# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_phy325
_database_code_depnum_ccdc_archive 'CCDC 2539500'
loop_
_audit_author_name
_audit_author_address
'haoyu peng'
;Soochow University
China
;
_audit_update_record             
;
2026-03-25 deposited with the CCDC.	2026-06-16 downloaded from the CCDC.
;
_audit_creation_date             2026-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7530)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N'
_chemical_formula_sum            'C20 H19 N'
_chemical_formula_weight         273.36
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0064(2)
_cell_length_b                   10.9329(4)
_cell_length_c                   23.1967(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1523.27(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8668
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.069
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17746
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.059
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3164
_reflns_number_total             3500
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      0.978
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16), C17(H17), C18(H18), C19(H19), C2(H2), C8(H8), C7(H7),
 C3(H3), C5(H5), C4(H4)
2.c X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
;
_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
N1 N 0.6716(3) 0.88742(13) 0.34075(7) 0.0404(4) Uani 1 1 d . . . . .
C15 C 0.5078(3) 0.40561(16) 0.45571(8) 0.0369(4) Uani 1 1 d . . . . .
C9 C 0.4958(3) 0.82541(16) 0.32308(9) 0.0412(4) Uani 1 1 d . . . . .
C20 C 0.3443(3) 0.31604(18) 0.45419(8) 0.0413(4) Uani 1 1 d . . . . .
H20 H 0.206369 0.330516 0.472055 0.050 Uiso 1 1 calc R U . . .
C1 C 0.8063(3) 0.94063(16) 0.30032(8) 0.0391(4) Uani 1 1 d . . . . .
C12 C 0.3384(3) 0.61680(16) 0.45241(8) 0.0401(4) Uani 1 1 d . . . . .
C6 C 0.7649(3) 0.93128(17) 0.24030(8) 0.0442(5) Uani 1 1 d . . . . .
C16 C 0.7087(3) 0.38278(18) 0.42794(8) 0.0419(4) Uani 1 1 d . . . . .
H16 H 0.820826 0.442765 0.428027 0.050 Uiso 1 1 calc R U . . .
C11 C 0.4624(3) 0.66875(17) 0.40164(9) 0.0411(4) Uani 1 1 d . . . . .
H11A H 0.490696 0.602104 0.374352 0.049 Uiso 1 1 calc R U . . .
H11B H 0.607323 0.698060 0.415264 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7451(3) 0.27231(19) 0.40013(9) 0.0473(5) Uani 1 1 d . . . . .
H17 H 0.881399 0.258267 0.381338 0.057 Uiso 1 1 calc R U . . .
C18 C 0.5835(3) 0.18298(19) 0.39977(9) 0.0480(5) Uani 1 1 d . . . . .
H18 H 0.609701 0.107603 0.381490 0.058 Uiso 1 1 calc R U . . .
C19 C 0.3819(3) 0.20562(18) 0.42668(9) 0.0464(5) Uani 1 1 d . . . . .
H19 H 0.269869 0.145608 0.426259 0.056 Uiso 1 1 calc R U . . .
C14 C 0.4666(3) 0.52421(18) 0.48745(8) 0.0442(5) Uani 1 1 d . . . . .
H14A H 0.383681 0.506656 0.522891 0.053 Uiso 1 1 calc R U . . .
H14B H 0.610095 0.559768 0.498536 0.053 Uiso 1 1 calc R U . . .
C2 C 0.9898(3) 1.01005(18) 0.31909(10) 0.0480(5) Uani 1 1 d . . . . .
H2 H 1.020119 1.015855 0.358753 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4463(4) 0.8096(2) 0.26387(10) 0.0515(5) Uani 1 1 d . . . . .
H8 H 0.322524 0.762635 0.252684 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3501(3) 0.77243(18) 0.36909(10) 0.0464(5) Uani 1 1 d . . . . .
H10A H 0.212596 0.741880 0.351465 0.056 Uiso 1 1 calc R U . . .
H10B H 0.309531 0.837087 0.396406 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5776(4) 0.86240(19) 0.22328(9) 0.0533(5) Uani 1 1 d . . . . .
H7 H 0.543827 0.853070 0.183955 0.064 Uiso 1 1 calc R U . . .
C13 C 0.1331(3) 0.64881(19) 0.46688(10) 0.0540(5) Uani 1 1 d . . . . .
H13A H 0.056107 0.707340 0.444887 0.065 Uiso 1 1 calc R U . . .
H13B H 0.064434 0.612991 0.499149 0.065 Uiso 1 1 calc R U . . .
C3 C 1.1240(4) 1.0689(2) 0.28085(12) 0.0591(6) Uani 1 1 d . . . . .
H3 H 1.245011 1.115297 0.294347 0.071 Uiso 1 1 calc R U . . .
C5 C 0.9098(4) 0.9925(2) 0.20173(10) 0.0586(6) Uani 1 1 d . . . . .
H5 H 0.885898 0.985795 0.161800 0.070 Uiso 1 1 calc R U . . .
C4 C 1.0832(4) 1.0609(2) 0.22159(12) 0.0628(6) Uani 1 1 d . . . . .
H4 H 1.175485 1.102714 0.195461 0.075 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 C9 1.320(2) . ?
N1 C1 1.368(2) . ?
C15 C20 1.387(3) . ?
C15 C16 1.390(3) . ?
C15 C14 1.512(2) . ?
C9 C8 1.416(3) . ?
C9 C10 1.497(3) . ?
C20 H20 0.9400 . ?
C20 C19 1.384(3) . ?
C1 C6 1.418(3) . ?
C1 C2 1.407(3) . ?
C12 C11 1.505(3) . ?
C12 C14 1.509(3) . ?
C12 C13 1.325(3) . ?
C6 C7 1.410(3) . ?
C6 C5 1.416(3) . ?
C16 H16 0.9400 . ?
C16 C17 1.387(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C10 1.520(3) . ?
C17 H17 0.9400 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9400 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C2 H2 0.9400 . ?
C2 C3 1.361(3) . ?
C8 H8 0.9400 . ?
C8 C7 1.357(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C7 H7 0.9400 . ?
C13 H13A 0.9400 . ?
C13 H13B 0.9400 . ?
C3 H3 0.9400 . ?
C3 C4 1.399(4) . ?
C5 H5 0.9400 . ?
C5 C4 1.363(4) . ?
C4 H4 0.9400 . ?

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
C9 N1 C1 118.59(17) . . ?
C20 C15 C16 118.41(17) . . ?
C20 C15 C14 120.13(16) . . ?
C16 C15 C14 121.46(17) . . ?
N1 C9 C8 122.13(19) . . ?
N1 C9 C10 116.43(17) . . ?
C8 C9 C10 121.44(18) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.80(18) . . ?
C19 C20 H20 119.6 . . ?
N1 C1 C6 122.59(18) . . ?
N1 C1 C2 118.71(17) . . ?
C2 C1 C6 118.68(18) . . ?
C11 C12 C14 114.97(16) . . ?
C13 C12 C11 124.0(2) . . ?
C13 C12 C14 121.0(2) . . ?
C7 C6 C1 116.95(19) . . ?
C7 C6 C5 124.4(2) . . ?
C5 C6 C1 118.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.58(17) . . ?
C17 C16 H16 119.7 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C12 C11 C10 116.78(16) . . ?
H11A C11 H11B 107.3 . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.62(18) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.14(19) . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 120.43(19) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C12 C14 C15 113.36(15) . . ?
C12 C14 H14A 108.9 . . ?
C12 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 119.94(19) . . ?
C7 C8 H8 120.0 . . ?
C9 C10 C11 112.53(16) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.77(19) . . ?
C8 C7 H7 120.1 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?

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 C9 C8 C7 -2.1(3) . . . . ?
N1 C9 C10 C11 -69.0(2) . . . . ?
N1 C1 C6 C7 -0.8(3) . . . . ?
N1 C1 C6 C5 178.14(17) . . . . ?
N1 C1 C2 C3 -177.39(19) . . . . ?
C15 C20 C19 C18 -0.5(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C9 N1 C1 C6 -0.3(3) . . . . ?
C9 N1 C1 C2 178.00(16) . . . . ?
C9 C8 C7 C6 0.9(3) . . . . ?
C20 C15 C16 C17 -0.9(3) . . . . ?
C20 C15 C14 C12 -82.7(2) . . . . ?
C1 N1 C9 C8 1.8(3) . . . . ?
C1 N1 C9 C10 -178.12(15) . . . . ?
C1 C6 C7 C8 0.4(3) . . . . ?
C1 C6 C5 C4 -1.2(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C12 C11 C10 C9 174.53(17) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C6 C5 C4 C3 1.7(3) . . . . ?
C16 C15 C20 C19 1.3(3) . . . . ?
C16 C15 C14 C12 97.8(2) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C11 C12 C14 C15 -68.4(2) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C14 C15 C20 C19 -178.18(17) . . . . ?
C14 C15 C16 C17 178.57(17) . . . . ?
C14 C12 C11 C10 -173.38(16) . . . . ?
C2 C1 C6 C7 -179.10(17) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C8 C9 C10 C11 111.2(2) . . . . ?
C10 C9 C8 C7 177.73(18) . . . . ?
C7 C6 C5 C4 177.7(2) . . . . ?
C13 C12 C11 C10 5.9(3) . . . . ?
C13 C12 C14 C15 112.3(2) . . . . ?
C5 C6 C7 C8 -178.45(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
