# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_k10157
_database_code_depnum_ccdc_archive 'CCDC 1470545'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
4,5-dioxo-naphtho[1,2-d][1,2,3]dithiazol-2-ium
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N O2 S2, Cl4 Fe'
_chemical_formula_sum            'C10 H4 Cl4 Fe N O2 S2'
_chemical_formula_weight         431.91

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   10.3004(3)
_cell_length_b                   11.1497(5)
_cell_length_c                   13.8083(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.605(2)
_cell_angle_gamma                90.00
_cell_volume                     1484.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    4602
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.8

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_absorpt_coefficient_mu    2.012
# Absorption correction 

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(1)
_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  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9399
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         27.51
_reflns_number_total             3376
_reflns_number_gt                2592
_reflns_threshold_expression     I>2σ(I)


_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        Denzo-SMN
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'

_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)+(0.0461P)²+0.3665P] 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         3376
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
S2 S -0.01256(7) 0.15973(6) 0.04233(5) 0.02635(18) Uani 1 1 d . . .
S1 S 0.06720(7) 0.29341(6) 0.14468(5) 0.02372(17) Uani 1 1 d . . .
O2 O 0.3347(2) 0.38651(18) 0.30030(15) 0.0291(5) Uani 1 1 d . . .
O1 O 0.59222(19) 0.30207(19) 0.32252(16) 0.0339(5) Uani 1 1 d . . .
N1 N 0.1271(2) 0.0897(2) 0.05356(17) 0.0224(5) Uani 1 1 d . . .
C10 C 0.2284(3) 0.2407(2) 0.17331(19) 0.0195(5) Uani 1 1 d . . .
C9 C 0.3487(3) 0.3018(2) 0.2507(2) 0.0210(6) Uani 1 1 d . . .
C8 C 0.4928(3) 0.2493(3) 0.2644(2) 0.0241(6) Uani 1 1 d . . .
C7 C 0.4994(3) 0.1381(2) 0.2086(2) 0.0223(6) Uani 1 1 d . . .
C6 C 0.6288(3) 0.0846(3) 0.2277(2) 0.0284(7) Uani 1 1 d . . .
H6A H 0.7098 0.1221 0.2739 0.034 Uiso 1 1 calc R . .
C5 C 0.6405(3) -0.0215(3) 0.1806(2) 0.0318(7) Uani 1 1 d . . .
H5A H 0.7291 -0.0568 0.1941 0.038 Uiso 1 1 calc R . .
C4 C 0.5222(3) -0.0768(3) 0.1129(2) 0.0303(7) Uani 1 1 d . . .
H4A H 0.5303 -0.1503 0.0807 0.036 Uiso 1 1 calc R . .
C3 C 0.3926(3) -0.0254(3) 0.0920(2) 0.0253(6) Uani 1 1 d . . .
H3A H 0.3124 -0.0633 0.0453 0.030 Uiso 1 1 calc R . .
C2 C 0.3799(3) 0.0815(2) 0.1395(2) 0.0207(6) Uani 1 1 d . . .
C1 C 0.2437(3) 0.1361(2) 0.12110(19) 0.0196(5) Uani 1 1 d . . .
Fe1 Fe 0.18265(4) 0.06569(3) 0.44303(3) 0.02187(13) Uani 1 1 d . . .
Cl1 Cl 0.16451(8) -0.11940(7) 0.48852(6) 0.0349(2) Uani 1 1 d . . .
Cl2 Cl -0.00102(7) 0.11124(8) 0.31053(6) 0.0349(2) Uani 1 1 d . . .
Cl3 Cl 0.22555(7) 0.19521(7) 0.57110(5) 0.02871(18) Uani 1 1 d . . .
Cl4 Cl 0.36445(7) 0.07673(6) 0.39256(5) 0.02467(17) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2 0.0206(3) 0.0225(4) 0.0287(4) -0.0019(3) -0.0004(3) 0.0016(3)
S1 0.0210(3) 0.0202(4) 0.0274(4) -0.0010(3) 0.0053(3) 0.0016(3)
O2 0.0308(11) 0.0243(11) 0.0290(10) -0.0058(9) 0.0066(9) 0.0000(9)
O1 0.0234(10) 0.0334(12) 0.0395(12) -0.0067(10) 0.0045(10) -0.0071(9)
N1 0.0240(11) 0.0179(12) 0.0223(12) 0.0005(9) 0.0045(10) 0.0010(9)
C10 0.0216(13) 0.0185(13) 0.0185(12) 0.0024(11) 0.0070(11) -0.0018(11)
C9 0.0238(13) 0.0174(14) 0.0209(13) 0.0012(11) 0.0067(11) -0.0005(11)
C8 0.0218(13) 0.0255(15) 0.0244(14) 0.0027(12) 0.0072(12) -0.0018(12)
C7 0.0210(13) 0.0235(15) 0.0232(13) 0.0052(11) 0.0088(11) -0.0011(11)
C6 0.0233(14) 0.0333(17) 0.0282(15) 0.0048(13) 0.0087(13) 0.0005(12)
C5 0.0266(15) 0.0328(17) 0.0383(17) 0.0076(14) 0.0143(13) 0.0094(13)
C4 0.0341(16) 0.0250(15) 0.0352(16) -0.0003(13) 0.0164(14) 0.0050(13)
C3 0.0268(14) 0.0223(15) 0.0282(14) -0.0002(12) 0.0112(12) 0.0000(12)
C2 0.0220(13) 0.0190(14) 0.0214(13) 0.0038(11) 0.0077(11) 0.0001(11)
C1 0.0222(13) 0.0176(13) 0.0181(13) 0.0044(11) 0.0060(11) -0.0008(11)
Fe1 0.0232(2) 0.0202(2) 0.0221(2) -0.00086(15) 0.00778(17) -0.00293(16)
Cl1 0.0531(5) 0.0218(4) 0.0389(4) -0.0005(3) 0.0275(4) -0.0049(3)
Cl2 0.0227(3) 0.0501(5) 0.0285(4) 0.0023(3) 0.0047(3) -0.0019(3)
Cl3 0.0298(4) 0.0277(4) 0.0283(4) -0.0070(3) 0.0098(3) -0.0025(3)
Cl4 0.0242(3) 0.0243(4) 0.0266(3) 0.0011(3) 0.0104(3) -0.0013(3)

_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
S2 N1 1.596(2) . ?
S2 S1 2.0190(9) . ?
S1 C10 1.672(3) . ?
O2 C9 1.205(3) . ?
O1 C8 1.209(3) . ?
N1 C1 1.338(3) . ?
C10 C1 1.409(4) . ?
C10 C9 1.486(4) . ?
C9 C8 1.544(4) . ?
C8 C7 1.474(4) . ?
C7 C6 1.398(4) . ?
C7 C2 1.413(4) . ?
C6 C5 1.376(4) . ?
C5 C4 1.392(4) . ?
C4 C3 1.387(4) . ?
C3 C2 1.388(4) . ?
C2 C1 1.467(4) . ?
Fe1 Cl2 2.1790(8) . ?
Fe1 Cl1 2.1842(8) . ?
Fe1 Cl3 2.2042(8) . ?
Fe1 Cl4 2.2195(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
N1 S2 S1 99.33(9) . . ?
C10 S1 S2 91.81(10) . . ?
C1 N1 S2 115.87(19) . . ?
C1 C10 C9 122.2(2) . . ?
C1 C10 S1 116.78(19) . . ?
C9 C10 S1 121.0(2) . . ?
O2 C9 C10 122.1(2) . . ?
O2 C9 C8 122.0(2) . . ?
C10 C9 C8 115.9(2) . . ?
O1 C8 C7 124.9(3) . . ?
O1 C8 C9 116.7(3) . . ?
C7 C8 C9 118.3(2) . . ?
C6 C7 C2 118.9(3) . . ?
C6 C7 C8 118.4(2) . . ?
C2 C7 C8 122.6(2) . . ?
C5 C6 C7 120.9(3) . . ?
C6 C5 C4 119.8(3) . . ?
C3 C4 C5 120.5(3) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C2 C7 119.9(3) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 119.0(2) . . ?
N1 C1 C10 116.2(2) . . ?
N1 C1 C2 122.0(2) . . ?
C10 C1 C2 121.8(2) . . ?
Cl2 Fe1 Cl1 108.96(4) . . ?
Cl2 Fe1 Cl3 112.99(3) . . ?
Cl1 Fe1 Cl3 113.68(3) . . ?
Cl2 Fe1 Cl4 107.61(3) . . ?
Cl1 Fe1 Cl4 108.04(3) . . ?
Cl3 Fe1 Cl4 105.22(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.100




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'acetonitrile and chlorobenzene'
####################################################################### 
# 
# 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_k10194a
_database_code_depnum_ccdc_archive 'CCDC 1470546'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H24 Li4 N4 O12 S8'
_chemical_formula_sum            'C40 H24 Li4 N4 O12 S8'
_chemical_formula_weight         1036.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   15.9640(12)
_cell_length_b                   11.7083(15)
_cell_length_c                   11.632(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.590(8)
_cell_angle_gamma                90.00
_cell_volume                     2129.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    9127
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.489
# Absorption correction

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
 Sortav (Blessing 1995)
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(1)
_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  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9127
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_sigmaI/netI    0.0959
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3590
_reflns_number_gt                2072
_reflns_threshold_expression     I>2σ(I)


_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        Denzo-SMN
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'

_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)+(0.0683P)²+6.1585P] 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         3590
_refine_ls_number_parameters     307
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2085
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_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
S2a S 0.37737(13) -0.07609(16) 0.18456(16) 0.0528(5) Uani 1 1 d . . .
O2a O 0.0993(3) 0.0097(3) 0.2726(4) 0.0413(11) Uani 1 1 d . . .
N1a N 0.4006(4) 0.0017(5) 0.3049(5) 0.0450(14) Uani 1 1 d . . .
C1a C 0.3340(4) 0.0395(5) 0.3447(6) 0.0389(16) Uani 1 1 d . . .
S1a S 0.24402(13) -0.07081(16) 0.15811(15) 0.0501(5) Uani 1 1 d . . .
O1a O 0.1201(3) 0.1473(3) 0.4625(4) 0.0448(12) Uani 1 1 d . . .
C10a C 0.2490(4) 0.0107(5) 0.2860(5) 0.0344(15) Uani 1 1 d . . .
C9a C 0.1761(5) 0.0424(5) 0.3229(6) 0.0388(17) Uani 1 1 d . . .
C8a C 0.1862(4) 0.1151(5) 0.4272(6) 0.0394(16) Uani 1 1 d . . .
C7a C 0.2722(4) 0.1482(5) 0.4906(5) 0.0377(16) Uani 1 1 d . . .
C6a C 0.2825(5) 0.2158(5) 0.5962(6) 0.0488(16) Uani 1 1 d U . .
H6aA H 0.2346 0.2429 0.6251 0.059 Uiso 1 1 calc R . .
C5a C 0.3664(6) 0.2398(5) 0.6544(6) 0.0520(17) Uani 1 1 d U . .
H5aA H 0.3749 0.2813 0.7260 0.062 Uiso 1 1 calc R . .
C4a C 0.4342(5) 0.2070(6) 0.6140(6) 0.052(2) Uani 1 1 d . . .
H4aA H 0.4895 0.2285 0.6552 0.062 Uiso 1 1 calc R . .
C3a C 0.4264(5) 0.1419(5) 0.5126(6) 0.0471(18) Uani 1 1 d . . .
H3aA H 0.4760 0.1182 0.4856 0.057 Uiso 1 1 calc R . .
C2a C 0.3450(4) 0.1114(5) 0.4505(5) 0.0380(16) Uani 1 1 d . . .
S2b S 0.31770(12) -0.25583(15) 0.43002(15) 0.0490(5) Uani 1 1 d . . .
O2b O 0.0527(3) -0.1072(3) 0.5204(4) 0.0417(11) Uani 1 1 d . . .
N1b N 0.3495(4) -0.1785(4) 0.5490(4) 0.0424(14) Uani 1 1 d . . .
C1b C 0.2882(4) -0.1318(5) 0.5953(6) 0.0409(16) Uani 1 1 d . . .
S1b S 0.18545(12) -0.23904(14) 0.41431(15) 0.0456(5) Uani 1 1 d . . .
O1b O 0.0899(3) 0.0156(4) 0.7189(4) 0.0456(12) Uani 1 1 d . . .
C10b C 0.2001(4) -0.1500(5) 0.5393(5) 0.0358(15) Uani 1 1 d . . .
C9b C 0.1324(4) -0.0992(5) 0.5756(6) 0.0369(15) Uani 1 1 d . . .
C8b C 0.1512(5) -0.0309(5) 0.6835(6) 0.0392(16) Uani 1 1 d . . .
C7b C 0.2401(4) -0.0158(5) 0.7457(5) 0.0358(15) Uani 1 1 d . . .
C6b C 0.2590(5) 0.0517(6) 0.8511(5) 0.0439(15) Uani 1 1 d U . .
H6bA H 0.2144 0.0849 0.8831 0.053 Uiso 1 1 calc R . .
C5b C 0.3432(5) 0.0668(6) 0.9043(6) 0.0475(16) Uani 1 1 d U . .
H5bA H 0.3560 0.1102 0.9747 0.057 Uiso 1 1 calc R . .
C4b C 0.4085(5) 0.0229(6) 0.8612(6) 0.0502(19) Uani 1 1 d . . .
H4bA H 0.4658 0.0369 0.9001 0.060 Uiso 1 1 calc R . .
C3b C 0.3918(4) -0.0435(5) 0.7586(6) 0.0409(17) Uani 1 1 d . . .
H3bA H 0.4379 -0.0746 0.7284 0.049 Uiso 1 1 calc R . .
C2b C 0.3082(4) -0.0636(5) 0.7014(5) 0.0387(16) Uani 1 1 d . . .
Li1 Li 0.0222(7) 0.0147(9) 0.3908(10) 0.046(3) Uani 1 1 d . . .
Li2 Li -0.0234(7) -0.2384(9) 0.5086(9) 0.044(3) Uani 1 1 d . . .
O1W O -0.0332(3) -0.3003(4) 0.3552(4) 0.0598(14) Uani 1 1 d . . .
H1WA H -0.0471 -0.3624 0.3205 0.090 Uiso 1 1 d R . .
H1WB H -0.0181 -0.2656 0.2995 0.090 Uiso 1 1 d R . .
O2W O -0.0035(3) -0.3434(4) 0.6453(4) 0.0551(13) Uani 1 1 d . . .
H2WA H 0.0440 -0.3646 0.6847 0.083 Uiso 1 1 d R . .
H2WB H -0.0444 -0.3811 0.6613 0.083 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2a 0.0615(13) 0.0502(11) 0.0500(11) -0.0072(9) 0.0192(9) 0.0017(10)
O2a 0.049(3) 0.032(2) 0.045(3) 0.003(2) 0.012(2) -0.001(2)
N1a 0.046(4) 0.038(3) 0.053(4) 0.001(3) 0.012(3) -0.002(3)
C1a 0.047(5) 0.027(3) 0.045(4) 0.009(3) 0.016(3) -0.001(3)
S1a 0.0601(13) 0.0481(11) 0.0434(10) -0.0051(9) 0.0136(9) -0.0022(9)
O1a 0.051(3) 0.036(3) 0.049(3) 0.002(2) 0.013(2) 0.001(2)
C10a 0.045(4) 0.026(3) 0.034(3) 0.004(3) 0.011(3) 0.001(3)
C9a 0.052(5) 0.021(3) 0.045(4) 0.011(3) 0.012(3) -0.002(3)
C8a 0.044(5) 0.034(4) 0.041(4) 0.009(3) 0.010(3) -0.001(3)
C7a 0.053(5) 0.024(3) 0.038(4) 0.002(3) 0.014(3) 0.000(3)
C6a 0.071(4) 0.030(3) 0.047(4) 0.017(3) 0.014(3) -0.001(3)
C5a 0.086(5) 0.027(3) 0.042(4) 0.004(3) 0.011(3) 0.000(3)
C4a 0.060(5) 0.035(4) 0.054(5) 0.014(4) -0.007(4) -0.011(4)
C3a 0.051(5) 0.036(4) 0.052(4) 0.000(3) 0.004(4) -0.002(3)
C2a 0.052(5) 0.025(3) 0.036(4) 0.011(3) 0.006(3) 0.003(3)
S2b 0.0622(13) 0.0421(10) 0.0455(11) -0.0044(8) 0.0176(9) 0.0049(9)
O2b 0.052(3) 0.036(3) 0.039(3) 0.002(2) 0.011(2) 0.003(2)
N1b 0.050(4) 0.037(3) 0.040(3) 0.003(3) 0.011(3) 0.001(3)
C1b 0.046(5) 0.034(4) 0.047(4) 0.012(3) 0.019(3) 0.006(3)
S1b 0.0592(13) 0.0373(10) 0.0409(10) -0.0039(8) 0.0117(8) 0.0012(9)
O1b 0.049(3) 0.048(3) 0.041(3) -0.005(2) 0.011(2) 0.003(2)
C10b 0.042(4) 0.032(4) 0.034(4) 0.010(3) 0.007(3) -0.003(3)
C9b 0.039(4) 0.030(3) 0.043(4) 0.006(3) 0.010(3) 0.000(3)
C8b 0.048(5) 0.033(4) 0.039(4) 0.005(3) 0.013(3) -0.001(3)
C7b 0.046(4) 0.031(3) 0.031(4) 0.000(3) 0.010(3) -0.003(3)
C6b 0.053(4) 0.042(3) 0.037(3) 0.014(3) 0.009(3) -0.004(3)
C5b 0.067(4) 0.036(3) 0.036(3) 0.004(3) 0.000(3) -0.006(3)
C4b 0.044(5) 0.050(4) 0.053(5) 0.016(4) 0.000(4) -0.011(4)
C3b 0.047(5) 0.037(4) 0.040(4) 0.010(3) 0.010(3) 0.003(3)
C2b 0.044(4) 0.031(3) 0.040(4) 0.006(3) 0.007(3) -0.002(3)
Li1 0.049(8) 0.040(6) 0.048(7) 0.006(5) 0.006(5) 0.009(5)
Li2 0.053(8) 0.036(6) 0.039(6) 0.002(5) 0.000(5) 0.002(5)
O1W 0.091(4) 0.043(3) 0.046(3) -0.010(2) 0.014(3) -0.015(3)
O2W 0.055(3) 0.048(3) 0.063(3) 0.012(2) 0.014(3) 0.004(2)

_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
S2a N1a 1.648(6) . ?
S2a S1a 2.090(3) . ?
O2a C9a 1.305(8) . ?
O2a Li1 2.023(12) . ?
N1a C1a 1.319(8) . ?
C1a C10a 1.431(9) . ?
C1a C2a 1.472(9) . ?
S1a C10a 1.756(6) . ?
O1a C8a 1.264(7) . ?
O1a Li2 1.961(12) 3_556 ?
O1a Li1 2.242(12) . ?
C10a C9a 1.370(9) . ?
C9a C8a 1.464(9) . ?
C9a Li1 2.747(14) . ?
C8a C7a 1.474(9) . ?
C7a C2a 1.404(9) . ?
C7a C6a 1.443(9) . ?
C6a C5a 1.403(10) . ?
C5a C4a 1.320(10) . ?
C4a C3a 1.389(9) . ?
C3a C2a 1.401(9) . ?
S2b N1b 1.646(5) . ?
S2b S1b 2.092(3) . ?
O2b C9b 1.307(7) . ?
O2b Li2 1.946(12) . ?
O2b Li1 2.041(12) 3_556 ?
O2b Li1 2.063(11) . ?
N1b C1b 1.326(8) . ?
C1b C10b 1.443(9) . ?
C1b C2b 1.451(9) . ?
S1b C10b 1.767(6) . ?
O1b C8b 1.259(7) . ?
O1b Li1 2.009(12) 3_556 ?
C10b C9b 1.372(9) . ?
C9b C8b 1.467(9) . ?
C9b Li1 2.758(13) 3_556 ?
C8b C7b 1.468(9) . ?
C8b Li1 2.735(13) 3_556 ?
C7b C2b 1.409(9) . ?
C7b C6b 1.438(9) . ?
C6b C5b 1.374(9) . ?
C5b C4b 1.346(10) . ?
C4b C3b 1.404(9) . ?
C3b C2b 1.387(9) . ?
Li1 O1b 2.009(12) 3_556 ?
Li1 O2b 2.041(12) 3_556 ?
Li1 C8b 2.735(13) 3_556 ?
Li1 C9b 2.758(13) 3_556 ?
Li1 Li1 2.79(2) 3_556 ?
Li1 Li2 2.867(15) 3_556 ?
Li1 Li2 3.405(15) . ?
Li2 O1W 1.903(11) . ?
Li2 O1a 1.961(12) 3_556 ?
Li2 O2W 1.984(11) . ?
Li2 Li1 2.867(16) 3_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1a S2a S1a 99.1(2) . . ?
C9a O2a Li1 109.4(5) . . ?
C1a N1a S2a 115.1(5) . . ?
N1a C1a C10a 120.5(6) . . ?
N1a C1a C2a 121.1(6) . . ?
C10a C1a C2a 118.4(6) . . ?
C10a S1a S2a 91.1(2) . . ?
C8a O1a Li2 162.8(5) . 3_556 ?
C8a O1a Li1 103.8(5) . . ?
Li2 O1a Li1 85.8(5) 3_556 . ?
C9a C10a C1a 124.8(6) . . ?
C9a C10a S1a 121.1(5) . . ?
C1a C10a S1a 114.2(5) . . ?
O2a C9a C10a 124.1(6) . . ?
O2a C9a C8a 118.6(6) . . ?
C10a C9a C8a 117.3(6) . . ?
C10a C9a Li1 157.4(5) . . ?
C8a C9a Li1 77.6(5) . . ?
O1a C8a C9a 118.9(6) . . ?
O1a C8a C7a 120.9(6) . . ?
C9a C8a C7a 120.2(6) . . ?
C2a C7a C6a 119.4(6) . . ?
C2a C7a C8a 120.3(6) . . ?
C6a C7a C8a 120.3(6) . . ?
C5a C6a C7a 117.1(7) . . ?
C4a C5a C6a 122.8(7) . . ?
C5a C4a C3a 121.5(7) . . ?
C4a C3a C2a 119.5(7) . . ?
C3a C2a C7a 119.7(6) . . ?
C3a C2a C1a 121.3(6) . . ?
C7a C2a C1a 119.0(6) . . ?
N1b S2b S1b 99.0(2) . . ?
C9b O2b Li2 128.5(5) . . ?
C9b O2b Li1 108.9(5) . 3_556 ?
Li2 O2b Li1 91.9(5) . 3_556 ?
C9b O2b Li1 111.9(5) . . ?
Li2 O2b Li1 116.2(5) . . ?
Li1 O2b Li1 85.7(5) 3_556 . ?
C1b N1b S2b 116.1(5) . . ?
N1b C1b C10b 119.2(6) . . ?
N1b C1b C2b 121.3(6) . . ?
C10b C1b C2b 119.5(6) . . ?
C10b S1b S2b 91.1(2) . . ?
C8b O1b Li1 111.6(5) . 3_556 ?
C9b C10b C1b 123.7(6) . . ?
C9b C10b S1b 121.8(5) . . ?
C1b C10b S1b 114.4(5) . . ?
O2b C9b C10b 124.5(6) . . ?
O2b C9b C8b 118.1(6) . . ?
C10b C9b C8b 117.4(6) . . ?
C10b C9b Li1 168.9(6) . 3_556 ?
C8b C9b Li1 73.7(5) . 3_556 ?
O1b C8b C9b 118.4(6) . . ?
O1b C8b C7b 121.6(6) . . ?
C9b C8b C7b 119.9(6) . . ?
C9b C8b Li1 75.3(5) . 3_556 ?
C7b C8b Li1 164.5(5) . 3_556 ?
C2b C7b C6b 119.0(6) . . ?
C2b C7b C8b 120.8(6) . . ?
C6b C7b C8b 120.2(6) . . ?
C5b C6b C7b 118.2(7) . . ?
C4b C5b C6b 122.9(7) . . ?
C5b C4b C3b 120.0(7) . . ?
C2b C3b C4b 120.1(6) . . ?
C3b C2b C7b 119.7(6) . . ?
C3b C2b C1b 121.8(6) . . ?
C7b C2b C1b 118.4(6) . . ?
O1b Li1 O2a 98.6(5) 3_556 . ?
O1b Li1 O2b 83.0(5) 3_556 3_556 ?
O2a Li1 O2b 149.1(6) . 3_556 ?
O1b Li1 O2b 113.0(6) 3_556 . ?
O2a Li1 O2b 112.9(5) . . ?
O2b Li1 O2b 94.3(5) 3_556 . ?
O1b Li1 O1a 145.5(6) 3_556 . ?
O2a Li1 O1a 78.4(4) . . ?
O2b Li1 O1a 83.1(4) 3_556 . ?
O2b Li1 O1a 99.4(5) . . ?
O1b Li1 C8b 25.4(2) 3_556 3_556 ?
O2a Li1 C8b 120.2(5) . 3_556 ?
O2b Li1 C8b 57.6(3) 3_556 3_556 ?
O2b Li1 C8b 110.8(5) . 3_556 ?
O1a Li1 C8b 131.0(5) . 3_556 ?
O1b Li1 C9a 124.9(5) 3_556 . ?
O2a Li1 C9a 26.6(2) . . ?
O2b Li1 C9a 137.0(6) 3_556 . ?
O2b Li1 C9a 101.4(5) . . ?
O1a Li1 C9a 55.1(3) . . ?
C8b Li1 C9a 143.9(5) 3_556 . ?
O1b Li1 C9b 56.3(3) 3_556 3_556 ?
O2a Li1 C9b 142.3(5) . 3_556 ?
O2b Li1 C9b 26.7(2) 3_556 3_556 ?
O2b Li1 C9b 103.4(5) . 3_556 ?
O1a Li1 C9b 106.0(4) . 3_556 ?
C8b Li1 C9b 31.0(2) 3_556 3_556 ?
C9a Li1 C9b 151.1(5) . 3_556 ?
O1b Li1 Li1 101.5(6) 3_556 3_556 ?
O2a Li1 Li1 156.2(8) . 3_556 ?
O2b Li1 Li1 47.5(4) 3_556 3_556 ?
O2b Li1 Li1 46.8(3) . 3_556 ?
O1a Li1 Li1 91.9(6) . 3_556 ?
C8b Li1 Li1 82.6(5) 3_556 3_556 ?
C9a Li1 Li1 132.9(7) . 3_556 ?
C9b Li1 Li1 61.2(4) 3_556 3_556 ?
O1b Li1 Li2 110.7(5) 3_556 3_556 ?
O2a Li1 Li2 110.4(5) . 3_556 ?
O2b Li1 Li2 42.7(3) 3_556 3_556 ?
O2b Li1 Li2 110.7(5) . 3_556 ?
O1a Li1 Li2 43.0(3) . 3_556 ?
C8b Li1 Li2 89.4(4) 3_556 3_556 ?
C9a Li1 Li2 94.4(4) . 3_556 ?
C9b Li1 Li2 63.1(4) 3_556 3_556 ?
Li1 Li1 Li2 74.0(5) 3_556 3_556 ?
O1b Li1 Li2 82.3(4) 3_556 . ?
O2a Li1 Li2 117.2(5) . . ?
O2b Li1 Li2 93.7(4) 3_556 . ?
O2b Li1 Li2 30.8(3) . . ?
O1a Li1 Li2 130.0(5) . . ?
C8b Li1 Li2 84.4(4) 3_556 . ?
C9a Li1 Li2 119.6(4) . . ?
C9b Li1 Li2 89.2(4) 3_556 . ?
Li1 Li1 Li2 54.0(4) 3_556 . ?
Li2 Li1 Li2 128.0(4) 3_556 . ?
O1W Li2 O2b 107.4(6) . . ?
O1W Li2 O1a 116.6(6) . 3_556 ?
O2b Li2 O1a 93.5(5) . 3_556 ?
O1W Li2 O2W 119.1(6) . . ?
O2b Li2 O2W 115.8(6) . . ?
O1a Li2 O2W 101.8(5) 3_556 . ?
O1W Li2 Li1 136.3(5) . 3_556 ?
O2b Li2 Li1 45.4(3) . 3_556 ?
O1a Li2 Li1 51.2(4) 3_556 3_556 ?
O2W Li2 Li1 104.6(5) . 3_556 ?
O1W Li2 Li1 86.4(4) . . ?
O2b Li2 Li1 32.9(3) . . ?
O1a Li2 Li1 80.5(4) 3_556 . ?
O2W Li2 Li1 148.1(5) . . ?
Li1 Li2 Li1 52.0(4) 3_556 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O2a 0.84 1.94 2.765(6) 168.9 2_545
O1W H1WB O2W 0.84 2.25 3.079(6) 168.6 4
O2W H2WA O2a 0.84 2.09 2.774(6) 139.0 4_556
O2W H2WB O1b 0.84 2.08 2.828(6) 147.6 2_546

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.087
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'methanol and toluene'
####################################################################### 
# 
# 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_k10144
_database_code_depnum_ccdc_archive 'CCDC 1470547'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
4-hydroxy-naphtho[1,2-d][1,2,3]dithiazol-5-one
_chemical_name_common            ?
_chemical_melting_point          515-517
_chemical_formula_moiety         'C10 H5 N O2 S2'
_chemical_formula_sum            'C10 H5 N O2 S2'
_chemical_formula_weight         235.27

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   15.2462(14)
_cell_length_b                   3.8351(2)
_cell_length_c                   16.5627(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.361(3)
_cell_angle_gamma                90.00
_cell_volume                     907.92(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    4547
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.558
# Absorption correction 

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(1)
_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  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            5307
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_sigmaI/netI    0.1034
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2037
_reflns_number_gt                1133
_reflns_threshold_expression     I>2σ(I)


_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        Denzo-SMN
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'

_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)+(0.0592P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2037
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_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 0.29274(7) 0.0852(2) 0.66923(6) 0.0333(3) Uani 1 1 d . . .
S2 S 0.14717(8) 0.0407(2) 0.63787(7) 0.0356(3) Uani 1 1 d . . .
O1 O 0.39908(19) 0.6118(7) 0.43779(18) 0.0381(7) Uani 1 1 d . . .
O2 O 0.4386(2) 0.3067(7) 0.59693(18) 0.0375(7) Uani 1 1 d . . .
H2 H 0.484(3) 0.353(11) 0.574(3) 0.061(15) Uiso 1 1 d . . .
N1 N 0.1144(2) 0.2129(7) 0.5414(2) 0.0321(8) Uani 1 1 d . . .
C1 C 0.1812(3) 0.3192(8) 0.5146(2) 0.0250(9) Uani 1 1 d . . .
C2 C 0.1604(3) 0.4818(9) 0.4302(2) 0.0274(9) Uani 1 1 d . . .
C3 C 0.0683(3) 0.5347(9) 0.3748(3) 0.0303(9) Uani 1 1 d . . .
H3A H 0.0176 0.4657 0.3920 0.036 Uiso 1 1 calc R . .
C4 C 0.0508(3) 0.6873(9) 0.2950(2) 0.0327(10) Uani 1 1 d . . .
H4A H -0.0118 0.7215 0.2574 0.039 Uiso 1 1 calc R . .
C5 C 0.1249(3) 0.7907(9) 0.2697(3) 0.0330(10) Uani 1 1 d . . .
H5A H 0.1129 0.8938 0.2148 0.040 Uiso 1 1 calc R . .
C6 C 0.2153(3) 0.7435(8) 0.3243(2) 0.0282(9) Uani 1 1 d . . .
H6A H 0.2656 0.8200 0.3074 0.034 Uiso 1 1 calc R . .
C7 C 0.2343(3) 0.5842(8) 0.4046(2) 0.0244(9) Uani 1 1 d . . .
C8 C 0.3323(3) 0.5272(9) 0.4601(3) 0.0292(9) Uani 1 1 d . . .
C9 C 0.3502(3) 0.3639(9) 0.5440(2) 0.0288(9) Uani 1 1 d . . .
C10 C 0.2781(3) 0.2707(8) 0.5692(2) 0.0253(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0404(7) 0.0307(6) 0.0291(6) 0.0027(4) 0.0126(5) 0.0012(4)
S2 0.0433(7) 0.0319(6) 0.0358(7) 0.0023(4) 0.0191(5) -0.0035(5)
O1 0.0269(17) 0.0531(18) 0.0348(18) 0.0059(13) 0.0116(14) -0.0025(13)
O2 0.0258(18) 0.0544(17) 0.0289(17) 0.0050(13) 0.0051(15) -0.0015(14)
N1 0.036(2) 0.0291(17) 0.033(2) 0.0003(14) 0.0139(17) -0.0024(14)
C1 0.028(2) 0.0190(17) 0.030(2) -0.0040(16) 0.0137(19) -0.0026(15)
C2 0.029(2) 0.0239(18) 0.029(2) -0.0034(16) 0.0107(19) -0.0012(16)
C3 0.027(2) 0.0293(19) 0.037(3) -0.0028(17) 0.014(2) -0.0017(17)
C4 0.034(3) 0.034(2) 0.026(2) -0.0016(18) 0.0047(19) 0.0050(18)
C5 0.037(3) 0.031(2) 0.031(2) -0.0002(17) 0.012(2) 0.0002(18)
C6 0.031(3) 0.026(2) 0.032(2) -0.0032(17) 0.015(2) 0.0003(16)
C7 0.030(2) 0.0232(19) 0.019(2) -0.0056(15) 0.0067(18) -0.0033(15)
C8 0.035(3) 0.0271(19) 0.028(2) -0.0011(16) 0.014(2) -0.0009(17)
C9 0.029(3) 0.029(2) 0.028(2) -0.0005(17) 0.008(2) -0.0011(17)
C10 0.032(2) 0.0199(19) 0.022(2) -0.0047(15) 0.0076(18) 0.0007(15)

_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 C10 1.744(4) . ?
S1 S2 2.1030(16) . ?
S2 N1 1.638(3) . ?
O1 C8 1.241(4) . ?
O2 C9 1.347(5) . ?
N1 C1 1.310(5) . ?
C1 C10 1.451(5) . ?
C1 C2 1.461(5) . ?
C2 C7 1.391(5) . ?
C2 C3 1.400(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.391(5) . ?
C5 C6 1.372(5) . ?
C6 C7 1.399(5) . ?
C7 C8 1.473(5) . ?
C8 C9 1.460(5) . ?
C9 C10 1.352(5) . ?

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
C10 S1 S2 91.35(14) . . ?
N1 S2 S1 98.40(13) . . ?
C1 N1 S2 116.5(3) . . ?
N1 C1 C10 119.5(3) . . ?
N1 C1 C2 121.4(4) . . ?
C10 C1 C2 119.1(3) . . ?
C7 C2 C3 119.6(4) . . ?
C7 C2 C1 118.9(4) . . ?
C3 C2 C1 121.5(4) . . ?
C4 C3 C2 120.2(4) . . ?
C3 C4 C5 120.0(4) . . ?
C6 C5 C4 119.9(4) . . ?
C5 C6 C7 120.8(4) . . ?
C2 C7 C6 119.4(4) . . ?
C2 C7 C8 121.4(3) . . ?
C6 C7 C8 119.2(3) . . ?
O1 C8 C9 119.7(4) . . ?
O1 C8 C7 122.3(3) . . ?
C9 C8 C7 118.0(3) . . ?
O2 C9 C10 119.5(4) . . ?
O2 C9 C8 120.2(3) . . ?
C10 C9 C8 120.3(4) . . ?
C9 C10 C1 122.3(3) . . ?
C9 C10 S1 123.5(3) . . ?
C1 C10 S1 114.2(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.91(5) 1.87(5) 2.746(4) 161(4) 3_666

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.102

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'methylene chloride'
####################################################################### 
# 
# 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_cs54
_database_code_depnum_ccdc_archive 'CCDC 1471457'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_cs54                
;
PROBLEM: Short Inter HL..A  Contact Cl1    ..  S1      ..       2.97 Ang.  
RESPONSE: This is expected for this type of structure. It is somewhere in 
between an ionic complex [1+][Cl-] and a covalent bonded species. We know 
this because we can perform metathesis to exchange the Cl-, but it also has 
solubility in organic solvents. It is similar to other structures of 
thiazolium chlorides
;
_vrf_PLAT430_cs54                
;
PROBLEM: Short Inter D...A Contact  S2     ..  O1      ..       2.86 Ang.  
RESPONSE:There are electrostatic contacts between S(delta positive) and O.
;
# end Validation Reply Form  

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'4,5-dioxo-naphtho[1,2-d][1,2,3]dithiazol-2-ium chloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N O2 S2, Cl'
_chemical_formula_sum            'C10 H4 Cl N O2 S2'
_chemical_formula_weight         269.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'

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

_cell_length_a                   19.620(5)
_cell_length_b                   5.8942(15)
_cell_length_c                   8.422(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     974.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1176
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      23.50

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7449
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9076
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.03
_reflns_number_total             945
_reflns_number_gt                747
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0492P)²+1.1136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_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         945
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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
Cl1 Cl 0.84994(6) 0.2500 0.26906(14) 0.0281(3) Uani 1 2 d S . .
S1 S 0.75046(6) 0.2500 0.53473(15) 0.0251(3) Uani 1 2 d S . .
S2 S 0.69710(6) 0.2500 0.32844(14) 0.0247(3) Uani 1 2 d S . .
N1 N 0.62191(18) 0.2500 0.4022(5) 0.0227(8) Uani 1 2 d S . .
C1 C 0.6174(2) 0.2500 0.5611(5) 0.0220(10) Uani 1 2 d S . .
C10 C 0.6795(2) 0.2500 0.6448(5) 0.0211(10) Uani 1 2 d S . .
C9 C 0.6821(2) 0.2500 0.8194(5) 0.0215(10) Uani 1 2 d S . .
C8 C 0.6141(2) 0.2500 0.9054(6) 0.0258(10) Uani 1 2 d S . .
C7 C 0.5509(2) 0.2500 0.8100(5) 0.0227(10) Uani 1 2 d S . .
C6 C 0.4882(2) 0.2500 0.8883(6) 0.0280(11) Uani 1 2 d S . .
H6A H 0.4871 0.2500 1.0010 0.034 Uiso 1 2 calc SR . .
C5 C 0.4288(2) 0.2500 0.8054(6) 0.0315(12) Uani 1 2 d S . .
H5A H 0.3865 0.2500 0.8604 0.038 Uiso 1 2 calc SR . .
C4 C 0.4297(2) 0.2500 0.6397(6) 0.0286(11) Uani 1 2 d S . .
H4A H 0.3881 0.2500 0.5818 0.034 Uiso 1 2 calc SR . .
C3 C 0.4911(2) 0.2500 0.5602(6) 0.0262(11) Uani 1 2 d S . .
H3A H 0.4916 0.2500 0.4474 0.031 Uiso 1 2 calc SR . .
C2 C 0.5523(2) 0.2500 0.6431(5) 0.0201(10) Uani 1 2 d S . .
O2 O 0.73643(15) 0.2500 0.8917(4) 0.0288(8) Uani 1 2 d S . .
O1 O 0.61383(17) 0.2500 1.0505(4) 0.0363(9) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0268(6) 0.0257(6) 0.0320(7) 0.000 0.0083(5) 0.000
S1 0.0186(6) 0.0268(6) 0.0299(7) 0.000 -0.0001(5) 0.000
S2 0.0250(6) 0.0251(6) 0.0240(6) 0.000 0.0025(5) 0.000
N1 0.023(2) 0.0213(19) 0.024(2) 0.000 -0.0003(16) 0.000
C1 0.027(3) 0.011(2) 0.028(3) 0.000 0.001(2) 0.000
C10 0.021(2) 0.013(2) 0.029(3) 0.000 -0.002(2) 0.000
C9 0.024(3) 0.011(2) 0.030(3) 0.000 -0.004(2) 0.000
C8 0.036(3) 0.019(2) 0.023(3) 0.000 -0.003(2) 0.000
C7 0.023(2) 0.016(2) 0.029(3) 0.000 0.003(2) 0.000
C6 0.035(3) 0.019(2) 0.030(3) 0.000 0.012(2) 0.000
C5 0.017(2) 0.019(2) 0.058(4) 0.000 0.005(2) 0.000
C4 0.020(2) 0.020(2) 0.045(3) 0.000 0.001(2) 0.000
C3 0.028(3) 0.017(2) 0.034(3) 0.000 -0.007(2) 0.000
C2 0.019(2) 0.015(2) 0.026(3) 0.000 0.0004(19) 0.000
O2 0.0279(19) 0.0208(16) 0.038(2) 0.000 -0.0080(16) 0.000
O1 0.046(2) 0.042(2) 0.021(2) 0.000 -0.0005(16) 0.000

_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 C10 1.673(5) . ?
S1 S2 2.0285(18) . ?
S2 N1 1.601(4) . ?
N1 C1 1.341(6) . ?
C1 C10 1.407(6) . ?
C1 C2 1.452(6) . ?
C10 C9 1.471(6) . ?
C9 O2 1.227(5) . ?
C9 C8 1.518(6) . ?
C8 O1 1.221(6) . ?
C8 C7 1.479(6) . ?
C7 C6 1.395(6) . ?
C7 C2 1.405(6) . ?
C6 C5 1.360(7) . ?
C6 H6A 0.9500 . ?
C5 C4 1.396(7) . ?
C5 H5A 0.9500 . ?
C4 C3 1.378(6) . ?
C4 H4A 0.9500 . ?
C3 C2 1.390(6) . ?
C3 H3A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 S2 92.58(16) . . ?
N1 S2 S1 98.23(15) . . ?
C1 N1 S2 116.6(3) . . ?
N1 C1 C10 116.3(4) . . ?
N1 C1 C2 122.2(4) . . ?
C10 C1 C2 121.5(4) . . ?
C1 C10 C9 122.1(4) . . ?
C1 C10 S1 116.3(4) . . ?
C9 C10 S1 121.7(3) . . ?
O2 C9 C10 121.7(4) . . ?
O2 C9 C8 121.7(4) . . ?
C10 C9 C8 116.5(4) . . ?
O1 C8 C7 122.6(5) . . ?
O1 C8 C9 118.8(4) . . ?
C7 C8 C9 118.5(4) . . ?
C6 C7 C2 119.3(4) . . ?
C6 C7 C8 118.9(4) . . ?
C2 C7 C8 121.8(4) . . ?
C5 C6 C7 120.9(5) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C2 C7 119.1(4) . . ?
C3 C2 C1 121.4(4) . . ?
C7 C2 C1 119.6(4) . . ?

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
C10 S1 S2 N1 0.0 . . . . ?
S1 S2 N1 C1 0.0 . . . . ?
S2 N1 C1 C10 0.0 . . . . ?
S2 N1 C1 C2 180.0 . . . . ?
N1 C1 C10 C9 180.0 . . . . ?
C2 C1 C10 C9 0.0 . . . . ?
N1 C1 C10 S1 0.0 . . . . ?
C2 C1 C10 S1 180.0 . . . . ?
S2 S1 C10 C1 0.0 . . . . ?
S2 S1 C10 C9 180.0 . . . . ?
C1 C10 C9 O2 180.0 . . . . ?
S1 C10 C9 O2 0.0 . . . . ?
C1 C10 C9 C8 0.0 . . . . ?
S1 C10 C9 C8 180.0 . . . . ?
O2 C9 C8 O1 0.000(1) . . . . ?
C10 C9 C8 O1 180.0 . . . . ?
O2 C9 C8 C7 180.0 . . . . ?
C10 C9 C8 C7 0.000(1) . . . . ?
O1 C8 C7 C6 0.000(1) . . . . ?
C9 C8 C7 C6 180.0 . . . . ?
O1 C8 C7 C2 180.000(1) . . . . ?
C9 C8 C7 C2 0.000(1) . . . . ?
C2 C7 C6 C5 0.000(1) . . . . ?
C8 C7 C6 C5 180.000(1) . . . . ?
C7 C6 C5 C4 0.000(1) . . . . ?
C6 C5 C4 C3 0.000(1) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C7 0.0 . . . . ?
C4 C3 C2 C1 180.0 . . . . ?
C6 C7 C2 C3 0.000(1) . . . . ?
C8 C7 C2 C3 180.0 . . . . ?
C6 C7 C2 C1 180.0 . . . . ?
C8 C7 C2 C1 0.000(1) . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
C10 C1 C2 C3 180.0 . . . . ?
N1 C1 C2 C7 180.0 . . . . ?
C10 C1 C2 C7 0.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.092








_exptl_crystal_recrystallization_method 
'single crystal recovered from crude product'
####################################################################### 
# 
# 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_chad2_0m
_database_code_depnum_ccdc_archive 'CCDC 1471458'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_chad2_0m            
;
PROBLEM: Short Inter HL..A  Contact Cl2    ..  S2      ..       3.17 Ang.  
RESPONSE: This is expected for this type of structure as it is somewhere 
between an ionic and covalent species. There are electrostatic contacts 
between S(delta positive) and Cl-.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'4,5-dioxo-naphtho[1,2-d][1,2,3]dithiazol-2-ium tetrachlorogallatel'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N O2 S2, Cl4 Ga'
_chemical_formula_sum            'C10 H4 Cl4 Ga N O2 S2'
_chemical_formula_weight         445.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.0862(15)
_cell_length_b                   9.4172(18)
_cell_length_c                   19.659(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.079(4)
_cell_angle_gamma                90.00
_cell_volume                     1497.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2760
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.37

_exptl_crystal_description       needle
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5180
_exptl_absorpt_correction_T_max  0.8953
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
Alert B, short contacts: This is expected for this type of
structure as it is somewhere between an ionic and covalent species. 
There are electrostatic contacts between S(delta positive) and Cl 
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17035
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.46
_reflns_number_total             3088
_reflns_number_gt                2503
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0184P)²+0.7886P] 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         3088
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0580
_refine_ls_wR_factor_gt          0.0529
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.50868(8) 0.93288(7) 0.73741(4) 0.02065(16) Uani 1 1 d . . .
S2 S 0.59639(8) 0.77731(8) 0.67654(4) 0.02096(16) Uani 1 1 d . . .
N1 N 0.4465(3) 0.7647(2) 0.62503(11) 0.0184(5) Uani 1 1 d . . .
C1 C 0.3194(3) 0.8509(3) 0.63688(14) 0.0160(6) Uani 1 1 d . . .
C2 C 0.1691(3) 0.8435(3) 0.59507(13) 0.0165(6) Uani 1 1 d . . .
C3 C 0.1540(3) 0.7414(3) 0.54482(14) 0.0191(6) Uani 1 1 d . . .
H3A H 0.2431 0.6786 0.5356 0.023 Uiso 1 1 calc R . .
C4 C 0.0084(3) 0.7313(3) 0.50798(15) 0.0230(6) Uani 1 1 d . . .
H4A H -0.0024 0.6607 0.4737 0.028 Uiso 1 1 calc R . .
C5 C -0.1210(3) 0.8227(3) 0.52068(15) 0.0251(7) Uani 1 1 d . . .
H5A H -0.2211 0.8137 0.4957 0.030 Uiso 1 1 calc R . .
C6 C -0.1058(3) 0.9272(3) 0.56944(14) 0.0214(6) Uani 1 1 d . . .
H6A H -0.1943 0.9915 0.5771 0.026 Uiso 1 1 calc R . .
C7 C 0.0390(3) 0.9384(3) 0.60748(14) 0.0180(6) Uani 1 1 d . . .
O1 O -0.0535(2) 1.1380(2) 0.67007(11) 0.0353(5) Uani 1 1 d . . .
C8 C 0.0505(3) 1.0486(3) 0.66044(15) 0.0217(6) Uani 1 1 d . . .
O2 O 0.2188(2) 1.1375(2) 0.75175(10) 0.0253(5) Uani 1 1 d . . .
C9 C 0.2052(3) 1.0514(3) 0.70703(14) 0.0190(6) Uani 1 1 d . . .
C10 C 0.3332(3) 0.9447(3) 0.69177(14) 0.0169(6) Uani 1 1 d . . .
Ga1 Ga 0.97815(3) 0.84151(3) 0.872496(16) 0.01956(9) Uani 1 1 d . . .
Cl1 Cl 0.79686(9) 0.99049(8) 0.90953(5) 0.0360(2) Uani 1 1 d . . .
Cl2 Cl 0.92347(8) 0.80504(8) 0.76437(4) 0.03028(18) Uani 1 1 d . . .
Cl3 Cl 1.23042(8) 0.91705(8) 0.87842(4) 0.02633(17) Uani 1 1 d . . .
Cl4 Cl 0.97279(8) 0.64134(7) 0.92747(4) 0.02339(16) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0220(3) 0.0200(4) 0.0199(4) -0.0009(3) -0.0054(3) 0.0005(3)
S2 0.0173(3) 0.0225(4) 0.0231(4) -0.0009(3) -0.0039(3) 0.0029(3)
N1 0.0154(11) 0.0208(13) 0.0190(13) 0.0014(10) -0.0010(9) 0.0007(9)
C1 0.0162(12) 0.0143(14) 0.0173(15) 0.0039(11) 0.0014(11) -0.0001(10)
C2 0.0172(12) 0.0182(14) 0.0141(15) 0.0052(12) 0.0021(11) -0.0002(11)
C3 0.0206(13) 0.0187(15) 0.0178(15) 0.0017(12) -0.0013(11) 0.0038(11)
C4 0.0252(14) 0.0240(16) 0.0197(16) 0.0003(13) -0.0039(12) -0.0013(12)
C5 0.0191(14) 0.0325(18) 0.0238(17) 0.0045(14) -0.0043(12) -0.0036(12)
C6 0.0175(13) 0.0233(16) 0.0233(17) 0.0055(13) 0.0015(12) 0.0034(11)
C7 0.0179(13) 0.0189(15) 0.0173(15) 0.0030(12) 0.0023(11) 0.0006(11)
O1 0.0331(11) 0.0354(13) 0.0373(14) -0.0097(11) -0.0046(10) 0.0168(10)
C8 0.0220(14) 0.0214(16) 0.0216(17) 0.0007(13) 0.0023(12) 0.0042(12)
O2 0.0313(11) 0.0207(11) 0.0239(12) -0.0052(9) -0.0007(9) 0.0023(8)
C9 0.0223(13) 0.0171(15) 0.0176(16) 0.0031(13) 0.0020(11) 0.0007(11)
C10 0.0191(13) 0.0146(14) 0.0171(15) 0.0038(12) -0.0008(11) -0.0014(11)
Ga1 0.01847(15) 0.01949(17) 0.02072(18) 0.00180(14) -0.00028(12) -0.00002(12)
Cl1 0.0344(4) 0.0233(4) 0.0503(6) 0.0071(4) 0.0188(4) 0.0060(3)
Cl2 0.0263(4) 0.0408(5) 0.0236(4) 0.0039(3) -0.0080(3) -0.0041(3)
Cl3 0.0221(3) 0.0307(4) 0.0262(4) 0.0020(3) -0.0026(3) -0.0068(3)
Cl4 0.0235(3) 0.0190(4) 0.0276(4) 0.0032(3) -0.0025(3) -0.0028(3)

_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 C10 1.681(3) . ?
S1 S2 2.0208(10) . ?
S2 N1 1.583(2) . ?
N1 C1 1.330(3) . ?
C1 C10 1.399(4) . ?
C1 C2 1.468(3) . ?
C2 C3 1.384(4) . ?
C2 C7 1.402(4) . ?
C3 C4 1.385(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.379(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.392(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.473(4) . ?
O1 C8 1.204(3) . ?
C8 C9 1.550(4) . ?
O2 C9 1.201(3) . ?
C9 C10 1.474(4) . ?
Ga1 Cl1 2.1565(8) . ?
Ga1 Cl2 2.1974(9) . ?
Ga1 Cl3 2.1633(8) . ?
Ga1 Cl4 2.1733(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
C10 S1 S2 91.64(10) . . ?
N1 S2 S1 99.45(9) . . ?
C1 N1 S2 115.65(19) . . ?
N1 C1 C10 117.4(2) . . ?
N1 C1 C2 120.8(2) . . ?
C10 C1 C2 121.8(2) . . ?
C3 C2 C7 120.1(2) . . ?
C3 C2 C1 120.3(2) . . ?
C7 C2 C1 119.6(2) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C6 C7 C2 119.2(3) . . ?
C6 C7 C8 119.1(2) . . ?
C2 C7 C8 121.7(2) . . ?
O1 C8 C7 124.0(2) . . ?
O1 C8 C9 117.3(2) . . ?
C7 C8 C9 118.7(2) . . ?
O2 C9 C10 123.1(2) . . ?
O2 C9 C8 121.1(2) . . ?
C10 C9 C8 115.8(2) . . ?
C1 C10 C9 122.2(2) . . ?
C1 C10 S1 115.85(19) . . ?
C9 C10 S1 121.9(2) . . ?
Cl1 Ga1 Cl2 107.00(3) . . ?
Cl1 Ga1 Cl3 114.16(4) . . ?
Cl1 Ga1 Cl4 112.48(3) . . ?
Cl3 Ga1 Cl4 106.13(3) . . ?
Cl3 Ga1 Cl2 106.97(3) . . ?
Cl4 Ga1 Cl2 109.96(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
C10 S1 S2 N1 -0.09(13) . . . . ?
S1 S2 N1 C1 -0.7(2) . . . . ?
S2 N1 C1 C10 1.5(3) . . . . ?
S2 N1 C1 C2 -176.5(2) . . . . ?
N1 C1 C2 C3 3.4(4) . . . . ?
C10 C1 C2 C3 -174.5(3) . . . . ?
N1 C1 C2 C7 -178.2(2) . . . . ?
C10 C1 C2 C7 3.9(4) . . . . ?
C7 C2 C3 C4 -1.5(4) . . . . ?
C1 C2 C3 C4 176.9(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C7 -1.8(4) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
C5 C6 C7 C8 -178.5(3) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
C1 C2 C7 C6 -177.5(2) . . . . ?
C3 C2 C7 C8 -179.9(3) . . . . ?
C1 C2 C7 C8 1.7(4) . . . . ?
C6 C7 C8 O1 -5.7(4) . . . . ?
C2 C7 C8 O1 175.1(3) . . . . ?
C6 C7 C8 C9 174.3(2) . . . . ?
C2 C7 C8 C9 -4.8(4) . . . . ?
O1 C8 C9 O2 1.5(4) . . . . ?
C7 C8 C9 O2 -178.6(3) . . . . ?
O1 C8 C9 C10 -177.3(3) . . . . ?
C7 C8 C9 C10 2.6(4) . . . . ?
N1 C1 C10 C9 175.9(2) . . . . ?
C2 C1 C10 C9 -6.1(4) . . . . ?
N1 C1 C10 S1 -1.6(3) . . . . ?
C2 C1 C10 S1 176.3(2) . . . . ?
O2 C9 C10 C1 -176.1(3) . . . . ?
C8 C9 C10 C1 2.7(4) . . . . ?
O2 C9 C10 S1 1.3(4) . . . . ?
C8 C9 C10 S1 -179.90(19) . . . . ?
S2 S1 C10 C1 0.9(2) . . . . ?
S2 S1 C10 C9 -176.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.084

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'acetonitrile and chlorobenzene'
####################################################################### 
# 
# 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_chad3
_database_code_depnum_ccdc_archive 'CCDC 1471459'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_chad3               
;
PROBLEM: Short Inter D...A Contact  S1     ..  O3      ..       2.77 Ang.  
RESPONSE:This is expected for this type of structure as it is somewhere 
between an ionic and covalent species. There are electrostatic contacts 
between S(delta positive) and OTf-..
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'4,5-dioxo-naphtho[1,2-d][1,2,3]dithiazol-2-ium triflate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N O2 S2, C F3 O3 S'
_chemical_formula_sum            'C11 H4 F3 N O5 S3'
_chemical_formula_weight         383.33

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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                   17.0537(17)
_cell_length_b                   6.4960(6)
_cell_length_c                   25.224(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2794.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2618
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.78

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8336
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
Alert A, short contacts: This is expected for this type of 
structure as it is somewhere between an ionic and covalent species. 
There are electrostatic contacts between S(delta positive) and OTf- 
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27184
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2462
_reflns_number_gt                1854
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0311P)²+2.3899P] 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         2462
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.12317(4) 0.43491(10) 0.52714(3) 0.02153(18) Uani 1 1 d . . .
S2 S 0.06048(4) 0.66376(10) 0.56053(3) 0.02352(18) Uani 1 1 d . . .
N1 N 0.06150(14) 0.5869(3) 0.62027(9) 0.0237(5) Uani 1 1 d . . .
C1 C 0.09948(16) 0.4104(4) 0.62901(11) 0.0191(6) Uani 1 1 d . . .
C2 C 0.10464(16) 0.3231(4) 0.68287(11) 0.0210(6) Uani 1 1 d . . .
C3 C 0.07415(17) 0.4276(4) 0.72566(11) 0.0297(7) Uani 1 1 d . . .
H3A H 0.0499 0.5578 0.7206 0.036 Uiso 1 1 calc R . .
C4 C 0.0788(2) 0.3439(5) 0.77568(13) 0.0371(8) Uani 1 1 d . . .
H4A H 0.0569 0.4154 0.8050 0.045 Uiso 1 1 calc R . .
C5 C 0.1153(2) 0.1552(5) 0.78341(13) 0.0388(8) Uani 1 1 d . . .
H5A H 0.1187 0.0985 0.8181 0.047 Uiso 1 1 calc R . .
C6 C 0.14658(19) 0.0505(4) 0.74126(12) 0.0312(7) Uani 1 1 d . . .
H6A H 0.1718 -0.0781 0.7468 0.037 Uiso 1 1 calc R . .
C7 C 0.14140(16) 0.1324(4) 0.69028(11) 0.0224(6) Uani 1 1 d . . .
C8 C 0.17641(16) 0.0188(4) 0.64588(11) 0.0227(6) Uani 1 1 d . . .
O1 O 0.20681(12) -0.1499(3) 0.65005(8) 0.0303(5) Uani 1 1 d . . .
C9 C 0.17693(16) 0.1181(4) 0.59005(11) 0.0213(6) Uani 1 1 d . . .
O2 O 0.20956(11) 0.0355(3) 0.55364(8) 0.0276(5) Uani 1 1 d . . .
C10 C 0.13421(15) 0.3161(4) 0.58539(11) 0.0195(6) Uani 1 1 d . . .
O3 O 0.05692(12) 0.6959(3) 0.45276(8) 0.0295(5) Uani 1 1 d . . .
O4 O 0.01019(11) 0.9640(3) 0.39409(7) 0.0266(5) Uani 1 1 d . . .
O5 O 0.08069(12) 1.0536(3) 0.47443(8) 0.0307(5) Uani 1 1 d . . .
S3 S 0.06642(4) 0.90434(10) 0.43390(3) 0.02088(18) Uani 1 1 d . . .
C11 C 0.15906(19) 0.8907(5) 0.39907(13) 0.0362(8) Uani 1 1 d . . .
F1 F 0.17784(12) 1.0726(3) 0.37816(8) 0.0560(6) Uani 1 1 d . . .
F2 F 0.21632(11) 0.8353(3) 0.43148(8) 0.0545(6) Uani 1 1 d . . .
F3 F 0.15634(12) 0.7557(3) 0.35923(8) 0.0601(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0222(4) 0.0188(3) 0.0237(4) 0.0002(3) -0.0016(3) 0.0004(3)
S2 0.0278(4) 0.0164(3) 0.0263(4) -0.0002(3) -0.0040(3) 0.0025(3)
N1 0.0260(14) 0.0196(11) 0.0253(13) -0.0015(10) -0.0039(11) 0.0037(11)
C1 0.0169(15) 0.0160(13) 0.0243(16) -0.0035(11) -0.0028(12) -0.0001(11)
C2 0.0193(15) 0.0199(13) 0.0236(16) -0.0021(12) -0.0017(12) -0.0011(12)
C3 0.0336(19) 0.0300(16) 0.0254(17) -0.0031(14) -0.0007(14) 0.0060(14)
C4 0.043(2) 0.0416(18) 0.0266(18) -0.0056(15) 0.0028(15) 0.0020(16)
C5 0.048(2) 0.0433(18) 0.0252(19) 0.0087(15) -0.0020(16) 0.0005(17)
C6 0.0361(19) 0.0253(15) 0.0321(18) 0.0057(13) -0.0018(15) 0.0020(14)
C7 0.0220(16) 0.0220(14) 0.0233(16) 0.0004(12) -0.0028(13) -0.0038(12)
C8 0.0190(16) 0.0201(15) 0.0289(17) -0.0005(12) -0.0049(13) -0.0022(12)
O1 0.0323(13) 0.0201(10) 0.0386(13) 0.0022(9) -0.0012(10) 0.0068(9)
C9 0.0175(15) 0.0179(14) 0.0285(17) -0.0042(12) -0.0040(13) 0.0001(11)
O2 0.0265(12) 0.0296(11) 0.0267(12) -0.0065(9) -0.0022(9) 0.0079(9)
C10 0.0169(15) 0.0184(13) 0.0231(16) 0.0002(11) -0.0043(12) -0.0039(11)
O3 0.0337(12) 0.0199(10) 0.0348(12) 0.0070(9) -0.0049(10) -0.0021(9)
O4 0.0279(12) 0.0258(10) 0.0261(11) 0.0039(9) -0.0080(9) -0.0020(9)
O5 0.0334(12) 0.0278(11) 0.0308(12) -0.0102(9) -0.0045(10) 0.0040(9)
S3 0.0230(4) 0.0172(3) 0.0224(4) -0.0009(3) -0.0017(3) -0.0001(3)
C11 0.0312(19) 0.0427(19) 0.0348(19) -0.0085(16) 0.0011(16) -0.0039(15)
F1 0.0453(13) 0.0708(14) 0.0520(13) 0.0094(11) 0.0056(10) -0.0300(11)
F2 0.0275(11) 0.0775(15) 0.0586(13) -0.0123(12) -0.0056(10) 0.0162(11)
F3 0.0526(14) 0.0782(15) 0.0495(13) -0.0357(12) 0.0134(11) 0.0005(12)

_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 C10 1.670(3) . ?
S1 S2 2.0155(10) . ?
S2 N1 1.587(2) . ?
N1 C1 1.336(3) . ?
C1 C10 1.391(4) . ?
C1 C2 1.475(4) . ?
C2 C3 1.377(4) . ?
C2 C7 1.401(4) . ?
C3 C4 1.376(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.370(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.394(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.468(4) . ?
C8 O1 1.217(3) . ?
C8 C9 1.549(4) . ?
C9 O2 1.200(3) . ?
C9 C10 1.483(4) . ?
O3 S3 1.4441(19) . ?
O4 S3 1.4416(19) . ?
O5 S3 1.4297(19) . ?
S3 C11 1.810(3) . ?
C11 F2 1.324(4) . ?
C11 F1 1.333(4) . ?
C11 F3 1.335(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 S2 91.90(10) . . ?
N1 S2 S1 99.14(9) . . ?
C1 N1 S2 115.60(19) . . ?
N1 C1 C10 117.0(2) . . ?
N1 C1 C2 120.7(2) . . ?
C10 C1 C2 122.3(2) . . ?
C3 C2 C7 120.0(3) . . ?
C3 C2 C1 120.7(2) . . ?
C7 C2 C1 119.3(2) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 C8 119.1(2) . . ?
C2 C7 C8 121.6(2) . . ?
O1 C8 C7 124.0(3) . . ?
O1 C8 C9 116.8(3) . . ?
C7 C8 C9 119.1(2) . . ?
O2 C9 C10 123.7(3) . . ?
O2 C9 C8 120.8(2) . . ?
C10 C9 C8 115.5(2) . . ?
C1 C10 C9 121.9(2) . . ?
C1 C10 S1 116.4(2) . . ?
C9 C10 S1 121.7(2) . . ?
O5 S3 O4 115.41(11) . . ?
O5 S3 O3 114.79(12) . . ?
O4 S3 O3 114.00(12) . . ?
O5 S3 C11 103.40(14) . . ?
O4 S3 C11 104.81(14) . . ?
O3 S3 C11 102.24(14) . . ?
F2 C11 F1 108.0(3) . . ?
F2 C11 F3 108.2(3) . . ?
F1 C11 F3 107.0(3) . . ?
F2 C11 S3 110.9(2) . . ?
F1 C11 S3 111.0(2) . . ?
F3 C11 S3 111.6(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
C10 S1 S2 N1 0.08(13) . . . . ?
S1 S2 N1 C1 -0.4(2) . . . . ?
S2 N1 C1 C10 0.7(3) . . . . ?
S2 N1 C1 C2 179.9(2) . . . . ?
N1 C1 C2 C3 -3.6(4) . . . . ?
C10 C1 C2 C3 175.6(3) . . . . ?
N1 C1 C2 C7 176.7(2) . . . . ?
C10 C1 C2 C7 -4.1(4) . . . . ?
C7 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C5 C6 C7 C2 0.6(4) . . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
C1 C2 C7 C6 179.7(3) . . . . ?
C3 C2 C7 C8 -178.4(3) . . . . ?
C1 C2 C7 C8 1.2(4) . . . . ?
C6 C7 C8 O1 3.9(4) . . . . ?
C2 C7 C8 O1 -177.7(3) . . . . ?
C6 C7 C8 C9 -174.9(3) . . . . ?
C2 C7 C8 C9 3.6(4) . . . . ?
O1 C8 C9 O2 -3.7(4) . . . . ?
C7 C8 C9 O2 175.1(3) . . . . ?
O1 C8 C9 C10 175.5(2) . . . . ?
C7 C8 C9 C10 -5.6(3) . . . . ?
N1 C1 C10 C9 -179.1(2) . . . . ?
C2 C1 C10 C9 1.7(4) . . . . ?
N1 C1 C10 S1 -0.6(3) . . . . ?
C2 C1 C10 S1 -179.8(2) . . . . ?
O2 C9 C10 C1 -177.7(3) . . . . ?
C8 C9 C10 C1 3.1(4) . . . . ?
O2 C9 C10 S1 3.9(4) . . . . ?
C8 C9 C10 S1 -175.30(19) . . . . ?
S2 S1 C10 C1 0.3(2) . . . . ?
S2 S1 C10 C9 178.7(2) . . . . ?
O5 S3 C11 F2 59.2(2) . . . . ?
O4 S3 C11 F2 -179.5(2) . . . . ?
O3 S3 C11 F2 -60.3(2) . . . . ?
O5 S3 C11 F1 -60.9(2) . . . . ?
O4 S3 C11 F1 60.4(2) . . . . ?
O3 S3 C11 F1 179.6(2) . . . . ?
O5 S3 C11 F3 179.9(2) . . . . ?
O4 S3 C11 F3 -58.9(3) . . . . ?
O3 S3 C11 F3 60.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.063



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'acetonitrile and toluene'
####################################################################### 
# 
# 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_kp110944
_database_code_depnum_ccdc_archive 'CCDC 1471460'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_kp110944            
;
PROBLEM: Short Inter D...A Contact  S2     ..  O1      ..       2.76 Ang.  
RESPONSE:This is expected for this type of structure as it is somewhere 
between an ionic and covalent species. There are electrostatic contacts 1
between S(delta positive) and O(delta negative)
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'5-oxo-naphtho[1,2-d][1,2,3]dithiazol-4-yl acetate'
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H7 N O3 S2'
_chemical_formula_sum            'C12 H7 N O3 S2'
_exptl_crystal_recrystallization_method Sublimation
_chemical_melting_point          ?

_exptl_crystal_description       Rod
_exptl_crystal_colour            Orange

_diffrn_ambient_temperature      198(1)
_chemical_formula_weight         277.31

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

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

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                   4.7207(5)
_cell_length_b                   13.3232(13)
_cell_length_c                   18.4301(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.977(2)
_cell_angle_gamma                90.00
_cell_volume                     1157.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    198(1)
_cell_measurement_reflns_used    4136
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      28.20
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9141
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
Alert A/B, short contacts: This is expected for this type of 
structure as it is somewhere between an ionic and covalent species. 
There are electrostatic contacts between S(delta positive and 
O(delta negative.
Crystal decay was monitored by repeating the initial 50 frames
at the end of the data collection and analyzing duplicate
reflections.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8030
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2604
_reflns_number_gt                1978
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.3227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2604
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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 0.12090(11) -0.04718(3) 0.76646(3) 0.03158(14) Uani 1 1 d . . .
S2 S 0.22982(11) -0.11585(4) 0.86550(3) 0.03558(15) Uani 1 1 d . . .
N1 N 0.4688(3) -0.03604(12) 0.89509(9) 0.0324(4) Uani 1 1 d . . .
C9 C 0.4204(4) 0.12255(14) 0.73577(10) 0.0298(4) Uani 1 1 d . . .
C10 C 0.3691(4) 0.04694(13) 0.78283(10) 0.0273(4) Uani 1 1 d . . .
C1 C 0.5231(4) 0.03947(13) 0.85281(10) 0.0280(4) Uani 1 1 d . . .
C2 C 0.7333(4) 0.11608(13) 0.87367(10) 0.0280(4) Uani 1 1 d . . .
C7 C 0.7806(4) 0.19429(14) 0.82477(10) 0.0295(4) Uani 1 1 d . . .
C8 C 0.6272(4) 0.19996(14) 0.75256(10) 0.0306(4) Uani 1 1 d . . .
C3 C 0.8838(4) 0.11328(15) 0.94065(11) 0.0334(4) Uani 1 1 d . . .
C4 C 1.0826(5) 0.18629(17) 0.95849(12) 0.0397(5) Uani 1 1 d . . .
C5 C 1.1291(5) 0.26398(17) 0.91011(13) 0.0422(5) Uani 1 1 d . . .
C6 C 0.9795(5) 0.26844(15) 0.84439(12) 0.0363(5) Uani 1 1 d . . .
C11 C 0.3647(5) 0.08739(16) 0.61127(11) 0.0380(5) Uani 1 1 d . . .
C12 C 0.1848(7) 0.1126(2) 0.54510(14) 0.0522(6) Uani 1 1 d . . .
O2 O 0.2576(3) 0.13062(10) 0.67091(7) 0.0364(3) Uani 1 1 d . . .
O1 O 0.6719(3) 0.26838(10) 0.70926(8) 0.0400(4) Uani 1 1 d . . .
O3 O 0.5726(4) 0.03685(15) 0.61471(9) 0.0616(5) Uani 1 1 d . . .
H3A H 0.850(4) 0.0587(16) 0.9744(12) 0.038(6) Uiso 1 1 d . . .
H4A H 1.185(5) 0.1810(18) 1.0030(13) 0.054(7) Uiso 1 1 d . . .
H5A H 1.257(5) 0.3150(18) 0.9228(12) 0.053(7) Uiso 1 1 d . . .
H6A H 1.002(4) 0.3211(16) 0.8116(12) 0.041(6) Uiso 1 1 d . . .
H12A H 0.179(7) 0.185(3) 0.5391(18) 0.097(11) Uiso 1 1 d . . .
H12B H 0.247(6) 0.080(2) 0.5044(16) 0.070(9) Uiso 1 1 d . . .
H12C H -0.009(6) 0.089(2) 0.5512(14) 0.069(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0343(3) 0.0295(2) 0.0312(3) -0.00445(19) 0.0040(2) 0.0008(2)
S2 0.0431(3) 0.0289(3) 0.0350(3) 0.00193(19) 0.0043(2) -0.0044(2)
N1 0.0370(10) 0.0283(8) 0.0321(9) 0.0022(7) 0.0042(7) -0.0004(7)
C9 0.0309(10) 0.0316(10) 0.0273(10) 0.0008(8) 0.0039(8) 0.0080(8)
C10 0.0281(10) 0.0252(9) 0.0292(9) -0.0033(7) 0.0070(8) 0.0043(7)
C1 0.0288(10) 0.0263(9) 0.0293(10) -0.0013(7) 0.0067(8) 0.0056(8)
C2 0.0275(10) 0.0253(9) 0.0318(10) -0.0022(7) 0.0077(8) 0.0058(8)
C7 0.0272(10) 0.0273(9) 0.0348(10) -0.0014(8) 0.0086(8) 0.0064(8)
C8 0.0294(10) 0.0281(10) 0.0351(10) 0.0030(8) 0.0099(8) 0.0083(8)
C3 0.0339(11) 0.0331(10) 0.0334(10) 0.0008(8) 0.0046(9) 0.0028(8)
C4 0.0372(12) 0.0443(12) 0.0373(12) -0.0054(9) -0.0007(10) 0.0027(10)
C5 0.0374(13) 0.0423(12) 0.0472(13) -0.0075(10) 0.0051(10) -0.0080(10)
C6 0.0360(12) 0.0309(10) 0.0430(12) 0.0021(9) 0.0114(10) -0.0018(9)
C11 0.0427(13) 0.0381(11) 0.0337(11) 0.0006(9) 0.0062(10) -0.0071(10)
C12 0.0611(18) 0.0601(17) 0.0351(13) 0.0015(12) -0.0006(12) -0.0145(14)
O2 0.0389(8) 0.0407(8) 0.0296(7) 0.0027(6) 0.0005(6) 0.0084(6)
O1 0.0410(9) 0.0364(8) 0.0430(9) 0.0132(6) 0.0068(7) 0.0033(6)
O3 0.0599(11) 0.0799(13) 0.0455(10) -0.0140(9) 0.0082(8) 0.0210(10)

_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 C10 1.7319(19) . ?
S1 S2 2.0824(7) . ?
S2 N1 1.6240(17) . ?
N1 C1 1.306(2) . ?
C9 C10 1.359(3) . ?
C9 O2 1.391(2) . ?
C9 C8 1.443(3) . ?
C10 C1 1.451(3) . ?
C1 C2 1.461(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.403(3) . ?
C7 C6 1.398(3) . ?
C7 C8 1.484(3) . ?
C8 O1 1.237(2) . ?
C3 C4 1.380(3) . ?
C3 H3A 0.98(2) . ?
C4 C5 1.391(3) . ?
C4 H4A 0.93(2) . ?
C5 C6 1.371(3) . ?
C5 H5A 0.93(2) . ?
C6 H6A 0.94(2) . ?
C11 O3 1.189(3) . ?
C11 O2 1.361(2) . ?
C11 C12 1.488(3) . ?
C12 H12A 0.97(3) . ?
C12 H12B 0.93(3) . ?
C12 H12C 0.98(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 S2 91.80(7) . . ?
N1 S2 S1 98.18(6) . . ?
C1 N1 S2 117.29(14) . . ?
C10 C9 O2 119.79(18) . . ?
C10 C9 C8 122.27(17) . . ?
O2 C9 C8 117.81(16) . . ?
C9 C10 C1 121.36(17) . . ?
C9 C10 S1 124.52(15) . . ?
C1 C10 S1 114.11(13) . . ?
N1 C1 C10 118.59(17) . . ?
N1 C1 C2 122.19(17) . . ?
C10 C1 C2 119.22(16) . . ?
C3 C2 C7 119.90(18) . . ?
C3 C2 C1 121.52(17) . . ?
C7 C2 C1 118.58(17) . . ?
C6 C7 C2 119.08(18) . . ?
C6 C7 C8 119.09(18) . . ?
C2 C7 C8 121.83(17) . . ?
O1 C8 C9 121.65(18) . . ?
O1 C8 C7 121.64(18) . . ?
C9 C8 C7 116.71(16) . . ?
C4 C3 C2 120.13(19) . . ?
C4 C3 H3A 120.4(13) . . ?
C2 C3 H3A 119.5(13) . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4A 118.2(15) . . ?
C5 C4 H4A 121.8(15) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5A 119.1(15) . . ?
C4 C5 H5A 120.3(15) . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6A 122.2(14) . . ?
C7 C6 H6A 117.4(13) . . ?
O3 C11 O2 122.5(2) . . ?
O3 C11 C12 127.3(2) . . ?
O2 C11 C12 110.2(2) . . ?
C11 C12 H12A 109.2(19) . . ?
C11 C12 H12B 111.5(18) . . ?
H12A C12 H12B 113(3) . . ?
C11 C12 H12C 109.3(16) . . ?
H12A C12 H12C 108(3) . . ?
H12B C12 H12C 106(2) . . ?
C11 O2 C9 116.70(16) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1471642'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_twin5               
;
PROBLEM: Short Inter D...A Contact  S2B    ..  O2A     ..       2.77 Ang.  
RESPONSE:This is expected for this type of structure as it is somewhere 
between an ionic and covalent species. There are electrostatic contacts 
between S(delta positive) and O(delta negative).
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        naphtha[1,2-d][1,2,3]dithiazolyl-4,5-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N O2 S2'
_chemical_formula_sum            'C10 H4 N O2 S2'
_chemical_formula_weight         234.26

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.3156(16)
_cell_length_b                   10.872(2)
_cell_length_c                   10.992(2)
_cell_angle_alpha                61.995(3)
_cell_angle_beta                 86.869(4)
_cell_angle_gamma                85.509(4)
_cell_volume                     874.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    647
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.26

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.579

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8454
_exptl_absorpt_correction_T_max  0.8930
_exptl_absorpt_process_details   TWINABS

_exptl_special_details           
;
Alert A/B, short contacts: This is expected for this type of 
structure as it is somewhere between an ionic and covalent species. 
There are electrostatic contacts between S(delta positive) 
and O(delta negative).
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6444
_diffrn_reflns_av_R_equivalents  0.1313
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         30.03
_reflns_number_total             5005
_reflns_number_gt                4140
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2σ(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)+(0.0440P)²+0.2973P] 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         5250
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C8b C 1.8373(2) 0.69652(17) 0.98485(17) 0.0181(3) Uani 1 1 d . . .
C8a C 1.3438(2) 0.27847(19) 0.69938(18) 0.0215(3) Uani 1 1 d . . .
C3a C 1.1642(2) -0.01443(17) 0.66523(18) 0.0205(3) Uani 1 1 d . . .
H3aA H 1.1013 -0.0273 0.6051 0.025 Uiso 1 1 calc R . .
C5a C 1.3174(2) -0.1109(2) 0.87410(19) 0.0275(4) Uani 1 1 d . . .
H5aA H 1.3546 -0.1880 0.9538 0.033 Uiso 1 1 calc R . .
S2a S 0.98913(5) 0.37572(4) 0.29348(4) 0.01998(10) Uani 1 1 d . . .
S1a S 1.10298(5) 0.51262(4) 0.33611(4) 0.02004(9) Uani 1 1 d . . .
S2b S 1.48415(5) 0.67922(4) 0.62665(5) 0.02097(10) Uani 1 1 d . . .
S1b S 1.57466(5) 0.51824(4) 0.80769(5) 0.02088(10) Uani 1 1 d . . .
C10b C 1.6689(2) 0.63437(16) 0.84046(17) 0.0172(3) Uani 1 1 d . . .
C7a C 1.2989(2) 0.13784(18) 0.72678(17) 0.0190(3) Uani 1 1 d . . .
C10a C 1.1803(2) 0.37739(16) 0.48496(17) 0.0171(3) Uani 1 1 d . . .
O2b O 1.78884(17) 0.45967(13) 1.04250(13) 0.0277(3) Uani 1 1 d . . .
C7b C 1.8051(2) 0.84524(17) 0.88322(17) 0.0166(3) Uani 1 1 d . . .
N1a N 1.04385(18) 0.23029(14) 0.42770(14) 0.0180(3) Uani 1 1 d . . .
O2a O 1.31454(17) 0.52372(13) 0.54339(15) 0.0291(3) Uani 1 1 d . . .
C1b C 1.64618(19) 0.77647(16) 0.74266(17) 0.0161(3) Uani 1 1 d . . .
C2b C 1.71795(19) 0.88403(16) 0.76234(16) 0.0155(3) Uani 1 1 d . . .
O1a O 1.42814(19) 0.29573(16) 0.77628(16) 0.0351(3) Uani 1 1 d . . .
O1b O 1.91645(17) 0.66103(13) 1.08739(14) 0.0271(3) Uani 1 1 d . . .
C1a C 1.13823(19) 0.24231(16) 0.51456(16) 0.0161(3) Uani 1 1 d . . .
C3b C 1.6968(2) 1.02490(17) 0.66655(17) 0.0190(3) Uani 1 1 d . . .
H3bA H 1.6427 1.0508 0.5855 0.023 Uiso 1 1 calc R . .
C9b C 1.7660(2) 0.58405(17) 0.96050(17) 0.0185(3) Uani 1 1 d . . .
C6a C 1.3564(2) 0.0216(2) 0.84502(18) 0.0260(4) Uani 1 1 d . . .
H6aA H 1.4213 0.0332 0.9046 0.031 Uiso 1 1 calc R . .
N1b N 1.55785(17) 0.80997(14) 0.63344(15) 0.0188(3) Uani 1 1 d . . .
C9a C 1.2811(2) 0.40546(18) 0.56928(18) 0.0201(3) Uani 1 1 d . . .
C6b C 1.8626(2) 0.94851(18) 0.90686(18) 0.0213(3) Uani 1 1 d . . .
H6bA H 1.9187 0.9237 0.9868 0.026 Uiso 1 1 calc R . .
C2a C 1.2008(2) 0.11957(16) 0.63692(16) 0.0166(3) Uani 1 1 d . . .
C4b C 1.7560(2) 1.12650(17) 0.69149(18) 0.0210(3) Uani 1 1 d . . .
H4bA H 1.7414 1.2202 0.6274 0.025 Uiso 1 1 calc R . .
C4a C 1.2222(2) -0.12828(19) 0.7836(2) 0.0262(4) Uani 1 1 d . . .
H4aA H 1.1972 -0.2176 0.8028 0.031 Uiso 1 1 calc R . .
C5b C 1.8374(2) 1.08783(17) 0.81282(19) 0.0221(3) Uani 1 1 d . . .
H5bA H 1.8749 1.1561 0.8306 0.027 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C8b 0.0203(8) 0.0159(7) 0.0159(7) -0.0054(6) -0.0016(6) -0.0006(6)
C8a 0.0213(8) 0.0251(8) 0.0216(8) -0.0135(7) -0.0013(6) -0.0032(7)
C3a 0.0243(8) 0.0151(7) 0.0199(8) -0.0061(6) 0.0000(6) -0.0032(6)
C5a 0.0291(9) 0.0244(9) 0.0184(8) -0.0023(7) -0.0012(7) 0.0058(8)
S2a 0.0209(2) 0.0185(2) 0.01774(19) -0.00585(16) -0.00487(15) -0.00036(15)
S1a 0.0247(2) 0.01227(18) 0.0203(2) -0.00546(16) -0.00134(16) 0.00061(15)
S2b 0.02013(19) 0.0212(2) 0.0253(2) -0.01332(18) -0.00492(16) -0.00255(16)
S1b 0.0242(2) 0.01619(19) 0.0227(2) -0.00879(16) 0.00168(16) -0.00713(16)
C10b 0.0195(7) 0.0136(7) 0.0186(7) -0.0071(6) -0.0004(6) -0.0038(6)
C7a 0.0189(7) 0.0215(8) 0.0170(7) -0.0092(7) -0.0010(6) -0.0017(6)
C10a 0.0189(7) 0.0131(7) 0.0183(7) -0.0064(6) -0.0007(6) -0.0010(6)
O2b 0.0391(8) 0.0144(6) 0.0223(6) -0.0018(5) -0.0058(6) -0.0029(5)
C7b 0.0181(7) 0.0153(7) 0.0152(7) -0.0060(6) -0.0025(6) 0.0001(6)
N1a 0.0198(7) 0.0160(6) 0.0172(7) -0.0064(5) -0.0026(5) -0.0035(5)
O2a 0.0317(7) 0.0210(7) 0.0409(8) -0.0189(6) 0.0001(6) -0.0078(5)
C1b 0.0156(7) 0.0149(7) 0.0184(7) -0.0081(6) -0.0019(6) -0.0006(6)
C2b 0.0177(7) 0.0132(7) 0.0167(7) -0.0077(6) -0.0022(6) 0.0000(6)
O1a 0.0374(8) 0.0400(8) 0.0367(8) -0.0235(7) -0.0125(6) -0.0071(7)
O1b 0.0349(7) 0.0195(6) 0.0223(6) -0.0054(5) -0.0122(5) 0.0016(5)
C1a 0.0172(7) 0.0148(7) 0.0166(7) -0.0074(6) -0.0005(6) -0.0027(6)
C3b 0.0226(8) 0.0151(7) 0.0180(8) -0.0065(6) -0.0048(6) 0.0008(6)
C9b 0.0209(8) 0.0147(7) 0.0165(7) -0.0044(6) -0.0007(6) -0.0023(6)
C6a 0.0268(9) 0.0306(10) 0.0174(8) -0.0087(7) -0.0051(7) 0.0024(8)
N1b 0.0190(7) 0.0173(7) 0.0219(7) -0.0105(6) -0.0046(5) 0.0004(5)
C9a 0.0194(7) 0.0202(8) 0.0249(8) -0.0139(7) 0.0008(6) -0.0035(6)
C6b 0.0255(8) 0.0198(8) 0.0202(8) -0.0099(7) -0.0051(6) -0.0031(7)
C2a 0.0186(7) 0.0148(7) 0.0148(7) -0.0053(6) -0.0004(6) -0.0025(6)
C4b 0.0253(8) 0.0129(7) 0.0229(8) -0.0067(7) -0.0030(7) -0.0002(6)
C4a 0.0301(9) 0.0147(8) 0.0259(9) -0.0033(7) 0.0049(7) -0.0021(7)
C5b 0.0264(8) 0.0164(8) 0.0248(8) -0.0102(7) -0.0034(7) -0.0027(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C8b O1b 1.2186(19) . ?
C8b C7b 1.484(2) . ?
C8b C9b 1.535(2) . ?
C8a O1a 1.215(2) . ?
C8a C7a 1.487(2) . ?
C8a C9a 1.529(2) . ?
C3a C4a 1.385(2) . ?
C3a C2a 1.395(2) . ?
C5a C6a 1.382(3) . ?
C5a C4a 1.393(3) . ?
S2a N1a 1.6290(14) . ?
S2a S1a 2.0628(6) . ?
S1a C10a 1.7204(16) . ?
S2b N1b 1.6257(14) . ?
S2b S1b 2.0680(7) . ?
S1b C10b 1.7177(16) . ?
C10b C1b 1.412(2) . ?
C10b C9b 1.436(2) . ?
C7a C6a 1.395(2) . ?
C7a C2a 1.407(2) . ?
C10a C1a 1.416(2) . ?
C10a C9a 1.430(2) . ?
O2b C9b 1.229(2) . ?
C7b C6b 1.389(2) . ?
C7b C2b 1.414(2) . ?
N1a C1a 1.3265(19) . ?
O2a C9a 1.2310(19) . ?
C1b N1b 1.3256(19) . ?
C1b C2b 1.460(2) . ?
C2b C3b 1.396(2) . ?
C1a C2a 1.464(2) . ?
C3b C4b 1.386(2) . ?
C6b C5b 1.382(2) . ?
C4b C5b 1.393(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
O1b C8b C7b 122.30(15) . . ?
O1b C8b C9b 119.11(15) . . ?
C7b C8b C9b 118.59(13) . . ?
O1a C8a C7a 122.45(17) . . ?
O1a C8a C9a 119.14(16) . . ?
C7a C8a C9a 118.41(14) . . ?
C4a C3a C2a 119.51(16) . . ?
C6a C5a C4a 119.70(16) . . ?
N1a S2a S1a 98.98(5) . . ?
C10a S1a S2a 91.19(6) . . ?
N1b S2b S1b 99.27(5) . . ?
C10b S1b S2b 90.77(6) . . ?
C1b C10b C9b 124.14(14) . . ?
C1b C10b S1b 116.06(12) . . ?
C9b C10b S1b 119.79(12) . . ?
C6a C7a C2a 119.56(15) . . ?
C6a C7a C8a 118.66(15) . . ?
C2a C7a C8a 121.78(15) . . ?
C1a C10a C9a 124.26(15) . . ?
C1a C10a S1a 115.81(12) . . ?
C9a C10a S1a 119.92(12) . . ?
C6b C7b C2b 119.27(15) . . ?
C6b C7b C8b 119.33(14) . . ?
C2b C7b C8b 121.40(14) . . ?
C1a N1a S2a 115.64(11) . . ?
N1b C1b C10b 118.68(14) . . ?
N1b C1b C2b 120.85(14) . . ?
C10b C1b C2b 120.47(14) . . ?
C3b C2b C7b 119.43(14) . . ?
C3b C2b C1b 121.17(14) . . ?
C7b C2b C1b 119.36(14) . . ?
N1a C1a C10a 118.37(14) . . ?
N1a C1a C2a 121.36(14) . . ?
C10a C1a C2a 120.26(13) . . ?
C4b C3b C2b 120.45(15) . . ?
O2b C9b C10b 123.46(15) . . ?
O2b C9b C8b 120.74(15) . . ?
C10b C9b C8b 115.77(14) . . ?
C5a C6a C7a 120.40(16) . . ?
C1b N1b S2b 115.21(12) . . ?
O2a C9a C10a 123.54(16) . . ?
O2a C9a C8a 120.42(15) . . ?
C10a C9a C8a 116.02(14) . . ?
C5b C6b C7b 120.70(15) . . ?
C3a C2a C7a 119.88(15) . . ?
C3a C2a C1a 120.89(14) . . ?
C7a C2a C1a 119.23(14) . . ?
C3b C4b C5b 119.81(15) . . ?
C3a C4a C5a 120.93(17) . . ?
C6b C5b C4b 120.29(15) . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        30.66
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.076


















_exptl_crystal_recrystallization_method Sublimation
