#------------------------------------------------------------------------------
#$Date: 2021-11-04 02:35:51 +0200 (Thu, 04 Nov 2021) $
#$Revision: 270284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565113.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_1565113
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 O9, C H4 O'
_chemical_formula_sum            'C27 H36 O10'
_chemical_formula_weight         520.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.32300(10)
_cell_length_b                   13.9278(2)
_cell_length_c                   11.0616(2)
_cell_measurement_reflns_used    10981
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      73.5260
_cell_measurement_theta_min      5.2120
_cell_volume                     1240.66(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      99.9(5)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -26.00  28.00   0.50    0.50    --    0.00 -82.00  30.00  108
  2  ω    -23.00   3.00   0.50    0.50    --    0.00 -82.00-120.00   52
  3  ω    -28.00  27.00   0.50    0.50    --    0.00 -82.00-150.00  110
  4  ω    -32.00  31.00   0.50    0.50    --    0.00 -82.00 -60.00  126
  5  ω    -28.00  31.00   0.50    0.50    --    0.00 -82.00 150.00  118
  6  ω     76.00 173.00   0.50    2.00    --   95.20  15.00 -60.00  194
  7  ω    118.00 144.00   0.50    2.00    --   95.20  45.00  90.00   52
  8  ω      7.00  49.00   0.50    2.00    --   95.20 -77.00   0.00   84
  9  ω     16.00 111.00   0.50    2.00    --   95.20 -61.00  30.00  190
 10  ω     82.00 137.00   0.50    2.00    --   95.20  77.00  60.00  110
 11  ω      8.00  49.00   0.50    2.00    --   95.20 -30.00 120.00   82
 12  ω     76.00 181.00   0.50    2.00    --   95.20  45.00  60.00  210
 13  ω     76.00 102.00   0.50    2.00    --   95.20  45.00  90.00   52
 14  ω     79.00 104.00   0.50    2.00    --   95.20  61.00-120.00   50
 15  ω     80.00 156.00   0.50    2.00    --   95.20  45.00 120.00  152
 16  ω      6.00 123.00   0.50    2.00    --   95.20 -77.00  30.00  234
 17  ω    109.00 146.00   0.50    2.00    --   95.20  61.00-120.00   74
 18  ω     76.00 176.00   0.50    2.00    --   95.20  45.00 150.00  200
 19  ω      6.00 119.00   0.50    2.00    --   95.20 -15.00   0.00  226
 20  ω    149.00 178.00   0.50    2.00    --   95.20  77.00  60.00   58
 21  ω    109.00 149.00   0.50    2.00    --   95.20  15.00  60.00   80
;
_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      -0.1687684000
_diffrn_orient_matrix_UB_12      0.0186429000
_diffrn_orient_matrix_UB_13      -0.0932426000
_diffrn_orient_matrix_UB_21      0.0652626000
_diffrn_orient_matrix_UB_22      0.0966169000
_diffrn_orient_matrix_UB_23      -0.0360541000
_diffrn_orient_matrix_UB_31      0.0618883000
_diffrn_orient_matrix_UB_32      -0.0505341000
_diffrn_orient_matrix_UB_33      -0.1036426000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11578
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.979
_diffrn_reflns_theta_min         5.212
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82341
_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    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4843
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0589P)²+0.3398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                4753
_reflns_number_total             4843
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np1c00681_si_002.cif
_cod_data_source_block           liangxiao_lx-t-6_collect
_cod_database_code               1565113
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C48 H72 N6 O20 '
_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   0.933
_shelx_estimated_absorpt_t_min   0.843
_reflns_odcompleteness_completeness 99.91
_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), C5(H5), C23(H23), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C25(H25A,H25B,H25C), C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.687
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O9 O 0.0393(2) 0.39765(13) 0.14404(16) 0.0231(4) Uani 1 1 d . . . . .
O5 O 0.0839(2) 0.46090(12) 0.46635(16) 0.0208(4) Uani 1 1 d . . . . .
O4 O 0.1756(2) 0.57826(12) 0.76199(15) 0.0195(4) Uani 1 1 d . . . . .
O2 O 0.2979(2) 0.41147(13) 0.85177(16) 0.0233(4) Uani 1 1 d . . . . .
H2 H 0.3867 0.3829 0.8635 0.035 Uiso 1 1 calc GR . . . .
O6 O 0.3036(2) 0.33570(13) 0.18295(18) 0.0237(4) Uani 1 1 d . . . . .
O3 O 0.2755(3) 0.65635(14) 0.94019(17) 0.0272(4) Uani 1 1 d . . . . .
O7 O 0.5319(2) 0.30625(14) 0.33452(19) 0.0286(4) Uani 1 1 d . . . . .
O10 O -0.0965(2) 0.62182(14) 0.24613(18) 0.0285(4) Uani 1 1 d . . . . .
O8 O 0.0556(2) 0.63945(15) 0.10764(18) 0.0282(4) Uani 1 1 d . . . . .
O1 O 0.5868(3) 0.31243(19) 0.9179(2) 0.0406(6) Uani 1 1 d . . . . .
C1 C 0.3022(3) 0.61255(18) 0.8522(2) 0.0209(5) Uani 1 1 d . . . . .
C10 C 0.0932(3) 0.46437(18) 0.3439(2) 0.0178(5) Uani 1 1 d . . . . .
C9 C 0.0287(3) 0.39200(18) 0.2689(2) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.4402(3) 0.36400(19) 0.2710(2) 0.0215(5) Uani 1 1 d . . . . .
C16 C 0.2173(3) 0.41166(18) 0.7205(2) 0.0200(5) Uani 1 1 d . . . . .
C2 C 0.4655(3) 0.59354(18) 0.8235(2) 0.0207(5) Uani 1 1 d . . . . .
H2A H 0.5316 0.5486 0.8827 0.025 Uiso 1 1 calc R . . . .
H2B H 0.5280 0.6525 0.8244 0.025 Uiso 1 1 calc R . . . .
C12 C 0.2853(3) 0.60326(18) 0.4045(2) 0.0174(5) Uani 1 1 d . . . . .
C3 C 0.4156(3) 0.55103(17) 0.6942(2) 0.0182(5) Uani 1 1 d . . . . .
C20 C 0.0297(3) 0.60714(18) 0.2141(2) 0.0221(5) Uani 1 1 d . . . . .
C15 C 0.2361(3) 0.51673(17) 0.6741(2) 0.0177(5) Uani 1 1 d . . . . .
C14 C 0.1141(3) 0.54383(17) 0.5473(2) 0.0181(5) Uani 1 1 d . . . . .
H14 H 0.0081 0.5608 0.5650 0.022 Uiso 1 1 calc R . . . .
C5 C 0.4239(3) 0.53092(17) 0.4733(2) 0.0175(5) Uani 1 1 d . . . . .
H5 H 0.3679 0.4695 0.4773 0.021 Uiso 1 1 calc R . . . .
C23 C 0.2000(3) 0.41744(19) 0.1320(2) 0.0216(5) Uani 1 1 d . . . . .
H23 H 0.1970 0.4246 0.0433 0.026 Uiso 1 1 calc R . . . .
C6 C 0.5470(3) 0.51344(18) 0.3941(2) 0.0192(5) Uani 1 1 d . . . . .
H6A H 0.6323 0.4692 0.4374 0.023 Uiso 1 1 calc R . . . .
H6B H 0.6005 0.5735 0.3830 0.023 Uiso 1 1 calc R . . . .
C13 C 0.1720(3) 0.63119(17) 0.4880(2) 0.0179(5) Uani 1 1 d . . . . .
H13A H 0.2314 0.6741 0.5533 0.021 Uiso 1 1 calc R . . . .
H13B H 0.0762 0.6654 0.4387 0.021 Uiso 1 1 calc R . . . .
C24 C 0.5705(3) 0.4878(2) 0.1737(2) 0.0242(5) Uani 1 1 d . . . . .
H24A H 0.6797 0.4628 0.2093 0.036 Uiso 1 1 calc GR . . . .
H24B H 0.5776 0.5552 0.1579 0.036 Uiso 1 1 calc GR . . . .
H24C H 0.5222 0.4551 0.0966 0.036 Uiso 1 1 calc GR . . . .
C4 C 0.5019(3) 0.56040(18) 0.6078(2) 0.0191(5) Uani 1 1 d . . . . .
C22 C 0.2820(3) 0.50685(17) 0.2040(2) 0.0186(5) Uani 1 1 d . . . . .
H22 H 0.2882 0.5571 0.1433 0.022 Uiso 1 1 calc R . . . .
C21 C -0.0577(3) 0.3054(2) 0.2982(3) 0.0267(6) Uani 1 1 d . . . . .
H21A H -0.1639 0.2996 0.2392 0.040 Uiso 1 1 calc GR . . . .
H21B H -0.0731 0.3109 0.3811 0.040 Uiso 1 1 calc GR . . . .
H21C H 0.0079 0.2495 0.2933 0.040 Uiso 1 1 calc GR . . . .
C18 C 0.0349(3) 0.38793(19) 0.7098(3) 0.0244(5) Uani 1 1 d . . . . .
H18A H 0.0265 0.3243 0.7411 0.037 Uiso 1 1 calc GR . . . .
H18B H -0.0261 0.3912 0.6238 0.037 Uiso 1 1 calc GR . . . .
H18C H -0.0101 0.4333 0.7577 0.037 Uiso 1 1 calc GR . . . .
C11 C 0.1764(3) 0.54573(17) 0.2922(2) 0.0181(5) Uani 1 1 d . . . . .
C19 C 0.3554(3) 0.69494(18) 0.3620(2) 0.0217(5) Uani 1 1 d . . . . .
H19A H 0.4319 0.7241 0.4321 0.033 Uiso 1 1 calc GR . . . .
H19B H 0.2663 0.7388 0.3284 0.033 Uiso 1 1 calc GR . . . .
H19C H 0.4121 0.6796 0.2990 0.033 Uiso 1 1 calc GR . . . .
C7 C 0.4608(3) 0.47189(18) 0.2658(2) 0.0191(5) Uani 1 1 d . . . . .
C25 C 0.6743(3) 0.6024(2) 0.6388(2) 0.0248(5) Uani 1 1 d . . . . .
H25A H 0.7011 0.6269 0.7226 0.037 Uiso 1 1 calc GR . . . .
H25B H 0.6790 0.6536 0.5817 0.037 Uiso 1 1 calc GR . . . .
H25C H 0.7526 0.5534 0.6318 0.037 Uiso 1 1 calc GR . . . .
C17 C 0.2982(3) 0.33639(18) 0.6549(3) 0.0221(5) Uani 1 1 d . . . . .
H17A H 0.4111 0.3544 0.6603 0.033 Uiso 1 1 calc GR . . . .
H17B H 0.2381 0.3322 0.5687 0.033 Uiso 1 1 calc GR . . . .
H17C H 0.2961 0.2752 0.6944 0.033 Uiso 1 1 calc GR . . . .
C26 C -0.0848(4) 0.6864(2) 0.0229(3) 0.0328(6) Uani 1 1 d . . . . .
H26A H -0.0518 0.7097 -0.0489 0.049 Uiso 1 1 calc GR . . . .
H26B H -0.1214 0.7392 0.0649 0.049 Uiso 1 1 calc GR . . . .
H26C H -0.1740 0.6412 -0.0034 0.049 Uiso 1 1 calc GR . . . .
C27 C 0.7246(4) 0.3641(2) 0.8993(3) 0.0348(6) Uani 1 1 d . . . . .
H27A H 0.6923 0.3994 0.8224 0.052 Uiso 1 1 calc GR . . . .
H27B H 0.8120 0.3201 0.8955 0.052 Uiso 1 1 calc GR . . . .
H27C H 0.7633 0.4079 0.9674 0.052 Uiso 1 1 calc GR . . . .
H1 H 0.619(7) 0.255(5) 0.975(6) 0.088(18) Uiso 1 1 d . . . . .
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
C23 O9 C9 113.67(19) . . ?
C10 O5 C14 122.50(19) . . ?
C1 O4 C15 111.19(19) . . ?
C16 O2 H2 109.5 . . ?
C8 O6 C23 111.03(19) . . ?
C20 O8 C26 116.1(2) . . ?
C27 O1 H1 113(3) . . ?
O4 C1 C2 111.3(2) . . ?
O3 C1 O4 120.4(2) . . ?
O3 C1 C2 128.2(2) . . ?
O5 C10 C11 122.9(2) . . ?
C9 C10 O5 118.2(2) . . ?
C9 C10 C11 118.9(2) . . ?
O9 C9 C21 114.5(2) . . ?
C10 C9 O9 117.0(2) . . ?
C10 C9 C21 128.5(2) . . ?
O6 C8 C7 110.1(2) . . ?
O7 C8 O6 121.2(2) . . ?
O7 C8 C7 128.6(2) . . ?
O2 C16 C15 105.8(2) . . ?
O2 C16 C18 106.2(2) . . ?
O2 C16 C17 109.3(2) . . ?
C18 C16 C15 110.8(2) . . ?
C17 C16 C15 113.06(19) . . ?
C17 C16 C18 111.3(2) . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C1 C2 C3 102.9(2) . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C13 C12 C5 111.01(19) . . ?
C13 C12 C11 106.80(19) . . ?
C11 C12 C5 105.27(19) . . ?
C19 C12 C5 113.20(19) . . ?
C19 C12 C13 108.4(2) . . ?
C19 C12 C11 112.02(19) . . ?
C2 C3 C15 106.6(2) . . ?
C4 C3 C2 124.8(2) . . ?
C4 C3 C15 127.4(2) . . ?
O10 C20 O8 123.4(2) . . ?
O10 C20 C11 123.2(2) . . ?
O8 C20 C11 113.4(2) . . ?
O4 C15 C16 104.24(18) . . ?
O4 C15 C3 101.89(18) . . ?
O4 C15 C14 101.49(18) . . ?
C3 C15 C16 114.7(2) . . ?
C3 C15 C14 116.50(19) . . ?
C14 C15 C16 115.1(2) . . ?
O5 C14 C15 109.66(19) . . ?
O5 C14 H14 107.1 . . ?
O5 C14 C13 113.48(18) . . ?
C15 C14 H14 107.1 . . ?
C13 C14 C15 112.2(2) . . ?
C13 C14 H14 107.1 . . ?
C12 C5 H5 106.4 . . ?
C6 C5 C12 109.87(19) . . ?
C6 C5 H5 106.4 . . ?
C4 C5 C12 112.32(19) . . ?
C4 C5 H5 106.4 . . ?
C4 C5 C6 114.9(2) . . ?
O9 C23 O6 107.2(2) . . ?
O9 C23 H23 109.3 . . ?
O9 C23 C22 114.7(2) . . ?
O6 C23 H23 109.3 . . ?
O6 C23 C22 106.89(19) . . ?
C22 C23 H23 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.5(2) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 C12 111.66(19) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C24 H24A 109.5 . . ?
C7 C24 H24B 109.5 . . ?
C7 C24 H24C 109.5 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 C25 121.8(2) . . ?
C25 C4 C5 118.3(2) . . ?
C23 C22 H22 108.4 . . ?
C23 C22 C11 110.9(2) . . ?
C23 C22 C7 103.0(2) . . ?
C11 C22 H22 108.4 . . ?
C7 C22 H22 108.4 . . ?
C7 C22 C11 117.5(2) . . ?
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 . . ?
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 . . ?
C10 C11 C12 108.22(19) . . ?
C10 C11 C20 104.53(19) . . ?
C10 C11 C22 111.04(19) . . ?
C12 C11 C22 111.64(19) . . ?
C20 C11 C12 112.0(2) . . ?
C20 C11 C22 109.20(19) . . ?
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 . . ?
C8 C7 C6 111.7(2) . . ?
C8 C7 C24 105.0(2) . . ?
C8 C7 C22 102.9(2) . . ?
C6 C7 C24 109.9(2) . . ?
C6 C7 C22 117.5(2) . . ?
C24 C7 C22 109.0(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 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O8 C26 H26A 109.5 . . ?
O8 C26 H26B 109.5 . . ?
O8 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O1 C27 H27A 109.5 . . ?
O1 C27 H27B 109.5 . . ?
O1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
O9 C9 1.408(3) . ?
O9 C23 1.404(3) . ?
O5 C10 1.377(3) . ?
O5 C14 1.444(3) . ?
O4 C1 1.343(3) . ?
O4 C15 1.477(3) . ?
O2 H2 0.8200 . ?
O2 C16 1.437(3) . ?
O6 C8 1.356(3) . ?
O6 C23 1.453(3) . ?
O3 C1 1.216(3) . ?
O7 C8 1.205(3) . ?
O10 C20 1.207(3) . ?
O8 C20 1.329(3) . ?
O8 C26 1.456(3) . ?
O1 C27 1.412(4) . ?
O1 H1 1.01(7) . ?
C1 C2 1.496(3) . ?
C10 C9 1.330(4) . ?
C10 C11 1.513(3) . ?
C9 C21 1.482(4) . ?
C8 C7 1.515(4) . ?
C16 C15 1.572(3) . ?
C16 C18 1.528(4) . ?
C16 C17 1.525(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.506(3) . ?
C12 C5 1.575(3) . ?
C12 C13 1.528(3) . ?
C12 C11 1.561(3) . ?
C12 C19 1.526(3) . ?
C3 C15 1.530(3) . ?
C3 C4 1.339(3) . ?
C20 C11 1.560(3) . ?
C15 C14 1.556(3) . ?
C14 H14 0.9800 . ?
C14 C13 1.517(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.528(3) . ?
C5 C4 1.521(3) . ?
C23 H23 0.9800 . ?
C23 C22 1.542(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.533(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 C7 1.546(3) . ?
C4 C25 1.506(3) . ?
C22 H22 0.9800 . ?
C22 C11 1.566(3) . ?
C22 C7 1.550(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
O9 C23 C22 C11 9.2(3) . . . . ?
O9 C23 C22 C7 135.7(2) . . . . ?
O5 C10 C9 O9 179.7(2) . . . . ?
O5 C10 C9 C21 1.1(4) . . . . ?
O5 C10 C11 C12 15.5(3) . . . . ?
O5 C10 C11 C20 -104.0(2) . . . . ?
O5 C10 C11 C22 138.4(2) . . . . ?
O5 C14 C13 C12 -36.1(3) . . . . ?
O4 C1 C2 C3 5.7(3) . . . . ?
O4 C15 C14 O5 -146.59(18) . . . . ?
O4 C15 C14 C13 86.4(2) . . . . ?
O2 C16 C15 O4 -51.5(2) . . . . ?
O2 C16 C15 C3 59.0(2) . . . . ?
O2 C16 C15 C14 -161.71(19) . . . . ?
O6 C8 C7 C6 150.6(2) . . . . ?
O6 C8 C7 C24 -90.4(2) . . . . ?
O6 C8 C7 C22 23.5(3) . . . . ?
O6 C23 C22 C11 -109.4(2) . . . . ?
O6 C23 C22 C7 17.0(2) . . . . ?
O3 C1 C2 C3 -171.1(3) . . . . ?
O7 C8 C7 C6 -34.6(4) . . . . ?
O7 C8 C7 C24 84.4(3) . . . . ?
O7 C8 C7 C22 -161.6(3) . . . . ?
O10 C20 C11 C10 38.2(3) . . . . ?
O10 C20 C11 C12 -78.7(3) . . . . ?
O10 C20 C11 C22 157.1(2) . . . . ?
O8 C20 C11 C10 -140.1(2) . . . . ?
O8 C20 C11 C12 103.0(2) . . . . ?
O8 C20 C11 C22 -21.2(3) . . . . ?
C1 O4 C15 C16 97.9(2) . . . . ?
C1 O4 C15 C3 -21.7(2) . . . . ?
C1 O4 C15 C14 -142.26(19) . . . . ?
C1 C2 C3 C15 -18.8(2) . . . . ?
C1 C2 C3 C4 149.1(2) . . . . ?
C10 O5 C14 C15 -131.7(2) . . . . ?
C10 O5 C14 C13 -5.4(3) . . . . ?
C9 O9 C23 O6 65.4(2) . . . . ?
C9 O9 C23 C22 -53.1(3) . . . . ?
C9 C10 C11 C12 -163.2(2) . . . . ?
C9 C10 C11 C20 77.2(3) . . . . ?
C9 C10 C11 C22 -40.4(3) . . . . ?
C8 O6 C23 O9 -126.4(2) . . . . ?
C8 O6 C23 C22 -2.9(3) . . . . ?
C16 C15 C14 O5 -34.7(3) . . . . ?
C16 C15 C14 C13 -161.77(19) . . . . ?
C2 C3 C15 O4 24.4(2) . . . . ?
C2 C3 C15 C16 -87.5(2) . . . . ?
C2 C3 C15 C14 133.8(2) . . . . ?
C2 C3 C4 C5 -168.4(2) . . . . ?
C2 C3 C4 C25 9.8(4) . . . . ?
C12 C5 C6 C7 -59.4(3) . . . . ?
C12 C5 C4 C3 72.5(3) . . . . ?
C12 C5 C4 C25 -105.7(3) . . . . ?
C3 C15 C14 O5 103.8(2) . . . . ?
C3 C15 C14 C13 -23.3(3) . . . . ?
C15 O4 C1 O3 -172.3(2) . . . . ?
C15 O4 C1 C2 10.6(3) . . . . ?
C15 C3 C4 C5 -3.0(4) . . . . ?
C15 C3 C4 C25 175.2(2) . . . . ?
C15 C14 C13 C12 88.8(2) . . . . ?
C14 O5 C10 C9 -165.3(2) . . . . ?
C14 O5 C10 C11 15.9(3) . . . . ?
C5 C12 C13 C14 -48.0(3) . . . . ?
C5 C12 C11 C10 64.5(2) . . . . ?
C5 C12 C11 C20 179.15(19) . . . . ?
C5 C12 C11 C22 -58.0(2) . . . . ?
C5 C6 C7 C8 -83.5(3) . . . . ?
C5 C6 C7 C24 160.5(2) . . . . ?
C5 C6 C7 C22 35.1(3) . . . . ?
C23 O9 C9 C10 50.8(3) . . . . ?
C23 O9 C9 C21 -130.4(2) . . . . ?
C23 O6 C8 O7 171.4(2) . . . . ?
C23 O6 C8 C7 -13.3(3) . . . . ?
C23 C22 C11 C10 34.1(3) . . . . ?
C23 C22 C11 C12 154.9(2) . . . . ?
C23 C22 C11 C20 -80.7(2) . . . . ?
C23 C22 C7 C8 -23.5(2) . . . . ?
C23 C22 C7 C6 -146.7(2) . . . . ?
C23 C22 C7 C24 87.5(2) . . . . ?
C6 C5 C4 C3 -160.9(2) . . . . ?
C6 C5 C4 C25 20.9(3) . . . . ?
C13 C12 C5 C6 -173.4(2) . . . . ?
C13 C12 C5 C4 -44.1(3) . . . . ?
C13 C12 C11 C10 -53.6(2) . . . . ?
C13 C12 C11 C20 61.1(2) . . . . ?
C13 C12 C11 C22 -176.10(19) . . . . ?
C4 C3 C15 O4 -143.1(2) . . . . ?
C4 C3 C15 C16 105.0(3) . . . . ?
C4 C3 C15 C14 -33.7(3) . . . . ?
C4 C5 C6 C7 172.7(2) . . . . ?
C18 C16 C15 O4 63.2(2) . . . . ?
C18 C16 C15 C3 173.8(2) . . . . ?
C18 C16 C15 C14 -47.0(3) . . . . ?
C11 C10 C9 O9 -1.4(3) . . . . ?
C11 C10 C9 C21 179.9(2) . . . . ?
C11 C12 C5 C6 71.4(2) . . . . ?
C11 C12 C5 C4 -159.32(19) . . . . ?
C11 C12 C13 C14 66.2(2) . . . . ?
C11 C22 C7 C8 98.6(2) . . . . ?
C11 C22 C7 C6 -24.6(3) . . . . ?
C11 C22 C7 C24 -150.4(2) . . . . ?
C19 C12 C5 C6 -51.2(3) . . . . ?
C19 C12 C5 C4 78.0(2) . . . . ?
C19 C12 C13 C14 -172.9(2) . . . . ?
C19 C12 C11 C10 -172.1(2) . . . . ?
C19 C12 C11 C20 -57.4(3) . . . . ?
C19 C12 C11 C22 65.4(3) . . . . ?
C7 C22 C11 C10 -83.9(3) . . . . ?
C7 C22 C11 C12 36.9(3) . . . . ?
C7 C22 C11 C20 161.3(2) . . . . ?
C17 C16 C15 O4 -171.0(2) . . . . ?
C17 C16 C15 C3 -60.5(3) . . . . ?
C17 C16 C15 C14 78.8(3) . . . . ?
C26 O8 C20 O10 -6.1(4) . . . . ?
C26 O8 C20 C11 172.2(2) . . . . ?
