# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_xb2406_0m
_database_code_depnum_ccdc_archive 'CCDC 1976664'
loop_
_audit_author_name
_audit_author_address
'mengyue wang'
;Northwest University
China
;
_audit_update_record             
;
2020-01-10 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H9 F3 O3 S'
_chemical_formula_sum            'C10 H9 F3 O3 S'
_chemical_formula_weight         266.23
_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'
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'
F F 0.0171 0.0103 '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                   4.8370(16)
_cell_length_b                   12.644(4)
_cell_length_c                   18.820(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.700(6)
_cell_angle_gamma                90
_cell_volume                     1150.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1057
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.21
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0859 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.8485.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.099
_diffrn_reflns_theta_min         1.941
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1409
_reflns_number_total             2259
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.013
_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)+(0.0543P)²+0.1915P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1315
_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:
 C1(H1), C3(H3), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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 1.12441(19) 0.47355(6) 0.17510(5) 0.0721(3) Uani 1 1 d . . . . .
O1 O 0.9978(5) 0.27883(15) 0.21219(11) 0.0726(6) Uani 1 1 d . . . . .
O2 O 0.2898(4) 0.30731(14) 0.40885(10) 0.0645(6) Uani 1 1 d . . . . .
O3 O 0.2549(4) 0.50391(14) 0.43690(10) 0.0588(5) Uani 1 1 d . . . . .
C1 C 0.6290(6) 0.3378(2) 0.31904(14) 0.0525(7) Uani 1 1 d . . . . .
H1 H 0.6433 0.2660 0.3089 0.063 Uiso 1 1 calc R . . . .
C2 C 0.9610(6) 0.3700(2) 0.22577(14) 0.0530(7) Uani 1 1 d . . . . .
C3 C 0.7671(6) 0.5169(2) 0.29808(14) 0.0540(7) Uani 1 1 d . . . . .
H3 H 0.8730 0.5657 0.2738 0.065 Uiso 1 1 calc R . . . .
C4 C 0.7863(6) 0.41095(19) 0.28211(14) 0.0480(6) Uani 1 1 d . . . . .
C5 C 0.4330(6) 0.4799(2) 0.38581(14) 0.0489(7) Uani 1 1 d . . . . .
C6 C 0.4538(6) 0.3714(2) 0.37007(14) 0.0507(7) Uani 1 1 d . . . . .
C7 C 0.5915(6) 0.5514(2) 0.34988(15) 0.0537(7) Uani 1 1 d . . . . .
H7 H 0.5806 0.6231 0.3605 0.064 Uiso 1 1 calc R . . . .
F1 F 1.3657(5) 0.46456(16) 0.05943(12) 0.1205(9) Uani 1 1 d . . . . .
F2 F 1.0602(5) 0.34555(19) 0.06791(11) 0.1187(9) Uani 1 1 d . . . . .
F3 F 1.4436(5) 0.32915(18) 0.12370(14) 0.1171(9) Uani 1 1 d . . . . .
C8 C 0.2954(8) 0.1981(2) 0.39434(18) 0.0938(13) Uani 1 1 d . . . . .
H8A H 0.2452 0.1863 0.3453 0.141 Uiso 1 1 calc GR . . . .
H8B H 0.1666 0.1623 0.4239 0.141 Uiso 1 1 calc GR . . . .
H8C H 0.4783 0.1712 0.4040 0.141 Uiso 1 1 calc GR . . . .
C9 C 0.2199(7) 0.6136(2) 0.45404(16) 0.0677(9) Uani 1 1 d . . . . .
H9A H 0.1591 0.6515 0.4122 0.101 Uiso 1 1 calc GR . . . .
H9B H 0.3929 0.6423 0.4714 0.101 Uiso 1 1 calc GR . . . .
H9C H 0.0843 0.6205 0.4900 0.101 Uiso 1 1 calc GR . . . .
C10 C 1.2511(8) 0.3989(3) 0.10373(19) 0.0778(10) 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
S1 C2 1.815(3) . ?
S1 C10 1.766(3) . ?
O1 C2 1.195(3) . ?
O2 C6 1.361(3) . ?
O2 C8 1.408(4) . ?
O3 C5 1.345(3) . ?
O3 C9 1.436(3) . ?
C1 C4 1.396(4) . ?
C1 C6 1.367(4) . ?
C2 C4 1.470(4) . ?
C3 C4 1.377(4) . ?
C3 C7 1.382(4) . ?
C5 C6 1.408(4) . ?
C5 C7 1.375(4) . ?
F1 C10 1.311(3) . ?
F2 C10 1.313(4) . ?
F3 C10 1.329(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
C10 S1 C2 100.39(14) . . ?
C6 O2 C8 117.7(2) . . ?
C5 O3 C9 117.5(2) . . ?
C6 C1 C4 120.1(2) . . ?
O1 C2 S1 120.9(2) . . ?
O1 C2 C4 125.9(2) . . ?
C4 C2 S1 113.17(19) . . ?
C4 C3 C7 120.5(3) . . ?
C1 C4 C2 117.3(2) . . ?
C3 C4 C1 119.7(3) . . ?
C3 C4 C2 123.0(2) . . ?
O3 C5 C6 114.9(2) . . ?
O3 C5 C7 125.6(2) . . ?
C7 C5 C6 119.5(3) . . ?
O2 C6 C1 125.1(2) . . ?
O2 C6 C5 114.9(2) . . ?
C1 C6 C5 120.0(2) . . ?
C5 C7 C3 120.2(2) . . ?
F1 C10 S1 108.0(2) . . ?
F1 C10 F3 107.1(3) . . ?
F2 C10 S1 114.2(3) . . ?
F2 C10 F1 107.6(3) . . ?
F2 C10 F3 106.3(3) . . ?
F3 C10 S1 113.3(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
