# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_D
_database_code_depnum_ccdc_archive 'CCDC 1479295'
_audit_update_record             
;
2016-05-11 deposited with the CCDC.
2017-01-03 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         'C16 H16 F3 N O2 S'
_chemical_formula_sum            'C16 H16 F3 N O2 S'
_chemical_formula_weight         343.36

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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.5653(13)
_cell_length_b                   10.5123(16)
_cell_length_c                   17.819(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.319(3)
_cell_angle_gamma                90
_cell_volume                     1599.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3136
_cell_measurement_theta_min      0.995
_cell_measurement_theta_max      26.037

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9833
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         26.037
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3136
_reflns_number_gt                2369
_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       'CrysAlis (Oxford Diffraction,2006)'
_computing_cell_refinement       CrysAlis
_computing_data_reduction        CrysAlis
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0885P)²+2.0094P] 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         3136
_refine_ls_number_parameters     208
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1618
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.022
_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 0.84141(9) 0.96957(8) 0.23235(4) 0.0326(3) Uani 1 1 d . . . . .
O1 O 0.7043(3) 1.0409(2) 0.24563(13) 0.0434(6) Uani 1 1 d . . . . .
N1 N 0.8009(3) 0.8860(2) 0.15672(14) 0.0315(6) Uani 1 1 d . . . . .
O2 O 0.9075(3) 0.8834(2) 0.28841(13) 0.0456(6) Uani 1 1 d . . . . .
C12 C 0.9894(4) 1.0790(3) 0.21203(16) 0.0315(7) Uani 1 1 d . . . . .
C5 C 0.5781(3) 0.8515(3) 0.06667(16) 0.0303(7) Uani 1 1 d . . . . .
C8 C 0.7067(3) 0.9453(3) 0.09225(16) 0.0298(7) Uani 1 1 d . . . . .
H8A H 0.6557 1.0207 0.1116 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3612(4) 0.7235(3) 0.10060(18) 0.0412(8) Uani 1 1 d . . . . .
H7A H 0.2942 0.6974 0.1363 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4763(4) 0.8108(3) 0.11930(17) 0.0369(8) Uani 1 1 d . . . . .
H6A H 0.4867 0.8436 0.1679 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3447(4) 0.6738(3) 0.02797(18) 0.0361(7) Uani 1 1 d . . . . .
C13 C 0.9505(4) 1.2024(3) 0.19083(19) 0.0388(8) Uani 1 1 d . . . . .
H13A H 0.8469 1.2296 0.1888 0.047 Uiso 1 1 calc R U . . .
C15 C 1.2214(5) 1.2447(4) 0.1759(2) 0.0493(10) Uani 1 1 d . . . . .
H15A H 1.2993 1.3008 0.1633 0.059 Uiso 1 1 calc R U . . .
C11 C 1.1446(4) 1.0381(3) 0.21539(18) 0.0383(8) Uani 1 1 d . . . . .
H11A H 1.1698 0.9550 0.2296 0.046 Uiso 1 1 calc R U . . .
F1 F 0.0796(3) 0.6301(3) 0.0061(2) 0.1085(13) Uani 1 1 d . U . . .
F2 F 0.2243(4) 0.5262(3) -0.05775(19) 0.1020(12) Uani 1 1 d . U . . .
C4 C 0.5579(4) 0.8032(3) -0.00577(18) 0.0394(8) Uani 1 1 d . . . . .
H4A H 0.6231 0.8308 -0.0419 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4427(4) 0.7149(3) -0.02514(19) 0.0409(8) Uani 1 1 d . . . . .
H3A H 0.4310 0.6831 -0.0739 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8072(4) 0.9896(4) 0.03025(19) 0.0435(9) Uani 1 1 d . . . . .
H9A H 0.7415 1.0270 -0.0099 0.065 Uiso 1 1 calc R U . . .
H9B H 0.8815 1.0516 0.0502 0.065 Uiso 1 1 calc R U . . .
H9C H 0.8620 0.9182 0.0113 0.065 Uiso 1 1 calc R U . . .
C14 C 1.0681(5) 1.2848(3) 0.1728(2) 0.0473(9) Uani 1 1 d . . . . .
H14A H 1.0433 1.3679 0.1585 0.057 Uiso 1 1 calc R U . . .
F3 F 0.2202(5) 0.4850(4) 0.0551(2) 0.1421(18) Uani 1 1 d . U . . .
C16 C 1.2605(4) 1.1214(4) 0.19747(19) 0.0449(9) Uani 1 1 d . . . . .
H16A H 1.3644 1.0950 0.1999 0.054 Uiso 1 1 calc R U . . .
C1 C 0.2187(4) 0.5788(4) 0.0089(2) 0.0485(9) Uani 1 1 d . . . . .
C10 C 0.9068(4) 0.7826(3) 0.1393(2) 0.0448(9) Uani 1 1 d . . . . .
H10A H 0.9607 0.7522 0.1851 0.067 Uiso 1 1 calc R U . . .
H10B H 0.8475 0.7144 0.1154 0.067 Uiso 1 1 calc R U . . .
H10C H 0.9816 0.8133 0.1062 0.067 Uiso 1 1 calc R U . . .


_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 O1 1.428(2) . ?
S1 O2 1.433(2) . ?
S1 N1 1.624(3) . ?
S1 C12 1.769(3) . ?
N1 C10 1.463(4) . ?
N1 C8 1.490(4) . ?
C12 C13 1.385(5) . ?
C12 C11 1.394(5) . ?
C5 C4 1.386(4) . ?
C5 C6 1.395(4) . ?
C5 C8 1.523(4) . ?
C8 C9 1.524(4) . ?
C7 C6 1.369(5) . ?
C7 C2 1.393(5) . ?
C2 C3 1.381(5) . ?
C2 C1 1.490(5) . ?
C13 C14 1.384(5) . ?
C15 C14 1.376(6) . ?
C15 C16 1.386(5) . ?
C11 C16 1.380(5) . ?
F1 C1 1.306(5) . ?
F2 C1 1.314(5) . ?
C4 C3 1.380(5) . ?
F3 C1 1.284(5) . ?

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
O1 S1 O2 120.21(15) . . ?
O1 S1 N1 107.16(13) . . ?
O2 S1 N1 106.55(14) . . ?
O1 S1 C12 107.65(15) . . ?
O2 S1 C12 107.57(14) . . ?
N1 S1 C12 107.07(14) . . ?
C10 N1 C8 117.1(3) . . ?
C10 N1 S1 118.7(2) . . ?
C8 N1 S1 118.8(2) . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 S1 120.2(3) . . ?
C11 C12 S1 119.1(2) . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 C8 123.6(3) . . ?
C6 C5 C8 118.2(3) . . ?
N1 C8 C5 107.3(2) . . ?
N1 C8 C9 112.6(3) . . ?
C5 C8 C9 114.6(3) . . ?
C6 C7 C2 119.9(3) . . ?
C7 C6 C5 121.1(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 121.3(3) . . ?
C7 C2 C1 119.0(3) . . ?
C14 C13 C12 119.0(3) . . ?
C14 C15 C16 120.5(3) . . ?
C16 C11 C12 119.6(3) . . ?
C3 C4 C5 121.1(3) . . ?
C4 C3 C2 120.0(3) . . ?
C15 C14 C13 120.5(3) . . ?
C11 C16 C15 119.7(3) . . ?
F3 C1 F1 107.8(4) . . ?
F3 C1 F2 104.9(4) . . ?
F1 C1 F2 103.5(3) . . ?
F3 C1 C2 113.3(3) . . ?
F1 C1 C2 112.0(3) . . ?
F2 C1 C2 114.4(3) . . ?

_refine_diff_density_max         0.947
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.068



