# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2070981'
loop_
_audit_author_name
_audit_author_address
'Uday Pratap Singh'
;Indian Institute of Technology Roorkee
India
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        HMN
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   11.2643(8)
_cell_length_b                   12.9129(9)
_cell_length_c                   9.9050(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.136(2)
_cell_angle_gamma                90
_cell_volume                     1439.73(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3904
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      24.21

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18066
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.206
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3404
_reflns_number_gt                2579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_max     0.920
_reflns_Friedel_fraction_full    0.981

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_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)+(0.0394P)²+1.0664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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 996 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3404
_refine_ls_number_parameters     220
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.4857(3) 0.9471(2) 0.7298(3) 0.0602(9) Uani 1 1 d . . . . .
H1O H 0.497(5) 0.907(5) 0.652(6) 0.10(2) Uiso 1 1 d . . . . .
O2 O 0.5892(3) 0.5685(2) 0.3211(3) 0.0562(8) Uani 1 1 d . . . . .
H2O H 0.566(6) 0.601(6) 0.395(7) 0.13(3) Uiso 1 1 d . . . . .
O3 O 0.7034(3) 0.6233(2) -0.1305(3) 0.0599(8) Uani 1 1 d . . . . .
H3O H 0.675(8) 0.551(6) -0.141(9) 0.18(3) Uiso 1 1 d . . . . .
N1 N 0.5077(3) 0.7874(3) 0.5769(3) 0.0464(8) Uani 1 1 d . . . . .
N2 N 0.5410(3) 0.7309(3) 0.4633(3) 0.0465(8) Uani 1 1 d . . . . .
C1 C 0.4413(4) 0.8807(3) 0.8211(4) 0.0430(9) Uani 1 1 d . . . . .
C2 C 0.4050(4) 0.9255(3) 0.9426(4) 0.0493(10) Uani 1 1 d . . . . .
H2A H 0.410048 0.996843 0.954707 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3628(4) 0.8651(3) 1.0418(4) 0.0481(10) Uani 1 1 d . . . . .
H3A H 0.340172 0.895532 1.122014 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3525(3) 0.7565(3) 1.0257(4) 0.0414(9) Uani 1 1 d . . . . .
C5 C 0.3076(4) 0.6948(4) 1.1290(4) 0.0517(11) Uani 1 1 d . . . . .
H5A H 0.285273 0.725669 1.208962 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2963(4) 0.5902(4) 1.1136(4) 0.0595(11) Uani 1 1 d . . . . .
H6A H 0.264870 0.550479 1.181974 0.071 Uiso 1 1 calc R U . . .
C7 C 0.3319(4) 0.5433(3) 0.9954(5) 0.0581(11) Uani 1 1 d . . . . .
H7A H 0.325402 0.471845 0.985619 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3765(4) 0.6015(3) 0.8929(4) 0.0497(10) Uani 1 1 d . . . . .
H8A H 0.399439 0.568724 0.814479 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3885(3) 0.7102(3) 0.9041(4) 0.0369(8) Uani 1 1 d . . . . .
C10 C 0.4340(3) 0.7743(3) 0.7993(3) 0.0376(8) Uani 1 1 d . . . . .
C11 C 0.4710(4) 0.7308(3) 0.6743(4) 0.0418(9) Uani 1 1 d . . . . .
H11A H 0.468342 0.659298 0.663115 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5767(4) 0.7875(3) 0.3663(4) 0.0421(9) Uani 1 1 d . . . . .
H12A H 0.578077 0.859114 0.376483 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6146(3) 0.7424(3) 0.2420(3) 0.0378(9) Uani 1 1 d . . . . .
C14 C 0.6188(4) 0.6352(3) 0.2208(4) 0.0413(9) Uani 1 1 d . . . . .
C15 C 0.6492(4) 0.5943(3) 0.0992(4) 0.0438(9) Uani 1 1 d . . . . .
H15A H 0.650203 0.522924 0.086824 0.053 Uiso 1 1 calc R U . . .
C16 C 0.6782(4) 0.6595(3) -0.0048(4) 0.0433(9) Uani 1 1 d . . . . .
C17 C 0.6801(4) 0.7665(3) 0.0135(4) 0.0437(9) Uani 1 1 d . . . . .
H17A H 0.702848 0.810244 -0.055481 0.052 Uiso 1 1 calc R U . . .
C18 C 0.6477(4) 0.8061(3) 0.1358(4) 0.0417(9) Uani 1 1 d . . . . .
H18A H 0.647888 0.877550 0.148038 0.050 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 1.355(5) . ?
O1 H1O 0.93(6) . ?
O2 C14 1.365(5) . ?
O2 H2O 0.89(7) . ?
O3 C16 1.369(4) . ?
O3 H3O 0.99(8) . ?
N1 C11 1.291(5) . ?
N1 N2 1.403(4) . ?
N2 C12 1.283(5) . ?
C1 C10 1.393(5) . ?
C1 C2 1.410(5) . ?
C2 C3 1.355(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.416(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.406(5) . ?
C4 C9 1.417(5) . ?
C5 C6 1.364(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.391(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.373(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.414(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.436(5) . ?
C10 C11 1.436(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.442(5) . ?
C12 H12A 0.9300 . ?
C13 C18 1.398(5) . ?
C13 C14 1.401(5) . ?
C14 C15 1.370(6) . ?
C15 C16 1.379(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.394(5) . ?
C17 C18 1.376(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
C1 O1 H1O 105(4) . . ?
C14 O2 H2O 113(5) . . ?
C16 O3 H3O 110(6) . . ?
C11 N1 N2 114.1(3) . . ?
C12 N2 N1 113.9(3) . . ?
O1 C1 C10 122.9(3) . . ?
O1 C1 C2 115.8(3) . . ?
C10 C1 C2 121.3(4) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 121.2(4) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 C9 120.1(4) . . ?
C3 C4 C9 119.3(3) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C7 C8 C9 121.5(4) . . ?
C7 C8 H8A 119.3 . . ?
C9 C8 H8A 119.3 . . ?
C8 C9 C4 117.1(3) . . ?
C8 C9 C10 123.4(4) . . ?
C4 C9 C10 119.5(3) . . ?
C1 C10 C11 120.1(4) . . ?
C1 C10 C9 118.5(3) . . ?
C11 C10 C9 121.4(3) . . ?
N1 C11 C10 122.3(3) . . ?
N1 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
N2 C12 C13 121.3(4) . . ?
N2 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C18 C13 C14 117.2(3) . . ?
C18 C13 C12 120.1(3) . . ?
C14 C13 C12 122.7(3) . . ?
O2 C14 C15 118.2(3) . . ?
O2 C14 C13 120.3(3) . . ?
C15 C14 C13 121.5(3) . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
O3 C16 C15 122.3(3) . . ?
O3 C16 C17 117.0(3) . . ?
C15 C16 C17 120.7(3) . . ?
C18 C17 C16 118.7(3) . . ?
C18 C17 H17A 120.7 . . ?
C16 C17 H17A 120.7 . . ?
C17 C18 C13 122.0(3) . . ?
C17 C18 H18A 119.0 . . ?
C13 C18 H18A 119.0 . . ?

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
C11 N1 N2 C12 179.5(4) . . . . ?
O1 C1 C2 C3 -178.0(4) . . . . ?
C10 C1 C2 C3 0.5(7) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
C2 C3 C4 C9 0.8(6) . . . . ?
C3 C4 C5 C6 179.3(4) . . . . ?
C9 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C7 1.4(7) . . . . ?
C5 C6 C7 C8 -1.1(7) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C7 C8 C9 C4 0.1(6) . . . . ?
C7 C8 C9 C10 -179.6(4) . . . . ?
C5 C4 C9 C8 0.1(6) . . . . ?
C3 C4 C9 C8 180.0(4) . . . . ?
C5 C4 C9 C10 179.9(3) . . . . ?
C3 C4 C9 C10 -0.3(5) . . . . ?
O1 C1 C10 C11 -1.9(6) . . . . ?
C2 C1 C10 C11 179.7(4) . . . . ?
O1 C1 C10 C9 178.3(3) . . . . ?
C2 C1 C10 C9 -0.1(6) . . . . ?
C8 C9 C10 C1 179.7(4) . . . . ?
C4 C9 C10 C1 0.0(5) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C4 C9 C10 C11 -179.8(4) . . . . ?
N2 N1 C11 C10 179.5(3) . . . . ?
C1 C10 C11 N1 -2.5(6) . . . . ?
C9 C10 C11 N1 177.2(3) . . . . ?
N1 N2 C12 C13 179.8(3) . . . . ?
N2 C12 C13 C18 177.0(4) . . . . ?
N2 C12 C13 C14 -2.2(6) . . . . ?
C18 C13 C14 O2 179.1(4) . . . . ?
C12 C13 C14 O2 -1.7(6) . . . . ?
C18 C13 C14 C15 -2.7(6) . . . . ?
C12 C13 C14 C15 176.5(4) . . . . ?
O2 C14 C15 C16 179.3(4) . . . . ?
C13 C14 C15 C16 1.0(7) . . . . ?
C14 C15 C16 O3 -176.6(4) . . . . ?
C14 C15 C16 C17 1.7(7) . . . . ?
O3 C16 C17 C18 175.8(4) . . . . ?
C15 C16 C17 C18 -2.6(6) . . . . ?
C16 C17 C18 C13 0.8(6) . . . . ?
C14 C13 C18 C17 1.8(6) . . . . ?
C12 C13 C18 C17 -177.5(4) . . . . ?

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
O1 H1O N1 0.93(6) 1.73(6) 2.576(5) 150(5) . yes
O2 H2O N2 0.89(7) 1.83(7) 2.596(5) 142(6) . yes
O3 H3O O2 0.99(8) 1.86(9) 2.824(4) 166(8) 2_564 yes

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_preparation       Luminescent
