# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_6362
_database_code_depnum_ccdc_archive 'CCDC 2026878'
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_audit_creation_date             2020-09-01
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H14 N2 O2 S'
_chemical_formula_sum            'C16 H14 N2 O2 S'
_chemical_formula_weight         298.35
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.8959(4)
_cell_length_b                   11.5231(4)
_cell_length_c                   10.6044(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.613(4)
_cell_angle_gamma                90.00
_cell_volume                     1418.54(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2112
_cell_measurement_temperature    112.05(10)
_cell_measurement_theta_max      29.0070
_cell_measurement_theta_min      3.9390
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6321
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.51
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.8432
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
  3 omega   41.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -83.00  -44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  152.0000 -122.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0491023000
_diffrn_orient_matrix_UB_12      -0.0328646000
_diffrn_orient_matrix_UB_13      0.0296116000
_diffrn_orient_matrix_UB_21      0.0357726000
_diffrn_orient_matrix_UB_22      0.0486294000
_diffrn_orient_matrix_UB_23      -0.0035900000
_diffrn_orient_matrix_UB_31      -0.0066467000
_diffrn_orient_matrix_UB_32      0.0185722000
_diffrn_orient_matrix_UB_33      0.0616899000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2328
_reflns_number_total             2785
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.4807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1001
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.24511(4) 0.12309(4) 0.45049(4) 0.01754(15) Uani 1 1 d . . .
O1 O 0.17963(11) 0.19484(12) 0.35046(12) 0.0226(3) Uani 1 1 d . . .
N1 N 0.37334(12) 0.09927(14) 0.42160(14) 0.0178(4) Uani 1 1 d . . .
H1 H 0.4230 0.0813 0.4907 0.021 Uiso 1 1 d R . .
O2 O 0.26858(11) 0.16347(13) 0.58176(12) 0.0229(3) Uani 1 1 d . . .
C14 C 0.01252(16) -0.13547(19) 0.37279(18) 0.0233(5) Uani 1 1 d . . .
H14 H -0.0624 -0.1471 0.3208 0.028 Uiso 1 1 calc R . .
N2 N 0.46987(12) -0.04340(14) 0.32979(14) 0.0183(4) Uani 1 1 d . . .
C2 C 0.32382(15) 0.06925(17) 0.18831(17) 0.0187(4) Uani 1 1 d . . .
H2 H 0.2710 0.1322 0.1777 0.022 Uiso 1 1 calc R . .
C10 C 0.17739(15) -0.01343(17) 0.44271(16) 0.0164(4) Uani 1 1 d . . .
C13 C 0.06539(15) -0.22475(18) 0.45201(17) 0.0203(4) Uani 1 1 d . . .
C1 C 0.38712(15) 0.04104(17) 0.30786(17) 0.0173(4) Uani 1 1 d . . .
C4 C 0.42138(15) -0.08722(17) 0.10140(17) 0.0183(4) Uani 1 1 d . . .
C7 C 0.37182(16) -0.13571(19) -0.12509(18) 0.0232(5) Uani 1 1 d . . .
H7 H 0.3810 -0.1834 -0.1952 0.028 Uiso 1 1 calc R . .
C3 C 0.33812(15) 0.00325(18) 0.08038(17) 0.0179(4) Uani 1 1 d . . .
C8 C 0.29025(16) -0.04493(19) -0.14641(18) 0.0248(5) Uani 1 1 d . . .
H8 H 0.2461 -0.0315 -0.2312 0.030 Uiso 1 1 calc R . .
C12 C 0.17764(16) -0.20753(19) 0.52424(18) 0.0227(4) Uani 1 1 d . . .
H12 H 0.2159 -0.2685 0.5771 0.027 Uiso 1 1 calc R . .
C6 C 0.43759(16) -0.15558(18) -0.00449(18) 0.0221(4) Uani 1 1 d . . .
H6 H 0.4942 -0.2151 0.0085 0.027 Uiso 1 1 calc R . .
C11 C 0.23323(16) -0.10328(18) 0.51953(18) 0.0202(4) Uani 1 1 d . . .
H11 H 0.3095 -0.0927 0.5686 0.024 Uiso 1 1 calc R . .
C5 C 0.48630(16) -0.10296(17) 0.22866(18) 0.0190(4) Uani 1 1 d . . .
H5 H 0.5455 -0.1599 0.2425 0.023 Uiso 1 1 calc R . .
C9 C 0.27379(16) 0.02398(19) -0.04698(17) 0.0218(4) Uani 1 1 d . . .
H9 H 0.2194 0.0856 -0.0631 0.026 Uiso 1 1 calc R . .
C15 C 0.06692(16) -0.02967(18) 0.36810(18) 0.0214(4) Uani 1 1 d . . .
H15 H 0.0292 0.0310 0.3145 0.026 Uiso 1 1 calc R . .
C16 C 0.00463(17) -0.3381(2) 0.4627(2) 0.0288(5) Uani 1 1 d . . .
H16A H -0.0209 -0.3402 0.5445 0.043 Uiso 1 1 calc R . .
H16B H 0.0577 -0.4027 0.4600 0.043 Uiso 1 1 calc R . .
H16C H -0.0623 -0.3451 0.3905 0.043 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 O1 1.4334(13) . ?
S1 N1 1.6432(15) . ?
S1 O2 1.4361(13) . ?
S1 C10 1.761(2) . ?
N1 H1 0.8601 . ?
N1 C1 1.421(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.389(3) . ?
C14 C15 1.386(3) . ?
N2 C1 1.367(2) . ?
N2 C5 1.323(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.365(3) . ?
C2 C3 1.415(3) . ?
C10 C11 1.393(3) . ?
C10 C15 1.391(3) . ?
C13 C12 1.401(3) . ?
C13 C16 1.509(3) . ?
C4 C3 1.422(3) . ?
C4 C6 1.419(3) . ?
C4 C5 1.413(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.411(3) . ?
C7 C6 1.365(3) . ?
C3 C9 1.420(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.368(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.377(3) . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C9 H9 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 N1 109.57(8) . . ?
O1 S1 O2 119.31(9) . . ?
O1 S1 C10 108.15(8) . . ?
N1 S1 C10 106.02(9) . . ?
O2 S1 N1 104.06(8) . . ?
O2 S1 C10 108.96(8) . . ?
S1 N1 H1 112.0 . . ?
C1 N1 S1 121.40(12) . . ?
C1 N1 H1 115.1 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C15 C14 C13 121.32(17) . . ?
C5 N2 C1 117.36(15) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.94(18) . . ?
C3 C2 H2 120.5 . . ?
C11 C10 S1 118.79(14) . . ?
C15 C10 S1 120.84(15) . . ?
C15 C10 C11 120.23(18) . . ?
C14 C13 C12 118.52(19) . . ?
C14 C13 C16 121.70(17) . . ?
C12 C13 C16 119.77(19) . . ?
N2 C1 N1 113.83(15) . . ?
C2 C1 N1 122.24(17) . . ?
C2 C1 N2 123.92(17) . . ?
C6 C4 C3 119.57(17) . . ?
C5 C4 C3 117.43(17) . . ?
C5 C4 C6 122.98(18) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.52(18) . . ?
C2 C3 C4 118.04(16) . . ?
C2 C3 C9 122.96(18) . . ?
C9 C3 C4 119.00(17) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.07(18) . . ?
C9 C8 H8 119.5 . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.77(19) . . ?
C11 C12 H12 119.6 . . ?
C4 C6 H6 120.0 . . ?
C7 C6 C4 119.95(19) . . ?
C7 C6 H6 120.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.86(17) . . ?
C12 C11 H11 120.1 . . ?
N2 C5 C4 124.12(18) . . ?
N2 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C3 C9 H9 120.1 . . ?
C8 C9 C3 119.84(19) . . ?
C8 C9 H9 120.1 . . ?
C14 C15 C10 119.25(19) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 N2 -133.73(14) . . . . ?
S1 N1 C1 C2 47.2(2) . . . . ?
S1 C10 C11 C12 174.00(14) . . . . ?
S1 C10 C15 C14 -174.59(14) . . . . ?
O1 S1 N1 C1 -61.35(17) . . . . ?
O1 S1 C10 C11 171.74(14) . . . . ?
O1 S1 C10 C15 -12.55(17) . . . . ?
N1 S1 C10 C11 54.30(16) . . . . ?
N1 S1 C10 C15 -129.99(15) . . . . ?
O2 S1 N1 C1 169.99(14) . . . . ?
O2 S1 C10 C11 -57.16(16) . . . . ?
O2 S1 C10 C15 118.55(15) . . . . ?
C14 C13 C12 C11 1.7(3) . . . . ?
C2 C3 C9 C8 -178.53(18) . . . . ?
C10 S1 N1 C1 55.13(16) . . . . ?
C13 C14 C15 C10 1.1(3) . . . . ?
C13 C12 C11 C10 0.3(3) . . . . ?
C1 N2 C5 C4 -2.2(3) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
C1 C2 C3 C9 178.15(18) . . . . ?
C4 C3 C9 C8 1.9(3) . . . . ?
C7 C8 C9 C3 -1.0(3) . . . . ?
C3 C2 C1 N1 -176.70(16) . . . . ?
C3 C2 C1 N2 4.3(3) . . . . ?
C3 C4 C6 C7 -1.3(3) . . . . ?
C3 C4 C5 N2 4.0(3) . . . . ?
C8 C7 C6 C4 2.2(3) . . . . ?
C6 C4 C3 C2 179.66(17) . . . . ?
C6 C4 C3 C9 -0.7(3) . . . . ?
C6 C4 C5 N2 -177.30(18) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C11 C10 C15 C14 1.1(3) . . . . ?
C5 N2 C1 N1 178.83(15) . . . . ?
C5 N2 C1 C2 -2.1(3) . . . . ?
C5 C4 C3 C2 -1.6(3) . . . . ?
C5 C4 C3 C9 178.05(17) . . . . ?
C5 C4 C6 C7 -179.99(18) . . . . ?
C15 C14 C13 C12 -2.4(3) . . . . ?
C15 C14 C13 C16 176.98(17) . . . . ?
C15 C10 C11 C12 -1.7(3) . . . . ?
C16 C13 C12 C11 -177.69(17) . . . . ?

