# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ALD_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2152094'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto'
;Vellore Institute of Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 N2 O4 S'
_chemical_formula_sum            'C23 H24 N2 O4 S'
_chemical_formula_weight         424.50

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                   8.3812(7)
_cell_length_b                   9.8732(8)
_cell_length_c                   13.0649(11)
_cell_angle_alpha                82.404(3)
_cell_angle_beta                 88.395(3)
_cell_angle_gamma                86.109(3)
_cell_volume                     1068.96(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.50

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'φ and ω scans'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       'SADABS (BRUKER)'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39473
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.085
_diffrn_reflns_theta_max         28.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5322
_reflns_number_gt                3754
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0463P)²+0.4491P] 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         5322
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
S1_1 S -0.08635(5) 0.14255(5) 0.27448(4) 0.04755(15) Uani 1 1 d . . . . .
O1_1 O -0.14001(17) 0.28350(15) 0.24313(12) 0.0658(4) Uani 1 1 d . . . . .
O2_1 O 0.2662(3) 0.3084(3) 0.05233(15) 0.1178(8) Uani 1 1 d . . . . .
O3_1 O -0.15507(16) 0.08379(18) 0.37139(11) 0.0713(5) Uani 1 1 d . . . . .
O4_1 O -0.09606(17) 0.05738(15) 0.19348(11) 0.0624(4) Uani 1 1 d . . . . .
C1_1 C 0.1228(2) 0.14511(17) 0.29789(13) 0.0404(4) Uani 1 1 d . . . . .
C2_1 C 0.1778(2) 0.09406(19) 0.39526(14) 0.0449(4) Uani 1 1 d . . . . .
H2_1 H 0.106449 0.058493 0.446006 0.054 Uiso 1 1 calc R U . . .
C3_1 C 0.3376(2) 0.0955(2) 0.41762(16) 0.0529(5) Uani 1 1 d . . . . .
H3_1 H 0.373018 0.061152 0.483370 0.063 Uiso 1 1 calc R U . . .
C4_1 C 0.4446(2) 0.1473(2) 0.34359(18) 0.0599(5) Uani 1 1 d . . . . .
H4_1 H 0.552114 0.148278 0.359015 0.072 Uiso 1 1 calc R U . . .
C5_1 C 0.3915(2) 0.1976(2) 0.24648(17) 0.0584(5) Uani 1 1 d . . . . .
H5_1 H 0.464227 0.232494 0.196356 0.070 Uiso 1 1 calc R U . . .
C6_1 C 0.2306(2) 0.19748(19) 0.22164(14) 0.0469(4) Uani 1 1 d . . . . .
C7_1 C 0.1808(3) 0.2520(2) 0.11523(16) 0.0639(6) Uani 1 1 d . . . . .
H7_1 H 0.076460 0.241105 0.096948 0.077 Uiso 1 1 calc R U . . .
N1_2 N -0.01417(19) 0.67188(17) 0.26564(12) 0.0512(4) Uani 1 1 d . . . . .
N2_2 N 0.6859(2) 0.2381(2) 0.92073(14) 0.0650(5) Uani 1 1 d . . . . .
C1_2 C 0.1642(2) 0.58603(19) 0.44131(14) 0.0441(4) Uani 1 1 d . . . . .
C2_2 C 0.0875(3) 0.7162(2) 0.42291(17) 0.0582(5) Uani 1 1 d . . . . .
H2_2 H 0.095886 0.777159 0.470723 0.070 Uiso 1 1 calc R U . . .
C3_2 C 0.0003(3) 0.7563(2) 0.33640(17) 0.0613(5) Uani 1 1 d . . . . .
H3_2 H -0.049947 0.843818 0.326398 0.074 Uiso 1 1 calc R U . . .
C4_2 C 0.0547(3) 0.5447(2) 0.28160(16) 0.0576(5) Uani 1 1 d . . . . .
H4_2 H 0.041859 0.485114 0.233374 0.069 Uiso 1 1 calc R U . . .
C5_2 C 0.1431(3) 0.5006(2) 0.36683(15) 0.0548(5) Uani 1 1 d . . . . .
H5_2 H 0.190260 0.411923 0.375419 0.066 Uiso 1 1 calc R U . . .
C6_2 C 0.2542(2) 0.5465(2) 0.53486(15) 0.0491(4) Uani 1 1 d . . . . .
H6_2 H 0.258043 0.611209 0.580288 0.059 Uiso 1 1 calc R U . . .
C7_2 C 0.3320(2) 0.4251(2) 0.56114(15) 0.0498(4) Uani 1 1 d . . . . .
H7_2 H 0.327670 0.361768 0.514708 0.060 Uiso 1 1 calc R U . . .
C8_2 C 0.4227(2) 0.3805(2) 0.65388(14) 0.0476(4) Uani 1 1 d . . . . .
C9_2 C 0.4898(3) 0.2474(2) 0.67214(17) 0.0645(6) Uani 1 1 d . . . . .
H9_2 H 0.476302 0.188450 0.623561 0.077 Uiso 1 1 calc R U . . .
C10_2 C 0.5751(3) 0.1992(2) 0.75891(17) 0.0643(6) Uani 1 1 d . . . . .
H10_2 H 0.617593 0.109064 0.767776 0.077 Uiso 1 1 calc R U . . .
C11_2 C 0.5993(2) 0.2834(2) 0.83411(15) 0.0515(5) Uani 1 1 d . . . . .
C12_2 C 0.5326(2) 0.4187(2) 0.81591(16) 0.0545(5) Uani 1 1 d . . . . .
H12_2 H 0.546771 0.478248 0.863923 0.065 Uiso 1 1 calc R U . . .
C13_2 C 0.4470(2) 0.4646(2) 0.72885(15) 0.0517(5) Uani 1 1 d . . . . .
H13_2 H 0.403834 0.554614 0.719580 0.062 Uiso 1 1 calc R U . . .
C14_2 C -0.1061(3) 0.7177(3) 0.17099(17) 0.0702(6) Uani 1 1 d . . . . .
H14A_2 H -0.171211 0.646196 0.157079 0.105 Uiso 1 1 calc R U . . .
H14B_2 H -0.033492 0.738803 0.113837 0.105 Uiso 1 1 calc R U . . .
H14C_2 H -0.173218 0.797955 0.180585 0.105 Uiso 1 1 calc R U . . .
C15_2 C 0.6980(3) 0.3239(3) 1.00054(17) 0.0770(7) Uani 1 1 d . . . . .
H15A_2 H 0.756206 0.273958 1.057264 0.115 Uiso 1 1 calc R U . . .
H15B_2 H 0.592706 0.351633 1.023981 0.115 Uiso 1 1 calc R U . . .
H15C_2 H 0.753143 0.403519 0.973667 0.115 Uiso 1 1 calc R U . . .
C16_2 C 0.7343(4) 0.0936(3) 0.9447(2) 0.0845(8) Uani 1 1 d . . . . .
H16A_2 H 0.790379 0.078586 1.008716 0.127 Uiso 1 1 calc R U . . .
H16B_2 H 0.803314 0.065459 0.890451 0.127 Uiso 1 1 calc R U . . .
H16C_2 H 0.641293 0.041290 0.950841 0.127 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_1 O1_1 1.4427(15) . ?
S1_1 O3_1 1.4429(15) . ?
S1_1 O4_1 1.4432(15) . ?
S1_1 C1_1 1.7901(17) . ?
O2_1 C7_1 1.182(3) . ?
C1_1 C2_1 1.384(2) . ?
C1_1 C6_1 1.398(3) . ?
C2_1 C3_1 1.380(2) . ?
C3_1 C4_1 1.373(3) . ?
C4_1 C5_1 1.375(3) . ?
C5_1 C6_1 1.396(3) . ?
C6_1 C7_1 1.483(3) . ?
N1_2 C3_2 1.337(3) . ?
N1_2 C4_2 1.339(3) . ?
N1_2 C14_2 1.478(2) . ?
N2_2 C11_2 1.370(2) . ?
N2_2 C15_2 1.438(3) . ?
N2_2 C16_2 1.452(3) . ?
C1_2 C5_2 1.391(3) . ?
C1_2 C2_2 1.392(3) . ?
C1_2 C6_2 1.449(3) . ?
C2_2 C3_2 1.363(3) . ?
C4_2 C5_2 1.361(3) . ?
C6_2 C7_2 1.334(3) . ?
C7_2 C8_2 1.451(3) . ?
C8_2 C9_2 1.387(3) . ?
C8_2 C13_2 1.393(3) . ?
C9_2 C10_2 1.371(3) . ?
C10_2 C11_2 1.395(3) . ?
C11_2 C12_2 1.406(3) . ?
C12_2 C13_2 1.371(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
O1_1 S1_1 O3_1 114.06(10) . . ?
O1_1 S1_1 O4_1 113.11(9) . . ?
O3_1 S1_1 O4_1 113.02(10) . . ?
O1_1 S1_1 C1_1 105.33(9) . . ?
O3_1 S1_1 C1_1 105.01(8) . . ?
O4_1 S1_1 C1_1 105.21(8) . . ?
C2_1 C1_1 C6_1 119.52(16) . . ?
C2_1 C1_1 S1_1 118.31(14) . . ?
C6_1 C1_1 S1_1 122.16(13) . . ?
C3_1 C2_1 C1_1 120.53(18) . . ?
C4_1 C3_1 C2_1 120.53(18) . . ?
C3_1 C4_1 C5_1 119.47(18) . . ?
C4_1 C5_1 C6_1 121.26(19) . . ?
C5_1 C6_1 C1_1 118.68(17) . . ?
C5_1 C6_1 C7_1 118.78(19) . . ?
C1_1 C6_1 C7_1 122.53(18) . . ?
O2_1 C7_1 C6_1 123.8(2) . . ?
C3_2 N1_2 C4_2 119.31(17) . . ?
C3_2 N1_2 C14_2 120.53(18) . . ?
C4_2 N1_2 C14_2 120.15(18) . . ?
C11_2 N2_2 C15_2 120.63(18) . . ?
C11_2 N2_2 C16_2 119.90(19) . . ?
C15_2 N2_2 C16_2 117.89(18) . . ?
C5_2 C1_2 C2_2 115.53(17) . . ?
C5_2 C1_2 C6_2 124.60(17) . . ?
C2_2 C1_2 C6_2 119.85(17) . . ?
C3_2 C2_2 C1_2 121.46(19) . . ?
N1_2 C3_2 C2_2 121.08(19) . . ?
N1_2 C4_2 C5_2 121.48(19) . . ?
C4_2 C5_2 C1_2 121.11(19) . . ?
C7_2 C6_2 C1_2 125.36(19) . . ?
C6_2 C7_2 C8_2 127.42(19) . . ?
C9_2 C8_2 C13_2 116.34(17) . . ?
C9_2 C8_2 C7_2 120.14(18) . . ?
C13_2 C8_2 C7_2 123.52(18) . . ?
C10_2 C9_2 C8_2 122.7(2) . . ?
C9_2 C10_2 C11_2 121.05(19) . . ?
N2_2 C11_2 C10_2 122.09(18) . . ?
N2_2 C11_2 C12_2 121.22(19) . . ?
C10_2 C11_2 C12_2 116.68(17) . . ?
C13_2 C12_2 C11_2 121.37(19) . . ?
C12_2 C13_2 C8_2 121.91(18) . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.039

