# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_f
_audit_block_doi                 10.5517/ccdc.csd.cc24ty1z
_database_code_depnum_ccdc_archive 'CCDC 1991131'
loop_
_audit_author_name
_audit_author_address
'Paula Brandao'
;Indian institute of engineering science and technology, SHIBPUR
India
;
_audit_update_record             
;
2020-03-18 deposited with the CCDC.	2020-11-11 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         ?
_chemical_formula_sum            'C26 H21 N3 O5'
_chemical_formula_weight         455.46

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.8611(3)
_cell_length_b                   15.2401(11)
_cell_length_c                   28.170(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2086.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    602
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4368
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29297
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.673
_diffrn_reflns_theta_max         25.773
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3962
_reflns_number_gt                3627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0785P)²+10.8627P] 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 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3962
_refine_ls_number_parameters     312
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0984
_refine_ls_wR_factor_ref         0.2748
_refine_ls_wR_factor_gt          0.2716
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_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 0.4114(14) 0.6316(4) 0.3364(2) 0.0373(16) Uani 1 1 d . . . . .
O2 O 0.4567(15) 0.4580(5) 0.2062(2) 0.0417(17) Uani 1 1 d . . . . .
O3 O 0.6096(11) 0.4401(5) 0.3402(2) 0.0337(15) Uani 1 1 d . . . . .
O4 O -0.1154(13) 0.3289(5) 0.4355(2) 0.0377(16) Uani 1 1 d . . . . .
O5 O 0.1510(13) 0.3714(4) 0.4961(2) 0.0339(15) Uani 1 1 d . . . . .
N1 N 0.4247(15) 0.5471(5) 0.2697(3) 0.0289(17) Uani 1 1 d . . . . .
N2 N 0.1862(14) 0.4296(5) 0.3731(2) 0.0278(16) Uani 1 1 d . . . . .
H2 H 0.007585 0.426724 0.368304 0.033 Uiso 1 1 calc R U . . .
N3 N -0.1569(16) 0.6569(5) 0.4603(3) 0.0340(19) Uani 1 1 d . . . . .
H3A H -0.289788 0.691517 0.450319 0.041 Uiso 1 1 calc R U . . .
C1 C 0.5039(19) 0.6207(5) 0.2974(3) 0.0258(18) Uani 1 1 d . . . . .
C2 C 0.7270(19) 0.6757(6) 0.2761(3) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.825(2) 0.7468(6) 0.3022(4) 0.035(2) Uani 1 1 d . . . . .
H3 H 0.753352 0.758501 0.332878 0.042 Uiso 1 1 calc R U . . .
C4 C 1.034(2) 0.8021(6) 0.2828(4) 0.037(2) Uani 1 1 d . . . . .
H4 H 1.110295 0.848233 0.301237 0.044 Uiso 1 1 calc R U . . .
C5 C 1.121(2) 0.7877(6) 0.2375(4) 0.037(2) Uani 1 1 d . . . . .
H5 H 1.251566 0.826762 0.224019 0.044 Uiso 1 1 calc R U . . .
C6 C 1.0246(19) 0.7169(7) 0.2100(3) 0.034(2) Uani 1 1 d . . . . .
C7 C 0.8199(18) 0.6596(6) 0.2303(3) 0.0286(19) Uani 1 1 d . . . . .
C8 C 1.109(2) 0.7005(7) 0.1634(4) 0.044(3) Uani 1 1 d . . . . .
H8 H 1.234047 0.739990 0.148676 0.053 Uiso 1 1 calc R U . . .
C9 C 1.017(2) 0.6286(8) 0.1380(4) 0.049(3) Uani 1 1 d . . . . .
H9 H 1.084067 0.617817 0.106804 0.059 Uiso 1 1 calc R U . . .
C10 C 0.821(2) 0.5709(8) 0.1590(4) 0.044(3) Uani 1 1 d . . . . .
H10 H 0.755460 0.521595 0.141841 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7295(19) 0.5867(6) 0.2037(3) 0.030(2) Uani 1 1 d . . . . .
C12 C 0.5250(19) 0.5254(6) 0.2255(3) 0.030(2) Uani 1 1 d . . . . .
C13 C 0.2284(18) 0.4884(7) 0.2933(3) 0.035(2) Uani 1 1 d . . . . .
H13A H 0.174734 0.440702 0.271267 0.042 Uiso 1 1 calc R U . . .
H13B H 0.060527 0.521556 0.301885 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3552(18) 0.4497(6) 0.3373(3) 0.0278(18) Uani 1 1 d . . . . .
C15 C 0.2967(17) 0.4126(6) 0.4196(3) 0.0260(19) Uani 1 1 d D . . . .
H15 H 0.421(19) 0.370(6) 0.413(4) 0.05(3) Uiso 1 1 d D . . . .
C16 C 0.4077(17) 0.4975(6) 0.4418(3) 0.0266(18) Uani 1 1 d . . . . .
H16A H 0.526271 0.482057 0.469162 0.032 Uiso 1 1 calc R U . . .
H16B H 0.524286 0.527856 0.418141 0.032 Uiso 1 1 calc R U . . .
C17 C 0.1878(16) 0.5603(5) 0.4586(3) 0.0243(18) Uani 1 1 d . . . . .
C18 C 0.1353(17) 0.5807(6) 0.5069(3) 0.0293(19) Uani 1 1 d . . . . .
C19 C 0.248(2) 0.5577(6) 0.5502(3) 0.033(2) Uani 1 1 d . . . . .
H19 H 0.391941 0.515741 0.551522 0.040 Uiso 1 1 calc R U . . .
C20 C 0.151(2) 0.5957(8) 0.5921(4) 0.045(3) Uani 1 1 d . . . . .
H20 H 0.230090 0.580005 0.621727 0.054 Uiso 1 1 calc R U . . .
C21 C -0.066(2) 0.6579(8) 0.5903(4) 0.046(3) Uani 1 1 d . . . . .
H21 H -0.130205 0.684283 0.618808 0.055 Uiso 1 1 calc R U . . .
C22 C -0.183(2) 0.6800(7) 0.5483(4) 0.040(2) Uani 1 1 d . . . . .
H22 H -0.332511 0.720141 0.547914 0.048 Uiso 1 1 calc R U . . .
C23 C -0.0892(19) 0.6454(6) 0.5064(4) 0.033(2) Uani 1 1 d . . . . .
C24 C 0.0091(17) 0.6076(6) 0.4311(3) 0.0285(19) Uani 1 1 d . . . . .
H24 H 0.000918 0.606535 0.397403 0.034 Uiso 1 1 calc R U . . .
C25 C 0.0878(16) 0.3672(5) 0.4505(3) 0.0245(18) Uani 1 1 d . . . . .
C26 C -0.047(2) 0.3375(7) 0.5297(4) 0.039(2) Uani 1 1 d . . . . .
H26A H -0.233033 0.354465 0.519695 0.059 Uiso 1 1 calc R U . . .
H26B H -0.009462 0.361715 0.561211 0.059 Uiso 1 1 calc R U . . .
H26C H -0.033977 0.273379 0.530788 0.059 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
O1 C1 1.199(11) . ?
O2 C12 1.210(11) . ?
O3 C14 1.248(11) . ?
O4 C25 1.222(11) . ?
O5 C25 1.324(11) . ?
O5 C26 1.445(11) . ?
N1 C12 1.376(11) . ?
N1 C1 1.420(11) . ?
N1 C13 1.467(11) . ?
N2 C14 1.338(11) . ?
N2 C15 1.439(11) . ?
N2 H2 0.8800 . ?
N3 C23 1.349(13) . ?
N3 C24 1.377(12) . ?
N3 H3A 0.8800 . ?
C1 C2 1.497(12) . ?
C2 C7 1.388(13) . ?
C2 C3 1.393(13) . ?
C3 C4 1.425(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(14) . ?
C5 H5 0.9500 . ?
C6 C8 1.398(14) . ?
C6 C7 1.444(13) . ?
C7 C11 1.410(13) . ?
C8 C9 1.382(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.426(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.358(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.496(12) . ?
C13 C14 1.505(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C25 1.504(11) . ?
C15 C16 1.536(11) . ?
C15 H15 0.91(3) . ?
C16 C17 1.510(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C24 1.369(12) . ?
C17 C18 1.419(13) . ?
C18 C19 1.382(13) . ?
C18 C23 1.471(13) . ?
C19 C20 1.396(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.419(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.354(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(14) . ?
C22 H22 0.9500 . ?
C24 H24 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C25 O5 C26 117.6(7) . . ?
C12 N1 C1 126.2(7) . . ?
C12 N1 C13 119.5(7) . . ?
C1 N1 C13 114.1(7) . . ?
C14 N2 C15 120.0(7) . . ?
C14 N2 H2 120.0 . . ?
C15 N2 H2 120.0 . . ?
C23 N3 C24 111.1(8) . . ?
C23 N3 H3A 124.4 . . ?
C24 N3 H3A 124.4 . . ?
O1 C1 N1 120.9(8) . . ?
O1 C1 C2 124.1(8) . . ?
N1 C1 C2 114.7(7) . . ?
C7 C2 C3 121.0(8) . . ?
C7 C2 C1 120.6(8) . . ?
C3 C2 C1 118.3(8) . . ?
C2 C3 C4 120.1(9) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 118.9(9) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.4(9) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C8 C6 C5 123.8(9) . . ?
C8 C6 C7 117.9(9) . . ?
C5 C6 C7 118.3(9) . . ?
C2 C7 C11 122.2(8) . . ?
C2 C7 C6 119.1(9) . . ?
C11 C7 C6 118.7(8) . . ?
C9 C8 C6 122.2(10) . . ?
C9 C8 H8 118.9 . . ?
C6 C8 H8 118.9 . . ?
C8 C9 C10 119.3(10) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 119.8(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C7 122.0(9) . . ?
C10 C11 C12 119.3(9) . . ?
C7 C11 C12 118.7(8) . . ?
O2 C12 N1 120.9(8) . . ?
O2 C12 C11 121.9(9) . . ?
N1 C12 C11 117.2(7) . . ?
N1 C13 C14 110.2(7) . . ?
N1 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N1 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
O3 C14 N2 122.1(8) . . ?
O3 C14 C13 120.4(8) . . ?
N2 C14 C13 117.4(7) . . ?
N2 C15 C25 110.8(7) . . ?
N2 C15 C16 110.5(7) . . ?
C25 C15 C16 113.0(7) . . ?
N2 C15 H15 101(7) . . ?
C25 C15 H15 104(7) . . ?
C16 C15 H15 117(8) . . ?
C17 C16 C15 114.4(7) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C24 C17 C18 108.3(8) . . ?
C24 C17 C16 127.3(8) . . ?
C18 C17 C16 124.4(8) . . ?
C19 C18 C17 136.1(9) . . ?
C19 C18 C23 118.1(8) . . ?
C17 C18 C23 105.7(8) . . ?
C18 C19 C20 120.5(9) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 119.9(10) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.6(10) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 121.1(10) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
N3 C23 C22 134.1(9) . . ?
N3 C23 C18 106.2(8) . . ?
C22 C23 C18 119.7(9) . . ?
C17 C24 N3 108.7(8) . . ?
C17 C24 H24 125.6 . . ?
N3 C24 H24 125.6 . . ?
O4 C25 O5 123.1(8) . . ?
O4 C25 C15 124.5(9) . . ?
O5 C25 C15 112.4(7) . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.117

