# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_gil7589
_database_code_depnum_ccdc_archive 'CCDC 1048074'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 F S'
_chemical_formula_weight         272.37
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   7.9685(7)
_cell_length_b                   11.0136(9)
_cell_length_c                   16.1416(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1416.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2088
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    1.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5443
_exptl_absorpt_correction_T_max  0.7692
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7627
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.48
_diffrn_reflns_theta_max         67.00
_reflns_number_total             2377
_reflns_number_gt                2361
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0286P)²+0.3585P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(17)
_refine_ls_number_reflns         2377
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.93781(7) 0.41087(4) 0.31290(3) 0.05339(16) Uani 1 1 d . . .
F1 F 0.64757(13) 0.58400(9) 0.27409(5) 0.0444(2) Uani 1 1 d . . .
C1 C 1.0956(3) 0.46236(17) 0.24024(13) 0.0526(5) Uani 1 1 d . . .
H1A H 1.1906 0.4059 0.2391 0.063 Uiso 1 1 calc R . .
H1B H 1.0484 0.4682 0.1843 0.063 Uiso 1 1 calc R . .
C2 C 1.1516(2) 0.58616(18) 0.27042(12) 0.0507(5) Uani 1 1 d . . .
H2A H 1.2050 0.6316 0.2253 0.061 Uiso 1 1 calc R . .
H2B H 1.2323 0.5777 0.3159 0.061 Uiso 1 1 calc R . .
C3 C 0.9953(2) 0.65161(15) 0.30003(12) 0.0448(4) Uani 1 1 d . . .
H3A H 0.9278 0.6778 0.2525 0.054 Uiso 1 1 calc R . .
H3B H 1.0265 0.7236 0.3323 0.054 Uiso 1 1 calc R . .
C4 C 0.8948(2) 0.56339(14) 0.35391(10) 0.0374(4) Uani 1 1 d . . .
H4 H 0.9390 0.5677 0.4112 0.045 Uiso 1 1 calc R . .
C5 C 0.7059(2) 0.58891(16) 0.35662(9) 0.0338(3) Uani 1 1 d . . .
C11 C 0.6667(2) 0.71714(15) 0.38732(10) 0.0327(3) Uani 1 1 d . . .
C12 C 0.7583(2) 0.77195(16) 0.45032(10) 0.0397(4) Uani 1 1 d . . .
H12 H 0.8454 0.7288 0.4764 0.048 Uiso 1 1 calc R . .
C13 C 0.7226(2) 0.88962(16) 0.47516(11) 0.0454(4) Uani 1 1 d . . .
H13 H 0.7854 0.9256 0.5179 0.055 Uiso 1 1 calc R . .
C14 C 0.5955(3) 0.95408(16) 0.43744(12) 0.0500(5) Uani 1 1 d . . .
H14 H 0.5727 1.0344 0.4536 0.060 Uiso 1 1 calc R . .
C15 C 0.5023(2) 0.90017(17) 0.37608(11) 0.0476(4) Uani 1 1 d . . .
H15 H 0.4147 0.9437 0.3508 0.057 Uiso 1 1 calc R . .
C16 C 0.5361(2) 0.78223(16) 0.35098(10) 0.0386(4) Uani 1 1 d . . .
H16 H 0.4706 0.7461 0.3093 0.046 Uiso 1 1 calc R . .
C21 C 0.6132(2) 0.49102(14) 0.40515(10) 0.0349(4) Uani 1 1 d . . .
C22 C 0.6398(2) 0.47796(16) 0.48979(11) 0.0435(4) Uani 1 1 d . . .
H22 H 0.7120 0.5316 0.5177 0.052 Uiso 1 1 calc R . .
C23 C 0.5595(3) 0.38571(18) 0.53311(12) 0.0526(5) Uani 1 1 d . . .
H23 H 0.5792 0.3767 0.5902 0.063 Uiso 1 1 calc R . .
C24 C 0.4517(3) 0.30760(18) 0.49351(15) 0.0598(5) Uani 1 1 d . . .
H24 H 0.3971 0.2458 0.5233 0.072 Uiso 1 1 calc R . .
C25 C 0.4247(3) 0.32056(19) 0.41053(14) 0.0629(6) Uani 1 1 d . . .
H25 H 0.3506 0.2676 0.3832 0.076 Uiso 1 1 calc R . .
C26 C 0.5056(2) 0.41116(17) 0.36617(12) 0.0487(4) Uani 1 1 d . . .
H26 H 0.4869 0.4183 0.3089 0.058 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.8107(19) . ?
S1 C4 1.8379(16) . ?
F1 C5 1.4120(17) . ?
C1 C2 1.515(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.516(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.530(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.532(2) . ?
C4 H4 0.9900 . ?
C5 C21 1.523(2) . ?
C5 C11 1.529(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C26 1.380(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.364(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 94.39(8) . . ?
C2 C1 S1 106.14(12) . . ?
C2 C1 H1A 110.5 . . ?
S1 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
S1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C1 C2 C3 106.72(15) . . ?
C1 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 107.90(14) . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C3 C4 C5 114.47(14) . . ?
C3 C4 S1 106.13(11) . . ?
C5 C4 S1 111.17(12) . . ?
C3 C4 H4 108.3 . . ?
C5 C4 H4 108.3 . . ?
S1 C4 H4 108.3 . . ?
F1 C5 C21 107.38(12) . . ?
F1 C5 C11 105.90(13) . . ?
C21 C5 C11 112.84(12) . . ?
F1 C5 C4 106.82(12) . . ?
C21 C5 C4 111.16(13) . . ?
C11 C5 C4 112.29(13) . . ?
C12 C11 C16 118.49(15) . . ?
C12 C11 C5 122.08(15) . . ?
C16 C11 C5 119.43(15) . . ?
C13 C12 C11 120.65(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.31(18) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.54(17) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.73(17) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.26(17) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C26 C21 C22 118.46(16) . . ?
C26 C21 C5 121.18(15) . . ?
C22 C21 C5 120.33(15) . . ?
C23 C22 C21 120.03(18) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.78(18) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.35(19) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.79(18) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?

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
C4 S1 C1 C2 19.13(15) . . . . ?
S1 C1 C2 C3 -39.91(19) . . . . ?
C1 C2 C3 C4 46.2(2) . . . . ?
C2 C3 C4 C5 -153.62(15) . . . . ?
C2 C3 C4 S1 -30.61(18) . . . . ?
C1 S1 C4 C3 6.42(14) . . . . ?
C1 S1 C4 C5 131.48(13) . . . . ?
C3 C4 C5 F1 58.17(18) . . . . ?
S1 C4 C5 F1 -62.07(15) . . . . ?
C3 C4 C5 C21 175.01(14) . . . . ?
S1 C4 C5 C21 54.77(15) . . . . ?
C3 C4 C5 C11 -57.50(18) . . . . ?
S1 C4 C5 C11 -177.75(10) . . . . ?
F1 C5 C11 C12 -154.32(14) . . . . ?
C21 C5 C11 C12 88.49(19) . . . . ?
C4 C5 C11 C12 -38.1(2) . . . . ?
F1 C5 C11 C16 25.19(19) . . . . ?
C21 C5 C11 C16 -92.00(17) . . . . ?
C4 C5 C11 C16 141.42(15) . . . . ?
C16 C11 C12 C13 -1.3(2) . . . . ?
C5 C11 C12 C13 178.19(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C12 C11 C16 C15 1.7(2) . . . . ?
C5 C11 C16 C15 -177.83(15) . . . . ?
F1 C5 C21 C26 4.9(2) . . . . ?
C11 C5 C21 C26 121.20(17) . . . . ?
C4 C5 C21 C26 -111.62(18) . . . . ?
F1 C5 C21 C22 -177.12(15) . . . . ?
C11 C5 C21 C22 -60.8(2) . . . . ?
C4 C5 C21 C22 66.38(19) . . . . ?
C26 C21 C22 C23 0.4(3) . . . . ?
C5 C21 C22 C23 -177.68(16) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C5 C21 C26 C25 178.52(18) . . . . ?
C24 C25 C26 C21 -0.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_gil7668
_database_code_depnum_ccdc_archive 'CCDC 1048075'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 F O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         288.36
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.4841(3)
_cell_length_b                   9.9993(3)
_cell_length_c                   14.7157(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1395.55(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1324
_cell_measurement_theta_min      22.7152
_cell_measurement_theta_max      75.5807
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.148
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608

_exptl_absorpt_coefficient_mu    2.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            6088
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_theta_min         5.35
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_full        68.28
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2488
_reflns_number_gt                2423
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0670
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_number_reflns         2488
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.2287P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 978 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.0164(3) 0.6856(2) 0.47135(15) 0.0196(5) Uani d . . . 1 . .
H H1A -0.0948 0.7174 0.4326 0.024 Uiso calc U . R 1 . .
H H1B 0.0572 0.7557 0.4736 0.024 Uiso calc U . R 1 . .
F F1 0.21437(14) 0.67881(12) 0.66370(8) 0.0155(3) Uani d . . . 1 . .
O O1 -0.21328(17) 0.56956(17) 0.57347(11) 0.0230(4) Uani d . . . 1 . .
S S1 -0.07936(6) 0.64738(5) 0.58480(3) 0.01533(15) Uani d . . . 1 . .
C C2 0.0439(3) 0.5561(2) 0.43437(15) 0.0203(5) Uani d . . . 1 . .
H H2A 0.0973 0.5723 0.3776 0.024 Uiso calc U . R 1 . .
H H2B -0.0321 0.4907 0.4219 0.024 Uiso calc U . R 1 . .
C C3 0.1412(3) 0.5057(3) 0.50943(15) 0.0187(5) Uani d . . . 1 . .
H H3A 0.229 0.5591 0.5109 0.022 Uiso calc U . R 1 . .
H H3B 0.1662 0.4109 0.4988 0.022 Uiso calc U . R 1 . .
C C4 0.0611(2) 0.5204(2) 0.59940(14) 0.0140(4) Uani d . . . 1 . .
H H4 0.0135 0.433 0.6116 0.017 Uiso calc U . R 1 . .
C C5 0.1535(2) 0.5521(2) 0.68214(14) 0.0124(5) Uani d . . . 1 . .
C C11 0.2734(2) 0.4511(2) 0.69045(13) 0.0125(5) Uani d . . . 1 . .
C C12 0.2443(3) 0.3212(2) 0.71990(14) 0.0165(5) Uani d . . . 1 . .
H H12 0.1505 0.297 0.7355 0.02 Uiso calc U . R 1 . .
C C13 0.3512(3) 0.2275(2) 0.72653(16) 0.0179(5) Uani d . . . 1 . .
H H13 0.3304 0.1391 0.7462 0.021 Uiso calc U . R 1 . .
C C14 0.4887(3) 0.2621(2) 0.70457(15) 0.0176(5) Uani d . . . 1 . .
H H14 0.562 0.1978 0.7093 0.021 Uiso calc U . R 1 . .
C C15 0.5186(2) 0.3909(2) 0.67570(14) 0.0152(5) Uani d . . . 1 . .
H H15 0.6128 0.4152 0.6612 0.018 Uiso calc U . R 1 . .
C C16 0.4111(2) 0.4848(2) 0.66797(13) 0.0139(4) Uani d . . . 1 . .
H H16 0.432 0.5726 0.6472 0.017 Uiso calc U . R 1 . .
C C21 0.0714(2) 0.5659(2) 0.77099(14) 0.0125(4) Uani d . . . 1 . .
C C22 0.1188(2) 0.6550(2) 0.83749(14) 0.0157(5) Uani d . . . 1 . .
H H22 0.1985 0.7099 0.8258 0.019 Uiso calc U . R 1 . .
C C23 0.0498(2) 0.6636(2) 0.92069(15) 0.0198(5) Uani d . . . 1 . .
H H23 0.0831 0.724 0.9657 0.024 Uiso calc U . R 1 . .
C C24 -0.0668(3) 0.5849(2) 0.93843(15) 0.0211(5) Uani d . . . 1 . .
H H24 -0.1144 0.5922 0.995 0.025 Uiso calc U . R 1 . .
C C25 -0.1141(2) 0.4953(2) 0.87329(15) 0.0194(5) Uani d . . . 1 . .
H H25 -0.1935 0.4403 0.8856 0.023 Uiso calc U . R 1 . .
C C26 -0.0454(2) 0.4859(2) 0.78967(15) 0.0168(5) Uani d . . . 1 . .
H H26 -0.0784 0.4246 0.7452 0.02 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.516(3) ?
C1 S1 . 1.814(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
F1 C5 . 1.419(2) ?
O1 S1 . 1.4989(17) ?
S1 C4 . 1.853(2) ?
C2 C3 . 1.525(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.533(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.533(3) ?
C4 H4 . 1.0 ?
C5 C11 . 1.526(3) ?
C5 C21 . 1.528(3) ?
C11 C16 . 1.388(3) ?
C11 C12 . 1.398(3) ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.391(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.394(3) ?
C21 C22 . 1.398(3) ?
C22 C23 . 1.391(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.382(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.386(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.396(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 S1 . . 105.95(15) ?
C2 C1 H1A . . 110.5 ?
S1 C1 H1A . . 110.5 ?
C2 C1 H1B . . 110.5 ?
S1 C1 H1B . . 110.5 ?
H1A C1 H1B . . 108.7 ?
O1 S1 C1 . . 106.61(11) ?
O1 S1 C4 . . 105.45(10) ?
C1 S1 C4 . . 90.83(10) ?
C1 C2 C3 . . 104.49(18) ?
C1 C2 H2A . . 110.9 ?
C3 C2 H2A . . 110.9 ?
C1 C2 H2B . . 110.9 ?
C3 C2 H2B . . 110.9 ?
H2A C2 H2B . . 108.9 ?
C2 C3 C4 . . 107.13(18) ?
C2 C3 H3A . . 110.3 ?
C4 C3 H3A . . 110.3 ?
C2 C3 H3B . . 110.3 ?
C4 C3 H3B . . 110.3 ?
H3A C3 H3B . . 108.5 ?
C5 C4 C3 . . 115.01(18) ?
C5 C4 S1 . . 111.17(15) ?
C3 C4 S1 . . 108.74(14) ?
C5 C4 H4 . . 107.2 ?
C3 C4 H4 . . 107.2 ?
S1 C4 H4 . . 107.2 ?
F1 C5 C11 . . 107.60(18) ?
F1 C5 C21 . . 106.87(16) ?
C11 C5 C21 . . 111.78(16) ?
F1 C5 C4 . . 105.39(16) ?
C11 C5 C4 . . 110.67(17) ?
C21 C5 C4 . . 114.05(18) ?
C16 C11 C12 . . 119.1(2) ?
C16 C11 C5 . . 121.44(19) ?
C12 C11 C5 . . 119.5(2) ?
C13 C12 C11 . . 120.4(2) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 120.2(2) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C15 C14 C13 . . 119.7(2) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C16 . . 120.2(2) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C11 C16 C15 . . 120.4(2) ?
C11 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C26 C21 C22 . . 118.9(2) ?
C26 C21 C5 . . 121.46(19) ?
C22 C21 C5 . . 119.54(19) ?
C23 C22 C21 . . 120.3(2) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C24 C23 C22 . . 120.5(2) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C23 C24 C25 . . 119.7(2) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
C24 C25 C26 . . 120.1(2) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C21 C26 C25 . . 120.4(2) ?
C21 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 S1 O1 . . . . -74.77(18) ?
C2 C1 S1 C4 . . . . 31.63(17) ?
S1 C1 C2 C3 . . . . -49.4(2) ?
C1 C2 C3 C4 . . . . 45.2(2) ?
C2 C3 C4 C5 . . . . -147.24(19) ?
C2 C3 C4 S1 . . . . -21.9(2) ?
O1 S1 C4 C5 . . . . -130.49(14) ?
C1 S1 C4 C5 . . . . 122.02(16) ?
O1 S1 C4 C3 . . . . 101.91(16) ?
C1 S1 C4 C3 . . . . -5.58(17) ?
C3 C4 C5 F1 . . . . 63.2(2) ?
S1 C4 C5 F1 . . . . -60.89(18) ?
C3 C4 C5 C11 . . . . -52.8(2) ?
S1 C4 C5 C11 . . . . -176.93(14) ?
C3 C4 C5 C21 . . . . -179.88(18) ?
S1 C4 C5 C21 . . . . 56.0(2) ?
F1 C5 C11 C16 . . . . -9.1(2) ?
C21 C5 C11 C16 . . . . -126.2(2) ?
C4 C5 C11 C16 . . . . 105.5(2) ?
F1 C5 C11 C12 . . . . 171.95(17) ?
C21 C5 C11 C12 . . . . 54.9(3) ?
C4 C5 C11 C12 . . . . -73.4(2) ?
C16 C11 C12 C13 . . . . 0.0(3) ?
C5 C11 C12 C13 . . . . 178.97(19) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C12 C13 C14 C15 . . . . -0.2(3) ?
C13 C14 C15 C16 . . . . -0.6(3) ?
C12 C11 C16 C15 . . . . -0.8(3) ?
C5 C11 C16 C15 . . . . -179.70(18) ?
C14 C15 C16 C11 . . . . 1.1(3) ?
F1 C5 C21 C26 . . . . 152.23(19) ?
C11 C5 C21 C26 . . . . -90.3(2) ?
C4 C5 C21 C26 . . . . 36.2(3) ?
F1 C5 C21 C22 . . . . -31.6(3) ?
C11 C5 C21 C22 . . . . 85.9(2) ?
C4 C5 C21 C22 . . . . -147.6(2) ?
C26 C21 C22 C23 . . . . -0.2(3) ?
C5 C21 C22 C23 . . . . -176.5(2) ?
C21 C22 C23 C24 . . . . -0.4(3) ?
C22 C23 C24 C25 . . . . 1.0(3) ?
C23 C24 C25 C26 . . . . -0.9(3) ?
C22 C21 C26 C25 . . . . 0.3(3) ?
C5 C21 C26 C25 . . . . 176.6(2) ?
C24 C25 C26 C21 . . . . 0.2(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1A F1 2_466 0.99 2.52 3.508(3) 174.4 ?


####################################################################### 
# 
# 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_gil7666
_database_code_depnum_ccdc_archive 'CCDC 1048076'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 F O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         304.36

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6630(3)
_cell_length_b                   9.5972(3)
_cell_length_c                   10.7876(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.646(2)
_cell_angle_gamma                90
_cell_volume                     1429.70(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3774
_cell_measurement_theta_min      3.2002
_cell_measurement_theta_max      66.4501
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'D8 Venture Dual Source'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10126
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             2456
_reflns_number_gt                1909
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0922
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         2456
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+1.0453P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.379
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)
;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.19272(9) 0.56536(13) 0.54639(11) 0.0188(3) Uani d . . . 1 . .
O O1 0.13456(12) 0.85290(17) 0.50119(15) 0.0232(4) Uani d . . . 1 . .
O O2 0.10765(12) 0.95265(16) 0.69648(15) 0.0225(4) Uani d . . . 1 . .
S S1 0.09748(4) 0.83669(6) 0.60791(5) 0.01460(16) Uani d . . . 1 . .
C C1 -0.02599(16) 0.7839(3) 0.5490(2) 0.0185(5) Uani d . . . 1 . .
H H1A -0.0696 0.8648 0.5407 0.022 Uiso calc U . R 1 . .
H H1B -0.0422 0.7374 0.4623 0.022 Uiso calc U . R 1 . .
C C2 -0.03404(15) 0.6828(2) 0.6535(2) 0.0170(5) Uani d . . . 1 . .
H H2A -0.0944 0.6275 0.6197 0.02 Uiso calc U . R 1 . .
H H2B -0.0344 0.7338 0.7331 0.02 Uiso calc U . R 1 . .
C C3 0.05478(15) 0.5878(2) 0.6856(2) 0.0164(5) Uani d . . . 1 . .
H H3A 0.0477 0.5224 0.612 0.02 Uiso calc U . R 1 . .
H H3B 0.0618 0.5329 0.7659 0.02 Uiso calc U . R 1 . .
C C4 0.14401(15) 0.6809(2) 0.7073(2) 0.0128(5) Uani d . . . 1 . .
H H4 0.1675 0.71 0.8018 0.015 Uiso calc U . R 1 . .
C C5 0.22834(16) 0.6098(2) 0.6794(2) 0.0138(5) Uani d . . . 1 . .
C C11 0.31570(15) 0.7025(2) 0.6941(2) 0.0144(5) Uani d . . . 1 . .
C C12 0.37723(16) 0.6683(3) 0.6247(2) 0.0185(5) Uani d . . . 1 . .
H H12 0.3633 0.5895 0.5681 0.022 Uiso calc U . R 1 . .
C C13 0.45843(17) 0.7479(3) 0.6374(2) 0.0243(6) Uani d . . . 1 . .
H H13 0.4993 0.7243 0.5885 0.029 Uiso calc U . R 1 . .
C C14 0.48044(17) 0.8616(3) 0.7209(2) 0.0248(6) Uani d . . . 1 . .
H H14 0.5365 0.916 0.7302 0.03 Uiso calc U . R 1 . .
C C15 0.42011(17) 0.8952(3) 0.7907(2) 0.0248(6) Uani d . . . 1 . .
H H15 0.435 0.9729 0.8487 0.03 Uiso calc U . R 1 . .
C C16 0.33781(16) 0.8168(2) 0.7771(2) 0.0202(5) Uani d . . . 1 . .
H H16 0.2964 0.8417 0.8249 0.024 Uiso calc U . R 1 . .
C C21 0.25761(15) 0.4790(2) 0.7644(2) 0.0138(5) Uani d . . . 1 . .
C C22 0.30197(16) 0.4916(3) 0.9002(2) 0.0196(5) Uani d . . . 1 . .
H H22 0.3149 0.5813 0.9395 0.024 Uiso calc U . R 1 . .
C C23 0.32715(17) 0.3732(3) 0.9779(2) 0.0230(6) Uani d . . . 1 . .
H H23 0.3577 0.3823 1.0704 0.028 Uiso calc U . R 1 . .
C C24 0.30828(17) 0.2421(3) 0.9221(2) 0.0226(6) Uani d . . . 1 . .
H H24 0.3252 0.1615 0.9761 0.027 Uiso calc U . R 1 . .
C C25 0.26486(16) 0.2287(3) 0.7877(2) 0.0218(6) Uani d . . . 1 . .
H H25 0.252 0.1388 0.749 0.026 Uiso calc U . R 1 . .
C C26 0.23987(15) 0.3469(2) 0.7090(2) 0.0179(5) Uani d . . . 1 . .
H H26 0.2104 0.3372 0.6164 0.021 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C5 . 1.418(2) ?
O1 S1 . 1.4374(16) ?
O2 S1 . 1.4415(16) ?
S1 C1 . 1.779(2) ?
S1 C4 . 1.832(2) ?
C1 C2 . 1.522(3) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.531(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.536(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.528(3) ?
C4 H4 . 1.0 ?
C5 C11 . 1.524(3) ?
C5 C21 . 1.528(3) ?
C11 C16 . 1.384(3) ?
C11 C12 . 1.391(3) ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.383(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.378(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.388(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.388(3) ?
C21 C22 . 1.395(3) ?
C22 C23 . 1.386(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.382(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.379(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.391(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 117.68(10) ?
O1 S1 C1 . . 111.00(10) ?
O2 S1 C1 . . 108.82(10) ?
O1 S1 C4 . . 112.96(10) ?
O2 S1 C4 . . 107.88(10) ?
C1 S1 C4 . . 96.37(10) ?
C2 C1 S1 . . 103.88(15) ?
C2 C1 H1A . . 111.0 ?
S1 C1 H1A . . 111.0 ?
C2 C1 H1B . . 111.0 ?
S1 C1 H1B . . 111.0 ?
H1A C1 H1B . . 109.0 ?
C1 C2 C3 . . 105.97(18) ?
C1 C2 H2A . . 110.5 ?
C3 C2 H2A . . 110.5 ?
C1 C2 H2B . . 110.5 ?
C3 C2 H2B . . 110.5 ?
H2A C2 H2B . . 108.7 ?
C2 C3 C4 . . 107.74(18) ?
C2 C3 H3A . . 110.2 ?
C4 C3 H3A . . 110.2 ?
C2 C3 H3B . . 110.2 ?
C4 C3 H3B . . 110.2 ?
H3A C3 H3B . . 108.5 ?
C5 C4 C3 . . 114.48(19) ?
C5 C4 S1 . . 114.60(15) ?
C3 C4 S1 . . 104.76(14) ?
C5 C4 H4 . . 107.5 ?
C3 C4 H4 . . 107.5 ?
S1 C4 H4 . . 107.5 ?
F1 C5 C11 . . 106.94(16) ?
F1 C5 C21 . . 107.09(17) ?
C11 C5 C21 . . 111.14(17) ?
F1 C5 C4 . . 106.64(17) ?
C11 C5 C4 . . 115.23(19) ?
C21 C5 C4 . . 109.37(17) ?
C16 C11 C12 . . 118.8(2) ?
C16 C11 C5 . . 122.4(2) ?
C12 C11 C5 . . 118.7(2) ?
C13 C12 C11 . . 120.6(2) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 120.4(2) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.2(2) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C14 C15 C16 . . 120.7(2) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C11 C16 C15 . . 120.3(2) ?
C11 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C26 C21 C22 . . 119.0(2) ?
C26 C21 C5 . . 121.17(19) ?
C22 C21 C5 . . 119.8(2) ?
C23 C22 C21 . . 120.0(2) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C24 C23 C22 . . 120.6(2) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C25 C24 C23 . . 119.8(2) ?
C25 C24 H24 . . 120.1 ?
C23 C24 H24 . . 120.1 ?
C24 C25 C26 . . 120.0(2) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C21 C26 C25 . . 120.6(2) ?
C21 C26 H26 . . 119.7 ?
C25 C26 H26 . . 119.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . 142.67(15) ?
O2 S1 C1 C2 . . . . -86.29(17) ?
C4 S1 C1 C2 . . . . 25.08(17) ?
S1 C1 C2 C3 . . . . -44.7(2) ?
C1 C2 C3 C4 . . . . 47.7(2) ?
C2 C3 C4 C5 . . . . -153.90(18) ?
C2 C3 C4 S1 . . . . -27.53(19) ?
O1 S1 C4 C5 . . . . 11.47(19) ?
O2 S1 C4 C5 . . . . -120.35(16) ?
C1 S1 C4 C5 . . . . 127.49(17) ?
O1 S1 C4 C3 . . . . -114.83(15) ?
O2 S1 C4 C3 . . . . 113.35(14) ?
C1 S1 C4 C3 . . . . 1.19(16) ?
C3 C4 C5 F1 . . . . 58.7(2) ?
S1 C4 C5 F1 . . . . -62.4(2) ?
C3 C4 C5 C11 . . . . 177.22(17) ?
S1 C4 C5 C11 . . . . 56.1(2) ?
C3 C4 C5 C21 . . . . -56.7(2) ?
S1 C4 C5 C21 . . . . -177.84(14) ?
F1 C5 C11 C16 . . . . 145.2(2) ?
C21 C5 C11 C16 . . . . -98.2(2) ?
C4 C5 C11 C16 . . . . 26.9(3) ?
F1 C5 C11 C12 . . . . -36.9(3) ?
C21 C5 C11 C12 . . . . 79.6(2) ?
C4 C5 C11 C12 . . . . -155.23(19) ?
C16 C11 C12 C13 . . . . -0.7(3) ?
C5 C11 C12 C13 . . . . -178.6(2) ?
C11 C12 C13 C14 . . . . 1.0(4) ?
C12 C13 C14 C15 . . . . -0.4(4) ?
C13 C14 C15 C16 . . . . -0.4(4) ?
C12 C11 C16 C15 . . . . -0.2(3) ?
C5 C11 C16 C15 . . . . 177.7(2) ?
C14 C15 C16 C11 . . . . 0.7(4) ?
F1 C5 C21 C26 . . . . -5.3(3) ?
C11 C5 C21 C26 . . . . -121.8(2) ?
C4 C5 C21 C26 . . . . 109.8(2) ?
F1 C5 C21 C22 . . . . 175.40(18) ?
C11 C5 C21 C22 . . . . 58.9(3) ?
C4 C5 C21 C22 . . . . -69.4(2) ?
C26 C21 C22 C23 . . . . -0.4(3) ?
C5 C21 C22 C23 . . . . 178.9(2) ?
C21 C22 C23 C24 . . . . -0.3(3) ?
C22 C23 C24 C25 . . . . 0.6(4) ?
C23 C24 C25 C26 . . . . -0.3(3) ?
C22 C21 C26 C25 . . . . 0.7(3) ?
C5 C21 C26 C25 . . . . -178.5(2) ?
C24 C25 C26 C21 . . . . -0.4(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O1 4_576 1.00 2.43 3.236(3) 136.8 ?
####################################################################### 
# 
# 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_gil7899
_database_code_depnum_ccdc_archive 'CCDC 1048077'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 F N O3 S'
_chemical_formula_weight         217.21
_chemical_absolute_configuration .

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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'

_cell_length_a                   20.3421(7)
_cell_length_b                   4.6595(2)
_cell_length_c                   9.8133(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     930.14(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1685
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      25.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8472
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7714
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.49
_diffrn_reflns_theta_max         25.57
_reflns_number_total             1589
_reflns_number_gt                1195
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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. 

 The molecule is disordered over two positions. Several restraints (SADI,
 SAME, ISOR and SIMU) were used in order to improve refinement stability.

 The structure was refined using the 'TWIN' option, whereby the BASF 
 factor was refined to 0.35.
;

_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)+(0.0533P)²+1.1342P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_number_reflns         1589
_refine_ls_number_parameters     193
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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
C3 C 0.42307(19) 0.7505(8) 0.5039(13) 0.0563(12) Uani 1 1 d D . .
C1 C 0.6204(6) 0.872(3) 0.5268(19) 0.057(4) Uani 0.584(11) 1 d PDU A 1
H1A H 0.6255 0.9557 0.6179 0.069 Uiso 0.584(11) 1 calc PR A 1
H1B H 0.6532 0.7195 0.5170 0.069 Uiso 0.584(11) 1 calc PR A 1
F1 F 0.6325(5) 1.083(2) 0.4296(11) 0.087(3) Uani 0.584(11) 1 d PDU A 1
C2 C 0.5540(5) 0.746(3) 0.5152(17) 0.041(4) Uani 0.584(11) 1 d PDU A 1
H2A H 0.5479 0.6062 0.5888 0.049 Uiso 0.584(11) 1 calc PR A 1
H2B H 0.5509 0.6421 0.4286 0.049 Uiso 0.584(11) 1 calc PR A 1
S1 S 0.4899(3) 1.0003(11) 0.5230(5) 0.0505(13) Uani 0.584(11) 1 d PDU A 1
O1 O 0.4977(5) 1.096(2) 0.6652(10) 0.068(3) Uani 0.584(11) 1 d PDU A 1
C1A C 0.6197(8) 0.878(4) 0.478(2) 0.047(5) Uani 0.416(11) 1 d PDU A 2
H1A1 H 0.6506 0.7382 0.5167 0.056 Uiso 0.416(11) 1 calc PR A 2
H1A2 H 0.6332 0.9123 0.3834 0.056 Uiso 0.416(11) 1 calc PR A 2
F1A F 0.6260(5) 1.134(2) 0.5498(13) 0.068(4) Uani 0.416(11) 1 d PDU A 2
C2A C 0.5541(7) 0.747(4) 0.476(2) 0.044(5) Uani 0.416(11) 1 d PDU A 2
H2A1 H 0.5483 0.6345 0.5596 0.053 Uiso 0.416(11) 1 calc PR A 2
H2A2 H 0.5513 0.6146 0.3988 0.053 Uiso 0.416(11) 1 calc PR A 2
S1A S 0.4891(4) 0.9968(18) 0.4639(7) 0.052(2) Uani 0.416(11) 1 d PDU A 2
O1A O 0.4965(6) 1.048(3) 0.3132(11) 0.067(4) Uani 0.416(11) 1 d PDU A 2
C4 C 0.3970(4) 0.6628(18) 0.6217(11) 0.061(2) Uani 1 1 d . A .
H4 H 0.4140 0.7337 0.7042 0.074 Uiso 1 1 calc R . .
C5 C 0.3464(4) 0.4724(16) 0.6241(9) 0.055(2) Uani 1 1 d . . .
H5 H 0.3286 0.4098 0.7075 0.066 Uiso 1 1 calc R A .
C6 C 0.32218(17) 0.3759(8) 0.5060(12) 0.0460(9) Uani 1 1 d . A .
C7 C 0.3470(4) 0.4594(17) 0.3826(9) 0.061(2) Uani 1 1 d . . .
H7 H 0.3296 0.3868 0.3009 0.073 Uiso 1 1 calc R A .
C8 C 0.3991(5) 0.6555(18) 0.3812(10) 0.067(2) Uani 1 1 d . A .
H8 H 0.4172 0.7204 0.2985 0.080 Uiso 1 1 calc R . .
N1 N 0.26885(15) 0.1652(8) 0.5029(10) 0.0590(10) Uani 1 1 d D . .
O2 O 0.2367(10) 0.173(6) 0.6130(16) 0.058(6) Uani 0.29(3) 1 d PDU A 1
O3 O 0.2575(11) -0.002(4) 0.417(2) 0.054(6) Uani 0.29(3) 1 d PDU A 1
O2A O 0.2522(6) 0.053(3) 0.6051(11) 0.071(3) Uani 0.71(3) 1 d PDU A 2
O3A O 0.2456(6) 0.105(3) 0.3870(11) 0.086(4) Uani 0.71(3) 1 d PDU A 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
C3 C4 1.335(13) . ?
C3 C8 1.373(13) . ?
C3 S1 1.799(6) . ?
C3 S1A 1.810(9) . ?
C1 F1 1.392(12) . ?
C1 C2 1.478(11) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 S1 1.764(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
S1 O1 1.473(10) . ?
C1A F1A 1.394(14) . ?
C1A C2A 1.468(13) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C2A S1A 1.764(13) . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
S1A O1A 1.505(12) . ?
C4 C5 1.360(10) . ?
C4 H4 0.9400 . ?
C5 C6 1.337(12) . ?
C5 H5 0.9400 . ?
C6 C7 1.369(12) . ?
C6 N1 1.464(5) . ?
C7 C8 1.399(11) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
N1 O3 1.169(12) . ?
N1 O2A 1.181(9) . ?
N1 O3A 1.263(10) . ?
N1 O2 1.263(13) . ?

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
C4 C3 C8 121.3(4) . . ?
C4 C3 S1 114.0(8) . . ?
C8 C3 S1 124.6(8) . . ?
C4 C3 S1A 132.5(8) . . ?
C8 C3 S1A 106.1(8) . . ?
S1 C3 S1A 18.50(18) . . ?
F1 C1 C2 113.0(12) . . ?
F1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
F1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 S1 113.9(9) . . ?
C1 C2 H2A 108.8 . . ?
S1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
S1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
O1 S1 C2 99.5(7) . . ?
O1 S1 C3 112.1(7) . . ?
C2 S1 C3 96.8(5) . . ?
F1A C1A C2A 116.3(14) . . ?
F1A C1A H1A1 108.2 . . ?
C2A C1A H1A1 108.2 . . ?
F1A C1A H1A2 108.2 . . ?
C2A C1A H1A2 108.2 . . ?
H1A1 C1A H1A2 107.4 . . ?
C1A C2A S1A 114.2(13) . . ?
C1A C2A H2A1 108.7 . . ?
S1A C2A H2A1 108.7 . . ?
C1A C2A H2A2 108.7 . . ?
S1A C2A H2A2 108.7 . . ?
H2A1 C2A H2A2 107.6 . . ?
O1A S1A C2A 95.6(10) . . ?
O1A S1A C3 112.8(8) . . ?
C2A S1A C3 97.1(7) . . ?
C3 C4 C5 121.0(8) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.8(8) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 122.4(4) . . ?
C5 C6 N1 121.1(7) . . ?
C7 C6 N1 116.5(7) . . ?
C6 C7 C8 118.3(8) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C3 C8 C7 118.1(7) . . ?
C3 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
O3 N1 O2A 104.9(11) . . ?
O3 N1 O3A 29.8(10) . . ?
O2A N1 O3A 124.0(7) . . ?
O3 N1 O2 122.1(13) . . ?
O2A N1 O2 30.5(10) . . ?
O3A N1 O2 125.6(9) . . ?
O3 N1 C6 127.5(12) . . ?
O2A N1 C6 119.5(8) . . ?
O3A N1 C6 116.4(8) . . ?
O2 N1 C6 110.3(11) . . ?

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
F1 C1 C2 S1 -56(2) . . . . ?
C1 C2 S1 O1 -66.6(14) . . . . ?
C1 C2 S1 C3 179.6(12) . . . . ?
C4 C3 S1 O1 -8.3(8) . . . . ?
C8 C3 S1 O1 171.1(7) . . . . ?
S1A C3 S1 O1 170.3(17) . . . . ?
C4 C3 S1 C2 94.8(7) . . . . ?
C8 C3 S1 C2 -85.8(8) . . . . ?
S1A C3 S1 C2 -86.5(15) . . . . ?
F1A C1A C2A S1A 38(3) . . . . ?
C1A C2A S1A O1A 78.2(18) . . . . ?
C1A C2A S1A C3 -167.9(17) . . . . ?
C4 C3 S1A O1A -174.6(8) . . . . ?
C8 C3 S1A O1A 4.4(9) . . . . ?
S1 C3 S1A O1A -176.2(19) . . . . ?
C4 C3 S1A C2A 86.3(10) . . . . ?
C8 C3 S1A C2A -94.7(10) . . . . ?
S1 C3 S1A C2A 84.7(15) . . . . ?
C8 C3 C4 C5 1.0(8) . . . . ?
S1 C3 C4 C5 -179.6(6) . . . . ?
S1A C3 C4 C5 179.8(6) . . . . ?
C3 C4 C5 C6 -0.8(11) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C4 C5 C6 N1 178.4(5) . . . . ?
C5 C6 C7 C8 -0.8(8) . . . . ?
N1 C6 C7 C8 -178.5(6) . . . . ?
C4 C3 C8 C7 -1.0(8) . . . . ?
S1 C3 C8 C7 179.6(6) . . . . ?
S1A C3 C8 C7 179.9(7) . . . . ?
C6 C7 C8 C3 0.9(11) . . . . ?
C5 C6 N1 O3 -153.0(16) . . . . ?
C7 C6 N1 O3 24.8(17) . . . . ?
C5 C6 N1 O2A -9.2(11) . . . . ?
C7 C6 N1 O2A 168.6(10) . . . . ?
C5 C6 N1 O3A 174.2(9) . . . . ?
C7 C6 N1 O3A -8.0(10) . . . . ?
C5 C6 N1 O2 23.0(15) . . . . ?
C7 C6 N1 O2 -159.3(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.57
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_gil7727
_database_code_depnum_ccdc_archive 'CCDC 1048078'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 F N O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         233.21

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2161(3)
_cell_length_b                   7.3574(3)
_cell_length_c                   9.1736(4)
_cell_angle_alpha                86.0450(12)
_cell_angle_beta                 76.9930(12)
_cell_angle_gamma                78.2660(12)
_cell_volume                     464.49(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9733
_cell_measurement_theta_min      4.9494
_cell_measurement_theta_max      68.3167
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.086
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240

_exptl_absorpt_coefficient_mu    3.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.77

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            11607
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_theta_min         4.95
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             1699
_reflns_number_gt                1631
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0753
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         1699
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+0.3353P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.71804(5) 0.55995(5) 0.14876(4) 0.01351(13) Uani d . . . 1 . .
F F1 0.58452(14) 1.00002(12) 0.15605(10) 0.0217(2) Uani d . . . 1 . .
N N1 0.02279(19) 0.82549(18) 0.62830(14) 0.0175(3) Uani d . . . 1 . .
O O1 0.88913(15) 0.54856(16) 0.20828(12) 0.0184(3) Uani d . . . 1 . .
O O2 0.68741(16) 0.39529(15) 0.08872(12) 0.0181(3) Uani d . . . 1 . .
O O3 -0.13232(16) 0.78797(18) 0.61876(13) 0.0253(3) Uani d . . . 1 . .
O O4 0.04148(17) 0.91636(17) 0.72916(13) 0.0250(3) Uani d . . . 1 . .
C C1 0.7460(2) 0.9191(2) 0.04853(18) 0.0192(3) Uani d . . . 1 . .
H H1A 0.8642 0.9005 0.0899 0.023 Uiso calc U . R 1 . .
H H1B 0.7636 1.0025 -0.0408 0.023 Uiso calc U . R 1 . .
C C2 0.7163(2) 0.7349(2) 0.00492(17) 0.0161(3) Uani d . . . 1 . .
H H2A 0.8196 0.6898 -0.0829 0.019 Uiso calc U . R 1 . .
H H2B 0.5907 0.7542 -0.026 0.019 Uiso calc U . R 1 . .
C C3 0.5129(2) 0.6399(2) 0.29329(17) 0.0142(3) Uani d . . . 1 . .
C C4 0.3324(2) 0.6186(2) 0.27576(17) 0.0176(3) Uani d . . . 1 . .
H H4 0.3201 0.564 0.1884 0.021 Uiso calc U . R 1 . .
C C5 0.1706(2) 0.6780(2) 0.38722(18) 0.0176(3) Uani d . . . 1 . .
H H5 0.0456 0.6639 0.3787 0.021 Uiso calc U . R 1 . .
C C6 0.1961(2) 0.7586(2) 0.51145(17) 0.0153(3) Uani d . . . 1 . .
C C7 0.3751(2) 0.7814(2) 0.53088(17) 0.0160(3) Uani d . . . 1 . .
H H7 0.3867 0.8371 0.618 0.019 Uiso calc U . R 1 . .
C C8 0.5366(2) 0.7202(2) 0.41910(17) 0.0158(3) Uani d . . . 1 . .
H H8 0.6618 0.733 0.4284 0.019 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.4407(11) ?
S1 O1 . 1.4438(11) ?
S1 C2 . 1.7789(15) ?
S1 C3 . 1.7791(15) ?
F1 C1 . 1.4024(18) ?
N1 O4 . 1.2246(17) ?
N1 O3 . 1.2287(18) ?
N1 C6 . 1.474(2) ?
C1 C2 . 1.508(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.388(2) ?
C3 C8 . 1.391(2) ?
C4 C5 . 1.384(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.384(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.387(2) ?
C7 C8 . 1.388(2) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 118.58(7) ?
O2 S1 C2 . . 107.16(7) ?
O1 S1 C2 . . 108.91(7) ?
O2 S1 C3 . . 108.01(7) ?
O1 S1 C3 . . 107.66(7) ?
C2 S1 C3 . . 105.83(7) ?
O4 N1 O3 . . 123.65(13) ?
O4 N1 C6 . . 118.03(13) ?
O3 N1 C6 . . 118.32(13) ?
F1 C1 C2 . . 109.54(12) ?
F1 C1 H1A . . 109.8 ?
C2 C1 H1A . . 109.8 ?
F1 C1 H1B . . 109.8 ?
C2 C1 H1B . . 109.8 ?
H1A C1 H1B . . 108.2 ?
C1 C2 S1 . . 114.53(11) ?
C1 C2 H2A . . 108.6 ?
S1 C2 H2A . . 108.6 ?
C1 C2 H2B . . 108.6 ?
S1 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.6 ?
C4 C3 C8 . . 122.11(14) ?
C4 C3 S1 . . 117.97(11) ?
C8 C3 S1 . . 119.91(12) ?
C5 C4 C3 . . 119.14(14) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C6 C5 C4 . . 118.19(14) ?
C6 C5 H5 . . 120.9 ?
C4 C5 H5 . . 120.9 ?
C5 C6 C7 . . 123.52(14) ?
C5 C6 N1 . . 117.99(14) ?
C7 C6 N1 . . 118.48(13) ?
C6 C7 C8 . . 117.90(14) ?
C6 C7 H7 . . 121.0 ?
C8 C7 H7 . . 121.0 ?
C7 C8 C3 . . 119.13(14) ?
C7 C8 H8 . . 120.4 ?
C3 C8 H8 . . 120.4 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 S1 . . . . -68.12(15) ?
O2 S1 C2 C1 . . . . 179.82(10) ?
O1 S1 C2 C1 . . . . -50.76(13) ?
C3 S1 C2 C1 . . . . 64.74(13) ?
O2 S1 C3 C4 . . . . -35.20(14) ?
O1 S1 C3 C4 . . . . -164.36(12) ?
C2 S1 C3 C4 . . . . 79.29(13) ?
O2 S1 C3 C8 . . . . 144.62(12) ?
O1 S1 C3 C8 . . . . 15.46(14) ?
C2 S1 C3 C8 . . . . -100.88(13) ?
C8 C3 C4 C5 . . . . -0.4(2) ?
S1 C3 C4 C5 . . . . 179.40(12) ?
C3 C4 C5 C6 . . . . 0.7(2) ?
C4 C5 C6 C7 . . . . -0.6(2) ?
C4 C5 C6 N1 . . . . 178.66(13) ?
O4 N1 C6 C5 . . . . -171.42(14) ?
O3 N1 C6 C5 . . . . 8.2(2) ?
O4 N1 C6 C7 . . . . 7.9(2) ?
O3 N1 C6 C7 . . . . -172.47(14) ?
C5 C6 C7 C8 . . . . 0.2(2) ?
N1 C6 C7 C8 . . . . -179.11(13) ?
C6 C7 C8 C3 . . . . 0.2(2) ?
C4 C3 C8 C7 . . . . 0.0(2) ?
S1 C3 C8 C7 . . . . -179.86(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1A O4 2_676 0.99 2.50 3.237(2) 131.5 ?
C1 H1B O4 1_654 0.99 2.58 3.211(2) 121.8 ?
C2 H2B F1 2_675 0.99 2.40 3.1656(18) 134.0 ?
C4 H4 O2 2_665 0.95 2.55 3.3881(19) 147.1 ?
C5 H5 O1 1_455 0.95 2.41 3.1989(19) 140.4 ?
C7 H7 F1 2_676 0.95 2.53 3.4822(18) 177.4 ?



#=============================================================================
#  end of cif data for "gil7727" (compound 7) 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

