# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_atk_dk_ac_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2513822'
loop_
_audit_author_name
_audit_author_address
'DEVENDRA KUMAR'
;IIT Guwahati
India
;
_audit_update_record             
;
2025-12-06 deposited with the CCDC.	2026-04-01 downloaded from the CCDC.
;
_audit_creation_date             2025-12-05
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Cl O3 S2'
_chemical_formula_sum            'C15 H11 Cl O3 S2'
_chemical_formula_weight         338.81
_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'
Cl Cl 0.1484 0.1585 '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      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                   17.1285(14)
_cell_length_b                   4.0509(3)
_cell_length_c                   22.3190(18)
_cell_angle_alpha                90
_cell_angle_beta                 106.564(2)
_cell_angle_gamma                90
_cell_volume                     1484.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1653 before and 0.0861 after correction.
The Ratio of minimum to maximum transmission is 0.8093.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.8978
_exptl_crystal_size_mid          0.4633
_exptl_crystal_size_min          0.2132
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29013
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.904
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2334
_reflns_number_total             2598
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+1.7469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_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
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00C), C00G(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00F(H00F), C00H(H00H), C00J(H00J)
2.c Idealised Me refined as rotating group:
 C00L(H00G,H00I,H00K)
;
_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
S2 S 0.43143(4) 0.32966(17) 0.69647(3) 0.03317(18) Uani 1 1 d . . . . .
S002 S 0.59681(3) 0.34574(16) 0.67660(3) 0.03159(18) Uani 1 1 d . . . . .
Cl03 Cl 0.08534(4) 0.7841(3) 0.54116(5) 0.0813(3) Uani 1 1 d . . . . .
O004 O 0.37904(10) 0.9098(5) 0.51970(8) 0.0460(5) Uani 1 1 d . . . . .
O005 O 0.83238(10) 0.7366(6) 0.64074(9) 0.0503(5) Uani 1 1 d . . . . .
C006 C 0.47458(13) 0.6132(6) 0.59688(10) 0.0271(5) Uani 1 1 d . . . . .
C007 C 0.49476(13) 0.4421(6) 0.65236(10) 0.0273(5) Uani 1 1 d . . . . .
O008 O 0.88580(14) 0.9910(8) 0.73110(12) 0.0829(8) Uani 1 1 d . . . . .
C009 C 0.32607(14) 0.6435(6) 0.59323(11) 0.0305(5) Uani 1 1 d . . . . .
C00A C 0.39276(14) 0.7356(6) 0.56630(10) 0.0303(5) Uani 1 1 d . . . . .
C00B C 0.54339(14) 0.6643(6) 0.57432(11) 0.0311(5) Uani 1 1 d . . . . .
H00B H 0.540437 0.776556 0.537399 0.037 Uiso 1 1 calc R U . . .
C00C C 0.61289(14) 0.5364(6) 0.61093(11) 0.0299(5) Uani 1 1 d . . . . .
C00D C 0.33766(14) 0.4739(6) 0.64983(11) 0.0314(6) Uani 1 1 d . . . . .
C00E C 0.69641(14) 0.5480(7) 0.60199(11) 0.0347(6) Uani 1 1 d . . . . .
H00A H 0.695079 0.686343 0.566233 0.042 Uiso 1 1 calc R U . . .
H00C H 0.712063 0.327357 0.593081 0.042 Uiso 1 1 calc R U . . .
C00F C 0.24702(15) 0.7374(7) 0.56042(12) 0.0396(6) Uani 1 1 d . . . . .
H00F H 0.237843 0.848469 0.522578 0.048 Uiso 1 1 calc R U . . .
C00G C 0.75931(14) 0.6809(7) 0.65869(12) 0.0385(6) Uani 1 1 d . . . . .
H00D H 0.740501 0.885686 0.672347 0.046 Uiso 1 1 calc R U . . .
H00E H 0.769392 0.523108 0.692729 0.046 Uiso 1 1 calc R U . . .
C00H C 0.27135(15) 0.4101(8) 0.67270(13) 0.0431(7) Uani 1 1 d . . . . .
H00H H 0.279569 0.300758 0.710633 0.052 Uiso 1 1 calc R U . . .
C00I C 0.18300(15) 0.6675(8) 0.58343(14) 0.0484(7) Uani 1 1 d . . . . .
C00J C 0.19440(16) 0.5063(9) 0.64003(14) 0.0516(8) Uani 1 1 d . . . . .
H00J H 0.150460 0.464139 0.655579 0.062 Uiso 1 1 calc R U . . .
C00K C 0.89203(17) 0.9015(9) 0.68199(16) 0.0554(8) Uani 1 1 d . . . . .
C00L C 0.96383(19) 0.9522(12) 0.6579(2) 0.0830(12) Uani 1 1 d . . . . .
H00G H 0.947272 1.070623 0.619026 0.124 Uiso 1 1 calc R U . . .
H00I H 0.985847 0.741841 0.651287 0.124 Uiso 1 1 calc R U . . .
H00K H 1.004597 1.076863 0.687730 0.124 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
S2 C007 1.721(2) . ?
S2 C00D 1.747(2) . ?
S002 C007 1.721(2) . ?
S002 C00C 1.747(2) . ?
Cl03 C00I 1.735(3) . ?
O004 C00A 1.223(3) . ?
O005 C00G 1.437(3) . ?
O005 C00K 1.342(4) . ?
C006 C007 1.375(3) . ?
C006 C00A 1.460(3) . ?
C006 C00B 1.423(3) . ?
O008 C00K 1.188(4) . ?
C009 C00A 1.482(3) . ?
C009 C00D 1.402(3) . ?
C009 C00F 1.396(3) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.341(3) . ?
C00C C00E 1.501(3) . ?
C00D C00H 1.396(3) . ?
C00E H00A 0.9700 . ?
C00E H00C 0.9700 . ?
C00E C00G 1.508(4) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.366(4) . ?
C00G H00D 0.9700 . ?
C00G H00E 0.9700 . ?
C00H H00H 0.9300 . ?
C00H C00J 1.368(4) . ?
C00I C00J 1.386(4) . ?
C00J H00J 0.9300 . ?
C00K C00L 1.491(4) . ?
C00L H00G 0.9600 . ?
C00L H00I 0.9600 . ?
C00L H00K 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
C007 S2 C00D 101.13(11) . . ?
C007 S002 C00C 91.43(11) . . ?
C00K O005 C00G 116.1(2) . . ?
C007 C006 C00A 123.6(2) . . ?
C007 C006 C00B 111.8(2) . . ?
C00B C006 C00A 124.5(2) . . ?
S002 C007 S2 120.63(14) . . ?
C006 C007 S2 127.67(18) . . ?
C006 C007 S002 111.69(17) . . ?
C00D C009 C00A 124.2(2) . . ?
C00F C009 C00A 117.6(2) . . ?
C00F C009 C00D 118.2(2) . . ?
O004 C00A C006 121.3(2) . . ?
O004 C00A C009 120.4(2) . . ?
C006 C00A C009 118.2(2) . . ?
C006 C00B H00B 122.9 . . ?
C00C C00B C006 114.2(2) . . ?
C00C C00B H00B 122.9 . . ?
C00B C00C S002 110.93(18) . . ?
C00B C00C C00E 128.4(2) . . ?
C00E C00C S002 120.66(18) . . ?
C009 C00D S2 124.82(18) . . ?
C00H C00D S2 115.21(19) . . ?
C00H C00D C009 120.0(2) . . ?
C00C C00E H00A 109.1 . . ?
C00C C00E H00C 109.1 . . ?
C00C C00E C00G 112.3(2) . . ?
H00A C00E H00C 107.9 . . ?
C00G C00E H00A 109.1 . . ?
C00G C00E H00C 109.1 . . ?
C009 C00F H00F 119.7 . . ?
C00I C00F C009 120.6(3) . . ?
C00I C00F H00F 119.7 . . ?
O005 C00G C00E 107.0(2) . . ?
O005 C00G H00D 110.3 . . ?
O005 C00G H00E 110.3 . . ?
C00E C00G H00D 110.3 . . ?
C00E C00G H00E 110.3 . . ?
H00D C00G H00E 108.6 . . ?
C00D C00H H00H 119.6 . . ?
C00J C00H C00D 120.9(3) . . ?
C00J C00H H00H 119.6 . . ?
C00F C00I Cl03 119.5(2) . . ?
C00F C00I C00J 121.4(2) . . ?
C00J C00I Cl03 119.2(2) . . ?
C00H C00J C00I 118.9(3) . . ?
C00H C00J H00J 120.5 . . ?
C00I C00J H00J 120.5 . . ?
O005 C00K C00L 111.5(3) . . ?
O008 C00K O005 122.3(3) . . ?
O008 C00K C00L 126.3(3) . . ?
C00K C00L H00G 109.5 . . ?
C00K C00L H00I 109.5 . . ?
C00K C00L H00K 109.5 . . ?
H00G C00L H00I 109.5 . . ?
H00G C00L H00K 109.5 . . ?
H00I C00L H00K 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
S2 C00D C00H C00J -179.0(2) . . . . ?
S002 C00C C00E C00G -51.6(3) . . . . ?
Cl03 C00I C00J C00H 179.0(3) . . . . ?
C006 C00B C00C S002 -0.5(3) . . . . ?
C006 C00B C00C C00E -179.1(2) . . . . ?
C007 S2 C00D C009 -1.9(3) . . . . ?
C007 S2 C00D C00H 178.2(2) . . . . ?
C007 S002 C00C C00B 0.4(2) . . . . ?
C007 S002 C00C C00E 179.2(2) . . . . ?
C007 C006 C00A O004 173.9(2) . . . . ?
C007 C006 C00A C009 -6.0(4) . . . . ?
C007 C006 C00B C00C 0.2(3) . . . . ?
C009 C00D C00H C00J 1.1(4) . . . . ?
C009 C00F C00I Cl03 -179.4(2) . . . . ?
C009 C00F C00I C00J 0.9(5) . . . . ?
C00A C006 C007 S2 1.2(4) . . . . ?
C00A C006 C007 S002 -178.07(19) . . . . ?
C00A C006 C00B C00C 178.4(2) . . . . ?
C00A C009 C00D S2 -2.5(4) . . . . ?
C00A C009 C00D C00H 177.3(2) . . . . ?
C00A C009 C00F C00I -178.4(3) . . . . ?
C00B C006 C007 S2 179.33(18) . . . . ?
C00B C006 C007 S002 0.1(3) . . . . ?
C00B C006 C00A O004 -4.0(4) . . . . ?
C00B C006 C00A C009 176.0(2) . . . . ?
C00B C00C C00E C00G 126.9(3) . . . . ?
C00C S002 C007 S2 -179.59(16) . . . . ?
C00C S002 C007 C006 -0.31(19) . . . . ?
C00C C00E C00G O005 -169.7(2) . . . . ?
C00D S2 C007 S002 -178.22(15) . . . . ?
C00D S2 C007 C006 2.6(3) . . . . ?
C00D C009 C00A O004 -173.2(2) . . . . ?
C00D C009 C00A C006 6.8(4) . . . . ?
C00D C009 C00F C00I 0.5(4) . . . . ?
C00D C00H C00J C00I 0.3(5) . . . . ?
C00F C009 C00A O004 5.6(4) . . . . ?
C00F C009 C00A C006 -174.4(2) . . . . ?
C00F C009 C00D S2 178.6(2) . . . . ?
C00F C009 C00D C00H -1.5(4) . . . . ?
C00F C00I C00J C00H -1.3(5) . . . . ?
C00G O005 C00K O008 1.5(5) . . . . ?
C00G O005 C00K C00L -178.6(3) . . . . ?
C00K O005 C00G C00E 170.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_atk25062_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2518535'
loop_
_audit_author_name
_audit_author_address
'DEVENDRA KUMAR'
;IIT Guwahati
India
;
_audit_update_record             
;
2025-12-24 deposited with the CCDC.	2026-04-01 downloaded from the CCDC.
;
_audit_creation_date             2025-12-23
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F O3 S2'
_chemical_formula_sum            'C16 H13 F O3 S2'
_chemical_formula_weight         336.38
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4957(4)
_cell_length_b                   7.5172(4)
_cell_length_c                   13.7183(7)
_cell_angle_alpha                91.097(2)
_cell_angle_beta                 90.8560(10)
_cell_angle_gamma                101.684(2)
_cell_volume                     756.69(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5862
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1678 before and 0.0844 after correction.
The Ratio of minimum to maximum transmission is 0.7865.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.8456
_exptl_crystal_size_mid          0.4225
_exptl_crystal_size_min          0.2012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17631
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.029
_diffrn_reflns_theta_min         2.768
_diffrn_ambient_temperature      299.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2550
_reflns_number_total             2971
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.069
_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)+(0.0356P)²+0.3745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_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
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C10(H10)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 0.73108(7) 0.74945(7) 0.43831(4) 0.04382(16) Uani 1 1 d . . . . .
S2 S 0.48734(7) 0.58682(7) 0.27150(4) 0.04346(16) Uani 1 1 d . . . . .
F1 F 0.9489(2) 1.0459(2) 0.75751(11) 0.0736(4) Uani 1 1 d . . . . .
O2 O 0.18320(19) 0.7333(2) 0.56596(10) 0.0515(4) Uani 1 1 d . . . . .
O3 O -0.1763(2) 0.1863(2) 0.11544(11) 0.0629(5) Uani 1 1 d . . . . .
O4 O -0.3037(3) 0.1618(3) -0.03142(14) 0.0971(7) Uani 1 1 d . . . . .
C1 C 0.5020(3) 0.8205(2) 0.58670(13) 0.0348(4) Uani 1 1 d . . . . .
C2 C 0.6793(3) 0.8274(2) 0.55292(14) 0.0367(4) Uani 1 1 d . . . . .
C3 C 0.8307(3) 0.9022(3) 0.61188(16) 0.0462(5) Uani 1 1 d . . . . .
H3 H 0.948407 0.905000 0.590498 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8014(3) 0.9709(3) 0.70129(16) 0.0493(5) Uani 1 1 d . . . . .
C5 C 0.6308(3) 0.9684(3) 0.73802(15) 0.0484(5) Uani 1 1 d . . . . .
H5 H 0.616413 1.016279 0.799764 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4829(3) 0.8930(3) 0.68022(14) 0.0421(5) Uani 1 1 d . . . . .
H6 H 0.366513 0.889632 0.703635 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3342(3) 0.7398(2) 0.53072(14) 0.0357(4) Uani 1 1 d . . . . .
C8 C 0.3516(2) 0.6695(2) 0.43288(13) 0.0339(4) Uani 1 1 d . . . . .
C9 C 0.5166(3) 0.6720(2) 0.38907(14) 0.0358(4) Uani 1 1 d . . . . .
C10 C 0.2015(3) 0.5937(3) 0.36957(14) 0.0385(4) Uani 1 1 d . . . . .
H10 H 0.080694 0.579962 0.387972 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2510(3) 0.5438(3) 0.28055(14) 0.0395(4) Uani 1 1 d . . . . .
C12 C 0.1370(3) 0.4617(3) 0.19413(15) 0.0492(5) Uani 1 1 d . . . . .
H12A H 0.152431 0.337724 0.184027 0.059 Uiso 1 1 calc R U . . .
H12B H 0.180299 0.529143 0.136617 0.059 Uiso 1 1 calc R U . . .
C13 C -0.0642(3) 0.4612(3) 0.20527(16) 0.0542(6) Uani 1 1 d . . . . .
H13A H -0.107450 0.394250 0.262929 0.065 Uiso 1 1 calc R U . . .
H13B H -0.079770 0.585251 0.215026 0.065 Uiso 1 1 calc R U . . .
C14 C -0.1787(3) 0.3776(3) 0.11825(17) 0.0594(6) Uani 1 1 d . . . . .
H14A H -0.302607 0.395564 0.124364 0.071 Uiso 1 1 calc R U . . .
H14B H -0.129004 0.433681 0.058774 0.071 Uiso 1 1 calc R U . . .
C15 C -0.2443(3) 0.0928(4) 0.03629(18) 0.0624(7) Uani 1 1 d . . . . .
C16 C -0.2391(5) -0.1042(4) 0.0426(3) 0.0909(10) Uani 1 1 d . . . . .
H16A H -0.258268 -0.160152 -0.021178 0.136 Uiso 1 1 calc R U . . .
H16B H -0.333118 -0.162157 0.084979 0.136 Uiso 1 1 calc R U . . .
H16C H -0.122498 -0.116900 0.068182 0.136 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 C2 1.744(2) . ?
S1 C9 1.719(2) . ?
S2 C9 1.7183(19) . ?
S2 C11 1.742(2) . ?
F1 C4 1.356(2) . ?
O2 C7 1.230(2) . ?
O3 C14 1.441(3) . ?
O3 C15 1.320(3) . ?
O4 C15 1.196(3) . ?
C1 C2 1.405(3) . ?
C1 C6 1.405(3) . ?
C1 C7 1.478(3) . ?
C2 C3 1.398(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(3) . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.450(3) . ?
C8 C9 1.380(3) . ?
C8 C10 1.427(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.350(3) . ?
C11 C12 1.498(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.517(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.510(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.494(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C9 S1 C2 101.07(9) . . ?
C9 S2 C11 91.92(9) . . ?
C15 O3 C14 117.1(2) . . ?
C2 C1 C7 124.24(16) . . ?
C6 C1 C2 117.92(18) . . ?
C6 C1 C7 117.83(17) . . ?
C1 C2 S1 124.77(15) . . ?
C3 C2 S1 114.79(15) . . ?
C3 C2 C1 120.44(18) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 H3 120.9 . . ?
F1 C4 C3 118.0(2) . . ?
F1 C4 C5 118.2(2) . . ?
C3 C4 C5 123.8(2) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.59(19) . . ?
C6 C5 H5 121.2 . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 122.0(2) . . ?
C5 C6 H6 119.0 . . ?
O2 C7 C1 120.85(17) . . ?
O2 C7 C8 120.67(17) . . ?
C8 C7 C1 118.48(16) . . ?
C9 C8 C7 123.68(17) . . ?
C9 C8 C10 111.85(16) . . ?
C10 C8 C7 124.45(16) . . ?
S2 C9 S1 120.82(11) . . ?
C8 C9 S1 127.68(15) . . ?
C8 C9 S2 111.49(14) . . ?
C8 C10 H10 123.1 . . ?
C11 C10 C8 113.88(17) . . ?
C11 C10 H10 123.1 . . ?
C10 C11 S2 110.85(15) . . ?
C10 C11 C12 130.47(19) . . ?
C12 C11 S2 118.68(15) . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C11 C12 C13 113.25(17) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C12 113.09(19) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
O3 C14 C13 107.48(19) . . ?
O3 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C13 C14 H14A 110.2 . . ?
C13 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
O3 C15 C16 112.4(2) . . ?
O4 C15 O3 122.4(3) . . ?
O4 C15 C16 125.2(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
S1 C2 C3 C4 178.12(16) . . . . ?
S2 C11 C12 C13 -170.12(16) . . . . ?
F1 C4 C5 C6 179.71(18) . . . . ?
O2 C7 C8 C9 -179.79(18) . . . . ?
O2 C7 C8 C10 1.8(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C1 C7 C8 C9 0.6(3) . . . . ?
C1 C7 C8 C10 -177.82(17) . . . . ?
C2 S1 C9 S2 177.28(11) . . . . ?
C2 S1 C9 C8 -2.0(2) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C7 O2 177.72(18) . . . . ?
C2 C1 C7 C8 -2.7(3) . . . . ?
C2 C3 C4 F1 -178.97(18) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 C1 C2 S1 -178.53(14) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C1 C7 O2 -1.5(3) . . . . ?
C6 C1 C7 C8 178.12(17) . . . . ?
C7 C1 C2 S1 2.3(3) . . . . ?
C7 C1 C2 C3 -178.33(18) . . . . ?
C7 C1 C6 C5 179.14(18) . . . . ?
C7 C8 C9 S1 1.8(3) . . . . ?
C7 C8 C9 S2 -177.47(14) . . . . ?
C7 C8 C10 C11 177.48(17) . . . . ?
C8 C10 C11 S2 0.6(2) . . . . ?
C8 C10 C11 C12 -179.4(2) . . . . ?
C9 S1 C2 C1 -0.05(18) . . . . ?
C9 S1 C2 C3 -179.47(15) . . . . ?
C9 S2 C11 C10 0.07(16) . . . . ?
C9 S2 C11 C12 -179.92(17) . . . . ?
C9 C8 C10 C11 -1.1(2) . . . . ?
C10 C8 C9 S1 -179.54(14) . . . . ?
C10 C8 C9 S2 1.1(2) . . . . ?
C10 C11 C12 C13 9.9(3) . . . . ?
C11 S2 C9 S1 179.92(12) . . . . ?
C11 S2 C9 C8 -0.71(15) . . . . ?
C11 C12 C13 C14 -179.7(2) . . . . ?
C12 C13 C14 O3 68.0(3) . . . . ?
C14 O3 C15 O4 1.0(4) . . . . ?
C14 O3 C15 C16 -178.5(2) . . . . ?
C15 O3 C14 C13 -169.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
