# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222

_publ_contact_author_name        'Prof. Dr. Ulrich Siemeling'
_publ_contact_author_address     
;
Institute for Chemistry
University of Kassel
D-34109 Kassel
Germany
;
_publ_contact_author_phone       '+0049 561 804 4576'
_publ_contact_author_fax         '+0049 561 804 4777'
_publ_contact_author_email       siemeling@uni-kassel.de
_publ_requested_category         ?
_publ_requested_coeditor_name    ?
_publ_contact_letter             
;
The CIF has passed the Chester CHECKCIF routines.
;
#=====================================================================

# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#=====================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Zwitterionic dithiocarboxylates derived from N-heterocyclic carbenes:
coordination to gold surfaces.
;

loop_
_publ_author_name
_publ_author_footnote
_publ_author_address

U.Siemeling ?
;
Institute of Chemistry
University of Kassel
D-34109 Kassel
Germany
;
H.Memczak ?
;
Institute of Chemistry
University of Kassel
D-34109 Kassel
Germany
;
C.Bruhn ?
;
Institute of Chemistry
University of Kassel
D-34109 Kassel
Germany
;
F.Vogel ?
;
Institute of Physics
University of Kassel
D-34109 Kassel
Germany
;
F.Trager ?
;
Institute of Physics
University of Kassel
D-34109 Kassel
Germany
;
J.E.Baio ?
;
National ESCA and Surface Analysis Center for Biomedical Problems (NESAC/BIO)
Departments of Bioengineering and Chemical Engineering
University of Washington
Seattle, Washington 98195
USA
;
T.Weidner ?
;
National ESCA and Surface Analysis Center for Biomedical Problems (NESAC/BIO)
Departments of Bioengineering and Chemical Engineering
University of Washington
Seattle, Washington 98195
USA
;

#======================================================================
data_i0711
_database_code_depnum_ccdc_archive 'CCDC 847616'
#TrackingRef 'publus88.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 N2 S2'
_chemical_formula_weight         228.37
_chemical_absolute_configuration .

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2'
_symmetry_Int_Tables_number      92

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+3/4'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'y+1/2, -x+1/2, z+3/4'
'-y+1/2, x+1/2, z+1/4'
'-y, -x, -z+1/2'

_cell_length_a                   9.2048(4)
_cell_length_b                   9.2048(4)
_cell_length_c                   28.6900(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2430.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7544
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.53

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8520
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 60 frames, detector distance = 135 mm
;

_diffrn_standards_decay_%        none
_diffrn_reflns_number            5036
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1230
_reflns_number_gt                1148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details
# 'Flack H D (1983), Acta Cryst. A39, 876-881'
# _refine_ls_abs_structure_Flack 0(10)
_refine_ls_number_reflns         1230
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
C1 C 0.4508(3) 0.2317(3) 0.70486(10) 0.0267(5) Uani 1 1 d . . .
C2 C 0.4028(2) 0.1872(3) 0.75216(10) 0.0288(6) Uani 1 1 d . . .
C3 C 0.5596(3) 0.2304(3) 0.63517(10) 0.0303(6) Uani 1 1 d . . .
H3A H 0.6235 0.2054 0.6104 0.036 Uiso 1 1 calc R . .
C4 C 0.4531(3) 0.3328(3) 0.63401(10) 0.0300(6) Uani 1 1 d . . .
H4A H 0.4279 0.3920 0.6081 0.036 Uiso 1 1 calc R . .
C5 C 0.6594(3) 0.0577(3) 0.69755(11) 0.0294(6) Uani 1 1 d . . .
H5A H 0.6479 0.0525 0.7322 0.035 Uiso 1 1 calc R . .
C6 C 0.6210(3) -0.0902(3) 0.67720(13) 0.0374(7) Uani 1 1 d . . .
H6A H 0.6843 -0.1646 0.6908 0.045 Uiso 1 1 calc R . .
H6B H 0.6345 -0.0881 0.6433 0.045 Uiso 1 1 calc R . .
H6C H 0.5195 -0.1131 0.6844 0.045 Uiso 1 1 calc R . .
C7 C 0.8152(3) 0.1031(3) 0.68679(13) 0.0393(7) Uani 1 1 d . . .
H7C H 0.8316 0.2023 0.6980 0.047 Uiso 1 1 calc R . .
H7B H 0.8314 0.0994 0.6530 0.047 Uiso 1 1 calc R . .
H7A H 0.8828 0.0367 0.7024 0.047 Uiso 1 1 calc R . .
C8 C 0.2698(3) 0.4335(3) 0.69312(11) 0.0326(6) Uani 1 1 d . . .
H8A H 0.2558 0.4202 0.7274 0.039 Uiso 1 1 calc R . .
C9 C 0.3141(4) 0.5902(3) 0.68439(18) 0.0579(11) Uani 1 1 d . . .
H9A H 0.2433 0.6556 0.6989 0.069 Uiso 1 1 calc R . .
H9B H 0.3174 0.6085 0.6508 0.069 Uiso 1 1 calc R . .
H9C H 0.4104 0.6077 0.6979 0.069 Uiso 1 1 calc R . .
C10 C 0.1291(3) 0.3943(4) 0.66894(17) 0.0592(11) Uani 1 1 d . . .
H10C H 0.1039 0.2933 0.6760 0.071 Uiso 1 1 calc R . .
H10B H 0.1409 0.4057 0.6352 0.071 Uiso 1 1 calc R . .
H10A H 0.0514 0.4586 0.6799 0.071 Uiso 1 1 calc R . .
N1 N 0.5573(2) 0.1697(2) 0.67932(9) 0.0278(5) Uani 1 1 d . . .
N2 N 0.3880(2) 0.3345(2) 0.67764(9) 0.0291(5) Uani 1 1 d . . .
S1 S 0.48277(7) 0.27226(7) 0.79705(3) 0.0324(2) Uani 1 1 d . . .
S2 S 0.27488(8) 0.05783(7) 0.75144(3) 0.0392(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0256(11) 0.0289(12) 0.0255(13) -0.0009(11) 0.0000(10) -0.0008(9)
C2 0.0259(11) 0.0275(12) 0.0330(15) 0.0019(11) 0.0028(11) 0.0050(9)
C3 0.0310(12) 0.0339(13) 0.0260(14) 0.0024(11) 0.0033(10) -0.0023(10)
C4 0.0326(12) 0.0327(13) 0.0249(14) 0.0044(11) 0.0020(11) -0.0004(10)
C5 0.0296(12) 0.0296(12) 0.0289(14) -0.0002(11) -0.0018(11) 0.0052(10)
C6 0.0370(14) 0.0314(13) 0.0438(18) 0.0000(12) -0.0027(13) 0.0041(11)
C7 0.0308(14) 0.0392(14) 0.048(2) -0.0021(14) 0.0001(12) 0.0036(11)
C8 0.0294(12) 0.0328(13) 0.0357(16) 0.0029(11) 0.0012(11) 0.0081(11)
C9 0.0464(18) 0.0350(15) 0.092(3) 0.0046(18) 0.0115(19) 0.0099(14)
C10 0.0277(14) 0.068(2) 0.082(3) -0.019(2) -0.0031(16) 0.0080(14)
N1 0.0278(10) 0.0289(10) 0.0268(12) 0.0019(9) 0.0037(9) 0.0025(8)
N2 0.0288(10) 0.0280(11) 0.0304(13) 0.0032(9) 0.0016(9) 0.0021(8)
S1 0.0327(3) 0.0372(4) 0.0275(4) 0.0007(3) 0.0008(3) -0.0015(3)
S2 0.0403(4) 0.0385(4) 0.0387(4) 0.0012(3) 0.0048(3) -0.0111(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
C1 N1 1.351(3) . ?
C1 N2 1.356(3) . ?
C1 C2 1.485(4) . ?
C2 S2 1.675(3) . ?
C2 S1 1.677(3) . ?
C3 C4 1.361(4) . ?
C3 N1 1.385(4) . ?
C3 H3A 0.9500 . ?
C4 N2 1.388(4) . ?
C4 H4A 0.9500 . ?
C5 N1 1.490(3) . ?
C5 C6 1.523(4) . ?
C5 C7 1.525(4) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7A 0.9800 . ?
C8 N2 1.487(3) . ?
C8 C10 1.512(4) . ?
C8 C9 1.520(4) . ?
C8 H8A 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10A 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
N1 C1 N2 107.0(2) . . ?
N1 C1 C2 126.5(2) . . ?
N2 C1 C2 126.3(2) . . ?
C1 C2 S2 113.20(19) . . ?
C1 C2 S1 116.28(18) . . ?
S2 C2 S1 130.52(17) . . ?
C4 C3 N1 106.9(2) . . ?
C4 C3 H3A 126.5 . . ?
N1 C3 H3A 126.5 . . ?
C3 C4 N2 107.3(2) . . ?
C3 C4 H4A 126.4 . . ?
N2 C4 H4A 126.4 . . ?
N1 C5 C6 109.7(2) . . ?
N1 C5 C7 109.4(2) . . ?
C6 C5 C7 112.7(2) . . ?
N1 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C7 C5 H5A 108.3 . . ?
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 . . ?
C5 C7 H7C 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
C5 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
N2 C8 C10 110.1(2) . . ?
N2 C8 C9 109.6(2) . . ?
C10 C8 C9 112.4(3) . . ?
N2 C8 H8A 108.2 . . ?
C10 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10C 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
C8 C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
C1 N1 C3 109.7(2) . . ?
C1 N1 C5 124.1(2) . . ?
C3 N1 C5 126.2(2) . . ?
C1 N2 C4 109.1(2) . . ?
C1 N2 C8 124.6(2) . . ?
C4 N2 C8 126.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 S2 -87.6(3) . . . . ?
N2 C1 C2 S2 86.6(3) . . . . ?
N1 C1 C2 S1 92.5(3) . . . . ?
N2 C1 C2 S1 -93.3(3) . . . . ?
N1 C3 C4 N2 0.7(3) . . . . ?
N2 C1 N1 C3 -1.7(3) . . . . ?
C2 C1 N1 C3 173.4(2) . . . . ?
N2 C1 N1 C5 175.8(2) . . . . ?
C2 C1 N1 C5 -9.0(4) . . . . ?
C4 C3 N1 C1 0.6(3) . . . . ?
C4 C3 N1 C5 -176.9(2) . . . . ?
C6 C5 N1 C1 107.0(3) . . . . ?
C7 C5 N1 C1 -128.9(3) . . . . ?
C6 C5 N1 C3 -75.8(3) . . . . ?
C7 C5 N1 C3 48.3(4) . . . . ?
N1 C1 N2 C4 2.1(3) . . . . ?
C2 C1 N2 C4 -173.0(2) . . . . ?
N1 C1 N2 C8 -177.1(2) . . . . ?
C2 C1 N2 C8 7.8(4) . . . . ?
C3 C4 N2 C1 -1.8(3) . . . . ?
C3 C4 N2 C8 177.4(2) . . . . ?
C10 C8 N2 C1 -110.3(3) . . . . ?
C9 C8 N2 C1 125.7(3) . . . . ?
C10 C8 N2 C4 70.7(4) . . . . ?
C9 C8 N2 C4 -53.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.926
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.926
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.049
#======================================================================
data_i0726
_database_code_depnum_ccdc_archive 'CCDC 847617'
#TrackingRef 'publus88.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 S2'
_chemical_formula_sum            'C18 H16 N2 S2'
_chemical_formula_weight         324.45

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   'P 21/c'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.5106(15)
_cell_length_b                   18.013(2)
_cell_length_c                   16.037(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.115(10)
_cell_angle_gamma                90.00
_cell_volume                     3324.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    15946
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      25.25

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8644
_exptl_absorpt_correction_T_max  0.9659
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 180 frames, detector distance = 135 mm
;

_diffrn_standards_decay_%        none
_diffrn_reflns_number            21202
_diffrn_reflns_av_R_equivalents  0.1497
_diffrn_reflns_av_sigmaI/netI    0.1013
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.36
_reflns_number_total             5974
_reflns_number_gt                3083
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         5974
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2333
_refine_ls_wR_factor_gt          0.2047
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_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 0.3791(4) 0.2584(2) 1.0499(3) 0.0492(10) Uani 1 1 d . . .
C2 C 0.3807(4) 0.2566(2) 0.9560(3) 0.0493(11) Uani 1 1 d . . .
C3 C 0.4231(5) 0.2847(3) 1.1832(3) 0.0643(13) Uani 1 1 d . . .
H3A H 0.4593 0.3064 1.2311 0.077 Uiso 1 1 calc R . .
C4 C 0.3381(4) 0.2340(3) 1.1829(3) 0.0586(12) Uani 1 1 d . . .
H4A H 0.3034 0.2125 1.2304 0.070 Uiso 1 1 calc R . .
C5 C 0.5320(4) 0.3571(3) 1.0725(3) 0.0674(14) Uani 1 1 d . . .
H5B H 0.5352 0.3572 1.0108 0.081 Uiso 1 1 calc R . .
H5A H 0.6106 0.3449 1.0947 0.081 Uiso 1 1 calc R . .
C6 C 0.4968(4) 0.4336(3) 1.1028(3) 0.0637(13) Uani 1 1 d . . .
C7 C 0.3870(5) 0.4627(3) 1.0847(4) 0.0751(15) Uani 1 1 d . . .
H7A H 0.3320 0.4335 1.0544 0.090 Uiso 1 1 calc R . .
C8 C 0.3568(6) 0.5326(4) 1.1096(4) 0.0874(18) Uani 1 1 d . . .
H8A H 0.2811 0.5514 1.0979 0.105 Uiso 1 1 calc R . .
C9 C 0.4391(8) 0.5763(4) 1.1528(4) 0.098(2) Uani 1 1 d . . .
H9A H 0.4204 0.6256 1.1685 0.118 Uiso 1 1 calc R . .
C10 C 0.5465(7) 0.5477(4) 1.1724(4) 0.094(2) Uani 1 1 d . . .
H10A H 0.6012 0.5769 1.2030 0.113 Uiso 1 1 calc R . .
C11 C 0.5759(5) 0.4770(4) 1.1479(4) 0.0788(16) Uani 1 1 d . . .
H11A H 0.6505 0.4577 1.1620 0.095 Uiso 1 1 calc R . .
C12 C 0.2237(4) 0.1627(3) 1.0717(3) 0.0579(12) Uani 1 1 d . . .
H12B H 0.2153 0.1641 1.0102 0.069 Uiso 1 1 calc R . .
H12A H 0.1474 0.1753 1.0954 0.069 Uiso 1 1 calc R . .
C13 C 0.2573(4) 0.0855(3) 1.0984(3) 0.0547(11) Uani 1 1 d . . .
C14 C 0.1889(4) 0.0444(3) 1.1517(3) 0.0616(13) Uani 1 1 d . . .
H14A H 0.1195 0.0658 1.1720 0.074 Uiso 1 1 calc R . .
C15 C 0.2189(4) -0.0264(3) 1.1761(3) 0.0662(13) Uani 1 1 d . . .
H15A H 0.1707 -0.0534 1.2128 0.079 Uiso 1 1 calc R . .
C16 C 0.3206(4) -0.0583(3) 1.1464(3) 0.0618(12) Uani 1 1 d . . .
H16A H 0.3421 -0.1073 1.1626 0.074 Uiso 1 1 calc R . .
C17 C 0.3896(4) -0.0179(3) 1.0933(3) 0.0631(13) Uani 1 1 d . . .
H17A H 0.4592 -0.0392 1.0731 0.076 Uiso 1 1 calc R . .
C18 C 0.3580(4) 0.0533(3) 1.0695(3) 0.0598(12) Uani 1 1 d . . .
H18A H 0.4060 0.0804 1.0328 0.072 Uiso 1 1 calc R . .
C19 C -0.1190(4) 0.2392(2) 1.1069(3) 0.0503(10) Uani 1 1 d . . .
C20 C -0.1165(4) 0.2451(3) 1.2003(3) 0.0541(11) Uani 1 1 d . . .
C21 C -0.1703(5) 0.2073(3) 0.9762(3) 0.0769(16) Uani 1 1 d . . .
H21A H -0.2097 0.1846 0.9303 0.092 Uiso 1 1 calc R . .
C22 C -0.0819(6) 0.2543(3) 0.9722(3) 0.0741(15) Uani 1 1 d . . .
H22A H -0.0467 0.2713 0.9226 0.089 Uiso 1 1 calc R . .
C23 C -0.2814(5) 0.1448(3) 1.0911(4) 0.0755(16) Uani 1 1 d . . .
H23B H -0.3456 0.1413 1.0493 0.091 Uiso 1 1 calc R . .
H23A H -0.3141 0.1653 1.1429 0.091 Uiso 1 1 calc R . .
C24 C -0.2374(5) 0.0679(3) 1.1091(3) 0.0656(14) Uani 1 1 d . . .
C25 C -0.3098(5) 0.0183(4) 1.1488(3) 0.0830(18) Uani 1 1 d . . .
H25A H -0.3841 0.0342 1.1663 0.100 Uiso 1 1 calc R . .
C26 C -0.2751(7) -0.0545(5) 1.1633(4) 0.100(2) Uani 1 1 d . . .
H26A H -0.3257 -0.0876 1.1910 0.120 Uiso 1 1 calc R . .
C27 C -0.1679(8) -0.0795(4) 1.1379(4) 0.093(2) Uani 1 1 d . . .
H27A H -0.1447 -0.1295 1.1474 0.111 Uiso 1 1 calc R . .
C28 C -0.0963(6) -0.0308(4) 1.0989(4) 0.0838(17) Uani 1 1 d . . .
H28A H -0.0221 -0.0472 1.0817 0.101 Uiso 1 1 calc R . .
C29 C -0.1292(5) 0.0423(3) 1.0837(3) 0.0698(14) Uani 1 1 d . . .
H29A H -0.0779 0.0749 1.0560 0.084 Uiso 1 1 calc R . .
C30 C 0.0426(4) 0.3282(3) 1.0753(3) 0.0629(13) Uani 1 1 d . . .
H30B H 0.0951 0.3330 1.0275 0.075 Uiso 1 1 calc R . .
H30A H 0.0888 0.3081 1.1229 0.075 Uiso 1 1 calc R . .
C31 C -0.0004(4) 0.4046(3) 1.0984(3) 0.0554(11) Uani 1 1 d . . .
C32 C -0.1006(4) 0.4357(3) 1.0639(3) 0.0614(13) Uani 1 1 d . . .
H32A H -0.1483 0.4071 1.0272 0.074 Uiso 1 1 calc R . .
C33 C -0.1315(4) 0.5071(3) 1.0822(3) 0.0659(14) Uani 1 1 d . . .
H33A H -0.2000 0.5276 1.0574 0.079 Uiso 1 1 calc R . .
C34 C -0.0651(5) 0.5500(3) 1.1360(3) 0.0668(13) Uani 1 1 d . . .
H34A H -0.0873 0.5995 1.1485 0.080 Uiso 1 1 calc R . .
C35 C 0.0351(5) 0.5192(3) 1.1717(3) 0.0744(15) Uani 1 1 d . . .
H35A H 0.0821 0.5477 1.2091 0.089 Uiso 1 1 calc R . .
C36 C 0.0659(5) 0.4472(3) 1.1527(3) 0.0671(14) Uani 1 1 d . . .
H36A H 0.1342 0.4265 1.1776 0.080 Uiso 1 1 calc R . .
N1 N 0.4490(3) 0.2999(2) 1.0995(2) 0.0561(10) Uani 1 1 d . . .
N2 N 0.3098(3) 0.2186(2) 1.0987(2) 0.0519(9) Uani 1 1 d . . .
N3 N -0.1946(4) 0.1974(2) 1.0601(3) 0.0634(11) Uani 1 1 d . . .
N4 N -0.0493(4) 0.2747(2) 1.0533(2) 0.0586(10) Uani 1 1 d . . .
S1 S 0.49621(11) 0.21406(8) 0.91591(8) 0.0649(4) Uani 1 1 d . . .
S2 S 0.26629(11) 0.29624(8) 0.90765(8) 0.0646(4) Uani 1 1 d . . .
S3 S -0.23805(12) 0.27782(9) 1.24302(9) 0.0729(4) Uani 1 1 d . . .
S4 S 0.00861(12) 0.21983(9) 1.24709(8) 0.0701(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.046(2) 0.050(3) 0.051(2) 0.001(2) -0.003(2) 0.002(2)
C2 0.058(3) 0.047(2) 0.043(2) 0.0022(19) 0.002(2) -0.002(2)
C3 0.068(3) 0.071(3) 0.053(3) -0.004(2) -0.012(2) 0.001(3)
C4 0.065(3) 0.067(3) 0.044(2) -0.002(2) -0.002(2) 0.006(3)
C5 0.057(3) 0.086(4) 0.059(3) 0.000(3) -0.005(2) -0.010(3)
C6 0.063(3) 0.074(3) 0.053(3) 0.007(2) -0.003(2) -0.012(3)
C7 0.076(4) 0.077(4) 0.072(4) 0.002(3) -0.018(3) -0.004(3)
C8 0.102(5) 0.080(4) 0.079(4) 0.017(3) -0.003(4) 0.005(4)
C9 0.153(7) 0.067(4) 0.076(4) 0.007(3) 0.022(4) -0.020(5)
C10 0.111(6) 0.096(5) 0.075(4) -0.009(4) 0.004(4) -0.032(4)
C11 0.072(4) 0.096(4) 0.069(4) -0.006(3) -0.005(3) -0.028(3)
C12 0.053(3) 0.063(3) 0.058(3) 0.003(2) -0.004(2) 0.002(2)
C13 0.051(3) 0.058(3) 0.055(3) 0.000(2) -0.002(2) 0.000(2)
C14 0.051(3) 0.069(3) 0.066(3) 0.008(2) 0.010(2) 0.003(2)
C15 0.057(3) 0.071(3) 0.071(3) 0.010(3) 0.005(2) 0.000(3)
C16 0.059(3) 0.058(3) 0.069(3) 0.004(2) -0.003(2) 0.002(2)
C17 0.058(3) 0.062(3) 0.069(3) -0.004(3) 0.004(2) 0.004(2)
C18 0.059(3) 0.061(3) 0.060(3) -0.001(2) 0.011(2) -0.001(2)
C19 0.051(2) 0.051(3) 0.049(2) 0.000(2) -0.001(2) 0.002(2)
C20 0.062(3) 0.052(3) 0.048(2) -0.004(2) 0.000(2) 0.002(2)
C21 0.086(4) 0.090(4) 0.055(3) -0.012(3) -0.011(3) 0.002(3)
C22 0.095(4) 0.079(4) 0.049(3) -0.001(3) 0.005(3) 0.010(3)
C23 0.059(3) 0.084(4) 0.084(4) -0.018(3) -0.004(3) -0.013(3)
C24 0.064(3) 0.082(4) 0.051(3) -0.011(3) -0.010(2) -0.015(3)
C25 0.077(4) 0.115(5) 0.057(3) 0.004(3) -0.006(3) -0.028(4)
C26 0.108(6) 0.119(6) 0.073(4) 0.022(4) -0.016(4) -0.045(5)
C27 0.127(6) 0.077(4) 0.074(4) 0.005(3) -0.023(4) -0.020(4)
C28 0.095(5) 0.080(4) 0.075(4) -0.012(3) -0.007(3) -0.001(4)
C29 0.068(3) 0.075(4) 0.066(3) -0.006(3) 0.002(3) -0.009(3)
C30 0.054(3) 0.065(3) 0.070(3) 0.011(3) 0.005(2) 0.003(2)
C31 0.050(3) 0.056(3) 0.061(3) 0.007(2) 0.005(2) 0.003(2)
C32 0.050(3) 0.062(3) 0.072(3) 0.003(2) -0.007(2) 0.001(2)
C33 0.053(3) 0.066(3) 0.079(4) 0.013(3) -0.005(3) 0.007(2)
C34 0.072(3) 0.064(3) 0.064(3) -0.005(3) 0.000(3) 0.006(3)
C35 0.071(3) 0.085(4) 0.067(3) -0.016(3) -0.015(3) 0.008(3)
C36 0.059(3) 0.078(4) 0.064(3) -0.004(3) -0.011(2) 0.011(3)
N1 0.059(2) 0.062(2) 0.047(2) 0.0026(18) 0.0012(17) -0.004(2)
N2 0.054(2) 0.057(2) 0.045(2) -0.0013(17) 0.0017(17) 0.0032(19)
N3 0.066(3) 0.071(3) 0.053(2) -0.009(2) -0.009(2) -0.003(2)
N4 0.068(3) 0.058(2) 0.050(2) -0.0027(18) 0.0005(19) 0.005(2)
S1 0.0591(8) 0.0802(9) 0.0555(7) -0.0018(6) 0.0008(6) 0.0157(7)
S2 0.0556(7) 0.0851(10) 0.0530(7) 0.0067(6) -0.0024(5) 0.0154(7)
S3 0.0599(8) 0.0971(11) 0.0617(8) -0.0131(7) 0.0015(6) 0.0158(7)
S4 0.0605(8) 0.0964(11) 0.0530(7) 0.0030(7) -0.0061(6) 0.0165(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
C1 N2 1.337(6) . ?
C1 N1 1.346(6) . ?
C1 C2 1.507(6) . ?
C2 S1 1.674(5) . ?
C2 S2 1.675(5) . ?
C3 C4 1.338(7) . ?
C3 N1 1.408(6) . ?
C3 H3A 0.9500 . ?
C4 N2 1.410(6) . ?
C4 H4A 0.9500 . ?
C5 N1 1.476(6) . ?
C5 C6 1.519(8) . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C11 1.393(7) . ?
C6 C7 1.394(7) . ?
C7 C8 1.368(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.403(10) . ?
C8 H8A 0.9500 . ?
C9 C10 1.370(10) . ?
C9 H9A 0.9500 . ?
C10 C11 1.376(9) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 N2 1.472(6) . ?
C12 C13 1.504(7) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C18 1.384(7) . ?
C13 C14 1.387(7) . ?
C14 C15 1.376(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.397(7) . ?
C15 H15A 0.9500 . ?
C16 C17 1.383(7) . ?
C16 H16A 0.9500 . ?
C17 C18 1.386(7) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 N4 1.348(6) . ?
C19 N3 1.365(6) . ?
C19 C20 1.500(6) . ?
C20 S4 1.674(5) . ?
C20 S3 1.677(5) . ?
C21 C22 1.326(8) . ?
C21 N3 1.391(7) . ?
C21 H21A 0.9500 . ?
C22 N4 1.396(6) . ?
C22 H22A 0.9500 . ?
C23 N3 1.469(7) . ?
C23 C24 1.501(8) . ?
C23 H23B 0.9900 . ?
C23 H23A 0.9900 . ?
C24 C25 1.386(8) . ?
C24 C29 1.396(8) . ?
C25 C26 1.389(10) . ?
C25 H25A 0.9500 . ?
C26 C27 1.382(10) . ?
C26 H26A 0.9500 . ?
C27 C28 1.364(9) . ?
C27 H27A 0.9500 . ?
C28 C29 1.391(8) . ?
C28 H28A 0.9500 . ?
C29 H29A 0.9500 . ?
C30 N4 1.469(6) . ?
C30 C31 1.511(7) . ?
C30 H30B 0.9900 . ?
C30 H30A 0.9900 . ?
C31 C36 1.380(7) . ?
C31 C32 1.388(6) . ?
C32 C33 1.368(7) . ?
C32 H32A 0.9500 . ?
C33 C34 1.377(7) . ?
C33 H33A 0.9500 . ?
C34 C35 1.394(7) . ?
C34 H34A 0.9500 . ?
C35 C36 1.380(7) . ?
C35 H35A 0.9500 . ?
C36 H36A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 108.0(4) . . ?
N2 C1 C2 126.3(4) . . ?
N1 C1 C2 125.7(4) . . ?
C1 C2 S1 114.8(3) . . ?
C1 C2 S2 115.4(3) . . ?
S1 C2 S2 129.8(3) . . ?
C4 C3 N1 107.3(4) . . ?
C4 C3 H3A 126.4 . . ?
N1 C3 H3A 126.4 . . ?
C3 C4 N2 107.1(4) . . ?
C3 C4 H4A 126.4 . . ?
N2 C4 H4A 126.4 . . ?
N1 C5 C6 111.2(4) . . ?
N1 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
H5B C5 H5A 108.0 . . ?
C11 C6 C7 118.5(6) . . ?
C11 C6 C5 120.1(5) . . ?
C7 C6 C5 121.4(5) . . ?
C8 C7 C6 121.4(6) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C9 119.1(7) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C8 120.0(7) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 120.5(6) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C6 120.4(6) . . ?
C10 C11 H11A 119.8 . . ?
C6 C11 H11A 119.8 . . ?
N2 C12 C13 112.4(4) . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
H12B C12 H12A 107.9 . . ?
C18 C13 C14 118.2(5) . . ?
C18 C13 C12 120.2(4) . . ?
C14 C13 C12 121.6(4) . . ?
C15 C14 C13 121.8(5) . . ?
C15 C14 H14A 119.1 . . ?
C13 C14 H14A 119.1 . . ?
C14 C15 C16 119.5(5) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16A 120.4 . . ?
C15 C16 H16A 120.4 . . ?
C16 C17 C18 120.4(5) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C13 C18 C17 120.8(5) . . ?
C13 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
N4 C19 N3 107.0(4) . . ?
N4 C19 C20 127.0(4) . . ?
N3 C19 C20 126.0(4) . . ?
C19 C20 S4 115.4(3) . . ?
C19 C20 S3 115.6(3) . . ?
S4 C20 S3 129.0(3) . . ?
C22 C21 N3 107.4(5) . . ?
C22 C21 H21A 126.3 . . ?
N3 C21 H21A 126.3 . . ?
C21 C22 N4 108.3(5) . . ?
C21 C22 H22A 125.8 . . ?
N4 C22 H22A 125.8 . . ?
N3 C23 C24 115.5(5) . . ?
N3 C23 H23B 108.4 . . ?
C24 C23 H23B 108.4 . . ?
N3 C23 H23A 108.4 . . ?
C24 C23 H23A 108.4 . . ?
H23B C23 H23A 107.5 . . ?
C25 C24 C29 117.9(6) . . ?
C25 C24 C23 118.7(5) . . ?
C29 C24 C23 123.3(5) . . ?
C26 C25 C24 120.8(7) . . ?
C26 C25 H25A 119.6 . . ?
C24 C25 H25A 119.6 . . ?
C27 C26 C25 120.9(7) . . ?
C27 C26 H26A 119.5 . . ?
C25 C26 H26A 119.5 . . ?
C28 C27 C26 118.5(7) . . ?
C28 C27 H27A 120.8 . . ?
C26 C27 H27A 120.8 . . ?
C27 C28 C29 121.6(7) . . ?
C27 C28 H28A 119.2 . . ?
C29 C28 H28A 119.2 . . ?
C28 C29 C24 120.2(6) . . ?
C28 C29 H29A 119.9 . . ?
C24 C29 H29A 119.9 . . ?
N4 C30 C31 114.8(4) . . ?
N4 C30 H30B 108.6 . . ?
C31 C30 H30B 108.6 . . ?
N4 C30 H30A 108.6 . . ?
C31 C30 H30A 108.6 . . ?
H30B C30 H30A 107.5 . . ?
C36 C31 C32 118.2(5) . . ?
C36 C31 C30 118.8(4) . . ?
C32 C31 C30 122.9(5) . . ?
C33 C32 C31 120.8(5) . . ?
C33 C32 H32A 119.6 . . ?
C31 C32 H32A 119.6 . . ?
C32 C33 C34 121.2(5) . . ?
C32 C33 H33A 119.4 . . ?
C34 C33 H33A 119.4 . . ?
C33 C34 C35 118.6(5) . . ?
C33 C34 H34A 120.7 . . ?
C35 C34 H34A 120.7 . . ?
C36 C35 C34 119.9(5) . . ?
C36 C35 H35A 120.1 . . ?
C34 C35 H35A 120.1 . . ?
C35 C36 C31 121.3(5) . . ?
C35 C36 H36A 119.3 . . ?
C31 C36 H36A 119.3 . . ?
C1 N1 C3 108.7(4) . . ?
C1 N1 C5 126.6(4) . . ?
C3 N1 C5 124.5(4) . . ?
C1 N2 C4 108.9(4) . . ?
C1 N2 C12 126.9(4) . . ?
C4 N2 C12 123.9(4) . . ?
C19 N3 C21 108.8(5) . . ?
C19 N3 C23 126.9(4) . . ?
C21 N3 C23 124.1(5) . . ?
C19 N4 C22 108.5(4) . . ?
C19 N4 C30 126.3(4) . . ?
C22 N4 C30 125.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.075
#======================================================================
data_i0769
_database_code_depnum_ccdc_archive 'CCDC 847618'
#TrackingRef 'publus88.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N2 S2, C H Cl3'
_chemical_formula_sum            'C13 H15 Cl3 N2 S2'
_chemical_formula_weight         369.74

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   9.1788(10)
_cell_length_b                   14.2940(13)
_cell_length_c                   13.2075(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.883(9)
_cell_angle_gamma                90.00
_cell_volume                     1726.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    218(2)
_cell_measurement_reflns_used    4646
_cell_measurement_theta_min      2.09
_cell_measurement_theta_max      25.50

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8778
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      218(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 126 frames, detector distance = 135 mm
;

_diffrn_standards_decay_%        none
_diffrn_reflns_number            7557
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3028
_reflns_number_gt                1980
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1321P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         3028
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1864
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.7377(4) 0.3501(3) 0.4450(3) 0.0369(9) Uani 1 1 d . . .
C2 C 0.6713(5) 0.2750(3) 0.3765(3) 0.0449(10) Uani 1 1 d . . .
C3 C 0.8508(4) 0.4230(3) 0.5787(3) 0.0376(9) Uani 1 1 d . . .
C4 C 0.9258(5) 0.4480(3) 0.6708(3) 0.0461(10) Uani 1 1 d . . .
H4A H 0.9584 0.4030 0.7194 0.055 Uiso 1 1 calc R . .
C5 C 0.9498(5) 0.5423(4) 0.6871(4) 0.0545(12) Uani 1 1 d . . .
H5A H 1.0000 0.5618 0.7484 0.065 Uiso 1 1 calc R . .
C6 C 0.9018(5) 0.6099(3) 0.6151(4) 0.0547(13) Uani 1 1 d . . .
H6A H 0.9215 0.6734 0.6292 0.066 Uiso 1 1 calc R . .
C7 C 0.8262(5) 0.5858(3) 0.5242(4) 0.0452(10) Uani 1 1 d . . .
H7A H 0.7927 0.6313 0.4764 0.054 Uiso 1 1 calc R . .
C8 C 0.8018(4) 0.4908(3) 0.5065(3) 0.0377(9) Uani 1 1 d . . .
C9 C 0.8377(6) 0.2456(3) 0.5877(4) 0.0496(11) Uani 1 1 d . . .
H9A H 0.9318 0.2482 0.6286 0.060 Uiso 1 1 calc R . .
H9B H 0.8440 0.1966 0.5364 0.060 Uiso 1 1 calc R . .
C10 C 0.7200(7) 0.2208(4) 0.6549(4) 0.0676(14) Uani 1 1 d . . .
H10C H 0.7420 0.1608 0.6870 0.081 Uiso 1 1 calc R . .
H10B H 0.6268 0.2172 0.6145 0.081 Uiso 1 1 calc R . .
H10A H 0.7149 0.2685 0.7068 0.081 Uiso 1 1 calc R . .
C11 C 0.6598(5) 0.4873(3) 0.3327(3) 0.0448(10) Uani 1 1 d . . .
H11B H 0.6422 0.4406 0.2788 0.054 Uiso 1 1 calc R . .
H11A H 0.7251 0.5352 0.3087 0.054 Uiso 1 1 calc R . .
C12 C 0.5164(6) 0.5322(4) 0.3537(4) 0.0613(14) Uani 1 1 d . . .
H12C H 0.4740 0.5629 0.2926 0.074 Uiso 1 1 calc R . .
H12B H 0.5333 0.5779 0.4076 0.074 Uiso 1 1 calc R . .
H12A H 0.4497 0.4845 0.3743 0.074 Uiso 1 1 calc R . .
C13 C 0.2862(8) 0.0853(5) 0.4957(5) 0.0786(17) Uani 1 1 d . . .
H13A H 0.3716 0.1020 0.4584 0.094 Uiso 1 1 calc R . .
N1 N 0.8103(4) 0.3364(2) 0.5363(2) 0.0378(8) Uani 1 1 d . . .
N2 N 0.7314(3) 0.4419(2) 0.4245(3) 0.0366(8) Uani 1 1 d . . .
S1 S 0.49123(15) 0.26324(10) 0.38230(12) 0.0642(4) Uani 1 1 d . . .
S2 S 0.78624(17) 0.21757(9) 0.30750(11) 0.0630(4) Uani 1 1 d . . .
Cl1 Cl 0.2745(2) 0.16547(12) 0.59575(13) 0.0881(6) Uani 1 1 d . . .
Cl2 Cl 0.1295(4) 0.0934(3) 0.4130(2) 0.1898(18) Uani 1 1 d . . .
Cl3 Cl 0.3159(3) -0.02659(12) 0.54976(19) 0.1222(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.039(2) 0.0329(19) 0.040(2) 0.0036(17) 0.0065(17) -0.0022(16)
C2 0.059(3) 0.035(2) 0.040(2) 0.0014(18) -0.002(2) -0.0091(19)
C3 0.034(2) 0.038(2) 0.040(2) -0.0033(17) 0.0065(17) -0.0009(16)
C4 0.040(2) 0.055(3) 0.043(2) -0.008(2) 0.0036(19) -0.0001(19)
C5 0.044(2) 0.067(3) 0.053(3) -0.024(2) 0.002(2) -0.004(2)
C6 0.045(2) 0.047(3) 0.074(3) -0.022(2) 0.012(2) -0.008(2)
C7 0.041(2) 0.035(2) 0.060(3) -0.005(2) 0.012(2) 0.0000(18)
C8 0.0345(19) 0.036(2) 0.043(2) -0.0054(18) 0.0057(17) -0.0033(16)
C9 0.063(3) 0.036(2) 0.048(2) 0.0055(19) -0.005(2) 0.000(2)
C10 0.081(4) 0.062(3) 0.060(3) 0.019(3) 0.000(3) -0.009(3)
C11 0.050(2) 0.046(2) 0.038(2) 0.0122(19) 0.0027(19) 0.0001(19)
C12 0.055(3) 0.074(4) 0.054(3) 0.015(3) -0.002(2) 0.017(3)
C13 0.092(4) 0.072(4) 0.071(4) 0.013(3) 0.005(3) -0.005(3)
N1 0.0408(18) 0.0353(18) 0.0364(17) 0.0028(14) -0.0008(14) -0.0004(14)
N2 0.0366(17) 0.0343(18) 0.0388(18) 0.0014(14) 0.0025(14) -0.0023(14)
S1 0.0518(7) 0.0689(9) 0.0703(9) -0.0065(7) -0.0049(6) -0.0181(6)
S2 0.0775(9) 0.0475(7) 0.0652(8) -0.0174(6) 0.0120(7) -0.0051(6)
Cl1 0.1175(14) 0.0676(10) 0.0810(11) 0.0132(8) 0.0197(10) 0.0074(9)
Cl2 0.169(3) 0.290(5) 0.0968(17) 0.052(2) -0.0664(18) -0.061(3)
Cl3 0.193(2) 0.0505(10) 0.1196(16) 0.0077(10) -0.0104(16) -0.0198(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.340(5) . ?
C1 N1 1.342(5) . ?
C1 C2 1.499(6) . ?
C2 S2 1.668(5) . ?
C2 S1 1.669(5) . ?
C3 C4 1.392(6) . ?
C3 N1 1.396(5) . ?
C3 C8 1.406(6) . ?
C4 C5 1.379(7) . ?
C4 H4A 0.9400 . ?
C5 C6 1.400(8) . ?
C5 H5A 0.9400 . ?
C6 C7 1.378(7) . ?
C6 H6A 0.9400 . ?
C7 C8 1.393(6) . ?
C7 H7A 0.9400 . ?
C8 N2 1.401(5) . ?
C9 N1 1.476(5) . ?
C9 C10 1.498(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10C 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10A 0.9700 . ?
C11 N2 1.479(5) . ?
C11 C12 1.511(7) . ?
C11 H11B 0.9800 . ?
C11 H11A 0.9800 . ?
C12 H12C 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 Cl2 1.735(8) . ?
C13 Cl1 1.759(7) . ?
C13 Cl3 1.763(7) . ?
C13 H13A 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
N2 C1 N1 109.5(4) . . ?
N2 C1 C2 124.8(4) . . ?
N1 C1 C2 125.7(4) . . ?
C1 C2 S2 116.0(3) . . ?
C1 C2 S1 113.4(3) . . ?
S2 C2 S1 130.6(3) . . ?
C4 C3 N1 132.3(4) . . ?
C4 C3 C8 121.4(4) . . ?
N1 C3 C8 106.3(3) . . ?
C5 C4 C3 116.6(5) . . ?
C5 C4 H4A 121.7 . . ?
C3 C4 H4A 121.7 . . ?
C4 C5 C6 122.1(5) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C8 116.9(5) . . ?
C6 C7 H7A 121.6 . . ?
C8 C7 H7A 121.6 . . ?
C7 C8 N2 132.4(4) . . ?
C7 C8 C3 121.4(4) . . ?
N2 C8 C3 106.3(3) . . ?
N1 C9 C10 112.1(4) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10C 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
N2 C11 C12 111.7(3) . . ?
N2 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
N2 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
H11B C11 H11A 107.9 . . ?
C11 C12 H12C 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
Cl2 C13 Cl1 109.2(4) . . ?
Cl2 C13 Cl3 114.0(4) . . ?
Cl1 C13 Cl3 107.7(4) . . ?
Cl2 C13 H13A 108.6 . . ?
Cl1 C13 H13A 108.6 . . ?
Cl3 C13 H13A 108.6 . . ?
C1 N1 C3 109.0(3) . . ?
C1 N1 C9 126.4(4) . . ?
C3 N1 C9 124.5(3) . . ?
C1 N2 C8 108.9(3) . . ?
C1 N2 C11 127.2(4) . . ?
C8 N2 C11 123.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.212
#======================================================================