# 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_BS_GB2
_database_code_depnum_ccdc_archive 'CCDC 2074327'
loop_
_audit_author_name
_audit_author_address
'Dr. Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2021-03-30 deposited with the CCDC.	2021-07-16 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         ?
_chemical_formula_sum            'C20 H16 O5'
_chemical_formula_weight         336.33

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      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                   28.45(6)
_cell_length_b                   5.000(10)
_cell_length_c                   24.77(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.16(5)
_cell_angle_gamma                90
_cell_volume                     3349(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3148
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      20.14

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37388
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.625
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.000
_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             3288
_reflns_number_gt                1985
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)] 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_number_reflns         3288
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.454
_refine_ls_restrained_S_all      1.454
_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
O4 O 0.07329(6) 0.4825(3) 0.05013(6) 0.0710(5) Uani 1 1 d . . . . .
C1 C 0.15532(8) 0.5489(4) 0.12114(9) 0.0520(5) Uani 1 1 d . . . . .
C13 C 0.31605(7) 0.2777(4) 0.13954(8) 0.0472(5) Uani 1 1 d . . . . .
C4 C 0.09660(8) 0.2198(4) 0.13747(9) 0.0550(6) Uani 1 1 d . . . . .
C12 C 0.27702(7) 0.3951(4) 0.16012(9) 0.0537(5) Uani 1 1 d . . . . .
C17 C 0.35259(7) 0.1024(4) 0.17364(9) 0.0545(6) Uani 1 1 d . . . . .
H17 H 0.3514 0.0568 0.2104 0.065 Uiso 1 1 calc R U . . .
C18 C 0.39022(8) -0.0055(4) 0.15527(9) 0.0588(6) Uani 1 1 d . . . . .
C5 C 0.14374(8) 0.3596(4) 0.15459(9) 0.0520(5) Uani 1 1 d . . . . .
O5 O 0.28410(6) 0.5093(3) 0.04773(6) 0.0895(6) Uani 1 1 d . . . . .
C19 C 0.39113(8) 0.0677(5) 0.10002(10) 0.0677(6) Uani 1 1 d . . . . .
H19 H 0.4161 -0.0047 0.0862 0.081 Uiso 1 1 calc R U . . .
C14 C 0.31842(8) 0.3441(4) 0.08453(9) 0.0618(6) Uani 1 1 d . . . . .
C3 C 0.06197(9) 0.2932(5) 0.08473(10) 0.0617(6) Uani 1 1 d . . . . .
C11 C 0.24762(8) 0.6223(4) 0.12381(10) 0.0687(7) Uani 1 1 d . . . . .
H11 H 0.2708 0.7779 0.1313 0.082 Uiso 1 1 calc R U . . .
C20 C 0.35652(9) 0.2422(5) 0.06581(10) 0.0761(7) Uani 1 1 d . . . . .
H20 H 0.3587 0.2925 0.0297 0.091 Uiso 1 1 calc R U . . .
C10 C 0.20182(8) 0.7224(4) 0.13906(10) 0.0692(7) Uani 1 1 d . . . . .
H10A H 0.2117 0.7457 0.1808 0.083 Uiso 1 1 calc R U . . .
H10B H 0.1930 0.9015 0.1218 0.083 Uiso 1 1 calc R U . . .
C9 C 0.08274(11) 0.0188(5) 0.16984(11) 0.0770(7) Uani 1 1 d . . . . .
H9 H 0.1055 -0.0353 0.2051 0.092 Uiso 1 1 calc R U . . .
C8 C 0.03586(13) -0.1017(5) 0.15057(15) 0.0970(9) Uani 1 1 d . . . . .
H8 H 0.0269 -0.2378 0.1722 0.116 Uiso 1 1 calc R U . . .
C6 C 0.01504(10) 0.1775(6) 0.06568(12) 0.0839(8) Uani 1 1 d . . . . .
H6 H -0.0080 0.2315 0.0306 0.101 Uiso 1 1 calc R U . . .
C16 C 0.23858(9) 0.5526(5) 0.06210(10) 0.0879(8) Uani 1 1 d . . . . .
H16A H 0.2181 0.3886 0.0530 0.105 Uiso 1 1 calc R U . . .
H16B H 0.2196 0.6991 0.0382 0.105 Uiso 1 1 calc R U . . .
C7 C 0.00243(11) -0.0165(7) 0.09845(16) 0.1034(10) Uani 1 1 d . . . . .
H7 H -0.0296 -0.0944 0.0855 0.124 Uiso 1 1 calc R U . . .
C21 C 0.11828(9) 0.6181(5) 0.06611(10) 0.0636(6) Uani 1 1 d . . . . .
O3 O 0.26913(5) 0.3157(3) 0.20453(6) 0.0726(5) Uani 1 1 d . . . . .
O2 O 0.17470(6) 0.2873(3) 0.20743(6) 0.0692(5) Uani 1 1 d . . . . .
O1 O 0.12367(6) 0.7901(4) 0.03323(7) 0.0890(6) Uani 1 1 d . . . . .
C22 C 0.42915(8) -0.1968(5) 0.19206(10) 0.0860(8) Uani 1 1 d . . . . .
H22A H 0.4346 -0.1565 0.2323 0.129 Uiso 1 1 calc R U . . .
H22B H 0.4602 -0.1749 0.1833 0.129 Uiso 1 1 calc R U . . .
H22C H 0.4175 -0.3815 0.1842 0.129 Uiso 1 1 calc R U . . .
H3A H 0.2069(9) 0.351(5) 0.2074(10) 0.102(10) Uiso 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
O4 C3 1.381(3) . ?
O4 C21 1.392(4) . ?
C1 C5 1.364(3) . ?
C1 C21 1.481(4) . ?
C1 C10 1.528(4) . ?
C13 C17 1.420(3) . ?
C13 C14 1.424(4) . ?
C13 C12 1.480(3) . ?
C4 C9 1.416(3) . ?
C4 C3 1.418(4) . ?
C4 C5 1.454(4) . ?
C12 O3 1.254(3) . ?
C12 C11 1.526(3) . ?
C17 C18 1.396(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.425(4) . ?
C18 C22 1.531(3) . ?
C5 O2 1.379(3) . ?
O5 C14 1.383(3) . ?
O5 C16 1.462(4) . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C14 C20 1.401(4) . ?
C3 C6 1.395(4) . ?
C11 C16 1.510(5) . ?
C11 C10 1.549(4) . ?
C11 H11 1.0000 . ?
C20 H20 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C9 C8 1.405(4) . ?
C9 H9 0.9500 . ?
C8 C7 1.410(4) . ?
C8 H8 0.9500 . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C7 H7 0.9500 . ?
C21 O1 1.227(3) . ?
O2 H3A 0.97(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C3 O4 C21 121.9(2) . . ?
C5 C1 C21 118.9(2) . . ?
C5 C1 C10 124.7(2) . . ?
C21 C1 C10 116.0(2) . . ?
C17 C13 C14 118.0(2) . . ?
C17 C13 C12 121.9(2) . . ?
C14 C13 C12 120.1(2) . . ?
C9 C4 C3 118.0(3) . . ?
C9 C4 C5 124.8(2) . . ?
C3 C4 C5 117.2(2) . . ?
O3 C12 C13 122.4(2) . . ?
O3 C12 C11 122.5(2) . . ?
C13 C12 C11 115.1(2) . . ?
C18 C17 C13 122.6(2) . . ?
C18 C17 H17 118.7 . . ?
C13 C17 H17 118.7 . . ?
C17 C18 C19 117.3(2) . . ?
C17 C18 C22 122.3(2) . . ?
C19 C18 C22 120.4(2) . . ?
C1 C5 O2 123.7(2) . . ?
C1 C5 C4 122.1(2) . . ?
O2 C5 C4 114.2(2) . . ?
C14 O5 C16 115.2(2) . . ?
C20 C19 C18 121.7(2) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
O5 C14 C20 117.3(2) . . ?
O5 C14 C13 122.4(2) . . ?
C20 C14 C13 120.3(2) . . ?
O4 C3 C6 117.3(3) . . ?
O4 C3 C4 121.3(2) . . ?
C6 C3 C4 121.4(3) . . ?
C16 C11 C12 108.3(2) . . ?
C16 C11 C10 115.5(2) . . ?
C12 C11 C10 116.4(2) . . ?
C16 C11 H11 105.1 . . ?
C12 C11 H11 105.1 . . ?
C10 C11 H11 105.1 . . ?
C19 C20 C14 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C14 C20 H20 120.0 . . ?
C1 C10 C11 117.6(2) . . ?
C1 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
C1 C10 H10B 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C7 C6 C3 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C3 C6 H6 120.4 . . ?
O5 C16 C11 113.4(2) . . ?
O5 C16 H16A 108.9 . . ?
C11 C16 H16A 108.9 . . ?
O5 C16 H16B 108.9 . . ?
C11 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
O1 C21 O4 116.5(2) . . ?
O1 C21 C1 125.1(3) . . ?
O4 C21 C1 118.4(2) . . ?
C5 O2 H3A 103.8(14) . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036



