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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound5aa
_audit_block_doi                 10.5517/ccdc.csd.cc2cxc8y
_database_code_depnum_ccdc_archive 'CCDC 2202000'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 I N2 O2 S'
_chemical_formula_weight         440.29

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.2737(4)
_cell_length_b                   18.0774(6)
_cell_length_c                   16.6031(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.875(8)
_cell_angle_gamma                90.00
_cell_volume                     1734.91(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    297.54(10)
_cell_measurement_reflns_used    6561
_cell_measurement_theta_min      2.2520
_cell_measurement_theta_max      26.6990

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_T_max  0.8269
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297.54(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8461
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2513
_reflns_number_gt                2177
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0631P)²+2.6845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2513
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.09277(9) 0.49080(2) 0.40766(3) 0.0739(3) Uani 1 1 d . . .
S1 S -0.0645(2) 0.48002(8) 0.17041(10) 0.0487(4) Uani 1 1 d . . .
O1 O -0.2101(6) 0.4587(2) 0.2135(3) 0.0637(11) Uani 1 1 d . . .
N1 N 0.0997(7) 0.3089(2) 0.2682(3) 0.0414(10) Uani 1 1 d . . .
O2 O -0.1639(8) 0.5118(2) 0.0854(3) 0.0687(12) Uani 1 1 d . . .
N2 N 0.0709(7) 0.4036(2) 0.1611(3) 0.0456(10) Uani 1 1 d . . .
C1 C 0.2646(9) 0.2786(3) 0.3401(3) 0.0433(13) Uani 1 1 d . . .
C8 C 0.2004(9) 0.3661(2) 0.2400(3) 0.0388(12) Uani 1 1 d . . .
C6 C 0.4741(9) 0.3173(3) 0.3584(3) 0.0452(13) Uani 1 1 d . . .
C7 C 0.4247(9) 0.3729(3) 0.2933(3) 0.0440(12) Uani 1 1 d . . .
H7 H 0.5283 0.4076 0.2884 0.053 Uiso 1 1 calc R . .
C16 C 0.2316(9) 0.5471(3) 0.3282(4) 0.0447(13) Uani 1 1 d . . .
C2 C 0.2566(11) 0.2175(3) 0.3909(4) 0.0567(15) Uani 1 1 d . . .
H2 H 0.1185 0.1925 0.3798 0.068 Uiso 1 1 calc R . .
C13 C 0.4524(10) 0.6248(3) 0.2403(4) 0.0554(15) Uani 1 1 d . . .
H13 H 0.5271 0.6507 0.2104 0.067 Uiso 1 1 calc R . .
C11 C 0.1552(9) 0.5399(3) 0.2371(3) 0.0431(12) Uani 1 1 d . . .
C9 C -0.1365(10) 0.2825(3) 0.2257(4) 0.0582(15) Uani 1 1 d . . .
H9A H -0.2132 0.2859 0.2655 0.087 Uiso 1 1 calc R . .
H9B H -0.1352 0.2319 0.2083 0.087 Uiso 1 1 calc R . .
H9C H -0.2172 0.3122 0.1750 0.087 Uiso 1 1 calc R . .
C12 C 0.2729(10) 0.5798(3) 0.1952(4) 0.0489(13) Uani 1 1 d . . .
H12 H 0.2271 0.5753 0.1350 0.059 Uiso 1 1 calc R . .
C15 C 0.4110(10) 0.5946(3) 0.3723(4) 0.0532(14) Uani 1 1 d . . .
H15 H 0.4551 0.6008 0.4322 0.064 Uiso 1 1 calc R . .
C14 C 0.5270(10) 0.6332(3) 0.3301(4) 0.0537(15) Uani 1 1 d . . .
C3 C 0.4536(13) 0.1959(4) 0.4560(4) 0.0712(19) Uani 1 1 d . . .
H3 H 0.4508 0.1546 0.4890 0.085 Uiso 1 1 calc R . .
C10 C 0.1865(11) 0.4074(3) 0.0980(4) 0.0599(15) Uani 1 1 d . . .
H10A H 0.2194 0.3582 0.0842 0.090 Uiso 1 1 calc R . .
H10B H 0.3283 0.4347 0.1236 0.090 Uiso 1 1 calc R . .
H10C H 0.0864 0.4318 0.0455 0.090 Uiso 1 1 calc R . .
C5 C 0.6731(12) 0.2945(4) 0.4272(4) 0.0623(16) Uani 1 1 d . . .
H5 H 0.8113 0.3199 0.4402 0.075 Uiso 1 1 calc R . .
C4 C 0.6640(13) 0.2339(4) 0.4758(4) 0.0737(19) Uani 1 1 d . . .
H4 H 0.7968 0.2179 0.5218 0.088 Uiso 1 1 calc R . .
C17 C 0.7240(12) 0.6841(4) 0.3801(5) 0.081(2) Uani 1 1 d . . .
H17A H 0.7293 0.6910 0.4382 0.121 Uiso 1 1 calc R . .
H17B H 0.7014 0.7311 0.3509 0.121 Uiso 1 1 calc R . .
H17C H 0.8670 0.6628 0.3831 0.121 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C16 2.104(4) . ?
S1 O1 1.416(4) . ?
S1 O2 1.423(4) . ?
S1 N2 1.661(4) . ?
S1 C11 1.764(6) . ?
N1 C1 1.354(6) . ?
N1 C8 1.385(5) . ?
N1 C9 1.452(7) . ?
N2 C8 1.417(6) . ?
N2 C10 1.490(6) . ?
C1 C2 1.402(7) . ?
C1 C6 1.413(7) . ?
C8 C7 1.345(7) . ?
C6 C5 1.387(8) . ?
C6 C7 1.420(7) . ?
C7 H7 0.9300 . ?
C16 C15 1.377(8) . ?
C16 C11 1.404(7) . ?
C2 C3 1.345(9) . ?
C2 H2 0.9300 . ?
C13 C12 1.355(8) . ?
C13 C14 1.387(8) . ?
C13 H13 0.9300 . ?
C11 C12 1.396(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 H12 0.9300 . ?
C15 C14 1.380(7) . ?
C15 H15 0.9300 . ?
C14 C17 1.506(8) . ?
C3 C4 1.408(10) . ?
C3 H3 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 C4 1.376(9) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.4(3) . . ?
O1 S1 N2 106.0(2) . . ?
O2 S1 N2 106.6(3) . . ?
O1 S1 C11 110.5(2) . . ?
O2 S1 C11 108.0(3) . . ?
N2 S1 C11 105.4(2) . . ?
C1 N1 C8 107.9(4) . . ?
C1 N1 C9 125.5(4) . . ?
C8 N1 C9 126.5(5) . . ?
C8 N2 C10 114.3(4) . . ?
C8 N2 S1 116.2(3) . . ?
C10 N2 S1 115.7(3) . . ?
N1 C1 C2 130.9(5) . . ?
N1 C1 C6 108.5(4) . . ?
C2 C1 C6 120.5(5) . . ?
C7 C8 N1 110.1(4) . . ?
C7 C8 N2 130.0(4) . . ?
N1 C8 N2 119.8(5) . . ?
C5 C6 C1 119.7(5) . . ?
C5 C6 C7 134.2(5) . . ?
C1 C6 C7 106.1(5) . . ?
C8 C7 C6 107.4(4) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C15 C16 C11 119.8(4) . . ?
C15 C16 I1 114.8(4) . . ?
C11 C16 I1 125.4(4) . . ?
C3 C2 C1 118.4(6) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C12 C13 C14 121.3(5) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C12 C11 C16 117.6(5) . . ?
C12 C11 S1 116.1(4) . . ?
C16 C11 S1 126.1(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C12 C11 121.5(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C16 C15 C14 121.9(5) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C14 C13 117.8(5) . . ?
C15 C14 C17 120.8(6) . . ?
C13 C14 C17 121.4(5) . . ?
C2 C3 C4 122.1(6) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 119.4(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.823
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full acta50
_refine_diff_density_max         0.883
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.078
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compound9bh
_audit_block_doi                 10.5517/ccdc.csd.cc2cxcb0
_database_code_depnum_ccdc_archive 'CCDC 2202002'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H22 N2 O2 S'
_chemical_formula_sum            'C19 H22 N2 O2 S'
_chemical_formula_weight         342.44
_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'
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      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                   8.4303(4)
_cell_length_b                   10.1352(5)
_cell_length_c                   11.2583(4)
_cell_angle_alpha                80.979(4)
_cell_angle_beta                 71.424(4)
_cell_angle_gamma                89.642(4)
_cell_volume                     899.57(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6018
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3530
_cell_measurement_theta_min      2.0590
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9699
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.934
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2484
_reflns_number_total             3131
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.083
_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)+(0.0804P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1620
_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:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C17(H17), C14(H14), C6(H6), C15(H15), C7(H7), C4(H4), C16(H16), C5(H5)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.51150(8) 0.40787(7) 0.74400(6) 0.0519(3) Uani 1 1 d . . . . .
O2 O 0.4537(2) 0.28808(19) 0.7171(2) 0.0681(6) Uani 1 1 d . . . . .
O1 O 0.4071(2) 0.4691(2) 0.84452(19) 0.0747(6) Uani 1 1 d . . . . .
N1 N 0.7648(3) 0.1397(2) 0.5843(2) 0.0576(6) Uani 1 1 d . . . . .
N2 N 0.5496(3) 0.5153(2) 0.6156(2) 0.0578(6) Uani 1 1 d . . . . .
C1 C 0.8217(3) 0.2678(2) 0.5798(2) 0.0477(6) Uani 1 1 d . . . . .
C13 C 0.8338(3) 0.3150(2) 0.6954(2) 0.0485(6) Uani 1 1 d . . . . .
C18 C 0.7049(3) 0.3793(2) 0.7746(2) 0.0483(6) Uani 1 1 d . . . . .
C3 C 0.8271(3) 0.2456(3) 0.3834(2) 0.0536(6) Uani 1 1 d . . . . .
C8 C 0.7674(3) 0.1236(3) 0.4651(2) 0.0518(6) Uani 1 1 d . . . . .
C2 C 0.8617(3) 0.3343(3) 0.4593(2) 0.0545(6) Uani 1 1 d . . . . .
H2A H 0.904194 0.422138 0.431140 0.065 Uiso 1 1 calc R . . . .
C17 C 0.7238(4) 0.4248(3) 0.8788(3) 0.0613(7) Uani 1 1 d . . . . .
H17 H 0.637624 0.468558 0.929834 0.074 Uiso 1 1 calc R . . . .
C14 C 0.9798(4) 0.2979(3) 0.7269(3) 0.0632(7) Uani 1 1 d . . . . .
H14 H 1.067435 0.255436 0.675838 0.076 Uiso 1 1 calc R . . . .
C6 C 0.7398(4) 0.0260(3) 0.2949(3) 0.0700(8) Uani 1 1 d . . . . .
H6 H 0.714068 -0.047543 0.263200 0.084 Uiso 1 1 calc R . . . .
C15 C 0.9985(4) 0.3418(3) 0.8310(3) 0.0728(9) Uani 1 1 d . . . . .
H15 H 1.097600 0.328652 0.849951 0.087 Uiso 1 1 calc R . . . .
C7 C 0.7223(4) 0.0139(3) 0.4205(3) 0.0671(8) Uani 1 1 d . . . . .
H7 H 0.681201 -0.065817 0.475238 0.081 Uiso 1 1 calc R . . . .
C4 C 0.8395(4) 0.2544(3) 0.2555(3) 0.0698(8) Uani 1 1 d . . . . .
H4 H 0.877754 0.333860 0.199531 0.084 Uiso 1 1 calc R . . . .
C16 C 0.8705(4) 0.4053(3) 0.9075(3) 0.0741(9) Uani 1 1 d . . . . .
H16 H 0.882903 0.435012 0.978233 0.089 Uiso 1 1 calc R . . . .
C5 C 0.7950(4) 0.1455(3) 0.2133(3) 0.0737(9) Uani 1 1 d . . . . .
H5 H 0.801897 0.151838 0.128495 0.088 Uiso 1 1 calc R . . . .
C19 C 0.6088(5) 0.6518(3) 0.6107(4) 0.0875(10) Uani 1 1 d . . . . .
H19A H 0.539208 0.687085 0.683206 0.131 Uiso 1 1 calc GR . . . .
H19B H 0.603611 0.706529 0.534429 0.131 Uiso 1 1 calc GR . . . .
H19C H 0.722367 0.651476 0.611355 0.131 Uiso 1 1 calc GR . . . .
C9 C 0.6872(4) 0.0415(3) 0.7011(3) 0.0712(8) Uani 1 1 d . . . . .
H9A H 0.650616 0.087863 0.773616 0.085 Uiso 1 1 calc R . . . .
H9B H 0.589473 -0.002450 0.694046 0.085 Uiso 1 1 calc R . . . .
C10 C 0.8058(4) -0.0595(4) 0.7216(3) 0.0800(9) Uani 1 1 d . . . . .
H10A H 0.909024 -0.015926 0.719370 0.096 Uiso 1 1 calc R . . . .
H10B H 0.831942 -0.114008 0.654885 0.096 Uiso 1 1 calc R . . . .
C11 C 0.7244(6) -0.1505(4) 0.8549(4) 0.1011(12) Uani 1 1 d . . . . .
H11A H 0.607698 -0.171294 0.866579 0.121 Uiso 1 1 calc R . . . .
H11B H 0.781169 -0.233959 0.856742 0.121 Uiso 1 1 calc R . . . .
C12 C 0.7354(7) -0.0830(5) 0.9618(4) 0.1241(16) Uani 1 1 d . . . . .
H12A H 0.850652 -0.060664 0.949584 0.186 Uiso 1 1 calc GR . . . .
H12B H 0.688784 -0.142296 1.040947 0.186 Uiso 1 1 calc GR . . . .
H12C H 0.673924 -0.002916 0.963180 0.186 Uiso 1 1 calc GR . . . .
H2 H 0.595(4) 0.476(3) 0.558(3) 0.058(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4213(19) . ?
S1 O1 1.4209(19) . ?
S1 N2 1.610(2) . ?
S1 C18 1.784(2) . ?
N1 C1 1.374(3) . ?
N1 C8 1.371(3) . ?
N1 C9 1.483(4) . ?
N2 C19 1.461(4) . ?
N2 H2 0.80(3) . ?
C1 C13 1.487(3) . ?
C1 C2 1.354(3) . ?
C13 C18 1.399(3) . ?
C13 C14 1.388(4) . ?
C18 C17 1.380(3) . ?
C3 C8 1.408(4) . ?
C3 C2 1.424(4) . ?
C3 C4 1.398(4) . ?
C8 C7 1.391(4) . ?
C2 H2A 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.380(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.360(4) . ?
C6 C5 1.383(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(4) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.470(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.578(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.502(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N2 105.95(13) . . ?
O2 S1 C18 108.89(11) . . ?
O1 S1 O2 119.64(13) . . ?
O1 S1 N2 107.13(14) . . ?
O1 S1 C18 107.05(12) . . ?
N2 S1 C18 107.66(12) . . ?
C1 N1 C9 125.9(2) . . ?
C8 N1 C1 108.9(2) . . ?
C8 N1 C9 124.5(2) . . ?
S1 N2 H2 107(2) . . ?
C19 N2 S1 120.5(2) . . ?
C19 N2 H2 119(2) . . ?
N1 C1 C13 121.4(2) . . ?
C2 C1 N1 109.3(2) . . ?
C2 C1 C13 129.3(2) . . ?
C18 C13 C1 123.1(2) . . ?
C14 C13 C1 119.6(2) . . ?
C14 C13 C18 117.2(2) . . ?
C13 C18 S1 121.55(18) . . ?
C17 C18 S1 117.4(2) . . ?
C17 C18 C13 121.0(2) . . ?
C8 C3 C2 106.4(2) . . ?
C4 C3 C8 118.3(3) . . ?
C4 C3 C2 135.3(3) . . ?
N1 C8 C3 107.6(2) . . ?
N1 C8 C7 131.1(3) . . ?
C7 C8 C3 121.3(3) . . ?
C1 C2 C3 107.8(2) . . ?
C1 C2 H2A 126.1 . . ?
C3 C2 H2A 126.1 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.0 . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C5 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C8 C7 H7 120.8 . . ?
C6 C7 C8 118.4(3) . . ?
C6 C7 H7 120.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 N1 111.3(3) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C9 C10 C11 109.0(3) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 111.7(3) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compound9ba
_audit_block_doi                 10.5517/ccdc.csd.cc2cxc9z
_database_code_depnum_ccdc_archive 'CCDC 2202001'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H16 N2 O2 S'
_chemical_formula_sum            'C16 H16 N2 O2 S'
_chemical_formula_weight         300.37
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6333(5)
_cell_length_b                   11.3408(5)
_cell_length_c                   11.7715(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.2610(19)
_cell_angle_gamma                90
_cell_volume                     1523.13(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8609
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49284
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.251
_diffrn_ambient_temperature      293.23
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2022
_reflns_number_total             2683
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0044(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.053
_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)+(0.0377P)²+1.2416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C10(H10), N2(H2A), C11(H11), C7(H7), C4(H4), C3(H3),
 C12(H12), C5(H5)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.04004(6) 0.09541(6) 0.21551(5) 0.0445(2) Uani 1 1 d . . . . .
N1 N -0.01527(17) 0.38504(17) 0.36439(17) 0.0389(5) Uani 1 1 d . . . . .
C14 C 0.0641(2) 0.0964(2) 0.3483(2) 0.0373(6) Uani 1 1 d . . . . .
O1 O -0.13270(15) 0.17394(17) 0.22623(16) 0.0567(5) Uani 1 1 d . . . . .
C9 C 0.1087(2) 0.2023(2) 0.39904(19) 0.0359(6) Uani 1 1 d . . . . .
C8 C 0.0796(2) 0.3195(2) 0.3453(2) 0.0369(6) Uani 1 1 d . . . . .
C1 C -0.0175(2) 0.4891(2) 0.3033(2) 0.0387(6) Uani 1 1 d . . . . .
O2 O -0.0669(2) -0.02458(17) 0.18725(18) 0.0733(7) Uani 1 1 d . . . . .
C13 C 0.0994(2) -0.0111(2) 0.3992(2) 0.0497(7) Uani 1 1 d . . . . .
H13 H 0.069649 -0.080965 0.363827 0.060 Uiso 1 1 calc R . . . .
C2 C -0.0961(2) 0.5833(2) 0.2955(2) 0.0510(7) Uani 1 1 d . . . . .
H2 H -0.159896 0.581064 0.332304 0.061 Uiso 1 1 calc R . . . .
C10 C 0.1892(2) 0.1959(3) 0.5026(2) 0.0501(7) Uani 1 1 d . . . . .
H10 H 0.220736 0.265157 0.538042 0.060 Uiso 1 1 calc R . . . .
N2 N 0.0223(2) 0.1507(2) 0.11732(18) 0.0566(6) Uani 1 1 d . . . . .
H2A H -0.006149 0.212799 0.080209 0.068 Uiso 1 1 calc R . . . .
C6 C 0.0770(2) 0.4898(2) 0.2461(2) 0.0446(6) Uani 1 1 d . . . . .
C16 C -0.1013(2) 0.3510(3) 0.4323(2) 0.0523(7) Uani 1 1 d . . . . .
H16A H -0.113169 0.415009 0.482158 0.078 Uiso 1 1 calc GR . . . .
H16B H -0.073575 0.283170 0.478390 0.078 Uiso 1 1 calc GR . . . .
H16C H -0.173987 0.332350 0.381430 0.078 Uiso 1 1 calc GR . . . .
C11 C 0.2235(3) 0.0891(3) 0.5541(2) 0.0609(8) Uani 1 1 d . . . . .
H11 H 0.277031 0.086965 0.623932 0.073 Uiso 1 1 calc R . . . .
C7 C 0.1369(2) 0.3804(2) 0.2749(2) 0.0475(7) Uani 1 1 d . . . . .
H7 H 0.203823 0.355533 0.249518 0.057 Uiso 1 1 calc R . . . .
C4 C 0.0186(3) 0.6819(3) 0.1751(3) 0.0680(9) Uani 1 1 d . . . . .
H4 H 0.030096 0.748312 0.132293 0.082 Uiso 1 1 calc R . . . .
C3 C -0.0755(3) 0.6786(3) 0.2317(3) 0.0629(9) Uani 1 1 d . . . . .
H3 H -0.125777 0.742983 0.225934 0.076 Uiso 1 1 calc R . . . .
C12 C 0.1791(3) -0.0138(3) 0.5030(3) 0.0600(8) Uani 1 1 d . . . . .
H12 H 0.202541 -0.085704 0.538007 0.072 Uiso 1 1 calc R . . . .
C5 C 0.0946(3) 0.5890(3) 0.1812(3) 0.0619(8) Uani 1 1 d . . . . .
H5 H 0.157201 0.591780 0.142728 0.074 Uiso 1 1 calc R . . . .
C15 C 0.1272(3) 0.0952(4) 0.0914(3) 0.0886(12) Uani 1 1 d . . . . .
H15A H 0.194117 0.118248 0.148474 0.133 Uiso 1 1 calc GR . . . .
H15B H 0.137937 0.119653 0.016105 0.133 Uiso 1 1 calc GR . . . .
H15C H 0.118655 0.010997 0.092561 0.133 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C14 1.781(2) . ?
S1 O1 1.4228(19) . ?
S1 O2 1.421(2) . ?
S1 N2 1.607(2) . ?
N1 C8 1.385(3) . ?
N1 C1 1.379(3) . ?
N1 C16 1.450(3) . ?
C14 C9 1.395(3) . ?
C14 C13 1.385(3) . ?
C9 C8 1.482(3) . ?
C9 C10 1.386(3) . ?
C8 C7 1.351(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.398(4) . ?
C13 C12 1.382(4) . ?
C2 C3 1.364(4) . ?
C10 C11 1.379(4) . ?
N2 C15 1.458(4) . ?
C6 C7 1.431(3) . ?
C6 C5 1.396(4) . ?
C11 C12 1.367(4) . ?
C4 C3 1.389(4) . ?
C4 C5 1.369(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
O1 S1 C14 108.40(11) . . ?
O1 S1 N2 106.00(13) . . ?
O2 S1 C14 106.99(12) . . ?
O2 S1 O1 118.99(13) . . ?
O2 S1 N2 108.33(14) . . ?
N2 S1 C14 107.67(12) . . ?
C8 N1 C16 127.2(2) . . ?
C1 N1 C8 108.0(2) . . ?
C1 N1 C16 124.8(2) . . ?
C9 C14 S1 120.90(18) . . ?
C13 C14 S1 117.87(19) . . ?
C13 C14 C9 121.2(2) . . ?
C14 C9 C8 123.6(2) . . ?
C10 C9 C14 117.5(2) . . ?
C10 C9 C8 118.8(2) . . ?
N1 C8 C9 122.4(2) . . ?
C7 C8 N1 109.2(2) . . ?
C7 C8 C9 128.4(2) . . ?
N1 C1 C2 129.4(2) . . ?
N1 C1 C6 108.6(2) . . ?
C2 C1 C6 122.0(2) . . ?
C12 C13 C14 119.5(3) . . ?
C3 C2 C1 117.3(3) . . ?
C11 C10 C9 121.3(3) . . ?
C15 N2 S1 119.7(2) . . ?
C1 C6 C7 105.9(2) . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 135.3(3) . . ?
C12 C11 C10 120.3(2) . . ?
C8 C7 C6 108.2(2) . . ?
C5 C4 C3 121.0(3) . . ?
C2 C3 C4 121.7(3) . . ?
C11 C12 C13 120.0(3) . . ?
C4 C5 C6 119.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compound10bk
_audit_block_doi                 10.5517/ccdc.csd.cc2cxcd2
_database_code_depnum_ccdc_archive 'CCDC 2202004'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N2 O2 S'
_chemical_formula_weight         374.44

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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

_cell_length_a                   9.2441(3)
_cell_length_b                   9.3416(3)
_cell_length_c                   21.8748(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.805(3)
_cell_angle_gamma                90.00
_cell_volume                     1884.83(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296.33(10)
_cell_measurement_reflns_used    4722
_cell_measurement_theta_min      2.3320
_cell_measurement_theta_max      21.3800

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16589
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3312
_reflns_number_gt                2026
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.2885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3312
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.00366(9) 0.77017(9) 0.59753(4) 0.0584(3) Uani 1 1 d . . .
O1 O -0.0065(2) 0.8930(2) 0.63646(9) 0.0624(6) Uani 1 1 d . . .
N2 N 0.2670(3) 0.6392(2) 0.71896(10) 0.0496(6) Uani 1 1 d . . .
O2 O -0.1356(2) 0.7208(2) 0.56727(10) 0.0779(7) Uani 1 1 d . . .
N1 N 0.0658(3) 0.6388(2) 0.64090(10) 0.0548(7) Uani 1 1 d . . .
C14 C 0.4082(3) 0.6914(3) 0.72421(12) 0.0476(7) Uani 1 1 d . . .
C9 C 0.4366(3) 0.7589(3) 0.66886(12) 0.0474(7) Uani 1 1 d . . .
C8 C 0.2110(3) 0.6735(3) 0.66099(13) 0.0490(8) Uani 1 1 d . . .
C6 C 0.2745(4) 0.7895(3) 0.56556(13) 0.0523(8) Uani 1 1 d . . .
C7 C 0.3085(3) 0.7449(3) 0.62879(12) 0.0479(7) Uani 1 1 d . . .
C16 C 0.1537(3) 0.6761(3) 0.81700(13) 0.0526(8) Uani 1 1 d . . .
C13 C 0.5098(3) 0.6826(3) 0.77355(13) 0.0591(9) Uani 1 1 d . . .
H13 H 0.4888 0.6365 0.8096 0.071 Uiso 1 1 calc R . .
C1 C 0.1268(3) 0.7981(3) 0.54443(12) 0.0536(8) Uani 1 1 d . . .
C15 C 0.1921(3) 0.5721(3) 0.76794(12) 0.0567(8) Uani 1 1 d . . .
H15A H 0.2533 0.4974 0.7865 0.068 Uiso 1 1 calc R . .
H15B H 0.1040 0.5274 0.7506 0.068 Uiso 1 1 calc R . .
C2 C 0.0857(4) 0.8344(3) 0.48415(14) 0.0672(10) Uani 1 1 d . . .
H2 H -0.0118 0.8364 0.4706 0.081 Uiso 1 1 calc R . .
C21 C 0.2085(4) 0.6617(4) 0.87692(14) 0.0641(9) Uani 1 1 d . . .
H21 H 0.2707 0.5862 0.8875 0.077 Uiso 1 1 calc R . .
C5 C 0.3765(4) 0.8220(3) 0.52375(13) 0.0609(9) Uani 1 1 d . . .
H5 H 0.4747 0.8175 0.5361 0.073 Uiso 1 1 calc R . .
C4 C 0.3352(4) 0.8607(3) 0.46455(14) 0.0703(10) Uani 1 1 d . . .
H4 H 0.4056 0.8826 0.4376 0.084 Uiso 1 1 calc R . .
C10 C 0.5731(4) 0.8217(3) 0.66459(15) 0.0653(9) Uani 1 1 d . . .
H10 H 0.5954 0.8681 0.6288 0.078 Uiso 1 1 calc R . .
C17 C 0.0598(4) 0.7884(3) 0.80281(15) 0.0624(9) Uani 1 1 d . . .
H17 H 0.0210 0.7993 0.7628 0.075 Uiso 1 1 calc R . .
C3 C 0.1907(5) 0.8673(3) 0.44457(14) 0.0741(11) Uani 1 1 d . . .
H3 H 0.1642 0.8941 0.4044 0.089 Uiso 1 1 calc R . .
C11 C 0.6742(4) 0.8145(4) 0.71379(15) 0.0760(10) Uani 1 1 d . . .
H11 H 0.7647 0.8567 0.7112 0.091 Uiso 1 1 calc R . .
C12 C 0.6418(4) 0.7444(4) 0.76734(15) 0.0724(10) Uani 1 1 d . . .
H12 H 0.7120 0.7395 0.7998 0.087 Uiso 1 1 calc R . .
C18 C 0.0229(4) 0.8841(4) 0.84690(18) 0.0767(11) Uani 1 1 d . . .
H18 H -0.0403 0.9591 0.8365 0.092 Uiso 1 1 calc R . .
C22 C 0.0382(4) 0.4907(3) 0.61802(16) 0.0864(12) Uani 1 1 d . . .
H22A H 0.0803 0.4789 0.5794 0.130 Uiso 1 1 calc R . .
H22B H -0.0644 0.4743 0.6129 0.130 Uiso 1 1 calc R . .
H22C H 0.0810 0.4234 0.6470 0.130 Uiso 1 1 calc R . .
C19 C 0.0794(4) 0.8692(4) 0.90630(18) 0.0824(11) Uani 1 1 d . . .
H19 H 0.0548 0.9340 0.9361 0.099 Uiso 1 1 calc R . .
C20 C 0.1723(4) 0.7578(5) 0.92137(16) 0.0783(11) Uani 1 1 d . . .
H20 H 0.2107 0.7472 0.9615 0.094 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.425(2) . ?
S1 O1 1.430(2) . ?
S1 N1 1.655(2) . ?
S1 C1 1.749(3) . ?
N2 C8 1.375(3) . ?
N2 C14 1.391(3) . ?
N2 C15 1.456(3) . ?
N1 C8 1.423(3) . ?
N1 C22 1.487(4) . ?
C14 C13 1.385(4) . ?
C14 C9 1.405(4) . ?
C9 C10 1.400(4) . ?
C9 C7 1.432(4) . ?
C8 C7 1.356(4) . ?
C6 C5 1.390(4) . ?
C6 C1 1.414(4) . ?
C6 C7 1.459(4) . ?
C16 C21 1.380(4) . ?
C16 C17 1.383(4) . ?
C16 C15 1.508(4) . ?
C13 C12 1.365(4) . ?
C13 H13 0.9300 . ?
C1 C2 1.390(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C21 C20 1.381(4) . ?
C21 H21 0.9300 . ?
C5 C4 1.374(4) . ?
C5 H5 0.9300 . ?
C4 C3 1.378(4) . ?
C4 H4 0.9300 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C11 C12 1.392(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C19 C20 1.375(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 O1 119.14(14) . . ?
O2 S1 N1 108.27(13) . . ?
O1 S1 N1 106.00(12) . . ?
O2 S1 C1 110.27(14) . . ?
O1 S1 C1 108.46(14) . . ?
N1 S1 C1 103.49(13) . . ?
C8 N2 C14 106.7(2) . . ?
C8 N2 C15 127.7(3) . . ?
C14 N2 C15 125.4(2) . . ?
C8 N1 C22 116.9(2) . . ?
C8 N1 S1 109.28(19) . . ?
C22 N1 S1 116.47(19) . . ?
C13 C14 N2 128.9(3) . . ?
C13 C14 C9 122.8(3) . . ?
N2 C14 C9 108.3(2) . . ?
C10 C9 C14 117.8(3) . . ?
C10 C9 C7 135.2(3) . . ?
C14 C9 C7 107.0(3) . . ?
C7 C8 N2 111.8(3) . . ?
C7 C8 N1 126.7(3) . . ?
N2 C8 N1 121.4(3) . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 C7 125.0(3) . . ?
C1 C6 C7 118.0(3) . . ?
C8 C7 C9 106.2(2) . . ?
C8 C7 C6 121.6(3) . . ?
C9 C7 C6 132.2(3) . . ?
C21 C16 C17 118.2(3) . . ?
C21 C16 C15 121.6(3) . . ?
C17 C16 C15 120.2(3) . . ?
C12 C13 C14 117.5(3) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 S1 120.6(3) . . ?
C6 C1 S1 117.9(2) . . ?
N2 C15 C16 113.1(2) . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C16 C21 C20 120.9(3) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.049
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compound10al
_audit_block_doi                 10.5517/ccdc.csd.cc2cxcc1
_database_code_depnum_ccdc_archive 'CCDC 2202003'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 N2 O2 S'
_chemical_formula_weight         338.41

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   37.1188(12)
_cell_length_b                   7.4217(2)
_cell_length_c                   11.9822(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3300.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    270(40)
_cell_measurement_reflns_used    8133
_cell_measurement_theta_min      1.9880
_cell_measurement_theta_max      26.4110

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      270(40)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16361
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         24.99
_reflns_number_total             5529
_reflns_number_gt                4228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0756P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.53(9)
_refine_ls_number_reflns         5529
_refine_ls_number_parameters     438
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.57021(3) 0.61779(13) 0.26287(10) 0.0490(3) Uani 1 1 d . . .
S1 S 0.68148(3) 0.18243(15) 0.73953(11) 0.0539(3) Uani 1 1 d . . .
O4 O 0.56498(7) 0.4337(3) 0.2960(3) 0.0546(8) Uani 1 1 d . . .
O3 O 0.56659(8) 0.6646(4) 0.1487(3) 0.0647(9) Uani 1 1 d . . .
N4 N 0.52159(8) 0.7228(4) 0.5288(3) 0.0428(8) Uani 1 1 d . . .
O1 O 0.69432(7) 0.0096(4) 0.7068(3) 0.0643(9) Uani 1 1 d . . .
N1 N 0.72345(8) 0.3537(4) 0.4729(3) 0.0483(9) Uani 1 1 d . . .
N3 N 0.54034(9) 0.7375(4) 0.3343(3) 0.0458(9) Uani 1 1 d . . .
C29 C 0.58211(10) 0.7317(4) 0.4976(4) 0.0381(10) Uani 1 1 d . . .
O2 O 0.68358(9) 0.2319(5) 0.8552(3) 0.0770(10) Uani 1 1 d . . .
C23 C 0.53832(10) 0.7193(5) 0.6328(4) 0.0392(10) Uani 1 1 d . . .
N2 N 0.70544(9) 0.3324(4) 0.6684(3) 0.0494(9) Uani 1 1 d . . .
C36 C 0.54850(11) 0.7293(5) 0.4492(4) 0.0415(10) Uani 1 1 d . . .
C16 C 0.63800(11) 0.2111(5) 0.6895(4) 0.0423(10) Uani 1 1 d . . .
C30 C 0.61441(10) 0.7355(4) 0.4287(4) 0.0389(10) Uani 1 1 d . . .
C12 C 0.59900(9) 0.2524(4) 0.5320(4) 0.0397(10) Uani 1 1 d . . .
H12 H 0.5953 0.2711 0.4561 0.048 Uiso 1 1 calc R . .
C13 C 0.56931(10) 0.2358(5) 0.6033(4) 0.0430(11) Uani 1 1 d . . .
C28 C 0.57605(10) 0.7250(4) 0.6156(4) 0.0391(10) Uani 1 1 d . . .
C11 C 0.63383(10) 0.2412(5) 0.5734(4) 0.0393(10) Uani 1 1 d . . .
C9 C 0.67177(10) 0.2708(5) 0.3869(4) 0.0418(11) Uani 1 1 d . . .
C10 C 0.66587(9) 0.2704(4) 0.5049(4) 0.0399(11) Uani 1 1 d . . .
C8 C 0.65128(11) 0.2278(5) 0.2918(4) 0.0499(12) Uani 1 1 d . . .
H8 H 0.6274 0.1911 0.2994 0.060 Uiso 1 1 calc R . .
C6 C 0.70234(14) 0.2963(6) 0.1752(5) 0.0588(13) Uani 1 1 d . . .
H6 H 0.7120 0.3047 0.1038 0.071 Uiso 1 1 calc R . .
C27 C 0.59829(11) 0.7206(5) 0.7105(4) 0.0469(11) Uani 1 1 d . . .
H27 H 0.6232 0.7246 0.7028 0.056 Uiso 1 1 calc R . .
C32 C 0.67843(10) 0.7929(5) 0.3981(4) 0.0458(11) Uani 1 1 d . . .
C21 C 0.46010(11) 0.8506(6) 0.5139(4) 0.0548(12) Uani 1 1 d . . .
H21 H 0.4685 0.9566 0.4818 0.066 Uiso 1 1 calc R . .
C26 C 0.58302(12) 0.7103(6) 0.8146(5) 0.0538(13) Uani 1 1 d . . .
H26 H 0.5978 0.7082 0.8772 0.065 Uiso 1 1 calc R . .
C24 C 0.52282(11) 0.7072(5) 0.7382(4) 0.0497(11) Uani 1 1 d . . .
H24 H 0.4980 0.7022 0.7472 0.060 Uiso 1 1 calc R . .
C15 C 0.60860(11) 0.1998(5) 0.7593(4) 0.0547(12) Uani 1 1 d . . .
H15 H 0.6118 0.1851 0.8357 0.066 Uiso 1 1 calc R . .
C31 C 0.64850(10) 0.7861(4) 0.4680(4) 0.0414(10) Uani 1 1 d . . .
H31 H 0.6512 0.8161 0.5429 0.050 Uiso 1 1 calc R . .
C35 C 0.61148(10) 0.6938(5) 0.3152(4) 0.0418(10) Uani 1 1 d . . .
C4 C 0.70831(11) 0.3248(5) 0.3696(4) 0.0452(11) Uani 1 1 d . . .
C5 C 0.72341(11) 0.3391(5) 0.2647(5) 0.0541(12) Uani 1 1 d . . .
H5 H 0.7471 0.3767 0.2554 0.065 Uiso 1 1 calc R . .
C38 C 0.71497(10) 0.8470(5) 0.4402(5) 0.0574(13) Uani 1 1 d . . .
H38A H 0.7230 0.9527 0.4012 0.086 Uiso 1 1 calc R . .
H38B H 0.7317 0.7506 0.4278 0.086 Uiso 1 1 calc R . .
H38C H 0.7136 0.8725 0.5187 0.086 Uiso 1 1 calc R . .
C34 C 0.64088(11) 0.7052(5) 0.2428(4) 0.0534(12) Uani 1 1 d . . .
H34 H 0.6383 0.6806 0.1671 0.064 Uiso 1 1 calc R . .
C14 C 0.57448(12) 0.2104(5) 0.7147(4) 0.0521(12) Uani 1 1 d . . .
H14 H 0.5546 0.2000 0.7615 0.063 Uiso 1 1 calc R . .
C7 C 0.66659(13) 0.2401(6) 0.1879(5) 0.0569(13) Uani 1 1 d . . .
H7 H 0.6530 0.2108 0.1252 0.068 Uiso 1 1 calc R . .
C22 C 0.48348(9) 0.6893(5) 0.5066(4) 0.0496(11) Uani 1 1 d . . .
H22A H 0.4748 0.6002 0.5594 0.059 Uiso 1 1 calc R . .
H22B H 0.4812 0.6382 0.4324 0.059 Uiso 1 1 calc R . .
C17 C 0.69793(10) 0.3172(5) 0.5529(4) 0.0429(10) Uani 1 1 d . . .
C33 C 0.67386(11) 0.7539(5) 0.2867(5) 0.0547(13) Uani 1 1 d . . .
H33 H 0.6937 0.7607 0.2394 0.066 Uiso 1 1 calc R . .
C20 C 0.42893(12) 0.8550(7) 0.5614(5) 0.0725(15) Uani 1 1 d . . .
H20A H 0.4196 0.7516 0.5944 0.087 Uiso 1 1 calc R . .
H20B H 0.4158 0.9616 0.5627 0.087 Uiso 1 1 calc R . .
C37 C 0.53307(12) 0.9219(5) 0.2932(4) 0.0632(13) Uani 1 1 d . . .
H37A H 0.5526 0.9999 0.3141 0.095 Uiso 1 1 calc R . .
H37B H 0.5111 0.9655 0.3254 0.095 Uiso 1 1 calc R . .
H37C H 0.5309 0.9199 0.2134 0.095 Uiso 1 1 calc R . .
C19 C 0.70557(13) 0.5184(6) 0.7138(5) 0.0730(15) Uani 1 1 d . . .
H19A H 0.6813 0.5617 0.7192 0.110 Uiso 1 1 calc R . .
H19B H 0.7191 0.5955 0.6650 0.110 Uiso 1 1 calc R . .
H19C H 0.7164 0.5182 0.7865 0.110 Uiso 1 1 calc R . .
C25 C 0.54548(12) 0.7030(5) 0.8282(4) 0.0534(12) Uani 1 1 d . . .
H25 H 0.5358 0.6952 0.8997 0.064 Uiso 1 1 calc R . .
C1 C 0.76168(10) 0.3915(5) 0.4965(5) 0.0586(13) Uani 1 1 d . . .
H1A H 0.7711 0.4692 0.4382 0.070 Uiso 1 1 calc R . .
H1B H 0.7633 0.4570 0.5664 0.070 Uiso 1 1 calc R . .
C2 C 0.78451(12) 0.2303(6) 0.5039(4) 0.0576(13) Uani 1 1 d . . .
H2 H 0.7751 0.1308 0.5410 0.069 Uiso 1 1 calc R . .
C18 C 0.53189(10) 0.2467(6) 0.5537(5) 0.0570(13) Uani 1 1 d . . .
H18A H 0.5225 0.1273 0.5435 0.086 Uiso 1 1 calc R . .
H18B H 0.5330 0.3070 0.4829 0.086 Uiso 1 1 calc R . .
H18C H 0.5164 0.3128 0.6032 0.086 Uiso 1 1 calc R . .
C3 C 0.81659(13) 0.2152(8) 0.4632(5) 0.0810(17) Uani 1 1 d . . .
H3A H 0.8270 0.3115 0.4255 0.097 Uiso 1 1 calc R . .
H3B H 0.8293 0.1080 0.4716 0.097 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O3 1.417(4) . ?
S2 O4 1.436(3) . ?
S2 N3 1.659(3) . ?
S2 C35 1.749(4) . ?
S1 O1 1.423(3) . ?
S1 O2 1.436(4) . ?
S1 N2 1.661(4) . ?
S1 C16 1.735(4) . ?
N4 C36 1.381(5) . ?
N4 C23 1.394(5) . ?
N4 C22 1.460(4) . ?
N1 C17 1.375(5) . ?
N1 C4 1.376(6) . ?
N1 C1 1.474(5) . ?
N3 C36 1.411(6) . ?
N3 C37 1.479(5) . ?
C29 C36 1.376(5) . ?
C29 C28 1.432(6) . ?
C29 C30 1.456(5) . ?
C23 C24 1.390(6) . ?
C23 C28 1.416(5) . ?
N2 C17 1.416(6) . ?
N2 C19 1.483(5) . ?
C16 C15 1.377(6) . ?
C16 C11 1.418(6) . ?
C30 C31 1.401(5) . ?
C30 C35 1.399(6) . ?
C12 C11 1.387(5) . ?
C12 C13 1.400(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(7) . ?
C13 C18 1.513(6) . ?
C28 C27 1.406(6) . ?
C11 C10 1.461(6) . ?
C9 C8 1.407(6) . ?
C9 C4 1.429(5) . ?
C9 C10 1.431(6) . ?
C10 C17 1.367(5) . ?
C8 C7 1.371(7) . ?
C8 H8 0.9300 . ?
C6 C5 1.365(7) . ?
C6 C7 1.400(7) . ?
C6 H6 0.9300 . ?
C27 C26 1.372(6) . ?
C27 H27 0.9300 . ?
C32 C33 1.375(7) . ?
C32 C31 1.393(6) . ?
C32 C38 1.502(6) . ?
C21 C20 1.290(6) . ?
C21 C22 1.481(5) . ?
C21 H21 0.9300 . ?
C26 C25 1.404(6) . ?
C26 H26 0.9300 . ?
C24 C25 1.368(6) . ?
C24 H24 0.9300 . ?
C15 C14 1.376(6) . ?
C15 H15 0.9300 . ?
C31 H31 0.9300 . ?
C35 C34 1.397(6) . ?
C4 C5 1.380(6) . ?
C5 H5 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C34 C33 1.381(6) . ?
C34 H34 0.9300 . ?
C14 H14 0.9300 . ?
C7 H7 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C33 H33 0.9300 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C25 H25 0.9300 . ?
C1 C2 1.469(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.292(6) . ?
C2 H2 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3 H3A 0.9300 . ?
C3 H3B 0.9300 . ?

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
O3 S2 O4 119.1(2) . . ?
O3 S2 N3 107.7(2) . . ?
O4 S2 N3 106.05(18) . . ?
O3 S2 C35 110.5(2) . . ?
O4 S2 C35 109.04(17) . . ?
N3 S2 C35 103.17(19) . . ?
O1 S1 O2 118.6(2) . . ?
O1 S1 N2 106.46(19) . . ?
O2 S1 N2 107.2(2) . . ?
O1 S1 C16 109.09(19) . . ?
O2 S1 C16 110.6(2) . . ?
N2 S1 C16 103.81(19) . . ?
C36 N4 C23 107.2(3) . . ?
C36 N4 C22 125.5(4) . . ?
C23 N4 C22 126.2(4) . . ?
C17 N1 C4 108.4(3) . . ?
C17 N1 C1 124.5(4) . . ?
C4 N1 C1 126.6(4) . . ?
C36 N3 C37 113.8(3) . . ?
C36 N3 S2 109.7(3) . . ?
C37 N3 S2 116.4(3) . . ?
C36 C29 C28 105.8(4) . . ?
C36 C29 C30 120.6(4) . . ?
C28 C29 C30 133.6(4) . . ?
C24 C23 N4 129.0(4) . . ?
C24 C23 C28 122.9(4) . . ?
N4 C23 C28 108.0(4) . . ?
C17 N2 C19 115.7(3) . . ?
C17 N2 S1 110.0(3) . . ?
C19 N2 S1 115.9(3) . . ?
C29 C36 N4 111.4(4) . . ?
C29 C36 N3 127.2(4) . . ?
N4 C36 N3 121.3(4) . . ?
C15 C16 C11 121.2(4) . . ?
C15 C16 S1 121.4(4) . . ?
C11 C16 S1 117.4(3) . . ?
C31 C30 C35 117.1(4) . . ?
C31 C30 C29 124.0(4) . . ?
C35 C30 C29 118.9(4) . . ?
C11 C12 C13 120.7(5) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 C18 121.5(4) . . ?
C12 C13 C18 118.5(5) . . ?
C27 C28 C23 117.5(4) . . ?
C27 C28 C29 135.0(4) . . ?
C23 C28 C29 107.5(4) . . ?
C12 C11 C16 117.5(4) . . ?
C12 C11 C10 123.3(4) . . ?
C16 C11 C10 119.1(4) . . ?
C8 C9 C4 117.4(4) . . ?
C8 C9 C10 135.8(4) . . ?
C4 C9 C10 106.8(4) . . ?
C17 C10 C9 106.4(4) . . ?
C17 C10 C11 120.6(5) . . ?
C9 C10 C11 132.8(4) . . ?
C7 C8 C9 119.7(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C5 C6 C7 121.8(5) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C26 C27 C28 119.6(4) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C33 C32 C31 118.5(4) . . ?
C33 C32 C38 119.6(4) . . ?
C31 C32 C38 121.8(5) . . ?
C20 C21 C22 124.9(4) . . ?
C20 C21 H21 117.5 . . ?
C22 C21 H21 117.5 . . ?
C27 C26 C25 121.2(5) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C25 C24 C23 117.6(4) . . ?
C25 C24 H24 121.2 . . ?
C23 C24 H24 121.2 . . ?
C14 C15 C16 119.4(5) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C32 C31 C30 121.9(4) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C34 C35 C30 122.0(4) . . ?
C34 C35 S2 118.7(4) . . ?
C30 C35 S2 119.2(3) . . ?
N1 C4 C5 129.9(4) . . ?
N1 C4 C9 107.5(4) . . ?
C5 C4 C9 122.6(5) . . ?
C6 C5 C4 117.7(4) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C32 C38 H38A 109.5 . . ?
C32 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C32 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C33 C34 C35 118.1(5) . . ?
C33 C34 H34 120.9 . . ?
C35 C34 H34 120.9 . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N4 C22 C21 114.8(3) . . ?
N4 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
N4 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.5 . . ?
C10 C17 N1 110.9(4) . . ?
C10 C17 N2 127.1(4) . . ?
N1 C17 N2 122.0(4) . . ?
C32 C33 C34 122.3(4) . . ?
C32 C33 H33 118.8 . . ?
C34 C33 H33 118.8 . . ?
C21 C20 H20A 120.0 . . ?
C21 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
N3 C37 H37A 109.5 . . ?
N3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 C25 C26 121.2(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C2 C1 N1 114.3(3) . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
N1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 125.4(5) . . ?
C3 C2 H2 117.3 . . ?
C1 C2 H2 117.3 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compound12ag
_audit_block_doi                 10.5517/ccdc.csd.cc2cxcf3
_database_code_depnum_ccdc_archive 'CCDC 2202005'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H16 N2 O2 S2'
_chemical_formula_sum            'C16 H16 N2 O2 S2'
_chemical_formula_weight         332.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.3674(4)
_cell_length_b                   7.8969(3)
_cell_length_c                   19.6001(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.228(4)
_cell_angle_gamma                90
_cell_volume                     1568.26(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6018
_cell_measurement_temperature    473(200)
_cell_measurement_theta_max      26.3530
_cell_measurement_theta_min      2.0590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12541
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.065
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      473(200)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_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    -53.00 -27.00   0.50    5.00    --  -14.97 -30.00  30.00   52
  2  ω    -35.00  22.00   0.50    5.00    --  -14.97 -94.00  60.00  114
  3  ω    -24.00  19.00   0.50    5.00    --  -14.97 -94.00   0.00   86
  4  ω    -32.00  -7.00   0.50    5.00    --  -14.97 -93.00-107.00   50
  5  ω    -84.00 -56.00   0.50    5.00    --  -14.97 -30.00  30.00   56
  6  ω    -15.00  34.00   0.50    5.00    --  -14.97  93.00   5.00   98
  7  ω     -9.00  17.00   0.50    5.00    --   16.22  93.00   5.00   52
  8  ω    -25.00   5.00   0.50    5.00    --  -14.97  30.00 120.00   60
  9  ω     16.00  56.00   0.50    5.00    --  -14.97  30.00 120.00   80
 10  ω    -36.00 -10.00   0.50    5.00    --   16.22 -94.00 150.00   52
 11  ω     -5.00  53.00   0.50    5.00    --   16.22 -94.00 150.00  116
 12  ω    -34.00  43.00   0.50    5.00    --   16.22 -94.00 120.00  154
 13  ω    -30.00  -4.00   0.50    5.00    --   16.22 -93.00-107.00   52
 14  ω     11.00  42.00   0.50    5.00    --   16.22-125.00-120.00   62
 15  ω    -29.00  -4.00   0.50    5.00    --  -14.97 -94.00-180.00   50
 16  ω    -36.00  44.00   0.50    5.00    --   16.22 -94.00-120.00  160
 17  ω    -59.00 -18.00   0.50    5.00    --  -14.97 125.00-120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0524739000
_diffrn_orient_matrix_UB_12      0.0518776000
_diffrn_orient_matrix_UB_13      -0.0058323000
_diffrn_orient_matrix_UB_21      0.0458726000
_diffrn_orient_matrix_UB_22      -0.0644825000
_diffrn_orient_matrix_UB_23      0.0136502000
_diffrn_orient_matrix_UB_31      -0.0067417000
_diffrn_orient_matrix_UB_32      -0.0348680000
_diffrn_orient_matrix_UB_33      -0.0339176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2083
_reflns_number_total             2772
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0047(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.110
_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)+(0.0622P)²+0.3697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1388
_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. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim S1: within 1.426A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(O1) = Uanis(S1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C12(H12), C5(H5), C4(H4), C11(H11)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.26503(8) 0.29850(9) 0.49293(4) 0.0424(3) Uani 1 1 d . U . . .
S2 S 0.12602(9) -0.02432(11) 0.42726(4) 0.0553(3) Uani 1 1 d . U . . .
O1 O 0.18227(19) 0.4016(2) 0.52535(9) 0.0424(3) Uani 1 1 d . U . . .
N1 N 0.4852(2) 0.2593(3) 0.67197(11) 0.0363(6) Uani 1 1 d . U . . .
O2 O 0.2830(2) 0.3427(3) 0.42510(10) 0.0606(7) Uani 1 1 d . U . . .
N2 N 0.4129(2) 0.2954(3) 0.54633(11) 0.0365(6) Uani 1 1 d . U . . .
C8 C 0.3570(3) 0.0377(3) 0.69040(13) 0.0328(6) Uani 1 1 d . U . . .
C1 C 0.4085(3) 0.2107(3) 0.60952(14) 0.0337(6) Uani 1 1 d . U . . .
C2 C 0.3298(3) 0.0749(3) 0.61718(13) 0.0339(6) Uani 1 1 d . U . . .
C7 C 0.4545(3) 0.1519(3) 0.72273(14) 0.0362(7) Uani 1 1 d . U . . .
C9 C 0.2446(3) 0.0005(3) 0.55649(14) 0.0361(7) Uani 1 1 d . U . . .
C13 C 0.5726(3) 0.4062(3) 0.68595(15) 0.0404(7) Uani 1 1 d . U . . .
H13A H 0.603103 0.433911 0.643801 0.049 Uiso 1 1 calc R . . . .
H13B H 0.649292 0.375929 0.721535 0.049 Uiso 1 1 calc R . . . .
C3 C 0.3074(3) -0.0790(4) 0.73202(14) 0.0425(7) Uani 1 1 d . U . . .
H3 H 0.242494 -0.156066 0.712072 0.051 Uiso 1 1 calc R . . . .
C6 C 0.5063(3) 0.1500(4) 0.79440(14) 0.0434(7) Uani 1 1 d . U . . .
H6 H 0.572989 0.224111 0.814946 0.052 Uiso 1 1 calc R . . . .
C12 C 0.1901(3) -0.1647(4) 0.54753(16) 0.0437(7) Uani 1 1 d . U . . .
H12 H 0.198578 -0.244561 0.583086 0.052 Uiso 1 1 calc R . . . .
C5 C 0.4547(3) 0.0346(4) 0.83313(15) 0.0482(8) Uani 1 1 d . U . . .
H5 H 0.486414 0.031185 0.881181 0.058 Uiso 1 1 calc R . . . .
C10 C 0.2160(3) 0.0894(4) 0.49523(13) 0.0377(7) Uani 1 1 d . U . . .
C4 C 0.3563(3) -0.0777(4) 0.80282(15) 0.0497(8) Uani 1 1 d . U . . .
H4 H 0.322746 -0.153549 0.830971 0.060 Uiso 1 1 calc R . . . .
C16 C 0.5269(3) 0.2574(4) 0.51476(17) 0.0531(9) Uani 1 1 d . U . . .
H16A H 0.606213 0.256840 0.550459 0.080 Uiso 1 1 calc GR . . . .
H16B H 0.533706 0.342306 0.480638 0.080 Uiso 1 1 calc GR . . . .
H16C H 0.515003 0.148381 0.492653 0.080 Uiso 1 1 calc GR . . . .
C14 C 0.5105(3) 0.5593(4) 0.70941(19) 0.0562(9) Uani 1 1 d . U . . .
H14A H 0.471557 0.530430 0.748742 0.067 Uiso 1 1 calc R . . . .
H14B H 0.440709 0.599694 0.671881 0.067 Uiso 1 1 calc R . . . .
C11 C 0.1247(3) -0.1924(4) 0.48148(17) 0.0538(9) Uani 1 1 d . U . . .
H11 H 0.082575 -0.294064 0.466808 0.065 Uiso 1 1 calc R . . . .
C15 C 0.6130(4) 0.6986(4) 0.7307(2) 0.0655(10) Uani 1 1 d . U . . .
H15A H 0.684496 0.656339 0.766009 0.098 Uiso 1 1 calc GR . . . .
H15B H 0.573002 0.793481 0.748809 0.098 Uiso 1 1 calc GR . . . .
H15C H 0.646123 0.733653 0.690763 0.098 Uiso 1 1 calc GR . . . .


_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 O1 1.426(2) . ?
S1 O2 1.424(2) . ?
S1 N2 1.664(2) . ?
S1 C10 1.731(3) . ?
S2 C10 1.711(3) . ?
S2 C11 1.702(3) . ?
N1 C1 1.365(3) . ?
N1 C7 1.394(3) . ?
N1 C13 1.462(3) . ?
N2 C1 1.417(3) . ?
N2 C16 1.476(4) . ?
C8 C2 1.433(3) . ?
C8 C7 1.402(4) . ?
C8 C3 1.399(4) . ?
C1 C2 1.375(4) . ?
C2 C9 1.448(3) . ?
C7 C6 1.394(4) . ?
C9 C12 1.418(4) . ?
C9 C10 1.368(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.488(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.366(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.346(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C4 H4 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.525(4) . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O1 S1 N2 106.83(12) . . ?
O1 S1 C10 109.01(13) . . ?
O2 S1 O1 119.06(13) . . ?
O2 S1 N2 107.79(13) . . ?
O2 S1 C10 110.81(14) . . ?
N2 S1 C10 101.89(12) . . ?
C11 S2 C10 89.91(14) . . ?
C1 N1 C7 107.0(2) . . ?
C1 N1 C13 127.6(2) . . ?
C7 N1 C13 125.1(2) . . ?
C1 N2 S1 111.15(18) . . ?
C1 N2 C16 116.6(2) . . ?
C16 N2 S1 116.90(19) . . ?
C7 C8 C2 106.9(2) . . ?
C3 C8 C2 134.5(3) . . ?
C3 C8 C7 118.6(2) . . ?
N1 C1 N2 122.1(2) . . ?
N1 C1 C2 111.5(2) . . ?
C2 C1 N2 126.4(2) . . ?
C8 C2 C9 134.1(2) . . ?
C1 C2 C8 105.9(2) . . ?
C1 C2 C9 120.0(2) . . ?
N1 C7 C8 108.7(2) . . ?
C6 C7 N1 128.9(3) . . ?
C6 C7 C8 122.4(3) . . ?
C12 C9 C2 129.3(3) . . ?
C10 C9 C2 119.6(3) . . ?
C10 C9 C12 110.9(3) . . ?
N1 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
N1 C13 C14 114.3(2) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C8 C3 H3 120.6 . . ?
C4 C3 C8 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C7 C6 H6 121.5 . . ?
C5 C6 C7 117.0(3) . . ?
C5 C6 H6 121.5 . . ?
C9 C12 H12 124.0 . . ?
C11 C12 C9 112.0(3) . . ?
C11 C12 H12 124.0 . . ?
C6 C5 H5 119.1 . . ?
C6 C5 C4 121.9(3) . . ?
C4 C5 H5 119.1 . . ?
S2 C10 S1 126.54(16) . . ?
C9 C10 S1 120.2(2) . . ?
C9 C10 S2 113.3(2) . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C13 C14 C15 110.4(3) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
S2 C11 H11 123.1 . . ?
C12 C11 S2 113.9(2) . . ?
C12 C11 H11 123.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 5.802
_oxdiff_exptl_absorpt_empirical_full_min 0.438
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
