# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Plakesh4182
_database_code_depnum_ccdc_archive 'CCDC 1575062'
_audit_update_record             
;
2017-09-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F3 N O4 S'
_chemical_formula_moiety         'C16 H12 F3 N O4 S'
_chemical_formula_weight         371.33
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.4561(3)
_cell_length_b                   8.5762(3)
_cell_length_c                   12.4229(4)
_cell_angle_alpha                110.0467(9)
_cell_angle_beta                 111.9415(10)
_cell_angle_gamma                90.1156(11)
_cell_volume                     776.24(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6971
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380.00
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_T_max  0.974

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7612
_diffrn_reflns_av_R_equivalents  0.0101
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3523
_reflns_number_gt                3168
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1547
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3523
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1142P)²+0.1372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15675(5) 0.36702(5) 0.17167(4) 0.02265(17) Uani 1.0 2 d . . .
F1 F 0.88269(16) 0.44236(16) 0.37504(12) 0.0437(4) Uani 1.0 2 d . . .
F2 F 0.63606(15) 0.34137(16) 0.35683(10) 0.0370(3) Uani 1.0 2 d . . .
F3 F 0.80574(16) 0.17531(15) 0.30264(11) 0.0380(3) Uani 1.0 2 d . . .
O1 O 0.53449(14) 0.18372(13) 0.09554(10) 0.0206(3) Uani 1.0 2 d . . .
O2 O 0.26794(15) 0.07069(14) 0.03787(11) 0.0247(3) Uani 1.0 2 d . . .
O3 O 0.17522(18) 0.53854(16) 0.25067(14) 0.0335(4) Uani 1.0 2 d . . .
O4 O 0.00617(15) 0.29697(18) 0.05860(13) 0.0331(4) Uani 1.0 2 d . . .
N1 N 0.33323(17) 0.35666(16) 0.13491(13) 0.0196(3) Uani 1.0 2 d . . .
C1 C 0.3716(2) 0.19577(19) 0.08584(14) 0.0185(3) Uani 1.0 2 d . . .
C2 C 0.67019(19) 0.32358(19) 0.17170(15) 0.0197(4) Uani 1.0 2 d . . .
C3 C 0.7494(2) 0.3206(2) 0.30306(16) 0.0249(4) Uani 1.0 2 d . . .
C4 C 0.6094(2) 0.48783(19) 0.17100(14) 0.0194(4) Uani 1.0 2 d . . .
C5 C 0.7183(3) 0.6206(2) 0.18297(16) 0.0258(4) Uani 1.0 2 d . . .
C6 C 0.6559(3) 0.7682(2) 0.17809(17) 0.0295(4) Uani 1.0 2 d . . .
C7 C 0.4845(3) 0.7809(2) 0.15713(16) 0.0286(4) Uani 1.0 2 d . . .
C8 C 0.3730(3) 0.6475(2) 0.14178(16) 0.0247(4) Uani 1.0 2 d . . .
C9 C 0.4385(2) 0.50232(19) 0.15234(14) 0.0185(3) Uani 1.0 2 d . . .
C10 C 0.1865(2) 0.2405(2) 0.26066(15) 0.0217(4) Uani 1.0 2 d . . .
C11 C 0.2838(3) 0.3138(3) 0.38890(17) 0.0300(4) Uani 1.0 2 d . . .
C12 C 0.3042(3) 0.2166(3) 0.46076(18) 0.0376(5) Uani 1.0 2 d . . .
C13 C 0.2285(3) 0.0483(3) 0.40690(18) 0.0334(5) Uani 1.0 2 d . . .
C14 C 0.1317(3) -0.0201(3) 0.27922(17) 0.0283(4) Uani 1.0 2 d . . .
C15 C 0.1075(3) 0.0737(3) 0.20417(16) 0.0249(4) Uani 1.0 2 d . . .
C16 C 0.2508(4) -0.0559(4) 0.4860(3) 0.0538(7) Uani 1.0 2 d . . .
H2 H 0.7611 0.3074 0.1371 0.0237 Uiso 1.0 2 calc R . .
H5 H 0.8347 0.6099 0.1944 0.0310 Uiso 1.0 2 calc R . .
H6 H 0.7304 0.8606 0.1891 0.0354 Uiso 1.0 2 calc R . .
H7 H 0.4422 0.8821 0.1531 0.0343 Uiso 1.0 2 calc R . .
H8 H 0.2547 0.6557 0.1244 0.0296 Uiso 1.0 2 calc R . .
H11 H 0.3351 0.4282 0.4263 0.0360 Uiso 1.0 2 calc R . .
H12 H 0.3708 0.2651 0.5482 0.0451 Uiso 1.0 2 calc R . .
H14 H 0.0804 -0.1345 0.2419 0.0340 Uiso 1.0 2 calc R . .
H15 H 0.0391 0.0256 0.1170 0.0298 Uiso 1.0 2 calc R . .
H16A H 0.3226 0.0127 0.5733 0.0646 Uiso 1.0 2 calc R . .
H16B H 0.1377 -0.0961 0.4793 0.0646 Uiso 1.0 2 calc R . .
H16C H 0.3068 -0.1521 0.4569 0.0646 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O3 1.4304(13) yes . .
S1 O4 1.4273(12) yes . .
S1 N1 1.7104(18) yes . .
S1 C10 1.754(3) yes . .
F1 C3 1.3275(19) yes . .
F2 C3 1.339(3) yes . .
F3 C3 1.334(3) yes . .
O1 C1 1.344(3) yes . .
O1 C2 1.4338(17) yes . .
O2 C1 1.2009(19) yes . .
N1 C1 1.398(2) yes . .
N1 C9 1.437(3) yes . .
C2 C3 1.524(3) yes . .
C2 C4 1.502(3) yes . .
C4 C5 1.395(3) yes . .
C4 C9 1.388(3) yes . .
C5 C6 1.384(3) yes . .
C6 C7 1.384(3) yes . .
C7 C8 1.394(3) yes . .
C8 C9 1.391(3) yes . .
C10 C11 1.393(3) yes . .
C10 C15 1.394(3) yes . .
C11 C12 1.385(4) yes . .
C12 C13 1.398(3) yes . .
C13 C14 1.386(3) yes . .
C13 C16 1.504(5) yes . .
C14 C15 1.390(4) yes . .
C2 H2 1.000 no . .
C5 H5 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C16 H16A 0.980 no . .
C16 H16B 0.980 no . .
C16 H16C 0.980 no . .

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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O3 S1 O4 119.26(9) yes . . .
O3 S1 N1 104.45(9) yes . . .
O3 S1 C10 109.11(10) yes . . .
O4 S1 N1 108.50(9) yes . . .
O4 S1 C10 110.11(9) yes . . .
N1 S1 C10 104.26(9) yes . . .
C1 O1 C2 121.70(12) yes . . .
S1 N1 C1 116.07(13) yes . . .
S1 N1 C9 123.27(12) yes . . .
C1 N1 C9 120.66(16) yes . . .
O1 C1 O2 119.56(15) yes . . .
O1 C1 N1 117.06(13) yes . . .
O2 C1 N1 123.37(17) yes . . .
O1 C2 C3 108.16(16) yes . . .
O1 C2 C4 112.43(12) yes . . .
C3 C2 C4 112.30(13) yes . . .
F1 C3 F2 108.02(14) yes . . .
F1 C3 F3 107.76(14) yes . . .
F1 C3 C2 110.20(18) yes . . .
F2 C3 F3 106.91(19) yes . . .
F2 C3 C2 112.05(14) yes . . .
F3 C3 C2 111.70(14) yes . . .
C2 C4 C5 121.39(16) yes . . .
C2 C4 C9 118.25(16) yes . . .
C5 C4 C9 120.29(16) yes . . .
C4 C5 C6 119.62(18) yes . . .
C5 C6 C7 119.82(19) yes . . .
C6 C7 C8 121.15(18) yes . . .
C7 C8 C9 118.70(17) yes . . .
N1 C9 C4 116.62(15) yes . . .
N1 C9 C8 122.88(16) yes . . .
C4 C9 C8 120.31(17) yes . . .
S1 C10 C11 118.14(14) yes . . .
S1 C10 C15 120.20(13) yes . . .
C11 C10 C15 121.6(2) yes . . .
C10 C11 C12 118.73(17) yes . . .
C11 C12 C13 121.17(17) yes . . .
C12 C13 C14 118.5(3) yes . . .
C12 C13 C16 120.71(18) yes . . .
C14 C13 C16 120.77(19) yes . . .
C13 C14 C15 121.97(17) yes . . .
C10 C15 C14 118.00(15) yes . . .
O1 C2 H2 107.925 no . . .
C3 C2 H2 107.921 no . . .
C4 C2 H2 107.930 no . . .
C4 C5 H5 120.193 no . . .
C6 C5 H5 120.189 no . . .
C5 C6 H6 120.086 no . . .
C7 C6 H6 120.091 no . . .
C6 C7 H7 119.424 no . . .
C8 C7 H7 119.427 no . . .
C7 C8 H8 120.647 no . . .
C9 C8 H8 120.650 no . . .
C10 C11 H11 120.635 no . . .
C12 C11 H11 120.632 no . . .
C11 C12 H12 119.420 no . . .
C13 C12 H12 119.414 no . . .
C13 C14 H14 119.017 no . . .
C15 C14 H14 119.013 no . . .
C10 C15 H15 121.001 no . . .
C14 C15 H15 120.997 no . . .
C13 C16 H16A 109.475 no . . .
C13 C16 H16B 109.477 no . . .
C13 C16 H16C 109.476 no . . .
H16A C16 H16B 109.462 no . . .
H16A C16 H16C 109.470 no . . .
H16B C16 H16C 109.467 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 S1 N1 C1 163.81(11) no . . . .
O3 S1 N1 C9 -16.16(14) no . . . .
O3 S1 C10 C11 -24.45(16) no . . . .
O3 S1 C10 C15 152.60(13) no . . . .
O4 S1 N1 C1 -67.98(13) no . . . .
O4 S1 N1 C9 112.05(12) no . . . .
O4 S1 C10 C11 -157.10(12) no . . . .
O4 S1 C10 C15 19.94(17) no . . . .
N1 S1 C10 C11 86.69(13) no . . . .
N1 S1 C10 C15 -96.27(13) no . . . .
C10 S1 N1 C1 49.34(11) no . . . .
C10 S1 N1 C9 -130.63(11) no . . . .
C1 O1 C2 C3 89.15(17) no . . . .
C1 O1 C2 C4 -35.4(3) no . . . .
C2 O1 C1 O2 -168.19(15) no . . . .
C2 O1 C1 N1 10.9(3) no . . . .
S1 N1 C1 O1 -158.03(12) no . . . .
S1 N1 C1 O2 21.1(3) no . . . .
S1 N1 C9 C4 153.14(11) no . . . .
S1 N1 C9 C8 -31.8(2) no . . . .
C1 N1 C9 C4 -26.8(2) no . . . .
C1 N1 C9 C8 148.22(14) no . . . .
C9 N1 C1 O1 21.9(3) no . . . .
C9 N1 C1 O2 -158.97(16) no . . . .
O1 C2 C3 F1 176.27(13) no . . . .
O1 C2 C3 F2 -63.41(16) no . . . .
O1 C2 C3 F3 56.52(18) no . . . .
O1 C2 C4 C5 -148.25(14) no . . . .
O1 C2 C4 C9 28.9(3) no . . . .
C3 C2 C4 C5 89.5(2) no . . . .
C3 C2 C4 C9 -93.39(16) no . . . .
C4 C2 C3 F1 -59.08(19) no . . . .
C4 C2 C3 F2 61.23(18) no . . . .
C4 C2 C3 F3 -178.83(14) no . . . .
C2 C4 C5 C6 178.05(14) no . . . .
C2 C4 C9 N1 -0.1(3) no . . . .
C2 C4 C9 C8 -175.27(13) no . . . .
C5 C4 C9 N1 177.06(14) no . . . .
C5 C4 C9 C8 1.9(3) no . . . .
C9 C4 C5 C6 1.0(3) no . . . .
C4 C5 C6 C7 -2.2(3) no . . . .
C5 C6 C7 C8 0.6(3) no . . . .
C6 C7 C8 C9 2.3(3) no . . . .
C7 C8 C9 N1 -178.35(15) no . . . .
C7 C8 C9 C4 -3.5(3) no . . . .
S1 C10 C11 C12 178.18(13) no . . . .
S1 C10 C15 C14 -178.48(12) no . . . .
C11 C10 C15 C14 -1.5(3) no . . . .
C15 C10 C11 C12 1.2(3) no . . . .
C10 C11 C12 C13 -0.4(4) no . . . .
C11 C12 C13 C14 -0.0(4) no . . . .
C11 C12 C13 C16 -179.7(2) no . . . .
C12 C13 C14 C15 -0.4(4) no . . . .
C16 C13 C14 C15 179.3(3) no . . . .
C13 C14 C15 C10 1.1(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O2 2.8961(13) no . .
S1 C8 3.221(3) no . .
F1 O1 3.5636(14) no . .
F1 C4 2.867(2) no . .
F1 C5 3.161(3) no . .
F2 O1 2.8293(16) no . .
F2 N1 3.0246(18) no . .
F2 C1 3.0616(17) no . .
F2 C4 2.925(3) no . .
F2 C9 3.224(3) no . .
F2 C10 3.537(2) no . .
F2 C11 3.168(3) no . .
F3 O1 2.7574(16) no . .
O1 C9 2.782(2) no . .
O2 O4 2.9720(19) no . .
O2 C2 3.5086(19) no . .
O2 C9 3.556(2) no . .
O2 C10 2.987(3) no . .
O2 C15 2.858(3) no . .
O3 C8 2.838(3) no . .
O3 C9 2.885(3) no . .
O3 C11 2.934(3) no . .
O4 C1 3.138(3) no . .
O4 C15 2.982(3) no . .
N1 C2 2.744(3) no . .
N1 C3 3.435(2) no . .
N1 C11 3.471(3) no . .
N1 C15 3.593(3) no . .
C1 C3 3.193(2) no . .
C1 C4 2.830(3) no . .
C1 C10 3.047(3) no . .
C1 C15 3.427(3) no . .
C3 C5 3.355(3) no . .
C3 C9 3.344(3) no . .
C4 C7 2.763(3) no . .
C5 C8 2.794(3) no . .
C6 C9 2.779(3) no . .
C10 C13 2.778(4) no . .
C11 C14 2.776(3) no . .
C12 C15 2.789(3) no . .
F1 F1 2.7995(17) no . 2_766
F1 O3 3.593(3) no . 1_655
F1 C10 3.560(3) no . 1_655
F1 C11 3.530(3) no . 1_655
F2 C11 3.342(2) no . 2_666
F2 C16 3.552(4) no . 2_656
F3 C6 3.317(2) no . 1_545
F3 C10 3.521(3) no . 1_655
F3 C14 3.283(3) no . 1_655
F3 C15 3.222(3) no . 1_655
F3 C16 3.310(4) no . 2_656
O1 O1 3.1201(14) no . 2_655
O1 O2 3.1470(18) no . 2_655
O1 C1 3.5523(19) no . 2_655
O1 C6 3.345(3) no . 2_665
O1 C7 3.201(3) no . 2_665
O2 O1 3.1470(18) no . 2_655
O2 O4 3.4720(19) no . 2_555
O2 C7 3.499(3) no . 1_545
O2 C15 3.3094(18) no . 2_555
O3 F1 3.593(3) no . 1_455
O3 C16 3.560(3) no . 1_565
O4 O2 3.4720(19) no . 2_555
O4 C2 3.587(3) no . 1_455
O4 C8 3.400(2) no . 2_565
O4 C15 3.495(2) no . 2_555
C1 O1 3.5523(19) no . 2_655
C1 C6 3.320(3) no . 2_665
C2 O4 3.587(3) no . 1_655
C2 C7 3.563(3) no . 2_665
C6 F3 3.317(2) no . 1_565
C6 O1 3.345(3) no . 2_665
C6 C1 3.320(3) no . 2_665
C7 O1 3.201(3) no . 2_665
C7 O2 3.499(3) no . 1_565
C7 C2 3.563(3) no . 2_665
C8 O4 3.400(2) no . 2_565
C10 F1 3.560(3) no . 1_455
C10 F3 3.521(3) no . 1_455
C11 F1 3.530(3) no . 1_455
C11 F2 3.342(2) no . 2_666
C14 F3 3.283(3) no . 1_455
C15 F3 3.222(3) no . 1_455
C15 O2 3.3094(18) no . 2_555
C15 O4 3.495(2) no . 2_555
C16 F2 3.552(4) no . 2_656
C16 F3 3.310(4) no . 2_656
C16 O3 3.560(3) no . 1_545
S1 H8 2.9173 no . .
S1 H11 2.8018 no . .
S1 H15 2.8533 no . .
F1 H2 2.5514 no . .
F1 H5 2.9657 no . .
F2 H2 3.2033 no . .
F2 H11 2.9974 no . .
F3 H2 2.5825 no . .
O2 H15 2.5565 no . .
O3 H8 2.4053 no . .
O3 H11 2.5885 no . .
O4 H8 3.3934 no . .
O4 H15 2.6507 no . .
N1 H8 2.6846 no . .
N1 H11 3.4519 no . .
C1 H2 3.1884 no . .
C1 H15 3.3713 no . .
C2 H5 2.6948 no . .
C3 H5 3.3931 no . .
C4 H6 3.2617 no . .
C4 H8 3.2706 no . .
C5 H2 2.6040 no . .
C5 H7 3.2504 no . .
C6 H8 3.2771 no . .
C7 H5 3.2549 no . .
C8 H6 3.2753 no . .
C9 H2 3.2335 no . .
C9 H5 3.2708 no . .
C9 H7 3.2539 no . .
C10 H12 3.2489 no . .
C10 H14 3.2436 no . .
C11 H15 3.2911 no . .
C12 H14 3.2496 no . .
C12 H16A 2.5603 no . .
C12 H16B 3.1426 no . .
C12 H16C 3.1460 no . .
C13 H11 3.2824 no . .
C13 H15 3.2838 no . .
C14 H12 3.2502 no . .
C14 H16A 3.3048 no . .
C14 H16B 2.7608 no . .
C14 H16C 2.7608 no . .
C15 H11 3.2889 no . .
C16 H12 2.6738 no . .
C16 H14 2.6564 no . .
H2 H5 2.4539 no . .
H5 H6 2.3386 no . .
H6 H7 2.3275 no . .
H7 H8 2.3455 no . .
H11 H12 2.3352 no . .
H12 H16A 2.3466 no . .
H12 H16B 3.3332 no . .
H12 H16C 3.3367 no . .
H14 H15 2.3397 no . .
H14 H16A 3.5872 no . .
H14 H16B 2.7033 no . .
H14 H16C 2.6975 no . .
S1 H2 3.2268 no . 1_455
S1 H5 3.4678 no . 1_455
F1 H11 3.4987 no . 2_666
F1 H12 3.4216 no . 2_666
F2 H11 2.6608 no . 2_666
F2 H12 3.1792 no . 2_666
F2 H16A 3.4171 no . 2_656
F2 H16B 3.5032 no . 2_656
F2 H16C 3.1571 no . 2_656
F3 H6 2.5283 no . 1_545
F3 H7 3.4240 no . 1_545
F3 H15 3.4994 no . 1_655
F3 H16A 3.0156 no . 2_656
F3 H16B 2.8853 no . 2_656
F3 H16C 3.5216 no . 2_656
O1 H6 3.5443 no . 1_545
O1 H6 3.2895 no . 2_665
O1 H7 3.0806 no . 1_545
O1 H7 3.0269 no . 2_665
O2 H2 3.1726 no . 2_655
O2 H6 3.0769 no . 2_665
O2 H7 2.6186 no . 1_545
O2 H15 2.5090 no . 2_555
O3 H2 3.5425 no . 1_455
O3 H5 2.8192 no . 1_455
O3 H14 2.9445 no . 1_565
O3 H16B 3.5443 no . 1_565
O3 H16C 2.8350 no . 1_565
O4 H2 2.5902 no . 1_455
O4 H5 3.2997 no . 1_455
O4 H8 2.6625 no . 2_565
O4 H14 3.2859 no . 2_555
O4 H15 2.7917 no . 2_555
C1 H6 3.0510 no . 2_665
C1 H7 3.0767 no . 1_545
C1 H15 3.4890 no . 2_555
C2 H7 3.5422 no . 2_665
C4 H12 3.3437 no . 2_666
C5 H12 3.5102 no . 2_666
C5 H14 3.4010 no . 1_665
C6 H12 3.5962 no . 2_666
C6 H14 3.4092 no . 1_665
C6 H16A 2.9495 no . 2_666
C7 H2 3.2670 no . 2_665
C7 H12 3.5631 no . 2_666
C7 H16A 2.9749 no . 2_666
C8 H2 3.3803 no . 2_665
C8 H12 3.4447 no . 2_666
C8 H14 3.4477 no . 1_565
C9 H12 3.2916 no . 2_666
C10 H2 3.4805 no . 1_455
C11 H11 3.3930 no . 2_666
C12 H16C 3.1712 no . 2_656
C14 H6 3.1908 no . 1_445
C14 H7 3.4970 no . 1_545
C14 H8 3.2172 no . 1_545
C15 H2 3.5547 no . 1_455
C15 H6 3.5839 no . 1_445
C15 H7 3.4287 no . 1_545
C15 H15 3.4853 no . 2_555
H2 S1 3.2268 no . 1_655
H2 O2 3.1726 no . 2_655
H2 O3 3.5425 no . 1_655
H2 O4 2.5902 no . 1_655
H2 C7 3.2670 no . 2_665
H2 C8 3.3803 no . 2_665
H2 C10 3.4805 no . 1_655
H2 C15 3.5547 no . 1_655
H2 H7 3.1526 no . 2_665
H2 H8 3.3258 no . 2_665
H2 H15 3.3880 no . 1_655
H5 S1 3.4678 no . 1_655
H5 O3 2.8192 no . 1_655
H5 O4 3.2997 no . 1_655
H5 H14 2.7659 no . 1_665
H5 H16B 3.5392 no . 1_665
H6 F3 2.5283 no . 1_565
H6 O1 3.5443 no . 1_565
H6 O1 3.2895 no . 2_665
H6 O2 3.0769 no . 2_665
H6 C1 3.0510 no . 2_665
H6 C14 3.1908 no . 1_665
H6 C15 3.5839 no . 1_665
H6 H14 2.7794 no . 1_665
H6 H15 3.4969 no . 1_665
H6 H16A 2.9801 no . 2_666
H7 F3 3.4240 no . 1_565
H7 O1 3.0806 no . 1_565
H7 O1 3.0269 no . 2_665
H7 O2 2.6186 no . 1_565
H7 C1 3.0767 no . 1_565
H7 C2 3.5422 no . 2_665
H7 C14 3.4970 no . 1_565
H7 C15 3.4287 no . 1_565
H7 H2 3.1526 no . 2_665
H7 H15 3.5473 no . 1_565
H7 H16A 3.0260 no . 2_666
H8 O4 2.6625 no . 2_565
H8 C14 3.2172 no . 1_565
H8 H2 3.3258 no . 2_665
H8 H14 2.7118 no . 1_565
H11 F1 3.4987 no . 2_666
H11 F2 2.6608 no . 2_666
H11 C11 3.3930 no . 2_666
H11 H11 2.6963 no . 2_666
H11 H12 3.4665 no . 2_666
H11 H16C 3.5059 no . 1_565
H12 F1 3.4216 no . 2_666
H12 F2 3.1792 no . 2_666
H12 C4 3.3437 no . 2_666
H12 C5 3.5102 no . 2_666
H12 C6 3.5962 no . 2_666
H12 C7 3.5631 no . 2_666
H12 C8 3.4447 no . 2_666
H12 C9 3.2916 no . 2_666
H12 H11 3.4665 no . 2_666
H12 H16C 2.9112 no . 2_656
H14 O3 2.9445 no . 1_545
H14 O4 3.2859 no . 2_555
H14 C5 3.4010 no . 1_445
H14 C6 3.4092 no . 1_445
H14 C8 3.4477 no . 1_545
H14 H5 2.7659 no . 1_445
H14 H6 2.7794 no . 1_445
H14 H8 2.7118 no . 1_545
H15 F3 3.4994 no . 1_455
H15 O2 2.5090 no . 2_555
H15 O4 2.7917 no . 2_555
H15 C1 3.4890 no . 2_555
H15 C15 3.4853 no . 2_555
H15 H2 3.3880 no . 1_455
H15 H6 3.4969 no . 1_445
H15 H7 3.5473 no . 1_545
H15 H15 2.6004 no . 2_555
H16A F2 3.4171 no . 2_656
H16A F3 3.0156 no . 2_656
H16A C6 2.9495 no . 2_666
H16A C7 2.9749 no . 2_666
H16A H6 2.9801 no . 2_666
H16A H7 3.0260 no . 2_666
H16A H16C 3.5452 no . 2_656
H16B F2 3.5032 no . 2_656
H16B F3 2.8853 no . 2_656
H16B O3 3.5443 no . 1_545
H16B H5 3.5392 no . 1_445
H16B H16B 2.9552 no . 2_556
H16C F2 3.1571 no . 2_656
H16C F3 3.5216 no . 2_656
H16C O3 2.8350 no . 1_545
H16C C12 3.1712 no . 2_656
H16C H11 3.5059 no . 1_545
H16C H12 2.9112 no . 2_656
H16C H16A 3.5452 no . 2_656

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_170512plakesh1
_database_code_depnum_ccdc_archive 'CCDC 1575063'
_audit_update_record             
;
2017-09-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H22 F3 N O3 S'
_chemical_formula_moiety         'C25 H22 F3 N O3 S'
_chemical_formula_weight         473.51
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   16.8152(3)
_cell_length_b                   15.0512(3)
_cell_length_c                   17.5637(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     4445.18(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    34842
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.43
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968.00
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.961

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            40949
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             5057
_reflns_number_gt                4162
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1214
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5057
_refine_ls_number_parameters     298
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0607P)²+1.7845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.97395(2) 0.35773(3) 0.62935(2) 0.02474(12) Uani 1.0 8 d . . .
F1 F 1.00103(9) 0.23075(9) 0.86068(9) 0.0601(4) Uani 1.0 8 d . . .
F2 F 0.98394(8) 0.30171(10) 0.96563(8) 0.0557(4) Uani 1.0 8 d . . .
F3 F 1.09486(8) 0.31215(10) 0.90626(8) 0.0560(4) Uani 1.0 8 d . . .
O1 O 0.99959(7) 0.46062(8) 0.89755(7) 0.0299(3) Uani 1.0 8 d . . .
O2 O 0.97540(7) 0.27108(9) 0.66281(7) 0.0334(3) Uani 1.0 8 d . . .
O3 O 1.04478(7) 0.39591(9) 0.59749(7) 0.0334(3) Uani 1.0 8 d . . .
N1 N 0.94520(8) 0.42726(10) 0.69590(8) 0.0246(3) Uani 1.0 8 d . . .
C1 C 0.88236(9) 0.40262(11) 0.74789(10) 0.0249(4) Uani 1.0 8 d . . .
C2 C 0.80311(10) 0.40835(12) 0.72465(11) 0.0306(4) Uani 1.0 8 d . . .
C3 C 0.74258(11) 0.38713(13) 0.77538(12) 0.0351(5) Uani 1.0 8 d . . .
C4 C 0.76093(11) 0.36196(13) 0.84908(12) 0.0367(5) Uani 1.0 8 d . . .
C5 C 0.83953(11) 0.35918(13) 0.87314(11) 0.0330(4) Uani 1.0 8 d . . .
C6 C 0.90137(10) 0.37940(11) 0.82277(10) 0.0253(4) Uani 1.0 8 d . . .
C7 C 0.98687(10) 0.38574(12) 0.84962(10) 0.0266(4) Uani 1.0 8 d . . .
C8 C 1.01569(12) 0.30710(14) 0.89609(12) 0.0387(5) Uani 1.0 8 d . . .
C9 C 0.99519(10) 0.54498(12) 0.85878(10) 0.0276(4) Uani 1.0 8 d . . .
C10 C 1.05935(9) 0.55675(11) 0.79934(9) 0.0233(4) Uani 1.0 8 d . . .
C11 C 1.04528(10) 0.54485(11) 0.72516(10) 0.0254(4) Uani 1.0 8 d . . .
C12 C 0.96631(10) 0.52296(12) 0.68897(10) 0.0268(4) Uani 1.0 8 d . . .
C13 C 1.14024(9) 0.58070(11) 0.82736(10) 0.0249(4) Uani 1.0 8 d . . .
C14 C 1.16532(11) 0.55493(12) 0.90002(11) 0.0308(4) Uani 1.0 8 d . . .
C15 C 1.24081(11) 0.57757(13) 0.92609(12) 0.0364(5) Uani 1.0 8 d . . .
C16 C 1.29201(11) 0.62606(13) 0.88070(12) 0.0365(5) Uani 1.0 8 d . . .
C17 C 1.26756(11) 0.65314(13) 0.80915(12) 0.0367(5) Uani 1.0 8 d . . .
C18 C 1.19203(11) 0.63132(12) 0.78260(11) 0.0308(4) Uani 1.0 8 d . . .
C19 C 0.89910(9) 0.35934(11) 0.55876(9) 0.0236(4) Uani 1.0 8 d . . .
C20 C 0.89896(10) 0.42557(12) 0.50360(9) 0.0271(4) Uani 1.0 8 d . . .
C21 C 0.83565(10) 0.43171(12) 0.45342(9) 0.0287(4) Uani 1.0 8 d . . .
C22 C 0.77187(10) 0.37299(12) 0.45772(9) 0.0280(4) Uani 1.0 8 d . . .
C23 C 0.77400(10) 0.30570(12) 0.51217(10) 0.0294(4) Uani 1.0 8 d . . .
C24 C 0.83717(10) 0.29826(11) 0.56266(10) 0.0275(4) Uani 1.0 8 d . . .
C25 C 0.70020(12) 0.38393(16) 0.40712(12) 0.0418(5) Uani 1.0 8 d . . .
H2 H 0.7906 0.4267 0.6743 0.0367 Uiso 1.0 8 calc R . .
H3 H 0.6886 0.3899 0.7595 0.0422 Uiso 1.0 8 calc R . .
H4 H 0.7195 0.3465 0.8834 0.0440 Uiso 1.0 8 calc R . .
H5 H 0.8514 0.3434 0.9243 0.0396 Uiso 1.0 8 calc R . .
H7 H 1.0219 0.3918 0.8039 0.0319 Uiso 1.0 8 calc R . .
H9A H 0.9997 0.5933 0.8968 0.0331 Uiso 1.0 8 calc R . .
H9B H 0.9425 0.5503 0.8340 0.0331 Uiso 1.0 8 calc R . .
H11 H 1.0895 0.5508 0.6918 0.0304 Uiso 1.0 8 calc R . .
H12A H 0.9243 0.5591 0.7134 0.0322 Uiso 1.0 8 calc R . .
H12B H 0.9682 0.5392 0.6344 0.0322 Uiso 1.0 8 calc R . .
H14 H 1.1306 0.5217 0.9318 0.0369 Uiso 1.0 8 calc R . .
H15 H 1.2573 0.5595 0.9755 0.0437 Uiso 1.0 8 calc R . .
H16 H 1.3437 0.6407 0.8985 0.0438 Uiso 1.0 8 calc R . .
H17 H 1.3025 0.6868 0.7780 0.0441 Uiso 1.0 8 calc R . .
H18 H 1.1755 0.6510 0.7337 0.0370 Uiso 1.0 8 calc R . .
H20 H 0.9420 0.4663 0.5003 0.0325 Uiso 1.0 8 calc R . .
H21 H 0.8358 0.4767 0.4155 0.0345 Uiso 1.0 8 calc R . .
H23 H 0.7315 0.2642 0.5148 0.0353 Uiso 1.0 8 calc R . .
H24 H 0.8381 0.2520 0.5994 0.0330 Uiso 1.0 8 calc R . .
H25A H 0.6617 0.3368 0.4181 0.0502 Uiso 1.0 8 calc R . .
H25B H 0.6757 0.4420 0.4166 0.0502 Uiso 1.0 8 calc R . .
H25C H 0.7166 0.3802 0.3537 0.0502 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O2 1.4307(14) yes . .
S1 O3 1.4359(13) yes . .
S1 N1 1.6417(15) yes . .
S1 C19 1.7669(16) yes . .
F1 C8 1.330(3) yes . .
F2 C8 1.335(3) yes . .
F3 C8 1.345(3) yes . .
O1 C7 1.423(3) yes . .
O1 C9 1.443(3) yes . .
N1 C1 1.445(3) yes . .
N1 C12 1.488(3) yes . .
C1 C2 1.396(3) yes . .
C1 C6 1.398(3) yes . .
C2 C3 1.390(3) yes . .
C3 C4 1.384(3) yes . .
C4 C5 1.388(3) yes . .
C5 C6 1.399(3) yes . .
C6 C7 1.516(3) yes . .
C7 C8 1.517(3) yes . .
C9 C10 1.512(3) yes . .
C10 C11 1.336(3) yes . .
C10 C13 1.491(3) yes . .
C11 C12 1.509(3) yes . .
C13 C14 1.399(3) yes . .
C13 C18 1.399(3) yes . .
C14 C15 1.392(3) yes . .
C15 C16 1.382(3) yes . .
C16 C17 1.384(3) yes . .
C17 C18 1.392(3) yes . .
C19 C20 1.390(3) yes . .
C19 C24 1.391(3) yes . .
C20 C21 1.385(3) yes . .
C21 C22 1.392(3) yes . .
C22 C23 1.393(3) yes . .
C22 C25 1.506(3) yes . .
C23 C24 1.388(3) yes . .
C2 H2 0.950 no . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C7 H7 1.000 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C11 H11 0.950 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C16 H16 0.950 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .
C23 H23 0.950 no . .
C24 H24 0.950 no . .
C25 H25A 0.980 no . .
C25 H25B 0.980 no . .
C25 H25C 0.980 no . .

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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O2 S1 O3 120.71(8) yes . . .
O2 S1 N1 107.08(8) yes . . .
O2 S1 C19 108.23(8) yes . . .
O3 S1 N1 105.46(8) yes . . .
O3 S1 C19 108.17(8) yes . . .
N1 S1 C19 106.33(8) yes . . .
C7 O1 C9 114.21(13) yes . . .
S1 N1 C1 120.11(12) yes . . .
S1 N1 C12 119.24(12) yes . . .
C1 N1 C12 118.32(14) yes . . .
N1 C1 C2 119.82(16) yes . . .
N1 C1 C6 119.44(14) yes . . .
C2 C1 C6 120.58(16) yes . . .
C1 C2 C3 119.82(18) yes . . .
C2 C3 C4 119.96(18) yes . . .
C3 C4 C5 120.36(18) yes . . .
C4 C5 C6 120.58(18) yes . . .
C1 C6 C5 118.65(16) yes . . .
C1 C6 C7 119.59(15) yes . . .
C5 C6 C7 121.46(16) yes . . .
O1 C7 C6 112.11(14) yes . . .
O1 C7 C8 104.57(15) yes . . .
C6 C7 C8 114.91(15) yes . . .
F1 C8 F2 107.53(18) yes . . .
F1 C8 F3 107.12(17) yes . . .
F1 C8 C7 111.31(17) yes . . .
F2 C8 F3 106.12(17) yes . . .
F2 C8 C7 114.31(17) yes . . .
F3 C8 C7 110.08(17) yes . . .
O1 C9 C10 113.11(14) yes . . .
C9 C10 C11 122.09(15) yes . . .
C9 C10 C13 116.84(14) yes . . .
C11 C10 C13 121.05(15) yes . . .
C10 C11 C12 126.58(16) yes . . .
N1 C12 C11 112.76(14) yes . . .
C10 C13 C14 120.61(15) yes . . .
C10 C13 C18 120.94(16) yes . . .
C14 C13 C18 118.43(16) yes . . .
C13 C14 C15 120.48(17) yes . . .
C14 C15 C16 120.51(19) yes . . .
C15 C16 C17 119.63(18) yes . . .
C16 C17 C18 120.38(18) yes . . .
C13 C18 C17 120.54(18) yes . . .
S1 C19 C20 120.01(13) yes . . .
S1 C19 C24 119.32(13) yes . . .
C20 C19 C24 120.47(15) yes . . .
C19 C20 C21 119.51(16) yes . . .
C20 C21 C22 121.02(16) yes . . .
C21 C22 C23 118.62(16) yes . . .
C21 C22 C25 121.00(17) yes . . .
C23 C22 C25 120.33(17) yes . . .
C22 C23 C24 121.11(16) yes . . .
C19 C24 C23 119.22(16) yes . . .
C1 C2 H2 120.090 no . . .
C3 C2 H2 120.091 no . . .
C2 C3 H3 120.018 no . . .
C4 C3 H3 120.024 no . . .
C3 C4 H4 119.819 no . . .
C5 C4 H4 119.825 no . . .
C4 C5 H5 119.720 no . . .
C6 C5 H5 119.704 no . . .
O1 C7 H7 108.336 no . . .
C6 C7 H7 108.337 no . . .
C8 C7 H7 108.336 no . . .
O1 C9 H9A 108.959 no . . .
O1 C9 H9B 108.948 no . . .
C10 C9 H9A 108.961 no . . .
C10 C9 H9B 108.964 no . . .
H9A C9 H9B 107.762 no . . .
C10 C11 H11 116.701 no . . .
C12 C11 H11 116.719 no . . .
N1 C12 H12A 109.040 no . . .
N1 C12 H12B 109.041 no . . .
C11 C12 H12A 109.030 no . . .
C11 C12 H12B 109.035 no . . .
H12A C12 H12B 107.819 no . . .
C13 C14 H14 119.767 no . . .
C15 C14 H14 119.756 no . . .
C14 C15 H15 119.748 no . . .
C16 C15 H15 119.738 no . . .
C15 C16 H16 120.184 no . . .
C17 C16 H16 120.182 no . . .
C16 C17 H17 119.810 no . . .
C18 C17 H17 119.807 no . . .
C13 C18 H18 119.732 no . . .
C17 C18 H18 119.728 no . . .
C19 C20 H20 120.245 no . . .
C21 C20 H20 120.243 no . . .
C20 C21 H21 119.489 no . . .
C22 C21 H21 119.490 no . . .
C22 C23 H23 119.442 no . . .
C24 C23 H23 119.446 no . . .
C19 C24 H24 120.397 no . . .
C23 C24 H24 120.385 no . . .
C22 C25 H25A 109.477 no . . .
C22 C25 H25B 109.476 no . . .
C22 C25 H25C 109.470 no . . .
H25A C25 H25B 109.473 no . . .
H25A C25 H25C 109.459 no . . .
H25B C25 H25C 109.472 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 S1 N1 C1 -40.54(12) no . . . .
O2 S1 N1 C12 157.07(9) no . . . .
O2 S1 C19 C20 -162.30(11) no . . . .
O2 S1 C19 C24 22.82(14) no . . . .
O3 S1 N1 C1 -170.28(10) no . . . .
O3 S1 N1 C12 27.33(12) no . . . .
O3 S1 C19 C20 -29.91(14) no . . . .
O3 S1 C19 C24 155.21(11) no . . . .
N1 S1 C19 C20 82.95(12) no . . . .
N1 S1 C19 C24 -91.93(12) no . . . .
C19 S1 N1 C1 74.99(12) no . . . .
C19 S1 N1 C12 -87.39(11) no . . . .
C7 O1 C9 C10 -63.87(17) no . . . .
C9 O1 C7 C6 -69.61(16) no . . . .
C9 O1 C7 C8 165.27(11) no . . . .
S1 N1 C1 C2 -79.47(17) no . . . .
S1 N1 C1 C6 105.13(15) no . . . .
S1 N1 C12 C11 -89.37(14) no . . . .
C1 N1 C12 C11 107.93(15) no . . . .
C12 N1 C1 C2 83.08(18) no . . . .
C12 N1 C1 C6 -92.33(17) no . . . .
N1 C1 C2 C3 -178.13(14) no . . . .
N1 C1 C6 C5 177.47(13) no . . . .
N1 C1 C6 C7 3.7(3) no . . . .
C2 C1 C6 C5 2.1(3) no . . . .
C2 C1 C6 C7 -171.71(14) no . . . .
C6 C1 C2 C3 -2.8(3) no . . . .
C1 C2 C3 C4 1.2(3) no . . . .
C2 C3 C4 C5 1.1(3) no . . . .
C3 C4 C5 C6 -1.7(3) no . . . .
C4 C5 C6 C1 0.1(3) no . . . .
C4 C5 C6 C7 173.84(16) no . . . .
C1 C6 C7 O1 104.90(17) no . . . .
C1 C6 C7 C8 -135.89(15) no . . . .
C5 C6 C7 O1 -68.7(2) no . . . .
C5 C6 C7 C8 50.5(3) no . . . .
O1 C7 C8 F1 174.60(14) no . . . .
O1 C7 C8 F2 52.54(19) no . . . .
O1 C7 C8 F3 -66.77(18) no . . . .
C6 C7 C8 F1 51.3(2) no . . . .
C6 C7 C8 F2 -70.8(2) no . . . .
C6 C7 C8 F3 169.89(14) no . . . .
O1 C9 C10 C11 100.56(17) no . . . .
O1 C9 C10 C13 -78.26(17) no . . . .
C9 C10 C11 C12 2.9(3) no . . . .
C9 C10 C13 C14 28.1(3) no . . . .
C9 C10 C13 C18 -150.20(14) no . . . .
C11 C10 C13 C14 -150.71(15) no . . . .
C11 C10 C13 C18 31.0(3) no . . . .
C13 C10 C11 C12 -178.29(14) no . . . .
C10 C11 C12 N1 -79.2(2) no . . . .
C10 C13 C14 C15 -179.85(14) no . . . .
C10 C13 C18 C17 -179.80(14) no . . . .
C14 C13 C18 C17 1.8(3) no . . . .
C18 C13 C14 C15 -1.5(3) no . . . .
C13 C14 C15 C16 0.2(3) no . . . .
C14 C15 C16 C17 0.8(3) no . . . .
C15 C16 C17 C18 -0.4(3) no . . . .
C16 C17 C18 C13 -0.9(3) no . . . .
S1 C19 C20 C21 -173.34(11) no . . . .
S1 C19 C24 C23 173.04(11) no . . . .
C20 C19 C24 C23 -1.8(3) no . . . .
C24 C19 C20 C21 1.5(3) no . . . .
C19 C20 C21 C22 0.5(3) no . . . .
C20 C21 C22 C23 -2.0(3) no . . . .
C20 C21 C22 C25 175.30(14) no . . . .
C21 C22 C23 C24 1.7(3) no . . . .
C25 C22 C23 C24 -175.66(15) no . . . .
C22 C23 C24 C19 0.2(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 C2 3.4110(18) no . .
S1 C11 3.4932(18) no . .
F1 O1 3.5200(19) no . .
F1 O2 3.554(2) no . .
F1 C5 3.341(3) no . .
F1 C6 2.874(3) no . .
F2 O1 2.687(2) no . .
F2 C5 3.047(3) no . .
F2 C6 3.097(3) no . .
F3 O1 2.7538(19) no . .
O1 C1 3.400(2) no . .
O1 C5 3.124(3) no . .
O1 C11 3.371(3) no . .
O1 C13 3.222(2) no . .
O1 C14 3.128(3) no . .
O2 C1 2.933(2) no . .
O2 C6 3.479(3) no . .
O2 C24 2.943(2) no . .
O3 C11 3.171(3) no . .
O3 C12 2.825(3) no . .
O3 C20 2.988(2) no . .
N1 C7 2.858(3) no . .
N1 C9 3.468(3) no . .
N1 C10 3.284(3) no . .
N1 C20 3.466(3) no . .
N1 C24 3.542(3) no . .
C1 C4 2.775(3) no . .
C1 C9 3.462(3) no . .
C1 C11 3.500(3) no . .
C1 C19 3.397(3) no . .
C2 C5 2.779(3) no . .
C2 C12 3.301(3) no . .
C2 C19 3.412(3) no . .
C2 C24 3.342(3) no . .
C3 C6 2.799(3) no . .
C5 C8 3.091(3) no . .
C6 C9 3.017(3) no . .
C6 C12 3.374(3) no . .
C7 C10 2.982(3) no . .
C7 C11 3.388(3) no . .
C7 C12 3.514(3) no . .
C9 C12 3.040(3) no . .
C9 C14 2.955(3) no . .
C11 C18 2.967(3) no . .
C12 C19 3.546(3) no . .
C13 C16 2.803(3) no . .
C14 C17 2.773(3) no . .
C15 C18 2.771(3) no . .
C19 C22 2.787(3) no . .
C20 C23 2.774(3) no . .
C21 C24 2.778(3) no . .
F1 C11 3.272(3) no . 7_746
F1 C12 3.293(3) no . 7_746
F2 C19 3.254(3) no . 3_555
F2 C24 3.355(3) no . 3_555
F3 C16 3.415(3) no . 2_745
F3 C23 3.337(3) no . 8_556
O2 C9 3.460(3) no . 7_746
O2 C10 3.345(3) no . 7_746
O2 C13 3.467(2) no . 7_746
O3 C20 3.357(3) no . 5_766
O3 C21 3.402(3) no . 5_766
C9 O2 3.460(3) no . 7_756
C9 C25 3.558(3) no . 4_665
C10 O2 3.345(3) no . 7_756
C11 F1 3.272(3) no . 7_756
C12 F1 3.293(3) no . 7_756
C12 C16 3.535(3) no . 8_456
C13 O2 3.467(2) no . 7_756
C15 C21 3.441(3) no . 8_556
C15 C24 3.577(3) no . 7_756
C16 F3 3.415(3) no . 2_755
C16 C12 3.535(3) no . 8_556
C16 C23 3.476(3) no . 7_756
C16 C24 3.525(3) no . 7_756
C17 C24 3.597(3) no . 7_756
C19 F2 3.254(3) no . 3_554
C20 O3 3.357(3) no . 5_766
C21 O3 3.402(3) no . 5_766
C21 C15 3.441(3) no . 8_456
C23 F3 3.337(3) no . 8_456
C23 C16 3.476(3) no . 7_746
C24 F2 3.355(3) no . 3_554
C24 C15 3.577(3) no . 7_746
C24 C16 3.525(3) no . 7_746
C24 C17 3.597(3) no . 7_746
C25 C9 3.558(3) no . 4_664
S1 H2 3.3476 no . .
S1 H7 3.2113 no . .
S1 H12A 3.4734 no . .
S1 H12B 2.7351 no . .
S1 H20 2.8451 no . .
S1 H24 2.8335 no . .
F1 H5 3.2327 no . .
F1 H7 2.6440 no . .
F2 H5 2.4262 no . .
F2 H7 3.2113 no . .
F3 H7 2.4845 no . .
F3 H14 3.2423 no . .
O1 H5 3.0885 no . .
O1 H14 2.4616 no . .
O2 H7 3.1706 no . .
O2 H24 2.5794 no . .
O3 H11 2.9571 no . .
O3 H12B 2.5949 no . .
O3 H20 2.6501 no . .
N1 H2 2.6272 no . .
N1 H7 2.3553 no . .
N1 H9B 3.0517 no . .
N1 H11 3.0573 no . .
N1 H20 3.4851 no . .
C1 H3 3.2692 no . .
C1 H5 3.2650 no . .
C1 H7 2.5496 no . .
C1 H9B 2.8724 no . .
C1 H12A 2.5322 no . .
C1 H12B 3.2069 no . .
C1 H24 3.5345 no . .
C2 H4 3.2585 no . .
C2 H12A 3.0559 no . .
C2 H24 3.2742 no . .
C3 H5 3.2589 no . .
C4 H2 3.2591 no . .
C5 H3 3.2615 no . .
C5 H7 3.3351 no . .
C5 H9B 3.4275 no . .
C6 H2 3.2827 no . .
C6 H4 3.2758 no . .
C6 H9B 2.6710 no . .
C6 H12A 3.3400 no . .
C7 H5 2.7039 no . .
C7 H9A 3.2393 no . .
C7 H9B 2.6012 no . .
C7 H14 3.4803 no . .
C8 H5 2.8588 no . .
C9 H7 2.5393 no . .
C9 H11 3.3343 no . .
C9 H12A 2.8264 no . .
C9 H14 2.6363 no . .
C10 H7 2.5630 no . .
C10 H12A 2.7277 no . .
C10 H12B 3.2884 no . .
C10 H14 2.6693 no . .
C10 H18 2.6753 no . .
C11 H7 2.7159 no . .
C11 H9A 3.1944 no . .
C11 H9B 2.5778 no . .
C11 H18 2.7149 no . .
C12 H2 3.3008 no . .
C12 H7 2.9746 no . .
C12 H9B 2.6107 no . .
C12 H20 3.4454 no . .
C13 H7 3.4951 no . .
C13 H9A 2.6663 no . .
C13 H9B 3.3579 no . .
C13 H11 2.5683 no . .
C13 H15 3.2775 no . .
C13 H17 3.2786 no . .
C14 H9A 2.8453 no . .
C14 H16 3.2659 no . .
C14 H18 3.2640 no . .
C15 H17 3.2479 no . .
C16 H14 3.2619 no . .
C16 H18 3.2625 no . .
C17 H15 3.2479 no . .
C18 H11 2.6427 no . .
C18 H14 3.2643 no . .
C18 H16 3.2666 no . .
C19 H2 2.9111 no . .
C19 H12B 3.2319 no . .
C19 H21 3.2537 no . .
C19 H23 3.2540 no . .
C20 H2 3.5084 no . .
C20 H12B 3.0917 no . .
C20 H24 3.2722 no . .
C21 H23 3.2533 no . .
C21 H25A 3.3142 no . .
C21 H25B 2.7707 no . .
C21 H25C 2.7707 no . .
C22 H20 3.2733 no . .
C22 H24 3.2790 no . .
C23 H2 3.3917 no . .
C23 H21 3.2537 no . .
C23 H25A 2.5525 no . .
C23 H25B 3.1232 no . .
C23 H25C 3.1521 no . .
C24 H2 2.8627 no . .
C24 H20 3.2714 no . .
C25 H21 2.6772 no . .
C25 H23 2.6645 no . .
H2 H3 2.3415 no . .
H2 H12A 3.0814 no . .
H2 H12B 3.5037 no . .
H2 H24 3.0465 no . .
H3 H4 2.3314 no . .
H4 H5 2.3319 no . .
H7 H9A 3.4644 no . .
H7 H9B 2.7845 no . .
H7 H11 3.3003 no . .
H7 H12A 3.4011 no . .
H7 H14 3.4945 no . .
H9A H12A 3.4994 no . .
H9A H14 2.5269 no . .
H9B H11 3.5125 no . .
H9B H12A 2.1443 no . .
H9B H12B 3.5359 no . .
H11 H12A 2.8067 no . .
H11 H12B 2.2825 no . .
H11 H18 2.2154 no . .
H12B H20 2.6348 no . .
H14 H15 2.3347 no . .
H15 H16 2.3307 no . .
H16 H17 2.3335 no . .
H17 H18 2.3355 no . .
H20 H21 2.3313 no . .
H21 H25B 2.7423 no . .
H21 H25C 2.7024 no . .
H23 H24 2.3359 no . .
H23 H25A 2.3355 no . .
H23 H25B 3.3180 no . .
H23 H25C 3.3339 no . .
F1 H11 3.2413 no . 7_746
F1 H12A 3.1534 no . 7_746
F1 H12B 2.9299 no . 7_746
F1 H16 3.0156 no . 2_745
F2 H9A 2.9006 no . 5_767
F2 H24 3.4917 no . 3_555
F3 H3 3.5113 no . 8_556
F3 H16 2.7826 no . 2_745
F3 H17 3.4080 no . 2_745
F3 H23 2.7789 no . 8_556
F3 H25A 3.3036 no . 8_556
O1 H25B 3.3089 no . 4_665
O2 H9A 2.9032 no . 7_746
O2 H9B 3.5986 no . 7_746
O3 H3 3.4890 no . 8_556
O3 H4 3.0492 no . 8_556
O3 H20 2.7022 no . 5_766
O3 H21 2.7862 no . 5_766
C3 H17 3.2469 no . 7_746
C3 H21 3.4629 no . 4_665
C4 H15 3.3142 no . 5_767
C4 H21 3.1467 no . 4_665
C4 H23 3.5104 no . 3_555
C4 H25B 3.3548 no . 4_665
C5 H15 3.3489 no . 5_767
C5 H23 3.5971 no . 3_555
C5 H25B 3.0997 no . 4_665
C6 H25B 3.4098 no . 4_665
C8 H16 3.4442 no . 2_745
C9 H25A 3.3481 no . 4_665
C9 H25B 3.0539 no . 4_665
C10 H3 3.4784 no . 8_556
C11 H3 3.3650 no . 8_556
C11 H21 3.1949 no . 5_766
C12 H16 3.1229 no . 8_456
C13 H2 3.4301 no . 8_556
C13 H3 3.3517 no . 8_556
C13 H24 2.9039 no . 7_756
C14 H2 3.1411 no . 8_556
C14 H5 3.4563 no . 5_767
C14 H24 2.9666 no . 7_756
C15 H2 2.9944 no . 8_556
C15 H4 3.5980 no . 5_767
C15 H5 3.2755 no . 5_767
C15 H21 3.5494 no . 8_556
C15 H23 3.0310 no . 7_756
C15 H24 2.9753 no . 7_756
C16 H2 3.1524 no . 8_556
C16 H12A 2.9481 no . 8_556
C16 H12B 3.2484 no . 8_556
C16 H23 2.8018 no . 7_756
C16 H24 2.9154 no . 7_756
C17 H2 3.4424 no . 8_556
C17 H12A 3.0170 no . 8_556
C17 H23 3.5153 no . 7_756
C17 H24 2.8190 no . 7_756
C17 H25C 2.9156 no . 5_766
C18 H2 3.5785 no . 8_556
C18 H24 2.8013 no . 7_756
C18 H25C 2.8493 no . 5_766
C20 H11 3.4567 no . 5_766
C20 H12B 3.3386 no . 5_766
C20 H15 3.1429 no . 8_456
C20 H20 3.1316 no . 5_766
C21 H11 2.8574 no . 5_766
C21 H15 2.6455 no . 8_456
C21 H18 3.5191 no . 5_766
C22 H5 3.5698 no . 3_554
C22 H15 3.0531 no . 8_456
C22 H18 3.4949 no . 5_766
C23 H4 3.3470 no . 3_554
C23 H5 3.0193 no . 3_554
C23 H16 3.5418 no . 7_746
C24 H5 3.2424 no . 3_554
C25 H4 3.5084 no . 3_554
C25 H9A 3.3831 no . 4_664
C25 H9B 2.8966 no . 4_664
C25 H15 3.4871 no . 8_456
C25 H17 3.4210 no . 5_766
C25 H18 3.2801 no . 5_766
H2 C13 3.4301 no . 8_456
H2 C14 3.1411 no . 8_456
H2 C15 2.9944 no . 8_456
H2 C16 3.1524 no . 8_456
H2 C17 3.4424 no . 8_456
H2 C18 3.5785 no . 8_456
H2 H14 3.5719 no . 8_456
H2 H15 3.3515 no . 8_456
H2 H16 3.5791 no . 8_456
H3 F3 3.5113 no . 8_456
H3 O3 3.4890 no . 8_456
H3 C10 3.4784 no . 8_456
H3 C11 3.3650 no . 8_456
H3 C13 3.3517 no . 8_456
H3 H7 3.0169 no . 8_456
H3 H11 3.0617 no . 8_456
H3 H17 3.1301 no . 7_746
H3 H21 3.4219 no . 4_665
H4 O3 3.0492 no . 8_456
H4 C15 3.5980 no . 5_767
H4 C23 3.3470 no . 3_555
H4 C25 3.5084 no . 3_555
H4 H15 2.8800 no . 5_767
H4 H21 2.8745 no . 4_665
H4 H23 2.8536 no . 3_555
H4 H25A 2.9882 no . 3_555
H4 H25C 3.4517 no . 3_555
H5 C14 3.4563 no . 5_767
H5 C15 3.2755 no . 5_767
H5 C22 3.5698 no . 3_555
H5 C23 3.0193 no . 3_555
H5 C24 3.2424 no . 3_555
H5 H14 3.2562 no . 5_767
H5 H15 2.9283 no . 5_767
H5 H23 3.0363 no . 3_555
H5 H24 3.4028 no . 3_555
H5 H25B 3.2654 no . 4_665
H7 H3 3.0169 no . 8_556
H9A F2 2.9006 no . 5_767
H9A O2 2.9032 no . 7_756
H9A C25 3.3831 no . 4_665
H9A H25A 2.9338 no . 4_665
H9A H25B 3.0162 no . 4_665
H9B O2 3.5986 no . 7_756
H9B C25 2.8966 no . 4_665
H9B H25A 2.8534 no . 4_665
H9B H25B 2.4641 no . 4_665
H9B H25C 2.8943 no . 4_665
H11 F1 3.2413 no . 7_756
H11 C20 3.4567 no . 5_766
H11 C21 2.8574 no . 5_766
H11 H3 3.0617 no . 8_556
H11 H20 3.4264 no . 5_766
H11 H21 2.3031 no . 5_766
H11 H25C 3.5144 no . 5_766
H12A F1 3.1534 no . 7_756
H12A C16 2.9481 no . 8_456
H12A C17 3.0170 no . 8_456
H12A H16 2.6845 no . 8_456
H12A H17 2.8122 no . 8_456
H12A H25C 3.5381 no . 4_665
H12B F1 2.9299 no . 7_756
H12B C16 3.2484 no . 8_456
H12B C20 3.3386 no . 5_766
H12B H16 2.6546 no . 8_456
H12B H20 2.8089 no . 5_766
H12B H21 3.4196 no . 5_766
H14 H2 3.5719 no . 8_556
H14 H5 3.2562 no . 5_767
H14 H24 3.5482 no . 7_756
H14 H25B 3.0173 no . 8_556
H15 C4 3.3142 no . 5_767
H15 C5 3.3489 no . 5_767
H15 C20 3.1429 no . 8_556
H15 C21 2.6455 no . 8_556
H15 C22 3.0531 no . 8_556
H15 C25 3.4871 no . 8_556
H15 H2 3.3515 no . 8_556
H15 H4 2.8800 no . 5_767
H15 H5 2.9283 no . 5_767
H15 H20 3.4344 no . 8_556
H15 H21 2.6392 no . 8_556
H15 H23 3.0910 no . 7_756
H15 H24 3.5625 no . 7_756
H15 H25B 2.9336 no . 8_556
H16 F1 3.0156 no . 2_755
H16 F3 2.7826 no . 2_755
H16 C8 3.4442 no . 2_755
H16 C12 3.1229 no . 8_556
H16 C23 3.5418 no . 7_756
H16 H2 3.5791 no . 8_556
H16 H12A 2.6845 no . 8_556
H16 H12B 2.6546 no . 8_556
H16 H20 3.5743 no . 8_556
H16 H23 2.7153 no . 7_756
H16 H24 3.4857 no . 7_756
H17 F3 3.4080 no . 2_755
H17 C3 3.2469 no . 7_756
H17 C25 3.4210 no . 5_766
H17 H3 3.1301 no . 7_756
H17 H12A 2.8122 no . 8_556
H17 H24 3.3448 no . 7_756
H17 H25A 3.5142 no . 5_766
H17 H25C 2.5427 no . 5_766
H18 C21 3.5191 no . 5_766
H18 C22 3.4949 no . 5_766
H18 C25 3.2801 no . 5_766
H18 H21 3.2546 no . 5_766
H18 H24 3.3097 no . 7_756
H18 H25C 2.4214 no . 5_766
H20 O3 2.7022 no . 5_766
H20 C20 3.1316 no . 5_766
H20 H11 3.4264 no . 5_766
H20 H12B 2.8089 no . 5_766
H20 H15 3.4344 no . 8_456
H20 H16 3.5743 no . 8_456
H20 H20 2.1992 no . 5_766
H21 O3 2.7862 no . 5_766
H21 C3 3.4629 no . 4_664
H21 C4 3.1467 no . 4_664
H21 C11 3.1949 no . 5_766
H21 C15 3.5494 no . 8_456
H21 H3 3.4219 no . 4_664
H21 H4 2.8745 no . 4_664
H21 H11 2.3031 no . 5_766
H21 H12B 3.4196 no . 5_766
H21 H15 2.6392 no . 8_456
H21 H18 3.2546 no . 5_766
H23 F3 2.7789 no . 8_456
H23 C4 3.5104 no . 3_554
H23 C5 3.5971 no . 3_554
H23 C15 3.0310 no . 7_746
H23 C16 2.8018 no . 7_746
H23 C17 3.5153 no . 7_746
H23 H4 2.8536 no . 3_554
H23 H5 3.0363 no . 3_554
H23 H15 3.0910 no . 7_746
H23 H16 2.7153 no . 7_746
H24 F2 3.4917 no . 3_554
H24 C13 2.9039 no . 7_746
H24 C14 2.9666 no . 7_746
H24 C15 2.9753 no . 7_746
H24 C16 2.9154 no . 7_746
H24 C17 2.8190 no . 7_746
H24 C18 2.8013 no . 7_746
H24 H5 3.4028 no . 3_554
H24 H14 3.5482 no . 7_746
H24 H15 3.5625 no . 7_746
H24 H16 3.4857 no . 7_746
H24 H17 3.3448 no . 7_746
H24 H18 3.3097 no . 7_746
H25A F3 3.3036 no . 8_456
H25A C9 3.3481 no . 4_664
H25A H4 2.9882 no . 3_554
H25A H9A 2.9338 no . 4_664
H25A H9B 2.8534 no . 4_664
H25A H17 3.5142 no . 5_766
H25B O1 3.3089 no . 4_664
H25B C4 3.3548 no . 4_664
H25B C5 3.0997 no . 4_664
H25B C6 3.4098 no . 4_664
H25B C9 3.0539 no . 4_664
H25B H5 3.2654 no . 4_664
H25B H9A 3.0162 no . 4_664
H25B H9B 2.4641 no . 4_664
H25B H14 3.0173 no . 8_456
H25B H15 2.9336 no . 8_456
H25C C17 2.9156 no . 5_766
H25C C18 2.8493 no . 5_766
H25C H4 3.4517 no . 3_554
H25C H9B 2.8943 no . 4_664
H25C H11 3.5144 no . 5_766
H25C H12A 3.5381 no . 4_664
H25C H17 2.5427 no . 5_766
H25C H18 2.4214 no . 5_766

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20170926-sample2
_database_code_depnum_ccdc_archive 'CCDC 1589030'
_audit_update_record             
;
2017-12-03 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H22 F3 N O4 S'
_chemical_formula_moiety         'C25 H22 F3 N O4 S'
_chemical_formula_weight         489.51
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_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
#------------------------------------------------------------------------------
_cell_length_a                   16.8716(4)
_cell_length_b                   7.8975(2)
_cell_length_c                   16.7075(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.3044(10)
_cell_angle_gamma                90.0000
_cell_volume                     2226.13(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6414
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016.00
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.960

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            16650
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             5072
_reflns_number_gt                4728
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0928
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5072
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0505P)²+0.7087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.360
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.720539(16) 0.12031(4) 0.484136(17) 0.02105(9) Uani 1.0 4 d . . .
F1 F 0.69758(6) -0.13777(12) 0.25711(5) 0.0438(3) Uani 1.0 4 d . . .
F2 F 0.81726(5) -0.20171(11) 0.22453(5) 0.0394(2) Uani 1.0 4 d . . .
F3 F 0.72978(5) -0.39688(10) 0.23520(4) 0.03456(19) Uani 1.0 4 d . . .
O1 O 0.83613(5) -0.39384(10) 0.36008(5) 0.02188(18) Uani 1.0 4 d . . .
O2 O 0.95609(5) -0.23813(11) 0.53359(5) 0.02442(19) Uani 1.0 4 d . . .
O3 O 0.78774(5) 0.22994(12) 0.49023(6) 0.0303(2) Uani 1.0 4 d . . .
O4 O 0.67291(5) 0.11452(11) 0.41269(5) 0.0274(2) Uani 1.0 4 d . . .
N1 N 0.75443(6) -0.07217(12) 0.49742(6) 0.0201(2) Uani 1.0 4 d . . .
C1 C 0.66097(7) -0.44502(15) 0.39912(7) 0.0239(3) Uani 1.0 4 d . . .
C2 C 0.60659(7) -0.49326(16) 0.45675(8) 0.0265(3) Uani 1.0 4 d . . .
C3 C 0.60125(7) -0.40436(16) 0.52815(8) 0.0277(3) Uani 1.0 4 d . . .
C4 C 0.64874(7) -0.26409(16) 0.54127(7) 0.0243(3) Uani 1.0 4 d . . .
C5 C 0.70200(6) -0.21270(14) 0.48227(7) 0.0199(3) Uani 1.0 4 d . . .
C6 C 0.70938(6) -0.30374(14) 0.41121(7) 0.0198(3) Uani 1.0 4 d . . .
C7 C 0.77746(7) -0.26508(14) 0.35579(7) 0.0199(3) Uani 1.0 4 d . . .
C8 C 0.75515(8) -0.25191(16) 0.26808(7) 0.0267(3) Uani 1.0 4 d . . .
C9 C 0.87487(7) -0.40465(15) 0.43664(7) 0.0212(3) Uani 1.0 4 d . . .
C10 C 0.92614(6) -0.25031(14) 0.45193(6) 0.0191(3) Uani 1.0 4 d . . .
C11 C 0.90136(7) -0.11008(15) 0.50489(7) 0.0208(3) Uani 1.0 4 d . . .
C12 C 0.82369(7) -0.10339(16) 0.55009(7) 0.0224(3) Uani 1.0 4 d . . .
C13 C 0.98784(6) -0.21842(15) 0.38910(7) 0.0197(3) Uani 1.0 4 d . . .
C14 C 1.04547(7) -0.34196(15) 0.37623(7) 0.0242(3) Uani 1.0 4 d . . .
C15 C 1.10271(7) -0.31784(17) 0.31762(8) 0.0287(3) Uani 1.0 4 d . . .
C16 C 1.10307(7) -0.17114(19) 0.27236(8) 0.0301(3) Uani 1.0 4 d . . .
C17 C 1.04653(7) -0.04736(18) 0.28555(8) 0.0299(3) Uani 1.0 4 d . . .
C18 C 0.98863(7) -0.07135(16) 0.34362(7) 0.0247(3) Uani 1.0 4 d . . .
C19 C 0.65644(7) 0.16457(14) 0.56487(7) 0.0210(3) Uani 1.0 4 d . . .
C20 C 0.68749(7) 0.22772(15) 0.63605(7) 0.0252(3) Uani 1.0 4 d . . .
C21 C 0.63720(8) 0.25554(16) 0.70039(8) 0.0282(3) Uani 1.0 4 d . . .
C22 C 0.55627(8) 0.22187(16) 0.69416(8) 0.0281(3) Uani 1.0 4 d . . .
C23 C 0.52605(7) 0.16107(16) 0.62184(8) 0.0273(3) Uani 1.0 4 d . . .
C24 C 0.57551(7) 0.13185(15) 0.55720(7) 0.0242(3) Uani 1.0 4 d . . .
C25 C 0.50222(10) 0.2500(2) 0.76476(9) 0.0415(4) Uani 1.0 4 d . . .
H1 H 0.6652 -0.5072 0.3521 0.0287 Uiso 1.0 4 calc R . .
H2 H 0.5736 -0.5856 0.4475 0.0318 Uiso 1.0 4 calc R . .
H3 H 0.5657 -0.4391 0.5672 0.0332 Uiso 1.0 4 calc R . .
H4 H 0.6452 -0.2044 0.5891 0.0292 Uiso 1.0 4 calc R . .
H5 H 0.8016 -0.1578 0.3725 0.0239 Uiso 1.0 4 calc R . .
H6A H 0.9075 -0.5057 0.4385 0.0255 Uiso 1.0 4 calc R . .
H7B H 0.8353 -0.4137 0.4783 0.0255 Uiso 1.0 4 calc R . .
H8 H 1.0457 -0.4404 0.4068 0.0291 Uiso 1.0 4 calc R . .
H9 H 1.1409 -0.4007 0.3089 0.0345 Uiso 1.0 4 calc R . .
H10 H 1.1413 -0.1557 0.2331 0.0362 Uiso 1.0 4 calc R . .
H11 H 1.0472 0.0519 0.2556 0.0359 Uiso 1.0 4 calc R . .
H12 H 0.9504 0.0115 0.3519 0.0296 Uiso 1.0 4 calc R . .
H13 H 0.9252 0.0002 0.4930 0.0250 Uiso 1.0 4 calc R . .
H14B H 0.8267 -0.0143 0.5899 0.0269 Uiso 1.0 4 calc R . .
H15A H 0.8161 -0.2098 0.5780 0.0269 Uiso 1.0 4 calc R . .
H16 H 0.7413 0.2511 0.6406 0.0303 Uiso 1.0 4 calc R . .
H17 H 0.6578 0.2972 0.7482 0.0338 Uiso 1.0 4 calc R . .
H18 H 0.4720 0.1398 0.6169 0.0328 Uiso 1.0 4 calc R . .
H19 H 0.5549 0.0909 0.5092 0.0290 Uiso 1.0 4 calc R . .
H20B H 0.4798 0.1437 0.7811 0.0498 Uiso 1.0 4 calc R . .
H21C H 0.4604 0.3263 0.7497 0.0498 Uiso 1.0 4 calc R . .
H22A H 0.5321 0.2977 0.8083 0.0498 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O3 1.4298(10) yes . .
S1 O4 1.4361(9) yes . .
S1 N1 1.6388(10) yes . .
S1 C19 1.7682(12) yes . .
F1 C8 1.3370(17) yes . .
F2 C8 1.3389(16) yes . .
F3 C8 1.3391(15) yes . .
O1 C7 1.4207(14) yes . .
O1 C9 1.4359(15) yes . .
O2 C10 1.4556(13) yes . .
O2 C11 1.4493(15) yes . .
N1 C5 1.4408(15) yes . .
N1 C12 1.4798(16) yes . .
C1 C2 1.3869(18) yes . .
C1 C6 1.3968(16) yes . .
C2 C3 1.3875(19) yes . .
C3 C4 1.3840(18) yes . .
C4 C5 1.3976(17) yes . .
C5 C6 1.3941(17) yes . .
C6 C7 1.5104(16) yes . .
C7 C8 1.5146(17) yes . .
C9 C10 1.5155(16) yes . .
C10 C11 1.4792(16) yes . .
C10 C13 1.5035(15) yes . .
C11 C12 1.5168(17) yes . .
C13 C14 1.3949(17) yes . .
C13 C18 1.3881(17) yes . .
C14 C15 1.3921(18) yes . .
C15 C16 1.384(2) yes . .
C16 C17 1.3843(19) yes . .
C17 C18 1.3934(18) yes . .
C19 C20 1.3895(17) yes . .
C19 C24 1.3949(17) yes . .
C20 C21 1.3905(18) yes . .
C21 C22 1.3944(19) yes . .
C22 C23 1.3942(19) yes . .
C22 C25 1.511(2) yes . .
C23 C24 1.3876(18) yes . .
C1 H1 0.930 no . .
C2 H2 0.930 no . .
C3 H3 0.930 no . .
C4 H4 0.930 no . .
C7 H5 0.980 no . .
C9 H6A 0.970 no . .
C9 H7B 0.970 no . .
C11 H13 0.980 no . .
C12 H14B 0.970 no . .
C12 H15A 0.970 no . .
C14 H8 0.930 no . .
C15 H9 0.930 no . .
C16 H10 0.930 no . .
C17 H11 0.930 no . .
C18 H12 0.930 no . .
C20 H16 0.930 no . .
C21 H17 0.930 no . .
C23 H18 0.930 no . .
C24 H19 0.930 no . .
C25 H20B 0.960 no . .
C25 H21C 0.960 no . .
C25 H22A 0.960 no . .

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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O3 S1 O4 121.23(6) yes . . .
O3 S1 N1 106.03(6) yes . . .
O3 S1 C19 108.30(6) yes . . .
O4 S1 N1 106.04(6) yes . . .
O4 S1 C19 107.37(6) yes . . .
N1 S1 C19 107.12(6) yes . . .
C7 O1 C9 113.66(9) yes . . .
C10 O2 C11 61.22(8) yes . . .
S1 N1 C5 118.51(8) yes . . .
S1 N1 C12 120.59(8) yes . . .
C5 N1 C12 117.28(10) yes . . .
C2 C1 C6 120.50(11) yes . . .
C1 C2 C3 120.27(12) yes . . .
C2 C3 C4 120.07(12) yes . . .
C3 C4 C5 119.64(11) yes . . .
N1 C5 C4 119.75(11) yes . . .
N1 C5 C6 119.30(10) yes . . .
C4 C5 C6 120.77(11) yes . . .
C1 C6 C5 118.71(11) yes . . .
C1 C6 C7 121.25(11) yes . . .
C5 C6 C7 119.31(10) yes . . .
O1 C7 C6 110.87(9) yes . . .
O1 C7 C8 105.51(10) yes . . .
C6 C7 C8 114.91(10) yes . . .
F1 C8 F2 107.21(10) yes . . .
F1 C8 F3 106.85(11) yes . . .
F1 C8 C7 110.83(10) yes . . .
F2 C8 F3 106.24(10) yes . . .
F2 C8 C7 110.79(11) yes . . .
F3 C8 C7 114.55(10) yes . . .
O1 C9 C10 111.04(9) yes . . .
O2 C10 C9 113.96(9) yes . . .
O2 C10 C11 59.18(7) yes . . .
O2 C10 C13 113.90(9) yes . . .
C9 C10 C11 122.69(10) yes . . .
C9 C10 C13 114.44(10) yes . . .
C11 C10 C13 119.42(10) yes . . .
O2 C11 C10 59.60(7) yes . . .
O2 C11 C12 114.22(10) yes . . .
C10 C11 C12 124.86(11) yes . . .
N1 C12 C11 113.04(10) yes . . .
C10 C13 C14 118.44(11) yes . . .
C10 C13 C18 122.08(10) yes . . .
C14 C13 C18 119.48(11) yes . . .
C13 C14 C15 119.96(11) yes . . .
C14 C15 C16 120.27(12) yes . . .
C15 C16 C17 119.95(12) yes . . .
C16 C17 C18 120.07(13) yes . . .
C13 C18 C17 120.25(12) yes . . .
S1 C19 C20 119.64(9) yes . . .
S1 C19 C24 119.71(9) yes . . .
C20 C19 C24 120.63(11) yes . . .
C19 C20 C21 119.31(12) yes . . .
C20 C21 C22 120.89(12) yes . . .
C21 C22 C23 118.93(12) yes . . .
C21 C22 C25 120.56(13) yes . . .
C23 C22 C25 120.50(13) yes . . .
C22 C23 C24 120.87(12) yes . . .
C19 C24 C23 119.35(11) yes . . .
C2 C1 H1 119.745 no . . .
C6 C1 H1 119.757 no . . .
C1 C2 H2 119.870 no . . .
C3 C2 H2 119.857 no . . .
C2 C3 H3 119.969 no . . .
C4 C3 H3 119.964 no . . .
C3 C4 H4 120.170 no . . .
C5 C4 H4 120.187 no . . .
O1 C7 H5 108.452 no . . .
C6 C7 H5 108.451 no . . .
C8 C7 H5 108.448 no . . .
O1 C9 H6A 109.419 no . . .
O1 C9 H7B 109.430 no . . .
C10 C9 H6A 109.430 no . . .
C10 C9 H7B 109.427 no . . .
H6A C9 H7B 108.038 no . . .
O2 C11 H13 115.240 no . . .
C10 C11 H13 115.235 no . . .
C12 C11 H13 115.232 no . . .
N1 C12 H14B 108.975 no . . .
N1 C12 H15A 108.969 no . . .
C11 C12 H14B 108.980 no . . .
C11 C12 H15A 108.980 no . . .
H14B C12 H15A 107.769 no . . .
C13 C14 H8 120.014 no . . .
C15 C14 H8 120.021 no . . .
C14 C15 H9 119.861 no . . .
C16 C15 H9 119.865 no . . .
C15 C16 H10 120.026 no . . .
C17 C16 H10 120.020 no . . .
C16 C17 H11 119.966 no . . .
C18 C17 H11 119.963 no . . .
C13 C18 H12 119.872 no . . .
C17 C18 H12 119.879 no . . .
C19 C20 H16 120.345 no . . .
C21 C20 H16 120.345 no . . .
C20 C21 H17 119.554 no . . .
C22 C21 H17 119.552 no . . .
C22 C23 H18 119.562 no . . .
C24 C23 H18 119.568 no . . .
C19 C24 H19 120.331 no . . .
C23 C24 H19 120.321 no . . .
C22 C25 H20B 109.474 no . . .
C22 C25 H21C 109.469 no . . .
C22 C25 H22A 109.461 no . . .
H20B C25 H21C 109.479 no . . .
H20B C25 H22A 109.470 no . . .
H21C C25 H22A 109.474 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 S1 N1 C5 -170.53(7) no . . . .
O3 S1 N1 C12 31.51(9) no . . . .
O3 S1 C19 C20 -27.98(10) no . . . .
O3 S1 C19 C24 153.60(8) no . . . .
O4 S1 N1 C5 -40.45(9) no . . . .
O4 S1 N1 C12 161.59(7) no . . . .
O4 S1 C19 C20 -160.49(8) no . . . .
O4 S1 C19 C24 21.10(10) no . . . .
N1 S1 C19 C20 85.98(9) no . . . .
N1 S1 C19 C24 -92.44(9) no . . . .
C19 S1 N1 C5 73.99(8) no . . . .
C19 S1 N1 C12 -83.98(8) no . . . .
C7 O1 C9 C10 -68.43(11) no . . . .
C9 O1 C7 C6 -65.34(11) no . . . .
C9 O1 C7 C8 169.66(8) no . . . .
C10 O2 C11 C10 0.00(5) no . . . .
C10 O2 C11 C12 117.56(10) no . . . .
C11 O2 C10 C9 -115.03(10) no . . . .
C11 O2 C10 C11 0.00(6) no . . . .
C11 O2 C10 C13 111.17(10) no . . . .
S1 N1 C5 C4 -82.69(11) no . . . .
S1 N1 C5 C6 102.22(10) no . . . .
S1 N1 C12 C11 -94.89(10) no . . . .
C5 N1 C12 C11 106.89(11) no . . . .
C12 N1 C5 C4 76.01(12) no . . . .
C12 N1 C5 C6 -99.09(12) no . . . .
C2 C1 C6 C5 0.11(17) no . . . .
C2 C1 C6 C7 170.22(10) no . . . .
C6 C1 C2 C3 -1.83(18) no . . . .
C1 C2 C3 C4 1.78(18) no . . . .
C2 C3 C4 C5 -0.01(18) no . . . .
C3 C4 C5 N1 -176.75(10) no . . . .
C3 C4 C5 C6 -1.73(17) no . . . .
N1 C5 C6 C1 176.71(9) no . . . .
N1 C5 C6 C7 6.40(15) no . . . .
C4 C5 C6 C1 1.67(16) no . . . .
C4 C5 C6 C7 -168.64(10) no . . . .
C1 C6 C7 O1 -64.60(14) no . . . .
C1 C6 C7 C8 54.92(14) no . . . .
C5 C6 C7 O1 105.46(11) no . . . .
C5 C6 C7 C8 -135.03(10) no . . . .
O1 C7 C8 F1 177.66(9) no . . . .
O1 C7 C8 F2 -63.45(12) no . . . .
O1 C7 C8 F3 56.69(13) no . . . .
C6 C7 C8 F1 55.21(13) no . . . .
C6 C7 C8 F2 174.10(9) no . . . .
C6 C7 C8 F3 -65.76(14) no . . . .
O1 C9 C10 O2 169.78(8) no . . . .
O1 C9 C10 C11 102.18(11) no . . . .
O1 C9 C10 C13 -56.67(12) no . . . .
O2 C10 C11 O2 0.00(4) no . . . .
O2 C10 C11 C12 -99.84(11) no . . . .
O2 C10 C13 C14 72.55(12) no . . . .
O2 C10 C13 C18 -107.92(11) no . . . .
C9 C10 C11 O2 100.32(11) no . . . .
C9 C10 C11 C12 0.48(16) no . . . .
C9 C10 C13 C14 -61.02(13) no . . . .
C9 C10 C13 C18 118.50(11) no . . . .
C11 C10 C13 C14 139.38(10) no . . . .
C11 C10 C13 C18 -41.09(15) no . . . .
C13 C10 C11 O2 -101.84(10) no . . . .
C13 C10 C11 C12 158.32(9) no . . . .
O2 C11 C12 N1 -141.00(9) no . . . .
C10 C11 C12 N1 -72.28(14) no . . . .
C10 C13 C14 C15 178.94(9) no . . . .
C10 C13 C18 C17 -179.50(9) no . . . .
C14 C13 C18 C17 0.02(17) no . . . .
C18 C13 C14 C15 -0.60(17) no . . . .
C13 C14 C15 C16 0.46(18) no . . . .
C14 C15 C16 C17 0.27(19) no . . . .
C15 C16 C17 C18 -0.86(19) no . . . .
C16 C17 C18 C13 0.71(18) no . . . .
S1 C19 C20 C21 -177.33(7) no . . . .
S1 C19 C24 C23 177.64(7) no . . . .
C20 C19 C24 C23 -0.76(17) no . . . .
C24 C19 C20 C21 1.08(17) no . . . .
C19 C20 C21 C22 -0.38(18) no . . . .
C20 C21 C22 C23 -0.62(18) no . . . .
C20 C21 C22 C25 179.07(10) no . . . .
C21 C22 C23 C24 0.94(18) no . . . .
C25 C22 C23 C24 -178.75(11) no . . . .
C22 C23 C24 C19 -0.26(18) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 C4 3.4069(13) no . .
S1 C6 3.5683(12) no . .
S1 C11 3.5674(13) no . .
F1 O1 3.5314(13) no . .
F1 O4 3.3032(13) no . .
F1 C1 3.4517(15) no . .
F1 C6 2.8950(15) no . .
F2 O1 2.7432(12) no . .
F3 O1 2.7447(12) no . .
F3 C1 3.0044(14) no . .
F3 C6 3.0525(14) no . .
O1 C1 3.0566(15) no . .
O1 C5 3.3741(14) no . .
O1 C11 3.4725(15) no . .
O1 C13 2.9483(14) no . .
O1 C14 3.5644(15) no . .
O2 C14 3.1465(15) no . .
O2 C18 3.4826(15) no . .
O3 C11 3.3077(15) no . .
O3 C12 2.8795(16) no . .
O3 C20 2.9733(16) no . .
O4 C5 2.8748(14) no . .
O4 C6 3.3601(14) no . .
O4 C24 2.9310(15) no . .
N1 C7 2.8427(16) no . .
N1 C9 3.4752(16) no . .
N1 C10 3.3126(15) no . .
N1 C20 3.5039(16) no . .
N1 C24 3.5690(16) no . .
C1 C4 2.7803(17) no . .
C1 C8 3.1114(18) no . .
C2 C5 2.7704(17) no . .
C3 C6 2.7955(17) no . .
C4 C12 3.2156(17) no . .
C4 C19 3.4106(17) no . .
C4 C24 3.3732(18) no . .
C5 C9 3.3778(16) no . .
C5 C11 3.4784(16) no . .
C5 C19 3.3740(16) no . .
C6 C9 2.9324(16) no . .
C6 C12 3.3999(17) no . .
C7 C10 2.9738(16) no . .
C7 C11 3.4668(17) no . .
C7 C12 3.5708(17) no . .
C9 C12 3.1649(17) no . .
C9 C14 3.0950(17) no . .
C11 C18 3.0925(17) no . .
C12 C19 3.5368(17) no . .
C13 C16 2.7863(17) no . .
C14 C17 2.7765(19) no . .
C15 C18 2.7734(18) no . .
C19 C22 2.7867(18) no . .
C20 C23 2.7830(17) no . .
C21 C24 2.7811(18) no . .
F1 C21 3.3223(16) no . 4_554
F1 C25 3.503(2) no . 3_656
F2 C12 3.2982(15) no . 4_544
F2 C15 3.3941(16) no . 2_755
F2 C17 3.5729(16) no . 2_745
F3 C12 3.4824(14) no . 4_544
F3 C16 3.5587(16) no . 2_745
F3 C20 3.1729(14) no . 4_544
F3 C21 3.2850(16) no . 4_544
O1 C16 3.2816(17) no . 2_745
O1 C17 3.3705(16) no . 2_745
O2 C18 3.3214(15) no . 3_756
O3 C9 3.3622(15) no . 1_565
O4 C1 3.4917(15) no . 1_565
O4 C2 3.3760(16) no . 1_565
C1 O4 3.4917(15) no . 1_545
C2 O4 3.3760(16) no . 1_545
C2 C19 3.3551(17) no . 1_545
C2 C24 3.4448(18) no . 1_545
C3 C19 3.5815(17) no . 1_545
C9 O3 3.3622(15) no . 1_545
C11 C18 3.4430(17) no . 3_756
C12 F2 3.2982(15) no . 4_545
C12 F3 3.4824(14) no . 4_545
C14 C17 3.5074(18) no . 2_745
C15 F2 3.3941(16) no . 2_745
C15 C17 3.5427(18) no . 2_745
C16 F3 3.5587(16) no . 2_755
C16 O1 3.2816(17) no . 2_755
C17 F2 3.5729(16) no . 2_755
C17 O1 3.3705(16) no . 2_755
C17 C14 3.5074(18) no . 2_755
C17 C15 3.5427(18) no . 2_755
C18 O2 3.3214(15) no . 3_756
C18 C11 3.4430(17) no . 3_756
C19 C2 3.3551(17) no . 1_565
C19 C3 3.5815(17) no . 1_565
C20 F3 3.1729(14) no . 4_545
C21 F1 3.3223(16) no . 4_555
C21 F3 3.2850(16) no . 4_545
C24 C2 3.4448(18) no . 1_565
C25 F1 3.503(2) no . 3_656
S1 H4 3.3597 no . .
S1 H5 3.1938 no . .
S1 H13 3.5825 no . .
S1 H14B 2.7252 no . .
S1 H15A 3.4398 no . .
S1 H16 2.8312 no . .
S1 H19 2.8376 no . .
F1 H1 3.3670 no . .
F1 H5 2.6043 no . .
F2 H5 2.5113 no . .
F2 H12 3.5155 no . .
F3 H1 2.4043 no . .
F3 H5 3.2037 no . .
O1 H1 3.0215 no . .
O2 H6A 2.7656 no . .
O2 H7B 2.6281 no . .
O2 H8 3.0588 no . .
O2 H14B 2.9668 no . .
O2 H15A 2.4889 no . .
O3 H13 2.9442 no . .
O3 H14B 2.6295 no . .
O3 H16 2.6408 no . .
O4 H5 3.1311 no . .
O4 H19 2.5759 no . .
N1 H4 2.6192 no . .
N1 H5 2.3379 no . .
N1 H7B 3.0406 no . .
N1 H13 2.9380 no . .
N1 H16 3.5067 no . .
C1 H3 3.2436 no . .
C1 H5 3.3142 no . .
C1 H7B 3.2287 no . .
C2 H4 3.2410 no . .
C3 H1 3.2424 no . .
C4 H2 3.2385 no . .
C4 H7B 3.5280 no . .
C4 H15A 2.9187 no . .
C4 H19 3.2621 no . .
C5 H1 3.2423 no . .
C5 H3 3.2452 no . .
C5 H5 2.5316 no . .
C5 H7B 2.7543 no . .
C5 H14B 3.1743 no . .
C5 H15A 2.4970 no . .
C5 H19 3.4816 no . .
C6 H2 3.2538 no . .
C6 H4 3.2641 no . .
C6 H7B 2.5499 no . .
C6 H15A 3.3923 no . .
C7 H1 2.6916 no . .
C7 H6A 3.2096 no . .
C7 H7B 2.5499 no . .
C8 H1 2.8911 no . .
C9 H5 2.5428 no . .
C9 H8 2.9404 no . .
C9 H13 3.4380 no . .
C9 H15A 2.9921 no . .
C10 H5 2.5852 no . .
C10 H8 2.6275 no . .
C10 H12 2.6907 no . .
C10 H14B 3.4131 no . .
C10 H15A 2.8329 no . .
C11 H5 2.7984 no . .
C11 H6A 3.3174 no . .
C11 H7B 2.6802 no . .
C11 H12 2.8562 no . .
C12 H4 3.1855 no . .
C12 H5 3.0197 no . .
C12 H7B 2.7359 no . .
C12 H16 3.4754 no . .
C13 H5 3.1895 no . .
C13 H6A 2.7703 no . .
C13 H7B 3.3563 no . .
C13 H9 3.2514 no . .
C13 H11 3.2493 no . .
C13 H13 2.6702 no . .
C14 H6A 2.8626 no . .
C14 H10 3.2459 no . .
C14 H12 3.2440 no . .
C15 H11 3.2354 no . .
C16 H8 3.2446 no . .
C16 H12 3.2437 no . .
C17 H9 3.2348 no . .
C18 H5 3.2670 no . .
C18 H8 3.2438 no . .
C18 H10 3.2459 no . .
C18 H13 2.7785 no . .
C19 H4 2.9477 no . .
C19 H14B 3.2258 no . .
C19 H17 3.2375 no . .
C19 H18 3.2406 no . .
C20 H4 3.5724 no . .
C20 H14B 3.1271 no . .
C20 H19 3.2575 no . .
C21 H18 3.2415 no . .
C21 H20B 3.1119 no . .
C21 H21C 3.1483 no . .
C21 H22A 2.5579 no . .
C22 H16 3.2610 no . .
C22 H19 3.2582 no . .
C23 H4 3.5612 no . .
C23 H17 3.2414 no . .
C23 H20B 2.7796 no . .
C23 H21C 2.7420 no . .
C23 H22A 3.2983 no . .
C24 H4 2.9513 no . .
C24 H16 3.2583 no . .
C25 H17 2.6674 no . .
C25 H18 2.6662 no . .
H1 H2 2.3116 no . .
H2 H3 2.3152 no . .
H3 H4 2.3158 no . .
H4 H14B 3.4096 no . .
H4 H15A 2.8909 no . .
H4 H19 3.0847 no . .
H5 H6A 3.4553 no . .
H5 H7B 2.7438 no . .
H5 H12 2.8662 no . .
H5 H13 3.1483 no . .
H5 H15A 3.4660 no . .
H6A H8 2.4473 no . .
H7B H15A 2.3403 no . .
H8 H9 2.3204 no . .
H9 H10 2.3120 no . .
H10 H11 2.3142 no . .
H11 H12 2.3212 no . .
H12 H13 2.3981 no . .
H13 H14B 2.3299 no . .
H13 H15A 2.8603 no . .
H14B H16 2.6823 no . .
H16 H17 2.3191 no . .
H17 H20B 3.2870 no . .
H17 H21C 3.3383 no . .
H17 H22A 2.3520 no . .
H18 H19 2.3161 no . .
H18 H20B 2.7462 no . .
H18 H21C 2.6720 no . .
H18 H22A 3.5748 no . .
S1 H2 3.4499 no . 1_565
F1 H4 3.1920 no . 4_544
F1 H9 3.4903 no . 2_755
F1 H17 2.7761 no . 4_554
F1 H18 3.5618 no . 3_656
F1 H20B 3.0575 no . 3_656
F1 H21C 3.0552 no . 3_656
F2 H9 2.5429 no . 2_755
F2 H11 3.0196 no . 2_745
F2 H14B 3.1807 no . 4_544
F2 H15A 2.5457 no . 4_544
F3 H4 2.9320 no . 4_544
F3 H10 3.0297 no . 2_745
F3 H14B 3.0161 no . 4_544
F3 H15A 3.1258 no . 4_544
F3 H16 3.2196 no . 4_544
F3 H17 3.3937 no . 4_544
F3 H21C 3.2684 no . 3_656
O1 H10 2.6176 no . 2_745
O1 H11 2.7993 no . 2_745
O2 H6A 3.0975 no . 3_746
O2 H8 2.7276 no . 3_746
O2 H12 3.0529 no . 3_756
O2 H13 2.7840 no . 3_756
O3 H6A 3.0350 no . 1_565
O3 H7B 2.9334 no . 1_565
O4 H1 3.1568 no . 1_565
O4 H2 2.9610 no . 1_565
O4 H17 2.8450 no . 4_554
O4 H18 3.2008 no . 3_656
O4 H22A 3.0205 no . 4_554
C1 H18 3.3030 no . 3_656
C1 H21C 3.3475 no . 3_656
C2 H2 3.4982 no . 3_646
C2 H3 2.9810 no . 3_646
C2 H18 3.3235 no . 3_656
C2 H19 3.5108 no . 1_545
C3 H2 2.9806 no . 3_646
C3 H3 3.4579 no . 3_646
C3 H18 3.4251 no . 3_656
C3 H20B 3.4960 no . 2_646
C4 H18 3.4695 no . 3_656
C5 H18 3.4123 no . 3_656
C6 H18 3.3538 no . 3_656
C8 H4 3.5275 no . 4_544
C8 H9 3.5282 no . 2_755
C8 H15A 3.3570 no . 4_544
C9 H8 3.1783 no . 3_746
C9 H10 3.4697 no . 2_745
C9 H11 3.4943 no . 2_745
C10 H8 3.4283 no . 3_746
C10 H13 3.3194 no . 3_756
C11 H12 3.5387 no . 3_756
C11 H13 3.0528 no . 3_756
C13 H11 3.0773 no . 2_745
C13 H13 2.9961 no . 3_756
C14 H6A 3.4113 no . 3_746
C14 H11 2.8218 no . 2_745
C14 H13 3.5064 no . 3_756
C14 H14B 3.5881 no . 3_756
C15 H11 2.9864 no . 2_745
C15 H12 3.2584 no . 2_745
C15 H14B 3.2656 no . 3_756
C15 H16 2.7689 no . 3_756
C16 H11 3.3788 no . 2_745
C16 H12 3.3747 no . 2_745
C16 H14B 2.9687 no . 3_756
C16 H16 3.0599 no . 3_756
C17 H14B 3.0156 no . 3_756
C18 H11 3.4577 no . 2_745
C18 H13 3.1375 no . 3_756
C18 H14B 3.3709 no . 3_756
C19 H2 3.1087 no . 1_565
C19 H3 3.4847 no . 1_565
C20 H3 3.5273 no . 1_565
C20 H9 3.3274 no . 3_756
C21 H1 3.2372 no . 4_545
C21 H3 3.4917 no . 1_565
C22 H3 3.4200 no . 1_565
C22 H20B 3.4126 no . 2_656
C22 H21C 3.2743 no . 2_646
C23 H3 3.3555 no . 1_565
C23 H19 3.2539 no . 3_656
C23 H21C 3.4119 no . 2_646
C23 H22A 3.2514 no . 2_646
C24 H2 2.8877 no . 1_565
C24 H3 3.3969 no . 1_565
C24 H19 3.0233 no . 3_656
C25 H2 3.5239 no . 4_545
C25 H3 3.3847 no . 2_656
C25 H4 3.5136 no . 2_656
C25 H20B 3.2176 no . 2_656
C25 H21C 3.4135 no . 2_646
H1 O4 3.1568 no . 1_545
H1 C21 3.2372 no . 4_544
H1 H17 2.8752 no . 4_544
H1 H20B 3.5093 no . 4_544
H1 H21C 3.0646 no . 3_656
H1 H22A 3.2902 no . 4_544
H2 S1 3.4499 no . 1_545
H2 O4 2.9610 no . 1_545
H2 C2 3.4982 no . 3_646
H2 C3 2.9806 no . 3_646
H2 C19 3.1087 no . 1_545
H2 C24 2.8877 no . 1_545
H2 C25 3.5239 no . 4_544
H2 H2 3.3335 no . 3_646
H2 H3 2.3698 no . 3_646
H2 H19 2.7742 no . 1_545
H2 H20B 3.2247 no . 4_544
H2 H22A 2.9471 no . 4_544
H3 C2 2.9810 no . 3_646
H3 C3 3.4579 no . 3_646
H3 C19 3.4847 no . 1_545
H3 C20 3.5273 no . 1_545
H3 C21 3.4917 no . 1_545
H3 C22 3.4200 no . 1_545
H3 C23 3.3555 no . 1_545
H3 C24 3.3969 no . 1_545
H3 C25 3.3847 no . 2_646
H3 H2 2.3698 no . 3_646
H3 H3 3.2923 no . 3_646
H3 H20B 2.7319 no . 2_646
H3 H22A 3.2522 no . 2_646
H4 F1 3.1920 no . 4_545
H4 F3 2.9320 no . 4_545
H4 C8 3.5275 no . 4_545
H4 C25 3.5136 no . 2_646
H4 H20B 3.2626 no . 2_646
H4 H21C 3.2464 no . 2_646
H4 H22A 3.4553 no . 2_646
H6A O2 3.0975 no . 3_746
H6A O3 3.0350 no . 1_545
H6A C14 3.4113 no . 3_746
H6A H8 2.7330 no . 3_746
H6A H10 3.2049 no . 2_745
H6A H11 3.3660 no . 2_745
H7B O3 2.9334 no . 1_545
H7B H8 3.0005 no . 3_746
H8 O2 2.7276 no . 3_746
H8 C9 3.1783 no . 3_746
H8 C10 3.4283 no . 3_746
H8 H6A 2.7330 no . 3_746
H8 H7B 3.0005 no . 3_746
H8 H11 3.1265 no . 2_745
H9 F1 3.4903 no . 2_745
H9 F2 2.5429 no . 2_745
H9 C8 3.5282 no . 2_745
H9 C20 3.3274 no . 3_756
H9 H11 3.3660 no . 2_745
H9 H12 3.1659 no . 2_745
H9 H16 2.4575 no . 3_756
H10 F3 3.0297 no . 2_755
H10 O1 2.6176 no . 2_755
H10 C9 3.4697 no . 2_755
H10 H6A 3.2049 no . 2_755
H10 H12 3.3608 no . 2_745
H10 H14B 3.2891 no . 3_756
H10 H16 2.9829 no . 3_756
H10 H17 3.5811 no . 3_756
H11 F2 3.0196 no . 2_755
H11 O1 2.7993 no . 2_755
H11 C9 3.4943 no . 2_755
H11 C13 3.0773 no . 2_755
H11 C14 2.8218 no . 2_755
H11 C15 2.9864 no . 2_755
H11 C16 3.3788 no . 2_755
H11 C18 3.4577 no . 2_755
H11 H6A 3.3660 no . 2_755
H11 H8 3.1265 no . 2_755
H11 H9 3.3660 no . 2_755
H11 H14B 3.3492 no . 3_756
H12 O2 3.0529 no . 3_756
H12 C11 3.5387 no . 3_756
H12 C15 3.2584 no . 2_755
H12 C16 3.3747 no . 2_755
H12 H9 3.1659 no . 2_755
H12 H10 3.3608 no . 2_755
H12 H13 3.3280 no . 3_756
H13 O2 2.7840 no . 3_756
H13 C10 3.3194 no . 3_756
H13 C11 3.0528 no . 3_756
H13 C13 2.9961 no . 3_756
H13 C14 3.5064 no . 3_756
H13 C18 3.1375 no . 3_756
H13 H12 3.3280 no . 3_756
H13 H13 2.5350 no . 3_756
H14B F2 3.1807 no . 4_545
H14B F3 3.0161 no . 4_545
H14B C14 3.5881 no . 3_756
H14B C15 3.2656 no . 3_756
H14B C16 2.9687 no . 3_756
H14B C17 3.0156 no . 3_756
H14B C18 3.3709 no . 3_756
H14B H10 3.2891 no . 3_756
H14B H11 3.3492 no . 3_756
H15A F2 2.5457 no . 4_545
H15A F3 3.1258 no . 4_545
H15A C8 3.3570 no . 4_545
H16 F3 3.2196 no . 4_545
H16 C15 2.7689 no . 3_756
H16 C16 3.0599 no . 3_756
H16 H9 2.4575 no . 3_756
H16 H10 2.9829 no . 3_756
H17 F1 2.7761 no . 4_555
H17 F3 3.3937 no . 4_545
H17 O4 2.8450 no . 4_555
H17 H1 2.8752 no . 4_545
H17 H10 3.5811 no . 3_756
H18 F1 3.5618 no . 3_656
H18 O4 3.2008 no . 3_656
H18 C1 3.3030 no . 3_656
H18 C2 3.3235 no . 3_656
H18 C3 3.4251 no . 3_656
H18 C4 3.4695 no . 3_656
H18 C5 3.4123 no . 3_656
H18 C6 3.3538 no . 3_656
H18 H19 2.8202 no . 3_656
H18 H21C 3.5172 no . 2_646
H18 H22A 2.9782 no . 2_646
H19 C2 3.5108 no . 1_565
H19 C23 3.2539 no . 3_656
H19 C24 3.0233 no . 3_656
H19 H2 2.7742 no . 1_565
H19 H18 2.8202 no . 3_656
H19 H19 2.3622 no . 3_656
H19 H22A 3.4896 no . 4_554
H20B F1 3.0575 no . 3_656
H20B C3 3.4960 no . 2_656
H20B C22 3.4126 no . 2_646
H20B C25 3.2176 no . 2_646
H20B H1 3.5093 no . 4_545
H20B H2 3.2247 no . 4_545
H20B H3 2.7319 no . 2_656
H20B H4 3.2626 no . 2_656
H20B H21C 2.7517 no . 2_646
H20B H22A 3.1207 no . 2_646
H21C F1 3.0552 no . 3_656
H21C F3 3.2684 no . 3_656
H21C C1 3.3475 no . 3_656
H21C C22 3.2743 no . 2_656
H21C C23 3.4119 no . 2_656
H21C C25 3.4135 no . 2_656
H21C H1 3.0646 no . 3_656
H21C H4 3.2464 no . 2_656
H21C H18 3.5172 no . 2_656
H21C H20B 2.7517 no . 2_656
H22A O4 3.0205 no . 4_555
H22A C23 3.2514 no . 2_656
H22A H1 3.2902 no . 4_545
H22A H2 2.9471 no . 4_545
H22A H3 3.2522 no . 2_656
H22A H4 3.4553 no . 2_656
H22A H18 2.9782 no . 2_656
H22A H19 3.4896 no . 4_555
H22A H20B 3.1207 no . 2_656

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_170713Plakesh2
_database_code_depnum_ccdc_archive 'CCDC 1575065'
_audit_update_record             
;
2017-09-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H20 F3 N O4 S'
_chemical_formula_moiety         'C23 H20 F3 N O4 S'
_chemical_formula_weight         463.47
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.6966(3)
_cell_length_b                   9.11740(17)
_cell_length_c                   17.3812(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 116.0624(7)
_cell_angle_gamma                90.0000
_cell_volume                     2092.16(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16720
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.44
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960.00
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.979

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19472
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4771
_reflns_number_gt                4101
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1015
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4771
_refine_ls_number_parameters     289
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0523P)²+0.6593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.380
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.93559(3) 0.08665(4) 0.63631(2) 0.02800(10) Uani 1.0 4 d . . .
F1 F 0.95291(8) 0.30041(11) 0.86170(6) 0.0492(3) Uani 1.0 4 d . . .
F2 F 0.93819(9) 0.53225(13) 0.87476(6) 0.0524(3) Uani 1.0 4 d . . .
F3 F 1.07936(7) 0.44309(12) 0.88785(6) 0.0478(3) Uani 1.0 4 d . . .
O1 O 0.97023(8) 0.59280(11) 0.73506(7) 0.0321(3) Uani 1.0 4 d . . .
O2 O 1.21492(7) 0.55453(11) 0.65622(7) 0.0331(3) Uani 1.0 4 d . . .
O3 O 1.02408(8) 0.07245(12) 0.62196(7) 0.0375(3) Uani 1.0 4 d . . .
O4 O 0.94297(9) 0.06600(12) 0.72064(7) 0.0380(3) Uani 1.0 4 d . . .
N1 N 0.89444(9) 0.25280(13) 0.60647(7) 0.0268(3) Uani 1.0 4 d . . .
C1 C 0.81382(10) 0.31151(15) 0.62308(9) 0.0280(3) Uani 1.0 4 d . . .
C2 C 0.71352(11) 0.28104(18) 0.56689(10) 0.0360(4) Uani 1.0 4 d . . .
C3 C 0.63601(11) 0.34515(19) 0.58018(11) 0.0424(4) Uani 1.0 4 d . . .
C4 C 0.65795(12) 0.44151(19) 0.64756(12) 0.0416(4) Uani 1.0 4 d . . .
C5 C 0.75779(12) 0.47378(17) 0.70262(10) 0.0353(4) Uani 1.0 4 d . . .
C6 C 0.83743(10) 0.40721(15) 0.69208(9) 0.0281(3) Uani 1.0 4 d . . .
C7 C 0.94721(10) 0.44570(15) 0.74791(9) 0.0277(3) Uani 1.0 4 d . . .
C8 C 0.97869(12) 0.43196(17) 0.84320(10) 0.0349(4) Uani 1.0 4 d . . .
C9 C 0.95876(11) 0.61900(16) 0.64958(9) 0.0324(3) Uani 1.0 4 d . . .
C10 C 1.03919(10) 0.54273(15) 0.63229(8) 0.0273(3) Uani 1.0 4 d . . .
C11 C 1.02387(11) 0.41481(16) 0.59015(9) 0.0291(3) Uani 1.0 4 d . . .
C12 C 0.92443(11) 0.33391(16) 0.54691(9) 0.0307(3) Uani 1.0 4 d . . .
C13 C 1.13474(10) 0.62247(15) 0.66266(8) 0.0277(3) Uani 1.0 4 d . . .
C14 C 1.16066(12) 0.76298(17) 0.68946(9) 0.0350(3) Uani 1.0 4 d . . .
C15 C 1.26156(12) 0.78490(19) 0.69951(10) 0.0397(4) Uani 1.0 4 d . . .
C16 C 1.29053(11) 0.65722(18) 0.67925(10) 0.0380(4) Uani 1.0 4 d . . .
C17 C 0.84380(10) -0.03662(15) 0.56732(9) 0.0272(3) Uani 1.0 4 d . . .
C18 C 0.84068(11) -0.06883(16) 0.48792(9) 0.0310(3) Uani 1.0 4 d . . .
C19 C 0.76913(11) -0.16739(17) 0.43420(9) 0.0338(3) Uani 1.0 4 d . . .
C20 C 0.70029(11) -0.23464(16) 0.45825(10) 0.0321(3) Uani 1.0 4 d . . .
C21 C 0.62115(13) -0.33831(19) 0.39867(12) 0.0438(4) Uani 1.0 4 d . . .
C22 C 0.70545(11) -0.20138(17) 0.53836(10) 0.0349(4) Uani 1.0 4 d . . .
C23 C 0.77643(11) -0.10285(17) 0.59309(10) 0.0334(3) Uani 1.0 4 d . . .
H2 H 0.6983 0.2168 0.5198 0.0432 Uiso 1.0 4 calc R . .
H3 H 0.5675 0.3228 0.5428 0.0508 Uiso 1.0 4 calc R . .
H4 H 0.6045 0.4856 0.6561 0.0499 Uiso 1.0 4 calc R . .
H5 H 0.7723 0.5417 0.7480 0.0424 Uiso 1.0 4 calc R . .
H7 H 0.9906 0.3785 0.7328 0.0333 Uiso 1.0 4 calc R . .
H9A H 0.9622 0.7258 0.6410 0.0388 Uiso 1.0 4 calc R . .
H9B H 0.8912 0.5841 0.6079 0.0388 Uiso 1.0 4 calc R . .
H11 H 1.0810 0.3711 0.5873 0.0349 Uiso 1.0 4 calc R . .
H12A H 0.8705 0.4054 0.5142 0.0369 Uiso 1.0 4 calc R . .
H12B H 0.9290 0.2634 0.5054 0.0369 Uiso 1.0 4 calc R . .
H14 H 1.1195 0.8333 0.6996 0.0420 Uiso 1.0 4 calc R . .
H15 H 1.3003 0.8725 0.7170 0.0477 Uiso 1.0 4 calc R . .
H16 H 1.3550 0.6400 0.6806 0.0456 Uiso 1.0 4 calc R . .
H18 H 0.8871 -0.0238 0.4707 0.0372 Uiso 1.0 4 calc R . .
H19 H 0.7670 -0.1895 0.3800 0.0405 Uiso 1.0 4 calc R . .
H21A H 0.6289 -0.3486 0.3457 0.0525 Uiso 1.0 4 calc R . .
H21B H 0.6293 -0.4344 0.4262 0.0525 Uiso 1.0 4 calc R . .
H21C H 0.5536 -0.2995 0.3852 0.0525 Uiso 1.0 4 calc R . .
H22 H 0.6595 -0.2470 0.5559 0.0419 Uiso 1.0 4 calc R . .
H23 H 0.7790 -0.0809 0.6474 0.0401 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O3 1.4336(15) yes . .
S1 O4 1.4339(14) yes . .
S1 N1 1.6291(13) yes . .
S1 C17 1.7605(13) yes . .
F1 C8 1.339(2) yes . .
F2 C8 1.333(3) yes . .
F3 C8 1.3389(18) yes . .
O1 C7 1.4246(18) yes . .
O1 C9 1.440(2) yes . .
O2 C13 1.379(2) yes . .
O2 C16 1.3714(19) yes . .
N1 C1 1.440(3) yes . .
N1 C12 1.488(3) yes . .
C1 C2 1.3924(18) yes . .
C1 C6 1.398(2) yes . .
C2 C3 1.387(3) yes . .
C3 C4 1.384(3) yes . .
C4 C5 1.386(2) yes . .
C5 C6 1.400(3) yes . .
C6 C7 1.5140(18) yes . .
C7 C8 1.516(3) yes . .
C9 C10 1.511(3) yes . .
C10 C11 1.343(2) yes . .
C10 C13 1.459(2) yes . .
C11 C12 1.510(2) yes . .
C13 C14 1.359(2) yes . .
C14 C15 1.429(3) yes . .
C15 C16 1.339(3) yes . .
C17 C18 1.392(3) yes . .
C17 C23 1.391(3) yes . .
C18 C19 1.3865(19) yes . .
C19 C20 1.395(3) yes . .
C20 C21 1.503(2) yes . .
C20 C22 1.394(3) yes . .
C22 C23 1.389(2) yes . .
C2 H2 0.950 no . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C7 H7 1.000 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C11 H11 0.950 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C16 H16 0.950 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C21 H21A 0.980 no . .
C21 H21B 0.980 no . .
C21 H21C 0.980 no . .
C22 H22 0.950 no . .
C23 H23 0.950 no . .

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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O3 S1 O4 119.93(7) yes . . .
O3 S1 N1 105.48(8) yes . . .
O3 S1 C17 107.82(8) yes . . .
O4 S1 N1 107.36(7) yes . . .
O4 S1 C17 107.68(8) yes . . .
N1 S1 C17 108.10(6) yes . . .
C7 O1 C9 112.94(11) yes . . .
C13 O2 C16 106.34(12) yes . . .
S1 N1 C1 120.32(11) yes . . .
S1 N1 C12 120.11(12) yes . . .
C1 N1 C12 118.43(12) yes . . .
N1 C1 C2 119.73(14) yes . . .
N1 C1 C6 119.21(12) yes . . .
C2 C1 C6 120.90(16) yes . . .
C1 C2 C3 119.53(15) yes . . .
C2 C3 C4 120.36(14) yes . . .
C3 C4 C5 120.09(18) yes . . .
C4 C5 C6 120.65(16) yes . . .
C1 C6 C5 118.43(12) yes . . .
C1 C6 C7 119.18(15) yes . . .
C5 C6 C7 122.17(13) yes . . .
O1 C7 C6 112.17(11) yes . . .
O1 C7 C8 105.63(12) yes . . .
C6 C7 C8 114.13(15) yes . . .
F1 C8 F2 106.91(17) yes . . .
F1 C8 F3 106.61(12) yes . . .
F1 C8 C7 110.71(12) yes . . .
F2 C8 F3 106.79(12) yes . . .
F2 C8 C7 114.55(12) yes . . .
F3 C8 C7 110.85(16) yes . . .
O1 C9 C10 112.44(11) yes . . .
C9 C10 C11 123.36(14) yes . . .
C9 C10 C13 114.30(12) yes . . .
C11 C10 C13 122.30(15) yes . . .
C10 C11 C12 126.13(16) yes . . .
N1 C12 C11 114.48(12) yes . . .
O2 C13 C10 117.90(12) yes . . .
O2 C13 C14 109.30(14) yes . . .
C10 C13 C14 132.38(15) yes . . .
C13 C14 C15 107.05(16) yes . . .
C14 C15 C16 106.21(15) yes . . .
O2 C16 C15 111.09(16) yes . . .
S1 C17 C18 119.45(13) yes . . .
S1 C17 C23 119.91(13) yes . . .
C18 C17 C23 120.64(13) yes . . .
C17 C18 C19 119.30(17) yes . . .
C18 C19 C20 121.22(16) yes . . .
C19 C20 C21 120.89(17) yes . . .
C19 C20 C22 118.38(13) yes . . .
C21 C20 C22 120.72(17) yes . . .
C20 C22 C23 121.32(18) yes . . .
C17 C23 C22 119.14(17) yes . . .
C1 C2 H2 120.229 no . . .
C3 C2 H2 120.239 no . . .
C2 C3 H3 119.827 no . . .
C4 C3 H3 119.817 no . . .
C3 C4 H4 119.952 no . . .
C5 C4 H4 119.959 no . . .
C4 C5 H5 119.673 no . . .
C6 C5 H5 119.675 no . . .
O1 C7 H7 108.233 no . . .
C6 C7 H7 108.232 no . . .
C8 C7 H7 108.242 no . . .
O1 C9 H9A 109.116 no . . .
O1 C9 H9B 109.113 no . . .
C10 C9 H9A 109.108 no . . .
C10 C9 H9B 109.105 no . . .
H9A C9 H9B 107.850 no . . .
C10 C11 H11 116.932 no . . .
C12 C11 H11 116.939 no . . .
N1 C12 H12A 108.641 no . . .
N1 C12 H12B 108.641 no . . .
C11 C12 H12A 108.642 no . . .
C11 C12 H12B 108.646 no . . .
H12A C12 H12B 107.586 no . . .
C13 C14 H14 126.482 no . . .
C15 C14 H14 126.465 no . . .
C14 C15 H15 126.897 no . . .
C16 C15 H15 126.895 no . . .
O2 C16 H16 124.454 no . . .
C15 C16 H16 124.453 no . . .
C17 C18 H18 120.347 no . . .
C19 C18 H18 120.356 no . . .
C18 C19 H19 119.379 no . . .
C20 C19 H19 119.396 no . . .
C20 C21 H21A 109.466 no . . .
C20 C21 H21B 109.476 no . . .
C20 C21 H21C 109.474 no . . .
H21A C21 H21B 109.461 no . . .
H21A C21 H21C 109.482 no . . .
H21B C21 H21C 109.469 no . . .
C20 C22 H22 119.347 no . . .
C23 C22 H22 119.337 no . . .
C17 C23 H23 120.426 no . . .
C22 C23 H23 120.432 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 S1 N1 C1 -171.49(7) no . . . .
O3 S1 N1 C12 20.93(9) no . . . .
O3 S1 C17 C18 -31.77(11) no . . . .
O3 S1 C17 C23 147.06(9) no . . . .
O4 S1 N1 C1 -42.52(10) no . . . .
O4 S1 N1 C12 149.91(8) no . . . .
O4 S1 C17 C18 -162.51(9) no . . . .
O4 S1 C17 C23 16.32(12) no . . . .
N1 S1 C17 C18 81.80(11) no . . . .
N1 S1 C17 C23 -99.37(11) no . . . .
C17 S1 N1 C1 73.38(10) no . . . .
C17 S1 N1 C12 -94.19(10) no . . . .
C7 O1 C9 C10 -70.05(14) no . . . .
C9 O1 C7 C6 -63.64(16) no . . . .
C9 O1 C7 C8 171.45(11) no . . . .
C13 O2 C16 C15 -0.05(16) no . . . .
C16 O2 C13 C10 173.13(11) no . . . .
C16 O2 C13 C14 -0.36(14) no . . . .
S1 N1 C1 C2 -83.72(14) no . . . .
S1 N1 C1 C6 100.97(12) no . . . .
S1 N1 C12 C11 -86.01(13) no . . . .
C1 N1 C12 C11 106.18(13) no . . . .
C12 N1 C1 C2 84.06(15) no . . . .
C12 N1 C1 C6 -91.24(14) no . . . .
N1 C1 C2 C3 -176.01(12) no . . . .
N1 C1 C6 C5 174.20(12) no . . . .
N1 C1 C6 C7 -0.4(2) no . . . .
C2 C1 C6 C5 -1.0(3) no . . . .
C2 C1 C6 C7 -175.70(13) no . . . .
C6 C1 C2 C3 -0.8(3) no . . . .
C1 C2 C3 C4 1.5(3) no . . . .
C2 C3 C4 C5 -0.4(3) no . . . .
C3 C4 C5 C6 -1.4(3) no . . . .
C4 C5 C6 C1 2.2(3) no . . . .
C4 C5 C6 C7 176.65(15) no . . . .
C1 C6 C7 O1 108.43(15) no . . . .
C1 C6 C7 C8 -131.48(14) no . . . .
C5 C6 C7 O1 -66.0(2) no . . . .
C5 C6 C7 C8 54.08(18) no . . . .
O1 C7 C8 F1 175.09(12) no . . . .
O1 C7 C8 F2 54.12(17) no . . . .
O1 C7 C8 F3 -66.80(15) no . . . .
C6 C7 C8 F1 51.40(17) no . . . .
C6 C7 C8 F2 -69.57(16) no . . . .
C6 C7 C8 F3 169.51(11) no . . . .
O1 C9 C10 C11 99.28(13) no . . . .
O1 C9 C10 C13 -82.81(14) no . . . .
C9 C10 C11 C12 5.8(3) no . . . .
C9 C10 C13 O2 174.37(11) no . . . .
C9 C10 C13 C14 -14.0(2) no . . . .
C11 C10 C13 O2 -7.69(19) no . . . .
C11 C10 C13 C14 163.98(14) no . . . .
C13 C10 C11 C12 -171.93(12) no . . . .
C10 C11 C12 N1 -77.26(18) no . . . .
O2 C13 C14 C15 0.61(15) no . . . .
C10 C13 C14 C15 -171.60(14) no . . . .
C13 C14 C15 C16 -0.62(16) no . . . .
C14 C15 C16 O2 0.41(18) no . . . .
S1 C17 C18 C19 179.18(9) no . . . .
S1 C17 C23 C22 -179.10(9) no . . . .
C18 C17 C23 C22 -0.3(2) no . . . .
C23 C17 C18 C19 0.4(2) no . . . .
C17 C18 C19 C20 0.0(2) no . . . .
C18 C19 C20 C21 178.35(12) no . . . .
C18 C19 C20 C22 -0.5(2) no . . . .
C19 C20 C22 C23 0.6(2) no . . . .
C21 C20 C22 C23 -178.27(12) no . . . .
C20 C22 C23 C17 -0.2(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 C2 3.4334(16) no . .
S1 C6 3.5765(16) no . .
S1 C11 3.4919(17) no . .
F1 O1 3.5368(16) no . .
F1 O4 3.2071(17) no . .
F1 C5 3.3764(17) no . .
F1 C6 2.8502(16) no . .
F2 O1 2.7253(19) no . .
F2 C5 3.0488(16) no . .
F2 C6 3.0729(17) no . .
F3 O1 2.7831(14) no . .
O1 C1 3.4232(16) no . .
O1 C5 3.114(3) no . .
O1 C11 3.368(3) no . .
O1 C13 3.190(3) no . .
O1 C14 3.580(3) no . .
O2 C11 2.8270(18) no . .
O3 C11 3.1698(19) no . .
O3 C12 2.8019(18) no . .
O3 C18 2.9722(16) no . .
O4 C1 2.9429(17) no . .
O4 C6 3.4137(18) no . .
O4 C7 3.4910(18) no . .
O4 C23 2.9168(17) no . .
N1 C7 2.8395(19) no . .
N1 C9 3.4612(19) no . .
N1 C10 3.2978(19) no . .
N1 C18 3.4697(19) no . .
C1 C4 2.773(3) no . .
C1 C9 3.427(2) no . .
C1 C11 3.507(3) no . .
C1 C17 3.403(2) no . .
C2 C5 2.780(3) no . .
C2 C12 3.303(3) no . .
C2 C17 3.470(3) no . .
C2 C23 3.598(3) no . .
C3 C6 2.7940(18) no . .
C5 C8 3.112(2) no . .
C6 C9 2.935(3) no . .
C6 C12 3.359(3) no . .
C7 C10 3.006(3) no . .
C7 C11 3.403(3) no . .
C7 C12 3.511(3) no . .
C9 C12 3.067(2) no . .
C9 C14 3.033(3) no . .
C10 C16 3.571(3) no . .
C17 C20 2.7908(19) no . .
C18 C22 2.777(3) no . .
C19 C23 2.779(3) no . .
F1 C22 3.462(3) no . 2_656
F2 C3 3.270(3) no . 2_656
F3 C2 3.5151(18) no . 4_555
F3 C19 3.2612(19) no . 4_555
F3 C20 3.1322(18) no . 4_555
F3 C22 3.4005(18) no . 4_555
O1 C21 3.5319(19) no . 4_555
O2 C12 3.3676(17) no . 3_766
O2 C15 3.419(2) no . 2_746
O2 C21 3.553(3) no . 3_756
O3 C14 3.3612(19) no . 1_545
O3 C16 3.4186(17) no . 2_746
O3 C18 3.307(3) no . 3_756
O4 C4 3.424(3) no . 2_646
C2 F3 3.5151(18) no . 4_454
C3 F2 3.270(3) no . 2_646
C4 O4 3.424(3) no . 2_656
C9 C17 3.555(2) no . 1_565
C9 C23 3.502(3) no . 1_565
C10 C11 3.579(2) no . 3_766
C10 C12 3.566(3) no . 3_766
C11 C10 3.579(2) no . 3_766
C11 C11 3.285(3) no . 3_766
C12 O2 3.3676(17) no . 3_766
C12 C10 3.566(3) no . 3_766
C12 C13 3.376(2) no . 3_766
C13 C12 3.376(2) no . 3_766
C14 O3 3.3612(19) no . 1_565
C15 O2 3.419(2) no . 2_756
C16 O3 3.4186(17) no . 2_756
C17 C9 3.555(2) no . 1_545
C18 O3 3.307(3) no . 3_756
C19 F3 3.2612(19) no . 4_454
C20 F3 3.1322(18) no . 4_454
C21 O1 3.5319(19) no . 4_454
C21 O2 3.553(3) no . 3_756
C22 F1 3.462(3) no . 2_646
C22 F3 3.4005(18) no . 4_454
C23 C9 3.502(3) no . 1_545
S1 H2 3.3862 no . .
S1 H7 3.0581 no . .
S1 H12A 3.4758 no . .
S1 H12B 2.7549 no . .
S1 H18 2.8288 no . .
S1 H23 2.8395 no . .
F1 H5 3.3441 no . .
F1 H7 2.6320 no . .
F2 H5 2.4671 no . .
F2 H7 3.2129 no . .
F3 H7 2.4949 no . .
O1 H5 3.0496 no . .
O1 H14 3.3450 no . .
O2 H11 2.4568 no . .
O2 H14 3.1507 no . .
O2 H15 3.1514 no . .
O3 H7 3.5450 no . .
O3 H11 2.9867 no . .
O3 H12B 2.5694 no . .
O3 H18 2.6613 no . .
O4 H7 2.9191 no . .
O4 H23 2.5553 no . .
N1 H2 2.6214 no . .
N1 H7 2.3245 no . .
N1 H9B 3.0217 no . .
N1 H11 3.0974 no . .
N1 H18 3.4223 no . .
C1 H3 3.2596 no . .
C1 H5 3.2639 no . .
C1 H7 2.5312 no . .
C1 H9B 2.7939 no . .
C1 H12A 2.5285 no . .
C1 H12B 3.2062 no . .
C2 H4 3.2605 no . .
C2 H12A 3.0502 no . .
C2 H23 3.5487 no . .
C3 H5 3.2553 no . .
C4 H2 3.2617 no . .
C5 H3 3.2565 no . .
C5 H7 3.3414 no . .
C5 H9B 3.2258 no . .
C6 H2 3.2837 no . .
C6 H4 3.2769 no . .
C6 H9B 2.5269 no . .
C6 H12A 3.3340 no . .
C7 H5 2.7157 no . .
C7 H9A 3.2221 no . .
C7 H9B 2.5367 no . .
C8 H5 2.9205 no . .
C9 H7 2.5543 no . .
C9 H11 3.3492 no . .
C9 H12A 2.8860 no . .
C9 H14 2.8896 no . .
C10 H7 2.6263 no . .
C10 H12A 2.7303 no . .
C10 H12B 3.2916 no . .
C10 H14 2.9272 no . .
C11 H7 2.7490 no . .
C11 H9A 3.2172 no . .
C11 H9B 2.6093 no . .
C12 H2 3.3213 no . .
C12 H7 2.9640 no . .
C12 H9B 2.6498 no . .
C12 H18 3.4713 no . .
C13 H9A 2.5737 no . .
C13 H9B 3.2933 no . .
C13 H11 2.5854 no . .
C13 H15 3.1607 no . .
C13 H16 3.1163 no . .
C14 H9A 2.6786 no . .
C14 H16 3.1339 no . .
C16 H14 3.1311 no . .
C17 H2 3.0070 no . .
C17 H12B 3.3751 no . .
C17 H19 3.2540 no . .
C17 H22 3.2532 no . .
C18 H2 3.5335 no . .
C18 H12B 3.2566 no . .
C18 H23 3.2760 no . .
C19 H21A 2.5608 no . .
C19 H21B 3.1487 no . .
C19 H21C 3.1365 no . .
C19 H22 3.2541 no . .
C20 H18 3.2798 no . .
C20 H23 3.2821 no . .
C21 H19 2.6736 no . .
C21 H22 2.6687 no . .
C22 H19 3.2544 no . .
C22 H21A 3.3118 no . .
C22 H21B 2.7652 no . .
C22 H21C 2.7652 no . .
C23 H2 3.1859 no . .
C23 H18 3.2753 no . .
H2 H3 2.3381 no . .
H2 H12A 3.0964 no . .
H2 H12B 3.5326 no . .
H2 H23 3.3743 no . .
H3 H4 2.3308 no . .
H4 H5 2.3311 no . .
H5 H9B 3.5872 no . .
H7 H9A 3.4875 no . .
H7 H9B 2.7528 no . .
H7 H11 3.3337 no . .
H7 H12A 3.4227 no . .
H9A H12A 3.5496 no . .
H9A H14 2.2965 no . .
H9B H11 3.5438 no . .
H9B H12A 2.2279 no . .
H9B H12B 3.5916 no . .
H11 H12A 2.7975 no . .
H11 H12B 2.2774 no . .
H12B H18 2.6965 no . .
H14 H15 2.5639 no . .
H15 H16 2.4466 no . .
H18 H19 2.3327 no . .
H19 H21A 2.3482 no . .
H19 H21B 3.3386 no . .
H19 H21C 3.3305 no . .
H21A H22 3.5995 no . .
H21B H22 2.7042 no . .
H21C H22 2.7189 no . .
H22 H23 2.3353 no . .
S1 H9A 3.3095 no . 1_545
S1 H14 3.3519 no . 1_545
S1 H16 3.3507 no . 2_746
F1 H2 3.4456 no . 4_555
F1 H3 3.0580 no . 4_555
F1 H4 2.9693 no . 2_646
F1 H16 3.5323 no . 2_746
F1 H22 2.6550 no . 2_656
F1 H23 3.5116 no . 2_656
F2 H3 3.0299 no . 2_656
F2 H21C 2.9290 no . 4_555
F2 H22 3.3942 no . 2_656
F2 H23 3.2119 no . 2_656
F3 H2 2.6299 no . 4_555
F3 H15 3.1144 no . 2_746
F3 H16 3.3157 no . 2_746
F3 H21C 3.2697 no . 4_555
O1 H21A 3.2613 no . 4_555
O1 H21C 3.0092 no . 4_555
O2 H12A 2.6864 no . 3_766
O2 H12B 3.1461 no . 3_766
O2 H14 3.3033 no . 2_746
O2 H15 2.8442 no . 2_746
O2 H19 3.4191 no . 3_756
O2 H21A 2.9771 no . 3_756
O2 H21B 3.3725 no . 3_756
O3 H9A 3.3451 no . 1_545
O3 H14 2.6223 no . 1_545
O3 H16 3.1545 no . 2_746
O3 H18 2.5189 no . 3_756
O3 H19 3.2656 no . 3_756
O4 H4 2.6324 no . 2_646
O4 H5 3.4460 no . 2_646
O4 H9A 3.4577 no . 1_545
O4 H14 3.4924 no . 1_545
O4 H16 2.7819 no . 2_746
O4 H21A 3.3017 no . 4_545
O4 H21C 3.5555 no . 4_545
C2 H21B 3.4033 no . 1_565
C3 H21B 3.3137 no . 1_565
C3 H21C 3.1266 no . 3_656
C4 H21C 3.1801 no . 3_656
C4 H22 3.2613 no . 1_565
C4 H23 3.2704 no . 2_656
C5 H22 3.4402 no . 1_565
C5 H23 2.9274 no . 2_656
C7 H15 3.5495 no . 2_746
C8 H21C 3.5029 no . 4_555
C10 H11 3.5180 no . 3_766
C10 H12A 3.3820 no . 3_766
C10 H12B 3.1710 no . 3_766
C10 H15 3.0664 no . 2_746
C11 H11 3.3938 no . 3_766
C11 H12A 3.2955 no . 3_766
C11 H12B 3.5857 no . 3_766
C11 H15 3.2321 no . 2_746
C11 H19 3.5409 no . 3_756
C12 H11 3.5378 no . 3_766
C13 H12A 3.0517 no . 3_766
C13 H12B 2.8441 no . 3_766
C13 H15 2.9535 no . 2_746
C13 H19 3.4597 no . 4_555
C14 H12B 3.0568 no . 3_766
C14 H18 3.4900 no . 3_766
C14 H19 3.0514 no . 4_555
C14 H21A 3.0528 no . 4_555
C15 H7 3.4072 no . 2_756
C15 H11 3.4889 no . 2_756
C15 H12B 3.4577 no . 3_766
C15 H18 3.5482 no . 3_766
C15 H19 3.2227 no . 4_555
C16 H7 3.5255 no . 2_756
C16 H12A 3.2002 no . 3_766
C16 H12B 3.4831 no . 3_766
C16 H14 3.5294 no . 2_746
C16 H21A 3.1558 no . 3_756
C16 H21B 3.2822 no . 3_756
C17 H9A 2.7203 no . 1_545
C17 H9B 3.5363 no . 1_545
C18 H9A 3.0983 no . 1_545
C18 H11 3.4570 no . 3_756
C19 H9A 3.5997 no . 1_545
C19 H9B 3.5642 no . 1_545
C19 H11 3.0272 no . 3_756
C19 H15 3.5810 no . 3_766
C20 H9B 3.3095 no . 1_545
C21 H3 3.3490 no . 3_656
C21 H4 3.3067 no . 3_656
C21 H14 3.4498 no . 4_454
C21 H16 3.1646 no . 3_756
C22 H9A 3.4559 no . 1_545
C22 H9B 3.1364 no . 1_545
C23 H5 3.4093 no . 2_646
C23 H9A 2.9303 no . 1_545
C23 H9B 3.2671 no . 1_545
H2 F1 3.4456 no . 4_454
H2 F3 2.6299 no . 4_454
H2 H16 3.4723 no . 3_766
H2 H21B 3.5125 no . 1_565
H3 F1 3.0580 no . 4_454
H3 F2 3.0299 no . 2_646
H3 C21 3.3490 no . 3_656
H3 H21B 3.3846 no . 1_565
H3 H21B 3.3255 no . 3_656
H3 H21C 2.5949 no . 3_656
H3 H22 3.0853 no . 3_656
H4 F1 2.9693 no . 2_656
H4 O4 2.6324 no . 2_656
H4 C21 3.3067 no . 3_656
H4 H21B 3.1236 no . 3_656
H4 H21C 2.7072 no . 3_656
H4 H22 3.2964 no . 1_565
H4 H23 3.1346 no . 2_656
H5 O4 3.4460 no . 2_656
H5 C23 3.4093 no . 2_656
H5 H22 3.5695 no . 1_565
H5 H23 2.5157 no . 2_656
H7 C15 3.4072 no . 2_746
H7 C16 3.5255 no . 2_746
H7 H15 2.8015 no . 2_746
H7 H16 3.0229 no . 2_746
H9A S1 3.3095 no . 1_565
H9A O3 3.3451 no . 1_565
H9A O4 3.4577 no . 1_565
H9A C17 2.7203 no . 1_565
H9A C18 3.0983 no . 1_565
H9A C19 3.5997 no . 1_565
H9A C22 3.4559 no . 1_565
H9A C23 2.9303 no . 1_565
H9A H12B 3.5534 no . 3_766
H9A H18 3.5103 no . 1_565
H9A H21A 3.5008 no . 4_555
H9A H23 3.2603 no . 1_565
H9B C17 3.5363 no . 1_565
H9B C19 3.5642 no . 1_565
H9B C20 3.3095 no . 1_565
H9B C22 3.1364 no . 1_565
H9B C23 3.2671 no . 1_565
H9B H22 3.4751 no . 1_565
H11 C10 3.5180 no . 3_766
H11 C11 3.3938 no . 3_766
H11 C12 3.5378 no . 3_766
H11 C15 3.4889 no . 2_746
H11 C18 3.4570 no . 3_756
H11 C19 3.0272 no . 3_756
H11 H12A 2.9793 no . 3_766
H11 H15 3.0657 no . 2_746
H11 H18 3.4178 no . 3_756
H11 H19 2.6349 no . 3_756
H12A O2 2.6864 no . 3_766
H12A C10 3.3820 no . 3_766
H12A C11 3.2955 no . 3_766
H12A C13 3.0517 no . 3_766
H12A C16 3.2002 no . 3_766
H12A H11 2.9793 no . 3_766
H12A H16 3.5725 no . 3_766
H12A H21B 3.5031 no . 1_565
H12B O2 3.1461 no . 3_766
H12B C10 3.1710 no . 3_766
H12B C11 3.5857 no . 3_766
H12B C13 2.8441 no . 3_766
H12B C14 3.0568 no . 3_766
H12B C15 3.4577 no . 3_766
H12B C16 3.4831 no . 3_766
H12B H9A 3.5534 no . 3_766
H12B H14 3.4280 no . 3_766
H12B H18 3.3573 no . 3_756
H14 S1 3.3519 no . 1_565
H14 O2 3.3033 no . 2_756
H14 O3 2.6223 no . 1_565
H14 O4 3.4924 no . 1_565
H14 C16 3.5294 no . 2_756
H14 C21 3.4498 no . 4_555
H14 H12B 3.4280 no . 3_766
H14 H16 3.4066 no . 2_756
H14 H18 3.3963 no . 3_766
H14 H19 3.2059 no . 4_555
H14 H21A 2.4863 no . 4_555
H15 F3 3.1144 no . 2_756
H15 O2 2.8442 no . 2_756
H15 C7 3.5495 no . 2_756
H15 C10 3.0664 no . 2_756
H15 C11 3.2321 no . 2_756
H15 C13 2.9535 no . 2_756
H15 C19 3.5810 no . 3_766
H15 H7 2.8015 no . 2_756
H15 H11 3.0657 no . 2_756
H15 H18 3.4985 no . 3_766
H15 H19 3.2729 no . 3_766
H15 H19 3.5022 no . 4_555
H16 S1 3.3507 no . 2_756
H16 F1 3.5323 no . 2_756
H16 F3 3.3157 no . 2_756
H16 O3 3.1545 no . 2_756
H16 O4 2.7819 no . 2_756
H16 C21 3.1646 no . 3_756
H16 H2 3.4723 no . 3_766
H16 H7 3.0229 no . 2_756
H16 H12A 3.5725 no . 3_766
H16 H14 3.4066 no . 2_746
H16 H21A 2.7240 no . 3_756
H16 H21B 2.7194 no . 3_756
H18 O3 2.5189 no . 3_756
H18 C14 3.4900 no . 3_766
H18 C15 3.5482 no . 3_766
H18 H9A 3.5103 no . 1_545
H18 H11 3.4178 no . 3_756
H18 H12B 3.3573 no . 3_756
H18 H14 3.3963 no . 3_766
H18 H15 3.4985 no . 3_766
H18 H18 3.0449 no . 3_756
H19 O2 3.4191 no . 3_756
H19 O3 3.2656 no . 3_756
H19 C11 3.5409 no . 3_756
H19 C13 3.4597 no . 4_454
H19 C14 3.0514 no . 4_454
H19 C15 3.2227 no . 4_454
H19 H11 2.6349 no . 3_756
H19 H14 3.2059 no . 4_454
H19 H15 3.2729 no . 3_766
H19 H15 3.5022 no . 4_454
H21A O1 3.2613 no . 4_454
H21A O2 2.9771 no . 3_756
H21A O4 3.3017 no . 4_444
H21A C14 3.0528 no . 4_454
H21A C16 3.1558 no . 3_756
H21A H9A 3.5008 no . 4_454
H21A H14 2.4863 no . 4_454
H21A H16 2.7240 no . 3_756
H21B O2 3.3725 no . 3_756
H21B C2 3.4033 no . 1_545
H21B C3 3.3137 no . 1_545
H21B C16 3.2822 no . 3_756
H21B H2 3.5125 no . 1_545
H21B H3 3.3846 no . 1_545
H21B H3 3.3255 no . 3_656
H21B H4 3.1236 no . 3_656
H21B H12A 3.5031 no . 1_545
H21B H16 2.7194 no . 3_756
H21C F2 2.9290 no . 4_454
H21C F3 3.2697 no . 4_454
H21C O1 3.0092 no . 4_454
H21C O4 3.5555 no . 4_444
H21C C3 3.1266 no . 3_656
H21C C4 3.1801 no . 3_656
H21C C8 3.5029 no . 4_454
H21C H3 2.5949 no . 3_656
H21C H4 2.7072 no . 3_656
H22 F1 2.6550 no . 2_646
H22 F2 3.3942 no . 2_646
H22 C4 3.2613 no . 1_545
H22 C5 3.4402 no . 1_545
H22 H3 3.0853 no . 3_656
H22 H4 3.2964 no . 1_545
H22 H5 3.5695 no . 1_545
H22 H9B 3.4751 no . 1_545
H23 F1 3.5116 no . 2_646
H23 F2 3.2119 no . 2_646
H23 C4 3.2704 no . 2_646
H23 C5 2.9274 no . 2_646
H23 H4 3.1346 no . 2_646
H23 H5 2.5157 no . 2_646
H23 H9A 3.2603 no . 1_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
