# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_General
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_audit_creation_date             2010-09-28
_audit_creation_method           'by CrystalStructure 4.0.1'
_audit_update_record             ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_coeditor_code           ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name        'Masahito Ochiai'
_publ_contact_author_email       mochiai@ph.tokushima-u.ac.jp
_publ_contact_author_fax         'ENTER FAX NUMBER'
_publ_contact_author_phone       'ENTER PHONE NUMBER'
_publ_contact_letter             
;
ENTER TEXT OF LETTER
;
_publ_requested_category         'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name    ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title              
;
ENTER SECTION TITLE
;
_publ_section_title_footnote     
;
ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Masahito Ochiai'
;
FIRST AUTHORS FOOTNOTES
;
;
FIRST AUTHORS ADDRESS
;
'Shinichi Yamane' '' ''
'Md. Mahbubul Hoque' '' ''
'Kazunori Miyamoto' '' ''
_publ_section_synopsis           
;
ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract           
;
ENTER ABSTRACT
;
_publ_section_comment            
;
ENTER TEXT
;
_publ_section_references         
;
ENTER OTHER REFERENCES

Johnson, C.K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory,
Tennessee, USA.

Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing
Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo
196-8666, Japan

Rigaku & RAC (2007). CrystalStructure (Version 3.80). Single Crystal
Structure Analysis Software. Rigaku, Tokyo 196-8666, Japan. Rigaku
Americas, TX, USA 77381-5209.

Sheldrick, G.M. (1997). SHELXS97. Program for the Solution of Crystal
Structures. University of Gottingen, Germany.

Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany.

;
_publ_section_figure_captions    
;
ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep         
;
ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement   
;
ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_SYA-174-1
_database_code_depnum_ccdc_archive 'CCDC 865366'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C5 H8 F3 N O3 S'
_chemical_formula_moiety         'C5 H8 F3 N O3 S'
_chemical_formula_weight         219.18
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 43'
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_Int_Tables_number      78
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z+3/4'
'-x, -y, z+1/2'
'y, -x, z+1/4'
#------------------------------------------------------------------------------
_cell_length_a                   8.0230(9)
_cell_length_b                   8.0230(9)
_cell_length_c                   13.8300(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     890.21(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6074
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      27.37
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448.00
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.962

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K$B%((Ba'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       $B%((Bw
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8777
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_full        27.37
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_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       -16
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
Refinement was performed using all reflections. The weighted
R-factor (wR) and goodness of fit (S) are based on F^2^.
R-factor (gt) are based on F. The threshold expression of
F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt).
;
_reflns_number_total             1996
_reflns_number_gt                1362
_reflns_threshold_expression     F^2^>2.0$B%((Bs(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0705
_refine_ls_number_restraints     135
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1996
_refine_ls_number_parameters     129
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[$B%((Bs^2^(Fo^2^)+(0.0263P)^2^+0.0443P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 938 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.12(12)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.22724(13) 0.22579(13) 0.33944(8) 0.0510(2) Uani 1 1 d U . .
F1 F -0.1663(3) 0.4067(4) 0.49125(18) 0.0934(8) Uani 1 1 d U . .
F2 F -0.2011(3) 0.5471(3) 0.36176(17) 0.0796(8) Uani 1 1 d U . .
F3 F -0.4097(3) 0.4387(4) 0.4320(2) 0.0956(9) Uani 1 1 d U . .
O1 O 0.0144(3) 0.1717(3) 0.14537(18) 0.0618(7) Uani 1 1 d U . .
O2 O -0.2596(4) 0.0949(3) 0.40528(19) 0.0704(8) Uani 1 1 d U . .
O3 O -0.3279(3) 0.2515(4) 0.25640(17) 0.0681(8) Uani 1 1 d U . .
N1 N -0.0372(4) 0.2282(4) 0.31086(18) 0.0511(8) Uani 1 1 d U . .
H1N H 0.0350 0.1876 0.3515 0.061 Uiso 1 1 calc R . .
C1 C 0.0233(4) 0.2956(4) 0.2194(2) 0.0459(8) Uani 1 1 d U . .
H1 H -0.0438 0.3940 0.2007 0.055 Uiso 1 1 calc R . .
C2 C 0.1777(5) 0.1047(6) 0.1299(4) 0.0746(12) Uani 1 1 d DU . .
H2A H 0.1902 0.0639 0.0635 0.089 Uiso 0.68 1 calc PR A 1
H2B H 0.2007 0.0132 0.1749 0.089 Uiso 0.68 1 calc PR A 1
H2C H 0.2104 0.1199 0.0622 0.089 Uiso 0.32 1 calc PR A 2
H2D H 0.1782 -0.0149 0.1442 0.089 Uiso 0.32 1 calc PR A 2
C3 C 0.2887(7) 0.2465(8) 0.1481(5) 0.0731(16) Uani 0.68 1 d PDU A 1
H3A H 0.3017 0.3143 0.0896 0.088 Uiso 0.68 1 calc PR A 1
H3B H 0.3989 0.2080 0.1690 0.088 Uiso 0.68 1 calc PR A 1
C3A C 0.2949(13) 0.1908(14) 0.1929(10) 0.070(3) Uani 0.32 1 d PDU A 2
H3C H 0.3970 0.2194 0.1577 0.084 Uiso 0.32 1 calc PR A 2
H3D H 0.3244 0.1207 0.2484 0.084 Uiso 0.32 1 calc PR A 2
C4 C 0.2074(5) 0.3432(6) 0.2252(3) 0.0684(10) Uani 1 1 d DU . .
H4A H 0.2222 0.4631 0.2146 0.082 Uiso 0.68 1 calc PR A 1
H4B H 0.2537 0.3141 0.2886 0.082 Uiso 0.68 1 calc PR A 1
H4C H 0.2325 0.4375 0.1826 0.082 Uiso 0.32 1 calc PR A 2
H4D H 0.2389 0.3725 0.2916 0.082 Uiso 0.32 1 calc PR A 2
C5 C -0.2516(6) 0.4140(6) 0.4090(3) 0.0632(10) Uani 1 1 d U . .

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 0.0464(6) 0.0514(6) 0.0552(4) 0.0059(5) -0.0006(5) -0.0010(3)
F1 0.102(2) 0.116(2) 0.0615(13) -0.0232(15) -0.0003(14) 0.0054(17)
F2 0.0873(18) 0.0569(13) 0.0946(16) -0.0022(12) 0.0107(14) -0.0065(12)
F3 0.0656(17) 0.098(2) 0.123(2) -0.0048(17) 0.0318(15) 0.0227(14)
O1 0.0417(14) 0.0799(18) 0.0637(14) -0.0298(13) 0.0015(13) -0.0011(12)
O2 0.076(2) 0.0579(16) 0.0778(17) 0.0274(14) 0.0128(18) -0.0086(15)
O3 0.0554(15) 0.081(2) 0.0674(16) 0.0068(15) -0.0191(13) -0.0051(16)
N1 0.0457(15) 0.0636(19) 0.0441(14) 0.0089(15) 0.0003(12) 0.0070(14)
C1 0.0514(18) 0.046(2) 0.0408(16) -0.0052(16) -0.0030(15) -0.0016(17)
C2 0.045(2) 0.093(3) 0.086(3) -0.024(2) 0.0055(19) 0.009(2)
C3 0.048(3) 0.103(4) 0.068(3) -0.002(3) -0.001(3) -0.007(3)
C3A 0.044(4) 0.099(6) 0.067(5) -0.003(5) 0.004(5) -0.008(4)
C4 0.062(2) 0.079(2) 0.065(2) -0.0099(19) 0.004(2) -0.0229(19)
C5 0.054(2) 0.073(2) 0.063(2) 0.001(2) 0.009(2) 0.001(2)

#==============================================================================
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;
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 O2 1.414(3) . ?
S1 O3 1.419(3) . ?
S1 N1 1.575(3) . ?
S1 C5 1.802(4) . ?
F1 C5 1.328(5) . ?
F2 C5 1.316(5) . ?
F3 C5 1.322(5) . ?
O1 C1 1.429(4) . ?
O1 C2 1.433(4) . ?
N1 C1 1.459(4) . ?
C1 C4 1.528(5) . ?
C2 C3A 1.456(8) . ?
C2 C3 1.467(6) . ?
C3 C4 1.471(6) . ?
C3A C4 1.479(8) . ?

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
O2 S1 O3 121.62(19) . . ?
O2 S1 N1 110.40(17) . . ?
O3 S1 N1 110.25(16) . . ?
O2 S1 C5 105.00(19) . . ?
O3 S1 C5 104.40(19) . . ?
N1 S1 C5 103.22(19) . . ?
C1 O1 C2 108.8(3) . . ?
C1 N1 S1 123.0(2) . . ?
O1 C1 N1 110.3(3) . . ?
O1 C1 C4 105.1(3) . . ?
N1 C1 C4 111.6(3) . . ?
O1 C2 C3A 108.9(4) . . ?
O1 C2 C3 103.8(4) . . ?
C2 C3 C4 105.3(4) . . ?
C2 C3A C4 105.5(6) . . ?
C3 C4 C1 105.0(3) . . ?
C3A C4 C1 103.6(5) . . ?
F2 C5 F3 107.1(4) . . ?
F2 C5 F1 107.6(4) . . ?
F3 C5 F1 107.2(4) . . ?
F2 C5 S1 112.4(3) . . ?
F3 C5 S1 111.0(3) . . ?
F1 C5 S1 111.4(3) . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 . . 4_555 2.822(4) 0.870 2.049 147.6 no

#===END========================================================================