#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227587.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_2227587
loop_
_publ_author_name
'He, Chao-Jun'
'Wang, Min'
'Sun, Hua'
'Liu, Zeng-bing'
'Fu, Yu-wan'
_publ_section_title
;
 12β,14-Dihydroxy-3-oxo-5β,20(22)-cardenolide monohydrate
;
_journal_coeditor_code           HG2696
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2704
_journal_paper_doi               10.1107/S1600536810038031
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H30 O5, H2 O'
_chemical_formula_moiety         'C23 H30 O5, H2 O'
_chemical_formula_sum            'C23 H32 O6'
_chemical_formula_weight         404.49
_chemical_name_systematic
;
12β,14-Dihydroxy-3-oxo-5β,20(22)-cardenolide monohydrate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.51(3)
_cell_angle_beta                 94.70(3)
_cell_angle_gamma                114.97(3)
_cell_formula_units_Z            1
_cell_length_a                   7.4017(15)
_cell_length_b                   7.7450(15)
_cell_length_c                   10.215(2)
_cell_measurement_reflns_used    1642
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.795
_cell_measurement_theta_min      2.051
_cell_volume                     516.0(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5251
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             218
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.140
_refine_ls_extinction_coef       0.43(3)
_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   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0344
_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)+(0.0504P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                1443
_reflns_number_total             1809
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg2696.cif
_cod_data_source_block           I
_cod_database_code               2227587
_cod_database_fobs_code          2227587
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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
C C1 -0.0073(4) 0.3043(5) 0.5686(3) 0.0474(8) Uani d . 1 . .
H H1A -0.1000 0.3610 0.5551 0.057 Uiso calc R 1 . .
H H1B -0.0281 0.2103 0.4864 0.057 Uiso calc R 1 . .
C C2 -0.0581(5) 0.1979(5) 0.6826(3) 0.0566(9) Uani d . 1 . .
H H2A -0.0574 0.2868 0.7618 0.068 Uiso calc R 1 . .
H H2B -0.1931 0.0907 0.6569 0.068 Uiso calc R 1 . .
C C3 0.0884(5) 0.1203(5) 0.7161(3) 0.0562(9) Uani d . 1 . .
C C4 0.2931(5) 0.2275(5) 0.6930(3) 0.0548(8) Uani d . 1 . .
H H4 0.3868 0.1813 0.7137 0.066 Uiso calc R 1 . .
C C5 0.3553(4) 0.3895(4) 0.6435(3) 0.0394(7) Uani d . 1 . .
C C6 0.5751(4) 0.5096(5) 0.6423(3) 0.0510(8) Uani d . 1 . .
H H6A 0.6496 0.4382 0.6646 0.061 Uiso calc R 1 . .
H H6B 0.6252 0.6295 0.7107 0.061 Uiso calc R 1 . .
C C7 0.6133(4) 0.5598(5) 0.5056(3) 0.0426(7) Uani d . 1 . .
H H7A 0.5823 0.4415 0.4395 0.051 Uiso calc R 1 . .
H H7B 0.7552 0.6476 0.5118 0.051 Uiso calc R 1 . .
C C8 0.4846(4) 0.6561(4) 0.4589(3) 0.0302(6) Uani d . 1 . .
H H8 0.5236 0.7780 0.5253 0.036 Uiso calc R 1 . .
C C9 0.2593(3) 0.5255(4) 0.4572(3) 0.0299(6) Uani d . 1 . .
H H9 0.2219 0.4043 0.3906 0.036 Uiso calc R 1 . .
C C10 0.2105(4) 0.4666(3) 0.5934(2) 0.0321(6) Uani d . 1 . .
C C11 0.1312(4) 0.6216(4) 0.4064(3) 0.0380(7) Uani d . 1 . .
H H11A -0.0108 0.5345 0.4005 0.046 Uiso calc R 1 . .
H H11B 0.1622 0.7411 0.4712 0.046 Uiso calc R 1 . .
C C12 0.1679(4) 0.6685(4) 0.2704(3) 0.0333(6) Uani d . 1 . .
H H12 0.1254 0.5461 0.2038 0.040 Uiso calc R 1 . .
C C13 0.3939(4) 0.8041(3) 0.2682(2) 0.0302(6) Uani d . 1 . .
C C14 0.5248(4) 0.7098(4) 0.3221(3) 0.0311(6) Uani d . 1 . .
C C15 0.4892(4) 0.5418(4) 0.2060(3) 0.0364(6) Uani d . 1 . .
H H15A 0.3658 0.4274 0.2068 0.044 Uiso calc R 1 . .
H H15B 0.6013 0.5080 0.2116 0.044 Uiso calc R 1 . .
C C16 0.4720(4) 0.6179(4) 0.0779(3) 0.0441(7) Uani d . 1 . .
H H16A 0.3672 0.5153 0.0083 0.053 Uiso calc R 1 . .
H H16B 0.5991 0.6614 0.0442 0.053 Uiso calc R 1 . .
C C17 0.4186(4) 0.7903(4) 0.1164(3) 0.0350(6) Uani d . 1 . .
H H17 0.2852 0.7522 0.0644 0.042 Uiso calc R 1 . .
C C18 0.2350(5) 0.6415(5) 0.7033(3) 0.0507(8) Uani d . 1 . .
H H18A 0.2182 0.6027 0.7878 0.076 Uiso calc R 1 . .
H H18B 0.1346 0.6836 0.6789 0.076 Uiso calc R 1 . .
H H18C 0.3674 0.7469 0.7116 0.076 Uiso calc R 1 . .
C C19 0.4521(4) 1.0101(4) 0.3480(3) 0.0418(7) Uani d . 1 . .
H H19A 0.5941 1.0896 0.3529 0.063 Uiso calc R 1 . .
H H19B 0.4220 1.0049 0.4373 0.063 Uiso calc R 1 . .
H H19C 0.3767 1.0654 0.3039 0.063 Uiso calc R 1 . .
C C20 0.5633(4) 0.9736(4) 0.0803(3) 0.0380(6) Uani d . 1 . .
C C21 0.7889(4) 1.0689(4) 0.1180(4) 0.0567(9) Uani d . 1 . .
H H21A 0.8296 1.1136 0.2150 0.068 Uiso calc R 1 . .
H H21B 0.8434 0.9787 0.0863 0.068 Uiso calc R 1 . .
C C22 0.5139(5) 1.0757(4) 0.0035(3) 0.0488(8) Uani d . 1 . .
H H22 0.3828 1.0478 -0.0331 0.059 Uiso calc R 1 . .
C C23 0.6953(5) 1.2364(4) -0.0143(3) 0.0523(8) Uani d . 1 . .
O O1 0.0400(5) -0.0230(4) 0.7666(3) 0.0905(10) Uani d . 1 . .
O O2 0.0392(3) 0.7578(3) 0.2377(2) 0.0497(6) Uani d . 1 . .
H H2 0.0251 0.7534 0.1566 0.075 Uiso calc R 1 . .
O O3 0.7324(2) 0.8562(2) 0.33978(19) 0.0392(5) Uani d . 1 . .
H H3 0.8017 0.8051 0.3095 0.059 Uiso calc R 1 . .
O O4 0.8586(3) 1.2327(3) 0.0526(2) 0.0610(6) Uani d . 1 . .
O O5 0.7166(4) 1.3617(4) -0.0773(3) 0.0797(8) Uani d . 1 . .
O O6 0.9639(4) 0.7538(4) 0.9630(3) 0.0661(7) Uani d D 1 . .
H H1W 0.979(7) 0.816(5) 0.899(3) 0.105(15) Uiso d D 1 . .
H H2W 0.901(7) 0.6285(16) 0.937(4) 0.13(2) Uiso d 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 0.0033 0.0016 '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 0.0106 0.0060 '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 C1 C10 . . 113.8(2) ?
C2 C1 H1A . . 108.8 ?
C10 C1 H1A . . 108.8 ?
C2 C1 H1B . . 108.8 ?
C10 C1 H1B . . 108.8 ?
H1A C1 H1B . . 107.7 ?
C3 C2 C1 . . 111.8(3) ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
H2A C2 H2B . . 107.9 ?
O1 C3 C4 . . 121.6(3) ?
O1 C3 C2 . . 121.4(3) ?
C4 C3 C2 . . 116.9(3) ?
C5 C4 C3 . . 123.9(3) ?
C5 C4 H4 . . 118.1 ?
C3 C4 H4 . . 118.1 ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 C10 . . 122.4(3) ?
C6 C5 C10 . . 116.7(2) ?
C5 C6 C7 . . 112.2(2) ?
C5 C6 H6A . . 109.2 ?
C7 C6 H6A . . 109.2 ?
C5 C6 H6B . . 109.2 ?
C7 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C6 C7 C8 . . 111.6(2) ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
C7 C8 C14 . . 111.8(2) ?
C7 C8 C9 . . 110.3(2) ?
C14 C8 C9 . . 112.24(18) ?
C7 C8 H8 . . 107.4 ?
C14 C8 H8 . . 107.4 ?
C9 C8 H8 . . 107.4 ?
C11 C9 C8 . . 109.72(19) ?
C11 C9 C10 . . 112.22(19) ?
C8 C9 C10 . . 114.26(19) ?
C11 C9 H9 . . 106.7 ?
C8 C9 H9 . . 106.7 ?
C10 C9 H9 . . 106.7 ?
C5 C10 C1 . . 109.3(2) ?
C5 C10 C18 . . 107.8(2) ?
C1 C10 C18 . . 110.2(2) ?
C5 C10 C9 . . 109.2(2) ?
C1 C10 C9 . . 108.2(2) ?
C18 C10 C9 . . 112.1(2) ?
C12 C11 C9 . . 112.8(2) ?
C12 C11 H11A . . 109.0 ?
C9 C11 H11A . . 109.0 ?
C12 C11 H11B . . 109.0 ?
C9 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
O2 C12 C11 . . 106.0(2) ?
O2 C12 C13 . . 111.4(2) ?
C11 C12 C13 . . 113.1(2) ?
O2 C12 H12 . . 108.7 ?
C11 C12 H12 . . 108.7 ?
C13 C12 H12 . . 108.7 ?
C19 C13 C14 . . 113.6(2) ?
C19 C13 C12 . . 110.0(2) ?
C14 C13 C12 . . 108.13(19) ?
C19 C13 C17 . . 114.5(2) ?
C14 C13 C17 . . 103.33(19) ?
C12 C13 C17 . . 106.8(2) ?
O3 C14 C15 . . 108.79(19) ?
O3 C14 C8 . . 107.92(19) ?
C15 C14 C8 . . 116.0(2) ?
O3 C14 C13 . . 105.59(19) ?
C15 C14 C13 . . 104.0(2) ?
C8 C14 C13 . . 113.95(19) ?
C14 C15 C16 . . 105.1(2) ?
C14 C15 H15A . . 110.7 ?
C16 C15 H15A . . 110.7 ?
C14 C15 H15B . . 110.7 ?
C16 C15 H15B . . 110.7 ?
H15A C15 H15B . . 108.8 ?
C15 C16 C17 . . 107.2(2) ?
C15 C16 H16A . . 110.3 ?
C17 C16 H16A . . 110.3 ?
C15 C16 H16B . . 110.3 ?
C17 C16 H16B . . 110.3 ?
H16A C16 H16B . . 108.5 ?
C20 C17 C16 . . 112.9(2) ?
C20 C17 C13 . . 116.6(2) ?
C16 C17 C13 . . 105.62(19) ?
C20 C17 H17 . . 107.1 ?
C16 C17 H17 . . 107.1 ?
C13 C17 H17 . . 107.1 ?
C10 C18 H18A . . 109.5 ?
C10 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C10 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C13 C19 H19A . . 109.5 ?
C13 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C13 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C22 C20 C21 . . 107.7(2) ?
C22 C20 C17 . . 125.9(3) ?
C21 C20 C17 . . 126.4(2) ?
O4 C21 C20 . . 105.0(2) ?
O4 C21 H21A . . 110.7 ?
C20 C21 H21A . . 110.7 ?
O4 C21 H21B . . 110.7 ?
C20 C21 H21B . . 110.7 ?
H21A C21 H21B . . 108.8 ?
C20 C22 C23 . . 109.6(3) ?
C20 C22 H22 . . 125.2 ?
C23 C22 H22 . . 125.2 ?
O5 C23 O4 . . 120.3(3) ?
O5 C23 C22 . . 130.4(3) ?
O4 C23 C22 . . 109.3(2) ?
C12 O2 H2 . . 109.5 ?
C14 O3 H3 . . 109.5 ?
C23 O4 C21 . . 108.4(2) ?
H1W O6 H2W . . 114.3(19) ?
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
C1 C2 . 1.518(4) ?
C1 C10 . 1.536(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.487(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O1 . 1.229(4) ?
C3 C4 . 1.450(5) ?
C4 C5 . 1.342(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.497(4) ?
C5 C10 . 1.523(3) ?
C6 C7 . 1.527(4) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.528(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C14 . 1.539(3) ?
C8 C9 . 1.540(3) ?
C8 H8 . 0.9800 ?
C9 C11 . 1.537(3) ?
C9 C10 . 1.558(3) ?
C9 H9 . 0.9800 ?
C10 C18 . 1.544(4) ?
C11 C12 . 1.510(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O2 . 1.442(3) ?
C12 C13 . 1.560(3) ?
C12 H12 . 0.9800 ?
C13 C19 . 1.526(4) ?
C13 C14 . 1.555(3) ?
C13 C17 . 1.567(3) ?
C14 O3 . 1.448(3) ?
C14 C15 . 1.523(4) ?
C15 C16 . 1.538(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.547(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C20 . 1.501(4) ?
C17 H17 . 0.9800 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 C22 . 1.333(4) ?
C20 C21 . 1.497(4) ?
C21 O4 . 1.451(3) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 C23 . 1.445(4) ?
C22 H22 . 0.9300 ?
C23 O5 . 1.215(4) ?
C23 O4 . 1.352(4) ?
O2 H2 . 0.8200 ?
O3 H3 . 0.8200 ?
O6 H1W . 0.861(11) ?
O6 H2W . 0.862(11) ?
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
O2 H2 O6 1_454 0.82 1.99 2.808(3) 172.7
O3 H3 O2 1_655 0.82 2.10 2.900(3) 163.6
O6 H1W O1 1_665 0.861(11) 1.943(11) 2.801(3) 174(4)
O6 H2W O5 1_546 0.862(11) 1.908(18) 2.741(4) 162(5)
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 C3 . . . . -54.0(4) ?
C1 C2 C3 O1 . . . . -153.4(3) ?
C1 C2 C3 C4 . . . . 29.7(4) ?
O1 C3 C4 C5 . . . . -177.1(3) ?
C2 C3 C4 C5 . . . . -0.2(5) ?
C3 C4 C5 C6 . . . . 170.4(3) ?
C3 C4 C5 C10 . . . . -6.1(5) ?
C4 C5 C6 C7 . . . . 131.9(3) ?
C10 C5 C6 C7 . . . . -51.3(4) ?
C5 C6 C7 C8 . . . . 53.6(4) ?
C6 C7 C8 C14 . . . . 179.2(2) ?
C6 C7 C8 C9 . . . . -55.2(3) ?
C7 C8 C9 C11 . . . . -178.5(3) ?
C14 C8 C9 C11 . . . . -53.1(3) ?
C7 C8 C9 C10 . . . . 54.5(3) ?
C14 C8 C9 C10 . . . . 179.9(2) ?
C4 C5 C10 C1 . . . . -17.3(4) ?
C6 C5 C10 C1 . . . . 166.1(3) ?
C4 C5 C10 C18 . . . . 102.6(3) ?
C6 C5 C10 C18 . . . . -74.1(3) ?
C4 C5 C10 C9 . . . . -135.4(3) ?
C6 C5 C10 C9 . . . . 47.9(3) ?
C2 C1 C10 C5 . . . . 46.7(3) ?
C2 C1 C10 C18 . . . . -71.5(3) ?
C2 C1 C10 C9 . . . . 165.6(2) ?
C11 C9 C10 C5 . . . . -175.0(2) ?
C8 C9 C10 C5 . . . . -49.3(3) ?
C11 C9 C10 C1 . . . . 66.1(3) ?
C8 C9 C10 C1 . . . . -168.16(19) ?
C11 C9 C10 C18 . . . . -55.6(3) ?
C8 C9 C10 C18 . . . . 70.1(3) ?
C8 C9 C11 C12 . . . . 55.3(3) ?
C10 C9 C11 C12 . . . . -176.6(2) ?
C9 C11 C12 O2 . . . . -179.6(2) ?
C9 C11 C12 C13 . . . . -57.3(3) ?
O2 C12 C13 C19 . . . . 48.2(3) ?
C11 C12 C13 C19 . . . . -71.1(3) ?
O2 C12 C13 C14 . . . . 172.8(2) ?
C11 C12 C13 C14 . . . . 53.5(3) ?
O2 C12 C13 C17 . . . . -76.6(2) ?
C11 C12 C13 C17 . . . . 164.1(2) ?
C7 C8 C14 O3 . . . . -64.4(3) ?
C9 C8 C14 O3 . . . . 171.01(18) ?
C7 C8 C14 C15 . . . . 57.9(3) ?
C9 C8 C14 C15 . . . . -66.7(3) ?
C7 C8 C14 C13 . . . . 178.7(2) ?
C9 C8 C14 C13 . . . . 54.1(3) ?
C19 C13 C14 O3 . . . . -48.0(3) ?
C12 C13 C14 O3 . . . . -170.35(19) ?
C17 C13 C14 O3 . . . . 76.7(2) ?
C19 C13 C14 C15 . . . . -162.5(2) ?
C12 C13 C14 C15 . . . . 75.2(2) ?
C17 C13 C14 C15 . . . . -37.8(2) ?
C19 C13 C14 C8 . . . . 70.3(3) ?
C12 C13 C14 C8 . . . . -52.1(3) ?
C17 C13 C14 C8 . . . . -165.0(2) ?
O3 C14 C15 C16 . . . . -75.9(2) ?
C8 C14 C15 C16 . . . . 162.2(2) ?
C13 C14 C15 C16 . . . . 36.3(2) ?
C14 C15 C16 C17 . . . . -20.6(3) ?
C15 C16 C17 C20 . . . . 125.5(2) ?
C15 C16 C17 C13 . . . . -3.0(3) ?
C19 C13 C17 C20 . . . . 22.6(3) ?
C14 C13 C17 C20 . . . . -101.5(2) ?
C12 C13 C17 C20 . . . . 144.6(2) ?
C19 C13 C17 C16 . . . . 148.9(2) ?
C14 C13 C17 C16 . . . . 24.8(2) ?
C12 C13 C17 C16 . . . . -89.1(2) ?
C16 C17 C20 C22 . . . . 124.3(3) ?
C13 C17 C20 C22 . . . . -113.1(3) ?
C16 C17 C20 C21 . . . . -52.4(4) ?
C13 C17 C20 C21 . . . . 70.1(4) ?
C22 C20 C21 O4 . . . . -0.7(3) ?
C17 C20 C21 O4 . . . . 176.6(2) ?
C21 C20 C22 C23 . . . . 0.4(3) ?
C17 C20 C22 C23 . . . . -176.9(2) ?
C20 C22 C23 O5 . . . . 179.4(3) ?
C20 C22 C23 O4 . . . . 0.1(3) ?
O5 C23 O4 C21 . . . . -179.9(3) ?
C22 C23 O4 C21 . . . . -0.5(3) ?
C20 C21 O4 C23 . . . . 0.7(3) ?
loop_
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1 ChemSpider 30656253
