# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_xb2179_0m
_database_code_depnum_ccdc_archive 'CCDC 1965066'
loop_
_audit_author_name
_audit_author_address
'TY Yu'
;Northwest University
China
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3'
_chemical_formula_weight         299.36

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7352(18)
_cell_length_b                   10.022(2)
_cell_length_c                   10.902(3)
_cell_angle_alpha                75.534(4)
_cell_angle_beta                 83.910(4)
_cell_angle_gamma                71.785(3)
_cell_volume                     777.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2006
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   0.6663
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean none
_diffrn_reflns_number            4220
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.198
_diffrn_reflns_theta_max         26.089
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3017
_reflns_number_gt                2417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.087(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3017
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_restrained_S_all      0.867
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.18135(17) 0.24018(13) 0.71185(11) 0.0442(3) Uani 1 1 d . . . . .
N3 N -0.10011(18) 0.39638(15) 0.63931(12) 0.0514(4) Uani 1 1 d . . . . .
C3 C 0.4570(2) 0.15839(15) 0.80140(15) 0.0466(4) Uani 1 1 d . . . . .
N2 N 0.0845(2) 0.23208(17) 0.52009(13) 0.0600(4) Uani 1 1 d . . . . .
C5 C 0.1550(2) 0.24795(15) 0.84040(14) 0.0434(4) Uani 1 1 d . . . . .
C6 C 0.3198(2) 0.19829(17) 0.89458(15) 0.0485(4) Uani 1 1 d . . . . .
H6 H 0.3399 0.1914 0.9788 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0474(2) 0.29227(16) 0.61930(14) 0.0451(4) Uani 1 1 d . . . . .
C8 C 0.3691(2) 0.18361(15) 0.68796(14) 0.0447(4) Uani 1 1 d . . . . .
C9 C -0.2096(2) 0.28478(18) 1.10876(13) 0.0500(4) Uani 1 1 d . . . . .
C10 C -0.4782(2) 0.45889(19) 1.16843(16) 0.0576(4) Uani 1 1 d . . . . .
H10 H -0.5394 0.5538 1.1723 0.069 Uiso 1 1 calc R U . . .
C11 C -0.0286(2) 0.29370(18) 0.90310(14) 0.0493(4) Uani 1 1 d . . . . .
H11A H -0.1093 0.2509 0.8751 0.059 Uiso 1 1 calc R U . . .
H11B H -0.0786 0.3977 0.8769 0.059 Uiso 1 1 calc R U . . .
C12 C -0.2958(3) 0.17959(19) 1.15649(17) 0.0621(5) Uani 1 1 d . . . . .
H12 H -0.2351 0.0844 1.1534 0.074 Uiso 1 1 calc R U . . .
C13 C -0.5622(2) 0.3531(2) 1.21445(16) 0.0588(5) Uani 1 1 d . . . . .
H13 H -0.6800 0.3760 1.2491 0.071 Uiso 1 1 calc R U . . .
C14 C -0.3043(2) 0.42509(18) 1.11667(15) 0.0536(4) Uani 1 1 d . . . . .
H14 H -0.2491 0.4977 1.0864 0.064 Uiso 1 1 calc R U . . .
C15 C 0.6458(2) 0.10207(18) 0.80558(18) 0.0558(4) Uani 1 1 d . . . . .
H15 H 0.7052 0.0857 0.8802 0.067 Uiso 1 1 calc R U . . .
C16 C -0.2219(2) 0.4442(2) 0.54861(17) 0.0613(5) Uani 1 1 d . . . . .
H16 H -0.3294 0.5154 0.5594 0.074 Uiso 1 1 calc R U . . .
C17 C -0.1969(3) 0.3939(2) 0.44056(17) 0.0672(5) Uani 1 1 d . . . . .
H17 H -0.2826 0.4305 0.3775 0.081 Uiso 1 1 calc R U . . .
C18 C 0.4679(2) 0.15262(18) 0.57839(16) 0.0549(4) Uani 1 1 d . . . . .
H18 H 0.4101 0.1692 0.5031 0.066 Uiso 1 1 calc R U . . .
C19 C 0.7433(2) 0.07103(19) 0.6978(2) 0.0624(5) Uani 1 1 d . . . . .
H19 H 0.8694 0.0328 0.6998 0.075 Uiso 1 1 calc R U . . .
C20 C -0.0223(2) 0.2498(2) 1.04741(15) 0.0625(5) Uani 1 1 d . . . . .
H20A H 0.0373 0.1469 1.0735 0.075 Uiso 1 1 calc R U . . .
H20B H 0.0492 0.2995 1.0762 0.075 Uiso 1 1 calc R U . . .
C21 C -0.4701(3) 0.2135(2) 1.20858(18) 0.0652(5) Uani 1 1 d . . . . .
H21 H -0.5255 0.1412 1.2399 0.078 Uiso 1 1 calc R U . . .
C22 C 0.6550(2) 0.09627(19) 0.58634(19) 0.0624(5) Uani 1 1 d . . . . .
H22 H 0.7238 0.0746 0.5147 0.075 Uiso 1 1 calc R U . . .
C23 C -0.0394(3) 0.2871(2) 0.43050(18) 0.0688(5) Uani 1 1 d . . . . .
H23 H -0.0173 0.2510 0.3578 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.4063(19) . ?
N1 C7 1.409(2) . ?
N1 C5 1.4127(19) . ?
N3 C7 1.325(2) . ?
N3 C16 1.332(2) . ?
C3 C15 1.393(2) . ?
C3 C8 1.404(2) . ?
C3 C6 1.424(2) . ?
N2 C7 1.330(2) . ?
N2 C23 1.333(2) . ?
C5 C6 1.356(2) . ?
C5 C11 1.496(2) . ?
C6 H6 0.9300 . ?
C8 C18 1.397(2) . ?
C9 C12 1.385(3) . ?
C9 C14 1.387(2) . ?
C9 C20 1.504(2) . ?
C10 C14 1.376(2) . ?
C10 C13 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C20 1.526(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C21 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C21 1.371(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C19 1.376(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 C23 1.363(3) . ?
C17 H17 0.9300 . ?
C18 C22 1.383(2) . ?
C18 H18 0.9300 . ?
C19 C22 1.387(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 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
C8 N1 C7 124.98(13) . . ?
C8 N1 C5 108.05(12) . . ?
C7 N1 C5 126.71(13) . . ?
C7 N3 C16 115.04(15) . . ?
C15 C3 C8 119.88(16) . . ?
C15 C3 C6 132.75(16) . . ?
C8 C3 C6 107.36(14) . . ?
C7 N2 C23 115.28(16) . . ?
C6 C5 N1 108.45(13) . . ?
C6 C5 C11 127.86(14) . . ?
N1 C5 C11 123.54(13) . . ?
C5 C6 C3 108.85(15) . . ?
C5 C6 H6 125.6 . . ?
C3 C6 H6 125.6 . . ?
N3 C7 N2 127.07(15) . . ?
N3 C7 N1 116.96(13) . . ?
N2 C7 N1 115.96(14) . . ?
C18 C8 C3 121.09(15) . . ?
C18 C8 N1 131.63(15) . . ?
C3 C8 N1 107.28(13) . . ?
C12 C9 C14 117.51(16) . . ?
C12 C9 C20 121.56(16) . . ?
C14 C9 C20 120.91(17) . . ?
C14 C10 C13 120.39(16) . . ?
C14 C10 H10 119.8 . . ?
C13 C10 H10 119.8 . . ?
C5 C11 C20 112.65(13) . . ?
C5 C11 H11A 109.1 . . ?
C20 C11 H11A 109.1 . . ?
C5 C11 H11B 109.1 . . ?
C20 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C21 C12 C9 121.18(16) . . ?
C21 C12 H12 119.4 . . ?
C9 C12 H12 119.4 . . ?
C21 C13 C10 119.18(17) . . ?
C21 C13 H13 120.4 . . ?
C10 C13 H13 120.4 . . ?
C10 C14 C9 121.27(16) . . ?
C10 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C19 C15 C3 119.11(17) . . ?
C19 C15 H15 120.4 . . ?
C3 C15 H15 120.4 . . ?
N3 C16 C17 123.35(17) . . ?
N3 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
C23 C17 C16 116.16(16) . . ?
C23 C17 H17 121.9 . . ?
C16 C17 H17 121.9 . . ?
C22 C18 C8 117.36(17) . . ?
C22 C18 H18 121.3 . . ?
C8 C18 H18 121.3 . . ?
C15 C19 C22 120.49(16) . . ?
C15 C19 H19 119.8 . . ?
C22 C19 H19 119.8 . . ?
C9 C20 C11 111.96(13) . . ?
C9 C20 H20A 109.2 . . ?
C11 C20 H20A 109.2 . . ?
C9 C20 H20B 109.2 . . ?
C11 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C13 C21 C12 120.46(18) . . ?
C13 C21 H21 119.8 . . ?
C12 C21 H21 119.8 . . ?
C18 C22 C19 122.06(17) . . ?
C18 C22 H22 119.0 . . ?
C19 C22 H22 119.0 . . ?
N2 C23 C17 123.02(18) . . ?
N2 C23 H23 118.5 . . ?
C17 C23 H23 118.5 . . ?

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
C8 N1 C5 C6 0.04(17) . . . . ?
C7 N1 C5 C6 -174.27(13) . . . . ?
C8 N1 C5 C11 -175.78(14) . . . . ?
C7 N1 C5 C11 9.9(2) . . . . ?
N1 C5 C6 C3 0.52(17) . . . . ?
C11 C5 C6 C3 176.10(15) . . . . ?
C15 C3 C6 C5 -179.98(16) . . . . ?
C8 C3 C6 C5 -0.88(18) . . . . ?
C16 N3 C7 N2 -0.2(3) . . . . ?
C16 N3 C7 N1 178.92(14) . . . . ?
C23 N2 C7 N3 2.2(3) . . . . ?
C23 N2 C7 N1 -176.93(15) . . . . ?
C8 N1 C7 N3 -150.07(14) . . . . ?
C5 N1 C7 N3 23.3(2) . . . . ?
C8 N1 C7 N2 29.1(2) . . . . ?
C5 N1 C7 N2 -157.46(15) . . . . ?
C15 C3 C8 C18 0.2(2) . . . . ?
C6 C3 C8 C18 -178.99(14) . . . . ?
C15 C3 C8 N1 -179.88(13) . . . . ?
C6 C3 C8 N1 0.89(16) . . . . ?
C7 N1 C8 C18 -6.3(3) . . . . ?
C5 N1 C8 C18 179.27(16) . . . . ?
C7 N1 C8 C3 173.85(13) . . . . ?
C5 N1 C8 C3 -0.59(16) . . . . ?
C6 C5 C11 C20 -12.5(2) . . . . ?
N1 C5 C11 C20 162.45(15) . . . . ?
C14 C9 C12 C21 0.8(3) . . . . ?
C20 C9 C12 C21 -177.69(16) . . . . ?
C14 C10 C13 C21 0.3(3) . . . . ?
C13 C10 C14 C9 0.4(3) . . . . ?
C12 C9 C14 C10 -0.9(2) . . . . ?
C20 C9 C14 C10 177.58(15) . . . . ?
C8 C3 C15 C19 -0.4(2) . . . . ?
C6 C3 C15 C19 178.56(17) . . . . ?
C7 N3 C16 C17 -1.8(3) . . . . ?
N3 C16 C17 C23 1.6(3) . . . . ?
C3 C8 C18 C22 0.0(2) . . . . ?
N1 C8 C18 C22 -179.83(15) . . . . ?
C3 C15 C19 C22 0.4(3) . . . . ?
C12 C9 C20 C11 101.50(19) . . . . ?
C14 C9 C20 C11 -76.9(2) . . . . ?
C5 C11 C20 C9 -174.93(14) . . . . ?
C10 C13 C21 C12 -0.4(3) . . . . ?
C9 C12 C21 C13 -0.1(3) . . . . ?
C8 C18 C22 C19 -0.1(3) . . . . ?
C15 C19 C22 C18 -0.1(3) . . . . ?
C7 N2 C23 C17 -2.4(3) . . . . ?
C16 C17 C23 N2 0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18 N2 0.93 2.40 2.916(2) 115.2 .
C18 H18 N2 0.93 2.40 2.916(2) 115.2 .
C18 H18 N2 0.93 2.40 2.916(2) 115.2 .
C18 H18 N2 0.93 2.40 2.916(2) 115.2 .
C18 H18 N2 0.93 2.40 2.916(2) 115.2 .

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034

