# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_KB1011_0m
_database_code_depnum_ccdc_archive 'CCDC 2370423'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-07-13 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.5854(7)
_cell_length_b                   17.6825(13)
_cell_length_c                   21.0981(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3576.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8514
_cell_measurement_theta_min      2.498
_cell_measurement_theta_max      24.292

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30918
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.603
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4088
_reflns_number_gt                2403
_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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0696P)²+0.5893P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0065(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4088
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.2088(2) 0.61861(10) 0.27473(9) 0.0692(5) Uani 1 1 d . . . . .
C2 C 0.31684(18) 0.56786(9) 0.29495(9) 0.0591(5) Uani 1 1 d . . . . .
C3 C 0.39050(18) 0.52399(10) 0.25640(9) 0.0621(5) Uani 1 1 d . . . . .
H3 H 0.378428 0.522320 0.212687 0.075 Uiso 1 1 calc R U . . .
C4 C 0.49302(18) 0.47856(10) 0.29097(9) 0.0616(5) Uani 1 1 d . . . . .
H4 H 0.586479 0.471385 0.273121 0.074 Uiso 1 1 calc R U . . .
C5 C 0.43684(16) 0.42168(9) 0.33977(8) 0.0546(4) Uani 1 1 d . . . . .
C6 C 0.47751(17) 0.50219(10) 0.35944(8) 0.0600(5) Uani 1 1 d . . . . .
C7 C 0.35501(19) 0.55881(9) 0.36451(9) 0.0625(5) Uani 1 1 d . . . . .
C8 C 0.3980(3) 0.63392(11) 0.39480(12) 0.0936(7) Uani 1 1 d . . . . .
H8A H 0.478845 0.653415 0.373477 0.140 Uiso 1 1 calc R U . . .
H8B H 0.419372 0.625939 0.438751 0.140 Uiso 1 1 calc R U . . .
H8C H 0.322804 0.669504 0.391179 0.140 Uiso 1 1 calc R U . . .
C9 C 0.2347(2) 0.52131(10) 0.40100(9) 0.0676(5) Uani 1 1 d . . . . .
H9A H 0.264400 0.511428 0.444165 0.081 Uiso 1 1 calc R U . . .
H9B H 0.156236 0.555870 0.402656 0.081 Uiso 1 1 calc R U . . .
C10 C 0.18875(17) 0.44836(9) 0.37087(8) 0.0565(4) Uani 1 1 d . . . . .
C11 C 0.28563(15) 0.40189(9) 0.34062(8) 0.0518(4) Uani 1 1 d . . . . .
C12 C 0.24129(18) 0.33634(9) 0.31009(9) 0.0622(5) Uani 1 1 d . . . . .
H12 H 0.305972 0.306402 0.288879 0.075 Uiso 1 1 calc R U . . .
C13 C 0.1038(2) 0.31532(11) 0.31086(11) 0.0754(6) Uani 1 1 d . . . . .
H13 H 0.075388 0.271330 0.290427 0.091 Uiso 1 1 calc R U . . .
C14 C 0.0086(2) 0.35937(13) 0.34183(11) 0.0827(7) Uani 1 1 d . . . . .
H14 H -0.084500 0.344654 0.343242 0.099 Uiso 1 1 calc R U . . .
C15 C 0.04981(18) 0.42577(12) 0.37114(10) 0.0725(6) Uani 1 1 d . . . . .
H15 H -0.016451 0.455725 0.391302 0.087 Uiso 1 1 calc R U . . .
C16 C 0.54403(18) 0.36228(10) 0.35736(9) 0.0650(5) Uani 1 1 d . . . . .
C17 C 0.50755(18) 0.29872(10) 0.40043(10) 0.0645(5) Uani 1 1 d . . . . .
C18 C 0.4118(2) 0.30533(11) 0.44909(10) 0.0745(6) Uani 1 1 d . . . . .
H18 H 0.361057 0.349814 0.453802 0.089 Uiso 1 1 calc R U . . .
C19 C 0.3911(3) 0.24606(15) 0.49079(12) 0.0996(8) Uani 1 1 d . . . . .
H19 H 0.328313 0.251356 0.524112 0.120 Uiso 1 1 calc R U . . .
C20 C 0.4618(4) 0.18028(17) 0.48336(17) 0.1184(10) Uani 1 1 d . . . . .
H20 H 0.446155 0.140443 0.511253 0.142 Uiso 1 1 calc R U . . .
C21 C 0.5560(3) 0.17204(14) 0.43508(19) 0.1176(11) Uani 1 1 d . . . . .
H21 H 0.603740 0.126654 0.430116 0.141 Uiso 1 1 calc R U . . .
C22 C 0.5800(2) 0.23133(12) 0.39368(13) 0.0919(7) Uani 1 1 d . . . . .
H22 H 0.644975 0.225964 0.361240 0.110 Uiso 1 1 calc R U . . .
C23 C 0.5975(2) 0.51256(12) 0.40004(11) 0.0794(6) Uani 1 1 d . . . . .
N1 N 0.1251(2) 0.66019(10) 0.25894(11) 0.0978(6) Uani 1 1 d . . . . .
N2 N 0.6910(2) 0.52176(13) 0.43221(12) 0.1190(8) Uani 1 1 d . . . . .
O1 O 0.66223(14) 0.36845(10) 0.33752(8) 0.1021(6) 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 N1 1.138(2) . ?
C1 C2 1.435(3) . ?
C2 C3 1.327(2) . ?
C2 C7 1.521(3) . ?
C3 C4 1.464(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.511(3) . ?
C4 C5 1.537(2) . ?
C4 H4 0.9800 . ?
C5 C11 1.491(2) . ?
C5 C16 1.515(2) . ?
C5 C6 1.533(2) . ?
C6 C23 1.446(3) . ?
C6 C7 1.547(3) . ?
C7 C8 1.530(3) . ?
C7 C9 1.537(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.504(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.390(2) . ?
C10 C11 1.395(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O1 1.213(2) . ?
C16 C17 1.487(3) . ?
C17 C18 1.382(3) . ?
C17 C22 1.387(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.355(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 N2 1.136(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
N1 C1 C2 178.5(2) . . ?
C3 C2 C1 124.55(17) . . ?
C3 C2 C7 113.69(16) . . ?
C1 C2 C7 121.75(16) . . ?
C2 C3 C4 111.87(16) . . ?
C2 C3 H3 124.1 . . ?
C4 C3 H3 124.1 . . ?
C3 C4 C6 104.98(14) . . ?
C3 C4 C5 117.24(14) . . ?
C6 C4 C5 60.40(11) . . ?
C3 C4 H4 119.5 . . ?
C6 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C11 C5 C16 119.57(14) . . ?
C11 C5 C6 117.50(14) . . ?
C16 C5 C6 113.88(14) . . ?
C11 C5 C4 120.15(14) . . ?
C16 C5 C4 112.34(14) . . ?
C6 C5 C4 58.97(11) . . ?
C23 C6 C4 121.55(17) . . ?
C23 C6 C5 118.71(16) . . ?
C4 C6 C5 60.63(11) . . ?
C23 C6 C7 118.74(16) . . ?
C4 C6 C7 108.65(14) . . ?
C5 C6 C7 115.26(13) . . ?
C2 C7 C8 112.12(15) . . ?
C2 C7 C9 110.38(15) . . ?
C8 C7 C9 111.55(17) . . ?
C2 C7 C6 100.60(14) . . ?
C8 C7 C6 112.71(16) . . ?
C9 C7 C6 108.95(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 112.23(14) . . ?
C10 C9 H9A 109.2 . . ?
C7 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C7 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C15 C10 C11 118.06(17) . . ?
C15 C10 C9 121.69(17) . . ?
C11 C10 C9 120.23(15) . . ?
C12 C11 C10 119.93(15) . . ?
C12 C11 C5 119.11(15) . . ?
C10 C11 C5 120.96(14) . . ?
C13 C12 C11 120.94(18) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.44(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 121.00(18) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O1 C16 C17 119.90(16) . . ?
O1 C16 C5 119.11(17) . . ?
C17 C16 C5 120.94(15) . . ?
C18 C17 C22 118.8(2) . . ?
C18 C17 C16 123.10(16) . . ?
C22 C17 C16 117.96(19) . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
N2 C23 C6 179.0(3) . . ?

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
C1 C2 C3 C4 179.99(15) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C2 C3 C4 C6 -1.88(18) . . . . ?
C2 C3 C4 C5 62.19(19) . . . . ?
C3 C4 C5 C11 13.5(2) . . . . ?
C6 C4 C5 C11 105.89(17) . . . . ?
C3 C4 C5 C16 162.32(15) . . . . ?
C6 C4 C5 C16 -105.28(15) . . . . ?
C3 C4 C5 C6 -92.40(17) . . . . ?
C3 C4 C6 C23 -139.33(17) . . . . ?
C5 C4 C6 C23 107.53(19) . . . . ?
C3 C4 C6 C5 113.13(14) . . . . ?
C3 C4 C6 C7 4.06(17) . . . . ?
C5 C4 C6 C7 -109.07(14) . . . . ?
C11 C5 C6 C23 137.55(17) . . . . ?
C16 C5 C6 C23 -9.5(2) . . . . ?
C4 C5 C6 C23 -112.10(19) . . . . ?
C11 C5 C6 C4 -110.35(16) . . . . ?
C16 C5 C6 C4 102.63(16) . . . . ?
C11 C5 C6 C7 -12.3(2) . . . . ?
C16 C5 C6 C7 -159.31(15) . . . . ?
C4 C5 C6 C7 98.06(16) . . . . ?
C3 C2 C7 C8 123.52(19) . . . . ?
C1 C2 C7 C8 -57.6(2) . . . . ?
C3 C2 C7 C9 -111.45(16) . . . . ?
C1 C2 C7 C9 67.44(19) . . . . ?
C3 C2 C7 C6 3.51(18) . . . . ?
C1 C2 C7 C6 -177.59(15) . . . . ?
C23 C6 C7 C2 140.12(16) . . . . ?
C4 C6 C7 C2 -4.46(16) . . . . ?
C5 C6 C7 C2 -70.06(17) . . . . ?
C23 C6 C7 C8 20.5(2) . . . . ?
C4 C6 C7 C8 -124.04(17) . . . . ?
C5 C6 C7 C8 170.36(17) . . . . ?
C23 C6 C7 C9 -103.85(19) . . . . ?
C4 C6 C7 C9 111.57(16) . . . . ?
C5 C6 C7 C9 46.0(2) . . . . ?
C2 C7 C9 C10 53.20(19) . . . . ?
C8 C7 C9 C10 178.55(16) . . . . ?
C6 C7 C9 C10 -56.38(19) . . . . ?
C7 C9 C10 C15 -145.08(16) . . . . ?
C7 C9 C10 C11 33.7(2) . . . . ?
C15 C10 C11 C12 2.1(2) . . . . ?
C9 C10 C11 C12 -176.79(16) . . . . ?
C15 C10 C11 C5 -178.58(15) . . . . ?
C9 C10 C11 C5 2.6(2) . . . . ?
C16 C5 C11 C12 -49.2(2) . . . . ?
C6 C5 C11 C12 165.73(15) . . . . ?
C4 C5 C11 C12 97.42(19) . . . . ?
C16 C5 C11 C10 131.46(17) . . . . ?
C6 C5 C11 C10 -13.6(2) . . . . ?
C4 C5 C11 C10 -81.9(2) . . . . ?
C10 C11 C12 C13 -2.0(3) . . . . ?
C5 C11 C12 C13 178.65(16) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C10 -1.3(3) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C9 C10 C15 C14 178.38(17) . . . . ?
C11 C5 C16 O1 155.82(18) . . . . ?
C6 C5 C16 O1 -57.9(2) . . . . ?
C4 C5 C16 O1 6.8(2) . . . . ?
C11 C5 C16 C17 -26.6(2) . . . . ?
C6 C5 C16 C17 119.65(18) . . . . ?
C4 C5 C16 C17 -175.66(15) . . . . ?
O1 C16 C17 C18 145.3(2) . . . . ?
C5 C16 C17 C18 -32.2(3) . . . . ?
O1 C16 C17 C22 -30.5(3) . . . . ?
C5 C16 C17 C22 152.01(18) . . . . ?
C22 C17 C18 C19 1.2(3) . . . . ?
C16 C17 C18 C19 -174.55(19) . . . . ?
C17 C18 C19 C20 -1.7(3) . . . . ?
C18 C19 C20 C21 1.0(4) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C17 -0.9(4) . . . . ?
C18 C17 C22 C21 0.1(3) . . . . ?
C16 C17 C22 C21 176.1(2) . . . . ?

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.032



