#------------------------------------------------------------------------------
#$Date: 2025-07-05 04:27:18 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300357 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/06/7250661.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7250661
loop_
_publ_author_name
'Williams, Katherine'
'Spencer, Catherine E.'
'de Mattos-Shipley, Kate M. J.'
'Shah, Anjali D.'
'Dao, Trong-Tuan'
'Davies, Jonathan A.'
'Heard, David M.'
'Song, Zhongshu'
'Winter, Ashley J.'
'Crump, Matthew P.'
'Willis, Christine L.'
'Bailey, Andrew M.'
_publ_section_title
;
 In vivo and in vitro investigations provide insights into maleidride
 biosynthesis in fungi
;
_journal_issue                   28
_journal_name_full               'RSC Advances'
_journal_page_first              22799
_journal_page_last               22806
_journal_paper_doi               10.1039/D5RA02147B
_journal_volume                  15
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H28 O8'
_chemical_formula_sum            'C22 H28 O8'
_chemical_formula_weight         420.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-27 deposited with the CCDC.	2025-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.25833(10)
_cell_length_b                   12.69524(15)
_cell_length_c                   20.3354(3)
_cell_measurement_reflns_used    9666
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.69
_cell_measurement_theta_min      5.36
_cell_volume                     2131.99(5)
_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)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Bruker PHOTON III C7'
_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_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_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
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.187
_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_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_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0642
_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
_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_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ra02147b2.cif
_cod_data_source_block           a5_ads58_catraneiolidea
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        2131.99(4)
_cod_database_code               7250661
_shelx_shelxl_version_number     2017/1
_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.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 . . .
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'
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
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_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_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) . . . . ?
