# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_va381_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 2480462'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-08-14 deposited with the CCDC.	2026-06-15 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         'C20 H16 Cl N3 O3'
_chemical_formula_sum            'C20 H16 Cl N3 O3'
_chemical_formula_weight         381.81

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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                   40.292(10)
_cell_length_b                   5.3016(13)
_cell_length_c                   16.500(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.446(7)
_cell_angle_gamma                90
_cell_volume                     3524.5(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      3.0335
_cell_measurement_theta_max      26.887

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7177
_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
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_number            53460
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_max         28.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4400
_reflns_number_gt                3353
_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       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0417P)²+4.1576P] 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         4400
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_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 0.46684(5) -0.1529(5) -0.06678(14) 0.0554(5) Uani 1 1 d . . . . .
H1 H 0.484467 -0.244509 -0.045040 0.066 Uiso 1 1 calc R U . . .
C2 C 0.47320(5) 0.0277(5) -0.12429(14) 0.0575(6) Uani 1 1 d . . . . .
H2 H 0.494739 0.059287 -0.141457 0.069 Uiso 1 1 calc R U . . .
C3 C 0.44663(5) 0.1612(4) -0.15587(13) 0.0494(5) Uani 1 1 d . . . . .
C4 C 0.41465(5) 0.1173(4) -0.13027(12) 0.0451(4) Uani 1 1 d . . . . .
H4 H 0.397292 0.211472 -0.152152 0.054 Uiso 1 1 calc R U . . .
C5 C 0.40797(4) -0.0656(4) -0.07223(11) 0.0394(4) Uani 1 1 d . . . . .
C6 C 0.43464(4) -0.2034(4) -0.03987(11) 0.0407(4) Uani 1 1 d . . . . .
C7 C 0.43121(5) -0.4033(4) 0.02106(11) 0.0433(4) Uani 1 1 d . . . . .
C8 C 0.41864(5) -0.6748(4) 0.10810(12) 0.0495(5) Uani 1 1 d . . . . .
C9 C 0.39880(7) -0.8244(5) 0.16525(15) 0.0681(7) Uani 1 1 d . . . . .
H9A H 0.381710 -0.913031 0.136081 0.102 Uiso 1 1 calc R U . . .
H9B H 0.388866 -0.714158 0.204323 0.102 Uiso 1 1 calc R U . . .
H9C H 0.412902 -0.943579 0.192613 0.102 Uiso 1 1 calc R U . . .
C10 C 0.37182(4) -0.1092(4) -0.05086(11) 0.0386(4) Uani 1 1 d . . . . .
H10 H 0.370834 -0.229487 -0.005858 0.046 Uiso 1 1 calc R U . . .
C11 C 0.35134(5) 0.1251(4) -0.02855(12) 0.0428(4) Uani 1 1 d . . . . .
H11A H 0.344739 0.118403 0.027819 0.051 Uiso 1 1 calc R U . . .
H11B H 0.364135 0.277653 -0.037158 0.051 Uiso 1 1 calc R U . . .
C12 C 0.32139(4) 0.1201(4) -0.08339(12) 0.0425(4) Uani 1 1 d . . . . .
C13 C 0.35303(4) -0.2197(3) -0.12308(12) 0.0392(4) Uani 1 1 d . . . . .
C14 C 0.29901(5) -0.1497(4) -0.19552(13) 0.0499(5) Uani 1 1 d . . . . .
H14A H 0.277453 -0.128039 -0.170687 0.060 Uiso 1 1 calc R U . . .
H14B H 0.301446 -0.327215 -0.208458 0.060 Uiso 1 1 calc R U . . .
C15 C 0.29953(4) -0.0015(4) -0.27328(12) 0.0412(4) Uani 1 1 d . . . . .
C16 C 0.32151(5) 0.1923(4) -0.28860(13) 0.0519(5) Uani 1 1 d . . . . .
H16 H 0.337624 0.233388 -0.250160 0.062 Uiso 1 1 calc R U . . .
C17 C 0.31982(6) 0.3258(5) -0.36044(14) 0.0612(6) Uani 1 1 d . . . . .
H17 H 0.334661 0.456882 -0.369663 0.073 Uiso 1 1 calc R U . . .
C18 C 0.29644(6) 0.2668(5) -0.41826(14) 0.0608(6) Uani 1 1 d . . . . .
H18 H 0.295245 0.358256 -0.466287 0.073 Uiso 1 1 calc R U . . .
C19 C 0.27480(5) 0.0713(5) -0.40464(14) 0.0612(6) Uani 1 1 d . . . . .
H19 H 0.259159 0.028235 -0.444004 0.073 Uiso 1 1 calc R U . . .
C20 C 0.27620(5) -0.0611(5) -0.33290(14) 0.0542(5) Uani 1 1 d . . . . .
H20 H 0.261330 -0.192354 -0.324164 0.065 Uiso 1 1 calc R U . . .
N1 N 0.44971(5) -0.7158(4) 0.09757(13) 0.0703(6) Uani 1 1 d . . . . .
N2 N 0.40595(4) -0.4808(3) 0.06209(10) 0.0483(4) Uani 1 1 d . . . . .
N3 N 0.32458(4) -0.0812(3) -0.13622(10) 0.0416(4) Uani 1 1 d . . . . .
O1 O 0.45861(4) -0.5331(4) 0.03879(10) 0.0693(5) Uani 1 1 d . . . . .
O2 O 0.29820(4) 0.2642(3) -0.08356(10) 0.0628(4) Uani 1 1 d . . . . .
O3 O 0.36113(4) -0.3998(3) -0.16294(10) 0.0541(4) Uani 1 1 d . . . . .
Cl1 Cl 0.45361(2) 0.38532(14) -0.23050(4) 0.0713(2) 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 1.374(3) . ?
C1 C6 1.400(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 Cl1 1.736(2) . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(2) . ?
C5 C10 1.519(2) . ?
C6 C7 1.468(3) . ?
C7 N2 1.293(3) . ?
C7 O1 1.332(2) . ?
C8 N1 1.284(3) . ?
C8 N2 1.375(3) . ?
C8 C9 1.473(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C13 1.524(3) . ?
C10 C11 1.537(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.503(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O2 1.207(2) . ?
C12 N3 1.385(3) . ?
C13 O3 1.206(2) . ?
C13 N3 1.377(2) . ?
C14 N3 1.461(2) . ?
C14 C15 1.505(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.381(3) . ?
C15 C20 1.392(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 O1 1.419(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 122.04(19) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C1 C2 C3 117.97(19) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 Cl1 119.32(16) . . ?
C2 C3 Cl1 119.24(17) . . ?
C3 C4 C5 120.99(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.28(17) . . ?
C4 C5 C10 117.19(16) . . ?
C6 C5 C10 124.48(17) . . ?
C1 C6 C5 119.28(19) . . ?
C1 C6 C7 116.59(17) . . ?
C5 C6 C7 124.13(17) . . ?
N2 C7 O1 112.03(18) . . ?
N2 C7 C6 131.79(17) . . ?
O1 C7 C6 116.17(17) . . ?
N1 C8 N2 114.2(2) . . ?
N1 C8 C9 122.0(2) . . ?
N2 C8 C9 123.7(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 C13 110.39(15) . . ?
C5 C10 C11 116.75(16) . . ?
C13 C10 C11 103.51(14) . . ?
C5 C10 H10 108.6 . . ?
C13 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
C12 C11 C10 105.75(15) . . ?
C12 C11 H11A 110.6 . . ?
C10 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
O2 C12 N3 124.19(18) . . ?
O2 C12 C11 127.47(19) . . ?
N3 C12 C11 108.34(15) . . ?
O3 C13 N3 124.40(18) . . ?
O3 C13 C10 126.58(17) . . ?
N3 C13 C10 109.02(15) . . ?
N3 C14 C15 115.25(16) . . ?
N3 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
N3 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C20 118.04(19) . . ?
C16 C15 C14 123.90(17) . . ?
C20 C15 C14 118.05(18) . . ?
C15 C16 C17 120.72(19) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.4(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C8 N1 O1 103.24(17) . . ?
C7 N2 C8 103.65(17) . . ?
C13 N3 C12 113.15(15) . . ?
C13 N3 C14 123.67(17) . . ?
C12 N3 C14 123.02(16) . . ?
C7 O1 N1 106.83(16) . . ?

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
C6 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 Cl1 -178.39(18) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
Cl1 C3 C4 C5 178.21(15) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C10 -177.09(18) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 179.3(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C10 C5 C6 C1 177.35(19) . . . . ?
C4 C5 C6 C7 -179.37(18) . . . . ?
C10 C5 C6 C7 -2.0(3) . . . . ?
C1 C6 C7 N2 173.8(2) . . . . ?
C5 C6 C7 N2 -6.8(3) . . . . ?
C1 C6 C7 O1 -6.3(3) . . . . ?
C5 C6 C7 O1 173.08(19) . . . . ?
C4 C5 C10 C13 66.5(2) . . . . ?
C6 C5 C10 C13 -110.8(2) . . . . ?
C4 C5 C10 C11 -51.3(2) . . . . ?
C6 C5 C10 C11 131.35(19) . . . . ?
C5 C10 C11 C12 126.21(17) . . . . ?
C13 C10 C11 C12 4.72(19) . . . . ?
C10 C11 C12 O2 176.6(2) . . . . ?
C10 C11 C12 N3 -3.9(2) . . . . ?
C5 C10 C13 O3 50.6(3) . . . . ?
C11 C10 C13 O3 176.26(19) . . . . ?
C5 C10 C13 N3 -129.81(16) . . . . ?
C11 C10 C13 N3 -4.14(19) . . . . ?
N3 C14 C15 C16 -2.1(3) . . . . ?
N3 C14 C15 C20 178.78(18) . . . . ?
C20 C15 C16 C17 1.3(3) . . . . ?
C14 C15 C16 C17 -177.8(2) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C16 C15 C20 C19 -0.8(3) . . . . ?
C14 C15 C20 C19 178.4(2) . . . . ?
N2 C8 N1 O1 -0.3(3) . . . . ?
C9 C8 N1 O1 -180.0(2) . . . . ?
O1 C7 N2 C8 -0.6(2) . . . . ?
C6 C7 N2 C8 179.3(2) . . . . ?
N1 C8 N2 C7 0.6(3) . . . . ?
C9 C8 N2 C7 -179.7(2) . . . . ?
O3 C13 N3 C12 -178.49(18) . . . . ?
C10 C13 N3 C12 1.9(2) . . . . ?
O3 C13 N3 C14 6.0(3) . . . . ?
C10 C13 N3 C14 -173.62(17) . . . . ?
O2 C12 N3 C13 -179.1(2) . . . . ?
C11 C12 N3 C13 1.3(2) . . . . ?
O2 C12 N3 C14 -3.6(3) . . . . ?
C11 C12 N3 C14 176.86(17) . . . . ?
C15 C14 N3 C13 -102.2(2) . . . . ?
C15 C14 N3 C12 82.7(2) . . . . ?
N2 C7 O1 N1 0.5(3) . . . . ?
C6 C7 O1 N1 -179.43(18) . . . . ?
C8 N1 O1 C7 -0.1(3) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.043

