# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof Edward R.T. Tiekink'
_publ_contact_author_email       EDWARD.TIEKINK@UTSA.EDU

_publ_section_title              
;
The influence of cation upon the supramolecular
aggregation patterns of dithiocarbamate anions functionalised with
hydrogen bonding capacity - the prevalence of charge-assisted O-H...S
interactions
;
loop_
_publ_author_name
'Edward R.T. Tiekink'
'Geraldo de Lima'
'R A Howie'
'Daniela C. Menezes'
'James L. Wardell'
;
S.M.S.V.Wardell
;
'David J. Young'

# Attachment '1.CIF'

data_1
_database_code_depnum_ccdc_archive 'CCDC 690732'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 N O2 S2, H4 N'
_chemical_formula_sum            'C5 H14 N2 O2 S2'
_chemical_formula_weight         198.30

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

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   14.0102(15)
_cell_length_b                   8.0880(9)
_cell_length_c                   15.8727(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1798.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5687
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            39454
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.012
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.5
_diffrn_reflns_theta_max         26.5
_reflns_number_total             1838
_reflns_number_gt                1799
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97

_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)+(0.0336P)²+0.9098P] 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         1838
_refine_ls_number_parameters     118
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.028
_refine_ls_wR_factor_ref         0.068
_refine_ls_wR_factor_gt          0.067
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_restrained_S_all      1.12
_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 -0.05826(2) 0.65947(4) 0.43744(2) 0.01806(11) Uani 1 1 d . . .
S2 S -0.16057(2) 0.73554(4) 0.27853(2) 0.01750(11) Uani 1 1 d . . .
O1 O 0.25724(7) 0.78248(13) 0.41003(6) 0.0209(2) Uani 1 1 d D . .
H1O H 0.2970 0.7669 0.3712 0.031 Uiso 1 1 d D . .
O2 O 0.09359(7) 0.68934(13) 0.06772(6) 0.0204(2) Uani 1 1 d D . .
H2O H 0.0553 0.7308 0.0329 0.031 Uiso 1 1 d D . .
N1 N 0.02937(8) 0.72405(13) 0.29226(7) 0.0135(2) Uani 1 1 d . . .
N2 N 0.25872(8) 0.55460(14) 0.55380(7) 0.0174(2) Uani 1 1 d D . .
H1N H 0.2696 0.6149 0.5989 0.026 Uiso 1 1 d D . .
H2N H 0.3047 0.4810 0.5494 0.026 Uiso 1 1 d D . .
H3N H 0.2593 0.6202 0.5096 0.026 Uiso 1 1 d D . .
H4N H 0.2032 0.5042 0.5576 0.026 Uiso 1 1 d D . .
C1 C -0.05480(9) 0.70938(15) 0.33232(8) 0.0138(3) Uani 1 1 d . . .
C2 C 0.12033(9) 0.67945(16) 0.33261(8) 0.0155(3) Uani 1 1 d . . .
H2A H 0.1627 0.6270 0.2905 0.019 Uiso 1 1 calc R . .
H2B H 0.1082 0.5980 0.3779 0.019 Uiso 1 1 calc R . .
C3 C 0.16995(9) 0.83012(17) 0.36973(8) 0.0163(3) Uani 1 1 d . . .
H3A H 0.1837 0.9108 0.3244 0.020 Uiso 1 1 calc R . .
H3B H 0.1274 0.8840 0.4113 0.020 Uiso 1 1 calc R . .
C4 C 0.03899(10) 0.78463(16) 0.20537(8) 0.0155(3) Uani 1 1 d . . .
H4A H 0.0984 0.8502 0.2005 0.019 Uiso 1 1 calc R . .
H4B H -0.0154 0.8584 0.1922 0.019 Uiso 1 1 calc R . .
C5 C 0.04161(11) 0.64363(17) 0.14159(9) 0.0197(3) Uani 1 1 d . . .
H5A H 0.0719 0.5456 0.1677 0.024 Uiso 1 1 calc R . .
H5B H -0.0244 0.6133 0.1257 0.024 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
S1 0.0157(2) 0.0262(2) 0.01227(18) 0.00248(12) -0.00033(11) -0.00421(13)
S2 0.01284(19) 0.02425(19) 0.01541(18) -0.00264(12) -0.00286(12) 0.00180(12)
O1 0.0146(5) 0.0321(6) 0.0159(5) 0.0016(4) -0.0031(4) -0.0010(4)
O2 0.0205(6) 0.0279(5) 0.0129(5) 0.0031(4) 0.0017(4) 0.0072(4)
N1 0.0118(5) 0.0161(5) 0.0127(5) 0.0009(4) -0.0007(4) -0.0001(4)
N2 0.0146(6) 0.0181(6) 0.0193(6) -0.0006(4) -0.0004(5) -0.0003(4)
C1 0.0155(7) 0.0118(6) 0.0141(6) -0.0018(5) -0.0012(5) -0.0003(5)
C2 0.0122(6) 0.0180(6) 0.0163(6) 0.0003(5) -0.0011(5) 0.0012(5)
C3 0.0141(7) 0.0206(7) 0.0143(6) 0.0005(5) -0.0013(5) -0.0001(5)
C4 0.0182(7) 0.0158(6) 0.0124(6) 0.0016(5) 0.0013(5) -0.0012(5)
C5 0.0244(7) 0.0192(7) 0.0154(6) -0.0010(5) 0.0040(5) -0.0011(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7174(14) . ?
S2 C1 1.7232(14) . ?
O1 C3 1.4330(16) . ?
O1 H1O 0.84000 . ?
O2 C5 1.4289(17) . ?
O2 H2O 0.84000 . ?
N1 C1 1.3450(17) . ?
N1 C4 1.4698(17) . ?
N1 C2 1.4711(17) . ?
N2 H1N 0.88000 . ?
N2 H2N 0.88000 . ?
N2 H3N 0.88000 . ?
N2 H4N 0.88000 . ?
C2 C3 1.5216(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5253(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
C3 O1 H1O 106.1 . . ?
C5 O2 H2O 108.5 . . ?
C1 N1 C4 123.60(11) . . ?
C1 N1 C2 122.15(11) . . ?
C4 N1 C2 114.25(11) . . ?
H1N N2 H2N 108.3 . . ?
H1N N2 H3N 108.3 . . ?
H2N N2 H3N 109.7 . . ?
H1N N2 H4N 110.7 . . ?
H2N N2 H4N 109.8 . . ?
H3N N2 H4N 110.0 . . ?
N1 C1 S1 120.31(10) . . ?
N1 C1 S2 120.60(10) . . ?
S1 C1 S2 119.08(8) . . ?
N1 C2 C3 111.59(10) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C2 110.33(11) . . ?
O1 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
O1 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C5 112.07(10) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 C4 111.31(11) . . ?
O2 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
O2 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?

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
C4 N1 C1 S1 -172.74(9) . . . . ?
C2 N1 C1 S1 7.46(16) . . . . ?
C4 N1 C1 S2 8.78(17) . . . . ?
C2 N1 C1 S2 -171.01(9) . . . . ?
C1 N1 C2 C3 -96.74(14) . . . . ?
C4 N1 C2 C3 83.44(13) . . . . ?
N1 C2 C3 O1 178.83(10) . . . . ?
C1 N1 C4 C5 -94.53(15) . . . . ?
C2 N1 C4 C5 85.28(14) . . . . ?
N1 C4 C5 O2 -152.59(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.5
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.049

# Attachment '2.CIF'

data_2
_database_code_depnum_ccdc_archive 'CCDC 690733'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-aza-1-azoniabicyclo(2.2.2)octanium bis(ethanol)dithiocarbamate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H13 N2, C5 H10 N O2 S2'
_chemical_formula_sum            'C11 H23 N3 O2 S2'
_chemical_formula_weight         293.44

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

_symmetry_cell_setting           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                   7.7299(3)
_cell_length_b                   9.8682(4)
_cell_length_c                   10.1834(4)
_cell_angle_alpha                70.968(2)
_cell_angle_beta                 81.797(2)
_cell_angle_gamma                75.6620(18)
_cell_volume                     709.83(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3079
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       slab
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_type   multi-scan
# compare SADABS Tmin/max (below) with calc 0.8349/0.9707
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
;
Unit cell determined with DirAx (Duisenberg, 1992; Duisenberg et al. 2000)
but refined with the DENZO/COLLECT HKL package.

Refs as:
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J.
(2000). J. Appl. Cryst. 33, 893-898.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            12002
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.7
_diffrn_reflns_theta_max         27.6
_reflns_number_total             3251
_reflns_number_gt                2557
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97

_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)+(0.0336P)²+0.3389P] 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         3251
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.034
_refine_ls_wR_factor_ref         0.083
_refine_ls_wR_factor_gt          0.076
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_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 0.81602(6) 0.21037(5) 0.45911(4) 0.02267(12) Uani 1 1 d . . .
S2 S 0.55152(5) 0.40285(5) 0.25289(4) 0.01912(11) Uani 1 1 d . . .
O1 O 1.36194(15) 0.16581(12) 0.22330(13) 0.0236(3) Uani 1 1 d . . .
H1O H 1.4362 0.2117 0.2309 0.035 Uiso 1 1 calc R . .
O2 O 0.85040(16) 0.12687(12) -0.03340(12) 0.0219(3) Uani 1 1 d . . .
H2O H 0.9481 0.1345 -0.0803 0.033 Uiso 1 1 calc R . .
N1 N 0.87721(17) 0.26504(14) 0.18500(13) 0.0143(3) Uani 1 1 d . . .
N2 N 0.41867(18) 0.24538(14) 0.60033(14) 0.0169(3) Uani 1 1 d . . .
H2N H 0.5127 0.2597 0.5329 0.020 Uiso 1 1 calc R . .
N3 N 0.16333(18) 0.20607(15) 0.78461(14) 0.0191(3) Uani 1 1 d . . .
C1 C 0.7594(2) 0.28970(16) 0.29024(16) 0.0150(3) Uani 1 1 d . . .
C2 C 1.0571(2) 0.17022(17) 0.20985(16) 0.0157(3) Uani 1 1 d . . .
H2A H 1.0946 0.1201 0.1373 0.019 Uiso 1 1 calc R . .
H2B H 1.0540 0.0942 0.3015 0.019 Uiso 1 1 calc R . .
C3 C 1.1900(2) 0.26067(18) 0.20682(18) 0.0184(3) Uani 1 1 d . . .
H3A H 1.1896 0.3400 0.1172 0.022 Uiso 1 1 calc R . .
H3B H 1.1579 0.3059 0.2831 0.022 Uiso 1 1 calc R . .
C4 C 0.8422(2) 0.34385(17) 0.03841(16) 0.0176(3) Uani 1 1 d . . .
H4A H 0.9574 0.3585 -0.0145 0.021 Uiso 1 1 calc R . .
H4B H 0.7662 0.4421 0.0327 0.021 Uiso 1 1 calc R . .
C5 C 0.7517(2) 0.26799(18) -0.03128(17) 0.0201(4) Uani 1 1 d . . .
H5A H 0.6332 0.2585 0.0180 0.024 Uiso 1 1 calc R . .
H5B H 0.7314 0.3306 -0.1283 0.024 Uiso 1 1 calc R . .
C6 C 0.4873(2) 0.20858(19) 0.74106(17) 0.0207(4) Uani 1 1 d . . .
H6A H 0.5352 0.2905 0.7469 0.025 Uiso 1 1 calc R . .
H6B H 0.5847 0.1194 0.7576 0.025 Uiso 1 1 calc R . .
C7 C 0.3301(2) 0.1822(2) 0.85030(18) 0.0273(4) Uani 1 1 d . . .
H7A H 0.3581 0.0802 0.9132 0.033 Uiso 1 1 calc R . .
H7B H 0.3137 0.2495 0.9071 0.033 Uiso 1 1 calc R . .
C8 C 0.1256(3) 0.35645(19) 0.6883(2) 0.0300(4) Uani 1 1 d . . .
H8A H 0.1114 0.4273 0.7411 0.036 Uiso 1 1 calc R . .
H8B H 0.0116 0.3741 0.6456 0.036 Uiso 1 1 calc R . .
C9 C 0.2761(2) 0.38226(17) 0.57288(17) 0.0202(4) Uani 1 1 d . . .
H9A H 0.2296 0.4051 0.4807 0.024 Uiso 1 1 calc R . .
H9B H 0.3249 0.4658 0.5735 0.024 Uiso 1 1 calc R . .
C10 C 0.3466(2) 0.12062(18) 0.59321(17) 0.0199(4) Uani 1 1 d . . .
H10A H 0.4407 0.0293 0.6124 0.024 Uiso 1 1 calc R . .
H10B H 0.3058 0.1419 0.4993 0.024 Uiso 1 1 calc R . .
C11 C 0.1884(2) 0.10269(18) 0.70367(17) 0.0217(4) Uani 1 1 d . . .
H11A H 0.0776 0.1195 0.6570 0.026 Uiso 1 1 calc R . .
H11B H 0.2105 0.0010 0.7675 0.026 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
S1 0.0186(2) 0.0302(2) 0.0152(2) -0.00509(17) -0.00116(16) -0.00032(18)
S2 0.0149(2) 0.0188(2) 0.0243(2) -0.00884(17) -0.00320(16) -0.00046(16)
O1 0.0130(6) 0.0206(6) 0.0376(7) -0.0085(5) -0.0035(5) -0.0037(5)
O2 0.0224(7) 0.0214(6) 0.0228(6) -0.0089(5) 0.0012(5) -0.0050(5)
N1 0.0134(7) 0.0145(6) 0.0145(6) -0.0035(5) -0.0019(5) -0.0029(5)
N2 0.0168(7) 0.0179(7) 0.0159(7) -0.0060(5) 0.0021(5) -0.0041(6)
N3 0.0188(7) 0.0190(7) 0.0197(7) -0.0066(6) 0.0010(6) -0.0050(6)
C1 0.0145(8) 0.0140(7) 0.0194(8) -0.0065(6) -0.0011(6) -0.0063(6)
C2 0.0141(8) 0.0148(8) 0.0175(8) -0.0048(6) -0.0005(6) -0.0024(6)
C3 0.0152(8) 0.0164(8) 0.0230(9) -0.0043(7) -0.0033(6) -0.0036(7)
C4 0.0201(9) 0.0159(8) 0.0142(8) -0.0010(6) -0.0010(6) -0.0040(7)
C5 0.0187(8) 0.0239(9) 0.0163(8) -0.0054(7) -0.0029(7) -0.0023(7)
C6 0.0197(9) 0.0257(9) 0.0193(8) -0.0087(7) -0.0034(7) -0.0055(7)
C7 0.0275(10) 0.0421(11) 0.0180(9) -0.0133(8) 0.0010(7) -0.0136(9)
C8 0.0259(10) 0.0192(9) 0.0361(11) -0.0044(8) 0.0092(8) -0.0011(8)
C9 0.0227(9) 0.0152(8) 0.0202(8) -0.0049(7) -0.0003(7) -0.0012(7)
C10 0.0261(9) 0.0152(8) 0.0204(8) -0.0085(7) -0.0026(7) -0.0034(7)
C11 0.0254(9) 0.0208(9) 0.0214(9) -0.0062(7) -0.0020(7) -0.0094(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7113(16) . ?
S2 C1 1.7269(16) . ?
O1 C3 1.4197(19) . ?
O1 H1O 0.8400 . ?
O2 C5 1.418(2) . ?
O2 H2O 0.8400 . ?
N1 C1 1.349(2) . ?
N1 C4 1.4698(19) . ?
N1 C2 1.474(2) . ?
N2 C9 1.490(2) . ?
N2 C10 1.497(2) . ?
N2 C6 1.500(2) . ?
N2 H2N 0.9300 . ?
N3 C7 1.469(2) . ?
N3 C11 1.471(2) . ?
N3 C8 1.472(2) . ?
C2 C3 1.510(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.517(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.538(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.537(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.542(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C3 O1 H1O 109.5 . . ?
C5 O2 H2O 109.5 . . ?
C1 N1 C4 121.99(13) . . ?
C1 N1 C2 122.04(13) . . ?
C4 N1 C2 115.62(12) . . ?
C9 N2 C10 110.07(12) . . ?
C9 N2 C6 110.46(12) . . ?
C10 N2 C6 109.53(12) . . ?
C9 N2 H2N 108.9 . . ?
C10 N2 H2N 108.9 . . ?
C6 N2 H2N 108.9 . . ?
C7 N3 C11 108.63(13) . . ?
C7 N3 C8 108.91(14) . . ?
C11 N3 C8 108.38(13) . . ?
N1 C1 S1 120.26(12) . . ?
N1 C1 S2 119.38(12) . . ?
S1 C1 S2 120.36(9) . . ?
N1 C2 C3 110.20(12) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 C2 107.86(13) . . ?
O1 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O1 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N1 C4 C5 115.01(13) . . ?
N1 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
N1 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
O2 C5 C4 114.04(13) . . ?
O2 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
O2 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N2 C6 C7 107.70(13) . . ?
N2 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
N2 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N3 C7 C6 111.48(13) . . ?
N3 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N3 C8 C9 111.69(14) . . ?
N3 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 107.60(13) . . ?
N2 C9 H9A 110.2 . . ?
C8 C9 H9A 110.2 . . ?
N2 C9 H9B 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N2 C10 C11 107.41(12) . . ?
N2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
N2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
N3 C11 C10 111.61(13) . . ?
N3 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?

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
C4 N1 C1 S1 -172.87(11) . . . . ?
C2 N1 C1 S1 0.06(19) . . . . ?
C4 N1 C1 S2 6.76(19) . . . . ?
C2 N1 C1 S2 179.68(10) . . . . ?
C1 N1 C2 C3 -91.67(17) . . . . ?
C4 N1 C2 C3 81.68(16) . . . . ?
N1 C2 C3 O1 -176.74(12) . . . . ?
C1 N1 C4 C5 -91.94(17) . . . . ?
C2 N1 C4 C5 94.71(16) . . . . ?
N1 C4 C5 O2 -59.91(19) . . . . ?
C9 N2 C6 C7 61.65(17) . . . . ?
C10 N2 C6 C7 -59.74(17) . . . . ?
C11 N3 C7 C6 60.47(18) . . . . ?
C8 N3 C7 C6 -57.38(18) . . . . ?
N2 C6 C7 N3 -2.2(2) . . . . ?
C7 N3 C8 C9 60.46(19) . . . . ?
C11 N3 C8 C9 -57.55(19) . . . . ?
C10 N2 C9 C8 62.29(17) . . . . ?
C6 N2 C9 C8 -58.78(17) . . . . ?
N3 C8 C9 N2 -2.5(2) . . . . ?
C9 N2 C10 C11 -59.26(16) . . . . ?
C6 N2 C10 C11 62.37(16) . . . . ?
C7 N3 C11 C10 -57.61(17) . . . . ?
C8 N3 C11 C10 60.58(18) . . . . ?
N2 C10 C11 N3 -2.77(18) . . . . ?

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
_geom_hbond_publ_flag
O1 H1O S2 0.84 2.36 3.1613(12) 160 1_655 ?
O2 H2O N3 0.84 2.11 2.9341(18) 166 1_654 ?
N2 H2N S1 0.93 2.34 3.1874(14) 152 . ?
N2 H2N S2 0.93 2.75 3.4865(14) 137 . ?
C10 H10A O1 0.99 2.45 3.341(2) 149 2_756 ?
C11 H11A S1 0.99 2.84 3.7976(18) 164 1_455 ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.5
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.25 # 0.69 A from N3
_refine_diff_density_min         -0.32 # 0.80 A from S2
_refine_diff_density_rms         0.058

# Attachment '3.CIF'

data_3
_database_code_depnum_ccdc_archive 'CCDC 690734'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H13 N2, C4 H8 N O S2 '
_chemical_formula_sum            'C10 H21 N3 O S2'
_chemical_formula_weight         263.42

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                   11.8425(4)
_cell_length_b                   9.3648(3)
_cell_length_c                   12.1634(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.823(2)
_cell_angle_gamma                90
_cell_volume                     1291.22(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3106
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17781
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.053
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.1
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2957
_reflns_number_gt                2155
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97

_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)+(0.0653P)²+0.0615P] 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         2957
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.040
_refine_ls_wR_factor_ref         0.118
_refine_ls_wR_factor_gt          0.096
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_restrained_S_all      1.10
_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 0.54638(5) 0.32495(6) 0.11555(5) 0.02136(17) Uani 1 1 d . . .
S2 S 0.61748(5) 0.27612(6) 0.36879(5) 0.02094(17) Uani 1 1 d . . .
O1 O 0.31762(15) 0.42714(16) 0.49690(13) 0.0265(4) Uani 1 1 d . . .
H1 H 0.3321 0.5024 0.5360 0.040 Uiso 1 1 calc R . .
N1 N 0.39527(16) 0.31226(19) 0.23885(15) 0.0189(4) Uani 1 1 d . . .
N2 N 0.83539(16) 0.32986(18) 0.25274(15) 0.0195(4) Uani 1 1 d . . .
H2 H 0.7554 0.3294 0.2474 0.023 Uiso 1 1 calc R . .
N3 N 1.05292(16) 0.33140(19) 0.26726(15) 0.0195(4) Uani 1 1 d . . .
C1 C 0.50906(19) 0.3065(2) 0.23989(18) 0.0160(5) Uani 1 1 d . . .
C2 C 0.35734(19) 0.3001(2) 0.34302(18) 0.0199(5) Uani 1 1 d . . .
H2A H 0.4145 0.2408 0.4004 0.024 Uiso 1 1 calc R . .
H2B H 0.2795 0.2524 0.3243 0.024 Uiso 1 1 calc R . .
C3 C 0.3489(2) 0.4462(2) 0.39318(18) 0.0212(5) Uani 1 1 d . . .
H3A H 0.4256 0.4963 0.4092 0.025 Uiso 1 1 calc R . .
H3B H 0.2883 0.5043 0.3382 0.025 Uiso 1 1 calc R . .
C4 C 0.3014(2) 0.3365(3) 0.13197(19) 0.0254(5) Uani 1 1 d . . .
H4A H 0.3191 0.4225 0.0941 0.038 Uiso 1 1 calc R . .
H4B H 0.2261 0.3491 0.1492 0.038 Uiso 1 1 calc R . .
H4C H 0.2960 0.2541 0.0810 0.038 Uiso 1 1 calc R . .
C5 C 0.8846(2) 0.1831(2) 0.2848(2) 0.0215(5) Uani 1 1 d . . .
H5A H 0.8438 0.1131 0.2256 0.026 Uiso 1 1 calc R . .
H5B H 0.8736 0.1540 0.3593 0.026 Uiso 1 1 calc R . .
C6 C 1.0169(2) 0.1886(2) 0.2937(2) 0.0239(5) Uani 1 1 d . . .
H6A H 1.0634 0.1614 0.3724 0.029 Uiso 1 1 calc R . .
H6B H 1.0339 0.1185 0.2396 0.029 Uiso 1 1 calc R . .
C7 C 0.8974(2) 0.4336(2) 0.3444(2) 0.0241(5) Uani 1 1 d . . .
H7A H 0.8876 0.4049 0.4194 0.029 Uiso 1 1 calc R . .
H7B H 0.8642 0.5306 0.3256 0.029 Uiso 1 1 calc R . .
C8 C 1.02882(19) 0.4324(2) 0.3497(2) 0.0244(5) Uani 1 1 d . . .
H8A H 1.0527 0.5295 0.3332 0.029 Uiso 1 1 calc R . .
H8B H 1.0765 0.4060 0.4283 0.029 Uiso 1 1 calc R . .
C9 C 0.8502(2) 0.3738(3) 0.13954(19) 0.0239(5) Uani 1 1 d . . .
H9A H 0.8178 0.4708 0.1190 0.029 Uiso 1 1 calc R . .
H9B H 0.8077 0.3068 0.0786 0.029 Uiso 1 1 calc R . .
C10 C 0.9826(2) 0.3719(3) 0.1508(2) 0.0276(5) Uani 1 1 d . . .
H10A H 0.9977 0.3033 0.0948 0.033 Uiso 1 1 calc R . .
H10B H 1.0072 0.4678 0.1323 0.033 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
S1 0.0219(3) 0.0245(3) 0.0185(3) -0.0003(2) 0.0072(2) -0.0009(2)
S2 0.0169(3) 0.0244(3) 0.0192(3) -0.0012(2) 0.0016(2) 0.0021(2)
O1 0.0361(10) 0.0268(9) 0.0208(8) -0.0049(7) 0.0149(7) -0.0050(7)
N1 0.0154(10) 0.0250(11) 0.0150(9) -0.0018(7) 0.0020(7) 0.0007(7)
N2 0.0144(10) 0.0187(10) 0.0259(10) -0.0026(8) 0.0064(8) 0.0004(7)
N3 0.0185(10) 0.0196(10) 0.0209(10) -0.0017(8) 0.0065(8) -0.0011(7)
C1 0.0170(11) 0.0121(11) 0.0178(11) -0.0027(8) 0.0030(8) 0.0006(8)
C2 0.0164(11) 0.0243(13) 0.0191(11) 0.0005(9) 0.0053(9) -0.0015(9)
C3 0.0232(13) 0.0226(12) 0.0193(11) 0.0009(9) 0.0087(9) -0.0004(9)
C4 0.0167(12) 0.0346(14) 0.0218(12) -0.0018(10) 0.0004(9) 0.0010(10)
C5 0.0220(12) 0.0160(11) 0.0276(13) -0.0011(9) 0.0087(10) -0.0001(9)
C6 0.0229(13) 0.0200(13) 0.0304(13) -0.0028(9) 0.0105(10) 0.0024(9)
C7 0.0229(13) 0.0210(12) 0.0298(13) -0.0085(10) 0.0097(10) -0.0024(9)
C8 0.0191(12) 0.0196(12) 0.0324(13) -0.0067(10) 0.0044(10) -0.0007(9)
C9 0.0230(12) 0.0236(12) 0.0234(12) 0.0037(10) 0.0040(9) 0.0009(10)
C10 0.0206(12) 0.0375(15) 0.0250(12) 0.0041(11) 0.0069(10) -0.0009(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 C1 1.703(2) . ?
S2 C1 1.738(2) . ?
O1 C3 1.425(2) . ?
O1 H1 0.8400 . ?
N1 C1 1.345(3) . ?
N1 C4 1.463(3) . ?
N1 C2 1.466(3) . ?
N2 C9 1.495(3) . ?
N2 C5 1.500(3) . ?
N2 C7 1.501(3) . ?
N2 H2 0.9300 . ?
N3 C8 1.466(3) . ?
N3 C6 1.468(3) . ?
N3 C10 1.471(3) . ?
C2 C3 1.513(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.539(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.539(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.533(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C3 O1 H1 109.5 . . ?
C1 N1 C4 121.08(18) . . ?
C1 N1 C2 123.05(18) . . ?
C4 N1 C2 115.83(18) . . ?
C9 N2 C5 110.55(16) . . ?
C9 N2 C7 110.06(17) . . ?
C5 N2 C7 109.29(17) . . ?
C9 N2 H2 109.0 . . ?
C5 N2 H2 109.0 . . ?
C7 N2 H2 109.0 . . ?
C8 N3 C6 108.15(17) . . ?
C8 N3 C10 108.95(18) . . ?
C6 N3 C10 109.05(18) . . ?
N1 C1 S1 120.30(16) . . ?
N1 C1 S2 119.44(16) . . ?
S1 C1 S2 120.25(13) . . ?
N1 C2 C3 110.54(17) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 C2 107.95(17) . . ?
O1 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O1 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 107.37(17) . . ?
N2 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 . . ?
N2 C5 H5B 110.2 . . ?
C6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
N3 C6 C5 111.70(17) . . ?
N3 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 107.36(17) . . ?
N2 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
N2 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
N3 C8 C7 111.76(17) . . ?
N3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C10 107.72(17) . . ?
N2 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
N2 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N3 C10 C9 111.61(18) . . ?
N3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?

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
C4 N1 C1 S1 -0.9(3) . . . . ?
C2 N1 C1 S1 -178.72(15) . . . . ?
C4 N1 C1 S2 -179.50(16) . . . . ?
C2 N1 C1 S2 2.7(3) . . . . ?
C1 N1 C2 C3 91.8(2) . . . . ?
C4 N1 C2 C3 -86.1(2) . . . . ?
N1 C2 C3 O1 -177.12(16) . . . . ?
C9 N2 C5 C6 60.7(2) . . . . ?
C7 N2 C5 C6 -60.6(2) . . . . ?
C8 N3 C6 C5 60.0(2) . . . . ?
C10 N3 C6 C5 -58.3(2) . . . . ?
N2 C5 C6 N3 -0.7(2) . . . . ?
C9 N2 C7 C8 -60.0(2) . . . . ?
C5 N2 C7 C8 61.6(2) . . . . ?
C6 N3 C8 C7 -59.0(2) . . . . ?
C10 N3 C8 C7 59.4(2) . . . . ?
N2 C7 C8 N3 -0.9(3) . . . . ?
C5 N2 C9 C10 -59.6(2) . . . . ?
C7 N2 C9 C10 61.2(2) . . . . ?
C8 N3 C10 C9 -58.3(2) . . . . ?
C6 N3 C10 C9 59.6(2) . . . . ?
N2 C9 C10 N3 -1.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.36
_refine_diff_density_rms         0.078

# Attachment '4.CIF'

data_4
_database_code_depnum_ccdc_archive 'CCDC 690735'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H13 N2, C5 H10 N O S2 '
_chemical_formula_sum            'C11 H23 N3 O S2'
_chemical_formula_weight         277.44

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

_symmetry_cell_setting           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                   7.7319(2)
_cell_length_b                   9.5151(2)
_cell_length_c                   9.5940(2)
_cell_angle_alpha                84.292(1)
_cell_angle_beta                 77.195(1)
_cell_angle_gamma                85.278(1)
_cell_volume                     683.54(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3160
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16659
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.9
_diffrn_reflns_theta_max         27.5
_reflns_number_total             3141
_reflns_number_gt                2780
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and PLATON (Spek, 2003)'

_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)+(0.0600P)²+0.2276P] 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         3141
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.111
_refine_ls_wR_factor_gt          0.106
_refine_ls_goodness_of_fit_ref   1.18
_refine_ls_restrained_S_all      1.18
_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 0.81519(5) 0.41919(4) 0.22507(4) 0.01881(13) Uani 1 1 d . . .
S2 S 0.52145(5) 0.23312(4) 0.23615(4) 0.01719(13) Uani 1 1 d . . .
O1 O 0.69048(19) -0.19688(13) 0.43566(14) 0.0279(3) Uani 1 1 d . . .
H1 H 0.6326 -0.2173 0.5193 0.042 Uiso 1 1 calc R . .
N1 N 0.85085(17) 0.13860(14) 0.25068(13) 0.0129(3) Uani 1 1 d . . .
N2 N 0.40050(18) 0.56798(14) 0.23804(14) 0.0155(3) Uani 1 1 d . . .
H2 H 0.4785 0.4879 0.2308 0.019 Uiso 1 1 calc R . .
N3 N 0.18865(17) 0.78495(14) 0.25759(15) 0.0167(3) Uani 1 1 d . . .
C1 C 0.7407(2) 0.25409(16) 0.23938(16) 0.0136(3) Uani 1 1 d . . .
C2 C 0.7929(2) -0.00552(16) 0.26740(16) 0.0141(3) Uani 1 1 d . . .
H2A H 0.8892 -0.0689 0.2164 0.017 Uiso 1 1 calc R . .
H2B H 0.6880 -0.0077 0.2246 0.017 Uiso 1 1 calc R . .
C3 C 0.7461(2) -0.05701(17) 0.42456(17) 0.0182(3) Uani 1 1 d . . .
H3A H 0.8508 -0.0559 0.4679 0.022 Uiso 1 1 calc R . .
H3B H 0.6494 0.0056 0.4762 0.022 Uiso 1 1 calc R . .
C4 C 1.0416(2) 0.14807(17) 0.24343(17) 0.0150(3) Uani 1 1 d . . .
H4A H 1.0858 0.0650 0.2991 0.018 Uiso 1 1 calc R . .
H4B H 1.0594 0.2341 0.2874 0.018 Uiso 1 1 calc R . .
C5 C 1.1473(2) 0.1535(2) 0.09030(18) 0.0217(4) Uani 1 1 d . . .
H5A H 1.2735 0.1597 0.0893 0.033 Uiso 1 1 calc R . .
H5B H 1.1053 0.2367 0.0354 0.033 Uiso 1 1 calc R . .
H5C H 1.1315 0.0677 0.0470 0.033 Uiso 1 1 calc R . .
C6 C 0.2667(2) 0.55572(19) 0.1512(2) 0.0263(4) Uani 1 1 d . . .
H6A H 0.1964 0.4725 0.1889 0.032 Uiso 1 1 calc R . .
H6B H 0.3265 0.5436 0.0502 0.032 Uiso 1 1 calc R . .
C7 C 0.1446(2) 0.69189(18) 0.1599(2) 0.0228(4) Uani 1 1 d . . .
H7A H 0.1569 0.7422 0.0632 0.027 Uiso 1 1 calc R . .
H7B H 0.0194 0.6672 0.1938 0.027 Uiso 1 1 calc R . .
C8 C 0.3140(3) 0.5801(2) 0.39140(19) 0.0319(5) Uani 1 1 d . . .
H8A H 0.4039 0.5941 0.4471 0.038 Uiso 1 1 calc R . .
H8B H 0.2538 0.4927 0.4324 0.038 Uiso 1 1 calc R . .
C9 C 0.1776(3) 0.7080(2) 0.39828(19) 0.0266(4) Uani 1 1 d . . .
H9A H 0.0564 0.6748 0.4341 0.032 Uiso 1 1 calc R . .
H9B H 0.1997 0.7724 0.4665 0.032 Uiso 1 1 calc R . .
C10 C 0.5022(2) 0.69511(18) 0.1820(2) 0.0255(4) Uani 1 1 d . . .
H10A H 0.5582 0.6896 0.0792 0.031 Uiso 1 1 calc R . .
H10B H 0.5970 0.7012 0.2353 0.031 Uiso 1 1 calc R . .
C11 C 0.3712(2) 0.82538(18) 0.2017(2) 0.0243(4) Uani 1 1 d . . .
H11A H 0.4047 0.8855 0.2688 0.029 Uiso 1 1 calc R . .
H11B H 0.3783 0.8817 0.1083 0.029 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
S1 0.0183(2) 0.0122(2) 0.0260(2) 0.00058(16) -0.00589(16) -0.00081(15)
S2 0.0119(2) 0.0167(2) 0.0226(2) 0.00077(15) -0.00472(15) 0.00096(15)
O1 0.0415(8) 0.0164(6) 0.0233(6) 0.0009(5) 0.0011(6) -0.0121(5)
N1 0.0119(6) 0.0128(6) 0.0138(6) 0.0005(5) -0.0032(5) 0.0001(5)
N2 0.0159(7) 0.0136(6) 0.0164(6) -0.0019(5) -0.0035(5) 0.0044(5)
N3 0.0148(7) 0.0146(6) 0.0209(7) -0.0026(5) -0.0049(5) 0.0018(5)
C1 0.0137(7) 0.0155(7) 0.0103(7) 0.0001(5) -0.0013(5) 0.0006(6)
C2 0.0150(7) 0.0115(7) 0.0157(7) -0.0012(6) -0.0038(6) 0.0001(6)
C3 0.0225(8) 0.0145(8) 0.0173(8) -0.0002(6) -0.0028(6) -0.0047(6)
C4 0.0123(7) 0.0165(7) 0.0170(7) -0.0003(6) -0.0055(6) 0.0003(6)
C5 0.0129(8) 0.0325(10) 0.0189(8) 0.0013(7) -0.0035(6) -0.0011(6)
C6 0.0245(9) 0.0206(9) 0.0396(10) -0.0130(8) -0.0173(8) 0.0056(7)
C7 0.0214(9) 0.0195(8) 0.0315(9) -0.0064(7) -0.0141(7) 0.0045(7)
C8 0.0426(12) 0.0284(10) 0.0169(8) 0.0030(7) 0.0022(8) 0.0140(8)
C9 0.0305(10) 0.0255(9) 0.0192(8) -0.0019(7) 0.0007(7) 0.0091(7)
C10 0.0163(8) 0.0179(8) 0.0408(11) -0.0020(7) -0.0036(7) -0.0006(6)
C11 0.0170(8) 0.0141(8) 0.0408(10) -0.0006(7) -0.0051(7) -0.0004(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6998(16) . ?
S2 C1 1.7305(16) . ?
O1 C3 1.4188(19) . ?
O1 H1 0.8400 . ?
N1 C1 1.344(2) . ?
N1 C2 1.4602(19) . ?
N1 C4 1.4711(19) . ?
N2 C6 1.483(2) . ?
N2 C8 1.487(2) . ?
N2 C10 1.487(2) . ?
N2 H2 0.9300 . ?
N3 C9 1.459(2) . ?
N3 C7 1.461(2) . ?
N3 C11 1.463(2) . ?
C2 C3 1.512(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.513(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.537(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.540(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.534(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C3 O1 H1 109.5 . . ?
C1 N1 C2 123.18(13) . . ?
C1 N1 C4 122.18(13) . . ?
C2 N1 C4 114.61(12) . . ?
C6 N2 C8 111.03(15) . . ?
C6 N2 C10 109.42(14) . . ?
C8 N2 C10 109.30(14) . . ?
C6 N2 H2 109.0 . . ?
C8 N2 H2 109.0 . . ?
C10 N2 H2 109.0 . . ?
C9 N3 C7 109.02(14) . . ?
C9 N3 C11 108.91(14) . . ?
C7 N3 C11 108.37(13) . . ?
N1 C1 S1 120.88(12) . . ?
N1 C1 S2 119.16(12) . . ?
S1 C1 S2 119.95(9) . . ?
N1 C2 C3 110.11(12) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
O1 C3 C2 108.16(12) . . ?
O1 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O1 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N1 C4 C5 111.56(12) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 107.91(13) . . ?
N2 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
N2 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N3 C7 C6 111.16(14) . . ?
N3 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 107.56(14) . . ?
N2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
N2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
N3 C9 C8 111.28(13) . . ?
N3 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C11 107.61(14) . . ?
N2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
N2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
N3 C11 C10 111.49(14) . . ?
N3 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?

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
C2 N1 C1 S1 178.17(11) . . . . ?
C4 N1 C1 S1 -3.4(2) . . . . ?
C2 N1 C1 S2 -3.0(2) . . . . ?
C4 N1 C1 S2 175.41(11) . . . . ?
C1 N1 C2 C3 -94.12(17) . . . . ?
C4 N1 C2 C3 87.34(15) . . . . ?
N1 C2 C3 O1 179.92(13) . . . . ?
C1 N1 C4 C5 -86.93(18) . . . . ?
C2 N1 C4 C5 91.62(16) . . . . ?
C8 N2 C6 C7 62.19(19) . . . . ?
C10 N2 C6 C7 -58.54(18) . . . . ?
C9 N3 C7 C6 -56.65(19) . . . . ?
C11 N3 C7 C6 61.75(19) . . . . ?
N2 C6 C7 N3 -4.1(2) . . . . ?
C6 N2 C8 C9 -56.4(2) . . . . ?
C10 N2 C8 C9 64.42(19) . . . . ?
C7 N3 C9 C8 62.69(19) . . . . ?
C11 N3 C9 C8 -55.37(19) . . . . ?
N2 C8 C9 N3 -6.0(2) . . . . ?
C6 N2 C10 C11 63.32(18) . . . . ?
C8 N2 C10 C11 -58.45(19) . . . . ?
C9 N3 C11 C10 61.71(19) . . . . ?
C7 N3 C11 C10 -56.77(19) . . . . ?
N2 C10 C11 N3 -4.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.66
_refine_diff_density_rms         0.235

# Attachment '5.CIF'

data_5
_database_code_depnum_ccdc_archive 'CCDC 690736'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H16 N Na O5 S2 '
_chemical_formula_sum            'C5 H16 N Na O5 S2'
_chemical_formula_weight         257.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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           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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   14.4181(4)
_cell_length_b                   8.1107(2)
_cell_length_c                   19.0611(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2229.02(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2891
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19691
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.1
_diffrn_reflns_theta_max         27.5
_reflns_number_total             2557
_reflns_number_gt                2150
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and PLATON (Spek, 2003)'

_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)+(0.0292P)²+1.1201P] 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         2557
_refine_ls_number_parameters     151
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.039
_refine_ls_R_factor_gt           0.029
_refine_ls_wR_factor_ref         0.068
_refine_ls_wR_factor_gt          0.064
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_restrained_S_all      1.11
_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
Na Na 0.31374(4) 0.05872(7) 0.96776(3) 0.01483(15) Uani 1 1 d . . .
S1 S 0.48899(3) 0.04716(5) 0.588145(19) 0.01442(10) Uani 1 1 d . . .
S2 S 0.35080(2) 0.13177(5) 0.697627(19) 0.01348(10) Uani 1 1 d . . .
O1 O 0.77199(7) 0.14017(14) 0.64742(6) 0.0157(2) Uani 1 1 d D . .
H1O H 0.8087 0.1306 0.6814 0.024 Uiso 1 1 d D . .
O2 O 0.46447(7) 0.07988(15) 0.90893(5) 0.0170(2) Uani 1 1 d D . .
H2O H 0.5095 0.1134 0.9330 0.025 Uiso 1 1 d D . .
O3 O 0.24904(8) 0.12366(13) 1.08396(5) 0.0183(2) Uani 1 1 d D . .
H3O H 0.2198 0.0552 1.1085 0.027 Uiso 1 1 d D . .
H4O H 0.2781 0.1903 1.1096 0.027 Uiso 1 1 d D . .
O4 O 0.17593(8) -0.13415(14) 0.97706(6) 0.0176(2) Uani 1 1 d D . .
H5O H 0.1455 -0.1159 1.0138 0.026 Uiso 1 1 d D . .
H6O H 0.1403 -0.1183 0.9428 0.026 Uiso 1 1 d D . .
O5 O 0.38647(7) -0.18637(13) 1.01113(6) 0.0165(2) Uani 1 1 d D . .
H7O H 0.3492 -0.2448 1.0342 0.025 Uiso 1 1 d D . .
H8O H 0.4175 -0.2469 0.9841 0.025 Uiso 1 1 d D . .
N1 N 0.53311(8) 0.10946(15) 0.72106(6) 0.0105(2) Uani 1 1 d . . .
C1 C 0.46486(10) 0.09812(17) 0.67304(8) 0.0110(3) Uani 1 1 d . . .
C2 C 0.62923(10) 0.06124(18) 0.70433(8) 0.0117(3) Uani 1 1 d . . .
H2A H 0.6281 -0.0325 0.6711 0.014 Uiso 1 1 calc R . .
H2B H 0.6603 0.0236 0.7478 0.014 Uiso 1 1 calc R . .
C3 C 0.68517(10) 0.20169(18) 0.67226(8) 0.0130(3) Uani 1 1 d . . .
H3A H 0.6501 0.2513 0.6329 0.016 Uiso 1 1 calc R . .
H3B H 0.6960 0.2883 0.7079 0.016 Uiso 1 1 calc R . .
C4 C 0.51727(10) 0.16709(18) 0.79321(7) 0.0116(3) Uani 1 1 d . . .
H4A H 0.4647 0.2455 0.7937 0.014 Uiso 1 1 calc R . .
H4B H 0.5731 0.2262 0.8101 0.014 Uiso 1 1 calc R . .
C5 C 0.49614(10) 0.02365(19) 0.84256(8) 0.0138(3) Uani 1 1 d . . .
H5A H 0.4482 -0.0477 0.8211 0.017 Uiso 1 1 calc R . .
H5B H 0.5529 -0.0434 0.8491 0.017 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
Na 0.0148(3) 0.0167(3) 0.0130(3) -0.0001(2) -0.0001(2) 0.0018(2)
S1 0.01312(18) 0.0201(2) 0.01004(18) -0.00227(14) 0.00100(14) -0.00074(15)
S2 0.00883(17) 0.01876(19) 0.01284(19) -0.00012(14) 0.00072(13) 0.00116(14)
O1 0.0078(5) 0.0260(6) 0.0131(5) -0.0004(5) 0.0010(4) 0.0026(4)
O2 0.0129(5) 0.0285(6) 0.0095(5) -0.0007(4) 0.0011(4) -0.0026(5)
O3 0.0211(6) 0.0186(6) 0.0151(6) 0.0001(5) 0.0005(5) -0.0066(5)
O4 0.0169(6) 0.0227(6) 0.0133(5) -0.0009(5) -0.0031(4) 0.0023(5)
O5 0.0149(5) 0.0182(5) 0.0163(6) 0.0013(4) 0.0015(4) 0.0010(5)
N1 0.0084(6) 0.0126(6) 0.0105(6) -0.0005(5) 0.0009(5) 0.0005(5)
C1 0.0123(7) 0.0081(6) 0.0124(7) 0.0004(5) 0.0007(5) -0.0014(6)
C2 0.0084(6) 0.0143(7) 0.0126(7) 0.0005(5) 0.0002(5) 0.0012(6)
C3 0.0094(7) 0.0158(7) 0.0137(7) 0.0005(6) 0.0011(5) 0.0013(6)
C4 0.0109(7) 0.0135(7) 0.0103(7) -0.0024(5) -0.0002(5) -0.0010(6)
C5 0.0146(7) 0.0145(7) 0.0121(7) -0.0001(6) 0.0011(6) 0.0000(6)

_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
Na O1 2.3704(12) 8_557 ?
Na O5 2.3947(12) . ?
Na O2 2.4515(12) . ?
Na O3 2.4604(12) . ?
Na O4 2.5018(13) 6_665 ?
Na O4 2.5350(13) . ?
S1 C1 1.7060(15) . ?
S2 C1 1.7316(15) . ?
O1 C3 1.4284(17) . ?
O1 H1O 0.8398 . ?
O2 C5 1.4202(18) . ?
O2 H2O 0.8399 . ?
O3 H3O 0.8400 . ?
O3 H4O 0.8401 . ?
O4 H5O 0.8402 . ?
O4 H6O 0.8402 . ?
O5 H7O 0.8400 . ?
O5 H8O 0.8401 . ?
N1 C1 1.3470(19) . ?
N1 C4 1.4704(18) . ?
N1 C2 1.4748(18) . ?
C2 C3 1.524(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C4 1.527(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na O5 131.48(4) 8_557 . ?
O1 Na O2 77.40(4) 8_557 . ?
O5 Na O2 80.09(4) . . ?
O1 Na O3 132.68(4) 8_557 . ?
O5 Na O3 91.89(4) . . ?
O2 Na O3 137.13(4) . . ?
O1 Na O4 78.65(4) 8_557 6_665 ?
O5 Na O4 140.90(5) . 6_665 ?
O2 Na O4 84.83(4) . 6_665 ?
O3 Na O4 75.26(4) . 6_665 ?
O1 Na O4 92.16(4) 8_557 . ?
O5 Na O4 78.86(4) . . ?
O2 Na O4 140.35(4) . . ?
O3 Na O4 76.82(4) . . ?
O4 Na O4 131.01(4) 6_665 . ?
C3 O1 Na 128.82(9) . 8_657 ?
C3 O1 H1O 109.2 . . ?
Na O1 H1O 121.9 8_657 . ?
C5 O2 Na 132.06(9) . . ?
C5 O2 H2O 110.0 . . ?
Na O2 H2O 117.3 . . ?
Na O3 H3O 123.5 . . ?
Na O3 H4O 118.2 . . ?
H3O O3 H4O 110.5 . . ?
Na O4 Na 124.25(5) 6_655 . ?
Na O4 H5O 105.4 6_655 . ?
Na O4 H5O 111.1 . . ?
Na O4 H6O 97.7 6_655 . ?
Na O4 H6O 109.3 . . ?
H5O O4 H6O 107.5 . . ?
Na O5 H7O 111.7 . . ?
Na O5 H8O 120.4 . . ?
H7O O5 H8O 109.3 . . ?
C1 N1 C4 122.94(12) . . ?
C1 N1 C2 121.43(12) . . ?
C4 N1 C2 115.62(11) . . ?
N1 C1 S1 120.80(11) . . ?
N1 C1 S2 119.94(11) . . ?
S1 C1 S2 119.25(9) . . ?
N1 C2 C3 112.70(12) . . ?
N1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 C2 109.61(12) . . ?
O1 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
O1 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O2 C5 C4 111.61(12) . . ?
O2 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
O2 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1 C4 C5 111.41(12) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.50
_refine_diff_density_rms         0.139

# Attachment '6.CIF'

data_6
_database_code_depnum_ccdc_archive 'CCDC 690737'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H16 N Na O3 S2 '
_chemical_formula_sum            'C6 H16 N Na O3 S2 '
_chemical_formula_weight         237.33

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   26.8102(15)
_cell_length_b                   5.8617(2)
_cell_length_c                   14.8147(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.278(2)
_cell_angle_gamma                90
_cell_volume                     2234.85(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    24718
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            10254
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.043
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.2
_diffrn_reflns_theta_max         25.0
_reflns_number_total             1948
_reflns_number_gt                1651
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97

_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)+(0.0356P)²+42.6193P] 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         1948
_refine_ls_number_parameters     133
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.070
_refine_ls_R_factor_gt           0.059
_refine_ls_wR_factor_ref         0.170
_refine_ls_wR_factor_gt          0.165
_refine_ls_goodness_of_fit_ref   1.14
_refine_ls_restrained_S_all      1.14
_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 0.68585(5) 1.2466(2) 0.26623(9) 0.0148(3) Uani 1 1 d . . .
S2 S 0.59583(5) 1.0909(2) 0.33253(9) 0.0150(3) Uani 1 1 d . . .
Na Na 0.78079(8) 1.0073(3) 0.04792(14) 0.0152(5) Uani 1 1 d . . .
O1 O 0.69461(14) 0.8577(7) 0.0166(2) 0.0153(8) Uani 1 1 d D . .
H1O H 0.6703 0.8749 -0.0330 0.023 Uiso 1 1 d D . .
O2 O 0.86763(15) 1.0872(7) 0.0742(3) 0.0207(9) Uani 1 1 d D . .
H2O H 0.8783 1.2165 0.0955 0.031 Uiso 1 1 d D . .
H3O H 0.8883 0.9833 0.0999 0.031 Uiso 1 1 d D . .
O3 O 0.74956(14) 1.3343(7) 0.1082(3) 0.0178(9) Uani 1 1 d D . .
H4O H 0.7667 1.4554 0.1223 0.027 Uiso 1 1 d D . .
H5O H 0.7234 1.3347 0.1287 0.027 Uiso 1 1 d D . .
N1 N 0.60464(17) 1.0125(7) 0.1605(3) 0.0119(9) Uani 1 1 d . . .
C1 C 0.62730(19) 1.1065(9) 0.2448(3) 0.0122(11) Uani 1 1 d . . .
C2 C 0.6295(2) 1.0216(10) 0.0840(3) 0.0143(11) Uani 1 1 d . . .
H2A H 0.6469 1.1713 0.0855 0.017 Uiso 1 1 calc R . .
H2B H 0.6025 1.0089 0.0230 0.017 Uiso 1 1 calc R . .
C3 C 0.6697(2) 0.8317(10) 0.0907(4) 0.0159(11) Uani 1 1 d . . .
H3A H 0.6961 0.8387 0.1526 0.019 Uiso 1 1 calc R . .
H3B H 0.6523 0.6812 0.0851 0.019 Uiso 1 1 calc R . .
C4 C 0.5531(2) 0.9007(10) 0.1376(4) 0.0171(12) Uani 1 1 d . . .
H4A H 0.5334 0.9429 0.0727 0.021 Uiso 1 1 calc R . .
H4B H 0.5337 0.9601 0.1806 0.021 Uiso 1 1 calc R . .
C5 C 0.5554(2) 0.6432(11) 0.1453(5) 0.0255(14) Uani 1 1 d . . .
H5A H 0.5758 0.5986 0.2094 0.031 Uiso 1 1 calc R . .
H5B H 0.5730 0.5809 0.1002 0.031 Uiso 1 1 calc R . .
C6 C 0.5012(2) 0.5447(12) 0.1245(5) 0.0332(16) Uani 1 1 d . . .
H6A H 0.5033 0.3781 0.1293 0.050 Uiso 1 1 calc R . .
H6B H 0.4811 0.5880 0.0607 0.050 Uiso 1 1 calc R . .
H6C H 0.4840 0.6043 0.1699 0.050 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
S1 0.0153(6) 0.0175(7) 0.0119(6) -0.0011(5) 0.0044(5) -0.0021(5)
S2 0.0178(7) 0.0172(7) 0.0117(6) -0.0008(5) 0.0070(5) -0.0009(5)
Na 0.0150(10) 0.0151(11) 0.0158(10) -0.0006(9) 0.0049(8) -0.0008(8)
O1 0.0156(19) 0.021(2) 0.0106(17) -0.0003(16) 0.0061(14) 0.0002(16)
O2 0.020(2) 0.018(2) 0.021(2) 0.0008(18) 0.0021(16) -0.0020(17)
O3 0.019(2) 0.020(2) 0.0169(19) -0.0033(17) 0.0090(16) -0.0037(16)
N1 0.016(2) 0.012(2) 0.009(2) -0.0008(17) 0.0055(17) 0.0023(17)
C1 0.013(3) 0.012(3) 0.011(2) 0.004(2) 0.004(2) 0.005(2)
C2 0.017(3) 0.021(3) 0.006(2) -0.002(2) 0.004(2) 0.002(2)
C3 0.019(3) 0.019(3) 0.012(2) 0.000(2) 0.010(2) 0.001(2)
C4 0.012(3) 0.029(3) 0.010(2) -0.004(2) 0.002(2) 0.001(2)
C5 0.020(3) 0.024(3) 0.033(3) -0.004(3) 0.008(3) -0.005(2)
C6 0.026(3) 0.035(4) 0.040(4) -0.008(3) 0.011(3) -0.014(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 C1 1.720(5) . ?
S1 Na 3.055(2) 4_655 ?
S2 C1 1.739(5) . ?
Na O2 2.299(4) . ?
Na O3 2.365(4) . ?
Na O1 2.392(4) . ?
Na O3 2.412(4) 7_675 ?
Na O1 2.506(4) 7_665 ?
Na S1 3.055(2) 4_645 ?
Na Na 3.394(4) 7_675 ?
Na Na 3.540(4) 7_665 ?
O1 C3 1.444(6) . ?
O1 H1O 0.8400 . ?
O2 H2O 0.8400 . ?
O2 H3O 0.8400 . ?
O3 H4O 0.8400 . ?
O3 H5O 0.8400 . ?
N1 C1 1.344(7) . ?
N1 C2 1.469(6) . ?
N1 C4 1.481(7) . ?
C2 C3 1.532(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.513(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.513(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 Na 115.25(18) . 4_655 ?
O2 Na O3 102.71(16) . . ?
O2 Na O1 170.06(17) . . ?
O3 Na O1 86.87(15) . . ?
O2 Na O3 97.90(15) . 7_675 ?
O3 Na O3 89.45(14) . 7_675 ?
O1 Na O3 84.68(14) . 7_675 ?
O2 Na O1 82.89(15) . 7_665 ?
O3 Na O1 174.28(15) . 7_665 ?
O1 Na O1 87.49(14) . 7_665 ?
O3 Na O1 90.96(14) 7_675 7_665 ?
O2 Na S1 85.56(12) . 4_645 ?
O3 Na S1 96.33(12) . 4_645 ?
O1 Na S1 90.81(11) . 4_645 ?
O3 Na S1 172.47(13) 7_675 4_645 ?
O1 Na S1 82.81(10) 7_665 4_645 ?
O2 Na Na 104.53(14) . 7_675 ?
O3 Na Na 45.29(10) . 7_675 ?
O1 Na Na 84.03(12) . 7_675 ?
O3 Na Na 44.16(10) 7_675 7_675 ?
O1 Na Na 134.84(13) 7_665 7_675 ?
S1 Na Na 141.39(10) 4_645 7_675 ?
O2 Na Na 125.31(15) . 7_665 ?
O3 Na Na 131.88(14) . 7_665 ?
O1 Na Na 45.02(10) . 7_665 ?
O3 Na Na 87.08(12) 7_675 7_665 ?
O1 Na Na 42.47(9) 7_665 7_665 ?
S1 Na Na 85.47(8) 4_645 7_665 ?
Na Na Na 115.40(11) 7_675 7_665 ?
C3 O1 Na 121.3(3) . . ?
C3 O1 Na 115.3(3) . 7_665 ?
Na O1 Na 92.51(14) . 7_665 ?
C3 O1 H1O 105.5 . . ?
Na O1 H1O 126.6 . . ?
Na O1 H1O 89.5 7_665 . ?
Na O2 H2O 118.1 . . ?
Na O2 H3O 116.0 . . ?
H2O O2 H3O 111.8 . . ?
Na O3 Na 90.55(14) . 7_675 ?
Na O3 H4O 123.5 . . ?
Na O3 H4O 85.8 7_675 . ?
Na O3 H5O 124.0 . . ?
Na O3 H5O 104.7 7_675 . ?
H4O O3 H5O 111.3 . . ?
C1 N1 C2 121.1(4) . . ?
C1 N1 C4 123.0(4) . . ?
C2 N1 C4 115.9(4) . . ?
N1 C1 S1 121.2(4) . . ?
N1 C1 S2 119.0(4) . . ?
S1 C1 S2 119.7(3) . . ?
N1 C2 C3 112.7(4) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 C2 109.9(4) . . ?
O1 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
O1 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N1 C4 C5 114.1(4) . . ?
N1 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 110.4(5) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Na O1 C3 107.5(10) . . . . ?
O3 Na O1 C3 -57.3(4) . . . . ?
O3 Na O1 C3 -147.0(4) 7_675 . . . ?
O1 Na O1 C3 121.8(4) 7_665 . . . ?
S1 Na O1 C3 39.0(4) 4_645 . . . ?
Na Na O1 C3 -102.6(4) 7_675 . . . ?
Na Na O1 C3 121.8(4) 7_665 . . . ?
O2 Na O1 Na -14.3(10) . . . 7_665 ?
O3 Na O1 Na -179.06(16) . . . 7_665 ?
O3 Na O1 Na 91.20(14) 7_675 . . 7_665 ?
O1 Na O1 Na 0.0 7_665 . . 7_665 ?
S1 Na O1 Na -82.77(10) 4_645 . . 7_665 ?
Na Na O1 Na 135.58(13) 7_675 . . 7_665 ?
O2 Na O3 Na 97.97(16) . . . 7_675 ?
O1 Na O3 Na -84.70(14) . . . 7_675 ?
O3 Na O3 Na 0.000(1) 7_675 . . 7_675 ?
O1 Na O3 Na -94.1(16) 7_665 . . 7_675 ?
S1 Na O3 Na -175.17(12) 4_645 . . 7_675 ?
Na Na O3 Na -85.59(19) 7_665 . . 7_675 ?
C2 N1 C1 S1 1.3(7) . . . . ?
C4 N1 C1 S1 -176.8(4) . . . . ?
C2 N1 C1 S2 179.8(4) . . . . ?
C4 N1 C1 S2 1.7(7) . . . . ?
Na S1 C1 N1 170.5(4) 4_655 . . . ?
Na S1 C1 S2 -7.9(4) 4_655 . . . ?
C1 N1 C2 C3 83.5(6) . . . . ?
C4 N1 C2 C3 -98.2(5) . . . . ?
Na O1 C3 C2 103.8(4) . . . . ?
Na O1 C3 C2 -146.1(3) 7_665 . . . ?
N1 C2 C3 O1 -176.9(4) . . . . ?
C1 N1 C4 C5 -98.9(6) . . . . ?
C2 N1 C4 C5 82.8(6) . . . . ?
N1 C4 C5 C6 177.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.0
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.41
_refine_diff_density_rms         0.109


# Attachment '7.CIF'

data_7
_database_code_depnum_ccdc_archive 'CCDC 690738'

# _audit_creation_method SHELXL-97
_chemical_name_systematic        
;
Potassium bis(ethanol)dithiocarbamate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 K N O2 S2 '
_chemical_formula_sum            'C5 H10 K N O2 S2'
_chemical_formula_weight         219.36

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'
K K 0.2009 0.2494 '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 m'
_symmetry_space_group_name_Hall  '-P 2c 2b'

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

_cell_length_a                   7.6968(2)
_cell_length_b                   14.1288(3)
_cell_length_c                   8.0270(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     872.92(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1168
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       slab
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    1.037
_exptl_absorpt_correction_type   multi-scan
# compare SADABS Tmin/max (below) with calc. 0.5994/0.9034
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_process_details   'SADAB (Sheldrick, 2003)'

_exptl_special_details           
;
Unit cell determined with DirAx (Duisenberg, 1992; Duisenberg et al. 2000)
but refined with the DENZO/COLLECT HKL package.

Refs as:
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J.
(2000). J. Appl. Cryst. 33, 893-898.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6688
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.8
_diffrn_reflns_theta_max         27.5
_reflns_number_total             1065
_reflns_number_gt                1029
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

_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.

Final refinement in the space group Pbcm after initial structure solution
and expansion in the space group Pca21.
;

_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)+(0.0059P)²+1.4274P] 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         1065
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.029
_refine_ls_R_factor_gt           0.027
_refine_ls_wR_factor_ref         0.068
_refine_ls_wR_factor_gt          0.067
_refine_ls_goodness_of_fit_ref   1.31
_refine_ls_restrained_S_all      1.31
_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
K1 K 0.88524(7) 0.2500 0.0000 0.01424(15) Uani 1 2 d S . .
S1 S 0.89754(8) 0.43149(4) 0.2500 0.01120(16) Uani 1 2 d S . .
S2 S 0.55859(8) 0.33318(4) 0.2500 0.01191(16) Uani 1 2 d S . .
O1 O 0.8352(3) 0.74370(17) 0.2905(3) 0.0143(8) Uani 0.50 1 d P . .
H1 H 0.7734 0.7775 0.2280 0.021 Uiso 0.50 1 d PR . .
O2 O 0.1492(2) 0.60918(13) 0.2500 0.0124(4) Uani 1 2 d S . .
H2 H 0.0790 0.5663 0.2232 0.019 Uiso 0.50 1 d PR . .
N1 N 0.5973(4) 0.5195(2) 0.1906(4) 0.0083(6) Uani 0.50 1 d P . .
C1 C 0.6761(4) 0.4363(2) 0.2500 0.0243(7) Uani 1 2 d S . .
C2 C 0.6965(5) 0.6078(3) 0.1673(5) 0.0108(7) Uani 0.50 1 d P . .
H2A H 0.6269 0.6517 0.0981 0.013 Uiso 0.50 1 calc PR . .
H2B H 0.8044 0.5931 0.1054 0.013 Uiso 0.50 1 calc PR . .
C3 C 0.7443(5) 0.6573(3) 0.3287(5) 0.0121(7) Uani 0.50 1 d P . .
H3A H 0.6379 0.6717 0.3932 0.014 Uiso 0.50 1 calc PR . .
H3B H 0.8192 0.6157 0.3971 0.014 Uiso 0.50 1 calc PR . .
C4 C 0.4102(4) 0.5279(2) 0.1537(5) 0.0106(7) Uani 0.50 1 d P . .
H4A H 0.3633 0.4647 0.1247 0.013 Uiso 0.50 1 calc PR . .
H4B H 0.3939 0.5699 0.0562 0.013 Uiso 0.50 1 calc PR . .
C5 C 0.3098(5) 0.5676(3) 0.3013(5) 0.0141(8) Uani 0.50 1 d P . .
H5A H 0.2862 0.5162 0.3818 0.017 Uiso 0.50 1 calc PR . .
H5B H 0.3814 0.6160 0.3581 0.017 Uiso 0.50 1 calc PR . .

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
K1 0.0170(3) 0.0101(3) 0.0155(3) -0.0009(2) 0.000 0.000
S1 0.0058(3) 0.0065(3) 0.0213(3) 0.000 0.000 0.0008(2)
S2 0.0092(3) 0.0069(3) 0.0197(3) 0.000 0.000 -0.0031(2)
O1 0.0094(10) 0.0069(10) 0.027(2) 0.0016(9) -0.0022(10) -0.0014(9)
O2 0.0056(8) 0.0083(9) 0.0232(10) 0.000 0.000 -0.0001(7)
N1 0.0050(13) 0.0047(12) 0.0152(13) -0.0004(10) -0.0005(10) -0.0004(10)
C1 0.0091(13) 0.0063(12) 0.057(2) 0.000 0.000 0.0013(10)
C2 0.0117(17) 0.0057(17) 0.0151(19) 0.0027(15) -0.0006(15) -0.0010(15)
C3 0.0109(17) 0.0077(18) 0.0176(19) 0.0008(15) 0.0017(15) -0.0014(15)
C4 0.0069(16) 0.0094(15) 0.0155(18) -0.0010(14) -0.0021(14) 0.0027(13)
C5 0.0084(16) 0.0191(18) 0.0146(18) -0.0027(13) -0.0020(12) 0.0015(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.

Data below corresponds to an ordered structure, effectively in the space
group Pbc21, with no trace of the disorder over two mirror plane related
orientations of the bis(ethanol)amino substituent of the dithiocarbamate.
;

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
K1 O1 2.732(2) 2_764 ?
K1 O2 2.8382(13) 5_665 ?
K1 O2 2.8382(13) 7_656 ?
K1 O1 3.174(2) 4_745 ?
K1 S1 3.2575(5) . ?
K1 S1 3.2575(5) 3_554 ?
K1 S2 3.4248(7) 3_554 ?
K1 S2 3.4248(7) . ?
S1 C1 1.706(3) . ?
S1 K1 3.2575(5) 6_556 ?
S2 C1 1.715(3) . ?
S2 K1 3.4248(7) 6_556 ?
O1 C3 1.440(5) . ?
O1 H1 0.8400 . ?
O2 C5 1.429(4) . ?
O2 H2 0.8400 . ?
N1 C1 1.406(4) . ?
N1 C2 1.475(5) . ?
N1 C4 1.475(4) . ?
C2 C3 1.518(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 O2 67.38(6) 2_764 5_665 ?
O1 K1 O2 122.11(6) 2_764 7_656 ?
O2 K1 O2 169.29(8) 5_665 7_656 ?
O1 K1 O1 85.37(6) 2_764 4_745 ?
O2 K1 O1 127.04(6) 5_665 4_745 ?
O2 K1 O1 61.59(5) 7_656 4_745 ?
O1 K1 S1 109.31(5) 2_764 . ?
O2 K1 S1 83.48(3) 5_665 . ?
O2 K1 S1 96.83(3) 7_656 . ?
O1 K1 S1 63.24(4) 4_745 . ?
O1 K1 S1 67.89(5) 2_764 3_554 ?
O2 K1 S1 96.83(3) 5_665 3_554 ?
O2 K1 S1 83.48(3) 7_656 3_554 ?
O1 K1 S1 114.26(5) 4_745 3_554 ?
S1 K1 S1 176.67(3) . 3_554 ?
O1 K1 S2 103.21(5) 2_764 3_554 ?
O2 K1 S2 75.98(3) 5_665 3_554 ?
O2 K1 S2 96.04(3) 7_656 3_554 ?
O1 K1 S2 156.70(5) 4_745 3_554 ?
S1 K1 S2 130.72(2) . 3_554 ?
S1 K1 S2 52.428(15) 3_554 3_554 ?
O1 K1 S2 158.06(5) 2_764 . ?
O2 K1 S2 96.04(3) 5_665 . ?
O2 K1 S2 75.98(3) 7_656 . ?
O1 K1 S2 94.40(4) 4_745 . ?
S1 K1 S2 52.429(15) . . ?
S1 K1 S2 130.72(2) 3_554 . ?
S2 K1 S2 85.54(2) 3_554 . ?
C1 S1 K1 90.14(8) . . ?
C1 S1 K1 90.14(8) . 6_556 ?
K1 S1 K1 76.056(14) . 6_556 ?
C1 S2 K1 84.51(8) . 6_556 ?
C1 S2 K1 84.51(8) . . ?
K1 S2 K1 71.740(16) 6_556 . ?
C3 O1 K1 106.2(2) . 2_765 ?
C3 O1 K1 120.7(2) . 5_765 ?
K1 O1 K1 85.27(6) 2_765 5_765 ?
C3 O1 H1 109.5 . . ?
K1 O1 H1 142.7 2_765 . ?
K1 O1 H1 85.9 5_765 . ?
C5 O2 K1 99.50(16) . 2_665 ?
C5 O2 K1 124.91(18) . 5_665 ?
K1 O2 K1 89.99(5) 2_665 5_665 ?
C5 O2 H2 109.5 . . ?
K1 O2 H2 128.8 2_665 . ?
K1 O2 H2 105.4 5_665 . ?
C1 N1 C2 121.8(3) . . ?
C1 N1 C4 123.8(3) . . ?
C2 N1 C4 114.3(3) . . ?
N1 C1 S1 117.7(2) . . ?
N1 C1 S2 118.9(2) . . ?
S1 C1 S2 119.54(17) . . ?
N1 C2 C3 114.1(3) . . ?
N1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
O1 C3 C2 109.1(3) . . ?
O1 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
O1 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C5 111.7(3) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 C4 111.5(3) . . ?
O2 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
O2 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?

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
_geom_hbond_publ_flag
O1 H1 S2 0.84 2.68 3.300(2) 131.9 4_655 Y
O2 H2 S1 0.84 2.37 3.1708(19) 159.2 1_455 y

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.0
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.37
_refine_diff_density_rms         0.065

# Attachment '8.CIF'

data_8
_database_code_depnum_ccdc_archive 'CCDC 690739'

# 06src1138

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Cesium bis(ethanol)dithiocarbamate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 Cs N O2 S2'
_chemical_formula_sum            'C5 H10 Cs N O2 S2'
_chemical_formula_weight         313.17

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'
Cs Cs -0.3680 2.1192 '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           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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   16.0465(4)
_cell_length_b                   14.2446(3)
_cell_length_c                   8.4274(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1926.30(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2506
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    4.233
_exptl_absorpt_correction_type   multi-scan
# compare SADABS Tmin/max (below) with calc 0.2823/0.6769
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_T_max  0.677
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
;
Unit cell determined with DirAx (Duisenberg, 1992; Duisenberg et al. 2000)
but refined with the DENZO/COLLECT HKL package.

Refs as:
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J.
(2000). J. Appl. Cryst. 33, 893-898.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        '< 1'
_diffrn_reflns_number            17609
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.019
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         27.5
_reflns_number_total             2207
_reflns_number_gt                1918
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL-97

_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+1.856P] 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     SHELXL
_refine_ls_extinction_coef       0.00301(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2207
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.023
_refine_ls_R_factor_gt           0.018
_refine_ls_wR_factor_ref         0.044
_refine_ls_wR_factor_gt          0.042
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_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
Cs1 Cs 0.450582(8) 0.252704(8) 0.559747(14) 0.01380(7) Uani 1 1 d . . .
S1 S 0.43510(3) 0.44892(4) 0.83367(7) 0.01638(12) Uani 1 1 d . . .
S2 S 0.27909(3) 0.34358(3) 0.77000(6) 0.01561(12) Uani 1 1 d . . .
O1 O 0.40177(10) 0.75563(9) 0.69431(17) 0.0164(3) Uani 1 1 d . . .
H1O H 0.3644 0.7956 0.7118 0.025 Uiso 1 1 calc R . .
O2 O 0.06752(9) 0.58955(11) 0.81341(17) 0.0164(3) Uani 1 1 d . . .
H2O H 0.0304 0.5510 0.7875 0.025 Uiso 1 1 calc R . .
N1 N 0.28964(10) 0.53074(11) 0.77010(19) 0.0112(3) Uani 1 1 d . . .
C1 C 0.33086(13) 0.44889(14) 0.7878(2) 0.0120(4) Uani 1 1 d . . .
C2 C 0.32823(13) 0.62188(13) 0.8063(2) 0.0134(4) Uani 1 1 d . . .
H2A H 0.3732 0.6128 0.8853 0.016 Uiso 1 1 calc R . .
H2B H 0.2859 0.6641 0.8534 0.016 Uiso 1 1 calc R . .
C3 C 0.36425(13) 0.66729(13) 0.6578(2) 0.0147(4) Uani 1 1 d . . .
H3A H 0.4065 0.6251 0.6105 0.018 Uiso 1 1 calc R . .
H3B H 0.3193 0.6766 0.5788 0.018 Uiso 1 1 calc R . .
C4 C 0.20272(12) 0.53702(14) 0.7166(2) 0.0132(4) Uani 1 1 d . . .
H4A H 0.1897 0.4821 0.6490 0.016 Uiso 1 1 calc R . .
H4B H 0.1957 0.5942 0.6512 0.016 Uiso 1 1 calc R . .
C5 C 0.14156(13) 0.54020(15) 0.8550(2) 0.0177(4) Uani 1 1 d . . .
H5A H 0.1271 0.4754 0.8870 0.021 Uiso 1 1 calc R . .
H5B H 0.1683 0.5715 0.9467 0.021 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
Cs1 0.01516(10) 0.01375(9) 0.01250(9) 0.00010(4) 0.00173(4) 0.00033(4)
S1 0.0101(2) 0.0143(2) 0.0248(3) 0.0051(2) -0.0025(2) -0.00068(19)
S2 0.0127(2) 0.0107(2) 0.0235(3) -0.0011(2) 0.0022(2) -0.00259(19)
O1 0.0111(8) 0.0117(7) 0.0262(9) -0.0004(6) 0.0015(6) -0.0014(5)
O2 0.0088(7) 0.0170(7) 0.0236(8) -0.0039(6) -0.0017(6) 0.0004(6)
N1 0.0097(8) 0.0097(7) 0.0143(8) 0.0001(6) -0.0013(7) -0.0007(6)
C1 0.0123(10) 0.0131(9) 0.0106(9) 0.0001(7) 0.0024(8) -0.0013(8)
C2 0.0150(11) 0.0101(9) 0.0153(10) -0.0015(7) 0.0001(8) -0.0001(8)
C3 0.0139(11) 0.0121(9) 0.0182(10) 0.0000(8) -0.0005(8) -0.0012(8)
C4 0.0108(10) 0.0152(10) 0.0134(9) 0.0026(8) -0.0011(8) 0.0010(8)
C5 0.0147(11) 0.0214(10) 0.0171(10) 0.0026(8) 0.0010(9) 0.0038(9)

_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
# v. -x+1/2, 1-y, z-1/2
# ii. 1-x, y-1/2, -z+3/2
# iv. -x+1/2, y-1/2, z
# iii. 1-x, 1-y, 1-z
# i. x, -y+1/2, z-1/2
# i. x, -y+1/2, z-1/2
Cs1 O2 3.0730(14) 4_564 ?
Cs1 O1 3.1482(16) 3_646 ?
Cs1 O2 3.1711(15) 6_655 ?
Cs1 O1 3.1956(15) 5_666 ?
Cs1 S1 3.4555(5) 7_565 ?
Cs1 S2 3.5196(5) . ?
Cs1 S1 3.6335(6) . ?
Cs1 S2 3.9263(6) 7_565 ?
S1 C1 1.717(2) . ?
S2 C1 1.721(2) . ?
O1 C3 1.429(2) . ?
O1 H1O 0.8400 . ?
O2 C5 1.424(2) . ?
O2 H2O 0.8400 . ?
N1 C1 1.349(3) . ?
N1 C4 1.469(2) . ?
N1 C2 1.470(2) . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.525(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
# v. -x+1/2, 1-y, z-1/2; iv. -x+1/2, y-1/2, z
# iii. 1-x, 1-y, 1-z
# i. x, -y+1/2, z-1/2
# ii.1-x, y-1/2, -z+3/2; i. x, -y+1/2, z-1/2
O2 Cs1 O1 120.41(4) 4_564 3_646 ?
O2 Cs1 O2 169.32(6) 4_564 6_655 ?
O1 Cs1 O2 68.58(4) 3_646 6_655 ?
O2 Cs1 O1 69.18(4) 4_564 5_666 ?
O1 Cs1 O1 83.32(4) 3_646 5_666 ?
O2 Cs1 O1 119.50(4) 6_655 5_666 ?
O2 Cs1 S1 103.21(3) 4_564 7_565 ?
O1 Cs1 S1 115.35(3) 3_646 7_565 ?
O2 Cs1 S1 75.87(3) 6_655 7_565 ?
O1 Cs1 S1 69.70(3) 5_666 7_565 ?
O2 Cs1 S2 89.84(3) 4_564 . ?
O1 Cs1 S2 104.60(3) 3_646 . ?
O2 Cs1 S2 81.87(3) 6_655 . ?
O1 Cs1 S2 158.54(3) 5_666 . ?
S1 Cs1 S2 121.807(13) 7_565 . ?
O2 Cs1 S1 81.97(3) 4_564 . ?
O1 Cs1 S1 67.85(3) 3_646 . ?
O2 Cs1 S1 97.42(3) 6_655 . ?
O1 Cs1 S1 120.33(3) 5_666 . ?
S1 Cs1 S1 169.973(17) 7_565 . ?
S2 Cs1 S1 48.990(12) . . ?
O2 Cs1 S2 76.65(3) 4_564 7_565 ?
O1 Cs1 S2 160.31(2) 3_646 7_565 ?
O2 Cs1 S2 95.68(3) 6_655 7_565 ?
O1 Cs1 S2 95.16(3) 5_666 7_565 ?
S1 Cs1 S2 46.874(11) 7_565 7_565 ?
S2 Cs1 S2 83.891(13) . 7_565 ?
S1 Cs1 S2 128.017(12) . 7_565 ?
C1 S1 Cs1 101.18(7) . 7_566 ?
C1 S1 Cs1 85.61(7) . . ?
Cs1 S1 Cs1 72.905(10) 7_566 . ?
C1 S2 Cs1 89.26(7) . . ?
C1 S2 Cs1 84.95(7) . 7_566 ?
Cs1 S2 Cs1 68.694(10) . 7_566 ?
C3 O1 Cs1 116.57(11) . 3_656 ?
C3 O1 Cs1 97.78(11) . 5_666 ?
Cs1 O1 Cs1 83.26(4) 3_656 5_666 ?
C3 O1 H1O 109.5 . . ?
C5 O2 H2O 109.5 . . ?
C1 N1 C4 123.53(16) . . ?
C1 N1 C2 122.27(16) . . ?
C4 N1 C2 114.20(16) . . ?
N1 C1 S1 120.17(15) . . ?
N1 C1 S2 120.47(15) . . ?
S1 C1 S2 119.34(12) . . ?
N1 C2 C3 111.39(15) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C2 110.93(16) . . ?
O1 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C5 112.21(16) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 C4 111.30(16) . . ?
O2 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
O2 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?

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
C4 N1 C1 S1 174.10(14) . . . . ?
C2 N1 C1 S1 -7.1(2) . . . . ?
C4 N1 C1 S2 -7.6(2) . . . . ?
C2 N1 C1 S2 171.16(14) . . . . ?
C1 N1 C2 C3 95.6(2) . . . . ?
C4 N1 C2 C3 -85.5(2) . . . . ?
N1 C2 C3 O1 -179.84(16) . . . . ?
C1 N1 C4 C5 93.6(2) . . . . ?
C2 N1 C4 C5 -85.3(2) . . . . ?
N1 C4 C5 O2 151.85(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
# '1/2-x, 1/2+y, z'
O1 H1O S2 0.84 2.45 3.2247(17) 154 6_665 ?
O2 H2O S1 0.84 2.34 3.1724(16) 169 8_557 ?
# 'x-1/2, y, 3/2-z'

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.92 # 1.60 A from H3B
_refine_diff_density_min         -0.61 # 0.80 A from CS1
_refine_diff_density_rms         0.096


