# 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        'Heidi Saxell'
_publ_contact_author_email       HEIDI.SAXELL@BASF.COM

_publ_section_title              
;
Polymorphism and versatile solvate formation of thiophanate-methyl
;
loop_
_publ_author_name
'Heidi Saxell'
'Erkki Kolehmainen'
'Elisa Nauha'
'Maija Nissinen'
'Ansgar Schafer'
;
R.Schlecker
;

# Attachment 'B905511H.cif'

data_TM_formI
_database_code_depnum_ccdc_archive 'CCDC 724460'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            thiophanate-methyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2'
_chemical_formula_sum            'C12 H14 N4 O4 S2'
_chemical_formula_weight         342.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   10.7149(5)
_cell_length_b                   11.8405(5)
_cell_length_c                   15.6861(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 132.593(2)
_cell_angle_gamma                90.00
_cell_volume                     1465.06(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    3.532
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_T_max  0.5385
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9506
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.35
_diffrn_reflns_theta_max         54.86
_reflns_number_total             1744
_reflns_number_gt                1620
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91 Å
to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0483P)²+3.0780P] 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     SHELXL
_refine_ls_extinction_coef       0.0067(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1744
_refine_ls_number_parameters     214
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.05783(12) 0.97077(8) 0.38905(8) 0.0222(4) Uani 1 1 d . . .
S2 S 0.81503(12) 0.86570(8) 0.74422(8) 0.0252(4) Uani 1 1 d . . .
O1 O 0.0845(3) 0.6392(2) 0.5512(2) 0.0222(7) Uani 1 1 d . . .
O2 O -0.1068(3) 0.7291(2) 0.5459(2) 0.0256(7) Uani 1 1 d . . .
O3 O 0.3561(3) 1.0053(2) 0.6746(2) 0.0268(7) Uani 1 1 d . . .
O4 O 0.5598(3) 1.0563(2) 0.8618(2) 0.0251(7) Uani 1 1 d . . .
N1 N -0.0054(4) 0.8212(3) 0.4813(3) 0.0195(8) Uani 1 1 d D . .
H1 H -0.062(4) 0.879(2) 0.479(3) 0.023 Uiso 1 1 d D . .
N2 N 0.1878(4) 0.7649(3) 0.4684(3) 0.0180(8) Uani 1 1 d D . .
H2 H 0.189(5) 0.696(2) 0.495(3) 0.022 Uiso 1 1 d D . .
N3 N 0.4772(4) 0.8990(3) 0.5933(3) 0.0198(8) Uani 1 1 d D . .
H3 H 0.392(4) 0.933(3) 0.581(3) 0.024 Uiso 1 1 d D . .
N4 N 0.6380(4) 0.9786(3) 0.7753(3) 0.0213(8) Uani 1 1 d D . .
H4 H 0.744(3) 0.992(3) 0.842(2) 0.026 Uiso 1 1 d D . .
C1 C -0.1115(6) 0.6312(3) 0.6000(4) 0.0288(10) Uani 1 1 d . . .
H1A H -0.1624 0.5672 0.5462 0.043 Uiso 1 1 calc R . .
H1B H -0.1793 0.6490 0.6192 0.043 Uiso 1 1 calc R . .
H1C H 0.0042 0.6117 0.6708 0.043 Uiso 1 1 calc R . .
C2 C -0.0018(5) 0.7206(4) 0.5285(3) 0.0213(10) Uani 1 1 d . . .
C3 C 0.0833(5) 0.8455(3) 0.4486(3) 0.0194(9) Uani 1 1 d . . .
C4 C 0.2815(5) 0.7729(3) 0.4333(3) 0.0197(9) Uani 1 1 d . . .
C5 C 0.2291(5) 0.7100(3) 0.3393(3) 0.0231(10) Uani 1 1 d . . .
H5 H 0.1275 0.6671 0.2957 0.028 Uiso 1 1 calc R . .
C6 C 0.3235(5) 0.7092(3) 0.3086(3) 0.0251(10) Uani 1 1 d . . .
H6 H 0.2867 0.6664 0.2438 0.030 Uiso 1 1 calc R . .
C7 C 0.4733(5) 0.7718(3) 0.3737(3) 0.0237(10) Uani 1 1 d . . .
H7 H 0.5398 0.7705 0.3539 0.028 Uiso 1 1 calc R . .
C8 C 0.5251(5) 0.8356(3) 0.4668(3) 0.0215(9) Uani 1 1 d . . .
H8 H 0.6257 0.8794 0.5096 0.026 Uiso 1 1 calc R . .
C9 C 0.4309(5) 0.8361(3) 0.4984(3) 0.0196(9) Uani 1 1 d . . .
C10 C 0.6334(5) 0.9148(3) 0.6974(3) 0.0202(9) Uani 1 1 d . . .
C11 C 0.5039(5) 1.0131(3) 0.7618(3) 0.0216(9) Uani 1 1 d . . .
C12 C 0.4236(5) 1.0903(4) 0.8565(4) 0.0275(10) Uani 1 1 d . . .
H12A H 0.3682 1.1583 0.8086 0.041 Uiso 1 1 calc R . .
H12B H 0.4709 1.1063 0.9349 0.041 Uiso 1 1 calc R . .
H12C H 0.3403 1.0292 0.8225 0.041 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
S1 C3 1.674(4) . ?
S2 C10 1.652(4) . ?
O1 C2 1.210(5) . ?
O2 C2 1.329(5) . ?
O2 C1 1.457(5) . ?
O3 C11 1.207(5) . ?
O4 C11 1.345(5) . ?
O4 C12 1.462(5) . ?
N1 C3 1.382(5) . ?
N1 C2 1.389(5) . ?
N1 H1 0.900(19) . ?
N2 C3 1.339(5) . ?
N2 C4 1.437(5) . ?
N2 H2 0.903(19) . ?
N3 C10 1.343(5) . ?
N3 C9 1.420(5) . ?
N3 H3 0.896(19) . ?
N4 C11 1.365(5) . ?
N4 C10 1.409(5) . ?
N4 H4 0.90(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.387(5) . ?
C4 C9 1.397(5) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(5) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C2 O2 C1 115.3(3) . . ?
C11 O4 C12 113.5(3) . . ?
C3 N1 C2 126.7(3) . . ?
C3 N1 H1 116(3) . . ?
C2 N1 H1 117(3) . . ?
C3 N2 C4 123.7(3) . . ?
C3 N2 H2 120(2) . . ?
C4 N2 H2 115(2) . . ?
C10 N3 C9 127.7(3) . . ?
C10 N3 H3 117(3) . . ?
C9 N3 H3 116(3) . . ?
C11 N4 C10 127.6(3) . . ?
C11 N4 H4 120(3) . . ?
C10 N4 H4 112(3) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 125.7(4) . . ?
O1 C2 N1 125.5(3) . . ?
O2 C2 N1 108.8(3) . . ?
N2 C3 N1 116.3(3) . . ?
N2 C3 S1 123.8(3) . . ?
N1 C3 S1 119.9(3) . . ?
C5 C4 C9 120.2(3) . . ?
C5 C4 N2 119.1(3) . . ?
C9 C4 N2 120.5(3) . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.1(3) . . ?
C8 C9 N3 123.5(3) . . ?
C4 C9 N3 117.4(3) . . ?
N3 C10 N4 114.4(3) . . ?
N3 C10 S2 128.0(3) . . ?
N4 C10 S2 117.6(3) . . ?
O3 C11 O4 123.9(4) . . ?
O3 C11 N4 126.1(3) . . ?
O4 C11 N4 110.0(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 1.7(5) . . . . ?
C1 O2 C2 N1 -177.5(3) . . . . ?
C3 N1 C2 O1 2.2(6) . . . . ?
C3 N1 C2 O2 -178.6(3) . . . . ?
C4 N2 C3 N1 175.9(3) . . . . ?
C4 N2 C3 S1 -4.6(5) . . . . ?
C2 N1 C3 N2 -2.5(5) . . . . ?
C2 N1 C3 S1 178.0(3) . . . . ?
C3 N2 C4 C5 -105.5(4) . . . . ?
C3 N2 C4 C9 79.6(5) . . . . ?
C9 C4 C5 C6 -0.2(6) . . . . ?
N2 C4 C5 C6 -175.1(3) . . . . ?
C4 C5 C6 C7 0.4(6) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C8 C9 C4 -1.2(5) . . . . ?
C7 C8 C9 N3 179.6(3) . . . . ?
C5 C4 C9 C8 0.5(5) . . . . ?
N2 C4 C9 C8 175.4(3) . . . . ?
C5 C4 C9 N3 179.8(3) . . . . ?
N2 C4 C9 N3 -5.3(5) . . . . ?
C10 N3 C9 C8 -39.2(6) . . . . ?
C10 N3 C9 C4 141.6(4) . . . . ?
C9 N3 C10 N4 -178.0(3) . . . . ?
C9 N3 C10 S2 -0.1(6) . . . . ?
C11 N4 C10 N3 8.4(5) . . . . ?
C11 N4 C10 S2 -169.7(3) . . . . ?
C12 O4 C11 O3 1.8(5) . . . . ?
C12 O4 C11 N4 -177.1(3) . . . . ?
C10 N4 C11 O3 -8.7(6) . . . . ?
C10 N4 C11 O4 170.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.900(19) 2.70(3) 3.473(3) 144(3) 3_576
N2 H2 O1 0.903(19) 1.97(3) 2.660(4) 132(3) .
N2 H2 O4 0.903(19) 2.62(3) 3.280(4) 131(3) 2_646
N3 H3 O3 0.896(19) 1.94(3) 2.671(4) 137(3) .
N3 H3 S1 0.896(19) 2.74(3) 3.419(3) 134(3) .
N4 H4 O1 0.90(2) 2.25(3) 2.985(4) 139(3) 2_656

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        54.86
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.078

data_TM_formII
_database_code_depnum_ccdc_archive 'CCDC 724461'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            thiophanate-methyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2'
_chemical_formula_sum            'C12 H14 N4 O4 S2'
_chemical_formula_weight         342.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p2(1)/c

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                   8.9524(18)
_cell_length_b                   20.073(4)
_cell_length_c                   8.9959(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.48(3)
_cell_angle_gamma                90.00
_cell_volume                     1541.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    3.356
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5834
_exptl_absorpt_correction_T_max  0.6889
_exptl_absorpt_process_details   
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD Apex II detector'
_diffrn_measurement_method       'psi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2657
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         66.82
_reflns_number_total             2657
_reflns_number_gt                2371
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS, 2004)'
_computing_cell_refinement       Denzo
_computing_data_reduction        Denzo
_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 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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0614P)²+1.0354P] 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         2657
_refine_ls_number_parameters     213
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.22538(7) 0.63460(3) 0.25773(7) 0.0372(2) Uani 1 1 d . . .
S1 S -0.57951(7) 0.67693(3) -0.12234(7) 0.0372(2) Uani 1 1 d . . .
N1 N -0.4737(2) 0.78949(9) 0.0216(2) 0.0328(4) Uani 1 1 d D . .
H1 H -0.557(2) 0.8075(13) -0.046(3) 0.039 Uiso 1 1 d D . .
N2 N -0.3321(2) 0.69565(9) 0.1256(2) 0.0312(4) Uani 1 1 d D . .
H2 H -0.269(3) 0.7245(12) 0.190(3) 0.037 Uiso 1 1 d D . .
N3 N -0.0562(2) 0.66903(9) 0.0672(2) 0.0291(4) Uani 1 1 d D . .
H3 H -0.115(3) 0.7005(11) 0.006(3) 0.035 Uiso 1 1 d D . .
N4 N 0.1351(2) 0.74940(10) 0.1186(2) 0.0336(4) Uani 1 1 d D . .
H4 H 0.228(2) 0.7604(14) 0.181(3) 0.040 Uiso 1 1 d D . .
O1 O -0.2590(2) 0.82140(8) 0.2232(2) 0.0418(4) Uani 1 1 d . . .
O2 O -0.4331(2) 0.89618(8) 0.0825(2) 0.0387(4) Uani 1 1 d . . .
O3 O -0.0908(2) 0.79289(8) -0.0485(2) 0.0406(4) Uani 1 1 d . . .
O4 O 0.1064(2) 0.85820(8) 0.0906(2) 0.0417(4) Uani 1 1 d . . .
C1 C -0.3494(3) 0.94835(13) 0.1849(3) 0.0455(6) Uani 1 1 d . . .
H1A H -0.3595 0.9417 0.2894 0.068 Uiso 1 1 calc R . .
H1B H -0.3935 0.9917 0.1445 0.068 Uiso 1 1 calc R . .
H1C H -0.2385 0.9469 0.1903 0.068 Uiso 1 1 calc R . .
C2 C -0.3771(3) 0.83477(12) 0.1205(3) 0.0335(5) Uani 1 1 d . . .
C3 C -0.4537(3) 0.72156(11) 0.0166(3) 0.0289(5) Uani 1 1 d . . .
C4 C -0.2846(3) 0.62758(11) 0.1256(3) 0.0288(5) Uani 1 1 d . . .
C5 C -0.3754(3) 0.57580(12) 0.1540(3) 0.0365(5) Uani 1 1 d . . .
H5 H -0.4716 0.5851 0.1741 0.044 Uiso 1 1 calc R . .
C6 C -0.3251(3) 0.51066(12) 0.1528(3) 0.0375(6) Uani 1 1 d . . .
H6 H -0.3876 0.4751 0.1708 0.045 Uiso 1 1 calc R . .
C7 C -0.1844(3) 0.49723(11) 0.1256(3) 0.0340(5) Uani 1 1 d . . .
H7 H -0.1508 0.4524 0.1242 0.041 Uiso 1 1 calc R . .
C8 C -0.0916(3) 0.54873(10) 0.1001(3) 0.0303(5) Uani 1 1 d . . .
H8 H 0.0060 0.5392 0.0831 0.036 Uiso 1 1 calc R . .
C9 C -0.1419(2) 0.61423(10) 0.0996(2) 0.0264(5) Uani 1 1 d . . .
C10 C 0.0927(3) 0.68493(11) 0.1411(3) 0.0280(5) Uani 1 1 d . . .
C11 C 0.0375(3) 0.80002(11) 0.0442(3) 0.0321(5) Uani 1 1 d . . .
C12 C 0.0190(4) 0.91646(12) 0.0198(3) 0.0455(7) Uani 1 1 d . . .
H12A H -0.0006 0.9147 -0.0933 0.068 Uiso 1 1 calc R . .
H12B H 0.0793 0.9566 0.0616 0.068 Uiso 1 1 calc R . .
H12C H -0.0811 0.9176 0.0432 0.068 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
S2 C10 1.668(2) . ?
S1 C3 1.670(2) . ?
N1 C3 1.378(3) . ?
N1 C2 1.380(3) . ?
N1 H1 0.883(17) . ?
N2 C3 1.333(3) . ?
N2 C4 1.431(3) . ?
N2 H2 0.892(17) . ?
N3 C10 1.338(3) . ?
N3 C9 1.421(3) . ?
N3 H3 0.896(17) . ?
N4 C11 1.376(3) . ?
N4 C10 1.380(3) . ?
N4 H4 0.882(17) . ?
O1 C2 1.207(3) . ?
O2 C2 1.336(3) . ?
O2 C1 1.446(3) . ?
O3 C11 1.209(3) . ?
O4 C11 1.328(3) . ?
O4 C12 1.444(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.390(3) . ?
C4 C9 1.392(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C3 N1 C2 127.6(2) . . ?
C3 N1 H1 118.2(19) . . ?
C2 N1 H1 114.2(18) . . ?
C3 N2 C4 123.34(19) . . ?
C3 N2 H2 116.4(18) . . ?
C4 N2 H2 119.2(18) . . ?
C10 N3 C9 126.99(19) . . ?
C10 N3 H3 116.7(17) . . ?
C9 N3 H3 114.7(17) . . ?
C11 N4 C10 127.0(2) . . ?
C11 N4 H4 117.8(19) . . ?
C10 N4 H4 113.0(19) . . ?
C2 O2 C1 114.99(19) . . ?
C11 O4 C12 115.76(19) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 125.2(2) . . ?
O1 C2 N1 125.6(2) . . ?
O2 C2 N1 109.16(19) . . ?
N2 C3 N1 116.6(2) . . ?
N2 C3 S1 124.03(17) . . ?
N1 C3 S1 119.37(17) . . ?
C5 C4 C9 120.3(2) . . ?
C5 C4 N2 121.6(2) . . ?
C9 C4 N2 118.2(2) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 119.7(2) . . ?
C8 C9 N3 122.6(2) . . ?
C4 C9 N3 117.70(19) . . ?
N3 C10 N4 115.30(19) . . ?
N3 C10 S2 125.68(17) . . ?
N4 C10 S2 119.01(17) . . ?
O3 C11 O4 125.2(2) . . ?
O3 C11 N4 125.6(2) . . ?
O4 C11 N4 109.3(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 -5.9(4) . . . . ?
C1 O2 C2 N1 175.5(2) . . . . ?
C3 N1 C2 O1 -1.9(4) . . . . ?
C3 N1 C2 O2 176.7(2) . . . . ?
C4 N2 C3 N1 -172.4(2) . . . . ?
C4 N2 C3 S1 7.5(3) . . . . ?
C2 N1 C3 N2 4.3(4) . . . . ?
C2 N1 C3 S1 -175.52(19) . . . . ?
C3 N2 C4 C5 -69.1(3) . . . . ?
C3 N2 C4 C9 112.3(2) . . . . ?
C9 C4 C5 C6 -1.5(3) . . . . ?
N2 C4 C5 C6 180.0(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C7 C8 C9 N3 -177.0(2) . . . . ?
C5 C4 C9 C8 0.8(3) . . . . ?
N2 C4 C9 C8 179.45(19) . . . . ?
C5 C4 C9 N3 178.4(2) . . . . ?
N2 C4 C9 N3 -3.0(3) . . . . ?
C10 N3 C9 C8 -56.2(3) . . . . ?
C10 N3 C9 C4 126.3(2) . . . . ?
C9 N3 C10 N4 -162.3(2) . . . . ?
C9 N3 C10 S2 16.3(3) . . . . ?
C11 N4 C10 N3 7.9(3) . . . . ?
C11 N4 C10 S2 -170.85(19) . . . . ?
C12 O4 C11 O3 -1.4(4) . . . . ?
C12 O4 C11 N4 178.8(2) . . . . ?
C10 N4 C11 O3 -21.2(4) . . . . ?
C10 N4 C11 O4 158.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S2 0.883(17) 2.492(18) 3.372(2) 175(2) 4_475
N2 H2 O1 0.892(17) 1.97(2) 2.688(3) 137(2) .
N2 H2 O3 0.892(17) 2.44(2) 3.084(3) 130(2) 4_576
N3 H3 O3 0.896(17) 1.95(2) 2.677(2) 137(2) .
N3 H3 O1 0.896(17) 2.52(2) 3.088(3) 122(2) 4_575
N4 H4 S1 0.882(17) 2.419(19) 3.251(2) 157(2) 4_676

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        66.82
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.057

data_TM_MeCN_H2O
_database_code_depnum_ccdc_archive 'CCDC 724462'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl,acetonitrile monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C12 H14 N4 O4 S2), 2.5(C2 H3 N), H2 O'
_chemical_formula_sum            'C41 H51.50 N14.50 O13 S6'
_chemical_formula_weight         1147.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.641(2)
_cell_length_b                   13.751(3)
_cell_length_c                   20.181(4)
_cell_angle_alpha                74.62(3)
_cell_angle_beta                 85.49(3)
_cell_angle_gamma                77.97(3)
_cell_volume                     2783.7(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1198
_exptl_absorpt_coefficient_mu    2.874
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_T_max  0.8696
_exptl_absorpt_process_details   
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD Apex II detector'
_diffrn_measurement_method       'psi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9429
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         66.81
_reflns_number_total             9429
_reflns_number_gt                6642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS, 2004)'
_computing_cell_refinement       Denzo
_computing_data_reduction        Denzo
_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 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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0854P)²+6.7133P] 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         9429
_refine_ls_number_parameters     730
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2014
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.05105(12) 0.86433(11) 0.36474(7) 0.0444(3) Uani 1 1 d . . .
S2 S 0.41370(18) 0.72433(14) 0.48997(9) 0.0739(5) Uani 1 1 d . . .
O1 O 0.3439(3) 0.7305(3) 0.2873(2) 0.0552(11) Uani 1 1 d . . .
O2 O 0.2267(3) 0.6434(3) 0.24388(19) 0.0461(9) Uani 1 1 d . . .
O3 O 0.0197(7) 0.6497(5) 0.5488(3) 0.0993(18) Uani 1 1 d . . .
O4 O 0.1371(8) 0.4881(4) 0.5788(3) 0.115(2) Uani 1 1 d . . .
N1 N 0.1236(4) 0.7569(3) 0.2989(2) 0.0371(9) Uani 1 1 d D . .
H1N H 0.054(3) 0.739(4) 0.286(3) 0.045 Uiso 1 1 d D . .
N2 N 0.2003(4) 0.8573(3) 0.3553(2) 0.0368(9) Uani 1 1 d D . .
H2N H 0.280(3) 0.827(4) 0.344(3) 0.044 Uiso 1 1 d D . .
N3 N 0.1622(5) 0.7928(4) 0.5000(2) 0.0504(11) Uani 1 1 d D . .
H3N H 0.080(3) 0.786(5) 0.513(3) 0.061 Uiso 1 1 d D . .
N4 N 0.2399(7) 0.6178(4) 0.5407(3) 0.0794(17) Uani 1 1 d D . .
H4N H 0.308(5) 0.564(4) 0.556(4) 0.095 Uiso 1 1 d D . .
C1 C 0.3434(6) 0.5907(5) 0.2169(4) 0.0639(18) Uani 1 1 d . . .
H1A H 0.3762 0.6385 0.1775 0.096 Uiso 1 1 calc R . .
H1B H 0.3250 0.5327 0.2022 0.096 Uiso 1 1 calc R . .
H1C H 0.4079 0.5652 0.2527 0.096 Uiso 1 1 calc R . .
C2 C 0.2420(5) 0.7117(4) 0.2773(3) 0.0420(12) Uani 1 1 d . . .
C3 C 0.0998(4) 0.8262(4) 0.3387(2) 0.0347(11) Uani 1 1 d . . .
C4 C 0.1883(4) 0.9289(4) 0.3970(2) 0.0355(11) Uani 1 1 d . . .
C5 C 0.1942(5) 1.0300(4) 0.3661(3) 0.0417(12) Uani 1 1 d . . .
H5 H 0.2046 1.0521 0.3175 0.050 Uiso 1 1 calc R . .
C6 C 0.1849(5) 1.0997(4) 0.4058(3) 0.0488(13) Uani 1 1 d . . .
H6 H 0.1897 1.1693 0.3846 0.059 Uiso 1 1 calc R . .
C7 C 0.1688(5) 1.0677(4) 0.4759(3) 0.0452(13) Uani 1 1 d . . .
H7 H 0.1625 1.1154 0.5031 0.054 Uiso 1 1 calc R . .
C8 C 0.1616(5) 0.9669(4) 0.5070(3) 0.0423(12) Uani 1 1 d . . .
H8 H 0.1490 0.9453 0.5554 0.051 Uiso 1 1 calc R . .
C9 C 0.1730(5) 0.8966(4) 0.4672(3) 0.0390(11) Uani 1 1 d . . .
C10 C 0.2677(7) 0.7123(5) 0.5099(3) 0.0623(18) Uani 1 1 d . . .
C11 C 0.1250(11) 0.5924(7) 0.5540(4) 0.088(2) Uani 1 1 d . . .
C12 C 0.0160(13) 0.4500(8) 0.5976(5) 0.139(5) Uani 1 1 d . . .
H12A H -0.0105 0.4538 0.6446 0.208 Uiso 1 1 calc R . .
H12B H 0.0291 0.3785 0.5948 0.208 Uiso 1 1 calc R . .
H12C H -0.0510 0.4925 0.5658 0.208 Uiso 1 1 calc R . .
S3 S 0.86423(12) 0.72311(12) 0.21978(7) 0.0490(4) Uani 1 1 d . . .
S4 S 0.22925(11) 0.89017(10) 0.11975(8) 0.0450(3) Uani 1 1 d . . .
O5 O 0.4901(3) 0.8842(3) 0.30497(19) 0.0479(9) Uani 1 1 d . . .
O6 O 0.6287(3) 0.8907(3) 0.38209(18) 0.0455(9) Uani 1 1 d . . .
O7 O 0.4892(3) 1.0850(3) 0.1714(2) 0.0462(9) Uani 1 1 d . . .
O8 O 0.3003(3) 1.1589(2) 0.21189(17) 0.0373(8) Uani 1 1 d . . .
N5 N 0.7036(4) 0.8054(3) 0.3046(2) 0.0397(10) Uani 1 1 d D . .
H5N H 0.779(3) 0.801(4) 0.325(3) 0.048 Uiso 1 1 d D . .
N6 N 0.6078(4) 0.7755(3) 0.2149(2) 0.0377(9) Uani 1 1 d D . .
H6N H 0.533(3) 0.800(4) 0.235(2) 0.045 Uiso 1 1 d D . .
N7 N 0.4640(4) 0.9284(3) 0.1203(2) 0.0375(10) Uani 1 1 d D . .
H7N H 0.507(4) 0.976(3) 0.124(3) 0.045 Uiso 1 1 d D . .
N8 N 0.2983(3) 1.0398(3) 0.1579(2) 0.0360(9) Uani 1 1 d D . .
H8N H 0.213(2) 1.056(4) 0.166(3) 0.043 Uiso 1 1 d D . .
C13 C 0.5270(5) 0.9565(5) 0.4111(3) 0.0553(15) Uani 1 1 d . . .
H13A H 0.4851 1.0130 0.3742 0.083 Uiso 1 1 calc R . .
H13B H 0.5637 0.9846 0.4434 0.083 Uiso 1 1 calc R . .
H13C H 0.4637 0.9163 0.4355 0.083 Uiso 1 1 calc R . .
C14 C 0.5959(5) 0.8626(4) 0.3287(3) 0.0385(11) Uani 1 1 d . . .
C15 C 0.7166(4) 0.7693(4) 0.2459(2) 0.0358(11) Uani 1 1 d . . .
C16 C 0.5978(4) 0.7583(4) 0.1497(3) 0.0356(11) Uani 1 1 d . . .
C17 C 0.6556(5) 0.6676(4) 0.1323(3) 0.0427(12) Uani 1 1 d . . .
H17 H 0.7058 0.6132 0.1648 0.051 Uiso 1 1 calc R . .
C18 C 0.6391(5) 0.6575(4) 0.0675(3) 0.0493(14) Uani 1 1 d . . .
H18 H 0.6790 0.5958 0.0554 0.059 Uiso 1 1 calc R . .
C19 C 0.5658(5) 0.7352(5) 0.0199(3) 0.0503(14) Uani 1 1 d . . .
H19 H 0.5562 0.7270 -0.0246 0.060 Uiso 1 1 calc R . .
C20 C 0.5065(5) 0.8244(5) 0.0366(3) 0.0462(13) Uani 1 1 d . . .
H20 H 0.4552 0.8779 0.0041 0.055 Uiso 1 1 calc R . .
C21 C 0.5225(4) 0.8355(4) 0.1016(3) 0.0371(11) Uani 1 1 d . . .
C22 C 0.3381(4) 0.9539(4) 0.1327(2) 0.0354(11) Uani 1 1 d . . .
C23 C 0.3746(4) 1.0941(4) 0.1796(2) 0.0350(11) Uani 1 1 d . . .
C24 C 0.3670(5) 1.2187(4) 0.2410(3) 0.0439(13) Uani 1 1 d . . .
H24A H 0.4288 1.1723 0.2744 0.066 Uiso 1 1 calc R . .
H24B H 0.3048 1.2631 0.2641 0.066 Uiso 1 1 calc R . .
H24C H 0.4127 1.2613 0.2043 0.066 Uiso 1 1 calc R . .
S5 S 1.00110(11) 0.12123(11) 0.20517(7) 0.0439(3) Uani 1 1 d . . .
S6 S 0.47628(11) 0.42859(10) 0.10354(6) 0.0396(3) Uani 1 1 d . . .
O9 O 0.7282(3) -0.0174(3) 0.11035(19) 0.0426(8) Uani 1 1 d . . .
O10 O 0.9144(3) -0.0844(3) 0.06306(17) 0.0382(8) Uani 1 1 d . . .
O11 O 0.8641(3) 0.2721(3) 0.02947(18) 0.0458(9) Uani 1 1 d . . .
O12 O 0.8031(3) 0.3903(3) -0.06950(17) 0.0439(9) Uani 1 1 d . . .
N9 N 0.9246(4) 0.0058(3) 0.1367(2) 0.0372(9) Uani 1 1 d D . .
H9N H 1.009(2) -0.019(4) 0.130(3) 0.045 Uiso 1 1 d D . .
N10 N 0.7651(4) 0.0945(3) 0.1958(2) 0.0324(9) Uani 1 1 d D . .
H10N H 0.708(4) 0.067(4) 0.180(2) 0.039 Uiso 1 1 d D . .
N11 N 0.7033(4) 0.3020(3) 0.1335(2) 0.0376(10) Uani 1 1 d D . .
H11N H 0.780(3) 0.271(4) 0.117(3) 0.045 Uiso 1 1 d D . .
N12 N 0.6727(4) 0.3898(3) 0.0206(2) 0.0367(9) Uani 1 1 d D . .
H12N H 0.623(4) 0.436(3) -0.012(2) 0.044 Uiso 1 1 d D . .
C25 C 0.8441(5) -0.1298(4) 0.0243(3) 0.0434(12) Uani 1 1 d . . .
H25A H 0.8035 -0.1823 0.0561 0.065 Uiso 1 1 calc R . .
H25B H 0.9035 -0.1614 -0.0071 0.065 Uiso 1 1 calc R . .
H25C H 0.7778 -0.0762 -0.0022 0.065 Uiso 1 1 calc R . .
C26 C 0.8441(4) -0.0324(4) 0.1040(2) 0.0347(11) Uani 1 1 d . . .
C27 C 0.8892(4) 0.0716(3) 0.1788(2) 0.0326(10) Uani 1 1 d . . .
C28 C 0.7169(4) 0.1649(4) 0.2371(2) 0.0316(10) Uani 1 1 d . . .
C29 C 0.7038(5) 0.1296(4) 0.3072(3) 0.0400(12) Uani 1 1 d . . .
H29 H 0.7311 0.0586 0.3288 0.048 Uiso 1 1 calc R . .
C30 C 0.6507(5) 0.1977(4) 0.3464(3) 0.0437(12) Uani 1 1 d . . .
H30 H 0.6402 0.1732 0.3948 0.052 Uiso 1 1 calc R . .
C31 C 0.6130(5) 0.3013(4) 0.3152(3) 0.0442(13) Uani 1 1 d . . .
H31 H 0.5761 0.3477 0.3422 0.053 Uiso 1 1 calc R . .
C32 C 0.6288(5) 0.3376(4) 0.2451(3) 0.0389(11) Uani 1 1 d . . .
H32 H 0.6045 0.4090 0.2238 0.047 Uiso 1 1 calc R . .
C33 C 0.6809(4) 0.2687(4) 0.2055(2) 0.0319(10) Uani 1 1 d . . .
C34 C 0.6248(4) 0.3691(3) 0.0873(2) 0.0325(10) Uani 1 1 d . . .
C35 C 0.7880(5) 0.3437(4) -0.0037(3) 0.0375(11) Uani 1 1 d . . .
C36 C 0.9185(5) 0.3469(4) -0.1034(3) 0.0477(14) Uani 1 1 d . . .
H36A H 0.9945 0.3507 -0.0804 0.072 Uiso 1 1 calc R . .
H36B H 0.9211 0.3859 -0.1517 0.072 Uiso 1 1 calc R . .
H36C H 0.9179 0.2749 -0.1011 0.072 Uiso 1 1 calc R . .
N100 N -0.0930(6) 0.4663(5) 0.0910(4) 0.090(2) Uani 1 1 d . . .
C100 C 0.0056(6) 0.4167(5) 0.0882(3) 0.0583(16) Uani 1 1 d . . .
C101 C 0.1300(6) 0.3545(5) 0.0839(4) 0.075(2) Uani 1 1 d . . .
H10A H 0.1511 0.3535 0.0359 0.112 Uiso 1 1 calc R . .
H10B H 0.1302 0.2842 0.1117 0.112 Uiso 1 1 calc R . .
H10C H 0.1941 0.3830 0.1011 0.112 Uiso 1 1 calc R . .
N200 N 1.1360(8) 0.4120(7) 0.2696(7) 0.148(4) Uani 1 1 d . . .
C200 C 1.0345(9) 0.3992(8) 0.2722(5) 0.099(3) Uani 1 1 d . . .
C201 C 0.9065(10) 0.3797(13) 0.2760(7) 0.171(6) Uani 1 1 d . . .
H20A H 0.9077 0.3069 0.2983 0.257 Uiso 1 1 calc R . .
H20B H 0.8735 0.3964 0.2295 0.257 Uiso 1 1 calc R . .
H20C H 0.8508 0.4223 0.3028 0.257 Uiso 1 1 calc R . .
N300 N 0.3176(15) 0.5007(14) 0.4040(7) 0.101(5) Uani 0.50 1 d P . .
C300 C 0.2991(16) 0.4281(14) 0.4258(12) 0.093(6) Uani 0.50 1 d P . .
C301 C 0.2758(14) 0.3229(11) 0.4656(12) 0.114(8) Uani 0.50 1 d P . .
H30A H 0.3468 0.2698 0.4563 0.171 Uiso 0.50 1 calc PR . .
H30B H 0.1949 0.3120 0.4513 0.171 Uiso 0.50 1 calc PR . .
H30C H 0.2705 0.3190 0.5149 0.171 Uiso 0.50 1 calc PR . .
O400 O 0.5517(10) 0.5451(6) 0.4040(5) 0.183(4) 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
S1 C3 1.671(5) . ?
S2 C10 1.605(8) . ?
O1 C2 1.209(6) . ?
O2 C2 1.334(6) . ?
O2 C1 1.446(6) . ?
O3 C11 1.223(11) . ?
O4 C11 1.369(10) . ?
O4 C12 1.475(13) . ?
N1 C2 1.376(6) . ?
N1 C3 1.376(6) . ?
N2 C3 1.327(6) . ?
N2 C4 1.437(6) . ?
N3 C10 1.388(8) . ?
N3 C9 1.429(7) . ?
N4 C11 1.328(11) . ?
N4 C10 1.366(9) . ?
C4 C9 1.375(7) . ?
C4 C5 1.377(7) . ?
C5 C6 1.388(7) . ?
C6 C7 1.373(8) . ?
C7 C8 1.377(8) . ?
C8 C9 1.394(7) . ?
S3 C15 1.668(5) . ?
S4 C22 1.664(5) . ?
O5 C14 1.206(6) . ?
O6 C14 1.329(6) . ?
O6 C13 1.451(6) . ?
O7 C23 1.202(6) . ?
O8 C23 1.333(5) . ?
O8 C24 1.446(6) . ?
N5 C14 1.382(6) . ?
N5 C15 1.386(6) . ?
N6 C15 1.337(6) . ?
N6 C16 1.413(6) . ?
N7 C22 1.334(6) . ?
N7 C21 1.432(6) . ?
N8 C23 1.376(6) . ?
N8 C22 1.382(6) . ?
C16 C21 1.390(7) . ?
C16 C17 1.391(7) . ?
C17 C18 1.381(8) . ?
C18 C19 1.378(8) . ?
C19 C20 1.371(7) . ?
C20 C21 1.386(7) . ?
S5 C27 1.672(5) . ?
S6 C34 1.672(5) . ?
O9 C26 1.209(5) . ?
O10 C26 1.323(5) . ?
O10 C25 1.451(6) . ?
O11 C35 1.215(6) . ?
O12 C35 1.326(6) . ?
O12 C36 1.454(5) . ?
N9 C26 1.379(6) . ?
N9 C27 1.379(6) . ?
N10 C27 1.331(6) . ?
N10 C28 1.431(6) . ?
N11 C34 1.328(6) . ?
N11 C33 1.419(6) . ?
N12 C35 1.376(6) . ?
N12 C34 1.380(6) . ?
C28 C29 1.375(7) . ?
C28 C33 1.385(7) . ?
C29 C30 1.388(7) . ?
C30 C31 1.383(8) . ?
C31 C32 1.380(7) . ?
C32 C33 1.398(6) . ?
N100 C100 1.133(8) . ?
C100 C101 1.429(9) . ?
N200 C200 1.125(11) . ?
C200 C201 1.435(13) . ?
N300 C300 1.031(19) . ?
C300 C301 1.52(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 115.7(4) . . ?
C11 O4 C12 116.0(9) . . ?
C2 N1 C3 126.7(4) . . ?
C3 N2 C4 122.5(4) . . ?
C10 N3 C9 122.4(5) . . ?
C11 N4 C10 128.1(7) . . ?
O1 C2 O2 125.3(5) . . ?
O1 C2 N1 125.4(5) . . ?
O2 C2 N1 109.2(4) . . ?
N2 C3 N1 117.2(4) . . ?
N2 C3 S1 123.8(4) . . ?
N1 C3 S1 119.0(4) . . ?
C9 C4 C5 120.3(4) . . ?
C9 C4 N2 120.4(5) . . ?
C5 C4 N2 119.3(4) . . ?
C4 C5 C6 119.9(5) . . ?
C7 C6 C5 119.9(5) . . ?
C6 C7 C8 120.4(5) . . ?
C7 C8 C9 119.7(5) . . ?
C4 C9 C8 119.8(5) . . ?
C4 C9 N3 121.1(4) . . ?
C8 C9 N3 119.1(5) . . ?
N4 C10 N3 114.7(7) . . ?
N4 C10 S2 120.3(6) . . ?
N3 C10 S2 125.0(5) . . ?
O3 C11 N4 128.0(8) . . ?
O3 C11 O4 121.3(10) . . ?
N4 C11 O4 110.6(9) . . ?
C14 O6 C13 115.3(4) . . ?
C23 O8 C24 115.5(4) . . ?
C14 N5 C15 128.2(4) . . ?
C15 N6 C16 126.3(4) . . ?
C22 N7 C21 123.1(4) . . ?
C23 N8 C22 127.3(4) . . ?
O5 C14 O6 125.7(4) . . ?
O5 C14 N5 125.7(5) . . ?
O6 C14 N5 108.6(4) . . ?
N6 C15 N5 116.2(4) . . ?
N6 C15 S3 125.6(4) . . ?
N5 C15 S3 118.2(3) . . ?
C21 C16 C17 118.9(5) . . ?
C21 C16 N6 117.5(4) . . ?
C17 C16 N6 123.5(5) . . ?
C18 C17 C16 119.3(5) . . ?
C19 C18 C17 121.2(5) . . ?
C20 C19 C18 120.2(5) . . ?
C19 C20 C21 119.1(5) . . ?
C20 C21 C16 121.3(4) . . ?
C20 C21 N7 120.6(5) . . ?
C16 C21 N7 118.1(4) . . ?
N7 C22 N8 116.1(4) . . ?
N7 C22 S4 124.6(4) . . ?
N8 C22 S4 119.3(3) . . ?
O7 C23 O8 125.3(5) . . ?
O7 C23 N8 126.2(4) . . ?
O8 C23 N8 108.5(4) . . ?
C26 O10 C25 115.8(4) . . ?
C35 O12 C36 115.3(4) . . ?
C26 N9 C27 127.1(4) . . ?
C27 N10 C28 122.5(4) . . ?
C34 N11 C33 127.7(4) . . ?
C35 N12 C34 127.3(4) . . ?
O9 C26 O10 126.0(4) . . ?
O9 C26 N9 125.3(4) . . ?
O10 C26 N9 108.6(4) . . ?
N10 C27 N9 117.7(4) . . ?
N10 C27 S5 122.7(4) . . ?
N9 C27 S5 119.6(3) . . ?
C29 C28 C33 120.4(4) . . ?
C29 C28 N10 120.3(4) . . ?
C33 C28 N10 119.3(4) . . ?
C28 C29 C30 119.9(5) . . ?
C31 C30 C29 120.1(5) . . ?
C32 C31 C30 120.2(5) . . ?
C31 C32 C33 119.6(5) . . ?
C28 C33 C32 119.8(4) . . ?
C28 C33 N11 118.1(4) . . ?
C32 C33 N11 122.1(4) . . ?
N11 C34 N12 115.6(4) . . ?
N11 C34 S6 125.7(4) . . ?
N12 C34 S6 118.7(3) . . ?
O11 C35 O12 125.3(4) . . ?
O11 C35 N12 125.8(5) . . ?
O12 C35 N12 108.8(4) . . ?
N100 C100 C101 179.4(8) . . ?
N200 C200 C201 178.3(12) . . ?
N300 C300 C301 173(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 -1.4(8) . . . . ?
C1 O2 C2 N1 179.0(5) . . . . ?
C3 N1 C2 O1 -4.0(9) . . . . ?
C3 N1 C2 O2 175.6(5) . . . . ?
C4 N2 C3 N1 -179.5(4) . . . . ?
C4 N2 C3 S1 -0.9(7) . . . . ?
C2 N1 C3 N2 3.8(8) . . . . ?
C2 N1 C3 S1 -174.9(4) . . . . ?
C3 N2 C4 C9 78.5(6) . . . . ?
C3 N2 C4 C5 -102.4(6) . . . . ?
C9 C4 C5 C6 0.1(8) . . . . ?
N2 C4 C5 C6 -178.9(5) . . . . ?
C4 C5 C6 C7 -0.6(8) . . . . ?
C5 C6 C7 C8 0.0(8) . . . . ?
C6 C7 C8 C9 1.1(8) . . . . ?
C5 C4 C9 C8 0.9(7) . . . . ?
N2 C4 C9 C8 179.9(4) . . . . ?
C5 C4 C9 N3 177.8(5) . . . . ?
N2 C4 C9 N3 -3.2(7) . . . . ?
C7 C8 C9 C4 -1.5(8) . . . . ?
C7 C8 C9 N3 -178.4(5) . . . . ?
C10 N3 C9 C4 76.6(7) . . . . ?
C10 N3 C9 C8 -106.5(6) . . . . ?
C11 N4 C10 N3 9.4(10) . . . . ?
C11 N4 C10 S2 -172.4(7) . . . . ?
C9 N3 C10 N4 -178.7(5) . . . . ?
C9 N3 C10 S2 3.2(8) . . . . ?
C10 N4 C11 O3 -9.1(15) . . . . ?
C10 N4 C11 O4 173.5(7) . . . . ?
C12 O4 C11 O3 0.7(12) . . . . ?
C12 O4 C11 N4 178.3(7) . . . . ?
C13 O6 C14 O5 -2.7(8) . . . . ?
C13 O6 C14 N5 176.8(4) . . . . ?
C15 N5 C14 O5 6.4(9) . . . . ?
C15 N5 C14 O6 -173.0(5) . . . . ?
C16 N6 C15 N5 170.0(5) . . . . ?
C16 N6 C15 S3 -9.6(8) . . . . ?
C14 N5 C15 N6 -12.1(8) . . . . ?
C14 N5 C15 S3 167.5(4) . . . . ?
C15 N6 C16 C21 -125.9(5) . . . . ?
C15 N6 C16 C17 56.3(7) . . . . ?
C21 C16 C17 C18 1.4(7) . . . . ?
N6 C16 C17 C18 179.2(5) . . . . ?
C16 C17 C18 C19 -0.5(8) . . . . ?
C17 C18 C19 C20 -0.6(9) . . . . ?
C18 C19 C20 C21 0.6(8) . . . . ?
C19 C20 C21 C16 0.4(8) . . . . ?
C19 C20 C21 N7 178.8(5) . . . . ?
C17 C16 C21 C20 -1.4(7) . . . . ?
N6 C16 C21 C20 -179.3(5) . . . . ?
C17 C16 C21 N7 -179.9(4) . . . . ?
N6 C16 C21 N7 2.2(7) . . . . ?
C22 N7 C21 C20 72.8(7) . . . . ?
C22 N7 C21 C16 -108.7(5) . . . . ?
C21 N7 C22 N8 172.8(4) . . . . ?
C21 N7 C22 S4 -7.3(7) . . . . ?
C23 N8 C22 N7 -8.7(7) . . . . ?
C23 N8 C22 S4 171.3(4) . . . . ?
C24 O8 C23 O7 -2.6(7) . . . . ?
C24 O8 C23 N8 177.1(4) . . . . ?
C22 N8 C23 O7 11.3(8) . . . . ?
C22 N8 C23 O8 -168.5(5) . . . . ?
C25 O10 C26 O9 -2.1(7) . . . . ?
C25 O10 C26 N9 -179.8(4) . . . . ?
C27 N9 C26 O9 -3.9(8) . . . . ?
C27 N9 C26 O10 173.8(5) . . . . ?
C28 N10 C27 N9 -177.6(4) . . . . ?
C28 N10 C27 S5 1.2(7) . . . . ?
C26 N9 C27 N10 6.8(7) . . . . ?
C26 N9 C27 S5 -171.9(4) . . . . ?
C27 N10 C28 C29 -92.9(6) . . . . ?
C27 N10 C28 C33 88.6(5) . . . . ?
C33 C28 C29 C30 1.9(7) . . . . ?
N10 C28 C29 C30 -176.6(4) . . . . ?
C28 C29 C30 C31 -1.1(8) . . . . ?
C29 C30 C31 C32 -0.4(8) . . . . ?
C30 C31 C32 C33 1.2(8) . . . . ?
C29 C28 C33 C32 -1.1(7) . . . . ?
N10 C28 C33 C32 177.4(4) . . . . ?
C29 C28 C33 N11 176.4(4) . . . . ?
N10 C28 C33 N11 -5.1(6) . . . . ?
C31 C32 C33 C28 -0.5(7) . . . . ?
C31 C32 C33 N11 -177.8(5) . . . . ?
C34 N11 C33 C28 137.2(5) . . . . ?
C34 N11 C33 C32 -45.4(7) . . . . ?
C33 N11 C34 N12 178.2(4) . . . . ?
C33 N11 C34 S6 -2.0(7) . . . . ?
C35 N12 C34 N11 4.8(7) . . . . ?
C35 N12 C34 S6 -175.1(4) . . . . ?
C36 O12 C35 O11 2.8(7) . . . . ?
C36 O12 C35 N12 -177.3(4) . . . . ?
C34 N12 C35 O11 4.7(8) . . . . ?
C34 N12 C35 O12 -175.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N S3 0.90(2) 2.59(2) 3.464(4) 165(5) 1_455
N2 H2N O1 0.90(2) 1.96(4) 2.662(5) 133(4) .
N2 H2N O5 0.90(2) 2.53(4) 3.235(5) 136(4) .
N3 H3N O3 0.91(2) 2.04(5) 2.669(7) 125(5) .
N4 H4N O400 0.92(2) 1.94(2) 2.859(10) 175(7) 2_666
N5 H5N S1 0.90(2) 2.45(3) 3.294(4) 156(5) 1_655
N6 H6N O5 0.90(2) 2.03(4) 2.722(5) 133(4) .
N6 H6N O1 0.90(2) 2.46(4) 3.163(6) 136(4) .
N7 H7N O7 0.90(2) 1.95(4) 2.690(5) 139(5) .
N7 H7N O9 0.90(2) 2.36(4) 3.034(5) 131(4) 1_565
N8 H8N S5 0.90(2) 2.41(2) 3.283(4) 166(4) 1_465
N9 H9N S4 0.90(2) 2.44(2) 3.334(4) 172(5) 1_645
N10 H10N O9 0.904(19) 2.01(4) 2.695(5) 132(4) .
N10 H10N O7 0.904(19) 2.31(4) 3.050(5) 139(4) 1_545
N11 H11N O11 0.92(2) 1.91(4) 2.665(5) 138(5) .
N12 H12N S6 0.90(2) 2.38(2) 3.268(4) 170(5) 2_665

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        66.81
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.084

data_TM_DCM
_database_code_depnum_ccdc_archive 'CCDC 724463'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, dichloromethane'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C1 H2 Cl2'
_chemical_formula_sum            'C13 H16 Cl2 N4 O4 S2'
_chemical_formula_weight         427.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   9.313(6)
_cell_length_b                   10.145(6)
_cell_length_c                   10.777(7)
_cell_angle_alpha                83.04(4)
_cell_angle_beta                 80.00(4)
_cell_angle_gamma                80.12(4)
_cell_volume                     983.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    5.187
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5938
_exptl_absorpt_correction_T_max  0.5938
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3274
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.18
_diffrn_reflns_theta_max         57.81
_reflns_number_total             1992
_reflns_number_gt                1492
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.1174P)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     SHELXL
_refine_ls_extinction_coef       0.041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1992
_refine_ls_number_parameters     238
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1881
_refine_ls_wR_factor_gt          0.1772
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.41480(15) 0.63430(13) 0.16266(12) 0.0547(6) Uani 1 1 d . . .
S2 S 0.33854(18) 0.16258(13) 0.56437(15) 0.0734(7) Uani 1 1 d . . .
O1 O 0.2176(4) 0.3752(4) -0.0891(3) 0.0631(11) Uani 1 1 d . . .
O2 O 0.0797(4) 0.3763(3) 0.1040(3) 0.0583(11) Uani 1 1 d . . .
O3 O 0.6027(4) 0.3156(3) 0.1940(3) 0.0573(10) Uani 1 1 d . . .
O4 O 0.7236(4) 0.1040(3) 0.2102(3) 0.0606(11) Uani 1 1 d . . .
N1 N 0.2718(5) 0.4976(4) 0.0454(4) 0.0496(11) Uani 1 1 d D . .
H1 H 0.338(4) 0.522(5) -0.018(3) 0.060 Uiso 1 1 d D . .
N2 N 0.1859(4) 0.5095(4) 0.2582(4) 0.0422(11) Uani 1 1 d D . .
H2 H 0.124(4) 0.457(4) 0.244(4) 0.051 Uiso 1 1 d D . .
N3 N 0.4018(4) 0.3700(4) 0.3970(4) 0.0421(10) Uani 1 1 d D . .
H3 H 0.4572 0.3989 0.3277 0.051 Uiso 1 1 calc RD . .
N4 N 0.5487(5) 0.1670(4) 0.3653(4) 0.0470(11) Uani 1 1 d D . .
H4 H 0.574(5) 0.081(2) 0.391(4) 0.056 Uiso 1 1 d D . .
C1 C 0.1375(7) 0.2772(6) -0.1204(6) 0.0741(18) Uani 1 1 d . . .
H1A H 0.1519 0.1953 -0.0628 0.111 Uiso 1 1 calc R . .
H1B H 0.1739 0.2561 -0.2077 0.111 Uiso 1 1 calc R . .
H1C H 0.0321 0.3138 -0.1119 0.111 Uiso 1 1 calc R . .
C2 C 0.1797(6) 0.4108(5) 0.0273(5) 0.0462(13) Uani 1 1 d . . .
C3 C 0.2820(6) 0.5435(4) 0.1584(5) 0.0443(13) Uani 1 1 d . . .
C4 C 0.1875(5) 0.5408(4) 0.3845(4) 0.0382(12) Uani 1 1 d . . .
C5 C 0.0820(5) 0.6403(5) 0.4366(5) 0.0493(13) Uani 1 1 d . . .
H5 H 0.0132 0.6915 0.3872 0.059 Uiso 1 1 calc R . .
C6 C 0.0765(6) 0.6653(5) 0.5597(5) 0.0530(15) Uani 1 1 d . . .
H6 H 0.0038 0.7337 0.5955 0.064 Uiso 1 1 calc R . .
C7 C 0.1756(7) 0.5916(5) 0.6307(5) 0.0539(15) Uani 1 1 d . . .
H7 H 0.1696 0.6079 0.7165 0.065 Uiso 1 1 calc R . .
C8 C 0.2856(6) 0.4926(5) 0.5791(5) 0.0489(13) Uani 1 1 d . . .
H8 H 0.3568 0.4442 0.6277 0.059 Uiso 1 1 calc R . .
C9 C 0.2886(5) 0.4667(4) 0.4556(4) 0.0389(12) Uani 1 1 d . . .
C10 C 0.4316(5) 0.2409(5) 0.4372(5) 0.0448(13) Uani 1 1 d . . .
C11 C 0.6237(6) 0.2054(5) 0.2505(5) 0.0454(13) Uani 1 1 d . . .
C12 C 0.8108(7) 0.1328(6) 0.0871(6) 0.082(2) Uani 1 1 d . . .
H12A H 0.7453 0.1588 0.0234 0.123 Uiso 1 1 calc R . .
H12B H 0.8808 0.0525 0.0642 0.123 Uiso 1 1 calc R . .
H12C H 0.8651 0.2065 0.0908 0.123 Uiso 1 1 calc R . .
Cl1 Cl 0.0748(4) 0.9870(3) 0.2854(4) 0.1747(13) Uani 1 1 d . . .
Cl2 Cl 0.3535(4) 1.0561(4) 0.1556(4) 0.1960(15) Uani 1 1 d . . .
C13 C 0.2614(12) 0.9650(9) 0.2935(10) 0.147(4) Uani 1 1 d . . .
H13A H 0.3027 0.8682 0.2957 0.176 Uiso 1 1 calc R . .
H13B H 0.2770 0.9991 0.3716 0.176 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
S1 C3 1.674(5) . ?
S2 C10 1.679(5) . ?
O1 C2 1.319(6) . ?
O1 C1 1.443(6) . ?
O2 C2 1.203(6) . ?
O3 C11 1.208(6) . ?
O4 C11 1.323(6) . ?
O4 C12 1.456(7) . ?
N1 C3 1.379(6) . ?
N1 C2 1.382(6) . ?
N1 H1 0.88(2) . ?
N2 C3 1.326(6) . ?
N2 C4 1.437(6) . ?
N2 H2 0.89(2) . ?
N3 C10 1.327(6) . ?
N3 C9 1.427(6) . ?
N3 H3 0.8800 . ?
N4 C11 1.359(7) . ?
N4 C10 1.385(6) . ?
N4 H4 0.89(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C9 1.380(7) . ?
C4 C5 1.381(6) . ?
C5 C6 1.371(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(7) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Cl1 C13 1.730(11) . ?
Cl2 C13 1.815(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 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
C2 O1 C1 115.3(4) . . ?
C11 O4 C12 114.8(4) . . ?
C3 N1 C2 126.7(4) . . ?
C3 N1 H1 114(3) . . ?
C2 N1 H1 119(3) . . ?
C3 N2 C4 124.0(4) . . ?
C3 N2 H2 115(3) . . ?
C4 N2 H2 120(3) . . ?
C10 N3 C9 126.2(4) . . ?
C10 N3 H3 116.9 . . ?
C9 N3 H3 116.9 . . ?
C11 N4 C10 128.0(4) . . ?
C11 N4 H4 113(3) . . ?
C10 N4 H4 118(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 126.0(5) . . ?
O2 C2 N1 125.5(5) . . ?
O1 C2 N1 108.4(5) . . ?
N2 C3 N1 116.9(4) . . ?
N2 C3 S1 124.2(4) . . ?
N1 C3 S1 118.9(4) . . ?
C9 C4 C5 120.3(4) . . ?
C9 C4 N2 120.2(4) . . ?
C5 C4 N2 119.4(4) . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.1(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 118.5(5) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C4 C9 C8 120.2(4) . . ?
C4 C9 N3 119.0(4) . . ?
C8 C9 N3 120.7(5) . . ?
N3 C10 N4 115.7(4) . . ?
N3 C10 S2 125.4(4) . . ?
N4 C10 S2 118.9(4) . . ?
O3 C11 O4 125.2(5) . . ?
O3 C11 N4 125.1(5) . . ?
O4 C11 N4 109.7(4) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Cl1 C13 Cl2 108.8(5) . . ?
Cl1 C13 H13A 109.9 . . ?
Cl2 C13 H13A 109.9 . . ?
Cl1 C13 H13B 109.9 . . ?
Cl2 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 O2 -5.5(7) . . . . ?
C1 O1 C2 N1 176.1(4) . . . . ?
C3 N1 C2 O2 10.9(8) . . . . ?
C3 N1 C2 O1 -170.7(4) . . . . ?
C4 N2 C3 N1 175.5(4) . . . . ?
C4 N2 C3 S1 -3.1(6) . . . . ?
C2 N1 C3 N2 -5.7(7) . . . . ?
C2 N1 C3 S1 173.0(4) . . . . ?
C3 N2 C4 C9 -77.3(5) . . . . ?
C3 N2 C4 C5 106.4(5) . . . . ?
C9 C4 C5 C6 -0.5(7) . . . . ?
N2 C4 C5 C6 175.8(4) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
C5 C6 C7 C8 1.6(7) . . . . ?
C6 C7 C8 C9 -2.6(7) . . . . ?
C5 C4 C9 C8 -0.7(6) . . . . ?
N2 C4 C9 C8 -176.9(4) . . . . ?
C5 C4 C9 N3 -176.3(4) . . . . ?
N2 C4 C9 N3 7.5(6) . . . . ?
C7 C8 C9 C4 2.2(6) . . . . ?
C7 C8 C9 N3 177.7(4) . . . . ?
C10 N3 C9 C4 -125.6(5) . . . . ?
C10 N3 C9 C8 58.9(6) . . . . ?
C9 N3 C10 N4 -179.1(4) . . . . ?
C9 N3 C10 S2 1.7(7) . . . . ?
C11 N4 C10 N3 -9.6(7) . . . . ?
C11 N4 C10 S2 169.6(4) . . . . ?
C12 O4 C11 O3 -0.6(8) . . . . ?
C12 O4 C11 N4 179.6(4) . . . . ?
C10 N4 C11 O3 3.2(8) . . . . ?
C10 N4 C11 O4 -177.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.89(2) 1.94(4) 2.673(5) 139(4) .
N3 H3 O3 0.88 1.96 2.666(5) 136.0 .
N3 H3 S1 0.88 2.81 3.456(4) 131.1 .
N1 H1 O3 0.88(2) 2.41(3) 3.185(5) 147(4) 2_665
N1 H1 S1 0.88(2) 2.89(4) 3.528(5) 131(4) 2_665
N4 H4 S2 0.89(2) 2.48(2) 3.364(4) 173(4) 2_656

_diffrn_measured_fraction_theta_max 0.731
_diffrn_reflns_theta_full        57.81
_diffrn_measured_fraction_theta_full 0.731
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.078

data_TM_12DCE
_database_code_depnum_ccdc_archive 'CCDC 724464'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, 1,2-dichloromethane'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C2 H4 Cl2'
_chemical_formula_sum            'C14 H18 Cl2 N4 O4 S2'
_chemical_formula_weight         441.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   9.313(2)
_cell_length_b                   10.150(2)
_cell_length_c                   10.735(2)
_cell_angle_alpha                82.061(11)
_cell_angle_beta                 79.396(12)
_cell_angle_gamma                79.411(12)
_cell_volume                     974.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    5.252
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.1090
_exptl_absorpt_correction_T_max  0.1591
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8006
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         57.70
_reflns_number_total             2410
_reflns_number_gt                2044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0579P)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     SHELXL
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2410
_refine_ls_number_parameters     250
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.08259(7) -0.12466(6) 0.84055(6) 0.0176(2) Uani 1 1 d . . .
S2 S 0.16496(7) 0.33701(7) 0.43363(6) 0.0208(2) Uani 1 1 d . . .
Cl1 Cl 0.41381(9) 0.51555(8) 0.73573(9) 0.0507(3) Uani 1 1 d . . .
Cl2 Cl 0.11967(9) 0.36729(7) 0.88046(8) 0.0410(3) Uani 1 1 d . . .
O1 O 0.4310(2) 0.11626(17) 0.89789(16) 0.0182(5) Uani 1 1 d . . .
O2 O 0.28678(19) 0.12666(17) 1.09217(16) 0.0178(5) Uani 1 1 d . . .
O3 O -0.11654(19) 0.17730(18) 0.79975(16) 0.0179(5) Uani 1 1 d . . .
O4 O -0.22628(19) 0.39575(17) 0.79018(16) 0.0193(5) Uani 1 1 d . . .
N1 N 0.2305(2) 0.0059(2) 0.9575(2) 0.0151(6) Uani 1 1 d D . .
H1 H 0.156(2) -0.011(2) 1.021(2) 0.018 Uiso 1 1 d D . .
N2 N 0.3188(2) -0.0085(2) 0.74223(19) 0.0138(5) Uani 1 1 d D . .
H2 H 0.385(2) 0.039(2) 0.758(2) 0.017 Uiso 1 1 d D . .
N3 N 0.0995(2) 0.1276(2) 0.6028(2) 0.0138(5) Uani 1 1 d D . .
H3 H 0.046(3) 0.098(2) 0.6758(18) 0.017 Uiso 1 1 d D . .
N4 N -0.0507(2) 0.3331(2) 0.6307(2) 0.0153(5) Uani 1 1 d D . .
H4 H -0.072(3) 0.4198(18) 0.607(2) 0.018 Uiso 1 1 d D . .
C1 C 0.3718(3) 0.2217(3) 1.1199(3) 0.0236(7) Uani 1 1 d . . .
H1A H 0.4765 0.1808 1.1120 0.035 Uiso 1 1 calc R . .
H1B H 0.3358 0.2455 1.2069 0.035 Uiso 1 1 calc R . .
H1C H 0.3607 0.3032 1.0594 0.035 Uiso 1 1 calc R . .
C2 C 0.3262(3) 0.0863(3) 0.9756(3) 0.0154(7) Uani 1 1 d . . .
C3 C 0.2186(3) -0.0391(2) 0.8443(2) 0.0153(7) Uani 1 1 d . . .
C4 C 0.3175(3) -0.0418(3) 0.6173(2) 0.0142(6) Uani 1 1 d . . .
C5 C 0.4250(3) -0.1427(3) 0.5660(2) 0.0160(7) Uani 1 1 d . . .
H5 H 0.4944 -0.1936 0.6161 0.019 Uiso 1 1 calc R . .
C6 C 0.4312(3) -0.1688(3) 0.4429(3) 0.0176(7) Uani 1 1 d . . .
H6 H 0.5048 -0.2377 0.4079 0.021 Uiso 1 1 calc R . .
C7 C 0.3299(3) -0.0947(3) 0.3694(3) 0.0178(7) Uani 1 1 d . . .
H7 H 0.3356 -0.1120 0.2837 0.021 Uiso 1 1 calc R . .
C8 C 0.2205(3) 0.0043(3) 0.4204(2) 0.0159(7) Uani 1 1 d . . .
H8 H 0.1498 0.0533 0.3706 0.019 Uiso 1 1 calc R . .
C9 C 0.2147(3) 0.0314(2) 0.5437(2) 0.0134(6) Uani 1 1 d . . .
C10 C 0.0687(3) 0.2583(3) 0.5610(2) 0.0165(7) Uani 1 1 d . . .
C11 C -0.1301(3) 0.2906(3) 0.7460(2) 0.0161(7) Uani 1 1 d . . .
C12 C -0.3164(3) 0.3620(3) 0.9128(2) 0.0241(7) Uani 1 1 d . . .
H12A H -0.3807 0.2991 0.9028 0.036 Uiso 1 1 calc R . .
H12B H -0.3774 0.4443 0.9433 0.036 Uiso 1 1 calc R . .
H12C H -0.2518 0.3200 0.9746 0.036 Uiso 1 1 calc R . .
C13 C 0.1136(4) 0.5368(3) 0.8065(3) 0.0331(8) Uani 1 1 d . . .
H13A H 0.0158 0.5683 0.7796 0.040 Uiso 1 1 calc R . .
H13B H 0.1236 0.5951 0.8700 0.040 Uiso 1 1 calc R . .
C14 C 0.2316(3) 0.5523(3) 0.6934(3) 0.0375(9) Uani 1 1 d . . .
H14A H 0.2150 0.6458 0.6517 0.045 Uiso 1 1 calc R . .
H14B H 0.2250 0.4910 0.6313 0.045 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
S1 C3 1.672(3) . ?
S2 C10 1.680(3) . ?
Cl1 C14 1.797(3) . ?
Cl2 C13 1.788(3) . ?
O1 C2 1.217(3) . ?
O2 C2 1.336(3) . ?
O2 C1 1.446(3) . ?
O3 C11 1.208(3) . ?
O4 C11 1.341(3) . ?
O4 C12 1.459(3) . ?
N1 C2 1.369(3) . ?
N1 C3 1.385(3) . ?
N2 C3 1.343(3) . ?
N2 C4 1.430(3) . ?
N3 C10 1.336(3) . ?
N3 C9 1.429(3) . ?
N4 C11 1.379(3) . ?
N4 C10 1.383(3) . ?
C4 C5 1.390(4) . ?
C4 C9 1.396(3) . ?
C5 C6 1.372(4) . ?
C6 C7 1.388(4) . ?
C7 C8 1.384(4) . ?
C8 C9 1.379(3) . ?
C13 C14 1.492(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
C2 O2 C1 115.0(2) . . ?
C11 O4 C12 113.59(19) . . ?
C2 N1 C3 127.4(2) . . ?
C3 N2 C4 123.5(2) . . ?
C10 N3 C9 125.8(2) . . ?
C11 N4 C10 126.6(2) . . ?
O1 C2 O2 125.3(2) . . ?
O1 C2 N1 125.4(3) . . ?
O2 C2 N1 109.3(2) . . ?
N2 C3 N1 116.6(2) . . ?
N2 C3 S1 123.8(2) . . ?
N1 C3 S1 119.5(2) . . ?
C5 C4 C9 119.7(2) . . ?
C5 C4 N2 119.6(2) . . ?
C9 C4 N2 120.5(2) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 C7 120.1(2) . . ?
C8 C7 C6 120.3(2) . . ?
C9 C8 C7 119.7(2) . . ?
C8 C9 C4 120.1(2) . . ?
C8 C9 N3 121.8(2) . . ?
C4 C9 N3 118.0(2) . . ?
N3 C10 N4 116.4(2) . . ?
N3 C10 S2 125.1(2) . . ?
N4 C10 S2 118.5(2) . . ?
O3 C11 O4 124.9(2) . . ?
O3 C11 N4 126.1(2) . . ?
O4 C11 N4 108.9(2) . . ?
C14 C13 Cl2 113.5(2) . . ?
C13 C14 Cl1 112.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 5.1(3) . . . . ?
C1 O2 C2 N1 -175.11(19) . . . . ?
C3 N1 C2 O1 -11.0(4) . . . . ?
C3 N1 C2 O2 169.2(2) . . . . ?
C4 N2 C3 N1 -176.9(2) . . . . ?
C4 N2 C3 S1 2.1(3) . . . . ?
C2 N1 C3 N2 5.0(4) . . . . ?
C2 N1 C3 S1 -174.06(19) . . . . ?
C3 N2 C4 C5 -108.4(3) . . . . ?
C3 N2 C4 C9 75.4(3) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
N2 C4 C5 C6 -175.4(2) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 1.6(4) . . . . ?
C7 C8 C9 C4 -0.8(4) . . . . ?
C7 C8 C9 N3 -176.7(2) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
N2 C4 C9 C8 175.8(2) . . . . ?
C5 C4 C9 N3 175.6(2) . . . . ?
N2 C4 C9 N3 -8.2(3) . . . . ?
C10 N3 C9 C8 -59.4(4) . . . . ?
C10 N3 C9 C4 124.7(3) . . . . ?
C9 N3 C10 N4 178.2(2) . . . . ?
C9 N3 C10 S2 -3.0(4) . . . . ?
C11 N4 C10 N3 7.8(4) . . . . ?
C11 N4 C10 S2 -171.1(2) . . . . ?
C12 O4 C11 O3 0.1(4) . . . . ?
C12 O4 C11 N4 -179.8(2) . . . . ?
C10 N4 C11 O3 -6.8(4) . . . . ?
C10 N4 C11 O4 173.2(2) . . . . ?
Cl2 C13 C14 Cl1 -65.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.902(16) 1.94(2) 2.684(3) 139(2) .
N3 H3 O3 0.895(16) 1.95(2) 2.670(3) 136(2) .
N3 H3 S1 0.895(16) 2.68(2) 3.360(2) 133(2) .
N1 H1 O3 0.901(17) 2.39(2) 3.121(3) 138(2) 2_557
N1 H1 S1 0.901(17) 2.70(2) 3.429(2) 139(2) 2_557
N4 H4 S2 0.878(17) 2.468(18) 3.338(2) 171(2) 2_566

_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_theta_full        57.70
_diffrn_measured_fraction_theta_full 0.897
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.065

data_TM_MeOH
_database_code_depnum_ccdc_archive 'CCDC 724465'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, methanol'
_chemical_melting_point          ?
_chemical_formula_moiety         '2 C12 H14 N4 O4 S2, C1 H4 O1'
_chemical_formula_sum            'C25 H32 N8 O9 S4'
_chemical_formula_weight         716.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.016(3)
_cell_length_b                   11.430(3)
_cell_length_c                   15.904(5)
_cell_angle_alpha                101.734(10)
_cell_angle_beta                 90.330(11)
_cell_angle_gamma                107.692(9)
_cell_volume                     1694.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7468
_exptl_absorpt_correction_T_max  0.8604
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7892
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         10.32
_diffrn_reflns_theta_max         54.79
_reflns_number_total             3543
_reflns_number_gt                2428
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
The disordered methanol could not be refined anisotropically and was thus left
as isotropic.
Positions for the hydrogen atoms on the methanol molecule could not be
accurately found and were left out of the model.
;

_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)+(0.1121P)²+3.1676P] 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     SHELXL
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3543
_refine_ls_number_parameters     443
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2339
_refine_ls_wR_factor_gt          0.1975
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.8544(2) 0.73682(19) 0.41812(14) 0.0674(7) Uani 1 1 d . . .
S2 S 1.0591(3) 0.4343(3) 0.11062(15) 0.1115(12) Uani 1 1 d . . .
S3 S 0.2280(2) 0.93911(17) 0.57554(13) 0.0629(7) Uani 1 1 d . . .
S4 S 0.4566(4) 0.7816(4) 0.87559(18) 0.1238(13) Uani 1 1 d . . .
O1 O 1.2171(6) 0.9472(5) 0.2814(4) 0.0670(15) Uani 1 1 d . . .
O2 O 1.1058(6) 1.0934(5) 0.3041(4) 0.0722(17) Uani 1 1 d . . .
O3 O 0.7248(8) 0.6230(7) 0.1856(5) 0.103(2) Uani 1 1 d . . .
O4 O 0.6939(7) 0.5977(7) 0.0432(4) 0.102(2) Uani 1 1 d . . .
O5 O 0.6196(5) 1.2376(4) 0.7183(4) 0.0653(15) Uani 1 1 d . . .
O6 O 0.5021(5) 1.3674(4) 0.6932(3) 0.0581(14) Uani 1 1 d . . .
O7 O 0.1792(9) 0.9974(8) 0.8003(6) 0.124(3) Uani 1 1 d . . .
O8 O 0.1525(8) 1.0362(7) 0.9393(5) 0.110(2) Uani 1 1 d . . .
N1 N 1.0182(7) 0.9208(6) 0.3532(4) 0.0541(17) Uani 1 1 d D . .
H1 H 0.958(7) 0.955(7) 0.383(5) 0.081 Uiso 1 1 d D . .
N2 N 1.0941(6) 0.7467(5) 0.3471(4) 0.0465(15) Uani 1 1 d D . .
H2 H 1.174(5) 0.774(7) 0.321(4) 0.070 Uiso 1 1 d D . .
N3 N 0.9239(7) 0.5343(6) 0.2332(4) 0.0540(16) Uani 1 1 d D . .
H3 H 0.859(7) 0.573(7) 0.246(5) 0.081 Uiso 1 1 d D . .
N4 N 0.8574(8) 0.5334(8) 0.0940(4) 0.079(2) Uani 1 1 d D . .
H4 H 0.884(11) 0.524(10) 0.039(3) 0.118 Uiso 1 1 d D . .
N5 N 0.4003(6) 1.1646(5) 0.6470(4) 0.0489(16) Uani 1 1 d D . .
H5 H 0.325(6) 1.189(7) 0.633(5) 0.073 Uiso 1 1 d D . .
N6 N 0.4850(6) 0.9972(5) 0.6496(4) 0.0503(16) Uani 1 1 d D . .
H6 H 0.557(6) 1.049(6) 0.688(4) 0.075 Uiso 1 1 d D . .
N7 N 0.3311(7) 0.8425(6) 0.7524(5) 0.0611(18) Uani 1 1 d D . .
H7 H 0.266(7) 0.877(8) 0.740(6) 0.092 Uiso 1 1 d D . .
N8 N 0.2790(9) 0.9118(8) 0.8903(5) 0.089(2) Uani 1 1 d D . .
H8 H 0.317(12) 0.936(10) 0.945(3) 0.133 Uiso 1 1 d D . .
C1 C 1.2016(10) 1.1648(8) 0.2501(6) 0.078(3) Uani 1 1 d . . .
H1A H 1.2977 1.1927 0.2766 0.117 Uiso 1 1 calc R . .
H1B H 1.1739 1.2383 0.2446 0.117 Uiso 1 1 calc R . .
H1C H 1.1973 1.1113 0.1929 0.117 Uiso 1 1 calc R . .
C2 C 1.1239(9) 0.9850(7) 0.3097(5) 0.052(2) Uani 1 1 d . . .
C3 C 0.9973(7) 0.8022(6) 0.3704(4) 0.0433(18) Uani 1 1 d . . .
C4 C 1.0834(7) 0.6237(6) 0.3613(4) 0.0446(18) Uani 1 1 d . . .
C5 C 1.1569(8) 0.6116(6) 0.4301(4) 0.0493(19) Uani 1 1 d . . .
H5A H 1.2138 0.6845 0.4692 0.059 Uiso 1 1 calc R . .
C6 C 1.1485(9) 0.4954(7) 0.4427(5) 0.062(2) Uani 1 1 d . . .
H6A H 1.2001 0.4877 0.4905 0.075 Uiso 1 1 calc R . .
C7 C 1.0659(9) 0.3891(7) 0.3869(6) 0.064(2) Uani 1 1 d . . .
H7A H 1.0584 0.3083 0.3970 0.076 Uiso 1 1 calc R . .
C8 C 0.9937(8) 0.4001(7) 0.3157(5) 0.059(2) Uani 1 1 d . . .
H8A H 0.9379 0.3268 0.2765 0.070 Uiso 1 1 calc R . .
C9 C 1.0031(7) 0.5184(6) 0.3017(4) 0.0463(18) Uani 1 1 d . . .
C10 C 0.9415(8) 0.5030(8) 0.1517(5) 0.064(2) Uani 1 1 d . . .
C11 C 0.7543(10) 0.5877(9) 0.1150(7) 0.076(3) Uani 1 1 d . . .
C12 C 0.5862(13) 0.6617(12) 0.0566(8) 0.122(4) Uani 1 1 d . . .
H12A H 0.4961 0.6012 0.0639 0.183 Uiso 1 1 calc R . .
H12B H 0.5765 0.6970 0.0065 0.183 Uiso 1 1 calc R . .
H12C H 0.6142 0.7295 0.1082 0.183 Uiso 1 1 calc R . .
C13 C 0.6113(9) 1.4730(7) 0.7442(6) 0.069(2) Uani 1 1 d . . .
H13A H 0.6601 1.4432 0.7849 0.103 Uiso 1 1 calc R . .
H13B H 0.5691 1.5340 0.7762 0.103 Uiso 1 1 calc R . .
H13C H 0.6786 1.5132 0.7062 0.103 Uiso 1 1 calc R . .
C14 C 0.5170(8) 1.2560(6) 0.6890(5) 0.0477(18) Uani 1 1 d . . .
C15 C 0.3779(7) 1.0350(6) 0.6266(4) 0.0481(19) Uani 1 1 d . . .
C16 C 0.4749(8) 0.8665(6) 0.6336(5) 0.050(2) Uani 1 1 d . . .
C17 C 0.5478(9) 0.8213(7) 0.5703(5) 0.066(2) Uani 1 1 d . . .
H17A H 0.6036 0.8762 0.5375 0.079 Uiso 1 1 calc R . .
C18 C 0.5420(10) 0.6946(8) 0.5527(6) 0.074(3) Uani 1 1 d . . .
H18A H 0.5908 0.6630 0.5070 0.089 Uiso 1 1 calc R . .
C19 C 0.4646(10) 0.6165(8) 0.6023(6) 0.071(2) Uani 1 1 d . . .
H19A H 0.4601 0.5304 0.5912 0.085 Uiso 1 1 calc R . .
C20 C 0.3933(9) 0.6636(7) 0.6688(6) 0.068(2) Uani 1 1 d . . .
H20A H 0.3394 0.6093 0.7026 0.081 Uiso 1 1 calc R . .
C21 C 0.4002(8) 0.7891(6) 0.6861(5) 0.052(2) Uani 1 1 d . . .
C22 C 0.3523(10) 0.8495(8) 0.8349(6) 0.075(2) Uani 1 1 d . . .
C23 C 0.2004(11) 0.9820(9) 0.8707(8) 0.086(3) Uani 1 1 d . . .
C24 C 0.0586(14) 1.1072(12) 0.9274(9) 0.130(5) Uani 1 1 d . . .
H24A H 0.0988 1.1641 0.8891 0.195 Uiso 1 1 calc R . .
H24B H 0.0464 1.1564 0.9833 0.195 Uiso 1 1 calc R . .
H24C H -0.0328 1.0492 0.9018 0.195 Uiso 1 1 calc R . .
O9A O 0.324(3) 0.950(3) 0.0606(13) 0.142(8) Uiso 0.52(3) 1 d P A 1
C25A C 0.336(3) 0.848(2) 0.0948(14) 0.101(10) Uiso 0.52(3) 1 d P A 1
O9B O 0.265(3) 0.888(2) 0.0685(11) 0.116(8) Uiso 0.48(3) 1 d P A 2
C25B C 0.243(3) 0.768(2) 0.0831(14) 0.096(10) Uiso 0.48(3) 1 d P A 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
S1 C3 1.666(7) . ?
S2 C10 1.671(8) . ?
S3 C15 1.654(7) . ?
S4 C22 1.674(9) . ?
O1 C2 1.197(9) . ?
O2 C2 1.325(9) . ?
O2 C1 1.464(10) . ?
O3 C11 1.184(10) . ?
O4 C11 1.330(10) . ?
O4 C12 1.471(11) . ?
O5 C14 1.218(8) . ?
O6 C14 1.316(8) . ?
O6 C13 1.450(9) . ?
O7 C23 1.197(12) . ?
O8 C23 1.309(12) . ?
O8 C24 1.451(12) . ?
N1 C2 1.371(10) . ?
N1 C3 1.391(9) . ?
N1 H1 0.90(2) . ?
N2 C3 1.328(8) . ?
N2 C4 1.441(8) . ?
N2 H2 0.90(2) . ?
N3 C10 1.300(9) . ?
N3 C9 1.417(9) . ?
N3 H3 0.90(2) . ?
N4 C11 1.368(11) . ?
N4 C10 1.404(10) . ?
N4 H4 0.92(2) . ?
N5 C14 1.367(9) . ?
N5 C15 1.397(8) . ?
N5 H5 0.92(2) . ?
N6 C15 1.347(8) . ?
N6 C16 1.434(8) . ?
N6 H6 0.91(2) . ?
N7 C22 1.310(10) . ?
N7 C21 1.403(10) . ?
N7 H7 0.90(2) . ?
N8 C23 1.358(13) . ?
N8 C22 1.376(11) . ?
N8 H8 0.90(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.369(9) . ?
C4 C9 1.391(9) . ?
C5 C6 1.361(9) . ?
C5 H5A 0.9500 . ?
C6 C7 1.376(10) . ?
C6 H6A 0.9500 . ?
C7 C8 1.387(11) . ?
C7 H7A 0.9500 . ?
C8 C9 1.390(10) . ?
C8 H8A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 C17 1.357(11) . ?
C16 C21 1.395(10) . ?
C17 C18 1.400(11) . ?
C17 H17A 0.9500 . ?
C18 C19 1.376(12) . ?
C18 H18A 0.9500 . ?
C19 C20 1.388(12) . ?
C19 H19A 0.9500 . ?
C20 C21 1.384(10) . ?
C20 H20A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O9A C25A 1.41(3) . ?
O9B C25B 1.39(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 115.3(6) . . ?
C11 O4 C12 114.9(8) . . ?
C14 O6 C13 115.9(6) . . ?
C23 O8 C24 118.0(9) . . ?
C2 N1 C3 127.4(6) . . ?
C2 N1 H1 124(6) . . ?
C3 N1 H1 108(6) . . ?
C3 N2 C4 122.2(6) . . ?
C3 N2 H2 130(5) . . ?
C4 N2 H2 108(5) . . ?
C10 N3 C9 125.7(6) . . ?
C10 N3 H3 116(5) . . ?
C9 N3 H3 118(5) . . ?
C11 N4 C10 126.2(7) . . ?
C11 N4 H4 119(7) . . ?
C10 N4 H4 115(7) . . ?
C14 N5 C15 127.2(6) . . ?
C14 N5 H5 118(5) . . ?
C15 N5 H5 115(5) . . ?
C15 N6 C16 121.4(6) . . ?
C15 N6 H6 122(5) . . ?
C16 N6 H6 115(5) . . ?
C22 N7 C21 126.3(7) . . ?
C22 N7 H7 114(6) . . ?
C21 N7 H7 120(6) . . ?
C23 N8 C22 127.2(9) . . ?
C23 N8 H8 114(7) . . ?
C22 N8 H8 113(8) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 126.1(8) . . ?
O1 C2 N1 124.3(7) . . ?
O2 C2 N1 109.6(7) . . ?
N2 C3 N1 117.2(6) . . ?
N2 C3 S1 123.4(5) . . ?
N1 C3 S1 119.4(5) . . ?
C5 C4 C9 120.9(6) . . ?
C5 C4 N2 120.2(6) . . ?
C9 C4 N2 118.8(6) . . ?
C6 C5 C4 120.1(6) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C7 120.5(7) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C8 119.8(7) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C7 C8 C9 120.0(7) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 C4 118.5(6) . . ?
C8 C9 N3 122.0(6) . . ?
C4 C9 N3 119.3(6) . . ?
N3 C10 N4 116.9(7) . . ?
N3 C10 S2 125.5(6) . . ?
N4 C10 S2 117.6(6) . . ?
O3 C11 O4 125.0(9) . . ?
O3 C11 N4 125.9(8) . . ?
O4 C11 N4 109.1(9) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 124.9(7) . . ?
O5 C14 N5 125.4(6) . . ?
O6 C14 N5 109.8(6) . . ?
N6 C15 N5 115.8(6) . . ?
N6 C15 S3 124.3(5) . . ?
N5 C15 S3 119.9(5) . . ?
C17 C16 C21 120.2(7) . . ?
C17 C16 N6 118.8(7) . . ?
C21 C16 N6 120.8(6) . . ?
C16 C17 C18 120.9(8) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C19 C18 C17 119.3(8) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C18 C19 C20 119.9(8) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C21 C20 C19 120.5(8) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C16 119.1(7) . . ?
C20 C21 N7 123.3(8) . . ?
C16 C21 N7 117.5(6) . . ?
N7 C22 N8 117.4(7) . . ?
N7 C22 S4 123.8(7) . . ?
N8 C22 S4 118.7(7) . . ?
O7 C23 O8 122.6(10) . . ?
O7 C23 N8 125.4(9) . . ?
O8 C23 N8 112.0(11) . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 7.0(11) . . . . ?
C1 O2 C2 N1 -172.9(7) . . . . ?
C3 N1 C2 O1 -1.7(12) . . . . ?
C3 N1 C2 O2 178.1(6) . . . . ?
C4 N2 C3 N1 -179.7(6) . . . . ?
C4 N2 C3 S1 0.0(9) . . . . ?
C2 N1 C3 N2 4.4(10) . . . . ?
C2 N1 C3 S1 -175.4(6) . . . . ?
C3 N2 C4 C5 -99.4(8) . . . . ?
C3 N2 C4 C9 83.7(8) . . . . ?
C9 C4 C5 C6 -2.2(11) . . . . ?
N2 C4 C5 C6 -178.9(6) . . . . ?
C4 C5 C6 C7 -0.3(12) . . . . ?
C5 C6 C7 C8 1.9(12) . . . . ?
C6 C7 C8 C9 -1.0(12) . . . . ?
C7 C8 C9 C4 -1.3(11) . . . . ?
C7 C8 C9 N3 -175.7(7) . . . . ?
C5 C4 C9 C8 3.0(10) . . . . ?
N2 C4 C9 C8 179.8(6) . . . . ?
C5 C4 C9 N3 177.4(7) . . . . ?
N2 C4 C9 N3 -5.7(10) . . . . ?
C10 N3 C9 C8 -68.4(11) . . . . ?
C10 N3 C9 C4 117.3(8) . . . . ?
C9 N3 C10 N4 -176.3(7) . . . . ?
C9 N3 C10 S2 1.5(12) . . . . ?
C11 N4 C10 N3 -3.2(14) . . . . ?
C11 N4 C10 S2 178.8(8) . . . . ?
C12 O4 C11 O3 2.0(15) . . . . ?
C12 O4 C11 N4 -176.5(9) . . . . ?
C10 N4 C11 O3 3.9(17) . . . . ?
C10 N4 C11 O4 -177.6(8) . . . . ?
C13 O6 C14 O5 -6.4(10) . . . . ?
C13 O6 C14 N5 173.5(6) . . . . ?
C15 N5 C14 O5 -2.9(12) . . . . ?
C15 N5 C14 O6 177.2(6) . . . . ?
C16 N6 C15 N5 179.0(6) . . . . ?
C16 N6 C15 S3 -2.1(10) . . . . ?
C14 N5 C15 N6 -1.3(10) . . . . ?
C14 N5 C15 S3 179.7(6) . . . . ?
C15 N6 C16 C17 106.9(8) . . . . ?
C15 N6 C16 C21 -77.9(9) . . . . ?
C21 C16 C17 C18 4.3(12) . . . . ?
N6 C16 C17 C18 179.5(7) . . . . ?
C16 C17 C18 C19 -2.1(12) . . . . ?
C17 C18 C19 C20 0.2(13) . . . . ?
C18 C19 C20 C21 -0.6(12) . . . . ?
C19 C20 C21 C16 2.7(11) . . . . ?
C19 C20 C21 N7 -179.8(8) . . . . ?
C17 C16 C21 C20 -4.6(11) . . . . ?
N6 C16 C21 C20 -179.7(6) . . . . ?
C17 C16 C21 N7 177.7(7) . . . . ?
N6 C16 C21 N7 2.6(10) . . . . ?
C22 N7 C21 C20 61.7(11) . . . . ?
C22 N7 C21 C16 -120.8(9) . . . . ?
C21 N7 C22 N8 176.5(8) . . . . ?
C21 N7 C22 S4 -6.5(13) . . . . ?
C23 N8 C22 N7 -9.6(16) . . . . ?
C23 N8 C22 S4 173.3(9) . . . . ?
C24 O8 C23 O7 6.4(17) . . . . ?
C24 O8 C23 N8 -175.8(9) . . . . ?
C22 N8 C23 O7 2.5(19) . . . . ?
C22 N8 C23 O8 -175.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.90(2) 2.12(7) 2.671(7) 119(6) .
N3 H3 O3 0.90(2) 1.93(6) 2.665(8) 138(7) .
N3 H3 S1 0.90(2) 2.99(7) 3.568(6) 124(6) .
N6 H6 O5 0.91(2) 2.01(6) 2.660(7) 128(6) .
N7 H7 O7 0.90(2) 1.94(6) 2.671(8) 137(8) .
N7 H7 S3 0.90(2) 2.90(8) 3.482(7) 124(7) .
N1 H1 S3 0.90(2) 2.54(3) 3.410(6) 164(7) 2_676
N2 H2 O5 0.90(2) 2.20(4) 3.022(8) 152(7) 2_776
N4 H4 S2 0.92(2) 2.55(4) 3.429(8) 162(9) 2_765
N5 H5 S1 0.92(2) 2.41(2) 3.323(6) 173(7) 2_676
N6 H6 O1 0.91(2) 2.30(6) 3.006(8) 134(6) 2_776
N8 H8 O9A 0.90(2) 1.81(5) 2.67(2) 158(12) 1_556
N8 H8 O9B 0.90(2) 2.17(9) 2.90(2) 138(10) 1_556

_diffrn_measured_fraction_theta_max 0.838
_diffrn_reflns_theta_full        54.79
_diffrn_measured_fraction_theta_full 0.838
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.079

data_TM_EtOH
_database_code_depnum_ccdc_archive 'CCDC 724466'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, ethanol'
_chemical_melting_point          ?
_chemical_formula_moiety         '2 C12 H14 N4 O4 S2, C2 H6 O1'
_chemical_formula_sum            'C26 H34 N8 O9 S4'
_chemical_formula_weight         730.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.8415(19)
_cell_length_b                   11.370(2)
_cell_length_c                   15.988(3)
_cell_angle_alpha                78.986(10)
_cell_angle_beta                 89.335(10)
_cell_angle_gamma                72.146(11)
_cell_volume                     1669.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             764
_exptl_absorpt_coefficient_mu    3.158
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7430
_exptl_absorpt_correction_T_max  0.8581
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9780
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         57.52
_reflns_number_total             3869
_reflns_number_gt                3032
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.2000P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3869
_refine_ls_number_parameters     400
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1835
_refine_ls_R_factor_gt           0.1717
_refine_ls_wR_factor_ref         0.4969
_refine_ls_wR_factor_gt          0.4942
_refine_ls_goodness_of_fit_ref   2.166
_refine_ls_restrained_S_all      2.168
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.2222(4) 0.5647(4) 0.0711(2) 0.0228(13) Uani 1 1 d . . .
S2 S 0.4317(4) 0.7357(4) 0.3713(2) 0.0259(13) Uani 1 1 d . . .
S3 S -0.0588(4) -0.0777(4) 0.3906(3) 0.0292(14) Uani 1 1 d . . .
S4 S 0.1418(4) 0.2394(4) 0.0781(3) 0.0279(14) Uani 1 1 d . . .
O1 O 0.6110(10) 0.2660(9) 0.2177(6) 0.025(3) Uani 1 1 d . . .
O2 O 0.4956(9) 0.1341(9) 0.1907(6) 0.020(3) Uani 1 1 d . . .
O3 O 0.1575(12) 0.5085(11) 0.2930(7) 0.037(3) Uani 1 1 d . . .
O4 O 0.1404(11) 0.4615(10) 0.4342(6) 0.029(3) Uani 1 1 d . . .
O5 O 0.2699(11) 0.1291(11) 0.3126(7) 0.036(3) Uani 1 1 d . . .
O6 O 0.3054(11) 0.0974(10) 0.4551(7) 0.030(3) Uani 1 1 d . . .
O7 O -0.2283(11) 0.4526(9) 0.2202(7) 0.023(3) Uani 1 1 d . . .
O8 O -0.1162(10) 0.6013(9) 0.1938(7) 0.022(3) Uani 1 1 d . . .
N1 N 0.3934(12) 0.3401(11) 0.1433(7) 0.018(3) Uani 1 1 d D . .
H1 H 0.3239 0.3155 0.1260 0.022 Uiso 1 1 calc RD . .
N2 N 0.4807(13) 0.5080(11) 0.1467(7) 0.019(3) Uani 1 1 d D . .
H2 H 0.5583 0.4519 0.1731 0.023 Uiso 1 1 calc RD . .
N3 N 0.3149(12) 0.6655(11) 0.2479(8) 0.017(3) Uani 1 1 d D . .
H3 H 0.2507 0.6325 0.2335 0.021 Uiso 1 1 calc RD . .
N4 N 0.2622(12) 0.5918(11) 0.3853(8) 0.020(2) Uani 1 1 d D . .
H4 H 0.2704 0.5929 0.4399 0.024 Uiso 1 1 calc RD . .
N5 N 0.1377(12) 0.0324(12) 0.4049(8) 0.024(3) Uani 1 1 d D . .
H5 H 0.1238 0.0137 0.4596 0.029 Uiso 1 1 calc RD . .
N6 N 0.0679(12) 0.0383(11) 0.2657(8) 0.022(3) Uani 1 1 d D . .
H6 H 0.1318 0.0776 0.2519 0.026 Uiso 1 1 calc RD . .
N7 N -0.1017(12) 0.2498(11) 0.1527(8) 0.018(3) Uani 1 1 d D . .
H7 H -0.1779 0.2896 0.1772 0.022 Uiso 1 1 calc RD . .
N8 N -0.0234(13) 0.4265(11) 0.1446(8) 0.021(3) Uani 1 1 d D . .
H8 H 0.0385 0.4649 0.1240 0.025 Uiso 1 1 calc RD . .
C1 C 0.6012(16) 0.0289(13) 0.2416(10) 0.021(4) Uani 1 1 d . . .
H1A H 0.6861 0.0029 0.2086 0.031 Uiso 1 1 calc R . .
H1B H 0.5621 -0.0413 0.2578 0.031 Uiso 1 1 calc R . .
H1C H 0.6276 0.0534 0.2931 0.031 Uiso 1 1 calc R . .
C2 C 0.5092(16) 0.2464(14) 0.1874(9) 0.018(3) Uani 1 1 d . . .
C3 C 0.3749(16) 0.4679(15) 0.1234(9) 0.023(4) Uani 1 1 d . . .
C4 C 0.4730(15) 0.6383(14) 0.1303(10) 0.018(4) Uani 1 1 d . . .
C5 C 0.5498(15) 0.6819(15) 0.0696(9) 0.017(4) Uani 1 1 d . . .
H5A H 0.6065 0.6262 0.0362 0.021 Uiso 1 1 calc R . .
C6 C 0.5489(15) 0.8087(16) 0.0539(10) 0.026(4) Uani 1 1 d . . .
H6A H 0.6057 0.8389 0.0119 0.031 Uiso 1 1 calc R . .
C7 C 0.4624(16) 0.8856(15) 0.1018(10) 0.026(3) Uani 1 1 d . . .
H7A H 0.4556 0.9724 0.0904 0.032 Uiso 1 1 calc R . .
C8 C 0.3832(16) 0.8418(14) 0.1673(10) 0.026(3) Uani 1 1 d . . .
H8A H 0.3286 0.8967 0.2019 0.032 Uiso 1 1 calc R . .
C9 C 0.3863(16) 0.7146(14) 0.1807(10) 0.023(4) Uani 1 1 d . . .
C10 C 0.3314(14) 0.6623(14) 0.3300(10) 0.020(2) Uani 1 1 d . . .
C11 C 0.1825(15) 0.5208(14) 0.3641(10) 0.018(3) Uani 1 1 d . . .
C12 C 0.0485(19) 0.3893(17) 0.4204(13) 0.042(5) Uani 1 1 d . . .
H12A H -0.0455 0.4466 0.3977 0.063 Uiso 1 1 calc R . .
H12B H 0.0379 0.3364 0.4746 0.063 Uiso 1 1 calc R . .
H12C H 0.0905 0.3357 0.3796 0.063 Uiso 1 1 calc R . .
C13 C 0.4114(18) 0.1603(18) 0.4452(12) 0.037(5) Uani 1 1 d . . .
H13A H 0.4952 0.1098 0.4201 0.055 Uiso 1 1 calc R . .
H13B H 0.4395 0.1713 0.5011 0.055 Uiso 1 1 calc R . .
H13C H 0.3724 0.2430 0.4076 0.055 Uiso 1 1 calc R . .
C14 C 0.2402(15) 0.0906(16) 0.3840(11) 0.025(4) Uani 1 1 d . . .
C15 C 0.0530(16) -0.0006(14) 0.3500(11) 0.026(4) Uani 1 1 d . . .
C16 C -0.0106(15) 0.0208(14) 0.1981(9) 0.018(3) Uani 1 1 d . . .
C17 C -0.0017(15) -0.0995(15) 0.1835(9) 0.021(4) Uani 1 1 d . . .
H17 H 0.0527 -0.1725 0.2226 0.025 Uiso 1 1 calc R . .
C18 C -0.0723(15) -0.1128(14) 0.1120(10) 0.023(3) Uani 1 1 d . . .
H18 H -0.0652 -0.1940 0.1017 0.028 Uiso 1 1 calc R . .
C19 C -0.1528(15) -0.0050(14) 0.0565(10) 0.023(3) Uani 1 1 d . . .
H19 H -0.2024 -0.0133 0.0084 0.028 Uiso 1 1 calc R . .
C20 C -0.1626(15) 0.1135(14) 0.0691(9) 0.019(4) Uani 1 1 d . . .
H20 H -0.2190 0.1860 0.0305 0.023 Uiso 1 1 calc R . .
C21 C -0.0891(15) 0.1265(14) 0.1392(9) 0.018(3) Uani 1 1 d . . .
C22 C -0.0043(16) 0.3078(14) 0.1303(10) 0.022(4) Uani 1 1 d . . .
C23 C -0.1340(17) 0.4900(15) 0.1895(9) 0.022(4) Uani 1 1 d . . .
C24 C -0.2160(17) 0.6724(14) 0.2490(11) 0.029(4) Uani 1 1 d . . .
H24A H -0.3123 0.7041 0.2216 0.044 Uiso 1 1 calc R . .
H24B H -0.1855 0.7435 0.2582 0.044 Uiso 1 1 calc R . .
H24C H -0.2166 0.6171 0.3040 0.044 Uiso 1 1 calc R . .
O9 O 0.6751(11) 0.4638(10) 0.4400(6) 0.029(3) Uani 1 1 d . . .
H9 H 0.6179 0.5370 0.4255 0.044 Uiso 1 1 calc R . .
C25 C 0.7505(17) 0.2573(15) 0.4064(11) 0.032(4) Uani 1 1 d . . .
H25A H 0.8303 0.2744 0.3746 0.048 Uiso 1 1 calc R . .
H25B H 0.7188 0.1962 0.3826 0.048 Uiso 1 1 calc R . .
H25C H 0.7817 0.2227 0.4665 0.048 Uiso 1 1 calc R . .
C26 C 0.6284(16) 0.3781(15) 0.3996(10) 0.028(4) Uani 1 1 d . . .
H26A H 0.5999 0.4163 0.3389 0.034 Uiso 1 1 calc R . .
H26B H 0.5449 0.3608 0.4282 0.034 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
S1 C3 1.683(14) . ?
S2 C10 1.684(16) . ?
S3 C15 1.660(16) . ?
S4 C22 1.704(16) . ?
O1 C2 1.215(16) . ?
O2 C2 1.315(17) . ?
O2 C1 1.435(17) . ?
O3 C11 1.208(17) . ?
O4 C11 1.325(18) . ?
O4 C12 1.438(19) . ?
O5 C14 1.209(19) . ?
O6 C14 1.338(19) . ?
O6 C13 1.427(18) . ?
O7 C23 1.198(17) . ?
O8 C23 1.344(19) . ?
O8 C24 1.47(2) . ?
N1 C3 1.381(19) . ?
N1 C2 1.385(18) . ?
N1 H1 0.8800 . ?
N2 C3 1.341(18) . ?
N2 C4 1.432(18) . ?
N2 H2 0.8800 . ?
N3 C10 1.317(19) . ?
N3 C9 1.40(2) . ?
N3 H3 0.8800 . ?
N4 C11 1.372(18) . ?
N4 C10 1.392(19) . ?
N4 H4 0.8800 . ?
N5 C14 1.37(2) . ?
N5 C15 1.39(2) . ?
N5 H5 0.8800 . ?
N6 C15 1.36(2) . ?
N6 C16 1.414(18) . ?
N6 H6 0.8800 . ?
N7 C22 1.331(19) . ?
N7 C21 1.427(18) . ?
N7 H7 0.8800 . ?
N8 C22 1.367(19) . ?
N8 C23 1.39(2) . ?
N8 H8 0.8800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.34(2) . ?
C4 C9 1.39(2) . ?
C5 C6 1.41(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.36(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.40(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.41(2) . ?
C8 H8A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 C21 1.39(2) . ?
C16 C17 1.41(2) . ?
C17 C18 1.40(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.39(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.37(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.40(2) . ?
C20 H20 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O9 C26 1.448(19) . ?
O9 H9 0.8400 . ?
C25 C26 1.51(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 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
C2 O2 C1 117.2(11) . . ?
C11 O4 C12 115.3(12) . . ?
C14 O6 C13 117.3(13) . . ?
C23 O8 C24 113.9(12) . . ?
C3 N1 C2 127.3(13) . . ?
C3 N1 H1 116.4 . . ?
C2 N1 H1 116.4 . . ?
C3 N2 C4 122.8(12) . . ?
C3 N2 H2 118.6 . . ?
C4 N2 H2 118.6 . . ?
C10 N3 C9 128.3(13) . . ?
C10 N3 H3 115.8 . . ?
C9 N3 H3 115.8 . . ?
C11 N4 C10 127.1(13) . . ?
C11 N4 H4 116.4 . . ?
C10 N4 H4 116.4 . . ?
C14 N5 C15 128.0(14) . . ?
C14 N5 H5 116.0 . . ?
C15 N5 H5 116.0 . . ?
C15 N6 C16 125.4(13) . . ?
C15 N6 H6 117.3 . . ?
C16 N6 H6 117.3 . . ?
C22 N7 C21 123.6(12) . . ?
C22 N7 H7 118.2 . . ?
C21 N7 H7 118.2 . . ?
C22 N8 C23 124.2(14) . . ?
C22 N8 H8 117.9 . . ?
C23 N8 H8 117.9 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.7(13) . . ?
O1 C2 N1 124.1(13) . . ?
O2 C2 N1 111.2(13) . . ?
N2 C3 N1 117.8(12) . . ?
N2 C3 S1 123.5(12) . . ?
N1 C3 S1 118.7(11) . . ?
C5 C4 C9 122.3(14) . . ?
C5 C4 N2 120.1(14) . . ?
C9 C4 N2 117.5(13) . . ?
C4 C5 C6 121.7(15) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C7 C6 C5 116.9(14) . . ?
C7 C6 H6A 121.6 . . ?
C5 C6 H6A 121.6 . . ?
C6 C7 C8 122.7(15) . . ?
C6 C7 H7A 118.7 . . ?
C8 C7 H7A 118.7 . . ?
C7 C8 C9 118.6(16) . . ?
C7 C8 H8A 120.7 . . ?
C9 C8 H8A 120.7 . . ?
C4 C9 N3 121.5(13) . . ?
C4 C9 C8 117.7(15) . . ?
N3 C9 C8 120.5(16) . . ?
N3 C10 N4 117.0(13) . . ?
N3 C10 S2 124.2(12) . . ?
N4 C10 S2 118.8(11) . . ?
O3 C11 O4 123.8(14) . . ?
O3 C11 N4 126.3(14) . . ?
O4 C11 N4 109.8(12) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 124.3(15) . . ?
O5 C14 N5 125.9(15) . . ?
O6 C14 N5 109.8(15) . . ?
N6 C15 N5 115.0(13) . . ?
N6 C15 S3 125.7(13) . . ?
N5 C15 S3 119.4(13) . . ?
C21 C16 C17 118.6(13) . . ?
C21 C16 N6 118.6(13) . . ?
C17 C16 N6 122.4(13) . . ?
C18 C17 C16 120.7(13) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 118.6(15) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C20 C19 C18 121.8(15) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 119.5(13) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 120.7(14) . . ?
C16 C21 N7 120.0(13) . . ?
C20 C21 N7 119.2(12) . . ?
N7 C22 N8 120.6(13) . . ?
N7 C22 S4 120.8(12) . . ?
N8 C22 S4 118.6(12) . . ?
O7 C23 O8 125.5(15) . . ?
O7 C23 N8 126.5(15) . . ?
O8 C23 N8 108.0(14) . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 O9 H9 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O9 C26 C25 108.4(12) . . ?
O9 C26 H26A 110.0 . . ?
C25 C26 H26A 110.0 . . ?
O9 C26 H26B 110.0 . . ?
C25 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 7(2) . . . . ?
C1 O2 C2 N1 -174.1(11) . . . . ?
C3 N1 C2 O1 3(2) . . . . ?
C3 N1 C2 O2 -176.3(13) . . . . ?
C4 N2 C3 N1 -179.3(13) . . . . ?
C4 N2 C3 S1 1(2) . . . . ?
C2 N1 C3 N2 2(2) . . . . ?
C2 N1 C3 S1 -178.4(11) . . . . ?
C3 N2 C4 C5 -106.6(16) . . . . ?
C3 N2 C4 C9 74.8(18) . . . . ?
C9 C4 C5 C6 1(2) . . . . ?
N2 C4 C5 C6 -177.6(12) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C5 C6 C7 C8 3(2) . . . . ?
C6 C7 C8 C9 -4(2) . . . . ?
C5 C4 C9 N3 -175.3(13) . . . . ?
N2 C4 C9 N3 3.3(19) . . . . ?
C5 C4 C9 C8 -1(2) . . . . ?
N2 C4 C9 C8 177.3(12) . . . . ?
C10 N3 C9 C4 116.7(17) . . . . ?
C10 N3 C9 C8 -57(2) . . . . ?
C7 C8 C9 C4 2.7(19) . . . . ?
C7 C8 C9 N3 176.7(12) . . . . ?
C9 N3 C10 N4 -170.9(13) . . . . ?
C9 N3 C10 S2 8(2) . . . . ?
C11 N4 C10 N3 3(2) . . . . ?
C11 N4 C10 S2 -176.4(11) . . . . ?
C12 O4 C11 O3 -6(2) . . . . ?
C12 O4 C11 N4 176.5(12) . . . . ?
C10 N4 C11 O3 -1(2) . . . . ?
C10 N4 C11 O4 176.4(12) . . . . ?
C13 O6 C14 O5 3(2) . . . . ?
C13 O6 C14 N5 -177.4(13) . . . . ?
C15 N5 C14 O5 4(3) . . . . ?
C15 N5 C14 O6 -175.3(13) . . . . ?
C16 N6 C15 N5 -177.2(13) . . . . ?
C16 N6 C15 S3 1(2) . . . . ?
C14 N5 C15 N6 -5(2) . . . . ?
C14 N5 C15 S3 176.8(12) . . . . ?
C15 N6 C16 C21 122.8(16) . . . . ?
C15 N6 C16 C17 -63(2) . . . . ?
C21 C16 C17 C18 -1(2) . . . . ?
N6 C16 C17 C18 -174.9(13) . . . . ?
C16 C17 C18 C19 -1(2) . . . . ?
C17 C18 C19 C20 1(2) . . . . ?
C18 C19 C20 C21 0(2) . . . . ?
C17 C16 C21 C20 3(2) . . . . ?
N6 C16 C21 C20 176.8(13) . . . . ?
C17 C16 C21 N7 179.2(13) . . . . ?
N6 C16 C21 N7 -7(2) . . . . ?
C19 C20 C21 C16 -2(2) . . . . ?
C19 C20 C21 N7 -179.0(13) . . . . ?
C22 N7 C21 C16 84.2(18) . . . . ?
C22 N7 C21 C20 -99.3(17) . . . . ?
C21 N7 C22 N8 179.6(12) . . . . ?
C21 N7 C22 S4 3.0(19) . . . . ?
C23 N8 C22 N7 6(2) . . . . ?
C23 N8 C22 S4 -176.9(10) . . . . ?
C24 O8 C23 O7 6(2) . . . . ?
C24 O8 C23 N8 -172.8(11) . . . . ?
C22 N8 C23 O7 -1(2) . . . . ?
C22 N8 C23 O8 177.6(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S4 0.88 2.40 3.284(12) 177.4 .
N2 H2 O1 0.88 2.00 2.680(14) 133.0 .
N3 H3 O3 0.88 2.00 2.699(17) 135.6 .
N3 H3 S1 0.88 2.89 3.475(12) 125.8 .
N6 H6 O5 0.88 1.97 2.677(16) 136.9 .
N7 H7 O7 0.88 2.02 2.682(15) 131.5 .
N8 H8 S1 0.88 2.48 3.355(13) 177.0 .
O9 H9 S2 0.84 2.44 3.275(11) 171.4 .
N2 H2 O7 0.88 2.24 2.945(15) 136.6 1_655
N4 H4 O9 0.88 1.93 2.777(16) 160.4 2_666
N5 H5 S3 0.88 2.65 3.450(14) 151.8 2_556
N7 H7 O1 0.88 2.25 2.966(16) 138.7 1_455

_diffrn_measured_fraction_theta_max 0.843
_diffrn_reflns_theta_full        57.52
_diffrn_measured_fraction_theta_full 0.843
_refine_diff_density_max         1.966
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.261

data_TM_acetone
_database_code_depnum_ccdc_archive 'CCDC 724467'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H14 N4 O4 S2), C3 H6 O'
_chemical_formula_sum            'C27 H34 N8 O9 S4'
_chemical_formula_weight         742.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.206(2)
_cell_length_b                   11.153(2)
_cell_length_c                   17.062(3)
_cell_angle_alpha                76.69(3)
_cell_angle_beta                 86.07(3)
_cell_angle_gamma                72.46(3)
_cell_volume                     1802.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    2.936
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5913
_exptl_absorpt_correction_T_max  0.7578
_exptl_absorpt_process_details   
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8844
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         66.81
_reflns_number_total             6210
_reflns_number_gt                5373
_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 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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0747P)²+1.0993P] 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         6210
_refine_ls_number_parameters     463
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34639(6) 0.79784(6) 0.39508(4) 0.03230(18) Uani 1 1 d . . .
S2 S 0.58300(7) 1.17053(7) 0.14563(4) 0.03700(18) Uani 1 1 d . . .
S3 S 0.27931(6) 0.44635(6) 0.41444(4) 0.02942(17) Uani 1 1 d . . .
S4 S 0.06058(7) 0.26081(7) 0.15085(4) 0.03580(18) Uani 1 1 d . . .
O1 O 0.74152(18) 0.56613(17) 0.29218(12) 0.0343(4) Uani 1 1 d . . .
O2 O 0.62131(18) 0.42391(16) 0.30207(12) 0.0333(4) Uani 1 1 d . . .
O3 O 0.3052(3) 0.9093(2) 0.18248(14) 0.0572(6) Uani 1 1 d . . .
O4 O 0.2646(2) 0.9991(2) 0.05043(13) 0.0551(6) Uani 1 1 d . . .
O5 O -0.10347(18) 0.74963(16) 0.29353(11) 0.0330(4) Uani 1 1 d . . .
O6 O 0.01783(18) 0.88455(16) 0.30162(11) 0.0326(4) Uani 1 1 d . . .
O7 O 0.3352(2) 0.4864(2) 0.20680(12) 0.0499(6) Uani 1 1 d . . .
O8 O 0.3667(2) 0.51941(19) 0.07236(11) 0.0412(5) Uani 1 1 d . . .
N1 N 0.5225(2) 0.60371(19) 0.34404(13) 0.0284(5) Uani 1 1 d D . .
H1N H 0.454(2) 0.570(3) 0.3565(17) 0.034 Uiso 1 1 d D . .
N2 N 0.6046(2) 0.77482(18) 0.34778(12) 0.0239(4) Uani 1 1 d D . .
H2N H 0.685(2) 0.732(2) 0.3305(16) 0.029 Uiso 1 1 d D . .
N3 N 0.4621(2) 1.01389(19) 0.24885(13) 0.0282(5) Uani 1 1 d D . .
H3N H 0.411(3) 0.961(2) 0.2536(17) 0.034 Uiso 1 1 d D . .
N4 N 0.3998(2) 1.0658(2) 0.11433(14) 0.0359(5) Uani 1 1 d D . .
H4N H 0.402(3) 1.121(3) 0.0651(13) 0.043 Uiso 1 1 d D . .
N5 N 0.1134(2) 0.67576(18) 0.34800(12) 0.0252(4) Uani 1 1 d D . .
H5N H 0.185(2) 0.701(3) 0.3574(16) 0.030 Uiso 1 1 d D . .
N6 N 0.0281(2) 0.50365(18) 0.35432(12) 0.0239(4) Uani 1 1 d D . .
H6N H -0.044(2) 0.561(2) 0.3296(15) 0.029 Uiso 1 1 d D . .
N7 N 0.1799(2) 0.33256(19) 0.26099(12) 0.0259(4) Uani 1 1 d D . .
H7N H 0.234(3) 0.375(3) 0.2722(16) 0.031 Uiso 1 1 d D . .
N8 N 0.2379(2) 0.3947(2) 0.12739(13) 0.0303(5) Uani 1 1 d D . .
H8N H 0.242(3) 0.375(3) 0.0799(13) 0.036 Uiso 1 1 d D . .
C1 C 0.7340(3) 0.3448(3) 0.26230(18) 0.0361(6) Uani 1 1 d . . .
H1A H 0.7587 0.3983 0.2129 0.054 Uiso 1 1 calc R . .
H1B H 0.7055 0.2755 0.2488 0.054 Uiso 1 1 calc R . .
H1C H 0.8137 0.3073 0.2984 0.054 Uiso 1 1 calc R . .
C2 C 0.6386(2) 0.5331(2) 0.31124(15) 0.0263(5) Uani 1 1 d . . .
C3 C 0.5006(2) 0.7234(2) 0.36078(14) 0.0241(5) Uani 1 1 d . . .
C4 C 0.5984(2) 0.8946(2) 0.36855(14) 0.0229(5) Uani 1 1 d . . .
C5 C 0.6657(3) 0.8905(2) 0.43751(14) 0.0279(5) Uani 1 1 d . . .
H5 H 0.7131 0.8098 0.4705 0.033 Uiso 1 1 calc R . .
C6 C 0.6638(3) 1.0041(2) 0.45829(15) 0.0311(6) Uani 1 1 d . . .
H6 H 0.7104 1.0015 0.5053 0.037 Uiso 1 1 calc R . .
C7 C 0.5935(3) 1.1216(2) 0.41007(15) 0.0302(5) Uani 1 1 d . . .
H7 H 0.5910 1.1995 0.4247 0.036 Uiso 1 1 calc R . .
C8 C 0.5269(3) 1.1263(2) 0.34097(15) 0.0278(5) Uani 1 1 d . . .
H8 H 0.4786 1.2072 0.3085 0.033 Uiso 1 1 calc R . .
C9 C 0.5309(2) 1.0124(2) 0.31897(14) 0.0238(5) Uani 1 1 d . . .
C10 C 0.4777(3) 1.0790(2) 0.17418(15) 0.0291(5) Uani 1 1 d . . .
C11 C 0.3197(3) 0.9848(3) 0.12196(18) 0.0410(7) Uani 1 1 d . . .
C12 C 0.1758(5) 0.9202(5) 0.0494(3) 0.0819(13) Uani 1 1 d . . .
H12A H 0.2233 0.8303 0.0743 0.123 Uiso 1 1 calc R . .
H12B H 0.1522 0.9264 -0.0064 0.123 Uiso 1 1 calc R . .
H12C H 0.0917 0.9504 0.0795 0.123 Uiso 1 1 calc R . .
C13 C -0.0946(3) 0.9912(2) 0.26146(18) 0.0373(6) Uani 1 1 d . . .
H13A H -0.1186 0.9723 0.2119 0.056 Uiso 1 1 calc R . .
H13B H -0.0664 1.0701 0.2481 0.056 Uiso 1 1 calc R . .
H13C H -0.1746 1.0031 0.2972 0.056 Uiso 1 1 calc R . .
C14 C -0.0005(2) 0.7690(2) 0.31274(14) 0.0244(5) Uani 1 1 d . . .
C15 C 0.1323(2) 0.5439(2) 0.37033(14) 0.0229(5) Uani 1 1 d . . .
C16 C 0.0302(2) 0.3705(2) 0.37516(14) 0.0232(5) Uani 1 1 d . . .
C17 C -0.0505(3) 0.3309(2) 0.43811(15) 0.0294(5) Uani 1 1 d . . .
H17 H -0.1012 0.3894 0.4696 0.035 Uiso 1 1 calc R . .
C18 C -0.0570(3) 0.2043(2) 0.45507(16) 0.0345(6) Uani 1 1 d . . .
H18 H -0.1129 0.1764 0.4979 0.041 Uiso 1 1 calc R . .
C19 C 0.0183(3) 0.1194(2) 0.40925(16) 0.0325(6) Uani 1 1 d . . .
H19 H 0.0141 0.0332 0.4211 0.039 Uiso 1 1 calc R . .
C20 C 0.0995(3) 0.1587(2) 0.34645(15) 0.0274(5) Uani 1 1 d . . .
H20 H 0.1529 0.0991 0.3164 0.033 Uiso 1 1 calc R . .
C21 C 0.1029(2) 0.2860(2) 0.32732(14) 0.0239(5) Uani 1 1 d . . .
C22 C 0.1632(2) 0.3301(2) 0.18396(14) 0.0271(5) Uani 1 1 d . . .
C23 C 0.3168(3) 0.4683(3) 0.14174(16) 0.0332(6) Uani 1 1 d . . .
C24 C 0.4628(4) 0.5894(3) 0.0797(2) 0.0534(9) Uani 1 1 d . . .
H24A H 0.4287 0.6419 0.1198 0.080 Uiso 1 1 calc R . .
H24B H 0.4719 0.6456 0.0275 0.080 Uiso 1 1 calc R . .
H24C H 0.5526 0.5280 0.0967 0.080 Uiso 1 1 calc R . .
O100 O 0.2906(2) 0.2986(2) -0.02117(11) 0.0431(5) Uani 1 1 d . . .
C101 C 0.0808(4) 0.3622(5) -0.0918(3) 0.0766(12) Uani 1 1 d . . .
H10A H 0.0538 0.4289 -0.0602 0.115 Uiso 1 1 calc R . .
H10B H 0.0219 0.3055 -0.0776 0.115 Uiso 1 1 calc R . .
H10C H 0.0709 0.4029 -0.1493 0.115 Uiso 1 1 calc R . .
C102 C 0.2268(3) 0.2851(3) -0.07398(16) 0.0346(6) Uani 1 1 d . . .
C103 C 0.2920(5) 0.1918(4) -0.1251(2) 0.0717(11) Uani 1 1 d . . .
H10D H 0.3919 0.1640 -0.1177 0.108 Uiso 1 1 calc R . .
H10E H 0.2699 0.2331 -0.1818 0.108 Uiso 1 1 calc R . .
H10F H 0.2574 0.1167 -0.1096 0.108 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
S1 C3 1.679(2) . ?
S2 C10 1.672(3) . ?
S3 C15 1.672(3) . ?
S4 C22 1.669(2) . ?
O1 C2 1.215(3) . ?
O2 C2 1.326(3) . ?
O2 C1 1.456(3) . ?
O3 C11 1.204(4) . ?
O4 C11 1.335(3) . ?
O4 C12 1.444(4) . ?
O5 C14 1.215(3) . ?
O6 C14 1.326(3) . ?
O6 C13 1.452(3) . ?
O7 C23 1.210(3) . ?
O8 C23 1.330(3) . ?
O8 C24 1.453(3) . ?
N1 C2 1.373(3) . ?
N1 C3 1.378(3) . ?
N1 H1N 0.882(17) . ?
N2 C3 1.335(3) . ?
N2 C4 1.442(3) . ?
N2 H2N 0.886(17) . ?
N3 C10 1.339(3) . ?
N3 C9 1.423(3) . ?
N3 H3N 0.883(17) . ?
N4 C11 1.370(4) . ?
N4 C10 1.396(3) . ?
N4 H4N 0.926(18) . ?
N5 C14 1.368(3) . ?
N5 C15 1.388(3) . ?
N5 H5N 0.898(17) . ?
N6 C15 1.338(3) . ?
N6 C16 1.439(3) . ?
N6 H6N 0.871(17) . ?
N7 C22 1.344(3) . ?
N7 C21 1.422(3) . ?
N7 H7N 0.885(17) . ?
N8 C23 1.377(3) . ?
N8 C22 1.393(3) . ?
N8 H8N 0.884(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.388(3) . ?
C4 C9 1.392(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 C17 1.381(3) . ?
C16 C21 1.397(3) . ?
C17 C18 1.395(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(3) . ?
C20 H20 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O100 C102 1.209(3) . ?
C101 C102 1.490(5) . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C102 C103 1.486(4) . ?
C103 H10D 0.9800 . ?
C103 H10E 0.9800 . ?
C103 H10F 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
C2 O2 C1 115.15(18) . . ?
C11 O4 C12 115.2(3) . . ?
C14 O6 C13 115.21(19) . . ?
C23 O8 C24 114.9(2) . . ?
C2 N1 C3 126.97(19) . . ?
C2 N1 H1N 118.1(19) . . ?
C3 N1 H1N 115.0(19) . . ?
C3 N2 C4 122.8(2) . . ?
C3 N2 H2N 120.3(18) . . ?
C4 N2 H2N 116.6(17) . . ?
C10 N3 C9 125.8(2) . . ?
C10 N3 H3N 116.3(19) . . ?
C9 N3 H3N 117.5(19) . . ?
C11 N4 C10 127.4(2) . . ?
C11 N4 H4N 118.8(19) . . ?
C10 N4 H4N 113.8(19) . . ?
C14 N5 C15 127.30(19) . . ?
C14 N5 H5N 117.6(18) . . ?
C15 N5 H5N 115.1(18) . . ?
C15 N6 C16 123.0(2) . . ?
C15 N6 H6N 118.3(18) . . ?
C16 N6 H6N 118.7(18) . . ?
C22 N7 C21 125.1(2) . . ?
C22 N7 H7N 119.4(18) . . ?
C21 N7 H7N 114.9(18) . . ?
C23 N8 C22 126.8(2) . . ?
C23 N8 H8N 119.5(19) . . ?
C22 N8 H8N 113.0(19) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.7(2) . . ?
O1 C2 N1 125.3(2) . . ?
O2 C2 N1 110.05(19) . . ?
N2 C3 N1 117.4(2) . . ?
N2 C3 S1 123.24(18) . . ?
N1 C3 S1 119.34(16) . . ?
C5 C4 C9 120.4(2) . . ?
C5 C4 N2 118.6(2) . . ?
C9 C4 N2 120.9(2) . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 119.3(2) . . ?
C4 C9 N3 119.3(2) . . ?
C8 C9 N3 121.4(2) . . ?
N3 C10 N4 115.9(2) . . ?
N3 C10 S2 126.73(19) . . ?
N4 C10 S2 117.35(19) . . ?
O3 C11 O4 125.3(3) . . ?
O3 C11 N4 125.8(3) . . ?
O4 C11 N4 108.9(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 124.4(2) . . ?
O5 C14 N5 125.3(2) . . ?
O6 C14 N5 110.26(19) . . ?
N6 C15 N5 116.1(2) . . ?
N6 C15 S3 124.26(17) . . ?
N5 C15 S3 119.61(17) . . ?
C17 C16 C21 120.7(2) . . ?
C17 C16 N6 119.0(2) . . ?
C21 C16 N6 120.0(2) . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 119.3(2) . . ?
C20 C21 N7 121.9(2) . . ?
C16 C21 N7 118.80(19) . . ?
N7 C22 N8 115.5(2) . . ?
N7 C22 S4 126.30(17) . . ?
N8 C22 S4 118.16(19) . . ?
O7 C23 O8 125.1(2) . . ?
O7 C23 N8 125.6(2) . . ?
O8 C23 N8 109.3(2) . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C102 C101 H10A 109.5 . . ?
C102 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C102 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
O100 C102 C103 121.1(3) . . ?
O100 C102 C101 121.9(3) . . ?
C103 C102 C101 117.0(3) . . ?
C102 C103 H10D 109.5 . . ?
C102 C103 H10E 109.5 . . ?
H10D C103 H10E 109.5 . . ?
C102 C103 H10F 109.5 . . ?
H10D C103 H10F 109.5 . . ?
H10E C103 H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 -3.3(4) . . . . ?
C1 O2 C2 N1 175.7(2) . . . . ?
C3 N1 C2 O1 0.5(4) . . . . ?
C3 N1 C2 O2 -178.5(2) . . . . ?
C4 N2 C3 N1 -175.2(2) . . . . ?
C4 N2 C3 S1 5.5(3) . . . . ?
C2 N1 C3 N2 -3.6(4) . . . . ?
C2 N1 C3 S1 175.8(2) . . . . ?
C3 N2 C4 C5 102.6(3) . . . . ?
C3 N2 C4 C9 -79.9(3) . . . . ?
C9 C4 C5 C6 1.3(3) . . . . ?
N2 C4 C5 C6 178.8(2) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C5 C4 C9 C8 -2.5(3) . . . . ?
N2 C4 C9 C8 180.0(2) . . . . ?
C5 C4 C9 N3 -179.7(2) . . . . ?
N2 C4 C9 N3 2.8(3) . . . . ?
C7 C8 C9 C4 2.1(3) . . . . ?
C7 C8 C9 N3 179.2(2) . . . . ?
C10 N3 C9 C4 -128.7(3) . . . . ?
C10 N3 C9 C8 54.2(3) . . . . ?
C9 N3 C10 N4 179.8(2) . . . . ?
C9 N3 C10 S2 1.3(4) . . . . ?
C11 N4 C10 N3 -6.8(4) . . . . ?
C11 N4 C10 S2 171.8(2) . . . . ?
C12 O4 C11 O3 3.1(5) . . . . ?
C12 O4 C11 N4 -179.3(3) . . . . ?
C10 N4 C11 O3 -1.1(5) . . . . ?
C10 N4 C11 O4 -178.6(3) . . . . ?
C13 O6 C14 O5 -1.8(4) . . . . ?
C13 O6 C14 N5 177.6(2) . . . . ?
C15 N5 C14 O5 -1.8(4) . . . . ?
C15 N5 C14 O6 178.8(2) . . . . ?
C16 N6 C15 N5 -178.7(2) . . . . ?
C16 N6 C15 S3 1.4(3) . . . . ?
C14 N5 C15 N6 1.2(4) . . . . ?
C14 N5 C15 S3 -178.88(19) . . . . ?
C15 N6 C16 C17 107.1(3) . . . . ?
C15 N6 C16 C21 -78.9(3) . . . . ?
C21 C16 C17 C18 1.4(4) . . . . ?
N6 C16 C17 C18 175.3(2) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C21 -1.9(4) . . . . ?
C19 C20 C21 C16 3.8(4) . . . . ?
C19 C20 C21 N7 -177.1(2) . . . . ?
C17 C16 C21 C20 -3.6(4) . . . . ?
N6 C16 C21 C20 -177.5(2) . . . . ?
C17 C16 C21 N7 177.3(2) . . . . ?
N6 C16 C21 N7 3.4(3) . . . . ?
C22 N7 C21 C20 58.3(4) . . . . ?
C22 N7 C21 C16 -122.7(3) . . . . ?
C21 N7 C22 N8 172.5(2) . . . . ?
C21 N7 C22 S4 -6.0(4) . . . . ?
C23 N8 C22 N7 -5.6(4) . . . . ?
C23 N8 C22 S4 173.1(2) . . . . ?
C24 O8 C23 O7 7.4(4) . . . . ?
C24 O8 C23 N8 -174.3(3) . . . . ?
C22 N8 C23 O7 1.3(5) . . . . ?
C22 N8 C23 O8 -177.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N S3 0.882(17) 2.582(18) 3.454(2) 170(3) .
N2 H2N O1 0.886(17) 2.01(2) 2.673(3) 131(2) .
N2 H2N O5 0.886(17) 2.26(2) 3.009(3) 142(2) 1_655
N3 H3N O3 0.883(17) 1.96(2) 2.681(3) 137(3) .
N3 H3N S1 0.883(17) 2.84(3) 3.459(2) 129(2) .
N4 H4N O100 0.926(18) 2.22(2) 3.029(3) 146(3) 1_565
N5 H5N S1 0.898(17) 2.412(18) 3.297(2) 169(2) .
N6 H6N O5 0.871(17) 1.97(2) 2.658(3) 135(2) .
N6 H6N O1 0.871(17) 2.30(2) 3.003(3) 137(2) 1_455
N7 H7N O7 0.885(17) 1.96(2) 2.649(3) 134(2) .
N7 H7N S3 0.885(17) 2.83(2) 3.488(2) 133(2) .
N8 H8N O100 0.884(17) 2.059(19) 2.929(3) 168(3) .

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        66.81
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.068

data_TM_cyclohexanone
_database_code_depnum_ccdc_archive 'CCDC 724468'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, cyclohexanone'
_chemical_melting_point          ?
_chemical_formula_moiety         '2 C12 H14 N4 O4 S2, C6 H10 O'
_chemical_formula_sum            'C60 H76 N16 O18 S8'
_chemical_formula_weight         1565.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   11.277(3)
_cell_length_b                   17.368(4)
_cell_length_c                   19.902(5)
_cell_angle_alpha                92.210(12)
_cell_angle_beta                 103.760(11)
_cell_angle_gamma                100.772(10)
_cell_volume                     3705.2(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1640
_exptl_absorpt_coefficient_mu    2.885
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3265
_exptl_absorpt_correction_T_max  0.4782
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28524
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         57.68
_reflns_number_total             9162
_reflns_number_gt                6713
_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 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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0449P)²+0.9447P] 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     SHELXL
_refine_ls_extinction_coef       0.00030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9162
_refine_ls_number_parameters     976
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33365(7) 0.07390(5) 0.90681(4) 0.0255(2) Uani 1 1 d . . .
S2 S 0.02420(7) 0.32733(5) 0.80680(4) 0.0282(2) Uani 1 1 d . . .
S3 S 0.31630(7) 0.66424(5) 0.41196(4) 0.0272(2) Uani 1 1 d . . .
S4 S 0.77952(7) 0.89397(5) 0.57147(4) 0.0275(2) Uani 1 1 d . . .
S5 S 0.53163(8) 0.33952(5) 0.30888(4) 0.0310(2) Uani 1 1 d . . .
S6 S 0.84248(7) 0.09683(5) 0.39683(4) 0.0257(2) Uani 1 1 d . . .
S7 S 1.21396(8) 0.35300(5) 0.06867(4) 0.0302(2) Uani 1 1 d . . .
S8 S 0.72153(7) 0.09834(5) -0.06544(4) 0.0294(2) Uani 1 1 d . . .
O1 O 0.62809(19) 0.17622(12) 0.77773(10) 0.0256(5) Uani 1 1 d . . .
O2 O 0.43329(19) 0.17945(12) 0.71535(11) 0.0259(5) Uani 1 1 d . . .
O3 O 0.38963(19) 0.27750(13) 0.93750(11) 0.0351(6) Uani 1 1 d . . .
O4 O 0.4341(2) 0.40983(12) 0.95636(11) 0.0344(6) Uani 1 1 d . . .
O5 O 0.64081(19) 0.55754(12) 0.55681(11) 0.0301(6) Uani 1 1 d . . .
O6 O 0.7027(2) 0.68953(14) 0.55856(12) 0.0411(7) Uani 1 1 d . . .
O7 O 1.02487(19) 0.82234(12) 0.42207(10) 0.0249(5) Uani 1 1 d . . .
O8 O 0.83367(19) 0.82969(12) 0.35773(11) 0.0260(5) Uani 1 1 d . . .
O9 O 0.88984(19) 0.42290(12) 0.50080(11) 0.0290(6) Uani 1 1 d . . .
O10 O 0.8707(2) 0.29396(13) 0.46896(11) 0.0340(6) Uani 1 1 d . . .
O11 O 0.95443(19) 0.21211(12) 0.21229(11) 0.0265(5) Uani 1 1 d . . .
O12 O 1.14637(19) 0.20124(12) 0.27358(10) 0.0258(5) Uani 1 1 d . . .
O13 O 0.88768(19) 0.44730(12) -0.08548(11) 0.0350(6) Uani 1 1 d . . .
O14 O 0.8189(2) 0.31944(14) -0.07165(12) 0.0376(6) Uani 1 1 d . . .
O15 O 0.48814(19) 0.19572(12) 0.07939(10) 0.0255(5) Uani 1 1 d . . .
O16 O 0.6925(2) 0.22130(12) 0.13511(11) 0.0276(6) Uani 1 1 d . . .
O17 O 0.3035(2) 0.46638(12) 0.58414(11) 0.0337(6) Uani 1 1 d . . .
O18 O 0.82203(19) 0.49108(12) 0.08556(11) 0.0283(6) Uani 1 1 d . . .
N1 N 0.4715(2) 0.13222(14) 0.82372(13) 0.0210(6) Uani 1 1 d D . .
H1 H 0.538(2) 0.1259(16) 0.8563(12) 0.025 Uiso 1 1 d D . .
N2 N 0.2589(2) 0.12369(14) 0.78148(13) 0.0207(6) Uani 1 1 d D . .
H2 H 0.279(3) 0.1440(16) 0.7441(12) 0.025 Uiso 1 1 d D . .
N3 N 0.1623(2) 0.22238(15) 0.85898(13) 0.0202(6) Uani 1 1 d D . .
H3 H 0.2358(19) 0.2159(16) 0.8855(13) 0.024 Uiso 1 1 d D . .
N4 N 0.2446(2) 0.35287(15) 0.89492(13) 0.0246(7) Uani 1 1 d D . .
H4 H 0.231(3) 0.4023(12) 0.8968(15) 0.030 Uiso 1 1 d D . .
N5 N 0.5055(3) 0.62479(15) 0.49959(14) 0.0243(7) Uani 1 1 d D . .
H5 H 0.452(2) 0.5780(12) 0.4862(14) 0.029 Uiso 1 1 d D . .
N6 N 0.5196(2) 0.75912(15) 0.49337(13) 0.0229(7) Uani 1 1 d D . .
H6 H 0.5949(19) 0.7646(17) 0.5216(13) 0.028 Uiso 1 1 d D . .
N7 N 0.6835(2) 0.86392(14) 0.43520(13) 0.0202(6) Uani 1 1 d D . .
H7 H 0.700(3) 0.8512(16) 0.3949(11) 0.024 Uiso 1 1 d D . .
N8 N 0.8921(2) 0.85807(15) 0.47634(13) 0.0223(7) Uani 1 1 d D . .
H8 H 0.954(2) 0.8607(17) 0.5132(11) 0.027 Uiso 1 1 d D . .
N9 N 0.7306(2) 0.36675(15) 0.41396(13) 0.0229(7) Uani 1 1 d D . .
H9 H 0.714(3) 0.4156(12) 0.4125(15) 0.027 Uiso 1 1 d D . .
N10 N 0.6696(2) 0.23755(15) 0.36540(12) 0.0204(6) Uani 1 1 d D . .
H10 H 0.735(2) 0.2271(17) 0.3968(12) 0.024 Uiso 1 1 d D . .
N11 N 0.7762(2) 0.15760(14) 0.27620(13) 0.0210(6) Uani 1 1 d D . .
H11 H 0.801(3) 0.1797(16) 0.2421(12) 0.025 Uiso 1 1 d D . .
N12 N 0.9876(2) 0.16309(15) 0.31983(13) 0.0216(6) Uani 1 1 d D . .
H12 H 1.048(2) 0.1482(16) 0.3508(12) 0.026 Uiso 1 1 d D . .
N13 N 1.0177(3) 0.38620(15) -0.01728(14) 0.0254(7) Uani 1 1 d D . .
H13 H 1.072(2) 0.4305(12) -0.0129(15) 0.030 Uiso 1 1 d D . .
N14 N 0.9982(2) 0.25566(16) 0.00393(13) 0.0234(7) Uani 1 1 d D . .
H14 H 0.9195(18) 0.2499(17) -0.0230(13) 0.028 Uiso 1 1 d D . .
N15 N 0.8314(2) 0.15781(14) 0.06368(13) 0.0208(6) Uani 1 1 d D . .
H15 H 0.822(3) 0.1794(15) 0.1026(11) 0.025 Uiso 1 1 d D . .
N16 N 0.6184(2) 0.15457(15) 0.02625(13) 0.0231(7) Uani 1 1 d D . .
H16 H 0.547(2) 0.1392(16) -0.0064(12) 0.028 Uiso 1 1 d D . .
C1 C 0.6778(3) 0.21453(19) 0.72404(16) 0.0301(9) Uani 1 1 d . . .
H1A H 0.6608 0.1770 0.6832 0.045 Uiso 1 1 calc R . .
H1B H 0.7680 0.2332 0.7414 0.045 Uiso 1 1 calc R . .
H1C H 0.6381 0.2593 0.7112 0.045 Uiso 1 1 calc R . .
C2 C 0.5050(3) 0.16431(17) 0.76691(18) 0.0226(8) Uani 1 1 d . . .
C3 C 0.3527(3) 0.11201(17) 0.83317(16) 0.0217(8) Uani 1 1 d . . .
C4 C 0.1303(3) 0.10539(18) 0.78230(15) 0.0203(8) Uani 1 1 d . . .
C5 C 0.0530(3) 0.04066(18) 0.74164(16) 0.0252(8) Uani 1 1 d . . .
H5A H 0.0868 0.0068 0.7161 0.030 Uiso 1 1 calc R . .
C6 C -0.0740(3) 0.02464(18) 0.73779(16) 0.0257(8) Uani 1 1 d . . .
H6A H -0.1270 -0.0195 0.7091 0.031 Uiso 1 1 calc R . .
C7 C -0.1228(3) 0.07316(18) 0.77580(16) 0.0235(8) Uani 1 1 d . . .
H7A H -0.2094 0.0622 0.7737 0.028 Uiso 1 1 calc R . .
C8 C -0.0452(3) 0.13803(17) 0.81705(15) 0.0219(8) Uani 1 1 d . . .
H8A H -0.0787 0.1708 0.8438 0.026 Uiso 1 1 calc R . .
C9 C 0.0804(3) 0.15523(18) 0.81938(15) 0.0200(8) Uani 1 1 d . . .
C10 C 0.1471(3) 0.29706(19) 0.85495(15) 0.0225(8) Uani 1 1 d . . .
C11 C 0.3594(3) 0.3404(2) 0.93092(16) 0.0284(9) Uani 1 1 d . . .
C12 C 0.5569(3) 0.4048(2) 0.99739(19) 0.0517(11) Uani 1 1 d . . .
H12A H 0.5504 0.3862 1.0425 0.078 Uiso 1 1 calc R . .
H12B H 0.6117 0.4569 1.0045 0.078 Uiso 1 1 calc R . .
H12C H 0.5915 0.3679 0.9729 0.078 Uiso 1 1 calc R . .
C13 C 0.7672(3) 0.5574(2) 0.59755(19) 0.0484(11) Uani 1 1 d . . .
H13A H 0.8270 0.5759 0.5703 0.073 Uiso 1 1 calc R . .
H13B H 0.7734 0.5038 0.6095 0.073 Uiso 1 1 calc R . .
H13C H 0.7859 0.5922 0.6402 0.073 Uiso 1 1 calc R . .
C14 C 0.6252(4) 0.6301(2) 0.54078(17) 0.0288(9) Uani 1 1 d . . .
C15 C 0.4529(3) 0.68696(19) 0.47084(15) 0.0229(8) Uani 1 1 d . . .
C16 C 0.4850(3) 0.82980(17) 0.46809(15) 0.0202(8) Uani 1 1 d . . .
C17 C 0.3724(3) 0.84840(17) 0.47207(15) 0.0228(8) Uani 1 1 d . . .
H17 H 0.3178 0.8145 0.4929 0.027 Uiso 1 1 calc R . .
C18 C 0.3393(3) 0.91609(18) 0.44587(15) 0.0224(8) Uani 1 1 d . . .
H18 H 0.2619 0.9285 0.4485 0.027 Uiso 1 1 calc R . .
C19 C 0.4189(3) 0.96564(18) 0.41590(16) 0.0242(8) Uani 1 1 d . . .
H19 H 0.3952 1.0115 0.3970 0.029 Uiso 1 1 calc R . .
C20 C 0.5329(3) 0.94862(18) 0.41330(15) 0.0231(8) Uani 1 1 d . . .
H20 H 0.5882 0.9832 0.3934 0.028 Uiso 1 1 calc R . .
C21 C 0.5662(3) 0.88081(17) 0.43996(15) 0.0191(8) Uani 1 1 d . . .
C22 C 0.7826(3) 0.87136(17) 0.48911(16) 0.0207(8) Uani 1 1 d . . .
C23 C 0.9103(3) 0.83615(17) 0.41303(18) 0.0220(8) Uani 1 1 d . . .
C24 C 1.0531(3) 0.79141(18) 0.36019(16) 0.0282(9) Uani 1 1 d . . .
H24A H 0.9838 0.7495 0.3355 0.042 Uiso 1 1 calc R . .
H24B H 1.1293 0.7702 0.3734 0.042 Uiso 1 1 calc R . .
H24C H 1.0655 0.8337 0.3298 0.042 Uiso 1 1 calc R . .
C25 C 0.9940(3) 0.41656(19) 0.55761(17) 0.0392(10) Uani 1 1 d . . .
H25A H 0.9657 0.3780 0.5881 0.059 Uiso 1 1 calc R . .
H25B H 1.0279 0.4679 0.5841 0.059 Uiso 1 1 calc R . .
H25C H 1.0589 0.3994 0.5391 0.059 Uiso 1 1 calc R . .
C26 C 0.8344(3) 0.3549(2) 0.46241(16) 0.0249(8) Uani 1 1 d . . .
C27 C 0.6479(3) 0.31054(19) 0.36452(16) 0.0225(8) Uani 1 1 d . . .
C28 C 0.5936(3) 0.17380(17) 0.31774(16) 0.0201(8) Uani 1 1 d . . .
C29 C 0.4678(3) 0.15069(17) 0.31418(16) 0.0226(8) Uani 1 1 d . . .
H29 H 0.4318 0.1758 0.3452 0.027 Uiso 1 1 calc R . .
C30 C 0.3946(3) 0.09124(18) 0.26568(17) 0.0269(8) Uani 1 1 d . . .
H30 H 0.3079 0.0765 0.2626 0.032 Uiso 1 1 calc R . .
C31 C 0.4471(3) 0.05301(18) 0.22158(17) 0.0293(9) Uani 1 1 d . . .
H31 H 0.3964 0.0124 0.1880 0.035 Uiso 1 1 calc R . .
C32 C 0.5736(3) 0.07406(18) 0.22649(16) 0.0260(8) Uani 1 1 d . . .
H32 H 0.6101 0.0471 0.1968 0.031 Uiso 1 1 calc R . .
C33 C 0.6473(3) 0.13436(17) 0.27458(16) 0.0185(8) Uani 1 1 d . . .
C34 C 0.8674(3) 0.14151(17) 0.32693(16) 0.0223(8) Uani 1 1 d . . .
C35 C 1.0241(3) 0.19404(17) 0.26341(17) 0.0238(8) Uani 1 1 d . . .
C36 C 1.1978(3) 0.23267(19) 0.21767(16) 0.0286(9) Uani 1 1 d . . .
H36A H 1.1754 0.1926 0.1783 0.043 Uiso 1 1 calc R . .
H36B H 1.2888 0.2475 0.2339 0.043 Uiso 1 1 calc R . .
H36C H 1.1640 0.2791 0.2030 0.043 Uiso 1 1 calc R . .
C37 C 0.7734(3) 0.4442(2) -0.13804(18) 0.0461(11) Uani 1 1 d . . .
H37A H 0.7675 0.4050 -0.1761 0.069 Uiso 1 1 calc R . .
H37B H 0.7730 0.4960 -0.1560 0.069 Uiso 1 1 calc R . .
H37C H 0.7021 0.4296 -0.1177 0.069 Uiso 1 1 calc R . .
C38 C 0.8994(4) 0.3780(2) -0.05980(17) 0.0309(9) Uani 1 1 d . . .
C39 C 1.0714(3) 0.32778(19) 0.01689(16) 0.0251(8) Uani 1 1 d . . .
C40 C 1.0302(3) 0.18518(17) 0.03091(15) 0.0201(8) Uani 1 1 d . . .
C41 C 1.1403(3) 0.16303(18) 0.02640(15) 0.0241(8) Uani 1 1 d . . .
H41 H 1.1974 0.1958 0.0063 0.029 Uiso 1 1 calc R . .
C42 C 1.1670(3) 0.09319(18) 0.05120(15) 0.0241(8) Uani 1 1 d . . .
H42 H 1.2427 0.0782 0.0485 0.029 Uiso 1 1 calc R . .
C43 C 1.0836(3) 0.04563(18) 0.07982(16) 0.0251(8) Uani 1 1 d . . .
H43 H 1.1024 -0.0021 0.0971 0.030 Uiso 1 1 calc R . .
C44 C 0.9730(3) 0.06646(18) 0.08371(15) 0.0229(8) Uani 1 1 d . . .
H44 H 0.9156 0.0331 0.1032 0.027 Uiso 1 1 calc R . .
C45 C 0.9462(3) 0.13652(18) 0.05891(15) 0.0182(8) Uani 1 1 d . . .
C46 C 0.7263(3) 0.13880(17) 0.01306(16) 0.0215(8) Uani 1 1 d . . .
C47 C 0.6063(3) 0.19309(18) 0.08536(18) 0.0225(8) Uani 1 1 d . . .
C48 C 0.4623(3) 0.23847(18) 0.13681(16) 0.0288(9) Uani 1 1 d . . .
H48A H 0.4827 0.2112 0.1790 0.043 Uiso 1 1 calc R . .
H48B H 0.3738 0.2411 0.1258 0.043 Uiso 1 1 calc R . .
H48C H 0.5130 0.2919 0.1444 0.043 Uiso 1 1 calc R . .
C49 C 0.4943(3) 0.46233(19) 0.66736(16) 0.0282(9) Uani 1 1 d . . .
H49A H 0.5216 0.5166 0.6557 0.034 Uiso 1 1 calc R . .
H49B H 0.5515 0.4298 0.6561 0.034 Uiso 1 1 calc R . .
C50 C 0.4981(3) 0.46251(19) 0.74472(16) 0.0328(9) Uani 1 1 d . . .
H50A H 0.5851 0.4814 0.7723 0.039 Uiso 1 1 calc R . .
H50B H 0.4474 0.4993 0.7564 0.039 Uiso 1 1 calc R . .
C51 C 0.4491(3) 0.38138(19) 0.76378(17) 0.0351(9) Uani 1 1 d . . .
H51A H 0.4499 0.3840 0.8137 0.042 Uiso 1 1 calc R . .
H51B H 0.5042 0.3456 0.7560 0.042 Uiso 1 1 calc R . .
C52 C 0.3168(3) 0.34871(19) 0.72068(16) 0.0329(9) Uani 1 1 d . . .
H52A H 0.2599 0.3812 0.7324 0.040 Uiso 1 1 calc R . .
H52B H 0.2890 0.2944 0.7321 0.040 Uiso 1 1 calc R . .
C53 C 0.3101(3) 0.34854(18) 0.64265(17) 0.0335(9) Uani 1 1 d . . .
H53A H 0.3571 0.3102 0.6294 0.040 Uiso 1 1 calc R . .
H53B H 0.2222 0.3326 0.6156 0.040 Uiso 1 1 calc R . .
C54 C 0.3646(3) 0.42968(19) 0.62630(17) 0.0293(9) Uani 1 1 d . . .
C55 C 0.8357(3) 0.45268(18) 0.13596(17) 0.0268(8) Uani 1 1 d . . .
C56 C 0.9324(3) 0.40292(19) 0.15157(16) 0.0310(9) Uani 1 1 d . . .
H56A H 0.9912 0.4159 0.1219 0.037 Uiso 1 1 calc R . .
H56B H 0.8913 0.3468 0.1401 0.037 Uiso 1 1 calc R . .
C57 C 1.0049(3) 0.4153(2) 0.22763(17) 0.0377(10) Uani 1 1 d . . .
H57A H 1.0601 0.3769 0.2370 0.045 Uiso 1 1 calc R . .
H57B H 1.0579 0.4688 0.2371 0.045 Uiso 1 1 calc R . .
C58 C 0.9181(3) 0.4057(2) 0.27574(17) 0.0362(9) Uani 1 1 d . . .
H58A H 0.9677 0.4149 0.3246 0.043 Uiso 1 1 calc R . .
H58B H 0.8685 0.3513 0.2684 0.043 Uiso 1 1 calc R . .
C59 C 0.8308(3) 0.46350(19) 0.26219(16) 0.0346(9) Uani 1 1 d . . .
H59A H 0.8800 0.5180 0.2726 0.042 Uiso 1 1 calc R . .
H59B H 0.7734 0.4555 0.2931 0.042 Uiso 1 1 calc R . .
C60 C 0.7550(3) 0.4516(2) 0.18578(16) 0.0328(9) Uani 1 1 d . . .
H60A H 0.6952 0.4006 0.1780 0.039 Uiso 1 1 calc R . .
H60B H 0.7065 0.4937 0.1765 0.039 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
S1 C3 1.674(3) . ?
S2 C10 1.672(3) . ?
S3 C15 1.667(3) . ?
S4 C22 1.681(3) . ?
S5 C27 1.673(3) . ?
S6 C34 1.675(3) . ?
S7 C39 1.659(3) . ?
S8 C46 1.673(3) . ?
O1 C2 1.328(3) . ?
O1 C1 1.449(3) . ?
O2 C2 1.217(3) . ?
O3 C11 1.207(4) . ?
O4 C11 1.337(4) . ?
O4 C12 1.451(4) . ?
O5 C14 1.345(4) . ?
O5 C13 1.463(4) . ?
O6 C14 1.200(4) . ?
O7 C23 1.329(3) . ?
O7 C24 1.452(3) . ?
O8 C23 1.214(3) . ?
O9 C26 1.340(4) . ?
O9 C25 1.448(3) . ?
O10 C26 1.205(4) . ?
O11 C35 1.219(3) . ?
O12 C35 1.327(3) . ?
O12 C36 1.452(3) . ?
O13 C38 1.343(4) . ?
O13 C37 1.445(4) . ?
O14 C38 1.203(4) . ?
O15 C47 1.319(3) . ?
O15 C48 1.455(3) . ?
O16 C47 1.221(4) . ?
O17 C54 1.231(3) . ?
O18 C55 1.221(3) . ?
N1 C3 1.379(4) . ?
N1 C2 1.380(4) . ?
N2 C3 1.341(4) . ?
N2 C4 1.430(4) . ?
N3 C10 1.343(4) . ?
N3 C9 1.419(4) . ?
N4 C10 1.381(4) . ?
N4 C11 1.382(4) . ?
N5 C14 1.388(4) . ?
N5 C15 1.404(4) . ?
N6 C15 1.335(4) . ?
N6 C16 1.430(4) . ?
N7 C22 1.335(4) . ?
N7 C21 1.431(4) . ?
N8 C23 1.375(4) . ?
N8 C22 1.376(4) . ?
N9 C26 1.383(4) . ?
N9 C27 1.393(4) . ?
N10 C27 1.335(4) . ?
N10 C28 1.428(4) . ?
N11 C34 1.338(4) . ?
N11 C33 1.426(4) . ?
N12 C34 1.379(4) . ?
N12 C35 1.380(4) . ?
N13 C38 1.378(4) . ?
N13 C39 1.394(4) . ?
N14 C39 1.343(4) . ?
N14 C40 1.428(4) . ?
N15 C46 1.337(4) . ?
N15 C45 1.435(4) . ?
N16 C46 1.377(4) . ?
N16 C47 1.378(4) . ?
C4 C5 1.381(4) . ?
C4 C9 1.393(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.381(4) . ?
C16 C21 1.384(4) . ?
C16 C17 1.387(4) . ?
C17 C18 1.383(4) . ?
C18 C19 1.381(4) . ?
C19 C20 1.385(4) . ?
C20 C21 1.388(4) . ?
C28 C29 1.384(4) . ?
C28 C33 1.389(4) . ?
C29 C30 1.380(4) . ?
C30 C31 1.382(4) . ?
C31 C32 1.384(4) . ?
C32 C33 1.386(4) . ?
C40 C45 1.382(4) . ?
C40 C41 1.387(4) . ?
C41 C42 1.385(4) . ?
C42 C43 1.375(4) . ?
C43 C44 1.381(4) . ?
C44 C45 1.388(4) . ?
C49 C54 1.488(4) . ?
C49 C50 1.530(4) . ?
C50 C51 1.512(4) . ?
C51 C52 1.523(4) . ?
C52 C53 1.537(4) . ?
C53 C54 1.509(4) . ?
C55 C60 1.495(4) . ?
C55 C56 1.498(4) . ?
C56 C57 1.525(4) . ?
C57 C58 1.516(4) . ?
C58 C59 1.520(4) . ?
C59 C60 1.542(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
C2 O1 C1 115.2(2) . . ?
C11 O4 C12 114.7(3) . . ?
C14 O5 C13 112.3(3) . . ?
C23 O7 C24 115.2(2) . . ?
C26 O9 C25 114.1(2) . . ?
C35 O12 C36 115.4(2) . . ?
C38 O13 C37 113.9(3) . . ?
C47 O15 C48 115.6(2) . . ?
C3 N1 C2 127.1(3) . . ?
C3 N2 C4 124.4(3) . . ?
C10 N3 C9 125.9(3) . . ?
C10 N4 C11 126.7(3) . . ?
C14 N5 C15 126.7(3) . . ?
C15 N6 C16 124.2(3) . . ?
C22 N7 C21 124.0(3) . . ?
C23 N8 C22 126.5(3) . . ?
C26 N9 C27 126.5(3) . . ?
C27 N10 C28 123.0(3) . . ?
C34 N11 C33 123.1(3) . . ?
C34 N12 C35 127.1(3) . . ?
C38 N13 C39 127.4(3) . . ?
C39 N14 C40 126.2(3) . . ?
C46 N15 C45 123.2(3) . . ?
C46 N16 C47 127.2(3) . . ?
O2 C2 O1 125.6(3) . . ?
O2 C2 N1 125.5(3) . . ?
O1 C2 N1 109.0(3) . . ?
N2 C3 N1 116.9(3) . . ?
N2 C3 S1 124.1(2) . . ?
N1 C3 S1 118.9(2) . . ?
C5 C4 C9 119.7(3) . . ?
C5 C4 N2 119.3(3) . . ?
C9 C4 N2 120.8(3) . . ?
C4 C5 C6 120.5(3) . . ?
C7 C6 C5 119.7(3) . . ?
C6 C7 C8 120.0(3) . . ?
C9 C8 C7 120.4(3) . . ?
C8 C9 C4 119.7(3) . . ?
C8 C9 N3 122.2(3) . . ?
C4 C9 N3 118.1(3) . . ?
N3 C10 N4 115.1(3) . . ?
N3 C10 S2 126.4(3) . . ?
N4 C10 S2 118.5(2) . . ?
O3 C11 O4 124.8(3) . . ?
O3 C11 N4 126.0(3) . . ?
O4 C11 N4 109.2(3) . . ?
O6 C14 O5 125.6(3) . . ?
O6 C14 N5 125.7(3) . . ?
O5 C14 N5 108.7(3) . . ?
N6 C15 N5 115.7(3) . . ?
N6 C15 S3 126.5(2) . . ?
N5 C15 S3 117.8(2) . . ?
C21 C16 C17 119.6(3) . . ?
C21 C16 N6 119.3(3) . . ?
C17 C16 N6 121.1(3) . . ?
C18 C17 C16 120.3(3) . . ?
C19 C18 C17 120.0(3) . . ?
C18 C19 C20 120.2(3) . . ?
C19 C20 C21 119.7(3) . . ?
C16 C21 C20 120.2(3) . . ?
C16 C21 N7 121.3(3) . . ?
C20 C21 N7 118.4(3) . . ?
N7 C22 N8 117.9(3) . . ?
N7 C22 S4 123.5(2) . . ?
N8 C22 S4 118.6(2) . . ?
O8 C23 O7 125.4(3) . . ?
O8 C23 N8 125.5(3) . . ?
O7 C23 N8 109.2(3) . . ?
O10 C26 O9 125.2(3) . . ?
O10 C26 N9 126.0(3) . . ?
O9 C26 N9 108.8(3) . . ?
N10 C27 N9 116.5(3) . . ?
N10 C27 S5 125.5(2) . . ?
N9 C27 S5 118.0(2) . . ?
C29 C28 C33 119.7(3) . . ?
C29 C28 N10 121.0(3) . . ?
C33 C28 N10 119.2(3) . . ?
C30 C29 C28 120.2(3) . . ?
C29 C30 C31 120.2(3) . . ?
C30 C31 C32 119.8(3) . . ?
C31 C32 C33 120.2(3) . . ?
C32 C33 C28 119.8(3) . . ?
C32 C33 N11 119.0(3) . . ?
C28 C33 N11 121.1(3) . . ?
N11 C34 N12 117.0(3) . . ?
N11 C34 S6 123.6(2) . . ?
N12 C34 S6 119.4(2) . . ?
O11 C35 O12 125.5(3) . . ?
O11 C35 N12 125.1(3) . . ?
O12 C35 N12 109.4(3) . . ?
O14 C38 O13 125.2(3) . . ?
O14 C38 N13 126.5(3) . . ?
O13 C38 N13 108.3(3) . . ?
N14 C39 N13 114.5(3) . . ?
N14 C39 S7 127.0(2) . . ?
N13 C39 S7 118.5(2) . . ?
C45 C40 C41 119.8(3) . . ?
C45 C40 N14 118.7(3) . . ?
C41 C40 N14 121.4(3) . . ?
C42 C41 C40 120.1(3) . . ?
C43 C42 C41 119.7(3) . . ?
C42 C43 C44 120.7(3) . . ?
C43 C44 C45 119.5(3) . . ?
C40 C45 C44 120.1(3) . . ?
C40 C45 N15 120.8(3) . . ?
C44 C45 N15 119.0(3) . . ?
N15 C46 N16 118.2(3) . . ?
N15 C46 S8 122.8(2) . . ?
N16 C46 S8 119.1(2) . . ?
O16 C47 O15 125.5(3) . . ?
O16 C47 N16 124.9(3) . . ?
O15 C47 N16 109.6(3) . . ?
C54 C49 C50 109.0(3) . . ?
C51 C50 C49 111.6(3) . . ?
C50 C51 C52 111.2(3) . . ?
C51 C52 C53 111.0(3) . . ?
C54 C53 C52 109.7(3) . . ?
O17 C54 C49 123.4(3) . . ?
O17 C54 C53 121.8(3) . . ?
C49 C54 C53 114.7(3) . . ?
O18 C55 C60 121.8(3) . . ?
O18 C55 C56 122.6(3) . . ?
C60 C55 C56 115.6(3) . . ?
C55 C56 C57 112.0(3) . . ?
C58 C57 C56 111.5(3) . . ?
C57 C58 C59 110.6(3) . . ?
C58 C59 C60 110.3(3) . . ?
C55 C60 C59 112.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 O2 3.6(4) . . . . ?
C1 O1 C2 N1 -176.2(2) . . . . ?
C3 N1 C2 O2 -0.5(5) . . . . ?
C3 N1 C2 O1 179.3(3) . . . . ?
C4 N2 C3 N1 179.4(3) . . . . ?
C4 N2 C3 S1 0.1(4) . . . . ?
C2 N1 C3 N2 0.9(4) . . . . ?
C2 N1 C3 S1 -179.8(2) . . . . ?
C3 N2 C4 C5 -106.1(3) . . . . ?
C3 N2 C4 C9 78.7(4) . . . . ?
C9 C4 C5 C6 -0.4(4) . . . . ?
N2 C4 C5 C6 -175.6(3) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C7 C8 C9 C4 -2.6(4) . . . . ?
C7 C8 C9 N3 177.8(3) . . . . ?
C5 C4 C9 C8 2.2(4) . . . . ?
N2 C4 C9 C8 177.3(3) . . . . ?
C5 C4 C9 N3 -178.2(3) . . . . ?
N2 C4 C9 N3 -3.1(4) . . . . ?
C10 N3 C9 C8 -54.0(4) . . . . ?
C10 N3 C9 C4 126.4(3) . . . . ?
C9 N3 C10 N4 -175.1(3) . . . . ?
C9 N3 C10 S2 4.6(4) . . . . ?
C11 N4 C10 N3 8.4(4) . . . . ?
C11 N4 C10 S2 -171.3(2) . . . . ?
C12 O4 C11 O3 -3.4(4) . . . . ?
C12 O4 C11 N4 178.1(3) . . . . ?
C10 N4 C11 O3 -6.0(5) . . . . ?
C10 N4 C11 O4 172.5(3) . . . . ?
C13 O5 C14 O6 -2.0(4) . . . . ?
C13 O5 C14 N5 177.2(2) . . . . ?
C15 N5 C14 O6 0.4(5) . . . . ?
C15 N5 C14 O5 -178.8(3) . . . . ?
C16 N6 C15 N5 176.9(3) . . . . ?
C16 N6 C15 S3 -2.2(4) . . . . ?
C14 N5 C15 N6 -9.7(4) . . . . ?
C14 N5 C15 S3 169.5(2) . . . . ?
C15 N6 C16 C21 -122.5(3) . . . . ?
C15 N6 C16 C17 58.3(4) . . . . ?
C21 C16 C17 C18 2.3(5) . . . . ?
N6 C16 C17 C18 -178.5(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 -1.4(5) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C17 C16 C21 C20 -2.6(5) . . . . ?
N6 C16 C21 C20 178.1(3) . . . . ?
C17 C16 C21 N7 179.7(3) . . . . ?
N6 C16 C21 N7 0.5(4) . . . . ?
C19 C20 C21 C16 1.0(5) . . . . ?
C19 C20 C21 N7 178.7(3) . . . . ?
C22 N7 C21 C16 -75.6(4) . . . . ?
C22 N7 C21 C20 106.7(3) . . . . ?
C21 N7 C22 N8 -175.8(3) . . . . ?
C21 N7 C22 S4 5.6(4) . . . . ?
C23 N8 C22 N7 -1.3(4) . . . . ?
C23 N8 C22 S4 177.4(2) . . . . ?
C24 O7 C23 O8 -4.9(4) . . . . ?
C24 O7 C23 N8 174.4(2) . . . . ?
C22 N8 C23 O8 4.7(5) . . . . ?
C22 N8 C23 O7 -174.7(3) . . . . ?
C25 O9 C26 O10 -5.9(4) . . . . ?
C25 O9 C26 N9 174.8(2) . . . . ?
C27 N9 C26 O10 0.9(5) . . . . ?
C27 N9 C26 O9 -179.8(3) . . . . ?
C28 N10 C27 N9 -179.6(3) . . . . ?
C28 N10 C27 S5 -0.3(4) . . . . ?
C26 N9 C27 N10 1.9(4) . . . . ?
C26 N9 C27 S5 -177.5(2) . . . . ?
C27 N10 C28 C29 -59.8(4) . . . . ?
C27 N10 C28 C33 120.5(3) . . . . ?
C33 C28 C29 C30 -3.1(4) . . . . ?
N10 C28 C29 C30 177.1(3) . . . . ?
C28 C29 C30 C31 1.7(4) . . . . ?
C29 C30 C31 C32 0.5(4) . . . . ?
C30 C31 C32 C33 -1.3(4) . . . . ?
C31 C32 C33 C28 -0.2(4) . . . . ?
C31 C32 C33 N11 -176.8(3) . . . . ?
C29 C28 C33 C32 2.4(4) . . . . ?
N10 C28 C33 C32 -177.9(3) . . . . ?
C29 C28 C33 N11 179.0(3) . . . . ?
N10 C28 C33 N11 -1.3(4) . . . . ?
C34 N11 C33 C32 -107.8(3) . . . . ?
C34 N11 C33 C28 75.6(4) . . . . ?
C33 N11 C34 N12 176.0(3) . . . . ?
C33 N11 C34 S6 -3.6(4) . . . . ?
C35 N12 C34 N11 -5.6(4) . . . . ?
C35 N12 C34 S6 174.1(2) . . . . ?
C36 O12 C35 O11 -0.7(4) . . . . ?
C36 O12 C35 N12 179.5(2) . . . . ?
C34 N12 C35 O11 5.3(5) . . . . ?
C34 N12 C35 O12 -174.9(3) . . . . ?
C37 O13 C38 O14 -8.5(5) . . . . ?
C37 O13 C38 N13 172.4(3) . . . . ?
C39 N13 C38 O14 4.6(5) . . . . ?
C39 N13 C38 O13 -176.3(3) . . . . ?
C40 N14 C39 N13 178.9(3) . . . . ?
C40 N14 C39 S7 -1.9(5) . . . . ?
C38 N13 C39 N14 2.3(4) . . . . ?
C38 N13 C39 S7 -177.0(2) . . . . ?
C39 N14 C40 C45 132.5(3) . . . . ?
C39 N14 C40 C41 -50.8(4) . . . . ?
C45 C40 C41 C42 -1.3(5) . . . . ?
N14 C40 C41 C42 -178.1(3) . . . . ?
C40 C41 C42 C43 0.5(5) . . . . ?
C41 C42 C43 C44 0.4(5) . . . . ?
C42 C43 C44 C45 -0.5(5) . . . . ?
C41 C40 C45 C44 1.3(5) . . . . ?
N14 C40 C45 C44 178.1(3) . . . . ?
C41 C40 C45 N15 -179.5(3) . . . . ?
N14 C40 C45 N15 -2.7(4) . . . . ?
C43 C44 C45 C40 -0.4(5) . . . . ?
C43 C44 C45 N15 -179.6(3) . . . . ?
C46 N15 C45 C40 89.1(4) . . . . ?
C46 N15 C45 C44 -91.7(4) . . . . ?
C45 N15 C46 N16 172.9(3) . . . . ?
C45 N15 C46 S8 -8.2(4) . . . . ?
C47 N16 C46 N15 4.5(4) . . . . ?
C47 N16 C46 S8 -174.5(2) . . . . ?
C48 O15 C47 O16 2.1(4) . . . . ?
C48 O15 C47 N16 -177.0(2) . . . . ?
C46 N16 C47 O16 2.0(5) . . . . ?
C46 N16 C47 O15 -178.9(3) . . . . ?
C54 C49 C50 C51 55.8(3) . . . . ?
C49 C50 C51 C52 -57.0(4) . . . . ?
C50 C51 C52 C53 55.5(4) . . . . ?
C51 C52 C53 C54 -53.3(3) . . . . ?
C50 C49 C54 O17 120.9(3) . . . . ?
C50 C49 C54 C53 -56.3(3) . . . . ?
C52 C53 C54 O17 -121.7(3) . . . . ?
C52 C53 C54 C49 55.6(4) . . . . ?
O18 C55 C56 C57 133.4(3) . . . . ?
C60 C55 C56 C57 -47.4(4) . . . . ?
C55 C56 C57 C58 52.1(4) . . . . ?
C56 C57 C58 C59 -58.4(4) . . . . ?
C57 C58 C59 C60 57.7(4) . . . . ?
O18 C55 C60 C59 -133.1(3) . . . . ?
C56 C55 C60 C59 47.7(4) . . . . ?
C58 C59 C60 C55 -52.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.893(17) 1.96(2) 2.675(3) 136(2) .
N3 H3 O3 0.900(17) 1.89(2) 2.644(3) 139(2) .
N3 H3 S1 0.900(17) 2.89(2) 3.531(3) 129(2) .
N6 H6 O6 0.886(17) 1.99(2) 2.681(3) 134(3) .
N6 H6 S4 0.886(17) 2.73(2) 3.388(3) 132(2) .
N7 H7 O8 0.895(17) 1.92(2) 2.673(3) 141(2) .
N10 H10 O10 0.896(17) 1.98(2) 2.672(3) 133(2) .
N10 H10 S6 0.896(17) 2.76(2) 3.389(3) 128(2) .
N11 H11 O11 0.872(17) 1.95(2) 2.674(3) 140(2) .
N11 H11 O16 0.872(17) 2.40(2) 3.061(3) 133(2) .
N14 H14 O14 0.907(17) 1.94(2) 2.664(3) 136(2) .
N15 H15 O16 0.885(17) 1.97(2) 2.697(3) 138(2) .
N15 H15 O11 0.885(17) 2.32(2) 2.984(3) 132(2) .
N1 H1 S8 0.899(17) 2.411(18) 3.306(3) 174(2) 1_556
N2 H2 O8 0.893(17) 2.23(2) 2.921(3) 134(2) 2_666
N4 H4 O18 0.900(17) 2.092(18) 2.980(3) 168(3) 2_666
N5 H5 O5 0.905(17) 2.422(19) 3.302(3) 164(2) 2_666
N7 H7 O2 0.895(17) 2.32(2) 2.976(3) 130(2) 2_666
N8 H8 S6 0.879(17) 2.513(19) 3.364(3) 163(3) 2_766
N9 H9 O17 0.904(17) 2.095(18) 2.994(3) 173(3) 2_666
N12 H12 S4 0.890(17) 2.427(18) 3.316(3) 176(2) 2_766
N13 H13 O18 0.877(17) 2.40(2) 3.099(3) 138(2) 2_765
N13 H13 O13 0.877(17) 2.73(3) 3.322(4) 126(2) 2_765
N16 H16 S1 0.891(17) 2.631(18) 3.515(3) 171(3) 1_554

_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_theta_full        57.68
_diffrn_measured_fraction_theta_full 0.896
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.058

data_TM_DMSO
_database_code_depnum_ccdc_archive 'CCDC 724469'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, dimethylsulfoxide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C2 H6 O1 S1'
_chemical_formula_sum            'C14 H20 N4 O5 S3'
_chemical_formula_weight         420.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   26.524(15)
_cell_length_b                   10.321(5)
_cell_length_c                   17.428(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.66(3)
_cell_angle_gamma                90.00
_cell_volume                     4755(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    3.094
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5765
_exptl_absorpt_correction_T_max  0.5765
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12637
_diffrn_reflns_av_R_equivalents  0.1367
_diffrn_reflns_av_sigmaI/netI    0.1384
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         57.88
_reflns_number_total             3184
_reflns_number_gt                1920
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
Residual electron density in the DMSO solvate that could be assigned to
severely disordered DMSO molecules was removed with the program SQUEEZE.
(P. van der Sluis and A.L. Spek, Acta Cryst., 1990, A46, 194-201.)
;

_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)+(0.1267P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3184
_refine_ls_number_parameters     239
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0899
_refine_ls_wR_factor_ref         0.2250
_refine_ls_wR_factor_gt          0.2145
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42836(6) 0.49026(18) 0.44188(10) 0.0408(6) Uani 1 1 d . . .
S2 S 0.31364(7) 0.08525(16) 0.27599(9) 0.0333(6) Uani 1 1 d . . .
O1 O 0.53072(15) 0.2071(4) 0.3259(2) 0.0248(11) Uani 1 1 d . . .
O2 O 0.58033(15) 0.2430(4) 0.4359(2) 0.0296(12) Uani 1 1 d . . .
O3 O 0.32638(19) 0.3013(4) 0.5049(2) 0.0422(14) Uani 1 1 d . . .
O4 O 0.30598(16) 0.1062(4) 0.5509(2) 0.0284(11) Uani 1 1 d . . .
N1 N 0.50600(19) 0.3370(5) 0.4236(3) 0.0301(14) Uani 1 1 d D . .
H1 H 0.5147 0.3604 0.4715 0.036 Uiso 1 1 calc RD . .
N2 N 0.44549(18) 0.3487(5) 0.3195(3) 0.0237(13) Uani 1 1 d D . .
H2 H 0.4633 0.2877 0.2991 0.028 Uiso 1 1 calc RD . .
N3 N 0.34437(19) 0.2954(5) 0.3555(3) 0.0235(13) Uani 1 1 d D . .
H3 H 0.3518 0.3322 0.4005 0.028 Uiso 1 1 calc RD . .
N4 N 0.31652(18) 0.1216(5) 0.4261(3) 0.0235(13) Uani 1 1 d D . .
H4 H 0.3096 0.0382 0.4271 0.028 Uiso 1 1 calc RD . .
C1 C 0.6200(3) 0.1623(7) 0.4047(4) 0.042(2) Uani 1 1 d . . .
H1A H 0.6067 0.0751 0.3937 0.063 Uiso 1 1 calc R . .
H1B H 0.6493 0.1570 0.4425 0.063 Uiso 1 1 calc R . .
H1C H 0.6302 0.2014 0.3571 0.063 Uiso 1 1 calc R . .
C2 C 0.5387(2) 0.2552(6) 0.3897(4) 0.0244(16) Uani 1 1 d . . .
C3 C 0.4602(2) 0.3870(6) 0.3899(3) 0.0252(16) Uani 1 1 d . . .
C4 C 0.4032(2) 0.3982(6) 0.2744(3) 0.0198(15) Uani 1 1 d . . .
C5 C 0.4116(2) 0.4743(6) 0.2104(3) 0.0252(16) Uani 1 1 d . . .
H5 H 0.4450 0.5003 0.2017 0.030 Uiso 1 1 calc R . .
C6 C 0.3717(2) 0.5119(6) 0.1595(4) 0.0261(16) Uani 1 1 d . . .
H6 H 0.3780 0.5616 0.1155 0.031 Uiso 1 1 calc R . .
C7 C 0.3227(3) 0.4782(6) 0.1720(3) 0.0290(17) Uani 1 1 d . . .
H7 H 0.2955 0.5027 0.1362 0.035 Uiso 1 1 calc R . .
C8 C 0.3139(2) 0.4080(5) 0.2376(3) 0.0214(15) Uani 1 1 d . . .
H8 H 0.2801 0.3880 0.2478 0.026 Uiso 1 1 calc R . .
C9 C 0.3533(2) 0.3671(5) 0.2880(3) 0.0175(15) Uani 1 1 d . . .
C10 C 0.3251(2) 0.1736(6) 0.3541(3) 0.0252(16) Uani 1 1 d . . .
C11 C 0.3176(2) 0.1851(8) 0.4950(4) 0.0328(18) Uani 1 1 d . . .
C12 C 0.3052(3) 0.1617(7) 0.6257(3) 0.0375(19) Uani 1 1 d . . .
H12A H 0.3391 0.1927 0.6432 0.056 Uiso 1 1 calc R . .
H12B H 0.2945 0.0960 0.6617 0.056 Uiso 1 1 calc R . .
H12C H 0.2814 0.2344 0.6238 0.056 Uiso 1 1 calc R . .
S3 S 0.21162(7) 0.25734(16) 0.12081(10) 0.0385(6) Uani 1 1 d . . .
O6 O 0.20235(17) 0.3603(4) 0.0607(2) 0.0362(12) Uani 1 1 d . . .
C13 C 0.1543(3) 0.2388(7) 0.1640(4) 0.050(2) Uani 1 1 d . . .
H13A H 0.1479 0.3166 0.1939 0.075 Uiso 1 1 calc R . .
H13B H 0.1566 0.1633 0.1982 0.075 Uiso 1 1 calc R . .
H13C H 0.1266 0.2262 0.1240 0.075 Uiso 1 1 calc R . .
C14 C 0.2096(3) 0.1073(6) 0.0677(4) 0.054(2) Uani 1 1 d . . .
H14A H 0.1771 0.1001 0.0370 0.082 Uiso 1 1 calc R . .
H14B H 0.2134 0.0344 0.1038 0.082 Uiso 1 1 calc R . .
H14C H 0.2371 0.1058 0.0335 0.082 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
S1 C3 1.672(6) . ?
S2 C10 1.647(6) . ?
O1 C2 1.221(7) . ?
O2 C2 1.319(7) . ?
O2 C1 1.479(7) . ?
O3 C11 1.232(8) . ?
O4 C11 1.325(7) . ?
O4 C12 1.426(7) . ?
N1 C2 1.378(8) . ?
N1 C3 1.404(8) . ?
N1 H1 0.8800 . ?
N2 C3 1.318(7) . ?
N2 C4 1.411(7) . ?
N2 H2 0.8800 . ?
N3 C10 1.356(8) . ?
N3 C9 1.425(7) . ?
N3 H3 0.8800 . ?
N4 C11 1.366(8) . ?
N4 C10 1.400(7) . ?
N4 H4 0.8800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.397(8) . ?
C4 C9 1.402(8) . ?
C5 C6 1.381(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(8) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S3 O6 1.498(4) . ?
S3 C13 1.760(7) . ?
S3 C14 1.803(7) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C2 O2 C1 114.4(5) . . ?
C11 O4 C12 116.6(5) . . ?
C2 N1 C3 126.8(5) . . ?
C2 N1 H1 116.6 . . ?
C3 N1 H1 116.6 . . ?
C3 N2 C4 124.9(5) . . ?
C3 N2 H2 117.6 . . ?
C4 N2 H2 117.6 . . ?
C10 N3 C9 123.7(5) . . ?
C10 N3 H3 118.2 . . ?
C9 N3 H3 118.2 . . ?
C11 N4 C10 127.6(5) . . ?
C11 N4 H4 116.2 . . ?
C10 N4 H4 116.2 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 126.3(6) . . ?
O1 C2 N1 124.9(6) . . ?
O2 C2 N1 108.8(6) . . ?
N2 C3 N1 117.4(5) . . ?
N2 C3 S1 124.8(5) . . ?
N1 C3 S1 117.8(4) . . ?
C5 C4 C9 118.6(5) . . ?
C5 C4 N2 118.5(5) . . ?
C9 C4 N2 122.8(5) . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.8(6) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.1(6) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 120.9(6) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C4 120.1(5) . . ?
C8 C9 N3 121.1(5) . . ?
C4 C9 N3 118.8(5) . . ?
N3 C10 N4 115.4(5) . . ?
N3 C10 S2 124.9(5) . . ?
N4 C10 S2 119.7(5) . . ?
O3 C11 O4 123.3(6) . . ?
O3 C11 N4 125.4(6) . . ?
O4 C11 N4 111.2(6) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 S3 C13 106.1(3) . . ?
O6 S3 C14 104.7(3) . . ?
C13 S3 C14 97.8(3) . . ?
S3 C13 H13A 109.5 . . ?
S3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S3 C14 H14A 109.5 . . ?
S3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 0.0(9) . . . . ?
C1 O2 C2 N1 -177.1(5) . . . . ?
C3 N1 C2 O1 -5.1(10) . . . . ?
C3 N1 C2 O2 172.1(6) . . . . ?
C4 N2 C3 N1 -173.7(5) . . . . ?
C4 N2 C3 S1 6.5(9) . . . . ?
C2 N1 C3 N2 2.9(9) . . . . ?
C2 N1 C3 S1 -177.3(5) . . . . ?
C3 N2 C4 C5 110.1(7) . . . . ?
C3 N2 C4 C9 -74.4(8) . . . . ?
C9 C4 C5 C6 -3.4(8) . . . . ?
N2 C4 C5 C6 172.3(5) . . . . ?
C4 C5 C6 C7 1.7(9) . . . . ?
C5 C6 C7 C8 1.4(9) . . . . ?
C6 C7 C8 C9 -2.9(9) . . . . ?
C7 C8 C9 C4 1.2(8) . . . . ?
C7 C8 C9 N3 179.8(5) . . . . ?
C5 C4 C9 C8 1.9(8) . . . . ?
N2 C4 C9 C8 -173.6(5) . . . . ?
C5 C4 C9 N3 -176.7(5) . . . . ?
N2 C4 C9 N3 7.8(8) . . . . ?
C10 N3 C9 C8 66.9(8) . . . . ?
C10 N3 C9 C4 -114.5(6) . . . . ?
C9 N3 C10 N4 -176.7(5) . . . . ?
C9 N3 C10 S2 5.4(8) . . . . ?
C11 N4 C10 N3 11.3(9) . . . . ?
C11 N4 C10 S2 -170.8(5) . . . . ?
C12 O4 C11 O3 -1.4(9) . . . . ?
C12 O4 C11 N4 -179.3(5) . . . . ?
C10 N4 C11 O3 0.1(10) . . . . ?
C10 N4 C11 O4 177.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.88 1.99 2.687(6) 134.9 .
N3 H3 O3 0.88 2.02 2.686(6) 132.1 .
N3 H3 S1 0.88 2.66 3.276(5) 128.1 .
N1 H1 S1 0.88 2.56 3.322(5) 145.0 5_666
N2 H2 O1 0.88 2.35 3.036(6) 135.0 2_655
N4 H4 O6 0.88 1.88 2.756(6) 174.4 4_545

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        57.88
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.120

data_TM_chloroform
_database_code_depnum_ccdc_archive 'CCDC 724470'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, chloroform'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C1 H1 Cl3'
_chemical_formula_sum            'C13 H15 Cl3 N4 O4 S2'
_chemical_formula_weight         461.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   10.626(2)
_cell_length_b                   14.706(3)
_cell_length_c                   14.739(3)
_cell_angle_alpha                63.51(3)
_cell_angle_beta                 77.34(3)
_cell_angle_gamma                74.82(3)
_cell_volume                     1975.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    6.428
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2964
_exptl_absorpt_correction_T_max  0.4456
_exptl_absorpt_process_details   
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD Apex II detector'
_diffrn_measurement_method       'psi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10630
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         67.04
_reflns_number_total             6828
_reflns_number_gt                5393
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS, 2004)'
_computing_cell_refinement       Denzo
_computing_data_reduction        Denzo
_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 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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0649P)²+3.3649P] 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         6828
_refine_ls_number_parameters     497
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.93464(9) 0.65758(7) -0.11013(8) 0.0402(3) Uani 1 1 d . . .
S2 S 0.27149(8) 0.87650(8) -0.01131(7) 0.0316(2) Uani 1 1 d . . .
S3 S 0.52375(9) 0.83994(7) 0.52833(7) 0.0342(2) Uani 1 1 d . . .
S4 S 1.07701(8) 0.74419(7) 0.28580(6) 0.0297(2) Uani 1 1 d . . .
O1 O 0.5919(3) 0.5806(2) 0.1424(2) 0.0384(6) Uani 1 1 d . . .
O2 O 0.7380(3) 0.4347(2) 0.2113(2) 0.0404(7) Uani 1 1 d . . .
O3 O 0.5687(2) 0.7561(2) 0.21950(18) 0.0304(5) Uani 1 1 d . . .
O4 O 0.3923(2) 0.6976(2) 0.32686(18) 0.0328(6) Uani 1 1 d . . .
O5 O 0.8340(3) 0.9838(2) 0.2691(2) 0.0414(7) Uani 1 1 d . . .
O6 O 0.7278(3) 1.12662(19) 0.2941(2) 0.0392(7) Uani 1 1 d . . .
O7 O 0.7875(2) 0.8409(2) 0.05628(18) 0.0318(6) Uani 1 1 d . . .
O8 O 0.9482(2) 0.92411(19) -0.05093(17) 0.0280(5) Uani 1 1 d . . .
N1 N 0.7975(3) 0.5498(2) 0.0587(2) 0.0311(7) Uani 1 1 d D . .
H1N H 0.871(3) 0.501(3) 0.069(3) 0.037 Uiso 1 1 d D . .
N2 N 0.6812(3) 0.7052(2) -0.0430(2) 0.0276(6) Uani 1 1 d D . .
H2N H 0.616(3) 0.683(3) 0.007(2) 0.033 Uiso 1 1 d D . .
N3 N 0.5189(3) 0.8456(2) 0.0216(2) 0.0232(6) Uani 1 1 d D . .
H3N H 0.577(3) 0.821(3) 0.067(2) 0.028 Uiso 1 1 d D . .
N4 N 0.3665(3) 0.7925(2) 0.1651(2) 0.0261(6) Uani 1 1 d D . .
H4N H 0.282(2) 0.787(3) 0.190(3) 0.031 Uiso 1 1 d D . .
N5 N 0.6534(3) 0.9815(2) 0.3888(2) 0.0291(7) Uani 1 1 d D . .
H5N H 0.596(3) 1.025(3) 0.413(3) 0.035 Uiso 1 1 d D . .
N6 N 0.7394(3) 0.8177(2) 0.3979(2) 0.0277(6) Uani 1 1 d D . .
H6N H 0.794(3) 0.851(3) 0.344(2) 0.033 Uiso 1 1 d D . .
N7 N 0.8426(3) 0.7430(2) 0.2509(2) 0.0222(6) Uani 1 1 d D . .
H7N H 0.782(3) 0.764(3) 0.209(2) 0.027 Uiso 1 1 d D . .
N8 N 0.9744(3) 0.8396(2) 0.1118(2) 0.0258(6) Uani 1 1 d D . .
H8N H 1.055(2) 0.856(3) 0.086(3) 0.031 Uiso 1 1 d D . .
C1 C 0.6416(5) 0.4001(4) 0.2996(3) 0.0574(13) Uani 1 1 d . . .
H1A H 0.6130 0.4520 0.3281 0.086 Uiso 1 1 calc R . .
H1B H 0.6808 0.3343 0.3511 0.086 Uiso 1 1 calc R . .
H1C H 0.5658 0.3907 0.2791 0.086 Uiso 1 1 calc R . .
C2 C 0.6990(4) 0.5264(3) 0.1381(3) 0.0301(8) Uani 1 1 d . . .
C3 C 0.7965(4) 0.6403(3) -0.0305(3) 0.0285(8) Uani 1 1 d . . .
C4 C 0.6494(3) 0.8071(3) -0.1185(3) 0.0251(7) Uani 1 1 d . . .
C5 C 0.6926(4) 0.8374(3) -0.2221(3) 0.0318(8) Uani 1 1 d . . .
H5 H 0.7485 0.7889 -0.2463 0.038 Uiso 1 1 calc R . .
C6 C 0.6540(4) 0.9383(3) -0.2894(3) 0.0352(9) Uani 1 1 d . . .
H6 H 0.6839 0.9590 -0.3601 0.042 Uiso 1 1 calc R . .
C7 C 0.5719(4) 1.0102(3) -0.2554(3) 0.0320(8) Uani 1 1 d . . .
H7 H 0.5476 1.0799 -0.3024 0.038 Uiso 1 1 calc R . .
C8 C 0.5258(3) 0.9802(3) -0.1531(3) 0.0289(8) Uani 1 1 d . . .
H8 H 0.4681 1.0287 -0.1296 0.035 Uiso 1 1 calc R . .
C9 C 0.5639(3) 0.8790(3) -0.0846(2) 0.0241(7) Uani 1 1 d . . .
C10 C 0.3943(3) 0.8375(3) 0.0597(3) 0.0238(7) Uani 1 1 d . . .
C11 C 0.4551(3) 0.7492(3) 0.2360(3) 0.0253(7) Uani 1 1 d . . .
C12 C 0.4692(4) 0.6506(3) 0.4111(3) 0.0358(9) Uani 1 1 d . . .
H12A H 0.5538 0.6126 0.3926 0.054 Uiso 1 1 calc R . .
H12B H 0.4220 0.6026 0.4708 0.054 Uiso 1 1 calc R . .
H12C H 0.4840 0.7044 0.4274 0.054 Uiso 1 1 calc R . .
C13 C 0.8257(5) 1.1823(3) 0.2199(4) 0.0486(12) Uani 1 1 d . . .
H13A H 0.9113 1.1531 0.2459 0.073 Uiso 1 1 calc R . .
H13B H 0.8012 1.2555 0.2080 0.073 Uiso 1 1 calc R . .
H13C H 0.8308 1.1761 0.1557 0.073 Uiso 1 1 calc R . .
C14 C 0.7470(4) 1.0276(3) 0.3122(3) 0.0318(8) Uani 1 1 d . . .
C15 C 0.6456(3) 0.8780(3) 0.4355(3) 0.0275(7) Uani 1 1 d . . .
C16 C 0.7626(3) 0.7089(3) 0.4303(3) 0.0259(7) Uani 1 1 d . . .
C17 C 0.7419(4) 0.6391(3) 0.5306(3) 0.0310(8) Uani 1 1 d . . .
H17 H 0.7058 0.6635 0.5824 0.037 Uiso 1 1 calc R . .
C18 C 0.7734(4) 0.5342(3) 0.5559(3) 0.0379(9) Uani 1 1 d . . .
H18 H 0.7592 0.4867 0.6250 0.046 Uiso 1 1 calc R . .
C19 C 0.8257(4) 0.4980(3) 0.4810(3) 0.0396(9) Uani 1 1 d . . .
H19 H 0.8457 0.4258 0.4985 0.048 Uiso 1 1 calc R . .
C20 C 0.8486(4) 0.5668(3) 0.3811(3) 0.0315(8) Uani 1 1 d . . .
H20 H 0.8856 0.5419 0.3298 0.038 Uiso 1 1 calc R . .
C21 C 0.8181(3) 0.6720(3) 0.3551(2) 0.0237(7) Uani 1 1 d . . .
C22 C 0.9566(3) 0.7765(2) 0.2133(2) 0.0222(7) Uani 1 1 d . . .
C23 C 0.8927(3) 0.8664(3) 0.0391(2) 0.0239(7) Uani 1 1 d . . .
C24 C 0.8739(4) 0.9600(3) -0.1359(3) 0.0308(8) Uani 1 1 d . . .
H24A H 0.8665 0.9006 -0.1469 0.046 Uiso 1 1 calc R . .
H24B H 0.9189 1.0074 -0.1976 0.046 Uiso 1 1 calc R . .
H24C H 0.7859 0.9961 -0.1208 0.046 Uiso 1 1 calc R . .
C100 C 1.0276(5) 0.8000(4) 0.5096(4) 0.0518(12) Uani 1 1 d . . .
H100 H 1.0076 0.7836 0.4559 0.062 Uiso 1 1 calc R . .
Cl1 Cl 1.01536(16) 0.69349(12) 0.62759(11) 0.0754(4) Uani 1 1 d . . .
Cl2 Cl 0.91295(14) 0.90669(13) 0.51616(13) 0.0796(5) Uani 1 1 d . . .
Cl3 Cl 1.18657(13) 0.82687(12) 0.47752(11) 0.0735(4) Uani 1 1 d . . .
C200 C 0.7207(6) 0.4215(5) 0.8933(5) 0.0691(15) Uani 1 1 d . . .
H200 H 0.7040 0.3798 0.8605 0.083 Uiso 1 1 calc R . .
Cl4 Cl 0.88672(18) 0.39004(16) 0.9086(2) 0.1169(8) Uani 1 1 d . . .
Cl5 Cl 0.67381(18) 0.55446(13) 0.81453(11) 0.0836(5) Uani 1 1 d . . .
Cl6 Cl 0.62660(17) 0.39097(11) 1.01243(11) 0.0779(4) 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
S1 C3 1.664(4) . ?
S2 C10 1.673(3) . ?
S3 C15 1.668(4) . ?
S4 C22 1.684(3) . ?
O1 C2 1.214(4) . ?
O2 C2 1.326(4) . ?
O2 C1 1.449(5) . ?
O3 C11 1.201(4) . ?
O4 C11 1.335(4) . ?
O4 C12 1.439(4) . ?
O5 C14 1.211(4) . ?
O6 C14 1.325(4) . ?
O6 C13 1.449(5) . ?
O7 C23 1.210(4) . ?
O8 C23 1.320(4) . ?
O8 C24 1.449(4) . ?
N1 C2 1.370(5) . ?
N1 C3 1.393(5) . ?
N1 H1N 0.897(19) . ?
N2 C3 1.332(5) . ?
N2 C4 1.418(4) . ?
N2 H2N 0.898(19) . ?
N3 C10 1.335(4) . ?
N3 C9 1.425(4) . ?
N3 H3N 0.896(19) . ?
N4 C11 1.380(4) . ?
N4 C10 1.387(4) . ?
N4 H4N 0.900(19) . ?
N5 C14 1.379(5) . ?
N5 C15 1.379(5) . ?
N5 H5N 0.903(19) . ?
N6 C15 1.349(5) . ?
N6 C16 1.419(4) . ?
N6 H6N 0.903(19) . ?
N7 C22 1.339(4) . ?
N7 C21 1.433(4) . ?
N7 H7N 0.885(19) . ?
N8 C22 1.365(4) . ?
N8 C23 1.382(4) . ?
N8 H8N 0.904(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.391(5) . ?
C4 C9 1.400(5) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(5) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 C17 1.381(5) . ?
C16 C21 1.398(5) . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C100 Cl2 1.742(5) . ?
C100 Cl3 1.751(5) . ?
C100 Cl1 1.753(5) . ?
C100 H100 1.0000 . ?
C200 Cl4 1.741(6) . ?
C200 Cl6 1.746(6) . ?
C200 Cl5 1.771(6) . ?
C200 H200 1.0000 . ?

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
C2 O2 C1 115.3(3) . . ?
C11 O4 C12 115.5(3) . . ?
C14 O6 C13 114.9(3) . . ?
C23 O8 C24 115.8(3) . . ?
C2 N1 C3 127.2(3) . . ?
C2 N1 H1N 114(3) . . ?
C3 N1 H1N 119(3) . . ?
C3 N2 C4 129.4(3) . . ?
C3 N2 H2N 115(3) . . ?
C4 N2 H2N 115(3) . . ?
C10 N3 C9 123.0(3) . . ?
C10 N3 H3N 117(2) . . ?
C9 N3 H3N 120(2) . . ?
C11 N4 C10 127.2(3) . . ?
C11 N4 H4N 116(3) . . ?
C10 N4 H4N 116(3) . . ?
C14 N5 C15 127.5(3) . . ?
C14 N5 H5N 114(3) . . ?
C15 N5 H5N 119(3) . . ?
C15 N6 C16 129.1(3) . . ?
C15 N6 H6N 116(3) . . ?
C16 N6 H6N 115(3) . . ?
C22 N7 C21 121.8(3) . . ?
C22 N7 H7N 118(3) . . ?
C21 N7 H7N 120(3) . . ?
C22 N8 C23 127.4(3) . . ?
C22 N8 H8N 117(3) . . ?
C23 N8 H8N 114(3) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.3(3) . . ?
O1 C2 N1 125.9(3) . . ?
O2 C2 N1 109.7(3) . . ?
N2 C3 N1 114.8(3) . . ?
N2 C3 S1 126.5(3) . . ?
N1 C3 S1 118.6(3) . . ?
C5 C4 C9 119.3(3) . . ?
C5 C4 N2 124.3(3) . . ?
C9 C4 N2 116.3(3) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.5(3) . . ?
C8 C9 N3 121.2(3) . . ?
C4 C9 N3 118.3(3) . . ?
N3 C10 N4 117.2(3) . . ?
N3 C10 S2 124.3(3) . . ?
N4 C10 S2 118.6(3) . . ?
O3 C11 O4 125.6(3) . . ?
O3 C11 N4 126.4(3) . . ?
O4 C11 N4 108.0(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 125.4(3) . . ?
O5 C14 N5 125.1(3) . . ?
O6 C14 N5 109.4(3) . . ?
N6 C15 N5 114.5(3) . . ?
N6 C15 S3 126.7(3) . . ?
N5 C15 S3 118.8(3) . . ?
C17 C16 C21 119.2(3) . . ?
C17 C16 N6 124.3(3) . . ?
C21 C16 N6 116.3(3) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 N7 119.9(3) . . ?
C16 C21 N7 120.2(3) . . ?
N7 C22 N8 118.0(3) . . ?
N7 C22 S4 122.7(3) . . ?
N8 C22 S4 119.3(3) . . ?
O7 C23 O8 126.2(3) . . ?
O7 C23 N8 124.9(3) . . ?
O8 C23 N8 108.8(3) . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl2 C100 Cl3 110.5(3) . . ?
Cl2 C100 Cl1 109.2(2) . . ?
Cl3 C100 Cl1 110.4(3) . . ?
Cl2 C100 H100 108.9 . . ?
Cl3 C100 H100 108.9 . . ?
Cl1 C100 H100 108.9 . . ?
Cl4 C200 Cl6 109.7(3) . . ?
Cl4 C200 Cl5 111.3(3) . . ?
Cl6 C200 Cl5 109.7(3) . . ?
Cl4 C200 H200 108.7 . . ?
Cl6 C200 H200 108.7 . . ?
Cl5 C200 H200 108.7 . . ?

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
C1 O2 C2 O1 1.1(6) . . . . ?
C1 O2 C2 N1 -179.2(4) . . . . ?
C3 N1 C2 O1 2.0(6) . . . . ?
C3 N1 C2 O2 -177.6(3) . . . . ?
C4 N2 C3 N1 172.9(3) . . . . ?
C4 N2 C3 S1 -7.4(6) . . . . ?
C2 N1 C3 N2 -7.7(5) . . . . ?
C2 N1 C3 S1 172.6(3) . . . . ?
C3 N2 C4 C5 44.5(6) . . . . ?
C3 N2 C4 C9 -138.4(4) . . . . ?
C9 C4 C5 C6 1.9(5) . . . . ?
N2 C4 C5 C6 178.9(4) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
C5 C6 C7 C8 -1.4(6) . . . . ?
C6 C7 C8 C9 1.4(6) . . . . ?
C7 C8 C9 C4 0.3(5) . . . . ?
C7 C8 C9 N3 179.5(3) . . . . ?
C5 C4 C9 C8 -1.9(5) . . . . ?
N2 C4 C9 C8 -179.2(3) . . . . ?
C5 C4 C9 N3 178.8(3) . . . . ?
N2 C4 C9 N3 1.6(5) . . . . ?
C10 N3 C9 C8 68.8(4) . . . . ?
C10 N3 C9 C4 -112.0(4) . . . . ?
C9 N3 C10 N4 172.4(3) . . . . ?
C9 N3 C10 S2 -6.8(5) . . . . ?
C11 N4 C10 N3 -4.1(5) . . . . ?
C11 N4 C10 S2 175.1(3) . . . . ?
C12 O4 C11 O3 2.4(5) . . . . ?
C12 O4 C11 N4 -177.6(3) . . . . ?
C10 N4 C11 O3 11.5(6) . . . . ?
C10 N4 C11 O4 -168.4(3) . . . . ?
C13 O6 C14 O5 -3.5(6) . . . . ?
C13 O6 C14 N5 175.7(4) . . . . ?
C15 N5 C14 O5 4.8(7) . . . . ?
C15 N5 C14 O6 -174.4(3) . . . . ?
C16 N6 C15 N5 177.5(3) . . . . ?
C16 N6 C15 S3 -3.8(6) . . . . ?
C14 N5 C15 N6 -2.1(5) . . . . ?
C14 N5 C15 S3 179.1(3) . . . . ?
C15 N6 C16 C17 -34.5(6) . . . . ?
C15 N6 C16 C21 149.9(4) . . . . ?
C21 C16 C17 C18 -1.2(6) . . . . ?
N6 C16 C17 C18 -176.7(4) . . . . ?
C16 C17 C18 C19 -0.2(6) . . . . ?
C17 C18 C19 C20 1.2(7) . . . . ?
C18 C19 C20 C21 -0.8(6) . . . . ?
C19 C20 C21 C16 -0.5(6) . . . . ?
C19 C20 C21 N7 179.9(3) . . . . ?
C17 C16 C21 C20 1.5(5) . . . . ?
N6 C16 C21 C20 177.4(3) . . . . ?
C17 C16 C21 N7 -178.9(3) . . . . ?
N6 C16 C21 N7 -3.0(5) . . . . ?
C22 N7 C21 C20 -90.7(4) . . . . ?
C22 N7 C21 C16 89.7(4) . . . . ?
C21 N7 C22 N8 176.5(3) . . . . ?
C21 N7 C22 S4 -3.7(4) . . . . ?
C23 N8 C22 N7 -6.7(5) . . . . ?
C23 N8 C22 S4 173.4(3) . . . . ?
C24 O8 C23 O7 0.4(5) . . . . ?
C24 O8 C23 N8 -179.3(3) . . . . ?
C22 N8 C23 O7 3.8(6) . . . . ?
C22 N8 C23 O8 -176.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N S1 0.897(19) 2.62(2) 3.509(3) 173(4) 2_765
N2 H2N O1 0.898(19) 1.90(3) 2.652(4) 140(4) .
N3 H3N O3 0.896(19) 2.01(3) 2.721(4) 136(3) .
N3 H3N O7 0.896(19) 2.30(3) 2.986(4) 134(3) .
N4 H4N S4 0.900(19) 2.39(2) 3.279(3) 168(4) 1_455
N5 H5N S3 0.903(19) 2.45(2) 3.346(3) 169(4) 2_676
N6 H6N O5 0.903(19) 1.88(3) 2.626(4) 139(3) .
N7 H7N O7 0.885(19) 2.02(3) 2.693(4) 132(3) .
N7 H7N O3 0.885(19) 2.27(3) 2.990(4) 138(3) .
N8 H8N S2 0.904(19) 2.45(2) 3.326(3) 164(3) 1_655

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        67.04
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.084

data_TM_THF
_database_code_depnum_ccdc_archive 'CCDC 724471'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, tetrahydrofuran'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C4 H8 O1'
_chemical_formula_sum            'C16 H22 N4 O5 S2'
_chemical_formula_weight         414.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.5457(19)
_cell_length_b                   14.470(3)
_cell_length_c                   14.592(2)
_cell_angle_alpha                65.317(8)
_cell_angle_beta                 77.658(10)
_cell_angle_gamma                76.287(10)
_cell_volume                     1948.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.792
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7599
_exptl_absorpt_correction_T_max  0.7599
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9286
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         57.27
_reflns_number_total             4514
_reflns_number_gt                3795
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0963P)²+0.4116P] 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     SHELXL
_refine_ls_extinction_coef       0.0101(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4514
_refine_ls_number_parameters     516
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22157(10) 0.47923(8) 0.15205(8) 0.0271(3) Uani 1 1 d . . .
S2 S 0.58528(9) 0.70535(8) 0.27424(8) 0.0246(3) Uani 1 1 d . . .
S3 S 0.67314(10) 1.01347(8) 0.15728(9) 0.0313(3) Uani 1 1 d . . .
S4 S 1.21398(10) 1.06261(8) 0.32326(8) 0.0294(3) Uani 1 1 d . . .
O1 O 0.4951(3) 0.7191(2) 0.0235(2) 0.0258(7) Uani 1 1 d . . .
O2 O 0.4944(3) 0.6988(2) -0.12159(19) 0.0276(7) Uani 1 1 d . . .
O3 O 0.2232(3) 0.9328(2) 0.1430(2) 0.0253(7) Uani 1 1 d . . .
O4 O 0.3745(2) 1.0406(2) 0.07424(19) 0.0229(7) Uani 1 1 d . . .
O5 O 1.0447(3) 0.7762(2) 0.2480(2) 0.0276(7) Uani 1 1 d . . .
O6 O 0.8966(2) 0.6681(2) 0.3099(2) 0.0235(7) Uani 1 1 d . . .
O7 O 0.8894(3) 0.8641(2) 0.4362(2) 0.0299(7) Uani 1 1 d . . .
O8 O 1.0168(3) 0.7698(2) 0.5607(2) 0.0278(7) Uani 1 1 d . . .
O9 O 0.6668(3) 0.4656(2) 0.1228(2) 0.0306(7) Uani 1 1 d . . .
O10 O 0.3083(3) 0.8330(2) 0.5427(2) 0.0298(7) Uani 1 1 d . . .
N1 N 0.3787(3) 0.6051(2) 0.0183(2) 0.0219(8) Uani 1 1 d D . .
H1 H 0.361(4) 0.579(3) -0.022(3) 0.026 Uiso 1 1 d D . .
N2 N 0.3675(3) 0.5916(2) 0.1823(2) 0.0223(8) Uani 1 1 d D . .
H2 H 0.410(3) 0.646(2) 0.148(3) 0.027 Uiso 1 1 d D . .
N3 N 0.3292(3) 0.7400(2) 0.2619(2) 0.0186(8) Uani 1 1 d D . .
H3 H 0.258(3) 0.785(2) 0.238(3) 0.022 Uiso 1 1 d D . .
N4 N 0.4395(3) 0.8808(3) 0.1737(2) 0.0208(8) Uani 1 1 d D . .
H4 H 0.516(3) 0.900(3) 0.169(3) 0.025 Uiso 1 1 d D . .
N5 N 0.8277(3) 0.8336(3) 0.2225(2) 0.0219(8) Uani 1 1 d D . .
H5 H 0.757(3) 0.806(3) 0.232(3) 0.026 Uiso 1 1 d D . .
N6 N 0.9317(3) 0.9752(2) 0.1627(2) 0.0204(8) Uani 1 1 d D . .
H6 H 1.001(3) 0.926(2) 0.180(3) 0.025 Uiso 1 1 d D . .
N7 N 0.9793(3) 1.0344(3) 0.3041(2) 0.0237(8) Uani 1 1 d D . .
H7 H 0.923(3) 0.989(2) 0.335(3) 0.028 Uiso 1 1 d D . .
N8 N 1.0768(3) 0.9158(3) 0.4443(2) 0.0235(8) Uani 1 1 d D . .
H8 H 1.148(3) 0.892(3) 0.478(3) 0.028 Uiso 1 1 d D . .
C1 C 0.5896(4) 0.7694(3) -0.1705(3) 0.0291(10) Uani 1 1 d . . .
H1A H 0.5530 0.8348 -0.1623 0.044 Uiso 1 1 calc R . .
H1B H 0.6089 0.7822 -0.2432 0.044 Uiso 1 1 calc R . .
H1C H 0.6709 0.7387 -0.1391 0.044 Uiso 1 1 calc R . .
C2 C 0.4603(4) 0.6786(3) -0.0230(3) 0.0224(10) Uani 1 1 d . . .
C3 C 0.3274(4) 0.5609(3) 0.1195(3) 0.0201(9) Uani 1 1 d . . .
C4 C 0.3374(4) 0.5599(3) 0.2887(3) 0.0194(9) Uani 1 1 d . . .
C5 C 0.3300(4) 0.4580(3) 0.3550(3) 0.0236(10) Uani 1 1 d . . .
H5A H 0.3407 0.4063 0.3285 0.028 Uiso 1 1 calc R . .
C6 C 0.3073(4) 0.4322(3) 0.4584(3) 0.0241(10) Uani 1 1 d . . .
H6A H 0.3027 0.3626 0.5030 0.029 Uiso 1 1 calc R . .
C7 C 0.2912(4) 0.5063(3) 0.4984(3) 0.0261(10) Uani 1 1 d . . .
H7A H 0.2754 0.4876 0.5700 0.031 Uiso 1 1 calc R . .
C8 C 0.2982(4) 0.6077(3) 0.4339(3) 0.0238(10) Uani 1 1 d . . .
H8A H 0.2865 0.6589 0.4612 0.029 Uiso 1 1 calc R . .
C9 C 0.3225(4) 0.6350(3) 0.3288(3) 0.0200(10) Uani 1 1 d . . .
C10 C 0.4428(4) 0.7780(3) 0.2357(3) 0.0195(9) Uani 1 1 d . . .
C11 C 0.3342(4) 0.9507(3) 0.1314(3) 0.0184(9) Uani 1 1 d . . .
C12 C 0.2748(4) 1.1257(3) 0.0241(3) 0.0271(10) Uani 1 1 d . . .
H12A H 0.2257 1.1032 -0.0104 0.041 Uiso 1 1 calc R . .
H12B H 0.3175 1.1834 -0.0258 0.041 Uiso 1 1 calc R . .
H12C H 0.2143 1.1480 0.0750 0.041 Uiso 1 1 calc R . .
C13 C 1.0005(4) 0.5835(3) 0.3495(3) 0.0267(10) Uani 1 1 d . . .
H13A H 1.0608 0.5712 0.2930 0.040 Uiso 1 1 calc R . .
H13B H 0.9625 0.5213 0.3933 0.040 Uiso 1 1 calc R . .
H13C H 1.0489 0.6005 0.3892 0.040 Uiso 1 1 calc R . .
C14 C 0.9332(4) 0.7610(3) 0.2590(3) 0.0218(10) Uani 1 1 d . . .
C15 C 0.8181(4) 0.9397(3) 0.1811(3) 0.0200(9) Uani 1 1 d . . .
C16 C 0.9390(3) 1.0818(3) 0.1326(3) 0.0200(9) Uani 1 1 d . . .
C17 C 0.9225(4) 1.1530(3) 0.0352(3) 0.0229(10) Uani 1 1 d . . .
H17A H 0.9018 1.1325 -0.0130 0.027 Uiso 1 1 calc R . .
C18 C 0.9362(4) 1.2541(3) 0.0082(3) 0.0269(10) Uani 1 1 d . . .
H18A H 0.9260 1.3032 -0.0589 0.032 Uiso 1 1 calc R . .
C19 C 0.9649(4) 1.2834(3) 0.0796(3) 0.0281(10) Uani 1 1 d . . .
H19A H 0.9740 1.3530 0.0608 0.034 Uiso 1 1 calc R . .
C20 C 0.9805(4) 1.2135(3) 0.1773(3) 0.0266(10) Uani 1 1 d . . .
H20A H 0.9987 1.2348 0.2258 0.032 Uiso 1 1 calc R . .
C21 C 0.9692(4) 1.1114(3) 0.2041(3) 0.0216(10) Uani 1 1 d . . .
C22 C 1.0835(4) 1.0044(3) 0.3560(3) 0.0225(10) Uani 1 1 d . . .
C23 C 0.9847(4) 0.8511(3) 0.4768(3) 0.0227(10) Uani 1 1 d . . .
C24 C 0.9215(4) 0.7000(3) 0.6067(3) 0.0345(11) Uani 1 1 d . . .
H24A H 0.8379 0.7363 0.6291 0.052 Uiso 1 1 calc R . .
H24B H 0.9545 0.6409 0.6653 0.052 Uiso 1 1 calc R . .
H24C H 0.9077 0.6758 0.5567 0.052 Uiso 1 1 calc R . .
C25 C 0.6660(4) 0.3860(3) 0.2232(3) 0.0281(10) Uani 1 1 d . . .
H25A H 0.7203 0.3208 0.2211 0.034 Uiso 1 1 calc R . .
H25B H 0.5751 0.3737 0.2534 0.034 Uiso 1 1 calc R . .
C26 C 0.7231(4) 0.4250(3) 0.2847(3) 0.0309(11) Uani 1 1 d . . .
H26A H 0.7669 0.3673 0.3404 0.037 Uiso 1 1 calc R . .
H26B H 0.6546 0.4689 0.3137 0.037 Uiso 1 1 calc R . .
C27 C 0.8225(4) 0.4875(3) 0.2039(3) 0.0322(11) Uani 1 1 d . . .
H27A H 0.8402 0.5414 0.2223 0.039 Uiso 1 1 calc R . .
H27B H 0.9065 0.4425 0.1940 0.039 Uiso 1 1 calc R . .
C28 C 0.7534(4) 0.5346(3) 0.1101(3) 0.0329(11) Uani 1 1 d . . .
H28A H 0.7025 0.6036 0.1033 0.040 Uiso 1 1 calc R . .
H28B H 0.8182 0.5421 0.0484 0.040 Uiso 1 1 calc R . .
C29 C 0.4097(4) 0.8096(3) 0.4674(3) 0.0336(11) Uani 1 1 d . . .
H29A H 0.3758 0.8357 0.4013 0.040 Uiso 1 1 calc R . .
H29B H 0.4391 0.7341 0.4896 0.040 Uiso 1 1 calc R . .
C30 C 0.5217(4) 0.8621(3) 0.4578(3) 0.0321(11) Uani 1 1 d . . .
H30A H 0.5104 0.9339 0.4070 0.039 Uiso 1 1 calc R . .
H30B H 0.6073 0.8239 0.4389 0.039 Uiso 1 1 calc R . .
C31 C 0.5104(4) 0.8586(3) 0.5647(3) 0.0317(11) Uani 1 1 d . . .
H31A H 0.5541 0.9116 0.5655 0.038 Uiso 1 1 calc R . .
H31B H 0.5481 0.7898 0.6119 0.038 Uiso 1 1 calc R . .
C32 C 0.3618(4) 0.8816(3) 0.5910(3) 0.0314(11) Uani 1 1 d . . .
H32A H 0.3363 0.8526 0.6656 0.038 Uiso 1 1 calc R . .
H32B H 0.3300 0.9569 0.5646 0.038 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
S1 C3 1.673(4) . ?
S2 C10 1.673(4) . ?
S3 C15 1.656(4) . ?
S4 C22 1.662(4) . ?
O1 C2 1.215(5) . ?
O2 C2 1.328(5) . ?
O2 C1 1.460(5) . ?
O3 C11 1.220(5) . ?
O4 C11 1.331(5) . ?
O4 C12 1.456(5) . ?
O5 C14 1.213(5) . ?
O6 C14 1.340(5) . ?
O6 C13 1.441(4) . ?
O7 C23 1.211(5) . ?
O8 C23 1.336(5) . ?
O8 C24 1.452(5) . ?
O9 C25 1.436(5) . ?
O9 C28 1.440(5) . ?
O10 C32 1.442(5) . ?
O10 C29 1.450(5) . ?
N1 C2 1.382(5) . ?
N1 C3 1.384(5) . ?
N1 H1 0.894(19) . ?
N2 C3 1.345(5) . ?
N2 C4 1.409(5) . ?
N2 H2 0.902(19) . ?
N3 C10 1.351(5) . ?
N3 C9 1.431(5) . ?
N3 H3 0.896(19) . ?
N4 C11 1.369(5) . ?
N4 C10 1.378(5) . ?
N4 H4 0.903(19) . ?
N5 C14 1.363(5) . ?
N5 C15 1.382(5) . ?
N5 H5 0.893(19) . ?
N6 C15 1.345(5) . ?
N6 C16 1.433(5) . ?
N6 H6 0.891(19) . ?
N7 C22 1.351(5) . ?
N7 C21 1.426(5) . ?
N7 H7 0.896(19) . ?
N8 C23 1.381(5) . ?
N8 C22 1.391(5) . ?
N8 H8 0.907(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.395(6) . ?
C4 C9 1.399(5) . ?
C5 C6 1.376(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.396(5) . ?
C8 H8A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 C17 1.381(5) . ?
C16 C21 1.399(5) . ?
C17 C18 1.383(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.386(6) . ?
C18 H18A 0.9500 . ?
C19 C20 1.379(6) . ?
C19 H19A 0.9500 . ?
C20 C21 1.388(5) . ?
C20 H20A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.517(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.529(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.510(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.502(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.520(6) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.521(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 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
C2 O2 C1 113.7(3) . . ?
C11 O4 C12 116.4(3) . . ?
C14 O6 C13 115.7(3) . . ?
C23 O8 C24 114.6(3) . . ?
C25 O9 C28 109.6(3) . . ?
C32 O10 C29 108.7(3) . . ?
C2 N1 C3 126.7(3) . . ?
C2 N1 H1 118(3) . . ?
C3 N1 H1 115(3) . . ?
C3 N2 C4 129.2(3) . . ?
C3 N2 H2 112(3) . . ?
C4 N2 H2 118(3) . . ?
C10 N3 C9 121.5(3) . . ?
C10 N3 H3 116(2) . . ?
C9 N3 H3 122(2) . . ?
C11 N4 C10 127.8(3) . . ?
C11 N4 H4 122(3) . . ?
C10 N4 H4 110(3) . . ?
C14 N5 C15 128.3(3) . . ?
C14 N5 H5 112(3) . . ?
C15 N5 H5 119(3) . . ?
C15 N6 C16 123.5(3) . . ?
C15 N6 H6 114(3) . . ?
C16 N6 H6 122(3) . . ?
C22 N7 C21 126.5(3) . . ?
C22 N7 H7 110(3) . . ?
C21 N7 H7 122(3) . . ?
C23 N8 C22 127.0(3) . . ?
C23 N8 H8 116(3) . . ?
C22 N8 H8 116(3) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 125.0(4) . . ?
O1 C2 N1 125.4(4) . . ?
O2 C2 N1 109.5(3) . . ?
N2 C3 N1 114.7(3) . . ?
N2 C3 S1 126.4(3) . . ?
N1 C3 S1 118.9(3) . . ?
C5 C4 C9 119.3(4) . . ?
C5 C4 N2 123.6(3) . . ?
C9 C4 N2 117.0(3) . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C8 C7 C6 119.8(4) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C7 C8 C9 120.0(4) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 C4 119.9(4) . . ?
C8 C9 N3 120.2(3) . . ?
C4 C9 N3 119.9(3) . . ?
N3 C10 N4 117.7(3) . . ?
N3 C10 S2 122.8(3) . . ?
N4 C10 S2 119.5(3) . . ?
O3 C11 O4 126.1(3) . . ?
O3 C11 N4 125.6(4) . . ?
O4 C11 N4 108.3(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 123.9(4) . . ?
O5 C14 N5 126.0(4) . . ?
O6 C14 N5 110.1(3) . . ?
N6 C15 N5 115.6(3) . . ?
N6 C15 S3 124.7(3) . . ?
N5 C15 S3 119.7(3) . . ?
C17 C16 C21 120.4(4) . . ?
C17 C16 N6 121.8(3) . . ?
C21 C16 N6 117.7(3) . . ?
C16 C17 C18 119.8(4) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
C19 C20 C21 119.3(4) . . ?
C19 C20 H20A 120.3 . . ?
C21 C20 H20A 120.3 . . ?
C20 C21 C16 119.6(4) . . ?
C20 C21 N7 123.4(3) . . ?
C16 C21 N7 116.9(3) . . ?
N7 C22 N8 114.5(3) . . ?
N7 C22 S4 126.2(3) . . ?
N8 C22 S4 119.2(3) . . ?
O7 C23 O8 124.2(4) . . ?
O7 C23 N8 126.3(4) . . ?
O8 C23 N8 109.5(3) . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O9 C25 C26 105.9(3) . . ?
O9 C25 H25A 110.5 . . ?
C26 C25 H25A 110.5 . . ?
O9 C25 H25B 110.5 . . ?
C26 C25 H25B 110.5 . . ?
H25A C25 H25B 108.7 . . ?
C25 C26 C27 101.5(3) . . ?
C25 C26 H26A 111.5 . . ?
C27 C26 H26A 111.5 . . ?
C25 C26 H26B 111.5 . . ?
C27 C26 H26B 111.5 . . ?
H26A C26 H26B 109.3 . . ?
C28 C27 C26 102.6(4) . . ?
C28 C27 H27A 111.2 . . ?
C26 C27 H27A 111.2 . . ?
C28 C27 H27B 111.2 . . ?
C26 C27 H27B 111.2 . . ?
H27A C27 H27B 109.2 . . ?
O9 C28 C27 106.5(3) . . ?
O9 C28 H28A 110.4 . . ?
C27 C28 H28A 110.4 . . ?
O9 C28 H28B 110.4 . . ?
C27 C28 H28B 110.4 . . ?
H28A C28 H28B 108.6 . . ?
O10 C29 C30 106.5(3) . . ?
O10 C29 H29A 110.4 . . ?
C30 C29 H29A 110.4 . . ?
O10 C29 H29B 110.4 . . ?
C30 C29 H29B 110.4 . . ?
H29A C29 H29B 108.6 . . ?
C29 C30 C31 101.6(3) . . ?
C29 C30 H30A 111.4 . . ?
C31 C30 H30A 111.4 . . ?
C29 C30 H30B 111.4 . . ?
C31 C30 H30B 111.4 . . ?
H30A C30 H30B 109.3 . . ?
C30 C31 C32 101.3(3) . . ?
C30 C31 H31A 111.5 . . ?
C32 C31 H31A 111.5 . . ?
C30 C31 H31B 111.5 . . ?
C32 C31 H31B 111.5 . . ?
H31A C31 H31B 109.3 . . ?
O10 C32 C31 105.2(3) . . ?
O10 C32 H32A 110.7 . . ?
C31 C32 H32A 110.7 . . ?
O10 C32 H32B 110.7 . . ?
C31 C32 H32B 110.7 . . ?
H32A C32 H32B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 5.2(5) . . . . ?
C1 O2 C2 N1 -175.2(3) . . . . ?
C3 N1 C2 O1 -3.4(6) . . . . ?
C3 N1 C2 O2 177.0(3) . . . . ?
C4 N2 C3 N1 -178.1(3) . . . . ?
C4 N2 C3 S1 3.6(6) . . . . ?
C2 N1 C3 N2 -2.8(5) . . . . ?
C2 N1 C3 S1 175.7(3) . . . . ?
C3 N2 C4 C5 40.2(6) . . . . ?
C3 N2 C4 C9 -143.8(4) . . . . ?
C9 C4 C5 C6 0.5(5) . . . . ?
N2 C4 C5 C6 176.3(3) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C7 C8 C9 C4 1.1(5) . . . . ?
C7 C8 C9 N3 179.7(3) . . . . ?
C5 C4 C9 C8 -1.1(5) . . . . ?
N2 C4 C9 C8 -177.2(3) . . . . ?
C5 C4 C9 N3 -179.7(3) . . . . ?
N2 C4 C9 N3 4.2(5) . . . . ?
C10 N3 C9 C8 87.1(4) . . . . ?
C10 N3 C9 C4 -94.3(4) . . . . ?
C9 N3 C10 N4 -177.8(3) . . . . ?
C9 N3 C10 S2 2.9(5) . . . . ?
C11 N4 C10 N3 -2.1(5) . . . . ?
C11 N4 C10 S2 177.1(3) . . . . ?
C12 O4 C11 O3 2.4(5) . . . . ?
C12 O4 C11 N4 -178.9(3) . . . . ?
C10 N4 C11 O3 0.6(6) . . . . ?
C10 N4 C11 O4 -178.1(3) . . . . ?
C13 O6 C14 O5 -2.1(5) . . . . ?
C13 O6 C14 N5 177.9(3) . . . . ?
C15 N5 C14 O5 -11.6(6) . . . . ?
C15 N5 C14 O6 168.3(3) . . . . ?
C16 N6 C15 N5 -171.6(3) . . . . ?
C16 N6 C15 S3 8.7(5) . . . . ?
C14 N5 C15 N6 9.3(5) . . . . ?
C14 N5 C15 S3 -171.0(3) . . . . ?
C15 N6 C16 C17 -75.0(5) . . . . ?
C15 N6 C16 C21 107.8(4) . . . . ?
C21 C16 C17 C18 0.1(6) . . . . ?
N6 C16 C17 C18 -177.1(3) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C19 C20 C21 1.0(6) . . . . ?
C19 C20 C21 C16 -1.7(6) . . . . ?
C19 C20 C21 N7 -177.8(4) . . . . ?
C17 C16 C21 C20 1.1(6) . . . . ?
N6 C16 C21 C20 178.4(3) . . . . ?
C17 C16 C21 N7 177.5(3) . . . . ?
N6 C16 C21 N7 -5.2(5) . . . . ?
C22 N7 C21 C20 -59.2(5) . . . . ?
C22 N7 C21 C16 124.6(4) . . . . ?
C21 N7 C22 N8 -169.2(3) . . . . ?
C21 N7 C22 S4 10.4(6) . . . . ?
C23 N8 C22 N7 7.9(5) . . . . ?
C23 N8 C22 S4 -171.8(3) . . . . ?
C24 O8 C23 O7 -5.1(5) . . . . ?
C24 O8 C23 N8 175.4(3) . . . . ?
C22 N8 C23 O7 -4.5(6) . . . . ?
C22 N8 C23 O8 175.0(3) . . . . ?
C28 O9 C25 C26 16.8(4) . . . . ?
O9 C25 C26 C27 -33.0(4) . . . . ?
C25 C26 C27 C28 36.3(4) . . . . ?
C25 O9 C28 C27 7.1(4) . . . . ?
C26 C27 C28 O9 -27.5(4) . . . . ?
C32 O10 C29 C30 -9.6(4) . . . . ?
O10 C29 C30 C31 31.3(4) . . . . ?
C29 C30 C31 C32 -39.8(4) . . . . ?
C29 O10 C32 C31 -16.3(4) . . . . ?
C30 C31 C32 O10 35.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.902(19) 1.84(3) 2.619(4) 144(4) .
N3 H3 O3 0.896(19) 2.00(3) 2.711(4) 135(3) .
N4 H4 S3 0.903(19) 2.52(2) 3.380(3) 159(3) .
N5 H5 S2 0.893(19) 2.40(2) 3.287(3) 171(4) .
N6 H6 O5 0.891(19) 1.95(3) 2.698(4) 140(3) .
N7 H7 O7 0.896(19) 1.86(3) 2.654(4) 147(4) .
N1 H1 O9 0.894(19) 1.93(2) 2.816(4) 173(4) 2_665
N3 H3 O5 0.896(19) 2.25(3) 2.956(4) 135(3) 1_455
N6 H6 O3 0.891(19) 2.30(3) 2.964(4) 131(3) 1_655
N8 H8 O10 0.907(19) 1.95(2) 2.852(4) 174(4) 1_655

_diffrn_measured_fraction_theta_max 0.851
_diffrn_reflns_theta_full        57.27
_diffrn_measured_fraction_theta_full 0.851
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.085

data_TM_dioxane
_database_code_depnum_ccdc_archive 'CCDC 724472'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, dioxane'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C4 H8 O2'
_chemical_formula_sum            'C16 H22 N4 O6 S2'
_chemical_formula_weight         430.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   21.970(10)
_cell_length_b                   11.428(5)
_cell_length_c                   17.147(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.244(18)
_cell_angle_gamma                90.00
_cell_volume                     4012(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    2.773
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7612
_exptl_absorpt_correction_T_max  0.7612
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7583
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.63
_diffrn_reflns_theta_max         58.11
_reflns_number_total             2484
_reflns_number_gt                2163
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.1457P)²+2.9514P] 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     SHELXL
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2484
_refine_ls_number_parameters     268
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1954
_refine_ls_wR_factor_gt          0.1866
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.00101(5) 0.14840(9) -0.07310(5) 0.0321(5) Uani 1 1 d . . .
S2 S 0.16960(4) 0.52104(9) 0.16624(5) 0.0287(5) Uani 1 1 d . . .
O1 O 0.09913(13) 0.2456(2) 0.20309(15) 0.0332(8) Uani 1 1 d . . .
O2 O 0.06387(12) 0.0651(2) 0.21851(15) 0.0319(7) Uani 1 1 d . . .
O3 O 0.29409(11) 0.2532(2) 0.09219(15) 0.0254(7) Uani 1 1 d . . .
O4 O 0.36153(11) 0.2897(2) 0.22446(14) 0.0275(7) Uani 1 1 d . . .
O5 O 0.18549(13) 0.9352(3) 0.15322(15) 0.0354(8) Uani 1 1 d . . .
O6 O 0.19902(13) 0.9135(3) -0.00376(17) 0.0445(9) Uani 1 1 d . . .
N1 N 0.04130(14) 0.1302(3) 0.09076(18) 0.0269(8) Uani 1 1 d D . .
H1 H 0.0257(19) 0.055(2) 0.080(2) 0.032 Uiso 1 1 d D . .
N2 N 0.06543(14) 0.3053(3) 0.04168(18) 0.0245(8) Uani 1 1 d D . .
H2 H 0.0866(17) 0.322(3) 0.0948(13) 0.029 Uiso 1 1 d D . .
N3 N 0.18621(13) 0.3909(3) 0.04725(18) 0.0226(8) Uani 1 1 d D . .
H3 H 0.2098(17) 0.342(3) 0.029(2) 0.027 Uiso 1 1 d D . .
N4 N 0.26903(13) 0.3851(3) 0.17729(18) 0.0250(8) Uani 1 1 d D . .
H4 H 0.2829(18) 0.413(3) 0.2298(14) 0.030 Uiso 1 1 d D . .
C1 C 0.0960(2) 0.0759(4) 0.3084(2) 0.0353(11) Uani 1 1 d . . .
H1A H 0.1432 0.0831 0.3224 0.053 Uiso 1 1 calc R . .
H1B H 0.0868 0.0064 0.3357 0.053 Uiso 1 1 calc R . .
H1C H 0.0797 0.1456 0.3278 0.053 Uiso 1 1 calc R . .
C2 C 0.07111(16) 0.1562(4) 0.1741(2) 0.0258(10) Uani 1 1 d . . .
C3 C 0.03783(16) 0.2004(3) 0.0234(2) 0.0239(9) Uani 1 1 d . . .
C4 C 0.06746(17) 0.3907(3) -0.0179(2) 0.0225(9) Uani 1 1 d . . .
C5 C 0.01012(17) 0.4339(3) -0.0782(2) 0.0245(9) Uani 1 1 d . . .
H5 H -0.0312 0.4045 -0.0814 0.029 Uiso 1 1 calc R . .
C6 C 0.01398(18) 0.5192(3) -0.1326(2) 0.0289(10) Uani 1 1 d . . .
H6 H -0.0249 0.5470 -0.1745 0.035 Uiso 1 1 calc R . .
C7 C 0.07379(18) 0.5655(3) -0.1276(2) 0.0259(9) Uani 1 1 d . . .
H7 H 0.0758 0.6247 -0.1655 0.031 Uiso 1 1 calc R . .
C8 C 0.13022(18) 0.5244(3) -0.0670(2) 0.0252(10) Uani 1 1 d . . .
H8 H 0.1713 0.5566 -0.0621 0.030 Uiso 1 1 calc R . .
C9 C 0.12697(16) 0.4359(3) -0.0132(2) 0.0215(9) Uani 1 1 d . . .
C10 C 0.20890(16) 0.4280(3) 0.1262(2) 0.0222(9) Uani 1 1 d . . .
C11 C 0.30678(16) 0.3038(3) 0.1579(2) 0.0226(9) Uani 1 1 d . . .
C12 C 0.40712(16) 0.2040(4) 0.2164(2) 0.0286(10) Uani 1 1 d . . .
H12A H 0.3870 0.1262 0.2088 0.043 Uiso 1 1 calc R . .
H12B H 0.4465 0.2044 0.2672 0.043 Uiso 1 1 calc R . .
H12C H 0.4188 0.2231 0.1679 0.043 Uiso 1 1 calc R . .
C13 C 0.2061(3) 0.8280(4) 0.1274(3) 0.0552(14) Uani 1 1 d . . .
H13A H 0.1910 0.7612 0.1523 0.066 Uiso 1 1 calc R . .
H13B H 0.2544 0.8256 0.1479 0.066 Uiso 1 1 calc R . .
C14 C 0.1794(3) 0.8166(5) 0.0339(3) 0.0619(16) Uani 1 1 d . . .
H14A H 0.1954 0.7431 0.0176 0.074 Uiso 1 1 calc R . .
H14B H 0.1311 0.8130 0.0136 0.074 Uiso 1 1 calc R . .
C15 C 0.1782(2) 1.0194(5) 0.0227(3) 0.0454(13) Uani 1 1 d . . .
H15A H 0.1299 1.0207 0.0029 0.054 Uiso 1 1 calc R . .
H15B H 0.1925 1.0868 -0.0025 0.054 Uiso 1 1 calc R . .
C16 C 0.20534(19) 1.0305(4) 0.1152(2) 0.0320(10) Uani 1 1 d . . .
H16A H 0.2536 1.0328 0.1349 0.038 Uiso 1 1 calc R . .
H16B H 0.1901 1.1047 0.1318 0.038 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
S1 C3 1.666(4) . ?
S2 C10 1.667(4) . ?
O1 C2 1.203(5) . ?
O2 C2 1.333(5) . ?
O2 C1 1.449(4) . ?
O3 C11 1.205(4) . ?
O4 C11 1.335(4) . ?
O4 C12 1.443(4) . ?
O5 C16 1.417(5) . ?
O5 C13 1.430(6) . ?
O6 C14 1.425(6) . ?
O6 C15 1.425(6) . ?
N1 C2 1.372(5) . ?
N1 C3 1.385(5) . ?
N1 H1 0.916(19) . ?
N2 C3 1.329(5) . ?
N2 C4 1.426(5) . ?
N2 H2 0.880(19) . ?
N3 C10 1.331(5) . ?
N3 C9 1.434(4) . ?
N3 H3 0.886(19) . ?
N4 C11 1.365(5) . ?
N4 C10 1.384(4) . ?
N4 H4 0.897(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C9 1.380(5) . ?
C4 C5 1.398(5) . ?
C5 C6 1.373(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.500(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.483(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C2 O2 C1 115.3(3) . . ?
C11 O4 C12 116.2(3) . . ?
C16 O5 C13 109.3(3) . . ?
C14 O6 C15 109.3(3) . . ?
C2 N1 C3 127.2(3) . . ?
C2 N1 H1 114(2) . . ?
C3 N1 H1 118(2) . . ?
C3 N2 C4 125.4(3) . . ?
C3 N2 H2 117(3) . . ?
C4 N2 H2 117(3) . . ?
C10 N3 C9 121.9(3) . . ?
C10 N3 H3 120(3) . . ?
C9 N3 H3 118(3) . . ?
C11 N4 C10 127.7(3) . . ?
C11 N4 H4 118(3) . . ?
C10 N4 H4 114(3) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 125.2(3) . . ?
O1 C2 N1 126.4(3) . . ?
O2 C2 N1 108.4(3) . . ?
N2 C3 N1 116.3(3) . . ?
N2 C3 S1 124.9(3) . . ?
N1 C3 S1 118.8(3) . . ?
C9 C4 C5 119.5(3) . . ?
C9 C4 N2 119.3(3) . . ?
C5 C4 N2 121.2(3) . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.0(4) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 120.6(3) . . ?
C4 C9 N3 120.1(3) . . ?
C8 C9 N3 119.4(3) . . ?
N3 C10 N4 116.8(3) . . ?
N3 C10 S2 124.3(3) . . ?
N4 C10 S2 118.9(3) . . ?
O3 C11 O4 125.0(3) . . ?
O3 C11 N4 126.8(3) . . ?
O4 C11 N4 108.2(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 C14 111.1(4) . . ?
O5 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
O5 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O6 C14 C13 110.5(4) . . ?
O6 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O6 C15 C16 111.2(4) . . ?
O6 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
O6 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O5 C16 C15 110.7(3) . . ?
O5 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 -3.4(5) . . . . ?
C1 O2 C2 N1 176.7(3) . . . . ?
C3 N1 C2 O1 0.6(6) . . . . ?
C3 N1 C2 O2 -179.4(3) . . . . ?
C4 N2 C3 N1 179.9(3) . . . . ?
C4 N2 C3 S1 0.7(5) . . . . ?
C2 N1 C3 N2 -1.3(5) . . . . ?
C2 N1 C3 S1 177.9(3) . . . . ?
C3 N2 C4 C9 -125.2(4) . . . . ?
C3 N2 C4 C5 58.2(5) . . . . ?
C9 C4 C5 C6 1.1(6) . . . . ?
N2 C4 C5 C6 177.7(3) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C5 C6 C7 C8 0.3(6) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C5 C4 C9 C8 0.6(6) . . . . ?
N2 C4 C9 C8 -176.0(3) . . . . ?
C5 C4 C9 N3 -178.8(3) . . . . ?
N2 C4 C9 N3 4.6(5) . . . . ?
C7 C8 C9 C4 -2.0(6) . . . . ?
C7 C8 C9 N3 177.5(3) . . . . ?
C10 N3 C9 C4 -83.2(5) . . . . ?
C10 N3 C9 C8 97.4(4) . . . . ?
C9 N3 C10 N4 -175.1(3) . . . . ?
C9 N3 C10 S2 5.1(5) . . . . ?
C11 N4 C10 N3 -3.9(6) . . . . ?
C11 N4 C10 S2 175.9(3) . . . . ?
C12 O4 C11 O3 -2.2(5) . . . . ?
C12 O4 C11 N4 178.4(3) . . . . ?
C10 N4 C11 O3 -0.8(6) . . . . ?
C10 N4 C11 O4 178.6(3) . . . . ?
C16 O5 C13 C14 -57.2(5) . . . . ?
C15 O6 C14 C13 -56.8(5) . . . . ?
O5 C13 C14 O6 57.5(6) . . . . ?
C14 O6 C15 C16 58.0(4) . . . . ?
C13 O5 C16 C15 57.7(4) . . . . ?
O6 C15 C16 O5 -59.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.880(19) 1.98(3) 2.681(4) 136(3) .
N2 H2 S2 0.880(19) 2.90(3) 3.512(3) 128(3) .
N3 H3 O3 0.886(19) 2.04(3) 2.713(4) 131(3) .
N1 H1 S1 0.916(19) 2.39(2) 3.299(4) 171(4) 5
N3 H3 O3 0.886(19) 2.33(3) 3.060(4) 140(3) 7
N4 H4 O5 0.897(19) 1.89(2) 2.769(4) 167(4) 4_545

_diffrn_measured_fraction_theta_max 0.882
_diffrn_reflns_theta_full        58.11
_diffrn_measured_fraction_theta_full 0.881
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.102

data_TM_pyridine
_database_code_depnum_ccdc_archive 'CCDC 724473'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, pyridine'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C5 H5 N1'
_chemical_formula_sum            'C17 H19 N5 O4 S2'
_chemical_formula_weight         421.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.2439(10)
_cell_length_b                   10.6899(12)
_cell_length_c                   12.4925(15)
_cell_angle_alpha                67.892(5)
_cell_angle_beta                 81.442(6)
_cell_angle_gamma                74.153(5)
_cell_volume                     979.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    2.768
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7616
_exptl_absorpt_correction_T_max  0.7616
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7870
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         57.87
_reflns_number_total             2437
_reflns_number_gt                2305
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0667P)²+0.3525P] 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     SHELXL
_refine_ls_extinction_coef       0.0410(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2437
_refine_ls_number_parameters     266
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16632(7) 0.34305(6) 0.38703(5) 0.0238(3) Uani 1 1 d . . .
S2 S 0.60654(7) 0.10217(6) 0.08083(5) 0.0220(3) Uani 1 1 d . . .
O1 O 0.31522(19) 0.53236(16) 0.00309(13) 0.0207(4) Uani 1 1 d . . .
O2 O 0.04029(19) 0.64645(16) -0.00094(13) 0.0204(4) Uani 1 1 d . . .
O3 O 0.14988(19) -0.03940(16) 0.30075(13) 0.0217(4) Uani 1 1 d . . .
O4 O 0.1228(2) -0.08763(17) 0.14399(14) 0.0230(4) Uani 1 1 d . . .
N1 N 0.1409(2) 0.5054(2) 0.16825(16) 0.0173(5) Uani 1 1 d D . .
H1 H 0.035(2) 0.532(2) 0.193(2) 0.021 Uiso 1 1 d D . .
N2 N 0.4051(2) 0.35773(19) 0.21744(16) 0.0168(5) Uani 1 1 d D . .
H2 H 0.435(3) 0.392(3) 0.1436(15) 0.020 Uiso 1 1 d D . .
N3 N 0.4151(2) 0.0719(2) 0.27528(16) 0.0172(5) Uani 1 1 d D . .
H3 H 0.325(3) 0.047(2) 0.3175(19) 0.021 Uiso 1 1 d D . .
N4 N 0.3242(2) 0.0156(2) 0.13614(16) 0.0177(5) Uani 1 1 d D . .
H4 H 0.353(3) 0.001(2) 0.0710(16) 0.021 Uiso 1 1 d D . .
C1 C 0.0638(3) 0.7112(3) -0.12570(19) 0.0221(6) Uani 1 1 d . . .
H1A H -0.0430 0.7733 -0.1574 0.033 Uiso 1 1 calc R . .
H1B H 0.1006 0.6391 -0.1605 0.033 Uiso 1 1 calc R . .
H1C H 0.1498 0.7648 -0.1432 0.033 Uiso 1 1 calc R . .
C2 C 0.1799(3) 0.5592(2) 0.0516(2) 0.0169(6) Uani 1 1 d . . .
C3 C 0.2462(3) 0.4030(2) 0.25134(19) 0.0167(6) Uani 1 1 d . . .
C4 C 0.5243(3) 0.2520(2) 0.29654(18) 0.0148(5) Uani 1 1 d . . .
C5 C 0.6364(3) 0.2891(2) 0.34475(19) 0.0174(6) Uani 1 1 d . . .
H5 H 0.6312 0.3844 0.3278 0.021 Uiso 1 1 calc R . .
C6 C 0.7562(3) 0.1874(2) 0.41773(19) 0.0190(6) Uani 1 1 d . . .
H6 H 0.8331 0.2134 0.4503 0.023 Uiso 1 1 calc R . .
C7 C 0.7641(3) 0.0486(2) 0.44319(19) 0.0186(6) Uani 1 1 d . . .
H7 H 0.8467 -0.0209 0.4929 0.022 Uiso 1 1 calc R . .
C8 C 0.6506(3) 0.0106(2) 0.39582(19) 0.0174(6) Uani 1 1 d . . .
H8 H 0.6546 -0.0848 0.4140 0.021 Uiso 1 1 calc R . .
C9 C 0.5321(3) 0.1123(2) 0.32227(18) 0.0150(5) Uani 1 1 d . . .
C10 C 0.4421(3) 0.0620(2) 0.17027(19) 0.0160(5) Uani 1 1 d . . .
C11 C 0.1940(3) -0.0377(2) 0.2034(2) 0.0174(6) Uani 1 1 d . . .
C12 C -0.0110(3) -0.1545(3) 0.2053(2) 0.0273(6) Uani 1 1 d . . .
H12A H -0.0547 -0.1874 0.1546 0.041 Uiso 1 1 calc R . .
H12B H -0.1022 -0.0879 0.2291 0.041 Uiso 1 1 calc R . .
H12C H 0.0329 -0.2336 0.2739 0.041 Uiso 1 1 calc R . .
N20 N 0.2067(2) 0.3954(2) 0.75918(16) 0.0193(5) Uani 1 1 d . . .
C20 C 0.3374(3) 0.3567(2) 0.8253(2) 0.0214(6) Uani 1 1 d . . .
H20 H 0.3150 0.3486 0.9042 0.026 Uiso 1 1 calc R . .
C21 C 0.5042(3) 0.3275(2) 0.7850(2) 0.0228(6) Uani 1 1 d . . .
H21 H 0.5937 0.3029 0.8344 0.027 Uiso 1 1 calc R . .
C22 C 0.5373(3) 0.3349(2) 0.6714(2) 0.0248(6) Uani 1 1 d . . .
H22 H 0.6503 0.3159 0.6410 0.030 Uiso 1 1 calc R . .
C23 C 0.4036(3) 0.3704(2) 0.6026(2) 0.0226(6) Uani 1 1 d . . .
H23 H 0.4228 0.3736 0.5248 0.027 Uiso 1 1 calc R . .
C24 C 0.2422(3) 0.4012(2) 0.6488(2) 0.0208(6) Uani 1 1 d . . .
H24 H 0.1508 0.4279 0.6004 0.025 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
S1 C3 1.673(2) . ?
S2 C10 1.666(2) . ?
O1 C2 1.204(3) . ?
O2 C2 1.343(3) . ?
O2 C1 1.455(3) . ?
O3 C11 1.212(3) . ?
O4 C11 1.334(3) . ?
O4 C12 1.443(3) . ?
N1 C2 1.374(3) . ?
N1 C3 1.387(3) . ?
N1 H1 0.888(17) . ?
N2 C3 1.331(3) . ?
N2 C4 1.436(3) . ?
N2 H2 0.879(17) . ?
N3 C10 1.337(3) . ?
N3 C9 1.431(3) . ?
N3 H3 0.886(17) . ?
N4 C11 1.374(3) . ?
N4 C10 1.385(3) . ?
N4 H4 0.871(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.385(3) . ?
C4 C9 1.389(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N20 C20 1.334(3) . ?
N20 C24 1.347(3) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 H24 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
C2 O2 C1 114.42(17) . . ?
C11 O4 C12 115.77(18) . . ?
C2 N1 C3 126.61(19) . . ?
C2 N1 H1 117.9(16) . . ?
C3 N1 H1 115.3(16) . . ?
C3 N2 C4 121.99(19) . . ?
C3 N2 H2 117.8(17) . . ?
C4 N2 H2 120.1(17) . . ?
C10 N3 C9 121.80(19) . . ?
C10 N3 H3 117.7(16) . . ?
C9 N3 H3 120.3(16) . . ?
C11 N4 C10 127.00(19) . . ?
C11 N4 H4 117.8(17) . . ?
C10 N4 H4 113.4(17) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.9(2) . . ?
O1 C2 N1 126.4(2) . . ?
O2 C2 N1 108.63(19) . . ?
N2 C3 N1 117.6(2) . . ?
N2 C3 S1 124.05(18) . . ?
N1 C3 S1 118.39(17) . . ?
C5 C4 C9 119.6(2) . . ?
C5 C4 N2 119.9(2) . . ?
C9 C4 N2 120.5(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 N3 119.2(2) . . ?
C4 C9 N3 120.41(19) . . ?
N3 C10 N4 116.7(2) . . ?
N3 C10 S2 123.84(18) . . ?
N4 C10 S2 119.50(16) . . ?
O3 C11 O4 125.1(2) . . ?
O3 C11 N4 126.0(2) . . ?
O4 C11 N4 108.93(19) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 N20 C24 116.9(2) . . ?
N20 C20 C21 123.4(2) . . ?
N20 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
C22 C21 C20 118.5(2) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 118.7(2) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
N20 C24 C23 123.5(2) . . ?
N20 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 -0.8(3) . . . . ?
C1 O2 C2 N1 -179.96(18) . . . . ?
C3 N1 C2 O1 -4.8(4) . . . . ?
C3 N1 C2 O2 174.30(19) . . . . ?
C4 N2 C3 N1 -179.99(19) . . . . ?
C4 N2 C3 S1 -0.5(3) . . . . ?
C2 N1 C3 N2 4.9(3) . . . . ?
C2 N1 C3 S1 -174.56(17) . . . . ?
C3 N2 C4 C5 -97.7(3) . . . . ?
C3 N2 C4 C9 84.4(3) . . . . ?
C9 C4 C5 C6 0.3(3) . . . . ?
N2 C4 C5 C6 -177.51(19) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C4 -0.8(3) . . . . ?
C7 C8 C9 N3 -179.30(19) . . . . ?
C5 C4 C9 C8 0.2(3) . . . . ?
N2 C4 C9 C8 178.01(19) . . . . ?
C5 C4 C9 N3 178.68(19) . . . . ?
N2 C4 C9 N3 -3.5(3) . . . . ?
C10 N3 C9 C8 -96.3(3) . . . . ?
C10 N3 C9 C4 85.2(3) . . . . ?
C9 N3 C10 N4 177.02(19) . . . . ?
C9 N3 C10 S2 -3.1(3) . . . . ?
C11 N4 C10 N3 -8.7(3) . . . . ?
C11 N4 C10 S2 171.38(17) . . . . ?
C12 O4 C11 O3 -3.4(3) . . . . ?
C12 O4 C11 N4 176.75(18) . . . . ?
C10 N4 C11 O3 8.3(4) . . . . ?
C10 N4 C11 O4 -171.8(2) . . . . ?
C24 N20 C20 C21 2.3(3) . . . . ?
N20 C20 C21 C22 -1.9(4) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 1.9(3) . . . . ?
C20 N20 C24 C23 -0.4(3) . . . . ?
C22 C23 C24 N20 -1.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.879(17) 2.01(2) 2.698(2) 135(2) .
N3 H3 O3 0.886(17) 1.99(2) 2.688(2) 135(2) .
N1 H1 N20 0.888(17) 2.019(17) 2.906(3) 176(2) 2_566
N2 H2 O1 0.879(17) 2.63(2) 3.382(2) 144(2) 2_665
N4 H4 S2 0.871(17) 2.473(18) 3.312(2) 162(2) 2_655

_diffrn_measured_fraction_theta_max 0.892
_diffrn_reflns_theta_full        57.87
_diffrn_measured_fraction_theta_full 0.892
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.094

data_TM_12DCB
_database_code_depnum_ccdc_archive 'CCDC 724474'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, 1,2-dichlorobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C6 H4 Cl2'
_chemical_formula_sum            'C18 H18 Cl2 N4 O4 S2'
_chemical_formula_weight         489.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   7.9951(7)
_cell_length_b                   9.5484(9)
_cell_length_c                   14.7017(11)
_cell_angle_alpha                81.910(4)
_cell_angle_beta                 84.862(4)
_cell_angle_gamma                73.646(4)
_cell_volume                     1064.73(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    4.876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3759
_exptl_absorpt_correction_T_max  0.3759
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7159
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         57.90
_reflns_number_total             2645
_reflns_number_gt                2527
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0707P)²+0.4975P] 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     SHELXL
_refine_ls_extinction_coef       0.0394(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2645
_refine_ls_number_parameters     284
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.202
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50354(9) 0.09760(7) 0.86255(4) 0.0119(3) Uani 1 1 d . . .
S2 S 0.07357(8) 0.41754(7) 0.81120(4) 0.0138(3) Uani 1 1 d . . .
O1 O 0.8848(2) 0.2460(2) 1.01625(12) 0.0147(5) Uani 1 1 d . . .
O2 O 0.8209(3) 0.0759(2) 1.12681(13) 0.0185(5) Uani 1 1 d . . .
O3 O 0.4180(2) 0.3911(2) 1.05018(12) 0.0147(5) Uani 1 1 d . . .
O4 O 0.2238(2) 0.27801(19) 1.12455(12) 0.0113(5) Uani 1 1 d . . .
N1 N 0.7116(3) 0.1005(2) 0.99105(15) 0.0115(6) Uani 1 1 d D . .
H1 H 0.664(3) 0.032(3) 1.0203(19) 0.014 Uiso 1 1 d D . .
N2 N 0.7054(3) 0.2762(2) 0.86402(14) 0.0088(5) Uani 1 1 d D . .
H2 H 0.797(3) 0.295(3) 0.8846(19) 0.011 Uiso 1 1 d D . .
N3 N 0.3646(3) 0.4562(2) 0.86985(15) 0.0083(5) Uani 1 1 d D . .
H3 H 0.424(3) 0.452(3) 0.9175(15) 0.010 Uiso 1 1 d D . .
N4 N 0.1768(3) 0.3768(2) 0.98030(15) 0.0095(5) Uani 1 1 d D . .
H4 H 0.082(3) 0.345(3) 0.9914(19) 0.011 Uiso 1 1 d D . .
C1 C 0.9347(4) 0.1088(4) 1.1880(2) 0.0217(7) Uani 1 1 d . . .
H1A H 0.9312 0.0494 1.2478 0.032 Uiso 1 1 calc R . .
H1B H 0.8950 0.2133 1.1961 0.032 Uiso 1 1 calc R . .
H1C H 1.0546 0.0857 1.1611 0.032 Uiso 1 1 calc R . .
C2 C 0.8135(3) 0.1502(3) 1.04294(19) 0.0110(6) Uani 1 1 d . . .
C3 C 0.6479(3) 0.1644(3) 0.90640(18) 0.0084(6) Uani 1 1 d . . .
C4 C 0.6344(3) 0.3624(3) 0.78137(18) 0.0080(6) Uani 1 1 d . . .
C5 C 0.7369(4) 0.3600(3) 0.70000(18) 0.0101(6) Uani 1 1 d . . .
H5 H 0.8535 0.2990 0.6988 0.012 Uiso 1 1 calc R . .
C6 C 0.6703(4) 0.4458(3) 0.62064(19) 0.0138(6) Uani 1 1 d . . .
H6 H 0.7409 0.4436 0.5650 0.017 Uiso 1 1 calc R . .
C7 C 0.4999(4) 0.5352(3) 0.62244(18) 0.0143(7) Uani 1 1 d . . .
H7 H 0.4539 0.5938 0.5679 0.017 Uiso 1 1 calc R . .
C8 C 0.3962(4) 0.5395(3) 0.70411(18) 0.0111(6) Uani 1 1 d . . .
H8 H 0.2800 0.6012 0.7050 0.013 Uiso 1 1 calc R . .
C9 C 0.4621(3) 0.4540(3) 0.78363(17) 0.0083(6) Uani 1 1 d . . .
C10 C 0.2143(3) 0.4181(3) 0.88808(18) 0.0089(6) Uani 1 1 d . . .
C11 C 0.2848(3) 0.3522(3) 1.05214(18) 0.0087(6) Uani 1 1 d . . .
C12 C 0.3170(4) 0.2577(3) 1.20781(18) 0.0136(6) Uani 1 1 d . . .
H12A H 0.2637 0.2014 1.2572 0.020 Uiso 1 1 calc R . .
H12B H 0.3110 0.3539 1.2261 0.020 Uiso 1 1 calc R . .
H12C H 0.4394 0.2040 1.1964 0.020 Uiso 1 1 calc R . .
C20 C 0.2207(4) 0.0514(3) 1.49100(19) 0.0147(7) Uani 1 1 d . . .
C21 C 0.3271(4) -0.0327(3) 1.5595(2) 0.0224(7) Uani 1 1 d . . .
H21 H 0.3765 -0.1351 1.5571 0.027 Uiso 1 1 calc R . .
C22 C 0.3612(4) 0.0328(3) 1.6316(2) 0.0234(8) Uani 1 1 d . . .
H22 H 0.4330 -0.0252 1.6788 0.028 Uiso 1 1 calc R . .
C23 C 0.2913(4) 0.1820(4) 1.6350(2) 0.0232(8) Uani 1 1 d . . .
H23 H 0.3166 0.2268 1.6839 0.028 Uiso 1 1 calc R . .
C24 C 0.1846(4) 0.2660(3) 1.56688(19) 0.0171(7) Uani 1 1 d . . .
H24 H 0.1356 0.3683 1.5695 0.020 Uiso 1 1 calc R . .
C25 C 0.1489(3) 0.2011(3) 1.49496(18) 0.0131(7) Uani 1 1 d . . .
Cl1 Cl 0.18385(10) -0.03242(8) 1.40043(5) 0.0262(3) Uani 1 1 d . . .
Cl2 Cl 0.01405(9) 0.30943(8) 1.41076(5) 0.0236(3) 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
S1 C3 1.679(3) . ?
S2 C10 1.666(3) . ?
O1 C2 1.212(3) . ?
O2 C2 1.331(3) . ?
O2 C1 1.457(3) . ?
O3 C11 1.219(3) . ?
O4 C11 1.327(3) . ?
O4 C12 1.452(3) . ?
N1 C2 1.379(4) . ?
N1 C3 1.380(3) . ?
N1 H1 0.891(18) . ?
N2 C3 1.333(3) . ?
N2 C4 1.434(3) . ?
N2 H2 0.889(18) . ?
N3 C10 1.345(4) . ?
N3 C9 1.427(3) . ?
N3 H3 0.870(18) . ?
N4 C11 1.377(4) . ?
N4 C10 1.388(4) . ?
N4 H4 0.891(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.387(4) . ?
C4 C9 1.409(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(4) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C20 C21 1.387(4) . ?
C20 C25 1.390(4) . ?
C20 Cl1 1.733(3) . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9500 . ?
C25 Cl2 1.736(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 115.4(2) . . ?
C11 O4 C12 115.2(2) . . ?
C2 N1 C3 127.0(2) . . ?
C2 N1 H1 115.7(19) . . ?
C3 N1 H1 115.8(19) . . ?
C3 N2 C4 122.9(2) . . ?
C3 N2 H2 119.5(18) . . ?
C4 N2 H2 117.5(18) . . ?
C10 N3 C9 125.8(2) . . ?
C10 N3 H3 115.4(19) . . ?
C9 N3 H3 115.2(19) . . ?
C11 N4 C10 127.5(2) . . ?
C11 N4 H4 116.4(18) . . ?
C10 N4 H4 114.7(18) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 125.6(2) . . ?
O1 C2 N1 125.4(2) . . ?
O2 C2 N1 109.0(2) . . ?
N2 C3 N1 117.7(2) . . ?
N2 C3 S1 123.7(2) . . ?
N1 C3 S1 118.60(19) . . ?
C5 C4 C9 119.9(2) . . ?
C5 C4 N2 120.2(2) . . ?
C9 C4 N2 119.8(2) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 119.4(2) . . ?
C8 C9 N3 123.0(2) . . ?
C4 C9 N3 117.6(2) . . ?
N3 C10 N4 115.2(2) . . ?
N3 C10 S2 126.1(2) . . ?
N4 C10 S2 118.73(19) . . ?
O3 C11 O4 124.4(2) . . ?
O3 C11 N4 125.6(2) . . ?
O4 C11 N4 110.0(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C21 C20 C25 119.7(3) . . ?
C21 C20 Cl1 119.0(2) . . ?
C25 C20 Cl1 121.2(2) . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.0(3) . . ?
C24 C25 Cl2 119.1(2) . . ?
C20 C25 Cl2 121.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 -4.2(4) . . . . ?
C1 O2 C2 N1 175.8(2) . . . . ?
C3 N1 C2 O1 -11.6(4) . . . . ?
C3 N1 C2 O2 168.4(2) . . . . ?
C4 N2 C3 N1 -172.5(2) . . . . ?
C4 N2 C3 S1 7.6(3) . . . . ?
C2 N1 C3 N2 8.4(4) . . . . ?
C2 N1 C3 S1 -171.7(2) . . . . ?
C3 N2 C4 C5 -114.8(3) . . . . ?
C3 N2 C4 C9 67.5(3) . . . . ?
C9 C4 C5 C6 -0.7(4) . . . . ?
N2 C4 C5 C6 -178.4(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C7 C8 C9 N3 178.2(2) . . . . ?
C5 C4 C9 C8 0.7(3) . . . . ?
N2 C4 C9 C8 178.4(2) . . . . ?
C5 C4 C9 N3 -177.8(2) . . . . ?
N2 C4 C9 N3 -0.1(3) . . . . ?
C10 N3 C9 C8 61.9(4) . . . . ?
C10 N3 C9 C4 -119.6(3) . . . . ?
C9 N3 C10 N4 157.3(2) . . . . ?
C9 N3 C10 S2 -23.1(4) . . . . ?
C11 N4 C10 N3 -9.3(4) . . . . ?
C11 N4 C10 S2 171.0(2) . . . . ?
C12 O4 C11 O3 6.4(4) . . . . ?
C12 O4 C11 N4 -174.2(2) . . . . ?
C10 N4 C11 O3 16.0(4) . . . . ?
C10 N4 C11 O4 -163.4(2) . . . . ?
C25 C20 C21 C22 0.0(4) . . . . ?
Cl1 C20 C21 C22 178.6(2) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C20 -0.1(4) . . . . ?
C23 C24 C25 Cl2 179.9(2) . . . . ?
C21 C20 C25 C24 0.4(4) . . . . ?
Cl1 C20 C25 C24 -178.2(2) . . . . ?
C21 C20 C25 Cl2 -179.6(2) . . . . ?
Cl1 C20 C25 Cl2 1.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.889(18) 2.06(2) 2.704(3) 128(2) .
N3 H3 O3 0.870(18) 1.96(2) 2.681(3) 140(3) .
N1 H1 S1 0.891(18) 2.49(2) 3.346(2) 161(3) 2_657
N2 H2 S2 0.889(18) 2.85(2) 3.553(2) 138(2) 1_655
N3 H3 O3 0.870(18) 2.33(2) 2.968(3) 130(2) 2_667
N4 H4 O1 0.891(18) 2.034(18) 2.920(3) 173(3) 1_455

_diffrn_measured_fraction_theta_max 0.893
_diffrn_reflns_theta_full        57.90
_diffrn_measured_fraction_theta_full 0.893
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.129

data_TM_benzene
_database_code_depnum_ccdc_archive 'CCDC 724475'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'thiophanate-methyl, benzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N4 O4 S2, C6 H6'
_chemical_formula_sum            'C18 H20 N4 O4 S2'
_chemical_formula_weight         420.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.4106(8)
_cell_length_b                   9.9524(9)
_cell_length_c                   12.9517(12)
_cell_angle_alpha                107.946(4)
_cell_angle_beta                 101.732(5)
_cell_angle_gamma                96.683(4)
_cell_volume                     991.01(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    2.720
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7726
_exptl_absorpt_correction_T_max  0.8760
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8528
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.71
_diffrn_reflns_theta_max         58.06
_reflns_number_total             2494
_reflns_number_gt                2237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
The N-H distances of the hydrogen bonding hydrogens were restrained to 0.91
Å to give the best fit to the X-ray data and to ensure a stable refinement.
;

_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)+(0.0497P)²+0.3689P] 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     SHELXL
_refine_ls_extinction_coef       0.0165(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2494
_refine_ls_number_parameters     268
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17080(8) 0.22742(7) 0.90664(5) 0.0355(2) Uani 1 1 d . . .
S2 S 0.24494(7) 0.39462(6) 0.46318(5) 0.0257(2) Uani 1 1 d . . .
O1 O 0.44715(19) -0.07763(17) 0.70336(13) 0.0278(4) Uani 1 1 d . . .
O2 O 0.56670(18) -0.08619(16) 0.87282(12) 0.0229(4) Uani 1 1 d . . .
O3 O 0.54952(18) 0.31170(17) 0.76600(13) 0.0252(4) Uani 1 1 d . . .
O4 O 0.74727(18) 0.46480(16) 0.74166(12) 0.0226(4) Uani 1 1 d . . .
N1 N 0.3800(2) 0.05286(19) 0.86313(16) 0.0198(5) Uani 1 1 d D . .
H1 H 0.409(3) 0.077(2) 0.9367(14) 0.024 Uiso 1 1 d D . .
N2 N 0.1966(2) 0.0638(2) 0.70819(15) 0.0193(5) Uani 1 1 d D . .
H2 H 0.245(3) 0.005(2) 0.6666(18) 0.023 Uiso 1 1 d D . .
N3 N 0.2554(2) 0.2834(2) 0.63004(16) 0.0199(5) Uani 1 1 d D . .
H3 H 0.325(2) 0.269(2) 0.6855(16) 0.024 Uiso 1 1 d D . .
N4 N 0.4985(2) 0.4108(2) 0.62611(16) 0.0209(5) Uani 1 1 d D . .
H4 H 0.552(3) 0.459(2) 0.5932(19) 0.025 Uiso 1 1 d D . .
C1 C 0.6653(3) -0.1829(3) 0.8180(2) 0.0334(7) Uani 1 1 d . . .
H1A H 0.5924 -0.2616 0.7539 0.050 Uiso 1 1 calc R . .
H1B H 0.7253 -0.2225 0.8715 0.050 Uiso 1 1 calc R . .
H1C H 0.7447 -0.1296 0.7919 0.050 Uiso 1 1 calc R . .
C2 C 0.4631(3) -0.0409(2) 0.8041(2) 0.0209(6) Uani 1 1 d . . .
C3 C 0.2502(3) 0.1103(2) 0.82012(19) 0.0205(6) Uani 1 1 d . . .
C4 C 0.0587(3) 0.1081(2) 0.65082(18) 0.0180(5) Uani 1 1 d . . .
C5 C -0.1011(3) 0.0393(2) 0.63621(19) 0.0237(6) Uani 1 1 d . . .
H5 H -0.1198 -0.0374 0.6641 0.028 Uiso 1 1 calc R . .
C6 C -0.2335(3) 0.0821(3) 0.5811(2) 0.0256(6) Uani 1 1 d . . .
H6 H -0.3433 0.0350 0.5710 0.031 Uiso 1 1 calc R . .
C7 C -0.2061(3) 0.1935(2) 0.54052(18) 0.0236(6) Uani 1 1 d . . .
H7 H -0.2976 0.2233 0.5033 0.028 Uiso 1 1 calc R . .
C8 C -0.0470(3) 0.2623(2) 0.55352(18) 0.0215(5) Uani 1 1 d . . .
H8 H -0.0296 0.3388 0.5253 0.026 Uiso 1 1 calc R . .
C9 C 0.0876(3) 0.2192(2) 0.60802(18) 0.0189(5) Uani 1 1 d . . .
C10 C 0.3310(3) 0.3585(2) 0.57728(19) 0.0209(6) Uani 1 1 d . . .
C11 C 0.5962(3) 0.3885(2) 0.71651(19) 0.0207(6) Uani 1 1 d . . .
C12 C 0.8676(3) 0.4427(3) 0.8293(2) 0.0291(6) Uani 1 1 d . . .
H12A H 0.8333 0.4721 0.8996 0.044 Uiso 1 1 calc R . .
H12B H 0.9760 0.5004 0.8395 0.044 Uiso 1 1 calc R . .
H12C H 0.8749 0.3406 0.8080 0.044 Uiso 1 1 calc R . .
C13 C 0.3103(3) 0.6693(3) 0.9576(2) 0.0298(6) Uani 1 1 d . . .
H13 H 0.3792 0.6410 1.0118 0.036 Uiso 1 1 calc R . .
C14 C 0.3076(3) 0.6116(3) 0.8457(2) 0.0314(6) Uani 1 1 d . . .
H14 H 0.3754 0.5438 0.8230 0.038 Uiso 1 1 calc R . .
C15 C 0.2074(3) 0.6516(3) 0.7668(2) 0.0329(7) Uani 1 1 d . . .
H15 H 0.2050 0.6104 0.6898 0.039 Uiso 1 1 calc R . .
C16 C 0.1101(3) 0.7516(3) 0.7996(2) 0.0326(6) Uani 1 1 d . . .
H16 H 0.0415 0.7801 0.7454 0.039 Uiso 1 1 calc R . .
C17 C 0.1134(3) 0.8100(3) 0.9121(2) 0.0316(6) Uani 1 1 d . . .
H17 H 0.0472 0.8790 0.9353 0.038 Uiso 1 1 calc R . .
C18 C 0.2128(3) 0.7680(3) 0.9903(2) 0.0290(6) Uani 1 1 d . . .
H18 H 0.2139 0.8074 1.0672 0.035 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
S1 C3 1.656(2) . ?
S2 C10 1.670(2) . ?
O1 C2 1.215(3) . ?
O2 C2 1.334(3) . ?
O2 C1 1.457(3) . ?
O3 C11 1.218(3) . ?
O4 C11 1.323(3) . ?
O4 C12 1.449(3) . ?
N1 C2 1.369(3) . ?
N1 C3 1.386(3) . ?
N2 C3 1.338(3) . ?
N2 C4 1.436(3) . ?
N3 C10 1.346(3) . ?
N3 C9 1.413(3) . ?
N4 C11 1.381(3) . ?
N4 C10 1.385(3) . ?
C4 C5 1.383(3) . ?
C4 C9 1.400(3) . ?
C5 C6 1.381(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.392(3) . ?
C13 C18 1.374(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.375(4) . ?
C15 C16 1.382(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.377(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
C2 O2 C1 114.55(17) . . ?
C11 O4 C12 115.58(17) . . ?
C2 N1 C3 127.3(2) . . ?
C3 N2 C4 122.71(19) . . ?
C10 N3 C9 130.6(2) . . ?
C11 N4 C10 128.3(2) . . ?
O1 C2 O2 124.1(2) . . ?
O1 C2 N1 125.4(2) . . ?
O2 C2 N1 110.5(2) . . ?
N2 C3 N1 115.9(2) . . ?
N2 C3 S1 124.35(17) . . ?
N1 C3 S1 119.75(17) . . ?
C5 C4 C9 120.5(2) . . ?
C5 C4 N2 120.11(19) . . ?
C9 C4 N2 119.43(19) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 C7 119.9(2) . . ?
C6 C7 C8 120.7(2) . . ?
C7 C8 C9 119.9(2) . . ?
C8 C9 C4 119.0(2) . . ?
C8 C9 N3 125.5(2) . . ?
C4 C9 N3 115.4(2) . . ?
N3 C10 N4 114.3(2) . . ?
N3 C10 S2 127.29(18) . . ?
N4 C10 S2 118.37(17) . . ?
O3 C11 O4 125.5(2) . . ?
O3 C11 N4 125.0(2) . . ?
O4 C11 N4 109.47(19) . . ?
C18 C13 C14 119.6(2) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 C16 120.0(2) . . ?
C15 C16 C17 119.5(2) . . ?
C18 C17 C16 120.0(2) . . ?
C13 C18 C17 120.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 1.4(3) . . . . ?
C1 O2 C2 N1 -177.97(18) . . . . ?
C3 N1 C2 O1 8.1(4) . . . . ?
C3 N1 C2 O2 -172.50(19) . . . . ?
C4 N2 C3 N1 177.19(18) . . . . ?
C4 N2 C3 S1 -2.2(3) . . . . ?
C2 N1 C3 N2 2.9(3) . . . . ?
C2 N1 C3 S1 -177.71(17) . . . . ?
C3 N2 C4 C5 -83.2(3) . . . . ?
C3 N2 C4 C9 98.1(2) . . . . ?
C9 C4 C5 C6 -1.3(3) . . . . ?
N2 C4 C5 C6 180.0(2) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C4 -1.3(3) . . . . ?
C7 C8 C9 N3 -177.7(2) . . . . ?
C5 C4 C9 C8 1.9(3) . . . . ?
N2 C4 C9 C8 -179.35(19) . . . . ?
C5 C4 C9 N3 178.76(19) . . . . ?
N2 C4 C9 N3 -2.5(3) . . . . ?
C10 N3 C9 C8 -25.4(4) . . . . ?
C10 N3 C9 C4 158.0(2) . . . . ?
C9 N3 C10 N4 177.4(2) . . . . ?
C9 N3 C10 S2 -2.1(3) . . . . ?
C11 N4 C10 N3 3.9(3) . . . . ?
C11 N4 C10 S2 -176.55(17) . . . . ?
C12 O4 C11 O3 5.8(3) . . . . ?
C12 O4 C11 N4 -175.03(18) . . . . ?
C10 N4 C11 O3 3.3(4) . . . . ?
C10 N4 C11 O4 -175.9(2) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C14 C13 C18 C17 -0.4(4) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.863(16) 2.01(2) 2.668(2) 132(2) .
N3 H3 O3 0.888(16) 1.894(19) 2.657(2) 143(2) .
N1 H1 O2 0.881(16) 2.407(18) 3.263(2) 164(2) 2_657
N4 H4 S2 0.881(16) 2.476(17) 3.3420(19) 167(2) 2_666

_diffrn_measured_fraction_theta_max 0.898
_diffrn_reflns_theta_full        58.06
_diffrn_measured_fraction_theta_full 0.898
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.079


