# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_3c-OTf
_database_code_depnum_ccdc_archive 'CCDC 1519804'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_audit_creation_date             2016-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H12 N5 S, C F3 O3 S, C2 H3 N'
_chemical_formula_sum            'C13 H15 F3 N6 O3 S2'
_chemical_formula_weight         424.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H12F3O3N5S2
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2134(4)
_cell_length_b                   10.3216(7)
_cell_length_c                   14.0396(9)
_cell_angle_alpha                86.713(6)
_cell_angle_beta                 78.198(6)
_cell_angle_gamma                89.864(6)
_cell_volume                     879.87(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3077
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.8200
_cell_measurement_theta_min      3.8630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.2595
_exptl_crystal_size_mid          0.2133
_exptl_crystal_size_min          0.0385
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5350
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.969
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00   42.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305  -37.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00   12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -77.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   22.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305  -99.0000 -150.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0245301000
_diffrn_orient_matrix_UB_12      0.0060377000
_diffrn_orient_matrix_UB_13      0.0511486000
_diffrn_orient_matrix_UB_21      -0.1041110000
_diffrn_orient_matrix_UB_22      0.0261434000
_diffrn_orient_matrix_UB_23      -0.0032301000
_diffrn_orient_matrix_UB_31      -0.0464855000
_diffrn_orient_matrix_UB_32      -0.0633919000
_diffrn_orient_matrix_UB_33      0.0067998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2998
_reflns_number_total             3444
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.391
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.042
_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)+(0.0380P)²+0.3182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0950
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.58387(8) 0.57282(5) 0.38787(3) 0.01883(14) Uani 1 1 d . . . . .
N1 N 1.1483(3) 0.55078(18) 0.08286(13) 0.0198(4) Uani 1 1 d . . . . .
H1A H 1.198(4) 0.488(2) 0.1084(17) 0.024 Uiso 1 1 d R . . . .
H1B H 1.197(4) 0.570(2) 0.0220(17) 0.024 Uiso 1 1 d R . . . .
N2 N 0.8780(3) 0.57728(15) 0.22104(11) 0.0149(3) Uani 1 1 d . . . . .
N3 N 0.1765(3) 0.63072(16) 0.46118(12) 0.0182(4) Uani 1 1 d . . . . .
N4 N 0.2650(3) 0.88403(16) 0.50110(12) 0.0176(4) Uani 1 1 d . . . . .
N5 N 0.6224(3) 0.86659(18) 0.41978(13) 0.0201(4) Uani 1 1 d . . . . .
H5A H 0.645(4) 0.943(2) 0.4426(16) 0.024 Uiso 1 1 d R . . . .
H5B H 0.718(4) 0.827(2) 0.3884(17) 0.024 Uiso 1 1 d R . . . .
C1 C 0.9624(3) 0.60611(18) 0.12463(13) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.8527(3) 0.69516(19) 0.07245(14) 0.0193(4) Uani 1 1 d . . . . .
H2 H 0.9124 0.7191 0.0076 0.023 Uiso 1 1 calc R . . . .
C3 C 0.6592(3) 0.7462(2) 0.11712(15) 0.0217(5) Uani 1 1 d . . . . .
H3 H 0.5858 0.8045 0.0824 0.026 Uiso 1 1 calc R . . . .
C4 C 0.5696(3) 0.71175(19) 0.21474(14) 0.0194(4) Uani 1 1 d . . . . .
H4 H 0.4361 0.7460 0.2449 0.023 Uiso 1 1 calc R . . . .
C5 C 0.6796(3) 0.62752(18) 0.26532(14) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.3742(3) 0.68320(18) 0.43180(13) 0.0155(4) Uani 1 1 d . . . . .
C7 C 0.4239(3) 0.81193(18) 0.45003(13) 0.0152(4) Uani 1 1 d . . . . .
C8 C 0.0676(3) 0.8294(2) 0.53016(14) 0.0190(4) Uani 1 1 d . . . . .
H8 H -0.0442 0.8777 0.5657 0.023 Uiso 1 1 calc R . . . .
C9 C 0.0205(3) 0.7051(2) 0.51033(14) 0.0192(4) Uani 1 1 d . . . . .
H9 H -0.1216 0.6723 0.5313 0.023 Uiso 1 1 calc R . . . .
C10 C 1.0027(3) 0.4897(2) 0.27540(14) 0.0205(4) Uani 1 1 d . . . . .
H10A H 0.9813 0.4017 0.2602 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.9520 0.4982 0.3441 0.031 Uiso 1 1 calc GR . . . .
H10C H 1.1562 0.5118 0.2574 0.031 Uiso 1 1 calc GR . . . .
S2 S 0.54733(8) 0.25790(5) 0.13533(3) 0.01796(14) Uani 1 1 d . . . . .
F1 F 0.4152(2) 0.09118(13) 0.28252(10) 0.0402(4) Uani 1 1 d . . . . .
F2 F 0.7496(2) 0.15397(15) 0.26632(9) 0.0389(4) Uani 1 1 d . . . . .
F3 F 0.4871(2) 0.27931(13) 0.32368(9) 0.0386(4) Uani 1 1 d . . . . .
O1 O 0.3229(2) 0.29696(14) 0.14126(11) 0.0263(4) Uani 1 1 d . . . . .
O2 O 0.7031(3) 0.36372(16) 0.12158(11) 0.0326(4) Uani 1 1 d . . . . .
O3 O 0.6135(2) 0.15105(15) 0.07600(10) 0.0276(4) Uani 1 1 d . . . . .
C11 C 0.5498(4) 0.1923(2) 0.25856(15) 0.0225(5) Uani 1 1 d . . . . .
N6 N 0.0614(3) 0.84826(19) 0.27411(14) 0.0267(4) Uani 1 1 d . . . . .
C12 C 0.0754(3) 0.9151(2) 0.20540(15) 0.0207(4) Uani 1 1 d . . . . .
C13 C 0.0941(4) 0.9990(2) 0.11722(15) 0.0269(5) Uani 1 1 d . . . . .
H13A H 0.1629 1.0795 0.1256 0.040 Uiso 1 1 calc GR . . . .
H13B H -0.0498 1.0156 0.1045 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.1815 0.9572 0.0633 0.040 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 C5 1.762(2) . ?
S1 C6 1.767(2) . ?
N1 H1A 0.81(2) . ?
N1 H1B 0.86(2) . ?
N1 C1 1.328(3) . ?
N2 C1 1.364(2) . ?
N2 C5 1.376(2) . ?
N2 C10 1.470(3) . ?
N3 C6 1.320(3) . ?
N3 C9 1.338(3) . ?
N4 C7 1.346(2) . ?
N4 C8 1.327(3) . ?
N5 H5A 0.89(2) . ?
N5 H5B 0.79(2) . ?
N5 C7 1.335(3) . ?
C1 C2 1.403(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.361(3) . ?
C6 C7 1.414(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
S2 O1 1.4382(16) . ?
S2 O2 1.4393(15) . ?
S2 O3 1.4290(15) . ?
S2 C11 1.824(2) . ?
F1 C11 1.323(2) . ?
F2 C11 1.326(3) . ?
F3 C11 1.319(2) . ?
N6 C12 1.142(3) . ?
C12 C13 1.454(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C5 S1 C6 103.98(9) . . ?
H1A N1 H1B 119(2) . . ?
C1 N1 H1A 122.1(16) . . ?
C1 N1 H1B 117.3(16) . . ?
C1 N2 C5 120.60(17) . . ?
C1 N2 C10 118.15(16) . . ?
C5 N2 C10 121.25(16) . . ?
C6 N3 C9 116.93(17) . . ?
C8 N4 C7 117.17(17) . . ?
H5A N5 H5B 122(2) . . ?
C7 N5 H5A 117.4(14) . . ?
C7 N5 H5B 119.9(17) . . ?
N1 C1 N2 119.13(19) . . ?
N1 C1 C2 121.63(18) . . ?
N2 C1 C2 119.23(18) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.70(18) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.32(19) . . ?
C5 C4 H4 120.3 . . ?
N2 C5 S1 115.20(14) . . ?
C4 C5 S1 124.31(15) . . ?
C4 C5 N2 120.49(17) . . ?
N3 C6 S1 114.82(14) . . ?
N3 C6 C7 122.85(18) . . ?
C7 C6 S1 121.37(15) . . ?
N4 C7 C6 119.05(17) . . ?
N5 C7 N4 117.52(17) . . ?
N5 C7 C6 123.44(18) . . ?
N4 C8 H8 118.4 . . ?
N4 C8 C9 123.18(19) . . ?
C9 C8 H8 118.4 . . ?
N3 C9 C8 120.80(19) . . ?
N3 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 S2 O2 114.43(10) . . ?
O1 S2 C11 103.32(9) . . ?
O2 S2 C11 103.26(9) . . ?
O3 S2 O1 114.84(9) . . ?
O3 S2 O2 114.97(10) . . ?
O3 S2 C11 103.84(9) . . ?
F1 C11 S2 111.01(15) . . ?
F1 C11 F2 107.85(18) . . ?
F2 C11 S2 111.06(14) . . ?
F3 C11 S2 111.64(15) . . ?
F3 C11 F1 107.53(17) . . ?
F3 C11 F2 107.56(17) . . ?
N6 C12 C13 179.3(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
N1 H1A O1 0.81(2) 2.18(3) 2.969(2) 165(2) 1_655
N1 H1B O2 0.86(2) 2.06(2) 2.915(2) 173(2) 2_765
N5 H5A N4 0.89(2) 2.11(2) 3.001(2) 173(2) 2_676
N5 H5B N6 0.79(2) 2.39(2) 3.069(2) 144(2) 1_655

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 C6 C7 N4 -166.89(14) . . . . ?
S1 C6 C7 N5 12.6(3) . . . . ?
N1 C1 C2 C3 177.81(19) . . . . ?
N2 C1 C2 C3 -3.3(3) . . . . ?
N3 C6 C7 N4 1.3(3) . . . . ?
N3 C6 C7 N5 -179.21(19) . . . . ?
N4 C8 C9 N3 1.3(3) . . . . ?
C1 N2 C5 S1 175.94(13) . . . . ?
C1 N2 C5 C4 -3.2(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 S1 -178.60(15) . . . . ?
C3 C4 C5 N2 0.4(3) . . . . ?
C5 S1 C6 N3 118.06(15) . . . . ?
C5 S1 C6 C7 -72.85(17) . . . . ?
C5 N2 C1 N1 -176.52(17) . . . . ?
C5 N2 C1 C2 4.6(3) . . . . ?
C6 S1 C5 N2 165.04(14) . . . . ?
C6 S1 C5 C4 -15.90(19) . . . . ?
C6 N3 C9 C8 -1.1(3) . . . . ?
C7 N4 C8 C9 -0.2(3) . . . . ?
C8 N4 C7 N5 179.40(18) . . . . ?
C8 N4 C7 C6 -1.1(3) . . . . ?
C9 N3 C6 S1 168.74(14) . . . . ?
C9 N3 C6 C7 -0.2(3) . . . . ?
C10 N2 C1 N1 2.4(3) . . . . ?
C10 N2 C1 C2 -176.46(16) . . . . ?
C10 N2 C5 S1 -3.0(2) . . . . ?
C10 N2 C5 C4 177.91(17) . . . . ?
O1 S2 C11 F1 61.47(17) . . . . ?
O1 S2 C11 F2 -178.54(14) . . . . ?
O1 S2 C11 F3 -58.50(17) . . . . ?
O2 S2 C11 F1 -179.04(15) . . . . ?
O2 S2 C11 F2 -59.04(16) . . . . ?
O2 S2 C11 F3 61.00(17) . . . . ?
O3 S2 C11 F1 -58.72(17) . . . . ?
O3 S2 C11 F2 61.27(16) . . . . ?
O3 S2 C11 F3 -178.68(14) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 -14 5 0.1172 2.0038 -13.9905 4.9970 0.1220 -0.5905 0.8277
0 14 -3 0.0814 -0.0017 13.9837 -2.9987 -0.0689 0.3754 -0.9068
8 -4 8 0.1109 8.0083 -4.0223 7.9920 0.1881 -0.9647 -0.0629
-8 -8 -4 0.0864 -7.5056 -8.4650 -3.9927 -0.0712 0.5730 0.8584
-6 -10 -2 0.0947 -6.0036 -9.9684 -1.9939 -0.0149 0.3709 0.8974
3 13 9 0.1005 3.0090 12.9731 9.0082 0.4653 -0.0032 -0.9010
-4 -13 -1 0.1182 -3.5024 -13.4724 -0.9988 -0.0465 0.0157 1.0101
1 -1 -19 0.0132 0.9841 -0.9984 -19.0228 -1.0032 -0.0671 -0.1118
-1 1 19 0.0199 -1.4843 0.5006 19.0236 1.0125 0.1062 0.1666
2 3 -17 0.0213 1.9863 2.9932 -17.0212 -0.9013 -0.0736 -0.3978
-8 5 -8 0.1278 -8.0082 5.0211 -7.9917 -0.1820 0.9908 -0.0004

_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_4c-OTf
_database_code_depnum_ccdc_archive 'CCDC 1519805'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H12 N5 S, C F3 O3 S'
_chemical_formula_sum            'C11 H12 F3 N5 O3 S2'
_chemical_formula_weight         383.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H12N5O3S2F3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0148(4)
_cell_length_b                   20.0201(6)
_cell_length_c                   8.2625(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.096(5)
_cell_angle_gamma                90
_cell_volume                     1555.74(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2813
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.4090
_cell_measurement_theta_min      4.6940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.653
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 11 1 0.0364
3 5 3 0.0558
-6 -4 4 0.0459
5 5 -4 0.0772
-5 -2 -1 0.0140
5 3 1 0.0561
-1 -13 0 0.0279
3 -6 -4 0.0623
1 -7 4 0.0607
2 1 -5 0.0854
3 -11 0 0.0393
2 12 0 0.0453

_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.072
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.4996 10.9983 0.9967 -0.0775 -0.1796 -0.9839
2.9995 5.0125 3.0063 -0.9588 -0.1647 0.0259
-5.9964 -3.9986 3.9887 0.3742 -1.0025 -0.0874
5.4964 4.9979 -3.9893 -0.3459 0.9880 -0.0205
-5.4983 -2.0107 -1.0099 0.9048 -0.2255 -0.3598
5.4982 3.0108 1.0101 -0.9403 0.2416 0.2935
-0.9984 -13.0024 -0.0049 0.5887 -0.2704 0.7795
3.4982 -6.0058 -3.9954 0.2992 0.6887 0.5434
0.5018 -6.9894 3.9991 -0.3475 -0.6535 0.6509
1.9976 0.9900 -4.9963 0.3750 0.8526 -0.0817
3.0001 -10.9964 0.0025 0.0081 0.0062 0.9787
1.9981 12.0038 0.0063 -0.6806 0.3155 -0.6302

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5404
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         4.417
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  -8.00   1.00    6.00    --  -41.65 125.00 120.00   80
  2  ω   -116.00 -13.00   1.00    6.00    --  -41.65 -77.00  60.00  103
  3  ω     54.00  98.00   1.00    6.00    --   41.65-125.00 -60.00   44
  4  ω     86.00 178.00   1.00   22.50    --  112.00  45.00-150.00   92
  5  ω    138.00 178.00   1.00   22.50    --  112.00  45.00 120.00   40
  6  ω     37.00  69.00   1.00   22.50    --  112.00 -77.00 150.00   32
  7  ω     75.00 141.00   1.00   22.50    --  112.00 -77.00 150.00   66
  8  ω     87.00 119.00   1.00   22.50    --  112.00  45.00 120.00   32
  9  ω     38.00 140.00   1.00   22.50    --  112.00 -77.00 -30.00  102
 10  ω     36.00  68.00   1.00   22.50    --  112.00 -77.00 120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1271722000
_diffrn_orient_matrix_UB_12      -0.0354635000
_diffrn_orient_matrix_UB_13      -0.1329299000
_diffrn_orient_matrix_UB_21      0.0613582000
_diffrn_orient_matrix_UB_22      0.0161422000
_diffrn_orient_matrix_UB_23      -0.1429105000
_diffrn_orient_matrix_UB_31      0.0830158000
_diffrn_orient_matrix_UB_32      -0.0663420000
_diffrn_orient_matrix_UB_33      0.0363921000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2587
_reflns_number_total             2927
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.553
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.026
_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)+(0.0518P)²+1.3644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.39863(7) 0.27062(3) 0.17424(8) 0.04125(18) Uani 1 1 d . . . . .
N1 N 0.8188(2) 0.00667(12) 0.1197(3) 0.0462(5) Uani 1 1 d . . . . .
H1A H 0.840(3) 0.0363(17) 0.059(4) 0.055 Uiso 1 1 d R . . . .
H1B H 0.865(3) -0.0338(17) 0.131(4) 0.055 Uiso 1 1 d R . . . .
N2 N 0.6240(2) 0.06414(9) 0.1490(3) 0.0363(4) Uani 1 1 d . . . . .
N3 N 0.1744(2) 0.22964(10) 0.2526(3) 0.0400(5) Uani 1 1 d . . . . .
H3 H 0.153(3) 0.2732(16) 0.258(4) 0.048 Uiso 1 1 d R . . . .
N4 N 0.2431(2) 0.09778(10) 0.2680(3) 0.0427(5) Uani 1 1 d . . . . .
N5 N 0.4374(2) 0.12538(10) 0.1830(3) 0.0389(5) Uani 1 1 d . . . . .
H5 H 0.474(3) 0.1577(15) 0.155(4) 0.047 Uiso 1 1 d R . . . .
C1 C 0.7055(3) 0.00720(12) 0.1689(3) 0.0385(5) Uani 1 1 d . . . . .
C2 C 0.6700(3) -0.04908(12) 0.2461(3) 0.0407(5) Uani 1 1 d . . . . .
H2 H 0.7249 -0.0876 0.2617 0.049 Uiso 1 1 calc R . . . .
C3 C 0.5556(3) -0.04741(12) 0.2980(3) 0.0417(6) Uani 1 1 d . . . . .
H3A H 0.5333 -0.0850 0.3497 0.050 Uiso 1 1 calc R . . . .
C4 C 0.4708(3) 0.00936(11) 0.2756(3) 0.0404(5) Uani 1 1 d . . . . .
H4 H 0.3909 0.0094 0.3086 0.049 Uiso 1 1 calc R . . . .
C5 C 0.5071(3) 0.06523(11) 0.2039(3) 0.0359(5) Uani 1 1 d . . . . .
C6 C 0.2922(3) 0.21404(11) 0.2180(3) 0.0353(5) Uani 1 1 d . . . . .
C7 C 0.3195(3) 0.14233(11) 0.2250(3) 0.0353(5) Uani 1 1 d . . . . .
C8 C 0.1280(3) 0.11929(14) 0.3051(4) 0.0490(6) Uani 1 1 d . . . . .
H8 H 0.0724 0.0881 0.3365 0.059 Uiso 1 1 calc R . . . .
C9 C 0.0919(3) 0.18449(14) 0.2976(4) 0.0475(6) Uani 1 1 d . . . . .
H9 H 0.0125 0.1982 0.3226 0.057 Uiso 1 1 calc R . . . .
C10 C 0.6620(3) 0.12481(13) 0.0729(4) 0.0495(7) Uani 1 1 d . . . . .
H10A H 0.5806 0.1402 -0.0203 0.074 Uiso 1 1 calc GR . . . .
H10B H 0.7376 0.1147 0.0303 0.074 Uiso 1 1 calc GR . . . .
H10C H 0.6926 0.1590 0.1593 0.074 Uiso 1 1 calc GR . . . .
S2 S 0.93218(7) 0.36237(3) 0.30585(8) 0.04183(18) Uani 1 1 d . . . . .
F4 F 0.8590(3) 0.42834(15) 0.0208(3) 0.1057(9) Uani 1 1 d . . . . .
F5 F 0.8282(3) 0.32314(17) -0.0096(3) 0.1215(11) Uani 1 1 d . . . . .
F6 F 0.6858(2) 0.38113(14) 0.0730(4) 0.1025(9) Uani 1 1 d . . . . .
O1 O 1.0712(2) 0.35737(9) 0.2945(4) 0.0674(7) Uani 1 1 d . . . . .
O2 O 0.9114(3) 0.42343(11) 0.3853(3) 0.0709(7) Uani 1 1 d . . . . .
O3 O 0.8793(3) 0.30299(11) 0.3579(4) 0.0729(7) Uani 1 1 d . . . . .
C11 C 0.8210(4) 0.37414(18) 0.0872(4) 0.0622(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 C6 1.678(2) . ?
N1 H1A 0.84(3) . ?
N1 H1B 0.92(3) . ?
N1 C1 1.331(3) . ?
N2 C1 1.378(3) . ?
N2 C5 1.393(3) . ?
N2 C10 1.477(3) . ?
N3 H3 0.90(3) . ?
N3 C6 1.342(3) . ?
N3 C9 1.360(3) . ?
N4 C7 1.302(3) . ?
N4 C8 1.360(4) . ?
N5 H5 0.82(3) . ?
N5 C5 1.372(3) . ?
N5 C7 1.382(3) . ?
C1 C2 1.399(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.354(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C6 C7 1.459(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.350(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
S2 O1 1.431(2) . ?
S2 O2 1.436(2) . ?
S2 O3 1.427(2) . ?
S2 C11 1.783(3) . ?
F4 C11 1.329(4) . ?
F5 C11 1.314(4) . ?
F6 C11 1.325(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 117(3) . . ?
C1 N1 H1A 126(2) . . ?
C1 N1 H1B 115(2) . . ?
C1 N2 C5 120.2(2) . . ?
C1 N2 C10 120.2(2) . . ?
C5 N2 C10 119.6(2) . . ?
C6 N3 H3 118.4(19) . . ?
C6 N3 C9 124.3(2) . . ?
C9 N3 H3 116.9(19) . . ?
C7 N4 C8 117.9(2) . . ?
C5 N5 H5 118(2) . . ?
C5 N5 C7 128.7(2) . . ?
C7 N5 H5 113(2) . . ?
N1 C1 N2 120.1(2) . . ?
N1 C1 C2 120.6(2) . . ?
N2 C1 C2 119.2(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
N5 C5 N2 114.9(2) . . ?
C4 C5 N2 120.3(2) . . ?
C4 C5 N5 124.8(2) . . ?
N3 C6 S1 123.96(18) . . ?
N3 C6 C7 112.8(2) . . ?
C7 C6 S1 123.24(19) . . ?
N4 C7 N5 122.3(2) . . ?
N4 C7 C6 124.4(2) . . ?
N5 C7 C6 113.4(2) . . ?
N4 C8 H8 119.0 . . ?
C9 C8 N4 122.0(3) . . ?
C9 C8 H8 119.0 . . ?
N3 C9 H9 120.7 . . ?
C8 C9 N3 118.5(3) . . ?
C8 C9 H9 120.7 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 S2 O2 112.76(15) . . ?
O1 S2 C11 103.06(16) . . ?
O2 S2 C11 102.27(16) . . ?
O3 S2 O1 115.59(13) . . ?
O3 S2 O2 116.36(15) . . ?
O3 S2 C11 104.38(17) . . ?
F4 C11 S2 111.0(3) . . ?
F5 C11 S2 111.6(3) . . ?
F5 C11 F4 107.5(3) . . ?
F5 C11 F6 107.2(3) . . ?
F6 C11 S2 111.5(2) . . ?
F6 C11 F4 107.8(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
N1 H1A O2 0.84(3) 1.99(3) 2.793(3) 159(3) 4_565
N1 H1B O1 0.92(3) 2.29(4) 3.180(3) 161(3) 2_745
N1 H1B O2 0.92(3) 2.44(3) 3.187(4) 138(3) 2_745
N3 H3 O1 0.90(3) 1.94(3) 2.824(3) 165(3) 1_455
N5 H5 S1 0.82(3) 2.41(3) 2.931(2) 123(3) .
C4 H4 N4 0.93 2.26 2.871(3) 122.9 .

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 C6 C7 N4 175.96(19) . . . . ?
S1 C6 C7 N5 -3.3(3) . . . . ?
N1 C1 C2 C3 179.0(2) . . . . ?
N2 C1 C2 C3 0.9(4) . . . . ?
N3 C6 C7 N4 -3.1(3) . . . . ?
N3 C6 C7 N5 177.6(2) . . . . ?
N4 C8 C9 N3 -0.4(4) . . . . ?
C1 N2 C5 N5 177.7(2) . . . . ?
C1 N2 C5 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C3 C4 C5 N2 2.3(4) . . . . ?
C3 C4 C5 N5 -176.4(2) . . . . ?
C5 N2 C1 N1 -178.6(2) . . . . ?
C5 N2 C1 C2 -0.6(3) . . . . ?
C5 N5 C7 N4 -11.3(4) . . . . ?
C5 N5 C7 C6 168.0(2) . . . . ?
C6 N3 C9 C8 -1.4(4) . . . . ?
C7 N4 C8 C9 0.2(4) . . . . ?
C7 N5 C5 N2 -179.7(2) . . . . ?
C7 N5 C5 C4 -1.0(4) . . . . ?
C8 N4 C7 N5 -179.2(2) . . . . ?
C8 N4 C7 C6 1.6(4) . . . . ?
C9 N3 C6 S1 -176.1(2) . . . . ?
C9 N3 C6 C7 3.0(3) . . . . ?
C10 N2 C1 N1 0.0(4) . . . . ?
C10 N2 C1 C2 178.1(2) . . . . ?
C10 N2 C5 N5 -0.9(3) . . . . ?
C10 N2 C5 C4 -179.7(2) . . . . ?
O1 S2 C11 F4 -58.6(3) . . . . ?
O1 S2 C11 F5 61.3(3) . . . . ?
O1 S2 C11 F6 -178.8(3) . . . . ?
O2 S2 C11 F4 58.6(3) . . . . ?
O2 S2 C11 F5 178.5(3) . . . . ?
O2 S2 C11 F6 -61.7(3) . . . . ?
O3 S2 C11 F4 -179.7(2) . . . . ?
O3 S2 C11 F5 -59.9(3) . . . . ?
O3 S2 C11 F6 60.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.284
_oxdiff_exptl_absorpt_empirical_full_min 0.794
####################################################################### 
# 
# 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_5e-OTf
_database_code_depnum_ccdc_archive 'CCDC 1519808'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_5e-OTf              
;
PROBLEM: ALERT: Short Inter D...A Contact S1 .. O2 .. 2.74 Ang. 
RESPONSE: The short D...A contact is due to strong Coulombic cation...anion interaction.
;
# end Validation Reply Form

_audit_creation_date             2016-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H4 Cl2 N5 S3, C F3 O3 S'
_chemical_formula_sum            'C11 H4 Cl2 F3 N5 O3 S4'
_chemical_formula_weight         510.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1151(9)
_cell_length_b                   8.6552(10)
_cell_length_c                   12.6232(11)
_cell_angle_alpha                84.653(8)
_cell_angle_beta                 75.348(9)
_cell_angle_gamma                87.368(9)
_cell_volume                     853.83(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3093
_cell_measurement_temperature    293.97(10)
_cell_measurement_theta_max      28.3030
_cell_measurement_theta_min      3.5670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -9 -8 0.0399
-4 10 7 0.0450
6 9 -3 0.1019
7 3 16 0.0378
-8 -2 -16 0.0187
0 11 10 0.0446
-2 -9 10 0.0874
-4 -3 14 0.0846
3 -11 -4 0.0545
8 -9 4 0.0512
7 5 15 0.0359
9 -2 13 0.0415
3 3 18 0.0411
6 10 9 0.0545
9 -8 2 0.0384
-9 -8 -1 0.0758
-4 -1 -18 0.0347

_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9999 -8.9999 -7.9991 0.2630 -0.2435 0.9511
-3.9999 9.9999 6.9991 -0.1698 0.1342 -0.9792
5.9998 9.0001 -2.9999 0.6126 -0.5911 -0.4467
7.0002 2.9999 15.9995 0.6908 0.6350 -0.3305
-8.0002 -1.9999 -15.9996 -0.7608 -0.6476 0.2294
0.0001 10.9999 9.9991 0.1905 0.1827 -1.0005
-1.9997 -9.0001 9.9998 -0.2499 0.8933 0.4247
-3.9997 -3.0002 13.9993 -0.3191 0.9545 -0.1482
3.0000 -11.0000 -3.9993 0.0846 0.0853 0.9700
8.0001 -9.0000 4.0006 0.5623 0.3548 0.8085
7.0002 4.9999 14.9995 0.7141 0.5130 -0.4598
9.0002 -2.0001 13.0000 0.7777 0.5954 0.1498
3.0003 2.9998 17.9993 0.3644 0.8284 -0.4766
6.0000 10.0000 8.9995 0.6746 0.0362 -0.7448
9.0000 -8.0000 2.0007 0.6515 0.1904 0.7991
-8.9999 -8.0001 -1.0001 -0.8659 0.3998 0.3659
-4.0003 -0.9998 -17.9994 -0.4207 -0.8745 0.3014

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5803
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.010
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  88.00   1.00   20.00    --   19.23  57.00-180.00   88
  2  ω    -11.00  89.00   1.00   20.00    --   19.23  77.00 -60.00  100
  3  ω     23.00  59.00   1.00   20.00    --   19.23 -99.00  60.00   36
  4  ω     18.00  49.00   1.00   20.00    --   19.23 -99.00-150.00   31
  5  ω    -25.00  83.00   1.00   20.00    --   19.23  19.00 120.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0836320000
_diffrn_orient_matrix_UB_12      0.0136543000
_diffrn_orient_matrix_UB_13      0.0040274000
_diffrn_orient_matrix_UB_21      -0.0208135000
_diffrn_orient_matrix_UB_22      -0.0334471000
_diffrn_orient_matrix_UB_23      0.0550664000
_diffrn_orient_matrix_UB_31      0.0271791000
_diffrn_orient_matrix_UB_32      -0.0739809000
_diffrn_orient_matrix_UB_33      -0.0186780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2837
_reflns_number_total             3335
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.560
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.040
_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)+(0.0529P)²+1.3477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1146
_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:
 C3(H3)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c)
;
_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
Cl1 Cl 0.34171(11) 0.76215(10) 0.92648(7) 0.0247(2) Uani 1 1 d . . . . .
Cl2 Cl 0.60995(12) 1.03562(11) 0.86472(7) 0.0293(2) Uani 1 1 d . . . . .
S1 S 0.88998(11) 0.81005(9) 0.00091(6) 0.0183(2) Uani 1 1 d . . . . .
S2 S 0.70868(11) 0.65519(9) 0.08009(7) 0.0187(2) Uani 1 1 d . . . . .
S3 S 0.43198(11) 0.68440(10) 0.51439(7) 0.0195(2) Uani 1 1 d . . . . .
N1 N 0.9073(4) 0.8960(3) 0.1055(2) 0.0176(6) Uani 1 1 d . . . . .
N2 N 0.7225(3) 0.9272(3) 0.4805(2) 0.0160(6) Uani 1 1 d . . . . .
N3 N 0.8169(3) 0.9033(3) 0.2964(2) 0.0157(6) Uani 1 1 d . . . . .
N4 N 0.6579(3) 0.9653(3) 0.6644(2) 0.0183(6) Uani 1 1 d . . . . .
N5 N 0.4095(4) 0.7409(3) 0.7156(2) 0.0189(6) Uani 1 1 d . . . . .
C1 C 0.8115(4) 0.8420(4) 0.2007(3) 0.0155(6) Uani 1 1 d . . . . .
C2 C 0.6979(4) 0.7195(4) 0.2039(3) 0.0158(6) Uani 1 1 d . . . . .
C3 C 0.5860(4) 0.6673(4) 0.3037(3) 0.0182(7) Uani 1 1 d . . . . .
H3 H 0.5125 0.5867 0.3067 0.022 Uiso 1 1 calc R . . . .
C4 C 0.5868(4) 0.7370(4) 0.3962(3) 0.0155(6) Uani 1 1 d . . . . .
C5 C 0.4961(4) 0.7793(4) 0.6126(3) 0.0161(7) Uani 1 1 d . . . . .
C6 C 0.4479(4) 0.8140(4) 0.7935(3) 0.0181(7) Uani 1 1 d . . . . .
C7 C 0.5710(4) 0.9293(4) 0.7654(3) 0.0192(7) Uani 1 1 d . . . . .
C8 C 0.6252(4) 0.8887(3) 0.5846(3) 0.0162(7) Uani 1 1 d . . . . .
C9 C 0.7075(4) 0.8569(4) 0.3963(3) 0.0151(6) Uani 1 1 d . . . . .
C10 C 0.9463(4) 1.0202(4) 0.2925(3) 0.0235(8) Uani 1 1 d . . . . .
H10A H 0.8960 1.1224 0.2881 0.035 Uiso 1 1 calc GR . . . .
H10B H 1.0395 1.0095 0.2291 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.9874 1.0045 0.3577 0.035 Uiso 1 1 calc GR . . . .
S4 S 0.19395(10) 0.49007(9) 0.18691(7) 0.0181(2) Uani 1 1 d . . . . .
F1 F -0.0740(3) 0.4606(4) 0.3519(2) 0.0712(10) Uani 1 1 d . . . . .
F2 F 0.0864(5) 0.6392(3) 0.3621(2) 0.0686(10) Uani 1 1 d . . . . .
F3 F 0.1620(4) 0.4064(4) 0.39562(19) 0.0633(9) Uani 1 1 d . . . . .
O1 O 0.1803(4) 0.3311(3) 0.1675(2) 0.0355(7) Uani 1 1 d . . . . .
O2 O 0.0999(4) 0.5986(4) 0.1324(2) 0.0434(8) Uani 1 1 d . . . . .
O3 O 0.3641(3) 0.5312(4) 0.1817(2) 0.0378(7) Uani 1 1 d . . . . .
C11 C 0.0871(5) 0.4965(4) 0.3312(3) 0.0292(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
Cl1 C6 1.711(3) . ?
Cl2 C7 1.720(3) . ?
S1 S2 2.0366(12) . ?
S1 N1 1.613(3) . ?
S2 C2 1.687(3) . ?
S3 C4 1.729(3) . ?
S3 C5 1.743(3) . ?
N1 C1 1.312(4) . ?
N2 C8 1.371(4) . ?
N2 C9 1.307(4) . ?
N3 C1 1.375(4) . ?
N3 C9 1.382(4) . ?
N3 C10 1.480(4) . ?
N4 C7 1.308(4) . ?
N4 C8 1.341(4) . ?
N5 C5 1.332(4) . ?
N5 C6 1.324(4) . ?
C1 C2 1.429(4) . ?
C2 C3 1.403(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(4) . ?
C4 C9 1.460(4) . ?
C5 C8 1.401(4) . ?
C6 C7 1.402(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
S4 O1 1.435(3) . ?
S4 O2 1.421(3) . ?
S4 O3 1.426(3) . ?
S4 C11 1.814(4) . ?
F1 C11 1.313(5) . ?
F2 C11 1.329(5) . ?
F3 C11 1.314(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 S2 98.65(11) . . ?
C2 S2 S1 92.77(12) . . ?
C4 S3 C5 102.04(15) . . ?
C1 N1 S1 115.4(2) . . ?
C9 N2 C8 121.8(3) . . ?
C1 N3 C9 122.1(3) . . ?
C1 N3 C10 118.8(3) . . ?
C9 N3 C10 119.1(3) . . ?
C7 N4 C8 117.9(3) . . ?
C6 N5 C5 116.9(3) . . ?
N1 C1 N3 121.1(3) . . ?
N1 C1 C2 119.0(3) . . ?
N3 C1 C2 119.8(3) . . ?
C1 C2 S2 114.1(2) . . ?
C3 C2 S2 125.9(2) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 S3 117.5(2) . . ?
C3 C4 C9 122.3(3) . . ?
C9 C4 S3 120.2(2) . . ?
N5 C5 S3 114.2(2) . . ?
N5 C5 C8 123.3(3) . . ?
C8 C5 S3 122.5(3) . . ?
N5 C6 Cl1 117.4(3) . . ?
N5 C6 C7 120.0(3) . . ?
C7 C6 Cl1 122.6(3) . . ?
N4 C7 Cl2 116.6(3) . . ?
N4 C7 C6 123.0(3) . . ?
C6 C7 Cl2 120.4(3) . . ?
N2 C8 C5 125.4(3) . . ?
N4 C8 N2 115.8(3) . . ?
N4 C8 C5 118.8(3) . . ?
N2 C9 N3 116.0(3) . . ?
N2 C9 C4 127.1(3) . . ?
N3 C9 C4 116.8(3) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 S4 C11 103.46(17) . . ?
O2 S4 O1 115.02(19) . . ?
O2 S4 O3 115.86(19) . . ?
O2 S4 C11 104.02(17) . . ?
O3 S4 O1 113.01(18) . . ?
O3 S4 C11 103.36(18) . . ?
F1 C11 S4 112.0(3) . . ?
F1 C11 F2 105.3(3) . . ?
F1 C11 F3 109.4(3) . . ?
F2 C11 S4 110.9(3) . . ?
F3 C11 S4 112.6(2) . . ?
F3 C11 F2 106.4(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 C6 C7 Cl2 -4.9(4) . . . . ?
Cl1 C6 C7 N4 177.1(3) . . . . ?
S1 S2 C2 C1 -0.8(2) . . . . ?
S1 S2 C2 C3 176.8(3) . . . . ?
S1 N1 C1 N3 178.7(2) . . . . ?
S1 N1 C1 C2 -2.5(4) . . . . ?
S2 S1 N1 C1 1.6(2) . . . . ?
S2 C2 C3 C4 -176.5(2) . . . . ?
S3 C4 C9 N2 5.1(5) . . . . ?
S3 C4 C9 N3 -174.0(2) . . . . ?
S3 C5 C8 N2 -4.3(5) . . . . ?
S3 C5 C8 N4 174.9(2) . . . . ?
N1 C1 C2 S2 2.1(4) . . . . ?
N1 C1 C2 C3 -175.6(3) . . . . ?
N3 C1 C2 S2 -179.1(2) . . . . ?
N3 C1 C2 C3 3.2(5) . . . . ?
N5 C5 C8 N2 177.1(3) . . . . ?
N5 C5 C8 N4 -3.7(5) . . . . ?
N5 C6 C7 Cl2 174.9(2) . . . . ?
N5 C6 C7 N4 -3.1(5) . . . . ?
C1 N3 C9 N2 -178.1(3) . . . . ?
C1 N3 C9 C4 1.1(4) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C2 C3 C4 S3 173.2(2) . . . . ?
C2 C3 C4 C9 -4.1(5) . . . . ?
C3 C4 C9 N2 -177.7(3) . . . . ?
C3 C4 C9 N3 3.2(4) . . . . ?
C4 S3 C5 N5 -171.5(2) . . . . ?
C4 S3 C5 C8 9.8(3) . . . . ?
C5 S3 C4 C3 172.7(3) . . . . ?
C5 S3 C4 C9 -9.9(3) . . . . ?
C5 N5 C6 Cl1 -178.3(2) . . . . ?
C5 N5 C6 C7 1.9(4) . . . . ?
C6 N5 C5 S3 -177.3(2) . . . . ?
C6 N5 C5 C8 1.3(5) . . . . ?
C7 N4 C8 N2 -178.3(3) . . . . ?
C7 N4 C8 C5 2.4(4) . . . . ?
C8 N2 C9 N3 -178.0(3) . . . . ?
C8 N2 C9 C4 2.9(5) . . . . ?
C8 N4 C7 Cl2 -177.3(2) . . . . ?
C8 N4 C7 C6 0.8(5) . . . . ?
C9 N2 C8 N4 177.4(3) . . . . ?
C9 N2 C8 C5 -3.4(5) . . . . ?
C9 N3 C1 N1 174.6(3) . . . . ?
C9 N3 C1 C2 -4.2(4) . . . . ?
C10 N3 C1 N1 -6.6(5) . . . . ?
C10 N3 C1 C2 174.6(3) . . . . ?
C10 N3 C9 N2 3.1(4) . . . . ?
C10 N3 C9 C4 -177.7(3) . . . . ?
O1 S4 C11 F1 -61.7(3) . . . . ?
O1 S4 C11 F2 -179.0(3) . . . . ?
O1 S4 C11 F3 62.0(3) . . . . ?
O2 S4 C11 F1 58.8(3) . . . . ?
O2 S4 C11 F2 -58.4(3) . . . . ?
O2 S4 C11 F3 -177.5(3) . . . . ?
O3 S4 C11 F1 -179.8(3) . . . . ?
O3 S4 C11 F2 63.0(3) . . . . ?
O3 S4 C11 F3 -56.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.083
_oxdiff_exptl_absorpt_empirical_full_min 0.930
####################################################################### 
# 
# 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_5b-OTf
_database_code_depnum_ccdc_archive 'CCDC 1519806'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_5b-OTf              
;
PROBLEM: ALERT: Short Inter D...A Contact S1 .. O2 .. 2.70 Ang. 
RESPONSE: The short D...A contact is due to strong Coulombic cation...anion interaction.
;
# end Validation Reply Form

_audit_creation_date             2016-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H7 Cl N3 S3, C F3 O3 S'
_chemical_formula_sum            'C13 H7 Cl F3 N3 O3 S4'
_chemical_formula_weight         473.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H6 Cl N3 S4 O3 F3'
_chemical_oxdiff_usercomment     'ANR TBA-F 1:1 Ac-d6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4918(4)
_cell_length_b                   21.1396(9)
_cell_length_c                   11.7057(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.745(7)
_cell_angle_gamma                90
_cell_volume                     1847.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2144
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.4420
_cell_measurement_theta_min      6.2490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.542
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -13 2 0.0295
5 1 0 0.1115
2 -9 5 0.0531
0 -2 -7 0.0179
-1 8 6 0.0268
-5 -1 -1 0.0932
0 13 -2 0.0315
-1 -13 2 0.0336
2 -4 6 0.0535
0 -10 -5 0.0173

_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0013 -13.0096 2.0002 0.4478 -0.2260 0.8464
4.9981 1.0019 -0.0030 -0.7088 0.5835 0.4759
1.9972 -9.0132 4.9956 -0.1977 -0.2938 0.9785
0.0020 -1.9869 -6.9931 0.5582 0.7134 -0.2319
-1.0009 7.9912 5.9937 -0.6269 -0.7176 -0.2693
-4.9978 -0.9999 -0.9960 0.7757 -0.4812 -0.5254
0.0013 13.0096 -2.0002 -0.4478 0.2260 -0.8464
-1.0005 -13.0107 2.0003 0.5806 -0.3423 0.7398
1.9987 -4.0143 5.9956 -0.4886 -0.3880 0.7409
0.0002 -9.9944 -4.9954 0.7825 0.4957 0.3270

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6154
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.989
_diffrn_reflns_theta_min         6.287
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  77.00   1.00   15.00    --   41.40 -99.00 120.00   76
  2  ω     15.00 113.00   1.00   15.00    --   41.40  57.00  60.00   98
  3  ω      3.00  63.00   1.00   15.00    --   41.40 -99.00-120.00   60
  4  ω     29.00 101.00   1.00   65.00    --  112.00 -94.00  60.00   72
  5  ω     99.00 160.00   1.00   65.00    --  112.00 125.00 120.00   61
  6  ω     40.00 140.00   1.00   65.00    --  112.00 -30.00  90.00  100
  7  ω     63.00  99.00   1.00   65.00    --  112.00 -94.00-120.00   36
  8  ω     83.00 167.00   1.00   65.00    --  112.00  61.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1328811000
_diffrn_orient_matrix_UB_12      -0.0447300000
_diffrn_orient_matrix_UB_13      -0.0671518000
_diffrn_orient_matrix_UB_21      0.1163663000
_diffrn_orient_matrix_UB_22      0.0016082000
_diffrn_orient_matrix_UB_23      -0.1024366000
_diffrn_orient_matrix_UB_31      0.1067627000
_diffrn_orient_matrix_UB_32      -0.0574606000
_diffrn_orient_matrix_UB_33      0.0495126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2692
_reflns_number_total             3312
_reflns_odcompleteness_completeness 98.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         1.685
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0989
_refine_ls_restrained_S_all      1.195
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2731
_refine_ls_wR_factor_ref         0.2889
_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:
 C3(H3), C6(H6), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
_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
Cl1 Cl 0.15506(19) 0.17858(7) 0.36244(15) 0.0508(5) Uani 1 1 d . . . . .
S1 S 1.4666(2) 0.18562(6) -0.09106(15) 0.0470(5) Uani 1 1 d . . . . .
S2 S 1.3439(2) 0.10181(6) -0.05671(15) 0.0477(5) Uani 1 1 d . . . . .
S3 S 0.73988(19) 0.10640(6) 0.16244(15) 0.0469(5) Uani 1 1 d . . . . .
N1 N 1.3286(7) 0.2338(2) -0.0348(5) 0.0468(12) Uani 1 1 d . . . . .
N2 N 0.8062(7) 0.2525(2) 0.1445(5) 0.0445(11) Uani 1 1 d . . . . .
N3 N 1.0670(7) 0.2419(2) 0.0591(5) 0.0447(11) Uani 1 1 d . . . . .
C1 C 1.1936(8) 0.2067(3) 0.0102(6) 0.0437(13) Uani 1 1 d . . . . .
C2 C 1.1792(8) 0.1386(3) 0.0084(6) 0.0439(13) Uani 1 1 d . . . . .
C3 C 1.0387(8) 0.1087(3) 0.0575(6) 0.0460(14) Uani 1 1 d . . . . .
H3 H 1.0315 0.0648 0.0590 0.055 Uiso 1 1 calc R . . . .
C4 C 0.9111(8) 0.1451(3) 0.1037(6) 0.0436(13) Uani 1 1 d . . . . .
C5 C 0.6080(8) 0.1682(3) 0.2074(6) 0.0421(12) Uani 1 1 d . . . . .
C6 C 0.4528(8) 0.1518(3) 0.2573(6) 0.0477(14) Uani 1 1 d . . . . .
H6 H 0.4214 0.1095 0.2644 0.057 Uiso 1 1 calc R . . . .
C7 C 0.3459(8) 0.1987(3) 0.2962(6) 0.0467(13) Uani 1 1 d . . . . .
C8 C 0.3912(8) 0.2622(3) 0.2836(6) 0.0478(14) Uani 1 1 d . . . . .
H8 H 0.3190 0.2937 0.3107 0.057 Uiso 1 1 calc R . . . .
C9 C 0.5407(8) 0.2781(3) 0.2319(6) 0.0477(14) Uani 1 1 d . . . . .
H9 H 0.5671 0.3206 0.2214 0.057 Uiso 1 1 calc R . . . .
C10 C 0.6551(8) 0.2321(3) 0.1941(6) 0.0446(13) Uani 1 1 d . . . . .
C11 C 0.9210(8) 0.2140(3) 0.1044(5) 0.0432(13) Uani 1 1 d . . . . .
C12 C 1.0823(9) 0.3117(3) 0.0638(6) 0.0472(14) Uani 1 1 d . . . . .
H12A H 0.9805 0.3303 0.0213 0.071 Uiso 1 1 calc GR . . . .
H12B H 1.1898 0.3246 0.0311 0.071 Uiso 1 1 calc GR . . . .
H12C H 1.0865 0.3254 0.1422 0.071 Uiso 1 1 calc GR . . . .
S4 S 0.2626(2) 0.46100(6) 0.30644(16) 0.0529(5) Uani 1 1 d . . . . .
F1 F 0.1020(11) 0.4627(3) 0.0995(7) 0.112(2) Uani 1 1 d . . . . .
F2 F 0.3296(12) 0.5255(2) 0.1252(6) 0.119(3) Uani 1 1 d . . . . .
F3 F 0.3658(9) 0.4257(2) 0.1074(5) 0.0916(18) Uani 1 1 d . . . . .
O1 O 0.1568(8) 0.5122(2) 0.3414(6) 0.0691(15) Uani 1 1 d . . . . .
O2 O 0.1865(7) 0.3991(2) 0.3203(5) 0.0633(13) Uani 1 1 d . . . . .
O3 O 0.4522(7) 0.4657(2) 0.3434(6) 0.0689(15) Uani 1 1 d . . . . .
C13 C 0.2616(15) 0.4687(4) 0.1508(8) 0.075(2) 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 C7 1.735(6) . ?
S1 S2 2.051(2) . ?
S1 N1 1.628(5) . ?
S2 C2 1.693(6) . ?
S3 C4 1.712(6) . ?
S3 C5 1.746(5) . ?
N1 C1 1.311(8) . ?
N2 C10 1.384(8) . ?
N2 C11 1.300(8) . ?
N3 C1 1.368(8) . ?
N3 C11 1.385(8) . ?
N3 C12 1.480(7) . ?
C1 C2 1.444(8) . ?
C2 C3 1.391(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C4 C11 1.459(8) . ?
C5 C6 1.388(9) . ?
C5 C10 1.408(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(9) . ?
C7 C8 1.396(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.359(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
S4 O1 1.422(5) . ?
S4 O2 1.442(5) . ?
S4 O3 1.453(6) . ?
S4 C13 1.828(9) . ?
F1 C13 1.299(13) . ?
F2 C13 1.347(9) . ?
F3 C13 1.326(12) . ?

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 S2 98.71(19) . . ?
C2 S2 S1 92.7(2) . . ?
C4 S3 C5 103.0(3) . . ?
C1 N1 S1 115.2(4) . . ?
C11 N2 C10 123.1(5) . . ?
C1 N3 C11 121.7(5) . . ?
C1 N3 C12 120.2(5) . . ?
C11 N3 C12 118.1(5) . . ?
N1 C1 N3 121.0(5) . . ?
N1 C1 C2 119.3(5) . . ?
N3 C1 C2 119.7(5) . . ?
C1 C2 S2 114.1(5) . . ?
C3 C2 S2 125.6(5) . . ?
C3 C2 C1 120.3(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 S3 117.4(4) . . ?
C3 C4 C11 121.6(5) . . ?
C11 C4 S3 121.0(5) . . ?
C6 C5 S3 117.0(4) . . ?
C6 C5 C10 120.9(5) . . ?
C10 C5 S3 122.1(5) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.3(5) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 Cl1 119.7(5) . . ?
C6 C7 C8 120.4(6) . . ?
C8 C7 Cl1 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.1(6) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(6) . . ?
C10 C9 H9 119.3 . . ?
N2 C10 C5 124.5(5) . . ?
N2 C10 C9 117.6(5) . . ?
C9 C10 C5 117.9(6) . . ?
N2 C11 N3 116.0(5) . . ?
N2 C11 C4 126.3(5) . . ?
N3 C11 C4 117.7(5) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 S4 O2 115.0(3) . . ?
O1 S4 O3 114.6(3) . . ?
O1 S4 C13 105.2(4) . . ?
O2 S4 O3 114.5(3) . . ?
O2 S4 C13 102.9(4) . . ?
O3 S4 C13 102.4(5) . . ?
F1 C13 S4 112.3(8) . . ?
F1 C13 F2 109.5(8) . . ?
F1 C13 F3 107.8(8) . . ?
F2 C13 S4 109.3(6) . . ?
F3 C13 S4 111.5(6) . . ?
F3 C13 F2 106.2(8) . . ?

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 C7 C8 C9 179.9(5) . . . . ?
S1 S2 C2 C1 0.6(5) . . . . ?
S1 S2 C2 C3 -179.3(6) . . . . ?
S1 N1 C1 N3 -179.2(5) . . . . ?
S1 N1 C1 C2 0.9(8) . . . . ?
S2 S1 N1 C1 -0.4(5) . . . . ?
S2 C2 C3 C4 -177.6(5) . . . . ?
S3 C4 C11 N2 -1.7(9) . . . . ?
S3 C4 C11 N3 177.6(4) . . . . ?
S3 C5 C6 C7 178.8(5) . . . . ?
S3 C5 C10 N2 0.5(9) . . . . ?
S3 C5 C10 C9 179.5(5) . . . . ?
N1 C1 C2 S2 -1.1(8) . . . . ?
N1 C1 C2 C3 178.9(6) . . . . ?
N3 C1 C2 S2 179.1(5) . . . . ?
N3 C1 C2 C3 -1.0(10) . . . . ?
C1 N3 C11 N2 -177.5(6) . . . . ?
C1 N3 C11 C4 3.1(9) . . . . ?
C1 C2 C3 C4 2.4(10) . . . . ?
C2 C3 C4 S3 179.6(5) . . . . ?
C2 C3 C4 C11 -1.1(10) . . . . ?
C3 C4 C11 N2 179.1(6) . . . . ?
C3 C4 C11 N3 -1.6(9) . . . . ?
C4 S3 C5 C6 178.5(5) . . . . ?
C4 S3 C5 C10 -1.4(6) . . . . ?
C5 S3 C4 C3 -178.8(5) . . . . ?
C5 S3 C4 C11 1.9(6) . . . . ?
C5 C6 C7 Cl1 -178.1(5) . . . . ?
C5 C6 C7 C8 1.2(10) . . . . ?
C6 C5 C10 N2 -179.4(6) . . . . ?
C6 C5 C10 C9 -0.4(10) . . . . ?
C6 C7 C8 C9 0.6(10) . . . . ?
C7 C8 C9 C10 -2.4(10) . . . . ?
C8 C9 C10 N2 -178.7(6) . . . . ?
C8 C9 C10 C5 2.3(10) . . . . ?
C10 N2 C11 N3 -178.9(5) . . . . ?
C10 N2 C11 C4 0.4(10) . . . . ?
C10 C5 C6 C7 -1.3(10) . . . . ?
C11 N2 C10 C5 0.2(10) . . . . ?
C11 N2 C10 C9 -178.8(6) . . . . ?
C11 N3 C1 N1 178.3(6) . . . . ?
C11 N3 C1 C2 -1.9(9) . . . . ?
C12 N3 C1 N1 -1.2(9) . . . . ?
C12 N3 C1 C2 178.7(6) . . . . ?
C12 N3 C11 N2 2.0(8) . . . . ?
C12 N3 C11 C4 -177.4(6) . . . . ?
O1 S4 C13 F1 -62.9(7) . . . . ?
O1 S4 C13 F2 58.9(9) . . . . ?
O1 S4 C13 F3 176.0(6) . . . . ?
O2 S4 C13 F1 58.0(7) . . . . ?
O2 S4 C13 F2 179.7(7) . . . . ?
O2 S4 C13 F3 -63.1(7) . . . . ?
O3 S4 C13 F1 177.0(6) . . . . ?
O3 S4 C13 F2 -61.2(8) . . . . ?
O3 S4 C13 F3 55.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# 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_4f-OTf
_database_code_depnum_ccdc_archive 'CCDC 1536801'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_audit_creation_date             2017-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H14 N5 S, C F3 O3 S'
_chemical_formula_sum            'C15 H14 F3 N5 O3 S2'
_chemical_formula_weight         433.43
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1376(2)
_cell_length_b                   11.7508(5)
_cell_length_c                   13.2119(6)
_cell_angle_alpha                107.777(4)
_cell_angle_beta                 96.045(3)
_cell_angle_gamma                90.188(3)
_cell_volume                     901.69(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      28.1270
_cell_measurement_theta_min      3.6450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 17 0.0308
0 0 -18 0.0381
-6 -11 1 0.0568
4 -3 16 0.0443
-7 2 -8 0.0876
0 -9 -12 0.0192
8 -4 0 0.0638
-6 -1 14 0.0493
0 -13 16 0.0344
-1 -16 1 0.0216
2 16 -10 0.0213
0 15 2 0.0116

_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.039
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6674
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         3.208
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  54.00   1.00   72.50    --  -18.29   0.00-150.00  106
  2  ω    -87.00 -35.00   1.00   72.50    --  -18.29-178.00 -30.00   52
  3  ω    -29.00  15.00   1.00   72.50    --  -18.29 -87.00  77.00   44
  4  ω    -85.00   7.00   1.00   72.50    --  -18.29 -37.00-180.00   92
  5  ω      9.00  57.00   1.00   72.50    --   19.23 -99.00   0.00   48
  6  ω     -9.00  31.00   1.00   72.50    --   19.23  87.00-165.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3013
_reflns_number_total             3867
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.489
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.059
_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)+(0.0380P)²+0.4473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1033
_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:
 C2(H2), C3(H3A), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.21684(9) 0.56893(5) 0.48880(5) 0.01984(15) Uani 1 1 d . . . . .
N1 N -0.1560(4) 0.1296(2) 0.0283(2) 0.0250(5) Uani 1 1 d . . . . .
H1A H -0.243(4) 0.126(2) 0.072(2) 0.026(8) Uiso 1 1 d . . . . .
H1B H -0.178(4) 0.080(3) -0.033(2) 0.035(8) Uiso 1 1 d . . . . .
N2 N 0.0643(3) 0.28891(18) 0.14525(15) 0.0183(4) Uani 1 1 d . . . . .
N3 N 0.5655(3) 0.69058(18) 0.46806(17) 0.0178(4) Uani 1 1 d . . . . .
H3 H 0.565(4) 0.729(2) 0.532(2) 0.022(7) Uiso 1 1 d . . . . .
N4 N 0.5918(3) 0.55641(17) 0.25819(15) 0.0189(4) Uani 1 1 d . . . . .
N5 N 0.2771(3) 0.44680(18) 0.26644(16) 0.0194(4) Uani 1 1 d . . . . .
H5 H 0.196(4) 0.439(2) 0.311(2) 0.024(7) Uiso 1 1 d . . . . .
C1 C 0.0175(4) 0.2043(2) 0.04680(18) 0.0194(5) Uani 1 1 d . . . . .
C2 C 0.1526(4) 0.1984(2) -0.03371(19) 0.0253(6) Uani 1 1 d . . . . .
H2 H 0.1223 0.1400 -0.1019 0.030 Uiso 1 1 calc R . . . .
C3 C 0.3271(4) 0.2766(2) -0.0138(2) 0.0276(6) Uani 1 1 d . . . . .
H3A H 0.4178 0.2724 -0.0687 0.033 Uiso 1 1 calc R . . . .
C4 C 0.3757(4) 0.3627(2) 0.08562(19) 0.0250(6) Uani 1 1 d . . . . .
H4 H 0.4973 0.4173 0.0982 0.030 Uiso 1 1 calc R . . . .
C5 C 0.2456(4) 0.3675(2) 0.16512(18) 0.0177(5) Uani 1 1 d . . . . .
C6 C 0.4136(3) 0.6021(2) 0.42379(18) 0.0158(5) Uani 1 1 d . . . . .
C7 C 0.4386(4) 0.5350(2) 0.31096(18) 0.0163(5) Uani 1 1 d . . . . .
C8 C 0.7440(4) 0.6487(2) 0.31050(18) 0.0175(5) Uani 1 1 d . . . . .
C9 C 0.9139(4) 0.6733(2) 0.2561(2) 0.0223(5) Uani 1 1 d . . . . .
H9 H 0.9259 0.6259 0.1846 0.027 Uiso 1 1 calc R . . . .
C10 C 1.0634(4) 0.7663(2) 0.3064(2) 0.0252(6) Uani 1 1 d . . . . .
H10 H 1.1771 0.7834 0.2690 0.030 Uiso 1 1 calc R . . . .
C11 C 1.0485(4) 0.8355(2) 0.4119(2) 0.0245(6) Uani 1 1 d . . . . .
H11 H 1.1520 0.8996 0.4457 0.029 Uiso 1 1 calc R . . . .
C12 C 0.8864(4) 0.8121(2) 0.4675(2) 0.0215(5) Uani 1 1 d . . . . .
H12 H 0.8782 0.8588 0.5396 0.026 Uiso 1 1 calc R . . . .
C13 C 0.7335(3) 0.7187(2) 0.41632(18) 0.0173(5) Uani 1 1 d . . . . .
C14 C -0.0786(4) 0.2958(2) 0.23043(19) 0.0253(6) Uani 1 1 d . . . . .
H14A H 0.0000 0.2677 0.2862 0.038 Uiso 1 1 calc GR . . . .
H14B H -0.2116 0.2455 0.1998 0.038 Uiso 1 1 calc GR . . . .
H14C H -0.1189 0.3789 0.2616 0.038 Uiso 1 1 calc GR . . . .
S2 S 0.39580(9) 0.08206(5) 0.23127(4) 0.01847(15) Uani 1 1 d . . . . .
F1 F 0.4973(2) 0.00743(14) 0.39686(11) 0.0314(4) Uani 1 1 d . . . . .
F2 F 0.7731(2) 0.04003(16) 0.32076(13) 0.0388(4) Uani 1 1 d . . . . .
F3 F 0.5640(3) -0.11654(14) 0.24765(12) 0.0358(4) Uani 1 1 d . . . . .
O1 O 0.1862(3) 0.01949(17) 0.20876(15) 0.0314(5) Uani 1 1 d . . . . .
O2 O 0.5045(3) 0.07244(17) 0.13777(14) 0.0298(4) Uani 1 1 d . . . . .
O3 O 0.4038(3) 0.20057(16) 0.30648(14) 0.0308(4) Uani 1 1 d . . . . .
C15 C 0.5669(4) -0.0013(2) 0.30275(19) 0.0212(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
S1 C6 1.663(2) . ?
N1 H1A 0.84(3) . ?
N1 H1B 0.84(3) . ?
N1 C1 1.332(3) . ?
N2 C1 1.375(3) . ?
N2 C5 1.394(3) . ?
N2 C14 1.482(3) . ?
N3 H3 0.82(3) . ?
N3 C6 1.342(3) . ?
N3 C13 1.387(3) . ?
N4 C7 1.295(3) . ?
N4 C8 1.388(3) . ?
N5 H5 0.84(3) . ?
N5 C5 1.371(3) . ?
N5 C7 1.379(3) . ?
C1 C2 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.359(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.394(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(3) . ?
C6 C7 1.483(3) . ?
C8 C9 1.404(3) . ?
C8 C13 1.397(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S2 O1 1.4364(17) . ?
S2 O2 1.4397(18) . ?
S2 O3 1.4400(18) . ?
S2 C15 1.822(2) . ?
F1 C15 1.332(3) . ?
F2 C15 1.325(3) . ?
F3 C15 1.326(3) . ?

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
H1A N1 H1B 117(3) . . ?
C1 N1 H1A 126.6(19) . . ?
C1 N1 H1B 116(2) . . ?
C1 N2 C5 120.3(2) . . ?
C1 N2 C14 119.6(2) . . ?
C5 N2 C14 120.06(19) . . ?
C6 N3 H3 118.5(18) . . ?
C6 N3 C13 124.8(2) . . ?
C13 N3 H3 116.6(18) . . ?
C7 N4 C8 118.0(2) . . ?
C5 N5 H5 117.8(19) . . ?
C5 N5 C7 129.3(2) . . ?
C7 N5 H5 112.7(19) . . ?
N1 C1 N2 120.0(2) . . ?
N1 C1 C2 120.5(2) . . ?
N2 C1 C2 119.5(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
N5 C5 N2 115.0(2) . . ?
N5 C5 C4 124.9(2) . . ?
C4 C5 N2 120.1(2) . . ?
N3 C6 S1 123.64(18) . . ?
N3 C6 C7 113.6(2) . . ?
C7 C6 S1 122.78(17) . . ?
N4 C7 N5 122.9(2) . . ?
N4 C7 C6 124.7(2) . . ?
N5 C7 C6 112.4(2) . . ?
N4 C8 C9 119.5(2) . . ?
N4 C8 C13 122.0(2) . . ?
C13 C8 C9 118.6(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 118.9(2) . . ?
C13 C12 H12 120.5 . . ?
N3 C13 C8 117.0(2) . . ?
N3 C13 C12 121.7(2) . . ?
C12 C13 C8 121.3(2) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 S2 O2 113.98(11) . . ?
O1 S2 O3 115.52(11) . . ?
O1 S2 C15 103.91(11) . . ?
O2 S2 O3 114.47(12) . . ?
O2 S2 C15 103.66(11) . . ?
O3 S2 C15 103.18(11) . . ?
F1 C15 S2 111.01(16) . . ?
F2 C15 S2 110.84(17) . . ?
F2 C15 F1 107.88(19) . . ?
F2 C15 F3 108.05(19) . . ?
F3 C15 S2 111.36(16) . . ?
F3 C15 F1 107.5(2) . . ?

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 C6 C7 N4 -178.58(18) . . . . ?
S1 C6 C7 N5 2.3(3) . . . . ?
N1 C1 C2 C3 179.1(2) . . . . ?
N2 C1 C2 C3 -0.4(4) . . . . ?
N3 C6 C7 N4 0.8(3) . . . . ?
N3 C6 C7 N5 -178.32(19) . . . . ?
N4 C8 C9 C10 178.6(2) . . . . ?
N4 C8 C13 N3 1.2(3) . . . . ?
N4 C8 C13 C12 -179.2(2) . . . . ?
C1 N2 C5 N5 -179.2(2) . . . . ?
C1 N2 C5 C4 1.5(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 N2 -1.5(4) . . . . ?
C3 C4 C5 N5 179.3(2) . . . . ?
C5 N2 C1 N1 -179.9(2) . . . . ?
C5 N2 C1 C2 -0.5(3) . . . . ?
C5 N5 C7 N4 0.7(4) . . . . ?
C5 N5 C7 C6 179.8(2) . . . . ?
C6 N3 C13 C8 -0.3(3) . . . . ?
C6 N3 C13 C12 -179.9(2) . . . . ?
C7 N4 C8 C9 179.2(2) . . . . ?
C7 N4 C8 C13 -1.0(3) . . . . ?
C7 N5 C5 N2 -179.9(2) . . . . ?
C7 N5 C5 C4 -0.7(4) . . . . ?
C8 N4 C7 N5 179.0(2) . . . . ?
C8 N4 C7 C6 0.0(3) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C8 C13 N3 -179.0(2) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 N3 -180.0(2) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
C13 N3 C6 S1 178.78(17) . . . . ?
C13 N3 C6 C7 -0.6(3) . . . . ?
C13 C8 C9 C10 -1.2(3) . . . . ?
C14 N2 C1 N1 0.3(3) . . . . ?
C14 N2 C1 C2 179.7(2) . . . . ?
C14 N2 C5 N5 0.5(3) . . . . ?
C14 N2 C5 C4 -178.7(2) . . . . ?
O1 S2 C15 F1 -65.74(19) . . . . ?
O1 S2 C15 F2 174.39(16) . . . . ?
O1 S2 C15 F3 54.07(19) . . . . ?
O2 S2 C15 F1 174.85(16) . . . . ?
O2 S2 C15 F2 54.97(19) . . . . ?
O2 S2 C15 F3 -65.35(18) . . . . ?
O3 S2 C15 F1 55.19(19) . . . . ?
O3 S2 C15 F2 -64.68(19) . . . . ?
O3 S2 C15 F3 174.99(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1519807'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-10-04 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)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H7 Cl N3 S3'
_chemical_formula_sum            'C12 H7 Cl N3 S3'
_chemical_formula_weight         324.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H7 Cl N3 S3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9966(3)
_cell_length_b                   21.7939(5)
_cell_length_c                   10.4376(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.356(3)
_cell_angle_gamma                90
_cell_volume                     2468.19(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4138
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.6210
_cell_measurement_theta_min      4.0400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.375
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -9 -2 0.0475
1 -11 -4 0.0627
7 0 -2 0.0330
2 13 -3 0.0167
4 -2 5 0.0312
-7 -2 0 0.0250
4 9 -4 0.0213
3 12 -2 0.0165
3 13 -2 0.0148
4 2 5 0.0283
0 -10 5 0.0210
0 -13 3 0.0315
-4 -2 6 0.0309

_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.7172 -8.7211 -2.1424 -0.5628 -0.3873 0.7302
0.9998 -10.9996 -3.9998 0.1052 -0.8280 0.5094
6.9999 -0.0007 -1.9998 0.7764 -0.4330 -0.4362
2.0001 12.9997 -3.0001 -0.2097 -0.1146 -1.0131
4.0000 -2.0007 5.0000 0.8810 0.5096 0.0675
-6.9999 -1.9992 -0.0001 -0.8626 0.1195 0.4988
4.0000 8.9996 -4.0000 0.0693 -0.3957 -0.9010
3.0001 11.9995 -2.0000 0.0050 -0.0327 -0.9727
2.5079 12.5167 -2.4517 -0.0986 -0.0670 -0.9929
4.2065 1.6691 4.6936 0.8102 0.5570 -0.1825
0.0482 -10.1124 4.6704 0.5208 0.3573 0.7753
-0.0001 -12.9999 3.0001 0.4683 0.0660 0.9063
-3.9999 -1.9999 5.9998 -0.0890 0.8354 0.5259

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.993
_diffrn_reflns_theta_min         4.057
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00  -5.00   1.00   15.00    --  -41.65 125.00  90.00   90
  2  ω   -108.00 -18.00   1.00   15.00    --  -41.65 -77.00  30.00   90
  3  ω     54.00 136.00   1.00   45.00    --  106.66 -61.00  60.00   82
  4  ω    105.00 178.00   1.00   45.00    --  106.66 125.00  90.00   73
  5  ω    149.00 177.00   1.00   45.00    --  106.66  30.00 150.00   28
  6  ω     29.00 108.00   1.00   45.00    --  106.66 -94.00  30.00   79
  7  ω     78.00 175.00   1.00   45.00    --  106.66  30.00-120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1292858000
_diffrn_orient_matrix_UB_12      -0.0211889000
_diffrn_orient_matrix_UB_13      0.0642916000
_diffrn_orient_matrix_UB_21      -0.0242938000
_diffrn_orient_matrix_UB_22      0.0252608000
_diffrn_orient_matrix_UB_23      0.1314575000
_diffrn_orient_matrix_UB_31      -0.0534035000
_diffrn_orient_matrix_UB_32      -0.0625103000
_diffrn_orient_matrix_UB_33      0.0312077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3988
_reflns_number_total             4567
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         1.028
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.024
_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)+(0.0520P)²+1.4013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0994
_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:
 C3A(H3A), C6A(H6A), C8A(H8A), C9A(H9A), C3B(H3B), C6B(H6B), C8B(H8B), C9B(H9B)
2.b Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
;
_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
Cl1A Cl 0.59549(6) 0.26071(3) 0.76162(7) 0.03597(18) Uani 1 1 d . . . . .
S1A S -0.17137(6) 0.36095(3) -0.11862(7) 0.03420(17) Uani 1 1 d . . . . .
S2A S -0.19688(6) 0.29097(3) 0.01355(7) 0.03263(17) Uani 1 1 d . . . . .
S3A S 0.17460(6) 0.24858(3) 0.41954(6) 0.02693(15) Uani 1 1 d . . . . .
N1A N -0.0346(2) 0.38521(11) -0.0471(2) 0.0314(5) Uani 1 1 d . . . . .
N2A N 0.28871(19) 0.36110(10) 0.2909(2) 0.0238(4) Uani 1 1 d . . . . .
N3A N 0.1229(2) 0.37266(10) 0.1291(2) 0.0259(5) Uani 1 1 d . . . . .
C1A C 0.0097(2) 0.35599(12) 0.0600(2) 0.0258(5) Uani 1 1 d . . . . .
C2A C -0.0559(2) 0.30656(12) 0.1086(3) 0.0265(5) Uani 1 1 d . . . . .
C3A C -0.0049(2) 0.27511(13) 0.2188(3) 0.0268(5) Uani 1 1 d . . . . .
H3A H -0.0481 0.2433 0.2502 0.032 Uiso 1 1 calc R . . . .
C4A C 0.1116(2) 0.29118(12) 0.2829(2) 0.0234(5) Uani 1 1 d . . . . .
C5A C 0.3182(2) 0.28341(11) 0.4681(2) 0.0232(5) Uani 1 1 d . . . . .
C6A C 0.3926(2) 0.26022(12) 0.5780(3) 0.0266(5) Uani 1 1 d . . . . .
H6A H 0.3669 0.2268 0.6220 0.032 Uiso 1 1 calc R . . . .
C7A C 0.5050(2) 0.28746(12) 0.6209(3) 0.0268(5) Uani 1 1 d . . . . .
C8A C 0.5461(2) 0.33715(12) 0.5569(3) 0.0267(5) Uani 1 1 d . . . . .
H8A H 0.6225 0.3548 0.5867 0.032 Uiso 1 1 calc R . . . .
C9A C 0.4709(2) 0.36021(12) 0.4474(3) 0.0260(5) Uani 1 1 d . . . . .
H9A H 0.4976 0.3937 0.4043 0.031 Uiso 1 1 calc R . . . .
C10A C 0.3560(2) 0.33409(12) 0.4006(2) 0.0224(5) Uani 1 1 d . . . . .
C11A C 0.1798(2) 0.34117(12) 0.2397(2) 0.0229(5) Uani 1 1 d . . . . .
C12A C 0.1838(3) 0.42637(14) 0.0831(3) 0.0337(6) Uani 1 1 d . . . . .
H12A H 0.1806 0.4236 -0.0092 0.051 Uiso 1 1 calc GR . . . .
H12B H 0.2683 0.4276 0.1250 0.051 Uiso 1 1 calc GR . . . .
H12C H 0.1425 0.4630 0.1035 0.051 Uiso 1 1 calc GR . . . .
Cl1B Cl -0.43958(6) 0.39211(3) 0.12366(6) 0.03221(16) Uani 1 1 d . . . . .
S1B S 0.50362(6) 0.44515(3) 0.80054(7) 0.03280(17) Uani 1 1 d . . . . .
S2B S 0.37628(6) 0.37904(3) 0.84039(6) 0.03037(16) Uani 1 1 d . . . . .
S3B S -0.06217(6) 0.36256(3) 0.51490(6) 0.02705(16) Uani 1 1 d . . . . .
N1B N 0.4254(2) 0.47229(11) 0.6637(2) 0.0290(5) Uani 1 1 d . . . . .
N2B N 0.06324(19) 0.46617(10) 0.3687(2) 0.0231(4) Uani 1 1 d . . . . .
N3B N 0.24216(19) 0.46556(10) 0.5148(2) 0.0227(4) Uani 1 1 d . . . . .
C1B C 0.3166(2) 0.44705(12) 0.6281(2) 0.0243(5) Uani 1 1 d . . . . .
C2B C 0.2727(2) 0.40055(12) 0.7048(2) 0.0253(5) Uani 1 1 d . . . . .
C3B C 0.1562(2) 0.37575(12) 0.6684(3) 0.0264(5) Uani 1 1 d . . . . .
H3B H 0.1279 0.3453 0.7187 0.032 Uiso 1 1 calc R . . . .
C4B C 0.0824(2) 0.39648(11) 0.5569(2) 0.0225(5) Uani 1 1 d . . . . .
C5B C -0.1226(2) 0.40109(11) 0.3713(2) 0.0222(5) Uani 1 1 d . . . . .
C6B C -0.2398(2) 0.38415(12) 0.3116(3) 0.0252(5) Uani 1 1 d . . . . .
H6B H -0.2827 0.3536 0.3477 0.030 Uiso 1 1 calc R . . . .
C7B C -0.2922(2) 0.41292(12) 0.1981(3) 0.0254(5) Uani 1 1 d . . . . .
C8B C -0.2293(2) 0.45842(12) 0.1427(2) 0.0255(5) Uani 1 1 d . . . . .
H8B H -0.2653 0.4775 0.0662 0.031 Uiso 1 1 calc R . . . .
C9B C -0.1121(2) 0.47500(12) 0.2026(2) 0.0243(5) Uani 1 1 d . . . . .
H9B H -0.0702 0.5057 0.1658 0.029 Uiso 1 1 calc R . . . .
C10B C -0.0549(2) 0.44654(11) 0.3181(2) 0.0222(5) Uani 1 1 d . . . . .
C11B C 0.1234(2) 0.44272(11) 0.4756(2) 0.0227(5) Uani 1 1 d . . . . .
C12B C 0.2907(2) 0.50933(13) 0.4297(3) 0.0284(5) Uani 1 1 d . . . . .
H12D H 0.2928 0.4905 0.3469 0.043 Uiso 1 1 calc GR . . . .
H12E H 0.3726 0.5213 0.4681 0.043 Uiso 1 1 calc GR . . . .
H12F H 0.2386 0.5449 0.4182 0.043 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
Cl1A C7A 1.736(3) . ?
S1A S2A 2.1056(11) . ?
S1A N1A 1.653(2) . ?
S2A C2A 1.733(3) . ?
S3A C4A 1.748(3) . ?
S3A C5A 1.751(3) . ?
N1A C1A 1.310(4) . ?
N2A C10A 1.389(3) . ?
N2A C11A 1.304(3) . ?
N3A C1A 1.382(3) . ?
N3A C11A 1.400(3) . ?
N3A C12A 1.467(4) . ?
C1A C2A 1.434(4) . ?
C2A C3A 1.378(4) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.391(4) . ?
C4A C11A 1.436(4) . ?
C5A C6A 1.391(4) . ?
C5A C10A 1.409(4) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.378(4) . ?
C7A C8A 1.386(4) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.392(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.399(4) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
Cl1B C7B 1.740(3) . ?
S1B S2B 2.0974(10) . ?
S1B N1B 1.652(2) . ?
S2B C2B 1.731(3) . ?
S3B C4B 1.743(3) . ?
S3B C5B 1.752(3) . ?
N1B C1B 1.315(3) . ?
N2B C10B 1.388(3) . ?
N2B C11B 1.305(3) . ?
N3B C1B 1.384(3) . ?
N3B C11B 1.396(3) . ?
N3B C12B 1.463(3) . ?
C1B C2B 1.423(4) . ?
C2B C3B 1.385(4) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.383(4) . ?
C4B C11B 1.436(4) . ?
C5B C6B 1.387(3) . ?
C5B C10B 1.407(4) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.380(4) . ?
C7B C8B 1.388(4) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.386(4) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.409(4) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?

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
N1A S1A S2A 98.30(9) . . ?
C2A S2A S1A 91.77(10) . . ?
C4A S3A C5A 103.00(12) . . ?
C1A N1A S1A 114.5(2) . . ?
C11A N2A C10A 121.8(2) . . ?
C1A N3A C11A 123.0(2) . . ?
C1A N3A C12A 117.4(2) . . ?
C11A N3A C12A 119.6(2) . . ?
N1A C1A N3A 119.7(2) . . ?
N1A C1A C2A 121.9(2) . . ?
N3A C1A C2A 118.4(2) . . ?
C1A C2A S2A 113.5(2) . . ?
C3A C2A S2A 125.8(2) . . ?
C3A C2A C1A 120.6(2) . . ?
C2A C3A H3A 120.2 . . ?
C2A C3A C4A 119.7(3) . . ?
C4A C3A H3A 120.2 . . ?
C3A C4A S3A 118.1(2) . . ?
C3A C4A C11A 121.8(2) . . ?
C11A C4A S3A 120.10(19) . . ?
C6A C5A S3A 117.6(2) . . ?
C6A C5A C10A 121.0(2) . . ?
C10A C5A S3A 121.36(19) . . ?
C5A C6A H6A 120.4 . . ?
C7A C6A C5A 119.2(2) . . ?
C7A C6A H6A 120.4 . . ?
C6A C7A Cl1A 119.4(2) . . ?
C6A C7A C8A 121.7(2) . . ?
C8A C7A Cl1A 118.9(2) . . ?
C7A C8A H8A 120.6 . . ?
C7A C8A C9A 118.8(2) . . ?
C9A C8A H8A 120.6 . . ?
C8A C9A H9A 119.3 . . ?
C8A C9A C10A 121.5(2) . . ?
C10A C9A H9A 119.3 . . ?
N2A C10A C5A 125.7(2) . . ?
N2A C10A C9A 116.4(2) . . ?
C9A C10A C5A 117.9(2) . . ?
N2A C11A N3A 115.6(2) . . ?
N2A C11A C4A 128.0(2) . . ?
N3A C11A C4A 116.4(2) . . ?
N3A C12A H12A 109.5 . . ?
N3A C12A H12B 109.5 . . ?
N3A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N1B S1B S2B 98.45(9) . . ?
C2B S2B S1B 91.37(10) . . ?
C4B S3B C5B 102.41(12) . . ?
C1B N1B S1B 114.6(2) . . ?
C11B N2B C10B 121.2(2) . . ?
C1B N3B C11B 122.8(2) . . ?
C1B N3B C12B 119.1(2) . . ?
C11B N3B C12B 118.1(2) . . ?
N1B C1B N3B 120.2(2) . . ?
N1B C1B C2B 121.0(2) . . ?
N3B C1B C2B 118.7(2) . . ?
C1B C2B S2B 114.5(2) . . ?
C3B C2B S2B 125.1(2) . . ?
C3B C2B C1B 120.4(2) . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B C2B 119.6(2) . . ?
C4B C3B H3B 120.2 . . ?
C3B C4B S3B 117.36(19) . . ?
C3B C4B C11B 121.9(2) . . ?
C11B C4B S3B 120.68(19) . . ?
C6B C5B S3B 116.9(2) . . ?
C6B C5B C10B 121.5(2) . . ?
C10B C5B S3B 121.62(19) . . ?
C5B C6B H6B 120.3 . . ?
C7B C6B C5B 119.5(2) . . ?
C7B C6B H6B 120.3 . . ?
C6B C7B Cl1B 119.6(2) . . ?
C6B C7B C8B 121.0(2) . . ?
C8B C7B Cl1B 119.4(2) . . ?
C7B C8B H8B 120.4 . . ?
C9B C8B C7B 119.2(2) . . ?
C9B C8B H8B 120.4 . . ?
C8B C9B H9B 119.2 . . ?
C8B C9B C10B 121.7(2) . . ?
C10B C9B H9B 119.2 . . ?
N2B C10B C5B 126.1(2) . . ?
N2B C10B C9B 116.8(2) . . ?
C5B C10B C9B 117.1(2) . . ?
N2B C11B N3B 115.5(2) . . ?
N2B C11B C4B 128.0(2) . . ?
N3B C11B C4B 116.5(2) . . ?
N3B C12B H12D 109.5 . . ?
N3B C12B H12E 109.5 . . ?
N3B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
Cl1A C7A C8A C9A -177.2(2) . . . . ?
S1A S2A C2A C1A 0.27(19) . . . . ?
S1A S2A C2A C3A -177.8(2) . . . . ?
S1A N1A C1A N3A -179.35(19) . . . . ?
S1A N1A C1A C2A 0.8(3) . . . . ?
S2A S1A N1A C1A -0.5(2) . . . . ?
S2A C2A C3A C4A 177.5(2) . . . . ?
S3A C4A C11A N2A -0.4(4) . . . . ?
S3A C4A C11A N3A 179.66(18) . . . . ?
S3A C5A C6A C7A -178.4(2) . . . . ?
S3A C5A C10A N2A -1.1(4) . . . . ?
S3A C5A C10A C9A 178.53(19) . . . . ?
N1A C1A C2A S2A -0.7(3) . . . . ?
N1A C1A C2A C3A 177.4(3) . . . . ?
N3A C1A C2A S2A 179.44(19) . . . . ?
N3A C1A C2A C3A -2.4(4) . . . . ?
C1A N3A C11A N2A 177.4(2) . . . . ?
C1A N3A C11A C4A -2.7(4) . . . . ?
C1A C2A C3A C4A -0.5(4) . . . . ?
C2A C3A C4A S3A -178.2(2) . . . . ?
C2A C3A C4A C11A 1.8(4) . . . . ?
C3A C4A C11A N2A 179.6(3) . . . . ?
C3A C4A C11A N3A -0.3(4) . . . . ?
C4A S3A C5A C6A 179.2(2) . . . . ?
C4A S3A C5A C10A 0.8(2) . . . . ?
C5A S3A C4A C3A 179.9(2) . . . . ?
C5A S3A C4A C11A -0.1(2) . . . . ?
C5A C6A C7A Cl1A 177.4(2) . . . . ?
C5A C6A C7A C8A -0.4(4) . . . . ?
C6A C5A C10A N2A -179.4(2) . . . . ?
C6A C5A C10A C9A 0.2(4) . . . . ?
C6A C7A C8A C9A 0.6(4) . . . . ?
C7A C8A C9A C10A -0.4(4) . . . . ?
C8A C9A C10A N2A 179.7(2) . . . . ?
C8A C9A C10A C5A 0.0(4) . . . . ?
C10A N2A C11A N3A -179.8(2) . . . . ?
C10A N2A C11A C4A 0.3(4) . . . . ?
C10A C5A C6A C7A 0.0(4) . . . . ?
C11A N2A C10A C5A 0.5(4) . . . . ?
C11A N2A C10A C9A -179.1(2) . . . . ?
C11A N3A C1A N1A -175.8(2) . . . . ?
C11A N3A C1A C2A 4.0(4) . . . . ?
C12A N3A C1A N1A 4.8(4) . . . . ?
C12A N3A C1A C2A -175.3(2) . . . . ?
C12A N3A C11A N2A -3.2(4) . . . . ?
C12A N3A C11A C4A 176.7(2) . . . . ?
Cl1B C7B C8B C9B 179.7(2) . . . . ?
S1B S2B C2B C1B 2.91(19) . . . . ?
S1B S2B C2B C3B -177.8(2) . . . . ?
S1B N1B C1B N3B -179.68(18) . . . . ?
S1B N1B C1B C2B 0.5(3) . . . . ?
S2B S1B N1B C1B 1.4(2) . . . . ?
S2B C2B C3B C4B -179.3(2) . . . . ?
S3B C4B C11B N2B 2.1(4) . . . . ?
S3B C4B C11B N3B -177.75(18) . . . . ?
S3B C5B C6B C7B -180.0(2) . . . . ?
S3B C5B C10B N2B 0.2(4) . . . . ?
S3B C5B C10B C9B -179.66(19) . . . . ?
N1B C1B C2B S2B -2.8(3) . . . . ?
N1B C1B C2B C3B 177.9(2) . . . . ?
N3B C1B C2B S2B 177.43(18) . . . . ?
N3B C1B C2B C3B -1.9(4) . . . . ?
C1B N3B C11B N2B 177.8(2) . . . . ?
C1B N3B C11B C4B -2.3(3) . . . . ?
C1B C2B C3B C4B -0.1(4) . . . . ?
C2B C3B C4B S3B 179.0(2) . . . . ?
C2B C3B C4B C11B 0.9(4) . . . . ?
C3B C4B C11B N2B -179.9(3) . . . . ?
C3B C4B C11B N3B 0.2(4) . . . . ?
C4B S3B C5B C6B 179.9(2) . . . . ?
C4B S3B C5B C10B 0.7(2) . . . . ?
C5B S3B C4B C3B -179.7(2) . . . . ?
C5B S3B C4B C11B -1.7(2) . . . . ?
C5B C6B C7B Cl1B -179.6(2) . . . . ?
C5B C6B C7B C8B 0.2(4) . . . . ?
C6B C5B C10B N2B -179.0(2) . . . . ?
C6B C5B C10B C9B 1.2(4) . . . . ?
C6B C7B C8B C9B 0.0(4) . . . . ?
C7B C8B C9B C10B 0.4(4) . . . . ?
C8B C9B C10B N2B 179.1(2) . . . . ?
C8B C9B C10B C5B -1.0(4) . . . . ?
C10B N2B C11B N3B 178.8(2) . . . . ?
C10B N2B C11B C4B -1.1(4) . . . . ?
C10B C5B C6B C7B -0.8(4) . . . . ?
C11B N2B C10B C5B -0.2(4) . . . . ?
C11B N2B C10B C9B 179.7(2) . . . . ?
C11B N3B C1B N1B -176.6(2) . . . . ?
C11B N3B C1B C2B 3.2(4) . . . . ?
C12B N3B C1B N1B 5.5(4) . . . . ?
C12B N3B C1B C2B -174.7(2) . . . . ?
C12B N3B C11B N2B -4.3(3) . . . . ?
C12B N3B C11B C4B 175.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.857
####################################################################### 
# 
# 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_3f-OTf
_database_code_depnum_ccdc_archive 'CCDC 1536800'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_audit_creation_date             2017-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H14 N5 S, C F3 O3 S'
_chemical_formula_sum            'C15 H14 F3 N5 O3 S2'
_chemical_formula_weight         433.43
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1521(15)
_cell_length_b                   11.658(2)
_cell_length_c                   13.584(2)
_cell_angle_alpha                69.289(16)
_cell_angle_beta                 79.357(16)
_cell_angle_gamma                85.084(18)
_cell_volume                     895.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1661
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      28.6930
_cell_measurement_theta_min      3.2470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -4 13 0.0455
3 3 -14 0.0420
0 -6 -19 0.0482
-7 8 4 0.0441
7 -8 -3 0.0311
-6 -13 -7 0.0787
5 14 9 0.0464
-7 9 0 0.0331

_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.073
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5516
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.869
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  88.00   2.00   59.25    --   19.23  57.00 120.00   43
  2  ω    -11.00  87.00   2.00   59.25    --   19.23  77.00-120.00   49
  3  ω     22.00  60.00   2.00   59.25    --   19.23 -99.00   0.00   19
  4  ω    -22.00  88.00   2.00   59.25    --   19.23  19.00  60.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2434
_reflns_number_total             3497
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.397
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.118
_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)+(0.0524P)²+0.3998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1555
_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. Restrained distances
 N5-H5A
 0.81 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F2A \\sim F3A \\sim F1A: within 2.5A with sigma of 0.01 and sigma for terminal
atoms of 0.01
F1B \\sim F3B \\sim F2B: within 2.5A with sigma of 0.01 and sigma for terminal
atoms of 0.01
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12)
5.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.18870(17) 0.21253(10) 0.24667(8) 0.0337(3) Uani 1 1 d . . . . .
N1 N 0.2116(6) 0.4545(3) 0.4001(3) 0.0305(8) Uani 1 1 d . . . . .
H1A H 0.232(6) 0.523(4) 0.410(3) 0.034(11) Uiso 1 1 d . . . . .
H1B H 0.304(7) 0.387(4) 0.430(3) 0.041(12) Uiso 1 1 d . . . . .
N2 N 0.0260(5) 0.3508(3) 0.3242(2) 0.0238(7) Uani 1 1 d . . . . .
N3 N 0.1999(5) 0.2805(3) 0.1182(2) 0.0250(7) Uani 1 1 d . . . . .
N4 N 0.1799(5) 0.1085(3) 0.0173(2) 0.0275(7) Uani 1 1 d . . . . .
N5 N -0.1499(6) 0.0406(4) 0.1265(3) 0.0375(9) Uani 1 1 d D . . . .
H5A H -0.229(6) 0.038(4) 0.180(2) 0.033(12) Uiso 1 1 d D . . . .
H5B H -0.149(8) -0.002(4) 0.092(4) 0.050(14) Uiso 1 1 d . . . . .
C1 C 0.0507(6) 0.4523(3) 0.3485(3) 0.0242(8) Uani 1 1 d . . . . .
C2 C -0.0962(6) 0.5535(3) 0.3183(3) 0.0282(9) Uani 1 1 d . . . . .
H2 H -0.0843 0.6231 0.3377 0.034 Uiso 1 1 calc R . . . .
C3 C -0.2537(6) 0.5515(3) 0.2617(3) 0.0299(9) Uani 1 1 d . . . . .
H3 H -0.3519 0.6199 0.2409 0.036 Uiso 1 1 calc R . . . .
C4 C -0.2724(6) 0.4482(4) 0.2335(3) 0.0298(9) Uani 1 1 d . . . . .
H4 H -0.3803 0.4477 0.1919 0.036 Uiso 1 1 calc R . . . .
C5 C -0.1360(6) 0.3490(4) 0.2660(3) 0.0282(9) Uani 1 1 d . . . . .
C6 C 0.0360(6) 0.2066(3) 0.1450(3) 0.0279(9) Uani 1 1 d . . . . .
C7 C 0.0228(6) 0.1156(3) 0.0948(3) 0.0268(8) Uani 1 1 d . . . . .
C8 C 0.3572(6) 0.1839(3) -0.0114(3) 0.0239(8) Uani 1 1 d . . . . .
C9 C 0.5339(6) 0.1743(4) -0.0909(3) 0.0306(9) Uani 1 1 d . . . . .
H9 H 0.5279 0.1169 -0.1255 0.037 Uiso 1 1 calc R . . . .
C10 C 0.7139(7) 0.2472(4) -0.1182(3) 0.0356(10) Uani 1 1 d . . . . .
H10 H 0.8327 0.2397 -0.1714 0.043 Uiso 1 1 calc R . . . .
C11 C 0.7246(7) 0.3333(4) -0.0682(3) 0.0358(10) Uani 1 1 d . . . . .
H11 H 0.8496 0.3841 -0.0882 0.043 Uiso 1 1 calc R . . . .
C12 C 0.5569(7) 0.3439(3) 0.0083(3) 0.0317(9) Uani 1 1 d . . . . .
H12 H 0.5656 0.4020 0.0418 0.038 Uiso 1 1 calc R . . . .
C13 C 0.3695(6) 0.2699(3) 0.0389(3) 0.0244(8) Uani 1 1 d . . . . .
C14 C 0.1739(6) 0.2448(3) 0.3620(3) 0.0319(9) Uani 1 1 d . . . . .
H14A H 0.3231 0.2632 0.3209 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.1192 0.1734 0.3528 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.1783 0.2270 0.4378 0.048 Uiso 1 1 calc GR . . . .
S2 S 0.57672(18) 0.23308(9) 0.58875(8) 0.0324(3) Uani 1 1 d . . . . .
F1A F 0.896(3) 0.0786(18) 0.5752(17) 0.066(4) Uani 0.47(4) 1 d . U P A 1
F1B F 0.862(3) 0.0650(14) 0.5511(12) 0.066(4) Uani 0.53(4) 1 d . U P A 2
F2A F 0.581(3) 0.0122(12) 0.5808(15) 0.059(3) Uani 0.47(4) 1 d . U P A 1
F2B F 0.5312(19) 0.0055(10) 0.6228(17) 0.076(3) Uani 0.53(4) 1 d . U P A 2
F3A F 0.666(3) 0.0167(12) 0.7227(12) 0.053(3) Uani 0.47(4) 1 d . U P A 1
F3B F 0.745(3) 0.0391(16) 0.7155(12) 0.067(3) Uani 0.53(4) 1 d . U P A 2
O1 O 0.5530(5) 0.2701(3) 0.4793(2) 0.0456(8) Uani 1 1 d . . . . .
O2 O 0.7419(7) 0.2967(3) 0.6078(3) 0.0780(12) Uani 1 1 d . . . . .
O3 O 0.3733(6) 0.2163(4) 0.6623(3) 0.0727(12) Uani 1 1 d . . . . .
C15 C 0.6880(8) 0.0783(4) 0.6192(3) 0.0401(11) 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 C5 1.767(4) . ?
S1 C6 1.780(4) . ?
N1 H1A 0.88(4) . ?
N1 H1B 0.94(5) . ?
N1 C1 1.322(5) . ?
N2 C1 1.363(4) . ?
N2 C5 1.388(5) . ?
N2 C14 1.466(5) . ?
N3 C6 1.297(4) . ?
N3 C13 1.387(4) . ?
N4 C7 1.312(4) . ?
N4 C8 1.371(5) . ?
N5 H5A 0.794(19) . ?
N5 H5B 0.79(5) . ?
N5 C7 1.343(5) . ?
C1 C2 1.410(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.350(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.358(5) . ?
C6 C7 1.464(5) . ?
C8 C9 1.411(5) . ?
C8 C13 1.412(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.369(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.409(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.354(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.409(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S2 O1 1.427(3) . ?
S2 O2 1.418(3) . ?
S2 O3 1.430(3) . ?
S2 C15 1.806(4) . ?
F1A C15 1.309(18) . ?
F1B C15 1.315(16) . ?
F2A C15 1.340(13) . ?
F2B C15 1.322(12) . ?
F3A C15 1.320(16) . ?
F3B C15 1.327(15) . ?

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
C5 S1 C6 101.67(17) . . ?
H1A N1 H1B 117(4) . . ?
C1 N1 H1A 118(3) . . ?
C1 N1 H1B 125(3) . . ?
C1 N2 C5 120.3(3) . . ?
C1 N2 C14 118.0(3) . . ?
C5 N2 C14 121.7(3) . . ?
C6 N3 C13 117.1(3) . . ?
C7 N4 C8 118.5(3) . . ?
H5A N5 H5B 128(4) . . ?
C7 N5 H5A 117(3) . . ?
C7 N5 H5B 114(3) . . ?
N1 C1 N2 119.6(4) . . ?
N1 C1 C2 120.9(3) . . ?
N2 C1 C2 119.5(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
N2 C5 S1 120.4(3) . . ?
C4 C5 S1 119.0(3) . . ?
C4 C5 N2 120.2(3) . . ?
N3 C6 S1 120.4(3) . . ?
N3 C6 C7 123.2(3) . . ?
C7 C6 S1 116.4(3) . . ?
N4 C7 N5 119.8(3) . . ?
N4 C7 C6 119.6(3) . . ?
N5 C7 C6 120.6(3) . . ?
N4 C8 C9 119.9(3) . . ?
N4 C8 C13 121.2(3) . . ?
C9 C8 C13 118.9(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
N3 C13 C8 120.3(3) . . ?
N3 C13 C12 120.4(3) . . ?
C12 C13 C8 119.3(3) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 S2 O3 114.9(2) . . ?
O1 S2 C15 104.22(19) . . ?
O2 S2 O1 113.9(2) . . ?
O2 S2 O3 115.8(3) . . ?
O2 S2 C15 103.4(2) . . ?
O3 S2 C15 102.2(2) . . ?
F1A C15 S2 110.6(9) . . ?
F1A C15 F2A 106.8(8) . . ?
F1A C15 F3A 110.0(9) . . ?
F1B C15 S2 114.6(7) . . ?
F1B C15 F2B 108.7(8) . . ?
F1B C15 F3B 107.8(8) . . ?
F2A C15 S2 111.4(6) . . ?
F2B C15 S2 108.8(6) . . ?
F2B C15 F3B 106.8(7) . . ?
F3A C15 S2 113.0(7) . . ?
F3A C15 F2A 104.8(8) . . ?
F3B C15 S2 110.0(7) . . ?

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
N1 H1A O2 0.88(4) 2.04(4) 2.901(5) 164(4) 2_666
N1 H1B O1 0.94(5) 2.01(5) 2.935(5) 167(3) .
N5 H5B N4 0.79(5) 2.29(5) 3.076(5) 173(5) 2

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 C6 C7 N4 178.2(3) . . . . ?
S1 C6 C7 N5 -1.0(5) . . . . ?
N1 C1 C2 C3 177.2(3) . . . . ?
N2 C1 C2 C3 -2.9(5) . . . . ?
N3 C6 C7 N4 -1.5(6) . . . . ?
N3 C6 C7 N5 179.3(4) . . . . ?
N4 C8 C9 C10 -178.5(4) . . . . ?
N4 C8 C13 N3 -0.6(5) . . . . ?
N4 C8 C13 C12 178.8(3) . . . . ?
C1 N2 C5 S1 -173.1(2) . . . . ?
C1 N2 C5 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C5 1.9(5) . . . . ?
C3 C4 C5 S1 170.8(3) . . . . ?
C3 C4 C5 N2 -1.8(5) . . . . ?
C5 S1 C6 N3 10.6(4) . . . . ?
C5 S1 C6 C7 -169.1(3) . . . . ?
C5 N2 C1 N1 -177.2(3) . . . . ?
C5 N2 C1 C2 3.0(5) . . . . ?
C6 S1 C5 N2 -77.5(3) . . . . ?
C6 S1 C5 C4 109.9(3) . . . . ?
C6 N3 C13 C8 1.7(5) . . . . ?
C6 N3 C13 C12 -177.7(4) . . . . ?
C7 N4 C8 C9 177.0(3) . . . . ?
C7 N4 C8 C13 -1.6(5) . . . . ?
C8 N4 C7 N5 -178.2(4) . . . . ?
C8 N4 C7 C6 2.6(5) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
C9 C8 C13 N3 -179.2(3) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 N3 179.2(4) . . . . ?
C11 C12 C13 C8 -0.1(6) . . . . ?
C13 N3 C6 S1 179.6(3) . . . . ?
C13 N3 C6 C7 -0.7(6) . . . . ?
C13 C8 C9 C10 0.1(6) . . . . ?
C14 N2 C1 N1 3.2(5) . . . . ?
C14 N2 C1 C2 -176.7(3) . . . . ?
C14 N2 C5 S1 6.5(4) . . . . ?
C14 N2 C5 C4 179.0(3) . . . . ?
O1 S2 C15 F1A 73.4(12) . . . . ?
O1 S2 C15 F1B 50.2(11) . . . . ?
O1 S2 C15 F2A -45.1(11) . . . . ?
O1 S2 C15 F2B -71.7(11) . . . . ?
O1 S2 C15 F3A -162.8(10) . . . . ?
O1 S2 C15 F3B 171.7(11) . . . . ?
O2 S2 C15 F1A -46.0(12) . . . . ?
O2 S2 C15 F1B -69.2(11) . . . . ?
O2 S2 C15 F2A -164.6(11) . . . . ?
O2 S2 C15 F2B 168.9(11) . . . . ?
O2 S2 C15 F3A 77.8(11) . . . . ?
O2 S2 C15 F3B 52.3(11) . . . . ?
O3 S2 C15 F1A -166.6(11) . . . . ?
O3 S2 C15 F1B 170.2(11) . . . . ?
O3 S2 C15 F2A 74.8(11) . . . . ?
O3 S2 C15 F2B 48.3(11) . . . . ?
O3 S2 C15 F3A -42.8(11) . . . . ?
O3 S2 C15 F3B -68.3(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
