# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_KA579_0m
_database_code_depnum_ccdc_archive 'CCDC 2008483'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-06-07 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 O4'
_chemical_formula_sum            'C17 H14 O4'
_chemical_formula_weight         282.28

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                   8.047(6)
_cell_length_b                   11.508(7)
_cell_length_c                   14.430(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.23(4)
_cell_angle_gamma                90
_cell_volume                     1336.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.265
_cell_measurement_theta_max      28.031

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7154
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26635
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3063
_reflns_number_gt                2331
_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 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0517P)²+0.5717P] 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         3063
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.4649(2) 0.31036(14) 0.30661(11) 0.0335(4) Uani 1 1 d . . . . .
C2 C 0.3794(2) 0.40295(14) 0.35997(11) 0.0328(4) Uani 1 1 d . . . . .
C3 C 0.3279(2) 0.38382(17) 0.45074(13) 0.0460(5) Uani 1 1 d . . . . .
H3 H 0.341181 0.311011 0.477728 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2572(3) 0.47305(19) 0.50030(13) 0.0523(5) Uani 1 1 d . . . . .
H4 H 0.222143 0.460093 0.560764 0.063 Uiso 1 1 calc R U . . .
C5 C 0.2377(3) 0.58179(18) 0.46104(13) 0.0499(5) Uani 1 1 d . . . . .
H5 H 0.191057 0.641821 0.495350 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2876(2) 0.60140(16) 0.37072(13) 0.0403(4) Uani 1 1 d . . . . .
H6 H 0.274425 0.674624 0.344445 0.048 Uiso 1 1 calc R U . . .
C7 C 0.35726(19) 0.51217(14) 0.31930(10) 0.0305(3) Uani 1 1 d . . . . .
C8 C 0.4100(2) 0.52891(14) 0.22005(11) 0.0313(4) Uani 1 1 d . . . . .
H8 H 0.341535 0.588054 0.189412 0.038 Uiso 1 1 calc R U . . .
C9 C 0.59724(19) 0.55865(13) 0.21191(10) 0.0291(3) Uani 1 1 d . . . . .
H9 H 0.630597 0.611858 0.261640 0.035 Uiso 1 1 calc R U . . .
C10 C 0.67748(18) 0.43857(13) 0.22669(10) 0.0261(3) Uani 1 1 d . . . . .
H10 H 0.720981 0.432693 0.290041 0.031 Uiso 1 1 calc R U . . .
C11 C 0.53026(18) 0.35231(13) 0.21346(10) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.5957(2) 0.25936(15) 0.14823(12) 0.0375(4) Uani 1 1 d . . . . .
H12A H 0.565077 0.182570 0.169966 0.045 Uiso 1 1 calc R U . . .
H12B H 0.551000 0.270204 0.086315 0.045 Uiso 1 1 calc R U . . .
C13 C 0.80895(19) 0.39545(14) 0.15746(12) 0.0333(4) Uani 1 1 d . . . . .
C14 C 0.9860(2) 0.40527(18) 0.19344(16) 0.0516(5) Uani 1 1 d . . . . .
H14A H 1.060943 0.372256 0.149042 0.077 Uiso 1 1 calc R U . . .
H14B H 0.995822 0.364143 0.251080 0.077 Uiso 1 1 calc R U . . .
H14C H 1.013169 0.485633 0.202942 0.077 Uiso 1 1 calc R U . . .
C15 C 0.7941(2) 0.45207(16) 0.06424(12) 0.0434(4) Uani 1 1 d . . . . .
H15 H 0.842646 0.414220 0.014259 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7175(2) 0.55135(17) 0.04741(12) 0.0447(5) Uani 1 1 d . . . . .
H16 H 0.722411 0.582207 -0.012084 0.054 Uiso 1 1 calc R U . . .
C17 C 0.6256(2) 0.61468(16) 0.11811(12) 0.0404(4) Uani 1 1 d . . . . .
O1 O 0.4851(2) 0.21198(11) 0.33455(10) 0.0591(4) Uani 1 1 d . . . . .
O2 O 0.39902(13) 0.41950(10) 0.17211(7) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.77226(14) 0.27263(10) 0.14823(8) 0.0382(3) Uani 1 1 d . . . . .
O4 O 0.5660(2) 0.70951(14) 0.10217(11) 0.0749(5) 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 O1 1.212(2) . ?
C1 C2 1.485(2) . ?
C1 C11 1.524(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.398(2) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.508(2) . ?
C8 O2 1.439(2) . ?
C8 C9 1.550(2) . ?
C8 H8 0.9800 . ?
C9 C17 1.517(2) . ?
C9 C10 1.540(2) . ?
C9 H9 0.9800 . ?
C10 C13 1.540(2) . ?
C10 C11 1.557(2) . ?
C10 H10 0.9800 . ?
C11 O2 1.437(2) . ?
C11 C12 1.520(2) . ?
C12 O3 1.429(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.450(2) . ?
C13 C15 1.499(3) . ?
C13 C14 1.519(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.320(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.458(3) . ?
C16 H16 0.9300 . ?
C17 O4 1.214(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
O1 C1 C2 124.00(16) . . ?
O1 C1 C11 122.89(15) . . ?
C2 C1 C11 113.09(14) . . ?
C3 C2 C7 119.92(16) . . ?
C3 C2 C1 120.96(16) . . ?
C7 C2 C1 119.07(14) . . ?
C4 C3 C2 119.75(18) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.60(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.06(17) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.18(17) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 119.48(15) . . ?
C6 C7 C8 121.99(15) . . ?
C2 C7 C8 118.53(14) . . ?
O2 C8 C7 109.14(13) . . ?
O2 C8 C9 102.39(12) . . ?
C7 C8 C9 112.19(13) . . ?
O2 C8 H8 110.9 . . ?
C7 C8 H8 110.9 . . ?
C9 C8 H8 110.9 . . ?
C17 C9 C10 116.13(13) . . ?
C17 C9 C8 108.13(13) . . ?
C10 C9 C8 101.45(12) . . ?
C17 C9 H9 110.2 . . ?
C10 C9 H9 110.2 . . ?
C8 C9 H9 110.2 . . ?
C9 C10 C13 119.22(13) . . ?
C9 C10 C11 103.70(13) . . ?
C13 C10 C11 103.85(12) . . ?
C9 C10 H10 109.8 . . ?
C13 C10 H10 109.8 . . ?
C11 C10 H10 109.8 . . ?
O2 C11 C12 112.17(13) . . ?
O2 C11 C1 106.34(12) . . ?
C12 C11 C1 116.42(14) . . ?
O2 C11 C10 105.39(13) . . ?
C12 C11 C10 105.01(13) . . ?
C1 C11 C10 111.04(12) . . ?
O3 C12 C11 105.78(13) . . ?
O3 C12 H12A 110.6 . . ?
C11 C12 H12A 110.6 . . ?
O3 C12 H12B 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
O3 C13 C15 109.01(14) . . ?
O3 C13 C14 107.12(14) . . ?
C15 C13 C14 110.24(15) . . ?
O3 C13 C10 103.51(12) . . ?
C15 C13 C10 112.91(14) . . ?
C14 C13 C10 113.59(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 125.23(16) . . ?
C16 C15 H15 117.4 . . ?
C13 C15 H15 117.4 . . ?
C15 C16 C17 122.79(16) . . ?
C15 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
O4 C17 C16 121.21(17) . . ?
O4 C17 C9 119.36(16) . . ?
C16 C17 C9 119.37(15) . . ?
C11 O2 C8 103.15(11) . . ?
C12 O3 C13 107.83(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
O1 C1 C2 C3 5.3(3) . . . . ?
C11 C1 C2 C3 -172.93(16) . . . . ?
O1 C1 C2 C7 -177.42(17) . . . . ?
C11 C1 C2 C7 4.3(2) . . . . ?
C7 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C4 176.44(18) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C2 -1.2(3) . . . . ?
C5 C6 C7 C8 178.67(16) . . . . ?
C3 C2 C7 C6 1.6(3) . . . . ?
C1 C2 C7 C6 -175.71(15) . . . . ?
C3 C2 C7 C8 -178.28(16) . . . . ?
C1 C2 C7 C8 4.4(2) . . . . ?
C6 C7 C8 O2 -151.98(15) . . . . ?
C2 C7 C8 O2 27.9(2) . . . . ?
C6 C7 C8 C9 95.26(18) . . . . ?
C2 C7 C8 C9 -84.90(18) . . . . ?
O2 C8 C9 C17 82.90(15) . . . . ?
C7 C8 C9 C17 -160.21(14) . . . . ?
O2 C8 C9 C10 -39.72(14) . . . . ?
C7 C8 C9 C10 77.16(15) . . . . ?
C17 C9 C10 C13 13.2(2) . . . . ?
C8 C9 C10 C13 130.15(14) . . . . ?
C17 C9 C10 C11 -101.54(16) . . . . ?
C8 C9 C10 C11 15.40(14) . . . . ?
O1 C1 C11 O2 136.55(17) . . . . ?
C2 C1 C11 O2 -45.16(17) . . . . ?
O1 C1 C11 C12 10.8(2) . . . . ?
C2 C1 C11 C12 -170.95(14) . . . . ?
O1 C1 C11 C10 -109.30(19) . . . . ?
C2 C1 C11 C10 68.98(17) . . . . ?
C9 C10 C11 O2 13.58(14) . . . . ?
C13 C10 C11 O2 -111.70(13) . . . . ?
C9 C10 C11 C12 132.21(13) . . . . ?
C13 C10 C11 C12 6.93(16) . . . . ?
C9 C10 C11 C1 -101.16(14) . . . . ?
C13 C10 C11 C1 133.56(13) . . . . ?
O2 C11 C12 O3 129.68(14) . . . . ?
C1 C11 C12 O3 -107.52(15) . . . . ?
C10 C11 C12 O3 15.72(16) . . . . ?
C9 C10 C13 O3 -141.38(14) . . . . ?
C11 C10 C13 O3 -26.70(15) . . . . ?
C9 C10 C13 C15 -23.7(2) . . . . ?
C11 C10 C13 C15 91.02(16) . . . . ?
C9 C10 C13 C14 102.82(17) . . . . ?
C11 C10 C13 C14 -142.51(14) . . . . ?
O3 C13 C15 C16 134.80(19) . . . . ?
C14 C13 C15 C16 -107.9(2) . . . . ?
C10 C13 C15 C16 20.4(3) . . . . ?
C13 C15 C16 C17 -4.8(3) . . . . ?
C15 C16 C17 O4 175.0(2) . . . . ?
C15 C16 C17 C9 -7.8(3) . . . . ?
C10 C9 C17 O4 -179.82(18) . . . . ?
C8 C9 C17 O4 67.0(2) . . . . ?
C10 C9 C17 C16 3.0(2) . . . . ?
C8 C9 C17 C16 -110.20(18) . . . . ?
C12 C11 O2 C8 -153.42(12) . . . . ?
C1 C11 O2 C8 78.26(14) . . . . ?
C10 C11 O2 C8 -39.69(14) . . . . ?
C7 C8 O2 C11 -69.07(15) . . . . ?
C9 C8 O2 C11 49.98(14) . . . . ?
C11 C12 O3 C13 -34.50(17) . . . . ?
C15 C13 O3 C12 -81.75(16) . . . . ?
C14 C13 O3 C12 158.98(14) . . . . ?
C10 C13 O3 C12 38.67(16) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
