# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_SP_VS_968_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2k2fjm
_database_code_depnum_ccdc_archive 'CCDC 2355830'
loop_
_audit_author_name
_audit_author_address
'S. Peruncheralathan'
;NISER Bhubaneswar
India
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2024-06-25 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C25 H15 F6 N3 O5 S'
_chemical_formula_sum            'C25 H15 F6 N3 O5 S'
_chemical_formula_weight         583.471
_chemical_oxdiff_formula         'C H N O S F'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.33376 0.55840 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.2215(2)
_cell_length_b                   10.8817(3)
_cell_length_c                   16.0374(6)
_cell_angle_alpha                106.334(3)
_cell_angle_beta                 92.084(3)
_cell_angle_gamma                95.137(2)
_cell_volume                     1202.03(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11366
_cell_measurement_temperature    298.0(7)
_cell_measurement_theta_max      77.6110
_cell_measurement_theta_min      4.1910
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       needle
_exptl_crystal_F_000             595.276
_exptl_crystal_recrystallization_method 'slow diffusion method'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.9984
_diffrn_reflns_Laue_measured_fraction_max 0.9641
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17841
_diffrn_reflns_point_group_measured_fraction_full 0.9984
_diffrn_reflns_point_group_measured_fraction_max 0.9641
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.47
_diffrn_reflns_theta_min         4.26
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.0(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9641
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  15.00   0.50    2.40    --  -38.50 101.00 -13.00  178
  2  ω      7.00  86.00   0.50    2.40    --   49.56-101.00-117.00  158
  3  ω    104.00 175.00   0.50    9.52    --  107.46 101.00 -13.00  142
  4  ω     40.00 107.00   0.50    9.52    --  107.46-101.00-117.00  134
  5  ω   -101.00 -26.00   0.50    2.40    --  -38.50 -59.00 163.80  150
  6  ω   -101.00 -27.00   0.50    2.40    --  -38.50 -58.00-163.32  148
  7  ω    -44.00  31.00   0.50    2.40    --  -38.50  19.00 150.00  150
  8  ω    -86.00  -6.00   0.50    2.40    --  -38.50 125.00  60.00  160
  9  ω   -101.00 -27.00   0.50    2.40    --  -38.50 -57.00-120.00  148
 10  ω    -13.00  61.00   0.50    2.40    --   49.56 -57.00 -90.00  148
 11  ω     38.00 113.00   0.50    2.40    --   49.56  57.00   0.00  150
 12  ω     39.00 107.00   0.50    9.52    --  107.46 -94.00-180.00  136
 13  ω     45.00 113.00   0.50    9.52    --  107.46-125.00  30.00  136
 14  ω    103.00 172.00   0.50    9.52    --  107.46  77.00-120.00  138
 15  ω     99.00 176.00   0.50    9.52    --  107.46  15.00 150.00  154
 16  ω     43.00 131.00   0.50    9.52    --  107.46 -77.00-120.00  176
 17  ω     39.00 116.00   0.50    9.52    --  107.46 -15.00-120.00  154
 18  ω     95.00 170.00   0.50    9.52    --  107.46  60.00  36.09  150
 19  ω     45.00 113.00   0.50    9.52    --  107.46-125.00  60.00  136
 20  ω     43.00 112.00   0.50    9.52    --  107.46 -45.00  90.00  138
 21  ω     43.00 112.00   0.50    9.52    --  107.46 -45.00  30.00  138
 22  ω     43.00 112.00   0.50    9.52    --  107.46 -45.00 150.00  138
 23  ω    103.00 172.00   0.50    9.52    --  107.46  77.00-180.00  138
 24  ω     39.00 107.00   0.50    9.52    --  107.46 -94.00  60.00  136
 25  ω     39.00 107.00   0.50    9.52    --  107.46 -94.00 120.00  136
 26  ω     39.00 107.00   0.50    9.52    --  107.46 -94.00 -30.00  136
 27  ω    103.00 172.00   0.50    9.52    --  107.46  77.00 -30.00  138
 28  ω     45.00 121.00   0.50    9.52    --  107.46 -61.00-120.00  152
 29  ω     43.00 112.00   0.50    9.52    --  107.46 -45.00 -60.00  138
 30  ω     45.00 121.00   0.50    9.52    --  107.46 -61.00  30.00  152
 31  ω     39.00 107.00   0.50    9.52    --  107.46 -94.00 150.00  136
 32  ω     99.00 176.00   0.50    9.52    --  107.46  15.00  90.00  154
 33  ω     38.00 113.00   0.50    2.40    --   49.56  57.00  60.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0191005000
_diffrn_orient_matrix_UB_12      -0.1103875000
_diffrn_orient_matrix_UB_13      0.0427786000
_diffrn_orient_matrix_UB_21      -0.0936897000
_diffrn_orient_matrix_UB_22      -0.0913824000
_diffrn_orient_matrix_UB_23      -0.0855414000
_diffrn_orient_matrix_UB_31      0.1921622000
_diffrn_orient_matrix_UB_32      -0.0382920000
_diffrn_orient_matrix_UB_33      -0.0302401000
_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         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4417
_reflns_number_total             5026
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.9574
_refine_diff_density_min         -1.1371
_refine_diff_density_rms         0.4443
_refine_ls_d_res_high            0.7841
_refine_ls_d_res_low             10.3858
_refine_ls_goodness_of_fit_ref   1.0094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.0094
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1240P)²+0.4801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1848
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C13(H13), C11(H11), C2(H2), C24(H24), C12(H12), C23(H23),
 C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
S1 S 0.27474(8) 0.19320(5) 0.61228(3) 0.04593(19) Uani 1.000000 .
O2 O 0.4519(3) 0.18969(16) 0.19964(11) 0.0555(4) Uani 1.000000 .
O3 O 0.2887(3) 0.00427(16) 0.12596(11) 0.0562(4) Uani 1.000000 .
O5 O 0.3462(3) 0.07640(15) 0.56823(12) 0.0591(5) Uani 1.000000 .
O1 O 0.4575(2) 0.01770(16) 0.25462(10) 0.0528(4) Uani 1.000000 .
N3 N 0.2396(2) 0.57335(16) 0.49032(12) 0.0408(4) Uani 1.000000 .
O4 O 0.0958(3) 0.19112(18) 0.64601(13) 0.0617(5) Uani 1.000000 .
F6 F -0.0097(3) -0.28316(18) 0.08624(16) 0.0969(7) Uani 1.000000 .
N2 N 0.1866(2) 0.47385(17) 0.63748(12) 0.0439(4) Uani 1.000000 .
N1 N 0.2719(3) 0.27830(17) 0.54028(12) 0.0433(4) Uani 1.000000 .
C7 C 0.2643(2) 0.45483(18) 0.48874(13) 0.0373(4) Uani 1.000000 .
F5 F 0.0027(4) -0.1128(2) 0.19149(16) 0.1117(9) Uani 1.000000 .
C1 C 0.3248(3) 0.24339(19) 0.45250(13) 0.0386(4) Uani 1.000000 .
C8 C 0.2357(3) 0.40773(19) 0.56221(14) 0.0392(4) Uani 1.000000 .
F1 F 0.2304(5) -0.1510(3) -0.04768(14) 0.1255(10) Uani 1.000000 .
F2 F 0.4928(4) -0.1572(3) 0.00926(19) 0.1326(11) Uani 1.000000 .
F3 F 0.2850(4) -0.3170(2) -0.01088(16) 0.1130(8) Uani 1.000000 .
C3 C 0.4057(3) 0.1214(2) 0.31846(14) 0.0423(4) Uani 1.000000 .
C14 C 0.1866(3) 0.64769(19) 0.56824(14) 0.0403(4) Uani 1.000000 .
C6 C 0.3204(3) 0.34984(18) 0.41965(13) 0.0378(4) Uani 1.000000 .
C5 C 0.3619(3) 0.3436(2) 0.33388(14) 0.0414(4) Uani 1.000000 .
H5 H 0.3608(3) 0.4139(2) 0.31171(14) 0.0497(5) Uiso 1.000000 R
F4 F -0.0559(3) -0.1052(3) 0.0632(2) 0.1232(9) Uani 1.000000 .
C19 C 0.4367(3) 0.2866(2) 0.69478(14) 0.0472(5) Uani 1.000000 .
C10 C 0.1122(3) 0.6810(2) 0.72004(16) 0.0497(5) Uani 1.000000 .
H10 H 0.0979(3) 0.6501(2) 0.76819(16) 0.0597(6) Uiso 1.000000 R
C13 C 0.1564(3) 0.7771(2) 0.57694(17) 0.0484(5) Uani 1.000000 .
H13 H 0.1709(3) 0.8102(2) 0.52978(17) 0.0581(6) Uiso 1.000000 R
C9 C 0.1624(3) 0.59921(19) 0.64137(14) 0.0416(4) Uani 1.000000 .
C11 C 0.0843(3) 0.8060(2) 0.72606(18) 0.0544(6) Uani 1.000000 .
H11 H 0.0506(3) 0.8594(2) 0.77832(18) 0.0653(7) Uiso 1.000000 R
C4 C 0.4039(3) 0.2256(2) 0.28564(14) 0.0442(5) Uani 1.000000 .
C2 C 0.3674(3) 0.1232(2) 0.40160(14) 0.0435(4) Uani 1.000000 .
H2 H 0.3695(3) 0.0517(2) 0.42235(14) 0.0522(5) Uiso 1.000000 R
C24 C 0.6241(4) 0.2944(3) 0.68034(17) 0.0554(6) Uani 1.000000 .
H24 H 0.6656(4) 0.2466(3) 0.62800(17) 0.0665(7) Uiso 1.000000 R
C15 C 0.4552(4) 0.0565(2) 0.17796(15) 0.0528(5) Uani 1.000000 .
H15 H 0.5641(4) 0.0307(2) 0.14518(15) 0.0634(6) Uiso 1.000000 R
C12 C 0.1059(3) 0.8543(2) 0.65436(18) 0.0537(6) Uani 1.000000 .
H12 H 0.0859(3) 0.9392(2) 0.65926(18) 0.0645(7) Uiso 1.000000 R
C23 C 0.7493(4) 0.3733(3) 0.7441(2) 0.0647(7) Uani 1.000000 .
H23 H 0.8755(4) 0.3780(3) 0.7344(2) 0.0776(8) Uiso 1.000000 R
C16 C 0.2512(4) -0.1302(2) 0.10318(16) 0.0557(6) Uani 1.000000 .
H16 H 0.3192(4) -0.1627(2) 0.14511(16) 0.0669(7) Uiso 1.000000 R
C17 C 0.3148(5) -0.1895(3) 0.0127(2) 0.0778(9) Uani 1.000000 .
C21 C 0.5027(5) 0.4335(3) 0.83582(19) 0.0758(8) Uani 1.000000 .
H21 H 0.4618(5) 0.4794(3) 0.88882(19) 0.0909(10) Uiso 1.000000 R
C20 C 0.3745(4) 0.3556(3) 0.77339(17) 0.0639(7) Uani 1.000000 .
H20 H 0.2486(4) 0.3492(3) 0.78370(17) 0.0767(8) Uiso 1.000000 R
C22 C 0.6907(5) 0.4457(3) 0.8220(2) 0.0673(7) Uani 1.000000 .
C18 C 0.0450(5) -0.1580(3) 0.1101(2) 0.0705(7) Uani 1.000000 .
C25 C 0.8253(6) 0.5387(4) 0.8889(3) 0.0984(12) Uani 1.000000 .
H25a H 0.9503(7) 0.520(2) 0.8764(13) 0.1475(19) Uiso 1.000000 GR
H25b H 0.811(3) 0.6249(5) 0.8873(16) 0.1475(19) Uiso 1.000000 GR
H25c H 0.800(3) 0.531(2) 0.9457(4) 0.1475(19) Uiso 1.000000 GR


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 O5 1.4211(17) . ?
S1 O4 1.4194(18) . ?
S1 N1 1.6717(18) . ?
S1 C19 1.752(2) . ?
O2 C4 1.390(3) . ?
O2 C15 1.395(3) . ?
O3 C15 1.415(3) . ?
O3 C16 1.403(3) . ?
O1 C3 1.384(2) . ?
O1 C15 1.408(3) . ?
N3 C7 1.311(2) . ?
N3 C14 1.372(3) . ?
F6 C18 1.325(3) . ?
N2 C8 1.300(3) . ?
N2 C9 1.375(3) . ?
N1 C1 1.427(3) . ?
N1 C8 1.403(2) . ?
C7 C8 1.426(3) . ?
C7 C6 1.450(3) . ?
F5 C18 1.317(4) . ?
C1 C6 1.403(3) . ?
C1 C2 1.400(3) . ?
F1 C17 1.310(5) . ?
F2 C17 1.309(4) . ?
F3 C17 1.327(4) . ?
C3 C4 1.379(3) . ?
C3 C2 1.366(3) . ?
C14 C13 1.413(3) . ?
C14 C9 1.425(3) . ?
C6 C5 1.402(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.366(3) . ?
F4 C18 1.306(4) . ?
C19 C24 1.380(3) . ?
C19 C20 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.405(3) . ?
C10 C11 1.370(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.371(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.400(4) . ?
C2 H2 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.378(4) . ?
C15 H15 0.9800 . ?
C12 H12 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.381(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.520(4) . ?
C16 C18 1.507(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.376(4) . ?
C21 C22 1.384(5) . ?
C20 H20 0.9300 . ?
C22 C25 1.502(5) . ?
C25 H25a 0.9600 . ?
C25 H25b 0.9600 . ?
C25 H25c 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
O4 S1 O5 120.39(12) . . ?
N1 S1 O5 105.25(10) . . ?
N1 S1 O4 107.50(10) . . ?
C19 S1 O5 110.13(11) . . ?
C19 S1 O4 108.91(11) . . ?
C19 S1 N1 103.22(10) . . ?
C15 O2 C4 105.13(18) . . ?
C16 O3 C15 115.82(19) . . ?
C15 O1 C3 105.12(17) . . ?
C14 N3 C7 114.62(18) . . ?
C9 N2 C8 113.28(18) . . ?
C1 N1 S1 128.71(14) . . ?
C8 N1 S1 123.15(15) . . ?
C8 N1 C1 107.74(16) . . ?
C8 C7 N3 122.16(19) . . ?
C6 C7 N3 130.59(19) . . ?
C6 C7 C8 107.26(17) . . ?
C6 C1 N1 109.16(17) . . ?
C2 C1 N1 128.39(18) . . ?
C2 C1 C6 122.38(19) . . ?
N1 C8 N2 125.49(19) . . ?
C7 C8 N2 125.80(18) . . ?
C7 C8 N1 108.71(18) . . ?
C4 C3 O1 108.92(19) . . ?
C2 C3 O1 126.30(19) . . ?
C2 C3 C4 124.8(2) . . ?
C13 C14 N3 119.2(2) . . ?
C9 C14 N3 122.24(18) . . ?
C9 C14 C13 118.6(2) . . ?
C1 C6 C7 107.14(17) . . ?
C5 C6 C7 130.69(18) . . ?
C5 C6 C1 122.16(18) . . ?
H5 C5 C6 122.81(11) . . ?
C4 C5 C6 114.38(19) . . ?
C4 C5 H5 122.81(13) . . ?
C24 C19 S1 120.01(18) . . ?
C20 C19 S1 119.47(19) . . ?
C20 C19 C24 120.5(2) . . ?
C9 C10 H10 119.88(13) . . ?
C11 C10 H10 119.88(15) . . ?
C11 C10 C9 120.2(2) . . ?
H13 C13 C14 119.73(14) . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.73(14) . . ?
C14 C9 N2 121.89(19) . . ?
C10 C9 N2 118.5(2) . . ?
C10 C9 C14 119.6(2) . . ?
H11 C11 C10 119.66(15) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.66(14) . . ?
C3 C4 O2 109.19(19) . . ?
C5 C4 O2 127.9(2) . . ?
C5 C4 C3 122.9(2) . . ?
C3 C2 C1 113.44(19) . . ?
H2 C2 C1 123.28(12) . . ?
H2 C2 C3 123.28(12) . . ?
H24 C24 C19 120.25(15) . . ?
C23 C24 C19 119.5(2) . . ?
C23 C24 H24 120.25(16) . . ?
O3 C15 O2 105.3(2) . . ?
O1 C15 O2 109.23(18) . . ?
O1 C15 O3 110.5(2) . . ?
H15 C15 O2 110.56(12) . . ?
H15 C15 O3 110.56(12) . . ?
H15 C15 O1 110.56(12) . . ?
C11 C12 C13 120.4(2) . . ?
H12 C12 C13 119.79(14) . . ?
H12 C12 C11 119.79(14) . . ?
H23 C23 C24 119.38(16) . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 H23 119.38(18) . . ?
H16 C16 O3 109.04(13) . . ?
C17 C16 O3 109.8(2) . . ?
C17 C16 H16 109.04(19) . . ?
C18 C16 O3 106.5(2) . . ?
C18 C16 H16 109.04(16) . . ?
C18 C16 C17 113.3(2) . . ?
F2 C17 F1 105.8(3) . . ?
F3 C17 F1 106.8(3) . . ?
F3 C17 F2 108.3(3) . . ?
C16 C17 F1 113.1(3) . . ?
C16 C17 F2 110.8(3) . . ?
C16 C17 F3 111.8(3) . . ?
C20 C21 H21 119.04(17) . . ?
C22 C21 H21 119.04(17) . . ?
C22 C21 C20 121.9(3) . . ?
C21 C20 C19 118.7(3) . . ?
H20 C20 C19 120.65(16) . . ?
H20 C20 C21 120.65(17) . . ?
C21 C22 C23 118.1(3) . . ?
C25 C22 C23 121.2(3) . . ?
C25 C22 C21 120.6(3) . . ?
F5 C18 F6 106.7(3) . . ?
F4 C18 F6 107.6(3) . . ?
F4 C18 F5 107.2(3) . . ?
C16 C18 F6 112.3(3) . . ?
C16 C18 F5 109.9(3) . . ?
C16 C18 F4 112.9(3) . . ?
H25a C25 C22 109.5 . . ?
H25b C25 C22 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 C22 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 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 N1 C1 C6 -173.16(18) . . . . ?
S1 N1 C1 C2 9.7(2) . . . . ?
S1 N1 C8 N2 -5.6(2) . . . . ?
S1 N1 C8 C7 173.59(17) . . . . ?
S1 C19 C24 C23 176.7(2) . . . . ?
S1 C19 C20 C21 -176.7(2) . . . . ?
O2 C4 C3 O1 0.89(19) . . . . ?
O2 C4 C3 C2 179.13(17) . . . . ?
O2 C4 C5 C6 -179.4(2) . . . . ?
O2 C15 O3 C16 -173.78(17) . . . . ?
O2 C15 O1 C3 15.6(2) . . . . ?
O3 C15 O1 C3 -99.82(19) . . . . ?
O3 C16 C17 F1 -60.6(3) . . . . ?
O3 C16 C17 F2 58.0(3) . . . . ?
O3 C16 C17 F3 178.9(3) . . . . ?
O3 C16 C18 F6 177.2(2) . . . . ?
O3 C16 C18 F5 -64.3(2) . . . . ?
O3 C16 C18 F4 55.4(3) . . . . ?
O1 C3 C4 C5 -178.58(16) . . . . ?
O1 C3 C2 C1 177.9(2) . . . . ?
N3 C7 C8 N2 -1.2(2) . . . . ?
N3 C7 C8 N1 179.6(2) . . . . ?
N3 C7 C6 C1 -179.9(2) . . . . ?
N3 C7 C6 C5 -1.2(3) . . . . ?
N3 C14 C13 C12 -179.10(19) . . . . ?
N3 C14 C9 N2 -1.5(2) . . . . ?
N3 C14 C9 C10 178.51(19) . . . . ?
F6 C18 C16 C17 56.3(3) . . . . ?
N2 C8 N1 C1 -178.9(2) . . . . ?
N2 C8 C7 C6 179.0(2) . . . . ?
N2 C9 C14 C13 179.04(19) . . . . ?
N2 C9 C10 C11 -179.1(2) . . . . ?
N1 C1 C6 C7 0.31(17) . . . . ?
N1 C1 C6 C5 -178.51(15) . . . . ?
N1 C1 C2 C3 177.5(2) . . . . ?
N1 C8 C7 C6 -0.15(17) . . . . ?
C7 C6 C1 C2 177.65(15) . . . . ?
C7 C6 C5 C4 -177.7(2) . . . . ?
F5 C18 C16 C17 174.9(3) . . . . ?
C1 C6 C5 C4 0.8(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
F1 C17 C16 C18 58.4(3) . . . . ?
F2 C17 C16 C18 176.9(3) . . . . ?
F3 C17 C16 C18 -62.2(4) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C14 C13 C12 C11 0.2(2) . . . . ?
C14 C9 C10 C11 0.9(2) . . . . ?
F4 C18 C16 C17 -65.5(3) . . . . ?
C19 C24 C23 C22 -0.4(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C24 C23 C22 C21 2.1(3) . . . . ?
C24 C23 C22 C25 -175.6(3) . . . . ?
C23 C22 C21 C20 -2.2(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.828
_oxdiff_exptl_absorpt_empirical_full_min 0.345
####################################################################### 
# 
# 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_vs_900
_audit_block_doi                 10.5517/ccdc.csd.cc2k2fkn
_database_code_depnum_ccdc_archive 'CCDC 2355831'
loop_
_audit_author_name
_audit_author_address
'S. Peruncheralathan'
;NISER Bhubaneswar
India
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2024-06-25 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N3 O2 S'
_chemical_formula_sum            'C21 H15 N3 O2 S'
_chemical_formula_weight         373.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C84 H60 N12 O8 S4 '
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'
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'

_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                   7.9867(2)
_cell_length_b                   18.9604(5)
_cell_length_c                   11.5410(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.527(2)
_cell_angle_gamma                90
_cell_volume                     1728.35(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12739
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.9290
_cell_measurement_theta_min      3.6740
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'slow diffusion method'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19476
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.922
_diffrn_reflns_theta_min         3.516
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  37.00   0.50   25.73    --    7.48 -94.00 150.00  116
  2  ω    -14.00  19.00   0.50   25.73    --   -8.10 -94.00 150.00   66
  3  ω     -3.00  45.00   0.50   25.73    --    7.48  57.00 -30.00   96
  4  ω     -8.00  21.00   0.50   25.73    --    7.48 -99.00 -30.00   58
  5  ω    -43.00  -5.00   0.50   25.73    --   -8.10 -37.00-150.00   76
  6  ω    -74.00 -48.00   0.50   25.73    --   -8.10 -37.00-150.00   52
  7  ω    -73.00  -5.00   0.50   25.73    --   -8.10 -37.00 150.00  136
  8  ω     17.00  43.00   0.50   25.73    --   -8.10  57.00-180.00   52
  9  ω    -31.00   9.00   0.50   25.73    --   -8.10  77.00   0.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0162872000
_diffrn_orient_matrix_UB_12      0.0313248000
_diffrn_orient_matrix_UB_13      0.0333384000
_diffrn_orient_matrix_UB_21      0.0392247000
_diffrn_orient_matrix_UB_22      0.0149916000
_diffrn_orient_matrix_UB_23      -0.0455327000
_diffrn_orient_matrix_UB_31      -0.0790953000
_diffrn_orient_matrix_UB_32      0.0138794000
_diffrn_orient_matrix_UB_33      -0.0260858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4412
_reflns_number_total             4989
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.037
_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)+(0.0514P)²+0.8341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16), C19(H19), C2(H2), C17(H17), C3(H3), C5(H5), C4(H4),
 C10(H10), C13(H13), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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 0.79022(3) 0.33845(2) 0.71984(2) 0.01638(8) Uani 1 1 d . . . . .
O2 O 0.76848(11) 0.34746(5) 0.83985(7) 0.02162(19) Uani 1 1 d . . . . .
O1 O 0.93880(10) 0.30507(5) 0.69145(8) 0.02202(19) Uani 1 1 d . . . . .
N1 N 0.78471(12) 0.41979(5) 0.66348(8) 0.01684(19) Uani 1 1 d . . . . .
N2 N 0.85789(13) 0.38827(5) 0.47398(9) 0.0192(2) Uani 1 1 d . . . . .
N3 N 0.75331(13) 0.53104(6) 0.41315(9) 0.0196(2) Uani 1 1 d . . . . .
C8 C 0.80283(14) 0.43279(6) 0.54551(10) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.74657(14) 0.50315(6) 0.51645(10) 0.0166(2) Uani 1 1 d . . . . .
C20 C 0.63220(14) 0.24829(6) 0.55578(10) 0.0183(2) Uani 1 1 d . . . . .
H20 H 0.741678 0.236660 0.538772 0.022 Uiso 1 1 calc R U . . .
C18 C 0.32696(14) 0.23455(6) 0.51811(10) 0.0186(2) Uani 1 1 d . . . . .
C1 C 0.70603(14) 0.48051(6) 0.70603(10) 0.0171(2) Uani 1 1 d . . . . .
C15 C 0.61223(14) 0.29708(6) 0.64227(10) 0.0158(2) Uani 1 1 d . . . . .
C6 C 0.68436(14) 0.53226(6) 0.61798(10) 0.0174(2) Uani 1 1 d . . . . .
C9 C 0.86351(15) 0.41598(7) 0.36462(10) 0.0195(2) Uani 1 1 d . . . . .
C14 C 0.81498(15) 0.48689(7) 0.33564(10) 0.0196(2) Uani 1 1 d . . . . .
C16 C 0.45263(14) 0.31632(7) 0.66662(10) 0.0182(2) Uani 1 1 d . . . . .
H16 H 0.441203 0.350441 0.725212 0.022 Uiso 1 1 calc R U . . .
C19 C 0.48876(15) 0.21686(6) 0.49464(10) 0.0195(2) Uani 1 1 d . . . . .
H19 H 0.500549 0.182823 0.435987 0.023 Uiso 1 1 calc R U . . .
C2 C 0.65795(16) 0.49303(7) 0.81557(10) 0.0211(2) Uani 1 1 d . . . . .
H2 H 0.673775 0.458453 0.875781 0.025 Uiso 1 1 calc R U . . .
C17 C 0.31064(14) 0.28471(7) 0.60369(10) 0.0196(2) Uani 1 1 d . . . . .
H17 H 0.201133 0.297493 0.619252 0.024 Uiso 1 1 calc R U . . .
C3 C 0.58600(16) 0.55813(7) 0.83293(11) 0.0237(3) Uani 1 1 d . . . . .
H3 H 0.551724 0.567845 0.906688 0.028 Uiso 1 1 calc R U . . .
C5 C 0.61161(16) 0.59728(7) 0.63750(11) 0.0213(2) Uani 1 1 d . . . . .
H5 H 0.596245 0.632208 0.577840 0.026 Uiso 1 1 calc R U . . .
C4 C 0.56221(17) 0.60981(7) 0.74594(12) 0.0240(3) Uani 1 1 d . . . . .
H4 H 0.512090 0.653667 0.761008 0.029 Uiso 1 1 calc R U . . .
C10 C 0.91894(17) 0.37238(8) 0.27824(12) 0.0264(3) Uani 1 1 d . . . . .
H10 H 0.950777 0.324902 0.296249 0.032 Uiso 1 1 calc R U . . .
C13 C 0.82731(17) 0.51255(8) 0.22178(11) 0.0257(3) Uani 1 1 d . . . . .
H13 H 0.797728 0.560039 0.202043 0.031 Uiso 1 1 calc R U . . .
C21 C 0.17338(17) 0.20042(8) 0.44958(12) 0.0279(3) Uani 1 1 d . . . . .
H21A H 0.178216 0.205027 0.365566 0.042 Uiso 1 1 calc R U . . .
H21B H 0.071025 0.223645 0.468193 0.042 Uiso 1 1 calc R U . . .
H21C H 0.170813 0.150353 0.470327 0.042 Uiso 1 1 calc R U . . .
C11 C 0.92661(18) 0.39877(9) 0.16855(12) 0.0316(3) Uani 1 1 d . . . . .
H11 H 0.962818 0.369072 0.110771 0.038 Uiso 1 1 calc R U . . .
C12 C 0.88178(18) 0.46906(9) 0.14014(12) 0.0304(3) Uani 1 1 d . . . . .
H12 H 0.889281 0.486508 0.063914 0.036 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 1.4315(9) . ?
S1 O1 1.4252(9) . ?
S1 N1 1.6717(10) . ?
S1 C15 1.7494(12) . ?
N1 C8 1.4121(14) . ?
N1 C1 1.4329(15) . ?
N2 C8 1.3018(15) . ?
N2 C9 1.3740(15) . ?
N3 C7 1.3126(15) . ?
N3 C14 1.3690(16) . ?
C8 C7 1.4317(16) . ?
C7 C6 1.4481(16) . ?
C20 H20 0.9500 . ?
C20 C15 1.3873(16) . ?
C20 C19 1.3877(17) . ?
C18 C19 1.3998(16) . ?
C18 C17 1.3912(17) . ?
C18 C21 1.5036(17) . ?
C1 C6 1.4046(16) . ?
C1 C2 1.3950(16) . ?
C15 C16 1.3939(15) . ?
C6 C5 1.3954(17) . ?
C9 C14 1.4252(18) . ?
C9 C10 1.4158(17) . ?
C14 C13 1.4182(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3886(17) . ?
C19 H19 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.3887(18) . ?
C17 H17 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.3956(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.3874(17) . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.371(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.371(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.406(2) . ?
C12 H12 0.9500 . ?

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 N1 105.45(5) . . ?
O2 S1 C15 110.04(5) . . ?
O1 S1 O2 120.00(5) . . ?
O1 S1 N1 107.16(5) . . ?
O1 S1 C15 108.92(6) . . ?
N1 S1 C15 104.01(5) . . ?
C8 N1 S1 122.38(8) . . ?
C8 N1 C1 107.64(9) . . ?
C1 N1 S1 126.55(8) . . ?
C8 N2 C9 113.24(11) . . ?
C7 N3 C14 114.48(11) . . ?
N1 C8 C7 108.36(10) . . ?
N2 C8 N1 126.21(11) . . ?
N2 C8 C7 125.41(11) . . ?
N3 C7 C8 122.31(11) . . ?
N3 C7 C6 130.29(11) . . ?
C8 C7 C6 107.40(10) . . ?
C15 C20 H20 120.7 . . ?
C15 C20 C19 118.54(10) . . ?
C19 C20 H20 120.7 . . ?
C19 C18 C21 119.98(11) . . ?
C17 C18 C19 119.18(11) . . ?
C17 C18 C21 120.84(11) . . ?
C6 C1 N1 109.06(10) . . ?
C2 C1 N1 129.86(11) . . ?
C2 C1 C6 121.06(11) . . ?
C20 C15 S1 119.72(8) . . ?
C20 C15 C16 121.72(11) . . ?
C16 C15 S1 118.52(9) . . ?
C1 C6 C7 107.40(10) . . ?
C5 C6 C7 131.94(11) . . ?
C5 C6 C1 120.66(11) . . ?
N2 C9 C14 122.11(11) . . ?
N2 C9 C10 118.67(12) . . ?
C10 C9 C14 119.22(11) . . ?
N3 C14 C9 122.35(11) . . ?
N3 C14 C13 118.48(12) . . ?
C13 C14 C9 119.16(11) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.81(11) . . ?
C17 C16 H16 120.6 . . ?
C20 C19 C18 120.99(11) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.22(12) . . ?
C3 C2 H2 121.4 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.74(11) . . ?
C16 C17 H17 119.6 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.37(11) . . ?
C4 C3 H3 118.8 . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.54(12) . . ?
C4 C5 H5 120.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.14(12) . . ?
C5 C4 H4 119.9 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.90(14) . . ?
C11 C10 H10 120.0 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.22(13) . . ?
C12 C13 H13 119.9 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.10(13) . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.38(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

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 N1 C8 N2 -14.49(16) . . . . ?
S1 N1 C8 C7 164.23(8) . . . . ?
S1 N1 C1 C6 -162.62(8) . . . . ?
S1 N1 C1 C2 19.19(18) . . . . ?
S1 C15 C16 C17 178.71(9) . . . . ?
O2 S1 N1 C8 179.72(9) . . . . ?
O2 S1 N1 C1 -23.81(11) . . . . ?
O2 S1 C15 C20 -142.73(9) . . . . ?
O2 S1 C15 C16 39.64(11) . . . . ?
O1 S1 N1 C8 50.80(10) . . . . ?
O1 S1 N1 C1 -152.74(9) . . . . ?
O1 S1 C15 C20 -9.28(11) . . . . ?
O1 S1 C15 C16 173.09(9) . . . . ?
N1 S1 C15 C20 104.74(10) . . . . ?
N1 S1 C15 C16 -72.90(10) . . . . ?
N1 C8 C7 N3 177.86(10) . . . . ?
N1 C8 C7 C6 -3.01(12) . . . . ?
N1 C1 C6 C7 1.46(13) . . . . ?
N1 C1 C6 C5 -179.35(10) . . . . ?
N1 C1 C2 C3 178.89(12) . . . . ?
N2 C8 C7 N3 -3.41(18) . . . . ?
N2 C8 C7 C6 175.72(11) . . . . ?
N2 C9 C14 N3 -2.69(18) . . . . ?
N2 C9 C14 C13 178.67(11) . . . . ?
N2 C9 C10 C11 -179.67(12) . . . . ?
N3 C7 C6 C1 179.97(11) . . . . ?
N3 C7 C6 C5 0.9(2) . . . . ?
N3 C14 C13 C12 -177.29(12) . . . . ?
C8 N1 C1 C6 -3.34(12) . . . . ?
C8 N1 C1 C2 178.47(11) . . . . ?
C8 N2 C9 C14 0.73(16) . . . . ?
C8 N2 C9 C10 -179.09(11) . . . . ?
C8 C7 C6 C1 0.94(12) . . . . ?
C8 C7 C6 C5 -178.13(12) . . . . ?
C7 N3 C14 C9 1.50(16) . . . . ?
C7 N3 C14 C13 -179.84(10) . . . . ?
C7 C6 C5 C4 179.37(12) . . . . ?
C20 C15 C16 C17 1.13(17) . . . . ?
C1 N1 C8 N2 -174.82(11) . . . . ?
C1 N1 C8 C7 3.90(12) . . . . ?
C1 C6 C5 C4 0.40(18) . . . . ?
C1 C2 C3 C4 -0.28(19) . . . . ?
C15 S1 N1 C8 -64.47(10) . . . . ?
C15 S1 N1 C1 92.00(10) . . . . ?
C15 C20 C19 C18 0.95(18) . . . . ?
C15 C16 C17 C18 0.23(18) . . . . ?
C6 C1 C2 C3 0.89(17) . . . . ?
C6 C5 C4 C3 0.20(19) . . . . ?
C9 N2 C8 N1 -179.35(10) . . . . ?
C9 N2 C8 C7 2.15(16) . . . . ?
C9 C14 C13 C12 1.41(18) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C14 N3 C7 C8 1.27(16) . . . . ?
C14 N3 C7 C6 -177.64(11) . . . . ?
C14 C9 C10 C11 0.51(18) . . . . ?
C14 C13 C12 C11 -0.3(2) . . . . ?
C19 C20 C15 S1 -179.26(9) . . . . ?
C19 C20 C15 C16 -1.70(17) . . . . ?
C19 C18 C17 C16 -0.94(18) . . . . ?
C2 C1 C6 C7 179.84(10) . . . . ?
C2 C1 C6 C5 -0.97(17) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C17 C18 C19 C20 0.35(18) . . . . ?
C10 C9 C14 N3 177.13(11) . . . . ?
C10 C9 C14 C13 -1.52(17) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C21 C18 C19 C20 179.21(11) . . . . ?
C21 C18 C17 C16 -179.80(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.550
_oxdiff_exptl_absorpt_empirical_full_min 0.375
