#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/35/2223532.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_2223532
loop_
_publ_author_name
'Fronczek, Chris F.'
'Gomez-Barrios, Marco L.'
'Fischer, Nikolaus H.'
'Fronczek, Frank R.'
_publ_section_title
;
 11β,13-Dihydrolactucin-8-O-acetate hemihydrate
;
_journal_coeditor_code           PV2210
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2564
_journal_page_last               o2565
_journal_paper_doi               10.1107/S160053680903829X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H20 O6, 0.5H2 O'
_chemical_formula_moiety         'C17 H20 O6, 0.5(H2 O)'
_chemical_formula_sum            'C17 H21 O6.5'
_chemical_formula_weight         329.34
_chemical_name_common
;
11β,13-Dihydrolactucin-8-O-acetate hemihydrate
;
_chemical_name_systematic
;
9-hydroxymethyl-3,6-dimethyl-2,7-dioxo-
3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl
acetate hemihydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 100.850(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9276(5)
_cell_length_b                   7.4658(5)
_cell_length_c                   19.8571(10)
_cell_measurement_reflns_used    9656
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      2.27
_cell_volume                     1591.05(15)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23565
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         69.04
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  0.9168
_exptl_absorpt_correction_T_min  0.7962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.138
_refine_ls_abs_structure_details 'Flack (1983), 2516 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_coef       0.00101(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         5642
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0314P)²+0.4082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0677
_reflns_number_gt                5513
_reflns_number_total             5642
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2210.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C17 H21 O6.50'
_cod_database_code               2223532
_cod_database_fobs_code          2223532
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.36074(9) 0.72760(16) 0.04034(5) 0.0256(2) Uani d . 1 . .
O O2 0.54683(12) 0.8177(2) 0.02323(6) 0.0473(4) Uani d . 1 . .
O O3 -0.15403(9) 0.63628(15) 0.05240(5) 0.0255(2) Uani d . 1 . .
O O4 0.19069(10) 0.67077(15) -0.19419(5) 0.0240(2) Uani d . 1 . .
O O5 0.07993(12) 0.91019(18) -0.23883(6) 0.0345(3) Uani d . 1 . .
O O6 0.25725(10) 0.54254(16) 0.22516(5) 0.0252(2) Uani d . 1 . .
H H6O 0.2544(19) 0.651(3) 0.2400(10) 0.038 Uiso d . 1 . .
C C1 0.02479(13) 0.5810(2) -0.00331(8) 0.0203(3) Uani d . 1 . .
C C2 -0.04236(14) 0.61236(19) 0.05490(7) 0.0211(3) Uani d . 1 . .
C C3 0.05145(14) 0.6056(2) 0.11802(7) 0.0216(3) Uani d . 1 . .
H H3 0.0338 0.6189 0.1628 0.026 Uiso calc R 1 . .
C C4 0.16502(14) 0.5782(2) 0.10450(7) 0.0196(3) Uani d . 1 . .
C C5 0.16294(13) 0.5614(2) 0.02770(7) 0.0191(3) Uani d . 1 . .
H H5 0.1933 0.4402 0.0170 0.023 Uiso calc R 1 . .
C C6 0.23650(13) 0.7063(2) -0.00135(6) 0.0201(3) Uani d . 1 . .
H H6 0.1907 0.8225 -0.0025 0.024 Uiso calc R 1 . .
C C7 0.26251(13) 0.6665(2) -0.07304(7) 0.0210(3) Uani d . 1 . .
H H7 0.2901 0.5390 -0.0742 0.025 Uiso calc R 1 . .
C C8 0.14873(13) 0.6930(2) -0.12911(6) 0.0210(3) Uani d . 1 . .
H H8 0.1133 0.8156 -0.1260 0.025 Uiso calc R 1 . .
C C9 0.04910(14) 0.5504(2) -0.12638(7) 0.0221(3) Uani d . 1 . .
H H9A -0.0085 0.5477 -0.1713 0.026 Uiso calc R 1 . .
H H9B 0.0903 0.4319 -0.1195 0.026 Uiso calc R 1 . .
C C10 -0.02665(14) 0.5780(2) -0.07062(7) 0.0210(3) Uani d . 1 . .
C C11 0.37468(16) 0.7875(3) -0.07459(8) 0.0334(4) Uani d . 1 . .
H H11 0.3446 0.9122 -0.0861 0.040 Uiso calc R 1 . .
C C12 0.44090(16) 0.7817(3) -0.00012(8) 0.0327(4) Uani d . 1 . .
C C13 0.46307(17) 0.7337(4) -0.12182(9) 0.0504(6) Uani d . 1 . .
H H13A 0.5417 0.7993 -0.1089 0.076 Uiso calc R 1 . .
H H13B 0.4252 0.7625 -0.1693 0.076 Uiso calc R 1 . .
H H13C 0.4793 0.6047 -0.1177 0.076 Uiso calc R 1 . .
C C14 -0.16387(14) 0.5988(2) -0.09751(8) 0.0238(3) Uani d . 1 . .
H H14A -0.2067 0.6226 -0.0593 0.036 Uiso calc R 1 . .
H H14B -0.1967 0.4884 -0.1209 0.036 Uiso calc R 1 . .
H H14C -0.1778 0.6990 -0.1299 0.036 Uiso calc R 1 . .
C C15 0.28150(14) 0.5536(2) 0.15730(7) 0.0232(3) Uani d . 1 . .
H H15A 0.3241 0.4427 0.1469 0.028 Uiso calc R 1 . .
H H15B 0.3384 0.6554 0.1546 0.028 Uiso calc R 1 . .
C C16 0.14984(13) 0.7902(2) -0.24440(7) 0.0212(3) Uani d . 1 . .
C C17 0.20561(16) 0.7550(2) -0.30617(7) 0.0298(4) Uani d . 1 . .
H H17A 0.1449 0.7846 -0.3476 0.045 Uiso calc R 1 . .
H H17B 0.2283 0.6282 -0.3073 0.045 Uiso calc R 1 . .
H H17C 0.2803 0.8290 -0.3042 0.045 Uiso calc R 1 . .
O O1A 0.10059(9) 0.30940(15) 0.46612(5) 0.0229(2) Uani d . 1 . .
O O2A -0.08856(10) 0.34776(18) 0.49033(5) 0.0320(3) Uani d . 1 . .
O O3A 0.61587(9) 0.19216(15) 0.43180(5) 0.0258(2) Uani d . 1 . .
O O4A 0.29523(9) 0.22296(15) 0.69401(5) 0.0214(2) Uani d . 1 . .
O O5A 0.45039(11) 0.39546(17) 0.74928(5) 0.0320(3) Uani d . 1 . .
O O6A 0.18713(10) 0.21622(16) 0.27100(5) 0.0258(2) Uani d . 1 . .
H H60A 0.2039(19) 0.317(3) 0.2552(10) 0.039 Uiso d . 1 . .
C C1A 0.44199(13) 0.17797(19) 0.49391(7) 0.0188(3) Uani d . 1 . .
C C2A 0.50439(13) 0.1995(2) 0.43344(7) 0.0205(3) Uani d . 1 . .
C C3A 0.40492(14) 0.2229(2) 0.37344(7) 0.0215(3) Uani d . 1 . .
H H3A 0.4187 0.2443 0.3283 0.026 Uiso calc R 1 . .
C C4A 0.29305(13) 0.2106(2) 0.39010(7) 0.0199(3) Uani d . 1 . .
C C5A 0.30176(13) 0.1693(2) 0.46618(7) 0.0190(3) Uani d . 1 . .
H H5A 0.2720 0.0442 0.4712 0.023 Uiso calc R 1 . .
C C6A 0.22888(13) 0.2972(2) 0.50361(7) 0.0191(3) Uani d . 1 . .
H H6A 0.2685 0.4184 0.5069 0.023 Uiso calc R 1 . .
C C7A 0.21326(12) 0.2344(2) 0.57504(6) 0.0196(3) Uani d . 1 . .
H H7A 0.1957 0.1028 0.5728 0.024 Uiso calc R 1 . .
C C8A 0.33015(13) 0.2662(2) 0.62853(7) 0.0194(3) Uani d . 1 . .
H H8A 0.3582 0.3935 0.6277 0.023 Uiso calc R 1 . .
C C9A 0.43475(14) 0.1374(2) 0.61948(7) 0.0215(3) Uani d . 1 . .
H H91A 0.4979 0.1383 0.6624 0.026 Uiso calc R 1 . .
H H92A 0.3995 0.0150 0.6138 0.026 Uiso calc R 1 . .
C C10A 0.50089(13) 0.17411(19) 0.56004(7) 0.0193(3) Uani d . 1 . .
C C11A 0.09343(13) 0.3330(2) 0.58339(7) 0.0250(3) Uani d . 1 . .
H H11A 0.1154 0.4596 0.5969 0.030 Uiso calc R 1 . .
C C12A 0.02146(14) 0.3323(2) 0.51022(7) 0.0243(3) Uani d . 1 . .
C C13A 0.01788(14) 0.2562(3) 0.63306(8) 0.0307(4) Uani d . 1 . .
H H13D -0.0645 0.3130 0.6254 0.046 Uiso calc R 1 . .
H H13E 0.0609 0.2793 0.6802 0.046 Uiso calc R 1 . .
H H13F 0.0083 0.1268 0.6257 0.046 Uiso calc R 1 . .
C C14A 0.63888(13) 0.2030(2) 0.58228(7) 0.0230(3) Uani d . 1 . .
H H14D 0.6761 0.2265 0.5420 0.034 Uiso calc R 1 . .
H H14E 0.6768 0.0957 0.6059 0.034 Uiso calc R 1 . .
H H14F 0.6535 0.3057 0.6135 0.034 Uiso calc R 1 . .
C C15A 0.17124(13) 0.2246(2) 0.34040(7) 0.0231(3) Uani d . 1 . .
H H15C 0.1158 0.1259 0.3492 0.028 Uiso calc R 1 . .
H H15D 0.1303 0.3391 0.3481 0.028 Uiso calc R 1 . .
C C16A 0.36493(14) 0.2941(2) 0.75074(7) 0.0233(3) Uani d . 1 . .
C C17A 0.32219(17) 0.2309(3) 0.81365(8) 0.0351(4) Uani d . 1 . .
H H17D 0.3798 0.2738 0.8543 0.053 Uiso calc R 1 . .
H H17E 0.3202 0.0996 0.8140 0.053 Uiso calc R 1 . .
H H17F 0.2385 0.2776 0.8140 0.053 Uiso calc R 1 . .
O O7 0.29309(12) 0.89082(18) 0.25390(6) 0.0333(3) Uani d . 1 . .
H H72 0.371(2) 0.911(3) 0.2489(11) 0.050(6) Uiso d . 1 . .
H H71 0.259(3) 0.997(4) 0.2573(14) 0.077(9) Uiso d . 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
C12 O1 C6 . . 109.37(11) ?
C16 O4 C8 . . 117.62(11) ?
C15 O6 H6O . . 107.0(14) ?
C10 C1 C2 . . 126.38(13) ?
C10 C1 C5 . . 126.46(13) ?
C2 C1 C5 . . 107.11(12) ?
O3 C2 C3 . . 124.87(13) ?
O3 C2 C1 . . 128.30(13) ?
C3 C2 C1 . . 106.82(12) ?
C4 C3 C2 . . 111.18(13) ?
C4 C3 H3 . . 124.4 ?
C2 C3 H3 . . 124.4 ?
C3 C4 C15 . . 125.26(13) ?
C3 C4 C5 . . 111.98(13) ?
C15 C4 C5 . . 122.64(13) ?
C6 C5 C4 . . 114.20(12) ?
C6 C5 C1 . . 109.34(11) ?
C4 C5 C1 . . 102.88(11) ?
C6 C5 H5 . . 110.1 ?
C4 C5 H5 . . 110.1 ?
C1 C5 H5 . . 110.1 ?
O1 C6 C5 . . 111.28(11) ?
O1 C6 C7 . . 103.45(11) ?
C5 C6 C7 . . 114.66(12) ?
O1 C6 H6 . . 109.1 ?
C5 C6 H6 . . 109.1 ?
C7 C6 H6 . . 109.1 ?
C8 C7 C11 . . 117.26(12) ?
C8 C7 C6 . . 112.75(12) ?
C11 C7 C6 . . 101.19(12) ?
C8 C7 H7 . . 108.4 ?
C11 C7 H7 . . 108.4 ?
C6 C7 H7 . . 108.4 ?
O4 C8 C7 . . 106.51(11) ?
O4 C8 C9 . . 107.23(11) ?
C7 C8 C9 . . 111.92(12) ?
O4 C8 H8 . . 110.4 ?
C7 C8 H8 . . 110.4 ?
C9 C8 H8 . . 110.4 ?
C10 C9 C8 . . 114.89(12) ?
C10 C9 H9A . . 108.5 ?
C8 C9 H9A . . 108.5 ?
C10 C9 H9B . . 108.5 ?
C8 C9 H9B . . 108.5 ?
H9A C9 H9B . . 107.5 ?
C1 C10 C14 . . 123.54(14) ?
C1 C10 C9 . . 122.87(13) ?
C14 C10 C9 . . 113.58(12) ?
C12 C11 C13 . . 110.55(15) ?
C12 C11 C7 . . 101.57(12) ?
C13 C11 C7 . . 117.49(16) ?
C12 C11 H11 . . 108.9 ?
C13 C11 H11 . . 108.9 ?
C7 C11 H11 . . 108.9 ?
O2 C12 O1 . . 121.59(14) ?
O2 C12 C11 . . 128.38(15) ?
O1 C12 C11 . . 110.02(13) ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O6 C15 C4 . . 112.58(12) ?
O6 C15 H15A . . 109.1 ?
C4 C15 H15A . . 109.1 ?
O6 C15 H15B . . 109.1 ?
C4 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.8 ?
O5 C16 O4 . . 123.69(13) ?
O5 C16 C17 . . 125.11(14) ?
O4 C16 C17 . . 111.18(13) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C12A O1A C6A . . 110.30(10) ?
C16A O4A C8A . . 117.23(11) ?
C15A O6A H60A . . 113.1(14) ?
C10A C1A C2A . . 125.23(13) ?
C10A C1A C5A . . 127.71(13) ?
C2A C1A C5A . . 107.01(11) ?
O3A C2A C3A . . 124.94(13) ?
O3A C2A C1A . . 128.43(13) ?
C3A C2A C1A . . 106.56(11) ?
C4A C3A C2A . . 111.47(12) ?
C4A C3A H3A . . 124.3 ?
C2A C3A H3A . . 124.3 ?
C3A C4A C15A . . 125.03(12) ?
C3A C4A C5A . . 111.81(12) ?
C15A C4A C5A . . 123.08(12) ?
C6A C5A C4A . . 114.51(12) ?
C6A C5A C1A . . 112.21(11) ?
C4A C5A C1A . . 102.67(11) ?
C6A C5A H5A . . 109.1 ?
C4A C5A H5A . . 109.1 ?
C1A C5A H5A . . 109.1 ?
O1A C6A C5A . . 109.26(11) ?
O1A C6A C7A . . 103.13(11) ?
C5A C6A C7A . . 114.76(12) ?
O1A C6A H6A . . 109.8 ?
C5A C6A H6A . . 109.8 ?
C7A C6A H6A . . 109.8 ?
C8A C7A C6A . . 111.94(11) ?
C8A C7A C11A . . 118.10(12) ?
C6A C7A C11A . . 101.45(11) ?
C8A C7A H7A . . 108.3 ?
C6A C7A H7A . . 108.3 ?
C11A C7A H7A . . 108.3 ?
O4A C8A C7A . . 105.20(11) ?
O4A C8A C9A . . 107.00(11) ?
C7A C8A C9A . . 111.62(12) ?
O4A C8A H8A . . 110.9 ?
C7A C8A H8A . . 110.9 ?
C9A C8A H8A . . 110.9 ?
C10A C9A C8A . . 116.93(12) ?
C10A C9A H91A . . 108.1 ?
C8A C9A H91A . . 108.1 ?
C10A C9A H92A . . 108.1 ?
C8A C9A H92A . . 108.1 ?
H91A C9A H92A . . 107.3 ?
C1A C10A C14A . . 123.41(13) ?
C1A C10A C9A . . 123.36(13) ?
C14A C10A C9A . . 113.23(11) ?
C13A C11A C12A . . 112.04(13) ?
C13A C11A C7A . . 117.99(14) ?
C12A C11A C7A . . 101.17(11) ?
C13A C11A H11A . . 108.4 ?
C12A C11A H11A . . 108.4 ?
C7A C11A H11A . . 108.4 ?
O2A C12A O1A . . 121.52(13) ?
O2A C12A C11A . . 128.52(14) ?
O1A C12A C11A . . 109.96(12) ?
C11A C13A H13D . . 109.5 ?
C11A C13A H13E . . 109.5 ?
H13D C13A H13E . . 109.5 ?
C11A C13A H13F . . 109.5 ?
H13D C13A H13F . . 109.5 ?
H13E C13A H13F . . 109.5 ?
C10A C14A H14D . . 109.5 ?
C10A C14A H14E . . 109.5 ?
H14D C14A H14E . . 109.5 ?
C10A C14A H14F . . 109.5 ?
H14D C14A H14F . . 109.5 ?
H14E C14A H14F . . 109.5 ?
O6A C15A C4A . . 112.23(12) ?
O6A C15A H15C . . 109.2 ?
C4A C15A H15C . . 109.2 ?
O6A C15A H15D . . 109.2 ?
C4A C15A H15D . . 109.2 ?
H15C C15A H15D . . 107.9 ?
O5A C16A O4A . . 123.13(14) ?
O5A C16A C17A . . 125.78(14) ?
O4A C16A C17A . . 111.09(13) ?
C16A C17A H17D . . 109.5 ?
C16A C17A H17E . . 109.5 ?
H17D C17A H17E . . 109.5 ?
C16A C17A H17F . . 109.5 ?
H17D C17A H17F . . 109.5 ?
H17E C17A H17F . . 109.5 ?
H72 O7 H71 . . 106(2) ?
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 C12 . 1.3568(19) ?
O1 C6 . 1.4597(16) ?
O2 C12 . 1.194(2) ?
O3 C2 . 1.2251(19) ?
O4 C16 . 1.3496(18) ?
O4 C8 . 1.4598(16) ?
O5 C16 . 1.196(2) ?
O6 C15 . 1.4238(17) ?
O6 H6O . 0.86(2) ?
C1 C10 . 1.349(2) ?
C1 C2 . 1.500(2) ?
C1 C5 . 1.5264(19) ?
C2 C3 . 1.463(2) ?
C3 C4 . 1.334(2) ?
C3 H3 . 0.9500 ?
C4 C15 . 1.500(2) ?
C4 C5 . 1.5261(19) ?
C5 C6 . 1.525(2) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.5323(18) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.5177(19) ?
C7 C11 . 1.527(2) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.531(2) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.516(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C14 . 1.502(2) ?
C11 C12 . 1.520(2) ?
C11 C13 . 1.521(3) ?
C11 H11 . 1.0000 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.492(2) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
O1A C12A . 1.3524(18) ?
O1A C6A . 1.4612(16) ?
O2A C12A . 1.1982(19) ?
O3A C2A . 1.2259(18) ?
O4A C16A . 1.3445(18) ?
O4A C8A . 1.4586(16) ?
O5A C16A . 1.207(2) ?
O6A C15A . 1.4224(16) ?
O6A H60A . 0.85(2) ?
C1A C10A . 1.349(2) ?
C1A C2A . 1.4969(19) ?
C1A C5A . 1.5291(19) ?
C2A C3A . 1.4644(19) ?
C3A C4A . 1.328(2) ?
C3A H3A . 0.9500 ?
C4A C15A . 1.5041(19) ?
C4A C5A . 1.5271(18) ?
C5A C6A . 1.5238(19) ?
C5A H5A . 1.0000 ?
C6A C7A . 1.5337(18) ?
C6A H6A . 1.0000 ?
C7A C8A . 1.5182(19) ?
C7A C11A . 1.538(2) ?
C7A H7A . 1.0000 ?
C8A C9A . 1.530(2) ?
C8A H8A . 1.0000 ?
C9A C10A . 1.5206(19) ?
C9A H91A . 0.9900 ?
C9A H92A . 0.9900 ?
C10A C14A . 1.505(2) ?
C11A C13A . 1.513(2) ?
C11A C12A . 1.517(2) ?
C11A H11A . 1.0000 ?
C13A H13D . 0.9800 ?
C13A H13E . 0.9800 ?
C13A H13F . 0.9800 ?
C14A H14D . 0.9800 ?
C14A H14E . 0.9800 ?
C14A H14F . 0.9800 ?
C15A H15C . 0.9900 ?
C15A H15D . 0.9900 ?
C16A C17A . 1.490(2) ?
C17A H17D . 0.9800 ?
C17A H17E . 0.9800 ?
C17A H17F . 0.9800 ?
O7 H72 . 0.89(2) ?
O7 H71 . 0.89(3) ?
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
O6 H6O O7 . 0.86(2) 1.85(2) 2.6750(17) 160(2)
O6A H60A O6 . 0.85(2) 1.91(2) 2.7593(17) 174(2)
O7 H72 O5A 2_656 0.89(2) 1.95(2) 2.8160(18) 165(2)
O7 H71 O6A 1_565 0.89(3) 1.86(3) 2.7397(18) 176(3)
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
C10 C1 C2 O3 . . . . 1.9(3) ?
C5 C1 C2 O3 . . . . 179.40(15) ?
C10 C1 C2 C3 . . . . -179.34(14) ?
C5 C1 C2 C3 . . . . -1.83(16) ?
O3 C2 C3 C4 . . . . -179.83(14) ?
C1 C2 C3 C4 . . . . 1.35(17) ?
C2 C3 C4 C15 . . . . -176.29(14) ?
C2 C3 C4 C5 . . . . -0.30(18) ?
C3 C4 C5 C6 . . . . 117.53(15) ?
C15 C4 C5 C6 . . . . -66.36(18) ?
C3 C4 C5 C1 . . . . -0.85(16) ?
C15 C4 C5 C1 . . . . 175.27(13) ?
C10 C1 C5 C6 . . . . 57.39(19) ?
C2 C1 C5 C6 . . . . -120.12(13) ?
C10 C1 C5 C4 . . . . 179.11(15) ?
C2 C1 C5 C4 . . . . 1.60(15) ?
C12 O1 C6 C5 . . . . 149.85(14) ?
C12 O1 C6 C7 . . . . 26.24(17) ?
C4 C5 C6 O1 . . . . 48.63(17) ?
C1 C5 C6 O1 . . . . 163.25(11) ?
C4 C5 C6 C7 . . . . 165.59(12) ?
C1 C5 C6 C7 . . . . -79.78(15) ?
O1 C6 C7 C8 . . . . -163.07(12) ?
C5 C6 C7 C8 . . . . 75.57(16) ?
O1 C6 C7 C11 . . . . -36.96(15) ?
C5 C6 C7 C11 . . . . -158.32(13) ?
C16 O4 C8 C7 . . . . -135.67(13) ?
C16 O4 C8 C9 . . . . 104.36(14) ?
C11 C7 C8 O4 . . . . 56.71(17) ?
C6 C7 C8 O4 . . . . 173.63(12) ?
C11 C7 C8 C9 . . . . 173.60(13) ?
C6 C7 C8 C9 . . . . -69.48(16) ?
O4 C8 C9 C10 . . . . -166.64(12) ?
C7 C8 C9 C10 . . . . 76.91(16) ?
C2 C1 C10 C14 . . . . -2.7(2) ?
C5 C1 C10 C14 . . . . -179.77(14) ?
C2 C1 C10 C9 . . . . 178.21(14) ?
C5 C1 C10 C9 . . . . 1.2(2) ?
C8 C9 C10 C1 . . . . -60.8(2) ?
C8 C9 C10 C14 . . . . 120.02(14) ?
C8 C7 C11 C12 . . . . 156.71(14) ?
C6 C7 C11 C12 . . . . 33.66(17) ?
C8 C7 C11 C13 . . . . -82.6(2) ?
C6 C7 C11 C13 . . . . 154.36(15) ?
C6 O1 C12 O2 . . . . 175.77(18) ?
C6 O1 C12 C11 . . . . -4.1(2) ?
C13 C11 C12 O2 . . . . 35.0(3) ?
C7 C11 C12 O2 . . . . 160.5(2) ?
C13 C11 C12 O1 . . . . -145.13(17) ?
C7 C11 C12 O1 . . . . -19.7(2) ?
C3 C4 C15 O6 . . . . 6.5(2) ?
C5 C4 C15 O6 . . . . -169.07(13) ?
C8 O4 C16 O5 . . . . -1.4(2) ?
C8 O4 C16 C17 . . . . 177.21(12) ?
C10A C1A C2A O3A . . . . 11.1(2) ?
C5A C1A C2A O3A . . . . -171.14(15) ?
C10A C1A C2A C3A . . . . -171.77(15) ?
C5A C1A C2A C3A . . . . 6.04(16) ?
O3A C2A C3A C4A . . . . 174.67(15) ?
C1A C2A C3A C4A . . . . -2.63(18) ?
C2A C3A C4A C15A . . . . -178.68(14) ?
C2A C3A C4A C5A . . . . -1.99(18) ?
C3A C4A C5A C6A . . . . 127.48(14) ?
C15A C4A C5A C6A . . . . -55.76(19) ?
C3A C4A C5A C1A . . . . 5.58(16) ?
C15A C4A C5A C1A . . . . -177.65(13) ?
C10A C1A C5A C6A . . . . 47.5(2) ?
C2A C1A C5A C6A . . . . -130.28(12) ?
C10A C1A C5A C4A . . . . 170.90(15) ?
C2A C1A C5A C4A . . . . -6.84(15) ?
C12A O1A C6A C5A . . . . 146.40(12) ?
C12A O1A C6A C7A . . . . 23.91(15) ?
C4A C5A C6A O1A . . . . 52.01(16) ?
C1A C5A C6A O1A . . . . 168.54(11) ?
C4A C5A C6A C7A . . . . 167.24(12) ?
C1A C5A C6A C7A . . . . -76.23(15) ?
O1A C6A C7A C8A . . . . -162.59(12) ?
C5A C6A C7A C8A . . . . 78.68(16) ?
O1A C6A C7A C11A . . . . -35.75(14) ?
C5A C6A C7A C11A . . . . -154.48(12) ?
C16A O4A C8A C7A . . . . -158.28(12) ?
C16A O4A C8A C9A . . . . 82.89(15) ?
C6A C7A C8A O4A . . . . 172.54(11) ?
C11A C7A C8A O4A . . . . 55.30(16) ?
C6A C7A C8A C9A . . . . -71.77(16) ?
C11A C7A C8A C9A . . . . 170.99(13) ?
O4A C8A C9A C10A . . . . -170.91(12) ?
C7A C8A C9A C10A . . . . 74.50(16) ?
C2A C1A C10A C14A . . . . 4.0(2) ?
C5A C1A C10A C14A . . . . -173.31(14) ?
C2A C1A C10A C9A . . . . -175.04(13) ?
C5A C1A C10A C9A . . . . 7.6(2) ?
C8A C9A C10A C1A . . . . -59.5(2) ?
C8A C9A C10A C14A . . . . 121.36(14) ?
C8A C7A C11A C13A . . . . -80.60(18) ?
C6A C7A C11A C13A . . . . 156.70(14) ?
C8A C7A C11A C12A . . . . 156.85(13) ?
C6A C7A C11A C12A . . . . 34.14(15) ?
C6A O1A C12A O2A . . . . 179.11(15) ?
C6A O1A C12A C11A . . . . -1.34(17) ?
C13A C11A C12A O2A . . . . 31.4(2) ?
C7A C11A C12A O2A . . . . 157.96(17) ?
C13A C11A C12A O1A . . . . -148.13(14) ?
C7A C11A C12A O1A . . . . -21.55(16) ?
C3A C4A C15A O6A . . . . 12.0(2) ?
C5A C4A C15A O6A . . . . -164.31(13) ?
C8A O4A C16A O5A . . . . 2.9(2) ?
C8A O4A C16A C17A . . . . -177.12(12) ?
