# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_KA905_0m
_database_code_depnum_ccdc_archive 'CCDC 2047320'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-08-09 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         ?
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40

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                   19.6210(13)
_cell_length_b                   7.3648(5)
_cell_length_c                   25.7732(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3724.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8794
_cell_measurement_theta_min      2.6095
_cell_measurement_theta_max      29.5035

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27104
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.609
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4237
_reflns_number_gt                2777
_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  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0466P)²+0.9964P] 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         4237
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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 0.60605(7) 0.3282(2) 0.41768(5) 0.0722(4) Uani 1 1 d . . . . .
O2 O 0.54438(7) 0.1931(2) 0.54504(5) 0.0636(4) Uani 1 1 d . . . . .
O3 O 0.53889(6) 0.10985(18) 0.62859(5) 0.0583(4) Uani 1 1 d . . . . .
N1 N 0.67268(8) 0.2469(2) 0.50699(5) 0.0460(4) Uani 1 1 d . . . . .
C1 C 0.66414(9) 0.4333(2) 0.34335(6) 0.0486(4) Uani 1 1 d . . . . .
C2 C 0.61228(11) 0.3814(3) 0.31037(7) 0.0602(5) Uani 1 1 d . . . . .
H2 H 0.577098 0.308776 0.322790 0.072 Uiso 1 1 calc R U . . .
C3 C 0.61205(12) 0.4361(3) 0.25907(8) 0.0699(6) Uani 1 1 d . . . . .
H3 H 0.577906 0.396128 0.236797 0.084 Uiso 1 1 calc R U . . .
C4 C 0.66209(13) 0.5490(3) 0.24111(8) 0.0699(6) Uani 1 1 d . . . . .
H4 H 0.661248 0.588334 0.206833 0.084 Uiso 1 1 calc R U . . .
C5 C 0.71333(12) 0.6042(3) 0.27338(8) 0.0657(6) Uani 1 1 d . . . . .
H5 H 0.746984 0.682065 0.261120 0.079 Uiso 1 1 calc R U . . .
C6 C 0.71522(10) 0.5444(2) 0.32423(7) 0.0555(5) Uani 1 1 d . . . . .
H6 H 0.751012 0.579102 0.345711 0.067 Uiso 1 1 calc R U . . .
C7 C 0.66186(10) 0.3700(2) 0.39875(7) 0.0507(4) Uani 1 1 d . . . . .
C8 C 0.72395(9) 0.3523(2) 0.42684(7) 0.0483(4) Uani 1 1 d . . . . .
H8 H 0.764428 0.384511 0.410466 0.058 Uiso 1 1 calc R U . . .
C9 C 0.72686(9) 0.2901(2) 0.47677(6) 0.0437(4) Uani 1 1 d . . . . .
C10 C 0.78726(8) 0.2534(2) 0.50816(6) 0.0443(4) Uani 1 1 d . . . . .
C11 C 0.85604(9) 0.2694(3) 0.49481(8) 0.0554(5) Uani 1 1 d . . . . .
H11 H 0.868744 0.312198 0.462275 0.066 Uiso 1 1 calc R U . . .
C12 C 0.90370(10) 0.2214(3) 0.53002(8) 0.0589(5) Uani 1 1 d . . . . .
H12 H 0.949547 0.230526 0.521237 0.071 Uiso 1 1 calc R U . . .
C13 C 0.88563(9) 0.1576(2) 0.57995(7) 0.0495(4) Uani 1 1 d . . . . .
C14 C 0.93634(10) 0.1081(3) 0.61605(9) 0.0616(5) Uani 1 1 d . . . . .
H14 H 0.982006 0.117660 0.606771 0.074 Uiso 1 1 calc R U . . .
C15 C 0.91978(10) 0.0466(3) 0.66407(8) 0.0640(5) Uani 1 1 d . . . . .
H15 H 0.953965 0.014814 0.687347 0.077 Uiso 1 1 calc R U . . .
C16 C 0.85186(10) 0.0312(3) 0.67846(8) 0.0597(5) Uani 1 1 d . . . . .
H16 H 0.840780 -0.011268 0.711378 0.072 Uiso 1 1 calc R U . . .
C17 C 0.80114(9) 0.0779(2) 0.64468(7) 0.0513(4) Uani 1 1 d . . . . .
H17 H 0.755942 0.067167 0.655112 0.062 Uiso 1 1 calc R U . . .
C18 C 0.81577(8) 0.1419(2) 0.59441(6) 0.0423(4) Uani 1 1 d . . . . .
C19 C 0.76655(8) 0.1914(2) 0.55628(6) 0.0398(4) Uani 1 1 d . . . . .
C20 C 0.69153(9) 0.1888(2) 0.55608(6) 0.0403(4) Uani 1 1 d . . . . .
C21 C 0.64608(8) 0.1437(2) 0.59285(6) 0.0437(4) Uani 1 1 d . . . . .
H21 H 0.662246 0.105220 0.624939 0.052 Uiso 1 1 calc R U . . .
C22 C 0.57295(9) 0.1522(2) 0.58489(7) 0.0473(4) Uani 1 1 d . . . . .
C23 C 0.46540(10) 0.1182(4) 0.62562(9) 0.0771(7) Uani 1 1 d . . . . .
H23A H 0.448242 0.018112 0.604942 0.093 Uiso 1 1 calc R U . . .
H23B H 0.451349 0.231028 0.609398 0.093 Uiso 1 1 calc R U . . .
C24 C 0.43796(12) 0.1074(4) 0.67878(10) 0.0906(8) Uani 1 1 d . . . . .
H24A H 0.389074 0.104747 0.677476 0.136 Uiso 1 1 calc R U . . .
H24B H 0.452577 0.211555 0.698239 0.136 Uiso 1 1 calc R U . . .
H24C H 0.454366 -0.000995 0.695254 0.136 Uiso 1 1 calc R U . . .
H1N H 0.6308(10) 0.257(3) 0.4983(7) 0.057(6) Uiso 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
O1 C7 1.238(2) . ?
O2 C22 1.208(2) . ?
O3 C22 1.346(2) . ?
O3 C23 1.445(2) . ?
N1 C9 1.356(2) . ?
N1 C20 1.386(2) . ?
N1 H1N 0.855(19) . ?
C1 C2 1.380(3) . ?
C1 C6 1.385(3) . ?
C1 C7 1.502(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.423(3) . ?
C8 C9 1.367(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.460(2) . ?
C10 C19 1.383(2) . ?
C10 C11 1.398(2) . ?
C11 C12 1.350(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.415(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.410(3) . ?
C13 C18 1.425(2) . ?
C14 C15 1.357(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.408(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.425(2) . ?
C19 C20 1.472(2) . ?
C20 C21 1.343(2) . ?
C21 C22 1.451(2) . ?
C21 H21 0.9300 . ?
C23 C24 1.474(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C22 O3 C23 116.17(15) . . ?
C9 N1 C20 112.82(15) . . ?
C9 N1 H1N 125.6(13) . . ?
C20 N1 H1N 121.6(13) . . ?
C2 C1 C6 118.57(17) . . ?
C2 C1 C7 118.53(17) . . ?
C6 C1 C7 122.89(17) . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.21(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.40(19) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 C8 122.28(17) . . ?
O1 C7 C1 118.55(17) . . ?
C8 C7 C1 119.10(16) . . ?
C9 C8 C7 123.04(17) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
N1 C9 C8 125.93(16) . . ?
N1 C9 C10 105.94(15) . . ?
C8 C9 C10 128.13(16) . . ?
C19 C10 C11 122.15(16) . . ?
C19 C10 C9 108.64(15) . . ?
C11 C10 C9 129.19(16) . . ?
C12 C11 C10 118.79(17) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 121.63(17) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 120.60(17) . . ?
C14 C13 C18 119.01(17) . . ?
C12 C13 C18 120.39(16) . . ?
C15 C14 C13 121.26(18) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.06(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.56(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.47(17) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 125.58(15) . . ?
C17 C18 C13 117.64(16) . . ?
C19 C18 C13 116.78(15) . . ?
C10 C19 C18 120.25(15) . . ?
C10 C19 C20 107.15(14) . . ?
C18 C19 C20 132.58(15) . . ?
C21 C20 N1 122.91(16) . . ?
C21 C20 C19 131.66(15) . . ?
N1 C20 C19 105.43(14) . . ?
C20 C21 C22 123.11(16) . . ?
C20 C21 H21 118.4 . . ?
C22 C21 H21 118.4 . . ?
O2 C22 O3 122.59(16) . . ?
O2 C22 C21 126.16(16) . . ?
O3 C22 C21 111.25(15) . . ?
O3 C23 C24 108.23(18) . . ?
O3 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
O3 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 1.3(3) . . . . ?
C7 C1 C2 C3 179.99(18) . . . . ?
C1 C2 C3 C4 -2.7(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C7 C1 C6 C5 -177.51(17) . . . . ?
C2 C1 C7 O1 -23.7(3) . . . . ?
C6 C1 C7 O1 154.95(19) . . . . ?
C2 C1 C7 C8 153.48(17) . . . . ?
C6 C1 C7 C8 -27.9(3) . . . . ?
O1 C7 C8 C9 -0.8(3) . . . . ?
C1 C7 C8 C9 -177.81(16) . . . . ?
C20 N1 C9 C8 -179.55(16) . . . . ?
C20 N1 C9 C10 1.44(19) . . . . ?
C7 C8 C9 N1 -3.7(3) . . . . ?
C7 C8 C9 C10 175.06(16) . . . . ?
N1 C9 C10 C19 -0.68(18) . . . . ?
C8 C9 C10 C19 -179.67(16) . . . . ?
N1 C9 C10 C11 177.70(17) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C19 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C12 -177.73(17) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 179.89(19) . . . . ?
C11 C12 C13 C18 0.1(3) . . . . ?
C12 C13 C14 C15 -179.97(18) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 179.06(17) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 0.3(2) . . . . ?
C12 C13 C18 C17 -179.90(16) . . . . ?
C14 C13 C18 C19 -179.17(16) . . . . ?
C12 C13 C18 C19 0.6(2) . . . . ?
C11 C10 C19 C18 0.3(2) . . . . ?
C9 C10 C19 C18 178.82(14) . . . . ?
C11 C10 C19 C20 -178.77(15) . . . . ?
C9 C10 C19 C20 -0.25(18) . . . . ?
C17 C18 C19 C10 179.74(16) . . . . ?
C13 C18 C19 C10 -0.8(2) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C13 C18 C19 C20 177.99(16) . . . . ?
C9 N1 C20 C21 178.16(15) . . . . ?
C9 N1 C20 C19 -1.59(18) . . . . ?
C10 C19 C20 C21 -178.64(17) . . . . ?
C18 C19 C20 C21 2.5(3) . . . . ?
C10 C19 C20 N1 1.07(17) . . . . ?
C18 C19 C20 N1 -177.83(16) . . . . ?
N1 C20 C21 C22 -0.3(3) . . . . ?
C19 C20 C21 C22 179.36(16) . . . . ?
C23 O3 C22 O2 -0.8(3) . . . . ?
C23 O3 C22 C21 178.52(16) . . . . ?
C20 C21 C22 O2 2.8(3) . . . . ?
C20 C21 C22 O3 -176.54(15) . . . . ?
C22 O3 C23 C24 -167.83(18) . . . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
