# 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_3fb
_database_code_depnum_ccdc_archive 'CCDC 2154710'
loop_
_audit_author_name
_audit_author_address
'SATPAL SINGH BADSARA'
;University of Rajasthan
India
;
_audit_update_record             
;
2022-02-25 deposited with the CCDC.	2022-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
3-(Ethyl-3?-(4-methylphenylsulfonyl)-propanoate-2?-yl)-3-hydroxy-1-methylindolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O6 S'
_chemical_formula_sum            'C21 H23 N O6 S'
_chemical_formula_weight         417.46

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6303(7)
_cell_length_b                   10.9269(9)
_cell_length_c                   22.2548(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.664(3)
_cell_angle_gamma                90
_cell_volume                     2096.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7142
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      28.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31529
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         30.785
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6481
_reflns_number_gt                4649
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1258P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6481
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.2007
_refine_ls_wR_factor_gt          0.1613
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
C1 C 0.3298(3) 1.03264(19) 0.55277(12) 0.0593(6) Uani 1 1 d . . . . .
C2 C 0.2611(3) 1.04469(19) 0.49622(13) 0.0677(7) Uani 1 1 d . . . . .
H2 H 0.266111 1.119440 0.476425 0.081 Uiso 1 1 calc R U . . .
C3 C 0.1855(3) 0.94865(18) 0.46847(12) 0.0594(6) Uani 1 1 d . . . . .
H3 H 0.140564 0.957836 0.429939 0.071 Uiso 1 1 calc R U . . .
C4 C 0.1763(2) 0.83767(15) 0.49812(8) 0.0389(4) Uani 1 1 d . . . . .
C5 C 0.2441(3) 0.82231(19) 0.55448(9) 0.0587(6) Uani 1 1 d . . . . .
H5 H 0.237265 0.747612 0.574215 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3232(3) 0.9196(2) 0.58179(12) 0.0693(7) Uani 1 1 d . . . . .
H6 H 0.371986 0.909471 0.619601 0.083 Uiso 1 1 calc R U . . .
C7 C 0.4114(4) 1.1400(3) 0.58358(17) 0.0931(10) Uani 1 1 d . . . . .
H7A H 0.452140 1.193111 0.553808 0.140 Uiso 1 1 calc R U . . .
H7B H 0.494772 1.110411 0.609718 0.140 Uiso 1 1 calc R U . . .
H7C H 0.338950 1.184365 0.606732 0.140 Uiso 1 1 calc R U . . .
C8 C 0.24503(18) 0.61903(14) 0.44240(7) 0.0337(3) Uani 1 1 d . . . . .
H8A H 0.327404 0.670308 0.428143 0.040 Uiso 1 1 calc R U . . .
H8B H 0.284830 0.576382 0.478095 0.040 Uiso 1 1 calc R U . . .
C9 C 0.19769(16) 0.52555(14) 0.39385(7) 0.0291(3) Uani 1 1 d . . . . .
C10 C 0.20711(18) 0.58349(16) 0.33176(7) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.1255(3) 0.5642(3) 0.22894(9) 0.0706(7) Uani 1 1 d . . . . .
H11A H 0.232874 0.569546 0.218076 0.085 Uiso 1 1 calc R U . . .
H11B H 0.078392 0.644332 0.223745 0.085 Uiso 1 1 calc R U . . .
C12 C 0.0414(4) 0.4735(4) 0.19031(12) 0.0927(10) Uani 1 1 d . . . . .
H12A H 0.088880 0.394552 0.195772 0.139 Uiso 1 1 calc R U . . .
H12B H 0.045675 0.497620 0.148939 0.139 Uiso 1 1 calc R U . . .
H12C H -0.064821 0.469403 0.201150 0.139 Uiso 1 1 calc R U . . .
C13 C 0.30308(17) 0.40960(14) 0.39907(7) 0.0295(3) Uani 1 1 d . . . . .
C14 C 0.46596(17) 0.42938(14) 0.37977(7) 0.0312(3) Uani 1 1 d . . . . .
C15 C 0.58361(18) 0.50299(15) 0.40336(9) 0.0387(4) Uani 1 1 d . . . . .
H15 H 0.569086 0.550666 0.437257 0.046 Uiso 1 1 calc R U . . .
C16 C 0.7249(2) 0.50437(18) 0.37527(11) 0.0504(5) Uani 1 1 d . . . . .
H16 H 0.805133 0.554310 0.390122 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7461(2) 0.4315(2) 0.32527(10) 0.0538(5) Uani 1 1 d . . . . .
H17 H 0.841669 0.432280 0.307623 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6289(2) 0.3576(2) 0.30089(9) 0.0491(5) Uani 1 1 d . . . . .
H18 H 0.643125 0.310055 0.266937 0.059 Uiso 1 1 calc R U . . .
C19 C 0.48975(19) 0.35785(15) 0.32938(8) 0.0371(4) Uani 1 1 d . . . . .
C20 C 0.3429(3) 0.1986(3) 0.26587(13) 0.0765(8) Uani 1 1 d . . . . .
H20A H 0.387613 0.122550 0.279506 0.115 Uiso 1 1 calc R U . . .
H20B H 0.397081 0.227960 0.232032 0.115 Uiso 1 1 calc R U . . .
H20C H 0.235522 0.186315 0.254165 0.115 Uiso 1 1 calc R U . . .
C21 C 0.2426(2) 0.31008(16) 0.35379(9) 0.0406(4) Uani 1 1 d . . . . .
H9A H 0.088(2) 0.4984(16) 0.4005(8) 0.032(5) Uiso 1 1 d . . . . .
N1 N 0.35550(18) 0.28820(14) 0.31425(7) 0.0448(4) Uani 1 1 d . . . . .
O1 O 0.00690(18) 0.75283(15) 0.40665(8) 0.0606(4) Uani 1 1 d . . . . .
O2 O -0.00194(17) 0.64559(13) 0.50372(8) 0.0607(4) Uani 1 1 d . . . . .
O3 O 0.28848(19) 0.66770(16) 0.32012(7) 0.0608(4) Uani 1 1 d . . . . .
O4 O 0.11735(16) 0.52436(14) 0.29135(6) 0.0487(3) Uani 1 1 d . . . . .
O5 O 0.30423(15) 0.36246(11) 0.45848(5) 0.0395(3) Uani 1 1 d . . . . .
O6 O 0.11853(17) 0.25896(15) 0.35495(8) 0.0613(4) Uani 1 1 d . . . . .
S1 S 0.08609(5) 0.71255(4) 0.46126(2) 0.03826(15) Uani 1 1 d . . . . .
H5A H 0.213(3) 0.349(2) 0.4697(11) 0.054(6) 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
C1 C2 1.372(4) . ?
C1 C6 1.396(4) . ?
C1 C7 1.515(3) . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(3) . ?
C4 S1 1.7575(17) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.529(2) . ?
C8 S1 1.7764(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.526(2) . ?
C9 C13 1.561(2) . ?
C9 H9A 1.012(18) . ?
C10 O3 1.193(2) . ?
C10 O4 1.327(2) . ?
C11 O4 1.461(2) . ?
C11 C12 1.480(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O5 1.4185(19) . ?
C13 C14 1.504(2) . ?
C13 C21 1.556(2) . ?
C14 C15 1.380(2) . ?
C14 C19 1.390(2) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(2) . ?
C18 H18 0.9300 . ?
C19 N1 1.414(2) . ?
C20 N1 1.455(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O6 1.209(2) . ?
C21 N1 1.364(2) . ?
O1 S1 1.4356(16) . ?
O2 S1 1.4396(15) . ?
O5 H5A 0.85(3) . ?

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
C2 C1 C6 118.9(2) . . ?
C2 C1 C7 120.8(2) . . ?
C6 C1 C7 120.2(3) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.82(18) . . ?
C5 C4 S1 119.55(14) . . ?
C3 C4 S1 119.53(16) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 111.56(11) . . ?
C9 C8 H8A 109.3 . . ?
S1 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
S1 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 109.83(13) . . ?
C10 C9 C13 110.42(12) . . ?
C8 C9 C13 110.73(12) . . ?
C10 C9 H9A 110.2(11) . . ?
C8 C9 H9A 108.3(11) . . ?
C13 C9 H9A 107.3(10) . . ?
O3 C10 O4 124.00(16) . . ?
O3 C10 C9 124.98(15) . . ?
O4 C10 C9 110.96(14) . . ?
O4 C11 C12 108.0(2) . . ?
O4 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O4 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 C14 110.62(12) . . ?
O5 C13 C21 109.72(13) . . ?
C14 C13 C21 101.83(12) . . ?
O5 C13 C9 110.06(12) . . ?
C14 C13 C9 114.27(12) . . ?
C21 C13 C9 110.02(13) . . ?
C15 C14 C19 120.07(15) . . ?
C15 C14 C13 130.99(15) . . ?
C19 C14 C13 108.94(13) . . ?
C14 C15 C16 118.59(17) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 120.21(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 121.87(17) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 116.94(18) . . ?
C19 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?
C18 C19 C14 122.30(16) . . ?
C18 C19 N1 127.52(16) . . ?
C14 C19 N1 110.17(14) . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C21 N1 126.34(16) . . ?
O6 C21 C13 125.41(16) . . ?
N1 C21 C13 108.21(13) . . ?
C21 N1 C19 110.72(14) . . ?
C21 N1 C20 124.34(17) . . ?
C19 N1 C20 124.80(17) . . ?
C10 O4 C11 116.54(16) . . ?
C13 O5 H5A 111.8(16) . . ?
O1 S1 O2 117.81(10) . . ?
O1 S1 C4 109.87(9) . . ?
O2 S1 C4 108.96(9) . . ?
O1 S1 C8 108.58(9) . . ?
O2 S1 C8 107.44(9) . . ?
C4 S1 C8 103.15(8) . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.165

