# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_230102lu_lgpz291191_0m
_database_code_depnum_ccdc_archive 'CCDC 2234463'
loop_
_audit_author_name
_audit_author_address
'Shikun Jia'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_audit_creation_date             2023-01-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H28 O5'
_chemical_formula_sum            'C31 H28 O5'
_chemical_formula_weight         480.53
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0389 0.0241 '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                   9.1413(5)
_cell_length_b                   12.3151(7)
_cell_length_c                   11.0137(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.512(2)
_cell_angle_gamma                90
_cell_volume                     1238.69(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      60.12
_cell_measurement_theta_min      3.49
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1140 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.9008.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21076
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.365
_diffrn_reflns_theta_min         3.495
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                4996
_reflns_number_total             5470
_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 (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 2178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5470
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.058
_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)+(0.0413P)²+0.0980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0825
_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:
 C24(H24), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C25(H25A,H25B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C23(H23), C27(H27), C8(H8), C28(H28), C22(H22), C19(H19),
 C9(H9), C1(H1), C5(H5), C3(H3A), C21(H21), C20(H20), C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O3 O 0.25796(15) 0.59696(11) 0.67516(12) 0.0464(3) Uani 1 1 d . . . . .
H3 H 0.310925 0.652721 0.676191 0.070 Uiso 1 1 calc R U . . .
O4 O 0.16419(16) 0.31792(11) 0.69368(13) 0.0519(3) Uani 1 1 d . . . . .
O5 O -0.00188(19) 0.71164(13) 0.85711(15) 0.0641(4) Uani 1 1 d . . . . .
O2 O 0.48744(19) 0.66121(12) 0.78760(16) 0.0651(4) Uani 1 1 d . . . . .
O1 O 0.53603(17) 0.28908(12) 0.50397(16) 0.0619(4) Uani 1 1 d . . . . .
C31 C 0.2398(2) 0.37113(17) 0.59991(17) 0.0478(4) Uani 1 1 d . . . . .
H31A H 0.175315 0.426497 0.560324 0.057 Uiso 1 1 calc R U . . .
H31B H 0.266253 0.317564 0.537538 0.057 Uiso 1 1 calc R U . . .
C7 C 0.9780(2) 0.47550(16) 0.35011(15) 0.0426(4) Uani 1 1 d . . . . .
C12 C 0.9463(2) 0.36813(16) 0.38054(16) 0.0429(4) Uani 1 1 d . . . . .
H12 H 1.017287 0.313142 0.369285 0.051 Uiso 1 1 calc R U . . .
C11 C 0.8132(2) 0.34087(16) 0.42671(16) 0.0428(4) Uani 1 1 d . . . . .
H11 H 0.793612 0.267297 0.446199 0.051 Uiso 1 1 calc R U . . .
C26 C 0.0285(2) 0.61745(17) 0.83514(18) 0.0487(5) Uani 1 1 d . . . . .
C17 C 0.4646(2) 0.56566(15) 0.81018(17) 0.0428(4) Uani 1 1 d . . . . .
C6 C 1.1219(2) 0.50415(17) 0.30096(16) 0.0462(4) Uani 1 1 d . . . . .
C24 C 0.2225(2) 0.46783(15) 0.83575(15) 0.0409(4) Uani 1 1 d . . . . .
H24 H 0.281805 0.424319 0.896690 0.049 Uiso 1 1 calc R U . . .
C18 C 0.5646(2) 0.50796(16) 0.89892(16) 0.0414(4) Uani 1 1 d . . . . .
C15 C 0.3774(2) 0.42502(15) 0.65339(16) 0.0410(4) Uani 1 1 d . . . . .
H15 H 0.435654 0.369085 0.700237 0.049 Uiso 1 1 calc R U . . .
C16 C 0.3297(2) 0.51335(14) 0.74339(15) 0.0397(4) Uani 1 1 d . . . . .
C23 C 0.5605(2) 0.39723(17) 0.92342(17) 0.0481(4) Uani 1 1 d . . . . .
H23 H 0.491260 0.352168 0.880874 0.058 Uiso 1 1 calc R U . . .
C13 C 0.5681(2) 0.38545(17) 0.50019(17) 0.0466(4) Uani 1 1 d . . . . .
C29 C 0.1035(2) 0.39167(16) 0.77973(17) 0.0462(4) Uani 1 1 d . . . . .
C25 C 0.1503(2) 0.55972(16) 0.90505(17) 0.0463(4) Uani 1 1 d . . . . .
H25A H 0.110927 0.529386 0.980205 0.056 Uiso 1 1 calc R U . . .
H25B H 0.226352 0.613585 0.929570 0.056 Uiso 1 1 calc R U . . .
C10 C 0.7074(2) 0.41979(15) 0.44513(15) 0.0419(4) Uani 1 1 d . . . . .
C27 C -0.0571(2) 0.55390(19) 0.74517(19) 0.0550(5) Uani 1 1 d . . . . .
H27 H -0.140015 0.586001 0.704399 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8710(2) 0.55404(16) 0.36734(17) 0.0462(4) Uani 1 1 d . . . . .
H8 H 0.889494 0.627356 0.346047 0.055 Uiso 1 1 calc R U . . .
C14 C 0.4729(2) 0.47095(17) 0.55527(17) 0.0469(4) Uani 1 1 d . . . . .
H14A H 0.409215 0.503960 0.490300 0.056 Uiso 1 1 calc R U . . .
H14B H 0.536135 0.528972 0.591101 0.056 Uiso 1 1 calc R U . . .
C28 C -0.0214(2) 0.4525(2) 0.71933(19) 0.0557(5) Uani 1 1 d . . . . .
H28 H -0.079047 0.415806 0.658274 0.067 Uiso 1 1 calc R U . . .
C22 C 0.6577(2) 0.3525(2) 1.01007(19) 0.0591(6) Uani 1 1 d . . . . .
H22 H 0.655518 0.276705 1.025874 0.071 Uiso 1 1 calc R U . . .
C19 C 0.6690(2) 0.57199(19) 0.96225(18) 0.0524(5) Uani 1 1 d . . . . .
H19 H 0.674484 0.647502 0.945441 0.063 Uiso 1 1 calc R U . . .
C9 C 0.7378(2) 0.52684(16) 0.41509(17) 0.0457(4) Uani 1 1 d . . . . .
H9 H 0.666964 0.581762 0.427339 0.055 Uiso 1 1 calc R U . . .
C30 C 0.0461(3) 0.3171(2) 0.8780(2) 0.0636(6) Uani 1 1 d . . . . .
H30A H -0.031607 0.270592 0.842530 0.095 Uiso 1 1 calc R U . . .
H30B H 0.006822 0.361135 0.943164 0.095 Uiso 1 1 calc R U . . .
H30C H 0.126235 0.271689 0.911371 0.095 Uiso 1 1 calc R U . . .
C1 C 1.1804(3) 0.6079(2) 0.3163(2) 0.0584(5) Uani 1 1 d . . . . .
H1 H 1.126754 0.661805 0.357137 0.070 Uiso 1 1 calc R U . . .
C5 C 1.2040(2) 0.4271(2) 0.24018(19) 0.0582(5) Uani 1 1 d . . . . .
H5 H 1.166034 0.356011 0.227664 0.070 Uiso 1 1 calc R U . . .
C3 C 1.3958(3) 0.5562(3) 0.2139(2) 0.0748(8) Uani 1 1 d . . . . .
H3A H 1.488950 0.573809 0.184350 0.090 Uiso 1 1 calc R U . . .
C21 C 0.7575(3) 0.4177(2) 1.07341(19) 0.0665(7) Uani 1 1 d . . . . .
H21 H 0.821910 0.386984 1.134154 0.080 Uiso 1 1 calc R U . . .
C20 C 0.7639(3) 0.5265(2) 1.0488(2) 0.0645(6) Uani 1 1 d . . . . .
H20 H 0.833940 0.570893 1.091447 0.077 Uiso 1 1 calc R U . . .
C2 C 1.3162(3) 0.6335(3) 0.2725(2) 0.0720(7) Uani 1 1 d . . . . .
H2 H 1.354543 0.704748 0.283092 0.086 Uiso 1 1 calc R U . . .
C4 C 1.3398(3) 0.4533(3) 0.1981(2) 0.0716(7) Uani 1 1 d . . . . .
H4 H 1.394911 0.399756 0.158058 0.086 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
O3 H3 0.8400 . ?
O3 C16 1.419(2) . ?
O4 C31 1.427(2) . ?
O4 C29 1.441(2) . ?
O5 C26 1.219(3) . ?
O2 C17 1.223(2) . ?
O1 C13 1.224(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C15 1.518(3) . ?
C7 C12 1.398(3) . ?
C7 C6 1.487(3) . ?
C7 C8 1.395(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.380(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.393(3) . ?
C26 C25 1.504(3) . ?
C26 C27 1.462(3) . ?
C17 C18 1.489(3) . ?
C17 C16 1.548(2) . ?
C6 C1 1.393(3) . ?
C6 C5 1.398(3) . ?
C24 H24 1.0000 . ?
C24 C16 1.548(3) . ?
C24 C29 1.544(3) . ?
C24 C25 1.531(3) . ?
C18 C23 1.391(3) . ?
C18 C19 1.400(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.547(2) . ?
C15 C14 1.527(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.389(3) . ?
C13 C10 1.495(3) . ?
C13 C14 1.510(3) . ?
C29 C28 1.497(3) . ?
C29 C30 1.530(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C10 C9 1.390(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.325(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C28 H28 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.381(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(3) . ?
C9 H9 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.382(3) . ?
C3 H3A 0.9500 . ?
C3 C2 1.376(4) . ?
C3 C4 1.374(4) . ?
C21 H21 0.9500 . ?
C21 C20 1.369(4) . ?
C20 H20 0.9500 . ?
C2 H2 0.9500 . ?
C4 H4 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
C16 O3 H3 109.5 . . ?
C31 O4 C29 113.53(15) . . ?
O4 C31 H31A 109.7 . . ?
O4 C31 H31B 109.7 . . ?
O4 C31 C15 109.84(14) . . ?
H31A C31 H31B 108.2 . . ?
C15 C31 H31A 109.7 . . ?
C15 C31 H31B 109.7 . . ?
C12 C7 C6 120.52(17) . . ?
C8 C7 C12 118.00(18) . . ?
C8 C7 C6 121.48(18) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.92(17) . . ?
C11 C12 H12 119.5 . . ?
C12 C11 H11 119.6 . . ?
C12 C11 C10 120.87(18) . . ?
C10 C11 H11 119.6 . . ?
O5 C26 C25 121.2(2) . . ?
O5 C26 C27 121.6(2) . . ?
C27 C26 C25 117.13(18) . . ?
O2 C17 C18 119.18(17) . . ?
O2 C17 C16 116.31(16) . . ?
C18 C17 C16 124.51(15) . . ?
C1 C6 C7 120.98(19) . . ?
C1 C6 C5 118.0(2) . . ?
C5 C6 C7 121.02(19) . . ?
C16 C24 H24 107.1 . . ?
C29 C24 H24 107.1 . . ?
C29 C24 C16 114.37(14) . . ?
C25 C24 H24 107.1 . . ?
C25 C24 C16 111.05(15) . . ?
C25 C24 C29 109.69(15) . . ?
C23 C18 C17 125.05(17) . . ?
C23 C18 C19 118.61(18) . . ?
C19 C18 C17 116.33(17) . . ?
C31 C15 H15 108.2 . . ?
C31 C15 C16 107.69(15) . . ?
C31 C15 C14 112.15(15) . . ?
C16 C15 H15 108.2 . . ?
C14 C15 H15 108.2 . . ?
C14 C15 C16 112.26(15) . . ?
O3 C16 C17 106.85(14) . . ?
O3 C16 C24 108.62(15) . . ?
O3 C16 C15 107.92(14) . . ?
C17 C16 C24 110.64(14) . . ?
C15 C16 C17 110.85(15) . . ?
C15 C16 C24 111.76(14) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
O1 C13 C10 119.86(19) . . ?
O1 C13 C14 121.30(18) . . ?
C10 C13 C14 118.79(17) . . ?
O4 C29 C24 111.16(15) . . ?
O4 C29 C28 109.33(16) . . ?
O4 C29 C30 103.93(16) . . ?
C28 C29 C24 112.58(17) . . ?
C28 C29 C30 109.64(18) . . ?
C30 C29 C24 109.85(17) . . ?
C26 C25 C24 114.82(15) . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C24 C25 H25A 108.6 . . ?
C24 C25 H25B 108.6 . . ?
H25A C25 H25B 107.5 . . ?
C11 C10 C13 118.11(17) . . ?
C9 C10 C11 118.65(18) . . ?
C9 C10 C13 123.21(18) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.37(19) . . ?
C28 C27 H27 119.3 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.08(19) . . ?
C9 C8 H8 119.5 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 C15 112.54(16) . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C29 C28 H28 117.8 . . ?
C27 C28 C29 124.49(19) . . ?
C27 C28 H28 117.8 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.8 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.46(18) . . ?
C8 C9 H9 119.8 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 119.9 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?

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
O4 C31 C15 C16 -63.3(2) . . . . ?
O4 C31 C15 C14 172.73(15) . . . . ?
O4 C29 C28 C27 -147.1(2) . . . . ?
O5 C26 C25 C24 -152.97(19) . . . . ?
O5 C26 C27 C28 178.2(2) . . . . ?
O2 C17 C18 C23 -173.0(2) . . . . ?
O2 C17 C18 C19 7.6(3) . . . . ?
O2 C17 C16 O3 -3.9(2) . . . . ?
O2 C17 C16 C24 -122.00(19) . . . . ?
O2 C17 C16 C15 113.4(2) . . . . ?
O1 C13 C10 C11 -15.4(3) . . . . ?
O1 C13 C10 C9 166.61(19) . . . . ?
O1 C13 C14 C15 22.8(3) . . . . ?
C31 O4 C29 C24 -55.1(2) . . . . ?
C31 O4 C29 C28 69.8(2) . . . . ?
C31 O4 C29 C30 -173.23(16) . . . . ?
C31 C15 C16 O3 -68.12(18) . . . . ?
C31 C15 C16 C17 175.18(14) . . . . ?
C31 C15 C16 C24 51.25(19) . . . . ?
C31 C15 C14 C13 -81.7(2) . . . . ?
C7 C12 C11 C10 -0.5(3) . . . . ?
C7 C6 C1 C2 178.60(19) . . . . ?
C7 C6 C5 C4 -177.9(2) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C12 C7 C6 C1 -153.38(19) . . . . ?
C12 C7 C6 C5 25.3(3) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C12 C11 C10 C13 -177.52(16) . . . . ?
C12 C11 C10 C9 0.5(3) . . . . ?
C11 C10 C9 C8 0.2(3) . . . . ?
C26 C27 C28 C29 2.0(4) . . . . ?
C17 C18 C23 C22 -178.73(18) . . . . ?
C17 C18 C19 C20 178.21(19) . . . . ?
C6 C7 C12 C11 179.70(16) . . . . ?
C6 C7 C8 C9 -178.95(16) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C5 C4 C3 -0.9(4) . . . . ?
C24 C29 C28 C27 -23.1(3) . . . . ?
C18 C17 C16 O3 175.48(16) . . . . ?
C18 C17 C16 C24 57.4(2) . . . . ?
C18 C17 C16 C15 -67.2(2) . . . . ?
C18 C23 C22 C21 0.8(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C16 C17 C18 C23 7.7(3) . . . . ?
C16 C17 C18 C19 -171.75(17) . . . . ?
C16 C24 C29 O4 42.5(2) . . . . ?
C16 C24 C29 C28 -80.5(2) . . . . ?
C16 C24 C29 C30 157.02(17) . . . . ?
C16 C24 C25 C26 77.6(2) . . . . ?
C16 C15 C14 C13 156.86(15) . . . . ?
C23 C18 C19 C20 -1.2(3) . . . . ?
C23 C22 C21 C20 -1.7(3) . . . . ?
C13 C10 C9 C8 178.17(17) . . . . ?
C29 O4 C31 C15 67.5(2) . . . . ?
C29 C24 C16 O3 76.35(19) . . . . ?
C29 C24 C16 C17 -166.66(15) . . . . ?
C29 C24 C16 C15 -42.6(2) . . . . ?
C29 C24 C25 C26 -49.8(2) . . . . ?
C25 C26 C27 C28 -5.4(3) . . . . ?
C25 C24 C16 O3 -48.44(18) . . . . ?
C25 C24 C16 C17 68.55(18) . . . . ?
C25 C24 C16 C15 -167.40(14) . . . . ?
C25 C24 C29 O4 168.06(15) . . . . ?
C25 C24 C29 C28 45.0(2) . . . . ?
C25 C24 C29 C30 -77.5(2) . . . . ?
C10 C13 C14 C15 -154.49(16) . . . . ?
C27 C26 C25 C24 30.6(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C8 C7 C6 C1 26.6(3) . . . . ?
C8 C7 C6 C5 -154.74(19) . . . . ?
C14 C15 C16 O3 55.81(19) . . . . ?
C14 C15 C16 C17 -60.88(19) . . . . ?
C14 C15 C16 C24 175.19(15) . . . . ?
C14 C13 C10 C11 161.85(16) . . . . ?
C14 C13 C10 C9 -16.1(3) . . . . ?
C22 C21 C20 C19 1.2(4) . . . . ?
C19 C18 C23 C22 0.7(3) . . . . ?
C30 C29 C28 C27 99.5(3) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C5 C6 C1 C2 -0.1(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
####################################################################### 
# 
# 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_20230356
_database_code_depnum_ccdc_archive 'CCDC 2266697'
loop_
_audit_author_name
_audit_author_address
'Shikun Jia'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_audit_creation_date             2023-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 O4'
_chemical_formula_sum            'C25 H24 O4'
_chemical_formula_weight         388.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N3O4
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.5167(2)
_cell_length_b                   14.0635(4)
_cell_length_c                   17.0011(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2036.30(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5160
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3830
_cell_measurement_theta_min      4.0700
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13668
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.457
_diffrn_reflns_theta_min         4.080
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -12.00   1.00    1.00    --  -33.50 -37.00 150.00   91
  2  ω   -108.00 -77.00   1.00    1.00    --  -33.50 178.00 -30.00   31
  3  ω     61.00  91.00   1.00    1.00    --   36.47 178.00-120.00   30
  4  ω     61.00 102.00   1.00    1.00    --   36.47 178.00  30.00   41
  5  ω     75.00 101.00   1.00    1.00    --   36.47 178.00   0.00   26
  6  ω     90.00 142.00   1.00    4.00    --  108.00  45.00-180.00   52
  7  ω    104.00 140.00   1.00    4.00    --  108.00  61.00 -30.00   36
  8  ω    108.00 170.00   1.00    4.00    --  108.00 111.00   0.00   62
  9  ω     53.00  82.00   1.00    4.00    --  108.00-111.00   0.00   29
 10  ω     47.00 107.00   1.00    4.00    --  108.00 -94.00  30.00   60
 11  ω    111.00 173.00   1.00    4.00    --  108.00  77.00 -90.00   62
 12  ω    -71.00 -42.00   1.00    2.00    --  -33.50 178.00 -90.00   29
 13  ω   -107.00 -81.00   1.00    2.00    --  -33.50 178.00 -90.00   26
 14  ω    -37.00  -9.00   1.00    2.00    --  -33.50   0.00   0.00   28
 15  ω      2.00  28.00   1.00    2.00    --  -33.50   0.00   0.00   26
 16  ω     52.00  78.00   1.00    4.00    --  108.00 -94.00   0.00   26
 17  ω     42.00 105.00   1.00    4.00    --  108.00-111.00-150.00   63
 18  ω    122.00 148.00   1.00    4.00    --  108.00  30.00 -30.00   26
 19  ω     38.00 101.00   1.00    4.00    --  108.00 -30.00 -30.00   63
 20  ω    102.00 128.00   1.00    4.00    --  108.00 -30.00 -30.00   26
 21  ω     85.00 111.00   1.00    4.00    --  108.00  30.00 -30.00   26
 22  ω    -88.00 -62.00   1.00    2.00    --  -33.50 -57.00 150.00   26
 23  ω    -37.00 -11.00   1.00    1.50    --  -33.50  57.00-180.00   26
 24  ω    151.00 176.00   1.00    4.00    --  108.00 111.00  60.00   25
 25  ω    101.00 127.00   1.00    4.00    --  108.00 -77.00   0.00   26
 26  ω     90.00 122.00   1.00    4.00    --  108.00  61.00  30.00   32
 27  ω    126.00 152.00   1.00    4.00    --  108.00  61.00  30.00   26
 28  ω     40.00  66.00   1.00    4.00    --  108.00 -77.00   0.00   26
 29  ω    128.00 164.00   1.00    4.00    --  108.00  45.00 150.00   36
 30  ω     70.00 109.00   1.00    4.00    --  108.00 178.00   0.00   39
 31  ω     38.00  72.00   1.00    4.00    --  108.00 -94.00 150.00   34
 32  ω     44.00  70.00   1.00    4.00    --  108.00-111.00   0.00   26
 33  ω    115.00 140.00   1.00    4.00    --  108.00 178.00 -90.00   25
 34  ω    104.00 130.00   1.00    4.00    --  108.00 111.00  60.00   26
 35  ω     97.00 125.00   1.00    4.00    --  108.00 -45.00-120.00   28
 36  ω     74.00 100.00   1.00    4.00    --  108.00  15.00   0.00   26
 37  ω    -37.00 -11.00   1.00    1.50    --  -33.50  57.00-180.00   26
 38  ω    110.00 158.00   1.00    4.00    --  108.00  61.00-120.00   48
 39  ω     48.00  88.00   1.00    4.00    --  108.00 -30.00   0.00   40
 40  ω     87.00 113.00   1.00    4.00    --  108.00  37.00-140.00   26
 41  ω     53.00  60.00   1.00    4.00    --  108.00 -94.00 120.00    7
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0666897000
_diffrn_orient_matrix_UB_12      0.0492543000
_diffrn_orient_matrix_UB_13      0.0737081000
_diffrn_orient_matrix_UB_21      -0.0521203000
_diffrn_orient_matrix_UB_22      -0.0850811000
_diffrn_orient_matrix_UB_23      0.0507548000
_diffrn_orient_matrix_UB_31      0.1599559000
_diffrn_orient_matrix_UB_32      -0.0482111000
_diffrn_orient_matrix_UB_33      -0.0142130000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3468
_reflns_number_total             3872
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.41(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.047
_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)+(0.0648P)²+0.1198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1152
_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:
 C7(H7), C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C6(H6A,H6B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C21(H21), C15(H15), C16(H16), C18(H18), C17(H17), C8(H8), C24(H24),
 C9(H9), C23(H23), C22(H22), C25(H25)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.5321(2) 0.49657(11) 0.20078(10) 0.0459(4) Uani 1 1 d . . . . .
O1 O 0.2249(3) 0.39082(13) 0.31914(13) 0.0638(5) Uani 1 1 d . . . . .
O3 O 0.4294(3) 0.64320(17) 0.12154(17) 0.0780(7) Uani 1 1 d . . . . .
C14 C 0.1567(3) 0.62677(17) 0.13705(15) 0.0486(5) Uani 1 1 d . . . . .
C19 C 0.1330(4) 0.6999(2) 0.08322(16) 0.0568(7) Uani 1 1 d . . . . .
H19 H 0.2191 0.7287 0.0594 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3245(3) 0.59912(18) 0.15266(17) 0.0516(6) Uani 1 1 d . . . . .
C4 C 0.3686(3) 0.51586(17) 0.20835(15) 0.0451(5) Uani 1 1 d . . . . .
C21 C 0.7682(4) 0.3572(2) 0.20271(19) 0.0607(7) Uani 1 1 d . . . . .
H21 H 0.7272 0.3793 0.2500 0.073 Uiso 1 1 calc R . . . .
C11 C 0.4600(4) 0.61856(19) 0.32184(18) 0.0627(7) Uani 1 1 d . . . . .
H11A H 0.4866 0.6605 0.2786 0.075 Uiso 1 1 calc R . . . .
H11B H 0.4154 0.6574 0.3633 0.075 Uiso 1 1 calc R . . . .
C6 C 0.3999(3) 0.3880(2) 0.11693(16) 0.0567(6) Uani 1 1 d . . . . .
H6A H 0.3532 0.4025 0.0663 0.068 Uiso 1 1 calc R . . . .
H6B H 0.4191 0.3202 0.1201 0.068 Uiso 1 1 calc R . . . .
C7 C 0.5539(3) 0.44442(18) 0.12866(15) 0.0502(6) Uani 1 1 d . . . . .
H7 H 0.5652 0.4899 0.0853 0.060 Uiso 1 1 calc R . . . .
C15 C 0.0252(3) 0.58653(19) 0.17293(18) 0.0570(6) Uani 1 1 d . . . . .
H15 H 0.0381 0.5382 0.2097 0.068 Uiso 1 1 calc R . . . .
C20 C 0.6995(3) 0.38400(17) 0.13261(17) 0.0519(6) Uani 1 1 d . . . . .
C5 C 0.2936(3) 0.42061(17) 0.18369(16) 0.0491(6) Uani 1 1 d . . . . .
H5 H 0.1855 0.4297 0.1654 0.059 Uiso 1 1 calc R . . . .
C16 C -0.1245(3) 0.6179(2) 0.1543(2) 0.0626(7) Uani 1 1 d . . . . .
H16 H -0.2115 0.5905 0.1784 0.075 Uiso 1 1 calc R . . . .
C1 C 0.3003(4) 0.35202(18) 0.25217(17) 0.0544(6) Uani 1 1 d . . . . .
H1A H 0.2495 0.2929 0.2376 0.065 Uiso 1 1 calc R . . . .
H1B H 0.4090 0.3382 0.2647 0.065 Uiso 1 1 calc R . . . .
C2 C 0.3123(4) 0.46682(19) 0.35334(18) 0.0614(7) Uani 1 1 d . . . . .
C3 C 0.3341(3) 0.54864(17) 0.29352(16) 0.0507(6) Uani 1 1 d . . . . .
H3 H 0.2348 0.5838 0.2920 0.061 Uiso 1 1 calc R . . . .
C18 C -0.0161(4) 0.7303(2) 0.06479(19) 0.0691(8) Uani 1 1 d . . . . .
H18 H -0.0302 0.7788 0.0282 0.083 Uiso 1 1 calc R . . . .
C10 C 0.6082(5) 0.5743(3) 0.35197(19) 0.0725(9) Uani 1 1 d . . . . .
C17 C -0.1444(4) 0.6893(2) 0.1002(2) 0.0668(8) Uani 1 1 d . . . . .
H17 H -0.2449 0.7100 0.0876 0.080 Uiso 1 1 calc R . . . .
C8 C 0.4656(5) 0.4302(2) 0.38487(18) 0.0715(9) Uani 1 1 d . . . . .
H8 H 0.4673 0.3689 0.4055 0.086 Uiso 1 1 calc R . . . .
O4 O 0.7313(4) 0.6180(2) 0.3521(2) 0.1055(10) Uani 1 1 d . . . . .
C24 C 0.8921(5) 0.2914(3) 0.0640(3) 0.0895(12) Uani 1 1 d . . . . .
H24 H 0.9337 0.2692 0.0169 0.107 Uiso 1 1 calc R . . . .
C9 C 0.5976(5) 0.4787(3) 0.3853(2) 0.0776(10) Uani 1 1 d . . . . .
H9 H 0.6867 0.4515 0.4074 0.093 Uiso 1 1 calc R . . . .
C23 C 0.9588(4) 0.2645(2) 0.1337(3) 0.0831(11) Uani 1 1 d . . . . .
H23 H 1.0451 0.2240 0.1340 0.100 Uiso 1 1 calc R . . . .
C22 C 0.8976(4) 0.2977(2) 0.2032(3) 0.0722(9) Uani 1 1 d . . . . .
H22 H 0.9432 0.2801 0.2507 0.087 Uiso 1 1 calc R . . . .
C25 C 0.7628(4) 0.3514(3) 0.0629(2) 0.0734(9) Uani 1 1 d . . . . .
H25 H 0.7188 0.3698 0.0152 0.088 Uiso 1 1 calc R . . . .
C12 C 0.2102(6) 0.5007(3) 0.4221(2) 0.0983(14) Uani 1 1 d . . . . .
H12A H 0.2004 0.4505 0.4600 0.148 Uiso 1 1 calc GR . . . .
H12B H 0.1081 0.5178 0.4029 0.148 Uiso 1 1 calc GR . . . .
H12C H 0.2583 0.5550 0.4464 0.148 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C4 1.425(3) . ?
O2 C7 1.441(3) . ?
O1 C1 1.417(4) . ?
O1 C2 1.427(4) . ?
O3 C13 1.209(3) . ?
C14 C19 1.392(4) . ?
C14 C13 1.504(4) . ?
C14 C15 1.395(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.377(5) . ?
C13 C4 1.552(3) . ?
C4 C5 1.542(3) . ?
C4 C3 1.548(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.380(4) . ?
C21 C22 1.384(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C3 1.533(4) . ?
C11 C10 1.497(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.545(4) . ?
C6 C5 1.522(4) . ?
C7 H7 0.9800 . ?
C7 C20 1.505(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C20 C25 1.380(4) . ?
C5 H5 0.9800 . ?
C5 C1 1.513(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.547(4) . ?
C2 C8 1.503(5) . ?
C2 C12 1.532(5) . ?
C3 H3 0.9800 . ?
C18 H18 0.9300 . ?
C18 C17 1.374(5) . ?
C10 O4 1.215(4) . ?
C10 C9 1.461(5) . ?
C17 H17 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.315(5) . ?
C24 H24 0.9300 . ?
C24 C23 1.368(7) . ?
C24 C25 1.388(5) . ?
C9 H9 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.373(6) . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C7 107.45(18) . . ?
C1 O1 C2 112.3(2) . . ?
C19 C14 C13 116.4(2) . . ?
C19 C14 C15 118.1(3) . . ?
C15 C14 C13 125.5(2) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
O3 C13 C14 119.5(2) . . ?
O3 C13 C4 118.3(2) . . ?
C14 C13 C4 122.2(2) . . ?
O2 C4 C13 109.0(2) . . ?
O2 C4 C5 102.39(19) . . ?
O2 C4 C3 109.1(2) . . ?
C5 C4 C13 112.9(2) . . ?
C5 C4 C3 115.8(2) . . ?
C3 C4 C13 107.5(2) . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(3) . . ?
C22 C21 H21 119.7 . . ?
H11A C11 H11B 107.5 . . ?
C3 C11 H11A 108.4 . . ?
C3 C11 H11B 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C3 115.5(2) . . ?
H6A C6 H6B 108.9 . . ?
C7 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
C5 C6 C7 104.7(2) . . ?
O2 C7 C6 105.2(2) . . ?
O2 C7 H7 108.7 . . ?
O2 C7 C20 110.8(2) . . ?
C6 C7 H7 108.7 . . ?
C20 C7 C6 114.5(2) . . ?
C20 C7 H7 108.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C21 C20 C7 122.8(2) . . ?
C25 C20 C21 119.0(3) . . ?
C25 C20 C7 118.1(3) . . ?
C4 C5 H5 111.2 . . ?
C6 C5 C4 102.6(2) . . ?
C6 C5 H5 111.2 . . ?
C1 C5 C4 109.2(2) . . ?
C1 C5 C6 111.1(2) . . ?
C1 C5 H5 111.2 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
O1 C1 C5 110.8(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
C5 C1 H1A 109.5 . . ?
C5 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C3 110.6(2) . . ?
O1 C2 C8 110.0(2) . . ?
O1 C2 C12 104.3(3) . . ?
C8 C2 C3 112.7(2) . . ?
C8 C2 C12 109.1(3) . . ?
C12 C2 C3 109.8(3) . . ?
C4 C3 H3 106.8 . . ?
C11 C3 C4 110.6(2) . . ?
C11 C3 C2 110.8(2) . . ?
C11 C3 H3 106.8 . . ?
C2 C3 C4 114.6(2) . . ?
C2 C3 H3 106.8 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
O4 C10 C11 121.2(3) . . ?
O4 C10 C9 121.2(4) . . ?
C9 C10 C11 117.6(3) . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C2 C8 H8 117.8 . . ?
C9 C8 C2 124.5(3) . . ?
C9 C8 H8 117.8 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C10 C9 H9 119.0 . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H9 119.0 . . ?
C24 C23 H23 120.2 . . ?
C24 C23 C22 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C20 C25 C24 120.0(4) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O2 C4 C5 C6 -37.8(2) . . . . ?
O2 C4 C5 C1 80.1(2) . . . . ?
O2 C4 C3 C11 42.8(3) . . . . ?
O2 C4 C3 C2 -83.2(3) . . . . ?
O2 C7 C20 C21 20.8(4) . . . . ?
O2 C7 C20 C25 -161.6(3) . . . . ?
O1 C2 C3 C4 -40.0(3) . . . . ?
O1 C2 C3 C11 -166.0(2) . . . . ?
O1 C2 C8 C9 146.2(3) . . . . ?
O3 C13 C4 O2 -10.4(4) . . . . ?
O3 C13 C4 C5 -123.5(3) . . . . ?
O3 C13 C4 C3 107.6(3) . . . . ?
C14 C19 C18 C17 0.8(5) . . . . ?
C14 C13 C4 O2 170.1(2) . . . . ?
C14 C13 C4 C5 57.1(3) . . . . ?
C14 C13 C4 C3 -71.8(3) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C19 C14 C13 O3 3.3(4) . . . . ?
C19 C14 C13 C4 -177.2(2) . . . . ?
C19 C14 C15 C16 1.0(4) . . . . ?
C19 C18 C17 C16 0.1(5) . . . . ?
C13 C14 C19 C18 179.9(3) . . . . ?
C13 C14 C15 C16 179.7(3) . . . . ?
C13 C4 C5 C6 79.2(2) . . . . ?
C13 C4 C5 C1 -162.9(2) . . . . ?
C13 C4 C3 C11 -75.2(3) . . . . ?
C13 C4 C3 C2 158.8(2) . . . . ?
C4 O2 C7 C6 -29.9(2) . . . . ?
C4 O2 C7 C20 -154.2(2) . . . . ?
C4 C5 C1 O1 56.8(3) . . . . ?
C21 C20 C25 C24 1.1(5) . . . . ?
C11 C10 C9 C8 4.1(5) . . . . ?
C6 C7 C20 C21 -98.0(3) . . . . ?
C6 C7 C20 C25 79.6(3) . . . . ?
C6 C5 C1 O1 169.3(2) . . . . ?
C7 O2 C4 C13 -77.1(2) . . . . ?
C7 O2 C4 C5 42.7(2) . . . . ?
C7 O2 C4 C3 165.86(18) . . . . ?
C7 C6 C5 C4 19.9(2) . . . . ?
C7 C6 C5 C1 -96.6(2) . . . . ?
C7 C20 C25 C24 -176.6(3) . . . . ?
C15 C14 C19 C18 -1.3(4) . . . . ?
C15 C14 C13 O3 -175.4(3) . . . . ?
C15 C14 C13 C4 4.0(4) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C5 C4 C3 C11 157.6(2) . . . . ?
C5 C4 C3 C2 31.5(3) . . . . ?
C5 C6 C7 O2 4.4(2) . . . . ?
C5 C6 C7 C20 126.3(2) . . . . ?
C1 O1 C2 C3 60.3(3) . . . . ?
C1 O1 C2 C8 -64.9(3) . . . . ?
C1 O1 C2 C12 178.2(3) . . . . ?
C2 O1 C1 C5 -71.2(3) . . . . ?
C2 C8 C9 C10 -1.9(6) . . . . ?
C3 C4 C5 C6 -156.4(2) . . . . ?
C3 C4 C5 C1 -38.5(3) . . . . ?
C3 C11 C10 O4 156.1(3) . . . . ?
C3 C11 C10 C9 -27.3(4) . . . . ?
C3 C2 C8 C9 22.3(5) . . . . ?
C10 C11 C3 C4 -82.2(3) . . . . ?
C10 C11 C3 C2 46.0(3) . . . . ?
C8 C2 C3 C4 83.6(3) . . . . ?
C8 C2 C3 C11 -42.4(3) . . . . ?
O4 C10 C9 C8 -179.3(4) . . . . ?
C24 C23 C22 C21 0.6(5) . . . . ?
C23 C24 C25 C20 -0.6(6) . . . . ?
C22 C21 C20 C7 176.8(3) . . . . ?
C22 C21 C20 C25 -0.7(4) . . . . ?
C25 C24 C23 C22 -0.3(6) . . . . ?
C12 C2 C3 C4 -154.6(3) . . . . ?
C12 C2 C3 C11 79.4(4) . . . . ?
C12 C2 C8 C9 -99.9(4) . . . . ?

_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 1.160
_oxdiff_exptl_absorpt_empirical_full_min 0.885
####################################################################### 
# 
# 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_202307177_auto
_database_code_depnum_ccdc_archive 'CCDC 2281199'
loop_
_audit_author_name
_audit_author_address
'Shikun Jia'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-07-13 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_audit_creation_date             2023-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 O5'
_chemical_formula_sum            'C25 H24 O5'
_chemical_formula_weight         404.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H28O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0964(6)
_cell_length_b                   11.2963(8)
_cell_length_c                   12.0978(8)
_cell_angle_alpha                116.586(7)
_cell_angle_beta                 95.901(6)
_cell_angle_gamma                91.924(6)
_cell_volume                     980.27(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5140
_cell_measurement_theta_min      4.1050
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.022
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         4.122
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  60.00   73
  2  ω   -106.00   4.00   1.00    1.00    --  -33.50 -19.00 -90.00  110
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 -60.00   73
  4  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00-150.00   87
  5  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00  90.00   87
  6  ω      0.00  28.00   1.00    1.00    --   36.47  92.00-171.86   28
  7  ω     61.00 110.00   1.00    1.00    --   36.47 178.00-180.00   49
  8  ω     -2.00  25.00   1.00    1.00    --   36.47  95.00 109.46   27
  9  ω     -1.00  26.00   1.00    1.00    --   36.47  94.00 -56.30   27
 10  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00 -30.00   75
 11  ω     38.00 128.00   1.00    4.50    --  108.00 -45.00 -90.00   90
 12  ω     40.00 128.00   1.00    4.50    --  108.00 -61.00 150.00   88
 13  ω     88.00 176.00   1.00    4.50    --  108.00  61.00 -60.00   88
 14  ω     40.00 128.00   1.00    4.50    --  108.00 -61.00 -30.00   88
 15  ω     38.00 106.00   1.00    4.50    --  108.00 -94.00 -60.00   68
 16  ω     83.00 178.00   1.00    4.50    --  108.00  30.00  90.00   95
 17  ω     53.00 127.00   1.00    4.50    --  108.00 -30.00 120.00   74
 18  ω    146.00 172.00   1.00    4.50    --  108.00  61.00 -90.00   26
 19  ω     44.00 109.00   1.00    4.50    --  108.00-111.00  60.00   65
 20  ω     58.00 128.00   1.00    4.50    --  108.00 -45.00  30.00   70
 21  ω     80.00 109.00   1.00    4.50    --  108.00-111.00-120.00   29
 22  ω     96.00 122.00   1.00    4.50    --  108.00  61.00 -90.00   26
 23  ω     65.00 169.00   1.00    4.50    --  108.00  15.00  30.00  104
 24  ω     59.00 103.00   1.00    4.50    --  108.00 -94.00 120.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1742444000
_diffrn_orient_matrix_UB_12      -0.0051257000
_diffrn_orient_matrix_UB_13      -0.0416717000
_diffrn_orient_matrix_UB_21      -0.0243065000
_diffrn_orient_matrix_UB_22      -0.1530099000
_diffrn_orient_matrix_UB_23      -0.0658133000
_diffrn_orient_matrix_UB_31      -0.0770437000
_diffrn_orient_matrix_UB_32      0.0025291000
_diffrn_orient_matrix_UB_33      -0.1206994000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2771
_reflns_number_total             3509
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.037
_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)+(0.0591P)²+0.0615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1287
_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:
 C3(H3), C5(H5), C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.65752(15) 0.22342(13) 0.75242(11) 0.0344(3) Uani 1 1 d . . . . .
O2 O 0.45722(18) 0.37252(15) 0.80316(14) 0.0458(3) Uani 1 1 d . . . . .
H2 H 0.3690 0.3259 0.7839 0.069 Uiso 1 1 calc GR . . . .
O3 O 0.93779(18) 0.18182(15) 1.02693(13) 0.0439(3) Uani 1 1 d . . . . .
O4 O 1.08728(18) 0.28299(16) 0.76705(14) 0.0515(4) Uani 1 1 d . . . . .
O5 O 0.68278(19) -0.07167(16) 0.96600(15) 0.0518(4) Uani 1 1 d . . . . .
C1 C 0.5788(2) 0.32048(19) 0.85455(18) 0.0382(4) Uani 1 1 d . . . . .
C2 C 0.7238(3) 0.42106(19) 0.93156(19) 0.0407(4) Uani 1 1 d . . . . .
H2A H 0.6976 0.4816 1.0135 0.049 Uiso 1 1 calc R . . . .
H2B H 0.7605 0.4714 0.8900 0.049 Uiso 1 1 calc R . . . .
C3 C 0.8517(2) 0.32801(19) 0.93858(17) 0.0367(4) Uani 1 1 d . . . . .
H3 H 0.9657 0.3711 0.9622 0.044 Uiso 1 1 calc R . . . .
C4 C 0.8087(2) 0.2651(2) 1.02253(18) 0.0397(4) Uani 1 1 d . . . . .
C5 C 0.6414(2) 0.1777(2) 0.96397(18) 0.0388(4) Uani 1 1 d . . . . .
H5 H 0.6009 0.1521 1.0245 0.047 Uiso 1 1 calc R . . . .
C6 C 0.5104(2) 0.2544(2) 0.92833(19) 0.0403(4) Uani 1 1 d . . . . .
H6A H 0.4138 0.1937 0.8787 0.048 Uiso 1 1 calc R . . . .
H6B H 0.4746 0.3219 1.0035 0.048 Uiso 1 1 calc R . . . .
C7 C 0.8239(2) 0.21510(18) 0.80243(16) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.8375(2) 0.08021(18) 0.80635(17) 0.0349(4) Uani 1 1 d . . . . .
H8 H 0.8540 0.0094 0.7247 0.042 Uiso 1 1 calc R . . . .
C9 C 0.9808(2) 0.0974(2) 0.90558(18) 0.0394(4) Uani 1 1 d . . . . .
H9A H 1.0039 0.0114 0.9001 0.047 Uiso 1 1 calc R . . . .
H9B H 1.0804 0.1365 0.8920 0.047 Uiso 1 1 calc R . . . .
C10 C 0.6735(2) 0.05078(19) 0.84737(18) 0.0373(4) Uani 1 1 d . . . . .
H10 H 0.5834 0.0348 0.7804 0.045 Uiso 1 1 calc R . . . .
C11 C 0.8052(3) 0.3666(3) 1.15752(19) 0.0541(6) Uani 1 1 d . . . . .
H11A H 0.9036 0.4275 1.1861 0.081 Uiso 1 1 calc GR . . . .
H11B H 0.8016 0.3216 1.2084 0.081 Uiso 1 1 calc GR . . . .
H11C H 0.7083 0.4146 1.1632 0.081 Uiso 1 1 calc GR . . . .
C12 C 0.9476(2) 0.23054(18) 0.72069(18) 0.0364(4) Uani 1 1 d . . . . .
C13 C 0.8925(2) 0.1799(2) 0.58437(18) 0.0395(4) Uani 1 1 d . . . . .
C14 C 0.9656(3) 0.2421(2) 0.5227(2) 0.0519(5) Uani 1 1 d . . . . .
H14 H 1.0476 0.3122 0.5660 0.062 Uiso 1 1 calc R . . . .
C15 C 0.9160(4) 0.1993(3) 0.3967(2) 0.0669(7) Uani 1 1 d . . . . .
H15 H 0.9632 0.2424 0.3561 0.080 Uiso 1 1 calc R . . . .
C16 C 0.7976(3) 0.0936(3) 0.3311(2) 0.0643(7) Uani 1 1 d . . . . .
H16 H 0.7645 0.0659 0.2467 0.077 Uiso 1 1 calc R . . . .
C17 C 0.7279(3) 0.0286(3) 0.3911(2) 0.0573(6) Uani 1 1 d . . . . .
H17 H 0.6508 -0.0448 0.3464 0.069 Uiso 1 1 calc R . . . .
C18 C 0.7731(3) 0.0728(2) 0.5170(2) 0.0463(5) Uani 1 1 d . . . . .
H18 H 0.7234 0.0307 0.5575 0.056 Uiso 1 1 calc R . . . .
C19 C 0.6784(2) -0.0748(2) 0.8641(2) 0.0417(5) Uani 1 1 d . . . . .
C20 C 0.6806(2) -0.2043(2) 0.7495(2) 0.0468(5) Uani 1 1 d . . . . .
C21 C 0.6333(3) -0.2201(2) 0.6294(2) 0.0533(5) Uani 1 1 d . . . . .
H21 H 0.5951 -0.1491 0.6182 0.064 Uiso 1 1 calc R . . . .
C22 C 0.6426(3) -0.3412(3) 0.5260(3) 0.0640(7) Uani 1 1 d . . . . .
H22 H 0.6111 -0.3510 0.4461 0.077 Uiso 1 1 calc R . . . .
C23 C 0.6990(4) -0.4465(3) 0.5430(3) 0.0731(8) Uani 1 1 d . . . . .
H23 H 0.7074 -0.5271 0.4741 0.088 Uiso 1 1 calc R . . . .
C24 C 0.7429(4) -0.4330(3) 0.6611(3) 0.0754(8) Uani 1 1 d . . . . .
H24 H 0.7797 -0.5047 0.6719 0.090 Uiso 1 1 calc R . . . .
C25 C 0.7324(3) -0.3126(2) 0.7644(3) 0.0600(6) Uani 1 1 d . . . . .
H25 H 0.7603 -0.3045 0.8442 0.072 Uiso 1 1 calc R . . . .


_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 1.460(2) . ?
O1 C7 1.442(2) . ?
O2 H2 0.8200 . ?
O2 C1 1.393(2) . ?
O3 C4 1.442(2) . ?
O3 C9 1.435(2) . ?
O4 C12 1.213(2) . ?
O5 C19 1.214(3) . ?
C1 C2 1.508(3) . ?
C1 C6 1.527(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.523(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.536(3) . ?
C3 C7 1.554(3) . ?
C4 C5 1.549(3) . ?
C4 C11 1.522(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.538(3) . ?
C5 C10 1.550(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.553(3) . ?
C7 C12 1.536(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.521(3) . ?
C8 C10 1.541(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C19 1.521(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.494(3) . ?
C13 C14 1.389(3) . ?
C13 C18 1.392(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.501(3) . ?
C20 C21 1.391(3) . ?
C20 C25 1.386(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.391(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.379(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.374(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.388(4) . ?
C25 H25 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
C7 O1 C1 107.74(13) . . ?
C1 O2 H2 109.5 . . ?
C9 O3 C4 112.36(14) . . ?
O1 C1 C2 101.96(15) . . ?
O1 C1 C6 109.55(15) . . ?
O2 C1 O1 107.65(15) . . ?
O2 C1 C2 112.73(17) . . ?
O2 C1 C6 113.55(16) . . ?
C2 C1 C6 110.69(16) . . ?
C1 C2 H2A 111.8 . . ?
C1 C2 H2B 111.8 . . ?
C1 C2 C3 99.73(15) . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2A 111.8 . . ?
C3 C2 H2B 111.8 . . ?
C2 C3 H3 112.1 . . ?
C2 C3 C4 112.21(16) . . ?
C2 C3 C7 101.07(15) . . ?
C4 C3 H3 112.1 . . ?
C4 C3 C7 106.74(15) . . ?
C7 C3 H3 112.1 . . ?
O3 C4 C3 108.70(16) . . ?
O3 C4 C5 108.90(16) . . ?
O3 C4 C11 105.25(16) . . ?
C3 C4 C5 108.37(15) . . ?
C11 C4 C3 113.34(18) . . ?
C11 C4 C5 112.14(18) . . ?
C4 C5 H5 109.1 . . ?
C4 C5 C10 108.22(15) . . ?
C6 C5 C4 110.60(16) . . ?
C6 C5 H5 109.1 . . ?
C6 C5 C10 110.65(15) . . ?
C10 C5 H5 109.1 . . ?
C1 C6 C5 111.80(15) . . ?
C1 C6 H6A 109.3 . . ?
C1 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 C3 105.67(14) . . ?
O1 C7 C8 110.69(14) . . ?
O1 C7 C12 108.84(14) . . ?
C8 C7 C3 108.29(15) . . ?
C12 C7 C3 113.08(15) . . ?
C12 C7 C8 110.20(15) . . ?
C7 C8 H8 111.2 . . ?
C9 C8 C7 108.32(15) . . ?
C9 C8 H8 111.2 . . ?
C9 C8 C10 108.60(16) . . ?
C10 C8 C7 106.08(15) . . ?
C10 C8 H8 111.2 . . ?
O3 C9 C8 109.73(15) . . ?
O3 C9 H9A 109.7 . . ?
O3 C9 H9B 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C5 C10 H10 107.6 . . ?
C8 C10 C5 107.72(15) . . ?
C8 C10 H10 107.6 . . ?
C19 C10 C5 115.28(16) . . ?
C19 C10 C8 110.68(16) . . ?
C19 C10 H10 107.6 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 C7 119.97(17) . . ?
O4 C12 C13 121.21(18) . . ?
C13 C12 C7 118.83(16) . . ?
C14 C13 C12 118.14(19) . . ?
C14 C13 C18 119.05(19) . . ?
C18 C13 C12 122.81(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
O5 C19 C10 121.9(2) . . ?
O5 C19 C20 120.54(19) . . ?
C20 C19 C10 117.52(18) . . ?
C21 C20 C19 123.0(2) . . ?
C25 C20 C19 118.3(2) . . ?
C25 C20 C21 118.7(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.4(3) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?

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
O2 H2 O4 0.82 2.29 3.052(2) 156.0 1_455
C5 H5 O5 0.98 2.47 3.193(2) 130.0 2_657

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 -48.07(17) . . . . ?
O1 C1 C6 C5 49.8(2) . . . . ?
O1 C7 C8 C9 -156.05(14) . . . . ?
O1 C7 C8 C10 -39.62(19) . . . . ?
O1 C7 C12 O4 147.99(18) . . . . ?
O1 C7 C12 C13 -32.1(2) . . . . ?
O2 C1 C2 C3 -163.21(16) . . . . ?
O2 C1 C6 C5 170.14(16) . . . . ?
O3 C4 C5 C6 -166.35(15) . . . . ?
O3 C4 C5 C10 -45.0(2) . . . . ?
O4 C12 C13 C14 -28.8(3) . . . . ?
O4 C12 C13 C18 150.5(2) . . . . ?
O5 C19 C20 C21 162.9(2) . . . . ?
O5 C19 C20 C25 -17.2(3) . . . . ?
C1 O1 C7 C3 -7.75(18) . . . . ?
C1 O1 C7 C8 109.28(16) . . . . ?
C1 O1 C7 C12 -129.48(15) . . . . ?
C1 C2 C3 C4 -71.06(19) . . . . ?
C1 C2 C3 C7 42.32(17) . . . . ?
C2 C1 C6 C5 -61.9(2) . . . . ?
C2 C3 C4 O3 -178.40(15) . . . . ?
C2 C3 C4 C5 63.4(2) . . . . ?
C2 C3 C4 C11 -61.8(2) . . . . ?
C2 C3 C7 O1 -22.20(17) . . . . ?
C2 C3 C7 C8 -140.84(15) . . . . ?
C2 C3 C7 C12 96.75(17) . . . . ?
C3 C4 C5 C6 -48.3(2) . . . . ?
C3 C4 C5 C10 73.09(19) . . . . ?
C3 C7 C8 C9 -40.65(19) . . . . ?
C3 C7 C8 C10 75.78(17) . . . . ?
C3 C7 C12 O4 30.9(3) . . . . ?
C3 C7 C12 C13 -149.21(17) . . . . ?
C4 O3 C9 C8 -22.0(2) . . . . ?
C4 C3 C7 O1 95.25(16) . . . . ?
C4 C3 C7 C8 -23.38(19) . . . . ?
C4 C3 C7 C12 -145.80(15) . . . . ?
C4 C5 C6 C1 48.8(2) . . . . ?
C4 C5 C10 C8 -19.9(2) . . . . ?
C4 C5 C10 C19 104.21(18) . . . . ?
C5 C10 C19 O5 -10.9(3) . . . . ?
C5 C10 C19 C20 170.09(16) . . . . ?
C6 C1 C2 C3 68.39(18) . . . . ?
C6 C5 C10 C8 101.41(17) . . . . ?
C6 C5 C10 C19 -134.47(17) . . . . ?
C7 O1 C1 O2 153.98(14) . . . . ?
C7 O1 C1 C2 35.17(17) . . . . ?
C7 O1 C1 C6 -82.11(17) . . . . ?
C7 C3 C4 O3 71.76(18) . . . . ?
C7 C3 C4 C5 -46.4(2) . . . . ?
C7 C3 C4 C11 -171.60(16) . . . . ?
C7 C8 C9 O3 69.01(19) . . . . ?
C7 C8 C10 C5 -48.80(19) . . . . ?
C7 C8 C10 C19 -175.66(15) . . . . ?
C7 C12 C13 C14 151.32(19) . . . . ?
C7 C12 C13 C18 -29.4(3) . . . . ?
C8 C7 C12 O4 -90.5(2) . . . . ?
C8 C7 C12 C13 89.44(19) . . . . ?
C8 C10 C19 O5 111.7(2) . . . . ?
C8 C10 C19 C20 -67.4(2) . . . . ?
C9 O3 C4 C3 -46.5(2) . . . . ?
C9 O3 C4 C5 71.36(19) . . . . ?
C9 O3 C4 C11 -168.23(16) . . . . ?
C9 C8 C10 C5 67.45(19) . . . . ?
C9 C8 C10 C19 -59.4(2) . . . . ?
C10 C5 C6 C1 -71.1(2) . . . . ?
C10 C8 C9 O3 -45.8(2) . . . . ?
C10 C19 C20 C21 -18.1(3) . . . . ?
C10 C19 C20 C25 161.81(19) . . . . ?
C11 C4 C5 C6 77.6(2) . . . . ?
C11 C4 C5 C10 -161.06(17) . . . . ?
C12 C7 C8 C9 83.51(18) . . . . ?
C12 C7 C8 C10 -160.06(15) . . . . ?
C12 C13 C14 C15 -179.0(2) . . . . ?
C12 C13 C18 C17 -179.2(2) . . . . ?
C13 C14 C15 C16 -1.5(4) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 2.3(4) . . . . ?
C16 C17 C18 C13 -2.1(3) . . . . ?
C18 C13 C14 C15 1.7(3) . . . . ?
C19 C20 C21 C22 177.9(2) . . . . ?
C19 C20 C25 C24 -177.4(2) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C20 C25 C24 2.5(4) . . . . ?
C21 C22 C23 C24 1.2(4) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C23 C24 C25 C20 -1.2(4) . . . . ?
C25 C20 C21 C22 -1.9(3) . . . . ?

_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 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.920
####################################################################### 
# 
# 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_20230206
_database_code_depnum_ccdc_archive 'CCDC 2246355'
loop_
_audit_author_name
_audit_author_address
'Shikun Jia'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-03-05 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_audit_creation_date             2023-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H30 O5'
_chemical_formula_sum            'C28 H30 O5'
_chemical_formula_weight         446.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2I
_chemical_oxdiff_usercomment     r
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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   11.5324(2)
_cell_length_b                   11.5324(2)
_cell_length_c                   14.9982(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1727.46(8)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4979
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8700
_cell_measurement_theta_min      4.4040
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             714
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9585
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.942
_diffrn_reflns_theta_min         4.427
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    2.50    --  -33.50 -57.00 -30.00   87
  2  ω    -26.00  11.00   1.00    2.50    --   36.47 -37.00 -60.00   37
  3  ω     18.00  46.00   1.00    2.50    --   36.47 -37.00 -60.00   28
  4  ω     21.00  75.00   1.00    2.50    --   36.47 -99.00 150.00   54
  5  ω     -3.00  74.00   1.00    2.50    --   36.47 -99.00   0.00   77
  6  ω     18.00  94.00   1.00    2.50    --   36.47  57.00-150.00   76
  7  ω     59.00 104.00   1.00    2.50    --   36.47  37.00 -90.00   45
  8  ω     58.00  87.00   1.00    2.50    --   36.47 178.00 -60.00   29
  9  ω    -31.00  14.00   1.00    2.50    --   36.47 -57.00 -90.00   45
 10  ω     43.00  79.00   1.00    7.50    --  108.00 -94.00 120.00   36
 11  ω     88.00 122.00   1.00    7.50    --  108.00-131.00-107.00   34
 12  ω     73.00 107.00   1.00    7.50    --  108.00 -94.00-120.00   34
 13  ω     39.00  64.00   1.00    7.50    --  108.00-131.00-107.00   25
 14  ω    105.00 178.00   1.00    7.50    --  108.00 111.00 -60.00   73
 15  ω     66.00 109.00   1.00    7.50    --  108.00 -94.00   0.00   43
 16  ω     61.00 119.00   1.00    7.50    --  108.00 -61.00 -90.00   58
 17  ω     79.00 177.00   1.00    7.50    --  108.00  77.00-120.00   98
 18  ω     95.00 159.00   1.00    7.50    --  108.00  61.00   0.00   64
 19  ω     66.00 131.00   1.00    7.50    --  108.00 -30.00-150.00   65
 20  ω     77.00 102.00   1.00    1.50    --   36.47  57.00 -60.00   25
 21  ω     35.00  74.00   1.00    1.50    --   36.47  57.00 -60.00   39
 22  ω     21.00  61.00   1.00    1.50    --   36.47  57.00   0.00   40
 23  ω     78.00 104.00   1.00    1.50    --   36.47 178.00 -30.00   26
 24  ω     -8.00  17.00   1.00    1.50    --   36.47 108.00 -94.71   25
 25  ω     88.00 124.00   1.00    7.50    --  108.00  61.00  30.00   36
 26  ω     79.00 104.00   1.00    7.50    --  108.00  77.00 -30.00   25
 27  ω    147.00 175.00   1.00    7.50    --  108.00  77.00   0.00   28
 28  ω     85.00 110.00   1.00    7.50    --  108.00 -94.00 -90.00   25
 29  ω     84.00 110.00   1.00    7.50    --  108.00  30.00  60.00   26
 30  ω    145.00 157.00   1.00    7.50    --  108.00  45.00  30.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470145000
_diffrn_orient_matrix_UB_12      -0.1211956000
_diffrn_orient_matrix_UB_13      0.0627127000
_diffrn_orient_matrix_UB_21      0.1469505000
_diffrn_orient_matrix_UB_22      0.0414635000
_diffrn_orient_matrix_UB_23      0.0193049000
_diffrn_orient_matrix_UB_31      0.0013169000
_diffrn_orient_matrix_UB_32      0.0859958000
_diffrn_orient_matrix_UB_33      0.0789707000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.840
_reflns_number_gt                3850
_reflns_number_total             4078
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     37.37
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4078
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.043
_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)+(0.0853P)²+0.0601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1280
_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:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C17(H17A,H17B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.8414(3) 1.0927(4) 0.5353(2) 0.0727(9) Uani 1 1 d . . . . .
O2 O 0.7700(2) 0.8142(2) 0.26809(16) 0.0416(5) Uani 1 1 d . . . . .
H2 H 0.8325 0.8561 0.2336 0.062 Uiso 1 1 calc GR . . . .
O3 O 0.5113(2) 0.7471(2) 0.42154(14) 0.0387(5) Uani 1 1 d . . . . .
O4 O 0.5925(4) 0.5609(4) 0.1081(2) 0.0697(8) Uani 1 1 d . . . . .
O5 O 0.8548(3) 1.0219(3) 0.1716(2) 0.0650(8) Uani 1 1 d . . . . .
C1 C 1.1591(4) 1.1585(4) 0.4444(3) 0.0509(8) Uani 1 1 d . . . . .
H1 H 1.1302 1.1124 0.3907 0.061 Uiso 1 1 calc R . . . .
C2 C 1.2940(4) 1.2230(4) 0.4665(3) 0.0624(11) Uani 1 1 d . . . . .
H2A H 1.3550 1.2189 0.4279 0.075 Uiso 1 1 calc R . . . .
C3 C 1.3381(5) 1.2926(5) 0.5448(4) 0.0729(13) Uani 1 1 d . . . . .
H3 H 1.4285 1.3351 0.5595 0.088 Uiso 1 1 calc R . . . .
C4 C 1.2473(6) 1.2993(5) 0.6018(3) 0.0761(14) Uani 1 1 d . . . . .
H4 H 1.2770 1.3476 0.6547 0.091 Uiso 1 1 calc R . . . .
C5 C 1.1128(5) 1.2347(4) 0.5807(3) 0.0600(10) Uani 1 1 d . . . . .
H5 H 1.0524 1.2396 0.6193 0.072 Uiso 1 1 calc R . . . .
C6 C 1.0676(4) 1.1627(3) 0.5020(2) 0.0461(7) Uani 1 1 d . . . . .
C7 C 0.9192(4) 1.0898(3) 0.4825(2) 0.0462(8) Uani 1 1 d . . . . .
C8 C 0.8756(3) 1.0148(3) 0.3958(2) 0.0421(7) Uani 1 1 d . . . . .
H8A H 0.9078 0.9517 0.3939 0.050 Uiso 1 1 calc R . . . .
H8B H 0.9189 1.0783 0.3476 0.050 Uiso 1 1 calc R . . . .
C9 C 0.6518(3) 0.8196(3) 0.4400(2) 0.0405(7) Uani 1 1 d . . . . .
H9A H 0.6882 0.7603 0.4332 0.049 Uiso 1 1 calc R . . . .
H9B H 0.6659 0.8508 0.5012 0.049 Uiso 1 1 calc R . . . .
C10 C 0.7246(3) 0.9381(3) 0.37795(19) 0.0366(6) Uani 1 1 d . . . . .
H10 H 0.6887 0.9987 0.3856 0.044 Uiso 1 1 calc R . . . .
C11 C 0.6994(3) 0.8847(3) 0.28081(18) 0.0335(6) Uani 1 1 d . . . . .
C12 C 0.5496(3) 0.7857(3) 0.26113(18) 0.0336(6) Uani 1 1 d . . . . .
H12 H 0.5044 0.8382 0.2547 0.040 Uiso 1 1 calc R . . . .
C13 C 0.4784(3) 0.6827(3) 0.33615(19) 0.0350(6) Uani 1 1 d . . . . .
C14 C 0.5109(4) 0.5709(3) 0.3342(2) 0.0440(7) Uani 1 1 d . . . . .
H14 H 0.5072 0.5280 0.3875 0.053 Uiso 1 1 calc R . . . .
C15 C 0.5444(4) 0.5310(4) 0.2611(3) 0.0502(8) Uani 1 1 d . . . . .
H15 H 0.5565 0.4572 0.2641 0.060 Uiso 1 1 calc R . . . .
C16 C 0.5630(4) 0.5993(4) 0.1753(2) 0.0469(8) Uani 1 1 d . . . . .
C17 C 0.5361(3) 0.7139(3) 0.17206(19) 0.0400(7) Uani 1 1 d . . . . .
H17A H 0.4460 0.6805 0.1496 0.048 Uiso 1 1 calc R . . . .
H17B H 0.5973 0.7792 0.1295 0.048 Uiso 1 1 calc R . . . .
C18 C 0.7579(3) 1.0026(3) 0.21396(19) 0.0378(6) Uani 1 1 d . . . . .
C19 C 0.7001(3) 1.0922(3) 0.1983(2) 0.0359(6) Uani 1 1 d . . . . .
C20 C 0.7472(4) 1.1749(4) 0.1233(2) 0.0464(7) Uani 1 1 d . . . . .
H20 H 0.8128 1.1741 0.0877 0.056 Uiso 1 1 calc R . . . .
C21 C 0.6970(5) 1.2573(4) 0.1020(3) 0.0622(11) Uani 1 1 d . . . . .
H21 H 0.7281 1.3109 0.0514 0.075 Uiso 1 1 calc R . . . .
C22 C 0.6013(5) 1.2616(4) 0.1545(3) 0.0601(10) Uani 1 1 d . . . . .
H22 H 0.5680 1.3176 0.1395 0.072 Uiso 1 1 calc R . . . .
C23 C 0.5552(4) 1.1822(4) 0.2298(3) 0.0497(8) Uani 1 1 d . . . . .
H23 H 0.4915 1.1855 0.2659 0.060 Uiso 1 1 calc R . . . .
C24 C 0.6039(3) 1.0973(3) 0.2515(2) 0.0396(6) Uani 1 1 d . . . . .
H24 H 0.5720 1.0435 0.3019 0.048 Uiso 1 1 calc R . . . .
C25 C 0.3256(3) 0.6221(3) 0.3272(2) 0.0382(6) Uani 1 1 d . . . . .
H25A H 0.3047 0.6935 0.3330 0.046 Uiso 1 1 calc R . . . .
H25B H 0.2987 0.5845 0.2679 0.046 Uiso 1 1 calc R . . . .
C26 C 0.2431(4) 0.5134(3) 0.3956(3) 0.0482(8) Uani 1 1 d . . . . .
H26A H 0.2542 0.4367 0.3847 0.058 Uiso 1 1 calc R . . . .
H26B H 0.2776 0.5471 0.4548 0.058 Uiso 1 1 calc R . . . .
C27 C 0.0951(4) 0.4683(4) 0.3934(3) 0.0529(9) Uani 1 1 d . . . . .
H27A H 0.0519 0.4090 0.4436 0.064 Uiso 1 1 calc R . . . .
H27B H 0.0847 0.5461 0.4012 0.064 Uiso 1 1 calc R . . . .
C28 C 0.0242(4) 0.3973(5) 0.3092(3) 0.0684(11) Uani 1 1 d . . . . .
H28A H 0.0644 0.4559 0.2592 0.103 Uiso 1 1 calc GR . . . .
H28B H -0.0685 0.3721 0.3131 0.103 Uiso 1 1 calc GR . . . .
H28C H 0.0315 0.3185 0.3016 0.103 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.209(5) . ?
O2 H2 0.8200 . ?
O2 C11 1.422(4) . ?
O3 C9 1.430(4) . ?
O3 C13 1.433(3) . ?
O4 C16 1.217(5) . ?
O5 C18 1.205(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(6) . ?
C1 C6 1.384(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(5) . ?
C6 C7 1.511(5) . ?
C7 C8 1.503(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C10 1.532(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.514(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.552(4) . ?
C11 C12 1.550(4) . ?
C11 C18 1.547(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.541(4) . ?
C12 C17 1.539(4) . ?
C13 C14 1.512(4) . ?
C13 C25 1.543(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.319(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.467(6) . ?
C16 C17 1.501(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.503(4) . ?
C19 C20 1.396(4) . ?
C19 C24 1.391(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.388(5) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.529(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.515(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.506(7) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 H2 109.5 . . ?
C9 O3 C13 113.9(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.1(4) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(5) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 C7 122.1(3) . . ?
C5 C6 C7 118.7(4) . . ?
O1 C7 C6 120.5(3) . . ?
O1 C7 C8 122.9(3) . . ?
C8 C7 C6 116.6(3) . . ?
C7 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C7 C8 C10 116.1(3) . . ?
H8A C8 H8B 107.4 . . ?
C10 C8 H8A 108.3 . . ?
C10 C8 H8B 108.3 . . ?
O3 C9 H9A 109.4 . . ?
O3 C9 H9B 109.4 . . ?
O3 C9 C10 111.3(2) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C10 H10 109.3 . . ?
C8 C10 C11 109.0(2) . . ?
C9 C10 C8 111.8(2) . . ?
C9 C10 H10 109.3 . . ?
C9 C10 C11 108.0(2) . . ?
C11 C10 H10 109.3 . . ?
O2 C11 C10 107.8(2) . . ?
O2 C11 C12 107.4(2) . . ?
O2 C11 C18 107.0(2) . . ?
C12 C11 C10 112.9(2) . . ?
C18 C11 C10 110.3(2) . . ?
C18 C11 C12 111.1(2) . . ?
C11 C12 H12 107.8 . . ?
C13 C12 C11 113.4(2) . . ?
C13 C12 H12 107.8 . . ?
C17 C12 C11 109.7(2) . . ?
C17 C12 H12 107.8 . . ?
C17 C12 C13 110.3(2) . . ?
O3 C13 C12 110.6(2) . . ?
O3 C13 C14 110.1(2) . . ?
O3 C13 C25 105.0(2) . . ?
C12 C13 C25 109.5(2) . . ?
C14 C13 C12 112.3(2) . . ?
C14 C13 C25 109.1(3) . . ?
C13 C14 H14 118.2 . . ?
C15 C14 C13 123.6(3) . . ?
C15 C14 H14 118.2 . . ?
C14 C15 H15 118.9 . . ?
C14 C15 C16 122.1(3) . . ?
C16 C15 H15 118.9 . . ?
O4 C16 C15 121.6(4) . . ?
O4 C16 C17 120.8(4) . . ?
C15 C16 C17 117.5(3) . . ?
C12 C17 H17A 108.3 . . ?
C12 C17 H17B 108.3 . . ?
C16 C17 C12 115.9(3) . . ?
C16 C17 H17A 108.3 . . ?
C16 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
O5 C18 C11 117.5(3) . . ?
O5 C18 C19 118.7(3) . . ?
C19 C18 C11 123.9(2) . . ?
C20 C19 C18 116.1(3) . . ?
C24 C19 C18 125.2(3) . . ?
C24 C19 C20 118.6(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.9(4) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.1(4) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C13 C25 H25A 108.6 . . ?
C13 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 C13 114.5(3) . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C27 C26 C25 113.5(3) . . ?
C27 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C26 C27 H27A 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C28 C27 C26 114.7(3) . . ?
C28 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O5 0.82 2.02 2.539(4) 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 C7 C8 C10 -1.4(5) . . . . ?
O2 C11 C12 C13 75.1(3) . . . . ?
O2 C11 C12 C17 -48.7(3) . . . . ?
O2 C11 C18 O5 -6.7(4) . . . . ?
O2 C11 C18 C19 172.5(3) . . . . ?
O3 C9 C10 C8 -178.8(2) . . . . ?
O3 C9 C10 C11 -58.8(3) . . . . ?
O3 C13 C14 C15 -151.2(3) . . . . ?
O3 C13 C25 C26 -63.9(3) . . . . ?
O4 C16 C17 C12 -158.9(3) . . . . ?
O5 C18 C19 C20 12.2(5) . . . . ?
O5 C18 C19 C24 -168.7(4) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C1 C6 C7 O1 178.2(4) . . . . ?
C1 C6 C7 C8 -1.5(5) . . . . ?
C2 C1 C6 C5 1.7(5) . . . . ?
C2 C1 C6 C7 -177.7(3) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C4 C5 C6 C7 178.1(4) . . . . ?
C5 C6 C7 O1 -1.2(5) . . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C6 C7 C8 C10 178.3(3) . . . . ?
C7 C8 C10 C9 -68.8(4) . . . . ?
C7 C8 C10 C11 171.8(3) . . . . ?
C8 C10 C11 O2 51.8(3) . . . . ?
C8 C10 C11 C12 170.3(2) . . . . ?
C8 C10 C11 C18 -64.8(3) . . . . ?
C9 O3 C13 C12 -57.3(3) . . . . ?
C9 O3 C13 C14 67.5(3) . . . . ?
C9 O3 C13 C25 -175.3(2) . . . . ?
C9 C10 C11 O2 -69.9(3) . . . . ?
C9 C10 C11 C12 48.6(3) . . . . ?
C9 C10 C11 C18 173.6(2) . . . . ?
C10 C11 C12 C13 -43.7(3) . . . . ?
C10 C11 C12 C17 -167.4(2) . . . . ?
C10 C11 C18 O5 110.4(4) . . . . ?
C10 C11 C18 C19 -70.4(4) . . . . ?
C11 C12 C13 O3 45.7(3) . . . . ?
C11 C12 C13 C14 -77.8(3) . . . . ?
C11 C12 C13 C25 160.9(2) . . . . ?
C11 C12 C17 C16 79.8(3) . . . . ?
C11 C18 C19 C20 -167.0(3) . . . . ?
C11 C18 C19 C24 12.1(5) . . . . ?
C12 C11 C18 O5 -123.7(4) . . . . ?
C12 C11 C18 C19 55.5(4) . . . . ?
C12 C13 C14 C15 -27.4(5) . . . . ?
C12 C13 C25 C26 177.4(3) . . . . ?
C13 O3 C9 C10 66.1(3) . . . . ?
C13 C12 C17 C16 -45.8(4) . . . . ?
C13 C14 C15 C16 4.8(6) . . . . ?
C13 C25 C26 C27 172.5(3) . . . . ?
C14 C13 C25 C26 54.2(4) . . . . ?
C14 C15 C16 O4 -179.3(4) . . . . ?
C14 C15 C16 C17 -2.9(6) . . . . ?
C15 C16 C17 C12 24.6(5) . . . . ?
C17 C12 C13 O3 169.2(2) . . . . ?
C17 C12 C13 C14 45.7(3) . . . . ?
C17 C12 C13 C25 -75.6(3) . . . . ?
C18 C11 C12 C13 -168.2(2) . . . . ?
C18 C11 C12 C17 68.0(3) . . . . ?
C18 C19 C20 C21 177.9(3) . . . . ?
C18 C19 C24 C23 -178.6(3) . . . . ?
C19 C20 C21 C22 1.0(6) . . . . ?
C20 C19 C24 C23 0.5(5) . . . . ?
C20 C21 C22 C23 0.1(7) . . . . ?
C21 C22 C23 C24 -0.8(6) . . . . ?
C22 C23 C24 C19 0.5(6) . . . . ?
C24 C19 C20 C21 -1.3(5) . . . . ?
C25 C13 C14 C15 94.1(4) . . . . ?
C25 C26 C27 C28 66.1(4) . . . . ?

_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 1.126
_oxdiff_exptl_absorpt_empirical_full_min 0.910
