# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_KB100_0m
_database_code_depnum_ccdc_archive 'CCDC 2149875'
loop_
_audit_author_name
_audit_author_address
'Shaik Anwar'
;Vignans Foundation for Science Technology and research
India
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2023-02-06 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         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   10.0111(10)
_cell_length_b                   11.7592(12)
_cell_length_c                   13.0970(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1541.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.327
_cell_measurement_theta_max      29.783

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6725
_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      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            28119
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         27.486
_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 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3504
_reflns_number_gt                3158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.992

_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    ?
_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)+(0.0528P)²+0.1574P] 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_abs_structure_details 
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3504
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O1 O 0.85416(19) 0.39417(13) 0.42643(16) 0.0542(4) Uani 1 1 d . . . . .
O2 O 1.0303(3) 0.5631(2) 0.64790(18) 0.0946(8) Uani 1 1 d . . . . .
O3 O 1.0937(4) 0.4285(2) 0.5552(3) 0.1292(14) Uani 1 1 d . . . . .
N1 N 1.0351(2) 0.51519(16) 0.56690(18) 0.0521(5) Uani 1 1 d . . . . .
C1 C 0.3995(3) 0.4974(3) 0.6540(2) 0.0640(8) Uani 1 1 d . . . . .
H1 H 0.327976 0.446936 0.652988 0.077 Uiso 1 1 calc R U . . .
C2 C 0.3928(3) 0.5918(3) 0.7151(3) 0.0689(8) Uani 1 1 d . . . . .
H2 H 0.317649 0.604564 0.755211 0.083 Uiso 1 1 calc R U . . .
C3 C 0.4978(3) 0.6678(3) 0.7170(2) 0.0632(7) Uani 1 1 d . . . . .
H3 H 0.493797 0.731807 0.758568 0.076 Uiso 1 1 calc R U . . .
C4 C 0.6092(2) 0.6484(2) 0.65658(19) 0.0493(5) Uani 1 1 d . . . . .
H4 H 0.679329 0.700279 0.657743 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6183(2) 0.55280(18) 0.59421(17) 0.0400(4) Uani 1 1 d . . . . .
C6 C 0.5099(2) 0.4753(2) 0.5936(2) 0.0491(6) Uani 1 1 d . . . . .
C7 C 0.5163(3) 0.3749(2) 0.5232(2) 0.0608(7) Uani 1 1 d . . . . .
H7A H 0.480897 0.396547 0.457091 0.073 Uiso 1 1 calc R U . . .
H7B H 0.460340 0.314621 0.550191 0.073 Uiso 1 1 calc R U . . .
C8 C 0.6571(3) 0.32998(19) 0.5095(2) 0.0557(6) Uani 1 1 d . . . . .
H8A H 0.685197 0.290670 0.571017 0.067 Uiso 1 1 calc R U . . .
H8B H 0.659278 0.276203 0.453398 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7508(2) 0.42680(17) 0.48788(18) 0.0430(5) Uani 1 1 d . . . . .
C10 C 0.7340(2) 0.53064(16) 0.52829(15) 0.0364(4) Uani 1 1 d . . . . .
C11 C 0.83452(19) 0.62410(15) 0.50889(16) 0.0345(4) Uani 1 1 d . . . . .
H11 H 0.850011 0.664340 0.573343 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9665(2) 0.56988(18) 0.47536(18) 0.0409(5) Uani 1 1 d . . . . .
H12 H 1.024827 0.629418 0.447909 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9443(3) 0.4814(2) 0.3940(2) 0.0513(6) Uani 1 1 d . . . . .
H13A H 0.908697 0.517859 0.333356 0.062 Uiso 1 1 calc R U . . .
H13B H 1.029297 0.447237 0.376016 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7896(2) 0.71112(16) 0.42915(16) 0.0347(4) Uani 1 1 d . . . . .
C15 C 0.6914(2) 0.68731(18) 0.35799(18) 0.0447(5) Uani 1 1 d . . . . .
H15 H 0.649259 0.616833 0.358885 0.054 Uiso 1 1 calc R U . . .
C16 C 0.6550(3) 0.7675(2) 0.28518(19) 0.0542(6) Uani 1 1 d . . . . .
H16 H 0.588855 0.750245 0.237757 0.065 Uiso 1 1 calc R U . . .
C17 C 0.7162(3) 0.8723(2) 0.2829(2) 0.0542(6) Uani 1 1 d . . . . .
H17 H 0.692935 0.925395 0.233379 0.065 Uiso 1 1 calc R U . . .
C18 C 0.8116(3) 0.8975(2) 0.3540(3) 0.0580(6) Uani 1 1 d . . . . .
H18 H 0.852357 0.968527 0.353446 0.070 Uiso 1 1 calc R U . . .
C19 C 0.8479(2) 0.81826(18) 0.4268(2) 0.0480(5) Uani 1 1 d . . . . .
H19 H 0.912517 0.836969 0.475026 0.058 Uiso 1 1 calc R U . . .


_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 C9 1.366(3) . ?
O1 C13 1.431(3) . ?
O2 N1 1.202(3) . ?
O3 N1 1.186(3) . ?
N1 C12 1.524(3) . ?
C1 C2 1.370(5) . ?
C1 C6 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(3) . ?
C5 C10 1.468(3) . ?
C6 C7 1.500(4) . ?
C7 C8 1.516(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.502(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.341(3) . ?
C10 C11 1.512(3) . ?
C11 C14 1.530(3) . ?
C11 C12 1.531(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.506(3) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.383(3) . ?
C14 C19 1.389(3) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
C9 O1 C13 116.84(17) . . ?
O3 N1 O2 122.4(3) . . ?
O3 N1 C12 119.0(3) . . ?
O2 N1 C12 118.60(19) . . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 C10 122.64(19) . . ?
C6 C5 C10 119.1(2) . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 122.3(2) . . ?
C5 C6 C7 118.5(2) . . ?
C6 C7 C8 112.8(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 109.8(2) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 O1 125.67(19) . . ?
C10 C9 C8 122.5(2) . . ?
O1 C9 C8 111.80(19) . . ?
C9 C10 C5 119.50(19) . . ?
C9 C10 C11 120.80(19) . . ?
C5 C10 C11 119.68(16) . . ?
C10 C11 C14 113.90(17) . . ?
C10 C11 C12 108.66(16) . . ?
C14 C11 C12 109.66(17) . . ?
C10 C11 H11 108.2 . . ?
C14 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C13 C12 N1 109.38(19) . . ?
C13 C12 C11 111.30(18) . . ?
N1 C12 C11 109.79(19) . . ?
C13 C12 H12 108.8 . . ?
N1 C12 H12 108.8 . . ?
C11 C12 H12 108.8 . . ?
O1 C13 C12 112.2(2) . . ?
O1 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
O1 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C19 117.9(2) . . ?
C15 C14 C11 122.25(17) . . ?
C19 C14 C11 119.86(19) . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?

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 0.3(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C10 179.1(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 -177.5(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C10 C5 C6 C1 -178.5(2) . . . . ?
C4 C5 C6 C7 177.4(2) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
C1 C6 C7 C8 -149.1(2) . . . . ?
C5 C6 C7 C8 34.0(3) . . . . ?
C6 C7 C8 C9 -47.6(3) . . . . ?
C13 O1 C9 C10 -6.9(3) . . . . ?
C13 O1 C9 C8 175.2(2) . . . . ?
C7 C8 C9 C10 33.4(3) . . . . ?
C7 C8 C9 O1 -148.7(2) . . . . ?
O1 C9 C10 C5 -179.3(2) . . . . ?
C8 C9 C10 C5 -1.7(3) . . . . ?
O1 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 C11 176.8(2) . . . . ?
C4 C5 C10 C9 165.3(2) . . . . ?
C6 C5 C10 C9 -15.8(3) . . . . ?
C4 C5 C10 C11 -13.2(3) . . . . ?
C6 C5 C10 C11 165.70(19) . . . . ?
C9 C10 C11 C14 102.4(2) . . . . ?
C5 C10 C11 C14 -79.1(2) . . . . ?
C9 C10 C11 C12 -20.1(3) . . . . ?
C5 C10 C11 C12 158.33(18) . . . . ?
O3 N1 C12 C13 20.6(4) . . . . ?
O2 N1 C12 C13 -161.2(3) . . . . ?
O3 N1 C12 C11 143.0(3) . . . . ?
O2 N1 C12 C11 -38.7(3) . . . . ?
C10 C11 C12 C13 47.4(2) . . . . ?
C14 C11 C12 C13 -77.7(2) . . . . ?
C10 C11 C12 N1 -73.9(2) . . . . ?
C14 C11 C12 N1 161.04(16) . . . . ?
C9 O1 C13 C12 35.8(3) . . . . ?
N1 C12 C13 O1 64.4(3) . . . . ?
C11 C12 C13 O1 -57.1(3) . . . . ?
C10 C11 C14 C15 -20.7(3) . . . . ?
C12 C11 C14 C15 101.3(2) . . . . ?
C10 C11 C14 C19 159.2(2) . . . . ?
C12 C11 C14 C19 -78.8(2) . . . . ?
C19 C14 C15 C16 1.5(3) . . . . ?
C11 C14 C15 C16 -178.6(2) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C15 C14 C19 C18 -1.7(4) . . . . ?
C11 C14 C19 C18 178.4(2) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036

