# 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 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1504792'
_audit_update_record             
;
2016-09-18 deposited with the CCDC.
2017-06-26 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         ?
_chemical_formula_sum            'C12 H8 F3 N2 O2 S'
_chemical_formula_weight         301.26

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   5.8417(3)
_cell_length_b                   8.9060(5)
_cell_length_c                   12.8197(7)
_cell_angle_alpha                86.180(2)
_cell_angle_beta                 88.587(2)
_cell_angle_gamma                72.272(2)
_cell_volume                     633.87(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      28.3

_exptl_crystal_description       block
_exptl_crystal_colour            lightyellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             306
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.295
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30889
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3143
_reflns_number_gt                2875
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1098P)²+0.5789P] 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         3143
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.2019
_refine_ls_wR_factor_gt          0.1973
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.46752(10) 0.30331(7) 0.13851(5) 0.0397(2) Uani 1 1 d . . . . .
F1 F 0.2219(12) 0.3225(8) 0.6498(3) 0.206(3) Uani 1 1 d . . . . .
N1 N 0.2572(4) 0.4384(2) 0.08199(16) 0.0384(5) Uani 1 1 d . . . . .
F3 F -0.0396(7) 0.2482(10) 0.6026(3) 0.227(4) Uani 1 1 d . . . . .
F2 F 0.2875(12) 0.0990(6) 0.6306(3) 0.223(3) Uani 1 1 d . . . . .
O1 O 0.6951(3) 0.3345(3) 0.14042(16) 0.0538(5) Uani 1 1 d . . . . .
O2 O 0.4647(4) 0.1587(2) 0.09491(17) 0.0555(6) Uani 1 1 d . . . . .
C1 C 0.2093(4) 0.5921(3) 0.10329(17) 0.0337(5) Uani 1 1 d . . . . .
N2 N -0.0065(3) 0.6864(2) 0.06569(15) 0.0366(4) Uani 1 1 d . . . . .
C12 C 0.1778(8) 0.2300(6) 0.5882(3) 0.0746(11) Uani 1 1 d . . . . .
C9 C 0.2471(5) 0.2521(4) 0.4771(2) 0.0529(7) Uani 1 1 d . . . . .
C8 C 0.4312(6) 0.3148(5) 0.4529(2) 0.0606(8) Uani 1 1 d . . . . .
H8 H 0.5114 0.3442 0.5060 0.073 Uiso 1 1 calc R U . . .
C7 C 0.4973(5) 0.3342(4) 0.3493(2) 0.0522(7) Uani 1 1 d . . . . .
H7 H 0.6211 0.3771 0.3326 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3779(4) 0.2891(3) 0.27139(19) 0.0381(5) Uani 1 1 d . . . . .
C5 C -0.0924(5) 0.8422(3) 0.0793(2) 0.0430(6) Uani 1 1 d . . . . .
H5 H -0.2411 0.9004 0.0517 0.052 Uiso 1 1 calc R U . . .
C4 C 0.0368(6) 0.9151(3) 0.1331(2) 0.0503(6) Uani 1 1 d . . . . .
H4 H -0.0233 1.0221 0.1446 0.060 Uiso 1 1 calc R U . . .
C10 C 0.1279(6) 0.2085(5) 0.3989(3) 0.0598(8) Uani 1 1 d . . . . .
H10 H 0.0048 0.1651 0.4157 0.072 Uiso 1 1 calc R U . . .
C11 C 0.1899(5) 0.2290(4) 0.2961(2) 0.0530(7) Uani 1 1 d . . . . .
H11 H 0.1057 0.2024 0.2433 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2626(6) 0.8245(3) 0.1704(2) 0.0522(7) Uani 1 1 d . . . . .
H3 H 0.3563 0.8727 0.2052 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3483(5) 0.6663(3) 0.1566(2) 0.0443(6) Uani 1 1 d . . . . .
H2 H 0.4985 0.6076 0.1825 0.053 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 1.440(2) . ?
S1 O2 1.443(2) . ?
S1 N1 1.5841(19) . ?
S1 C6 1.778(3) . ?
F1 C12 1.263(6) . ?
N1 C1 1.356(3) . ?
F3 C12 1.241(5) . ?
F2 C12 1.243(6) . ?
C1 N2 1.363(3) . ?
C1 C2 1.406(3) . ?
N2 C5 1.346(3) . ?
C12 C9 1.488(4) . ?
C9 C8 1.374(4) . ?
C9 C10 1.375(4) . ?
C8 C7 1.389(4) . ?
C7 C6 1.380(4) . ?
C6 C11 1.383(4) . ?
C5 C4 1.361(4) . ?
C4 C3 1.397(4) . ?
C10 C11 1.373(5) . ?
C3 C2 1.366(4) . ?

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 117.12(13) . . ?
O1 S1 N1 115.17(12) . . ?
O2 S1 N1 105.58(11) . . ?
O1 S1 C6 105.83(12) . . ?
O2 S1 C6 106.07(13) . . ?
N1 S1 C6 106.22(11) . . ?
C1 N1 S1 121.75(17) . . ?
N1 C1 N2 113.6(2) . . ?
N1 C1 C2 129.8(2) . . ?
N2 C1 C2 116.6(2) . . ?
C5 N2 C1 123.7(2) . . ?
F3 C12 F2 106.6(6) . . ?
F3 C12 F1 103.2(5) . . ?
F2 C12 F1 101.5(5) . . ?
F3 C12 C9 114.6(3) . . ?
F2 C12 C9 113.9(4) . . ?
F1 C12 C9 115.6(4) . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 C12 119.9(3) . . ?
C10 C9 C12 119.8(3) . . ?
C9 C8 C7 120.0(3) . . ?
C6 C7 C8 119.4(3) . . ?
C7 C6 C11 120.3(3) . . ?
C7 C6 S1 120.6(2) . . ?
C11 C6 S1 119.1(2) . . ?
N2 C5 C4 120.5(2) . . ?
C5 C4 C3 118.0(3) . . ?
C11 C10 C9 120.3(3) . . ?
C10 C11 C6 119.8(3) . . ?
C2 C3 C4 121.2(3) . . ?
C3 C2 C1 120.0(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
O1 S1 N1 C1 -48.4(2) . . . . ?
O2 S1 N1 C1 -179.2(2) . . . . ?
C6 S1 N1 C1 68.4(2) . . . . ?
S1 N1 C1 N2 -166.42(17) . . . . ?
S1 N1 C1 C2 14.2(4) . . . . ?
N1 C1 N2 C5 178.8(2) . . . . ?
C2 C1 N2 C5 -1.7(4) . . . . ?
F3 C12 C9 C8 146.6(6) . . . . ?
F2 C12 C9 C8 -90.2(6) . . . . ?
F1 C12 C9 C8 26.8(7) . . . . ?
F3 C12 C9 C10 -33.8(7) . . . . ?
F2 C12 C9 C10 89.3(6) . . . . ?
F1 C12 C9 C10 -153.7(5) . . . . ?
C10 C9 C8 C7 0.0(5) . . . . ?
C12 C9 C8 C7 179.5(3) . . . . ?
C9 C8 C7 C6 -0.4(5) . . . . ?
C8 C7 C6 C11 1.6(5) . . . . ?
C8 C7 C6 S1 -176.9(2) . . . . ?
O1 S1 C6 C7 11.3(3) . . . . ?
O2 S1 C6 C7 136.4(2) . . . . ?
N1 S1 C6 C7 -111.6(2) . . . . ?
O1 S1 C6 C11 -167.3(2) . . . . ?
O2 S1 C6 C11 -42.2(2) . . . . ?
N1 S1 C6 C11 69.9(2) . . . . ?
C1 N2 C5 C4 0.0(4) . . . . ?
N2 C5 C4 C3 2.0(4) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C12 C9 C10 C11 179.7(3) . . . . ?
C9 C10 C11 C6 2.0(5) . . . . ?
C7 C6 C11 C10 -2.4(5) . . . . ?
S1 C6 C11 C10 176.1(3) . . . . ?
C5 C4 C3 C2 -2.2(5) . . . . ?
C4 C3 C2 C1 0.5(5) . . . . ?
N1 C1 C2 C3 -179.2(3) . . . . ?
N2 C1 C2 C3 1.4(4) . . . . ?

_refine_diff_density_max         1.096
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.074

