# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_Compound3a
_database_code_depnum_ccdc_archive 'CCDC 1914063'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            aminopyrimidine.toluene
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N3, C7 H8'
_chemical_formula_sum            'C30 H27 N3'
_chemical_formula_weight         429.55

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

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                   14.9290(3)
_cell_length_b                   5.74297(8)
_cell_length_c                   27.7627(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.7847(18)
_cell_angle_gamma                90.00
_cell_volume                     2301.47(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6977
_cell_measurement_theta_min      5.0750
_cell_measurement_theta_max      73.7820

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8863
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14159
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         69.96
_reflns_number_total             4326
_reflns_number_gt                3961
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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. 
;

# start Validation Reply Form
_vrf_PLAT420_Compound3a          
;
PROBLEM: D-H Without Acceptor       N1-- H1B      .     Please Check   
RESPONSE: One of hydrogen atom of the amine group was defined to point to the
N3a atom on the adjacent symmetrical 5-benzyl-2,6-diphenyl-4-aminopyrimidine 
molecule,forming an intermolecular hydrogen bonding N1-H1A....N3A. Thus, the 
other hydrogen atom H1B was defined to point to the phenyl ring of the benzyl
group with the bond angle of H1A-N1-H1B being 120 degree.
;

# end Validation Reply Form

_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)+(0.0557P)²+0.5350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4326
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
N1 N 0.09252(7) 0.79781(18) 0.00277(4) 0.0275(2) Uani 1 1 d . . .
H1A H 0.0555 0.9065 -0.0136 0.033 Uiso 1 1 calc R . .
H1B H 0.1440 0.7631 -0.0056 0.033 Uiso 1 1 calc R . .
N2 N 0.02045(6) 0.45909(16) 0.11672(3) 0.0211(2) Uani 1 1 d . . .
N3 N -0.00893(6) 0.74423(16) 0.05196(3) 0.0213(2) Uani 1 1 d . . .
C1 C 0.07040(7) 0.68383(19) 0.04089(4) 0.0211(2) Uani 1 1 d . . .
C2 C 0.12867(7) 0.50405(19) 0.06654(4) 0.0201(2) Uani 1 1 d . . .
C3 C 0.20792(7) 0.41866(19) 0.04678(4) 0.0215(2) Uani 1 1 d . . .
H3A H 0.1826 0.3703 0.0117 0.026 Uiso 1 1 calc R . .
H3B H 0.2342 0.2781 0.0659 0.026 Uiso 1 1 calc R . .
C4 C 0.28661(7) 0.5890(2) 0.04854(4) 0.0220(2) Uani 1 1 d . . .
C5 C 0.30405(8) 0.7777(2) 0.08101(4) 0.0238(2) Uani 1 1 d . . .
H5A H 0.2657 0.8033 0.1031 0.029 Uiso 1 1 calc R . .
C6 C 0.37687(8) 0.9292(2) 0.08157(5) 0.0294(3) Uani 1 1 d . . .
H6A H 0.3882 1.0570 0.1040 0.035 Uiso 1 1 calc R . .
C7 C 0.43301(9) 0.8943(2) 0.04947(5) 0.0343(3) Uani 1 1 d . . .
H7A H 0.4829 0.9977 0.0499 0.041 Uiso 1 1 calc R . .
C8 C 0.41605(9) 0.7076(2) 0.01678(5) 0.0360(3) Uani 1 1 d . . .
H8A H 0.4543 0.6834 -0.0053 0.043 Uiso 1 1 calc R . .
C9 C 0.34359(9) 0.5562(2) 0.01619(5) 0.0297(3) Uani 1 1 d . . .
H9A H 0.3325 0.4289 -0.0064 0.036 Uiso 1 1 calc R . .
C10 C 0.10222(7) 0.40615(18) 0.10642(4) 0.0201(2) Uani 1 1 d . . .
C11 C 0.15984(7) 0.23449(19) 0.14105(4) 0.0202(2) Uani 1 1 d . . .
C12 C 0.11811(8) 0.0397(2) 0.15625(4) 0.0230(2) Uani 1 1 d . . .
H12A H 0.0534 0.0160 0.1437 0.028 Uiso 1 1 calc R . .
C13 C 0.17016(8) -0.1192(2) 0.18933(4) 0.0257(2) Uani 1 1 d . . .
H13A H 0.1412 -0.2523 0.1990 0.031 Uiso 1 1 calc R . .
C14 C 0.26477(8) -0.0845(2) 0.20855(4) 0.0256(2) Uani 1 1 d . . .
H14A H 0.3004 -0.1934 0.2313 0.031 Uiso 1 1 calc R . .
C15 C 0.30674(8) 0.1100(2) 0.19429(4) 0.0241(2) Uani 1 1 d . . .
H15A H 0.3712 0.1350 0.2076 0.029 Uiso 1 1 calc R . .
C16 C 0.25500(8) 0.26831(19) 0.16070(4) 0.0218(2) Uani 1 1 d . . .
H16A H 0.2844 0.4006 0.1510 0.026 Uiso 1 1 calc R . .
C17 C -0.03132(7) 0.61989(19) 0.08833(4) 0.0203(2) Uani 1 1 d . . .
C18 C -0.12392(7) 0.6644(2) 0.09761(4) 0.0221(2) Uani 1 1 d . . .
C19 C -0.17128(9) 0.8721(2) 0.08355(5) 0.0296(3) Uani 1 1 d . . .
H19A H -0.1432 0.9922 0.0689 0.035 Uiso 1 1 calc R . .
C20 C -0.25925(9) 0.9058(2) 0.09067(5) 0.0341(3) Uani 1 1 d . . .
H20A H -0.2910 1.0483 0.0808 0.041 Uiso 1 1 calc R . .
C21 C -0.30075(8) 0.7322(2) 0.11209(5) 0.0318(3) Uani 1 1 d . . .
H21A H -0.3613 0.7540 0.1165 0.038 Uiso 1 1 calc R . .
C22 C -0.25340(9) 0.5272(2) 0.12706(5) 0.0330(3) Uani 1 1 d . . .
H22A H -0.2812 0.4087 0.1422 0.040 Uiso 1 1 calc R . .
C23 C -0.16543(8) 0.4930(2) 0.12009(5) 0.0284(3) Uani 1 1 d . . .
H23A H -0.1334 0.3517 0.1307 0.034 Uiso 1 1 calc R . .
C24 C 0.66878(11) 0.0193(3) 0.23544(7) 0.0490(4) Uani 1 1 d . . .
H24A H 0.6905 0.0074 0.2718 0.074 Uiso 1 1 calc R . .
H24B H 0.7216 0.0487 0.2214 0.074 Uiso 1 1 calc R . .
H24C H 0.6386 -0.1267 0.2219 0.074 Uiso 1 1 calc R . .
C25 C 0.60061(9) 0.2165(2) 0.22199(5) 0.0350(3) Uani 1 1 d . . .
C26 C 0.57768(10) 0.3536(3) 0.25833(5) 0.0402(3) Uani 1 1 d . . .
H26A H 0.6040 0.3194 0.2925 0.048 Uiso 1 1 calc R . .
C27 C 0.51703(10) 0.5396(3) 0.24548(6) 0.0421(3) Uani 1 1 d . . .
H27A H 0.5019 0.6312 0.2708 0.051 Uiso 1 1 calc R . .
C28 C 0.47856(9) 0.5920(3) 0.19581(6) 0.0389(3) Uani 1 1 d . . .
H28A H 0.4378 0.7209 0.1869 0.047 Uiso 1 1 calc R . .
C29 C 0.49983(9) 0.4556(3) 0.15929(5) 0.0356(3) Uani 1 1 d . . .
H29A H 0.4731 0.4897 0.1252 0.043 Uiso 1 1 calc R . .
C30 C 0.55995(8) 0.2694(2) 0.17230(5) 0.0331(3) Uani 1 1 d . . .
H30A H 0.5737 0.1761 0.1469 0.040 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
N1 C1 1.3551(15) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C17 1.3268(15) . ?
N2 C10 1.3575(14) . ?
N3 C1 1.3428(14) . ?
N3 C17 1.3466(15) . ?
C1 C2 1.4190(15) . ?
C2 C10 1.3860(15) . ?
C2 C3 1.5074(15) . ?
C3 C4 1.5199(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.3909(17) . ?
C4 C9 1.3984(16) . ?
C5 C6 1.3895(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3850(18) . ?
C6 H6A 0.9500 . ?
C7 C8 1.385(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3847(19) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.4879(15) . ?
C11 C12 1.3973(16) . ?
C11 C16 1.3993(16) . ?
C12 C13 1.3838(16) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3909(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3868(17) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3873(16) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.4914(15) . ?
C18 C19 1.3907(17) . ?
C18 C23 1.3928(17) . ?
C19 C20 1.3906(17) . ?
C19 H19A 0.9500 . ?
C20 C21 1.386(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.381(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3893(17) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 C25 1.505(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.390(2) . ?
C25 C30 1.392(2) . ?
C26 C27 1.387(2) . ?
C26 H26A 0.9500 . ?
C27 C28 1.385(2) . ?
C27 H27A 0.9500 . ?
C28 C29 1.381(2) . ?
C28 H28A 0.9500 . ?
C29 C30 1.384(2) . ?
C29 H29A 0.9500 . ?
C30 H30A 0.9500 . ?

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
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C17 N2 C10 116.72(9) . . ?
C1 N3 C17 115.90(9) . . ?
N3 C1 N1 117.32(10) . . ?
N3 C1 C2 122.46(10) . . ?
N1 C1 C2 120.19(10) . . ?
C10 C2 C1 115.64(10) . . ?
C10 C2 C3 124.66(10) . . ?
C1 C2 C3 119.46(10) . . ?
C2 C3 C4 116.80(9) . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3B 108.1 . . ?
C4 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
C5 C4 C9 118.49(11) . . ?
C5 C4 C3 122.52(10) . . ?
C9 C4 C3 118.98(11) . . ?
C6 C5 C4 120.77(11) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C7 C6 C5 120.15(12) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C8 119.61(12) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C9 C8 C7 120.35(12) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C4 120.62(12) . . ?
C8 C9 H9A 119.7 . . ?
C4 C9 H9A 119.7 . . ?
N2 C10 C2 122.16(10) . . ?
N2 C10 C11 114.52(9) . . ?
C2 C10 C11 123.32(10) . . ?
C12 C11 C16 118.68(10) . . ?
C12 C11 C10 119.80(10) . . ?
C16 C11 C10 121.47(10) . . ?
C13 C12 C11 120.67(10) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 120.22(10) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C15 C14 C13 119.63(10) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 120.33(10) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 120.45(10) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
N2 C17 N3 126.59(10) . . ?
N2 C17 C18 116.22(9) . . ?
N3 C17 C18 117.19(10) . . ?
C19 C18 C23 118.64(10) . . ?
C19 C18 C17 121.72(10) . . ?
C23 C18 C17 119.63(10) . . ?
C20 C19 C18 120.71(12) . . ?
C20 C19 H19A 119.6 . . ?
C18 C19 H19A 119.6 . . ?
C21 C20 C19 120.18(12) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C22 C21 C20 119.45(11) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
C21 C22 C23 120.54(12) . . ?
C21 C22 H22A 119.7 . . ?
C23 C22 H22A 119.7 . . ?
C22 C23 C18 120.46(11) . . ?
C22 C23 H23A 119.8 . . ?
C18 C23 H23A 119.8 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 118.04(13) . . ?
C26 C25 C24 121.50(14) . . ?
C30 C25 C24 120.45(14) . . ?
C27 C26 C25 121.00(13) . . ?
C27 C26 H26A 119.5 . . ?
C25 C26 H26A 119.5 . . ?
C28 C27 C26 120.08(14) . . ?
C28 C27 H27A 120.0 . . ?
C26 C27 H27A 120.0 . . ?
C29 C28 C27 119.56(13) . . ?
C29 C28 H28A 120.2 . . ?
C27 C28 H28A 120.2 . . ?
C28 C29 C30 120.14(13) . . ?
C28 C29 H29A 119.9 . . ?
C30 C29 H29A 119.9 . . ?
C29 C30 C25 121.16(13) . . ?
C29 C30 H30A 119.4 . . ?
C25 C30 H30A 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        69.96
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_Compound4aa
_database_code_depnum_ccdc_archive 'CCDC 1936385'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2'
_chemical_formula_sum            'C17 H16 N2'
_chemical_formula_weight         248.32

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5340(13)
_cell_length_b                   6.2910(3)
_cell_length_c                   15.0837(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.849(9)
_cell_angle_gamma                90.00
_cell_volume                     1348.18(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5142
_cell_measurement_theta_min      4.2960
_cell_measurement_theta_max      29.5300

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13846
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         26.50
_reflns_number_total             2779
_reflns_number_gt                2382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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. 
;


# start Validation Reply Form
_vrf_PLAT420_Compound4aa         
;
PROBLEM:  D-H Without Acceptor       N2 --H2A      ....  Please Check 
RESPONSE: The hydrogen atom of H2B rided on the amine nitrogen atom was set 
pointed to the CN group on the neighbour molecule to form an intermolecular
hydrogen bond. Thus the direction of H2A was restrained in term of the bond
length and bond angle of amine (R-NH2) group. 
;

# end Validation Reply Form

_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)+(0.0355P)²+1.2100P] 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         2779
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
N1 N 0.21831(10) 0.6607(2) 0.65608(9) 0.0211(3) Uani 1 1 d . . .
N2 N 0.27028(10) 0.6969(2) 0.36428(10) 0.0260(3) Uani 1 1 d . . .
H2A H 0.3203 0.6181 0.3749 0.031 Uiso 1 1 calc R . .
H2B H 0.2438 0.7679 0.3096 0.031 Uiso 1 1 calc R . .
C1 C 0.23928(10) 0.6389(2) 0.59162(11) 0.0162(3) Uani 1 1 d . . .
C2 C 0.27262(11) 0.6015(2) 0.51786(11) 0.0174(3) Uani 1 1 d . . .
C3 C 0.35712(11) 0.4558(2) 0.54606(11) 0.0187(3) Uani 1 1 d . . .
H3A H 0.3589 0.3943 0.4864 0.022 Uiso 1 1 calc R . .
H3B H 0.3491 0.3371 0.5852 0.022 Uiso 1 1 calc R . .
C4 C 0.45080(11) 0.5642(2) 0.60345(11) 0.0174(3) Uani 1 1 d . . .
C5 C 0.46886(12) 0.7702(3) 0.58086(11) 0.0204(3) Uani 1 1 d . . .
H5A H 0.4211 0.8458 0.5301 0.024 Uiso 1 1 calc R . .
C6 C 0.55549(12) 0.8660(3) 0.63143(12) 0.0232(4) Uani 1 1 d . . .
H6A H 0.5670 1.0053 0.6145 0.028 Uiso 1 1 calc R . .
C7 C 0.62532(12) 0.7589(3) 0.70659(12) 0.0229(4) Uani 1 1 d . . .
H7A H 0.6849 0.8237 0.7407 0.028 Uiso 1 1 calc R . .
C8 C 0.60756(11) 0.5563(3) 0.73162(12) 0.0220(4) Uani 1 1 d . . .
H8A H 0.6546 0.4837 0.7842 0.026 Uiso 1 1 calc R . .
C9 C 0.52118(11) 0.4593(3) 0.68001(11) 0.0193(3) Uani 1 1 d . . .
H9A H 0.5100 0.3199 0.6971 0.023 Uiso 1 1 calc R . .
C10 C 0.23401(11) 0.7088(3) 0.43214(11) 0.0185(3) Uani 1 1 d . . .
C11 C 0.15186(11) 0.8532(2) 0.40677(10) 0.0178(3) Uani 1 1 d . . .
C12 C 0.15721(12) 1.0593(3) 0.37533(11) 0.0213(3) Uani 1 1 d . . .
H12A H 0.2136 1.1078 0.3717 0.026 Uiso 1 1 calc R . .
C13 C 0.08009(12) 1.1931(3) 0.34934(11) 0.0234(4) Uani 1 1 d . . .
H13A H 0.0840 1.3343 0.3290 0.028 Uiso 1 1 calc R . .
C14 C -0.00291(11) 1.1217(3) 0.35297(11) 0.0218(4) Uani 1 1 d . . .
H14A H -0.0555 1.2146 0.3347 0.026 Uiso 1 1 calc R . .
C15 C -0.01032(11) 0.9154(3) 0.38297(11) 0.0198(3) Uani 1 1 d . . .
C16 C 0.06822(11) 0.7833(2) 0.41073(10) 0.0180(3) Uani 1 1 d . . .
H16A H 0.0648 0.6434 0.4327 0.022 Uiso 1 1 calc R . .
C17 C -0.10169(12) 0.8340(3) 0.38260(13) 0.0264(4) Uani 1 1 d . . .
H17A H -0.0933 0.6871 0.4062 0.040 Uiso 1 1 calc R . .
H17B H -0.1505 0.8387 0.3164 0.040 Uiso 1 1 calc R . .
H17C H -0.1206 0.9232 0.4249 0.040 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
N1 C1 1.152(2) . ?
N2 C10 1.355(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.424(2) . ?
C2 C10 1.364(2) . ?
C2 C3 1.514(2) . ?
C3 C4 1.521(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.394(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.388(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.389(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.391(2) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.485(2) . ?
C11 C12 1.395(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.385(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.387(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.394(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.393(2) . ?
C15 C17 1.507(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 174.69(16) . . ?
C10 C2 C1 119.96(14) . . ?
C10 C2 C3 124.39(14) . . ?
C1 C2 C3 115.38(13) . . ?
C2 C3 C4 114.20(13) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C9 C4 C5 118.28(15) . . ?
C9 C4 C3 120.57(14) . . ?
C5 C4 C3 121.16(14) . . ?
C6 C5 C4 120.97(15) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C7 C6 C5 120.19(15) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C8 119.52(15) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C7 C8 C9 120.22(15) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C8 C9 C4 120.79(15) . . ?
C8 C9 H9A 119.6 . . ?
C4 C9 H9A 119.6 . . ?
N2 C10 C2 122.07(15) . . ?
N2 C10 C11 114.55(13) . . ?
C2 C10 C11 123.35(14) . . ?
C12 C11 C16 119.46(15) . . ?
C12 C11 C10 119.55(14) . . ?
C16 C11 C10 120.95(14) . . ?
C13 C12 C11 119.84(15) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 120.23(15) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C13 C14 C15 120.95(15) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 118.38(15) . . ?
C16 C15 C17 120.49(15) . . ?
C14 C15 C17 121.09(15) . . ?
C15 C16 C11 121.11(15) . . ?
C15 C16 H16A 119.4 . . ?
C11 C16 H16A 119.4 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
N1 C1 C2 C10 -167.8(17) . . . . ?
N1 C1 C2 C3 6.5(18) . . . . ?
C10 C2 C3 C4 92.97(18) . . . . ?
C1 C2 C3 C4 -81.06(17) . . . . ?
C2 C3 C4 C9 141.11(15) . . . . ?
C2 C3 C4 C5 -39.2(2) . . . . ?
C9 C4 C5 C6 1.8(2) . . . . ?
C3 C4 C5 C6 -177.95(14) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C6 C7 C8 C9 1.7(2) . . . . ?
C7 C8 C9 C4 -0.9(2) . . . . ?
C5 C4 C9 C8 -0.9(2) . . . . ?
C3 C4 C9 C8 178.86(14) . . . . ?
C1 C2 C10 N2 172.34(15) . . . . ?
C3 C2 C10 N2 -1.4(2) . . . . ?
C1 C2 C10 C11 -5.3(2) . . . . ?
C3 C2 C10 C11 -179.10(14) . . . . ?
N2 C10 C11 C12 -49.8(2) . . . . ?
C2 C10 C11 C12 128.02(17) . . . . ?
N2 C10 C11 C16 127.96(16) . . . . ?
C2 C10 C11 C16 -54.2(2) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
C10 C11 C12 C13 178.46(14) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C13 C14 C15 C17 -177.13(14) . . . . ?
C14 C15 C16 C11 -1.4(2) . . . . ?
C17 C15 C16 C11 176.73(14) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
C10 C11 C16 C15 -177.19(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_Compound4ag
_database_code_depnum_ccdc_archive 'CCDC 1936386'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca21
_symmetry_space_group_name_Hall  'P 2c -2ac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   12.9687(3)
_cell_length_b                   13.0705(3)
_cell_length_c                   7.1800(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1217.05(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4469
_cell_measurement_theta_min      4.7770
_cell_measurement_theta_max      73.1210

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9132
_exptl_absorpt_correction_T_max  0.9639
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6331
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         69.96
_reflns_number_total             2150
_reflns_number_gt                2108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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. 
;

# start Validation Reply Form
_vrf_STRVA01_Compound4ag         
;
PROBLEM:  Flack parameter is too small 
RESPONSE: The flack parameter could be decreased down to 0.00(4) when the 
commands of TWIN and BASF were used in the refinement of this structure, and 
no ALERT C would be given about this problem. However, the other problem arose
when the TWIN/BASF were used for refinement, i.e. the absolute value of 
parameter shift to su ratio would be given as 0.75 in the refinement, and 
additional refinement cycles could NOT make it better. That would be a ALERT A 
in the checkCIF system. Therefore, the structure was finally refined without 
the TWIN/BASF refinement. 
;
# end Validation Reply Form



_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)+(0.0482P)²+0.1608P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
N1 N 0.59397(9) 0.79037(9) 1.00983(17) 0.0243(3) Uani 1 1 d . . .
N2 N 0.46298(9) 0.78381(9) 0.38812(17) 0.0240(3) Uani 1 1 d . . .
H2A H 0.5060 0.7481 0.3190 0.029 Uiso 1 1 calc R . .
H2B H 0.4055 0.8075 0.3395 0.029 Uiso 1 1 calc R . .
N3 N 0.22855(8) 0.88194(8) 0.76091(17) 0.0207(2) Uani 1 1 d . . .
C1 C 0.58279(9) 0.78238(9) 0.8510(2) 0.0189(3) Uani 1 1 d . . .
C2 C 0.57259(10) 0.76832(10) 0.65514(19) 0.0182(3) Uani 1 1 d . . .
C3 C 0.65658(10) 0.70983(9) 0.5546(2) 0.0201(3) Uani 1 1 d . . .
H3B H 0.7226 0.7224 0.6198 0.024 Uiso 1 1 calc R . .
H3A H 0.6632 0.7384 0.4274 0.024 Uiso 1 1 calc R . .
C4 C 0.64143(10) 0.59452(10) 0.53821(18) 0.0187(3) Uani 1 1 d . . .
C5 C 0.72133(10) 0.53585(11) 0.46480(19) 0.0222(3) Uani 1 1 d . . .
H5A H 0.7834 0.5682 0.4265 0.027 Uiso 1 1 calc R . .
C6 C 0.71133(11) 0.43057(11) 0.4469(2) 0.0259(3) Uani 1 1 d . . .
H6A H 0.7663 0.3914 0.3963 0.031 Uiso 1 1 calc R . .
C7 C 0.62125(11) 0.38243(10) 0.5028(2) 0.0247(3) Uani 1 1 d . . .
H7A H 0.6144 0.3103 0.4913 0.030 Uiso 1 1 calc R . .
C8 C 0.54128(11) 0.44027(10) 0.5754(2) 0.0241(3) Uani 1 1 d . . .
H8A H 0.4793 0.4076 0.6137 0.029 Uiso 1 1 calc R . .
C9 C 0.55107(10) 0.54588(10) 0.5928(2) 0.0212(3) Uani 1 1 d . . .
H9A H 0.4957 0.5849 0.6422 0.025 Uiso 1 1 calc R . .
C10 C 0.48522(10) 0.80214(9) 0.5684(2) 0.0183(3) Uani 1 1 d . . .
C11 C 0.40594(10) 0.86420(9) 0.66720(19) 0.0171(3) Uani 1 1 d . . .
C12 C 0.42749(10) 0.96156(10) 0.7348(2) 0.0212(3) Uani 1 1 d . . .
H12A H 0.4952 0.9889 0.7266 0.025 Uiso 1 1 calc R . .
C13 C 0.34857(10) 1.01808(10) 0.8143(2) 0.0230(3) Uani 1 1 d . . .
H13A H 0.3613 1.0848 0.8615 0.028 Uiso 1 1 calc R . .
C14 C 0.25099(11) 0.97593(9) 0.8239(2) 0.0222(3) Uani 1 1 d . . .
H14A H 0.1972 1.0155 0.8777 0.027 Uiso 1 1 calc R . .
C15 C 0.30545(10) 0.82798(9) 0.68471(18) 0.0178(3) Uani 1 1 d . . .
H15A H 0.2906 0.7612 0.6400 0.021 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
N1 C1 1.1542(19) . ?
N2 C10 1.3477(18) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C15 1.3384(17) . ?
N3 C14 1.3411(17) . ?
C1 C2 1.4244(19) . ?
C2 C10 1.3664(19) . ?
C2 C3 1.5141(17) . ?
C3 C4 1.5244(17) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C9 1.3897(19) . ?
C4 C5 1.3926(18) . ?
C5 C6 1.3881(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.385(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3917(19) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.4893(18) . ?
C11 C12 1.3903(18) . ?
C11 C15 1.3922(17) . ?
C12 C13 1.3854(19) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?

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
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C15 N3 C14 117.31(11) . . ?
N1 C1 C2 177.10(14) . . ?
C10 C2 C1 119.02(12) . . ?
C10 C2 C3 122.86(12) . . ?
C1 C2 C3 117.98(12) . . ?
C2 C3 C4 116.31(11) . . ?
C2 C3 H3B 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3A 108.2 . . ?
H3B C3 H3A 107.4 . . ?
C9 C4 C5 118.83(12) . . ?
C9 C4 C3 122.63(11) . . ?
C5 C4 C3 118.54(12) . . ?
C6 C5 C4 120.75(13) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C7 C6 C5 120.13(12) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C8 C7 C6 119.48(12) . . ?
C8 C7 H7A 120.3 . . ?
C6 C7 H7A 120.3 . . ?
C7 C8 C9 120.44(13) . . ?
C7 C8 H8A 119.8 . . ?
C9 C8 H8A 119.8 . . ?
C4 C9 C8 120.36(13) . . ?
C4 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
N2 C10 C2 123.89(12) . . ?
N2 C10 C11 113.99(12) . . ?
C2 C10 C11 122.12(12) . . ?
C12 C11 C15 117.90(12) . . ?
C12 C11 C10 121.73(12) . . ?
C15 C11 C10 120.27(11) . . ?
C13 C12 C11 118.91(12) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C14 C13 C12 118.98(12) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
N3 C14 C13 123.17(12) . . ?
N3 C14 H14A 118.4 . . ?
C13 C14 H14A 118.4 . . ?
N3 C15 C11 123.73(12) . . ?
N3 C15 H15A 118.1 . . ?
C11 C15 H15A 118.1 . . ?

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 C1 C2 C10 157(3) . . . . ?
N1 C1 C2 C3 -19(3) . . . . ?
C10 C2 C3 C4 -85.23(16) . . . . ?
C1 C2 C3 C4 90.54(15) . . . . ?
C2 C3 C4 C9 7.03(19) . . . . ?
C2 C3 C4 C5 -173.26(12) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C6 -179.97(13) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C3 C4 C9 C8 -179.81(13) . . . . ?
C7 C8 C9 C4 -0.3(2) . . . . ?
C1 C2 C10 N2 -173.09(12) . . . . ?
C3 C2 C10 N2 2.6(2) . . . . ?
C1 C2 C10 C11 7.49(18) . . . . ?
C3 C2 C10 C11 -176.78(11) . . . . ?
N2 C10 C11 C12 -114.90(14) . . . . ?
C2 C10 C11 C12 64.57(17) . . . . ?
N2 C10 C11 C15 61.30(16) . . . . ?
C2 C10 C11 C15 -119.23(14) . . . . ?
C15 C11 C12 C13 -0.6(2) . . . . ?
C10 C11 C12 C13 175.72(13) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C15 N3 C14 C13 -0.4(2) . . . . ?
C12 C13 C14 N3 0.5(2) . . . . ?
C14 N3 C15 C11 -0.2(2) . . . . ?
C12 C11 C15 N3 0.7(2) . . . . ?
C10 C11 C15 N3 -175.61(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        69.96
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_Compound3h
_database_code_depnum_ccdc_archive 'CCDC 1914064'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N3'
_chemical_formula_sum            'C22 H17 N3'
_chemical_formula_weight         323.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8058(8)
_cell_length_b                   10.1568(9)
_cell_length_c                   10.8636(10)
_cell_angle_alpha                112.118(9)
_cell_angle_beta                 90.659(8)
_cell_angle_gamma                106.960(8)
_cell_volume                     852.86(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1761
_cell_measurement_theta_min      4.4110
_cell_measurement_theta_max      72.7420

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5031
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.44
_diffrn_reflns_theta_max         69.48
_reflns_number_total             3154
_reflns_number_gt                2312
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)+(0.0304P)²+0.6206P] 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         3154
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_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
N1 N -0.0151(4) 0.9684(3) 0.1579(3) 0.0577(7) Uani 1 1 d . . .
H1A H -0.0238 1.0329 0.1244 0.069 Uiso 1 1 calc R . .
H1B H -0.0665 0.9610 0.2252 0.069 Uiso 1 1 calc R . .
N2 N 0.2663(3) 0.7094(3) -0.0091(2) 0.0382(5) Uani 1 1 d . . .
N3 N 0.1514(3) 0.8986(3) 0.0035(2) 0.0414(5) Uani 1 1 d . . .
C1 C 0.0765(3) 0.8813(3) 0.1062(3) 0.0403(6) Uani 1 1 d . . .
C2 C 0.0959(3) 0.7778(3) 0.1586(2) 0.0363(6) Uani 1 1 d . . .
C3 C 0.0151(3) 0.7703(3) 0.2767(3) 0.0392(6) Uani 1 1 d . . .
C4 C 0.1053(4) 0.8151(3) 0.4000(3) 0.0481(7) Uani 1 1 d . . .
H4A H 0.2190 0.8497 0.4086 0.058 Uiso 1 1 calc R . .
C5 C 0.0308(4) 0.8094(4) 0.5093(3) 0.0600(9) Uani 1 1 d . . .
H5A H 0.0934 0.8374 0.5923 0.072 Uiso 1 1 calc R . .
C6 C -0.1343(5) 0.7635(4) 0.4994(3) 0.0652(9) Uani 1 1 d . . .
H6A H -0.1850 0.7622 0.5758 0.078 Uiso 1 1 calc R . .
C7 C -0.2252(4) 0.7194(4) 0.3781(3) 0.0569(8) Uani 1 1 d . . .
H7A H -0.3388 0.6877 0.3710 0.068 Uiso 1 1 calc R . .
C8 C -0.1516(4) 0.7212(3) 0.2668(3) 0.0482(7) Uani 1 1 d . . .
H8A H -0.2149 0.6888 0.1831 0.058 Uiso 1 1 calc R . .
C9 C 0.1913(3) 0.6929(3) 0.0961(2) 0.0367(6) Uani 1 1 d . . .
C10 C 0.2235(3) 0.5772(3) 0.1361(3) 0.0390(6) Uani 1 1 d . . .
C11 C 0.1088(3) 0.4875(3) 0.1835(3) 0.0434(6) Uani 1 1 d . . .
H11A H 0.0068 0.5015 0.1938 0.052 Uiso 1 1 calc R . .
C12 C 0.1422(4) 0.3783(3) 0.2156(3) 0.0518(7) Uani 1 1 d . . .
H12A H 0.0634 0.3188 0.2489 0.062 Uiso 1 1 calc R . .
C13 C 0.2886(4) 0.3550(4) 0.1996(3) 0.0575(8) Uani 1 1 d . . .
H13A H 0.3104 0.2791 0.2208 0.069 Uiso 1 1 calc R . .
C14 C 0.4037(4) 0.4432(4) 0.1525(3) 0.0576(8) Uani 1 1 d . . .
H14A H 0.5051 0.4281 0.1416 0.069 Uiso 1 1 calc R . .
C15 C 0.3712(4) 0.5534(4) 0.1214(3) 0.0494(7) Uani 1 1 d . . .
H15A H 0.4509 0.6136 0.0894 0.059 Uiso 1 1 calc R . .
C16 C 0.2422(3) 0.8118(3) -0.0482(3) 0.0369(6) Uani 1 1 d . . .
C17 C 0.3200(3) 0.8299(3) -0.1646(3) 0.0411(6) Uani 1 1 d . . .
C18 C 0.3272(4) 0.7058(4) -0.2733(3) 0.0508(7) Uani 1 1 d . . .
H18A H 0.2834 0.6085 -0.2734 0.061 Uiso 1 1 calc R . .
C19 C 0.3981(4) 0.7229(4) -0.3823(3) 0.0638(9) Uani 1 1 d . . .
H19A H 0.4009 0.6372 -0.4574 0.077 Uiso 1 1 calc R . .
C20 C 0.4641(4) 0.8639(5) -0.3817(4) 0.0648(10) Uani 1 1 d . . .
H20A H 0.5148 0.8755 -0.4553 0.078 Uiso 1 1 calc R . .
C21 C 0.4569(4) 0.9881(4) -0.2745(4) 0.0619(9) Uani 1 1 d . . .
H21A H 0.5013 1.0851 -0.2750 0.074 Uiso 1 1 calc R . .
C22 C 0.3850(4) 0.9721(4) -0.1660(3) 0.0501(7) Uani 1 1 d . . .
H22A H 0.3799 1.0581 -0.0923 0.060 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
N1 C1 1.342(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C16 1.329(3) . ?
N2 C9 1.366(3) . ?
N3 C16 1.335(3) . ?
N3 C1 1.345(3) . ?
C1 C2 1.418(3) . ?
C2 C9 1.380(4) . ?
C2 C3 1.491(3) . ?
C3 C4 1.391(4) . ?
C3 C8 1.394(4) . ?
C4 C5 1.376(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.378(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.382(4) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C10 1.492(3) . ?
C10 C15 1.391(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.385(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.379(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.491(3) . ?
C17 C18 1.383(4) . ?
C17 C22 1.396(4) . ?
C18 C19 1.390(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.377(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.376(5) . ?
C20 H20A 0.9500 . ?
C21 C22 1.385(4) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?

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
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C16 N2 C9 116.3(2) . . ?
C16 N3 C1 116.8(2) . . ?
N1 C1 N3 116.7(2) . . ?
N1 C1 C2 121.8(2) . . ?
N3 C1 C2 121.5(2) . . ?
C9 C2 C1 116.6(2) . . ?
C9 C2 C3 125.2(2) . . ?
C1 C2 C3 118.3(2) . . ?
C4 C3 C8 118.8(3) . . ?
C4 C3 C2 120.3(3) . . ?
C8 C3 C2 120.9(2) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C7 C8 C3 120.3(3) . . ?
C7 C8 H8A 119.8 . . ?
C3 C8 H8A 119.8 . . ?
N2 C9 C2 122.0(2) . . ?
N2 C9 C10 113.9(2) . . ?
C2 C9 C10 124.0(2) . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C9 119.1(2) . . ?
C11 C10 C9 122.5(2) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15A 119.5 . . ?
C10 C15 H15A 119.5 . . ?
N2 C16 N3 126.9(2) . . ?
N2 C16 C17 117.4(2) . . ?
N3 C16 C17 115.7(2) . . ?
C18 C17 C22 119.1(3) . . ?
C18 C17 C16 120.5(2) . . ?
C22 C17 C16 120.4(3) . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C21 C22 C17 120.1(3) . . ?
C21 C22 H22A 119.9 . . ?
C17 C22 H22A 119.9 . . ?

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
C16 N3 C1 N1 -179.8(3) . . . . ?
C16 N3 C1 C2 1.3(4) . . . . ?
N1 C1 C2 C9 179.2(3) . . . . ?
N3 C1 C2 C9 -2.0(4) . . . . ?
N1 C1 C2 C3 -1.7(4) . . . . ?
N3 C1 C2 C3 177.1(3) . . . . ?
C9 C2 C3 C4 65.7(4) . . . . ?
C1 C2 C3 C4 -113.3(3) . . . . ?
C9 C2 C3 C8 -115.5(3) . . . . ?
C1 C2 C3 C8 65.5(4) . . . . ?
C8 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 C5 179.4(3) . . . . ?
C3 C4 C5 C6 -1.9(5) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C6 C7 C8 C3 -1.2(5) . . . . ?
C4 C3 C8 C7 0.9(4) . . . . ?
C2 C3 C8 C7 -177.9(3) . . . . ?
C16 N2 C9 C2 -0.1(4) . . . . ?
C16 N2 C9 C10 -179.6(2) . . . . ?
C1 C2 C9 N2 1.4(4) . . . . ?
C3 C2 C9 N2 -177.6(3) . . . . ?
C1 C2 C9 C10 -179.1(3) . . . . ?
C3 C2 C9 C10 1.8(4) . . . . ?
N2 C9 C10 C15 32.1(4) . . . . ?
C2 C9 C10 C15 -147.4(3) . . . . ?
N2 C9 C10 C11 -145.5(3) . . . . ?
C2 C9 C10 C11 35.0(4) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
C9 C10 C11 C12 178.0(3) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C10 -0.2(5) . . . . ?
C11 C10 C15 C14 0.1(5) . . . . ?
C9 C10 C15 C14 -177.5(3) . . . . ?
C9 N2 C16 N3 -0.7(4) . . . . ?
C9 N2 C16 C17 -178.7(2) . . . . ?
C1 N3 C16 N2 0.2(4) . . . . ?
C1 N3 C16 C17 178.2(3) . . . . ?
N2 C16 C17 C18 39.3(4) . . . . ?
N3 C16 C17 C18 -139.0(3) . . . . ?
N2 C16 C17 C22 -141.4(3) . . . . ?
N3 C16 C17 C22 40.4(4) . . . . ?
C22 C17 C18 C19 -0.1(5) . . . . ?
C16 C17 C18 C19 179.3(3) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C18 C19 C20 C21 -1.5(5) . . . . ?
C19 C20 C21 C22 0.9(5) . . . . ?
C20 C21 C22 C17 0.2(5) . . . . ?
C18 C17 C22 C21 -0.6(5) . . . . ?
C16 C17 C22 C21 -179.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        69.48
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
