# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 'p-xylylenebis(thioacetic) acid'
;
_chemical_name_common            ?
_chemical_melting_point          149-150\%C
_chemical_formula_moiety         'C12 H14 O4 S2'
_chemical_formula_sum            'C12 H14 O4 S2'
_chemical_formula_weight         286.35

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

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

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

_cell_length_a                   9.4633(4)
_cell_length_b                   12.6496(4)
_cell_length_c                   10.8834(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.267(4)
_cell_angle_gamma                90.00
_cell_volume                     1262.64(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2079
_cell_measurement_theta_min      2.7376
_cell_measurement_theta_max      30.0380

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_min  0.98967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2837
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1452
_reflns_number_gt                1358
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.8462P] 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         1452
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.006

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33553(14) 0.41695(11) 0.91180(12) 0.0126(3) Uani 1 1 d . . .
C2 C 0.20382(15) 0.35596(11) 0.84183(13) 0.0133(3) Uani 1 1 d . . .
C3 C 0.26782(15) 0.38329(11) 0.60428(13) 0.0131(3) Uani 1 1 d . . .
C4 C 0.12959(14) 0.44347(10) 0.54960(12) 0.0118(3) Uani 1 1 d . . .
C5 C 0.10364(15) 0.54004(11) 0.60263(12) 0.0127(3) Uani 1 1 d . . .
C6 C -0.02452(15) 0.59588(11) 0.55354(13) 0.0128(3) Uani 1 1 d . . .
O1 O 0.40995(11) 0.37045(8) 1.01658(9) 0.0161(2) Uani 1 1 d . . .
O2 O 0.37040(11) 0.50124(8) 0.87296(9) 0.0154(2) Uani 1 1 d . . .
S1 S 0.24670(4) 0.27926(3) 0.71482(3) 0.01421(14) Uani 1 1 d . . .
H3A H 0.3465(19) 0.4295(14) 0.6459(16) 0.016(4) Uiso 1 1 d . . .
H6 H -0.0424(18) 0.6572(13) 0.5913(16) 0.012(4) Uiso 1 1 d . . .
H5 H 0.1712(19) 0.5670(14) 0.6721(17) 0.018(4) Uiso 1 1 d . . .
H3B H 0.2968(19) 0.3440(14) 0.5377(17) 0.019(4) Uiso 1 1 d . . .
H2A H 0.1257(19) 0.4067(13) 0.8095(15) 0.013(4) Uiso 1 1 d . . .
H2B H 0.1766(19) 0.3053(15) 0.8974(17) 0.017(4) Uiso 1 1 d . . .
H1O H 0.478(2) 0.4102(17) 1.0508(19) 0.034(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0125(6) 0.0145(6) 0.0111(6) -0.0021(5) 0.0036(5) 0.0019(5)
C2 0.0125(6) 0.0152(6) 0.0124(6) 0.0001(5) 0.0033(5) -0.0013(5)
C3 0.0134(6) 0.0133(6) 0.0126(6) 0.0008(5) 0.0033(5) 0.0021(5)
C4 0.0125(6) 0.0124(6) 0.0114(6) 0.0026(5) 0.0046(5) 0.0001(5)
C5 0.0140(6) 0.0126(6) 0.0107(6) 0.0001(5) 0.0015(5) -0.0017(5)
C6 0.0168(7) 0.0099(6) 0.0125(6) -0.0008(5) 0.0049(5) 0.0007(5)
O1 0.0152(5) 0.0164(5) 0.0138(5) 0.0021(4) -0.0018(4) -0.0026(4)
O2 0.0158(5) 0.0144(5) 0.0143(5) 0.0003(4) 0.0009(4) -0.0020(4)
S1 0.0190(2) 0.0096(2) 0.0131(2) 0.00044(11) 0.00197(14) 0.00161(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.2220(17) . ?
C1 O1 1.3216(16) . ?
C1 C2 1.5035(18) . ?
C2 S1 1.8147(14) . ?
C2 H2A 0.977(17) . ?
C2 H2B 0.959(18) . ?
C3 C4 1.5038(18) . ?
C3 S1 1.8268(14) . ?
C3 H3A 0.967(18) . ?
C3 H3B 0.972(18) . ?
C4 C6 1.3951(19) 5_566 ?
C4 C5 1.3985(18) . ?
C5 C6 1.391(2) . ?
C5 H5 0.926(18) . ?
C6 H6 0.913(17) . ?
O1 H1O 0.83(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 123.70(13) . . ?
O2 C1 C2 122.23(12) . . ?
O1 C1 C2 114.06(11) . . ?
C1 C2 S1 110.31(9) . . ?
C1 C2 H2A 107.7(10) . . ?
S1 C2 H2A 111.6(9) . . ?
C1 C2 H2B 110.0(11) . . ?
S1 C2 H2B 105.6(11) . . ?
H2A C2 H2B 111.7(14) . . ?
C4 C3 S1 113.55(9) . . ?
C4 C3 H3A 112.0(10) . . ?
S1 C3 H3A 108.9(10) . . ?
C4 C3 H3B 109.9(10) . . ?
S1 C3 H3B 102.7(10) . . ?
H3A C3 H3B 109.4(14) . . ?
C6 C4 C5 118.75(12) 5_566 . ?
C6 C4 C3 121.05(12) 5_566 . ?
C5 C4 C3 120.20(12) . . ?
C6 C5 C4 120.67(12) . . ?
C6 C5 H5 119.2(11) . . ?
C4 C5 H5 120.1(11) . . ?
C5 C6 C4 120.58(13) . 5_566 ?
C5 C6 H6 120.0(11) . . ?
C4 C6 H6 119.4(10) 5_566 . ?
C1 O1 H1O 107.9(14) . . ?
C2 S1 C3 101.41(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 S1 81.87(14) . . . . ?
O1 C1 C2 S1 -97.13(12) . . . . ?
S1 C3 C4 C6 -82.30(14) . . . 5_566 ?
S1 C3 C4 C5 97.08(13) . . . . ?
C6 C4 C5 C6 0.0(2) 5_566 . . . ?
C3 C4 C5 C6 -179.38(12) . . . . ?
C4 C5 C6 C4 0.0(2) . . . 5_566 ?
C1 C2 S1 C3 -69.88(10) . . . . ?
C4 C3 S1 C2 -64.69(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 1014647'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_II

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          152\%C
_chemical_formula_moiety         'C12 H14 O4 S2, 2(C6 H9 N3)'
_chemical_formula_sum            'C24 H32 N6 O4 S2'
_chemical_formula_weight         532.68

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

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

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

_cell_length_a                   17.6366(18)
_cell_length_b                   4.8355(5)
_cell_length_c                   15.5930(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.069(10)
_cell_angle_gamma                90.00
_cell_volume                     1322.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4443
_cell_measurement_theta_min      2.5419
_cell_measurement_theta_max      29.9491

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_min  0.30796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8987
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3027
_reflns_number_gt                2354
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1077P)²+0.0552P] 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         3027
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24551(11) 0.2524(4) 0.58623(13) 0.0245(4) Uani 1 1 d . . .
C2 C 0.29917(12) 0.0223(4) 0.61995(13) 0.0258(4) Uani 1 1 d . . .
H2A H 0.3214 -0.0624 0.5720 0.031 Uiso 1 1 calc R . .
H2B H 0.2705 -0.1186 0.6469 0.031 Uiso 1 1 calc R . .
C3 C 0.43417(13) 0.3416(4) 0.62824(14) 0.0287(5) Uani 1 1 d . . .
H3A H 0.4033 0.4852 0.5984 0.034 Uiso 1 1 calc R . .
H3B H 0.4753 0.4315 0.6641 0.034 Uiso 1 1 calc R . .
C4 C 0.46807(11) 0.1652(4) 0.56219(14) 0.0248(4) Uani 1 1 d . . .
C5 C 0.44170(12) 0.1845(4) 0.47388(14) 0.0278(5) Uani 1 1 d . . .
H5 H 0.4026 0.3070 0.4559 0.033 Uiso 1 1 calc R . .
C6 C 0.47357(11) 0.0223(5) 0.41333(14) 0.0277(5) Uani 1 1 d . . .
H6 H 0.4556 0.0393 0.3553 0.033 Uiso 1 1 calc R . .
C7 C 0.11302(11) 0.8566(4) 0.46685(13) 0.0241(4) Uani 1 1 d . . .
C8 C 0.10001(12) 1.1608(4) 0.35263(14) 0.0263(4) Uani 1 1 d . . .
C9 C 0.16951(12) 1.0696(4) 0.32630(14) 0.0273(5) Uani 1 1 d . . .
H9 H 0.1879 1.1412 0.2771 0.033 Uiso 1 1 calc R . .
C10 C 0.20970(12) 0.8706(4) 0.37563(13) 0.0243(4) Uani 1 1 d . . .
C11 C 0.05479(15) 1.3821(5) 0.30311(17) 0.0332(5) Uani 1 1 d . . .
C12 C 0.28467(13) 0.7573(5) 0.35426(16) 0.0298(5) Uani 1 1 d . . .
O1 O 0.26570(8) 0.3702(3) 0.51653(10) 0.0276(4) Uani 1 1 d . . .
O2 O 0.18982(9) 0.3183(4) 0.62231(10) 0.0353(4) Uani 1 1 d . . .
N1 N 0.18157(9) 0.7625(4) 0.44631(11) 0.0230(4) Uani 1 1 d . . .
N2 N 0.08425(10) 0.7427(4) 0.53451(12) 0.0299(4) Uani 1 1 d . . .
N3 N 0.07162(10) 1.0558(4) 0.42184(11) 0.0264(4) Uani 1 1 d . . .
S1 S 0.37518(3) 0.15026(11) 0.69804(3) 0.02698(19) Uani 1 1 d . . .
H21 H 0.1085 0.6123 0.5616 0.040 Uiso 1 1 d . . .
H1O H 0.2370 0.5181 0.4991 0.040 Uiso 1 1 d . . .
H22 H 0.0475 0.8048 0.5531 0.040 Uiso 1 1 d . . .
H11A H 0.001(2) 1.358(6) 0.306(2) 0.060(10) Uiso 1 1 d . . .
H11B H 0.0636(19) 1.556(8) 0.323(2) 0.060(9) Uiso 1 1 d . . .
H11C H 0.061(2) 1.377(7) 0.237(2) 0.071(11) Uiso 1 1 d . . .
H12A H 0.3197(18) 0.770(7) 0.404(2) 0.049(8) Uiso 1 1 d . . .
H12B H 0.2803(16) 0.569(6) 0.3403(17) 0.039(7) Uiso 1 1 d . . .
H12C H 0.3014(16) 0.851(5) 0.3008(18) 0.037(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0204(9) 0.0292(11) 0.0248(10) -0.0031(8) 0.0060(8) -0.0023(8)
C2 0.0233(10) 0.0283(11) 0.0264(10) 0.0004(8) 0.0065(8) -0.0017(8)
C3 0.0246(10) 0.0308(11) 0.0319(12) -0.0035(8) 0.0095(8) -0.0011(8)
C4 0.0190(9) 0.0259(10) 0.0308(11) 0.0007(8) 0.0091(8) -0.0040(8)
C5 0.0208(10) 0.0311(11) 0.0328(12) 0.0060(8) 0.0083(8) 0.0046(8)
C6 0.0204(9) 0.0367(12) 0.0269(10) 0.0012(8) 0.0065(8) -0.0002(8)
C7 0.0203(9) 0.0252(10) 0.0272(11) -0.0033(7) 0.0042(8) -0.0003(8)
C8 0.0262(10) 0.0251(10) 0.0272(10) -0.0009(8) 0.0004(8) -0.0030(8)
C9 0.0281(11) 0.0289(11) 0.0255(10) 0.0005(8) 0.0057(8) -0.0043(9)
C10 0.0236(10) 0.0250(11) 0.0250(10) -0.0035(7) 0.0058(8) -0.0054(8)
C11 0.0319(12) 0.0280(13) 0.0382(14) 0.0035(9) -0.0031(10) -0.0001(9)
C12 0.0260(11) 0.0346(13) 0.0305(12) 0.0001(9) 0.0113(9) -0.0004(9)
O1 0.0253(8) 0.0305(8) 0.0288(8) 0.0058(6) 0.0108(6) 0.0056(6)
O2 0.0291(8) 0.0471(10) 0.0321(9) 0.0063(7) 0.0142(7) 0.0110(7)
N1 0.0189(8) 0.0267(9) 0.0241(9) -0.0002(7) 0.0060(6) -0.0002(7)
N2 0.0227(9) 0.0348(10) 0.0341(10) 0.0065(8) 0.0122(8) 0.0074(8)
N3 0.0237(9) 0.0259(9) 0.0297(9) 0.0001(7) 0.0036(7) 0.0010(7)
S1 0.0212(3) 0.0363(3) 0.0244(3) -0.00130(19) 0.00654(19) -0.0002(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.225(3) . ?
C1 O1 1.310(3) . ?
C1 C2 1.518(3) . ?
C2 S1 1.821(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.509(3) . ?
C3 S1 1.834(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.394(3) 3_656 ?
C4 C5 1.409(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C4 1.394(3) 3_656 ?
C6 H6 0.9300 . ?
C7 N2 1.337(3) . ?
C7 N3 1.359(3) . ?
C7 N1 1.361(3) . ?
C8 N3 1.337(3) . ?
C8 C9 1.404(3) . ?
C8 C11 1.499(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 N1 1.360(3) . ?
C10 C12 1.501(3) . ?
C11 H11A 0.96(4) . ?
C11 H11B 0.91(4) . ?
C11 H11C 1.05(4) . ?
C12 H12A 0.94(3) . ?
C12 H12B 0.94(3) . ?
C12 H12C 1.02(3) . ?
O1 H1O 0.9013 . ?
N2 H21 0.8489 . ?
N2 H22 0.7962 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 124.73(19) . . ?
O2 C1 C2 122.18(19) . . ?
O1 C1 C2 113.08(17) . . ?
C1 C2 S1 111.73(15) . . ?
C1 C2 H2A 109.3 . . ?
S1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
S1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 S1 114.23(15) . . ?
C4 C3 H3A 108.7 . . ?
S1 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
S1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C6 C4 C5 117.93(19) 3_656 . ?
C6 C4 C3 121.01(19) 3_656 . ?
C5 C4 C3 121.05(19) . . ?
C6 C5 C4 120.70(19) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C4 121.36(19) . 3_656 ?
C5 C6 H6 119.3 . . ?
C4 C6 H6 119.3 3_656 . ?
N2 C7 N3 118.14(18) . . ?
N2 C7 N1 117.96(18) . . ?
N3 C7 N1 123.89(19) . . ?
N3 C8 C9 122.01(19) . . ?
N3 C8 C11 117.5(2) . . ?
C9 C8 C11 120.4(2) . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
N1 C10 C9 120.64(19) . . ?
N1 C10 C12 116.43(18) . . ?
C9 C10 C12 122.9(2) . . ?
C8 C11 H11A 111.4(19) . . ?
C8 C11 H11B 115(2) . . ?
H11A C11 H11B 103(3) . . ?
C8 C11 H11C 112(2) . . ?
H11A C11 H11C 105(3) . . ?
H11B C11 H11C 109(3) . . ?
C10 C12 H12A 108.3(19) . . ?
C10 C12 H12B 110.7(18) . . ?
H12A C12 H12B 106(3) . . ?
C10 C12 H12C 111.0(16) . . ?
H12A C12 H12C 115(3) . . ?
H12B C12 H12C 105(2) . . ?
C1 O1 H1O 113.7 . . ?
C10 N1 C7 118.14(17) . . ?
C7 N2 H21 119.0 . . ?
C7 N2 H22 121.6 . . ?
H21 N2 H22 119.1 . . ?
C8 N3 C7 117.35(18) . . ?
C2 S1 C3 101.44(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 S1 -88.3(2) . . . . ?
O1 C1 C2 S1 91.09(19) . . . . ?
S1 C3 C4 C6 -71.1(2) . . . 3_656 ?
S1 C3 C4 C5 108.8(2) . . . . ?
C6 C4 C5 C6 -0.5(3) 3_656 . . . ?
C3 C4 C5 C6 179.60(19) . . . . ?
C4 C5 C6 C4 0.5(3) . . . 3_656 ?
N3 C8 C9 C10 -1.7(3) . . . . ?
C11 C8 C9 C10 178.3(2) . . . . ?
C8 C9 C10 N1 1.5(3) . . . . ?
C8 C9 C10 C12 -179.8(2) . . . . ?
C9 C10 N1 C7 -0.1(3) . . . . ?
C12 C10 N1 C7 -178.84(19) . . . . ?
N2 C7 N1 C10 177.60(18) . . . . ?
N3 C7 N1 C10 -1.3(3) . . . . ?
C9 C8 N3 C7 0.4(3) . . . . ?
C11 C8 N3 C7 -179.58(19) . . . . ?
N2 C7 N3 C8 -177.77(19) . . . . ?
N1 C7 N3 C8 1.1(3) . . . . ?
C1 C2 S1 C3 -72.30(16) . . . . ?
C4 C3 S1 C2 -62.47(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 1014648'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_IV

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          150\%C
_chemical_formula_moiety         'C12 H14 O4 S2, 2(C6 H9 N3), 2(H2 O)'
_chemical_formula_sum            'C24 H36 N6 O6 S2'
_chemical_formula_weight         568.71

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

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

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

_cell_length_a                   20.968(3)
_cell_length_b                   4.7107(5)
_cell_length_c                   14.4013(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.307(10)
_cell_angle_gamma                90.00
_cell_volume                     1416.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1690
_cell_measurement_theta_min      2.5131
_cell_measurement_theta_max      30.4085

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_min  0.70029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9304
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3235
_reflns_number_gt                2308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0573P)²+0.1729P] 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         3235
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28122(14) 0.2927(6) 0.83140(19) 0.0184(6) Uani 1 1 d . . .
C2 C 0.33428(14) 0.5027(6) 0.81845(19) 0.0203(6) Uani 1 1 d . . .
H2A H 0.3520 0.5724 0.8788 0.024 Uiso 1 1 calc R . .
H2B H 0.3171 0.6633 0.7822 0.024 Uiso 1 1 calc R . .
C3 C 0.43969(15) 0.1324(6) 0.8541(2) 0.0241(7) Uani 1 1 d . . .
H3A H 0.4096 0.0074 0.8810 0.029 Uiso 1 1 calc R . .
H3B H 0.4720 0.0150 0.8290 0.029 Uiso 1 1 calc R . .
C4 C 0.47154(14) 0.3194(5) 0.93013(18) 0.0174(6) Uani 1 1 d . . .
C5 C 0.52987(14) 0.4483(6) 0.91959(19) 0.0208(6) Uani 1 1 d . . .
H5 H 0.5505 0.4125 0.8663 0.025 Uiso 1 1 calc R . .
C6 C 0.44182(14) 0.3689(6) 1.01229(19) 0.0195(6) Uani 1 1 d . . .
H6 H 0.4033 0.2799 1.0212 0.023 Uiso 1 1 calc R . .
C7 C 0.14924(14) 0.7872(6) 0.3935(2) 0.0191(6) Uani 1 1 d . . .
C8 C 0.12029(14) 1.1074(6) 0.5030(2) 0.0204(6) Uani 1 1 d . . .
C9 C 0.17703(15) 1.0528(6) 0.55856(19) 0.0209(6) Uani 1 1 d . . .
H9 H 0.1864 1.1461 0.6151 0.025 Uiso 1 1 calc R . .
C10 C 0.21909(14) 0.8551(6) 0.52692(19) 0.0188(6) Uani 1 1 d . . .
C11 C 0.07169(15) 1.3132(6) 0.5335(2) 0.0284(7) Uani 1 1 d . . .
H11A H 0.0372 1.2105 0.5575 0.043 Uiso 1 1 calc R . .
H11B H 0.0552 1.4260 0.4812 0.043 Uiso 1 1 calc R . .
H11C H 0.0916 1.4348 0.5812 0.043 Uiso 1 1 calc R . .
C12 C 0.28099(15) 0.7786(6) 0.5811(2) 0.0244(7) Uani 1 1 d . . .
H12A H 0.2772 0.5947 0.6088 0.037 Uiso 1 1 calc R . .
H12B H 0.2910 0.9169 0.6292 0.037 Uiso 1 1 calc R . .
H12C H 0.3145 0.7749 0.5400 0.037 Uiso 1 1 calc R . .
O1 O 0.28924(10) 0.1556(4) 0.91069(13) 0.0220(5) Uani 1 1 d . . .
O2 O 0.23649(10) 0.2572(4) 0.77192(14) 0.0269(5) Uani 1 1 d . . .
O1W O -0.00402(12) 1.1676(5) 0.30013(18) 0.0299(6) Uani 1 1 d . . .
S1 S 0.39726(4) 0.33509(16) 0.75896(5) 0.0234(2) Uani 1 1 d . . .
N1 N 0.20521(11) 0.7232(5) 0.44381(15) 0.0183(5) Uani 1 1 d . . .
N2 N 0.13633(13) 0.6526(6) 0.31165(17) 0.0238(6) Uani 1 1 d . . .
N3 N 0.10595(11) 0.9791(5) 0.42028(16) 0.0210(5) Uani 1 1 d . . .
H1O H 0.2574 0.0060 0.9196 0.031 Uiso 1 1 d . . .
H1W H 0.0304(18) 1.137(7) 0.339(2) 0.035(10) Uiso 1 1 d . . .
H2W H 0.007(2) 1.307(8) 0.280(3) 0.049(14) Uiso 1 1 d . . .
H21 H 0.1675(17) 0.538(7) 0.296(2) 0.031(9) Uiso 1 1 d . . .
H22 H 0.1002(19) 0.688(7) 0.275(2) 0.041(10) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0218(16) 0.0175(14) 0.0164(13) -0.0029(12) 0.0036(11) 0.0022(12)
C2 0.0263(17) 0.0208(15) 0.0133(13) -0.0004(12) -0.0012(11) -0.0014(12)
C3 0.0258(17) 0.0240(15) 0.0227(15) -0.0059(13) 0.0035(12) -0.0014(13)
C4 0.0219(15) 0.0151(13) 0.0149(13) 0.0011(12) 0.0003(11) 0.0004(11)
C5 0.0226(16) 0.0245(15) 0.0160(13) 0.0001(13) 0.0045(11) 0.0001(12)
C6 0.0202(16) 0.0199(14) 0.0187(14) 0.0024(12) 0.0036(11) -0.0011(11)
C7 0.0206(16) 0.0163(14) 0.0205(14) 0.0030(12) 0.0030(11) -0.0005(11)
C8 0.0225(16) 0.0171(14) 0.0223(15) 0.0051(12) 0.0068(12) -0.0007(12)
C9 0.0288(17) 0.0173(14) 0.0170(14) -0.0002(12) 0.0033(12) -0.0015(12)
C10 0.0238(16) 0.0168(14) 0.0161(13) 0.0033(12) 0.0025(11) -0.0014(12)
C11 0.0288(18) 0.0253(16) 0.0319(17) -0.0039(15) 0.0065(13) 0.0047(14)
C12 0.0258(17) 0.0275(16) 0.0190(14) -0.0006(13) -0.0024(12) -0.0002(13)
O1 0.0240(12) 0.0218(10) 0.0200(10) 0.0043(9) 0.0010(8) -0.0060(9)
O2 0.0263(13) 0.0351(12) 0.0187(10) 0.0035(10) -0.0013(9) -0.0075(10)
O1W 0.0263(14) 0.0243(12) 0.0372(14) 0.0015(12) -0.0070(10) -0.0019(10)
S1 0.0249(4) 0.0308(4) 0.0149(4) -0.0031(3) 0.0041(3) -0.0036(3)
N1 0.0202(13) 0.0188(12) 0.0158(11) -0.0010(10) 0.0013(9) -0.0006(10)
N2 0.0208(15) 0.0297(15) 0.0198(13) -0.0069(12) -0.0042(10) 0.0057(12)
N3 0.0205(14) 0.0193(12) 0.0231(12) 0.0006(11) 0.0020(10) 0.0021(10)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.222(3) . ?
C1 O1 1.309(3) . ?
C1 C2 1.513(4) . ?
C2 S1 1.820(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.512(4) . ?
C3 S1 1.832(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.387(4) . ?
C4 C6 1.407(4) . ?
C5 C6 1.396(4) 3_667 ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.344(4) . ?
C7 N1 1.355(3) . ?
C7 N3 1.362(4) . ?
C8 N3 1.345(3) . ?
C8 C9 1.395(4) . ?
C8 C11 1.501(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C10 N1 1.356(3) . ?
C10 C12 1.495(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O1 H1O 0.9873 . ?
O1W H1W 0.88(4) . ?
O1W H2W 0.76(4) . ?
N2 H21 0.89(3) . ?
N2 H22 0.90(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 124.9(3) . . ?
O2 C1 C2 121.9(2) . . ?
O1 C1 C2 113.2(2) . . ?
C1 C2 S1 110.38(19) . . ?
C1 C2 H2A 109.6 . . ?
S1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
S1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 S1 112.9(2) . . ?
C4 C3 H3A 109.0 . . ?
S1 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
S1 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C6 118.9(3) . . ?
C5 C4 C3 120.7(3) . . ?
C6 C4 C3 120.4(3) . . ?
C4 C5 C6 121.0(3) . 3_667 ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 3_667 . ?
C5 C6 C4 120.0(3) 3_667 . ?
C5 C6 H6 120.0 3_667 . ?
C4 C6 H6 120.0 . . ?
N2 C7 N1 117.3(3) . . ?
N2 C7 N3 118.4(3) . . ?
N1 C7 N3 124.3(3) . . ?
N3 C8 C9 122.3(3) . . ?
N3 C8 C11 116.5(3) . . ?
C9 C8 C11 121.2(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
N1 C10 C9 120.4(3) . . ?
N1 C10 C12 117.1(2) . . ?
C9 C10 C12 122.5(3) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 O1 H1O 115.6 . . ?
H1W O1W H2W 98(4) . . ?
C2 S1 C3 101.38(13) . . ?
C7 N1 C10 118.3(2) . . ?
C7 N2 H21 115(2) . . ?
C7 N2 H22 121(2) . . ?
H21 N2 H22 124(3) . . ?
C8 N3 C7 116.7(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
O2 C1 C2 S1 -87.8(3) . . . . ?
O1 C1 C2 S1 91.3(2) . . . . ?
S1 C3 C4 C5 -80.0(3) . . . . ?
S1 C3 C4 C6 98.9(3) . . . . ?
C6 C4 C5 C6 -1.8(4) . . . 3_667 ?
C3 C4 C5 C6 177.2(2) . . . 3_667 ?
C5 C4 C6 C5 1.8(4) . . . 3_667 ?
C3 C4 C6 C5 -177.2(2) . . . 3_667 ?
N3 C8 C9 C10 -1.1(4) . . . . ?
C11 C8 C9 C10 178.6(3) . . . . ?
C8 C9 C10 N1 0.8(4) . . . . ?
C8 C9 C10 C12 -179.5(3) . . . . ?
C1 C2 S1 C3 -78.1(2) . . . . ?
C4 C3 S1 C2 -65.1(2) . . . . ?
N2 C7 N1 C10 -179.6(2) . . . . ?
N3 C7 N1 C10 0.9(4) . . . . ?
C9 C10 N1 C7 -0.7(4) . . . . ?
C12 C10 N1 C7 179.6(3) . . . . ?
C9 C8 N3 C7 1.2(4) . . . . ?
C11 C8 N3 C7 -178.5(3) . . . . ?
N2 C7 N3 C8 179.4(2) . . . . ?
N1 C7 N3 C8 -1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.079
_database_code_depnum_ccdc_archive 'CCDC 1014649'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_III

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          156\%C
_chemical_formula_moiety         'C12 H14 O4 S2, C6 H9 N3'
_chemical_formula_sum            'C18 H23 N3 O4 S2'
_chemical_formula_weight         409.51

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Cmca
_symmetry_space_group_name_Hall  '-C 2bc 2 '

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

_cell_length_a                   32.932(7)
_cell_length_b                   7.9668(16)
_cell_length_c                   15.275(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4007.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3062
_cell_measurement_theta_min      2.5514
_cell_measurement_theta_max      30.3124

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_min  0.86775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.4221
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5299
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2326
_reflns_number_gt                1617
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL/PC (Sheldrick, 2008) and Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 and enCIFer (Allen et al., 2004)'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0451P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2326
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.903
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.10882(5) 0.0952(2) 0.60324(10) 0.0169(3) Uani 1 1 d . . .
C2 C 0.15099(5) 0.0468(2) 0.63130(11) 0.0172(3) Uani 1 1 d . . .
C3 C 0.18928(6) 0.3633(2) 0.62500(11) 0.0202(4) Uani 1 1 d . . .
C4 C 0.22078(5) 0.30531(18) 0.56066(10) 0.0163(3) Uani 1 1 d . . .
C5 C 0.26130(5) 0.2895(2) 0.58489(10) 0.0178(3) Uani 1 1 d . . .
C6 C 0.29016(5) 0.23520(19) 0.52510(10) 0.0178(4) Uani 1 1 d . . .
C7 C 0.0000 0.2655(3) 1.01044(14) 0.0165(5) Uani 1 2 d S . .
C8 C 0.03608(5) 0.1379(2) 0.89860(10) 0.0188(4) Uani 1 1 d . . .
C10 C 0.07666(6) 0.0930(3) 0.86133(12) 0.0262(4) Uani 1 1 d . . .
N1 N 0.03631(4) 0.22322(16) 0.97470(8) 0.0169(3) Uani 1 1 d . . .
C9 C 0.0000 0.0943(3) 0.85812(15) 0.0204(5) Uani 1 2 d S . .
N2 N 0.0000 0.3509(3) 1.08572(13) 0.0218(5) Uani 1 2 d S . .
O1 O 0.10798(4) 0.19595(13) 0.53445(7) 0.0200(3) Uani 1 1 d . . .
O2 O 0.07875(3) 0.04446(14) 0.64147(7) 0.0237(3) Uani 1 1 d . . .
S1 S 0.173649(12) 0.20196(5) 0.70312(3) 0.01988(12) Uani 1 1 d . . .
H9 H 0.0000 0.036(3) 0.8087(15) 0.009(6) Uiso 1 2 d S . .
H5 H 0.2696(5) 0.3197(19) 0.6428(11) 0.017(4) Uiso 1 1 d . . .
H3B H 0.1999(5) 0.454(2) 0.6631(11) 0.024(5) Uiso 1 1 d . . .
H2A H 0.1490(5) -0.054(2) 0.6642(10) 0.019(4) Uiso 1 1 d . . .
H6 H 0.3181(5) 0.2250(19) 0.5421(10) 0.015(4) Uiso 1 1 d . . .
H2B H 0.1683(5) 0.033(2) 0.5819(11) 0.018(4) Uiso 1 1 d . . .
H3A H 0.1654(5) 0.405(2) 0.5975(11) 0.023(5) Uiso 1 1 d . . .
H10C H 0.0747(7) 0.026(3) 0.8115(16) 0.052(6) Uiso 1 1 d . . .
H21 H -0.0235(5) 0.389(2) 1.1072(12) 0.030(5) Uiso 1 1 d . . .
H10B H 0.0912(7) 0.194(3) 0.8468(14) 0.050(7) Uiso 1 1 d . . .
H10A H 0.0930(8) 0.040(3) 0.9061(15) 0.061(7) Uiso 1 1 d . . .
H1O H 0.0790(9) 0.224(3) 0.5166(15) 0.072(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0183(9) 0.0182(8) 0.0142(8) -0.0028(6) -0.0019(6) -0.0005(7)
C2 0.0171(9) 0.0181(8) 0.0164(8) 0.0012(7) -0.0001(7) -0.0002(7)
C3 0.0198(9) 0.0190(9) 0.0219(8) -0.0029(7) 0.0015(7) -0.0001(8)
C4 0.0179(8) 0.0112(7) 0.0196(8) 0.0009(6) 0.0020(6) -0.0020(7)
C5 0.0192(8) 0.0185(8) 0.0156(8) -0.0012(7) -0.0021(6) -0.0028(7)
C6 0.0138(8) 0.0167(8) 0.0230(8) 0.0009(6) -0.0037(6) -0.0010(7)
C7 0.0157(11) 0.0194(11) 0.0145(10) 0.0021(9) 0.000 0.000
C8 0.0214(9) 0.0184(8) 0.0167(8) 0.0012(6) 0.0019(7) 0.0006(7)
C10 0.0218(10) 0.0344(11) 0.0224(9) -0.0065(9) 0.0032(8) 0.0025(9)
N1 0.0145(7) 0.0205(7) 0.0157(7) -0.0015(5) 0.0008(5) 0.0001(6)
C9 0.0230(13) 0.0236(13) 0.0146(11) -0.0052(10) 0.000 0.000
N2 0.0117(10) 0.0332(12) 0.0203(10) -0.0096(9) 0.000 0.000
O1 0.0154(6) 0.0252(6) 0.0196(6) 0.0065(5) -0.0010(5) -0.0002(5)
O2 0.0162(6) 0.0338(7) 0.0212(6) 0.0069(5) 0.0009(5) -0.0022(5)
S1 0.0188(2) 0.0263(2) 0.01461(19) -0.00226(17) -0.00028(16) -0.00275(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.2185(19) . ?
C1 O1 1.3227(18) . ?
C1 C2 1.504(2) . ?
C2 S1 1.8135(16) . ?
C2 H2A 0.947(16) . ?
C2 H2B 0.953(17) . ?
C3 C4 1.502(2) . ?
C3 S1 1.8279(17) . ?
C3 H3B 0.991(17) . ?
C3 H3A 0.951(18) . ?
C4 C5 1.390(2) . ?
C4 C6 1.396(2) 13_556 ?
C5 C6 1.387(2) . ?
C5 H5 0.957(17) . ?
C6 H6 0.958(17) . ?
C7 N2 1.336(3) . ?
C7 N1 1.3568(16) . ?
C8 N1 1.3468(19) . ?
C8 C9 1.384(2) . ?
C8 C10 1.496(2) . ?
C10 H10C 0.93(2) . ?
C10 H10B 0.96(2) . ?
C10 H10A 0.97(2) . ?
C9 H9 0.89(2) . ?
N2 H21 0.896(17) . ?
O1 H1O 1.02(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
O2 C1 O1 124.39(15) . . ?
O2 C1 C2 121.94(15) . . ?
O1 C1 C2 113.67(14) . . ?
C1 C2 S1 112.20(11) . . ?
C1 C2 H2A 107.7(10) . . ?
S1 C2 H2A 106.5(10) . . ?
C1 C2 H2B 110.9(10) . . ?
S1 C2 H2B 108.3(10) . . ?
H2A C2 H2B 111.2(14) . . ?
C4 C3 S1 113.92(12) . . ?
C4 C3 H3B 111.4(10) . . ?
S1 C3 H3B 103.2(9) . . ?
C4 C3 H3A 112.9(10) . . ?
S1 C3 H3A 107.4(11) . . ?
H3B C3 H3A 107.4(15) . . ?
C5 C4 C6 118.45(15) . 13_556 ?
C5 C4 C3 121.10(15) . . ?
C6 C4 C3 120.44(15) 13_556 . ?
C6 C5 C4 120.69(15) . . ?
C6 C5 H5 119.3(10) . . ?
C4 C5 H5 119.9(10) . . ?
C5 C6 C4 120.85(15) . 13_556 ?
C5 C6 H6 120.4(10) . . ?
C4 C6 H6 118.8(10) 13_556 . ?
N2 C7 N1 118.20(10) . 12 ?
N2 C7 N1 118.20(10) . . ?
N1 C7 N1 123.6(2) 12 . ?
N1 C8 C9 121.14(16) . . ?
N1 C8 C10 116.37(15) . . ?
C9 C8 C10 122.49(16) . . ?
C8 C10 H10C 112.8(14) . . ?
C8 C10 H10B 109.6(13) . . ?
H10C C10 H10B 108.9(18) . . ?
C8 C10 H10A 109.4(14) . . ?
H10C C10 H10A 111.3(18) . . ?
H10B C10 H10A 104.6(18) . . ?
C8 N1 C7 117.88(15) . . ?
C8 C9 C8 118.3(2) . 12 ?
C8 C9 H9 120.80(11) . . ?
C8 C9 H9 120.80(12) 12 . ?
C7 N2 H21 119.3(12) . . ?
C1 O1 H1O 111.4(13) . . ?
C2 S1 C3 101.55(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
O2 C1 C2 S1 -95.16(16) . . . . ?
O1 C1 C2 S1 84.84(15) . . . . ?
S1 C3 C4 C5 -76.96(17) . . . . ?
S1 C3 C4 C6 102.60(15) . . . 13_556 ?
C6 C4 C5 C6 0.2(2) 13_556 . . . ?
C3 C4 C5 C6 179.74(14) . . . . ?
C4 C5 C6 C4 -0.2(3) . . . 13_556 ?
C9 C8 N1 C7 -0.1(2) . . . . ?
C10 C8 N1 C7 -179.81(16) . . . . ?
N2 C7 N1 C8 -179.67(17) . . . . ?
N1 C7 N1 C8 1.5(3) 12 . . . ?
N1 C8 C9 C8 -1.2(3) . . . 12 ?
C10 C8 C9 C8 178.50(14) . . . 12 ?
C1 C2 S1 C3 -78.43(13) . . . . ?
C4 C3 S1 C2 -63.30(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 1014650'
