# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_3ba
_database_code_depnum_ccdc_archive 'CCDC 2169711'
loop_
_audit_author_name
_audit_author_address
'Sanjay Mandal'
;IISER Mohali
India
;
_audit_update_record             
;
2022-04-30 deposited with the CCDC.	2022-05-11 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         'C21 H14 N2 O4'
_chemical_formula_sum            'C21 H14 N2 O4'
_chemical_formula_weight         358.34

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'
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                   10.8392(10)
_cell_length_b                   6.9083(6)
_cell_length_c                   13.2119(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.035(3)
_cell_angle_gamma                90
_cell_volume                     940.71(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24163
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.919
_diffrn_reflns_theta_max         25.108
_diffrn_reflns_theta_full        25.108
_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 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3319
_reflns_number_gt                2765
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.02(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   4(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     247
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1613
_refine_ls_R_factor_gt           0.1454
_refine_ls_wR_factor_ref         0.4103
_refine_ls_wR_factor_gt          0.3853
_refine_ls_goodness_of_fit_ref   1.706
_refine_ls_restrained_S_all      1.705
_refine_ls_shift/su_max          0.001
_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
N001 N 0.7084(8) 0.2637(15) 0.1830(6) 0.058(3) Uani 1 1 d . . . . .
C002 C 0.5243(8) 0.2614(12) 0.0279(7) 0.042(2) Uani 1 1 d . . . . .
C003 C 0.5757(8) 0.2472(13) 0.1424(8) 0.040(2) Uani 1 1 d . . . . .
O004 O 0.5141(7) 0.2537(12) 0.2038(7) 0.063(2) Uani 1 1 d . . . . .
C005 C 0.7881(9) 0.2579(17) 0.2878(7) 0.051(3) Uani 1 1 d . . . . .
C006 C 0.6073(9) 0.2538(17) -0.0390(8) 0.057(3) Uani 1 1 d . . . . .
C007 C 0.9187(8) 0.2557(14) 0.2935(7) 0.043(2) Uani 1 1 d . . . . .
C008 C 1.0171(9) 0.2526(15) 0.3893(7) 0.044(2) Uani 1 1 d . . . . .
H008 H 1.103554 0.251266 0.391060 0.052 Uiso 1 1 calc R U . . .
C009 C 0.3930(10) 0.2451(18) -0.0222(12) 0.071(4) Uani 1 1 d . . . . .
H009 H 0.337944 0.221694 0.018282 0.085 Uiso 1 1 calc R U . . .
O010 O 0.8252(8) 0.249(4) -0.0404(7) 0.173(10) Uani 1 1 d . . . . .
C011 C 0.3406(10) 0.263(2) -0.1327(11) 0.070(4) Uani 1 1 d . . . . .
H011 H 0.251487 0.274602 -0.164839 0.084 Uiso 1 1 calc R U . . .
C012 C 0.4230(11) 0.2629(18) -0.1920(10) 0.068(4) Uani 1 1 d . . . . .
H012 H 0.389499 0.257861 -0.265836 0.081 Uiso 1 1 calc R U . . .
C013 C 0.8562(12) 0.2649(15) 0.4784(7) 0.055(3) Uani 1 1 d . . . . .
H013 H 0.835806 0.274477 0.541595 0.066 Uiso 1 1 calc R U . . .
C014 C 0.9844(12) 0.2515(17) 0.4836(7) 0.057(3) Uani 1 1 d . . . . .
N015 N 0.7917(8) 0.245(3) 0.1173(7) 0.113(7) Uani 1 1 d . . . . .
C016 C 0.7446(9) 0.282(3) 0.0111(8) 0.083(5) Uani 1 1 d . . . . .
C017 C 0.5534(11) 0.270(2) -0.1455(10) 0.065(3) Uani 1 1 d . . . . .
H017 H 0.606884 0.286548 -0.187861 0.078 Uiso 1 1 calc R U . . .
C018 C 0.7545(11) 0.2649(17) 0.3818(8) 0.055(3) Uani 1 1 d . . . . .
H018 H 0.668242 0.269342 0.380381 0.066 Uiso 1 1 calc R U . . .
C020 C 1.0966(13) 0.2386(16) 0.5907(8) 0.066(3) Uani 1 1 d . . . . .
H02A H 1.108199 0.106289 0.613959 0.099 Uiso 1 1 calc R U . . .
H02B H 1.075541 0.315798 0.643468 0.099 Uiso 1 1 calc R U . . .
H02C H 1.175335 0.285707 0.580662 0.099 Uiso 1 1 calc R U . . .
C2 C 0.9267(9) 0.250(3) 0.1810(8) 0.085(5) Uani 1 1 d D . . . .
C1 C 0.9862(12) 0.040(3) 0.1537(10) 0.095(6) Uani 1 1 d D . . . .
H1A H 0.951850 -0.067829 0.183516 0.115 Uiso 1 1 calc R U . . .
H1B H 0.965430 0.021622 0.077503 0.115 Uiso 1 1 calc R U . . .
C5 C 1.0004(14) 0.423(4) 0.1550(17) 0.153(13) Uani 1 1 d D . . . .
C10 C 1.1434(12) 0.061(3) 0.2101(12) 0.088(5) Uani 1 1 d D . . . .
O2 O 0.9320(13) 0.524(2) 0.1165(13) 0.120(5) Uani 1 1 d . . . . .
O1 O 1.2068(13) -0.076(2) 0.2761(8) 0.110(4) Uani 1 1 d . . . . .
C3 C 1.2047(12) 0.248(3) 0.1963(11) 0.088(6) Uani 1 1 d . . . . .
H3 H 1.294119 0.265362 0.218557 0.105 Uiso 1 1 calc R U . . .
C4 C 1.1376(17) 0.362(3) 0.1585(13) 0.092(6) Uani 1 1 d . . . . .
H4 H 1.171939 0.442974 0.117897 0.111 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
N001 C003 1.376(11) . ?
N001 C005 1.387(12) . ?
N001 N015 1.440(12) . ?
C002 C009 1.376(15) . ?
C002 C006 1.444(14) . ?
C002 C003 1.445(14) . ?
C003 O004 1.200(11) . ?
C005 C007 1.394(13) . ?
C005 C018 1.399(13) . ?
C006 C017 1.351(16) . ?
C006 C016 1.441(14) . ?
C007 C008 1.380(13) . ?
C007 C2 1.517(13) . ?
C008 C014 1.398(13) . ?
C008 H008 0.9300 . ?
C009 C011 1.40(2) . ?
C009 H009 0.9300 . ?
O010 C016 1.282(14) . ?
C011 C012 1.359(18) . ?
C011 H011 0.9300 . ?
C012 C017 1.356(16) . ?
C012 H012 0.9300 . ?
C013 C014 1.372(17) . ?
C013 C018 1.405(16) . ?
C013 H013 0.9300 . ?
C014 C020 1.557(16) . ?
N015 C016 1.361(14) . ?
N015 C2 1.445(12) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C020 H02A 0.9600 . ?
C020 H02B 0.9600 . ?
C020 H02C 0.9600 . ?
C2 C5 1.54(3) . ?
C2 C1 1.67(3) . ?
C1 C10 1.64(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 O2 1.03(2) . ?
C5 C4 1.53(3) . ?
C10 O1 1.32(2) . ?
C10 C3 1.49(3) . ?
C3 C4 1.08(2) . ?
C3 H3 0.9300 . ?
C4 H4 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
C003 N001 C005 129.8(8) . . ?
C003 N001 N015 122.2(8) . . ?
C005 N001 N015 106.6(7) . . ?
C009 C002 C006 116.8(10) . . ?
C009 C002 C003 120.3(9) . . ?
C006 C002 C003 121.8(8) . . ?
O004 C003 N001 117.8(9) . . ?
O004 C003 C002 126.1(8) . . ?
N001 C003 C002 114.9(7) . . ?
N001 C005 C007 111.3(8) . . ?
N001 C005 C018 129.2(9) . . ?
C007 C005 C018 119.4(9) . . ?
C017 C006 C016 121.3(10) . . ?
C017 C006 C002 118.9(9) . . ?
C016 C006 C002 117.7(10) . . ?
C008 C007 C005 122.3(8) . . ?
C008 C007 C2 129.5(8) . . ?
C005 C007 C2 108.2(8) . . ?
C007 C008 C014 118.7(8) . . ?
C007 C008 H008 120.7 . . ?
C014 C008 H008 120.7 . . ?
C002 C009 C011 121.3(11) . . ?
C002 C009 H009 119.3 . . ?
C011 C009 H009 119.3 . . ?
C012 C011 C009 118.3(9) . . ?
C012 C011 H011 120.8 . . ?
C009 C011 H011 120.8 . . ?
C017 C012 C011 121.2(12) . . ?
C017 C012 H012 119.4 . . ?
C011 C012 H012 119.4 . . ?
C014 C013 C018 122.9(8) . . ?
C014 C013 H013 118.5 . . ?
C018 C013 H013 118.5 . . ?
C013 C014 C008 119.2(9) . . ?
C013 C014 C020 123.0(9) . . ?
C008 C014 C020 117.9(10) . . ?
C016 N015 N001 119.9(10) . . ?
C016 N015 C2 125.8(8) . . ?
N001 N015 C2 110.9(8) . . ?
O010 C016 N015 114.4(12) . . ?
O010 C016 C006 120.6(11) . . ?
N015 C016 C006 116.9(9) . . ?
C006 C017 C012 121.6(11) . . ?
C006 C017 H017 119.2 . . ?
C012 C017 H017 119.2 . . ?
C005 C018 C013 117.4(9) . . ?
C005 C018 H018 121.3 . . ?
C013 C018 H018 121.3 . . ?
C014 C020 H02A 109.5 . . ?
C014 C020 H02B 109.5 . . ?
H02A C020 H02B 109.5 . . ?
C014 C020 H02C 109.5 . . ?
H02A C020 H02C 109.5 . . ?
H02B C020 H02C 109.5 . . ?
N015 C2 C007 102.5(8) . . ?
N015 C2 C5 113.1(14) . . ?
C007 C2 C5 112.9(16) . . ?
N015 C2 C1 104.0(14) . . ?
C007 C2 C1 112.2(12) . . ?
C5 C2 C1 111.5(13) . . ?
C10 C1 C2 104.1(13) . . ?
C10 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
C10 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 109.0 . . ?
O2 C5 C4 138.3(17) . . ?
O2 C5 C2 107.0(14) . . ?
C4 C5 C2 110.0(19) . . ?
O1 C10 C3 122.6(13) . . ?
O1 C10 C1 119.4(16) . . ?
C3 C10 C1 117.3(15) . . ?
C4 C3 C10 115.2(14) . . ?
C4 C3 H3 122.4 . . ?
C10 C3 H3 122.4 . . ?
C3 C4 C5 136.2(19) . . ?
C3 C4 H4 111.9 . . ?
C5 C4 H4 111.9 . . ?

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
C005 N001 C003 O004 11.1(18) . . . . ?
N015 N001 C003 O004 175.7(12) . . . . ?
C005 N001 C003 C002 179.6(10) . . . . ?
N015 N001 C003 C002 -15.8(17) . . . . ?
C009 C002 C003 O004 -13.3(15) . . . . ?
C006 C002 C003 O004 179.4(10) . . . . ?
C009 C002 C003 N001 179.3(10) . . . . ?
C006 C002 C003 N001 12.0(13) . . . . ?
C003 N001 C005 C007 172.4(11) . . . . ?
N015 N001 C005 C007 6.0(15) . . . . ?
C003 N001 C005 C018 -11(2) . . . . ?
N015 N001 C005 C018 -177.9(13) . . . . ?
C009 C002 C006 C017 13.0(16) . . . . ?
C003 C002 C006 C017 -179.3(10) . . . . ?
C009 C002 C006 C016 176.5(12) . . . . ?
C003 C002 C006 C016 -15.7(16) . . . . ?
N001 C005 C007 C008 179.1(9) . . . . ?
C018 C005 C007 C008 2.6(16) . . . . ?
N001 C005 C007 C2 -2.9(15) . . . . ?
C018 C005 C007 C2 -179.5(11) . . . . ?
C005 C007 C008 C014 0.1(16) . . . . ?
C2 C007 C008 C014 -177.4(13) . . . . ?
C006 C002 C009 C011 -13.6(16) . . . . ?
C003 C002 C009 C011 178.5(11) . . . . ?
C002 C009 C011 C012 11(2) . . . . ?
C009 C011 C012 C017 -8(2) . . . . ?
C018 C013 C014 C008 5.1(17) . . . . ?
C018 C013 C014 C020 -176.1(10) . . . . ?
C007 C008 C014 C013 -3.8(16) . . . . ?
C007 C008 C014 C020 177.3(9) . . . . ?
C003 N001 N015 C016 25(2) . . . . ?
C005 N001 N015 C016 -167.5(16) . . . . ?
C003 N001 N015 C2 -174.6(14) . . . . ?
C005 N001 N015 C2 -6.9(19) . . . . ?
N001 N015 C016 O010 -176.2(18) . . . . ?
C2 N015 C016 O010 26(3) . . . . ?
N001 N015 C016 C006 -27(3) . . . . ?
C2 N015 C016 C006 175.3(19) . . . . ?
C017 C006 C016 O010 -27(3) . . . . ?
C002 C006 C016 O010 169.9(18) . . . . ?
C017 C006 C016 N015 -174.0(17) . . . . ?
C002 C006 C016 N015 23(2) . . . . ?
C016 C006 C017 C012 -173.4(15) . . . . ?
C002 C006 C017 C012 -10.5(19) . . . . ?
C011 C012 C017 C006 8(2) . . . . ?
N001 C005 C018 C013 -177.3(11) . . . . ?
C007 C005 C018 C013 -1.4(16) . . . . ?
C014 C013 C018 C005 -2.4(17) . . . . ?
C016 N015 C2 C007 164(2) . . . . ?
N001 N015 C2 C007 5(2) . . . . ?
C016 N015 C2 C5 42(3) . . . . ?
N001 N015 C2 C5 -116.9(18) . . . . ?
C016 N015 C2 C1 -79(2) . . . . ?
N001 N015 C2 C1 121.9(14) . . . . ?
C008 C007 C2 N015 176.5(13) . . . . ?
C005 C007 C2 N015 -1.3(18) . . . . ?
C008 C007 C2 C5 -61.6(19) . . . . ?
C005 C007 C2 C5 120.7(12) . . . . ?
C008 C007 C2 C1 65.5(17) . . . . ?
C005 C007 C2 C1 -112.3(10) . . . . ?
N015 C2 C1 C10 171.0(10) . . . . ?
C007 C2 C1 C10 -78.9(13) . . . . ?
C5 C2 C1 C10 48.9(13) . . . . ?
N015 C2 C5 O2 19(3) . . . . ?
C007 C2 C5 O2 -97(2) . . . . ?
C1 C2 C5 O2 136(2) . . . . ?
N015 C2 C5 C4 -141.2(15) . . . . ?
C007 C2 C5 C4 102.9(19) . . . . ?
C1 C2 C5 C4 -24.5(18) . . . . ?
C2 C1 C10 O1 127.4(12) . . . . ?
C2 C1 C10 C3 -43.8(14) . . . . ?
O1 C10 C3 C4 -163.2(14) . . . . ?
C1 C10 C3 C4 8(2) . . . . ?
C10 C3 C4 C5 33(3) . . . . ?
O2 C5 C4 C3 -175(3) . . . . ?
C2 C5 C4 C3 -23(3) . . . . ?

_refine_diff_density_max         0.819
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.138



