# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 1502489'
_audit_update_record             
;
2016-09-04 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Br1 Cl2 O1 S1'
_chemical_formula_weight         454.21

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'
Cl Cl 0.1484 0.1585 '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)/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                   5.0603(8)
_cell_length_b                   21.361(4)
_cell_length_c                   17.169(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.419(4)
_cell_angle_gamma                90.00
_cell_volume                     1844.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9208
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.60

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      1.636
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228
_exptl_absorpt_coefficient_mu    2.638
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            15719
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4290
_reflns_number_gt                3876
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker 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)+(0.0298P)²+0.7647P] 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         4290
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_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 0.44272(4) 0.270516(9) 0.527971(10) 0.02005(7) Uani 1 1 d . . .
C1 C 0.4109(4) 0.45218(10) 0.14067(11) 0.0259(4) Uani 1 1 d . . .
C2 C 0.6187(5) 0.42554(11) 0.10641(12) 0.0291(5) Uani 1 1 d . . .
C3 C 0.3030(4) 0.42288(10) 0.20168(11) 0.0231(4) Uani 1 1 d . . .
C4 C 0.7182(4) 0.36855(10) 0.13353(11) 0.0218(4) Uani 1 1 d . . .
C5 C 0.4042(4) 0.36540(9) 0.22867(11) 0.0183(4) Uani 1 1 d . . .
C6 C 0.6128(4) 0.33771(9) 0.19489(10) 0.0159(3) Uani 1 1 d . . .
C7 C -0.0525(4) 0.01162(9) 0.11680(10) 0.0176(4) Uani 1 1 d . . .
C8 C -0.1457(4) 0.07070(10) 0.09548(11) 0.0203(4) Uani 1 1 d . . .
C9 C 0.1779(4) 0.00331(10) 0.16785(11) 0.0198(4) Uani 1 1 d . . .
C10 C -0.0062(4) 0.12313(9) 0.12524(11) 0.0190(4) Uani 1 1 d . . .
C11 C 0.3176(4) 0.05564(10) 0.19720(11) 0.0200(4) Uani 1 1 d . . .
C12 C 0.2252(4) 0.11496(9) 0.17577(10) 0.0166(4) Uani 1 1 d . . .
C13 C 0.0816(5) 0.15938(11) 0.46247(12) 0.0258(4) Uani 1 1 d . . .
C14 C 0.7728(4) 0.31591(10) 0.39646(11) 0.0195(4) Uani 1 1 d . . .
C15 C 0.4253(4) 0.23678(9) 0.42453(10) 0.0149(3) Uani 1 1 d . . .
C16 C 0.2509(4) 0.18728(9) 0.40526(10) 0.0163(3) Uani 1 1 d . . .
C17 C 0.5872(3) 0.26271(9) 0.37236(10) 0.0150(4) Uani 1 1 d . . .
C18 C 0.2361(4) 0.16313(9) 0.32917(10) 0.0167(4) Uani 1 1 d . . .
C19 C 0.5667(3) 0.23759(8) 0.29595(10) 0.0135(3) Uani 1 1 d . . .
C20 C 0.3904(4) 0.18805(9) 0.27532(10) 0.0151(3) Uani 1 1 d . . .
Cl1 Cl 0.27993(15) 0.52398(3) 0.10652(3) 0.04487(17) Uani 1 1 d . . .
Cl2 Cl -0.22713(10) -0.05421(2) 0.07879(3) 0.02583(11) Uani 1 1 d . . .
O1 O 0.3756(3) 0.16785(7) 0.19853(7) 0.0205(3) Uani 1 1 d . . .
S1 S 0.76583(9) 0.26590(2) 0.22492(3) 0.01592(10) Uani 1 1 d . . .
H9 H 0.122(4) 0.1307(11) 0.3146(12) 0.011(5) Uiso 1 1 d . . .
H6 H 0.236(4) -0.0386(12) 0.1825(13) 0.021(6) Uiso 1 1 d . . .
H5 H -0.293(5) 0.0767(12) 0.0639(14) 0.027(6) Uiso 1 1 d . . .
H4 H 0.328(4) 0.3467(11) 0.2690(13) 0.021(6) Uiso 1 1 d . . .
H13 H 0.886(5) 0.3081(12) 0.4450(14) 0.028(6) Uiso 1 1 d . . .
H2 H 0.156(5) 0.4410(13) 0.2254(14) 0.033(7) Uiso 1 1 d . . .
H14 H 0.677(5) 0.3516(13) 0.4074(14) 0.028(6) Uiso 1 1 d . . .
H15 H 0.885(5) 0.3233(12) 0.3562(14) 0.030(6) Uiso 1 1 d . . .
H3 H 0.863(5) 0.3495(13) 0.1119(14) 0.031(7) Uiso 1 1 d . . .
H8 H 0.488(5) 0.0488(14) 0.2321(15) 0.042(7) Uiso 1 1 d . . .
H1 H 0.700(5) 0.4448(14) 0.0671(17) 0.044(8) Uiso 1 1 d . . .
H7 H -0.061(4) 0.1643(12) 0.1098(13) 0.022(6) Uiso 1 1 d . . .
H10 H -0.017(6) 0.1945(17) 0.4855(18) 0.058(9) Uiso 1 1 d . . .
H11 H 0.181(6) 0.1376(15) 0.5021(18) 0.050(8) Uiso 1 1 d . . .
H12 H -0.034(6) 0.1348(17) 0.4390(19) 0.059(10) Uiso 1 1 d . . .


_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 C15 1.9095(17) . ?
C1 C2 1.383(3) . ?
C1 C3 1.384(3) . ?
C1 Cl1 1.746(2) . ?
C2 C4 1.378(3) . ?
C2 H1 0.93(3) . ?
C3 C5 1.390(3) . ?
C3 H2 0.97(3) . ?
C4 C6 1.398(3) . ?
C4 H3 0.95(3) . ?
C5 C6 1.392(3) . ?
C5 H4 0.92(2) . ?
C6 S1 1.7690(19) . ?
C7 C8 1.382(3) . ?
C7 C9 1.390(3) . ?
C7 Cl2 1.7477(19) . ?
C8 C10 1.390(3) . ?
C8 H5 0.88(2) . ?
C9 C11 1.387(3) . ?
C9 H6 0.97(2) . ?
C10 C12 1.388(3) . ?
C10 H7 0.95(2) . ?
C11 C12 1.386(3) . ?
C11 H8 1.00(3) . ?
C12 O1 1.394(2) . ?
C13 C16 1.497(3) . ?
C13 H10 1.01(4) . ?
C13 H11 0.93(3) . ?
C13 H12 0.85(3) . ?
C14 C17 1.503(3) . ?
C14 H13 0.97(2) . ?
C14 H14 0.93(3) . ?
C14 H15 0.96(2) . ?
C15 C16 1.393(3) . ?
C15 C17 1.394(2) . ?
C16 C18 1.399(2) . ?
C17 C19 1.410(2) . ?
C18 C20 1.382(2) . ?
C18 H9 0.92(2) . ?
C19 C20 1.404(3) . ?
C19 S1 1.7728(17) . ?
C20 O1 1.381(2) . ?

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
C2 C1 C3 121.3(2) . . ?
C2 C1 Cl1 119.77(16) . . ?
C3 C1 Cl1 118.98(17) . . ?
C4 C2 C1 119.06(19) . . ?
C4 C2 H1 117.5(18) . . ?
C1 C2 H1 123.3(18) . . ?
C1 C3 C5 119.35(19) . . ?
C1 C3 H2 121.7(15) . . ?
C5 C3 H2 119.0(15) . . ?
C2 C4 C6 121.01(19) . . ?
C2 C4 H3 121.0(16) . . ?
C6 C4 H3 117.9(16) . . ?
C3 C5 C6 120.32(18) . . ?
C3 C5 H4 117.8(15) . . ?
C6 C5 H4 121.9(15) . . ?
C5 C6 C4 119.00(18) . . ?
C5 C6 S1 125.08(14) . . ?
C4 C6 S1 115.91(15) . . ?
C8 C7 C9 121.40(18) . . ?
C8 C7 Cl2 119.50(14) . . ?
C9 C7 Cl2 119.10(15) . . ?
C7 C8 C10 119.59(18) . . ?
C7 C8 H5 122.4(17) . . ?
C10 C8 H5 118.0(17) . . ?
C11 C9 C7 118.95(18) . . ?
C11 C9 H6 121.7(14) . . ?
C7 C9 H6 119.3(14) . . ?
C12 C10 C8 119.12(18) . . ?
C12 C10 H7 119.4(14) . . ?
C8 C10 H7 121.4(14) . . ?
C12 C11 C9 119.81(17) . . ?
C12 C11 H8 122.2(17) . . ?
C9 C11 H8 118.0(17) . . ?
C11 C12 C10 121.13(18) . . ?
C11 C12 O1 120.60(17) . . ?
C10 C12 O1 118.00(17) . . ?
C16 C13 H10 107.8(19) . . ?
C16 C13 H11 112.3(18) . . ?
H10 C13 H11 110(3) . . ?
C16 C13 H12 110(2) . . ?
H10 C13 H12 107(3) . . ?
H11 C13 H12 109(3) . . ?
C17 C14 H13 113.4(15) . . ?
C17 C14 H14 110.5(15) . . ?
H13 C14 H14 104(2) . . ?
C17 C14 H15 109.2(15) . . ?
H13 C14 H15 108(2) . . ?
H14 C14 H15 112(2) . . ?
C16 C15 C17 123.44(16) . . ?
C16 C15 Br1 118.00(13) . . ?
C17 C15 Br1 118.56(14) . . ?
C15 C16 C18 117.90(16) . . ?
C15 C16 C13 122.69(17) . . ?
C18 C16 C13 119.41(17) . . ?
C15 C17 C19 117.32(16) . . ?
C15 C17 C14 121.18(16) . . ?
C19 C17 C14 121.50(16) . . ?
C20 C18 C16 120.50(17) . . ?
C20 C18 H9 119.6(13) . . ?
C16 C18 H9 119.9(13) . . ?
C20 C19 C17 120.00(16) . . ?
C20 C19 S1 118.52(13) . . ?
C17 C19 S1 121.46(14) . . ?
O1 C20 C18 122.95(17) . . ?
O1 C20 C19 116.20(15) . . ?
C18 C20 C19 120.82(16) . . ?
C20 O1 C12 119.38(14) . . ?
C6 S1 C19 103.43(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C4 0.4(3) . . . . ?
Cl1 C1 C2 C4 -179.37(16) . . . . ?
C2 C1 C3 C5 -0.4(3) . . . . ?
Cl1 C1 C3 C5 179.31(15) . . . . ?
C1 C2 C4 C6 -0.2(3) . . . . ?
C1 C3 C5 C6 0.3(3) . . . . ?
C3 C5 C6 C4 -0.1(3) . . . . ?
C3 C5 C6 S1 178.35(15) . . . . ?
C2 C4 C6 C5 0.0(3) . . . . ?
C2 C4 C6 S1 -178.55(16) . . . . ?
C9 C7 C8 C10 0.3(3) . . . . ?
Cl2 C7 C8 C10 -179.58(14) . . . . ?
C8 C7 C9 C11 -0.6(3) . . . . ?
Cl2 C7 C9 C11 179.26(14) . . . . ?
C7 C8 C10 C12 0.2(3) . . . . ?
C7 C9 C11 C12 0.4(3) . . . . ?
C9 C11 C12 C10 0.1(3) . . . . ?
C9 C11 C12 O1 -173.81(16) . . . . ?
C8 C10 C12 C11 -0.4(3) . . . . ?
C8 C10 C12 O1 173.65(16) . . . . ?
C17 C15 C16 C18 -0.9(3) . . . . ?
Br1 C15 C16 C18 179.26(13) . . . . ?
C17 C15 C16 C13 179.01(19) . . . . ?
Br1 C15 C16 C13 -0.9(3) . . . . ?
C16 C15 C17 C19 1.2(3) . . . . ?
Br1 C15 C17 C19 -178.92(13) . . . . ?
C16 C15 C17 C14 -179.68(17) . . . . ?
Br1 C15 C17 C14 0.2(2) . . . . ?
C15 C16 C18 C20 -0.1(3) . . . . ?
C13 C16 C18 C20 -179.96(19) . . . . ?
C15 C17 C19 C20 -0.6(3) . . . . ?
C14 C17 C19 C20 -179.73(17) . . . . ?
C15 C17 C19 S1 -179.05(13) . . . . ?
C14 C17 C19 S1 1.8(2) . . . . ?
C16 C18 C20 O1 -177.16(17) . . . . ?
C16 C18 C20 C19 0.6(3) . . . . ?
C17 C19 C20 O1 177.67(15) . . . . ?
S1 C19 C20 O1 -3.8(2) . . . . ?
C17 C19 C20 C18 -0.3(3) . . . . ?
S1 C19 C20 C18 178.21(14) . . . . ?
C18 C20 O1 C12 -8.4(3) . . . . ?
C19 C20 O1 C12 173.68(16) . . . . ?
C11 C12 O1 C20 -74.7(2) . . . . ?
C10 C12 O1 C20 111.24(19) . . . . ?
C5 C6 S1 C19 6.35(18) . . . . ?
C4 C6 S1 C19 -175.15(15) . . . . ?
C20 C19 S1 C6 105.20(15) . . . . ?
C17 C19 S1 C6 -76.34(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_cai2
_database_code_depnum_ccdc_archive 'CCDC 1502490'
_audit_update_record             
;
2016-09-04 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Cl1 N1 O3 S1'
_chemical_formula_weight         433.89

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'
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           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                   18.742(2)
_cell_length_b                   15.6215(19)
_cell_length_c                   13.9700(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.216(4)
_cell_angle_gamma                90.00
_cell_volume                     4048.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8351
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      1.424
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            34730
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.62
_reflns_number_total             9336
_reflns_number_gt                6172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker 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)+(0.0487P)²+4.4235P] 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         9335
_refine_ls_number_parameters     554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.058
_refine_ls_shift/su_mean         0.001

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
C48 C 0.54111(19) 0.4280(2) -0.2345(3) 0.0551(9) Uani 1 1 d . . .
H48A H 0.5360 0.4707 -0.2845 0.083 Uiso 1 1 calc R . .
H48B H 0.4969 0.4236 -0.2076 0.083 Uiso 1 1 calc R . .
H48C H 0.5520 0.3738 -0.2612 0.083 Uiso 1 1 calc R . .
H101 H 0.350(3) 0.511(5) 0.690(5) 0.16(3) Uiso 1 1 d . . .
H102 H 0.383(3) 0.465(3) 0.630(4) 0.11(2) Uiso 1 1 d . . .
H100 H 0.333(3) 0.419(4) 0.672(4) 0.108(18) Uiso 1 1 d . . .
C1 C -0.20021(17) 0.7816(2) 0.3216(2) 0.0374(7) Uani 1 1 d . . .
C2 C -0.12944(15) 0.74596(18) 0.31864(19) 0.0306(6) Uani 1 1 d . . .
C3 C -0.07189(15) 0.79748(17) 0.31116(18) 0.0288(6) Uani 1 1 d . . .
H3 H -0.0781 0.8565 0.3085 0.035 Uiso 1 1 calc R . .
C4 C -0.00305(14) 0.76238(16) 0.30748(17) 0.0246(5) Uani 1 1 d . . .
C5 C 0.00761(14) 0.67176(16) 0.31310(17) 0.0242(5) Uani 1 1 d . . .
C6 C -0.05411(15) 0.62053(18) 0.3205(2) 0.0319(6) Uani 1 1 d . . .
H6 H -0.0492 0.5613 0.3239 0.038 Uiso 1 1 calc R . .
C7 C -0.12021(15) 0.65615(19) 0.3227(2) 0.0341(6) Uani 1 1 d . . .
H7 H -0.1597 0.6210 0.3270 0.041 Uiso 1 1 calc R . .
C8 C 0.05543(14) 0.81700(17) 0.29790(18) 0.0278(6) Uani 1 1 d . . .
H8 H 0.0479 0.8758 0.2952 0.033 Uiso 1 1 calc R . .
C9 C 0.12223(14) 0.78613(17) 0.29251(19) 0.0286(6) Uani 1 1 d . . .
H9 H 0.1600 0.8233 0.2860 0.034 Uiso 1 1 calc R . .
C10 C 0.13381(14) 0.69699(17) 0.29680(18) 0.0269(6) Uani 1 1 d . . .
C11 C 0.07899(14) 0.64047(16) 0.30911(18) 0.0254(6) Uani 1 1 d . . .
C12 C 0.26005(14) 0.71614(17) 0.3012(2) 0.0324(6) Uani 1 1 d . . .
C13 C 0.29252(16) 0.73567(19) 0.3924(2) 0.0379(7) Uani 1 1 d . . .
H13 H 0.2730 0.7164 0.4460 0.045 Uiso 1 1 calc R . .
C14 C 0.35472(16) 0.7843(2) 0.4042(2) 0.0405(7) Uani 1 1 d . . .
H14 H 0.3776 0.7979 0.4658 0.049 Uiso 1 1 calc R . .
C15 C 0.28837(17) 0.7436(2) 0.2201(2) 0.0417(7) Uani 1 1 d . . .
H15 H 0.2660 0.7292 0.1585 0.050 Uiso 1 1 calc R . .
C16 C 0.35010(16) 0.7925(2) 0.2322(2) 0.0425(8) Uani 1 1 d . . .
H16 H 0.3697 0.8118 0.1787 0.051 Uiso 1 1 calc R . .
C17 C 0.38237(15) 0.81242(19) 0.3238(2) 0.0367(7) Uani 1 1 d . . .
C18 C 0.3416(2) 0.4713(3) 0.6493(3) 0.0557(10) Uani 1 1 d . . .
C19 C 0.28400(17) 0.49168(18) 0.5653(2) 0.0386(7) Uani 1 1 d . . .
C20 C 0.29447(16) 0.47407(19) 0.4705(2) 0.0405(7) Uani 1 1 d . . .
H20 H 0.3385 0.4521 0.4585 0.049 Uiso 1 1 calc R . .
C21 C 0.24040(15) 0.48876(18) 0.3937(2) 0.0363(7) Uani 1 1 d . . .
H21 H 0.2478 0.4766 0.3307 0.044 Uiso 1 1 calc R . .
C22 C 0.17524(15) 0.52184(16) 0.41216(19) 0.0288(6) Uani 1 1 d . . .
C23 C 0.16361(17) 0.54056(18) 0.5053(2) 0.0358(7) Uani 1 1 d . . .
H23 H 0.1195 0.5625 0.5170 0.043 Uiso 1 1 calc R . .
C24 C 0.21847(17) 0.52623(19) 0.5811(2) 0.0408(7) Uani 1 1 d . . .
H24 H 0.2113 0.5400 0.6437 0.049 Uiso 1 1 calc R . .
C25 C 0.90468(14) 0.73022(17) 0.06444(17) 0.0256(6) Uani 1 1 d . . .
C26 C 0.81718(14) 0.61582(16) 0.07675(19) 0.0272(6) Uani 1 1 d . . .
C27 C 0.97510(14) 0.75902(18) 0.05739(18) 0.0293(6) Uani 1 1 d . . .
H27 H 0.9842 0.8174 0.0538 0.035 Uiso 1 1 calc R . .
C28 C 0.88998(14) 0.64079(17) 0.06944(18) 0.0265(6) Uani 1 1 d . . .
C29 C 0.78125(15) 0.76567(18) 0.0754(2) 0.0321(6) Uani 1 1 d . . .
H29 H 0.7453 0.8064 0.0774 0.039 Uiso 1 1 calc R . .
C30 C 0.76557(14) 0.67838(18) 0.08178(19) 0.0295(6) Uani 1 1 d . . .
C31 C 1.03004(14) 0.70170(18) 0.05576(18) 0.0292(6) Uani 1 1 d . . .
C32 C 0.84898(15) 0.79032(17) 0.06633(19) 0.0307(6) Uani 1 1 d . . .
H32 H 0.8591 0.8483 0.0612 0.037 Uiso 1 1 calc R . .
C33 C 0.94926(15) 0.58409(18) 0.06963(19) 0.0314(6) Uani 1 1 d . . .
H33 H 0.9418 0.5255 0.0748 0.038 Uiso 1 1 calc R . .
C34 C 0.71556(15) 0.49341(17) -0.0095(2) 0.0312(6) Uani 1 1 d . . .
C35 C 1.01666(15) 0.61346(18) 0.06239(19) 0.0308(6) Uani 1 1 d . . .
H35 H 1.0543 0.5747 0.0618 0.037 Uiso 1 1 calc R . .
C36 C 1.10168(16) 0.73144(19) 0.04680(19) 0.0331(6) Uani 1 1 d . . .
C37 C 0.59051(16) 0.4675(2) -0.0602(2) 0.0418(7) Uani 1 1 d . . .
H37 H 0.5438 0.4629 -0.0454 0.050 Uiso 1 1 calc R . .
C38 C 0.61511(17) 0.7301(2) -0.0182(2) 0.0436(8) Uani 1 1 d . . .
H38 H 0.6361 0.7073 -0.0690 0.052 Uiso 1 1 calc R . .
C39 C 0.64097(15) 0.70924(19) 0.0755(2) 0.0357(7) Uani 1 1 d . . .
C40 C 0.64589(15) 0.48770(19) 0.0120(2) 0.0367(7) Uani 1 1 d . . .
H40 H 0.6366 0.4974 0.0748 0.044 Uiso 1 1 calc R . .
C41 C 0.72921(18) 0.4803(2) -0.1035(2) 0.0437(8) Uani 1 1 d . . .
H41 H 0.7759 0.4842 -0.1185 0.052 Uiso 1 1 calc R . .
C42 C 0.55734(17) 0.7855(2) -0.0362(3) 0.0480(8) Uani 1 1 d . . .
H42 H 0.5388 0.7999 -0.0994 0.058 Uiso 1 1 calc R . .
C43 C 0.52750(16) 0.8193(2) 0.0396(3) 0.0449(8) Uani 1 1 d . . .
C44 C 0.6724(2) 0.4613(2) -0.1739(2) 0.0520(9) Uani 1 1 d . . .
H44 H 0.6813 0.4532 -0.2371 0.062 Uiso 1 1 calc R . .
C45 C 0.61060(18) 0.7419(2) 0.1517(2) 0.0510(9) Uani 1 1 d . . .
H45 H 0.6283 0.7265 0.2149 0.061 Uiso 1 1 calc R . .
C46 C 0.60280(18) 0.4538(2) -0.1542(2) 0.0432(8) Uani 1 1 d . . .
C47 C 0.55362(19) 0.7976(3) 0.1327(3) 0.0581(10) Uani 1 1 d . . .
H47 H 0.5328 0.8207 0.1835 0.070 Uiso 1 1 calc R . .
Cl1 Cl 0.45947(4) 0.87623(6) 0.33820(7) 0.0503(2) Uani 1 1 d . . .
Cl2 Cl 0.45570(5) 0.89021(7) 0.01704(9) 0.0716(3) Uani 1 1 d . . .
N1 N -0.25627(15) 0.8084(2) 0.3241(2) 0.0510(7) Uani 1 1 d . . .
N2 N 1.15770(14) 0.75569(18) 0.03880(19) 0.0429(6) Uani 1 1 d . . .
O1 O 0.04449(10) 0.48152(12) 0.34632(16) 0.0391(5) Uani 1 1 d . . .
O2 O 0.12778(11) 0.50440(12) 0.22824(14) 0.0384(5) Uani 1 1 d . . .
O3 O 0.19951(10) 0.66281(12) 0.28750(15) 0.0350(5) Uani 1 1 d . . .
O4 O 0.84532(11) 0.45221(13) 0.0586(2) 0.0541(7) Uani 1 1 d . . .
O5 O 0.76435(12) 0.49452(16) 0.17439(16) 0.0534(6) Uani 1 1 d . . .
O6 O 0.69820(10) 0.65158(13) 0.09650(15) 0.0396(5) Uani 1 1 d . . .
S1 S 0.10268(4) 0.52988(4) 0.31645(5) 0.02921(16) Uani 1 1 d . . .
S2 S 0.78887(4) 0.50705(5) 0.08304(6) 0.03615(19) Uani 1 1 d . . .


_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
C48 C46 1.544(4) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C1 N1 1.136(4) . ?
C1 C2 1.445(4) . ?
C2 C3 1.362(4) . ?
C2 C7 1.414(4) . ?
C3 C4 1.410(4) . ?
C3 H3 0.9300 . ?
C4 C8 1.410(4) . ?
C4 C5 1.430(4) . ?
C5 C6 1.422(4) . ?
C5 C11 1.433(4) . ?
C6 C7 1.363(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.354(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(4) . ?
C9 H9 0.9300 . ?
C10 O3 1.365(3) . ?
C10 C11 1.384(4) . ?
C11 S1 1.783(3) . ?
C12 C13 1.366(4) . ?
C12 C15 1.385(4) . ?
C12 O3 1.399(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C17 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 Cl1 1.743(3) . ?
C18 H101 0.84(7) . ?
C18 C19 1.511(5) . ?
C18 H101 0.84(7) . ?
C18 H102 0.86(5) . ?
C18 H100 0.90(6) . ?
C19 C24 1.388(4) . ?
C19 C20 1.394(4) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(4) . ?
C22 S1 1.770(3) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C32 1.407(4) . ?
C25 C27 1.411(4) . ?
C25 C28 1.428(4) . ?
C26 C30 1.384(4) . ?
C26 C28 1.437(4) . ?
C26 S2 1.786(3) . ?
C27 C31 1.367(4) . ?
C27 H27 0.9300 . ?
C28 C33 1.421(4) . ?
C29 C32 1.350(4) . ?
C29 C30 1.400(4) . ?
C29 H29 0.9300 . ?
C30 O6 1.373(3) . ?
C31 C35 1.406(4) . ?
C31 C36 1.443(4) . ?
C32 H32 0.9300 . ?
C33 C35 1.361(4) . ?
C33 H33 0.9300 . ?
C34 C40 1.384(4) . ?
C34 C41 1.388(4) . ?
C34 S2 1.760(3) . ?
C35 H35 0.9300 . ?
C36 N2 1.137(4) . ?
C37 C40 1.377(4) . ?
C37 C46 1.382(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.369(4) . ?
C38 C42 1.381(4) . ?
C38 H38 0.9300 . ?
C39 C45 1.375(4) . ?
C39 O6 1.399(3) . ?
C40 H40 0.9300 . ?
C41 C44 1.375(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.371(5) . ?
C42 H42 0.9300 . ?
C43 C47 1.366(5) . ?
C43 Cl2 1.737(3) . ?
C44 C46 1.376(5) . ?
C44 H44 0.9300 . ?
C45 C47 1.374(5) . ?
C45 H45 0.9300 . ?
C47 H47 0.9300 . ?
O1 S1 1.437(2) . ?
O2 S1 1.437(2) . ?
O4 S2 1.440(2) . ?
O5 S2 1.430(2) . ?

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
C46 C48 H48A 109.5 . . ?
C46 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C46 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N1 C1 C2 178.9(4) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 121.0(3) . . ?
C7 C2 C1 119.3(3) . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C8 119.7(2) . . ?
C3 C4 C5 120.3(2) . . ?
C8 C4 C5 120.0(2) . . ?
C6 C5 C4 116.9(2) . . ?
C6 C5 C11 125.8(2) . . ?
C4 C5 C11 117.3(2) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C9 C8 C4 121.8(2) . . ?
C9 C8 H8 119.1 . . ?
C4 C8 H8 119.1 . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
O3 C10 C11 117.3(2) . . ?
O3 C10 C9 121.2(2) . . ?
C11 C10 C9 121.5(2) . . ?
C10 C11 C5 120.1(2) . . ?
C10 C11 S1 116.2(2) . . ?
C5 C11 S1 123.68(19) . . ?
C13 C12 C15 121.4(3) . . ?
C13 C12 O3 120.3(3) . . ?
C15 C12 O3 118.1(3) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C17 C14 C13 119.3(3) . . ?
C17 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C12 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C12 C15 H15 120.5 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C14 121.5(3) . . ?
C16 C17 Cl1 119.0(2) . . ?
C14 C17 Cl1 119.4(2) . . ?
H101 C18 C19 115(5) . . ?
H101 C18 H101 0(10) . . ?
C19 C18 H101 115(5) . . ?
H101 C18 H102 102(5) . . ?
C19 C18 H102 111(4) . . ?
H101 C18 H102 102(5) . . ?
H101 C18 H100 117(5) . . ?
C19 C18 H100 109(3) . . ?
H101 C18 H100 117(5) . . ?
H102 C18 H100 102(5) . . ?
C24 C19 C20 118.4(3) . . ?
C24 C19 C18 120.6(3) . . ?
C20 C19 C18 121.0(3) . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 119.0(3) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 S1 119.3(2) . . ?
C21 C22 S1 119.3(2) . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C19 121.3(3) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C32 C25 C27 119.5(2) . . ?
C32 C25 C28 120.2(2) . . ?
C27 C25 C28 120.3(2) . . ?
C30 C26 C28 119.3(2) . . ?
C30 C26 S2 117.1(2) . . ?
C28 C26 S2 123.6(2) . . ?
C31 C27 C25 120.4(3) . . ?
C31 C27 H27 119.8 . . ?
C25 C27 H27 119.8 . . ?
C33 C28 C25 117.0(2) . . ?
C33 C28 C26 125.5(2) . . ?
C25 C28 C26 117.5(2) . . ?
C32 C29 C30 119.5(3) . . ?
C32 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
O6 C30 C26 117.2(2) . . ?
O6 C30 C29 120.8(2) . . ?
C26 C30 C29 122.0(3) . . ?
C27 C31 C35 119.9(3) . . ?
C27 C31 C36 120.2(3) . . ?
C35 C31 C36 119.9(3) . . ?
C29 C32 C25 121.4(3) . . ?
C29 C32 H32 119.3 . . ?
C25 C32 H32 119.3 . . ?
C35 C33 C28 121.6(3) . . ?
C35 C33 H33 119.2 . . ?
C28 C33 H33 119.2 . . ?
C40 C34 C41 120.2(3) . . ?
C40 C34 S2 120.7(2) . . ?
C41 C34 S2 118.9(2) . . ?
C33 C35 C31 120.7(3) . . ?
C33 C35 H35 119.6 . . ?
C31 C35 H35 119.6 . . ?
N2 C36 C31 179.0(3) . . ?
C40 C37 C46 121.4(3) . . ?
C40 C37 H37 119.3 . . ?
C46 C37 H37 119.3 . . ?
C39 C38 C42 119.0(3) . . ?
C39 C38 H38 120.5 . . ?
C42 C38 H38 120.5 . . ?
C38 C39 C45 121.6(3) . . ?
C38 C39 O6 120.7(3) . . ?
C45 C39 O6 117.8(3) . . ?
C37 C40 C34 119.4(3) . . ?
C37 C40 H40 120.3 . . ?
C34 C40 H40 120.3 . . ?
C44 C41 C34 118.7(3) . . ?
C44 C41 H41 120.6 . . ?
C34 C41 H41 120.6 . . ?
C43 C42 C38 119.8(3) . . ?
C43 C42 H42 120.1 . . ?
C38 C42 H42 120.1 . . ?
C47 C43 C42 120.7(3) . . ?
C47 C43 Cl2 119.6(3) . . ?
C42 C43 Cl2 119.8(3) . . ?
C41 C44 C46 122.3(3) . . ?
C41 C44 H44 118.8 . . ?
C46 C44 H44 118.9 . . ?
C47 C45 C39 118.8(3) . . ?
C47 C45 H45 120.6 . . ?
C39 C45 H45 120.6 . . ?
C44 C46 C37 117.9(3) . . ?
C44 C46 C48 120.7(3) . . ?
C37 C46 C48 121.4(3) . . ?
C43 C47 C45 120.2(3) . . ?
C43 C47 H47 119.9 . . ?
C45 C47 H47 119.9 . . ?
C10 O3 C12 118.6(2) . . ?
C30 O6 C39 117.8(2) . . ?
O1 S1 O2 117.29(12) . . ?
O1 S1 C22 106.04(13) . . ?
O2 S1 C22 108.54(13) . . ?
O1 S1 C11 109.45(12) . . ?
O2 S1 C11 109.18(12) . . ?
C22 S1 C11 105.69(12) . . ?
O5 S2 O4 118.11(15) . . ?
O5 S2 C34 108.80(13) . . ?
O4 S2 C34 106.05(14) . . ?
O5 S2 C26 108.03(14) . . ?
O4 S2 C26 108.71(13) . . ?
C34 S2 C26 106.58(12) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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 1502491'
_audit_update_record             
;
2016-09-04 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8.50 F1.50 O2 S'
_chemical_formula_weight         233.24

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'

_space_group_crystal_system      ??Monoclinic??
_space_group_IT_number           14
_space_group_name_H-M_alt        P2(1)/c
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0792(9)
_cell_length_b                   14.673(2)
_cell_length_c                   23.976(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.386(4)
_cell_angle_gamma                90
_cell_volume                     2138.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8190
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      24.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.302
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31921
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.776
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3763
_reflns_number_gt                2648
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+2.3315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3763
_refine_ls_number_parameters     336
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.00134(15) 0.17499(6) 0.36391(4) 0.0518(3) Uani 1 1 d . . . . .
O1 O 0.3854(5) 0.21147(18) 0.43714(11) 0.0659(7) Uani 1 1 d . . . . .
H1 H 0.4846 0.2225 0.4599 0.099 Uiso 1 1 calc R U . . .
C1 C 0.2335(6) 0.1473(2) 0.32381(13) 0.0475(8) Uani 1 1 d . . . . .
C2 C 0.3580(5) 0.0719(2) 0.33276(13) 0.0467(8) Uani 1 1 d . . . . .
H2 H 0.3265 0.0326 0.3619 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5356(6) 0.0534(2) 0.29771(13) 0.0484(9) Uani 1 1 d . . . . .
C4 C 0.6715(6) -0.0230(3) 0.30634(16) 0.0597(10) Uani 1 1 d . . . . .
H4 H 0.6400 -0.0645 0.3343 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8491(7) -0.0365(3) 0.27392(19) 0.0736(12) Uani 1 1 d . . . . .
H5 H 0.9399 -0.0866 0.2804 0.088 Uiso 1 1 calc R U . . .
C6 C 0.8964(7) 0.0239(4) 0.23111(19) 0.0782(13) Uani 1 1 d . . . . .
H6 H 1.0179 0.0134 0.2091 0.094 Uiso 1 1 calc R U . . .
C7 C 0.7683(7) 0.0973(3) 0.22112(16) 0.0725(13) Uani 1 1 d . . . . .
H7 H 0.8022 0.1369 0.1923 0.087 Uiso 1 1 calc R U . . .
C8 C 0.5821(6) 0.1149(3) 0.25414(14) 0.0557(10) Uani 1 1 d . . . . .
C9 C 0.4458(7) 0.1913(3) 0.24576(15) 0.0641(11) Uani 1 1 d . . . . .
H9 H 0.4737 0.2312 0.2166 0.077 Uiso 1 1 calc R U . . .
C10 C 0.2744(7) 0.2077(3) 0.27944(15) 0.0624(10) Uani 1 1 d . . . . .
H10 H 0.1846 0.2582 0.2734 0.075 Uiso 1 1 calc R U . . .
C11 C -0.0123(7) 0.0924(3) 0.41842(17) 0.0690(11) Uani 1 1 d . . . . .
H11A H 0.1270 0.0894 0.4380 0.104 Uiso 1 1 calc R U . . .
H11B H -0.0466 0.0338 0.4027 0.104 Uiso 1 1 calc R U . . .
H11C H -0.1247 0.1095 0.4438 0.104 Uiso 1 1 calc R U . . .
C12 C 0.0714(5) 0.2789(2) 0.39654(13) 0.0436(8) Uani 1 1 d . . . . .
C13 C -0.0703(6) 0.3545(2) 0.38680(13) 0.0461(8) Uani 1 1 d . . . . .
C14 C -0.2619(6) 0.3522(3) 0.35210(15) 0.0577(10) Uani 1 1 d . . . . .
H14 H -0.2999 0.2987 0.3334 0.069 Uiso 1 1 calc R U . . .
C15 C -0.3914(7) 0.4275(3) 0.34573(18) 0.0721(12) Uani 1 1 d . . . . .
H15 H -0.5162 0.4247 0.3226 0.087 Uiso 1 1 calc R U . . .
C16 C -0.3397(8) 0.5081(3) 0.37324(19) 0.0758(13) Uani 1 1 d . . . . .
H16 H -0.4310 0.5586 0.3691 0.091 Uiso 1 1 calc R U . . .
C17 C -0.1570(8) 0.5130(3) 0.40597(16) 0.0672(12) Uani 1 1 d . . . . .
H17 H -0.1230 0.5676 0.4239 0.081 Uiso 1 1 calc R U . . .
C18 C -0.0157(6) 0.4374(2) 0.41376(13) 0.0499(9) Uani 1 1 d . . . . .
C19 C 0.1751(7) 0.4413(3) 0.44806(15) 0.0603(10) Uani 1 1 d . . . . .
H19 H 0.2114 0.4960 0.4656 0.072 Uiso 1 1 calc R U . . .
C20 C 0.3067(6) 0.3688(3) 0.45641(15) 0.0590(10) Uani 1 1 d . . . . .
H20 H 0.4312 0.3740 0.4795 0.071 Uiso 1 1 calc R U . . .
C21 C 0.2575(6) 0.2853(2) 0.43058(14) 0.0503(9) Uani 1 1 d . . . . .
S S 0.70691(18) 0.21442(11) 0.57255(5) 0.0841(4) Uani 1 1 d . . . . .
O2 O 0.6620(15) 0.1848(5) 0.5222(4) 0.081(2) Uani 0.5 1 d . . P A 1
O3 O 0.6843(14) 0.3214(5) 0.5794(4) 0.106(3) Uani 0.5 1 d . U P A 1
O4 O 0.6135(19) 0.2596(13) 0.6077(5) 0.154(4) Uani 0.5 1 d . U P A 1
C22 C 0.9979(7) 0.2051(3) 0.58461(19) 0.0647(11) Uani 1 1 d . . . . .
F1 F 1.0695(9) 0.2420(6) 0.6325(3) 0.0848(18) Uani 0.5 1 d . . P B 1
F2 F 1.1087(10) 0.2541(5) 0.5461(3) 0.089(2) Uani 0.5 1 d . . P B 1
F3 F 1.0608(15) 0.1241(4) 0.5806(5) 0.099(3) Uani 0.5 1 d . U P B 1
F4 F 1.0309(16) 0.1719(10) 0.6350(4) 0.161(4) Uani 0.5 1 d . U P B 2
F5 F 1.0833(19) 0.2732(7) 0.5837(7) 0.167(4) Uani 0.5 1 d . U P B 2
F6 F 1.0945(18) 0.1465(9) 0.5537(4) 0.139(4) Uani 0.5 1 d . U P B 2
O6 O 0.6421(16) 0.1113(8) 0.5734(6) 0.175(5) Uani 0.5 1 d . . P A 2
O5 O 0.6253(16) 0.1754(10) 0.6213(4) 0.135(4) Uani 0.5 1 d . . P A 2
O7 O 0.7031(17) 0.2368(6) 0.5133(4) 0.097(3) Uani 0.5 1 d . . P 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
S1 C12 1.762(3) . ?
S1 C1 1.774(4) . ?
S1 C11 1.786(4) . ?
O1 C21 1.341(4) . ?
O1 H1 0.8200 . ?
C1 C2 1.354(5) . ?
C1 C10 1.412(5) . ?
C2 C3 1.411(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(5) . ?
C3 C8 1.415(5) . ?
C4 C5 1.360(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.348(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.421(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(5) . ?
C9 C10 1.355(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C21 1.382(5) . ?
C12 C13 1.419(5) . ?
C13 C18 1.414(5) . ?
C13 C14 1.415(5) . ?
C14 C15 1.362(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.346(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.407(5) . ?
C19 C20 1.343(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.402(5) . ?
C20 H20 0.9300 . ?
S O4 1.223(9) . ?
S O2 1.305(8) . ?
S O5 1.403(8) . ?
S O7 1.458(9) . ?
S O6 1.564(10) . ?
S O3 1.585(7) . ?
S C22 1.791(5) . ?
O3 O4 1.217(16) . ?
C22 F5 1.127(9) . ?
C22 F3 1.252(9) . ?
C22 F6 1.287(11) . ?
C22 F4 1.313(9) . ?
C22 F1 1.334(7) . ?
C22 F2 1.362(7) . ?
O6 O5 1.490(15) . ?

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
C12 S1 C1 104.61(16) . . ?
C12 S1 C11 106.12(17) . . ?
C1 S1 C11 107.01(18) . . ?
C21 O1 H1 109.5 . . ?
C2 C1 C10 121.6(3) . . ?
C2 C1 S1 123.4(3) . . ?
C10 C1 S1 114.9(3) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 C8 119.4(3) . . ?
C2 C3 C8 119.1(3) . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C3 119.1(3) . . ?
C9 C8 C7 122.7(4) . . ?
C3 C8 C7 118.1(4) . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C1 119.3(4) . . ?
C9 C10 H10 120.4 . . ?
C1 C10 H10 120.4 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C12 C13 121.9(3) . . ?
C21 C12 S1 120.4(3) . . ?
C13 C12 S1 117.6(2) . . ?
C18 C13 C14 118.0(3) . . ?
C18 C13 C12 117.5(3) . . ?
C14 C13 C12 124.5(3) . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.9(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.7(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 122.4(4) . . ?
C19 C18 C13 118.9(3) . . ?
C17 C18 C13 118.7(4) . . ?
C20 C19 C18 122.3(3) . . ?
C20 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C19 C20 C21 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O1 C21 C12 118.6(3) . . ?
O1 C21 C20 122.5(3) . . ?
C12 C21 C20 118.9(3) . . ?
O4 S O2 136.7(7) . . ?
O5 S O7 155.0(5) . . ?
O5 S O6 60.0(6) . . ?
O7 S O6 103.4(7) . . ?
O4 S O3 49.3(8) . . ?
O2 S O3 114.2(5) . . ?
O4 S C22 113.8(6) . . ?
O2 S C22 107.9(4) . . ?
O5 S C22 101.7(5) . . ?
O7 S C22 99.6(4) . . ?
O6 S C22 99.9(4) . . ?
O3 S C22 98.4(3) . . ?
O4 O3 S 49.6(5) . . ?
O3 O4 S 81.0(9) . . ?
F5 C22 F6 111.4(10) . . ?
F5 C22 F4 106.7(9) . . ?
F6 C22 F4 102.8(8) . . ?
F3 C22 F1 110.9(6) . . ?
F3 C22 F2 107.0(7) . . ?
F1 C22 F2 102.3(6) . . ?
F5 C22 S 112.5(7) . . ?
F3 C22 S 111.3(5) . . ?
F6 C22 S 114.9(6) . . ?
F4 C22 S 107.8(5) . . ?
F1 C22 S 114.1(4) . . ?
F2 C22 S 110.6(4) . . ?
O5 O6 S 54.6(5) . . ?
S O5 O6 65.4(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
C12 S1 C1 C2 117.2(3) . . . . ?
C11 S1 C1 C2 4.9(3) . . . . ?
C12 S1 C1 C10 -65.7(3) . . . . ?
C11 S1 C1 C10 -178.1(3) . . . . ?
C10 C1 C2 C3 1.0(5) . . . . ?
S1 C1 C2 C3 177.9(2) . . . . ?
C1 C2 C3 C4 178.6(3) . . . . ?
C1 C2 C3 C8 0.9(5) . . . . ?
C2 C3 C4 C5 -176.2(3) . . . . ?
C8 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 -1.3(6) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C4 C3 C8 C9 -179.9(3) . . . . ?
C2 C3 C8 C9 -2.1(5) . . . . ?
C4 C3 C8 C7 -0.9(5) . . . . ?
C2 C3 C8 C7 176.9(3) . . . . ?
C6 C7 C8 C9 179.1(4) . . . . ?
C6 C7 C8 C3 0.1(5) . . . . ?
C3 C8 C9 C10 1.5(5) . . . . ?
C7 C8 C9 C10 -177.5(4) . . . . ?
C8 C9 C10 C1 0.4(6) . . . . ?
C2 C1 C10 C9 -1.7(5) . . . . ?
S1 C1 C10 C9 -178.8(3) . . . . ?
C1 S1 C12 C21 -58.0(3) . . . . ?
C11 S1 C12 C21 55.0(3) . . . . ?
C1 S1 C12 C13 122.5(3) . . . . ?
C11 S1 C12 C13 -124.6(3) . . . . ?
C21 C12 C13 C18 -0.6(5) . . . . ?
S1 C12 C13 C18 179.0(2) . . . . ?
C21 C12 C13 C14 179.5(3) . . . . ?
S1 C12 C13 C14 -0.9(4) . . . . ?
C18 C13 C14 C15 -1.1(5) . . . . ?
C12 C13 C14 C15 178.8(3) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C17 1.2(6) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 C19 -179.6(4) . . . . ?
C16 C17 C18 C13 -0.7(5) . . . . ?
C14 C13 C18 C19 -179.5(3) . . . . ?
C12 C13 C18 C19 0.6(5) . . . . ?
C14 C13 C18 C17 1.6(5) . . . . ?
C12 C13 C18 C17 -178.3(3) . . . . ?
C17 C18 C19 C20 178.5(3) . . . . ?
C13 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C13 C12 C21 O1 -179.0(3) . . . . ?
S1 C12 C21 O1 1.5(5) . . . . ?
C13 C12 C21 C20 0.3(5) . . . . ?
S1 C12 C21 C20 -179.2(3) . . . . ?
C19 C20 C21 O1 179.2(3) . . . . ?
C19 C20 C21 C12 -0.1(5) . . . . ?
O2 S O3 O4 131.7(9) . . . . ?
C22 S O3 O4 -114.2(8) . . . . ?
O2 S O4 O3 -82.9(14) . . . . ?
C22 S O4 O3 80.4(8) . . . . ?
O5 S C22 F5 -121.6(12) . . . . ?
O7 S C22 F5 71.7(11) . . . . ?
O6 S C22 F5 177.3(12) . . . . ?
O4 S C22 F3 131.8(12) . . . . ?
O2 S C22 F3 -60.2(8) . . . . ?
O3 S C22 F3 -179.1(7) . . . . ?
O5 S C22 F6 109.6(9) . . . . ?
O7 S C22 F6 -57.1(8) . . . . ?
O6 S C22 F6 48.4(9) . . . . ?
O5 S C22 F4 -4.3(10) . . . . ?
O7 S C22 F4 -171.0(8) . . . . ?
O6 S C22 F4 -65.4(9) . . . . ?
O4 S C22 F1 5.4(12) . . . . ?
O2 S C22 F1 173.3(7) . . . . ?
O3 S C22 F1 54.5(7) . . . . ?
O4 S C22 F2 -109.4(11) . . . . ?
O2 S C22 F2 58.6(6) . . . . ?
O3 S C22 F2 -60.3(6) . . . . ?
O7 S O6 O5 -159.7(7) . . . . ?
C22 S O6 O5 97.8(6) . . . . ?
O7 S O5 O6 53(2) . . . . ?
C22 S O5 O6 -94.8(5) . . . . ?

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.048

