#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247722.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_7247722
loop_
_publ_author_name
'Madhesiya, Avinash'
'Dash, Sibananda G.'
'Gupta, Princi'
'Akhir, Abdul'
'Saxena, Deepanshi'
'Maitra, Rahul'
'Chopra, Sidharth'
'Thakur, Tejender S.'
_publ_section_title
;
 Development of new multicomponent crystals of the antifungal drug
 tioconazole and the assessment of their biopharmaceutical attributes
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              6758
_journal_page_last               6776
_journal_paper_doi               10.1039/D3CE00948C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C16 H14 Cl3 N2 O S, C4 H3 O4, O'
_chemical_formula_sum            'C20 H17 Cl3 N2 O6 S'
_chemical_formula_weight         519.77
_chemical_name_common            'Tioconazole-Fumerate salt monohydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                94.572(2)
_cell_angle_beta                 98.318(2)
_cell_angle_gamma                94.709(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4874(2)
_cell_length_b                   8.0833(3)
_cell_length_c                   19.8791(5)
_cell_measurement_reflns_used    13045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9910
_cell_measurement_theta_min      2.2500
_cell_volume                     1181.34(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00   0.00  120
  2  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00  70.00  120
  3  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 140.00  120
  4  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 210.00  120
  5  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 280.00  120
  6  ω   -130.00  50.00   1.00    4.00    --  -40.00   0.00   0.00  180
  7  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00   0.00  120
  8  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00  70.00  120
  9  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00 140.00  120
 10  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00 210.00  120
 11  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00 280.00  120
 12  ω   -160.00  20.00   1.00    4.00    --  -70.00   0.00   0.00  180
 13  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00   0.00  120
 14  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00  70.00  120
 15  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 140.00  120
 16  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 210.00  120
 17  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 280.00  120
 18  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00   0.00  120
 19  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00  70.00  120
 20  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 140.00  120
 21  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 210.00  120
 22  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 280.00  120
 23  ω   -190.00 -10.00   1.00    4.00    -- -100.00   0.00   0.00  180
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23733
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.787
_diffrn_reflns_theta_min         2.256
_diffrn_source                   MicroMax003_Cu
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.330
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.0155(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   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1222P)²+0.5265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3561
_reflns_number_total             4386
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ-FUMH1
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247722
_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   0.250
_shelx_estimated_absorpt_t_max   0.307
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.9293(4) 0.3000(4) 0.35023(15) 0.0470(7) Uani 1 1 d . . . . .
C2 C 0.8351(4) 0.2516(4) 0.40172(16) 0.0504(7) Uani 1 1 d . . . . .
C3 C 0.7687(4) 0.3660(4) 0.44514(16) 0.0555(8) Uani 1 1 d . . . . .
H3 H 0.704483 0.331015 0.478967 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8002(5) 0.5317(4) 0.43691(16) 0.0559(8) Uani 1 1 d . . . . .
C5 C 0.8971(5) 0.5856(4) 0.38817(19) 0.0655(9) Uani 1 1 d . . . . .
H5 H 0.919996 0.698893 0.384167 0.079 Uiso 1 1 calc R U . . .
C6 C 0.9606(5) 0.4685(4) 0.34480(17) 0.0599(8) Uani 1 1 d . . . . .
H6 H 1.025723 0.504528 0.311381 0.072 Uiso 1 1 calc R U . . .
C7 C 0.9892(4) 0.1717(4) 0.30007(15) 0.0489(7) Uani 1 1 d . . . . .
H7 H 1.025432 0.075247 0.323834 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8332(5) 0.1164(4) 0.24352(18) 0.0616(9) Uani 1 1 d . . . . .
H8A H 0.723563 0.092935 0.263142 0.074 Uiso 1 1 calc R U . . .
H8B H 0.813884 0.205773 0.214270 0.074 Uiso 1 1 calc R U . . .
C9 C 0.9252(5) -0.0368(5) 0.14239(19) 0.0696(10) Uani 1 1 d . . . . .
H9 H 0.943329 0.054552 0.117730 0.084 Uiso 1 1 calc R U . . .
C10 C 0.9108(5) -0.2906(5) 0.1722(2) 0.0715(10) Uani 1 1 d . . . . .
H10 H 0.916561 -0.405216 0.171565 0.086 Uiso 1 1 calc R U . . .
C11 C 0.8612(5) -0.1910(5) 0.22155(19) 0.0660(9) Uani 1 1 d . . . . .
H11 H 0.827114 -0.224094 0.261971 0.079 Uiso 1 1 calc R U . . .
C12 C 1.3092(4) 0.2051(4) 0.30299(17) 0.0557(8) Uani 1 1 d . . . . .
H12A H 1.315196 0.230453 0.351831 0.067 Uiso 1 1 calc R U . . .
H12B H 1.403139 0.276819 0.288003 0.067 Uiso 1 1 calc R U . . .
C13 C 1.3512(5) -0.0889(5) 0.33362(19) 0.0642(9) Uani 1 1 d . . . . .
C14 C 1.3436(4) 0.0273(4) 0.28866(17) 0.0534(8) Uani 1 1 d . . . . .
C15 C 1.3724(4) -0.0424(5) 0.22312(19) 0.0651(9) Uani 1 1 d . . . . .
H15 H 1.371271 0.018114 0.185207 0.078 Uiso 1 1 calc R U . . .
C16 C 1.4014(5) -0.2050(6) 0.2221(2) 0.0792(12) Uani 1 1 d . . . . .
H16 H 1.422359 -0.268922 0.183471 0.095 Uiso 1 1 calc R U . . .
C17 C 0.9867(4) 0.3219(4) 0.04562(15) 0.0526(8) Uani 1 1 d . . . . .
C18 C 1.1905(4) 0.3411(5) 0.05669(17) 0.0607(9) Uani 1 1 d . . . . .
H18 H 1.249707 0.336381 0.018650 0.073 Uiso 1 1 calc R U . . .
C19 C 1.2883(4) 0.3640(5) 0.11717(16) 0.0565(8) Uani 1 1 d . . . . .
H19 H 1.227994 0.374310 0.154806 0.068 Uiso 1 1 calc R U . . .
C20 C 1.4888(4) 0.3746(5) 0.12988(17) 0.0578(8) Uani 1 1 d . . . . .
N1 N 0.8688(4) -0.0323(4) 0.20277(13) 0.0555(7) Uani 1 1 d . . . . .
N2 N 0.9514(4) -0.1920(4) 0.12297(16) 0.0703(9) Uani 1 1 d . . . . .
O1 O 1.1362(3) 0.2389(3) 0.26923(10) 0.0549(6) Uani 1 1 d . . . . .
O2 O 0.9079(3) 0.2772(4) -0.01331(12) 0.0803(8) Uani 1 1 d . . . . .
O3 O 0.9081(3) 0.3499(3) 0.09599(11) 0.0639(6) Uani 1 1 d . . . . .
O4 O 1.5628(3) 0.3537(5) 0.07487(13) 0.0922(11) Uani 1 1 d . . . . .
H4 H 1.683(9) 0.359(8) 0.0863(9) 0.138 Uiso 1 1 calc R U . . .
O5 O 1.5730(3) 0.4017(4) 0.18668(13) 0.0764(8) Uani 1 1 d . . . . .
S1 S 1.39512(15) -0.28025(13) 0.29958(7) 0.0850(4) Uani 1 1 d . . . . .
Cl1 Cl 0.79893(14) 0.04206(11) 0.41437(5) 0.0757(4) Uani 1 1 d . . . . .
Cl2 Cl 0.71665(16) 0.67664(12) 0.49098(5) 0.0796(4) Uani 1 1 d . . . . .
Cl3 Cl 1.31850(15) -0.06299(15) 0.41796(5) 0.0830(4) Uani 1 1 d . . . . .
O6A O 1.5285(17) 0.202(2) -0.0652(6) 0.130(6) Uiso 0.40(2) 1 d . . P . .
O6B O 1.5449(15) 0.083(2) -0.0570(5) 0.173(5) Uiso 0.60(2) 1 d . . P . .
H2N H 1.009(7) -0.222(7) 0.079(3) 0.111(16) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C6 C1 C2 117.5(3) . . ?
C6 C1 C7 121.3(3) . . ?
C2 C1 C7 121.1(3) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 Cl1 117.5(2) . . ?
C1 C2 Cl1 120.3(2) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 Cl2 118.6(3) . . ?
C5 C4 Cl2 119.7(3) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 121.4(3) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O1 C7 C8 107.4(2) . . ?
O1 C7 C1 111.8(2) . . ?
C8 C7 C1 109.1(2) . . ?
O1 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
C1 C7 H7 109.5 . . ?
N1 C8 C7 111.3(2) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 N1 109.0(3) . . ?
N2 C9 H9 125.5 . . ?
N1 C9 H9 125.5 . . ?
C11 C10 N2 106.7(4) . . ?
C11 C10 H10 126.7 . . ?
N2 C10 H10 126.7 . . ?
C10 C11 N1 108.5(3) . . ?
C10 C11 H11 125.7 . . ?
N1 C11 H11 125.7 . . ?
O1 C12 C14 111.8(3) . . ?
O1 C12 H12A 109.2 . . ?
C14 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C14 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 S1 113.5(3) . . ?
C14 C13 Cl3 126.9(3) . . ?
S1 C13 Cl3 119.5(2) . . ?
C13 C14 C15 110.7(3) . . ?
C13 C14 C12 126.1(3) . . ?
C15 C14 C12 123.2(3) . . ?
C16 C15 C14 112.9(4) . . ?
C16 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C15 C16 S1 112.3(3) . . ?
C15 C16 H16 123.8 . . ?
S1 C16 H16 123.8 . . ?
O2 C17 O3 124.5(3) . . ?
O2 C17 C18 117.5(3) . . ?
O3 C17 C18 118.1(3) . . ?
C19 C18 C17 123.1(3) . . ?
C19 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C18 C19 C20 124.4(3) . . ?
C18 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
O5 C20 O4 124.2(3) . . ?
O5 C20 C19 121.7(3) . . ?
O4 C20 C19 114.1(3) . . ?
C9 N1 C11 107.2(3) . . ?
C9 N1 C8 126.4(3) . . ?
C11 N1 C8 126.3(3) . . ?
C9 N2 C10 108.5(3) . . ?
C9 N2 H2N 122(3) . . ?
C10 N2 H2N 130(3) . . ?
C7 O1 C12 113.1(2) . . ?
C20 O4 H4 109.5 . . ?
C16 S1 C13 90.55(19) . . ?
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
C1 C6 1.378(5) . ?
C1 C2 1.388(4) . ?
C1 C7 1.521(4) . ?
C2 C3 1.385(4) . ?
C2 Cl1 1.737(3) . ?
C3 C4 1.368(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 Cl2 1.742(3) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.426(4) . ?
C7 C8 1.511(4) . ?
C7 H7 0.9800 . ?
C8 N1 1.460(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.322(5) . ?
C9 N1 1.328(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.333(5) . ?
C10 N2 1.363(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.363(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.428(4) . ?
C12 C14 1.493(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.346(5) . ?
C13 S1 1.715(4) . ?
C13 Cl3 1.728(4) . ?
C14 C15 1.430(5) . ?
C15 C16 1.349(6) . ?
C15 H15 0.9300 . ?
C16 S1 1.706(5) . ?
C16 H16 0.9300 . ?
C17 O2 1.244(4) . ?
C17 O3 1.248(4) . ?
C17 C18 1.504(4) . ?
C18 C19 1.305(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.480(4) . ?
C19 H19 0.9300 . ?
C20 O5 1.205(4) . ?
C20 O4 1.301(4) . ?
N2 H2N 1.04(6) . ?
O4 H4 0.90(7) . ?
O6A O6B 1.006(14) . ?
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
C6 C1 C2 C3 2.1(5) . . . . ?
C7 C1 C2 C3 -175.6(3) . . . . ?
C6 C1 C2 Cl1 -177.1(2) . . . . ?
C7 C1 C2 Cl1 5.2(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
Cl1 C2 C3 C4 178.3(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C2 C3 C4 Cl2 179.7(2) . . . . ?
C3 C4 C5 C6 1.8(6) . . . . ?
Cl2 C4 C5 C6 -179.1(3) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C7 C1 C6 C5 176.3(3) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C6 C1 C7 O1 24.3(4) . . . . ?
C2 C1 C7 O1 -158.1(3) . . . . ?
C6 C1 C7 C8 -94.4(4) . . . . ?
C2 C1 C7 C8 83.2(4) . . . . ?
O1 C7 C8 N1 71.4(3) . . . . ?
C1 C7 C8 N1 -167.1(3) . . . . ?
N2 C10 C11 N1 0.7(4) . . . . ?
S1 C13 C14 C15 0.8(4) . . . . ?
Cl3 C13 C14 C15 -178.2(3) . . . . ?
S1 C13 C14 C12 -179.5(2) . . . . ?
Cl3 C13 C14 C12 1.4(5) . . . . ?
O1 C12 C14 C13 -110.5(4) . . . . ?
O1 C12 C14 C15 69.0(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C12 C14 C15 C16 179.8(3) . . . . ?
C14 C15 C16 S1 0.0(4) . . . . ?
O2 C17 C18 C19 -170.0(4) . . . . ?
O3 C17 C18 C19 9.3(6) . . . . ?
C17 C18 C19 C20 176.7(3) . . . . ?
C18 C19 C20 O5 177.4(4) . . . . ?
C18 C19 C20 O4 -2.0(6) . . . . ?
N2 C9 N1 C11 0.4(4) . . . . ?
N2 C9 N1 C8 176.7(3) . . . . ?
C10 C11 N1 C9 -0.7(4) . . . . ?
C10 C11 N1 C8 -177.0(3) . . . . ?
C7 C8 N1 C9 -100.4(4) . . . . ?
C7 C8 N1 C11 75.2(4) . . . . ?
N1 C9 N2 C10 0.0(4) . . . . ?
C11 C10 N2 C9 -0.4(4) . . . . ?
C8 C7 O1 C12 -144.8(3) . . . . ?
C1 C7 O1 C12 95.5(3) . . . . ?
C14 C12 O1 C7 73.9(3) . . . . ?
C15 C16 S1 C13 0.4(3) . . . . ?
C14 C13 S1 C16 -0.7(3) . . . . ?
Cl3 C13 S1 C16 178.4(2) . . . . ?
