#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:19:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178430 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025119.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_4025119
loop_
_publ_author_name
'Liang-Feng Yao'
'Yin Wei'
'Min Shi'
_publ_section_title
;
Silver- and Gold-Catalyzed Intramolecular Rearrangement of Propargylic
Alcohols Tethered with Methylenecyclopropanes: Stereoselective Synthesis of
Allenylcyclobutanols and 1-Vinyl-3-oxabicyclo[3.2.1]octan-8-one Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9466
_journal_page_last               9469
_journal_paper_doi               10.1021/jo902261r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C28 H26 O3'
_chemical_formula_weight         410.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.179(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5410(18)
_cell_length_b                   16.611(2)
_cell_length_c                   10.4723(14)
_cell_measurement_reflns_used    962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.908
_cell_measurement_theta_min      4.772
_cell_volume                     2237.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1409
_diffrn_reflns_av_sigmaI/netI    0.1694
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11956
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75149
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc 
 [0.00000+1.00000exp(3.00(sinθ/λ)²)]/ 
   [σ²(Fo²)+0.0000+0.0000*P+(0.0000P)²+0.0000sinθ/λ] 
 where P = 0.33333Fo² + 0.66667Fc² 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                1745
_reflns_number_total             4382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902261r_si_002.cif
_cod_data_source_block           cd29237
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4025119
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11518(12) 0.32516(12) 0.37296(16) 0.0558(5) Uani 1 1 d . . .
H1 H 0.0588 0.3048 0.3329 0.084 Uiso 1 1 calc R . .
O2 O 0.35311(15) 0.30366(12) 0.23435(19) 0.0679(6) Uani 1 1 d . . .
O3 O 0.08961(15) 0.75575(13) 0.2697(2) 0.0779(6) Uani 1 1 d . . .
C1 C 0.15983(18) 0.35851(15) 0.2782(2) 0.0418(6) Uani 1 1 d . . .
C2 C 0.09476(19) 0.41978(17) 0.1736(2) 0.0492(7) Uani 1 1 d . . .
H2 H 0.0222 0.4022 0.1487 0.059 Uiso 1 1 calc R . .
C3 C 0.1423(2) 0.38136(17) 0.0725(2) 0.0594(8) Uani 1 1 d . . .
H3A H 0.0928 0.3733 -0.0162 0.071 Uiso 1 1 calc R . .
H3B H 0.2043 0.4085 0.0670 0.071 Uiso 1 1 calc R . .
C4 C 0.1646(2) 0.30545(17) 0.1588(2) 0.0539(7) Uani 1 1 d . . .
H4 H 0.1040 0.2698 0.1317 0.065 Uiso 1 1 calc R . .
C5 C 0.2616(2) 0.2574(2) 0.1740(3) 0.0736(9) Uani 1 1 d . . .
H5A H 0.2618 0.2104 0.2290 0.088 Uiso 1 1 calc R . .
H5B H 0.2620 0.2389 0.0863 0.088 Uiso 1 1 calc R . .
C6 C 0.35493(19) 0.32762(16) 0.3644(2) 0.0520(7) Uani 1 1 d . . .
H6A H 0.4212 0.3527 0.4101 0.062 Uiso 1 1 calc R . .
H6B H 0.3478 0.2806 0.4157 0.062 Uiso 1 1 calc R . .
C7 C 0.26783(17) 0.38638(15) 0.3579(2) 0.0395(6) Uani 1 1 d . . .
C8 C 0.28918(17) 0.45401(16) 0.4230(2) 0.0406(6) Uani 1 1 d . . .
C9 C 0.32182(16) 0.51900(15) 0.4974(2) 0.0391(6) Uani 1 1 d . . .
C10 C 0.36162(17) 0.58951(16) 0.4406(2) 0.0418(6) Uani 1 1 d . . .
C11 C 0.41331(19) 0.57868(18) 0.3471(2) 0.0544(7) Uani 1 1 d . . .
H11 H 0.4223 0.5270 0.3185 0.065 Uiso 1 1 calc R . .
C12 C 0.4519(2) 0.6441(2) 0.2953(3) 0.0719(9) Uani 1 1 d . . .
H12 H 0.4873 0.6360 0.2331 0.086 Uiso 1 1 calc R . .
C13 C 0.4380(2) 0.7210(2) 0.3358(3) 0.0734(10) Uani 1 1 d . . .
H13 H 0.4632 0.7650 0.3003 0.088 Uiso 1 1 calc R . .
C14 C 0.3871(2) 0.73243(18) 0.4283(3) 0.0652(8) Uani 1 1 d . . .
H14 H 0.3780 0.7843 0.4563 0.078 Uiso 1 1 calc R . .
C15 C 0.34923(19) 0.66766(16) 0.4802(3) 0.0525(7) Uani 1 1 d . . .
H15 H 0.3147 0.6763 0.5430 0.063 Uiso 1 1 calc R . .
C16 C 0.32149(17) 0.51883(14) 0.6396(2) 0.0400(6) Uani 1 1 d . . .
C17 C 0.40053(19) 0.55651(15) 0.7405(2) 0.0479(7) Uani 1 1 d . . .
H17 H 0.4514 0.5857 0.7182 0.057 Uiso 1 1 calc R . .
C18 C 0.4037(2) 0.55071(17) 0.8736(2) 0.0567(8) Uani 1 1 d . . .
H18 H 0.4566 0.5762 0.9400 0.068 Uiso 1 1 calc R . .
C19 C 0.3297(3) 0.5078(2) 0.9081(3) 0.0703(9) Uani 1 1 d . . .
H19 H 0.3331 0.5028 0.9978 0.084 Uiso 1 1 calc R . .
C20 C 0.2500(2) 0.47212(19) 0.8088(3) 0.0719(9) Uani 1 1 d . . .
H20 H 0.1983 0.4443 0.8317 0.086 Uiso 1 1 calc R . .
C21 C 0.2458(2) 0.47717(17) 0.6761(3) 0.0552(8) Uani 1 1 d . . .
H21 H 0.1918 0.4524 0.6104 0.066 Uiso 1 1 calc R . .
C22 C 0.09553(18) 0.50844(17) 0.1971(2) 0.0472(7) Uani 1 1 d . . .
C23 C 0.1400(2) 0.56265(19) 0.1305(3) 0.0599(8) Uani 1 1 d . . .
H23 H 0.1708 0.5429 0.0689 0.072 Uiso 1 1 calc R . .
C24 C 0.1404(2) 0.64444(19) 0.1516(3) 0.0651(8) Uani 1 1 d . . .
H24 H 0.1712 0.6788 0.1050 0.078 Uiso 1 1 calc R . .
C25 C 0.0956(2) 0.67483(18) 0.2405(3) 0.0595(8) Uani 1 1 d . . .
C26 C 0.0495(2) 0.6227(2) 0.3094(3) 0.0638(8) Uani 1 1 d . . .
H26 H 0.0186 0.6431 0.3705 0.077 Uiso 1 1 calc R . .
C27 C 0.0497(2) 0.54090(18) 0.2869(3) 0.0575(8) Uani 1 1 d . . .
H27 H 0.0184 0.5067 0.3330 0.069 Uiso 1 1 calc R . .
C28 C 0.1453(2) 0.81068(19) 0.2125(4) 0.0977(12) Uani 1 1 d . . .
H28A H 0.2170 0.7950 0.2376 0.146 Uiso 1 1 calc R . .
H28B H 0.1401 0.8640 0.2450 0.146 Uiso 1 1 calc R . .
H28C H 0.1162 0.8099 0.1163 0.146 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C6 O2 C5 109.3(2) . . ?
C25 O3 C28 116.9(2) . . ?
O1 C1 C7 106.39(18) . . ?
O1 C1 C4 118.4(2) . . ?
C7 C1 C4 110.1(2) . . ?
O1 C1 C2 118.39(19) . . ?
C7 C1 C2 115.3(2) . . ?
C4 C1 C2 87.73(18) . . ?
C22 C2 C3 122.7(2) . . ?
C22 C2 C1 123.9(2) . . ?
C3 C2 C1 86.95(19) . . ?
C22 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C1 C2 H2 107.1 . . ?
C4 C3 C2 89.02(19) . . ?
C4 C3 H3A 113.8 . . ?
C2 C3 H3A 113.8 . . ?
C4 C3 H3B 113.8 . . ?
C2 C3 H3B 113.8 . . ?
H3A C3 H3B 111.0 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 C1 118.2(2) . . ?
C3 C4 C1 87.6(2) . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
C1 C4 H4 109.6 . . ?
O2 C5 C4 111.8(2) . . ?
O2 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
O2 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
O2 C6 C7 111.1(2) . . ?
O2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
O2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C1 124.9(2) . . ?
C8 C7 C6 119.4(2) . . ?
C1 C7 C6 115.6(2) . . ?
C7 C8 C9 173.1(3) . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 C16 118.8(2) . . ?
C10 C9 C16 121.0(2) . . ?
C11 C10 C15 117.9(2) . . ?
C11 C10 C9 120.5(2) . . ?
C15 C10 C9 121.6(2) . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C21 C16 C17 118.3(2) . . ?
C21 C16 C9 120.6(2) . . ?
C17 C16 C9 121.0(2) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C16 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C23 C22 C27 116.4(3) . . ?
C23 C22 C2 122.6(2) . . ?
C27 C22 C2 120.9(2) . . ?
C24 C23 C22 122.7(3) . . ?
C24 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 O3 125.5(3) . . ?
C24 C25 C26 119.5(3) . . ?
O3 C25 C26 115.0(3) . . ?
C27 C26 C25 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C22 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
O3 C28 H28A 109.5 . . ?
O3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.425(3) . ?
O1 H1 0.8200 . ?
O2 C6 1.411(3) . ?
O2 C5 1.427(3) . ?
O3 C25 1.386(3) . ?
O3 C28 1.429(3) . ?
C1 C7 1.512(3) . ?
C1 C4 1.548(3) . ?
C1 C2 1.553(3) . ?
C2 C22 1.493(3) . ?
C2 C3 1.539(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.526(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.503(4) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.516(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.299(3) . ?
C8 C9 1.324(3) . ?
C9 C10 1.488(3) . ?
C9 C16 1.491(3) . ?
C10 C11 1.382(3) . ?
C10 C15 1.388(3) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.385(3) . ?
C16 C17 1.396(3) . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.386(4) . ?
C22 C27 1.386(3) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.393(4) . ?
C26 C27 1.380(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
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
O1 H1 O3 0.82 2.12 2.944(3) 178.1 2_545
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
O1 C1 C2 C22 88.9(3) . . . . ?
C7 C1 C2 C22 -38.7(3) . . . . ?
C4 C1 C2 C22 -149.8(2) . . . . ?
O1 C1 C2 C3 -143.1(2) . . . . ?
C7 C1 C2 C3 89.3(2) . . . . ?
C4 C1 C2 C3 -21.85(19) . . . . ?
C22 C2 C3 C4 151.1(2) . . . . ?
C1 C2 C3 C4 22.17(18) . . . . ?
C2 C3 C4 C5 -143.8(2) . . . . ?
C2 C3 C4 C1 -22.23(18) . . . . ?
O1 C1 C4 C5 -93.1(3) . . . . ?
C7 C1 C4 C5 29.4(3) . . . . ?
C2 C1 C4 C5 145.6(3) . . . . ?
O1 C1 C4 C3 143.3(2) . . . . ?
C7 C1 C4 C3 -94.1(2) . . . . ?
C2 C1 C4 C3 22.04(18) . . . . ?
C6 O2 C5 C4 61.5(3) . . . . ?
C3 C4 C5 O2 61.1(3) . . . . ?
C1 C4 C5 O2 -43.9(3) . . . . ?
C5 O2 C6 C7 -66.7(3) . . . . ?
O1 C1 C7 C8 -81.4(3) . . . . ?
C4 C1 C7 C8 149.2(2) . . . . ?
C2 C1 C7 C8 52.0(3) . . . . ?
O1 C1 C7 C6 96.0(2) . . . . ?
C4 C1 C7 C6 -33.4(3) . . . . ?
C2 C1 C7 C6 -130.7(2) . . . . ?
O2 C6 C7 C8 -128.6(2) . . . . ?
O2 C6 C7 C1 53.8(3) . . . . ?
C1 C7 C8 C9 161(2) . . . . ?
C6 C7 C8 C9 -16(2) . . . . ?
C7 C8 C9 C10 102(2) . . . . ?
C7 C8 C9 C16 -76(2) . . . . ?
C8 C9 C10 C11 -32.5(3) . . . . ?
C16 C9 C10 C11 145.2(2) . . . . ?
C8 C9 C10 C15 148.1(2) . . . . ?
C16 C9 C10 C15 -34.2(3) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
C9 C10 C11 C12 -179.0(2) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C11 C10 C15 C14 0.0(4) . . . . ?
C9 C10 C15 C14 179.4(2) . . . . ?
C8 C9 C16 C21 -33.3(3) . . . . ?
C10 C9 C16 C21 149.0(2) . . . . ?
C8 C9 C16 C17 142.9(2) . . . . ?
C10 C9 C16 C17 -34.8(3) . . . . ?
C21 C16 C17 C18 1.2(4) . . . . ?
C9 C16 C17 C18 -175.0(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 -1.8(5) . . . . ?
C18 C19 C20 C21 1.9(5) . . . . ?
C19 C20 C21 C16 -0.5(4) . . . . ?
C17 C16 C21 C20 -1.1(4) . . . . ?
C9 C16 C21 C20 175.2(3) . . . . ?
C3 C2 C22 C23 -0.6(4) . . . . ?
C1 C2 C22 C23 110.1(3) . . . . ?
C3 C2 C22 C27 178.5(2) . . . . ?
C1 C2 C22 C27 -70.8(3) . . . . ?
C27 C22 C23 C24 0.6(4) . . . . ?
C2 C22 C23 C24 179.7(2) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C23 C24 C25 O3 -179.2(2) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C28 O3 C25 C24 -7.3(4) . . . . ?
C28 O3 C25 C26 173.5(2) . . . . ?
C24 C25 C26 C27 0.0(4) . . . . ?
O3 C25 C26 C27 179.2(2) . . . . ?
C25 C26 C27 C22 0.4(4) . . . . ?
C23 C22 C27 C26 -0.6(4) . . . . ?
C2 C22 C27 C26 -179.8(2) . . . . ?
