#------------------------------------------------------------------------------
#$Date: 2024-07-11 04:51:18 +0300 (Thu, 11 Jul 2024) $
#$Revision: 293368 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312550.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312550
loop_
_publ_author_name
'Asmaey, Mostafa A.'
'Kalofolias, Dimitris A.'
'Charavgi, Maria Despoina'
'Abdel-Rahim, Ismail R'
'Chrysina, Evangelia D.'
'Abatis, Dennis'
_publ_section_title
;
 Crystal structure of the cytotoxic macrocyclic trichothecene Isororidin
 A.
;
_journal_coeditor_code           UX3006
_journal_issue                   8
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624006144
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C29 H40 O9'
_chemical_formula_moiety         'C29 H40 O9'
_chemical_formula_sum            'C29 H40 O9'
_chemical_formula_weight         532.61
_chemical_name_common
;
Isororidin A
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2707(4)
_cell_length_b                   15.2236(6)
_cell_length_c                   20.0806(8)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.91
_cell_measurement_theta_min      4.4
_cell_volume                     2834.0(2)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_collection
;
APEX2 (Bruker, 2021)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            101717
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.097
_diffrn_reflns_theta_min         3.643
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.220
_refine_ls_abs_structure_details
;
Flack x determined using 2264 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0407
_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)+(0.0618P)²+1.0952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                5338
_reflns_number_total             5548
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ux3006.cif
_cod_data_source_block           I
_cod_database_code               2312550
_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_min   0.943
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.88908(18) 0.27189(12) 0.51273(8) 0.0240(4) Uani d 1 . .
O O2 0.9025(2) 0.38349(12) 0.67471(9) 0.0272(4) Uani d 1 . .
O O3 0.55743(19) 0.51939(11) 0.47181(9) 0.0247(4) Uani d 1 . .
O O4 0.1743(2) 0.69785(13) 0.64506(9) 0.0308(4) Uani d 1 . .
O O5 0.55825(19) 0.34501(11) 0.66449(8) 0.0220(4) Uani d 1 . .
O O6 0.3838(2) 0.49608(15) 0.39552(11) 0.0424(5) Uani d 1 . .
O O7 0.2988(2) 0.66973(14) 0.40501(10) 0.0397(5) Uani d 1 . .
H H7 0.337967 0.671580 0.367303 0.060 Uiso calc 1 . .
O O8 -0.0389(2) 0.80771(13) 0.70903(10) 0.0361(5) Uani d 1 . .
H H8 0.003475 0.841615 0.735599 0.054 Uiso calc 1 . .
O O9 0.37443(19) 0.41830(12) 0.61579(9) 0.0269(4) Uani d 1 . .
C C2 0.8665(3) 0.27417(17) 0.58343(12) 0.0239(5) Uani d 1 . .
H H2 0.941895 0.239374 0.607361 0.029 Uiso calc 1 . .
C C3 0.7140(3) 0.24545(15) 0.60435(12) 0.0237(5) Uani d 1 . .
H H3A 0.714192 0.222712 0.650543 0.028 Uiso calc 1 . .
H H3B 0.677134 0.199050 0.574293 0.028 Uiso calc 1 . .
C C4 0.6207(3) 0.32912(15) 0.59909(11) 0.0198(5) Uani d 1 . .
H H4 0.543332 0.321485 0.564896 0.024 Uiso calc 1 . .
C C5 0.7257(2) 0.40513(16) 0.57878(12) 0.0189(5) Uani d 1 . .
C C6 0.7370(3) 0.40627(15) 0.50005(11) 0.0194(5) Uani d 1 . .
C C7 0.8563(3) 0.46869(17) 0.47578(13) 0.0255(5) Uani d 1 . .
H H7A 0.835163 0.528884 0.491673 0.031 Uiso calc 1 . .
H H7B 0.949524 0.450303 0.495403 0.031 Uiso calc 1 . .
C C8 0.8701(3) 0.46984(18) 0.39997(13) 0.0301(6) Uani d 1 . .
H H8A 0.790742 0.505592 0.381129 0.036 Uiso calc 1 . .
H H8B 0.962284 0.498322 0.387684 0.036 Uiso calc 1 . .
C C9 0.8652(3) 0.37965(19) 0.36967(12) 0.0280(6) Uani d 1 . .
C C10 0.8205(3) 0.31031(17) 0.40345(12) 0.0250(5) Uani d 1 . .
H H10 0.818015 0.255442 0.380946 0.030 Uiso calc 1 . .
C C11 0.7731(3) 0.31230(16) 0.47532(11) 0.0209(5) Uani d 1 . .
H H11 0.684913 0.275005 0.480016 0.025 Uiso calc 1 . .
C C12 0.8689(3) 0.36850(17) 0.60468(12) 0.0226(5) Uani d 1 . .
C C13 0.9983(3) 0.4175(2) 0.62296(13) 0.0289(6) Uani d 1 . .
H H13A 0.998626 0.481667 0.614993 0.035 Uiso calc 1 . .
H H13B 1.092774 0.388245 0.616854 0.035 Uiso calc 1 . .
C C14 0.6885(3) 0.49472(15) 0.60854(13) 0.0228(5) Uani d 1 . .
H H14A 0.758586 0.538439 0.593183 0.034 Uiso calc 1 . .
H H14B 0.691533 0.491081 0.657245 0.034 Uiso calc 1 . .
H H14C 0.591501 0.512065 0.594273 0.034 Uiso calc 1 . .
C C15 0.5923(3) 0.42707(16) 0.46636(12) 0.0221(5) Uani d 1 . .
H H15A 0.597356 0.410455 0.418753 0.027 Uiso calc 1 . .
H H15B 0.515051 0.391867 0.487463 0.027 Uiso calc 1 . .
C C16 0.9125(3) 0.3731(2) 0.29815(14) 0.0380(7) Uani d 1 . .
H H16A 1.014581 0.389273 0.294656 0.057 Uiso calc 1 . .
H H16B 0.854565 0.413067 0.270815 0.057 Uiso calc 1 . .
H H16C 0.899321 0.312700 0.282417 0.057 Uiso calc 1 . .
C C1' 0.4428(3) 0.54367(19) 0.43490(13) 0.0296(6) Uani d 1 . .
C C2' 0.3983(3) 0.63724(18) 0.45204(13) 0.0287(6) Uani d 1 . .
H H2' 0.485817 0.675635 0.452173 0.034 Uiso calc 1 . .
C C3' 0.3294(3) 0.63843(18) 0.52177(14) 0.0291(6) Uani d 1 . .
H H3' 0.395944 0.606240 0.552451 0.035 Uiso calc 1 . .
C C4' 0.3149(4) 0.7322(2) 0.54813(16) 0.0407(7) Uani d 1 . .
H H4'A 0.399591 0.766598 0.533323 0.049 Uiso calc 1 . .
H H4'B 0.228023 0.759272 0.528101 0.049 Uiso calc 1 . .
C C5' 0.3034(4) 0.7386(2) 0.62343(17) 0.0407(7) Uani d 1 . .
H H5'A 0.387367 0.709419 0.644329 0.049 Uiso calc 1 . .
H H5'B 0.303563 0.801101 0.637090 0.049 Uiso calc 1 . .
C C6' 0.1495(3) 0.69731(18) 0.71470(13) 0.0274(5) Uani d 1 . .
H H6' 0.209471 0.744725 0.735249 0.033 Uiso calc 1 . .
C C7' 0.1896(3) 0.61153(17) 0.74684(13) 0.0277(5) Uani d 1 . .
H H7' 0.166965 0.605138 0.792725 0.033 Uiso calc 1 . .
C C8' 0.2536(3) 0.54364(17) 0.71731(13) 0.0265(5) Uani d 1 . .
H H8' 0.270664 0.545400 0.670677 0.032 Uiso calc 1 . .
C C9' 0.2979(3) 0.46714(17) 0.75504(13) 0.0281(5) Uani d 1 . .
H H9' 0.264277 0.463987 0.799677 0.034 Uiso calc 1 . .
C C10' 0.3807(3) 0.40016(17) 0.73433(12) 0.0267(5) Uani d 1 . .
H H10' 0.406954 0.356344 0.765766 0.032 Uiso calc 1 . .
C C11' 0.4333(3) 0.39102(15) 0.66526(12) 0.0231(5) Uani d 1 . .
C C12' 0.1877(3) 0.5878(2) 0.51995(15) 0.0372(6) Uani d 1 . .
H H12A 0.122060 0.615490 0.487947 0.056 Uiso calc 1 . .
H H12B 0.143561 0.588379 0.564304 0.056 Uiso calc 1 . .
H H12C 0.206171 0.526987 0.506428 0.056 Uiso calc 1 . .
C C13' -0.0095(3) 0.71915(18) 0.72682(13) 0.0298(6) Uani d 1 . .
H H13' -0.031032 0.711192 0.775237 0.036 Uiso calc 1 . .
C C14' -0.1081(3) 0.65997(19) 0.68701(15) 0.0334(6) Uani d 1 . .
H H14D -0.208572 0.677363 0.694432 0.050 Uiso calc 1 . .
H H14E -0.094561 0.598944 0.701241 0.050 Uiso calc 1 . .
H H14F -0.085000 0.665237 0.639549 0.050 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C11 . . 113.23(17) ?
C12 O2 C13 . . 59.98(16) ?
C1' O3 C15 . . 113.7(2) ?
C5' O4 C6' . . 116.2(2) ?
C11' O5 C4 . . 115.90(18) ?
C2' O7 H7 . . 109.5 ?
C13' O8 H8 . . 109.5 ?
O1 C2 C12 . . 107.62(19) ?
O1 C2 C3 . . 113.4(2) ?
C12 C2 C3 . . 102.03(19) ?
O1 C2 H2 . . 111.1 ?
C12 C2 H2 . . 111.1 ?
C3 C2 H2 . . 111.1 ?
C2 C3 C4 . . 105.16(19) ?
C2 C3 H3A . . 110.7 ?
C4 C3 H3A . . 110.7 ?
C2 C3 H3B . . 110.7 ?
C4 C3 H3B . . 110.7 ?
H3A C3 H3B . . 108.8 ?
O5 C4 C3 . . 107.36(18) ?
O5 C4 C5 . . 111.07(18) ?
C3 C4 C5 . . 106.24(19) ?
O5 C4 H4 . . 110.7 ?
C3 C4 H4 . . 110.7 ?
C5 C4 H4 . . 110.7 ?
C14 C5 C12 . . 112.8(2) ?
C14 C5 C4 . . 114.66(19) ?
C12 C5 C4 . . 100.44(19) ?
C14 C5 C6 . . 113.28(19) ?
C12 C5 C6 . . 106.61(18) ?
C4 C5 C6 . . 107.99(18) ?
C15 C6 C7 . . 111.19(19) ?
C15 C6 C11 . . 103.77(18) ?
C7 C6 C11 . . 108.23(19) ?
C15 C6 C5 . . 112.62(19) ?
C7 C6 C5 . . 111.73(19) ?
C11 C6 C5 . . 108.88(18) ?
C8 C7 C6 . . 112.5(2) ?
C8 C7 H7A . . 109.1 ?
C6 C7 H7A . . 109.1 ?
C8 C7 H7B . . 109.1 ?
C6 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C7 . . 113.0(2) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C8 . . 122.1(2) ?
C10 C9 C16 . . 121.9(3) ?
C8 C9 C16 . . 116.0(2) ?
C9 C10 C11 . . 124.5(2) ?
C9 C10 H10 . . 117.8 ?
C11 C10 H10 . . 117.8 ?
O1 C11 C10 . . 105.75(18) ?
O1 C11 C6 . . 112.71(18) ?
C10 C11 C6 . . 112.8(2) ?
O1 C11 H11 . . 108.5 ?
C10 C11 H11 . . 108.5 ?
C6 C11 H11 . . 108.5 ?
O2 C12 C13 . . 60.13(16) ?
O2 C12 C2 . . 115.3(2) ?
C13 C12 C2 . . 125.0(2) ?
O2 C12 C5 . . 117.1(2) ?
C13 C12 C5 . . 127.7(2) ?
C2 C12 C5 . . 103.9(2) ?
C12 C13 O2 . . 59.90(15) ?
C12 C13 H13A . . 117.8 ?
O2 C13 H13A . . 117.8 ?
C12 C13 H13B . . 117.8 ?
O2 C13 H13B . . 117.8 ?
H13A C13 H13B . . 114.9 ?
C5 C14 H14A . . 109.5 ?
C5 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C5 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O3 C15 C6 . . 111.26(19) ?
O3 C15 H15A . . 109.4 ?
C6 C15 H15A . . 109.4 ?
O3 C15 H15B . . 109.4 ?
C6 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
C9 C16 H16A . . 109.5 ?
C9 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C9 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O6 C1' O3 . . 123.7(3) ?
O6 C1' C2' . . 126.0(3) ?
O3 C1' C2' . . 110.3(2) ?
O7 C2' C1' . . 110.7(2) ?
O7 C2' C3' . . 109.5(2) ?
C1' C2' C3' . . 109.2(2) ?
O7 C2' H2' . . 109.1 ?
C1' C2' H2' . . 109.1 ?
C3' C2' H2' . . 109.1 ?
C12' C3' C4' . . 113.9(2) ?
C12' C3' C2' . . 109.3(2) ?
C4' C3' C2' . . 111.3(2) ?
C12' C3' H3' . . 107.4 ?
C4' C3' H3' . . 107.4 ?
C2' C3' H3' . . 107.4 ?
C5' C4' C3' . . 114.3(2) ?
C5' C4' H4'A . . 108.7 ?
C3' C4' H4'A . . 108.7 ?
C5' C4' H4'B . . 108.7 ?
C3' C4' H4'B . . 108.7 ?
H4'A C4' H4'B . . 107.6 ?
O4 C5' C4' . . 109.7(3) ?
O4 C5' H5'A . . 109.7 ?
C4' C5' H5'A . . 109.7 ?
O4 C5' H5'B . . 109.7 ?
C4' C5' H5'B . . 109.7 ?
H5'A C5' H5'B . . 108.2 ?
O4 C6' C7' . . 112.9(2) ?
O4 C6' C13' . . 108.2(2) ?
C7' C6' C13' . . 111.0(2) ?
O4 C6' H6' . . 108.2 ?
C7' C6' H6' . . 108.2 ?
C13' C6' H6' . . 108.2 ?
C8' C7' C6' . . 126.4(3) ?
C8' C7' H7' . . 116.8 ?
C6' C7' H7' . . 116.8 ?
C7' C8' C9' . . 121.2(2) ?
C7' C8' H8' . . 119.4 ?
C9' C8' H8' . . 119.4 ?
C10' C9' C8' . . 127.6(2) ?
C10' C9' H9' . . 116.2 ?
C8' C9' H9' . . 116.2 ?
C9' C10' C11' . . 123.5(2) ?
C9' C10' H10' . . 118.3 ?
C11' C10' H10' . . 118.3 ?
O9 C11' O5 . . 123.7(2) ?
O9 C11' C10' . . 126.3(2) ?
O5 C11' C10' . . 110.0(2) ?
C3' C12' H12A . . 109.5 ?
C3' C12' H12B . . 109.5 ?
H12A C12' H12B . . 109.5 ?
C3' C12' H12C . . 109.5 ?
H12A C12' H12C . . 109.5 ?
H12B C12' H12C . . 109.5 ?
O8 C13' C14' . . 108.4(2) ?
O8 C13' C6' . . 110.6(2) ?
C14' C13' C6' . . 111.6(2) ?
O8 C13' H13' . . 108.7 ?
C14' C13' H13' . . 108.7 ?
C6' C13' H13' . . 108.7 ?
C13' C14' H14D . . 109.5 ?
C13' C14' H14E . . 109.5 ?
H14D C14' H14E . . 109.5 ?
C13' C14' H14F . . 109.5 ?
H14D C14' H14F . . 109.5 ?
H14E C14' H14F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.436(3) ?
O1 C11 . 1.449(3) ?
O2 C12 . 1.458(3) ?
O2 C13 . 1.462(3) ?
O3 C1' . 1.347(3) ?
O3 C15 . 1.446(3) ?
O4 C5' . 1.416(4) ?
O4 C6' . 1.417(3) ?
O5 C11' . 1.354(3) ?
O5 C4 . 1.456(3) ?
O6 C1' . 1.204(4) ?
O7 C2' . 1.409(3) ?
O7 H7 . 0.8400 ?
O8 C13' . 1.421(3) ?
O8 H8 . 0.8400 ?
O9 C11' . 1.207(3) ?
C2 C12 . 1.498(4) ?
C2 C3 . 1.538(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.543(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.566(3) ?
C4 H4 . 1.0000 ?
C5 C14 . 1.528(3) ?
C5 C12 . 1.531(3) ?
C5 C6 . 1.584(3) ?
C6 C15 . 1.535(3) ?
C6 C7 . 1.538(3) ?
C6 C11 . 1.551(3) ?
C7 C8 . 1.528(4) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.502(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.321(4) ?
C9 C16 . 1.505(4) ?
C10 C11 . 1.509(3) ?
C10 H10 . 0.9500 ?
C11 H11 . 1.0000 ?
C12 C13 . 1.460(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C1' C2' . 1.523(4) ?
C2' C3' . 1.539(4) ?
C2' H2' . 1.0000 ?
C3' C12' . 1.524(4) ?
C3' C4' . 1.528(4) ?
C3' H3' . 1.0000 ?
C4' C5' . 1.519(4) ?
C4' H4'A . 0.9900 ?
C4' H4'B . 0.9900 ?
C5' H5'A . 0.9900 ?
C5' H5'B . 0.9900 ?
C6' C7' . 1.503(4) ?
C6' C13' . 1.530(4) ?
C6' H6' . 1.0000 ?
C7' C8' . 1.331(4) ?
C7' H7' . 0.9500 ?
C8' C9' . 1.449(4) ?
C8' H8' . 0.9500 ?
C9' C10' . 1.343(4) ?
C9' H9' . 0.9500 ?
C10' C11' . 1.477(3) ?
C10' H10' . 0.9500 ?
C12' H12A . 0.9800 ?
C12' H12B . 0.9800 ?
C12' H12C . 0.9800 ?
C13' C14' . 1.512(4) ?
C13' H13' . 1.0000 ?
C14' H14D . 0.9800 ?
C14' H14E . 0.9800 ?
C14' H14F . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O7 H7 O8 4_566 0.84 1.94 2.761(3) 166.7 yes
O8 H8 O2 3_656 0.84 2.10 2.895(3) 157.7 yes
C4 H4 O1 4_456 1.00 2.55 3.467(3) 152.6 yes
C13 H13B O9 1_655 0.99 2.65 3.490(3) 142.6 yes
C7' H7' O6 2_565 0.95 2.62 3.473(3) 149.8 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 O1 C2 C12 . . . . -65.2(2) ?
C11 O1 C2 C3 . . . . 46.9(3) ?
O1 C2 C3 C4 . . . . -85.5(2) ?
C12 C2 C3 C4 . . . . 30.0(2) ?
C11' O5 C4 C3 . . . . -154.6(2) ?
C11' O5 C4 C5 . . . . 89.7(2) ?
C2 C3 C4 O5 . . . . -121.9(2) ?
C2 C3 C4 C5 . . . . -3.0(2) ?
O5 C4 C5 C14 . . . . -29.1(3) ?
C3 C4 C5 C14 . . . . -145.6(2) ?
O5 C4 C5 C12 . . . . 92.1(2) ?
C3 C4 C5 C12 . . . . -24.3(2) ?
O5 C4 C5 C6 . . . . -156.44(18) ?
C3 C4 C5 C6 . . . . 87.1(2) ?
C14 C5 C6 C15 . . . . -64.8(3) ?
C12 C5 C6 C15 . . . . 170.5(2) ?
C4 C5 C6 C15 . . . . 63.3(2) ?
C14 C5 C6 C7 . . . . 61.2(3) ?
C12 C5 C6 C7 . . . . -63.5(2) ?
C4 C5 C6 C7 . . . . -170.71(19) ?
C14 C5 C6 C11 . . . . -179.32(19) ?
C12 C5 C6 C11 . . . . 56.0(2) ?
C4 C5 C6 C11 . . . . -51.2(2) ?
C15 C6 C7 C8 . . . . -53.9(3) ?
C11 C6 C7 C8 . . . . 59.4(3) ?
C5 C6 C7 C8 . . . . 179.3(2) ?
C6 C7 C8 C9 . . . . -44.4(3) ?
C7 C8 C9 C10 . . . . 14.6(4) ?
C7 C8 C9 C16 . . . . -166.1(2) ?
C8 C9 C10 C11 . . . . -1.4(4) ?
C16 C9 C10 C11 . . . . 179.3(2) ?
C2 O1 C11 C10 . . . . 175.6(2) ?
C2 O1 C11 C6 . . . . 51.9(3) ?
C9 C10 C11 O1 . . . . -106.0(3) ?
C9 C10 C11 C6 . . . . 17.6(3) ?
C15 C6 C11 O1 . . . . -166.89(18) ?
C7 C6 C11 O1 . . . . 74.9(2) ?
C5 C6 C11 O1 . . . . -46.7(2) ?
C15 C6 C11 C10 . . . . 73.4(2) ?
C7 C6 C11 C10 . . . . -44.8(3) ?
C5 C6 C11 C10 . . . . -166.4(2) ?
C13 O2 C12 C2 . . . . 117.4(3) ?
C13 O2 C12 C5 . . . . -119.9(3) ?
O1 C2 C12 O2 . . . . -157.67(19) ?
C3 C2 C12 O2 . . . . 82.7(2) ?
O1 C2 C12 C13 . . . . -87.6(3) ?
C3 C2 C12 C13 . . . . 152.8(2) ?
O1 C2 C12 C5 . . . . 72.8(2) ?
C3 C2 C12 C5 . . . . -46.8(2) ?
C14 C5 C12 O2 . . . . 38.1(3) ?
C4 C5 C12 O2 . . . . -84.4(2) ?
C6 C5 C12 O2 . . . . 163.10(19) ?
C14 C5 C12 C13 . . . . -33.7(3) ?
C4 C5 C12 C13 . . . . -156.3(2) ?
C6 C5 C12 C13 . . . . 91.2(3) ?
C14 C5 C12 C2 . . . . 166.5(2) ?
C4 C5 C12 C2 . . . . 44.0(2) ?
C6 C5 C12 C2 . . . . -68.5(2) ?
C2 C12 C13 O2 . . . . -101.5(3) ?
C5 C12 C13 O2 . . . . 102.7(3) ?
C1' O3 C15 C6 . . . . 170.8(2) ?
C7 C6 C15 O3 . . . . -51.0(3) ?
C11 C6 C15 O3 . . . . -167.16(18) ?
C5 C6 C15 O3 . . . . 75.3(2) ?
C15 O3 C1' O6 . . . . -7.6(4) ?
C15 O3 C1' C2' . . . . 170.7(2) ?
O6 C1' C2' O7 . . . . -13.8(4) ?
O3 C1' C2' O7 . . . . 168.0(2) ?
O6 C1' C2' C3' . . . . 106.9(3) ?
O3 C1' C2' C3' . . . . -71.3(3) ?
O7 C2' C3' C12' . . . . 54.8(3) ?
C1' C2' C3' C12' . . . . -66.6(3) ?
O7 C2' C3' C4' . . . . -71.8(3) ?
C1' C2' C3' C4' . . . . 166.8(3) ?
C12' C3' C4' C5' . . . . 78.2(4) ?
C2' C3' C4' C5' . . . . -157.8(3) ?
C6' O4 C5' C4' . . . . 179.0(2) ?
C3' C4' C5' O4 . . . . -64.7(4) ?
C5' O4 C6' C7' . . . . -99.2(3) ?
C5' O4 C6' C13' . . . . 137.6(2) ?
O4 C6' C7' C8' . . . . 5.8(4) ?
C13' C6' C7' C8' . . . . 127.4(3) ?
C6' C7' C8' C9' . . . . 174.7(2) ?
C7' C8' C9' C10' . . . . -169.7(3) ?
C8' C9' C10' C11' . . . . -4.7(4) ?
C4 O5 C11' O9 . . . . -0.1(3) ?
C4 O5 C11' C10' . . . . 178.57(19) ?
C9' C10' C11' O9 . . . . -28.5(4) ?
C9' C10' C11' O5 . . . . 152.8(2) ?
O4 C6' C13' O8 . . . . -68.1(3) ?
C7' C6' C13' O8 . . . . 167.6(2) ?
O4 C6' C13' C14' . . . . 52.7(3) ?
C7' C6' C13' C14' . . . . -71.6(3) ?
