# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1046444'
_audit_update_record             
;
2015-01-30 deposited with the CCDC.
2015-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 F3 O S'
_chemical_formula_weight         332.33

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   P21

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

_cell_length_a                   5.59300(10)
_cell_length_b                   8.1070(3)
_cell_length_c                   17.5700(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.029(2)
_cell_angle_gamma                90.00
_cell_volume                     793.60(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(1)
_cell_measurement_reflns_used    150
_cell_measurement_theta_min      12
_cell_measurement_theta_max      20

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(1)
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7127
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3610
_reflns_number_gt                2709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'HKL DENZO'
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1726P)²+0.1097P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(15)
_refine_ls_number_reflns         3610
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2313
_refine_ls_wR_factor_gt          0.1968
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.005

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
S S 0.5324(2) 0.33997(18) 0.04383(7) 0.0687(5) Uani 1 1 d . . .
C1 C -0.6886(6) 0.7013(5) -0.29621(19) 0.0470(7) Uani 1 1 d . . .
C2 C -0.7052(5) 0.8850(4) -0.28136(17) 0.0421(7) Uani 1 1 d . . .
C3 C -0.5352(7) 0.9942(5) -0.3054(2) 0.0536(9) Uani 1 1 d . . .
H3 H -0.4090 0.9548 -0.3314 0.064 Uiso 1 1 calc R . .
C4 C -0.5530(7) 1.1595(5) -0.2908(2) 0.0568(9) Uani 1 1 d . . .
H4 H -0.4402 1.2320 -0.3078 0.068 Uiso 1 1 calc R . .
C5 C -0.7364(8) 1.2195(5) -0.2513(2) 0.0594(9) Uani 1 1 d . . .
H5 H -0.7465 1.3319 -0.2416 0.071 Uiso 1 1 calc R . .
C6 C -0.9039(8) 1.1143(5) -0.2261(3) 0.0596(9) Uani 1 1 d . . .
H6 H -1.0270 1.1542 -0.1989 0.072 Uiso 1 1 calc R . .
C7 C -0.8873(7) 0.9475(5) -0.2419(2) 0.0530(9) Uani 1 1 d . . .
H7 H -1.0019 0.8758 -0.2254 0.064 Uiso 1 1 calc R . .
C8 C -0.4872(7) 0.6326(4) -0.2471(2) 0.0502(8) Uani 1 1 d . . .
C9 C -0.3248(7) 0.5836(5) -0.2030(2) 0.0507(8) Uani 1 1 d . . .
C10 C -0.1475(7) 0.5301(5) -0.1502(2) 0.0520(8) Uani 1 1 d . . .
C11 C 0.0029(7) 0.4928(5) -0.1005(2) 0.0519(8) Uani 1 1 d . . .
C12 C 0.1709(6) 0.4543(5) -0.0377(2) 0.0494(8) Uani 1 1 d . . .
C13 C 0.1504(8) 0.5133(6) 0.0366(2) 0.0607(10) Uani 1 1 d . . .
C14 C 0.3481(6) 0.4595(4) 0.09252(17) 0.0427(7) Uani 1 1 d . . .
H14 H 0.3677 0.4859 0.1442 0.051 Uiso 1 1 calc R . .
C15 C 0.3709(8) 0.3583(6) -0.0409(3) 0.0597(9) Uani 1 1 d . . .
C16 C -0.6658(7) 0.6586(5) -0.3803(2) 0.0530(8) Uani 1 1 d . . .
C17 C -0.8823(7) 0.7097(6) -0.4304(2) 0.0580(9) Uani 1 1 d . . .
C18 C -0.8510(12) 0.7280(9) -0.5146(3) 0.0874(15) Uani 1 1 d . . .
O1 O -1.0756(6) 0.7342(6) -0.4089(2) 0.0845(11) Uani 1 1 d . . .
F1 F -1.0487(12) 0.7565(14) -0.5546(3) 0.216(5) Uani 1 1 d . . .
F2 F -0.7181(17) 0.8525(9) -0.5269(3) 0.192(3) Uani 1 1 d . . .
F3 F -0.7449(16) 0.6067(7) -0.5421(3) 0.170(3) Uani 1 1 d . . .
H1 H -0.850(6) 0.641(5) -0.277(2) 0.034(8) Uiso 1 1 d . . .
H13 H 0.052(10) 0.579(7) 0.050(3) 0.069(15) Uiso 1 1 d . . .
H16B H -0.689(9) 0.522(8) -0.388(3) 0.069(14) Uiso 1 1 d . . .
H15 H 0.435(8) 0.332(7) -0.078(3) 0.058(12) Uiso 1 1 d . . .
H16A H -0.522(10) 0.722(8) -0.397(3) 0.080(15) 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
S C15 1.680(4) . ?
S C14 1.699(4) . ?
C1 C8 1.467(5) . ?
C1 C2 1.516(5) . ?
C1 C16 1.534(5) . ?
C1 H1 1.11(4) . ?
C2 C7 1.378(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.370(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.209(5) . ?
C9 C10 1.368(5) . ?
C10 C11 1.197(5) . ?
C11 C12 1.420(5) . ?
C12 C15 1.368(6) . ?
C12 C13 1.404(6) . ?
C13 C14 1.479(5) . ?
C13 H13 0.82(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.80(5) . ?
C16 C17 1.491(5) . ?
C16 H16B 1.12(6) . ?
C16 H16A 1.02(6) . ?
C17 O1 1.193(5) . ?
C17 C18 1.512(7) . ?
C18 F3 1.267(8) . ?
C18 F1 1.278(7) . ?
C18 F2 1.283(9) . ?

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
C15 S C14 95.33(19) . . ?
C8 C1 C2 109.1(3) . . ?
C8 C1 C16 110.9(3) . . ?
C2 C1 C16 113.5(3) . . ?
C8 C1 H1 105.1(18) . . ?
C2 C1 H1 108.7(19) . . ?
C16 C1 H1 109.3(19) . . ?
C7 C2 C3 118.3(3) . . ?
C7 C2 C1 120.5(3) . . ?
C3 C2 C1 121.3(3) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 118.9(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 121.7(4) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C1 175.6(4) . . ?
C8 C9 C10 177.3(4) . . ?
C11 C10 C9 175.0(4) . . ?
C10 C11 C12 175.8(4) . . ?
C15 C12 C13 111.5(4) . . ?
C15 C12 C11 125.5(4) . . ?
C13 C12 C11 123.0(4) . . ?
C12 C13 C14 113.6(4) . . ?
C12 C13 H13 127(4) . . ?
C14 C13 H13 119(4) . . ?
C13 C14 S 106.5(3) . . ?
C13 C14 H14 126.7 . . ?
S C14 H14 126.7 . . ?
C12 C15 S 113.0(3) . . ?
C12 C15 H15 128(3) . . ?
S C15 H15 117(3) . . ?
C17 C16 C1 112.0(3) . . ?
C17 C16 H16B 97(3) . . ?
C1 C16 H16B 109(3) . . ?
C17 C16 H16A 108(3) . . ?
C1 C16 H16A 108(3) . . ?
H16B C16 H16A 123(4) . . ?
O1 C17 C16 124.8(4) . . ?
O1 C17 C18 118.6(4) . . ?
C16 C17 C18 116.5(4) . . ?
F3 C18 F1 110.0(6) . . ?
F3 C18 F2 104.4(7) . . ?
F1 C18 F2 104.6(7) . . ?
F3 C18 C17 113.3(5) . . ?
F1 C18 C17 112.8(6) . . ?
F2 C18 C17 111.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.079
