# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_gb_1852_lt_mo
_database_code_depnum_ccdc_archive 'CCDC 2116546'
loop_
_audit_author_name
_audit_author_address
'Goutam Brahmachari'
;Visva Bharati University 
India
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H14 N2 O S'
_chemical_formula_sum            'C22 H14 N2 O S'
_chemical_formula_weight         354.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C88 H56 N8 O4 S4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.9621(4)
_cell_length_b                   8.5724(3)
_cell_length_c                   14.8322(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.399(3)
_cell_angle_gamma                90.00
_cell_volume                     1647.60(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    150.02(18)
_cell_measurement_theta_max      27.9140
_cell_measurement_theta_min      2.7390
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 1 16 0.0706
-6 -11 -7 0.1508
6 11 7 0.1508
13 0 15 0.0721
-14 0 -13 0.0395
6 -10 8 0.1610
1 12 -2 0.1533
-5 8 -15 0.1078
-16 -4 -6 0.0469
-14 -4 12 0.0685
2 3 20 0.0787
12 -1 -16 0.0579

_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.118
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.9427 1.0873 16.0416 -0.0032 -0.0880 1.0316
-6.1186 -10.9002 -6.9468 0.2181 0.9966 -0.0107
6.1186 10.9002 6.9468 -0.2181 -0.9966 0.0107
13.1742 0.0678 15.0063 -0.9908 -0.2805 0.0139
-14.1644 -0.0560 -13.0014 0.9637 0.2726 0.0914
6.0541 -9.8433 8.0559 -0.7123 0.6481 0.0412
1.0313 11.8447 -2.0662 0.2909 -0.9373 -0.1035
-5.1075 7.8285 -15.0591 0.8594 -0.4359 -0.3154
-16.1364 -3.9685 -5.9660 0.7232 0.5438 0.4025
-13.9942 -3.8734 12.0618 0.0564 0.3540 0.9338
2.1672 3.0699 20.0159 -0.6663 -0.4448 0.5992
11.9378 -1.0863 -16.0401 0.0416 0.0988 -0.9937

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5264
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.06
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.02(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  62.00   1.00  110.66    --   26.84 -37.00-180.00   98
  2  ω    -32.00  50.00   1.00  110.66    --   26.84 -60.00 -56.00   82
  3  ω     82.00 119.00   1.00  110.66    --   26.84 178.00   0.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0382393000
_diffrn_orient_matrix_UB_12      0.0222058000
_diffrn_orient_matrix_UB_13      -0.0325559000
_diffrn_orient_matrix_UB_21      -0.0108342000
_diffrn_orient_matrix_UB_22      -0.0797241000
_diffrn_orient_matrix_UB_23      -0.0088224000
_diffrn_orient_matrix_UB_31      -0.0376029000
_diffrn_orient_matrix_UB_32      0.0004589000
_diffrn_orient_matrix_UB_33      0.0339353000
_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              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2722
_reflns_number_total             3561
_reflns_odcompleteness_completeness 98.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.049
_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)+(0.1110P)²+0.4404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2057
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C13(H13), C11(H11), C18(H18), C6(H6), C10(H10), C3(H3), C19(H19),
 C5(H5), C20(H20), C21(H21), C4(H4), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.19707(5) 0.48214(9) 0.74958(4) 0.0222(2) Uani 1 d . . .
O1 O 0.18373(13) 0.2484(3) 0.59908(13) 0.0284(5) Uani 1 d . . .
H1 H 0.1654 0.2121 0.6473 0.043 Uiso 1 calc . . GR
N1 N 0.42100(16) 0.5836(3) 0.75483(14) 0.0202(5) Uani 1 d . . .
N2 N 0.57665(16) 0.4591(3) 0.65211(15) 0.0211(5) Uani 1 d . . .
C15 C 0.27049(19) 0.3076(4) 0.60893(17) 0.0225(6) Uani 1 d . . .
C1 C 0.3952(2) 0.4770(3) 0.69109(17) 0.0189(6) Uani 1 d . . .
C17 C 0.12423(19) 0.6160(3) 0.68147(16) 0.0193(6) Uani 1 d . . .
C2 C 0.52198(19) 0.6282(4) 0.77266(17) 0.0215(6) Uani 1 d . . .
C16 C 0.29488(19) 0.4219(4) 0.67698(17) 0.0195(6) Uani 1 d . . .
C9 C 0.4559(2) 0.3134(4) 0.56161(16) 0.0204(6) Uani 1 d . . .
C8 C 0.48053(19) 0.4192(4) 0.63657(17) 0.0200(6) Uani 1 d . . .
C14 C 0.3542(2) 0.2613(4) 0.54726(17) 0.0212(6) Uani 1 d . . .
C7 C 0.5993(2) 0.5608(4) 0.72089(18) 0.0212(6) Uani 1 d . . .
C22 C 0.01861(19) 0.6247(4) 0.69414(19) 0.0254(7) Uani 1 d . . .
H22 H -0.0126 0.5596 0.7355 0.030 Uiso 1 calc . . R
C13 C 0.3309(2) 0.1634(4) 0.47479(18) 0.0270(7) Uani 1 d . . .
H13 H 0.2636 0.1280 0.4655 0.032 Uiso 1 calc . . R
C11 C 0.5080(2) 0.1694(4) 0.43086(18) 0.0280(7) Uani 1 d . . .
H11 H 0.5591 0.1385 0.3917 0.034 Uiso 1 calc . . R
C18 C 0.1703(2) 0.7163(4) 0.62064(18) 0.0243(6) Uani 1 d . . .
H18 H 0.2411 0.7119 0.6125 0.029 Uiso 1 calc . . R
C6 C 0.7032(2) 0.6014(4) 0.73977(19) 0.0268(7) Uani 1 d . . .
H6 H 0.7554 0.5578 0.7060 0.032 Uiso 1 calc . . R
C10 C 0.5328(2) 0.2653(4) 0.50247(17) 0.0232(6) Uani 1 d . . .
H10 H 0.6006 0.2983 0.5118 0.028 Uiso 1 calc . . R
C3 C 0.5469(2) 0.7362(4) 0.84048(18) 0.0241(6) Uani 1 d . . .
H3 H 0.4954 0.7822 0.8740 0.029 Uiso 1 calc . . R
C19 C 0.1109(2) 0.8217(4) 0.57267(19) 0.0285(7) Uani 1 d . . .
H19 H 0.1421 0.8894 0.5327 0.034 Uiso 1 calc . . R
C5 C 0.7272(2) 0.7037(4) 0.8068(2) 0.0295(7) Uani 1 d . . .
H5 H 0.7960 0.7279 0.8197 0.035 Uiso 1 calc . . R
C20 C 0.0052(2) 0.8281(4) 0.5832(2) 0.0312(7) Uani 1 d . . .
H20 H -0.0348 0.8973 0.5490 0.037 Uiso 1 calc . . R
C21 C -0.0401(2) 0.7313(4) 0.6447(2) 0.0294(7) Uani 1 d . . .
H21 H -0.1109 0.7372 0.6531 0.035 Uiso 1 calc . . R
C4 C 0.6488(2) 0.7733(4) 0.8569(2) 0.0287(7) Uani 1 d . . .
H4 H 0.6661 0.8454 0.9016 0.034 Uiso 1 calc . . R
C12 C 0.4072(2) 0.1182(4) 0.41644(19) 0.0302(7) Uani 1 d . . .
H12 H 0.3910 0.0538 0.3677 0.036 Uiso 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 C17 1.784(3) . ?
S1 C16 1.761(3) . ?
O1 H1 0.8200 . ?
O1 C15 1.239(3) . ?
N1 C1 1.351(4) . ?
N1 C2 1.383(3) . ?
N2 C8 1.307(3) . ?
N2 C7 1.368(4) . ?
C15 C16 1.436(4) . ?
C15 C14 1.490(4) . ?
C1 C16 1.395(4) . ?
C1 C8 1.472(4) . ?
C17 C22 1.388(4) . ?
C17 C18 1.391(4) . ?
C2 C7 1.402(4) . ?
C2 C3 1.399(4) . ?
C9 C8 1.464(4) . ?
C9 C14 1.403(4) . ?
C9 C10 1.406(4) . ?
C14 C13 1.392(4) . ?
C7 C6 1.412(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.387(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.375(4) . ?
C11 C12 1.391(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.356(4) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.407(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C4 H4 0.9300 . ?
C12 H12 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
C16 S1 C17 102.80(12) . . ?
C15 O1 H1 109.5 . . ?
C1 N1 C2 122.5(2) . . ?
C8 N2 C7 119.0(2) . . ?
O1 C15 C16 123.1(2) . . ?
O1 C15 C14 119.4(3) . . ?
C16 C15 C14 117.5(2) . . ?
N1 C1 C16 123.2(2) . . ?
N1 C1 C8 115.9(2) . . ?
C16 C1 C8 120.9(3) . . ?
C22 C17 S1 117.9(2) . . ?
C22 C17 C18 119.6(3) . . ?
C18 C17 S1 122.4(2) . . ?
N1 C2 C7 117.9(3) . . ?
N1 C2 C3 121.4(2) . . ?
C3 C2 C7 120.7(2) . . ?
C15 C16 S1 118.72(19) . . ?
C1 C16 S1 119.4(2) . . ?
C1 C16 C15 121.7(2) . . ?
C14 C9 C8 119.9(2) . . ?
C14 C9 C10 119.4(3) . . ?
C10 C9 C8 120.7(2) . . ?
N2 C8 C1 122.7(3) . . ?
N2 C8 C9 119.0(2) . . ?
C9 C8 C1 118.2(2) . . ?
C9 C14 C15 121.2(3) . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 C9 119.7(2) . . ?
N2 C7 C2 121.8(2) . . ?
N2 C7 C6 119.4(2) . . ?
C2 C7 C6 118.7(3) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.4(3) . . ?
C21 C20 H20 120.3 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?

_olex2_date_sample_data_collection 2021-04-09
_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 4.454
_oxdiff_exptl_absorpt_empirical_full_min 0.649
