# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2084126'
loop_
_audit_author_name
_audit_author_address
'Beneesh P Babu'
;National Institute of Technology Karnataka
India
;
_audit_update_record             
;
2021-05-16 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 O7'
_chemical_formula_sum            'C17 H14 O7'
_chemical_formula_weight         330.28

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.2678(7)
_cell_length_b                   13.2735(14)
_cell_length_c                   18.564(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.548(4)
_cell_angle_gamma                90
_cell_volume                     1544.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5124
_cell_measurement_theta_min      5.355
_cell_measurement_theta_max      56.564

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12619
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.194
_diffrn_reflns_theta_max         28.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3793
_reflns_number_gt                2831
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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)+(0.0881P)²+0.3475P] 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         3793
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.014
_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 0.5527(3) 0.61910(14) 0.55448(11) 0.0529(5) Uani 1 1 d . . . . .
H1 H 0.4310 0.5796 0.5489 0.063 Uiso 1 1 calc R U . . .
C2 C 0.7138(4) 0.58738(16) 0.59851(12) 0.0623(5) Uani 1 1 d . . . . .
H2 H 0.7010 0.5263 0.6226 0.075 Uiso 1 1 calc R U . . .
C3 C 0.8985(4) 0.64522(17) 0.60807(12) 0.0630(6) Uani 1 1 d . . . . .
H3 H 1.0071 0.6224 0.6384 0.076 Uiso 1 1 calc R U . . .
C4 C 0.9201(3) 0.73462(15) 0.57325(10) 0.0510(4) Uani 1 1 d . . . . .
H4 H 1.0434 0.7726 0.5800 0.061 Uiso 1 1 calc R U . . .
C5 C 0.7566(3) 0.77037(13) 0.52683(8) 0.0382(4) Uani 1 1 d . . . . .
C6 C 0.5686(3) 0.71163(12) 0.51707(8) 0.0395(4) Uani 1 1 d . . . . .
C7 C 0.4033(3) 0.74795(13) 0.47172(8) 0.0393(4) Uani 1 1 d . . . . .
H7 H 0.2792 0.7105 0.4652 0.047 Uiso 1 1 calc R U . . .
C8 C 0.4263(2) 0.83743(12) 0.43779(7) 0.0343(3) Uani 1 1 d . . . . .
C9 C 0.6129(2) 0.89608(11) 0.44602(7) 0.0321(3) Uani 1 1 d . . . . .
C10 C 0.7745(2) 0.86259(12) 0.48997(8) 0.0363(3) Uani 1 1 d . . . . .
H8 H 0.8974 0.9012 0.4955 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6289(2) 0.99297(11) 0.40857(7) 0.0326(3) Uani 1 1 d . . . . .
C12 C 0.3319(2) 0.93438(12) 0.33745(8) 0.0337(3) Uani 1 1 d . . . . .
C13 C 0.4581(2) 0.86486(12) 0.28708(8) 0.0342(3) Uani 1 1 d . . . . .
C14 C 0.1371(3) 0.98249(13) 0.30364(9) 0.0414(4) Uani 1 1 d . . . . .
H14A H 0.0303 0.9310 0.2947 0.050 Uiso 1 1 calc R U . . .
H14B H 0.0776 1.0307 0.3372 0.050 Uiso 1 1 calc R U . . .
C15 C 0.1855(3) 1.03497(13) 0.23429(9) 0.0412(4) Uani 1 1 d . . . . .
C16 C 0.4138(4) 0.72257(15) 0.21165(11) 0.0597(5) Uani 1 1 d . . . . .
H16A H 0.5330 0.7490 0.1856 0.090 Uiso 1 1 calc R U . . .
H16B H 0.3072 0.6991 0.1782 0.090 Uiso 1 1 calc R U . . .
H16C H 0.4606 0.6676 0.2415 0.090 Uiso 1 1 calc R U . . .
C17 C 0.0694(4) 1.1573(2) 0.15120(14) 0.0813(8) Uani 1 1 d . . . . .
H17A H 0.2072 1.1889 0.1515 0.122 Uiso 1 1 calc R U . . .
H17B H -0.0394 1.2078 0.1461 0.122 Uiso 1 1 calc R U . . .
H17C H 0.0601 1.1109 0.1116 0.122 Uiso 1 1 calc R U . . .
O1 O 0.46698(17) 1.01450(8) 0.36110(6) 0.0369(3) Uani 1 1 d . . . . .
O2 O 0.0397(2) 1.10330(12) 0.21830(9) 0.0684(4) Uani 1 1 d . . . . .
O3 O 0.3350(2) 1.01739(12) 0.19712(8) 0.0634(4) Uani 1 1 d . . . . .
O4 O 0.76278(18) 1.05562(9) 0.41856(6) 0.0443(3) Uani 1 1 d . . . . .
O5 O 0.26049(17) 0.87565(9) 0.39619(6) 0.0393(3) Uani 1 1 d . . . . .
O6 O 0.32447(19) 0.80078(9) 0.25626(7) 0.0476(3) Uani 1 1 d . . . . .
O7 O 0.64637(18) 0.86565(10) 0.28152(6) 0.0498(3) 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 1.360(3) . ?
C1 C6 1.415(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.399(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(2) . ?
C4 H4 0.9300 . ?
C5 C10 1.407(2) . ?
C5 C6 1.423(2) . ?
C6 C7 1.413(2) . ?
C7 C8 1.353(2) . ?
C7 H7 0.9300 . ?
C8 O5 1.3851(18) . ?
C8 C9 1.412(2) . ?
C9 C10 1.368(2) . ?
C9 C11 1.466(2) . ?
C10 H8 0.9300 . ?
C11 O4 1.1948(17) . ?
C11 O1 1.3677(18) . ?
C12 O5 1.4164(18) . ?
C12 O1 1.4261(17) . ?
C12 C14 1.509(2) . ?
C12 C13 1.538(2) . ?
C13 O7 1.1854(18) . ?
C13 O6 1.3204(18) . ?
C14 C15 1.497(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O3 1.192(2) . ?
C15 O2 1.319(2) . ?
C16 O6 1.444(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O2 1.451(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 120.55(18) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 121.01(18) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.33(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.52(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C5 C4 121.81(15) . . ?
C10 C5 C6 118.98(14) . . ?
C4 C5 C6 119.21(15) . . ?
C7 C6 C1 122.26(16) . . ?
C7 C6 C5 119.35(14) . . ?
C1 C6 C5 118.38(16) . . ?
C8 C7 C6 119.74(14) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 O5 119.90(13) . . ?
C7 C8 C9 121.70(14) . . ?
O5 C8 C9 118.34(14) . . ?
C10 C9 C8 119.52(14) . . ?
C10 C9 C11 120.96(13) . . ?
C8 C9 C11 119.51(13) . . ?
C9 C10 C5 120.69(14) . . ?
C9 C10 H8 119.7 . . ?
C5 C10 H8 119.7 . . ?
O4 C11 O1 118.05(14) . . ?
O4 C11 C9 126.02(14) . . ?
O1 C11 C9 115.81(12) . . ?
O5 C12 O1 111.37(11) . . ?
O5 C12 C14 107.03(12) . . ?
O1 C12 C14 106.75(12) . . ?
O5 C12 C13 107.82(12) . . ?
O1 C12 C13 109.09(12) . . ?
C14 C12 C13 114.82(12) . . ?
O7 C13 O6 126.57(15) . . ?
O7 C13 C12 124.47(14) . . ?
O6 C13 C12 108.78(13) . . ?
C15 C14 C12 112.62(14) . . ?
C15 C14 H14A 109.1 . . ?
C12 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C12 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
O3 C15 O2 123.43(17) . . ?
O3 C15 C14 124.99(15) . . ?
O2 C15 C14 111.58(16) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 O1 C12 118.51(12) . . ?
C15 O2 C17 116.01(18) . . ?
C8 O5 C12 112.95(11) . . ?
C13 O6 C16 117.62(14) . . ?

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(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C10 -179.92(19) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C7 -178.99(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C10 C5 C6 C7 -1.1(2) . . . . ?
C4 C5 C6 C7 178.91(16) . . . . ?
C10 C5 C6 C1 -179.98(16) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C1 C6 C7 C8 179.39(16) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C6 C7 C8 O5 -176.76(14) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
O5 C8 C9 C10 176.46(13) . . . . ?
C7 C8 C9 C11 -179.41(14) . . . . ?
O5 C8 C9 C11 -2.2(2) . . . . ?
C8 C9 C10 C5 0.1(2) . . . . ?
C11 C9 C10 C5 178.81(14) . . . . ?
C4 C5 C10 C9 -179.24(16) . . . . ?
C6 C5 C10 C9 0.7(2) . . . . ?
C10 C9 C11 O4 -9.7(2) . . . . ?
C8 C9 C11 O4 168.94(15) . . . . ?
C10 C9 C11 O1 174.28(13) . . . . ?
C8 C9 C11 O1 -7.0(2) . . . . ?
O5 C12 C13 O7 -106.34(17) . . . . ?
O1 C12 C13 O7 14.7(2) . . . . ?
C14 C12 C13 O7 134.48(17) . . . . ?
O5 C12 C13 O6 68.99(15) . . . . ?
O1 C12 C13 O6 -169.93(12) . . . . ?
C14 C12 C13 O6 -50.19(17) . . . . ?
O5 C12 C14 C15 -171.71(13) . . . . ?
O1 C12 C14 C15 68.94(16) . . . . ?
C13 C12 C14 C15 -52.09(18) . . . . ?
C12 C14 C15 O3 22.2(2) . . . . ?
C12 C14 C15 O2 -158.53(15) . . . . ?
O4 C11 O1 C12 167.31(13) . . . . ?
C9 C11 O1 C12 -16.36(18) . . . . ?
O5 C12 O1 C11 48.04(17) . . . . ?
C14 C12 O1 C11 164.54(12) . . . . ?
C13 C12 O1 C11 -70.85(15) . . . . ?
O3 C15 O2 C17 0.4(3) . . . . ?
C14 C15 O2 C17 -178.83(17) . . . . ?
C7 C8 O5 C12 -148.86(14) . . . . ?
C9 C8 O5 C12 33.91(18) . . . . ?
O1 C12 O5 C8 -55.90(16) . . . . ?
C14 C12 O5 C8 -172.23(12) . . . . ?
C13 C12 O5 C8 63.74(14) . . . . ?
O7 C13 O6 C16 0.7(2) . . . . ?
C12 C13 O6 C16 -174.51(14) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054

