# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_nadeem_ma_sid_ccdc_DRARSHAD
_audit_block_doi                 10.5517/ccdc.csd.cc2fgxwq
_database_code_depnum_ccdc_archive 'CCDC 2248674'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4OB00040D 2024
loop_
_audit_author_name
_audit_author_address
'Muhammad Nadeem Arshad'
;King Abdulaziz University
Saudi Arabia
;
_audit_update_record             
;
2024-04-17 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
; 
2-Amino-benzoic acid 2-chloro-6-methyl-quinolin-3-ylmethyl ester
;
_chemical_name_common            
;
2-Amino-benzoic acid 2-chloro-6-methyl-quinolin-3-ylmethyl ester
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl N2 O2'
_chemical_formula_sum            'C18 H15 Cl N2 O2'
_chemical_formula_weight         326.77

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'
Cl Cl 0.1484 0.1585 '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                   9.5600(8)
_cell_length_b                   17.5287(18)
_cell_length_c                   9.6337(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.077(2)
_cell_angle_gamma                90
_cell_volume                     1589.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    948
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      26.9
_exptl_crystal_description       prismatic
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_min  0.7056
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_special_details           ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23986
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3243
_reflns_number_gt                1739
_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_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_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)+(0.0641P)²+3.2851P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3243
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2350
_refine_ls_wR_factor_gt          0.1909
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.8133(5) 0.2280(3) 0.7552(6) 0.0628(14) Uani 1 1 d . . . . .
C2 C 0.8678(5) 0.3026(3) 0.7471(5) 0.0565(12) Uani 1 1 d . . . . .
C3 C 0.9853(5) 0.3089(3) 0.6875(5) 0.0590(13) Uani 1 1 d . . . . .
H3 H 1.025341 0.356695 0.679793 0.071 Uiso 1 1 calc R U . . .
C4 C 1.0483(5) 0.2438(3) 0.6367(5) 0.0531(12) Uani 1 1 d . . . . .
C5 C 0.9831(5) 0.1731(3) 0.6481(5) 0.0519(11) Uani 1 1 d . . . . .
C6 C 1.0410(6) 0.1076(3) 0.5973(6) 0.0639(14) Uani 1 1 d . . . . .
H6 H 0.997901 0.060475 0.604065 0.077 Uiso 1 1 calc R U . . .
C7 C 1.1592(6) 0.1125(3) 0.5385(6) 0.0702(15) Uani 1 1 d . . . . .
H7 H 1.195333 0.068388 0.504165 0.084 Uiso 1 1 calc R U . . .
C8 C 1.2289(5) 0.1821(3) 0.5277(6) 0.0686(15) Uani 1 1 d . . . . .
C9 C 1.1724(5) 0.2466(3) 0.5761(6) 0.0659(14) Uani 1 1 d . . . . .
H9 H 1.216659 0.293311 0.568765 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7974(5) 0.3701(3) 0.8010(6) 0.0652(14) Uani 1 1 d . . . . .
H10A H 0.778445 0.359951 0.894919 0.078 Uiso 1 1 calc R U . . .
H10B H 0.858171 0.414614 0.804997 0.078 Uiso 1 1 calc R U . . .
C11 C 0.5724(5) 0.4296(3) 0.7528(5) 0.0522(12) Uani 1 1 d . . . . .
C12 C 0.4427(5) 0.4396(3) 0.6488(5) 0.0499(11) Uani 1 1 d . . . . .
C13 C 0.4288(5) 0.4053(3) 0.5163(5) 0.0567(12) Uani 1 1 d . . . . .
H13 H 0.502011 0.374516 0.496494 0.068 Uiso 1 1 calc R U . . .
C14 C 0.3111(6) 0.4155(3) 0.4148(6) 0.0691(15) Uani 1 1 d . . . . .
H14 H 0.303825 0.392163 0.327112 0.083 Uiso 1 1 calc R U . . .
C15 C 0.2041(6) 0.4611(3) 0.4458(6) 0.0732(16) Uani 1 1 d . . . . .
H15 H 0.123162 0.468363 0.377964 0.088 Uiso 1 1 calc R U . . .
C16 C 0.2134(6) 0.4961(3) 0.5738(6) 0.0704(15) Uani 1 1 d . . . . .
H16 H 0.139150 0.527130 0.590596 0.084 Uiso 1 1 calc R U . . .
C17 C 0.3313(5) 0.4866(3) 0.6796(5) 0.0556(12) Uani 1 1 d . . . . .
C18 C 1.3626(7) 0.1858(4) 0.4639(8) 0.102(2) Uani 1 1 d . . . . .
H18A H 1.386484 0.135521 0.436084 0.153 Uiso 1 1 calc R U . . .
H18B H 1.347045 0.218596 0.382894 0.153 Uiso 1 1 calc R U . . .
H18C H 1.439233 0.205557 0.532336 0.153 Uiso 1 1 calc R U . . .
N1 N 0.8652(4) 0.1655(2) 0.7095(5) 0.0629(11) Uani 1 1 d . . . . .
N2 N 0.3354(5) 0.5211(3) 0.8059(5) 0.0833(15) Uani 1 1 d . . . . .
H2A H 0.265217 0.548914 0.820545 0.100 Uiso 1 1 calc R U . . .
H2B H 0.408082 0.515313 0.871534 0.100 Uiso 1 1 calc R U . . .
O1 O 0.5982(4) 0.4578(2) 0.8694(4) 0.0709(11) Uani 1 1 d . . . . .
O2 O 0.6661(3) 0.3830(2) 0.7045(4) 0.0634(10) Uani 1 1 d . . . . .
Cl1 Cl 0.66565(18) 0.21591(10) 0.8374(2) 0.1020(7) 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
C1 N1 1.309(6) . ?
C1 C2 1.415(7) . ?
C1 Cl1 1.748(5) . ?
C2 C3 1.353(7) . ?
C2 C10 1.498(7) . ?
C3 C4 1.417(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(6) . ?
C4 C9 1.411(6) . ?
C5 N1 1.368(6) . ?
C5 C6 1.400(7) . ?
C6 C7 1.353(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(7) . ?
C8 C18 1.514(7) . ?
C9 H9 0.9300 . ?
C10 O2 1.443(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O1 1.212(5) . ?
C11 O2 1.354(5) . ?
C11 C12 1.462(6) . ?
C12 C13 1.396(6) . ?
C12 C17 1.417(6) . ?
C13 C14 1.367(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(7) . ?
C16 H16 0.9300 . ?
C17 N2 1.354(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
N1 C1 C2 126.1(4) . . ?
N1 C1 Cl1 115.8(4) . . ?
C2 C1 Cl1 118.1(4) . . ?
C3 C2 C1 116.1(5) . . ?
C3 C2 C10 122.7(5) . . ?
C1 C2 C10 121.3(4) . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C9 118.8(4) . . ?
C5 C4 C3 117.6(4) . . ?
C9 C4 C3 123.7(5) . . ?
N1 C5 C6 118.5(4) . . ?
N1 C5 C4 122.1(4) . . ?
C6 C5 C4 119.4(4) . . ?
C7 C6 C5 120.3(5) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.9(5) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 118.2(5) . . ?
C9 C8 C18 121.0(5) . . ?
C7 C8 C18 120.8(5) . . ?
C8 C9 C4 121.5(5) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
O2 C10 C2 107.1(4) . . ?
O2 C10 H10A 110.3 . . ?
C2 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C2 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
O1 C11 O2 121.6(4) . . ?
O1 C11 C12 126.6(4) . . ?
O2 C11 C12 111.7(4) . . ?
C13 C12 C17 119.1(4) . . ?
C13 C12 C11 120.5(4) . . ?
C17 C12 C11 120.3(4) . . ?
C14 C13 C12 122.2(5) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 118.2(5) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C16 C15 C14 121.7(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 121.5(5) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
N2 C17 C16 119.8(5) . . ?
N2 C17 C12 122.9(5) . . ?
C16 C17 C12 117.3(5) . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C5 117.0(4) . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 O2 C10 115.3(4) . . ?

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
N1 C1 C2 C3 -0.6(8) . . . . ?
Cl1 C1 C2 C3 177.6(4) . . . . ?
N1 C1 C2 C10 178.9(5) . . . . ?
Cl1 C1 C2 C10 -2.9(7) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C10 C2 C3 C4 -179.5(5) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C2 C3 C4 C9 -178.8(5) . . . . ?
C9 C4 C5 N1 178.0(5) . . . . ?
C3 C4 C5 N1 -1.9(7) . . . . ?
C9 C4 C5 C6 -1.0(7) . . . . ?
C3 C4 C5 C6 179.1(5) . . . . ?
N1 C5 C6 C7 -178.7(5) . . . . ?
C4 C5 C6 C7 0.4(8) . . . . ?
C5 C6 C7 C8 0.9(8) . . . . ?
C6 C7 C8 C9 -1.4(8) . . . . ?
C6 C7 C8 C18 178.8(6) . . . . ?
C7 C8 C9 C4 0.7(8) . . . . ?
C18 C8 C9 C4 -179.5(6) . . . . ?
C5 C4 C9 C8 0.5(8) . . . . ?
C3 C4 C9 C8 -179.6(5) . . . . ?
C3 C2 C10 O2 108.0(5) . . . . ?
C1 C2 C10 O2 -71.5(6) . . . . ?
O1 C11 C12 C13 178.1(5) . . . . ?
O2 C11 C12 C13 -2.1(6) . . . . ?
O1 C11 C12 C17 0.3(8) . . . . ?
O2 C11 C12 C17 -180.0(4) . . . . ?
C17 C12 C13 C14 0.1(7) . . . . ?
C11 C12 C13 C14 -177.8(5) . . . . ?
C12 C13 C14 C15 0.0(8) . . . . ?
C13 C14 C15 C16 0.3(9) . . . . ?
C14 C15 C16 C17 -0.7(9) . . . . ?
C15 C16 C17 N2 -178.8(5) . . . . ?
C15 C16 C17 C12 0.8(8) . . . . ?
C13 C12 C17 N2 179.1(5) . . . . ?
C11 C12 C17 N2 -3.0(7) . . . . ?
C13 C12 C17 C16 -0.5(7) . . . . ?
C11 C12 C17 C16 177.4(5) . . . . ?
C2 C1 N1 C5 -0.1(8) . . . . ?
Cl1 C1 N1 C5 -178.3(4) . . . . ?
C6 C5 N1 C1 -179.6(5) . . . . ?
C4 C5 N1 C1 1.4(7) . . . . ?
O1 C11 O2 C10 -0.3(7) . . . . ?
C12 C11 O2 C10 180.0(4) . . . . ?
C2 C10 O2 C11 164.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A N1 0.86 2.39 3.163(6) 150.6 2_656
N2 H2B O1 0.86 2.08 2.718(6) 130.2 .
N2 H2B O1 0.86 2.55 3.103(6) 122.9 3_667

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.071

