# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_t3tp_2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2345498'
loop_
_audit_author_name
_audit_author_address
'SUMY JOSEPH'
;NIRMALAGIRI COLLEGE, KANNUR UNIVERSITY
India
;
_audit_update_record             
;
2024-04-03 deposited with the CCDC.	2024-09-19 downloaded from the CCDC.
;
_audit_creation_date             2023-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O4 S'
_chemical_formula_sum            'C16 H16 O4 S'
_chemical_formula_weight         304.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   25.2752(12)
_cell_length_b                   4.1184(2)
_cell_length_c                   14.1008(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1467.80(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.072
_cell_measurement_theta_min      2.164
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1032 before and 0.0768 after correction. The Ratio of minimum to maximum transmission is 0.9164. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            101525
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.718
_diffrn_reflns_theta_min         2.164
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2673
_reflns_number_total             4540
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 
;
 Flack x determined using 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4540
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0863P)²+0.3480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.25148(5) 0.9929(4) 0.21291(14) 0.0688(4) Uani 1 1 d . . . . .
O1 O 0.49875(12) 0.6622(9) 0.8126(2) 0.0548(8) Uani 1 1 d . . . . .
O2 O 0.25565(16) 1.0235(13) 0.4184(3) 0.0888(17) Uani 1 1 d . . . . .
O3 O 0.40975(14) 0.9692(9) 0.8604(2) 0.0594(9) Uani 1 1 d . . . . .
O4 O 0.51713(13) 0.4672(9) 0.6351(2) 0.0612(9) Uani 1 1 d . . . . .
C1 C 0.2818(3) 0.8652(18) 0.1139(4) 0.0754(16) Uani 1 1 d . . . . .
H1 H 0.268559 0.898408 0.053178 0.090 Uiso 1 1 calc R . . . .
C2 C 0.30012(17) 0.8439(11) 0.2844(3) 0.0493(10) Uani 1 1 d . . . . .
C3 C 0.29551(17) 0.8943(14) 0.3857(3) 0.0551(11) Uani 1 1 d . . . . .
C4 C 0.33976(19) 0.7942(13) 0.4471(3) 0.0535(11) Uani 1 1 d . . . . .
H4 H 0.366846 0.668484 0.421761 0.064 Uiso 1 1 calc R . . . .
C5 C 0.34187(19) 0.8795(13) 0.5380(3) 0.0543(11) Uani 1 1 d . . . . .
H5 H 0.312994 0.996174 0.560601 0.065 Uiso 1 1 calc R . . . .
C6 C 0.38363(17) 0.8138(11) 0.6068(3) 0.0467(9) Uani 1 1 d . . . . .
C7 C 0.43086(18) 0.6585(12) 0.5832(3) 0.0494(10) Uani 1 1 d . . . . .
H7 H 0.436353 0.585715 0.521564 0.059 Uiso 1 1 calc R . . . .
C8 C 0.46935(17) 0.6128(12) 0.6509(3) 0.0476(9) Uani 1 1 d . . . . .
C9 C 0.46146(17) 0.7194(11) 0.7440(3) 0.0465(9) Uani 1 1 d . . . . .
C10 C 0.5404(2) 0.8901(14) 0.8149(4) 0.0698(14) Uani 1 1 d . . . . .
H10A H 0.556646 0.902326 0.753408 0.105 Uiso 1 1 calc GR . . . .
H10B H 0.566296 0.823417 0.860785 0.105 Uiso 1 1 calc GR . . . .
H10C H 0.526726 1.099423 0.831958 0.105 Uiso 1 1 calc GR . . . .
C11 C 0.34083(18) 0.6891(12) 0.2305(3) 0.0520(10) Uani 1 1 d . . . . .
H11 H 0.371019 0.591546 0.255220 0.062 Uiso 1 1 calc R . . . .
C12 C 0.3274(3) 0.7094(17) 0.1324(4) 0.0769(17) Uani 1 1 d . . . . .
H12 H 0.348504 0.621621 0.084837 0.092 Uiso 1 1 calc R . . . .
C13 C 0.37552(17) 0.9243(11) 0.6997(3) 0.0487(9) Uani 1 1 d . . . . .
H13 H 0.344324 1.030943 0.715582 0.058 Uiso 1 1 calc R . . . .
C14 C 0.41415(18) 0.8741(11) 0.7675(3) 0.0466(9) Uani 1 1 d . . . . .
C15 C 0.3616(2) 1.1244(14) 0.8875(4) 0.0643(13) Uani 1 1 d . . . . .
H15A H 0.355444 1.308511 0.847284 0.096 Uiso 1 1 calc GR . . . .
H15B H 0.364177 1.195040 0.952245 0.096 Uiso 1 1 calc GR . . . .
H15C H 0.332802 0.973884 0.881357 0.096 Uiso 1 1 calc GR . . . .
C16 C 0.5266(2) 0.3471(16) 0.5428(4) 0.0682(14) Uani 1 1 d . . . . .
H16A H 0.524518 0.522263 0.498027 0.102 Uiso 1 1 calc GR . . . .
H16B H 0.500600 0.185794 0.527433 0.102 Uiso 1 1 calc GR . . . .
H16C H 0.561269 0.251761 0.540205 0.102 Uiso 1 1 calc GR . . . .


_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 C1 1.676(7) . ?
S1 C2 1.704(5) . ?
O1 C9 1.372(5) . ?
O1 C10 1.411(6) . ?
O2 C3 1.229(6) . ?
O3 C14 1.371(5) . ?
O3 C15 1.427(6) . ?
O4 C8 1.367(5) . ?
O4 C16 1.413(6) . ?
C1 H1 0.9300 . ?
C1 C12 1.344(10) . ?
C2 C3 1.447(6) . ?
C2 C11 1.430(6) . ?
C3 C4 1.474(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.330(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.459(6) . ?
C6 C7 1.395(6) . ?
C6 C13 1.401(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(6) . ?
C8 C9 1.398(6) . ?
C9 C14 1.395(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.428(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.382(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 S1 C2 92.9(3) . . ?
C9 O1 C10 114.5(4) . . ?
C14 O3 C15 117.0(4) . . ?
C8 O4 C16 117.0(4) . . ?
S1 C1 H1 123.8 . . ?
C12 C1 S1 112.4(4) . . ?
C12 C1 H1 123.8 . . ?
C3 C2 S1 118.3(3) . . ?
C11 C2 S1 111.4(3) . . ?
C11 C2 C3 130.3(4) . . ?
O2 C3 C2 119.9(4) . . ?
O2 C3 C4 121.5(4) . . ?
C2 C3 C4 118.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 115.8 . . ?
C4 C5 C6 128.4(5) . . ?
C6 C5 H5 115.8 . . ?
C7 C6 C5 123.1(4) . . ?
C7 C6 C13 119.8(4) . . ?
C13 C6 C5 117.1(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
O4 C8 C7 124.9(4) . . ?
O4 C8 C9 114.6(4) . . ?
C7 C8 C9 120.5(4) . . ?
O1 C9 C8 120.7(4) . . ?
O1 C9 C14 120.0(4) . . ?
C14 C9 C8 119.3(4) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11 125.7 . . ?
C12 C11 C2 108.5(5) . . ?
C12 C11 H11 125.7 . . ?
C1 C12 C11 114.8(5) . . ?
C1 C12 H12 122.6 . . ?
C11 C12 H12 122.6 . . ?
C6 C13 H13 120.2 . . ?
C14 C13 C6 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
O3 C14 C9 115.3(4) . . ?
O3 C14 C13 124.1(4) . . ?
C13 C14 C9 120.6(4) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C12 C11 -0.9(7) . . . . ?
S1 C2 C3 O2 4.5(7) . . . . ?
S1 C2 C3 C4 -174.2(4) . . . . ?
S1 C2 C11 C12 0.0(5) . . . . ?
O1 C9 C14 O3 2.3(6) . . . . ?
O1 C9 C14 C13 -178.0(4) . . . . ?
O2 C3 C4 C5 -9.6(9) . . . . ?
O4 C8 C9 O1 -3.1(6) . . . . ?
O4 C8 C9 C14 179.5(4) . . . . ?
C1 S1 C2 C3 178.4(4) . . . . ?
C1 S1 C2 C11 -0.4(4) . . . . ?
C2 S1 C1 C12 0.7(5) . . . . ?
C2 C3 C4 C5 169.1(5) . . . . ?
C2 C11 C12 C1 0.6(7) . . . . ?
C3 C2 C11 C12 -178.6(5) . . . . ?
C3 C4 C5 C6 -177.0(5) . . . . ?
C4 C5 C6 C7 3.8(8) . . . . ?
C4 C5 C6 C13 -178.4(5) . . . . ?
C5 C6 C7 C8 178.0(5) . . . . ?
C5 C6 C13 C14 -178.9(4) . . . . ?
C6 C7 C8 O4 -179.3(4) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C6 C13 C14 O3 -179.2(4) . . . . ?
C6 C13 C14 C9 1.1(7) . . . . ?
C7 C6 C13 C14 -1.0(7) . . . . ?
C7 C8 C9 O1 177.2(4) . . . . ?
C7 C8 C9 C14 -0.2(7) . . . . ?
C8 C9 C14 O3 179.8(4) . . . . ?
C8 C9 C14 C13 -0.5(7) . . . . ?
C10 O1 C9 C8 83.5(6) . . . . ?
C10 O1 C9 C14 -99.1(5) . . . . ?
C11 C2 C3 O2 -177.0(5) . . . . ?
C11 C2 C3 C4 4.3(8) . . . . ?
C13 C6 C7 C8 0.2(7) . . . . ?
C15 O3 C14 C9 -179.2(4) . . . . ?
C15 O3 C14 C13 1.1(7) . . . . ?
C16 O4 C8 C7 -1.9(7) . . . . ?
C16 O4 C8 C9 178.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
