# Electronic Supplementary Material (ESI) for ChemComm.
# 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_KA837_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1975072'
loop_
_audit_author_name
_audit_author_address
'B Sridhar'
;Principal Scientist
India
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-02-18 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         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.053(5)
_cell_length_b                   18.102(12)
_cell_length_c                   11.924(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.894(10)
_cell_angle_gamma                90
_cell_volume                     1456.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9682
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      27.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6221
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13457
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         30.641
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4364
_reflns_number_gt                2605
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1303P)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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.094(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.2169
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.4831(2) 0.57465(9) 0.25683(14) 0.0368(4) Uani 1 1 d . . . . .
H1 H 0.460496 0.547081 0.322509 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6755(2) 0.54567(10) 0.23592(15) 0.0419(4) Uani 1 1 d . . . . .
C3 C 0.6486(3) 0.46973(10) 0.18196(16) 0.0484(5) Uani 1 1 d . . . . .
H3 H 0.761922 0.442937 0.183696 0.058 Uiso 1 1 calc R U . . .
C4 C 0.4739(3) 0.43834(10) 0.13199(16) 0.0481(4) Uani 1 1 d . . . . .
H4 H 0.469389 0.390720 0.102041 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2871(3) 0.47784(9) 0.12332(14) 0.0436(4) Uani 1 1 d . . . . .
C6 C 0.3072(2) 0.56014(9) 0.14764(14) 0.0381(4) Uani 1 1 d . . . . .
H6 H 0.334226 0.584466 0.080472 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5009(2) 0.65616(9) 0.28928(14) 0.0383(4) Uani 1 1 d . . . . .
C8 C 0.6230(2) 0.69738(10) 0.24668(16) 0.0441(4) Uani 1 1 d . . . . .
C9 C 0.7479(3) 0.66692(10) 0.17374(19) 0.0532(5) Uani 1 1 d . . . . .
H9A H 0.720264 0.695046 0.101537 0.064 Uiso 1 1 calc R U . . .
H9B H 0.886505 0.674236 0.216019 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3866(2) 0.68497(9) 0.36749(14) 0.0397(4) Uani 1 1 d . . . . .
C11 C 0.3723(3) 0.64362(11) 0.46381(16) 0.0551(5) Uani 1 1 d . . . . .
H11 H 0.435450 0.598063 0.479227 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2651(4) 0.66953(12) 0.53682(18) 0.0681(6) Uani 1 1 d . . . . .
H12 H 0.256231 0.640865 0.599810 0.082 Uiso 1 1 calc R U . . .
C13 C 0.1718(3) 0.73735(12) 0.51689(18) 0.0614(6) Uani 1 1 d . . . . .
H13 H 0.101588 0.754700 0.566548 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1840(3) 0.77903(12) 0.42243(17) 0.0523(5) Uani 1 1 d . . . . .
H14 H 0.121836 0.824833 0.408431 0.063 Uiso 1 1 calc R U . . .
C15 C 0.2887(3) 0.75299(10) 0.34780(15) 0.0443(4) Uani 1 1 d . . . . .
H15 H 0.293629 0.781400 0.283713 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8479(3) 0.54548(13) 0.34813(19) 0.0620(6) Uani 1 1 d . . . . .
H16A H 0.965879 0.529045 0.330993 0.093 Uiso 1 1 calc R U . . .
H16B H 0.818378 0.512740 0.404147 0.093 Uiso 1 1 calc R U . . .
H16C H 0.867980 0.594551 0.379934 0.093 Uiso 1 1 calc R U . . .
N1 N 0.6552(3) 0.77329(9) 0.27794(16) 0.0582(5) Uani 1 1 d . . . . .
N2 N 0.7461(3) 0.81082(9) 0.22320(17) 0.0611(5) Uani 1 1 d . . . . .
N3 N 0.8250(4) 0.85197(12) 0.1808(2) 0.0834(7) Uani 1 1 d . . . . .
O1 O 0.1268(2) 0.44719(8) 0.09726(14) 0.0644(4) Uani 1 1 d . . . . .
O2 O 0.13443(18) 0.59101(8) 0.16362(14) 0.0559(4) Uani 1 1 d . . . . .
H2O H 0.044(5) 0.5678(16) 0.111(3) 0.108(11) Uiso 1 1 d . . . . .
O3 O 0.71704(16) 0.59139(7) 0.14539(11) 0.0451(3) Uani 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
C1 C7 1.521(2) . ?
C1 C6 1.538(2) . ?
C1 C2 1.542(2) . ?
C1 H1 0.9800 . ?
C2 O3 1.456(2) . ?
C2 C3 1.506(3) . ?
C2 C16 1.524(3) . ?
C3 C4 1.330(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.476(3) . ?
C4 H4 0.9300 . ?
C5 O1 1.216(2) . ?
C5 C6 1.516(3) . ?
C6 O2 1.403(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.346(2) . ?
C7 C10 1.493(2) . ?
C8 N1 1.425(2) . ?
C8 C9 1.511(2) . ?
C9 O3 1.410(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.398(3) . ?
C10 C11 1.399(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.242(2) . ?
N2 N3 1.133(3) . ?
O2 H2O 0.86(3) . ?

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
C7 C1 C6 111.58(13) . . ?
C7 C1 C2 111.09(13) . . ?
C6 C1 C2 109.66(13) . . ?
C7 C1 H1 108.1 . . ?
C6 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
O3 C2 C3 103.28(14) . . ?
O3 C2 C16 111.80(15) . . ?
C3 C2 C16 110.03(15) . . ?
O3 C2 C1 107.61(13) . . ?
C3 C2 C1 111.84(14) . . ?
C16 C2 C1 111.96(15) . . ?
C4 C3 C2 124.53(16) . . ?
C4 C3 H3 117.7 . . ?
C2 C3 H3 117.7 . . ?
C3 C4 C5 121.07(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
O1 C5 C4 122.79(17) . . ?
O1 C5 C6 121.69(16) . . ?
C4 C5 C6 115.51(14) . . ?
O2 C6 C5 112.37(14) . . ?
O2 C6 C1 109.62(14) . . ?
C5 C6 C1 109.72(13) . . ?
O2 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
C1 C6 H6 108.3 . . ?
C8 C7 C10 124.28(16) . . ?
C8 C7 C1 117.14(14) . . ?
C10 C7 C1 118.57(13) . . ?
C7 C8 N1 120.46(15) . . ?
C7 C8 C9 124.01(16) . . ?
N1 C8 C9 115.30(14) . . ?
O3 C9 C8 114.63(14) . . ?
O3 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
O3 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C15 C10 C11 117.33(16) . . ?
C15 C10 C7 122.19(15) . . ?
C11 C10 C7 120.47(17) . . ?
C12 C11 C10 121.07(19) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 120.74(19) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 119.17(18) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.46(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 121.22(17) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 N1 C8 117.24(16) . . ?
N3 N2 N1 171.8(2) . . ?
C6 O2 H2O 102(2) . . ?
C9 O3 C2 115.07(13) . . ?

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
C7 C1 C2 O3 -56.48(17) . . . . ?
C6 C1 C2 O3 67.33(17) . . . . ?
C7 C1 C2 C3 -169.23(14) . . . . ?
C6 C1 C2 C3 -45.43(18) . . . . ?
C7 C1 C2 C16 66.75(19) . . . . ?
C6 C1 C2 C16 -169.44(16) . . . . ?
O3 C2 C3 C4 -100.1(2) . . . . ?
C16 C2 C3 C4 140.5(2) . . . . ?
C1 C2 C3 C4 15.4(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 O1 -166.91(18) . . . . ?
C3 C4 C5 C6 13.8(3) . . . . ?
O1 C5 C6 O2 14.0(2) . . . . ?
C4 C5 C6 O2 -166.73(15) . . . . ?
O1 C5 C6 C1 136.23(17) . . . . ?
C4 C5 C6 C1 -44.51(19) . . . . ?
C7 C1 C6 O2 -52.47(17) . . . . ?
C2 C1 C6 O2 -175.99(14) . . . . ?
C7 C1 C6 C5 -176.32(12) . . . . ?
C2 C1 C6 C5 60.16(17) . . . . ?
C6 C1 C7 C8 -93.78(18) . . . . ?
C2 C1 C7 C8 28.9(2) . . . . ?
C6 C1 C7 C10 87.46(18) . . . . ?
C2 C1 C7 C10 -149.84(14) . . . . ?
C10 C7 C8 N1 1.8(3) . . . . ?
C1 C7 C8 N1 -176.83(15) . . . . ?
C10 C7 C8 C9 176.04(16) . . . . ?
C1 C7 C8 C9 -2.6(3) . . . . ?
C7 C8 C9 O3 4.4(3) . . . . ?
N1 C8 C9 O3 178.85(17) . . . . ?
C8 C7 C10 C15 42.8(2) . . . . ?
C1 C7 C10 C15 -138.51(17) . . . . ?
C8 C7 C10 C11 -137.8(2) . . . . ?
C1 C7 C10 C11 40.8(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C7 C10 C11 C12 -179.51(19) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C11 C10 C15 C14 1.1(3) . . . . ?
C7 C10 C15 C14 -179.58(16) . . . . ?
C7 C8 N1 N2 -169.96(18) . . . . ?
C9 C8 N1 N2 15.4(3) . . . . ?
C8 C9 O3 C2 -35.2(2) . . . . ?
C3 C2 O3 C9 179.67(14) . . . . ?
C16 C2 O3 C9 -62.07(18) . . . . ?
C1 C2 O3 C9 61.26(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2O O1 0.86(3) 2.28(3) 2.717(3) 112(3) . yes
O2 H2O O1 0.86(3) 2.44(4) 3.197(3) 146(3) 3_565 yes

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.125

