# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_TS791
_database_code_depnum_ccdc_archive 'CCDC 897056'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H14 N2 O2 S2'
_chemical_formula_sum            'C12 H14 N2 O2 S2'
_chemical_formula_weight         282.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_int_tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0971(1)
_cell_length_b                   12.4447(2)
_cell_length_c                   13.3768(3)
_cell_angle_alpha                87.181(2)
_cell_angle_beta                 80.232(1)
_cell_angle_gamma                88.150(1)
_cell_volume                     1326.39(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    36860
_cell_measurement_theta_min      3.6802
_cell_measurement_theta_max      45.6474

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            92204
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         45.74
_reflns_number_total             22625
_reflns_number_gt                15703
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         22625
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.179912(16) 0.775207(11) 0.458098(10) 0.01349(2) Uani 1 1 d . . .
S2A S 0.720125(19) 0.843921(14) 0.426226(13) 0.02187(3) Uani 1 1 d . . .
O1A O 0.14856(6) 0.85349(4) 0.37966(4) 0.01928(8) Uani 1 1 d . . .
O2A O 0.07136(6) 0.77535(4) 0.55517(4) 0.02112(8) Uani 1 1 d . . .
N1A N 0.42296(8) 0.71963(6) 0.65876(5) 0.02886(12) Uani 1 1 d . . .
N2A N 0.50158(6) 0.82773(4) 0.30489(4) 0.01654(8) Uani 1 1 d . . .
H2A H 0.4117(13) 0.8192(8) 0.2882(8) 0.026(2) Uiso 1 1 d . . .
C1A C 0.38469(7) 0.79066(5) 0.48006(4) 0.01464(8) Uani 1 1 d . . .
C2A C 0.51686(6) 0.82030(4) 0.40263(4) 0.01424(8) Uani 1 1 d . . .
C3A C 0.40897(8) 0.75299(5) 0.57821(5) 0.01919(10) Uani 1 1 d . . .
C4A C 0.69265(10) 0.89943(6) 0.55046(6) 0.02667(13) Uani 1 1 d . . .
H4AA H 0.7874(15) 0.9396(9) 0.5474(9) 0.037(3) Uiso 1 1 d . . .
H4AB H 0.5917(17) 0.9427(11) 0.5623(10) 0.048(3) Uiso 1 1 d . . .
H4AC H 0.6961(14) 0.8439(10) 0.6020(9) 0.037(3) Uiso 1 1 d . . .
C5A C 0.17527(7) 0.64628(4) 0.40939(4) 0.01441(8) Uani 1 1 d . . .
C6A C 0.12705(8) 0.63543(5) 0.31577(5) 0.01882(9) Uani 1 1 d . . .
H6A H 0.0953(16) 0.6949(10) 0.2801(10) 0.044(3) Uiso 1 1 d . . .
C7A C 0.11986(9) 0.53244(6) 0.28021(6) 0.02490(12) Uani 1 1 d . . .
H7A H 0.0899(15) 0.5269(10) 0.2109(9) 0.038(3) Uiso 1 1 d . . .
C8A C 0.15904(9) 0.44332(6) 0.33817(6) 0.02642(13) Uani 1 1 d . . .
H8A H 0.1540(15) 0.3735(10) 0.3140(9) 0.040(3) Uiso 1 1 d . . .
C9A C 0.20767(10) 0.45494(6) 0.43193(6) 0.02694(13) Uani 1 1 d . . .
H9A H 0.2320(15) 0.3953(10) 0.4713(9) 0.037(3) Uiso 1 1 d . . .
C10A C 0.21637(9) 0.55674(5) 0.46809(5) 0.02225(11) Uani 1 1 d . . .
H10A H 0.2515(14) 0.5647(9) 0.5369(8) 0.032(3) Uiso 1 1 d . . .
C11A C 0.62482(8) 0.86965(5) 0.21989(5) 0.01895(10) Uani 1 1 d . . .
H11A H 0.7365(13) 0.8556(8) 0.2347(8) 0.023(2) Uiso 1 1 d . . .
H11B H 0.6207(13) 0.8264(8) 0.1596(8) 0.026(2) Uiso 1 1 d . . .
C12A C 0.59417(10) 0.98821(6) 0.19727(6) 0.02824(14) Uani 1 1 d . . .
H12A H 0.6785(16) 1.0149(10) 0.1408(10) 0.041(3) Uiso 1 1 d . . .
H12B H 0.482(2) 0.9970(12) 0.1769(11) 0.062(4) Uiso 1 1 d . . .
H12C H 0.6060(17) 1.0299(11) 0.2547(10) 0.049(3) Uiso 1 1 d . . .
S1B S 0.979876(15) 0.329327(10) 0.020968(10) 0.01208(2) Uani 1 1 d . . .
S2B S 0.435040(17) 0.379953(12) 0.089625(12) 0.01805(3) Uani 1 1 d . . .
O1B O 1.02109(5) 0.41278(3) 0.08349(4) 0.01755(7) Uani 1 1 d . . .
O2B O 1.07173(5) 0.32260(4) -0.08113(3) 0.01754(7) Uani 1 1 d . . .
N1B N 0.67924(7) 0.21961(5) -0.11587(4) 0.02087(9) Uani 1 1 d . . .
N2B N 0.69225(6) 0.48579(4) 0.12808(4) 0.01575(8) Uani 1 1 d . . .
H2B H 0.7922(13) 0.5073(8) 0.1111(8) 0.024(2) Uiso 1 1 d . . .
C1B C 0.76708(6) 0.33957(4) 0.01623(4) 0.01307(8) Uani 1 1 d . . .
C2B C 0.65069(6) 0.40384(4) 0.07940(4) 0.01266(7) Uani 1 1 d . . .
C3B C 0.71598(7) 0.27401(4) -0.05559(4) 0.01508(8) Uani 1 1 d . . .
C4B C 0.42992(9) 0.23726(6) 0.12225(6) 0.02350(12) Uani 1 1 d . . .
H4BA H 0.3220(15) 0.2284(9) 0.1510(9) 0.033(3) Uiso 1 1 d . . .
H4BB H 0.4551(16) 0.1951(10) 0.0632(10) 0.045(3) Uiso 1 1 d . . .
H4BC H 0.5094(15) 0.2203(10) 0.1698(9) 0.041(3) Uiso 1 1 d . . .
C5B C 1.01196(6) 0.20508(4) 0.08570(4) 0.01266(7) Uani 1 1 d . . .
C6B C 0.95712(8) 0.19412(5) 0.19027(4) 0.01848(9) Uani 1 1 d . . .
H6B H 0.8927(13) 0.2508(8) 0.2251(8) 0.025(2) Uiso 1 1 d . . .
C7B C 0.99240(9) 0.09798(5) 0.24097(5) 0.02202(11) Uani 1 1 d . . .
H7B H 0.9582(13) 0.0919(8) 0.3148(8) 0.027(2) Uiso 1 1 d . . .
C8B C 1.08166(9) 0.01517(5) 0.18804(5) 0.02071(10) Uani 1 1 d . . .
H8B H 1.1059(12) -0.0508(8) 0.2211(8) 0.022(2) Uiso 1 1 d . . .
C9B C 1.13520(8) 0.02733(5) 0.08407(5) 0.01932(10) Uani 1 1 d . . .
H9B H 1.1994(14) -0.0313(9) 0.0456(8) 0.031(3) Uiso 1 1 d . . .
C10B C 1.09934(7) 0.12228(4) 0.03183(4) 0.01574(8) Uani 1 1 d . . .
H10B H 1.1329(13) 0.1283(8) -0.0415(8) 0.025(2) Uiso 1 1 d . . .
C11B C 0.58277(8) 0.54648(6) 0.20531(6) 0.02505(13) Uani 1 1 d . . .
H11C H 0.5422(15) 0.6116(10) 0.1758(9) 0.041(3) Uiso 1 1 d . . .
H11D H 0.4875(19) 0.5023(12) 0.2353(11) 0.063(4) Uiso 1 1 d . . .
C12B C 0.67360(11) 0.56964(7) 0.29082(6) 0.03019(15) Uani 1 1 d . . .
H12D H 0.5956(16) 0.5963(10) 0.3484(10) 0.046(3) Uiso 1 1 d . . .
H12E H 0.7296(17) 0.5092(11) 0.3137(10) 0.052(4) Uiso 1 1 d . . .
H12F H 0.7764(17) 0.6241(11) 0.2607(10) 0.051(4) Uiso 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
S1A O2A 1.4392(5) . ?
S1A O1A 1.4450(5) . ?
S1A C1A 1.7504(5) . ?
S1A C5A 1.7650(6) . ?
S2A C2A 1.7640(5) . ?
S2A C4A 1.8072(8) . ?
N1A C3A 1.1577(8) . ?
N2A C2A 1.3324(8) . ?
N2A C11A 1.4667(8) . ?
N2A H2A 0.808(11) . ?
C1A C2A 1.4021(8) . ?
C1A C3A 1.4154(8) . ?
C4A H4AA 0.923(12) . ?
C4A H4AB 0.958(14) . ?
C4A H4AC 0.955(12) . ?
C5A C6A 1.3875(8) . ?
C5A C10A 1.3955(8) . ?
C6A C7A 1.3952(9) . ?
C6A H6A 0.914(13) . ?
C7A C8A 1.3813(12) . ?
C7A H7A 1.003(12) . ?
C8A C9A 1.3922(12) . ?
C8A H8A 0.946(13) . ?
C9A C10A 1.3862(10) . ?
C9A H9A 0.925(12) . ?
C10A H10A 1.019(11) . ?
C11A C12A 1.5126(10) . ?
C11A H11A 0.967(10) . ?
C11A H11B 0.998(11) . ?
C12A H12A 0.981(13) . ?
C12A H12B 0.996(16) . ?
C12A H12C 0.967(14) . ?
S1B O2B 1.4450(4) . ?
S1B O1B 1.4464(4) . ?
S1B C1B 1.7353(5) . ?
S1B C5B 1.7683(5) . ?
S2B C2B 1.7620(5) . ?
S2B C4B 1.8077(7) . ?
N1B C3B 1.1598(8) . ?
N2B C2B 1.3188(7) . ?
N2B C11B 1.4651(8) . ?
N2B H2B 0.851(10) . ?
C1B C2B 1.4105(7) . ?
C1B C3B 1.4119(8) . ?
C4B H4BA 0.901(11) . ?
C4B H4BB 0.959(13) . ?
C4B H4BC 0.990(12) . ?
C5B C10B 1.3909(7) . ?
C5B C6B 1.3952(8) . ?
C6B C7B 1.3918(9) . ?
C6B H6B 0.956(10) . ?
C7B C8B 1.3913(10) . ?
C7B H7B 0.979(11) . ?
C8B C9B 1.3871(9) . ?
C8B H8B 0.945(10) . ?
C9B C10B 1.3908(8) . ?
C9B H9B 0.995(11) . ?
C10B H10B 0.972(10) . ?
C11B C12B 1.5047(11) . ?
C11B H11C 0.957(12) . ?
C11B H11D 0.979(16) . ?
C12B H12D 0.975(13) . ?
C12B H12E 0.932(14) . ?
C12B H12F 1.100(14) . ?

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
O2A S1A O1A 118.82(3) . . ?
O2A S1A C1A 107.25(3) . . ?
O1A S1A C1A 108.32(3) . . ?
O2A S1A C5A 107.98(3) . . ?
O1A S1A C5A 107.61(3) . . ?
C1A S1A C5A 106.22(3) . . ?
C2A S2A C4A 106.08(3) . . ?
C2A N2A C11A 127.00(5) . . ?
C2A N2A H2A 120.2(7) . . ?
C11A N2A H2A 111.8(7) . . ?
C2A C1A C3A 123.14(5) . . ?
C2A C1A S1A 122.68(4) . . ?
C3A C1A S1A 113.36(4) . . ?
N2A C2A C1A 122.85(5) . . ?
N2A C2A S2A 114.50(4) . . ?
C1A C2A S2A 122.57(4) . . ?
N1A C3A C1A 177.15(7) . . ?
S2A C4A H4AA 103.1(7) . . ?
S2A C4A H4AB 110.6(8) . . ?
H4AA C4A H4AB 112.2(11) . . ?
S2A C4A H4AC 111.0(7) . . ?
H4AA C4A H4AC 107.2(10) . . ?
H4AB C4A H4AC 112.4(11) . . ?
C6A C5A C10A 121.42(6) . . ?
C6A C5A S1A 119.94(4) . . ?
C10A C5A S1A 118.62(5) . . ?
C5A C6A C7A 118.85(6) . . ?
C5A C6A H6A 120.0(8) . . ?
C7A C6A H6A 121.1(8) . . ?
C8A C7A C6A 120.11(6) . . ?
C8A C7A H7A 122.5(7) . . ?
C6A C7A H7A 117.3(7) . . ?
C7A C8A C9A 120.67(6) . . ?
C7A C8A H8A 120.0(7) . . ?
C9A C8A H8A 119.3(7) . . ?
C10A C9A C8A 119.92(7) . . ?
C10A C9A H9A 119.3(7) . . ?
C8A C9A H9A 120.7(7) . . ?
C9A C10A C5A 119.02(6) . . ?
C9A C10A H10A 119.5(6) . . ?
C5A C10A H10A 121.5(6) . . ?
N2A C11A C12A 111.57(5) . . ?
N2A C11A H11A 109.3(6) . . ?
C12A C11A H11A 111.5(6) . . ?
N2A C11A H11B 108.5(6) . . ?
C12A C11A H11B 111.6(6) . . ?
H11A C11A H11B 104.1(8) . . ?
C11A C12A H12A 110.3(7) . . ?
C11A C12A H12B 107.9(9) . . ?
H12A C12A H12B 108.5(11) . . ?
C11A C12A H12C 110.9(8) . . ?
H12A C12A H12C 105.9(11) . . ?
H12B C12A H12C 113.3(12) . . ?
O2B S1B O1B 118.65(3) . . ?
O2B S1B C1B 108.97(3) . . ?
O1B S1B C1B 108.54(3) . . ?
O2B S1B C5B 107.03(3) . . ?
O1B S1B C5B 106.73(3) . . ?
C1B S1B C5B 106.24(2) . . ?
C2B S2B C4B 101.07(3) . . ?
C2B N2B C11B 126.93(5) . . ?
C2B N2B H2B 116.5(7) . . ?
C11B N2B H2B 116.6(7) . . ?
C2B C1B C3B 121.41(5) . . ?
C2B C1B S1B 124.59(4) . . ?
C3B C1B S1B 113.97(4) . . ?
N2B C2B C1B 123.94(5) . . ?
N2B C2B S2B 116.87(4) . . ?
C1B C2B S2B 119.08(4) . . ?
N1B C3B C1B 177.86(6) . . ?
S2B C4B H4BA 102.3(7) . . ?
S2B C4B H4BB 111.9(7) . . ?
H4BA C4B H4BB 109.3(11) . . ?
S2B C4B H4BC 108.7(7) . . ?
H4BA C4B H4BC 113.1(10) . . ?
H4BB C4B H4BC 111.3(10) . . ?
C10B C5B C6B 121.50(5) . . ?
C10B C5B S1B 118.99(4) . . ?
C6B C5B S1B 119.42(4) . . ?
C7B C6B C5B 118.64(6) . . ?
C7B C6B H6B 121.3(6) . . ?
C5B C6B H6B 120.0(6) . . ?
C8B C7B C6B 120.34(6) . . ?
C8B C7B H7B 121.3(6) . . ?
C6B C7B H7B 118.3(6) . . ?
C9B C8B C7B 120.30(5) . . ?
C9B C8B H8B 118.2(6) . . ?
C7B C8B H8B 121.5(6) . . ?
C8B C9B C10B 120.23(6) . . ?
C8B C9B H9B 120.9(6) . . ?
C10B C9B H9B 118.9(6) . . ?
C9B C10B C5B 118.99(5) . . ?
C9B C10B H10B 119.3(6) . . ?
C5B C10B H10B 121.7(6) . . ?
N2B C11B C12B 110.47(5) . . ?
N2B C11B H11C 110.6(7) . . ?
C12B C11B H11C 111.0(7) . . ?
N2B C11B H11D 109.2(9) . . ?
C12B C11B H11D 106.2(9) . . ?
H11C C11B H11D 109.2(11) . . ?
C11B C12B H12D 110.7(8) . . ?
C11B C12B H12E 112.7(9) . . ?
H12D C12B H12E 107.8(11) . . ?
C11B C12B H12F 108.1(7) . . ?
H12D C12B H12F 114.5(10) . . ?
H12E C12B H12F 102.9(11) . . ?

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
O2A S1A C1A C2A -163.88(5) . . . . ?
O1A S1A C1A C2A -34.50(6) . . . . ?
C5A S1A C1A C2A 80.84(5) . . . . ?
O2A S1A C1A C3A 26.25(5) . . . . ?
O1A S1A C1A C3A 155.63(5) . . . . ?
C5A S1A C1A C3A -89.02(5) . . . . ?
C11A N2A C2A C1A 172.41(6) . . . . ?
C11A N2A C2A S2A -10.76(8) . . . . ?
C3A C1A C2A N2A 161.43(6) . . . . ?
S1A C1A C2A N2A -7.45(8) . . . . ?
C3A C1A C2A S2A -15.15(8) . . . . ?
S1A C1A C2A S2A 175.97(3) . . . . ?
C4A S2A C2A N2A 150.39(5) . . . . ?
C4A S2A C2A C1A -32.77(6) . . . . ?
C2A C1A C3A N1A -149.6(15) . . . . ?
S1A C1A C3A N1A 20.2(16) . . . . ?
O2A S1A C5A C6A 122.31(5) . . . . ?
O1A S1A C5A C6A -7.08(5) . . . . ?
C1A S1A C5A C6A -122.91(5) . . . . ?
O2A S1A C5A C10A -55.96(5) . . . . ?
O1A S1A C5A C10A 174.65(5) . . . . ?
C1A S1A C5A C10A 58.82(5) . . . . ?
C10A C5A C6A C7A 0.00(9) . . . . ?
S1A C5A C6A C7A -178.22(5) . . . . ?
C5A C6A C7A C8A 0.51(10) . . . . ?
C6A C7A C8A C9A -0.66(10) . . . . ?
C7A C8A C9A C10A 0.29(11) . . . . ?
C8A C9A C10A C5A 0.22(11) . . . . ?
C6A C5A C10A C9A -0.37(10) . . . . ?
S1A C5A C10A C9A 177.88(5) . . . . ?
C2A N2A C11A C12A -92.88(8) . . . . ?
O2B S1B C1B C2B -142.35(5) . . . . ?
O1B S1B C1B C2B -11.81(6) . . . . ?
C5B S1B C1B C2B 102.64(5) . . . . ?
O2B S1B C1B C3B 39.68(5) . . . . ?
O1B S1B C1B C3B 170.22(4) . . . . ?
C5B S1B C1B C3B -75.33(4) . . . . ?
C11B N2B C2B C1B -170.91(6) . . . . ?
C11B N2B C2B S2B 12.82(8) . . . . ?
C3B C1B C2B N2B -161.80(5) . . . . ?
S1B C1B C2B N2B 20.38(8) . . . . ?
C3B C1B C2B S2B 14.39(7) . . . . ?
S1B C1B C2B S2B -163.43(3) . . . . ?
C4B S2B C2B N2B -131.00(5) . . . . ?
C4B S2B C2B C1B 52.54(5) . . . . ?
C2B C1B C3B N1B 169.5(16) . . . . ?
S1B C1B C3B N1B -12.5(16) . . . . ?
O2B S1B C5B C10B -5.64(5) . . . . ?
O1B S1B C5B C10B -133.64(4) . . . . ?
C1B S1B C5B C10B 110.67(5) . . . . ?
O2B S1B C5B C6B 171.00(5) . . . . ?
O1B S1B C5B C6B 43.00(5) . . . . ?
C1B S1B C5B C6B -72.69(5) . . . . ?
C10B C5B C6B C7B 0.40(9) . . . . ?
S1B C5B C6B C7B -176.15(5) . . . . ?
C5B C6B C7B C8B 0.46(10) . . . . ?
C6B C7B C8B C9B -0.51(10) . . . . ?
C7B C8B C9B C10B -0.31(10) . . . . ?
C8B C9B C10B C5B 1.15(9) . . . . ?
C6B C5B C10B C9B -1.21(9) . . . . ?
S1B C5B C10B C9B 175.36(4) . . . . ?
C2B N2B C11B C12B 138.31(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
N2A H2A O1A 0.808(11) 2.308(11) 2.8768(7) 128.1(10) .
N2A H2A N1B 0.808(11) 2.608(11) 3.2160(7) 133.3(9) 2_665
N2B H2B O1B 0.851(10) 2.150(10) 2.7621(6) 128.6(9) .
N2B H2B O2B 0.851(10) 2.403(10) 3.0777(7) 136.7(9) 2_765

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        45.74
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_TS794
_database_code_depnum_ccdc_archive 'CCDC 897057'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O2 S2'
_chemical_formula_sum            'C17 H16 N2 O2 S2'
_chemical_formula_weight         344.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_int_tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4275(2)
_cell_length_b                   16.8324(4)
_cell_length_c                   11.6886(2)
_cell_angle_alpha                90.0
_cell_angle_beta                 97.869(2)
_cell_angle_gamma                90.0
_cell_volume                     1642.47(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14050
_cell_measurement_theta_min      3.5123
_cell_measurement_theta_max      40.8981

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            77724
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         41.03
_reflns_number_total             10664
_reflns_number_gt                5529
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0295P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10664
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61721(3) 0.126278(14) 0.549772(19) 0.02346(5) Uani 1 1 d . . .
S2 S 0.10763(3) 0.099509(14) 0.445941(19) 0.02348(5) Uani 1 1 d . . .
O1 O 0.67594(8) 0.10403(4) 0.44384(6) 0.03080(15) Uani 1 1 d . . .
O2 O 0.69586(9) 0.09530(4) 0.65739(6) 0.03508(17) Uani 1 1 d . . .
N1 N 0.32284(14) 0.07600(7) 0.73490(8) 0.0491(3) Uani 1 1 d . . .
N2 N 0.36455(10) 0.09414(5) 0.33052(6) 0.02268(15) Uani 1 1 d . . .
H2 H 0.4633(17) 0.0840(7) 0.3322(10) 0.043(4) Uiso 1 1 d . . .
C1 C 0.41564(11) 0.10024(5) 0.53777(7) 0.02275(17) Uani 1 1 d . . .
C2 C 0.31173(11) 0.09740(5) 0.43326(7) 0.02027(16) Uani 1 1 d . . .
C3 C 0.36011(13) 0.08755(6) 0.64547(8) 0.0310(2) Uani 1 1 d . . .
C4 C 0.01135(12) 0.03658(6) 0.33181(8) 0.02430(18) Uani 1 1 d . . .
H4A H -0.0876(14) 0.0239(6) 0.3583(9) 0.033(3) Uiso 1 1 d . . .
H4B H -0.0087(13) 0.0638(6) 0.2597(9) 0.025(3) Uiso 1 1 d . . .
H4C H 0.0784(14) -0.0115(6) 0.3258(9) 0.036(3) Uiso 1 1 d . . .
C5 C 0.62234(10) 0.23073(5) 0.55945(7) 0.01986(16) Uani 1 1 d . . .
C6 C 0.56152(12) 0.27625(6) 0.46445(8) 0.0278(2) Uani 1 1 d . . .
H6 H 0.5185(14) 0.2513(6) 0.3946(10) 0.037(3) Uiso 1 1 d . . .
C7 C 0.56183(14) 0.35800(6) 0.47414(11) 0.0363(2) Uani 1 1 d . . .
H7 H 0.5236(16) 0.3885(7) 0.4116(11) 0.050(4) Uiso 1 1 d . . .
C8 C 0.62441(13) 0.39330(7) 0.57699(11) 0.0381(3) Uani 1 1 d . . .
H8 H 0.6285(15) 0.4478(8) 0.5850(10) 0.049(4) Uiso 1 1 d . . .
C9 C 0.68508(13) 0.34813(7) 0.67082(10) 0.0359(2) Uani 1 1 d . . .
H9 H 0.7317(16) 0.3688(7) 0.7426(11) 0.047(3) Uiso 1 1 d . . .
C10 C 0.68364(11) 0.26576(6) 0.66353(8) 0.02625(19) Uani 1 1 d . . .
H10 H 0.7267(14) 0.2320(6) 0.7266(9) 0.031(3) Uiso 1 1 d . . .
C11 C 0.27379(10) 0.11217(5) 0.22077(7) 0.02131(17) Uani 1 1 d . . .
C12 C 0.25739(11) 0.05496(6) 0.13453(8) 0.02449(18) Uani 1 1 d . . .
H12 H 0.3044(14) 0.0052(6) 0.1488(9) 0.029(3) Uiso 1 1 d . . .
C13 C 0.16782(12) 0.07223(6) 0.02886(8) 0.02741(19) Uani 1 1 d . . .
H13 H 0.1566(13) 0.0330(7) -0.0297(9) 0.034(3) Uiso 1 1 d . . .
C14 C 0.09314(12) 0.14540(6) 0.00774(8) 0.0278(2) Uani 1 1 d . . .
C15 C 0.11287(13) 0.20198(6) 0.09516(9) 0.0288(2) Uani 1 1 d . . .
H15 H 0.0615(14) 0.2505(6) 0.0819(9) 0.032(3) Uiso 1 1 d . . .
C16 C 0.20440(12) 0.18613(6) 0.20129(8) 0.02553(18) Uani 1 1 d . . .
H16 H 0.2163(12) 0.2240(6) 0.2598(8) 0.022(3) Uiso 1 1 d . . .
C17 C -0.00605(15) 0.16235(8) -0.10655(10) 0.0392(3) Uani 1 1 d . . .
H17A H 0.0489(19) 0.1484(9) -0.1656(13) 0.067(5) Uiso 1 1 d . . .
H17B H -0.1064(19) 0.1347(8) -0.1202(12) 0.061(4) Uiso 1 1 d . . .
H17C H -0.0313(17) 0.2182(9) -0.1141(12) 0.060(4) Uiso 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 O2 1.4371(7) . ?
S1 O1 1.4444(7) . ?
S1 C1 1.7413(10) . ?
S1 C5 1.7620(9) . ?
S2 C2 1.7469(9) . ?
S2 C4 1.8065(10) . ?
N1 C3 1.1485(12) . ?
N2 C2 1.3377(11) . ?
N2 C11 1.4333(11) . ?
N2 H2 0.847(14) . ?
C1 C2 1.4030(12) . ?
C1 C3 1.4180(13) . ?
C4 H4A 0.953(12) . ?
C4 H4B 0.953(11) . ?
C4 H4C 0.995(11) . ?
C5 C10 1.3866(12) . ?
C5 C6 1.3881(12) . ?
C6 C7 1.3807(14) . ?
C6 H6 0.945(11) . ?
C7 C8 1.3795(17) . ?
C7 H7 0.916(13) . ?
C8 C9 1.3744(17) . ?
C8 H8 0.923(13) . ?
C9 C10 1.3890(15) . ?
C9 H9 0.943(13) . ?
C10 H10 0.962(11) . ?
C11 C16 1.3811(13) . ?
C11 C12 1.3873(12) . ?
C12 C13 1.3873(13) . ?
C12 H12 0.932(11) . ?
C13 C14 1.3897(15) . ?
C13 H13 0.946(11) . ?
C14 C15 1.3901(15) . ?
C14 C17 1.5030(14) . ?
C15 C16 1.3939(14) . ?
C15 H15 0.927(11) . ?
C16 H16 0.930(10) . ?
C17 H17A 0.913(15) . ?
C17 H17B 0.960(16) . ?
C17 H17C 0.966(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
O2 S1 O1 119.03(4) . . ?
O2 S1 C1 107.89(4) . . ?
O1 S1 C1 108.10(4) . . ?
O2 S1 C5 107.55(4) . . ?
O1 S1 C5 107.78(4) . . ?
C1 S1 C5 105.75(4) . . ?
C2 S2 C4 105.86(4) . . ?
C2 N2 C11 126.33(8) . . ?
C2 N2 H2 115.8(8) . . ?
C11 N2 H2 117.7(8) . . ?
C2 C1 C3 121.69(9) . . ?
C2 C1 S1 124.36(7) . . ?
C3 C1 S1 113.79(7) . . ?
N2 C2 C1 122.56(8) . . ?
N2 C2 S2 121.97(7) . . ?
C1 C2 S2 115.46(6) . . ?
N1 C3 C1 176.52(13) . . ?
S2 C4 H4A 102.5(6) . . ?
S2 C4 H4B 112.2(6) . . ?
H4A C4 H4B 109.7(9) . . ?
S2 C4 H4C 109.1(7) . . ?
H4A C4 H4C 111.8(9) . . ?
H4B C4 H4C 111.2(9) . . ?
C10 C5 C6 121.31(9) . . ?
C10 C5 S1 118.91(7) . . ?
C6 C5 S1 119.76(7) . . ?
C7 C6 C5 119.22(9) . . ?
C7 C6 H6 120.6(7) . . ?
C5 C6 H6 120.1(7) . . ?
C8 C7 C6 119.80(11) . . ?
C8 C7 H7 120.3(8) . . ?
C6 C7 H7 119.8(8) . . ?
C9 C8 C7 120.88(10) . . ?
C9 C8 H8 117.7(8) . . ?
C7 C8 H8 121.4(8) . . ?
C8 C9 C10 120.28(10) . . ?
C8 C9 H9 124.8(8) . . ?
C10 C9 H9 114.9(8) . . ?
C5 C10 C9 118.51(10) . . ?
C5 C10 H10 118.5(6) . . ?
C9 C10 H10 123.0(6) . . ?
C16 C11 C12 120.55(8) . . ?
C16 C11 N2 120.03(8) . . ?
C12 C11 N2 119.42(8) . . ?
C11 C12 C13 119.29(9) . . ?
C11 C12 H12 119.8(7) . . ?
C13 C12 H12 120.9(7) . . ?
C12 C13 C14 121.47(9) . . ?
C12 C13 H13 119.1(7) . . ?
C14 C13 H13 119.4(7) . . ?
C13 C14 C15 118.09(9) . . ?
C13 C14 C17 120.63(10) . . ?
C15 C14 C17 121.28(10) . . ?
C14 C15 C16 121.26(9) . . ?
C14 C15 H15 118.3(7) . . ?
C16 C15 H15 120.4(7) . . ?
C11 C16 C15 119.31(9) . . ?
C11 C16 H16 119.7(6) . . ?
C15 C16 H16 120.9(6) . . ?
C14 C17 H17A 110.2(10) . . ?
C14 C17 H17B 115.2(8) . . ?
H17A C17 H17B 106.1(13) . . ?
C14 C17 H17C 110.8(8) . . ?
H17A C17 H17C 108.0(12) . . ?
H17B C17 H17C 106.2(12) . . ?

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
O2 S1 C1 C2 -159.23(8) . . . . ?
O1 S1 C1 C2 -29.29(9) . . . . ?
C5 S1 C1 C2 85.92(8) . . . . ?
O2 S1 C1 C3 25.36(8) . . . . ?
O1 S1 C1 C3 155.30(7) . . . . ?
C5 S1 C1 C3 -89.48(8) . . . . ?
C11 N2 C2 C1 -162.13(8) . . . . ?
C11 N2 C2 S2 17.15(12) . . . . ?
C3 C1 C2 N2 -167.02(9) . . . . ?
S1 C1 C2 N2 17.92(13) . . . . ?
C3 C1 C2 S2 13.65(12) . . . . ?
S1 C1 C2 S2 -161.41(5) . . . . ?
C4 S2 C2 N2 35.94(8) . . . . ?
C4 S2 C2 C1 -144.73(7) . . . . ?
C2 C1 C3 N1 154.0(18) . . . . ?
S1 C1 C3 N1 -30.4(19) . . . . ?
O2 S1 C5 C10 -5.04(9) . . . . ?
O1 S1 C5 C10 -134.53(7) . . . . ?
C1 S1 C5 C10 110.04(7) . . . . ?
O2 S1 C5 C6 176.66(7) . . . . ?
O1 S1 C5 C6 47.18(8) . . . . ?
C1 S1 C5 C6 -68.26(8) . . . . ?
C10 C5 C6 C7 -0.18(14) . . . . ?
S1 C5 C6 C7 178.08(8) . . . . ?
C5 C6 C7 C8 0.97(15) . . . . ?
C6 C7 C8 C9 -0.75(16) . . . . ?
C7 C8 C9 C10 -0.27(16) . . . . ?
C6 C5 C10 C9 -0.82(13) . . . . ?
S1 C5 C10 C9 -179.09(7) . . . . ?
C8 C9 C10 C5 1.04(14) . . . . ?
C2 N2 C11 C16 57.87(13) . . . . ?
C2 N2 C11 C12 -122.54(10) . . . . ?
C16 C11 C12 C13 -1.21(13) . . . . ?
N2 C11 C12 C13 179.21(8) . . . . ?
C11 C12 C13 C14 -0.48(14) . . . . ?
C12 C13 C14 C15 1.15(14) . . . . ?
C12 C13 C14 C17 -178.79(9) . . . . ?
C13 C14 C15 C16 -0.17(14) . . . . ?
C17 C14 C15 C16 179.77(10) . . . . ?
C12 C11 C16 C15 2.16(13) . . . . ?
N2 C11 C16 C15 -178.25(8) . . . . ?
C14 C15 C16 C11 -1.47(14) . . . . ?

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
N2 H2 O1 0.847(14) 2.095(14) 2.7780(11) 137.3(11) .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        40.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_TS796
_database_code_depnum_ccdc_archive 'CCDC 897058'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O2 S2'
_chemical_formula_sum            'C17 H16 N2 O2 S2'
_chemical_formula_weight         344.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.3586(16)
_cell_length_b                   5.6119(2)
_cell_length_c                   24.1160(15)
_cell_angle_alpha                90.0
_cell_angle_beta                 122.985(8)
_cell_angle_gamma                90.0
_cell_volume                     3332.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12462
_cell_measurement_theta_min      3.9410
_cell_measurement_theta_max      45.6737

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80327
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            54264
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_sigmaI/netI    0.0998
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         45.75
_reflns_number_total             14231
_reflns_number_gt                7127
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0270P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         14231
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.421345(8) 0.15523(4) 0.434556(10) 0.01258(4) Uani 1 1 d . . .
S2 S 0.468625(9) 0.23283(4) 0.290617(11) 0.02005(5) Uani 1 1 d . . .
O1 O 0.44059(2) 0.39031(11) 0.46180(3) 0.01708(12) Uani 1 1 d . . .
O2 O 0.43913(2) -0.04440(11) 0.47896(3) 0.01869(12) Uani 1 1 d . . .
N1 N 0.39151(3) -0.26644(14) 0.30504(4) 0.01999(14) Uani 1 1 d . . .
N2 N 0.50148(3) 0.42567(13) 0.40531(4) 0.01399(12) Uani 1 1 d . . .
H2 H 0.5047(4) 0.4345(19) 0.4384(6) 0.013(3) Uiso 1 1 d . . .
C1 C 0.43578(3) 0.11152(14) 0.37396(4) 0.01299(14) Uani 1 1 d . . .
C2 C 0.46759(3) 0.26332(15) 0.36272(4) 0.01268(13) Uani 1 1 d . . .
C3 C 0.41174(3) -0.09588(15) 0.33565(4) 0.01475(14) Uani 1 1 d . . .
C4 C 0.39730(4) 0.2271(2) 0.22506(5) 0.0256(2) Uani 1 1 d . . .
H4A H 0.3972(6) 0.278(2) 0.1881(7) 0.041(4) Uiso 1 1 d . . .
H4B H 0.3797(6) 0.329(3) 0.2356(8) 0.049(4) Uiso 1 1 d . . .
H4C H 0.3838(5) 0.072(2) 0.2192(6) 0.032(3) Uiso 1 1 d . . .
C5 C 0.34939(3) 0.15608(15) 0.38956(4) 0.01417(13) Uani 1 1 d . . .
C6 C 0.32073(4) 0.34747(17) 0.34829(5) 0.02048(17) Uani 1 1 d . . .
H6 H 0.3384(5) 0.474(2) 0.3414(6) 0.024(3) Uiso 1 1 d . . .
C7 C 0.26444(4) 0.3469(2) 0.31452(5) 0.02505(19) Uani 1 1 d . . .
H7 H 0.2449(5) 0.474(2) 0.2871(6) 0.033(3) Uiso 1 1 d . . .
C8 C 0.23756(4) 0.1592(2) 0.32237(5) 0.02483(19) Uani 1 1 d . . .
H8 H 0.2002(5) 0.160(2) 0.3003(6) 0.032(3) Uiso 1 1 d . . .
C9 C 0.26652(4) -0.03082(19) 0.36286(5) 0.02451(19) Uani 1 1 d . . .
H9 H 0.2489(5) -0.157(2) 0.3684(6) 0.030(3) Uiso 1 1 d . . .
C10 C 0.32300(3) -0.03468(17) 0.39671(4) 0.01870(16) Uani 1 1 d . . .
H10 H 0.3416(5) -0.158(2) 0.4231(6) 0.027(3) Uiso 1 1 d . . .
C11 C 0.52547(3) 0.62347(15) 0.39062(4) 0.01437(14) Uani 1 1 d . . .
H11A H 0.5262(4) 0.7570(17) 0.4147(5) 0.010(2) Uiso 1 1 d . . .
H11B H 0.5034(4) 0.6566(19) 0.3444(6) 0.016(3) Uiso 1 1 d . . .
C12 C 0.58318(3) 0.58160(15) 0.40963(4) 0.01427(14) Uani 1 1 d . . .
C13 C 0.61337(4) 0.38436(18) 0.44554(5) 0.02194(18) Uani 1 1 d . . .
H13 H 0.5979(5) 0.270(2) 0.4574(6) 0.029(3) Uiso 1 1 d . . .
C14 C 0.66713(4) 0.3614(2) 0.46379(5) 0.0275(2) Uani 1 1 d . . .
H14 H 0.6879(6) 0.222(2) 0.4875(7) 0.042(4) Uiso 1 1 d . . .
C15 C 0.69094(4) 0.5332(2) 0.44663(5) 0.0260(2) Uani 1 1 d . . .
H15 H 0.7276(5) 0.519(2) 0.4581(6) 0.035(3) Uiso 1 1 d . . .
C16 C 0.66084(4) 0.7270(2) 0.40999(6) 0.0309(2) Uani 1 1 d . . .
H16 H 0.6758(6) 0.841(3) 0.3957(8) 0.050(4) Uiso 1 1 d . . .
C17 C 0.60737(4) 0.75153(18) 0.39174(6) 0.0264(2) Uani 1 1 d . . .
H17 H 0.5884(6) 0.881(3) 0.3674(8) 0.055(4) Uiso 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 O2 1.4372(7) . ?
S1 O1 1.4447(6) . ?
S1 C1 1.7462(8) . ?
S1 C5 1.7733(8) . ?
S2 C2 1.7638(8) . ?
S2 C4 1.8113(11) . ?
N1 C3 1.1561(11) . ?
N2 C2 1.3275(11) . ?
N2 C11 1.4579(11) . ?
N2 H2 0.754(11) . ?
C1 C2 1.3954(11) . ?
C1 C3 1.4130(11) . ?
C4 H4A 0.933(15) . ?
C4 H4B 0.896(16) . ?
C4 H4C 0.936(13) . ?
C5 C10 1.3861(12) . ?
C5 C6 1.3929(13) . ?
C6 C7 1.3889(13) . ?
C6 H6 0.945(12) . ?
C7 C8 1.3894(15) . ?
C7 H7 0.930(13) . ?
C8 C9 1.3819(15) . ?
C8 H8 0.921(13) . ?
C9 C10 1.3938(12) . ?
C9 H9 0.930(13) . ?
C10 H10 0.898(12) . ?
C11 C12 1.5133(11) . ?
C11 H11A 0.942(10) . ?
C11 H11B 0.955(11) . ?
C12 C13 1.3875(12) . ?
C12 C17 1.3904(13) . ?
C13 C14 1.3946(13) . ?
C13 H13 0.916(13) . ?
C14 C15 1.3802(15) . ?
C14 H14 0.966(14) . ?
C15 C16 1.3764(15) . ?
C15 H15 0.956(13) . ?
C16 C17 1.3873(13) . ?
C16 H16 0.939(16) . ?
C17 H17 0.910(16) . ?

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
O2 S1 O1 118.65(4) . . ?
O2 S1 C1 111.02(4) . . ?
O1 S1 C1 107.21(4) . . ?
O2 S1 C5 106.65(4) . . ?
O1 S1 C5 108.45(4) . . ?
C1 S1 C5 103.85(4) . . ?
C2 S2 C4 103.30(5) . . ?
C2 N2 C11 126.32(7) . . ?
C2 N2 H2 118.3(8) . . ?
C11 N2 H2 114.2(8) . . ?
C2 C1 C3 121.65(7) . . ?
C2 C1 S1 124.74(6) . . ?
C3 C1 S1 113.61(6) . . ?
N2 C2 C1 124.58(7) . . ?
N2 C2 S2 114.93(6) . . ?
C1 C2 S2 120.32(6) . . ?
N1 C3 C1 178.49(9) . . ?
S2 C4 H4A 103.2(9) . . ?
S2 C4 H4B 108.2(10) . . ?
H4A C4 H4B 111.8(13) . . ?
S2 C4 H4C 109.9(8) . . ?
H4A C4 H4C 111.1(12) . . ?
H4B C4 H4C 112.2(13) . . ?
C10 C5 C6 121.56(8) . . ?
C10 C5 S1 118.83(7) . . ?
C6 C5 S1 119.61(6) . . ?
C7 C6 C5 118.69(9) . . ?
C7 C6 H6 119.3(7) . . ?
C5 C6 H6 122.0(7) . . ?
C6 C7 C8 120.32(9) . . ?
C6 C7 H7 119.4(8) . . ?
C8 C7 H7 120.3(8) . . ?
C9 C8 C7 120.30(8) . . ?
C9 C8 H8 119.6(8) . . ?
C7 C8 H8 120.1(8) . . ?
C8 C9 C10 120.26(9) . . ?
C8 C9 H9 121.0(8) . . ?
C10 C9 H9 118.7(8) . . ?
C5 C10 C9 118.85(9) . . ?
C5 C10 H10 121.2(8) . . ?
C9 C10 H10 119.9(8) . . ?
N2 C11 C12 114.67(7) . . ?
N2 C11 H11A 107.8(6) . . ?
C12 C11 H11A 107.0(6) . . ?
N2 C11 H11B 108.7(7) . . ?
C12 C11 H11B 108.7(7) . . ?
H11A C11 H11B 109.8(9) . . ?
C13 C12 C17 118.70(8) . . ?
C13 C12 C11 122.84(7) . . ?
C17 C12 C11 118.44(8) . . ?
C12 C13 C14 119.95(9) . . ?
C12 C13 H13 119.7(8) . . ?
C14 C13 H13 120.4(8) . . ?
C15 C14 C13 120.79(9) . . ?
C15 C14 H14 119.1(9) . . ?
C13 C14 H14 120.1(9) . . ?
C16 C15 C14 119.43(9) . . ?
C16 C15 H15 118.5(8) . . ?
C14 C15 H15 122.0(8) . . ?
C15 C16 C17 120.15(10) . . ?
C15 C16 H16 120.4(9) . . ?
C17 C16 H16 119.4(9) . . ?
C16 C17 C12 120.96(9) . . ?
C16 C17 H17 118.2(10) . . ?
C12 C17 H17 120.8(10) . . ?

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
O2 S1 C1 C2 -121.97(7) . . . . ?
O1 S1 C1 C2 9.08(8) . . . . ?
C5 S1 C1 C2 123.77(7) . . . . ?
O2 S1 C1 C3 58.34(7) . . . . ?
O1 S1 C1 C3 -170.61(6) . . . . ?
C5 S1 C1 C3 -55.93(7) . . . . ?
C11 N2 C2 C1 -164.37(8) . . . . ?
C11 N2 C2 S2 20.33(10) . . . . ?
C3 C1 C2 N2 -163.11(8) . . . . ?
S1 C1 C2 N2 17.22(12) . . . . ?
C3 C1 C2 S2 11.95(11) . . . . ?
S1 C1 C2 S2 -167.72(4) . . . . ?
C4 S2 C2 N2 -134.08(7) . . . . ?
C4 S2 C2 C1 50.40(8) . . . . ?
C2 C1 C3 N1 -176(100) . . . . ?
S1 C1 C3 N1 4(4) . . . . ?
O2 S1 C5 C10 -7.64(8) . . . . ?
O1 S1 C5 C10 -136.50(7) . . . . ?
C1 S1 C5 C10 109.71(7) . . . . ?
O2 S1 C5 C6 172.08(7) . . . . ?
O1 S1 C5 C6 43.22(8) . . . . ?
C1 S1 C5 C6 -70.58(8) . . . . ?
C10 C5 C6 C7 0.98(14) . . . . ?
S1 C5 C6 C7 -178.73(8) . . . . ?
C5 C6 C7 C8 0.45(15) . . . . ?
C6 C7 C8 C9 -1.27(16) . . . . ?
C7 C8 C9 C10 0.66(15) . . . . ?
C6 C5 C10 C9 -1.57(14) . . . . ?
S1 C5 C10 C9 178.14(7) . . . . ?
C8 C9 C10 C5 0.73(15) . . . . ?
C2 N2 C11 C12 -99.79(9) . . . . ?
N2 C11 C12 C13 -7.69(12) . . . . ?
N2 C11 C12 C17 174.02(9) . . . . ?
C17 C12 C13 C14 0.92(14) . . . . ?
C11 C12 C13 C14 -177.36(9) . . . . ?
C12 C13 C14 C15 0.09(16) . . . . ?
C13 C14 C15 C16 -1.25(17) . . . . ?
C14 C15 C16 C17 1.38(18) . . . . ?
C15 C16 C17 C12 -0.35(18) . . . . ?
C13 C12 C17 C16 -0.80(16) . . . . ?
C11 C12 C17 C16 177.56(10) . . . . ?

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
N2 H2 O1 0.754(11) 2.253(11) 2.7826(9) 128.2(10) .
N2 H2 O1 0.754(11) 2.264(11) 2.8801(10) 139.6(10) 5_666

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        45.75
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_TS797
_database_code_depnum_ccdc_archive 'CCDC 897059'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 F N2 O2 S2'
_chemical_formula_sum            'C16 H13 F N2 O2 S2'
_chemical_formula_weight         348.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_int_tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3288(2)
_cell_length_b                   11.2945(2)
_cell_length_c                   17.1609(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 100.643(2)
_cell_angle_gamma                90.0
_cell_volume                     1586.55(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12130
_cell_measurement_theta_min      2.9541
_cell_measurement_theta_max      45.3523

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur-S, Sapphire3 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            56056
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         45.47
_reflns_number_total             13383
_reflns_number_gt                8950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.5300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13383
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.52222(3) 0.55504(2) 0.340961(15) 0.01703(5) Uani 1 1 d . . .
S2 S 0.10714(3) 0.42928(2) 0.431585(16) 0.01902(5) Uani 1 1 d . . .
O1 O 0.62683(10) 0.45222(7) 0.34680(5) 0.02346(15) Uani 1 1 d . . .
O2 O 0.59256(10) 0.67043(7) 0.35928(5) 0.02332(15) Uani 1 1 d . . .
N1 N 0.28808(17) 0.72506(9) 0.46170(7) 0.0324(2) Uani 1 1 d . . .
N2 N 0.37439(11) 0.32214(7) 0.39473(6) 0.01878(15) Uani 1 1 d . . .
H2 H 0.473(2) 0.3277(16) 0.3932(10) 0.026(4) Uiso 1 1 d . . .
C1 C 0.37687(13) 0.53337(8) 0.40140(6) 0.01767(15) Uani 1 1 d . . .
C2 C 0.30163(12) 0.42417(8) 0.40761(6) 0.01628(14) Uani 1 1 d . . .
C3 C 0.32379(15) 0.63776(9) 0.43414(6) 0.02170(18) Uani 1 1 d . . .
C4 C 0.09860(14) 0.30075(9) 0.49323(7) 0.02141(18) Uani 1 1 d . . .
H4A H 0.001(2) 0.3138(16) 0.5141(11) 0.029(4) Uiso 1 1 d . . .
H4B H 0.083(2) 0.2307(17) 0.4635(11) 0.030(4) Uiso 1 1 d . . .
H4C H 0.192(3) 0.2983(19) 0.5315(12) 0.042(5) Uiso 1 1 d . . .
C5 C 0.40503(12) 0.56008(8) 0.24426(6) 0.01578(14) Uani 1 1 d . . .
C6 C 0.37272(14) 0.45604(9) 0.20075(6) 0.02007(17) Uani 1 1 d . . .
H6 H 0.415(2) 0.3820(16) 0.2220(10) 0.025(4) Uiso 1 1 d . . .
C7 C 0.27589(15) 0.46176(10) 0.12537(7) 0.02339(19) Uani 1 1 d . . .
H7 H 0.255(2) 0.3894(19) 0.0948(12) 0.040(5) Uiso 1 1 d . . .
C8 C 0.21438(14) 0.56962(10) 0.09458(7) 0.02264(18) Uani 1 1 d . . .
H8 H 0.152(2) 0.5731(16) 0.0422(12) 0.032(5) Uiso 1 1 d . . .
C9 C 0.24664(13) 0.67291(9) 0.13896(6) 0.01992(16) Uani 1 1 d . . .
H9 H 0.205(2) 0.7477(16) 0.1176(10) 0.028(4) Uiso 1 1 d . . .
C10 C 0.34158(12) 0.66859(8) 0.21457(6) 0.01693(15) Uani 1 1 d . . .
H10 H 0.360(2) 0.7387(15) 0.2480(10) 0.023(4) Uiso 1 1 d . . .
C11 C 0.29715(12) 0.21249(8) 0.36900(6) 0.01670(15) Uani 1 1 d . . .
C12 C 0.35453(13) 0.10955(9) 0.40906(7) 0.01978(17) Uani 1 1 d . . .
H12 H 0.442(2) 0.1130(16) 0.4552(10) 0.026(4) Uiso 1 1 d . . .
C13 C 0.28678(15) 0.00099(9) 0.38295(8) 0.0256(2) Uani 1 1 d . . .
H13 H 0.333(2) -0.0731(17) 0.4092(12) 0.033(5) Uiso 1 1 d . . .
C14 C 0.16266(15) -0.00040(10) 0.31737(8) 0.0275(2) Uani 1 1 d . . .
C15 C 0.10375(15) 0.10041(12) 0.27672(8) 0.0275(2) Uani 1 1 d . . .
H15 H 0.014(2) 0.0958(18) 0.2325(12) 0.036(5) Uiso 1 1 d . . .
C16 C 0.17269(14) 0.20865(10) 0.30274(7) 0.02233(18) Uani 1 1 d . . .
H16 H 0.143(2) 0.2801(17) 0.2761(11) 0.030(4) Uiso 1 1 d . . .
F1 F 0.09735(13) -0.10632(8) 0.29148(7) 0.0447(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
S1 O2 1.4396(8) . ?
S1 O1 1.4442(8) . ?
S1 C1 1.7507(11) . ?
S1 C5 1.7639(10) . ?
S2 C2 1.7444(10) . ?
S2 C4 1.8055(11) . ?
N1 C3 1.1560(15) . ?
N2 C2 1.3393(13) . ?
N2 C11 1.4275(12) . ?
N2 H2 0.830(18) . ?
C1 C2 1.3964(13) . ?
C1 C3 1.4118(15) . ?
C4 H4A 0.960(19) . ?
C4 H4B 0.937(19) . ?
C4 H4C 0.92(2) . ?
C5 C6 1.3916(14) . ?
C5 C10 1.3934(13) . ?
C6 C7 1.3937(16) . ?
C6 H6 0.954(18) . ?
C7 C8 1.3878(16) . ?
C7 H7 0.97(2) . ?
C8 C9 1.3920(15) . ?
C8 H8 0.95(2) . ?
C9 C10 1.3900(14) . ?
C9 H9 0.961(18) . ?
C10 H10 0.974(17) . ?
C11 C12 1.3898(14) . ?
C11 C16 1.3906(15) . ?
C12 C13 1.3889(15) . ?
C12 H12 0.972(18) . ?
C13 C14 1.3804(19) . ?
C13 H13 0.994(19) . ?
C14 F1 1.3546(13) . ?
C14 C15 1.378(2) . ?
C15 C16 1.3888(16) . ?
C15 H15 0.96(2) . ?
C16 H16 0.938(19) . ?

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
O2 S1 O1 119.79(5) . . ?
O2 S1 C1 107.17(5) . . ?
O1 S1 C1 108.71(5) . . ?
O2 S1 C5 107.97(5) . . ?
O1 S1 C5 108.25(5) . . ?
C1 S1 C5 103.82(5) . . ?
C2 S2 C4 104.50(5) . . ?
C2 N2 C11 127.29(9) . . ?
C2 N2 H2 114.9(12) . . ?
C11 N2 H2 116.6(12) . . ?
C2 C1 C3 121.96(10) . . ?
C2 C1 S1 122.54(8) . . ?
C3 C1 S1 114.88(7) . . ?
N2 C2 C1 121.62(9) . . ?
N2 C2 S2 122.38(7) . . ?
C1 C2 S2 115.99(7) . . ?
N1 C3 C1 176.69(13) . . ?
S2 C4 H4A 102.9(11) . . ?
S2 C4 H4B 112.1(11) . . ?
H4A C4 H4B 106.9(15) . . ?
S2 C4 H4C 108.9(13) . . ?
H4A C4 H4C 113.5(17) . . ?
H4B C4 H4C 112.2(17) . . ?
C6 C5 C10 121.58(9) . . ?
C6 C5 S1 119.75(7) . . ?
C10 C5 S1 118.62(7) . . ?
C5 C6 C7 118.71(9) . . ?
C5 C6 H6 120.9(10) . . ?
C7 C6 H6 120.4(10) . . ?
C8 C7 C6 120.25(10) . . ?
C8 C7 H7 121.2(12) . . ?
C6 C7 H7 118.6(12) . . ?
C7 C8 C9 120.47(10) . . ?
C7 C8 H8 119.6(11) . . ?
C9 C8 H8 119.9(11) . . ?
C10 C9 C8 120.02(9) . . ?
C10 C9 H9 119.5(11) . . ?
C8 C9 H9 120.5(11) . . ?
C9 C10 C5 118.96(9) . . ?
C9 C10 H10 121.6(10) . . ?
C5 C10 H10 119.4(10) . . ?
C12 C11 C16 120.98(9) . . ?
C12 C11 N2 118.59(9) . . ?
C16 C11 N2 120.35(9) . . ?
C13 C12 C11 119.79(10) . . ?
C13 C12 H12 119.8(11) . . ?
C11 C12 H12 120.4(11) . . ?
C14 C13 C12 118.13(11) . . ?
C14 C13 H13 122.0(11) . . ?
C12 C13 H13 119.7(11) . . ?
F1 C14 C15 118.68(12) . . ?
F1 C14 C13 118.19(12) . . ?
C15 C14 C13 123.13(10) . . ?
C14 C15 C16 118.51(11) . . ?
C14 C15 H15 120.4(12) . . ?
C16 C15 H15 121.0(12) . . ?
C15 C16 C11 119.46(11) . . ?
C15 C16 H16 122.9(11) . . ?
C11 C16 H16 117.6(11) . . ?

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
O2 S1 C1 C2 -170.49(8) . . . . ?
O1 S1 C1 C2 -39.67(10) . . . . ?
C5 S1 C1 C2 75.41(9) . . . . ?
O2 S1 C1 C3 18.40(10) . . . . ?
O1 S1 C1 C3 149.22(8) . . . . ?
C5 S1 C1 C3 -95.70(9) . . . . ?
C11 N2 C2 C1 -153.82(10) . . . . ?
C11 N2 C2 S2 25.22(15) . . . . ?
C3 C1 C2 N2 -163.11(10) . . . . ?
S1 C1 C2 N2 26.41(14) . . . . ?
C3 C1 C2 S2 17.80(13) . . . . ?
S1 C1 C2 S2 -152.69(6) . . . . ?
C4 S2 C2 N2 36.01(10) . . . . ?
C4 S2 C2 C1 -144.90(8) . . . . ?
C2 C1 C3 N1 146(2) . . . . ?
S1 C1 C3 N1 -43(2) . . . . ?
O2 S1 C5 C6 156.80(9) . . . . ?
O1 S1 C5 C6 25.74(10) . . . . ?
C1 S1 C5 C6 -89.66(9) . . . . ?
O2 S1 C5 C10 -25.67(10) . . . . ?
O1 S1 C5 C10 -156.74(8) . . . . ?
C1 S1 C5 C10 87.86(8) . . . . ?
C10 C5 C6 C7 0.71(16) . . . . ?
S1 C5 C6 C7 178.16(9) . . . . ?
C5 C6 C7 C8 0.45(17) . . . . ?
C6 C7 C8 C9 -0.93(18) . . . . ?
C7 C8 C9 C10 0.25(17) . . . . ?
C8 C9 C10 C5 0.88(16) . . . . ?
C6 C5 C10 C9 -1.37(15) . . . . ?
S1 C5 C10 C9 -178.85(8) . . . . ?
C2 N2 C11 C12 -132.62(11) . . . . ?
C2 N2 C11 C16 50.57(16) . . . . ?
C16 C11 C12 C13 -0.16(16) . . . . ?
N2 C11 C12 C13 -176.95(10) . . . . ?
C11 C12 C13 C14 -0.27(17) . . . . ?
C12 C13 C14 F1 179.50(11) . . . . ?
C12 C13 C14 C15 0.26(19) . . . . ?
F1 C14 C15 C16 -179.05(12) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C11 -0.61(18) . . . . ?
C12 C11 C16 C15 0.61(17) . . . . ?
N2 C11 C16 C15 177.34(11) . . . . ?

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
N2 H2 O1 0.830(18) 2.152(18) 2.8097(12) 136.2(16) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        45.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_TS799
_database_code_depnum_ccdc_archive 'CCDC 897060'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N3 O4 S2'
_chemical_formula_sum            'C16 H13 N3 O4 S2'
_chemical_formula_weight         375.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_int_tables_number      14



loop_
_symmetry_equiv_pos_as_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                   11.226(2)
_cell_length_b                   10.807(2)
_cell_length_c                   14.909(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.24(3)
_cell_angle_gamma                90.00
_cell_volume                     1697.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      49.12

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur-S, Sapphire3 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_reflns_number            129050
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         49.12
_reflns_number_total             17254
_reflns_number_gt                14297
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0506P)²+0.2157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         17254
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        49.12
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.085

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.569805(14) -0.029001(13) 0.855541(10) 0.01283(3) Uani 1 1 d . . .
S2 S 0.291281(14) 0.237240(13) 0.868998(11) 0.01400(3) Uani 1 1 d . . .
O1 O 0.68220(5) -0.05950(5) 0.93507(4) 0.02017(8) Uani 1 1 d . . .
O2 O 0.48500(5) -0.12664(4) 0.80547(4) 0.01881(8) Uani 1 1 d . . .
O3 O -0.24900(5) 0.01352(5) 0.48465(4) 0.02254(9) Uani 1 1 d . . .
O4 O -0.29158(5) -0.11925(6) 0.57856(5) 0.02476(10) Uani 1 1 d . . .
N1 N 0.63142(6) 0.22320(5) 1.02372(4) 0.01802(8) Uani 1 1 d . . .
N2 N 0.27699(5) -0.00741(5) 0.82311(4) 0.01465(7) Uani 1 1 d . . .
N3 N -0.21934(5) -0.04791(5) 0.55866(4) 0.01705(8) Uani 1 1 d . . .
C1 C 0.48350(5) 0.08016(5) 0.89515(4) 0.01220(7) Uani 1 1 d . . .
C2 C 0.35109(5) 0.09106(5) 0.85961(4) 0.01189(7) Uani 1 1 d . . .
C3 C 0.56146(5) 0.16289(5) 0.96431(4) 0.01325(7) Uani 1 1 d . . .
C4 C 0.14153(6) 0.20883(6) 0.88514(5) 0.01647(8) Uani 1 1 d . . .
C5 C 0.61814(5) 0.05341(5) 0.77180(4) 0.01274(7) Uani 1 1 d . . .
C6 C 0.53136(6) 0.07001(6) 0.67949(4) 0.01651(9) Uani 1 1 d . . .
C7 C 0.56695(7) 0.14111(7) 0.61505(5) 0.02041(10) Uani 1 1 d . . .
C8 C 0.68715(7) 0.19500(7) 0.64339(5) 0.02035(10) Uani 1 1 d . . .
C9 C 0.77269(6) 0.17713(7) 0.73543(5) 0.01955(10) Uani 1 1 d . . .
C10 C 0.73892(6) 0.10577(6) 0.80072(5) 0.01662(9) Uani 1 1 d . . .
C11 C 0.15131(5) -0.01045(5) 0.75724(4) 0.01272(7) Uani 1 1 d . . .
C12 C 0.11150(6) 0.06705(5) 0.67755(4) 0.01477(8) Uani 1 1 d . . .
C13 C -0.01113(6) 0.05542(5) 0.61187(4) 0.01507(8) Uani 1 1 d . . .
C14 C -0.09016(5) -0.03432(5) 0.62757(4) 0.01384(7) Uani 1 1 d . . .
C15 C -0.05206(6) -0.11235(6) 0.70660(4) 0.01599(8) Uani 1 1 d . . .
C16 C 0.07021(6) -0.10017(5) 0.77187(4) 0.01547(8) Uani 1 1 d . . .
H2 H 0.3133(14) -0.0790(14) 0.8361(11) 0.032(3) Uiso 1 1 d . . .
H4A H 0.0768(12) 0.1982(12) 0.8258(9) 0.022(3) Uiso 1 1 d . . .
H4B H 0.1480(13) 0.1414(13) 0.9265(10) 0.027(3) Uiso 1 1 d . . .
H4C H 0.1257(13) 0.2803(14) 0.9148(10) 0.032(3) Uiso 1 1 d . . .
H6 H 0.4489(13) 0.0306(13) 0.6603(10) 0.028(3) Uiso 1 1 d . . .
H7 H 0.5071(13) 0.1538(13) 0.5507(10) 0.028(3) Uiso 1 1 d . . .
H8 H 0.7116(13) 0.2422(14) 0.5977(11) 0.031(3) Uiso 1 1 d . . .
H9 H 0.8539(13) 0.2165(14) 0.7526(10) 0.031(3) Uiso 1 1 d . . .
H10 H 0.7964(14) 0.0932(15) 0.8632(11) 0.038(4) Uiso 1 1 d . . .
H12 H 0.1698(11) 0.1264(12) 0.6671(9) 0.020(3) Uiso 1 1 d . . .
H13 H -0.0413(13) 0.1041(13) 0.5570(10) 0.027(3) Uiso 1 1 d . . .
H15 H -0.1113(12) -0.1721(13) 0.7125(9) 0.023(3) Uiso 1 1 d . . .
H16 H 0.0973(12) -0.1527(13) 0.8262(9) 0.026(3) Uiso 1 1 d . . .
O5 O 1.0137(9) -0.0509(9) 0.9764(7) 0.037(3) Uiso 0.088(4) 1 d P . .


_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 O1 1.4392(8) . ?
S1 O2 1.4441(6) . ?
S1 C1 1.7536(6) . ?
S1 C5 1.7650(6) . ?
S2 C2 1.7411(6) . ?
S2 C4 1.8051(7) . ?
O3 N3 1.2307(8) . ?
O4 N3 1.2276(8) . ?
N1 C3 1.1596(8) . ?
N2 C2 1.3443(8) . ?
N2 C11 1.4133(9) . ?
N3 C14 1.4660(9) . ?
C1 C2 1.3997(8) . ?
C1 C3 1.4156(9) . ?
C5 C10 1.3928(9) . ?
C5 C6 1.3956(10) . ?
C10 C9 1.3933(10) . ?
C9 C8 1.3895(12) . ?
C8 C7 1.3942(11) . ?
C7 C6 1.3924(9) . ?
C11 C12 1.3948(8) . ?
C11 C16 1.3979(8) . ?
C12 C13 1.3918(10) . ?
C13 C14 1.3879(8) . ?
C14 C15 1.3905(9) . ?
C15 C16 1.3871(10) . ?
O5 O5 1.395(19) 3_757 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.46(4) . . ?
O1 S1 C1 107.80(3) . . ?
O2 S1 C1 108.87(3) . . ?
O1 S1 C5 107.57(3) . . ?
O2 S1 C5 108.19(3) . . ?
C1 S1 C5 103.86(3) . . ?
C2 S2 C4 105.03(3) . . ?
C2 N2 C11 128.96(5) . . ?
O4 N3 O3 123.99(6) . . ?
O4 N3 C14 118.00(6) . . ?
O3 N3 C14 118.00(6) . . ?
C2 C1 C3 122.04(5) . . ?
C2 C1 S1 124.55(4) . . ?
C3 C1 S1 113.32(4) . . ?
N2 C2 C1 120.93(5) . . ?
N2 C2 S2 123.30(4) . . ?
C1 C2 S2 115.75(4) . . ?
N1 C3 C1 174.83(6) . . ?
C10 C5 C6 121.71(6) . . ?
C10 C5 S1 119.38(5) . . ?
C6 C5 S1 118.81(4) . . ?
C5 C10 C9 118.66(6) . . ?
C8 C9 C10 120.32(6) . . ?
C9 C8 C7 120.46(6) . . ?
C6 C7 C8 120.01(6) . . ?
C7 C6 C5 118.84(6) . . ?
C12 C11 C16 121.02(6) . . ?
C12 C11 N2 121.77(5) . . ?
C16 C11 N2 117.08(5) . . ?
C13 C12 C11 119.50(6) . . ?
C14 C13 C12 118.61(5) . . ?
C13 C14 C15 122.66(6) . . ?
C13 C14 N3 119.13(5) . . ?
C15 C14 N3 118.21(6) . . ?
C16 C15 C14 118.45(6) . . ?
C15 C16 C11 119.75(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
O1 S1 C1 C2 -148.87(5) . . . . ?
O2 S1 C1 C2 -17.91(6) . . . . ?
C5 S1 C1 C2 97.18(5) . . . . ?
O1 S1 C1 C3 34.43(5) . . . . ?
O2 S1 C1 C3 165.39(4) . . . . ?
C5 S1 C1 C3 -79.52(5) . . . . ?
C11 N2 C2 C1 -156.58(6) . . . . ?
C11 N2 C2 S2 25.15(9) . . . . ?
C3 C1 C2 N2 -155.58(5) . . . . ?
S1 C1 C2 N2 28.00(8) . . . . ?
C3 C1 C2 S2 22.82(7) . . . . ?
S1 C1 C2 S2 -153.61(3) . . . . ?
C4 S2 C2 N2 30.24(5) . . . . ?
C4 S2 C2 C1 -148.11(4) . . . . ?
C2 C1 C3 N1 146.1(7) . . . . ?
S1 C1 C3 N1 -37.1(7) . . . . ?
O1 S1 C5 C10 -17.52(6) . . . . ?
O2 S1 C5 C10 -147.83(5) . . . . ?
C1 S1 C5 C10 96.58(5) . . . . ?
O1 S1 C5 C6 165.94(5) . . . . ?
O2 S1 C5 C6 35.62(6) . . . . ?
C1 S1 C5 C6 -79.96(5) . . . . ?
C6 C5 C10 C9 0.47(9) . . . . ?
S1 C5 C10 C9 -175.97(5) . . . . ?
C5 C10 C9 C8 -0.17(10) . . . . ?
C10 C9 C8 C7 -0.45(11) . . . . ?
C9 C8 C7 C6 0.76(11) . . . . ?
C8 C7 C6 C5 -0.46(11) . . . . ?
C10 C5 C6 C7 -0.16(10) . . . . ?
S1 C5 C6 C7 176.31(5) . . . . ?
C2 N2 C11 C12 42.08(9) . . . . ?
C2 N2 C11 C16 -141.92(6) . . . . ?
C16 C11 C12 C13 0.41(9) . . . . ?
N2 C11 C12 C13 176.26(5) . . . . ?
C11 C12 C13 C14 -0.49(9) . . . . ?
C12 C13 C14 C15 0.51(9) . . . . ?
C12 C13 C14 N3 -179.70(5) . . . . ?
O4 N3 C14 C13 -173.00(6) . . . . ?
O3 N3 C14 C13 6.53(9) . . . . ?
O4 N3 C14 C15 6.81(9) . . . . ?
O3 N3 C14 C15 -173.66(6) . . . . ?
C13 C14 C15 C16 -0.41(9) . . . . ?
N3 C14 C15 C16 179.79(6) . . . . ?
C14 C15 C16 C11 0.31(9) . . . . ?
C12 C11 C16 C15 -0.32(9) . . . . ?
N2 C11 C16 C15 -176.36(6) . . . . ?



####################################################################### 
# 
# 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_TS812
_database_code_depnum_ccdc_archive 'CCDC 897061'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O3 S2'
_chemical_formula_sum            'C17 H16 N2 O3 S2'
_chemical_formula_weight         360.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_int_tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6156(2)
_cell_length_b                   20.5840(4)
_cell_length_c                   9.6518(2)
_cell_angle_alpha                90.0
_cell_angle_beta                 101.108(2)
_cell_angle_gamma                90.0
_cell_volume                     1679.62(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11293
_cell_measurement_theta_min      3.6532
_cell_measurement_theta_max      37.5791

_exptl_crystal_description       needle
_exptl_crystal_colour            yellowish
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33211
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         37.69
_reflns_number_total             8593
_reflns_number_gt                5829
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8593
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.53414(2) 0.579932(10) 0.80107(2) 0.01702(5) Uani 1 1 d . . .
S2 S 0.10413(3) 0.485420(12) 0.85189(2) 0.02145(5) Uani 1 1 d . . .
O1 O 0.62629(7) 0.52639(3) 0.76390(7) 0.02181(13) Uani 1 1 d . . .
O2 O 0.61061(8) 0.62986(3) 0.89416(7) 0.02379(14) Uani 1 1 d . . .
O3 O 0.10544(9) 0.27678(3) 0.32348(8) 0.02832(15) Uani 1 1 d . . .
N1 N 0.29130(10) 0.62432(4) 1.05578(9) 0.02552(17) Uani 1 1 d . . .
N2 N 0.36389(9) 0.44567(4) 0.75669(8) 0.01818(14) Uani 1 1 d . . .
H2 H 0.4660(15) 0.4490(6) 0.7638(12) 0.027(3) Uiso 1 1 d . . .
C1 C 0.37901(10) 0.54841(4) 0.87443(9) 0.01773(15) Uani 1 1 d . . .
C2 C 0.29732(10) 0.49191(4) 0.82366(9) 0.01716(15) Uani 1 1 d . . .
C3 C 0.32695(11) 0.58974(4) 0.97353(9) 0.01939(16) Uani 1 1 d . . .
C4 C 0.07105(12) 0.39889(5) 0.86131(11) 0.02473(19) Uani 1 1 d . . .
H4A H -0.0204(16) 0.3954(6) 0.9024(13) 0.035(3) Uiso 1 1 d . . .
H4B H 0.0429(14) 0.3775(6) 0.7666(13) 0.030(3) Uiso 1 1 d . . .
H4C H 0.1638(16) 0.3777(6) 0.9204(14) 0.037(3) Uiso 1 1 d . . .
C5 C 0.43685(10) 0.61724(4) 0.64345(9) 0.01640(15) Uani 1 1 d . . .
C6 C 0.38380(10) 0.57871(4) 0.52521(9) 0.01797(15) Uani 1 1 d . . .
H6 H 0.4028(12) 0.5340(6) 0.5297(11) 0.020(3) Uiso 1 1 d . . .
C7 C 0.30002(11) 0.60728(5) 0.40354(10) 0.02066(16) Uani 1 1 d . . .
H7 H 0.2684(14) 0.5825(5) 0.3238(12) 0.025(3) Uiso 1 1 d . . .
C8 C 0.27058(12) 0.67358(5) 0.40027(10) 0.02397(18) Uani 1 1 d . . .
H8 H 0.2143(14) 0.6924(6) 0.3126(12) 0.029(3) Uiso 1 1 d . . .
C9 C 0.32285(12) 0.71167(5) 0.51879(11) 0.02569(19) Uani 1 1 d . . .
H9 H 0.3032(15) 0.7580(6) 0.5170(13) 0.034(3) Uiso 1 1 d . . .
C10 C 0.40629(11) 0.68365(4) 0.64201(10) 0.02145(17) Uani 1 1 d . . .
H10 H 0.4425(14) 0.7103(6) 0.7226(12) 0.026(3) Uiso 1 1 d . . .
C11 C 0.28673(10) 0.40286(4) 0.64845(9) 0.01735(15) Uani 1 1 d . . .
C12 C 0.33284(11) 0.33792(4) 0.65180(10) 0.02062(17) Uani 1 1 d . . .
H12 H 0.4081(15) 0.3241(6) 0.7310(12) 0.030(3) Uiso 1 1 d . . .
C13 C 0.26957(11) 0.29690(5) 0.54214(10) 0.02276(18) Uani 1 1 d . . .
H13 H 0.2991(13) 0.2512(6) 0.5437(12) 0.022(3) Uiso 1 1 d . . .
C14 C 0.15842(11) 0.32056(4) 0.42885(10) 0.02093(17) Uani 1 1 d . . .
C15 C 0.10925(11) 0.38487(5) 0.42672(10) 0.02137(17) Uani 1 1 d . . .
H15 H 0.0358(14) 0.4000(6) 0.3503(13) 0.030(3) Uiso 1 1 d . . .
C16 C 0.17501(11) 0.42620(4) 0.53692(9) 0.02000(16) Uani 1 1 d . . .
H16 H 0.1469(13) 0.4717(6) 0.5348(12) 0.023(3) Uiso 1 1 d . . .
C17 C 0.01210(14) 0.30253(6) 0.19713(11) 0.0304(2) Uani 1 1 d . . .
H17A H -0.0039(15) 0.2672(6) 0.1305(13) 0.036(3) Uiso 1 1 d . . .
H17B H -0.0928(15) 0.3171(6) 0.2098(12) 0.027(3) Uiso 1 1 d . . .
H17C H 0.0697(16) 0.3396(7) 0.1664(13) 0.040(4) Uiso 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 O2 1.4386(7) . ?
S1 O1 1.4434(7) . ?
S1 C1 1.7531(9) . ?
S1 C5 1.7651(9) . ?
S2 C2 1.7428(9) . ?
S2 C4 1.8088(11) . ?
O3 C14 1.3697(11) . ?
O3 C17 1.4271(13) . ?
N1 C3 1.1512(12) . ?
N2 C2 1.3399(11) . ?
N2 C11 1.4290(11) . ?
N2 H2 0.872(12) . ?
C1 C2 1.3984(12) . ?
C1 C3 1.4160(12) . ?
C4 H4A 0.951(13) . ?
C4 H4B 1.001(12) . ?
C4 H4C 0.989(14) . ?
C5 C10 1.3915(12) . ?
C5 C6 1.3926(12) . ?
C6 C7 1.3854(13) . ?
C6 H6 0.933(11) . ?
C7 C8 1.3873(14) . ?
C7 H7 0.920(11) . ?
C8 C9 1.3884(14) . ?
C8 H8 0.971(12) . ?
C9 C10 1.3909(13) . ?
C9 H9 0.969(13) . ?
C10 H10 0.954(12) . ?
C11 C16 1.3845(12) . ?
C11 C12 1.3931(12) . ?
C12 C13 1.3814(13) . ?
C12 H12 0.946(12) . ?
C13 C14 1.3951(13) . ?
C13 H13 0.974(11) . ?
C14 C15 1.3887(13) . ?
C15 C16 1.3942(13) . ?
C15 H15 0.929(12) . ?
C16 H16 0.967(11) . ?
C17 H17A 0.963(13) . ?
C17 H17B 0.982(12) . ?
C17 H17C 0.986(14) . ?

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
O2 S1 O1 119.55(4) . . ?
O2 S1 C1 107.77(4) . . ?
O1 S1 C1 108.45(4) . . ?
O2 S1 C5 108.16(4) . . ?
O1 S1 C5 108.10(4) . . ?
C1 S1 C5 103.69(4) . . ?
C2 S2 C4 104.35(5) . . ?
C14 O3 C17 116.26(8) . . ?
C2 N2 C11 127.49(8) . . ?
C2 N2 H2 115.2(8) . . ?
C11 N2 H2 115.2(8) . . ?
C2 C1 C3 122.20(8) . . ?
C2 C1 S1 122.53(7) . . ?
C3 C1 S1 114.58(6) . . ?
N2 C2 C1 121.77(8) . . ?
N2 C2 S2 122.10(7) . . ?
C1 C2 S2 116.13(7) . . ?
N1 C3 C1 177.00(10) . . ?
S2 C4 H4A 104.3(8) . . ?
S2 C4 H4B 113.5(7) . . ?
H4A C4 H4B 105.9(10) . . ?
S2 C4 H4C 110.2(8) . . ?
H4A C4 H4C 111.7(11) . . ?
H4B C4 H4C 111.0(11) . . ?
C10 C5 C6 121.31(8) . . ?
C10 C5 S1 119.57(7) . . ?
C6 C5 S1 119.00(7) . . ?
C7 C6 C5 119.21(8) . . ?
C7 C6 H6 121.0(7) . . ?
C5 C6 H6 119.8(7) . . ?
C6 C7 C8 120.00(9) . . ?
C6 C7 H7 119.7(7) . . ?
C8 C7 H7 120.3(7) . . ?
C7 C8 C9 120.53(9) . . ?
C7 C8 H8 118.1(7) . . ?
C9 C8 H8 121.4(7) . . ?
C8 C9 C10 120.16(9) . . ?
C8 C9 H9 120.9(7) . . ?
C10 C9 H9 118.9(7) . . ?
C9 C10 C5 118.79(9) . . ?
C9 C10 H10 119.6(7) . . ?
C5 C10 H10 121.7(7) . . ?
C16 C11 C12 120.22(8) . . ?
C16 C11 N2 120.68(8) . . ?
C12 C11 N2 118.97(8) . . ?
C13 C12 C11 120.01(8) . . ?
C13 C12 H12 122.9(7) . . ?
C11 C12 H12 117.1(7) . . ?
C12 C13 C14 119.80(9) . . ?
C12 C13 H13 121.0(7) . . ?
C14 C13 H13 119.1(7) . . ?
O3 C14 C15 123.99(8) . . ?
O3 C14 C13 115.62(8) . . ?
C15 C14 C13 120.38(8) . . ?
C14 C15 C16 119.49(9) . . ?
C14 C15 H15 119.4(7) . . ?
C16 C15 H15 121.0(7) . . ?
C11 C16 C15 120.06(8) . . ?
C11 C16 H16 119.1(7) . . ?
C15 C16 H16 120.8(7) . . ?
O3 C17 H17A 106.0(8) . . ?
O3 C17 H17B 112.8(7) . . ?
H17A C17 H17B 107.3(10) . . ?
O3 C17 H17C 108.1(8) . . ?
H17A C17 H17C 113.5(10) . . ?
H17B C17 H17C 109.3(11) . . ?

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
O2 S1 C1 C2 -168.95(7) . . . . ?
O1 S1 C1 C2 -38.20(8) . . . . ?
C5 S1 C1 C2 76.53(8) . . . . ?
O2 S1 C1 C3 20.45(8) . . . . ?
O1 S1 C1 C3 151.20(6) . . . . ?
C5 S1 C1 C3 -94.07(7) . . . . ?
C11 N2 C2 C1 -149.37(9) . . . . ?
C11 N2 C2 S2 30.32(12) . . . . ?
C3 C1 C2 N2 -164.35(8) . . . . ?
S1 C1 C2 N2 25.75(12) . . . . ?
C3 C1 C2 S2 15.94(11) . . . . ?
S1 C1 C2 S2 -153.96(5) . . . . ?
C4 S2 C2 N2 28.59(8) . . . . ?
C4 S2 C2 C1 -151.70(7) . . . . ?
C2 C1 C3 N1 157.2(18) . . . . ?
S1 C1 C3 N1 -32.2(19) . . . . ?
O2 S1 C5 C10 -17.90(8) . . . . ?
O1 S1 C5 C10 -148.69(7) . . . . ?
C1 S1 C5 C10 96.33(8) . . . . ?
O2 S1 C5 C6 165.93(7) . . . . ?
O1 S1 C5 C6 35.14(8) . . . . ?
C1 S1 C5 C6 -79.83(7) . . . . ?
C10 C5 C6 C7 0.50(13) . . . . ?
S1 C5 C6 C7 176.60(7) . . . . ?
C5 C6 C7 C8 0.33(13) . . . . ?
C6 C7 C8 C9 -0.77(14) . . . . ?
C7 C8 C9 C10 0.38(15) . . . . ?
C8 C9 C10 C5 0.44(15) . . . . ?
C6 C5 C10 C9 -0.89(14) . . . . ?
S1 C5 C10 C9 -176.96(7) . . . . ?
C2 N2 C11 C16 45.31(13) . . . . ?
C2 N2 C11 C12 -138.79(9) . . . . ?
C16 C11 C12 C13 1.38(14) . . . . ?
N2 C11 C12 C13 -174.54(8) . . . . ?
C11 C12 C13 C14 -0.60(14) . . . . ?
C17 O3 C14 C15 9.18(14) . . . . ?
C17 O3 C14 C13 -170.15(9) . . . . ?
C12 C13 C14 O3 178.38(8) . . . . ?
C12 C13 C14 C15 -0.97(14) . . . . ?
O3 C14 C15 C16 -177.56(9) . . . . ?
C13 C14 C15 C16 1.74(14) . . . . ?
C12 C11 C16 C15 -0.60(14) . . . . ?
N2 C11 C16 C15 175.25(8) . . . . ?
C14 C15 C16 C11 -0.95(14) . . . . ?

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
N2 H2 O1 0.872(12) 2.107(12) 2.7957(10) 135.3(10) .

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_TS828
_database_code_depnum_ccdc_archive 'CCDC 897062'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 I N2 O2 S2'
_chemical_formula_sum            'C16 H13 I N2 O2 S2'
_chemical_formula_weight         456.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.3814(8)
_cell_length_b                   6.2777(1)
_cell_length_c                   21.5020(7)
_cell_angle_alpha                90.0
_cell_angle_beta                 117.043(4)
_cell_angle_gamma                90.0
_cell_volume                     3412.15(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27840
_cell_measurement_theta_min      2.8930
_cell_measurement_theta_max      45.3707

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur-S, Sapphire3 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            107459
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         45.49
_reflns_number_total             14388
_reflns_number_gt                11464
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0360P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         14388
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.095377(10) -0.11802(4) 0.367959(13) 0.01830(4) Uani 1 1 d . . .
S2 S 0.027764(11) 0.25464(4) 0.482372(15) 0.02065(5) Uani 1 1 d . . .
O1 O 0.05545(4) -0.05010(18) 0.29972(4) 0.02753(18) Uani 1 1 d . . .
O2 O 0.10378(4) -0.34407(14) 0.38129(5) 0.02707(16) Uani 1 1 d . . .
N1 N 0.15082(4) -0.08614(17) 0.55472(5) 0.02357(16) Uani 1 1 d . . .
N2 N -0.00714(3) 0.12794(16) 0.35139(5) 0.01953(14) Uani 1 1 d . . .
H2 H -0.0045(9) 0.056(4) 0.3185(11) 0.032(5) Uiso 1 1 d . . .
C1 C 0.07941(4) -0.00274(16) 0.43011(5) 0.01714(13) Uani 1 1 d . . .
C2 C 0.03421(4) 0.11600(15) 0.41497(5) 0.01610(13) Uani 1 1 d . . .
C3 C 0.11770(4) -0.04538(16) 0.49956(5) 0.01780(14) Uani 1 1 d . . .
C4 C 0.08798(5) 0.41043(19) 0.51967(7) 0.0264(2) Uani 1 1 d . . .
H4A H 0.0804(9) 0.520(4) 0.5401(11) 0.034(5) Uiso 1 1 d . . .
H4B H 0.1170(9) 0.333(4) 0.5550(12) 0.031(5) Uiso 1 1 d . . .
H4C H 0.0950(10) 0.442(4) 0.4852(13) 0.044(6) Uiso 1 1 d . . .
C5 C 0.15608(4) -0.00172(16) 0.38354(5) 0.01775(14) Uani 1 1 d . . .
C6 C 0.15668(5) 0.2080(2) 0.36235(7) 0.0256(2) Uani 1 1 d . . .
H6 H 0.1253(12) 0.285(4) 0.3417(16) 0.048(7) Uiso 1 1 d . . .
C7 C 0.20492(7) 0.2988(3) 0.37569(8) 0.0326(3) Uani 1 1 d . . .
H7 H 0.2070(10) 0.431(4) 0.3614(12) 0.040(6) Uiso 1 1 d . . .
C8 C 0.25148(6) 0.1833(3) 0.40971(8) 0.0340(3) Uani 1 1 d . . .
H8 H 0.2802(14) 0.249(3) 0.4142(17) 0.046(8) Uiso 1 1 d . . .
C9 C 0.25028(6) -0.0249(3) 0.43013(9) 0.0351(3) Uani 1 1 d . . .
H9 H 0.2811(13) -0.103(5) 0.4509(16) 0.071(9) Uiso 1 1 d . . .
C10 C 0.20240(5) -0.1188(2) 0.41747(7) 0.0269(2) Uani 1 1 d . . .
H10 H 0.1998(13) -0.260(3) 0.4291(16) 0.042(7) Uiso 1 1 d . . .
C11 C -0.05110(4) 0.27011(15) 0.33265(5) 0.01676(13) Uani 1 1 d . . .
C12 C -0.09583(4) 0.20023(17) 0.33730(5) 0.01772(14) Uani 1 1 d . . .
H12 H -0.0960(8) 0.059(3) 0.3538(11) 0.029(5) Uiso 1 1 d . . .
C13 C -0.13933(4) 0.33476(15) 0.31766(5) 0.01740(14) Uani 1 1 d . . .
H13 H -0.1676(9) 0.288(3) 0.3237(11) 0.023(5) Uiso 1 1 d . . .
C14 C -0.13703(4) 0.53841(15) 0.29391(5) 0.01581(13) Uani 1 1 d . . .
C15 C -0.09233(4) 0.61003(16) 0.28912(6) 0.01957(15) Uani 1 1 d . . .
H15 H -0.0926(10) 0.749(3) 0.2697(13) 0.025(5) Uiso 1 1 d . . .
C16 C -0.04901(4) 0.47420(17) 0.30832(6) 0.02101(16) Uani 1 1 d . . .
H16 H -0.0172(8) 0.527(3) 0.3068(11) 0.028(5) Uiso 1 1 d . . .
I1 I -0.201443(3) 0.746655(10) 0.265658(4) 0.02073(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
S1 O2 1.4459(10) . ?
S1 O1 1.4515(9) . ?
S1 C1 1.7508(9) . ?
S1 C5 1.7573(11) . ?
S2 C2 1.7700(9) . ?
S2 C4 1.8093(12) . ?
N1 C3 1.1584(14) . ?
N2 C2 1.3391(13) . ?
N2 C11 1.4348(13) . ?
N2 H2 0.87(2) . ?
C1 C2 1.3883(13) . ?
C1 C3 1.4166(14) . ?
C4 H4A 0.90(2) . ?
C4 H4B 0.96(2) . ?
C4 H4C 0.87(3) . ?
C5 C10 1.3889(14) . ?
C5 C6 1.3956(16) . ?
C6 C7 1.387(2) . ?
C6 H6 0.93(3) . ?
C7 C8 1.389(2) . ?
C7 H7 0.90(2) . ?
C8 C9 1.384(3) . ?
C8 H8 0.88(3) . ?
C9 C10 1.390(2) . ?
C9 H9 0.92(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.3889(14) . ?
C11 C16 1.3953(15) . ?
C12 C13 1.3935(14) . ?
C12 H12 0.95(2) . ?
C13 C14 1.3891(13) . ?
C13 H13 0.92(2) . ?
C14 C15 1.3932(13) . ?
C14 I1 2.1000(9) . ?
C15 C16 1.3956(15) . ?
C15 H15 0.967(19) . ?
C16 H16 0.98(2) . ?

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
O2 S1 O1 118.12(6) . . ?
O2 S1 C1 109.33(5) . . ?
O1 S1 C1 107.22(5) . . ?
O2 S1 C5 108.11(5) . . ?
O1 S1 C5 108.53(6) . . ?
C1 S1 C5 104.73(5) . . ?
C2 S2 C4 101.55(5) . . ?
C2 N2 C11 124.63(8) . . ?
C2 N2 H2 116.2(15) . . ?
C11 N2 H2 118.7(15) . . ?
C2 C1 C3 122.19(8) . . ?
C2 C1 S1 125.11(7) . . ?
C3 C1 S1 112.69(7) . . ?
N2 C2 C1 123.85(8) . . ?
N2 C2 S2 116.07(7) . . ?
C1 C2 S2 120.04(7) . . ?
N1 C3 C1 175.90(11) . . ?
S2 C4 H4A 104.2(15) . . ?
S2 C4 H4B 111.9(14) . . ?
H4A C4 H4B 108.4(19) . . ?
S2 C4 H4C 106.3(17) . . ?
H4A C4 H4C 116(2) . . ?
H4B C4 H4C 110(2) . . ?
C10 C5 C6 121.43(11) . . ?
C10 C5 S1 119.48(9) . . ?
C6 C5 S1 119.09(8) . . ?
C7 C6 C5 118.54(12) . . ?
C7 C6 H6 121.6(17) . . ?
C5 C6 H6 119.8(18) . . ?
C6 C7 C8 120.50(14) . . ?
C6 C7 H7 121.5(16) . . ?
C8 C7 H7 118.0(16) . . ?
C9 C8 C7 120.36(13) . . ?
C9 C8 H8 124.4(18) . . ?
C7 C8 H8 115.1(18) . . ?
C8 C9 C10 120.10(13) . . ?
C8 C9 H9 120(2) . . ?
C10 C9 H9 120(2) . . ?
C5 C10 C9 119.08(12) . . ?
C5 C10 H10 118(2) . . ?
C9 C10 H10 123(2) . . ?
C12 C11 C16 120.87(9) . . ?
C12 C11 N2 119.33(9) . . ?
C16 C11 N2 119.78(9) . . ?
C11 C12 C13 119.97(9) . . ?
C11 C12 H12 118.6(13) . . ?
C13 C12 H12 121.4(13) . . ?
C14 C13 C12 119.08(9) . . ?
C14 C13 H13 122.6(13) . . ?
C12 C13 H13 118.2(13) . . ?
C13 C14 C15 121.38(9) . . ?
C13 C14 I1 119.94(7) . . ?
C15 C14 I1 118.68(7) . . ?
C14 C15 C16 119.36(9) . . ?
C14 C15 H15 119.8(15) . . ?
C16 C15 H15 120.7(15) . . ?
C11 C16 C15 119.34(9) . . ?
C11 C16 H16 121.4(12) . . ?
C15 C16 H16 119.2(13) . . ?

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
O2 S1 C1 C2 -124.27(10) . . . . ?
O1 S1 C1 C2 4.90(11) . . . . ?
C5 S1 C1 C2 120.08(9) . . . . ?
O2 S1 C1 C3 54.91(9) . . . . ?
O1 S1 C1 C3 -175.92(8) . . . . ?
C5 S1 C1 C3 -60.74(9) . . . . ?
C11 N2 C2 C1 -171.66(10) . . . . ?
C11 N2 C2 S2 10.78(14) . . . . ?
C3 C1 C2 N2 -167.51(10) . . . . ?
S1 C1 C2 N2 11.59(15) . . . . ?
C3 C1 C2 S2 9.96(14) . . . . ?
S1 C1 C2 S2 -170.94(6) . . . . ?
C4 S2 C2 N2 -128.43(9) . . . . ?
C4 S2 C2 C1 53.90(10) . . . . ?
C2 C1 C3 N1 -176(59) . . . . ?
S1 C1 C3 N1 5.0(17) . . . . ?
O2 S1 C5 C10 -12.45(11) . . . . ?
O1 S1 C5 C10 -141.69(9) . . . . ?
C1 S1 C5 C10 104.04(10) . . . . ?
O2 S1 C5 C6 168.49(9) . . . . ?
O1 S1 C5 C6 39.25(10) . . . . ?
C1 S1 C5 C6 -75.02(10) . . . . ?
C10 C5 C6 C7 0.20(18) . . . . ?
S1 C5 C6 C7 179.24(10) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C6 C5 C10 C9 -0.39(19) . . . . ?
S1 C5 C10 C9 -179.43(11) . . . . ?
C8 C9 C10 C5 0.7(2) . . . . ?
C2 N2 C11 C12 -92.87(13) . . . . ?
C2 N2 C11 C16 88.79(14) . . . . ?
C16 C11 C12 C13 -0.12(16) . . . . ?
N2 C11 C12 C13 -178.43(9) . . . . ?
C11 C12 C13 C14 -0.32(15) . . . . ?
C12 C13 C14 C15 0.26(15) . . . . ?
C12 C13 C14 I1 -178.89(7) . . . . ?
C13 C14 C15 C16 0.24(16) . . . . ?
I1 C14 C15 C16 179.41(8) . . . . ?
C12 C11 C16 C15 0.63(16) . . . . ?
N2 C11 C16 C15 178.93(10) . . . . ?
C14 C15 C16 C11 -0.68(16) . . . . ?

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
N2 H2 O1 0.87(2) 2.03(2) 2.7264(12) 136(2) .
N2 H2 O1 0.87(2) 2.38(2) 3.1040(12) 141(2) 2
N2 H2 S1 0.87(2) 2.76(2) 3.1677(9) 110.2(17) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        45.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.550
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.101
####################################################################### 
# 
# 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_TS829
_database_code_depnum_ccdc_archive 'CCDC 897063'
_audit_update_record             
;
2012-08-20 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 O2 S2'
_chemical_formula_sum            'C16 H14 N2 O2 S2'
_chemical_formula_weight         330.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_int_tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.0502(3)
_cell_length_b                   11.5540(4)
_cell_length_c                   13.7697(4)
_cell_angle_alpha                66.109(3)
_cell_angle_beta                 84.184(2)
_cell_angle_gamma                77.048(2)
_cell_volume                     1566.40(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17562
_cell_measurement_theta_min      3.6781
_cell_measurement_theta_max      37.4226

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91950
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            54281
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         37.57
_reflns_number_total             15966
_reflns_number_gt                9736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         15966
_refine_ls_number_parameters     509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1B S 0.92930(2) 0.28498(3) 0.52330(2) 0.01480(5) Uani 1 1 d . . .
S2B S 0.70302(3) 0.66459(3) 0.35426(2) 0.01921(6) Uani 1 1 d . . .
O1B O 0.94535(7) 0.29748(8) 0.62136(6) 0.01879(15) Uani 1 1 d . . .
O2B O 1.03554(6) 0.23134(8) 0.47453(6) 0.02009(16) Uani 1 1 d . . .
N1B N 0.86643(9) 0.44497(10) 0.24135(8) 0.0244(2) Uani 1 1 d . . .
N2B N 0.79299(8) 0.54010(9) 0.55423(7) 0.01785(18) Uani 1 1 d . . .
H2B H 0.8520(12) 0.4800(14) 0.5982(10) 0.024(3) Uiso 1 1 d . . .
C1B C 0.86347(9) 0.43830(10) 0.43091(8) 0.01550(19) Uani 1 1 d . . .
C2B C 0.79262(9) 0.53828(10) 0.45691(8) 0.01546(19) Uani 1 1 d . . .
C3B C 0.86530(9) 0.44508(10) 0.32504(8) 0.0169(2) Uani 1 1 d . . .
C4B C 0.71087(11) 0.80524(11) 0.37841(10) 0.0215(2) Uani 1 1 d . . .
H4BA H 0.6804(12) 0.8765(15) 0.3154(11) 0.028(4) Uiso 1 1 d . . .
H4BB H 0.7961(14) 0.8042(15) 0.3873(11) 0.035(4) Uiso 1 1 d . . .
H4BC H 0.6608(13) 0.8133(15) 0.4345(12) 0.032(4) Uiso 1 1 d . . .
C5B C 0.81456(9) 0.19244(10) 0.54314(8) 0.01530(19) Uani 1 1 d . . .
C6B C 0.70847(9) 0.21576(11) 0.60253(8) 0.01670(19) Uani 1 1 d . . .
H6B H 0.6987(12) 0.2789(14) 0.6346(11) 0.028(4) Uiso 1 1 d . . .
C7B C 0.61682(10) 0.14505(11) 0.61662(9) 0.0196(2) Uani 1 1 d . . .
H7B H 0.5434(12) 0.1597(14) 0.6569(11) 0.028(4) Uiso 1 1 d . . .
C8B C 0.63068(11) 0.05481(12) 0.57201(9) 0.0228(2) Uani 1 1 d . . .
H8B H 0.5691(14) 0.0077(15) 0.5815(12) 0.039(4) Uiso 1 1 d . . .
C9B C 0.73622(11) 0.03354(12) 0.51233(10) 0.0244(2) Uani 1 1 d . . .
H9B H 0.7471(13) -0.0321(15) 0.4842(11) 0.037(4) Uiso 1 1 d . . .
C10B C 0.82926(10) 0.10326(11) 0.49758(9) 0.0202(2) Uani 1 1 d . . .
H10B H 0.9026(13) 0.0861(14) 0.4600(11) 0.031(4) Uiso 1 1 d . . .
C11B C 0.68995(9) 0.59428(10) 0.60547(8) 0.01693(19) Uani 1 1 d . . .
C12B C 0.71238(11) 0.65829(11) 0.66573(9) 0.0208(2) Uani 1 1 d . . .
H12B H 0.7958(13) 0.6682(14) 0.6703(11) 0.030(4) Uiso 1 1 d . . .
C13B C 0.61510(12) 0.70391(13) 0.72165(10) 0.0261(2) Uani 1 1 d . . .
H13B H 0.6288(12) 0.7426(14) 0.7652(11) 0.026(4) Uiso 1 1 d . . .
C14B C 0.49609(11) 0.68669(13) 0.71583(10) 0.0284(3) Uani 1 1 d . . .
H14B H 0.4316(14) 0.7220(16) 0.7537(12) 0.044(4) Uiso 1 1 d . . .
C15B C 0.47449(11) 0.62202(13) 0.65614(10) 0.0280(3) Uani 1 1 d . . .
H15B H 0.3910(14) 0.6119(16) 0.6520(12) 0.045(4) Uiso 1 1 d . . .
C16B C 0.57125(10) 0.57472(12) 0.60102(9) 0.0224(2) Uani 1 1 d . . .
H16B H 0.5588(13) 0.5260(15) 0.5624(11) 0.032(4) Uiso 1 1 d . . .
O2A O 0.53922(7) 0.66519(8) 0.05897(7) 0.02388(17) Uani 1 1 d . . .
S1A S 0.42987(2) 0.72741(3) 0.09825(2) 0.01657(5) Uani 1 1 d . . .
S2A S 0.23968(3) 1.11864(3) -0.08511(2) 0.02049(6) Uani 1 1 d . . .
O1A O 0.43062(7) 0.73147(8) 0.20160(6) 0.01982(16) Uani 1 1 d . . .
N1A N 0.48669(10) 0.92886(11) -0.18053(8) 0.0321(3) Uani 1 1 d . . .
N2A N 0.26459(8) 0.96906(9) 0.12545(7) 0.01799(18) Uani 1 1 d . . .
H2A H 0.3124(12) 0.9108(14) 0.1736(11) 0.024(4) Uiso 1 1 d . . .
C1A C 0.38952(9) 0.88765(10) 0.00527(8) 0.0171(2) Uani 1 1 d . . .
C2A C 0.30082(9) 0.98220(10) 0.02596(8) 0.01636(19) Uani 1 1 d . . .
C3A C 0.44236(10) 0.91163(11) -0.09774(9) 0.0217(2) Uani 1 1 d . . .
C4A C 0.20668(11) 1.25006(11) -0.04100(10) 0.0214(2) Uani 1 1 d . . .
H4AA H 0.2139(12) 1.3239(15) -0.1053(11) 0.031(4) Uiso 1 1 d . . .
H4AB H 0.1246(12) 1.2583(13) -0.0095(10) 0.023(3) Uiso 1 1 d . . .
H4AC H 0.2684(13) 1.2363(14) 0.0064(11) 0.030(4) Uiso 1 1 d . . .
C5A C 0.30556(9) 0.65542(10) 0.09565(8) 0.01671(19) Uani 1 1 d . . .
C6A C 0.19938(10) 0.66996(11) 0.15737(9) 0.0189(2) Uani 1 1 d . . .
H6A H 0.1962(12) 0.7146(14) 0.2022(11) 0.028(4) Uiso 1 1 d . . .
C7A C 0.10091(10) 0.61568(12) 0.15204(10) 0.0233(2) Uani 1 1 d . . .
H7A H 0.0296(12) 0.6236(13) 0.1938(10) 0.023(3) Uiso 1 1 d . . .
C8A C 0.10902(11) 0.54884(13) 0.08729(10) 0.0266(3) Uani 1 1 d . . .
H8A H 0.0415(13) 0.5127(14) 0.0814(11) 0.031(4) Uiso 1 1 d . . .
C9A C 0.21495(12) 0.53588(13) 0.02546(10) 0.0269(2) Uani 1 1 d . . .
H9A H 0.2219(13) 0.4890(15) -0.0208(11) 0.034(4) Uiso 1 1 d . . .
C10A C 0.31432(11) 0.58956(12) 0.02963(9) 0.0227(2) Uani 1 1 d . . .
H10A H 0.3890(14) 0.5791(15) -0.0131(12) 0.038(4) Uiso 1 1 d . . .
C11A C 0.14914(9) 1.03267(10) 0.15597(8) 0.01650(19) Uani 1 1 d . . .
C12A C 0.15138(10) 1.10193(11) 0.21737(9) 0.0199(2) Uani 1 1 d . . .
H12A H 0.2313(12) 1.1031(13) 0.2400(10) 0.024(3) Uiso 1 1 d . . .
C13A C 0.04043(11) 1.16613(12) 0.24526(10) 0.0237(2) Uani 1 1 d . . .
H13A H 0.0404(12) 1.2130(15) 0.2864(11) 0.031(4) Uiso 1 1 d . . .
C14A C -0.07201(11) 1.16117(13) 0.21159(10) 0.0260(2) Uani 1 1 d . . .
H14A H -0.1500(13) 1.2126(15) 0.2261(11) 0.035(4) Uiso 1 1 d . . .
C15A C -0.07328(11) 1.08902(13) 0.15219(10) 0.0268(3) Uani 1 1 d . . .
H15A H -0.1526(14) 1.0900(15) 0.1278(12) 0.041(4) Uiso 1 1 d . . .
C16A C 0.03719(10) 1.02262(12) 0.12514(9) 0.0211(2) Uani 1 1 d . . .
H16A H 0.0350(12) 0.9695(14) 0.0875(11) 0.027(4) Uiso 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
S1B O2B 1.4369(8) . ?
S1B O1B 1.4469(8) . ?
S1B C1B 1.7522(11) . ?
S1B C5B 1.7681(10) . ?
S2B C2B 1.7531(11) . ?
S2B C4B 1.8072(12) . ?
N1B C3B 1.1517(14) . ?
N2B C2B 1.3492(14) . ?
N2B C11B 1.4358(14) . ?
N2B H2B 0.900(14) . ?
C1B C2B 1.3957(15) . ?
C1B C3B 1.4262(15) . ?
C4B H4BA 0.949(14) . ?
C4B H4BB 0.959(15) . ?
C4B H4BC 0.928(15) . ?
C5B C10B 1.3818(16) . ?
C5B C6B 1.3994(14) . ?
C6B C7B 1.3905(15) . ?
C6B H6B 0.978(15) . ?
C7B C8B 1.3842(17) . ?
C7B H7B 0.958(14) . ?
C8B C9B 1.3917(17) . ?
C8B H8B 0.931(15) . ?
C9B C10B 1.3940(16) . ?
C9B H9B 0.963(16) . ?
C10B H10B 0.943(14) . ?
C11B C12B 1.3848(16) . ?
C11B C16B 1.3913(15) . ?
C12B C13B 1.3904(17) . ?
C12B H12B 0.965(13) . ?
C13B C14B 1.3882(18) . ?
C13B H13B 0.921(14) . ?
C14B C15B 1.3813(19) . ?
C14B H14B 0.955(16) . ?
C15B C16B 1.3884(17) . ?
C15B H15B 0.966(15) . ?
C16B H16B 0.954(15) . ?
O2A S1A 1.4362(8) . ?
S1A O1A 1.4436(8) . ?
S1A C1A 1.7583(11) . ?
S1A C5A 1.7681(10) . ?
S2A C2A 1.7492(11) . ?
S2A C4A 1.8059(13) . ?
N1A C3A 1.1515(14) . ?
N2A C2A 1.3445(13) . ?
N2A C11A 1.4372(14) . ?
N2A H2A 0.850(14) . ?
C1A C2A 1.3967(15) . ?
C1A C3A 1.4198(15) . ?
C4A H4AA 0.960(15) . ?
C4A H4AB 0.967(13) . ?
C4A H4AC 0.935(14) . ?
C5A C10A 1.3873(16) . ?
C5A C6A 1.3973(15) . ?
C6A C7A 1.3936(15) . ?
C6A H6A 0.945(14) . ?
C7A C8A 1.3821(18) . ?
C7A H7A 0.938(13) . ?
C8A C9A 1.3928(18) . ?
C8A H8A 0.958(14) . ?
C9A C10A 1.3930(17) . ?
C9A H9A 0.978(15) . ?
C10A H10A 0.978(15) . ?
C11A C12A 1.3845(15) . ?
C11A C16A 1.3910(15) . ?
C12A C13A 1.3887(16) . ?
C12A H12A 0.970(13) . ?
C13A C14A 1.3901(17) . ?
C13A H13A 0.928(15) . ?
C14A C15A 1.3870(18) . ?
C14A H14A 0.983(15) . ?
C15A C16A 1.3917(17) . ?
C15A H15A 0.966(15) . ?
C16A H16A 0.956(14) . ?

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
O2B S1B O1B 118.89(5) . . ?
O2B S1B C1B 108.40(5) . . ?
O1B S1B C1B 107.73(5) . . ?
O2B S1B C5B 107.72(5) . . ?
O1B S1B C5B 108.96(5) . . ?
C1B S1B C5B 104.17(5) . . ?
C2B S2B C4B 102.84(5) . . ?
C2B N2B C11B 126.07(9) . . ?
C2B N2B H2B 115.3(9) . . ?
C11B N2B H2B 115.2(8) . . ?
C2B C1B C3B 120.49(9) . . ?
C2B C1B S1B 124.85(8) . . ?
C3B C1B S1B 113.40(8) . . ?
N2B C2B C1B 122.87(10) . . ?
N2B C2B S2B 121.22(8) . . ?
C1B C2B S2B 115.91(8) . . ?
N1B C3B C1B 177.02(11) . . ?
S2B C4B H4BA 104.7(9) . . ?
S2B C4B H4BB 108.7(9) . . ?
H4BA C4B H4BB 109.3(12) . . ?
S2B C4B H4BC 113.6(9) . . ?
H4BA C4B H4BC 107.8(12) . . ?
H4BB C4B H4BC 112.4(12) . . ?
C10B C5B C6B 121.91(10) . . ?
C10B C5B S1B 119.99(8) . . ?
C6B C5B S1B 118.07(8) . . ?
C7B C6B C5B 118.32(11) . . ?
C7B C6B H6B 120.2(8) . . ?
C5B C6B H6B 121.5(8) . . ?
C8B C7B C6B 120.38(10) . . ?
C8B C7B H7B 120.0(8) . . ?
C6B C7B H7B 119.6(9) . . ?
C7B C8B C9B 120.63(10) . . ?
C7B C8B H8B 120.2(10) . . ?
C9B C8B H8B 119.2(10) . . ?
C8B C9B C10B 119.81(11) . . ?
C8B C9B H9B 120.3(9) . . ?
C10B C9B H9B 119.9(9) . . ?
C5B C10B C9B 118.95(10) . . ?
C5B C10B H10B 121.1(9) . . ?
C9B C10B H10B 119.9(9) . . ?
C12B C11B C16B 120.54(10) . . ?
C12B C11B N2B 118.73(9) . . ?
C16B C11B N2B 120.56(10) . . ?
C11B C12B C13B 119.56(11) . . ?
C11B C12B H12B 119.6(9) . . ?
C13B C12B H12B 120.8(8) . . ?
C14B C13B C12B 120.06(12) . . ?
C14B C13B H13B 119.0(8) . . ?
C12B C13B H13B 120.9(8) . . ?
C15B C14B C13B 120.09(11) . . ?
C15B C14B H14B 122.7(9) . . ?
C13B C14B H14B 117.2(9) . . ?
C14B C15B C16B 120.31(11) . . ?
C14B C15B H15B 119.2(10) . . ?
C16B C15B H15B 120.5(10) . . ?
C15B C16B C11B 119.42(11) . . ?
C15B C16B H16B 121.4(8) . . ?
C11B C16B H16B 119.2(8) . . ?
O2A S1A O1A 119.88(5) . . ?
O2A S1A C1A 107.73(5) . . ?
O1A S1A C1A 107.49(5) . . ?
O2A S1A C5A 107.95(5) . . ?
O1A S1A C5A 108.16(5) . . ?
C1A S1A C5A 104.61(5) . . ?
C2A S2A C4A 104.95(5) . . ?
C2A N2A C11A 126.16(9) . . ?
C2A N2A H2A 114.5(9) . . ?
C11A N2A H2A 118.9(9) . . ?
C2A C1A C3A 121.27(10) . . ?
C2A C1A S1A 123.08(8) . . ?
C3A C1A S1A 115.24(8) . . ?
N2A C2A C1A 121.93(10) . . ?
N2A C2A S2A 121.98(8) . . ?
C1A C2A S2A 116.09(8) . . ?
N1A C3A C1A 178.72(14) . . ?
S2A C4A H4AA 103.0(9) . . ?
S2A C4A H4AB 111.5(8) . . ?
H4AA C4A H4AB 111.9(12) . . ?
S2A C4A H4AC 108.3(9) . . ?
H4AA C4A H4AC 109.9(12) . . ?
H4AB C4A H4AC 111.9(11) . . ?
C10A C5A C6A 121.66(10) . . ?
C10A C5A S1A 119.09(8) . . ?
C6A C5A S1A 119.22(9) . . ?
C7A C6A C5A 118.44(11) . . ?
C7A C6A H6A 121.6(8) . . ?
C5A C6A H6A 119.9(8) . . ?
C8A C7A C6A 120.41(11) . . ?
C8A C7A H7A 120.3(8) . . ?
C6A C7A H7A 119.3(8) . . ?
C7A C8A C9A 120.63(11) . . ?
C7A C8A H8A 121.5(9) . . ?
C9A C8A H8A 117.9(9) . . ?
C8A C9A C10A 119.80(12) . . ?
C8A C9A H9A 121.5(8) . . ?
C10A C9A H9A 118.7(8) . . ?
C5A C10A C9A 119.05(11) . . ?
C5A C10A H10A 121.4(9) . . ?
C9A C10A H10A 119.5(9) . . ?
C12A C11A C16A 120.91(10) . . ?
C12A C11A N2A 119.07(9) . . ?
C16A C11A N2A 120.01(10) . . ?
C11A C12A C13A 119.49(10) . . ?
C11A C12A H12A 118.3(8) . . ?
C13A C12A H12A 122.2(8) . . ?
C12A C13A C14A 120.27(11) . . ?
C12A C13A H13A 120.5(9) . . ?
C14A C13A H13A 119.2(9) . . ?
C15A C14A C13A 119.72(11) . . ?
C15A C14A H14A 120.0(9) . . ?
C13A C14A H14A 120.2(9) . . ?
C14A C15A C16A 120.54(11) . . ?
C14A C15A H15A 117.7(9) . . ?
C16A C15A H15A 121.7(9) . . ?
C11A C16A C15A 118.99(11) . . ?
C11A C16A H16A 121.2(8) . . ?
C15A C16A H16A 119.8(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
O2B S1B C1B C2B -154.46(8) . . . . ?
O1B S1B C1B C2B -24.60(10) . . . . ?
C5B S1B C1B C2B 91.03(9) . . . . ?
O2B S1B C1B C3B 38.39(9) . . . . ?
O1B S1B C1B C3B 168.25(7) . . . . ?
C5B S1B C1B C3B -76.12(8) . . . . ?
C11B N2B C2B C1B -147.36(10) . . . . ?
C11B N2B C2B S2B 33.46(14) . . . . ?
C3B C1B C2B N2B -176.21(9) . . . . ?
S1B C1B C2B N2B 17.50(14) . . . . ?
C3B C1B C2B S2B 3.02(13) . . . . ?
S1B C1B C2B S2B -163.28(6) . . . . ?
C4B S2B C2B N2B 35.28(9) . . . . ?
C4B S2B C2B C1B -143.96(8) . . . . ?
C2B C1B C3B N1B -138(2) . . . . ?
S1B C1B C3B N1B 30(2) . . . . ?
O2B S1B C5B C10B -10.44(10) . . . . ?
O1B S1B C5B C10B -140.69(9) . . . . ?
C1B S1B C5B C10B 104.55(9) . . . . ?
O2B S1B C5B C6B 171.67(8) . . . . ?
O1B S1B C5B C6B 41.42(10) . . . . ?
C1B S1B C5B C6B -73.34(9) . . . . ?
C10B C5B C6B C7B 0.91(16) . . . . ?
S1B C5B C6B C7B 178.75(8) . . . . ?
C5B C6B C7B C8B -0.48(16) . . . . ?
C6B C7B C8B C9B -0.10(18) . . . . ?
C7B C8B C9B C10B 0.28(18) . . . . ?
C6B C5B C10B C9B -0.74(17) . . . . ?
S1B C5B C10B C9B -178.54(9) . . . . ?
C8B C9B C10B C5B 0.14(18) . . . . ?
C2B N2B C11B C12B -142.03(11) . . . . ?
C2B N2B C11B C16B 42.59(16) . . . . ?
C16B C11B C12B C13B -0.37(17) . . . . ?
N2B C11B C12B C13B -175.75(10) . . . . ?
C11B C12B C13B C14B -0.82(18) . . . . ?
C12B C13B C14B C15B 1.3(2) . . . . ?
C13B C14B C15B C16B -0.5(2) . . . . ?
C14B C15B C16B C11B -0.71(19) . . . . ?
C12B C11B C16B C15B 1.14(18) . . . . ?
N2B C11B C16B C15B 176.43(11) . . . . ?
O2A S1A C1A C2A -168.76(9) . . . . ?
O1A S1A C1A C2A -38.28(10) . . . . ?
C5A S1A C1A C2A 76.55(10) . . . . ?
O2A S1A C1A C3A 18.51(10) . . . . ?
O1A S1A C1A C3A 148.99(8) . . . . ?
C5A S1A C1A C3A -96.19(9) . . . . ?
C11A N2A C2A C1A -156.88(10) . . . . ?
C11A N2A C2A S2A 23.12(15) . . . . ?
C3A C1A C2A N2A -169.16(10) . . . . ?
S1A C1A C2A N2A 18.53(15) . . . . ?
C3A C1A C2A S2A 10.84(14) . . . . ?
S1A C1A C2A S2A -161.47(6) . . . . ?
C4A S2A C2A N2A 32.13(10) . . . . ?
C4A S2A C2A C1A -147.87(8) . . . . ?
C2A C1A C3A N1A 175(100) . . . . ?
S1A C1A C3A N1A -12(6) . . . . ?
O2A S1A C5A C10A -20.89(11) . . . . ?
O1A S1A C5A C10A -152.00(9) . . . . ?
C1A S1A C5A C10A 93.65(10) . . . . ?
O2A S1A C5A C6A 161.23(9) . . . . ?
O1A S1A C5A C6A 30.12(10) . . . . ?
C1A S1A C5A C6A -84.23(10) . . . . ?
C10A C5A C6A C7A 0.39(17) . . . . ?
S1A C5A C6A C7A 178.21(9) . . . . ?
C5A C6A C7A C8A 0.21(17) . . . . ?
C6A C7A C8A C9A -0.74(19) . . . . ?
C7A C8A C9A C10A 0.7(2) . . . . ?
C6A C5A C10A C9A -0.45(18) . . . . ?
S1A C5A C10A C9A -178.27(9) . . . . ?
C8A C9A C10A C5A -0.09(19) . . . . ?
C2A N2A C11A C12A -126.51(12) . . . . ?
C2A N2A C11A C16A 54.41(15) . . . . ?
C16A C11A C12A C13A -2.36(17) . . . . ?
N2A C11A C12A C13A 178.56(10) . . . . ?
C11A C12A C13A C14A -0.16(18) . . . . ?
C12A C13A C14A C15A 1.65(19) . . . . ?
C13A C14A C15A C16A -0.6(2) . . . . ?
C12A C11A C16A C15A 3.34(17) . . . . ?
N2A C11A C16A C15A -177.59(10) . . . . ?
C14A C15A C16A C11A -1.82(19) . . . . ?

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
N2A H2A O1A 0.850(14) 2.095(14) 2.7931(13) 139.1(12) .
N2B H2B O1B 0.900(14) 2.040(14) 2.7654(12) 136.8(12) .

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        35.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.068


