Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
E.R.T.Tiekink
'Fong Shenn Kuan.'
F.Mohr
P.P.Tadbuppa

_publ_contact_author_name        'Edward R.T. Tiekink'
_publ_contact_author_address     
;
Department of Chemistry
The University of Texas at San Antonio
One UTSA Circle
San Antonio
Texas
78249-0698
UNITED STATES OF AMERICA
;

_publ_contact_author_email       EDWARD.TIEKINK@UTSA.EDU

_publ_requested_journal          'Cryst Eng. Comm.'

_publ_section_title              
;
Principles of crystal packing in
O-isopropyl-N-aryl-thiocarbamides: iPrOC(=S)N(H)C6H4-4-Y: Y = H, Cl, and
Me
;

data_(3)
_database_code_depnum_ccdc_archive 'CCDC 635332'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N O S'
_chemical_formula_sum            'C11 H15 N O S'
_chemical_formula_weight         209.30

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           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.1410(5)
_cell_length_b                   14.8045(10)
_cell_length_c                   9.7157(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.931(1)
_cell_angle_gamma                90
_cell_volume                     1145.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2116
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      26.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   '(SADABS, Bruker, 2000 & Blessing, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART CCD'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11187
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.6
_diffrn_reflns_theta_max         30.0
_reflns_number_total             3339
_reflns_number_gt                2461
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_structure_solution    'SIR92 (Altomare et al., 1992)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHEXLTL (Bruker, 2000)'

_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^)+(0.0792P)^2^+0.4348P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3339
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_gt           0.064
_refine_ls_wR_factor_ref         0.166
_refine_ls_wR_factor_gt          0.153
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20914(8) 0.41829(4) 0.56769(5) 0.0532(2) Uani 1 1 d . . .
O1 O 0.25963(18) 0.35161(11) 0.32700(15) 0.0515(4) Uani 1 1 d . . .
N1 N 0.0122(2) 0.41612(11) 0.31607(17) 0.0359(4) Uani 1 1 d . . .
H1 H -0.0569 0.4431 0.3599 0.043 Uiso 1 1 calc R . .
C1 C 0.1603(2) 0.39353(13) 0.39661(19) 0.0345(4) Uani 1 1 d . . .
C2 C -0.0496(2) 0.40271(12) 0.16934(19) 0.0315(4) Uani 1 1 d . . .
C3 C -0.1603(2) 0.46706(13) 0.0995(2) 0.0374(4) Uani 1 1 d . . .
H3 H -0.1907 0.5165 0.1495 0.045 Uiso 1 1 calc R . .
C4 C -0.2263(3) 0.45894(14) -0.0429(2) 0.0407(5) Uani 1 1 d . . .
H4 H -0.3016 0.5029 -0.0885 0.049 Uiso 1 1 calc R . .
C5 C -0.1832(2) 0.38680(14) -0.1198(2) 0.0376(4) Uani 1 1 d . . .
C5' C -0.2508(3) 0.37918(17) -0.2763(2) 0.0516(6) Uani 1 1 d . . .
H5'1 H -0.3498 0.4168 -0.3027 0.077 Uiso 1 1 calc R . .
H5'2 H -0.2801 0.3168 -0.3002 0.077 Uiso 1 1 calc R . .
H5'3 H -0.1658 0.3990 -0.3264 0.077 Uiso 1 1 calc R . .
C6 C -0.0762(2) 0.32218(13) -0.0478(2) 0.0387(4) Uani 1 1 d . . .
H6 H -0.0474 0.2721 -0.0975 0.046 Uiso 1 1 calc R . .
C7 C -0.0098(2) 0.32877(13) 0.0955(2) 0.0367(4) Uani 1 1 d . . .
H7 H 0.0615 0.2834 0.1419 0.044 Uiso 1 1 calc R . .
C8 C 0.4250(3) 0.31724(19) 0.3993(2) 0.0577(7) Uani 1 1 d . . .
H8 H 0.4547 0.3431 0.4952 0.069 Uiso 1 1 calc R . .
C9 C 0.4104(4) 0.2173(2) 0.4082(4) 0.0778(9) Uani 1 1 d . . .
H9A H 0.3305 0.2022 0.4661 0.117 Uiso 1 1 calc R . .
H9B H 0.5191 0.1918 0.4497 0.117 Uiso 1 1 calc R . .
H9C H 0.3720 0.1927 0.3145 0.117 Uiso 1 1 calc R . .
C10 C 0.5469(3) 0.3483(2) 0.3155(4) 0.0823(10) Uani 1 1 d . . .
H10A H 0.5510 0.4138 0.3161 0.123 Uiso 1 1 calc R . .
H10B H 0.5122 0.3270 0.2194 0.123 Uiso 1 1 calc R . .
H10C H 0.6572 0.3244 0.3560 0.123 Uiso 1 1 calc R . .

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 0.0563(4) 0.0699(4) 0.0302(3) -0.0082(2) 0.0012(2) 0.0247(3)
O1 0.0341(8) 0.0766(11) 0.0379(7) -0.0205(7) -0.0057(6) 0.0192(7)
N1 0.0331(8) 0.0410(9) 0.0321(7) -0.0041(6) 0.0033(6) 0.0079(6)
C1 0.0353(10) 0.0346(9) 0.0319(8) -0.0030(7) 0.0032(7) 0.0037(7)
C2 0.0271(8) 0.0342(9) 0.0318(8) -0.0003(7) 0.0031(7) -0.0021(6)
C3 0.0356(10) 0.0358(10) 0.0397(10) -0.0017(8) 0.0048(8) 0.0033(7)
C4 0.0370(10) 0.0404(11) 0.0407(10) 0.0057(8) -0.0009(8) 0.0017(8)
C5 0.0334(10) 0.0419(10) 0.0348(9) -0.0008(8) 0.0011(7) -0.0091(8)
C5' 0.0569(14) 0.0565(14) 0.0360(10) 0.0015(9) -0.0034(10) -0.0079(11)
C6 0.0349(10) 0.0387(10) 0.0398(10) -0.0091(8) 0.0015(8) -0.0033(8)
C7 0.0349(10) 0.0326(9) 0.0382(9) -0.0033(7) -0.0025(8) 0.0013(7)
C8 0.0351(11) 0.0864(18) 0.0430(11) -0.0262(11) -0.0119(9) 0.0231(11)
C9 0.0501(15) 0.098(2) 0.084(2) 0.0309(18) 0.0121(14) 0.0237(15)
C10 0.0362(13) 0.0707(19) 0.136(3) 0.0030(19) 0.0078(16) 0.0061(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 C1 1.6679(19) . ?
O1 C1 1.312(2) . ?
O1 C8 1.474(2) . ?
N1 C1 1.337(2) . ?
N1 C2 1.424(2) . ?
N1 H1 0.8700 . ?
C2 C7 1.383(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.383(3) . ?
C5 C5' 1.510(3) . ?
C5' H5'1 0.9700 . ?
C5' H5'2 0.9700 . ?
C5' H5'3 0.9700 . ?
C6 C7 1.388(3) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C10 1.481(4) . ?
C8 C9 1.489(4) . ?
C8 H8 0.9900 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?

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
C1 O1 C8 121.11(16) . . ?
C1 N1 C2 129.78(17) . . ?
C1 N1 H1 115.1 . . ?
C2 N1 H1 115.1 . . ?
O1 C1 N1 113.19(16) . . ?
O1 C1 S1 124.90(14) . . ?
N1 C1 S1 121.90(15) . . ?
C7 C2 C3 119.16(17) . . ?
C7 C2 N1 123.89(16) . . ?
C3 C2 N1 116.91(16) . . ?
C2 C3 C4 120.55(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.07(18) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 117.54(18) . . ?
C4 C5 C5' 121.25(19) . . ?
C6 C5 C5' 121.21(19) . . ?
C5 C5' H5'1 109.5 . . ?
C5 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
C5 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C7 C6 C5 122.17(18) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C2 C7 C6 119.44(17) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O1 C8 C10 106.3(2) . . ?
O1 C8 C9 107.1(2) . . ?
C10 C8 C9 114.3(2) . . ?
O1 C8 H8 109.7 . . ?
C10 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.0
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.48
_refine_diff_density_rms         0.061

# Attachment 'B701489A__1.cif'

data_(1)
_database_code_depnum_ccdc_archive 'CCDC 635333'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N O S'
_chemical_formula_sum            'C10 H13 N O S'
_chemical_formula_weight         195.27

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           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.1050(8)
_cell_length_b                   10.9411(10)
_cell_length_c                   11.9874(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.821(2)
_cell_angle_gamma                90
_cell_volume                     1062.90(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2400
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   '(SADABS, Bruker, 2000 & Blessing, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART CCD'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8700
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.5
_diffrn_reflns_theta_max         30.0
_reflns_number_total             3085
_reflns_number_gt                2457
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_structure_solution    'SIR92 (Altomare et al., 1992)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHEXLTL (Bruker, 2000)'

_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^)+(0.0719P)^2^+0.2273P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3085
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.052
_refine_ls_wR_factor_ref         0.139
_refine_ls_wR_factor_gt          0.130
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21321(5) 0.11600(4) 0.46816(4) 0.04251(16) Uani 1 1 d . . .
O1 O 0.11328(14) 0.32051(10) 0.56767(10) 0.0406(3) Uani 1 1 d . . .
N1 N -0.04655(16) 0.15847(12) 0.59139(11) 0.0372(3) Uani 1 1 d . . .
H1 H -0.0670 0.0820 0.5768 0.045 Uiso 1 1 calc R . .
C1 C 0.08937(18) 0.20352(14) 0.54525(13) 0.0337(3) Uani 1 1 d . . .
C2 C -0.16300(19) 0.21734(14) 0.66109(13) 0.0347(3) Uani 1 1 d . . .
C3 C -0.3278(2) 0.18721(18) 0.64492(15) 0.0436(4) Uani 1 1 d . . .
H3 H -0.3597 0.1347 0.5864 0.052 Uiso 1 1 calc R . .
C4 C -0.4452(2) 0.2349(2) 0.71558(17) 0.0558(5) Uani 1 1 d . . .
H4 H -0.5567 0.2131 0.7060 0.067 Uiso 1 1 calc R . .
C5 C -0.3996(3) 0.3139(2) 0.79976(17) 0.0610(6) Uani 1 1 d . . .
H5 H -0.4797 0.3470 0.8471 0.073 Uiso 1 1 calc R . .
C6 C -0.2352(3) 0.3444(2) 0.81425(15) 0.0551(5) Uani 1 1 d . . .
H6 H -0.2041 0.3989 0.8713 0.066 Uiso 1 1 calc R . .
C7 C -0.1160(2) 0.29584(16) 0.74613(14) 0.0420(4) Uani 1 1 d . . .
H7 H -0.0043 0.3159 0.7574 0.050 Uiso 1 1 calc R . .
C8 C 0.2546(2) 0.38685(15) 0.52097(17) 0.0432(4) Uani 1 1 d . . .
H8 H 0.3520 0.3324 0.5184 0.052 Uiso 1 1 calc R . .
C9 C 0.2098(3) 0.4293(2) 0.4055(2) 0.0603(6) Uani 1 1 d . . .
H9A H 0.1915 0.3590 0.3576 0.090 Uiso 1 1 calc R . .
H9B H 0.2990 0.4784 0.3763 0.090 Uiso 1 1 calc R . .
H9C H 0.1100 0.4781 0.4080 0.090 Uiso 1 1 calc R . .
C10 C 0.2864(3) 0.48991(19) 0.6018(2) 0.0689(7) Uani 1 1 d . . .
H10A H 0.3154 0.4566 0.6745 0.103 Uiso 1 1 calc R . .
H10B H 0.1879 0.5396 0.6078 0.103 Uiso 1 1 calc R . .
H10C H 0.3766 0.5399 0.5752 0.103 Uiso 1 1 calc R . .

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 0.0382(2) 0.0311(2) 0.0587(3) -0.00543(17) 0.01711(18) -0.00169(15)
O1 0.0372(6) 0.0281(5) 0.0567(7) -0.0044(5) 0.0109(5) -0.0024(4)
N1 0.0376(7) 0.0297(6) 0.0447(8) -0.0036(5) 0.0109(6) -0.0030(5)
C1 0.0320(7) 0.0297(7) 0.0395(8) -0.0005(6) 0.0033(6) 0.0003(5)
C2 0.0373(8) 0.0334(7) 0.0334(7) 0.0043(6) 0.0067(6) 0.0045(6)
C3 0.0393(8) 0.0497(10) 0.0419(9) 0.0043(7) 0.0064(7) 0.0033(7)
C4 0.0401(9) 0.0720(14) 0.0556(11) 0.0134(10) 0.0118(8) 0.0135(9)
C5 0.0624(13) 0.0729(14) 0.0482(11) 0.0079(10) 0.0232(9) 0.0273(11)
C6 0.0773(14) 0.0548(11) 0.0335(9) -0.0042(8) 0.0096(9) 0.0148(10)
C7 0.0485(9) 0.0426(9) 0.0349(8) 0.0016(7) 0.0031(7) 0.0047(7)
C8 0.0290(7) 0.0307(8) 0.0703(12) 0.0010(7) 0.0057(7) -0.0030(6)
C9 0.0456(10) 0.0530(11) 0.0825(15) 0.0221(11) 0.0097(10) -0.0005(9)
C10 0.0476(11) 0.0434(11) 0.116(2) -0.0238(12) 0.0053(12) -0.0081(9)

_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 C1 1.6749(16) . ?
O1 C1 1.3216(19) . ?
O1 C8 1.4730(19) . ?
N1 C1 1.3341(19) . ?
N1 C2 1.4236(19) . ?
N1 H1 0.8700 . ?
C2 C7 1.382(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.380(2) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.499(3) . ?
C8 C10 1.506(3) . ?
C8 H8 0.9900 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?

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
C1 O1 C8 120.83(12) . . ?
C1 N1 C2 129.38(14) . . ?
C1 N1 H1 115.3 . . ?
C2 N1 H1 115.3 . . ?
O1 C1 N1 113.15(13) . . ?
O1 C1 S1 125.35(12) . . ?
N1 C1 S1 121.49(12) . . ?
C7 C2 C3 120.35(15) . . ?
C7 C2 N1 122.42(15) . . ?
C3 C2 N1 117.12(15) . . ?
C2 C3 C4 119.58(18) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.40(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.47(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 120.97(19) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C2 C7 C6 119.20(18) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
O1 C8 C9 108.93(15) . . ?
O1 C8 C10 104.57(16) . . ?
C9 C8 C10 113.49(17) . . ?
O1 C8 H8 109.9 . . ?
C9 C8 H8 109.9 . . ?
C10 C8 H8 109.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.0
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.063

# Attachment 'B701489A__2.cif'

data_(2)
_database_code_depnum_ccdc_archive 'CCDC 635334'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 Cl N O S'
_chemical_formula_sum            'C10 H12 Cl N O S'
_chemical_formula_weight         229.72

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   P21/c

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

_cell_length_a                   7.1307(6)
_cell_length_b                   19.8847(17)
_cell_length_c                   8.2842(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.827(1)
_cell_angle_gamma                90
_cell_volume                     1157.40(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2.3
_cell_measurement_theta_min      28.1
_cell_measurement_theta_max      2701

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   '(SADABS, Bruker, 2000 & Blessing, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART CCD'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9569
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.7
_diffrn_reflns_theta_max         30.0
_reflns_number_total             3362
_reflns_number_gt                2590
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_structure_solution    'SIR92 (Altomare et al., 1992)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHEXLTL (Bruker, 2000)'

_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^)+(0.0683P)^2^+0.0786P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3362
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.044
_refine_ls_wR_factor_ref         0.121
_refine_ls_wR_factor_gt          0.113
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_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
Cl1 Cl 0.78250(6) 0.10053(2) -0.48149(6) 0.05135(15) Uani 1 1 d . . .
S1 S 0.03003(6) 0.07367(2) 0.20298(4) 0.03969(14) Uani 1 1 d . . .
O1 O 0.28826(17) 0.15361(5) 0.10328(13) 0.0399(3) Uani 1 1 d . . .
N1 N 0.21903(18) 0.06110(6) -0.04274(15) 0.0340(3) Uani 1 1 d . . .
H1 H 0.1477 0.0257 -0.0660 0.041 Uiso 1 1 calc R . .
C1 C 0.1856(2) 0.09785(7) 0.08476(17) 0.0306(3) Uani 1 1 d . . .
C2 C 0.3569(2) 0.07290(6) -0.14452(17) 0.0294(3) Uani 1 1 d . . .
C3 C 0.3020(2) 0.06494(7) -0.31247(18) 0.0338(3) Uani 1 1 d . . .
H3 H 0.1751 0.0541 -0.3558 0.041 Uiso 1 1 calc R . .
C4 C 0.4333(2) 0.07281(8) -0.41660(19) 0.0356(3) Uani 1 1 d . . .
H4 H 0.3967 0.0669 -0.5302 0.043 Uiso 1 1 calc R . .
C5 C 0.6184(2) 0.08950(7) -0.35121(18) 0.0347(3) Uani 1 1 d . . .
C6 C 0.6752(2) 0.09681(8) -0.18408(19) 0.0369(3) Uani 1 1 d . . .
H6 H 0.8023 0.1076 -0.1412 0.044 Uiso 1 1 calc R . .
C7 C 0.5452(2) 0.08823(7) -0.08062(18) 0.0337(3) Uani 1 1 d . . .
H7 H 0.5836 0.0927 0.0332 0.040 Uiso 1 1 calc R . .
C8 C 0.2663(3) 0.20223(8) 0.2326(2) 0.0460(4) Uani 1 1 d . . .
H8 H 0.2412 0.1780 0.3312 0.055 Uiso 1 1 calc R . .
C9 C 0.1037(4) 0.24853(11) 0.1719(3) 0.0695(6) Uani 1 1 d . . .
H9A H -0.0140 0.2230 0.1518 0.104 Uiso 1 1 calc R . .
H9B H 0.1243 0.2697 0.0709 0.104 Uiso 1 1 calc R . .
H9C H 0.0954 0.2828 0.2537 0.104 Uiso 1 1 calc R . .
C10 C 0.4555(4) 0.23732(11) 0.2701(3) 0.0679(6) Uani 1 1 d . . .
H10A H 0.5539 0.2049 0.3105 0.102 Uiso 1 1 calc R . .
H10B H 0.4508 0.2715 0.3527 0.102 Uiso 1 1 calc R . .
H10C H 0.4839 0.2582 0.1712 0.102 Uiso 1 1 calc R . .

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
Cl1 0.0423(2) 0.0622(3) 0.0553(3) 0.00095(19) 0.0246(2) -0.00199(18)
S1 0.0413(2) 0.0483(2) 0.0318(2) -0.00644(15) 0.01276(16) -0.01028(16)
O1 0.0527(7) 0.0305(5) 0.0399(6) -0.0081(4) 0.0175(5) -0.0082(5)
N1 0.0350(7) 0.0324(6) 0.0373(6) -0.0078(5) 0.0135(5) -0.0077(5)
C1 0.0317(7) 0.0312(7) 0.0290(6) -0.0003(5) 0.0053(5) -0.0002(5)
C2 0.0300(7) 0.0244(6) 0.0348(7) -0.0014(5) 0.0087(5) 0.0003(5)
C3 0.0273(7) 0.0366(7) 0.0375(7) -0.0064(6) 0.0060(6) -0.0003(5)
C4 0.0347(8) 0.0393(8) 0.0334(7) -0.0035(6) 0.0079(6) 0.0028(6)
C5 0.0308(7) 0.0328(7) 0.0427(8) 0.0010(6) 0.0127(6) 0.0034(6)
C6 0.0258(7) 0.0404(8) 0.0440(8) -0.0013(6) 0.0045(6) 0.0008(6)
C7 0.0317(7) 0.0352(7) 0.0335(7) 0.0003(5) 0.0033(6) 0.0025(6)
C8 0.0752(12) 0.0304(7) 0.0350(7) -0.0063(6) 0.0165(8) -0.0042(8)
C9 0.1012(19) 0.0474(10) 0.0651(12) -0.0007(9) 0.0295(12) 0.0207(11)
C10 0.0963(18) 0.0458(11) 0.0609(12) -0.0153(9) 0.0114(12) -0.0244(11)

_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
Cl1 C5 1.7361(15) . ?
S1 C1 1.6708(15) . ?
O1 C1 1.3231(17) . ?
O1 C8 1.4711(18) . ?
N1 C1 1.3388(18) . ?
N1 C2 1.4197(18) . ?
N1 H1 0.8700 . ?
C2 C3 1.389(2) . ?
C2 C7 1.390(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.382(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.499(3) . ?
C8 C10 1.503(3) . ?
C8 H8 0.9900 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?

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
C1 O1 C8 120.64(12) . . ?
C1 N1 C2 127.81(12) . . ?
C1 N1 H1 116.1 . . ?
C2 N1 H1 116.1 . . ?
O1 C1 N1 112.29(12) . . ?
O1 C1 S1 125.65(11) . . ?
N1 C1 S1 122.06(11) . . ?
C3 C2 C7 119.68(14) . . ?
C3 C2 N1 118.10(13) . . ?
C7 C2 N1 122.12(13) . . ?
C4 C3 C2 120.40(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.04(14) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.09(14) . . ?
C4 C5 Cl1 119.19(12) . . ?
C6 C5 Cl1 119.71(12) . . ?
C7 C6 C5 119.79(14) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 119.97(14) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O1 C8 C9 109.38(15) . . ?
O1 C8 C10 104.60(15) . . ?
C9 C8 C10 113.57(17) . . ?
O1 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
C10 C8 H8 109.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.0
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.065


