#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/71/2227118.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_2227118
loop_
_publ_author_name
'Świzdor, Alina'
'Białońska, Agata'
'Kołek, Teresa'
'Panek, Anna'
_publ_section_title
;
 3β,11α-Dihydroxy-17a-oxa-<small>D</small>-homoandrost-5-en-17-one
;
_journal_coeditor_code           WN2398
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2003
_journal_paper_doi               10.1107/S1600536810026516
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H28 O4'
_chemical_formula_moiety         'C19 H28 O4'
_chemical_formula_sum            'C19 H28 O4'
_chemical_formula_weight         320.41
_chemical_name_systematic
;
3β,11α-Dihydroxy-17a-oxa-D-homoandrost-5-en-17-one
;
_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                90.00
_cell_angle_beta                 102.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.915(3)
_cell_length_b                   9.854(2)
_cell_length_c                   14.246(3)
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      3.06
_cell_volume                     1632.0(7)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'XP (Bruker, 1999)'
_computing_publication_material  'SHELXTL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_av_sigmaI/netI    0.1358
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8286
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0918
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1673
_reflns_number_gt                2062
_reflns_number_total             2921
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wn2398.cif
_cod_data_source_block           I
_cod_original_cell_volume        1632.0(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2227118
_cod_database_fobs_code          2227118
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
C C1 0.9668(6) -0.0351(9) 0.8744(7) 0.027(2) Uani d . 1 . .
H H1A 0.9251 -0.1158 0.8433 0.033 Uiso calc R 1 . .
H H1B 0.9861 -0.0514 0.9446 0.033 Uiso calc R 1 . .
C C2 1.0803(7) -0.0189(9) 0.8385(7) 0.029(2) Uani d . 1 . .
H H2A 1.1256 0.0572 0.8731 0.035 Uiso calc R 1 . .
H H2B 1.1267 -0.1027 0.8529 0.035 Uiso calc R 1 . .
C C3 1.0566(7) 0.0076(9) 0.7341(7) 0.025(2) Uani d . 1 . .
H H3 1.0206 -0.0751 0.6994 0.031 Uiso calc R 1 . .
O O3 1.1595(4) 0.0405(6) 0.7006(4) 0.0286(16) Uani d . 1 . .
H H31 1.1968 -0.0308 0.6967 0.043 Uiso calc R 1 . .
C C4 0.9758(7) 0.1260(9) 0.7066(7) 0.029(2) Uani d . 1 . .
H H4A 0.9538 0.1320 0.6355 0.035 Uiso calc R 1 . .
H H4B 1.0169 0.2107 0.7306 0.035 Uiso calc R 1 . .
C C5 0.8679(7) 0.1160(8) 0.7455(7) 0.024(2) Uani d . 1 . .
C C6 0.7672(8) 0.1263(10) 0.6882(7) 0.037(3) Uani d . 1 . .
H H6 0.7643 0.1284 0.6210 0.045 Uiso calc R 1 . .
C C7 0.6540(6) 0.1352(9) 0.7199(6) 0.023(2) Uani d . 1 . .
H H7A 0.6109 0.0493 0.7042 0.028 Uiso calc R 1 . .
H H7B 0.6070 0.2097 0.6849 0.028 Uiso calc R 1 . .
C C8 0.6749(6) 0.1611(8) 0.8280(6) 0.0162(19) Uani d . 1 . .
H H8 0.7060 0.2553 0.8404 0.019 Uiso calc R 1 . .
C C9 0.7686(6) 0.0604(8) 0.8813(6) 0.019(2) Uani d . 1 . .
H H9 0.7440 -0.0321 0.8561 0.023 Uiso calc R 1 . .
C C10 0.8868(6) 0.0897(8) 0.8531(6) 0.0157(19) Uani d . 1 . .
C C11 0.7781(6) 0.0549(9) 0.9891(6) 0.023(2) Uani d . 1 . .
H H11 0.8203 0.1382 1.0173 0.027 Uiso calc R 1 . .
O O11 0.8426(4) -0.0592(6) 1.0332(4) 0.0259(14) Uani d . 1 . .
H H111 0.8013 -0.1290 1.0235 0.039 Uiso calc R 1 . .
C C12 0.6615(6) 0.0549(9) 1.0183(7) 0.024(2) Uani d . 1 . .
H H12A 0.6226 -0.0330 1.0001 0.029 Uiso calc R 1 . .
H H12B 0.6744 0.0643 1.0891 0.029 Uiso calc R 1 . .
C C13 0.5839(6) 0.1694(8) 0.9707(6) 0.020(2) Uani d . 1 . .
C C14 0.5621(6) 0.1529(9) 0.8640(6) 0.020(2) Uani d . 1 . .
H H14 0.5312 0.0591 0.8493 0.024 Uiso calc R 1 . .
C C15 0.4689(7) 0.2504(8) 0.8136(7) 0.027(2) Uani d . 1 . .
H H15A 0.4964 0.3451 0.8248 0.033 Uiso calc R 1 . .
H H15B 0.4515 0.2332 0.7435 0.033 Uiso calc R 1 . .
C C16 0.3611(6) 0.2308(9) 0.8522(6) 0.024(2) Uani d . 1 . .
H H16A 0.3152 0.3152 0.8396 0.028 Uiso calc R 1 . .
H H16B 0.3152 0.1577 0.8143 0.028 Uiso calc R 1 . .
C C17 0.3752(7) 0.1970(8) 0.9557(7) 0.023(2) Uani d . 1 . .
O O17 0.2973(5) 0.2021(6) 0.9997(4) 0.0292(15) Uani d . 1 . .
C C18 0.6319(7) 0.3083(9) 1.0075(7) 0.032(2) Uani d . 1 . .
H H18A 0.5809 0.3798 0.9746 0.048 Uiso calc R 1 . .
H H18B 0.7088 0.3198 0.9946 0.048 Uiso calc R 1 . .
H H18C 0.6366 0.3142 1.0770 0.048 Uiso calc R 1 . .
O O18 0.4780(4) 0.1528(5) 1.0074(4) 0.0214(14) Uani d . 1 . .
C C19 0.9460(7) 0.2132(8) 0.9097(6) 0.025(2) Uani d . 1 . .
H H19A 1.0197 0.2303 0.8920 0.038 Uiso calc R 1 . .
H H19B 0.9595 0.1946 0.9789 0.038 Uiso calc R 1 . .
H H19C 0.8965 0.2932 0.8943 0.038 Uiso calc R 1 . .
C C1A 1.0080(6) 0.6562(8) 0.5599(6) 0.0179(19) Uani d . 1 . .
H H1C 0.9721 0.6734 0.4914 0.022 Uiso calc R 1 . .
H H1D 1.0204 0.7453 0.5927 0.022 Uiso calc R 1 . .
C C2A 1.1250(6) 0.5893(8) 0.5655(6) 0.019(2) Uani d . 1 . .
H H2C 1.1147 0.5052 0.5265 0.023 Uiso calc R 1 . .
H H2D 1.1748 0.6514 0.5382 0.023 Uiso calc R 1 . .
C C3A 1.1829(6) 0.5553(9) 0.6679(6) 0.023(2) Uani d . 1 . .
H H3A 1.1985 0.6426 0.7042 0.027 Uiso calc R 1 . .
O O3A 1.2915(4) 0.4876(5) 0.6748(4) 0.0249(15) Uani d . 1 . .
H H31A 1.2807 0.4129 0.6458 0.037 Uiso calc R 1 . .
C C4A 1.1040(6) 0.4710(8) 0.7157(6) 0.0159(19) Uani d . 1 . .
H H4C 1.0966 0.3790 0.6872 0.019 Uiso calc R 1 . .
H H4D 1.1397 0.4617 0.7850 0.019 Uiso calc R 1 . .
C C5A 0.9847(6) 0.5318(7) 0.7051(6) 0.018(2) Uani d . 1 . .
C C6A 0.9427(7) 0.5484(8) 0.7832(6) 0.022(2) Uani d . 1 . .
H H6A 0.9910 0.5259 0.8435 0.026 Uiso calc R 1 . .
C C7A 0.8240(6) 0.6003(8) 0.7828(6) 0.021(2) Uani d . 1 . .
H H7C 0.8299 0.6927 0.8107 0.025 Uiso calc R 1 . .
H H7D 0.7879 0.5410 0.8240 0.025 Uiso calc R 1 . .
C C8A 0.7465(6) 0.6047(8) 0.6807(6) 0.017(2) Uani d . 1 . .
H H8A 0.7197 0.5105 0.6617 0.021 Uiso calc R 1 . .
C C9A 0.8139(6) 0.6586(8) 0.6069(5) 0.0151(19) Uani d . 1 . .
H H9A 0.8412 0.7519 0.6281 0.018 Uiso calc R 1 . .
C C10A 0.9220(6) 0.5721(8) 0.6053(6) 0.0154(19) Uani d . 1 . .
O O11A 0.7782(4) 0.7336(5) 0.4348(4) 0.0206(13) Uani d . 1 . .
H H112 0.7982 0.6734 0.3932 0.031 Uiso d . 1 . .
C C11A 0.7297(6) 0.6732(8) 0.5095(6) 0.023(2) Uani d . 1 . .
H H11A 0.6993 0.5812 0.4875 0.028 Uiso calc R 1 . .
C C12A 0.6271(7) 0.7661(8) 0.5166(6) 0.020(2) Uani d . 1 . .
H H12C 0.6559 0.8577 0.5381 0.024 Uiso calc R 1 . .
H H12D 0.5751 0.7749 0.4524 0.024 Uiso calc R 1 . .
C C13A 0.5615(6) 0.7080(8) 0.5867(6) 0.0151(19) Uani d . 1 . .
C C14A 0.6422(6) 0.6918(8) 0.6842(6) 0.0163(19) Uani d . 1 . .
H H14A 0.6714 0.7844 0.7056 0.020 Uiso calc R 1 . .
C C15A 0.5714(6) 0.6418(8) 0.7560(6) 0.019(2) Uani d . 1 . .
H H15C 0.5430 0.5489 0.7381 0.023 Uiso calc R 1 . .
H H15D 0.6216 0.6378 0.8213 0.023 Uiso calc R 1 . .
C C16A 0.4701(7) 0.7344(9) 0.7573(6) 0.026(2) Uani d . 1 . .
H H16C 0.4069 0.6782 0.7715 0.031 Uiso calc R 1 . .
H H16D 0.4933 0.7989 0.8113 0.031 Uiso calc R 1 . .
C C17A 0.4230(7) 0.8149(9) 0.6678(7) 0.026(2) Uani d . 1 . .
O O17A 0.3402(5) 0.8891(6) 0.6618(5) 0.0392(18) Uani d . 1 . .
C C18A 0.4953(6) 0.5794(9) 0.5487(6) 0.027(2) Uani d . 1 . .
H H18D 0.4460 0.5977 0.4853 0.041 Uiso calc R 1 . .
H H18E 0.4477 0.5512 0.5933 0.041 Uiso calc R 1 . .
H H18F 0.5498 0.5070 0.5431 0.041 Uiso calc R 1 . .
O O18A 0.4727(4) 0.8118(6) 0.5927(4) 0.0279(16) Uani d . 1 . .
C C19A 0.8888(7) 0.4390(8) 0.5463(6) 0.021(2) Uani d . 1 . .
H H19D 0.8344 0.3868 0.5744 0.031 Uiso calc R 1 . .
H H19E 0.9581 0.3847 0.5479 0.031 Uiso calc R 1 . .
H H19F 0.8531 0.4621 0.4795 0.031 Uiso calc R 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 0.0000 '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 0.0000 '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
C10 C1 C2 . . 113.4(7) ?
C10 C1 H1A . . 108.9 ?
C2 C1 H1A . . 108.9 ?
C10 C1 H1B . . 108.9 ?
C2 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
C3 C2 C1 . . 111.2(7) ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
O3 C3 C2 . . 112.6(7) ?
O3 C3 C4 . . 106.2(6) ?
C2 C3 C4 . . 111.7(7) ?
O3 C3 H3 . . 108.8 ?
C2 C3 H3 . . 108.8 ?
C4 C3 H3 . . 108.8 ?
C3 O3 H31 . . 109.5 ?
C3 C4 C5 . . 113.6(7) ?
C3 C4 H4A . . 108.9 ?
C5 C4 H4A . . 108.9 ?
C3 C4 H4B . . 108.9 ?
C5 C4 H4B . . 108.9 ?
H4A C4 H4B . . 107.7 ?
C6 C5 C4 . . 120.4(8) ?
C6 C5 C10 . . 124.0(7) ?
C4 C5 C10 . . 115.5(7) ?
C5 C6 C7 . . 125.2(9) ?
C5 C6 H6 . . 117.4 ?
C7 C6 H6 . . 117.4 ?
C6 C7 C8 . . 110.6(7) ?
C6 C7 H7A . . 109.5 ?
C8 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.1 ?
C7 C8 C14 . . 111.4(6) ?
C7 C8 C9 . . 109.0(6) ?
C14 C8 C9 . . 112.8(6) ?
C7 C8 H8 . . 107.8 ?
C14 C8 H8 . . 107.8 ?
C9 C8 H8 . . 107.8 ?
C11 C9 C8 . . 113.8(6) ?
C11 C9 C10 . . 113.1(6) ?
C8 C9 C10 . . 110.1(6) ?
C11 C9 H9 . . 106.4 ?
C8 C9 H9 . . 106.4 ?
C10 C9 H9 . . 106.4 ?
C5 C10 C19 . . 110.0(6) ?
C5 C10 C1 . . 106.4(7) ?
C19 C10 C1 . . 109.5(6) ?
C5 C10 C9 . . 110.2(6) ?
C19 C10 C9 . . 110.1(6) ?
C1 C10 C9 . . 110.7(6) ?
O11 C11 C9 . . 112.8(6) ?
O11 C11 C12 . . 108.2(6) ?
C9 C11 C12 . . 113.8(7) ?
O11 C11 H11 . . 107.2 ?
C9 C11 H11 . . 107.2 ?
C12 C11 H11 . . 107.2 ?
C11 O11 H111 . . 109.5 ?
C13 C12 C11 . . 112.2(7) ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12B . . 109.2 ?
C11 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
O18 C13 C14 . . 112.1(6) ?
O18 C13 C12 . . 104.1(6) ?
C14 C13 C12 . . 109.1(7) ?
O18 C13 C18 . . 105.1(6) ?
C14 C13 C18 . . 114.5(7) ?
C12 C13 C18 . . 111.5(7) ?
C13 C14 C15 . . 110.9(7) ?
C13 C14 C8 . . 111.3(6) ?
C15 C14 C8 . . 114.1(6) ?
C13 C14 H14 . . 106.7 ?
C15 C14 H14 . . 106.7 ?
C8 C14 H14 . . 106.7 ?
C16 C15 C14 . . 109.7(7) ?
C16 C15 H15A . . 109.7 ?
C14 C15 H15A . . 109.7 ?
C16 C15 H15B . . 109.7 ?
C14 C15 H15B . . 109.7 ?
H15A C15 H15B . . 108.2 ?
C17 C16 C15 . . 117.9(7) ?
C17 C16 H16A . . 107.8 ?
C15 C16 H16A . . 107.8 ?
C17 C16 H16B . . 107.8 ?
C15 C16 H16B . . 107.8 ?
H16A C16 H16B . . 107.2 ?
O17 C17 O18 . . 115.4(8) ?
O17 C17 C16 . . 124.3(7) ?
O18 C17 C16 . . 120.3(7) ?
C13 C18 H18A . . 109.5 ?
C13 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C13 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 O18 C13 . . 120.8(6) ?
C10 C19 H19A . . 109.5 ?
C10 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C10 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C2A C1A C10A . . 115.0(7) ?
C2A C1A H1C . . 108.5 ?
C10A C1A H1C . . 108.5 ?
C2A C1A H1D . . 108.5 ?
C10A C1A H1D . . 108.5 ?
H1C C1A H1D . . 107.5 ?
C3A C2A C1A . . 111.4(6) ?
C3A C2A H2C . . 109.3 ?
C1A C2A H2C . . 109.3 ?
C3A C2A H2D . . 109.3 ?
C1A C2A H2D . . 109.3 ?
H2C C2A H2D . . 108.0 ?
O3A C3A C2A . . 112.5(6) ?
O3A C3A C4A . . 110.6(7) ?
C2A C3A C4A . . 110.9(6) ?
O3A C3A H3A . . 107.6 ?
C2A C3A H3A . . 107.6 ?
C4A C3A H3A . . 107.6 ?
C3A O3A H31A . . 109.5 ?
C5A C4A C3A . . 113.4(6) ?
C5A C4A H4C . . 108.9 ?
C3A C4A H4C . . 108.9 ?
C5A C4A H4D . . 108.9 ?
C3A C4A H4D . . 108.9 ?
H4C C4A H4D . . 107.7 ?
C6A C5A C10A . . 124.0(7) ?
C6A C5A C4A . . 118.9(8) ?
C10A C5A C4A . . 117.2(7) ?
C5A C6A C7A . . 124.5(8) ?
C5A C6A H6A . . 117.7 ?
C7A C6A H6A . . 117.7 ?
C6A C7A C8A . . 112.4(7) ?
C6A C7A H7C . . 109.1 ?
C8A C7A H7C . . 109.1 ?
C6A C7A H7D . . 109.1 ?
C8A C7A H7D . . 109.1 ?
H7C C7A H7D . . 107.9 ?
C14A C8A C7A . . 108.1(6) ?
C14A C8A C9A . . 112.2(6) ?
C7A C8A C9A . . 111.0(6) ?
C14A C8A H8A . . 108.5 ?
C7A C8A H8A . . 108.5 ?
C9A C8A H8A . . 108.5 ?
C11A C9A C8A . . 108.3(6) ?
C11A C9A C10A . . 114.8(6) ?
C8A C9A C10A . . 112.2(6) ?
C11A C9A H9A . . 107.1 ?
C8A C9A H9A . . 107.1 ?
C10A C9A H9A . . 107.1 ?
C5A C10A C9A . . 111.9(6) ?
C5A C10A C19A . . 107.6(6) ?
C9A C10A C19A . . 110.9(6) ?
C5A C10A C1A . . 107.2(6) ?
C9A C10A C1A . . 109.7(6) ?
C19A C10A C1A . . 109.5(6) ?
C11A O11A H112 . . 114.6 ?
O11A C11A C9A . . 114.7(6) ?
O11A C11A C12A . . 104.6(6) ?
C9A C11A C12A . . 111.4(6) ?
O11A C11A H11A . . 108.6 ?
C9A C11A H11A . . 108.6 ?
C12A C11A H11A . . 108.6 ?
C13A C12A C11A . . 110.5(6) ?
C13A C12A H12C . . 109.6 ?
C11A C12A H12C . . 109.6 ?
C13A C12A H12D . . 109.6 ?
C11A C12A H12D . . 109.6 ?
H12C C12A H12D . . 108.1 ?
O18A C13A C12A . . 104.8(6) ?
O18A C13A C14A . . 109.7(6) ?
C12A C13A C14A . . 109.3(6) ?
O18A C13A C18A . . 105.8(6) ?
C12A C13A C18A . . 112.4(7) ?
C14A C13A C18A . . 114.3(7) ?
C13A C14A C8A . . 112.9(6) ?
C13A C14A C15A . . 108.2(6) ?
C8A C14A C15A . . 114.2(7) ?
C13A C14A H14A . . 107.0 ?
C8A C14A H14A . . 107.0 ?
C15A C14A H14A . . 107.0 ?
C16A C15A C14A . . 111.6(7) ?
C16A C15A H15C . . 109.3 ?
C14A C15A H15C . . 109.3 ?
C16A C15A H15D . . 109.3 ?
C14A C15A H15D . . 109.3 ?
H15C C15A H15D . . 108.0 ?
C17A C16A C15A . . 117.2(7) ?
C17A C16A H16C . . 108.0 ?
C15A C16A H16C . . 108.0 ?
C17A C16A H16D . . 108.0 ?
C15A C16A H16D . . 108.0 ?
H16C C16A H16D . . 107.2 ?
O17A C17A O18A . . 117.0(9) ?
O17A C17A C16A . . 121.6(8) ?
O18A C17A C16A . . 121.4(7) ?
C13A C18A H18D . . 109.5 ?
C13A C18A H18E . . 109.5 ?
H18D C18A H18E . . 109.5 ?
C13A C18A H18F . . 109.5 ?
H18D C18A H18F . . 109.5 ?
H18E C18A H18F . . 109.5 ?
C17A O18A C13A . . 120.6(6) ?
C10A C19A H19D . . 109.5 ?
C10A C19A H19E . . 109.5 ?
H19D C19A H19E . . 109.5 ?
C10A C19A H19F . . 109.5 ?
H19D C19A H19F . . 109.5 ?
H19E C19A H19F . . 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
C1 C10 . 1.545(10) ?
C1 C2 . 1.554(10) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.474(12) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 O3 . 1.447(9) ?
C3 C4 . 1.509(11) ?
C3 H3 . 1.0000 ?
O3 H31 . 0.8400 ?
C4 C5 . 1.512(10) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.298(12) ?
C5 C10 . 1.522(12) ?
C6 C7 . 1.516(10) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.526(10) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C14 . 1.542(10) ?
C8 C9 . 1.560(10) ?
C8 H8 . 1.0000 ?
C9 C11 . 1.516(11) ?
C9 C10 . 1.574(9) ?
C9 H9 . 1.0000 ?
C10 C19 . 1.543(10) ?
C11 O11 . 1.427(9) ?
C11 C12 . 1.535(10) ?
C11 H11 . 1.0000 ?
O11 H111 . 0.8400 ?
C12 C13 . 1.520(11) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 O18 . 1.477(8) ?
C13 C14 . 1.494(11) ?
C13 C18 . 1.531(12) ?
C14 C15 . 1.524(11) ?
C14 H14 . 1.0000 ?
C15 C16 . 1.516(10) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.484(11) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 O17 . 1.230(9) ?
C17 O18 . 1.356(9) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C1A C2A . 1.528(10) ?
C1A C10A . 1.564(10) ?
C1A H1C . 0.9900 ?
C1A H1D . 0.9900 ?
C2A C3A . 1.509(11) ?
C2A H2C . 0.9900 ?
C2A H2D . 0.9900 ?
C3A O3A . 1.440(8) ?
C3A C4A . 1.522(10) ?
C3A H3A . 1.0000 ?
O3A H31A . 0.8400 ?
C4A C5A . 1.519(10) ?
C4A H4C . 0.9900 ?
C4A H4D . 0.9900 ?
C5A C6A . 1.325(10) ?
C5A C10A . 1.508(11) ?
C6A C7A . 1.503(10) ?
C6A H6A . 0.9500 ?
C7A C8A . 1.543(11) ?
C7A H7C . 0.9900 ?
C7A H7D . 0.9900 ?
C8A C14A . 1.521(10) ?
C8A C9A . 1.549(10) ?
C8A H8A . 1.0000 ?
C9A C11A . 1.530(11) ?
C9A C10A . 1.549(10) ?
C9A H9A . 1.0000 ?
C10A C19A . 1.561(10) ?
O11A C11A . 1.446(9) ?
O11A H112 . 0.9069 ?
C11A C12A . 1.549(10) ?
C11A H11A . 1.0000 ?
C12A C13A . 1.510(10) ?
C12A H12C . 0.9900 ?
C12A H12D . 0.9900 ?
C13A O18A . 1.487(9) ?
C13A C14A . 1.514(10) ?
C13A C18A . 1.528(11) ?
C14A C15A . 1.543(10) ?
C14A H14A . 1.0000 ?
C15A C16A . 1.517(10) ?
C15A H15C . 0.9900 ?
C15A H15D . 0.9900 ?
C16A C17A . 1.503(12) ?
C16A H16C . 0.9900 ?
C16A H16D . 0.9900 ?
C17A O17A . 1.216(9) ?
C17A O18A . 1.331(10) ?
C18A H18D . 0.9800 ?
C18A H18E . 0.9800 ?
C18A H18F . 0.9800 ?
C19A H19D . 0.9800 ?
C19A H19E . 0.9800 ?
C19A H19F . 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
O3 H31 O17A 1_645 0.84 2.04 2.773(8) 145
O11 H111 O17 2_647 0.84 2.02 2.861(8) 180
O3A H31A O11A 2_746 0.84 2.14 2.970(8) 170
O11A H112 O3 2_756 0.91 2.01 2.918(8) 179
C16 H16B O3 1_455 0.99 2.47 3.418(10) 161
C18A H18E O3A 1_455 0.98 2.48 3.443(9) 167
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 . . . . -57.8(10) ?
C1 C2 C3 O3 . . . . 172.5(6) ?
C1 C2 C3 C4 . . . . 53.2(9) ?
O3 C3 C4 C5 . . . . -173.8(7) ?
C2 C3 C4 C5 . . . . -50.7(10) ?
C3 C4 C5 C6 . . . . -126.5(10) ?
C3 C4 C5 C10 . . . . 51.8(10) ?
C4 C5 C6 C7 . . . . -172.1(7) ?
C10 C5 C6 C7 . . . . 9.7(15) ?
C5 C6 C7 C8 . . . . 12.2(12) ?
C6 C7 C8 C14 . . . . -172.9(7) ?
C6 C7 C8 C9 . . . . -47.9(9) ?
C7 C8 C9 C11 . . . . -167.3(7) ?
C14 C8 C9 C11 . . . . -43.0(9) ?
C7 C8 C9 C10 . . . . 64.6(8) ?
C14 C8 C9 C10 . . . . -171.2(7) ?
C6 C5 C10 C19 . . . . -115.1(9) ?
C4 C5 C10 C19 . . . . 66.7(8) ?
C6 C5 C10 C1 . . . . 126.5(9) ?
C4 C5 C10 C1 . . . . -51.7(8) ?
C6 C5 C10 C9 . . . . 6.5(11) ?
C4 C5 C10 C9 . . . . -171.7(6) ?
C2 C1 C10 C5 . . . . 54.3(9) ?
C2 C1 C10 C19 . . . . -64.5(9) ?
C2 C1 C10 C9 . . . . 174.0(7) ?
C11 C9 C10 C5 . . . . -171.1(7) ?
C8 C9 C10 C5 . . . . -42.6(8) ?
C11 C9 C10 C19 . . . . -49.6(9) ?
C8 C9 C10 C19 . . . . 79.0(8) ?
C11 C9 C10 C1 . . . . 71.6(9) ?
C8 C9 C10 C1 . . . . -159.9(7) ?
C8 C9 C11 O11 . . . . 165.7(6) ?
C10 C9 C11 O11 . . . . -67.7(8) ?
C8 C9 C11 C12 . . . . 41.9(9) ?
C10 C9 C11 C12 . . . . 168.4(6) ?
O11 C11 C12 C13 . . . . -177.2(7) ?
C9 C11 C12 C13 . . . . -50.9(10) ?
C11 C12 C13 O18 . . . . -179.8(7) ?
C11 C12 C13 C14 . . . . 60.3(9) ?
C11 C12 C13 C18 . . . . -67.0(9) ?
O18 C13 C14 C15 . . . . 55.6(8) ?
C12 C13 C14 C15 . . . . 170.3(6) ?
C18 C13 C14 C15 . . . . -64.1(8) ?
O18 C13 C14 C8 . . . . -176.2(6) ?
C12 C13 C14 C8 . . . . -61.5(8) ?
C18 C13 C14 C8 . . . . 64.1(8) ?
C7 C8 C14 C13 . . . . 176.3(7) ?
C9 C8 C14 C13 . . . . 53.4(8) ?
C7 C8 C14 C15 . . . . -57.3(9) ?
C9 C8 C14 C15 . . . . 179.8(7) ?
C13 C14 C15 C16 . . . . -55.1(9) ?
C8 C14 C15 C16 . . . . 178.3(7) ?
C14 C15 C16 C17 . . . . 35.3(11) ?
C15 C16 C17 O17 . . . . 166.5(8) ?
C15 C16 C17 O18 . . . . -15.8(11) ?
O17 C17 O18 C13 . . . . -166.7(7) ?
C16 C17 O18 C13 . . . . 15.4(11) ?
C14 C13 O18 C17 . . . . -35.6(9) ?
C12 C13 O18 C17 . . . . -153.4(7) ?
C18 C13 O18 C17 . . . . 89.3(8) ?
C10A C1A C2A C3A . . . . -56.1(9) ?
C1A C2A C3A O3A . . . . 177.9(7) ?
C1A C2A C3A C4A . . . . 53.5(9) ?
O3A C3A C4A C5A . . . . -176.0(7) ?
C2A C3A C4A C5A . . . . -50.5(9) ?
C3A C4A C5A C6A . . . . -128.5(8) ?
C3A C4A C5A C10A . . . . 50.5(9) ?
C10A C5A C6A C7A . . . . 4.5(12) ?
C4A C5A C6A C7A . . . . -176.7(7) ?
C5A C6A C7A C8A . . . . 11.9(11) ?
C6A C7A C8A C14A . . . . -165.1(6) ?
C6A C7A C8A C9A . . . . -41.8(9) ?
C14A C8A C9A C11A . . . . -53.8(8) ?
C7A C8A C9A C11A . . . . -174.7(6) ?
C14A C8A C9A C10A . . . . 178.5(7) ?
C7A C8A C9A C10A . . . . 57.5(8) ?
C6A C5A C10A C9A . . . . 10.6(10) ?
C4A C5A C10A C9A . . . . -168.3(7) ?
C6A C5A C10A C19A . . . . -111.4(8) ?
C4A C5A C10A C19A . . . . 69.7(8) ?
C6A C5A C10A C1A . . . . 130.9(8) ?
C4A C5A C10A C1A . . . . -48.0(8) ?
C11A C9A C10A C5A . . . . -165.2(6) ?
C8A C9A C10A C5A . . . . -41.1(8) ?
C11A C9A C10A C19A . . . . -45.2(9) ?
C8A C9A C10A C19A . . . . 79.0(8) ?
C11A C9A C10A C1A . . . . 75.9(8) ?
C8A C9A C10A C1A . . . . -159.9(6) ?
C2A C1A C10A C5A . . . . 50.9(9) ?
C2A C1A C10A C9A . . . . 172.6(7) ?
C2A C1A C10A C19A . . . . -65.5(9) ?
C8A C9A C11A O11A . . . . 175.0(6) ?
C10A C9A C11A O11A . . . . -58.8(9) ?
C8A C9A C11A C12A . . . . 56.3(8) ?
C10A C9A C11A C12A . . . . -177.5(6) ?
O11A C11A C12A C13A . . . . 175.2(6) ?
C9A C11A C12A C13A . . . . -60.3(8) ?
C11A C12A C13A O18A . . . . 175.4(6) ?
C11A C12A C13A C14A . . . . 57.9(8) ?
C11A C12A C13A C18A . . . . -70.2(8) ?
O18A C13A C14A C8A . . . . -170.7(6) ?
C12A C13A C14A C8A . . . . -56.4(8) ?
C18A C13A C14A C8A . . . . 70.7(8) ?
O18A C13A C14A C15A . . . . 61.8(8) ?
C12A C13A C14A C15A . . . . 176.2(6) ?
C18A C13A C14A C15A . . . . -56.8(8) ?
C7A C8A C14A C13A . . . . 177.9(6) ?
C9A C8A C14A C13A . . . . 55.3(8) ?
C7A C8A C14A C15A . . . . -57.9(8) ?
C9A C8A C14A C15A . . . . 179.5(6) ?
C13A C14A C15A C16A . . . . -54.4(8) ?
C8A C14A C15A C16A . . . . 178.9(7) ?
C14A C15A C16A C17A . . . . 25.9(10) ?
C15A C16A C17A O17A . . . . 178.2(8) ?
C15A C16A C17A O18A . . . . -4.2(12) ?
O17A C17A O18A C13A . . . . -169.8(7) ?
C16A C17A O18A C13A . . . . 12.5(11) ?
C12A C13A O18A C17A . . . . -159.4(7) ?
C14A C13A O18A C17A . . . . -42.2(9) ?
C18A C13A O18A C17A . . . . 81.6(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079448
