#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151772.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_7151772
loop_
_publ_author_name
'Schanderl, Martin'
'Jeong, Won Boo'
'Schwarz, Michael'
'Reiser, Oliver'
_publ_section_title
;
 Stereoselective rearrangement of guaianolides to tricyclic
 δ-valerolactones.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2543
_journal_page_last               2547
_journal_paper_doi               10.1039/c0ob00919a
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C15 H20 O4'
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90
_cell_angle_beta                 95.532(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6695(5)
_cell_length_b                   13.7791(13)
_cell_length_c                   18.0400(17)
_cell_measurement_reflns_used    7034
_cell_measurement_temperature    297
_cell_measurement_theta_max      25.91
_cell_measurement_theta_min      1.86
_cell_volume                     1402.7(2)
_computing_cell_refinement       'STOE (1998)'
_computing_data_collection       'STOE (1998)'
_computing_data_reduction        'STOE (1998)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      297(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE-IPDS diffractometer'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19944
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.91
_diffrn_reflns_theta_max         25.91
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.788
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5396
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.788
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0615P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                2515
_reflns_number_total             5396
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0ob00919a.txt
_cod_data_source_block           i201
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7151772
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani -1.1080(5) -0.4638(2) -0.00332(18) 1.000 0.0854(11) . .
O2 O Uani -1.3139(6) -0.4758(2) -0.1121(2) 1.000 0.1134(17) . .
O3 O Uani -0.7437(5) -0.19222(18) -0.14426(13) 1.000 0.0694(10) . .
O4 O Uani -0.4019(6) -0.1911(3) -0.19507(14) 1.000 0.0960(13) . .
C1 C Uani -1.1483(8) -0.4372(3) -0.0755(3) 1.000 0.0825(19) . .
C2 C Uani -0.9831(7) -0.3680(3) -0.1074(2) 1.000 0.0745(14) . .
C3 C Uani -0.8414(6) -0.3040(3) -0.05089(18) 1.000 0.0589(11) . .
C4 C Uani -0.7409(6) -0.3679(2) 0.01310(19) 1.000 0.0568(11) . .
C5 C Uani -0.9500(6) -0.4094(3) 0.0496(2) 1.000 0.0634(14) . .
C6 C Uani -0.8789(8) -0.4728(3) 0.1160(2) 1.000 0.0789(16) . .
C7 C Uani -0.7286(8) -0.4135(3) 0.1737(2) 1.000 0.0813(17) . .
C8 C Uani -0.5097(7) -0.3736(3) 0.1408(2) 1.000 0.0776(16) . .
C9 C Uani -0.5690(6) -0.3164(3) 0.07009(18) 1.000 0.0570(12) . .
C10 C Uani -0.4718(6) -0.2318(3) 0.05396(18) 1.000 0.0586(12) . .
C11 C Uani -0.5210(7) -0.1831(3) -0.02144(19) 1.000 0.0642(12) . .
C12 C Uani -0.6404(6) -0.2492(3) -0.08084(18) 1.000 0.0598(12) . .
C13 C Uani -0.2982(7) -0.1753(3) 0.1057(2) 1.000 0.0761(14) . .
C14 C Uani -0.6063(7) -0.1691(3) -0.19788(19) 1.000 0.0629(14) . .
C15 C Uani -0.7414(8) -0.1136(3) -0.25911(19) 1.000 0.0855(16) . .
O5 O Uani -2.0704(5) -0.4704(2) -0.48172(16) 1.000 0.0806(11) . .
O6 O Uani -2.2899(6) -0.4884(2) -0.58805(18) 1.000 0.1039(14) . .
O7 O Uani -1.7363(5) -0.20532(18) -0.63752(12) 1.000 0.0687(10) . .
O8 O Uani -1.4143(6) -0.2144(3) -0.69702(14) 1.000 0.1082(16) . .
C16 C Uani -2.1235(8) -0.4473(3) -0.5541(3) 1.000 0.0756(16) . .
C17 C Uani -1.9657(7) -0.3783(3) -0.5908(2) 1.000 0.0721(14) . .
C18 C Uani -1.8176(6) -0.3115(3) -0.53894(17) 1.000 0.0542(11) . .
C19 C Uani -1.7076(6) -0.3715(2) -0.47320(18) 1.000 0.0534(11) . .
C20 C Uani -1.9087(6) -0.4114(3) -0.4331(2) 1.000 0.0606(12) . .
C21 C Uani -1.8288(7) -0.4707(3) -0.3654(2) 1.000 0.0751(17) . .
C22 C Uani -1.6768(7) -0.4062(3) -0.3110(2) 1.000 0.0759(16) . .
C23 C Uani -1.4660(7) -0.3671(3) -0.34797(19) 1.000 0.0729(14) . .
C24 C Uani -1.5327(6) -0.3157(3) -0.42037(18) 1.000 0.0541(11) . .
C25 C Uani -1.4404(6) -0.2322(3) -0.44165(18) 1.000 0.0584(12) . .
C26 C Uani -1.4982(7) -0.1890(3) -0.51820(19) 1.000 0.0645(12) . .
C27 C Uani -1.6236(6) -0.2586(3) -0.57381(17) 1.000 0.0553(11) . .
C28 C Uani -1.2680(7) -0.1712(3) -0.3929(2) 1.000 0.0750(16) . .
C29 C Uani -1.6159(8) -0.1897(3) -0.69555(18) 1.000 0.0641(15) . .
C30 C Uani -1.7563(8) -0.1366(3) -0.75575(18) 1.000 0.0810(15) . .
H2A H Uiso -1.07430 -0.32660 -0.14300 1.000 0.0890 calc R
H2B H Uiso -0.87330 -0.40470 -0.13440 1.000 0.0890 calc R
H3 H Uiso -0.94940 -0.25680 -0.03160 1.000 0.0710 calc R
H4 H Uiso -0.65660 -0.42190 -0.00780 1.000 0.0680 calc R
H5 H Uiso -1.04010 -0.35460 0.06700 1.000 0.0760 calc R
H6A H Uiso -0.78920 -0.52810 0.10090 1.000 0.0940 calc R
H6B H Uiso -1.01900 -0.49670 0.13700 1.000 0.0940 calc R
H7A H Uiso -0.67960 -0.45400 0.21650 1.000 0.0980 calc R
H7B H Uiso -0.82170 -0.36020 0.19050 1.000 0.0980 calc R
H8A H Uiso -0.42290 -0.33210 0.17740 1.000 0.0930 calc R
H8B H Uiso -0.40700 -0.42720 0.13040 1.000 0.0930 calc R
H11A H Uiso -0.62110 -0.12690 -0.01620 1.000 0.0770 calc R
H11B H Uiso -0.37240 -0.16030 -0.03760 1.000 0.0770 calc R
H12 H Uiso -0.52460 -0.29520 -0.09740 1.000 0.0720 calc R
H13A H Uiso -0.36870 -0.16050 0.15070 1.000 0.0910 calc R
H13B H Uiso -0.25740 -0.11610 0.08200 1.000 0.0910 calc R
H13C H Uiso -0.15780 -0.21340 0.11750 1.000 0.0910 calc R
H15A H Uiso -0.87160 -0.15220 -0.28050 1.000 0.1030 calc R
H15B H Uiso -0.63860 -0.09820 -0.29670 1.000 0.1030 calc R
H15C H Uiso -0.80080 -0.05470 -0.23950 1.000 0.1030 calc R
H17A H Uiso -2.06380 -0.33890 -0.62610 1.000 0.0870 calc R
H17B H Uiso -1.86020 -0.41590 -0.61890 1.000 0.0870 calc R
H18 H Uiso -1.92290 -0.26310 -0.51980 1.000 0.0650 calc R
H19 H Uiso -1.62360 -0.42640 -0.49310 1.000 0.0640 calc R
H20 H Uiso -1.99890 -0.35600 -0.41660 1.000 0.0730 calc R
H21A H Uiso -1.73740 -0.52610 -0.37950 1.000 0.0900 calc R
H21B H Uiso -1.96520 -0.49440 -0.34230 1.000 0.0900 calc R
H22A H Uiso -1.77120 -0.35260 -0.29540 1.000 0.0910 calc R
H22B H Uiso -1.62100 -0.44350 -0.26720 1.000 0.0910 calc R
H23A H Uiso -1.37860 -0.32260 -0.31390 1.000 0.0880 calc R
H23B H Uiso -1.36130 -0.42070 -0.35690 1.000 0.0880 calc R
H26A H Uiso -1.35220 -0.16760 -0.53700 1.000 0.0770 calc R
H26B H Uiso -1.59740 -0.13230 -0.51400 1.000 0.0770 calc R
H27 H Uiso -1.50980 -0.30540 -0.59060 1.000 0.0670 calc R
H28A H Uiso -1.33940 -0.15210 -0.34900 1.000 0.0900 calc R
H28B H Uiso -1.22750 -0.11430 -0.41970 1.000 0.0900 calc R
H28C H Uiso -1.12730 -0.20820 -0.37880 1.000 0.0900 calc R
H30A H Uiso -1.89630 -0.17300 -0.77180 1.000 0.0970 calc R
H30B H Uiso -1.66310 -0.12780 -0.79690 1.000 0.0970 calc R
H30C H Uiso -1.80080 -0.07430 -0.73760 1.000 0.0970 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 122.0(3) . . . yes
C12 O3 C14 118.5(3) . . . yes
C16 O5 C20 121.4(3) . . . yes
C27 O7 C29 119.1(3) . . . yes
O2 C1 C2 123.4(5) . . . yes
O1 C1 C2 119.4(4) . . . yes
O1 C1 O2 117.0(4) . . . yes
C1 C2 C3 115.1(3) . . . no
C2 C3 C4 108.0(3) . . . no
C2 C3 C12 114.8(3) . . . no
C4 C3 C12 108.7(3) . . . no
C3 C4 C5 107.2(3) . . . no
C5 C4 C9 111.0(3) . . . no
C3 C4 C9 114.3(3) . . . no
O1 C5 C6 108.9(3) . . . yes
O1 C5 C4 111.5(3) . . . yes
C4 C5 C6 113.7(3) . . . no
C5 C6 C7 108.8(3) . . . no
C6 C7 C8 110.5(3) . . . no
C7 C8 C9 113.1(3) . . . no
C8 C9 C10 125.3(3) . . . no
C4 C9 C8 113.8(3) . . . no
C4 C9 C10 120.8(3) . . . no
C9 C10 C13 125.2(3) . . . no
C11 C10 C13 112.3(3) . . . no
C9 C10 C11 122.5(3) . . . no
C10 C11 C12 113.5(3) . . . no
O3 C12 C11 110.4(3) . . . yes
O3 C12 C3 106.8(3) . . . yes
C3 C12 C11 110.4(3) . . . no
O3 C14 C15 111.4(3) . . . yes
O4 C14 C15 126.0(4) . . . yes
O3 C14 O4 122.6(3) . . . yes
C3 C2 H2A 108.00 . . . no
C1 C2 H2A 108.00 . . . no
C1 C2 H2B 109.00 . . . no
H2A C2 H2B 108.00 . . . no
C3 C2 H2B 108.00 . . . no
C4 C3 H3 108.00 . . . no
C12 C3 H3 108.00 . . . no
C2 C3 H3 108.00 . . . no
C9 C4 H4 108.00 . . . no
C3 C4 H4 108.00 . . . no
C5 C4 H4 108.00 . . . no
C6 C5 H5 107.00 . . . no
O1 C5 H5 107.00 . . . no
C4 C5 H5 108.00 . . . no
C5 C6 H6A 110.00 . . . no
C7 C6 H6B 110.00 . . . no
C5 C6 H6B 110.00 . . . no
C7 C6 H6A 110.00 . . . no
H6A C6 H6B 108.00 . . . no
C8 C7 H7A 110.00 . . . no
C8 C7 H7B 110.00 . . . no
H7A C7 H7B 108.00 . . . no
C6 C7 H7B 110.00 . . . no
C6 C7 H7A 110.00 . . . no
C9 C8 H8A 109.00 . . . no
C7 C8 H8A 109.00 . . . no
C7 C8 H8B 109.00 . . . no
H8A C8 H8B 108.00 . . . no
C9 C8 H8B 109.00 . . . no
C10 C11 H11B 109.00 . . . no
C10 C11 H11A 109.00 . . . no
H11A C11 H11B 108.00 . . . no
C12 C11 H11A 109.00 . . . no
C12 C11 H11B 109.00 . . . no
C11 C12 H12 110.00 . . . no
C3 C12 H12 110.00 . . . no
O3 C12 H12 110.00 . . . no
C10 C13 H13B 110.00 . . . no
C10 C13 H13A 109.00 . . . no
H13A C13 H13C 109.00 . . . no
C10 C13 H13C 109.00 . . . no
H13A C13 H13B 110.00 . . . no
H13B C13 H13C 109.00 . . . no
C14 C15 H15B 109.00 . . . no
C14 C15 H15C 110.00 . . . no
H15A C15 H15C 109.00 . . . no
H15B C15 H15C 109.00 . . . no
H15A C15 H15B 110.00 . . . no
C14 C15 H15A 109.00 . . . no
O5 C16 O6 117.9(4) . . . yes
O5 C16 C17 119.3(4) . . . yes
O6 C16 C17 122.7(4) . . . yes
C16 C17 C18 115.6(3) . . . no
C17 C18 C19 108.2(3) . . . no
C17 C18 C27 114.9(3) . . . no
C19 C18 C27 109.0(3) . . . no
C18 C19 C20 107.3(3) . . . no
C18 C19 C24 114.0(3) . . . no
C20 C19 C24 111.2(3) . . . no
O5 C20 C19 112.1(3) . . . yes
O5 C20 C21 108.0(3) . . . yes
C19 C20 C21 113.9(3) . . . no
C20 C21 C22 108.2(3) . . . no
C21 C22 C23 110.0(3) . . . no
C22 C23 C24 113.9(3) . . . no
C19 C24 C23 113.7(3) . . . no
C19 C24 C25 120.4(3) . . . no
C23 C24 C25 125.7(3) . . . no
C24 C25 C26 123.1(3) . . . no
C24 C25 C28 124.3(3) . . . no
C26 C25 C28 112.7(3) . . . no
C25 C26 C27 113.7(3) . . . no
O7 C27 C18 106.9(3) . . . yes
O7 C27 C26 110.2(3) . . . yes
C18 C27 C26 110.2(3) . . . no
O7 C29 O8 122.6(3) . . . yes
O7 C29 C30 112.4(4) . . . yes
O8 C29 C30 125.0(4) . . . yes
C16 C17 H17A 108.00 . . . no
C16 C17 H17B 108.00 . . . no
C18 C17 H17A 108.00 . . . no
C18 C17 H17B 108.00 . . . no
H17A C17 H17B 107.00 . . . no
C17 C18 H18 108.00 . . . no
C19 C18 H18 108.00 . . . no
C27 C18 H18 108.00 . . . no
C18 C19 H19 108.00 . . . no
C20 C19 H19 108.00 . . . no
C24 C19 H19 108.00 . . . no
O5 C20 H20 108.00 . . . no
C19 C20 H20 108.00 . . . no
C21 C20 H20 108.00 . . . no
C20 C21 H21A 110.00 . . . no
C20 C21 H21B 110.00 . . . no
C22 C21 H21A 110.00 . . . no
C22 C21 H21B 110.00 . . . no
H21A C21 H21B 108.00 . . . no
C21 C22 H22A 110.00 . . . no
C21 C22 H22B 110.00 . . . no
C23 C22 H22A 110.00 . . . no
C23 C22 H22B 110.00 . . . no
H22A C22 H22B 108.00 . . . no
C22 C23 H23A 109.00 . . . no
C22 C23 H23B 109.00 . . . no
C24 C23 H23A 109.00 . . . no
C24 C23 H23B 109.00 . . . no
H23A C23 H23B 108.00 . . . no
C25 C26 H26A 109.00 . . . no
C25 C26 H26B 109.00 . . . no
C27 C26 H26A 109.00 . . . no
C27 C26 H26B 109.00 . . . no
H26A C26 H26B 108.00 . . . no
O7 C27 H27 110.00 . . . no
C18 C27 H27 110.00 . . . no
C26 C27 H27 110.00 . . . no
C25 C28 H28A 109.00 . . . no
C25 C28 H28B 110.00 . . . no
C25 C28 H28C 110.00 . . . no
H28A C28 H28B 109.00 . . . no
H28A C28 H28C 109.00 . . . no
H28B C28 H28C 110.00 . . . no
C29 C30 H30A 110.00 . . . no
C29 C30 H30B 109.00 . . . no
C29 C30 H30C 109.00 . . . no
H30A C30 H30B 109.00 . . . no
H30A C30 H30C 109.00 . . . no
H30B C30 H30C 109.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.351(6) . . yes
O1 C5 1.453(5) . . yes
O2 C1 1.217(6) . . yes
O3 C12 1.463(4) . . yes
O3 C14 1.338(5) . . yes
O4 C14 1.194(5) . . yes
O5 C16 1.350(6) . . yes
O5 C20 1.455(5) . . yes
O6 C16 1.214(6) . . yes
O7 C27 1.458(4) . . yes
O7 C29 1.321(4) . . yes
O8 C29 1.195(6) . . yes
C1 C2 1.491(6) . . no
C2 C3 1.518(5) . . no
C3 C12 1.510(5) . . no
C3 C4 1.518(5) . . no
C4 C5 1.522(5) . . no
C4 C9 1.522(5) . . no
C5 C6 1.506(5) . . no
C6 C7 1.519(6) . . no
C7 C8 1.529(6) . . no
C8 C9 1.510(5) . . no
C9 C10 1.334(6) . . no
C10 C13 1.506(5) . . no
C10 C11 1.518(5) . . no
C11 C12 1.515(5) . . no
C14 C15 1.493(5) . . no
C2 H2A 0.9700 . . no
C2 H2B 0.9700 . . no
C3 H3 0.9800 . . no
C4 H4 0.9800 . . no
C5 H5 0.9800 . . no
C6 H6B 0.9700 . . no
C6 H6A 0.9700 . . no
C7 H7A 0.9700 . . no
C7 H7B 0.9700 . . no
C8 H8B 0.9700 . . no
C8 H8A 0.9700 . . no
C11 H11B 0.9700 . . no
C11 H11A 0.9700 . . no
C12 H12 0.9800 . . no
C13 H13B 0.9600 . . no
C13 H13A 0.9600 . . no
C13 H13C 0.9600 . . no
C15 H15C 0.9600 . . no
C15 H15A 0.9600 . . no
C15 H15B 0.9600 . . no
C16 C17 1.502(6) . . no
C17 C18 1.509(5) . . no
C18 C19 1.529(5) . . no
C18 C27 1.507(5) . . no
C19 C20 1.512(5) . . no
C19 C24 1.517(5) . . no
C20 C21 1.503(5) . . no
C21 C22 1.527(5) . . no
C22 C23 1.522(6) . . no
C23 C24 1.502(5) . . no
C24 C25 1.336(6) . . no
C25 C26 1.511(5) . . no
C25 C28 1.507(5) . . no
C26 C27 1.515(5) . . no
C29 C30 1.477(5) . . no
C17 H17A 0.9700 . . no
C17 H17B 0.9700 . . no
C18 H18 0.9800 . . no
C19 H19 0.9800 . . no
C20 H20 0.9800 . . no
C21 H21A 0.9700 . . no
C21 H21B 0.9700 . . no
C22 H22A 0.9700 . . no
C22 H22B 0.9700 . . no
C23 H23A 0.9700 . . no
C23 H23B 0.9700 . . no
C26 H26A 0.9700 . . no
C26 H26B 0.9700 . . no
C27 H27 0.9800 . . no
C28 H28A 0.9600 . . no
C28 H28B 0.9600 . . no
C28 H28C 0.9600 . . no
C30 H30A 0.9600 . . no
C30 H30B 0.9600 . . no
C30 H30C 0.9600 . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O2 C30 3.307(5) . 2_244 no
O4 C11 3.269(4) . . no
O6 C15 3.272(5) . 2_244 no
O8 C26 3.324(4) . . no
O1 H11A 2.7600 . 2_345 no
O2 H30B 2.6600 . 2_244 no
O2 H12 2.7800 . 1_455 no
O3 H2A 2.6400 . . no
O4 H2A 2.7400 . 1_655 no
O4 H11B 2.8600 . . no
O4 H23A 2.8200 . 1_655 no
O4 H28A 2.8800 . 1_655 no
O4 H12 2.4300 . . no
O5 H26B 2.9200 . 2_144 no
O6 H19 2.8000 . 1_455 no
O6 H15B 2.5700 . 2_244 no
O6 H26B 2.8200 . 2_144 no
O6 H27 2.8100 . 1_455 no
O7 H17A 2.6400 . . no
O8 H27 2.4000 . . no
O8 H8A 2.7800 . 1_454 no
O8 H13A 2.8800 . 1_454 no
O8 H17A 2.8400 . 1_655 no
C11 O4 3.269(4) . . no
C15 O6 3.272(5) . 2_254 no
C26 O8 3.324(4) . . no
C30 O2 3.307(5) . 2_254 no
C1 H4 2.9400 . . no
C1 H12 2.8900 . 1_455 no
C6 H8B 3.0900 . 1_455 no
C8 H13A 3.0400 . . no
C8 H13C 3.0300 . . no
C9 H12 3.0700 . . no
C9 H5 3.0500 . 1_655 no
C10 H3 3.0000 . . no
C10 H5 2.9700 . 1_655 no
C13 H8A 2.6500 . . no
C13 H5 2.9900 . 1_655 no
C13 H30B 2.9100 . 1_656 no
C13 H30A 3.0200 . 1_756 no
C14 H11B 3.0700 . . no
C15 H28A 2.9700 . 1_655 no
C16 H19 2.9500 . . no
C16 H27 2.9600 . 1_455 no
C20 H23B 3.0300 . 1_455 no
C23 H28A 3.0500 . . no
C23 H20 3.0300 . 1_655 no
C23 H28C 3.0000 . . no
C24 H20 3.0700 . 1_655 no
C24 H27 3.0900 . . no
C25 H20 3.0300 . 1_655 no
C25 H18 2.9800 . . no
C28 H15B 3.0200 . 1_455 no
C28 H23A 2.6400 . . no
C28 H15A 2.8900 . . no
C28 H20 3.0200 . 1_655 no
C30 H13A 2.9200 . 1_454 no
H2A O3 2.6400 . . no
H2A O4 2.7400 . 1_455 no
H2B H4 2.5000 . . no
H2B H12 2.5300 . . no
H3 C10 3.0000 . . no
H3 H11A 2.5800 . . no
H3 H5 2.3300 . . no
H4 H2B 2.5000 . . no
H4 H12 2.5400 . . no
H4 C1 2.9400 . . no
H5 H7B 2.4400 . . no
H5 H13C 2.2800 . 1_455 no
H5 C13 2.9900 . 1_455 no
H5 C9 3.0500 . 1_455 no
H5 C10 2.9700 . 1_455 no
H5 H3 2.3300 . . no
H6A H8B 2.5900 . . no
H6A H11B 2.3800 . 2_445 no
H6B H8B 2.3900 . 1_455 no
H6B H15C 2.3400 . 2_345 no
H7B H5 2.4400 . . no
H8A H13A 2.4400 . . no
H8A C13 2.6500 . . no
H8A H13C 2.5300 . . no
H8A O8 2.7800 . 1_656 no
H8B H6A 2.5900 . . no
H8B C6 3.0900 . 1_655 no
H8B H6B 2.3900 . 1_655 no
H11A H3 2.5800 . . no
H11A H13B 2.5900 . . no
H11A O1 2.7600 . 2_355 no
H11B C14 3.0700 . . no
H11B H13B 2.2800 . . no
H11B O4 2.8600 . . no
H11B H6A 2.3800 . 2_455 no
H12 H4 2.5400 . . no
H12 O4 2.4300 . . no
H12 O2 2.7800 . 1_655 no
H12 H2B 2.5300 . . no
H12 C1 2.8900 . 1_655 no
H12 C9 3.0700 . . no
H13A O8 2.8800 . 1_656 no
H13A C30 2.9200 . 1_656 no
H13A H8A 2.4400 . . no
H13A C8 3.0400 . . no
H13A H30B 2.0500 . 1_656 no
H13B H11B 2.2800 . . no
H13B H11A 2.5900 . . no
H13C C8 3.0300 . . no
H13C H8A 2.5300 . . no
H13C H30A 2.4300 . 1_756 no
H13C H5 2.2800 . 1_655 no
H15A H28C 2.3100 . . no
H15A C28 2.8900 . . no
H15B H28A 2.1500 . 1_655 no
H15B O6 2.5700 . 2_254 no
H15B C28 3.0200 . 1_655 no
H15C H6B 2.3400 . 2_355 no
H17A O7 2.6400 . . no
H17A O8 2.8400 . 1_455 no
H17B H19 2.5300 . . no
H17B H27 2.5200 . . no
H18 C25 2.9800 . . no
H18 H20 2.3300 . . no
H18 H26B 2.5700 . . no
H19 O6 2.8000 . 1_655 no
H19 C16 2.9500 . . no
H19 H17B 2.5300 . . no
H19 H21A 2.6000 . . no
H19 H27 2.5500 . . no
H20 C23 3.0300 . 1_455 no
H20 C24 3.0700 . 1_455 no
H20 C25 3.0300 . 1_455 no
H20 C28 3.0200 . 1_455 no
H20 H18 2.3300 . . no
H20 H22A 2.4300 . . no
H20 H23B 2.5700 . 1_455 no
H20 H28C 2.2900 . 1_455 no
H21A H19 2.6000 . . no
H21A H23B 2.5800 . . no
H21A H26A 2.5400 . 2_244 no
H21B H23B 2.4600 . 1_455 no
H21B H30C 2.3300 . 2_144 no
H22A H20 2.4300 . . no
H23A O4 2.8200 . 1_455 no
H23A C28 2.6400 . . no
H23A H28A 2.4500 . . no
H23A H28C 2.4900 . . no
H23B C20 3.0300 . 1_655 no
H23B H20 2.5700 . 1_655 no
H23B H21A 2.5800 . . no
H23B H21B 2.4600 . 1_655 no
H26A H28B 2.2900 . . no
H26A H21A 2.5400 . 2_254 no
H26B H18 2.5700 . . no
H26B H28B 2.5800 . . no
H26B O5 2.9200 . 2_154 no
H26B O6 2.8200 . 2_154 no
H27 O6 2.8100 . 1_655 no
H27 O8 2.4000 . . no
H27 C16 2.9600 . 1_655 no
H27 C24 3.0900 . . no
H27 H17B 2.5200 . . no
H27 H19 2.5500 . . no
H28A O4 2.8800 . 1_455 no
H28A C15 2.9700 . 1_455 no
H28A C23 3.0500 . . no
H28A H15B 2.1500 . 1_455 no
H28A H23A 2.4500 . . no
H28B H26A 2.2900 . . no
H28B H26B 2.5800 . . no
H28C C23 3.0000 . . no
H28C H15A 2.3100 . . no
H28C H20 2.2900 . 1_655 no
H28C H23A 2.4900 . . no
H30A C13 3.0200 . 1_354 no
H30A H13C 2.4300 . 1_354 no
H30B C13 2.9100 . 1_454 no
H30B H13A 2.0500 . 1_454 no
H30B O2 2.6600 . 2_254 no
H30C H21B 2.3300 . 2_154 no
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
C15 H15B O6 0.9600 2.5700 3.272(5) 130.00 2_254 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
C5 O1 C1 O2 -166.9(4) . . . . no
C5 O1 C1 C2 16.7(6) . . . . no
C1 O1 C5 C6 -161.3(4) . . . . no
C1 O1 C5 C4 -35.0(5) . . . . no
C12 O3 C14 C15 178.3(3) . . . . no
C12 O3 C14 O4 -1.9(6) . . . . no
C14 O3 C12 C11 86.6(4) . . . . no
C14 O3 C12 C3 -153.4(3) . . . . no
C20 O5 C16 O6 -167.0(4) . . . . no
C20 O5 C16 C17 17.6(5) . . . . no
C16 O5 C20 C19 -36.5(5) . . . . no
C16 O5 C20 C21 -162.7(3) . . . . no
C27 O7 C29 O8 -2.8(6) . . . . no
C27 O7 C29 C30 178.9(3) . . . . no
C29 O7 C27 C18 -149.7(3) . . . . no
C29 O7 C27 C26 90.6(4) . . . . no
O1 C1 C2 C3 -22.7(5) . . . . no
O2 C1 C2 C3 161.2(4) . . . . no
C1 C2 C3 C12 168.1(3) . . . . no
C1 C2 C3 C4 46.6(4) . . . . no
C4 C3 C12 O3 177.5(3) . . . . no
C12 C3 C4 C5 171.2(3) . . . . no
C12 C3 C4 C9 47.8(4) . . . . no
C2 C3 C4 C5 -63.7(3) . . . . no
C4 C3 C12 C11 -62.5(4) . . . . no
C2 C3 C4 C9 172.9(3) . . . . no
C2 C3 C12 O3 56.4(4) . . . . no
C2 C3 C12 C11 176.5(3) . . . . no
C9 C4 C5 O1 -176.5(3) . . . . no
C3 C4 C9 C10 -16.5(5) . . . . no
C3 C4 C5 O1 58.0(4) . . . . no
C3 C4 C5 C6 -178.4(3) . . . . no
C3 C4 C9 C8 168.0(3) . . . . no
C5 C4 C9 C8 46.7(4) . . . . no
C5 C4 C9 C10 -137.9(3) . . . . no
C9 C4 C5 C6 -52.9(4) . . . . no
O1 C5 C6 C7 -175.9(3) . . . . no
C4 C5 C6 C7 59.2(4) . . . . no
C5 C6 C7 C8 -58.3(4) . . . . no
C6 C7 C8 C9 54.5(4) . . . . no
C7 C8 C9 C10 136.0(4) . . . . no
C7 C8 C9 C4 -48.8(4) . . . . no
C4 C9 C10 C13 -179.3(3) . . . . no
C8 C9 C10 C11 173.6(3) . . . . no
C8 C9 C10 C13 -4.4(6) . . . . no
C4 C9 C10 C11 -1.3(5) . . . . no
C13 C10 C11 C12 164.7(3) . . . . no
C9 C10 C11 C12 -13.6(5) . . . . no
C10 C11 C12 C3 45.6(4) . . . . no
C10 C11 C12 O3 163.5(3) . . . . no
O6 C16 C17 C18 162.2(4) . . . . no
O5 C16 C17 C18 -22.6(5) . . . . no
C16 C17 C18 C27 167.3(3) . . . . no
C16 C17 C18 C19 45.2(4) . . . . no
C17 C18 C27 C26 176.2(3) . . . . no
C17 C18 C19 C20 -62.5(3) . . . . no
C27 C18 C19 C20 171.9(3) . . . . no
C19 C18 C27 O7 178.1(3) . . . . no
C19 C18 C27 C26 -62.2(4) . . . . no
C27 C18 C19 C24 48.3(4) . . . . no
C17 C18 C27 O7 56.5(4) . . . . no
C17 C18 C19 C24 173.9(3) . . . . no
C18 C19 C20 O5 58.4(4) . . . . no
C20 C19 C24 C23 45.9(4) . . . . no
C18 C19 C20 C21 -178.6(3) . . . . no
C24 C19 C20 O5 -176.3(3) . . . . no
C20 C19 C24 C25 -138.5(3) . . . . no
C18 C19 C24 C23 167.3(3) . . . . no
C18 C19 C24 C25 -17.1(5) . . . . no
C24 C19 C20 C21 -53.4(4) . . . . no
C19 C20 C21 C22 59.9(4) . . . . no
O5 C20 C21 C22 -175.0(3) . . . . no
C20 C21 C22 C23 -58.4(4) . . . . no
C21 C22 C23 C24 54.2(4) . . . . no
C22 C23 C24 C25 136.7(4) . . . . no
C22 C23 C24 C19 -48.0(4) . . . . no
C19 C24 C25 C26 -1.0(5) . . . . no
C19 C24 C25 C28 179.3(3) . . . . no
C23 C24 C25 C26 174.0(3) . . . . no
C23 C24 C25 C28 -5.7(6) . . . . no
C28 C25 C26 C27 166.5(3) . . . . no
C24 C25 C26 C27 -13.2(5) . . . . no
C25 C26 C27 O7 162.6(3) . . . . no
C25 C26 C27 C18 44.9(4) . . . . no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190612
