# Supplementary Information (SI) for Chemical Communications.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2352397'
loop_
_audit_author_name
_audit_author_address
'Dr. Chandan K Jana'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-05-01 deposited with the CCDC.	2024-07-08 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            'C23 H18 N2 O3'
_chemical_formula_weight         370.39

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.840(10)
_cell_length_b                   11.120(16)
_cell_length_c                   24.67(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1876(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1596
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      21.19

_exptl_crystal_description       colorless
_exptl_crystal_colour            plate
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             776.0
_exptl_transmission_factor_min   0.977
_exptl_transmission_factor_max   0.985
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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            41325
_diffrn_reflns_av_unetI/netI     0.2646
_diffrn_reflns_av_R_equivalents  0.5508
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.009
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3297
_reflns_number_gt                1199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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          
;
 Refined as a 2-component inversion twin.
;
_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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   10(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3297
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2613
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2428
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_restrained_S_all      0.904
_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 0.4985(10) 0.2139(6) 0.1587(3) 0.0588(19) Uani 1 1 d . . . . .
O3 O 0.0182(14) 0.2100(7) 0.0385(3) 0.087(3) Uani 1 1 d . . . . .
O2 O 0.5355(12) 0.4394(7) 0.0883(3) 0.080(3) Uani 1 1 d . . . . .
N2 N 0.2552(13) 0.3473(7) 0.0590(3) 0.047(2) Uani 1 1 d . . . . .
N1 N 0.3095(15) 0.1730(8) 0.1767(3) 0.062(2) Uani 1 1 d . . . . .
C10 C 0.179(2) 0.2334(10) 0.0562(4) 0.060(3) Uani 1 1 d . . . . .
C11 C 0.2446(17) 0.0872(8) 0.1353(4) 0.060(3) Uani 1 1 d . . . . .
H11 H 0.101358 0.084920 0.134912 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1593(16) 0.4510(8) 0.0388(4) 0.046(3) Uani 1 1 d . . . . .
C23 C -0.014(2) 0.2508(11) 0.2001(4) 0.068(3) Uani 1 1 d . . . . .
H23 H -0.066578 0.174218 0.195889 0.082 Uiso 1 1 calc R U . . .
C12 C 0.321(2) -0.0379(9) 0.1434(4) 0.061(3) Uani 1 1 d . . . . .
C18 C 0.1817(18) 0.2722(9) 0.1895(3) 0.050(3) Uani 1 1 d . . . . .
C9 C 0.3196(17) 0.1453(9) 0.0809(4) 0.057(3) Uani 1 1 d . . . . .
H9 H 0.360606 0.084042 0.054715 0.068 Uiso 1 1 calc R U . . .
C7 C 0.4420(18) 0.3495(11) 0.0814(4) 0.054(3) Uani 1 1 d . . . . .
C13 C 0.213(2) -0.1333(11) 0.1254(4) 0.088(4) Uani 1 1 d . . . . .
H13 H 0.091507 -0.118985 0.109591 0.106 Uiso 1 1 calc R U . . .
C8 C 0.4897(17) 0.2225(9) 0.0990(4) 0.061(3) Uani 1 1 d . . . . .
H8 H 0.612226 0.194899 0.082620 0.073 Uiso 1 1 calc R U . . .
C6 C -0.0153(17) 0.4867(10) 0.0589(4) 0.063(3) Uani 1 1 d . . . . .
H6 H -0.072816 0.442358 0.086572 0.076 Uiso 1 1 calc R U . . .
C4 C 0.2402(18) 0.5133(9) -0.0046(4) 0.065(3) Uani 1 1 d . . . . .
H4 H 0.356643 0.487442 -0.020205 0.078 Uiso 1 1 calc R U . . .
C2 C -0.029(2) 0.6482(11) -0.0028(5) 0.077(3) Uani 1 1 d . . . . .
H2 H -0.095079 0.714451 -0.016875 0.092 Uiso 1 1 calc R U . . .
C14 C 0.278(3) -0.2504(12) 0.1301(6) 0.105(5) Uani 1 1 d . . . . .
H14 H 0.200872 -0.313759 0.118086 0.126 Uiso 1 1 calc R U . . .
C17 C 0.501(2) -0.0616(10) 0.1673(4) 0.080(4) Uani 1 1 d . . . . .
H17 H 0.577702 0.001107 0.180175 0.096 Uiso 1 1 calc R U . . .
C22 C -0.1275(19) 0.3435(14) 0.2167(5) 0.081(4) Uani 1 1 d . . . . .
H22 H -0.258401 0.327894 0.224132 0.098 Uiso 1 1 calc R U . . .
C1 C -0.1089(16) 0.5852(11) 0.0396(5) 0.069(3) Uani 1 1 d . . . . .
H1 H -0.226183 0.609982 0.055054 0.083 Uiso 1 1 calc R U . . .
C20 C 0.134(2) 0.4776(11) 0.2142(5) 0.076(4) Uani 1 1 d . . . . .
H20 H 0.185857 0.554264 0.219214 0.091 Uiso 1 1 calc R U . . .
C19 C 0.2560(17) 0.3863(10) 0.1982(4) 0.060(3) Uani 1 1 d . . . . .
H19 H 0.388607 0.401073 0.193098 0.072 Uiso 1 1 calc R U . . .
C3 C 0.1457(19) 0.6141(10) -0.0243(4) 0.068(3) Uani 1 1 d . . . . .
H3 H 0.201480 0.658665 -0.052218 0.081 Uiso 1 1 calc R U . . .
C15 C 0.455(3) -0.2723(13) 0.1520(5) 0.096(5) Uani 1 1 d . . . . .
H15 H 0.501619 -0.350697 0.153781 0.115 Uiso 1 1 calc R U . . .
C16 C 0.565(2) -0.1801(13) 0.1717(5) 0.093(4) Uani 1 1 d . . . . .
H16 H 0.684131 -0.196380 0.188304 0.111 Uiso 1 1 calc R U . . .
C21 C -0.061(2) 0.4588(12) 0.2232(5) 0.082(4) Uani 1 1 d . . . . .
H21 H -0.144646 0.521088 0.233142 0.098 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 N1 1.441(10) . ?
O1 C8 1.475(11) . ?
O3 C10 1.214(12) . ?
O2 C7 1.199(12) . ?
N2 C10 1.371(13) . ?
N2 C7 1.393(12) . ?
N2 C5 1.417(11) . ?
N1 C18 1.442(12) . ?
N1 C11 1.466(11) . ?
C10 C9 1.501(14) . ?
C11 C12 1.499(13) . ?
C11 C9 1.577(12) . ?
C5 C6 1.352(13) . ?
C5 C4 1.391(13) . ?
C23 C22 1.354(14) . ?
C23 C18 1.385(14) . ?
C12 C13 1.368(13) . ?
C12 C17 1.389(15) . ?
C18 C19 1.384(12) . ?
C9 C8 1.513(13) . ?
C7 C8 1.513(14) . ?
C13 C14 1.382(16) . ?
C6 C1 1.355(13) . ?
C4 C3 1.383(13) . ?
C2 C3 1.364(14) . ?
C2 C1 1.371(15) . ?
C14 C15 1.345(18) . ?
C17 C16 1.393(15) . ?
C22 C21 1.369(15) . ?
C20 C19 1.371(14) . ?
C20 C21 1.373(16) . ?
C15 C16 1.362(16) . ?

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 O1 C8 107.0(7) . . ?
C10 N2 C7 112.6(9) . . ?
C10 N2 C5 124.0(9) . . ?
C7 N2 C5 123.4(9) . . ?
O1 N1 C18 111.7(8) . . ?
O1 N1 C11 105.2(8) . . ?
C18 N1 C11 117.8(8) . . ?
O3 C10 N2 124.1(11) . . ?
O3 C10 C9 125.9(11) . . ?
N2 C10 C9 109.9(10) . . ?
N1 C11 C12 114.0(8) . . ?
N1 C11 C9 103.1(8) . . ?
C12 C11 C9 112.3(8) . . ?
C6 C5 C4 119.1(10) . . ?
C6 C5 N2 121.3(10) . . ?
C4 C5 N2 119.5(10) . . ?
C22 C23 C18 118.7(11) . . ?
C13 C12 C17 118.0(11) . . ?
C13 C12 C11 119.2(12) . . ?
C17 C12 C11 122.7(11) . . ?
C19 C18 C23 118.9(11) . . ?
C19 C18 N1 120.8(10) . . ?
C23 C18 N1 119.8(10) . . ?
C10 C9 C8 104.0(9) . . ?
C10 C9 C11 113.9(9) . . ?
C8 C9 C11 103.4(8) . . ?
O2 C7 N2 124.1(10) . . ?
O2 C7 C8 128.5(11) . . ?
N2 C7 C8 107.2(10) . . ?
C12 C13 C14 121.8(13) . . ?
O1 C8 C7 110.9(8) . . ?
O1 C8 C9 106.8(8) . . ?
C7 C8 C9 106.2(9) . . ?
C5 C6 C1 121.8(11) . . ?
C3 C4 C5 119.3(11) . . ?
C3 C2 C1 120.2(12) . . ?
C15 C14 C13 119.7(14) . . ?
C12 C17 C16 119.5(12) . . ?
C23 C22 C21 124.0(13) . . ?
C6 C1 C2 119.6(11) . . ?
C19 C20 C21 121.7(12) . . ?
C20 C19 C18 120.1(11) . . ?
C2 C3 C4 119.9(11) . . ?
C14 C15 C16 120.3(14) . . ?
C15 C16 C17 120.6(14) . . ?
C22 C21 C20 116.5(13) . . ?

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
C8 O1 N1 C18 -92.3(8) . . . . ?
C8 O1 N1 C11 36.6(9) . . . . ?
C7 N2 C10 O3 179.6(10) . . . . ?
C5 N2 C10 O3 -3.5(15) . . . . ?
C7 N2 C10 C9 2.6(11) . . . . ?
C5 N2 C10 C9 179.5(8) . . . . ?
O1 N1 C11 C12 84.4(10) . . . . ?
C18 N1 C11 C12 -150.4(9) . . . . ?
O1 N1 C11 C9 -37.6(9) . . . . ?
C18 N1 C11 C9 87.6(10) . . . . ?
C10 N2 C5 C6 61.7(13) . . . . ?
C7 N2 C5 C6 -121.7(10) . . . . ?
C10 N2 C5 C4 -114.4(11) . . . . ?
C7 N2 C5 C4 62.2(13) . . . . ?
N1 C11 C12 C13 150.8(10) . . . . ?
C9 C11 C12 C13 -92.4(12) . . . . ?
N1 C11 C12 C17 -30.8(15) . . . . ?
C9 C11 C12 C17 86.0(12) . . . . ?
C22 C23 C18 C19 2.4(15) . . . . ?
C22 C23 C18 N1 174.2(9) . . . . ?
O1 N1 C18 C19 -17.5(11) . . . . ?
C11 N1 C18 C19 -139.4(9) . . . . ?
O1 N1 C18 C23 170.9(8) . . . . ?
C11 N1 C18 C23 48.9(12) . . . . ?
O3 C10 C9 C8 -176.7(10) . . . . ?
N2 C10 C9 C8 0.3(10) . . . . ?
O3 C10 C9 C11 -64.9(13) . . . . ?
N2 C10 C9 C11 112.0(9) . . . . ?
N1 C11 C9 C10 -87.4(11) . . . . ?
C12 C11 C9 C10 149.5(10) . . . . ?
N1 C11 C9 C8 24.8(10) . . . . ?
C12 C11 C9 C8 -98.4(10) . . . . ?
C10 N2 C7 O2 -179.1(9) . . . . ?
C5 N2 C7 O2 4.0(15) . . . . ?
C10 N2 C7 C8 -4.3(10) . . . . ?
C5 N2 C7 C8 178.8(8) . . . . ?
C17 C12 C13 C14 -0.6(17) . . . . ?
C11 C12 C13 C14 177.9(11) . . . . ?
N1 O1 C8 C7 95.5(10) . . . . ?
N1 O1 C8 C9 -19.7(9) . . . . ?
O2 C7 C8 O1 63.1(14) . . . . ?
N2 C7 C8 O1 -111.4(9) . . . . ?
O2 C7 C8 C9 178.7(10) . . . . ?
N2 C7 C8 C9 4.2(10) . . . . ?
C10 C9 C8 O1 115.7(8) . . . . ?
C11 C9 C8 O1 -3.5(10) . . . . ?
C10 C9 C8 C7 -2.7(9) . . . . ?
C11 C9 C8 C7 -121.9(8) . . . . ?
C4 C5 C6 C1 -3.5(15) . . . . ?
N2 C5 C6 C1 -179.6(9) . . . . ?
C6 C5 C4 C3 3.6(15) . . . . ?
N2 C5 C4 C3 179.7(9) . . . . ?
C12 C13 C14 C15 -1(2) . . . . ?
C13 C12 C17 C16 0.5(16) . . . . ?
C11 C12 C17 C16 -177.9(10) . . . . ?
C18 C23 C22 C21 0.8(17) . . . . ?
C5 C6 C1 C2 2.7(16) . . . . ?
C3 C2 C1 C6 -2.0(17) . . . . ?
C21 C20 C19 C18 1.3(16) . . . . ?
C23 C18 C19 C20 -3.4(14) . . . . ?
N1 C18 C19 C20 -175.1(9) . . . . ?
C1 C2 C3 C4 2.2(16) . . . . ?
C5 C4 C3 C2 -3.0(15) . . . . ?
C13 C14 C15 C16 3(2) . . . . ?
C14 C15 C16 C17 -3(2) . . . . ?
C12 C17 C16 C15 1.2(17) . . . . ?
C23 C22 C21 C20 -2.9(18) . . . . ?
C19 C20 C21 C22 1.8(18) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.061



