# 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_uo-14_auto
_database_code_depnum_ccdc_archive 'CCDC 2345449'
loop_
_audit_author_name
_audit_author_address
'Upendra Kumar Patel'
;Banaras Hindu University
India
;
_audit_update_record             
;
2024-04-02 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-04-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Prop-2-yn-1-yl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate'
_chemical_formula_moiety         'C15 H11 Cl F N O3'
_chemical_formula_sum            'C15 H11 Cl F N O3'
_chemical_formula_weight         307.70
_chemical_melting_point          438-440
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'
Cl Cl 0.3639 0.7018 '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'

_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.9992(2)
_cell_length_b                   9.55020(10)
_cell_length_c                   20.3352(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.1920(10)
_cell_angle_gamma                90
_cell_volume                     2866.96(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.561
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'transparent  white'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Rectangular Parallelepiped'
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15237
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.048
_diffrn_reflns_theta_min         4.418
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2419
_reflns_number_total             2804
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00073(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.115
_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)+(0.0894P)²+1.6723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1666
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00J(H00D,H00F)
1.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00G(H00G)
1.c Idealised Me refined as rotating group:
 C00L(H00H,H00I,H00J)
1.d :
 C00M(H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl01 Cl 0.75348(5) 0.40264(8) 0.36320(3) 0.0650(3) Uani 1 1 d . . . . .
F002 F 0.81314(9) 0.47098(17) 0.50409(8) 0.0633(4) Uani 1 1 d . . . . .
O003 O 0.42148(11) 0.2586(2) 0.67139(7) 0.0550(5) Uani 1 1 d . . . . .
O004 O 0.56866(12) 0.3990(2) 0.63853(8) 0.0568(5) Uani 1 1 d . . . . .
O005 O 0.30051(11) 0.2642(2) 0.58973(8) 0.0605(5) Uani 1 1 d . . . . .
N006 N 0.46275(12) 0.2749(2) 0.44740(8) 0.0421(4) Uani 1 1 d . . . . .
C00A C 0.55105(14) 0.3266(2) 0.46148(10) 0.0390(5) Uani 1 1 d . . . . .
C00C C 0.41436(14) 0.2646(2) 0.49688(10) 0.0400(5) Uani 1 1 d . . . . .
H00C H 0.355219 0.231726 0.486013 0.048 Uiso 1 1 calc R U . . .
C00D C 0.72596(14) 0.4260(2) 0.49041(12) 0.0449(5) Uani 1 1 d . . . . .
C00E C 0.67728(15) 0.4179(2) 0.54042(11) 0.0443(5) Uani 1 1 d . . . . .
H00E H 0.702759 0.446096 0.583429 0.053 Uiso 1 1 calc R U . . .
C00F C 0.38102(15) 0.2742(3) 0.60769(10) 0.0437(5) Uani 1 1 d . . . . .
C00G C 0.60265(15) 0.3398(2) 0.41048(11) 0.0445(5) Uani 1 1 d . . . . .
H00G H 0.577939 0.315222 0.366802 0.053 Uiso 1 1 calc R U . . .
C00H C 0.68925(16) 0.3888(2) 0.42554(12) 0.0467(5) Uani 1 1 d . . . . .
C00I C 0.42586(18) 0.2141(4) 0.38127(12) 0.0644(8) Uani 1 1 d . . . . .
H00A H 0.438938 0.276143 0.346408 0.077 Uiso 1 1 calc R U . . .
H00B H 0.360600 0.205394 0.376474 0.077 Uiso 1 1 calc R U . . .
C00J C 0.36175(19) 0.2301(4) 0.71850(12) 0.0697(9) Uani 1 1 d . . . . .
H00D H 0.310491 0.293604 0.710219 0.084 Uiso 1 1 calc R U . . .
H00F H 0.393916 0.246640 0.763564 0.084 Uiso 1 1 calc R U . . .
C00K C 0.3293(3) 0.0866(5) 0.71286(13) 0.1009(16) Uani 1 1 d . . . . .
C00L C 0.4668(2) 0.0717(4) 0.3734(2) 0.0995(14) Uani 1 1 d . . . . .
H00H H 0.443206 0.035237 0.329800 0.149 Uiso 1 1 calc R U . . .
H00I H 0.451763 0.009225 0.406780 0.149 Uiso 1 1 calc R U . . .
H00J H 0.531460 0.080173 0.378641 0.149 Uiso 1 1 calc R U . . .
C00M C 0.3027(6) -0.0264(8) 0.71000(19) 0.204(4) Uani 1 1 d . . . . .
H00M H 0.281200 -0.117958 0.707696 0.245 Uiso 1 1 calc R U . . .
C007 C 0.58778(14) 0.3666(2) 0.52689(10) 0.0375(5) Uani 1 1 d . . . . .
C008 C 0.53583(14) 0.3565(2) 0.58193(10) 0.0397(5) Uani 1 1 d . . . . .
C009 C 0.44611(14) 0.2992(2) 0.56219(9) 0.0382(5) Uani 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
Cl01 C00H 1.728(2) . ?
F002 C00D 1.358(3) . ?
O003 C00F 1.338(3) . ?
O003 C00J 1.449(3) . ?
O004 C008 1.237(3) . ?
O005 C00F 1.202(3) . ?
N006 C00A 1.395(3) . ?
N006 C00C 1.344(3) . ?
N006 C00I 1.479(3) . ?
C00A C00G 1.405(3) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.355(3) . ?
C00D C00H 1.383(3) . ?
C00E H00E 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.364(3) . ?
C00I H00A 0.9700 . ?
C00I H00B 0.9700 . ?
C00I C00L 1.513(5) . ?
C00J H00D 0.9700 . ?
C00J H00F 0.9700 . ?
C00J C00K 1.452(5) . ?
C00K C00M 1.149(7) . ?
C00L H00H 0.9600 . ?
C00L H00I 0.9600 . ?
C00L H00J 0.9600 . ?
C00M H00M 0.9300 . ?
C007 C00A 1.400(3) . ?
C007 C00E 1.410(3) . ?
C007 C008 1.476(3) . ?
C008 C009 1.443(3) . ?
C009 C00C 1.369(3) . ?
C009 C00F 1.478(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
C00F O003 C00J 115.69(18) . . ?
C00A N006 C00I 120.96(17) . . ?
C00C N006 C00A 119.40(17) . . ?
C00C N006 C00I 119.16(18) . . ?
N006 C00A C00G 120.47(18) . . ?
N006 C00A C007 119.43(18) . . ?
C007 C00A C00G 120.10(19) . . ?
N006 C00C H00C 117.7 . . ?
N006 C00C C009 124.55(19) . . ?
C009 C00C H00C 117.7 . . ?
F002 C00D C00H 118.9(2) . . ?
C00E C00D F002 119.4(2) . . ?
C00E C00D C00H 121.7(2) . . ?
C00D C00E H00E 120.2 . . ?
C00D C00E C007 119.6(2) . . ?
C007 C00E H00E 120.2 . . ?
O003 C00F C009 112.78(18) . . ?
O005 C00F O003 123.0(2) . . ?
O005 C00F C009 124.2(2) . . ?
C00A C00G H00G 120.3 . . ?
C00H C00G C00A 119.5(2) . . ?
C00H C00G H00G 120.3 . . ?
C00D C00H Cl01 120.06(18) . . ?
C00G C00H Cl01 119.61(18) . . ?
C00G C00H C00D 120.3(2) . . ?
N006 C00I H00A 109.5 . . ?
N006 C00I H00B 109.5 . . ?
N006 C00I C00L 110.8(3) . . ?
H00A C00I H00B 108.1 . . ?
C00L C00I H00A 109.5 . . ?
C00L C00I H00B 109.5 . . ?
O003 C00J H00D 109.4 . . ?
O003 C00J H00F 109.4 . . ?
O003 C00J C00K 111.3(3) . . ?
H00D C00J H00F 108.0 . . ?
C00K C00J H00D 109.4 . . ?
C00K C00J H00F 109.4 . . ?
C00M C00K C00J 178.1(4) . . ?
C00I C00L H00H 109.5 . . ?
C00I C00L H00I 109.5 . . ?
C00I C00L H00J 109.5 . . ?
H00H C00L H00I 109.5 . . ?
H00H C00L H00J 109.5 . . ?
H00I C00L H00J 109.5 . . ?
C00K C00M H00M 180.0 . . ?
C00A C007 C00E 118.78(19) . . ?
C00A C007 C008 122.08(18) . . ?
C00E C007 C008 119.15(18) . . ?
O004 C008 C007 120.49(19) . . ?
O004 C008 C009 125.55(19) . . ?
C009 C008 C007 113.93(17) . . ?
C00C C009 C00F 114.40(18) . . ?
C00C C009 C008 120.57(18) . . ?
C008 C009 C00F 125.02(18) . . ?

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
F002 C00D C00E C007 -177.8(2) . . . . ?
F002 C00D C00H Cl01 -1.0(3) . . . . ?
F002 C00D C00H C00G 178.3(2) . . . . ?
O004 C008 C009 C00C 175.3(2) . . . . ?
O004 C008 C009 C00F -3.9(4) . . . . ?
N006 C00A C00G C00H -179.1(2) . . . . ?
C00A N006 C00C C009 -1.4(3) . . . . ?
C00A N006 C00I C00L 73.3(3) . . . . ?
C00A C00G C00H Cl01 179.02(17) . . . . ?
C00A C00G C00H C00D -0.3(4) . . . . ?
C00A C007 C00E C00D -0.7(3) . . . . ?
C00A C007 C008 O004 -176.5(2) . . . . ?
C00A C007 C008 C009 1.5(3) . . . . ?
C00C N006 C00A C00G -179.3(2) . . . . ?
C00C N006 C00A C007 0.2(3) . . . . ?
C00C N006 C00I C00L -98.7(3) . . . . ?
C00C C009 C00F O003 156.9(2) . . . . ?
C00C C009 C00F O005 -20.8(3) . . . . ?
C00E C00D C00H Cl01 179.29(18) . . . . ?
C00E C00D C00H C00G -1.4(4) . . . . ?
C00E C007 C00A N006 179.62(19) . . . . ?
C00E C007 C00A C00G -0.9(3) . . . . ?
C00E C007 C008 O004 3.6(3) . . . . ?
C00E C007 C008 C009 -178.47(19) . . . . ?
C00F O003 C00J C00K 75.0(3) . . . . ?
C00F C009 C00C N006 -178.0(2) . . . . ?
C00H C00D C00E C007 1.9(4) . . . . ?
C00I N006 C00A C00G 8.7(3) . . . . ?
C00I N006 C00A C007 -171.8(2) . . . . ?
C00I N006 C00C C009 170.7(2) . . . . ?
C00J O003 C00F O005 -0.7(4) . . . . ?
C00J O003 C00F C009 -178.4(2) . . . . ?
C007 C00A C00G C00H 1.4(3) . . . . ?
C007 C008 C009 C00C -2.6(3) . . . . ?
C007 C008 C009 C00F 178.3(2) . . . . ?
C008 C007 C00A N006 -0.3(3) . . . . ?
C008 C007 C00A C00G 179.2(2) . . . . ?
C008 C007 C00E C00D 179.2(2) . . . . ?
C008 C009 C00C N006 2.7(4) . . . . ?
C008 C009 C00F O003 -23.9(3) . . . . ?
C008 C009 C00F O005 158.4(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.120 0.250 44.8 10.8 ?
2 0.000 0.120 0.750 44.8 10.8 ?
3 0.500 0.380 0.250 44.8 10.8 ?
4 0.500 0.620 0.750 44.8 10.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethylacetate'
