#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/28/2212823.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_2212823
loop_
_publ_author_name
'Abdul Wahab Salae'
'Suchada Chantrapromma'
'Hoong-Kun Fun'
'Chanita Ponglimanont'
_publ_section_title
;
 ent-Kaur-16-ene-13,19-diol
;
_journal_coeditor_code           CI2312
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1899
_journal_page_last               o1901
_journal_paper_doi               10.1107/S1600536807012834
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H32 O2'
_chemical_formula_moiety         'C20 H32 O2'
_chemical_formula_sum            'C20 H32 O2'
_chemical_formula_weight         304.46
_chemical_melting_point          529.0(10)
_chemical_name_common
;
ent-Kaur-16-ene-13,19-diol
;
_chemical_name_systematic
;
ent-Kaur-16-ene-13,19-diol
;
_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                 97.907(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6496(4)
_cell_length_b                   7.8597(3)
_cell_length_c                   20.3159(7)
_cell_measurement_reflns_used    4787
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.00
_cell_measurement_theta_min      1.01
_cell_volume                     1684.33(11)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEX II CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19242
_diffrn_reflns_theta_full        29.55
_diffrn_reflns_theta_max         29.55
_diffrn_reflns_theta_min         1.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0428
_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)+(0.0583P)²+0.1985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                4395
_reflns_number_total             5031
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2312.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '528-530' was changed to '529.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '528-530' was changed to '529.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2212823
_cod_database_fobs_code          2212823
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
O O1A 0.64178(15) 0.1975(2) 0.27673(7) 0.0252(3) Uani d . 1
O O2A 0.56408(14) 0.2230(2) 0.71930(7) 0.0243(3) Uani d . 1
C C1A 0.71855(18) 0.0051(3) 0.49586(9) 0.0188(4) Uani d . 1
C C2A 0.7384(2) -0.1775(3) 0.47064(10) 0.0245(4) Uani d . 1
H H2AB 0.8256 -0.2111 0.4846 0.029 Uiso calc R 1
H H2AC 0.6843 -0.2550 0.4911 0.029 Uiso calc R 1
C C3A 0.7092(2) -0.1946(3) 0.39523(10) 0.0282(5) Uani d . 1
H H3AA 0.7267 -0.3102 0.3825 0.034 Uiso calc R 1
H H3AB 0.6198 -0.1724 0.3814 0.034 Uiso calc R 1
C C4A 0.7876(2) -0.0717(3) 0.35991(10) 0.0272(5) Uani d . 1
H H4AA 0.7618 -0.0820 0.3124 0.033 Uiso calc R 1
H H4AB 0.8759 -0.1053 0.3690 0.033 Uiso calc R 1
C C5A 0.77639(19) 0.1157(3) 0.37974(9) 0.0215(4) Uani d . 1
C C6A 0.79664(18) 0.1295(3) 0.45731(9) 0.0185(4) Uani d . 1
H H6AA 0.8847 0.0936 0.4702 0.022 Uiso calc R 1
C C7A 0.7930(2) 0.3104(3) 0.48440(9) 0.0214(4) Uani d . 1
H H7AA 0.7058 0.3479 0.4825 0.026 Uiso calc R 1
H H7AB 0.8361 0.3872 0.4576 0.026 Uiso calc R 1
C C8A 0.85853(19) 0.3139(3) 0.55675(9) 0.0228(4) Uani d . 1
H H8AA 0.9468 0.2825 0.5577 0.027 Uiso calc R 1
H H8AB 0.8559 0.4289 0.5738 0.027 Uiso calc R 1
C C9A 0.79720(18) 0.1939(3) 0.60212(9) 0.0182(4) Uani d . 1
C C10A 0.77826(18) 0.0143(3) 0.57104(9) 0.0189(4) Uani d . 1
H H10A 0.8644 -0.0299 0.5717 0.023 Uiso calc R 1
C C11A 0.7173(2) -0.1050(3) 0.61833(10) 0.0216(4) Uani d . 1
H H11A 0.6794 -0.2005 0.5926 0.026 Uiso calc R 1
H H11B 0.7841 -0.1498 0.6510 0.026 Uiso calc R 1
C C12A 0.6157(2) -0.0244(3) 0.65542(10) 0.0224(4) Uani d . 1
H H12A 0.5366 -0.0160 0.6255 0.027 Uiso calc R 1
H H12B 0.6014 -0.0973 0.6922 0.027 Uiso calc R 1
C C13A 0.65476(18) 0.1520(3) 0.68184(9) 0.0199(4) Uani d . 1
C C14A 0.67345(18) 0.2646(3) 0.62293(9) 0.0193(4) Uani d . 1
H H14A 0.6827 0.3832 0.6360 0.023 Uiso calc R 1
H H14B 0.6033 0.2535 0.5873 0.023 Uiso calc R 1
C C15A 0.87961(18) 0.1803(3) 0.67138(9) 0.0225(4) Uani d . 1
H H15A 0.9406 0.0885 0.6717 0.027 Uiso calc R 1
H H15B 0.9251 0.2857 0.6824 0.027 Uiso calc R 1
C C16A 0.78785(19) 0.1451(3) 0.72028(10) 0.0205(4) Uani d . 1
C C17A 0.57506(18) 0.0422(3) 0.48618(10) 0.0208(4) Uani d . 1
H H17A 0.5378 0.0025 0.4432 0.031 Uiso calc R 1
H H17B 0.5615 0.1625 0.4893 0.031 Uiso calc R 1
H H17C 0.5365 -0.0154 0.5200 0.031 Uiso calc R 1
C C18A 0.8833(2) 0.2151(4) 0.35268(10) 0.0286(5) Uani d . 1
H H18A 0.8828 0.1887 0.3065 0.043 Uiso calc R 1
H H18B 0.9636 0.1835 0.3771 0.043 Uiso calc R 1
H H18C 0.8700 0.3350 0.3576 0.043 Uiso calc R 1
C C19A 0.65014(19) 0.1916(3) 0.34806(9) 0.0243(5) Uani d . 1
H H19A 0.5810 0.1235 0.3603 0.029 Uiso calc R 1
H H19B 0.6416 0.3058 0.3650 0.029 Uiso calc R 1
C C20A 0.8130(2) 0.1195(3) 0.78496(10) 0.0235(4) Uani d . 1
H H20A 0.8964 0.1220 0.8058 0.028 Uiso calc R 1
H H20B 0.7474 0.0989 0.8097 0.028 Uiso calc R 1
O O1B 0.39586(16) 0.0197(3) 0.77040(8) 0.0302(4) Uani d . 1
O O2B 0.42173(16) 0.0349(2) 1.22463(8) 0.0264(3) Uani d . 1
C C1B 0.27791(18) 0.1997(3) 0.97099(9) 0.0176(4) Uani d . 1
C C2B 0.2448(2) 0.3767(3) 0.93981(11) 0.0235(4) Uani d . 1
H H2BB 0.1553 0.3982 0.9403 0.028 Uiso calc R 1
H H2BC 0.2918 0.4627 0.9672 0.028 Uiso calc R 1
C C3B 0.2741(2) 0.3949(3) 0.86863(11) 0.0277(5) Uani d . 1
H H3BA 0.2461 0.5059 0.8516 0.033 Uiso calc R 1
H H3BB 0.3650 0.3879 0.8686 0.033 Uiso calc R 1
C C4B 0.2091(2) 0.2576(3) 0.82328(10) 0.0264(5) Uani d . 1
H H4BA 0.2336 0.2710 0.7793 0.032 Uiso calc R 1
H H4BB 0.1181 0.2737 0.8194 0.032 Uiso calc R 1
C C5B 0.24126(19) 0.0758(3) 0.84777(10) 0.0205(4) Uani d . 1
C C6B 0.21579(18) 0.0623(3) 0.92142(9) 0.0178(4) Uani d . 1
H H6BA 0.1248 0.0851 0.9188 0.021 Uiso calc R 1
C C7B 0.23072(19) -0.1156(3) 0.95164(10) 0.0195(4) Uani d . 1
H H7BA 0.3198 -0.1397 0.9653 0.023 Uiso calc R 1
H H7BB 0.1976 -0.1995 0.9188 0.023 Uiso calc R 1
C C8B 0.15885(19) -0.1265(3) 1.01184(10) 0.0200(4) Uani d . 1
H H8BA 0.0692 -0.1093 0.9972 0.024 Uiso calc R 1
H H8BB 0.1694 -0.2397 1.0308 0.024 Uiso calc R 1
C C9B 0.20387(18) 0.0039(3) 1.06539(9) 0.0174(4) Uani d . 1
C C10B 0.21090(18) 0.1844(3) 1.03498(9) 0.0175(4) Uani d . 1
H H10B 0.1224 0.2149 1.0200 0.021 Uiso calc R 1
C C11B 0.2555(2) 0.3148(3) 1.09064(10) 0.0229(4) Uani d . 1
H H11C 0.2888 0.4138 1.0704 0.027 Uiso calc R 1
H H11D 0.1821 0.3514 1.1104 0.027 Uiso calc R 1
C C12B 0.3564(2) 0.2517(3) 1.14638(10) 0.0234(4) Uani d . 1
H H12C 0.4385 0.2529 1.1308 0.028 Uiso calc R 1
H H12D 0.3602 0.3288 1.1839 0.028 Uiso calc R 1
C C13B 0.3288(2) 0.0720(3) 1.16926(10) 0.0205(4) Uani d . 1
C C14B 0.32863(18) -0.0466(3) 1.10936(9) 0.0181(4) Uani d . 1
H H14C 0.3275 -0.1652 1.1225 0.022 Uiso calc R 1
H H14D 0.4016 -0.0264 1.0867 0.022 Uiso calc R 1
C C15B 0.11238(19) 0.0094(3) 1.11891(9) 0.0230(4) Uani d . 1
H H15C 0.0449 0.0909 1.1066 0.028 Uiso calc R 1
H H15D 0.0750 -0.1017 1.1237 0.028 Uiso calc R 1
C C16B 0.1920(2) 0.0620(3) 1.18283(10) 0.0228(4) Uani d . 1
C C17B 0.42266(18) 0.1852(3) 0.98662(10) 0.0219(4) Uani d . 1
H H17D 0.4609 0.2301 0.9502 0.033 Uiso calc R 1
H H17E 0.4460 0.0679 0.9933 0.033 Uiso calc R 1
H H17F 0.4517 0.2486 1.0262 0.033 Uiso calc R 1
C C18B 0.1541(2) -0.0497(3) 0.80514(10) 0.0262(5) Uani d . 1
H H18D 0.1470 -0.0164 0.7593 0.039 Uiso calc R 1
H H18E 0.0717 -0.0488 0.8192 0.039 Uiso calc R 1
H H18F 0.1893 -0.1621 0.8103 0.039 Uiso calc R 1
C C19B 0.3788(2) 0.0310(3) 0.83892(10) 0.0263(5) Uani d . 1
H H19C 0.4353 0.1173 0.8605 0.032 Uiso calc R 1
H H19D 0.4014 -0.0769 0.8605 0.032 Uiso calc R 1
C C20B 0.1534(3) 0.0917(3) 1.24102(11) 0.0318(5) Uani d . 1
H H20C 0.0680 0.0806 1.2456 0.038 Uiso calc R 1
H H20D 0.2116 0.1237 1.2773 0.038 Uiso calc R 1
H H1AA 0.581(3) 0.139(5) 0.2623(17) 0.057(11) Uiso d . 1
H H2AA 0.510(3) 0.154(5) 0.7321(17) 0.062(11) Uiso d . 1
H H1BA 0.376(3) -0.083(5) 0.7555(15) 0.044(9) Uiso d . 1
H H2BA 0.408(3) -0.059(5) 1.2357(14) 0.037(8) 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 0.0033 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
_geom_angle_publ_flag
C19A O1A H1AA 106(2) ?
C13A O2A H2AA 116(2) ?
C17A C1A C2A 108.10(17) ?
C17A C1A C6A 113.87(17) ?
C2A C1A C6A 107.94(15) ?
C17A C1A C10A 112.12(15) ?
C2A C1A C10A 107.96(17) ?
C6A C1A C10A 106.63(15) ?
C3A C2A C1A 113.28(19) ?
C3A C2A H2AB 108.9 ?
C1A C2A H2AB 108.9 ?
C3A C2A H2AC 108.9 ?
C1A C2A H2AC 108.9 ?
H2AB C2A H2AC 107.7 ?
C4A C3A C2A 111.65(19) ?
C4A C3A H3AA 109.3 ?
C2A C3A H3AA 109.3 ?
C4A C3A H3AB 109.3 ?
C2A C3A H3AB 109.3 ?
H3AA C3A H3AB 108.0 ?
C3A C4A C5A 114.71(17) ?
C3A C4A H4AA 108.6 ?
C5A C4A H4AA 108.6 ?
C3A C4A H4AB 108.6 ?
C5A C4A H4AB 108.6 ?
H4AA C4A H4AB 107.6 ?
C19A C5A C4A 111.05(19) ?
C19A C5A C18A 107.55(18) ?
C4A C5A C18A 107.74(18) ?
C19A C5A C6A 112.83(16) ?
C4A C5A C6A 109.01(18) ?
C18A C5A C6A 108.51(17) ?
C7A C6A C1A 111.13(15) ?
C7A C6A C5A 114.88(17) ?
C1A C6A C5A 116.91(17) ?
C7A C6A H6AA 104.0 ?
C1A C6A H6AA 104.0 ?
C5A C6A H6AA 104.0 ?
C6A C7A C8A 109.27(18) ?
C6A C7A H7AA 109.8 ?
C8A C7A H7AA 109.8 ?
C6A C7A H7AB 109.8 ?
C8A C7A H7AB 109.8 ?
H7AA C7A H7AB 108.3 ?
C9A C8A C7A 113.00(17) ?
C9A C8A H8AA 109.0 ?
C7A C8A H8AA 109.0 ?
C9A C8A H8AB 109.0 ?
C7A C8A H8AB 109.0 ?
H8AA C8A H8AB 107.8 ?
C8A C9A C14A 113.29(18) ?
C8A C9A C10A 111.07(15) ?
C14A C9A C10A 111.86(16) ?
C8A C9A C15A 110.69(16) ?
C14A C9A C15A 100.00(15) ?
C10A C9A C15A 109.38(17) ?
C11A C10A C9A 109.97(15) ?
C11A C10A C1A 115.27(17) ?
C9A C10A C1A 116.76(17) ?
C11A C10A H10A 104.4 ?
C9A C10A H10A 104.4 ?
C1A C10A H10A 104.4 ?
C12A C11A C10A 115.99(18) ?
C12A C11A H11A 108.3 ?
C10A C11A H11A 108.3 ?
C12A C11A H11B 108.3 ?
C10A C11A H11B 108.3 ?
H11A C11A H11B 107.4 ?
C13A C12A C11A 111.75(17) ?
C13A C12A H12A 109.3 ?
C11A C12A H12A 109.3 ?
C13A C12A H12B 109.3 ?
C11A C12A H12B 109.3 ?
H12A C12A H12B 107.9 ?
O2A C13A C16A 113.08(16) yes
O2A C13A C14A 111.33(18) yes
C16A C13A C14A 102.17(16) ?
O2A C13A C12A 111.87(17) yes
C16A C13A C12A 109.76(18) ?
C14A C13A C12A 108.12(16) ?
C13A C14A C9A 102.40(16) ?
C13A C14A H14A 111.3 ?
C9A C14A H14A 111.3 ?
C13A C14A H14B 111.3 ?
C9A C14A H14B 111.3 ?
H14A C14A H14B 109.2 ?
C16A C15A C9A 105.76(16) ?
C16A C15A H15A 110.6 ?
C9A C15A H15A 110.6 ?
C16A C15A H15B 110.6 ?
C9A C15A H15B 110.6 ?
H15A C15A H15B 108.7 ?
C20A C16A C15A 128.39(19) y
C20A C16A C13A 124.30(18) y
C15A C16A C13A 107.26(16) y
C1A C17A H17A 109.5 ?
C1A C17A H17B 109.5 ?
H17A C17A H17B 109.5 ?
C1A C17A H17C 109.5 ?
H17A C17A H17C 109.5 ?
H17B C17A H17C 109.5 ?
C5A C18A H18A 109.5 ?
C5A C18A H18B 109.5 ?
H18A C18A H18B 109.5 ?
C5A C18A H18C 109.5 ?
H18A C18A H18C 109.5 ?
H18B C18A H18C 109.5 ?
O1A C19A C5A 111.40(16) ?
O1A C19A H19A 109.3 ?
C5A C19A H19A 109.3 ?
O1A C19A H19B 109.3 ?
C5A C19A H19B 109.3 ?
H19A C19A H19B 108.0 ?
C16A C20A H20A 120.0 ?
C16A C20A H20B 120.0 ?
H20A C20A H20B 120.0 ?
C19B O1B H1BA 110(2) ?
C13B O2B H2BA 107(2) ?
C17B C1B C2B 108.47(17) ?
C17B C1B C6B 114.00(17) ?
C2B C1B C6B 107.78(16) ?
C17B C1B C10B 112.37(16) ?
C2B C1B C10B 107.68(16) ?
C6B C1B C10B 106.28(15) ?
C3B C2B C1B 114.02(18) ?
C3B C2B H2BB 108.7 ?
C1B C2B H2BB 108.7 ?
C3B C2B H2BC 108.7 ?
C1B C2B H2BC 108.7 ?
H2BB C2B H2BC 107.6 ?
C4B C3B C2B 111.82(19) ?
C4B C3B H3BA 109.3 ?
C2B C3B H3BA 109.3 ?
C4B C3B H3BB 109.3 ?
C2B C3B H3BB 109.3 ?
H3BA C3B H3BB 107.9 ?
C3B C4B C5B 113.62(17) ?
C3B C4B H4BA 108.8 ?
C5B C4B H4BA 108.8 ?
C3B C4B H4BB 108.8 ?
C5B C4B H4BB 108.8 ?
H4BA C4B H4BB 107.7 ?
C4B C5B C18B 108.90(17) ?
C4B C5B C19B 110.36(19) ?
C18B C5B C19B 107.29(18) ?
C4B C5B C6B 108.28(17) ?
C18B C5B C6B 108.99(17) ?
C19B C5B C6B 112.94(16) ?
C7B C6B C5B 115.21(17) ?
C7B C6B C1B 111.29(16) ?
C5B C6B C1B 117.21(17) ?
C7B C6B H6BA 103.7 ?
C5B C6B H6BA 103.7 ?
C1B C6B H6BA 103.7 ?
C6B C7B C8B 109.67(16) ?
C6B C7B H7BA 109.7 ?
C8B C7B H7BA 109.7 ?
C6B C7B H7BB 109.7 ?
C8B C7B H7BB 109.7 ?
H7BA C7B H7BB 108.2 ?
C9B C8B C7B 112.94(16) ?
C9B C8B H8BA 109.0 ?
C7B C8B H8BA 109.0 ?
C9B C8B H8BB 109.0 ?
C7B C8B H8BB 109.0 ?
H8BA C8B H8BB 107.8 ?
C8B C9B C14B 113.59(17) ?
C8B C9B C10B 110.99(15) ?
C14B C9B C10B 112.32(16) ?
C8B C9B C15B 110.58(16) ?
C14B C9B C15B 100.02(15) ?
C10B C9B C15B 108.76(16) ?
C11B C10B C9B 109.87(16) ?
C11B C10B C1B 115.08(17) ?
C9B C10B C1B 116.84(16) ?
C11B C10B H10B 104.5 ?
C9B C10B H10B 104.5 ?
C1B C10B H10B 104.5 ?
C12B C11B C10B 116.00(19) ?
C12B C11B H11C 108.3 ?
C10B C11B H11C 108.3 ?
C12B C11B H11D 108.3 ?
C10B C11B H11D 108.3 ?
H11C C11B H11D 107.4 ?
C13B C12B C11B 112.33(18) ?
C13B C12B H12C 109.1 ?
C11B C12B H12C 109.1 ?
C13B C12B H12D 109.1 ?
C11B C12B H12D 109.1 ?
H12C C12B H12D 107.9 ?
O2B C13B C16B 115.17(17) yes
O2B C13B C12B 106.76(17) yes
C16B C13B C12B 109.34(18) ?
O2B C13B C14B 115.36(18) yes
C16B C13B C14B 102.45(16) ?
C12B C13B C14B 107.46(16) ?
C13B C14B C9B 102.09(16) ?
C13B C14B H14C 111.4 ?
C9B C14B H14C 111.4 ?
C13B C14B H14D 111.4 ?
C9B C14B H14D 111.4 ?
H14C C14B H14D 109.2 ?
C16B C15B C9B 106.11(16) ?
C16B C15B H15C 110.5 ?
C9B C15B H15C 110.5 ?
C16B C15B H15D 110.5 ?
C9B C15B H15D 110.5 ?
H15C C15B H15D 108.7 ?
C20B C16B C15B 127.6(2) y
C20B C16B C13B 125.1(2) y
C15B C16B C13B 107.28(16) y
C1B C17B H17D 109.5 ?
C1B C17B H17E 109.5 ?
H17D C17B H17E 109.5 ?
C1B C17B H17F 109.5 ?
H17D C17B H17F 109.5 ?
H17E C17B H17F 109.5 ?
C5B C18B H18D 109.5 ?
C5B C18B H18E 109.5 ?
H18D C18B H18E 109.5 ?
C5B C18B H18F 109.5 ?
H18D C18B H18F 109.5 ?
H18E C18B H18F 109.5 ?
O1B C19B C5B 112.21(17) ?
O1B C19B H19C 109.2 ?
C5B C19B H19C 109.2 ?
O1B C19B H19D 109.2 ?
C5B C19B H19D 109.2 ?
H19C C19B H19D 107.9 ?
C16B C20B H20C 120.0 ?
C16B C20B H20D 120.0 ?
H20C C20B H20D 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C19A 1.440(2) y
O1A H1AA 0.81(4) ?
O2A C13A 1.423(2) y
O2A H2AA 0.85(4) ?
C1A C17A 1.541(3) ?
C1A C2A 1.548(3) ?
C1A C6A 1.562(3) ?
C1A C10A 1.573(3) ?
C2A C3A 1.527(3) ?
C2A H2AB 0.97 ?
C2A H2AC 0.97 ?
C3A C4A 1.519(3) ?
C3A H3AA 0.97 ?
C3A H3AB 0.97 ?
C4A C5A 1.536(4) ?
C4A H4AA 0.97 ?
C4A H4AB 0.97 ?
C5A C19A 1.530(3) ?
C5A C18A 1.543(3) ?
C5A C6A 1.565(3) ?
C6A C7A 1.527(3) ?
C6A H6AA 0.98 ?
C7A C8A 1.538(3) ?
C7A H7AA 0.97 ?
C7A H7AB 0.97 ?
C8A C9A 1.527(3) ?
C8A H8AA 0.97 ?
C8A H8AB 0.97 ?
C9A C14A 1.542(3) ?
C9A C10A 1.548(3) ?
C9A C15A 1.556(3) ?
C10A C11A 1.548(3) ?
C10A H10A 0.98 ?
C11A C12A 1.538(3) ?
C11A H11A 0.97 ?
C11A H11B 0.97 ?
C12A C13A 1.524(3) ?
C12A H12A 0.97 ?
C12A H12B 0.97 ?
C13A C16A 1.522(3) ?
C13A C14A 1.523(3) ?
C14A H14A 0.97 ?
C14A H14B 0.97 ?
C15A C16A 1.512(3) ?
C15A H15A 0.97 ?
C15A H15B 0.97 ?
C16A C20A 1.320(3) y
C17A H17A 0.96 ?
C17A H17B 0.96 ?
C17A H17C 0.96 ?
C18A H18A 0.96 ?
C18A H18B 0.96 ?
C18A H18C 0.96 ?
C19A H19A 0.97 ?
C19A H19B 0.97 ?
C20A H20A 0.93 ?
C20A H20B 0.93 ?
O1B C19B 1.431(2) y
O1B H1BA 0.88(4) ?
O2B C13B 1.422(3) y
O2B H2BA 0.79(3) ?
C1B C17B 1.535(3) ?
C1B C2B 1.548(3) ?
C1B C6B 1.561(3) ?
C1B C10B 1.571(3) ?
C2B C3B 1.527(3) ?
C2B H2BB 0.97 ?
C2B H2BC 0.97 ?
C3B C4B 1.522(4) ?
C3B H3BA 0.97 ?
C3B H3BB 0.97 ?
C4B C5B 1.536(3) ?
C4B H4BA 0.97 ?
C4B H4BB 0.97 ?
C5B C18B 1.537(3) ?
C5B C19B 1.541(3) ?
C5B C6B 1.561(3) ?
C6B C7B 1.526(3) ?
C6B H6BA 0.98 ?
C7B C8B 1.532(3) ?
C7B H7BA 0.97 ?
C7B H7BB 0.97 ?
C8B C9B 1.523(3) ?
C8B H8BA 0.97 ?
C8B H8BB 0.97 ?
C9B C14B 1.547(3) ?
C9B C10B 1.553(3) ?
C9B C15B 1.557(3) ?
C10B C11B 1.551(3) ?
C10B H10B 0.98 ?
C11B C12B 1.532(3) ?
C11B H11C 0.97 ?
C11B H11D 0.97 ?
C12B C13B 1.528(3) ?
C12B H12C 0.97 ?
C12B H12D 0.97 ?
C13B C16B 1.522(3) ?
C13B C14B 1.533(3) ?
C14B H14C 0.97 ?
C14B H14D 0.97 ?
C15B C16B 1.508(3) ?
C15B H15C 0.97 ?
C15B H15D 0.97 ?
C16B C20B 1.325(3) y
C17B H17D 0.96 ?
C17B H17E 0.96 ?
C17B H17F 0.96 ?
C18B H18D 0.96 ?
C18B H18E 0.96 ?
C18B H18F 0.96 ?
C19B H19C 0.97 ?
C19B H19D 0.97 ?
C20B H20C 0.93 ?
C20B H20D 0.93 ?
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
_geom_hbond_publ_flag
O1A H1AA O2B 1_554 0.81(3) 1.94(3) 2.750(2) 171(4) y
O2A H2AA O1B 1_555 0.86(4) 1.86(4) 2.711(2) 172(3) y
O1B H1BA O1A 2_646 0.88(4) 1.85(4) 2.718(3) 172(3) y
O2B H2BA O2A 2_647 0.79(4) 1.95(4) 2.699(2) 159(3) y
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
C17A C1A C2A C3A 70.2(2)
C6A C1A C2A C3A -53.4(2)
C10A C1A C2A C3A -168.31(17)
C1A C2A C3A C4A 56.6(3)
C2A C3A C4A C5A -54.6(3)
C3A C4A C5A C19A -75.5(2)
C3A C4A C5A C18A 166.94(18)
C3A C4A C5A C6A 49.4(2)
C17A C1A C6A C7A 65.8(2)
C2A C1A C6A C7A -174.15(17)
C10A C1A C6A C7A -58.4(2)
C17A C1A C6A C5A -68.8(2)
C2A C1A C6A C5A 51.3(2)
C10A C1A C6A C5A 167.06(17)
C19A C5A C6A C7A -58.3(2)
C4A C5A C6A C7A 177.81(17)
C18A C5A C6A C7A 60.7(2)
C19A C5A C6A C1A 74.6(2)
C4A C5A C6A C1A -49.3(2)
C18A C5A C6A C1A -166.34(18)
C1A C6A C7A C8A 64.1(2)
C5A C6A C7A C8A -160.33(16)
C6A C7A C8A C9A -58.6(2)
C7A C8A C9A C14A -77.8(2)
C7A C8A C9A C10A 49.1(2)
C7A C8A C9A C15A 170.79(18)
C8A C9A C10A C11A 179.42(16)
C14A C9A C10A C11A -52.9(2)
C15A C9A C10A C11A 56.9(2)
C8A C9A C10A C1A -46.8(2)
C14A C9A C10A C1A 80.9(2)
C15A C9A C10A C1A -169.28(15)
C17A C1A C10A C11A 56.7(2)
C2A C1A C10A C11A -62.3(2)
C6A C1A C10A C11A -178.05(17)
C17A C1A C10A C9A -74.7(2)
C2A C1A C10A C9A 166.34(16)
C6A C1A C10A C9A 50.6(2)
C9A C10A C11A C12A 38.2(2)
C1A C10A C11A C12A -96.3(2)
C10A C11A C12A C13A -42.8(2)
C11A C12A C13A O2A -176.78(17)
C11A C12A C13A C16A -50.4(2)
C11A C12A C13A C14A 60.3(2)
O2A C13A C14A C9A 164.88(16)
C16A C13A C14A C9A 43.90(19)
C12A C13A C14A C9A -71.85(19)
C8A C9A C14A C13A -163.74(16)
C10A C9A C14A C13A 69.79(19)
C15A C9A C14A C13A -45.92(19)
C8A C9A C15A C16A 150.37(19)
C14A C9A C15A C16A 30.6(2)
C10A C9A C15A C16A -86.92(19)
C9A C15A C16A C20A 178.2(2)
C9A C15A C16A C13A -4.4(2)
O2A C13A C16A C20A 33.5(3)
C14A C13A C16A C20A 153.3(2)
C12A C13A C16A C20A -92.2(3)
O2A C13A C16A C15A -144.01(19)
C14A C13A C16A C15A -24.2(2)
C12A C13A C16A C15A 90.3(2)
C4A C5A C19A O1A -65.0(2)
C18A C5A C19A O1A 52.7(2)
C6A C5A C19A O1A 172.30(19)
C17B C1B C2B C3B 72.8(2)
C6B C1B C2B C3B -51.1(2)
C10B C1B C2B C3B -165.33(18)
C1B C2B C3B C4B 55.4(2)
C2B C3B C4B C5B -55.8(2)
C3B C4B C5B C18B 170.59(18)
C3B C4B C5B C19B -71.9(2)
C3B C4B C5B C6B 52.2(2)
C4B C5B C6B C7B 174.33(17)
C18B C5B C6B C7B 56.0(2)
C19B C5B C6B C7B -63.1(2)
C4B C5B C6B C1B -51.8(2)
C18B C5B C6B C1B -170.11(17)
C19B C5B C6B C1B 70.8(2)
C17B C1B C6B C7B 66.1(2)
C2B C1B C6B C7B -173.44(16)
C10B C1B C6B C7B -58.2(2)
C17B C1B C6B C5B -69.5(2)
C2B C1B C6B C5B 51.0(2)
C10B C1B C6B C5B 166.16(16)
C5B C6B C7B C8B -159.46(16)
C1B C6B C7B C8B 64.0(2)
C6B C7B C8B C9B -58.3(2)
C7B C8B C9B C14B -78.8(2)
C7B C8B C9B C10B 48.9(2)
C7B C8B C9B C15B 169.71(17)
C8B C9B C10B C11B 179.39(16)
C14B C9B C10B C11B -52.2(2)
C15B C9B C10B C11B 57.5(2)
C8B C9B C10B C1B -47.1(2)
C14B C9B C10B C1B 81.2(2)
C15B C9B C10B C1B -169.00(16)
C17B C1B C10B C11B 56.6(2)
C2B C1B C10B C11B -62.8(2)
C6B C1B C10B C11B -178.11(16)
C17B C1B C10B C9B -74.5(2)
C2B C1B C10B C9B 166.07(16)
C6B C1B C10B C9B 50.8(2)
C9B C10B C11B C12B 37.4(2)
C1B C10B C11B C12B -97.0(2)
C10B C11B C12B C13B -43.0(2)
C11B C12B C13B O2B -174.73(17)
C11B C12B C13B C16B -49.5(2)
C11B C12B C13B C14B 61.0(2)
O2B C13B C14B C9B 169.23(17)
C16B C13B C14B C9B 43.30(19)
C12B C13B C14B C9B -71.85(19)
C8B C9B C14B C13B -163.31(16)
C10B C9B C14B C13B 69.69(19)
C15B C9B C14B C13B -45.50(19)
C8B C9B C15B C16B 150.98(18)
C14B C9B C15B C16B 31.0(2)
C10B C9B C15B C16B -86.9(2)
C9B C15B C16B C20B 176.3(2)
C9B C15B C16B C13B -4.9(2)
O2B C13B C16B C20B 29.1(3)
C12B C13B C16B C20B -91.0(3)
C14B C13B C16B C20B 155.2(2)
O2B C13B C16B C15B -149.72(19)
C12B C13B C16B C15B 90.1(2)
C14B C13B C16B C15B -23.7(2)
C4B C5B C19B O1B -67.2(2)
C18B C5B C19B O1B 51.3(3)
C6B C5B C19B O1B 171.42(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24737395
