# 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_UJ1
_database_code_depnum_ccdc_archive 'CCDC 2156650'
loop_
_audit_author_name
_audit_author_address
'Gopal Rana'
;Jadavpur University
India
;
_audit_update_record             
;
2022-03-05 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.38 H2.75 N0.25 O0.50 S0.12'
_chemical_formula_weight         58.82

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6868(10)
_cell_length_b                   11.8781(14)
_cell_length_c                   13.2771(15)
_cell_angle_alpha                104.028(3)
_cell_angle_beta                 95.447(3)
_cell_angle_gamma                108.651(3)
_cell_volume                     1237.0(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31655
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.890
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4355
_reflns_number_gt                3265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.1555P)²+3.2245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.1134
_refine_ls_wR_factor_ref         0.3264
_refine_ls_wR_factor_gt          0.3040
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.005

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 0.77402(18) 0.95002(14) 0.72353(11) 0.0377(5) Uani 1 1 d . . . . .
O3 O 0.8263(5) 0.7331(4) 0.2646(3) 0.0436(11) Uani 1 1 d . . . . .
H3 H 0.818972 0.800761 0.267093 0.065 Uiso 1 1 calc R U . . .
O2 O 0.8825(6) 1.0752(4) 0.7687(4) 0.0515(12) Uani 1 1 d . . . . .
O1 O 0.5995(5) 0.9195(5) 0.6953(4) 0.0539(12) Uani 1 1 d . . . . .
N1 N 0.8312(6) 0.8955(4) 0.6097(4) 0.0356(11) Uani 1 1 d . . . . .
N2 N 1.1300(6) 0.9787(5) 0.6611(4) 0.0393(12) Uani 1 1 d . . . . .
C7 C 0.8009(7) 0.7666(5) 0.4459(4) 0.0329(12) Uani 1 1 d . . . . .
C3 C 0.9765(6) 0.8286(5) 0.4923(4) 0.0297(12) Uani 1 1 d . . . . .
C1 C 0.7196(7) 0.8089(5) 0.5203(4) 0.0363(13) Uani 1 1 d . . . . .
H1 H 0.605153 0.783610 0.512843 0.044 Uiso 1 1 calc R U . . .
C2 C 0.9910(6) 0.9054(5) 0.5924(4) 0.0312(12) Uani 1 1 d . . . . .
C8 C 0.7330(7) 0.6809(5) 0.3361(4) 0.0341(13) Uani 1 1 d . . . . .
C15 C 0.7581(7) 0.5571(5) 0.3249(5) 0.0364(13) Uani 1 1 d . . . . .
C00D C 0.8113(7) 0.8595(5) 0.8032(4) 0.0367(13) Uani 1 1 d . . . . .
C5 C 1.2688(7) 0.8984(6) 0.5276(6) 0.0453(15) Uani 1 1 d . . . . .
H5 H 1.368909 0.897565 0.508633 0.054 Uiso 1 1 calc R U . . .
C6 C 1.2672(8) 0.9714(6) 0.6258(6) 0.0476(16) Uani 1 1 d . . . . .
H6 H 1.368488 1.018871 0.670461 0.057 Uiso 1 1 calc R U . . .
C4 C 1.1240(7) 0.8275(5) 0.4585(5) 0.0409(14) Uani 1 1 d . . . . .
H4 H 1.123350 0.780065 0.391416 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5491(8) 0.6579(5) 0.3028(5) 0.0408(14) Uani 1 1 d . . . . .
O1W O 0.5516(10) 0.9207(7) 0.0473(6) 0.118(3) Uani 1 1 d . . . . .
C00J C 0.8710(11) 0.7226(7) 0.9346(5) 0.0586(19) Uani 1 1 d . . . . .
C10 C 0.4288(8) 0.5864(7) 0.3463(6) 0.0575(18) Uani 1 1 d . . . . .
H10 H 0.460647 0.551453 0.396511 0.069 Uiso 1 1 calc R U . . .
C00L C 0.9640(9) 0.8993(7) 0.8686(5) 0.0520(17) Uani 1 1 d . . . . .
H00L H 1.047098 0.972128 0.869227 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4980(9) 0.7068(7) 0.2278(6) 0.0610(19) Uani 1 1 d . . . . .
H14 H 0.576041 0.753172 0.196315 0.073 Uiso 1 1 calc R U . . .
C00N C 0.9910(10) 0.8292(7) 0.9328(6) 0.0607(19) Uani 1 1 d . . . . .
H00N H 1.093949 0.855379 0.976087 0.073 Uiso 1 1 calc R U . . .
C20 C 0.7525(9) 0.4839(6) 0.2251(6) 0.0533(17) Uani 1 1 d . . . . .
H20 H 0.734834 0.511030 0.166449 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7804(10) 0.5123(6) 0.4100(6) 0.0602(19) Uani 1 1 d . . . . .
H16 H 0.782905 0.559164 0.477758 0.072 Uiso 1 1 calc R U . . .
C00Q C 0.6871(9) 0.7521(7) 0.8022(6) 0.0585(19) Uani 1 1 d . . . . .
H00Q H 0.584769 0.725002 0.757976 0.070 Uiso 1 1 calc R U . . .
C19 C 0.7731(11) 0.3694(7) 0.2120(7) 0.071(2) Uani 1 1 d . . . . .
H19 H 0.771599 0.322089 0.144613 0.086 Uiso 1 1 calc R U . . .
C00S C 0.7188(11) 0.6858(7) 0.8688(6) 0.067(2) Uani 1 1 d . . . . .
H00S H 0.635284 0.613907 0.869657 0.080 Uiso 1 1 calc R U . . .
C11 C 0.2625(10) 0.5659(9) 0.3168(7) 0.076(3) Uani 1 1 d . . . . .
H11 H 0.183787 0.518077 0.346964 0.091 Uiso 1 1 calc R U . . .
C00U C 0.8992(14) 0.6475(8) 1.0071(7) 0.088(3) Uani 1 1 d . . . . .
H00A H 0.800987 0.576363 0.996853 0.133 Uiso 1 1 calc R U . . .
H00B H 0.989597 0.620662 0.991240 0.133 Uiso 1 1 calc R U . . .
H00C H 0.924956 0.697922 1.079264 0.133 Uiso 1 1 calc R U . . .
C18 C 0.7951(11) 0.3266(7) 0.2956(8) 0.076(3) Uani 1 1 d . . . . .
H18 H 0.807480 0.250004 0.285855 0.092 Uiso 1 1 calc R U . . .
C13 C 0.2153(10) 0.6170(9) 0.2424(8) 0.081(3) Uani 1 1 d . . . . .
H13 H 0.103838 0.603225 0.221924 0.097 Uiso 1 1 calc R U . . .
C12 C 0.3306(11) 0.6881(9) 0.1979(8) 0.082(3) Uani 1 1 d . . . . .
H12 H 0.298068 0.723511 0.148375 0.099 Uiso 1 1 calc R U . . .
C17 C 0.7991(12) 0.3970(8) 0.3947(8) 0.082(3) Uani 1 1 d . . . . .
H17 H 0.814432 0.367896 0.452555 0.098 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.422(5) . ?
S1 O1 1.430(4) . ?
S1 N1 1.681(5) . ?
S1 C00D 1.757(6) . ?
O3 C8 1.432(7) . ?
N1 C1 1.399(7) . ?
N1 C2 1.402(7) . ?
N2 C2 1.335(7) . ?
N2 C6 1.342(8) . ?
C7 C1 1.359(8) . ?
C7 C3 1.460(8) . ?
C7 C8 1.498(8) . ?
C3 C2 1.386(8) . ?
C3 C4 1.401(8) . ?
C8 C15 1.529(8) . ?
C8 C9 1.533(8) . ?
C15 C16 1.383(9) . ?
C15 C20 1.383(9) . ?
C00D C00Q 1.379(9) . ?
C00D C00L 1.385(9) . ?
C5 C4 1.364(9) . ?
C5 C6 1.384(9) . ?
C9 C14 1.373(9) . ?
C9 C10 1.390(9) . ?
C00J C00N 1.366(11) . ?
C00J C00S 1.388(11) . ?
C00J C00U 1.515(10) . ?
C10 C11 1.386(10) . ?
C00L C00N 1.380(10) . ?
C14 C12 1.401(11) . ?
C20 C19 1.400(10) . ?
C16 C17 1.400(10) . ?
C00Q C00S 1.382(10) . ?
C19 C18 1.350(12) . ?
C11 C13 1.373(13) . ?
C18 C17 1.369(13) . ?
C13 C12 1.370(14) . ?

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 121.2(3) . . ?
O2 S1 N1 106.9(3) . . ?
O1 S1 N1 104.4(2) . . ?
O2 S1 C00D 109.3(3) . . ?
O1 S1 C00D 109.1(3) . . ?
N1 S1 C00D 104.4(2) . . ?
C1 N1 C2 107.5(5) . . ?
C1 N1 S1 123.4(4) . . ?
C2 N1 S1 127.9(4) . . ?
C2 N2 C6 113.2(5) . . ?
C1 C7 C3 105.5(5) . . ?
C1 C7 C8 129.4(5) . . ?
C3 C7 C8 125.0(5) . . ?
C2 C3 C4 116.7(5) . . ?
C2 C3 C7 108.3(5) . . ?
C4 C3 C7 135.0(5) . . ?
C7 C1 N1 110.9(5) . . ?
N2 C2 C3 127.5(5) . . ?
N2 C2 N1 124.7(5) . . ?
C3 C2 N1 107.7(5) . . ?
O3 C8 C7 109.0(4) . . ?
O3 C8 C15 104.3(4) . . ?
C7 C8 C15 111.7(5) . . ?
O3 C8 C9 110.3(5) . . ?
C7 C8 C9 111.5(4) . . ?
C15 C8 C9 109.8(5) . . ?
C16 C15 C20 118.1(6) . . ?
C16 C15 C8 122.8(5) . . ?
C20 C15 C8 119.0(5) . . ?
C00Q C00D C00L 120.9(6) . . ?
C00Q C00D S1 119.8(5) . . ?
C00L C00D S1 119.3(5) . . ?
C4 C5 C6 120.2(6) . . ?
N2 C6 C5 124.6(6) . . ?
C5 C4 C3 117.7(6) . . ?
C14 C9 C10 117.9(6) . . ?
C14 C9 C8 120.7(6) . . ?
C10 C9 C8 121.4(6) . . ?
C00N C00J C00S 117.7(7) . . ?
C00N C00J C00U 121.9(8) . . ?
C00S C00J C00U 120.4(7) . . ?
C11 C10 C9 121.6(8) . . ?
C00N C00L C00D 119.0(7) . . ?
C9 C14 C12 121.3(8) . . ?
C00J C00N C00L 121.9(7) . . ?
C15 C20 C19 120.5(7) . . ?
C15 C16 C17 120.4(7) . . ?
C00D C00Q C00S 118.2(7) . . ?
C18 C19 C20 121.0(8) . . ?
C00Q C00S C00J 122.3(7) . . ?
C13 C11 C10 119.2(8) . . ?
C19 C18 C17 119.4(7) . . ?
C12 C13 C11 120.7(8) . . ?
C13 C12 C14 119.3(9) . . ?
C18 C17 C16 120.6(8) . . ?

_refine_diff_density_max         1.555
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.144


_exptl_crystal_recrystallization_method 'Vapour deposition'
