# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Jason Perman'
_publ_contact_author_email       jasonperman@gmail.com
loop_
_publ_author_name
X.-X.P.Zhang
J.A.Perman
J.V.Ruppel
V.Subbarayan
'Shifa Zhu'

data_sv_iv_240_0m
_database_code_depnum_ccdc_archive 'CCDC 724786'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Cl4 N O3 S'
_chemical_formula_weight         365.04

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   P2(1)

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

_cell_length_a                   10.4908(6)
_cell_length_b                   6.0700(4)
_cell_length_c                   12.0008(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.370(3)
_cell_angle_gamma                90.00
_cell_volume                     740.29(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3256
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      66.69

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    8.624
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.1299
_exptl_absorpt_correction_T_max  0.4793
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6397
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         68.13
_reflns_number_total             2367
_reflns_number_gt                2228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_chemical_absolute_configuration ad
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+0.1959P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_number_reflns         2367
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_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 0.42192(7) 0.56239(14) 0.29962(6) 0.04346(19) Uani 1 1 d . . .
Cl1 Cl 1.09715(8) -0.1027(2) 0.29579(9) 0.0745(3) Uani 1 1 d . . .
Cl4 Cl 0.13672(10) 0.3693(2) 0.01526(11) 0.0892(4) Uani 1 1 d . . .
C1 C 0.9792(3) 0.0779(7) 0.3224(3) 0.0513(8) Uani 1 1 d . . .
C4 C 0.7848(3) 0.3575(6) 0.3566(3) 0.0451(7) Uani 1 1 d . . .
C6 C 0.9001(3) 0.0121(7) 0.3934(3) 0.0567(9) Uani 1 1 d . . .
H6 H 0.9122 -0.1243 0.4298 0.068 Uiso 1 1 calc R . .
C7 C 0.6820(3) 0.5162(6) 0.3710(3) 0.0470(8) Uani 1 1 d . . .
H7 H 0.6802 0.6560 0.3297 0.056 Uiso 1 1 calc R . .
C8 C 0.6304(3) 0.5256(7) 0.4741(3) 0.0564(9) Uani 1 1 d . . .
H8A H 0.6014 0.6675 0.4957 0.068 Uiso 1 1 calc R . .
H8B H 0.6708 0.4307 0.5382 0.068 Uiso 1 1 calc R . .
C9 C 0.3667(4) 0.2404(6) 0.1559(3) 0.0538(8) Uani 1 1 d . . .
H9A H 0.3181 0.1923 0.2105 0.065 Uiso 1 1 calc R . .
H9B H 0.4448 0.1497 0.1658 0.065 Uiso 1 1 calc R . .
C5 C 0.8022(4) 0.1555(7) 0.4088(3) 0.0558(9) Uani 1 1 d . . .
H5 H 0.7476 0.1130 0.4554 0.067 Uiso 1 1 calc R . .
C10 C 0.2823(3) 0.2188(6) 0.0347(3) 0.0525(8) Uani 1 1 d . . .
C2 C 0.9659(4) 0.2817(8) 0.2720(3) 0.0653(11) Uani 1 1 d . . .
H2 H 1.0215 0.3256 0.2266 0.078 Uiso 1 1 calc R . .
C3 C 0.8688(3) 0.4211(7) 0.2896(3) 0.0579(9) Uani 1 1 d . . .
H3 H 0.8595 0.5601 0.2560 0.069 Uiso 1 1 calc R . .
Cl3 Cl 0.24525(15) -0.0643(2) 0.01394(10) 0.0882(4) Uani 1 1 d . . .
Cl2 Cl 0.36710(15) 0.3087(3) -0.06643(10) 0.0972(5) Uani 1 1 d . . .
N1 N 0.5511(2) 0.4204(5) 0.3685(2) 0.0417(6) Uani 1 1 d . . .
O3 O 0.4030(2) 0.4691(4) 0.17501(18) 0.0475(5) Uani 1 1 d . . .
O1 O 0.4471(3) 0.7888(4) 0.2899(2) 0.0628(7) Uani 1 1 d . . .
O2 O 0.3157(2) 0.4951(5) 0.3459(2) 0.0624(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0452(4) 0.0434(4) 0.0399(4) -0.0011(3) 0.0070(3) 0.0112(3)
Cl1 0.0454(4) 0.0989(8) 0.0773(6) -0.0094(6) 0.0117(4) 0.0241(5)
Cl4 0.0511(5) 0.1048(10) 0.1001(8) 0.0207(7) -0.0030(5) 0.0080(6)
C1 0.0339(14) 0.072(2) 0.0460(16) -0.0040(19) 0.0067(12) 0.0095(17)
C4 0.0403(15) 0.053(2) 0.0410(15) -0.0013(14) 0.0090(12) -0.0007(14)
C6 0.0571(19) 0.053(2) 0.060(2) 0.0048(17) 0.0148(17) 0.0090(16)
C7 0.0466(16) 0.048(2) 0.0465(16) -0.0030(14) 0.0111(13) -0.0060(14)
C8 0.0494(17) 0.077(3) 0.0403(16) -0.0088(17) 0.0059(13) 0.0113(17)
C9 0.066(2) 0.0389(18) 0.0486(17) -0.0020(14) -0.0004(15) 0.0028(16)
C5 0.0538(19) 0.060(2) 0.060(2) 0.0011(18) 0.0271(16) -0.0018(17)
C10 0.0559(19) 0.054(2) 0.0457(17) -0.0002(15) 0.0081(14) -0.0074(16)
C2 0.058(2) 0.092(3) 0.0536(19) 0.014(2) 0.0281(17) 0.015(2)
C3 0.0566(19) 0.068(3) 0.0530(19) 0.0126(18) 0.0209(15) 0.0079(18)
Cl3 0.1215(9) 0.0637(7) 0.0673(6) -0.0100(5) 0.0004(6) -0.0270(6)
Cl2 0.1224(10) 0.1176(11) 0.0666(6) -0.0277(7) 0.0518(6) -0.0517(8)
N1 0.0380(12) 0.0459(16) 0.0402(13) 0.0001(11) 0.0074(10) 0.0012(12)
O3 0.0542(12) 0.0477(13) 0.0371(11) 0.0014(9) 0.0048(9) 0.0016(10)
O1 0.0807(18) 0.0423(15) 0.0586(14) -0.0024(11) 0.0047(12) 0.0119(13)
O2 0.0497(12) 0.080(2) 0.0609(15) 0.0021(13) 0.0200(11) 0.0148(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
S1 O1 1.410(3) . ?
S1 O2 1.423(3) . ?
S1 O3 1.565(2) . ?
S1 N1 1.645(3) . ?
Cl1 C1 1.741(4) . ?
Cl4 C10 1.745(4) . ?
C1 C2 1.369(6) . ?
C1 C6 1.388(5) . ?
C4 C5 1.368(5) . ?
C4 C3 1.387(5) . ?
C4 C7 1.487(5) . ?
C6 C5 1.394(5) . ?
C7 C8 1.470(5) . ?
C7 N1 1.486(4) . ?
C8 N1 1.477(4) . ?
C9 O3 1.443(4) . ?
C9 C10 1.509(5) . ?
C10 Cl2 1.760(4) . ?
C10 Cl3 1.766(4) . ?
C2 C3 1.381(5) . ?

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
O1 S1 O2 119.54(17) . . ?
O1 S1 O3 104.82(14) . . ?
O2 S1 O3 110.07(15) . . ?
O1 S1 N1 113.85(16) . . ?
O2 S1 N1 106.29(14) . . ?
O3 S1 N1 100.62(12) . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 Cl1 119.2(3) . . ?
C6 C1 Cl1 119.5(3) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 C7 123.1(3) . . ?
C3 C4 C7 118.0(3) . . ?
C1 C6 C5 118.3(4) . . ?
C8 C7 N1 60.0(2) . . ?
C8 C7 C4 123.5(3) . . ?
N1 C7 C4 115.9(3) . . ?
C7 C8 N1 60.5(2) . . ?
O3 C9 C10 107.8(3) . . ?
C4 C5 C6 121.2(3) . . ?
C9 C10 Cl4 111.6(3) . . ?
C9 C10 Cl2 111.2(3) . . ?
Cl4 C10 Cl2 108.7(2) . . ?
C9 C10 Cl3 106.0(3) . . ?
Cl4 C10 Cl3 109.6(2) . . ?
Cl2 C10 Cl3 109.6(2) . . ?
C1 C2 C3 119.0(3) . . ?
C2 C3 C4 121.2(4) . . ?
C8 N1 C7 59.5(2) . . ?
C8 N1 S1 115.0(2) . . ?
C7 N1 S1 116.5(2) . . ?
C9 O3 S1 117.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        68.13
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.050