# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_KA1158_0m
_database_code_depnum_ccdc_archive 'CCDC 2242817'
loop_
_audit_author_name
_audit_author_address
'Dr. B Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-06-09 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         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32

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                   10.2278(10)
_cell_length_b                   8.9747(9)
_cell_length_c                   15.8181(18)
_cell_angle_alpha                90
_cell_angle_beta                 106.584(4)
_cell_angle_gamma                90
_cell_volume                     1391.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7980
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      30.06

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6346
_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            19970
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         30.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4259
_reflns_number_gt                2401
_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)+(0.0771P)²+0.4398P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4259
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.71871(16) 0.56710(18) 0.31402(11) 0.0340(4) Uani 1 1 d . . . . .
C2 C 0.74906(17) 0.5025(2) 0.24113(12) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.702977 0.417284 0.215246 0.049 Uiso 1 1 calc R U . . .
C3 C 0.84773(19) 0.5655(2) 0.20752(13) 0.0498(5) Uani 1 1 d . . . . .
H3 H 0.868296 0.521694 0.159572 0.060 Uiso 1 1 calc R U . . .
C4 C 0.91561(19) 0.6933(2) 0.24518(14) 0.0541(5) Uani 1 1 d . . . . .
H4 H 0.981739 0.735292 0.222596 0.065 Uiso 1 1 calc R U . . .
C5 C 0.88523(19) 0.7580(2) 0.31579(14) 0.0503(5) Uani 1 1 d . . . . .
H5 H 0.930379 0.844347 0.340609 0.060 Uiso 1 1 calc R U . . .
C6 C 0.78797(17) 0.6957(2) 0.35042(12) 0.0422(4) Uani 1 1 d . . . . .
H6 H 0.768688 0.740407 0.398550 0.051 Uiso 1 1 calc R U . . .
C7 C 0.60704(15) 0.50805(18) 0.34707(11) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.50170(17) 0.60541(19) 0.35799(12) 0.0389(4) Uani 1 1 d . . . . .
C9 C 0.39477(16) 0.51146(19) 0.37893(11) 0.0372(4) Uani 1 1 d . . . . .
C10 C 0.43709(16) 0.35246(19) 0.38106(12) 0.0392(4) Uani 1 1 d . . . . .
H10A H 0.374241 0.295536 0.334813 0.047 Uiso 1 1 calc R U . . .
H10B H 0.442660 0.307252 0.437688 0.047 Uiso 1 1 calc R U . . .
C11 C 0.57665(15) 0.36242(18) 0.36577(11) 0.0333(4) Uani 1 1 d . . . . .
C12 C 0.28224(18) 0.5687(2) 0.39233(13) 0.0467(5) Uani 1 1 d . . . . .
H12 H 0.269160 0.671218 0.387021 0.056 Uiso 1 1 calc R U . . .
C13 C 0.18082(19) 0.4804(2) 0.41443(14) 0.0501(5) Uani 1 1 d . . . . .
C14 C 0.60048(18) 0.08977(19) 0.38433(13) 0.0440(4) Uani 1 1 d . . . . .
H14A H 0.607744 0.026756 0.336055 0.053 Uiso 1 1 calc R U . . .
H14B H 0.505082 0.095488 0.382702 0.053 Uiso 1 1 calc R U . . .
C15 C 0.68209(19) 0.0235(2) 0.47079(14) 0.0466(5) Uani 1 1 d . . . . .
H15A H 0.669747 0.083388 0.518993 0.056 Uiso 1 1 calc R U . . .
H15B H 0.649058 -0.076170 0.476602 0.056 Uiso 1 1 calc R U . . .
C16 C 0.87431(18) 0.1616(2) 0.46566(13) 0.0458(4) Uani 1 1 d . . . . .
H16A H 0.969655 0.153110 0.467576 0.055 Uiso 1 1 calc R U . . .
H16B H 0.868995 0.224049 0.514626 0.055 Uiso 1 1 calc R U . . .
C17 C 0.79756(17) 0.2356(2) 0.38055(14) 0.0455(5) Uani 1 1 d . . . . .
H17A H 0.831060 0.336300 0.378744 0.055 Uiso 1 1 calc R U . . .
H17B H 0.811670 0.180798 0.331024 0.055 Uiso 1 1 calc R U . . .
O1 O 0.49339(14) 0.74264(14) 0.35119(11) 0.0605(4) Uani 1 1 d . . . . .
O2 O 0.82295(13) 0.01721(14) 0.47618(9) 0.0507(4) Uani 1 1 d . . . . .
N1 N 0.0999(2) 0.4104(2) 0.43286(14) 0.0703(6) Uani 1 1 d . . . . .
N2 N 0.65178(14) 0.23908(15) 0.37427(10) 0.0404(4) 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 C6 1.390(2) . ?
C1 C2 1.402(2) . ?
C1 C7 1.483(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.395(2) . ?
C7 C8 1.435(2) . ?
C8 O1 1.237(2) . ?
C8 C9 1.491(2) . ?
C9 C12 1.331(2) . ?
C9 C10 1.489(2) . ?
C10 C11 1.517(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.332(2) . ?
C12 C13 1.426(3) . ?
C12 H12 0.9300 . ?
C13 N1 1.141(3) . ?
C14 N2 1.464(2) . ?
C14 C15 1.506(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O2 1.420(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.426(2) . ?
C16 C17 1.505(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.466(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C6 C1 C2 118.52(15) . . ?
C6 C1 C7 120.22(15) . . ?
C2 C1 C7 121.04(15) . . ?
C3 C2 C1 120.17(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.17(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.93(17) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.52(19) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.68(18) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C11 C7 C8 108.94(14) . . ?
C11 C7 C1 130.57(15) . . ?
C8 C7 C1 120.33(14) . . ?
O1 C8 C7 129.12(16) . . ?
O1 C8 C9 123.07(16) . . ?
C7 C8 C9 107.81(14) . . ?
C12 C9 C10 128.70(16) . . ?
C12 C9 C8 122.64(17) . . ?
C10 C9 C8 108.67(14) . . ?
C9 C10 C11 102.74(13) . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
N2 C11 C7 130.02(14) . . ?
N2 C11 C10 118.48(14) . . ?
C7 C11 C10 111.47(14) . . ?
C9 C12 C13 123.16(18) . . ?
C9 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
N1 C13 C12 179.4(2) . . ?
N2 C14 C15 109.69(15) . . ?
N2 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O2 C15 C14 111.11(15) . . ?
O2 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
O2 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 C17 112.94(16) . . ?
O2 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
O2 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N2 C17 C16 109.31(15) . . ?
N2 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C15 O2 C16 110.98(13) . . ?
C11 N2 C14 123.85(14) . . ?
C11 N2 C17 124.81(14) . . ?
C14 N2 C17 111.23(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
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C1 C2 C3 175.64(16) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 -175.16(16) . . . . ?
C6 C1 C7 C11 -137.13(19) . . . . ?
C2 C1 C7 C11 48.3(3) . . . . ?
C6 C1 C7 C8 48.1(2) . . . . ?
C2 C1 C7 C8 -126.53(18) . . . . ?
C11 C7 C8 O1 176.83(19) . . . . ?
C1 C7 C8 O1 -7.4(3) . . . . ?
C11 C7 C8 C9 -4.02(19) . . . . ?
C1 C7 C8 C9 171.79(14) . . . . ?
O1 C8 C9 C12 -0.3(3) . . . . ?
C7 C8 C9 C12 -179.54(17) . . . . ?
O1 C8 C9 C10 179.43(18) . . . . ?
C7 C8 C9 C10 0.22(19) . . . . ?
C12 C9 C10 C11 -177.01(18) . . . . ?
C8 C9 C10 C11 3.26(18) . . . . ?
C8 C7 C11 N2 -171.31(17) . . . . ?
C1 C7 C11 N2 13.4(3) . . . . ?
C8 C7 C11 C10 6.4(2) . . . . ?
C1 C7 C11 C10 -168.89(16) . . . . ?
C9 C10 C11 N2 172.04(15) . . . . ?
C9 C10 C11 C7 -5.92(19) . . . . ?
C10 C9 C12 C13 1.8(3) . . . . ?
C8 C9 C12 C13 -178.48(17) . . . . ?
N2 C14 C15 O2 -57.9(2) . . . . ?
O2 C16 C17 N2 54.6(2) . . . . ?
C14 C15 O2 C16 57.6(2) . . . . ?
C17 C16 O2 C15 -56.7(2) . . . . ?
C7 C11 N2 C14 -172.82(17) . . . . ?
C10 C11 N2 C14 9.7(2) . . . . ?
C7 C11 N2 C17 11.4(3) . . . . ?
C10 C11 N2 C17 -166.17(16) . . . . ?
C15 C14 N2 C11 -119.58(18) . . . . ?
C15 C14 N2 C17 56.7(2) . . . . ?
C16 C17 N2 C11 121.63(18) . . . . ?
C16 C17 N2 C14 -54.6(2) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.065



