# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_zh_0m
_database_code_depnum_ccdc_archive 'CCDC 2118496'
loop_
_audit_author_name
_audit_author_address
'Chuanle Zhu'
;South China University of Technology
China
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 F2 O S'
_chemical_formula_sum            'C24 H18 F2 O S'
_chemical_formula_weight         392.44
_chemical_absolute_configuration rmad
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7949(4)
_cell_length_b                   15.4144(12)
_cell_length_c                   21.1109(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1885.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3685
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.677
_cell_measurement_theta_min      2.338
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1158 before and 0.0684 after correction. The Ratio of minimum to maximum transmission is 0.8838. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14420
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_min         1.929
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3064
_reflns_number_total             3865
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.095
_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)+(0.0507P)²+0.5370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C18(H18), C3(H3), C2(H2), C23(H23), C24(H24), C16(H16), C21(H21),
 C8(H8), C19(H19), C5(H5), C7(H7), C20(H20), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5541(2) 0.54642(8) 0.47352(5) 0.0336(3) Uani 1 1 d . . . . .
F1 F 0.9381(4) 0.53640(16) 0.40752(11) 0.0316(6) Uani 1 1 d . . . . .
F2 F 0.6441(4) 0.47235(17) 0.36508(10) 0.0317(6) Uani 1 1 d . . . . .
O1 O 0.6392(5) 0.3626(2) 0.48515(13) 0.0299(7) Uani 1 1 d . . . . .
C11 C 0.8296(7) 0.4020(3) 0.45153(19) 0.0264(10) Uani 1 1 d . . . . .
C1 C 0.9360(8) 0.3432(3) 0.40168(18) 0.0248(9) Uani 1 1 d . . . . .
C17 C 0.4081(7) 0.7613(3) 0.36911(19) 0.0268(10) Uani 1 1 d . . . . .
C9 C 0.9206(8) 0.2154(3) 0.33519(19) 0.0274(10) Uani 1 1 d . . . . .
C10 C 0.8231(8) 0.2698(3) 0.38248(18) 0.0268(10) Uani 1 1 d . . . . .
H10 H 0.678627 0.255159 0.400872 0.032 Uiso 1 1 calc R . . . .
C22 C 0.5944(8) 0.8175(3) 0.38387(18) 0.0275(10) Uani 1 1 d . . . . .
C14 C 0.7496(8) 0.4879(3) 0.42230(18) 0.0247(9) Uani 1 1 d . . . . .
C4 C 1.1359(8) 0.2389(3) 0.30768(19) 0.0307(11) Uani 1 1 d . . . . .
C15 C 0.5724(8) 0.6507(3) 0.43694(18) 0.0288(10) Uani 1 1 d . . . . .
C18 C 0.2373(9) 0.7907(3) 0.3265(2) 0.0338(11) Uani 1 1 d . . . . .
H18 H 0.112842 0.753396 0.315840 0.041 Uiso 1 1 calc R . . . .
C3 C 1.2449(9) 0.3153(3) 0.32823(19) 0.0324(11) Uani 1 1 d . . . . .
H3 H 1.387721 0.331857 0.309735 0.039 Uiso 1 1 calc R . . . .
C2 C 1.1495(8) 0.3663(3) 0.37428(19) 0.0304(10) Uani 1 1 d . . . . .
H2 H 1.227055 0.417275 0.387872 0.036 Uiso 1 1 calc R . . . .
C23 C 0.7678(8) 0.7874(3) 0.42625(19) 0.0320(11) Uani 1 1 d . . . . .
H23 H 0.892951 0.824525 0.436614 0.038 Uiso 1 1 calc R . . . .
C24 C 0.7587(8) 0.7067(3) 0.45229(19) 0.0302(10) Uani 1 1 d . . . . .
H24 H 0.876240 0.688011 0.480541 0.036 Uiso 1 1 calc R . . . .
C16 C 0.4019(8) 0.6777(3) 0.39639(19) 0.0304(11) Uani 1 1 d . . . . .
H16 H 0.278028 0.639637 0.386540 0.036 Uiso 1 1 calc R . . . .
C12 C 0.9722(9) 0.4119(3) 0.51333(19) 0.0354(11) Uani 1 1 d . . . . .
H12A H 1.121120 0.380449 0.513276 0.042 Uiso 1 1 calc R . . . .
H12B H 0.990686 0.472509 0.528060 0.042 Uiso 1 1 calc R . . . .
C21 C 0.6011(9) 0.9010(3) 0.3567(2) 0.0363(12) Uani 1 1 d . . . . .
H21 H 0.723804 0.939473 0.366859 0.044 Uiso 1 1 calc R . . . .
C8 C 0.8112(9) 0.1379(3) 0.3151(2) 0.0362(11) Uani 1 1 d . . . . .
H8 H 0.667627 0.121668 0.333277 0.043 Uiso 1 1 calc R . . . .
C19 C 0.2468(9) 0.8715(3) 0.3005(2) 0.0398(12) Uani 1 1 d . . . . .
H19 H 0.129675 0.890384 0.272173 0.048 Uiso 1 1 calc R . . . .
C5 C 1.2319(9) 0.1832(3) 0.26102(19) 0.0358(12) Uani 1 1 d . . . . .
H5 H 1.375567 0.197906 0.242181 0.043 Uiso 1 1 calc R . . . .
C7 C 0.9097(10) 0.0860(3) 0.2696(2) 0.0409(13) Uani 1 1 d . . . . .
H7 H 0.834389 0.034340 0.256384 0.049 Uiso 1 1 calc R . . . .
C20 C 0.4318(10) 0.9268(3) 0.3160(2) 0.0430(12) Uani 1 1 d . . . . .
H20 H 0.438918 0.983045 0.297682 0.052 Uiso 1 1 calc R . . . .
C6 C 1.1230(9) 0.1097(4) 0.2428(2) 0.0422(13) Uani 1 1 d . . . . .
H6 H 1.191298 0.073597 0.211536 0.051 Uiso 1 1 calc R . . . .
C13 C 0.7738(9) 0.3629(4) 0.5443(2) 0.0459(14) Uani 1 1 d . . . . .
H13A H 0.817402 0.304034 0.558817 0.055 Uiso 1 1 calc R . . . .
H13B H 0.698743 0.395703 0.578952 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C14 1.807(4) . ?
S1 C15 1.786(5) . ?
F1 C14 1.360(5) . ?
F2 C14 1.375(5) . ?
O1 C11 1.445(5) . ?
O1 C13 1.473(5) . ?
C11 C1 1.520(6) . ?
C11 C14 1.533(6) . ?
C11 C12 1.552(6) . ?
C1 C10 1.368(6) . ?
C1 C2 1.412(6) . ?
C17 C22 1.419(6) . ?
C17 C18 1.412(6) . ?
C17 C16 1.411(6) . ?
C9 C10 1.421(6) . ?
C9 C4 1.423(6) . ?
C9 C8 1.417(6) . ?
C10 H10 0.9500 . ?
C22 C23 1.423(6) . ?
C22 C21 1.411(7) . ?
C4 C3 1.405(7) . ?
C4 C5 1.420(6) . ?
C15 C24 1.420(6) . ?
C15 C16 1.372(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.362(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.367(6) . ?
C2 H2 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.360(7) . ?
C24 H24 0.9500 . ?
C16 H16 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.524(7) . ?
C21 H21 0.9500 . ?
C21 C20 1.364(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.374(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.408(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.353(7) . ?
C7 H7 0.9500 . ?
C7 C6 1.407(7) . ?
C20 H20 0.9500 . ?
C6 H6 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C15 S1 C14 98.81(19) . . ?
C11 O1 C13 90.6(3) . . ?
O1 C11 C1 113.5(4) . . ?
O1 C11 C14 109.2(3) . . ?
O1 C11 C12 92.0(3) . . ?
C1 C11 C14 111.1(3) . . ?
C1 C11 C12 115.2(4) . . ?
C14 C11 C12 114.5(4) . . ?
C10 C1 C11 120.3(4) . . ?
C10 C1 C2 120.4(4) . . ?
C2 C1 C11 119.3(4) . . ?
C18 C17 C22 118.5(4) . . ?
C16 C17 C22 119.2(4) . . ?
C16 C17 C18 122.4(4) . . ?
C10 C9 C4 119.0(4) . . ?
C8 C9 C10 122.0(4) . . ?
C8 C9 C4 119.0(4) . . ?
C1 C10 C9 120.4(4) . . ?
C1 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C17 C22 C23 118.4(4) . . ?
C21 C22 C17 119.3(4) . . ?
C21 C22 C23 122.3(4) . . ?
F1 C14 S1 111.5(3) . . ?
F1 C14 F2 104.6(3) . . ?
F1 C14 C11 108.9(4) . . ?
F2 C14 S1 109.5(3) . . ?
F2 C14 C11 109.7(3) . . ?
C11 C14 S1 112.3(3) . . ?
C3 C4 C9 118.8(4) . . ?
C3 C4 C5 123.0(4) . . ?
C5 C4 C9 118.2(5) . . ?
C24 C15 S1 119.6(3) . . ?
C16 C15 S1 120.0(4) . . ?
C16 C15 C24 120.4(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.5(5) . . ?
C19 C18 H18 119.2 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H3 119.3 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 120.0 . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.7(4) . . ?
C24 C23 H23 119.2 . . ?
C15 C24 H24 120.2 . . ?
C23 C24 C15 119.5(4) . . ?
C23 C24 H24 120.2 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 H16 119.6 . . ?
C11 C12 H12A 114.5 . . ?
C11 C12 H12B 114.5 . . ?
H12A C12 H12B 111.6 . . ?
C13 C12 C11 84.8(3) . . ?
C13 C12 H12A 114.5 . . ?
C13 C12 H12B 114.5 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.2(5) . . ?
C20 C21 H21 119.9 . . ?
C9 C8 H8 119.5 . . ?
C7 C8 C9 120.9(5) . . ?
C7 C8 H8 119.5 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(5) . . ?
C20 C19 H19 120.3 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C8 C7 H7 120.2 . . ?
C8 C7 C6 119.6(5) . . ?
C6 C7 H7 120.2 . . ?
C21 C20 C19 121.2(5) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C5 C6 C7 120.9(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
O1 C13 C12 92.1(3) . . ?
O1 C13 H13A 113.3 . . ?
O1 C13 H13B 113.3 . . ?
C12 C13 H13A 113.3 . . ?
C12 C13 H13B 113.3 . . ?
H13A C13 H13B 110.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
