00-120.00  214
 24  ω     72.00 149.00   0.50    0.50    --   95.80  61.00 -30.00  154
 25  ω     82.00 107.00   0.50    0.50    --   95.80 -82.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1056698000
_diffrn_orient_matrix_UB_12      -0.0614193000
_diffrn_orient_matrix_UB_13      0.0229565000
_diffrn_orient_matrix_UB_21      0.0139044000
_diffrn_orient_matrix_UB_22      0.0743005000
_diffrn_orient_matrix_UB_23      0.0972075000
_diffrn_orient_matrix_UB_31      -0.0371044000
_diffrn_orient_matrix_UB_32      0.2024663000
_diffrn_orient_matrix_UB_33      -0.0287614000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1409
_reflns_number_total             1527
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0683
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0893P)²+0.2800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1585
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H15B(0.5) H15C(0.5)
3.a Me refined with riding coordinates:
 C15(H15A,H15B,H15C)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.4565(2) 0.2500 0.33721(16) 0.1014(10) Uani 1 2 d S T P . .
N2 N 0.34068(15) 0.2500 0.61369(16) 0.0868(8) Uani 1 2 d S T P . .
N3 N 0.83960(11) 0.2500 0.45961(10) 0.0411(4) Uani 1 2 d S T P . .
C1 C 0.46920(16) 0.2500 0.41304(16) 0.0627(6) Uani 1 2 d S T P . .
C2 C 0.48848(14) 0.2500 0.50730(15) 0.0504(5) Uani 1 2 d S T P . .
C3 C 0.40655(16) 0.2500 0.56584(16) 0.0597(6) Uani 1 2 d S T P . .
C4 C 0.58294(14) 0.2500 0.53917(14) 0.0479(5) Uani 1 2 d S T P . .
H4 H 0.5916 0.2500 0.6014 0.058 Uiso 1 2 calc RS T P . .
C5 C 0.66685(14) 0.2500 0.48568(13) 0.0476(5) Uani 1 2 d S T P . .
H5 H 0.6576 0.2500 0.4235 0.057 Uiso 1 2 calc RS T P . .
C6 C 0.76227(13) 0.2500 0.51595(11) 0.0400(4) Uani 1 2 d S T P . .
C7 C 0.80006(13) 0.2500 0.61333(11) 0.0399(4) Uani 1 2 d S T P . .
C8 C 0.76892(10) 0.4348(2) 0.66440(9) 0.0519(4) Uani 1 1 d . . . . .
H8A H 0.8012 0.4387 0.7219 0.078 Uiso 1 1 calc GR . . . .
H8B H 0.6993 0.4334 0.6733 0.078 Uiso 1 1 calc GR . . . .
H8C H 0.7868 0.5475 0.6299 0.078 Uiso 1 1 calc GR . . . .
C9 C 0.90947(13) 0.2500 0.59848(12) 0.0408(4) Uani 1 2 d S T P . .
C10 C 0.98596(15) 0.2500 0.65932(14) 0.0531(5) Uani 1 2 d S T P . .
H10 H 0.9739 0.2500 0.7211 0.064 Uiso 1 2 calc RS T P . .
C11 C 1.08151(15) 0.2500 0.62643(16) 0.0568(6) Uani 1 2 d S T P . .
H11 H 1.1338 0.2500 0.6666 0.068 Uiso 1 2 calc RS T P . .
C12 C 1.09922(15) 0.2500 0.53459(15) 0.0529(5) Uani 1 2 d S T P . .
H12 H 1.1636 0.2500 0.5140 0.064 Uiso 1 2 calc RS T P . .
C13 C 1.02359(14) 0.2500 0.47257(14) 0.0469(5) Uani 1 2 d S T P . .
H13 H 1.0356 0.2500 0.4108 0.056 Uiso 1 2 calc RS T P . .
C14 C 0.92912(12) 0.2500 0.50652(12) 0.0385(4) Uani 1 2 d S T P . .
C15 C 0.83282(17) 0.2500 0.36127(13) 0.0572(6) Uani 1 2 d S T P . .
H15A H 0.8975 0.2500 0.3358 0.086 Uiso 0.5 1 calc RS T P A -1
H15B H 0.7983 0.1359 0.3416 0.086 Uiso 0.5 1 calc R . . A -1
H15C H 0.7983 0.3641 0.3416 0.086 Uiso 0.5 1 calc R . . A -1


_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 1.137(3) . ?
N2 C3 1.145(3) . ?
N3 C6 1.346(2) . ?
N3 C14 1.406(2) . ?
N3 C15 1.460(2) . ?
C1 C2 1.421(3) . ?
C2 C3 1.416(3) . ?
C2 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(3) . ?
C6 C7 1.532(2) . ?
C7 C8 1.5379(16) 7_565 ?
C7 C8 1.5379(16) . ?
C7 C9 1.510(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.380(3) . ?
C9 C14 1.389(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C6 N3 C14 112.05(14) . . ?
C6 N3 C15 124.69(16) . . ?
C14 N3 C15 123.26(15) . . ?
N1 C1 C2 178.1(3) . . ?
C3 C2 C1 117.11(19) . . ?
C4 C2 C1 120.78(19) . . ?
C4 C2 C3 122.1(2) . . ?
N2 C3 C2 179.5(2) . . ?
C2 C4 H4 117.4 . . ?
C2 C4 C5 125.22(19) . . ?
C5 C4 H4 117.4 . . ?
C4 C5 H5 116.8 . . ?
C6 C5 C4 126.33(18) . . ?
C6 C5 H5 116.8 . . ?
N3 C6 C5 122.67(16) . . ?
N3 C6 C7 108.64(15) . . ?
C5 C6 C7 128.68(16) . . ?
C6 C7 C8 111.72(10) . . ?
C6 C7 C8 111.72(10) . 7_565 ?
C8 C7 C8 111.28(15) 7_565 . ?
C9 C7 C6 101.31(13) . . ?
C9 C7 C8 110.20(10) . 7_565 ?
C9 C7 C8 110.20(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 130.82(17) . . ?
C10 C9 C14 119.66(17) . . ?
C14 C9 C7 109.52(15) . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.72(19) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.55(19) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.59(19) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.5 . . ?
C12 C13 C14 117.03(18) . . ?
C14 C13 H13 121.5 . . ?
C9 C14 N3 108.48(15) . . ?
C13 C14 N3 129.08(17) . . ?
C13 C14 C9 122.44(17) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
N3 C6 C7 C8 -117.30(11) . . . 7_565 ?
N3 C6 C7 C8 117.30(11) . . . . ?
N3 C6 C7 C9 0.000(0) . . . . ?
C1 C2 C4 C5 0.000(0) . . . . ?
C2 C4 C5 C6 180.000(0) . . . . ?
C3 C2 C4 C5 180.000(0) . . . . ?
C4 C5 C6 N3 180.000(0) . . . . ?
C4 C5 C6 C7 0.000(0) . . . . ?
C5 C6 C7 C8 62.70(11) . . . 7_565 ?
C5 C6 C7 C8 -62.70(11) . . . . ?
C5 C6 C7 C9 180.000(0) . . . . ?
C6 N3 C14 C9 0.000(0) . . . . ?
C6 N3 C14 C13 180.000(0) . . . . ?
C6 C7 C9 C10 180.000(0) . . . . ?
C6 C7 C9 C14 0.000(0) . . . . ?
C7 C9 C10 C11 180.000(0) . . . . ?
C7 C9 C14 N3 0.000(0) . . . . ?
C7 C9 C14 C13 180.000(0) . . . . ?
C8 C7 C9 C10 -61.60(10) 7_565 . . . ?
C8 C7 C9 C10 61.60(10) . . . . ?
C8 C7 C9 C14 -118.40(10) . . . . ?
C8 C7 C9 C14 118.40(10) 7_565 . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C10 C9 C14 N3 180.000(0) . . . . ?
C10 C9 C14 C13 0.000(0) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
C11 C12 C13 C14 0.000(0) . . . . ?
C12 C13 C14 N3 180.000(0) . . . . ?
C12 C13 C14 C9 0.000(0) . . . . ?
C14 N3 C6 C5 180.000(0) . . . . ?
C14 N3 C6 C7 0.000(0) . . . . ?
C14 C9 C10 C11 0.000(1) . . . . ?
C15 N3 C6 C5 0.000(0) . . . . ?
C15 N3 C6 C7 180.000(0) . . . . ?
C15 N3 C14 C9 180.000(0) . . . . ?
C15 N3 C14 C13 0.000(0) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.284
_oxdiff_exptl_absorpt_empirical_full_min 0.372
