# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_compound1b
_database_code_depnum_ccdc_archive 'CCDC 1405545'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N2 S6'
_chemical_formula_sum            'C14 H18 N2 S6'
_chemical_formula_weight         406.72

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4366(4)
_cell_length_b                   7.0950(7)
_cell_length_c                   14.0927(14)
_cell_angle_alpha                91.198(3)
_cell_angle_beta                 95.948(2)
_cell_angle_gamma                97.185(2)
_cell_volume                     437.49(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5581
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.66


_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_T_max  0.856

#----------------------------- Remark ------------------------------#
# Tmax and Tmin values correspond to EXPECTED values calculated     #
# from crystal size. In the case of absorption correction performed #
# with SADABS program, Tmax should be given as Tmax_expected and    #
# and Tmin = Tmax * 'relative-correction-factor'.                   #
# SADABS output:                                                    #
# Ratio of minimum to maximum apparent transmission:  0.834971      #
#-------------------------------------------------------------------#


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7360
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.66
_reflns_number_total             2008
_reflns_number_gt                1927
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0459P)²+0.1002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2008
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0673
_refine_ls_goodness_of_fit_ref   1.269
_refine_ls_restrained_S_all      1.269
_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 0.55850(7) 0.26517(5) 0.58981(2) 0.01302(12) Uani 1 1 d . . .
S2 S 0.32634(9) 0.37343(5) 0.77094(3) 0.02003(13) Uani 1 1 d . . .
S3 S 0.10452(8) -0.30025(5) 0.57928(3) 0.01598(12) Uani 1 1 d . . .
N1 N 0.1883(3) 0.03376(16) 0.67664(8) 0.0132(3) Uani 1 1 d . . .
C1 C 0.4524(3) 0.03481(19) 0.54104(9) 0.0119(3) Uani 1 1 d . . .
C2 C 0.2468(3) -0.0760(2) 0.60001(10) 0.0126(3) Uani 1 1 d . . .
C3 C 0.3385(3) 0.2158(2) 0.68538(10) 0.0139(3) Uani 1 1 d . . .
C4 C 0.0003(3) -0.0449(2) 0.75012(10) 0.0152(3) Uani 1 1 d . . .
H4A H -0.1558 -0.1434 0.7214 0.018 Uiso 1 1 calc R . .
H4B H -0.1007 0.0546 0.7766 0.018 Uiso 1 1 calc R . .
C5 C 0.1980(3) -0.1278(2) 0.82963(10) 0.0143(3) Uani 1 1 d . . .
H5A H 0.3546 -0.0289 0.8576 0.017 Uiso 1 1 calc R . .
H5B H 0.2992 -0.2267 0.8026 0.017 Uiso 1 1 calc R . .
C6 C 0.0128(3) -0.2111(2) 0.90774(10) 0.0165(3) Uani 1 1 d . . .
H6A H -0.1322 -0.3173 0.8809 0.020 Uiso 1 1 calc R . .
H6B H -0.1019 -0.1154 0.9312 0.020 Uiso 1 1 calc R . .
C7 C 0.2160(4) -0.2787(2) 0.99094(11) 0.0197(3) Uani 1 1 d . . .
H7A H 0.0913 -0.3301 1.0384 0.029 Uiso 1 1 calc R . .
H7B H 0.3571 -0.1734 1.0185 0.029 Uiso 1 1 calc R . .
H7C H 0.3272 -0.3751 0.9683 0.029 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7489(14) . ?
S1 C3 1.7595(15) . ?
S2 C3 1.6372(15) . ?
S3 C2 1.6450(14) . ?
N1 C3 1.3741(18) . ?
N1 C2 1.3834(18) . ?
N1 C4 1.4716(18) . ?
C1 C1 1.375(3) 2_656 ?
C1 C2 1.4651(19) . ?
C4 C5 1.5245(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5260(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.526(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C3 91.43(7) . . ?
C3 N1 C2 116.24(12) . . ?
C3 N1 C4 121.45(12) . . ?
C2 N1 C4 122.04(12) . . ?
C1 C1 C2 124.10(16) 2_656 . ?
C1 C1 S1 125.26(14) 2_656 . ?
C2 C1 S1 110.64(10) . . ?
N1 C2 C1 110.62(12) . . ?
N1 C2 S3 124.15(11) . . ?
C1 C2 S3 125.22(11) . . ?
N1 C3 S2 127.02(11) . . ?
N1 C3 S1 111.00(10) . . ?
S2 C3 S1 121.98(9) . . ?
N1 C4 C5 110.51(11) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 112.44(12) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 112.03(12) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S1 C1 C1 -179.66(17) . . . 2_656 ?
C3 S1 C1 C2 0.19(10) . . . . ?
C3 N1 C2 C1 -2.83(16) . . . . ?
C4 N1 C2 C1 -176.91(11) . . . . ?
C3 N1 C2 S3 176.91(10) . . . . ?
C4 N1 C2 S3 2.82(18) . . . . ?
C1 C1 C2 N1 -178.77(16) 2_656 . . . ?
S1 C1 C2 N1 1.37(14) . . . . ?
C1 C1 C2 S3 1.5(2) 2_656 . . . ?
S1 C1 C2 S3 -178.36(8) . . . . ?
C2 N1 C3 S2 -176.98(10) . . . . ?
C4 N1 C3 S2 -2.85(19) . . . . ?
C2 N1 C3 S1 2.98(15) . . . . ?
C4 N1 C3 S1 177.10(9) . . . . ?
C1 S1 C3 N1 -1.72(10) . . . . ?
C1 S1 C3 S2 178.24(9) . . . . ?
C3 N1 C4 C5 -85.34(15) . . . . ?
C2 N1 C4 C5 88.44(15) . . . . ?
N1 C4 C5 C6 179.93(11) . . . . ?
C4 C5 C6 C7 -175.22(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.153
####################################################################### 
# 
# 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_compound1c
_database_code_depnum_ccdc_archive 'CCDC 1405546'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2015-04-14T10:57:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H10 N2 S6'
_chemical_formula_sum            'C18 H10 N2 S6'
_chemical_formula_weight         446.64
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.369(3)
_cell_length_b                   10.336(2)
_cell_length_c                   21.421(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1853.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1769
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      26.56
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.415
_exptl_absorpt_correction_T_max  0.935


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_number            6804
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.956
_reflns_number_total             2018
_reflns_number_gt                1511
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0410P)²+4.2618P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.11

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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
C1 C 0.7681(5) 0.1728(4) 0.43501(19) 0.0184(8) Uani 1 1 d . . .
N2 N 0.6226(4) 0.1859(3) 0.40529(16) 0.0186(7) Uani 1 1 d . . .
C3 C 0.4968(5) 0.1154(4) 0.42954(18) 0.0165(8) Uani 1 1 d . . .
C4 C 0.5491(5) 0.0393(4) 0.48293(18) 0.0155(8) Uani 1 1 d . . .
C5 C 0.6056(5) 0.2687(4) 0.35177(19) 0.0185(9) Uani 1 1 d . . .
C6 C 0.6627(5) 0.2270(4) 0.2951(2) 0.0222(9) Uani 1 1 d . . .
H6 H 0.7128 0.1449 0.2915 0.027 Uiso 1 1 calc R . .
C7 C 0.6463(6) 0.3063(4) 0.2434(2) 0.0280(10) Uani 1 1 d . . .
H7 H 0.6849 0.2788 0.2039 0.034 Uiso 1 1 calc R . .
C8 C 0.5728(6) 0.4267(4) 0.2497(2) 0.0266(10) Uani 1 1 d . . .
H8 H 0.5618 0.4815 0.2143 0.032 Uiso 1 1 calc R . .
C9 C 0.5162(6) 0.4666(4) 0.3067(2) 0.0254(10) Uani 1 1 d . . .
H9 H 0.4656 0.5485 0.3106 0.03 Uiso 1 1 calc R . .
C10 C 0.5325(5) 0.3877(4) 0.3588(2) 0.0215(9) Uani 1 1 d . . .
H10 H 0.4943 0.415 0.3985 0.026 Uiso 1 1 calc R . .
S1 S 0.75237(13) 0.06282(11) 0.49689(5) 0.0192(3) Uani 1 1 d . . .
S2 S 0.93526(13) 0.24362(11) 0.41766(5) 0.0236(3) Uani 1 1 d . . .
S3 S 0.31538(13) 0.11625(11) 0.40151(5) 0.0242(3) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N2 1.381(5) . ?
C1 S2 1.622(4) . ?
C1 S1 1.751(4) . ?
N2 C3 1.382(5) . ?
N2 C5 1.438(5) . ?
C3 C4 1.456(5) . ?
C3 S3 1.633(4) . ?
C4 C4 1.368(8) 5_656 ?
C4 S1 1.744(4) . ?
C5 C6 1.374(6) . ?
C5 C10 1.382(6) . ?
C6 C7 1.385(6) . ?
C6 H6 0.95 . ?
C7 C8 1.395(6) . ?
C7 H7 0.95 . ?
C8 C9 1.374(6) . ?
C8 H8 0.95 . ?
C9 C10 1.388(6) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?


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
N2 C1 S2 127.6(3) . . ?
N2 C1 S1 110.2(3) . . ?
S2 C1 S1 122.1(2) . . ?
C1 N2 C3 116.6(3) . . ?
C1 N2 C5 120.9(3) . . ?
C3 N2 C5 122.5(3) . . ?
N2 C3 C4 110.6(3) . . ?
N2 C3 S3 124.6(3) . . ?
C4 C3 S3 124.9(3) . . ?
C4 C4 C3 124.1(5) 5_656 . ?
C4 C4 S1 125.3(4) 5_656 . ?
C3 C4 S1 110.7(3) . . ?
C6 C5 C10 122.0(4) . . ?
C6 C5 N2 118.9(4) . . ?
C10 C5 N2 119.1(4) . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C8 119.6(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C9 118.6(4) . . ?
C5 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C4 S1 C1 91.97(19) . . ?


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
S2 C1 N2 C3 -179.5(3) . . . . ?
S1 C1 N2 C3 1.3(4) . . . . ?
S2 C1 N2 C5 0.8(6) . . . . ?
S1 C1 N2 C5 -178.5(3) . . . . ?
C1 N2 C3 C4 -0.5(5) . . . . ?
C5 N2 C3 C4 179.3(3) . . . . ?
C1 N2 C3 S3 -179.8(3) . . . . ?
C5 N2 C3 S3 0.0(6) . . . . ?
N2 C3 C4 C4 179.3(5) . . . 5_656 ?
S3 C3 C4 C4 -1.4(7) . . . 5_656 ?
N2 C3 C4 S1 -0.6(4) . . . . ?
S3 C3 C4 S1 178.7(2) . . . . ?
C1 N2 C5 C6 76.3(5) . . . . ?
C3 N2 C5 C6 -103.5(5) . . . . ?
C1 N2 C5 C10 -103.7(5) . . . . ?
C3 N2 C5 C10 76.6(5) . . . . ?
C10 C5 C6 C7 -0.2(7) . . . . ?
N2 C5 C6 C7 179.9(4) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C6 C7 C8 C9 -0.3(7) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?
C6 C5 C10 C9 0.3(6) . . . . ?
N2 C5 C10 C9 -179.7(4) . . . . ?
C8 C9 C10 C5 -0.4(7) . . . . ?
C4 C4 S1 C1 -178.8(5) 5_656 . . . ?
C3 C4 S1 C1 1.1(3) . . . . ?
N2 C1 S1 C4 -1.4(3) . . . . ?
S2 C1 S1 C4 179.4(3) . . . . ?


#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR Y378                                                 #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# 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_compound1d
_database_code_depnum_ccdc_archive 'CCDC 1405547'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2010-05-27T17:12:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N2 O2 S4'
_chemical_formula_sum            'C10 H10 N2 O2 S4'
_chemical_formula_weight         318.44
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a b'
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   6.8237(5)
_cell_length_b                   8.5474(7)
_cell_length_c                   22.3448(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1303.26(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1338
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      27.32
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.979


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_number            5672
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             1482
_reflns_number_gt                1075
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0364P)²+0.0648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1482
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.78288(7) 0.37415(6) 0.49700(2) 0.02005(16) Uani 1 1 d . . .
S2 S 0.39640(9) 0.63009(7) 0.38388(3) 0.02842(18) Uani 1 1 d . . .
C1 C 0.8625(3) 0.3867(3) 0.42144(10) 0.0208(5) Uani 1 1 d . . .
O2 O 1.0094(2) 0.32623(18) 0.40213(7) 0.0291(4) Uani 1 1 d . . .
N3 N 0.7344(2) 0.4758(2) 0.38748(7) 0.0175(4) Uani 1 1 d . . .
C4 C 0.7736(3) 0.4994(3) 0.32362(9) 0.0238(5) Uani 1 1 d . . .
H4A H 0.917 0.4992 0.3168 0.029 Uiso 1 1 calc R . .
H4B H 0.7223 0.6028 0.3113 0.029 Uiso 1 1 calc R . .
C5 C 0.6800(3) 0.3735(3) 0.28546(10) 0.0313(6) Uani 1 1 d . . .
H5A H 0.7229 0.2704 0.2995 0.047 Uiso 1 1 calc R . .
H5B H 0.7196 0.3876 0.2436 0.047 Uiso 1 1 calc R . .
H5C H 0.5371 0.381 0.2886 0.047 Uiso 1 1 calc R . .
C6 C 0.5701(3) 0.5284(2) 0.41649(9) 0.0174(5) Uani 1 1 d . . .
C7 C 0.5722(3) 0.4817(2) 0.47993(9) 0.0162(4) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.749(2) . ?
S1 C1 1.777(2) . ?
S2 C6 1.641(2) . ?
C1 O2 1.207(2) . ?
C1 N3 1.385(3) . ?
N3 C6 1.371(2) . ?
N3 C4 1.466(3) . ?
C4 C5 1.514(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C7 1.473(3) . ?
C7 C7 1.368(4) 5_666 ?


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
C7 S1 C1 90.71(10) . . ?
O2 C1 N3 124.3(2) . . ?
O2 C1 S1 124.57(17) . . ?
N3 C1 S1 111.15(15) . . ?
C6 N3 C1 115.92(17) . . ?
C6 N3 C4 124.36(17) . . ?
C1 N3 C4 119.59(17) . . ?
N3 C4 C5 111.93(18) . . ?
N3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 111.01(17) . . ?
N3 C6 S2 123.69(16) . . ?
C7 C6 S2 125.30(15) . . ?
C7 C7 C6 124.2(2) 5_666 . ?
C7 C7 S1 124.7(2) 5_666 . ?
C6 C7 S1 111.11(14) . . ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 S1 C1 O2 -177.6(2) . . . . ?
C7 S1 C1 N3 2.71(15) . . . . ?
O2 C1 N3 C6 176.8(2) . . . . ?
S1 C1 N3 C6 -3.5(2) . . . . ?
O2 C1 N3 C4 0.7(3) . . . . ?
S1 C1 N3 C4 -179.59(15) . . . . ?
C6 N3 C4 C5 -85.8(2) . . . . ?
C1 N3 C4 C5 90.0(2) . . . . ?
C1 N3 C6 C7 2.4(2) . . . . ?
C4 N3 C6 C7 178.31(18) . . . . ?
C1 N3 C6 S2 -177.70(15) . . . . ?
C4 N3 C6 S2 -1.8(3) . . . . ?
N3 C6 C7 C7 179.7(2) . . . 5_666 ?
S2 C6 C7 C7 -0.2(4) . . . 5_666 ?
N3 C6 C7 S1 -0.2(2) . . . . ?
S2 C6 C7 S1 179.89(12) . . . . ?
C1 S1 C7 C7 178.7(3) . . . 5_666 ?
C1 S1 C7 C6 -1.40(15) . . . . ?


####################################################################### 
# 
# 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_compound5a
_database_code_depnum_ccdc_archive 'CCDC 1405548'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2014-02-28T15:36:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H15 N1 S4 Ti1'
_chemical_formula_sum            'C15 H15 N S4 Ti'
_chemical_formula_weight         385.42
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.8293(5)
_cell_length_b                   10.1390(5)
_cell_length_c                   15.9153(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1586.11(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2874
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.46
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_T_max  0.853


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_number            6413
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             2792
_reflns_number_gt                2692
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0588P)²+0.8588P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2792
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   0.722
_refine_ls_restrained_S_all      0.722
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.003
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.058

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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
C1 C 0.5442(3) 0.9309(3) 0.41850(19) 0.0201(6) Uani 1 1 d . . .
H1 H 0.6382 0.9525 0.4214 0.024 Uiso 1 1 calc R . .
C2 C 0.4342(3) 1.0183(3) 0.43466(19) 0.0215(6) Uani 1 1 d . . .
H2 H 0.4419 1.1086 0.4497 0.026 Uiso 1 1 calc R . .
C3 C 0.3122(3) 0.9478(3) 0.42452(18) 0.0231(6) Uani 1 1 d . . .
H3 H 0.223 0.9822 0.4316 0.028 Uiso 1 1 calc R . .
C4 C 0.3452(3) 0.8181(3) 0.40213(18) 0.0237(6) Uani 1 1 d . . .
H4 H 0.2819 0.7491 0.3918 0.028 Uiso 1 1 calc R . .
C5 C 0.4896(3) 0.8066(3) 0.39740(18) 0.0221(6) Uani 1 1 d . . .
H5 H 0.5396 0.7298 0.3828 0.026 Uiso 1 1 calc R . .
C6 C 0.6424(3) 1.0300(3) 0.2505(2) 0.0268(7) Uani 1 1 d . . .
H6 H 0.7195 0.9848 0.2722 0.032 Uiso 1 1 calc R . .
C7 C 0.5770(3) 1.1389(3) 0.2882(2) 0.0261(6) Uani 1 1 d . . .
H7 H 0.6037 1.1818 0.3386 0.031 Uiso 1 1 calc R . .
C8 C 0.4655(3) 1.1722(3) 0.23779(19) 0.0255(6) Uani 1 1 d . . .
H8 H 0.4012 1.2399 0.2491 0.031 Uiso 1 1 calc R . .
C9 C 0.4651(3) 1.0881(3) 0.1676(2) 0.0238(6) Uani 1 1 d . . .
H9 H 0.4017 1.0906 0.1226 0.029 Uiso 1 1 calc R . .
C10 C 0.5739(3) 1.0000(3) 0.1755(2) 0.0257(7) Uani 1 1 d . . .
H10 H 0.5972 0.9322 0.1369 0.031 Uiso 1 1 calc R . .
C11 C 0.2051(2) 0.9317(3) 0.15798(17) 0.0147(5) Uani 1 1 d . . .
C12 C 0.2906(3) 0.8268(3) 0.14135(18) 0.0178(5) Uani 1 1 d . . .
C13 C 0.1569(2) 0.9037(3) 0.01532(17) 0.0166(5) Uani 1 1 d . . .
C14 C 0.0511(2) 1.0956(3) 0.08528(18) 0.0162(5) Uani 1 1 d . . .
H14A H 0.0538 1.1358 0.0286 0.019 Uiso 1 1 calc R . .
H14B H 0.0885 1.1605 0.1256 0.019 Uiso 1 1 calc R . .
C15 C -0.0952(3) 1.0658(3) 0.1083(2) 0.0202(6) Uani 1 1 d . . .
H15A H -0.131 0.9977 0.0706 0.03 Uiso 1 1 calc R . .
H15B H -0.1499 1.1461 0.1028 0.03 Uiso 1 1 calc R . .
H15C H -0.0993 1.0342 0.1665 0.03 Uiso 1 1 calc R . .
N1 N 0.1370(2) 0.9757(2) 0.08594(15) 0.0147(4) Uani 1 1 d . . .
S1 S 0.18390(6) 1.00008(7) 0.25611(5) 0.01773(13) Uani 1 1 d . . .
S2 S 0.39439(7) 0.75276(7) 0.21448(5) 0.02045(15) Uani 1 1 d . . .
S3 S 0.27752(6) 0.78195(6) 0.03596(4) 0.01956(15) Uani 1 1 d . . .
S4 S 0.08435(7) 0.92480(8) -0.07859(5) 0.02189(16) Uani 1 1 d . . .
Ti1 Ti 0.42269(4) 0.95794(4) 0.29136(3) 0.01250(11) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C5 1.410(4) . ?
C1 C2 1.421(4) . ?
C1 Ti1 2.366(3) . ?
C1 H1 0.95 . ?
C2 C3 1.406(4) . ?
C2 Ti1 2.364(3) . ?
C2 H2 0.95 . ?
C3 C4 1.401(4) . ?
C3 Ti1 2.384(3) . ?
C3 H3 0.95 . ?
C4 C5 1.427(4) . ?
C4 Ti1 2.387(3) . ?
C4 H4 0.95 . ?
C5 Ti1 2.374(3) . ?
C5 H5 0.95 . ?
C6 C10 1.405(5) . ?
C6 C7 1.412(4) . ?
C6 Ti1 2.371(3) . ?
C6 H6 0.95 . ?
C7 C8 1.399(4) . ?
C7 Ti1 2.381(3) . ?
C7 H7 0.95 . ?
C8 C9 1.405(4) . ?
C8 Ti1 2.371(3) . ?
C8 H8 0.95 . ?
C9 C10 1.399(4) . ?
C9 Ti1 2.407(3) . ?
C9 H9 0.95 . ?
C10 Ti1 2.407(3) . ?
C10 H10 0.95 . ?
C11 C12 1.381(4) . ?
C11 N1 1.401(3) . ?
C11 S1 1.721(3) . ?
C12 S2 1.720(3) . ?
C12 S3 1.743(3) . ?
C13 N1 1.354(4) . ?
C13 S4 1.670(3) . ?
C13 S3 1.742(3) . ?
C14 N1 1.480(3) . ?
C14 C15 1.514(3) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
S1 Ti1 2.4508(7) . ?
S2 Ti1 2.4295(8) . ?


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 108.1(2) . . ?
C5 C1 Ti1 73.00(16) . . ?
C2 C1 Ti1 72.45(16) . . ?
C5 C1 H1 126 . . ?
C2 C1 H1 126 . . ?
Ti1 C1 H1 120.4 . . ?
C3 C2 C1 108.2(3) . . ?
C3 C2 Ti1 73.55(17) . . ?
C1 C2 Ti1 72.58(17) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Ti1 C2 H2 119.8 . . ?
C4 C3 C2 108.0(2) . . ?
C4 C3 Ti1 73.07(16) . . ?
C2 C3 Ti1 72.01(16) . . ?
C4 C3 H3 126 . . ?
C2 C3 H3 126 . . ?
Ti1 C3 H3 120.7 . . ?
C3 C4 C5 108.7(2) . . ?
C3 C4 Ti1 72.77(15) . . ?
C5 C4 Ti1 72.04(15) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Ti1 C4 H4 121.2 . . ?
C1 C5 C4 107.1(2) . . ?
C1 C5 Ti1 72.38(16) . . ?
C4 C5 Ti1 73.09(15) . . ?
C1 C5 H5 126.5 . . ?
C4 C5 H5 126.5 . . ?
Ti1 C5 H5 120 . . ?
C10 C6 C7 108.1(3) . . ?
C10 C6 Ti1 74.30(16) . . ?
C7 C6 Ti1 73.10(15) . . ?
C10 C6 H6 125.9 . . ?
C7 C6 H6 125.9 . . ?
Ti1 C6 H6 118.6 . . ?
C8 C7 C6 107.6(3) . . ?
C8 C7 Ti1 72.51(15) . . ?
C6 C7 Ti1 72.33(15) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
Ti1 C7 H7 120.8 . . ?
C9 C8 C7 108.1(3) . . ?
C9 C8 Ti1 74.29(16) . . ?
C7 C8 Ti1 73.24(16) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
Ti1 C8 H8 118.4 . . ?
C8 C9 C10 108.3(3) . . ?
C8 C9 Ti1 71.51(17) . . ?
C10 C9 Ti1 73.10(17) . . ?
C8 C9 H9 125.8 . . ?
C10 C9 H9 125.8 . . ?
Ti1 C9 H9 121.3 . . ?
C6 C10 C9 107.8(3) . . ?
C6 C10 Ti1 71.50(17) . . ?
C9 C10 Ti1 73.12(17) . . ?
C6 C10 H10 126.1 . . ?
C9 C10 H10 126.1 . . ?
Ti1 C10 H10 121 . . ?
C12 C11 N1 112.3(2) . . ?
C12 C11 S1 123.9(2) . . ?
N1 C11 S1 123.83(19) . . ?
C11 C12 S2 124.6(2) . . ?
C11 C12 S3 109.9(2) . . ?
S2 C12 S3 125.55(16) . . ?
N1 C13 S4 127.7(2) . . ?
N1 C13 S3 108.89(19) . . ?
S4 C13 S3 123.38(16) . . ?
N1 C14 C15 112.1(2) . . ?
N1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 N1 C11 116.0(2) . . ?
C13 N1 C14 121.3(2) . . ?
C11 N1 C14 122.7(2) . . ?
C11 S1 Ti1 91.23(8) . . ?
C12 S2 Ti1 92.01(10) . . ?
C12 S3 C13 92.69(13) . . ?
C1 Ti1 C2 34.97(10) . . ?
C1 Ti1 C8 108.91(10) . . ?
C2 Ti1 C8 95.81(11) . . ?
C1 Ti1 C5 34.62(10) . . ?
C2 Ti1 C5 57.87(11) . . ?
C8 Ti1 C5 142.99(10) . . ?
C1 Ti1 C6 79.05(11) . . ?
C2 Ti1 C6 98.11(12) . . ?
C8 Ti1 C6 57.16(10) . . ?
C5 Ti1 C6 98.13(11) . . ?
C1 Ti1 C3 57.64(10) . . ?
C2 Ti1 C3 34.44(10) . . ?
C8 Ti1 C3 116.10(11) . . ?
C5 Ti1 C3 57.76(10) . . ?
C6 Ti1 C3 132.24(11) . . ?
C1 Ti1 C7 77.63(11) . . ?
C2 Ti1 C7 77.91(11) . . ?
C8 Ti1 C7 34.25(11) . . ?
C5 Ti1 C7 109.68(11) . . ?
C6 Ti1 C7 34.57(11) . . ?
C3 Ti1 C7 110.02(11) . . ?
C1 Ti1 C4 57.37(10) . . ?
C2 Ti1 C4 57.09(11) . . ?
C8 Ti1 C4 150.03(11) . . ?
C5 Ti1 C4 34.87(9) . . ?
C6 Ti1 C4 132.54(11) . . ?
C3 Ti1 C4 34.16(11) . . ?
C7 Ti1 C4 132.60(11) . . ?
C1 Ti1 C9 132.53(10) . . ?
C2 Ti1 C9 129.73(11) . . ?
C8 Ti1 C9 34.19(10) . . ?
C5 Ti1 C9 152.63(10) . . ?
C6 Ti1 C9 56.58(11) . . ?
C3 Ti1 C9 146.09(11) . . ?
C7 Ti1 C9 56.62(11) . . ?
C4 Ti1 C9 170.09(10) . . ?
C1 Ti1 C10 111.36(11) . . ?
C2 Ti1 C10 131.60(11) . . ?
C8 Ti1 C10 56.80(11) . . ?
C5 Ti1 C10 119.23(11) . . ?
C6 Ti1 C10 34.19(11) . . ?
C3 Ti1 C10 166.03(11) . . ?
C7 Ti1 C10 56.89(11) . . ?
C4 Ti1 C10 150.26(11) . . ?
C9 Ti1 C10 33.78(11) . . ?
C1 Ti1 S2 112.92(7) . . ?
C2 Ti1 S2 135.48(8) . . ?
C8 Ti1 S2 128.59(8) . . ?
C5 Ti1 S2 80.58(8) . . ?
C6 Ti1 S2 103.30(8) . . ?
C3 Ti1 S2 111.02(8) . . ?
C7 Ti1 S2 136.23(8) . . ?
C4 Ti1 S2 80.02(8) . . ?
C9 Ti1 S2 94.43(8) . . ?
C10 Ti1 S2 80.59(8) . . ?
C1 Ti1 S1 134.40(7) . . ?
C2 Ti1 S1 102.81(7) . . ?
C8 Ti1 S1 85.86(8) . . ?
C5 Ti1 S1 122.74(7) . . ?
C6 Ti1 S1 139.12(8) . . ?
C3 Ti1 S1 76.97(7) . . ?
C7 Ti1 S1 118.09(8) . . ?
C4 Ti1 S1 88.10(7) . . ?
C9 Ti1 S1 83.27(7) . . ?
C10 Ti1 S1 112.64(8) . . ?
S2 Ti1 S1 85.66(3) . . ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 0.7(3) . . . . ?
Ti1 C1 C2 C3 65.5(2) . . . . ?
C5 C1 C2 Ti1 -64.8(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
Ti1 C2 C3 C4 64.7(2) . . . . ?
C1 C2 C3 Ti1 -64.8(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
Ti1 C3 C4 C5 63.54(19) . . . . ?
C2 C3 C4 Ti1 -64.0(2) . . . . ?
C2 C1 C5 C4 -0.9(3) . . . . ?
Ti1 C1 C5 C4 -65.37(19) . . . . ?
C2 C1 C5 Ti1 64.4(2) . . . . ?
C3 C4 C5 C1 0.9(3) . . . . ?
Ti1 C4 C5 C1 64.9(2) . . . . ?
C3 C4 C5 Ti1 -64.0(2) . . . . ?
C10 C6 C7 C8 2.2(3) . . . . ?
Ti1 C6 C7 C8 -64.40(19) . . . . ?
C10 C6 C7 Ti1 66.6(2) . . . . ?
C6 C7 C8 C9 -2.4(3) . . . . ?
Ti1 C7 C8 C9 -66.7(2) . . . . ?
C6 C7 C8 Ti1 64.3(2) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
Ti1 C8 C9 C10 -64.3(2) . . . . ?
C7 C8 C9 Ti1 65.97(19) . . . . ?
C7 C6 C10 C9 -1.2(3) . . . . ?
Ti1 C6 C10 C9 64.6(2) . . . . ?
C7 C6 C10 Ti1 -65.8(2) . . . . ?
C8 C9 C10 C6 -0.3(3) . . . . ?
Ti1 C9 C10 C6 -63.6(2) . . . . ?
C8 C9 C10 Ti1 63.3(2) . . . . ?
N1 C11 C12 S2 177.40(18) . . . . ?
S1 C11 C12 S2 -3.0(3) . . . . ?
N1 C11 C12 S3 -2.4(3) . . . . ?
S1 C11 C12 S3 177.21(15) . . . . ?
S4 C13 N1 C11 176.30(19) . . . . ?
S3 C13 N1 C11 -5.1(3) . . . . ?
S4 C13 N1 C14 -5.3(3) . . . . ?
S3 C13 N1 C14 173.29(18) . . . . ?
C12 C11 N1 C13 5.0(3) . . . . ?
S1 C11 N1 C13 -174.61(19) . . . . ?
C12 C11 N1 C14 -173.3(2) . . . . ?
S1 C11 N1 C14 7.1(3) . . . . ?
C15 C14 N1 C13 92.6(3) . . . . ?
C15 C14 N1 C11 -89.2(3) . . . . ?
C12 C11 S1 Ti1 34.4(2) . . . . ?
N1 C11 S1 Ti1 -146.0(2) . . . . ?
C11 C12 S2 Ti1 -30.9(2) . . . . ?
S3 C12 S2 Ti1 148.90(17) . . . . ?
C11 C12 S3 C13 -0.3(2) . . . . ?
S2 C12 S3 C13 179.88(18) . . . . ?
N1 C13 S3 C12 2.97(19) . . . . ?
S4 C13 S3 C12 -178.32(17) . . . . ?
C5 C1 Ti1 C2 115.9(2) . . . . ?
C5 C1 Ti1 C8 -171.71(17) . . . . ?
C2 C1 Ti1 C8 72.37(19) . . . . ?
C2 C1 Ti1 C5 -115.9(2) . . . . ?
C5 C1 Ti1 C6 -122.26(18) . . . . ?
C2 C1 Ti1 C6 121.81(19) . . . . ?
C5 C1 Ti1 C3 78.82(18) . . . . ?
C2 C1 Ti1 C3 -37.11(17) . . . . ?
C5 C1 Ti1 C7 -157.55(18) . . . . ?
C2 C1 Ti1 C7 86.52(18) . . . . ?
C5 C1 Ti1 C4 38.06(17) . . . . ?
C2 C1 Ti1 C4 -77.86(19) . . . . ?
C5 C1 Ti1 C9 -142.42(18) . . . . ?
C2 C1 Ti1 C9 101.6(2) . . . . ?
C5 C1 Ti1 C10 -110.88(18) . . . . ?
C2 C1 Ti1 C10 133.19(18) . . . . ?
C5 C1 Ti1 S2 -22.32(18) . . . . ?
C2 C1 Ti1 S2 -138.25(16) . . . . ?
C5 C1 Ti1 S1 85.07(18) . . . . ?
C2 C1 Ti1 S1 -30.9(2) . . . . ?
C3 C2 Ti1 C1 -115.7(3) . . . . ?
C3 C2 Ti1 C8 129.30(18) . . . . ?
C1 C2 Ti1 C8 -115.01(18) . . . . ?
C3 C2 Ti1 C5 -78.58(19) . . . . ?
C1 C2 Ti1 C5 37.12(16) . . . . ?
C3 C2 Ti1 C6 -173.12(18) . . . . ?
C1 C2 Ti1 C6 -57.43(18) . . . . ?
C1 C2 Ti1 C3 115.7(3) . . . . ?
C3 C2 Ti1 C7 158.7(2) . . . . ?
C1 C2 Ti1 C7 -85.65(18) . . . . ?
C3 C2 Ti1 C4 -36.96(17) . . . . ?
C1 C2 Ti1 C4 78.74(18) . . . . ?
C3 C2 Ti1 C9 134.11(18) . . . . ?
C1 C2 Ti1 C9 -110.20(19) . . . . ?
C3 C2 Ti1 C10 179.09(17) . . . . ?
C1 C2 Ti1 C10 -65.2(2) . . . . ?
C3 C2 Ti1 S2 -54.7(2) . . . . ?
C1 C2 Ti1 S2 61.0(2) . . . . ?
C3 C2 Ti1 S1 42.23(18) . . . . ?
C1 C2 Ti1 S1 157.93(15) . . . . ?
C9 C8 Ti1 C1 140.10(18) . . . . ?
C7 C8 Ti1 C1 25.1(2) . . . . ?
C9 C8 Ti1 C2 173.41(18) . . . . ?
C7 C8 Ti1 C2 58.43(19) . . . . ?
C9 C8 Ti1 C5 132.3(2) . . . . ?
C7 C8 Ti1 C5 17.3(3) . . . . ?
C9 C8 Ti1 C6 77.5(2) . . . . ?
C7 C8 Ti1 C6 -37.48(19) . . . . ?
C9 C8 Ti1 C3 -157.42(17) . . . . ?
C7 C8 Ti1 C3 87.6(2) . . . . ?
C9 C8 Ti1 C7 115.0(3) . . . . ?
C9 C8 Ti1 C4 -163.05(19) . . . . ?
C7 C8 Ti1 C4 82.0(3) . . . . ?
C7 C8 Ti1 C9 -115.0(3) . . . . ?
C9 C8 Ti1 C10 36.45(18) . . . . ?
C7 C8 Ti1 C10 -78.5(2) . . . . ?
C9 C8 Ti1 S2 -3.0(2) . . . . ?
C7 C8 Ti1 S2 -118.00(17) . . . . ?
C9 C8 Ti1 S1 -84.11(17) . . . . ?
C7 C8 Ti1 S1 160.90(18) . . . . ?
C4 C5 Ti1 C1 114.7(3) . . . . ?
C1 C5 Ti1 C2 -37.50(17) . . . . ?
C4 C5 Ti1 C2 77.24(19) . . . . ?
C1 C5 Ti1 C8 13.1(3) . . . . ?
C4 C5 Ti1 C8 127.8(2) . . . . ?
C1 C5 Ti1 C6 57.00(18) . . . . ?
C4 C5 Ti1 C6 171.74(19) . . . . ?
C1 C5 Ti1 C3 -78.45(18) . . . . ?
C4 C5 Ti1 C3 36.29(17) . . . . ?
C1 C5 Ti1 C7 23.34(19) . . . . ?
C4 C5 Ti1 C7 138.08(18) . . . . ?
C1 C5 Ti1 C4 -114.7(3) . . . . ?
C1 C5 Ti1 C9 77.9(3) . . . . ?
C4 C5 Ti1 C9 -167.4(2) . . . . ?
C1 C5 Ti1 C10 85.65(19) . . . . ?
C4 C5 Ti1 C10 -159.60(18) . . . . ?
C1 C5 Ti1 S2 159.23(17) . . . . ?
C4 C5 Ti1 S2 -86.03(17) . . . . ?
C1 C5 Ti1 S1 -122.18(15) . . . . ?
C4 C5 Ti1 S1 -7.4(2) . . . . ?
C10 C6 Ti1 C1 160.9(2) . . . . ?
C7 C6 Ti1 C1 -84.1(2) . . . . ?
C10 C6 Ti1 C2 -169.61(19) . . . . ?
C7 C6 Ti1 C2 -54.6(2) . . . . ?
C10 C6 Ti1 C8 -77.9(2) . . . . ?
C7 C6 Ti1 C8 37.13(19) . . . . ?
C10 C6 Ti1 C5 131.88(19) . . . . ?
C7 C6 Ti1 C5 -113.1(2) . . . . ?
C10 C6 Ti1 C3 -174.86(18) . . . . ?
C7 C6 Ti1 C3 -59.8(2) . . . . ?
C10 C6 Ti1 C7 -115.0(3) . . . . ?
C10 C6 Ti1 C4 138.3(2) . . . . ?
C7 C6 Ti1 C4 -106.7(2) . . . . ?
C10 C6 Ti1 C9 -36.80(18) . . . . ?
C7 C6 Ti1 C9 78.2(2) . . . . ?
C7 C6 Ti1 C10 115.0(3) . . . . ?
C10 C6 Ti1 S2 49.71(19) . . . . ?
C7 C6 Ti1 S2 164.74(18) . . . . ?
C10 C6 Ti1 S1 -49.2(2) . . . . ?
C7 C6 Ti1 S1 65.9(2) . . . . ?
C4 C3 Ti1 C1 -78.29(17) . . . . ?
C2 C3 Ti1 C1 37.70(17) . . . . ?
C4 C3 Ti1 C2 -116.0(2) . . . . ?
C4 C3 Ti1 C8 -175.00(16) . . . . ?
C2 C3 Ti1 C8 -59.0(2) . . . . ?
C4 C3 Ti1 C5 -37.06(16) . . . . ?
C2 C3 Ti1 C5 78.92(19) . . . . ?
C4 C3 Ti1 C6 -106.77(19) . . . . ?
C2 C3 Ti1 C6 9.2(2) . . . . ?
C4 C3 Ti1 C7 -138.24(17) . . . . ?
C2 C3 Ti1 C7 -22.3(2) . . . . ?
C2 C3 Ti1 C4 116.0(2) . . . . ?
C4 C3 Ti1 C9 162.26(18) . . . . ?
C2 C3 Ti1 C9 -81.8(2) . . . . ?
C4 C3 Ti1 C10 -118.8(5) . . . . ?
C2 C3 Ti1 C10 -2.8(5) . . . . ?
C4 C3 Ti1 S2 26.21(17) . . . . ?
C2 C3 Ti1 S2 142.19(16) . . . . ?
C4 C3 Ti1 S1 106.30(16) . . . . ?
C2 C3 Ti1 S1 -137.72(18) . . . . ?
C8 C7 Ti1 C1 -155.7(2) . . . . ?
C6 C7 Ti1 C1 88.6(2) . . . . ?
C8 C7 Ti1 C2 -119.9(2) . . . . ?
C6 C7 Ti1 C2 124.4(2) . . . . ?
C6 C7 Ti1 C8 -115.7(3) . . . . ?
C8 C7 Ti1 C5 -169.05(18) . . . . ?
C6 C7 Ti1 C5 75.3(2) . . . . ?
C8 C7 Ti1 C6 115.7(3) . . . . ?
C8 C7 Ti1 C3 -107.26(19) . . . . ?
C6 C7 Ti1 C3 137.06(19) . . . . ?
C8 C7 Ti1 C4 -137.79(19) . . . . ?
C6 C7 Ti1 C4 106.5(2) . . . . ?
C8 C7 Ti1 C9 37.59(18) . . . . ?
C6 C7 Ti1 C9 -78.1(2) . . . . ?
C8 C7 Ti1 C10 78.2(2) . . . . ?
C6 C7 Ti1 C10 -37.44(19) . . . . ?
C8 C7 Ti1 S2 93.95(19) . . . . ?
C6 C7 Ti1 S2 -21.7(3) . . . . ?
C8 C7 Ti1 S1 -21.7(2) . . . . ?
C6 C7 Ti1 S1 -137.39(18) . . . . ?
C3 C4 Ti1 C1 79.14(18) . . . . ?
C5 C4 Ti1 C1 -37.79(17) . . . . ?
C3 C4 Ti1 C2 37.27(16) . . . . ?
C5 C4 Ti1 C2 -79.66(18) . . . . ?
C3 C4 Ti1 C8 9.0(3) . . . . ?
C5 C4 Ti1 C8 -107.9(2) . . . . ?
C3 C4 Ti1 C5 116.9(2) . . . . ?
C3 C4 Ti1 C6 105.8(2) . . . . ?
C5 C4 Ti1 C6 -11.1(2) . . . . ?
C5 C4 Ti1 C3 -116.9(2) . . . . ?
C3 C4 Ti1 C7 58.2(2) . . . . ?
C5 C4 Ti1 C7 -58.7(2) . . . . ?
C3 C4 Ti1 C9 -98.8(7) . . . . ?
C5 C4 Ti1 C9 144.3(6) . . . . ?
C3 C4 Ti1 C10 154.7(2) . . . . ?
C5 C4 Ti1 C10 37.8(3) . . . . ?
C3 C4 Ti1 S2 -155.25(16) . . . . ?
C5 C4 Ti1 S2 87.82(17) . . . . ?
C3 C4 Ti1 S1 -69.33(16) . . . . ?
C5 C4 Ti1 S1 173.74(17) . . . . ?
C8 C9 Ti1 C1 -55.4(2) . . . . ?
C10 C9 Ti1 C1 61.2(2) . . . . ?
C8 C9 Ti1 C2 -8.5(2) . . . . ?
C10 C9 Ti1 C2 108.1(2) . . . . ?
C10 C9 Ti1 C8 116.6(3) . . . . ?
C8 C9 Ti1 C5 -104.3(3) . . . . ?
C10 C9 Ti1 C5 12.3(3) . . . . ?
C8 C9 Ti1 C6 -79.35(19) . . . . ?
C10 C9 Ti1 C6 37.26(18) . . . . ?
C8 C9 Ti1 C3 38.2(3) . . . . ?
C10 C9 Ti1 C3 154.8(2) . . . . ?
C8 C9 Ti1 C7 -37.65(17) . . . . ?
C10 C9 Ti1 C7 79.0(2) . . . . ?
C8 C9 Ti1 C4 122.2(6) . . . . ?
C10 C9 Ti1 C4 -121.2(6) . . . . ?
C8 C9 Ti1 C10 -116.6(3) . . . . ?
C8 C9 Ti1 S2 177.64(17) . . . . ?
C10 C9 Ti1 S2 -65.76(18) . . . . ?
C8 C9 Ti1 S1 92.54(18) . . . . ?
C10 C9 Ti1 S1 -150.85(18) . . . . ?
C6 C10 Ti1 C1 -20.2(2) . . . . ?
C9 C10 Ti1 C1 -136.10(18) . . . . ?
C6 C10 Ti1 C2 13.8(3) . . . . ?
C9 C10 Ti1 C2 -102.1(2) . . . . ?
C6 C10 Ti1 C8 79.0(2) . . . . ?
C9 C10 Ti1 C8 -36.90(18) . . . . ?
C6 C10 Ti1 C5 -57.6(2) . . . . ?
C9 C10 Ti1 C5 -173.58(17) . . . . ?
C9 C10 Ti1 C6 -115.9(3) . . . . ?
C6 C10 Ti1 C3 15.9(6) . . . . ?
C9 C10 Ti1 C3 -100.0(5) . . . . ?
C6 C10 Ti1 C7 37.86(18) . . . . ?
C9 C10 Ti1 C7 -78.1(2) . . . . ?
C6 C10 Ti1 C4 -81.3(3) . . . . ?
C9 C10 Ti1 C4 162.7(2) . . . . ?
C6 C10 Ti1 C9 115.9(3) . . . . ?
C6 C10 Ti1 S2 -131.20(19) . . . . ?
C9 C10 Ti1 S2 112.85(18) . . . . ?
C6 C10 Ti1 S1 147.55(17) . . . . ?
C9 C10 Ti1 S1 31.61(19) . . . . ?
C12 S2 Ti1 C1 173.82(12) . . . . ?
C12 S2 Ti1 C2 140.84(13) . . . . ?
C12 S2 Ti1 C8 -44.23(13) . . . . ?
C12 S2 Ti1 C5 161.19(11) . . . . ?
C12 S2 Ti1 C6 -102.61(12) . . . . ?
C12 S2 Ti1 C3 111.21(12) . . . . ?
C12 S2 Ti1 C7 -90.14(15) . . . . ?
C12 S2 Ti1 C4 125.80(12) . . . . ?
C12 S2 Ti1 C9 -45.93(12) . . . . ?
C12 S2 Ti1 C10 -76.86(12) . . . . ?
C12 S2 Ti1 S1 36.96(9) . . . . ?
C11 S1 Ti1 C1 -156.12(14) . . . . ?
C11 S1 Ti1 C2 -173.67(12) . . . . ?
C11 S1 Ti1 C8 91.30(12) . . . . ?
C11 S1 Ti1 C5 -113.82(13) . . . . ?
C11 S1 Ti1 C6 67.41(16) . . . . ?
C11 S1 Ti1 C3 -150.70(12) . . . . ?
C11 S1 Ti1 C7 103.35(13) . . . . ?
C11 S1 Ti1 C4 -118.07(12) . . . . ?
C11 S1 Ti1 C9 57.05(12) . . . . ?
C11 S1 Ti1 C10 39.98(12) . . . . ?
C11 S1 Ti1 S2 -37.94(9) . . . . ?


#----------------------------------------------------------------------------#
# END OF CIF FILE FOR DA35                                                   #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# 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_compound6a
_database_code_depnum_ccdc_archive 'CCDC 1405549'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2014-02-28T17:11:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H5 N1 O1 S4'
_chemical_formula_sum            'C6 H5 N O S4'
_chemical_formula_weight         235.35
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   10.4066(3)
_cell_length_b                   7.3334(2)
_cell_length_c                   12.2408(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.422(2)
_cell_angle_gamma                90
_cell_volume                     904.73(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4005
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      27.46
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.861


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_number            7682
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             2068
_reflns_number_gt                1918
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0237P)²+0.5402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2068
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.08
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.056

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'


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
C1 C 0.62610(19) -0.4061(3) 0.15865(16) 0.0305(4) Uani 1 1 d . . .
H1A H 0.7138 -0.3764 0.1476 0.046 Uiso 1 1 calc R . .
H1B H 0.5781 -0.4834 0.0965 0.046 Uiso 1 1 calc R . .
H1C H 0.6365 -0.4712 0.2302 0.046 Uiso 1 1 calc R . .
C2 C 0.54858(16) -0.2314(2) 0.16125(14) 0.0222(4) Uani 1 1 d . . .
H2A H 0.5329 -0.1696 0.0872 0.027 Uiso 1 1 calc R . .
H2B H 0.4613 -0.261 0.1754 0.027 Uiso 1 1 calc R . .
N3 N 0.62216(13) -0.10857(19) 0.25033(11) 0.0175(3) Uani 1 1 d . . .
C4 C 0.61482(15) -0.1190(2) 0.35962(13) 0.0179(3) Uani 1 1 d . . .
C5 C 0.78403(15) 0.1010(2) 0.32727(13) 0.0178(3) Uani 1 1 d . . .
C6 C 0.71576(15) 0.0156(2) 0.23319(13) 0.0181(3) Uani 1 1 d . . .
C7 C 0.87194(16) 0.2363(2) 0.16513(14) 0.0206(3) Uani 1 1 d . . .
O1 O 0.92937(12) 0.32208(19) 0.10872(10) 0.0290(3) Uani 1 1 d . . .
S2 S 0.51101(4) -0.24953(6) 0.40931(4) 0.02360(11) Uani 1 1 d . . .
S3 S 0.73056(4) 0.02807(6) 0.44363(3) 0.01930(11) Uani 1 1 d . . .
S4 S 0.90273(4) 0.25975(6) 0.31427(3) 0.02143(11) Uani 1 1 d . . .
S5 S 0.74836(4) 0.06936(6) 0.10464(3) 0.02126(11) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.518(3) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 N3 1.473(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
N3 C4 1.361(2) . ?
N3 C6 1.387(2) . ?
C4 S2 1.6676(16) . ?
C4 S3 1.7476(16) . ?
C5 C6 1.347(2) . ?
C5 S4 1.7334(16) . ?
C5 S3 1.7375(16) . ?
C6 S5 1.7356(16) . ?
C7 O1 1.198(2) . ?
C7 S4 1.7815(17) . ?
C7 S5 1.7963(17) . ?


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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 C1 110.52(14) . . ?
N3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 N3 C6 113.51(13) . . ?
C4 N3 C2 123.17(13) . . ?
C6 N3 C2 123.00(13) . . ?
N3 C4 S2 126.21(12) . . ?
N3 C4 S3 110.16(11) . . ?
S2 C4 S3 123.63(9) . . ?
C6 C5 S4 118.01(12) . . ?
C6 C5 S3 110.45(12) . . ?
S4 C5 S3 131.53(10) . . ?
C5 C6 N3 114.61(14) . . ?
C5 C6 S5 119.27(13) . . ?
N3 C6 S5 126.11(12) . . ?
O1 C7 S4 123.48(14) . . ?
O1 C7 S5 121.94(13) . . ?
S4 C7 S5 114.57(9) . . ?
C5 S3 C4 91.26(8) . . ?
C5 S4 C7 94.52(8) . . ?
C6 S5 C7 93.58(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
C1 C2 N3 C4 -85.74(19) . . . . ?
C1 C2 N3 C6 87.31(19) . . . . ?
C6 N3 C4 S2 178.34(12) . . . . ?
C2 N3 C4 S2 -8.0(2) . . . . ?
C6 N3 C4 S3 -1.09(17) . . . . ?
C2 N3 C4 S3 172.56(12) . . . . ?
S4 C5 C6 N3 -179.67(11) . . . . ?
S3 C5 C6 N3 -0.61(19) . . . . ?
S4 C5 C6 S5 -0.6(2) . . . . ?
S3 C5 C6 S5 178.50(9) . . . . ?
C4 N3 C6 C5 1.1(2) . . . . ?
C2 N3 C6 C5 -172.52(15) . . . . ?
C4 N3 C6 S5 -177.91(12) . . . . ?
C2 N3 C6 S5 8.4(2) . . . . ?
C6 C5 S3 C4 -0.01(13) . . . . ?
S4 C5 S3 C4 178.87(13) . . . . ?
N3 C4 S3 C5 0.62(12) . . . . ?
S2 C4 S3 C5 -178.82(12) . . . . ?
C6 C5 S4 C7 1.50(15) . . . . ?
S3 C5 S4 C7 -177.32(13) . . . . ?
O1 C7 S4 C5 179.03(16) . . . . ?
S5 C7 S4 C5 -1.91(11) . . . . ?
C5 C6 S5 C7 -0.71(15) . . . . ?
N3 C6 S5 C7 178.29(15) . . . . ?
O1 C7 S5 C6 -179.25(16) . . . . ?
S4 C7 S5 C6 1.68(11) . . . . ?


#----------------------------------------------------------------------------#
# END OF CIF FILE FOR DA41                                                   #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# 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_compound6c
_database_code_depnum_ccdc_archive 'CCDC 1405550'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2015-04-15T17:45:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H5 N O S4'
_chemical_formula_sum            'C10 H5 N O S4'
_chemical_formula_weight         283.39
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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                   9.5493(5)
_cell_length_b                   8.4524(5)
_cell_length_c                   14.3009(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.898(3)
_cell_angle_gamma                90
_cell_volume                     1115.49(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3855
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.29
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.787


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_number            8223
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             2535
_reflns_number_gt                2243
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0340P)²+0.3697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2535
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.075
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.086

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'


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
O1 O 0.35133(15) 0.13433(19) 0.45286(10) 0.0296(4) Uani 1 1 d . . .
C2 C 0.3966(2) 0.2366(2) 0.51089(13) 0.0204(4) Uani 1 1 d . . .
C3 C 0.42447(18) 0.4833(2) 0.61993(12) 0.0160(4) Uani 1 1 d . . .
C4 C 0.55818(19) 0.4189(2) 0.63914(13) 0.0166(4) Uani 1 1 d . . .
C5 C 0.54293(18) 0.6615(2) 0.73654(13) 0.0160(4) Uani 1 1 d . . .
N6 N 0.41540(15) 0.62080(19) 0.67189(10) 0.0154(3) Uani 1 1 d . . .
C7 C 0.28342(18) 0.7125(2) 0.65665(12) 0.0158(4) Uani 1 1 d . . .
C8 C 0.16107(19) 0.6422(3) 0.67351(13) 0.0205(4) Uani 1 1 d . . .
H8 H 0.1644 0.5371 0.6975 0.025 Uiso 1 1 calc R . .
C9 C 0.0328(2) 0.7295(3) 0.65439(14) 0.0232(4) Uani 1 1 d . . .
H9 H -0.0525 0.6836 0.6651 0.028 Uiso 1 1 calc R . .
C10 C 0.0297(2) 0.8826(3) 0.61997(13) 0.0228(4) Uani 1 1 d . . .
H10 H -0.0583 0.9409 0.6064 0.027 Uiso 1 1 calc R . .
C11 C 0.1542(2) 0.9522(3) 0.60495(13) 0.0217(4) Uani 1 1 d . . .
H11 H 0.1514 1.0582 0.5824 0.026 Uiso 1 1 calc R . .
C12 C 0.2824(2) 0.8669(2) 0.62282(12) 0.0187(4) Uani 1 1 d . . .
H12 H 0.3678 0.9129 0.6122 0.022 Uiso 1 1 calc R . .
S1 S 0.28293(5) 0.39295(6) 0.53625(3) 0.02017(13) Uani 1 1 d . . .
S2 S 0.58165(5) 0.24638(6) 0.57920(3) 0.01920(13) Uani 1 1 d . . .
S3 S 0.67957(4) 0.52878(6) 0.72631(3) 0.01682(12) Uani 1 1 d . . .
S4 S 0.56945(5) 0.80675(6) 0.81726(3) 0.02062(13) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C2 1.199(2) . ?
C2 S2 1.7881(19) . ?
C2 S1 1.805(2) . ?
C3 C4 1.350(2) . ?
C3 N6 1.394(2) . ?
C3 S1 1.7351(18) . ?
C4 S2 1.735(2) . ?
C4 S3 1.7370(19) . ?
C5 N6 1.370(2) . ?
C5 S4 1.659(2) . ?
C5 S3 1.7553(19) . ?
N6 C7 1.447(2) . ?
C7 C8 1.386(2) . ?
C7 C12 1.391(3) . ?
C8 C9 1.395(3) . ?
C8 H8 0.95 . ?
C9 C10 1.382(3) . ?
C9 H9 0.95 . ?
C10 C11 1.392(3) . ?
C10 H10 0.95 . ?
C11 C12 1.387(3) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?


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 C2 S2 122.74(16) . . ?
O1 C2 S1 122.59(15) . . ?
S2 C2 S1 114.67(11) . . ?
C4 C3 N6 114.39(16) . . ?
C4 C3 S1 119.43(15) . . ?
N6 C3 S1 126.18(13) . . ?
C3 C4 S2 118.29(15) . . ?
C3 C4 S3 110.63(14) . . ?
S2 C4 S3 131.06(11) . . ?
N6 C5 S4 127.26(14) . . ?
N6 C5 S3 109.51(14) . . ?
S4 C5 S3 123.17(10) . . ?
C5 N6 C3 113.75(15) . . ?
C5 N6 C7 123.75(16) . . ?
C3 N6 C7 122.49(14) . . ?
C8 C7 C12 122.14(17) . . ?
C8 C7 N6 118.99(17) . . ?
C12 C7 N6 118.84(15) . . ?
C7 C8 C9 118.42(19) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 120.18(18) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.60(18) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
C11 C12 C7 118.59(17) . . ?
C11 C12 H12 120.7 . . ?
C7 C12 H12 120.7 . . ?
C3 S1 C2 93.37(9) . . ?
C4 S2 C2 94.22(9) . . ?
C4 S3 C5 91.63(9) . . ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 C3 C4 S2 179.48(12) . . . . ?
S1 C3 C4 S2 -0.5(2) . . . . ?
N6 C3 C4 S3 1.0(2) . . . . ?
S1 C3 C4 S3 -178.99(10) . . . . ?
S4 C5 N6 C3 -173.95(14) . . . . ?
S3 C5 N6 C3 3.34(19) . . . . ?
S4 C5 N6 C7 7.3(3) . . . . ?
S3 C5 N6 C7 -175.43(13) . . . . ?
C4 C3 N6 C5 -2.9(2) . . . . ?
S1 C3 N6 C5 177.07(13) . . . . ?
C4 C3 N6 C7 175.90(16) . . . . ?
S1 C3 N6 C7 -4.1(2) . . . . ?
C5 N6 C7 C8 -120.0(2) . . . . ?
C3 N6 C7 C8 61.3(2) . . . . ?
C5 N6 C7 C12 61.8(2) . . . . ?
C3 N6 C7 C12 -116.82(19) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
N6 C7 C8 C9 -177.16(16) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
N6 C7 C12 C11 177.65(16) . . . . ?
C4 C3 S1 C2 -0.40(17) . . . . ?
N6 C3 S1 C2 179.64(16) . . . . ?
O1 C2 S1 C3 -178.95(18) . . . . ?
S2 C2 S1 C3 1.11(12) . . . . ?
C3 C4 S2 C2 1.08(17) . . . . ?
S3 C4 S2 C2 179.23(14) . . . . ?
O1 C2 S2 C4 178.75(18) . . . . ?
S1 C2 S2 C4 -1.31(12) . . . . ?
C3 C4 S3 C5 0.79(15) . . . . ?
S2 C4 S3 C5 -177.46(14) . . . . ?
N6 C5 S3 C4 -2.34(14) . . . . ?
S4 C5 S3 C4 175.08(13) . . . . ?


#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR Y377                                                 #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# 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_compound6d
_database_code_depnum_ccdc_archive 'CCDC 1405551'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2015-02-18T09:20:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H5 N O2 S3'
_chemical_formula_sum            'C6 H5 N O2 S3'
_chemical_formula_weight         219.29
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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                   8.5086(16)
_cell_length_b                   9.106(3)
_cell_length_c                   11.589(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.442(8)
_cell_angle_gamma                90
_cell_volume                     841.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    246
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.16
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.839


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_number            5513
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             1912
_reflns_number_gt                1679
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0363P)²+0.2630P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1912
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.033
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.074

# End of res file

#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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 0.89399(6) 0.51947(5) 0.64100(5) 0.02148(15) Uani 1 1 d . . .
S2 S 0.79653(6) 0.72302(5) 0.42274(5) 0.01938(15) Uani 1 1 d . . .
S3 S 0.52065(6) 0.48845(5) 0.28856(4) 0.01808(14) Uani 1 1 d . . .
C1 C 0.7362(2) 0.4656(2) 0.50663(18) 0.0169(4) Uani 1 1 d . . .
N2 N 0.63775(19) 0.34028(17) 0.49188(14) 0.0167(3) Uani 1 1 d . . .
C3 C 0.6622(3) 0.2207(2) 0.58203(19) 0.0199(4) Uani 1 1 d . . .
H3A H 0.5516 0.1794 0.5748 0.024 Uiso 1 1 calc R . .
H3B H 0.7136 0.2614 0.6661 0.024 Uiso 1 1 calc R . .
C4 C 0.7722(3) 0.0992(2) 0.5645(2) 0.0284(5) Uani 1 1 d . . .
H4A H 0.7254 0.062 0.4799 0.043 Uiso 1 1 calc R . .
H4B H 0.7774 0.0193 0.6224 0.043 Uiso 1 1 calc R . .
H4C H 0.8854 0.1372 0.5797 0.043 Uiso 1 1 calc R . .
C5 C 0.5135(2) 0.3314(2) 0.37922(17) 0.0169(4) Uani 1 1 d . . .
O6 O 0.41109(18) 0.23178(15) 0.34358(13) 0.0227(3) Uani 1 1 d . . .
C7 C 0.6923(2) 0.5562(2) 0.40807(17) 0.0164(4) Uani 1 1 d . . .
C8 C 0.9260(2) 0.6932(2) 0.57916(19) 0.0220(4) Uani 1 1 d . . .
O9 O 1.03028(19) 0.77930(17) 0.63750(15) 0.0335(4) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.734(2) . ?
S1 C8 1.796(2) . ?
S2 C7 1.737(2) . ?
S2 C8 1.783(2) . ?
S3 C7 1.7375(19) . ?
S3 C5 1.788(2) . ?
C1 C7 1.352(3) . ?
C1 N2 1.390(2) . ?
N2 C5 1.366(2) . ?
N2 C3 1.472(2) . ?
C3 C4 1.508(3) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 O6 1.225(2) . ?
C8 O9 1.200(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
C1 S1 C8 93.94(9) . . ?
C7 S2 C8 94.56(9) . . ?
C7 S3 C5 90.43(9) . . ?
C7 C1 N2 114.87(17) . . ?
C7 C1 S1 118.98(15) . . ?
N2 C1 S1 125.94(15) . . ?
C5 N2 C1 113.45(16) . . ?
C5 N2 C3 120.35(16) . . ?
C1 N2 C3 126.14(16) . . ?
N2 C3 C4 112.80(16) . . ?
N2 C3 H3A 109 . . ?
C4 C3 H3A 109 . . ?
N2 C3 H3B 109 . . ?
C4 C3 H3B 109 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O6 C5 N2 126.00(18) . . ?
O6 C5 S3 124.08(15) . . ?
N2 C5 S3 109.92(14) . . ?
C1 C7 S2 118.05(15) . . ?
C1 C7 S3 111.33(15) . . ?
S2 C7 S3 130.32(12) . . ?
O9 C8 S2 123.10(17) . . ?
O9 C8 S1 122.40(16) . . ?
S2 C8 S1 114.44(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
C8 S1 C1 C7 1.13(18) . . . . ?
C8 S1 C1 N2 -173.29(17) . . . . ?
C7 C1 N2 C5 0.1(2) . . . . ?
S1 C1 N2 C5 174.72(14) . . . . ?
C7 C1 N2 C3 177.22(17) . . . . ?
S1 C1 N2 C3 -8.2(3) . . . . ?
C5 N2 C3 C4 85.8(2) . . . . ?
C1 N2 C3 C4 -91.1(2) . . . . ?
C1 N2 C5 O6 179.59(18) . . . . ?
C3 N2 C5 O6 2.3(3) . . . . ?
C1 N2 C5 S3 -0.3(2) . . . . ?
C3 N2 C5 S3 -177.63(13) . . . . ?
C7 S3 C5 O6 -179.56(18) . . . . ?
C7 S3 C5 N2 0.36(14) . . . . ?
N2 C1 C7 S2 174.56(13) . . . . ?
S1 C1 C7 S2 -0.5(2) . . . . ?
N2 C1 C7 S3 0.2(2) . . . . ?
S1 C1 C7 S3 -174.83(10) . . . . ?
C8 S2 C7 C1 -0.49(18) . . . . ?
C8 S2 C7 S3 172.63(15) . . . . ?
C5 S3 C7 C1 -0.31(16) . . . . ?
C5 S3 C7 S2 -173.79(15) . . . . ?
C7 S2 C8 O9 178.7(2) . . . . ?
C7 S2 C8 S1 1.22(13) . . . . ?
C1 S1 C8 O9 -178.88(19) . . . . ?
C1 S1 C8 S2 -1.39(13) . . . . ?


#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR Y360                                                 #
#----------------------------------------------------------------------------#
