# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c2221
_database_code_depnum_ccdc_archive 'CCDC 1020179'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.32

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   C222(1)

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

_cell_length_a                   11.088(2)
_cell_length_b                   18.565(4)
_cell_length_c                   13.258(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2729.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    897
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      30.5

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15171
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         30.58
_reflns_number_total             4184
_reflns_number_gt                3602
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0692P)²+0.4730P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(15)
_refine_ls_number_reflns         4184
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
O1A O 0.66829(11) 0.60110(6) 0.37501(8) 0.0373(3) Uani 1 1 d . . .
C1A C 0.59058(11) 0.55457(6) 0.37572(10) 0.0242(2) Uani 1 1 d . . .
C2A C 0.45660(11) 0.56751(6) 0.37091(9) 0.0224(2) Uani 1 1 d . . .
C3A C 0.40592(10) 0.50146(6) 0.37274(9) 0.0180(2) Uani 1 1 d . . .
C4A C 0.28991(10) 0.46432(6) 0.37070(9) 0.0216(2) Uani 1 1 d . . .
C5A C 0.17026(12) 0.48614(9) 0.36572(11) 0.0328(3) Uani 1 1 d . . .
C6A C 0.08144(13) 0.43095(11) 0.36460(12) 0.0452(4) Uani 1 1 d . . .
H6A H -0.0009 0.4450 0.3618 0.054 Uiso 1 1 calc R . .
C7A C 0.10679(14) 0.35941(11) 0.36733(13) 0.0459(4) Uani 1 1 d . . .
H7A H 0.0430 0.3253 0.3658 0.055 Uiso 1 1 calc R . .
C8A C 0.22829(14) 0.33534(8) 0.37244(11) 0.0360(3) Uani 1 1 d . . .
C9A C 0.26984(19) 0.26310(8) 0.37621(12) 0.0451(4) Uani 1 1 d . . .
H9A H 0.2136 0.2245 0.3751 0.054 Uiso 1 1 calc R . .
C10A C 0.39048(18) 0.24888(7) 0.38150(11) 0.0429(4) Uani 1 1 d . . .
H10A H 0.4151 0.1999 0.3842 0.052 Uiso 1 1 calc R . .
C11A C 0.48149(15) 0.30276(7) 0.38322(9) 0.0311(3) Uani 1 1 d . . .
C12A C 0.44273(11) 0.37392(6) 0.37858(9) 0.0209(2) Uani 1 1 d . . .
C13A C 0.50367(10) 0.44385(6) 0.37833(9) 0.0181(2) Uani 1 1 d . . .
C14A C 0.61342(10) 0.47448(6) 0.38043(10) 0.0219(2) Uani 1 1 d . . .
C15A C 0.31749(11) 0.38939(6) 0.37410(9) 0.0229(2) Uani 1 1 d . . .
C16A C 0.40900(16) 0.64278(7) 0.36541(11) 0.0334(3) Uani 1 1 d . . .
H16A H 0.3710 0.6506 0.2996 0.050 Uiso 1 1 calc R . .
H16B H 0.4756 0.6769 0.3742 0.050 Uiso 1 1 calc R . .
H16C H 0.3492 0.6501 0.4189 0.050 Uiso 1 1 calc R . .
C17A C 0.13253(14) 0.56359(10) 0.35973(14) 0.0452(4) Uani 1 1 d . . .
H17A H 0.1647 0.5898 0.4180 0.068 Uiso 1 1 calc R . .
H17B H 0.0443 0.5666 0.3599 0.068 Uiso 1 1 calc R . .
H17C H 0.1639 0.5849 0.2974 0.068 Uiso 1 1 calc R . .
C18A C 0.61182(17) 0.28172(8) 0.39032(13) 0.0431(4) Uani 1 1 d . . .
H18A H 0.6530 0.2943 0.3273 0.065 Uiso 1 1 calc R . .
H18B H 0.6180 0.2297 0.4016 0.065 Uiso 1 1 calc R . .
H18C H 0.6496 0.3074 0.4466 0.065 Uiso 1 1 calc R . .
C19A C 0.74030(11) 0.44767(9) 0.38532(10) 0.0326(3) Uani 1 1 d . . .
H19A H 0.7546 0.4251 0.4511 0.049 Uiso 1 1 calc R . .
H19B H 0.7960 0.4881 0.3764 0.049 Uiso 1 1 calc R . .
H19C H 0.7535 0.4122 0.3317 0.049 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
O1A C1A 1.2201(14) . ?
C1A C2A 1.5063(18) . ?
C1A C14A 1.5096(17) . ?
C2A C3A 1.3490(15) . ?
C2A C16A 1.4955(17) . ?
C3A C4A 1.4597(16) . ?
C3A C13A 1.5245(15) . ?
C4A C5A 1.3888(18) . ?
C4A C15A 1.4249(17) . ?
C5A C6A 1.421(2) . ?
C5A C17A 1.500(2) . ?
C6A C7A 1.358(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.421(3) . ?
C7A H7A 0.9500 . ?
C8A C15A 1.4091(16) . ?
C8A C9A 1.419(2) . ?
C9A C10A 1.365(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.421(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3906(17) . ?
C11A C18A 1.500(2) . ?
C12A C15A 1.4194(18) . ?
C12A C13A 1.4635(15) . ?
C13A C14A 1.3436(16) . ?
C14A C19A 1.4937(17) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?

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
O1A C1A C2A 125.69(12) . . ?
O1A C1A C14A 125.39(12) . . ?
C2A C1A C14A 108.92(9) . . ?
C3A C2A C16A 134.69(13) . . ?
C3A C2A C1A 105.38(10) . . ?
C16A C2A C1A 119.94(11) . . ?
C2A C3A C4A 142.75(11) . . ?
C2A C3A C13A 110.02(10) . . ?
C4A C3A C13A 107.22(9) . . ?
C5A C4A C15A 119.42(12) . . ?
C5A C4A C3A 134.83(12) . . ?
C15A C4A C3A 105.75(10) . . ?
C4A C5A C6A 116.89(15) . . ?
C4A C5A C17A 123.28(14) . . ?
C6A C5A C17A 119.83(13) . . ?
C7A C6A C5A 124.15(14) . . ?
C7A C6A H6A 117.9 . . ?
C5A C6A H6A 117.9 . . ?
C6A C7A C8A 120.34(13) . . ?
C6A C7A H7A 119.8 . . ?
C8A C7A H7A 119.8 . . ?
C15A C8A C9A 116.40(14) . . ?
C15A C8A C7A 116.24(14) . . ?
C9A C8A C7A 127.35(14) . . ?
C10A C9A C8A 120.18(12) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 124.08(14) . . ?
C9A C10A H10A 118.0 . . ?
C11A C10A H10A 118.0 . . ?
C12A C11A C10A 116.65(15) . . ?
C12A C11A C18A 123.22(13) . . ?
C10A C11A C18A 120.13(13) . . ?
C11A C12A C15A 119.76(11) . . ?
C11A C12A C13A 134.44(12) . . ?
C15A C12A C13A 105.79(10) . . ?
C14A C13A C12A 142.52(11) . . ?
C14A C13A C3A 110.37(10) . . ?
C12A C13A C3A 107.11(10) . . ?
C13A C14A C19A 135.48(12) . . ?
C13A C14A C1A 105.31(10) . . ?
C19A C14A C1A 119.21(11) . . ?
C8A C15A C12A 122.91(12) . . ?
C8A C15A C4A 122.96(13) . . ?
C12A C15A C4A 114.13(10) . . ?
C2A C16A H16A 109.5 . . ?
C2A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C2A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C5A C17A H17A 109.5 . . ?
C5A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C5A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C11A C18A H18A 109.5 . . ?
C11A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C11A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C14A C19A H19A 109.5 . . ?
C14A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C14A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 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
O1A C1A C2A C3A 179.44(13) . . . . ?
C14A C1A C2A C3A 0.07(14) . . . . ?
O1A C1A C2A C16A -0.5(2) . . . . ?
C14A C1A C2A C16A -179.84(12) . . . . ?
C16A C2A C3A C4A 0.2(3) . . . . ?
C1A C2A C3A C4A -179.70(16) . . . . ?
C16A C2A C3A C13A 179.68(14) . . . . ?
C1A C2A C3A C13A -0.21(13) . . . . ?
C2A C3A C4A C5A -0.3(3) . . . . ?
C13A C3A C4A C5A -179.81(14) . . . . ?
C2A C3A C4A C15A 179.08(16) . . . . ?
C13A C3A C4A C15A -0.41(13) . . . . ?
C15A C4A C5A C6A 0.2(2) . . . . ?
C3A C4A C5A C6A 179.50(14) . . . . ?
C15A C4A C5A C17A -178.70(13) . . . . ?
C3A C4A C5A C17A 0.6(3) . . . . ?
C4A C5A C6A C7A -0.5(2) . . . . ?
C17A C5A C6A C7A 178.40(16) . . . . ?
C5A C6A C7A C8A 0.5(3) . . . . ?
C6A C7A C8A C15A -0.2(2) . . . . ?
C6A C7A C8A C9A 179.71(15) . . . . ?
C15A C8A C9A C10A 0.2(2) . . . . ?
C7A C8A C9A C10A -179.67(14) . . . . ?
C8A C9A C10A C11A -0.3(3) . . . . ?
C9A C10A C11A C12A -0.4(2) . . . . ?
C9A C10A C11A C18A 179.30(14) . . . . ?
C10A C11A C12A C15A 0.99(18) . . . . ?
C18A C11A C12A C15A -178.67(13) . . . . ?
C10A C11A C12A C13A 179.99(14) . . . . ?
C18A C11A C12A C13A 0.3(2) . . . . ?
C11A C12A C13A C14A 1.3(3) . . . . ?
C15A C12A C13A C14A -179.58(16) . . . . ?
C11A C12A C13A C3A -179.45(14) . . . . ?
C15A C12A C13A C3A -0.35(13) . . . . ?
C2A C3A C13A C14A 0.31(14) . . . . ?
C4A C3A C13A C14A 179.98(10) . . . . ?
C2A C3A C13A C12A -179.19(10) . . . . ?
C4A C3A C13A C12A 0.48(13) . . . . ?
C12A C13A C14A C19A -0.6(3) . . . . ?
C3A C13A C14A C19A -179.81(14) . . . . ?
C12A C13A C14A C1A 178.97(16) . . . . ?
C3A C13A C14A C1A -0.24(13) . . . . ?
O1A C1A C14A C13A -179.26(14) . . . . ?
C2A C1A C14A C13A 0.12(14) . . . . ?
O1A C1A C14A C19A 0.4(2) . . . . ?
C2A C1A C14A C19A 179.77(11) . . . . ?
C9A C8A C15A C12A 0.4(2) . . . . ?
C7A C8A C15A C12A -179.67(13) . . . . ?
C9A C8A C15A C4A 179.96(14) . . . . ?
C7A C8A C15A C4A -0.1(2) . . . . ?
C11A C12A C15A C8A -1.1(2) . . . . ?
C13A C12A C15A C8A 179.68(11) . . . . ?
C11A C12A C15A C4A 179.36(11) . . . . ?
C13A C12A C15A C4A 0.10(15) . . . . ?
C5A C4A C15A C8A 0.1(2) . . . . ?
C3A C4A C15A C8A -179.37(11) . . . . ?
C5A C4A C15A C12A 179.71(11) . . . . ?
C3A C4A C15A C12A 0.20(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.119
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1020180'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 F8 S'
_chemical_formula_weight         452.40

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.519(6)
_cell_length_b                   12.951(5)
_cell_length_c                   17.522(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.652(7)
_cell_angle_gamma                90
_cell_volume                     3591(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    138(2)
_cell_measurement_reflns_used    979
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      30.5

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.440
_exptl_absorpt_coefficient_mu    0.266
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      138(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28650
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.032
_diffrn_reflns_theta_max         30.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5477
_reflns_number_gt                4294
_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       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0757P)²+3.5647P]
 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         5477
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.002
_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 0.15031(3) 1.12756(3) 0.35140(3) 0.03048(12) Uani 1 1 d . . . . .
F1 F 0.18984(8) 1.18109(8) 0.43472(7) 0.0359(3) Uani 1 1 d . . . . .
F6 F 0.07291(8) 1.15537(8) 0.49257(7) 0.0356(3) Uani 1 1 d . . . . .
F2 F 0.05800(8) 1.15813(9) 0.35187(7) 0.0393(3) Uani 1 1 d . . . . .
F3 F 0.11227(9) 1.08538(9) 0.26388(7) 0.0395(3) Uani 1 1 d . . . . .
F8 F 0.07293(7) 1.03807(8) 0.57543(6) 0.0315(2) Uani 1 1 d . . . . .
F4 F 0.24313(8) 1.10696(8) 0.34599(8) 0.0385(3) Uani 1 1 d . . . . .
F5 F 0.15632(11) 1.23752(9) 0.31219(9) 0.0545(4) Uani 1 1 d . . . . .
F7 F 0.19076(7) 1.11052(8) 0.57680(7) 0.0328(2) Uani 1 1 d . . . . .
C1 C 0.14368(10) 0.99983(11) 0.39614(9) 0.0203(3) Uani 1 1 d . . . . .
C5 C 0.12406(9) 0.69045(11) 0.47297(9) 0.0195(3) Uani 1 1 d . . . . .
C18 C 0.16297(11) 0.87240(13) 0.59710(10) 0.0251(3) Uani 1 1 d . . . . .
H18A H 0.1122 0.8705 0.6153 0.038 Uiso 1 1 calc R U . . .
H18B H 0.1995 0.9293 0.6235 0.038 Uiso 1 1 calc R U . . .
H18C H 0.1936 0.8070 0.6103 0.038 Uiso 1 1 calc R U . . .
C21 C 0.19619(11) 0.90938(12) 0.28513(10) 0.0251(3) Uani 1 1 d . . . . .
H21A H 0.2151 0.8389 0.2791 0.038 Uiso 1 1 calc R U . . .
H21B H 0.2450 0.9560 0.2987 0.038 Uiso 1 1 calc R U . . .
H21C H 0.1560 0.9318 0.2351 0.038 Uiso 1 1 calc R U . . .
C15 C 0.13270(9) 0.81598(11) 0.37788(9) 0.0179(3) Uani 1 1 d . . . . .
C17 C 0.11781(11) 1.07446(13) 0.52813(10) 0.0261(3) Uani 1 1 d . . . . .
C8 C 0.12380(11) 0.47211(12) 0.45725(11) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.1293 0.3992 0.4557 0.034 Uiso 1 1 calc R U . . .
C3 C 0.13780(10) 0.88858(11) 0.50776(9) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.12736(10) 0.53335(11) 0.39142(10) 0.0237(3) Uani 1 1 d . . . . .
C20 C 0.08748(11) 0.73939(13) 0.18803(10) 0.0258(3) Uani 1 1 d . . . . .
H20A H 0.0601 0.8033 0.1977 0.039 Uiso 1 1 calc R U . . .
H20B H 0.0481 0.6999 0.1456 0.039 Uiso 1 1 calc R U . . .
H20C H 0.1380 0.7563 0.1719 0.039 Uiso 1 1 calc R U . . .
C19 C 0.07674(12) 0.66453(13) 0.60070(10) 0.0279(3) Uani 1 1 d . . . . .
H19A H 0.1254 0.6784 0.6469 0.042 Uiso 1 1 calc R U . . .
H19B H 0.0415 0.6107 0.6142 0.042 Uiso 1 1 calc R U . . .
H19C H 0.0434 0.7278 0.5856 0.042 Uiso 1 1 calc R U . . .
C4 C 0.12800(9) 0.80303(11) 0.45726(9) 0.0183(3) Uani 1 1 d . . . . .
C12 C 0.11224(10) 0.67595(11) 0.26315(9) 0.0210(3) Uani 1 1 d . . . . .
C11 C 0.11346(11) 0.56641(12) 0.25325(10) 0.0266(3) Uani 1 1 d . . . . .
H11 H 0.1074 0.5401 0.2013 0.032 Uiso 1 1 calc R U . . .
C14 C 0.13003(10) 0.64068(11) 0.40244(9) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.15349(9) 0.91164(11) 0.35109(9) 0.0189(3) Uani 1 1 d . . . . .
C10 C 0.12287(12) 0.49735(12) 0.31415(11) 0.0280(3) Uani 1 1 d . . . . .
H10 H 0.1264 0.4255 0.3046 0.034 Uiso 1 1 calc R U . . .
C6 C 0.10738(10) 0.62878(12) 0.53203(10) 0.0229(3) Uani 1 1 d . . . . .
C13 C 0.12805(10) 0.71254(11) 0.34054(9) 0.0189(3) Uani 1 1 d . . . . .
C7 C 0.11229(11) 0.51934(13) 0.52298(11) 0.0275(3) Uani 1 1 d . . . . .
H7 H 0.1072 0.4768 0.5655 0.033 Uiso 1 1 calc R U . . .
C2 C 0.13266(10) 0.98831(11) 0.47304(9) 0.0202(3) 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
S1 F2 1.5776(14) . ?
S1 F1 1.5786(13) . ?
S1 F3 1.5789(14) . ?
S1 F4 1.5857(14) . ?
S1 F5 1.5965(13) . ?
S1 C1 1.8473(16) . ?
F6 C17 1.331(2) . ?
F8 C17 1.346(2) . ?
F7 C17 1.345(2) . ?
C1 C2 1.418(2) . ?
C1 C16 1.424(2) . ?
C5 C6 1.396(2) . ?
C5 C14 1.422(2) . ?
C5 C4 1.489(2) . ?
C18 C3 1.515(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C16 1.517(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C15 C16 1.402(2) . ?
C15 C4 1.425(2) . ?
C15 C13 1.4833(19) . ?
C17 C2 1.540(2) . ?
C8 C7 1.365(3) . ?
C8 C9 1.415(2) . ?
C8 H8 0.9500 . ?
C3 C4 1.398(2) . ?
C3 C2 1.420(2) . ?
C9 C14 1.402(2) . ?
C9 C10 1.414(2) . ?
C20 C12 1.505(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 C6 1.506(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C12 C13 1.389(2) . ?
C12 C11 1.430(2) . ?
C11 C10 1.367(2) . ?
C11 H11 0.9500 . ?
C14 C13 1.422(2) . ?
C10 H10 0.9500 . ?
C6 C7 1.431(2) . ?
C7 H7 0.9500 . ?

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
F2 S1 F1 91.68(7) . . ?
F2 S1 F3 88.60(7) . . ?
F1 S1 F3 173.86(6) . . ?
F2 S1 F4 174.32(7) . . ?
F1 S1 F4 88.76(7) . . ?
F3 S1 F4 90.36(7) . . ?
F2 S1 F5 87.58(8) . . ?
F1 S1 F5 86.91(8) . . ?
F3 S1 F5 86.97(8) . . ?
F4 S1 F5 86.78(8) . . ?
F2 S1 C1 92.73(7) . . ?
F1 S1 C1 93.43(7) . . ?
F3 S1 C1 92.68(7) . . ?
F4 S1 C1 92.90(7) . . ?
F5 S1 C1 179.53(8) . . ?
C2 C1 C16 120.56(13) . . ?
C2 C1 S1 122.46(11) . . ?
C16 C1 S1 116.94(11) . . ?
C6 C5 C14 117.55(14) . . ?
C6 C5 C4 136.55(14) . . ?
C14 C5 C4 105.41(12) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C15 C4 121.20(13) . . ?
C16 C15 C13 129.58(13) . . ?
C4 C15 C13 108.29(12) . . ?
F6 C17 F7 107.53(14) . . ?
F6 C17 F8 103.45(14) . . ?
F7 C17 F8 106.42(14) . . ?
F6 C17 C2 116.38(14) . . ?
F7 C17 C2 111.98(13) . . ?
F8 C17 C2 110.31(13) . . ?
C7 C8 C9 119.02(15) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C4 C3 C2 117.90(14) . . ?
C4 C3 C18 119.48(14) . . ?
C2 C3 C18 122.26(13) . . ?
C14 C9 C10 116.73(14) . . ?
C14 C9 C8 116.77(15) . . ?
C10 C9 C8 126.37(15) . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C4 C15 119.71(13) . . ?
C3 C4 C5 131.48(14) . . ?
C15 C4 C5 108.26(12) . . ?
C13 C12 C11 116.85(14) . . ?
C13 C12 C20 126.54(13) . . ?
C11 C12 C20 116.43(14) . . ?
C10 C11 C12 123.84(15) . . ?
C10 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C9 C14 C5 124.18(14) . . ?
C9 C14 C13 123.41(14) . . ?
C5 C14 C13 111.95(13) . . ?
C15 C16 C1 116.45(13) . . ?
C15 C16 C21 116.75(13) . . ?
C1 C16 C21 126.12(13) . . ?
C11 C10 C9 119.67(14) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C5 C6 C7 117.07(15) . . ?
C5 C6 C19 126.84(14) . . ?
C7 C6 C19 115.83(14) . . ?
C12 C13 C14 118.56(13) . . ?
C12 C13 C15 135.27(13) . . ?
C14 C13 C15 105.53(13) . . ?
C8 C7 C6 124.29(15) . . ?
C8 C7 H7 117.9 . . ?
C6 C7 H7 117.9 . . ?
C1 C2 C3 119.64(13) . . ?
C1 C2 C17 127.31(14) . . ?
C3 C2 C17 113.02(14) . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.091

_shelxl_version_number           2012-9

