# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2002889'
loop_
_audit_author_name
_audit_author_address
'Venkatramaiah Nutalapati'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2020-05-09 deposited with the CCDC.	2020-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O5'
_chemical_formula_weight         364.35

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.7009(7)
_cell_length_b                   18.4626(17)
_cell_length_c                   24.055(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3420.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1330
_cell_measurement_theta_min      3.8150
_cell_measurement_theta_max      21.3370

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62997
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13010
_diffrn_reflns_av_unetI/netI     0.1023
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.365
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_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             3897
_reflns_number_gt                1570
_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-2017/1 (Sheldrick, 2017)'
_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)+(0.0588P)²+0.9045P] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3897
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1855
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2150
_refine_ls_wR_factor_gt          0.1528
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C1 C -0.2087(5) 0.1519(2) 0.65608(18) 0.0520(10) Uani 1 1 d . . . . .
C2 C -0.2850(5) 0.0842(2) 0.6465(2) 0.0640(12) Uani 1 1 d . . . . .
H2 H -0.303569 0.066721 0.610730 0.077 Uiso 1 1 calc R U . . .
C3 C -0.3310(5) 0.0451(2) 0.6928(2) 0.0740(14) Uani 1 1 d . . . . .
H3 H -0.382765 0.000068 0.687553 0.089 Uiso 1 1 calc R U . . .
C4 C -0.3049(5) 0.0686(2) 0.7470(2) 0.0664(13) Uani 1 1 d . . . . .
H4 H -0.339313 0.039632 0.776668 0.080 Uiso 1 1 calc R U . . .
C5 C -0.2276(5) 0.1353(2) 0.75705(18) 0.0524(10) Uani 1 1 d . . . . .
C6 C -0.1911(5) 0.1702(2) 0.81087(18) 0.0564(11) Uani 1 1 d . . . . .
C7 C -0.1071(4) 0.2441(2) 0.80893(16) 0.0506(10) Uani 1 1 d . . . . .
C8 C -0.0673(5) 0.2776(2) 0.85885(17) 0.0644(12) Uani 1 1 d . . . . .
H8 H -0.092745 0.254120 0.892076 0.077 Uiso 1 1 calc R U . . .
C9 C 0.0091(6) 0.3450(3) 0.8602(2) 0.0754(13) Uani 1 1 d . . . . .
H9 H 0.035310 0.366355 0.894181 0.090 Uiso 1 1 calc R U . . .
C10 C 0.0469(6) 0.3807(2) 0.81164(19) 0.0677(12) Uani 1 1 d . . . . .
H10 H 0.097628 0.426390 0.812877 0.081 Uiso 1 1 calc R U . . .
C11 C 0.0097(5) 0.3491(2) 0.76083(17) 0.0563(11) Uani 1 1 d . . . . .
H11 H 0.035194 0.373416 0.727992 0.068 Uiso 1 1 calc R U . . .
C12 C -0.0657(4) 0.2809(2) 0.75908(15) 0.0472(9) Uani 1 1 d . . . . .
C13 C -0.1065(4) 0.24357(19) 0.70725(16) 0.0445(9) Uani 1 1 d . . . . .
C14 C -0.1823(4) 0.17472(18) 0.70979(16) 0.0451(9) Uani 1 1 d . . . . .
C15 C -0.1579(5) 0.2137(2) 0.56263(16) 0.0607(11) Uani 1 1 d . . . . .
H15A H -0.181502 0.263735 0.552927 0.073 Uiso 1 1 calc R U . . .
H15B H -0.252720 0.184418 0.548526 0.073 Uiso 1 1 calc R U . . .
C16 C 0.0062(5) 0.1906(2) 0.53525(16) 0.0584(11) Uani 1 1 d . . . . .
H16A H 0.000061 0.199476 0.495553 0.070 Uiso 1 1 calc R U . . .
H16B H 0.103713 0.217560 0.550252 0.070 Uiso 1 1 calc R U . . .
C17 C 0.1741(6) 0.0845(2) 0.5292(2) 0.0648(12) Uani 1 1 d . . . . .
C18 C 0.1888(5) 0.0074(2) 0.5465(2) 0.0791(14) Uani 1 1 d . . . . .
H18A H 0.098181 -0.003046 0.573373 0.095 Uiso 1 1 calc R U . . .
H18B H 0.169540 -0.023260 0.514395 0.095 Uiso 1 1 calc R U . . .
C19 C 0.3533(6) -0.0103(2) 0.5705(2) 0.0907(16) Uani 1 1 d . . . . .
H19A H 0.361097 0.013116 0.606525 0.109 Uiso 1 1 calc R U . . .
H19B H 0.443623 0.010116 0.547197 0.109 Uiso 1 1 calc R U . . .
C20 C 0.3905(6) -0.0899(2) 0.5782(2) 0.0633(12) Uani 1 1 d . . . . .
N1 N -0.0892(4) 0.26308(15) 0.65433(13) 0.0496(8) Uani 1 1 d . . . . .
N2 N -0.1519(4) 0.20708(16) 0.62294(13) 0.0521(8) Uani 1 1 d . . . . .
O1 O -0.2264(4) 0.14170(17) 0.85514(13) 0.0862(10) Uani 1 1 d . . . . .
O2 O 0.0273(3) 0.11432(13) 0.54602(11) 0.0598(8) Uani 1 1 d . . . . .
O4 O 0.5001(4) -0.10045(15) 0.61922(13) 0.0823(10) Uani 1 1 d . . . . .
H4A H 0.519381 -0.143928 0.622468 0.123 Uiso 1 1 calc R U . . .
O5 O 0.3284(4) -0.13780(16) 0.55155(13) 0.0735(9) Uani 1 1 d . . . . .
O3A O 0.2569(13) 0.1094(5) 0.4934(5) 0.065(3) Uiso 0.49(3) 1 d . . P A 1
O3B O 0.3035(14) 0.1232(5) 0.5129(5) 0.068(3) Uiso 0.51(3) 1 d . . P A 1


_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
C1 N2 1.366(5) . ?
C1 C14 1.374(5) . ?
C1 C2 1.400(5) . ?
C2 C3 1.375(6) . ?
C3 C4 1.389(6) . ?
C4 C5 1.389(5) . ?
C5 C14 1.394(5) . ?
C5 C6 1.473(6) . ?
C6 O1 1.218(4) . ?
C6 C7 1.512(5) . ?
C7 C8 1.385(5) . ?
C7 C12 1.415(5) . ?
C8 C9 1.376(6) . ?
C9 C10 1.373(6) . ?
C10 C11 1.385(5) . ?
C11 C12 1.386(5) . ?
C12 C13 1.459(5) . ?
C13 N1 1.330(4) . ?
C13 C14 1.400(5) . ?
C15 N2 1.457(5) . ?
C15 C16 1.487(5) . ?
C16 O2 1.442(4) . ?
C17 O3A 1.165(7) . ?
C17 O3B 1.287(10) . ?
C17 O2 1.321(4) . ?
C17 C18 1.487(6) . ?
C18 C19 1.430(5) . ?
C19 C20 1.509(6) . ?
C20 O5 1.193(5) . ?
C20 O4 1.313(5) . ?
N1 N2 1.368(4) . ?
O3A O3B 0.643(8) . ?

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
N2 C1 C14 105.8(3) . . ?
N2 C1 C2 134.8(4) . . ?
C14 C1 C2 119.4(4) . . ?
C3 C2 C1 116.4(4) . . ?
C2 C3 C4 124.0(4) . . ?
C3 C4 C5 120.2(4) . . ?
C4 C5 C14 115.4(4) . . ?
C4 C5 C6 128.4(4) . . ?
C14 C5 C6 116.2(4) . . ?
O1 C6 C5 122.5(4) . . ?
O1 C6 C7 120.8(4) . . ?
C5 C6 C7 116.7(3) . . ?
C8 C7 C12 118.1(4) . . ?
C8 C7 C6 118.1(4) . . ?
C12 C7 C6 123.8(4) . . ?
C7 C8 C9 121.2(4) . . ?
C10 C9 C8 120.3(4) . . ?
C9 C10 C11 120.3(4) . . ?
C10 C11 C12 119.8(4) . . ?
C11 C12 C7 120.3(3) . . ?
C11 C12 C13 123.0(3) . . ?
C7 C12 C13 116.7(3) . . ?
N1 C13 C14 109.2(3) . . ?
N1 C13 C12 131.9(3) . . ?
C14 C13 C12 118.8(3) . . ?
C1 C14 C5 124.7(4) . . ?
C1 C14 C13 107.4(3) . . ?
C5 C14 C13 127.9(4) . . ?
N2 C15 C16 113.0(3) . . ?
O2 C16 C15 107.2(3) . . ?
O3A C17 O3B 29.9(4) . . ?
O3A C17 O2 122.0(5) . . ?
O3B C17 O2 121.6(4) . . ?
O3A C17 C18 122.9(5) . . ?
O3B C17 C18 123.9(5) . . ?
O2 C17 C18 112.2(4) . . ?
C19 C18 C17 113.6(4) . . ?
C18 C19 C20 116.2(4) . . ?
O5 C20 O4 123.5(4) . . ?
O5 C20 C19 125.4(4) . . ?
O4 C20 C19 111.0(4) . . ?
C13 N1 N2 106.8(3) . . ?
C1 N2 N1 110.8(3) . . ?
C1 N2 C15 129.3(3) . . ?
N1 N2 C15 119.8(3) . . ?
C17 O2 C16 116.7(3) . . ?
O3B O3A C17 85.6(14) . . ?
O3A O3B C17 64.5(12) . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.053



