# 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. 
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#######################################################################

data_4Aa_a
_database_code_depnum_ccdc_archive 'CCDC 2447899'
loop_
_audit_author_name
_audit_author_address
'Sandeep Kaulage'
;IISER Pune
India
;
_audit_update_record             
;
2025-04-30 deposited with the CCDC.	2025-08-29 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         ?
_chemical_formula_sum            'C34 H28 N2 O4'
_chemical_formula_weight         528.58

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                   13.900(3)
_cell_length_b                   13.924(3)
_cell_length_c                   14.228(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.004(6)
_cell_angle_gamma                90
_cell_volume                     2693.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9423
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.38

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   0.5747
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            56471
_diffrn_reflns_av_unetI/netI     0.1577
_diffrn_reflns_av_R_equivalents  0.2082
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.069
_diffrn_reflns_theta_max         28.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6764
_reflns_number_gt                3700
_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 2014/5 (Sheldrick, 2014)'
_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)+(0.0186P)²+5.0124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6764
_refine_ls_number_parameters     366
_refine_ls_number_restraints     240
_refine_ls_R_factor_all          0.2140
_refine_ls_R_factor_gt           0.1151
_refine_ls_wR_factor_ref         0.1734
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.124
_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 0.92876(18) 0.53295(18) 0.13074(18) 0.0323(6) Uani 1 1 d . U . . .
N1 N 0.8327(2) 0.4195(2) 0.0382(2) 0.0239(7) Uani 1 1 d . U . . .
C1 C 0.5927(3) 0.2961(3) -0.0356(3) 0.0342(10) Uani 1 1 d . U . . .
H1 H 0.560239 0.245859 -0.074970 0.041 Uiso 1 1 calc R U . . .
O2 O 0.87130(15) 0.67118(16) 0.24889(17) 0.0207(6) Uani 1 1 d . U . . .
H2A H 0.8935(11) 0.633(2) 0.212(3) 0.031 Uiso 1 1 calc R U . . .
N2 N 0.6468(2) 0.5938(2) 0.4152(2) 0.0244(7) Uani 1 1 d . U . . .
C2 C 0.5411(3) 0.3487(3) 0.0197(3) 0.0320(9) Uani 1 1 d . U . . .
H2 H 0.473388 0.335453 0.016129 0.038 Uiso 1 1 calc R U . . .
O3 O 0.68409(18) 0.38475(16) 0.33728(17) 0.0282(6) Uani 1 1 d . U . . .
C3 C 0.5873(2) 0.4211(2) 0.0807(2) 0.0215(8) Uani 1 1 d . U . . .
H3 H 0.551911 0.457036 0.119092 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6854(2) 0.4390(2) 0.0839(2) 0.0160(7) Uani 1 1 d . U . . .
O4 O 0.57188(17) 0.55863(16) 0.26008(17) 0.0271(6) Uani 1 1 d . U . . .
C5 C 0.7349(2) 0.3871(2) 0.0249(2) 0.0210(8) Uani 1 1 d . U . . .
C6 C 0.6909(3) 0.3148(3) -0.0351(3) 0.0300(9) Uani 1 1 d . U . . .
H6 H 0.726097 0.279475 -0.074228 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8501(2) 0.4901(2) 0.1049(2) 0.0199(8) Uani 1 1 d . U . . .
C7 C 0.9060(3) 0.3800(3) -0.0114(3) 0.0380(10) Uani 1 1 d . U . . .
H7A H 0.884984 0.391332 -0.080666 0.057 Uiso 1 1 calc R U . . .
H7B H 0.912619 0.310800 0.000732 0.057 Uiso 1 1 calc R U . . .
H7C H 0.969483 0.411435 0.012294 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7571(2) 0.5063(2) 0.1453(2) 0.0143(7) Uani 1 1 d . U . . .
C10 C 0.7828(2) 0.4826(2) 0.2568(2) 0.0162(7) Uani 1 1 d . U . . .
H10 H 0.856082 0.477733 0.275508 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7531(2) 0.5711(2) 0.3093(2) 0.0150(7) Uani 1 1 d . U . . .
C13 C 0.7250(2) 0.6132(2) 0.1413(2) 0.0154(7) Uani 1 1 d . U . . .
H13A H 0.750194 0.647665 0.090588 0.018 Uiso 1 1 calc R U . . .
H13B H 0.652336 0.618193 0.127276 0.018 Uiso 1 1 calc R U . . .
C12 C 0.7681(2) 0.6555(2) 0.2393(2) 0.0171(7) Uani 1 1 d . U . . .
C14 C 0.7247(2) 0.7502(2) 0.2656(2) 0.0167(7) Uani 1 1 d . U . . .
C15 C 0.6263(2) 0.7742(2) 0.2317(2) 0.0231(8) Uani 1 1 d . U . . .
H15 H 0.584471 0.730703 0.190914 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5883(3) 0.8608(3) 0.2567(3) 0.0302(9) Uani 1 1 d . U . . .
H16 H 0.521139 0.876206 0.232419 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6479(3) 0.9239(3) 0.3164(3) 0.0342(10) Uani 1 1 d . U . . .
H17 H 0.622492 0.983328 0.333249 0.041 Uiso 1 1 calc R U . . .
C18 C 0.7448(3) 0.9000(3) 0.3515(3) 0.0341(10) Uani 1 1 d . U . . .
H18 H 0.785981 0.943242 0.393429 0.041 Uiso 1 1 calc R U . . .
C19 C 0.7835(3) 0.8140(2) 0.3269(2) 0.0256(8) Uani 1 1 d . U . . .
H19 H 0.850530 0.798717 0.352116 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5582(3) 0.6059(3) 0.4531(3) 0.0495(12) Uani 1 1 d . U . . .
H20A H 0.546956 0.674457 0.462357 0.074 Uiso 1 1 calc R U . . .
H20B H 0.565958 0.572510 0.514884 0.074 Uiso 1 1 calc R U . . .
H20C H 0.501856 0.578992 0.407737 0.074 Uiso 1 1 calc R U . . .
C21 C 0.6464(2) 0.5708(2) 0.3224(2) 0.0210(8) Uani 1 1 d . U . . .
C22 C 0.8094(2) 0.5863(2) 0.4105(2) 0.0179(7) Uani 1 1 d . U . . .
C23 C 0.7426(3) 0.6029(2) 0.4700(2) 0.0217(8) Uani 1 1 d . U . . .
C24 C 0.7730(3) 0.6254(3) 0.5658(3) 0.0338(10) Uani 1 1 d . U . . .
H24 H 0.726966 0.635971 0.605668 0.041 Uiso 1 1 calc R U . . .
C25 C 0.8738(3) 0.6321(3) 0.6019(3) 0.0368(10) Uani 1 1 d . U . . .
H25 H 0.896813 0.648785 0.667506 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9407(3) 0.6152(3) 0.5457(3) 0.0327(9) Uani 1 1 d . U . . .
H26 H 1.009064 0.619838 0.572579 0.039 Uiso 1 1 calc R U . . .
C27 C 0.9090(3) 0.5911(2) 0.4486(2) 0.0231(8) Uani 1 1 d . U . . .
H27 H 0.955323 0.578190 0.409645 0.028 Uiso 1 1 calc R U . . .
C28 C 0.7419(2) 0.3871(2) 0.2837(2) 0.0171(7) Uani 1 1 d . U . . .
C29 C 0.7744(2) 0.2974(2) 0.2427(2) 0.0179(7) Uani 1 1 d . U . . .
C30 C 0.8684(3) 0.2872(2) 0.2240(2) 0.0249(8) Uani 1 1 d . U . . .
H30 H 0.914012 0.338780 0.237343 0.030 Uiso 1 1 calc R U . . .
C31 C 0.8956(3) 0.2025(3) 0.1861(3) 0.0370(10) Uani 1 1 d . U . . .
H31 H 0.960125 0.195502 0.174648 0.044 Uiso 1 1 calc R U . . .
C32 C 0.8288(3) 0.1279(3) 0.1648(3) 0.0408(11) Uani 1 1 d . U . . .
H32 H 0.846942 0.070328 0.137228 0.049 Uiso 1 1 calc R U . . .
C33 C 0.7361(3) 0.1373(3) 0.1838(3) 0.0359(10) Uani 1 1 d . U . . .
H33 H 0.690831 0.085563 0.170109 0.043 Uiso 1 1 calc R U . . .
C34 C 0.7083(3) 0.2210(2) 0.2223(2) 0.0253(8) Uani 1 1 d . U . . .
H34 H 0.644145 0.226730 0.235054 0.030 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 1.233(4) . ?
N1 C8 1.352(4) . ?
N1 C5 1.408(4) . ?
N1 C7 1.462(4) . ?
C1 C2 1.379(5) . ?
C1 C6 1.388(5) . ?
C1 H1 0.9500 . ?
O2 C12 1.430(4) . ?
O2 H2A 0.85(4) . ?
N2 C21 1.358(4) . ?
N2 C23 1.401(4) . ?
N2 C20 1.454(5) . ?
C2 C3 1.397(5) . ?
C2 H2 0.9500 . ?
O3 C28 1.218(4) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 C9 1.506(4) . ?
O4 C21 1.226(4) . ?
C5 C6 1.379(5) . ?
C6 H6 0.9500 . ?
C8 C9 1.537(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C13 1.552(4) . ?
C9 C10 1.586(4) . ?
C10 C28 1.526(4) . ?
C10 C11 1.541(4) . ?
C10 H10 1.0000 . ?
C11 C22 1.504(4) . ?
C11 C21 1.533(4) . ?
C11 C12 1.583(4) . ?
C13 C12 1.518(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 C14 1.528(4) . ?
C14 C19 1.385(4) . ?
C14 C15 1.393(5) . ?
C15 C16 1.391(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 C27 1.379(5) . ?
C22 C23 1.400(5) . ?
C23 C24 1.377(5) . ?
C24 C25 1.392(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.368(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.400(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.488(5) . ?
C29 C30 1.394(5) . ?
C29 C34 1.396(5) . ?
C30 C31 1.381(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.377(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(5) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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 N1 C5 110.7(3) . . ?
C8 N1 C7 124.8(3) . . ?
C5 N1 C7 124.4(3) . . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C12 O2 H2A 109.5 . . ?
C21 N2 C23 112.0(3) . . ?
C21 N2 C20 123.7(3) . . ?
C23 N2 C20 124.3(3) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C9 131.5(3) . . ?
C5 C4 C9 108.8(3) . . ?
C6 C5 C4 122.9(3) . . ?
C6 C5 N1 127.4(3) . . ?
C4 C5 N1 109.7(3) . . ?
C5 C6 C1 116.6(3) . . ?
C5 C6 H6 121.7 . . ?
C1 C6 H6 121.7 . . ?
O1 C8 N1 125.4(3) . . ?
O1 C8 C9 125.5(3) . . ?
N1 C8 C9 109.1(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C9 C8 101.5(2) . . ?
C4 C9 C13 115.1(3) . . ?
C8 C9 C13 112.7(3) . . ?
C4 C9 C10 115.8(2) . . ?
C8 C9 C10 108.1(2) . . ?
C13 C9 C10 103.8(2) . . ?
C28 C10 C11 115.0(3) . . ?
C28 C10 C9 114.5(2) . . ?
C11 C10 C9 106.9(2) . . ?
C28 C10 H10 106.6 . . ?
C11 C10 H10 106.6 . . ?
C9 C10 H10 106.6 . . ?
C22 C11 C21 102.0(3) . . ?
C22 C11 C10 116.0(3) . . ?
C21 C11 C10 114.9(3) . . ?
C22 C11 C12 112.8(3) . . ?
C21 C11 C12 109.6(2) . . ?
C10 C11 C12 101.8(2) . . ?
C12 C13 C9 106.5(2) . . ?
C12 C13 H13A 110.4 . . ?
C9 C13 H13A 110.4 . . ?
C12 C13 H13B 110.4 . . ?
C9 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
O2 C12 C13 110.1(3) . . ?
O2 C12 C14 106.5(2) . . ?
C13 C12 C14 117.4(3) . . ?
O2 C12 C11 108.3(2) . . ?
C13 C12 C11 102.1(2) . . ?
C14 C12 C11 112.1(3) . . ?
C19 C14 C15 118.2(3) . . ?
C19 C14 C12 119.7(3) . . ?
C15 C14 C12 122.1(3) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.3(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 121.2(4) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 120.2(3) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 N2 124.6(3) . . ?
O4 C21 C11 127.3(3) . . ?
N2 C21 C11 108.0(3) . . ?
C27 C22 C23 119.5(3) . . ?
C27 C22 C11 131.6(3) . . ?
C23 C22 C11 108.8(3) . . ?
C24 C23 C22 122.1(3) . . ?
C24 C23 N2 129.1(3) . . ?
C22 C23 N2 108.8(3) . . ?
C23 C24 C25 117.3(4) . . ?
C23 C24 H24 121.4 . . ?
C25 C24 H24 121.4 . . ?
C26 C25 C24 121.8(4) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 120.4(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 118.9(3) . . ?
C22 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
O3 C28 C29 121.1(3) . . ?
O3 C28 C10 120.7(3) . . ?
C29 C28 C10 118.2(3) . . ?
C30 C29 C34 119.0(3) . . ?
C30 C29 C28 122.2(3) . . ?
C34 C29 C28 118.8(3) . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.1(4) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 119.9(4) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.7(4) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C29 120.1(3) . . ?
C33 C34 H34 120.0 . . ?
C29 C34 H34 120.0 . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.071

# start Validation Reply Form
_vrf_RINTA01_4Aa_a               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal was of bad quality, multiple attempt of obtaining
good data was failed.
;
_vrf_PLAT020_4Aa_a               
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.208 Report
RESPONSE: The crystal was of bad quality, multiple attempt of obtaining
good data was failed.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_A4_a
_database_code_depnum_ccdc_archive 'CCDC 2447900'
loop_
_audit_author_name
_audit_author_address
'Sandeep Kaulage'
;IISER Pune
India
;
_audit_update_record             
;
2025-04-30 deposited with the CCDC.	2025-08-29 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         ?
_chemical_formula_sum            'C72 H66 F6 N6 O12'
_chemical_formula_weight         1321.30

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'
F F 0.0171 0.0103 '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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   11.106(3)
_cell_length_b                   11.106(3)
_cell_length_c                   14.374(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1535.5(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9749
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.03

_exptl_crystal_description       Irregular
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             690
_exptl_transmission_factor_min   0.6391
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.110
_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      296(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            37274
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.117
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5101
_reflns_number_gt                3926
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_chemical_absolute_configuration S
_refine_ls_number_reflns         5101
_refine_ls_number_parameters     295
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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
F1 F 0.1627(3) 0.2881(3) 0.10810(19) 0.0466(8) Uani 1 1 d . . . . .
C1 C 0.2747(5) 0.3734(5) 0.1614(3) 0.0299(10) Uani 1 1 d . . . . .
N1 N 0.1838(4) 0.2305(3) 0.3073(2) 0.0210(7) Uani 1 1 d . . . . .
O1 O 0.2042(3) 0.4626(3) 0.4528(2) 0.0278(7) Uani 1 1 d . . . . .
F2 F 0.4873(3) 0.4630(3) 0.89331(16) 0.0286(6) Uani 1 1 d . . . . .
C2 C 0.3826(6) 0.4916(5) 0.1221(3) 0.0341(11) Uani 1 1 d . . . . .
H2 H 0.378605 0.512229 0.059829 0.041 Uiso 1 1 calc R U . . .
N2 N 0.5929(3) 0.5088(3) 0.6988(2) 0.0176(7) Uani 1 1 d . . . . .
O2 O 0.1638(3) 0.1622(3) 0.45961(19) 0.0239(7) Uani 1 1 d . . . . .
O3 O 0.6217(3) 0.4123(4) 0.3954(2) 0.0268(7) Uani 1 1 d . . . . .
H3A H 0.653(3) 0.464(5) 0.437(4) 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4969(6) 0.5794(5) 0.1757(3) 0.0318(11) Uani 1 1 d . . . . .
H3 H 0.568697 0.659945 0.149399 0.038 Uiso 1 1 calc R U . . .
O4 O 0.7026(3) 0.5679(3) 0.55800(19) 0.0277(7) Uani 1 1 d . . . . .
C4 C 0.5053(5) 0.5484(4) 0.2685(3) 0.0237(9) Uani 1 1 d . . . . .
H4 H 0.582495 0.607254 0.304242 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3806(4) 0.3644(4) 0.4010(3) 0.0146(7) Uani 1 1 d . . . . .
C8 C 0.2303(4) 0.2418(4) 0.3967(3) 0.0173(8) Uani 1 1 d . . . . .
C7 C 0.0470(5) 0.1215(5) 0.2768(3) 0.0289(10) Uani 1 1 d . . . . .
H7A H -0.003993 0.162872 0.251863 0.043 Uiso 1 1 calc R U . . .
H7B H -0.002627 0.063519 0.328800 0.043 Uiso 1 1 calc R U . . .
H7C H 0.057626 0.066188 0.229712 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2803(4) 0.3415(4) 0.2539(3) 0.0198(8) Uani 1 1 d . . . . .
C5 C 0.3983(4) 0.4300(4) 0.3064(3) 0.0193(8) Uani 1 1 d . . . . .
C10 C 0.4102(4) 0.4579(4) 0.4869(2) 0.0133(7) Uani 1 1 d . . . . .
H10 H 0.493719 0.546029 0.471364 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2985(4) 0.4949(4) 0.5068(3) 0.0175(8) Uani 1 1 d . . . . .
C12 C 0.3131(5) 0.5790(5) 0.5922(3) 0.0255(9) Uani 1 1 d . . . . .
H12A H 0.409209 0.631145 0.609874 0.038 Uiso 1 1 calc R U . . .
H12B H 0.259957 0.517975 0.642024 0.038 Uiso 1 1 calc R U . . .
H12C H 0.279417 0.641806 0.579154 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4840(4) 0.3068(4) 0.4172(3) 0.0189(8) Uani 1 1 d . . . . .
C14 C 0.4543(6) 0.1839(5) 0.3557(3) 0.0308(11) Uani 1 1 d . . . . .
H14A H 0.464938 0.211732 0.291609 0.046 Uiso 1 1 calc R U . . .
H14B H 0.360972 0.109906 0.366252 0.046 Uiso 1 1 calc R U . . .
H14C H 0.518379 0.152359 0.370289 0.046 Uiso 1 1 calc R U . . .
C15 C 0.4650(4) 0.2724(4) 0.5212(3) 0.0186(8) Uani 1 1 d . . . . .
H15A H 0.543564 0.266815 0.545413 0.022 Uiso 1 1 calc R U . . .
H15B H 0.380919 0.184221 0.531929 0.022 Uiso 1 1 calc R U . . .
C16 C 0.4548(4) 0.3933(4) 0.5690(3) 0.0149(7) Uani 1 1 d . . . . .
C17 C 0.5990(4) 0.5009(4) 0.6054(3) 0.0181(8) Uani 1 1 d . . . . .
C18 C 0.3691(4) 0.3465(4) 0.6565(3) 0.0153(8) Uani 1 1 d . . . . .
C19 C 0.2304(4) 0.2508(4) 0.6720(3) 0.0184(8) Uani 1 1 d . . . . .
H19 H 0.172090 0.202723 0.622561 0.022 Uiso 1 1 calc R U . . .
C20 C 0.1794(4) 0.2275(4) 0.7624(3) 0.0212(9) Uani 1 1 d . . . . .
H20 H 0.086338 0.163025 0.773339 0.025 Uiso 1 1 calc R U . . .
C21 C 0.2651(4) 0.2988(4) 0.8363(3) 0.0213(9) Uani 1 1 d . . . . .
H21 H 0.229802 0.283062 0.896469 0.026 Uiso 1 1 calc R U . . .
C22 C 0.4039(4) 0.3939(4) 0.8203(3) 0.0187(8) Uani 1 1 d . . . . .
C23 C 0.4572(4) 0.4185(4) 0.7315(3) 0.0163(8) Uani 1 1 d . . . . .
C24 C 0.7168(4) 0.5876(5) 0.7565(3) 0.0274(10) Uani 1 1 d . . . . .
H24A H 0.796710 0.637556 0.717288 0.041 Uiso 1 1 calc R U . . .
H24B H 0.729586 0.524818 0.795611 0.041 Uiso 1 1 calc R U . . .
H24C H 0.705259 0.652220 0.794570 0.041 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
F1 C1 1.361(5) . ?
C1 C6 1.385(6) . ?
C1 C2 1.381(7) . ?
N1 C8 1.367(5) . ?
N1 C6 1.392(5) . ?
N1 C7 1.458(5) . ?
O1 C11 1.206(5) . ?
F2 C22 1.356(5) . ?
C2 C3 1.384(7) . ?
C2 H2 0.9300 . ?
N2 C17 1.350(5) . ?
N2 C23 1.409(5) . ?
N2 C24 1.464(5) . ?
O2 C8 1.221(5) . ?
O3 C13 1.421(5) . ?
O3 H3A 0.78(6) . ?
C3 C4 1.393(6) . ?
C3 H3 0.9300 . ?
O4 C17 1.219(5) . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C9 C5 1.509(5) . ?
C9 C8 1.540(6) . ?
C9 C10 1.540(5) . ?
C9 C13 1.587(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C5 1.402(6) . ?
C10 C11 1.516(5) . ?
C10 C16 1.585(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.501(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.518(6) . ?
C13 C15 1.530(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.562(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.505(5) . ?
C16 C17 1.533(5) . ?
C18 C19 1.384(6) . ?
C18 C23 1.406(6) . ?
C19 C20 1.389(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
F1 C1 C6 120.3(4) . . ?
F1 C1 C2 119.2(4) . . ?
C6 C1 C2 120.5(4) . . ?
C8 N1 C6 110.5(3) . . ?
C8 N1 C7 123.2(3) . . ?
C6 N1 C7 126.2(3) . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C17 N2 C23 110.9(3) . . ?
C17 N2 C24 122.7(3) . . ?
C23 N2 C24 125.9(3) . . ?
C13 O3 H3A 109.5 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C5 C9 C8 102.3(3) . . ?
C5 C9 C10 117.7(3) . . ?
C8 C9 C10 113.6(3) . . ?
C5 C9 C13 112.4(3) . . ?
C8 C9 C13 109.4(3) . . ?
C10 C9 C13 101.6(3) . . ?
O2 C8 N1 124.5(4) . . ?
O2 C8 C9 127.3(3) . . ?
N1 C8 C9 108.2(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C6 N1 130.0(4) . . ?
C1 C6 C5 118.9(4) . . ?
N1 C6 C5 111.1(3) . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 C9 131.5(4) . . ?
C6 C5 C9 107.2(3) . . ?
C11 C10 C9 114.0(3) . . ?
C11 C10 C16 117.8(3) . . ?
C9 C10 C16 107.5(3) . . ?
C11 C10 H10 105.5 . . ?
C9 C10 H10 105.5 . . ?
C16 C10 H10 105.5 . . ?
O1 C11 C12 121.2(4) . . ?
O1 C11 C10 120.3(3) . . ?
C12 C11 C10 118.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 105.8(3) . . ?
O3 C13 C15 112.3(3) . . ?
C14 C13 C15 113.8(3) . . ?
O3 C13 C9 109.4(3) . . ?
C14 C13 C9 113.7(3) . . ?
C15 C13 C9 101.9(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 106.0(3) . . ?
C13 C15 H15A 110.5 . . ?
C16 C15 H15A 110.5 . . ?
C13 C15 H15B 110.5 . . ?
C16 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
C18 C16 C17 102.6(3) . . ?
C18 C16 C15 112.1(3) . . ?
C17 C16 C15 108.9(3) . . ?
C18 C16 C10 119.4(3) . . ?
C17 C16 C10 110.0(3) . . ?
C15 C16 C10 103.6(3) . . ?
O4 C17 N2 125.4(4) . . ?
O4 C17 C16 125.8(3) . . ?
N2 C17 C16 108.9(3) . . ?
C19 C18 C23 120.3(4) . . ?
C19 C18 C16 132.0(4) . . ?
C23 C18 C16 107.7(3) . . ?
C20 C19 C18 119.2(4) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C22 119.7(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
F2 C22 C21 119.2(4) . . ?
F2 C22 C23 120.1(4) . . ?
C21 C22 C23 120.7(4) . . ?
C22 C23 C18 119.3(4) . . ?
C22 C23 N2 130.7(4) . . ?
C18 C23 N2 109.9(3) . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.064

