# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_am-278
_database_code_depnum_ccdc_archive 'CCDC 2525368'
loop_
_audit_author_name
_audit_author_address
'Darina Ildarovna Nasyrova'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2026-01-23 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_audit_creation_date             2025-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N2 O3, C H Cl3'
_chemical_formula_sum            'C24 H17 Cl3 N2 O3'
_chemical_formula_weight         487.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H17O3N2Cl3
_chemical_oxdiff_usercomment     AM-278
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'
Cl Cl 0.3639 0.7018 '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      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                   10.17070(10)
_cell_length_b                   30.9855(4)
_cell_length_c                   7.13450(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.806(2)
_cell_angle_gamma                90
_cell_volume                     2115.39(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10643
_cell_measurement_temperature    99.96(16)
_cell_measurement_theta_max      78.8200
_cell_measurement_theta_min      2.8480
_shelx_estimated_absorpt_T_max   0.633
_shelx_estimated_absorpt_T_min   0.348
_exptl_absorpt_coefficient_mu    4.188
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.106a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -12 1 0.0759
4 0 -4 0.1447
4 13 1 0.0590
-4 3 4 0.1438
6 -8 0 0.0759
2 2 -5 0.1313
-6 8 1 0.0297
6 7 -1 0.0765
-6 -3 3 0.1131
1 20 -1 0.0860
-1 -20 0 0.0646
-4 -10 4 0.1360
4 -14 0 0.0692
2 -14 2 0.1143
2 -19 -1 0.0637
-4 14 3 0.0941

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.2592 -11.9858 0.7850 -0.2157 -0.8978 0.3840
4.3852 -0.4593 -4.2991 0.0162 0.0544 -0.9984
4.2577 13.3648 0.6410 0.2320 0.9700 -0.0734
-3.5666 3.1168 4.4530 0.0298 0.1379 0.9900
5.7950 -7.9511 -0.2076 0.9142 0.1716 -0.3671
2.1852 1.9328 -4.6088 -0.3621 -0.0648 -0.9299
-5.9489 7.7755 0.5683 -0.8831 -0.1660 0.4389
6.0829 7.1880 -0.7708 0.4541 0.7753 -0.4390
-5.9548 -3.2523 3.1626 -0.2487 -0.4280 0.8689
1.0059 19.8161 -0.5913 -0.5061 0.8565 -0.1015
-0.6729 -20.0108 0.2378 0.5084 -0.8609 0.0204
-3.7786 -10.0912 3.7235 0.2829 -0.4746 0.8335
4.4282 -14.1528 -0.0433 0.9398 -0.1910 -0.2833
2.2114 -13.5981 2.3266 0.9473 -0.1909 0.2573
2.1794 -18.9726 -0.6711 0.7182 -0.6328 -0.2895
-3.7107 14.3368 2.7140 -0.5212 0.4572 0.7207

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            16251
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.612
_diffrn_reflns_theta_min         2.852
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00 -22.00   0.50    1.50    --  -90.00  45.00-150.00   54
  2  ω    -31.00  26.00   0.50    0.50    --  -48.26  25.00 -73.00  114
  3  ω    -19.00  25.00   0.50    0.50    --  -48.26  19.00   0.00   88
  4  ω    -80.00 -20.00   0.50    1.50    --  -90.00  99.00  88.00  120
  5  ω    -24.00  20.00   0.50    0.50    --   48.26 -19.00   0.00   88
  6  ω     67.00 101.00   0.50    1.50    --  111.50 -77.00-120.00   68
  7  ω     60.00  86.00   0.50    1.50    --  111.50 -77.00 -60.00   52
  8  ω     40.00  65.00   0.50    1.50    --  111.50 -61.00  60.00   50
  9  ω     40.00  65.00   0.50    1.50    --  111.50 -77.00  90.00   50
 10  ω     40.00  65.00   0.50    1.50    --  111.50 -61.00  90.00   50
 11  ω     40.00  92.00   0.50    1.50    --  111.50 -77.00 150.00  104
 12  ω     79.00 104.00   0.50    1.50    --  111.50 -77.00  90.00   50
 13  ω     43.00  71.00   0.50    1.50    --  111.50 -61.00   0.00   56
 14  ω     59.00  85.00   0.50    1.50    --  111.50 -95.00  30.00   52
 15  ω     41.00 106.00   0.50    1.50    --  111.50 -99.00 -17.00  130
 16  ω     41.00 113.00   0.50    1.50    --  111.50-127.00 -93.00  144
 17  ω     75.00 101.00   0.50    1.50    --  111.50-125.00  90.00   52
 18  ω     42.00  69.00   0.50    1.50    --  111.50-125.00  90.00   54
 19  ω    143.00 170.00   0.50    1.50    --  111.50  15.00   0.00   54
 20  ω    105.00 173.00   0.50    1.50    --  111.50  25.00 -73.00  136
 21  ω    102.00 132.00   0.50    1.50    --  111.50  15.00   0.00   60
 22  ω     38.00 123.00   0.50    0.50    --   48.26  25.00 -73.00  170
 23  ω    100.00 145.00   0.50    1.50    --  111.50  77.00-180.00   90
 24  ω    152.00 178.00   0.50    1.50    --  111.50 125.00-180.00   52
 25  ω     95.00 137.00   0.50    1.50    --  111.50 125.00-180.00   84
 26  ω     94.00 145.00   0.50    1.50    --  111.50 127.00 -17.00  102
 27  ω    106.00 132.00   0.50    1.50    --  111.50 125.00  60.00   52
 28  ω    153.00 178.00   0.50    1.50    --  111.50 125.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1237284000
_diffrn_orient_matrix_UB_12      -0.0280773000
_diffrn_orient_matrix_UB_13      0.1254479000
_diffrn_orient_matrix_UB_21      0.0883642000
_diffrn_orient_matrix_UB_22      0.0409176000
_diffrn_orient_matrix_UB_23      0.0731142000
_diffrn_orient_matrix_UB_31      -0.0530358000
_diffrn_orient_matrix_UB_32      0.0028759000
_diffrn_orient_matrix_UB_33      0.1778281000
_diffrn_oxdiff_digest_od_ed      
;

;
_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                4016
_reflns_number_total             4376
_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 1.171.44.106a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.106a 64-bit (release 18-04-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.106a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.7909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0852
_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:
 C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C10(H10), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.39592(4) 0.54534(2) 1.05999(6) 0.03149(11) Uani 1 1 d . . . . .
Cl2 Cl 0.15565(4) 0.56420(2) 0.70721(6) 0.03195(11) Uani 1 1 d . . . . .
Cl3 Cl 0.43473(4) 0.57965(2) 0.70708(7) 0.03932(12) Uani 1 1 d . . . . .
O1 O 0.42878(10) 0.78623(3) 0.24923(14) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.31493(11) 0.66169(3) 0.10395(15) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.63497(12) 0.56385(3) 0.48596(16) 0.0277(2) Uani 1 1 d . . . . .
N1 N 0.92982(13) 0.79421(4) 0.64760(18) 0.0237(3) Uani 1 1 d . . . . .
N2 N 0.89912(13) 0.75260(4) 0.62592(18) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.83014(14) 0.82453(5) 0.5722(2) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.69250(14) 0.81356(5) 0.4643(2) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.623796 0.835101 0.409031 0.024 Uiso 1 1 calc R U . . .
C3 C 0.65930(14) 0.76997(5) 0.44033(19) 0.0180(3) Uani 1 1 d . . . . .
C4 C 0.52203(14) 0.75387(5) 0.32659(19) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.29502(14) 0.77612(5) 0.13267(19) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.25583(14) 0.73504(5) 0.0864(2) 0.0192(3) Uani 1 1 d . . . . .
H6 H 0.162559 0.729317 0.003118 0.023 Uiso 1 1 calc R U . . .
C7 C 0.35048(14) 0.69911(5) 0.15882(19) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.49119(14) 0.71077(5) 0.29791(19) 0.0172(3) Uani 1 1 d . . . . .
C9 C 0.59949(14) 0.67940(5) 0.40011(19) 0.0183(3) Uani 1 1 d . . . . .
C10 C 0.57141(15) 0.63504(5) 0.3977(2) 0.0213(3) Uani 1 1 d . . . . .
H10 H 0.480313 0.624677 0.325810 0.026 Uiso 1 1 calc R U . . .
C11 C 0.67555(16) 0.60611(5) 0.4993(2) 0.0228(3) Uani 1 1 d . . . . .
C12 C 0.81078(16) 0.62048(5) 0.6047(2) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.881826 0.600517 0.672733 0.029 Uiso 1 1 calc R U . . .
C13 C 0.83956(15) 0.66390(5) 0.6087(2) 0.0239(3) Uani 1 1 d . . . . .
H13 H 0.931428 0.673724 0.680101 0.029 Uiso 1 1 calc R U . . .
C14 C 0.73645(14) 0.69404(5) 0.5099(2) 0.0198(3) Uani 1 1 d . . . . .
C15 C 0.76631(14) 0.73978(5) 0.52548(19) 0.0193(3) Uani 1 1 d . . . . .
C16 C 0.87691(15) 0.87007(5) 0.6077(2) 0.0210(3) Uani 1 1 d . . . . .
C17 C 0.78320(15) 0.90264(5) 0.6102(2) 0.0234(3) Uani 1 1 d . . . . .
H17 H 0.688553 0.895548 0.590338 0.028 Uiso 1 1 calc R U . . .
C18 C 0.82636(17) 0.94530(5) 0.6415(2) 0.0264(3) Uani 1 1 d . . . . .
H18 H 0.761479 0.967259 0.642812 0.032 Uiso 1 1 calc R U . . .
C19 C 0.96470(17) 0.95585(5) 0.6709(2) 0.0285(3) Uani 1 1 d . . . . .
H19 H 0.994621 0.985036 0.692641 0.034 Uiso 1 1 calc R U . . .
C20 C 1.05931(16) 0.92363(6) 0.6686(2) 0.0289(3) Uani 1 1 d . . . . .
H20 H 1.153847 0.930892 0.688596 0.035 Uiso 1 1 calc R U . . .
C21 C 1.01617(15) 0.88079(5) 0.6371(2) 0.0250(3) Uani 1 1 d . . . . .
H21 H 1.081121 0.858877 0.635532 0.030 Uiso 1 1 calc R U . . .
C22 C 0.20787(15) 0.81547(5) 0.0717(2) 0.0231(3) Uani 1 1 d . . . . .
H22A H 0.117091 0.807744 -0.026139 0.035 Uiso 1 1 calc R U . . .
H22B H 0.255104 0.836182 0.012335 0.035 Uiso 1 1 calc R U . . .
H22C H 0.193834 0.828469 0.188747 0.035 Uiso 1 1 calc R U . . .
C23 C 0.73692(19) 0.53237(5) 0.5891(2) 0.0321(4) Uani 1 1 d . . . . .
H23A H 0.694143 0.503631 0.567895 0.048 Uiso 1 1 calc R U . . .
H23B H 0.771302 0.538962 0.731893 0.048 Uiso 1 1 calc R U . . .
H23C H 0.815062 0.532968 0.538108 0.048 Uiso 1 1 calc R U . . .
C24 C 0.32629(16) 0.57986(5) 0.8543(2) 0.0261(3) Uani 1 1 d . . . . .
H24 H 0.322787 0.609845 0.904185 0.031 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
Cl1 C24 1.7594(16) . ?
Cl2 C24 1.7648(16) . ?
Cl3 C24 1.7618(16) . ?
O1 C4 1.3620(17) . ?
O1 C5 1.3689(16) . ?
O2 C7 1.2378(18) . ?
O3 C11 1.3666(19) . ?
O3 C23 1.4322(19) . ?
N1 N2 1.3231(19) . ?
N1 C1 1.353(2) . ?
N2 C15 1.3564(18) . ?
C1 C2 1.3921(19) . ?
C1 C16 1.483(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 C4 1.4452(19) . ?
C3 C15 1.407(2) . ?
C4 C8 1.371(2) . ?
C5 C6 1.341(2) . ?
C5 C22 1.483(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.448(2) . ?
C7 C8 1.4836(18) . ?
C8 C9 1.4646(19) . ?
C9 C10 1.403(2) . ?
C9 C14 1.4213(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(2) . ?
C11 C12 1.398(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.403(2) . ?
C14 C15 1.446(2) . ?
C16 C17 1.392(2) . ?
C16 C21 1.400(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24 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
C4 O1 C5 119.34(11) . . ?
C11 O3 C23 117.90(13) . . ?
N2 N1 C1 120.99(12) . . ?
N1 N2 C15 120.03(13) . . ?
N1 C1 C2 121.86(14) . . ?
N1 C1 C16 116.05(12) . . ?
C2 C1 C16 122.08(13) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.56(13) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 C4 123.59(13) . . ?
C2 C3 C15 118.24(13) . . ?
C15 C3 C4 118.13(13) . . ?
O1 C4 C3 112.39(12) . . ?
O1 C4 C8 124.33(12) . . ?
C8 C4 C3 123.28(13) . . ?
O1 C5 C22 111.23(12) . . ?
C6 C5 O1 121.20(13) . . ?
C6 C5 C22 127.57(13) . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.40(13) . . ?
C7 C6 H6 118.8 . . ?
O2 C7 C6 121.32(12) . . ?
O2 C7 C8 123.50(13) . . ?
C6 C7 C8 115.17(12) . . ?
C4 C8 C7 117.20(12) . . ?
C4 C8 C9 118.46(12) . . ?
C9 C8 C7 124.31(12) . . ?
C10 C9 C8 121.90(13) . . ?
C10 C9 C14 118.49(13) . . ?
C14 C9 C8 119.59(13) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.64(14) . . ?
C11 C10 H10 119.7 . . ?
O3 C11 C10 115.02(14) . . ?
O3 C11 C12 124.15(13) . . ?
C10 C11 C12 120.83(14) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.10(14) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.55(14) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C15 119.76(13) . . ?
C13 C14 C9 119.38(14) . . ?
C13 C14 C15 120.80(13) . . ?
N2 C15 C3 121.29(14) . . ?
N2 C15 C14 118.26(13) . . ?
C3 C15 C14 120.45(12) . . ?
C17 C16 C1 120.69(13) . . ?
C17 C16 C21 119.23(14) . . ?
C21 C16 C1 120.08(14) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.81(14) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.84(16) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.92(15) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.33(14) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 120.1 . . ?
C20 C21 C16 119.87(15) . . ?
C20 C21 H21 120.1 . . ?
C5 C22 H22A 109.5 . . ?
C5 C22 H22B 109.5 . . ?
C5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Cl1 C24 Cl2 111.44(9) . . ?
Cl1 C24 Cl3 109.80(8) . . ?
Cl1 C24 H24 108.7 . . ?
Cl2 C24 H24 108.7 . . ?
Cl3 C24 Cl2 109.44(8) . . ?
Cl3 C24 H24 108.7 . . ?

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 C4 C8 C7 5.64(19) . . . . ?
O1 C4 C8 C9 -176.32(11) . . . . ?
O1 C5 C6 C7 1.2(2) . . . . ?
O2 C7 C8 C4 172.10(13) . . . . ?
O2 C7 C8 C9 -5.8(2) . . . . ?
O3 C11 C12 C13 -179.67(13) . . . . ?
N1 N2 C15 C3 0.9(2) . . . . ?
N1 N2 C15 C14 -178.35(12) . . . . ?
N1 C1 C2 C3 1.6(2) . . . . ?
N1 C1 C16 C17 -154.62(13) . . . . ?
N1 C1 C16 C21 26.02(18) . . . . ?
N2 N1 C1 C2 -1.8(2) . . . . ?
N2 N1 C1 C16 179.43(12) . . . . ?
C1 N1 N2 C15 0.5(2) . . . . ?
C1 C2 C3 C4 -177.89(12) . . . . ?
C1 C2 C3 C15 -0.24(19) . . . . ?
C1 C16 C17 C18 -179.39(13) . . . . ?
C1 C16 C21 C20 179.44(13) . . . . ?
C2 C1 C16 C17 26.7(2) . . . . ?
C2 C1 C16 C21 -152.71(13) . . . . ?
C2 C3 C4 O1 -1.19(18) . . . . ?
C2 C3 C4 C8 177.70(13) . . . . ?
C2 C3 C15 N2 -0.99(19) . . . . ?
C2 C3 C15 C14 178.20(12) . . . . ?
C3 C4 C8 C7 -173.11(12) . . . . ?
C3 C4 C8 C9 4.93(19) . . . . ?
C4 O1 C5 C6 -2.86(18) . . . . ?
C4 O1 C5 C22 177.02(11) . . . . ?
C4 C3 C15 N2 176.79(12) . . . . ?
C4 C3 C15 C14 -4.01(18) . . . . ?
C4 C8 C9 C10 172.31(12) . . . . ?
C4 C8 C9 C14 -5.98(19) . . . . ?
C5 O1 C4 C3 178.10(11) . . . . ?
C5 O1 C4 C8 -0.77(19) . . . . ?
C5 C6 C7 O2 -175.23(13) . . . . ?
C5 C6 C7 C8 3.66(19) . . . . ?
C6 C7 C8 C4 -6.75(17) . . . . ?
C6 C7 C8 C9 175.34(12) . . . . ?
C7 C8 C9 C10 -9.8(2) . . . . ?
C7 C8 C9 C14 171.90(12) . . . . ?
C8 C9 C10 C11 -178.71(13) . . . . ?
C8 C9 C14 C13 179.53(12) . . . . ?
C8 C9 C14 C15 2.19(19) . . . . ?
C9 C10 C11 O3 179.79(12) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C9 C14 C15 N2 -177.93(12) . . . . ?
C9 C14 C15 C3 2.85(19) . . . . ?
C10 C9 C14 C13 1.18(19) . . . . ?
C10 C9 C14 C15 -176.15(12) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C9 -1.1(2) . . . . ?
C12 C13 C14 C15 176.25(13) . . . . ?
C13 C14 C15 N2 4.77(19) . . . . ?
C13 C14 C15 C3 -174.45(12) . . . . ?
C14 C9 C10 C11 -0.4(2) . . . . ?
C15 C3 C4 O1 -178.85(11) . . . . ?
C15 C3 C4 C8 0.04(19) . . . . ?
C16 C1 C2 C3 -179.71(12) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C16 C21 C20 0.1(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C19 C20 C21 C16 0.0(2) . . . . ?
C21 C16 C17 C18 0.0(2) . . . . ?
C22 C5 C6 C7 -178.70(13) . . . . ?
C23 O3 C11 C10 -179.35(13) . . . . ?
C23 O3 C11 C12 1.0(2) . . . . ?

_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 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.858
####################################################################### 
# 
# 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_di-40me-ph
_database_code_depnum_ccdc_archive 'CCDC 2525369'
loop_
_audit_author_name
_audit_author_address
'Darina Ildarovna Nasyrova'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2026-01-23 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_audit_creation_date             2025-04-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 O6'
_chemical_formula_sum            'C23 H18 O6'
_chemical_formula_weight         390.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H18O6
_chemical_oxdiff_usercomment     Di-40Me-Ph
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'
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                   8.0262(2)
_cell_length_b                   10.3038(3)
_cell_length_c                   12.5236(3)
_cell_angle_alpha                66.963(2)
_cell_angle_beta                 80.090(2)
_cell_angle_gamma                89.957(2)
_cell_volume                     936.35(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10980
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      79.5390
_cell_measurement_theta_min      3.8940
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.319
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.99a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 -8 0.0680
5 2 3 0.1821
0 2 8 0.0792
-4 0 4 0.1472
-1 -6 -6 0.1089
3 -5 -1 0.1083
5 0 5 0.1485
0 6 6 0.1292
-4 4 0 0.1835
-5 0 -5 0.1503
3 -3 5 0.1008
0 -6 1 0.1235
-3 -6 -3 0.1250
-1 5 -3 0.1143
2 6 2 0.1700
2 -1 7 0.0873
-1 2 -6 0.0810
3 4 0 0.1879
0 0 7 0.0623
-1 -1 6 0.0763
1 -2 -8 0.0785
3 -5 -3 0.1032
-1 6 0 0.1131

_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.4167 -1.6653 -7.9973 -0.1788 -0.7399 0.6485
4.9827 1.8964 2.7740 -0.1060 -0.4553 -0.8840
-0.0791 1.5023 7.8539 0.1926 0.7985 -0.5703
-3.7622 -0.2603 3.9440 0.2260 0.9488 0.2207
-1.3947 -5.6873 -6.4106 0.5501 -0.3942 0.7362
3.4639 -4.9792 -1.0382 0.7793 -0.5535 -0.2938
4.6521 0.0322 4.5708 0.2920 -0.2043 -0.9344
0.0425 6.2529 5.5924 -0.6996 0.4997 -0.5108
-3.9784 4.2000 -0.1559 -0.7245 0.5139 0.4595
-4.6494 -0.0548 -4.5881 -0.2893 0.2024 0.9356
2.7679 -2.5353 5.1035 0.7189 0.1491 -0.6789
-0.3171 -5.7485 0.9124 0.9767 0.1996 0.0790
-2.6614 -5.7301 -2.8824 0.7412 0.1497 0.6544
-0.7739 5.0480 -2.5026 -0.9619 -0.1974 0.1890
2.0112 5.9926 1.7661 -0.8516 -0.1728 -0.4949
1.5906 -1.2276 6.7097 0.5858 0.4694 -0.6607
-1.1179 1.6969 -6.4245 -0.6414 -0.5134 0.5702
3.2580 4.3290 -0.2773 -0.6846 -0.5441 -0.4851
0.2720 -0.2553 7.2856 0.4483 0.7083 -0.5453
-1.2428 -1.1787 6.1254 0.5190 0.8180 -0.2480
0.9025 -2.4439 -7.6414 -0.0209 -0.8857 0.4638
3.4977 -4.8131 -2.6385 0.6639 -0.7237 -0.1883
-0.5573 6.2332 0.2695 -0.9975 0.0423 -0.0560

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24394
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.703
_diffrn_reflns_theta_min         3.904
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  24.00   0.50    0.20    --  -48.13  79.00 123.00  188
  2  ω    -21.00  71.00   0.50    0.20    --   48.13 -79.00  -0.00  184
  3  ω   -112.00 -18.00   0.50    1.00    --  -90.00  79.00 123.00  188
  4  ω   -161.00 -79.00   0.50    1.00    --  -90.00 -79.00  -0.00  164
  5  ω     40.00 134.00   0.50    1.00    --  111.50 -79.00  -0.00  188
  6  ω    101.00 178.00   0.50    1.00    --  111.50  79.00 123.00  154
  7  ω    -70.00  24.00   0.50    0.20    --  -48.13  77.00-150.00  188
  8  ω    -27.00  26.00   0.50    0.20    --  -48.13  19.00 120.00  106
  9  ω    -27.00  26.00   0.50    0.20    --  -48.13  19.00  60.00  106
 10  ω    -70.00  24.00   0.50    0.20    --  -48.13  77.00-150.00  188
 11  ω    -27.00  26.00   0.50    0.20    --  -48.13  19.00-150.00  106
 12  ω    -27.00  26.00   0.50    0.20    --  -48.13  19.00-180.00  106
 13  ω    -51.00 -18.00   0.50    1.00    --  -90.00  45.00   0.00   66
 14  ω    -51.00 -18.00   0.50    1.00    --  -90.00  45.00 -30.00   66
 15  ω    -71.00 -18.00   0.50    1.00    --  -90.00  61.00 -60.00  106
 16  ω    -51.00 -18.00   0.50    1.00    --  -90.00  45.00  90.00   66
 17  ω     96.00 178.00   0.50    1.00    --  111.50  61.00  60.00  164
 18  ω    101.00 178.00   0.50    1.00    --  111.50  45.00 -90.00  154
 19  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00 -60.00  130
 20  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00 -60.00  130
 21  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00-150.00  130
 22  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00 -30.00  130
 23  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00-120.00  130
 24  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00-150.00  130
 25  ω     40.00  71.00   0.50    1.00    --  111.50 -61.00 -60.00   62
 26  ω     90.00 178.00   0.50    1.00    --  111.50  77.00 -60.00  176
 27  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00  90.00  130
 28  ω    101.00 178.00   0.50    1.00    --  111.50  30.00 -90.00  154
 29  ω     40.00 135.00   0.50    1.00    --  111.50 -81.00 -29.54  190
 30  ω     40.00 135.00   0.50    1.00    --  111.50 -81.00 -29.54  190
 31  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00 -90.00  130
 32  ω     40.00 105.00   0.50    1.00    --  111.50 -95.00-180.00  130
 33  ω     42.00 111.00   0.50    1.00    --  111.50-125.00-150.00  138
 34  ω     42.00 111.00   0.50    1.00    --  111.50-125.00 -30.00  138
 35  ω    101.00 178.00   0.50    1.00    --  111.50  45.00 -60.00  154
 36  ω    101.00 178.00   0.50    1.00    --  111.50  30.00-120.00  154
 37  ω    101.00 178.00   0.50    1.00    --  111.50  45.00  30.00  154
 38  ω     40.00  71.00   0.50    1.00    --  111.50 -61.00 120.00   62
 39  ω     40.00 105.00   0.50    1.00    --  111.50 -77.00 120.00  130
 40  ω     41.00  67.00   0.50    1.00    --  111.50 -61.00-180.00   52
 41  ω    102.00 157.00   0.50    1.00    --  111.50  45.00   0.00  110
 42  ω     66.00 103.00   0.50    1.00    --  111.50 -95.00 120.00   74
 43  ω     78.00 111.00   0.50    1.00    --  111.50-125.00 150.00   66
 44  ω     98.00 174.00   0.50    1.00    --  111.50 125.00   0.00  152
 45  ω     80.00 111.00   0.50    1.00    --  111.50-125.00  60.00   62
 46  ω    138.00 164.00   0.50    1.00    --  111.50  77.00 -60.00   52
 47  ω     43.00  68.00   0.50    1.00    --  111.50 -61.00  30.00   50
 48  ω     75.00 101.00   0.50    1.00    --  111.50 -95.00  60.00   52
 49  ω     45.00  71.00   0.50    1.00    --  111.50-125.00  60.00   52
 50  ω     42.00 104.00   0.50    1.00    --  111.50-125.00  90.00  124
 51  ω     74.00 105.00   0.50    1.00    --  111.50 -95.00 150.00   62
 52  ω    115.00 159.00   0.50    1.00    --  111.50  77.00 -90.00   88
 53  ω     56.00  82.00   0.50    1.00    --  111.50  -2.00  85.76   52
 54  ω    118.00 159.00   0.50    1.00    --  111.50  -2.00  85.76   82
 55  ω     41.00  67.00   0.50    1.00    --  111.50 -77.00-180.00   52
 56  ω     60.00  86.00   0.50    1.00    --  111.50 -77.00-150.00   52
 57  ω     43.00  87.00   0.50    1.00    --  111.50 -77.00 -60.00   88
 58  ω     43.00  75.00   0.50    1.00    --  111.50 -77.00   0.00   64
 59  ω     42.00  68.00   0.50    1.00    --  111.50 -77.00  60.00   52
 60  ω     85.00 111.00   0.50    1.00    --  111.50-125.00-180.00   52
 61  ω     96.00 125.00   0.50    1.00    --  111.50 125.00 120.00   58
 62  ω     43.00  74.00   0.50    1.00    --  111.50-125.00 -30.00   62
 63  ω    152.00 177.00   0.50    1.00    --  111.50 125.00-150.00   50
 64  ω    102.00 170.00   0.50    1.00    --  111.50  45.00 120.00  136
 65  ω    132.00 158.00   0.50    1.00    --  111.50  30.00 150.00   52
 66  ω    103.00 129.00   0.50    1.00    --  111.50  61.00 -30.00   52
 67  ω    104.00 145.00   0.50    1.00    --  111.50  61.00 150.00   82
 68  ω    110.00 147.00   0.50    1.00    --  111.50 125.00-150.00   74
 69  ω    144.00 169.00   0.50    1.00    --  111.50  30.00-120.00   50
 70  ω    104.00 147.00   0.50    1.00    --  111.50  45.00-180.00   86
 71  ω    142.00 168.00   0.50    1.00    --  111.50 125.00 120.00   52
 72  ω     95.00 126.00   0.50    1.00    --  111.50 125.00 150.00   62
 73  ω    139.00 165.00   0.50    1.00    --  111.50 125.00 150.00   52
 74  ω     81.00 107.00   0.50    1.00    --  111.50 -84.00 138.60   52
 75  ω     42.00  70.00   0.50    1.00    --  111.50 -61.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0093218000
_diffrn_orient_matrix_UB_12      -0.1616035000
_diffrn_orient_matrix_UB_13      0.0555273000
_diffrn_orient_matrix_UB_21      -0.1442911000
_diffrn_orient_matrix_UB_22      -0.0105360000
_diffrn_orient_matrix_UB_23      0.1022342000
_diffrn_orient_matrix_UB_31      -0.1313975000
_diffrn_orient_matrix_UB_32      -0.0176884000
_diffrn_orient_matrix_UB_33      -0.0705572000
_diffrn_oxdiff_digest_od_ed      
;

;
_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                3752
_reflns_number_total             4028
_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 1.171.44.99a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.144a 64-bit (release 23-01-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.99a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.068
_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)+(0.1009P)²+0.2034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1495
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

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 0.85380(13) 0.73112(9) 0.42818(8) 0.0279(2) Uani 1 1 d . . . . .
O2 O 0.99839(13) 1.04687(10) 0.10621(9) 0.0321(2) Uani 1 1 d . . . . .
O3 O 0.96173(13) 0.77658(10) 0.12353(9) 0.0310(2) Uani 1 1 d . . . . .
H3 H 0.980(3) 0.853(3) 0.057(2) 0.061(7) Uiso 1 1 d . . . . .
O4 O 1.08349(12) 0.48290(10) 0.24606(9) 0.0305(2) Uani 1 1 d . . . . .
O5 O 0.48854(12) 0.28950(10) 0.05607(9) 0.0301(2) Uani 1 1 d . . . . .
O6 O 0.81529(13) 0.24448(10) 0.44663(9) 0.0325(2) Uani 1 1 d . . . . .
C1 C 0.86760(17) 0.86645(13) 0.41885(12) 0.0276(3) Uani 1 1 d . . . . .
C2 C 0.92074(18) 0.97492(14) 0.31379(12) 0.0286(3) Uani 1 1 d . . . . .
H2 H 0.935070 1.067831 0.310886 0.034 Uiso 1 1 calc R U . . .
C3 C 0.95597(17) 0.95240(14) 0.20643(12) 0.0273(3) Uani 1 1 d . . . . .
C4 C 0.93522(17) 0.80467(14) 0.22059(12) 0.0266(3) Uani 1 1 d . . . . .
C5 C 0.88773(17) 0.69952(13) 0.33015(12) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.86320(16) 0.54765(13) 0.36102(12) 0.0264(3) Uani 1 1 d . . . . .
C7 C 0.93054(17) 0.49152(13) 0.26706(11) 0.0263(3) Uani 1 1 d . . . . .
C8 C 0.80972(16) 0.44912(13) 0.20846(11) 0.0257(3) Uani 1 1 d . . . . .
C9 C 0.63639(17) 0.46363(14) 0.23204(12) 0.0277(3) Uani 1 1 d . . . . .
H9 H 0.594683 0.509386 0.282959 0.033 Uiso 1 1 calc R U . . .
C10 C 0.52320(17) 0.41281(14) 0.18290(12) 0.0278(3) Uani 1 1 d . . . . .
H10 H 0.405135 0.422922 0.200169 0.033 Uiso 1 1 calc R U . . .
C11 C 0.58593(17) 0.34650(13) 0.10755(11) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.75971(17) 0.33465(14) 0.08028(12) 0.0283(3) Uani 1 1 d . . . . .
H12 H 0.801924 0.292250 0.026923 0.034 Uiso 1 1 calc R U . . .
C13 C 0.86981(17) 0.38444(14) 0.13073(12) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.987925 0.374957 0.112784 0.033 Uiso 1 1 calc R U . . .
C14 C 0.30850(17) 0.28531(15) 0.08887(14) 0.0330(3) Uani 1 1 d . . . . .
H14A H 0.254290 0.240751 0.046082 0.050 Uiso 1 1 calc R U . . .
H14B H 0.273425 0.381836 0.068990 0.050 Uiso 1 1 calc R U . . .
H14C H 0.274275 0.230459 0.174056 0.050 Uiso 1 1 calc R U . . .
C15 C 0.79419(18) 0.46008(14) 0.47258(12) 0.0289(3) Uani 1 1 d . . . . .
H15 H 0.764983 0.499615 0.529681 0.035 Uiso 1 1 calc R U . . .
C16 C 0.76160(17) 0.30575(14) 0.51066(12) 0.0281(3) Uani 1 1 d . . . . .
C17 C 0.65489(17) 0.22665(13) 0.62935(12) 0.0275(3) Uani 1 1 d . . . . .
C18 C 0.56008(18) 0.10324(14) 0.64703(13) 0.0304(3) Uani 1 1 d . . . . .
H18 H 0.563617 0.073762 0.583715 0.036 Uiso 1 1 calc R U . . .
C19 C 0.46163(18) 0.02433(15) 0.75594(13) 0.0335(3) Uani 1 1 d . . . . .
H19 H 0.396889 -0.058640 0.767113 0.040 Uiso 1 1 calc R U . . .
C20 C 0.4572(2) 0.06620(16) 0.84914(13) 0.0363(3) Uani 1 1 d . . . . .
H20 H 0.389706 0.011632 0.924062 0.044 Uiso 1 1 calc R U . . .
C21 C 0.5512(2) 0.18767(16) 0.83297(13) 0.0350(3) Uani 1 1 d . . . . .
H21 H 0.548746 0.215478 0.897118 0.042 Uiso 1 1 calc R U . . .
C22 C 0.64882(18) 0.26859(14) 0.72353(12) 0.0300(3) Uani 1 1 d . . . . .
H22 H 0.711523 0.352459 0.712495 0.036 Uiso 1 1 calc R U . . .
C23 C 0.81438(19) 0.87321(14) 0.53598(12) 0.0316(3) Uani 1 1 d . . . . .
H23A H 0.832593 0.970731 0.528330 0.047 Uiso 1 1 calc R U . . .
H23B H 0.881520 0.811536 0.591503 0.047 Uiso 1 1 calc R U . . .
H23C H 0.693875 0.841816 0.565429 0.047 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 1.3560(15) . ?
O1 C5 1.3729(15) . ?
O2 C3 1.2393(17) . ?
O3 H3 0.88(3) . ?
O3 C4 1.3391(16) . ?
O4 C7 1.2211(16) . ?
O5 C11 1.3572(16) . ?
O5 C14 1.4285(16) . ?
O6 C16 1.2265(17) . ?
C1 C2 1.349(2) . ?
C1 C23 1.4843(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.4335(18) . ?
C3 C4 1.4680(17) . ?
C4 C5 1.3634(19) . ?
C5 C6 1.4621(17) . ?
C6 C7 1.5246(17) . ?
C6 C15 1.3493(19) . ?
C7 C8 1.4719(18) . ?
C8 C9 1.3921(18) . ?
C8 C13 1.4035(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3870(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.3969(18) . ?
C11 C12 1.3948(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3747(19) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.4795(18) . ?
C16 C17 1.4905(19) . ?
C17 C18 1.4029(18) . ?
C17 C22 1.3998(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 O1 C5 121.19(11) . . ?
C4 O3 H3 113.8(16) . . ?
C11 O5 C14 118.06(11) . . ?
O1 C1 C23 110.71(11) . . ?
C2 C1 O1 121.56(12) . . ?
C2 C1 C23 127.72(12) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.12(12) . . ?
C3 C2 H2 119.4 . . ?
O2 C3 C2 125.05(12) . . ?
O2 C3 C4 119.64(12) . . ?
C2 C3 C4 115.30(12) . . ?
O3 C4 C3 118.39(12) . . ?
O3 C4 C5 121.19(11) . . ?
C5 C4 C3 120.41(12) . . ?
O1 C5 C6 111.73(11) . . ?
C4 C5 O1 120.32(11) . . ?
C4 C5 C6 127.94(12) . . ?
C5 C6 C7 118.16(11) . . ?
C15 C6 C5 119.98(12) . . ?
C15 C6 C7 121.67(11) . . ?
O4 C7 C6 117.21(11) . . ?
O4 C7 C8 123.79(12) . . ?
C8 C7 C6 119.00(11) . . ?
C9 C8 C7 122.48(12) . . ?
C9 C8 C13 118.55(12) . . ?
C13 C8 C7 118.88(12) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.50(12) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.80(12) . . ?
C11 C10 H10 120.6 . . ?
O5 C11 C10 124.61(12) . . ?
O5 C11 C12 114.94(11) . . ?
C12 C11 C10 120.45(12) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.89(12) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.76(12) . . ?
C12 C13 H13 119.6 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C15 H15 118.3 . . ?
C6 C15 C16 123.47(12) . . ?
C16 C15 H15 118.3 . . ?
O6 C16 C15 121.98(13) . . ?
O6 C16 C17 120.56(12) . . ?
C15 C16 C17 117.43(11) . . ?
C18 C17 C16 117.98(12) . . ?
C22 C17 C16 122.83(12) . . ?
C22 C17 C18 119.17(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.40(13) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.06(13) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.10(14) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.27(14) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.00(13) . . ?
C21 C22 H22 120.0 . . ?
C1 C23 H23A 109.5 . . ?
C1 C23 H23B 109.5 . . ?
C1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.88(3) 1.87(3) 2.6976(14) 155(2) 2_775 yes

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 3.5(2) . . . . ?
O1 C5 C6 C7 -167.32(11) . . . . ?
O1 C5 C6 C15 7.77(18) . . . . ?
O2 C3 C4 O3 -0.56(19) . . . . ?
O2 C3 C4 C5 -179.65(13) . . . . ?
O3 C4 C5 O1 -177.08(11) . . . . ?
O3 C4 C5 C6 1.8(2) . . . . ?
O4 C7 C8 C9 -178.28(12) . . . . ?
O4 C7 C8 C13 5.32(19) . . . . ?
O5 C11 C12 C13 -177.79(11) . . . . ?
O6 C16 C17 C18 -26.28(19) . . . . ?
O6 C16 C17 C22 152.23(13) . . . . ?
C1 O1 C5 C4 -0.45(19) . . . . ?
C1 O1 C5 C6 -179.50(11) . . . . ?
C1 C2 C3 O2 176.88(13) . . . . ?
C1 C2 C3 C4 -1.87(19) . . . . ?
C2 C3 C4 O3 178.25(11) . . . . ?
C2 C3 C4 C5 -0.83(19) . . . . ?
C3 C4 C5 O1 2.0(2) . . . . ?
C3 C4 C5 C6 -179.14(12) . . . . ?
C4 C5 C6 C7 13.7(2) . . . . ?
C4 C5 C6 C15 -171.19(14) . . . . ?
C5 O1 C1 C2 -2.34(19) . . . . ?
C5 O1 C1 C23 176.60(11) . . . . ?
C5 C6 C7 O4 75.40(16) . . . . ?
C5 C6 C7 C8 -105.50(14) . . . . ?
C5 C6 C15 C16 178.65(12) . . . . ?
C6 C7 C8 C9 2.68(18) . . . . ?
C6 C7 C8 C13 -173.71(11) . . . . ?
C6 C15 C16 O6 9.6(2) . . . . ?
C6 C15 C16 C17 -168.32(13) . . . . ?
C7 C6 C15 C16 -6.4(2) . . . . ?
C7 C8 C9 C10 -174.83(12) . . . . ?
C7 C8 C13 C12 175.62(12) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C8 C13 C12 -0.92(19) . . . . ?
C9 C10 C11 O5 178.42(12) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C10 C11 C12 C13 2.1(2) . . . . ?
C11 C12 C13 C8 -0.9(2) . . . . ?
C13 C8 C9 C10 1.6(2) . . . . ?
C14 O5 C11 C10 -5.87(19) . . . . ?
C14 O5 C11 C12 174.01(11) . . . . ?
C15 C6 C7 O4 -99.60(15) . . . . ?
C15 C6 C7 C8 79.50(16) . . . . ?
C15 C16 C17 C18 151.65(13) . . . . ?
C15 C16 C17 C22 -29.84(19) . . . . ?
C16 C17 C18 C19 178.73(12) . . . . ?
C16 C17 C22 C21 -177.85(13) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C17 C22 C21 0.6(2) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 C17 -1.0(2) . . . . ?
C22 C17 C18 C19 0.2(2) . . . . ?
C23 C1 C2 C3 -175.26(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 2.034
_oxdiff_exptl_absorpt_empirical_full_min 0.604
