# Electronic Supplementary Material (ESI) for ChemComm.
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1503839'
_audit_update_record             
;
2016-09-11 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 F3 O3 S'
_chemical_formula_weight         318.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.8802(4)
_cell_length_b                   10.6122(4)
_cell_length_c                   13.9723(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1465.01(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8280
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_process_details   sadabs

_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  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17085
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2583
_reflns_number_gt                2408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0804P)²+0.3402P] 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   0.04(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2583
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.73665(8) 0.01510(7) 0.41604(5) 0.0597(2) Uani 1 1 d . . .
F1 F 0.4936(3) -0.3657(4) 0.7384(2) 0.1332(12) Uani 1 1 d . . .
F2 F 0.6796(3) -0.3219(3) 0.81016(16) 0.1086(9) Uani 1 1 d . . .
F3 F 0.5765(5) -0.1790(3) 0.7324(2) 0.1687(18) Uani 1 1 d . . .
O1 O 0.5149(3) -0.5735(2) 0.38678(17) 0.0797(8) Uani 1 1 d . . .
O2 O 0.4619(2) -0.3692(2) 0.37620(17) 0.0684(6) Uani 1 1 d . . .
O3 O 0.7720(2) -0.25887(18) 0.43519(16) 0.0596(5) Uani 1 1 d . . .
C1 C 0.6863(3) -0.3332(3) 0.6436(2) 0.0521(6) Uani 1 1 d . . .
H1A H 0.7696 -0.2832 0.6416 0.062 Uiso 1 1 calc R . .
C2 C 0.7226(4) -0.4746(3) 0.6445(3) 0.0813(10) Uani 1 1 d . . .
H2A H 0.8197 -0.4867 0.6402 0.098 Uiso 1 1 calc R . .
H2B H 0.6897 -0.5149 0.7023 0.098 Uiso 1 1 calc R . .
C3 C 0.6526(4) -0.5259(3) 0.5578(3) 0.0688(8) Uani 1 1 d . . .
H3A H 0.6526 -0.6109 0.5415 0.083 Uiso 1 1 calc R . .
C4 C 0.5915(3) -0.4390(2) 0.5072(2) 0.0469(6) Uani 1 1 d . . .
C5 C 0.6029(2) -0.3096(2) 0.55020(18) 0.0432(5) Uani 1 1 d . . .
H5A H 0.5132 -0.2758 0.5655 0.052 Uiso 1 1 calc R . .
C6 C 0.6792(2) -0.2204(2) 0.48385(19) 0.0432(6) Uani 1 1 d . . .
C7 C 0.6391(3) -0.0879(2) 0.48193(19) 0.0481(6) Uani 1 1 d . . .
C8 C 0.6325(4) 0.1361(3) 0.4435(2) 0.0670(8) Uani 1 1 d . . .
H8A H 0.6455 0.2180 0.4215 0.080 Uiso 1 1 calc R . .
C9 C 0.5294(4) 0.1023(3) 0.5001(3) 0.0712(9) Uani 1 1 d . . .
H9A H 0.4639 0.1584 0.5218 0.085 Uiso 1 1 calc R . .
C10 C 0.5301(3) -0.0272(3) 0.5238(2) 0.0593(7) Uani 1 1 d . . .
H10A H 0.4659 -0.0664 0.5624 0.071 Uiso 1 1 calc R . .
C11 C 0.6086(4) -0.3000(4) 0.7305(3) 0.0807(10) Uani 1 1 d . . .
C12 C 0.5156(3) -0.4551(3) 0.4168(2) 0.0510(6) Uani 1 1 d . . .
C13 C 0.4447(5) -0.6016(5) 0.2975(3) 0.1014(15) Uani 1 1 d . . .
H13A H 0.4190 -0.5232 0.2667 0.122 Uiso 1 1 calc R . .
H13B H 0.5057 -0.6461 0.2549 0.122 Uiso 1 1 calc R . .
C14 C 0.3319(5) -0.6729(6) 0.3122(4) 0.133(2) Uani 1 1 d . . .
H14A H 0.2897 -0.6910 0.2518 0.199 Uiso 1 1 calc R . .
H14B H 0.2697 -0.6276 0.3522 0.199 Uiso 1 1 calc R . .
H14C H 0.3568 -0.7504 0.3429 0.199 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 C8 1.690(3) . ?
S1 C7 1.724(3) . ?
F1 C11 1.337(5) . ?
F2 C11 1.335(4) . ?
F3 C11 1.323(5) . ?
O1 C12 1.325(4) . ?
O1 C13 1.458(4) . ?
O2 C12 1.197(4) . ?
O3 C6 1.212(3) . ?
C1 C11 1.479(5) . ?
C1 C2 1.543(4) . ?
C1 C5 1.564(4) . ?
C1 H1A 0.9800 . ?
C2 C3 1.498(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.309(4) . ?
C3 H3A 0.9300 . ?
C4 C12 1.479(4) . ?
C4 C5 1.504(3) . ?
C5 C6 1.524(4) . ?
C5 H5A 0.9800 . ?
C6 C7 1.461(3) . ?
C7 C10 1.385(4) . ?
C8 C9 1.339(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.413(4) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C13 C14 1.363(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C7 91.16(14) . . ?
C12 O1 C13 117.8(3) . . ?
C11 C1 C2 110.2(3) . . ?
C11 C1 C5 111.9(2) . . ?
C2 C1 C5 106.5(2) . . ?
C11 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C5 C1 H1A 109.4 . . ?
C3 C2 C1 103.9(2) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 113.2(3) . . ?
C4 C3 H3A 123.4 . . ?
C2 C3 H3A 123.4 . . ?
C3 C4 C12 127.8(3) . . ?
C3 C4 C5 113.2(2) . . ?
C12 C4 C5 119.0(2) . . ?
C4 C5 C6 111.2(2) . . ?
C4 C5 C1 103.1(2) . . ?
C6 C5 C1 110.3(2) . . ?
C4 C5 H5A 110.7 . . ?
C6 C5 H5A 110.7 . . ?
C1 C5 H5A 110.7 . . ?
O3 C6 C7 121.3(2) . . ?
O3 C6 C5 120.4(2) . . ?
C7 C6 C5 118.3(2) . . ?
C10 C7 C6 130.6(3) . . ?
C10 C7 S1 111.5(2) . . ?
C6 C7 S1 117.9(2) . . ?
C9 C8 S1 113.2(2) . . ?
C9 C8 H8A 123.4 . . ?
S1 C8 H8A 123.4 . . ?
C8 C9 C10 113.3(3) . . ?
C8 C9 H9A 123.3 . . ?
C10 C9 H9A 123.3 . . ?
C7 C10 C9 110.9(3) . . ?
C7 C10 H10A 124.6 . . ?
C9 C10 H10A 124.6 . . ?
F3 C11 F2 106.2(3) . . ?
F3 C11 F1 107.5(4) . . ?
F2 C11 F1 106.7(3) . . ?
F3 C11 C1 111.8(4) . . ?
F2 C11 C1 111.7(3) . . ?
F1 C11 C1 112.6(3) . . ?
O2 C12 O1 124.7(3) . . ?
O2 C12 C4 122.8(3) . . ?
O1 C12 C4 112.5(2) . . ?
C14 C13 O1 111.9(4) . . ?
C14 C13 H13A 109.2 . . ?
O1 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
O1 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C11 C1 C2 C3 118.0(3) . . . . ?
C5 C1 C2 C3 -3.6(4) . . . . ?
C1 C2 C3 C4 3.4(4) . . . . ?
C2 C3 C4 C12 178.6(3) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C3 C4 C5 C6 117.4(3) . . . . ?
C12 C4 C5 C6 -62.8(3) . . . . ?
C3 C4 C5 C1 -0.7(3) . . . . ?
C12 C4 C5 C1 179.0(2) . . . . ?
C11 C1 C5 C4 -117.8(3) . . . . ?
C2 C1 C5 C4 2.7(3) . . . . ?
C11 C1 C5 C6 123.4(3) . . . . ?
C2 C1 C5 C6 -116.1(3) . . . . ?
C4 C5 C6 O3 -35.1(3) . . . . ?
C1 C5 C6 O3 78.6(3) . . . . ?
C4 C5 C6 C7 146.0(2) . . . . ?
C1 C5 C6 C7 -100.3(3) . . . . ?
O3 C6 C7 C10 173.0(3) . . . . ?
C5 C6 C7 C10 -8.0(4) . . . . ?
O3 C6 C7 S1 -5.3(3) . . . . ?
C5 C6 C7 S1 173.58(18) . . . . ?
C8 S1 C7 C10 -0.4(2) . . . . ?
C8 S1 C7 C6 178.3(2) . . . . ?
C7 S1 C8 C9 0.5(3) . . . . ?
S1 C8 C9 C10 -0.4(4) . . . . ?
C6 C7 C10 C9 -178.2(3) . . . . ?
S1 C7 C10 C9 0.3(3) . . . . ?
C8 C9 C10 C7 0.1(5) . . . . ?
C2 C1 C11 F3 179.6(4) . . . . ?
C5 C1 C11 F3 -62.0(4) . . . . ?
C2 C1 C11 F2 60.8(4) . . . . ?
C5 C1 C11 F2 179.2(3) . . . . ?
C2 C1 C11 F1 -59.2(4) . . . . ?
C5 C1 C11 F1 59.2(4) . . . . ?
C13 O1 C12 O2 0.5(5) . . . . ?
C13 O1 C12 C4 -179.2(3) . . . . ?
C3 C4 C12 O2 179.3(3) . . . . ?
C5 C4 C12 O2 -0.4(4) . . . . ?
C3 C4 C12 O1 -0.9(4) . . . . ?
C5 C4 C12 O1 179.4(3) . . . . ?
C12 O1 C13 C14 -112.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.044
