# Supplementary Information (SI) for Green Chemistry.
# 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_k11009-jjw-i(tpg-75)
_database_code_depnum_ccdc_archive 'CCDC 2226537'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University Taiwan
Taiwan
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2025-12-26 downloaded from the CCDC.
;
_audit_creation_date             2021-09-23
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 N2 O'
_chemical_formula_sum            'C25 H20 N2 O'
_chemical_formula_weight         364.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H21 O N'
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      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                   10.5120(2)
_cell_length_b                   11.1768(2)
_cell_length_c                   15.6769(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.894(2)
_cell_angle_gamma                90
_cell_volume                     1839.54(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24351
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9250
_cell_measurement_theta_min      1.9270
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39748
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.940
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  38.00   0.50   18.34    --   10.60 -82.00 -60.00  234
  2  ω    -79.00  41.00   0.50   18.34    --   10.60 -57.00-180.00  240
  3  ω    -17.00 100.00   0.50   18.34    --   10.60  82.00 -30.00  234
  4  ω    -79.00  36.00   0.50   18.34    --   10.60 -77.00-120.00  230
  5  ω    -15.00 100.00   0.50   18.34    --   10.60  77.00  60.00  230
  6  ω    -17.00 100.00   0.50   18.34    --   10.60  82.00 -60.00  234
  7  ω   -100.00  15.00   0.50   18.34    --  -10.90 -77.00 120.00  230
  8  ω    -79.00  36.00   0.50   18.34    --   10.60 -77.00 120.00  230
  9  ω    -79.00  36.00   0.50   18.34    --   10.60 -77.00   0.00  230
 10  ω    -15.00 100.00   0.50   18.34    --   10.60  77.00-150.00  230
 11  ω    -79.00  15.00   0.50   18.34    --   10.60 -82.00-180.00  188
 12  ω    -79.00  36.00   0.50   18.34    --   10.60 -77.00  60.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032269000
_diffrn_orient_matrix_UB_12      0.0261386000
_diffrn_orient_matrix_UB_13      -0.0412753000
_diffrn_orient_matrix_UB_21      -0.0107517000
_diffrn_orient_matrix_UB_22      0.0568396000
_diffrn_orient_matrix_UB_23      0.0183928000
_diffrn_orient_matrix_UB_31      0.0666549000
_diffrn_orient_matrix_UB_32      0.0104361000
_diffrn_orient_matrix_UB_33      0.0032717000
_diffrn_oxdiff_digest_frames     
;
0113726419dadcd2a079d127e44d191712000251777
;
_diffrn_oxdiff_digest_hkl        
;
01c40d114e020224ad194756832b075f27569f
;
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2900
_reflns_number_total             3243
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     960
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+0.6723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim N1 \\sim N2 \\sim O1: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C17(H17)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
3.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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
O1 O 1.09156(8) 0.42973(8) 0.16967(6) 0.0269(2) Uani 1 1 d . U . . .
N1 N 0.96569(10) 0.57469(9) 0.10368(6) 0.0207(2) Uani 1 1 d . U . . .
N2 N 0.86264(11) 0.21169(10) 0.20258(7) 0.0267(3) Uani 1 1 d . U . . .
C1 C 0.98955(12) 0.47950(11) 0.15424(7) 0.0205(3) Uani 1 1 d . U . . .
C2 C 0.86141(11) 0.44441(10) 0.19146(7) 0.0178(3) Uani 1 1 d . U . . .
C3 C 0.76379(11) 0.49565(10) 0.12288(7) 0.0178(3) Uani 1 1 d . U . . .
H3 H 0.759293 0.444166 0.070651 0.021 Uiso 1 1 calc R . . . .
C4 C 0.83274(11) 0.61646(11) 0.10531(7) 0.0190(3) Uani 1 1 d . U . . .
C5 C 0.78746(12) 0.66783(11) 0.02075(8) 0.0238(3) Uani 1 1 d . U . . .
H5 H 0.808776 0.627705 -0.030004 0.029 Uiso 1 1 calc R . . . .
C6 C 0.71876(13) 0.76724(12) 0.01427(8) 0.0274(3) Uani 1 1 d . U . . .
H6 H 0.687466 0.792803 -0.040649 0.033 Uiso 1 1 calc R . . . .
C7 C 0.68963(13) 0.83872(12) 0.08883(8) 0.0271(3) Uani 1 1 d . U . . .
H7 H 0.635978 0.906798 0.081972 0.033 Uiso 1 1 calc R . . . .
C8 C 0.73727(12) 0.80961(11) 0.16594(8) 0.0241(3) Uani 1 1 d . U . . .
H8 H 0.718760 0.859870 0.212584 0.029 Uiso 1 1 calc R . . . .
C9 C 0.81889(12) 0.70140(10) 0.18336(7) 0.0194(3) Uani 1 1 d . U . . .
H9 H 0.905975 0.729594 0.202556 0.023 Uiso 1 1 calc R . . . .
C10 C 0.76446(12) 0.62786(10) 0.25749(7) 0.0188(3) Uani 1 1 d . U . . .
H10 H 0.759855 0.678978 0.309589 0.023 Uiso 1 1 calc R . . . .
C11 C 0.63372(12) 0.58685(10) 0.22826(7) 0.0186(3) Uani 1 1 d . U . . .
C12 C 0.51995(12) 0.61180(11) 0.26555(8) 0.0229(3) Uani 1 1 d . U . . .
H12 H 0.519108 0.661740 0.314556 0.027 Uiso 1 1 calc R . . . .
C13 C 0.40715(13) 0.56337(12) 0.23088(9) 0.0263(3) Uani 1 1 d . U . . .
H13 H 0.328993 0.579959 0.256398 0.032 Uiso 1 1 calc R . . . .
C14 C 0.40827(12) 0.49081(12) 0.15908(8) 0.0264(3) Uani 1 1 d . U . . .
H14 H 0.330798 0.457552 0.136012 0.032 Uiso 1 1 calc R . . . .
C15 C 0.52145(12) 0.46638(11) 0.12065(8) 0.0217(3) Uani 1 1 d . U . . .
H15 H 0.521781 0.417336 0.071170 0.026 Uiso 1 1 calc R . . . .
C16 C 0.63429(12) 0.51462(10) 0.15551(7) 0.0182(3) Uani 1 1 d . U . . .
C17 C 0.84865(12) 0.51540(10) 0.27789(7) 0.0184(3) Uani 1 1 d . U . . .
H17 H 0.935603 0.544530 0.296554 0.022 Uiso 1 1 calc R . . . .
C18 C 0.79707(11) 0.44642(10) 0.35200(7) 0.0189(3) Uani 1 1 d . U . . .
C19 C 0.85190(13) 0.46808(11) 0.43345(8) 0.0228(3) Uani 1 1 d . U . . .
H19 H 0.922333 0.521116 0.440027 0.027 Uiso 1 1 calc R . . . .
C20 C 0.80532(13) 0.41350(12) 0.50504(8) 0.0265(3) Uani 1 1 d . U . . .
H20 H 0.843615 0.429456 0.560048 0.032 Uiso 1 1 calc R . . . .
C21 C 0.70313(13) 0.33590(12) 0.49615(8) 0.0267(3) Uani 1 1 d . U . . .
H21 H 0.671262 0.298229 0.545028 0.032 Uiso 1 1 calc R . . . .
C22 C 0.64727(13) 0.31314(11) 0.41593(8) 0.0247(3) Uani 1 1 d . U . . .
H22 H 0.577135 0.259699 0.409762 0.030 Uiso 1 1 calc R . . . .
C23 C 0.69367(12) 0.36835(11) 0.34444(8) 0.0212(3) Uani 1 1 d . U . . .
H23 H 0.654416 0.352692 0.289661 0.025 Uiso 1 1 calc R . . . .
C24 C 0.85861(11) 0.31395(11) 0.19972(7) 0.0200(3) Uani 1 1 d . U . . .
C25 C 1.06585(13) 0.64955(12) 0.07162(8) 0.0270(3) Uani 1 1 d . U . . .
H25A H 1.065249 0.727588 0.100096 0.040 Uiso 1 1 calc GR . . . .
H25B H 1.051198 0.660590 0.009895 0.040 Uiso 1 1 calc GR . . . .
H25C H 1.148590 0.610907 0.083280 0.040 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2214(15) . ?
N1 C1 1.3428(16) . ?
N1 C4 1.4750(16) . ?
N1 C25 1.4540(16) . ?
N2 C24 1.1445(16) . ?
C1 C2 1.5454(17) . ?
C2 C3 1.5574(16) . ?
C2 C17 1.5816(15) . ?
C2 C24 1.4644(17) . ?
C3 H3 1.0000 . ?
C3 C4 1.5635(16) . ?
C3 C16 1.4933(17) . ?
C4 C5 1.4999(17) . ?
C4 C9 1.5612(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3263(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.4609(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.3255(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.4999(17) . ?
C9 H9 1.0000 . ?
C9 C10 1.5558(16) . ?
C10 H10 1.0000 . ?
C10 C11 1.4985(17) . ?
C10 C17 1.5610(16) . ?
C11 C12 1.3858(17) . ?
C11 C16 1.3976(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3890(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3879(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3875(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3895(17) . ?
C17 H17 1.0000 . ?
C17 C18 1.5172(16) . ?
C18 C19 1.3954(17) . ?
C18 C23 1.3942(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3881(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.3843(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.3892(17) . ?
C23 H23 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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 C4 112.92(10) . . ?
C1 N1 C25 122.89(11) . . ?
C25 N1 C4 121.81(10) . . ?
O1 C1 N1 127.86(12) . . ?
O1 C1 C2 125.66(11) . . ?
N1 C1 C2 106.47(10) . . ?
C1 C2 C3 101.68(9) . . ?
C1 C2 C17 108.02(9) . . ?
C3 C2 C17 109.00(9) . . ?
C24 C2 C1 107.93(10) . . ?
C24 C2 C3 114.31(10) . . ?
C24 C2 C17 114.89(10) . . ?
C2 C3 H3 110.8 . . ?
C2 C3 C4 98.28(9) . . ?
C4 C3 H3 110.8 . . ?
C16 C3 C2 113.33(9) . . ?
C16 C3 H3 110.8 . . ?
C16 C3 C4 112.12(10) . . ?
N1 C4 C3 100.24(9) . . ?
N1 C4 C5 111.37(10) . . ?
N1 C4 C9 109.39(10) . . ?
C5 C4 C3 110.92(10) . . ?
C5 C4 C9 114.95(10) . . ?
C9 C4 C3 108.95(9) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.39(11) . . ?
C6 C5 H5 118.8 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.15(12) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.71(12) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 118.3 . . ?
C7 C8 C9 123.39(12) . . ?
C9 C8 H8 118.3 . . ?
C4 C9 H9 107.9 . . ?
C8 C9 C4 115.01(10) . . ?
C8 C9 H9 107.9 . . ?
C8 C9 C10 109.48(10) . . ?
C10 C9 C4 108.45(9) . . ?
C10 C9 H9 107.9 . . ?
C9 C10 H10 110.1 . . ?
C9 C10 C17 110.64(9) . . ?
C11 C10 C9 107.42(9) . . ?
C11 C10 H10 110.1 . . ?
C11 C10 C17 108.55(9) . . ?
C17 C10 H10 110.1 . . ?
C12 C11 C10 127.39(11) . . ?
C12 C11 C16 119.99(11) . . ?
C16 C11 C10 112.62(10) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.63(12) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.20(12) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.65(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.11(12) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C3 113.77(10) . . ?
C15 C16 C3 125.81(11) . . ?
C15 C16 C11 120.42(11) . . ?
C2 C17 H17 107.3 . . ?
C10 C17 C2 107.46(9) . . ?
C10 C17 H17 107.3 . . ?
C18 C17 C2 116.75(10) . . ?
C18 C17 C10 110.20(9) . . ?
C18 C17 H17 107.3 . . ?
C19 C18 C17 117.74(11) . . ?
C23 C18 C17 124.07(11) . . ?
C23 C18 C19 118.08(11) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.15(12) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.89(12) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.91(12) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.08(12) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.88(12) . . ?
C22 C23 H23 119.6 . . ?
N2 C24 C2 175.57(13) . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O1 C1 C2 C3 -156.10(12) . . . . ?
O1 C1 C2 C17 89.26(14) . . . . ?
O1 C1 C2 C24 -35.52(16) . . . . ?
N1 C1 C2 C3 24.69(11) . . . . ?
N1 C1 C2 C17 -89.94(11) . . . . ?
N1 C1 C2 C24 145.28(10) . . . . ?
N1 C4 C5 C6 -137.68(12) . . . . ?
N1 C4 C9 C8 139.04(10) . . . . ?
N1 C4 C9 C10 -98.05(11) . . . . ?
C1 N1 C4 C3 -30.24(12) . . . . ?
C1 N1 C4 C5 -147.65(10) . . . . ?
C1 N1 C4 C9 84.18(12) . . . . ?
C1 C2 C3 C4 -40.63(10) . . . . ?
C1 C2 C3 C16 -159.12(10) . . . . ?
C1 C2 C17 C10 97.69(11) . . . . ?
C1 C2 C17 C18 -137.99(10) . . . . ?
C2 C3 C4 N1 42.16(10) . . . . ?
C2 C3 C4 C5 159.90(10) . . . . ?
C2 C3 C4 C9 -72.60(11) . . . . ?
C2 C3 C16 C11 55.11(13) . . . . ?
C2 C3 C16 C15 -124.03(12) . . . . ?
C2 C17 C18 C19 140.80(11) . . . . ?
C2 C17 C18 C23 -43.17(16) . . . . ?
C3 C2 C17 C10 -12.02(12) . . . . ?
C3 C2 C17 C18 112.30(11) . . . . ?
C3 C4 C5 C6 111.59(13) . . . . ?
C3 C4 C9 C8 -112.29(11) . . . . ?
C3 C4 C9 C10 10.63(13) . . . . ?
C4 N1 C1 O1 -175.52(11) . . . . ?
C4 N1 C1 C2 3.66(13) . . . . ?
C4 C3 C16 C11 -55.05(13) . . . . ?
C4 C3 C16 C15 125.81(12) . . . . ?
C4 C5 C6 C7 4.4(2) . . . . ?
C4 C9 C10 C11 -63.77(12) . . . . ?
C4 C9 C10 C17 54.55(12) . . . . ?
C5 C4 C9 C8 12.89(15) . . . . ?
C5 C4 C9 C10 135.81(11) . . . . ?
C5 C6 C7 C8 3.7(2) . . . . ?
C6 C7 C8 C9 -2.3(2) . . . . ?
C7 C8 C9 C4 -6.24(18) . . . . ?
C7 C8 C9 C10 -128.61(13) . . . . ?
C8 C9 C10 C11 62.43(12) . . . . ?
C8 C9 C10 C17 -179.24(10) . . . . ?
C9 C4 C5 C6 -12.56(17) . . . . ?
C9 C10 C11 C12 -120.50(13) . . . . ?
C9 C10 C11 C16 60.30(12) . . . . ?
C9 C10 C17 C2 -53.51(12) . . . . ?
C9 C10 C17 C18 178.28(9) . . . . ?
C10 C11 C12 C13 -178.30(11) . . . . ?
C10 C11 C16 C3 -0.61(14) . . . . ?
C10 C11 C16 C15 178.58(10) . . . . ?
C10 C17 C18 C19 -96.28(13) . . . . ?
C10 C17 C18 C23 79.75(14) . . . . ?
C11 C10 C17 C2 64.12(11) . . . . ?
C11 C10 C17 C18 -64.08(12) . . . . ?
C11 C12 C13 C14 -0.28(18) . . . . ?
C12 C11 C16 C3 -179.88(10) . . . . ?
C12 C11 C16 C15 -0.69(17) . . . . ?
C12 C13 C14 C15 -0.47(19) . . . . ?
C13 C14 C15 C16 0.63(18) . . . . ?
C14 C15 C16 C3 179.03(11) . . . . ?
C14 C15 C16 C11 -0.05(17) . . . . ?
C16 C3 C4 N1 161.57(9) . . . . ?
C16 C3 C4 C5 -80.68(12) . . . . ?
C16 C3 C4 C9 46.82(13) . . . . ?
C16 C11 C12 C13 0.85(18) . . . . ?
C17 C2 C3 C4 73.29(10) . . . . ?
C17 C2 C3 C16 -45.21(13) . . . . ?
C17 C10 C11 C12 119.84(13) . . . . ?
C17 C10 C11 C16 -59.36(12) . . . . ?
C17 C18 C19 C20 176.39(11) . . . . ?
C17 C18 C23 C22 -176.46(11) . . . . ?
C18 C19 C20 C21 0.20(19) . . . . ?
C19 C18 C23 C22 -0.45(18) . . . . ?
C19 C20 C21 C22 -0.21(19) . . . . ?
C20 C21 C22 C23 -0.11(19) . . . . ?
C21 C22 C23 C18 0.45(19) . . . . ?
C23 C18 C19 C20 0.13(18) . . . . ?
C24 C2 C3 C4 -156.63(10) . . . . ?
C24 C2 C3 C16 84.87(13) . . . . ?
C24 C2 C17 C10 -141.79(11) . . . . ?
C24 C2 C17 C18 -17.47(15) . . . . ?
C25 N1 C1 O1 -12.79(19) . . . . ?
C25 N1 C1 C2 166.39(10) . . . . ?
C25 N1 C4 C3 166.82(10) . . . . ?
C25 N1 C4 C5 49.42(14) . . . . ?
C25 N1 C4 C9 -78.76(13) . . . . ?

_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 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_k11107-jjw-d(tpg82)_auto
_database_code_depnum_ccdc_archive 'CCDC 2226538'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University Taiwan
Taiwan
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2025-12-26 downloaded from the CCDC.
;
_audit_creation_date             2022-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 N2 O'
_chemical_formula_sum            'C26 H22 N2 O'
_chemical_formula_weight         378.45
_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      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                   10.3638(3)
_cell_length_b                   11.3229(3)
_cell_length_c                   16.6651(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.655(3)
_cell_angle_gamma                90
_cell_volume                     1951.64(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12610
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8590
_cell_measurement_theta_min      1.9660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22553
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00 100.00   0.50   15.49    --   10.60  82.00 -60.00  234
  2  ω    -79.00  41.00   0.50   15.49    --   10.60 -57.00  30.00  240
  3  ω    -15.00 100.00   0.50   15.49    --   10.60  77.00 -30.00  230
  4  ω   -100.00  17.00   0.50   15.49    --  -10.90 -82.00  90.00  234
  5  ω    -36.00  79.00   0.50   15.49    --  -10.90  77.00-150.00  230
  6  ω    -36.00  79.00   0.50   15.49    --  -10.90  77.00 -90.00  230
  7  ω    -79.00  36.00   0.50   15.49    --   10.60 -77.00 120.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088742000
_diffrn_orient_matrix_UB_12      0.0136355000
_diffrn_orient_matrix_UB_13      -0.0408409000
_diffrn_orient_matrix_UB_21      -0.0179982000
_diffrn_orient_matrix_UB_22      0.0593746000
_diffrn_orient_matrix_UB_23      0.0068707000
_diffrn_orient_matrix_UB_31      0.0655755000
_diffrn_orient_matrix_UB_32      0.0145011000
_diffrn_orient_matrix_UB_33      0.0102468000
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2759
_reflns_number_total             3383
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0073(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     984
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      0.988
_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)+(0.0604P)²+0.4471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim N1 \\sim N2 \\sim O1: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
3.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C13(H13), C20(H20)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_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
O1 O 0.39720(11) 0.56584(10) 0.83790(7) 0.0317(3) Uani 1 1 d . U . . .
N1 N 0.52224(13) 0.42046(12) 0.90050(8) 0.0254(3) Uani 1 1 d . U . . .
N2 N 0.63458(14) 0.77542(13) 0.80590(9) 0.0340(4) Uani 1 1 d . U . . .
C1 C 0.49967(16) 0.51457(14) 0.85276(10) 0.0249(4) Uani 1 1 d . U . . .
C2 C 0.62930(15) 0.54601(14) 0.81718(10) 0.0219(4) Uani 1 1 d . U . . .
C3 C 0.72897(15) 0.49219(13) 0.88078(10) 0.0217(4) Uani 1 1 d . U . . .
H3 H 0.737735 0.541900 0.928959 0.026 Uiso 1 1 calc R U . . .
C4 C 0.65569(15) 0.37532(14) 0.89811(10) 0.0238(4) Uani 1 1 d . U . . .
C5 C 0.63643(15) 0.47639(14) 0.73543(10) 0.0227(4) Uani 1 1 d . U . . .
H5 H 0.548322 0.452412 0.717712 0.027 Uiso 1 1 calc R U . . .
C6 C 0.69259(15) 0.54228(14) 0.66668(10) 0.0236(4) Uani 1 1 d . U . . .
C7 C 0.63950(17) 0.52332(14) 0.58888(10) 0.0270(4) Uani 1 1 d . U . . .
H7 H 0.564353 0.478801 0.580962 0.032 Uiso 1 1 calc R U . . .
C8 C 0.69746(17) 0.57015(15) 0.52275(11) 0.0296(4) Uani 1 1 d . U . . .
H8 H 0.660306 0.556597 0.471298 0.035 Uiso 1 1 calc R U . . .
C9 C 0.80975(16) 0.63669(14) 0.53248(10) 0.0274(4) Uani 1 1 d . U . . .
C10 C 0.85998(16) 0.65899(14) 0.60991(10) 0.0273(4) Uani 1 1 d . U . . .
H10 H 0.933556 0.705658 0.617694 0.033 Uiso 1 1 calc R U . . .
C11 C 0.80292(16) 0.61324(14) 0.67596(10) 0.0255(4) Uani 1 1 d . U . . .
H11 H 0.838497 0.629941 0.727350 0.031 Uiso 1 1 calc R U . . .
C12 C 0.8776(2) 0.68099(18) 0.46122(11) 0.0419(5) Uani 1 1 d . U . . .
H12A H 0.921862 0.753329 0.475182 0.063 Uiso 1 1 calc R U . . .
H12B H 0.815317 0.694870 0.417116 0.063 Uiso 1 1 calc R U . . .
H12C H 0.939041 0.623029 0.445903 0.063 Uiso 1 1 calc R U . . .
C13 C 0.71711(15) 0.36138(13) 0.75391(10) 0.0232(4) Uani 1 1 d . U . . .
H13 H 0.717265 0.311785 0.705720 0.028 Uiso 1 1 calc R U . . .
C14 C 0.85275(15) 0.39783(14) 0.77996(10) 0.0231(4) Uani 1 1 d . U . . .
C15 C 0.96447(16) 0.37213(15) 0.74217(11) 0.0284(4) Uani 1 1 d . U . . .
H15 H 0.961310 0.323522 0.697105 0.034 Uiso 1 1 calc R U . . .
C16 C 1.08152(17) 0.41965(15) 0.77218(12) 0.0325(4) Uani 1 1 d . U . . .
H16 H 1.156801 0.403517 0.746684 0.039 Uiso 1 1 calc R U . . .
C17 C 1.08650(16) 0.49075(15) 0.83972(12) 0.0307(4) Uani 1 1 d . U . . .
H17 H 1.165075 0.522816 0.859012 0.037 Uiso 1 1 calc R U . . .
C18 C 0.97575(15) 0.51464(14) 0.87886(11) 0.0263(4) Uani 1 1 d . U . . .
H18 H 0.979868 0.560892 0.925067 0.032 Uiso 1 1 calc R U . . .
C19 C 0.85849(15) 0.46894(13) 0.84852(10) 0.0220(4) Uani 1 1 d . U . . .
C20 C 0.66354(16) 0.29066(14) 0.82443(10) 0.0243(4) Uani 1 1 d . U . . .
H20 H 0.575391 0.265560 0.807738 0.029 Uiso 1 1 calc R U . . .
C21 C 0.74347(17) 0.18174(14) 0.84047(11) 0.0297(4) Uani 1 1 d . U . . .
H21 H 0.759271 0.132619 0.797463 0.036 Uiso 1 1 calc R U . . .
C22 C 0.79263(17) 0.15225(15) 0.91309(11) 0.0333(4) Uani 1 1 d . U . . .
H22 H 0.844235 0.085260 0.919230 0.040 Uiso 1 1 calc R U . . .
C23 C 0.76724(17) 0.22301(15) 0.98366(11) 0.0318(4) Uani 1 1 d . U . . .
H23 H 0.797422 0.196602 1.034264 0.038 Uiso 1 1 calc R U . . .
C24 C 0.70221(16) 0.32406(14) 0.97753(10) 0.0274(4) Uani 1 1 d . U . . .
H24 H 0.684975 0.364387 1.024274 0.033 Uiso 1 1 calc R U . . .
C25 C 0.41909(17) 0.34777(16) 0.92930(11) 0.0322(4) Uani 1 1 d . U . . .
H25A H 0.338761 0.390029 0.923154 0.048 Uiso 1 1 calc R U . . .
H25B H 0.437971 0.329368 0.985046 0.048 Uiso 1 1 calc R U . . .
H25C H 0.412455 0.275946 0.898706 0.048 Uiso 1 1 calc R U . . .
C26 C 0.63526(15) 0.67478(14) 0.80939(10) 0.0241(4) Uani 1 1 d . 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
O1 C1 1.2217(19) . ?
N1 C1 1.341(2) . ?
N1 C4 1.477(2) . ?
N1 C25 1.455(2) . ?
N2 C26 1.141(2) . ?
C1 C2 1.544(2) . ?
C2 C3 1.556(2) . ?
C2 C5 1.580(2) . ?
C2 C26 1.465(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.562(2) . ?
C3 C19 1.501(2) . ?
C4 C20 1.564(2) . ?
C4 C24 1.497(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.514(2) . ?
C5 C13 1.567(2) . ?
C6 C7 1.392(2) . ?
C6 C11 1.398(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(2) . ?
C9 C10 1.384(2) . ?
C9 C12 1.504(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9800 . ?
C13 C14 1.502(2) . ?
C13 C20 1.554(2) . ?
C14 C15 1.384(2) . ?
C14 C19 1.396(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(2) . ?
C20 H20 0.9800 . ?
C20 C21 1.500(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.326(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.461(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.328(2) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C1 N1 C4 112.77(13) . . ?
C1 N1 C25 122.76(14) . . ?
C25 N1 C4 121.47(13) . . ?
O1 C1 N1 127.90(16) . . ?
O1 C1 C2 125.37(15) . . ?
N1 C1 C2 106.72(13) . . ?
C1 C2 C3 101.78(13) . . ?
C1 C2 C5 107.81(12) . . ?
C3 C2 C5 109.05(12) . . ?
C26 C2 C1 107.82(13) . . ?
C26 C2 C3 114.83(13) . . ?
C26 C2 C5 114.55(13) . . ?
C2 C3 H3 110.8 . . ?
C2 C3 C4 98.52(12) . . ?
C4 C3 H3 110.8 . . ?
C19 C3 C2 113.25(13) . . ?
C19 C3 H3 110.8 . . ?
C19 C3 C4 111.97(13) . . ?
N1 C4 C3 100.31(12) . . ?
N1 C4 C20 109.20(13) . . ?
N1 C4 C24 111.08(14) . . ?
C3 C4 C20 108.90(13) . . ?
C24 C4 C3 111.04(13) . . ?
C24 C4 C20 115.26(13) . . ?
C2 C5 H5 107.7 . . ?
C6 C5 C2 116.62(13) . . ?
C6 C5 H5 107.7 . . ?
C6 C5 C13 109.39(13) . . ?
C13 C5 C2 107.39(12) . . ?
C13 C5 H5 107.7 . . ?
C7 C6 C5 118.71(14) . . ?
C7 C6 C11 117.61(16) . . ?
C11 C6 C5 123.41(15) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.87(15) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.00(16) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C12 121.33(16) . . ?
C10 C9 C8 118.11(16) . . ?
C10 C9 C12 120.55(16) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.29(16) . . ?
C11 C10 H10 119.4 . . ?
C6 C11 H11 119.5 . . ?
C10 C11 C6 121.03(16) . . ?
C10 C11 H11 119.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13 110.1 . . ?
C14 C13 C5 107.83(12) . . ?
C14 C13 H13 110.1 . . ?
C14 C13 C20 107.21(13) . . ?
C20 C13 C5 111.40(13) . . ?
C20 C13 H13 110.1 . . ?
C15 C14 C13 127.25(15) . . ?
C15 C14 C19 120.03(15) . . ?
C19 C14 C13 112.66(14) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.41(17) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.31(17) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.60(16) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.32(17) . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C3 113.70(14) . . ?
C18 C19 C3 125.96(15) . . ?
C18 C19 C14 120.30(16) . . ?
C4 C20 H20 107.8 . . ?
C13 C20 C4 108.48(12) . . ?
C13 C20 H20 107.8 . . ?
C21 C20 C4 114.82(14) . . ?
C21 C20 C13 109.80(13) . . ?
C21 C20 H20 107.8 . . ?
C20 C21 H21 118.5 . . ?
C22 C21 C20 123.06(16) . . ?
C22 C21 H21 118.5 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.22(16) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.81(17) . . ?
C24 C23 H23 119.1 . . ?
C4 C24 H24 118.8 . . ?
C23 C24 C4 122.35(16) . . ?
C23 C24 H24 118.8 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 C2 176.37(19) . . ?

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
O1 C1 C2 C3 157.33(16) . . . . ?
O1 C1 C2 C5 -88.01(18) . . . . ?
O1 C1 C2 C26 36.2(2) . . . . ?
N1 C1 C2 C3 -23.96(16) . . . . ?
N1 C1 C2 C5 90.70(15) . . . . ?
N1 C1 C2 C26 -145.14(13) . . . . ?
N1 C4 C20 C13 97.58(15) . . . . ?
N1 C4 C20 C21 -139.19(14) . . . . ?
N1 C4 C24 C23 136.80(16) . . . . ?
C1 N1 C4 C3 30.27(17) . . . . ?
C1 N1 C4 C20 -84.06(16) . . . . ?
C1 N1 C4 C24 147.74(14) . . . . ?
C1 C2 C3 C4 39.99(14) . . . . ?
C1 C2 C3 C19 158.43(13) . . . . ?
C1 C2 C5 C6 140.08(14) . . . . ?
C1 C2 C5 C13 -96.82(14) . . . . ?
C2 C3 C4 N1 -41.79(14) . . . . ?
C2 C3 C4 C20 72.77(15) . . . . ?
C2 C3 C4 C24 -159.28(13) . . . . ?
C2 C3 C19 C14 -55.05(17) . . . . ?
C2 C3 C19 C18 122.43(17) . . . . ?
C2 C5 C6 C7 -143.12(15) . . . . ?
C2 C5 C6 C11 43.0(2) . . . . ?
C2 C5 C13 C14 -65.04(16) . . . . ?
C2 C5 C13 C20 52.34(16) . . . . ?
C3 C2 C5 C6 -110.18(15) . . . . ?
C3 C2 C5 C13 12.92(16) . . . . ?
C3 C4 C20 C13 -11.06(17) . . . . ?
C3 C4 C20 C21 112.17(15) . . . . ?
C3 C4 C24 C23 -112.48(18) . . . . ?
C4 N1 C1 O1 174.53(16) . . . . ?
C4 N1 C1 C2 -4.14(17) . . . . ?
C4 C3 C19 C14 55.28(18) . . . . ?
C4 C3 C19 C18 -127.25(16) . . . . ?
C4 C20 C21 C22 6.9(2) . . . . ?
C5 C2 C3 C4 -73.75(14) . . . . ?
C5 C2 C3 C19 44.69(17) . . . . ?
C5 C6 C7 C8 -171.98(15) . . . . ?
C5 C6 C11 C10 171.46(15) . . . . ?
C5 C13 C14 C15 -117.62(17) . . . . ?
C5 C13 C14 C19 59.79(17) . . . . ?
C5 C13 C20 C4 -53.56(16) . . . . ?
C5 C13 C20 C21 -179.76(13) . . . . ?
C6 C5 C13 C14 62.41(17) . . . . ?
C6 C5 C13 C20 179.78(12) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C6 C11 C10 -2.5(2) . . . . ?
C7 C8 C9 C10 -2.4(2) . . . . ?
C7 C8 C9 C12 176.02(16) . . . . ?
C8 C9 C10 C11 2.1(2) . . . . ?
C9 C10 C11 C6 0.3(2) . . . . ?
C11 C6 C7 C8 2.3(2) . . . . ?
C12 C9 C10 C11 -176.26(16) . . . . ?
C13 C5 C6 C7 94.82(17) . . . . ?
C13 C5 C6 C11 -79.07(18) . . . . ?
C13 C14 C15 C16 175.96(15) . . . . ?
C13 C14 C19 C3 0.34(19) . . . . ?
C13 C14 C19 C18 -177.29(14) . . . . ?
C13 C20 C21 C22 129.41(17) . . . . ?
C14 C13 C20 C4 64.19(16) . . . . ?
C14 C13 C20 C21 -62.02(16) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C14 C19 C3 177.96(14) . . . . ?
C15 C14 C19 C18 0.3(2) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -1.6(2) . . . . ?
C17 C18 C19 C3 -176.20(15) . . . . ?
C17 C18 C19 C14 1.1(2) . . . . ?
C19 C3 C4 N1 -161.19(13) . . . . ?
C19 C3 C4 C20 -46.63(17) . . . . ?
C19 C3 C4 C24 81.32(17) . . . . ?
C19 C14 C15 C16 -1.3(2) . . . . ?
C20 C4 C24 C23 11.9(2) . . . . ?
C20 C13 C14 C15 122.32(17) . . . . ?
C20 C13 C14 C19 -60.27(16) . . . . ?
C20 C21 C22 C23 2.4(3) . . . . ?
C21 C22 C23 C24 -5.0(3) . . . . ?
C22 C23 C24 C4 -2.8(3) . . . . ?
C24 C4 C20 C13 -136.59(14) . . . . ?
C24 C4 C20 C21 -13.4(2) . . . . ?
C25 N1 C1 O1 13.9(3) . . . . ?
C25 N1 C1 C2 -164.75(14) . . . . ?
C25 N1 C4 C3 -168.83(14) . . . . ?
C25 N1 C4 C20 76.84(18) . . . . ?
C25 N1 C4 C24 -51.4(2) . . . . ?
C26 C2 C3 C4 156.16(14) . . . . ?
C26 C2 C3 C19 -85.41(17) . . . . ?
C26 C2 C5 C6 20.1(2) . . . . ?
C26 C2 C5 C13 143.18(14) . . . . ?

_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 1.857
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_k11111-jjw-b(tpb-83)_auto
_database_code_depnum_ccdc_archive 'CCDC 2226539'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University Taiwan
Taiwan
;
_audit_update_record             
;
2022-12-14 deposited with the CCDC.	2025-12-26 downloaded from the CCDC.
;
_audit_creation_date             2022-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 N2 O2'
_chemical_formula_sum            'C25 H20 N2 O2'
_chemical_formula_weight         380.43
_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      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                   10.3481(3)
_cell_length_b                   11.4470(3)
_cell_length_c                   15.7580(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.878(2)
_cell_angle_gamma                90
_cell_volume                     1864.25(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13635
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9510
_cell_measurement_theta_min      2.0020
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.970
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00 100.00   0.50   29.29    --   10.60  57.00  60.00  240
  2  ω    -79.00  36.00   0.50   29.29    --   10.60 -77.00 -60.00  230
  3  ω    -79.00  38.00   0.50   29.29    --   10.60 -82.00  60.00  234
  4  ω    -15.00 100.00   0.50   29.29    --   10.60  77.00  60.00  230
  5  ω    -79.00  38.00   0.50   29.29    --   10.60 -82.00-120.00  234
  6  ω    -79.00  36.00   0.50   29.29    --   10.60 -77.00 150.00  230
  7  ω    -15.00 100.00   0.50   29.29    --   10.60  77.00-120.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0193254000
_diffrn_orient_matrix_UB_12      0.0545429000
_diffrn_orient_matrix_UB_13      -0.0164484000
_diffrn_orient_matrix_UB_21      0.0317665000
_diffrn_orient_matrix_UB_22      0.0137261000
_diffrn_orient_matrix_UB_23      0.0396803000
_diffrn_orient_matrix_UB_31      0.0577933000
_diffrn_orient_matrix_UB_32      -0.0259185000
_diffrn_orient_matrix_UB_33      -0.0135419000
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2857
_reflns_number_total             3284
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.090
_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)+(0.0517P)²+0.5789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C3(H3), C10(H10), C9(H9), C8(H8), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C13(H13), C16(H16), C20(H20), C5(H5), C21(H21), C22(H22),
 C6(H6), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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
O1 O -0.09297(9) 0.42286(9) 0.83814(7) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.17419(11) 0.89921(9) 0.86403(7) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.03080(11) 0.57285(10) 0.89693(8) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.14369(13) 0.21517(11) 0.80609(8) 0.0275(3) Uani 1 1 d . . . . .
C12 C 0.36515(13) 0.58623(12) 0.76912(9) 0.0184(3) Uani 1 1 d . . . . .
C18 C 0.20609(14) 0.43690(12) 0.65238(9) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.13949(13) 0.44309(12) 0.81195(9) 0.0170(3) Uani 1 1 d . . . . .
C17 C 0.36840(13) 0.51981(12) 0.84341(9) 0.0179(3) Uani 1 1 d . . . . .
C24 C 0.14578(13) 0.31513(13) 0.80749(9) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.00883(13) 0.47587(12) 0.84982(9) 0.0190(3) Uani 1 1 d . . . . .
C11 C 0.14895(13) 0.50673(12) 0.72349(9) 0.0174(3) Uani 1 1 d . . . . .
H11 H 0.059467 0.530609 0.703759 0.021 Uiso 1 1 calc R U . . .
C3 C 0.23817(13) 0.50019(12) 0.87771(8) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.245324 0.453595 0.931423 0.020 Uiso 1 1 calc R U . . .
C19 C 0.31287(13) 0.36256(12) 0.66311(9) 0.0208(3) Uani 1 1 d . . . . .
H19 H 0.350477 0.349358 0.718516 0.025 Uiso 1 1 calc R U . . .
C10 C 0.23001(13) 0.62080(12) 0.73969(9) 0.0183(3) Uani 1 1 d . . . . .
H10 H 0.232120 0.667401 0.686100 0.022 Uiso 1 1 calc R U . . .
C4 C 0.16391(13) 0.61765(12) 0.89141(9) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.17082(14) 0.69461(12) 0.81018(9) 0.0186(3) Uani 1 1 d . . . . .
H9 H 0.079898 0.713706 0.790494 0.022 Uiso 1 1 calc R U . . .
C23 C 0.15374(15) 0.45481(12) 0.56996(9) 0.0222(3) Uani 1 1 d . . . . .
H23 H 0.081018 0.504815 0.561211 0.027 Uiso 1 1 calc R U . . .
C13 C 0.47936(14) 0.60746(13) 0.72875(10) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.478147 0.653198 0.678413 0.029 Uiso 1 1 calc R U . . .
C16 C 0.48446(14) 0.47410(13) 0.87733(9) 0.0219(3) Uani 1 1 d . . . . .
H16 H 0.486244 0.429164 0.928062 0.026 Uiso 1 1 calc R U . . .
C20 C 0.36474(15) 0.30774(13) 0.59396(10) 0.0247(3) Uani 1 1 d . . . . .
H20 H 0.436725 0.256796 0.602331 0.030 Uiso 1 1 calc R U . . .
C8 C 0.24268(14) 0.80888(12) 0.82142(10) 0.0230(3) Uani 1 1 d . . . . .
H8 H 0.292565 0.834771 0.772051 0.028 Uiso 1 1 calc R U . . .
C5 C 0.21046(14) 0.67347(13) 0.97360(9) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.195793 0.632838 1.024799 0.028 Uiso 1 1 calc R U . . .
C21 C 0.31158(16) 0.32728(13) 0.51278(10) 0.0274(4) Uani 1 1 d . . . . .
H21 H 0.347441 0.290231 0.465416 0.033 Uiso 1 1 calc R U . . .
C22 C 0.20590(16) 0.40102(13) 0.50076(10) 0.0274(4) Uani 1 1 d . . . . .
H22 H 0.169340 0.414632 0.445135 0.033 Uiso 1 1 calc R U . . .
C6 C 0.27064(15) 0.77563(14) 0.97957(10) 0.0269(4) Uani 1 1 d . . . . .
H6 H 0.301351 0.802328 1.033993 0.032 Uiso 1 1 calc R U . . .
C15 C 0.59735(15) 0.49502(13) 0.83613(10) 0.0273(4) Uani 1 1 d . . . . .
H15 H 0.676895 0.463607 0.858554 0.033 Uiso 1 1 calc R U . . .
C25 C -0.07229(15) 0.64583(13) 0.92704(10) 0.0261(4) Uani 1 1 d . . . . .
H25A H -0.074940 0.719720 0.895597 0.039 Uiso 1 1 calc R U . . .
H25B H -0.056179 0.661643 0.987772 0.039 Uiso 1 1 calc R U . . .
H25C H -0.155290 0.605321 0.918062 0.039 Uiso 1 1 calc R U . . .
C14 C 0.59524(15) 0.56145(14) 0.76239(11) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.673290 0.575536 0.734803 0.034 Uiso 1 1 calc R U . . .
C7 C 0.29161(15) 0.84940(13) 0.90457(10) 0.0265(4) Uani 1 1 d . . . . .
H7 H 0.371136 0.899157 0.906412 0.032 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
O1 C1 1.2217(17) . ?
O2 C8 1.4388(18) . ?
O2 C7 1.4600(18) . ?
N1 C1 1.3484(19) . ?
N1 C4 1.4764(18) . ?
N1 C25 1.4533(19) . ?
N2 C24 1.1446(19) . ?
C12 C17 1.395(2) . ?
C12 C10 1.5041(19) . ?
C12 C13 1.391(2) . ?
C18 C11 1.520(2) . ?
C18 C19 1.398(2) . ?
C18 C23 1.397(2) . ?
C2 C24 1.4681(19) . ?
C2 C1 1.5512(19) . ?
C2 C11 1.5801(19) . ?
C2 C3 1.5613(18) . ?
C17 C3 1.494(2) . ?
C17 C16 1.392(2) . ?
C11 H11 1.0000 . ?
C11 C10 1.5659(19) . ?
C3 H3 1.0000 . ?
C3 C4 1.5689(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C10 H10 1.0000 . ?
C10 C9 1.546(2) . ?
C4 C9 1.5585(19) . ?
C4 C5 1.5018(19) . ?
C9 H9 1.0000 . ?
C9 C8 1.511(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.386(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C8 H8 1.0000 . ?
C8 C7 1.457(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.326(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.477(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.388(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C14 H14 0.9500 . ?
C7 H7 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C7 60.32(9) . . ?
C1 N1 C4 112.68(11) . . ?
C1 N1 C25 123.14(12) . . ?
C25 N1 C4 121.47(12) . . ?
C17 C12 C10 112.65(12) . . ?
C13 C12 C17 119.58(13) . . ?
C13 C12 C10 127.66(13) . . ?
C19 C18 C11 124.42(12) . . ?
C23 C18 C11 117.46(12) . . ?
C23 C18 C19 117.96(13) . . ?
C24 C2 C1 107.54(11) . . ?
C24 C2 C11 114.39(11) . . ?
C24 C2 C3 114.86(11) . . ?
C1 C2 C11 108.77(11) . . ?
C1 C2 C3 101.36(11) . . ?
C3 C2 C11 108.97(11) . . ?
C12 C17 C3 113.67(12) . . ?
C16 C17 C12 120.74(13) . . ?
C16 C17 C3 125.54(13) . . ?
N2 C24 C2 175.95(16) . . ?
O1 C1 N1 127.75(13) . . ?
O1 C1 C2 125.70(13) . . ?
N1 C1 C2 106.55(11) . . ?
C18 C11 C2 116.84(11) . . ?
C18 C11 H11 107.6 . . ?
C18 C11 C10 109.49(11) . . ?
C2 C11 H11 107.6 . . ?
C10 C11 C2 107.28(10) . . ?
C10 C11 H11 107.6 . . ?
C2 C3 H3 110.9 . . ?
C2 C3 C4 98.13(10) . . ?
C17 C3 C2 113.24(11) . . ?
C17 C3 H3 110.9 . . ?
C17 C3 C4 112.20(11) . . ?
C4 C3 H3 110.9 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.96(13) . . ?
C20 C19 H19 119.5 . . ?
C12 C10 C11 108.24(11) . . ?
C12 C10 H10 110.0 . . ?
C12 C10 C9 108.54(11) . . ?
C11 C10 H10 110.0 . . ?
C9 C10 C11 110.15(11) . . ?
C9 C10 H10 110.0 . . ?
N1 C4 C3 100.10(10) . . ?
N1 C4 C9 109.03(11) . . ?
N1 C4 C5 110.90(12) . . ?
C9 C4 C3 109.18(11) . . ?
C5 C4 C3 110.19(11) . . ?
C5 C4 C9 116.22(12) . . ?
C10 C9 C4 108.50(11) . . ?
C10 C9 H9 107.3 . . ?
C4 C9 H9 107.3 . . ?
C8 C9 C10 110.30(12) . . ?
C8 C9 C4 115.83(11) . . ?
C8 C9 H9 107.3 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.22(14) . . ?
C22 C23 H23 119.4 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.72(15) . . ?
C14 C13 H13 120.1 . . ?
C17 C16 H16 120.4 . . ?
C15 C16 C17 119.12(14) . . ?
C15 C16 H16 120.4 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.04(14) . . ?
C21 C20 H20 120.0 . . ?
O2 C8 C9 115.21(12) . . ?
O2 C8 H8 115.8 . . ?
O2 C8 C7 60.56(9) . . ?
C9 C8 H8 115.8 . . ?
C7 C8 C9 121.88(13) . . ?
C7 C8 H8 115.8 . . ?
C4 C5 H5 117.8 . . ?
C6 C5 C4 124.44(14) . . ?
C6 C5 H5 117.8 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.89(14) . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 119.92(14) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.32(14) . . ?
C7 C6 H6 118.8 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.58(14) . . ?
C14 C15 H15 119.7 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.25(15) . . ?
C15 C14 H14 119.9 . . ?
O2 C7 C6 114.88(13) . . ?
O2 C7 H7 117.1 . . ?
C8 C7 O2 59.12(9) . . ?
C8 C7 C6 118.63(13) . . ?
C8 C7 H7 117.1 . . ?
C6 C7 H7 117.1 . . ?

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
O2 C8 C7 C6 103.42(15) . . . . ?
N1 C4 C9 C10 -99.86(13) . . . . ?
N1 C4 C9 C8 135.50(12) . . . . ?
N1 C4 C5 C6 -134.14(15) . . . . ?
C12 C17 C3 C2 55.67(15) . . . . ?
C12 C17 C3 C4 -54.31(15) . . . . ?
C12 C17 C16 C15 -0.2(2) . . . . ?
C12 C10 C9 C4 -61.97(14) . . . . ?
C12 C10 C9 C8 65.89(14) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C18 C11 C10 C12 -63.07(14) . . . . ?
C18 C11 C10 C9 178.41(11) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C18 C23 C22 C21 0.4(2) . . . . ?
C2 C11 C10 C12 64.64(14) . . . . ?
C2 C11 C10 C9 -53.88(14) . . . . ?
C2 C3 C4 N1 43.06(12) . . . . ?
C2 C3 C4 C9 -71.31(13) . . . . ?
C2 C3 C4 C5 159.90(11) . . . . ?
C17 C12 C10 C11 -59.25(15) . . . . ?
C17 C12 C10 C9 60.29(15) . . . . ?
C17 C12 C13 C14 0.6(2) . . . . ?
C17 C3 C4 N1 162.32(11) . . . . ?
C17 C3 C4 C9 47.95(14) . . . . ?
C17 C3 C4 C5 -80.83(14) . . . . ?
C17 C16 C15 C14 0.5(2) . . . . ?
C24 C2 C1 O1 -34.42(18) . . . . ?
C24 C2 C1 N1 145.73(11) . . . . ?
C24 C2 C11 C18 -19.47(17) . . . . ?
C24 C2 C11 C10 -142.77(12) . . . . ?
C24 C2 C3 C17 84.76(15) . . . . ?
C24 C2 C3 C4 -156.76(12) . . . . ?
C1 N1 C4 C3 -31.00(14) . . . . ?
C1 N1 C4 C9 83.48(13) . . . . ?
C1 N1 C4 C5 -147.32(12) . . . . ?
C1 C2 C11 C18 -139.70(12) . . . . ?
C1 C2 C11 C10 97.00(12) . . . . ?
C1 C2 C3 C17 -159.66(11) . . . . ?
C1 C2 C3 C4 -41.18(12) . . . . ?
C11 C18 C19 C20 -175.64(13) . . . . ?
C11 C18 C23 C22 175.43(13) . . . . ?
C11 C2 C1 O1 89.96(16) . . . . ?
C11 C2 C1 N1 -89.89(13) . . . . ?
C11 C2 C3 C17 -45.07(15) . . . . ?
C11 C2 C3 C4 73.41(12) . . . . ?
C11 C10 C9 C4 56.37(14) . . . . ?
C11 C10 C9 C8 -175.77(11) . . . . ?
C3 C2 C1 O1 -155.30(13) . . . . ?
C3 C2 C1 N1 24.85(13) . . . . ?
C3 C2 C11 C18 110.61(13) . . . . ?
C3 C2 C11 C10 -12.69(14) . . . . ?
C3 C17 C16 C15 176.79(13) . . . . ?
C3 C4 C9 C10 8.59(15) . . . . ?
C3 C4 C9 C8 -116.06(13) . . . . ?
C3 C4 C5 C6 115.96(16) . . . . ?
C19 C18 C11 C2 -40.61(19) . . . . ?
C19 C18 C11 C10 81.54(16) . . . . ?
C19 C18 C23 C22 -0.2(2) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C10 C12 C17 C3 -1.18(16) . . . . ?
C10 C12 C17 C16 176.19(12) . . . . ?
C10 C12 C13 C14 -175.35(13) . . . . ?
C10 C9 C8 O2 160.99(11) . . . . ?
C10 C9 C8 C7 -129.31(14) . . . . ?
C4 N1 C1 O1 -175.79(13) . . . . ?
C4 N1 C1 C2 4.05(15) . . . . ?
C4 C9 C8 O2 -75.30(16) . . . . ?
C4 C9 C8 C7 -5.61(19) . . . . ?
C4 C5 C6 C7 3.7(2) . . . . ?
C9 C4 C5 C6 -8.9(2) . . . . ?
C9 C8 C7 O2 -103.00(15) . . . . ?
C9 C8 C7 C6 0.4(2) . . . . ?
C23 C18 C11 C2 144.09(13) . . . . ?
C23 C18 C11 C10 -93.76(14) . . . . ?
C23 C18 C19 C20 -0.4(2) . . . . ?
C13 C12 C17 C3 -177.67(12) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
C13 C12 C10 C11 116.90(15) . . . . ?
C13 C12 C10 C9 -123.56(15) . . . . ?
C16 C17 C3 C2 -121.55(14) . . . . ?
C16 C17 C3 C4 128.48(14) . . . . ?
C16 C15 C14 C13 -0.3(2) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C8 O2 C7 C6 -109.76(15) . . . . ?
C5 C4 C9 C10 133.95(12) . . . . ?
C5 C4 C9 C8 9.30(18) . . . . ?
C5 C6 C7 O2 67.84(19) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C25 N1 C1 O1 -14.3(2) . . . . ?
C25 N1 C1 C2 165.57(12) . . . . ?
C25 N1 C4 C3 167.13(12) . . . . ?
C25 N1 C4 C9 -78.39(15) . . . . ?
C25 N1 C4 C5 50.81(17) . . . . ?
C7 O2 C8 C9 113.87(14) . . . . ?

_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 2.870
_oxdiff_exptl_absorpt_empirical_full_min 0.605
####################################################################### 
# 
# 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_d25138
_database_code_depnum_ccdc_archive 'CCDC 2377178'
loop_
_audit_author_name
_audit_author_address
CCDC
;Kaohsiung Medical University 
Taiwan
;
_audit_update_record             
;
2024-08-13 deposited with the CCDC.	2025-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 N2 O'
_chemical_formula_sum            'C27 H24 N2 O'
_chemical_formula_weight         392.48

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   10.5513(6)
_cell_length_b                   10.5230(6)
_cell_length_c                   22.0654(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.639(2)
_cell_angle_gamma                90.00
_cell_volume                     2415.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.88

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37341
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.07
_reflns_number_total             4280
_reflns_number_gt                3793
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0951P)²+1.2656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4280
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.132
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21250(16) 0.83473(18) 0.17374(8) 0.0320(4) Uani 1 1 d . . .
C2 C 0.09135(18) 0.6678(2) 0.11219(10) 0.0465(5) Uani 1 1 d . . .
H2A H 0.0911 0.6430 0.0694 0.070 Uiso 1 1 calc R . .
H2B H 0.0174 0.7229 0.1145 0.070 Uiso 1 1 calc R . .
H2C H 0.0861 0.5917 0.1372 0.070 Uiso 1 1 calc R . .
C3 C 0.33791(16) 0.68185(17) 0.13257(8) 0.0307(4) Uani 1 1 d . . .
C4 C 0.34440(17) 0.63273(19) 0.06937(8) 0.0360(4) Uani 1 1 d . . .
H4 H 0.3116 0.6843 0.0350 0.043 Uiso 1 1 calc R . .
C5 C 0.39391(18) 0.5205(2) 0.05943(8) 0.0388(4) Uani 1 1 d . . .
H5 H 0.3965 0.4961 0.0182 0.047 Uiso 1 1 calc R . .
C6 C 0.44505(19) 0.43176(19) 0.10897(9) 0.0398(4) Uani 1 1 d . . .
C7 C 0.5069(2) 0.3093(2) 0.09231(11) 0.0540(6) Uani 1 1 d . . .
H7A H 0.5432 0.2640 0.1306 0.065 Uiso 1 1 calc R . .
H7B H 0.5790 0.3305 0.0706 0.065 Uiso 1 1 calc R . .
C8 C 0.4145(3) 0.2208(3) 0.05193(15) 0.0808(9) Uani 1 1 d . . .
H8A H 0.4623 0.1485 0.0391 0.121 Uiso 1 1 calc R . .
H8B H 0.3724 0.2671 0.0155 0.121 Uiso 1 1 calc R . .
H8C H 0.3493 0.1898 0.0752 0.121 Uiso 1 1 calc R . .
C9 C 0.4358(2) 0.46237(18) 0.16673(9) 0.0401(5) Uani 1 1 d . . .
H9 H 0.4707 0.4051 0.1984 0.048 Uiso 1 1 calc R . .
C10 C 0.37377(18) 0.58172(17) 0.18468(8) 0.0339(4) Uani 1 1 d . . .
H10 H 0.2922 0.5564 0.1989 0.041 Uiso 1 1 calc R . .
C11 C 0.46007(18) 0.64837(17) 0.23982(8) 0.0342(4) Uani 1 1 d . . .
H11 H 0.4798 0.5884 0.2753 0.041 Uiso 1 1 calc R . .
C12 C 0.58180(17) 0.69010(17) 0.21938(8) 0.0349(4) Uani 1 1 d . . .
C13 C 0.7072(2) 0.6588(2) 0.24557(10) 0.0496(5) Uani 1 1 d . . .
H13 H 0.7229 0.6000 0.2786 0.060 Uiso 1 1 calc R . .
C14 C 0.8087(2) 0.7139(2) 0.22308(13) 0.0598(7) Uani 1 1 d . . .
H14 H 0.8943 0.6933 0.2412 0.072 Uiso 1 1 calc R . .
C15 C 0.7874(2) 0.7986(3) 0.17452(13) 0.0593(7) Uani 1 1 d . . .
H15 H 0.8582 0.8367 0.1599 0.071 Uiso 1 1 calc R . .
C16 C 0.66275(19) 0.8279(2) 0.14715(10) 0.0457(5) Uani 1 1 d . . .
H16 H 0.6475 0.8844 0.1131 0.055 Uiso 1 1 calc R . .
C17 C 0.56091(17) 0.77402(17) 0.16991(8) 0.0334(4) Uani 1 1 d . . .
C18 C 0.42222(16) 0.80338(17) 0.14789(8) 0.0297(4) Uani 1 1 d . . .
H18 H 0.4118 0.8628 0.1120 0.036 Uiso 1 1 calc R . .
C19 C 0.35553(16) 0.85691(16) 0.20023(8) 0.0293(4) Uani 1 1 d . . .
C20 C 0.37812(16) 0.99269(18) 0.21128(8) 0.0336(4) Uani 1 1 d . . .
C21 C 0.38864(17) 0.76825(17) 0.25897(8) 0.0321(4) Uani 1 1 d . . .
H21 H 0.3048 0.7379 0.2690 0.038 Uiso 1 1 calc R . .
C22 C 0.46144(18) 0.82803(18) 0.31705(8) 0.0355(4) Uani 1 1 d . . .
C23 C 0.4137(2) 0.8085(2) 0.37152(9) 0.0461(5) Uani 1 1 d . . .
H23 H 0.3347 0.7647 0.3704 0.055 Uiso 1 1 calc R . .
C24 C 0.4797(3) 0.8520(2) 0.42727(10) 0.0576(6) Uani 1 1 d . . .
H24 H 0.4464 0.8366 0.4640 0.069 Uiso 1 1 calc R . .
C25 C 0.5940(3) 0.9178(2) 0.42960(10) 0.0579(6) Uani 1 1 d . . .
H25 H 0.6394 0.9475 0.4678 0.070 Uiso 1 1 calc R . .
C26 C 0.6417(2) 0.9400(2) 0.37558(11) 0.0514(6) Uani 1 1 d . . .
H26 H 0.7198 0.9856 0.3768 0.062 Uiso 1 1 calc R . .
C27 C 0.57584(19) 0.89569(19) 0.31990(9) 0.0399(5) Uani 1 1 d . . .
H27 H 0.6091 0.9117 0.2832 0.048 Uiso 1 1 calc R . .
N1 N 0.20932(14) 0.73606(15) 0.13522(7) 0.0359(4) Uani 1 1 d . . .
N2 N 0.39177(17) 1.10038(17) 0.21687(9) 0.0479(5) Uani 1 1 d . . .
O1 O 0.12130(12) 0.89297(13) 0.18738(6) 0.0417(4) Uani 1 1 d . . .


_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 O1 1.220(2) . ?
C1 N1 1.339(2) . ?
C1 C19 1.542(2) . ?
C2 N1 1.453(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N1 1.482(2) . ?
C3 C4 1.500(2) . ?
C3 C10 1.559(3) . ?
C3 C18 1.562(2) . ?
C4 C5 1.325(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.470(3) . ?
C5 H5 0.9500 . ?
C6 C9 1.334(3) . ?
C6 C7 1.517(3) . ?
C7 C8 1.524(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.500(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.559(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.497(3) . ?
C11 C21 1.564(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.392(3) . ?
C12 C17 1.393(3) . ?
C13 C14 1.381(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.495(2) . ?
C18 C19 1.555(2) . ?
C18 H18 1.0000 . ?
C19 C20 1.462(3) . ?
C19 C21 1.588(2) . ?
C20 N2 1.146(3) . ?
C21 C22 1.516(2) . ?
C21 H21 1.0000 . ?
C22 C27 1.394(3) . ?
C22 C23 1.394(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
O1 C1 N1 127.53(16) . . ?
O1 C1 C19 126.34(16) . . ?
N1 C1 C19 106.07(14) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 110.74(14) . . ?
N1 C3 C10 109.99(14) . . ?
C4 C3 C10 114.19(15) . . ?
N1 C3 C18 99.68(13) . . ?
C4 C3 C18 111.74(14) . . ?
C10 C3 C18 109.55(13) . . ?
C5 C4 C3 122.82(18) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 123.30(17) . . ?
C4 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C9 C6 C5 118.74(18) . . ?
C9 C6 C7 122.7(2) . . ?
C5 C6 C7 118.59(18) . . ?
C6 C7 C8 113.7(2) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 C10 124.02(18) . . ?
C6 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
C9 C10 C3 115.72(15) . . ?
C9 C10 C11 111.04(16) . . ?
C3 C10 C11 108.03(14) . . ?
C9 C10 H10 107.2 . . ?
C3 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C12 C11 C10 108.39(14) . . ?
C12 C11 C21 108.76(14) . . ?
C10 C11 C21 109.20(15) . . ?
C12 C11 H11 110.2 . . ?
C10 C11 H11 110.2 . . ?
C21 C11 H11 110.2 . . ?
C13 C12 C17 119.34(19) . . ?
C13 C12 C11 127.57(19) . . ?
C17 C12 C11 113.02(15) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C12 120.97(18) . . ?
C16 C17 C18 125.13(18) . . ?
C12 C17 C18 113.80(16) . . ?
C17 C18 C19 111.93(14) . . ?
C17 C18 C3 113.09(14) . . ?
C19 C18 C3 98.35(13) . . ?
C17 C18 H18 111.0 . . ?
C19 C18 H18 111.0 . . ?
C3 C18 H18 111.0 . . ?
C20 C19 C1 109.45(14) . . ?
C20 C19 C18 113.36(14) . . ?
C1 C19 C18 101.51(13) . . ?
C20 C19 C21 115.50(14) . . ?
C1 C19 C21 106.74(14) . . ?
C18 C19 C21 109.17(13) . . ?
N2 C20 C19 176.2(2) . . ?
C22 C21 C11 111.36(15) . . ?
C22 C21 C19 117.21(14) . . ?
C11 C21 C19 107.67(13) . . ?
C22 C21 H21 106.7 . . ?
C11 C21 H21 106.7 . . ?
C19 C21 H21 106.7 . . ?
C27 C22 C23 118.13(18) . . ?
C27 C22 C21 124.23(17) . . ?
C23 C22 C21 117.57(18) . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.4(2) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 120.2(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 120.9(2) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C1 N1 C2 122.29(15) . . ?
C1 N1 C3 113.45(14) . . ?
C2 N1 C3 122.16(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050
