# Supplementary Information (SI) for ChemComm.
# 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_TP_KV_1_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2372696'
loop_
_audit_author_name
_audit_author_address
'kshitiz verma'
;IIT guwahati
India
;
_audit_update_record             
;
2024-07-22 deposited with the CCDC.	2024-10-21 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         'C27 H25 N O5'
_chemical_formula_sum            'C27 H25 N O5'
_chemical_formula_weight         443.48

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   18.656(4)
_cell_length_b                   9.9609(18)
_cell_length_c                   12.339(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2293.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9843
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.089
_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      299(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            56725
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.183
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5248
_reflns_number_gt                3994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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)+(0.0281P)²+0.7900P] 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 
;
 Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5248
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_refine_ls_shift/su_max          0.007
_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 0.68513(12) 0.7059(2) 0.4242(2) 0.0423(6) Uani 1 1 d . . . . .
O2_1 O 0.51840(11) 0.8654(2) 0.47900(18) 0.0304(5) Uani 1 1 d . . . . .
O3_1 O 0.40846(13) 1.0138(3) 0.4478(3) 0.0503(7) Uani 1 1 d . . . . .
O4_1 O 0.66833(17) 0.8592(3) 0.2530(2) 0.0659(9) Uani 1 1 d . . . . .
O5_1 O 0.47054(15) 1.2029(3) 0.4313(3) 0.0589(8) Uani 1 1 d . . . . .
N1_1 N 0.61882(15) 0.7702(3) 0.4042(2) 0.0350(7) Uani 1 1 d . . . . .
C1_1 C 0.7467(2) 0.4949(4) 0.4142(3) 0.0442(9) Uani 1 1 d . . . . .
C2_1 C 0.7683(3) 0.3838(4) 0.3556(4) 0.0585(12) Uani 1 1 d . . . . .
H2_1 H 0.746911 0.365016 0.289246 0.070 Uiso 1 1 calc R U . . .
C3_1 C 0.8217(3) 0.3002(5) 0.3952(5) 0.0676(15) Uani 1 1 d . . . . .
H3_1 H 0.835538 0.225217 0.355443 0.081 Uiso 1 1 calc R U . . .
C4_1 C 0.8538(2) 0.3267(5) 0.4913(5) 0.0668(14) Uani 1 1 d . . . . .
H4_1 H 0.889874 0.270909 0.517230 0.080 Uiso 1 1 calc R U . . .
C5_1 C 0.8326(3) 0.4364(5) 0.5500(4) 0.0677(14) Uani 1 1 d . . . . .
H5_1 H 0.854523 0.455031 0.616002 0.081 Uiso 1 1 calc R U . . .
C6_1 C 0.7787(2) 0.5200(4) 0.5118(4) 0.0556(11) Uani 1 1 d . . . . .
H6_1 H 0.764224 0.593502 0.552772 0.067 Uiso 1 1 calc R U . . .
C7_1 C 0.6871(3) 0.5793(4) 0.3685(4) 0.0575(12) Uani 1 1 d . . . . .
H7A_1 H 0.694980 0.594004 0.291717 0.069 Uiso 1 1 calc R U . . .
H7B_1 H 0.641678 0.533232 0.377338 0.069 Uiso 1 1 calc R U . . .
C9_1 C 0.58586(17) 0.8105(3) 0.5101(3) 0.0320(8) Uani 1 1 d . . . . .
C10_1 C 0.53418(16) 0.9953(3) 0.4338(3) 0.0287(7) Uani 1 1 d . . . . .
C11_1 C 0.5612(2) 0.9687(4) 0.3156(3) 0.0364(9) Uani 1 1 d . . . . .
C12_1 C 0.6224(2) 0.8646(4) 0.3215(3) 0.0391(9) Uani 1 1 d . . . . .
C13_1 C 0.5722(2) 0.6896(4) 0.5802(3) 0.0378(9) Uani 1 1 d . . . . .
C14_1 C 0.5890(3) 0.6866(4) 0.6887(3) 0.0543(11) Uani 1 1 d . . . . .
H14_1 H 0.612175 0.759706 0.719912 0.065 Uiso 1 1 calc R U . . .
C15_1 C 0.5722(3) 0.5768(5) 0.7521(4) 0.0781(16) Uani 1 1 d . . . . .
H15_1 H 0.584843 0.575324 0.824972 0.094 Uiso 1 1 calc R U . . .
C16_1 C 0.5368(3) 0.4703(5) 0.7074(5) 0.0781(17) Uani 1 1 d . . . . .
H16_1 H 0.525225 0.396511 0.750113 0.094 Uiso 1 1 calc R U . . .
C17_1 C 0.5183(3) 0.4714(4) 0.6000(4) 0.0666(14) Uani 1 1 d . . . . .
H17_1 H 0.493956 0.398773 0.570118 0.080 Uiso 1 1 calc R U . . .
C18_1 C 0.5358(2) 0.5807(4) 0.5362(4) 0.0503(10) Uani 1 1 d . . . . .
H18_1 H 0.523158 0.581359 0.463275 0.060 Uiso 1 1 calc R U . . .
C19_1 C 0.62594(18) 0.9326(4) 0.5532(3) 0.0321(8) Uani 1 1 d . . . . .
C20_1 C 0.6215(2) 1.1720(4) 0.5240(3) 0.0429(9) Uani 1 1 d . . . . .
H20_1 H 0.601023 1.246928 0.491405 0.051 Uiso 1 1 calc R U . . .
C21_1 C 0.6801(2) 1.1837(5) 0.5931(4) 0.0554(12) Uani 1 1 d . . . . .
H21_1 H 0.698239 1.268386 0.608731 0.066 Uiso 1 1 calc R U . . .
C22_1 C 0.7115(2) 1.0728(5) 0.6385(4) 0.0540(11) Uani 1 1 d . . . . .
H22_1 H 0.750902 1.083871 0.683762 0.065 Uiso 1 1 calc R U . . .
C23_1 C 0.6860(2) 0.9448(4) 0.6185(3) 0.0432(10) Uani 1 1 d . . . . .
H23_1 H 0.708352 0.869702 0.647794 0.052 Uiso 1 1 calc R U . . .
C24_1 C 0.46764(18) 1.0832(4) 0.4377(3) 0.0338(8) Uani 1 1 d . . . . .
C25_1 C 0.3419(2) 1.0904(5) 0.4522(5) 0.0665(14) Uani 1 1 d . . . . .
H25A_1 H 0.341092 1.143724 0.516977 0.100 Uiso 1 1 calc R U . . .
H25B_1 H 0.301883 1.029839 0.452363 0.100 Uiso 1 1 calc R U . . .
H25C_1 H 0.338923 1.148131 0.390023 0.100 Uiso 1 1 calc R U . . .
C26_1 C 0.5892(2) 1.0960(4) 0.2613(3) 0.0510(11) Uani 1 1 d . . . . .
H26A_1 H 0.629064 1.130429 0.301937 0.076 Uiso 1 1 calc R U . . .
H26B_1 H 0.551798 1.162057 0.259010 0.076 Uiso 1 1 calc R U . . .
H26C_1 H 0.604443 1.075485 0.188854 0.076 Uiso 1 1 calc R U . . .
C27_1 C 0.5007(2) 0.9079(5) 0.2473(3) 0.0499(10) Uani 1 1 d . . . . .
H27A_1 H 0.465619 0.975703 0.231800 0.075 Uiso 1 1 calc R U . . .
H27B_1 H 0.478569 0.835889 0.286748 0.075 Uiso 1 1 calc R U . . .
H27C_1 H 0.520060 0.873947 0.180626 0.075 Uiso 1 1 calc R U . . .
C28_1 C 0.59482(17) 1.0441(3) 0.5057(3) 0.0302(8) 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
O1_1 N1_1 1.415(4) . ?
O1_1 C7_1 1.436(5) . ?
O2_1 C9_1 1.425(4) . ?
O2_1 C10_1 1.439(4) . ?
O3_1 C24_1 1.308(4) . ?
O3_1 C25_1 1.458(4) . ?
O4_1 C12_1 1.206(4) . ?
O5_1 C24_1 1.196(4) . ?
N1_1 C12_1 1.389(5) . ?
N1_1 C9_1 1.500(4) . ?
C1_1 C6_1 1.366(6) . ?
C1_1 C2_1 1.382(5) . ?
C1_1 C7_1 1.504(6) . ?
C2_1 C3_1 1.387(6) . ?
C3_1 C4_1 1.355(7) . ?
C4_1 C5_1 1.368(7) . ?
C5_1 C6_1 1.389(6) . ?
C9_1 C13_1 1.504(5) . ?
C9_1 C19_1 1.523(5) . ?
C10_1 C28_1 1.518(5) . ?
C10_1 C24_1 1.520(5) . ?
C10_1 C11_1 1.566(5) . ?
C11_1 C26_1 1.526(5) . ?
C11_1 C27_1 1.533(5) . ?
C11_1 C12_1 1.544(5) . ?
C13_1 C14_1 1.376(5) . ?
C13_1 C18_1 1.390(5) . ?
C14_1 C15_1 1.381(6) . ?
C15_1 C16_1 1.366(8) . ?
C16_1 C17_1 1.369(7) . ?
C17_1 C18_1 1.384(6) . ?
C19_1 C23_1 1.385(5) . ?
C19_1 C28_1 1.384(5) . ?
C20_1 C28_1 1.386(5) . ?
C20_1 C21_1 1.391(6) . ?
C21_1 C22_1 1.370(6) . ?
C22_1 C23_1 1.383(5) . ?

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_1 O1_1 C7_1 109.6(3) . . ?
C9_1 O2_1 C10_1 105.6(2) . . ?
C24_1 O3_1 C25_1 116.5(3) . . ?
C12_1 N1_1 O1_1 113.1(3) . . ?
C12_1 N1_1 C9_1 118.6(3) . . ?
O1_1 N1_1 C9_1 109.1(2) . . ?
C6_1 C1_1 C2_1 118.7(4) . . ?
C6_1 C1_1 C7_1 123.4(4) . . ?
C2_1 C1_1 C7_1 117.8(4) . . ?
C1_1 C2_1 C3_1 120.4(5) . . ?
C4_1 C3_1 C2_1 120.5(5) . . ?
C3_1 C4_1 C5_1 119.4(4) . . ?
C4_1 C5_1 C6_1 120.5(5) . . ?
C1_1 C6_1 C5_1 120.4(4) . . ?
O1_1 C7_1 C1_1 109.3(3) . . ?
O2_1 C9_1 N1_1 103.3(3) . . ?
O2_1 C9_1 C13_1 108.2(3) . . ?
N1_1 C9_1 C13_1 110.8(3) . . ?
O2_1 C9_1 C19_1 102.8(3) . . ?
N1_1 C9_1 C19_1 108.5(3) . . ?
C13_1 C9_1 C19_1 121.4(3) . . ?
O2_1 C10_1 C28_1 102.4(3) . . ?
O2_1 C10_1 C24_1 109.8(3) . . ?
C28_1 C10_1 C24_1 113.9(3) . . ?
O2_1 C10_1 C11_1 105.9(3) . . ?
C28_1 C10_1 C11_1 111.0(3) . . ?
C24_1 C10_1 C11_1 112.9(3) . . ?
C26_1 C11_1 C27_1 109.9(3) . . ?
C26_1 C11_1 C12_1 109.0(3) . . ?
C27_1 C11_1 C12_1 107.8(3) . . ?
C26_1 C11_1 C10_1 112.2(3) . . ?
C27_1 C11_1 C10_1 110.0(3) . . ?
C12_1 C11_1 C10_1 107.9(3) . . ?
O4_1 C12_1 N1_1 121.3(4) . . ?
O4_1 C12_1 C11_1 121.5(4) . . ?
N1_1 C12_1 C11_1 117.0(3) . . ?
C14_1 C13_1 C18_1 118.3(4) . . ?
C14_1 C13_1 C9_1 122.5(4) . . ?
C18_1 C13_1 C9_1 118.9(3) . . ?
C13_1 C14_1 C15_1 121.1(4) . . ?
C16_1 C15_1 C14_1 119.8(5) . . ?
C15_1 C16_1 C17_1 120.5(5) . . ?
C16_1 C17_1 C18_1 119.8(5) . . ?
C17_1 C18_1 C13_1 120.5(4) . . ?
C23_1 C19_1 C28_1 121.0(3) . . ?
C23_1 C19_1 C9_1 132.1(3) . . ?
C28_1 C19_1 C9_1 106.7(3) . . ?
C28_1 C20_1 C21_1 117.3(4) . . ?
C22_1 C21_1 C20_1 121.3(4) . . ?
C21_1 C22_1 C23_1 121.5(4) . . ?
C22_1 C23_1 C19_1 117.6(4) . . ?
O5_1 C24_1 O3_1 124.8(3) . . ?
O5_1 C24_1 C10_1 122.4(3) . . ?
O3_1 C24_1 C10_1 112.8(3) . . ?
C20_1 C28_1 C19_1 121.2(3) . . ?
C20_1 C28_1 C10_1 131.1(3) . . ?
C19_1 C28_1 C10_1 107.6(3) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043



