# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_f046_0m_tw
_database_code_depnum_ccdc_archive 'CCDC 2384037'
loop_
_audit_author_name
_audit_author_address
'Qinghe Gao'
;Xinxiang Medical University
China
;
_audit_update_record             
;
2024-09-14 deposited with the CCDC.	2024-10-23 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         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_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                   3.989(3)
_cell_length_b                   12.220(9)
_cell_length_c                   32.27(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.740(11)
_cell_angle_gamma                90
_cell_volume                     1571(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1151
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.78
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.077
_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            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            3510
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_min         1.263
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.960
_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                2136
_reflns_number_total             3510
_reflns_special_details          
;
 _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    ?
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1590
_refine_ls_R_factor_gt           0.1161
_refine_ls_restrained_S_all      1.182
_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)+(0.1700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3128
_refine_ls_wR_factor_ref         0.3406
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.074) H11(0.061) H8(0.06) H12(0.055) H7(0.046) H6(0.049)
 H4(0.049) H5(0.061) H2(0.061) H3(0.064) H18(0.064) H10(0.07) H9(0.058)
 H15(0.07) H13(0.07) H14(0.07) H16(0.047) H17(0.049)
 Fixed X: H1(0.742807) H11(0.943878) H8(1.04335) H12(0.99808) H7(0.293869)
 H6(0.226093) H4(-0.100157) H5(0.049661) H2(0.431279) H3(0.100918)
 H18(0.479497) H10(0.523294) H9(0.499175) H15(0.863066) H13(1.175319)
 H14(1.153636) H16(0.872758) H17(0.628156)
 Fixed Y: H1(0.36862) H11(0.477872) H8(0.508676) H12(0.442376) H7(0.429562)
 H6(0.468242) H4(0.396185) H5(0.33125) H2(0.36074) H3(0.168147) H18(0.17936)
 H10(0.197742) H9(0.136362) H15(0.035233) H13(0.113277) H14(0.017882)
 H16(0.048076) H17(0.086592)
 Fixed Z: H1(0.827891) H11(0.7777) H8(0.701184) H12(0.634541) H7(0.520383)
 H6(0.435134) H4(0.438379) H5(0.376276) H2(0.385254) H3(0.408828) H18(0.397269)
 H10(0.811636) H9(0.744264) H15(0.642245) H13(0.644371) H14(0.611877)
 H16(0.546384) H17(0.474391)
;
_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
C1 C 0.7348(15) 0.3447(5) 0.80051(14) 0.0615(14) Uani 1 1 d . . . . .
H1 H 0.742807 0.368620 0.827891 0.074 Uiso 1 1 calc R U . . .
N1 N 0.5934(9) 0.3214(3) 0.57949(9) 0.0369(8) Uani 1 1 d . . . . .
C2 C 0.8520(13) 0.4101(4) 0.77063(13) 0.0511(12) Uani 1 1 d . . . . .
H11 H 0.943878 0.477872 0.777700 0.061 Uiso 1 1 calc R U . . .
N2 N 0.6853(9) 0.2322(3) 0.67927(10) 0.0389(9) Uani 1 1 d . . . . .
C3 C 0.8358(12) 0.3761(3) 0.72889(12) 0.0405(10) Uani 1 1 d . . . . .
C4 C 0.9503(13) 0.4400(4) 0.69589(13) 0.0503(12) Uani 1 1 d . . . . .
H8 H 1.043350 0.508676 0.701184 0.060 Uiso 1 1 calc R U . . .
C5 C 0.9241(13) 0.4010(3) 0.65651(13) 0.0461(11) Uani 1 1 d . . . . .
H12 H 0.998080 0.442376 0.634541 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7816(11) 0.2959(3) 0.64957(12) 0.0379(10) Uani 1 1 d . . . . .
C7 C 0.7392(11) 0.2527(3) 0.60618(12) 0.0363(9) Uani 1 1 d . . . . .
C8 C 0.5330(10) 0.2888(3) 0.53933(11) 0.0353(9) Uani 1 1 d . . . . .
C9 C 0.3647(11) 0.3615(3) 0.51135(12) 0.0381(10) Uani 1 1 d . . . . .
H7 H 0.293869 0.429562 0.520383 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3074(10) 0.3311(3) 0.47118(12) 0.0374(10) Uani 1 1 d . . . . .
C11 C 0.1412(11) 0.3939(4) 0.43594(11) 0.0405(10) Uani 1 1 d . . . . .
H6 H 0.226093 0.468242 0.435134 0.049 Uiso 1 1 calc R U . . .
H4 H -0.100157 0.396185 0.438379 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2333(13) 0.3299(4) 0.39709(13) 0.0509(12) Uani 1 1 d . . . . .
H5 H 0.049661 0.331250 0.376276 0.061 Uiso 1 1 calc R U . . .
H2 H 0.431279 0.360740 0.385254 0.061 Uiso 1 1 calc R U . . .
C13 C 0.3012(13) 0.2129(4) 0.41228(13) 0.0534(13) Uani 1 1 d . . . . .
H3 H 0.100918 0.168147 0.408828 0.064 Uiso 1 1 calc R U . . .
H18 H 0.479497 0.179360 0.397269 0.064 Uiso 1 1 calc R U . . .
C14 C 0.4038(11) 0.2260(3) 0.45733(12) 0.0393(10) Uani 1 1 d . . . . .
C15 C 0.6021(14) 0.2418(5) 0.79072(14) 0.0585(14) Uani 1 1 d . . . . .
H10 H 0.523294 0.197742 0.811636 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5868(13) 0.2052(4) 0.75060(13) 0.0487(12) Uani 1 1 d . . . . .
H9 H 0.499175 0.136362 0.744264 0.058 Uiso 1 1 calc R U . . .
C17 C 0.7045(11) 0.2723(3) 0.71903(12) 0.0380(10) Uani 1 1 d . . . . .
C18 C 0.8534(11) 0.1460(3) 0.59549(12) 0.0389(10) Uani 1 1 d . . . . .
C19 C 1.0268(12) 0.0714(4) 0.62624(13) 0.0467(11) Uani 1 1 d . . . . .
H15 H 0.863066 0.035233 0.642245 0.070 Uiso 1 1 calc R U . . .
H13 H 1.175319 0.113277 0.644371 0.070 Uiso 1 1 calc R U . . .
H14 H 1.153636 0.017882 0.611877 0.070 Uiso 1 1 calc R U . . .
C20 C 0.7982(11) 0.1162(3) 0.55489(12) 0.0394(10) Uani 1 1 d . . . . .
H16 H 0.872758 0.048076 0.546384 0.047 Uiso 1 1 calc R U . . .
C21 C 0.6333(10) 0.1847(3) 0.52564(12) 0.0364(9) Uani 1 1 d . . . . .
C22 C 0.5639(11) 0.1550(3) 0.48380(12) 0.0406(10) Uani 1 1 d . . . . .
H17 H 0.628156 0.086592 0.474391 0.049 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 H1 0.9300 . ?
C1 C2 1.353(7) . ?
C1 C15 1.394(8) . ?
N1 C7 1.318(5) . ?
N1 C8 1.366(5) . ?
C2 H11 0.9300 . ?
C2 C3 1.408(5) . ?
N2 C6 1.307(5) . ?
N2 C17 1.372(5) . ?
C3 C4 1.414(6) . ?
C3 C17 1.403(6) . ?
C4 H8 0.9300 . ?
C4 C5 1.357(6) . ?
C5 H12 0.9300 . ?
C5 C6 1.419(6) . ?
C6 C7 1.498(5) . ?
C7 C18 1.429(6) . ?
C8 C9 1.413(5) . ?
C8 C21 1.411(6) . ?
C9 H7 0.9300 . ?
C9 C10 1.358(5) . ?
C10 C11 1.500(5) . ?
C10 C14 1.419(6) . ?
C11 H6 0.9700 . ?
C11 H4 0.9700 . ?
C11 C12 1.537(6) . ?
C12 H5 0.9700 . ?
C12 H2 0.9700 . ?
C12 C13 1.532(7) . ?
C13 H3 0.9700 . ?
C13 H18 0.9700 . ?
C13 C14 1.500(5) . ?
C14 C22 1.356(6) . ?
C15 H10 0.9300 . ?
C15 C16 1.369(6) . ?
C16 H9 0.9300 . ?
C16 C17 1.405(6) . ?
C18 C19 1.492(6) . ?
C18 C20 1.368(5) . ?
C19 H15 0.9600 . ?
C19 H13 0.9600 . ?
C19 H14 0.9600 . ?
C20 H16 0.9300 . ?
C20 C21 1.402(6) . ?
C21 C22 1.412(5) . ?
C22 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
C2 C1 H1 119.6 . . ?
C2 C1 C15 120.8(4) . . ?
C15 C1 H1 119.6 . . ?
C7 N1 C8 119.1(3) . . ?
C1 C2 H11 119.8 . . ?
C1 C2 C3 120.4(5) . . ?
C3 C2 H11 119.8 . . ?
C6 N2 C17 117.9(4) . . ?
C2 C3 C4 123.7(4) . . ?
C17 C3 C2 118.9(4) . . ?
C17 C3 C4 117.3(4) . . ?
C3 C4 H8 120.1 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H8 120.1 . . ?
C4 C5 H12 120.7 . . ?
C4 C5 C6 118.6(4) . . ?
C6 C5 H12 120.7 . . ?
N2 C6 C5 123.6(4) . . ?
N2 C6 C7 116.9(4) . . ?
C5 C6 C7 119.5(4) . . ?
N1 C7 C6 114.4(3) . . ?
N1 C7 C18 124.0(4) . . ?
C18 C7 C6 121.6(3) . . ?
N1 C8 C9 118.7(4) . . ?
N1 C8 C21 121.3(4) . . ?
C21 C8 C9 120.0(3) . . ?
C8 C9 H7 120.3 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H7 120.3 . . ?
C9 C10 C11 129.2(4) . . ?
C9 C10 C14 120.8(4) . . ?
C14 C10 C11 109.9(3) . . ?
C10 C11 H6 110.9 . . ?
C10 C11 H4 110.9 . . ?
C10 C11 C12 104.1(4) . . ?
H6 C11 H4 109.0 . . ?
C12 C11 H6 110.9 . . ?
C12 C11 H4 110.9 . . ?
C11 C12 H5 110.7 . . ?
C11 C12 H2 110.7 . . ?
H5 C12 H2 108.8 . . ?
C13 C12 C11 105.1(4) . . ?
C13 C12 H5 110.7 . . ?
C13 C12 H2 110.7 . . ?
C12 C13 H3 110.9 . . ?
C12 C13 H18 110.9 . . ?
H3 C13 H18 108.9 . . ?
C14 C13 C12 104.3(3) . . ?
C14 C13 H3 110.9 . . ?
C14 C13 H18 110.9 . . ?
C10 C14 C13 109.7(4) . . ?
C22 C14 C10 120.5(4) . . ?
C22 C14 C13 129.9(4) . . ?
C1 C15 H10 119.7 . . ?
C16 C15 C1 120.6(5) . . ?
C16 C15 H10 119.7 . . ?
C15 C16 H9 120.2 . . ?
C15 C16 C17 119.6(5) . . ?
C17 C16 H9 120.2 . . ?
N2 C17 C3 122.5(4) . . ?
N2 C17 C16 117.7(4) . . ?
C3 C17 C16 119.8(4) . . ?
C7 C18 C19 122.6(4) . . ?
C20 C18 C7 115.8(4) . . ?
C20 C18 C19 121.5(4) . . ?
C18 C19 H15 109.5 . . ?
C18 C19 H13 109.5 . . ?
C18 C19 H14 109.5 . . ?
H15 C19 H13 109.5 . . ?
H15 C19 H14 109.5 . . ?
H13 C19 H14 109.5 . . ?
C18 C20 H16 118.8 . . ?
C18 C20 C21 122.4(4) . . ?
C21 C20 H16 118.8 . . ?
C8 C21 C22 119.0(4) . . ?
C20 C21 C8 117.3(4) . . ?
C20 C21 C22 123.7(4) . . ?
C14 C22 C21 120.2(4) . . ?
C14 C22 H17 119.9 . . ?
C21 C22 H17 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
C1 C2 C3 C4 179.5(5) . . . . ?
C1 C2 C3 C17 -1.7(7) . . . . ?
C1 C15 C16 C17 -0.3(8) . . . . ?
N1 C7 C18 C19 178.1(4) . . . . ?
N1 C7 C18 C20 -1.0(6) . . . . ?
N1 C8 C9 C10 179.0(4) . . . . ?
N1 C8 C21 C20 -0.2(6) . . . . ?
N1 C8 C21 C22 179.8(4) . . . . ?
C2 C1 C15 C16 -0.2(9) . . . . ?
C2 C3 C4 C5 -179.8(4) . . . . ?
C2 C3 C17 N2 -178.8(4) . . . . ?
C2 C3 C17 C16 1.1(6) . . . . ?
N2 C6 C7 N1 131.3(4) . . . . ?
N2 C6 C7 C18 -49.3(6) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C3 C17 N2 0.1(6) . . . . ?
C4 C3 C17 C16 -180.0(5) . . . . ?
C4 C5 C6 N2 -2.8(7) . . . . ?
C4 C5 C6 C7 177.9(4) . . . . ?
C5 C6 C7 N1 -49.4(6) . . . . ?
C5 C6 C7 C18 130.0(5) . . . . ?
C6 N2 C17 C3 -2.8(6) . . . . ?
C6 N2 C17 C16 177.3(4) . . . . ?
C6 C7 C18 C19 -1.2(7) . . . . ?
C6 C7 C18 C20 179.7(4) . . . . ?
C7 N1 C8 C9 177.6(4) . . . . ?
C7 N1 C8 C21 -2.1(6) . . . . ?
C7 C18 C20 C21 -1.4(6) . . . . ?
C8 N1 C7 C6 -177.9(4) . . . . ?
C8 N1 C7 C18 2.7(6) . . . . ?
C8 C9 C10 C11 -178.9(4) . . . . ?
C8 C9 C10 C14 2.2(6) . . . . ?
C8 C21 C22 C14 0.1(7) . . . . ?
C9 C8 C21 C20 -179.8(4) . . . . ?
C9 C8 C21 C22 0.2(6) . . . . ?
C9 C10 C11 C12 165.7(4) . . . . ?
C9 C10 C14 C13 178.2(4) . . . . ?
C9 C10 C14 C22 -1.8(6) . . . . ?
C10 C11 C12 C13 25.0(5) . . . . ?
C10 C14 C22 C21 0.6(6) . . . . ?
C11 C10 C14 C13 -1.0(5) . . . . ?
C11 C10 C14 C22 179.0(4) . . . . ?
C11 C12 C13 C14 -25.6(5) . . . . ?
C12 C13 C14 C10 16.8(5) . . . . ?
C12 C13 C14 C22 -163.2(5) . . . . ?
C13 C14 C22 C21 -179.4(5) . . . . ?
C14 C10 C11 C12 -15.2(5) . . . . ?
C15 C1 C2 C3 1.3(8) . . . . ?
C15 C16 C17 N2 179.8(4) . . . . ?
C15 C16 C17 C3 -0.1(7) . . . . ?
C17 N2 C6 C5 4.2(6) . . . . ?
C17 N2 C6 C7 -176.5(4) . . . . ?
C17 C3 C4 C5 1.3(7) . . . . ?
C18 C20 C21 C8 2.0(6) . . . . ?
C18 C20 C21 C22 -178.1(4) . . . . ?
C19 C18 C20 C21 179.5(4) . . . . ?
C20 C21 C22 C14 -179.8(4) . . . . ?
C21 C8 C9 C10 -1.4(6) . . . . ?

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