# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_napotf-1
_database_code_depnum_ccdc_archive 'CCDC 1433323'
_audit_update_record             
;
2016-03-15 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 F3 O4 S'
_chemical_formula_sum            'C16 H13 F3 O4 S'
_chemical_formula_weight         358.32

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'
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/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8732(3)
_cell_length_b                   8.2240(4)
_cell_length_c                   33.7553(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.151(3)
_cell_angle_gamma                90.00
_cell_volume                     1626.14(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3286
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.59

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   multi-scan

_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            15811
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.21
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2923
_reflns_number_gt                1397
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0000P)²+7.0395P] 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_number_reflns         2923
_refine_ls_number_parameters     217
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.2197
_refine_ls_R_factor_gt           0.1452
_refine_ls_wR_factor_ref         0.2402
_refine_ls_wR_factor_gt          0.2008
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.252
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003

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 0.4301(12) 0.7005(7) 0.04537(19) 0.202(2) Uani 1 1 d D . .
C8 C 0.3969(15) 0.3418(10) 0.2506(3) 0.080(2) Uani 1 1 d . . .
C13 C 0.5951(15) 0.2563(11) 0.2422(3) 0.081(3) Uani 1 1 d . . .
C6 C 0.2758(14) 0.3372(11) 0.1801(3) 0.081(3) Uani 1 1 d . . .
C7 C 0.2386(16) 0.3816(10) 0.2181(3) 0.087(3) Uani 1 1 d . . .
H7 H 0.1070 0.4392 0.2228 0.105 Uiso 1 1 calc R . .
C14 C 0.6333(16) 0.2140(12) 0.2038(4) 0.099(3) Uani 1 1 d . . .
H14 H 0.7666 0.1592 0.1987 0.119 Uiso 1 1 calc R . .
C12 C 0.7544(19) 0.2156(12) 0.2748(4) 0.115(4) Uani 1 1 d . . .
H12 H 0.8843 0.1562 0.2699 0.138 Uiso 1 1 calc R . .
C9 C 0.3619(17) 0.3859(13) 0.2887(4) 0.098(3) Uani 1 1 d . . .
H9 H 0.2294 0.4417 0.2938 0.118 Uiso 1 1 calc R . .
C15 C 0.4807(17) 0.2507(12) 0.1737(4) 0.103(3) Uani 1 1 d . . .
H15 H 0.5089 0.2192 0.1480 0.124 Uiso 1 1 calc R . .
C10 C 0.514(2) 0.3508(14) 0.3187(4) 0.115(4) Uani 1 1 d . . .
H10 H 0.4861 0.3845 0.3442 0.139 Uiso 1 1 calc R . .
C11 C 0.720(2) 0.2617(15) 0.3127(4) 0.126(4) Uani 1 1 d . . .
H11 H 0.8254 0.2369 0.3338 0.151 Uiso 1 1 calc R . .
C4 C 0.201(2) 0.5148(14) 0.1221(4) 0.133(5) Uani 1 1 d . . .
H4 H 0.2698 0.6055 0.1343 0.160 Uiso 1 1 calc R . .
C5 C 0.1107(19) 0.3832(12) 0.1472(3) 0.103(3) Uani 1 1 d . . .
H5 H -0.0301 0.4210 0.1581 0.123 Uiso 1 1 calc R . .
O1 O 0.0617(13) 0.2425(9) 0.1239(2) 0.117(2) Uani 1 1 d . . .
C3 C 0.184(3) 0.5046(18) 0.0844(5) 0.173(7) Uani 1 1 d . . .
C17 C 0.068(3) 0.3706(19) 0.0597(4) 0.161(5) Uani 1 1 d . . .
H17A H -0.0293 0.4164 0.0381 0.193 Uiso 1 1 calc R . .
H17B H 0.1812 0.3016 0.0486 0.193 Uiso 1 1 calc R . .
C16 C -0.071(2) 0.2749(16) 0.0868(4) 0.144(5) Uani 1 1 d . . .
H16A H -0.2071 0.3352 0.0920 0.172 Uiso 1 1 calc R . .
H16B H -0.1171 0.1730 0.0742 0.172 Uiso 1 1 calc R . .
O2 O 0.207(3) 0.645(2) 0.0544(5) 0.306(9) Uani 1 1 d . . .
O3 O 0.581(4) 0.633(3) 0.0795(6) 0.395(15) Uani 1 1 d . . .
O4 O 0.493(3) 0.7214(16) 0.0079(3) 0.270(7) Uani 1 1 d . . .
F1 F 0.337(3) 0.8880(14) 0.0996(4) 0.336(9) Uani 1 1 d D . .
C1 C 0.395(3) 0.8626(15) 0.0634(5) 0.34(2) Uani 1 1 d D . .
F3 F 0.281(4) 0.968(2) 0.0401(6) 0.458(16) Uani 1 1 d D . .
F2 F 0.606(4) 0.934(3) 0.0618(8) 0.477(17) Uani 1 1 d 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 O4 1.353(9) . ?
S1 O2 1.442(13) . ?
S1 C1 1.485(8) . ?
S1 O3 1.507(18) . ?
C8 C9 1.365(12) . ?
C8 C13 1.406(11) . ?
C8 C7 1.425(12) . ?
C13 C14 1.377(12) . ?
C13 C12 1.431(13) . ?
C6 C7 1.366(12) . ?
C6 C15 1.428(12) . ?
C6 C5 1.471(13) . ?
C14 C15 1.340(13) . ?
C12 C11 1.365(15) . ?
C9 C10 1.333(13) . ?
C10 C11 1.442(15) . ?
C4 C3 1.273(17) . ?
C4 C5 1.493(13) . ?
C5 O1 1.417(11) . ?
O1 C16 1.448(12) . ?
C3 C17 1.512(18) . ?
C3 O2 1.547(19) . ?
C17 C16 1.493(15) . ?
F1 C1 1.311(10) . ?
C1 F3 1.321(17) . ?
C1 F2 1.371(7) . ?

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
O4 S1 O2 123.5(11) . . ?
O4 S1 C1 108.9(10) . . ?
O2 S1 C1 92.6(10) . . ?
O4 S1 O3 125.0(11) . . ?
O2 S1 O3 102.5(10) . . ?
C1 S1 O3 96.2(13) . . ?
C9 C8 C13 120.4(10) . . ?
C9 C8 C7 122.0(9) . . ?
C13 C8 C7 117.6(10) . . ?
C14 C13 C8 120.7(10) . . ?
C14 C13 C12 121.5(10) . . ?
C8 C13 C12 117.9(10) . . ?
C7 C6 C15 118.0(10) . . ?
C7 C6 C5 119.9(9) . . ?
C15 C6 C5 122.0(10) . . ?
C6 C7 C8 121.5(9) . . ?
C15 C14 C13 120.8(10) . . ?
C11 C12 C13 121.6(11) . . ?
C10 C9 C8 121.3(11) . . ?
C14 C15 C6 121.4(10) . . ?
C9 C10 C11 121.9(12) . . ?
C12 C11 C10 117.0(13) . . ?
C3 C4 C5 120.9(12) . . ?
O1 C5 C6 107.8(9) . . ?
O1 C5 C4 110.1(9) . . ?
C6 C5 C4 111.9(10) . . ?
C5 O1 C16 113.8(9) . . ?
C4 C3 C17 126.8(12) . . ?
C4 C3 O2 127.1(15) . . ?
C17 C3 O2 103.8(14) . . ?
C16 C17 C3 106.8(11) . . ?
O1 C16 C17 110.1(11) . . ?
S1 O2 C3 120.1(15) . . ?
F1 C1 F3 107.1(14) . . ?
F1 C1 F2 105.4(18) . . ?
F3 C1 F2 96.7(17) . . ?
F1 C1 S1 125.3(13) . . ?
F3 C1 S1 115.2(15) . . ?
F2 C1 S1 102.5(12) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.095


