# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_rgss1
_database_code_depnum_ccdc_archive 'CCDC 2324472'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Shiv Nadar University
India
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2025-02-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         298.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.4417(6)
_cell_length_b                   7.7336(2)
_cell_length_c                   11.8813(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.5490(10)
_cell_angle_gamma                90
_cell_volume                     1543.98(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6394
_cell_measurement_theta_min      2.4242
_cell_measurement_theta_max      26.8621
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)


_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Venture'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            25609
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         26.93
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3337
_reflns_number_gt                2154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1812
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_number_reflns         3337
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+0.9336P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.34336(13) 0.1635(3) 0.7152(2) 0.0432(6) Uani d . . . 1 . .
C C2 0.36374(15) 0.1656(3) 0.6096(2) 0.0512(6) Uani d . . . 1 . .
H H2 0.328970 0.213362 0.543501 0.061000 Uiso calc U . R 1 . .
C C3 0.43552(17) 0.0969(4) 0.6027(3) 0.0642(8) Uani d . . . 1 . .
H H3 0.448553 0.099555 0.531810 0.077000 Uiso calc U . R 1 . .
C C4 0.48761(17) 0.0253(4) 0.6979(4) 0.0747(10) Uani d . . . 1 . .
H H4 0.535859 -0.019736 0.692203 0.090000 Uiso calc U . R 1 . .
C C5 0.46782(18) 0.0206(4) 0.8029(3) 0.0746(10) Uani d . . . 1 . .
H H5 0.502693 -0.029377 0.868008 0.089000 Uiso calc U . R 1 . .
C C6 0.39698(16) 0.0890(4) 0.8120(3) 0.0575(7) Uani d . . . 1 . .
H H6 0.384613 0.085798 0.883425 0.069000 Uiso calc U . R 1 . .
C C7 0.23584(13) 0.4546(3) 0.57671(19) 0.0382(5) Uani d . . . 1 . .
C C8 0.20570(14) 0.4868(3) 0.4583(2) 0.0420(5) Uani d . . . 1 . .
H H8 0.167238 0.413824 0.412978 0.050000 Uiso calc U . R 1 . .
C C9 0.23258(17) 0.6270(3) 0.4073(2) 0.0525(7) Uani d . . . 1 . .
H H9 0.212674 0.646913 0.327607 0.063000 Uiso calc U . R 1 . .
C C10 0.28866(18) 0.7373(4) 0.4741(3) 0.0611(7) Uani d . . . 1 . .
H H10 0.306931 0.830966 0.439537 0.073000 Uiso calc U . R 1 . .
C C11 0.31745(18) 0.7080(4) 0.5919(3) 0.0617(8) Uani d . . . 1 . .
H H11 0.355026 0.782796 0.637239 0.074000 Uiso calc U . R 1 . .
C C12 0.29111(15) 0.5690(3) 0.6433(2) 0.0503(6) Uani d . . . 1 . .
H H12 0.310481 0.551409 0.723309 0.060000 Uiso calc U . R 1 . .
C C13 0.20931(13) 0.3020(3) 0.63982(18) 0.0378(5) Uani d . . . 1 . .
C C14 0.14921(14) 0.3792(3) 0.70101(19) 0.0410(5) Uani d . . . 1 . .
C C15 0.02145(18) 0.5003(5) 0.6709(3) 0.0729(9) Uani d . . . 1 . .
H H15A 0.007343 0.420317 0.723766 0.109000 Uiso calc U . R 1 . .
H H15B -0.024710 0.526083 0.608124 0.109000 Uiso calc U . R 1 . .
H H15C 0.041404 0.604965 0.711796 0.109000 Uiso calc U . R 1 . .
C C16 0.12536(14) 0.0449(3) 0.5920(2) 0.0444(6) Uani d . . . 1 . .
C C17 0.09794(18) -0.1029(4) 0.5106(3) 0.0580(7) Uani d . . . 1 . .
H H17A 0.126154 -0.205699 0.543075 0.087000 Uiso calc U . R 1 . .
H H17B 0.108128 -0.077955 0.436756 0.087000 Uiso calc U . R 1 . .
H H17C 0.041901 -0.120132 0.499480 0.087000 Uiso calc U . R 1 . .
N N1 0.27433(12) 0.2362(3) 0.73181(18) 0.0456(5) Uani d . . . 1 . .
H H1N 0.2625(18) 0.208(4) 0.792(3) 0.068000 Uiso d U . . 1 . .
N N2 0.16954(12) 0.1685(3) 0.55795(17) 0.0419(5) Uani d . . . 1 . .
H H2N 0.1782(17) 0.157(4) 0.491(3) 0.063000 Uiso d U . . 1 . .
O O1 0.16419(11) 0.4056(2) 0.80442(14) 0.0533(5) Uani d . . . 1 . .
O O2 0.08220(10) 0.4245(3) 0.62396(14) 0.0521(5) Uani d . . . 1 . .
O O3 0.10974(11) 0.0553(3) 0.68647(15) 0.0578(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.390(3) ?
C1 C2 . 1.393(4) ?
C1 C6 . 1.398(4) ?
C2 C3 . 1.382(4) ?
C3 C4 . 1.364(5) ?
C4 C5 . 1.381(5) ?
C5 C6 . 1.375(4) ?
C7 C8 . 1.385(3) ?
C7 C12 . 1.389(3) ?
C7 C13 . 1.535(3) ?
C8 C9 . 1.384(3) ?
C9 C10 . 1.377(4) ?
C10 C11 . 1.373(4) ?
C11 C12 . 1.375(4) ?
C13 N1 . 1.441(3) ?
C13 N2 . 1.460(3) ?
C13 C14 . 1.547(3) ?
C14 O1 . 1.203(3) ?
C14 O2 . 1.324(3) ?
C15 O2 . 1.447(3) ?
C16 O3 . 1.226(3) ?
C16 N2 . 1.356(3) ?
C16 C17 . 1.491(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 124.3(2) ?
N1 C1 C6 . . 117.6(2) ?
C2 C1 C6 . . 118.1(2) ?
C3 C2 C1 . . 120.1(3) ?
C4 C3 C2 . . 121.3(3) ?
C3 C4 C5 . . 119.2(3) ?
C6 C5 C4 . . 120.5(3) ?
C5 C6 C1 . . 120.7(3) ?
C8 C7 C12 . . 118.7(2) ?
C8 C7 C13 . . 123.5(2) ?
C12 C7 C13 . . 117.8(2) ?
C9 C8 C7 . . 120.3(2) ?
C10 C9 C8 . . 120.3(2) ?
C11 C10 C9 . . 119.6(3) ?
C10 C11 C12 . . 120.5(3) ?
C11 C12 C7 . . 120.6(2) ?
N1 C13 N2 . . 113.11(19) ?
N1 C13 C7 . . 111.29(19) ?
N2 C13 C7 . . 111.71(18) ?
N1 C13 C14 . . 105.94(17) ?
N2 C13 C14 . . 108.99(18) ?
C7 C13 C14 . . 105.30(18) ?
O1 C14 O2 . . 124.8(2) ?
O1 C14 C13 . . 123.8(2) ?
O2 C14 C13 . . 111.15(18) ?
O3 C16 N2 . . 120.7(2) ?
O3 C16 C17 . . 122.2(2) ?
N2 C16 C17 . . 117.1(2) ?
C1 N1 C13 . . 124.8(2) ?
C16 N2 C13 . . 120.41(19) ?
C14 O2 C15 . . 116.28(19) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
