# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_4f
_database_code_depnum_ccdc_archive 'CCDC 1056825'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-(4-fluorophenyl)-4-hydroxythiazolidine-2-thione
_chemical_name_common            
3-(4-fluorophenyl)-4-hydroxythiazolidine-2-thione
_chemical_melting_point          439.15
_chemical_formula_moiety         'C9 H8 F N O S2'
_chemical_formula_sum            'C9 H8 F N O S2'
_chemical_formula_weight         229.28

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.6494(2)
_cell_length_b                   9.5276(4)
_cell_length_c                   32.1006(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2033.66(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8962
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.69

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.502
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13663
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_full        24.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1779
_reflns_number_gt                1661
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+2.9545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1779
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4721(5) 0.5907(4) 0.07338(10) 0.0433(8) Uani 1 1 d . . . . .
H1 H 0.3763 0.6570 0.0856 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5927(7) 0.6618(4) 0.03925(10) 0.0531(9) Uani 1 1 d . . . . .
H2A H 0.5958 0.7625 0.0436 0.064 Uiso 1 1 calc R U . . .
H2B H 0.5331 0.6432 0.0122 0.064 Uiso 1 1 calc R U . . .
C3 C 0.8095(5) 0.5270(3) 0.09199(9) 0.0362(7) Uani 1 1 d . . . . .
C4 C 0.5505(4) 0.4897(3) 0.14395(9) 0.0310(6) Uani 1 1 d . . . . .
C5 C 0.5201(5) 0.5782(3) 0.17719(10) 0.0409(8) Uani 1 1 d . . . . .
H5 H 0.5464 0.6738 0.1748 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4497(6) 0.5225(4) 0.21432(10) 0.0494(9) Uani 1 1 d . . . . .
H6 H 0.4260 0.5802 0.2372 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4156(5) 0.3815(4) 0.21673(10) 0.0473(8) Uani 1 1 d . . . . .
C8 C 0.4442(5) 0.2918(4) 0.18399(11) 0.0464(8) Uani 1 1 d . . . . .
H8 H 0.4183 0.1963 0.1867 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5126(5) 0.3473(3) 0.14684(10) 0.0407(7) Uani 1 1 d . . . . .
H9 H 0.5331 0.2893 0.1239 0.049 Uiso 1 1 calc R U . . .
F1 F 0.3512(4) 0.3271(3) 0.25348(7) 0.0771(8) Uani 1 1 d . . . . .
N1 N 0.6212(4) 0.5461(3) 0.10490(7) 0.0342(6) Uani 1 1 d . . . . .
O1 O 0.3710(4) 0.4741(3) 0.05756(8) 0.0559(7) Uani 1 1 d . . . . .
S1 S 0.99583(13) 0.45457(10) 0.11933(3) 0.0492(3) Uani 1 1 d . . . . .
S2 S 0.84428(17) 0.58978(11) 0.04177(3) 0.0586(4) Uani 1 1 d . . . . .
H1O H 0.272(9) 0.464(5) 0.0737(16) 0.083(17) Uiso 1 1 d . . . . .


_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 O1 1.394(5) . ?
C1 N1 1.479(4) . ?
C1 C2 1.517(5) . ?
C1 H1 0.9800 . ?
C2 S2 1.810(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.331(4) . ?
C3 S1 1.668(3) . ?
C3 S2 1.735(3) . ?
C4 C5 1.375(4) . ?
C4 C9 1.383(4) . ?
C4 N1 1.443(4) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(5) . ?
C6 H6 0.9300 . ?
C7 F1 1.358(4) . ?
C7 C8 1.368(5) . ?
C8 C9 1.382(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O1 H1O 0.84(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
O1 C1 N1 110.1(3) . . ?
O1 C1 C2 110.3(3) . . ?
N1 C1 C2 105.6(3) . . ?
O1 C1 H1 110.2 . . ?
N1 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
C1 C2 S2 106.7(2) . . ?
C1 C2 H2A 110.4 . . ?
S2 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
S2 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
N1 C3 S1 126.3(2) . . ?
N1 C3 S2 111.6(2) . . ?
S1 C3 S2 122.18(19) . . ?
C5 C4 C9 121.6(3) . . ?
C5 C4 N1 119.6(3) . . ?
C9 C4 N1 118.9(3) . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
F1 C7 C6 118.5(3) . . ?
F1 C7 C8 118.2(3) . . ?
C6 C7 C8 123.3(3) . . ?
C7 C8 C9 118.0(3) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C8 C9 C4 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C3 N1 C4 121.7(3) . . ?
C3 N1 C1 117.2(2) . . ?
C4 N1 C1 118.9(3) . . ?
C1 O1 H1O 104(3) . . ?
C3 S2 C2 92.81(15) . . ?

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
O1 C1 C2 S2 -93.9(3) . . . . ?
N1 C1 C2 S2 25.1(3) . . . . ?
C9 C4 C5 C6 -0.1(5) . . . . ?
N1 C4 C5 C6 179.2(3) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C6 C7 F1 178.4(3) . . . . ?
C5 C6 C7 C8 -1.2(6) . . . . ?
F1 C7 C8 C9 -179.0(3) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C4 0.3(5) . . . . ?
C5 C4 C9 C8 -0.5(5) . . . . ?
N1 C4 C9 C8 -179.8(3) . . . . ?
S1 C3 N1 C4 -7.3(4) . . . . ?
S2 C3 N1 C4 173.6(2) . . . . ?
S1 C3 N1 C1 -170.2(2) . . . . ?
S2 C3 N1 C1 10.6(3) . . . . ?
C5 C4 N1 C3 106.0(3) . . . . ?
C9 C4 N1 C3 -74.7(4) . . . . ?
C5 C4 N1 C1 -91.4(3) . . . . ?
C9 C4 N1 C1 87.9(3) . . . . ?
O1 C1 N1 C3 95.1(3) . . . . ?
C2 C1 N1 C3 -24.0(4) . . . . ?
O1 C1 N1 C4 -68.3(3) . . . . ?
C2 C1 N1 C4 172.6(2) . . . . ?
N1 C3 S2 C2 5.1(2) . . . . ?
S1 C3 S2 C2 -174.1(2) . . . . ?
C1 C2 S2 C3 -18.1(2) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_chemical_compound_source        Synthesised
