# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_HAK_A_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2149586'
loop_
_audit_author_name
_audit_author_address
'Hilal Ahmad Khan'
;Pondicherry University
India
;
_audit_update_record             
;
2022-02-01 deposited with the CCDC.	2022-09-23 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         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.8517(5)
_cell_length_b                   10.0871(5)
_cell_length_c                   10.0861(5)
_cell_angle_alpha                86.084(2)
_cell_angle_beta                 71.973(2)
_cell_angle_gamma                64.392(2)
_cell_volume                     856.98(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34491
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.870
_diffrn_reflns_theta_max         26.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3478
_reflns_number_gt                2849
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_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)+(0.0457P)²+0.2358P] 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         3478
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1 O 0.63229(11) 0.38444(11) 0.25303(9) 0.0458(3) Uani 1 1 d . . . . .
O2 O 0.57834(15) 0.24878(13) 0.73096(12) 0.0692(4) Uani 1 1 d . . . . .
O3 O 0.44000(14) 0.41821(15) 0.16357(11) 0.0679(4) Uani 1 1 d . . . . .
O4 O 0.76816(19) 0.04110(16) 0.61564(15) 0.1021(6) Uani 1 1 d . . . . .
C1 C 0.11520(15) 0.53775(15) 0.58137(14) 0.0426(3) Uani 1 1 d . . . . .
C2 C -0.00595(17) 0.68015(17) 0.61653(16) 0.0524(4) Uani 1 1 d . . . . .
H2 H -0.009703 0.751308 0.552278 0.063 Uiso 1 1 calc R U . . .
C3 C -0.12054(18) 0.71671(19) 0.74582(18) 0.0609(4) Uani 1 1 d . . . . .
H3 H -0.199517 0.812755 0.768610 0.073 Uiso 1 1 calc R U . . .
C4 C -0.11892(19) 0.61263(19) 0.84094(17) 0.0599(4) Uani 1 1 d . . . . .
H4 H -0.196201 0.638036 0.928013 0.072 Uiso 1 1 calc R U . . .
C5 C -0.00263(18) 0.47069(19) 0.80699(17) 0.0571(4) Uani 1 1 d . . . . .
H5 H -0.002332 0.399656 0.870876 0.069 Uiso 1 1 calc R U . . .
C6 C 0.11404(17) 0.43259(16) 0.67852(15) 0.0486(3) Uani 1 1 d . . . . .
H6 H 0.192315 0.336173 0.656704 0.058 Uiso 1 1 calc R U . . .
C7 C 0.23555(16) 0.50375(15) 0.44385(14) 0.0443(3) Uani 1 1 d . . . . .
H7 H 0.200801 0.552164 0.370558 0.053 Uiso 1 1 calc R U . . .
C8 C 0.38982(15) 0.41117(14) 0.41101(13) 0.0385(3) Uani 1 1 d . . . . .
C9 C 0.48720(16) 0.40329(15) 0.26232(13) 0.0429(3) Uani 1 1 d . . . . .
C10 C 0.7372(2) 0.3739(2) 0.11467(16) 0.0661(5) Uani 1 1 d . . . . .
H10A H 0.829494 0.380749 0.120459 0.099 Uiso 1 1 calc R U . . .
H10B H 0.684039 0.452874 0.063828 0.099 Uiso 1 1 calc R U . . .
H10C H 0.768377 0.281140 0.067193 0.099 Uiso 1 1 calc R U . . .
C11 C 0.46564(15) 0.33553(14) 0.51605(13) 0.0387(3) Uani 1 1 d . . . . .
H11 H 0.422115 0.385460 0.604095 0.046 Uiso 1 1 calc R U . . .
C12 C 0.58935(15) 0.20395(14) 0.50134(13) 0.0408(3) Uani 1 1 d . . . . .
C13 C 0.65694(18) 0.15445(16) 0.61841(15) 0.0513(4) Uani 1 1 d . . . . .
C14 C 0.6369(3) 0.2117(2) 0.8486(2) 0.0907(7) Uani 1 1 d . . . . .
H14A H 0.562093 0.279682 0.927460 0.136 Uiso 1 1 calc R U . . .
H14B H 0.736366 0.217082 0.825975 0.136 Uiso 1 1 calc R U . . .
H14C H 0.651442 0.113355 0.871004 0.136 Uiso 1 1 calc R U . . .
C15 C 0.66497(17) 0.10165(15) 0.37325(14) 0.0460(3) Uani 1 1 d . . . . .
C16 C 0.8273(2) 0.04013(19) 0.30671(18) 0.0642(4) Uani 1 1 d . . . . .
H16 H 0.893064 0.056490 0.346101 0.077 Uiso 1 1 calc R U . . .
C17 C 0.8914(2) -0.0453(2) 0.1821(2) 0.0826(6) Uani 1 1 d . . . . .
H17 H 0.999984 -0.084584 0.137389 0.099 Uiso 1 1 calc R U . . .
C18 C 0.7976(3) -0.0730(2) 0.1237(2) 0.0826(6) Uani 1 1 d . . . . .
H18 H 0.841821 -0.129779 0.039203 0.099 Uiso 1 1 calc R U . . .
C19 C 0.6385(3) -0.0168(2) 0.1899(2) 0.0755(5) Uani 1 1 d . . . . .
H19 H 0.574559 -0.036971 0.151192 0.091 Uiso 1 1 calc R U . . .
C20 C 0.5714(2) 0.07032(17) 0.31484(16) 0.0569(4) Uani 1 1 d . . . . .
H20 H 0.462841 0.107774 0.359425 0.068 Uiso 1 1 calc R U . . .


_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
O1 C9 1.3314(16) . ?
O1 C10 1.4353(17) . ?
O2 C13 1.3268(18) . ?
O2 C14 1.4340(19) . ?
O3 C9 1.1986(16) . ?
O4 C13 1.1879(18) . ?
C1 C2 1.393(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.4639(19) . ?
C2 C3 1.380(2) . ?
C3 C4 1.371(2) . ?
C4 C5 1.373(2) . ?
C5 C6 1.383(2) . ?
C7 C8 1.3400(18) . ?
C8 C11 1.4660(17) . ?
C8 C9 1.4952(18) . ?
C11 C12 1.3363(18) . ?
C12 C13 1.4851(19) . ?
C12 C15 1.4869(18) . ?
C15 C20 1.382(2) . ?
C15 C16 1.389(2) . ?
C16 C17 1.381(2) . ?
C17 C18 1.364(3) . ?
C18 C19 1.363(3) . ?
C19 C20 1.390(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
C9 O1 C10 116.41(11) . . ?
C13 O2 C14 117.30(14) . . ?
C2 C1 C6 118.10(13) . . ?
C2 C1 C7 119.01(13) . . ?
C6 C1 C7 122.88(13) . . ?
C3 C2 C1 120.64(14) . . ?
C4 C3 C2 120.56(15) . . ?
C3 C4 C5 119.68(15) . . ?
C4 C5 C6 120.49(15) . . ?
C5 C6 C1 120.49(14) . . ?
C8 C7 C1 127.72(12) . . ?
C7 C8 C11 122.85(12) . . ?
C7 C8 C9 116.16(12) . . ?
C11 C8 C9 120.53(11) . . ?
O3 C9 O1 123.63(12) . . ?
O3 C9 C8 124.85(13) . . ?
O1 C9 C8 111.44(11) . . ?
C12 C11 C8 128.24(12) . . ?
C11 C12 C13 119.16(12) . . ?
C11 C12 C15 123.77(12) . . ?
C13 C12 C15 117.08(12) . . ?
O4 C13 O2 121.93(14) . . ?
O4 C13 C12 124.74(14) . . ?
O2 C13 C12 113.31(12) . . ?
C20 C15 C16 118.47(14) . . ?
C20 C15 C12 119.50(13) . . ?
C16 C15 C12 121.98(14) . . ?
C17 C16 C15 120.09(18) . . ?
C18 C17 C16 120.97(19) . . ?
C19 C18 C17 119.56(17) . . ?
C18 C19 C20 120.46(18) . . ?
C15 C20 C19 120.39(17) . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.027


_exptl_crystal_recrystallization_method 'Slow Evaporation'
