# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_hpsolve
_database_code_depnum_ccdc_archive 'CCDC 1538643'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H7 F3 N2 O S'
_chemical_formula_weight         320.29

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9423(11)
_cell_length_b                   8.3974(10)
_cell_length_c                   11.4457(16)
_cell_angle_alpha                99.623(9)
_cell_angle_beta                 101.966(9)
_cell_angle_gamma                98.974(9)
_cell_volume                     721.75(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2379
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.04

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.084
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_max          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4263
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2505
_reflns_number_gt                1730
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2σ(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)+(0.0251P)²+0.4155P] 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     SHELXL
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2505
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.031
_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
C16 C 0.0800(4) 0.0966(4) 0.8527(3) 0.0681(9) Uani 1 1 d . . .
F7 F -0.0662(2) -0.0016(3) 0.8553(2) 0.0957(7) Uani 1 1 d . . .
F5 F 0.0580(3) 0.1265(3) 0.7422(2) 0.1031(8) Uani 1 1 d . . .
F6 F 0.0895(3) 0.2376(3) 0.9260(2) 0.1084(8) Uani 1 1 d . . .
H10 H 0.558(4) 0.551(4) 0.724(3) 0.072(9) Uiso 1 1 d . . .
H3 H 0.635(4) 0.203(4) 0.664(3) 0.083(11) Uiso 1 1 d . . .
H9 H 0.521(5) 0.723(4) 0.578(3) 0.090(11) Uiso 1 1 d . . .
H5 H 0.731(4) 0.468(4) 0.999(3) 0.073(10) Uiso 1 1 d . . .
H6 H 0.504(4) 0.283(4) 1.034(3) 0.067(9) Uiso 1 1 d . . .
H8 H 0.753(4) 0.820(4) 0.502(3) 0.076(10) Uiso 1 1 d . . .
H2 H 0.411(5) 0.020(4) 0.703(3) 0.091(12) Uiso 1 1 d . . .
S1 S 0.25858(11) -0.00138(10) 0.89496(9) 0.0732(3) Uani 1 1 d . . .
O1 O 0.8417(2) 0.4536(3) 0.8079(2) 0.0720(6) Uani 1 1 d . . .
C12 C 0.9488(3) 0.6054(3) 0.6773(3) 0.0495(7) Uani 1 1 d . . .
C5 C 0.6624(4) 0.3756(4) 0.9380(3) 0.0570(8) Uani 1 1 d . . .
C4 C 0.6991(4) 0.3486(4) 0.8264(3) 0.0583(8) Uani 1 1 d . . .
C7 C 0.8083(3) 0.5480(3) 0.7238(3) 0.0552(7) Uani 1 1 d . . .
C11 C 0.9264(4) 0.7081(3) 0.5933(3) 0.0548(7) Uani 1 1 d . . .
C13 C 1.0726(4) 0.7673(4) 0.5459(3) 0.0629(8) Uani 1 1 d . . .
C14 C 1.1140(4) 0.5579(3) 0.7141(3) 0.0554(7) Uani 1 1 d . . .
C6 C 0.5252(4) 0.2692(4) 0.9584(3) 0.0571(8) Uani 1 1 d . . .
C1 C 0.4300(4) 0.1388(3) 0.8678(3) 0.0540(7) Uani 1 1 d . . .
C9 C 0.6291(5) 0.6928(4) 0.6036(4) 0.0768(10) Uani 1 1 d . . .
C8 C 0.6481(4) 0.5929(4) 0.6860(3) 0.0660(9) Uani 1 1 d . . .
C3 C 0.6097(5) 0.2177(5) 0.7361(4) 0.0744(10) Uani 1 1 d . . .
N2 N 1.1903(4) 0.8132(4) 0.5103(3) 0.0819(9) Uani 1 1 d . . .
C2 C 0.4729(4) 0.1122(5) 0.7568(3) 0.0708(9) Uani 1 1 d . . .
C10 C 0.7664(4) 0.7521(4) 0.5561(4) 0.0730(10) Uani 1 1 d . . .
N1 N 1.2463(3) 0.5208(4) 0.7413(3) 0.0766(8) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C16 F6 1.313(4) . ?
C16 F5 1.313(4) . ?
C16 F7 1.323(3) . ?
C16 S1 1.771(3) . ?
S1 C1 1.770(3) . ?
O1 C7 1.356(3) . ?
O1 C4 1.399(3) . ?
C12 C7 1.388(4) . ?
C12 C11 1.397(4) . ?
C12 C14 1.431(4) . ?
C5 C4 1.359(4) . ?
C5 C6 1.382(4) . ?
C5 H5 0.96(3) . ?
C4 C3 1.361(5) . ?
C7 C8 1.387(4) . ?
C11 C10 1.381(4) . ?
C11 C13 1.436(4) . ?
C13 N2 1.134(4) . ?
C14 N1 1.139(3) . ?
C6 C1 1.372(4) . ?
C6 H6 0.91(3) . ?
C1 C2 1.374(4) . ?
C9 C8 1.365(5) . ?
C9 C10 1.378(5) . ?
C9 H9 0.93(3) . ?
C8 H10 0.96(3) . ?
C3 C2 1.378(5) . ?
C3 H3 0.89(3) . ?
C2 H2 0.91(4) . ?
C10 H8 0.91(3) . ?

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
F6 C16 F5 106.2(3) . . ?
F6 C16 F7 106.9(3) . . ?
F5 C16 F7 106.6(3) . . ?
F6 C16 S1 114.1(2) . . ?
F5 C16 S1 114.1(3) . . ?
F7 C16 S1 108.5(2) . . ?
C1 S1 C16 99.99(14) . . ?
C7 O1 C4 117.7(2) . . ?
C7 C12 C11 119.3(3) . . ?
C7 C12 C14 120.1(3) . . ?
C11 C12 C14 120.6(3) . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 118.8(19) . . ?
C6 C5 H5 122.7(18) . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 O1 118.1(3) . . ?
C3 C4 O1 119.5(3) . . ?
O1 C7 C8 124.5(3) . . ?
O1 C7 C12 115.9(2) . . ?
C8 C7 C12 119.5(3) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 C13 120.3(3) . . ?
C12 C11 C13 118.9(3) . . ?
N2 C13 C11 178.6(4) . . ?
N1 C14 C12 178.6(3) . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 120.7(19) . . ?
C5 C6 H6 118.8(19) . . ?
C6 C1 C2 119.8(3) . . ?
C6 C1 S1 120.5(2) . . ?
C2 C1 S1 119.6(2) . . ?
C8 C9 C10 121.6(3) . . ?
C8 C9 H9 120(2) . . ?
C10 C9 H9 118(2) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H10 125.1(18) . . ?
C7 C8 H10 114.8(19) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 121(2) . . ?
C2 C3 H3 120(2) . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 116(2) . . ?
C3 C2 H2 124(2) . . ?
C9 C10 C11 118.7(3) . . ?
C9 C10 H8 121(2) . . ?
C11 C10 H8 120(2) . . ?

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
F6 C16 S1 C1 -67.5(3) . . . . ?
F5 C16 S1 C1 54.9(3) . . . . ?
F7 C16 S1 C1 173.5(2) . . . . ?
C6 C5 C4 C3 -2.4(5) . . . . ?
C6 C5 C4 O1 -177.9(3) . . . . ?
C7 O1 C4 C5 -116.6(3) . . . . ?
C7 O1 C4 C3 67.7(4) . . . . ?
C4 O1 C7 C8 23.5(4) . . . . ?
C4 O1 C7 C12 -158.6(3) . . . . ?
C11 C12 C7 O1 -177.9(2) . . . . ?
C14 C12 C7 O1 3.0(4) . . . . ?
C11 C12 C7 C8 0.2(4) . . . . ?
C14 C12 C7 C8 -179.0(3) . . . . ?
C7 C12 C11 C10 -0.2(4) . . . . ?
C14 C12 C11 C10 179.0(3) . . . . ?
C7 C12 C11 C13 179.8(3) . . . . ?
C14 C12 C11 C13 -1.0(4) . . . . ?
C10 C11 C13 N2 164(15) . . . . ?
C12 C11 C13 N2 -16(15) . . . . ?
C7 C12 C14 N1 159(14) . . . . ?
C11 C12 C14 N1 -20(14) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C5 C6 C1 C2 1.0(4) . . . . ?
C5 C6 C1 S1 178.0(2) . . . . ?
C16 S1 C1 C6 89.6(3) . . . . ?
C16 S1 C1 C2 -93.3(3) . . . . ?
C10 C9 C8 C7 -0.2(6) . . . . ?
O1 C7 C8 C9 177.9(3) . . . . ?
C12 C7 C8 C9 0.1(5) . . . . ?
C5 C4 C3 C2 2.5(5) . . . . ?
O1 C4 C3 C2 178.0(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
S1 C1 C2 C3 -178.0(3) . . . . ?
C4 C3 C2 C1 -0.8(5) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C12 C11 C10 C9 0.0(5) . . . . ?
C13 C11 C10 C9 180.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.041
