# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_GC_IND_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2382458'
loop_
_audit_author_name
_audit_author_address
'Gopal Chakrabortty'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2024-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.71 H2.12 N0.24 O0.12'
_chemical_formula_weight         39.81

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.0903(8)
_cell_length_b                   10.8057(6)
_cell_length_c                   11.6002(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.060(2)
_cell_angle_gamma                90
_cell_volume                     1720.51(16)
_cell_formula_units_Z            34
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6187
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      23.59

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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            42311
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         24.840
_diffrn_reflns_theta_full        24.840
_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             2964
_reflns_number_gt                2434
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0430P)²+0.6364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_1 O 0.80913(9) 0.52741(11) 0.11174(10) 0.0483(3) Uani 1 1 d . . . . .
N1_1 N 0.48041(10) 0.52828(13) 0.16331(12) 0.0433(4) Uani 1 1 d . . . . .
N2_1 N 0.76959(11) 0.68827(13) 0.36144(12) 0.0406(4) Uani 1 1 d . . . . .
H1_1 H 0.7311(15) 0.7146(19) 0.3978(18) 0.061 Uiso 1 1 d . U . . .
C1_1 C 0.77714(11) 0.45835(15) 0.35409(14) 0.0375(4) Uani 1 1 d . . . . .
C2_1 C 0.76588(13) 0.34572(16) 0.29549(16) 0.0462(4) Uani 1 1 d . . . . .
H2_1 H 0.735757 0.343082 0.215456 0.055 Uiso 1 1 calc R U . . .
C3_1 C 0.79866(14) 0.23751(17) 0.35408(19) 0.0562(5) Uani 1 1 d . . . . .
H3_1 H 0.790584 0.162727 0.313351 0.067 Uiso 1 1 calc R U . . .
C4_1 C 0.84321(15) 0.2396(2) 0.4723(2) 0.0656(6) Uani 1 1 d . . . . .
H4_1 H 0.864935 0.166546 0.511941 0.079 Uiso 1 1 calc R U . . .
C5_1 C 0.85530(17) 0.3497(2) 0.5311(2) 0.0731(7) Uani 1 1 d . . . . .
H5_1 H 0.885870 0.351487 0.611034 0.088 Uiso 1 1 calc R U . . .
C6_1 C 0.82255(15) 0.45927(19) 0.47317(16) 0.0560(5) Uani 1 1 d . . . . .
H6_1 H 0.831131 0.533679 0.514503 0.067 Uiso 1 1 calc R U . . .
C7_1 C 0.74435(11) 0.57843(14) 0.28610(13) 0.0347(4) Uani 1 1 d . . . . .
C8_1 C 0.63862(11) 0.57841(14) 0.22316(13) 0.0352(4) Uani 1 1 d . . . . .
C9_1 C 0.56826(12) 0.49559(15) 0.23420(14) 0.0397(4) Uani 1 1 d . . . . .
H9_1 H 0.578532 0.426419 0.283139 0.048 Uiso 1 1 calc R U . . .
C10_1 C 0.39007(14) 0.4597(2) 0.15000(19) 0.0594(5) Uani 1 1 d . . . . .
H10A_1 H 0.356395 0.459248 0.068219 0.089 Uiso 1 1 calc R U . . .
H10B_1 H 0.349858 0.498194 0.196376 0.089 Uiso 1 1 calc R U . . .
H10C_1 H 0.404172 0.376129 0.176583 0.089 Uiso 1 1 calc R U . . .
C11_1 C 0.49300(12) 0.63474(16) 0.10363(14) 0.0414(4) Uani 1 1 d . . . . .
C12_1 C 0.42564(14) 0.70132(19) 0.02033(16) 0.0544(5) Uani 1 1 d . . . . .
H12_1 H 0.360861 0.676666 -0.002528 0.065 Uiso 1 1 calc R U . . .
C13_1 C 0.45883(17) 0.8048(2) -0.02659(18) 0.0633(6) Uani 1 1 d . . . . .
H13_1 H 0.415556 0.850960 -0.082680 0.076 Uiso 1 1 calc R U . . .
C14_1 C 0.55581(16) 0.84259(18) 0.00756(17) 0.0581(5) Uani 1 1 d . . . . .
H14_1 H 0.575707 0.913402 -0.025983 0.070 Uiso 1 1 calc R U . . .
C15_1 C 0.62262(14) 0.77699(16) 0.09005(15) 0.0460(4) Uani 1 1 d . . . . .
H15_1 H 0.686996 0.803286 0.112758 0.055 Uiso 1 1 calc R U . . .
C16_1 C 0.59169(12) 0.66954(15) 0.13929(13) 0.0372(4) Uani 1 1 d . . . . .
C17_1 C 0.81056(11) 0.59595(14) 0.19549(13) 0.0350(4) Uani 1 1 d . . . . .
C18_1 C 0.86833(11) 0.70624(14) 0.23059(14) 0.0355(4) Uani 1 1 d . . . . .
C19_1 C 0.83788(11) 0.76017(14) 0.32549(13) 0.0355(4) Uani 1 1 d . . . . .
C20_1 C 0.87566(13) 0.87379(15) 0.37081(15) 0.0446(4) Uani 1 1 d . . . . .
H20_1 H 0.854831 0.911647 0.432740 0.054 Uiso 1 1 calc R U . . .
C21_1 C 0.94493(13) 0.92790(17) 0.32049(17) 0.0519(5) Uani 1 1 d . . . . .
H21_1 H 0.971823 1.003080 0.350453 0.062 Uiso 1 1 calc R U . . .
C22_1 C 0.97639(13) 0.87423(18) 0.22616(17) 0.0512(5) Uani 1 1 d . . . . .
H22_1 H 1.023468 0.913626 0.194612 0.061 Uiso 1 1 calc R U . . .
C23_1 C 0.93811(12) 0.76390(16) 0.18011(15) 0.0431(4) Uani 1 1 d . . . . .
H23_1 H 0.957993 0.727934 0.116641 0.052 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_1 C17_1 1.2181(18) . ?
N1_1 C9_1 1.369(2) . ?
N1_1 C11_1 1.375(2) . ?
N1_1 C10_1 1.451(2) . ?
N2_1 C19_1 1.373(2) . ?
N2_1 C7_1 1.469(2) . ?
C1_1 C6_1 1.385(2) . ?
C1_1 C2_1 1.385(2) . ?
C1_1 C7_1 1.534(2) . ?
C2_1 C3_1 1.379(2) . ?
C3_1 C4_1 1.374(3) . ?
C4_1 C5_1 1.363(3) . ?
C5_1 C6_1 1.388(3) . ?
C7_1 C8_1 1.504(2) . ?
C7_1 C17_1 1.567(2) . ?
C8_1 C9_1 1.363(2) . ?
C8_1 C16_1 1.436(2) . ?
C11_1 C12_1 1.392(2) . ?
C11_1 C16_1 1.409(2) . ?
C12_1 C13_1 1.371(3) . ?
C13_1 C14_1 1.395(3) . ?
C14_1 C15_1 1.377(3) . ?
C15_1 C16_1 1.406(2) . ?
C17_1 C18_1 1.449(2) . ?
C18_1 C19_1 1.396(2) . ?
C18_1 C23_1 1.399(2) . ?
C19_1 C20_1 1.393(2) . ?
C20_1 C21_1 1.376(3) . ?
C21_1 C22_1 1.396(3) . ?
C22_1 C23_1 1.366(2) . ?

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_1 N1_1 C11_1 108.45(14) . . ?
C9_1 N1_1 C10_1 125.78(15) . . ?
C11_1 N1_1 C10_1 125.74(15) . . ?
C19_1 N2_1 C7_1 111.62(13) . . ?
C6_1 C1_1 C2_1 118.13(16) . . ?
C6_1 C1_1 C7_1 121.61(15) . . ?
C2_1 C1_1 C7_1 120.19(14) . . ?
C3_1 C2_1 C1_1 120.98(17) . . ?
C4_1 C3_1 C2_1 120.31(19) . . ?
C5_1 C4_1 C3_1 119.44(18) . . ?
C4_1 C5_1 C6_1 120.8(2) . . ?
C1_1 C6_1 C5_1 120.3(2) . . ?
N2_1 C7_1 C8_1 111.66(13) . . ?
N2_1 C7_1 C1_1 111.91(12) . . ?
C8_1 C7_1 C1_1 113.56(13) . . ?
N2_1 C7_1 C17_1 101.58(12) . . ?
C8_1 C7_1 C17_1 110.43(12) . . ?
C1_1 C7_1 C17_1 106.93(12) . . ?
C9_1 C8_1 C16_1 106.29(14) . . ?
C9_1 C8_1 C7_1 128.05(14) . . ?
C16_1 C8_1 C7_1 125.65(14) . . ?
C8_1 C9_1 N1_1 110.64(14) . . ?
N1_1 C11_1 C12_1 129.55(17) . . ?
N1_1 C11_1 C16_1 107.85(14) . . ?
C12_1 C11_1 C16_1 122.59(17) . . ?
C13_1 C12_1 C11_1 117.17(19) . . ?
C12_1 C13_1 C14_1 121.75(18) . . ?
C15_1 C14_1 C13_1 121.22(18) . . ?
C14_1 C15_1 C16_1 118.77(18) . . ?
C15_1 C16_1 C11_1 118.49(15) . . ?
C15_1 C16_1 C8_1 134.74(16) . . ?
C11_1 C16_1 C8_1 106.77(14) . . ?
O1_1 C17_1 C18_1 129.15(15) . . ?
O1_1 C17_1 C7_1 123.82(14) . . ?
C18_1 C17_1 C7_1 107.02(13) . . ?
C19_1 C18_1 C23_1 120.95(15) . . ?
C19_1 C18_1 C17_1 108.16(13) . . ?
C23_1 C18_1 C17_1 130.69(15) . . ?
N2_1 C19_1 C20_1 128.20(15) . . ?
N2_1 C19_1 C18_1 111.39(14) . . ?
C20_1 C19_1 C18_1 120.41(15) . . ?
C21_1 C20_1 C19_1 117.49(16) . . ?
C20_1 C21_1 C22_1 122.50(17) . . ?
C23_1 C22_1 C21_1 120.10(17) . . ?
C22_1 C23_1 C18_1 118.53(16) . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.032



