# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_KA918_0m
_database_code_depnum_ccdc_archive 'CCDC 2217042'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-01-04 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         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.5837(11)
_cell_length_b                   14.4099(13)
_cell_length_c                   12.4674(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.773(4)
_cell_angle_gamma                90
_cell_volume                     1901.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      29.9445

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS 2014/5'

_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            35526
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.160
_diffrn_reflns_theta_max         30.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5015
_reflns_number_gt                3575
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0560P)²+0.9995P] 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_number_reflns         5015
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1642
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.40909(16) 0.56606(11) 0.28263(14) 0.0344(4) Uani 1 1 d . . . . .
C2 C 0.51182(17) 0.55503(13) 0.21564(15) 0.0405(4) Uani 1 1 d . . . . .
H2 H 0.509170 0.509655 0.162613 0.049 Uiso 1 1 calc R U . . .
C3 C 0.61776(17) 0.61026(13) 0.22644(15) 0.0429(4) Uani 1 1 d . . . . .
C4 C 0.62133(17) 0.67617(13) 0.30764(16) 0.0433(4) Uani 1 1 d . . . . .
H4 H 0.692404 0.713664 0.315305 0.052 Uiso 1 1 calc R U . . .
C5 C 0.52129(16) 0.68771(11) 0.37802(14) 0.0360(4) Uani 1 1 d . . . . .
C6 C 0.41156(15) 0.63319(11) 0.36422(13) 0.0311(3) Uani 1 1 d . . . . .
C7 C 0.29524(15) 0.64890(11) 0.42646(12) 0.0302(3) Uani 1 1 d . . . . .
C8 C 0.21482(16) 0.72557(11) 0.42400(13) 0.0318(3) Uani 1 1 d . . . . .
C9 C 0.10956(16) 0.70423(12) 0.49234(13) 0.0358(4) Uani 1 1 d . . . . .
C10 C 0.13320(17) 0.61572(12) 0.53441(14) 0.0377(4) Uani 1 1 d . . . . .
C11 C -0.00179(19) 0.75028(15) 0.51995(17) 0.0504(5) Uani 1 1 d . . . . .
H11 H -0.020289 0.808856 0.492630 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0838(2) 0.70611(18) 0.5892(2) 0.0634(6) Uani 1 1 d . . . . .
H12 H -0.158122 0.735826 0.608431 0.076 Uiso 1 1 calc R U . . .
C13 C -0.0577(2) 0.61901(17) 0.63035(19) 0.0641(7) Uani 1 1 d . . . . .
H13 H -0.114913 0.591529 0.676570 0.077 Uiso 1 1 calc R U . . .
C14 C 0.0510(2) 0.57197(15) 0.60454(17) 0.0539(5) Uani 1 1 d . . . . .
H14 H 0.068695 0.513563 0.632692 0.065 Uiso 1 1 calc R U . . .
C15 C 0.53614(17) 0.75184(13) 0.47077(17) 0.0438(4) Uani 1 1 d . . . . .
C16 C 0.5818(2) 0.84139(16) 0.4574(2) 0.0698(7) Uani 1 1 d . . . . .
H16 H 0.598442 0.863618 0.389034 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6027(3) 0.8978(2) 0.5464(3) 0.0927(10) Uani 1 1 d . . . . .
H17 H 0.632809 0.957840 0.536773 0.111 Uiso 1 1 calc R U . . .
C18 C 0.5797(3) 0.8664(2) 0.6479(3) 0.0873(10) Uani 1 1 d . . . . .
H18 H 0.594864 0.904655 0.706793 0.105 Uiso 1 1 calc R U . . .
C19 C 0.5345(2) 0.7788(2) 0.6623(2) 0.0694(7) Uani 1 1 d . . . . .
H19 H 0.518051 0.757296 0.731046 0.083 Uiso 1 1 calc R U . . .
C20 C 0.51298(19) 0.72167(15) 0.57457(17) 0.0508(5) Uani 1 1 d . . . . .
H20 H 0.482420 0.661927 0.585329 0.061 Uiso 1 1 calc R U . . .
C21 C 0.3046(2) 0.49583(13) 0.52245(18) 0.0506(5) Uani 1 1 d . . . . .
H21A H 0.243060 0.447117 0.516219 0.076 Uiso 1 1 calc R U . . .
H21B H 0.335353 0.499101 0.595145 0.076 Uiso 1 1 calc R U . . .
H21C H 0.373678 0.483187 0.475524 0.076 Uiso 1 1 calc R U . . .
C22 C 0.23735(18) 0.80723(12) 0.36412(14) 0.0386(4) Uani 1 1 d . . . . .
H22 H 0.308556 0.808756 0.321251 0.046 Uiso 1 1 calc R U . . .
C23 C 0.7288(2) 0.59617(19) 0.1536(2) 0.0650(6) Uani 1 1 d . . . . .
H23A H 0.699846 0.570069 0.086768 0.097 Uiso 1 1 calc R U . . .
H23B H 0.788286 0.554694 0.187077 0.097 Uiso 1 1 calc R U . . .
H23C H 0.768813 0.654786 0.140440 0.097 Uiso 1 1 calc R U . . .
H2O H 0.316(3) 0.465(2) 0.221(2) 0.085(9) Uiso 1 1 d . . . . .
N1 N 0.24659(14) 0.58380(9) 0.49287(11) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.16905(15) 0.87634(9) 0.36496(12) 0.0569(4) Uani 1 1 d . . . . .
O2 O 0.30331(12) 0.51353(9) 0.27269(11) 0.0448(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 O2 1.356(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.404(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 C23 1.509(3) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(2) . ?
C5 C15 1.487(3) . ?
C6 C7 1.481(2) . ?
C7 N1 1.357(2) . ?
C7 C8 1.395(2) . ?
C8 C22 1.415(2) . ?
C8 C9 1.445(2) . ?
C9 C11 1.400(3) . ?
C9 C10 1.400(2) . ?
C10 N1 1.392(2) . ?
C10 C14 1.393(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.389(3) . ?
C15 C20 1.390(3) . ?
C16 C17 1.390(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N1 1.454(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O1 1.231(2) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O2 H2O 0.96(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
O2 C1 C2 122.23(16) . . ?
O2 C1 C6 117.28(15) . . ?
C2 C1 C6 120.50(16) . . ?
C3 C2 C1 121.12(17) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.66(17) . . ?
C2 C3 C23 120.13(19) . . ?
C4 C3 C23 121.17(18) . . ?
C3 C4 C5 121.81(17) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 119.20(16) . . ?
C4 C5 C15 119.36(16) . . ?
C6 C5 C15 121.28(16) . . ?
C1 C6 C5 118.64(15) . . ?
C1 C6 C7 118.52(14) . . ?
C5 C6 C7 122.65(15) . . ?
N1 C7 C8 108.93(14) . . ?
N1 C7 C6 122.59(14) . . ?
C8 C7 C6 128.37(14) . . ?
C7 C8 C22 124.26(15) . . ?
C7 C8 C9 107.08(14) . . ?
C22 C8 C9 128.66(15) . . ?
C11 C9 C10 119.12(17) . . ?
C11 C9 C8 134.64(17) . . ?
C10 C9 C8 106.23(15) . . ?
N1 C10 C14 129.29(18) . . ?
N1 C10 C9 108.20(14) . . ?
C14 C10 C9 122.51(18) . . ?
C12 C11 C9 118.1(2) . . ?
C12 C11 H11 120.9 . . ?
C9 C11 H11 120.9 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C10 117.1(2) . . ?
C13 C14 H14 121.5 . . ?
C10 C14 H14 121.5 . . ?
C16 C15 C20 117.9(2) . . ?
C16 C15 C5 121.2(2) . . ?
C20 C15 C5 120.76(17) . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 121.3(2) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 C8 124.40(17) . . ?
O1 C22 H22 117.8 . . ?
C8 C22 H22 117.8 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 N1 C10 109.56(14) . . ?
C7 N1 C21 126.51(15) . . ?
C10 N1 C21 123.85(15) . . ?
C1 O2 H2O 109.9(17) . . ?

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
O2 C1 C2 C3 179.09(17) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C23 179.27(18) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C23 C3 C4 C5 -177.67(18) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
C3 C4 C5 C15 173.18(17) . . . . ?
O2 C1 C6 C5 178.74(15) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
O2 C1 C6 C7 -6.1(2) . . . . ?
C2 C1 C6 C7 173.92(15) . . . . ?
C4 C5 C6 C1 2.8(2) . . . . ?
C15 C5 C6 C1 -172.54(16) . . . . ?
C4 C5 C6 C7 -172.21(15) . . . . ?
C15 C5 C6 C7 12.5(2) . . . . ?
C1 C6 C7 N1 66.5(2) . . . . ?
C5 C6 C7 N1 -118.48(18) . . . . ?
C1 C6 C7 C8 -109.34(19) . . . . ?
C5 C6 C7 C8 65.6(2) . . . . ?
N1 C7 C8 C22 178.95(16) . . . . ?
C6 C7 C8 C22 -4.7(3) . . . . ?
N1 C7 C8 C9 -1.01(18) . . . . ?
C6 C7 C8 C9 175.31(16) . . . . ?
C7 C8 C9 C11 -177.6(2) . . . . ?
C22 C8 C9 C11 2.4(3) . . . . ?
C7 C8 C9 C10 1.05(19) . . . . ?
C22 C8 C9 C10 -178.91(17) . . . . ?
C11 C9 C10 N1 178.19(16) . . . . ?
C8 C9 C10 N1 -0.71(19) . . . . ?
C11 C9 C10 C14 -1.1(3) . . . . ?
C8 C9 C10 C14 179.96(17) . . . . ?
C10 C9 C11 C12 0.6(3) . . . . ?
C8 C9 C11 C12 179.1(2) . . . . ?
C9 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C10 -0.5(4) . . . . ?
N1 C10 C14 C13 -178.13(19) . . . . ?
C9 C10 C14 C13 1.0(3) . . . . ?
C4 C5 C15 C16 49.2(3) . . . . ?
C6 C5 C15 C16 -135.5(2) . . . . ?
C4 C5 C15 C20 -126.2(2) . . . . ?
C6 C5 C15 C20 49.1(2) . . . . ?
C20 C15 C16 C17 -0.1(4) . . . . ?
C5 C15 C16 C17 -175.7(2) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C5 C15 C20 C19 175.66(19) . . . . ?
C7 C8 C22 O1 -177.12(18) . . . . ?
C9 C8 C22 O1 2.8(3) . . . . ?
C8 C7 N1 C10 0.58(19) . . . . ?
C6 C7 N1 C10 -176.00(15) . . . . ?
C8 C7 N1 C21 -176.31(17) . . . . ?
C6 C7 N1 C21 7.1(3) . . . . ?
C14 C10 N1 C7 179.37(19) . . . . ?
C9 C10 N1 C7 0.11(19) . . . . ?
C14 C10 N1 C21 -3.6(3) . . . . ?
C9 C10 N1 C21 177.09(17) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053

