# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_new7_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1946046'
loop_
_audit_author_name
_audit_author_address
'Sharvan Kumar'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2019-08-08 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'benzamide derivative'
_chemical_name_systematic        '4-(quinolin-2-ylcarbamoyl)phenyl acetate'
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31
_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'
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'

_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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
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                   9.5310(5)
_cell_length_b                   7.0315(4)
_cell_length_c                   21.6758(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.267(2)
_cell_angle_gamma                90
_cell_volume                     1450.29(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9023
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1292 before and 0.0454 after correction. The Ratio of minimum to maximum transmission is 0.9623. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       niddle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1525
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            62123
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         2.140
_diffrn_ambient_temperature      302.56
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3304
_reflns_number_total             3561
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.10(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+0.4398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1482
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C16(H16), C12(H12), C2(H2A), C13(H13), C3(H3), C15(H15), C7(H7),
 C6(H6), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O2 O 0.41642(12) 1.15185(16) 0.66304(4) 0.0467(3) Uani 1 1 d . . . . .
N2 N 0.24721(12) 0.45440(16) 0.48030(5) 0.0381(3) Uani 1 1 d . . . . .
H2 H 0.3042 0.5322 0.4641 0.046 Uiso 1 1 calc R . . . .
O1 O 0.11885(15) 0.40680(18) 0.56408(6) 0.0636(4) Uani 1 1 d . . . . .
O3 O 0.52274(16) 1.30483(18) 0.58773(5) 0.0638(4) Uani 1 1 d . . . . .
N1 N 0.21847(12) 0.31188(16) 0.38569(5) 0.0366(3) Uani 1 1 d . . . . .
C11 C 0.26420(14) 0.67908(18) 0.56552(5) 0.0347(3) Uani 1 1 d . . . . .
C16 C 0.39717(14) 0.7475(2) 0.55439(6) 0.0393(3) Uani 1 1 d . . . . .
H16 H 0.4508 0.6852 0.5261 0.047 Uiso 1 1 calc R . . . .
C1 C 0.20842(13) 0.29248(18) 0.44558(6) 0.0343(3) Uani 1 1 d . . . . .
C12 C 0.18353(14) 0.7753(2) 0.60706(6) 0.0378(3) Uani 1 1 d . . . . .
H12 H 0.0946 0.7302 0.6149 0.045 Uiso 1 1 calc R . . . .
C8 C 0.18961(13) 0.15689(19) 0.34904(6) 0.0361(3) Uani 1 1 d . . . . .
C2 C 0.16800(15) 0.1213(2) 0.47427(6) 0.0405(3) Uani 1 1 d . . . . .
H2A H 0.1628 0.1142 0.5169 0.049 Uiso 1 1 calc R . . . .
C10 C 0.20334(14) 0.50093(19) 0.53738(6) 0.0390(3) Uani 1 1 d . . . . .
C14 C 0.36862(14) 0.99977(19) 0.62618(6) 0.0366(3) Uani 1 1 d . . . . .
C13 C 0.23452(15) 0.9369(2) 0.63669(6) 0.0398(3) Uani 1 1 d . . . . .
H13 H 0.1793 1.0030 0.6635 0.048 Uiso 1 1 calc R . . . .
C3 C 0.13702(16) -0.0320(2) 0.43786(7) 0.0425(3) Uani 1 1 d . . . . .
H3 H 0.1092 -0.1453 0.4556 0.051 Uiso 1 1 calc R . . . .
C15 C 0.45125(14) 0.9073(2) 0.58486(6) 0.0405(3) Uani 1 1 d . . . . .
H15 H 0.5409 0.9515 0.5777 0.049 Uiso 1 1 calc R . . . .
C9 C 0.14693(14) -0.0199(2) 0.37306(6) 0.0384(3) Uani 1 1 d . . . . .
C17 C 0.49313(16) 1.2955(2) 0.64035(7) 0.0425(3) Uani 1 1 d . . . . .
C7 C 0.20040(16) 0.1747(2) 0.28438(7) 0.0479(4) Uani 1 1 d . . . . .
H7 H 0.2282 0.2897 0.2678 0.058 Uiso 1 1 calc R . . . .
C6 C 0.17006(18) 0.0231(3) 0.24629(7) 0.0562(4) Uani 1 1 d . . . . .
H6 H 0.1774 0.0361 0.2039 0.067 Uiso 1 1 calc R . . . .
C4 C 0.11692(18) -0.1740(2) 0.33251(8) 0.0518(4) Uani 1 1 d . . . . .
H4 H 0.0896 -0.2908 0.3481 0.062 Uiso 1 1 calc R . . . .
C18 C 0.5306(2) 1.4371(3) 0.68934(8) 0.0604(5) Uani 1 1 d . . . . .
H18A H 0.4502 1.5147 0.6964 0.091 Uiso 1 1 calc GR . . . .
H18B H 0.6058 1.5160 0.6765 0.091 Uiso 1 1 calc GR . . . .
H18C H 0.5600 1.3722 0.7268 0.091 Uiso 1 1 calc GR . . . .
C5 C 0.12816(19) -0.1507(3) 0.27037(8) 0.0579(5) Uani 1 1 d . . . . .
H5 H 0.1076 -0.2520 0.2438 0.069 Uiso 1 1 calc R . . . .


_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
O2 C14 1.3957(16) . ?
O2 C17 1.3556(17) . ?
N2 H2 0.8600 . ?
N2 C1 1.4027(16) . ?
N2 C10 1.3681(16) . ?
O1 C10 1.2144(17) . ?
O3 C17 1.1923(17) . ?
N1 C1 1.3142(16) . ?
N1 C8 1.3673(17) . ?
C11 C16 1.3895(18) . ?
C11 C12 1.3922(18) . ?
C11 C10 1.4958(18) . ?
C16 H16 0.9300 . ?
C16 C15 1.3877(19) . ?
C1 C2 1.4181(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.3802(19) . ?
C8 C9 1.4162(19) . ?
C8 C7 1.4167(18) . ?
C2 H2A 0.9300 . ?
C2 C3 1.3584(19) . ?
C14 C13 1.3834(19) . ?
C14 C15 1.3876(18) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C3 C9 1.4158(19) . ?
C15 H15 0.9300 . ?
C9 C4 1.4143(19) . ?
C17 C18 1.484(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.369(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C5 H5 0.9300 . ?

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
C17 O2 C14 121.90(10) . . ?
C1 N2 H2 116.8 . . ?
C10 N2 H2 116.8 . . ?
C10 N2 C1 126.48(11) . . ?
C1 N1 C8 117.88(11) . . ?
C16 C11 C12 119.13(12) . . ?
C16 C11 C10 123.74(12) . . ?
C12 C11 C10 117.07(12) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.03(12) . . ?
C15 C16 H16 119.5 . . ?
N2 C1 C2 121.57(11) . . ?
N1 C1 N2 114.44(11) . . ?
N1 C1 C2 123.93(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.55(12) . . ?
C13 C12 H12 119.7 . . ?
N1 C8 C9 122.58(12) . . ?
N1 C8 C7 118.75(12) . . ?
C9 C8 C7 118.66(12) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 C1 118.30(12) . . ?
C3 C2 H2A 120.8 . . ?
N2 C10 C11 115.96(11) . . ?
O1 C10 N2 123.08(13) . . ?
O1 C10 C11 120.95(12) . . ?
C13 C14 O2 115.14(11) . . ?
C13 C14 C15 121.35(12) . . ?
C15 C14 O2 123.35(12) . . ?
C12 C13 C14 119.37(12) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C9 120.28(12) . . ?
C9 C3 H3 119.9 . . ?
C16 C15 H15 120.7 . . ?
C14 C15 C16 118.52(12) . . ?
C14 C15 H15 120.7 . . ?
C3 C9 C8 117.01(12) . . ?
C4 C9 C8 119.76(13) . . ?
C4 C9 C3 123.22(13) . . ?
O2 C17 C18 110.67(12) . . ?
O3 C17 O2 123.36(13) . . ?
O3 C17 C18 125.96(14) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.23(15) . . ?
C6 C7 H7 119.9 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.73(15) . . ?
C5 C6 H6 119.6 . . ?
C9 C4 H4 120.1 . . ?
C5 C4 C9 119.74(15) . . ?
C5 C4 H4 120.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.88(15) . . ?
C4 C5 H5 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
