# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 2529718'
loop_
_audit_author_name
_audit_author_address
'Suresh Sundaram'
; University of Hyderabad
India
;
_audit_update_record             
;
2026-02-09 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H36 N2 O10'
_chemical_formula_weight         668.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.8296(9)
_cell_length_b                   21.2588(9)
_cell_length_c                   7.8763(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3990.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2015
_cell_measurement_theta_min      4.1660
_cell_measurement_theta_max      64.8960

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.675
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9407
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.785
_diffrn_reflns_theta_max         71.739
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_point_group_measured_fraction_full 0.829
_reflns_number_total             6283
_reflns_number_gt                3509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.455
_reflns_Friedel_fraction_max     0.576
_reflns_Friedel_fraction_full    0.608

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0857P)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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6283
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1925
_refine_ls_wR_factor_gt          0.1692
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.009

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
C36 C 0.9540(3) 1.1522(5) 0.937(2) 0.187(7) Uani 1 1 d . . . . .
H1 H 0.9816 1.1260 0.9818 0.225 Uiso 1 1 calc R U . . .
C17 C 0.5998(2) 0.8167(3) 0.6675(7) 0.0571(13) Uani 1 1 d . . . . .
C4 C 0.4543(2) 0.8821(3) 0.4724(7) 0.0575(13) Uani 1 1 d . . . . .
C14 C 0.5106(2) 0.9019(2) 0.4987(6) 0.0491(12) Uani 1 1 d . . . . .
C10 C 0.6889(2) 0.8356(3) 0.5285(7) 0.0638(14) Uani 1 1 d . . . . .
C32 C 0.7283(2) 1.0410(2) 0.6964(7) 0.0579(13) Uani 1 1 d . . . . .
C1 C 0.5189(2) 0.9229(3) 0.1990(7) 0.0603(14) Uani 1 1 d . . . . .
H15 H 0.5409 0.9354 0.1074 0.072 Uiso 1 1 calc R U . . .
C15 C 0.5424(2) 0.9203(2) 0.3613(7) 0.0533(13) Uani 1 1 d . . . . .
C2 C 0.4630(2) 0.9069(3) 0.1731(7) 0.0639(14) Uani 1 1 d . . . . .
C12 C 0.6030(2) 0.9385(2) 0.3849(7) 0.0581(14) Uani 1 1 d . . . . .
H18A H 0.6258 0.9165 0.3020 0.070 Uiso 1 1 calc R U . . .
H18B H 0.6072 0.9833 0.3648 0.070 Uiso 1 1 calc R U . . .
C3 C 0.4316(2) 0.8849(3) 0.3107(7) 0.0621(14) Uani 1 1 d . . . . .
H19 H 0.3948 0.8718 0.2932 0.075 Uiso 1 1 calc R U . . .
C16 C 0.6370(2) 0.8565(2) 0.5857(7) 0.0581(14) Uani 1 1 d . . . . .
C31 C 0.7344(2) 1.0688(2) 0.8796(6) 0.0514(12) Uani 1 1 d . . . . .
H22 H 0.7069 1.1025 0.8949 0.062 Uiso 1 1 calc R U . . .
C30 C 0.7270(3) 1.0437(3) 1.1908(7) 0.0591(14) Uani 1 1 d . . . . .
C6 C 0.5455(2) 0.8413(3) 0.7373(8) 0.0657(15) Uani 1 1 d . . . . .
H25A H 0.5155 0.8123 0.7090 0.079 Uiso 1 1 calc R U . . .
H25B H 0.5480 0.8437 0.8600 0.079 Uiso 1 1 calc R U . . .
C13 C 0.5789(2) 0.9435(3) 0.6827(7) 0.0608(14) Uani 1 1 d . . . . .
H26A H 0.5934 0.9418 0.7977 0.073 Uiso 1 1 calc R U . . .
H26B H 0.5681 0.9866 0.6587 0.073 Uiso 1 1 calc R U . . .
C33 C 0.7984(3) 1.1531(3) 0.8473(7) 0.0638(15) Uani 1 1 d . . . . .
C29 C 0.7244(2) 1.0189(2) 1.0104(6) 0.0538(13) Uani 1 1 d . . . . .
H29 H 0.6863 1.0028 0.9924 0.065 Uiso 1 1 calc R U . . .
C19 C 0.3703(2) 0.8388(3) 0.5906(9) 0.0799(18) Uani 1 1 d . . . . .
H30A H 0.3565 0.8233 0.6973 0.120 Uiso 1 1 calc R U . . .
H30B H 0.3703 0.8054 0.5087 0.120 Uiso 1 1 calc R U . . .
H30C H 0.3465 0.8722 0.5516 0.120 Uiso 1 1 calc R U . . .
C9 C 0.7024(3) 0.7726(3) 0.5505(8) 0.0797(19) Uani 1 1 d . . . . .
H31 H 0.7365 0.7574 0.5105 0.096 Uiso 1 1 calc R U . . .
C8 C 0.6655(3) 0.7321(3) 0.6315(8) 0.082(2) Uani 1 1 d . . . . .
C28 C 0.7417(3) 0.9090(3) 0.9805(7) 0.0657(15) Uani 1 1 d . . . . .
C34 C 0.8566(3) 1.1731(3) 0.8623(9) 0.0773(18) Uani 1 1 d . . . . .
C39 C 0.8702(3) 1.2348(3) 0.8282(9) 0.087(2) Uani 1 1 d . . . . .
H35 H 0.8420 1.2630 0.7988 0.104 Uiso 1 1 calc R U . . .
C27 C 0.7847(3) 0.8634(3) 0.9355(8) 0.0746(18) Uani 1 1 d . . . . .
C21 C 0.7783(3) 0.8628(4) 0.4093(10) 0.101(2) Uani 1 1 d . . . . .
H37A H 0.7976 0.8495 0.5101 0.151 Uiso 1 1 calc R U . . .
H37B H 0.7973 0.8984 0.3610 0.151 Uiso 1 1 calc R U . . .
H37C H 0.7778 0.8289 0.3286 0.151 Uiso 1 1 calc R U . . .
C26 C 0.7732(4) 0.8000(3) 0.9320(10) 0.102(2) Uani 1 1 d . . . . .
H38 H 0.7371 0.7865 0.9584 0.122 Uiso 1 1 calc R U . . .
C7 C 0.6140(3) 0.7548(3) 0.6843(8) 0.0749(17) Uani 1 1 d . . . . .
H39 H 0.5883 0.7271 0.7325 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4356(3) 0.9107(4) 0.0032(8) 0.095(2) Uani 1 1 d . . . . .
H40A H 0.4409 0.8718 -0.0563 0.142 Uiso 1 1 calc R U . . .
H40B H 0.4521 0.9444 -0.0609 0.142 Uiso 1 1 calc R U . . .
H40C H 0.3962 0.9185 0.0174 0.142 Uiso 1 1 calc R U . . .
C22 C 0.8378(3) 0.8809(4) 0.8948(15) 0.131(4) Uani 1 1 d . . . . .
H42 H 0.8474 0.9233 0.8978 0.158 Uiso 1 1 calc R U . . .
C38 C 0.9246(4) 1.2551(4) 0.8369(12) 0.112(3) Uani 1 1 d . . . . .
H43 H 0.9333 1.2964 0.8090 0.135 Uiso 1 1 calc R U . . .
C25 C 0.8131(5) 0.7561(4) 0.8909(12) 0.120(3) Uani 1 1 d . . . . .
H44 H 0.8037 0.7137 0.8897 0.144 Uiso 1 1 calc R U . . .
C35 C 0.8989(3) 1.1327(4) 0.9166(17) 0.146(5) Uani 1 1 d . . . . .
H45 H 0.8899 1.0910 0.9398 0.175 Uiso 1 1 calc R U . . .
C37 C 0.9656(4) 1.2154(6) 0.8855(19) 0.170(6) Uani 1 1 d . . . . .
H46 H 1.0026 1.2295 0.8856 0.204 Uiso 1 1 calc R U . . .
C23 C 0.8783(4) 0.8368(4) 0.849(2) 0.179(6) Uani 1 1 d . . . . .
H47 H 0.9139 0.8498 0.8155 0.215 Uiso 1 1 calc R U . . .
C24 C 0.8652(5) 0.7738(5) 0.8528(17) 0.154(5) Uani 1 1 d . . . . .
H49 H 0.8924 0.7438 0.8290 0.184 Uiso 1 1 calc R U . . .
C20 C 0.6798(4) 0.6620(3) 0.6500(11) 0.122(3) Uani 1 1 d . . . . .
H50A H 0.7055 0.6564 0.7427 0.184 Uiso 1 1 calc R U . . .
H50B H 0.6967 0.6471 0.5470 0.184 Uiso 1 1 calc R U . . .
H50C H 0.6461 0.6386 0.6719 0.184 Uiso 1 1 calc R U . . .
N5 N 0.53181(18) 0.9043(2) 0.6689(6) 0.0580(11) Uani 1 1 d . . . . .
N11 N 0.62373(18) 0.92316(19) 0.5603(5) 0.0562(11) Uani 1 1 d . . . . .
H1A H 0.6576 0.9480 0.5825 0.067 Uiso 1 1 calc R U . . .
O3 O 0.68354(17) 1.01386(18) 0.6746(5) 0.0736(12) Uani 1 1 d . . . . .
O4 O 0.76807(18) 1.04862(19) 0.5963(4) 0.0757(12) Uani 1 1 d . . . . .
O1 O 0.69981(18) 1.0899(2) 1.2280(5) 0.0835(13) Uani 1 1 d . . . . .
O2 O 0.75957(18) 1.01242(18) 1.2905(5) 0.0781(12) Uani 1 1 d . . . . .
H2 H 0.7590 1.0283 1.3853 0.117 Uiso 1 1 calc R U . . .
O8 O 0.7603(2) 1.1850(2) 0.7915(6) 0.0885(14) Uani 1 1 d . . . . .
O7 O 0.78976(14) 1.09371(15) 0.9051(4) 0.0566(9) Uani 1 1 d . . . . .
O6 O 0.76210(15) 0.96785(15) 0.9814(4) 0.0579(9) Uani 1 1 d . . . . .
O5 O 0.6930(2) 0.89731(19) 1.0073(7) 0.0985(16) Uani 1 1 d . . . . .
O9 O 0.42648(15) 0.8621(2) 0.6121(5) 0.0730(12) Uani 1 1 d . . . . .
O10 O 0.72191(16) 0.8800(2) 0.4515(6) 0.0808(12) 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
C36 C35 1.387(10) . ?
C36 C37 1.431(14) . ?
C17 C7 1.366(7) . ?
C17 C16 1.385(7) . ?
C17 C6 1.501(7) . ?
C4 O9 1.353(6) . ?
C4 C3 1.384(8) . ?
C4 C14 1.423(7) . ?
C14 C15 1.377(7) . ?
C14 N5 1.434(6) . ?
C10 O10 1.370(7) . ?
C10 C9 1.388(8) . ?
C10 C16 1.388(7) . ?
C32 O3 1.226(6) . ?
C32 O4 1.242(6) . ?
C32 C31 1.566(7) . ?
C1 C2 1.389(7) . ?
C1 C15 1.397(7) . ?
C15 C12 1.507(7) . ?
C2 C3 1.398(8) . ?
C2 C18 1.492(8) . ?
C12 N11 1.503(7) . ?
C16 N11 1.466(6) . ?
C31 O7 1.436(5) . ?
C31 C29 1.498(7) . ?
C30 O1 1.214(6) . ?
C30 O2 1.288(6) . ?
C30 C29 1.516(7) . ?
C6 N5 1.478(6) . ?
C13 N5 1.401(6) . ?
C13 N11 1.502(6) . ?
C33 O8 1.215(7) . ?
C33 O7 1.359(6) . ?
C33 C34 1.455(8) . ?
C29 O6 1.427(5) . ?
C19 O9 1.438(6) . ?
C9 C8 1.386(9) . ?
C8 C7 1.383(9) . ?
C8 C20 1.537(9) . ?
C28 O5 1.206(7) . ?
C28 O6 1.342(6) . ?
C28 C27 1.456(8) . ?
C34 C39 1.377(8) . ?
C34 C35 1.392(10) . ?
C39 C38 1.369(9) . ?
C27 C22 1.357(9) . ?
C27 C26 1.375(8) . ?
C21 O10 1.432(6) . ?
C26 C25 1.371(10) . ?
C22 C23 1.394(10) . ?
C38 C37 1.346(13) . ?
C25 C24 1.330(11) . ?
C23 C24 1.376(12) . ?

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
C35 C36 C37 115.5(10) . . ?
C7 C17 C16 118.4(6) . . ?
C7 C17 C6 120.9(6) . . ?
C16 C17 C6 120.7(5) . . ?
O9 C4 C3 124.8(5) . . ?
O9 C4 C14 115.9(5) . . ?
C3 C4 C14 119.3(5) . . ?
C15 C14 C4 119.3(5) . . ?
C15 C14 N5 122.1(4) . . ?
C4 C14 N5 118.6(5) . . ?
O10 C10 C9 125.9(6) . . ?
O10 C10 C16 115.7(5) . . ?
C9 C10 C16 118.4(6) . . ?
O3 C32 O4 129.5(5) . . ?
O3 C32 C31 112.7(5) . . ?
O4 C32 C31 117.8(5) . . ?
C2 C1 C15 120.6(5) . . ?
C14 C15 C1 120.6(5) . . ?
C14 C15 C12 120.2(5) . . ?
C1 C15 C12 119.2(5) . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 C18 122.6(6) . . ?
C3 C2 C18 118.6(5) . . ?
N11 C12 C15 111.8(4) . . ?
C4 C3 C2 121.3(5) . . ?
C17 C16 C10 121.7(5) . . ?
C17 C16 N11 121.0(5) . . ?
C10 C16 N11 117.3(5) . . ?
O7 C31 C29 108.2(4) . . ?
O7 C31 C32 110.7(4) . . ?
C29 C31 C32 110.7(4) . . ?
O1 C30 O2 126.3(5) . . ?
O1 C30 C29 119.1(5) . . ?
O2 C30 C29 114.6(5) . . ?
N5 C6 C17 111.8(5) . . ?
N5 C13 N11 110.4(4) . . ?
O8 C33 O7 121.7(6) . . ?
O8 C33 C34 125.4(6) . . ?
O7 C33 C34 112.9(6) . . ?
O6 C29 C31 109.1(4) . . ?
O6 C29 C30 112.8(4) . . ?
C31 C29 C30 113.1(4) . . ?
C8 C9 C10 120.6(6) . . ?
C9 C8 C7 119.1(6) . . ?
C9 C8 C20 120.3(7) . . ?
C7 C8 C20 120.4(7) . . ?
O5 C28 O6 122.7(6) . . ?
O5 C28 C27 125.7(6) . . ?
O6 C28 C27 111.6(5) . . ?
C39 C34 C35 118.5(6) . . ?
C39 C34 C33 119.1(7) . . ?
C35 C34 C33 122.3(6) . . ?
C38 C39 C34 120.9(8) . . ?
C22 C27 C26 116.8(7) . . ?
C22 C27 C28 122.1(6) . . ?
C26 C27 C28 121.1(7) . . ?
C25 C26 C27 122.1(8) . . ?
C17 C7 C8 121.7(6) . . ?
C27 C22 C23 121.4(7) . . ?
C37 C38 C39 120.3(8) . . ?
C24 C25 C26 120.6(9) . . ?
C36 C35 C34 122.5(8) . . ?
C38 C37 C36 121.9(9) . . ?
C24 C23 C22 119.4(9) . . ?
C25 C24 C23 119.5(9) . . ?
C13 N5 C14 112.0(4) . . ?
C13 N5 C6 109.5(4) . . ?
C14 N5 C6 112.7(4) . . ?
C16 N11 C12 114.0(4) . . ?
C16 N11 C13 110.1(4) . . ?
C12 N11 C13 107.1(4) . . ?
C33 O7 C31 115.9(4) . . ?
C28 O6 C29 118.7(4) . . ?
C4 O9 C19 117.9(5) . . ?
C10 O10 C21 117.8(5) . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.006 441 -6 ' '
2 0.500 0.500 -0.153 441 -6 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

