# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

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

data_KI32
_database_code_depnum_ccdc_archive 'CCDC 1558710'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                              CHEMICAL_INFORMATION                          #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H6 N2 S6'
_chemical_formula_sum            'C8 H6 N2 S6'
_chemical_formula_weight         322.51
_chemical_compound_source        'synthesis as described'

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


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

_cell_length_a                   4.0461(3)
_cell_length_b                   9.9861(7)
_cell_length_c                   14.8584(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.697(3)
_cell_angle_gamma                90
_cell_volume                     598.33(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3826
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       stick
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             328
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.967

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0398
_diffrn_reflns_av_uneti/neti     0.0358
_diffrn_reflns_number            5524
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.425
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             1359
_reflns_number_gt                1270
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'SAINT (Bruker, 2014); XPREP (Sheldrick, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014); XPREP (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CRYSCALc (T. Roisnel, local program, 2015)'

#----------------------------------------------------------------------------#
#                             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     
'w=1/[σ²(Fo²)+5.8684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1359
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.348
_refine_ls_restrained_S_all      1.348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.152

# End of res file

#
# .hkl SHELXL file: KI32.hkl
#
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                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 0.0000 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'

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 0.5475(13) -0.4597(5) 0.4659(3) 0.0104(10) Uani 1 1 d . . .
C2 C 0.5118(14) -0.3147(5) 0.4636(3) 0.0119(10) Uani 1 1 d . . .
C3 C 0.7611(13) -0.3522(5) 0.3298(4) 0.0121(10) Uani 1 1 d . . .
C4 C 0.6300(17) -0.1175(6) 0.3703(4) 0.0218(13) Uani 1 1 d . . .
H4A H 0.7292 -0.0993 0.3136 0.033 Uiso 1 1 calc R U .
H4B H 0.7574 -0.0714 0.4200 0.033 Uiso 1 1 calc R U .
H4C H 0.4005 -0.0853 0.3659 0.033 Uiso 1 1 calc R U .
N1 N 0.6345(12) -0.2618(4) 0.3875(3) 0.0139(9) Uani 1 1 d . . .
S1 S 0.7286(3) -0.51643(13) 0.37010(9) 0.0130(3) Uani 1 1 d . . .
S2 S 0.3476(4) -0.22383(14) 0.54074(10) 0.0193(4) Uani 1 1 d . . .
S3 S 0.9275(4) -0.31976(15) 0.23530(9) 0.0196(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
C1 C1 1.375(10) 3_646 ?
C1 C2 1.455(7) . ?
C1 S1 1.747(5) . ?
C2 N1 1.377(7) . ?
C2 S2 1.644(5) . ?
C3 N1 1.373(7) . ?
C3 S3 1.639(5) . ?
C3 S1 1.755(5) . ?
C4 N1 1.463(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C2 124.5(6) 3_646 . ?
C1 C1 S1 124.9(5) 3_646 . ?
C2 C1 S1 110.6(4) . . ?
N1 C2 C1 111.0(5) . . ?
N1 C2 S2 123.6(4) . . ?
C1 C2 S2 125.3(4) . . ?
N1 C3 S3 127.3(4) . . ?
N1 C3 S1 111.1(4) . . ?
S3 C3 S1 121.6(3) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 C2 116.0(4) . . ?
C3 N1 C4 122.6(5) . . ?
C2 N1 C4 121.4(5) . . ?
C1 S1 C3 91.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 N1 178.9(6) 3_646 . . . ?
S1 C1 C2 N1 -0.9(6) . . . . ?
C1 C1 C2 S2 -1.1(10) 3_646 . . . ?
S1 C1 C2 S2 179.1(3) . . . . ?
S3 C3 N1 C2 -179.2(4) . . . . ?
S1 C3 N1 C2 0.3(6) . . . . ?
S3 C3 N1 C4 0.6(8) . . . . ?
S1 C3 N1 C4 -180.0(4) . . . . ?
C1 C2 N1 C3 0.4(7) . . . . ?
S2 C2 N1 C3 -179.6(4) . . . . ?
C1 C2 N1 C4 -179.4(5) . . . . ?
S2 C2 N1 C4 0.7(8) . . . . ?
C1 C1 S1 C3 -178.9(6) 3_646 . . . ?
C2 C1 S1 C3 0.9(4) . . . . ?
N1 C3 S1 C1 -0.7(4) . . . . ?
S3 C3 S1 C1 178.8(4) . . . . ?
####################################################################### 
# 
# 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_KI30
_database_code_depnum_ccdc_archive 'CCDC 1558724'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C14 H18 N2 O2 S4'
_chemical_formula_moiety         'C14 H18 N2 O2 S4'
_chemical_formula_weight         374.55
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   32.967(9)
_cell_length_b                   8.079(4)
_cell_length_c                   6.986(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1860.9(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      14.98
_cell_measurement_theta_max      17.13
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784.00
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  0.940

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

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω
_diffrn_reflns_number            3593
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -0.221

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2700
_reflns_number_gt                1214
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1778
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2700
_refine_ls_number_parameters     100
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0753P)²+0.3346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.48198(3) 1.10684(10) 0.27787(12) 0.0599(3) Uani 1.0 8 d . . .
S2 S 0.40595(3) 1.10580(12) 0.50061(14) 0.0818(4) Uani 1.0 8 d . . .
O1 O 0.43827(7) 0.8407(3) -0.1240(3) 0.0660(7) Uani 1.0 8 d . . .
N1 N 0.41722(8) 0.9584(3) 0.1600(4) 0.0533(7) Uani 1.0 8 d . . .
C1 C 0.48410(9) 1.0048(4) 0.0597(4) 0.0491(7) Uani 1.0 8 d . . .
C2 C 0.43124(10) 1.0512(4) 0.3104(5) 0.0586(9) Uani 1.0 8 d . . .
C3 C 0.44489(10) 0.9248(4) 0.0159(5) 0.0535(8) Uani 1.0 8 d . . .
C4 C 0.37627(10) 0.8887(4) 0.1497(6) 0.0656(9) Uani 1.0 8 d . . .
C5 C 0.34857(12) 0.9948(6) 0.0229(7) 0.0973(14) Uani 1.0 8 d . . .
C6 C 0.30778(15) 0.9239(7) 0.0063(8) 0.133(2) Uani 1.0 8 d . . .
C7 C 0.2811(2) 1.0367(13) -0.1205(13) 0.239(5) Uani 1.0 8 d . . .
H4A H 0.3649 0.8822 0.2775 0.0787 Uiso 1.0 8 calc R . .
H4B H 0.3776 0.7774 0.0982 0.0787 Uiso 1.0 8 calc R . .
H5A H 0.3466 1.1052 0.0766 0.1168 Uiso 1.0 8 calc R . .
H5B H 0.3605 1.0042 -0.1037 0.1168 Uiso 1.0 8 calc R . .
H6A H 0.2957 0.9135 0.1324 0.1600 Uiso 1.0 8 calc R . .
H6B H 0.3094 0.8143 -0.0500 0.1600 Uiso 1.0 8 calc R . .
H7A H 0.2932 1.0472 -0.2448 0.2872 Uiso 1.0 8 calc R . .
H7B H 0.2789 1.1441 -0.0624 0.2872 Uiso 1.0 8 calc R . .
H7C H 0.2546 0.9890 -0.1328 0.2872 Uiso 1.0 8 calc R . .



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

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.734(3) yes . .
S1 C2 1.747(4) yes . .
S2 C2 1.630(4) yes . .
O1 C3 1.210(4) yes . .
N1 C2 1.371(4) yes . .
N1 C3 1.385(4) yes . .
N1 C4 1.464(5) yes . .
C1 C1 1.342(4) yes . 5_675
C1 C3 1.477(5) yes . .
C4 C5 1.534(6) yes . .
C5 C6 1.466(7) yes . .
C6 C7 1.546(11) yes . .
C4 H4A 0.970 no . .
C4 H4B 0.970 no . .
C5 H5A 0.970 no . .
C5 H5B 0.970 no . .
C6 H6A 0.970 no . .
C6 H6B 0.970 no . .
C7 H7A 0.960 no . .
C7 H7B 0.960 no . .
C7 H7C 0.960 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C2 91.74(15) yes . . .
C2 N1 C3 116.2(3) yes . . .
C2 N1 C4 124.0(3) yes . . .
C3 N1 C4 119.7(3) yes . . .
S1 C1 C1 127.2(3) yes . . 5_675
S1 C1 C3 110.8(2) yes . . .
C1 C1 C3 122.0(3) yes 5_675 . .
S1 C2 S2 121.73(19) yes . . .
S1 C2 N1 111.4(3) yes . . .
S2 C2 N1 126.9(3) yes . . .
O1 C3 N1 125.3(3) yes . . .
O1 C3 C1 124.8(3) yes . . .
N1 C3 C1 109.9(3) yes . . .
N1 C4 C5 111.3(3) yes . . .
C4 C5 C6 111.9(4) yes . . .
C5 C6 C7 109.7(5) yes . . .
N1 C4 H4A 109.380 no . . .
N1 C4 H4B 109.373 no . . .
C5 C4 H4A 109.363 no . . .
C5 C4 H4B 109.377 no . . .
H4A C4 H4B 108.003 no . . .
C4 C5 H5A 109.226 no . . .
C4 C5 H5B 109.215 no . . .
C6 C5 H5A 109.232 no . . .
C6 C5 H5B 109.229 no . . .
H5A C5 H5B 107.913 no . . .
C5 C6 H6A 109.731 no . . .
C5 C6 H6B 109.736 no . . .
C7 C6 H6A 109.723 no . . .
C7 C6 H6B 109.727 no . . .
H6A C6 H6B 108.208 no . . .
C6 C7 H7A 109.470 no . . .
C6 C7 H7B 109.475 no . . .
C6 C7 H7C 109.472 no . . .
H7A C7 H7B 109.474 no . . .
H7A C7 H7C 109.471 no . . .
H7B C7 H7C 109.466 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C2 S2 179.6(2) no . . . .
C1 S1 C2 N1 0.2(2) no . . . .
C2 S1 C1 C1 178.8(3) no . . . 5_675
C2 S1 C1 C3 -1.06(18) no . . . .
C2 N1 C3 O1 177.5(3) no . . . .
C2 N1 C3 C1 -1.6(4) no . . . .
C3 N1 C2 S1 0.8(4) no . . . .
C3 N1 C2 S2 -178.6(3) no . . . .
C2 N1 C4 C5 100.1(4) no . . . .
C4 N1 C2 S1 177.8(3) no . . . .
C4 N1 C2 S2 -1.5(5) no . . . .
C3 N1 C4 C5 -83.0(3) no . . . .
C4 N1 C3 O1 0.3(5) no . . . .
C4 N1 C3 C1 -178.7(3) no . . . .
S1 C1 C1 S1 -180(2) no . . 5_675 5_675
S1 C1 C1 C3 0.2(4) no . . 5_675 5_675
S1 C1 C3 O1 -177.4(3) no . . . .
S1 C1 C3 N1 1.7(3) no . . . .
C1 C1 C3 O1 2.7(5) no 5_675 . . .
C1 C1 C3 N1 -178.2(3) no 5_675 . . .
C3 C1 C1 S1 -0.2(4) no . . 5_675 5_675
C3 C1 C1 C3 180(3) no . . 5_675 5_675
N1 C4 C5 C6 178.2(3) no . . . .
C4 C5 C6 C7 179.2(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O1 2.872(3) no . 5_675
S1 C3 3.176(4) no . 5_675
S2 C4 3.169(4) no . .
O1 C1 2.883(4) no . 5_675
O1 C2 3.486(4) no . .
O1 C4 2.826(5) no . .
O1 C5 3.369(5) no . .
C2 C5 3.416(6) no . .
C3 C5 3.226(6) no . .
S1 C1 3.588(3) no . 7_655
S2 O1 3.550(3) no . 1_556
O1 S2 3.550(3) no . 1_554
O1 N1 2.932(4) no . 3_564
O1 C2 3.207(4) no . 3_564
O1 C3 3.313(4) no . 3_564
O1 C4 3.180(4) no . 3_564
N1 O1 2.932(4) no . 3_565
C1 S1 3.588(3) no . 7_645
C2 O1 3.207(4) no . 3_565
C3 O1 3.313(4) no . 3_565
C4 O1 3.180(4) no . 3_565
S2 H4A 2.7432 no . .
S2 H5A 3.5494 no . .
O1 H4B 2.5819 no . .
O1 H5B 2.8885 no . .
N1 H5A 2.6762 no . .
N1 H5B 2.6515 no . .
C2 H4A 2.5884 no . .
C2 H4B 3.1958 no . .
C2 H5A 3.2615 no . .
C3 H4A 3.2270 no . .
C3 H4B 2.5815 no . .
C3 H5A 3.5775 no . .
C3 H5B 2.9757 no . .
C4 H6A 2.6658 no . .
C4 H6B 2.6769 no . .
C5 H7A 2.6472 no . .
C5 H7B 2.6611 no . .
C5 H7C 3.2852 no . .
C6 H4A 2.6922 no . .
C6 H4B 2.6679 no . .
C7 H5A 2.6211 no . .
C7 H5B 2.6328 no . .
H4A H5A 2.3612 no . .
H4A H5B 2.8427 no . .
H4A H6A 2.5084 no . .
H4A H6B 2.9802 no . .
H4B H5A 2.8429 no . .
H4B H5B 2.3804 no . .
H4B H6A 2.9260 no . .
H4B H6B 2.4942 no . .
H5A H6A 2.3163 no . .
H5A H6B 2.7947 no . .
H5A H7A 2.8921 no . .
H5A H7B 2.4544 no . .
H5A H7C 3.4982 no . .
H5B H6A 2.7948 no . .
H5B H6B 2.3078 no . .
H5B H7A 2.4516 no . .
H5B H7B 2.9304 no . .
H5B H7C 3.5000 no . .
H6A H7A 2.8488 no . .
H6A H7B 2.3722 no . .
H6A H7C 2.3760 no . .
H6B H7A 2.3825 no . .
H6B H7B 2.8487 no . .
H6B H7C 2.3657 no . .
S2 H4B 3.3044 no . 3_565
S2 H5A 3.0919 no . 3_575
S2 H5B 3.2506 no . 1_556
S2 H5B 3.5650 no . 3_575
O1 H4A 3.0935 no . 3_564
O1 H4B 2.9448 no . 3_564
C4 H4A 3.4197 no . 3_564
C4 H4B 3.4092 no . 3_565
C4 H6B 3.4572 no . 3_565
C5 H4A 3.5364 no . 3_564
C6 H4A 3.4952 no . 3_564
C6 H7C 3.3282 no . 4_575
C7 H6A 3.0913 no . 4_574
H4A O1 3.0935 no . 3_565
H4A C4 3.4197 no . 3_565
H4A C5 3.5364 no . 3_565
H4A C6 3.4952 no . 3_565
H4A H4B 2.6192 no . 3_565
H4A H5B 3.2336 no . 3_565
H4A H6B 2.7055 no . 3_565
H4B S2 3.3044 no . 3_564
H4B O1 2.9448 no . 3_565
H4B C4 3.4092 no . 3_564
H4B H4A 2.6192 no . 3_564
H4B H4B 3.5211 no . 3_564
H4B H4B 3.5211 no . 3_565
H4B H5B 3.1357 no . 3_565
H4B H6B 3.4130 no . 3_565
H5A S2 3.0919 no . 3_574
H5A H7A 3.5422 no . 3_575
H5B S2 3.2506 no . 1_554
H5B S2 3.5650 no . 3_574
H5B H4A 3.2336 no . 3_564
H5B H4B 3.1357 no . 3_564
H6A C7 3.0913 no . 4_575
H6A H6B 2.9185 no . 3_565
H6A H7A 3.0713 no . 4_575
H6A H7B 3.5565 no . 2_545
H6A H7B 3.2894 no . 4_575
H6A H7C 2.4614 no . 4_575
H6B C4 3.4572 no . 3_564
H6B H4A 2.7055 no . 3_564
H6B H4B 3.4130 no . 3_564
H6B H6A 2.9185 no . 3_564
H6B H7B 3.2220 no . 2_545
H6B H7C 3.4190 no . 2_545
H7A H5A 3.5422 no . 3_574
H7A H6A 3.0713 no . 4_574
H7A H7B 3.3717 no . 3_574
H7A H7C 3.1484 no . 4_574
H7B H6A 3.5565 no . 2_555
H7B H6A 3.2894 no . 4_574
H7B H6B 3.2220 no . 2_555
H7B H7A 3.3717 no . 3_575
H7B H7C 3.0373 no . 2_555
H7B H7C 3.3740 no . 4_575
H7C C6 3.3282 no . 4_574
H7C H6A 2.4614 no . 4_574
H7C H6B 3.4190 no . 2_555
H7C H7A 3.1484 no . 4_575
H7C H7B 3.0373 no . 2_545
H7C H7B 3.3740 no . 4_574
H7C H7C 3.5106 no . 4_574
H7C H7C 3.5106 no . 4_575
####################################################################### 
# 
# 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_KI28
_database_code_depnum_ccdc_archive 'CCDC 1558718'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C8 H6 N2 O2 S4'
_chemical_formula_moiety         'C8 H6 N2 O2 S4'
_chemical_formula_weight         290.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.7328(5)
_cell_length_b                   5.6266(10)
_cell_length_c                   10.8786(16)
_cell_angle_alpha                81.629(13)
_cell_angle_beta                 80.329(12)
_cell_angle_gamma                84.727(13)
_cell_volume                     281.86(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      15.13
_cell_measurement_theta_max      16.99
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             148.00
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.984

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

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            2001
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_full        29.98
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -0.136

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1642
_reflns_number_gt                1086
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0948
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1642
_refine_ls_number_parameters     73
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0357P)²+0.0756P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87862(12) 0.35240(11) 0.38007(5) 0.04099(17) Uani 1.0 2 d . . .
S2 S 1.20557(14) 0.53366(13) 0.13174(6) 0.0541(3) Uani 1.0 2 d . . .
O1 O 0.3426(4) 0.9039(4) 0.38050(17) 0.0567(5) Uani 1.0 2 d . . .
N1 N 0.7462(5) 0.7622(4) 0.25393(18) 0.0396(5) Uani 1.0 2 d . . .
C1 C 0.5845(5) 0.5268(4) 0.44427(19) 0.0345(5) Uani 1.0 2 d . . .
C2 C 0.5358(5) 0.7524(5) 0.3604(2) 0.0397(5) Uani 1.0 2 d . . .
C3 C 0.9421(5) 0.5689(5) 0.2475(2) 0.0383(5) Uani 1.0 2 d . . .
C4 C 0.7442(7) 0.9647(5) 0.1533(3) 0.0544(7) Uani 1.0 2 d . . .
H4A H 0.7284 0.9066 0.0762 0.0652 Uiso 1.0 2 calc R . .
H4B H 0.9193 1.0441 0.1431 0.0652 Uiso 1.0 2 calc R . .
H4C H 0.5836 1.0763 0.1746 0.0652 Uiso 1.0 2 calc R . .



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


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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.735(2) yes . .
S1 C3 1.751(3) yes . .
S2 C3 1.637(3) yes . .
O1 C2 1.206(3) yes . .
N1 C2 1.393(3) yes . .
N1 C3 1.364(3) yes . .
N1 C4 1.461(3) yes . .
C1 C1 1.347(3) yes . 2_666
C1 C2 1.476(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C3 91.28(10) yes . . .
C2 N1 C3 116.25(19) yes . . .
C2 N1 C4 120.8(2) yes . . .
C3 N1 C4 122.86(19) yes . . .
S1 C1 C1 126.69(17) yes . . 2_666
S1 C1 C2 111.33(15) yes . . .
C1 C1 C2 121.99(19) yes 2_666 . .
O1 C2 N1 125.3(2) yes . . .
O1 C2 C1 125.2(2) yes . . .
N1 C2 C1 109.41(19) yes . . .
S1 C3 S2 122.40(14) yes . . .
S1 C3 N1 111.71(15) yes . . .
S2 C3 N1 125.88(17) yes . . .
####################################################################### 
# 
# 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_KI27
_database_code_depnum_ccdc_archive 'CCDC 1558711'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                              CHEMICAL_INFORMATION                          #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C3 H3.50 N0.50 S1.50'
_chemical_formula_sum            'C3 H3.50 N0.50 S1.50'
_chemical_formula_weight         94.65
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      Triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
x,y,z
-x,-y,-z

_cell_length_a                   4.3845(2)
_cell_length_b                   7.1311(4)
_cell_length_c                   12.7965(6)
_cell_angle_alpha                90.248(2)
_cell_angle_beta                 97.646(2)
_cell_angle_gamma                98.184(2)
_cell_volume                     392.39(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6223
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.933

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0202
_diffrn_reflns_av_uneti/neti     0.0168
_diffrn_reflns_number            7560
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.21
_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             1789
_reflns_number_gt                1703
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'SAINT (Bruker, 2014); XPREP (Sheldrick, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014); XPREP (Sheldrick, 2014)'
_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  'CRYSCALc (T. Roisnel, local program, 2015)'

#----------------------------------------------------------------------------#
#                             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)+(0.0177P)²+0.1847P] 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         1789
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0476
_refine_ls_wR_factor_gt          0.0468
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.047

# End of res file

#
# .hkl SHELXL file: KI27.hkl
#
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                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 0.0000 0.0000 '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'
N N 0.0061 0.0033 '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 0.5426(2) 0.46725(15) 0.45429(8) 0.0117(2) Uani 1 1 d . . .
C2 C 0.7400(2) 0.58181(15) 0.38813(8) 0.0126(2) Uani 1 1 d . . .
C3 C 0.6417(3) 0.29159(16) 0.29471(9) 0.0143(2) Uani 1 1 d . . .
C4 C 0.9701(3) 0.55870(16) 0.22101(9) 0.0158(2) Uani 1 1 d . . .
H4A H 1.0717 0.4600 0.1904 0.019 Uiso 1 1 calc R . .
H4B H 1.1349 0.6597 0.2532 0.019 Uiso 1 1 calc R . .
C5 C 0.7603(3) 0.64170(16) 0.13397(9) 0.0170(2) Uani 1 1 d . . .
H5A H 0.6119 0.5379 0.0963 0.020 Uiso 1 1 calc R . .
H5B H 0.6388 0.7281 0.1660 0.020 Uiso 1 1 calc R . .
C6 C 0.9462(3) 0.75020(19) 0.05531(10) 0.0243(3) Uani 1 1 d . . .
H6A H 1.0846 0.8577 0.0916 0.037 Uiso 1 1 calc R . .
H6B H 0.8033 0.7969 -0.0008 0.037 Uiso 1 1 calc R . .
H6C H 1.0702 0.6658 0.0246 0.037 Uiso 1 1 calc R . .
S1 S 0.43269(6) 0.23729(4) 0.40121(2) 0.01338(8) Uani 1 1 d . . .
S2 S 0.65016(8) 0.13611(4) 0.20114(2) 0.02209(9) Uani 1 1 d . . .
S3 S 0.88377(7) 0.80638(4) 0.41002(2) 0.01792(8) Uani 1 1 d . . .
N1 N 0.7897(2) 0.47528(13) 0.30278(7) 0.01309(19) 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 C1 1.374(2) 2_666 ?
C1 C2 1.4606(15) . ?
C1 S1 1.7495(11) . ?
C2 N1 1.3860(14) . ?
C2 S3 1.6438(11) . ?
C3 N1 1.3735(14) . ?
C3 S2 1.6359(11) . ?
C3 S1 1.7559(12) . ?
C4 N1 1.4717(14) . ?
C4 C5 1.5248(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5237(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C2 124.11(12) 2_666 . ?
C1 C1 S1 125.19(11) 2_666 . ?
C2 C1 S1 110.70(8) . . ?
N1 C2 C1 110.61(9) . . ?
N1 C2 S3 124.02(8) . . ?
C1 C2 S3 125.37(8) . . ?
N1 C3 S2 126.81(9) . . ?
N1 C3 S1 111.08(8) . . ?
S2 C3 S1 122.11(7) . . ?
N1 C4 C5 110.77(9) . . ?
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 . . ?
C6 C5 C4 111.88(10) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 S1 C3 91.43(5) . . ?
C3 N1 C2 116.15(9) . . ?
C3 N1 C4 121.86(9) . . ?
C2 N1 C4 121.81(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
C1 C1 C2 N1 178.72(12) 2_666 . . . ?
S1 C1 C2 N1 -1.08(11) . . . . ?
C1 C1 C2 S3 -1.65(19) 2_666 . . . ?
S1 C1 C2 S3 178.55(6) . . . . ?
N1 C4 C5 C6 172.99(10) . . . . ?
C1 C1 S1 C3 -179.83(13) 2_666 . . . ?
C2 C1 S1 C3 -0.04(8) . . . . ?
N1 C3 S1 C1 1.16(8) . . . . ?
S2 C3 S1 C1 -179.13(7) . . . . ?
S2 C3 N1 C2 178.20(8) . . . . ?
S1 C3 N1 C2 -2.10(12) . . . . ?
S2 C3 N1 C4 2.95(15) . . . . ?
S1 C3 N1 C4 -177.36(8) . . . . ?
C1 C2 N1 C3 2.06(13) . . . . ?
S3 C2 N1 C3 -177.57(8) . . . . ?
C1 C2 N1 C4 177.32(9) . . . . ?
S3 C2 N1 C4 -2.31(14) . . . . ?
C5 C4 N1 C3 86.66(12) . . . . ?
C5 C4 N1 C2 -88.33(12) . . . . ?
####################################################################### 
# 
# 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_KI29
_database_code_depnum_ccdc_archive 'CCDC 1558720'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C10 H10 N2 O2 S4'
_chemical_formula_moiety         'C10 H10 N2 O2 S4'
_chemical_formula_weight         318.44
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   23.646(9)
_cell_length_b                   7.940(5)
_cell_length_c                   7.200(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1351.9(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      15.06
_cell_measurement_theta_max      17.50
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.055
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.00
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.962

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

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω
_diffrn_reflns_number            2606
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_full        29.97
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        0.280

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1960
_reflns_number_gt                938
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1049
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1960
_refine_ls_number_parameters     82
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0325P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.48048(3) 0.39881(9) 0.22197(10) 0.0430(2) Uani 1.0 8 d . . .
S2 S 0.37771(3) 0.39363(10) -0.01060(11) 0.0620(3) Uani 1.0 8 d . . .
O1 O 0.41031(8) 0.6505(3) 0.6107(3) 0.0524(6) Uani 1.0 8 d . . .
N1 N 0.38685(9) 0.5390(3) 0.3252(3) 0.0362(5) Uani 1.0 8 d . . .
C1 C 0.47870(10) 0.4950(3) 0.4380(4) 0.0342(6) Uani 1.0 8 d . . .
C2 C 0.42260(11) 0.5713(3) 0.4726(4) 0.0381(7) Uani 1.0 8 d . . .
C3 C 0.40935(11) 0.4494(3) 0.1802(4) 0.0402(7) Uani 1.0 8 d . . .
C4 C 0.32852(11) 0.6044(4) 0.3281(4) 0.0463(7) Uani 1.0 8 d . . .
C5 C 0.28910(12) 0.4897(5) 0.4299(6) 0.0882(12) Uani 1.0 8 d . . .
H4A H 0.3153 0.6183 0.2016 0.0556 Uiso 1.0 8 calc R . .
H4B H 0.3283 0.7142 0.3872 0.0556 Uiso 1.0 8 calc R . .
H5A H 0.3011 0.4797 0.5569 0.1058 Uiso 1.0 8 calc R . .
H5B H 0.2894 0.3806 0.3725 0.1058 Uiso 1.0 8 calc R . .
H5C H 0.2515 0.5351 0.4258 0.1058 Uiso 1.0 8 calc R . .



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

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.734(3) yes . .
S1 C3 1.755(3) yes . .
S2 C3 1.626(3) yes . .
O1 C2 1.211(4) yes . .
N1 C2 1.381(4) yes . .
N1 C3 1.371(4) yes . .
N1 C4 1.474(4) yes . .
C1 C1 1.348(4) yes . 5_666
C1 C2 1.480(4) yes . .
C4 C5 1.495(5) yes . .
C4 H4A 0.970 no . .
C4 H4B 0.970 no . .
C5 H5A 0.960 no . .
C5 H5B 0.960 no . .
C5 H5C 0.960 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C3 91.68(13) yes . . .
C2 N1 C3 116.4(3) yes . . .
C2 N1 C4 119.8(2) yes . . .
C3 N1 C4 123.8(3) yes . . .
S1 C1 C1 127.0(2) yes . . 5_666
S1 C1 C2 110.70(18) yes . . .
C1 C1 C2 122.3(3) yes 5_666 . .
O1 C2 N1 125.5(3) yes . . .
O1 C2 C1 124.5(3) yes . . .
N1 C2 C1 110.1(3) yes . . .
S1 C3 S2 121.54(16) yes . . .
S1 C3 N1 111.13(19) yes . . .
S2 C3 N1 127.3(2) yes . . .
N1 C4 C5 112.1(3) yes . . .
N1 C4 H4A 109.202 no . . .
N1 C4 H4B 109.195 no . . .
C5 C4 H4A 109.194 no . . .
C5 C4 H4B 109.199 no . . .
H4A C4 H4B 107.897 no . . .
C4 C5 H5A 109.474 no . . .
C4 C5 H5B 109.463 no . . .
C4 C5 H5C 109.472 no . . .
H5A C5 H5B 109.467 no . . .
H5A C5 H5C 109.473 no . . .
H5B C5 H5C 109.477 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C3 S2 -179.15(18) no . . . .
C1 S1 C3 N1 1.34(17) no . . . .
C3 S1 C1 C1 178.9(2) no . . . 5_666
C3 S1 C1 C2 -1.95(16) no . . . .
C2 N1 C3 S1 -0.3(3) no . . . .
C2 N1 C3 S2 -179.8(2) no . . . .
C3 N1 C2 O1 178.8(3) no . . . .
C3 N1 C2 C1 -1.2(3) no . . . .
C2 N1 C4 C5 -85.1(3) no . . . .
C4 N1 C2 O1 0.5(4) no . . . .
C4 N1 C2 C1 -179.44(19) no . . . .
C3 N1 C4 C5 96.7(3) no . . . .
C4 N1 C3 S1 177.89(19) no . . . .
C4 N1 C3 S2 -1.6(4) no . . . .
S1 C1 C1 S1 180(17) no . . 5_666 5_666
S1 C1 C1 C2 -0.9(4) no . . 5_666 5_666
S1 C1 C2 O1 -177.84(19) no . . . .
S1 C1 C2 N1 2.1(3) no . . . .
C1 C1 C2 O1 1.4(4) no 5_666 . . .
C1 C1 C2 N1 -178.7(2) no 5_666 . . .
C2 C1 C1 S1 0.9(4) no . . 5_666 5_666
C2 C1 C1 C2 180(2) no . . 5_666 5_666

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O1 2.876(3) no . 5_666
S1 C2 3.185(3) no . 5_666
S2 C4 3.178(3) no . .
O1 C1 2.889(4) no . 5_666
O1 C3 3.486(4) no . .
O1 C4 2.831(4) no . .
O1 C5 3.397(4) no . .
C2 C5 3.237(4) no . .
C3 C5 3.379(5) no . .
S1 C1 3.541(3) no . 7_645
S2 O1 3.492(3) no . 1_554
S2 C3 3.597(3) no . 3_554
O1 S2 3.492(3) no . 1_556
O1 N1 2.962(3) no . 3_565
O1 C2 3.428(4) no . 3_565
O1 C3 3.216(4) no . 3_565
O1 C4 3.159(4) no . 3_565
N1 O1 2.962(3) no . 3_564
C1 S1 3.541(3) no . 7_655
C2 O1 3.428(4) no . 3_564
C3 S2 3.597(3) no . 3_555
C3 O1 3.216(4) no . 3_564
C4 O1 3.159(4) no . 3_564
S2 H4A 2.7741 no . .
S2 H5B 3.4605 no . .
O1 H4B 2.5709 no . .
O1 H5A 2.9436 no . .
N1 H5A 2.6680 no . .
N1 H5B 2.6464 no . .
N1 H5C 3.2815 no . .
C2 H4A 3.2232 no . .
C2 H4B 2.5772 no . .
C2 H5A 3.0261 no . .
C2 H5B 3.5678 no . .
C3 H4A 2.6018 no . .
C3 H4B 3.2119 no . .
C3 H5B 3.2022 no . .
H4A H5A 2.8053 no . .
H4A H5B 2.3347 no . .
H4A H5C 2.3062 no . .
H4B H5A 2.3183 no . .
H4B H5B 2.8056 no . .
H4B H5C 2.3226 no . .
S2 H4B 3.4067 no . 3_564
S2 H5A 3.5080 no . 3_554
S2 H5B 3.1314 no . 3_554
S2 H5C 3.1409 no . 4_564
O1 H4A 2.9743 no . 3_565
O1 H4B 2.9802 no . 3_565
C4 H4A 3.4893 no . 3_565
C4 H4B 3.4865 no . 3_564
C4 H5B 3.5624 no . 2_555
C5 H4A 3.2638 no . 4_565
C5 H4B 3.5468 no . 2_545
C5 H5A 3.4381 no . 4_564
H4A O1 2.9743 no . 3_564
H4A C4 3.4893 no . 3_564
H4A C5 3.2638 no . 4_564
H4A H4B 2.6433 no . 3_564
H4A H5A 3.3747 no . 3_564
H4A H5A 3.0428 no . 4_564
H4A H5B 3.4615 no . 2_555
H4A H5B 3.4274 no . 4_564
H4A H5C 2.8141 no . 4_564
H4B S2 3.4067 no . 3_565
H4B O1 2.9802 no . 3_564
H4B C4 3.4865 no . 3_565
H4B C5 3.5468 no . 2_555
H4B H4A 2.6433 no . 3_565
H4B H5A 3.4611 no . 3_564
H4B H5B 3.0826 no . 2_555
H4B H5C 3.1821 no . 2_555
H5A S2 3.5080 no . 3_555
H5A C5 3.4381 no . 4_565
H5A H4A 3.3747 no . 3_565
H5A H4A 3.0428 no . 4_565
H5A H4B 3.4611 no . 3_565
H5A H5B 3.3129 no . 4_565
H5A H5C 2.9352 no . 4_565
H5B S2 3.1314 no . 3_555
H5B C4 3.5624 no . 2_545
H5B H4A 3.4615 no . 2_545
H5B H4A 3.4274 no . 4_565
H5B H4B 3.0826 no . 2_545
H5B H5A 3.3129 no . 4_564
H5B H5C 2.9343 no . 2_545
H5B H5C 3.4247 no . 4_564
H5C S2 3.1409 no . 4_565
H5C H4A 2.8141 no . 4_565
H5C H4B 3.1821 no . 2_545
H5C H5A 2.9352 no . 4_564
H5C H5B 2.9343 no . 2_555
H5C H5B 3.4247 no . 4_565
####################################################################### 
# 
# 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_O-N-Pr5
_database_code_depnum_ccdc_archive 'CCDC 1558721'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C12 H14 N2 O2 S4'
_chemical_formula_moiety         'C12 H14 N2 O2 S4'
_chemical_formula_weight         346.49
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.8023(2)
_cell_length_b                   8.15218(10)
_cell_length_c                   7.03233(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.4020
_cell_angle_gamma                90.0000
_cell_volume                     772.806(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8317
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      68.28
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.025
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360.00
_exptl_absorpt_coefficient_mu    5.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  0.868

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

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8634
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1414
_reflns_number_gt                1306
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1284
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1414
_refine_ls_number_parameters     91
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0806P)²+0.1079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45712(4) 0.39124(6) 0.20598(8) 0.0470(3) Uani 1.0 4 d . . .
S2 S 0.27133(5) 0.38945(8) -0.09623(9) 0.0664(3) Uani 1.0 4 d . . .
O1 O 0.34870(10) 0.6607(2) 0.5528(2) 0.0547(4) Uani 1.0 4 d . . .
N1 N 0.29857(10) 0.54267(18) 0.2503(3) 0.0404(4) Uani 1.0 4 d . . .
C1 C 0.46140(12) 0.4946(2) 0.4234(3) 0.0395(4) Uani 1.0 4 d . . .
C2 C 0.33263(14) 0.4471(3) 0.1176(3) 0.0445(5) Uani 1.0 4 d . . .
C3 C 0.36569(13) 0.5766(3) 0.4220(3) 0.0400(5) Uani 1.0 4 d . . .
C4 C 0.19906(14) 0.6152(3) 0.2144(4) 0.0457(5) Uani 1.0 4 d . . .
C5 C 0.12731(14) 0.5172(3) 0.3029(4) 0.0573(6) Uani 1.0 4 d . . .
C6 C 0.02669(17) 0.6001(4) 0.2670(4) 0.0677(7) Uani 1.0 4 d . . .
H4A H 0.1735 0.6235 0.0751 0.0549 Uiso 1.0 4 calc R . .
H4B H 0.2037 0.7254 0.2678 0.0549 Uiso 1.0 4 calc R . .
H5A H 0.1531 0.5062 0.4419 0.0688 Uiso 1.0 4 calc R . .
H5B H 0.1203 0.4081 0.2465 0.0688 Uiso 1.0 4 calc R . .
H6A H 0.0336 0.7082 0.3225 0.0813 Uiso 1.0 4 calc R . .
H6B H -0.0175 0.5369 0.3262 0.0813 Uiso 1.0 4 calc R . .
H6C H 0.0003 0.6078 0.1294 0.0813 Uiso 1.0 4 calc R . .



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

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.7354(19) yes . .
S1 C2 1.7571(19) yes . .
S2 C2 1.6284(19) yes . .
O1 C3 1.210(3) yes . .
N1 C2 1.373(3) yes . .
N1 C3 1.383(3) yes . .
N1 C4 1.467(3) yes . .
C1 C1 1.346(3) yes . 3_666
C1 C3 1.479(3) yes . .
C4 C5 1.507(4) yes . .
C5 C6 1.516(3) yes . .
C4 H4A 0.970 no . .
C4 H4B 0.970 no . .
C5 H5A 0.970 no . .
C5 H5B 0.970 no . .
C6 H6A 0.960 no . .
C6 H6B 0.960 no . .
C6 H6C 0.960 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C2 91.80(9) yes . . .
C2 N1 C3 116.34(15) yes . . .
C2 N1 C4 123.81(15) yes . . .
C3 N1 C4 119.77(16) yes . . .
S1 C1 C1 127.49(15) yes . . 3_666
S1 C1 C3 110.63(12) yes . . .
C1 C1 C3 121.88(17) yes 3_666 . .
S1 C2 S2 121.76(13) yes . . .
S1 C2 N1 110.99(13) yes . . .
S2 C2 N1 127.25(14) yes . . .
O1 C3 N1 125.04(17) yes . . .
O1 C3 C1 124.75(16) yes . . .
N1 C3 C1 110.21(16) yes . . .
N1 C4 C5 112.93(16) yes . . .
C4 C5 C6 110.77(19) yes . . .
N1 C4 H4A 108.996 no . . .
N1 C4 H4B 108.999 no . . .
C5 C4 H4A 109.003 no . . .
C5 C4 H4B 108.999 no . . .
H4A C4 H4B 107.785 no . . .
C4 C5 H5A 109.486 no . . .
C4 C5 H5B 109.485 no . . .
C6 C5 H5A 109.488 no . . .
C6 C5 H5B 109.497 no . . .
H5A C5 H5B 108.068 no . . .
C5 C6 H6A 109.474 no . . .
C5 C6 H6B 109.470 no . . .
C5 C6 H6C 109.466 no . . .
H6A C6 H6B 109.474 no . . .
H6A C6 H6C 109.472 no . . .
H6B C6 H6C 109.471 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C2 S2 -179.57(14) no . . . .
C1 S1 C2 N1 0.98(14) no . . . .
C2 S1 C1 C1 178.97(16) no . . . 3_666
C2 S1 C1 C3 -1.78(12) no . . . .
C2 N1 C3 O1 178.71(17) no . . . .
C2 N1 C3 C1 -1.5(3) no . . . .
C3 N1 C2 S1 0.2(2) no . . . .
C3 N1 C2 S2 -179.25(15) no . . . .
C2 N1 C4 C5 98.6(2) no . . . .
C4 N1 C2 S1 176.83(14) no . . . .
C4 N1 C2 S2 -2.6(3) no . . . .
C3 N1 C4 C5 -84.87(19) no . . . .
C4 N1 C3 O1 1.9(3) no . . . .
C4 N1 C3 C1 -178.31(14) no . . . .
S1 C1 C1 S1 180.00(11) no . . 3_666 3_666
S1 C1 C1 C3 -0.8(3) no . . 3_666 3_666
S1 C1 C3 O1 -178.04(14) no . . . .
S1 C1 C3 N1 2.17(18) no . . . .
C1 C1 C3 O1 1.3(3) no 3_666 . . .
C1 C1 C3 N1 -178.53(16) no 3_666 . . .
C3 C1 C1 S1 0.8(3) no . . 3_666 3_666
C3 C1 C1 C3 180.00(18) no . . 3_666 3_666
N1 C4 C5 C6 178.25(15) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O1 2.8788(14) no . 3_666
S1 C3 3.1853(18) no . 3_666
S2 C4 3.177(3) no . .
O1 C1 2.883(3) no . 3_666
O1 C2 3.486(3) no . .
O1 C4 2.820(3) no . .
O1 C5 3.389(3) no . .
C2 C5 3.412(4) no . .
C3 C5 3.252(3) no . .
O1 N1 2.944(3) no . 4_565
O1 C2 3.244(3) no . 4_565
O1 C3 3.335(3) no . 4_565
O1 C4 3.147(3) no . 4_565
N1 O1 2.944(3) no . 4_564
C2 O1 3.244(3) no . 4_564
C3 O1 3.335(3) no . 4_564
C4 O1 3.147(3) no . 4_564
S2 H4A 2.7592 no . .
S2 H5B 3.5117 no . .
O1 H4B 2.5648 no . .
O1 H5A 2.9290 no . .
N1 H5A 2.6643 no . .
N1 H5B 2.6883 no . .
C2 H4A 2.5880 no . .
C2 H4B 3.1993 no . .
C2 H5B 3.2632 no . .
C3 H4A 3.2178 no . .
C3 H4B 2.5703 no . .
C3 H5A 3.0225 no . .
C4 H6A 2.6666 no . .
C4 H6B 3.3126 no . .
C4 H6C 2.6806 no . .
C6 H4A 2.6719 no . .
C6 H4B 2.6464 no . .
H4A H5A 2.8214 no . .
H4A H5B 2.3355 no . .
H4A H6A 2.9454 no . .
H4A H6B 3.5459 no . .
H4A H6C 2.5046 no . .
H4B H5A 2.3548 no . .
H4B H5B 2.8212 no . .
H4B H6A 2.4624 no . .
H4B H6B 3.5201 no . .
H4B H6C 2.9281 no . .
H5A H6A 2.3534 no . .
H5A H6B 2.3340 no . .
H5A H6C 2.8239 no . .
H5B H6A 2.8241 no . .
H5B H6B 2.3444 no . .
H5B H6C 2.3430 no . .
S2 H4B 3.3561 no . 4_564
S2 H5A 3.4413 no . 1_554
S2 H5B 3.2344 no . 4_554
S2 H6B 3.5796 no . 3_565
O1 H4A 3.0213 no . 4_565
O1 H4B 2.9079 no . 4_565
C4 H4A 3.3879 no . 4_565
C4 H4B 3.4126 no . 4_564
C4 H6A 3.4898 no . 4_564
C5 H4A 3.4821 no . 4_565
C5 H6A 3.3494 no . 2_545
C5 H6B 3.3152 no . 3_566
C5 H6C 3.3287 no . 3_565
C6 H4A 3.4629 no . 4_565
C6 H5B 3.2170 no . 2_555
C6 H6A 3.3278 no . 2_545
C6 H6A 3.5140 no . 4_564
C6 H6B 3.0988 no . 3_566
C6 H6C 3.2149 no . 3_565
C6 H6C 3.5631 no . 4_565
H4A O1 3.0213 no . 4_564
H4A C4 3.3879 no . 4_564
H4A C5 3.4821 no . 4_564
H4A C6 3.4629 no . 4_564
H4A H4B 2.5976 no . 4_564
H4A H5A 3.1550 no . 4_564
H4A H6A 2.7003 no . 4_564
H4A H6B 3.4203 no . 3_565
H4A H6C 3.1458 no . 3_565
H4B S2 3.3561 no . 4_565
H4B O1 2.9079 no . 4_564
H4B C4 3.4126 no . 4_565
H4B H4A 2.5976 no . 4_565
H4B H4B 3.5390 no . 4_564
H4B H4B 3.5390 no . 4_565
H4B H5A 3.1369 no . 4_564
H4B H6A 3.5282 no . 4_564
H4B H6B 3.5716 no . 2_555
H5A S2 3.4413 no . 1_556
H5A H4A 3.1550 no . 4_565
H5A H4B 3.1369 no . 4_565
H5A H6B 2.7556 no . 3_566
H5B S2 3.2344 no . 4_555
H5B C6 3.2170 no . 2_545
H5B H6A 2.6394 no . 2_545
H5B H6B 3.3351 no . 2_545
H5B H6C 3.1859 no . 2_545
H5B H6C 2.8078 no . 3_565
H6A C4 3.4898 no . 4_565
H6A C5 3.3494 no . 2_555
H6A C6 3.3278 no . 2_555
H6A C6 3.5140 no . 4_565
H6A H4A 2.7003 no . 4_565
H6A H4B 3.5282 no . 4_565
H6A H5B 2.6394 no . 2_555
H6A H6A 3.5817 no . 4_564
H6A H6A 3.5817 no . 4_565
H6A H6B 2.8678 no . 2_555
H6A H6B 3.2213 no . 3_566
H6A H6C 3.3192 no . 2_555
H6A H6C 2.7468 no . 4_565
H6B S2 3.5796 no . 3_565
H6B C5 3.3152 no . 3_566
H6B C6 3.0988 no . 3_566
H6B H4A 3.4203 no . 3_565
H6B H4B 3.5716 no . 2_545
H6B H5A 2.7556 no . 3_566
H6B H5B 3.3351 no . 2_555
H6B H6A 2.8678 no . 2_545
H6B H6A 3.2213 no . 3_566
H6B H6B 2.4619 no . 3_566
H6B H6C 3.5150 no . 2_545
H6B H6C 3.4702 no . 3_565
H6B H6C 3.5734 no . 4_565
H6C C5 3.3287 no . 3_565
H6C C6 3.2149 no . 3_565
H6C C6 3.5631 no . 4_564
H6C H4A 3.1458 no . 3_565
H6C H5B 3.1859 no . 2_555
H6C H5B 2.8078 no . 3_565
H6C H6A 3.3192 no . 2_545
H6C H6A 2.7468 no . 4_564
H6C H6B 3.5150 no . 2_555
H6C H6B 3.4702 no . 3_565
H6C H6B 3.5734 no . 4_564
H6C H6C 2.5292 no . 3_565
