#------------------------------------------------------------------------------
#$Date: 2021-11-04 02:34:57 +0200 (Thu, 04 Nov 2021) $
#$Revision: 270282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565111.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_1565111
loop_
_publ_author_name
'Huang, Zhong-Hui'
'Liang, Xiao'
'Li, Chan-Juan'
'Gu, Qiong'
'Ma, Xuan'
'Qi, Shu-Hua'
_publ_section_title
;
 Talaromynoids A-I, Highly Oxygenated Meroterpenoids from the
 Marine-Derived Fungus Talaromyces purpureogenus SCSIO 41517 and
 Their Lipid Accumulation Inhibitory Activities.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2727
_journal_page_last               2737
_journal_paper_doi               10.1021/acs.jnatprod.1c00681
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H32 O10'
_chemical_formula_sum            'C26 H32 O10'
_chemical_formula_weight         504.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                112.706(3)
_cell_angle_beta                 95.017(2)
_cell_angle_gamma                110.165(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2185(2)
_cell_length_b                   8.4465(2)
_cell_length_c                   10.2022(3)
_cell_measurement_reflns_used    9675
_cell_measurement_temperature    106(9)
_cell_measurement_theta_max      74.1200
_cell_measurement_theta_min      4.8510
_cell_volume                     593.06(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(9)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -13.00  16.00   0.50    0.58    --    0.00 -38.00 120.00   58
  2  ω    -29.00  31.00   0.50    0.58    --    0.00 -82.00   0.00  120
  3  ω     27.00  71.00   0.50    0.58    --    0.00  38.00  60.00   88
  4  ω    -89.00 -41.00   0.50    0.58    --    0.00 -38.00 120.00   96
  5  ω    -37.00  15.00   0.50    0.58    --    0.00 -38.00-180.00  104
  6  ω    -13.00  22.00   0.50    0.58    --    0.00  38.00  60.00   70
  7  ω    -89.00 -56.00   0.50    0.58    --    0.00 -38.00-180.00   66
  8  ω    -10.00  16.00   0.50    0.58    --    0.00 -38.00 -60.00   52
  9  ω     -9.00  21.00   0.50    0.58    --    0.00 -77.00 -60.00   60
 10  ω    -43.00 -17.00   0.50    0.58    --    0.00 -77.00 -60.00   52
 11  ω    -87.00 -47.00   0.50    0.58    --    0.00 -38.00 -60.00   80
 12  ω    -44.00 -11.00   0.50    0.58    --    0.00 -77.00-120.00   66
 13  ω     72.00 111.00   0.50    1.50    --   95.80  61.00-180.00   78
 14  ω     71.00 105.00   0.50    1.50    --   95.80  66.00-109.78   68
 15  ω     18.00 109.00   0.50    1.50    --   95.80 -82.00   0.00  182
 16  ω     95.00 121.00   0.50    1.50    --   95.80 -77.00-180.00   52
 17  ω     68.00 109.00   0.50    1.50    --   95.80  75.00  -9.46   82
 18  ω     73.00 110.00   0.50    1.50    --   95.80  58.00 -35.72   74
 19  ω     72.00  98.00   0.50    1.50    --   95.80  61.00 -60.00   52
 20  ω      6.00  81.00   0.50    1.50    --   95.80 -77.00-180.00  150
 21  ω    150.00 176.00   0.50    1.50    --   95.80  61.00  30.00   52
 22  ω    107.00 133.00   0.50    1.50    --   95.80  61.00 -60.00   52
 23  ω     72.00 101.00   0.50    1.50    --   95.80  62.00  79.09   58
 24  ω      7.00  82.00   0.50    1.50    --   95.80 -77.00  30.00  150
 25  ω     49.00 119.00   0.50    1.50    --   95.80 -82.00 -90.00  140
 26  ω     82.00 108.00   0.50    1.50    --   95.80  45.00 150.00   52
 27  ω     72.00 128.00   0.50    1.50    --   95.80  61.00  30.00  112
 28  ω    129.00 185.00   0.50    1.50    --   95.80  70.00-102.80  112
 29  ω     77.00 107.00   0.50    1.50    --   95.80  44.00-140.32   60
 30  ω     77.00 179.00   0.50    1.50    --   95.80  45.00   0.00  204
 31  ω     72.00  97.00   0.50    1.50    --   95.80  61.00-120.00   50
 32  ω     56.00 127.00   0.50    1.50    --   95.80 -82.00 120.00  142
 33  ω    132.00 185.00   0.50    1.50    --   95.80  61.00  90.00  106
 34  ω     69.00  99.00   0.50    1.50    --   95.80  70.00-102.80   60
 35  ω      8.00  41.00   0.50    1.50    --   95.80 -82.00 120.00   66
 36  ω     79.00 118.00   0.50    1.50    --   95.80  45.00 -60.00   78
 37  ω     72.00 104.00   0.50    1.50    --   95.80  61.00 150.00   64
 38  ω     72.00 125.00   0.50    1.50    --   95.80  61.00  90.00  106
 39  ω    110.00 185.00   0.50    1.50    --   95.80  61.00-150.00  150
 40  ω     76.00 148.00   0.50    1.50    --   95.80  45.00-120.00  144
 41  ω      9.00 117.00   0.50    1.50    --   95.80 -61.00-150.00  216
 42  ω     72.00  97.00   0.50    1.50    --   95.80  61.00-150.00   50
 43  ω     74.00 181.00   0.50    1.50    --   95.80  53.00  60.06  214
 44  ω     72.00  98.00   0.50    1.50    --   95.80  61.00 -30.00   52
 45  ω     72.00  98.00   0.50    1.50    --   95.80  61.00   0.00   52
 46  ω     75.00 100.00   0.50    1.50    --   95.80  61.00 120.00   50
 47  ω    116.00 157.00   0.50    1.50    --   95.80  58.00 -35.72   82
 48  ω     77.00 103.00   0.50    1.50    --   95.80  61.00  60.00   52
 49  ω    152.00 184.00   0.50    1.50    --   95.80  38.00 140.72   64
 50  ω     88.00 122.00   0.50    1.50    --   95.80 -77.00  30.00   68
 51  ω     81.00 125.00   0.50    1.50    --   95.80  30.00-180.00   88
 52  ω     78.00 109.00   0.50    1.50    --   95.80  38.00 140.72   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1977863000
_diffrn_orient_matrix_UB_12      0.0890998000
_diffrn_orient_matrix_UB_13      0.0857244000
_diffrn_orient_matrix_UB_21      0.0438989000
_diffrn_orient_matrix_UB_22      0.1431481000
_diffrn_orient_matrix_UB_23      -0.0642128000
_diffrn_orient_matrix_UB_31      -0.0399387000
_diffrn_orient_matrix_UB_32      0.1365526000
_diffrn_orient_matrix_UB_33      0.1310749000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10725
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.352
_diffrn_reflns_theta_min         4.859
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0358P)²+0.0948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.823
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                4220
_reflns_number_total             4256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np1c00681_si_003.cif
_cod_data_source_block           liangxiao_lx-t-30_collect
_cod_database_code               1565111
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C26 H29 O10 '
_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.
;
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.914
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C14(H14), C13(H13), C23(H23), C22(H22), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C25(H25A,H25B,H25C), C18(H18A,H18B,
 H18C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O19(H19), O33(H33)
;
_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.876
loop_
_space_group_symop_operation_xyz
'x, y, z'
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
O15 O 0.60766(16) 0.71360(17) 0.51186(14) 0.0159(3) Uani 1 1 d . . . . .
O1 O 0.90391(17) 0.78364(18) 0.82917(14) 0.0199(3) Uani 1 1 d . . . . .
O19 O 0.27023(17) 0.68801(19) 0.63310(15) 0.0205(3) Uani 1 1 d . . . . .
H19 H 0.1745 0.6424 0.6511 0.031 Uiso 1 1 calc GR . . . .
O24 O 0.42666(19) 0.6462(2) 0.90716(15) 0.0243(3) Uani 1 1 d . . . . .
O12 O 0.93551(17) 0.51174(19) 0.69655(15) 0.0201(3) Uani 1 1 d . . . . .
O27 O 0.25556(18) 0.56050(19) 0.20728(15) 0.0204(3) Uani 1 1 d . . . . .
O22 O 0.5824(2) 0.8864(2) 0.86238(15) 0.0254(3) Uani 1 1 d . . . . .
O33 O 0.4726(2) 0.4359(2) 0.04837(15) 0.0255(3) Uani 1 1 d . . . . .
H33 H 0.4448 0.4964 0.0112 0.038 Uiso 1 1 calc GR . . . .
O13 O 0.84920(19) 0.2779(2) 0.46963(17) 0.0269(3) Uani 1 1 d . . . . .
O36 O 0.0174(2) 0.4256(2) 0.01776(17) 0.0322(4) Uani 1 1 d . . . . .
C10 C 0.6703(2) 0.6981(2) 0.6338(2) 0.0143(3) Uani 1 1 d . . . . .
C14 C 0.4206(2) 0.6386(2) 0.4414(2) 0.0152(3) Uani 1 1 d . . . . .
H14 H 0.3955 0.7464 0.4479 0.018 Uiso 1 1 calc R . . . .
C11 C 0.5494(2) 0.5776(2) 0.69350(19) 0.0139(4) Uani 1 1 d . . . . .
C9 C 0.8430(2) 0.7980(3) 0.7025(2) 0.0172(4) Uani 1 1 d . . . . .
C20 C 0.5104(3) 0.7050(3) 0.8312(2) 0.0181(4) Uani 1 1 d . . . . .
C12 C 0.3716(2) 0.4321(3) 0.5716(2) 0.0146(3) Uani 1 1 d . . . . .
C13 C 0.2947(2) 0.5447(3) 0.5165(2) 0.0165(4) Uani 1 1 d . . . . .
H13 H 0.1786 0.4579 0.4453 0.020 Uiso 1 1 calc R . . . .
C8 C 0.8122(2) 0.3513(3) 0.5817(2) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.2889(2) 0.2004(3) 0.2972(2) 0.0180(4) Uani 1 1 d . . . . .
C23 C 0.8515(2) 0.5968(3) 0.8064(2) 0.0173(4) Uani 1 1 d . . . . .
H23 H 0.8939 0.5946 0.8982 0.021 Uiso 1 1 calc R . . . .
C17 C 0.6314(3) 0.7587(3) 0.2369(2) 0.0217(4) Uani 1 1 d . . . . .
H17A H 0.7205 0.7772 0.1830 0.033 Uiso 1 1 calc GR . . . .
H17B H 0.6865 0.8346 0.3402 0.033 Uiso 1 1 calc GR . . . .
H17C H 0.5406 0.7945 0.2079 0.033 Uiso 1 1 calc GR . . . .
C22 C 0.6474(2) 0.4739(2) 0.7453(2) 0.0144(3) Uani 1 1 d . . . . .
H22 H 0.5993 0.4499 0.8236 0.017 Uiso 1 1 calc R . . . .
C19 C 0.2319(2) 0.3168(3) 0.6267(2) 0.0197(4) Uani 1 1 d . . . . .
H19A H 0.2872 0.2671 0.6784 0.029 Uiso 1 1 calc GR . . . .
H19B H 0.1364 0.2149 0.5445 0.029 Uiso 1 1 calc GR . . . .
H19C H 0.1846 0.3962 0.6916 0.029 Uiso 1 1 calc GR . . . .
C6 C 0.4805(2) 0.1721(2) 0.4911(2) 0.0165(4) Uani 1 1 d . . . . .
H6A H 0.5125 0.0901 0.4112 0.020 Uiso 1 1 calc R . . . .
H6B H 0.3797 0.0939 0.5129 0.020 Uiso 1 1 calc R . . . .
C16 C 0.5462(3) 0.5511(3) 0.2044(2) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.3823(2) 0.5084(2) 0.2741(2) 0.0166(4) Uani 1 1 d . . . . .
C1 C 0.1230(3) 0.4078(3) 0.0944(2) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.6394(2) 0.2868(2) 0.6267(2) 0.0156(4) Uani 1 1 d . . . . .
C3 C 0.2741(2) 0.2975(3) 0.2237(2) 0.0197(4) Uani 1 1 d . . . . .
C5 C 0.4268(2) 0.3015(2) 0.4443(2) 0.0150(4) Uani 1 1 d . . . . .
H5 H 0.5355 0.3845 0.4321 0.018 Uiso 1 1 calc R . . . .
C25 C 0.1689(3) -0.0065(3) 0.2394(2) 0.0269(5) Uani 1 1 d . . . . .
H25A H 0.1006 -0.0243 0.3082 0.040 Uiso 1 1 calc GR . . . .
H25B H 0.2410 -0.0771 0.2268 0.040 Uiso 1 1 calc GR . . . .
H25C H 0.0888 -0.0495 0.1467 0.040 Uiso 1 1 calc GR . . . .
C18 C 0.6878(3) 0.4889(3) 0.2459(2) 0.0228(4) Uani 1 1 d . . . . .
H18A H 0.6311 0.3604 0.2296 0.034 Uiso 1 1 calc GR . . . .
H18B H 0.7500 0.5677 0.3477 0.034 Uiso 1 1 calc GR . . . .
H18C H 0.7716 0.4993 0.1865 0.034 Uiso 1 1 calc GR . . . .
C21 C 0.9819(3) 0.9330(3) 0.6686(2) 0.0218(4) Uani 1 1 d . . . . .
H21A H 1.0175 1.0584 0.7445 0.033 Uiso 1 1 calc GR . . . .
H21B H 0.9341 0.9255 0.5761 0.033 Uiso 1 1 calc GR . . . .
H21C H 1.0841 0.9023 0.6633 0.033 Uiso 1 1 calc GR . . . .
C24 C 0.6568(3) 0.1625(3) 0.7001(2) 0.0215(4) Uani 1 1 d . . . . .
H24A H 0.6707 0.0556 0.6306 0.032 Uiso 1 1 calc GR . . . .
H24B H 0.5510 0.1200 0.7326 0.032 Uiso 1 1 calc GR . . . .
H24C H 0.7596 0.2343 0.7829 0.032 Uiso 1 1 calc GR . . . .
C2 C 0.1293(3) 0.2294(3) 0.0890(2) 0.0265(4) Uani 1 1 d . . . . .
H2A H 0.0152 0.1471 0.0928 0.032 Uiso 1 1 calc R . . . .
H2B H 0.1596 0.1622 0.0004 0.032 Uiso 1 1 calc R . . . .
C26 C 0.5347(5) 1.0072(4) 0.9816(3) 0.0450(7) Uani 1 1 d . . . . .
H26A H 0.4066 0.9626 0.9615 0.067 Uiso 1 1 calc GR . . . .
H26B H 0.5857 1.1333 0.9915 0.067 Uiso 1 1 calc GR . . . .
H26C H 0.5799 1.0063 1.0711 0.067 Uiso 1 1 calc GR . . . .
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_
_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 O15 C14 123.58(13) . . ?
C23 O1 C9 112.80(14) . . ?
C13 O19 H19 109.5 . . ?
C8 O12 C23 111.33(14) . . ?
C1 O27 C15 111.76(14) . . ?
C20 O22 C26 115.38(17) . . ?
C16 O33 H33 109.5 . . ?
O15 C10 C11 122.48(14) . . ?
C9 C10 O15 117.82(15) . . ?
C9 C10 C11 119.67(15) . . ?
O15 C14 H14 106.3 . . ?
O15 C14 C13 114.26(13) . . ?
O15 C14 C15 110.44(14) . . ?
C13 C14 H14 106.3 . . ?
C13 C14 C15 112.65(14) . . ?
C15 C14 H14 106.3 . . ?
C10 C11 C20 109.38(15) . . ?
C10 C11 C12 109.28(13) . . ?
C10 C11 C22 110.01(14) . . ?
C20 C11 C12 111.02(14) . . ?
C20 C11 C22 106.35(13) . . ?
C12 C11 C22 110.76(13) . . ?
O1 C9 C21 114.32(15) . . ?
C10 C9 O1 117.01(15) . . ?
C10 C9 C21 128.58(16) . . ?
O24 C20 O22 122.86(19) . . ?
O24 C20 C11 123.27(17) . . ?
O22 C20 C11 113.82(15) . . ?
C13 C12 C11 107.16(13) . . ?
C13 C12 C5 109.52(14) . . ?
C19 C12 C11 113.16(15) . . ?
C19 C12 C13 109.64(15) . . ?
C19 C12 C5 111.08(15) . . ?
C5 C12 C11 106.13(14) . . ?
O19 C13 C14 107.79(14) . . ?
O19 C13 C12 111.98(15) . . ?
O19 C13 H13 108.8 . . ?
C14 C13 C12 110.56(14) . . ?
C14 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
O12 C8 C7 109.06(16) . . ?
O13 C8 O12 121.42(17) . . ?
O13 C8 C7 129.43(18) . . ?
C3 C4 C5 119.12(16) . . ?
C3 C4 C25 121.56(16) . . ?
C25 C4 C5 119.31(16) . . ?
O1 C23 O12 106.90(14) . . ?
O1 C23 H23 109.6 . . ?
O1 C23 C22 114.79(14) . . ?
O12 C23 H23 109.6 . . ?
O12 C23 C22 106.30(14) . . ?
C22 C23 H23 109.6 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
C11 C22 H22 108.6 . . ?
C23 C22 C11 110.90(14) . . ?
C23 C22 H22 108.6 . . ?
C23 C22 C7 102.56(14) . . ?
C7 C22 C11 117.22(14) . . ?
C7 C22 H22 108.6 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 C7 110.67(14) . . ?
O33 C16 C17 109.62(14) . . ?
O33 C16 C15 105.25(15) . . ?
O33 C16 C18 104.95(16) . . ?
C17 C16 C15 111.36(15) . . ?
C18 C16 C17 110.67(16) . . ?
C18 C16 C15 114.56(14) . . ?
O27 C15 C14 102.20(14) . . ?
O27 C15 C16 105.11(13) . . ?
O27 C15 C3 102.62(13) . . ?
C14 C15 C16 115.52(14) . . ?
C3 C15 C14 115.95(14) . . ?
C3 C15 C16 113.15(15) . . ?
O27 C1 C2 110.33(15) . . ?
O36 C1 O27 120.86(18) . . ?
O36 C1 C2 128.77(19) . . ?
C8 C7 C22 102.50(14) . . ?
C8 C7 C6 109.88(15) . . ?
C8 C7 C24 106.32(14) . . ?
C6 C7 C22 118.05(15) . . ?
C6 C7 C24 110.11(14) . . ?
C24 C7 C22 109.17(15) . . ?
C4 C3 C15 126.19(16) . . ?
C4 C3 C2 126.40(17) . . ?
C2 C3 C15 106.74(15) . . ?
C12 C5 H5 106.2 . . ?
C4 C5 C12 113.30(15) . . ?
C4 C5 C6 114.29(15) . . ?
C4 C5 H5 106.2 . . ?
C6 C5 C12 109.93(15) . . ?
C6 C5 H5 106.2 . . ?
C4 C25 H25A 109.5 . . ?
C4 C25 H25B 109.5 . . ?
C4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 C24 H24A 109.5 . . ?
C7 C24 H24B 109.5 . . ?
C7 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 C1 103.71(16) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O22 C26 H26A 109.5 . . ?
O22 C26 H26B 109.5 . . ?
O22 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O15 C10 1.375(2) . ?
O15 C14 1.437(2) . ?
O1 C9 1.409(2) . ?
O1 C23 1.400(2) . ?
O19 H19 0.8200 . ?
O19 C13 1.421(2) . ?
O24 C20 1.214(2) . ?
O12 C8 1.362(2) . ?
O12 C23 1.451(2) . ?
O27 C15 1.472(2) . ?
O27 C1 1.357(2) . ?
O22 C20 1.329(2) . ?
O22 C26 1.440(3) . ?
O33 H33 0.8200 . ?
O33 C16 1.441(2) . ?
O13 C8 1.195(3) . ?
O36 C1 1.204(3) . ?
C10 C11 1.511(2) . ?
C10 C9 1.327(2) . ?
C14 H14 0.9800 . ?
C14 C13 1.526(2) . ?
C14 C15 1.563(3) . ?
C11 C20 1.544(3) . ?
C11 C12 1.568(2) . ?
C11 C22 1.570(2) . ?
C9 C21 1.483(3) . ?
C12 C13 1.544(2) . ?
C12 C19 1.532(2) . ?
C12 C5 1.566(3) . ?
C13 H13 0.9800 . ?
C8 C7 1.516(2) . ?
C4 C3 1.334(3) . ?
C4 C5 1.521(2) . ?
C4 C25 1.514(3) . ?
C23 H23 0.9800 . ?
C23 C22 1.548(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C16 1.529(2) . ?
C22 H22 0.9800 . ?
C22 C7 1.550(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.528(2) . ?
C6 C5 1.521(2) . ?
C16 C15 1.575(3) . ?
C16 C18 1.522(3) . ?
C15 C3 1.532(2) . ?
C1 C2 1.506(3) . ?
C7 C24 1.541(2) . ?
C3 C2 1.505(3) . ?
C5 H5 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
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
O15 C10 C11 C20 -103.16(19) . . . . ?
O15 C10 C11 C12 18.6(2) . . . . ?
O15 C10 C11 C22 140.38(17) . . . . ?
O15 C10 C9 O1 178.57(16) . . . . ?
O15 C10 C9 C21 2.1(3) . . . . ?
O15 C14 C13 O19 83.62(17) . . . . ?
O15 C14 C13 C12 -39.1(2) . . . . ?
O15 C14 C15 O27 -138.93(13) . . . . ?
O15 C14 C15 C16 -25.44(19) . . . . ?
O15 C14 C15 C3 110.35(16) . . . . ?
O1 C23 C22 C11 11.2(2) . . . . ?
O1 C23 C22 C7 137.13(15) . . . . ?
O12 C8 C7 C22 27.38(17) . . . . ?
O12 C8 C7 C6 153.69(14) . . . . ?
O12 C8 C7 C24 -87.17(17) . . . . ?
O12 C23 C22 C11 -106.75(16) . . . . ?
O12 C23 C22 C7 19.18(16) . . . . ?
O27 C15 C3 C4 -149.12(19) . . . . ?
O27 C15 C3 C2 21.9(2) . . . . ?
O27 C1 C2 C3 5.1(2) . . . . ?
O33 C16 C15 O27 -59.32(17) . . . . ?
O33 C16 C15 C14 -171.13(14) . . . . ?
O33 C16 C15 C3 51.87(18) . . . . ?
O13 C8 C7 C22 -156.21(19) . . . . ?
O13 C8 C7 C6 -29.9(3) . . . . ?
O13 C8 C7 C24 89.2(2) . . . . ?
O36 C1 C2 C3 -172.5(2) . . . . ?
C10 O15 C14 C13 1.9(2) . . . . ?
C10 O15 C14 C15 -126.30(17) . . . . ?
C10 C11 C20 O24 -174.80(17) . . . . ?
C10 C11 C20 O22 3.0(2) . . . . ?
C10 C11 C12 C13 -53.03(19) . . . . ?
C10 C11 C12 C19 -174.01(16) . . . . ?
C10 C11 C12 C5 63.92(17) . . . . ?
C10 C11 C22 C23 33.1(2) . . . . ?
C10 C11 C22 C7 -84.16(18) . . . . ?
C14 O15 C10 C11 8.5(3) . . . . ?
C14 O15 C10 C9 -169.52(16) . . . . ?
C14 C15 C3 C4 -38.6(3) . . . . ?
C14 C15 C3 C2 132.39(18) . . . . ?
C11 C10 C9 O1 0.5(3) . . . . ?
C11 C10 C9 C21 -176.0(2) . . . . ?
C11 C12 C13 O19 -55.44(18) . . . . ?
C11 C12 C13 C14 64.78(18) . . . . ?
C11 C12 C5 C4 -159.00(14) . . . . ?
C11 C12 C5 C6 71.77(16) . . . . ?
C11 C22 C7 C8 94.62(17) . . . . ?
C11 C22 C7 C6 -26.2(2) . . . . ?
C11 C22 C7 C24 -152.93(15) . . . . ?
C9 O1 C23 O12 63.10(17) . . . . ?
C9 O1 C23 C22 -54.5(2) . . . . ?
C9 C10 C11 C20 74.9(2) . . . . ?
C9 C10 C11 C12 -163.41(17) . . . . ?
C9 C10 C11 C22 -41.6(2) . . . . ?
C20 C11 C12 C13 67.70(17) . . . . ?
C20 C11 C12 C19 -53.28(19) . . . . ?
C20 C11 C12 C5 -175.35(13) . . . . ?
C20 C11 C22 C23 -85.24(18) . . . . ?
C20 C11 C22 C7 157.49(14) . . . . ?
C12 C11 C20 O24 64.5(2) . . . . ?
C12 C11 C20 O22 -117.71(16) . . . . ?
C12 C11 C22 C23 154.03(15) . . . . ?
C12 C11 C22 C7 36.8(2) . . . . ?
C13 C14 C15 O27 91.97(15) . . . . ?
C13 C14 C15 C16 -154.53(14) . . . . ?
C13 C14 C15 C3 -18.7(2) . . . . ?
C13 C12 C5 C4 -43.64(18) . . . . ?
C13 C12 C5 C6 -172.87(14) . . . . ?
C8 O12 C23 O1 -125.75(15) . . . . ?
C8 O12 C23 C22 -2.70(18) . . . . ?
C4 C3 C2 C1 154.1(2) . . . . ?
C23 O1 C9 C10 50.2(2) . . . . ?
C23 O1 C9 C21 -132.88(17) . . . . ?
C23 O12 C8 O13 167.35(16) . . . . ?
C23 O12 C8 C7 -15.89(19) . . . . ?
C23 C22 C7 C8 -27.09(16) . . . . ?
C23 C22 C7 C6 -147.93(15) . . . . ?
C23 C22 C7 C24 85.36(16) . . . . ?
C17 C16 C15 O27 59.38(18) . . . . ?
C17 C16 C15 C14 -52.42(19) . . . . ?
C17 C16 C15 C3 170.58(15) . . . . ?
C22 C11 C20 O24 -56.0(2) . . . . ?
C22 C11 C20 O22 121.72(16) . . . . ?
C22 C11 C12 C13 -174.38(15) . . . . ?
C22 C11 C12 C19 64.64(19) . . . . ?
C22 C11 C12 C5 -57.43(17) . . . . ?
C19 C12 C13 O19 67.73(19) . . . . ?
C19 C12 C13 C14 -172.04(16) . . . . ?
C19 C12 C5 C4 77.62(18) . . . . ?
C19 C12 C5 C6 -51.62(18) . . . . ?
C16 C15 C3 C4 98.2(2) . . . . ?
C16 C15 C3 C2 -90.80(19) . . . . ?
C15 O27 C1 O36 -172.65(19) . . . . ?
C15 O27 C1 C2 9.5(2) . . . . ?
C15 C14 C13 O19 -149.29(14) . . . . ?
C15 C14 C13 C12 88.01(18) . . . . ?
C15 C3 C2 C1 -16.9(2) . . . . ?
C1 O27 C15 C14 -140.02(15) . . . . ?
C1 O27 C15 C16 98.98(17) . . . . ?
C1 O27 C15 C3 -19.6(2) . . . . ?
C7 C6 C5 C12 -60.18(18) . . . . ?
C7 C6 C5 C4 171.13(15) . . . . ?
C3 C4 C5 C12 74.2(2) . . . . ?
C3 C4 C5 C6 -158.78(18) . . . . ?
C5 C12 C13 O19 -170.14(13) . . . . ?
C5 C12 C13 C14 -49.92(18) . . . . ?
C5 C4 C3 C15 -1.2(3) . . . . ?
C5 C4 C3 C2 -170.5(2) . . . . ?
C5 C6 C7 C8 -80.11(19) . . . . ?
C5 C6 C7 C22 36.8(2) . . . . ?
C5 C6 C7 C24 163.10(15) . . . . ?
C25 C4 C3 C15 177.30(19) . . . . ?
C25 C4 C3 C2 8.0(3) . . . . ?
C25 C4 C5 C12 -104.3(2) . . . . ?
C25 C4 C5 C6 22.7(3) . . . . ?
C18 C16 C15 O27 -174.06(15) . . . . ?
C18 C16 C15 C14 74.13(19) . . . . ?
C18 C16 C15 C3 -62.9(2) . . . . ?
C26 O22 C20 O24 -8.0(3) . . . . ?
C26 O22 C20 C11 174.26(18) . . . . ?
