# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Hugo Tlahuext'
_publ_contact_author_email       TLAHUEXT@CIQ.UAEM.MX

_publ_section_title              
;
Comparative Analysis of M-O, M-S and Cation-pi(arene)
Interactions in the Alkali Metal (Na+, K+, Rb+, Cs+) Bis-dithiocarbamate
Salts of N,N'-Dibenzyl-1,2-ethylenediamine
;
loop_
_publ_author_name
'Hugo Tlahuext'
'Carolina Godoy-Alcantar'
'Herbert Hopfl'
'Felipe Medrano'
'Reyna Reyes-Martinez'

# Attachment 'revised_file_Compound_1.cif'

data_reyna1m
_database_code_depnum_ccdc_archive 'CCDC 721768'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 S4, H16 Na2 O8'
_chemical_formula_sum            'C18 H34 N2 Na2 O8 S4'
_chemical_formula_weight         580.69

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'
Na Na 0.0362 0.0249 '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

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

_cell_length_a                   6.774(3)
_cell_length_b                   8.264(3)
_cell_length_c                   12.751(5)
_cell_angle_alpha                103.055(9)
_cell_angle_beta                 91.660(9)
_cell_angle_gamma                90.889(10)
_cell_volume                     695.0(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    291
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      17.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             306
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8751
_exptl_absorpt_correction_T_max  0.9178
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3523
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.1319
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2415
_reflns_number_gt                1531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.All O-H hydrogen atoms have
been localized by difference Fourier maps. Since during the unrestricted
refinement of their coordinates the bond distances and bond angles started
to deviate significantly from the expected geometries, the bonding geometries
of the water molecules have been restrained during the refinement using DFIX
and DANG instructions (Ow-H = 0.840(1) Å, Hw...Hw 1.35(1) Å and Na...Hw =
2.73(1) and 2.87(1) Å for the terminal and bridging water molecules,
respectively). The hydrogen atoms of one of the metal-coordinated water
molecules (O3) are disordered over three positions (occ: 0.50, 0.75 and 0.75).
These hydrogen atoms are involved either in (Na)Ow-H...Ow(Na) or Ow-H...S
interactions.
;

_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)+(0.0390P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2415
_refine_ls_number_parameters     181
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.0126(4) 0.8778(3) 0.0958(2) 0.0521(8) Uani 1 1 d D . .
S1 S 0.5688(3) 0.4196(2) 0.15103(15) 0.0501(6) Uani 1 1 d D . .
S2 S 0.2342(3) 0.3776(2) 0.29004(15) 0.0468(5) Uani 1 1 d D . .
N1 N 0.5704(7) 0.5317(6) 0.3643(4) 0.0316(13) Uani 1 1 d . . .
O1 O -0.3235(7) 0.7758(6) 0.0726(4) 0.0609(15) Uani 1 1 d D . .
H11 H -0.368(4) 0.746(7) 0.0088(7) 0.091 Uiso 1 1 d D . .
H12 H -0.351(3) 0.699(6) 0.103(4) 0.091 Uiso 1 1 d D . .
O2 O 0.3348(8) 0.9866(6) 0.1230(5) 0.0792(19) Uani 1 1 d D . .
H21 H 0.4142(16) 0.9082(13) 0.117(6) 0.119 Uiso 1 1 d D . .
H22 H 0.349(3) 1.044(7) 0.186(2) 0.119 Uiso 1 1 d D . .
O3 O 0.1094(8) 0.6064(6) 0.0967(4) 0.084(2) Uani 1 1 d D . .
H31 H 0.056(4) 0.5396(13) 0.0437(16) 0.126 Uiso 0.50 1 d PD . .
H32 H 0.2325(10) 0.596(2) 0.095(2) 0.126 Uiso 0.75 1 d PD . .
H33 H 0.078(4) 0.579(2) 0.1538(13) 0.126 Uiso 0.75 1 d PD . .
O4 O -0.0508(7) 1.1634(6) 0.0942(4) 0.0535(14) Uani 1 1 d D . .
H41 H -0.1697(12) 1.191(2) 0.099(5) 0.080 Uiso 1 1 d D . .
H42 H 0.013(7) 1.2337(13) 0.141(3) 0.080 Uiso 1 1 d D . .
C1 C 0.4708(9) 0.4510(7) 0.2756(5) 0.0313(15) Uani 1 1 d . . .
C2 C 0.4860(10) 0.5700(7) 0.4713(5) 0.0346(16) Uani 1 1 d . . .
H2A H 0.3461 0.5900 0.4642 0.042 Uiso 1 1 calc R . .
H2B H 0.5486 0.6707 0.5141 0.042 Uiso 1 1 calc R . .
C3 C 0.7719(9) 0.5886(7) 0.3606(6) 0.0395(17) Uani 1 1 d . . .
H3A H 0.8321 0.5213 0.2979 0.047 Uiso 1 1 calc R . .
H3B H 0.8447 0.5722 0.4239 0.047 Uiso 1 1 calc R . .
C4 C 0.7907(10) 0.7706(7) 0.3561(5) 0.0349(16) Uani 1 1 d . . .
C5 C 0.6314(10) 0.8706(7) 0.3496(5) 0.0427(18) Uani 1 1 d . . .
H5 H 0.5038 0.8266 0.3479 0.051 Uiso 1 1 calc R . .
C6 C 0.6589(12) 1.0339(8) 0.3457(6) 0.053(2) Uani 1 1 d . . .
H6 H 0.5498 1.0985 0.3397 0.063 Uiso 1 1 calc R . .
C7 C 0.8475(13) 1.1038(9) 0.3506(6) 0.057(2) Uani 1 1 d . . .
H7 H 0.8649 1.2154 0.3501 0.069 Uiso 1 1 calc R . .
C8 C 1.0106(12) 1.0051(9) 0.3564(6) 0.062(2) Uani 1 1 d . . .
H8 H 1.1379 1.0499 0.3582 0.075 Uiso 1 1 calc R . .
C9 C 0.9817(10) 0.8394(9) 0.3594(6) 0.050(2) Uani 1 1 d . . .
H9 H 1.0903 0.7735 0.3636 0.061 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O2 2.334(6) . ?
Na1 O3 2.349(5) . ?
Na1 O4 2.391(6) 2_575 ?
Na1 O1 2.402(6) . ?
Na1 O4 2.410(5) . ?
S1 C1 1.707(6) . ?
S2 C1 1.734(6) . ?
N1 C1 1.334(7) . ?
N1 C3 1.442(7) . ?
N1 C2 1.464(7) . ?
O4 Na1 2.391(6) 2_575 ?
C2 C2 1.515(10) 2_666 ?
C3 C4 1.522(8) . ?
C4 C5 1.381(9) . ?
C4 C9 1.401(8) . ?
C5 C6 1.372(8) . ?
C6 C7 1.388(10) . ?
C7 C8 1.393(10) . ?
C8 C9 1.390(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Na1 O3 93.6(2) . . ?
O2 Na1 O4 89.0(2) . 2_575 ?
O3 Na1 O4 92.7(2) . 2_575 ?
O2 Na1 O1 177.7(2) . . ?
O3 Na1 O1 88.1(2) . . ?
O4 Na1 O1 92.37(18) 2_575 . ?
O2 Na1 O4 80.48(18) . . ?
O3 Na1 O4 174.0(2) . . ?
O4 Na1 O4 86.18(18) 2_575 . ?
O1 Na1 O4 97.75(19) . . ?
C1 N1 C3 121.6(6) . . ?
C1 N1 C2 123.4(5) . . ?
C3 N1 C2 115.0(5) . . ?
Na1 O4 Na1 93.82(18) 2_575 . ?
N1 C1 S1 122.1(5) . . ?
N1 C1 S2 117.8(5) . . ?
S1 C1 S2 120.1(4) . . ?
N1 C2 C2 111.8(6) . 2_666 ?
N1 C3 C4 113.5(5) . . ?
C5 C4 C9 118.7(6) . . ?
C5 C4 C3 123.9(6) . . ?
C9 C4 C3 117.4(6) . . ?
C6 C5 C4 120.9(7) . . ?
C5 C6 C7 120.8(7) . . ?
C6 C7 C8 119.4(6) . . ?
C9 C8 C7 119.5(7) . . ?
C8 C9 C4 120.7(7) . . ?

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 Na1 O4 Na1 89.6(2) . . . 2_575 ?
O4 Na1 O4 Na1 0.0 2_575 . . 2_575 ?
O1 Na1 O4 Na1 -91.88(19) . . . 2_575 ?
C3 N1 C1 S1 -3.8(8) . . . . ?
C2 N1 C1 S1 175.9(4) . . . . ?
C3 N1 C1 S2 176.4(4) . . . . ?
C2 N1 C1 S2 -3.9(7) . . . . ?
C1 N1 C2 C2 88.1(8) . . . 2_666 ?
C3 N1 C2 C2 -92.3(7) . . . 2_666 ?
C1 N1 C3 C4 97.4(7) . . . . ?
C2 N1 C3 C4 -82.3(7) . . . . ?
N1 C3 C4 C5 -3.6(9) . . . . ?
N1 C3 C4 C9 176.0(6) . . . . ?
C9 C4 C5 C6 0.5(11) . . . . ?
C3 C4 C5 C6 -180.0(6) . . . . ?
C4 C5 C6 C7 -1.5(11) . . . . ?
C5 C6 C7 C8 1.9(12) . . . . ?
C6 C7 C8 C9 -1.3(12) . . . . ?
C7 C8 C9 C4 0.3(12) . . . . ?
C5 C4 C9 C8 0.1(11) . . . . ?
C3 C4 C9 C8 -179.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.073

# Attachment 'revised_file_Compound_2.cif'

data_ebdtckm
_database_code_depnum_ccdc_archive 'CCDC 721769'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 K2 N2 O4 S4'
_chemical_formula_sum            'C18 H26 K2 N2 O4 S4'
_chemical_formula_weight         540.85

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.4276(10)
_cell_length_b                   8.0682(12)
_cell_length_c                   12.1202(19)
_cell_angle_alpha                101.826(2)
_cell_angle_beta                 104.093(3)
_cell_angle_gamma                92.107(3)
_cell_volume                     594.19(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2699
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             282
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7618
_exptl_absorpt_correction_T_max  0.9263
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3046
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1992
_reflns_number_gt                1883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. All O-H hydrogen atoms have
been localized by difference Fourier maps. Since during the unrestricted
refinement of their coordinates the bond distances and bond angles started
to deviate significantly from the expected geometries, the bonding
geometries of the water molecules have been restrained during the
refinement using DFIX and DANG instructions (Ow-H = 0.840(1) Å, Hw...Hw =
1.35(1) Å).
;

_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)+(0.0447P)²+0.5987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1992
_refine_ls_number_parameters     148
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.119
_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 0.41628(9) 0.81719(7) 0.58982(5) 0.01687(18) Uani 1 1 d . . .
S1 S 0.62511(10) 0.47140(8) 0.63980(6) 0.01494(19) Uani 1 1 d . . .
S2 S 1.06578(10) 0.37700(8) 0.74177(6) 0.01449(19) Uani 1 1 d . . .
N1 N 0.8217(3) 0.5490(3) 0.86456(18) 0.0104(4) Uani 1 1 d . . .
O1 O -0.0228(3) 0.7053(2) 0.53975(17) 0.0204(4) Uani 1 1 d D . .
H11 H -0.089(4) 0.636(3) 0.565(2) 0.031 Uiso 1 1 d D . .
H12 H -0.051(5) 0.671(3) 0.4670(4) 0.031 Uiso 1 1 d D . .
O2 O 0.2223(3) 0.9941(2) 0.43423(17) 0.0200(4) Uani 1 1 d D . .
H21 H 0.153(4) 0.911(2) 0.383(2) 0.030 Uiso 1 1 d D . .
H22 H 0.144(4) 1.075(2) 0.435(3) 0.030 Uiso 1 1 d D . .
C1 C 0.8368(4) 0.4713(3) 0.7573(2) 0.0118(5) Uani 1 1 d . . .
C2 C 1.0024(4) 0.5727(3) 0.9680(2) 0.0133(5) Uani 1 1 d . . .
H2A H 0.9968 0.6821 1.0215 0.016 Uiso 1 1 calc R . .
H2B H 1.1392 0.5780 0.9445 0.016 Uiso 1 1 calc R . .
C3 C 0.6226(4) 0.6157(3) 0.8852(2) 0.0119(5) Uani 1 1 d . . .
H3A H 0.6221 0.6173 0.9670 0.014 Uiso 1 1 calc R . .
H3B H 0.4993 0.5365 0.8343 0.014 Uiso 1 1 calc R . .
C4 C 0.5884(4) 0.7918(3) 0.8637(2) 0.0117(5) Uani 1 1 d . . .
C5 C 0.7509(4) 0.8983(3) 0.8506(2) 0.0128(5) Uani 1 1 d . . .
H5 H 0.9001 0.8618 0.8605 0.015 Uiso 1 1 calc R . .
C6 C 0.7114(4) 1.0595(3) 0.8306(2) 0.0151(6) Uani 1 1 d . . .
H6 H 0.8329 1.1380 0.8276 0.018 Uiso 1 1 calc R . .
C7 C 0.5100(4) 1.1176(3) 0.8255(2) 0.0173(6) Uani 1 1 d . . .
H7 H 0.4867 1.2378 0.8199 0.021 Uiso 1 1 calc R . .
C8 C 0.3462(4) 1.0124(3) 0.8388(2) 0.0185(6) Uani 1 1 d . . .
H8 H 0.2045 1.0570 0.8428 0.022 Uiso 1 1 calc R . .
C9 C 0.3856(4) 0.8507(3) 0.8575(2) 0.0153(6) Uani 1 1 d . . .
H9 H 0.2705 0.7797 0.8737 0.018 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O2 2.690(2) . ?
K1 O1 2.811(2) . ?
K1 O2 2.838(2) 2_676 ?
K1 S1 3.1898(9) 2_666 ?
K1 S1 3.2441(10) . ?
K1 C8 3.249(3) . ?
K1 C9 3.255(3) . ?
K1 C7 3.258(3) . ?
K1 C6 3.261(3) . ?
K1 C5 3.284(3) . ?
K1 C4 3.286(3) . ?
S1 C1 1.714(3) . ?
S2 C1 1.714(3) . ?
N1 C1 1.351(3) . ?
N1 C2 1.460(3) . ?
N1 C3 1.463(3) . ?
C2 C2 1.537(5) 2_767 ?
C3 C4 1.510(3) . ?
C4 C5 1.388(4) . ?
C4 C9 1.394(3) . ?
C5 C6 1.392(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.391(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 K1 O1 76.00(6) . . ?
O2 K1 O2 79.23(6) . 2_676 ?
O1 K1 O2 155.19(6) . 2_676 ?
O2 K1 S1 82.56(5) . 2_666 ?
O1 K1 S1 80.14(4) . 2_666 ?
O2 K1 S1 95.41(4) 2_676 2_666 ?
O2 K1 S1 148.63(5) . . ?
O1 K1 S1 99.48(5) . . ?
O2 K1 S1 100.94(4) 2_676 . ?
S1 K1 S1 66.13(2) 2_666 . ?
O2 K1 C8 105.60(7) . . ?
O1 K1 C8 84.17(6) . . ?
O2 K1 C8 103.96(6) 2_676 . ?
S1 K1 C8 160.02(5) 2_666 . ?
S1 K1 C8 104.76(5) . . ?
O2 K1 C9 128.19(7) . . ?
O1 K1 C9 82.47(6) . . ?
O2 K1 C9 114.63(6) 2_676 . ?
S1 K1 C9 139.05(5) 2_666 . ?
S1 K1 C9 80.72(5) . . ?
C8 K1 C9 24.70(7) . . ?
O2 K1 C7 98.89(7) . . ?
O1 K1 C7 105.64(6) . . ?
O2 K1 C7 79.42(6) 2_676 . ?
S1 K1 C7 174.22(5) 2_666 . ?
S1 K1 C7 112.07(5) . . ?
C8 K1 C7 24.64(7) . . ?
C9 K1 C7 43.37(7) . . ?
O2 K1 C6 113.01(7) . . ?
O1 K1 C6 127.30(6) . . ?
O2 K1 C6 64.73(6) 2_676 . ?
S1 K1 C6 150.09(5) 2_666 . ?
S1 K1 C6 94.61(5) . . ?
C8 K1 C6 43.14(7) . . ?
C9 K1 C6 50.16(7) . . ?
C7 K1 C6 24.52(7) . . ?
O2 K1 C5 137.52(6) . . ?
O1 K1 C5 124.92(6) . . ?
O2 K1 C5 75.62(6) 2_676 . ?
S1 K1 C5 133.11(5) 2_666 . ?
S1 K1 C5 70.60(5) . . ?
C8 K1 C5 50.21(7) . . ?
C9 K1 C5 42.87(6) . . ?
C7 K1 C5 43.25(6) . . ?
C6 K1 C5 24.56(6) . . ?
O2 K1 C4 148.48(6) . . ?
O1 K1 C4 101.89(6) . . ?
O2 K1 C4 99.89(6) 2_676 . ?
S1 K1 C4 128.55(5) 2_666 . ?
S1 K1 C4 62.83(4) . . ?
C8 K1 C4 43.56(7) . . ?
C9 K1 C4 24.62(6) . . ?
C7 K1 C4 50.74(7) . . ?
C6 K1 C4 43.31(6) . . ?
C5 K1 C4 24.39(6) . . ?
C1 S1 K1 117.38(9) . 2_666 ?
C1 S1 K1 122.41(8) . . ?
K1 S1 K1 113.87(2) 2_666 . ?
C1 N1 C2 122.5(2) . . ?
C1 N1 C3 122.2(2) . . ?
C2 N1 C3 115.3(2) . . ?
K1 O2 K1 100.77(6) . 2_676 ?
N1 C1 S1 118.60(19) . . ?
N1 C1 S2 119.62(19) . . ?
S1 C1 S2 121.78(15) . . ?
N1 C2 C2 111.6(2) . 2_767 ?
N1 C3 C4 115.2(2) . . ?
C5 C4 C9 118.4(2) . . ?
C5 C4 C3 122.8(2) . . ?
C9 C4 C3 118.8(2) . . ?
C5 C4 K1 77.74(15) . . ?
C9 C4 K1 76.45(15) . . ?
C3 C4 K1 116.16(15) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 K1 77.87(15) . . ?
C6 C5 K1 76.79(15) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 K1 77.63(15) . . ?
C5 C6 K1 78.65(14) . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 K1 77.85(15) . . ?
C8 C7 K1 77.32(16) . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 K1 78.04(16) . . ?
C9 C8 K1 77.87(15) . . ?
C8 C9 C4 121.1(2) . . ?
C8 C9 K1 77.43(16) . . ?
C4 C9 K1 78.93(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 K1 S1 C1 147.32(13) . . . . ?
O1 K1 S1 C1 -134.06(11) . . . . ?
O2 K1 S1 C1 60.11(11) 2_676 . . . ?
S1 K1 S1 C1 151.23(11) 2_666 . . . ?
C8 K1 S1 C1 -47.64(11) . . . . ?
C9 K1 S1 C1 -53.38(11) . . . . ?
C7 K1 S1 C1 -22.80(12) . . . . ?
C6 K1 S1 C1 -5.02(11) . . . . ?
C5 K1 S1 C1 -10.25(11) . . . . ?
C4 K1 S1 C1 -35.48(11) . . . . ?
K1 K1 S1 C1 86.22(11) 2_676 . . . ?
O2 K1 S1 K1 -3.91(9) . . . 2_666 ?
O1 K1 S1 K1 74.71(5) . . . 2_666 ?
O2 K1 S1 K1 -91.12(5) 2_676 . . 2_666 ?
S1 K1 S1 K1 0.0 2_666 . . 2_666 ?
C8 K1 S1 K1 161.13(5) . . . 2_666 ?
C9 K1 S1 K1 155.39(5) . . . 2_666 ?
C7 K1 S1 K1 -174.03(6) . . . 2_666 ?
C6 K1 S1 K1 -156.25(5) . . . 2_666 ?
C5 K1 S1 K1 -161.48(5) . . . 2_666 ?
C4 K1 S1 K1 173.29(5) . . . 2_666 ?
K1 K1 S1 K1 -65.01(4) 2_676 . . 2_666 ?
O1 K1 O2 K1 -178.63(7) . . . 2_676 ?
O2 K1 O2 K1 0.0 2_676 . . 2_676 ?
S1 K1 O2 K1 -96.99(5) 2_666 . . 2_676 ?
S1 K1 O2 K1 -93.38(9) . . . 2_676 ?
C8 K1 O2 K1 101.64(7) . . . 2_676 ?
C9 K1 O2 K1 112.97(8) . . . 2_676 ?
C7 K1 O2 K1 77.36(7) . . . 2_676 ?
C6 K1 O2 K1 56.43(8) . . . 2_676 ?
C5 K1 O2 K1 54.41(11) . . . 2_676 ?
C4 K1 O2 K1 91.39(12) . . . 2_676 ?
C2 N1 C1 S1 -172.76(17) . . . . ?
C3 N1 C1 S1 7.2(3) . . . . ?
C2 N1 C1 S2 6.7(3) . . . . ?
C3 N1 C1 S2 -173.30(17) . . . . ?
K1 S1 C1 N1 -157.79(16) 2_666 . . . ?
K1 S1 C1 N1 51.9(2) . . . . ?
K1 S1 C1 S2 22.72(18) 2_666 . . . ?
K1 S1 C1 S2 -127.57(12) . . . . ?
C1 N1 C2 C2 -93.6(3) . . . 2_767 ?
C3 N1 C2 C2 86.4(3) . . . 2_767 ?
C1 N1 C3 C4 -84.1(3) . . . . ?
C2 N1 C3 C4 95.8(3) . . . . ?
N1 C3 C4 C5 -13.6(3) . . . . ?
N1 C3 C4 C9 166.8(2) . . . . ?
N1 C3 C4 K1 78.4(2) . . . . ?
O2 K1 C4 C5 -79.62(19) . . . . ?
O1 K1 C4 C5 -162.18(14) . . . . ?
O2 K1 C4 C5 5.87(15) 2_676 . . . ?
S1 K1 C4 C5 111.02(14) 2_666 . . . ?
S1 K1 C4 C5 103.17(15) . . . . ?
C8 K1 C4 C5 -94.03(17) . . . . ?
C9 K1 C4 C5 -123.6(2) . . . . ?
C7 K1 C4 C5 -61.60(15) . . . . ?
C6 K1 C4 C5 -29.38(14) . . . . ?
K1 K1 C4 C5 -19.88(17) 2_676 . . . ?
O2 K1 C4 C9 43.9(2) . . . . ?
O1 K1 C4 C9 -38.62(15) . . . . ?
O2 K1 C4 C9 129.44(15) 2_676 . . . ?
S1 K1 C4 C9 -125.41(14) 2_666 . . . ?
S1 K1 C4 C9 -133.27(15) . . . . ?
C8 K1 C4 C9 29.54(14) . . . . ?
C7 K1 C4 C9 61.96(15) . . . . ?
C6 K1 C4 C9 94.18(16) . . . . ?
C5 K1 C4 C9 123.6(2) . . . . ?
K1 K1 C4 C9 103.68(14) 2_676 . . . ?
O2 K1 C4 C3 159.65(15) . . . . ?
O1 K1 C4 C3 77.09(17) . . . . ?
O2 K1 C4 C3 -114.85(16) 2_676 . . . ?
S1 K1 C4 C3 -9.71(19) 2_666 . . . ?
S1 K1 C4 C3 -17.56(14) . . . . ?
C8 K1 C4 C3 145.2(2) . . . . ?
C9 K1 C4 C3 115.7(2) . . . . ?
C7 K1 C4 C3 177.7(2) . . . . ?
C6 K1 C4 C3 -150.1(2) . . . . ?
C5 K1 C4 C3 -120.7(2) . . . . ?
K1 K1 C4 C3 -140.61(14) 2_676 . . . ?
C9 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 C6 179.8(2) . . . . ?
K1 C4 C5 C6 66.5(2) . . . . ?
C9 C4 C5 K1 -67.0(2) . . . . ?
C3 C4 C5 K1 113.4(2) . . . . ?
O2 K1 C5 C4 130.42(15) . . . . ?
O1 K1 C5 C4 21.42(17) . . . . ?
O2 K1 C5 C4 -174.03(16) 2_676 . . . ?
S1 K1 C5 C4 -90.14(15) 2_666 . . . ?
S1 K1 C5 C4 -66.69(14) . . . . ?
C8 K1 C5 C4 63.46(15) . . . . ?
C9 K1 C5 C4 30.67(14) . . . . ?
C7 K1 C5 C4 96.21(17) . . . . ?
C6 K1 C5 C4 125.9(2) . . . . ?
K1 K1 C5 C4 164.33(14) 2_676 . . . ?
O2 K1 C5 C6 4.49(19) . . . . ?
O1 K1 C5 C6 -104.51(15) . . . . ?
O2 K1 C5 C6 60.04(15) 2_676 . . . ?
S1 K1 C5 C6 143.93(13) 2_666 . . . ?
S1 K1 C5 C6 167.38(15) . . . . ?
C8 K1 C5 C6 -62.47(15) . . . . ?
C9 K1 C5 C6 -95.26(17) . . . . ?
C7 K1 C5 C6 -29.72(14) . . . . ?
C4 K1 C5 C6 -125.9(2) . . . . ?
K1 K1 C5 C6 38.40(15) 2_676 . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
K1 C5 C6 C7 68.2(2) . . . . ?
C4 C5 C6 K1 -67.0(2) . . . . ?
O2 K1 C6 C7 58.22(17) . . . . ?
O1 K1 C6 C7 -31.38(18) . . . . ?
O2 K1 C6 C7 123.07(17) 2_676 . . . ?
S1 K1 C6 C7 175.38(13) 2_666 . . . ?
S1 K1 C6 C7 -137.00(15) . . . . ?
C8 K1 C6 C7 -30.28(15) . . . . ?
C9 K1 C6 C7 -63.13(16) . . . . ?
C5 K1 C6 C7 -125.1(2) . . . . ?
C4 K1 C6 C7 -95.89(17) . . . . ?
K1 K1 C6 C7 91.30(15) 2_676 . . . ?
O2 K1 C6 C5 -176.71(14) . . . . ?
O1 K1 C6 C5 93.68(16) . . . . ?
O2 K1 C6 C5 -111.86(16) 2_676 . . . ?
S1 K1 C6 C5 -59.56(19) 2_666 . . . ?
S1 K1 C6 C5 -11.93(15) . . . . ?
C8 K1 C6 C5 94.78(17) . . . . ?
C9 K1 C6 C5 61.93(15) . . . . ?
C7 K1 C6 C5 125.1(2) . . . . ?
C4 K1 C6 C5 29.18(14) . . . . ?
K1 K1 C6 C5 -143.64(15) 2_676 . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
K1 C6 C7 C8 67.8(2) . . . . ?
C5 C6 C7 K1 -68.7(2) . . . . ?
O2 K1 C7 C6 -127.63(15) . . . . ?
O1 K1 C7 C6 154.52(15) . . . . ?
O2 K1 C7 C6 -50.43(15) 2_676 . . . ?
S1 K1 C7 C6 47.18(16) . . . . ?
C8 K1 C7 C6 124.2(2) . . . . ?
C9 K1 C7 C6 94.16(18) . . . . ?
C5 K1 C7 C6 29.77(14) . . . . ?
C4 K1 C7 C6 61.79(15) . . . . ?
K1 K1 C7 C6 -87.93(15) 2_676 . . . ?
O2 K1 C7 C8 108.16(17) . . . . ?
O1 K1 C7 C8 30.31(18) . . . . ?
O2 K1 C7 C8 -174.64(17) 2_676 . . . ?
S1 K1 C7 C8 -77.02(17) . . . . ?
C9 K1 C7 C8 -30.05(15) . . . . ?
C6 K1 C7 C8 -124.2(2) . . . . ?
C5 K1 C7 C8 -94.44(18) . . . . ?
C4 K1 C7 C8 -62.42(16) . . . . ?
K1 K1 C7 C8 147.87(16) 2_676 . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
K1 C7 C8 C9 68.3(2) . . . . ?
C6 C7 C8 K1 -68.0(2) . . . . ?
O2 K1 C8 C7 -77.07(17) . . . . ?
O1 K1 C8 C7 -150.75(17) . . . . ?
O2 K1 C8 C7 5.43(17) 2_676 . . . ?
S1 K1 C8 C7 170.94(14) 2_666 . . . ?
S1 K1 C8 C7 110.95(16) . . . . ?
C9 K1 C8 C7 124.6(2) . . . . ?
C6 K1 C8 C7 30.13(15) . . . . ?
C5 K1 C8 C7 62.75(16) . . . . ?
C4 K1 C8 C7 95.17(18) . . . . ?
K1 K1 C8 C7 -34.29(17) 2_676 . . . ?
O2 K1 C8 C9 158.32(15) . . . . ?
O1 K1 C8 C9 84.64(15) . . . . ?
O2 K1 C8 C9 -119.18(15) 2_676 . . . ?
S1 K1 C8 C9 46.3(3) 2_666 . . . ?
S1 K1 C8 C9 -13.66(16) . . . . ?
C7 K1 C8 C9 -124.6(2) . . . . ?
C6 K1 C8 C9 -94.48(18) . . . . ?
C5 K1 C8 C9 -61.86(15) . . . . ?
C4 K1 C8 C9 -29.44(14) . . . . ?
K1 K1 C8 C9 -158.90(14) 2_676 . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
K1 C8 C9 C4 68.7(2) . . . . ?
C7 C8 C9 K1 -68.4(2) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C3 C4 C9 C8 179.5(2) . . . . ?
K1 C4 C9 C8 -67.9(2) . . . . ?
C5 C4 C9 K1 67.8(2) . . . . ?
C3 C4 C9 K1 -112.6(2) . . . . ?
O2 K1 C9 C8 -26.91(18) . . . . ?
O1 K1 C9 C8 -92.43(16) . . . . ?
O2 K1 C9 C8 68.78(16) 2_676 . . . ?
S1 K1 C9 C8 -157.85(13) 2_666 . . . ?
S1 K1 C9 C8 166.63(16) . . . . ?
C7 K1 C9 C8 29.98(15) . . . . ?
C6 K1 C9 C8 62.60(16) . . . . ?
C5 K1 C9 C8 95.22(17) . . . . ?
C4 K1 C9 C8 125.6(2) . . . . ?
K1 K1 C9 C8 27.18(18) 2_676 . . . ?
O2 K1 C9 C4 -152.51(13) . . . . ?
O1 K1 C9 C4 141.97(15) . . . . ?
O2 K1 C9 C4 -56.83(16) 2_676 . . . ?
S1 K1 C9 C4 76.55(16) 2_666 . . . ?
S1 K1 C9 C4 41.02(14) . . . . ?
C8 K1 C9 C4 -125.6(2) . . . . ?
C7 K1 C9 C4 -95.62(17) . . . . ?
C6 K1 C9 C4 -63.00(15) . . . . ?
C5 K1 C9 C4 -30.38(14) . . . . ?
K1 K1 C9 C4 -98.43(15) 2_676 . . . ?

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.949
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.077

# Attachment 'revised_file_Compound_3.cif'

data_3reynam
_database_code_depnum_ccdc_archive 'CCDC 721770'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N2 O Rb2 S4'
_chemical_formula_sum            'C18 H20 N2 O Rb2 S4'
_chemical_formula_weight         579.54

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'
Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   21.895(2)
_cell_length_b                   6.4024(7)
_cell_length_c                   17.4640(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.530(2)
_cell_angle_gamma                90.00
_cell_volume                     2321.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2779
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    4.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.195
_exptl_absorpt_correction_T_max  0.459
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8289
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2051
_reflns_number_gt                1757
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
All O-H hydrogen atoms have been localized by difference Fourier maps.
Since during the unrestricted refinement of their coordinates the bond
distances and bond angles started to deviate significantly from the
expected geometries, the bonding geometries of the water molecules have
been restrained during the refinement using DFIX and DANG instructions
(Ow-H = 0.840(1) Å, Hw...Hw 1.35(1) Å and Rb...Hw = 3.00(1), 3.10(1),
3.40(1) and 3.55(1) Å, respectively).
;

_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)+(0.0426P)²+6.3074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2051
_refine_ls_number_parameters     141
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.234
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1154(3) 0.7108(8) 0.4520(3) 0.0394(13) Uani 1 1 d . . .
C2 C 0.2295(3) 0.7184(9) 0.4584(3) 0.0448(14) Uani 1 1 d . . .
H2A H 0.2499 0.7640 0.4195 0.054 Uiso 1 1 calc R . .
H2B H 0.2262 0.5673 0.4556 0.054 Uiso 1 1 calc R . .
C3 C 0.1599(3) 1.0164(8) 0.4007(3) 0.0467(14) Uani 1 1 d . . .
H3A H 0.1955 1.1013 0.4330 0.056 Uiso 1 1 calc R . .
H3B H 0.1203 1.0816 0.4020 0.056 Uiso 1 1 calc R . .
C4 C 0.1609(3) 1.0134(9) 0.3146(3) 0.0436(14) Uani 1 1 d . . .
C5 C 0.1385(3) 0.8479(10) 0.2635(4) 0.0558(17) Uani 1 1 d . . .
H5 H 0.1229 0.7293 0.2818 0.067 Uiso 1 1 calc R . .
C6 C 0.1391(3) 0.8575(12) 0.1849(4) 0.0644(19) Uani 1 1 d . . .
H6 H 0.1235 0.7449 0.1506 0.077 Uiso 1 1 calc R . .
C7 C 0.1619(3) 1.0268(13) 0.1566(4) 0.066(2) Uani 1 1 d . . .
H7 H 0.1625 1.0299 0.1036 0.079 Uiso 1 1 calc R . .
C8 C 0.1840(3) 1.1934(12) 0.2067(4) 0.069(2) Uani 1 1 d . . .
H8 H 0.1991 1.3117 0.1876 0.082 Uiso 1 1 calc R . .
C9 C 0.1841(3) 1.1865(10) 0.2853(4) 0.0564(16) Uani 1 1 d . . .
H9 H 0.1999 1.2996 0.3192 0.068 Uiso 1 1 calc R . .
N1 N 0.1648(2) 0.8078(7) 0.4371(3) 0.0420(11) Uani 1 1 d . . .
Rb1 Rb 0.02257(3) 0.68956(10) 0.60242(4) 0.0613(3) Uani 1 1 d D . .
S1 S 0.12887(7) 0.4811(2) 0.50467(10) 0.0478(4) Uani 1 1 d . . .
S2 S 0.03912(7) 0.8151(3) 0.41819(11) 0.0559(4) Uani 1 1 d . . .
O1 O 0.0000 0.4648(19) 0.7500 0.082(4) Uani 0.608(13) 2 d SPD . 1
H11 H -0.029(3) 0.555(10) 0.734(4) 0.124 Uiso 0.304(7) 1 d PD . 1
H12 H -0.018(4) 0.347(6) 0.7389(16) 0.124 Uiso 0.304(7) 1 d PD . 1
O1B O 0.0000 0.872(3) 0.7500 0.085(7) Uani 0.392(13) 2 d SPD . 2
H11B H 0.009(12) 1.000(10) 0.754(9) 0.128 Uiso 0.196(7) 1 d PD . 2
H12B H -0.03975(13) 0.86(4) 0.726(6) 0.128 Uiso 0.196(7) 1 d PD . 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(7) . ?
C1 S1 1.710(6) . ?
C1 S2 1.720(6) . ?
C2 N1 1.461(7) . ?
C2 C2 1.502(11) 7_566 ?
C3 N1 1.468(7) . ?
C3 C4 1.511(8) . ?
C4 C5 1.372(8) . ?
C4 C9 1.384(8) . ?
C5 C6 1.377(9) . ?
C6 C7 1.352(9) . ?
C7 C8 1.368(10) . ?
C7 Rb1 3.415(7) 6_575 ?
C8 C9 1.372(9) . ?
C8 Rb1 3.505(7) 6_575 ?
Rb1 O1B 3.011(8) . ?
Rb1 O1 3.125(6) . ?
Rb1 S2 3.4209(17) 5_576 ?
Rb1 S1 3.4269(17) 5_566 ?
Rb1 S2 3.4452(18) . ?
Rb1 S2 3.4763(18) 5_566 ?
Rb1 S1 3.5550(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S1 119.3(4) . . ?
N1 C1 S2 120.5(4) . . ?
S1 C1 S2 120.1(3) . . ?
N1 C2 C2 112.0(5) . 7_566 ?
N1 C3 C4 113.4(4) . . ?
C5 C4 C9 118.4(6) . . ?
C5 C4 C3 122.9(5) . . ?
C9 C4 C3 118.7(5) . . ?
C4 C5 C6 120.0(6) . . ?
C7 C6 C5 121.5(7) . . ?
C6 C7 C8 119.2(6) . . ?
C6 C7 Rb1 97.3(4) . 6_575 ?
C8 C7 Rb1 82.3(4) . 6_575 ?
C7 C8 C9 120.2(6) . . ?
C7 C8 Rb1 74.9(4) . 6_575 ?
C9 C8 Rb1 101.9(4) . 6_575 ?
C8 C9 C4 120.8(6) . . ?
C1 N1 C2 123.0(5) . . ?
C1 N1 C3 123.6(5) . . ?
C2 N1 C3 113.4(4) . . ?
O1B Rb1 O1 50.3(4) . . ?
O1B Rb1 C7 86.1(2) . 6_576 ?
O1 Rb1 C7 112.20(15) . 6_576 ?
O1B Rb1 S2 64.1(3) . 5_576 ?
O1 Rb1 S2 110.67(19) . 5_576 ?
C7 Rb1 S2 79.87(14) 6_576 5_576 ?
O1B Rb1 S1 101.39(10) . 5_566 ?
O1 Rb1 S1 85.65(7) . 5_566 ?
C7 Rb1 S1 160.87(14) 6_576 5_566 ?
S2 Rb1 S1 87.53(4) 5_576 5_566 ?
O1B Rb1 S2 143.5(3) . . ?
O1 Rb1 S2 165.6(2) . . ?
C7 Rb1 S2 77.57(12) 6_576 . ?
S2 Rb1 S2 80.83(5) 5_576 . ?
S1 Rb1 S2 86.30(4) 5_566 . ?
O1B Rb1 S2 106.6(3) . 5_566 ?
O1 Rb1 S2 59.96(19) . 5_566 ?
C7 Rb1 S2 143.74(14) 6_576 5_566 ?
S2 Rb1 S2 136.33(5) 5_576 5_566 ?
S1 Rb1 S2 50.99(4) 5_566 5_566 ?
S2 Rb1 S2 105.83(4) . 5_566 ?
O1B Rb1 C8 83.38(13) . 6_576 ?
O1 Rb1 C8 93.86(14) . 6_576 ?
C7 Rb1 C8 22.76(16) 6_576 6_576 ?
S2 Rb1 C8 98.96(13) 5_576 6_576 ?
S1 Rb1 C8 173.20(12) 5_566 6_576 ?
S2 Rb1 C8 92.72(13) . 6_576 ?
S2 Rb1 C8 123.16(14) 5_566 6_576 ?
O1B Rb1 S1 150.17(5) . . ?
O1 Rb1 S1 121.49(17) . . ?
C7 Rb1 S1 70.68(12) 6_576 . ?
S2 Rb1 S1 126.47(4) 5_576 . ?
S1 Rb1 S1 106.61(3) 5_566 . ?
S2 Rb1 S1 50.21(4) . . ?
S2 Rb1 S1 83.88(4) 5_566 . ?
C8 Rb1 S1 67.90(11) 6_576 . ?
C1 S1 Rb1 90.51(19) . 5_566 ?
C1 S1 Rb1 84.72(18) . . ?
Rb1 S1 Rb1 73.39(3) 5_566 . ?
C1 S2 Rb1 134.8(2) . 5_576 ?
C1 S2 Rb1 88.15(19) . . ?
Rb1 S2 Rb1 99.17(4) 5_576 . ?
C1 S2 Rb1 88.71(19) . 5_566 ?
Rb1 S2 Rb1 136.33(5) 5_576 5_566 ?
Rb1 S2 Rb1 74.17(4) . 5_566 ?
Rb1 O1 Rb1 125.2(4) 2_556 . ?
Rb1 O1B Rb1 134.3(7) . 2_556 ?

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
N1 C3 C4 C5 29.0(8) . . . . ?
N1 C3 C4 C9 -152.5(5) . . . . ?
C9 C4 C5 C6 -0.4(9) . . . . ?
C3 C4 C5 C6 178.2(6) . . . . ?
C4 C5 C6 C7 0.5(11) . . . . ?
C5 C6 C7 C8 -0.9(11) . . . . ?
C5 C6 C7 Rb1 -86.1(7) . . . 6_575 ?
C6 C7 C8 C9 1.2(11) . . . . ?
Rb1 C7 C8 C9 95.2(7) 6_575 . . . ?
C6 C7 C8 Rb1 -94.1(6) . . . 6_575 ?
C7 C8 C9 C4 -1.1(10) . . . . ?
Rb1 C8 C9 C4 78.3(6) 6_575 . . . ?
C5 C4 C9 C8 0.7(9) . . . . ?
C3 C4 C9 C8 -178.0(6) . . . . ?
S1 C1 N1 C2 5.0(7) . . . . ?
S2 C1 N1 C2 -174.8(4) . . . . ?
S1 C1 N1 C3 -172.8(4) . . . . ?
S2 C1 N1 C3 7.5(7) . . . . ?
C2 C2 N1 C1 -90.4(7) 7_566 . . . ?
C2 C2 N1 C3 87.6(7) 7_566 . . . ?
C4 C3 N1 C1 -107.8(6) . . . . ?
C4 C3 N1 C2 74.2(6) . . . . ?
N1 C1 S1 Rb1 -147.7(4) . . . 5_566 ?
S2 C1 S1 Rb1 32.0(3) . . . 5_566 ?
N1 C1 S1 Rb1 139.0(4) . . . . ?
S2 C1 S1 Rb1 -41.3(3) . . . . ?
O1B Rb1 S1 C1 -108.7(7) . . . . ?
O1 Rb1 S1 C1 -172.7(2) . . . . ?
C7 Rb1 S1 C1 -68.0(2) 6_576 . . . ?
S2 Rb1 S1 C1 -7.4(2) 5_576 . . . ?
S1 Rb1 S1 C1 92.11(19) 5_566 . . . ?
S2 Rb1 S1 C1 21.76(19) . . . . ?
S2 Rb1 S1 C1 138.28(19) 5_566 . . . ?
C8 Rb1 S1 C1 -92.1(2) 6_576 . . . ?
Rb1 Rb1 S1 C1 92.11(19) 5_566 . . . ?
Rb1 Rb1 S1 C1 6.91(19) 5_576 . . . ?
O1B Rb1 S1 Rb1 159.1(7) . . . 5_566 ?
O1 Rb1 S1 Rb1 95.16(14) . . . 5_566 ?
C7 Rb1 S1 Rb1 -160.08(15) 6_576 . . 5_566 ?
S2 Rb1 S1 Rb1 -99.47(5) 5_576 . . 5_566 ?
S1 Rb1 S1 Rb1 0.0 5_566 . . 5_566 ?
S2 Rb1 S1 Rb1 -70.36(5) . . . 5_566 ?
S2 Rb1 S1 Rb1 46.16(3) 5_566 . . 5_566 ?
C8 Rb1 S1 Rb1 175.75(15) 6_576 . . 5_566 ?
Rb1 Rb1 S1 Rb1 -85.20(3) 5_576 . . 5_566 ?
N1 C1 S2 Rb1 -36.5(6) . . . 5_576 ?
S1 C1 S2 Rb1 143.8(2) . . . 5_576 ?
N1 C1 S2 Rb1 -137.6(4) . . . . ?
S1 C1 S2 Rb1 42.7(3) . . . . ?
N1 C1 S2 Rb1 148.2(4) . . . 5_566 ?
S1 C1 S2 Rb1 -31.5(3) . . . 5_566 ?
O1B Rb1 S2 C1 119.0(2) . . . . ?
O1 Rb1 S2 C1 -80.8(3) . . . . ?
C7 Rb1 S2 C1 53.5(2) 6_576 . . . ?
S2 Rb1 S2 C1 135.1(2) 5_576 . . . ?
S1 Rb1 S2 C1 -136.80(19) 5_566 . . . ?
S2 Rb1 S2 C1 -89.18(19) 5_566 . . . ?
C8 Rb1 S2 C1 36.5(2) 6_576 . . . ?
S1 Rb1 S2 C1 -21.54(18) . . . . ?
Rb1 Rb1 S2 C1 -89.18(19) 5_566 . . . ?
Rb1 Rb1 S2 C1 135.1(2) 5_576 . . . ?
O1B Rb1 S2 Rb1 -16.09(10) . . . 5_576 ?
O1 Rb1 S2 Rb1 144.1(2) . . . 5_576 ?
C7 Rb1 S2 Rb1 -81.56(14) 6_576 . . 5_576 ?
S2 Rb1 S2 Rb1 0.0 5_576 . . 5_576 ?
S1 Rb1 S2 Rb1 88.09(4) 5_566 . . 5_576 ?
S2 Rb1 S2 Rb1 135.71(5) 5_566 . . 5_576 ?
C8 Rb1 S2 Rb1 -98.65(13) 6_576 . . 5_576 ?
S1 Rb1 S2 Rb1 -156.65(7) . . . 5_576 ?
Rb1 Rb1 S2 Rb1 135.71(5) 5_566 . . 5_576 ?
O1B Rb1 S2 Rb1 -151.80(8) . . . 5_566 ?
O1 Rb1 S2 Rb1 8.4(3) . . . 5_566 ?
C7 Rb1 S2 Rb1 142.73(14) 6_576 . . 5_566 ?
S2 Rb1 S2 Rb1 -135.71(5) 5_576 . . 5_566 ?
S1 Rb1 S2 Rb1 -47.62(3) 5_566 . . 5_566 ?
S2 Rb1 S2 Rb1 0.0 5_566 . . 5_566 ?
C8 Rb1 S2 Rb1 125.64(13) 6_576 . . 5_566 ?
S1 Rb1 S2 Rb1 67.64(4) . . . 5_566 ?
Rb1 Rb1 S2 Rb1 -135.71(5) 5_576 . . 5_566 ?
O1B Rb1 O1 Rb1 0.000(1) . . . 2_556 ?
C7 Rb1 O1 Rb1 64.19(16) 6_576 . . 2_556 ?
S2 Rb1 O1 Rb1 -23.00(5) 5_576 . . 2_556 ?
S1 Rb1 O1 Rb1 -108.70(3) 5_566 . . 2_556 ?
S2 Rb1 O1 Rb1 -164.8(3) . . . 2_556 ?
S2 Rb1 O1 Rb1 -155.45(6) 5_566 . . 2_556 ?
C8 Rb1 O1 Rb1 78.09(12) 6_576 . . 2_556 ?
S1 Rb1 O1 Rb1 144.46(8) . . . 2_556 ?
Rb1 Rb1 O1 Rb1 -157.52(4) 5_566 . . 2_556 ?
Rb1 Rb1 O1 Rb1 -34.8(2) 5_576 . . 2_556 ?
O1 Rb1 O1B Rb1 0.0 . . . 2_556 ?
C7 Rb1 O1B Rb1 -123.34(14) 6_576 . . 2_556 ?
S2 Rb1 O1B Rb1 156.02(8) 5_576 . . 2_556 ?
S1 Rb1 O1B Rb1 74.46(7) 5_566 . . 2_556 ?
S2 Rb1 O1B Rb1 173.73(8) . . . 2_556 ?
S2 Rb1 O1B Rb1 22.05(5) 5_566 . . 2_556 ?
C8 Rb1 O1B Rb1 -100.64(15) 6_576 . . 2_556 ?
S1 Rb1 O1B Rb1 -85.2(6) . . . 2_556 ?
Rb1 Rb1 O1B Rb1 54.6(6) 5_566 . . 2_556 ?
Rb1 Rb1 O1B Rb1 163.09(4) 5_576 . . 2_556 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.084

# Attachment 'revised_file_Compound_4.cif'

data_dtccs2m
_database_code_depnum_ccdc_archive 'CCDC 721771'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 Cs2 N2 O S4'
_chemical_formula_sum            'C18 H20 Cs2 N2 O S4'
_chemical_formula_weight         674.42

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'
Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   22.4220(19)
_cell_length_b                   6.5428(6)
_cell_length_c                   17.4010(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.7110(10)
_cell_angle_gamma                90.00
_cell_volume                     2387.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9075
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    3.414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3828
_exptl_absorpt_correction_T_max  0.6206
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11021
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2105
_reflns_number_gt                2046
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
All O-H hydrogen atoms have been localized by difference Fourier maps.
Since during the unrestricted refinement of their coordinates the bond
distances and bond angles started to deviate significantly from the
expected geometries, the bonding geometries of the water molecules have
been restrained during the refinement using DFIX and DANG instructions
(Ow-H = 0.840(1) Å, Hw...Hw 1.35(1) Å and Cs...Hw = 3.15(1), 3.25(1),
3.50(1) and 3.65(1) Å, respectively.
;

_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)+(0.0277P)²+5.4038P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2105
_refine_ls_number_parameters     141
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11751(16) 0.7129(5) 0.4516(2) 0.0360(7) Uani 1 1 d . . .
C2 C 0.22858(17) 0.7198(6) 0.4573(2) 0.0433(8) Uani 1 1 d . . .
H2A H 0.2248 0.5721 0.4540 0.052 Uiso 1 1 calc R . .
H2B H 0.2476 0.7642 0.4180 0.052 Uiso 1 1 calc R . .
C3 C 0.1593(2) 1.0130(6) 0.3996(2) 0.0475(9) Uani 1 1 d . . .
H3A H 0.1937 1.0982 0.4344 0.057 Uiso 1 1 calc R . .
H3B H 0.1194 1.0735 0.3979 0.057 Uiso 1 1 calc R . .
C4 C 0.16153(16) 1.0113(6) 0.3137(2) 0.0412(8) Uani 1 1 d . . .
C5 C 0.1366(2) 0.8535(6) 0.2590(3) 0.0527(9) Uani 1 1 d . . .
H5 H 0.1173 0.7434 0.2747 0.063 Uiso 1 1 calc R . .
C6 C 0.1399(2) 0.8574(7) 0.1815(3) 0.0580(10) Uani 1 1 d . . .
H6 H 0.1233 0.7492 0.1456 0.070 Uiso 1 1 calc R . .
C7 C 0.16731(19) 1.0189(7) 0.1569(2) 0.0580(11) Uani 1 1 d . . .
H7 H 0.1689 1.0218 0.1042 0.070 Uiso 1 1 calc R . .
C8 C 0.1925(2) 1.1764(7) 0.2102(3) 0.0630(12) Uani 1 1 d . . .
H8 H 0.2117 1.2859 0.1940 0.076 Uiso 1 1 calc R . .
C9 C 0.1894(2) 1.1731(6) 0.2883(3) 0.0543(10) Uani 1 1 d . . .
H9 H 0.2064 1.2813 0.3240 0.065 Uiso 1 1 calc R . .
N1 N 0.16506(14) 0.8098(4) 0.43575(18) 0.0390(7) Uani 1 1 d . . .
Cs1 Cs 0.027354(12) 0.69113(4) 0.610069(16) 0.05427(12) Uani 1 1 d D . .
S1 S 0.13186(4) 0.48625(14) 0.50316(6) 0.0467(2) Uani 1 1 d . . .
S2 S 0.04247(5) 0.81862(14) 0.41933(7) 0.0484(2) Uani 1 1 d . . .
O1 O 0.0000 0.4440(9) 0.7500 0.0711(17) Uani 0.864(8) 2 d SPD . 1
H11 H -0.0317(19) 0.522(8) 0.737(3) 0.107 Uiso 0.432(4) 1 d PD . 1
H12 H -0.014(3) 0.324(4) 0.7408(16) 0.107 Uiso 0.432(4) 1 d PD . 1
O1B O 0.0000 0.914(4) 0.7500 0.048(8) Uani 0.136(8) 2 d SPD . 2
H11B H 0.031(3) 0.995(12) 0.759(5) 0.072 Uiso 0.068(4) 1 d PD . 2
H12B H -0.033(3) 0.985(14) 0.7337(15) 0.072 Uiso 0.068(4) 1 d PD . 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.350(4) . ?
C1 S1 1.704(3) . ?
C1 S2 1.720(3) . ?
C2 C2 1.510(7) 7_566 ?
C2 N1 1.462(5) . ?
C3 N1 1.457(5) . ?
C3 C4 1.513(5) . ?
C4 C5 1.381(5) . ?
C4 C9 1.380(5) . ?
C5 C6 1.377(6) . ?
C6 C7 1.365(6) . ?
C6 Cs1 3.797(5) 6_575 ?
C7 C8 1.368(7) . ?
C7 Cs1 3.508(4) 6_575 ?
C8 C9 1.384(6) . ?
C8 Cs1 3.596(5) 6_575 ?
Cs1 O1B 3.080(12) . ?
Cs1 O1 3.159(3) . ?
Cs1 S1 3.6053(10) 5_566 ?
Cs1 S2 3.5528(11) . ?
Cs1 S2 3.5263(10) 5_576 ?
Cs1 S2 3.6428(11) 5_566 ?
Cs1 S1 3.7192(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S1 120.0(3) . . ?
N1 C1 S2 119.8(3) . . ?
S1 C1 S2 120.2(2) . . ?
N1 C1 Cs1 142.6(2) . . ?
S1 C1 Cs1 69.49(11) . . ?
S2 C1 Cs1 63.90(10) . . ?
N1 C1 Cs1 151.0(2) . 5_566 ?
S1 C1 Cs1 63.48(11) . 5_566 ?
S2 C1 Cs1 64.74(11) . 5_566 ?
Cs1 C1 Cs1 66.39(5) . 5_566 ?
C2 C2 N1 111.7(4) 7_566 . ?
N1 C3 C4 113.0(3) . . ?
C5 C4 C9 118.2(3) . . ?
C5 C4 C3 122.6(3) . . ?
C9 C4 C3 119.2(3) . . ?
C6 C5 C4 120.8(4) . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 Cs1 94.3(3) . 6_575 ?
C7 C6 Cs1 67.4(3) . 6_575 ?
C8 C7 C6 119.7(4) . . ?
C8 C7 Cs1 82.6(3) . 6_575 ?
C6 C7 Cs1 91.5(3) . 6_575 ?
C9 C8 C7 120.1(4) . . ?
C9 C8 Cs1 94.6(3) . 6_575 ?
C7 C8 Cs1 75.3(3) . 6_575 ?
C8 C9 C4 120.7(4) . . ?
C1 N1 C2 121.8(3) . . ?
C1 N1 C3 124.1(3) . . ?
C2 N1 C3 114.0(3) . . ?
O1B Cs1 O1 59.1(4) . . ?
O1B Cs1 S1 98.56(13) . 5_566 ?
O1 Cs1 S1 80.32(3) . 5_566 ?
O1B Cs1 S2 137.6(4) . . ?
O1 Cs1 S2 161.64(9) . . ?
S1 Cs1 S2 88.18(2) 5_566 . ?
O1B Cs1 C7 88.4(3) . 6_576 ?
O1 Cs1 C7 119.96(8) . 6_576 ?
S1 Cs1 C7 158.87(8) 5_566 6_576 ?
S2 Cs1 C7 73.56(7) . 6_576 ?
O1B Cs1 S2 58.8(4) . 5_576 ?
O1 Cs1 S2 112.35(8) . 5_576 ?
S1 Cs1 S2 84.87(2) 5_566 5_576 ?
S2 Cs1 S2 80.51(3) . 5_576 ?
C7 Cs1 S2 81.75(8) 6_576 5_576 ?
O1B Cs1 C8 87.80(13) . 6_576 ?
O1 Cs1 C8 101.37(8) . 6_576 ?
S1 Cs1 C8 173.30(7) 5_566 6_576 ?
S2 Cs1 C8 88.51(8) . 6_576 ?
C7 Cs1 C8 22.15(11) 6_576 6_576 ?
S2 Cs1 C8 100.33(8) 5_576 6_576 ?
O1B Cs1 S2 110.4(4) . 5_566 ?
O1 Cs1 S2 56.53(8) . 5_566 ?
S1 Cs1 S2 48.33(2) 5_566 5_566 ?
S2 Cs1 S2 105.19(2) . 5_566 ?
C7 Cs1 S2 146.37(8) 6_576 5_566 ?
S2 Cs1 S2 131.74(3) 5_576 5_566 ?
C8 Cs1 S2 127.33(8) 6_576 5_566 ?
O1B Cs1 S1 154.54(8) . . ?
O1 Cs1 S1 121.98(8) . . ?
S1 Cs1 S1 106.730(19) 5_566 . ?
S2 Cs1 S1 48.10(2) . . ?
C7 Cs1 S1 68.97(7) 6_576 . ?
S2 Cs1 S1 125.54(2) 5_576 . ?
C8 Cs1 S1 66.82(7) 6_576 . ?
S2 Cs1 S1 85.14(2) 5_566 . ?
O1B Cs1 C6 70.6(3) . 6_576 ?
O1 Cs1 C6 115.70(9) . 6_576 ?
S1 Cs1 C6 147.59(7) 5_566 6_576 ?
S2 Cs1 C6 81.44(7) . 6_576 ?
C7 Cs1 C6 21.06(10) 6_576 6_576 ?
S2 Cs1 C6 63.22(7) 5_576 6_576 ?
C8 Cs1 C6 37.14(10) 6_576 6_576 ?
S2 Cs1 C6 163.95(7) 5_566 6_576 ?
S1 Cs1 C6 88.90(7) . 6_576 ?
O1B Cs1 C1 145.8(4) . . ?
O1 Cs1 C1 147.36(9) . . ?
S1 Cs1 C1 106.38(5) 5_566 . ?
S2 Cs1 C1 25.76(5) . . ?
C7 Cs1 C1 60.46(8) 6_576 . ?
S2 Cs1 C1 100.15(5) 5_576 . ?
C8 Cs1 C1 68.70(9) 6_576 . ?
S2 Cs1 C1 103.60(5) 5_566 . ?
S1 Cs1 C1 25.41(5) . . ?
C6 Cs1 C1 75.87(8) 6_576 . ?
O1B Cs1 C1 98.9(3) . 5_566 ?
O1 Cs1 C1 60.75(7) . 5_566 ?
S1 Cs1 C1 25.01(5) 5_566 5_566 ?
S2 Cs1 C1 103.86(5) . 5_566 ?
C7 Cs1 C1 171.05(9) 6_576 5_566 ?
S2 Cs1 C1 106.47(5) 5_576 5_566 ?
C8 Cs1 C1 151.92(9) 6_576 5_566 ?
S2 Cs1 C1 25.27(5) 5_566 5_566 ?
S1 Cs1 C1 102.80(5) . 5_566 ?
C6 Cs1 C1 167.86(8) 6_576 5_566 ?
C1 Cs1 C1 113.61(5) . 5_566 ?
C1 S1 Cs1 91.51(12) . 5_566 ?
C1 S1 Cs1 85.10(11) . . ?
Cs1 S1 Cs1 73.270(19) 5_566 . ?
C1 S2 Cs1 90.34(12) . . ?
C1 S2 Cs1 138.28(12) . 5_576 ?
Cs1 S2 Cs1 99.49(3) . 5_576 ?
C1 S2 Cs1 89.99(12) . 5_566 ?
Cs1 S2 Cs1 74.81(2) . 5_566 ?
Cs1 S2 Cs1 131.74(3) 5_576 5_566 ?
Cs1 O1 Cs1 118.41(18) 2_556 . ?
Cs1 O1B Cs1 123.5(8) . 2_556 ?

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
N1 C3 C4 C5 33.9(5) . . . . ?
N1 C3 C4 C9 -146.1(4) . . . . ?
C9 C4 C5 C6 0.4(6) . . . . ?
C3 C4 C5 C6 -179.6(4) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
C4 C5 C6 Cs1 -67.1(4) . . . 6_575 ?
C5 C6 C7 C8 1.0(7) . . . . ?
Cs1 C6 C7 C8 82.3(4) 6_575 . . . ?
C5 C6 C7 Cs1 -81.3(4) . . . 6_575 ?
C6 C7 C8 C9 -0.8(7) . . . . ?
Cs1 C7 C8 C9 86.7(4) 6_575 . . . ?
C6 C7 C8 Cs1 -87.5(4) . . . 6_575 ?
C7 C8 C9 C4 0.5(7) . . . . ?
Cs1 C8 C9 C4 76.1(4) 6_575 . . . ?
C5 C4 C9 C8 -0.3(6) . . . . ?
C3 C4 C9 C8 179.8(4) . . . . ?
S1 C1 N1 C2 3.7(4) . . . . ?
S2 C1 N1 C2 -176.0(2) . . . . ?
Cs1 C1 N1 C2 98.9(4) . . . . ?
Cs1 C1 N1 C2 -85.0(5) 5_566 . . . ?
S1 C1 N1 C3 -173.6(3) . . . . ?
S2 C1 N1 C3 6.6(5) . . . . ?
Cs1 C1 N1 C3 -78.4(5) . . . . ?
Cs1 C1 N1 C3 97.6(5) 5_566 . . . ?
C2 C2 N1 C1 -90.0(5) 7_566 . . . ?
C2 C2 N1 C3 87.6(4) 7_566 . . . ?
C4 C3 N1 C1 -111.8(4) . . . . ?
C4 C3 N1 C2 70.7(4) . . . . ?
N1 C1 Cs1 O1B 17.2(6) . . . . ?
S1 C1 Cs1 O1B 130.2(4) . . . . ?
S2 C1 Cs1 O1B -88.5(4) . . . . ?
Cs1 C1 Cs1 O1B -160.7(4) 5_566 . . . ?
N1 C1 Cs1 O1 -109.9(4) . . . . ?
S1 C1 Cs1 O1 3.1(2) . . . . ?
S2 C1 Cs1 O1 144.44(12) . . . . ?
Cs1 C1 Cs1 O1 72.16(13) 5_566 . . . ?
N1 C1 Cs1 S1 152.4(4) . . . 5_566 ?
S1 C1 Cs1 S1 -94.62(11) . . . 5_566 ?
S2 C1 Cs1 S1 46.75(12) . . . 5_566 ?
Cs1 C1 Cs1 S1 -25.53(5) 5_566 . . 5_566 ?
N1 C1 Cs1 S2 105.6(4) . . . . ?
S1 C1 Cs1 S2 -141.4(2) . . . . ?
Cs1 C1 Cs1 S2 -72.28(10) 5_566 . . . ?
N1 C1 Cs1 C7 -9.6(4) . . . 6_576 ?
S1 C1 Cs1 C7 103.40(15) . . . 6_576 ?
S2 C1 Cs1 C7 -115.22(15) . . . 6_576 ?
Cs1 C1 Cs1 C7 172.50(11) 5_566 . . 6_576 ?
N1 C1 Cs1 S2 64.8(4) . . . 5_576 ?
S1 C1 Cs1 S2 177.79(10) . . . 5_576 ?
S2 C1 Cs1 S2 -40.83(12) . . . 5_576 ?
Cs1 C1 Cs1 S2 -113.11(4) 5_566 . . 5_576 ?
N1 C1 Cs1 C8 -32.4(4) . . . 6_576 ?
S1 C1 Cs1 C8 80.57(14) . . . 6_576 ?
S2 C1 Cs1 C8 -138.05(15) . . . 6_576 ?
Cs1 C1 Cs1 C8 149.67(10) 5_566 . . 6_576 ?
N1 C1 Cs1 S2 -157.6(4) . . . 5_566 ?
S1 C1 Cs1 S2 -44.55(12) . . . 5_566 ?
S2 C1 Cs1 S2 96.83(11) . . . 5_566 ?
Cs1 C1 Cs1 S2 24.55(5) 5_566 . . 5_566 ?
N1 C1 Cs1 S1 -113.0(4) . . . . ?
S2 C1 Cs1 S1 141.4(2) . . . . ?
Cs1 C1 Cs1 S1 69.10(10) 5_566 . . . ?
N1 C1 Cs1 C6 5.9(4) . . . 6_576 ?
S1 C1 Cs1 C6 118.93(13) . . . 6_576 ?
S2 C1 Cs1 C6 -99.70(13) . . . 6_576 ?
Cs1 C1 Cs1 C6 -171.98(8) 5_566 . . 6_576 ?
N1 C1 Cs1 C1 177.9(4) . . . 5_566 ?
S1 C1 Cs1 C1 -69.10(10) . . . 5_566 ?
S2 C1 Cs1 C1 72.28(10) . . . 5_566 ?
Cs1 C1 Cs1 C1 0.0 5_566 . . 5_566 ?
N1 C1 S1 Cs1 -147.2(3) . . . 5_566 ?
S2 C1 S1 Cs1 32.6(2) . . . 5_566 ?
Cs1 C1 S1 Cs1 73.07(2) . . . 5_566 ?
N1 C1 S1 Cs1 139.8(3) . . . . ?
S2 C1 S1 Cs1 -40.43(19) . . . . ?
Cs1 C1 S1 Cs1 -73.07(2) 5_566 . . . ?
O1B Cs1 S1 C1 -93.7(10) . . . . ?
O1 Cs1 S1 C1 -178.05(13) . . . . ?
S1 Cs1 S1 C1 93.06(12) 5_566 . . . ?
S2 Cs1 S1 C1 21.38(12) . . . . ?
C7 Cs1 S1 C1 -65.05(14) 6_576 . . . ?
S2 Cs1 S1 C1 -2.67(12) 5_576 . . . ?
C8 Cs1 S1 C1 -88.88(15) 6_576 . . . ?
S2 Cs1 S1 C1 136.82(12) 5_566 . . . ?
C6 Cs1 S1 C1 -58.09(13) 6_576 . . . ?
C1 Cs1 S1 C1 118.62(10) 5_566 . . . ?
O1B Cs1 S1 Cs1 173.2(9) . . . 5_566 ?
O1 Cs1 S1 Cs1 88.89(6) . . . 5_566 ?
S1 Cs1 S1 Cs1 0.0 5_566 . . 5_566 ?
S2 Cs1 S1 Cs1 -71.68(3) . . . 5_566 ?
C7 Cs1 S1 Cs1 -158.11(8) 6_576 . . 5_566 ?
S2 Cs1 S1 Cs1 -95.73(3) 5_576 . . 5_566 ?
C8 Cs1 S1 Cs1 178.06(9) 6_576 . . 5_566 ?
S2 Cs1 S1 Cs1 43.76(2) 5_566 . . 5_566 ?
C6 Cs1 S1 Cs1 -151.16(7) 6_576 . . 5_566 ?
C1 Cs1 S1 Cs1 -93.06(12) . . . 5_566 ?
C1 Cs1 S1 Cs1 25.56(5) 5_566 . . 5_566 ?
N1 C1 S2 Cs1 -137.6(3) . . . . ?
S1 C1 S2 Cs1 42.57(19) . . . . ?
Cs1 C1 S2 Cs1 74.81(2) 5_566 . . . ?
N1 C1 S2 Cs1 -32.9(4) . . . 5_576 ?
S1 C1 S2 Cs1 147.31(13) . . . 5_576 ?
Cs1 C1 S2 Cs1 104.75(14) . . . 5_576 ?
Cs1 C1 S2 Cs1 179.56(15) 5_566 . . 5_576 ?
N1 C1 S2 Cs1 147.6(3) . . . 5_566 ?
S1 C1 S2 Cs1 -32.24(19) . . . 5_566 ?
Cs1 C1 S2 Cs1 -74.81(2) . . . 5_566 ?
O1B Cs1 S2 C1 123.63(16) . . . . ?
O1 Cs1 S2 C1 -84.69(17) . . . . ?
S1 Cs1 S2 C1 -135.64(12) 5_566 . . . ?
C7 Cs1 S2 C1 55.14(14) 6_576 . . . ?
S2 Cs1 S2 C1 139.27(12) 5_576 . . . ?
C8 Cs1 S2 C1 38.54(14) 6_576 . . . ?
S2 Cs1 S2 C1 -89.89(11) 5_566 . . . ?
S1 Cs1 S2 C1 -21.09(11) . . . . ?
C6 Cs1 S2 C1 75.16(13) 6_576 . . . ?
C1 Cs1 S2 C1 -115.98(11) 5_566 . . . ?
O1B Cs1 S2 Cs1 -15.64(11) . . . 5_576 ?
O1 Cs1 S2 Cs1 136.05(12) . . . 5_576 ?
S1 Cs1 S2 Cs1 85.10(3) 5_566 . . 5_576 ?
C7 Cs1 S2 Cs1 -84.13(8) 6_576 . . 5_576 ?
S2 Cs1 S2 Cs1 0.0 5_576 . . 5_576 ?
C8 Cs1 S2 Cs1 -100.73(8) 6_576 . . 5_576 ?
S2 Cs1 S2 Cs1 130.84(3) 5_566 . . 5_576 ?
S1 Cs1 S2 Cs1 -160.35(4) . . . 5_576 ?
C6 Cs1 S2 Cs1 -64.10(7) 6_576 . . 5_576 ?
C1 Cs1 S2 Cs1 -139.27(12) . . . 5_576 ?
C1 Cs1 S2 Cs1 104.76(5) 5_566 . . 5_576 ?
O1B Cs1 S2 Cs1 -146.48(11) . . . 5_566 ?
O1 Cs1 S2 Cs1 5.21(12) . . . 5_566 ?
S1 Cs1 S2 Cs1 -45.745(19) 5_566 . . 5_566 ?
C7 Cs1 S2 Cs1 145.03(8) 6_576 . . 5_566 ?
S2 Cs1 S2 Cs1 -130.84(3) 5_576 . . 5_566 ?
C8 Cs1 S2 Cs1 128.43(7) 6_576 . . 5_566 ?
S2 Cs1 S2 Cs1 0.0 5_566 . . 5_566 ?
S1 Cs1 S2 Cs1 68.80(3) . . . 5_566 ?
C6 Cs1 S2 Cs1 165.06(7) 6_576 . . 5_566 ?
C1 Cs1 S2 Cs1 89.89(11) . . . 5_566 ?
C1 Cs1 S2 Cs1 -26.08(5) 5_566 . . 5_566 ?
O1B Cs1 O1 Cs1 0.0 . . . 2_556 ?
S1 Cs1 O1 Cs1 -106.17(2) 5_566 . . 2_556 ?
S2 Cs1 O1 Cs1 -158.11(12) . . . 2_556 ?
C7 Cs1 O1 Cs1 67.46(10) 6_576 . . 2_556 ?
S2 Cs1 O1 Cs1 -25.86(3) 5_576 . . 2_556 ?
C8 Cs1 O1 Cs1 80.43(7) 6_576 . . 2_556 ?
S2 Cs1 O1 Cs1 -152.09(3) 5_566 . . 2_556 ?
S1 Cs1 O1 Cs1 150.08(4) . . . 2_556 ?
C6 Cs1 O1 Cs1 44.10(8) 6_576 . . 2_556 ?
C1 Cs1 O1 Cs1 148.53(12) . . . 2_556 ?
C1 Cs1 O1 Cs1 -122.81(7) 5_566 . . 2_556 ?
O1 Cs1 O1B Cs1 0.0 . . . 2_556 ?
S1 Cs1 O1B Cs1 73.22(6) 5_566 . . 2_556 ?
S2 Cs1 O1B Cs1 169.97(9) . . . 2_556 ?
C7 Cs1 O1B Cs1 -126.82(8) 6_576 . . 2_556 ?
S2 Cs1 O1B Cs1 151.86(13) 5_576 . . 2_556 ?
C8 Cs1 O1B Cs1 -104.66(8) 6_576 . . 2_556 ?
S2 Cs1 O1B Cs1 24.62(7) 5_566 . . 2_556 ?
S1 Cs1 O1B Cs1 -100.2(9) . . . 2_556 ?
C6 Cs1 O1B Cs1 -138.34(12) 6_576 . . 2_556 ?
C1 Cs1 O1B Cs1 -149.9(3) . . . 2_556 ?
C1 Cs1 O1B Cs1 47.92(7) 5_566 . . 2_556 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.088

# Attachment 'revised_file_Compound_5.cif'

data_sad
_database_code_depnum_ccdc_archive 'CCDC 721772'
_audit_update_record             
;
2009-02-25 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          471.6
_chemical_formula_moiety         'C18 H18 N2 S4, 2(C6 H16 N)'
_chemical_formula_sum            'C30 H50 N4 S4'
_chemical_formula_weight         594.98

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/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                   15.677(3)
_cell_length_b                   10.452(2)
_cell_length_c                   20.855(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.12(3)
_cell_angle_gamma                90.00
_cell_volume                     3328.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1447
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      25.6

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9099
_exptl_absorpt_correction_T_max  0.9349
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8095
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2932
_reflns_number_gt                2168
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT-Plus NT (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus NT'
_computing_structure_solution    'SHELXTL-NT (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL-NT
_computing_molecular_graphics    SHELXTL-NT
_computing_publication_material  ?

_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)+(0.1051P)²+5.3494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.1008
_refine_ls_wR_factor_ref         0.2585
_refine_ls_wR_factor_gt          0.2410
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0854(3) 0.6143(5) 0.1176(2) 0.0464(12) Uani 1 1 d . . .
C2 C 0.0411(3) 0.5404(5) 0.0032(2) 0.0456(12) Uani 1 1 d . . .
H2A H 0.0923 0.4855 0.0140 0.055 Uiso 1 1 calc R . .
H2B H 0.0405 0.5813 -0.0387 0.055 Uiso 1 1 calc R . .
C3 C 0.0070(3) 0.7602(5) 0.0294(3) 0.0506(13) Uani 1 1 d . . .
H3A H 0.0028 0.8134 0.0666 0.061 Uiso 1 1 calc R . .
H3B H -0.0519 0.7449 0.0037 0.061 Uiso 1 1 calc R . .
C4 C 0.0578(3) 0.8305(5) -0.0123(2) 0.0460(12) Uani 1 1 d . . .
C5 C 0.0161(4) 0.8861(6) -0.0708(3) 0.0678(17) Uani 1 1 d . . .
H5 H -0.0445 0.8799 -0.0843 0.081 Uiso 1 1 calc R . .
C6 C 0.0613(6) 0.9504(7) -0.1099(4) 0.082(2) Uani 1 1 d . . .
H6 H 0.0311 0.9872 -0.1491 0.098 Uiso 1 1 calc R . .
C7 C 0.1488(6) 0.9607(6) -0.0920(4) 0.080(2) Uani 1 1 d . . .
H7 H 0.1796 1.0030 -0.1188 0.097 Uiso 1 1 calc R . .
C8 C 0.1920(5) 0.9081(7) -0.0336(4) 0.089(2) Uani 1 1 d . . .
H8 H 0.2526 0.9156 -0.0206 0.106 Uiso 1 1 calc R . .
C9 C 0.1469(4) 0.8437(7) 0.0066(3) 0.0723(18) Uani 1 1 d . . .
H9 H 0.1772 0.8094 0.0464 0.087 Uiso 1 1 calc R . .
C10 C 0.1135(6) 0.4993(8) 0.3319(6) 0.133(4) Uani 1 1 d D . .
H10A H 0.1251 0.5103 0.3793 0.159 Uiso 1 1 calc R . .
H10B H 0.0560 0.5351 0.3138 0.159 Uiso 1 1 calc R . .
C11 C 0.1091(10) 0.3586(8) 0.3179(8) 0.206(7) Uani 1 1 d D . .
H11A H 0.0930 0.3450 0.2712 0.309 Uiso 1 1 calc R . .
H11B H 0.0661 0.3201 0.3381 0.309 Uiso 1 1 calc R . .
H11C H 0.1653 0.3207 0.3356 0.309 Uiso 1 1 calc R . .
C12 C 0.1808(5) 0.7022(6) 0.3413(3) 0.0706(18) Uani 1 1 d . . .
H12A H 0.1208 0.7313 0.3358 0.085 Uiso 1 1 calc R . .
H12B H 0.2117 0.7650 0.3209 0.085 Uiso 1 1 calc R . .
C13 C 0.2225(6) 0.6969(8) 0.4137(3) 0.096(3) Uani 1 1 d . . .
H13A H 0.1893 0.6410 0.4352 0.144 Uiso 1 1 calc R . .
H13B H 0.2236 0.7812 0.4322 0.144 Uiso 1 1 calc R . .
H13C H 0.2813 0.6652 0.4199 0.144 Uiso 1 1 calc R . .
C14 C 0.2642(5) 0.5208(8) 0.3079(4) 0.094(2) Uani 1 1 d . . .
H14A H 0.2551 0.4395 0.2850 0.113 Uiso 1 1 calc R . .
H14B H 0.2941 0.5043 0.3532 0.113 Uiso 1 1 calc R . .
C15 C 0.3214(5) 0.6054(9) 0.2759(4) 0.113(3) Uani 1 1 d . . .
H15A H 0.2888 0.6323 0.2334 0.169 Uiso 1 1 calc R . .
H15B H 0.3721 0.5583 0.2711 0.169 Uiso 1 1 calc R . .
H15C H 0.3394 0.6791 0.3030 0.169 Uiso 1 1 calc R . .
H2 H 0.154(5) 0.596(7) 0.264(4) 0.10(2) Uiso 1 1 d . . .
N1 N 0.0471(3) 0.6375(4) 0.05373(18) 0.0427(10) Uani 1 1 d . . .
N2 N 0.1805(3) 0.5794(5) 0.3065(2) 0.0610(13) Uani 1 1 d . . .
S1 S 0.12759(10) 0.46633(14) 0.14027(7) 0.0603(5) Uani 1 1 d . . .
S2 S 0.08806(11) 0.73296(15) 0.17467(7) 0.0648(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.354(6) . ?
C1 S1 1.706(5) . ?
C1 S2 1.713(5) . ?
C2 N1 1.452(6) . ?
C2 C2 1.522(9) 5_565 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.466(6) . ?
C3 C4 1.498(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.369(8) . ?
C4 C5 1.376(7) . ?
C5 C6 1.371(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.341(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(9) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.4979(11) . ?
C10 N2 1.529(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N2 1.473(7) . ?
C12 C13 1.504(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.443(8) . ?
C14 C15 1.516(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N2 H2 0.91(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S1 119.5(4) . . ?
N1 C1 S2 119.3(4) . . ?
S1 C1 S2 121.2(3) . . ?
N1 C2 C2 111.3(5) . 5_565 ?
N1 C2 H2A 109.4 . . ?
C2 C2 H2A 109.4 5_565 . ?
N1 C2 H2B 109.4 . . ?
C2 C2 H2B 109.4 5_565 . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C4 112.8(4) . . ?
N1 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C9 C4 C5 117.4(5) . . ?
C9 C4 C3 121.6(5) . . ?
C5 C4 C3 121.0(5) . . ?
C6 C5 C4 122.0(6) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C7 C6 C5 120.5(7) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 119.0(7) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C9 121.1(7) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C8 120.1(6) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 N2 118.4(8) . . ?
C11 C10 H10A 107.7 . . ?
N2 C10 H10A 107.7 . . ?
C11 C10 H10B 107.7 . . ?
N2 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 114.5(6) . . ?
N2 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N2 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.7(7) . . ?
N2 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C2 122.0(4) . . ?
C1 N1 C3 123.9(4) . . ?
C2 N1 C3 114.1(4) . . ?
C14 N2 C12 117.3(5) . . ?
C14 N2 C10 117.0(6) . . ?
C12 N2 C10 103.4(6) . . ?
C14 N2 H2 108(4) . . ?
C12 N2 H2 105(5) . . ?
C10 N2 H2 104(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
N1 C3 C4 C9 -46.2(7) . . . . ?
N1 C3 C4 C5 134.8(5) . . . . ?
C9 C4 C5 C6 1.3(9) . . . . ?
C3 C4 C5 C6 -179.7(6) . . . . ?
C4 C5 C6 C7 0.2(11) . . . . ?
C5 C6 C7 C8 -1.2(11) . . . . ?
C6 C7 C8 C9 0.7(11) . . . . ?
C5 C4 C9 C8 -1.7(9) . . . . ?
C3 C4 C9 C8 179.2(6) . . . . ?
C7 C8 C9 C4 0.8(11) . . . . ?
S1 C1 N1 C2 -0.6(6) . . . . ?
S2 C1 N1 C2 -178.8(3) . . . . ?
S1 C1 N1 C3 178.5(4) . . . . ?
S2 C1 N1 C3 0.3(6) . . . . ?
C2 C2 N1 C1 87.9(7) 5_565 . . . ?
C2 C2 N1 C3 -91.3(6) 5_565 . . . ?
C4 C3 N1 C1 110.4(5) . . . . ?
C4 C3 N1 C2 -70.4(5) . . . . ?
C15 C14 N2 C12 -61.3(8) . . . . ?
C15 C14 N2 C10 174.9(7) . . . . ?
C13 C12 N2 C14 -59.4(9) . . . . ?
C13 C12 N2 C10 71.0(8) . . . . ?
C11 C10 N2 C14 -36.9(13) . . . . ?
C11 C10 N2 C12 -167.5(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.074


