#------------------------------------------------------------------------------
#$Date: 2021-03-04 04:55:05 +0200 (Thu, 04 Mar 2021) $
#$Revision: 262446 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/02/1560285.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_1560285
loop_
_publ_author_name
'Gao, Ying'
'Duan, Fang-Fang'
'Liu, Lin'
'Peng, Xiao-Gang'
'Meng, Xiang-Gao'
'Ruan, Han-Li'
_publ_section_title
;
 Hypothemycin-Type Resorcylic Acid Lactones with Immunosuppressive
 Activities from a Podospora sp.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              483
_journal_page_last               494
_journal_paper_doi               10.1021/acs.jnatprod.0c01344
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H26 O7'
_chemical_formula_sum            'C19 H26 O7'
_chemical_formula_weight         366.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-25
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 126.110(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.002(2)
_cell_length_b                   5.4539(4)
_cell_length_c                   23.7081(14)
_cell_measurement_reflns_used    1887
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.70
_cell_measurement_theta_min      2.57
_cell_volume                     3656.3(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1543
_diffrn_reflns_av_unetI/netI     0.1693
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15947
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        62.498
_diffrn_reflns_theta_max         62.498
_diffrn_reflns_theta_min         2.307
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.3676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.2006 before and 0.0992 after correction. 
The Ratio of minimum to maximum transmission is 0.4880. 
The λ/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         5264
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0882
_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)+(0.0770P)²+3.4199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2120
_refine_ls_wR_factor_ref         0.2404
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                3634
_reflns_number_total             5264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c01344_si_008.cif
_cod_data_source_block           cu_181220f_0m
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_database_code               1560285
_shelx_shelxl_version_number     2014/7
_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   0.992
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C3(H3), C7(H7), C8(H8), C9(H9), C3A(H3AA), C7A(H7AA), C8A(H8A), C9A(H9A) 
2.b Secondary CH2 refined with riding coordinates: 
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C4A(H4AA,H4AB), 
 C5A(H5AA,H5AB), C6A(H6AA,H6AB), C10A(H10C,H10D) 
2.c Aromatic/amide H refined with riding coordinates: 
 C11(H11), C12(H12), C14(H14), C16(H16), C11A(H11A), C12A(H12A), C14A(H14A), 
 C16A(H16A) 
2.d Tetrahedral OH refined with riding coordinates: 
 O5(H5), O3A(H3AB), O4A(H4AC) 
2.e Idealised Me refined as rotating group: 
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C19A(H19D,H19E,H19F), C20A(H20D, 
 H20E,H20F) 
2.f Idealised tetrahedral OH refined as rotating group: 
 O3(H3A), O4(H4), O7(H7A), O5A(H5AC), O7A(H7AB) 
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
C1 C 0.3577(3) 0.1598(19) 0.0781(5) 0.043(2) Uani 1 1 d . . . . .
C3 C 0.3242(3) 0.405(2) 0.1221(5) 0.049(3) Uani 1 1 d . . . . .
H3 H 0.3165 0.5206 0.0852 0.058 Uiso 1 1 calc R . . . .
C4 C 0.3430(4) 0.545(2) 0.1884(5) 0.055(3) Uani 1 1 d . . . . .
H4A H 0.3210 0.6769 0.1771 0.066 Uiso 1 1 calc R . . . .
H4B H 0.3725 0.6205 0.2027 0.066 Uiso 1 1 calc R . . . .
C5 C 0.3521(3) 0.409(2) 0.2522(5) 0.052(3) Uani 1 1 d . . . . .
H5A H 0.3559 0.5278 0.2857 0.063 Uiso 1 1 calc R . . . .
H5B H 0.3251 0.3071 0.2376 0.063 Uiso 1 1 calc R . . . .
C6 C 0.3965(3) 0.249(2) 0.2873(5) 0.045(2) Uani 1 1 d . . . . .
H6A H 0.3928 0.1341 0.2531 0.054 Uiso 1 1 calc R . . . .
H6B H 0.4234 0.3530 0.3020 0.054 Uiso 1 1 calc R . . . .
C7 C 0.4070(3) 0.1076(17) 0.3497(4) 0.035(2) Uani 1 1 d . . . . .
H7 H 0.3772 0.0319 0.3359 0.042 Uiso 1 1 calc R . . . .
C8 C 0.4427(3) -0.1004(17) 0.3725(4) 0.0307(19) Uani 1 1 d . . . . .
H8 H 0.4307 -0.2089 0.3324 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4937(3) -0.0301(17) 0.4020(4) 0.034(2) Uani 1 1 d . . . . .
H9 H 0.5055 0.0846 0.4408 0.041 Uiso 1 1 calc R . . . .
C10 C 0.5018(3) 0.0790(19) 0.3512(4) 0.039(2) Uani 1 1 d . . . . .
H10A H 0.4896 0.2452 0.3404 0.046 Uiso 1 1 calc R . . . .
H10B H 0.5356 0.0884 0.3740 0.046 Uiso 1 1 calc R . . . .
C11 C 0.4795(3) -0.059(2) 0.2836(4) 0.039(2) Uani 1 1 d . . . . .
H11 H 0.4844 -0.2279 0.2861 0.047 Uiso 1 1 calc R . . . .
C12 C 0.4532(3) 0.043(2) 0.2206(4) 0.039(2) Uani 1 1 d . . . . .
H12 H 0.4457 0.2085 0.2176 0.047 Uiso 1 1 calc R . . . .
C13 C 0.4351(3) -0.0923(19) 0.1547(4) 0.039(2) Uani 1 1 d . . . . .
C14 C 0.4620(3) -0.272(2) 0.1564(5) 0.048(3) Uani 1 1 d . . . . .
H14 H 0.4902 -0.3116 0.1990 0.057 Uiso 1 1 calc R . . . .
C15 C 0.4496(3) -0.404(2) 0.0972(5) 0.047(3) Uani 1 1 d . . . . .
C16 C 0.4090(3) -0.340(2) 0.0323(5) 0.051(3) Uani 1 1 d . . . . .
H16 H 0.4003 -0.4227 -0.0080 0.061 Uiso 1 1 calc R . . . .
C17 C 0.3818(3) -0.146(2) 0.0296(5) 0.049(3) Uani 1 1 d . . . . .
C18 C 0.3922(3) -0.0218(19) 0.0886(5) 0.043(2) Uani 1 1 d . . . . .
C19 C 0.2796(4) 0.248(3) 0.0967(7) 0.088(5) Uani 1 1 d . . . . .
H19A H 0.2889 0.1036 0.1250 0.132 Uiso 1 1 calc GR . . . .
H19B H 0.2644 0.2022 0.0489 0.132 Uiso 1 1 calc GR . . . .
H19C H 0.2582 0.3427 0.1006 0.132 Uiso 1 1 calc GR . . . .
C20 C 0.4704(5) -0.705(3) 0.0461(6) 0.084(5) Uani 1 1 d . . . . .
H20A H 0.4715 -0.5875 0.0168 0.127 Uiso 1 1 calc GR . . . .
H20B H 0.4398 -0.7805 0.0205 0.127 Uiso 1 1 calc GR . . . .
H20C H 0.4941 -0.8283 0.0605 0.127 Uiso 1 1 calc GR . . . .
O1 O 0.3251(3) 0.2337(18) 0.0192(3) 0.072(2) Uani 1 1 d . . . . .
O2 O 0.3612(2) 0.2371(13) 0.1344(3) 0.0448(16) Uani 1 1 d . . . . .
O3 O 0.4212(2) 0.2698(12) 0.4059(3) 0.0449(16) Uani 1 1 d . . . . .
H3A H 0.4163 0.2055 0.4323 0.067 Uiso 1 1 calc GR . . . .
O4 O 0.4446(2) -0.2376(12) 0.4258(3) 0.0385(14) Uani 1 1 d . . . . .
H4 H 0.4415 -0.3841 0.4163 0.058 Uiso 1 1 calc GR . . . .
O5 O 0.5214(2) -0.2514(14) 0.4284(3) 0.0495(17) Uani 1 1 d . . . . .
H5 H 0.5284 -0.2814 0.4673 0.074 Uiso 1 1 calc R . . . .
O6 O 0.4794(2) -0.5828(15) 0.1067(3) 0.060(2) Uani 1 1 d . . . . .
O7 O 0.3430(3) -0.095(2) -0.0359(3) 0.076(3) Uani 1 1 d . . . . .
H7A H 0.3328 0.0407 -0.0362 0.114 Uiso 1 1 calc GR . . . .
C1AA C 0.3615(3) -0.482(2) -0.1839(5) 0.042(2) Uani 1 1 d . . . . .
C3A C 0.3044(3) -0.758(2) -0.1905(5) 0.045(2) Uani 1 1 d . . . . .
H3AA H 0.3309 -0.8653 -0.1574 0.054 Uiso 1 1 calc R . . . .
C4A C 0.2656(3) -0.9082(19) -0.2519(5) 0.045(2) Uani 1 1 d . . . . .
H4AA H 0.2546 -1.0307 -0.2349 0.054 Uiso 1 1 calc R . . . .
H4AB H 0.2787 -0.9937 -0.2727 0.054 Uiso 1 1 calc R . . . .
C5A C 0.2236(3) -0.7545(19) -0.3078(5) 0.042(2) Uani 1 1 d . . . . .
H5AA H 0.2063 -0.6991 -0.2899 0.050 Uiso 1 1 calc R . . . .
H5AB H 0.2354 -0.6103 -0.3169 0.050 Uiso 1 1 calc R . . . .
C6A C 0.1896(3) -0.8886(17) -0.3763(5) 0.038(2) Uani 1 1 d . . . . .
H6AA H 0.1773 -1.0320 -0.3678 0.045 Uiso 1 1 calc R . . . .
H6AB H 0.2066 -0.9441 -0.3947 0.045 Uiso 1 1 calc R . . . .
C7A C 0.1485(3) -0.7271(16) -0.4304(4) 0.033(2) Uani 1 1 d . . . . .
H7AA H 0.1306 -0.6872 -0.4118 0.040 Uiso 1 1 calc R . . . .
C8A C 0.1592(3) -0.4889(16) -0.4499(4) 0.0308(19) Uani 1 1 d . . . . .
H8A H 0.1828 -0.4009 -0.4068 0.037 Uiso 1 1 calc R . . . .
C9A C 0.1766(3) -0.4983(18) -0.4959(4) 0.036(2) Uani 1 1 d . . . . .
H9A H 0.1558 -0.6070 -0.5357 0.044 Uiso 1 1 calc R . . . .
C10A C 0.2278(3) -0.5855(19) -0.4582(4) 0.038(2) Uani 1 1 d . . . . .
H10C H 0.2315 -0.7412 -0.4358 0.046 Uiso 1 1 calc R . . . .
H10D H 0.2340 -0.6127 -0.4926 0.046 Uiso 1 1 calc R . . . .
C11A C 0.2637(3) -0.4092(17) -0.4046(4) 0.031(2) Uani 1 1 d . . . . .
H11A H 0.2578 -0.2426 -0.4143 0.038 Uiso 1 1 calc R . . . .
C12A C 0.3039(3) -0.4748(19) -0.3429(4) 0.036(2) Uani 1 1 d . . . . .
H12A H 0.3080 -0.6378 -0.3289 0.043 Uiso 1 1 calc R . . . .
C13A C 0.3417(3) -0.2965(17) -0.2968(4) 0.032(2) Uani 1 1 d . . . . .
C14A C 0.3520(3) -0.1199(19) -0.3272(4) 0.038(2) Uani 1 1 d . . . . .
H14A H 0.3330 -0.1088 -0.3756 0.046 Uiso 1 1 calc R . . . .
C15A C 0.3896(3) 0.0445(19) -0.2886(5) 0.040(2) Uani 1 1 d . . . . .
C16A C 0.4185(3) 0.028(2) -0.2156(5) 0.046(2) Uani 1 1 d . . . . .
H16A H 0.4441 0.1333 -0.1887 0.056 Uiso 1 1 calc R . . . .
C17A C 0.4082(3) -0.147(2) -0.1845(4) 0.042(2) Uani 1 1 d . . . . .
C18A C 0.3704(3) -0.3136(18) -0.2219(4) 0.037(2) Uani 1 1 d . . . . .
C19A C 0.2884(4) -0.617(3) -0.1530(5) 0.062(3) Uani 1 1 d . . . . .
H19D H 0.2666 -0.4911 -0.1831 0.093 Uiso 1 1 calc GR . . . .
H19E H 0.3153 -0.5444 -0.1115 0.093 Uiso 1 1 calc GR . . . .
H19F H 0.2730 -0.7271 -0.1406 0.093 Uiso 1 1 calc GR . . . .
C20A C 0.4335(3) 0.382(2) -0.2891(5) 0.053(3) Uani 1 1 d . . . . .
H20D H 0.4318 0.4910 -0.3223 0.079 Uiso 1 1 calc GR . . . .
H20E H 0.4635 0.2990 -0.2633 0.079 Uiso 1 1 calc GR . . . .
H20F H 0.4304 0.4744 -0.2575 0.079 Uiso 1 1 calc GR . . . .
O1A O 0.3891(2) -0.5195(15) -0.1203(3) 0.061(2) Uani 1 1 d . . . . .
O2A O 0.3189(2) -0.5890(14) -0.2223(3) 0.0481(17) Uani 1 1 d . . . . .
O3A O 0.1178(2) -0.8725(11) -0.4922(3) 0.0421(16) Uani 1 1 d . . . . .
H3AB H 0.0955 -0.7886 -0.5222 0.063 Uiso 1 1 calc R . . . .
O4A O 0.11479(19) -0.3573(12) -0.4846(3) 0.0404(16) Uani 1 1 d . . . . .
H4AC H 0.1121 -0.2650 -0.5141 0.061 Uiso 1 1 calc R . . . .
O5A O 0.1741(2) -0.2572(14) -0.5216(3) 0.0527(18) Uani 1 1 d . . . . .
H5AC H 0.1583 -0.2604 -0.5643 0.079 Uiso 1 1 calc GR . . . .
O6A O 0.3961(2) 0.2050(14) -0.3252(3) 0.0528(19) Uani 1 1 d . . . . .
O7A O 0.4379(3) -0.1535(19) -0.1126(3) 0.077(3) Uani 1 1 d . . . . .
H7AB H 0.4299 -0.2654 -0.0985 0.116 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 0.0180 0.0090 '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 0.0490 0.0320 '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
O1 C1 C18 122.2(9) . . ?
O1 C1 O2 120.2(8) . . ?
O2 C1 C18 117.5(8) . . ?
C4 C3 H3 108.9 . . ?
C4 C3 C19 113.8(9) . . ?
C19 C3 H3 108.9 . . ?
O2 C3 H3 108.9 . . ?
O2 C3 C4 108.5(7) . . ?
O2 C3 C19 107.7(9) . . ?
C3 C4 H4A 107.5 . . ?
C3 C4 H4B 107.5 . . ?
C3 C4 C5 119.4(10) . . ?
H4A C4 H4B 107.0 . . ?
C5 C4 H4A 107.5 . . ?
C5 C4 H4B 107.5 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.4(8) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.9(8) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C6 C7 H7 107.0 . . ?
C6 C7 C8 113.6(7) . . ?
C8 C7 H7 107.0 . . ?
O3 C7 C6 110.4(8) . . ?
O3 C7 H7 107.0 . . ?
O3 C7 C8 111.6(7) . . ?
C7 C8 H8 108.1 . . ?
C7 C8 C9 117.7(7) . . ?
C9 C8 H8 108.1 . . ?
O4 C8 C7 107.5(6) . . ?
O4 C8 H8 108.1 . . ?
O4 C8 C9 106.9(6) . . ?
C8 C9 H9 108.8 . . ?
C10 C9 C8 116.7(7) . . ?
C10 C9 H9 108.8 . . ?
O5 C9 C8 107.1(7) . . ?
O5 C9 H9 108.8 . . ?
O5 C9 C10 106.3(7) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.2(8) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C10 C11 H11 117.8 . . ?
C12 C11 C10 124.4(10) . . ?
C12 C11 H11 117.8 . . ?
C11 C12 H12 118.2 . . ?
C11 C12 C13 123.7(10) . . ?
C13 C12 H12 118.2 . . ?
C14 C13 C12 118.2(8) . . ?
C14 C13 C18 119.3(9) . . ?
C18 C13 C12 122.3(8) . . ?
C13 C14 H14 118.4 . . ?
C13 C14 C15 123.1(9) . . ?
C15 C14 H14 118.4 . . ?
C16 C15 C14 119.5(9) . . ?
O6 C15 C14 116.9(8) . . ?
O6 C15 C16 123.6(9) . . ?
C15 C16 H16 121.1 . . ?
C15 C16 C17 117.7(9) . . ?
C17 C16 H16 121.1 . . ?
C18 C17 C16 123.6(8) . . ?
O7 C17 C16 113.7(9) . . ?
O7 C17 C18 122.7(9) . . ?
C13 C18 C1 126.2(9) . . ?
C17 C18 C1 117.1(8) . . ?
C17 C18 C13 116.6(9) . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
C1 O2 C3 116.6(7) . . ?
C7 O3 H3A 109.5 . . ?
C8 O4 H4 109.5 . . ?
C9 O5 H5 109.5 . . ?
C15 O6 C20 118.4(8) . . ?
C17 O7 H7A 109.5 . . ?
O1A C1AA C18A 124.2(9) . . ?
O1A C1AA O2A 121.1(9) . . ?
O2A C1AA C18A 114.5(7) . . ?
C4A C3A H3AA 109.7 . . ?
C19A C3A H3AA 109.7 . . ?
C19A C3A C4A 114.0(8) . . ?
O2A C3A H3AA 109.7 . . ?
O2A C3A C4A 103.5(7) . . ?
O2A C3A C19A 110.2(9) . . ?
C3A C4A H4AA 108.9 . . ?
C3A C4A H4AB 108.9 . . ?
C3A C4A C5A 113.4(8) . . ?
H4AA C4A H4AB 107.7 . . ?
C5A C4A H4AA 108.9 . . ?
C5A C4A H4AB 108.9 . . ?
C4A C5A H5AA 108.7 . . ?
C4A C5A H5AB 108.7 . . ?
H5AA C5A H5AB 107.6 . . ?
C6A C5A C4A 114.3(8) . . ?
C6A C5A H5AA 108.7 . . ?
C6A C5A H5AB 108.7 . . ?
C5A C6A H6AA 109.2 . . ?
C5A C6A H6AB 109.2 . . ?
C5A C6A C7A 112.2(8) . . ?
H6AA C6A H6AB 107.9 . . ?
C7A C6A H6AA 109.2 . . ?
C7A C6A H6AB 109.2 . . ?
C6A C7A H7AA 106.8 . . ?
C8A C7A C6A 118.6(7) . . ?
C8A C7A H7AA 106.8 . . ?
O3A C7A C6A 107.8(7) . . ?
O3A C7A H7AA 106.8 . . ?
O3A C7A C8A 109.6(7) . . ?
C7A C8A H8A 108.3 . . ?
C7A C8A C9A 117.8(7) . . ?
C9A C8A H8A 108.3 . . ?
O4A C8A C7A 103.0(6) . . ?
O4A C8A H8A 108.3 . . ?
O4A C8A C9A 110.8(7) . . ?
C8A C9A H9A 108.9 . . ?
C8A C9A C10A 114.5(7) . . ?
C10A C9A H9A 108.9 . . ?
O5A C9A C8A 108.9(8) . . ?
O5A C9A H9A 108.9 . . ?
O5A C9A C10A 106.7(7) . . ?
C9A C10A H10C 108.8 . . ?
C9A C10A H10D 108.8 . . ?
H10C C10A H10D 107.7 . . ?
C11A C10A C9A 113.8(8) . . ?
C11A C10A H10C 108.8 . . ?
C11A C10A H10D 108.8 . . ?
C10A C11A H11A 117.7 . . ?
C12A C11A C10A 124.6(9) . . ?
C12A C11A H11A 117.7 . . ?
C11A C12A H12A 118.8 . . ?
C11A C12A C13A 122.3(9) . . ?
C13A C12A H12A 118.8 . . ?
C14A C13A C12A 118.1(7) . . ?
C14A C13A C18A 119.1(8) . . ?
C18A C13A C12A 122.6(8) . . ?
C13A C14A H14A 118.5 . . ?
C13A C14A C15A 123.0(8) . . ?
C15A C14A H14A 118.5 . . ?
C14A C15A C16A 118.9(9) . . ?
O6A C15A C14A 116.6(8) . . ?
O6A C15A C16A 124.5(8) . . ?
C15A C16A H16A 120.7 . . ?
C17A C16A C15A 118.6(9) . . ?
C17A C16A H16A 120.7 . . ?
C16A C17A C18A 123.8(8) . . ?
O7A C17A C16A 115.8(9) . . ?
O7A C17A C18A 120.4(9) . . ?
C13A C18A C1AA 124.2(8) . . ?
C17A C18A C1AA 119.2(8) . . ?
C17A C18A C13A 116.6(8) . . ?
C3A C19A H19D 109.5 . . ?
C3A C19A H19E 109.5 . . ?
C3A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
O6A C20A H20D 109.5 . . ?
O6A C20A H20E 109.5 . . ?
O6A C20A H20F 109.5 . . ?
C1AA O2A C3A 120.7(7) . . ?
C7A O3A H3AB 109.5 . . ?
C8A O4A H4AC 109.5 . . ?
C9A O5A H5AC 109.5 . . ?
C15A O6A C20A 119.7(7) . . ?
C17A O7A H7AB 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
C1 C18 1.463(13) . ?
C1 O1 1.240(11) . ?
C1 O2 1.334(11) . ?
C3 H3 0.9800 . ?
C3 C4 1.508(15) . ?
C3 C19 1.553(16) . ?
C3 O2 1.468(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.539(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.530(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.511(12) . ?
C7 H7 0.9800 . ?
C7 C8 1.532(12) . ?
C7 O3 1.422(10) . ?
C8 H8 0.9800 . ?
C8 C9 1.534(11) . ?
C8 O4 1.437(9) . ?
C9 H9 0.9800 . ?
C9 C10 1.513(11) . ?
C9 O5 1.441(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.507(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.330(12) . ?
C12 H12 0.9300 . ?
C12 C13 1.490(13) . ?
C13 C14 1.346(14) . ?
C13 C18 1.444(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(14) . ?
C15 C16 1.390(13) . ?
C15 O6 1.345(12) . ?
C16 H16 0.9300 . ?
C16 C17 1.398(15) . ?
C17 C18 1.398(14) . ?
C17 O7 1.359(11) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 O6 1.441(12) . ?
O3 H3A 0.8200 . ?
O4 H4 0.8200 . ?
O5 H5 0.8200 . ?
O7 H7A 0.8200 . ?
C1AA C18A 1.444(13) . ?
C1AA O1A 1.238(11) . ?
C1AA O2A 1.337(11) . ?
C3A H3AA 0.9800 . ?
C3A C4A 1.516(13) . ?
C3A C19A 1.510(15) . ?
C3A O2A 1.460(11) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.525(12) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.520(12) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A C7A 1.521(12) . ?
C7A H7AA 0.9800 . ?
C7A C8A 1.499(13) . ?
C7A O3A 1.440(10) . ?
C8A H8A 0.9800 . ?
C8A C9A 1.531(12) . ?
C8A O4A 1.450(9) . ?
C9A H9A 0.9800 . ?
C9A C10A 1.535(12) . ?
C9A O5A 1.430(12) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C11A 1.495(12) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.350(12) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.478(12) . ?
C13A C14A 1.371(13) . ?
C13A C18A 1.438(12) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.400(12) . ?
C15A C16A 1.400(13) . ?
C15A O6A 1.342(11) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.378(14) . ?
C17A C18A 1.408(13) . ?
C17A O7A 1.378(11) . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C20A O6A 1.436(11) . ?
O3A H3AB 0.8200 . ?
O4A H4AC 0.8200 . ?
O5A H5AC 0.8200 . ?
O7A H7AB 0.8200 . ?
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
C3 C4 C5 C6 74.1(12) . . . . ?
C4 C3 O2 C1 -158.3(9) . . . . ?
C4 C5 C6 C7 -179.1(10) . . . . ?
C5 C6 C7 C8 164.6(8) . . . . ?
C5 C6 C7 O3 -69.2(11) . . . . ?
C6 C7 C8 C9 66.6(10) . . . . ?
C6 C7 C8 O4 -172.7(8) . . . . ?
C7 C8 C9 C10 -69.0(10) . . . . ?
C7 C8 C9 O5 172.1(7) . . . . ?
C8 C9 C10 C11 -48.4(11) . . . . ?
C9 C10 C11 C12 130.9(9) . . . . ?
C10 C11 C12 C13 174.2(7) . . . . ?
C11 C12 C13 C14 -33.6(13) . . . . ?
C11 C12 C13 C18 152.3(9) . . . . ?
C12 C13 C14 C15 -176.8(9) . . . . ?
C12 C13 C18 C1 -9.6(15) . . . . ?
C12 C13 C18 C17 173.1(9) . . . . ?
C13 C14 C15 C16 3.5(16) . . . . ?
C13 C14 C15 O6 -178.5(9) . . . . ?
C14 C13 C18 C1 176.4(10) . . . . ?
C14 C13 C18 C17 -0.9(14) . . . . ?
C14 C15 C16 C17 -0.9(15) . . . . ?
C14 C15 O6 C20 -173.7(11) . . . . ?
C15 C16 C17 C18 -2.6(16) . . . . ?
C15 C16 C17 O7 179.4(10) . . . . ?
C16 C15 O6 C20 4.1(16) . . . . ?
C16 C17 C18 C1 -174.0(10) . . . . ?
C16 C17 C18 C13 3.5(16) . . . . ?
C18 C1 O2 C3 -175.4(9) . . . . ?
C18 C13 C14 C15 -2.6(16) . . . . ?
C19 C3 C4 C5 50.9(13) . . . . ?
C19 C3 O2 C1 78.1(10) . . . . ?
O1 C1 C18 C13 170.3(10) . . . . ?
O1 C1 C18 C17 -12.4(16) . . . . ?
O1 C1 O2 C3 1.7(14) . . . . ?
O2 C1 C18 C13 -12.7(15) . . . . ?
O2 C1 C18 C17 164.6(9) . . . . ?
O2 C3 C4 C5 -68.9(12) . . . . ?
O3 C7 C8 C9 -58.9(9) . . . . ?
O3 C7 C8 O4 61.8(8) . . . . ?
O4 C8 C9 C10 170.0(7) . . . . ?
O4 C8 C9 O5 51.1(8) . . . . ?
O5 C9 C10 C11 71.0(9) . . . . ?
O6 C15 C16 C17 -178.7(10) . . . . ?
O7 C17 C18 C1 3.8(16) . . . . ?
O7 C17 C18 C13 -178.7(10) . . . . ?
C3A C4A C5A C6A 167.1(8) . . . . ?
C4A C3A O2A C1AA -158.4(9) . . . . ?
C4A C5A C6A C7A -179.7(8) . . . . ?
C5A C6A C7A C8A 56.5(10) . . . . ?
C5A C6A C7A O3A -178.3(7) . . . . ?
C6A C7A C8A C9A 73.8(10) . . . . ?
C6A C7A C8A O4A -164.0(7) . . . . ?
C7A C8A C9A C10A -74.0(10) . . . . ?
C7A C8A C9A O5A 166.7(7) . . . . ?
C8A C9A C10A C11A -68.2(10) . . . . ?
C9A C10A C11A C12A 142.8(8) . . . . ?
C10A C11A C12A C13A 169.9(7) . . . . ?
C11A C12A C13A C14A -39.2(12) . . . . ?
C11A C12A C13A C18A 145.9(9) . . . . ?
C12A C13A C14A C15A -174.3(8) . . . . ?
C12A C13A C18A C1AA -8.8(14) . . . . ?
C12A C13A C18A C17A 173.7(8) . . . . ?
C13A C14A C15A C16A 0.3(14) . . . . ?
C13A C14A C15A O6A 178.8(8) . . . . ?
C14A C13A C18A C1AA 176.3(9) . . . . ?
C14A C13A C18A C17A -1.2(12) . . . . ?
C14A C15A C16A C17A -1.1(14) . . . . ?
C14A C15A O6A C20A 179.0(9) . . . . ?
C15A C16A C17A C18A 0.8(15) . . . . ?
C15A C16A C17A O7A 179.9(9) . . . . ?
C16A C15A O6A C20A -2.7(14) . . . . ?
C16A C17A C18A C1AA -177.2(9) . . . . ?
C16A C17A C18A C13A 0.4(14) . . . . ?
C18A C1AA O2A C3A -178.1(8) . . . . ?
C18A C13A C14A C15A 0.8(13) . . . . ?
C19A C3A C4A C5A 59.1(12) . . . . ?
C19A C3A O2A C1AA 79.4(11) . . . . ?
O1A C1AA C18A C13A 170.4(9) . . . . ?
O1A C1AA C18A C17A -12.2(15) . . . . ?
O1A C1AA O2A C3A -1.6(15) . . . . ?
O2A C1AA C18A C13A -13.2(14) . . . . ?
O2A C1AA C18A C17A 164.2(8) . . . . ?
O2A C3A C4A C5A -60.6(10) . . . . ?
O3A C7A C8A C9A -50.5(9) . . . . ?
O3A C7A C8A O4A 71.7(7) . . . . ?
O4A C8A C9A C10A 167.9(7) . . . . ?
O4A C8A C9A O5A 48.5(9) . . . . ?
O5A C9A C10A C11A 52.3(9) . . . . ?
O6A C15A C16A C17A -179.5(9) . . . . ?
O7A C17A C18A C1AA 3.6(14) . . . . ?
O7A C17A C18A C13A -178.8(9) . . . . ?
