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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_laiyt2cult
_database_code_depnum_ccdc_archive 'CCDC 2300818'
loop_
_audit_author_name
_audit_author_address
'Shiqiang Ma'
;Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2026-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N O'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.25180(10)
_cell_length_b                   5.13270(10)
_cell_length_c                   15.4875(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.358(2)
_cell_angle_gamma                90
_cell_volume                     563.108(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7025
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7330
_cell_measurement_theta_min      5.8610
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (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_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8666
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.075
_diffrn_reflns_theta_min         2.921
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -7.00   1.00    3.00    --  -39.95 125.00-150.00   80
  2  ω    -27.00  34.00   1.00    3.00    --  -39.95  57.00  30.00   61
  3  ω    -66.00 -21.00   1.00    3.00    --  -39.95 125.00  30.00   45
  4  ω   -101.00  -1.00   1.00    3.00    --  -39.95 -23.00-129.56  100
  5  ω    -61.00  -6.00   1.00    3.00    --  -39.95 125.00 -90.00   55
  6  ω     85.00 114.00   1.00    3.00    --   39.95  57.00  30.00   29
  7  ω     47.00 106.00   1.00    3.00    --   39.95  57.00  90.00   59
  8  ω     10.00 110.00   1.00    3.00    --   39.95  57.00 150.00  100
  9  ω      3.00  28.00   1.00    3.00    --   39.95  87.00-164.23   25
 10  ω     28.00  95.00   1.00    3.00    --   39.95-125.00 150.00   67
 11  ω      5.00  32.00   1.00    3.00    --   39.95  85.00-137.64   27
 12  ω      3.00  29.00   1.00    3.00    --   39.95  89.00  92.03   26
 13  ω      4.00  29.00   1.00    3.00    --   39.95  89.00 -83.01   25
 14  ω     10.00  68.00   1.00    3.00    --   39.95  57.00  30.00   58
 15  ω    -33.00  50.00   1.00    3.00    --   39.95 -37.00 150.00   83
 16  ω     15.00  42.00   1.00    3.00    --   39.95  57.00  90.00   27
 17  ω      3.00  28.00   1.00    3.00    --   39.95  88.00   0.20   25
 18  ω     17.00  88.00   1.00    3.00    --   39.95  37.00 -90.00   71
 19  ω      3.00  28.00   1.00    3.00    --   39.95  87.00 -36.43   25
 20  ω     30.00  81.00   1.00    8.00    --  113.00 -94.00  60.00   51
 21  ω     84.00 110.00   1.00    8.00    --  113.00  61.00-120.00   26
 22  ω    138.00 165.00   1.00    8.00    --  113.00  57.00 172.85   27
 23  ω     83.00 175.00   1.00    8.00    --  113.00  61.00 120.00   92
 24  ω     29.00  77.00   1.00    8.00    --  113.00 -94.00-120.00   48
 25  ω     83.00 114.00   1.00    8.00    --  113.00  61.00 -60.00   31
 26  ω     85.00 115.00   1.00    8.00    --  113.00  45.00  90.00   30
 27  ω     86.00 111.00   1.00    8.00    --  113.00  45.00-150.00   25
 28  ω     83.00 110.00   1.00    8.00    --  113.00  61.00-150.00   27
 29  ω    125.00 178.00   1.00    8.00    --  113.00  61.00  60.00   53
 30  ω     87.00 148.00   1.00    8.00    --  113.00  45.00  30.00   61
 31  ω    117.00 163.00   1.00    8.00    --  113.00  62.00 100.72   46
 32  ω     83.00 112.00   1.00    8.00    --  113.00  57.00 172.85   29
 33  ω     37.00 108.00   1.00    8.00    --  113.00-111.00 120.00   71
 34  ω     84.00 109.00   1.00    8.00    --  113.00  61.00  90.00   25
 35  ω     82.00 112.00   1.00    8.00    --  113.00  62.00 100.72   30
 36  ω     29.00  75.00   1.00    8.00    --  113.00 -94.00 150.00   46
 37  ω    128.00 168.00   1.00    8.00    --  113.00  63.00 -13.68   40
 38  ω    153.00 178.00   1.00    8.00    --  113.00  42.00-136.78   25
 39  ω     86.00 112.00   1.00    8.00    --  113.00  45.00-120.00   26
 40  ω     86.00 135.00   1.00    8.00    --  113.00  45.00 -30.00   49
 41  ω     83.00 109.00   1.00    8.00    --  113.00  61.00-180.00   26
 42  ω     80.00 107.00   1.00    8.00    --  113.00 -94.00 150.00   27
 43  ω     82.00 108.00   1.00    8.00    --  113.00  63.00 -13.68   26
 44  ω     86.00 177.00   1.00    8.00    --  113.00  45.00 150.00   91
 45  ω     87.00 176.00   1.00    8.00    --  113.00  45.00 -60.00   89
 46  ω     83.00 109.00   1.00    8.00    --  113.00  61.00  60.00   26
 47  ω     83.00 162.00   1.00    8.00    --  113.00  61.00  30.00   79
 48  ω     33.00 105.00   1.00    8.00    --  113.00 -94.00 -90.00   72
 49  ω     83.00 109.00   1.00    8.00    --  113.00  61.00 150.00   26
 50  ω     84.00 113.00   1.00    8.00    --  113.00  61.00   0.00   29
 51  ω     85.00 167.00   1.00    8.00    --  113.00  45.00 -90.00   82
 52  ω     83.00 109.00   1.00    8.00    --  113.00  61.00 -30.00   26
 53  ω     83.00 109.00   1.00    8.00    --  113.00  61.00 -90.00   26
 54  ω     43.00 142.00   1.00    8.00    --  113.00 -61.00 -90.00   99
 55  ω     76.00 104.00   1.00    8.00    --  113.00 -94.00   0.00   28
 56  ω    105.00 177.00   1.00    8.00    --  113.00 111.00 -60.00   72
 57  ω     84.00 109.00   1.00    8.00    --  113.00  59.00  51.12   25
 58  ω    121.00 175.00   1.00    8.00    --  113.00  61.00-150.00   54
 59  ω     86.00 113.00   1.00    8.00    --  113.00  42.00-136.78   27
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1659568000
_diffrn_orient_matrix_UB_12      -0.1772657000
_diffrn_orient_matrix_UB_13      -0.0094464000
_diffrn_orient_matrix_UB_21      0.0814767000
_diffrn_orient_matrix_UB_22      0.0218950000
_diffrn_orient_matrix_UB_23      0.1001525000
_diffrn_orient_matrix_UB_31      -0.1147098000
_diffrn_orient_matrix_UB_32      -0.2409439000
_diffrn_orient_matrix_UB_33      0.0160491000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                2295
_reflns_number_total             2337
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.023
_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)+(0.0567P)²+0.1331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0896
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.06578(17) 0.2280(3) 0.28897(8) 0.0192(3) Uani 1 1 d . . . . .
O2 O 0.4778(2) 0.0974(3) 0.46705(8) 0.0242(3) Uani 1 1 d . . . . .
H2 H 0.4929 0.2500 0.4869 0.036 Uiso 1 1 calc R U . . .
C1 C 0.1642(3) 0.1982(4) 0.37892(11) 0.0191(4) Uani 1 1 d . . . . .
H1 H 0.1714 0.3709 0.4094 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3642(2) 0.1029(4) 0.37894(11) 0.0182(4) Uani 1 1 d . . . . .
H2A H 0.3557 -0.0783 0.3547 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4520(2) 0.2738(4) 0.32012(11) 0.0183(4) Uani 1 1 d . . . . .
H3 H 0.5847 0.2663 0.3251 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3508(2) 0.4359(3) 0.26112(11) 0.0155(3) Uani 1 1 d . . . . .
C5 C 0.4316(2) 0.6212(4) 0.20599(11) 0.0166(4) Uani 1 1 d . . . . .
C6 C 0.6195(2) 0.7050(4) 0.23218(12) 0.0206(4) Uani 1 1 d . . . . .
H6 H 0.6969 0.6351 0.2844 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6942(3) 0.8872(4) 0.18347(13) 0.0242(4) Uani 1 1 d . . . . .
H7 H 0.8215 0.9424 0.2023 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5818(3) 0.9894(4) 0.10672(13) 0.0235(4) Uani 1 1 d . . . . .
H8 H 0.6324 1.1139 0.0727 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3957(3) 0.9087(4) 0.08001(11) 0.0202(4) Uani 1 1 d . . . . .
H9 H 0.3196 0.9795 0.0277 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3182(2) 0.7249(4) 0.12884(11) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.1128(2) 0.6482(4) 0.09812(11) 0.0184(4) Uani 1 1 d . . . . .
H11A H 0.0880 0.6094 0.0341 0.022 Uiso 1 1 calc R U . . .
H11B H 0.0326 0.7979 0.1067 0.022 Uiso 1 1 calc R U . . .
C12 C 0.0563(2) 0.4121(4) 0.14661(11) 0.0177(4) Uani 1 1 d . . . . .
H12A H -0.0830 0.4005 0.1359 0.021 Uiso 1 1 calc R U . . .
H12B H 0.1041 0.2510 0.1239 0.021 Uiso 1 1 calc R U . . .
C13 C 0.1380(2) 0.4372(3) 0.24529(11) 0.0159(3) Uani 1 1 d . . . . .
H13 H 0.0956 0.6062 0.2667 0.019 Uiso 1 1 calc R U . . .
C14 C 0.0523(3) 0.0107(4) 0.42312(13) 0.0250(4) Uani 1 1 d . . . . .
H14A H -0.0733 0.0834 0.4217 0.037 Uiso 1 1 calc R U . . .
H14B H 0.1182 -0.0166 0.4846 0.037 Uiso 1 1 calc R U . . .
H14C H 0.0395 -0.1561 0.3916 0.037 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 1.431(2) . ?
O1 C13 1.427(2) . ?
O2 H2 0.8400 . ?
O2 C2 1.4354(19) . ?
C1 H1 1.0000 . ?
C1 C2 1.531(2) . ?
C1 C14 1.513(3) . ?
C2 H2A 1.0000 . ?
C2 C3 1.501(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.334(3) . ?
C4 C5 1.480(2) . ?
C4 C13 1.510(2) . ?
C5 C6 1.404(2) . ?
C5 C10 1.402(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.400(2) . ?
C10 C11 1.515(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.527(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C13 O1 C1 112.63(13) . . ?
C2 O2 H2 109.5 . . ?
O1 C1 H1 109.2 . . ?
O1 C1 C2 108.02(13) . . ?
O1 C1 C14 107.72(14) . . ?
C2 C1 H1 109.2 . . ?
C14 C1 H1 109.2 . . ?
C14 C1 C2 113.35(15) . . ?
O2 C2 C1 110.95(14) . . ?
O2 C2 H2A 108.4 . . ?
O2 C2 C3 110.91(14) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 C1 109.76(14) . . ?
C3 C2 H2A 108.4 . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.54(16) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 124.65(16) . . ?
C3 C4 C13 120.49(16) . . ?
C5 C4 C13 114.85(14) . . ?
C6 C5 C4 120.65(16) . . ?
C10 C5 C4 120.22(15) . . ?
C10 C5 C6 119.06(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.26(17) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.66(17) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.77(18) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.15(17) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 C11 121.76(16) . . ?
C9 C10 C5 119.10(16) . . ?
C9 C10 C11 119.12(15) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C10 C11 C12 113.63(14) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 C11 109.82(14) . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
O1 C13 C4 112.67(14) . . ?
O1 C13 C12 108.00(13) . . ?
O1 C13 H13 109.0 . . ?
C4 C13 C12 109.09(14) . . ?
C4 C13 H13 109.0 . . ?
C12 C13 H13 109.0 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 O2 173.37(14) . . . . ?
O1 C1 C2 C3 50.45(18) . . . . ?
O2 C2 C3 C4 -138.68(17) . . . . ?
C1 O1 C13 C4 46.51(19) . . . . ?
C1 O1 C13 C12 167.07(13) . . . . ?
C1 C2 C3 C4 -15.7(2) . . . . ?
C2 C3 C4 C5 175.59(16) . . . . ?
C2 C3 C4 C13 -5.4(3) . . . . ?
C3 C4 C5 C6 -22.3(3) . . . . ?
C3 C4 C5 C10 160.65(18) . . . . ?
C3 C4 C13 O1 -8.7(2) . . . . ?
C3 C4 C13 C12 -128.61(17) . . . . ?
C4 C5 C6 C7 -176.94(17) . . . . ?
C4 C5 C10 C9 177.14(16) . . . . ?
C4 C5 C10 C11 -1.3(3) . . . . ?
C5 C4 C13 O1 170.43(14) . . . . ?
C5 C4 C13 C12 50.50(19) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C5 C10 C11 C12 -12.2(2) . . . . ?
C6 C5 C10 C9 0.1(2) . . . . ?
C6 C5 C10 C11 -178.40(16) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C8 C9 C10 C11 178.49(18) . . . . ?
C9 C10 C11 C12 169.29(16) . . . . ?
C10 C5 C6 C7 0.1(3) . . . . ?
C10 C11 C12 C13 44.2(2) . . . . ?
C11 C12 C13 O1 173.97(14) . . . . ?
C11 C12 C13 C4 -63.26(18) . . . . ?
C13 O1 C1 C2 -68.47(18) . . . . ?
C13 O1 C1 C14 168.74(14) . . . . ?
C13 C4 C5 C6 158.59(16) . . . . ?
C13 C4 C5 C10 -18.4(2) . . . . ?
C14 C1 C2 O2 -67.35(19) . . . . ?
C14 C1 C2 C3 169.73(15) . . . . ?


_olex2_date_sample_data_collection 2023-06-26
_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 2.196
_oxdiff_exptl_absorpt_empirical_full_min 0.396
####################################################################### 
# 
# 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_yiqin3_Mo100K_auto
_database_code_depnum_ccdc_archive 'CCDC 2520928'
loop_
_audit_author_name
_audit_author_address
'Herman H Y SUNG'
;The Hong Kong University of Science and Thechnology
Hong Kong
;
_audit_update_record             
;
2026-01-07 deposited with the CCDC.	2026-04-20 downloaded from the CCDC.
;
_audit_creation_date             2025-11-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_chemical_formula_moiety         'C18 H22 N2 O5'
_chemical_formula_sum            'C18 H22 N2 O5'
_chemical_formula_weight         346.386
_chemical_oxdiff_formula         O3N3C20H20
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.1945(6)
_cell_length_b                   10.2575(5)
_cell_length_c                   10.3603(7)
_cell_angle_alpha                88.103(5)
_cell_angle_beta                 67.432(6)
_cell_angle_gamma                69.589(5)
_cell_volume                     839.89(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3329
_cell_measurement_temperature    99.94(13)
_cell_measurement_theta_max      29.0160
_cell_measurement_theta_min      2.9160
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             368.266
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.9921
_diffrn_reflns_Laue_measured_fraction_max 0.8285
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6051
_diffrn_reflns_point_group_measured_fraction_full 0.9921
_diffrn_reflns_point_group_measured_fraction_max 0.8285
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_min         2.68
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.94(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.8285
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  59.00   1.00   18.00    --  -10.49  57.00 -90.00   95
  2  ω    -78.00  13.00   1.00   18.00    --  -10.49 -57.00 120.00   91
  3  ω     39.00 100.00   1.00   18.00    --   10.80 178.00 120.00   61
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684426000
_diffrn_orient_matrix_UB_12      0.0615037000
_diffrn_orient_matrix_UB_13      0.0392689000
_diffrn_orient_matrix_UB_21      -0.0491201000
_diffrn_orient_matrix_UB_22      -0.0111303000
_diffrn_orient_matrix_UB_23      -0.0341168000
_diffrn_orient_matrix_UB_31      -0.0308000000
_diffrn_orient_matrix_UB_32      -0.0401482000
_diffrn_orient_matrix_UB_33      0.0535379000
_diffrn_oxdiff_digest_hkl        
;
0123bc696eedaa133ba6fb8b6180ab03436607
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3175
_reflns_number_total             3836
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2476
_refine_diff_density_min         -0.2887
_refine_diff_density_rms         0.0698
_refine_ls_d_res_high            0.7244
_refine_ls_d_res_low             7.5993
_refine_ls_goodness_of_fit_ref   1.0682
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     424
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.0682
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0053P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0422
_olex2_refinement_description    
;
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
- for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 6.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         B3LYP
   BASIS SET:      def2-SVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2025-11-18_16-44-06
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.64187(7) 0.08231(6) 0.25512(6) 0.01610(15) Uani 1.000000 .
O2 O 0.54252(7) 0.20698(6) 0.10189(6) 0.01427(14) Uani 1.000000 .
O3 O 0.12658(9) 0.09055(8) 0.64878(7) 0.02306(18) Uani 1.000000 .
H3 H 0.2181(14) 0.0301(13) 0.6744(13) 0.042(4) Uani 1.000000 .
O4 O -0.13798(8) 0.67877(7) 0.07660(7) 0.02785(18) Uani 1.000000 .
O5 O -0.38076(8) 0.78472(7) 0.24654(7) 0.02751(17) Uani 1.000000 .
N1 N 0.36029(8) 0.20253(8) 0.31698(7) 0.01358(17) Uani 1.000000 .
N2 N -0.25238(10) 0.68164(8) 0.18788(8) 0.01883(18) Uani 1.000000 .
C1 C 0.31721(13) 0.17543(11) 0.46306(10) 0.0153(2) Uani 1.000000 .
H1a H 0.4340(12) 0.1189(10) 0.4766(9) 0.026(3) Uani 1.000000 .
H1b H 0.2524(11) 0.2768(11) 0.5332(9) 0.025(3) Uani 1.000000 .
C2 C 0.19634(11) 0.09626(10) 0.50185(9) 0.0153(2) Uani 1.000000 .
H2 H 0.2657(11) -0.0108(10) 0.4435(9) 0.020(2) Uani 1.000000 .
C3 C 0.05148(11) 0.17379(9) 0.46130(9) 0.0142(2) Uani 1.000000 .
H3a H -0.0680(11) 0.1611(10) 0.5226(9) 0.028(3) Uani 1.000000 .
C4 C 0.06115(10) 0.26207(9) 0.36255(8) 0.01155(19) Uani 1.000000 .
C5 C -0.08789(10) 0.34807(9) 0.33369(8) 0.01157(19) Uani 1.000000 .
C6 C -0.22834(11) 0.30754(10) 0.37124(9) 0.0140(2) Uani 1.000000 .
H6 H -0.2214(11) 0.2088(11) 0.4106(10) 0.031(3) Uani 1.000000 .
C7 C -0.37439(11) 0.39085(10) 0.35494(9) 0.0160(2) Uani 1.000000 .
H7 H -0.4824(11) 0.3594(10) 0.3871(10) 0.030(3) Uani 1.000000 .
C8 C -0.38184(11) 0.51637(10) 0.29808(9) 0.0159(2) Uani 1.000000 .
H8 H -0.4937(12) 0.5842(11) 0.2871(11) 0.033(3) Uani 1.000000 .
C9 C -0.23933(10) 0.55161(9) 0.25448(9) 0.01449(19) Uani 1.000000 .
C10 C -0.08971(10) 0.47214(9) 0.27005(8) 0.01209(19) Uani 1.000000 .
C11 C 0.06069(12) 0.51845(11) 0.22438(11) 0.0149(2) Uani 1.000000 .
H11a H 0.1257(12) 0.4976(10) 0.1080(10) 0.027(3) Uani 1.000000 .
H11b H 0.0189(12) 0.6297(11) 0.2477(10) 0.034(3) Uani 1.000000 .
C12 C 0.18655(12) 0.44341(10) 0.28979(11) 0.0145(2) Uani 1.000000 .
H12a H 0.3025(11) 0.4604(10) 0.2348(9) 0.028(3) Uani 1.000000 .
H12b H 0.1390(12) 0.4838(10) 0.4016(10) 0.032(3) Uani 1.000000 .
C13 C 0.22248(11) 0.28572(9) 0.27642(10) 0.01223(19) Uani 1.000000 .
H13 H 0.2598(10) 0.2521(10) 0.1656(9) 0.023(3) Uani 1.000000 .
C20 C 0.52538(10) 0.15683(9) 0.22537(9) 0.01236(19) Uani 1.000000 .
C21 C 0.70698(10) 0.15966(10) -0.02026(8) 0.0139(2) Uani 1.000000 .
C22 C 0.75553(15) 0.00615(12) -0.06720(13) 0.0216(2) Uani 1.000000 .
H22a H 0.7747(13) -0.0567(12) 0.0106(11) 0.042(3) Uani 1.000000 .
H22b H 0.6550(13) -0.0053(12) -0.0907(11) 0.049(4) Uani 1.000000 .
H22c H 0.8676(14) -0.0266(11) -0.1607(11) 0.040(3) Uani 1.000000 .
C23 C 0.66590(15) 0.25097(14) -0.12958(12) 0.0223(2) Uani 1.000000 .
H23a H 0.5708(14) 0.2296(12) -0.1519(10) 0.044(3) Uani 1.000000 .
H23b H 0.6166(13) 0.3598(12) -0.0875(10) 0.042(3) Uani 1.000000 .
H23c H 0.7777(12) 0.2260(11) -0.2284(10) 0.041(3) Uani 1.000000 .
C24 C 0.84186(14) 0.18830(13) 0.01152(12) 0.0185(2) Uani 1.000000 .
H24a H 0.7965(12) 0.2978(12) 0.0530(10) 0.036(3) Uani 1.000000 .
H24b H 0.8739(12) 0.1250(12) 0.0892(10) 0.035(3) Uani 1.000000 .
H24c H 0.9512(12) 0.1665(11) -0.0838(11) 0.039(3) Uani 1.000000 .


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 C20 1.2220(11) . ?
O2 C20 1.3358(10) . ?
O2 C21 1.4777(9) . ?
O3 H3 0.980(13) . ?
O3 C2 1.4153(11) . ?
O4 N2 1.2190(9) . ?
O5 N2 1.2256(10) . ?
N1 C1 1.4538(11) . ?
N1 C13 1.4632(11) . ?
N1 C20 1.3608(10) . ?
N2 C9 1.4699(11) . ?
C1 H1a 1.088(10) . ?
C1 H1b 1.118(9) . ?
C1 C2 1.5235(13) . ?
C2 H2 1.113(9) . ?
C2 C3 1.5005(13) . ?
C3 H3a 1.089(8) . ?
C3 C4 1.3414(12) . ?
C4 C5 1.4831(12) . ?
C4 C13 1.5087(11) . ?
C5 C6 1.4036(11) . ?
C5 C10 1.4116(12) . ?
C6 H6 1.070(10) . ?
C6 C7 1.3878(13) . ?
C7 H7 1.078(8) . ?
C7 C8 1.3888(13) . ?
C8 H8 1.068(10) . ?
C8 C9 1.3845(12) . ?
C9 C10 1.4008(12) . ?
C10 C11 1.5174(12) . ?
C11 H11a 1.110(9) . ?
C11 H11b 1.072(10) . ?
C11 C12 1.5287(14) . ?
C12 H12a 1.071(8) . ?
C12 H12b 1.106(9) . ?
C12 C13 1.5336(12) . ?
C13 H13 1.094(8) . ?
C21 C22 1.5196(13) . ?
C21 C23 1.5211(14) . ?
C21 C24 1.5187(13) . ?
C22 H22a 1.045(12) . ?
C22 H22b 1.085(10) . ?
C22 H22c 1.062(10) . ?
C23 H23a 1.077(11) . ?
C23 H23b 1.082(11) . ?
C23 H23c 1.094(9) . ?
C24 H24a 1.090(11) . ?
C24 H24b 1.082(11) . ?
C24 H24c 1.064(9) . ?

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
C21 O2 C20 121.53(7) . . ?
C2 O3 H3 107.5(7) . . ?
C13 N1 C1 117.79(7) . . ?
C20 N1 C1 119.64(8) . . ?
C20 N1 C13 122.48(7) . . ?
O5 N2 O4 124.53(8) . . ?
C9 N2 O4 118.13(8) . . ?
C9 N2 O5 117.31(7) . . ?
H1a C1 N1 108.3(5) . . ?
H1b C1 N1 109.8(5) . . ?
H1b C1 H1a 107.8(7) . . ?
C2 C1 N1 109.60(8) . . ?
C2 C1 H1a 113.1(5) . . ?
C2 C1 H1b 108.2(4) . . ?
C1 C2 O3 111.40(8) . . ?
H2 C2 O3 111.0(4) . . ?
H2 C2 C1 108.7(4) . . ?
C3 C2 O3 106.87(7) . . ?
C3 C2 C1 108.63(8) . . ?
C3 C2 H2 110.2(5) . . ?
H3a C3 C2 116.2(5) . . ?
C4 C3 C2 123.28(8) . . ?
C4 C3 H3a 120.4(5) . . ?
C5 C4 C3 122.42(7) . . ?
C13 C4 C3 122.68(8) . . ?
C13 C4 C5 114.86(7) . . ?
C6 C5 C4 120.20(8) . . ?
C10 C5 C4 119.98(7) . . ?
C10 C5 C6 119.81(8) . . ?
H6 C6 C5 119.2(5) . . ?
C7 C6 C5 121.56(9) . . ?
C7 C6 H6 119.2(5) . . ?
H7 C7 C6 120.5(5) . . ?
C8 C7 C6 119.61(9) . . ?
C8 C7 H7 119.8(5) . . ?
H8 C8 C7 121.4(5) . . ?
C9 C8 C7 118.27(9) . . ?
C9 C8 H8 120.4(5) . . ?
C8 C9 N2 115.51(8) . . ?
C10 C9 N2 120.19(7) . . ?
C10 C9 C8 124.30(9) . . ?
C9 C10 C5 116.29(7) . . ?
C11 C10 C5 121.75(8) . . ?
C11 C10 C9 121.95(8) . . ?
H11a C11 C10 108.2(5) . . ?
H11b C11 C10 110.4(5) . . ?
H11b C11 H11a 105.2(7) . . ?
C12 C11 C10 113.01(8) . . ?
C12 C11 H11a 109.4(5) . . ?
C12 C11 H11b 110.3(6) . . ?
H12a C12 C11 109.3(5) . . ?
H12b C12 C11 111.7(5) . . ?
H12b C12 H12a 107.6(7) . . ?
C13 C12 C11 109.53(8) . . ?
C13 C12 H12a 108.8(5) . . ?
C13 C12 H12b 109.8(5) . . ?
C4 C13 N1 111.17(7) . . ?
C12 C13 N1 113.50(7) . . ?
C12 C13 C4 108.47(7) . . ?
H13 C13 N1 107.6(5) . . ?
H13 C13 C4 108.7(4) . . ?
H13 C13 C12 107.2(5) . . ?
O2 C20 O1 125.08(7) . . ?
N1 C20 O1 123.61(8) . . ?
N1 C20 O2 111.28(8) . . ?
C22 C21 O2 108.80(7) . . ?
C23 C21 O2 102.09(7) . . ?
C23 C21 C22 110.75(9) . . ?
C24 C21 O2 111.77(7) . . ?
C24 C21 C22 112.99(9) . . ?
C24 C21 C23 109.93(9) . . ?
H22a C22 C21 111.4(6) . . ?
H22b C22 C21 108.6(6) . . ?
H22b C22 H22a 109.7(8) . . ?
H22c C22 C21 109.6(5) . . ?
H22c C22 H22a 109.5(8) . . ?
H22c C22 H22b 108.0(7) . . ?
H23a C23 C21 109.4(6) . . ?
H23b C23 C21 108.9(6) . . ?
H23b C23 H23a 108.7(8) . . ?
H23c C23 C21 110.4(6) . . ?
H23c C23 H23a 107.0(7) . . ?
H23c C23 H23b 112.3(7) . . ?
H24a C24 C21 110.0(6) . . ?
H24b C24 C21 111.8(5) . . ?
H24b C24 H24a 107.6(8) . . ?
H24c C24 C21 108.3(5) . . ?
H24c C24 H24a 109.4(7) . . ?
H24c C24 H24b 109.8(8) . . ?

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 C20 O2 C21 8.80(11) . . . . ?
O1 C20 N1 C1 6.73(11) . . . . ?
O1 C20 N1 C13 -176.77(8) . . . . ?
O2 C20 N1 C1 -171.59(7) . . . . ?
O2 C20 N1 C13 4.92(9) . . . . ?
O3 C2 C1 N1 -169.04(8) . . . . ?
O3 C2 C3 C4 143.32(7) . . . . ?
O4 N2 C9 C8 -131.45(8) . . . . ?
O4 N2 C9 C10 48.40(9) . . . . ?
O5 N2 C9 C8 46.40(9) . . . . ?
O5 N2 C9 C10 -133.75(8) . . . . ?
N1 C1 C2 C3 -51.59(9) . . . . ?
N1 C13 C4 C3 -0.80(9) . . . . ?
N1 C13 C4 C5 176.92(7) . . . . ?
N1 C13 C12 C11 171.39(7) . . . . ?
N1 C20 O2 C21 -172.91(6) . . . . ?
N2 C9 C8 C7 176.61(8) . . . . ?
N2 C9 C10 C5 -179.29(8) . . . . ?
N2 C9 C10 C11 2.15(10) . . . . ?
C1 N1 C13 C4 -31.99(8) . . . . ?
C1 N1 C13 C12 90.61(8) . . . . ?
C1 C2 C3 C4 23.02(9) . . . . ?
C2 C1 N1 C13 59.97(9) . . . . ?
C2 C1 N1 C20 -123.36(8) . . . . ?
C2 C3 C4 C5 -173.92(8) . . . . ?
C2 C3 C4 C13 3.63(11) . . . . ?
C3 C4 C5 C6 -22.22(10) . . . . ?
C3 C4 C5 C10 156.89(9) . . . . ?
C3 C4 C13 C12 -126.26(9) . . . . ?
C4 C5 C6 C7 175.29(8) . . . . ?
C4 C5 C10 C9 -176.17(8) . . . . ?
C4 C5 C10 C11 2.39(10) . . . . ?
C4 C13 N1 C20 151.44(7) . . . . ?
C4 C13 C12 C11 -64.53(8) . . . . ?
C5 C4 C13 C12 51.46(8) . . . . ?
C5 C6 C7 C8 1.07(10) . . . . ?
C5 C10 C9 C8 0.55(9) . . . . ?
C5 C10 C11 C12 -16.05(9) . . . . ?
C6 C5 C4 C13 160.05(8) . . . . ?
C6 C5 C10 C9 2.95(9) . . . . ?
C6 C5 C10 C11 -178.50(8) . . . . ?
C6 C7 C8 C9 2.37(10) . . . . ?
C7 C6 C5 C10 -3.82(11) . . . . ?
C7 C8 C9 C10 -3.24(11) . . . . ?
C8 C9 C10 C11 -178.01(9) . . . . ?
C9 C10 C11 C12 162.42(9) . . . . ?
C10 C5 C4 C13 -20.83(9) . . . . ?
C10 C11 C12 C13 46.66(9) . . . . ?
C12 C13 N1 C20 -85.96(8) . . . . ?
C20 O2 C21 C22 66.38(9) . . . . ?
C20 O2 C21 C23 -176.51(9) . . . . ?
C20 O2 C21 C24 -59.08(8) . . . . ?


_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 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.761
####################################################################### 
# 
# 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_laiyt1cult_auto
_database_code_depnum_ccdc_archive 'CCDC 2300819'
loop_
_audit_author_name
_audit_author_address
'Shiqiang Ma'
;Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2026-04-20 downloaded from the CCDC.
;
_audit_creation_date             2022-08-18
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O5'
_chemical_formula_sum            'C21 H19 N O5'
_chemical_formula_weight         365.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C29H25NO5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   12.93147(12)
_cell_length_b                   14.11707(13)
_cell_length_c                   9.64407(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.7721(8)
_cell_angle_gamma                90
_cell_volume                     1759.73(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7546
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7040
_cell_measurement_theta_min      4.6200
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (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_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11298
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.918
_diffrn_reflns_theta_min         4.638
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00 131.00   1.00    3.00    --  112.00 -45.00 -30.00   91
  2  ω    -80.00 -11.00   1.00    1.50    --  -41.13 125.00-120.00   69
  3  ω    -85.00  -7.00   1.00    1.50    --  -41.13 125.00 120.00   78
  4  ω    -77.00 -12.00   1.00    1.50    --  -41.13 125.00 -30.00   65
  5  ω     29.00 110.00   1.00    1.50    --   41.13  37.00-150.00   81
  6  ω     27.00 105.00   1.00    1.50    --   41.13  57.00 120.00   78
  7  ω     87.00 175.00   1.00    3.00    --  112.00  30.00  90.00   88
  8  ω     29.00 107.00   1.00    3.00    --  112.00 -94.00 -30.00   78
  9  ω     36.00 108.00   1.00    3.00    --  112.00-111.00 -60.00   72
 10  ω     86.00 171.00   1.00    3.00    --  112.00  61.00 150.00   85
 11  ω    103.00 178.00   1.00    3.00    --  112.00  77.00   0.00   75
 12  ω    100.00 178.00   1.00    3.00    --  112.00  45.00 120.00   78
 13  ω     86.00 175.00   1.00    3.00    --  112.00  45.00-150.00   89
 14  ω     59.00 108.00   1.00    3.00    --  112.00-111.00 120.00   49
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0584651000
_diffrn_orient_matrix_UB_12      0.0864150000
_diffrn_orient_matrix_UB_13      0.0605147000
_diffrn_orient_matrix_UB_21      -0.1032083000
_diffrn_orient_matrix_UB_22      0.0432123000
_diffrn_orient_matrix_UB_23      0.0447244000
_diffrn_orient_matrix_UB_31      0.0117139000
_diffrn_orient_matrix_UB_32      -0.0508276000
_diffrn_orient_matrix_UB_33      0.1409108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3332
_reflns_number_total             3646
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.052
_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)+(0.0447P)²+0.5420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0885
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.34669(6) 0.34789(5) 0.21491(7) 0.01719(17) Uani 1 1 d . . . . .
O2 O 0.25740(6) 0.11865(5) 0.09324(7) 0.01909(18) Uani 1 1 d . . . . .
O3 O 0.17408(6) 0.03363(6) 0.25313(8) 0.02138(18) Uani 1 1 d . . . . .
O4 O 0.03671(7) -0.13643(7) -0.43674(8) 0.0291(2) Uani 1 1 d . . . . .
O5 O -0.02346(6) -0.23854(6) -0.29228(8) 0.02476(19) Uani 1 1 d . . . . .
N1 N 0.02496(7) -0.16608(7) -0.31924(9) 0.0195(2) Uani 1 1 d . . . . .
C1 C 0.30170(8) 0.28105(7) 0.11909(10) 0.0171(2) Uani 1 1 d . . . . .
H1 H 0.3496 0.2703 0.0412 0.021 Uiso 1 1 calc R U . . .
C2 C 0.28715(8) 0.18907(7) 0.19808(10) 0.0170(2) Uani 1 1 d . . . . .
H2 H 0.2302 0.1967 0.2650 0.020 Uiso 1 1 calc R U . . .
C3 C 0.38444(8) 0.16010(7) 0.27466(11) 0.0180(2) Uani 1 1 d . . . . .
H3 H 0.3921 0.0962 0.3043 0.022 Uiso 1 1 calc R U . . .
C4 C 0.46104(8) 0.22171(7) 0.30257(10) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.55532(8) 0.19738(8) 0.38721(11) 0.0180(2) Uani 1 1 d . . . . .
C6 C 0.58339(9) 0.10264(8) 0.41162(12) 0.0224(2) Uani 1 1 d . . . . .
H6 H 0.5441 0.0535 0.3682 0.027 Uiso 1 1 calc R U . . .
C7 C 0.66730(9) 0.07952(9) 0.49793(12) 0.0262(3) Uani 1 1 d . . . . .
H7 H 0.6853 0.0150 0.5129 0.031 Uiso 1 1 calc R U . . .
C8 C 0.72511(9) 0.15092(9) 0.56260(13) 0.0274(3) Uani 1 1 d . . . . .
H8 H 0.7821 0.1355 0.6229 0.033 Uiso 1 1 calc R U . . .
C9 C 0.69883(9) 0.24473(9) 0.53830(12) 0.0253(3) Uani 1 1 d . . . . .
H9 H 0.7382 0.2934 0.5829 0.030 Uiso 1 1 calc R U . . .
C10 C 0.61554(8) 0.26944(8) 0.44956(11) 0.0197(2) Uani 1 1 d . . . . .
C11 C 0.59325(8) 0.37277(8) 0.42145(12) 0.0217(2) Uani 1 1 d . . . . .
H11A H 0.6391 0.3955 0.3482 0.026 Uiso 1 1 calc R U . . .
H11B H 0.6093 0.4098 0.5066 0.026 Uiso 1 1 calc R U . . .
C12 C 0.48107(8) 0.39049(7) 0.37584(11) 0.0185(2) Uani 1 1 d . . . . .
H12A H 0.4355 0.3797 0.4549 0.022 Uiso 1 1 calc R U . . .
H12B H 0.4726 0.4571 0.3452 0.022 Uiso 1 1 calc R U . . .
C13 C 0.45049(8) 0.32405(7) 0.25722(10) 0.0162(2) Uani 1 1 d . . . . .
H13 H 0.4970 0.3356 0.1780 0.019 Uiso 1 1 calc R U . . .
C14 C 0.20061(8) 0.32122(8) 0.06278(11) 0.0209(2) Uani 1 1 d . . . . .
H14A H 0.1555 0.3355 0.1399 0.031 Uiso 1 1 calc R U . . .
H14B H 0.1667 0.2748 0.0010 0.031 Uiso 1 1 calc R U . . .
H14C H 0.2140 0.3794 0.0110 0.031 Uiso 1 1 calc R U . . .
C20 C 0.19627(8) 0.04773(7) 0.13450(11) 0.0161(2) Uani 1 1 d . . . . .
C21 C 0.15671(7) -0.00994(7) 0.01391(10) 0.0156(2) Uani 1 1 d . . . . .
C22 C 0.17968(8) 0.01424(8) -0.12195(11) 0.0195(2) Uani 1 1 d . . . . .
H22 H 0.2248 0.0657 -0.1392 0.023 Uiso 1 1 calc R U . . .
C23 C 0.13634(8) -0.03713(8) -0.23182(11) 0.0208(2) Uani 1 1 d . . . . .
H23 H 0.1506 -0.0212 -0.3250 0.025 Uiso 1 1 calc R U . . .
C24 C 0.07175(8) -0.11213(7) -0.20199(11) 0.0172(2) Uani 1 1 d . . . . .
C25 C 0.04932(8) -0.13912(7) -0.06821(11) 0.0173(2) Uani 1 1 d . . . . .
H25 H 0.0059 -0.1919 -0.0516 0.021 Uiso 1 1 calc R U . . .
C26 C 0.09225(8) -0.08659(7) 0.04092(11) 0.0167(2) Uani 1 1 d . . . . .
H26 H 0.0777 -0.1028 0.1339 0.020 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 1.4316(12) . ?
O1 C13 1.4309(12) . ?
O2 C2 1.4610(12) . ?
O2 C20 1.3435(12) . ?
O3 C20 1.2046(13) . ?
O4 N1 1.2219(13) . ?
O5 N1 1.2313(12) . ?
N1 C24 1.4773(13) . ?
C1 H1 1.0000 . ?
C1 C2 1.5202(14) . ?
C1 C14 1.5104(15) . ?
C2 H2 1.0000 . ?
C2 C3 1.4960(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3393(15) . ?
C4 C5 1.4864(15) . ?
C4 C13 1.5144(14) . ?
C5 C6 1.4037(15) . ?
C5 C10 1.4048(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3860(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3910(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3854(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3990(16) . ?
C10 C11 1.5099(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5235(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5221(14) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C20 C21 1.4968(14) . ?
C21 C22 1.3948(14) . ?
C21 C26 1.3954(14) . ?
C22 H22 0.9500 . ?
C22 C23 1.3877(15) . ?
C23 H23 0.9500 . ?
C23 C24 1.3844(15) . ?
C24 C25 1.3846(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.3891(15) . ?
C26 H26 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
C13 O1 C1 112.83(8) . . ?
C20 O2 C2 116.54(8) . . ?
O4 N1 O5 123.99(9) . . ?
O4 N1 C24 118.26(9) . . ?
O5 N1 C24 117.75(9) . . ?
O1 C1 H1 109.6 . . ?
O1 C1 C2 107.07(8) . . ?
O1 C1 C14 108.34(8) . . ?
C2 C1 H1 109.6 . . ?
C14 C1 H1 109.6 . . ?
C14 C1 C2 112.44(9) . . ?
O2 C2 C1 105.57(8) . . ?
O2 C2 H2 109.6 . . ?
O2 C2 C3 110.80(8) . . ?
C1 C2 H2 109.6 . . ?
C3 C2 C1 111.45(9) . . ?
C3 C2 H2 109.6 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.82(10) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 123.32(10) . . ?
C3 C4 C13 120.13(9) . . ?
C5 C4 C13 116.36(9) . . ?
C6 C5 C4 121.04(10) . . ?
C6 C5 C10 118.76(10) . . ?
C10 C5 C4 120.14(10) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.24(11) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 119.91(11) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.42(11) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.46(11) . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C11 121.50(10) . . ?
C9 C10 C5 119.17(10) . . ?
C9 C10 C11 119.32(10) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.66(9) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 C11 109.80(9) . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
O1 C13 C4 112.46(8) . . ?
O1 C13 C12 106.80(8) . . ?
O1 C13 H13 109.0 . . ?
C4 C13 C12 110.60(8) . . ?
C4 C13 H13 109.0 . . ?
C12 C13 H13 109.0 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C20 C21 111.42(8) . . ?
O3 C20 O2 124.33(9) . . ?
O3 C20 C21 124.22(9) . . ?
C22 C21 C20 121.28(9) . . ?
C22 C21 C26 120.73(9) . . ?
C26 C21 C20 117.94(9) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.78(10) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.9 . . ?
C24 C23 C22 118.23(10) . . ?
C24 C23 H23 120.9 . . ?
C23 C24 N1 118.08(9) . . ?
C23 C24 C25 123.31(10) . . ?
C25 C24 N1 118.61(9) . . ?
C24 C25 H25 121.0 . . ?
C24 C25 C26 117.96(9) . . ?
C26 C25 H25 121.0 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 119.97(10) . . ?
C25 C26 H26 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -170.97(7) . . . . ?
O1 C1 C2 C3 -50.60(11) . . . . ?
O2 C2 C3 C4 135.97(10) . . . . ?
O2 C20 C21 C22 -2.91(14) . . . . ?
O2 C20 C21 C26 179.78(9) . . . . ?
O3 C20 C21 C22 175.45(10) . . . . ?
O3 C20 C21 C26 -1.86(15) . . . . ?
O4 N1 C24 C23 -7.33(15) . . . . ?
O4 N1 C24 C25 172.92(10) . . . . ?
O5 N1 C24 C23 172.52(10) . . . . ?
O5 N1 C24 C25 -7.23(14) . . . . ?
N1 C24 C25 C26 -178.77(9) . . . . ?
C1 O1 C13 C4 -48.94(11) . . . . ?
C1 O1 C13 C12 -170.45(8) . . . . ?
C1 C2 C3 C4 18.73(13) . . . . ?
C2 O2 C20 O3 -8.02(15) . . . . ?
C2 O2 C20 C21 170.34(8) . . . . ?
C2 C3 C4 C5 175.35(9) . . . . ?
C2 C3 C4 C13 0.37(15) . . . . ?
C3 C4 C5 C6 17.57(15) . . . . ?
C3 C4 C5 C10 -159.56(10) . . . . ?
C3 C4 C13 O1 13.29(13) . . . . ?
C3 C4 C13 C12 132.60(10) . . . . ?
C4 C5 C6 C7 -175.68(10) . . . . ?
C4 C5 C10 C9 174.61(9) . . . . ?
C4 C5 C10 C11 -6.22(15) . . . . ?
C5 C4 C13 O1 -162.02(8) . . . . ?
C5 C4 C13 C12 -42.71(12) . . . . ?
C5 C6 C7 C8 0.26(17) . . . . ?
C5 C10 C11 C12 24.46(14) . . . . ?
C6 C5 C10 C9 -2.59(15) . . . . ?
C6 C5 C10 C11 176.58(10) . . . . ?
C6 C7 C8 C9 -0.89(18) . . . . ?
C7 C8 C9 C10 -0.26(18) . . . . ?
C8 C9 C10 C5 2.02(17) . . . . ?
C8 C9 C10 C11 -177.17(10) . . . . ?
C9 C10 C11 C12 -156.37(10) . . . . ?
C10 C5 C6 C7 1.49(16) . . . . ?
C10 C11 C12 C13 -50.93(12) . . . . ?
C11 C12 C13 O1 -176.98(8) . . . . ?
C11 C12 C13 C4 60.35(11) . . . . ?
C13 O1 C1 C2 68.12(10) . . . . ?
C13 O1 C1 C14 -170.37(8) . . . . ?
C13 C4 C5 C6 -167.28(9) . . . . ?
C13 C4 C5 C10 15.59(14) . . . . ?
C14 C1 C2 O2 70.15(10) . . . . ?
C14 C1 C2 C3 -169.48(9) . . . . ?
C20 O2 C2 C1 -150.24(9) . . . . ?
C20 O2 C2 C3 88.97(10) . . . . ?
C20 C21 C22 C23 -175.87(10) . . . . ?
C20 C21 C26 C25 176.64(9) . . . . ?
C21 C22 C23 C24 -0.61(16) . . . . ?
C22 C21 C26 C25 -0.68(15) . . . . ?
C22 C23 C24 N1 179.43(9) . . . . ?
C22 C23 C24 C25 -0.84(17) . . . . ?
C23 C24 C25 C26 1.51(16) . . . . ?
C24 C25 C26 C21 -0.71(15) . . . . ?
C26 C21 C22 C23 1.36(16) . . . . ?

_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.778
