# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_d8v21849_0m
_database_code_depnum_ccdc_archive 'CCDC 2236643'
loop_
_audit_author_name
_audit_author_address
'Huiyu Chen'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 F3 N O2 S'
_chemical_formula_weight         353.35

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   9.3303(17)
_cell_length_b                   17.815(3)
_cell_length_c                   10.8360(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.207(5)
_cell_angle_gamma                90
_cell_volume                     1667.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7762
_cell_measurement_theta_min      4.660
_cell_measurement_theta_max      54.712

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5367
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15324
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.058
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3088
_reflns_number_gt                2432
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0738P)²+0.9695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3088
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.67854(8) 0.50317(4) 0.27445(7) 0.0420(3) Uani 1 1 d . . . . .
F1 F 0.3944(2) 0.55965(12) 0.1750(2) 0.0807(7) Uani 1 1 d . . . . .
F2 F 0.4862(3) 0.54441(14) 0.3866(3) 0.0906(8) Uani 1 1 d . . . . .
F3 F 0.5688(3) 0.63329(11) 0.2985(3) 0.0907(8) Uani 1 1 d . . . . .
O1 O 0.6011(2) 0.29049(11) 0.2792(2) 0.0483(5) Uani 1 1 d . . . . .
O2 O 0.6838(3) 0.52251(13) 0.1437(2) 0.0585(6) Uani 1 1 d . . . . .
N1 N 0.4836(3) 0.30664(14) 0.1447(2) 0.0478(6) Uani 1 1 d . . . . .
C1 C 0.4461(3) 0.38727(16) 0.1513(3) 0.0411(6) Uani 1 1 d . . . . .
H1 H 0.4326 0.4123 0.0671 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5895(3) 0.41608(15) 0.2615(3) 0.0377(6) Uani 1 1 d . . . . .
C3 C 0.6669(3) 0.35705(15) 0.3331(3) 0.0405(6) Uani 1 1 d . . . . .
C4 C 0.8036(3) 0.35035(16) 0.4567(3) 0.0421(6) Uani 1 1 d . . . . .
C5 C 0.8313(4) 0.40244(18) 0.5585(3) 0.0524(8) Uani 1 1 d . . . . .
H5 H 0.7635 0.4424 0.5477 0.063 Uiso 1 1 calc R U . . .
C6 C 0.9585(4) 0.3952(2) 0.6753(4) 0.0697(10) Uani 1 1 d . . . . .
H6 H 0.9762 0.4305 0.7429 0.084 Uiso 1 1 calc R U . . .
C7 C 1.0594(4) 0.3367(2) 0.6930(4) 0.0727(11) Uani 1 1 d . . . . .
H7 H 1.1446 0.3319 0.7726 0.087 Uiso 1 1 calc R U . . .
C8 C 1.0347(4) 0.2852(2) 0.5937(4) 0.0675(10) Uani 1 1 d . . . . .
H8 H 1.1045 0.2460 0.6051 0.081 Uiso 1 1 calc R U . . .
C9 C 0.9067(4) 0.29092(18) 0.4764(4) 0.0566(8) Uani 1 1 d . . . . .
H9 H 0.8893 0.2549 0.4102 0.068 Uiso 1 1 calc R U . . .
C10 C 0.2989(3) 0.39370(16) 0.1797(3) 0.0408(6) Uani 1 1 d . . . . .
C11 C 0.1623(3) 0.41363(18) 0.0811(3) 0.0540(8) Uani 1 1 d . . . . .
H11 H 0.1606 0.4255 -0.0030 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0252(4) 0.4166(2) 0.1042(5) 0.0716(11) Uani 1 1 d . . . . .
H12 H -0.0672 0.4300 0.0362 0.086 Uiso 1 1 calc R U . . .
C13 C 0.0284(4) 0.3995(2) 0.2280(5) 0.0693(10) Uani 1 1 d . . . . .
H13 H -0.0627 0.4010 0.2440 0.083 Uiso 1 1 calc R U . . .
C14 C 0.1633(4) 0.3803(2) 0.3280(4) 0.0699(10) Uani 1 1 d . . . . .
H14 H 0.1641 0.3694 0.4122 0.084 Uiso 1 1 calc R U . . .
C15 C 0.2992(4) 0.3769(2) 0.3054(3) 0.0578(8) Uani 1 1 d . . . . .
H15 H 0.3911 0.3634 0.3741 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5210(4) 0.56307(18) 0.2825(4) 0.0568(8) Uani 1 1 d . . . . .
C17 C 0.5660(5) 0.2938(2) 0.0544(4) 0.0722(11) Uani 1 1 d . . . . .
H17A H 0.6501 0.3288 0.0748 0.108 Uiso 1 1 calc R U . . .
H17B H 0.4958 0.3008 -0.0361 0.108 Uiso 1 1 calc R U . . .
H17C H 0.6058 0.2435 0.0658 0.108 Uiso 1 1 calc R U . . .


_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 O2 1.477(2) . ?
S1 C2 1.740(3) . ?
S1 C16 1.845(3) . ?
F1 C16 1.310(4) . ?
F2 C16 1.328(4) . ?
F3 C16 1.317(4) . ?
O1 C3 1.361(3) . ?
O1 N1 1.484(3) . ?
N1 C17 1.473(4) . ?
N1 C1 1.486(4) . ?
C1 C2 1.507(4) . ?
C1 C10 1.521(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.344(4) . ?
C3 C4 1.464(4) . ?
C4 C5 1.389(4) . ?
C4 C9 1.392(4) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.365(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.394(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O2 S1 C2 108.60(13) . . ?
O2 S1 C16 103.09(15) . . ?
C2 S1 C16 98.90(14) . . ?
C3 O1 N1 107.4(2) . . ?
C17 N1 O1 104.2(2) . . ?
C17 N1 C1 111.9(3) . . ?
O1 N1 C1 103.89(19) . . ?
N1 C1 C2 102.3(2) . . ?
N1 C1 C10 109.2(2) . . ?
C2 C1 C10 114.4(2) . . ?
N1 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
C10 C1 H1 110.2 . . ?
C3 C2 C1 108.3(2) . . ?
C3 C2 S1 121.0(2) . . ?
C1 C2 S1 128.4(2) . . ?
C2 C3 O1 112.2(2) . . ?
C2 C3 C4 133.2(3) . . ?
O1 C3 C4 114.6(2) . . ?
C5 C4 C9 118.4(3) . . ?
C5 C4 C3 120.6(3) . . ?
C9 C4 C3 121.0(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C1 120.6(3) . . ?
C15 C10 C1 120.9(3) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
F1 C16 F3 107.9(3) . . ?
F1 C16 F2 108.4(3) . . ?
F3 C16 F2 107.8(3) . . ?
F1 C16 S1 113.4(2) . . ?
F3 C16 S1 108.6(2) . . ?
F2 C16 S1 110.5(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C3 O1 N1 C17 95.1(3) . . . . ?
C3 O1 N1 C1 -22.2(3) . . . . ?
C17 N1 C1 C2 -88.1(3) . . . . ?
O1 N1 C1 C2 23.7(2) . . . . ?
C17 N1 C1 C10 150.4(3) . . . . ?
O1 N1 C1 C10 -97.8(2) . . . . ?
N1 C1 C2 C3 -18.4(3) . . . . ?
C10 C1 C2 C3 99.5(3) . . . . ?
N1 C1 C2 S1 144.0(2) . . . . ?
C10 C1 C2 S1 -98.1(3) . . . . ?
O2 S1 C2 C3 116.8(2) . . . . ?
C16 S1 C2 C3 -136.1(2) . . . . ?
O2 S1 C2 C1 -43.6(3) . . . . ?
C16 S1 C2 C1 63.5(3) . . . . ?
C1 C2 C3 O1 5.0(3) . . . . ?
S1 C2 C3 O1 -158.98(19) . . . . ?
C1 C2 C3 C4 -173.5(3) . . . . ?
S1 C2 C3 C4 22.5(4) . . . . ?
N1 O1 C3 C2 11.0(3) . . . . ?
N1 O1 C3 C4 -170.2(2) . . . . ?
C2 C3 C4 C5 35.0(4) . . . . ?
O1 C3 C4 C5 -143.5(3) . . . . ?
C2 C3 C4 C9 -146.5(3) . . . . ?
O1 C3 C4 C9 35.1(4) . . . . ?
C9 C4 C5 C6 0.4(5) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C7 C8 C9 -1.4(6) . . . . ?
C7 C8 C9 C4 1.7(5) . . . . ?
C5 C4 C9 C8 -1.2(5) . . . . ?
C3 C4 C9 C8 -179.7(3) . . . . ?
N1 C1 C10 C11 -105.2(3) . . . . ?
C2 C1 C10 C11 140.9(3) . . . . ?
N1 C1 C10 C15 72.5(3) . . . . ?
C2 C1 C10 C15 -41.4(4) . . . . ?
C15 C10 C11 C12 -0.6(5) . . . . ?
C1 C10 C11 C12 177.2(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C14 0.4(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C10 0.4(6) . . . . ?
C11 C10 C15 C14 0.3(5) . . . . ?
C1 C10 C15 C14 -177.5(3) . . . . ?
O2 S1 C16 F1 49.0(3) . . . . ?
C2 S1 C16 F1 -62.6(3) . . . . ?
O2 S1 C16 F3 -71.0(3) . . . . ?
C2 S1 C16 F3 177.4(2) . . . . ?
O2 S1 C16 F2 171.0(2) . . . . ?
C2 S1 C16 F2 59.4(3) . . . . ?

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
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665
C1 H1 O2 0.98 2.42 3.367(3) 161.8 3_665

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v22526_0m
_database_code_depnum_ccdc_archive 'CCDC 2236659'
loop_
_audit_author_name
_audit_author_address
'Huiyu Chen'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 F3 N O2 S'
_chemical_formula_weight         367.38

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8704(3)
_cell_length_b                   16.8650(5)
_cell_length_c                   11.3723(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.3140(10)
_cell_angle_gamma                90
_cell_volume                     1711.30(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      4.640
_cell_measurement_theta_max      54.913

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5204
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21017
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.583
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3315
_reflns_number_gt                3012
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.6854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.85186(4) 0.46334(2) 0.53276(4) 0.02939(13) Uani 1 1 d . . . . .
F1 F 0.78229(15) 0.34167(8) 0.64864(13) 0.0662(4) Uani 1 1 d . . . . .
F2 F 0.80038(18) 0.45456(9) 0.73767(13) 0.0789(4) Uani 1 1 d . . . . .
F3 F 0.60880(13) 0.42692(10) 0.56078(14) 0.0753(4) Uani 1 1 d . . . . .
O1 O 0.64868(12) 0.33153(6) 0.22039(10) 0.0353(3) Uani 1 1 d . . . . .
O2 O 1.01183(12) 0.44704(7) 0.61751(11) 0.0386(3) Uani 1 1 d . . . . .
N1 N 0.74953(15) 0.26979(7) 0.30665(14) 0.0364(3) Uani 1 1 d . . . . .
C1 C 0.67524(17) 0.40050(8) 0.29077(14) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.79254(16) 0.39375(8) 0.40680(14) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.86939(16) 0.31466(8) 0.41295(15) 0.0302(3) Uani 1 1 d . . . . .
H3 H 0.8937 0.2886 0.4976 0.036 Uiso 1 1 calc R U . . .
C4 C 1.00908(17) 0.32135(8) 0.38961(15) 0.0314(3) Uani 1 1 d . . . . .
C5 C 1.14949(18) 0.30951(10) 0.48965(17) 0.0382(4) Uani 1 1 d . . . . .
H5 H 1.1586 0.2972 0.5733 0.046 Uiso 1 1 calc R U . . .
C6 C 1.2773(2) 0.31561(11) 0.4683(2) 0.0483(4) Uani 1 1 d . . . . .
H6 H 1.3722 0.3076 0.5373 0.058 Uiso 1 1 calc R U . . .
C7 C 1.2654(2) 0.33338(13) 0.3463(2) 0.0580(5) Uani 1 1 d . . . . .
H7 H 1.3519 0.3379 0.3318 0.070 Uiso 1 1 calc R U . . .
C8 C 1.1260(3) 0.34448(16) 0.2458(2) 0.0681(7) Uani 1 1 d . . . . .
H8 H 1.1173 0.3564 0.1621 0.082 Uiso 1 1 calc R U . . .
C9 C 0.9982(2) 0.33826(13) 0.26693(19) 0.0530(5) Uani 1 1 d . . . . .
H9 H 0.9034 0.3456 0.1974 0.064 Uiso 1 1 calc R U . . .
C10 C 0.57236(16) 0.46548(8) 0.22218(14) 0.0279(3) Uani 1 1 d . . . . .
C11 C 0.62035(18) 0.54408(9) 0.24704(16) 0.0332(3) Uani 1 1 d . . . . .
H11 H 0.7180 0.5561 0.3086 0.040 Uiso 1 1 calc R U . . .
C12 C 0.52243(19) 0.60410(9) 0.17995(16) 0.0380(4) Uani 1 1 d . . . . .
H12 H 0.5535 0.6572 0.1968 0.046 Uiso 1 1 calc R U . . .
C13 C 0.37939(19) 0.58673(9) 0.08841(16) 0.0356(4) Uani 1 1 d . . . . .
H13 H 0.3145 0.6284 0.0436 0.043 Uiso 1 1 calc R U . . .
C14 C 0.32951(17) 0.50893(9) 0.06121(14) 0.0308(3) Uani 1 1 d . . . . .
C15 C 0.42808(17) 0.44872(9) 0.12938(14) 0.0291(3) Uani 1 1 d . . . . .
H15 H 0.3966 0.3956 0.1124 0.035 Uiso 1 1 calc R U . . .
C16 C 0.17345(19) 0.49064(11) -0.03825(17) 0.0423(4) Uani 1 1 d . . . . .
H16A H 0.1728 0.4866 -0.1236 0.063 Uiso 1 1 calc R U . . .
H16B H 0.1062 0.5327 -0.0388 0.063 Uiso 1 1 calc R U . . .
H16C H 0.1406 0.4408 -0.0166 0.063 Uiso 1 1 calc R U . . .
C17 C 0.7546(2) 0.41812(12) 0.62479(18) 0.0440(4) Uani 1 1 d . . . . .
C18 C 0.6553(2) 0.22520(11) 0.3530(2) 0.0534(5) Uani 1 1 d . . . . .
H18A H 0.6191 0.2603 0.4009 0.080 Uiso 1 1 calc R U . . .
H18B H 0.7133 0.1827 0.4095 0.080 Uiso 1 1 calc R U . . .
H18C H 0.5707 0.2030 0.2793 0.080 Uiso 1 1 calc R U . . .


_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 O2 1.4819(12) . ?
S1 C2 1.7479(15) . ?
S1 C17 1.8593(18) . ?
F1 C17 1.322(2) . ?
F2 C17 1.317(2) . ?
F3 C17 1.314(2) . ?
O1 C1 1.3721(17) . ?
O1 N1 1.4840(15) . ?
N1 C18 1.459(2) . ?
N1 C3 1.4868(19) . ?
C1 C2 1.337(2) . ?
C1 C10 1.471(2) . ?
C2 C3 1.5212(19) . ?
C3 C4 1.516(2) . ?
C3 H3 0.9900 . ?
C4 C5 1.381(2) . ?
C4 C9 1.382(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.374(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.376(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C15 1.392(2) . ?
C10 C11 1.395(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.391(2) . ?
C14 C16 1.502(2) . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?

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
O2 S1 C2 107.38(7) . . ?
O2 S1 C17 102.75(8) . . ?
C2 S1 C17 96.50(8) . . ?
C1 O1 N1 107.60(10) . . ?
C18 N1 O1 104.44(12) . . ?
C18 N1 C3 112.17(14) . . ?
O1 N1 C3 104.83(10) . . ?
C2 C1 O1 111.86(12) . . ?
C2 C1 C10 134.17(13) . . ?
O1 C1 C10 113.95(12) . . ?
C1 C2 C3 108.92(12) . . ?
C1 C2 S1 126.65(11) . . ?
C3 C2 S1 124.43(11) . . ?
N1 C3 C4 111.27(13) . . ?
N1 C3 C2 101.60(11) . . ?
C4 C3 C2 113.56(12) . . ?
N1 C3 H3 110.0 . . ?
C4 C3 H3 110.0 . . ?
C2 C3 H3 110.0 . . ?
C5 C4 C9 118.61(16) . . ?
C5 C4 C3 120.84(14) . . ?
C9 C4 C3 120.54(14) . . ?
C4 C5 C6 120.83(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.13(17) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.47(19) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 120.49(18) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C15 C10 C11 119.69(14) . . ?
C15 C10 C1 120.09(13) . . ?
C11 C10 C1 120.19(13) . . ?
C12 C11 C10 119.16(14) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 120.61(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.27(14) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 117.96(14) . . ?
C13 C14 C16 120.88(14) . . ?
C15 C14 C16 121.16(14) . . ?
C14 C15 C10 121.31(14) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F3 C17 F2 108.97(16) . . ?
F3 C17 F1 107.76(16) . . ?
F2 C17 F1 107.49(16) . . ?
F3 C17 S1 110.40(13) . . ?
F2 C17 S1 108.23(13) . . ?
F1 C17 S1 113.86(13) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C1 O1 N1 C18 98.93(15) . . . . ?
C1 O1 N1 C3 -19.19(16) . . . . ?
N1 O1 C1 C2 7.26(17) . . . . ?
N1 O1 C1 C10 -174.08(12) . . . . ?
O1 C1 C2 C3 7.68(18) . . . . ?
C10 C1 C2 C3 -170.61(16) . . . . ?
O1 C1 C2 S1 -172.64(11) . . . . ?
C10 C1 C2 S1 9.1(3) . . . . ?
O2 S1 C2 C1 -158.30(14) . . . . ?
C17 S1 C2 C1 96.13(15) . . . . ?
O2 S1 C2 C3 21.34(14) . . . . ?
C17 S1 C2 C3 -84.23(14) . . . . ?
C18 N1 C3 C4 148.16(14) . . . . ?
O1 N1 C3 C4 -99.10(13) . . . . ?
C18 N1 C3 C2 -90.65(15) . . . . ?
O1 N1 C3 C2 22.08(15) . . . . ?
C1 C2 C3 N1 -18.94(16) . . . . ?
S1 C2 C3 N1 161.37(11) . . . . ?
C1 C2 C3 C4 100.63(15) . . . . ?
S1 C2 C3 C4 -79.06(16) . . . . ?
N1 C3 C4 C5 -136.43(14) . . . . ?
C2 C3 C4 C5 109.66(16) . . . . ?
N1 C3 C4 C9 42.6(2) . . . . ?
C2 C3 C4 C9 -71.34(19) . . . . ?
C9 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C6 179.99(15) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C5 C4 C9 C8 -1.1(3) . . . . ?
C3 C4 C9 C8 179.90(19) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C2 C1 C10 C15 -153.47(17) . . . . ?
O1 C1 C10 C15 28.3(2) . . . . ?
C2 C1 C10 C11 28.4(3) . . . . ?
O1 C1 C10 C11 -149.84(14) . . . . ?
C15 C10 C11 C12 0.9(2) . . . . ?
C1 C10 C11 C12 179.02(15) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C12 C13 C14 C16 179.79(16) . . . . ?
C13 C14 C15 C10 0.0(2) . . . . ?
C16 C14 C15 C10 -179.57(14) . . . . ?
C11 C10 C15 C14 -0.6(2) . . . . ?
C1 C10 C15 C14 -178.70(14) . . . . ?
O2 S1 C17 F3 -179.33(13) . . . . ?
C2 S1 C17 F3 -69.82(15) . . . . ?
O2 S1 C17 F2 61.47(15) . . . . ?
C2 S1 C17 F2 170.99(14) . . . . ?
O2 S1 C17 F1 -57.98(15) . . . . ?
C2 S1 C17 F1 51.54(15) . . . . ?

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
C3 H3 F1 0.99 2.56 3.178(2) 120.1 .
C3 H3 F1 0.99 2.56 3.178(2) 120.1 .
C3 H3 F1 0.99 2.56 3.178(2) 120.1 .
C3 H3 F1 0.99 2.56 3.178(2) 120.1 .

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v22527_0m
_database_code_depnum_ccdc_archive 'CCDC 2236666'
loop_
_audit_author_name
_audit_author_address
'Huiyu Chen'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 F3 N O2 S'
_chemical_formula_weight         367.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9764(5)
_cell_length_b                   9.7004(6)
_cell_length_c                   10.5392(6)
_cell_angle_alpha                102.617(2)
_cell_angle_beta                 92.927(2)
_cell_angle_gamma                99.557(2)
_cell_volume                     879.46(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      4.376
_cell_measurement_theta_max      55.040

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5644
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18169
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.183
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3391
_reflns_number_gt                3128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+0.2614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3391
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.18775(4) 0.31515(4) 0.87182(3) 0.03161(14) Uani 1 1 d . . . . .
F1 F 0.35629(12) 0.16210(13) 0.97935(11) 0.0538(3) Uani 1 1 d . . . . .
F2 F 0.12583(13) 0.14435(12) 1.02680(11) 0.0539(3) Uani 1 1 d . . . . .
F3 F 0.17587(16) 0.03661(11) 0.83763(12) 0.0626(3) Uani 1 1 d . . . . .
O1 O 0.41225(12) 0.36692(12) 0.57728(10) 0.0355(3) Uani 1 1 d . . . . .
O2 O 0.25110(14) 0.43458(12) 0.98451(11) 0.0440(3) Uani 1 1 d . . . . .
N1 N 0.53700(14) 0.42311(14) 0.68413(12) 0.0345(3) Uani 1 1 d . . . . .
C1 C 0.28542(17) 0.32062(15) 0.63259(14) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.31839(16) 0.30841(15) 0.75564(14) 0.0305(3) Uani 1 1 d . . . . .
C3 C 0.48967(16) 0.34109(15) 0.78384(14) 0.0311(3) Uani 1 1 d . . . . .
H3 H 0.5181 0.4031 0.8725 0.037 Uiso 1 1 calc R U . . .
C4 C 0.56326(17) 0.20930(16) 0.76840(15) 0.0323(3) Uani 1 1 d . . . . .
C5 C 0.50157(19) 0.08111(18) 0.68150(16) 0.0399(4) Uani 1 1 d . . . . .
H5 H 0.4093 0.0736 0.6319 0.048 Uiso 1 1 calc R U . . .
C6 C 0.5737(2) -0.03650(18) 0.66651(17) 0.0459(4) Uani 1 1 d . . . . .
H6 H 0.5307 -0.1227 0.6066 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7081(2) -0.02700(19) 0.73933(19) 0.0479(4) Uani 1 1 d . . . . .
H7 H 0.7576 -0.1063 0.7292 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7698(2) 0.0998(2) 0.8274(2) 0.0497(4) Uani 1 1 d . . . . .
H8 H 0.8610 0.1061 0.8780 0.060 Uiso 1 1 calc R U . . .
C9 C 0.69847(19) 0.21795(18) 0.84202(18) 0.0419(4) Uani 1 1 d . . . . .
H9 H 0.7418 0.3040 0.9019 0.050 Uiso 1 1 calc R U . . .
C10 C 0.14401(18) 0.29245(16) 0.54841(14) 0.0333(3) Uani 1 1 d . . . . .
C11 C 0.0187(2) 0.19587(18) 0.56820(17) 0.0442(4) Uani 1 1 d . . . . .
H11 H 0.0256 0.1444 0.6336 0.053 Uiso 1 1 calc R U . . .
C12 C -0.1157(2) 0.1764(2) 0.4908(2) 0.0548(5) Uani 1 1 d . . . . .
H12 H -0.2021 0.1152 0.5064 0.066 Uiso 1 1 calc R U . . .
C13 C -0.1232(2) 0.2470(2) 0.39061(18) 0.0521(5) Uani 1 1 d . . . . .
H13 H -0.2147 0.2315 0.3378 0.062 Uiso 1 1 calc R U . . .
C14 C 0.0011(2) 0.34001(18) 0.36609(16) 0.0422(4) Uani 1 1 d . . . . .
C15 C 0.13404(19) 0.36416(17) 0.44747(15) 0.0366(3) Uani 1 1 d . . . . .
H15 H 0.2184 0.4296 0.4345 0.044 Uiso 1 1 calc R U . . .
C16 C -0.0053(3) 0.4150(3) 0.25536(19) 0.0591(5) Uani 1 1 d . . . . .
H16A H 0.0450 0.5144 0.2851 0.089 Uiso 1 1 calc R U . . .
H16B H -0.1104 0.4113 0.2259 0.089 Uiso 1 1 calc R U . . .
H16C H 0.0453 0.3675 0.1838 0.089 Uiso 1 1 calc R U . . .
C17 C 0.2156(2) 0.15427(18) 0.93145(16) 0.0396(4) Uani 1 1 d . . . . .
C18 C 0.5275(2) 0.57519(17) 0.72978(17) 0.0411(4) Uani 1 1 d . . . . .
H18A H 0.5334 0.6212 0.6568 0.062 Uiso 1 1 calc R U . . .
H18B H 0.6109 0.6219 0.7954 0.062 Uiso 1 1 calc R U . . .
H18C H 0.4320 0.5831 0.7674 0.062 Uiso 1 1 calc R U . . .


_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 O2 1.4790(11) . ?
S1 C2 1.7366(15) . ?
S1 C17 1.8534(17) . ?
F1 C17 1.320(2) . ?
F2 C17 1.329(2) . ?
F3 C17 1.320(2) . ?
O1 C1 1.3601(18) . ?
O1 N1 1.4898(16) . ?
N1 C18 1.467(2) . ?
N1 C3 1.4887(19) . ?
C1 C2 1.350(2) . ?
C1 C10 1.462(2) . ?
C2 C3 1.518(2) . ?
C3 C4 1.516(2) . ?
C3 H3 0.9900 . ?
C4 C5 1.383(2) . ?
C4 C9 1.387(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C11 1.395(2) . ?
C10 C15 1.399(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.389(2) . ?
C14 C16 1.507(3) . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?

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
O2 S1 C2 107.94(7) . . ?
O2 S1 C17 102.81(7) . . ?
C2 S1 C17 98.91(7) . . ?
C1 O1 N1 107.33(10) . . ?
C18 N1 C3 110.91(12) . . ?
C18 N1 O1 104.34(11) . . ?
C3 N1 O1 102.90(10) . . ?
C2 C1 O1 111.76(13) . . ?
C2 C1 C10 133.29(14) . . ?
O1 C1 C10 114.94(13) . . ?
C1 C2 C3 107.88(13) . . ?
C1 C2 S1 123.06(11) . . ?
C3 C2 S1 125.78(11) . . ?
N1 C3 C4 110.46(12) . . ?
N1 C3 C2 101.88(11) . . ?
C4 C3 C2 114.41(12) . . ?
N1 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
C5 C4 C9 118.74(15) . . ?
C5 C4 C3 122.22(14) . . ?
C9 C4 C3 119.03(14) . . ?
C4 C5 C6 121.01(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 119.96(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 119.52(16) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.68(17) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 120.08(16) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C15 119.69(15) . . ?
C11 C10 C1 120.78(14) . . ?
C15 C10 C1 119.53(15) . . ?
C12 C11 C10 119.46(17) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.06(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 121.63(16) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 118.19(16) . . ?
C13 C14 C16 121.91(17) . . ?
C15 C14 C16 119.90(18) . . ?
C14 C15 C10 120.88(16) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 C17 F3 109.34(15) . . ?
F1 C17 F2 107.83(13) . . ?
F3 C17 F2 108.18(14) . . ?
F1 C17 S1 112.93(12) . . ?
F3 C17 S1 110.81(11) . . ?
F2 C17 S1 107.59(11) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C1 O1 N1 C18 -89.25(13) . . . . ?
C1 O1 N1 C3 26.63(13) . . . . ?
N1 O1 C1 C2 -14.30(15) . . . . ?
N1 O1 C1 C10 166.58(11) . . . . ?
O1 C1 C2 C3 -4.17(16) . . . . ?
C10 C1 C2 C3 174.72(15) . . . . ?
O1 C1 C2 S1 156.38(10) . . . . ?
C10 C1 C2 S1 -24.7(2) . . . . ?
O2 S1 C2 C1 -121.71(13) . . . . ?
C17 S1 C2 C1 131.63(13) . . . . ?
O2 S1 C2 C3 35.30(14) . . . . ?
C17 S1 C2 C3 -71.36(13) . . . . ?
C18 N1 C3 C4 -154.29(13) . . . . ?
O1 N1 C3 C4 94.63(13) . . . . ?
C18 N1 C3 C2 83.76(14) . . . . ?
O1 N1 C3 C2 -27.31(13) . . . . ?
C1 C2 C3 N1 20.47(15) . . . . ?
S1 C2 C3 N1 -139.41(11) . . . . ?
C1 C2 C3 C4 -98.72(14) . . . . ?
S1 C2 C3 C4 101.40(14) . . . . ?
N1 C3 C4 C5 -84.85(17) . . . . ?
C2 C3 C4 C5 29.4(2) . . . . ?
N1 C3 C4 C9 93.94(17) . . . . ?
C2 C3 C4 C9 -151.83(14) . . . . ?
C9 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 178.02(16) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C3 C4 C9 C8 -178.51(16) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C2 C1 C10 C11 -24.0(2) . . . . ?
O1 C1 C10 C11 154.84(14) . . . . ?
C2 C1 C10 C15 155.48(16) . . . . ?
O1 C1 C10 C15 -25.66(19) . . . . ?
C15 C10 C11 C12 -2.5(3) . . . . ?
C1 C10 C11 C12 177.01(16) . . . . ?
C10 C11 C12 C13 3.2(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C12 C13 C14 C16 178.75(18) . . . . ?
C13 C14 C15 C10 2.3(2) . . . . ?
C16 C14 C15 C10 -178.05(15) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C1 C10 C15 C14 -179.80(13) . . . . ?
O2 S1 C17 F1 -51.73(13) . . . . ?
C2 S1 C17 F1 59.09(13) . . . . ?
O2 S1 C17 F3 -174.79(12) . . . . ?
C2 S1 C17 F3 -63.97(13) . . . . ?
O2 S1 C17 F2 67.14(12) . . . . ?
C2 S1 C17 F2 177.96(11) . . . . ?

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
C3 H3 O2 0.99 2.57 3.3953(18) 140.8 2_667
C18 H18A O1 0.97 2.56 3.457(2) 153.5 2_666
C3 H3 O2 0.99 2.57 3.3953(18) 140.8 2_667
C18 H18A O1 0.97 2.56 3.457(2) 153.5 2_666

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v23144_0m
_database_code_depnum_ccdc_archive 'CCDC 2260516'
loop_
_audit_author_name
_audit_author_address
'Tianming Liao'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 F3 O2 S'
_chemical_formula_weight         324.31

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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   8.8998(2)
_cell_length_b                   16.2836(4)
_cell_length_c                   10.5436(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.4230(10)
_cell_angle_gamma                90
_cell_volume                     1457.88(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6827
_cell_measurement_theta_min      4.760
_cell_measurement_theta_max      54.948

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13887
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.705
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2840
_reflns_number_gt                2394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0192P)²+0.7644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2840
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.20219(5) 0.43960(3) 0.60032(4) 0.03339(12) Uani 1 1 d . . . . .
F1 F 0.37644(12) 0.43596(8) 0.43394(10) 0.0526(3) Uani 1 1 d . . . . .
F2 F 0.27609(17) 0.32036(7) 0.46052(12) 0.0665(4) Uani 1 1 d . . . . .
F3 F 0.13052(13) 0.41521(9) 0.34558(11) 0.0612(4) Uani 1 1 d . . . . .
O1 O 0.34719(15) 0.28880(8) 0.75721(14) 0.0497(4) Uani 1 1 d . . . . .
O2 O 0.17952(14) 0.52844(8) 0.57390(13) 0.0447(3) Uani 1 1 d . . . . .
C1 C 0.68601(19) 0.35573(10) 0.66907(16) 0.0324(4) Uani 1 1 d . . . . .
H1 H 0.6423 0.4038 0.6234 0.039 Uiso 1 1 calc R U . . .
C2 C 0.8323(2) 0.32917(11) 0.66625(17) 0.0374(4) Uani 1 1 d . . . . .
H2 H 0.8866 0.3584 0.6167 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8989(2) 0.25995(12) 0.73588(19) 0.0447(5) Uani 1 1 d . . . . .
H3 H 0.9996 0.2427 0.7355 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8176(2) 0.21587(12) 0.8062(2) 0.0475(5) Uani 1 1 d . . . . .
H4 H 0.8631 0.1687 0.8537 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6697(2) 0.24098(11) 0.80699(18) 0.0399(4) Uani 1 1 d . . . . .
H5 H 0.6138 0.2102 0.8534 0.048 Uiso 1 1 calc R U . . .
C6 C 0.60317(19) 0.31174(10) 0.73918(16) 0.0301(4) Uani 1 1 d . . . . .
C7 C 0.44363(19) 0.33753(10) 0.74102(16) 0.0323(4) Uani 1 1 d . . . . .
C8 C 0.39773(18) 0.42576(10) 0.71507(16) 0.0291(4) Uani 1 1 d . . . . .
C9 C 0.46637(19) 0.49455(10) 0.77300(16) 0.0307(4) Uani 1 1 d . . . . .
H9 H 0.4130 0.5431 0.7377 0.037 Uiso 1 1 calc R U . . .
C10 C 0.61145(19) 0.50689(10) 0.88272(16) 0.0311(4) Uani 1 1 d . . . . .
C11 C 0.6781(2) 0.58516(11) 0.89989(19) 0.0414(4) Uani 1 1 d . . . . .
H11 H 0.6300 0.6277 0.8415 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8144(2) 0.60086(13) 1.0021(2) 0.0485(5) Uani 1 1 d . . . . .
H12 H 0.8585 0.6538 1.0126 0.058 Uiso 1 1 calc R U . . .
C13 C 0.8855(2) 0.53924(14) 1.08828(19) 0.0483(5) Uani 1 1 d . . . . .
H13 H 0.9793 0.5497 1.1564 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8189(2) 0.46217(13) 1.07461(18) 0.0437(5) Uani 1 1 d . . . . .
H14 H 0.8667 0.4204 1.1347 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6828(2) 0.44576(11) 0.97354(16) 0.0361(4) Uani 1 1 d . . . . .
H15 H 0.6378 0.3931 0.9658 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2509(2) 0.39989(11) 0.45183(17) 0.0380(4) 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 O2 1.4757(13) . ?
S1 C8 1.8116(16) . ?
S1 C16 1.8613(18) . ?
F1 C16 1.325(2) . ?
F2 C16 1.313(2) . ?
F3 C16 1.322(2) . ?
O1 C7 1.218(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9400 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.486(2) . ?
C7 C8 1.496(2) . ?
C8 C9 1.333(2) . ?
C9 C10 1.467(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.395(2) . ?
C10 C15 1.395(2) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(2) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?

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
O2 S1 C8 107.32(7) . . ?
O2 S1 C16 103.59(8) . . ?
C8 S1 C16 95.70(7) . . ?
C2 C1 C6 120.27(16) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.17(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.97(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.18(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.14(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.24(16) . . ?
C1 C6 C7 121.50(14) . . ?
C5 C6 C7 119.24(15) . . ?
O1 C7 C6 122.26(16) . . ?
O1 C7 C8 119.07(15) . . ?
C6 C7 C8 118.59(14) . . ?
C9 C8 C7 131.33(15) . . ?
C9 C8 S1 114.72(12) . . ?
C7 C8 S1 113.37(11) . . ?
C8 C9 C10 130.61(16) . . ?
C8 C9 H9 114.7 . . ?
C10 C9 H9 114.7 . . ?
C11 C10 C15 118.32(16) . . ?
C11 C10 C9 117.87(16) . . ?
C15 C10 C9 123.76(15) . . ?
C12 C11 C10 120.63(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.17(19) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.87(18) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.56(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.40(17) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
F2 C16 F3 108.87(15) . . ?
F2 C16 F1 108.30(16) . . ?
F3 C16 F1 107.45(15) . . ?
F2 C16 S1 111.21(13) . . ?
F3 C16 S1 108.26(12) . . ?
F1 C16 S1 112.62(12) . . ?

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
C6 C1 C2 C3 -1.7(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 -178.31(15) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 179.84(16) . . . . ?
C1 C6 C7 O1 152.63(17) . . . . ?
C5 C6 C7 O1 -26.0(2) . . . . ?
C1 C6 C7 C8 -24.2(2) . . . . ?
C5 C6 C7 C8 157.19(15) . . . . ?
O1 C7 C8 C9 128.4(2) . . . . ?
C6 C7 C8 C9 -54.7(2) . . . . ?
O1 C7 C8 S1 -42.2(2) . . . . ?
C6 C7 C8 S1 134.70(13) . . . . ?
O2 S1 C8 C9 13.36(15) . . . . ?
C16 S1 C8 C9 119.53(13) . . . . ?
O2 S1 C8 C7 -174.39(11) . . . . ?
C16 S1 C8 C7 -68.23(13) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
S1 C8 C9 C10 170.52(14) . . . . ?
C8 C9 C10 C11 163.00(17) . . . . ?
C8 C9 C10 C15 -19.5(3) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
C9 C10 C11 C12 179.58(16) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C11 C10 C15 C14 -2.3(2) . . . . ?
C9 C10 C15 C14 -179.69(16) . . . . ?
O2 S1 C16 F2 179.54(12) . . . . ?
C8 S1 C16 F2 70.15(13) . . . . ?
O2 S1 C16 F3 -60.89(13) . . . . ?
C8 S1 C16 F3 -170.28(12) . . . . ?
O2 S1 C16 F1 57.77(14) . . . . ?
C8 S1 C16 F1 -51.62(14) . . . . ?

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
C9 H9 O2 0.94 2.28 2.832(2) 116.7 .

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

