# 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 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_1
_database_code_depnum_ccdc_archive 'CCDC 2069443'
loop_
_audit_author_name
_audit_author_address
'Uday Narayan  Guria'
;Indian Institute of  Engineering Science and Technology, Shibpur
India
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-07-28 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         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26

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                   22.5345(18)
_cell_length_b                   7.6383(6)
_cell_length_c                   14.4857(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.381(2)
_cell_angle_gamma                90
_cell_volume                     2366.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    28173
_cell_measurement_theta_min      2.832
_cell_measurement_theta_max      25.051

_exptl_crystal_description       Cubic
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28173
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.832
_diffrn_reflns_theta_max         25.051
_diffrn_reflns_theta_full        25.051
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2093
_reflns_number_gt                1647
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0789P)²+3.9770P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0129(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2093
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O8 O 0.56848(7) 0.6227(2) 0.69610(12) 0.0488(5) Uani 1 1 d . . . . .
O16 O 0.39248(8) 0.3092(2) 0.52089(15) 0.0659(6) Uani 1 1 d . . . . .
O1 O 0.73712(9) 0.5570(3) 0.88476(15) 0.0775(7) Uani 1 1 d . . . . .
C9 C 0.50869(10) 0.6295(3) 0.63238(16) 0.0410(6) Uani 1 1 d . . . . .
C7 C 0.60204(11) 0.7722(3) 0.72947(16) 0.0418(6) Uani 1 1 d . . . . .
C10 C 0.48113(11) 0.7885(3) 0.59607(17) 0.0444(6) Uani 1 1 d . . . . .
C2 C 0.66039(11) 0.7531(3) 0.79355(17) 0.0469(6) Uani 1 1 d . . . . .
C14 C 0.41832(11) 0.4712(3) 0.54189(17) 0.0477(6) Uani 1 1 d . . . . .
C15 C 0.47836(11) 0.4731(3) 0.60697(18) 0.0478(6) Uani 1 1 d . . . . .
H15 H 0.4979 0.3690 0.6332 0.057 Uiso 1 1 calc R U . . .
C13 C 0.38924(11) 0.6265(3) 0.50361(18) 0.0522(7) Uani 1 1 d . . . . .
H13 H 0.3489 0.6257 0.4600 0.063 Uiso 1 1 calc R U . . .
C12 C 0.42073(11) 0.7822(3) 0.53087(19) 0.0531(7) Uani 1 1 d . . . . .
H12 H 0.4010 0.8863 0.5049 0.064 Uiso 1 1 calc R U . . .
C1 C 0.68523(12) 0.5831(4) 0.82727(19) 0.0569(7) Uani 1 1 d . . . . .
H1 H 0.6600 0.4863 0.8036 0.068 Uiso 1 1 calc R U . . .
C6 C 0.57386(12) 0.9391(3) 0.69420(19) 0.0564(7) Uani 1 1 d . . . . .
C11 C 0.51665(12) 0.9446(3) 0.6295(2) 0.0580(7) Uani 1 1 d . . . . .
H11 H 0.4994 1.0524 0.6054 0.070 Uiso 1 1 calc R U . . .
C3 C 0.70028(12) 0.9102(4) 0.8325(2) 0.0628(8) Uani 1 1 d . . . . .
H3A H 0.7077 0.9178 0.9020 0.075 Uiso 1 1 calc R U . . .
H3B H 0.7404 0.8952 0.8221 0.075 Uiso 1 1 calc R U . . .
C17 C 0.32892(12) 0.2980(4) 0.4602(2) 0.0646(8) Uani 1 1 d . . . . .
H17A H 0.3029 0.3632 0.4890 0.097 Uiso 1 1 calc R U . . .
H17B H 0.3160 0.1776 0.4535 0.097 Uiso 1 1 calc R U . . .
H17C H 0.3251 0.3455 0.3973 0.097 Uiso 1 1 calc R U . . .
C5 C 0.61284(18) 1.0964(4) 0.7357(3) 0.1168(18) Uani 1 1 d . . . . .
H5A H 0.6114 1.1741 0.6821 0.140 Uiso 1 1 calc R U . . .
H5B H 0.5928 1.1571 0.7767 0.140 Uiso 1 1 calc R U . . .
C4 C 0.67208(18) 1.0741(4) 0.7869(5) 0.158(3) Uani 1 1 d . . . . .
H4A H 0.6810 1.1599 0.8389 0.189 Uiso 1 1 calc R U . . .
H4B H 0.6959 1.1095 0.7448 0.189 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
O8 C7 1.370(3) . ?
O8 C9 1.373(3) . ?
O16 C14 1.360(3) . ?
O16 C17 1.427(3) . ?
O1 C1 1.219(3) . ?
C9 C15 1.368(3) . ?
C9 C10 1.390(3) . ?
C7 C2 1.357(3) . ?
C7 C6 1.444(3) . ?
C10 C12 1.391(3) . ?
C10 C11 1.433(3) . ?
C2 C1 1.438(3) . ?
C2 C3 1.499(4) . ?
C14 C13 1.384(3) . ?
C14 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C13 C12 1.378(4) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1 0.9300 . ?
C6 C11 1.334(3) . ?
C6 C5 1.498(4) . ?
C11 H11 0.9300 . ?
C3 C4 1.463(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 C4 1.318(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

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
C7 O8 C9 121.43(17) . . ?
C14 O16 C17 117.9(2) . . ?
C15 C9 O8 116.71(19) . . ?
C15 C9 C10 122.4(2) . . ?
O8 C9 C10 120.91(19) . . ?
C2 C7 O8 117.4(2) . . ?
C2 C7 C6 124.0(2) . . ?
O8 C7 C6 118.6(2) . . ?
C9 C10 C12 116.9(2) . . ?
C9 C10 C11 117.7(2) . . ?
C12 C10 C11 125.5(2) . . ?
C7 C2 C1 121.2(2) . . ?
C7 C2 C3 120.6(2) . . ?
C1 C2 C3 118.2(2) . . ?
O16 C14 C13 125.1(2) . . ?
O16 C14 C15 114.8(2) . . ?
C13 C14 C15 120.1(2) . . ?
C9 C15 C14 119.4(2) . . ?
C9 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C12 C10 122.0(2) . . ?
C13 C12 H12 119.0 . . ?
C10 C12 H12 119.0 . . ?
O1 C1 C2 124.5(3) . . ?
O1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C11 C6 C7 119.7(2) . . ?
C11 C6 C5 124.8(2) . . ?
C7 C6 C5 115.4(2) . . ?
C6 C11 C10 121.6(2) . . ?
C6 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C4 C3 C2 113.1(2) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5A 107.6 . . ?
C6 C5 H5A 107.6 . . ?
C4 C5 H5B 107.6 . . ?
C6 C5 H5B 107.6 . . ?
H5A C5 H5B 107.0 . . ?
C5 C4 C3 125.7(3) . . ?
C5 C4 H4A 105.9 . . ?
C3 C4 H4A 105.9 . . ?
C5 C4 H4B 105.9 . . ?
C3 C4 H4B 105.9 . . ?
H4A C4 H4B 106.2 . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.056

