# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_L1-DMSO
_database_code_depnum_ccdc_archive 'CCDC 2501001'
loop_
_audit_author_name
_audit_author_address
'Patrizia Rossi'
;University of Firenze
Italy
;
_audit_update_record             
;
2025-12-06 deposited with the CCDC.	2025-12-26 downloaded from the CCDC.
;
_publ_section_title_             
;
Synthesis and Binding Studies of Two New 
Coumarin-Squaramide-Based Receptors for NSAIDs
;


_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            'C23 H19 F3 N2 O5 S'
_chemical_formula_weight         492.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   20.5435(5)
_cell_length_b                   7.9840(2)
_cell_length_c                   26.6642(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4373.44(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      67.87

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             2032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.904
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5167
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2016/2, Sheldrick 2015'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50298
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.315
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3977
_reflns_number_gt                3104
_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    'SIR-2004 (Burla, 2005)'
_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)+(0.0804P)²+2.1148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3977
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O 0.80458(8) 0.9071(2) 0.15113(6) 0.0298(4) Uani 1 1 d . . . . .
O2 O 0.84985(7) 0.6848(3) 0.24713(6) 0.0291(4) Uani 1 1 d . . . . .
O3 O 0.85210(7) 0.3866(2) 0.38111(6) 0.0233(4) Uani 1 1 d . . . . .
O4 O 0.93133(8) 0.2737(3) 0.42581(6) 0.0325(5) Uani 1 1 d . . . . .
N1 N 0.65159(10) 0.8438(3) 0.18124(8) 0.0262(5) Uani 1 1 d . . . . .
H1N H 0.6174(15) 0.800(4) 0.1959(11) 0.031 Uiso 1 1 d . U . . .
N2 N 0.68964(9) 0.6174(3) 0.27360(7) 0.0215(4) Uani 1 1 d . . . . .
H2N H 0.6483(14) 0.625(4) 0.2682(10) 0.026 Uiso 1 1 d . U . . .
C1 C 0.54258(12) 0.9614(4) 0.08342(9) 0.0272(6) Uani 1 1 d . . . . .
H1 H 0.5383(14) 1.079(4) 0.0920(11) 0.033 Uiso 1 1 d . U . . .
C2 C 0.49666(12) 0.8847(4) 0.05271(10) 0.0343(7) Uani 1 1 d . . . . .
H2 H 0.4619(15) 0.958(4) 0.0400(12) 0.041 Uiso 1 1 d . U . . .
C3 C 0.50280(14) 0.7181(5) 0.04035(10) 0.0412(8) Uani 1 1 d . . . . .
H3 H 0.4722(17) 0.668(5) 0.0205(13) 0.049 Uiso 1 1 d . U . . .
C4 C 0.55561(15) 0.6263(4) 0.05766(10) 0.0387(7) Uani 1 1 d . . . . .
H4 H 0.5581(16) 0.508(5) 0.0524(13) 0.046 Uiso 1 1 d . U . . .
C5 C 0.60187(13) 0.7017(4) 0.08779(9) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.6392(14) 0.639(4) 0.0987(12) 0.035 Uiso 1 1 d . U . . .
C6 C 0.59528(11) 0.8694(4) 0.10125(8) 0.0246(6) Uani 1 1 d . . . . .
C7 C 0.64392(12) 0.9489(4) 0.13674(10) 0.0282(6) Uani 1 1 d . . . . .
H7A H 0.6889(15) 0.958(4) 0.1220(11) 0.034 Uiso 1 1 d . U . . .
H7B H 0.6300(14) 1.061(4) 0.1460(11) 0.034 Uiso 1 1 d . U . . .
C8 C 0.70865(11) 0.7976(3) 0.19882(9) 0.0228(5) Uani 1 1 d . . . . .
C9 C 0.77705(11) 0.8298(3) 0.18436(9) 0.0229(5) Uani 1 1 d . . . . .
C10 C 0.79753(11) 0.7257(3) 0.22922(9) 0.0227(5) Uani 1 1 d . . . . .
C11 C 0.72814(11) 0.6983(3) 0.24006(8) 0.0210(5) Uani 1 1 d . . . . .
C12 C 0.70832(11) 0.5336(3) 0.31683(8) 0.0214(5) Uani 1 1 d . . . . .
C13 C 0.65887(11) 0.4804(3) 0.34977(9) 0.0233(5) Uani 1 1 d . . . . .
H13 H 0.6142(14) 0.513(4) 0.3421(10) 0.028 Uiso 1 1 d . U . . .
C14 C 0.67394(12) 0.3986(3) 0.39355(9) 0.0232(5) Uani 1 1 d . . . . .
H14 H 0.6391(13) 0.356(4) 0.4148(11) 0.028 Uiso 1 1 d . U . . .
C15 C 0.73919(11) 0.3649(3) 0.40653(8) 0.0219(5) Uani 1 1 d . . . . .
C16 C 0.78700(11) 0.4166(3) 0.37251(9) 0.0207(5) Uani 1 1 d . . . . .
C17 C 0.77305(11) 0.4991(3) 0.32810(8) 0.0216(5) Uani 1 1 d . . . . .
H17 H 0.8081(14) 0.540(4) 0.3080(10) 0.026 Uiso 1 1 d . U . . .
C18 C 0.76144(12) 0.2868(3) 0.45252(8) 0.0221(5) Uani 1 1 d . . . . .
C19 C 0.82502(12) 0.2568(3) 0.46034(9) 0.0254(5) Uani 1 1 d . . . . .
H19 H 0.8407(14) 0.202(4) 0.4888(11) 0.030 Uiso 1 1 d . U . . .
C20 C 0.87374(12) 0.3019(3) 0.42324(9) 0.0251(5) Uani 1 1 d . . . . .
C21 C 0.71272(12) 0.2433(3) 0.49264(9) 0.0277(6) Uani 1 1 d . . . . .
F1 F 0.66710(7) 0.1350(2) 0.47557(6) 0.0359(4) Uani 1 1 d . . . . .
F3 F 0.73990(8) 0.1722(2) 0.53263(6) 0.0430(4) Uani 1 1 d . . . . .
F2 F 0.68003(8) 0.3780(2) 0.50885(5) 0.0339(4) Uani 1 1 d . . . . .
S1D S 0.50316(3) 0.54241(8) 0.22436(2) 0.02289(18) Uani 1 1 d . . . . .
O1D O 0.56118(8) 0.6479(2) 0.24041(6) 0.0288(4) Uani 1 1 d . . . . .
C1D C 0.46213(12) 0.6665(4) 0.17863(10) 0.0254(6) Uani 1 1 d . . . . .
H1DA H 0.4922(15) 0.700(4) 0.1546(12) 0.038 Uiso 1 1 d . U . . .
H1DB H 0.4428(15) 0.759(4) 0.1939(12) 0.038 Uiso 1 1 d . U . . .
H1DC H 0.4275(15) 0.598(4) 0.1659(11) 0.038 Uiso 1 1 d . U . . .
C2D C 0.53404(13) 0.3847(4) 0.18287(10) 0.0296(6) Uani 1 1 d . . . . .
H2DA H 0.5602(16) 0.439(4) 0.1591(13) 0.044 Uiso 1 1 d . U . . .
H2DB H 0.5594(16) 0.302(5) 0.2023(12) 0.044 Uiso 1 1 d . U . . .
H2DC H 0.4964(16) 0.324(5) 0.1669(12) 0.044 Uiso 1 1 d . 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
O1 C9 1.219(3) . ?
O2 C10 1.220(3) . ?
O3 C16 1.378(3) . ?
O3 C20 1.384(3) . ?
O4 C20 1.206(3) . ?
N1 C8 1.315(3) . ?
N1 C7 1.462(3) . ?
N1 H1N 0.88(3) . ?
N2 C11 1.357(3) . ?
N2 C12 1.387(3) . ?
N2 H2N 0.86(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.392(4) . ?
C1 H1 0.97(3) . ?
C2 C3 1.376(5) . ?
C2 H2 0.98(3) . ?
C3 C4 1.388(5) . ?
C3 H3 0.91(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.95(4) . ?
C5 C6 1.393(4) . ?
C5 H5 0.96(3) . ?
C6 C7 1.516(3) . ?
C7 H7A 1.01(3) . ?
C7 H7B 0.97(3) . ?
C8 C11 1.413(3) . ?
C8 C9 1.479(3) . ?
C9 C10 1.516(3) . ?
C10 C11 1.471(3) . ?
C12 C17 1.391(3) . ?
C12 C13 1.409(3) . ?
C13 C14 1.373(4) . ?
C13 H13 0.98(3) . ?
C14 C15 1.410(3) . ?
C14 H14 0.98(3) . ?
C15 C16 1.399(3) . ?
C15 C18 1.450(3) . ?
C16 C17 1.385(3) . ?
C17 H17 0.95(3) . ?
C18 C19 1.344(3) . ?
C18 C21 1.505(3) . ?
C19 C20 1.453(3) . ?
C19 H19 0.93(3) . ?
C21 F3 1.331(3) . ?
C21 F2 1.339(3) . ?
C21 F1 1.354(3) . ?
S1D O1D 1.5210(18) . ?
S1D C1D 1.783(3) . ?
S1D C2D 1.792(3) . ?
C1D H1DA 0.93(3) . ?
C1D H1DB 0.93(3) . ?
C1D H1DC 0.96(3) . ?
C2D H2DA 0.94(4) . ?
C2D H2DB 0.99(4) . ?
C2D H2DC 1.01(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
C16 O3 C20 122.10(18) . . ?
C8 N1 C7 123.1(2) . . ?
C8 N1 H1N 116.4(19) . . ?
C7 N1 H1N 120.3(19) . . ?
C11 N2 C12 128.0(2) . . ?
C11 N2 H2N 115.4(19) . . ?
C12 N2 H2N 116.4(19) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 H1 120.2(18) . . ?
C6 C1 H1 120.0(18) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 123.9(19) . . ?
C1 C2 H2 116(2) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 120(2) . . ?
C4 C3 H3 120(2) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 119(2) . . ?
C3 C4 H4 121(2) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0(19) . . ?
C6 C5 H5 119.8(19) . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 120.0(2) . . ?
N1 C7 C6 109.7(2) . . ?
N1 C7 H7A 105.1(17) . . ?
C6 C7 H7A 113.1(17) . . ?
N1 C7 H7B 110.8(18) . . ?
C6 C7 H7B 110.5(18) . . ?
H7A C7 H7B 108(3) . . ?
N1 C8 C11 133.4(2) . . ?
N1 C8 C9 134.8(2) . . ?
C11 C8 C9 91.77(19) . . ?
O1 C9 C8 135.9(2) . . ?
O1 C9 C10 136.3(2) . . ?
C8 C9 C10 87.88(18) . . ?
O2 C10 C11 137.5(2) . . ?
O2 C10 C9 134.4(2) . . ?
C11 C10 C9 88.13(18) . . ?
N2 C11 C8 127.9(2) . . ?
N2 C11 C10 139.9(2) . . ?
C8 C11 C10 92.20(19) . . ?
N2 C12 C17 122.7(2) . . ?
N2 C12 C13 117.7(2) . . ?
C17 C12 C13 119.7(2) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 121.1(17) . . ?
C12 C13 H13 117.9(17) . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.7(16) . . ?
C15 C14 H14 119.2(16) . . ?
C16 C15 C14 116.9(2) . . ?
C16 C15 C18 117.0(2) . . ?
C14 C15 C18 126.1(2) . . ?
O3 C16 C17 115.2(2) . . ?
O3 C16 C15 121.5(2) . . ?
C17 C16 C15 123.3(2) . . ?
C16 C17 C12 118.5(2) . . ?
C16 C17 H17 119.0(17) . . ?
C12 C17 H17 122.3(17) . . ?
C19 C18 C15 120.9(2) . . ?
C19 C18 C21 119.7(2) . . ?
C15 C18 C21 119.4(2) . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 123.1(17) . . ?
C20 C19 H19 115.6(17) . . ?
O4 C20 O3 116.9(2) . . ?
O4 C20 C19 126.2(2) . . ?
O3 C20 C19 116.9(2) . . ?
F3 C21 F2 107.1(2) . . ?
F3 C21 F1 106.7(2) . . ?
F2 C21 F1 105.9(2) . . ?
F3 C21 C18 112.9(2) . . ?
F2 C21 C18 112.2(2) . . ?
F1 C21 C18 111.6(2) . . ?
O1D S1D C1D 104.78(12) . . ?
O1D S1D C2D 106.59(12) . . ?
C1D S1D C2D 97.80(13) . . ?
S1D C1D H1DA 108.5(19) . . ?
S1D C1D H1DB 110.0(19) . . ?
H1DA C1D H1DB 111(3) . . ?
S1D C1D H1DC 106.0(19) . . ?
H1DA C1D H1DC 114(3) . . ?
H1DB C1D H1DC 107(3) . . ?
S1D C2D H2DA 107(2) . . ?
S1D C2D H2DB 109.5(19) . . ?
H2DA C2D H2DB 111(3) . . ?
S1D C2D H2DC 109.0(19) . . ?
H2DA C2D H2DC 112(3) . . ?
H2DB C2D H2DC 108(3) . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.069

