#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008579.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_2008579
loop_
_publ_author_name
'Al\'ias, M.'
'Bu\~nuel, E.'
'Cativiela, C.'
'D\'iaz-de-Villegas, M. D.'
'G\'alvez, J. A.'
_publ_section_title
;
 (1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>S</i>,5<i>S</i>,6<i>S</i>)-<i>exo</i>-2-Cyano-<i>exo</i>-3-[(<i>S</i>)-1,2-dibenzyloxyethyl]-<i>exo</i>-5-iodobicyclo[2.2.1]heptane-<i>endo</i>-2,6-carbolactone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1009
_journal_page_last               1012
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C25 H24 I N O4'
_chemical_formula_weight         529.35
_chemical_name_systematic
;
(1R,2R,3S,4S,5S,6S)-exo-3-[(S)-1,2-dibenzyloxyethyl]-exo-2-cyano-endo-6-
hydroxy-exo-5-iodobicyclo[2.2.1]heptane-endo-2-carboxylic Acid Lactone.
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4250(10)
_cell_length_b                   7.8950(10)
_cell_length_c                   21.883(2)
_cell_measurement_reflns_used    49
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.92
_cell_measurement_theta_min      6.00
_cell_volume                     1104.9(2)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1993)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1989)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4 diffractometer'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5013
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.481
_exptl_absorpt_correction_T_max  0.8660
_exptl_absorpt_correction_T_min  0.5619
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.652
_refine_ls_abs_structure_details 'Flack (1983). Friedel pairs = 1983'
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4315
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.1130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3886
_reflns_number_total             4315
_reflns_threshold_expression     F>4\s(F)
_[local]_cod_data_source_file    jz1323.cif
_[local]_cod_data_source_block   miriam
_[local]_cod_cif_authors_sg_H-M  'P 21'
_cod_database_code               2008579
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_type_symbol
I 0.51522(5) 0.74931(6) 0.898127(13) 0.04410(11) Uani d . 1 I
O1 -0.2407(6) 0.3062(6) 0.96527(19) 0.0550(12) Uani d . 1 O
O2 0.0583(6) 0.4547(6) 0.97827(17) 0.0478(10) Uani d . 1 O
O3 0.0366(5) 0.2324(7) 0.75167(14) 0.0376(8) Uani d . 1 O
O4 -0.2869(6) 0.4259(5) 0.67742(17) 0.0453(9) Uani d . 1 O
N -0.0819(9) -0.0360(7) 0.8659(3) 0.0613(14) Uani d . 1 N
C1 0.2647(7) 0.2956(6) 0.9123(2) 0.0355(12) Uani d . 1 C
H1 0.3345 0.2011 0.9349 0.043 Uiso calc R 1 H
C2 0.0275(6) 0.2746(10) 0.8935(2) 0.0344(17) Uani d . 1 C
C3 -0.0176(7) 0.4088(6) 0.8397(2) 0.0306(10) Uani d . 1 C
H3 -0.1144 0.4939 0.8532 0.037 Uiso calc R 1 H
C4 0.1992(7) 0.4935(6) 0.8381(2) 0.0311(10) Uani d . 1 C
H4 0.2192 0.5551 0.8002 0.037 Uiso calc R 1 H
C5 0.2340(8) 0.5994(7) 0.8975(2) 0.0367(11) Uani d . 1 C
H5 0.1131 0.6727 0.9017 0.044 Uiso calc R 1 H
C6 0.2509(8) 0.4635(7) 0.9479(2) 0.0375(11) Uani d . 1 C
H6 0.3737 0.4809 0.9774 0.045 Uiso calc R 1 H
C7 0.3529(8) 0.3468(7) 0.8534(2) 0.0362(11) Uani d . 1 C
H7A 0.3402 0.2579 0.8227 0.043 Uiso calc R 1 H
H7B 0.4970 0.3846 0.8601 0.043 Uiso calc R 1 H
C8 -0.0367(9) 0.1001(8) 0.8775(3) 0.0426(13) Uani d . 1 C
C9 -0.0750(8) 0.3389(8) 0.9493(2) 0.0413(12) Uani d . 1 C
C10 -0.1139(7) 0.3350(6) 0.7784(2) 0.0329(10) Uani d . 1 C
H10 -0.2335 0.2640 0.7862 0.039 Uiso calc R 1 H
C11 -0.1915(9) 0.4798(7) 0.7355(3) 0.0435(13) Uani d . 1 C
H11A -0.2917 0.5467 0.7556 0.052 Uiso calc R 1 H
H11B -0.0741 0.5527 0.7290 0.052 Uiso calc R 1 H
C12 -0.4959(9) 0.3699(9) 0.6783(3) 0.0500(14) Uani d . 1 C
H12A -0.5782 0.4570 0.6960 0.060 Uiso calc R 1 H
H12B -0.4995 0.2690 0.7034 0.060 Uiso calc R 1 H
C13 -0.5872(10) 0.3314(8) 0.6135(3) 0.0469(13) Uani d . 1 C
C14 -0.7881(10) 0.3838(10) 0.5941(3) 0.0612(17) Uani d . 1 C
H14 -0.8637 0.4478 0.6199 0.073 Uiso calc R 1 H
C15 -0.8772(12) 0.3401(12) 0.5353(4) 0.075(2) Uani d . 1 C
H15 -1.0136 0.3729 0.5227 0.090 Uiso calc R 1 H
C16 -0.7667(11) 0.251(2) 0.4969(3) 0.077(2) Uani d . 1 C
H16 -0.8248 0.2277 0.4572 0.092 Uiso calc R 1 H
C17 -0.5691(13) 0.1939(10) 0.5160(3) 0.071(2) Uani d . 1 C
H17 -0.4973 0.1256 0.4905 0.085 Uiso calc R 1 H
C18 -0.4773(9) 0.2394(17) 0.5740(3) 0.0594(15) Uani d . 1 C
H18 -0.3403 0.2072 0.5861 0.071 Uiso calc R 1 H
C19 -0.0502(10) 0.0934(8) 0.7156(3) 0.0554(16) Uani d . 1 C
H19A -0.1382 0.1356 0.6804 0.066 Uiso calc R 1 H
H19B -0.1354 0.0238 0.7399 0.066 Uiso calc R 1 H
C20 0.1232(10) -0.0089(7) 0.6947(3) 0.0460(13) Uani d . 1 C
C21 0.2889(10) -0.0612(8) 0.7368(3) 0.0514(14) Uani d . 1 C
H21 0.2891 -0.0345 0.7782 0.062 Uiso calc R 1 H
C22 0.4516(11) -0.1524(9) 0.7165(3) 0.0594(17) Uani d . 1 C
H22 0.5611 -0.1871 0.7446 0.071 Uiso calc R 1 H
C23 0.4551(13) -0.1928(9) 0.6558(4) 0.074(2) Uani d . 1 C
H23 0.5670 -0.2525 0.6424 0.089 Uiso calc R 1 H
C24 0.2895(15) -0.1435(10) 0.6146(4) 0.076(2) Uani d . 1 C
H24 0.2877 -0.1728 0.5734 0.091 Uiso calc R 1 H
C25 0.1283(12) -0.0517(9) 0.6343(3) 0.0631(18) Uani d . 1 C
H25 0.0194 -0.0175 0.6060 0.076 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I 0.04201(17) 0.04591(17) 0.04383(17) -0.0133(2) 0.00125(11) -0.0052(2)
O1 0.038(2) 0.076(3) 0.052(2) -0.0071(18) 0.0122(17) 0.0139(19)
O2 0.045(2) 0.064(3) 0.036(2) -0.0085(19) 0.0101(17) -0.0045(18)
O3 0.0318(14) 0.037(2) 0.0431(16) -0.0006(19) -0.0014(12) -0.008(2)
O4 0.041(2) 0.057(2) 0.0346(19) 0.0002(18) -0.0116(16) 0.0049(17)
N 0.058(3) 0.050(3) 0.074(4) -0.013(3) -0.001(3) 0.004(3)
C1 0.025(2) 0.037(3) 0.043(3) -0.0014(17) -0.0024(19) 0.0045(19)
C2 0.027(2) 0.036(5) 0.040(2) -0.001(2) -0.0006(17) 0.007(2)
C3 0.025(2) 0.031(2) 0.035(3) 0.0007(19) 0.001(2) 0.002(2)
C4 0.028(2) 0.036(2) 0.029(2) -0.0022(19) 0.0034(18) 0.000(2)
C5 0.032(2) 0.040(3) 0.038(3) -0.002(2) 0.001(2) -0.005(2)
C6 0.029(2) 0.050(3) 0.033(3) -0.003(2) 0.0008(19) 0.003(2)
C7 0.027(2) 0.038(3) 0.042(3) 0.003(2) -0.001(2) -0.006(2)
C8 0.035(3) 0.044(4) 0.047(3) -0.005(2) -0.002(2) 0.008(3)
C9 0.038(3) 0.051(3) 0.036(3) -0.001(2) 0.006(2) 0.009(2)
C10 0.027(2) 0.037(2) 0.033(2) 0.001(2) -0.0039(19) 0.000(2)
C11 0.045(3) 0.041(3) 0.042(3) 0.005(2) -0.011(2) 0.003(2)
C12 0.038(3) 0.070(4) 0.040(3) -0.003(3) -0.005(2) 0.005(3)
C13 0.047(3) 0.054(3) 0.039(3) -0.009(3) -0.004(2) 0.006(3)
C14 0.048(4) 0.070(4) 0.062(4) -0.002(3) -0.012(3) 0.007(3)
C15 0.054(4) 0.100(6) 0.067(5) -0.011(4) -0.021(4) 0.009(4)
C16 0.088(5) 0.093(5) 0.045(3) -0.021(8) -0.018(3) 0.011(7)
C17 0.091(5) 0.075(6) 0.046(3) -0.008(4) 0.003(3) -0.005(3)
C18 0.056(3) 0.072(4) 0.049(3) 0.004(5) -0.004(2) -0.009(6)
C19 0.049(3) 0.052(4) 0.061(4) 0.003(3) -0.017(3) -0.020(3)
C20 0.051(3) 0.039(3) 0.046(3) 0.000(2) -0.006(3) -0.004(2)
C21 0.061(4) 0.048(3) 0.043(3) 0.009(3) -0.005(3) -0.004(3)
C22 0.054(4) 0.048(4) 0.075(5) 0.015(3) -0.002(3) 0.005(3)
C23 0.081(5) 0.058(4) 0.085(5) 0.024(3) 0.023(4) 0.005(3)
C24 0.110(6) 0.065(5) 0.052(4) 0.025(4) 0.010(4) -0.007(3)
C25 0.078(5) 0.057(4) 0.050(4) 0.013(3) -0.014(3) -0.010(3)
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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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
C9 O2 C6 110.0(4) yes
C10 O3 C19 114.6(4) ?
C12 O4 C11 114.1(4) ?
C7 C1 C6 104.2(4) yes
C7 C1 C2 104.0(4) yes
C6 C1 C2 97.1(4) yes
C7 C1 H1 116.3 ?
C6 C1 H1 116.3 ?
C2 C1 H1 116.3 ?
C8 C2 C9 111.6(5) yes
C8 C2 C1 114.2(5) yes
C9 C2 C1 103.9(4) yes
C8 C2 C3 115.0(4) yes
C9 C2 C3 108.0(5) yes
C1 C2 C3 103.3(4) yes
C10 C3 C4 115.6(4) ?
C10 C3 C2 115.0(4) ?
C4 C3 C2 101.8(4) yes
C10 C3 H3 108.0 ?
C4 C3 H3 108.0 ?
C2 C3 H3 108.0 ?
C7 C4 C5 100.7(4) yes
C7 C4 C3 103.3(4) yes
C5 C4 C3 105.9(4) yes
C7 C4 H4 115.1 ?
C5 C4 H4 115.1 ?
C3 C4 H4 115.1 ?
C6 C5 C4 102.8(4) yes
C6 C5 I 112.2(3) yes
C4 C5 I 110.9(3) yes
C6 C5 H5 110.3 ?
C4 C5 H5 110.3 ?
I C5 H5 110.3 ?
O2 C6 C5 110.8(4) yes
O2 C6 C1 106.3(4) yes
C5 C6 C1 103.9(4) yes
O2 C6 H6 111.8 ?
C5 C6 H6 111.8 ?
C1 C6 H6 111.8 ?
C1 C7 C4 95.8(4) yes
C1 C7 H7A 112.6 ?
C4 C7 H7A 112.6 ?
C1 C7 H7B 112.6 ?
C4 C7 H7B 112.6 ?
H7A C7 H7B 110.1 ?
N C8 C2 178.4(6) yes
O1 C9 O2 123.6(5) yes
O1 C9 C2 129.3(6) yes
O2 C9 C2 107.1(4) yes
O3 C10 C11 111.5(4) ?
O3 C10 C3 109.9(4) ?
C11 C10 C3 109.4(4) ?
O3 C10 H10 108.7 ?
C11 C10 H10 108.7 ?
C3 C10 H10 108.7 ?
O4 C11 C10 114.3(5) ?
O4 C11 H11A 108.7 ?
C10 C11 H11A 108.7 ?
O4 C11 H11B 108.7 ?
C10 C11 H11B 108.7 ?
H11A C11 H11B 107.6 ?
O4 C12 C13 109.4(5) ?
O4 C12 H12A 109.8 ?
C13 C12 H12A 109.8 ?
O4 C12 H12B 109.8 ?
C13 C12 H12B 109.8 ?
H12A C12 H12B 108.2 ?
C18 C13 C14 119.0(6) ?
C18 C13 C12 121.3(6) ?
C14 C13 C12 119.7(6) ?
C13 C14 C15 119.8(7) ?
C13 C14 H14 120.1 ?
C15 C14 H14 120.1 ?
C16 C15 C14 120.5(7) ?
C16 C15 H15 119.7 ?
C14 C15 H15 119.7 ?
C15 C16 C17 120.4(6) ?
C15 C16 H16 119.8 ?
C17 C16 H16 119.8 ?
C16 C17 C18 119.4(8) ?
C16 C17 H17 120.3 ?
C18 C17 H17 120.3 ?
C13 C18 C17 120.7(7) ?
C13 C18 H18 119.7 ?
C17 C18 H18 119.7 ?
O3 C19 C20 108.8(5) ?
O3 C19 H19A 109.9 ?
C20 C19 H19A 109.9 ?
O3 C19 H19B 109.9 ?
C20 C19 H19B 109.9 ?
H19A C19 H19B 108.3 ?
C25 C20 C21 118.3(6) ?
C25 C20 C19 121.4(6) ?
C21 C20 C19 120.3(5) ?
C22 C21 C20 119.7(6) ?
C22 C21 H21 120.2 ?
C20 C21 H21 120.2 ?
C23 C22 C21 121.2(6) ?
C23 C22 H22 119.4 ?
C21 C22 H22 119.4 ?
C22 C23 C24 118.9(7) ?
C22 C23 H23 120.5 ?
C24 C23 H23 120.5 ?
C25 C24 C23 120.2(7) ?
C25 C24 H24 119.9 ?
C23 C24 H24 119.9 ?
C20 C25 C24 121.7(7) ?
C20 C25 H25 119.1 ?
C24 C25 H25 119.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I C5 2.159(5) yes
O1 C9 1.180(6) yes
O2 C9 1.367(7) yes
O2 C6 1.461(6) yes
O3 C10 1.428(6) ?
O3 C19 1.434(7) ?
O4 C12 1.415(7) ?
O4 C11 1.423(6) ?
N C8 1.135(8) yes
C1 C7 1.512(7) yes
C1 C6 1.545(7) yes
C1 C2 1.549(6) yes
C1 H1 0.9800 ?
C2 C8 1.470(9) yes
C2 C9 1.530(8) yes
C2 C3 1.590(8) yes
C3 C10 1.537(7) ?
C3 C4 1.548(7) yes
C3 H3 0.9800 ?
C4 C7 1.539(7) yes
C4 C5 1.544(7) yes
C4 H4 0.9800 ?
C5 C6 1.536(8) yes
C5 H5 0.9800 ?
C6 H6 0.9800 ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C10 C11 1.531(7) ?
C10 H10 0.9800 ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.513(8) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C18 1.375(11) ?
C13 C14 1.383(9) ?
C14 C15 1.399(10) ?
C14 H14 0.9300 ?
C15 C16 1.350(14) ?
C15 H15 0.9300 ?
C16 C17 1.374(12) ?
C16 H16 0.9300 ?
C17 C18 1.394(9) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C19 C20 1.483(9) ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 C25 1.367(9) ?
C20 C21 1.402(8) ?
C21 C22 1.377(9) ?
C21 H21 0.9300 ?
C22 C23 1.370(11) ?
C22 H22 0.9300 ?
C23 C24 1.383(11) ?
C23 H23 0.9300 ?
C24 C25 1.367(11) ?
C24 H24 0.9300 ?
C25 H25 0.9300 ?
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
C7 C1 C2 C8 94.5(5)
C6 C1 C2 C8 -158.9(5)
C7 C1 C2 C9 -143.8(5)
C6 C1 C2 C9 -37.1(5)
C7 C1 C2 C3 -31.1(5)
C6 C1 C2 C3 75.5(5)
C8 C2 C3 C10 -2.2(6)
C9 C2 C3 C10 -127.5(5)
C1 C2 C3 C10 122.9(5)
C8 C2 C3 C4 -128.0(4)
C9 C2 C3 C4 106.8(4)
C1 C2 C3 C4 -2.9(5)
C10 C3 C4 C7 -90.1(5)
C2 C3 C4 C7 35.3(5)
C10 C3 C4 C5 164.5(4)
C2 C3 C4 C5 -70.2(5)
C7 C4 C5 C6 -41.0(5)
C3 C4 C5 C6 66.3(5)
C7 C4 C5 I 79.0(4)
C3 C4 C5 I -173.7(3)
C9 O2 C6 C5 91.0(5)
C9 O2 C6 C1 -21.3(5)
C4 C5 C6 O2 -103.8(5)
I C5 C6 O2 137.1(4)
C4 C5 C6 C1 10.0(5)
I C5 C6 C1 -109.1(4)
C7 C1 C6 O2 142.1(4)
C2 C1 C6 O2 35.7(5)
C7 C1 C6 C5 25.1(5)
C2 C1 C6 C5 -81.3(4)
C6 C1 C7 C4 -49.4(4)
C2 C1 C7 C4 51.8(5)
C5 C4 C7 C1 55.3(4)
C3 C4 C7 C1 -54.0(4)
C9 C2 C8 N -10E1(3)
C1 C2 C8 N 1E1(3)
C3 C2 C8 N 13E1(3)
C6 O2 C9 O1 179.0(5)
C6 O2 C9 C2 -4.1(6)
C8 C2 C9 O1 -32.3(8)
C1 C2 C9 O1 -155.8(6)
C3 C2 C9 O1 95.0(7)
C8 C2 C9 O2 151.1(4)
C1 C2 C9 O2 27.6(6)
C3 C2 C9 O2 -81.6(5)
C19 O3 C10 C11 -89.6(6)
C19 O3 C10 C3 148.9(5)
C4 C3 C10 O3 49.0(6)
C2 C3 C10 O3 -69.3(5)
C4 C3 C10 C11 -73.7(5)
C2 C3 C10 C11 168.0(4)
C12 O4 C11 C10 79.2(6)
O3 C10 C11 O4 59.1(6)
C3 C10 C11 O4 -179.1(4)
C11 O4 C12 C13 174.8(5)
O4 C12 C13 C18 45.8(10)
O4 C12 C13 C14 -136.7(6)
C18 C13 C14 C15 1.1(12)
C12 C13 C14 C15 -176.4(7)
C13 C14 C15 C16 -1.6(13)
C14 C15 C16 C17 3.4(17)
C15 C16 C17 C18 -4.6(17)
C14 C13 C18 C17 -2.3(14)
C12 C13 C18 C17 175.1(8)
C16 C17 C18 C13 4.1(15)
C10 O3 C19 C20 -175.8(5)
O3 C19 C20 C25 -129.1(7)
O3 C19 C20 C21 49.6(8)
C25 C20 C21 C22 0.4(10)
C19 C20 C21 C22 -178.3(6)
C20 C21 C22 C23 0.2(11)
C21 C22 C23 C24 -1.3(12)
C22 C23 C24 C25 1.8(13)
C21 C20 C25 C24 0.1(11)
C19 C20 C25 C24 178.9(7)
C23 C24 C25 C20 -1.3(13)