# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

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

data_a5_ads58_catraneiolidea
_database_code_depnum_ccdc_archive 'CCDC 2366244'
loop_
_audit_author_name
_audit_author_address
'Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2025-06-19 downloaded from the CCDC.
;
_audit_creation_date             2024-06-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 O8'
_chemical_formula_sum            'C22 H28 O8'
_chemical_formula_weight         420.44
_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 0.0181 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                   8.25833(10)
_cell_length_b                   12.69524(15)
_cell_length_c                   20.3354(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2131.99(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9666
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.69
_cell_measurement_theta_min      5.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1649 before and 0.0780 after correction.
The Ratio of minimum to maximum transmission is 0.3606.
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    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5.00 0.00 4.00 0.1460
-4.00 -2.00 5.00 0.1290
-4.00 3.00 -4.00 0.1330
-1.00 -3.00 -5.00 0.0860
0.00 2.00 -3.00 0.0930
0.00 -3.00 5.00 0.0880
0.00 -4.00 3.00 0.0900
1.00 3.00 5.00 0.1110
5.00 1.00 -5.00 0.0700

_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.187
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22105
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.685
_diffrn_reflns_theta_min         5.574
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Bruker PHOTON III C7'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CPAD
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker D8 Venture dual source kappa CPAD'
_diffrn_measurement_device_type  'Bristol D8 Venture Cu Source'
_diffrn_measurement_method       'φ and ω-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\uS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3719
_reflns_number_total             3875
_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 v8.39.0 (Bruker, 2018)'
_computing_data_collection       'Bruker SC-XRD Suite'
_computing_data_reduction        'SAINT v8.39.0 (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
unknown
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.117
_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)+(0.1724P)²+0.3296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2102
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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. Restrained distances
 C15A-C14 \\sim C15-C14 \\sim C16A-C15A \\sim C16-C15 \\sim C17A-C16A \\sim
C17-C16 \\sim C18-C17 ~
 C18A-C17A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C15A)
4. Others
 Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=
 Sof(H16D)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18A)=Sof(H18B)=
 Sof(H18C)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18D)=Sof(H18E)=Sof(H18F)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5A)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C14(H14A,H14B), C14(H14C,H14D), C15(H15A,H15B),
 C15A(H15C,H15D), C16(H16A,H16B), C16A(H16C,H16D), C17(H17A,H17B), C17A(H17C,
 H17D), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
5.c Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18(H18D,H18E,H18F), C22(H22A,H22B,H22C)
5.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1438(4) 0.7359(3) 0.28824(15) 0.0421(8) Uani 1 1 d . . . . .
C1 C 0.6402(5) 0.7431(3) 0.21843(16) 0.0224(7) Uani 1 1 d . . . . .
H1 H 0.701826 0.798613 0.194088 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7476(4) 0.6441(3) 0.22058(16) 0.0228(7) Uani 1 1 d . . . . .
H2A H 0.683897 0.584547 0.238360 0.027 Uiso 1 1 calc R U . . .
H2B H 0.781078 0.625654 0.175280 0.027 Uiso 1 1 calc R U . . .
O2 O 1.0324(5) 0.7860(3) 0.19229(17) 0.0485(9) Uani 1 1 d . . . . .
C3 C 0.8942(4) 0.6595(3) 0.26172(16) 0.0236(7) Uani 1 1 d . . . . .
O3 O 1.1768(4) 0.6571(3) 0.38672(17) 0.0504(9) Uani 1 1 d . . . . .
C4 C 0.9361(4) 0.6225(3) 0.32134(18) 0.0238(7) Uani 1 1 d . . . . .
O4 O 0.7712(4) 0.4655(2) 0.33222(14) 0.0321(6) Uani 1 1 d . . . . .
H4 H 0.836754 0.416084 0.325347 0.048 Uiso 1 1 calc R U . . .
O5 O 0.7985(3) 0.70092(19) 0.43255(12) 0.0244(6) Uani 1 1 d . . . . .
H5 H 0.864740 0.687603 0.462768 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8508(4) 0.5477(3) 0.36668(17) 0.0246(8) Uani 1 1 d . . . . .
H5A H 0.933796 0.515055 0.396099 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7252(4) 0.6055(3) 0.41074(15) 0.0203(7) Uani 1 1 d . . . . .
O6 O 0.5237(4) 0.9269(2) 0.35328(14) 0.0364(7) Uani 1 1 d . . . . .
C7 C 0.5716(4) 0.6356(3) 0.37057(16) 0.0206(7) Uani 1 1 d . . . . .
H7A H 0.560987 0.586049 0.333249 0.025 Uiso 1 1 calc R U . . .
H7B H 0.475392 0.626417 0.399026 0.025 Uiso 1 1 calc R U . . .
O7 O 0.4738(4) 0.8313(3) 0.44372(13) 0.0412(8) Uani 1 1 d . . . . .
C8 C 0.5714(4) 0.7451(3) 0.34433(16) 0.0206(7) Uani 1 1 d . . . . .
O8 O 0.5987(5) 0.9701(2) 0.25032(14) 0.0434(8) Uani 1 1 d . . . . .
C9 C 0.5995(4) 0.7873(3) 0.28475(16) 0.0201(7) Uani 1 1 d . . . . .
C10 C 1.0247(5) 0.7335(3) 0.2412(2) 0.0330(9) Uani 1 1 d . . . . .
C11 C 1.0949(4) 0.6687(4) 0.3393(2) 0.0329(9) Uani 1 1 d . . . . .
C12 C 0.5183(5) 0.8326(3) 0.38804(18) 0.0279(8) Uani 1 1 d . . . . .
C13 C 0.5761(6) 0.9032(3) 0.29005(17) 0.0310(9) Uani 1 1 d . . . . .
C14 C 0.4820(5) 0.7240(3) 0.18056(17) 0.0272(8) Uani 1 1 d D . . . .
H14A H 0.417544 0.672432 0.206027 0.033 Uiso 0.556(14) 1 calc R U P A 1
H14B H 0.420519 0.790976 0.180651 0.033 Uiso 0.556(14) 1 calc R U P A 1
H14C H 0.427265 0.660385 0.197839 0.033 Uiso 0.444(14) 1 calc R U P A 2
H14D H 0.408318 0.784830 0.186407 0.033 Uiso 0.444(14) 1 calc R U P A 2
C15 C 0.4887(16) 0.6852(13) 0.1100(4) 0.031(3) Uani 0.556(14) 1 d D . P A 1
H15A H 0.554159 0.734865 0.083526 0.037 Uiso 0.556(14) 1 calc R U P A 1
H15B H 0.543103 0.615739 0.108899 0.037 Uiso 0.556(14) 1 calc R U P A 1
C15A C 0.520(2) 0.7094(18) 0.1082(5) 0.031(3) Uani 0.444(14) 1 d D . P A 2
H15C H 0.564536 0.776312 0.090973 0.037 Uiso 0.444(14) 1 calc R U P A 2
H15D H 0.605499 0.655208 0.104049 0.037 Uiso 0.444(14) 1 calc R U P A 2
C16 C 0.3227(16) 0.6752(12) 0.0798(5) 0.038(3) Uani 0.556(14) 1 d D . P A 1
H16A H 0.275128 0.746372 0.074907 0.046 Uiso 0.556(14) 1 calc R U P A 1
H16B H 0.252307 0.634597 0.109994 0.046 Uiso 0.556(14) 1 calc R U P A 1
C16A C 0.379(2) 0.6776(18) 0.0660(6) 0.043(4) Uani 0.444(14) 1 d D . P A 2
H16C H 0.292547 0.730416 0.072566 0.052 Uiso 0.444(14) 1 calc R U P A 2
H16D H 0.337785 0.609756 0.083162 0.052 Uiso 0.444(14) 1 calc R U P A 2
C17 C 0.3245(13) 0.6216(7) 0.0135(4) 0.042(3) Uani 0.556(14) 1 d D . P A 1
H17A H 0.373262 0.550830 0.018421 0.050 Uiso 0.556(14) 1 calc R U P A 1
H17B H 0.211531 0.612133 -0.001632 0.050 Uiso 0.556(14) 1 calc R U P A 1
C17A C 0.4031(18) 0.6650(14) -0.0068(6) 0.059(4) Uani 0.444(14) 1 d D . P A 2
H17C H 0.401234 0.735872 -0.027013 0.070 Uiso 0.444(14) 1 calc R U P A 2
H17D H 0.512351 0.635198 -0.014203 0.070 Uiso 0.444(14) 1 calc R U P A 2
C18A C 0.2832(16) 0.5974(11) -0.0422(6) 0.058(4) Uani 0.444(14) 1 d D . P A 2
H18A H 0.307027 0.598129 -0.089399 0.087 Uiso 0.444(14) 1 calc R U P A 2
H18B H 0.173705 0.624727 -0.034755 0.087 Uiso 0.444(14) 1 calc R U P A 2
H18C H 0.290159 0.525032 -0.025651 0.087 Uiso 0.444(14) 1 calc R U P A 2
C18 C 0.4163(16) 0.6810(9) -0.0378(5) 0.052(3) Uani 0.556(14) 1 d D . P A 1
H18D H 0.396435 0.649279 -0.080971 0.078 Uiso 0.556(14) 1 calc R U P A 1
H18E H 0.532312 0.678178 -0.027841 0.078 Uiso 0.556(14) 1 calc R U P A 1
H18F H 0.380309 0.754583 -0.038209 0.078 Uiso 0.556(14) 1 calc R U P A 1
C19 C 0.6823(5) 0.5334(3) 0.46837(17) 0.0256(7) Uani 1 1 d . . . . .
H19A H 0.630747 0.469078 0.450549 0.031 Uiso 1 1 calc R U . . .
H19B H 0.784097 0.511685 0.490178 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5703(5) 0.5800(3) 0.52029(18) 0.0310(9) Uani 1 1 d . . . . .
H20A H 0.606034 0.652539 0.530754 0.037 Uiso 1 1 calc R U . . .
H20B H 0.458995 0.584001 0.502432 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5692(7) 0.5151(4) 0.5825(2) 0.0433(11) Uani 1 1 d . . . . .
H21A H 0.678601 0.517248 0.602341 0.052 Uiso 1 1 calc R U . . .
H21B H 0.545574 0.440940 0.570903 0.052 Uiso 1 1 calc R U . . .
C22 C 0.4473(8) 0.5515(4) 0.6331(2) 0.0491(13) Uani 1 1 d . . . . .
H22A H 0.339152 0.553132 0.613341 0.074 Uiso 1 1 calc R U . . .
H22B H 0.476297 0.622205 0.648437 0.074 Uiso 1 1 calc R U . . .
H22C H 0.447514 0.502643 0.670465 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.372(6) . ?
O1 C11 1.403(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.539(5) . ?
C1 C9 1.499(4) . ?
C1 C14 1.536(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.484(5) . ?
O2 C10 1.198(5) . ?
C3 C4 1.346(5) . ?
C3 C10 1.489(5) . ?
O3 C11 1.186(5) . ?
C4 C5 1.499(5) . ?
C4 C11 1.483(5) . ?
O4 H4 0.8400 . ?
O4 C5 1.418(4) . ?
O5 H5 0.8400 . ?
O5 C6 1.424(4) . ?
C5 H5A 1.0000 . ?
C5 C6 1.555(5) . ?
C6 C7 1.556(5) . ?
C6 C19 1.529(4) . ?
O6 C12 1.391(5) . ?
O6 C13 1.390(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.489(5) . ?
O7 C12 1.190(5) . ?
C8 C9 1.345(5) . ?
C8 C12 1.489(5) . ?
O8 C13 1.187(5) . ?
C9 C13 1.487(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 C15 1.517(8) . ?
C14 C15A 1.515(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.508(10) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.501(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.510(10) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C17A 1.501(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.493(9) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C18A 1.495(10) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.523(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.509(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.512(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C11 107.3(3) . . ?
C2 C1 H1 107.2 . . ?
C9 C1 H1 107.2 . . ?
C9 C1 C2 114.2(3) . . ?
C9 C1 C14 108.6(3) . . ?
C14 C1 H1 107.2 . . ?
C14 C1 C2 112.1(3) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 112.2(3) . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C2 C3 C10 121.0(3) . . ?
C4 C3 C2 132.2(3) . . ?
C4 C3 C10 106.7(4) . . ?
C3 C4 C5 130.9(3) . . ?
C3 C4 C11 108.1(3) . . ?
C11 C4 C5 121.0(3) . . ?
C5 O4 H4 109.5 . . ?
C6 O5 H5 109.5 . . ?
C4 C5 H5A 107.9 . . ?
C4 C5 C6 111.6(3) . . ?
O4 C5 C4 112.3(3) . . ?
O4 C5 H5A 108.0 . . ?
O4 C5 C6 108.9(3) . . ?
C6 C5 H5A 107.9 . . ?
O5 C6 C5 107.3(3) . . ?
O5 C6 C7 107.5(3) . . ?
O5 C6 C19 111.6(3) . . ?
C5 C6 C7 110.9(3) . . ?
C19 C6 C5 108.3(3) . . ?
C19 C6 C7 111.1(3) . . ?
C13 O6 C12 107.1(3) . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.7(3) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C9 C8 C7 134.0(3) . . ?
C9 C8 C12 106.9(3) . . ?
C12 C8 C7 118.9(3) . . ?
C8 C9 C1 134.4(3) . . ?
C8 C9 C13 107.8(3) . . ?
C13 C9 C1 117.7(3) . . ?
O1 C10 C3 109.7(3) . . ?
O2 C10 O1 121.9(4) . . ?
O2 C10 C3 128.4(4) . . ?
O1 C11 C4 108.2(3) . . ?
O3 C11 O1 120.9(4) . . ?
O3 C11 C4 130.9(4) . . ?
O6 C12 C8 109.2(3) . . ?
O7 C12 O6 120.4(4) . . ?
O7 C12 C8 130.4(4) . . ?
O6 C13 C9 108.8(3) . . ?
O8 C13 O6 121.6(3) . . ?
O8 C13 C9 129.7(4) . . ?
C1 C14 H14A 107.4 . . ?
C1 C14 H14B 107.4 . . ?
C1 C14 H14C 109.8 . . ?
C1 C14 H14D 109.8 . . ?
H14A C14 H14B 107.0 . . ?
H14C C14 H14D 108.3 . . ?
C15 C14 C1 119.6(6) . . ?
C15 C14 H14A 107.4 . . ?
C15 C14 H14B 107.4 . . ?
C15A C14 C1 109.3(7) . . ?
C15A C14 H14C 109.8 . . ?
C15A C14 H14D 109.8 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.3(9) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15A H15C 108.4 . . ?
C14 C15A H15D 108.4 . . ?
H15C C15A H15D 107.5 . . ?
C16A C15A C14 115.4(11) . . ?
C16A C15A H15C 108.4 . . ?
C16A C15A H15D 108.4 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C15 C16 C17 113.1(10) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15A C16A H16C 107.5 . . ?
C15A C16A H16D 107.5 . . ?
C15A C16A C17A 119.4(12) . . ?
H16C C16A H16D 107.0 . . ?
C17A C16A H16C 107.5 . . ?
C17A C16A H16D 107.5 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.7(8) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16A C17A H17C 108.1 . . ?
C16A C17A H17D 108.1 . . ?
H17C C17A H17D 107.3 . . ?
C18A C17A C16A 116.7(13) . . ?
C18A C17A H17C 108.1 . . ?
C18A C17A H17D 108.1 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
C17 C18 H18E 109.5 . . ?
C17 C18 H18F 109.5 . . ?
H18D C18 H18E 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C6 C19 H19A 108.3 . . ?
C6 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C20 C19 C6 116.1(3) . . ?
C20 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 111.9(3) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C20 C21 C22 114.1(4) . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O2 0.84 2.01 2.841(4) 172.5 4_745 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
C1 C2 C3 C4 107.4(4) . . . . ?
C1 C2 C3 C10 -67.8(4) . . . . ?
C1 C9 C13 O6 174.1(3) . . . . ?
C1 C9 C13 O8 -7.5(7) . . . . ?
C1 C14 C15 C16 -177.6(9) . . . . ?
C1 C14 C15A C16A 173.2(15) . . . . ?
C2 C1 C9 C8 -34.3(6) . . . . ?
C2 C1 C9 C13 148.7(3) . . . . ?
C2 C1 C14 C15 -56.5(8) . . . . ?
C2 C1 C14 C15A -68.9(10) . . . . ?
C2 C3 C4 C5 3.0(6) . . . . ?
C2 C3 C4 C11 -177.3(4) . . . . ?
C2 C3 C10 O1 178.2(3) . . . . ?
C2 C3 C10 O2 -1.2(6) . . . . ?
C3 C4 C5 O4 37.4(5) . . . . ?
C3 C4 C5 C6 -85.2(5) . . . . ?
C3 C4 C11 O1 0.9(4) . . . . ?
C3 C4 C11 O3 -179.2(5) . . . . ?
C4 C3 C10 O1 1.9(4) . . . . ?
C4 C3 C10 O2 -177.4(4) . . . . ?
C4 C5 C6 O5 -42.3(4) . . . . ?
C4 C5 C6 C7 74.9(4) . . . . ?
C4 C5 C6 C19 -163.0(3) . . . . ?
O4 C5 C6 O5 -166.9(3) . . . . ?
O4 C5 C6 C7 -49.7(4) . . . . ?
O4 C5 C6 C19 72.5(3) . . . . ?
O5 C6 C7 C8 21.2(4) . . . . ?
O5 C6 C19 C20 57.3(4) . . . . ?
C5 C4 C11 O1 -179.4(3) . . . . ?
C5 C4 C11 O3 0.5(7) . . . . ?
C5 C6 C7 C8 -95.8(3) . . . . ?
C5 C6 C19 C20 175.3(3) . . . . ?
C6 C7 C8 C9 102.3(5) . . . . ?
C6 C7 C8 C12 -83.3(4) . . . . ?
C6 C19 C20 C21 -165.4(4) . . . . ?
C7 C6 C19 C20 -62.7(4) . . . . ?
C7 C8 C9 C1 1.4(7) . . . . ?
C7 C8 C9 C13 178.6(4) . . . . ?
C7 C8 C12 O6 -178.6(3) . . . . ?
C7 C8 C12 O7 0.4(7) . . . . ?
C8 C9 C13 O6 -3.7(5) . . . . ?
C8 C9 C13 O8 174.7(5) . . . . ?
C9 C1 C2 C3 -51.2(4) . . . . ?
C9 C1 C14 C15 176.4(8) . . . . ?
C9 C1 C14 C15A 164.1(10) . . . . ?
C9 C8 C12 O6 -2.8(4) . . . . ?
C9 C8 C12 O7 176.2(4) . . . . ?
C10 O1 C11 O3 -179.6(4) . . . . ?
C10 O1 C11 C4 0.3(4) . . . . ?
C10 C3 C4 C5 178.6(4) . . . . ?
C10 C3 C4 C11 -1.6(4) . . . . ?
C11 O1 C10 O2 178.1(4) . . . . ?
C11 O1 C10 C3 -1.3(4) . . . . ?
C11 C4 C5 O4 -142.3(3) . . . . ?
C11 C4 C5 C6 95.1(4) . . . . ?
C12 O6 C13 O8 -176.7(4) . . . . ?
C12 O6 C13 C9 1.8(5) . . . . ?
C12 C8 C9 C1 -173.4(4) . . . . ?
C12 C8 C9 C13 3.8(4) . . . . ?
C13 O6 C12 O7 -178.6(4) . . . . ?
C13 O6 C12 C8 0.4(5) . . . . ?
C14 C1 C2 C3 -175.3(3) . . . . ?
C14 C1 C9 C8 91.5(5) . . . . ?
C14 C1 C9 C13 -85.5(4) . . . . ?
C14 C15 C16 C17 -171.4(11) . . . . ?
C14 C15A C16A C17A 177.8(17) . . . . ?
C15 C16 C17 C18 -63.4(14) . . . . ?
C15A C16A C17A C18A 158.2(18) . . . . ?
C19 C6 C7 C8 143.7(3) . . . . ?
C19 C20 C21 C22 -174.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
