#------------------------------------------------------------------------------
#$Date: 2024-12-16 19:33:52 +0200 (Mon, 16 Dec 2024) $
#$Revision: 296876 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158463.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_7158463
loop_
_publ_author_name
'Peng, Xiaogang'
'Zhou, Shuang'
'Liu, Junjun'
'Gao, Ying'
'Chang, Jinling'
'Ruan, Hanli'
_publ_section_title
;
 (+-)-Usphenethylones A-C, three pairs of heterodimeric polyketide
 enantiomers from Aspergillus ustus 3.3904.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              694
_journal_page_last               700
_journal_paper_doi               10.1039/d1ob02006d
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H22 O8'
_chemical_formula_sum            'C21 H22 O8'
_chemical_formula_weight         402.38
_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
_audit_creation_date             2021-04-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.5505(2)
_cell_length_b                   17.1723(8)
_cell_length_c                   48.042(2)
_cell_measurement_reflns_used    8326
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      46.40
_cell_measurement_theta_min      2.38
_cell_volume                     3754.1(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            18403
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        46.474
_diffrn_reflns_theta_max         46.474
_diffrn_reflns_theta_min         1.600
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.7492
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         4878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0394
_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)+(0.0521P)²+0.3244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4303
_reflns_number_total             4878
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02006d2.cif
_cod_data_source_block           210323f_0m
_cod_depositor_comments
;
Adding full bibliography for 7158459--7158466.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H44 O16'
_cod_original_formula_weight         804.77
_cod_original_formula_moiety         '2(C21 H22 O8)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3754.2(3)
_cod_database_code               7158463
_shelx_shelxl_version_number     2018/3
_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   0.944
_shelx_estimated_absorpt_t_min   0.891
_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:
 C8(H8), C9(H9), C10(H10), C8A(H8A), C9A(H9A), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C11A(H11C,H11D), C18A(H18C,H18D)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C5A(H5A), C7A(H7A)
2.d Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C2'(H2'A,H2'B,H2'C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,H2BC), C17A(H17D,H17E,H17F),
 C19A(H19D,H19E,H19F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1A(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
C1 C -0.1520(9) 0.4637(2) 0.56634(8) 0.0274(10) Uani 1 1 d . . . . .
C1' C -0.6086(10) 0.6365(2) 0.57689(8) 0.0318(10) Uani 1 1 d . . . . .
H1'A H -0.753534 0.625266 0.562344 0.048 Uiso 1 1 calc R U . . .
H1'B H -0.481026 0.679200 0.570812 0.048 Uiso 1 1 calc R U . . .
H1'C H -0.710478 0.651547 0.594041 0.048 Uiso 1 1 calc R U . . .
C2 C -0.0001(9) 0.4253(2) 0.54484(8) 0.0259(9) Uani 1 1 d . . . . .
C2' C 0.1620(11) 0.2907(2) 0.47133(8) 0.0342(11) Uani 1 1 d . . . . .
H2'A H 0.192714 0.314121 0.452959 0.051 Uiso 1 1 calc R U . . .
H2'B H 0.048644 0.242508 0.469335 0.051 Uiso 1 1 calc R U . . .
H2'C H 0.352697 0.278984 0.479834 0.051 Uiso 1 1 calc R U . . .
C3 C 0.0040(9) 0.4545(2) 0.51773(8) 0.0240(9) Uani 1 1 d . . . . .
C4 C -0.1421(9) 0.5239(2) 0.51233(8) 0.0242(9) Uani 1 1 d . . . . .
C5 C -0.2912(9) 0.5644(2) 0.53346(8) 0.0247(9) Uani 1 1 d . . . . .
H5 H -0.387563 0.612174 0.529457 0.030 Uiso 1 1 calc R U . . .
C6 C -0.2966(9) 0.5343(2) 0.56004(8) 0.0264(10) Uani 1 1 d . . . . .
C7 C -0.1630(11) 0.4317(2) 0.59400(8) 0.0361(11) Uani 1 1 d . . . . .
H7 H -0.276069 0.458469 0.607598 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1688(9) 0.4108(2) 0.49554(8) 0.0259(9) Uani 1 1 d . . . . .
H8 H 0.363529 0.394128 0.503124 0.031 Uiso 1 1 calc R U . . .
C9 C -0.1312(9) 0.5587(2) 0.48337(7) 0.0228(9) Uani 1 1 d . . . . .
H9 H -0.330566 0.579254 0.478569 0.027 Uiso 1 1 calc R U . . .
C10 C -0.0529(9) 0.4952(2) 0.46316(7) 0.0246(9) Uani 1 1 d . . . . .
H10 H -0.213069 0.455309 0.463285 0.030 Uiso 1 1 calc R U . . .
C11 C 0.0910(9) 0.6264(2) 0.48220(7) 0.0253(10) Uani 1 1 d . . . . .
H11A H -0.005607 0.674839 0.488586 0.030 Uiso 1 1 calc R U . . .
H11B H 0.256555 0.615216 0.494953 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2068(9) 0.6380(2) 0.45336(8) 0.0231(9) Uani 1 1 d . . . . .
C13 C 0.3926(9) 0.7034(2) 0.44824(8) 0.0277(10) Uani 1 1 d . . . . .
C14 C 0.4216(9) 0.6632(2) 0.39960(8) 0.0272(10) Uani 1 1 d . . . . .
C15 C 0.2504(9) 0.6008(2) 0.40407(8) 0.0249(10) Uani 1 1 d . . . . .
C16 C 0.1507(9) 0.5884(2) 0.43209(8) 0.0240(9) Uani 1 1 d . . . . .
C17 C 0.1549(10) 0.5449(2) 0.38163(8) 0.0320(10) Uani 1 1 d . . . . .
H17A H 0.235072 0.561765 0.363691 0.048 Uiso 1 1 calc R U . . .
H17B H -0.060221 0.543987 0.380630 0.048 Uiso 1 1 calc R U . . .
H17C H 0.227585 0.492576 0.385995 0.048 Uiso 1 1 calc R U . . .
C18 C 0.5616(10) 0.6901(2) 0.37325(8) 0.0311(10) Uani 1 1 d . . . . .
H18A H 0.559481 0.646816 0.359632 0.037 Uiso 1 1 calc R U . . .
H18B H 0.769404 0.703514 0.377017 0.037 Uiso 1 1 calc R U . . .
C19 C 0.4089(10) 0.7605(2) 0.36046(8) 0.0361(11) Uani 1 1 d . . . . .
H19A H 0.519584 0.778111 0.344134 0.054 Uiso 1 1 calc R U . . .
H19B H 0.399634 0.802587 0.374200 0.054 Uiso 1 1 calc R U . . .
H19C H 0.209261 0.746026 0.354817 0.054 Uiso 1 1 calc R U . . .
O1 O -0.0338(8) 0.37109(17) 0.60124(6) 0.0430(8) Uani 1 1 d . . . . .
O2 O 0.1469(7) 0.35832(15) 0.55003(6) 0.0338(7) Uani 1 1 d . . . . .
H2 H 0.131900 0.347103 0.566984 0.051 Uiso 1 1 calc R U . . .
O3 O -0.4343(6) 0.56838(15) 0.58198(5) 0.0324(7) Uani 1 1 d . . . . .
O4 O 0.0033(6) 0.34434(14) 0.48877(5) 0.0291(7) Uani 1 1 d . . . . .
O5 O 0.2156(6) 0.45864(14) 0.47139(5) 0.0264(7) Uani 1 1 d . . . . .
O6 O -0.0112(6) 0.52146(14) 0.43538(5) 0.0257(6) Uani 1 1 d . . . . .
O7 O 0.4955(6) 0.71302(15) 0.42102(5) 0.0284(7) Uani 1 1 d . . . . .
O8 O 0.4737(7) 0.75129(16) 0.46504(5) 0.0344(7) Uani 1 1 d . . . . .
C1A C 0.3520(9) 0.4774(2) 0.18627(8) 0.0297(10) Uani 1 1 d . . . . .
C1B C 0.8454(10) 0.6142(2) 0.22109(8) 0.0339(11) Uani 1 1 d . . . . .
H1BA H 0.966359 0.655404 0.212880 0.051 Uiso 1 1 calc R U . . .
H1BB H 0.972796 0.575245 0.229860 0.051 Uiso 1 1 calc R U . . .
H1BC H 0.714317 0.636695 0.235128 0.051 Uiso 1 1 calc R U . . .
C2A C 0.1792(9) 0.4127(2) 0.19336(8) 0.0301(10) Uani 1 1 d . . . . .
C2B C -0.0733(11) 0.1843(2) 0.21167(9) 0.0423(12) Uani 1 1 d . . . . .
H2BA H -0.220340 0.199767 0.197832 0.063 Uiso 1 1 calc R U . . .
H2BB H -0.172080 0.169897 0.229052 0.063 Uiso 1 1 calc R U . . .
H2BC H 0.038534 0.139653 0.204664 0.063 Uiso 1 1 calc R U . . .
C3A C 0.1666(9) 0.3845(2) 0.22081(8) 0.0266(10) Uani 1 1 d . . . . .
C4A C 0.3252(9) 0.4234(2) 0.24108(8) 0.0240(9) Uani 1 1 d . . . . .
C5A C 0.4938(9) 0.4893(2) 0.23483(8) 0.0266(9) Uani 1 1 d . . . . .
H5A H 0.595885 0.516184 0.249164 0.032 Uiso 1 1 calc R U . . .
C6A C 0.5103(9) 0.5149(2) 0.20765(8) 0.0272(10) Uani 1 1 d . . . . .
C7A C 0.3662(11) 0.5049(3) 0.15778(9) 0.0390(12) Uani 1 1 d . . . . .
H7A H 0.490990 0.547683 0.153565 0.047 Uiso 1 1 calc R U . . .
C8A C -0.0195(10) 0.3146(2) 0.22722(8) 0.0290(10) Uani 1 1 d . . . . .
H8A H -0.212727 0.320347 0.217520 0.035 Uiso 1 1 calc R U . . .
C9A C 0.1950(9) 0.3150(2) 0.27200(8) 0.0277(10) Uani 1 1 d . . . . .
H9A H 0.347743 0.280665 0.263419 0.033 Uiso 1 1 calc R U . . .
C10A C 0.3004(9) 0.3984(2) 0.27107(8) 0.0259(9) Uani 1 1 d . . . . .
H10A H 0.500387 0.400769 0.279649 0.031 Uiso 1 1 calc R U . . .
C11A C 0.0981(9) 0.4533(2) 0.28719(8) 0.0267(10) Uani 1 1 d . . . . .
H11C H 0.213299 0.498515 0.293819 0.032 Uiso 1 1 calc R U . . .
H11D H -0.056814 0.472911 0.274544 0.032 Uiso 1 1 calc R U . . .
C12A C -0.0428(9) 0.4142(2) 0.31153(7) 0.0246(9) Uani 1 1 d . . . . .
C13A C -0.2295(9) 0.4599(2) 0.32890(8) 0.0268(10) Uani 1 1 d . . . . .
C14A C -0.3132(10) 0.3446(2) 0.35708(8) 0.0298(10) Uani 1 1 d . . . . .
C15A C -0.1506(10) 0.2997(2) 0.34031(8) 0.0276(10) Uani 1 1 d . . . . .
C16A C -0.0189(9) 0.3367(2) 0.31660(8) 0.0262(10) Uani 1 1 d . . . . .
C17A C -0.1060(11) 0.2134(2) 0.34498(9) 0.0384(12) Uani 1 1 d . . . . .
H17D H -0.176896 0.199330 0.363572 0.058 Uiso 1 1 calc R U . . .
H17E H 0.103569 0.200992 0.343483 0.058 Uiso 1 1 calc R U . . .
H17F H -0.215815 0.184076 0.330918 0.058 Uiso 1 1 calc R U . . .
C18A C -0.4665(10) 0.3226(2) 0.38341(8) 0.0322(10) Uani 1 1 d . . . . .
H18C H -0.520836 0.266809 0.382596 0.039 Uiso 1 1 calc R U . . .
H18D H -0.649876 0.353235 0.385090 0.039 Uiso 1 1 calc R U . . .
C19A C -0.2776(13) 0.3366(4) 0.40885(9) 0.0732(19) Uani 1 1 d . . . . .
H19D H -0.094089 0.307167 0.407128 0.110 Uiso 1 1 calc R U . . .
H19E H -0.383497 0.319541 0.425530 0.110 Uiso 1 1 calc R U . . .
H19F H -0.232963 0.392304 0.410369 0.110 Uiso 1 1 calc R U . . .
O1A O 0.0159(7) 0.37580(16) 0.17410(6) 0.0366(7) Uani 1 1 d . . . . .
H1A H 0.049109 0.395150 0.158351 0.055 Uiso 1 1 calc R U . . .
O2A O 0.2221(8) 0.47495(18) 0.13870(6) 0.0508(9) Uani 1 1 d . . . . .
O3A O 0.6739(6) 0.57783(15) 0.19976(5) 0.0336(7) Uani 1 1 d . . . . .
O4A O 0.1239(7) 0.24847(16) 0.21678(5) 0.0349(7) Uani 1 1 d . . . . .
O5A O -0.0713(6) 0.30763(15) 0.25665(5) 0.0291(7) Uani 1 1 d . . . . .
O6A O 0.1330(6) 0.28784(14) 0.29941(5) 0.0298(7) Uani 1 1 d . . . . .
O7A O -0.3538(6) 0.42281(14) 0.35177(5) 0.0286(7) Uani 1 1 d . . . . .
O8A O -0.2969(6) 0.52767(15) 0.32527(5) 0.0318(7) Uani 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 0.0137 0.0067 '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 0.0389 0.0241 '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
C2 C1 C6 118.3(3) . . ?
C2 C1 C7 121.0(4) . . ?
C6 C1 C7 120.7(4) . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O3 C1' H1'A 109.5 . . ?
O3 C1' H1'B 109.5 . . ?
O3 C1' H1'C 109.5 . . ?
C3 C2 C1 121.5(3) . . ?
O2 C2 C1 120.4(3) . . ?
O2 C2 C3 118.1(3) . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
O4 C2' H2'A 109.5 . . ?
O4 C2' H2'B 109.5 . . ?
O4 C2' H2'C 109.5 . . ?
C2 C3 C8 119.3(3) . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 C8 122.3(3) . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 C9 119.7(3) . . ?
C5 C4 C9 119.0(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.8(4) . . ?
O3 C6 C1 114.7(3) . . ?
O3 C6 C5 124.4(3) . . ?
C1 C7 H7 117.9 . . ?
O1 C7 C1 124.1(4) . . ?
O1 C7 H7 117.9 . . ?
C3 C8 H8 109.1 . . ?
O4 C8 C3 107.6(3) . . ?
O4 C8 H8 109.1 . . ?
O4 C8 O5 110.9(3) . . ?
O5 C8 C3 111.2(3) . . ?
O5 C8 H8 109.1 . . ?
C4 C9 H9 108.7 . . ?
C4 C9 C11 110.6(3) . . ?
C10 C9 C4 108.3(3) . . ?
C10 C9 H9 108.7 . . ?
C10 C9 C11 111.6(3) . . ?
C11 C9 H9 108.7 . . ?
C9 C10 H10 108.7 . . ?
O5 C10 C9 110.0(3) . . ?
O5 C10 H10 108.7 . . ?
O6 C10 C9 114.1(3) . . ?
O6 C10 H10 108.7 . . ?
O6 C10 O5 106.5(3) . . ?
C9 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C9 111.5(3) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 118.3(3) . . ?
C16 C12 C11 123.2(3) . . ?
C16 C12 C13 118.5(3) . . ?
O7 C13 C12 116.9(3) . . ?
O8 C13 C12 126.9(4) . . ?
O8 C13 O7 116.2(4) . . ?
C15 C14 C18 129.1(4) . . ?
C15 C14 O7 121.1(3) . . ?
O7 C14 C18 109.8(3) . . ?
C14 C15 C16 116.8(3) . . ?
C14 C15 C17 124.2(4) . . ?
C16 C15 C17 119.0(4) . . ?
C12 C16 C15 123.6(4) . . ?
C12 C16 O6 122.7(3) . . ?
O6 C16 C15 113.6(3) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.0 . . ?
C14 C18 H18B 109.0 . . ?
C14 C18 C19 113.1(3) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 O2 H2 109.5 . . ?
C6 O3 C1' 118.3(3) . . ?
C8 O4 C2' 112.7(3) . . ?
C10 O5 C8 110.3(3) . . ?
C16 O6 C10 116.4(3) . . ?
C14 O7 C13 122.9(3) . . ?
C2A C1A C6A 118.1(4) . . ?
C2A C1A C7A 120.8(4) . . ?
C6A C1A C7A 121.1(4) . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O3A C1B H1BA 109.5 . . ?
O3A C1B H1BB 109.5 . . ?
O3A C1B H1BC 109.5 . . ?
C1A C2A C3A 121.6(4) . . ?
O1A C2A C1A 121.0(4) . . ?
O1A C2A C3A 117.4(4) . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
O4A C2B H2BA 109.5 . . ?
O4A C2B H2BB 109.5 . . ?
O4A C2B H2BC 109.5 . . ?
C2A C3A C8A 119.4(4) . . ?
C4A C3A C2A 118.2(4) . . ?
C4A C3A C8A 122.4(3) . . ?
C3A C4A C5A 121.7(3) . . ?
C3A C4A C10A 119.8(3) . . ?
C5A C4A C10A 118.4(3) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A C4A 119.3(4) . . ?
C6A C5A H5A 120.3 . . ?
C5A C6A C1A 121.1(4) . . ?
O3A C6A C1A 115.9(3) . . ?
O3A C6A C5A 123.0(4) . . ?
C1A C7A H7A 118.7 . . ?
O2A C7A C1A 122.7(4) . . ?
O2A C7A H7A 118.7 . . ?
C3A C8A H8A 108.8 . . ?
O4A C8A C3A 108.2(3) . . ?
O4A C8A H8A 108.8 . . ?
O4A C8A O5A 111.1(3) . . ?
O5A C8A C3A 111.1(3) . . ?
O5A C8A H8A 108.8 . . ?
C10A C9A H9A 109.0 . . ?
O5A C9A H9A 109.0 . . ?
O5A C9A C10A 109.8(3) . . ?
O5A C9A O6A 106.3(3) . . ?
O6A C9A H9A 109.0 . . ?
O6A C9A C10A 113.6(3) . . ?
C4A C10A C9A 108.7(3) . . ?
C4A C10A H10A 108.3 . . ?
C4A C10A C11A 110.8(3) . . ?
C9A C10A H10A 108.3 . . ?
C9A C10A C11A 112.2(3) . . ?
C11A C10A H10A 108.3 . . ?
C10A C11A H11C 109.1 . . ?
C10A C11A H11D 109.1 . . ?
H11C C11A H11D 107.9 . . ?
C12A C11A C10A 112.3(3) . . ?
C12A C11A H11C 109.1 . . ?
C12A C11A H11D 109.1 . . ?
C13A C12A C11A 117.9(3) . . ?
C16A C12A C11A 123.1(4) . . ?
C16A C12A C13A 118.8(4) . . ?
O7A C13A C12A 117.0(3) . . ?
O8A C13A C12A 126.3(4) . . ?
O8A C13A O7A 116.7(3) . . ?
C15A C14A C18A 128.5(4) . . ?
C15A C14A O7A 121.6(4) . . ?
O7A C14A C18A 109.9(3) . . ?
C14A C15A C16A 117.0(3) . . ?
C14A C15A C17A 123.3(4) . . ?
C16A C15A C17A 119.7(4) . . ?
C12A C16A C15A 122.9(4) . . ?
C12A C16A O6A 122.3(3) . . ?
O6A C16A C15A 114.8(3) . . ?
C15A C17A H17D 109.5 . . ?
C15A C17A H17E 109.5 . . ?
C15A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C14A C18A H18C 109.2 . . ?
C14A C18A H18D 109.2 . . ?
C14A C18A C19A 112.2(4) . . ?
H18C C18A H18D 107.9 . . ?
C19A C18A H18C 109.2 . . ?
C19A C18A H18D 109.2 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C2A O1A H1A 109.5 . . ?
C6A O3A C1B 116.3(3) . . ?
C8A O4A C2B 113.0(3) . . ?
C9A O5A C8A 111.2(3) . . ?
C16A O6A C9A 117.3(3) . . ?
C14A O7A C13A 122.5(3) . . ?
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 C2 1.407(5) . ?
C1 C6 1.411(5) . ?
C1 C7 1.439(5) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C1' O3 1.434(5) . ?
C2 C3 1.395(5) . ?
C2 O2 1.354(4) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C2' O4 1.439(4) . ?
C3 C4 1.389(5) . ?
C3 C8 1.504(5) . ?
C4 C5 1.405(5) . ?
C4 C9 1.515(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(5) . ?
C6 O3 1.359(5) . ?
C7 H7 0.9500 . ?
C7 O1 1.245(5) . ?
C8 H8 1.0000 . ?
C8 O4 1.406(5) . ?
C8 O5 1.438(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.504(5) . ?
C9 C11 1.541(5) . ?
C10 H10 1.0000 . ?
C10 O5 1.429(5) . ?
C10 O6 1.422(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.496(5) . ?
C12 C13 1.427(6) . ?
C12 C16 1.355(5) . ?
C13 O7 1.398(5) . ?
C13 O8 1.209(5) . ?
C14 C15 1.343(6) . ?
C14 C18 1.490(5) . ?
C14 O7 1.379(5) . ?
C15 C16 1.436(5) . ?
C15 C17 1.507(5) . ?
C16 O6 1.374(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.524(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 H2 0.8400 . ?
C1A C2A 1.403(6) . ?
C1A C6A 1.410(6) . ?
C1A C7A 1.449(6) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C1B O3A 1.431(5) . ?
C2A C3A 1.406(5) . ?
C2A O1A 1.346(5) . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C2B H2BC 0.9800 . ?
C2B O4A 1.442(5) . ?
C3A C4A 1.383(5) . ?
C3A C8A 1.501(5) . ?
C4A C5A 1.401(5) . ?
C4A C10A 1.507(5) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.380(5) . ?
C6A O3A 1.366(5) . ?
C7A H7A 0.9500 . ?
C7A O2A 1.239(5) . ?
C8A H8A 1.0000 . ?
C8A O4A 1.403(5) . ?
C8A O5A 1.438(5) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.512(5) . ?
C9A O5A 1.424(5) . ?
C9A O6A 1.425(5) . ?
C10A H10A 1.0000 . ?
C10A C11A 1.528(5) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C12A 1.493(5) . ?
C12A C13A 1.426(5) . ?
C12A C16A 1.358(5) . ?
C13A O7A 1.390(5) . ?
C13A O8A 1.216(5) . ?
C14A C15A 1.338(6) . ?
C14A C18A 1.493(6) . ?
C14A O7A 1.379(5) . ?
C15A C16A 1.435(5) . ?
C15A C17A 1.512(5) . ?
C16A O6A 1.365(5) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.513(6) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
O1A H1A 0.8400 . ?
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
O2 H2 O1 0.84 1.86 2.604(4) 147.3 . yes
O1A H1A O2A 0.84 1.84 2.583(4) 146.4 . 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 1.2(6) . . . . ?
C1 C2 C3 C8 -179.7(4) . . . . ?
C1 C6 O3 C1' -174.5(4) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C1 C6 O3 -179.1(4) . . . . ?
C2 C1 C7 O1 3.0(7) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 C9 177.5(4) . . . . ?
C2 C3 C8 O4 73.9(5) . . . . ?
C2 C3 C8 O5 -164.5(3) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C3 C4 C9 C10 20.9(5) . . . . ?
C3 C4 C9 C11 -101.7(4) . . . . ?
C3 C8 O4 C2' -169.7(3) . . . . ?
C3 C8 O5 C10 -48.9(4) . . . . ?
C4 C3 C8 O4 -107.0(4) . . . . ?
C4 C3 C8 O5 14.5(5) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C4 C5 C6 O3 -179.9(4) . . . . ?
C4 C9 C10 O5 -55.4(4) . . . . ?
C4 C9 C10 O6 -175.0(3) . . . . ?
C4 C9 C11 C12 154.5(3) . . . . ?
C5 C4 C9 C10 -161.5(3) . . . . ?
C5 C4 C9 C11 75.9(4) . . . . ?
C5 C6 O3 C1' 6.0(6) . . . . ?
C6 C1 C2 C3 -1.4(6) . . . . ?
C6 C1 C2 O2 178.6(4) . . . . ?
C6 C1 C7 O1 -177.8(4) . . . . ?
C7 C1 C2 C3 177.9(4) . . . . ?
C7 C1 C2 O2 -2.1(6) . . . . ?
C7 C1 C6 C5 -178.8(4) . . . . ?
C7 C1 C6 O3 1.7(6) . . . . ?
C8 C3 C4 C5 -179.1(4) . . . . ?
C8 C3 C4 C9 -1.5(6) . . . . ?
C9 C4 C5 C6 -178.4(4) . . . . ?
C9 C10 O5 C8 72.8(4) . . . . ?
C9 C10 O6 C16 44.1(4) . . . . ?
C9 C11 C12 C13 173.8(3) . . . . ?
C9 C11 C12 C16 -8.1(5) . . . . ?
C10 C9 C11 C12 33.8(4) . . . . ?
C11 C9 C10 O5 66.7(4) . . . . ?
C11 C9 C10 O6 -53.0(4) . . . . ?
C11 C12 C13 O7 -179.5(3) . . . . ?
C11 C12 C13 O8 1.3(6) . . . . ?
C11 C12 C16 C15 177.3(4) . . . . ?
C11 C12 C16 O6 -2.0(6) . . . . ?
C12 C13 O7 C14 0.9(5) . . . . ?
C12 C16 O6 C10 -16.2(5) . . . . ?
C13 C12 C16 C15 -4.7(6) . . . . ?
C13 C12 C16 O6 176.1(3) . . . . ?
C14 C15 C16 C12 3.7(6) . . . . ?
C14 C15 C16 O6 -177.0(3) . . . . ?
C15 C14 C18 C19 105.1(5) . . . . ?
C15 C14 O7 C13 -1.8(6) . . . . ?
C15 C16 O6 C10 164.5(3) . . . . ?
C16 C12 C13 O7 2.3(5) . . . . ?
C16 C12 C13 O8 -176.9(4) . . . . ?
C17 C15 C16 C12 -175.2(4) . . . . ?
C17 C15 C16 O6 4.0(5) . . . . ?
C18 C14 C15 C16 178.7(4) . . . . ?
C18 C14 C15 C17 -2.4(7) . . . . ?
C18 C14 O7 C13 179.0(3) . . . . ?
O2 C2 C3 C4 -178.9(3) . . . . ?
O2 C2 C3 C8 0.2(6) . . . . ?
O4 C8 O5 C10 70.7(4) . . . . ?
O5 C8 O4 C2' 68.5(4) . . . . ?
O5 C10 O6 C16 -77.5(4) . . . . ?
O6 C10 O5 C8 -163.1(3) . . . . ?
O7 C14 C15 C16 -0.4(6) . . . . ?
O7 C14 C15 C17 178.5(4) . . . . ?
O7 C14 C18 C19 -75.8(4) . . . . ?
O8 C13 O7 C14 -179.9(4) . . . . ?
C1A C2A C3A C4A 1.4(6) . . . . ?
C1A C2A C3A C8A -179.4(4) . . . . ?
C1A C6A O3A C1B -177.4(3) . . . . ?
C2A C1A C6A C5A -0.7(6) . . . . ?
C2A C1A C6A O3A -179.6(3) . . . . ?
C2A C1A C7A O2A 2.3(6) . . . . ?
C2A C3A C4A C5A 0.3(6) . . . . ?
C2A C3A C4A C10A 175.7(3) . . . . ?
C2A C3A C8A O4A 74.0(4) . . . . ?
C2A C3A C8A O5A -163.8(3) . . . . ?
C3A C4A C5A C6A -2.1(6) . . . . ?
C3A C4A C10A C9A 22.1(5) . . . . ?
C3A C4A C10A C11A -101.6(4) . . . . ?
C3A C8A O4A C2B -157.1(3) . . . . ?
C3A C8A O5A C9A -48.6(4) . . . . ?
C4A C3A C8A O4A -106.8(4) . . . . ?
C4A C3A C8A O5A 15.4(5) . . . . ?
C4A C5A C6A C1A 2.3(6) . . . . ?
C4A C5A C6A O3A -178.8(3) . . . . ?
C4A C10A C11A C12A 153.5(3) . . . . ?
C5A C4A C10A C9A -162.3(4) . . . . ?
C5A C4A C10A C11A 73.9(4) . . . . ?
C5A C6A O3A C1B 3.7(5) . . . . ?
C6A C1A C2A C3A -1.2(6) . . . . ?
C6A C1A C2A O1A 178.0(4) . . . . ?
C6A C1A C7A O2A -177.5(4) . . . . ?
C7A C1A C2A C3A 179.0(4) . . . . ?
C7A C1A C2A O1A -1.8(6) . . . . ?
C7A C1A C6A C5A 179.2(4) . . . . ?
C7A C1A C6A O3A 0.2(6) . . . . ?
C8A C3A C4A C5A -178.9(4) . . . . ?
C8A C3A C4A C10A -3.5(6) . . . . ?
C9A C10A C11A C12A 31.7(5) . . . . ?
C10A C4A C5A C6A -177.5(4) . . . . ?
C10A C9A O5A C8A 71.2(4) . . . . ?
C10A C9A O6A C16A 43.8(5) . . . . ?
C10A C11A C12A C13A 177.9(3) . . . . ?
C10A C11A C12A C16A -7.1(6) . . . . ?
C11A C12A C13A O7A -178.7(3) . . . . ?
C11A C12A C13A O8A 3.3(6) . . . . ?
C11A C12A C16A C15A 178.9(4) . . . . ?
C11A C12A C16A O6A -1.2(6) . . . . ?
C12A C13A O7A C14A -3.1(5) . . . . ?
C12A C16A O6A C9A -17.7(5) . . . . ?
C13A C12A C16A C15A -6.2(6) . . . . ?
C13A C12A C16A O6A 173.7(3) . . . . ?
C14A C15A C16A C12A 3.0(6) . . . . ?
C14A C15A C16A O6A -177.0(3) . . . . ?
C15A C14A C18A C19A 92.2(6) . . . . ?
C15A C14A O7A C13A -0.1(6) . . . . ?
C15A C16A O6A C9A 162.3(3) . . . . ?
C16A C12A C13A O7A 6.1(5) . . . . ?
C16A C12A C13A O8A -171.9(4) . . . . ?
C17A C15A C16A C12A -178.1(4) . . . . ?
C17A C15A C16A O6A 1.9(6) . . . . ?
C18A C14A C15A C16A -177.9(4) . . . . ?
C18A C14A C15A C17A 3.2(7) . . . . ?
C18A C14A O7A C13A 178.4(3) . . . . ?
O1A C2A C3A C4A -177.8(3) . . . . ?
O1A C2A C3A C8A 1.4(5) . . . . ?
O4A C8A O5A C9A 72.0(4) . . . . ?
O5A C8A O4A C2B 80.7(4) . . . . ?
O5A C9A C10A C4A -54.7(4) . . . . ?
O5A C9A C10A C11A 68.2(4) . . . . ?
O5A C9A O6A C16A -77.0(4) . . . . ?
O6A C9A C10A C4A -173.6(3) . . . . ?
O6A C9A C10A C11A -50.7(5) . . . . ?
O6A C9A O5A C8A -165.6(3) . . . . ?
O7A C14A C15A C16A 0.3(6) . . . . ?
O7A C14A C15A C17A -178.6(4) . . . . ?
O7A C14A C18A C19A -86.1(5) . . . . ?
O8A C13A O7A C14A 175.1(4) . . . . ?
