# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_PGN_12_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2216288'
loop_
_audit_author_name
_audit_author_address
'Swadhapriya Bhukta'
;The Cambridge Crystallographic Data Center 
India
;
_audit_update_record             
;
2022-10-29 deposited with the CCDC.	2023-05-17 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         'C33 H35 N3 O2'
_chemical_formula_sum            'C33 H35 N3 O2'
_chemical_formula_weight         505.64

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                   5.650(3)
_cell_length_b                   12.577(6)
_cell_length_c                   20.32(1)
_cell_angle_alpha                87.21(1)
_cell_angle_beta                 83.78(1)
_cell_angle_gamma                89.06(1)
_cell_volume                     1434.2(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2562
_cell_measurement_theta_min      0.981
_cell_measurement_theta_max      0.984

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             540.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_T_max  0.7455
_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      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26592
_diffrn_reflns_av_unetI/netI     0.1036
_diffrn_reflns_av_R_equivalents  0.1083
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         27.671
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6605
_reflns_number_gt                2562
_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    '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)+(0.1000P)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_number_reflns         6605
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2169
_refine_ls_R_factor_gt           0.0929
_refine_ls_wR_factor_ref         0.2753
_refine_ls_wR_factor_gt          0.2202
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_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 -0.1821(3) 0.18102(15) 0.54640(10) 0.0728(6) Uani 1 1 d . . . . .
O2 O 0.1611(4) 0.30843(16) 0.56434(11) 0.0801(7) Uani 1 1 d . . . . .
N1 N 0.6332(6) 0.6460(2) 0.18899(16) 0.0916(9) Uani 1 1 d . . . . .
C13 C 0.0779(5) 0.3197(2) 0.50330(16) 0.0626(8) Uani 1 1 d . . . . .
C1 C -0.4282(5) 0.0376(2) 0.59473(16) 0.0679(9) Uani 1 1 d . . . . .
N3 N 0.8563(5) 0.7846(2) 0.13566(14) 0.0913(9) Uani 1 1 d . . . . .
C2 C -0.6437(6) 0.0465(3) 0.63309(17) 0.0780(10) Uani 1 1 d . . . . .
H2 H -0.746312 0.102755 0.624381 0.094 Uiso 1 1 calc R U . . .
C8 C -0.1064(5) 0.2499(2) 0.49386(17) 0.0636(8) Uani 1 1 d . . . . .
C3 C -0.7095(7) -0.0270(3) 0.68422(19) 0.0905(11) Uani 1 1 d . . . . .
H3 H -0.856366 -0.020744 0.709327 0.109 Uiso 1 1 calc R U . . .
C4 C -0.5570(8) -0.1092(3) 0.6978(2) 0.0948(12) Uani 1 1 d . . . . .
H4 H -0.600000 -0.159123 0.732090 0.114 Uiso 1 1 calc R U . . .
N2 N 0.5833(8) 0.5830(3) 0.24638(16) 0.1117(12) Uani 1 1 d . . . . .
C11 C 0.0670(7) 0.3978(2) 0.39223(18) 0.0784(10) Uani 1 1 d . . . . .
C9 C -0.1992(6) 0.2569(3) 0.43361(18) 0.0758(9) Uani 1 1 d . . . . .
H9 H -0.322800 0.212377 0.426523 0.091 Uiso 1 1 calc R U . . .
C10 C -0.1114(6) 0.3293(3) 0.38342(17) 0.0827(10) Uani 1 1 d . . . . .
H10 H -0.175066 0.331270 0.343059 0.099 Uiso 1 1 calc R U . . .
C12 C 0.1614(6) 0.3903(2) 0.45271(18) 0.0761(10) Uani 1 1 d . . . . .
H12 H 0.285869 0.434802 0.459160 0.091 Uiso 1 1 calc R U . . .
C7 C -0.3711(6) 0.1108(3) 0.53511(17) 0.0805(10) Uani 1 1 d . . . . .
H7A H -0.322521 0.069579 0.496750 0.097 Uiso 1 1 calc R U . . .
H7B H -0.511482 0.152291 0.526363 0.097 Uiso 1 1 calc R U . . .
C14 C 0.3519(6) 0.3765(3) 0.57588(17) 0.0861(11) Uani 1 1 d . . . . .
H14A H 0.483758 0.366746 0.542694 0.129 Uiso 1 1 calc R U . . .
H14B H 0.400921 0.359015 0.618894 0.129 Uiso 1 1 calc R U . . .
H14C H 0.298667 0.449353 0.573783 0.129 Uiso 1 1 calc R U . . .
C20 C 0.8123(7) 0.7240(3) 0.18938(19) 0.0842(10) Uani 1 1 d . . . . .
C6 C -0.2787(6) -0.0448(3) 0.6099(2) 0.0886(11) Uani 1 1 d . . . . .
H6 H -0.131318 -0.051308 0.585114 0.106 Uiso 1 1 calc R U . . .
C19 C 0.4913(7) 0.6220(3) 0.1403(2) 0.0913(11) Uani 1 1 d . . . . .
C23 C 1.0328(7) 0.8583(3) 0.1359(2) 0.0908(11) Uani 1 1 d . . . . .
C5 C -0.3410(8) -0.1174(3) 0.6605(2) 0.1012(13) Uani 1 1 d . . . . .
H5 H -0.236596 -0.172746 0.669715 0.121 Uiso 1 1 calc R U . . .
C28 C 0.5018(7) 0.6754(3) 0.07216(18) 0.0933(11) Uani 1 1 d . . . . .
H28A H 0.658651 0.663809 0.048960 0.112 Uiso 1 1 calc R U . . .
H28B H 0.478916 0.751489 0.076304 0.112 Uiso 1 1 calc R U . . .
C21 C 0.9302(9) 0.7295(3) 0.2469(2) 0.1037(13) Uani 1 1 d . . . . .
H21 H 0.889365 0.684880 0.284054 0.124 Uiso 1 1 calc R U . . .
C22 C 1.1019(10) 0.8009(4) 0.2459(2) 0.1122(14) Uani 1 1 d . . . . .
H22 H 1.183232 0.806182 0.282946 0.135 Uiso 1 1 calc R U . . .
C33 C 1.1621(8) 0.8685(3) 0.1898(2) 0.0986(12) Uani 1 1 d . . . . .
C29 C 0.3156(7) 0.6345(3) 0.0315(2) 0.1040(13) Uani 1 1 d . . . . .
H29A H 0.158564 0.646351 0.054483 0.125 Uiso 1 1 calc R U . . .
H29B H 0.338105 0.558405 0.027301 0.125 Uiso 1 1 calc R U . . .
C18 C 0.3493(8) 0.5421(3) 0.1685(2) 0.1078(14) Uani 1 1 d . . . . .
H18 H 0.231391 0.508735 0.148708 0.129 Uiso 1 1 calc R U . . .
C30 C 0.3287(8) 0.6891(4) -0.0376(2) 0.1148(14) Uani 1 1 d . . . . .
H30A H 0.307750 0.765203 -0.033342 0.138 Uiso 1 1 calc R U . . .
H30B H 0.485436 0.676722 -0.060650 0.138 Uiso 1 1 calc R U . . .
C17 C 0.4125(10) 0.5189(3) 0.2327(3) 0.1204(17) Uani 1 1 d . . . . .
C15 C 0.1607(8) 0.4777(3) 0.3371(2) 0.1103(14) Uani 1 1 d . . . . .
H15A H 0.025331 0.510139 0.317948 0.132 Uiso 1 1 calc R U . . .
H15B H 0.241106 0.533740 0.356834 0.132 Uiso 1 1 calc R U . . .
C24 C 1.0818(8) 0.9259(4) 0.0788(2) 0.1249(16) Uani 1 1 d . . . . .
H24 H 0.995235 0.919874 0.042818 0.150 Uiso 1 1 calc R U . . .
C27 C 1.3443(10) 0.9446(4) 0.1847(3) 0.1348(17) Uani 1 1 d . . . . .
H27 H 1.435799 0.950414 0.219699 0.162 Uiso 1 1 calc R U . . .
C26 C 1.3885(10) 1.0098(4) 0.1293(3) 0.153(2) Uani 1 1 d . . . . .
H26 H 1.507510 1.060470 0.127079 0.183 Uiso 1 1 calc R U . . .
C16 C 0.3154(11) 0.4382(3) 0.2863(2) 0.158(2) Uani 1 1 d . . . . .
H16A H 0.233593 0.383692 0.265594 0.190 Uiso 1 1 calc R U . . .
H16B H 0.448802 0.404127 0.305441 0.190 Uiso 1 1 calc R U . . .
C31 C 0.1414(9) 0.6493(4) -0.0787(2) 0.1459(18) Uani 1 1 d . . . . .
H31A H 0.166047 0.573589 -0.083974 0.175 Uiso 1 1 calc R U . . .
H31B H -0.014702 0.659220 -0.054646 0.175 Uiso 1 1 calc R U . . .
C25 C 1.2572(10) 1.0008(4) 0.0764(3) 0.150(2) Uani 1 1 d . . . . .
H25 H 1.287683 1.045758 0.038848 0.180 Uiso 1 1 calc R U . . .
C32 C 0.1449(12) 0.7051(5) -0.1468(3) 0.189(3) Uani 1 1 d . . . . .
H32A H 0.081818 0.775999 -0.142386 0.284 Uiso 1 1 calc R U . . .
H32B H 0.049315 0.666239 -0.173492 0.284 Uiso 1 1 calc R U . . .
H32C H 0.305644 0.708127 -0.167610 0.284 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 C8 1.377(3) . ?
O1 C7 1.441(3) . ?
O2 C13 1.374(4) . ?
O2 C14 1.433(4) . ?
N1 N2 1.384(4) . ?
N1 C19 1.386(5) . ?
N1 C20 1.422(5) . ?
C13 C12 1.374(4) . ?
C13 C8 1.408(4) . ?
C1 C6 1.372(4) . ?
C1 C2 1.379(4) . ?
C1 C7 1.495(4) . ?
N3 C20 1.304(4) . ?
N3 C23 1.373(5) . ?
C2 C3 1.381(5) . ?
C8 C9 1.382(4) . ?
C3 C4 1.372(5) . ?
C4 C5 1.371(5) . ?
N2 C17 1.328(6) . ?
C11 C10 1.368(5) . ?
C11 C12 1.391(5) . ?
C11 C15 1.525(4) . ?
C9 C10 1.390(4) . ?
C20 C21 1.411(5) . ?
C6 C5 1.362(5) . ?
C19 C18 1.360(5) . ?
C19 C28 1.506(5) . ?
C23 C33 1.393(5) . ?
C23 C24 1.410(5) . ?
C28 C29 1.518(5) . ?
C21 C22 1.331(6) . ?
C22 C33 1.402(5) . ?
C33 C27 1.409(6) . ?
C29 C30 1.527(5) . ?
C18 C17 1.407(6) . ?
C30 C31 1.522(6) . ?
C17 C16 1.515(5) . ?
C15 C16 1.385(5) . ?
C24 C25 1.373(6) . ?
C27 C26 1.364(6) . ?
C26 C25 1.381(7) . ?
C31 C32 1.520(6) . ?

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
C8 O1 C7 115.3(2) . . ?
C13 O2 C14 116.8(2) . . ?
N2 N1 C19 112.3(3) . . ?
N2 N1 C20 116.8(4) . . ?
C19 N1 C20 130.9(3) . . ?
C12 C13 O2 125.8(3) . . ?
C12 C13 C8 119.5(3) . . ?
O2 C13 C8 114.7(3) . . ?
C6 C1 C2 118.0(3) . . ?
C6 C1 C7 121.6(3) . . ?
C2 C1 C7 120.2(3) . . ?
C20 N3 C23 116.5(3) . . ?
C1 C2 C3 121.0(3) . . ?
O1 C8 C9 125.4(3) . . ?
O1 C8 C13 116.8(3) . . ?
C9 C8 C13 117.9(3) . . ?
C4 C3 C2 119.6(3) . . ?
C5 C4 C3 119.6(4) . . ?
C17 N2 N1 104.4(4) . . ?
C10 C11 C12 117.5(3) . . ?
C10 C11 C15 120.9(4) . . ?
C12 C11 C15 121.6(4) . . ?
C8 C9 C10 121.3(3) . . ?
C11 C10 C9 121.3(3) . . ?
C13 C12 C11 122.6(3) . . ?
O1 C7 C1 109.7(3) . . ?
N3 C20 C21 125.1(4) . . ?
N3 C20 N1 116.8(4) . . ?
C21 C20 N1 118.2(4) . . ?
C5 C6 C1 121.5(3) . . ?
C18 C19 N1 104.6(4) . . ?
C18 C19 C28 129.9(4) . . ?
N1 C19 C28 125.5(3) . . ?
N3 C23 C33 122.7(4) . . ?
N3 C23 C24 117.7(4) . . ?
C33 C23 C24 119.6(4) . . ?
C6 C5 C4 120.2(4) . . ?
C19 C28 C29 112.8(3) . . ?
C22 C21 C20 117.5(4) . . ?
C21 C22 C33 121.1(4) . . ?
C23 C33 C22 117.2(4) . . ?
C23 C33 C27 118.6(4) . . ?
C22 C33 C27 124.3(5) . . ?
C28 C29 C30 112.3(3) . . ?
C19 C18 C17 107.9(4) . . ?
C31 C30 C29 112.8(4) . . ?
N2 C17 C18 110.8(4) . . ?
N2 C17 C16 118.0(5) . . ?
C18 C17 C16 131.2(6) . . ?
C16 C15 C11 116.5(3) . . ?
C25 C24 C23 120.0(4) . . ?
C26 C27 C33 121.1(5) . . ?
C27 C26 C25 120.2(5) . . ?
C15 C16 C17 116.0(4) . . ?
C32 C31 C30 113.9(4) . . ?
C24 C25 C26 120.5(5) . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.035

