# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_jcm_thf

#=========================================================================
# Data for compound 2a (local labelling jcm-thf)
#========================================================================= 

# start Validation Reply Form
_vrf_RINTA01_jcm_thf             
;
PROBLEM: The value of Rint is greater than 0.18 
RESPONSE: The quality of the crystals was low, with very thin plate 
morphologies. However, the structure solution and refinement are 
unambiguous and fully consistent with the spectroscopic characterization 
of the compound. The final model is of a reasonable quality.
;

_vrf_PLAT020_jcm_thf             
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.208       
RESPONSE: Same as RINTA01
;

_vrf_PLAT149_jcm_thf             
;
PROBLEM: su on the   beta   Angle is Too Large ..........       0.30 Degree      
RESPONSE: Same as RINTA01
;

_vrf_PLAT340_jcm_thf             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0115 Ang.      
RESPONSE: This is also presumably due to the low quality data. See RINTA01.
;

_vrf_PLAT148_jcm_thf             
;
PROBLEM: su on the      a  - Axis is (Too) Large ........      0.050 Ang..      
RESPONSE: Same as RINTA01
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 Cl3 N O4 S'
_chemical_formula_sum            'C6 H10 Cl3 N O4 S'
_chemical_formula_weight         298.56

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   10.97(5)
_cell_length_b                   11.299(4)
_cell_length_c                   9.022(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4(3)
_cell_angle_gamma                90.00
_cell_volume                     1117(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    277
_cell_measurement_theta_min      7.8
_cell_measurement_theta_max      49.8

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    9.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4607
_exptl_absorpt_correction_T_max  0.8378
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'

_exptl_special_details           
; 
 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' 
;


_diffrn_ambient_temperature      93(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  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            28348
_diffrn_reflns_av_R_equivalents  0.2080
_diffrn_reflns_av_sigmaI/netI    0.1087
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.03
_diffrn_reflns_theta_max         66.58
_reflns_number_total             1940
_reflns_number_gt                1246
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r12'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1086P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1940
_refine_ls_number_parameters     139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2150
_refine_ls_wR_factor_gt          0.1991
_refine_ls_goodness_of_fit_ref   1.064
_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
N1 N 0.8871(4) 0.7633(4) 0.2724(5) 0.0414(12) Uani 1 1 d D . .
O1 O 0.7620(4) 0.7961(4) 0.0489(4) 0.0523(11) Uani 1 1 d . . .
O2 O 0.9716(4) 0.6167(4) 0.1036(5) 0.0565(12) Uani 1 1 d . . .
O3 O 1.0136(4) 0.6053(4) 0.3749(5) 0.0562(12) Uani 1 1 d . . .
O4 O 1.1044(4) 0.7523(4) 0.2182(4) 0.0494(11) Uani 1 1 d . . .
S1 S 0.99098(14) 0.67289(13) 0.24365(16) 0.0464(5) Uani 1 1 d . . .
Cl1 Cl 1.37097(17) 0.73651(15) 0.2773(3) 0.0813(7) Uani 1 1 d . . .
Cl2 Cl 1.34801(18) 0.94572(16) 0.4499(2) 0.0707(6) Uani 1 1 d . . .
Cl3 Cl 1.2710(2) 0.9468(2) 0.1429(2) 0.0856(8) Uani 1 1 d . . .
C1 C 0.6424(6) 0.7987(7) 0.0981(8) 0.065(2) Uani 1 1 d . . .
H1A H 0.6185 0.7198 0.1346 0.078 Uiso 1 1 calc R . .
H1B H 0.5844 0.8223 0.0164 0.078 Uiso 1 1 calc R . .
C2 C 0.6421(6) 0.8872(6) 0.2204(7) 0.0573(18) Uani 1 1 d . . .
H2A H 0.6238 0.8482 0.3152 0.069 Uiso 1 1 calc R . .
H2B H 0.5796 0.9487 0.1987 0.069 Uiso 1 1 calc R . .
C3 C 0.7691(6) 0.9422(5) 0.2304(7) 0.0487(16) Uani 1 1 d . . .
H3A H 0.7716 1.0178 0.1751 0.058 Uiso 1 1 calc R . .
H3B H 0.7971 0.9559 0.3348 0.058 Uiso 1 1 calc R . .
C4 C 0.8429(5) 0.8491(5) 0.1597(6) 0.0435(15) Uani 1 1 d . . .
H4 H 0.9138 0.8862 0.1112 0.052 Uiso 1 1 calc R . .
C5 C 1.1548(6) 0.8227(6) 0.3414(7) 0.0522(17) Uani 1 1 d . . .
H5A H 1.1584 0.7751 0.4336 0.063 Uiso 1 1 calc R . .
H5B H 1.1029 0.8929 0.3572 0.063 Uiso 1 1 calc R . .
C6 C 1.2799(6) 0.8603(5) 0.3029(6) 0.0490(16) Uani 1 1 d . . .
H1 H 0.852(6) 0.762(5) 0.360(4) 0.059 Uiso 1 1 d 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
N1 0.041(3) 0.049(3) 0.036(2) 0.006(2) 0.011(2) 0.005(2)
O1 0.047(3) 0.069(3) 0.041(2) -0.007(2) 0.007(2) 0.001(2)
O2 0.055(3) 0.061(2) 0.056(3) -0.012(2) 0.024(2) -0.002(2)
O3 0.059(3) 0.057(2) 0.054(3) 0.012(2) 0.026(2) 0.010(2)
O4 0.046(3) 0.063(2) 0.041(2) -0.0030(19) 0.0177(19) -0.0029(19)
S1 0.0437(10) 0.0529(8) 0.0439(9) -0.0006(7) 0.0169(7) 0.0028(7)
Cl1 0.0501(12) 0.0621(10) 0.1340(18) -0.0165(11) 0.0292(12) -0.0018(8)
Cl2 0.0735(13) 0.0835(12) 0.0564(10) -0.0187(9) 0.0174(9) -0.0152(9)
Cl3 0.0811(16) 0.1143(17) 0.0616(12) 0.0317(11) 0.0058(10) -0.0230(11)
C1 0.032(4) 0.087(5) 0.077(5) -0.030(4) 0.006(4) -0.002(3)
C2 0.049(4) 0.057(4) 0.067(4) -0.005(3) 0.023(3) -0.015(3)
C3 0.047(4) 0.053(3) 0.047(4) 0.003(3) 0.010(3) 0.004(3)
C4 0.036(4) 0.051(3) 0.044(3) -0.003(3) 0.010(3) -0.007(3)
C5 0.047(4) 0.065(4) 0.046(4) -0.003(3) 0.015(3) 0.000(3)
C6 0.046(4) 0.060(4) 0.042(3) -0.001(3) 0.012(3) -0.007(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.472(8) . ?
N1 S1 1.561(6) . ?
N1 H1 0.89(2) . ?
O1 C1 1.404(9) . ?
O1 C4 1.439(8) . ?
O2 S1 1.422(5) . ?
O3 S1 1.422(5) . ?
O4 C5 1.456(8) . ?
O4 S1 1.559(6) . ?
Cl1 C6 1.740(7) . ?
Cl2 C6 1.780(7) . ?
Cl3 C6 1.742(6) . ?
C1 C2 1.488(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.525(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.488(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 1.0000 . ?
C5 C6 1.492(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 S1 122.5(4) . . ?
C4 N1 H1 119(4) . . ?
S1 N1 H1 119(4) . . ?
C1 O1 C4 109.2(5) . . ?
C5 O4 S1 118.8(4) . . ?
O3 S1 O2 121.0(3) . . ?
O3 S1 O4 108.7(3) . . ?
O2 S1 O4 102.5(3) . . ?
O3 S1 N1 108.4(3) . . ?
O2 S1 N1 110.9(3) . . ?
O4 S1 N1 103.9(4) . . ?
O1 C1 C2 106.3(5) . . ?
O1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
O1 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C1 C2 C3 106.7(5) . . ?
C1 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C4 C3 C2 101.5(5) . . ?
C4 C3 H3A 111.5 . . ?
C2 C3 H3A 111.5 . . ?
C4 C3 H3B 111.5 . . ?
C2 C3 H3B 111.5 . . ?
H3A C3 H3B 109.3 . . ?
O1 C4 N1 112.4(5) . . ?
O1 C4 C3 105.2(6) . . ?
N1 C4 C3 109.8(5) . . ?
O1 C4 H4 109.8 . . ?
N1 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
O4 C5 C6 107.5(5) . . ?
O4 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 . . ?
O4 C5 H5B 110.2 . . ?
C6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C5 C6 Cl1 110.0(5) . . ?
C5 C6 Cl3 109.4(5) . . ?
Cl1 C6 Cl3 110.7(3) . . ?
C5 C6 Cl2 110.0(4) . . ?
Cl1 C6 Cl2 108.0(4) . . ?
Cl3 C6 Cl2 108.7(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
C5 O4 S1 O3 -49.1(5) . . . . ?
C5 O4 S1 O2 -178.2(4) . . . . ?
C5 O4 S1 N1 66.2(5) . . . . ?
C4 N1 S1 O3 178.7(4) . . . . ?
C4 N1 S1 O2 -46.3(5) . . . . ?
C4 N1 S1 O4 63.2(5) . . . . ?
C4 O1 C1 C2 17.3(8) . . . . ?
O1 C1 C2 C3 4.1(8) . . . . ?
C1 C2 C3 C4 -22.4(7) . . . . ?
C1 O1 C4 N1 87.0(6) . . . . ?
C1 O1 C4 C3 -32.4(6) . . . . ?
S1 N1 C4 O1 78.2(6) . . . . ?
S1 N1 C4 C3 -165.1(4) . . . . ?
C2 C3 C4 O1 32.5(6) . . . . ?
C2 C3 C4 N1 -88.7(6) . . . . ?
S1 O4 C5 C6 163.5(4) . . . . ?
O4 C5 C6 Cl1 -60.5(6) . . . . ?
O4 C5 C6 Cl3 61.3(6) . . . . ?
O4 C5 C6 Cl2 -179.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.139
_exptl_crystal_recrystallization_method 'Pentane/dichloromethane diffusion'
_database_code_depnum_ccdc_archive 'CCDC 1015066'
#######################################################################
#
#                 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_jcm318a

#=========================================================================
# Data for compound 2d (local labelling jcm318a)
#========================================================================= 


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 Cl N O3 S'
_chemical_formula_sum            'C10 H12 Cl N O3 S'
_chemical_formula_weight         261.72

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   7.9569(5)
_cell_length_b                   10.2188(4)
_cell_length_c                   14.1417(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.438(7)
_cell_angle_gamma                90.00
_cell_volume                     1140.19(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    6699
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9276
_exptl_absorpt_correction_T_max  0.9509
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'


_exptl_special_details           
; 
 'Rigaku R-AXIS RAPID, Rigaku R-AXIS RAPID imaging plate' 
;

_diffrn_ambient_temperature      93(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  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            10427
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_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         3.26
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2018
_reflns_number_gt                1309
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r12'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 0.49556(9) 0.11800(6) 0.63168(4) 0.0315(2) Uani 1 1 d . . .
Cl1 Cl 0.82827(10) 0.61455(6) 0.47755(5) 0.0432(2) Uani 1 1 d . . .
O1 O 0.8765(3) 0.09738(18) 0.72077(14) 0.0455(5) Uani 1 1 d . . .
C8 C 0.7397(3) 0.4747(2) 0.52120(19) 0.0312(6) Uani 1 1 d . . .
C5 C 0.5948(3) 0.2571(2) 0.58977(17) 0.0276(6) Uani 1 1 d . . .
C10 C 0.6496(4) 0.2535(3) 0.50087(19) 0.0348(7) Uani 1 1 d . . .
H10 H 0.6364 0.1760 0.4636 0.042 Uiso 1 1 calc R . .
C1 C 0.7677(4) -0.0106(3) 0.71878(19) 0.0408(8) Uani 1 1 d . . .
H1A H 0.7218 -0.0177 0.7811 0.049 Uiso 1 1 calc R . .
C6 C 0.6137(4) 0.3689(2) 0.64473(18) 0.0345(7) Uani 1 1 d . . .
H6 H 0.5779 0.3702 0.7063 0.041 Uiso 1 1 calc R . .
C2 C 0.8780(4) -0.1282(3) 0.7055(2) 0.0490(8) Uani 1 1 d . . .
H2A H 0.8099 -0.2018 0.6755 0.059 Uiso 1 1 calc R . .
H2B H 0.9400 -0.1576 0.7671 0.059 Uiso 1 1 calc R . .
C9 C 0.7237(4) 0.3632(2) 0.46613(18) 0.0360(7) Uani 1 1 d . . .
H9 H 0.7628 0.3615 0.4054 0.043 Uiso 1 1 calc R . .
C7 C 0.6852(4) 0.4792(3) 0.6093(2) 0.0384(7) Uani 1 1 d . . .
H7 H 0.6965 0.5575 0.6458 0.046 Uiso 1 1 calc R . .
C3 C 0.9985(5) -0.0752(3) 0.6400(2) 0.0553(9) Uani 1 1 d . . .
H3A H 1.1130 -0.1135 0.6557 0.066 Uiso 1 1 calc R . .
H3B H 0.9565 -0.0943 0.5724 0.066 Uiso 1 1 calc R . .
C4 C 1.0014(4) 0.0708(3) 0.6586(2) 0.0509(9) Uani 1 1 d . . .
H4A H 1.1150 0.0982 0.6890 0.061 Uiso 1 1 calc R . .
H4B H 0.9744 0.1194 0.5980 0.061 Uiso 1 1 calc R . .
N1 N 0.6268(3) -0.0029(2) 0.64078(15) 0.0327(6) Uani 1 1 d D . .
O2 O 0.3620(2) 0.08013(16) 0.55844(12) 0.0341(5) Uani 1 1 d . . .
O3 O 0.4551(2) 0.14755(18) 0.72493(12) 0.0403(5) Uani 1 1 d . . .
H1 H 0.645(4) -0.033(3) 0.5848(15) 0.048 Uiso 1 1 d 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
S1 0.0348(4) 0.0323(4) 0.0287(4) -0.0002(3) 0.0092(3) -0.0025(3)
Cl1 0.0450(5) 0.0284(4) 0.0561(5) 0.0047(3) 0.0059(4) -0.0052(3)
O1 0.0476(14) 0.0397(11) 0.0497(13) -0.0069(9) 0.0081(10) -0.0031(11)
C8 0.0260(16) 0.0274(14) 0.0399(16) 0.0032(12) 0.0032(12) -0.0008(12)
C5 0.0248(15) 0.0274(14) 0.0305(14) -0.0010(11) 0.0030(12) -0.0021(12)
C10 0.0440(19) 0.0309(15) 0.0312(15) -0.0037(11) 0.0113(13) -0.0039(14)
C1 0.048(2) 0.0414(18) 0.0340(16) 0.0030(13) 0.0098(14) -0.0007(15)
C6 0.0370(17) 0.0365(16) 0.0307(14) -0.0076(12) 0.0076(12) -0.0014(14)
C2 0.058(2) 0.0339(17) 0.0537(19) 0.0041(14) 0.0030(16) 0.0054(16)
C9 0.0438(19) 0.0339(16) 0.0314(15) -0.0020(12) 0.0084(13) -0.0036(14)
C7 0.0436(19) 0.0284(15) 0.0430(17) -0.0103(13) 0.0047(14) 0.0000(14)
C3 0.048(2) 0.061(2) 0.057(2) -0.0164(16) 0.0082(17) 0.0049(17)
C4 0.045(2) 0.055(2) 0.054(2) -0.0005(15) 0.0110(16) -0.0024(16)
N1 0.0395(15) 0.0318(13) 0.0269(12) -0.0002(10) 0.0049(11) 0.0034(11)
O2 0.0312(12) 0.0361(10) 0.0349(10) -0.0019(8) 0.0040(9) -0.0027(9)
O3 0.0467(13) 0.0473(12) 0.0298(10) -0.0032(8) 0.0156(9) -0.0032(10)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4297(18) . ?
S1 O2 1.4377(19) . ?
S1 N1 1.612(2) . ?
S1 C5 1.765(3) . ?
Cl1 C8 1.741(3) . ?
O1 C1 1.400(3) . ?
O1 C4 1.435(4) . ?
C8 C7 1.372(4) . ?
C8 C9 1.377(4) . ?
C5 C6 1.379(3) . ?
C5 C10 1.383(4) . ?
C10 C9 1.386(4) . ?
C10 H10 0.9500 . ?
C1 N1 1.470(4) . ?
C1 C2 1.514(4) . ?
C1 H1A 1.0000 . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C2 C3 1.517(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C9 H9 0.9500 . ?
C7 H7 0.9500 . ?
C3 C4 1.515(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N1 H1 0.876(17) . ?

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
O3 S1 O2 119.17(12) . . ?
O3 S1 N1 108.02(11) . . ?
O2 S1 N1 105.18(11) . . ?
O3 S1 C5 107.68(12) . . ?
O2 S1 C5 107.22(11) . . ?
N1 S1 C5 109.30(12) . . ?
C1 O1 C4 108.3(2) . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 Cl1 119.0(2) . . ?
C9 C8 Cl1 119.4(2) . . ?
C6 C5 C10 120.6(2) . . ?
C6 C5 S1 119.9(2) . . ?
C10 C5 S1 119.4(2) . . ?
C5 C10 C9 120.0(2) . . ?
C5 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O1 C1 N1 112.5(2) . . ?
O1 C1 C2 105.1(3) . . ?
N1 C1 C2 110.3(2) . . ?
O1 C1 H1A 109.6 . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C1 C2 C3 102.4(2) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C4 C3 C2 104.0(3) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O1 C4 C3 107.3(3) . . ?
O1 C4 H4A 110.3 . . ?
C3 C4 H4A 110.3 . . ?
O1 C4 H4B 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C1 N1 S1 121.60(18) . . ?
C1 N1 H1 118(2) . . ?
S1 N1 H1 111.8(19) . . ?

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
O3 S1 C5 C6 -2.4(3) . . . . ?
O2 S1 C5 C6 126.9(2) . . . . ?
N1 S1 C5 C6 -119.5(2) . . . . ?
O3 S1 C5 C10 179.0(2) . . . . ?
O2 S1 C5 C10 -51.6(2) . . . . ?
N1 S1 C5 C10 61.9(2) . . . . ?
C6 C5 C10 C9 -0.2(4) . . . . ?
S1 C5 C10 C9 178.3(2) . . . . ?
C4 O1 C1 N1 -86.8(3) . . . . ?
C4 O1 C1 C2 33.3(3) . . . . ?
C10 C5 C6 C7 1.3(4) . . . . ?
S1 C5 C6 C7 -177.3(2) . . . . ?
O1 C1 C2 C3 -36.0(3) . . . . ?
N1 C1 C2 C3 85.6(3) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
Cl1 C8 C9 C10 -178.6(2) . . . . ?
C5 C10 C9 C8 -0.7(4) . . . . ?
C9 C8 C7 C6 0.6(4) . . . . ?
Cl1 C8 C7 C6 179.7(2) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C1 C2 C3 C4 24.9(3) . . . . ?
C1 O1 C4 C3 -16.8(3) . . . . ?
C2 C3 C4 O1 -6.4(4) . . . . ?
O1 C1 N1 S1 -58.6(3) . . . . ?
C2 C1 N1 S1 -175.6(2) . . . . ?
O3 S1 N1 C1 -42.0(2) . . . . ?
O2 S1 N1 C1 -170.3(2) . . . . ?
C5 S1 N1 C1 74.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.090
_exptl_crystal_recrystallization_method 'Pentane/dichloromethane diffusion'
_database_code_depnum_ccdc_archive 'CCDC 1015067'
#######################################################################
#
#                 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_14086

#=========================================================================
# Data for compound 8 (local labelling 14086)
#========================================================================= 

# start Validation Reply Form
_vrf_RINTA01_14086               
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE:The quality of the data was poor due to the low crystal quality.
The crystals grown as very thin plates (ca. 0.3 x 0.3 x 0.01mm) that were
very weakly diffracting, thus a large proportion of almost 
"unobserved" reflections are being used in the refinement.  Attempts to 
grow single crystals of higher quality were unsuccessful. However, the 
structure solution and refinement are unambiguous and fully consistent 
with the spectroscopic characterization of the compound. The final model
 is of a reasonable quality.
;

_vrf_PLAT020_14086               
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.279       
RESPONSE: Same as RINTA01
;

_vrf_PLAT340_14086               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0115 Ang.      
RESPONSE: This is also presumably due to the low quality data. See RINTA01.
;

_vrf_RFACR01_14086               
;
PROBLEM: The value of the weighted R factor is > 0.25      
RESPONSE: Same as RINTA01. 
;
_vrf_PLAT084_14086               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.29 Why ?       
RESPONSE: Same as RINTA01. 
;
_vrf_PLAT906_14086               
;
PROBLEM: Large K value in the Analysis of Variance        
RESPONSE: Same as RINTA01. 
;




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 Cl6 N2 O6 S2'
_chemical_formula_sum            'C5 H8 Cl6 N2 O6 S2'
_chemical_formula_weight         468.95

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'
Cl Cl 0.3639 0.7018 '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   'P 21/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                   14.4775(15)
_cell_length_b                   10.2636(7)
_cell_length_c                   11.6608(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.253(8)
_cell_angle_gamma                90.00
_cell_volume                     1625.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    6172
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      67.6

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    12.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'


_exptl_special_details           
; 
 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' 
;

_diffrn_ambient_temperature      93(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  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            43520
_diffrn_reflns_av_R_equivalents  0.2791
_diffrn_reflns_av_sigmaI/netI    0.4394
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         66.59
_reflns_number_total             2861
_reflns_number_gt                1883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r12'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1312P)²+3.3223P] 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         2861
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.0974
_refine_ls_wR_factor_ref         0.2853
_refine_ls_wR_factor_gt          0.2463
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0370(6) 0.7905(8) 0.5592(7) 0.0473(19) Uani 1 1 d . . .
H1A H -0.1075 0.8073 0.5133 0.057 Uiso 1 1 calc R . .
H1B H -0.0105 0.8674 0.6115 0.057 Uiso 1 1 calc R . .
C2 C 0.2327(7) 0.7150(10) 0.6748(8) 0.058(2) Uani 1 1 d . . .
H2A H 0.2048 0.6304 0.6877 0.070 Uiso 1 1 calc R . .
H2B H 0.2076 0.7837 0.7160 0.070 Uiso 1 1 calc R . .
C3 C 0.3446(7) 0.7102(10) 0.7287(9) 0.063(2) Uani 1 1 d . . .
C4 C -0.2203(7) 0.6084(9) 0.6925(8) 0.056(2) Uani 1 1 d . . .
H4A H -0.1572 0.6258 0.7593 0.068 Uiso 1 1 calc R . .
H4B H -0.2488 0.5276 0.7125 0.068 Uiso 1 1 calc R . .
C5 C -0.2899(7) 0.7203(9) 0.6817(9) 0.060(2) Uani 1 1 d . . .
Cl1 Cl 0.38948(18) 0.5845(3) 0.6596(3) 0.0762(8) Uani 1 1 d . . .
Cl2 Cl 0.39524(18) 0.8619(2) 0.7050(3) 0.0722(8) Uani 1 1 d . . .
Cl3 Cl 0.37486(19) 0.6808(3) 0.8868(2) 0.0810(9) Uani 1 1 d . . .
Cl4 Cl -0.2341(2) 0.8682(2) 0.6576(3) 0.0728(8) Uani 1 1 d . . .
Cl5 Cl -0.31451(17) 0.7287(2) 0.8199(2) 0.0644(7) Uani 1 1 d . . .
Cl6 Cl -0.40115(17) 0.6953(3) 0.5580(2) 0.0783(9) Uani 1 1 d . . .
N1 N 0.0146(5) 0.7779(7) 0.4717(6) 0.0501(17) Uani 1 1 d D . .
N2 N -0.0293(5) 0.6767(6) 0.6385(6) 0.0470(16) Uani 1 1 d D . .
O1 O 0.1261(4) 0.8614(6) 0.3725(5) 0.0557(15) Uani 1 1 d . . .
O2 O 0.1290(4) 0.9522(5) 0.5678(5) 0.0557(15) Uani 1 1 d . . .
O3 O 0.2035(4) 0.7421(6) 0.5475(5) 0.0562(15) Uani 1 1 d . . .
O4 O -0.1092(4) 0.5356(5) 0.4589(5) 0.0499(14) Uani 1 1 d . . .
O5 O -0.0615(4) 0.4489(5) 0.6692(5) 0.0518(14) Uani 1 1 d . . .
O6 O -0.2031(4) 0.5921(6) 0.5791(5) 0.0503(14) Uani 1 1 d . . .
S1 S 0.11867(15) 0.8438(2) 0.48932(18) 0.0485(6) Uani 1 1 d . . .
S2 S -0.09718(15) 0.55233(19) 0.58366(19) 0.0481(6) Uani 1 1 d . . .
H1 H 0.013(7) 0.712(7) 0.419(7) 0.07(3) Uiso 1 1 d D . .
H2 H 0.026(6) 0.667(13) 0.704(8) 0.11(4) Uiso 1 1 d 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 0.057(5) 0.042(5) 0.040(4) 0.000(3) 0.014(4) -0.001(4)
C2 0.062(5) 0.061(6) 0.046(5) 0.000(4) 0.012(4) -0.010(4)
C3 0.057(5) 0.062(6) 0.059(6) 0.002(4) 0.007(4) 0.001(4)
C4 0.056(5) 0.057(5) 0.052(5) 0.002(4) 0.013(4) 0.002(4)
C5 0.058(5) 0.061(6) 0.057(5) 0.003(4) 0.015(4) 0.008(4)
Cl1 0.0644(15) 0.0654(16) 0.0910(19) 0.0020(13) 0.0169(13) 0.0095(11)
Cl2 0.0639(15) 0.0626(16) 0.0840(18) -0.0057(12) 0.0178(12) -0.0157(11)
Cl3 0.0644(15) 0.103(2) 0.0590(15) 0.0043(13) -0.0002(11) -0.0114(13)
Cl4 0.0971(19) 0.0495(14) 0.0820(17) 0.0009(11) 0.0441(14) 0.0026(12)
Cl5 0.0653(14) 0.0747(16) 0.0521(13) -0.0010(10) 0.0190(10) 0.0068(11)
Cl6 0.0505(13) 0.120(2) 0.0563(14) 0.0013(13) 0.0080(10) 0.0117(13)
N1 0.057(4) 0.040(4) 0.050(4) -0.007(3) 0.014(3) -0.005(3)
N2 0.050(4) 0.040(4) 0.047(4) -0.003(3) 0.011(3) -0.004(3)
O1 0.056(3) 0.065(4) 0.042(3) 0.003(3) 0.012(3) -0.007(3)
O2 0.064(4) 0.044(3) 0.052(3) -0.008(3) 0.012(3) -0.006(3)
O3 0.055(3) 0.055(3) 0.044(3) 0.004(2) -0.001(2) 0.005(3)
O4 0.054(3) 0.052(3) 0.040(3) -0.010(2) 0.012(2) -0.002(3)
O5 0.063(3) 0.042(3) 0.046(3) 0.008(2) 0.014(3) 0.004(3)
O6 0.053(3) 0.051(3) 0.042(3) -0.002(2) 0.012(2) -0.002(3)
S1 0.0504(12) 0.0412(11) 0.0466(11) 0.0009(8) 0.0073(9) -0.0009(8)
S2 0.0487(11) 0.0409(11) 0.0502(12) 0.0001(8) 0.0114(9) 0.0012(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.465(11) . ?
C1 N2 1.469(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O3 1.423(11) . ?
C2 C3 1.523(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 Cl1 1.760(11) . ?
C3 Cl3 1.767(10) . ?
C3 Cl2 1.783(10) . ?
C4 O6 1.437(11) . ?
C4 C5 1.504(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 Cl5 1.769(10) . ?
C5 Cl6 1.770(10) . ?
C5 Cl4 1.787(11) . ?
N1 S1 1.598(7) . ?
N1 H1 0.91(2) . ?
N2 S2 1.603(7) . ?
N2 H2 0.91(2) . ?
O1 S1 1.415(6) . ?
O2 S1 1.416(6) . ?
O3 S1 1.575(6) . ?
O4 S2 1.415(6) . ?
O5 S2 1.425(5) . ?
O6 S2 1.571(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 115.0(7) . . ?
N1 C1 H1A 108.5 . . ?
N2 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
N2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
O3 C2 C3 109.0(7) . . ?
O3 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
O3 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C2 C3 Cl1 110.1(7) . . ?
C2 C3 Cl3 106.2(7) . . ?
Cl1 C3 Cl3 110.8(5) . . ?
C2 C3 Cl2 110.1(7) . . ?
Cl1 C3 Cl2 109.4(6) . . ?
Cl3 C3 Cl2 110.1(5) . . ?
O6 C4 C5 109.6(7) . . ?
O6 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
O6 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 Cl5 107.5(6) . . ?
C4 C5 Cl6 110.6(7) . . ?
Cl5 C5 Cl6 109.6(5) . . ?
C4 C5 Cl4 109.6(7) . . ?
Cl5 C5 Cl4 110.3(5) . . ?
Cl6 C5 Cl4 109.2(5) . . ?
C1 N1 S1 123.9(5) . . ?
C1 N1 H1 130(7) . . ?
S1 N1 H1 102(6) . . ?
C1 N2 S2 118.7(5) . . ?
C1 N2 H2 118(9) . . ?
S2 N2 H2 119(9) . . ?
C2 O3 S1 119.0(6) . . ?
C4 O6 S2 118.5(5) . . ?
O1 S1 O2 119.7(4) . . ?
O1 S1 O3 101.1(4) . . ?
O2 S1 O3 110.5(3) . . ?
O1 S1 N1 108.2(4) . . ?
O2 S1 N1 107.5(4) . . ?
O3 S1 N1 109.6(4) . . ?
O4 S2 O5 121.0(4) . . ?
O4 S2 O6 103.0(3) . . ?
O5 S2 O6 109.3(3) . . ?
O4 S2 N2 110.3(4) . . ?
O5 S2 N2 106.9(3) . . ?
O6 S2 N2 105.2(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
O3 C2 C3 Cl1 -61.6(9) . . . . ?
O3 C2 C3 Cl3 178.4(6) . . . . ?
O3 C2 C3 Cl2 59.2(9) . . . . ?
O6 C4 C5 Cl5 176.2(6) . . . . ?
O6 C4 C5 Cl6 56.5(9) . . . . ?
O6 C4 C5 Cl4 -63.9(8) . . . . ?
N2 C1 N1 S1 -102.0(8) . . . . ?
N1 C1 N2 S2 -78.3(8) . . . . ?
C3 C2 O3 S1 -136.6(7) . . . . ?
C5 C4 O6 S2 142.8(6) . . . . ?
C2 O3 S1 O1 168.9(6) . . . . ?
C2 O3 S1 O2 41.2(7) . . . . ?
C2 O3 S1 N1 -77.1(7) . . . . ?
C1 N1 S1 O1 -154.7(6) . . . . ?
C1 N1 S1 O2 -24.2(7) . . . . ?
C1 N1 S1 O3 95.9(7) . . . . ?
C4 O6 S2 O4 175.6(6) . . . . ?
C4 O6 S2 O5 45.8(6) . . . . ?
C4 O6 S2 N2 -68.7(6) . . . . ?
C1 N2 S2 O4 35.2(7) . . . . ?
C1 N2 S2 O5 168.5(6) . . . . ?
C1 N2 S2 O6 -75.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.183
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.155
_exptl_crystal_recrystallization_method 'Pentane/dichloromethane diffusion'
_database_code_depnum_ccdc_archive 'CCDC 1015068'
#######################################################################
#
#                 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_jcm374

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 Cl3 N O6 S'
_chemical_formula_sum            'C15 H22 Cl3 N O6 S'
_chemical_formula_weight         450.75

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'
Cl Cl 0.3639 0.7018 '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   'P 21/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                   10.2017(2)
_cell_length_b                   13.6673(4)
_cell_length_c                   16.8782(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.800(5)
_cell_angle_gamma                90.00
_cell_volume                     2062.23(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    8958
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      66.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    5.247
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'


_exptl_special_details           
; 
 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' 
;

_diffrn_ambient_temperature      93(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  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            34944
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.40
_diffrn_reflns_theta_max         66.68
_reflns_number_total             3583
_reflns_number_gt                3456
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r12'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0650P)²+2.8299P] 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         3583
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6150(3) 0.75251(17) 0.46391(16) 0.0197(5) Uani 1 1 d . . .
H1A H 0.5910 0.7389 0.4001 0.024 Uiso 1 1 calc R . .
C2 C 0.7804(3) 0.72837(19) 0.52416(17) 0.0250(5) Uani 1 1 d . . .
H2A H 0.8102 0.7484 0.5869 0.030 Uiso 1 1 calc R . .
H2B H 0.7940 0.6567 0.5241 0.030 Uiso 1 1 calc R . .
C3 C 0.8832(3) 0.7781(2) 0.4946(2) 0.0335(6) Uani 1 1 d . . .
H3A H 0.8509 0.7607 0.4309 0.040 Uiso 1 1 calc R . .
H3B H 0.8740 0.8500 0.4977 0.040 Uiso 1 1 calc R . .
C4 C 1.0463(3) 0.7491(3) 0.5527(3) 0.0531(9) Uani 1 1 d . . .
H4A H 1.0811 0.7704 0.6152 0.080 Uiso 1 1 calc R . .
H4B H 1.1071 0.7804 0.5293 0.080 Uiso 1 1 calc R . .
H4C H 1.0558 0.6779 0.5512 0.080 Uiso 1 1 calc R . .
C5 C 0.2477(3) 0.8892(2) 0.39229(17) 0.0282(6) Uani 1 1 d . . .
H5A H 0.3094 0.9291 0.4467 0.034 Uiso 1 1 calc R . .
H5B H 0.2331 0.8239 0.4122 0.034 Uiso 1 1 calc R . .
C6 C 0.0970(3) 0.9382(2) 0.33563(18) 0.0291(6) Uani 1 1 d . . .
C7 C 0.5095(3) 0.69148(17) 0.48279(16) 0.0205(5) Uani 1 1 d . . .
C8 C 0.5073(3) 0.69640(18) 0.56466(16) 0.0211(5) Uani 1 1 d . . .
C9 C 0.4126(3) 0.63848(18) 0.58364(17) 0.0237(5) Uani 1 1 d . . .
H9 H 0.4152 0.6420 0.6406 0.028 Uiso 1 1 calc R . .
C10 C 0.3152(3) 0.57593(19) 0.51673(18) 0.0250(5) Uani 1 1 d . . .
C11 C 0.3115(3) 0.56878(19) 0.43339(17) 0.0247(5) Uani 1 1 d . . .
H11 H 0.2427 0.5261 0.3879 0.030 Uiso 1 1 calc R . .
C12 C 0.4104(3) 0.62523(18) 0.41780(16) 0.0220(5) Uani 1 1 d . . .
C13 C 0.6045(4) 0.7761(2) 0.70885(18) 0.0371(7) Uani 1 1 d . . .
H13A H 0.5032 0.7923 0.6972 0.056 Uiso 1 1 calc R . .
H13B H 0.6729 0.8293 0.7430 0.056 Uiso 1 1 calc R . .
H13C H 0.6374 0.7154 0.7439 0.056 Uiso 1 1 calc R . .
C14 C 0.2343(3) 0.5019(2) 0.61488(19) 0.0334(6) Uani 1 1 d . . .
H14A H 0.3348 0.4757 0.6536 0.050 Uiso 1 1 calc R . .
H14B H 0.1595 0.4553 0.6124 0.050 Uiso 1 1 calc R . .
H14C H 0.2230 0.5642 0.6397 0.050 Uiso 1 1 calc R . .
C15 C 0.3112(3) 0.5616(2) 0.26804(18) 0.0319(6) Uani 1 1 d . . .
H15A H 0.3236 0.4933 0.2880 0.048 Uiso 1 1 calc R . .
H15B H 0.3259 0.5670 0.2149 0.048 Uiso 1 1 calc R . .
H15C H 0.2103 0.5839 0.2523 0.048 Uiso 1 1 calc R . .
Cl1 Cl 0.11833(7) 1.05620(5) 0.29967(5) 0.0363(2) Uani 1 1 d . . .
Cl2 Cl -0.01737(8) 0.86766(6) 0.23905(5) 0.0490(2) Uani 1 1 d . . .
Cl3 Cl 0.00990(8) 0.94972(6) 0.40360(5) 0.0414(2) Uani 1 1 d . . .
N1 N 0.5918(2) 0.85927(14) 0.47032(13) 0.0183(4) Uani 1 1 d D . .
O1 O 0.5280(2) 0.89901(14) 0.31287(12) 0.0279(4) Uani 1 1 d . . .
O2 O 0.48937(19) 1.02007(13) 0.40801(11) 0.0241(4) Uani 1 1 d . . .
O3 O 0.32284(19) 0.87915(13) 0.33929(11) 0.0267(4) Uani 1 1 d . . .
O4 O 0.41912(19) 0.62119(13) 0.33944(12) 0.0265(4) Uani 1 1 d . . .
O5 O 0.6046(2) 0.76354(13) 0.62492(11) 0.0254(4) Uani 1 1 d . . .
O6 O 0.2136(2) 0.51731(14) 0.52572(13) 0.0319(4) Uani 1 1 d . . .
S1 S 0.48979(6) 0.92077(4) 0.38133(4) 0.01956(17) Uani 1 1 d . . .
H1 H 0.595(3) 0.883(2) 0.5200(15) 0.033(8) Uiso 1 1 d 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 0.0225(12) 0.0162(12) 0.0214(11) 0.0006(9) 0.0114(10) 0.0009(9)
C2 0.0243(12) 0.0222(13) 0.0295(13) 0.0039(10) 0.0138(11) 0.0053(10)
C3 0.0243(13) 0.0341(16) 0.0455(16) 0.0085(12) 0.0195(12) 0.0055(11)
C4 0.0277(16) 0.060(2) 0.072(2) 0.0237(19) 0.0248(16) 0.0110(14)
C5 0.0225(13) 0.0365(15) 0.0255(13) 0.0019(11) 0.0115(11) -0.0009(11)
C6 0.0235(13) 0.0355(15) 0.0267(13) -0.0013(11) 0.0110(11) -0.0036(11)
C7 0.0214(11) 0.0183(12) 0.0225(12) 0.0022(9) 0.0112(10) 0.0015(9)
C8 0.0242(12) 0.0172(12) 0.0212(12) 0.0002(9) 0.0105(10) 0.0006(9)
C9 0.0290(13) 0.0216(13) 0.0238(12) 0.0012(9) 0.0153(11) 0.0001(10)
C10 0.0257(13) 0.0209(13) 0.0321(13) 0.0019(10) 0.0169(11) -0.0005(10)
C11 0.0223(12) 0.0241(13) 0.0265(13) -0.0028(10) 0.0107(10) -0.0023(10)
C12 0.0228(12) 0.0223(13) 0.0215(12) -0.0001(9) 0.0112(10) 0.0032(9)
C13 0.0590(19) 0.0341(16) 0.0244(13) -0.0077(11) 0.0252(13) -0.0178(14)
C14 0.0383(15) 0.0326(15) 0.0362(15) 0.0055(12) 0.0235(13) -0.0035(12)
C15 0.0295(14) 0.0423(17) 0.0233(13) -0.0110(11) 0.0122(11) -0.0082(12)
Cl1 0.0313(4) 0.0363(4) 0.0437(4) 0.0090(3) 0.0201(3) 0.0047(3)
Cl2 0.0293(4) 0.0516(5) 0.0445(4) -0.0171(3) 0.0005(3) -0.0017(3)
Cl3 0.0308(4) 0.0589(5) 0.0420(4) 0.0094(3) 0.0236(3) 0.0042(3)
N1 0.0223(10) 0.0171(10) 0.0155(9) 0.0016(8) 0.0090(8) 0.0032(8)
O1 0.0377(10) 0.0302(10) 0.0216(9) 0.0036(7) 0.0189(8) 0.0064(8)
O2 0.0296(9) 0.0188(9) 0.0249(9) 0.0020(7) 0.0140(7) 0.0039(7)
O3 0.0221(9) 0.0323(10) 0.0223(9) -0.0044(7) 0.0080(7) 0.0006(7)
O4 0.0270(9) 0.0322(10) 0.0219(9) -0.0077(7) 0.0131(7) -0.0064(7)
O5 0.0353(10) 0.0232(9) 0.0206(8) -0.0041(7) 0.0158(8) -0.0088(7)
O6 0.0342(10) 0.0318(11) 0.0360(10) -0.0025(8) 0.0220(9) -0.0107(8)
S1 0.0219(3) 0.0206(3) 0.0173(3) 0.0022(2) 0.0104(2) 0.0037(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.490(3) . ?
C1 C7 1.512(3) . ?
C1 C2 1.529(3) . ?
C1 H1A 1.0000 . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 O3 1.438(3) . ?
C5 C6 1.520(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 Cl3 1.764(3) . ?
C6 Cl2 1.765(3) . ?
C6 Cl1 1.773(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.406(3) . ?
C8 O5 1.375(3) . ?
C8 C9 1.400(3) . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 O6 1.375(3) . ?
C10 C11 1.392(4) . ?
C11 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C12 O4 1.368(3) . ?
C13 O5 1.428(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O6 1.430(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O4 1.431(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 S1 1.5936(19) . ?
N1 H1 0.883(18) . ?
O1 S1 1.4175(18) . ?
O2 S1 1.4305(18) . ?
O3 S1 1.6010(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C7 111.77(19) . . ?
N1 C1 C2 109.02(19) . . ?
C7 C1 C2 114.2(2) . . ?
N1 C1 H1A 107.2 . . ?
C7 C1 H1A 107.2 . . ?
C2 C1 H1A 107.2 . . ?
C3 C2 C1 113.6(2) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 112.6(2) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 C6 109.4(2) . . ?
O3 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
O3 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C5 C6 Cl3 107.68(18) . . ?
C5 C6 Cl2 111.0(2) . . ?
Cl3 C6 Cl2 109.47(14) . . ?
C5 C6 Cl1 111.26(18) . . ?
Cl3 C6 Cl1 108.97(15) . . ?
Cl2 C6 Cl1 108.44(15) . . ?
C8 C7 C12 117.1(2) . . ?
C8 C7 C1 122.4(2) . . ?
C12 C7 C1 120.5(2) . . ?
O5 C8 C7 114.5(2) . . ?
O5 C8 C9 122.7(2) . . ?
C7 C8 C9 122.8(2) . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
O6 C10 C9 123.6(2) . . ?
O6 C10 C11 114.6(2) . . ?
C9 C10 C11 121.8(2) . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
O4 C12 C11 123.4(2) . . ?
O4 C12 C7 115.0(2) . . ?
C11 C12 C7 121.5(2) . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 S1 120.16(16) . . ?
C1 N1 H1 119(2) . . ?
S1 N1 H1 114(2) . . ?
C5 O3 S1 117.56(15) . . ?
C12 O4 C15 117.1(2) . . ?
C8 O5 C13 117.96(19) . . ?
C10 O6 C14 117.7(2) . . ?
O1 S1 O2 119.96(11) . . ?
O1 S1 N1 110.26(11) . . ?
O2 S1 N1 107.66(10) . . ?
O1 S1 O3 102.45(10) . . ?
O2 S1 O3 108.22(10) . . ?
N1 S1 O3 107.62(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
N1 C1 C2 C3 -63.6(3) . . . . ?
C7 C1 C2 C3 170.6(2) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
O3 C5 C6 Cl3 -179.56(17) . . . . ?
O3 C5 C6 Cl2 60.6(3) . . . . ?
O3 C5 C6 Cl1 -60.2(3) . . . . ?
N1 C1 C7 C8 -59.6(3) . . . . ?
C2 C1 C7 C8 64.7(3) . . . . ?
N1 C1 C7 C12 121.6(2) . . . . ?
C2 C1 C7 C12 -114.0(3) . . . . ?
C12 C7 C8 O5 -179.0(2) . . . . ?
C1 C7 C8 O5 2.2(3) . . . . ?
C12 C7 C8 C9 0.4(4) . . . . ?
C1 C7 C8 C9 -178.4(2) . . . . ?
O5 C8 C9 C10 177.7(2) . . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C8 C9 C10 O6 -178.0(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
O6 C10 C11 C12 -179.9(2) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 O4 177.8(2) . . . . ?
C10 C11 C12 C7 -2.4(4) . . . . ?
C8 C7 C12 O4 -178.5(2) . . . . ?
C1 C7 C12 O4 0.3(3) . . . . ?
C8 C7 C12 C11 1.7(3) . . . . ?
C1 C7 C12 C11 -179.5(2) . . . . ?
C7 C1 N1 S1 -96.8(2) . . . . ?
C2 C1 N1 S1 135.95(18) . . . . ?
C6 C5 O3 S1 127.25(19) . . . . ?
C11 C12 O4 C15 5.5(3) . . . . ?
C7 C12 O4 C15 -174.4(2) . . . . ?
C7 C8 O5 C13 177.3(2) . . . . ?
C9 C8 O5 C13 -2.1(4) . . . . ?
C9 C10 O6 C14 -16.1(4) . . . . ?
C11 C10 O6 C14 164.9(2) . . . . ?
C1 N1 S1 O1 -46.9(2) . . . . ?
C1 N1 S1 O2 -179.46(17) . . . . ?
C1 N1 S1 O3 64.09(19) . . . . ?
C5 O3 S1 O1 179.96(18) . . . . ?
C5 O3 S1 O2 -52.4(2) . . . . ?
C5 O3 S1 N1 63.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        66.68
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.073
_exptl_crystal_recrystallization_method 'Pentane/dichloromethane diffusion'
_database_code_depnum_ccdc_archive 'CCDC 1015069'
