# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_9a
_database_code_depnum_ccdc_archive 'CCDC 1872034'
loop_
_audit_author_name
_audit_author_address
'Eshani Das'
;IIT Kharagpur
India
;
_audit_update_record             
;
2018-10-08 deposited with the CCDC.	2020-04-20 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            'C40 H32 N0 O12'
_chemical_formula_weight         704.65

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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   18.987(4)
_cell_length_b                   25.021(6)
_cell_length_c                   7.0870(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3366.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    400
_cell_measurement_theta_min      3.174
_cell_measurement_theta_max      28.455

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8727
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.174
_diffrn_reflns_theta_max         28.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2030
_reflns_number_gt                1526
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    0.918

_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e'
_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)+(0.0648P)²+1.1827P] 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_abs_structure_details 
;
 Flack x determined using 545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2030
_refine_ls_number_parameters     122
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.11975(10) 0.35438(6) 0.1628(4) 0.0598(5) Uani 1 1 d . . . . .
O3 O 0.13960(10) 0.21404(6) 0.1893(4) 0.0623(6) Uani 1 1 d . . . . .
C9 C 0.04578(13) 0.27923(9) 0.1729(5) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.11306(13) 0.26351(8) 0.1797(5) 0.0468(6) Uani 1 1 d . . . . .
O2 O 0.22261(10) 0.31225(8) 0.1778(6) 0.0769(7) Uani 1 1 d . . . . .
C2 C -0.01905(11) 0.24824(10) 0.1735(5) 0.0464(6) Uani 1 1 d . . . . .
C3 C -0.01913(14) 0.19274(11) 0.1571(5) 0.0539(7) Uani 1 1 d . . . . .
H3 H 0.0234 0.1744 0.1485 0.065 Uiso 1 1 calc R U . . .
C16 C 0.04672(14) 0.33884(10) 0.1620(6) 0.0521(6) Uani 1 1 d . . . . .
H16A H 0.0239 0.3509 0.0473 0.063 Uiso 1 1 calc R U . . .
H16B H 0.0223 0.3542 0.2693 0.063 Uiso 1 1 calc R U . . .
C6 C -0.08355(14) 0.27442(13) 0.1882(6) 0.0645(8) Uani 1 1 d . . . . .
H6 H -0.0849 0.3114 0.2000 0.077 Uiso 1 1 calc R U . . .
C4 C -0.08175(18) 0.16474(13) 0.1533(6) 0.0669(8) Uani 1 1 d . . . . .
H4 H -0.0812 0.1277 0.1407 0.080 Uiso 1 1 calc R U . . .
C13 C 0.15903(14) 0.31019(10) 0.1732(7) 0.0534(6) Uani 1 1 d . . . . .
C5 C -0.14490(17) 0.19128(17) 0.1682(8) 0.0799(10) Uani 1 1 d . . . . .
H5 H -0.1870 0.1724 0.1665 0.096 Uiso 1 1 calc R U . . .
C1 C -0.14529(17) 0.24560(17) 0.1854(8) 0.0824(10) Uani 1 1 d . . . . .
H1 H -0.1881 0.2635 0.1954 0.099 Uiso 1 1 calc R U . . .
H3A H 0.1877(18) 0.2144(13) 0.190(7) 0.075(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
O1 C13 1.336(3) . ?
O1 C16 1.440(3) . ?
O3 C8 1.338(3) . ?
O3 H3A 0.91(3) . ?
C9 C8 1.337(3) . ?
C9 C2 1.455(3) . ?
C9 C16 1.494(3) . ?
C8 C13 1.459(3) . ?
O2 C13 1.209(3) . ?
C2 C6 1.393(4) . ?
C2 C3 1.393(3) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 C1 1.376(4) . ?
C6 H6 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C1 1.365(5) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?

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
C13 O1 C16 108.33(19) . . ?
C8 O3 H3A 112(2) . . ?
C8 C9 C2 130.6(2) . . ?
C8 C9 C16 106.5(2) . . ?
C2 C9 C16 122.9(2) . . ?
C9 C8 O3 129.3(2) . . ?
C9 C8 C13 109.6(2) . . ?
O3 C8 C13 121.1(2) . . ?
C6 C2 C3 118.3(2) . . ?
C6 C2 C9 119.6(2) . . ?
C3 C2 C9 122.1(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 C16 C9 106.31(19) . . ?
O1 C16 H16A 110.5 . . ?
C9 C16 H16A 110.5 . . ?
O1 C16 H16B 110.5 . . ?
C9 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C1 C6 C2 120.1(3) . . ?
C1 C6 H6 119.9 . . ?
C2 C6 H6 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O2 C13 O1 121.6(2) . . ?
O2 C13 C8 129.1(2) . . ?
O1 C13 C8 109.3(2) . . ?
C1 C5 C4 119.5(3) . . ?
C1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C1 C6 121.2(3) . . ?
C5 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?

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
C2 C9 C8 O3 -0.1(7) . . . . ?
C16 C9 C8 O3 -179.6(3) . . . . ?
C2 C9 C8 C13 179.4(4) . . . . ?
C16 C9 C8 C13 -0.2(4) . . . . ?
C8 C9 C2 C6 172.3(4) . . . . ?
C16 C9 C2 C6 -8.2(5) . . . . ?
C8 C9 C2 C3 -8.7(6) . . . . ?
C16 C9 C2 C3 170.8(3) . . . . ?
C6 C2 C3 C4 0.7(6) . . . . ?
C9 C2 C3 C4 -178.3(4) . . . . ?
C13 O1 C16 C9 -0.1(4) . . . . ?
C8 C9 C16 O1 0.2(4) . . . . ?
C2 C9 C16 O1 -179.4(3) . . . . ?
C3 C2 C6 C1 -0.3(6) . . . . ?
C9 C2 C6 C1 178.8(4) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C16 O1 C13 O2 -179.3(5) . . . . ?
C16 O1 C13 C8 0.0(4) . . . . ?
C9 C8 C13 O2 179.4(5) . . . . ?
O3 C8 C13 O2 -1.1(7) . . . . ?
C9 C8 C13 O1 0.1(5) . . . . ?
O3 C8 C13 O1 179.6(3) . . . . ?
C3 C4 C5 C1 0.4(8) . . . . ?
C4 C5 C1 C6 0.0(8) . . . . ?
C2 C6 C1 C5 0.0(7) . . . . ?

_refine_diff_density_max         0.127
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_9k
_database_code_depnum_ccdc_archive 'CCDC 1872059'
loop_
_audit_author_name
_audit_author_address
'Eshani Das'
;IIT Kharagpur
India
;
_audit_update_record             
;
2018-10-08 deposited with the CCDC.	2020-04-20 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            'C11 H10 O3'
_chemical_formula_weight         190.19

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'
N N 0.0061 0.0033 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.570(2)
_cell_length_b                   9.753(2)
_cell_length_c                   13.656(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.23(3)
_cell_angle_gamma                90
_cell_volume                     985.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1174
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      26.3

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9887
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12210
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.526
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.917
_reflns_number_total             3610
_reflns_number_gt                1975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.782
_reflns_Friedel_fraction_full    0.825

_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e'
_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)+(0.0652P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 657 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3610
_refine_ls_number_parameters     262
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.003

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
O5 O 0.4484(6) 0.6960(4) 0.6824(3) 0.0706(12) Uani 1 1 d D . . . .
O4 O 0.5439(5) 0.7170(4) 0.9524(3) 0.0661(11) Uani 1 1 d . . . . .
O1 O 0.1606(5) 0.2600(4) 0.5433(3) 0.0667(11) Uani 1 1 d . . . . .
O2 O 0.2454(6) 0.4600(4) 0.6248(3) 0.0741(12) Uani 1 1 d . . . . .
O3 O 0.2164(6) 0.3045(4) 0.8102(3) 0.0698(12) Uani 1 1 d . . . . .
O6 O 0.4400(6) 0.5280(4) 0.8623(3) 0.0761(13) Uani 1 1 d . . . . .
C7 C 0.1336(7) 0.1209(6) 0.6844(4) 0.0497(13) Uani 1 1 d . . . . .
C21 C 0.4980(7) 0.7419(6) 0.7798(4) 0.0509(14) Uani 1 1 d . . . . .
C8 C 0.1864(7) 0.2513(6) 0.7148(4) 0.0501(13) Uani 1 1 d . . . . .
C15 C 0.5970(6) 0.9924(5) 0.7627(4) 0.0480(13) Uani 1 1 d . . . . .
C4 C 0.1008(6) -0.0026(6) 0.7414(4) 0.0481(14) Uani 1 1 d . . . . .
C18 C 0.5627(7) 0.8664(5) 0.8158(4) 0.0471(12) Uani 1 1 d . . . . .
C9 C 0.2046(7) 0.3372(7) 0.6280(4) 0.0580(16) Uani 1 1 d . . . . .
C3 C 0.1313(7) -0.0024(6) 0.8475(4) 0.0579(15) Uani 1 1 d . . . . .
H3 H 0.1715 0.0771 0.8829 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6661(7) 1.2400(6) 0.6620(4) 0.0616(15) Uani 1 1 d . . . . .
C16 C 0.5915(7) 0.9942(6) 0.6587(4) 0.0605(15) Uani 1 1 d . . . . .
H16 H 0.5662 0.9139 0.6216 0.073 Uiso 1 1 calc R U . . .
C14 C 0.6364(7) 1.1186(6) 0.8155(4) 0.0590(14) Uani 1 1 d . . . . .
H14 H 0.6396 1.1212 0.8839 0.071 Uiso 1 1 calc R U . . .
C10 C 0.1135(8) 0.1191(6) 0.5711(4) 0.0644(16) Uani 1 1 d . . . . .
H10A H 0.1945 0.0522 0.5518 0.077 Uiso 1 1 calc R U . . .
H10B H -0.0096 0.0963 0.5383 0.077 Uiso 1 1 calc R U . . .
C19 C 0.5942(8) 0.8574(6) 0.9281(4) 0.0567(14) Uani 1 1 d . . . . .
H19A H 0.7202 0.8751 0.9579 0.068 Uiso 1 1 calc R U . . .
H19B H 0.5206 0.9244 0.9536 0.068 Uiso 1 1 calc R U . . .
C20 C 0.4873(8) 0.6498(7) 0.8640(4) 0.0579(15) Uani 1 1 d . . . . .
C13 C 0.6706(8) 1.2390(6) 0.7662(4) 0.0659(16) Uani 1 1 d . . . . .
H13 H 0.6968 1.3196 0.8027 0.079 Uiso 1 1 calc R U . . .
C17 C 0.6240(8) 1.1166(7) 0.6105(4) 0.0665(17) Uani 1 1 d . . . . .
H17 H 0.6172 1.1150 0.5417 0.080 Uiso 1 1 calc R U . . .
C1 C 0.0378(7) -0.2435(6) 0.8488(4) 0.0593(15) Uani 1 1 d . . . . .
C5 C 0.0387(8) -0.1240(6) 0.6926(4) 0.0652(16) Uani 1 1 d . . . . .
H5 H 0.0156 -0.1262 0.6229 0.078 Uiso 1 1 calc R U . . .
C2 C 0.1011(8) -0.1217(6) 0.8997(4) 0.0644(16) Uani 1 1 d . . . . .
H2 H 0.1235 -0.1200 0.9693 0.077 Uiso 1 1 calc R U . . .
C6 C 0.0094(8) -0.2433(7) 0.7445(5) 0.0701(17) Uani 1 1 d . . . . .
H6 H -0.0293 -0.3229 0.7089 0.084 Uiso 1 1 calc R U . . .
C11 C 0.0023(9) -0.3737(7) 0.9056(5) 0.084(2) Uani 1 1 d . . . . .
H11A H 0.0287 -0.3556 0.9763 0.126 Uiso 1 1 calc R U . . .
H11B H -0.1222 -0.4000 0.8845 0.126 Uiso 1 1 calc R U . . .
H11C H 0.0783 -0.4467 0.8914 0.126 Uiso 1 1 calc R U . . .
C22 C 0.7043(9) 1.3727(7) 0.6086(5) 0.091(2) Uani 1 1 d . . . . .
H22A H 0.7304 1.4459 0.6565 0.136 Uiso 1 1 calc R U . . .
H22B H 0.8062 1.3586 0.5782 0.136 Uiso 1 1 calc R U . . .
H22C H 0.6002 1.3961 0.5579 0.136 Uiso 1 1 calc R U . . .
H3A H 0.303(8) 0.384(7) 0.822(4) 0.09(2) Uiso 1 1 d . . . . .
H5A H 0.40(2) 0.619(10) 0.698(11) 0.40(10) Uiso 1 1 d 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
O5 C21 1.377(6) . ?
O5 H5A 0.893(14) . ?
O4 C20 1.361(6) . ?
O4 C19 1.478(6) . ?
O1 C9 1.361(7) . ?
O1 C10 1.490(7) . ?
O2 C9 1.240(7) . ?
O3 C8 1.375(6) . ?
O3 H3A 1.01(6) . ?
O6 C20 1.239(7) . ?
C7 C8 1.371(8) . ?
C7 C4 1.483(7) . ?
C7 C10 1.522(7) . ?
C21 C18 1.362(8) . ?
C21 C20 1.476(8) . ?
C8 C9 1.481(8) . ?
C15 C16 1.413(7) . ?
C15 C14 1.425(7) . ?
C15 C18 1.478(7) . ?
C4 C5 1.391(8) . ?
C4 C3 1.419(7) . ?
C18 C19 1.503(7) . ?
C3 C2 1.408(8) . ?
C3 H3 0.9300 . ?
C12 C17 1.397(8) . ?
C12 C13 1.416(8) . ?
C12 C22 1.543(8) . ?
C16 C17 1.409(8) . ?
C16 H16 0.9300 . ?
C14 C13 1.405(8) . ?
C14 H14 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?
C1 C6 1.395(8) . ?
C1 C2 1.408(8) . ?
C1 C11 1.541(8) . ?
C5 C6 1.405(8) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C21 O5 H5A 95(10) . . ?
C20 O4 C19 107.1(4) . . ?
C9 O1 C10 108.8(4) . . ?
C8 O3 H3A 115(3) . . ?
C8 C7 C4 131.7(5) . . ?
C8 C7 C10 106.2(5) . . ?
C4 C7 C10 122.1(5) . . ?
C18 C21 O5 130.0(5) . . ?
C18 C21 C20 109.6(4) . . ?
O5 C21 C20 120.4(5) . . ?
C7 C8 O3 128.0(5) . . ?
C7 C8 C9 110.7(5) . . ?
O3 C8 C9 121.3(5) . . ?
C16 C15 C14 117.2(5) . . ?
C16 C15 C18 122.2(5) . . ?
C14 C15 C18 120.6(4) . . ?
C5 C4 C3 117.2(5) . . ?
C5 C4 C7 121.1(5) . . ?
C3 C4 C7 121.7(5) . . ?
C21 C18 C15 130.6(4) . . ?
C21 C18 C19 106.5(5) . . ?
C15 C18 C19 122.8(5) . . ?
O2 C9 O1 121.4(5) . . ?
O2 C9 C8 129.9(5) . . ?
O1 C9 C8 108.7(5) . . ?
C2 C3 C4 120.4(5) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C17 C12 C13 117.0(5) . . ?
C17 C12 C22 122.0(6) . . ?
C13 C12 C22 120.9(6) . . ?
C17 C16 C15 120.6(6) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C13 C14 C15 121.3(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
O1 C10 C7 105.7(5) . . ?
O1 C10 H10A 110.6 . . ?
C7 C10 H10A 110.6 . . ?
O1 C10 H10B 110.6 . . ?
C7 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
O4 C19 C18 106.9(4) . . ?
O4 C19 H19A 110.3 . . ?
C18 C19 H19A 110.3 . . ?
O4 C19 H19B 110.3 . . ?
C18 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
O6 C20 O4 121.0(5) . . ?
O6 C20 C21 129.2(5) . . ?
O4 C20 C21 109.8(5) . . ?
C14 C13 C12 121.3(6) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C12 C17 C16 122.6(5) . . ?
C12 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C6 C1 C2 117.7(6) . . ?
C6 C1 C11 120.7(6) . . ?
C2 C1 C11 121.7(6) . . ?
C4 C5 C6 122.5(5) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C1 C6 C5 120.7(6) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_9q
_database_code_depnum_ccdc_archive 'CCDC 1872060'
loop_
_audit_author_name
_audit_author_address
'Eshani Das'
;IIT Kharagpur
India
;
_audit_update_record             
;
2018-10-08 deposited with the CCDC.	2020-04-20 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            'C80 H56 N8 O40'
_chemical_formula_weight         1769.32

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'
N N 0.0061 0.0033 '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                   25.689(5)
_cell_length_b                   10.003(2)
_cell_length_c                   7.418(2)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 105.62(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1835.8(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    450
_cell_measurement_theta_min      1.646
_cell_measurement_theta_max      26.44

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11385
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.646
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1880
_reflns_number_gt                1152
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e'
_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)+(0.0722P)²] 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         1880
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
O3 O 0.62508(6) 0.01220(15) 0.3700(2) 0.0549(5) Uani 1 1 d . . . . .
O4 O 0.52540(6) 0.21708(18) 0.4799(3) 0.0577(5) Uani 1 1 d . . . . .
O5 O 0.55212(7) -0.06482(16) 0.4444(3) 0.0647(6) Uani 1 1 d . . . . .
N1 N 0.72433(8) 0.6177(2) 0.3221(3) 0.0539(6) Uani 1 1 d . . . . .
O2 O 0.72775(8) 0.73532(19) 0.2816(3) 0.0753(6) Uani 1 1 d . . . . .
O1 O 0.76073(7) 0.5382(2) 0.3357(3) 0.0867(7) Uani 1 1 d . . . . .
C5 C 0.61784(8) 0.3852(2) 0.3866(3) 0.0384(5) Uani 1 1 d . . . . .
C7 C 0.60922(8) 0.2415(2) 0.3934(3) 0.0399(6) Uani 1 1 d . . . . .
C6 C 0.66593(8) 0.4341(2) 0.3606(3) 0.0423(5) Uani 1 1 d . . . . .
H6 H 0.6929 0.3754 0.3483 0.051 Uiso 1 1 calc R U . . .
C9 C 0.56924(9) 0.1719(2) 0.4336(3) 0.0426(6) Uani 1 1 d . . . . .
C10 C 0.57904(9) 0.0293(2) 0.4193(3) 0.0466(6) Uani 1 1 d . . . . .
C1 C 0.67338(9) 0.5704(2) 0.3531(3) 0.0436(6) Uani 1 1 d . . . . .
C4 C 0.57830(9) 0.4773(2) 0.4026(3) 0.0464(6) Uani 1 1 d . . . . .
H4 H 0.5458 0.4464 0.4195 0.056 Uiso 1 1 calc R U . . .
C2 C 0.63495(10) 0.6611(2) 0.3685(3) 0.0496(6) Uani 1 1 d . . . . .
H2 H 0.6409 0.7525 0.3623 0.060 Uiso 1 1 calc R U . . .
C3 C 0.58679(10) 0.6125(2) 0.3938(3) 0.0524(6) Uani 1 1 d . . . . .
H3 H 0.5600 0.6720 0.4049 0.063 Uiso 1 1 calc R U . . .
C8 C 0.64816(9) 0.1424(2) 0.3525(4) 0.0500(6) Uani 1 1 d . . . . .
H8A H 0.6520 0.1551 0.2271 0.060 Uiso 1 1 calc R U . . .
H8B H 0.6834 0.1515 0.4413 0.060 Uiso 1 1 calc R U . . .
H4A H 0.5053(13) 0.142(3) 0.499(4) 0.108(12) 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
O3 C10 1.339(3) . ?
O3 C8 1.451(3) . ?
O4 C9 1.342(3) . ?
O4 H4A 0.94(3) . ?
O5 C10 1.212(3) . ?
N1 O1 1.211(3) . ?
N1 O2 1.223(3) . ?
N1 C1 1.467(3) . ?
C5 C6 1.389(3) . ?
C5 C4 1.399(3) . ?
C5 C7 1.458(3) . ?
C7 C9 1.339(3) . ?
C7 C8 1.496(3) . ?
C6 C1 1.381(3) . ?
C6 H6 0.9300 . ?
C9 C10 1.457(3) . ?
C1 C2 1.367(3) . ?
C4 C3 1.375(3) . ?
C4 H4 0.9300 . ?
C2 C3 1.388(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 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
C10 O3 C8 108.79(17) . . ?
C9 O4 H4A 108(2) . . ?
O1 N1 O2 123.2(2) . . ?
O1 N1 C1 118.5(2) . . ?
O2 N1 C1 118.3(2) . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 C7 120.04(19) . . ?
C4 C5 C7 121.68(19) . . ?
C9 C7 C5 130.81(19) . . ?
C9 C7 C8 107.17(19) . . ?
C5 C7 C8 122.02(18) . . ?
C1 C6 C5 119.4(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C7 C9 O4 128.9(2) . . ?
C7 C9 C10 109.6(2) . . ?
O4 C9 C10 121.5(2) . . ?
O5 C10 O3 121.7(2) . . ?
O5 C10 C9 129.2(2) . . ?
O3 C10 C9 109.1(2) . . ?
C2 C1 C6 122.7(2) . . ?
C2 C1 N1 119.6(2) . . ?
C6 C1 N1 117.6(2) . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O3 C8 C7 105.35(17) . . ?
O3 C8 H8A 110.7 . . ?
C7 C8 H8A 110.7 . . ?
O3 C8 H8B 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_9t
_database_code_depnum_ccdc_archive 'CCDC 1872061'
loop_
_audit_author_name
_audit_author_address
'Eshani Das'
;IIT Kharagpur
India
;
_audit_update_record             
;
2018-10-08 deposited with the CCDC.	2020-04-20 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            'C22 H14 N2 O6'
_chemical_formula_weight         402.35

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'
N N 0.0061 0.0033 '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                   8.009
_cell_length_b                   9.607
_cell_length_c                   13.044
_cell_angle_alpha                94.77
_cell_angle_beta                 105.91
_cell_angle_gamma                108.25
_cell_volume                     900.8
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    350
_cell_measurement_theta_min      2.824
_cell_measurement_theta_max      26.609

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8034
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         26.609
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3650
_reflns_number_gt                2118
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2.1e'
_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)+(0.1120P)²+0.5161P] 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         3650
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2304
_refine_ls_wR_factor_gt          0.1975
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O3 O 0.2808(3) 0.5808(3) -0.0600(2) 0.0601(8) Uani 1 1 d . . . . .
H3A H 0.1960 0.5034 -0.0646 0.090 Uiso 1 1 calc R U . . .
O6 O 0.9215(3) 0.7340(3) 0.4426(2) 0.0603(8) Uani 1 1 d . . . . .
H6A H 0.9925 0.8148 0.4391 0.090 Uiso 1 1 calc R U . . .
O4 O 1.1741(4) 0.7484(3) 0.7165(2) 0.0628(8) Uani 1 1 d . . . . .
O1 O 0.5213(4) 0.5928(3) 0.2158(2) 0.0644(8) Uani 1 1 d . . . . .
O5 O 1.2526(4) 0.9238(3) 0.6204(2) 0.0700(9) Uani 1 1 d . . . . .
O2 O 0.2548(4) 0.4143(3) 0.1178(2) 0.0689(9) Uani 1 1 d . . . . .
C15 C 0.7388(4) 0.4537(3) 0.5314(3) 0.0391(8) Uani 1 1 d . . . . .
N1 N 0.9530(5) 1.3232(3) -0.1367(3) 0.0630(9) Uani 1 1 d . . . . .
N2 N 0.1207(5) -0.0233(4) 0.3592(3) 0.0666(10) Uani 1 1 d . . . . .
C7 C 0.8833(5) 1.2223(4) -0.1044(3) 0.0441(8) Uani 1 1 d . . . . .
C8 C 0.5603(5) 0.7357(3) 0.0823(3) 0.0421(8) Uani 1 1 d . . . . .
C1 C 0.8028(5) 1.0985(3) -0.0568(3) 0.0422(8) Uani 1 1 d . . . . .
C4 C 0.6438(5) 0.8599(3) 0.0306(3) 0.0391(8) Uani 1 1 d . . . . .
C11 C 0.4035(5) 0.6189(3) 0.0404(3) 0.0431(8) Uani 1 1 d . . . . .
C21 C 0.9792(5) 0.7032(4) 0.5418(3) 0.0433(8) Uani 1 1 d . . . . .
C22 C 1.1498(5) 0.8062(4) 0.6268(3) 0.0471(9) Uani 1 1 d . . . . .
C3 C 0.8051(5) 0.9747(4) 0.0943(3) 0.0470(9) Uani 1 1 d . . . . .
H3 H 0.8599 0.9713 0.1664 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4207(4) 0.2052(4) 0.4417(3) 0.0451(9) Uani 1 1 d . . . . .
C16 C 0.6271(5) 0.4396(4) 0.4259(3) 0.0458(9) Uani 1 1 d . . . . .
H16 H 0.6595 0.5142 0.3864 0.055 Uiso 1 1 calc R U . . .
C19 C 0.9069(5) 0.5858(4) 0.5825(3) 0.0431(8) Uani 1 1 d . . . . .
C10 C 0.3774(5) 0.5272(4) 0.1241(3) 0.0475(9) Uani 1 1 d . . . . .
C18 C 0.2520(5) 0.0787(4) 0.3920(3) 0.0461(9) Uani 1 1 d . . . . .
C5 C 0.5633(5) 0.8642(4) -0.0763(3) 0.0455(9) Uani 1 1 d . . . . .
H5 H 0.4562 0.7866 -0.1183 0.055 Uiso 1 1 calc R U . . .
C17 C 0.4678(5) 0.3152(4) 0.3790(3) 0.0466(9) Uani 1 1 d . . . . .
H17 H 0.3938 0.3047 0.3080 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6410(5) 0.9834(4) -0.1216(3) 0.0486(9) Uani 1 1 d . . . . .
H6 H 0.5869 0.9870 -0.1937 0.058 Uiso 1 1 calc R U . . .
C13 C 0.5294(5) 0.2182(4) 0.5444(3) 0.0500(9) Uani 1 1 d . . . . .
H13 H 0.4961 0.1442 0.5842 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8827(5) 1.0941(4) 0.0489(3) 0.0493(9) Uani 1 1 d . . . . .
H2 H 0.9899 1.1716 0.0908 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6909(5) 0.3420(4) 0.5907(3) 0.0493(9) Uani 1 1 d . . . . .
H14 H 0.7664 0.3500 0.6609 0.059 Uiso 1 1 calc R U . . .
C20 C 1.0273(5) 0.6049(4) 0.6966(3) 0.0560(10) Uani 1 1 d . . . . .
H20A H 0.9575 0.6042 0.7467 0.067 Uiso 1 1 calc R U . . .
H20B H 1.0781 0.5256 0.7045 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6448(6) 0.7267(4) 0.1967(3) 0.0556(10) Uani 1 1 d . . . . .
H9A H 0.7671 0.7208 0.2080 0.067 Uiso 1 1 calc R U . . .
H9B H 0.6558 0.8135 0.2453 0.067 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
O3 C11 1.344(4) . ?
O3 H3A 0.8200 . ?
O6 C21 1.341(4) . ?
O6 H6A 0.8200 . ?
O4 C22 1.329(4) . ?
O4 C20 1.452(4) . ?
O1 C10 1.349(5) . ?
O1 C9 1.444(4) . ?
O5 C22 1.197(4) . ?
O2 C10 1.193(4) . ?
C15 C16 1.389(5) . ?
C15 C14 1.393(5) . ?
C15 C19 1.472(5) . ?
N1 C7 1.134(4) . ?
N2 C18 1.135(4) . ?
C7 C1 1.442(4) . ?
C8 C11 1.332(5) . ?
C8 C9 1.482(5) . ?
C8 C4 1.486(4) . ?
C1 C2 1.361(5) . ?
C1 C6 1.401(5) . ?
C4 C5 1.377(5) . ?
C4 C3 1.394(5) . ?
C11 C10 1.476(5) . ?
C21 C19 1.322(5) . ?
C21 C22 1.488(5) . ?
C3 C2 1.386(5) . ?
C3 H3 0.9300 . ?
C12 C13 1.354(5) . ?
C12 C17 1.412(5) . ?
C12 C18 1.443(5) . ?
C16 C17 1.388(5) . ?
C16 H16 0.9300 . ?
C19 C20 1.495(5) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C6 H6 0.9300 . ?
C13 C14 1.393(5) . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C14 H14 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 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
C11 O3 H3A 109.5 . . ?
C21 O6 H6A 109.5 . . ?
C22 O4 C20 108.9(3) . . ?
C10 O1 C9 109.0(3) . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 C19 121.1(3) . . ?
C14 C15 C19 119.0(3) . . ?
N1 C7 C1 176.4(4) . . ?
C11 C8 C9 108.1(3) . . ?
C11 C8 C4 129.0(3) . . ?
C9 C8 C4 122.8(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 C7 120.5(3) . . ?
C6 C1 C7 118.5(3) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 C8 121.5(3) . . ?
C3 C4 C8 118.0(3) . . ?
C8 C11 O3 129.3(3) . . ?
C8 C11 C10 109.0(3) . . ?
O3 C11 C10 121.7(3) . . ?
C19 C21 O6 129.8(3) . . ?
C19 C21 C22 108.3(3) . . ?
O6 C21 C22 121.8(3) . . ?
O5 C22 O4 122.9(3) . . ?
O5 C22 C21 127.9(4) . . ?
O4 C22 C21 109.1(3) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C13 C12 C17 121.2(3) . . ?
C13 C12 C18 121.5(3) . . ?
C17 C12 C18 117.3(3) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C21 C19 C15 129.4(3) . . ?
C21 C19 C20 108.4(3) . . ?
C15 C19 C20 122.2(3) . . ?
O2 C10 O1 122.6(3) . . ?
O2 C10 C11 129.1(4) . . ?
O1 C10 C11 108.2(3) . . ?
N2 C18 C12 175.7(4) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C16 C17 C12 118.4(4) . . ?
C16 C17 H17 120.8 . . ?
C12 C17 H17 120.8 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O4 C20 C19 105.2(3) . . ?
O4 C20 H20A 110.7 . . ?
C19 C20 H20A 110.7 . . ?
O4 C20 H20B 110.7 . . ?
C19 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
O1 C9 C8 105.7(3) . . ?
O1 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
O1 C9 H9B 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.063

