# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_C008_0m
_database_code_depnum_ccdc_archive 'CCDC 2374105'
loop_
_audit_author_name
_audit_author_address
'Qinghe Gao'
;Xinxiang Medical University
China
;
_audit_update_record             
;
2024-07-29 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N3'
_chemical_formula_sum            'C23 H17 N3'
_chemical_formula_weight         335.39
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.185(8)
_cell_length_b                   10.136(8)
_cell_length_c                   10.439(9)
_cell_angle_alpha                80.364(9)
_cell_angle_beta                 67.002(9)
_cell_angle_gamma                73.546(10)
_cell_volume                     856.2(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    687
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.87
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5080
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.645
_diffrn_reflns_theta_min         2.099
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1996
_reflns_number_total             3817
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.079) H7(0.082) H6(0.074) H5(0.064) H4(0.063) H2(0.072)
 H3(0.072) H9(0.075) H8(0.065) H16(0.057) H12(0.066) H10(0.068) H11(0.061)
 H15(0.115) H13(0.115) H14(0.115) H17(0.063)
 Fixed X: H1(0.563748) H7(0.303077) H6(0.174193) H5(0.249966) H4(-0.021573)
 H2(-0.132227) H3(-0.131254) H9(0.695781) H8(0.565967) H16(0.410771)
 H12(0.36547) H10(0.198975) H11(0.143846) H15(0.465786) H13(0.537467)
 H14(0.618108) H17(-0.026092)
 Fixed Y: H1(-0.030459) H7(-0.011474) H6(0.177481) H5(0.282512) H4(0.697284)
 H2(0.926598) H3(1.088511) H9(0.14053) H8(0.332872) H16(0.698339) H12(0.650858)
 H10(0.505251) H11(0.448525) H15(0.87418) H13(0.786532) H14(0.7498)
 H17(1.028324)
 Fixed Z: H1(0.252934) H7(0.412556) H6(0.543511) H5(0.727918) H4(1.001116)
 H2(1.039096) H3(0.854207) H9(0.222465) H8(0.35008) H16(0.318674) H12(-
 0.033845) H10(0.083939) H11(0.318378) H15(0.084948) H13(-0.04578)
 H14(0.067202) H17(0.629124)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.1579(3) 0.4689(2) 0.7817(2) 0.0521(6) Uani 1 1 d . . . . .
N2 N 0.1637(3) 0.6294(2) 0.5852(2) 0.0422(5) Uani 1 1 d . . . . .
N3 N 0.1163(3) 0.7655(2) 0.5514(2) 0.0486(6) Uani 1 1 d . . . . .
C1 C 0.5115(4) 0.0467(3) 0.3052(3) 0.0662(9) Uani 1 1 d . . . . .
H1 H 0.563748 -0.030459 0.252934 0.079 Uiso 1 1 calc R U . . .
C2 C 0.3562(4) 0.0579(3) 0.4004(4) 0.0686(9) Uani 1 1 d . . . . .
H7 H 0.303077 -0.011474 0.412556 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2791(4) 0.1711(3) 0.4779(3) 0.0619(8) Uani 1 1 d . . . . .
H6 H 0.174193 0.177481 0.543511 0.074 Uiso 1 1 calc R U . . .
C4 C 0.3554(3) 0.2759(3) 0.4597(3) 0.0467(6) Uani 1 1 d . . . . .
C5 C 0.2719(3) 0.3955(3) 0.5464(3) 0.0441(6) Uani 1 1 d . . . . .
C6 C 0.2276(3) 0.3733(3) 0.6923(3) 0.0533(7) Uani 1 1 d . . . . .
H5 H 0.249966 0.282512 0.727918 0.064 Uiso 1 1 calc R U . . .
C7 C 0.1244(3) 0.5980(2) 0.7278(2) 0.0423(6) Uani 1 1 d . . . . .
C8 C 0.0468(3) 0.7235(3) 0.7893(3) 0.0439(6) Uani 1 1 d . . . . .
C9 C -0.0213(3) 0.7625(3) 0.9269(3) 0.0524(7) Uani 1 1 d . . . . .
H4 H -0.021573 0.697284 1.001116 0.063 Uiso 1 1 calc R U . . .
C10 C -0.0866(4) 0.8979(3) 0.9487(3) 0.0599(8) Uani 1 1 d . . . . .
H2 H -0.132227 0.926598 1.039096 0.072 Uiso 1 1 calc R U . . .
C11 C -0.0863(4) 0.9961(3) 0.8358(3) 0.0601(8) Uani 1 1 d . . . . .
H3 H -0.131254 1.088511 0.854207 0.072 Uiso 1 1 calc R U . . .
C12 C 0.5900(4) 0.1487(3) 0.2868(3) 0.0623(8) Uani 1 1 d . . . . .
H9 H 0.695781 0.140530 0.222465 0.075 Uiso 1 1 calc R U . . .
C13 C 0.5126(4) 0.2635(3) 0.3632(3) 0.0538(7) Uani 1 1 d . . . . .
H8 H 0.565967 0.332872 0.350080 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2380(3) 0.5287(2) 0.4922(2) 0.0423(6) Uani 1 1 d . . . . .
C15 C 0.2716(3) 0.5681(2) 0.3422(2) 0.0424(6) Uani 1 1 d . . . . .
C16 C 0.3696(3) 0.6581(3) 0.2706(3) 0.0473(7) Uani 1 1 d . . . . .
H16 H 0.410771 0.698339 0.318674 0.057 Uiso 1 1 calc R U . . .
C17 C 0.4075(3) 0.6893(3) 0.1294(3) 0.0494(7) Uani 1 1 d . . . . .
C18 C 0.3421(4) 0.6305(3) 0.0613(3) 0.0550(7) Uani 1 1 d . . . . .
H12 H 0.365470 0.650858 -0.033845 0.066 Uiso 1 1 calc R U . . .
C19 C 0.2433(4) 0.5428(3) 0.1314(3) 0.0564(8) Uani 1 1 d . . . . .
H10 H 0.198975 0.505251 0.083939 0.068 Uiso 1 1 calc R U . . .
C20 C 0.2090(3) 0.5099(3) 0.2715(3) 0.0507(7) Uani 1 1 d . . . . .
H11 H 0.143846 0.448525 0.318378 0.061 Uiso 1 1 calc R U . . .
C21 C 0.5170(5) 0.7833(4) 0.0521(3) 0.0769(10) Uani 1 1 d . . . . .
H15 H 0.465786 0.874180 0.084948 0.115 Uiso 1 1 calc R U . . .
H13 H 0.537467 0.786532 -0.045780 0.115 Uiso 1 1 calc R U . . .
H14 H 0.618108 0.749800 0.067202 0.115 Uiso 1 1 calc R U . . .
C22 C 0.0458(3) 0.8212(3) 0.6769(3) 0.0451(6) Uani 1 1 d . . . . .
C23 C -0.0236(3) 0.9618(3) 0.7018(3) 0.0525(7) Uani 1 1 d . . . . .
H17 H -0.026092 1.028324 0.629124 0.063 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 C6 1.306(3) . ?
N1 C7 1.336(3) . ?
N2 N3 1.354(3) . ?
N2 C7 1.391(3) . ?
N2 C14 1.367(3) . ?
N3 C22 1.354(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(5) . ?
C1 C12 1.370(4) . ?
C2 H7 0.9300 . ?
C2 C3 1.370(4) . ?
C3 H6 0.9300 . ?
C3 C4 1.380(4) . ?
C4 C5 1.475(4) . ?
C4 C13 1.385(4) . ?
C5 C6 1.410(4) . ?
C5 C14 1.373(3) . ?
C6 H5 0.9300 . ?
C7 C8 1.394(4) . ?
C8 C9 1.400(4) . ?
C8 C22 1.405(3) . ?
C9 H4 0.9300 . ?
C9 C10 1.351(4) . ?
C10 H2 0.9300 . ?
C10 C11 1.409(4) . ?
C11 H3 0.9300 . ?
C11 C23 1.352(4) . ?
C12 H9 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H8 0.9300 . ?
C14 C15 1.479(3) . ?
C15 C16 1.383(3) . ?
C15 C20 1.375(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 C18 1.378(4) . ?
C17 C21 1.491(4) . ?
C18 H12 0.9300 . ?
C18 C19 1.367(4) . ?
C19 H10 0.9300 . ?
C19 C20 1.373(4) . ?
C20 H11 0.9300 . ?
C21 H15 0.9600 . ?
C21 H13 0.9600 . ?
C21 H14 0.9600 . ?
C22 C23 1.409(4) . ?
C23 H17 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
C6 N1 C7 115.8(2) . . ?
N3 N2 C7 113.44(19) . . ?
N3 N2 C14 125.0(2) . . ?
C14 N2 C7 121.5(2) . . ?
C22 N3 N2 103.02(19) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C12 120.1(3) . . ?
C12 C1 H1 119.9 . . ?
C1 C2 H7 120.0 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H7 120.0 . . ?
C2 C3 H6 119.7 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H6 119.7 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 C13 118.8(3) . . ?
C13 C4 C5 121.2(2) . . ?
C6 C5 C4 118.8(2) . . ?
C14 C5 C4 123.3(2) . . ?
C14 C5 C6 117.9(2) . . ?
N1 C6 C5 125.8(2) . . ?
N1 C6 H5 117.1 . . ?
C5 C6 H5 117.1 . . ?
N1 C7 N2 122.3(2) . . ?
N1 C7 C8 132.1(2) . . ?
N2 C7 C8 105.6(2) . . ?
C7 C8 C9 134.1(2) . . ?
C7 C8 C22 104.5(2) . . ?
C9 C8 C22 121.3(2) . . ?
C8 C9 H4 121.0 . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 H4 121.0 . . ?
C9 C10 H2 119.7 . . ?
C9 C10 C11 120.7(3) . . ?
C11 C10 H2 119.7 . . ?
C10 C11 H3 118.5 . . ?
C23 C11 C10 122.9(3) . . ?
C23 C11 H3 118.5 . . ?
C1 C12 H9 120.0 . . ?
C1 C12 C13 120.1(3) . . ?
C13 C12 H9 120.0 . . ?
C4 C13 H8 119.9 . . ?
C12 C13 C4 120.2(3) . . ?
C12 C13 H8 119.9 . . ?
N2 C14 C5 116.8(2) . . ?
N2 C14 C15 119.0(2) . . ?
C5 C14 C15 124.2(2) . . ?
C16 C15 C14 121.3(2) . . ?
C20 C15 C14 119.3(2) . . ?
C20 C15 C16 119.4(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C21 121.0(3) . . ?
C18 C17 C16 118.2(3) . . ?
C18 C17 C21 120.8(2) . . ?
C17 C18 H12 119.5 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H12 119.5 . . ?
C18 C19 H10 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H10 119.8 . . ?
C15 C20 H11 120.2 . . ?
C19 C20 C15 119.7(3) . . ?
C19 C20 H11 120.2 . . ?
C17 C21 H15 109.5 . . ?
C17 C21 H13 109.5 . . ?
C17 C21 H14 109.5 . . ?
H15 C21 H13 109.5 . . ?
H15 C21 H14 109.5 . . ?
H13 C21 H14 109.5 . . ?
N3 C22 C8 113.4(2) . . ?
N3 C22 C23 126.7(2) . . ?
C8 C22 C23 119.8(2) . . ?
C11 C23 C22 117.3(3) . . ?
C11 C23 H17 121.4 . . ?
C22 C23 H17 121.4 . . ?

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 C7 C8 C9 1.4(5) . . . . ?
N1 C7 C8 C22 -178.6(3) . . . . ?
N2 N3 C22 C8 -0.3(3) . . . . ?
N2 N3 C22 C23 179.3(2) . . . . ?
N2 C7 C8 C9 -180.0(3) . . . . ?
N2 C7 C8 C22 0.1(3) . . . . ?
N2 C14 C15 C16 59.7(3) . . . . ?
N2 C14 C15 C20 -122.8(3) . . . . ?
N3 N2 C7 N1 178.5(2) . . . . ?
N3 N2 C7 C8 -0.3(3) . . . . ?
N3 N2 C14 C5 -177.7(2) . . . . ?
N3 N2 C14 C15 0.3(4) . . . . ?
N3 C22 C23 C11 -179.3(3) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C12 C13 C4 0.4(4) . . . . ?
C2 C1 C12 C13 -0.5(5) . . . . ?
C2 C3 C4 C5 -178.6(3) . . . . ?
C2 C3 C4 C13 -1.1(4) . . . . ?
C3 C4 C5 C6 60.7(3) . . . . ?
C3 C4 C5 C14 -120.8(3) . . . . ?
C3 C4 C13 C12 0.4(4) . . . . ?
C4 C5 C6 N1 177.8(3) . . . . ?
C4 C5 C14 N2 -178.4(2) . . . . ?
C4 C5 C14 C15 3.8(4) . . . . ?
C5 C4 C13 C12 177.8(2) . . . . ?
C5 C14 C15 C16 -122.5(3) . . . . ?
C5 C14 C15 C20 55.1(4) . . . . ?
C6 N1 C7 N2 -1.2(4) . . . . ?
C6 N1 C7 C8 177.3(3) . . . . ?
C6 C5 C14 N2 0.1(4) . . . . ?
C6 C5 C14 C15 -177.7(2) . . . . ?
C7 N1 C6 C5 1.3(4) . . . . ?
C7 N2 N3 C22 0.4(3) . . . . ?
C7 N2 C14 C5 -0.1(4) . . . . ?
C7 N2 C14 C15 177.9(2) . . . . ?
C7 C8 C9 C10 179.2(3) . . . . ?
C7 C8 C22 N3 0.2(3) . . . . ?
C7 C8 C22 C23 -179.5(2) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C8 C22 C23 C11 0.3(4) . . . . ?
C9 C8 C22 N3 -179.8(2) . . . . ?
C9 C8 C22 C23 0.5(4) . . . . ?
C9 C10 C11 C23 0.6(5) . . . . ?
C10 C11 C23 C22 -0.9(4) . . . . ?
C12 C1 C2 C3 -0.2(5) . . . . ?
C13 C4 C5 C6 -116.7(3) . . . . ?
C13 C4 C5 C14 61.8(4) . . . . ?
C14 N2 N3 C22 178.1(2) . . . . ?
C14 N2 C7 N1 0.7(4) . . . . ?
C14 N2 C7 C8 -178.1(2) . . . . ?
C14 C5 C6 N1 -0.8(4) . . . . ?
C14 C15 C16 C17 176.7(2) . . . . ?
C14 C15 C20 C19 -178.2(2) . . . . ?
C15 C16 C17 C18 1.4(4) . . . . ?
C15 C16 C17 C21 -178.3(3) . . . . ?
C16 C15 C20 C19 -0.6(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C15 1.5(4) . . . . ?
C20 C15 C16 C17 -0.8(4) . . . . ?
C21 C17 C18 C19 179.2(3) . . . . ?
C22 C8 C9 C10 -0.8(4) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
