# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3497_0m
_database_code_depnum_ccdc_archive 'CCDC 2265600'
loop_
_audit_author_name
_audit_author_address
'Xiaofei Zhang'
;College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology
China
;
_audit_update_record             
;
2023-05-26 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2'
_chemical_formula_weight         338.43

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4607(7)
_cell_length_b                   10.9217(8)
_cell_length_c                   17.9906(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.556(2)
_cell_angle_gamma                90
_cell_volume                     1846.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    276(2)
_cell_measurement_reflns_used    4011
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      276(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 ?
_diffrn_reflns_number            52227
_diffrn_reflns_av_unetI/netI     0.1492
_diffrn_reflns_av_R_equivalents  0.5287
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_full        25.100
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3280
_reflns_number_gt                1488
_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-2018/3 (Sheldrick, 2018)'
_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)] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0202(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3280
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_restrained_S_all      0.828
_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
C1 C 0.4874(2) 0.4715(2) 0.88852(11) 0.0509(6) Uani 1 1 d . . . . .
C2 C 0.3526(2) 0.4494(2) 0.90856(11) 0.0618(7) Uani 1 1 d . . . . .
H2 H 0.306546 0.506633 0.935530 0.074 Uiso 1 1 calc R U . . .
C3 C 0.2896(2) 0.3398(2) 0.88716(12) 0.0665(7) Uani 1 1 d . . . . .
H3 H 0.200004 0.322044 0.900876 0.080 Uiso 1 1 calc R U . . .
C4 C 0.3564(2) 0.2548(2) 0.84544(12) 0.0634(6) Uani 1 1 d . . . . .
H4 H 0.310394 0.181825 0.831121 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4892(2) 0.2773(2) 0.82521(11) 0.0541(6) Uani 1 1 d . . . . .
H5 H 0.533332 0.219819 0.797457 0.065 Uiso 1 1 calc R U . . .
C6 C 0.5577(2) 0.3865(2) 0.84642(10) 0.0455(5) Uani 1 1 d . . . . .
C7 C 0.6946(2) 0.43722(19) 0.83765(10) 0.0451(5) Uani 1 1 d . . . . .
C8 C 0.7038(2) 0.5460(2) 0.87392(11) 0.0521(6) Uani 1 1 d . . . . .
C9 C 0.8282(2) 0.63095(19) 0.88106(12) 0.0651(7) Uani 1 1 d . . . . .
H9A H 0.851609 0.654720 0.932955 0.078 Uiso 1 1 calc R U . . .
H9B H 0.805128 0.704319 0.851786 0.078 Uiso 1 1 calc R U . . .
C10 C 0.9546(2) 0.56644(18) 0.85315(11) 0.0596(6) Uani 1 1 d . . . . .
H10A H 0.997657 0.511895 0.891849 0.072 Uiso 1 1 calc R U . . .
H10B H 1.025239 0.626879 0.843296 0.072 Uiso 1 1 calc R U . . .
C11 C 0.9114(2) 0.49288(19) 0.78199(10) 0.0510(6) Uani 1 1 d . . . . .
H11 H 0.857528 0.548177 0.746384 0.061 Uiso 1 1 calc R U . . .
C12 C 0.80978(19) 0.38522(17) 0.79711(10) 0.0443(5) Uani 1 1 d . . . . .
H12 H 0.765200 0.356500 0.748380 0.053 Uiso 1 1 calc R U . . .
C13 C 0.88503(19) 0.27715(18) 0.83589(12) 0.0448(5) Uani 1 1 d . . . . .
C14 C 0.8980(2) 0.2628(2) 0.91281(13) 0.0608(6) Uani 1 1 d . . . . .
H14 H 0.856403 0.319846 0.941950 0.073 Uiso 1 1 calc R U . . .
C15 C 0.9718(3) 0.1649(2) 0.94694(14) 0.0798(8) Uani 1 1 d . . . . .
H15 H 0.981015 0.157497 0.998759 0.096 Uiso 1 1 calc R U . . .
C16 C 1.0318(3) 0.0784(2) 0.90458(19) 0.0844(9) Uani 1 1 d . . . . .
H16 H 1.082072 0.012957 0.927662 0.101 Uiso 1 1 calc R U . . .
C17 C 1.0169(2) 0.0894(2) 0.82787(16) 0.0705(7) Uani 1 1 d . . . . .
H17 H 1.054947 0.030097 0.798804 0.085 Uiso 1 1 calc R U . . .
C18 C 0.9455(2) 0.1886(2) 0.79421(12) 0.0549(6) Uani 1 1 d . . . . .
H18 H 0.937698 0.196244 0.742421 0.066 Uiso 1 1 calc R U . . .
C19 C 1.0371(2) 0.41241(19) 0.67678(12) 0.0536(6) Uani 1 1 d . . . . .
C20 C 0.9226(2) 0.42586(19) 0.62184(13) 0.0638(7) Uani 1 1 d . . . . .
H20 H 0.839412 0.463271 0.633180 0.077 Uiso 1 1 calc R U . . .
C21 C 0.9327(3) 0.3832(2) 0.54988(14) 0.0751(8) Uani 1 1 d . . . . .
H21 H 0.855541 0.392788 0.513405 0.090 Uiso 1 1 calc R U . . .
C22 C 1.0535(3) 0.3275(2) 0.53136(14) 0.0768(8) Uani 1 1 d . . . . .
H22 H 1.058955 0.299040 0.483053 0.092 Uiso 1 1 calc R U . . .
C23 C 1.1665(3) 0.3148(2) 0.58592(16) 0.0758(7) Uani 1 1 d . . . . .
H23 H 1.249698 0.278020 0.573971 0.091 Uiso 1 1 calc R U . . .
C24 C 1.1595(2) 0.3550(2) 0.65769(13) 0.0667(7) Uani 1 1 d . . . . .
H24 H 1.236957 0.343906 0.693811 0.080 Uiso 1 1 calc R U . . .
N1 N 0.57864(19) 0.56863(16) 0.90381(9) 0.0605(5) Uani 1 1 d . . . . .
H1 H 0.560393 0.633360 0.928216 0.073 Uiso 1 1 calc R U . . .
N2 N 1.03704(16) 0.45630(15) 0.74903(9) 0.0588(5) Uani 1 1 d . . . . .
H2A H 1.117636 0.462175 0.776220 0.071 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
C1 N1 1.376(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.411(3) . ?
C2 C3 1.372(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.370(2) . ?
C5 C6 1.390(3) . ?
C6 C7 1.434(3) . ?
C7 C8 1.354(2) . ?
C7 C12 1.491(3) . ?
C8 N1 1.378(2) . ?
C8 C9 1.492(3) . ?
C9 C10 1.522(3) . ?
C10 C11 1.527(2) . ?
C11 N2 1.444(2) . ?
C11 C12 1.562(3) . ?
C12 C13 1.508(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.387(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.376(3) . ?
C17 C18 1.380(3) . ?
C19 N2 1.386(2) . ?
C19 C20 1.388(3) . ?
C19 C24 1.394(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.369(3) . ?
C22 C23 1.373(3) . ?
C23 C24 1.373(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 131.1(2) . . ?
N1 C1 C6 106.90(19) . . ?
C2 C1 C6 122.0(2) . . ?
C3 C2 C1 117.5(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 120.7(2) . . ?
C4 C5 C6 119.6(2) . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 134.4(2) . . ?
C1 C6 C7 107.00(19) . . ?
C8 C7 C6 107.16(19) . . ?
C8 C7 C12 124.05(19) . . ?
C6 C7 C12 128.79(19) . . ?
C7 C8 N1 109.55(19) . . ?
C7 C8 C9 126.4(2) . . ?
N1 C8 C9 124.0(2) . . ?
C8 C9 C10 109.00(18) . . ?
C9 C10 C11 112.04(16) . . ?
N2 C11 C10 109.62(16) . . ?
N2 C11 C12 114.52(17) . . ?
C10 C11 C12 111.17(17) . . ?
C7 C12 C13 113.87(17) . . ?
C7 C12 C11 107.28(16) . . ?
C13 C12 C11 113.72(15) . . ?
C14 C13 C18 117.82(19) . . ?
C14 C13 C12 122.3(2) . . ?
C18 C13 C12 119.86(19) . . ?
C15 C14 C13 121.0(2) . . ?
C16 C15 C14 120.3(2) . . ?
C17 C16 C15 119.6(2) . . ?
C16 C17 C18 119.8(2) . . ?
C17 C18 C13 121.5(2) . . ?
N2 C19 C20 123.2(2) . . ?
N2 C19 C24 118.45(19) . . ?
C20 C19 C24 118.4(2) . . ?
C19 C20 C21 119.8(2) . . ?
C22 C21 C20 121.6(2) . . ?
C21 C22 C23 118.3(3) . . ?
C24 C23 C22 121.5(3) . . ?
C23 C24 C19 120.4(2) . . ?
C1 N1 C8 109.37(18) . . ?
C19 N2 C11 124.73(16) . . ?

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 C3 -177.29(19) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 177.43(19) . . . . ?
N1 C1 C6 C5 178.29(16) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N1 C1 C6 C7 0.2(2) . . . . ?
C2 C1 C6 C7 -178.59(17) . . . . ?
C5 C6 C7 C8 -176.9(2) . . . . ?
C1 C6 C7 C8 0.7(2) . . . . ?
C5 C6 C7 C12 3.2(3) . . . . ?
C1 C6 C7 C12 -179.21(18) . . . . ?
C6 C7 C8 N1 -1.4(2) . . . . ?
C12 C7 C8 N1 178.54(16) . . . . ?
C6 C7 C8 C9 178.96(17) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C10 -10.1(3) . . . . ?
N1 C8 C9 C10 170.34(17) . . . . ?
C8 C9 C10 C11 41.7(2) . . . . ?
C9 C10 C11 N2 167.48(17) . . . . ?
C9 C10 C11 C12 -64.9(2) . . . . ?
C8 C7 C12 C13 108.2(2) . . . . ?
C6 C7 C12 C13 -71.9(2) . . . . ?
C8 C7 C12 C11 -18.6(2) . . . . ?
C6 C7 C12 C11 161.39(17) . . . . ?
N2 C11 C12 C7 174.51(15) . . . . ?
C10 C11 C12 C7 49.6(2) . . . . ?
N2 C11 C12 C13 47.7(2) . . . . ?
C10 C11 C12 C13 -77.3(2) . . . . ?
C7 C12 C13 C14 -29.0(3) . . . . ?
C11 C12 C13 C14 94.3(2) . . . . ?
C7 C12 C13 C18 151.71(18) . . . . ?
C11 C12 C13 C18 -85.0(2) . . . . ?
C18 C13 C14 C15 1.6(3) . . . . ?
C12 C13 C14 C15 -177.75(19) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C18 1.8(4) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C12 C13 C18 C17 179.06(17) . . . . ?
N2 C19 C20 C21 177.66(18) . . . . ?
C24 C19 C20 C21 -0.5(3) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C24 0.8(4) . . . . ?
C22 C23 C24 C19 -1.2(3) . . . . ?
N2 C19 C24 C23 -177.24(18) . . . . ?
C20 C19 C24 C23 1.0(3) . . . . ?
C2 C1 N1 C8 177.57(19) . . . . ?
C6 C1 N1 C8 -1.1(2) . . . . ?
C7 C8 N1 C1 1.6(2) . . . . ?
C9 C8 N1 C1 -178.77(17) . . . . ?
C20 C19 N2 C11 16.1(3) . . . . ?
C24 C19 N2 C11 -165.71(19) . . . . ?
C10 C11 N2 C19 -165.20(17) . . . . ?
C12 C11 N2 C19 69.1(2) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.103



