# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_33
_database_code_depnum_ccdc_archive 'CCDC 2379596'
loop_
_audit_author_name
_audit_author_address
'Prabhakaran M'
;University of Madras
India
;
_audit_update_record             
;
2024-08-24 deposited with the CCDC.	2024-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N O3'
_chemical_formula_weight         318.34

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                   9.5665(4)
_cell_length_b                   9.9423(4)
_cell_length_c                   10.1434(6)
_cell_angle_alpha                119.1405(13)
_cell_angle_beta                 91.334(2)
_cell_angle_gamma                97.5234(17)
_cell_volume                     831.17(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5875
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.09

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             334
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10941
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2912
_reflns_number_gt                2459
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0726P)²+0.2461P] 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         2912
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.28459(17) 0.55250(19) 1.23024(18) 0.0406(4) Uani 1 1 d . . . . .
C2 C 0.2679(2) 0.6361(2) 1.3823(2) 0.0518(5) Uani 1 1 d . . . . .
H2 H 0.3043 0.6099 1.4510 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1951(2) 0.7603(2) 1.4292(2) 0.0597(5) Uani 1 1 d . . . . .
H3 H 0.1836 0.8200 1.5316 0.072 Uiso 1 1 calc R U . . .
C4 C 0.1391(2) 0.7973(2) 1.3267(2) 0.0598(5) Uani 1 1 d . . . . .
H4 H 0.0872 0.8789 1.3604 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1590(2) 0.7148(2) 1.1745(2) 0.0507(5) Uani 1 1 d . . . . .
H5 H 0.1217 0.7412 1.1063 0.061 Uiso 1 1 calc R U . . .
C6 C 0.23524(17) 0.59241(19) 1.12480(18) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.27680(16) 0.48221(18) 0.97696(18) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.34519(17) 0.36736(19) 1.00389(18) 0.0398(4) Uani 1 1 d . . . . .
C9 C 0.26827(16) 0.48344(18) 0.84326(18) 0.0364(4) Uani 1 1 d . . . . .
C10 C 0.21408(17) 0.61350(18) 0.83478(17) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.29745(19) 0.7595(2) 0.8960(2) 0.0463(4) Uani 1 1 d . . . . .
H11 H 0.3883 0.7763 0.9416 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2461(2) 0.8803(2) 0.8897(2) 0.0539(5) Uani 1 1 d . . . . .
H12 H 0.3032 0.9775 0.9314 0.065 Uiso 1 1 calc R U . . .
C13 C 0.1118(2) 0.8596(2) 0.8228(2) 0.0544(5) Uani 1 1 d . . . . .
C14 C 0.0303(2) 0.7135(3) 0.7607(2) 0.0616(5) Uani 1 1 d . . . . .
H14 H -0.0603 0.6968 0.7146 0.074 Uiso 1 1 calc R U . . .
C15 C 0.08049(19) 0.5910(2) 0.7654(2) 0.0519(5) Uani 1 1 d . . . . .
H15 H 0.0239 0.4933 0.7218 0.062 Uiso 1 1 calc R U . . .
C16 C 0.0556(3) 0.9927(3) 0.8182(3) 0.0849(8) Uani 1 1 d . . . . .
H16A H 0.0529 1.0754 0.9199 0.127 Uiso 1 1 calc R U . . .
H16B H -0.0383 0.9564 0.7664 0.127 Uiso 1 1 calc R U . . .
H16C H 0.1165 1.0307 0.7655 0.127 Uiso 1 1 calc R U . . .
C17 C 0.31516(17) 0.36308(19) 0.70629(18) 0.0401(4) Uani 1 1 d . . . . .
H17 H 0.3442 0.2790 0.7095 0.048 Uiso 1 1 calc R U . . .
C18 C 0.3190(2) 0.3659(2) 0.57704(19) 0.0487(4) Uani 1 1 d . . . . .
H18 H 0.2846 0.4472 0.5730 0.058 Uiso 1 1 calc R U . . .
C19 C 0.3732(2) 0.2509(2) 0.44015(19) 0.0490(4) Uani 1 1 d . . . . .
C20 C 0.4652(3) 0.0155(2) 0.3203(2) 0.0653(6) Uani 1 1 d . . . . .
H20A H 0.4045 -0.0201 0.2291 0.098 Uiso 1 1 calc R U . . .
H20B H 0.4750 -0.0714 0.3349 0.098 Uiso 1 1 calc R U . . .
H20C H 0.5567 0.0619 0.3120 0.098 Uiso 1 1 calc R U . . .
N1 N 0.34958(15) 0.41997(17) 1.15608(16) 0.0453(4) Uani 1 1 d . . . . .
O1 O 0.39101(15) 0.25132(15) 0.91377(14) 0.0571(4) Uani 1 1 d . . . . .
O2 O 0.3909(2) 0.2669(2) 0.33121(17) 0.0908(6) Uani 1 1 d . . . . .
O3 O 0.40424(15) 0.12996(14) 0.44820(13) 0.0547(4) 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 C2 1.376(2) . ?
C1 N1 1.400(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.466(2) . ?
C7 C9 1.363(2) . ?
C7 C8 1.516(2) . ?
C8 O1 1.218(2) . ?
C8 N1 1.365(2) . ?
C9 C17 1.454(2) . ?
C9 C10 1.493(2) . ?
C10 C15 1.381(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 C16 1.512(2) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.326(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.465(2) . ?
C18 H18 0.9300 . ?
C19 O2 1.204(2) . ?
C19 O3 1.315(2) . ?
C20 O3 1.446(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 C1 N1 127.84(15) . . ?
C2 C1 C6 122.52(16) . . ?
N1 C1 C6 109.64(14) . . ?
C1 C2 C3 117.64(17) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 121.03(17) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.96(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.24(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.47(15) . . ?
C5 C6 C7 134.35(15) . . ?
C1 C6 C7 107.15(13) . . ?
C9 C7 C6 129.49(14) . . ?
C9 C7 C8 125.02(14) . . ?
C6 C7 C8 105.32(12) . . ?
O1 C8 N1 124.21(14) . . ?
O1 C8 C7 129.55(15) . . ?
N1 C8 C7 106.23(13) . . ?
C7 C9 C17 121.96(14) . . ?
C7 C9 C10 120.32(14) . . ?
C17 C9 C10 117.69(13) . . ?
C15 C10 C11 118.63(15) . . ?
C15 C10 C9 120.85(15) . . ?
C11 C10 C9 120.52(14) . . ?
C12 C11 C10 120.33(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 121.45(18) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 117.78(16) . . ?
C14 C13 C16 121.1(2) . . ?
C12 C13 C16 121.2(2) . . ?
C13 C14 C15 121.48(18) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 120.32(18) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C9 124.01(15) . . ?
C18 C17 H17 118.0 . . ?
C9 C17 H17 118.0 . . ?
C17 C18 C19 125.09(15) . . ?
C17 C18 H18 117.5 . . ?
C19 C18 H18 117.5 . . ?
O2 C19 O3 122.79(17) . . ?
O2 C19 C18 123.22(16) . . ?
O3 C19 C18 113.97(14) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 C1 111.46(13) . . ?
C19 O3 C20 117.09(14) . . ?

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 -177.61(17) . . . . ?
C6 C1 C2 C3 2.3(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -2.6(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 2.6(3) . . . . ?
C4 C5 C6 C7 -179.91(18) . . . . ?
C2 C1 C6 C5 -4.1(3) . . . . ?
N1 C1 C6 C5 175.76(15) . . . . ?
C2 C1 C6 C7 177.72(16) . . . . ?
N1 C1 C6 C7 -2.37(19) . . . . ?
C5 C6 C7 C9 10.9(3) . . . . ?
C1 C6 C7 C9 -171.42(16) . . . . ?
C5 C6 C7 C8 -173.63(19) . . . . ?
C1 C6 C7 C8 4.06(17) . . . . ?
C9 C7 C8 O1 -7.6(3) . . . . ?
C6 C7 C8 O1 176.69(18) . . . . ?
C9 C7 C8 N1 171.37(15) . . . . ?
C6 C7 C8 N1 -4.38(17) . . . . ?
C6 C7 C9 C17 179.99(15) . . . . ?
C8 C7 C9 C17 5.3(3) . . . . ?
C6 C7 C9 C10 2.0(3) . . . . ?
C8 C7 C9 C10 -172.63(14) . . . . ?
C7 C9 C10 C15 -105.91(19) . . . . ?
C17 C9 C10 C15 76.1(2) . . . . ?
C7 C9 C10 C11 74.4(2) . . . . ?
C17 C9 C10 C11 -103.67(18) . . . . ?
C15 C10 C11 C12 1.1(2) . . . . ?
C9 C10 C11 C12 -179.15(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C11 C12 C13 C16 179.10(17) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C16 C13 C14 C15 -179.42(18) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
C9 C10 C15 C14 178.84(16) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C7 C9 C17 C18 -174.62(17) . . . . ?
C10 C9 C17 C18 3.4(2) . . . . ?
C9 C17 C18 C19 176.37(17) . . . . ?
C17 C18 C19 O2 -170.7(2) . . . . ?
C17 C18 C19 O3 7.6(3) . . . . ?
O1 C8 N1 C1 -177.88(16) . . . . ?
C7 C8 N1 C1 3.11(18) . . . . ?
C2 C1 N1 C8 179.36(17) . . . . ?
C6 C1 N1 C8 -0.5(2) . . . . ?
O2 C19 O3 C20 1.5(3) . . . . ?
C18 C19 O3 C20 -176.87(17) . . . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049

