#------------------------------------------------------------------------------
#$Date: 2020-11-20 00:26:25 +0200 (Fri, 20 Nov 2020) $
#$Revision: 259188 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518242.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_4518242
loop_
_publ_author_name
'Uno, Hiroto'
'Kawai, Koki'
'Shiro, Motoo'
'Shibata, Norio'
_publ_section_title
;
 Modular Synthesis of Medium-Sized Fluorinated and Nonfluorinated
 Heterocyclic Lactones by Sequential CN-Bond-Cleaving Ring Expansion under
 Pd Catalysis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14117
_journal_page_last               14126
_journal_paper_doi               10.1021/acscatal.0c03927
_journal_year                    2020
_chemical_formula_moiety         'C25 H20 F N O5 S'
_chemical_formula_sum            'C25 H20 F N O5 S'
_chemical_formula_weight         465.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.835(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   16.6287(10)
_cell_length_b                   9.5046(5)
_cell_length_c                   14.4444(8)
_cell_measurement_reflns_used    12014
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.51
_cell_volume                     2147.5(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20122
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.449
_diffrn_reflns_theta_min         2.508
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0274P)²+1.2991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2904
_reflns_number_total             4912
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cs0c03927_si_007.cif
_cod_data_source_block           MS065
_cod_database_code               4518242
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68869(5) 0.23970(8) 0.96817(6) 0.0411(2) Uani 1 1 d . . . . .
F1A F 0.88012(15) -0.2093(2) 0.72321(15) 0.0488(8) Uani 0.772(4) 1 d . . P A 1
F1B F 0.6438(5) -0.1375(7) 0.8152(6) 0.050(3) Uani 0.228(4) 1 d . . P A 2
O1 O 0.93147(14) 0.1348(2) 1.18237(14) 0.0529(6) Uani 1 1 d . . . . .
O2 O 0.86095(15) -0.0535(2) 1.02453(15) 0.0520(6) Uani 1 1 d . . . . .
O3 O 0.91233(12) 0.10298(19) 0.94179(13) 0.0379(5) Uani 1 1 d . . . . .
O4 O 0.72491(14) 0.2151(2) 1.07169(15) 0.0500(6) Uani 1 1 d . . . . .
O5 O 0.63514(13) 0.1363(2) 0.90451(16) 0.0543(6) Uani 1 1 d . . . . .
N1 N 0.77059(14) 0.2637(2) 0.92989(15) 0.0331(5) Uani 1 1 d . . . . .
C1 C 0.89827(18) 0.3237(3) 1.06758(19) 0.0334(7) Uani 1 1 d . . . . .
C2 C 0.95734(19) 0.4212(3) 1.1225(2) 0.0383(7) Uani 1 1 d . . . . .
H2 H 1.000687 0.393159 1.181664 0.046 Uiso 1 1 calc R U . . .
C3 C 0.9531(2) 0.5590(3) 1.0912(2) 0.0432(8) Uani 1 1 d . . . . .
H3 H 0.993587 0.625792 1.128612 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8899(2) 0.5996(3) 1.0056(2) 0.0423(8) Uani 1 1 d . . . . .
H4 H 0.887916 0.694177 0.983615 0.051 Uiso 1 1 calc R U . . .
C5 C 0.82944(19) 0.5040(3) 0.9513(2) 0.0385(7) Uani 1 1 d . . . . .
H5 H 0.785469 0.533065 0.893005 0.046 Uiso 1 1 calc R U . . .
C6 C 0.83349(18) 0.3662(3) 0.98256(19) 0.0319(7) Uani 1 1 d . . . . .
C7 C 0.90684(18) 0.1738(3) 1.0975(2) 0.0379(7) Uani 1 1 d . . . . .
C8 C 0.88885(18) 0.0600(3) 1.0171(2) 0.0363(7) Uani 1 1 d . . . . .
C9 C 0.89170(19) 0.0037(3) 0.8597(2) 0.0432(8) Uani 1 1 d . . . . .
H9A H 0.915590 -0.089706 0.884854 0.052 Uiso 1 1 calc R U . . .
H9B H 0.919176 0.035554 0.812354 0.052 Uiso 1 1 calc R U . . .
C10 C 0.79649(18) -0.0105(3) 0.80665(19) 0.0357(7) Uani 1 1 d . . . . .
C11 C 0.74131(19) 0.0962(3) 0.7900(2) 0.0391(7) Uani 1 1 d . . . . .
H11 H 0.683761 0.074377 0.752202 0.047 Uiso 1 1 calc R U . . .
C12 C 0.75818(18) 0.2460(3) 0.82307(19) 0.0384(7) Uani 1 1 d . . . . .
H12A H 0.809973 0.279467 0.810615 0.046 Uiso 1 1 calc R U . . .
H12B H 0.709503 0.305048 0.783786 0.046 Uiso 1 1 calc R U . . .
C13 C 0.76342(19) -0.1525(3) 0.77124(19) 0.0354(7) Uani 1 1 d . . . . .
C14 C 0.8049(2) -0.2439(3) 0.7280(2) 0.0429(7) Uani 1 1 d . . . . .
H14 H 0.859327 -0.217059 0.726019 0.052 Uiso 0.228(4) 1 calc R U P A 2
C15 C 0.7718(2) -0.3720(3) 0.6874(2) 0.0511(9) Uani 1 1 d . . . . .
H15 H 0.802751 -0.430732 0.658144 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6940(2) -0.4127(3) 0.6902(2) 0.0516(9) Uani 1 1 d . . . . .
H16 H 0.669578 -0.499263 0.661047 0.062 Uiso 1 1 calc R U . . .
C17 C 0.6517(2) -0.3297(3) 0.7344(2) 0.0495(9) Uani 1 1 d . . . . .
H17 H 0.598027 -0.359130 0.737330 0.059 Uiso 1 1 calc R U . . .
C18 C 0.6860(2) -0.2026(3) 0.7752(2) 0.0410(8) Uani 1 1 d . . . . .
H18 H 0.655661 -0.147228 0.807156 0.049 Uiso 0.772(4) 1 calc R U P A 1
C19 C 0.63140(18) 0.3986(3) 0.9515(2) 0.0358(7) Uani 1 1 d . . . . .
C20 C 0.55760(19) 0.4154(3) 0.8716(2) 0.0465(8) Uani 1 1 d . . . . .
H20 H 0.536800 0.341016 0.825724 0.056 Uiso 1 1 calc R U . . .
C21 C 0.5143(2) 0.5421(4) 0.8593(2) 0.0516(9) Uani 1 1 d . . . . .
H21 H 0.463486 0.553652 0.804263 0.062 Uiso 1 1 calc R U . . .
C22 C 0.54256(19) 0.6517(3) 0.9243(2) 0.0439(8) Uani 1 1 d . . . . .
C23 C 0.6173(2) 0.6325(3) 1.0040(2) 0.0496(8) Uani 1 1 d . . . . .
H23 H 0.638530 0.707366 1.049313 0.060 Uiso 1 1 calc R U . . .
C24 C 0.6611(2) 0.5063(3) 1.0184(2) 0.0453(8) Uani 1 1 d . . . . .
H24 H 0.711410 0.493860 1.074010 0.054 Uiso 1 1 calc R U . . .
C25 C 0.4957(2) 0.7901(3) 0.9106(3) 0.0658(11) Uani 1 1 d . . . . .
H25A H 0.527925 0.861668 0.888956 0.079 Uiso 1 1 calc R U . . .
H25B H 0.489862 0.819257 0.973069 0.079 Uiso 1 1 calc R U . . .
H25C H 0.438840 0.779479 0.860742 0.079 Uiso 1 1 calc R U . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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
O4 S1 O5 120.62(13) . . ?
O4 S1 N1 105.69(12) . . ?
O5 S1 N1 106.50(13) . . ?
O4 S1 C19 107.50(13) . . ?
O5 S1 C19 108.14(13) . . ?
N1 S1 C19 107.79(13) . . ?
C8 O3 C9 114.2(2) . . ?
C6 N1 C12 116.2(2) . . ?
C6 N1 S1 116.73(18) . . ?
C12 N1 S1 119.31(18) . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 C7 119.8(2) . . ?
C6 C1 C7 120.4(2) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 N1 121.5(2) . . ?
C1 C6 N1 118.4(2) . . ?
O1 C7 C1 123.7(3) . . ?
O1 C7 C8 117.4(3) . . ?
C1 C7 C8 118.8(2) . . ?
O2 C8 O3 125.3(3) . . ?
O2 C8 C7 123.3(3) . . ?
O3 C8 C7 111.3(2) . . ?
O3 C9 C10 112.7(2) . . ?
O3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
O3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C13 118.6(3) . . ?
C11 C10 C9 124.1(3) . . ?
C13 C10 C9 117.3(2) . . ?
C10 C11 C12 128.5(3) . . ?
C10 C11 H11 115.7 . . ?
C12 C11 H11 115.7 . . ?
N1 C12 C11 112.4(2) . . ?
N1 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C18 114.4(3) . . ?
C14 C13 C10 123.0(3) . . ?
C18 C13 C10 122.5(3) . . ?
F1A C14 C15 116.5(3) . . ?
F1A C14 C13 119.6(3) . . ?
C15 C14 C13 123.9(3) . . ?
C15 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
F1B C18 C17 115.2(5) . . ?
F1B C18 C13 122.4(4) . . ?
C17 C18 C13 122.4(3) . . ?
C17 C18 H18 118.8 . . ?
C13 C18 H18 118.8 . . ?
C20 C19 C24 120.4(3) . . ?
C20 C19 S1 120.1(2) . . ?
C24 C19 S1 119.5(2) . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 122.0(3) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 117.9(3) . . ?
C21 C22 C25 122.0(3) . . ?
C23 C22 C25 120.0(3) . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C19 C24 C23 119.6(3) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
S1 O4 1.429(2) . ?
S1 O5 1.431(2) . ?
S1 N1 1.650(2) . ?
S1 C19 1.758(3) . ?
F1A C14 1.317(4) . ?
F1B C18 1.218(8) . ?
O1 C7 1.212(3) . ?
O2 C8 1.193(3) . ?
O3 C8 1.338(3) . ?
O3 C9 1.462(3) . ?
N1 C6 1.442(3) . ?
N1 C12 1.495(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.391(3) . ?
C1 C7 1.481(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.540(4) . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.334(4) . ?
C10 C13 1.481(4) . ?
C11 C12 1.498(4) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.384(4) . ?
C13 C18 1.392(4) . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.363(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.353(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.379(4) . ?
C19 C24 1.380(4) . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(4) . ?
C22 C25 1.508(4) . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 N1 C6 -51.5(2) . . . . ?
O5 S1 N1 C6 179.12(18) . . . . ?
C19 S1 N1 C6 63.3(2) . . . . ?
O4 S1 N1 C12 160.35(19) . . . . ?
O5 S1 N1 C12 30.9(2) . . . . ?
C19 S1 N1 C12 -84.9(2) . . . . ?
C6 C1 C2 C3 -1.8(4) . . . . ?
C7 C1 C2 C3 175.5(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C4 C5 C6 N1 178.3(3) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C7 C1 C6 C5 -175.4(3) . . . . ?
C2 C1 C6 N1 -176.9(3) . . . . ?
C7 C1 C6 N1 5.8(4) . . . . ?
C12 N1 C6 C5 55.3(4) . . . . ?
S1 N1 C6 C5 -93.9(3) . . . . ?
C12 N1 C6 C1 -125.9(3) . . . . ?
S1 N1 C6 C1 84.9(3) . . . . ?
C2 C1 C7 O1 36.4(5) . . . . ?
C6 C1 C7 O1 -146.2(3) . . . . ?
C2 C1 C7 C8 -139.7(3) . . . . ?
C6 C1 C7 C8 37.6(4) . . . . ?
C9 O3 C8 O2 7.0(4) . . . . ?
C9 O3 C8 C7 -176.0(2) . . . . ?
O1 C7 C8 O2 34.4(4) . . . . ?
C1 C7 C8 O2 -149.2(3) . . . . ?
O1 C7 C8 O3 -142.6(3) . . . . ?
C1 C7 C8 O3 33.8(4) . . . . ?
C8 O3 C9 C10 67.9(3) . . . . ?
O3 C9 C10 C11 37.8(4) . . . . ?
O3 C9 C10 C13 -142.3(2) . . . . ?
C13 C10 C11 C12 176.3(3) . . . . ?
C9 C10 C11 C12 -3.9(5) . . . . ?
C6 N1 C12 C11 143.3(2) . . . . ?
S1 N1 C12 C11 -68.3(3) . . . . ?
C10 C11 C12 N1 -75.3(4) . . . . ?
C11 C10 C13 C14 138.7(3) . . . . ?
C9 C10 C13 C14 -41.1(4) . . . . ?
C11 C10 C13 C18 -38.6(4) . . . . ?
C9 C10 C13 C18 141.6(3) . . . . ?
C18 C13 C14 F1A -177.8(3) . . . . ?
C10 C13 C14 F1A 4.7(4) . . . . ?
C18 C13 C14 C15 2.9(4) . . . . ?
C10 C13 C14 C15 -174.6(3) . . . . ?
F1A C14 C15 C16 -179.8(3) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C17 -1.7(5) . . . . ?
C15 C16 C17 C18 1.2(5) . . . . ?
C16 C17 C18 F1B -178.4(5) . . . . ?
C16 C17 C18 C13 1.4(5) . . . . ?
C14 C13 C18 F1B 176.5(5) . . . . ?
C10 C13 C18 F1B -6.0(6) . . . . ?
C14 C13 C18 C17 -3.3(4) . . . . ?
C10 C13 C18 C17 174.2(3) . . . . ?
O4 S1 C19 C20 -145.8(2) . . . . ?
O5 S1 C19 C20 -14.1(3) . . . . ?
N1 S1 C19 C20 100.6(3) . . . . ?
O4 S1 C19 C24 34.6(3) . . . . ?
O5 S1 C19 C24 166.3(2) . . . . ?
N1 S1 C19 C24 -79.0(3) . . . . ?
C24 C19 C20 C21 0.5(5) . . . . ?
S1 C19 C20 C21 -179.1(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C23 0.3(5) . . . . ?
C20 C21 C22 C25 179.6(3) . . . . ?
C21 C22 C23 C24 -1.0(5) . . . . ?
C25 C22 C23 C24 179.7(3) . . . . ?
C20 C19 C24 C23 -1.2(5) . . . . ?
S1 C19 C24 C23 178.4(3) . . . . ?
C22 C23 C24 C19 1.5(5) . . . . ?
