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#$Date: 2024-01-06 10:32:04 +0100 (Sat 06 de Jan de 2024) $
#$Revision: 288879 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/96/7159645.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_7159645
loop_
_publ_author_name
'Kamińska, Karolina'
'Iwan, Dominika'
'Trojnar, Jakub'
'Daszkiewicz, Marek'
'Rode, Joanna E.'
'Wojaczyński, Jacek'
'Wojaczyńska, Elżbieta'
_publ_section_title
;
 Rearrangement of thiazolidine derivatives - a synthesis of a chiral fused
 oxathiane-γ-lactam bicyclic system.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9182
_journal_page_last               9191
_journal_paper_doi               10.1039/d3ob01454a
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C9 H15 N O2 S'
_chemical_formula_sum            'C9 H15 N O2 S'
_chemical_formula_weight         201.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2c6ffg
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.918(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.872(3)
_cell_length_b                   6.6196(7)
_cell_length_c                   16.260(2)
_cell_measurement_reflns_used    1176
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.7960
_cell_measurement_theta_min      3.6620
_cell_volume                     2023.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.6249
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5194
_diffrn_reflns_point_group_measured_fraction_full 0.780
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.726
_diffrn_reflns_theta_min         2.648
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0103(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0752
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0830P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.2078
_reflns_Friedel_coverage         0.382
_reflns_Friedel_fraction_full    0.515
_reflns_Friedel_fraction_max     0.454
_reflns_number_gt                1916
_reflns_number_total             3217
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01454a2.cif
_cod_data_source_block           EWKK21-016kr1
_cod_depositor_comments
'Adding full bibliography for 7159641--7159650.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7159645
_shelx_shelxl_version_number     2018/3
_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   0.857
_shelx_estimated_absorpt_t_max   0.991
_oxdiff_exptl_absorpt_empirical_full_min 0.475
_oxdiff_exptl_absorpt_empirical_full_max 16.455
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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 0.39840(13) 0.4922(4) 0.41311(16) 0.0647(7) Uani 1 1 d . . . . .
O1 O 0.2817(3) 0.0030(9) 0.5137(4) 0.0561(15) Uani 1 1 d . . . . .
O2 O 0.3277(3) 0.5437(10) 0.6442(4) 0.0639(17) Uani 1 1 d . . . . .
H2O2 H 0.296679 0.537851 0.596530 0.096 Uiso 1 1 calc R U . . .
N1 N 0.3642(3) 0.2437(10) 0.5150(4) 0.0521(17) Uani 1 1 d . . . . .
C1 C 0.3552(4) 0.2570(14) 0.4218(5) 0.053(2) Uani 1 1 d . . . . .
H1 H 0.304464 0.266083 0.388426 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4082(5) 0.3945(12) 0.5724(6) 0.053(2) Uani 1 1 d . . . . .
H2 H 0.458005 0.351069 0.591810 0.064 Uiso 1 1 calc R U . . .
C3 C 0.3996(5) 0.5848(14) 0.5177(6) 0.060(2) Uani 1 1 d . . . . .
H3A H 0.439184 0.676564 0.541930 0.072 Uiso 1 1 calc R U . . .
H3B H 0.355631 0.653991 0.513491 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3267(4) 0.1272(12) 0.5511(5) 0.0474(19) Uani 1 1 d . . . . .
C5 C 0.3513(4) 0.1760(13) 0.6492(5) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.3789(4) 0.3925(14) 0.6498(5) 0.054(2) Uani 1 1 d . . . . .
H6 H 0.418724 0.412703 0.703644 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3868(6) 0.0831(16) 0.3906(6) 0.076(3) Uani 1 1 d . . . . .
H7A H 0.359955 -0.036654 0.392120 0.114 Uiso 1 1 calc R U . . .
H7B H 0.435115 0.065047 0.427440 0.114 Uiso 1 1 calc R U . . .
H7C H 0.385855 0.107814 0.332101 0.114 Uiso 1 1 calc R U . . .
C8 C 0.4130(5) 0.0327(15) 0.6913(6) 0.064(2) Uani 1 1 d . . . . .
H8A H 0.433680 0.065570 0.751823 0.095 Uiso 1 1 calc R U . . .
H8B H 0.448385 0.046373 0.663072 0.095 Uiso 1 1 calc R U . . .
H8C H 0.395915 -0.103875 0.685571 0.095 Uiso 1 1 calc R U . . .
C9 C 0.2927(5) 0.1511(15) 0.6873(6) 0.065(3) Uani 1 1 d . . . . .
H9A H 0.309471 0.189366 0.747479 0.098 Uiso 1 1 calc R U . . .
H9B H 0.277665 0.012511 0.682348 0.098 Uiso 1 1 calc R U . . .
H9C H 0.253249 0.235449 0.656511 0.098 Uiso 1 1 calc R U . . .
S2 S 0.42122(14) 0.3438(4) 0.18797(16) 0.0714(8) Uani 1 1 d . . . . .
O3 O 0.2796(3) 0.8141(9) 0.0034(4) 0.0607(16) Uani 1 1 d . . . . .
O4 O 0.3160(4) 0.2704(10) -0.0935(4) 0.0716(18) Uani 1 1 d . . . . .
H4O4 H 0.285462 0.292991 -0.070724 0.107 Uiso 1 1 calc DR U . . .
N2 N 0.3675(4) 0.5819(10) 0.0572(4) 0.0521(18) Uani 1 1 d . . . . .
C10 C 0.3713(5) 0.5751(13) 0.1481(5) 0.056(2) Uani 1 1 d . . . . .
H10 H 0.323394 0.564564 0.152433 0.067 Uiso 1 1 calc R U . . .
C11 C 0.4082(5) 0.4353(13) 0.0263(5) 0.054(2) Uani 1 1 d . . . . .
H11 H 0.456672 0.484733 0.036125 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4095(5) 0.2480(14) 0.0804(6) 0.065(2) Uani 1 1 d . . . . .
H12A H 0.448507 0.159802 0.080648 0.079 Uiso 1 1 calc R U . . .
H12B H 0.365179 0.173628 0.058229 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3215(4) 0.6929(14) -0.0065(5) 0.051(2) Uani 1 1 d . . . . .
C14 C 0.3362(5) 0.6413(13) -0.0897(5) 0.052(2) Uani 1 1 d . . . . .
C15 C 0.3675(5) 0.4243(13) -0.0710(6) 0.057(2) Uani 1 1 d . . . . .
H15 H 0.401359 0.403330 -0.102579 0.069 Uiso 1 1 calc R U . . .
C16 C 0.4095(7) 0.7543(18) 0.1993(6) 0.093(4) Uani 1 1 d . . . . .
H16A H 0.383004 0.875027 0.177482 0.139 Uiso 1 1 calc R U . . .
H16B H 0.456011 0.764921 0.193690 0.139 Uiso 1 1 calc R U . . .
H16C H 0.413919 0.737050 0.259464 0.139 Uiso 1 1 calc R U . . .
C17 C 0.3914(5) 0.7872(18) -0.1019(6) 0.074(3) Uani 1 1 d . . . . .
H17A H 0.400875 0.755057 -0.154665 0.111 Uiso 1 1 calc R U . . .
H17B H 0.434578 0.775669 -0.053524 0.111 Uiso 1 1 calc R U . . .
H17C H 0.373718 0.922879 -0.105079 0.111 Uiso 1 1 calc R U . . .
C18 C 0.2680(5) 0.6529(18) -0.1680(6) 0.078(3) Uani 1 1 d . . . . .
H18A H 0.277867 0.610126 -0.219374 0.118 Uiso 1 1 calc R U . . .
H18B H 0.250909 0.789554 -0.175392 0.118 Uiso 1 1 calc R U . . .
H18C H 0.232535 0.566379 -0.158397 0.118 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 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 94.7(4) . . ?
C6 O2 H2O2 109.5 . . ?
C4 N1 C2 114.9(7) . . ?
C4 N1 C1 126.2(7) . . ?
C2 N1 C1 117.9(6) . . ?
N1 C1 C7 112.6(8) . . ?
N1 C1 S1 103.3(5) . . ?
C7 C1 S1 112.3(6) . . ?
N1 C1 H1 109.5 . . ?
C7 C1 H1 109.5 . . ?
S1 C1 H1 109.5 . . ?
N1 C2 C3 105.4(7) . . ?
N1 C2 C6 102.1(6) . . ?
C3 C2 C6 118.9(7) . . ?
N1 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C6 C2 H2 110.0 . . ?
C2 C3 S1 103.6(6) . . ?
C2 C3 H3A 111.0 . . ?
S1 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
S1 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O1 C4 N1 126.4(8) . . ?
O1 C4 C5 126.2(7) . . ?
N1 C4 C5 107.4(7) . . ?
C9 C5 C8 111.5(7) . . ?
C9 C5 C6 115.2(7) . . ?
C8 C5 C6 110.1(7) . . ?
C9 C5 C4 112.2(7) . . ?
C8 C5 C4 105.8(7) . . ?
C6 C5 C4 101.3(6) . . ?
O2 C6 C5 114.4(6) . . ?
O2 C6 C2 113.2(7) . . ?
C5 C6 C2 103.3(7) . . ?
O2 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
C2 C6 H6 108.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 S2 C10 93.8(4) . . ?
C15 O4 H4O4 109.5 . . ?
C13 N2 C11 114.3(6) . . ?
C13 N2 C10 126.4(7) . . ?
C11 N2 C10 118.6(6) . . ?
N2 C10 C16 112.9(7) . . ?
N2 C10 S2 103.3(6) . . ?
C16 C10 S2 110.2(6) . . ?
N2 C10 H10 110.1 . . ?
C16 C10 H10 110.1 . . ?
S2 C10 H10 110.1 . . ?
N2 C11 C12 104.6(7) . . ?
N2 C11 C15 102.8(6) . . ?
C12 C11 C15 117.8(8) . . ?
N2 C11 H11 110.4 . . ?
C12 C11 H11 110.4 . . ?
C15 C11 H11 110.4 . . ?
C11 C12 S2 104.4(6) . . ?
C11 C12 H12A 110.9 . . ?
S2 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
S2 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
O3 C13 N2 125.6(8) . . ?
O3 C13 C14 127.8(8) . . ?
N2 C13 C14 106.5(7) . . ?
C13 C14 C17 109.2(8) . . ?
C13 C14 C18 110.9(7) . . ?
C17 C14 C18 110.0(8) . . ?
C13 C14 C15 102.3(7) . . ?
C17 C14 C15 110.6(7) . . ?
C18 C14 C15 113.5(8) . . ?
O4 C15 C11 113.6(7) . . ?
O4 C15 C14 114.0(7) . . ?
C11 C15 C14 101.7(7) . . ?
O4 C15 H15 109.1 . . ?
C11 C15 H15 109.1 . . ?
C14 C15 H15 109.1 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C3 1.800(9) . ?
S1 C1 1.806(9) . ?
O1 C4 1.221(9) . ?
O2 C6 1.410(10) . ?
O2 H2O2 0.8200 . ?
N1 C4 1.333(10) . ?
N1 C2 1.450(11) . ?
N1 C1 1.470(10) . ?
C1 C7 1.477(13) . ?
C1 H1 0.9800 . ?
C2 C3 1.520(12) . ?
C2 C6 1.549(11) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.543(11) . ?
C5 C9 1.495(11) . ?
C5 C8 1.527(12) . ?
C5 C6 1.533(11) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
S2 C12 1.803(9) . ?
S2 C10 1.825(9) . ?
O3 C13 1.205(10) . ?
O4 C15 1.406(11) . ?
O4 H4O4 0.8200 . ?
N2 C13 1.354(10) . ?
N2 C11 1.454(10) . ?
N2 C10 1.456(9) . ?
C10 C16 1.506(13) . ?
C10 H10 0.9800 . ?
C11 C12 1.516(12) . ?
C11 C15 1.526(11) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(11) . ?
C14 C17 1.522(13) . ?
C14 C18 1.531(12) . ?
C14 C15 1.556(12) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
_geom_hbond_publ_flag
O2 H2O2 O1 0.82 1.97 2.788(8) 174.7 4_556 yes
O4 H4O4 O3 0.82 1.95 2.764(8) 171.0 4_545 yes
C2 H2 S1 0.98 3.03 3.829(9) 139.8 2_656 yes
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
C4 N1 C1 C7 -77.1(10) . . . . ?
C2 N1 C1 C7 114.8(9) . . . . ?
C4 N1 C1 S1 161.5(7) . . . . ?
C2 N1 C1 S1 -6.6(8) . . . . ?
C3 S1 C1 N1 -16.0(6) . . . . ?
C3 S1 C1 C7 -137.6(7) . . . . ?
C4 N1 C2 C3 -138.4(7) . . . . ?
C1 N1 C2 C3 31.0(10) . . . . ?
C4 N1 C2 C6 -13.5(9) . . . . ?
C1 N1 C2 C6 155.9(7) . . . . ?
N1 C2 C3 S1 -39.3(8) . . . . ?
C6 C2 C3 S1 -152.9(6) . . . . ?
C1 S1 C3 C2 32.8(7) . . . . ?
C2 N1 C4 O1 173.2(8) . . . . ?
C1 N1 C4 O1 4.9(13) . . . . ?
C2 N1 C4 C5 -7.5(9) . . . . ?
C1 N1 C4 C5 -175.9(7) . . . . ?
O1 C4 C5 C9 -32.1(11) . . . . ?
N1 C4 C5 C9 148.7(7) . . . . ?
O1 C4 C5 C8 89.7(9) . . . . ?
N1 C4 C5 C8 -89.5(8) . . . . ?
O1 C4 C5 C6 -155.4(8) . . . . ?
N1 C4 C5 C6 25.3(8) . . . . ?
C9 C5 C6 O2 -29.9(10) . . . . ?
C8 C5 C6 O2 -157.0(7) . . . . ?
C4 C5 C6 O2 91.3(8) . . . . ?
C9 C5 C6 C2 -153.5(7) . . . . ?
C8 C5 C6 C2 79.4(8) . . . . ?
C4 C5 C6 C2 -32.2(8) . . . . ?
N1 C2 C6 O2 -95.9(8) . . . . ?
C3 C2 C6 O2 19.5(11) . . . . ?
N1 C2 C6 C5 28.5(8) . . . . ?
C3 C2 C6 C5 143.8(8) . . . . ?
C13 N2 C10 C16 -79.1(11) . . . . ?
C11 N2 C10 C16 111.3(9) . . . . ?
C13 N2 C10 S2 161.9(7) . . . . ?
C11 N2 C10 S2 -7.7(8) . . . . ?
C12 S2 C10 N2 -15.3(6) . . . . ?
C12 S2 C10 C16 -136.1(7) . . . . ?
C13 N2 C11 C12 -138.9(7) . . . . ?
C10 N2 C11 C12 32.0(10) . . . . ?
C13 N2 C11 C15 -15.3(9) . . . . ?
C10 N2 C11 C15 155.6(7) . . . . ?
N2 C11 C12 S2 -39.7(8) . . . . ?
C15 C11 C12 S2 -153.1(7) . . . . ?
C10 S2 C12 C11 32.7(7) . . . . ?
C11 N2 C13 O3 175.3(8) . . . . ?
C10 N2 C13 O3 5.3(14) . . . . ?
C11 N2 C13 C14 -7.4(9) . . . . ?
C10 N2 C13 C14 -177.4(7) . . . . ?
O3 C13 C14 C17 86.3(10) . . . . ?
N2 C13 C14 C17 -90.9(8) . . . . ?
O3 C13 C14 C18 -35.0(12) . . . . ?
N2 C13 C14 C18 147.8(8) . . . . ?
O3 C13 C14 C15 -156.4(9) . . . . ?
N2 C13 C14 C15 26.4(8) . . . . ?
N2 C11 C15 O4 -92.9(8) . . . . ?
C12 C11 C15 O4 21.4(11) . . . . ?
N2 C11 C15 C14 30.1(8) . . . . ?
C12 C11 C15 C14 144.4(8) . . . . ?
C13 C14 C15 O4 88.3(8) . . . . ?
C17 C14 C15 O4 -155.4(7) . . . . ?
C18 C14 C15 O4 -31.3(10) . . . . ?
C13 C14 C15 C11 -34.4(8) . . . . ?
C17 C14 C15 C11 81.9(9) . . . . ?
C18 C14 C15 C11 -154.0(7) . . . . ?
