# Electronic Supplementary Material (ESI) 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_sust_3092_0m
_database_code_depnum_ccdc_archive 'CCDC 2314053'
loop_
_audit_author_name
_audit_author_address
imidazole
;Shaanxi Xueqian Normal University
China
;
_audit_update_record             
;
2023-12-13 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-07-19
_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         'C17 H16 N2'
_chemical_formula_sum            'C17 H16 N2'
_chemical_formula_weight         248.32
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0756(12)
_cell_length_b                   8.8912(9)
_cell_length_c                   12.8700(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.604(3)
_cell_angle_gamma                90
_cell_volume                     1380.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7394
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.7991.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      1.195
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27146
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_min         2.785
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                2106
_reflns_number_total             3225
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0926
_refine_ls_restrained_S_all      1.228
_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)+(0.0654P)²+1.2310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2366
_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.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C13(H13), C5(H5), C17(H17), C1(H1), C2(H2),
 C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_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
N2 N 0.4287(2) 0.3309(3) 0.5898(2) 0.0556(8) Uani 1 1 d . . . . .
N1 N 0.4320(2) 0.5518(4) 0.6697(2) 0.0626(8) Uani 1 1 d . . . . .
C9 C 0.2712(2) 0.3580(3) 0.4566(2) 0.0381(7) Uani 1 1 d . . . . .
C8 C 0.3480(2) 0.4182(4) 0.5394(2) 0.0423(7) Uani 1 1 d . . . . .
C10 C 0.1577(2) 0.3770(3) 0.4642(2) 0.0428(7) Uani 1 1 d . . . . .
H10 H 0.1313 0.4300 0.5203 0.051 Uiso 1 1 calc R . . . .
C11 C 0.0837(3) 0.3191(4) 0.3904(2) 0.0478(8) Uani 1 1 d . . . . .
H11 H 0.0082 0.3341 0.3971 0.057 Uiso 1 1 calc R . . . .
C7 C 0.3519(2) 0.5543(4) 0.5895(2) 0.0461(8) Uani 1 1 d . . . . .
C6 C 0.2876(3) 0.6914(4) 0.5701(2) 0.0467(8) Uani 1 1 d . . . . .
C14 C 0.3074(3) 0.2807(4) 0.3714(2) 0.0485(8) Uani 1 1 d . . . . .
H14 H 0.3830 0.2681 0.3635 0.058 Uiso 1 1 calc R . . . .
C12 C 0.1196(3) 0.2395(4) 0.3068(3) 0.0529(9) Uani 1 1 d . . . . .
C13 C 0.2326(3) 0.2221(4) 0.2980(3) 0.0553(9) Uani 1 1 d . . . . .
H13 H 0.2586 0.1698 0.2415 0.066 Uiso 1 1 calc R . . . .
C5 C 0.2490(3) 0.7318(4) 0.4716(3) 0.0622(10) Uani 1 1 d . . . . .
H5 H 0.2618 0.6690 0.4157 0.075 Uiso 1 1 calc R . . . .
C17 C 0.4750(3) 0.4172(5) 0.6659(3) 0.0666(11) Uani 1 1 d . . . . .
H17 H 0.5320 0.3843 0.7113 0.080 Uiso 1 1 calc R . . . .
C1 C 0.2661(3) 0.7877(5) 0.6512(3) 0.0656(10) Uani 1 1 d . . . . .
H1 H 0.2907 0.7628 0.7186 0.079 Uiso 1 1 calc R . . . .
C16 C 0.4566(3) 0.1747(5) 0.5712(4) 0.0762(12) Uani 1 1 d . . . . .
H16A H 0.3898 0.1175 0.5595 0.114 Uiso 1 1 calc GR . . . .
H16B H 0.4978 0.1354 0.6307 0.114 Uiso 1 1 calc GR . . . .
H16C H 0.5006 0.1680 0.5111 0.114 Uiso 1 1 calc GR . . . .
C2 C 0.2089(4) 0.9195(5) 0.6337(5) 0.0916(16) Uani 1 1 d . . . . .
H2 H 0.1957 0.9833 0.6890 0.110 Uiso 1 1 calc R . . . .
C4 C 0.1916(4) 0.8639(5) 0.4550(4) 0.0840(14) Uani 1 1 d . . . . .
H4 H 0.1664 0.8896 0.3880 0.101 Uiso 1 1 calc R . . . .
C3 C 0.1714(4) 0.9575(5) 0.5358(6) 0.0961(17) Uani 1 1 d . . . . .
H3 H 0.1323 1.0465 0.5242 0.115 Uiso 1 1 calc R . . . .
C15 C 0.0385(4) 0.1740(7) 0.2270(4) 0.0980(17) Uani 1 1 d . . . . .
H15A H -0.0358 0.1915 0.2479 0.147 Uiso 1 1 calc GR . . . .
H15B H 0.0510 0.0678 0.2213 0.147 Uiso 1 1 calc GR . . . .
H15C H 0.0483 0.2210 0.1609 0.147 Uiso 1 1 calc GR . . . .


_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
N2 C8 1.384(4) . ?
N2 C17 1.346(5) . ?
N2 C16 1.451(5) . ?
N1 C7 1.382(4) . ?
N1 C17 1.306(5) . ?
C9 C8 1.480(4) . ?
C9 C10 1.389(4) . ?
C9 C14 1.382(4) . ?
C8 C7 1.371(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(5) . ?
C7 C6 1.461(5) . ?
C6 C5 1.378(5) . ?
C6 C1 1.385(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.380(5) . ?
C12 C13 1.383(5) . ?
C12 C15 1.504(5) . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.375(6) . ?
C17 H17 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.374(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.362(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.362(7) . ?
C3 H3 0.9300 . ?
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
C8 N2 C16 128.6(3) . . ?
C17 N2 C8 106.3(3) . . ?
C17 N2 C16 125.0(3) . . ?
C17 N1 C7 104.6(3) . . ?
C10 C9 C8 119.6(3) . . ?
C14 C9 C8 122.7(3) . . ?
C14 C9 C10 117.7(3) . . ?
N2 C8 C9 122.6(3) . . ?
C7 C8 N2 105.5(3) . . ?
C7 C8 C9 131.6(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
N1 C7 C6 119.3(3) . . ?
C8 C7 N1 110.2(3) . . ?
C8 C7 C6 130.5(3) . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 C1 117.8(4) . . ?
C1 C6 C7 120.2(3) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 C15 121.0(3) . . ?
C13 C12 C15 121.0(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
N2 C17 H17 123.3 . . ?
N1 C17 N2 113.4(3) . . ?
N1 C17 H17 123.3 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.9(4) . . ?
C2 C1 H1 119.6 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.7 . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 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
N2 C8 C7 N1 -0.6(3) . . . . ?
N2 C8 C7 C6 179.0(3) . . . . ?
N1 C7 C6 C5 148.1(3) . . . . ?
N1 C7 C6 C1 -30.2(4) . . . . ?
C9 C8 C7 N1 173.2(3) . . . . ?
C9 C8 C7 C6 -7.2(5) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C9 C14 C13 C12 0.5(5) . . . . ?
C8 N2 C17 N1 0.1(4) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C8 C9 C14 C13 177.8(3) . . . . ?
C8 C7 C6 C5 -31.5(5) . . . . ?
C8 C7 C6 C1 150.3(3) . . . . ?
C10 C9 C8 N2 127.4(3) . . . . ?
C10 C9 C8 C7 -45.4(5) . . . . ?
C10 C9 C14 C13 -1.4(5) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C10 C11 C12 C15 179.0(4) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C7 N1 C17 N2 -0.5(4) . . . . ?
C7 C6 C5 C4 -177.9(3) . . . . ?
C7 C6 C1 C2 177.8(3) . . . . ?
C6 C5 C4 C3 -0.3(6) . . . . ?
C6 C1 C2 C3 0.5(6) . . . . ?
C14 C9 C8 N2 -51.7(4) . . . . ?
C14 C9 C8 C7 135.5(3) . . . . ?
C14 C9 C10 C11 1.0(4) . . . . ?
C5 C6 C1 C2 -0.5(5) . . . . ?
C5 C4 C3 C2 0.3(7) . . . . ?
C17 N2 C8 C9 -174.2(3) . . . . ?
C17 N2 C8 C7 0.3(3) . . . . ?
C17 N1 C7 C8 0.6(4) . . . . ?
C17 N1 C7 C6 -179.0(3) . . . . ?
C1 C6 C5 C4 0.4(5) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C16 N2 C8 C9 2.6(5) . . . . ?
C16 N2 C8 C7 177.0(3) . . . . ?
C16 N2 C17 N1 -176.8(3) . . . . ?
C15 C12 C13 C14 -179.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
