# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_111
_audit_block_doi                 10.5517/ccdc.csd.cc2dzvkt
_database_code_depnum_ccdc_archive 'CCDC 2234187'
loop_
_audit_author_name
_audit_author_address
Pirfenidone-Hesperetin
;University of Science and Technology of China
China
;
_audit_update_record             
;
2023-04-21 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_audit_creation_date             2023-04-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O6, C12 H11 N O'
_chemical_formula_sum            'C28 H25 N O7'
_chemical_formula_weight         487.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.0415(10)
_cell_length_b                   6.6425(4)
_cell_length_c                   44.992(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4794.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      56.809
_cell_measurement_theta_min      2.943
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1389 before and 0.0819 after correction.
The Ratio of minimum to maximum transmission is 0.6982.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            27396
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         1.559
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           2.85
_diffrn_source_power             0.199101
_diffrn_source_voltage           69.86
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3666
_reflns_number_total             4864
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4864
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²+4.2983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.1960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C13B \\sim C13A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Others
 Sof(H14C)=Sof(H14D)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C13A)=Sof(H13A)=FVAR(1)
4.a Riding coordinates:
 O5(H5), O4(H4), O7(H7)
4.b Ternary CH refined with riding coordinates:
 C13A(H13A), C13B(H13B)
4.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D)
4.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C5(H5A), C24(H24), C3(H3), C27(H27), C23(H23), C8(H8),
 C2(H2), C9(H9), C12(H12), C10(H10), C11(H11)
4.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.69743(10) 0.1929(3) 0.45190(3) 0.0284(4) Uani 1 1 d . . . . .
O5 O 0.84468(11) 0.3322(3) 0.54014(4) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.895972 0.312247 0.526025 0.051 Uiso 1 1 d R U . . .
O3 O 0.47354(10) 0.2449(3) 0.49547(4) 0.0363(4) Uani 1 1 d . . . . .
O4 O 0.55269(11) 0.3435(3) 0.54341(4) 0.0361(5) Uani 1 1 d . . . . .
H4 H 0.506235 0.297642 0.529898 0.054 Uiso 1 1 d R U . . .
O6 O 0.63697(12) -0.0862(3) 0.31882(4) 0.0398(5) Uani 1 1 d . . . . .
O7 O 0.56069(13) 0.2517(3) 0.32901(4) 0.0437(5) Uani 1 1 d . . . . .
H7 H 0.534518 0.371512 0.334244 0.065 Uiso 1 1 d R U . . .
O1 O 0.47009(16) -0.4294(3) 0.34145(5) 0.0600(7) Uani 1 1 d . . . . .
N1 N 0.40279(14) -0.1338(3) 0.33258(5) 0.0336(5) Uani 1 1 d . . . . .
C20 C 0.69593(14) 0.2450(3) 0.48122(5) 0.0245(5) Uani 1 1 d . . . . .
C17 C 0.69905(15) 0.3407(4) 0.54179(5) 0.0280(5) Uani 1 1 d . . . . .
H17 H 0.701277 0.374217 0.562308 0.034 Uiso 1 1 calc R U . . .
C19 C 0.77112(14) 0.2641(3) 0.49531(5) 0.0255(5) Uani 1 1 d . . . . .
H19 H 0.821733 0.245196 0.484711 0.031 Uiso 1 1 calc R U . . .
C16 C 0.62395(15) 0.3199(4) 0.52760(5) 0.0277(5) Uani 1 1 d . . . . .
C21 C 0.61971(14) 0.2711(4) 0.49676(5) 0.0254(5) Uani 1 1 d . . . . .
C26 C 0.59673(16) 0.1618(4) 0.35281(5) 0.0308(6) Uani 1 1 d . . . . .
C18 C 0.77217(15) 0.3119(3) 0.52556(5) 0.0273(5) Uani 1 1 d . . . . .
C25 C 0.63766(15) -0.0227(4) 0.34768(5) 0.0312(6) Uani 1 1 d . . . . .
C15 C 0.54264(15) 0.2349(4) 0.48229(5) 0.0287(5) Uani 1 1 d . . . . .
C5 C 0.36981(17) 0.0447(4) 0.34243(6) 0.0362(6) Uani 1 1 d . . . . .
H5A H 0.347904 0.136330 0.328218 0.043 Uiso 1 1 calc R U . . .
C4 C 0.36718(17) 0.0956(4) 0.37138(6) 0.0364(6) Uani 1 1 d . . . . .
C22 C 0.63331(16) 0.1497(5) 0.40453(6) 0.0388(7) Uani 1 1 d . . . . .
C14 C 0.54645(16) 0.1745(5) 0.45021(6) 0.0358(6) Uani 1 1 d . . . . .
H14A H 0.497712 0.231806 0.439685 0.043 Uiso 0.850(7) 1 calc R U P A 1
H14B H 0.542784 0.026070 0.448808 0.043 Uiso 0.850(7) 1 calc R U P A 1
H14C H 0.500622 0.077927 0.446504 0.043 Uiso 0.150(7) 1 calc R U P A 2
H14D H 0.534842 0.295710 0.438083 0.043 Uiso 0.150(7) 1 calc R U P A 2
C24 C 0.67529(17) -0.1195(5) 0.37128(6) 0.0402(7) Uani 1 1 d . . . . .
H24 H 0.702895 -0.244381 0.368247 0.048 Uiso 1 1 calc R U . . .
C3 C 0.40182(18) -0.0447(4) 0.39178(6) 0.0391(6) Uani 1 1 d . . . . .
H3 H 0.399809 -0.016465 0.412470 0.047 Uiso 1 1 calc R U . . .
C27 C 0.59586(16) 0.2444(4) 0.38102(6) 0.0363(6) Uani 1 1 d . . . . .
H27 H 0.568667 0.369645 0.384170 0.044 Uiso 1 1 calc R U . . .
C23 C 0.67274(18) -0.0335(5) 0.39977(6) 0.0440(7) Uani 1 1 d . . . . .
H23 H 0.698294 -0.101376 0.415962 0.053 Uiso 1 1 calc R U . . .
C1 C 0.44007(18) -0.2724(4) 0.35160(6) 0.0394(6) Uani 1 1 d . . . . .
C7 C 0.39631(18) -0.1819(4) 0.30124(6) 0.0385(6) Uani 1 1 d . . . . .
C8 C 0.4414(2) -0.0741(5) 0.28088(6) 0.0500(8) Uani 1 1 d . . . . .
H8 H 0.478961 0.027885 0.287229 0.060 Uiso 1 1 calc R U . . .
C2 C 0.43752(18) -0.2172(5) 0.38235(6) 0.0415(7) Uani 1 1 d . . . . .
H2 H 0.461801 -0.304948 0.396597 0.050 Uiso 1 1 calc R U . . .
C13A C 0.62508(17) 0.2440(5) 0.43496(6) 0.0276(8) Uani 0.850(7) 1 d . U P A 1
H13A H 0.622811 0.393627 0.432652 0.033 Uiso 0.850(7) 1 calc R U P A 1
C9 C 0.4316(2) -0.1158(6) 0.25082(7) 0.0596(9) Uani 1 1 d . . . . .
H9 H 0.462343 -0.041512 0.236496 0.072 Uiso 1 1 calc R U . . .
C28 C 0.6775(2) -0.2714(5) 0.31232(7) 0.0534(8) Uani 1 1 d . . . . .
H28A H 0.671334 -0.301966 0.291125 0.080 Uiso 1 1 calc R U . . .
H28B H 0.652205 -0.379456 0.324106 0.080 Uiso 1 1 calc R U . . .
H28C H 0.736805 -0.260507 0.317255 0.080 Uiso 1 1 calc R U . . .
C12 C 0.3417(2) -0.3299(5) 0.29244(7) 0.0546(8) Uani 1 1 d . . . . .
H12 H 0.310752 -0.403581 0.306795 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3282(2) 0.2897(5) 0.38180(8) 0.0578(9) Uani 1 1 d . . . . .
H6A H 0.313481 0.372460 0.364546 0.087 Uiso 1 1 calc R U . . .
H6B H 0.368021 0.362995 0.394296 0.087 Uiso 1 1 calc R U . . .
H6C H 0.277884 0.259959 0.393324 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3778(2) -0.2636(7) 0.24176(7) 0.0624(10) Uani 1 1 d . . . . .
H10 H 0.371855 -0.292508 0.221190 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3322(2) -0.3706(7) 0.26238(8) 0.0655(10) Uani 1 1 d . . . . .
H11 H 0.294416 -0.471908 0.256020 0.079 Uiso 1 1 calc R U . . .
C13B C 0.6178(9) 0.091(3) 0.4400(4) 0.028(4) Uani 0.150(7) 1 d . U P A 2
H13B H 0.618827 -0.057875 0.443241 0.033 Uiso 0.150(7) 1 calc R U P A 2


_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
O2 C20 1.364(3) . ?
O2 C13A 1.429(3) . ?
O2 C13B 1.542(15) . ?
O5 H5 1.0479 . ?
O5 C18 1.342(3) . ?
O3 C15 1.259(3) . ?
O4 H4 1.0088 . ?
O4 C16 1.356(3) . ?
O6 C25 1.366(3) . ?
O6 C28 1.421(3) . ?
O7 H7 0.9301 . ?
O7 C26 1.355(3) . ?
O1 C1 1.236(3) . ?
N1 C5 1.372(3) . ?
N1 C1 1.392(3) . ?
N1 C7 1.449(3) . ?
C20 C19 1.368(3) . ?
C20 C21 1.419(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.371(3) . ?
C17 C18 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.398(3) . ?
C16 C21 1.427(3) . ?
C21 C15 1.418(3) . ?
C26 C25 1.409(4) . ?
C26 C27 1.383(3) . ?
C25 C24 1.381(4) . ?
C15 C14 1.499(3) . ?
C5 H5A 0.9500 . ?
C5 C4 1.346(4) . ?
C4 C3 1.421(4) . ?
C4 C6 1.508(4) . ?
C22 C27 1.369(4) . ?
C22 C23 1.388(4) . ?
C22 C13A 1.512(4) . ?
C22 C13B 1.661(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 C13A 1.508(4) . ?
C14 C13B 1.352(16) . ?
C24 H24 0.9500 . ?
C24 C23 1.404(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.349(4) . ?
C27 H27 0.9500 . ?
C23 H23 0.9500 . ?
C1 C2 1.432(4) . ?
C7 C8 1.370(4) . ?
C7 C12 1.375(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(4) . ?
C2 H2 0.9500 . ?
C13A H13A 1.0000 . ?
C9 H9 0.9500 . ?
C9 C10 1.369(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C11 1.388(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9500 . ?
C13B H13B 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O2 C13A 116.19(18) . . ?
C20 O2 C13B 115.7(6) . . ?
C18 O5 H5 111.8 . . ?
C16 O4 H4 105.8 . . ?
C25 O6 C28 117.4(2) . . ?
C26 O7 H7 111.7 . . ?
C5 N1 C1 122.6(2) . . ?
C5 N1 C7 118.5(2) . . ?
C1 N1 C7 118.9(2) . . ?
O2 C20 C19 117.1(2) . . ?
O2 C20 C21 121.5(2) . . ?
C19 C20 C21 121.3(2) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(2) . . ?
C18 C17 H17 120.6 . . ?
C20 C19 H19 120.6 . . ?
C20 C19 C18 118.9(2) . . ?
C18 C19 H19 120.6 . . ?
O4 C16 C17 119.0(2) . . ?
O4 C16 C21 119.8(2) . . ?
C17 C16 C21 121.2(2) . . ?
C20 C21 C16 117.8(2) . . ?
C15 C21 C20 120.3(2) . . ?
C15 C21 C16 121.8(2) . . ?
O7 C26 C25 116.9(2) . . ?
O7 C26 C27 123.1(2) . . ?
C27 C26 C25 120.0(2) . . ?
O5 C18 C17 117.3(2) . . ?
O5 C18 C19 120.6(2) . . ?
C17 C18 C19 122.1(2) . . ?
O6 C25 C26 114.9(2) . . ?
O6 C25 C24 126.2(2) . . ?
C24 C25 C26 118.9(2) . . ?
O3 C15 C21 122.9(2) . . ?
O3 C15 C14 120.2(2) . . ?
C21 C15 C14 116.9(2) . . ?
N1 C5 H5A 118.6 . . ?
C4 C5 N1 122.8(3) . . ?
C4 C5 H5A 118.6 . . ?
C5 C4 C3 116.6(3) . . ?
C5 C4 C6 121.9(3) . . ?
C3 C4 C6 121.5(3) . . ?
C27 C22 C23 118.9(3) . . ?
C27 C22 C13A 118.1(3) . . ?
C27 C22 C13B 141.6(6) . . ?
C23 C22 C13A 122.9(3) . . ?
C23 C22 C13B 90.6(6) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C15 C14 H14C 107.8 . . ?
C15 C14 H14D 107.8 . . ?
C15 C14 C13A 113.0(2) . . ?
H14A C14 H14B 107.8 . . ?
H14C C14 H14D 107.1 . . ?
C13A C14 H14A 109.0 . . ?
C13A C14 H14B 109.0 . . ?
C13B C14 C15 118.1(7) . . ?
C13B C14 H14C 107.8 . . ?
C13B C14 H14D 107.8 . . ?
C25 C24 H24 120.0 . . ?
C25 C24 C23 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C26 C27 H27 119.3 . . ?
C22 C27 C26 121.5(3) . . ?
C22 C27 H27 119.3 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
O1 C1 N1 119.9(3) . . ?
O1 C1 C2 125.8(3) . . ?
N1 C1 C2 114.4(2) . . ?
C8 C7 N1 119.8(3) . . ?
C8 C7 C12 121.2(3) . . ?
C12 C7 N1 118.9(3) . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
O2 C13A C22 108.3(2) . . ?
O2 C13A C14 111.3(2) . . ?
O2 C13A H13A 108.7 . . ?
C22 C13A H13A 108.7 . . ?
C14 C13A C22 111.0(2) . . ?
C14 C13A H13A 108.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C7 C12 H12 120.3 . . ?
C7 C12 C11 119.3(3) . . ?
C11 C12 H12 120.3 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
O2 C13B C22 96.1(8) . . ?
O2 C13B H13B 111.7 . . ?
C22 C13B H13B 111.7 . . ?
C14 C13B O2 113.8(12) . . ?
C14 C13B C22 110.9(11) . . ?
C14 C13B H13B 111.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C20 C19 C18 -178.3(2) . . . . ?
O2 C20 C21 C16 178.2(2) . . . . ?
O2 C20 C21 C15 2.7(4) . . . . ?
O3 C15 C14 C13A 158.1(2) . . . . ?
O3 C15 C14 C13B -154.8(9) . . . . ?
O4 C16 C21 C20 -179.1(2) . . . . ?
O4 C16 C21 C15 -3.7(4) . . . . ?
O6 C25 C24 C23 178.4(3) . . . . ?
O7 C26 C25 O6 1.1(3) . . . . ?
O7 C26 C25 C24 180.0(2) . . . . ?
O7 C26 C27 C22 -179.7(3) . . . . ?
O1 C1 C2 C3 -178.4(3) . . . . ?
N1 C5 C4 C3 0.9(4) . . . . ?
N1 C5 C4 C6 -178.1(3) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
N1 C7 C8 C9 -177.0(3) . . . . ?
N1 C7 C12 C11 177.0(3) . . . . ?
C20 O2 C13A C22 -172.3(2) . . . . ?
C20 O2 C13A C14 -50.0(3) . . . . ?
C20 O2 C13B C22 157.1(4) . . . . ?
C20 O2 C13B C14 41.1(13) . . . . ?
C20 C19 C18 O5 -179.9(2) . . . . ?
C20 C19 C18 C17 0.0(4) . . . . ?
C20 C21 C15 O3 175.9(2) . . . . ?
C20 C21 C15 C14 -1.6(4) . . . . ?
C17 C16 C21 C20 -0.1(4) . . . . ?
C17 C16 C21 C15 175.4(2) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C19 C20 C21 C15 -175.0(2) . . . . ?
C16 C17 C18 O5 -179.6(2) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C16 C21 C15 O3 0.6(4) . . . . ?
C16 C21 C15 C14 -176.9(2) . . . . ?
C21 C20 C19 C18 -0.5(4) . . . . ?
C21 C15 C14 C13A -24.3(3) . . . . ?
C21 C15 C14 C13B 22.8(9) . . . . ?
C26 C25 C24 C23 -0.3(4) . . . . ?
C18 C17 C16 O4 178.6(2) . . . . ?
C18 C17 C16 C21 -0.5(4) . . . . ?
C25 C26 C27 C22 -0.8(4) . . . . ?
C25 C24 C23 C22 -0.6(4) . . . . ?
C15 C14 C13A O2 49.3(3) . . . . ?
C15 C14 C13A C22 170.1(2) . . . . ?
C15 C14 C13B O2 -41.1(14) . . . . ?
C15 C14 C13B C22 -148.1(6) . . . . ?
C5 N1 C1 O1 -178.7(3) . . . . ?
C5 N1 C1 C2 2.8(4) . . . . ?
C5 N1 C7 C8 69.3(4) . . . . ?
C5 N1 C7 C12 -107.8(3) . . . . ?
C5 C4 C3 C2 1.8(4) . . . . ?
C4 C3 C2 C1 -2.2(4) . . . . ?
C27 C26 C25 O6 -177.8(2) . . . . ?
C27 C26 C25 C24 1.0(4) . . . . ?
C27 C22 C23 C24 0.8(4) . . . . ?
C27 C22 C13A O2 -150.5(2) . . . . ?
C27 C22 C13A C14 86.9(3) . . . . ?
C27 C22 C13B O2 -124.1(7) . . . . ?
C27 C22 C13B C14 -5.8(18) . . . . ?
C23 C22 C27 C26 -0.2(4) . . . . ?
C23 C22 C13A O2 33.3(4) . . . . ?
C23 C22 C13A C14 -89.2(3) . . . . ?
C23 C22 C13B O2 93.5(8) . . . . ?
C23 C22 C13B C14 -148.2(10) . . . . ?
C1 N1 C5 C4 -3.4(4) . . . . ?
C1 N1 C7 C8 -112.4(3) . . . . ?
C1 N1 C7 C12 70.5(4) . . . . ?
C7 N1 C5 C4 174.8(3) . . . . ?
C7 N1 C1 O1 3.1(4) . . . . ?
C7 N1 C1 C2 -175.4(2) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C7 C12 C11 C10 0.4(6) . . . . ?
C8 C7 C12 C11 0.0(5) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C13A O2 C20 C19 -157.8(2) . . . . ?
C13A O2 C20 C21 24.4(3) . . . . ?
C13A C22 C27 C26 -176.4(3) . . . . ?
C13A C22 C23 C24 176.9(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C28 O6 C25 C26 179.9(2) . . . . ?
C28 O6 C25 C24 1.2(4) . . . . ?
C12 C7 C8 C9 0.0(5) . . . . ?
C6 C4 C3 C2 -179.2(3) . . . . ?
C13B O2 C20 C19 156.3(8) . . . . ?
C13B O2 C20 C21 -21.5(8) . . . . ?
C13B C22 C27 C26 -136.0(10) . . . . ?
C13B C22 C23 C24 155.2(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_t
_audit_block_doi                 10.5517/ccdc.csd.cc2dfmn4
_database_code_depnum_ccdc_archive 'CCDC 2217636'
loop_
_audit_author_name
_audit_author_address
Pirfenidone-Genistein
;University of Science and Technology of China
China
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_audit_creation_date             2023-02-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O5, 2(C12 H11 N O)'
_chemical_formula_sum            'C39 H32 N2 O7'
_chemical_formula_weight         640.66
_chemical_absolute_configuration ?
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   18.9053(6)
_cell_length_b                   8.2831(2)
_cell_length_c                   20.9395(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.594(2)
_cell_angle_gamma                90
_cell_volume                     3242.19(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.098
_cell_measurement_theta_min      4.271
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3766
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0909 after correction.
The Ratio of minimum to maximum transmission is 0.4997.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21466
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.806
_diffrn_reflns_theta_min         4.271
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                5684
_reflns_number_total             6267
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.126
_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)+(0.1275P)²+0.0028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1822
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(3)
 0.2(3)
2. 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
3.a Riding coordinates:
 O5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C23(H23), C24(H24), C26(H26), C17(H17), C27(H27), C19(H19),
 C5A(H5A), C3A(H3A), C2A(H2A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C12A(H12A), C5B(H5B), C3B(H3B), C2B(H2B), C12B(H12B), C11B(H11B), C10B(H10B),
 C9B(H9B), C8B(H8B)
3.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.25670(16) 1.4190(3) 0.33899(14) 0.0603(7) Uani 1 1 d . . . . .
O3 O 0.20912(17) 0.9665(3) 0.39716(14) 0.0635(7) Uani 1 1 d . . . . .
O4 O 0.15377(19) 1.0948(4) 0.49174(16) 0.0688(8) Uani 1 1 d . . . . .
H4 H 0.171(4) 1.026(10) 0.458(3) 0.103 Uiso 1 1 d . U . . .
O5 O 0.14578(19) 1.6690(4) 0.49716(18) 0.0742(8) Uani 1 1 d . . . . .
H5 H 0.133899 1.650772 0.532564 0.111 Uiso 1 1 d R U . . .
O6 O 0.25959(19) 0.6350(4) 0.13622(15) 0.0700(8) Uani 1 1 d . . . . .
H6 H 0.284(4) 0.538(11) 0.154(3) 0.105 Uiso 1 1 d . U . . .
C22 C 0.25781(19) 1.0025(4) 0.27180(17) 0.0517(7) Uani 1 1 d . . . . .
C13 C 0.2679(2) 1.2856(5) 0.3045(2) 0.0578(8) Uani 1 1 d . . . . .
H13 H 0.289296 1.300717 0.267694 0.069 Uiso 1 1 calc R U . . .
C23 C 0.2312(2) 1.0256(5) 0.20615(19) 0.0587(9) Uani 1 1 d . . . . .
H23 H 0.211706 1.125053 0.192374 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2509(2) 1.1331(5) 0.31842(18) 0.0518(8) Uani 1 1 d . . . . .
C24 C 0.2334(2) 0.9030(5) 0.16164(19) 0.0629(9) Uani 1 1 d . . . . .
H24 H 0.216236 0.921265 0.118270 0.076 Uiso 1 1 calc R U . . .
C15 C 0.22162(19) 1.1035(4) 0.37799(17) 0.0498(8) Uani 1 1 d . . . . .
C25 C 0.2610(2) 0.7534(5) 0.18126(19) 0.0546(8) Uani 1 1 d . . . . .
C16 C 0.1699(2) 1.2391(5) 0.46743(18) 0.0530(8) Uani 1 1 d . . . . .
C26 C 0.2896(2) 0.7291(5) 0.24607(19) 0.0561(8) Uani 1 1 d . . . . .
H26 H 0.310296 0.630639 0.259427 0.067 Uiso 1 1 calc R U . . .
C17 C 0.1503(2) 1.3786(6) 0.4963(2) 0.0605(9) Uani 1 1 d . . . . .
H17 H 0.126744 1.372294 0.532204 0.073 Uiso 1 1 calc R U . . .
C27 C 0.2868(2) 0.8530(5) 0.29049(18) 0.0548(8) Uani 1 1 d . . . . .
H27 H 0.304828 0.835170 0.333711 0.066 Uiso 1 1 calc R U . . .
C18 C 0.16576(19) 1.5299(5) 0.47156(19) 0.0572(8) Uani 1 1 d . . . . .
C19 C 0.2026(2) 1.5425(5) 0.41928(19) 0.0567(8) Uani 1 1 d . . . . .
H19 H 0.214334 1.642548 0.403686 0.068 Uiso 1 1 calc R U . . .
C20 C 0.22104(18) 1.4015(4) 0.39136(18) 0.0509(8) Uani 1 1 d . . . . .
C21 C 0.20550(19) 1.2468(5) 0.41279(18) 0.0490(7) Uani 1 1 d . . . . .
O1A O 0.34030(17) 0.3807(4) 0.17950(15) 0.0654(7) Uani 1 1 d . . . . .
N1A N 0.42249(17) 0.2160(4) 0.14301(15) 0.0535(7) Uani 1 1 d . . . . .
C5A C 0.4467(3) 0.1335(5) 0.0934(2) 0.0624(9) Uani 1 1 d . . . . .
H5A H 0.492595 0.089967 0.100085 0.075 Uiso 1 1 calc R U . . .
C4A C 0.4058(3) 0.1139(5) 0.0351(2) 0.0724(12) Uani 1 1 d . . . . .
C3A C 0.3356(3) 0.1763(7) 0.0282(2) 0.0794(13) Uani 1 1 d . . . . .
H3A H 0.304839 0.158073 -0.010130 0.095 Uiso 1 1 calc R U . . .
C2A C 0.3118(3) 0.2624(7) 0.0760(2) 0.0725(11) Uani 1 1 d . . . . .
H2A H 0.265368 0.302658 0.069779 0.087 Uiso 1 1 calc R U . . .
C1A C 0.3571(2) 0.2916(5) 0.13545(19) 0.0554(8) Uani 1 1 d . . . . .
C6A C 0.4348(5) 0.0285(8) -0.0189(3) 0.101(2) Uani 1 1 d . . . . .
H6AA H 0.447681 0.106625 -0.048970 0.151 Uiso 1 1 calc R U . . .
H6AB H 0.398903 -0.042619 -0.040598 0.151 Uiso 1 1 calc R U . . .
H6AC H 0.476254 -0.033009 -0.001486 0.151 Uiso 1 1 calc R U . . .
C7A C 0.4685(2) 0.2275(5) 0.20453(19) 0.0542(8) Uani 1 1 d . . . . .
C8A C 0.5357(2) 0.2945(6) 0.2091(3) 0.0684(10) Uani 1 1 d . . . . .
H8A H 0.552702 0.330448 0.172171 0.082 Uiso 1 1 calc R U . . .
C9A C 0.5777(3) 0.3081(7) 0.2688(3) 0.0843(15) Uani 1 1 d . . . . .
H9A H 0.623372 0.351964 0.272014 0.101 Uiso 1 1 calc R U . . .
C10A C 0.5523(3) 0.2572(7) 0.3232(3) 0.0873(16) Uani 1 1 d . . . . .
H10A H 0.580270 0.270008 0.363391 0.105 Uiso 1 1 calc R U . . .
C11A C 0.4856(3) 0.1872(8) 0.3192(3) 0.0824(14) Uani 1 1 d . . . . .
H11A H 0.469155 0.150731 0.356324 0.099 Uiso 1 1 calc R U . . .
C12A C 0.4431(2) 0.1713(6) 0.2595(2) 0.0642(10) Uani 1 1 d . . . . .
H12A H 0.398186 0.123553 0.256197 0.077 Uiso 1 1 calc R U . . .
O1B O 0.0912(2) 0.3840(5) 0.10356(18) 0.0822(10) Uani 1 1 d . . . . .
N1B N 0.01651(17) 0.2287(4) 0.15477(15) 0.0528(7) Uani 1 1 d . . . . .
C5B C -0.0090(2) 0.1824(5) 0.2101(2) 0.0591(8) Uani 1 1 d . . . . .
H5B H -0.046283 0.108300 0.207177 0.071 Uiso 1 1 calc R U . . .
C4B C 0.0189(3) 0.2422(6) 0.2691(2) 0.0684(11) Uani 1 1 d . . . . .
C3B C 0.0755(3) 0.3522(7) 0.2708(3) 0.0768(13) Uani 1 1 d . . . . .
H3B H 0.095797 0.394559 0.310470 0.092 Uiso 1 1 calc R U . . .
C2B C 0.1015(2) 0.3989(6) 0.2172(2) 0.0696(11) Uani 1 1 d . . . . .
H2B H 0.139326 0.471797 0.220751 0.084 Uiso 1 1 calc R U . . .
C1B C 0.0722(2) 0.3383(5) 0.1553(2) 0.0597(9) Uani 1 1 d . . . . .
C6B C -0.0094(4) 0.1874(11) 0.3293(3) 0.104(2) Uani 1 1 d . . . . .
H6BA H -0.033338 0.275788 0.346722 0.155 Uiso 1 1 calc R U . . .
H6BB H 0.029606 0.151511 0.360768 0.155 Uiso 1 1 calc R U . . .
H6BC H -0.042571 0.100227 0.318753 0.155 Uiso 1 1 calc R U . . .
C7B C -0.0192(2) 0.1660(5) 0.09413(18) 0.0544(8) Uani 1 1 d . . . . .
C12B C 0.0194(3) 0.0812(6) 0.0536(2) 0.0670(10) Uani 1 1 d . . . . .
H12B H 0.068405 0.065400 0.064765 0.080 Uiso 1 1 calc R U . . .
C11B C -0.0166(3) 0.0209(8) -0.0039(2) 0.0844(14) Uani 1 1 d . . . . .
H11B H 0.008231 -0.036375 -0.031603 0.101 Uiso 1 1 calc R U . . .
C10B C -0.0886(3) 0.0450(9) -0.0200(3) 0.0882(16) Uani 1 1 d . . . . .
H10B H -0.112057 0.006083 -0.059189 0.106 Uiso 1 1 calc R U . . .
C9B C -0.1265(3) 0.1258(8) 0.0207(3) 0.0814(14) Uani 1 1 d . . . . .
H9B H -0.175690 0.138249 0.009918 0.098 Uiso 1 1 calc R U . . .
C8B C -0.0914(2) 0.1889(6) 0.0779(2) 0.0661(10) Uani 1 1 d . . . . .
H8B H -0.116699 0.246524 0.105209 0.079 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
O2 C13 1.355(5) . ?
O2 C20 1.378(5) . ?
O3 C15 1.238(5) . ?
O4 H4 1.00(8) . ?
O4 C16 1.352(5) . ?
O5 H5 0.8200 . ?
O5 C18 1.348(5) . ?
O6 H6 0.98(8) . ?
O6 C25 1.358(5) . ?
C22 C23 1.405(5) . ?
C22 C14 1.476(5) . ?
C22 C27 1.387(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.346(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(6) . ?
C14 C15 1.459(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(6) . ?
C15 C21 1.449(5) . ?
C25 C26 1.398(5) . ?
C16 C17 1.380(6) . ?
C16 C21 1.413(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.404(6) . ?
C27 H27 0.9300 . ?
C18 C19 1.386(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(5) . ?
C20 C21 1.403(5) . ?
O1A C1A 1.259(5) . ?
N1A C5A 1.379(5) . ?
N1A C1A 1.373(5) . ?
N1A C7A 1.446(5) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.353(7) . ?
C4A C3A 1.410(8) . ?
C4A C6A 1.505(7) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.360(8) . ?
C2A H2A 0.9300 . ?
C2A C1A 1.422(6) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C7A C8A 1.375(6) . ?
C7A C12A 1.391(6) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.383(8) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.367(9) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.379(9) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.388(7) . ?
C12A H12A 0.9300 . ?
O1B C1B 1.250(6) . ?
N1B C5B 1.374(5) . ?
N1B C1B 1.389(5) . ?
N1B C7B 1.442(5) . ?
C5B H5B 0.9300 . ?
C5B C4B 1.361(6) . ?
C4B C3B 1.401(8) . ?
C4B C6B 1.512(8) . ?
C3B H3B 0.9300 . ?
C3B C2B 1.349(8) . ?
C2B H2B 0.9300 . ?
C2B C1B 1.423(6) . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C7B C12B 1.390(6) . ?
C7B C8B 1.371(6) . ?
C12B H12B 0.9300 . ?
C12B C11B 1.384(7) . ?
C11B H11B 0.9300 . ?
C11B C10B 1.366(9) . ?
C10B H10B 0.9300 . ?
C10B C9B 1.368(9) . ?
C9B H9B 0.9300 . ?
C9B C8B 1.382(7) . ?
C8B H8B 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
C13 O2 C20 118.2(3) . . ?
C16 O4 H4 97(4) . . ?
C18 O5 H5 109.5 . . ?
C25 O6 H6 112(4) . . ?
C23 C22 C14 119.6(3) . . ?
C27 C22 C23 117.8(3) . . ?
C27 C22 C14 122.6(3) . . ?
O2 C13 H13 117.0 . . ?
C14 C13 O2 126.0(4) . . ?
C14 C13 H13 117.0 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C13 C14 C22 119.8(3) . . ?
C13 C14 C15 118.5(3) . . ?
C15 C14 C22 121.7(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
O3 C15 C14 123.1(3) . . ?
O3 C15 C21 121.5(3) . . ?
C21 C15 C14 115.3(3) . . ?
O6 C25 C24 118.3(4) . . ?
O6 C25 C26 122.3(3) . . ?
C24 C25 C26 119.4(3) . . ?
O4 C16 C17 119.0(4) . . ?
O4 C16 C21 120.4(3) . . ?
C17 C16 C21 120.6(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C22 C27 C26 121.5(3) . . ?
C22 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
O5 C18 C17 122.0(4) . . ?
O5 C18 C19 117.0(4) . . ?
C19 C18 C17 121.0(4) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 C18 117.5(4) . . ?
C20 C19 H19 121.2 . . ?
O2 C20 C21 120.1(3) . . ?
C19 C20 O2 115.8(3) . . ?
C19 C20 C21 124.1(3) . . ?
C16 C21 C15 122.1(3) . . ?
C20 C21 C15 121.2(3) . . ?
C20 C21 C16 116.6(3) . . ?
C5A N1A C7A 118.7(3) . . ?
C1A N1A C5A 122.3(3) . . ?
C1A N1A C7A 119.0(3) . . ?
N1A C5A H5A 119.0 . . ?
C4A C5A N1A 121.9(4) . . ?
C4A C5A H5A 119.0 . . ?
C5A C4A C3A 116.9(4) . . ?
C5A C4A C6A 120.6(5) . . ?
C3A C4A C6A 122.5(5) . . ?
C4A C3A H3A 119.1 . . ?
C2A C3A C4A 121.7(4) . . ?
C2A C3A H3A 119.1 . . ?
C3A C2A H2A 119.6 . . ?
C3A C2A C1A 120.8(5) . . ?
C1A C2A H2A 119.6 . . ?
O1A C1A N1A 120.3(3) . . ?
O1A C1A C2A 123.8(4) . . ?
N1A C1A C2A 115.9(4) . . ?
C4A C6A H6AA 109.5 . . ?
C4A C6A H6AB 109.5 . . ?
C4A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C8A C7A N1A 121.0(4) . . ?
C8A C7A C12A 120.4(4) . . ?
C12A C7A N1A 118.6(4) . . ?
C7A C8A H8A 120.1 . . ?
C7A C8A C9A 119.7(5) . . ?
C9A C8A H8A 120.1 . . ?
C8A C9A H9A 119.9 . . ?
C10A C9A C8A 120.2(5) . . ?
C10A C9A H9A 119.9 . . ?
C9A C10A H10A 119.7 . . ?
C9A C10A C11A 120.7(5) . . ?
C11A C10A H10A 119.7 . . ?
C10A C11A H11A 120.1 . . ?
C10A C11A C12A 119.8(5) . . ?
C12A C11A H11A 120.1 . . ?
C7A C12A H12A 120.4 . . ?
C11A C12A C7A 119.2(5) . . ?
C11A C12A H12A 120.4 . . ?
C5B N1B C1B 122.4(3) . . ?
C5B N1B C7B 117.7(3) . . ?
C1B N1B C7B 119.8(3) . . ?
N1B C5B H5B 119.1 . . ?
C4B C5B N1B 121.8(4) . . ?
C4B C5B H5B 119.1 . . ?
C5B C4B C3B 116.8(4) . . ?
C5B C4B C6B 120.7(5) . . ?
C3B C4B C6B 122.5(5) . . ?
C4B C3B H3B 118.8 . . ?
C2B C3B C4B 122.5(4) . . ?
C2B C3B H3B 118.8 . . ?
C3B C2B H2B 119.5 . . ?
C3B C2B C1B 121.1(4) . . ?
C1B C2B H2B 119.5 . . ?
O1B C1B N1B 120.5(4) . . ?
O1B C1B C2B 124.0(4) . . ?
N1B C1B C2B 115.4(4) . . ?
C4B C6B H6BA 109.5 . . ?
C4B C6B H6BB 109.5 . . ?
C4B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C12B C7B N1B 120.1(3) . . ?
C8B C7B N1B 119.1(4) . . ?
C8B C7B C12B 120.9(4) . . ?
C7B C12B H12B 120.7 . . ?
C11B C12B C7B 118.6(4) . . ?
C11B C12B H12B 120.7 . . ?
C12B C11B H11B 119.8 . . ?
C10B C11B C12B 120.3(5) . . ?
C10B C11B H11B 119.8 . . ?
C11B C10B H10B 119.6 . . ?
C11B C10B C9B 120.8(5) . . ?
C9B C10B H10B 119.6 . . ?
C10B C9B H9B 120.1 . . ?
C10B C9B C8B 119.8(5) . . ?
C8B C9B H9B 120.1 . . ?
C7B C8B C9B 119.6(5) . . ?
C7B C8B H8B 120.2 . . ?
C9B C8B H8B 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O3 1.00(8) 1.63(8) 2.601(4) 162(7) . yes
O5 H5 O1B 0.82 1.82 2.628(5) 169.6 2_575 yes
O6 H6 O1A 0.98(8) 1.71(8) 2.678(4) 170(7) . yes
C13 H13 O1A 0.93 2.30 3.227(5) 171.0 1_565 yes
C17 H17 O1B 0.93 2.66 3.302(5) 127.1 2_575 yes
C5A H5A O1B 0.93 2.52 3.406(6) 159.3 3_545 yes
C2A H2A O5 0.93 2.54 3.369(6) 148.7 2_574 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C13 C14 C22 172.1(4) . . . . ?
O2 C13 C14 C15 -4.0(6) . . . . ?
O2 C20 C21 C15 -4.6(5) . . . . ?
O2 C20 C21 C16 179.0(3) . . . . ?
O3 C15 C21 C16 -4.9(5) . . . . ?
O3 C15 C21 C20 178.8(3) . . . . ?
O4 C16 C17 C18 -179.4(3) . . . . ?
O4 C16 C21 C15 4.4(5) . . . . ?
O4 C16 C21 C20 -179.1(3) . . . . ?
O5 C18 C19 C20 -177.8(3) . . . . ?
O6 C25 C26 C27 -177.3(4) . . . . ?
C22 C23 C24 C25 1.1(7) . . . . ?
C22 C14 C15 O3 9.2(5) . . . . ?
C22 C14 C15 C21 -168.8(3) . . . . ?
C13 O2 C20 C19 -171.5(3) . . . . ?
C13 O2 C20 C21 8.2(5) . . . . ?
C13 C14 C15 O3 -174.8(4) . . . . ?
C13 C14 C15 C21 7.3(5) . . . . ?
C23 C22 C14 C13 -46.2(5) . . . . ?
C23 C22 C14 C15 129.8(4) . . . . ?
C23 C22 C27 C26 -0.1(6) . . . . ?
C23 C24 C25 O6 177.5(4) . . . . ?
C23 C24 C25 C26 -2.8(7) . . . . ?
C14 C22 C23 C24 -176.6(4) . . . . ?
C14 C22 C27 C26 176.8(4) . . . . ?
C14 C15 C21 C16 173.1(3) . . . . ?
C14 C15 C21 C20 -3.2(5) . . . . ?
C24 C25 C26 C27 3.0(6) . . . . ?
C25 C26 C27 C22 -1.6(6) . . . . ?
C16 C17 C18 O5 178.1(4) . . . . ?
C16 C17 C18 C19 -1.9(6) . . . . ?
C17 C16 C21 C15 -174.8(3) . . . . ?
C17 C16 C21 C20 1.7(5) . . . . ?
C17 C18 C19 C20 2.2(5) . . . . ?
C27 C22 C23 C24 0.4(6) . . . . ?
C27 C22 C14 C13 137.0(4) . . . . ?
C27 C22 C14 C15 -47.0(5) . . . . ?
C18 C19 C20 O2 179.1(3) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C19 C20 C21 C15 175.1(3) . . . . ?
C19 C20 C21 C16 -1.4(5) . . . . ?
C20 O2 C13 C14 -4.0(6) . . . . ?
C21 C16 C17 C18 -0.2(6) . . . . ?
N1A C5A C4A C3A -2.5(7) . . . . ?
N1A C5A C4A C6A 177.7(5) . . . . ?
N1A C7A C8A C9A 178.1(4) . . . . ?
N1A C7A C12A C11A -177.5(4) . . . . ?
C5A N1A C1A O1A -171.9(4) . . . . ?
C5A N1A C1A C2A 7.8(6) . . . . ?
C5A N1A C7A C8A 57.6(5) . . . . ?
C5A N1A C7A C12A -123.2(4) . . . . ?
C5A C4A C3A C2A 4.7(8) . . . . ?
C4A C3A C2A C1A -0.5(8) . . . . ?
C3A C2A C1A O1A 174.2(5) . . . . ?
C3A C2A C1A N1A -5.6(7) . . . . ?
C1A N1A C5A C4A -3.9(6) . . . . ?
C1A N1A C7A C8A -120.5(4) . . . . ?
C1A N1A C7A C12A 58.7(5) . . . . ?
C6A C4A C3A C2A -175.6(5) . . . . ?
C7A N1A C5A C4A 178.0(4) . . . . ?
C7A N1A C1A O1A 6.1(5) . . . . ?
C7A N1A C1A C2A -174.1(4) . . . . ?
C7A C8A C9A C10A -0.9(8) . . . . ?
C8A C7A C12A C11A 1.6(7) . . . . ?
C8A C9A C10A C11A 2.1(9) . . . . ?
C9A C10A C11A C12A -1.4(9) . . . . ?
C10A C11A C12A C7A -0.4(8) . . . . ?
C12A C7A C8A C9A -1.0(7) . . . . ?
N1B C5B C4B C3B -0.6(6) . . . . ?
N1B C5B C4B C6B -179.1(5) . . . . ?
N1B C7B C12B C11B 179.2(5) . . . . ?
N1B C7B C8B C9B -178.3(4) . . . . ?
C5B N1B C1B O1B -176.1(4) . . . . ?
C5B N1B C1B C2B 0.5(6) . . . . ?
C5B N1B C7B C12B -123.6(4) . . . . ?
C5B N1B C7B C8B 55.3(5) . . . . ?
C5B C4B C3B C2B 0.4(7) . . . . ?
C4B C3B C2B C1B 0.3(7) . . . . ?
C3B C2B C1B O1B 175.7(4) . . . . ?
C3B C2B C1B N1B -0.7(6) . . . . ?
C1B N1B C5B C4B 0.2(6) . . . . ?
C1B N1B C7B C12B 59.7(5) . . . . ?
C1B N1B C7B C8B -121.5(4) . . . . ?
C6B C4B C3B C2B 178.8(5) . . . . ?
C7B N1B C5B C4B -176.5(4) . . . . ?
C7B N1B C1B O1B 0.6(6) . . . . ?
C7B N1B C1B C2B 177.1(3) . . . . ?
C7B C12B C11B C10B 0.2(9) . . . . ?
C12B C7B C8B C9B 0.5(7) . . . . ?
C12B C11B C10B C9B -1.5(10) . . . . ?
C11B C10B C9B C8B 2.3(10) . . . . ?
C10B C9B C8B C7B -1.8(8) . . . . ?
C8B C7B C12B C11B 0.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(3)
2 0.2(3)

