# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_KA640_0m
_database_code_depnum_ccdc_archive 'CCDC 1912875'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2020-04-13 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         'C24 H23 N O'
_chemical_formula_sum            'C24 H23 N O'
_chemical_formula_weight         341.43

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.1269(7)
_cell_length_b                   9.0770(12)
_cell_length_c                   17.366(2)
_cell_angle_alpha                79.554(4)
_cell_angle_beta                 84.737(4)
_cell_angle_gamma                81.243(5)
_cell_volume                     936.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8290
_cell_measurement_theta_min      2.3905
_cell_measurement_theta_max      30.250

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6020
_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_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20789
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.304
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4289
_reflns_number_gt                3140
_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 2014/5 (Sheldrick, 2014)'
_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)+(0.1000P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4289
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 0.3466(2) 0.42919(16) 0.80041(8) 0.0440(3) Uani 1 1 d . . . . .
H1A H 0.226501 0.381267 0.787726 0.053 Uiso 1 1 calc R U . . .
H1B H 0.324387 0.438543 0.855438 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5617(2) 0.33076(15) 0.78736(8) 0.0403(3) Uani 1 1 d . . . . .
C3 C 0.6219(3) 0.20355(17) 0.84313(9) 0.0535(4) Uani 1 1 d . . . . .
H3 H 0.528071 0.181941 0.887677 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8172(3) 0.10892(18) 0.83383(9) 0.0598(5) Uani 1 1 d . . . . .
H4 H 0.855048 0.024624 0.871795 0.072 Uiso 1 1 calc R U . . .
C5 C 0.9554(3) 0.14027(18) 0.76804(10) 0.0562(4) Uani 1 1 d . . . . .
H5 H 1.087586 0.076935 0.761413 0.067 Uiso 1 1 calc R U . . .
C6 C 0.8993(2) 0.26563(17) 0.71144(9) 0.0461(4) Uani 1 1 d . . . . .
H6 H 0.994359 0.285185 0.667033 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7015(2) 0.36369(14) 0.71988(7) 0.0364(3) Uani 1 1 d . . . . .
C8 C 0.6327(2) 0.49586(14) 0.65908(7) 0.0340(3) Uani 1 1 d . . . . .
C9 C 0.3960(2) 0.56722(15) 0.67036(7) 0.0363(3) Uani 1 1 d . . . . .
H9A H 0.375176 0.667001 0.638344 0.044 Uiso 1 1 calc R U . . .
H9B H 0.298426 0.506257 0.653497 0.044 Uiso 1 1 calc R U . . .
C10 C 0.1190(2) 0.66711(16) 0.76176(8) 0.0424(3) Uani 1 1 d . . . . .
H10A H 0.009522 0.613171 0.746404 0.051 Uiso 1 1 calc R U . . .
H10B H 0.114712 0.763798 0.726883 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0603(2) 0.69394(16) 0.84500(8) 0.0417(3) Uani 1 1 d . . . . .
C12 C -0.1359(3) 0.65676(19) 0.88434(10) 0.0573(4) Uani 1 1 d . . . . .
H12 H -0.232495 0.614128 0.859420 0.069 Uiso 1 1 calc R U . . .
C13 C -0.1899(3) 0.6824(2) 0.96057(10) 0.0726(6) Uani 1 1 d . . . . .
H13 H -0.322073 0.656586 0.986429 0.087 Uiso 1 1 calc R U . . .
C14 C -0.0498(3) 0.7455(2) 0.99791(10) 0.0710(5) Uani 1 1 d . . . . .
H14 H -0.086566 0.762753 1.048979 0.085 Uiso 1 1 calc R U . . .
C15 C 0.1452(3) 0.7830(2) 0.95971(10) 0.0660(5) Uani 1 1 d . . . . .
H15 H 0.241268 0.825383 0.985009 0.079 Uiso 1 1 calc R U . . .
C16 C 0.1993(3) 0.75795(19) 0.88341(9) 0.0537(4) Uani 1 1 d . . . . .
H16 H 0.331270 0.784661 0.857760 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7706(2) 0.54974(15) 0.59989(7) 0.0386(3) Uani 1 1 d . . . . .
H17 H 0.915769 0.501469 0.599958 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7213(2) 0.67581(15) 0.53465(7) 0.0358(3) Uani 1 1 d . . . . .
C19 C 0.8751(2) 0.77728(17) 0.50942(8) 0.0435(3) Uani 1 1 d . . . . .
H19 H 1.008037 0.762202 0.533540 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8342(2) 0.89824(17) 0.45001(8) 0.0445(4) Uani 1 1 d . . . . .
H20 H 0.937476 0.965108 0.435286 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6394(2) 0.92116(15) 0.41183(7) 0.0374(3) Uani 1 1 d . . . . .
C22 C 0.4879(2) 0.82005(15) 0.43329(8) 0.0377(3) Uani 1 1 d . . . . .
H22 H 0.358999 0.832435 0.407006 0.045 Uiso 1 1 calc R U . . .
C23 C 0.5300(2) 0.70001(15) 0.49441(7) 0.0374(3) Uani 1 1 d . . . . .
H23 H 0.426359 0.633378 0.508932 0.045 Uiso 1 1 calc R U . . .
C24 C 0.4204(3) 1.0726(2) 0.31179(9) 0.0583(4) Uani 1 1 d . . . . .
H24A H 0.422728 1.163442 0.273684 0.087 Uiso 1 1 calc R U . . .
H24B H 0.292965 1.084251 0.347838 0.087 Uiso 1 1 calc R U . . .
H24C H 0.413613 0.989051 0.285632 0.087 Uiso 1 1 calc R U . . .
N1 N 0.33924(17) 0.57974(12) 0.75299(6) 0.0362(3) Uani 1 1 d . . . . .
O1 O 0.61504(17) 1.04480(12) 0.35346(6) 0.0522(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 N1 1.4586(16) . ?
C1 C2 1.4989(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.3920(18) . ?
C2 C7 1.4010(19) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.4031(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.4832(17) . ?
C8 C17 1.3390(18) . ?
C8 C9 1.5065(18) . ?
C9 N1 1.4658(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.4674(17) . ?
C10 C11 1.5113(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.380(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.4737(18) . ?
C17 H17 0.9300 . ?
C18 C23 1.3879(18) . ?
C18 C19 1.4039(19) . ?
C19 C20 1.3733(19) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9300 . ?
C21 O1 1.3688(15) . ?
C21 C22 1.3838(18) . ?
C22 C23 1.3877(17) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O1 1.4178(18) . ?
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
N1 C1 C2 112.44(11) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C7 119.62(13) . . ?
C3 C2 C1 119.14(13) . . ?
C7 C2 C1 121.24(12) . . ?
C4 C3 C2 121.49(15) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.35(14) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.41(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 121.16(14) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 117.98(12) . . ?
C2 C7 C8 119.47(12) . . ?
C6 C7 C8 122.51(12) . . ?
C17 C8 C7 122.94(12) . . ?
C17 C8 C9 122.55(11) . . ?
C7 C8 C9 114.49(11) . . ?
N1 C9 C8 110.55(9) . . ?
N1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C11 112.15(10) . . ?
N1 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C16 C11 C12 118.25(14) . . ?
C16 C11 C10 120.91(12) . . ?
C12 C11 C10 120.83(14) . . ?
C11 C12 C13 120.69(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.32(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.70(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.10(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.93(15) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C8 C17 C18 128.23(12) . . ?
C8 C17 H17 115.9 . . ?
C18 C17 H17 115.9 . . ?
C23 C18 C19 116.74(12) . . ?
C23 C18 C17 123.65(12) . . ?
C19 C18 C17 119.60(12) . . ?
C20 C19 C18 121.62(12) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.29(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
O1 C21 C22 124.81(12) . . ?
O1 C21 C20 115.63(12) . . ?
C22 C21 C20 119.55(12) . . ?
C21 C22 C23 119.38(12) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C18 122.36(12) . . ?
C22 C23 H23 118.8 . . ?
C18 C23 H23 118.8 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C9 109.82(10) . . ?
C1 N1 C10 110.61(10) . . ?
C9 N1 C10 110.11(9) . . ?
C21 O1 C24 118.05(11) . . ?

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
N1 C1 C2 C3 160.97(13) . . . . ?
N1 C1 C2 C7 -19.68(18) . . . . ?
C7 C2 C3 C4 0.3(2) . . . . ?
C1 C2 C3 C4 179.70(14) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C3 C2 C7 C6 -0.13(19) . . . . ?
C1 C2 C7 C6 -179.47(12) . . . . ?
C3 C2 C7 C8 177.59(12) . . . . ?
C1 C2 C7 C8 -1.76(19) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C5 C6 C7 C8 -177.81(12) . . . . ?
C2 C7 C8 C17 168.48(13) . . . . ?
C6 C7 C8 C17 -13.91(19) . . . . ?
C2 C7 C8 C9 -10.13(17) . . . . ?
C6 C7 C8 C9 167.47(12) . . . . ?
C17 C8 C9 N1 -135.44(13) . . . . ?
C7 C8 C9 N1 43.19(14) . . . . ?
N1 C10 C11 C16 53.60(17) . . . . ?
N1 C10 C11 C12 -127.25(14) . . . . ?
C16 C11 C12 C13 -0.4(2) . . . . ?
C10 C11 C12 C13 -179.60(15) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
C10 C11 C16 C15 179.80(14) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C7 C8 C17 C18 177.65(11) . . . . ?
C9 C8 C17 C18 -3.8(2) . . . . ?
C8 C17 C18 C23 -41.7(2) . . . . ?
C8 C17 C18 C19 139.56(15) . . . . ?
C23 C18 C19 C20 2.6(2) . . . . ?
C17 C18 C19 C20 -178.57(12) . . . . ?
C18 C19 C20 C21 -1.5(2) . . . . ?
C19 C20 C21 O1 -179.90(12) . . . . ?
C19 C20 C21 C22 -0.9(2) . . . . ?
O1 C21 C22 C23 -179.03(12) . . . . ?
C20 C21 C22 C23 2.1(2) . . . . ?
C21 C22 C23 C18 -0.9(2) . . . . ?
C19 C18 C23 C22 -1.4(2) . . . . ?
C17 C18 C23 C22 179.83(12) . . . . ?
C2 C1 N1 C9 52.77(14) . . . . ?
C2 C1 N1 C10 174.51(11) . . . . ?
C8 C9 N1 C1 -65.43(13) . . . . ?
C8 C9 N1 C10 172.53(10) . . . . ?
C11 C10 N1 C1 63.00(15) . . . . ?
C11 C10 N1 C9 -175.43(11) . . . . ?
C22 C21 O1 C24 0.3(2) . . . . ?
C20 C21 O1 C24 179.22(13) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039

