# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2064571'
loop_
_audit_author_name
_audit_author_address
'Manash Protim Gogoi'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-02-23 deposited with the CCDC.	2021-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O2 S'
_chemical_formula_weight         351.45

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   6.1683(9)
_cell_length_b                   18.221(3)
_cell_length_c                   8.3375(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.838(5)
_cell_angle_gamma                90
_cell_volume                     920.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.46

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ccd area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16985
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.487
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4130
_reflns_number_gt                3877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.982

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.0687P] 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_abs_structure_details 
;
 Flack x determined using 1771 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4130
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_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
S001 S 0.59706(9) 0.39019(3) 0.78052(6) 0.04727(15) Uani 1 1 d . . . . .
N002 N 0.6792(3) 0.53012(8) 0.68844(18) 0.0344(3) Uani 1 1 d . . . . .
O003 O 0.8167(3) 0.60136(10) 0.5177(2) 0.0626(5) Uani 1 1 d . . . . .
O004 O 1.0472(3) 0.56348(10) 0.7423(2) 0.0572(4) Uani 1 1 d . . . . .
C2 C 0.7179(3) 0.50655(10) 0.9776(2) 0.0309(3) Uani 1 1 d . . . . .
C006 C 0.6792(3) 0.48262(10) 0.8232(2) 0.0319(3) Uani 1 1 d . . . . .
C007 C 0.9446(3) 0.38675(13) 0.6062(2) 0.0414(4) Uani 1 1 d . . . . .
H007 H 1.012584 0.424753 0.671396 0.050 Uiso 1 1 calc R U . . .
C008 C 0.7332(3) 0.58642(10) 1.0193(2) 0.0317(4) Uani 1 1 d . . . . .
C009 C 0.9509(4) 0.29846(11) 0.3885(2) 0.0435(5) Uani 1 1 d . . . . .
C00A C 0.5537(3) 0.63319(11) 0.9737(2) 0.0422(4) Uani 1 1 d . . . . .
H00A H 0.424625 0.615491 0.909319 0.051 Uiso 1 1 calc R U . . .
C00B C 0.8649(4) 0.56441(11) 0.6607(2) 0.0414(4) Uani 1 1 d . . . . .
C00C C 0.6471(4) 0.30057(10) 0.5339(2) 0.0409(4) Uani 1 1 d . . . . .
H00C H 0.512194 0.281701 0.548795 0.049 Uiso 1 1 calc R U . . .
C00D C 1.0445(4) 0.35684(12) 0.4848(3) 0.0442(4) Uani 1 1 d . . . . .
H00D H 1.177427 0.376428 0.467456 0.053 Uiso 1 1 calc R U . . .
C00E C 0.7532(4) 0.27037(11) 0.4169(3) 0.0452(5) Uani 1 1 d . . . . .
H00E H 0.690053 0.230360 0.356271 0.054 Uiso 1 1 calc R U . . .
C00F C 0.7429(3) 0.35944(10) 0.6294(2) 0.0366(4) Uani 1 1 d . . . . .
C00G C 0.7371(3) 0.45383(11) 1.1197(2) 0.0387(4) Uani 1 1 d . . . . .
H00B H 0.809841 0.409529 1.092783 0.046 Uiso 1 1 calc R U . . .
H00F H 0.830592 0.475874 1.213948 0.046 Uiso 1 1 calc R U . . .
C00H C 0.5831(5) 0.59636(15) 0.4529(3) 0.0603(6) Uani 1 1 d . . . . .
H00G H 0.557361 0.583042 0.338237 0.072 Uiso 1 1 calc R U . . .
H00H H 0.511110 0.642912 0.464138 0.072 Uiso 1 1 calc R U . . .
C00I C 0.4957(4) 0.53726(15) 0.5523(3) 0.0524(5) Uani 1 1 d . . . . .
H00I H 0.362190 0.552896 0.588096 0.063 Uiso 1 1 calc R U . . .
H00J H 0.467547 0.491749 0.491620 0.063 Uiso 1 1 calc R U . . .
C00J C 0.7567(5) 0.73320(13) 1.1165(3) 0.0572(6) Uani 1 1 d . . . . .
H00K H 0.764403 0.782158 1.148597 0.069 Uiso 1 1 calc R U . . .
C00K C 0.5657(4) 0.70595(13) 1.0235(3) 0.0551(6) Uani 1 1 d . . . . .
H00L H 0.443921 0.736486 0.993873 0.066 Uiso 1 1 calc R U . . .
C00L C 0.5218(4) 0.43302(13) 1.1654(3) 0.0489(5) Uani 1 1 d . . . . .
H00M H 0.530121 0.404418 1.258790 0.059 Uiso 1 1 calc R U . . .
C00M C 0.9251(4) 0.61495(13) 1.1144(3) 0.0472(5) Uani 1 1 d . . . . .
H00N H 1.047033 0.584711 1.146276 0.057 Uiso 1 1 calc R U . . .
C1 C 0.3248(4) 0.45035(15) 1.0896(4) 0.0625(7) Uani 1 1 d . . . . .
H1A H 0.306635 0.478868 0.995548 0.075 Uiso 1 1 calc R U . . .
H1B H 0.202013 0.434239 1.129435 0.075 Uiso 1 1 calc R U . . .
C00O C 0.9354(5) 0.68825(15) 1.1618(3) 0.0589(6) Uani 1 1 d . . . . .
H00O H 1.064450 0.706793 1.224575 0.071 Uiso 1 1 calc R U . . .
C00P C 1.0605(5) 0.26693(15) 0.2564(3) 0.0611(6) Uani 1 1 d . . . . .
H00P H 1.195195 0.292998 0.254215 0.092 Uiso 1 1 calc R U . . .
H00Q H 1.092758 0.215974 0.278423 0.092 Uiso 1 1 calc R U . . .
H00R H 0.963310 0.271784 0.152571 0.092 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
S001 C00F 1.771(2) . ?
S001 C006 1.7753(18) . ?
N002 C00B 1.362(2) . ?
N002 C006 1.418(2) . ?
N002 C00I 1.450(3) . ?
O003 C00B 1.353(3) . ?
O003 C00H 1.443(3) . ?
O004 C00B 1.200(3) . ?
C2 C006 1.337(2) . ?
C2 C008 1.495(2) . ?
C2 C00G 1.513(3) . ?
C007 C00F 1.387(3) . ?
C007 C00D 1.392(3) . ?
C007 H007 0.9300 . ?
C008 C00A 1.392(3) . ?
C008 C00M 1.395(3) . ?
C009 C00E 1.384(3) . ?
C009 C00D 1.391(3) . ?
C009 C00P 1.510(3) . ?
C00A C00K 1.387(3) . ?
C00A H00A 0.9300 . ?
C00C C00E 1.386(3) . ?
C00C C00F 1.399(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00G C00L 1.498(3) . ?
C00G H00B 0.9700 . ?
C00G H00F 0.9700 . ?
C00H C00I 1.518(4) . ?
C00H H00G 0.9700 . ?
C00H H00H 0.9700 . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00J C00O 1.368(4) . ?
C00J C00K 1.376(4) . ?
C00J H00K 0.9300 . ?
C00K H00L 0.9300 . ?
C00L C1 1.299(4) . ?
C00L H00M 0.9300 . ?
C00M C00O 1.391(3) . ?
C00M H00N 0.9300 . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9600 . ?
C00P H00Q 0.9600 . ?
C00P H00R 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
C00F S001 C006 106.20(9) . . ?
C00B N002 C006 122.67(16) . . ?
C00B N002 C00I 112.54(17) . . ?
C006 N002 C00I 123.96(16) . . ?
C00B O003 C00H 109.69(17) . . ?
C006 C2 C008 122.24(16) . . ?
C006 C2 C00G 121.36(17) . . ?
C008 C2 C00G 116.33(15) . . ?
C2 C006 N002 122.48(16) . . ?
C2 C006 S001 119.68(14) . . ?
N002 C006 S001 117.54(13) . . ?
C00F C007 C00D 119.50(19) . . ?
C00F C007 H007 120.3 . . ?
C00D C007 H007 120.3 . . ?
C00A C008 C00M 118.25(19) . . ?
C00A C008 C2 121.32(16) . . ?
C00M C008 C2 120.31(18) . . ?
C00E C009 C00D 117.90(19) . . ?
C00E C009 C00P 120.9(2) . . ?
C00D C009 C00P 121.2(2) . . ?
C00K C00A C008 120.5(2) . . ?
C00K C00A H00A 119.7 . . ?
C008 C00A H00A 119.7 . . ?
O004 C00B O003 122.27(19) . . ?
O004 C00B N002 128.72(19) . . ?
O003 C00B N002 109.00(18) . . ?
C00E C00C C00F 120.01(19) . . ?
C00E C00C H00C 120.0 . . ?
C00F C00C H00C 120.0 . . ?
C009 C00D C007 121.8(2) . . ?
C009 C00D H00D 119.1 . . ?
C007 C00D H00D 119.1 . . ?
C009 C00E C00C 121.43(19) . . ?
C009 C00E H00E 119.3 . . ?
C00C C00E H00E 119.3 . . ?
C007 C00F C00C 119.33(18) . . ?
C007 C00F S001 125.06(15) . . ?
C00C C00F S001 115.53(15) . . ?
C00L C00G C2 114.68(16) . . ?
C00L C00G H00B 108.6 . . ?
C2 C00G H00B 108.6 . . ?
C00L C00G H00F 108.6 . . ?
C2 C00G H00F 108.6 . . ?
H00B C00G H00F 107.6 . . ?
O003 C00H C00I 105.80(18) . . ?
O003 C00H H00G 110.6 . . ?
C00I C00H H00G 110.6 . . ?
O003 C00H H00H 110.6 . . ?
C00I C00H H00H 110.6 . . ?
H00G C00H H00H 108.7 . . ?
N002 C00I C00H 100.73(19) . . ?
N002 C00I H00I 111.6 . . ?
C00H C00I H00I 111.6 . . ?
N002 C00I H00J 111.6 . . ?
C00H C00I H00J 111.6 . . ?
H00I C00I H00J 109.4 . . ?
C00O C00J C00K 120.0(2) . . ?
C00O C00J H00K 120.0 . . ?
C00K C00J H00K 120.0 . . ?
C00J C00K C00A 120.4(2) . . ?
C00J C00K H00L 119.8 . . ?
C00A C00K H00L 119.8 . . ?
C1 C00L C00G 127.4(2) . . ?
C1 C00L H00M 116.3 . . ?
C00G C00L H00M 116.3 . . ?
C00O C00M C008 120.5(2) . . ?
C00O C00M H00N 119.7 . . ?
C008 C00M H00N 119.7 . . ?
C00L C1 H1A 120.0 . . ?
C00L C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C00J C00O C00M 120.3(2) . . ?
C00J C00O H00O 119.8 . . ?
C00M C00O H00O 119.8 . . ?
C009 C00P H00P 109.5 . . ?
C009 C00P H00Q 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
C009 C00P H00R 109.5 . . ?
H00P C00P H00R 109.5 . . ?
H00Q C00P H00R 109.5 . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.028

