# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 
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data_mo_15aw017_0ma
_database_code_depnum_ccdc_archive 'CCDC 1497477'
#Added by publCIF



_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;


_refine_ls_number_constraints    5
# publcif _publ_body_element loop end
_audit_creation_date             2015-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H7 F3 N2 O S'
_chemical_formula_sum            'C14 H7 F3 N2 O S'
_chemical_formula_weight         308.28
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9995(8)
_cell_length_b                   12.9029(8)
_cell_length_c                   10.0701(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.081(2)
_cell_angle_gamma                90
_cell_volume                     1333.55(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6458
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.418
_cell_measurement_theta_min      3.158
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0702 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.7992.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19925
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         3.158
_diffrn_ambient_temperature      100
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2158
_reflns_number_total             3059
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+2.4718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1324
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(C4A) = Uiso(S1A) = Uiso(C1A) = Uiso(C2A) = Uiso(C3A)
3. Rigid body (RIGU) restrains
 C4, C3, C2, C1, S1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: H5A(0.75) H5B(0.75) H5BC(0.25) H5BD(0.25) S1(0.75) C4(0.75)
 C1(0.75) H1(0.75) C2(0.75) H2(0.75) C3(0.75) H3(0.75) S1A(0.25) C1A(0.25)
 H1A(0.25) C4A(0.25) C3A(0.25) H3A(0.25) C2A(0.25) H2A(0.25)
5.a Free rotating group:
 S1(C4,C1,C2,C3), S1A(C1A,C4A,C3A,C2A)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C5(H5BC,H5BD), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C1A(H1A), C3A(H3A), C2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F3 F 0.42621(15) 0.51362(12) 0.58129(17) 0.0344(4) Uani 1 1 d . . . . .
F1 F 0.03355(14) 0.41433(13) 0.63418(16) 0.0349(4) Uani 1 1 d . . . . .
F2 F 0.03169(15) 0.59112(14) 0.77074(17) 0.0399(4) Uani 1 1 d . . . . .
O1 O 0.21665(19) 0.36618(13) 0.53728(19) 0.0310(4) Uani 1 1 d . . . . .
N2 N 0.4988(3) 0.7652(2) 0.7119(3) 0.0438(6) Uani 1 1 d . . . . .
C7 C 0.2288(3) 0.45781(19) 0.6021(2) 0.0254(5) Uani 1 1 d . . . . .
C11 C 0.3259(3) 0.62466(19) 0.6924(3) 0.0271(5) Uani 1 1 d . . . . .
C10 C 0.2255(3) 0.64673(19) 0.7432(2) 0.0274(5) Uani 1 1 d . . . . .
C9 C 0.1300(2) 0.5737(2) 0.7243(2) 0.0274(5) Uani 1 1 d . . . . .
C8 C 0.1309(2) 0.4818(2) 0.6548(2) 0.0265(5) Uani 1 1 d . . . . .
C12 C 0.3267(3) 0.53119(19) 0.6256(3) 0.0263(5) Uani 1 1 d . . . . .
N1 N 0.2201(3) 0.8233(2) 0.8610(3) 0.0519(7) Uani 1 1 d . . . . .
C5 C 0.2227(3) 0.2479(2) 0.3592(3) 0.0330(6) Uani 1 1 d . . . . .
H5A H 0.1284 0.2616 0.3110 0.040 Uiso 0.75 1 calc R . P A 1
H5B H 0.2599 0.2347 0.2847 0.040 Uiso 0.75 1 calc R . P A 1
H5BC H 0.1287 0.2620 0.3100 0.040 Uiso 0.25 1 calc R . P B 2
H5BD H 0.2607 0.2342 0.2855 0.040 Uiso 0.25 1 calc R . P B 2
C13 C 0.4241(3) 0.7007(2) 0.7039(3) 0.0323(6) Uani 1 1 d . . . . .
C6 C 0.2871(3) 0.3436(2) 0.4429(3) 0.0313(6) Uani 1 1 d . . . . .
H6A H 0.3801 0.3300 0.4986 0.038 Uiso 1 1 calc R . . . .
H6B H 0.2809 0.4026 0.3780 0.038 Uiso 1 1 calc R . . . .
C14 C 0.2220(3) 0.7441(2) 0.8100(3) 0.0364(7) Uani 1 1 d . . . . .
S1 S 0.37505(9) 0.07814(8) 0.49603(12) 0.0320(2) Uani 0.75 1 d . U P C 1
C4 C 0.2400(2) 0.1519(2) 0.4508(4) 0.0274(7) Uani 0.75 1 d G U P C 1
C1 C 0.3236(4) -0.0048(3) 0.5919(6) 0.0401(11) Uani 0.75 1 d G U P C 1
H1 H 0.3721 -0.0631 0.6406 0.048 Uiso 0.75 1 calc R . P C 1
C2 C 0.2023(4) 0.0218(4) 0.5916(7) 0.0414(10) Uani 0.75 1 d G U P C 1
H2 H 0.1567 -0.0159 0.6401 0.050 Uiso 0.75 1 calc R . P C 1
C3 C 0.15342(19) 0.1132(3) 0.5093(4) 0.0286(10) Uani 0.75 1 d G U P C 1
H3 H 0.0713 0.1436 0.4964 0.034 Uiso 0.75 1 calc R . P C 1
S1A S 0.1230(4) 0.1206(4) 0.5090(6) 0.0351(8) Uiso 0.25 1 d . . P C 2
C1A C 0.2057(12) 0.0151(11) 0.592(2) 0.0351(8) Uiso 0.25 1 d G . P C 2
H1A H 0.1756 -0.0323 0.6457 0.042 Uiso 0.25 1 calc R . P C 2
C4A C 0.2376(9) 0.1571(9) 0.4460(15) 0.0351(8) Uiso 0.25 1 d G . P C 2
C3A C 0.3416(7) 0.0896(9) 0.4868(14) 0.0351(8) Uiso 0.25 1 d G . P C 2
H3A H 0.4164 0.0972 0.4615 0.042 Uiso 0.25 1 calc R . P C 2
C2A C 0.3231(12) 0.0068(11) 0.572(2) 0.0351(8) Uiso 0.25 1 d G . P C 2
H2A H 0.3842 -0.0473 0.6103 0.042 Uiso 0.25 1 calc R . P C 2


_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
F3 C12 1.342(3) . ?
F1 C8 1.337(3) . ?
F2 C9 1.342(3) . ?
O1 C7 1.334(3) . ?
O1 C6 1.455(3) . ?
N2 C13 1.151(4) . ?
C7 C8 1.396(3) . ?
C7 C12 1.389(4) . ?
C11 C10 1.403(4) . ?
C11 C12 1.382(3) . ?
C11 C13 1.433(4) . ?
C10 C9 1.373(4) . ?
C10 C14 1.432(4) . ?
C9 C8 1.378(4) . ?
N1 C14 1.147(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5BC 0.9900 . ?
C5 H5BD 0.9900 . ?
C5 C6 1.518(4) . ?
C5 C4 1.515(3) . ?
C5 C4A 1.436(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
S1 C4 1.6832 . ?
S1 C1 1.6706 . ?
C4 C3 1.3809 . ?
C1 H1 0.9500 . ?
C1 C2 1.3771 . ?
C2 H2 0.9500 . ?
C2 C3 1.4309 . ?
C3 H3 0.9500 . ?
S1A C1A 1.6831 . ?
S1A C4A 1.6693 . ?
C1A H1A 0.9500 . ?
C1A C2A 1.3815 . ?
C4A C3A 1.3775 . ?
C3A H3A 0.9500 . ?
C3A C2A 1.4305 . ?
C2A H2A 0.9500 . ?

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
C7 O1 C6 120.9(2) . . ?
O1 C7 C8 115.3(2) . . ?
O1 C7 C12 128.5(2) . . ?
C12 C7 C8 116.2(2) . . ?
C10 C11 C13 120.1(2) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 C13 120.0(2) . . ?
C11 C10 C14 120.5(3) . . ?
C9 C10 C11 118.3(2) . . ?
C9 C10 C14 121.2(2) . . ?
F2 C9 C10 120.6(2) . . ?
F2 C9 C8 118.3(2) . . ?
C10 C9 C8 121.1(2) . . ?
F1 C8 C7 118.7(2) . . ?
F1 C8 C9 119.2(2) . . ?
C9 C8 C7 122.1(2) . . ?
F3 C12 C7 120.2(2) . . ?
F3 C12 C11 117.3(2) . . ?
C11 C12 C7 122.5(2) . . ?
H5A C5 H5B 107.7 . . ?
H5BC C5 H5BD 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C6 C5 H5BC 108.9 . . ?
C6 C5 H5BD 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.3(3) . . ?
C4A C5 H5BC 108.9 . . ?
C4A C5 H5BD 108.9 . . ?
C4A C5 C6 113.4(7) . . ?
N2 C13 C11 177.0(3) . . ?
O1 C6 C5 105.9(2) . . ?
O1 C6 H6A 110.6 . . ?
O1 C6 H6B 110.6 . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
N1 C14 C10 178.3(3) . . ?
C1 S1 C4 94.0 . . ?
C5 C4 S1 122.18(17) . . ?
C3 C4 C5 126.89(17) . . ?
C3 C4 S1 110.9 . . ?
S1 C1 H1 124.2 . . ?
C2 C1 S1 111.6 . . ?
C2 C1 H1 124.2 . . ?
C1 C2 H2 124.2 . . ?
C1 C2 C3 111.6 . . ?
C3 C2 H2 124.2 . . ?
C4 C3 C2 111.8 . . ?
C4 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
C4A S1A C1A 94.0 . . ?
S1A C1A H1A 124.6 . . ?
C2A C1A S1A 110.9 . . ?
C2A C1A H1A 124.6 . . ?
C5 C4A S1A 121.7(4) . . ?
C3A C4A C5 126.7(4) . . ?
C3A C4A S1A 111.6 . . ?
C4A C3A H3A 124.2 . . ?
C4A C3A C2A 111.6 . . ?
C2A C3A H3A 124.2 . . ?
C1A C2A C3A 111.9 . . ?
C1A C2A H2A 124.1 . . ?
C3A C2A H2A 124.1 . . ?

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 C9 C8 F1 1.0(3) . . . . ?
F2 C9 C8 C7 179.4(2) . . . . ?
O1 C7 C8 F1 -1.5(3) . . . . ?
O1 C7 C8 C9 -180.0(2) . . . . ?
O1 C7 C12 F3 -0.3(4) . . . . ?
O1 C7 C12 C11 178.7(2) . . . . ?
C7 O1 C6 C5 -164.8(2) . . . . ?
C11 C10 C9 F2 -179.9(2) . . . . ?
C11 C10 C9 C8 -1.3(3) . . . . ?
C10 C11 C12 F3 -178.9(2) . . . . ?
C10 C11 C12 C7 2.0(4) . . . . ?
C10 C9 C8 F1 -177.6(2) . . . . ?
C10 C9 C8 C7 0.8(4) . . . . ?
C8 C7 C12 F3 178.6(2) . . . . ?
C8 C7 C12 C11 -2.4(4) . . . . ?
C12 C7 C8 F1 179.5(2) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C12 C11 C10 C9 -0.1(3) . . . . ?
C12 C11 C10 C14 -178.7(2) . . . . ?
C5 C4 C3 C2 -179.2(5) . . . . ?
C5 C4A C3A C2A -179(2) . . . . ?
C13 C11 C10 C9 177.0(2) . . . . ?
C13 C11 C10 C14 -1.6(4) . . . . ?
C13 C11 C12 F3 3.9(3) . . . . ?
C13 C11 C12 C7 -175.1(2) . . . . ?
C6 O1 C7 C8 162.1(2) . . . . ?
C6 O1 C7 C12 -19.0(4) . . . . ?
C6 C5 C4 S1 -83.3(4) . . . . ?
C6 C5 C4 C3 95.8(4) . . . . ?
C6 C5 C4A S1A 95.4(11) . . . . ?
C6 C5 C4A C3A -85.2(12) . . . . ?
C14 C10 C9 F2 -1.2(4) . . . . ?
C14 C10 C9 C8 177.3(2) . . . . ?
S1 C4 C3 C2 0.0 . . . . ?
S1 C1 C2 C3 0.0 . . . . ?
C4 C5 C6 O1 -65.8(3) . . . . ?
C4 S1 C1 C2 0.0 . . . . ?
C1 S1 C4 C5 179.2(5) . . . . ?
C1 S1 C4 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
S1A C1A C2A C3A 0.0 . . . . ?
S1A C4A C3A C2A 0.0 . . . . ?
C1A S1A C4A C5 179.5(19) . . . . ?
C1A S1A C4A C3A 0.0 . . . . ?
C4A C5 C6 O1 -65.1(4) . . . . ?
C4A S1A C1A C2A 0.0 . . . . ?
C4A C3A C2A C1A 0.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
