# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_170526e
_database_code_depnum_ccdc_archive 'CCDC 1578941'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Br F N O4 S'
_chemical_formula_weight         338.15

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.7382(6)
_cell_length_b                   5.8569(4)
_cell_length_c                   23.8346(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.1410(10)
_cell_angle_gamma                90.00
_cell_volume                     1219.58(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2003
_cell_measurement_theta_min      2.499
_cell_measurement_theta_max      24.23

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    3.560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3301
_exptl_absorpt_correction_T_max  0.4948
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5749
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2143
_reflns_number_gt                1564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0447P)²+0.5363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2143
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.90870(5) 1.32231(8) 0.04779(2) 0.0653(2) Uani 1 1 d . . .
F1 F 0.5730(5) 0.8440(5) 0.29553(12) 0.1118(12) Uani 1 1 d . . .
N1 N 0.3051(3) 0.8412(5) 0.13453(14) 0.0466(8) Uani 1 1 d . . .
O1 O 0.3187(3) 0.5201(5) 0.07939(12) 0.0552(7) Uani 1 1 d . . .
O2 O 0.1812(3) 0.7716(5) 0.16576(11) 0.0484(7) Uani 1 1 d . . .
O3 O 0.7010(4) 0.8309(7) 0.21164(17) 0.1015(14) Uani 1 1 d . . .
O4 O 0.4784(5) 0.6005(5) 0.2246(2) 0.1144(16) Uani 1 1 d . . .
S1 S 0.55278(13) 0.80470(18) 0.23424(5) 0.0519(3) Uani 1 1 d . . .
C1 C 0.3683(4) 0.7039(7) 0.09554(16) 0.0401(9) Uani 1 1 d . . .
C2 C 0.5057(4) 0.8308(6) 0.07800(15) 0.0360(8) Uani 1 1 d . . .
C3 C 0.6088(4) 0.7808(7) 0.03664(16) 0.0452(10) Uani 1 1 d . . .
H3 H 0.5976 0.6494 0.0150 0.054 Uiso 1 1 calc R . .
C4 C 0.7281(4) 0.9281(7) 0.02800(16) 0.0457(9) Uani 1 1 d . . .
H4 H 0.7998 0.8969 0.0007 0.055 Uiso 1 1 calc R . .
C5 C 0.7406(4) 1.1222(7) 0.06012(16) 0.0433(10) Uani 1 1 d . . .
C6 C 0.6396(4) 1.1778(6) 0.10158(15) 0.0409(9) Uani 1 1 d . . .
H6 H 0.6510 1.3101 0.1228 0.049 Uiso 1 1 calc R . .
C7 C 0.5212(4) 1.0285(6) 0.11003(14) 0.0362(8) Uani 1 1 d . . .
C8 C 0.3923(4) 1.0412(6) 0.15151(15) 0.0386(9) Uani 1 1 d . . .
H8 H 0.3312 1.1783 0.1438 0.046 Uiso 1 1 calc R . .
C9 C 0.4404(4) 1.0394(6) 0.21325(15) 0.0459(10) Uani 1 1 d . . .
H9A H 0.3489 1.0419 0.2356 0.055 Uiso 1 1 calc R . .
H9B H 0.4972 1.1781 0.2214 0.055 Uiso 1 1 calc R . .
C10 C 0.0420(5) 0.8374(8) 0.1382(2) 0.0650(13) Uani 1 1 d . . .
H10A H 0.0428 0.9992 0.1317 0.098 Uiso 1 1 calc R . .
H10B H -0.0428 0.7988 0.1614 0.098 Uiso 1 1 calc R . .
H10C H 0.0322 0.7587 0.1030 0.098 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
Br1 C5 1.906(4) . ?
F1 S1 1.486(3) . ?
N1 C1 1.355(5) . ?
N1 O2 1.387(4) . ?
N1 C8 1.451(5) . ?
O1 C1 1.220(4) . ?
O2 C10 1.424(5) . ?
O3 S1 1.421(3) . ?
O4 S1 1.378(3) . ?
S1 C9 1.756(4) . ?
C1 C2 1.479(5) . ?
C2 C3 1.380(5) . ?
C2 C7 1.392(5) . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(5) . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.515(4) . ?
C8 C9 1.522(5) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 N1 O2 121.8(3) . . ?
C1 N1 C8 116.8(3) . . ?
O2 N1 C8 119.9(3) . . ?
N1 O2 C10 110.0(3) . . ?
O4 S1 O3 117.5(3) . . ?
O4 S1 F1 110.2(3) . . ?
O3 S1 F1 105.3(3) . . ?
O4 S1 C9 111.9(2) . . ?
O3 S1 C9 108.4(2) . . ?
F1 S1 C9 102.35(18) . . ?
O1 C1 N1 126.3(3) . . ?
O1 C1 C2 129.8(3) . . ?
N1 C1 C2 103.9(3) . . ?
C3 C2 C7 120.7(3) . . ?
C3 C2 C1 129.8(3) . . ?
C7 C2 C1 109.5(3) . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 123.4(4) . . ?
C4 C5 Br1 118.4(3) . . ?
C6 C5 Br1 118.2(3) . . ?
C7 C6 C5 116.8(4) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
C6 C7 C2 121.0(3) . . ?
C6 C7 C8 129.5(3) . . ?
C2 C7 C8 109.5(3) . . ?
N1 C8 C7 99.9(3) . . ?
N1 C8 C9 113.4(3) . . ?
C7 C8 C9 115.9(3) . . ?
N1 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C8 C9 S1 115.0(3) . . ?
C8 C9 H9A 108.5 . . ?
S1 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
S1 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 O2 C10 -91.5(4) . . . . ?
C8 N1 O2 C10 102.7(4) . . . . ?
O2 N1 C1 O1 7.5(6) . . . . ?
C8 N1 C1 O1 173.8(4) . . . . ?
O2 N1 C1 C2 -173.1(3) . . . . ?
C8 N1 C1 C2 -6.9(4) . . . . ?
O1 C1 C2 C3 4.1(7) . . . . ?
N1 C1 C2 C3 -175.2(4) . . . . ?
O1 C1 C2 C7 -177.0(4) . . . . ?
N1 C1 C2 C7 3.7(4) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C4 179.6(4) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C3 C4 C5 Br1 179.3(3) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
Br1 C5 C6 C7 -179.0(3) . . . . ?
C5 C6 C7 C2 0.1(5) . . . . ?
C5 C6 C7 C8 -179.6(4) . . . . ?
C3 C2 C7 C6 -0.4(5) . . . . ?
C1 C2 C7 C6 -179.4(3) . . . . ?
C3 C2 C7 C8 179.4(3) . . . . ?
C1 C2 C7 C8 0.4(4) . . . . ?
C1 N1 C8 C7 7.0(4) . . . . ?
O2 N1 C8 C7 173.5(3) . . . . ?
C1 N1 C8 C9 -117.0(4) . . . . ?
O2 N1 C8 C9 49.5(4) . . . . ?
C6 C7 C8 N1 175.8(4) . . . . ?
C2 C7 C8 N1 -4.0(4) . . . . ?
C6 C7 C8 C9 -62.1(5) . . . . ?
C2 C7 C8 C9 118.2(3) . . . . ?
N1 C8 C9 S1 58.7(4) . . . . ?
C7 C8 C9 S1 -56.0(4) . . . . ?
O4 S1 C9 C8 -59.1(4) . . . . ?
O3 S1 C9 C8 72.0(3) . . . . ?
F1 S1 C9 C8 -177.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_170906f
_database_code_depnum_ccdc_archive 'CCDC 1579682'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2018-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 F O5 S'
_chemical_formula_weight         322.30

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.6492(9)
_cell_length_b                   6.7929(8)
_cell_length_c                   25.645(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.112(2)
_cell_angle_gamma                90.00
_cell_volume                     1491.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2743
_cell_measurement_theta_min      2.675
_cell_measurement_theta_max      23.763

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9029
_exptl_absorpt_correction_T_max  0.9182
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2570
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2570
_reflns_number_gt                1863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1098P)²+1.9743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0813
_refine_ls_wR_factor_ref         0.2291
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O4 O 0.7330(6) 0.7871(9) 1.10163(18) 0.0999(19) Uani 1 1 d . . .
O1 O 0.7415(4) 0.9537(5) 0.99128(14) 0.0530(9) Uani 1 1 d . . .
O2 O 0.8862(4) 1.2054(5) 0.96973(15) 0.0605(10) Uani 1 1 d . . .
O3 O 0.8863(7) 0.4339(6) 0.81989(18) 0.0914(16) Uani 1 1 d . . .
F1 F 0.5021(5) 0.6488(8) 1.05511(16) 0.1036(15) Uani 1 1 d . . .
O5 O 0.7021(7) 0.4405(9) 1.0990(2) 0.113(2) Uani 1 1 d . . .
S1 S 0.66303(16) 0.6233(2) 1.07018(5) 0.0583(5) Uani 1 1 d . . .
C1 C 0.8385(6) 1.0420(7) 0.95994(19) 0.0457(11) Uani 1 1 d . . .
C2 C 0.8645(5) 0.9065(7) 0.91889(19) 0.0443(11) Uani 1 1 d . . .
C3 C 0.9538(6) 0.9262(8) 0.8782(2) 0.0551(13) Uani 1 1 d . . .
H3 H 1.0065 1.0432 0.8739 0.066 Uiso 1 1 calc R . .
C4 C 0.9636(7) 0.7730(9) 0.8445(2) 0.0609(15) Uani 1 1 d . . .
H4 H 1.0250 0.7832 0.8177 0.073 Uiso 1 1 calc R . .
C5 C 0.8796(7) 0.5988(8) 0.8509(2) 0.0588(14) Uani 1 1 d . . .
C6 C 0.7901(6) 0.5765(7) 0.89046(19) 0.0527(13) Uani 1 1 d . . .
H6 H 0.7360 0.4604 0.8945 0.063 Uiso 1 1 calc R . .
C7 C 0.7837(5) 0.7350(7) 0.92431(17) 0.0428(11) Uani 1 1 d . . .
C8 C 0.7029(6) 0.7553(7) 0.97240(18) 0.0448(11) Uani 1 1 d . . .
H8 H 0.5897 0.7417 0.9627 0.054 Uiso 1 1 calc R . .
C9 C 0.7619(6) 0.6089(7) 1.01482(18) 0.0462(11) Uani 1 1 d . . .
H9A H 0.8724 0.6317 1.0259 0.055 Uiso 1 1 calc R . .
H9B H 0.7502 0.4770 1.0003 0.055 Uiso 1 1 calc R . .
C10 C 0.9485(7) 0.4397(9) 0.7727(2) 0.0604(15) Uani 1 1 d . . .
C11 C 0.8937(8) 0.5588(10) 0.7321(3) 0.0796(19) Uani 1 1 d . . .
H11 H 0.8142 0.6482 0.7355 0.095 Uiso 1 1 calc R . .
C12 C 0.9566(11) 0.5472(12) 0.6850(3) 0.091(2) Uani 1 1 d . . .
H12 H 0.9224 0.6326 0.6574 0.110 Uiso 1 1 calc R . .
C13 C 1.0662(11) 0.4130(12) 0.6797(3) 0.093(2) Uani 1 1 d . . .
H13 H 1.1057 0.4024 0.6479 0.111 Uiso 1 1 calc R . .
C14 C 1.1203(10) 0.2925(12) 0.7202(3) 0.097(3) Uani 1 1 d . . .
H14 H 1.1959 0.1987 0.7160 0.117 Uiso 1 1 calc R . .
C15 C 1.0641(8) 0.3080(10) 0.7676(2) 0.0766(18) Uani 1 1 d . . .
H15 H 1.1047 0.2292 0.7959 0.092 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
O4 S1 1.455(4) . ?
O1 C1 1.378(6) . ?
O1 C8 1.455(6) . ?
O2 C1 1.198(6) . ?
O3 C5 1.379(6) . ?
O3 C10 1.392(6) . ?
F1 S1 1.402(4) . ?
O5 S1 1.461(5) . ?
S1 C9 1.760(5) . ?
C1 C2 1.440(7) . ?
C2 C7 1.376(6) . ?
C2 C3 1.391(7) . ?
C3 C4 1.361(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(7) . ?
C6 C7 1.389(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.507(6) . ?
C8 C9 1.508(7) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.351(9) . ?
C10 C15 1.362(9) . ?
C11 C12 1.395(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.336(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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 O1 C8 109.8(4) . . ?
C5 O3 C10 122.0(4) . . ?
F1 S1 O4 112.2(3) . . ?
F1 S1 O5 113.2(3) . . ?
O4 S1 O5 108.7(4) . . ?
F1 S1 C9 111.2(2) . . ?
O4 S1 C9 106.2(3) . . ?
O5 S1 C9 104.9(3) . . ?
O2 C1 O1 120.0(5) . . ?
O2 C1 C2 131.3(5) . . ?
O1 C1 C2 108.6(4) . . ?
C7 C2 C3 120.1(4) . . ?
C7 C2 C1 109.5(4) . . ?
C3 C2 C1 130.4(4) . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 O3 114.3(4) . . ?
C6 C5 C4 122.2(5) . . ?
O3 C5 C4 123.4(4) . . ?
C5 C6 C7 117.0(4) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
C2 C7 C6 121.9(4) . . ?
C2 C7 C8 107.8(4) . . ?
C6 C7 C8 130.2(4) . . ?
O1 C8 C7 104.2(4) . . ?
O1 C8 C9 109.4(4) . . ?
C7 C8 C9 112.4(4) . . ?
O1 C8 H8 110.2 . . ?
C7 C8 H8 110.2 . . ?
C9 C8 H8 110.2 . . ?
C8 C9 S1 113.0(3) . . ?
C8 C9 H9A 109.0 . . ?
S1 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
S1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 120.1(5) . . ?
C11 C10 O3 123.4(6) . . ?
C15 C10 O3 116.4(6) . . ?
C10 C11 C12 119.7(7) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.7(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.5(6) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120.3(7) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.4(7) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?

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
C8 O1 C1 O2 -178.5(4) . . . . ?
C8 O1 C1 C2 1.1(5) . . . . ?
O2 C1 C2 C7 179.9(5) . . . . ?
O1 C1 C2 C7 0.3(5) . . . . ?
O2 C1 C2 C3 0.0(9) . . . . ?
O1 C1 C2 C3 -179.5(5) . . . . ?
C7 C2 C3 C4 -1.6(8) . . . . ?
C1 C2 C3 C4 178.3(5) . . . . ?
C2 C3 C4 C5 1.6(9) . . . . ?
C10 O3 C5 C6 168.6(6) . . . . ?
C10 O3 C5 C4 -14.5(10) . . . . ?
C3 C4 C5 C6 -1.2(10) . . . . ?
C3 C4 C5 O3 -177.8(6) . . . . ?
O3 C5 C6 C7 177.6(5) . . . . ?
C4 C5 C6 C7 0.7(9) . . . . ?
C3 C2 C7 C6 1.1(8) . . . . ?
C1 C2 C7 C6 -178.8(5) . . . . ?
C3 C2 C7 C8 178.3(5) . . . . ?
C1 C2 C7 C8 -1.6(5) . . . . ?
C5 C6 C7 C2 -0.6(8) . . . . ?
C5 C6 C7 C8 -177.1(5) . . . . ?
C1 O1 C8 C7 -2.0(5) . . . . ?
C1 O1 C8 C9 118.5(4) . . . . ?
C2 C7 C8 O1 2.1(5) . . . . ?
C6 C7 C8 O1 179.0(5) . . . . ?
C2 C7 C8 C9 -116.2(5) . . . . ?
C6 C7 C8 C9 60.7(7) . . . . ?
O1 C8 C9 S1 67.3(4) . . . . ?
C7 C8 C9 S1 -177.4(3) . . . . ?
F1 S1 C9 C8 41.4(5) . . . . ?
O4 S1 C9 C8 -80.8(5) . . . . ?
O5 S1 C9 C8 164.2(4) . . . . ?
C5 O3 C10 C11 -58.2(9) . . . . ?
C5 O3 C10 C15 125.8(7) . . . . ?
C15 C10 C11 C12 -0.4(10) . . . . ?
O3 C10 C11 C12 -176.2(6) . . . . ?
C10 C11 C12 C13 2.7(12) . . . . ?
C11 C12 C13 C14 -2.1(13) . . . . ?
C12 C13 C14 C15 -0.7(13) . . . . ?
C11 C10 C15 C14 -2.3(11) . . . . ?
O3 C10 C15 C14 173.7(7) . . . . ?
C13 C14 C15 C10 2.9(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.075
