# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1973270'
loop_
_audit_author_name
_audit_author_address
'Xin Huang'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-02-20 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 H18 F2 O2 S'
_chemical_formula_weight         324.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.497(3)
_cell_length_b                   13.357(5)
_cell_length_c                   13.775(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 85.689(14)
_cell_angle_gamma                90.00
_cell_volume                     1559.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2243
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .28
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .954
_exptl_absorpt_correction_T_max  .975


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(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  'APES-\/cò CCDC'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6417
_diffrn_reflns_av_R_equivalents  0.1576
_diffrn_reflns_av_sigmaI/netI    0.1254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         22.13
_reflns_number_total             1895
_reflns_number_gt                968
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.0801P)²+0.0000P] 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         1895
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.1540
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2022
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.7006(3) 0.06132(17) 0.59289(15) 0.0757(8) Uani 1 1 d . . .
F1 F 0.6628(5) -0.0291(3) 0.8040(3) 0.0561(12) Uani 1 1 d . . .
O2 O 0.8660(5) 0.0599(3) 0.9275(3) 0.0452(13) Uani 1 1 d . . .
F2 F 0.8634(5) -0.1096(3) 0.7344(3) 0.0643(13) Uani 1 1 d . . .
O1 O 1.0445(5) -0.0663(3) 0.8774(3) 0.0526(14) Uani 1 1 d . . .
H1A H 1.0862 -0.0672 0.9292 0.079 Uiso 1 1 calc R . .
C5 C 0.7945(8) -0.1107(5) 0.9612(4) 0.0401(18) Uani 1 1 d . . .
C6 C 0.7620(9) -0.2775(6) 1.0247(5) 0.058(2) Uani 1 1 d . . .
H6A H 0.7939 -0.3442 1.0246 0.069 Uiso 1 1 calc R . .
C7 C 0.6685(9) -0.0796(6) 1.0229(5) 0.054(2) Uani 1 1 d . . .
H7A H 0.6361 -0.0131 1.0227 0.065 Uiso 1 1 calc R . .
C8 C 0.8864(9) -0.0403(5) 0.8943(5) 0.0457(19) Uani 1 1 d . . .
C9 C 0.8399(8) -0.2091(6) 0.9627(5) 0.0470(19) Uani 1 1 d . . .
H9A H 0.9248 -0.2303 0.9213 0.056 Uiso 1 1 calc R . .
C10 C 0.8854(8) 0.0705(5) 0.7519(5) 0.0442(19) Uani 1 1 d . . .
C11 C 0.7219(8) 0.2203(6) 0.7142(5) 0.052(2) Uani 1 1 d . . .
C12 C 0.8237(9) -0.0309(5) 0.7923(5) 0.050(2) Uani 1 1 d . . .
C13 C 0.7684(8) 0.1275(6) 0.6935(5) 0.048(2) Uani 1 1 d . . .
C14 C 0.7726(9) 0.2700(5) 0.8012(6) 0.057(2) Uani 1 1 d . . .
H14A H 0.7423 0.3362 0.8124 0.068 Uiso 1 1 calc R . .
C15 C 0.5902(9) -0.1479(7) 1.0852(5) 0.062(2) Uani 1 1 d . . .
H15A H 0.5051 -0.1272 1.1268 0.075 Uiso 1 1 calc R . .
C16 C 1.0391(9) 0.0569(6) 0.6850(5) 0.066(2) Uani 1 1 d . . .
H16A H 1.0153 0.0233 0.6263 0.099 Uiso 1 1 calc R . .
H16B H 1.1131 0.0178 0.7182 0.099 Uiso 1 1 calc R . .
H16C H 1.0840 0.1214 0.6692 0.099 Uiso 1 1 calc R . .
C17 C 0.9275(9) 0.1252(5) 0.8459(5) 0.050(2) Uani 1 1 d . . .
H17A H 1.0425 0.1297 0.8463 0.060 Uiso 1 1 calc R . .
C18 C 0.8577(9) 0.2268(6) 0.8639(5) 0.058(2) Uani 1 1 d . . .
H18A H 0.8757 0.2601 0.9213 0.069 Uiso 1 1 calc R . .
C19 C 0.6194(9) 0.2840(6) 0.6541(5) 0.068(2) Uani 1 1 d . . .
H19A H 0.5906 0.2465 0.5987 0.102 Uiso 1 1 calc R . .
H19B H 0.6766 0.3429 0.6324 0.102 Uiso 1 1 calc R . .
H19C H 0.5258 0.3033 0.6930 0.102 Uiso 1 1 calc R . .
C20 C 0.6385(11) -0.2463(7) 1.0856(5) 0.069(3) Uani 1 1 d . . .
H20A H 0.5862 -0.2917 1.1278 0.083 Uiso 1 1 calc R . .
C21 C 0.4893(10) 0.0481(7) 0.6267(6) 0.092(3) Uani 1 1 d . . .
H21A H 0.4403 0.0128 0.5762 0.137 Uiso 1 1 calc R . .
H21B H 0.4424 0.1132 0.6350 0.137 Uiso 1 1 calc R . .
H21C H 0.4742 0.0114 0.6866 0.137 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 C13 1.776(7) . ?
S1 C21 1.829(9) . ?
F1 C12 1.364(8) . ?
O2 C8 1.421(8) . ?
O2 C17 1.486(7) . ?
F2 C12 1.346(7) . ?
O1 C8 1.390(8) . ?
C5 C9 1.371(9) . ?
C5 C7 1.379(8) . ?
C5 C8 1.495(9) . ?
C6 C20 1.359(9) . ?
C6 C9 1.385(9) . ?
C7 C15 1.388(9) . ?
C8 C12 1.545(10) . ?
C10 C13 1.528(9) . ?
C10 C12 1.542(9) . ?
C10 C16 1.551(9) . ?
C10 C17 1.552(9) . ?
C11 C13 1.325(9) . ?
C11 C14 1.463(10) . ?
C11 C19 1.509(9) . ?
C14 C18 1.302(9) . ?
C15 C20 1.376(10) . ?
C17 C18 1.494(10) . ?

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
C13 S1 C21 102.7(4) . . ?
C8 O2 C17 106.4(5) . . ?
C9 C5 C7 119.1(6) . . ?
C9 C5 C8 118.5(6) . . ?
C7 C5 C8 122.4(6) . . ?
C20 C6 C9 119.2(7) . . ?
C5 C7 C15 119.8(7) . . ?
O1 C8 O2 112.4(6) . . ?
O1 C8 C5 113.6(6) . . ?
O2 C8 C5 110.4(5) . . ?
O1 C8 C12 105.3(5) . . ?
O2 C8 C12 100.1(5) . . ?
C5 C8 C12 114.3(6) . . ?
C5 C9 C6 121.4(7) . . ?
C13 C10 C12 114.2(6) . . ?
C13 C10 C16 107.3(5) . . ?
C12 C10 C16 111.1(6) . . ?
C13 C10 C17 113.9(6) . . ?
C12 C10 C17 101.9(5) . . ?
C16 C10 C17 108.3(6) . . ?
C13 C11 C14 120.0(7) . . ?
C13 C11 C19 125.8(7) . . ?
C14 C11 C19 114.2(7) . . ?
F2 C12 F1 106.8(6) . . ?
F2 C12 C10 114.1(5) . . ?
F1 C12 C10 109.7(6) . . ?
F2 C12 C8 112.8(6) . . ?
F1 C12 C8 107.8(6) . . ?
C10 C12 C8 105.6(6) . . ?
C11 C13 C10 123.2(7) . . ?
C11 C13 S1 121.6(6) . . ?
C10 C13 S1 115.1(5) . . ?
C18 C14 C11 123.6(7) . . ?
C20 C15 C7 120.0(7) . . ?
O2 C17 C18 107.2(5) . . ?
O2 C17 C10 105.4(5) . . ?
C18 C17 C10 116.9(6) . . ?
C14 C18 C17 121.7(7) . . ?
C6 C20 C15 120.5(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.82 2.05 2.848(6) 165.5 3_757

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        22.13
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.063


####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1973271'
loop_
_audit_author_name
_audit_author_address
'Xin Huang'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H29 Cl F4 O4 S2'
_chemical_formula_weight         665.13

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2309(5)
_cell_length_b                   13.2445(5)
_cell_length_c                   13.5012(6)
_cell_angle_alpha                66.7990(10)
_cell_angle_beta                 70.3300(10)
_cell_angle_gamma                75.6270(10)
_cell_volume                     1569.19(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9332
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .27
_exptl_crystal_size_min          .15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .903
_exptl_absorpt_correction_T_max  .954


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(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  'APEX-\/cò CCDC'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            32938
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.46
_reflns_number_total             7140
_reflns_number_gt                5151
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.0984P)²+0.4327P] 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         7140
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0754
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1818
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
S1 S 1.16931(8) -0.19898(5) 0.73300(6) 0.0674(2) Uani 1 1 d . . .
S2 S 1.61757(8) -0.71843(6) 1.01360(6) 0.0741(2) Uani 1 1 d . . .
Cl1 Cl 1.87095(9) -0.88489(8) 0.98786(8) 0.0999(3) Uani 1 1 d . . .
O2 O 1.35513(17) -0.53777(13) 0.83676(13) 0.0590(4) Uani 1 1 d . . .
F3 F 1.30915(19) -0.10181(11) 0.48813(14) 0.0792(4) Uani 1 1 d . . .
F1 F 1.08805(18) -0.61329(13) 0.86932(12) 0.0770(4) Uani 1 1 d . . .
F2 F 0.95631(15) -0.48545(14) 0.77329(16) 0.0855(5) Uani 1 1 d . . .
C6 C 1.2085(2) -0.40692(17) 0.72704(17) 0.0480(4) Uani 1 1 d . . .
C7 C 1.1874(2) -0.29834(17) 0.66927(18) 0.0506(5) Uani 1 1 d . . .
C8 C 1.1983(2) -0.49544(17) 0.68580(18) 0.0490(5) Uani 1 1 d . . .
H8A H 1.2844 -0.5484 0.6870 0.059 Uiso 1 1 calc R . .
F4 F 1.3076(2) -0.16347(15) 0.36223(13) 0.0924(5) Uani 1 1 d . . .
C10 C 1.1833(3) -0.44956(19) 0.5696(2) 0.0583(5) Uani 1 1 d . . .
H10A H 1.1793 -0.4991 0.5378 0.070 Uiso 1 1 calc R . .
O1 O 1.3552(3) -0.55184(19) 1.00795(17) 0.0908(7) Uani 1 1 d . . .
C12 C 1.1753(3) -0.3441(2) 0.5094(2) 0.0607(6) Uani 1 1 d . . .
H12A H 1.1673 -0.3242 0.4373 0.073 Uiso 1 1 calc R . .
C13 C 1.5290(3) -0.66171(19) 0.9120(2) 0.0581(5) Uani 1 1 d . . .
C14 C 1.5896(3) -0.7030(2) 0.8276(2) 0.0614(6) Uani 1 1 d . . .
H14A H 1.5556 -0.6817 0.7655 0.074 Uiso 1 1 calc R . .
C15 C 1.1782(3) -0.25239(18) 0.54801(19) 0.0569(5) Uani 1 1 d . . .
C16 C 1.2417(3) -0.44692(19) 0.83838(19) 0.0568(5) Uani 1 1 d . . .
H16A H 1.2700 -0.3877 0.8484 0.068 Uiso 1 1 calc R . .
H16B H 1.1602 -0.4721 0.8991 0.068 Uiso 1 1 calc R . .
C17 C 1.4056(3) -0.57949(19) 0.9266(2) 0.0596(6) Uani 1 1 d . . .
C18 C 1.0742(2) -0.5586(2) 0.7627(2) 0.0597(5) Uani 1 1 d . . .
O3 O 0.9491(2) -0.62182(19) 0.6852(2) 0.0944(7) Uani 1 1 d . . .
C20 C 1.4485(3) -0.2762(2) 0.4819(2) 0.0651(6) Uani 1 1 d . . .
C21 C 1.3109(3) -0.19762(19) 0.4712(2) 0.0644(6) Uani 1 1 d . . .
C22 C 1.5239(3) -0.2840(2) 0.5616(2) 0.0626(6) Uani 1 1 d . . .
C23 C 1.1491(3) -0.7471(2) 0.7246(2) 0.0629(6) Uani 1 1 d . . .
O4 O 1.4859(2) -0.33662(19) 0.42735(18) 0.0881(6) Uani 1 1 d . . .
C25 C 1.7085(3) -0.7811(2) 0.8425(2) 0.0690(6) Uani 1 1 d . . .
H25A H 1.7622 -0.8170 0.7921 0.083 Uiso 1 1 calc R . .
C26 C 1.0503(3) -0.6441(2) 0.7210(2) 0.0640(6) Uani 1 1 d . . .
C27 C 1.7344(3) -0.7971(2) 0.9388(2) 0.0650(6) Uani 1 1 d . . .
C28 C 1.0474(3) -0.1659(2) 0.5324(3) 0.0802(8) Uani 1 1 d . . .
H28A H 0.9646 -0.1994 0.5798 0.120 Uiso 1 1 calc R . .
H28B H 1.0451 -0.1400 0.4557 0.120 Uiso 1 1 calc R . .
H28C H 1.0512 -0.1046 0.5519 0.120 Uiso 1 1 calc R . .
C29 C 1.2558(3) -0.7831(2) 0.7769(2) 0.0748(7) Uani 1 1 d . . .
H29A H 1.2717 -0.7401 0.8109 0.090 Uiso 1 1 calc R . .
C31 C 1.5916(3) -0.3880(3) 0.6105(3) 0.0834(8) Uani 1 1 d . . .
H31A H 1.5863 -0.4483 0.5937 0.100 Uiso 1 1 calc R . .
C37 C 1.0128(4) -0.2309(3) 0.8467(3) 0.0944(10) Uani 1 1 d . . .
H37A H 0.9844 -0.2973 0.8506 0.113 Uiso 1 1 calc R . .
H37B H 1.0330 -0.2456 0.9167 0.113 Uiso 1 1 calc R . .
C39 C 1.1303(4) -0.8112(3) 0.6712(3) 0.0903(9) Uani 1 1 d . . .
H39A H 1.0606 -0.7868 0.6339 0.108 Uiso 1 1 calc R . .
C53 C 1.5357(3) -0.1950(3) 0.5864(3) 0.0845(8) Uani 1 1 d . . .
H53A H 1.4917 -0.1246 0.5541 0.101 Uiso 1 1 calc R . .
C54 C 1.6779(4) -0.3144(4) 0.7080(3) 0.1019(11) Uani 1 1 d . . .
H54A H 1.7291 -0.3242 0.7572 0.122 Uiso 1 1 calc R . .
C50 C 1.3382(4) -0.8826(3) 0.7784(3) 0.0998(11) Uani 1 1 d . . .
H50A H 1.4095 -0.9074 0.8141 0.120 Uiso 1 1 calc R . .
C55 C 1.6671(4) -0.4019(4) 0.6845(4) 0.1058(12) Uani 1 1 d . . .
H55A H 1.7107 -0.4720 0.7181 0.127 Uiso 1 1 calc R . .
C56 C 1.6127(4) -0.2111(4) 0.6590(3) 0.1052(12) Uani 1 1 d . . .
H56A H 1.6207 -0.1510 0.6751 0.126 Uiso 1 1 calc R . .
C51 C 1.2133(5) -0.9093(3) 0.6731(4) 0.1159(14) Uani 1 1 d . . .
H51A H 1.1999 -0.9515 0.6370 0.139 Uiso 1 1 calc R . .
C52 C 1.3150(5) -0.9459(3) 0.7270(4) 0.1124(14) Uani 1 1 d . . .
H52A H 1.3696 -1.0140 0.7294 0.135 Uiso 1 1 calc R . .
C59 C 0.6459(5) -0.0730(4) 0.8973(5) 0.1419(18) Uani 1 1 d . . .
H59A H 0.5644 -0.0964 0.9572 0.213 Uiso 1 1 calc R . .
H59B H 0.6285 -0.0589 0.8272 0.213 Uiso 1 1 calc R . .
H59C H 0.6667 -0.0065 0.8980 0.213 Uiso 1 1 calc R . .
C58 C 0.7625(5) -0.1584(5) 0.9117(5) 0.1490(19) Uani 1 1 d . . .
H58A H 0.7745 -0.1748 0.9850 0.179 Uiso 1 1 calc R . .
H58B H 0.7391 -0.2249 0.9114 0.179 Uiso 1 1 calc R . .
C57 C 0.8924(5) -0.1355(4) 0.8315(4) 0.1343(16) Uani 1 1 d . . .
H57A H 0.9188 -0.0714 0.8343 0.161 Uiso 1 1 calc R . .
H57B H 0.8800 -0.1160 0.7577 0.161 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 C7 1.781(2) . ?
S1 C37 1.808(4) . ?
S2 C27 1.712(3) . ?
S2 C13 1.719(2) . ?
Cl1 C27 1.718(3) . ?
O2 C17 1.340(3) . ?
O2 C16 1.451(3) . ?
F3 C21 1.370(3) . ?
F1 C18 1.372(3) . ?
F2 C18 1.351(3) . ?
C6 C7 1.341(3) . ?
C6 C16 1.511(3) . ?
C6 C8 1.520(3) . ?
C7 C15 1.533(3) . ?
C8 C10 1.489(3) . ?
C8 C18 1.532(3) . ?
C8 H8A 0.9800 . ?
F4 C21 1.369(3) . ?
C10 C12 1.309(3) . ?
C10 H10A 0.9300 . ?
O1 C17 1.203(3) . ?
C12 C15 1.508(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.352(3) . ?
C13 C17 1.462(3) . ?
C14 C25 1.402(4) . ?
C14 H14A 0.9300 . ?
C15 C28 1.545(3) . ?
C15 C21 1.547(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C26 1.546(3) . ?
O3 C26 1.210(3) . ?
C20 O4 1.205(3) . ?
C20 C22 1.482(4) . ?
C20 C21 1.542(4) . ?
C22 C53 1.388(4) . ?
C22 C31 1.389(4) . ?
C23 C29 1.382(4) . ?
C23 C39 1.391(4) . ?
C23 C26 1.477(4) . ?
C25 C27 1.340(4) . ?
C25 H25A 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C50 1.373(4) . ?
C29 H29A 0.9300 . ?
C31 C55 1.391(5) . ?
C31 H31A 0.9300 . ?
C37 C57 1.533(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C39 C51 1.360(5) . ?
C39 H39A 0.9300 . ?
C53 C56 1.378(4) . ?
C53 H53A 0.9300 . ?
C54 C55 1.355(6) . ?
C54 C56 1.373(5) . ?
C54 H54A 0.9300 . ?
C50 C52 1.383(6) . ?
C50 H50A 0.9300 . ?
C55 H55A 0.9300 . ?
C56 H56A 0.9300 . ?
C51 C52 1.352(6) . ?
C51 H51A 0.9300 . ?
C52 H52A 0.9300 . ?
C59 C58 1.433(6) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C58 C57 1.416(7) . ?
C58 H58A 0.9700 . ?
C58 H58B 0.9700 . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?

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
C7 S1 C37 101.65(13) . . ?
C27 S2 C13 90.05(12) . . ?
C17 O2 C16 115.06(17) . . ?
C7 C6 C16 120.95(18) . . ?
C7 C6 C8 122.37(18) . . ?
C16 C6 C8 116.68(18) . . ?
C6 C7 C15 123.52(19) . . ?
C6 C7 S1 120.00(17) . . ?
C15 C7 S1 116.47(15) . . ?
C10 C8 C6 112.91(17) . . ?
C10 C8 C18 108.33(18) . . ?
C6 C8 C18 110.95(18) . . ?
C10 C8 H8A 108.2 . . ?
C6 C8 H8A 108.2 . . ?
C18 C8 H8A 108.2 . . ?
C12 C10 C8 124.3(2) . . ?
C12 C10 H10A 117.8 . . ?
C8 C10 H10A 117.8 . . ?
C10 C12 C15 125.0(2) . . ?
C10 C12 H12A 117.5 . . ?
C15 C12 H12A 117.5 . . ?
C14 C13 C17 130.0(2) . . ?
C14 C13 S2 111.40(19) . . ?
C17 C13 S2 118.59(18) . . ?
C13 C14 C25 113.8(2) . . ?
C13 C14 H14A 123.1 . . ?
C25 C14 H14A 123.1 . . ?
C12 C15 C7 111.09(18) . . ?
C12 C15 C28 108.6(2) . . ?
C7 C15 C28 112.2(2) . . ?
C12 C15 C21 106.9(2) . . ?
C7 C15 C21 108.88(18) . . ?
C28 C15 C21 109.0(2) . . ?
O2 C16 C6 106.46(17) . . ?
O2 C16 H16A 110.4 . . ?
C6 C16 H16A 110.4 . . ?
O2 C16 H16B 110.4 . . ?
C6 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
O1 C17 O2 123.9(2) . . ?
O1 C17 C13 125.1(2) . . ?
O2 C17 C13 111.1(2) . . ?
F2 C18 F1 105.1(2) . . ?
F2 C18 C8 109.23(19) . . ?
F1 C18 C8 111.84(19) . . ?
F2 C18 C26 108.56(19) . . ?
F1 C18 C26 107.77(19) . . ?
C8 C18 C26 113.9(2) . . ?
O4 C20 C22 121.7(3) . . ?
O4 C20 C21 116.0(3) . . ?
C22 C20 C21 122.1(2) . . ?
F4 C21 F3 104.28(18) . . ?
F4 C21 C20 107.5(2) . . ?
F3 C21 C20 111.6(2) . . ?
F4 C21 C15 109.0(2) . . ?
F3 C21 C15 110.5(2) . . ?
C20 C21 C15 113.49(19) . . ?
C53 C22 C31 118.8(3) . . ?
C53 C22 C20 124.7(2) . . ?
C31 C22 C20 116.5(3) . . ?
C29 C23 C39 119.0(3) . . ?
C29 C23 C26 124.9(2) . . ?
C39 C23 C26 116.1(3) . . ?
C27 C25 C14 111.0(2) . . ?
C27 C25 H25A 124.5 . . ?
C14 C25 H25A 124.5 . . ?
O3 C26 C23 122.7(2) . . ?
O3 C26 C18 117.0(2) . . ?
C23 C26 C18 120.3(2) . . ?
C25 C27 S2 113.8(2) . . ?
C25 C27 Cl1 125.8(2) . . ?
S2 C27 Cl1 120.41(16) . . ?
C15 C28 H28A 109.5 . . ?
C15 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C15 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C50 C29 C23 119.8(3) . . ?
C50 C29 H29A 120.1 . . ?
C23 C29 H29A 120.1 . . ?
C22 C31 C55 120.0(3) . . ?
C22 C31 H31A 120.0 . . ?
C55 C31 H31A 120.0 . . ?
C57 C37 S1 111.7(3) . . ?
C57 C37 H37A 109.3 . . ?
S1 C37 H37A 109.3 . . ?
C57 C37 H37B 109.3 . . ?
S1 C37 H37B 109.3 . . ?
H37A C37 H37B 107.9 . . ?
C51 C39 C23 120.4(4) . . ?
C51 C39 H39A 119.8 . . ?
C23 C39 H39A 119.8 . . ?
C56 C53 C22 119.9(3) . . ?
C56 C53 H53A 120.1 . . ?
C22 C53 H53A 120.1 . . ?
C55 C54 C56 119.7(3) . . ?
C55 C54 H54A 120.1 . . ?
C56 C54 H54A 120.1 . . ?
C29 C50 C52 119.9(4) . . ?
C29 C50 H50A 120.0 . . ?
C52 C50 H50A 120.0 . . ?
C54 C55 C31 120.6(3) . . ?
C54 C55 H55A 119.7 . . ?
C31 C55 H55A 119.7 . . ?
C54 C56 C53 121.0(4) . . ?
C54 C56 H56A 119.5 . . ?
C53 C56 H56A 119.5 . . ?
C52 C51 C39 120.5(4) . . ?
C52 C51 H51A 119.7 . . ?
C39 C51 H51A 119.7 . . ?
C51 C52 C50 120.3(3) . . ?
C51 C52 H52A 119.9 . . ?
C50 C52 H52A 119.9 . . ?
C58 C59 H59A 109.5 . . ?
C58 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C58 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C58 C59 116.5(5) . . ?
C57 C58 H58A 108.2 . . ?
C59 C58 H58A 108.2 . . ?
C57 C58 H58B 108.2 . . ?
C59 C58 H58B 108.2 . . ?
H58A C58 H58B 107.3 . . ?
C58 C57 C37 114.9(4) . . ?
C58 C57 H57A 108.5 . . ?
C37 C57 H57A 108.5 . . ?
C58 C57 H57B 108.5 . . ?
C37 C57 H57B 108.5 . . ?
H57A C57 H57B 107.5 . . ?

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
C16 C6 C7 C15 169.2(2) . . . . ?
C8 C6 C7 C15 -11.7(3) . . . . ?
C16 C6 C7 S1 -10.5(3) . . . . ?
C8 C6 C7 S1 168.57(16) . . . . ?
C37 S1 C7 C6 -62.6(2) . . . . ?
C37 S1 C7 C15 117.6(2) . . . . ?
C7 C6 C8 C10 8.2(3) . . . . ?
C16 C6 C8 C10 -172.8(2) . . . . ?
C7 C6 C8 C18 -113.7(2) . . . . ?
C16 C6 C8 C18 65.4(2) . . . . ?
C6 C8 C10 C12 -1.9(3) . . . . ?
C18 C8 C10 C12 121.4(3) . . . . ?
C8 C10 C12 C15 -0.8(4) . . . . ?
C27 S2 C13 C14 -0.1(2) . . . . ?
C27 S2 C13 C17 -179.9(2) . . . . ?
C17 C13 C14 C25 179.7(2) . . . . ?
S2 C13 C14 C25 0.0(3) . . . . ?
C10 C12 C15 C7 -1.7(4) . . . . ?
C10 C12 C15 C28 -125.5(3) . . . . ?
C10 C12 C15 C21 117.0(3) . . . . ?
C6 C7 C15 C12 8.0(3) . . . . ?
S1 C7 C15 C12 -172.25(16) . . . . ?
C6 C7 C15 C28 129.8(2) . . . . ?
S1 C7 C15 C28 -50.4(3) . . . . ?
C6 C7 C15 C21 -109.4(2) . . . . ?
S1 C7 C15 C21 70.3(2) . . . . ?
C17 O2 C16 C6 175.71(19) . . . . ?
C7 C6 C16 O2 -135.8(2) . . . . ?
C8 C6 C16 O2 45.1(3) . . . . ?
C16 O2 C17 O1 6.0(4) . . . . ?
C16 O2 C17 C13 -173.68(19) . . . . ?
C14 C13 C17 O1 176.1(3) . . . . ?
S2 C13 C17 O1 -4.3(4) . . . . ?
C14 C13 C17 O2 -4.2(4) . . . . ?
S2 C13 C17 O2 175.46(16) . . . . ?
C10 C8 C18 F2 -70.4(2) . . . . ?
C6 C8 C18 F2 54.0(2) . . . . ?
C10 C8 C18 F1 173.59(18) . . . . ?
C6 C8 C18 F1 -61.9(2) . . . . ?
C10 C8 C18 C26 51.1(3) . . . . ?
C6 C8 C18 C26 175.57(19) . . . . ?
O4 C20 C21 F4 -37.2(3) . . . . ?
C22 C20 C21 F4 147.9(2) . . . . ?
O4 C20 C21 F3 -150.9(2) . . . . ?
C22 C20 C21 F3 34.1(3) . . . . ?
O4 C20 C21 C15 83.4(3) . . . . ?
C22 C20 C21 C15 -91.5(3) . . . . ?
C12 C15 C21 F4 55.7(2) . . . . ?
C7 C15 C21 F4 175.79(18) . . . . ?
C28 C15 C21 F4 -61.5(3) . . . . ?
C12 C15 C21 F3 169.74(18) . . . . ?
C7 C15 C21 F3 -70.2(2) . . . . ?
C28 C15 C21 F3 52.5(3) . . . . ?
C12 C15 C21 C20 -64.0(2) . . . . ?
C7 C15 C21 C20 56.1(3) . . . . ?
C28 C15 C21 C20 178.8(2) . . . . ?
O4 C20 C22 C53 147.8(3) . . . . ?
C21 C20 C22 C53 -37.6(4) . . . . ?
O4 C20 C22 C31 -29.4(4) . . . . ?
C21 C20 C22 C31 145.2(2) . . . . ?
C13 C14 C25 C27 0.3(3) . . . . ?
C29 C23 C26 O3 -171.6(3) . . . . ?
C39 C23 C26 O3 8.1(4) . . . . ?
C29 C23 C26 C18 9.1(4) . . . . ?
C39 C23 C26 C18 -171.3(3) . . . . ?
F2 C18 C26 O3 13.7(3) . . . . ?
F1 C18 C26 O3 127.1(3) . . . . ?
C8 C18 C26 O3 -108.2(3) . . . . ?
F2 C18 C26 C23 -166.9(2) . . . . ?
F1 C18 C26 C23 -53.6(3) . . . . ?
C8 C18 C26 C23 71.1(3) . . . . ?
C14 C25 C27 S2 -0.4(3) . . . . ?
C14 C25 C27 Cl1 -179.4(2) . . . . ?
C13 S2 C27 C25 0.3(2) . . . . ?
C13 S2 C27 Cl1 179.37(17) . . . . ?
C39 C23 C29 C50 -2.1(4) . . . . ?
C26 C23 C29 C50 177.5(3) . . . . ?
C53 C22 C31 C55 1.3(5) . . . . ?
C20 C22 C31 C55 178.7(3) . . . . ?
C7 S1 C37 C57 -114.4(3) . . . . ?
C29 C23 C39 C51 1.8(5) . . . . ?
C26 C23 C39 C51 -177.9(3) . . . . ?
C31 C22 C53 C56 -0.5(5) . . . . ?
C20 C22 C53 C56 -177.7(3) . . . . ?
C23 C29 C50 C52 0.6(5) . . . . ?
C56 C54 C55 C31 0.5(6) . . . . ?
C22 C31 C55 C54 -1.3(5) . . . . ?
C55 C54 C56 C53 0.3(6) . . . . ?
C22 C53 C56 C54 -0.3(6) . . . . ?
C23 C39 C51 C52 0.1(6) . . . . ?
C39 C51 C52 C50 -1.6(7) . . . . ?
C29 C50 C52 C51 1.3(6) . . . . ?
C59 C58 C57 C37 -177.3(5) . . . . ?
S1 C37 C57 C58 174.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062



