# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_emam-51
_database_code_depnum_ccdc_archive 'CCDC 2302018'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Faculty of Pharmacy, Mansoura University
Egypt
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;

_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Cl F3 N3 O S'
_chemical_formula_sum            'C16 H11 Cl F3 N3 O S'
_chemical_formula_weight         385.79
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   4.7906(2)
_cell_length_b                   13.1169(6)
_cell_length_c                   25.4767(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1600.90(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4484
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      75.9680
_cell_measurement_theta_min      3.4900
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.432
_exptl_absorpt_coefficient_mu    3.741
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0117
0 0 -1 0.0047
0 -1 1 0.0010
0 1 -1 0.0155
1 -1 -5 0.0899
-1 0 1 0.1294
3 1 -2 0.1388

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02

_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.399
_diffrn_reflns_theta_min         3.470
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  37.90   0.70   10.00    --  -38.50  19.00 -30.00  157
  2  ω     27.00  97.00   0.70   10.00    --   43.36-125.00 -90.00  100
  3  ω     27.00  97.00   0.70   10.00    --   43.36-125.00 120.00  100
  4  ω    103.00 176.50   0.70   40.00    --  111.00  77.00 120.00  105
  5  ω     71.00 176.70   0.70   40.00    --  111.00  15.00-180.00  151
  6  ω     38.00 108.00   0.70   40.00    --  111.00-111.00-150.00  100
  7  ω    103.00 176.50   0.70   40.00    --  111.00  77.00  90.00  105
  8  ω    103.00 176.50   0.70   40.00    --  111.00  77.00   0.00  105
  9  ω    103.00 176.50   0.70   40.00    --  111.00  77.00-180.00  105
 10  ω    103.00 176.50   0.70   40.00    --  111.00  77.00 150.00  105
 11  ω     40.00 139.40   0.70   40.00    --  111.00 -77.00 150.00  142
 12  ω     38.00 108.00   0.70   40.00    --  111.00-111.00-120.00  100
 13  ω     40.00 139.40   0.70   40.00    --  111.00 -77.00   0.00  142
 14  ω     18.00 110.40   0.70   10.00    --   43.36  57.00  30.00  132
 15  ω     18.00 110.40   0.70   10.00    --   43.36  57.00 -60.00  132
 16  ω     18.00 110.40   0.70   10.00    --   43.36  57.00-180.00  132
 17  ω     89.00 176.50   0.70   40.00    --  111.00  45.00-120.00  125
 18  ω     85.00 176.70   0.70   40.00    --  111.00  61.00  60.00  131
 19  ω     90.00 176.80   0.70   40.00    --  111.00  30.00 -60.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1859274000
_diffrn_orient_matrix_UB_12      -0.0560956000
_diffrn_orient_matrix_UB_13      0.0401005000
_diffrn_orient_matrix_UB_21      0.2097463000
_diffrn_orient_matrix_UB_22      0.0257213000
_diffrn_orient_matrix_UB_23      0.0438694000
_diffrn_orient_matrix_UB_31      -0.1581054000
_diffrn_orient_matrix_UB_32      0.0999747000
_diffrn_orient_matrix_UB_33      0.0111605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2874
_reflns_number_total             3244

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.035
_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)+(0.0545P)²+0.2988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1042
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C -0.0478(8) 0.3478(3) 0.58485(16) 0.0320(8) Uani 1 1 d . . . . .
C2 C 0.0264(8) 0.2743(3) 0.62184(18) 0.0343(8) Uani 1 1 d . . . . .
H2 H -0.057911 0.208810 0.621243 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2265(9) 0.2983(3) 0.65979(16) 0.0343(8) Uani 1 1 d . . . . .
H3 H 0.280278 0.248774 0.685039 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3458(8) 0.3941(3) 0.66056(15) 0.0300(8) Uani 1 1 d . . . . .
C5 C 0.2664(9) 0.4678(3) 0.62390(17) 0.0343(8) Uani 1 1 d . . . . .
H5 H 0.348256 0.533757 0.624904 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0676(9) 0.4447(3) 0.58595(16) 0.0351(9) Uani 1 1 d . . . . .
H6 H 0.011556 0.494717 0.561104 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5591(8) 0.4179(3) 0.69993(15) 0.0292(8) Uani 1 1 d . . . . .
C8 C 0.8816(8) 0.5091(3) 0.73932(15) 0.0298(8) Uani 1 1 d . . . . .
C9 C 0.9956(8) 0.3738(3) 0.80762(16) 0.0335(8) Uani 1 1 d . . . . .
H9A H 1.120832 0.319418 0.794541 0.040 Uiso 1 1 calc R U . . .
H9B H 1.113173 0.427463 0.823673 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6476(8) 0.3943(3) 0.87807(15) 0.0310(8) Uani 1 1 d . . . . .
C11 C 0.6660(8) 0.5009(3) 0.87597(16) 0.0337(8) Uani 1 1 d . . . . .
H11 H 0.789261 0.531951 0.851520 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5077(9) 0.5616(3) 0.90888(18) 0.0375(9) Uani 1 1 d . . . . .
H12 H 0.529549 0.633556 0.907645 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3173(10) 0.5192(3) 0.94369(17) 0.0397(9) Uani 1 1 d . . . . .
H13 H 0.204489 0.561578 0.965251 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2949(10) 0.4137(3) 0.94643(16) 0.0364(9) Uani 1 1 d . . . . .
H14 H 0.167195 0.383806 0.970452 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4567(9) 0.3514(3) 0.91451(16) 0.0332(9) Uani 1 1 d . . . . .
C16 C 0.4317(10) 0.2391(3) 0.91895(18) 0.0371(9) Uani 1 1 d . . . . .
Cl1 Cl -0.2911(2) 0.31659(8) 0.53736(4) 0.0382(2) Uani 1 1 d . . . . .
F1 F 0.6760(6) 0.1930(2) 0.93131(11) 0.0448(6) Uani 1 1 d . . . . .
F2 F 0.2505(6) 0.2088(2) 0.95620(12) 0.0528(7) Uani 1 1 d . . . . .
F3 F 0.3475(6) 0.19382(19) 0.87417(11) 0.0461(6) Uani 1 1 d . . . . .
N1 N 0.6372(7) 0.3598(2) 0.73809(13) 0.0320(7) Uani 1 1 d . . . . .
N2 N 0.8394(7) 0.4181(2) 0.76265(13) 0.0313(7) Uani 1 1 d . . . . .
N3 N 0.8157(8) 0.3324(3) 0.84667(14) 0.0341(7) Uani 1 1 d . . . . .
H3A H 0.769(11) 0.268(4) 0.8415(19) 0.035(12) Uiso 1 1 d . . . . .
O1 O 0.6967(6) 0.5088(2) 0.69778(11) 0.0322(6) Uani 1 1 d . . . . .
S1 S 1.0953(2) 0.60315(8) 0.75292(5) 0.0381(2) 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
C1 C2 1.394(6) . ?
C1 C6 1.386(6) . ?
C1 Cl1 1.729(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(6) . ?
C4 C5 1.397(6) . ?
C4 C7 1.466(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(6) . ?
C6 H6 0.9500 . ?
C7 N1 1.290(5) . ?
C7 O1 1.364(5) . ?
C8 N2 1.349(5) . ?
C8 O1 1.380(5) . ?
C8 S1 1.640(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N2 1.487(5) . ?
C9 N3 1.424(6) . ?
C10 C11 1.402(6) . ?
C10 C15 1.419(6) . ?
C10 N3 1.396(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(6) . ?
C15 C16 1.483(6) . ?
C16 F1 1.354(5) . ?
C16 F2 1.346(6) . ?
C16 F3 1.348(5) . ?
N1 N2 1.383(5) . ?
N3 H3A 0.89(5) . ?

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
C2 C1 Cl1 118.7(3) . . ?
C6 C1 C2 121.2(4) . . ?
C6 C1 Cl1 120.0(3) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.1(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 C7 119.5(4) . . ?
C5 C4 C7 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C4 126.3(4) . . ?
N1 C7 O1 114.0(3) . . ?
O1 C7 C4 119.7(3) . . ?
N2 C8 O1 103.8(3) . . ?
N2 C8 S1 131.8(3) . . ?
O1 C8 S1 124.4(3) . . ?
H9A C9 H9B 107.8 . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
N3 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
N3 C9 N2 112.5(3) . . ?
C11 C10 C15 117.4(4) . . ?
N3 C10 C11 121.5(4) . . ?
N3 C10 C15 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.1(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(4) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C16 119.7(4) . . ?
C14 C15 C10 120.6(4) . . ?
C14 C15 C16 119.7(4) . . ?
F1 C16 C15 113.0(4) . . ?
F2 C16 C15 113.5(4) . . ?
F2 C16 F1 105.2(4) . . ?
F2 C16 F3 105.9(4) . . ?
F3 C16 C15 113.4(4) . . ?
F3 C16 F1 105.0(4) . . ?
C7 N1 N2 102.6(3) . . ?
C8 N2 C9 127.6(3) . . ?
C8 N2 N1 113.2(3) . . ?
N1 N2 C9 119.0(3) . . ?
C9 N3 H3A 114(3) . . ?
C10 N3 C9 121.9(4) . . ?
C10 N3 H3A 120(3) . . ?
C7 O1 C8 106.4(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
_geom_hbond_publ_flag
C5 H5 F1 0.95 2.54 3.283(5) 135.7 3_656 yes
N3 H3A F3 0.89(5) 2.39(5) 2.971(5) 123(4) . yes

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 C2 C3 C4 0.6(6) . . . . ?
C2 C1 C6 C5 1.7(7) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C2 C3 C4 C7 -178.9(4) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C3 C4 C7 N1 -5.8(6) . . . . ?
C3 C4 C7 O1 173.8(4) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
C4 C7 N1 N2 180.0(4) . . . . ?
C4 C7 O1 C8 180.0(3) . . . . ?
C5 C4 C7 N1 174.8(4) . . . . ?
C5 C4 C7 O1 -5.7(6) . . . . ?
C6 C1 C2 C3 -1.7(6) . . . . ?
C7 C4 C5 C6 178.9(4) . . . . ?
C7 N1 N2 C8 -0.3(4) . . . . ?
C7 N1 N2 C9 -176.2(3) . . . . ?
C10 C11 C12 C13 -2.5(7) . . . . ?
C10 C15 C16 F1 58.1(5) . . . . ?
C10 C15 C16 F2 177.8(4) . . . . ?
C10 C15 C16 F3 -61.2(5) . . . . ?
C11 C10 C15 C14 0.3(6) . . . . ?
C11 C10 C15 C16 -179.1(4) . . . . ?
C11 C10 N3 C9 -5.8(6) . . . . ?
C11 C12 C13 C14 2.3(7) . . . . ?
C12 C13 C14 C15 -0.9(7) . . . . ?
C13 C14 C15 C10 -0.4(6) . . . . ?
C13 C14 C15 C16 179.0(4) . . . . ?
C14 C15 C16 F1 -121.3(4) . . . . ?
C14 C15 C16 F2 -1.6(6) . . . . ?
C14 C15 C16 F3 119.4(4) . . . . ?
C15 C10 C11 C12 1.2(6) . . . . ?
C15 C10 N3 C9 176.0(4) . . . . ?
Cl1 C1 C2 C3 178.9(3) . . . . ?
Cl1 C1 C6 C5 -178.9(3) . . . . ?
N1 C7 O1 C8 -0.4(4) . . . . ?
N2 C8 O1 C7 0.2(4) . . . . ?
N2 C9 N3 C10 -69.2(5) . . . . ?
N3 C9 N2 C8 133.4(4) . . . . ?
N3 C9 N2 N1 -51.4(5) . . . . ?
N3 C10 C11 C12 -177.1(4) . . . . ?
N3 C10 C15 C14 178.5(4) . . . . ?
N3 C10 C15 C16 -0.9(6) . . . . ?
O1 C7 N1 N2 0.4(4) . . . . ?
O1 C8 N2 C9 175.5(3) . . . . ?
O1 C8 N2 N1 0.0(4) . . . . ?
S1 C8 N2 C9 -4.0(6) . . . . ?
S1 C8 N2 N1 -179.5(3) . . . . ?
S1 C8 O1 C7 179.8(3) . . . . ?

####################################################################### 
# 
# 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_emam-52
_database_code_depnum_ccdc_archive 'CCDC 2302019'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Faculty of Pharmacy, Mansoura University
Egypt
;
_audit_update_record             
;
2023-10-18 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;

_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl F2 N3 O S'
_chemical_formula_sum            'C15 H10 Cl F2 N3 O S'
_chemical_formula_weight         353.77
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   28.8781(9)
_cell_length_b                   13.8936(4)
_cell_length_c                   7.7325(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3102.43(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5035
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.0830
_cell_measurement_theta_min      3.0520
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.686
_exptl_absorpt_coefficient_mu    3.709
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0106
-1 0 0 0.0076
1 -1 0 0.0176
-1 1 0 0.0176
2 0 5 0.0692
-2 0 -5 0.0432

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02

_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15474
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.430
_diffrn_reflns_theta_min         3.061
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -13.00   1.00    7.00    --  -38.50 -57.00   0.00   94
  2  ω    -27.00  64.00   1.00    7.00    --   43.74 -37.00 150.00   91
  3  ω     24.00  95.00   1.00    7.00    --   43.74-121.00 113.00   71
  4  ω     40.00 110.00   1.00   28.00    --  111.00-121.00 113.00   70
  5  ω     61.00 146.00   1.00   28.00    --  111.00 178.00 -90.00   85
  6  ω     43.00 137.00   1.00   28.00    --  111.00 -61.00   0.00   94
  7  ω     90.00 178.00   1.00   28.00    --  111.00  30.00 -60.00   88
  8  ω     38.00 109.00   1.00   28.00    --  111.00-111.00 -60.00   71
  9  ω    104.00 178.00   1.00   28.00    --  111.00 111.00-150.00   74
 10  ω     31.00 107.00   1.00   28.00    --  111.00 -94.00 150.00   76
 11  ω     89.00 178.00   1.00   28.00    --  111.00  45.00-180.00   89
 12  ω     31.00 107.00   1.00   28.00    --  111.00 -94.00-150.00   76
 13  ω     19.00 112.00   1.00    7.00    --   43.74  57.00 150.00   93
 14  ω     19.00 112.00   1.00    7.00    --   43.74  57.00 -90.00   93
 15  ω     71.00 178.00   1.00   28.00    --  111.00  15.00  90.00  107
 16  ω     85.00 178.00   1.00   28.00    --  111.00  61.00   0.00   93
 17  ω     89.00 178.00   1.00   28.00    --  111.00  45.00-120.00   89
 18  ω     31.00  73.00   1.00   28.00    --  111.00 -94.00 -30.00   42
 19  ω    103.00 178.00   1.00   28.00    --  111.00  77.00 120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0220707000
_diffrn_orient_matrix_UB_12      -0.0170183000
_diffrn_orient_matrix_UB_13      -0.1788621000
_diffrn_orient_matrix_UB_21      -0.0479490000
_diffrn_orient_matrix_UB_22      -0.0099004000
_diffrn_orient_matrix_UB_23      0.0856730000
_diffrn_orient_matrix_UB_31      -0.0077831000
_diffrn_orient_matrix_UB_32      0.1090439000
_diffrn_orient_matrix_UB_33      -0.0202224000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2856
_reflns_number_total             3163

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.061
_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)+(0.0258P)²+0.3772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0607
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.55274(9) 0.6584(2) 0.3026(4) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.56608(10) 0.5646(2) 0.3354(4) 0.0338(6) Uani 1 1 d . . . . .
H2 H 0.549058 0.512230 0.288621 0.041 Uiso 1 1 calc R U . . .
C3 C 0.60459(9) 0.5484(2) 0.4372(4) 0.0302(6) Uani 1 1 d . . . . .
H3 H 0.614324 0.484421 0.460703 0.036 Uiso 1 1 calc R U . . .
C4 C 0.62915(9) 0.6258(2) 0.5056(4) 0.0251(5) Uani 1 1 d . . . . .
C5 C 0.61477(9) 0.7196(2) 0.4739(4) 0.0273(6) Uani 1 1 d . . . . .
H5 H 0.631308 0.772251 0.522345 0.033 Uiso 1 1 calc R U . . .
C6 C 0.57629(10) 0.7361(2) 0.3716(4) 0.0305(6) Uani 1 1 d . . . . .
H6 H 0.566175 0.799946 0.349095 0.037 Uiso 1 1 calc R U . . .
C7 C 0.67127(9) 0.6091(2) 0.6059(3) 0.0242(5) Uani 1 1 d . . . . .
C8 C 0.72514(8) 0.52048(19) 0.7261(3) 0.0235(5) Uani 1 1 d . . . . .
C9 C 0.77364(9) 0.6611(2) 0.8266(4) 0.0283(6) Uani 1 1 d . . . . .
H9A H 0.762496 0.705091 0.918376 0.034 Uiso 1 1 calc R U . . .
H9B H 0.793034 0.611135 0.882148 0.034 Uiso 1 1 calc R U . . .
C10 C 0.83675(9) 0.6751(2) 0.6119(4) 0.0274(6) Uani 1 1 d . . . . .
C11 C 0.86389(11) 0.7361(2) 0.5110(4) 0.0319(6) Uani 1 1 d . . . . .
C12 C 0.90084(12) 0.7068(2) 0.4146(5) 0.0407(7) Uani 1 1 d . . . . .
H12 H 0.918378 0.752078 0.349826 0.049 Uiso 1 1 calc R U . . .
C13 C 0.91247(12) 0.6096(3) 0.4127(5) 0.0444(8) Uani 1 1 d . . . . .
H13 H 0.937940 0.586296 0.347194 0.053 Uiso 1 1 calc R U . . .
C14 C 0.88548(12) 0.5490(2) 0.5098(5) 0.0371(7) Uani 1 1 d . . . . .
C15 C 0.84844(10) 0.5778(2) 0.6087(4) 0.0308(6) Uani 1 1 d . . . . .
H15 H 0.831124 0.532282 0.673543 0.037 Uiso 1 1 calc R U . . .
Cl1 Cl 0.50495(2) 0.67872(6) 0.17080(11) 0.04485(19) Uani 1 1 d . . . . .
F1 F 0.85261(8) 0.83169(13) 0.5150(3) 0.0438(5) Uani 1 1 d . . . . .
F2 F 0.89566(9) 0.45284(15) 0.5077(3) 0.0545(6) Uani 1 1 d . . . . .
N1 N 0.69977(7) 0.67096(16) 0.6670(3) 0.0256(4) Uani 1 1 d . . . . .
N2 N 0.73368(7) 0.61487(16) 0.7440(3) 0.0249(5) Uani 1 1 d . . . . .
N3 N 0.80110(8) 0.71385(18) 0.7080(4) 0.0319(6) Uani 1 1 d . . . . .
H3A H 0.7969(11) 0.770(3) 0.709(4) 0.027(9) Uiso 1 1 d . . . . .
O1 O 0.68400(6) 0.51550(13) 0.6380(2) 0.0256(4) Uani 1 1 d . . . . .
S1 S 0.75461(2) 0.42525(5) 0.79013(10) 0.02956(14) 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
C1 C2 1.382(4) . ?
C1 C6 1.383(4) . ?
C1 Cl1 1.739(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 C5 1.390(4) . ?
C4 C7 1.461(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9500 . ?
C7 N1 1.280(4) . ?
C7 O1 1.374(3) . ?
C8 N2 1.342(4) . ?
C8 O1 1.371(3) . ?
C8 S1 1.649(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N2 1.467(3) . ?
C9 N3 1.417(4) . ?
C10 C11 1.394(4) . ?
C10 C15 1.393(4) . ?
C10 N3 1.379(4) . ?
C11 C12 1.364(5) . ?
C11 F1 1.367(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.371(5) . ?
C14 C15 1.374(5) . ?
C14 F2 1.369(4) . ?
C15 H15 0.9500 . ?
N1 N2 1.386(3) . ?
N3 H3A 0.79(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.9(3) . . ?
C2 C1 Cl1 118.8(2) . . ?
C6 C1 Cl1 119.4(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C7 120.2(3) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 C7 119.4(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C4 128.7(3) . . ?
N1 C7 O1 113.4(2) . . ?
O1 C7 C4 117.9(2) . . ?
N2 C8 O1 105.0(2) . . ?
N2 C8 S1 131.2(2) . . ?
O1 C8 S1 123.77(19) . . ?
H9A C9 H9B 107.8 . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
N3 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
N3 C9 N2 112.6(2) . . ?
C15 C10 C11 116.3(3) . . ?
N3 C10 C11 118.9(3) . . ?
N3 C10 C15 124.7(3) . . ?
C12 C11 C10 124.4(3) . . ?
C12 C11 F1 119.3(3) . . ?
F1 C11 C10 116.4(3) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 121.5 . . ?
C14 C13 C12 116.9(3) . . ?
C14 C13 H13 121.5 . . ?
C13 C14 C15 124.6(3) . . ?
F2 C14 C13 118.1(3) . . ?
F2 C14 C15 117.3(3) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 C10 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C7 N1 N2 103.6(2) . . ?
C8 N2 C9 128.1(2) . . ?
C8 N2 N1 112.1(2) . . ?
N1 N2 C9 119.8(2) . . ?
C9 N3 H3A 115(2) . . ?
C10 N3 C9 124.4(2) . . ?
C10 N3 H3A 120(2) . . ?
C8 O1 C7 105.9(2) . . ?

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 C2 C3 C4 0.2(5) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 C7 -176.8(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C3 C4 C7 N1 174.4(3) . . . . ?
C3 C4 C7 O1 -3.6(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C7 N1 N2 -177.8(2) . . . . ?
C4 C7 O1 C8 177.3(2) . . . . ?
C5 C4 C7 N1 -3.3(4) . . . . ?
C5 C4 C7 O1 178.7(2) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
C7 C4 C5 C6 176.7(2) . . . . ?
C7 N1 N2 C8 0.6(3) . . . . ?
C7 N1 N2 C9 178.7(2) . . . . ?
C10 C11 C12 C13 1.1(5) . . . . ?
C11 C10 C15 C14 0.7(4) . . . . ?
C11 C10 N3 C9 -174.4(3) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C12 C13 C14 F2 178.8(3) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?
C15 C10 C11 C12 -1.4(5) . . . . ?
C15 C10 C11 F1 -179.6(3) . . . . ?
C15 C10 N3 C9 5.0(5) . . . . ?
Cl1 C1 C2 C3 178.7(2) . . . . ?
Cl1 C1 C6 C5 -178.9(2) . . . . ?
F1 C11 C12 C13 179.2(3) . . . . ?
F2 C14 C15 C10 -179.2(3) . . . . ?
N1 C7 O1 C8 -1.0(3) . . . . ?
N2 C8 O1 C7 1.3(3) . . . . ?
N2 C9 N3 C10 -87.3(3) . . . . ?
N3 C9 N2 C8 114.8(3) . . . . ?
N3 C9 N2 N1 -62.9(3) . . . . ?
N3 C10 C11 C12 178.0(3) . . . . ?
N3 C10 C11 F1 -0.2(4) . . . . ?
N3 C10 C15 C14 -178.6(3) . . . . ?
O1 C7 N1 N2 0.2(3) . . . . ?
O1 C8 N2 C9 -179.1(2) . . . . ?
O1 C8 N2 N1 -1.2(3) . . . . ?
S1 C8 N2 C9 1.1(4) . . . . ?
S1 C8 N2 N1 178.9(2) . . . . ?
S1 C8 O1 C7 -178.86(19) . . . . ?

