# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Andreas Lemmerer'
_publ_contact_author_email       ANDREAS.LEMMERER@GMAIL.COM

_publ_section_title              
;
The influence of substitution and weak interactions
on the crystal structures of a series of 2,6-disubstituted N-arylthioamides
;
_publ_requested_category         FO
loop_
_publ_author_name
'Andreas Lemmerer'
'Manuel A Fernandes'
'Marcus Layh'
'Demetrius C Levendis'
'Bernard Omondi'

# Attachment 'Thioamide_cif.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2009-03-02 at 17:13:20
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : 6bbo13_s smart

data_1
_database_code_depnum_ccdc_archive 'CCDC 710584'

_audit_creation_date             2009-03-02T17:13:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2,6-diflourophenylthioamide
;
_chemical_formula_moiety         'C7 H5 F2 N S'
_chemical_formula_sum            'C7 H5 F2 N S'
_chemical_formula_weight         173.18

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.346(1)
_cell_length_b                   8.119(1)
_cell_length_c                   17.883(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1502.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    820
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      24.82

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
absorption corrections were made using the program SADABS
(Sheldrick, 1996).

;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  0.947

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_number            14956
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             1813
_reflns_number_gt                1079
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_reduction        'Bruker SAINT+'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0531P)²+0.9667P] 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_number_reflns         1813
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.042
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.36
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
F F 0.0171 0.0103 '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'

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 0.4484(2) 0.0116(3) 0.62859(12) 0.0326(6) Uani 1 1 d . . .
C2 C 0.3852(3) 0.0983(3) 0.57202(15) 0.0428(7) Uani 1 1 d . . .
C3 C 0.2523(3) 0.1015(4) 0.5662(2) 0.0598(9) Uani 1 1 d . . .
H3 H 0.211 0.1604 0.527 0.072 Uiso 1 1 calc R . .
C4 C 0.1807(3) 0.0163(4) 0.6190(2) 0.0682(12) Uani 1 1 d . . .
H4 H 0.089 0.0175 0.6159 0.082 Uiso 1 1 calc R . .
C5 C 0.2393(3) -0.0703(4) 0.67618(19) 0.0572(9) Uani 1 1 d . . .
H5 H 0.189 -0.1266 0.7125 0.069 Uiso 1 1 calc R . .
C6 C 0.3714(3) -0.0732(3) 0.67932(15) 0.0420(7) Uani 1 1 d . . .
C7 C 0.6650(2) 0.1269(3) 0.63105(12) 0.0318(5) Uani 1 1 d . . .
H7 H 0.6288 0.2344 0.6294 0.038 Uiso 1 1 calc R . .
N1 N 0.58474(19) 0.0000(3) 0.63262(11) 0.0304(5) Uani 1 1 d . . .
F1 F 0.45934(16) 0.1806(2) 0.52181(8) 0.0549(5) Uani 1 1 d . . .
F2 F 0.43284(16) -0.1617(2) 0.73269(9) 0.0534(5) Uani 1 1 d . . .
S1 S 0.82396(6) 0.10992(8) 0.63171(4) 0.0432(2) Uani 1 1 d . . .
H1 H 0.617(3) -0.102(4) 0.6348(15) 0.052 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0288(12) 0.0314(14) 0.0377(12) -0.0108(11) 0.0011(10) 0.0023(10)
C2 0.0399(15) 0.0399(16) 0.0485(15) -0.0164(13) -0.0073(12) 0.0100(13)
C3 0.0429(17) 0.055(2) 0.081(2) -0.0337(18) -0.0252(17) 0.0200(16)
C4 0.0260(15) 0.062(2) 0.117(3) -0.053(2) -0.0033(18) 0.0029(16)
C5 0.0354(16) 0.056(2) 0.081(2) -0.0352(17) 0.0157(16) -0.0073(14)
C6 0.0357(14) 0.0402(16) 0.0502(16) -0.0179(12) 0.0078(12) -0.0043(12)
C7 0.0302(12) 0.0324(13) 0.0327(12) 0.0039(10) 0.0035(10) 0.0041(11)
N1 0.0279(10) 0.0259(11) 0.0375(10) 0.0021(9) 0.0022(9) 0.0013(9)
F1 0.0641(11) 0.0546(11) 0.0460(9) 0.0048(8) -0.0079(8) 0.0169(9)
F2 0.0556(10) 0.0554(10) 0.0492(9) 0.0049(7) 0.0136(8) -0.0094(8)
S1 0.0284(3) 0.0324(4) 0.0687(5) 0.0072(3) 0.0051(3) -0.0016(3)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.390(4) . ?
C1 C2 1.395(3) . ?
C1 N1 1.415(3) . ?
C2 F1 1.357(3) . ?
C2 C3 1.379(4) . ?
C3 C4 1.386(5) . ?
C3 H3 0.95 . ?
C4 C5 1.380(5) . ?
C4 H4 0.95 . ?
C5 C6 1.368(4) . ?
C5 H5 0.95 . ?
C6 F2 1.354(3) . ?
C7 N1 1.323(3) . ?
C7 S1 1.651(2) . ?
C7 H7 0.95 . ?
N1 H1 0.89(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.0(2) . . ?
C6 C1 N1 120.3(2) . . ?
C2 C1 N1 122.5(2) . . ?
F1 C2 C3 120.3(3) . . ?
F1 C2 C1 117.6(2) . . ?
C3 C2 C1 122.1(3) . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
F2 C6 C5 120.5(3) . . ?
F2 C6 C1 117.0(2) . . ?
C5 C6 C1 122.5(3) . . ?
N1 C7 S1 124.1(2) . . ?
N1 C7 H7 118 . . ?
S1 C7 H7 118 . . ?
C7 N1 C1 124.9(2) . . ?
C7 N1 H1 119(2) . . ?
C1 N1 H1 116(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -179.5(2) . . . . ?
N1 C1 C2 F1 -3.4(3) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
N1 C1 C2 C3 176.3(2) . . . . ?
F1 C2 C3 C4 -179.7(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 F2 -177.5(2) . . . . ?
C4 C5 C6 C1 2.0(4) . . . . ?
C2 C1 C6 F2 177.9(2) . . . . ?
N1 C1 C6 F2 1.7(3) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
N1 C1 C6 C5 -177.7(2) . . . . ?
S1 C7 N1 C1 -176.91(18) . . . . ?
C6 C1 N1 C7 -131.6(2) . . . . ?
C2 C1 N1 C7 52.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 S1 0.95 2.86 3.775(3) 163 1_455
N1 H1 S1 0.89(3) 2.42(3) 3.305(2) 172(3) 7_755
C7 H7 S1 0.95 3.09 3.924(3) 148 7_765
_chemical_name_common            2,6-diflourophenylthioamide

###END

data_2
_database_code_depnum_ccdc_archive 'CCDC 710585'

_audit_creation_date             2009-03-02T17:18:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2,6-dichlorophenylthioamide
;
_chemical_formula_moiety         'C7 H5 Cl2 N S'
_chemical_formula_sum            'C7 H5 Cl2 N S'
_chemical_formula_weight         206.08

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.873(2)
_cell_length_b                   15.643(4)
_cell_length_c                   7.991(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.336(5)
_cell_angle_gamma                90
_cell_volume                     874.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    721
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.24

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_special_details           
;
absorption corrections were made using the program SADABS
(Sheldrick, 1996).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7717
_exptl_absorpt_correction_T_max  0.8831

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_number            5989
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.6
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2116
_reflns_number_gt                1583
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_reduction        'Bruker SAINT+'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0296P)²+0.2418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0125(13)
_refine_ls_number_reflns         2116
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0734
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.7859(2) 0.44320(10) 0.0431(2) 0.0306(3) Uani 1 1 d . . .
C2 C 0.9491(2) 0.46008(11) 0.2119(2) 0.0363(4) Uani 1 1 d . . .
C3 C 1.0049(3) 0.54275(13) 0.2718(3) 0.0469(5) Uani 1 1 d . . .
H3 H 1.1141 0.5531 0.389 0.056 Uiso 1 1 calc R . .
C4 C 0.9016(3) 0.61021(13) 0.1611(3) 0.0501(5) Uani 1 1 d . . .
H4 H 0.9394 0.6671 0.2035 0.06 Uiso 1 1 calc R . .
C5 C 0.7440(3) 0.59640(11) -0.0109(3) 0.0416(4) Uani 1 1 d . . .
H5 H 0.6759 0.6431 -0.0888 0.05 Uiso 1 1 calc R . .
C6 C 0.6872(2) 0.51288(11) -0.0674(2) 0.0339(4) Uani 1 1 d . . .
C7 C 0.6859(2) 0.30240(11) 0.0864(2) 0.0348(4) Uani 1 1 d . . .
H7 H 0.7091 0.3201 0.2088 0.042 Uiso 1 1 calc R . .
N1 N 0.7206(2) 0.35911(9) -0.0180(2) 0.0334(3) Uani 1 1 d . . .
S1 S 0.60652(8) 0.20458(3) 0.02310(7) 0.04621(16) Uani 1 1 d . . .
Cl1 Cl 1.09108(7) 0.37708(3) 0.34965(7) 0.05224(16) Uani 1 1 d . . .
Cl2 Cl 0.48911(7) 0.49385(3) -0.28080(7) 0.04748(15) Uani 1 1 d . . .
H1 H 0.696(3) 0.3458(14) -0.130(3) 0.057 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0371(9) 0.0303(8) 0.0291(8) -0.0015(6) 0.0191(7) 0.0002(7)
C2 0.0364(9) 0.0395(10) 0.0331(9) -0.0004(7) 0.0162(8) 0.0004(8)
C3 0.0433(11) 0.0489(12) 0.0452(11) -0.0123(9) 0.0175(9) -0.0093(9)
C4 0.0568(13) 0.0350(10) 0.0641(14) -0.0118(9) 0.0325(11) -0.0099(9)
C5 0.0485(11) 0.0297(9) 0.0538(12) 0.0013(8) 0.0298(10) 0.0031(8)
C6 0.0385(10) 0.0341(9) 0.0332(9) 0.0011(7) 0.0199(8) 0.0018(7)
C7 0.0393(10) 0.0355(9) 0.0294(8) 0.0017(7) 0.0158(8) 0.0032(7)
N1 0.0444(8) 0.0287(7) 0.0264(7) -0.0011(6) 0.0157(7) 0.0003(6)
S1 0.0650(3) 0.0304(2) 0.0409(3) 0.00068(19) 0.0222(2) -0.0049(2)
Cl1 0.0467(3) 0.0554(3) 0.0411(3) 0.0073(2) 0.0085(2) 0.0075(2)
Cl2 0.0530(3) 0.0458(3) 0.0338(2) 0.00488(19) 0.0114(2) 0.0094(2)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.393(2) . ?
C1 C2 1.396(2) . ?
C1 N1 1.415(2) . ?
C2 C3 1.379(3) . ?
C2 Cl1 1.737(2) . ?
C3 C4 1.377(3) . ?
C3 H3 0.95 . ?
C4 C5 1.382(3) . ?
C4 H4 0.95 . ?
C5 C6 1.388(2) . ?
C5 H5 0.95 . ?
C6 Cl2 1.728(2) . ?
C7 N1 1.330(2) . ?
C7 S1 1.643(2) . ?
C7 H7 0.95 . ?
N1 H1 0.85(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.6(2) . . ?
C6 C1 N1 120.0(2) . . ?
C2 C1 N1 122.5(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 Cl1 118.1(2) . . ?
C1 C2 Cl1 120.7(1) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 121.9(2) . . ?
C5 C6 Cl2 119.6(1) . . ?
C1 C6 Cl2 118.6(1) . . ?
N1 C7 S1 125.9(1) . . ?
N1 C7 H7 117 . . ?
S1 C7 H7 117 . . ?
C7 N1 C1 123.4(1) . . ?
C7 N1 H1 118.8(2) . . ?
C1 N1 H1 117.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 3.2(3) . . . . ?
N1 C1 C2 C3 -177.28(16) . . . . ?
C6 C1 C2 Cl1 -175.07(12) . . . . ?
N1 C1 C2 Cl1 4.4(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
Cl1 C2 C3 C4 176.43(15) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 Cl2 179.39(14) . . . . ?
C2 C1 C6 C5 -1.9(2) . . . . ?
N1 C1 C6 C5 178.66(16) . . . . ?
C2 C1 C6 Cl2 177.92(13) . . . . ?
N1 C1 C6 Cl2 -1.6(2) . . . . ?
S1 C7 N1 C1 178.84(13) . . . . ?
C6 C1 N1 C7 -126.38(18) . . . . ?
C2 C1 N1 C7 54.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.85(2) 2.65(2) 3.496(2) 176(2) 4_565
C7 H7 S1 0.95 3 3.819(2) 146 4_566
_chemical_name_common            2,6-dichlorophenylthioamide

###END

data_3
_database_code_depnum_ccdc_archive 'CCDC 710586'

_audit_creation_date             2009-03-02T17:31:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2,6-dibromophenylthioamide
;
_chemical_formula_moiety         'C7 H5 Br2 N S'
_chemical_formula_sum            'C7 H5 Br2 N S'
_chemical_formula_weight         295

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9801(5)
_cell_length_b                   8.0314(5)
_cell_length_c                   14.5984(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.884(4)
_cell_angle_gamma                90
_cell_volume                     921.74(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1851
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.12

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_special_details           
;
absorption corrections were made using the program SADABS
(Sheldrick, 1996).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.134
_exptl_absorpt_correction_T_max  0.70

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_number            6607
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2216
_reflns_number_gt                1620
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_reduction        'Bruker SAINT+'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0614P)²+0.7396P] 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_number_reflns         2216
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.131
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.124

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.3583(6) 0.6488(5) 0.8837(3) 0.0345(10) Uani 1 1 d . . .
C2 C 0.3733(7) 0.7426(6) 0.9646(3) 0.0406(11) Uani 1 1 d . . .
C3 C 0.5296(8) 0.7821(6) 1.0154(3) 0.0488(13) Uani 1 1 d . . .
H3 H 0.5373 0.8491 1.0696 0.059 Uiso 1 1 calc R . .
C4 C 0.6765(7) 0.7235(7) 0.9868(3) 0.0485(13) Uani 1 1 d . . .
H4 H 0.785 0.752 1.021 0.058 Uiso 1 1 calc R . .
C5 C 0.6648(7) 0.6252(6) 0.9099(3) 0.0438(11) Uani 1 1 d . . .
H5 H 0.7649 0.583 0.8912 0.053 Uiso 1 1 calc R . .
C6 C 0.5068(6) 0.5872(5) 0.8593(3) 0.0332(9) Uani 1 1 d . . .
C7 C 0.0962(6) 0.7311(6) 0.7866(3) 0.0379(10) Uani 1 1 d . . .
H7 H 0.1314 0.8432 0.7983 0.045 Uiso 1 1 calc R . .
N1 N 0.1981(5) 0.6137(5) 0.8282(3) 0.0378(9) Uani 1 1 d . . .
S1 S -0.08510(18) 0.70127(16) 0.71658(10) 0.0493(3) Uani 1 1 d . . .
Br1 Br 0.17902(9) 0.81414(8) 1.01199(5) 0.0646(2) Uani 1 1 d . . .
Br2 Br 0.49267(7) 0.45272(7) 0.75278(3) 0.0514(2) Uani 1 1 d . . .
H1 H 0.170(8) 0.499(7) 0.816(4) 0.062 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.041(3) 0.026(2) 0.037(2) 0.0032(17) 0.0054(19) -0.0026(19)
C2 0.048(3) 0.037(2) 0.039(2) 0.0002(19) 0.012(2) 0.002(2)
C3 0.061(4) 0.047(3) 0.036(2) -0.003(2) 0.000(2) -0.006(3)
C4 0.044(3) 0.057(3) 0.039(2) 0.007(2) -0.009(2) -0.010(3)
C5 0.037(3) 0.048(3) 0.046(3) 0.011(2) 0.006(2) -0.001(2)
C6 0.041(3) 0.028(2) 0.031(2) 0.0031(16) 0.0063(18) 0.0013(19)
C7 0.033(2) 0.035(2) 0.045(2) -0.0005(19) 0.0046(19) 0.000(2)
N1 0.033(2) 0.0288(19) 0.049(2) -0.0022(17) 0.0002(17) -0.0009(17)
S1 0.0391(7) 0.0465(7) 0.0572(8) 0.0026(6) -0.0060(6) 0.0020(6)
Br1 0.0609(4) 0.0684(4) 0.0700(4) -0.0183(3) 0.0268(3) 0.0032(3)
Br2 0.0556(4) 0.0477(3) 0.0531(3) -0.0147(2) 0.0154(2) -0.0017(2)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.385(6) . ?
C1 C2 1.389(6) . ?
C1 N1 1.420(6) . ?
C2 C3 1.374(7) . ?
C2 Br1 1.892(5) . ?
C3 C4 1.392(8) . ?
C3 H3 0.95 . ?
C4 C5 1.363(7) . ?
C4 H4 0.95 . ?
C5 C6 1.382(7) . ?
C5 H5 0.95 . ?
C6 Br2 1.881(4) . ?
C7 N1 1.323(6) . ?
C7 S1 1.639(5) . ?
C7 H7 0.95 . ?
N1 H1 0.96(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
C6 C1 C2 117.4(4) . . ?
C6 C1 N1 120.6(4) . . ?
C2 C1 N1 122.1(4) . . ?
C3 C2 C1 121.4(5) . . ?
C3 C2 Br1 117.3(4) . . ?
C1 C2 Br1 121.3(4) . . ?
C2 C3 C4 119.6(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.8(4) . . ?
C5 C6 Br2 119.2(4) . . ?
C1 C6 Br2 119.0(3) . . ?
N1 C7 S1 126.1(4) . . ?
N1 C7 H7 117 . . ?
S1 C7 H7 117 . . ?
C7 N1 C1 122.9(4) . . ?
C7 N1 H1 120(4) . . ?
C1 N1 H1 117(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 4.2(7) . . . . ?
N1 C1 C2 C3 -176.9(4) . . . . ?
C6 C1 C2 Br1 -173.5(3) . . . . ?
N1 C1 C2 Br1 5.5(6) . . . . ?
C1 C2 C3 C4 -1.8(8) . . . . ?
Br1 C2 C3 C4 175.9(4) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C4 C5 C6 C1 1.1(7) . . . . ?
C4 C5 C6 Br2 179.5(4) . . . . ?
C2 C1 C6 C5 -3.8(6) . . . . ?
N1 C1 C6 C5 177.2(4) . . . . ?
C2 C1 C6 Br2 177.7(3) . . . . ?
N1 C1 C6 Br2 -1.2(5) . . . . ?
S1 C7 N1 C1 176.2(4) . . . . ?
C6 C1 N1 C7 -118.6(5) . . . . ?
C2 C1 N1 C7 62.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.96(6) 2.51(6) 3.465(4) 178(5) 2_546
C7 H7 S1 0.95 2.9 3.777(5) 154 2_556
C4 H4 S1 0.95 2.89 3.612(5) 134 4_676
_chemical_name_common            2,6-dibromophenylthioamide

###END

data_4
_database_code_depnum_ccdc_archive 'CCDC 710587'

_audit_creation_date             2009-03-02T17:41:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2,6-dimethylphenylthioamide
;
_chemical_formula_moiety         'C9 H11 N S'
_chemical_formula_sum            'C9 H11 N S'
_chemical_formula_weight         165.25

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.555(2)
_cell_length_b                   8.0597(13)
_cell_length_c                   16.133(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.422(4)
_cell_angle_gamma                90
_cell_volume                     1855.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    628
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      23.064

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
absorption corrections were made using the program SADABS
(Sheldrick, 1996).

;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.8775
_exptl_absorpt_correction_T_max  0.9831

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_number            6215
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2230
_reflns_number_gt                1253
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_reduction        'Bruker SAINT+'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0502P)²+0.3281P] 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_number_reflns         2230
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.87318(15) 0.3543(2) 0.43529(12) 0.0369(5) Uani 1 1 d . . .
C2 C 0.95664(16) 0.2655(3) 0.44578(14) 0.0486(6) Uani 1 1 d . . .
C3 C 1.00356(18) 0.2357(3) 0.52854(16) 0.0616(7) Uani 1 1 d . . .
H3 H 1.0601 0.1735 0.5382 0.074 Uiso 1 1 calc R . .
C4 C 0.96929(19) 0.2950(4) 0.59623(15) 0.0646(7) Uani 1 1 d . . .
H4 H 1.0024 0.2736 0.6521 0.077 Uiso 1 1 calc R . .
C5 C 0.88768(18) 0.3850(3) 0.58382(14) 0.0530(6) Uani 1 1 d . . .
H5 H 0.8652 0.426 0.6313 0.064 Uiso 1 1 calc R . .
C6 C 0.83757(15) 0.4169(2) 0.50304(13) 0.0416(5) Uani 1 1 d . . .
C7 C 0.78263(15) 0.2700(2) 0.29856(12) 0.0413(5) Uani 1 1 d . . .
H7 H 0.7933 0.1585 0.317 0.05 Uiso 1 1 calc R . .
C8 C 0.99817(19) 0.2065(3) 0.37220(17) 0.0673(7) Uani 1 1 d . . .
H8A H 1.0647 0.1804 0.392 0.101 Uiso 1 1 calc R . .
H8B H 0.9649 0.1069 0.3476 0.101 Uiso 1 1 calc R . .
H8C H 0.9919 0.2939 0.3292 0.101 Uiso 1 1 calc R . .
C9 C 0.74690(17) 0.5114(3) 0.48892(14) 0.0555(6) Uani 1 1 d . . .
H9A H 0.7322 0.5419 0.5436 0.083 Uiso 1 1 calc R . .
H9B H 0.6965 0.4418 0.4576 0.083 Uiso 1 1 calc R . .
H9C H 0.7528 0.6121 0.4563 0.083 Uiso 1 1 calc R . .
N1 N 0.82099(14) 0.3862(2) 0.35155(10) 0.0416(5) Uani 1 1 d . . .
S1 S 0.71810(5) 0.29777(7) 0.20357(4) 0.0585(2) Uani 1 1 d . . .
H1 H 0.8096(18) 0.486(3) 0.3379(15) 0.07 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0446(13) 0.0305(10) 0.0342(11) 0.0010(8) 0.0044(10) -0.0035(9)
C2 0.0501(14) 0.0465(13) 0.0482(13) 0.0021(10) 0.0073(12) -0.0040(11)
C3 0.0485(15) 0.0705(18) 0.0601(15) 0.0092(13) -0.0026(13) 0.0021(13)
C4 0.0633(17) 0.0812(19) 0.0413(13) 0.0063(13) -0.0089(12) -0.0125(16)
C5 0.0634(18) 0.0568(15) 0.0373(12) -0.0033(11) 0.0068(12) -0.0126(13)
C6 0.0502(14) 0.0346(11) 0.0395(12) -0.0023(9) 0.0081(11) -0.0091(10)
C7 0.0544(14) 0.0302(10) 0.0385(11) 0.0008(9) 0.0073(10) -0.0014(10)
C8 0.0606(17) 0.0721(18) 0.0725(17) -0.0015(14) 0.0212(15) 0.0126(14)
C9 0.0696(17) 0.0447(13) 0.0551(15) -0.0035(11) 0.0194(13) 0.0046(12)
N1 0.0583(12) 0.0284(9) 0.0346(9) 0.0006(8) 0.0011(8) 0.0011(9)
S1 0.0860(5) 0.0411(3) 0.0398(3) -0.0005(3) -0.0083(3) -0.0040(3)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C2 1.391(3) . ?
C1 C6 1.394(3) . ?
C1 N1 1.436(2) . ?
C2 C3 1.395(3) . ?
C2 C8 1.511(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.95 . ?
C4 C5 1.372(4) . ?
C4 H4 0.95 . ?
C5 C6 1.386(3) . ?
C5 H5 0.95 . ?
C6 C9 1.501(3) . ?
C7 N1 1.315(3) . ?
C7 S1 1.646(2) . ?
C7 H7 0.95 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
N1 H1 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.84(19) . . ?
C2 C1 N1 119.55(18) . . ?
C6 C1 N1 117.60(18) . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 C8 122.8(2) . . ?
C3 C2 C8 120.1(2) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 117.5(2) . . ?
C5 C6 C9 121.3(2) . . ?
C1 C6 C9 121.13(19) . . ?
N1 C7 S1 126.8(2) . . ?
N1 C7 H7 116.6 . . ?
S1 C7 H7 116.6 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 N1 C1 124.1(2) . . ?
C7 N1 H1 118.3(2) . . ?
C1 N1 H1 117.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.9(3) . . . . ?
N1 C1 C2 C3 -178.94(19) . . . . ?
C6 C1 C2 C8 -176.2(2) . . . . ?
N1 C1 C2 C8 2.9(3) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C8 C2 C3 C4 176.9(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C9 178.4(2) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
N1 C1 C6 C5 179.56(18) . . . . ?
C2 C1 C6 C9 -179.7(2) . . . . ?
N1 C1 C6 C9 1.2(3) . . . . ?
S1 C7 N1 C1 177.06(17) . . . . ?
C2 C1 N1 C7 63.9(3) . . . . ?
C6 C1 N1 C7 -116.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.84(3) 2.61(3) 3.452(2) 178(2) 4_655
C7 H7 S1 0.95 2.93 3.807(2) 154 4_645
C9 H9A S1 0.98 2.93 3.887(2) 166 6_566
_chemical_name_common            2,6-dimethylphenylthioamide

###END

data_5
_database_code_depnum_ccdc_archive 'CCDC 710588'

_audit_creation_date             2009-03-02T17:45:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2-chloro-6-methylphenylthioamide
;
_chemical_formula_moiety         'C8 H8 Cl N S'
_chemical_formula_sum            'C8 H8 Cl N S'
_chemical_formula_weight         185.66

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.3670(10)
_cell_length_b                   8.0220(10)
_cell_length_c                   16.0680(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.9200(10)
_cell_angle_gamma                90
_cell_volume                     1818.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5886
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.16

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Irregular
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_special_details           
;
absorption corrections were made using the program SADABS
(Sheldrick, 1996).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  0.9658

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.017
_diffrn_reflns_number            15652
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2197
_reflns_number_gt                1778
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_reduction        'Bruker SAINT+'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0625P)²+2.2992P] 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_number_reflns         2197
_refine_ls_number_parameters     105
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.87420(14) 0.3542(2) 0.43580(12) 0.0376(4) Uani 1 1 d D A .
C2 C 0.95805(15) 0.2660(2) 0.44961(12) 0.0470(5) Uani 1 1 d D . .
C3 C 1.00633(18) 0.2362(3) 0.53071(18) 0.0604(7) Uani 1 1 d D A .
H3 H 1.0639 0.1747 0.5396 0.072 Uiso 1 1 calc R . .
C4 C 0.9710(2) 0.2956(4) 0.59882(16) 0.0621(7) Uani 1 1 d D . .
H4 H 1.0037 0.2734 0.6548 0.075 Uiso 1 1 calc R A .
C5 C 0.88852(18) 0.3871(3) 0.58624(14) 0.0526(6) Uani 1 1 d D A .
H5 H 0.8651 0.4311 0.6332 0.063 Uiso 1 1 calc R . .
C6 C 0.84055(11) 0.4140(2) 0.50507(13) 0.0413(5) Uani 1 1 d D . .
C7 C 0.78639(16) 0.2658(3) 0.29918(13) 0.0406(5) Uani 1 1 d . A .
H7 H 0.7996 0.154 0.3171 0.049 Uiso 1 1 calc R . .
N1 N 0.82132(14) 0.3844(2) 0.35258(11) 0.0406(4) Uani 1 1 d . . .
S1 S 0.72178(6) 0.29378(8) 0.20399(4) 0.0577(2) Uani 1 1 d . . .
Cl1A Cl 1.00817(16) 0.1930(2) 0.36563(12) 0.0604(3) Uani 0.5 1 d PD A 1
C8A C 0.7540(5) 0.5115(11) 0.4864(5) 0.0604(3) Uani 0.5 1 d PD A 1
H8A H 0.7288 0.5272 0.5384 0.091 Uiso 0.5 1 calc PR A 1
H8B H 0.7071 0.4526 0.4443 0.091 Uiso 0.5 1 calc PR A 1
H8C H 0.7677 0.6203 0.4638 0.091 Uiso 0.5 1 calc PR A 1
C8B C 0.9990(7) 0.2149(11) 0.3751(5) 0.0604(3) Uani 0.5 1 d PD A 2
H8D H 0.9739 0.2868 0.3267 0.091 Uiso 0.5 1 calc PR A 2
H8E H 0.982 0.0988 0.3606 0.091 Uiso 0.5 1 calc PR A 2
H8F H 1.0682 0.2255 0.3889 0.091 Uiso 0.5 1 calc PR A 2
Cl1B Cl 0.73367(11) 0.5231(2) 0.49008(12) 0.0604(3) Uani 0.5 1 d PD A 2
H1 H 0.811(2) 0.486(4) 0.341(2) 0.072 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0455(11) 0.0315(9) 0.0342(9) 0.0013(8) 0.0039(8) -0.0037(8)
C2 0.0472(12) 0.0473(12) 0.0461(12) 0.0005(10) 0.0076(10) -0.0004(10)
C3 0.0468(14) 0.0720(18) 0.0577(14) 0.0088(13) -0.0018(11) 0.0057(12)
C4 0.0607(16) 0.079(2) 0.0407(12) 0.0068(12) -0.0057(11) -0.0074(14)
C5 0.0624(15) 0.0593(15) 0.0357(11) -0.0039(10) 0.0082(10) -0.0138(12)
C6 0.0490(12) 0.0351(10) 0.0394(10) -0.0010(9) 0.0074(9) -0.0069(9)
C7 0.0526(12) 0.0307(10) 0.0373(10) 0.0000(8) 0.0055(9) -0.0017(9)
N1 0.0559(11) 0.0296(9) 0.0338(8) 0.0008(7) 0.0018(7) 0.0010(8)
S1 0.0848(5) 0.0402(3) 0.0393(3) -0.0007(2) -0.0109(3) -0.0044(3)
Cl1A 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5)
C8A 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5)
C8B 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5)
Cl1B 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C2 1.379(3) . ?
C1 C6 1.381(3) . ?
C1 N1 1.428(3) . ?
C2 C3 1.376(3) . ?
C2 C8B 1.488(8) . ?
C2 Cl1A 1.746(1) . ?
C3 C4 1.376(4) . ?
C3 H3 0.95 . ?
C4 C5 1.376(4) . ?
C4 H4 0.95 . ?
C5 C6 1.372(3) . ?
C5 H5 0.95 . ?
C6 C8A 1.451(8) . ?
C6 Cl1B 1.745(1) . ?
C7 N1 1.315(3) . ?
C7 S1 1.647(2) . ?
C7 H7 0.95 . ?
N1 H1 0.84(3) . ?
C8A H8A 0.98 . ?
C8A H8B 0.98 . ?
C8A H8C 0.98 . ?
C8B H8D 0.98 . ?
C8B H8E 0.98 . ?
C8B H8F 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.50(18) . . ?
C2 C1 N1 122.09(18) . . ?
C6 C1 N1 119.40(18) . . ?
C3 C2 C1 120.66(18) . . ?
C3 C2 C8B 120.6(4) . . ?
C1 C2 C8B 118.6(4) . . ?
C3 C2 Cl1A 117.8(2) . . ?
C1 C2 Cl1A 121.56(18) . . ?
C8B C2 Cl1A 3.9(4) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.50(18) . . ?
C5 C6 C8A 122.5(4) . . ?
C1 C6 C8A 115.9(4) . . ?
C5 C6 Cl1B 118.73(19) . . ?
C1 C6 Cl1B 119.76(16) . . ?
C8A C6 Cl1B 4.9(4) . . ?
N1 C7 S1 125.9(2) . . ?
N1 C7 H7 117.1 . . ?
S1 C7 H7 117.1 . . ?
C7 N1 C1 123.9(2) . . ?
C7 N1 H1 122(2) . . ?
C1 N1 H1 114(2) . . ?
C6 C8A H8A 109.5 . . ?
C6 C8A H8B 109.5 . . ?
C6 C8A H8C 109.5 . . ?
C2 C8B H8D 109.5 . . ?
C2 C8B H8E 109.5 . . ?
H8D C8B H8E 109.5 . . ?
C2 C8B H8F 109.5 . . ?
H8D C8B H8F 109.5 . . ?
H8E C8B H8F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.90(18) . . . . ?
N1 C1 C2 C3 -178.65(19) . . . . ?
C6 C1 C2 C8B -174.5(4) . . . . ?
N1 C1 C2 C8B 6.0(4) . . . . ?
C6 C1 C2 Cl1A -177.45(18) . . . . ?
N1 C1 C2 Cl1A 3.0(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C8B C2 C3 C4 174.9(4) . . . . ?
Cl1A C2 C3 C4 178.1(2) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C4 C5 C6 C8A -178.9(5) . . . . ?
C4 C5 C6 Cl1B 177.5(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
N1 C1 C6 C5 179.5(2) . . . . ?
C2 C1 C6 C8A 177.7(4) . . . . ?
N1 C1 C6 C8A -2.8(5) . . . . ?
C2 C1 C6 Cl1B -178.92(15) . . . . ?
N1 C1 C6 Cl1B 0.6(3) . . . . ?
S1 C7 N1 C1 177.65(17) . . . . ?
C2 C1 N1 C7 60.2(3) . . . . ?
C6 C1 N1 C7 -119.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.84(3) 2.60(4) 3.433(2) 176(3) 4_655
C7 H7 S1 0.95 2.92 3.789(2) 153 4_645

###END

_chemical_name_common            2-chloro-6-methylphenylthioamide

