# Electronic Supplementary Material (ESI) for Chemical Science.
# 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).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_mo_d8v218_0m
_database_code_depnum_ccdc_archive 'CCDC 1473889'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_audit_creation_date             2014-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2900 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H9 F12 N3 S'
_chemical_formula_sum            'C18 H9 F12 N3 S'
_chemical_formula_weight         527.34
_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'
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'

_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 21/c'
_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                   4.7617(3)
_cell_length_b                   31.515(3)
_cell_length_c                   13.2597(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.153(3)
_cell_angle_gamma                90
_cell_volume                     1988.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4204
_cell_measurement_temperature    122.15
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0772 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.8643.
The λ/2 correction factor is 0.0000.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.078
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11072
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.474
_diffrn_ambient_temperature      122.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2848
_reflns_number_total             3629
_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 (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (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    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.069
_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)+(0.0290P)²+4.6900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C13(H13), C14(H14), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
S1 S 1.52817(17) 0.56520(3) 0.44391(6) 0.0230(2) Uani 1 1 d . . . . .
F1 F 1.1072(5) 0.74926(7) 0.37687(18) 0.0469(6) Uani 1 1 d . . . . .
F2 F 0.4176(6) 0.30788(8) 0.3753(2) 0.0687(9) Uani 1 1 d . . . . .
F3 F 1.7073(5) 0.65431(9) 0.05276(18) 0.0530(7) Uani 1 1 d . . . . .
F4 F 1.5287(8) 0.71587(8) 0.0630(2) 0.0794(11) Uani 1 1 d . . . . .
F5 F 1.3079(5) 0.66628(9) -0.01480(17) 0.0543(7) Uani 1 1 d . . . . .
F6 F 0.3691(4) 0.45246(7) -0.01231(15) 0.0376(5) Uani 1 1 d . . . . .
F7 F -0.0298(4) 0.42796(8) 0.02886(16) 0.0401(6) Uani 1 1 d . . . . .
F8 F 0.1206(5) 0.48693(7) 0.09118(15) 0.0391(5) Uani 1 1 d . . . . .
F9 F 0.0470(4) 0.31308(7) 0.2812(2) 0.0456(6) Uani 1 1 d . . . . .
F10 F 0.4285(5) 0.29214(7) 0.2213(2) 0.0580(8) Uani 1 1 d . . . . .
F11 F 1.1105(5) 0.69999(8) 0.48648(16) 0.0492(6) Uani 1 1 d . . . . .
F12 F 0.7421(5) 0.71142(8) 0.39480(19) 0.0492(6) Uani 1 1 d . . . . .
N1 N 1.1527(6) 0.56242(9) 0.2898(2) 0.0247(6) Uani 1 1 d . . . . .
N2 N 1.1888(5) 0.50316(9) 0.3878(2) 0.0192(6) Uani 1 1 d . . . . .
H2 H 1.271(7) 0.4886(11) 0.432(3) 0.023 Uiso 1 1 d R . . . .
N3 N 0.9755(5) 0.48568(8) 0.32861(19) 0.0193(6) Uani 1 1 d . . . . .
C1 C 1.0205(7) 0.71008(11) 0.3932(3) 0.0278(8) Uani 1 1 d . . . . .
C2 C 1.1211(7) 0.67898(11) 0.3174(2) 0.0229(7) Uani 1 1 d . . . . .
C3 C 1.0870(7) 0.63629(11) 0.3362(2) 0.0228(7) Uani 1 1 d . . . . .
H3 H 0.9971 0.6273 0.3953 0.027 Uiso 1 1 calc R . . . .
C4 C 1.1836(7) 0.60655(10) 0.2692(2) 0.0213(7) Uani 1 1 d . . . . .
C5 C 1.2766(6) 0.54307(10) 0.3698(2) 0.0180(7) Uani 1 1 d . . . . .
C6 C 0.9019(6) 0.44805(10) 0.3509(2) 0.0197(7) Uani 1 1 d . . . . .
H6 H 0.9917 0.4338 0.4065 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6798(6) 0.42672(10) 0.2913(2) 0.0180(7) Uani 1 1 d . . . . .
C8 C 0.6029(6) 0.38559(10) 0.3160(2) 0.0197(7) Uani 1 1 d . . . . .
H8 H 0.6922 0.3719 0.3724 0.024 Uiso 1 1 calc R . . . .
C9 C 0.3973(6) 0.36439(10) 0.2591(2) 0.0201(7) Uani 1 1 d . . . . .
C10 C 0.3199(7) 0.31978(11) 0.2843(3) 0.0276(8) Uani 1 1 d . . . . .
C11 C 1.4688(8) 0.67531(12) 0.0666(3) 0.0330(8) Uani 1 1 d . . . . .
C12 C 1.3363(7) 0.66234(11) 0.1625(3) 0.0250(7) Uani 1 1 d . . . . .
C13 C 1.3062(7) 0.61935(11) 0.1819(2) 0.0240(7) Uani 1 1 d . . . . .
H13 H 1.3697 0.5989 0.1353 0.029 Uiso 1 1 calc R . . . .
C14 C 0.5458(6) 0.44654(10) 0.2083(2) 0.0205(7) Uani 1 1 d . . . . .
H14 H 0.5959 0.4746 0.1902 0.025 Uiso 1 1 calc R . . . .
C15 C 0.3389(6) 0.42491(11) 0.1526(2) 0.0207(7) Uani 1 1 d . . . . .
C16 C 0.1994(7) 0.44782(11) 0.0651(2) 0.0251(7) Uani 1 1 d . . . . .
C17 C 0.2643(7) 0.38387(11) 0.1769(2) 0.0225(7) Uani 1 1 d . . . . .
H17 H 0.1239 0.3693 0.1377 0.027 Uiso 1 1 calc R . . . .
C18 C 1.2449(7) 0.69251(11) 0.2292(2) 0.0245(7) Uani 1 1 d . . . . .
H18 H 1.2659 0.7219 0.2154 0.029 Uiso 1 1 calc R . . . .
H1 H 1.016(8) 0.5488(13) 0.259(3) 0.035(11) Uiso 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
S1 C5 1.673(3) . ?
F1 C1 1.323(4) . ?
F2 C10 1.331(4) . ?
F3 C11 1.333(4) . ?
F4 C11 1.311(4) . ?
F5 C11 1.331(4) . ?
F6 C16 1.338(4) . ?
F7 C16 1.332(4) . ?
F8 C16 1.338(4) . ?
F9 C10 1.315(4) . ?
F10 C10 1.326(4) . ?
F11 C1 1.332(4) . ?
F12 C1 1.327(4) . ?
N1 C4 1.426(4) . ?
N1 C5 1.341(4) . ?
N1 H1 0.87(4) . ?
N2 H2 0.83(4) . ?
N2 N3 1.375(4) . ?
N2 C5 1.349(4) . ?
N3 C6 1.275(4) . ?
C1 C2 1.496(5) . ?
C2 C3 1.379(5) . ?
C2 C18 1.396(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(5) . ?
C4 C13 1.376(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.460(4) . ?
C7 C8 1.389(4) . ?
C7 C14 1.398(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(4) . ?
C9 C10 1.494(5) . ?
C9 C17 1.384(5) . ?
C11 C12 1.497(5) . ?
C12 C13 1.388(5) . ?
C12 C18 1.380(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.388(4) . ?
C15 C16 1.500(5) . ?
C15 C17 1.383(5) . ?
C17 H17 0.9500 . ?
C18 H18 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
C4 N1 H1 118(3) . . ?
C5 N1 C4 123.3(3) . . ?
C5 N1 H1 116(3) . . ?
N3 N2 H2 120(2) . . ?
C5 N2 H2 120(3) . . ?
C5 N2 N3 120.0(3) . . ?
C6 N3 N2 116.4(3) . . ?
F1 C1 F11 106.5(3) . . ?
F1 C1 F12 106.9(3) . . ?
F1 C1 C2 113.1(3) . . ?
F11 C1 C2 111.6(3) . . ?
F12 C1 F11 106.2(3) . . ?
F12 C1 C2 112.1(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 C18 120.4(3) . . ?
C18 C2 C1 121.3(3) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 N1 119.9(3) . . ?
C13 C4 N1 119.8(3) . . ?
C13 C4 C3 120.3(3) . . ?
N1 C5 S1 124.0(2) . . ?
N1 C5 N2 115.7(3) . . ?
N2 C5 S1 120.3(2) . . ?
N3 C6 H6 119.9 . . ?
N3 C6 C7 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 C14 119.0(3) . . ?
C14 C7 C6 121.3(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 120.5(3) . . ?
C17 C9 C8 120.5(3) . . ?
C17 C9 C10 118.9(3) . . ?
F2 C10 C9 112.8(3) . . ?
F9 C10 F2 107.2(3) . . ?
F9 C10 F10 106.4(3) . . ?
F9 C10 C9 113.3(3) . . ?
F10 C10 F2 104.8(3) . . ?
F10 C10 C9 111.8(3) . . ?
F3 C11 C12 111.7(3) . . ?
F4 C11 F3 106.9(3) . . ?
F4 C11 F5 107.4(3) . . ?
F4 C11 C12 113.4(3) . . ?
F5 C11 F3 104.4(3) . . ?
F5 C11 C12 112.5(3) . . ?
C13 C12 C11 118.3(3) . . ?
C18 C12 C11 120.6(3) . . ?
C18 C12 C13 121.1(3) . . ?
C4 C13 C12 119.5(3) . . ?
C4 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C7 C14 H14 120.2 . . ?
C15 C14 C7 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 117.4(3) . . ?
C17 C15 C14 121.3(3) . . ?
C17 C15 C16 121.3(3) . . ?
F6 C16 C15 112.5(3) . . ?
F7 C16 F6 106.6(3) . . ?
F7 C16 F8 107.0(3) . . ?
F7 C16 C15 112.7(3) . . ?
F8 C16 F6 106.3(3) . . ?
F8 C16 C15 111.3(3) . . ?
C9 C17 H17 120.5 . . ?
C15 C17 C9 119.0(3) . . ?
C15 C17 H17 120.5 . . ?
C2 C18 H18 120.7 . . ?
C12 C18 C2 118.7(3) . . ?
C12 C18 H18 120.7 . . ?

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
F1 C1 C2 C3 168.7(3) . . . . ?
F1 C1 C2 C18 -11.7(5) . . . . ?
F3 C11 C12 C13 -48.7(5) . . . . ?
F3 C11 C12 C18 131.8(3) . . . . ?
F4 C11 C12 C13 -169.6(4) . . . . ?
F4 C11 C12 C18 10.9(5) . . . . ?
F5 C11 C12 C13 68.4(4) . . . . ?
F5 C11 C12 C18 -111.1(4) . . . . ?
F11 C1 C2 C3 48.7(4) . . . . ?
F11 C1 C2 C18 -131.7(3) . . . . ?
F12 C1 C2 C3 -70.3(4) . . . . ?
F12 C1 C2 C18 109.3(4) . . . . ?
N1 C4 C13 C12 -179.8(3) . . . . ?
N2 N3 C6 C7 -179.1(3) . . . . ?
N3 N2 C5 S1 177.9(2) . . . . ?
N3 N2 C5 N1 -3.0(4) . . . . ?
N3 C6 C7 C8 179.5(3) . . . . ?
N3 C6 C7 C14 0.8(5) . . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C1 C2 C18 C12 179.4(3) . . . . ?
C2 C3 C4 N1 178.9(3) . . . . ?
C2 C3 C4 C13 -2.0(5) . . . . ?
C3 C2 C18 C12 -1.1(5) . . . . ?
C3 C4 C13 C12 1.0(5) . . . . ?
C4 N1 C5 S1 -11.8(5) . . . . ?
C4 N1 C5 N2 169.2(3) . . . . ?
C5 N1 C4 C3 -63.1(4) . . . . ?
C5 N1 C4 C13 117.7(4) . . . . ?
C5 N2 N3 C6 -179.2(3) . . . . ?
C6 C7 C8 C9 -178.5(3) . . . . ?
C6 C7 C14 C15 178.9(3) . . . . ?
C7 C8 C9 C10 178.5(3) . . . . ?
C7 C8 C9 C17 -0.2(5) . . . . ?
C7 C14 C15 C16 179.3(3) . . . . ?
C7 C14 C15 C17 -0.6(5) . . . . ?
C8 C7 C14 C15 0.2(4) . . . . ?
C8 C9 C10 F2 14.3(5) . . . . ?
C8 C9 C10 F9 136.2(3) . . . . ?
C8 C9 C10 F10 -103.5(4) . . . . ?
C8 C9 C17 C15 -0.3(5) . . . . ?
C10 C9 C17 C15 -179.0(3) . . . . ?
C11 C12 C13 C4 -179.6(3) . . . . ?
C11 C12 C18 C2 179.6(3) . . . . ?
C13 C12 C18 C2 0.1(5) . . . . ?
C14 C7 C8 C9 0.2(4) . . . . ?
C14 C15 C16 F6 71.6(4) . . . . ?
C14 C15 C16 F7 -167.8(3) . . . . ?
C14 C15 C16 F8 -47.6(4) . . . . ?
C14 C15 C17 C9 0.7(5) . . . . ?
C16 C15 C17 C9 -179.2(3) . . . . ?
C17 C9 C10 F2 -167.0(3) . . . . ?
C17 C9 C10 F9 -45.1(4) . . . . ?
C17 C9 C10 F10 75.2(4) . . . . ?
C17 C15 C16 F6 -108.4(3) . . . . ?
C17 C15 C16 F7 12.1(4) . . . . ?
C17 C15 C16 F8 132.3(3) . . . . ?
C18 C2 C3 C4 2.0(5) . . . . ?
C18 C12 C13 C4 -0.1(5) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
####################################################################### 
# 
# 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_mo_d8v1111_0m
_database_code_depnum_ccdc_archive 'CCDC 1473890'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_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         'C16 H10 F6 N4 O2 S'
_chemical_formula_sum            'C16 H10 F6 N4 O2 S'
_chemical_formula_weight         436.34
_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'
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'

_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                   12.2715(14)
_cell_length_b                   8.4441(10)
_cell_length_c                   16.4877(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.794(4)
_cell_angle_gamma                90
_cell_volume                     1704.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7131
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1220 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.8319.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.115
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22730
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.147
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_min         2.476
_diffrn_ambient_temperature      122
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2404
_reflns_number_total             3029
_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       'Bruker Instrument Service'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  ?
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.302
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.031
_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)+(0.0764P)²+3.9500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1555
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C3(H3), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.67121(6) 0.46408(11) 0.99962(6) 0.0251(3) Uani 1 1 d . . . . .
F1 F 0.9336(2) 0.5694(6) 1.21834(19) 0.1096(17) Uani 1 1 d . . . . .
F2 F 1.0712(5) 0.7069(5) 1.2202(2) 0.140(2) Uani 1 1 d . . . . .
F3 F 1.0770(3) 0.4840(5) 1.17880(17) 0.1002(15) Uani 1 1 d . . . . .
F4 F 1.08950(15) 0.9747(2) 0.87493(12) 0.0264(5) Uani 1 1 d . . . . .
F5 F 1.21166(14) 0.9095(3) 0.96902(12) 0.0296(5) Uani 1 1 d . . . . .
F6 F 1.16375(15) 0.7449(2) 0.87425(12) 0.0272(5) Uani 1 1 d . . . . .
O1 O 0.3716(2) 1.6024(3) 0.77383(16) 0.0333(6) Uani 1 1 d . . . . .
O2 O 0.25842(19) 1.4880(3) 0.68622(15) 0.0290(6) Uani 1 1 d . . . . .
N1 N 0.7381(2) 0.7556(3) 0.95991(17) 0.0215(6) Uani 1 1 d . . . . .
H1 H 0.7210 0.8454 0.9351 0.026 Uiso 1 1 calc R . . . .
N2 N 0.5565(2) 0.7032(3) 0.93861(17) 0.0212(6) Uani 1 1 d . . . . .
H2 H 0.5001 0.6389 0.9388 0.025 Uiso 1 1 calc R . . . .
N3 N 0.5416(2) 0.8542(3) 0.91097(16) 0.0207(6) Uani 1 1 d . . . . .
N4 N 0.3277(2) 1.4839(3) 0.74404(17) 0.0233(7) Uani 1 1 d . . . . .
C1 C 1.0669(2) 0.7261(4) 1.0484(2) 0.0204(7) Uani 1 1 d . . . . .
H1A H 1.1413 0.7206 1.0682 0.025 Uiso 1 1 calc R . . . .
C2 C 0.9847(3) 0.6672(4) 1.0938(2) 0.0201(7) Uani 1 1 d . . . . .
C3 C 0.8759(2) 0.6720(4) 1.0651(2) 0.0205(7) Uani 1 1 d . . . . .
H3 H 0.8207 0.6307 1.0969 0.025 Uiso 1 1 calc R . . . .
C4 C 0.8486(2) 0.7377(4) 0.9894(2) 0.0190(7) Uani 1 1 d . . . . .
C5 C 0.6562(2) 0.6501(4) 0.9658(2) 0.0201(7) Uani 1 1 d . . . . .
C6 C 0.4447(2) 0.8872(4) 0.8811(2) 0.0214(7) Uani 1 1 d . . . . .
H6 H 0.3896 0.8082 0.8812 0.026 Uiso 1 1 calc R . . . .
C7 C 0.4176(2) 1.0419(4) 0.84733(19) 0.0205(7) Uani 1 1 d . . . . .
C8 C 0.3245(3) 1.0560(4) 0.7939(2) 0.0221(7) Uani 1 1 d . . . . .
H8 H 0.2806 0.9654 0.7817 0.027 Uiso 1 1 calc R . . . .
C9 C 0.2957(3) 1.1997(4) 0.7588(2) 0.0233(7) Uani 1 1 d . . . . .
H9 H 0.2333 1.2087 0.7218 0.028 Uiso 1 1 calc R . . . .
C10 C 0.3595(2) 1.3292(4) 0.7786(2) 0.0209(7) Uani 1 1 d . . . . .
C11 C 1.0154(3) 0.6066(4) 1.1773(2) 0.0227(7) Uani 1 1 d . . . . .
C12 C 1.0375(2) 0.7931(4) 0.9735(2) 0.0192(7) Uani 1 1 d . . . . .
C13 C 1.1252(2) 0.8551(4) 0.9229(2) 0.0213(7) Uani 1 1 d . . . . .
C14 C 0.9291(2) 0.7998(4) 0.9435(2) 0.0194(7) Uani 1 1 d . . . . .
H14 H 0.9103 0.8465 0.8920 0.023 Uiso 1 1 calc R . . . .
C15 C 0.4520(3) 1.3205(4) 0.8319(2) 0.0234(8) Uani 1 1 d . . . . .
H15 H 0.4943 1.4124 0.8448 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4810(3) 1.1771(4) 0.8656(2) 0.0223(7) Uani 1 1 d . . . . .
H16 H 0.5445 1.1692 0.9016 0.027 Uiso 1 1 calc R . . . .


_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 C5 1.673(4) . ?
F1 C11 1.287(4) . ?
F2 C11 1.274(5) . ?
F3 C11 1.281(4) . ?
F4 C13 1.338(4) . ?
F5 C13 1.345(4) . ?
F6 C13 1.336(4) . ?
O1 N4 1.224(4) . ?
O2 N4 1.235(4) . ?
N1 H1 0.8800 . ?
N1 C4 1.418(4) . ?
N1 C5 1.351(4) . ?
N2 H2 0.8800 . ?
N2 N3 1.363(4) . ?
N2 C5 1.351(4) . ?
N3 C6 1.287(4) . ?
N4 C10 1.467(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.388(5) . ?
C1 C12 1.385(5) . ?
C2 C3 1.388(4) . ?
C2 C11 1.493(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(5) . ?
C4 C14 1.387(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.450(5) . ?
C7 C8 1.400(5) . ?
C7 C16 1.404(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.372(5) . ?
C10 C15 1.390(5) . ?
C12 C13 1.498(4) . ?
C12 C14 1.389(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.369(5) . ?
C16 H16 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
C4 N1 H1 116.4 . . ?
C5 N1 H1 116.4 . . ?
C5 N1 C4 127.1(3) . . ?
N3 N2 H2 119.3 . . ?
C5 N2 H2 119.3 . . ?
C5 N2 N3 121.3(3) . . ?
C6 N3 N2 115.5(3) . . ?
O1 N4 O2 123.3(3) . . ?
O1 N4 C10 118.2(3) . . ?
O2 N4 C10 118.5(3) . . ?
C2 C1 H1A 120.9 . . ?
C12 C1 H1A 120.9 . . ?
C12 C1 C2 118.2(3) . . ?
C1 C2 C3 121.5(3) . . ?
C1 C2 C11 118.2(3) . . ?
C3 C2 C11 120.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 N1 121.3(3) . . ?
C3 C4 C14 120.3(3) . . ?
C14 C4 N1 118.1(3) . . ?
N1 C5 S1 125.2(2) . . ?
N2 C5 S1 119.9(2) . . ?
N2 C5 N1 114.8(3) . . ?
N3 C6 H6 119.2 . . ?
N3 C6 C7 121.7(3) . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 C16 118.9(3) . . ?
C16 C7 C6 122.7(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 N4 118.9(3) . . ?
C9 C10 C15 122.5(3) . . ?
C15 C10 N4 118.6(3) . . ?
F1 C11 C2 114.2(3) . . ?
F2 C11 F1 106.2(4) . . ?
F2 C11 F3 103.4(4) . . ?
F2 C11 C2 112.2(3) . . ?
F3 C11 F1 105.8(4) . . ?
F3 C11 C2 114.1(3) . . ?
C1 C12 C13 119.0(3) . . ?
C1 C12 C14 121.3(3) . . ?
C14 C12 C13 119.6(3) . . ?
F4 C13 F5 107.0(3) . . ?
F4 C13 C12 112.0(3) . . ?
F5 C13 C12 111.9(3) . . ?
F6 C13 F4 106.6(3) . . ?
F6 C13 F5 106.2(2) . . ?
F6 C13 C12 112.8(3) . . ?
C4 C14 C12 119.4(3) . . ?
C4 C14 H14 120.3 . . ?
C12 C14 H14 120.3 . . ?
C10 C15 H15 120.6 . . ?
C16 C15 C10 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C7 C16 H16 119.8 . . ?
C15 C16 C7 120.4(3) . . ?
C15 C16 H16 119.8 . . ?

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 N4 C10 C9 165.9(3) . . . . ?
O1 N4 C10 C15 -12.6(4) . . . . ?
O2 N4 C10 C9 -14.4(4) . . . . ?
O2 N4 C10 C15 167.1(3) . . . . ?
N1 C4 C14 C12 175.8(3) . . . . ?
N2 N3 C6 C7 -178.3(3) . . . . ?
N3 N2 C5 S1 179.7(2) . . . . ?
N3 N2 C5 N1 -2.6(4) . . . . ?
N3 C6 C7 C8 160.1(3) . . . . ?
N3 C6 C7 C16 -19.5(5) . . . . ?
N4 C10 C15 C16 178.8(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C2 C11 F1 173.2(4) . . . . ?
C1 C2 C11 F2 52.3(5) . . . . ?
C1 C2 C11 F3 -64.9(5) . . . . ?
C1 C12 C13 F4 -151.1(3) . . . . ?
C1 C12 C13 F5 -31.0(4) . . . . ?
C1 C12 C13 F6 88.7(4) . . . . ?
C1 C12 C14 C4 -0.2(5) . . . . ?
C2 C1 C12 C13 -179.1(3) . . . . ?
C2 C1 C12 C14 -0.9(5) . . . . ?
C2 C3 C4 N1 -175.4(3) . . . . ?
C2 C3 C4 C14 -0.9(5) . . . . ?
C3 C2 C11 F1 -3.3(5) . . . . ?
C3 C2 C11 F2 -124.2(5) . . . . ?
C3 C2 C11 F3 118.6(4) . . . . ?
C3 C4 C14 C12 1.1(5) . . . . ?
C4 N1 C5 S1 -8.0(5) . . . . ?
C4 N1 C5 N2 174.5(3) . . . . ?
C5 N1 C4 C3 -42.0(5) . . . . ?
C5 N1 C4 C14 143.3(3) . . . . ?
C5 N2 N3 C6 175.0(3) . . . . ?
C6 C7 C8 C9 -178.9(3) . . . . ?
C6 C7 C16 C15 179.8(3) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C8 C7 C16 C15 0.3(5) . . . . ?
C8 C9 C10 N4 -177.9(3) . . . . ?
C8 C9 C10 C15 0.6(5) . . . . ?
C9 C10 C15 C16 0.4(5) . . . . ?
C10 C15 C16 C7 -0.8(5) . . . . ?
C11 C2 C3 C4 176.1(3) . . . . ?
C12 C1 C2 C3 1.1(5) . . . . ?
C12 C1 C2 C11 -175.3(3) . . . . ?
C13 C12 C14 C4 178.0(3) . . . . ?
C14 C12 C13 F4 30.7(4) . . . . ?
C14 C12 C13 F5 150.8(3) . . . . ?
C14 C12 C13 F6 -89.5(4) . . . . ?
C16 C7 C8 C9 0.7(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT213_mo_d8v1111_0m       
;
PROBLEM: Atom F2              has ADP max/min Ratio .....        4.1 prolat
RESPONSE: The molecule contains a disordered triflouromethyl group
;
_vrf_PLAT242_mo_d8v1111_0m       
;
PROBLEM: Low       Ueq as Compared to Neighbors for .....        C11 Check 
RESPONSE: The molecule contains a disordered triflouromethyl group
;
# end Validation Reply Form

####################################################################### 
# 
# 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_mo_d8v1126_0m-a
_database_code_depnum_ccdc_archive 'CCDC 1473916'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_audit_creation_date             2016-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 F6 N5 O4 S'
_chemical_formula_sum            'C16 H9 F6 N5 O4 S'
_chemical_formula_weight         481.34
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8724(4)
_cell_length_b                   9.8446(5)
_cell_length_c                   12.3483(6)
_cell_angle_alpha                89.810(2)
_cell_angle_beta                 71.081(2)
_cell_angle_gamma                68.037(2)
_cell_volume                     937.66(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8691
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.17
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1296 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.9442.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.212
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21041
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.251
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3090
_reflns_number_total             3830
_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       ?
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(F6)=Sof(F4A)=Sof(F5A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6A)=FVAR(1)
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C13(H13), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.2316(2) 0.12015(18) 1.12099(13) 0.0359(4) Uani 1 1 d . . . . .
C2 C 0.0833(2) 0.1215(2) 1.10452(15) 0.0430(4) Uani 1 1 d . . . . .
H2 H 0.0171 0.2031 1.0782 0.052 Uiso 1 1 calc R . . . .
C3 C 0.0315(3) 0.0051(2) 1.12614(16) 0.0459(4) Uani 1 1 d . . . . .
H3 H -0.0688 0.0083 1.1156 0.055 Uiso 1 1 calc R . . . .
C4 C 0.1321(3) -0.1160(2) 1.16376(15) 0.0422(4) Uani 1 1 d . . . . .
C5 C 0.2779(2) -0.12298(19) 1.18392(14) 0.0394(4) Uani 1 1 d . . . . .
H5 H 0.3425 -0.2047 1.2110 0.047 Uiso 1 1 calc R . . . .
C6 C 0.3255(2) -0.00397(18) 1.16251(13) 0.0351(4) Uani 1 1 d . . . . .
C7 C 0.2802(2) 0.24768(19) 1.09664(14) 0.0385(4) Uani 1 1 d . . . . .
H7 H 0.3255 0.2815 1.1438 0.046 Uiso 1 1 calc R . . . .
C10 C 0.3087(2) 0.49560(19) 0.89538(15) 0.0384(4) Uani 1 1 d . . . . .
C12 C 0.2500(2) 0.47893(19) 0.71232(14) 0.0367(4) Uani 1 1 d . . . . .
C13 C 0.2595(2) 0.3684(2) 0.63797(15) 0.0405(4) Uani 1 1 d . . . . .
H13 H 0.2659 0.2776 0.6623 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2594(3) 0.3931(2) 0.52783(16) 0.0457(4) Uani 1 1 d . . . . .
C15 C 0.2494(3) 0.5274(2) 0.49003(16) 0.0492(5) Uani 1 1 d . . . . .
H15 H 0.2511 0.5431 0.4154 0.059 Uiso 1 1 calc R . . . .
C16 C 0.2369(2) 0.6374(2) 0.56510(16) 0.0442(4) Uani 1 1 d . . . . .
C17 C 0.2384(2) 0.6147(2) 0.67569(15) 0.0413(4) Uani 1 1 d . . . . .
H17 H 0.2318 0.6898 0.7248 0.050 Uiso 1 1 calc R . . . .
C19 C 0.2144(3) 0.7877(3) 0.5297(2) 0.0598(6) Uani 1 1 d . . . . .
C20 C 0.2733(4) 0.2721(3) 0.4480(2) 0.0684(7) Uani 1 1 d . . . . .
N8 N 0.2586(2) 0.31062(16) 1.00918(12) 0.0394(3) Uani 1 1 d . . . . .
N11 N 0.2481(2) 0.44591(17) 0.82468(13) 0.0433(4) Uani 1 1 d . . . . .
N20 N 0.4875(2) -0.01833(16) 1.17865(12) 0.0401(3) Uani 1 1 d . . . . .
N21 N 0.0834(3) -0.2441(2) 1.18130(14) 0.0536(4) Uani 1 1 d . . . . .
N22 N 0.3061(2) 0.42809(17) 0.99196(13) 0.0437(4) Uani 1 1 d . . . . .
O22 O -0.0344(2) -0.2428(2) 1.14969(16) 0.0751(5) Uani 1 1 d . . . . .
O23 O 0.1647(3) -0.34539(18) 1.22284(15) 0.0741(5) Uani 1 1 d . . . . .
O24 O 0.5358(2) -0.10308(17) 1.24402(13) 0.0605(4) Uani 1 1 d . . . . .
O25 O 0.56723(19) 0.05227(16) 1.12422(13) 0.0541(4) Uani 1 1 d . . . . .
F1 F 0.2009(18) 0.3101(12) 0.3722(8) 0.117(4) Uani 0.480(19) 1 d . . P A 1
F2 F 0.4143(16) 0.179(2) 0.401(2) 0.189(8) Uani 0.480(19) 1 d . . P A 1
F3 F 0.170(3) 0.2047(19) 0.5099(8) 0.131(4) Uani 0.480(19) 1 d . . P A 1
F4 F 0.0951(11) 0.8326(9) 0.4805(12) 0.126(4) Uani 0.423(9) 1 d . . P B 1
F5 F 0.178(2) 0.8886(6) 0.6069(4) 0.138(6) Uani 0.423(9) 1 d . . P B 1
F6 F 0.2345(15) 0.7995(5) 0.4259(3) 0.136(4) Uani 0.577(9) 1 d . . P B 2
S1 S 0.38306(8) 0.62992(6) 0.87867(5) 0.05768(18) Uani 1 1 d . . . . .
F4A F 0.0545(5) 0.8852(4) 0.5890(5) 0.0891(16) Uani 0.577(9) 1 d . . P B 2
F5A F 0.3134(10) 0.8403(7) 0.5595(9) 0.126(3) Uani 0.577(9) 1 d . . P B 2
F6A F 0.3497(8) 0.7812(7) 0.4426(8) 0.113(3) Uani 0.423(9) 1 d . . P B 1
H11 H 0.220(3) 0.375(3) 0.8476(19) 0.053(6) Uiso 1 1 d . . . . .
H22 H 0.357(3) 0.451(3) 1.033(2) 0.061(7) Uiso 1 1 d . . . . .
F3A F 0.285(2) 0.1493(8) 0.4887(6) 0.103(3) Uani 0.520(19) 1 d . . P A 2
F1A F 0.1534(13) 0.3213(13) 0.4006(11) 0.127(3) Uani 0.520(19) 1 d . . P A 2
F2A F 0.4232(13) 0.2312(10) 0.3551(5) 0.104(3) Uani 0.520(19) 1 d . . P A 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
C1 C2 1.390(3) . ?
C1 C6 1.401(2) . ?
C1 C7 1.473(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.373(3) . ?
C4 N21 1.473(2) . ?
C5 C6 1.384(2) . ?
C6 N20 1.469(2) . ?
C7 N8 1.276(2) . ?
C10 N11 1.340(2) . ?
C10 N22 1.361(2) . ?
C10 S1 1.6702(18) . ?
C12 C13 1.386(3) . ?
C12 C17 1.388(2) . ?
C12 N11 1.420(2) . ?
C13 C14 1.381(2) . ?
C14 C15 1.382(3) . ?
C14 C20 1.492(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.387(2) . ?
C16 C19 1.500(3) . ?
C19 F4 1.323(6) . ?
C19 F5 1.251(6) . ?
C19 F6 1.247(4) . ?
C19 F4A 1.336(4) . ?
C19 F5A 1.314(5) . ?
C19 F6A 1.307(5) . ?
C20 F1 1.279(8) . ?
C20 F2 1.191(9) . ?
C20 F3 1.363(9) . ?
C20 F3A 1.289(6) . ?
C20 F1A 1.313(7) . ?
C20 F2A 1.364(7) . ?
N8 N22 1.366(2) . ?
N20 O24 1.2182(19) . ?
N20 O25 1.221(2) . ?
N21 O22 1.224(2) . ?
N21 O23 1.215(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
C2 C1 C6 117.03(16) . . ?
C2 C1 C7 119.40(15) . . ?
C6 C1 C7 123.56(16) . . ?
C3 C2 C1 121.83(17) . . ?
C4 C3 C2 118.51(18) . . ?
C3 C4 N21 119.05(18) . . ?
C5 C4 C3 122.49(17) . . ?
C5 C4 N21 118.46(17) . . ?
C4 C5 C6 117.63(16) . . ?
C1 C6 N20 121.12(15) . . ?
C5 C6 C1 122.47(17) . . ?
C5 C6 N20 116.30(15) . . ?
N8 C7 C1 118.34(16) . . ?
N11 C10 N22 114.90(16) . . ?
N11 C10 S1 127.52(13) . . ?
N22 C10 S1 117.58(14) . . ?
C13 C12 C17 119.52(15) . . ?
C13 C12 N11 116.74(15) . . ?
C17 C12 N11 123.71(16) . . ?
C14 C13 C12 120.11(17) . . ?
C13 C14 C15 120.90(18) . . ?
C13 C14 C20 119.50(19) . . ?
C15 C14 C20 119.59(19) . . ?
C16 C15 C14 118.62(17) . . ?
C15 C16 C17 121.47(17) . . ?
C15 C16 C19 120.08(17) . . ?
C17 C16 C19 118.41(19) . . ?
C16 C17 C12 119.37(18) . . ?
F4 C19 C16 110.6(3) . . ?
F5 C19 C16 116.9(3) . . ?
F5 C19 F4 107.8(6) . . ?
F5 C19 F6A 109.5(6) . . ?
F6 C19 C16 116.6(3) . . ?
F6 C19 F4A 105.6(4) . . ?
F6 C19 F5A 108.8(4) . . ?
F4A C19 C16 109.9(2) . . ?
F5A C19 C16 111.7(2) . . ?
F5A C19 F4A 103.1(4) . . ?
F6A C19 C16 110.9(3) . . ?
F6A C19 F4 99.7(5) . . ?
F1 C20 C14 117.2(6) . . ?
F1 C20 F3 97.4(6) . . ?
F2 C20 C14 116.9(5) . . ?
F2 C20 F1 107.8(9) . . ?
F2 C20 F3 107.7(8) . . ?
F3 C20 C14 107.8(5) . . ?
F3A C20 C14 116.0(3) . . ?
F3A C20 F1A 113.7(7) . . ?
F3A C20 F2A 102.8(6) . . ?
F1A C20 C14 110.3(5) . . ?
F1A C20 F2A 102.8(6) . . ?
F2A C20 C14 110.1(4) . . ?
C7 N8 N22 115.16(15) . . ?
C10 N11 C12 129.60(16) . . ?
O24 N20 C6 117.51(15) . . ?
O24 N20 O25 124.05(17) . . ?
O25 N20 C6 118.42(14) . . ?
O22 N21 C4 117.18(18) . . ?
O23 N21 C4 118.46(18) . . ?
O23 N21 O22 124.33(19) . . ?
C10 N22 N8 121.68(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_d8v1154_0m
_database_code_depnum_ccdc_archive 'CCDC 1473891'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_audit_creation_date             2015-06-05
_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         'C18 H13 F6 N3 O2 S'
_chemical_formula_sum            'C18 H13 F6 N3 O2 S'
_chemical_formula_weight         449.37
_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                   12.2731(16)
_cell_length_b                   9.2592(14)
_cell_length_c                   16.180(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.897(5)
_cell_angle_gamma                90
_cell_volume                     1837.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    100(30)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0773 after correction.
The Ratio of minimum to maximum transmission is 0.9015.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             912
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.325
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22131
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.479
_diffrn_reflns_theta_min         2.519
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          'temperature uncertainty +- 30K'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3274
_reflns_number_total             3785
_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       'Bruker Instrument Service'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  ?
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+1.3410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.67234(3) -0.03885(4) 0.48000(3) 0.02504(12) Uani 1 1 d . . . . .
F1 F 1.07794(9) 0.48110(12) 0.37817(7) 0.0327(3) Uani 1 1 d . . . . .
F2 F 1.19626(8) 0.41936(13) 0.47244(7) 0.0352(3) Uani 1 1 d . . . . .
F3 F 1.16524(9) 0.28112(12) 0.36813(7) 0.0348(3) Uani 1 1 d . . . . .
N4 N 0.53867(10) 0.32294(14) 0.40353(8) 0.0181(3) Uani 1 1 d . . . . .
O5 O 0.38924(11) 1.04029(13) 0.30282(9) 0.0319(3) Uani 1 1 d . . . . .
O0AA O 0.26530(10) 0.94813(12) 0.21298(8) 0.0254(3) Uani 1 1 d . . . . .
C7 C 1.05851(12) 0.21833(17) 0.54044(10) 0.0178(3) Uani 1 1 d . . . . .
H7 H 1.1326 0.2129 0.5591 0.021 Uiso 1 1 calc R . . . .
N8 N 0.55564(11) 0.17998(15) 0.42346(9) 0.0197(3) Uani 1 1 d . . . . .
C9 C 0.41868(12) 0.50266(17) 0.34675(10) 0.0175(3) Uani 1 1 d . . . . .
F10 F 0.95050(12) -0.03402(14) 0.68111(8) 0.0504(4) Uani 1 1 d . . . . .
F11 F 1.10983(9) 0.05600(18) 0.67749(8) 0.0581(4) Uani 1 1 d . . . . .
C12 C 0.65449(12) 0.13411(17) 0.45238(10) 0.0183(3) Uani 1 1 d . . . . .
N13 N 0.73225(11) 0.23865(16) 0.45413(9) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.84127(12) 0.22625(17) 0.48344(10) 0.0177(3) Uani 1 1 d . . . . .
C15 C 0.36715(13) 0.78425(17) 0.29666(10) 0.0181(3) Uani 1 1 d . . . . .
C16 C 0.92161(12) 0.29587(17) 0.43910(10) 0.0179(3) Uani 1 1 d . . . . .
H16 H 0.9029 0.3452 0.3891 0.021 Uiso 1 1 calc R . . . .
C17 C 0.33416(13) 0.52802(18) 0.28883(11) 0.0209(3) Uani 1 1 d . . . . .
H17 H 0.2939 0.4489 0.2662 0.025 Uiso 1 1 calc R . . . .
C18 C 0.34384(13) 0.93644(17) 0.27249(10) 0.0197(3) Uani 1 1 d . . . . .
C19 C 0.45087(13) 0.75954(18) 0.35547(11) 0.0221(4) Uani 1 1 d . . . . .
H19 H 0.4908 0.8387 0.3784 0.026 Uiso 1 1 calc R . . . .
C20 C 0.47604(13) 0.62036(18) 0.38058(10) 0.0215(3) Uani 1 1 d . . . . .
H20 H 0.5326 0.6046 0.4211 0.026 Uiso 1 1 calc R . . . .
F21 F 0.98093(13) 0.17599(15) 0.72847(7) 0.0557(4) Uani 1 1 d . . . . .
C22 C 1.11655(13) 0.36812(18) 0.42178(10) 0.0214(3) Uani 1 1 d . . . . .
C23 C 0.86855(13) 0.15632(17) 0.55724(10) 0.0187(3) Uani 1 1 d . . . . .
H23 H 0.8138 0.1119 0.5887 0.022 Uiso 1 1 calc R . . . .
C24 C 0.97724(12) 0.15230(17) 0.58437(10) 0.0178(3) Uani 1 1 d . . . . .
C25 C 0.44549(12) 0.35336(17) 0.36975(10) 0.0194(3) Uani 1 1 d . . . . .
H25 H 0.3936 0.2788 0.3596 0.023 Uiso 1 1 calc R . . . .
C26 C 0.30822(13) 0.66754(18) 0.26395(10) 0.0207(3) Uani 1 1 d . . . . .
H26 H 0.2503 0.6836 0.2246 0.025 Uiso 1 1 calc R . . . .
C27 C 1.02942(12) 0.29249(17) 0.46863(10) 0.0175(3) Uani 1 1 d . . . . .
C28 C 1.00496(13) 0.08641(19) 0.66726(11) 0.0229(4) Uani 1 1 d . . . . .
C6 C 0.23666(16) 1.09476(19) 0.18956(12) 0.0306(4) Uani 1 1 d . . . . .
H6A H 0.1744 1.0931 0.1501 0.046 Uiso 1 1 calc GR . . . .
H6B H 0.2990 1.1409 0.1640 0.046 Uiso 1 1 calc GR . . . .
H6C H 0.2172 1.1493 0.2389 0.046 Uiso 1 1 calc GR . . . .
H13 H 0.7134(17) 0.314(2) 0.4313(13) 0.032(6) Uiso 1 1 d . . . . .
H8 H 0.5034(18) 0.117(2) 0.4182(14) 0.037(6) Uiso 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
S1 C12 1.6751(17) . ?
F1 C22 1.340(2) . ?
F2 C22 1.3419(19) . ?
F3 C22 1.339(2) . ?
N4 N8 1.3766(19) . ?
N4 C25 1.282(2) . ?
O5 C18 1.207(2) . ?
O0AA C18 1.344(2) . ?
O0AA C6 1.450(2) . ?
C7 C24 1.386(2) . ?
C7 C27 1.386(2) . ?
N8 C12 1.354(2) . ?
C9 C17 1.395(2) . ?
C9 C20 1.399(2) . ?
C9 C25 1.466(2) . ?
F10 C28 1.323(2) . ?
F11 C28 1.323(2) . ?
C12 N13 1.359(2) . ?
N13 C14 1.409(2) . ?
C14 C16 1.396(2) . ?
C14 C23 1.390(2) . ?
C15 C18 1.488(2) . ?
C15 C19 1.396(2) . ?
C15 C26 1.395(2) . ?
C16 C27 1.392(2) . ?
C17 C26 1.387(2) . ?
C19 C20 1.383(2) . ?
F21 C28 1.332(2) . ?
C22 C27 1.504(2) . ?
C23 C24 1.391(2) . ?
C24 C28 1.502(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
C25 N4 N8 115.91(13) . . ?
C18 O0AA C6 115.13(13) . . ?
C24 C7 C27 118.59(14) . . ?
C12 N8 N4 120.62(13) . . ?
C17 C9 C20 119.02(15) . . ?
C17 C9 C25 119.02(14) . . ?
C20 C9 C25 121.96(14) . . ?
N8 C12 S1 119.99(12) . . ?
N8 C12 N13 113.85(14) . . ?
N13 C12 S1 126.15(12) . . ?
C12 N13 C14 127.39(14) . . ?
C16 C14 N13 117.92(14) . . ?
C23 C14 N13 121.75(14) . . ?
C23 C14 C16 120.17(14) . . ?
C19 C15 C18 117.73(14) . . ?
C26 C15 C18 122.77(14) . . ?
C26 C15 C19 119.50(15) . . ?
C27 C16 C14 119.51(15) . . ?
C26 C17 C9 120.69(15) . . ?
O5 C18 O0AA 122.51(15) . . ?
O5 C18 C15 124.43(15) . . ?
O0AA C18 C15 113.07(14) . . ?
C20 C19 C15 120.34(15) . . ?
C19 C20 C9 120.41(15) . . ?
F1 C22 F2 106.48(14) . . ?
F1 C22 C27 112.58(13) . . ?
F2 C22 C27 111.89(13) . . ?
F3 C22 F1 106.61(14) . . ?
F3 C22 F2 106.06(13) . . ?
F3 C22 C27 112.74(14) . . ?
C14 C23 C24 119.01(15) . . ?
C7 C24 C23 121.69(15) . . ?
C7 C24 C28 119.44(14) . . ?
C23 C24 C28 118.63(14) . . ?
N4 C25 C9 120.32(14) . . ?
C17 C26 C15 120.02(15) . . ?
C7 C27 C16 120.96(14) . . ?
C7 C27 C22 119.03(14) . . ?
C16 C27 C22 120.00(14) . . ?
F10 C28 F21 105.86(15) . . ?
F10 C28 C24 113.13(14) . . ?
F11 C28 F10 107.12(15) . . ?
F11 C28 F21 106.14(15) . . ?
F11 C28 C24 112.88(14) . . ?
F21 C28 C24 111.20(14) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
