# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_201803177
_database_code_depnum_ccdc_archive 'CCDC 1838811'
loop_
_audit_author_name
_audit_author_address
'Jinli Zhang'
;The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
China
;
_audit_update_record             
;
2018-04-23 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 F3 N S'
_chemical_formula_sum            'C14 H10 F3 N S'
_chemical_formula_weight         281.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H20N2O8S1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   13.5721(6)
_cell_length_b                   12.8938(8)
_cell_length_c                   7.9189(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.101(5)
_cell_angle_gamma                90
_cell_volume                     1331.42(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6110
_cell_measurement_theta_min      4.8200
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.661
_exptl_absorpt_coefficient_mu    2.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4928
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.389
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   11.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega  -28.00   31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega   75.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega    7.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega   18.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  133.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  9 omega  111.00  153.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
 11 omega   45.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega   99.00  176.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  136.0000 28

#__ type_ start__ end____ width___ exp.time_
 14 omega   80.00  160.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 80

#__ type_ start__ end____ width___ exp.time_
 15 omega   37.00   88.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0372534000
_diffrn_orient_matrix_UB_12      0.1083222000
_diffrn_orient_matrix_UB_13      -0.0372337000
_diffrn_orient_matrix_UB_21      -0.1058652000
_diffrn_orient_matrix_UB_22      0.0222737000
_diffrn_orient_matrix_UB_23      -0.1283360000
_diffrn_orient_matrix_UB_31      -0.0367870000
_diffrn_orient_matrix_UB_32      0.0455757000
_diffrn_orient_matrix_UB_33      0.1518792000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1834
_reflns_number_total             2380
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.125
_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)+(0.1080P)²+0.2845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C8-F1
 1.4 with sigma of 0.02
 C8-F3A
 1.4 with sigma of 0.02
 C8-F2
 1.4 with sigma of 0.02
 C8-F1A
 1.4 with sigma of 0.02
 C8-F3
 1.4 with sigma of 0.02
 C8-F2A
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
Uanis(F1) = Uanis(F1A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_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
C1 C 0.0486(2) 0.3498(2) -0.0225(4) 0.0486(7) Uani 1 1 d . . . . .
C2 C 0.1389(2) 0.3620(2) 0.1357(4) 0.0487(6) Uani 1 1 d . . . . .
C3 C 0.1259(2) 0.3712(2) 0.3029(4) 0.0555(7) Uani 1 1 d . . . . .
H3 H 0.0605 0.3669 0.3182 0.067 Uiso 1 1 calc R . . . .
C4 C 0.2096(3) 0.3866(3) 0.4467(5) 0.0672(9) Uani 1 1 d . . . . .
H4 H 0.2003 0.3941 0.5581 0.081 Uiso 1 1 calc R . . . .
C5 C 0.3070(3) 0.3911(3) 0.4250(5) 0.0737(10) Uani 1 1 d . . . . .
H5 H 0.3634 0.4004 0.5220 0.088 Uiso 1 1 calc R . . . .
C6 C 0.3206(3) 0.3818(3) 0.2593(5) 0.0692(9) Uani 1 1 d . . . . .
C7 C 0.2361(2) 0.3675(3) 0.1137(5) 0.0596(8) Uani 1 1 d . . . . .
H7 H 0.2452 0.3618 0.0020 0.072 Uiso 1 1 calc R . . . .
C8 C 0.4249(3) 0.3843(5) 0.2354(7) 0.1057(18) Uani 1 1 d D . . . .
C9 C -0.1218(2) 0.2653(2) -0.1235(4) 0.0508(7) Uani 1 1 d . . . . .
C10 C -0.1501(2) 0.1631(3) -0.1549(5) 0.0605(8) Uani 1 1 d . . . . .
H10 H -0.1066 0.1107 -0.0974 0.073 Uiso 1 1 calc R . . . .
C11 C -0.2426(3) 0.1388(3) -0.2713(5) 0.0719(10) Uani 1 1 d . . . . .
H11 H -0.2612 0.0696 -0.2933 0.086 Uiso 1 1 calc R . . . .
C12 C -0.3082(2) 0.2161(4) -0.3562(5) 0.0723(10) Uani 1 1 d . . . . .
H12 H -0.3706 0.1993 -0.4357 0.087 Uiso 1 1 calc R . . . .
C13 C -0.2804(3) 0.3177(3) -0.3222(6) 0.0744(10) Uani 1 1 d . . . . .
H13 H -0.3249 0.3700 -0.3773 0.089 Uiso 1 1 calc R . . . .
C14 C -0.1864(2) 0.3433(3) -0.2060(5) 0.0660(9) Uani 1 1 d . . . . .
H14 H -0.1675 0.4124 -0.1844 0.079 Uiso 1 1 calc R . . . .
F1 F 0.4319(5) 0.4048(9) 0.0773(11) 0.138(3) Uani 0.603(5) 1 d D U P A 1
F1A F 0.4939(7) 0.3682(14) 0.3824(14) 0.138(3) Uani 0.397(5) 1 d D U P A 2
F2 F 0.4660(5) 0.2841(7) 0.2581(16) 0.162(3) Uani 0.603(5) 1 d D U P A 1
F2A F 0.4442(8) 0.4928(10) 0.199(2) 0.162(3) Uani 0.397(5) 1 d D U P A 2
F3 F 0.4924(5) 0.4383(10) 0.3337(14) 0.158(3) Uani 0.603(5) 1 d D U P A 1
F3A F 0.4335(9) 0.3387(15) 0.096(2) 0.158(3) Uani 0.397(5) 1 d D U P A 2
N1 N -0.02561(18) 0.2882(2) 0.0011(4) 0.0503(6) Uani 1 1 d . . . . .
H1 H -0.011(2) 0.252(3) 0.095(5) 0.051(9) Uiso 1 1 d . . . . .
S1 S 0.04760(6) 0.40872(6) -0.20961(11) 0.0586(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.499(4) . ?
C1 N1 1.336(4) . ?
C1 S1 1.662(3) . ?
C2 C3 1.389(4) . ?
C2 C7 1.379(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(6) . ?
C6 C7 1.395(5) . ?
C6 C8 1.479(6) . ?
C7 H7 0.9300 . ?
C8 F1 1.309(8) . ?
C8 F1A 1.293(10) . ?
C8 F2 1.399(9) . ?
C8 F2A 1.466(13) . ?
C8 F3 1.239(7) . ?
C8 F3A 1.282(12) . ?
C9 C10 1.375(5) . ?
C9 C14 1.375(5) . ?
C9 N1 1.432(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(5) . ?
C14 H14 0.9300 . ?
N1 H1 0.86(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
C2 C1 S1 120.0(2) . . ?
N1 C1 C2 114.7(3) . . ?
N1 C1 S1 125.2(2) . . ?
C3 C2 C1 121.0(3) . . ?
C7 C2 C1 119.3(3) . . ?
C7 C2 C3 119.7(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 C8 120.3(4) . . ?
C7 C6 C8 119.6(4) . . ?
C2 C7 C6 119.9(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
F1 C8 C6 116.9(5) . . ?
F1 C8 F2 100.2(7) . . ?
F1A C8 C6 111.2(6) . . ?
F1A C8 F2A 101.8(8) . . ?
F2 C8 C6 109.0(5) . . ?
F2A C8 C6 106.0(5) . . ?
F3 C8 C6 119.9(6) . . ?
F3 C8 F1 104.5(7) . . ?
F3 C8 F2 103.9(8) . . ?
F3A C8 C6 114.8(6) . . ?
F3A C8 F1A 118.9(11) . . ?
F3A C8 F2A 101.9(11) . . ?
C10 C9 C14 120.4(3) . . ?
C10 C9 N1 118.5(3) . . ?
C14 C9 N1 121.0(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 119.2(4) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C1 N1 C9 127.2(3) . . ?
C1 N1 H1 116(2) . . ?
C9 N1 H1 116(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.86(4) 2.57(4) 3.379(3) 157(3) 4_566

_olex2_submission_special_instructions 'No special instructions were received'
