# 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_bb
_database_code_depnum_ccdc_archive 'CCDC 1011275'
_audit_update_record             
;
2014-06-30 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C17 H14 F3 N3 S'
_chemical_formula_sum            'C17 H14 F3 N3 S'
_chemical_formula_weight         349.37

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'
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   P_b_c_a

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

_cell_length_a                   14.222(5)
_cell_length_b                   8.925(5)
_cell_length_c                   25.350(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3218(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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            19138
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3696
_reflns_number_gt                2618
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-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)+(0.0622P)²+0.9923P] 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_number_reflns         3696
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
C1 C 0.33051(15) 0.5557(2) 0.16317(8) 0.0489(5) Uani 1 1 d . . .
C2 C 0.32596(14) 0.4495(2) 0.20853(8) 0.0424(5) Uani 1 1 d . . .
C3 C 0.24191(14) 0.4206(2) 0.23385(8) 0.0450(5) Uani 1 1 d . . .
H3 H 0.1873 0.4683 0.2227 0.054 Uiso 1 1 calc R . .
C4 C 0.23847(14) 0.3211(2) 0.27561(8) 0.0441(5) Uani 1 1 d . . .
H4 H 0.1818 0.3011 0.2925 0.053 Uiso 1 1 calc R . .
C5 C 0.32024(13) 0.2517(2) 0.29194(8) 0.0390(4) Uani 1 1 d . . .
C6 C 0.40502(14) 0.2790(2) 0.26690(9) 0.0497(5) Uani 1 1 d . . .
H6 H 0.4596 0.2312 0.2781 0.060 Uiso 1 1 calc R . .
C7 C 0.40740(15) 0.3786(2) 0.22494(9) 0.0521(5) Uani 1 1 d . . .
H7 H 0.4639 0.3978 0.2078 0.063 Uiso 1 1 calc R . .
C8 C 0.35686(15) -0.0125(2) 0.38943(9) 0.0504(5) Uani 1 1 d . . .
H8 H 0.3913 -0.0807 0.4093 0.060 Uiso 1 1 calc R . .
C9 C 0.26181(14) 0.0204(2) 0.39657(8) 0.0422(5) Uani 1 1 d . . .
C10 C 0.10107(13) 0.0779(2) 0.45446(8) 0.0388(4) Uani 1 1 d . . .
C11 C 0.02257(14) 0.0951(2) 0.42162(8) 0.0444(5) Uani 1 1 d . . .
C12 C -0.04352(15) 0.2022(2) 0.43548(10) 0.0523(5) Uani 1 1 d . . .
H12 H -0.0961 0.2158 0.4142 0.063 Uiso 1 1 calc R . .
C13 C -0.03334(15) 0.2885(2) 0.47974(10) 0.0550(6) Uani 1 1 d . . .
H13 H -0.0787 0.3596 0.4883 0.066 Uiso 1 1 calc R . .
C14 C 0.04380(16) 0.2700(2) 0.51143(9) 0.0524(5) Uani 1 1 d . . .
H14 H 0.0503 0.3295 0.5413 0.063 Uiso 1 1 calc R . .
C15 C 0.11232(14) 0.1646(2) 0.49999(8) 0.0440(5) Uani 1 1 d . . .
C16 C 0.00889(19) 0.0036(3) 0.37274(10) 0.0724(7) Uani 1 1 d . . .
H16A H 0.0604 -0.0651 0.3689 0.109 Uiso 1 1 calc R . .
H16B H 0.0064 0.0686 0.3426 0.109 Uiso 1 1 calc R . .
H16C H -0.0489 -0.0515 0.3754 0.109 Uiso 1 1 calc R . .
C17 C 0.19520(17) 0.1471(3) 0.53627(11) 0.0681(7) Uani 1 1 d . . .
H17A H 0.1897 0.2165 0.5650 0.102 Uiso 1 1 calc R . .
H17B H 0.2521 0.1668 0.5171 0.102 Uiso 1 1 calc R . .
H17C H 0.1967 0.0466 0.5498 0.102 Uiso 1 1 calc R . .
N1 N 0.31666(10) 0.14926(18) 0.33475(6) 0.0404(4) Uani 1 1 d . . .
N2 N 0.39044(11) 0.0684(2) 0.34997(7) 0.0504(4) Uani 1 1 d . . .
N3 N 0.23664(11) 0.12357(18) 0.36142(7) 0.0431(4) Uani 1 1 d . . .
F1 F 0.24657(10) 0.61164(19) 0.14998(6) 0.0772(5) Uani 1 1 d . . .
F2 F 0.36614(15) 0.49453(18) 0.12017(6) 0.0945(6) Uani 1 1 d . . .
F3 F 0.38376(10) 0.67521(14) 0.17307(6) 0.0676(4) Uani 1 1 d . . .
S1 S 0.18450(4) -0.06673(6) 0.44086(3) 0.0576(2) 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
C1 F2 1.320(3) . ?
C1 F3 1.332(2) . ?
C1 F1 1.337(2) . ?
C1 C2 1.491(3) . ?
C2 C3 1.381(3) . ?
C2 C7 1.384(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 N1 1.420(2) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.323(3) . ?
C8 C9 1.395(3) . ?
C8 H8 0.9300 . ?
C9 N3 1.331(2) . ?
C9 S1 1.753(2) . ?
C10 C15 1.399(3) . ?
C10 C11 1.401(3) . ?
C10 S1 1.787(2) . ?
C11 C12 1.386(3) . ?
C11 C16 1.497(3) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.503(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 N2 1.331(2) . ?
N1 N3 1.343(2) . ?

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 C1 F3 105.56(19) . . ?
F2 C1 F1 106.90(19) . . ?
F3 C1 F1 104.80(17) . . ?
F2 C1 C2 113.00(18) . . ?
F3 C1 C2 112.84(18) . . ?
F1 C1 C2 113.06(18) . . ?
C3 C2 C7 119.93(19) . . ?
C3 C2 C1 120.98(18) . . ?
C7 C2 C1 119.09(18) . . ?
C2 C3 C4 120.44(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.19(18) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.15(19) . . ?
C4 C5 N1 119.18(17) . . ?
C6 C5 N1 119.67(17) . . ?
C5 C6 C7 119.06(19) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 120.23(19) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N2 C8 C9 109.46(18) . . ?
N2 C8 H8 125.3 . . ?
C9 C8 H8 125.3 . . ?
N3 C9 C8 108.62(17) . . ?
N3 C9 S1 124.55(15) . . ?
C8 C9 S1 126.69(16) . . ?
C15 C10 C11 121.38(18) . . ?
C15 C10 S1 118.87(15) . . ?
C11 C10 S1 119.59(16) . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 C16 119.9(2) . . ?
C10 C11 C16 122.4(2) . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 117.90(19) . . ?
C14 C15 C17 119.6(2) . . ?
C10 C15 C17 122.5(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 N1 N3 115.44(16) . . ?
N2 N1 C5 122.85(15) . . ?
N3 N1 C5 121.66(15) . . ?
C8 N2 N1 103.33(16) . . ?
C9 N3 N1 103.14(15) . . ?
C9 S1 C10 102.69(9) . . ?

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
F2 C1 C2 C3 -123.7(2) . . . . ?
F3 C1 C2 C3 116.7(2) . . . . ?
F1 C1 C2 C3 -2.1(3) . . . . ?
F2 C1 C2 C7 55.8(3) . . . . ?
F3 C1 C2 C7 -63.9(3) . . . . ?
F1 C1 C2 C7 177.40(19) . . . . ?
C7 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C4 179.52(18) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 N1 -179.86(17) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
N1 C5 C6 C7 179.61(19) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C1 C2 C7 C6 -179.77(19) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
N2 C8 C9 N3 -0.5(3) . . . . ?
N2 C8 C9 S1 175.37(16) . . . . ?
C15 C10 C11 C12 0.6(3) . . . . ?
S1 C10 C11 C12 175.94(15) . . . . ?
C15 C10 C11 C16 -179.9(2) . . . . ?
S1 C10 C11 C16 -4.6(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C16 C11 C12 C13 -179.7(2) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C13 C14 C15 C17 -179.3(2) . . . . ?
C11 C10 C15 C14 -0.8(3) . . . . ?
S1 C10 C15 C14 -176.19(15) . . . . ?
C11 C10 C15 C17 179.2(2) . . . . ?
S1 C10 C15 C17 3.8(3) . . . . ?
C4 C5 N1 N2 174.14(18) . . . . ?
C6 C5 N1 N2 -5.1(3) . . . . ?
C4 C5 N1 N3 -3.3(3) . . . . ?
C6 C5 N1 N3 177.52(19) . . . . ?
C9 C8 N2 N1 1.0(2) . . . . ?
N3 N1 N2 C8 -1.2(2) . . . . ?
C5 N1 N2 C8 -178.72(18) . . . . ?
C8 C9 N3 N1 -0.2(2) . . . . ?
S1 C9 N3 N1 -176.18(14) . . . . ?
N2 N1 N3 C9 0.9(2) . . . . ?
C5 N1 N3 C9 178.45(16) . . . . ?
N3 C9 S1 C10 -33.0(2) . . . . ?
C8 C9 S1 C10 151.76(19) . . . . ?
C15 C10 S1 C9 -97.07(16) . . . . ?
C11 C10 S1 C9 87.45(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.042
