#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/01/2240124.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_2240124
loop_
_publ_author_name
'Penthala, Narsimha Reddy'
'Madadi, Nikhil Reddy'
'Bommagani, Shobanbabu'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;
 Comparison of crystal structures of
 4-(benzo[b]thiophen-2-yl)-5-(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole
 and
 4-(benzo[b]thiophen-2-yl)-2-methyl-5-(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole
;
_journal_coeditor_code           HG5414
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              392
_journal_page_last               395
_journal_paper_doi               10.1107/S1600536814023095
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H19 N3 O3 S'
_chemical_formula_moiety         'C20 H19 N3 O3 S'
_chemical_formula_sum            'C20 H19 N3 O3 S'
_chemical_formula_weight         381.44
_chemical_name_systematic
4-(Benzo[b]thiophen-2-yl)-2-methyl-5-(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                106.859(4)
_cell_angle_beta                 111.668(5)
_cell_angle_gamma                105.498(4)
_cell_formula_units_Z            2
_cell_length_a                   8.85790(10)
_cell_length_b                   11.07610(10)
_cell_length_c                   11.26260(10)
_cell_measurement_reflns_used    4076
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     891.51(7)
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 2006)
;
_computing_data_collection
;
COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO-SMN (Otwinowski & Minor, 2006)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008b)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2008b) and CIFFIX (Parkin,
2013)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008b)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008b)
;
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36591
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         2.118
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2008a)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     161
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0472P)²+0.4023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                3572
_reflns_number_total             4097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5414sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        891.51(4)
_cod_database_code               2240124
_cod_database_fobs_code          2240124
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.41837(14) 0.62237(11) 0.61716(11) 0.0160(2) Uani d 1 . .
N N2 0.56418(15) 0.73837(11) 0.71234(11) 0.0158(2) Uani d 1 . .
N N3 0.65185(15) 0.80574(11) 0.66113(11) 0.0163(2) Uani d 1 . .
O O1 0.75768(14) 1.08896(10) 0.37490(10) 0.0234(2) Uani d 1 . .
O O2 0.77188(12) 0.90655(10) 0.16639(9) 0.0178(2) Uani d 1 . .
O O3 0.72458(13) 0.64975(10) 0.14267(10) 0.0197(2) Uani d 1 . .
C C1 0.2506(5) 0.5036(4) 0.36036(19) 0.0145(4) Uani d 0.9363(14) A 1
S S1 0.08551(5) 0.39081(4) 0.37446(4) 0.01741(12) Uani d 0.9363(14) A 1
C C2 0.2034(2) 0.48053(18) 0.22483(17) 0.0176(3) Uani d 0.9363(14) A 1
H H2 0.2776 0.5336 0.1986 0.021 Uiso calc 0.9363(14) A 1
C C3 0.0313(3) 0.3687(3) 0.1242(2) 0.0164(4) Uani d 0.9363(14) A 1
C C4 -0.0638(3) 0.31782(16) -0.0245(2) 0.0203(4) Uani d 0.9363(14) A 1
H H4 -0.0117 0.3565 -0.0725 0.024 Uiso calc 0.9363(14) A 1
C C5 -0.2341(3) 0.21078(18) -0.09952(19) 0.0210(4) Uani d 0.9363(14) A 1
H H5 -0.2990 0.1766 -0.1996 0.025 Uiso calc 0.9363(14) A 1
C C6 -0.3125(2) 0.1519(2) -0.03024(16) 0.0195(4) Uani d 0.9363(14) A 1
H H6 -0.4295 0.0784 -0.0841 0.023 Uiso calc 0.9363(14) A 1
C C7 -0.2218(2) 0.19944(19) 0.11543(18) 0.0186(4) Uani d 0.9363(14) A 1
H H7 -0.2742 0.1591 0.1624 0.022 Uiso calc 0.9363(14) A 1
C C8 -0.0508(2) 0.3086(2) 0.19147(18) 0.0161(3) Uani d 0.9363(14) A 1
C C1' 0.269(8) 0.522(7) 0.368(2) 0.0145(4) Uani d 0.0637(14) A 2
S S1' 0.2341(9) 0.5088(7) 0.2013(7) 0.0176(3) Uani d 0.0637(14) A 2
C C2' 0.134(3) 0.418(2) 0.3485(19) 0.01741(12) Uani d 0.0637(14) A 2
H H2' 0.1347 0.3980 0.4251 0.021 Uiso calc 0.0637(14) A 2
C C3' -0.013(4) 0.335(4) 0.207(2) 0.0161(3) Uani d 0.0637(14) A 2
C C4' -0.173(3) 0.221(3) 0.150(3) 0.0186(4) Uani d 0.0637(14) A 2
H H4' -0.1949 0.1828 0.2106 0.022 Uiso calc 0.0637(14) A 2
C C5' -0.297(4) 0.162(3) 0.013(3) 0.0195(4) Uani d 0.0637(14) A 2
H H5' -0.4184 0.1070 -0.0167 0.023 Uiso calc 0.0637(14) A 2
C C6' -0.248(4) 0.183(3) -0.086(3) 0.0210(4) Uani d 0.0637(14) A 2
H H6' -0.3283 0.1303 -0.1851 0.025 Uiso calc 0.0637(14) A 2
C C7' -0.079(4) 0.284(3) -0.036(3) 0.0203(4) Uani d 0.0637(14) A 2
H H7' -0.0314 0.2892 -0.0985 0.024 Uiso calc 0.0637(14) A 2
C C8' 0.020(4) 0.377(5) 0.108(2) 0.0164(4) Uani d 0.0637(14) A 2
C C9 0.40890(17) 0.61277(13) 0.49233(13) 0.0147(2) Uani d 1 . .
C C10 0.55623(17) 0.72729(13) 0.52005(13) 0.0146(2) Uani d 1 . .
C C11 0.61431(17) 0.77268(13) 0.42743(13) 0.0152(3) Uani d 1 . .
C C12 0.65731(17) 0.91063(13) 0.44855(13) 0.0166(3) Uani d 1 . .
H H12 0.6472 0.9730 0.5204 0.020 Uiso calc 1 . .
C C13 0.71519(17) 0.95607(13) 0.36342(14) 0.0168(3) Uani d 1 . .
C C14 0.72907(16) 0.86471(13) 0.25757(13) 0.0152(3) Uani d 1 . .
C C15 0.69315(17) 0.72810(13) 0.24151(13) 0.0157(3) Uani d 1 . .
C C16 0.63395(17) 0.68128(13) 0.32534(13) 0.0158(3) Uani d 1 . .
H H16 0.6073 0.5881 0.3131 0.019 Uiso calc 1 . .
C C17 0.8251(2) 1.19553(14) 0.51199(15) 0.0231(3) Uani d 1 . .
H H17A 0.7287 1.1871 0.5366 0.035 Uiso calc 1 . .
H H17B 0.8707 1.2866 0.5122 0.035 Uiso calc 1 . .
H H17C 0.9222 1.1864 0.5817 0.035 Uiso calc 1 . .
C C18 0.96108(18) 0.98269(14) 0.22249(14) 0.0202(3) Uani d 1 . .
H H18A 1.0093 1.0624 0.3134 0.030 Uiso calc 1 . .
H H18B 0.9813 1.0158 0.1555 0.030 Uiso calc 1 . .
H H18C 1.0214 0.9217 0.2368 0.030 Uiso calc 1 . .
C C19 0.7008(2) 0.51278(14) 0.13104(16) 0.0231(3) Uani d 1 . .
H H19A 0.7781 0.5191 0.2233 0.035 Uiso calc 1 . .
H H19B 0.7324 0.4680 0.0608 0.035 Uiso calc 1 . .
H H19C 0.5754 0.4577 0.1010 0.035 Uiso calc 1 . .
C C20 0.63205(18) 0.78558(14) 0.86407(13) 0.0185(3) Uani d 1 . .
H H20A 0.7016 0.7356 0.8977 0.028 Uiso calc 1 . .
H H20B 0.5314 0.7673 0.8838 0.028 Uiso calc 1 . .
H H20C 0.7089 0.8856 0.9131 0.028 Uiso calc 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 0.0016 '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'
S S 0.1246 0.1234 '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
N2 N1 C9 103.78(10) ?
N1 N2 N3 115.92(10) y
N1 N2 C20 122.69(11) ?
N3 N2 C20 121.27(11) ?
N2 N3 C10 104.04(10) ?
C13 O1 C17 116.24(10) ?
C14 O2 C18 113.82(10) ?
C15 O3 C19 116.41(10) ?
C2 C1 C9 129.94(17) y
C2 C1 S1 112.33(14) ?
C9 C1 S1 117.55(13) ?
C8 S1 C1 91.33(8) y
C1 C2 C3 113.73(19) ?
C1 C2 H2 123.1 ?
C3 C2 H2 123.1 ?
C8 C3 C4 118.66(16) ?
C8 C3 C2 111.50(15) ?
C4 C3 C2 129.79(17) y
C5 C4 C3 119.15(16) ?
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
C4 C5 C6 121.14(16) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C7 C6 C5 120.88(16) ?
C7 C6 H6 119.6 ?
C5 C6 H6 119.6 ?
C6 C7 C8 118.04(16) ?
C6 C7 H7 121.0 ?
C8 C7 H7 121.0 ?
C7 C8 C3 122.13(15) ?
C7 C8 S1 126.75(13) ?
C3 C8 S1 111.11(11) ?
C2' C1' C9 124.6(18) ?
C2' C1' S1' 107.3(15) ?
C9 C1' S1' 128.0(18) y
C8' S1' C1' 95.8(12) y
C1' C2' C3' 117.3(18) ?
C1' C2' H2' 121.4 ?
C3' C2' H2' 121.4 ?
C4' C3' C8' 115.8(17) ?
C4' C3' C2' 132(2) y
C8' C3' C2' 111.8(16) ?
C5' C4' C3' 122(2) ?
C5' C4' H4' 118.9 ?
C3' C4' H4' 118.9 ?
C4' C5' C6' 120(2) ?
C4' C5' H5' 120.2 ?
C6' C5' H5' 120.2 ?
C7' C6' C5' 118(2) ?
C7' C6' H6' 121.0 ?
C5' C6' H6' 121.0 ?
C6' C7' C8' 118(2) ?
C6' C7' H7' 120.8 ?
C8' C7' H7' 120.8 ?
C7' C8' C3' 119(2) ?
C7' C8' S1' 129(2) y
C3' C8' S1' 106.9(14) ?
C1' C9 N1 123.7(13) ?
C1' C9 C10 127.3(11) y
N1 C9 C10 108.26(11) ?
N1 C9 C1 118.94(13) ?
C10 C9 C1 132.41(13) y
N3 C10 C9 108.00(11) ?
N3 C10 C11 119.08(11) ?
C9 C10 C11 132.90(12) y
C16 C11 C12 120.79(11) ?
C16 C11 C10 120.52(11) ?
C12 C11 C10 118.61(11) ?
C13 C12 C11 119.45(12) ?
C13 C12 H12 120.3 ?
C11 C12 H12 120.3 ?
O1 C13 C14 116.02(11) ?
O1 C13 C12 123.56(12) ?
C14 C13 C12 120.40(12) ?
O2 C14 C13 120.25(11) ?
O2 C14 C15 120.12(11) ?
C13 C14 C15 119.60(11) ?
O3 C15 C16 124.29(12) ?
O3 C15 C14 115.29(11) ?
C16 C15 C14 120.40(12) ?
C15 C16 C11 119.24(12) ?
C15 C16 H16 120.4 ?
C11 C16 H16 120.4 ?
O1 C17 H17A 109.5 ?
O1 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O1 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
O2 C18 H18A 109.5 ?
O2 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O2 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
O3 C19 H19A 109.5 ?
O3 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
O3 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
N2 C20 H20A 109.5 ?
N2 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
N2 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 1.3266(15) y
N1 C9 1.3477(16) y
N2 N3 1.3279(15) y
N2 C20 1.4527(16) y
N3 C10 1.3450(16) y
O1 C13 1.3720(15) ?
O1 C17 1.4210(17) ?
O2 C14 1.3721(14) ?
O2 C18 1.4398(16) ?
O3 C15 1.3666(15) ?
O3 C19 1.4340(16) ?
C1 C2 1.347(3) ?
C1 C9 1.466(2) ?
C1 S1 1.742(2) ?
S1 C8 1.7380(17) ?
C2 C3 1.429(2) ?
C2 H2 0.9500 ?
C3 C8 1.409(2) ?
C3 C4 1.410(2) ?
C4 C5 1.384(2) ?
C4 H4 0.9500 ?
C5 C6 1.404(2) ?
C5 H5 0.9500 ?
C6 C7 1.383(2) ?
C6 H6 0.9500 ?
C7 C8 1.397(2) ?
C7 H7 0.9500 ?
C1' C2' 1.318(19) ?
C1' C9 1.32(2) ?
C1' S1' 1.74(2) ?
S1' C8' 1.731(18) ?
C2' C3' 1.439(17) ?
C2' H2' 0.9500 ?
C3' C4' 1.383(17) ?
C3' C8' 1.413(17) ?
C4' C5' 1.346(17) ?
C4' H4' 0.9500 ?
C5' C6' 1.393(18) ?
C5' H5' 0.9500 ?
C6' C7' 1.385(18) ?
C6' H6' 0.9500 ?
C7' C8' 1.405(18) ?
C7' H7' 0.9500 ?
C9 C10 1.4122(17) ?
C10 C11 1.4723(17) ?
C11 C16 1.3943(18) ?
C11 C12 1.3956(18) ?
C12 C13 1.3930(18) ?
C12 H12 0.9500 ?
C13 C14 1.3911(18) ?
C14 C15 1.4018(18) ?
C15 C16 1.3926(17) ?
C16 H16 0.9500 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C18 H18A 0.9800 ?
C18 H18B 0.9800 ?
C18 H18C 0.9800 ?
C19 H19A 0.9800 ?
C19 H19B 0.9800 ?
C19 H19C 0.9800 ?
C20 H20A 0.9800 ?
C20 H20B 0.9800 ?
C20 H20C 0.9800 ?
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
C9 N1 N2 N3 -0.21(14)
C9 N1 N2 C20 -176.39(11)
N1 N2 N3 C10 -0.26(14)
C20 N2 N3 C10 175.99(11)
C2 C1 S1 C8 0.6(4)
C9 C1 S1 C8 176.2(4)
C9 C1 C2 C3 -175.7(5)
S1 C1 C2 C3 -0.7(5)
C1 C2 C3 C8 0.5(4)
C1 C2 C3 C4 177.8(4)
C8 C3 C4 C5 0.0(4)
C2 C3 C4 C5 -177.2(3)
C3 C4 C5 C6 -0.4(3)
C4 C5 C6 C7 0.1(3)
C5 C6 C7 C8 0.6(3)
C6 C7 C8 C3 -1.1(4)
C6 C7 C8 S1 177.16(19)
C4 C3 C8 C7 0.8(4)
C2 C3 C8 C7 178.4(2)
C4 C3 C8 S1 -177.7(2)
C2 C3 C8 S1 -0.1(3)
C1 S1 C8 C7 -178.7(3)
C1 S1 C8 C3 -0.3(3)
C2' C1' S1' C8' 9(7)
C9 C1' S1' C8' -176(9)
C9 C1' C2' C3' 175(7)
S1' C1' C2' C3' -8(8)
C1' C2' C3' C4' -180(7)
C1' C2' C3' C8' 4(8)
C8' C3' C4' C5' -7(7)
C2' C3' C4' C5' 177(4)
C3' C4' C5' C6' 21(6)
C4' C5' C6' C7' -11(6)
C5' C6' C7' C8' -12(7)
C6' C7' C8' C3' 27(8)
C6' C7' C8' S1' 178(4)
C4' C3' C8' C7' -17(8)
C2' C3' C8' C7' 160(5)
C4' C3' C8' S1' -174(4)
C2' C3' C8' S1' 3(6)
C1' S1' C8' C7' -160(6)
C1' S1' C8' C3' -6(6)
C2' C1' C9 N1 -10(12)
S1' C1' C9 N1 174(5)
C2' C1' C9 C10 -179(6)
S1' C1' C9 C10 6(12)
S1' C1' C9 C1 -16E1(6)
N2 N1 C9 C1' -170(6)
N2 N1 C9 C10 0.57(13)
N2 N1 C9 C1 -173.1(3)
S1 C1 C9 C1' -15E1(5)
C2 C1 C9 N1 173.7(5)
S1 C1 C9 N1 -1.1(5)
C2 C1 C9 C10 1.8(8)
S1 C1 C9 C10 -172.95(18)
N2 N3 C10 C9 0.60(13)
N2 N3 C10 C11 179.11(11)
C1' C9 C10 N3 170(6)
N1 C9 C10 N3 -0.76(14)
C1 C9 C10 N3 171.7(4)
C1' C9 C10 C11 -9(6)
N1 C9 C10 C11 -178.99(13)
C1 C9 C10 C11 -6.5(4)
N3 C10 C11 C16 129.29(13)
C9 C10 C11 C16 -52.6(2)
N3 C10 C11 C12 -47.72(17)
C9 C10 C11 C12 130.36(15)
C16 C11 C12 C13 2.02(19)
C10 C11 C12 C13 179.01(12)
C17 O1 C13 C14 -151.61(12)
C17 O1 C13 C12 29.78(18)
C11 C12 C13 O1 178.95(12)
C11 C12 C13 C14 0.40(19)
C18 O2 C14 C13 82.87(15)
C18 O2 C14 C15 -99.29(14)
O1 C13 C14 O2 -4.02(18)
C12 C13 C14 O2 174.63(11)
O1 C13 C14 C15 178.13(11)
C12 C13 C14 C15 -3.22(19)
C19 O3 C15 C16 -2.60(18)
C19 O3 C15 C14 175.84(11)
O2 C14 C15 O3 7.32(17)
C13 C14 C15 O3 -174.83(11)
O2 C14 C15 C16 -174.18(11)
C13 C14 C15 C16 3.68(19)
O3 C15 C16 C11 177.06(12)
C14 C15 C16 C11 -1.30(19)
C12 C11 C16 C15 -1.56(19)
C10 C11 C16 C15 -178.49(12)
