# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
# 
#######################################################################

data_flcb171121
_database_code_depnum_ccdc_archive 'CCDC 1855018'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 F2 O S'
_chemical_formula_sum            'C8 H8 F2 O S'
_chemical_formula_weight         190.20

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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.91110(10)
_cell_length_b                   8.9793(2)
_cell_length_c                   18.9180(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     834.25(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13041
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.367
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19783
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_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             1924
_reflns_number_gt                1817
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0577P)²+0.0931P] where P=(Fo²+2Fc²)/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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.058(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1924
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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 0.2954(4) 0.0081(3) 0.08995(11) 0.0251(5) Uani 1 1 d . . . . .
C2 C 0.3647(5) -0.1249(3) 0.12227(13) 0.0301(6) Uani 1 1 d . . . . .
H2 H 0.2853 -0.2159 0.1071 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5516(7) -0.1233(3) 0.17713(12) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.5992 -0.2143 0.1996 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6711(5) 0.0084(3) 0.20009(12) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.6002(6) 0.1403(3) 0.16599(13) 0.0339(6) Uani 1 1 d . . . . .
H5 H 0.6829 0.2311 0.1802 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4106(6) 0.1412(3) 0.11153(13) 0.0312(5) Uani 1 1 d . . . . .
H6 H 0.3606 0.2321 0.0894 0.037 Uiso 1 1 calc R U . . .
C7 C 0.8731(6) 0.0087(4) 0.26001(14) 0.0426(7) Uani 1 1 d . . . . .
H7A H 0.8576 -0.0846 0.2866 0.064 Uiso 1 1 calc R U . . .
H7B H 0.8352 0.0929 0.2915 0.064 Uiso 1 1 calc R U . . .
H7C H 1.0579 0.0180 0.2410 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3052(5) -0.0265(3) -0.05085(12) 0.0284(5) Uani 1 1 d . . . . .
H8 H 0.4080 -0.1206 -0.0415 0.034 Uiso 1 1 calc R U . . .
O1 O -0.1121(3) -0.12677(19) 0.02154(9) 0.0323(4) Uani 1 1 d . . . . .
F1 F 0.1626(3) -0.03476(19) -0.11216(7) 0.0418(4) Uani 1 1 d . . . . .
F2 F 0.4747(3) 0.09138(18) -0.05695(8) 0.0398(4) Uani 1 1 d . . . . .
S1 S 0.05396(11) 0.01155(6) 0.01944(3) 0.0257(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0233(11) 0.0287(11) 0.0233(10) -0.0001(9) 0.0019(8) 0.0011(11)
C2 0.0330(14) 0.0265(12) 0.0307(12) 0.0014(10) 0.0006(10) -0.0005(10)
C3 0.0378(14) 0.0334(12) 0.0280(11) 0.0046(9) 0.0021(11) 0.0066(12)
C4 0.0264(11) 0.0434(14) 0.0236(11) -0.0032(11) 0.0027(9) 0.0049(12)
C5 0.0367(15) 0.0335(13) 0.0316(12) -0.0040(10) -0.0035(11) -0.0041(12)
C6 0.0364(14) 0.0267(11) 0.0306(11) 0.0015(10) -0.0027(11) 0.0011(11)
C7 0.0376(14) 0.0607(19) 0.0296(12) -0.0036(13) -0.0059(11) 0.0064(15)
C8 0.0274(11) 0.0296(12) 0.0282(11) 0.0035(10) -0.0008(10) -0.0035(10)
O1 0.0257(9) 0.0328(9) 0.0383(9) -0.0005(8) 0.0012(8) -0.0069(7)
F1 0.0465(9) 0.0529(10) 0.0259(7) -0.0015(7) -0.0028(7) -0.0075(8)
F2 0.0378(9) 0.0418(8) 0.0398(8) 0.0067(7) 0.0027(7) -0.0135(8)
S1 0.0224(3) 0.0266(3) 0.0282(3) 0.0004(2) -0.0012(2) 0.0010(2)

_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 1.383(3) . ?
C1 C2 1.384(3) . ?
C1 S1 1.785(2) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 C7 1.506(3) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 F2 1.352(3) . ?
C8 F1 1.357(3) . ?
C8 S1 1.846(2) . ?
C8 H8 1.0000 . ?
O1 S1 1.4863(17) . ?

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 120.9(2) . . ?
C6 C1 S1 118.52(18) . . ?
C2 C1 S1 120.55(18) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C7 121.0(2) . . ?
C5 C4 C7 120.8(3) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
F2 C8 F1 106.71(18) . . ?
F2 C8 S1 109.15(17) . . ?
F1 C8 S1 106.31(16) . . ?
F2 C8 H8 111.5 . . ?
F1 C8 H8 111.5 . . ?
S1 C8 H8 111.5 . . ?
O1 S1 C1 109.27(11) . . ?
O1 S1 C8 103.37(10) . . ?
C1 S1 C8 95.23(10) . . ?

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 0.3(4) . . . . ?
S1 C1 C2 C3 -179.6(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 C7 179.7(2) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C7 C4 C5 C6 -178.9(2) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
S1 C1 C6 C5 -179.5(2) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C6 C1 S1 O1 -160.22(19) . . . . ?
C2 C1 S1 O1 19.7(2) . . . . ?
C6 C1 S1 C8 93.6(2) . . . . ?
C2 C1 S1 C8 -86.5(2) . . . . ?
F2 C8 S1 O1 -178.64(15) . . . . ?
F1 C8 S1 O1 66.61(18) . . . . ?
F2 C8 S1 C1 -67.39(17) . . . . ?
F1 C8 S1 C1 177.86(18) . . . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.124

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL import in P 21 21 21
CELL  0.71073   4.9111   8.9793  18.9180   90.000   90.000   90.000
ZERR     4.00   0.0001   0.0002   0.0004    0.000    0.000    0.000
LATT  -1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y, - Z
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    F    S
UNIT  32 32 4 8 4
MERG   2
FMAP   2
PLAN   10
SIZE     0.120   0.180   0.340
ACTA
BOND   $H
CONF
L.S.   8
TEMP  -100.00
WGHT    0.057700    0.093100
EXTI    0.057579
FVAR       0.69901
C1    1    0.295372    0.008146    0.089953    11.00000    0.02327    0.02867 =
         0.02328   -0.00010    0.00188    0.00114
C2    1    0.364718   -0.124876    0.122269    11.00000    0.03296    0.02655 =
         0.03068    0.00139    0.00059   -0.00052
AFIX  43
H2    2    0.285345   -0.215883    0.107060    11.00000   -1.20000
AFIX   0
C3    1    0.551630   -0.123293    0.177127    11.00000    0.03781    0.03338 =
         0.02803    0.00464    0.00209    0.00659
AFIX  43
H3    2    0.599172   -0.214310    0.199557    11.00000   -1.20000
AFIX   0
C4    1    0.671135    0.008377    0.200089    11.00000    0.02644    0.04335 =
         0.02359   -0.00319    0.00269    0.00491
C5    1    0.600205    0.140266    0.165992    11.00000    0.03667    0.03348 =
         0.03162   -0.00402   -0.00355   -0.00414
AFIX  43
H5    2    0.682887    0.231092    0.180224    11.00000   -1.20000
AFIX   0
C6    1    0.410616    0.141181    0.111535    11.00000    0.03645    0.02673 =
         0.03057    0.00145   -0.00267    0.00107
AFIX  43
H6    2    0.360639    0.232087    0.089361    11.00000   -1.20000
AFIX   0
C7    1    0.873127    0.008668    0.260015    11.00000    0.03760    0.06067 =
         0.02963   -0.00359   -0.00594    0.00640
AFIX 137
H7A   2    0.857624   -0.084640    0.286583    11.00000   -1.50000
H7B   2    0.835239    0.092865    0.291474    11.00000   -1.50000
H7C   2    1.057922    0.017969    0.240972    11.00000   -1.50000
AFIX   0
C8    1    0.305202   -0.026537   -0.050851    11.00000    0.02738    0.02965 =
         0.02824    0.00348   -0.00076   -0.00349
AFIX  13
H8    2    0.407964   -0.120630   -0.041476    11.00000   -1.20000
AFIX   0
O1    3   -0.112090   -0.126765    0.021542    11.00000    0.02567    0.03283 =
         0.03830   -0.00046    0.00124   -0.00690
F1    4    0.162604   -0.034759   -0.112157    11.00000    0.04649    0.05294 =
         0.02588   -0.00149   -0.00277   -0.00748
F2    4    0.474711    0.091381   -0.056949    11.00000    0.03779    0.04180 =
         0.03979    0.00672    0.00270   -0.01349
S1    5    0.053961    0.011553    0.019439    11.00000    0.02244    0.02664 =
         0.02816    0.00038   -0.00121    0.00097
HKLF    4

REM  import in P 21 21 21
REM R1 =  0.0327 for    1817 Fo > 4sig(Fo)  and  0.0388 for all    1924 data
REM    111 parameters refined using      0 restraints

END

WGHT      0.0577      0.0931

REM Highest difference peak  0.422,  deepest hole -0.414,  1-sigma level  0.124
Q1    1   0.9586 -0.0683  0.2596  11.00000  0.05    0.42
Q2    1   1.0008  0.1279  0.2593  11.00000  0.05    0.38
Q3    1   1.0034 -0.2126  0.2430  11.00000  0.05    0.33
Q4    1   1.0197  0.2238  0.2420  11.00000  0.05    0.33
Q5    1   0.8453 -0.2574  0.2406  11.00000  0.05    0.26
Q6    1   1.1831  0.1455  0.2747  11.00000  0.05    0.25
Q7    1   0.8505  0.2894  0.2366  11.00000  0.05    0.22
Q8    1   0.1650  0.0071  0.0623  11.00000  0.05    0.20
Q9    1   0.7158 -0.2381  0.3208  11.00000  0.05    0.18
Q10   1   1.2351  0.0078  0.2631  11.00000  0.05    0.18
;
_shelx_res_checksum              52670
