# 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_KB1285_0m
_database_code_depnum_ccdc_archive 'CCDC 2371440'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 O4'
_chemical_formula_sum            'C19 H12 O4'
_chemical_formula_weight         304.29

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'
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                   6.4750(3)
_cell_length_b                   8.0563(4)
_cell_length_c                   27.3771(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.317(3)
_cell_angle_gamma                90
_cell_volume                     1426.95(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5308
_cell_measurement_theta_min      2.9785
_cell_measurement_theta_max      27.467

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6828
_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                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15912
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.636
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_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             3541
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0476P)²+0.4094P] 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         3541
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.2953(3) 0.6138(3) 0.53216(6) 0.0640(5) Uani 1 1 d . . . . .
H1 H 0.421714 0.560093 0.530009 0.077 Uiso 1 1 calc R U . . .
C2 C 0.1962(4) 0.6748(3) 0.49058(7) 0.0767(6) Uani 1 1 d . . . . .
H2 H 0.254610 0.661587 0.460340 0.092 Uiso 1 1 calc R U . . .
C3 C 0.0103(4) 0.7553(3) 0.49403(7) 0.0809(7) Uani 1 1 d . . . . .
H3 H -0.056166 0.796845 0.465864 0.097 Uiso 1 1 calc R U . . .
C4 C -0.0791(3) 0.7756(3) 0.53820(7) 0.0708(6) Uani 1 1 d . . . . .
H4 H -0.205074 0.830266 0.540070 0.085 Uiso 1 1 calc R U . . .
C5 C 0.0209(3) 0.7137(2) 0.57989(6) 0.0494(4) Uani 1 1 d . . . . .
C6 C 0.2076(3) 0.6320(2) 0.57752(6) 0.0468(4) Uani 1 1 d . . . . .
C7 C 0.3006(2) 0.5726(2) 0.62290(6) 0.0411(4) Uani 1 1 d . . . . .
C8 C 0.2134(2) 0.59252(19) 0.66685(5) 0.0373(3) Uani 1 1 d . . . . .
C9 C 0.0177(2) 0.6836(2) 0.66784(6) 0.0421(4) Uani 1 1 d . . . . .
C10 C 0.6007(2) 0.4360(2) 0.65821(6) 0.0455(4) Uani 1 1 d . . . . .
C11 C 0.5103(2) 0.4575(2) 0.70442(6) 0.0444(4) Uani 1 1 d . . . . .
H11 H 0.583158 0.418995 0.732118 0.053 Uiso 1 1 calc R U . . .
C12 C 0.3246(2) 0.5307(2) 0.71036(5) 0.0378(3) Uani 1 1 d . . . . .
C13 C 0.2484(2) 0.54133(19) 0.76077(5) 0.0382(3) Uani 1 1 d . . . . .
C14 C 0.0575(2) 0.4781(2) 0.77293(6) 0.0452(4) Uani 1 1 d . . . . .
H14 H -0.030339 0.433618 0.748609 0.054 Uiso 1 1 calc R U . . .
C15 C -0.0030(2) 0.4806(2) 0.82046(6) 0.0511(4) Uani 1 1 d . . . . .
H15 H -0.130446 0.435803 0.827836 0.061 Uiso 1 1 calc R U . . .
C16 C 0.1219(3) 0.5484(2) 0.85769(6) 0.0499(4) Uani 1 1 d . . . . .
C17 C 0.0503(3) 0.5548(3) 0.90950(7) 0.0735(6) Uani 1 1 d . . . . .
H17A H -0.096625 0.538736 0.909359 0.110 Uiso 1 1 calc R U . . .
H17B H 0.084404 0.660905 0.923593 0.110 Uiso 1 1 calc R U . . .
H17C H 0.117644 0.468779 0.928472 0.110 Uiso 1 1 calc R U . . .
C18 C 0.3136(3) 0.6107(2) 0.84563(6) 0.0494(4) Uani 1 1 d . . . . .
H18 H 0.400691 0.656112 0.869954 0.059 Uiso 1 1 calc R U . . .
C19 C 0.3765(2) 0.6059(2) 0.79801(6) 0.0436(4) Uani 1 1 d . . . . .
H19 H 0.506198 0.646475 0.790802 0.052 Uiso 1 1 calc R U . . .
O1 O -0.07047(17) 0.73710(16) 0.62364(4) 0.0524(3) Uani 1 1 d . . . . .
O2 O -0.07715(17) 0.71802(16) 0.70315(4) 0.0550(3) Uani 1 1 d . . . . .
O3 O 0.48459(16) 0.49652(15) 0.61778(4) 0.0503(3) Uani 1 1 d . . . . .
O4 O 0.76270(17) 0.37181(17) 0.64914(4) 0.0600(4) 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 1.394(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 O1 1.3701(19) . ?
C5 C6 1.381(2) . ?
C6 C7 1.440(2) . ?
C7 O3 1.3521(17) . ?
C7 C8 1.359(2) . ?
C8 C12 1.455(2) . ?
C8 C9 1.466(2) . ?
C9 O2 1.1985(17) . ?
C9 O1 1.3856(18) . ?
C10 O4 1.2046(18) . ?
C10 O3 1.4001(19) . ?
C10 C11 1.426(2) . ?
C11 C12 1.355(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.487(2) . ?
C13 C19 1.389(2) . ?
C13 C14 1.390(2) . ?
C14 C15 1.374(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9300 . ?
C16 C18 1.391(2) . ?
C16 C17 1.511(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.382(2) . ?
C18 H18 0.9300 . ?
C19 H19 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
C2 C1 C6 120.47(19) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 119.51(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.28(19) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.99(19) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
O1 C5 C6 121.09(14) . . ?
O1 C5 C4 117.90(16) . . ?
C6 C5 C4 121.00(16) . . ?
C5 C6 C1 118.75(16) . . ?
C5 C6 C7 117.02(14) . . ?
C1 C6 C7 124.23(16) . . ?
O3 C7 C8 122.99(14) . . ?
O3 C7 C6 113.62(13) . . ?
C8 C7 C6 123.39(14) . . ?
C7 C8 C12 118.36(13) . . ?
C7 C8 C9 117.77(14) . . ?
C12 C8 C9 123.78(13) . . ?
O2 C9 O1 115.21(14) . . ?
O2 C9 C8 127.04(14) . . ?
O1 C9 C8 117.75(13) . . ?
O4 C10 O3 115.52(14) . . ?
O4 C10 C11 128.83(15) . . ?
O3 C10 C11 115.65(13) . . ?
C12 C11 C10 123.88(14) . . ?
C12 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C11 C12 C8 117.58(13) . . ?
C11 C12 C13 117.77(13) . . ?
C8 C12 C13 124.65(13) . . ?
C19 C13 C14 118.14(14) . . ?
C19 C13 C12 119.49(13) . . ?
C14 C13 C12 122.22(13) . . ?
C15 C14 C13 120.80(15) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.39(15) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C18 117.86(15) . . ?
C15 C16 C17 120.73(16) . . ?
C18 C16 C17 121.41(17) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C16 120.89(15) . . ?
C19 C18 H18 119.6 . . ?
C16 C18 H18 119.6 . . ?
C18 C19 C13 120.88(14) . . ?
C18 C19 H19 119.6 . . ?
C13 C19 H19 119.6 . . ?
C5 O1 C9 122.92(12) . . ?
C7 O3 C10 121.53(12) . . ?

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 0.5(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 O1 179.3(2) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
O1 C5 C6 C1 -179.03(17) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
O1 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C6 C7 179.71(18) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C7 -179.84(19) . . . . ?
C5 C6 C7 O3 -178.94(15) . . . . ?
C1 C6 C7 O3 0.3(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C1 C6 C7 C8 179.52(17) . . . . ?
O3 C7 C8 C12 0.7(2) . . . . ?
C6 C7 C8 C12 -178.46(15) . . . . ?
O3 C7 C8 C9 177.36(14) . . . . ?
C6 C7 C8 C9 -1.8(2) . . . . ?
C7 C8 C9 O2 -177.20(17) . . . . ?
C12 C8 C9 O2 -0.8(3) . . . . ?
C7 C8 C9 O1 2.8(2) . . . . ?
C12 C8 C9 O1 179.25(14) . . . . ?
O4 C10 C11 C12 -179.30(18) . . . . ?
O3 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C8 -0.8(2) . . . . ?
C10 C11 C12 C13 178.81(15) . . . . ?
C7 C8 C12 C11 0.4(2) . . . . ?
C9 C8 C12 C11 -176.00(15) . . . . ?
C7 C8 C12 C13 -179.18(14) . . . . ?
C9 C8 C12 C13 4.4(2) . . . . ?
C11 C12 C13 C19 51.0(2) . . . . ?
C8 C12 C13 C19 -129.37(17) . . . . ?
C11 C12 C13 C14 -124.41(17) . . . . ?
C8 C12 C13 C14 55.2(2) . . . . ?
C19 C13 C14 C15 0.4(2) . . . . ?
C12 C13 C14 C15 175.91(15) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C18 -1.5(3) . . . . ?
C14 C15 C16 C17 178.13(17) . . . . ?
C15 C16 C18 C19 0.4(3) . . . . ?
C17 C16 C18 C19 -179.23(17) . . . . ?
C16 C18 C19 C13 1.1(3) . . . . ?
C14 C13 C19 C18 -1.5(2) . . . . ?
C12 C13 C19 C18 -177.13(15) . . . . ?
C6 C5 O1 C9 0.9(3) . . . . ?
C4 C5 O1 C9 -178.58(17) . . . . ?
O2 C9 O1 C5 177.57(15) . . . . ?
C8 C9 O1 C5 -2.4(2) . . . . ?
C8 C7 O3 C10 -1.5(2) . . . . ?
C6 C7 O3 C10 177.75(14) . . . . ?
O4 C10 O3 C7 -179.46(15) . . . . ?
C11 C10 O3 C7 1.1(2) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038



