# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_zz
_database_code_depnum_ccdc_archive 'CCDC 1956248'
loop_
_audit_author_name
_audit_author_address
'Chuanle Zhu'
;South China University of Technology
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;
_audit_creation_date             2018-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H14 F3 N O2 S'
_chemical_formula_sum            'C15 H14 F3 N O2 S'
_chemical_formula_weight         329.33
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.516(3)
_cell_length_b                   5.6738(5)
_cell_length_c                   21.937(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.176(6)
_cell_angle_gamma                90.00
_cell_volume                     2981.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1197
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.012
_cell_measurement_theta_min      3.022
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0944 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.8634. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10820
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         3.02
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1630
_reflns_number_total             2829
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0268P)²+7.0399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C12(H12), C15(H15), C14(H14), C3(H3), C2(H2A), C1(H1)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.39458(5) 0.87249(19) 0.22976(5) 0.0274(3) Uani 1 d . . .
F1 F 0.29397(10) 0.6903(4) 0.39969(10) 0.0344(6) Uani 1 d . . .
O1 O 0.36818(12) 0.3907(5) 0.37098(11) 0.0270(7) Uani 1 d . . .
F2 F 0.31596(11) 0.4535(5) 0.48151(12) 0.0523(8) Uani 1 d . . .
F3 F 0.31820(11) 0.8278(5) 0.49629(12) 0.0563(9) Uani 1 d . . .
O2 O 0.39682(13) 0.8742(5) 0.43189(12) 0.0322(8) Uani 1 d . . .
H2 H 0.3883 0.8458 0.3921 0.048 Uiso 1 calc . . GR
N1 N 0.37336(14) 0.5577(6) 0.32543(15) 0.0241(8) Uani 1 d . . .
C5 C 0.33875(17) 0.5115(7) 0.26770(17) 0.0212(9) Uani 1 d . . .
C13 C 0.50300(17) 0.7105(7) 0.66368(18) 0.0217(9) Uani 1 d . . .
H13 H 0.5281 0.7205 0.7072 0.026 Uiso 1 calc . . R
C4 C 0.34135(16) 0.6674(7) 0.21601(17) 0.0200(9) Uani 1 d . . .
C11 C 0.46423(16) 0.8752(7) 0.55664(17) 0.0198(9) Uani 1 d . . .
H11 H 0.4631 0.9988 0.5270 0.024 Uiso 1 calc . . R
C10 C 0.42941(17) 0.6819(7) 0.53574(17) 0.0209(9) Uani 1 d . . .
C12 C 0.50076(16) 0.8905(7) 0.62041(18) 0.0220(9) Uani 1 d . . .
H12 H 0.5242 1.0246 0.6342 0.026 Uiso 1 calc . . R
C8 C 0.39064(17) 0.6648(7) 0.46485(17) 0.0212(9) Uani 1 d . . .
C15 C 0.43173(17) 0.5011(7) 0.57998(17) 0.0228(9) Uani 1 d . . .
H15 H 0.4080 0.3679 0.5665 0.027 Uiso 1 calc . . R
C14 C 0.46866(17) 0.5154(7) 0.64361(18) 0.0226(9) Uani 1 d . . .
H14 H 0.4703 0.3914 0.6733 0.027 Uiso 1 calc . . R
C3 C 0.30497(17) 0.6812(7) 0.15350(18) 0.0259(10) Uani 1 d . . .
H3 H 0.2732 0.5826 0.1366 0.031 Uiso 1 calc . . R
C6 C 0.29720(17) 0.3135(7) 0.25293(18) 0.0271(10) Uani 1 d . . .
H6A H 0.3159 0.1686 0.2737 0.041 Uiso 1 calc . . GR
H6B H 0.2813 0.2901 0.2058 0.041 Uiso 1 calc . . GR
H6C H 0.2673 0.3526 0.2697 0.041 Uiso 1 calc . . GR
C2 C 0.31960(18) 0.8576(8) 0.11662(19) 0.0288(10) Uani 1 d . . .
H2A H 0.2987 0.8904 0.0724 0.035 Uiso 1 calc . . R
C7 C 0.40616(18) 0.4464(7) 0.43418(17) 0.0258(10) Uani 1 d . . .
H7A H 0.4437 0.4703 0.4315 0.031 Uiso 1 calc . . R
H7B H 0.4084 0.3100 0.4631 0.031 Uiso 1 calc . . R
C9 C 0.32986(19) 0.6608(8) 0.4603(2) 0.0340(11) Uani 1 d . . .
C1 C 0.36678(18) 0.9745(7) 0.15130(19) 0.0279(10) Uani 1 d . . .
H1 H 0.3827 1.0984 0.1343 0.033 Uiso 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 C4 1.734(4) . ?
S1 C1 1.720(4) . ?
F1 C9 1.339(5) . ?
O1 N1 1.416(4) . ?
O1 C7 1.426(4) . ?
F2 C9 1.356(5) . ?
F3 C9 1.332(5) . ?
O2 H2 0.8400 . ?
O2 C8 1.427(4) . ?
N1 C5 1.297(5) . ?
C5 C4 1.458(5) . ?
C5 C6 1.501(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.382(5) . ?
C13 C14 1.386(5) . ?
C4 C3 1.367(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(5) . ?
C11 C12 1.391(5) . ?
C10 C8 1.531(5) . ?
C10 C15 1.399(5) . ?
C12 H12 0.9500 . ?
C8 C7 1.526(5) . ?
C8 C9 1.519(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(5) . ?
C14 H14 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.415(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C2 H2A 0.9500 . ?
C2 C1 1.355(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 H1 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
C1 S1 C4 91.4(2) . . ?
N1 O1 C7 109.9(3) . . ?
C8 O2 H2 109.5 . . ?
C5 N1 O1 110.9(3) . . ?
N1 C5 C4 116.0(4) . . ?
N1 C5 C6 123.7(3) . . ?
C4 C5 C6 120.3(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C5 C4 S1 121.0(3) . . ?
C3 C4 S1 110.9(3) . . ?
C3 C4 C5 128.1(4) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C10 C8 120.1(3) . . ?
C11 C10 C15 118.8(4) . . ?
C15 C10 C8 121.1(3) . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
O2 C8 C10 108.4(3) . . ?
O2 C8 C7 111.2(3) . . ?
O2 C8 C9 105.5(3) . . ?
C7 C8 C10 108.9(3) . . ?
C9 C8 C10 110.8(3) . . ?
C9 C8 C7 111.9(3) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C4 C3 H3 123.5 . . ?
C4 C3 C2 113.1(4) . . ?
C2 C3 H3 123.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C2 H2A 123.7 . . ?
C1 C2 C3 112.5(4) . . ?
C1 C2 H2A 123.7 . . ?
O1 C7 C8 114.6(3) . . ?
O1 C7 H7A 108.6 . . ?
O1 C7 H7B 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
F1 C9 F2 106.2(4) . . ?
F1 C9 C8 113.4(3) . . ?
F2 C9 C8 111.9(4) . . ?
F3 C9 F1 106.5(3) . . ?
F3 C9 F2 105.9(3) . . ?
F3 C9 C8 112.4(4) . . ?
S1 C1 H1 123.9 . . ?
C2 C1 S1 112.2(3) . . ?
C2 C1 H1 123.9 . . ?

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
O2 H2 N1 0.84 2.14 2.841(4) 141.2 .


_olex2_submission_special_instructions 'No special instructions were received'
