# 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_KB824_0m
_database_code_depnum_ccdc_archive 'CCDC 2312115'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-07-05 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         'C18 H14 O4'
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29

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           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                   24.420(3)
_cell_length_b                   9.1758(11)
_cell_length_c                   13.2477(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.449(4)
_cell_angle_gamma                90
_cell_volume                     2949.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6299
_cell_measurement_theta_min      2.373
_cell_measurement_theta_max      28.6905

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6624
_exptl_absorpt_correction_T_max  0.7461
_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            17945
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         30.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4331
_reflns_number_gt                2319
_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)+(0.0786P)²+1.0665P] 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         4331
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1778
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.27183(8) 0.4976(2) 0.41946(15) 0.0657(5) Uani 1 1 d . . . . .
H1 H 0.284459 0.494582 0.355827 0.079 Uiso 1 1 calc R U . . .
C2 C 0.22614(8) 0.5801(2) 0.43324(18) 0.0761(6) Uani 1 1 d . . . . .
H2 H 0.207885 0.631220 0.378904 0.091 Uiso 1 1 calc R U . . .
C3 C 0.20731(9) 0.5869(2) 0.5283(2) 0.0771(6) Uani 1 1 d . . . . .
H3 H 0.177178 0.645260 0.537845 0.093 Uiso 1 1 calc R U . . .
C4 C 0.23288(8) 0.5082(2) 0.60799(17) 0.0694(5) Uani 1 1 d . . . . .
H4 H 0.220138 0.512495 0.671484 0.083 Uiso 1 1 calc R U . . .
C5 C 0.27776(7) 0.42244(19) 0.59313(13) 0.0556(4) Uani 1 1 d . . . . .
C6 C 0.29958(7) 0.41826(17) 0.49990(13) 0.0526(4) Uani 1 1 d . . . . .
C7 C 0.34873(7) 0.33119(16) 0.49229(12) 0.0484(4) Uani 1 1 d . . . . .
C8 C 0.36877(7) 0.25037(17) 0.57438(12) 0.0498(4) Uani 1 1 d . . . . .
C9 C 0.34340(7) 0.24899(19) 0.66868(13) 0.0547(4) Uani 1 1 d . . . . .
C10 C 0.41929(7) 0.15862(17) 0.57739(12) 0.0511(4) Uani 1 1 d . . . . .
C11 C 0.51560(8) 0.1523(3) 0.61972(18) 0.0789(6) Uani 1 1 d . . . . .
H11A H 0.524755 0.127414 0.553247 0.118 Uiso 1 1 calc R U . . .
H11B H 0.511603 0.064797 0.657957 0.118 Uiso 1 1 calc R U . . .
H11C H 0.544438 0.211109 0.653981 0.118 Uiso 1 1 calc R U . . .
C12 C 0.37564(7) 0.33275(16) 0.39669(12) 0.0492(4) Uani 1 1 d . . . . .
C13 C 0.39330(8) 0.46278(18) 0.35704(12) 0.0561(4) Uani 1 1 d . . . . .
H13 H 0.389053 0.549774 0.391332 0.067 Uiso 1 1 calc R U . . .
C14 C 0.41710(8) 0.46388(19) 0.26714(13) 0.0592(4) Uani 1 1 d . . . . .
H14 H 0.429486 0.551537 0.242739 0.071 Uiso 1 1 calc R U . . .
C15 C 0.42285(7) 0.33706(19) 0.21277(12) 0.0562(4) Uani 1 1 d . . . . .
C16 C 0.40561(8) 0.2074(2) 0.25292(13) 0.0610(5) Uani 1 1 d . . . . .
H16 H 0.409408 0.120748 0.217956 0.073 Uiso 1 1 calc R U . . .
C17 C 0.38287(8) 0.20459(18) 0.34404(13) 0.0560(4) Uani 1 1 d . . . . .
H17 H 0.372353 0.116138 0.370202 0.067 Uiso 1 1 calc R U . . .
C18 C 0.44707(10) 0.3395(2) 0.11270(14) 0.0768(6) Uani 1 1 d . . . . .
H18A H 0.420373 0.303417 0.059903 0.115 Uiso 1 1 calc R U . . .
H18B H 0.479336 0.279068 0.117433 0.115 Uiso 1 1 calc R U . . .
H18C H 0.456878 0.437675 0.097204 0.115 Uiso 1 1 calc R U . . .
O1 O 0.29948(5) 0.33949(13) 0.67451(9) 0.0619(3) Uani 1 1 d . . . . .
O2 O 0.35903(6) 0.17651(15) 0.74244(10) 0.0716(4) Uani 1 1 d . . . . .
O3 O 0.41954(6) 0.03188(14) 0.55482(12) 0.0757(4) Uani 1 1 d . . . . .
O4 O 0.46428(5) 0.23306(14) 0.61060(10) 0.0658(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 1.377(3) . ?
C1 C6 1.401(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 O1 1.376(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.455(2) . ?
C7 C8 1.361(2) . ?
C7 C12 1.491(2) . ?
C8 C9 1.455(2) . ?
C8 C10 1.491(2) . ?
C9 O2 1.208(2) . ?
C9 O1 1.366(2) . ?
C10 O3 1.201(2) . ?
C10 O4 1.326(2) . ?
C11 O4 1.449(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.389(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 C18 1.511(2) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 120.97(19) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.38(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.38(19) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O1 C5 C4 116.46(16) . . ?
O1 C5 C6 121.64(15) . . ?
C4 C5 C6 121.89(18) . . ?
C5 C6 C1 117.22(16) . . ?
C5 C6 C7 118.37(15) . . ?
C1 C6 C7 124.41(16) . . ?
C8 C7 C6 117.98(15) . . ?
C8 C7 C12 122.06(15) . . ?
C6 C7 C12 119.96(14) . . ?
C7 C8 C9 122.76(16) . . ?
C7 C8 C10 123.46(14) . . ?
C9 C8 C10 113.76(14) . . ?
O2 C9 O1 117.89(15) . . ?
O2 C9 C8 124.95(17) . . ?
O1 C9 C8 117.13(15) . . ?
O3 C10 O4 123.65(16) . . ?
O3 C10 C8 124.58(16) . . ?
O4 C10 C8 111.74(14) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.31(15) . . ?
C17 C12 C7 120.78(14) . . ?
C13 C12 C7 120.91(13) . . ?
C14 C13 C12 120.63(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.28(16) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 117.93(16) . . ?
C14 C15 C18 121.10(16) . . ?
C16 C15 C18 120.97(16) . . ?
C17 C16 C15 121.25(16) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 120.55(15) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 O1 C5 121.87(13) . . ?
C10 O4 C11 116.15(15) . . ?

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 0.8(3) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 O1 -176.23(16) . . . . ?
C3 C4 C5 C6 2.9(3) . . . . ?
O1 C5 C6 C1 174.98(15) . . . . ?
C4 C5 C6 C1 -4.1(2) . . . . ?
O1 C5 C6 C7 -4.3(2) . . . . ?
C4 C5 C6 C7 176.69(16) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C2 C1 C6 C7 -178.61(17) . . . . ?
C5 C6 C7 C8 4.4(2) . . . . ?
C1 C6 C7 C8 -174.79(16) . . . . ?
C5 C6 C7 C12 -175.44(14) . . . . ?
C1 C6 C7 C12 5.4(2) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C12 C7 C8 C9 179.24(14) . . . . ?
C6 C7 C8 C10 -178.86(14) . . . . ?
C12 C7 C8 C10 1.0(2) . . . . ?
C7 C8 C9 O2 178.24(17) . . . . ?
C10 C8 C9 O2 -3.3(2) . . . . ?
C7 C8 C9 O1 -3.5(2) . . . . ?
C10 C8 C9 O1 174.93(13) . . . . ?
C7 C8 C10 O3 -92.3(2) . . . . ?
C9 C8 C10 O3 89.3(2) . . . . ?
C7 C8 C10 O4 89.28(19) . . . . ?
C9 C8 C10 O4 -89.13(17) . . . . ?
C8 C7 C12 C17 58.0(2) . . . . ?
C6 C7 C12 C17 -122.22(17) . . . . ?
C8 C7 C12 C13 -123.12(18) . . . . ?
C6 C7 C12 C13 56.7(2) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C7 C12 C13 C14 -178.54(16) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C16 -2.1(3) . . . . ?
C13 C14 C15 C18 177.84(17) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C18 C15 C16 C17 -179.33(17) . . . . ?
C15 C16 C17 C12 1.4(3) . . . . ?
C13 C12 C17 C16 -1.9(3) . . . . ?
C7 C12 C17 C16 177.07(16) . . . . ?
O2 C9 O1 C5 -177.83(15) . . . . ?
C8 C9 O1 C5 3.8(2) . . . . ?
C4 C5 O1 C9 179.15(15) . . . . ?
C6 C5 O1 C9 0.1(2) . . . . ?
O3 C10 O4 C11 -0.5(2) . . . . ?
C8 C10 O4 C11 177.97(15) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037

