# 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_KB1222_0m
_database_code_depnum_ccdc_archive 'CCDC 2308383'
loop_
_audit_author_name
_audit_author_address
'Dr. B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-01-19 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         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.33

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.7289(7)
_cell_length_b                   11.5281(9)
_cell_length_c                   13.9318(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1562.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.293
_cell_measurement_theta_max      30.0195

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6736
_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            26531
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         30.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4605
_reflns_number_gt                3964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.993

_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)+(0.0578P)²+0.1491P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4605
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.7689(3) 0.4773(3) 0.92632(18) 0.0655(7) Uani 1 1 d . . . . .
H1A H 0.729668 0.402701 0.939852 0.098 Uiso 1 1 calc R U . . .
H1B H 0.753683 0.528190 0.979830 0.098 Uiso 1 1 calc R U . . .
H1C H 0.865921 0.469107 0.915576 0.098 Uiso 1 1 calc R U . . .
C2 C 0.7021(2) 0.52771(19) 0.83762(14) 0.0438(4) Uani 1 1 d . . . . .
C3 C 0.7726(2) 0.6102(2) 0.78174(17) 0.0513(5) Uani 1 1 d . . . . .
H3 H 0.859469 0.634214 0.801132 0.062 Uiso 1 1 calc R U . . .
C4 C 0.7171(2) 0.6563(2) 0.69944(17) 0.0488(5) Uani 1 1 d . . . . .
H4 H 0.765462 0.710803 0.663678 0.059 Uiso 1 1 calc R U . . .
C5 C 0.58779(19) 0.61990(16) 0.67079(13) 0.0357(4) Uani 1 1 d . . . . .
C6 C 0.51418(17) 0.53879(15) 0.72454(12) 0.0316(3) Uani 1 1 d . . . . .
C7 C 0.57286(19) 0.49318(17) 0.80843(13) 0.0371(4) Uani 1 1 d . . . . .
H7 H 0.524283 0.439233 0.844661 0.045 Uiso 1 1 calc R U . . .
C8 C 0.38264(17) 0.50918(14) 0.68606(12) 0.0296(3) Uani 1 1 d . . . . .
C9 C 0.33502(17) 0.54947(15) 0.60094(11) 0.0304(3) Uani 1 1 d . . . . .
C10 C 0.41170(19) 0.63285(15) 0.54767(12) 0.0339(4) Uani 1 1 d . . . . .
C11 C 0.16882(18) 0.44306(15) 0.68089(12) 0.0331(3) Uani 1 1 d . . . . .
C12 C 0.0561(2) 0.40775(19) 0.72347(15) 0.0446(5) Uani 1 1 d . . . . .
H12A H 0.059607 0.380294 0.786196 0.054 Uiso 1 1 calc R U . . .
H12B H -0.027323 0.410165 0.690948 0.054 Uiso 1 1 calc R U . . .
C13 C 0.19456(18) 0.49599(15) 0.58152(12) 0.0303(3) Uani 1 1 d . . . . .
C14 C 0.0859(2) 0.58587(17) 0.55385(14) 0.0385(4) Uani 1 1 d . . . . .
H14A H 0.106741 0.617150 0.490875 0.046 Uiso 1 1 calc R U . . .
H14B H -0.003646 0.549043 0.550813 0.046 Uiso 1 1 calc R U . . .
C15 C 0.1970(2) 0.40270(15) 0.50207(13) 0.0348(4) Uani 1 1 d . . . . .
C16 C 0.0926(3) 0.3208(2) 0.49593(18) 0.0578(6) Uani 1 1 d . . . . .
H16 H 0.024363 0.319081 0.542640 0.069 Uiso 1 1 calc R U . . .
C17 C 0.0889(4) 0.2419(2) 0.4214(2) 0.0713(8) Uani 1 1 d . . . . .
H17 H 0.018043 0.187916 0.418231 0.086 Uiso 1 1 calc R U . . .
C18 C 0.1897(3) 0.2426(2) 0.35134(18) 0.0602(6) Uani 1 1 d . . . . .
H18 H 0.187346 0.188817 0.301596 0.072 Uiso 1 1 calc R U . . .
C19 C 0.2927(3) 0.3228(2) 0.35588(15) 0.0512(5) Uani 1 1 d . . . . .
H19 H 0.360190 0.324235 0.308610 0.061 Uiso 1 1 calc R U . . .
C20 C 0.2973(2) 0.40230(18) 0.43072(14) 0.0432(4) Uani 1 1 d . . . . .
H20 H 0.368395 0.456121 0.433216 0.052 Uiso 1 1 calc R U . . .
O1 O 0.53556(14) 0.66708(12) 0.58715(10) 0.0405(3) Uani 1 1 d . . . . .
O2 O 0.38202(16) 0.67756(13) 0.47094(10) 0.0452(4) Uani 1 1 d . . . . .
O3 O 0.29427(13) 0.43833(11) 0.73227(9) 0.0349(3) Uani 1 1 d . . . . .
O4 O 0.08290(18) 0.67668(14) 0.62181(11) 0.0497(4) Uani 1 1 d D . . . .
H4O H 0.035(3) 0.728(3) 0.597(2) 0.086(11) Uiso 1 1 d 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 1.513(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.380(3) . ?
C2 C3 1.407(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 O1 1.383(2) . ?
C5 C6 1.396(2) . ?
C6 C7 1.403(2) . ?
C6 C8 1.429(2) . ?
C7 H7 0.9300 . ?
C8 O3 1.3493(19) . ?
C8 C9 1.355(2) . ?
C9 C10 1.425(2) . ?
C9 C13 1.523(2) . ?
C10 O2 1.221(2) . ?
C10 O1 1.382(2) . ?
C11 C12 1.312(3) . ?
C11 O3 1.416(2) . ?
C11 C13 1.534(2) . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C13 C14 1.530(3) . ?
C13 C15 1.543(2) . ?
C14 O4 1.412(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.390(3) . ?
C15 C20 1.392(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O4 H4O 0.83(2) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.42(18) . . ?
C7 C2 C1 121.5(2) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C3 C2 122.1(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
O1 C5 C4 117.24(17) . . ?
O1 C5 C6 121.82(16) . . ?
C4 C5 C6 120.95(17) . . ?
C5 C6 C7 119.29(16) . . ?
C5 C6 C8 114.73(15) . . ?
C7 C6 C8 125.98(16) . . ?
C2 C7 C6 120.54(18) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
O3 C8 C9 114.03(15) . . ?
O3 C8 C6 122.43(15) . . ?
C9 C8 C6 123.54(16) . . ?
C8 C9 C10 120.52(16) . . ?
C8 C9 C13 108.87(14) . . ?
C10 C9 C13 130.54(15) . . ?
O2 C10 O1 115.72(16) . . ?
O2 C10 C9 128.06(17) . . ?
O1 C10 C9 116.22(15) . . ?
C12 C11 O3 118.69(16) . . ?
C12 C11 C13 131.94(17) . . ?
O3 C11 C13 109.33(14) . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C9 C13 C14 112.99(15) . . ?
C9 C13 C11 98.46(13) . . ?
C14 C13 C11 112.59(15) . . ?
C9 C13 C15 113.28(14) . . ?
C14 C13 C15 107.58(14) . . ?
C11 C13 C15 111.89(14) . . ?
O4 C14 C13 110.34(15) . . ?
O4 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
O4 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C20 117.76(18) . . ?
C16 C15 C13 120.40(18) . . ?
C20 C15 C13 121.68(16) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C10 O1 C5 122.92(14) . . ?
C8 O3 C11 106.54(12) . . ?
C14 O4 H4O 105(2) . . ?

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
C7 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 178.5(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 O1 -179.36(19) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
O1 C5 C6 C7 179.49(16) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
O1 C5 C6 C8 0.1(2) . . . . ?
C4 C5 C6 C8 -179.74(18) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 -178.3(2) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C8 C6 C7 C2 179.13(18) . . . . ?
C5 C6 C8 O3 -175.35(16) . . . . ?
C7 C6 C8 O3 5.4(3) . . . . ?
C5 C6 C8 C9 4.3(2) . . . . ?
C7 C6 C8 C9 -174.95(17) . . . . ?
O3 C8 C9 C10 174.68(15) . . . . ?
C6 C8 C9 C10 -5.0(3) . . . . ?
O3 C8 C9 C13 -2.6(2) . . . . ?
C6 C8 C9 C13 177.72(15) . . . . ?
C8 C9 C10 O2 -179.41(19) . . . . ?
C13 C9 C10 O2 -2.8(3) . . . . ?
C8 C9 C10 O1 1.1(2) . . . . ?
C13 C9 C10 O1 177.63(16) . . . . ?
C8 C9 C13 C14 130.23(15) . . . . ?
C10 C9 C13 C14 -46.7(2) . . . . ?
C8 C9 C13 C11 11.21(17) . . . . ?
C10 C9 C13 C11 -165.66(18) . . . . ?
C8 C9 C13 C15 -107.10(16) . . . . ?
C10 C9 C13 C15 76.0(2) . . . . ?
C12 C11 C13 C9 161.3(2) . . . . ?
O3 C11 C13 C9 -16.25(17) . . . . ?
C12 C11 C13 C14 42.0(3) . . . . ?
O3 C11 C13 C14 -135.56(15) . . . . ?
C12 C11 C13 C15 -79.3(3) . . . . ?
O3 C11 C13 C15 103.12(16) . . . . ?
C9 C13 C14 O4 -51.6(2) . . . . ?
C11 C13 C14 O4 58.9(2) . . . . ?
C15 C13 C14 O4 -177.37(16) . . . . ?
C9 C13 C15 C16 159.42(19) . . . . ?
C14 C13 C15 C16 -75.0(2) . . . . ?
C11 C13 C15 C16 49.2(2) . . . . ?
C9 C13 C15 C20 -25.1(2) . . . . ?
C14 C13 C15 C20 100.5(2) . . . . ?
C11 C13 C15 C20 -135.35(18) . . . . ?
C20 C15 C16 C17 0.0(4) . . . . ?
C13 C15 C16 C17 175.6(2) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
C16 C15 C20 C19 0.1(3) . . . . ?
C13 C15 C20 C19 -175.43(19) . . . . ?
O2 C10 O1 C5 -176.23(16) . . . . ?
C9 C10 O1 C5 3.4(3) . . . . ?
C4 C5 O1 C10 175.88(18) . . . . ?
C6 C5 O1 C10 -4.0(3) . . . . ?
C9 C8 O3 C11 -8.43(19) . . . . ?
C6 C8 O3 C11 171.29(15) . . . . ?
C12 C11 O3 C8 -161.99(18) . . . . ?
C13 C11 O3 C8 15.94(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4O O2 0.83(2) 2.07(2) 2.883(2) 166(3) 2_466 yes

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035

