# Supplementary Information (SI) for RSC Advances.
# 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. 
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data_111
_database_code_depnum_ccdc_archive 'CCDC 2526401'
loop_
_audit_author_name
_audit_author_address
'Zhipeng Wang'
;Hebei North university
China
;
_audit_update_record             
;
2026-04-11 deposited with the CCDC.	2026-05-07 downloaded from the CCDC.
;
_audit_creation_date             2025-11-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 O7, 1.5(C10 H8 N2)'
_chemical_formula_sum            'C31 H24 N3 O7'
_chemical_formula_weight         550.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4152(5)
_cell_length_b                   11.1869(6)
_cell_length_c                   13.2359(7)
_cell_angle_alpha                80.211(4)
_cell_angle_beta                 89.105(4)
_cell_angle_gamma                77.040(4)
_cell_volume                     1338.44(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3878
_cell_measurement_temperature    295
_cell_measurement_theta_max      66.160
_cell_measurement_theta_min      3.389
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1385 before and 0.0900 after correction.
The Ratio of minimum to maximum transmission is 0.5239.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             574
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16419
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.608
_diffrn_reflns_theta_max         66.608
_diffrn_reflns_theta_min         3.389
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3240
_reflns_number_total             4737
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.022
_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)+(0.0963P)²+0.1691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1788
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6A), C8(H8), C11(H11), C12(H12), C15(H15), C2L(H2L), C3L(H3L), C4L(H4L),
 C5L(H5L), C7L(H7L), C8L(H8L), C9L(H9L), C10L(H10L), C12L(H12L), C13L(H13L),
 C14L(H14L), C15L(H15L)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O5(H5), O6(H6)
;
_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 0.44368(16) 0.15977(15) 0.49204(11) 0.0446(4) Uani 1 1 d . . . . .
O2 O 0.14737(19) 0.03508(19) 0.60929(12) 0.0589(5) Uani 1 1 d . . . . .
H2 H 0.081884 0.014858 0.580789 0.088 Uiso 1 1 calc R U . . .
O3 O 0.11894(19) 0.00910(18) 0.41086(13) 0.0580(5) Uani 1 1 d . . . . .
O4 O 0.2016(2) 0.04681(19) 0.21870(13) 0.0603(5) Uani 1 1 d . . . . .
H4 H 0.160072 0.015511 0.267686 0.090 Uiso 1 1 calc R U . . .
O5 O 0.5943(2) 0.2417(2) 0.15116(13) 0.0641(5) Uani 1 1 d . . . . .
H5 H 0.644815 0.278814 0.178355 0.096 Uiso 1 1 calc R U . . .
O6 O 0.4813(2) 0.2483(2) 0.94063(13) 0.0641(5) Uani 1 1 d . . . . .
H6 H 0.549965 0.282705 0.935550 0.096 Uiso 1 1 calc R U . . .
O7 O 0.2778(2) 0.12477(19) 0.93571(13) 0.0622(5) Uani 1 1 d . . . . .
C1 C 0.3495(2) 0.1243(2) 0.56465(16) 0.0392(5) Uani 1 1 d . . . . .
C2 C 0.2408(2) 0.0724(2) 0.53820(16) 0.0418(5) Uani 1 1 d . . . . .
C3 C 0.2210(2) 0.0562(2) 0.43369(17) 0.0434(5) Uani 1 1 d . . . . .
C4 C 0.3181(2) 0.0991(2) 0.36009(16) 0.0412(5) Uani 1 1 d . . . . .
C5 C 0.3069(2) 0.0957(2) 0.25308(17) 0.0462(5) Uani 1 1 d . . . . .
C6 C 0.3994(3) 0.1437(2) 0.18553(18) 0.0497(6) Uani 1 1 d . . . . .
H6A H 0.390451 0.142131 0.115916 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5076(3) 0.1952(2) 0.22112(18) 0.0492(5) Uani 1 1 d . . . . .
C8 C 0.5228(2) 0.1996(2) 0.32496(17) 0.0465(5) Uani 1 1 d . . . . .
H8 H 0.594794 0.233648 0.348563 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4276(2) 0.1518(2) 0.39122(16) 0.0410(5) Uani 1 1 d . . . . .
C10 C 0.3854(2) 0.1521(2) 0.66447(16) 0.0398(5) Uani 1 1 d . . . . .
C11 C 0.4960(2) 0.2150(2) 0.66965(17) 0.0476(5) Uani 1 1 d . . . . .
H11 H 0.547574 0.235698 0.611222 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5299(3) 0.2471(2) 0.76187(18) 0.0508(6) Uani 1 1 d . . . . .
H12 H 0.603717 0.289610 0.764456 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4556(2) 0.2167(2) 0.84936(17) 0.0468(5) Uani 1 1 d . . . . .
C14 C 0.3462(2) 0.1509(2) 0.84503(17) 0.0454(5) Uani 1 1 d . . . . .
C15 C 0.3114(2) 0.1193(2) 0.75411(17) 0.0433(5) Uani 1 1 d . . . . .
H15 H 0.238250 0.075978 0.752009 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2020(4) 0.0297(3) 0.9470(2) 0.0831(10) Uani 1 1 d . . . . .
H16A H 0.116399 0.055375 0.903204 0.125 Uiso 1 1 calc R U . . .
H16B H 0.173963 0.012141 1.017029 0.125 Uiso 1 1 calc R U . . .
H16C H 0.263388 -0.043805 0.928446 0.125 Uiso 1 1 calc R U . . .
N1L N 0.7774(3) 0.3574(2) 0.23036(19) 0.0670(6) Uani 1 1 d . . . . .
N2L N 1.2810(3) 0.6221(3) 0.4620(3) 0.0937(9) Uani 1 1 d . . . . .
C1L C 0.9750(3) 0.4713(2) 0.3140(2) 0.0589(6) Uani 1 1 d . . . . .
C2L C 1.0149(4) 0.3559(4) 0.2856(4) 0.1134(16) Uani 1 1 d . . . . .
H2L H 1.111480 0.312047 0.293816 0.136 Uiso 1 1 calc R U . . .
C3L C 0.9143(5) 0.3049(4) 0.2454(4) 0.1150(17) Uani 1 1 d . . . . .
H3L H 0.946682 0.226591 0.227487 0.138 Uiso 1 1 calc R U . . .
C4L C 0.7396(4) 0.4692(3) 0.2521(4) 0.0938(12) Uani 1 1 d . . . . .
H4L H 0.643195 0.511935 0.239240 0.113 Uiso 1 1 calc R U . . .
C5L C 0.8324(4) 0.5283(3) 0.2928(4) 0.0930(12) Uani 1 1 d . . . . .
H5L H 0.797362 0.608577 0.306064 0.112 Uiso 1 1 calc R U . . .
C6L C 1.0795(3) 0.5255(3) 0.3627(2) 0.0625(7) Uani 1 1 d . . . . .
C7L C 1.0484(4) 0.6443(3) 0.3840(3) 0.0881(11) Uani 1 1 d . . . . .
H7L H 0.957613 0.696405 0.365366 0.106 Uiso 1 1 calc R U . . .
C8L C 1.1499(4) 0.6869(4) 0.4325(4) 0.0979(12) Uani 1 1 d . . . . .
H8L H 1.123707 0.768030 0.445407 0.117 Uiso 1 1 calc R U . . .
C9L C 1.3112(4) 0.5088(4) 0.4418(5) 0.1225(18) Uani 1 1 d . . . . .
H9L H 1.402489 0.458833 0.462241 0.147 Uiso 1 1 calc R U . . .
C10L C 1.2181(4) 0.4586(4) 0.3927(4) 0.1123(16) Uani 1 1 d . . . . .
H10L H 1.248858 0.377903 0.379337 0.135 Uiso 1 1 calc R U . . .
N3L N 0.7047(3) 0.3772(3) 0.9318(2) 0.0723(7) Uani 1 1 d . . . . .
C11L C 0.9388(3) 0.4747(2) 0.9848(2) 0.0534(6) Uani 1 1 d . . . . .
C12L C 0.9571(4) 0.3535(3) 0.9688(4) 0.0899(12) Uani 1 1 d . . . . .
H12L H 1.049229 0.300629 0.975655 0.108 Uiso 1 1 calc R U . . .
C13L C 0.8386(4) 0.3111(4) 0.9426(4) 0.0972(12) Uani 1 1 d . . . . .
H13L H 0.855086 0.229164 0.931777 0.117 Uiso 1 1 calc R U . . .
C14L C 0.6872(3) 0.4948(3) 0.9448(3) 0.0738(8) Uani 1 1 d . . . . .
H14L H 0.594052 0.545808 0.935069 0.089 Uiso 1 1 calc R U . . .
C15L C 0.7978(3) 0.5456(3) 0.9715(2) 0.0664(7) Uani 1 1 d . . . . .
H15L H 0.777924 0.628195 0.980802 0.080 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 1.367(3) . ?
O1 C9 1.366(3) . ?
O2 H2 0.8200 . ?
O2 C2 1.356(3) . ?
O3 C3 1.258(3) . ?
O4 H4 0.8200 . ?
O4 C5 1.353(3) . ?
O5 H5 0.8200 . ?
O5 C7 1.341(3) . ?
O6 H6 0.8200 . ?
O6 C13 1.355(3) . ?
O7 C14 1.372(3) . ?
O7 C16 1.395(3) . ?
C1 C2 1.362(3) . ?
C1 C10 1.468(3) . ?
C2 C3 1.445(3) . ?
C3 C4 1.423(3) . ?
C4 C5 1.429(3) . ?
C4 C9 1.396(3) . ?
C5 C6 1.366(3) . ?
C6 H6A 0.9300 . ?
C6 C7 1.401(3) . ?
C7 C8 1.394(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(3) . ?
C10 C11 1.390(3) . ?
C10 C15 1.403(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C13 C14 1.401(3) . ?
C14 C15 1.375(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1L C3L 1.294(5) . ?
N1L C4L 1.300(4) . ?
N2L C8L 1.312(5) . ?
N2L C9L 1.307(5) . ?
C1L C2L 1.375(5) . ?
C1L C5L 1.362(4) . ?
C1L C6L 1.473(4) . ?
C2L H2L 0.9300 . ?
C2L C3L 1.366(5) . ?
C3L H3L 0.9300 . ?
C4L H4L 0.9300 . ?
C4L C5L 1.373(5) . ?
C5L H5L 0.9300 . ?
C6L C7L 1.371(4) . ?
C6L C10L 1.378(5) . ?
C7L H7L 0.9300 . ?
C7L C8L 1.371(5) . ?
C8L H8L 0.9300 . ?
C9L H9L 0.9300 . ?
C9L C10L 1.367(6) . ?
C10L H10L 0.9300 . ?
N3L C13L 1.307(5) . ?
N3L C14L 1.329(4) . ?
C11L C11L 1.481(5) 2_767 ?
C11L C12L 1.380(4) . ?
C11L C15L 1.382(4) . ?
C12L H12L 0.9300 . ?
C12L C13L 1.377(5) . ?
C13L H13L 0.9300 . ?
C14L H14L 0.9300 . ?
C14L C15L 1.371(4) . ?
C15L H15L 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 122.01(16) . . ?
C2 O2 H2 109.5 . . ?
C5 O4 H4 109.5 . . ?
C7 O5 H5 109.5 . . ?
C13 O6 H6 109.5 . . ?
C14 O7 C16 118.43(19) . . ?
O1 C1 C10 110.53(16) . . ?
C2 C1 O1 119.83(18) . . ?
C2 C1 C10 129.63(19) . . ?
O2 C2 C1 120.79(18) . . ?
O2 C2 C3 118.14(18) . . ?
C1 C2 C3 121.1(2) . . ?
O3 C3 C2 120.0(2) . . ?
O3 C3 C4 122.99(19) . . ?
C4 C3 C2 117.02(18) . . ?
C3 C4 C5 123.4(2) . . ?
C9 C4 C3 119.61(19) . . ?
C9 C4 C5 117.0(2) . . ?
O4 C5 C4 119.3(2) . . ?
O4 C5 C6 120.07(19) . . ?
C6 C5 C4 120.6(2) . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C7 C6 H6A 120.0 . . ?
O5 C7 C6 117.3(2) . . ?
O5 C7 C8 121.4(2) . . ?
C8 C7 C6 121.2(2) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 C7 117.6(2) . . ?
C9 C8 H8 121.2 . . ?
O1 C9 C4 120.32(19) . . ?
O1 C9 C8 116.07(18) . . ?
C8 C9 C4 123.61(19) . . ?
C11 C10 C1 118.38(19) . . ?
C11 C10 C15 118.87(19) . . ?
C15 C10 C1 122.75(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
O6 C13 C12 123.4(2) . . ?
O6 C13 C14 117.4(2) . . ?
C12 C13 C14 119.15(19) . . ?
O7 C14 C13 115.18(19) . . ?
O7 C14 C15 124.33(19) . . ?
C15 C14 C13 120.5(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.43(19) . . ?
C14 C15 H15 119.8 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3L N1L C4L 114.9(3) . . ?
C9L N2L C8L 114.6(3) . . ?
C2L C1L C6L 122.0(3) . . ?
C5L C1L C2L 113.7(3) . . ?
C5L C1L C6L 124.3(3) . . ?
C1L C2L H2L 119.6 . . ?
C3L C2L C1L 120.9(3) . . ?
C3L C2L H2L 119.6 . . ?
N1L C3L C2L 124.9(4) . . ?
N1L C3L H3L 117.6 . . ?
C2L C3L H3L 117.6 . . ?
N1L C4L H4L 117.8 . . ?
N1L C4L C5L 124.5(3) . . ?
C5L C4L H4L 117.8 . . ?
C1L C5L C4L 121.0(3) . . ?
C1L C5L H5L 119.5 . . ?
C4L C5L H5L 119.5 . . ?
C7L C6L C1L 124.0(3) . . ?
C7L C6L C10L 114.0(3) . . ?
C10L C6L C1L 122.0(3) . . ?
C6L C7L H7L 119.7 . . ?
C8L C7L C6L 120.6(3) . . ?
C8L C7L H7L 119.7 . . ?
N2L C8L C7L 125.0(4) . . ?
N2L C8L H8L 117.5 . . ?
C7L C8L H8L 117.5 . . ?
N2L C9L H9L 117.7 . . ?
N2L C9L C10L 124.7(4) . . ?
C10L C9L H9L 117.7 . . ?
C6L C10L H10L 119.5 . . ?
C9L C10L C6L 121.1(4) . . ?
C9L C10L H10L 119.5 . . ?
C13L N3L C14L 115.4(3) . . ?
C12L C11L C11L 122.5(3) . 2_767 ?
C12L C11L C15L 115.3(3) . . ?
C15L C11L C11L 122.1(3) . 2_767 ?
C11L C12L H12L 120.1 . . ?
C13L C12L C11L 119.9(3) . . ?
C13L C12L H12L 120.1 . . ?
N3L C13L C12L 125.0(3) . . ?
N3L C13L H13L 117.5 . . ?
C12L C13L H13L 117.5 . . ?
N3L C14L H14L 118.0 . . ?
N3L C14L C15L 124.0(3) . . ?
C15L C14L H14L 118.0 . . ?
C11L C15L H15L 119.8 . . ?
C14L C15L C11L 120.4(3) . . ?
C14L C15L H15L 119.8 . . ?

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 C1 C2 O2 179.1(2) . . . . ?
O1 C1 C2 C3 -1.3(3) . . . . ?
O1 C1 C10 C11 4.5(3) . . . . ?
O1 C1 C10 C15 -176.5(2) . . . . ?
O2 C2 C3 O3 0.3(3) . . . . ?
O2 C2 C3 C4 178.4(2) . . . . ?
O3 C3 C4 C5 1.6(4) . . . . ?
O3 C3 C4 C9 179.2(2) . . . . ?
O4 C5 C6 C7 179.5(2) . . . . ?
O5 C7 C8 C9 178.8(2) . . . . ?
O6 C13 C14 O7 -0.6(3) . . . . ?
O6 C13 C14 C15 178.0(2) . . . . ?
O7 C14 C15 C10 178.7(2) . . . . ?
C1 O1 C9 C4 -4.1(3) . . . . ?
C1 O1 C9 C8 175.03(19) . . . . ?
C1 C2 C3 O3 -179.3(2) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C10 C11 C12 177.7(2) . . . . ?
C1 C10 C15 C14 -178.0(2) . . . . ?
C2 C1 C10 C11 -174.9(2) . . . . ?
C2 C1 C10 C15 4.1(4) . . . . ?
C2 C3 C4 C5 -176.4(2) . . . . ?
C2 C3 C4 C9 1.1(3) . . . . ?
C3 C4 C5 O4 -1.7(4) . . . . ?
C3 C4 C5 C6 176.9(2) . . . . ?
C3 C4 C9 O1 1.4(3) . . . . ?
C3 C4 C9 C8 -177.6(2) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C5 C4 C9 O1 179.12(19) . . . . ?
C5 C4 C9 C8 0.1(3) . . . . ?
C5 C6 C7 O5 -179.5(2) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 O1 -178.8(2) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C9 O1 C1 C2 4.0(3) . . . . ?
C9 O1 C1 C10 -175.47(18) . . . . ?
C9 C4 C5 O4 -179.3(2) . . . . ?
C9 C4 C5 C6 -0.7(3) . . . . ?
C10 C1 C2 O2 -1.5(4) . . . . ?
C10 C1 C2 C3 178.0(2) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C10 C15 C14 1.1(3) . . . . ?
C11 C12 C13 O6 -178.3(2) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 O7 -179.9(2) . . . . ?
C12 C13 C14 C15 -1.4(4) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C15 C10 C11 C12 -1.4(4) . . . . ?
C16 O7 C14 C13 -160.6(3) . . . . ?
C16 O7 C14 C15 20.8(4) . . . . ?
N1L C4L C5L C1L -0.2(8) . . . . ?
N2L C9L C10L C6L -1.9(10) . . . . ?
C1L C2L C3L N1L 0.1(9) . . . . ?
C1L C6L C7L C8L 177.9(4) . . . . ?
C1L C6L C10L C9L -177.1(5) . . . . ?
C2L C1L C5L C4L 3.4(6) . . . . ?
C2L C1L C6L C7L 174.0(4) . . . . ?
C2L C1L C6L C10L -7.2(6) . . . . ?
C3L N1L C4L C5L -3.1(7) . . . . ?
C4L N1L C3L C2L 3.2(8) . . . . ?
C5L C1L C2L C3L -3.4(7) . . . . ?
C5L C1L C6L C7L -6.1(5) . . . . ?
C5L C1L C6L C10L 172.7(4) . . . . ?
C6L C1L C2L C3L 176.6(4) . . . . ?
C6L C1L C5L C4L -176.5(4) . . . . ?
C6L C7L C8L N2L 0.1(7) . . . . ?
C7L C6L C10L C9L 1.8(7) . . . . ?
C8L N2L C9L C10L 0.9(8) . . . . ?
C9L N2L C8L C7L -0.1(7) . . . . ?
C10L C6L C7L C8L -1.0(6) . . . . ?
N3L C14L C15L C11L 1.4(5) . . . . ?
C11L C11L C12L C13L 178.7(4) 2_767 . . . ?
C11L C11L C15L C14L -179.0(3) 2_767 . . . ?
C11L C12L C13L N3L -0.6(7) . . . . ?
C12L C11L C15L C14L 0.3(5) . . . . ?
C13L N3L C14L C15L -2.5(5) . . . . ?
C14L N3L C13L C12L 2.1(6) . . . . ?
C15L C11L C12L C13L -0.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2526402'
loop_
_audit_author_name
_audit_author_address
'Zhipeng Wang'
;Hebei North university
China
;
_audit_update_record             
;
2026-04-11 deposited with the CCDC.	2026-05-07 downloaded from the CCDC.
;
_audit_creation_date             2025-11-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Isoliquiritigenin-4,4'-Bipyridine
_chemical_formula_moiety         'C15 H12 O4, C10 H8 N2'
_chemical_formula_sum            'C25 H20 N2 O4'
_chemical_formula_weight         412.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   16.9971(3)
_cell_length_b                   9.4839(2)
_cell_length_c                   12.8861(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.2310(10)
_cell_angle_gamma                90
_cell_volume                     2060.70(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5138
_cell_measurement_temperature    295
_cell_measurement_theta_max      66.698
_cell_measurement_theta_min      2.620
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1203 before and 0.0772 after correction.
The Ratio of minimum to maximum transmission is 0.6498.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15643
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.047
_diffrn_reflns_theta_max         67.047
_diffrn_reflns_theta_min         2.620
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2815
_reflns_number_total             3638
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.033
_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)+(0.0941P)²+0.3821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1720
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4A), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C1L(H1L), C2L(H2L), C4L(H4L), C5L(H5L), C7L(H7L), C8L(H8L), C9L(H9L),
  C10L(H10L)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.87654(12) 0.5754(2) 0.92852(14) 0.0807(6) Uani 1 1 d . . . . .
H1 H 0.839193 0.536654 0.893193 0.121 Uiso 1 1 calc R U . . .
O2 O 1.06222(10) 0.9453(2) 0.90673(13) 0.0731(5) Uani 1 1 d . . . . .
H2 H 1.076305 0.920331 0.967135 0.110 Uiso 1 1 calc R U . . .
O3 O 0.77637(10) 0.52755(17) 0.76985(13) 0.0674(5) Uani 1 1 d . . . . .
O4 O 0.51939(11) 0.77774(18) 0.19681(13) 0.0709(5) Uani 1 1 d . . . . .
H4 H 0.485352 0.720032 0.175009 0.106 Uiso 1 1 calc R U . . .
C1 C 0.90546(13) 0.6794(2) 0.87164(16) 0.0556(5) Uani 1 1 d . . . . .
C2 C 0.96960(13) 0.7572(3) 0.91870(17) 0.0600(6) Uani 1 1 d . . . . .
H2A H 0.991629 0.735993 0.986660 0.072 Uiso 1 1 calc R U . . .
C3 C 1.00073(13) 0.8654(3) 0.86532(17) 0.0569(6) Uani 1 1 d . . . . .
C4 C 0.96833(13) 0.8962(3) 0.76251(17) 0.0579(6) Uani 1 1 d . . . . .
H4A H 0.989644 0.968172 0.725696 0.070 Uiso 1 1 calc R U . . .
C5 C 0.90549(12) 0.8202(3) 0.71690(16) 0.0551(5) Uani 1 1 d . . . . .
H5 H 0.884563 0.841774 0.648553 0.066 Uiso 1 1 calc R U . . .
C6 C 0.87077(12) 0.7104(2) 0.76876(15) 0.0500(5) Uani 1 1 d . . . . .
C7 C 0.80123(13) 0.6320(2) 0.72253(16) 0.0536(5) Uani 1 1 d . . . . .
C8 C 0.75756(13) 0.6778(3) 0.62344(16) 0.0572(5) Uani 1 1 d . . . . .
H8 H 0.776486 0.755249 0.589890 0.069 Uiso 1 1 calc R U . . .
C9 C 0.69181(12) 0.6142(2) 0.57845(16) 0.0529(5) Uani 1 1 d . . . . .
H9 H 0.674291 0.535838 0.612367 0.064 Uiso 1 1 calc R U . . .
C10 C 0.64530(12) 0.6569(2) 0.48117(16) 0.0482(5) Uani 1 1 d . . . . .
C11 C 0.66097(13) 0.7816(2) 0.42887(17) 0.0557(5) Uani 1 1 d . . . . .
H11 H 0.701202 0.840893 0.458567 0.067 Uiso 1 1 calc R U . . .
C12 C 0.61868(13) 0.8182(2) 0.33545(17) 0.0563(5) Uani 1 1 d . . . . .
H12 H 0.630577 0.901553 0.302774 0.068 Uiso 1 1 calc R U . . .
C13 C 0.55823(12) 0.7324(2) 0.28887(16) 0.0515(5) Uani 1 1 d . . . . .
C14 C 0.54081(12) 0.6085(2) 0.33874(17) 0.0534(5) Uani 1 1 d . . . . .
H14 H 0.500211 0.550142 0.308741 0.064 Uiso 1 1 calc R U . . .
C15 C 0.58398(12) 0.5722(2) 0.43309(17) 0.0527(5) Uani 1 1 d . . . . .
H15 H 0.571833 0.488810 0.465586 0.063 Uiso 1 1 calc R U . . .
N1L N 0.40100(12) 0.6596(2) 0.06843(15) 0.0624(5) Uani 1 1 d . . . . .
N2L N 0.13654(10) 0.6106(2) -0.39993(14) 0.0581(5) Uani 1 1 d . . . . .
C1L C 0.32287(15) 0.6663(3) 0.06991(18) 0.0638(6) Uani 1 1 d . . . . .
H1L H 0.303911 0.679445 0.133840 0.077 Uiso 1 1 calc R U . . .
C2L C 0.26882(14) 0.6547(2) -0.01880(17) 0.0581(6) Uani 1 1 d . . . . .
H2L H 0.214830 0.662014 -0.014049 0.070 Uiso 1 1 calc R U . . .
C3L C 0.29475(12) 0.6322(2) -0.11461(16) 0.0476(5) Uani 1 1 d . . . . .
C4L C 0.37633(13) 0.6228(3) -0.11596(18) 0.0600(6) Uani 1 1 d . . . . .
H4L H 0.396955 0.605661 -0.178276 0.072 Uiso 1 1 calc R U . . .
C5L C 0.42605(14) 0.6392(3) -0.02400(19) 0.0652(6) Uani 1 1 d . . . . .
H5L H 0.480445 0.635681 -0.026655 0.078 Uiso 1 1 calc R U . . .
C6L C 0.23893(11) 0.6216(2) -0.21253(15) 0.0464(5) Uani 1 1 d . . . . .
C7L C 0.17451(13) 0.7121(2) -0.23179(18) 0.0578(6) Uani 1 1 d . . . . .
H7L H 0.164232 0.778067 -0.181849 0.069 Uiso 1 1 calc R U . . .
C8L C 0.12631(13) 0.7031(3) -0.32498(19) 0.0630(6) Uani 1 1 d . . . . .
H8L H 0.083854 0.765427 -0.336705 0.076 Uiso 1 1 calc R U . . .
C9L C 0.19743(12) 0.5220(2) -0.38028(16) 0.0555(5) Uani 1 1 d . . . . .
H9L H 0.205078 0.454872 -0.430643 0.067 Uiso 1 1 calc R U . . .
C10L C 0.24992(12) 0.5245(2) -0.28905(16) 0.0512(5) Uani 1 1 d . . . . .
H10L H 0.292105 0.461409 -0.279452 0.061 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 H1 0.8200 . ?
O1 C1 1.358(3) . ?
O2 H2 0.8200 . ?
O2 C3 1.346(3) . ?
O3 C7 1.263(3) . ?
O4 H4 0.8200 . ?
O4 C13 1.353(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.412(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.378(3) . ?
C3 C4 1.400(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.359(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.407(3) . ?
C6 C7 1.459(3) . ?
C7 C8 1.460(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.336(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.453(3) . ?
C10 C11 1.403(3) . ?
C10 C15 1.398(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(3) . ?
C13 C14 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
N1L C1L 1.332(3) . ?
N1L C5L 1.329(3) . ?
N2L C8L 1.332(3) . ?
N2L C9L 1.332(3) . ?
C1L H1L 0.9300 . ?
C1L C2L 1.378(3) . ?
C2L H2L 0.9300 . ?
C2L C3L 1.379(3) . ?
C3L C4L 1.392(3) . ?
C3L C6L 1.484(3) . ?
C4L H4L 0.9300 . ?
C4L C5L 1.375(3) . ?
C5L H5L 0.9300 . ?
C6L C7L 1.389(3) . ?
C6L C10L 1.379(3) . ?
C7L H7L 0.9300 . ?
C7L C8L 1.369(3) . ?
C8L H8L 0.9300 . ?
C9L H9L 0.9300 . ?
C9L C10L 1.384(3) . ?
C10L H10L 0.9300 . ?

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 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
C13 O4 H4 109.5 . . ?
O1 C1 C2 117.9(2) . . ?
O1 C1 C6 121.4(2) . . ?
C2 C1 C6 120.7(2) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2A 119.8 . . ?
O2 C3 C2 123.3(2) . . ?
O2 C3 C4 116.8(2) . . ?
C2 C3 C4 119.9(2) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4A 120.2 . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.7(2) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C7 119.9(2) . . ?
C5 C6 C1 116.7(2) . . ?
C5 C6 C7 123.39(19) . . ?
O3 C7 C6 120.4(2) . . ?
O3 C7 C8 119.4(2) . . ?
C6 C7 C8 120.1(2) . . ?
C7 C8 H8 118.3 . . ?
C9 C8 C7 123.4(2) . . ?
C9 C8 H8 118.3 . . ?
C8 C9 H9 117.2 . . ?
C8 C9 C10 125.7(2) . . ?
C10 C9 H9 117.2 . . ?
C11 C10 C9 122.26(19) . . ?
C15 C10 C9 121.12(19) . . ?
C15 C10 C11 116.59(19) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
O4 C13 C12 116.5(2) . . ?
O4 C13 C14 124.47(19) . . ?
C12 C13 C14 119.0(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.83(19) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C5L N1L C1L 116.9(2) . . ?
C9L N2L C8L 116.53(19) . . ?
N1L C1L H1L 118.4 . . ?
N1L C1L C2L 123.1(2) . . ?
C2L C1L H1L 118.4 . . ?
C1L C2L H2L 120.0 . . ?
C1L C2L C3L 120.0(2) . . ?
C3L C2L H2L 120.0 . . ?
C2L C3L C4L 116.9(2) . . ?
C2L C3L C6L 121.99(19) . . ?
C4L C3L C6L 121.11(18) . . ?
C3L C4L H4L 120.4 . . ?
C5L C4L C3L 119.2(2) . . ?
C5L C4L H4L 120.4 . . ?
N1L C5L C4L 123.9(2) . . ?
N1L C5L H5L 118.1 . . ?
C4L C5L H5L 118.1 . . ?
C7L C6L C3L 121.04(18) . . ?
C10L C6L C3L 121.57(18) . . ?
C10L C6L C7L 117.4(2) . . ?
C6L C7L H7L 120.3 . . ?
C8L C7L C6L 119.4(2) . . ?
C8L C7L H7L 120.3 . . ?
N2L C8L C7L 123.9(2) . . ?
N2L C8L H8L 118.0 . . ?
C7L C8L H8L 118.0 . . ?
N2L C9L H9L 118.2 . . ?
N2L C9L C10L 123.6(2) . . ?
C10L C9L H9L 118.2 . . ?
C6L C10L C9L 119.20(19) . . ?
C6L C10L H10L 120.4 . . ?
C9L C10L H10L 120.4 . . ?

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 -179.1(2) . . . . ?
O1 C1 C6 C5 -180.0(2) . . . . ?
O1 C1 C6 C7 1.5(3) . . . . ?
O2 C3 C4 C5 -179.2(2) . . . . ?
O3 C7 C8 C9 -0.4(3) . . . . ?
O4 C13 C14 C15 -179.7(2) . . . . ?
C1 C2 C3 O2 179.4(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C6 C7 O3 -6.9(3) . . . . ?
C1 C6 C7 C8 170.20(19) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C1 C6 C7 -177.14(19) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 177.3(2) . . . . ?
C5 C6 C7 O3 174.68(19) . . . . ?
C5 C6 C7 C8 -8.3(3) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C7 C8 C9 -177.53(19) . . . . ?
C7 C8 C9 C10 178.78(19) . . . . ?
C8 C9 C10 C11 -6.9(3) . . . . ?
C8 C9 C10 C15 170.9(2) . . . . ?
C9 C10 C11 C12 177.6(2) . . . . ?
C9 C10 C15 C14 -177.75(19) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C11 C12 C13 O4 179.6(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C15 C10 C11 C12 -0.3(3) . . . . ?
N1L C1L C2L C3L 1.4(4) . . . . ?
N2L C9L C10L C6L 1.1(3) . . . . ?
C1L N1L C5L C4L -1.0(4) . . . . ?
C1L C2L C3L C4L -0.2(3) . . . . ?
C1L C2L C3L C6L -178.8(2) . . . . ?
C2L C3L C4L C5L -1.4(3) . . . . ?
C2L C3L C6L C7L 41.7(3) . . . . ?
C2L C3L C6L C10L -140.0(2) . . . . ?
C3L C4L C5L N1L 2.1(4) . . . . ?
C3L C6L C7L C8L 177.2(2) . . . . ?
C3L C6L C10L C9L -178.01(18) . . . . ?
C4L C3L C6L C7L -136.8(2) . . . . ?
C4L C3L C6L C10L 41.4(3) . . . . ?
C5L N1L C1L C2L -0.8(4) . . . . ?
C6L C3L C4L C5L 177.2(2) . . . . ?
C6L C7L C8L N2L 0.8(4) . . . . ?
C7L C6L C10L C9L 0.3(3) . . . . ?
C8L N2L C9L C10L -1.6(3) . . . . ?
C9L N2L C8L C7L 0.6(3) . . . . ?
C10L C6L C7L C8L -1.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
