# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_mo_VA237_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2445252'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-04-20 deposited with the CCDC.	2025-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl N O3'
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.3216(10)
_cell_length_b                   17.174(2)
_cell_length_c                   12.5583(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.459(4)
_cell_angle_gamma                90
_cell_volume                     1552.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5466
_cell_measurement_theta_min      2.372
_cell_measurement_theta_max      27.881

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5686
_exptl_absorpt_correction_T_max  0.7457
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON C14 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15183
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3553
_reflns_number_gt                2302
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0498P)²+0.8558P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3553
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.6064(3) 0.36667(15) 0.88686(18) 0.0545(6) Uani 1 1 d . . . . .
C2 C 0.5850(4) 0.44568(15) 0.8931(2) 0.0608(6) Uani 1 1 d . . . . .
H2 H 0.627533 0.472185 0.957377 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4992(3) 0.48510(15) 0.80188(19) 0.0583(6) Uani 1 1 d . . . . .
H3 H 0.484198 0.538769 0.805214 0.070 Uiso 1 1 calc R U . . .
C4 C 0.4347(3) 0.44650(14) 0.70530(18) 0.0503(5) Uani 1 1 d . . . . .
C5 C 0.4617(4) 0.36639(15) 0.70209(19) 0.0589(6) Uani 1 1 d . . . . .
H5 H 0.421241 0.339474 0.637879 0.071 Uiso 1 1 calc R U . . .
C6 C 0.5475(4) 0.32624(15) 0.79261(19) 0.0603(6) Uani 1 1 d . . . . .
H6 H 0.565126 0.272701 0.789824 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3417(3) 0.49071(15) 0.61143(18) 0.0544(6) Uani 1 1 d . . . . .
H7 H 0.333141 0.544328 0.619681 0.065 Uiso 1 1 calc R U . . .
C8 C 0.2687(3) 0.46122(15) 0.51566(18) 0.0544(6) Uani 1 1 d . . . . .
H8 H 0.275459 0.407490 0.508056 0.065 Uiso 1 1 calc R U . . .
C9 C 0.1803(3) 0.50419(14) 0.42271(18) 0.0522(6) Uani 1 1 d . . . . .
C10 C 0.1059(3) 0.47913(14) 0.32123(18) 0.0529(6) Uani 1 1 d . . . . .
C11 C 0.0967(5) 0.39787(16) 0.2804(2) 0.0777(8) Uani 1 1 d . . . . .
H11A H -0.023962 0.388249 0.237942 0.117 Uiso 1 1 calc R U . . .
H11B H 0.118537 0.362474 0.340579 0.117 Uiso 1 1 calc R U . . .
H11C H 0.189609 0.390314 0.236417 0.117 Uiso 1 1 calc R U . . .
C12 C 0.0391(3) 0.54765(13) 0.26165(18) 0.0499(5) Uani 1 1 d . . . . .
C13 C 0.0748(3) 0.60995(14) 0.33273(18) 0.0526(6) Uani 1 1 d . . . . .
C14 C 0.0282(4) 0.68545(16) 0.3053(2) 0.0630(7) Uani 1 1 d . . . . .
H14 H 0.054084 0.725301 0.355977 0.076 Uiso 1 1 calc R U . . .
C15 C -0.0592(4) 0.70087(15) 0.1992(2) 0.0626(7) Uani 1 1 d . . . . .
C16 C -0.0936(3) 0.63815(15) 0.12735(19) 0.0572(6) Uani 1 1 d . . . . .
C17 C -0.0486(3) 0.56235(15) 0.15503(18) 0.0544(6) Uani 1 1 d . . . . .
H17 H -0.075396 0.522274 0.104815 0.065 Uiso 1 1 calc R U . . .
C18 C -0.1122(5) 0.78324(18) 0.1648(3) 0.0888(10) Uani 1 1 d . . . . .
H18A H -0.242623 0.785438 0.135388 0.133 Uiso 1 1 calc R U . . .
H18B H -0.042805 0.799503 0.110830 0.133 Uiso 1 1 calc R U . . .
H18C H -0.084963 0.817176 0.226429 0.133 Uiso 1 1 calc R U . . .
N1 N 0.6919(3) 0.32392(16) 0.98406(18) 0.0703(6) Uani 1 1 d . . . . .
O1 O 0.7339(4) 0.35980(15) 1.06873(16) 0.1014(8) Uani 1 1 d . . . . .
O2 O 0.7173(4) 0.25422(14) 0.97744(18) 0.0994(8) Uani 1 1 d . . . . .
O3 O 0.1629(2) 0.58414(10) 0.43296(12) 0.0585(4) Uani 1 1 d . . . . .
Cl1 Cl -0.20222(11) 0.65621(5) -0.00648(5) 0.0816(3) 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 C2 1.370(4) . ?
C1 C6 1.373(3) . ?
C1 N1 1.464(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.392(3) . ?
C4 C7 1.462(3) . ?
C5 C6 1.380(3) . ?
C7 C8 1.325(3) . ?
C8 C9 1.432(3) . ?
C9 C10 1.362(3) . ?
C9 O3 1.387(3) . ?
C10 C12 1.432(3) . ?
C10 C11 1.484(4) . ?
C12 C13 1.387(3) . ?
C12 C17 1.399(3) . ?
C13 C14 1.369(3) . ?
C13 O3 1.379(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.399(4) . ?
C15 C18 1.509(4) . ?
C16 C17 1.372(3) . ?
C16 Cl1 1.752(2) . ?
N1 O2 1.216(3) . ?
N1 O1 1.219(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
C2 C1 C6 121.9(2) . . ?
C2 C1 N1 119.0(2) . . ?
C6 C1 N1 119.0(2) . . ?
C1 C2 C3 118.6(2) . . ?
C2 C3 C4 121.5(2) . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C7 119.4(2) . . ?
C5 C4 C7 122.5(2) . . ?
C6 C5 C4 121.1(2) . . ?
C1 C6 C5 118.9(2) . . ?
C8 C7 C4 125.8(2) . . ?
C7 C8 C9 126.2(2) . . ?
C10 C9 O3 111.8(2) . . ?
C10 C9 C8 130.1(2) . . ?
O3 C9 C8 118.0(2) . . ?
C9 C10 C12 105.7(2) . . ?
C9 C10 C11 127.3(2) . . ?
C12 C10 C11 127.1(2) . . ?
C13 C12 C17 118.5(2) . . ?
C13 C12 C10 106.9(2) . . ?
C17 C12 C10 134.6(2) . . ?
C14 C13 O3 126.0(2) . . ?
C14 C13 C12 124.0(2) . . ?
O3 C13 C12 110.0(2) . . ?
C13 C14 C15 118.0(2) . . ?
C14 C15 C16 117.9(2) . . ?
C14 C15 C18 120.1(3) . . ?
C16 C15 C18 122.0(2) . . ?
C17 C16 C15 124.1(2) . . ?
C17 C16 Cl1 117.2(2) . . ?
C15 C16 Cl1 118.70(19) . . ?
C16 C17 C12 117.5(2) . . ?
O2 N1 O1 122.6(2) . . ?
O2 N1 C1 118.9(2) . . ?
O1 N1 C1 118.4(3) . . ?
C13 O3 C9 105.60(17) . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
