#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/93/2009343.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_2009343
loop_
_publ_author_name
'Andrade, L. C. R.'
'Paixão, J. A.'
'de Almeida, M. J.'
'Tavares da Silva, E. J.'
'Sá e Melo, M. L.'
'Campos Neves, A. S.'
_publ_section_title
;
 3α-Hydroxy-5α-androstane-4,17-dione
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2149
_journal_page_last               2151
_journal_paper_doi               10.1107/S0108270199011877
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C19 H28 O3'
_chemical_formula_sum            'C19 H28 O3'
_chemical_formula_weight         304.43
_chemical_name_systematic
;
 3α-Hydroxy-5α-androstane-4,17-dione
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.21(3)
_cell_angle_beta                 85.78(3)
_cell_angle_gamma                84.60(3)
_cell_formula_units_Z            2
_cell_length_a                   7.869(2)
_cell_length_b                   10.113(3)
_cell_length_c                   10.771(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.43
_cell_measurement_theta_min      8.92
_cell_volume                     827.6(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'profile data from ω-2θ'
_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  0.016
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4431
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         4.99
_diffrn_standards_decay_%        1.3
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.096
_refine_ls_R_factor_gt           0.039
_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)+(0.0577P)²+0.0792P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                2741
_reflns_number_total             4377
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1300.cif
_cod_data_source_block           and23
_cod_database_code               2009343
_cod_database_fobs_code          2009343
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_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
_atom_site_type_symbol
C1 0.9786(4) 0.9721(3) 0.8636(3) 0.0512(8) Uani d . 1 . . C
H1 1.0677 0.9668 0.7975 0.077 Uiso calc R 1 . . H
H2 0.9322 1.0665 0.8502 0.077 Uiso calc R 1 . . H
C2 1.0571(4) 0.9285(4) 0.9952(3) 0.0571(8) Uani d . 1 . . C
H3 1.1156 0.8381 1.0044 0.086 Uiso calc R 1 . . H
H4 1.1413 0.9912 0.9997 0.086 Uiso calc R 1 . . H
C3 0.9250(4) 0.9264(3) 1.1042(3) 0.0570(8) Uani d . 1 . . C
H5 0.9772 0.8856 1.1858 0.086 Uiso calc R 1 . . H
C4 0.7824(4) 0.8426(3) 1.0868(3) 0.0508(7) Uani d . 1 . . C
C5 0.6984(4) 0.8912(3) 0.9613(3) 0.0461(7) Uani d . 1 . . C
H6 0.6607 0.9880 0.9529 0.069 Uiso calc R 1 . . H
C6 0.5412(4) 0.8175(3) 0.9553(3) 0.0514(7) Uani d . 1 . . C
H7 0.4589 0.8300 1.0239 0.077 Uiso calc R 1 . . H
H8 0.5729 0.7205 0.9668 0.077 Uiso calc R 1 . . H
C7 0.4609(4) 0.8721(3) 0.8276(3) 0.0511(8) Uani d . 1 . . C
H9 0.4177 0.9665 0.8207 0.077 Uiso calc R 1 . . H
H10 0.3650 0.8199 0.8235 0.077 Uiso calc R 1 . . H
C8 0.5890(3) 0.8637(3) 0.7156(3) 0.0452(7) Uani d . 1 . . C
H11 0.6263 0.7671 0.7219 0.068 Uiso calc R 1 . . H
C9 0.7476(3) 0.9390(3) 0.7222(3) 0.0453(7) Uani d . 1 . . C
H12 0.7059 1.0336 0.7212 0.068 Uiso calc R 1 . . H
C10 0.8361(3) 0.8828(3) 0.8509(3) 0.0424(7) Uani d . 1 . . C
C11 0.8722(4) 0.9455(3) 0.6039(3) 0.0536(8) Uani d . 1 . . C
H13 0.9580 1.0076 0.6062 0.080 Uiso calc R 1 . . H
H14 0.9303 0.8556 0.6086 0.080 Uiso calc R 1 . . H
C12 0.7855(4) 0.9925(4) 0.4758(3) 0.0573(8) Uani d . 1 . . C
H15 0.7432 1.0877 0.4635 0.086 Uiso calc R 1 . . H
H16 0.8681 0.9842 0.4062 0.086 Uiso calc R 1 . . H
C13 0.6381(4) 0.9062(3) 0.4745(3) 0.0502(7) Uani d . 1 . . C
C14 0.5109(3) 0.9194(3) 0.5872(3) 0.0483(7) Uani d . 1 . . C
H17 0.4831 1.0174 0.5799 0.073 Uiso calc R 1 . . H
C15 0.3490(4) 0.8622(4) 0.5582(3) 0.0637(9) Uani d . 1 . . C
H18 0.2487 0.8981 0.6011 0.095 Uiso calc R 1 . . H
H19 0.3570 0.7633 0.5841 0.095 Uiso calc R 1 . . H
C16 0.3433(5) 0.9122(4) 0.4118(4) 0.0727(10) Uani d . 1 . . C
H20 0.3128 0.8400 0.3744 0.109 Uiso calc R 1 . . H
H21 0.2600 0.9899 0.3894 0.109 Uiso calc R 1 . . H
C17 0.5207(4) 0.9523(3) 0.3645(3) 0.0569(8) Uani d . 1 . . C
C18 0.6986(5) 0.7567(4) 0.4748(3) 0.0626(9) Uani d . 1 . . C
H22 0.6010 0.7050 0.4794 0.094 Uiso calc R 1 . . H
H23 0.7659 0.7183 0.5474 0.094 Uiso calc R 1 . . H
H24 0.7665 0.7535 0.3976 0.094 Uiso calc R 1 . . H
C19 0.9130(4) 0.7345(3) 0.8611(3) 0.0521(7) Uani d . 1 . . C
H25 1.0177 0.7351 0.8094 0.078 Uiso calc R 1 . . H
H26 0.8335 0.6839 0.8317 0.078 Uiso calc R 1 . . H
H27 0.9356 0.6926 0.9487 0.078 Uiso calc R 1 . . H
O3 0.8607(3) 1.0639(2) 1.1013(2) 0.0711(7) Uani d . 1 . . O
H28 0.7830 1.0642 1.1563 0.107 Uiso calc R 1 . . H
O4 0.7483(3) 0.7392(2) 1.1648(2) 0.0672(6) Uani d . 1 . . O
O17 0.5593(3) 1.0146(3) 0.2567(2) 0.0717(7) Uani d . 1 . . O
C1' 0.0486(4) 0.3164(4) 0.3535(3) 0.0640(9) Uani d . 1 . . C
H1' -0.0403 0.3243 0.2937 0.096 Uiso calc R 1 . . H
H2' 0.0910 0.2211 0.3772 0.096 Uiso calc R 1 . . H
C2' -0.0296(5) 0.3597(5) 0.4732(4) 0.0789(11) Uani d . 1 . . C
H3' -0.0857 0.4510 0.4487 0.118 Uiso calc R 1 . . H
H4' -0.1153 0.2982 0.5142 0.118 Uiso calc R 1 . . H
C3' 0.1052(6) 0.3580(4) 0.5671(4) 0.0754(11) Uani d . 1 . . C
H5' 0.0548 0.3985 0.6368 0.113 Uiso calc R 1 . . H
C4' 0.2490(5) 0.4406(4) 0.4973(3) 0.0666(10) Uani d . 1 . . C
C5' 0.3331(4) 0.3903(3) 0.3855(3) 0.0555(8) Uani d . 1 . . C
H6' 0.3674 0.2930 0.4168 0.083 Uiso calc R 1 . . H
C6' 0.4936(5) 0.4599(4) 0.3290(4) 0.0707(10) Uani d . 1 . . C
H7' 0.4651 0.5573 0.2991 0.106 Uiso calc R 1 . . H
H8' 0.5755 0.4468 0.3947 0.106 Uiso calc R 1 . . H
C7' 0.5729(4) 0.4024(4) 0.2187(3) 0.0655(10) Uani d . 1 . . C
H9' 0.6140 0.3077 0.2507 0.098 Uiso calc R 1 . . H
H10' 0.6701 0.4527 0.1804 0.098 Uiso calc R 1 . . H
C8' 0.4456(4) 0.4109(3) 0.1173(3) 0.0501(7) Uani d . 1 . . C
H11' 0.4124 0.5077 0.0818 0.075 Uiso calc R 1 . . H
C9' 0.2824(4) 0.3405(3) 0.1757(3) 0.0484(7) Uani d . 1 . . C
H12' 0.3202 0.2455 0.2148 0.073 Uiso calc R 1 . . H
C10' 0.1960(4) 0.4014(3) 0.2855(3) 0.0523(8) Uani d . 1 . . C
C11' 0.1567(4) 0.3347(4) 0.0740(3) 0.0630(9) Uani d . 1 . . C
H13' 0.0676 0.2761 0.1141 0.094 Uiso calc R 1 . . H
H14' 0.1029 0.4256 0.0417 0.094 Uiso calc R 1 . . H
C12' 0.2437(4) 0.2811(4) -0.0388(4) 0.0671(9) Uani d . 1 . . C
H15' 0.2817 0.1854 -0.0094 0.101 Uiso calc R 1 . . H
H16' 0.1619 0.2887 -0.1037 0.101 Uiso calc R 1 . . H
C13' 0.3950(4) 0.3608(3) -0.0964(3) 0.0524(8) Uani d . 1 . . C
C14' 0.5200(4) 0.3487(3) 0.0078(3) 0.0545(8) Uani d . 1 . . C
H17' 0.5434 0.2508 0.0445 0.082 Uiso calc R 1 . . H
C15' 0.6844(5) 0.3982(4) -0.0657(4) 0.0711(10) Uani d . 1 . . C
H18' 0.7836 0.3605 -0.0168 0.107 Uiso calc R 1 . . H
H19' 0.6817 0.4971 -0.0859 0.107 Uiso calc R 1 . . H
C16' 0.6873(5) 0.3450(4) -0.1878(4) 0.0811(11) Uani d . 1 . . C
H20' 0.7206 0.4147 -0.2621 0.122 Uiso calc R 1 . . H
H21' 0.7673 0.2651 -0.1823 0.122 Uiso calc R 1 . . H
C17' 0.5084(5) 0.3095(3) -0.1968(4) 0.0653(9) Uani d . 1 . . C
C18' 0.3390(5) 0.5104(3) -0.1610(3) 0.0653(9) Uani d . 1 . . C
H22' 0.4373 0.5564 -0.2007 0.098 Uiso calc R 1 . . H
H23' 0.2855 0.5557 -0.0978 0.098 Uiso calc R 1 . . H
H24' 0.2593 0.5120 -0.2248 0.098 Uiso calc R 1 . . H
C19' 0.1268(5) 0.5510(4) 0.2361(4) 0.0717(10) Uani d . 1 . . C
H25' 0.0990 0.5924 0.3073 0.107 Uiso calc R 1 . . H
H26' 0.0261 0.5539 0.1901 0.107 Uiso calc R 1 . . H
H27' 0.2123 0.6001 0.1802 0.107 Uiso calc R 1 . . H
O3' 0.1644(4) 0.2204(3) 0.6173(3) 0.0910(9) Uani d . 1 . . O
H28' 0.2502 0.2179 0.6569 0.137 Uiso calc R 1 . . H
O4' 0.2836(5) 0.5437(3) 0.5248(3) 0.0975(10) Uani d . 1 . . O
O17' 0.4652(4) 0.2502(3) -0.2739(3) 0.0855(8) Uani d . 1 . . O
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 112.6(2) ?
C2 C1 H1 109.1 ?
C10 C1 H1 109.1 ?
C2 C1 H2 109.1 ?
C10 C1 H2 109.1 ?
H1 C1 H2 107.8 ?
C3 C2 C1 112.5(3) ?
C3 C2 H3 109.1 ?
C1 C2 H3 109.1 ?
C3 C2 H4 109.1 ?
C1 C2 H4 109.1 ?
H3 C2 H4 107.8 ?
O3 C3 C2 108.2(3) ?
O3 C3 C4 110.5(3) ?
C2 C3 C4 108.7(3) yes
O3 C3 H5 109.8 ?
C2 C3 H5 109.8 ?
C4 C3 H5 109.8 ?
O4 C4 C5 123.3(3) ?
O4 C4 C3 121.9(3) ?
C5 C4 C3 114.6(3) yes
C4 C5 C6 112.9(3) ?
C4 C5 C10 108.5(2) ?
C6 C5 C10 113.6(2) ?
C4 C5 H6 107.2 ?
C6 C5 H6 107.2 ?
C10 C5 H6 107.2 ?
C5 C6 C7 110.5(2) ?
C5 C6 H7 109.6 ?
C7 C6 H7 109.6 ?
C5 C6 H8 109.6 ?
C7 C6 H8 109.6 ?
H7 C6 H8 108.1 ?
C6 C7 C8 111.7(2) ?
C6 C7 H9 109.3 ?
C8 C7 H9 109.3 ?
C6 C7 H10 109.3 ?
C8 C7 H10 109.3 ?
H9 C7 H10 107.9 ?
C14 C8 C7 112.3(2) ?
C14 C8 C9 109.8(2) ?
C7 C8 C9 111.0(2) ?
C14 C8 H11 107.9 ?
C7 C8 H11 107.9 ?
C9 C8 H11 107.9 ?
C8 C9 C11 112.7(2) ?
C8 C9 C10 111.9(2) ?
C11 C9 C10 113.1(2) ?
C8 C9 H12 106.1 ?
C11 C9 H12 106.1 ?
C10 C9 H12 106.1 ?
C1 C10 C19 109.1(2) ?
C1 C10 C9 111.0(2) ?
C19 C10 C9 110.8(2) ?
C1 C10 C5 107.2(2) ?
C19 C10 C5 111.2(2) ?
C9 C10 C5 107.4(2) ?
C12 C11 C9 113.9(2) ?
C12 C11 H13 108.8 ?
C9 C11 H13 108.8 ?
C12 C11 H14 108.8 ?
C9 C11 H14 108.8 ?
H13 C11 H14 107.7 ?
C13 C12 C11 110.2(2) ?
C13 C12 H15 109.6 ?
C11 C12 H15 109.6 ?
C13 C12 H16 109.6 ?
C11 C12 H16 109.6 ?
H15 C12 H16 108.1 ?
C17 C13 C12 117.3(3) ?
C17 C13 C14 100.0(2) ?
C12 C13 C14 108.4(2) ?
C17 C13 C18 105.2(2) ?
C12 C13 C18 112.6(3) ?
C14 C13 C18 112.9(3) ?
C8 C14 C15 119.7(3) ?
C8 C14 C13 112.3(2) ?
C15 C14 C13 104.5(2) ?
C8 C14 H17 106.5 ?
C15 C14 H17 106.5 ?
C13 C14 H17 106.5 ?
C14 C15 C16 103.0(3) ?
C14 C15 H18 111.2 ?
C16 C15 H18 111.2 ?
C14 C15 H19 111.2 ?
C16 C15 H19 111.2 ?
H18 C15 H19 109.1 ?
C17 C16 C15 105.9(3) ?
C17 C16 H20 110.6 ?
C15 C16 H20 110.6 ?
C17 C16 H21 110.6 ?
C15 C16 H21 110.6 ?
H20 C16 H21 108.7 ?
O17 C17 C16 124.8(3) ?
O17 C17 C13 126.5(3) ?
C16 C17 C13 108.6(3) yes
C13 C18 H22 109.5 ?
C13 C18 H23 109.5 ?
H22 C18 H23 109.5 ?
C13 C18 H24 109.5 ?
H22 C18 H24 109.5 ?
H23 C18 H24 109.5 ?
C10 C19 H25 109.5 ?
C10 C19 H26 109.5 ?
H25 C19 H26 109.5 ?
C10 C19 H27 109.5 ?
H25 C19 H27 109.5 ?
H26 C19 H27 109.5 ?
C3 O3 H28 109.5 ?
C2' C1' C10' 113.8(3) ?
C2' C1' H1' 108.8 ?
C10' C1' H1' 108.8 ?
C2' C1' H2' 108.8 ?
C10' C1' H2' 108.8 ?
H1' C1' H2' 107.7 ?
C3' C2' C1' 111.4(3) ?
C3' C2' H3' 109.3 ?
C1' C2' H3' 109.3 ?
C3' C2' H4' 109.3 ?
C1' C2' H4' 109.3 ?
H3' C2' H4' 108.0 ?
O3' C3' C4' 111.2(3) ?
O3' C3' C2' 108.0(3) ?
C4' C3' C2' 108.7(3) yes
O3' C3' H5' 109.6 ?
C4' C3' H5' 109.6 ?
C2' C3' H5' 109.6 ?
O4' C4' C5' 123.4(3) ?
O4' C4' C3' 121.9(4) ?
C5' C4' C3' 114.5(3) yes
C4' C5' C6' 113.8(3) ?
C4' C5' C10' 108.1(3) ?
C6' C5' C10' 113.3(3) ?
C4' C5' H6' 107.1 ?
C6' C5' H6' 107.1 ?
C10' C5' H6' 107.1 ?
C7' C6' C5' 110.9(3) ?
C7' C6' H7' 109.5 ?
C5' C6' H7' 109.5 ?
C7' C6' H8' 109.5 ?
C5' C6' H8' 109.5 ?
H7' C6' H8' 108.1 ?
C6' C7' C8' 111.6(3) ?
C6' C7' H9' 109.3 ?
C8' C7' H9' 109.3 ?
C6' C7' H10' 109.3 ?
C8' C7' H10' 109.3 ?
H9' C7' H10' 108.0 ?
C7' C8' C14' 112.7(3) ?
C7' C8' C9' 111.2(2) ?
C14' C8' C9' 108.9(2) ?
C7' C8' H11' 107.9 ?
C14' C8' H11' 107.9 ?
C9' C8' H11' 107.9 ?
C11' C9' C10' 112.7(2) ?
C11' C9' C8' 113.0(2) ?
C10' C9' C8' 112.0(2) ?
C11' C9' H12' 106.2 ?
C10' C9' H12' 106.2 ?
C8' C9' H12' 106.2 ?
C19' C10' C1' 109.4(3) ?
C19' C10' C9' 111.5(3) ?
C1' C10' C9' 110.6(2) ?
C19' C10' C5' 110.8(3) ?
C1' C10' C5' 107.3(3) ?
C9' C10' C5' 107.1(2) ?
C12' C11' C9' 112.9(3) ?
C12' C11' H13' 109.0 ?
C9' C11' H13' 109.0 ?
C12' C11' H14' 109.0 ?
C9' C11' H14' 109.0 ?
H13' C11' H14' 107.8 ?
C13' C12' C11' 111.0(3) ?
C13' C12' H15' 109.4 ?
C11' C12' H15' 109.4 ?
C13' C12' H16' 109.4 ?
C11' C12' H16' 109.4 ?
H15' C12' H16' 108.0 ?
C17' C13' C12' 117.7(3) ?
C17' C13' C14' 101.1(3) ?
C12' C13' C14' 108.4(3) ?
C17' C13' C18' 104.7(3) ?
C12' C13' C18' 111.7(3) ?
C14' C13' C18' 113.0(3) ?
C13' C14' C8' 113.1(2) ?
C13' C14' C15' 104.0(3) ?
C8' C14' C15' 119.9(3) ?
C13' C14' H17' 106.3 ?
C8' C14' H17' 106.3 ?
C15' C14' H17' 106.3 ?
C14' C15' C16' 103.7(3) ?
C14' C15' H18' 111.0 ?
C16' C15' H18' 111.0 ?
C14' C15' H19' 111.0 ?
C16' C15' H19' 111.0 ?
H18' C15' H19' 109.0 ?
C17' C16' C15' 105.6(3) ?
C17' C16' H20' 110.6 ?
C15' C16' H20' 110.6 ?
C17' C16' H21' 110.6 ?
C15' C16' H21' 110.6 ?
H20' C16' H21' 108.7 ?
O17' C17' C16' 124.6(3) ?
O17' C17' C13' 126.9(3) ?
C16' C17' C13' 108.5(3) yes
C13' C18' H22' 109.5 ?
C13' C18' H23' 109.5 ?
H22' C18' H23' 109.5 ?
C13' C18' H24' 109.5 ?
H22' C18' H24' 109.5 ?
H23' C18' H24' 109.5 ?
C10' C19' H25' 109.5 ?
C10' C19' H26' 109.5 ?
H25' C19' H26' 109.5 ?
C10' C19' H27' 109.5 ?
H25' C19' H27' 109.5 ?
H26' C19' H27' 109.5 ?
C3' O3' H28' 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 C2 . 1.538(4) ?
C1 C10 . 1.537(4) ?
C1 H1 . 0.9700 ?
C1 H2 . 0.9700 ?
C2 C3 . 1.507(5) ?
C2 H3 . 0.9700 ?
C2 H4 . 0.9700 ?
C3 O3 . 1.429(4) yes
C3 C4 . 1.516(5) ?
C3 H5 . 0.9800 ?
C4 O4 . 1.213(4) yes
C4 C5 . 1.502(5) ?
C5 C6 . 1.517(4) ?
C5 C10 . 1.561(4) ?
C5 H6 . 0.9800 ?
C6 C7 . 1.515(5) ?
C6 H7 . 0.9700 ?
C6 H8 . 0.9700 ?
C7 C8 . 1.528(4) ?
C7 H9 . 0.9700 ?
C7 H10 . 0.9700 ?
C8 C14 . 1.515(4) ?
C8 C9 . 1.537(4) ?
C8 H11 . 0.9800 ?
C9 C11 . 1.542(4) ?
C9 C10 . 1.555(4) ?
C9 H12 . 0.9800 ?
C10 C19 . 1.545(4) ?
C11 C12 . 1.536(5) ?
C11 H13 . 0.9700 ?
C11 H14 . 0.9700 ?
C12 C13 . 1.518(4) ?
C12 H15 . 0.9700 ?
C12 H16 . 0.9700 ?
C13 C17 . 1.514(5) ?
C13 C14 . 1.539(4) ?
C13 C18 . 1.541(4) ?
C14 C15 . 1.529(4) ?
C14 H17 . 0.9800 ?
C15 C16 . 1.540(5) yes
C15 H18 . 0.9700 ?
C15 H19 . 0.9700 ?
C16 C17 . 1.509(5) yes
C16 H20 . 0.9700 ?
C16 H21 . 0.9700 ?
C17 O17 . 1.214(4) yes
C18 H22 . 0.9600 ?
C18 H23 . 0.9600 ?
C18 H24 . 0.9600 ?
C19 H25 . 0.9600 ?
C19 H26 . 0.9600 ?
C19 H27 . 0.9600 ?
O3 H28 . 0.8200 ?
C1' C2' . 1.528(5) ?
C1' C10' . 1.544(5) ?
C1' H1' . 0.9700 ?
C1' H2' . 0.9700 ?
C2' C3' . 1.515(6) ?
C2' H3' . 0.9700 ?
C2' H4' . 0.9700 ?
C3' O3' . 1.415(5) yes
C3' C4' . 1.515(5) ?
C3' H5' . 0.9800 ?
C4' O4' . 1.209(4) yes
C4' C5' . 1.503(5) ?
C5' C6' . 1.520(5) ?
C5' C10' . 1.557(4) ?
C5' H6' . 0.9800 ?
C6' C7' . 1.514(5) ?
C6' H7' . 0.9700 ?
C6' H8' . 0.9700 ?
C7' C8' . 1.517(4) ?
C7' H9' . 0.9700 ?
C7' H10' . 0.9700 ?
C8' C14' . 1.521(5) ?
C8' C9' . 1.547(4) ?
C8' H11' . 0.9800 ?
C9' C11' . 1.544(4) ?
C9' C10' . 1.546(4) ?
C9' H12' . 0.9800 ?
C10' C19' . 1.541(4) ?
C11' C12' . 1.536(5) ?
C11' H13' . 0.9700 ?
C11' H14' . 0.9700 ?
C12' C13' . 1.512(5) ?
C12' H15' . 0.9700 ?
C12' H16' . 0.9700 ?
C13' C17' . 1.507(5) ?
C13' C14' . 1.521(4) ?
C13' C18' . 1.544(4) ?
C14' C15' . 1.528(5) ?
C14' H17' . 0.9800 ?
C15' C16' . 1.532(6) yes
C15' H18' . 0.9700 ?
C15' H19' . 0.9700 ?
C16' C17' . 1.501(6) yes
C16' H20' . 0.9700 ?
C16' H21' . 0.9700 ?
C17' O17' . 1.218(4) yes
C18' H22' . 0.9600 ?
C18' H23' . 0.9600 ?
C18' H24' . 0.9600 ?
C19' H25' . 0.9600 ?
C19' H26' . 0.9600 ?
C19' H27' . 0.9600 ?
O3' H28' . 0.8200 ?
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 H28 O17 1_556 0.82 2.04 2.813(4) 158
O3' H28' O17' 1_556 0.82 1.98 2.790(4) 168
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
C10 C1 C2 C3 -55.6(3)
C1 C2 C3 O3 -68.4(3)
C1 C2 C3 C4 51.7(4)
O3 C3 C4 O4 -123.1(3)
C2 C3 C4 O4 118.3(3)
O3 C3 C4 C5 61.8(3)
C2 C3 C4 C5 -56.8(3)
O4 C4 C5 C6 13.0(4)
C3 C4 C5 C6 -171.9(2)
O4 C4 C5 C10 -113.8(3)
C3 C4 C5 C10 61.2(3)
C4 C5 C6 C7 179.2(2)
C10 C5 C6 C7 -56.7(3)
C5 C6 C7 C8 55.4(3)
C6 C7 C8 C14 -179.4(3)
C6 C7 C8 C9 -56.1(3)
C14 C8 C9 C11 -49.5(3)
C7 C8 C9 C11 -174.3(3)
C14 C8 C9 C10 -178.4(2)
C7 C8 C9 C10 56.9(3)
C2 C1 C10 C19 -63.4(3)
C2 C1 C10 C9 174.2(2)
C2 C1 C10 C5 57.2(3)
C8 C9 C10 C1 -172.0(2)
C11 C9 C10 C1 59.3(3)
C8 C9 C10 C19 66.6(3)
C11 C9 C10 C19 -62.1(3)
C8 C9 C10 C5 -55.1(3)
C11 C9 C10 C5 176.3(2)
C4 C5 C10 C1 -58.4(3)
C6 C5 C10 C1 175.1(2)
C4 C5 C10 C19 60.8(3)
C6 C5 C10 C19 -65.7(3)
C4 C5 C10 C9 -177.8(2)
C6 C5 C10 C9 55.7(3)
C8 C9 C11 C12 48.3(3)
C10 C9 C11 C12 176.5(3)
C9 C11 C12 C13 -52.7(4)
C11 C12 C13 C17 170.5(3)
C11 C12 C13 C14 58.3(3)
C11 C12 C13 C18 -67.2(3)
C7 C8 C14 C15 -54.9(3)
C9 C8 C14 C15 -178.9(3)
C7 C8 C14 C13 -178.0(2)
C9 C8 C14 C13 58.0(3)
C17 C13 C14 C8 173.4(2)
C12 C13 C14 C8 -63.2(3)
C18 C13 C14 C8 62.2(3)
C17 C13 C14 C15 42.2(3)
C12 C13 C14 C15 165.6(3)
C18 C13 C14 C15 -69.0(3)
C8 C14 C15 C16 -164.1(3)
C13 C14 C15 C16 -37.4(3)
C14 C15 C16 C17 17.3(4)
C15 C16 C17 O17 -168.9(3)
C15 C16 C17 C13 9.3(4)
C12 C13 C17 O17 29.8(4)
C14 C13 C17 O17 146.7(3)
C18 C13 C17 O17 -96.2(4)
C12 C13 C17 C16 -148.4(3)
C14 C13 C17 C16 -31.5(3)
C18 C13 C17 C16 85.7(3)
C10' C1' C2' C3' -55.0(5)
C1' C2' C3' O3' -68.7(4)
C1' C2' C3' C4' 52.1(5)
O3' C3' C4' O4' -124.6(4)
C2' C3' C4' O4' 116.6(4)
O3' C3' C4' C5' 60.3(4)
C2' C3' C4' C5' -58.5(4)
O4' C4' C5' C6' 13.8(5)
C3' C4' C5' C6' -171.2(3)
O4' C4' C5' C10' -113.0(4)
C3' C4' C5' C10' 62.1(4)
C4' C5' C6' C7' 178.9(3)
C10' C5' C6' C7' -57.1(4)
C5' C6' C7' C8' 54.9(4)
C6' C7' C8' C14' -177.8(3)
C6' C7' C8' C9' -55.1(4)
C7' C8' C9' C11' -174.5(3)
C14' C8' C9' C11' -49.7(3)
C7' C8' C9' C10' 56.8(3)
C14' C8' C9' C10' -178.3(2)
C2' C1' C10' C19' -63.7(4)
C2' C1' C10' C9' 173.1(3)
C2' C1' C10' C5' 56.6(4)
C11' C9' C10' C19' -63.0(3)
C8' C9' C10' C19' 65.7(3)
C11' C9' C10' C1' 59.0(3)
C8' C9' C10' C1' -172.3(3)
C11' C9' C10' C5' 175.6(3)
C8' C9' C10' C5' -55.6(3)
C4' C5' C10' C19' 61.8(3)
C6' C5' C10' C19' -65.3(4)
C4' C5' C10' C1' -57.6(3)
C6' C5' C10' C1' 175.3(3)
C4' C5' C10' C9' -176.4(2)
C6' C5' C10' C9' 56.5(3)
C10' C9' C11' C12' 177.1(3)
C8' C9' C11' C12' 48.8(4)
C9' C11' C12' C13' -53.1(4)
C11' C12' C13' C17' 172.2(3)
C11' C12' C13' C14' 58.4(4)
C11' C12' C13' C18' -66.7(4)
C17' C13' C14' C8' 172.8(3)
C12' C13' C14' C8' -62.9(3)
C18' C13' C14' C8' 61.5(3)
C17' C13' C14' C15' 41.1(3)
C12' C13' C14' C15' 165.5(3)
C18' C13' C14' C15' -70.2(3)
C7' C8' C14' C13' -178.2(3)
C9' C8' C14' C13' 57.8(3)
C7' C8' C14' C15' -55.0(4)
C9' C8' C14' C15' -179.0(3)
C13' C14' C15' C16' -36.4(4)
C8' C14' C15' C16' -164.0(3)
C14' C15' C16' C17' 16.9(4)
C15' C16' C17' O17' -171.7(4)
C15' C16' C17' C13' 8.9(4)
C12' C13' C17' O17' 31.9(5)
C14' C13' C17' O17' 149.6(4)
C18' C13' C17' O17' -92.8(4)
C12' C13' C17' C16' -148.7(3)
C14' C13' C17' C16' -31.0(3)
C18' C13' C17' C16' 86.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9855778
