# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_liu162m
_audit_block_doi                 10.5517/ccdc.csd.cc1z4hcz
_database_code_depnum_ccdc_archive 'CCDC 1821571'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly' 'National Institute of Technology Trichy'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         349.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2895(4)
_cell_length_b                   6.6468(2)
_cell_length_c                   14.8855(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.0494(10)
_cell_angle_gamma                90
_cell_volume                     1570.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.8093
_cell_measurement_theta_max      33.1264
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            29957
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         33.24
_diffrn_reflns_theta_full        33.24
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             5986
_reflns_number_gt                4798
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1268
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_number_reflns         5986
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.4417P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.15362(6) 0.09715(15) 0.92288(7) 0.01484(18) Uani d . . . 1 . .
C C2 0.11345(7) 0.06997(17) 0.99521(8) 0.0199(2) Uani d . . . 1 . .
H H2 0.100552 -0.061608 1.012815 0.024 Uiso calc U . R 1 . .
C C3 0.09246(7) 0.23652(18) 1.04127(8) 0.0222(2) Uani d . . . 1 . .
H H3 0.064671 0.218801 1.090377 0.027 Uiso calc U . R 1 . .
C C4 0.11177(7) 0.43012(17) 1.01618(8) 0.0213(2) Uani d . . . 1 . .
H H4 0.096649 0.543639 1.047718 0.026 Uiso calc U . R 1 . .
C C5 0.15291(6) 0.45640(16) 0.94539(8) 0.01822(19) Uani d . . . 1 . .
H H5 0.167111 0.588104 0.929265 0.022 Uiso calc U . R 1 . .
C C6 0.17381(6) 0.29022(15) 0.89727(7) 0.01474(17) Uani d . . . 1 . .
C C7 0.21806(6) 0.31432(14) 0.82166(7) 0.01506(18) Uani d . . . 1 . .
C C8 0.22459(6) 0.13624(14) 0.76894(7) 0.01404(17) Uani d . . . 1 . .
C C9 0.17943(6) -0.05115(14) 0.78633(7) 0.01519(18) Uani d . . . 1 . .
H H9 0.20919 -0.170548 0.767921 0.018 Uiso calc U . R 1 . .
C C10 0.05173(7) -0.22764(19) 0.73047(9) 0.0274(3) Uani d . . . 1 . .
H H10A 0.085992 -0.339706 0.716655 0.041 Uiso calc U . R 1 . .
H H10B -0.001065 -0.221056 0.683394 0.041 Uiso calc U . R 1 . .
H H10C 0.03918 -0.248444 0.791154 0.041 Uiso calc U . R 1 . .
C C11 0.26499(6) 0.13534(14) 0.69817(7) 0.01492(18) Uani d . . . 1 . .
H H11 0.268639 0.011539 0.667413 0.018 Uiso calc U . R 1 . .
C C12 0.34010(6) 0.30546(14) 0.59580(7) 0.01360(17) Uani d . . . 1 . .
C C13 0.37230(6) 0.14106(14) 0.56269(7) 0.01562(18) Uani d . . . 1 . .
H H13 0.368462 0.015502 0.591953 0.019 Uiso calc U . R 1 . .
C C14 0.41229(6) 0.32272(14) 0.44472(7) 0.01470(18) Uani d . . . 1 . .
C C15 0.44836(6) 0.31533(16) 0.36843(8) 0.01853(19) Uani d . . . 1 . .
H H15 0.471396 0.193464 0.351564 0.022 Uiso calc U . R 1 . .
C C16 0.44997(7) 0.48838(18) 0.31790(8) 0.0202(2) Uani d . . . 1 . .
H H16 0.474947 0.486115 0.26608 0.024 Uiso calc U . R 1 . .
C C17 0.41519(7) 0.66757(17) 0.34208(8) 0.0202(2) Uani d . . . 1 . .
H H17 0.414764 0.784482 0.305266 0.024 Uiso calc U . R 1 . .
C C18 0.38167(6) 0.67493(15) 0.41892(7) 0.01713(19) Uani d . . . 1 . .
H H18 0.358995 0.797502 0.435524 0.021 Uiso calc U . R 1 . .
C C19 0.38079(6) 0.50162(14) 0.47310(7) 0.01396(17) Uani d . . . 1 . .
C C20 0.34745(6) 0.50447(14) 0.55650(7) 0.01374(17) Uani d . . . 1 . .
N N1 0.30007(5) 0.29943(13) 0.66919(6) 0.01490(16) Uani d . . . 1 . .
H H1N 0.2921(9) 0.415(2) 0.6964(10) 0.022 Uiso d U . . 1 . .
O O1 0.17547(5) -0.07212(11) 0.88120(5) 0.01653(15) Uani d . . . 1 . .
O O2 0.24841(5) 0.48030(11) 0.80618(6) 0.02026(16) Uani d . . . 1 . .
O O3 0.40966(5) 0.14524(11) 0.49025(5) 0.01710(15) Uani d . . . 1 . .
O O4 0.32690(5) 0.65857(11) 0.59217(6) 0.01920(16) Uani d . . . 1 . .
O O5 0.09714(4) -0.04315(11) 0.73075(6) 0.01815(16) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.3701(12) ?
C1 C2 . 1.3923(15) ?
C1 C6 . 1.3989(13) ?
C2 C3 . 1.3850(16) ?
C3 C4 . 1.3955(16) ?
C4 C5 . 1.3818(16) ?
C5 C6 . 1.3996(14) ?
C6 C7 . 1.4760(15) ?
C7 O2 . 1.2514(12) ?
C7 C8 . 1.4374(14) ?
C8 C11 . 1.3624(14) ?
C8 C9 . 1.4985(13) ?
C9 O5 . 1.4083(12) ?
C9 O1 . 1.4349(13) ?
C10 O5 . 1.4316(13) ?
C11 N1 . 1.3466(12) ?
C12 C13 . 1.3523(13) ?
C12 N1 . 1.3936(13) ?
C12 C20 . 1.4622(13) ?
C13 O3 . 1.3528(13) ?
C14 O3 . 1.3660(12) ?
C14 C15 . 1.3923(15) ?
C14 C19 . 1.3977(13) ?
C15 C16 . 1.3778(16) ?
C16 C17 . 1.4004(16) ?
C17 C18 . 1.3750(15) ?
C18 C19 . 1.4081(14) ?
C19 C20 . 1.4633(14) ?
C20 O4 . 1.2343(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 117.33(9) ?
O1 C1 C6 . . 121.93(9) ?
C2 C1 C6 . . 120.68(9) ?
C3 C2 C1 . . 119.39(10) ?
C2 C3 C4 . . 120.59(10) ?
C5 C4 C3 . . 119.87(10) ?
C4 C5 C6 . . 120.43(10) ?
C1 C6 C5 . . 119.03(9) ?
C1 C6 C7 . . 119.52(9) ?
C5 C6 C7 . . 121.44(9) ?
O2 C7 C8 . . 122.99(10) ?
O2 C7 C6 . . 121.15(9) ?
C8 C7 C6 . . 115.85(8) ?
C11 C8 C7 . . 122.27(9) ?
C11 C8 C9 . . 118.14(9) ?
C7 C8 C9 . . 119.37(9) ?
O5 C9 O1 . . 109.48(8) ?
O5 C9 C8 . . 107.84(8) ?
O1 C9 C8 . . 112.56(8) ?
N1 C11 C8 . . 123.92(9) ?
C13 C12 N1 . . 123.45(9) ?
C13 C12 C20 . . 120.77(9) ?
N1 C12 C20 . . 115.77(8) ?
C12 C13 O3 . . 123.73(9) ?
O3 C14 C15 . . 116.14(9) ?
O3 C14 C19 . . 122.00(9) ?
C15 C14 C19 . . 121.86(9) ?
C16 C15 C14 . . 118.64(10) ?
C15 C16 C17 . . 120.73(10) ?
C18 C17 C16 . . 120.25(10) ?
C17 C18 C19 . . 120.30(10) ?
C14 C19 C18 . . 118.10(9) ?
C14 C19 C20 . . 119.96(9) ?
C18 C19 C20 . . 121.94(9) ?
O4 C20 C12 . . 121.60(9) ?
O4 C20 C19 . . 124.36(9) ?
C12 C20 C19 . . 114.04(8) ?
C11 N1 C12 . . 125.58(9) ?
C1 O1 C9 . . 116.09(7) ?
C13 O3 C14 . . 118.91(8) ?
C9 O5 C10 . . 113.08(8) ?

