# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_dm16677
_database_code_depnum_ccdc_archive 'CCDC 1527560'
_audit_update_record             
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H16 F3 N O2 S2'
_chemical_formula_sum            'C11 H16 F3 N O2 S2'
_chemical_formula_weight         315.37
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   11.500(4)
_cell_length_b                   10.460(4)
_cell_length_c                   11.413(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.060(8)
_cell_angle_gamma                90
_cell_volume                     1367.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3895
_cell_measurement_temperature    130
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0774 before and 0.0372 after correction.
The Ratio of minimum to maximum transmission is 0.8406.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5043
_diffrn_reflns_point_group_measured_fraction_full 0.783
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.200
_diffrn_reflns_theta_min         1.791
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.481
_reflns_Friedel_fraction_full    0.542
_reflns_Friedel_fraction_max     0.533
_reflns_number_gt                2219
_reflns_number_total             2368
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+2.8276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.048
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.07841(9) -0.50966(10) -0.65191(8) 0.0240(2) Uani 1 1 d . . . . .
S2 S -0.22285(8) -0.69682(11) -0.55800(7) 0.0210(2) Uani 1 1 d . . . . .
F1 F -0.1196(3) -0.2970(3) -0.7524(3) 0.0534(9) Uani 1 1 d . . . . .
F2 F -0.2780(3) -0.3976(4) -0.7225(3) 0.0495(9) Uani 1 1 d . . . . .
F3 F -0.1787(4) -0.4546(4) -0.8619(2) 0.0567(10) Uani 1 1 d . . . . .
O1 O -0.1511(3) -0.6782(4) -0.4499(2) 0.0322(8) Uani 1 1 d . . . . .
O2 O -0.3346(3) -0.6355(4) -0.5684(3) 0.0339(8) Uani 1 1 d . . . . .
N1 N -0.1488(3) -0.6509(4) -0.6734(3) 0.0205(7) Uani 1 1 d . . . . .
C1 C -0.1703(4) -0.4126(5) -0.7519(4) 0.0303(10) Uani 1 1 d . . . . .
C2 C -0.2293(4) -0.8629(5) -0.5955(3) 0.0272(9) Uani 1 1 d . . . . .
H2A H -0.1917 -0.9150 -0.5304 0.033 Uiso 1 1 calc R . . . .
H2B H -0.3115 -0.8909 -0.6111 0.033 Uiso 1 1 calc R . . . .
C3 C -0.0843(3) -0.7616(4) -0.7188(3) 0.0208(8) Uani 1 1 d . . . . .
H3 H -0.0077 -0.7738 -0.6715 0.025 Uiso 1 1 calc R . . . .
C4 C -0.0675(4) -0.7576(5) -0.8521(4) 0.0260(9) Uani 1 1 d . . . . .
H4A H -0.1069 -0.6826 -0.8907 0.031 Uiso 1 1 calc R . . . .
H4B H 0.0163 -0.7560 -0.8661 0.031 Uiso 1 1 calc R . . . .
C5 C -0.1260(4) -0.8839(5) -0.8957(3) 0.0254(9) Uani 1 1 d . . . . .
H5 H -0.1419 -0.8894 -0.9832 0.030 Uiso 1 1 calc R . . . .
C6 C -0.0544(4) -0.9953(5) -0.8412(4) 0.0306(10) Uani 1 1 d . . . . .
H6A H 0.0301 -0.9817 -0.8473 0.037 Uiso 1 1 calc R . . . .
H6B H -0.0781 -1.0770 -0.8801 0.037 Uiso 1 1 calc R . . . .
C7 C -0.0833(4) -0.9948(5) -0.7093(4) 0.0275(9) Uani 1 1 d . . . . .
H7A H -0.1236 -1.0744 -0.6890 0.033 Uiso 1 1 calc R . . . .
H7B H -0.0120 -0.9839 -0.6551 0.033 Uiso 1 1 calc R . . . .
C8 C -0.1640(3) -0.8785(4) -0.7065(3) 0.0192(8) Uani 1 1 d . . . . .
C9 C -0.2372(4) -0.8872(4) -0.8284(3) 0.0224(9) Uani 1 1 d . . . . .
C10 C -0.3065(4) -1.0136(6) -0.8436(4) 0.0347(11) Uani 1 1 d . . . . .
H10A H -0.3496 -1.0154 -0.9216 0.052 Uiso 1 1 calc GR . . . .
H10B H -0.3615 -1.0196 -0.7830 0.052 Uiso 1 1 calc GR . . . .
H10C H -0.2522 -1.0860 -0.8360 0.052 Uiso 1 1 calc GR . . . .
C11 C -0.3227(4) -0.7776(6) -0.8579(4) 0.0317(10) Uani 1 1 d . . . . .
H11A H -0.3835 -0.7785 -0.8029 0.048 Uiso 1 1 calc GR . . . .
H11B H -0.3587 -0.7880 -0.9384 0.048 Uiso 1 1 calc GR . . . .
H11C H -0.2807 -0.6960 -0.8512 0.048 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.692(4) . ?
S1 C1 1.799(5) . ?
S2 O1 1.436(3) . ?
S2 O2 1.432(3) . ?
S2 N1 1.700(3) . ?
S2 C2 1.790(5) . ?
F1 C1 1.342(6) . ?
F2 C1 1.321(6) . ?
F3 C1 1.325(6) . ?
N1 C3 1.492(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C8 1.537(5) . ?
C3 H3 1.0000 . ?
C3 C4 1.552(5) . ?
C3 C8 1.542(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.545(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.527(7) . ?
C5 C9 1.550(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.570(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.533(6) . ?
C8 C9 1.564(5) . ?
C9 C10 1.545(7) . ?
C9 C11 1.528(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C1 98.9(2) . . ?
O1 S2 N1 109.78(18) . . ?
O1 S2 C2 110.3(2) . . ?
O2 S2 O1 117.0(2) . . ?
O2 S2 N1 108.46(19) . . ?
O2 S2 C2 113.4(2) . . ?
N1 S2 C2 95.86(18) . . ?
S1 N1 S2 113.62(19) . . ?
C3 N1 S1 118.8(3) . . ?
C3 N1 S2 110.4(3) . . ?
F1 C1 S1 106.3(4) . . ?
F2 C1 S1 114.7(3) . . ?
F2 C1 F1 108.2(4) . . ?
F2 C1 F3 106.7(4) . . ?
F3 C1 S1 113.8(3) . . ?
F3 C1 F1 106.9(4) . . ?
S2 C2 H2A 110.4 . . ?
S2 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C8 C2 S2 106.7(3) . . ?
C8 C2 H2A 110.4 . . ?
C8 C2 H2B 110.4 . . ?
N1 C3 H3 110.7 . . ?
N1 C3 C4 115.4(4) . . ?
N1 C3 C8 105.4(3) . . ?
C4 C3 H3 110.7 . . ?
C8 C3 H3 110.7 . . ?
C8 C3 C4 103.7(3) . . ?
C3 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
C5 C4 C3 101.8(3) . . ?
C5 C4 H4A 111.4 . . ?
C5 C4 H4B 111.4 . . ?
C4 C5 H5 114.0 . . ?
C4 C5 C9 102.4(3) . . ?
C6 C5 C4 108.5(4) . . ?
C6 C5 H5 114.0 . . ?
C6 C5 C9 102.7(3) . . ?
C9 C5 H5 114.0 . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
C5 C6 C7 103.7(3) . . ?
H6A C6 H6B 109.0 . . ?
C7 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C6 C7 H7A 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
C8 C7 C6 101.7(4) . . ?
C8 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
C2 C8 C3 109.2(3) . . ?
C2 C8 C9 118.4(3) . . ?
C3 C8 C9 104.1(3) . . ?
C7 C8 C2 116.2(4) . . ?
C7 C8 C3 105.2(3) . . ?
C7 C8 C9 102.4(3) . . ?
C5 C9 C8 92.1(3) . . ?
C10 C9 C5 113.8(4) . . ?
C10 C9 C8 112.4(4) . . ?
C11 C9 C5 114.7(4) . . ?
C11 C9 C8 115.9(4) . . ?
C11 C9 C10 107.6(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C3 C4 -76.3(4) . . . . ?
S1 N1 C3 C8 169.9(2) . . . . ?
S2 N1 C3 C4 149.9(3) . . . . ?
S2 N1 C3 C8 36.2(4) . . . . ?
S2 C2 C8 C3 19.1(4) . . . . ?
S2 C2 C8 C7 137.8(3) . . . . ?
S2 C2 C8 C9 -99.6(4) . . . . ?
O1 S2 N1 S1 -45.0(3) . . . . ?
O1 S2 N1 C3 91.3(3) . . . . ?
O1 S2 C2 C8 -112.1(3) . . . . ?
O2 S2 N1 S1 84.0(3) . . . . ?
O2 S2 N1 C3 -139.7(3) . . . . ?
O2 S2 C2 C8 114.5(3) . . . . ?
N1 S1 C1 F1 -175.0(3) . . . . ?
N1 S1 C1 F2 65.6(4) . . . . ?
N1 S1 C1 F3 -57.7(4) . . . . ?
N1 S2 C2 C8 1.5(3) . . . . ?
N1 C3 C4 C5 -122.2(4) . . . . ?
N1 C3 C8 C2 -34.6(4) . . . . ?
N1 C3 C8 C7 -160.0(3) . . . . ?
N1 C3 C8 C9 92.7(4) . . . . ?
C1 S1 N1 S2 -108.2(2) . . . . ?
C1 S1 N1 C3 119.4(3) . . . . ?
C2 S2 N1 S1 -159.0(2) . . . . ?
C2 S2 N1 C3 -22.7(3) . . . . ?
C2 C8 C9 C5 173.5(4) . . . . ?
C2 C8 C9 C10 -69.7(5) . . . . ?
C2 C8 C9 C11 54.7(5) . . . . ?
C3 C4 C5 C6 -66.1(4) . . . . ?
C3 C4 C5 C9 42.0(4) . . . . ?
C3 C8 C9 C5 52.1(4) . . . . ?
C3 C8 C9 C10 169.0(3) . . . . ?
C3 C8 C9 C11 -66.7(4) . . . . ?
C4 C3 C8 C2 -156.3(4) . . . . ?
C4 C3 C8 C7 78.4(4) . . . . ?
C4 C3 C8 C9 -28.9(4) . . . . ?
C4 C5 C6 C7 73.4(4) . . . . ?
C4 C5 C9 C8 -57.2(4) . . . . ?
C4 C5 C9 C10 -172.8(4) . . . . ?
C4 C5 C9 C11 62.7(4) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C6 C5 C9 C8 55.3(4) . . . . ?
C6 C5 C9 C10 -60.3(4) . . . . ?
C6 C5 C9 C11 175.2(4) . . . . ?
C6 C7 C8 C2 168.6(4) . . . . ?
C6 C7 C8 C3 -70.5(4) . . . . ?
C6 C7 C8 C9 38.0(4) . . . . ?
C7 C8 C9 C5 -57.2(4) . . . . ?
C7 C8 C9 C10 59.6(4) . . . . ?
C7 C8 C9 C11 -176.0(4) . . . . ?
C8 C3 C4 C5 -7.5(4) . . . . ?
C9 C5 C6 C7 -34.5(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_dm16671_0m
_database_code_depnum_ccdc_archive 'CCDC 1527559'
_audit_update_record             
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H10 F4 O2 S'
_chemical_formula_sum            'C19 H10 F4 O2 S'
_chemical_formula_weight         378.33
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.6977(5)
_cell_length_b                   8.1914(6)
_cell_length_c                   30.513(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1674.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.639
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0524 before and 0.0394 after correction.
The Ratio of minimum to maximum transmission is 0.8228.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            17063
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.677
_diffrn_reflns_theta_min         2.575
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4931
_reflns_number_total             5168
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.3678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0875
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C13(H13), C14(H14), C16(H16),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.08576(7) 0.24905(6) 0.61490(2) 0.02434(10) Uani 1 1 d . . . . .
F1 F 0.0320(3) 0.2658(2) 0.70075(4) 0.0533(4) Uani 1 1 d . . . . .
F2 F 0.2669(2) 0.1052(2) 0.68098(5) 0.0481(4) Uani 1 1 d . . . . .
F3 F -0.0411(2) 0.0384(2) 0.66985(5) 0.0507(4) Uani 1 1 d . . . . .
F4 F 0.2887(2) 0.89826(15) 0.39813(4) 0.0293(3) Uani 1 1 d . . . . .
O1 O 0.5596(3) 0.16263(19) 0.59978(5) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.6126(2) 0.33579(17) 0.65540(4) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.3097(2) 0.37889(18) 0.61536(5) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.5037(3) 0.2758(2) 0.62103(5) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.3252(3) 0.4927(2) 0.65379(5) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.5050(3) 0.4630(2) 0.67459(6) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.5706(5) 0.5475(3) 0.71092(8) 0.0427(6) Uani 1 1 d . . . . .
H5 H 0.6960 0.5254 0.7242 0.051 Uiso 1 1 calc R . . . .
C6 C 0.4435(6) 0.6660(3) 0.72690(8) 0.0552(9) Uani 1 1 d . . . . .
H6 H 0.4825 0.7280 0.7518 0.066 Uiso 1 1 calc R . . . .
C7 C 0.2582(5) 0.6969(3) 0.70724(7) 0.0469(7) Uani 1 1 d . . . . .
H7 H 0.1728 0.7778 0.7194 0.056 Uiso 1 1 calc R . . . .
C8 C 0.1974(4) 0.6113(2) 0.67033(6) 0.0307(4) Uani 1 1 d . . . . .
H8 H 0.0725 0.6330 0.6568 0.037 Uiso 1 1 calc R . . . .
C9 C 0.0875(4) 0.1620(3) 0.66926(7) 0.0344(5) Uani 1 1 d . . . . .
C10 C 0.3102(3) 0.45798(19) 0.56976(5) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.3113(2) 0.62502(19) 0.56455(5) 0.0160(3) Uani 1 1 d . . . . .
H11 H 0.3133 0.6936 0.5896 0.019 Uiso 1 1 calc R . . . .
C12 C 0.3094(2) 0.69604(19) 0.52190(5) 0.0154(3) Uani 1 1 d . . . . .
C13 C 0.3097(3) 0.8679(2) 0.51598(6) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.3137 0.9378 0.5408 0.024 Uiso 1 1 calc R . . . .
C14 C 0.3042(3) 0.9339(2) 0.47464(6) 0.0215(3) Uani 1 1 d . . . . .
H14 H 0.3042 1.0488 0.4706 0.026 Uiso 1 1 calc R . . . .
C15 C 0.2985(3) 0.8283(2) 0.43859(6) 0.0206(3) Uani 1 1 d . . . . .
C16 C 0.2997(3) 0.6621(2) 0.44169(6) 0.0194(3) Uani 1 1 d . . . . .
H16 H 0.2969 0.5952 0.4163 0.023 Uiso 1 1 calc R . . . .
C17 C 0.3052(3) 0.5926(2) 0.48453(5) 0.0169(3) Uani 1 1 d . . . . .
C18 C 0.3064(3) 0.4204(2) 0.49078(5) 0.0200(3) Uani 1 1 d . . . . .
H18 H 0.3054 0.3501 0.4660 0.024 Uiso 1 1 calc R . . . .
C19 C 0.3091(3) 0.3549(2) 0.53207(5) 0.0203(3) Uani 1 1 d . . . . .
H19 H 0.3102 0.2397 0.5356 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.8386(17) . ?
S1 C9 1.805(2) . ?
F1 C9 1.336(3) . ?
F2 C9 1.337(3) . ?
F3 C9 1.330(3) . ?
F4 C15 1.3626(19) . ?
O1 C2 1.192(2) . ?
O2 C2 1.369(2) . ?
O2 C4 1.396(2) . ?
C1 C2 1.559(2) . ?
C1 C3 1.501(2) . ?
C1 C10 1.535(2) . ?
C3 C4 1.383(3) . ?
C3 C8 1.389(3) . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.378(2) . ?
C10 C19 1.427(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.425(2) . ?
C12 C13 1.419(2) . ?
C12 C17 1.421(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(3) . ?
C15 C16 1.364(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.426(2) . ?
C17 C18 1.423(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.369(2) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C1 102.48(9) . . ?
C2 O2 C4 108.30(14) . . ?
C2 C1 S1 111.55(11) . . ?
C3 C1 S1 114.92(12) . . ?
C3 C1 C2 101.07(14) . . ?
C3 C1 C10 116.47(13) . . ?
C10 C1 S1 103.84(11) . . ?
C10 C1 C2 109.10(13) . . ?
O1 C2 O2 121.90(17) . . ?
O1 C2 C1 128.54(17) . . ?
O2 C2 C1 109.56(14) . . ?
C4 C3 C1 108.02(15) . . ?
C4 C3 C8 119.50(17) . . ?
C8 C3 C1 132.47(18) . . ?
C3 C4 O2 112.87(16) . . ?
C5 C4 O2 123.2(2) . . ?
C5 C4 C3 123.9(2) . . ?
C4 C5 H5 121.9 . . ?
C4 C5 C6 116.2(2) . . ?
C6 C5 H5 121.9 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 H8 121.1 . . ?
C7 C8 C3 117.9(2) . . ?
C7 C8 H8 121.1 . . ?
F1 C9 S1 114.07(16) . . ?
F1 C9 F2 106.2(2) . . ?
F2 C9 S1 112.91(16) . . ?
F3 C9 S1 107.99(15) . . ?
F3 C9 F1 107.14(19) . . ?
F3 C9 F2 108.24(19) . . ?
C11 C10 C1 121.60(14) . . ?
C11 C10 C19 119.65(15) . . ?
C19 C10 C1 118.75(14) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.71(14) . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 121.40(15) . . ?
C13 C12 C17 119.28(15) . . ?
C17 C12 C11 119.31(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.49(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.67(16) . . ?
C15 C14 H14 120.7 . . ?
F4 C15 C14 116.96(15) . . ?
F4 C15 C16 118.87(17) . . ?
C16 C15 C14 124.16(17) . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.52(17) . . ?
C17 C16 H16 121.2 . . ?
C12 C17 C16 119.87(15) . . ?
C12 C17 C18 118.89(15) . . ?
C18 C17 C16 121.23(15) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.77(15) . . ?
C19 C18 H18 119.6 . . ?
C10 C19 H19 119.7 . . ?
C18 C19 C10 120.66(15) . . ?
C18 C19 H19 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 O1 54.1(2) . . . . ?
S1 C1 C2 O2 -126.82(13) . . . . ?
S1 C1 C3 C4 123.97(14) . . . . ?
S1 C1 C3 C8 -55.4(2) . . . . ?
S1 C1 C10 C11 123.19(15) . . . . ?
S1 C1 C10 C19 -56.68(18) . . . . ?
F4 C15 C16 C17 -178.51(14) . . . . ?
O2 C4 C5 C6 -177.7(2) . . . . ?
C1 S1 C9 F1 74.73(18) . . . . ?
C1 S1 C9 F2 -46.66(19) . . . . ?
C1 S1 C9 F3 -166.30(16) . . . . ?
C1 C3 C4 O2 -2.3(2) . . . . ?
C1 C3 C4 C5 178.9(2) . . . . ?
C1 C3 C8 C7 -180.0(2) . . . . ?
C1 C10 C11 C12 -179.27(14) . . . . ?
C1 C10 C19 C18 179.00(16) . . . . ?
C2 O2 C4 C3 -0.6(2) . . . . ?
C2 O2 C4 C5 178.3(2) . . . . ?
C2 C1 C3 C4 3.73(17) . . . . ?
C2 C1 C3 C8 -175.7(2) . . . . ?
C2 C1 C10 C11 -117.76(17) . . . . ?
C2 C1 C10 C19 62.4(2) . . . . ?
C3 C1 C2 O1 176.71(19) . . . . ?
C3 C1 C2 O2 -4.21(17) . . . . ?
C3 C1 C10 C11 -4.2(2) . . . . ?
C3 C1 C10 C19 175.92(16) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 O2 C2 O1 -177.73(18) . . . . ?
C4 O2 C2 C1 3.12(18) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C6 C7 C8 C3 0.7(4) . . . . ?
C8 C3 C4 O2 177.24(17) . . . . ?
C8 C3 C4 C5 -1.6(3) . . . . ?
C9 S1 C1 C2 63.83(14) . . . . ?
C9 S1 C1 C3 -50.44(15) . . . . ?
C9 S1 C1 C10 -178.80(12) . . . . ?
C10 C1 C2 O1 -60.0(2) . . . . ?
C10 C1 C2 O2 119.05(14) . . . . ?
C10 C1 C3 C4 -114.30(16) . . . . ?
C10 C1 C3 C8 66.3(3) . . . . ?
C10 C11 C12 C13 179.74(16) . . . . ?
C10 C11 C12 C17 0.4(2) . . . . ?
C11 C10 C19 C18 -0.9(3) . . . . ?
C11 C12 C13 C14 -178.81(16) . . . . ?
C11 C12 C17 C16 178.89(15) . . . . ?
C11 C12 C17 C18 -1.1(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C12 C17 C18 C19 0.8(3) . . . . ?
C13 C12 C17 C16 -0.5(2) . . . . ?
C13 C12 C17 C18 179.55(17) . . . . ?
C13 C14 C15 F4 178.58(16) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C15 C16 C17 C18 179.90(19) . . . . ?
C16 C17 C18 C19 -179.15(18) . . . . ?
C17 C12 C13 C14 0.6(3) . . . . ?
C17 C18 C19 C10 0.2(3) . . . . ?
C19 C10 C11 C12 0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_dm16808_0m
_database_code_depnum_ccdc_archive 'CCDC 1527561'
_audit_update_record             
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H15 F3 O5 S'
_chemical_formula_sum            'C15 H15 F3 O5 S'
_chemical_formula_weight         364.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5426(6)
_cell_length_b                   13.2312(10)
_cell_length_c                   15.9887(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1595.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16260
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.677
_diffrn_reflns_theta_min         1.998
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4558
_reflns_number_total             4902
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4902
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.0626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0719
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03845(5) 0.71746(3) 0.84596(2) 0.02321(9) Uani 1 1 d . . . . .
F1 F -0.04656(17) 0.89832(8) 0.90547(7) 0.0364(3) Uani 1 1 d . . . . .
F2 F 0.21335(16) 0.85105(10) 0.93741(7) 0.0402(3) Uani 1 1 d . . . . .
F3 F -0.0119(2) 0.77866(9) 0.99445(7) 0.0469(3) Uani 1 1 d . . . . .
O1 O 0.12548(19) 0.60268(8) 0.71092(8) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.44352(16) 0.70371(9) 0.80342(8) 0.0316(3) Uani 1 1 d . . . . .
O3 O 0.42266(15) 0.87171(8) 0.78623(8) 0.0256(2) Uani 1 1 d . . . . .
O4 O 0.21204(18) 0.79393(8) 0.35147(7) 0.0266(2) Uani 1 1 d . . . . .
O5 O 0.19749(19) 0.60678(8) 0.39224(7) 0.0280(3) Uani 1 1 d . . . . .
C1 C 0.16344(19) 0.77355(11) 0.75857(9) 0.0180(2) Uani 1 1 d . . . . .
C2 C 0.0828(2) 0.87289(11) 0.72653(10) 0.0202(3) Uani 1 1 d . . . . .
H2A H -0.0457 0.8632 0.7169 0.024 Uiso 1 1 calc R . . . .
H2B H 0.0973 0.9258 0.7697 0.024 Uiso 1 1 calc R . . . .
C3 C 0.1705(2) 0.90817(10) 0.64517(9) 0.0218(3) Uani 1 1 d . . . . .
H3A H 0.1028 0.9659 0.6221 0.026 Uiso 1 1 calc R . . . .
H3B H 0.2922 0.9318 0.6574 0.026 Uiso 1 1 calc R . . . .
C4 C 0.1784(2) 0.82504(11) 0.58066(9) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.1925(2) 0.85045(11) 0.49597(10) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.1974 0.9196 0.4802 0.024 Uiso 1 1 calc R . . . .
C6 C 0.1994(2) 0.77658(11) 0.43486(9) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.1915(2) 0.67259(11) 0.45787(9) 0.0206(3) Uani 1 1 d . . . . .
C8 C 0.1766(2) 0.64704(11) 0.54081(9) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.1702 0.5779 0.5566 0.024 Uiso 1 1 calc R . . . .
C9 C 0.17061(19) 0.72314(11) 0.60293(9) 0.0180(2) Uani 1 1 d . . . . .
C10 C 0.1504(2) 0.69035(11) 0.69051(9) 0.0196(3) Uani 1 1 d . . . . .
C11 C 0.36003(19) 0.77745(12) 0.78521(9) 0.0205(3) Uani 1 1 d . . . . .
C12 C 0.6059(2) 0.87979(15) 0.81359(13) 0.0325(4) Uani 1 1 d . . . . .
H12A H 0.6796 0.8333 0.7809 0.049 Uiso 1 1 calc GR . . . .
H12B H 0.6139 0.8623 0.8730 0.049 Uiso 1 1 calc GR . . . .
H12C H 0.6476 0.9492 0.8053 0.049 Uiso 1 1 calc GR . . . .
C13 C 0.0501(2) 0.81587(13) 0.92288(10) 0.0254(3) Uani 1 1 d . . . . .
C14 C 0.2012(3) 0.89736(12) 0.32504(11) 0.0295(4) Uani 1 1 d . . . . .
H14A H 0.2103 0.9008 0.2640 0.044 Uiso 1 1 calc GR . . . .
H14B H 0.2984 0.9359 0.3502 0.044 Uiso 1 1 calc GR . . . .
H14C H 0.0876 0.9260 0.3429 0.044 Uiso 1 1 calc GR . . . .
C15 C 0.1769(3) 0.50178(12) 0.41149(11) 0.0350(4) Uani 1 1 d . . . . .
H15A H 0.1848 0.4620 0.3599 0.053 Uiso 1 1 calc GR . . . .
H15B H 0.0609 0.4907 0.4376 0.053 Uiso 1 1 calc GR . . . .
H15C H 0.2707 0.4807 0.4501 0.053 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.8417(14) . ?
S1 C13 1.7933(17) . ?
F1 C13 1.341(2) . ?
F2 C13 1.337(2) . ?
F3 C13 1.3307(19) . ?
O1 C10 1.2197(18) . ?
O2 C11 1.1972(19) . ?
O3 C11 1.3337(19) . ?
O3 C12 1.453(2) . ?
O4 C6 1.3562(18) . ?
O4 C14 1.4346(18) . ?
O5 C7 1.3644(18) . ?
O5 C15 1.4314(19) . ?
C1 C2 1.536(2) . ?
C1 C10 1.551(2) . ?
C1 C11 1.544(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.509(2) . ?
C4 C5 1.399(2) . ?
C4 C9 1.3957(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 C7 1.426(2) . ?
C7 C8 1.373(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.4150(19) . ?
C9 C10 1.474(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S1 C1 101.69(7) . . ?
C11 O3 C12 114.16(13) . . ?
C6 O4 C14 116.55(12) . . ?
C7 O5 C15 116.77(12) . . ?
C2 C1 S1 113.28(10) . . ?
C2 C1 C10 110.37(12) . . ?
C2 C1 C11 116.34(12) . . ?
C10 C1 S1 102.35(9) . . ?
C11 C1 S1 107.20(10) . . ?
C11 C1 C10 106.16(11) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 111.91(12) . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.05(12) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C5 C4 C3 119.29(13) . . ?
C9 C4 C3 121.87(13) . . ?
C9 C4 C5 118.83(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.11(13) . . ?
C6 C5 H5 119.4 . . ?
O4 C6 C5 125.28(13) . . ?
O4 C6 C7 114.84(13) . . ?
C5 C6 C7 119.88(13) . . ?
O5 C7 C6 114.59(13) . . ?
O5 C7 C8 126.04(14) . . ?
C8 C7 C6 119.37(13) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.35(13) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 120.46(13) . . ?
C4 C9 C10 122.08(13) . . ?
C8 C9 C10 117.44(12) . . ?
O1 C10 C1 119.80(13) . . ?
O1 C10 C9 123.38(13) . . ?
C9 C10 C1 116.82(12) . . ?
O2 C11 O3 124.95(14) . . ?
O2 C11 C1 123.04(14) . . ?
O3 C11 C1 112.01(12) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F1 C13 S1 114.94(12) . . ?
F2 C13 S1 114.65(11) . . ?
F2 C13 F1 104.68(14) . . ?
F3 C13 S1 107.70(12) . . ?
F3 C13 F1 106.76(14) . . ?
F3 C13 F2 107.65(14) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -170.43(10) . . . . ?
S1 C1 C10 O1 -24.47(17) . . . . ?
S1 C1 C10 C9 155.91(11) . . . . ?
S1 C1 C11 O2 59.63(17) . . . . ?
S1 C1 C11 O3 -119.64(11) . . . . ?
O4 C6 C7 O5 -0.1(2) . . . . ?
O4 C6 C7 C8 -179.26(14) . . . . ?
O5 C7 C8 C9 -179.57(15) . . . . ?
C1 S1 C13 F1 70.77(14) . . . . ?
C1 S1 C13 F2 -50.63(14) . . . . ?
C1 S1 C13 F3 -170.41(12) . . . . ?
C1 C2 C3 C4 50.11(17) . . . . ?
C2 C1 C10 O1 -145.33(15) . . . . ?
C2 C1 C10 C9 35.06(17) . . . . ?
C2 C1 C11 O2 -172.42(14) . . . . ?
C2 C1 C11 O3 8.31(18) . . . . ?
C2 C3 C4 C5 157.00(14) . . . . ?
C2 C3 C4 C9 -22.5(2) . . . . ?
C3 C4 C5 C6 -179.73(14) . . . . ?
C3 C4 C9 C8 179.35(14) . . . . ?
C3 C4 C9 C10 1.3(2) . . . . ?
C4 C5 C6 O4 179.60(15) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C4 C9 C10 O1 172.40(16) . . . . ?
C4 C9 C10 C1 -8.0(2) . . . . ?
C5 C4 C9 C8 -0.1(2) . . . . ?
C5 C4 C9 C10 -178.16(14) . . . . ?
C5 C6 C7 O5 179.30(14) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C4 0.5(2) . . . . ?
C7 C8 C9 C10 178.65(15) . . . . ?
C8 C9 C10 O1 -5.7(2) . . . . ?
C8 C9 C10 C1 173.91(13) . . . . ?
C9 C4 C5 C6 -0.2(2) . . . . ?
C10 C1 C2 C3 -56.34(16) . . . . ?
C10 C1 C11 O2 -49.20(19) . . . . ?
C10 C1 C11 O3 131.53(12) . . . . ?
C11 C1 C2 C3 64.66(16) . . . . ?
C11 C1 C10 O1 87.78(17) . . . . ?
C11 C1 C10 C9 -91.84(15) . . . . ?
C12 O3 C11 O2 -1.2(2) . . . . ?
C12 O3 C11 C1 178.09(13) . . . . ?
C13 S1 C1 C2 -59.74(12) . . . . ?
C13 S1 C1 C10 -178.57(10) . . . . ?
C13 S1 C1 C11 69.97(11) . . . . ?
C14 O4 C6 C5 -5.9(2) . . . . ?
C14 O4 C6 C7 173.54(14) . . . . ?
C15 O5 C7 C6 -175.55(16) . . . . ?
C15 O5 C7 C8 3.5(3) . . . . ?

####################################################################### 
# 
# 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_mo_dm16829_0m
_database_code_depnum_ccdc_archive 'CCDC 1527562'
_audit_update_record             
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 F3 N2 O S'
_chemical_formula_sum            'C17 H11 F3 N2 O S'
_chemical_formula_weight         348.34
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5502(8)
_cell_length_b                   11.0835(11)
_cell_length_c                   16.8212(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1594.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5380
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.245
_cell_measurement_theta_min      2.200
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0444 before and 0.0379 after correction.
The Ratio of minimum to maximum transmission is 0.8538.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.801
_diffrn_reflns_theta_min         2.201
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4414
_reflns_number_total             4949
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.2850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1022
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33849(7) 0.33882(5) 0.55027(3) 0.02749(14) Uani 1 1 d . . . . .
F1 F 0.3443(5) 0.28827(19) 0.70208(11) 0.0976(12) Uani 1 1 d . . . . .
F2 F 0.1451(3) 0.2208(2) 0.6437(2) 0.1129(13) Uani 1 1 d . . . . .
F3 F 0.3681(2) 0.13914(14) 0.62364(10) 0.0484(5) Uani 1 1 d . . . . .
O1 O 0.47669(19) 0.56136(17) 0.66027(10) 0.0301(4) Uani 1 1 d . . . . .
N1 N 0.2276(2) 0.55224(17) 0.71190(10) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.7676(3) 0.6778(2) 0.37664(14) 0.0428(6) Uani 1 1 d . . . . .
C1 C 0.2538(3) 0.48559(19) 0.57955(12) 0.0197(4) Uani 1 1 d . . . . .
C2 C 0.3388(3) 0.53771(18) 0.65456(11) 0.0215(4) Uani 1 1 d . . . . .
C3 C 0.0796(3) 0.51369(19) 0.68631(12) 0.0206(4) Uani 1 1 d . . . . .
C4 C -0.0574(3) 0.5071(2) 0.73001(14) 0.0261(4) Uani 1 1 d . . . . .
H4 H -0.060445 0.531736 0.784077 0.031 Uiso 1 1 calc R . . . .
C5 C -0.1904(3) 0.4631(2) 0.69210(16) 0.0335(5) Uani 1 1 d . . . . .
H5 H -0.285964 0.457989 0.720706 0.040 Uiso 1 1 calc R . . . .
C6 C -0.1857(3) 0.4265(3) 0.61310(16) 0.0347(5) Uani 1 1 d . . . . .
H6 H -0.278239 0.398028 0.588099 0.042 Uiso 1 1 calc R . . . .
C7 C -0.0460(3) 0.4314(2) 0.57023(14) 0.0294(5) Uani 1 1 d . . . . .
H7 H -0.042167 0.404688 0.516591 0.035 Uiso 1 1 calc R . . . .
C8 C 0.0867(3) 0.4757(2) 0.60721(12) 0.0220(4) Uani 1 1 d . . . . .
C9 C 0.2606(3) 0.6052(2) 0.78953(14) 0.0330(5) Uani 1 1 d . . . . .
H9A H 0.201526 0.680399 0.795462 0.049 Uiso 1 1 calc GR . . . .
H9B H 0.372793 0.622209 0.793868 0.049 Uiso 1 1 calc GR . . . .
H9C H 0.229790 0.548502 0.831405 0.049 Uiso 1 1 calc GR . . . .
C10 C 0.2866(3) 0.56537(19) 0.50716(12) 0.0209(4) Uani 1 1 d . . . . .
C11 C 0.1683(3) 0.62261(19) 0.46503(12) 0.0250(4) Uani 1 1 d . . . . .
H11 H 0.062450 0.611270 0.480420 0.030 Uiso 1 1 calc R . . . .
C12 C 0.2034(3) 0.6969(2) 0.40012(14) 0.0308(5) Uani 1 1 d . . . . .
H12 H 0.121614 0.736594 0.372280 0.037 Uiso 1 1 calc R . . . .
C13 C 0.3565(3) 0.7125(2) 0.37651(13) 0.0308(5) Uani 1 1 d . . . . .
H13 H 0.380265 0.762310 0.332176 0.037 Uiso 1 1 calc R . . . .
C14 C 0.4767(3) 0.6546(2) 0.41813(13) 0.0266(4) Uani 1 1 d . . . . .
C15 C 0.4427(3) 0.5812(2) 0.48334(13) 0.0230(4) Uani 1 1 d . . . . .
H15 H 0.524735 0.542198 0.511451 0.028 Uiso 1 1 calc R . . . .
C16 C 0.6386(3) 0.6682(2) 0.39462(14) 0.0317(5) Uani 1 1 d . . . . .
C17 C 0.2962(4) 0.2445(2) 0.63409(18) 0.0459(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.848(2) . ?
S1 C17 1.793(3) . ?
F1 C17 1.309(4) . ?
F2 C17 1.327(4) . ?
F3 C17 1.331(3) . ?
O1 C2 1.212(3) . ?
N1 C2 1.364(3) . ?
N1 C3 1.403(3) . ?
N1 C9 1.459(3) . ?
N2 C16 1.149(4) . ?
C1 C2 1.566(3) . ?
C1 C8 1.506(3) . ?
C1 C10 1.531(3) . ?
C3 C4 1.385(3) . ?
C3 C8 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.388(3) . ?
C10 C15 1.405(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.399(3) . ?
C14 C15 1.396(3) . ?
C14 C16 1.448(4) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 S1 C1 102.99(11) . . ?
C2 N1 C3 112.06(17) . . ?
C2 N1 C9 123.1(2) . . ?
C3 N1 C9 124.85(19) . . ?
C2 C1 S1 110.95(14) . . ?
C8 C1 S1 112.95(15) . . ?
C8 C1 C2 102.59(16) . . ?
C8 C1 C10 117.48(18) . . ?
C10 C1 S1 102.99(13) . . ?
C10 C1 C2 110.04(17) . . ?
O1 C2 N1 126.6(2) . . ?
O1 C2 C1 126.5(2) . . ?
N1 C2 C1 106.85(18) . . ?
C4 C3 N1 128.0(2) . . ?
C4 C3 C8 121.8(2) . . ?
C8 C3 N1 110.15(18) . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(2) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.6 . . ?
C3 C8 C1 108.28(18) . . ?
C7 C8 C1 131.7(2) . . ?
C7 C8 C3 119.9(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 122.5(2) . . ?
C11 C10 C15 119.3(2) . . ?
C15 C10 C1 118.24(18) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C16 121.2(2) . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 C16 118.3(2) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
N2 C16 C14 179.1(3) . . ?
F1 C17 S1 114.0(2) . . ?
F1 C17 F2 105.8(3) . . ?
F1 C17 F3 107.2(3) . . ?
F2 C17 S1 114.0(2) . . ?
F2 C17 F3 107.0(3) . . ?
F3 C17 S1 108.32(18) . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_dm16474_0m
_database_code_depnum_ccdc_archive 'CCDC 1527558'
_audit_update_record             
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H14 Cl2 F3 N O2 S2'
_chemical_formula_sum            'C11 H14 Cl2 F3 N O2 S2'
_chemical_formula_weight         384.25
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7869(6)
_cell_length_b                   10.8732(8)
_cell_length_c                   8.8809(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.0620(10)
_cell_angle_gamma                90
_cell_volume                     749.00(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5654
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.67
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0304 after correction.
The Ratio of minimum to maximum transmission is 0.8871.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7661
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.672
_diffrn_reflns_theta_min         2.302
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                4364
_reflns_number_total             4461
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.3150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.045
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38790(7) 0.74665(6) 0.81159(7) 0.02368(12) Uani 1 1 d . . . . .
Cl2 Cl 0.44810(7) 1.00530(5) 0.81092(7) 0.02337(12) Uani 1 1 d . . . . .
S1 S 0.83086(9) 0.92786(10) 0.45223(8) 0.0406(2) Uani 1 1 d . . . . .
S2 S 0.46531(9) 0.97599(6) 0.44670(7) 0.02486(13) Uani 1 1 d . . . . .
F1 F 0.2163(2) 0.8526(2) 0.3153(2) 0.0472(5) Uani 1 1 d . . . . .
F2 F 0.4329(4) 0.8432(4) 0.1940(3) 0.0911(13) Uani 1 1 d . . . . .
F3 F 0.4275(5) 0.7403(2) 0.3960(4) 0.0936(13) Uani 1 1 d . . . . .
O1 O 0.8782(4) 1.0518(4) 0.4268(5) 0.0961(17) Uani 1 1 d . . . . .
O2 O 0.8084(3) 0.8469(5) 0.3265(3) 0.0933(17) Uani 1 1 d . . . . .
N1 N 0.6480(3) 0.9292(2) 0.5429(2) 0.0188(4) Uani 1 1 d . . . . .
C1 C 0.5556(3) 0.8603(2) 0.8051(2) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.6557(3) 0.8351(2) 0.6620(2) 0.0143(3) Uani 1 1 d . . . . .
H2 H 0.6195 0.7539 0.6169 0.017 Uiso 1 1 calc R . . . .
C3 C 0.9633(3) 0.8578(2) 0.6023(3) 0.0209(4) Uani 1 1 d . . . . .
H3A H 1.0161 0.7816 0.5664 0.025 Uiso 1 1 calc R . . . .
H3B H 1.0567 0.9146 0.6400 0.025 Uiso 1 1 calc R . . . .
C4 C 0.8481(3) 0.8281(2) 0.7282(2) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.8555(3) 0.9149(2) 0.8687(2) 0.0158(4) Uani 1 1 d . . . . .
C6 C 0.7004(3) 0.8494(2) 0.9346(2) 0.0181(4) Uani 1 1 d . . . . .
H6 H 0.6700 0.8833 1.0335 0.022 Uiso 1 1 calc R . . . .
C7 C 0.7629(3) 0.7139(2) 0.9418(3) 0.0231(5) Uani 1 1 d . . . . .
H7A H 0.6639 0.6565 0.9352 0.028 Uiso 1 1 calc R . . . .
H7B H 0.8359 0.6979 1.0368 0.028 Uiso 1 1 calc R . . . .
C8 C 0.8688(3) 0.7002(2) 0.8022(3) 0.0188(4) Uani 1 1 d . . . . .
H8A H 0.9913 0.6817 0.8332 0.023 Uiso 1 1 calc R . . . .
H8B H 0.8207 0.6349 0.7332 0.023 Uiso 1 1 calc R . . . .
C9 C 0.8401(3) 1.0533(2) 0.8309(3) 0.0230(5) Uani 1 1 d . . . . .
H9A H 0.8154 1.0990 0.9216 0.035 Uiso 1 1 calc GR . . . .
H9B H 0.7464 1.0660 0.7513 0.035 Uiso 1 1 calc GR . . . .
H9C H 0.9487 1.0826 0.7959 0.035 Uiso 1 1 calc GR . . . .
C10 C 1.0212(3) 0.9029(2) 0.9761(3) 0.0226(5) Uani 1 1 d . . . . .
H10A H 1.1186 0.9374 0.9275 0.034 Uiso 1 1 calc GR . . . .
H10B H 1.0433 0.8158 0.9991 0.034 Uiso 1 1 calc GR . . . .
H10C H 1.0070 0.9476 1.0699 0.034 Uiso 1 1 calc GR . . . .
C11 C 0.3875(3) 0.8455(3) 0.3310(3) 0.0273(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.802(2) . ?
Cl2 C1 1.788(2) . ?
S1 O1 1.420(4) . ?
S1 O2 1.420(4) . ?
S1 N1 1.697(2) . ?
S1 C3 1.782(3) . ?
S2 N1 1.673(2) . ?
S2 C11 1.824(3) . ?
F1 C11 1.331(3) . ?
F2 C11 1.297(3) . ?
F3 C11 1.306(4) . ?
N1 C2 1.469(3) . ?
C1 C2 1.573(3) . ?
C1 C6 1.543(3) . ?
C2 H2 1.0000 . ?
C2 C4 1.562(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.529(3) . ?
C4 C5 1.561(3) . ?
C4 C8 1.540(3) . ?
C5 C6 1.560(3) . ?
C5 C9 1.544(3) . ?
C5 C10 1.540(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.550(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.555(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 107.9(2) . . ?
O1 S1 C3 112.53(18) . . ?
O2 S1 O1 118.6(3) . . ?
O2 S1 N1 109.17(15) . . ?
O2 S1 C3 110.2(2) . . ?
N1 S1 C3 95.93(10) . . ?
N1 S2 C11 106.06(12) . . ?
S2 N1 S1 118.13(11) . . ?
C2 N1 S1 110.65(15) . . ?
C2 N1 S2 123.96(16) . . ?
Cl2 C1 Cl1 105.15(11) . . ?
C2 C1 Cl1 108.57(15) . . ?
C2 C1 Cl2 116.32(15) . . ?
C6 C1 Cl1 114.05(15) . . ?
C6 C1 Cl2 111.10(15) . . ?
C6 C1 C2 101.95(17) . . ?
N1 C2 C1 117.94(18) . . ?
N1 C2 H2 109.6 . . ?
N1 C2 C4 106.39(17) . . ?
C1 C2 H2 109.6 . . ?
C4 C2 C1 103.37(16) . . ?
C4 C2 H2 109.6 . . ?
S1 C3 H3A 110.2 . . ?
S1 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 S1 107.40(16) . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C3 C4 C2 108.62(17) . . ?
C3 C4 C5 118.27(19) . . ?
C3 C4 C8 117.20(19) . . ?
C5 C4 C2 103.78(16) . . ?
C8 C4 C2 105.41(17) . . ?
C8 C4 C5 102.09(17) . . ?
C6 C5 C4 92.77(17) . . ?
C9 C5 C4 114.75(18) . . ?
C9 C5 C6 118.60(19) . . ?
C10 C5 C4 114.42(18) . . ?
C10 C5 C6 111.27(18) . . ?
C10 C5 C9 105.18(19) . . ?
C1 C6 C5 102.97(17) . . ?
C1 C6 H6 114.3 . . ?
C1 C6 C7 108.07(19) . . ?
C5 C6 H6 114.3 . . ?
C7 C6 C5 101.46(18) . . ?
C7 C6 H6 114.3 . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C6 C7 C8 104.17(18) . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C4 C8 C7 102.15(17) . . ?
C4 C8 H8A 111.3 . . ?
C4 C8 H8B 111.3 . . ?
C7 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F1 C11 S2 107.09(19) . . ?
F2 C11 S2 116.0(2) . . ?
F2 C11 F1 104.9(2) . . ?
F2 C11 F3 108.9(3) . . ?
F3 C11 S2 112.22(18) . . ?
F3 C11 F1 107.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 N1 116.04(18) . . . . ?
Cl1 C1 C2 C4 -126.94(15) . . . . ?
Cl1 C1 C6 C5 157.24(15) . . . . ?
Cl1 C1 C6 C7 50.4(2) . . . . ?
Cl2 C1 C2 N1 -2.2(3) . . . . ?
Cl2 C1 C2 C4 114.78(17) . . . . ?
Cl2 C1 C6 C5 -84.13(18) . . . . ?
Cl2 C1 C6 C7 169.03(15) . . . . ?
S1 N1 C2 C1 150.09(16) . . . . ?
S1 N1 C2 C4 34.7(2) . . . . ?
S1 C3 C4 C2 15.7(2) . . . . ?
S1 C3 C4 C5 -102.1(2) . . . . ?
S1 C3 C4 C8 134.98(18) . . . . ?
S2 N1 C2 C1 -60.5(3) . . . . ?
S2 N1 C2 C4 -175.85(16) . . . . ?
O1 S1 N1 S2 69.5(2) . . . . ?
O1 S1 N1 C2 -139.0(2) . . . . ?
O1 S1 C3 C4 115.5(3) . . . . ?
O2 S1 N1 S2 -60.6(3) . . . . ?
O2 S1 N1 C2 90.8(3) . . . . ?
O2 S1 C3 C4 -109.6(2) . . . . ?
N1 S1 C3 C4 3.33(19) . . . . ?
N1 S2 C11 F1 149.20(19) . . . . ?
N1 S2 C11 F2 -94.1(3) . . . . ?
N1 S2 C11 F3 31.9(3) . . . . ?
N1 C2 C4 C3 -31.6(2) . . . . ?
N1 C2 C4 C5 95.10(19) . . . . ?
N1 C2 C4 C8 -157.96(17) . . . . ?
C1 C2 C4 C3 -156.46(18) . . . . ?
C1 C2 C4 C5 -29.8(2) . . . . ?
C1 C2 C4 C8 77.16(19) . . . . ?
C1 C6 C7 C8 73.7(2) . . . . ?
C2 C1 C6 C5 40.4(2) . . . . ?
C2 C1 C6 C7 -66.4(2) . . . . ?
C2 C4 C5 C6 52.07(18) . . . . ?
C2 C4 C5 C9 -71.3(2) . . . . ?
C2 C4 C5 C10 166.96(18) . . . . ?
C2 C4 C8 C7 -70.2(2) . . . . ?
C3 S1 N1 S2 -174.49(15) . . . . ?
C3 S1 N1 C2 -23.05(18) . . . . ?
C3 C4 C5 C6 172.42(19) . . . . ?
C3 C4 C5 C9 49.1(3) . . . . ?
C3 C4 C5 C10 -72.7(3) . . . . ?
C3 C4 C8 C7 168.83(19) . . . . ?
C4 C5 C6 C1 -56.80(19) . . . . ?
C4 C5 C6 C7 55.01(19) . . . . ?
C5 C4 C8 C7 37.9(2) . . . . ?
C5 C6 C7 C8 -34.2(2) . . . . ?
C6 C1 C2 N1 -123.3(2) . . . . ?
C6 C1 C2 C4 -6.2(2) . . . . ?
C6 C7 C8 C4 -2.2(2) . . . . ?
C8 C4 C5 C6 -57.34(18) . . . . ?
C8 C4 C5 C9 179.29(18) . . . . ?
C8 C4 C5 C10 57.5(2) . . . . ?
C9 C5 C6 C1 63.5(2) . . . . ?
C9 C5 C6 C7 175.26(19) . . . . ?
C10 C5 C6 C1 -174.38(18) . . . . ?
C10 C5 C6 C7 -62.6(2) . . . . ?
C11 S2 N1 S1 79.55(17) . . . . ?
C11 S2 N1 C2 -67.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_dm16194_0m
_database_code_depnum_ccdc_archive 'CCDC 1527557'
_audit_update_record             
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H20 F3 N O4 S2'
_chemical_formula_sum            'C13 H20 F3 N O4 S2'
_chemical_formula_weight         375.42
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.4266(17)
_cell_length_b                   8.8229(12)
_cell_length_c                   15.107(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.700(3)
_cell_angle_gamma                90
_cell_volume                     1594.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5461
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.317
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0746 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.9398.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16180
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.554
_diffrn_reflns_theta_min         1.400
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                8431
_reflns_number_total             9395
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 3438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         9395
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C14(H14), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C16(H16A,H16B), C17(H17A,H17B),
 C23(H23A,H23B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68624(6) 0.23618(8) 0.25730(5) 0.02081(15) Uani 1 1 d . . . . .
S2 S 0.57604(5) 0.27393(8) 0.39630(5) 0.01728(13) Uani 1 1 d . . . . .
F1 F 0.84809(19) 0.0995(3) 0.38195(15) 0.0417(5) Uani 1 1 d . . . . .
F2 F 0.90154(18) 0.1970(2) 0.27069(17) 0.0419(5) Uani 1 1 d . . . . .
F3 F 0.79877(19) -0.0004(2) 0.24655(16) 0.0418(5) Uani 1 1 d . . . . .
O1 O 0.59170(18) 0.1195(2) 0.42695(15) 0.0234(4) Uani 1 1 d . . . . .
O2 O 0.47254(17) 0.3120(3) 0.32961(14) 0.0244(5) Uani 1 1 d . . . . .
O3 O 0.88137(16) 0.4619(2) 0.36156(14) 0.0191(4) Uani 1 1 d . . . . .
O4 O 0.79317(19) 0.6795(2) 0.29249(14) 0.0222(4) Uani 1 1 d . . . . .
N1 N 0.68571(19) 0.3276(3) 0.35680(16) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.6904(2) 0.4953(3) 0.36296(18) 0.0159(5) Uani 1 1 d . . . . .
H1 H 0.6283 0.5403 0.3134 0.019 Uiso 1 1 calc R . . . .
C2 C 0.8035(2) 0.5758(3) 0.36493(19) 0.0168(5) Uani 1 1 d . . . . .
C3 C 0.8266(2) 0.6670(3) 0.45565(19) 0.0190(5) Uani 1 1 d . . . . .
H3 H 0.9042 0.7083 0.4774 0.023 Uiso 1 1 calc R . . . .
C4 C 0.7332(3) 0.7883(3) 0.4429(2) 0.0246(6) Uani 1 1 d . . . . .
H4A H 0.7186 0.8371 0.3818 0.030 Uiso 1 1 calc R . . . .
H4B H 0.7539 0.8672 0.4911 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6295(3) 0.6974(3) 0.4517(2) 0.0218(6) Uani 1 1 d . . . . .
H5A H 0.6068 0.7278 0.5071 0.026 Uiso 1 1 calc R . . . .
H5B H 0.5654 0.7109 0.3967 0.026 Uiso 1 1 calc R . . . .
C6 C 0.6731(2) 0.5332(3) 0.45953(19) 0.0168(5) Uani 1 1 d . . . . .
C7 C 0.7950(2) 0.5529(3) 0.52314(19) 0.0184(5) Uani 1 1 d . . . . .
C8 C 0.8632(2) 0.4063(3) 0.5440(2) 0.0204(5) Uani 1 1 d . . . . .
H8A H 0.8549 0.3491 0.4870 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.8361 0.3449 0.5876 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.9422 0.4310 0.5708 0.031 Uiso 1 1 calc GR . . . .
C9 C 0.7976(3) 0.6226(4) 0.6170(2) 0.0262(6) Uani 1 1 d . . . . .
H9A H 0.8752 0.6313 0.6544 0.039 Uiso 1 1 calc GR . . . .
H9B H 0.7559 0.5575 0.6487 0.039 Uiso 1 1 calc GR . . . .
H9C H 0.7633 0.7235 0.6079 0.039 Uiso 1 1 calc GR . . . .
C10 C 0.6013(2) 0.4109(3) 0.48672(19) 0.0184(5) Uani 1 1 d . . . . .
H10A H 0.5301 0.4543 0.4925 0.022 Uiso 1 1 calc R . . . .
H10B H 0.6412 0.3642 0.5461 0.022 Uiso 1 1 calc R . . . .
C11 C 0.9933(3) 0.5125(4) 0.3733(2) 0.0274(7) Uani 1 1 d . . . . .
H11A H 1.0339 0.4383 0.3464 0.041 Uiso 1 1 calc GR . . . .
H11B H 1.0304 0.5236 0.4391 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.9925 0.6105 0.3426 0.041 Uiso 1 1 calc GR . . . .
C12 C 0.7696(3) 0.6157(4) 0.2019(2) 0.0256(6) Uani 1 1 d . . . . .
H12A H 0.7630 0.6972 0.1567 0.038 Uiso 1 1 calc GR . . . .
H12B H 0.6993 0.5588 0.1888 0.038 Uiso 1 1 calc GR . . . .
H12C H 0.8305 0.5474 0.1983 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.8163(3) 0.1292(4) 0.2929(2) 0.0272(7) Uani 1 1 d . . . . .
S3 S 0.26242(6) 0.34256(8) 0.16022(5) 0.01948(14) Uani 1 1 d . . . . .
S4 S 0.39940(6) 0.46355(8) 0.05680(5) 0.01922(14) Uani 1 1 d . . . . .
F4 F 0.0958(2) 0.4090(4) 0.01675(18) 0.0709(10) Uani 1 1 d . . . . .
F5 F 0.04778(19) 0.3941(3) 0.1405(2) 0.0594(7) Uani 1 1 d . . . . .
F6 F 0.0874(2) 0.1929(3) 0.0803(2) 0.0560(7) Uani 1 1 d . . . . .
O5 O 0.49364(19) 0.3842(3) 0.11440(17) 0.0302(5) Uani 1 1 d . . . . .
O6 O 0.3420(2) 0.3953(3) -0.02858(15) 0.0337(6) Uani 1 1 d . . . . .
O7 O 0.28982(17) 0.7302(2) 0.31089(13) 0.0191(4) Uani 1 1 d . . . . .
O8 O 0.15830(16) 0.6758(2) 0.17390(14) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.30594(19) 0.5030(3) 0.11738(15) 0.0160(4) Uani 1 1 d . . . . .
C14 C 0.3513(2) 0.6312(3) 0.17900(18) 0.0152(5) Uani 1 1 d . . . . .
H14 H 0.4124 0.5949 0.2326 0.018 Uiso 1 1 calc R . . . .
C15 C 0.3999(2) 0.7442(3) 0.11977(18) 0.0154(5) Uani 1 1 d . . . . .
C16 C 0.4870(2) 0.8385(3) 0.18966(19) 0.0186(5) Uani 1 1 d . . . . .
H16A H 0.5309 0.9034 0.1588 0.022 Uiso 1 1 calc R . . . .
H16B H 0.5386 0.7731 0.2353 0.022 Uiso 1 1 calc R . . . .
C17 C 0.4115(2) 0.9356(3) 0.23547(19) 0.0196(6) Uani 1 1 d . . . . .
H17A H 0.4260 0.9108 0.3016 0.024 Uiso 1 1 calc R . . . .
H17B H 0.4245 1.0452 0.2290 0.024 Uiso 1 1 calc R . . . .
C18 C 0.2913(2) 0.8910(3) 0.18191(18) 0.0159(5) Uani 1 1 d . . . . .
H18 H 0.2335 0.9687 0.1842 0.019 Uiso 1 1 calc R . . . .
C19 C 0.2664(2) 0.7310(3) 0.21361(17) 0.0152(5) Uani 1 1 d . . . . .
C20 C 0.3034(2) 0.8599(3) 0.08331(18) 0.0167(5) Uani 1 1 d . . . . .
C21 C 0.2004(2) 0.7993(3) 0.01103(19) 0.0219(6) Uani 1 1 d . . . . .
H21A H 0.1788 0.7009 0.0311 0.033 Uiso 1 1 calc GR . . . .
H21B H 0.2182 0.7873 -0.0479 0.033 Uiso 1 1 calc GR . . . .
H21C H 0.1383 0.8709 0.0038 0.033 Uiso 1 1 calc GR . . . .
C22 C 0.3408(3) 1.0007(3) 0.0394(2) 0.0220(6) Uani 1 1 d . . . . .
H22A H 0.2780 1.0715 0.0203 0.033 Uiso 1 1 calc GR . . . .
H22B H 0.3654 0.9701 -0.0143 0.033 Uiso 1 1 calc GR . . . .
H22C H 0.4027 1.0501 0.0843 0.033 Uiso 1 1 calc GR . . . .
C23 C 0.4379(3) 0.6560(3) 0.0468(2) 0.0203(5) Uani 1 1 d . . . . .
H23A H 0.5198 0.6648 0.0574 0.024 Uiso 1 1 calc R . . . .
H23B H 0.4009 0.6955 -0.0153 0.024 Uiso 1 1 calc R . . . .
C24 C 0.2727(3) 0.5865(3) 0.3495(2) 0.0218(6) Uani 1 1 d . . . . .
H24A H 0.1977 0.5487 0.3187 0.033 Uiso 1 1 calc GR . . . .
H24B H 0.2798 0.5987 0.4154 0.033 Uiso 1 1 calc GR . . . .
H24C H 0.3287 0.5140 0.3410 0.033 Uiso 1 1 calc GR . . . .
C25 C 0.0688(2) 0.7688(4) 0.1858(2) 0.0256(6) Uani 1 1 d . . . . .
H25A H 0.0624 0.8594 0.1472 0.038 Uiso 1 1 calc GR . . . .
H25B H 0.0840 0.7989 0.2504 0.038 Uiso 1 1 calc GR . . . .
H25C H -0.0014 0.7116 0.1678 0.038 Uiso 1 1 calc GR . . . .
C26 C 0.1163(3) 0.3368(4) 0.0945(2) 0.0307(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.707(2) . ?
S1 C13 1.823(3) . ?
S2 O1 1.436(2) . ?
S2 O2 1.443(2) . ?
S2 N1 1.696(2) . ?
S2 C10 1.787(3) . ?
F1 C13 1.322(4) . ?
F2 C13 1.336(4) . ?
F3 C13 1.327(4) . ?
O3 C2 1.406(3) . ?
O3 C11 1.425(3) . ?
O4 C2 1.406(3) . ?
O4 C12 1.435(4) . ?
N1 C1 1.483(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.567(4) . ?
C1 C6 1.567(4) . ?
C2 C3 1.548(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.552(4) . ?
C3 C7 1.556(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.553(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.541(4) . ?
C6 C7 1.568(4) . ?
C6 C10 1.526(4) . ?
C7 C8 1.532(4) . ?
C7 C9 1.538(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S3 N2 1.704(2) . ?
S3 C26 1.819(3) . ?
S4 O5 1.438(2) . ?
S4 O6 1.427(2) . ?
S4 N2 1.698(2) . ?
S4 C23 1.781(3) . ?
F4 C26 1.299(4) . ?
F5 C26 1.335(4) . ?
F6 C26 1.321(4) . ?
O7 C19 1.419(3) . ?
O7 C24 1.436(3) . ?
O8 C19 1.401(3) . ?
O8 C25 1.432(3) . ?
N2 C14 1.477(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.565(4) . ?
C14 C19 1.569(4) . ?
C15 C16 1.536(4) . ?
C15 C20 1.558(4) . ?
C15 C23 1.525(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.564(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.544(4) . ?
C18 H18 1.0000 . ?
C18 C19 1.549(4) . ?
C18 C20 1.561(4) . ?
C20 C21 1.537(4) . ?
C20 C22 1.538(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C13 101.50(14) . . ?
O1 S2 O2 117.63(13) . . ?
O1 S2 N1 109.06(12) . . ?
O1 S2 C10 114.53(13) . . ?
O2 S2 N1 109.80(13) . . ?
O2 S2 C10 108.39(13) . . ?
N1 S2 C10 95.08(12) . . ?
C2 O3 C11 115.5(2) . . ?
C2 O4 C12 116.1(2) . . ?
S2 N1 S1 111.89(13) . . ?
C1 N1 S1 121.14(18) . . ?
C1 N1 S2 106.12(17) . . ?
N1 C1 H1 109.9 . . ?
N1 C1 C2 118.2(2) . . ?
N1 C1 C6 105.0(2) . . ?
C2 C1 H1 109.9 . . ?
C6 C1 H1 109.9 . . ?
C6 C1 C2 103.5(2) . . ?
O3 C2 O4 110.8(2) . . ?
O3 C2 C1 107.4(2) . . ?
O3 C2 C3 116.0(2) . . ?
O4 C2 C1 112.8(2) . . ?
O4 C2 C3 107.9(2) . . ?
C3 C2 C1 101.7(2) . . ?
C2 C3 H3 114.3 . . ?
C2 C3 C4 107.2(2) . . ?
C2 C3 C7 103.0(2) . . ?
C4 C3 H3 114.3 . . ?
C4 C3 C7 102.4(2) . . ?
C7 C3 H3 114.3 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C3 C4 C5 104.1(2) . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C4 C5 H5A 111.4 . . ?
C4 C5 H5B 111.4 . . ?
H5A C5 H5B 109.2 . . ?
C6 C5 C4 102.1(2) . . ?
C6 C5 H5A 111.4 . . ?
C6 C5 H5B 111.4 . . ?
C1 C6 C7 104.0(2) . . ?
C5 C6 C1 105.2(2) . . ?
C5 C6 C7 101.8(2) . . ?
C10 C6 C1 109.7(2) . . ?
C10 C6 C5 117.8(2) . . ?
C10 C6 C7 116.9(2) . . ?
C3 C7 C6 92.5(2) . . ?
C8 C7 C3 117.2(2) . . ?
C8 C7 C6 114.9(2) . . ?
C8 C7 C9 106.0(2) . . ?
C9 C7 C3 113.6(2) . . ?
C9 C7 C6 112.7(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S2 C10 H10A 110.6 . . ?
S2 C10 H10B 110.6 . . ?
C6 C10 S2 105.48(18) . . ?
C6 C10 H10A 110.6 . . ?
C6 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F1 C13 S1 113.5(2) . . ?
F1 C13 F2 107.8(3) . . ?
F1 C13 F3 109.1(3) . . ?
F2 C13 S1 113.2(2) . . ?
F3 C13 S1 106.5(2) . . ?
F3 C13 F2 106.4(3) . . ?
N2 S3 C26 100.85(14) . . ?
O5 S4 N2 109.73(13) . . ?
O5 S4 C23 108.77(15) . . ?
O6 S4 O5 117.86(15) . . ?
O6 S4 N2 109.03(13) . . ?
O6 S4 C23 113.94(15) . . ?
N2 S4 C23 95.11(12) . . ?
C19 O7 C24 114.5(2) . . ?
C19 O8 C25 115.7(2) . . ?
S4 N2 S3 111.61(13) . . ?
C14 N2 S3 120.22(18) . . ?
C14 N2 S4 107.23(16) . . ?
N2 C14 H14 110.0 . . ?
N2 C14 C15 105.6(2) . . ?
N2 C14 C19 117.6(2) . . ?
C15 C14 H14 110.0 . . ?
C15 C14 C19 103.4(2) . . ?
C19 C14 H14 110.0 . . ?
C16 C15 C14 105.1(2) . . ?
C16 C15 C20 102.7(2) . . ?
C20 C15 C14 103.9(2) . . ?
C23 C15 C14 109.3(2) . . ?
C23 C15 C16 118.4(2) . . ?
C23 C15 C20 116.0(2) . . ?
C15 C16 H16A 111.4 . . ?
C15 C16 H16B 111.4 . . ?
C15 C16 C17 101.8(2) . . ?
H16A C16 H16B 109.3 . . ?
C17 C16 H16A 111.4 . . ?
C17 C16 H16B 111.4 . . ?
C16 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C18 C17 C16 103.9(2) . . ?
C18 C17 H17A 111.0 . . ?
C18 C17 H17B 111.0 . . ?
C17 C18 H18 114.1 . . ?
C17 C18 C19 108.5(2) . . ?
C17 C18 C20 102.5(2) . . ?
C19 C18 H18 114.1 . . ?
C19 C18 C20 102.3(2) . . ?
C20 C18 H18 114.1 . . ?
O7 C19 C14 112.0(2) . . ?
O7 C19 C18 108.8(2) . . ?
O8 C19 O7 110.3(2) . . ?
O8 C19 C14 108.4(2) . . ?
O8 C19 C18 115.7(2) . . ?
C18 C19 C14 101.5(2) . . ?
C15 C20 C18 92.4(2) . . ?
C21 C20 C15 115.9(2) . . ?
C21 C20 C18 117.5(2) . . ?
C21 C20 C22 105.4(2) . . ?
C22 C20 C15 112.8(2) . . ?
C22 C20 C18 112.8(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S4 C23 H23A 110.4 . . ?
S4 C23 H23B 110.4 . . ?
C15 C23 S4 106.43(18) . . ?
C15 C23 H23A 110.4 . . ?
C15 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
O7 C24 H24A 109.5 . . ?
O7 C24 H24B 109.5 . . ?
O7 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O8 C25 H25A 109.5 . . ?
O8 C25 H25B 109.5 . . ?
O8 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F4 C26 S3 113.7(2) . . ?
F4 C26 F5 106.7(3) . . ?
F4 C26 F6 110.3(3) . . ?
F5 C26 S3 112.9(2) . . ?
F6 C26 S3 107.6(2) . . ?
F6 C26 F5 105.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A O3 0.98 2.24 2.868(3) 120.7 .
C21 H21A O8 0.98 2.25 2.865(4) 119.6 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -72.2(3) . . . . ?
S1 N1 C1 C6 173.14(17) . . . . ?
S2 N1 C1 C2 158.91(19) . . . . ?
S2 N1 C1 C6 44.2(2) . . . . ?
O1 S2 N1 S1 68.69(17) . . . . ?
O1 S2 N1 C1 -157.17(17) . . . . ?
O1 S2 C10 C6 134.00(19) . . . . ?
O2 S2 N1 S1 -61.54(17) . . . . ?
O2 S2 N1 C1 72.6(2) . . . . ?
O2 S2 C10 C6 -92.5(2) . . . . ?
O3 C2 C3 C4 178.3(2) . . . . ?
O3 C2 C3 C7 -74.2(3) . . . . ?
O4 C2 C3 C4 53.3(3) . . . . ?
O4 C2 C3 C7 160.8(2) . . . . ?
N1 S1 C13 F1 25.5(3) . . . . ?
N1 S1 C13 F2 -97.8(2) . . . . ?
N1 S1 C13 F3 145.6(2) . . . . ?
N1 S2 C10 C6 20.4(2) . . . . ?
N1 C1 C2 O3 -0.9(3) . . . . ?
N1 C1 C2 O4 121.4(3) . . . . ?
N1 C1 C2 C3 -123.3(2) . . . . ?
N1 C1 C6 C5 -157.2(2) . . . . ?
N1 C1 C6 C7 96.2(2) . . . . ?
N1 C1 C6 C10 -29.5(3) . . . . ?
C1 C2 C3 C4 -65.6(3) . . . . ?
C1 C2 C3 C7 42.0(3) . . . . ?
C1 C6 C7 C3 51.4(2) . . . . ?
C1 C6 C7 C8 -70.3(3) . . . . ?
C1 C6 C7 C9 168.2(2) . . . . ?
C1 C6 C10 S2 3.0(3) . . . . ?
C2 C1 C6 C5 78.3(2) . . . . ?
C2 C1 C6 C7 -28.3(3) . . . . ?
C2 C1 C6 C10 -154.1(2) . . . . ?
C2 C3 C4 C5 76.0(3) . . . . ?
C2 C3 C7 C6 -57.2(2) . . . . ?
C2 C3 C7 C8 62.5(3) . . . . ?
C2 C3 C7 C9 -173.3(2) . . . . ?
C3 C4 C5 C6 -4.9(3) . . . . ?
C4 C3 C7 C6 54.0(2) . . . . ?
C4 C3 C7 C8 173.7(2) . . . . ?
C4 C3 C7 C9 -62.1(3) . . . . ?
C4 C5 C6 C1 -68.3(3) . . . . ?
C4 C5 C6 C7 40.0(3) . . . . ?
C4 C5 C6 C10 169.1(2) . . . . ?
C5 C6 C7 C3 -57.8(2) . . . . ?
C5 C6 C7 C8 -179.4(2) . . . . ?
C5 C6 C7 C9 59.1(3) . . . . ?
C5 C6 C10 S2 123.2(2) . . . . ?
C6 C1 C2 O3 114.5(2) . . . . ?
C6 C1 C2 O4 -123.1(2) . . . . ?
C6 C1 C2 C3 -7.8(3) . . . . ?
C7 C3 C4 C5 -32.0(3) . . . . ?
C7 C6 C10 S2 -115.0(2) . . . . ?
C10 S2 N1 S1 -173.17(15) . . . . ?
C10 S2 N1 C1 -39.03(19) . . . . ?
C10 C6 C7 C3 172.5(2) . . . . ?
C10 C6 C7 C8 50.8(3) . . . . ?
C10 C6 C7 C9 -70.7(3) . . . . ?
C11 O3 C2 O4 63.3(3) . . . . ?
C11 O3 C2 C1 -173.1(2) . . . . ?
C11 O3 C2 C3 -60.2(3) . . . . ?
C12 O4 C2 O3 52.9(3) . . . . ?
C12 O4 C2 C1 -67.5(3) . . . . ?
C12 O4 C2 C3 -179.0(2) . . . . ?
C13 S1 N1 S2 -116.82(16) . . . . ?
C13 S1 N1 C1 116.8(2) . . . . ?
S3 N2 C14 C15 170.91(17) . . . . ?
S3 N2 C14 C19 -74.5(3) . . . . ?
S4 N2 C14 C15 42.1(2) . . . . ?
S4 N2 C14 C19 156.72(19) . . . . ?
O5 S4 N2 S3 -57.64(18) . . . . ?
O5 S4 N2 C14 76.0(2) . . . . ?
O5 S4 C23 C15 -95.1(2) . . . . ?
O6 S4 N2 S3 72.82(17) . . . . ?
O6 S4 N2 C14 -153.57(19) . . . . ?
O6 S4 C23 C15 131.2(2) . . . . ?
N2 S3 C26 F4 24.0(3) . . . . ?
N2 S3 C26 F5 -97.8(3) . . . . ?
N2 S3 C26 F6 146.4(3) . . . . ?
N2 S4 C23 C15 17.7(2) . . . . ?
N2 C14 C15 C16 -157.0(2) . . . . ?
N2 C14 C15 C20 95.4(2) . . . . ?
N2 C14 C15 C23 -29.0(3) . . . . ?
N2 C14 C19 O7 120.1(2) . . . . ?
N2 C14 C19 O8 -1.8(3) . . . . ?
N2 C14 C19 C18 -124.0(2) . . . . ?
C14 C15 C16 C17 -69.7(2) . . . . ?
C14 C15 C20 C18 52.2(2) . . . . ?
C14 C15 C20 C21 -70.1(3) . . . . ?
C14 C15 C20 C22 168.2(2) . . . . ?
C14 C15 C23 S4 4.4(3) . . . . ?
C15 C14 C19 O7 -124.1(2) . . . . ?
C15 C14 C19 O8 114.1(2) . . . . ?
C15 C14 C19 C18 -8.2(2) . . . . ?
C15 C16 C17 C18 -3.2(3) . . . . ?
C16 C15 C20 C18 -57.2(2) . . . . ?
C16 C15 C20 C21 -179.5(2) . . . . ?
C16 C15 C20 C22 58.8(3) . . . . ?
C16 C15 C23 S4 124.6(2) . . . . ?
C16 C17 C18 C19 74.7(2) . . . . ?
C16 C17 C18 C20 -33.1(3) . . . . ?
C17 C18 C19 O7 52.9(3) . . . . ?
C17 C18 C19 O8 177.6(2) . . . . ?
C17 C18 C19 C14 -65.3(2) . . . . ?
C17 C18 C20 C15 54.3(2) . . . . ?
C17 C18 C20 C21 175.3(2) . . . . ?
C17 C18 C20 C22 -61.8(3) . . . . ?
C19 C14 C15 C16 78.9(2) . . . . ?
C19 C14 C15 C20 -28.7(2) . . . . ?
C19 C14 C15 C23 -153.1(2) . . . . ?
C19 C18 C20 C15 -58.1(2) . . . . ?
C19 C18 C20 C21 62.9(3) . . . . ?
C19 C18 C20 C22 -174.1(2) . . . . ?
C20 C15 C16 C17 38.8(2) . . . . ?
C20 C15 C23 S4 -112.6(2) . . . . ?
C20 C18 C19 O7 160.7(2) . . . . ?
C20 C18 C19 O8 -74.6(3) . . . . ?
C20 C18 C19 C14 42.5(2) . . . . ?
C23 S4 N2 S3 -169.68(15) . . . . ?
C23 S4 N2 C14 -36.1(2) . . . . ?
C23 C15 C16 C17 168.0(2) . . . . ?
C23 C15 C20 C18 172.1(2) . . . . ?
C23 C15 C20 C21 49.8(3) . . . . ?
C23 C15 C20 C22 -71.9(3) . . . . ?
C24 O7 C19 O8 53.6(3) . . . . ?
C24 O7 C19 C14 -67.2(3) . . . . ?
C24 O7 C19 C18 -178.5(2) . . . . ?
C25 O8 C19 O7 67.1(3) . . . . ?
C25 O8 C19 C14 -170.0(2) . . . . ?
C25 O8 C19 C18 -56.9(3) . . . . ?
C26 S3 N2 S4 -113.09(17) . . . . ?
C26 S3 N2 C14 120.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
