# Supplementary Information (SI) for Chemical Science.
# 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_409
_database_code_depnum_ccdc_archive 'CCDC 2429896'
loop_
_audit_author_name
_audit_author_address
'Yang Liu'
;Anhui university
China
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
_audit_creation_date             2022-03-29
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_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'
O O 0.0106 0.0060 '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                   9.5496(7)
_cell_length_b                   10.1080(8)
_cell_length_c                   17.3620(16)
_cell_angle_alpha                90.483(7)
_cell_angle_beta                 97.956(7)
_cell_angle_gamma                100.119(6)
_cell_volume                     1633.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3870
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      26.9130
_cell_measurement_theta_min      2.0750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1252
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5743
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.039
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_min         2.048
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  85.00   1.00    6.00    --   11.90  57.00  60.00   99
  2  ω     35.00  61.00   1.00    6.00    --   11.90 178.00-120.00   26
  3  ω    -14.00  78.00   1.00    6.00    --   11.90  77.00-180.00   92
  4  ω    -55.00  38.00   1.00    6.00    --   11.90 -57.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205972000
_diffrn_orient_matrix_UB_12      -0.0155691000
_diffrn_orient_matrix_UB_13      0.0370504000
_diffrn_orient_matrix_UB_21      0.0537493000
_diffrn_orient_matrix_UB_22      0.0534923000
_diffrn_orient_matrix_UB_23      0.0173014000
_diffrn_orient_matrix_UB_31      -0.0499669000
_diffrn_orient_matrix_UB_32      0.0445295000
_diffrn_orient_matrix_UB_33      -0.0056093000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3953
_reflns_number_total             5743
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5743
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.1126
_refine_ls_restrained_S_all      1.080
_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)+(0.1342P)²+2.2491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2851
_refine_ls_wR_factor_ref         0.3080
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.679(7)
 0.321(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C35(H35), C9(H9), C34(H34), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C26(H26A,H26B), C37(H37A,H37B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C6(H6), C17(H17), C2(H2), C25(H25), C24(H24), C23(H23), C14(H14),
 C32(H32), C31(H31), C22(H22), C30(H30), C29(H29), C16(H16), C15(H15), C4(H4),
 C5(H5), C3(H3)
3.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O4 O 1.1351(4) 0.7676(4) 0.7110(2) 0.0408(9) Uani 1 1 d . . . . .
O6 O 1.1072(4) 1.0044(4) 0.4383(2) 0.0451(10) Uani 1 1 d . . . . .
O5 O 1.3710(4) 1.0061(4) 0.5862(2) 0.0391(9) Uani 1 1 d . . . . .
O1 O 0.4834(4) 0.7439(4) 0.2155(2) 0.0457(10) Uani 1 1 d . . . . .
O3 O 0.1798(4) 0.5103(4) 0.0812(2) 0.0391(9) Uani 1 1 d . . . . .
N1 N 0.6077(4) 0.8536(4) 0.1244(2) 0.0301(9) Uani 1 1 d . . . . .
N4 N 1.1008(4) 0.7991(4) 0.5027(2) 0.0295(9) Uani 1 1 d . . . . .
N2 N 0.4092(4) 0.7179(4) 0.0063(2) 0.0316(10) Uani 1 1 d . . . . .
N3 N 0.9650(4) 0.6589(4) 0.6153(2) 0.0301(10) Uani 1 1 d . . . . .
O2 O 0.3635(5) 0.5164(4) -0.0688(2) 0.0514(11) Uani 1 1 d . . . . .
C12 C 0.5248(5) 0.8116(5) -0.0154(3) 0.0310(11) Uani 1 1 d . . . . .
C33 C 1.0912(5) 0.7441(5) 0.6420(3) 0.0307(11) Uani 1 1 d . . . . .
C27 C 0.9079(5) 0.6324(5) 0.5346(3) 0.0286(11) Uani 1 1 d . . . . .
C20 C 0.7490(5) 0.6341(5) 0.6852(3) 0.0298(11) Uani 1 1 d . . . . .
C1 C 0.8567(5) 0.8687(5) 0.1969(3) 0.0299(11) Uani 1 1 d . . . . .
C7 C 0.7175(5) 0.9226(5) 0.1870(3) 0.0327(11) Uani 1 1 d . . . . .
H7A H 0.678207 0.914720 0.235672 0.039 Uiso 1 1 calc R U . . .
H7B H 0.738194 1.017434 0.176044 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4931(5) 0.7685(5) 0.1473(3) 0.0303(11) Uani 1 1 d . . . . .
C35 C 1.2216(5) 0.9564(5) 0.5759(3) 0.0354(12) Uani 1 1 d . . . . .
H35 H 1.172537 1.004404 0.610171 0.042 Uiso 1 1 calc R U . . .
C21 C 0.6520(6) 0.5543(6) 0.7254(3) 0.0382(13) Uani 1 1 d . . . . .
H21 H 0.671123 0.471662 0.742832 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9824(6) 0.9484(5) 0.2336(3) 0.0338(12) Uani 1 1 d . . . . .
H6 H 0.981022 1.036002 0.249886 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5405(6) 0.8327(5) -0.0925(3) 0.0386(13) Uani 1 1 d . . . . .
H17 H 0.471850 0.788202 -0.131816 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3705(6) 0.7111(5) 0.0848(3) 0.0347(12) Uani 1 1 d . . . . .
H9 H 0.286973 0.753947 0.088009 0.042 Uiso 1 1 calc R U . . .
C26 C 0.8875(6) 0.5864(5) 0.6740(3) 0.0353(12) Uani 1 1 d . . . . .
H26A H 0.950375 0.596083 0.723424 0.042 Uiso 1 1 calc R U . . .
H26B H 0.865022 0.491552 0.659172 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6244(5) 0.8787(5) 0.0453(3) 0.0304(11) Uani 1 1 d . . . . .
C2 C 0.8624(6) 0.7380(5) 0.1725(3) 0.0407(13) Uani 1 1 d . . . . .
H2 H 0.779901 0.682532 0.147914 0.049 Uiso 1 1 calc R U . . .
C36 C 1.1378(6) 0.9352(5) 0.4932(3) 0.0371(12) Uani 1 1 d . . . . .
C34 C 1.1805(6) 0.8036(5) 0.5818(3) 0.0330(12) Uani 1 1 d . . . . .
H34 H 1.265231 0.761051 0.582189 0.040 Uiso 1 1 calc R U . . .
C25 C 0.7174(6) 0.7556(5) 0.6575(3) 0.0378(13) Uani 1 1 d . . . . .
H25 H 0.780484 0.809625 0.629621 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5910(6) 0.7961(6) 0.6715(3) 0.0428(14) Uani 1 1 d . . . . .
H24 H 0.569876 0.877482 0.653114 0.051 Uiso 1 1 calc R U . . .
C23 C 0.4966(6) 0.7158(6) 0.7129(3) 0.0392(13) Uani 1 1 d . . . . .
H23 H 0.412521 0.743532 0.722276 0.047 Uiso 1 1 calc R U . . .
C28 C 0.9761(5) 0.7038(5) 0.4765(3) 0.0293(11) Uani 1 1 d . . . . .
C14 C 0.7426(6) 0.9656(5) 0.0252(3) 0.0391(13) Uani 1 1 d . . . . .
H14 H 0.811224 1.011302 0.064081 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3638(6) 0.5826(6) -0.0105(3) 0.0381(13) Uani 1 1 d . . . . .
C32 C 0.7841(6) 0.5415(5) 0.5112(3) 0.0396(13) Uani 1 1 d . . . . .
H32 H 0.737445 0.492386 0.548204 0.048 Uiso 1 1 calc R U . . .
C31 C 0.7274(6) 0.5218(5) 0.4327(3) 0.0421(13) Uani 1 1 d . . . . .
H31 H 0.641796 0.462031 0.417972 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3247(6) 0.5591(5) 0.0720(3) 0.0377(12) Uani 1 1 d . . . . .
H10 H 0.390913 0.509982 0.103203 0.045 Uiso 1 1 calc R U . . .
C22 C 0.5267(6) 0.5956(6) 0.7399(3) 0.0425(14) Uani 1 1 d . . . . .
H22 H 0.463598 0.541905 0.767904 0.051 Uiso 1 1 calc R U . . .
C30 C 0.7966(6) 0.5897(6) 0.3773(3) 0.0430(14) Uani 1 1 d . . . . .
H30 H 0.759514 0.573606 0.324940 0.052 Uiso 1 1 calc R U . . .
C29 C 0.9229(6) 0.6832(5) 0.3985(3) 0.0354(12) Uani 1 1 d . . . . .
H29 H 0.969841 0.730462 0.360998 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6595(7) 0.9208(6) -0.1111(3) 0.0437(14) Uani 1 1 d . . . . .
H16 H 0.670993 0.936042 -0.162800 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7594(7) 0.9847(5) -0.0522(4) 0.0444(14) Uani 1 1 d . . . . .
H15 H 0.840090 1.042159 -0.064375 0.053 Uiso 1 1 calc R U . . .
C4 C 1.1144(7) 0.7704(6) 0.2212(3) 0.0449(14) Uani 1 1 d . . . . .
H4 H 1.200513 0.738156 0.228993 0.054 Uiso 1 1 calc R U . . .
C5 C 1.1096(6) 0.8985(6) 0.2461(3) 0.0426(14) Uani 1 1 d . . . . .
H5 H 1.192435 0.952303 0.271653 0.051 Uiso 1 1 calc R U . . .
C3 C 0.9930(7) 0.6908(6) 0.1850(4) 0.0509(16) Uani 1 1 d . . . . .
H3 H 0.996576 0.603898 0.168447 0.061 Uiso 1 1 calc R U . . .
C37 C 1.4013(7) 1.1497(6) 0.5821(5) 0.0553(17) Uani 1 1 d . . . . .
H37A H 1.367182 1.190354 0.625103 0.066 Uiso 1 1 calc R U . . .
H37B H 1.351743 1.177029 0.533932 0.066 Uiso 1 1 calc R U . . .
C18 C 0.1472(8) 0.3652(6) 0.0683(5) 0.068(2) Uani 1 1 d . . . . .
H18A H 0.160603 0.342595 0.015715 0.082 Uiso 1 1 calc R U . . .
H18B H 0.212313 0.323558 0.104180 0.082 Uiso 1 1 calc R U . . .
C38 C 1.5550(9) 1.1949(8) 0.5857(6) 0.079(2) Uani 1 1 d . . . . .
H38A H 1.587032 1.159817 0.540942 0.118 Uiso 1 1 calc R U . . .
H38B H 1.603963 1.163304 0.632084 0.118 Uiso 1 1 calc R U . . .
H38C H 1.575721 1.291329 0.586385 0.118 Uiso 1 1 calc R U . . .
C19 C 0.0006(10) 0.3146(8) 0.0797(6) 0.086(3) Uani 1 1 d . . . . .
H19A H -0.010515 0.331470 0.132829 0.129 Uiso 1 1 calc R U . . .
H19B H -0.021726 0.219569 0.068072 0.129 Uiso 1 1 calc R U . . .
H19C H -0.063235 0.359074 0.045854 0.129 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
O4 C33 1.221(6) . ?
O6 C36 1.219(6) . ?
O5 C35 1.413(6) . ?
O5 C37 1.433(7) . ?
O1 C8 1.225(6) . ?
O3 C10 1.416(6) . ?
O3 C18 1.453(7) . ?
N1 C7 1.477(6) . ?
N1 C8 1.375(6) . ?
N1 C13 1.424(6) . ?
N4 C36 1.377(7) . ?
N4 C34 1.472(6) . ?
N4 C28 1.412(6) . ?
N2 C12 1.418(6) . ?
N2 C9 1.460(6) . ?
N2 C11 1.377(7) . ?
N3 C33 1.372(7) . ?
N3 C27 1.436(6) . ?
N3 C26 1.468(6) . ?
O2 C11 1.208(7) . ?
C12 C17 1.382(7) . ?
C12 C13 1.400(7) . ?
C33 C34 1.502(7) . ?
C27 C28 1.411(7) . ?
C27 C32 1.374(7) . ?
C20 C21 1.386(7) . ?
C20 C26 1.520(7) . ?
C20 C25 1.389(7) . ?
C1 C7 1.511(7) . ?
C1 C6 1.391(7) . ?
C1 C2 1.397(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.510(7) . ?
C35 H35 0.9800 . ?
C35 C36 1.539(8) . ?
C35 C34 1.534(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.393(8) . ?
C9 H9 0.9800 . ?
C9 C10 1.527(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C13 C14 1.390(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.402(8) . ?
C34 H34 0.9800 . ?
C25 H25 0.9300 . ?
C25 C24 1.392(8) . ?
C24 H24 0.9300 . ?
C24 C23 1.385(8) . ?
C23 H23 0.9300 . ?
C23 C22 1.369(8) . ?
C28 C29 1.379(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(8) . ?
C11 C10 1.539(8) . ?
C32 H32 0.9300 . ?
C32 C31 1.395(8) . ?
C31 H31 0.9300 . ?
C31 C30 1.364(8) . ?
C10 H10 0.9800 . ?
C22 H22 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.398(8) . ?
C29 H29 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.369(9) . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.372(9) . ?
C4 C3 1.360(9) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.451(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.445(11) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C35 O5 C37 111.5(4) . . ?
C10 O3 C18 109.9(5) . . ?
C8 N1 C7 116.7(4) . . ?
C8 N1 C13 124.0(4) . . ?
C13 N1 C7 119.4(4) . . ?
C36 N4 C34 94.2(4) . . ?
C36 N4 C28 132.9(4) . . ?
C28 N4 C34 123.7(4) . . ?
C12 N2 C9 123.8(4) . . ?
C11 N2 C12 132.1(4) . . ?
C11 N2 C9 94.4(4) . . ?
C33 N3 C27 124.5(4) . . ?
C33 N3 C26 116.9(4) . . ?
C27 N3 C26 118.6(4) . . ?
C17 C12 N2 121.7(5) . . ?
C17 C12 C13 121.7(5) . . ?
C13 C12 N2 116.6(4) . . ?
O4 C33 N3 123.1(5) . . ?
O4 C33 C34 119.9(5) . . ?
N3 C33 C34 116.8(4) . . ?
C28 C27 N3 120.3(4) . . ?
C32 C27 N3 122.0(4) . . ?
C32 C27 C28 117.7(5) . . ?
C21 C20 C26 118.7(4) . . ?
C21 C20 C25 119.0(5) . . ?
C25 C20 C26 122.3(4) . . ?
C6 C1 C7 119.9(4) . . ?
C6 C1 C2 118.3(5) . . ?
C2 C1 C7 121.7(4) . . ?
N1 C7 C1 114.3(4) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7A 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 123.0(5) . . ?
O1 C8 C9 119.5(4) . . ?
N1 C8 C9 117.3(4) . . ?
O5 C35 H35 111.5 . . ?
O5 C35 C36 119.6(4) . . ?
O5 C35 C34 114.6(4) . . ?
C36 C35 H35 111.5 . . ?
C34 C35 H35 111.5 . . ?
C34 C35 C36 85.6(4) . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.1(5) . . ?
C22 C21 H21 119.5 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.7(5) . . ?
C5 C6 H6 119.7 . . ?
C12 C17 H17 120.1 . . ?
C12 C17 C16 119.7(5) . . ?
C16 C17 H17 120.1 . . ?
N2 C9 C8 113.7(4) . . ?
N2 C9 H9 110.7 . . ?
N2 C9 C10 88.7(4) . . ?
C8 C9 H9 110.7 . . ?
C8 C9 C10 120.4(5) . . ?
C10 C9 H9 110.7 . . ?
N3 C26 C20 114.3(4) . . ?
N3 C26 H26A 108.7 . . ?
N3 C26 H26B 108.7 . . ?
C20 C26 H26A 108.7 . . ?
C20 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C12 C13 N1 120.8(4) . . ?
C14 C13 N1 121.8(5) . . ?
C14 C13 C12 117.4(5) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
O6 C36 N4 130.7(5) . . ?
O6 C36 C35 137.5(5) . . ?
N4 C36 C35 91.7(4) . . ?
N4 C34 C33 114.1(4) . . ?
N4 C34 C35 88.4(4) . . ?
N4 C34 H34 110.5 . . ?
C33 C34 C35 120.8(5) . . ?
C33 C34 H34 110.5 . . ?
C35 C34 H34 110.5 . . ?
C20 C25 H25 120.1 . . ?
C20 C25 C24 119.8(5) . . ?
C24 C25 H25 120.1 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.3(5) . . ?
C23 C24 H24 119.8 . . ?
C24 C23 H23 119.9 . . ?
C22 C23 C24 120.2(5) . . ?
C22 C23 H23 119.9 . . ?
C27 C28 N4 116.2(4) . . ?
C29 C28 N4 121.8(4) . . ?
C29 C28 C27 122.0(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
N2 C11 C10 91.3(4) . . ?
O2 C11 N2 130.7(5) . . ?
O2 C11 C10 137.9(5) . . ?
C27 C32 H32 119.5 . . ?
C27 C32 C31 120.9(5) . . ?
C31 C32 H32 119.5 . . ?
C32 C31 H31 119.8 . . ?
C30 C31 C32 120.5(5) . . ?
C30 C31 H31 119.8 . . ?
O3 C10 C9 114.2(5) . . ?
O3 C10 C11 119.2(4) . . ?
O3 C10 H10 111.8 . . ?
C9 C10 C11 85.5(4) . . ?
C9 C10 H10 111.8 . . ?
C11 C10 H10 111.8 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.2 . . ?
C31 C30 H30 119.8 . . ?
C31 C30 C29 120.5(5) . . ?
C29 C30 H30 119.8 . . ?
C28 C29 C30 118.4(5) . . ?
C28 C29 H29 120.8 . . ?
C30 C29 H29 120.8 . . ?
C17 C16 H16 120.5 . . ?
C15 C16 C17 119.1(5) . . ?
C15 C16 H16 120.5 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.3(5) . . ?
C16 C15 H15 119.4 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
O5 C37 H37A 109.8 . . ?
O5 C37 H37B 109.8 . . ?
O5 C37 C38 109.6(6) . . ?
H37A C37 H37B 108.2 . . ?
C38 C37 H37A 109.8 . . ?
C38 C37 H37B 109.8 . . ?
O3 C18 H18A 109.7 . . ?
O3 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 O3 110.0(6) . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O4 C33 C34 N4 -164.0(4) . . . . ?
O4 C33 C34 C35 -60.6(7) . . . . ?
O5 C35 C36 O6 -64.3(9) . . . . ?
O5 C35 C36 N4 117.5(5) . . . . ?
O5 C35 C34 N4 -122.1(5) . . . . ?
O5 C35 C34 C33 120.5(5) . . . . ?
O1 C8 C9 N2 -165.0(5) . . . . ?
O1 C8 C9 C10 -61.8(7) . . . . ?
N1 C8 C9 N2 19.0(7) . . . . ?
N1 C8 C9 C10 122.2(5) . . . . ?
N1 C13 C14 C15 177.6(5) . . . . ?
N4 C28 C29 C30 -178.3(5) . . . . ?
N2 C12 C17 C16 -176.9(5) . . . . ?
N2 C12 C13 N1 -0.6(7) . . . . ?
N2 C12 C13 C14 176.6(4) . . . . ?
N2 C9 C10 O3 -122.4(5) . . . . ?
N2 C9 C10 C11 -2.3(4) . . . . ?
N2 C11 C10 O3 117.7(5) . . . . ?
N2 C11 C10 C9 2.5(4) . . . . ?
N3 C33 C34 N4 19.2(6) . . . . ?
N3 C33 C34 C35 122.6(5) . . . . ?
N3 C27 C28 N4 0.4(6) . . . . ?
N3 C27 C28 C29 -178.6(5) . . . . ?
N3 C27 C32 C31 177.2(5) . . . . ?
O2 C11 C10 O3 -64.6(9) . . . . ?
O2 C11 C10 C9 -179.8(7) . . . . ?
C12 N2 C9 C8 -23.8(7) . . . . ?
C12 N2 C9 C10 -146.6(5) . . . . ?
C12 N2 C11 O2 -35.5(9) . . . . ?
C12 N2 C11 C10 142.5(5) . . . . ?
C12 C17 C16 C15 0.3(8) . . . . ?
C12 C13 C14 C15 0.4(8) . . . . ?
C33 N3 C27 C28 -5.2(7) . . . . ?
C33 N3 C27 C32 177.1(5) . . . . ?
C33 N3 C26 C20 109.1(5) . . . . ?
C27 N3 C33 O4 177.9(4) . . . . ?
C27 N3 C33 C34 -5.5(7) . . . . ?
C27 N3 C26 C20 -73.4(6) . . . . ?
C27 C28 C29 C30 0.7(8) . . . . ?
C27 C32 C31 C30 2.1(9) . . . . ?
C20 C21 C22 C23 1.4(8) . . . . ?
C20 C25 C24 C23 -0.1(8) . . . . ?
C1 C6 C5 C4 1.3(8) . . . . ?
C1 C2 C3 C4 0.3(9) . . . . ?
C7 N1 C8 O1 -3.6(7) . . . . ?
C7 N1 C8 C9 172.3(4) . . . . ?
C7 N1 C13 C12 177.9(4) . . . . ?
C7 N1 C13 C14 0.8(7) . . . . ?
C7 C1 C6 C5 177.3(5) . . . . ?
C7 C1 C2 C3 -178.0(5) . . . . ?
C8 N1 C7 C1 106.5(5) . . . . ?
C8 N1 C13 C12 -2.7(7) . . . . ?
C8 N1 C13 C14 -179.8(5) . . . . ?
C8 C9 C10 O3 120.7(5) . . . . ?
C8 C9 C10 C11 -119.2(5) . . . . ?
C35 O5 C37 C38 -174.7(6) . . . . ?
C21 C20 C26 N3 165.5(5) . . . . ?
C21 C20 C25 C24 1.2(8) . . . . ?
C6 C1 C7 N1 158.6(4) . . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
C17 C12 C13 N1 -178.8(5) . . . . ?
C17 C12 C13 C14 -1.6(7) . . . . ?
C17 C16 C15 C14 -1.4(9) . . . . ?
C9 N2 C12 C17 -167.0(5) . . . . ?
C9 N2 C12 C13 14.8(7) . . . . ?
C9 N2 C11 O2 179.4(6) . . . . ?
C9 N2 C11 C10 -2.6(4) . . . . ?
C26 N3 C33 O4 -4.8(7) . . . . ?
C26 N3 C33 C34 171.9(4) . . . . ?
C26 N3 C27 C28 177.5(4) . . . . ?
C26 N3 C27 C32 -0.2(7) . . . . ?
C26 C20 C21 C22 177.4(5) . . . . ?
C26 C20 C25 C24 -178.0(5) . . . . ?
C13 N1 C7 C1 -74.1(6) . . . . ?
C13 N1 C8 O1 177.0(5) . . . . ?
C13 N1 C8 C9 -7.1(7) . . . . ?
C13 C12 C17 C16 1.2(8) . . . . ?
C13 C14 C15 C16 1.1(9) . . . . ?
C2 C1 C7 N1 -23.6(7) . . . . ?
C2 C1 C6 C5 -0.6(7) . . . . ?
C36 N4 C34 C33 125.0(5) . . . . ?
C36 N4 C34 C35 1.7(4) . . . . ?
C36 N4 C28 C27 -122.2(6) . . . . ?
C36 N4 C28 C29 56.9(8) . . . . ?
C36 C35 C34 N4 -1.5(4) . . . . ?
C36 C35 C34 C33 -118.9(5) . . . . ?
C34 N4 C36 O6 -180.0(6) . . . . ?
C34 N4 C36 C35 -1.7(4) . . . . ?
C34 N4 C28 C27 15.5(7) . . . . ?
C34 N4 C28 C29 -165.4(5) . . . . ?
C34 C35 C36 O6 179.7(7) . . . . ?
C34 C35 C36 N4 1.6(4) . . . . ?
C25 C20 C21 C22 -1.8(8) . . . . ?
C25 C20 C26 N3 -15.4(7) . . . . ?
C25 C24 C23 C22 -0.3(8) . . . . ?
C24 C23 C22 C21 -0.4(8) . . . . ?
C28 N4 C36 O6 -34.2(10) . . . . ?
C28 N4 C36 C35 144.2(5) . . . . ?
C28 N4 C34 C33 -25.4(7) . . . . ?
C28 N4 C34 C35 -148.7(5) . . . . ?
C28 C27 C32 C31 -0.7(8) . . . . ?
C11 N2 C12 C17 56.4(8) . . . . ?
C11 N2 C12 C13 -121.8(6) . . . . ?
C11 N2 C9 C8 125.5(5) . . . . ?
C11 N2 C9 C10 2.6(4) . . . . ?
C32 C27 C28 N4 178.3(4) . . . . ?
C32 C27 C28 C29 -0.7(7) . . . . ?
C32 C31 C30 C29 -2.1(9) . . . . ?
C31 C30 C29 C28 0.7(8) . . . . ?
C10 O3 C18 C19 178.5(6) . . . . ?
C5 C4 C3 C2 0.3(9) . . . . ?
C3 C4 C5 C6 -1.1(8) . . . . ?
C37 O5 C35 C36 82.2(6) . . . . ?
C37 O5 C35 C34 -178.4(5) . . . . ?
C18 O3 C10 C9 -179.7(5) . . . . ?
C18 O3 C10 C11 81.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.566
_oxdiff_exptl_absorpt_empirical_full_min 0.644
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.679(7)
2 0.321(7)

####################################################################### 
# 
# 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_ly
_database_code_depnum_ccdc_archive 'CCDC 2494770'
loop_
_audit_author_name
_audit_author_address
'Chongqing Pan'
;Anhui University
China
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
_audit_creation_date             2025-08-19
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O2'
_chemical_formula_sum            'C23 H21 N O2'
_chemical_formula_weight         343.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.5050(3)
_cell_length_b                   9.0705(2)
_cell_length_c                   13.1678(4)
_cell_angle_alpha                84.919(2)
_cell_angle_beta                 71.480(3)
_cell_angle_gamma                75.360(2)
_cell_volume                     931.91(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7129
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4610
_cell_measurement_theta_min      3.5210
_cell_oxdiff_angle_alpha         84.919(2)
_cell_oxdiff_angle_beta          71.480(3)
_cell_oxdiff_angle_gamma         75.360(2)
_cell_oxdiff_length_a            8.5050(3)
_cell_oxdiff_length_b            9.0705(2)
_cell_oxdiff_length_c            13.1678(4)
_cell_oxdiff_measurement_reflns_used 7117
_cell_oxdiff_volume              931.90(5)
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13882
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         3.540
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -34.00   0.50    0.20    -- -105.00  61.00  90.00   62
  2  ω    -23.00   5.00   0.50    0.10    --  -46.65  19.00  90.00   56
  3  ω    -20.00  24.00   0.50    0.10    --  -46.65  19.00  30.00   88
  4  ω    -71.00 -34.00   0.50    0.20    -- -105.00  61.00 -60.00   74
  5  ω    -21.00   5.00   0.50    0.10    --  -46.65  19.00-120.00   52
  6  ω    -10.00  27.00   0.50    0.10    --   46.65 -19.00   0.00   74
  7  ω    -29.00  22.00   0.50    0.10    --   46.65 -19.00-180.00  102
  8  ω    126.00 152.00   0.50    0.20    --  108.03  83.00 100.00   52
  9  ω    -22.00  43.00   0.50    0.10    --   46.65 -38.00 120.00  130
 10  ω     44.00  79.00   0.50    0.20    --  108.03-125.00  60.00   70
 11  ω     87.00 112.00   0.50    0.20    --  108.03-125.00  60.00   50
 12  ω     66.00  91.00   0.50    0.20    --  108.03-125.00   0.00   50
 13  ω     45.00  71.00   0.50    0.20    --  108.03 -95.00 -30.00   52
 14  ω     78.00 103.00   0.50    0.20    --  108.03 -95.00 -30.00   50
 15  ω     35.00  72.00   0.50    0.20    --  108.03 -83.00 -20.00   74
 16  ω     -6.00  73.00   0.50    0.10    --   46.65 -83.00 -20.00  158
 17  ω     50.00 111.00   0.50    0.20    --  108.03-125.00-150.00  122
 18  ω     81.00 107.00   0.50    0.20    --  108.03-125.00-180.00   52
 19  ω     35.00  80.00   0.50    0.20    --  108.03 -95.00-150.00   90
 20  ω     36.00  68.00   0.50    0.20    --  108.03 -61.00-180.00   64
 21  ω     78.00 104.00   0.50    0.20    --  108.03 -77.00-180.00   52
 22  ω     37.00  67.00   0.50    0.20    --  108.03 -61.00-120.00   60
 23  ω     39.00  71.00   0.50    0.20    --  108.03 -61.00  60.00   64
 24  ω     35.00  71.00   0.50    0.20    --  108.03 -61.00 120.00   72
 25  ω    140.00 172.00   0.50    0.20    --  108.03  45.00  90.00   64
 26  ω    105.00 176.00   0.50    0.20    --  108.03  61.00 120.00  142
 27  ω    116.00 176.00   0.50    0.20    --  108.03  45.00 150.00  120
 28  ω     95.00 134.00   0.50    0.20    --  108.03  45.00  90.00   78
 29  ω     99.00 173.00   0.50    0.20    --  108.03  77.00-120.00  148
 30  ω    110.00 176.00   0.50    0.20    --  108.03  61.00-180.00  132
 31  ω    -46.00  19.00   0.50    0.10    --  -46.65  83.00 100.00  130
 32  ω   -109.00 -35.00   0.50    0.20    -- -105.00 125.00  30.00  148
 33  ω    -96.00 -45.00   0.50    0.20    -- -105.00  83.00 100.00  102
 34  ω   -139.00 -92.00   0.50    0.20    -- -105.00 -30.00-120.00   94
 35  ω   -173.00-142.00   0.50    0.20    -- -105.00 -61.00-120.00   62
 36  ω   -130.00 -88.00   0.50    0.20    -- -105.00 -61.00-120.00   84
 37  ω   -119.00 -24.00   0.50    0.10    --  -46.65 -77.00 -60.00  190
 38  ω   -175.00 -89.00   0.50    0.20    -- -105.00 -30.00   0.00  172
 39  ω   -151.00-126.00   0.50    0.20    -- -105.00 -83.00 -20.00   50
 40  ω    -72.00 -46.00   0.50    0.10    --  -46.65 -38.00-150.00   52
 41  ω    -29.00  22.00   0.50    0.10    --   46.65 -19.00  60.00  102
 42  ω     94.00 119.00   0.50    0.10    --   46.65 178.00 -90.00   50
 43  ω     44.00  70.00   0.50    0.10    --   46.65 178.00 -90.00   52
 44  ω     93.00 119.00   0.50    0.10    --   46.65 178.00 120.00   52
 45  ω   -112.00 -60.00   0.50    0.20    -- -105.00 125.00  90.00  104
 46  ω   -114.00 -88.00   0.50    0.20    -- -105.00-125.00 150.00   52
 47  ω   -171.00-110.00   0.50    0.20    -- -105.00 -95.00 -90.00  122
 48  ω   -165.00-139.00   0.50    0.20    -- -105.00-125.00 150.00   52
 49  ω     79.00 105.00   0.50    0.20    --  108.03 -77.00 -60.00   52
 50  ω     43.00  69.00   0.50    0.20    --  108.03 -61.00  90.00   52
 51  ω     87.00 112.00   0.50    0.20    --  108.03-125.00 -30.00   50
 52  ω     44.00  70.00   0.50    0.20    --  108.03 -77.00 -60.00   52
 53  ω     86.00 112.00   0.50    0.20    --  108.03-125.00 120.00   52
 54  ω     86.00 112.00   0.50    0.20    --  108.03-125.00  30.00   52
 55  ω     79.00 105.00   0.50    0.20    --  108.03 -77.00 150.00   52
 56  ω     83.00 112.00   0.50    0.20    --  108.03-125.00 -60.00   58
 57  ω     35.00  62.00   0.50    0.20    --  108.03 -61.00 150.00   54
 58  ω     39.00  68.00   0.50    0.20    --  108.03-125.00 -30.00   58
 59  ω   -119.00 -23.00   0.50    0.10    --  -46.65 -77.00-180.00  192
 60  ω   -119.00 -67.00   0.50    0.10    --  -46.65 -77.00  60.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1019279000
_diffrn_orient_matrix_UB_12      0.0186923000
_diffrn_orient_matrix_UB_13      -0.0802650000
_diffrn_orient_matrix_UB_21      0.1413191000
_diffrn_orient_matrix_UB_22      -0.1239438000
_diffrn_orient_matrix_UB_23      -0.0710856000
_diffrn_orient_matrix_UB_31      -0.0912061000
_diffrn_orient_matrix_UB_32      -0.1229087000
_diffrn_orient_matrix_UB_33      0.0610702000
_diffrn_oxdiff_digest_hkl        
;
016097d18a11a7f7048bb13a4ea394d9c3ec57
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2572
_reflns_number_total             3281
_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       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.046
_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)+(0.0877P)²+0.2023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1643
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C19, N1
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0004
 C20, N1
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0004
 C22, C23
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0004
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C17(H17), C14(H14), C5(H5), C3(H3), C15(H15), C4(H4), C16(H16),
 C8(H8), C11(H11), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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 0.49741(19) 0.31977(17) 0.14835(12) 0.0533(4) Uani 1 1 d . U . . .
O1 O 0.27822(18) 0.45255(19) 0.09217(13) 0.0762(5) Uani 1 1 d . . . . .
O2 O 0.31766(19) 0.72989(18) 0.13292(13) 0.0786(5) Uani 1 1 d . . . . .
C18 C 0.5561(3) 0.0364(2) 0.16947(15) 0.0552(5) Uani 1 1 d . . . . .
C1 C 0.6338(2) 0.31753(19) 0.19121(16) 0.0527(5) Uani 1 1 d . . . . .
C6 C 0.6052(3) 0.2936(2) 0.30111(16) 0.0567(5) Uani 1 1 d . . . . .
C13 C 0.5116(2) 0.0126(2) 0.28038(15) 0.0543(5) Uani 1 1 d . . . . .
C20 C 0.3928(2) 0.4513(2) 0.12959(16) 0.0580(5) Uani 1 1 d . U . . .
C2 C 0.7876(3) 0.3422(2) 0.12467(19) 0.0621(5) Uani 1 1 d . . . . .
H2 H 0.805484 0.356150 0.051403 0.074 Uiso 1 1 calc R U . . .
C7 C 0.4392(3) 0.2650(2) 0.36950(15) 0.0612(5) Uani 1 1 d . . . . .
C19 C 0.4717(3) 0.1768(2) 0.12021(17) 0.0656(6) Uani 1 1 d . U . . .
H19A H 0.514450 0.166524 0.042937 0.079 Uiso 1 1 calc R U . . .
H19B H 0.350029 0.182887 0.141952 0.079 Uiso 1 1 calc R U . . .
C12 C 0.3926(3) 0.1317(2) 0.35715(15) 0.0593(5) Uani 1 1 d . . . . .
C17 C 0.6727(3) -0.0791(3) 0.10388(17) 0.0687(6) Uani 1 1 d . . . . .
H17 H 0.705463 -0.063637 0.030098 0.082 Uiso 1 1 calc R U . . .
C14 C 0.5819(3) -0.1270(2) 0.32041(18) 0.0672(6) Uani 1 1 d . . . . .
H14 H 0.551622 -0.144126 0.394024 0.081 Uiso 1 1 calc R U . . .
C5 C 0.7361(3) 0.2975(2) 0.3424(2) 0.0712(6) Uani 1 1 d . . . . .
H5 H 0.720447 0.282100 0.415359 0.085 Uiso 1 1 calc R U . . .
C21 C 0.4285(3) 0.5966(2) 0.1556(2) 0.0705(6) Uani 1 1 d . . . . .
H21A H 0.419143 0.595259 0.230992 0.085 Uiso 1 1 calc R U . . .
H21B H 0.544994 0.599169 0.114903 0.085 Uiso 1 1 calc R U . . .
C3 C 0.9145(3) 0.3457(2) 0.1684(2) 0.0738(7) Uani 1 1 d . . . . .
H3 H 1.018014 0.363043 0.124311 0.089 Uiso 1 1 calc R U . . .
C15 C 0.6957(3) -0.2402(3) 0.2527(2) 0.0791(7) Uani 1 1 d . . . . .
H15 H 0.741283 -0.333047 0.280635 0.095 Uiso 1 1 calc R U . . .
C4 C 0.8887(3) 0.3240(2) 0.2761(2) 0.0807(8) Uani 1 1 d . . . . .
H4 H 0.974563 0.327059 0.304793 0.097 Uiso 1 1 calc R U . . .
C16 C 0.7412(3) -0.2160(3) 0.1450(2) 0.0801(7) Uani 1 1 d . . . . .
H16 H 0.818551 -0.292060 0.099173 0.096 Uiso 1 1 calc R U . . .
C8 C 0.3281(4) 0.3701(3) 0.44681(19) 0.0817(7) Uani 1 1 d . . . . .
H8 H 0.359067 0.458142 0.456039 0.098 Uiso 1 1 calc R U . . .
C11 C 0.2362(3) 0.1085(3) 0.42240(18) 0.0814(7) Uani 1 1 d . . . . .
H11 H 0.204510 0.020038 0.415152 0.098 Uiso 1 1 calc R U . . .
C9 C 0.1724(4) 0.3452(4) 0.5100(2) 0.1007(10) Uani 1 1 d . . . . .
H9 H 0.098547 0.416799 0.560633 0.121 Uiso 1 1 calc R U . . .
C10 C 0.1274(4) 0.2148(5) 0.4978(2) 0.1016(10) Uani 1 1 d . . . . .
H10 H 0.023057 0.197672 0.540413 0.122 Uiso 1 1 calc R U . . .
C23 C 0.0709(4) 0.9265(3) 0.1968(3) 0.1101(10) Uani 1 1 d . U . . .
H23A H 0.055691 0.934020 0.127208 0.165 Uiso 1 1 calc R U . . .
H23B H 0.135721 0.996974 0.201281 0.165 Uiso 1 1 calc R U . . .
H23C H -0.038662 0.950272 0.250534 0.165 Uiso 1 1 calc R U . . .
C22 C 0.1652(4) 0.7662(3) 0.2149(3) 0.1038(9) Uani 1 1 d . U . . .
H22A H 0.187349 0.759410 0.283226 0.125 Uiso 1 1 calc R U . . .
H22B H 0.096428 0.695181 0.216051 0.125 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 C1 1.438(2) . ?
N1 C20 1.352(2) . ?
N1 C19 1.465(2) . ?
O1 C20 1.221(2) . ?
O2 C21 1.406(2) . ?
O2 C22 1.383(3) . ?
C18 C13 1.399(3) . ?
C18 C19 1.498(3) . ?
C18 C17 1.385(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.384(3) . ?
C6 C7 1.485(3) . ?
C6 C5 1.395(3) . ?
C13 C12 1.484(3) . ?
C13 C14 1.392(3) . ?
C20 C21 1.515(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C7 C12 1.402(3) . ?
C7 C8 1.394(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C12 C11 1.391(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.369(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(4) . ?
C4 H4 0.9300 . ?
C16 H16 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.384(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.369(5) . ?
C10 H10 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 C22 1.511(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
C1 N1 C19 120.08(15) . . ?
C20 N1 C1 122.08(15) . . ?
C20 N1 C19 117.81(15) . . ?
C22 O2 C21 112.06(19) . . ?
C13 C18 C19 122.03(19) . . ?
C17 C18 C13 118.32(19) . . ?
C17 C18 C19 119.47(18) . . ?
C6 C1 N1 118.33(17) . . ?
C2 C1 N1 120.25(17) . . ?
C2 C1 C6 121.40(17) . . ?
C1 C6 C7 119.72(16) . . ?
C5 C6 C1 117.8(2) . . ?
C5 C6 C7 122.47(19) . . ?
C18 C13 C12 122.21(17) . . ?
C14 C13 C18 119.06(19) . . ?
C14 C13 C12 118.73(18) . . ?
N1 C20 C21 116.05(15) . . ?
O1 C20 N1 121.77(19) . . ?
O1 C20 C21 122.17(18) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C12 C7 C6 120.29(17) . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 C12 119.2(2) . . ?
N1 C19 C18 114.94(15) . . ?
N1 C19 H19A 108.5 . . ?
N1 C19 H19B 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C7 C12 C13 120.90(18) . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 C7 118.8(2) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.1 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
O2 C21 C20 113.62(17) . . ?
O2 C21 H21A 108.8 . . ?
O2 C21 H21B 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.49(19) . . ?
C3 C4 H4 119.8 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
O2 C22 C23 108.8(2) . . ?
O2 C22 H22A 109.9 . . ?
O2 C22 H22B 109.9 . . ?
C23 C22 H22A 109.9 . . ?
C23 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?

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 C6 C7 2.5(2) . . . . ?
N1 C1 C6 C5 -177.57(16) . . . . ?
N1 C1 C2 C3 177.35(17) . . . . ?
N1 C20 C21 O2 179.04(17) . . . . ?
O1 C20 C21 O2 0.3(3) . . . . ?
C18 C13 C12 C7 -68.1(2) . . . . ?
C18 C13 C12 C11 115.5(2) . . . . ?
C18 C13 C14 C15 0.9(3) . . . . ?
C18 C17 C16 C15 -0.5(3) . . . . ?
C1 N1 C20 O1 179.24(18) . . . . ?
C1 N1 C20 C21 0.5(3) . . . . ?
C1 N1 C19 C18 18.1(3) . . . . ?
C1 C6 C7 C12 66.3(2) . . . . ?
C1 C6 C7 C8 -113.9(2) . . . . ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C7 C12 C13 3.6(3) . . . . ?
C6 C7 C12 C11 -179.94(18) . . . . ?
C6 C7 C8 C9 179.3(2) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C13 C18 C19 N1 62.9(2) . . . . ?
C13 C18 C17 C16 1.6(3) . . . . ?
C13 C12 C11 C10 176.9(2) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C20 N1 C1 C6 97.4(2) . . . . ?
C20 N1 C1 C2 -81.1(2) . . . . ?
C20 N1 C19 C18 -163.86(18) . . . . ?
C2 C1 C6 C7 -179.01(17) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C7 C6 C5 C4 179.83(18) . . . . ?
C7 C12 C11 C10 0.4(3) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C19 N1 C1 C6 -84.6(2) . . . . ?
C19 N1 C1 C2 96.8(2) . . . . ?
C19 N1 C20 O1 1.2(3) . . . . ?
C19 N1 C20 C21 -177.55(18) . . . . ?
C19 C18 C13 C12 -7.2(3) . . . . ?
C19 C18 C13 C14 173.30(17) . . . . ?
C19 C18 C17 C16 -173.58(18) . . . . ?
C12 C13 C14 C15 -178.6(2) . . . . ?
C12 C7 C8 C9 -0.9(3) . . . . ?
C12 C11 C10 C9 -0.4(4) . . . . ?
C17 C18 C13 C12 177.75(17) . . . . ?
C17 C18 C13 C14 -1.7(3) . . . . ?
C17 C18 C19 N1 -122.1(2) . . . . ?
C14 C13 C12 C7 111.4(2) . . . . ?
C14 C13 C12 C11 -65.0(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C5 C6 C7 C12 -113.7(2) . . . . ?
C5 C6 C7 C8 66.2(3) . . . . ?
C21 O2 C22 C23 167.3(2) . . . . ?
C8 C7 C12 C13 -176.28(18) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C22 O2 C21 C20 83.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.949
_oxdiff_exptl_absorpt_empirical_full_min 0.666
