# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2063896'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2022-05-16 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         'C27 H29 N O4'
_chemical_formula_sum            'C27 H29 N O4'
_chemical_formula_weight         431.51

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                   9.0386(4)
_cell_length_b                   10.9319(5)
_cell_length_c                   13.2664(6)
_cell_angle_alpha                75.768(2)
_cell_angle_beta                 71.588(2)
_cell_angle_gamma                87.843(2)
_cell_volume                     1204.42(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9197
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      26.8

_exptl_crystal_description       'BLOCK TYPE'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      1.2
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   0.6832
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    0.079
_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-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'FINE FOCUS SEALED TUBE'
_diffrn_measurement_device_type  'BRUKER APEX-III.PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24228
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5296
_reflns_number_gt                3621
_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       'BRUKER APEX-III'
_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    ?
_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)+(0.0664P)²+0.3631P] 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         5296
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.60361(19) 0.38587(15) 0.65882(15) 0.0874(5) Uani 1 1 d . . . . .
C1 C 0.4924(3) -0.1455(2) 0.9130(2) 0.0936(8) Uani 1 1 d . . . . .
H1 H 0.570097 -0.100301 0.851817 0.112 Uiso 1 1 calc R U . . .
N1 N 0.13523(18) 0.29729(14) 0.79396(13) 0.0618(4) Uani 1 1 d . . . . .
O2 O 0.60205(16) 0.18905(14) 0.64210(15) 0.0798(5) Uani 1 1 d . . . . .
C2 C 0.5236(3) -0.2610(3) 0.9710(3) 0.1089(10) Uani 1 1 d . . . . .
H2 H 0.622236 -0.293174 0.949097 0.131 Uiso 1 1 calc R U . . .
O3 O 0.4659(2) 0.27812(16) 0.46753(13) 0.0874(5) Uani 1 1 d . . . . .
C3 C 0.4103(3) -0.3281(2) 1.0601(2) 0.0849(7) Uani 1 1 d . . . . .
H3 H 0.431378 -0.406217 1.098999 0.102 Uiso 1 1 calc R U . . .
O4 O 0.2556(2) 0.15803(16) 0.57624(15) 0.0937(5) Uani 1 1 d . . . . .
C4 C 0.2663(3) -0.2810(2) 1.09241(18) 0.0742(6) Uani 1 1 d . . . . .
H4 H 0.189297 -0.327303 1.153430 0.089 Uiso 1 1 calc R U . . .
C6 C 0.3464(2) -0.09591(17) 0.94493(15) 0.0556(4) Uani 1 1 d . . . . .
C5 C 0.2330(2) -0.16520(19) 1.03570(16) 0.0625(5) Uani 1 1 d . . . . .
H5 H 0.134086 -0.133877 1.058631 0.075 Uiso 1 1 calc R U . . .
C8 C 0.2847(2) 0.11786(17) 0.82684(16) 0.0585(5) Uani 1 1 d . . . . .
C7 C 0.3132(2) 0.02181(18) 0.88151(16) 0.0582(5) Uani 1 1 d . . . . .
C9 C 0.2565(2) 0.23597(16) 0.76118(15) 0.0550(4) Uani 1 1 d . . . . .
C10 C 0.3713(2) 0.29768(15) 0.64798(15) 0.0519(4) Uani 1 1 d . . . . .
C11 C 0.5388(2) 0.29843(18) 0.65002(15) 0.0569(5) Uani 1 1 d . . . . .
C12 C 0.7607(3) 0.1744(3) 0.6472(3) 0.1052(9) Uani 1 1 d . . . . .
H12A H 0.817528 0.255525 0.617822 0.126 Uiso 1 1 calc R U . . .
H12B H 0.757997 0.143330 0.722809 0.126 Uiso 1 1 calc R U . . .
C13 C 0.8376(3) 0.0876(4) 0.5852(3) 0.1295(12) Uani 1 1 d . . . . .
H13A H 0.846339 0.121366 0.509446 0.194 Uiso 1 1 calc R U . . .
H13B H 0.778341 0.008644 0.612257 0.194 Uiso 1 1 calc R U . . .
H13C H 0.939912 0.074332 0.592089 0.194 Uiso 1 1 calc R U . . .
C14 C 0.3564(2) 0.23282(18) 0.56213(17) 0.0599(5) Uani 1 1 d . . . . .
C15 C 0.4739(4) 0.2289(3) 0.3732(2) 0.1042(9) Uani 1 1 d . . . . .
H15A H 0.375698 0.185697 0.385336 0.125 Uiso 1 1 calc R U . . .
H15B H 0.493130 0.297798 0.307951 0.125 Uiso 1 1 calc R U . . .
C16 C 0.5977(5) 0.1429(4) 0.3585(3) 0.1352(13) Uani 1 1 d . . . . .
H16A H 0.610539 0.116290 0.292589 0.203 Uiso 1 1 calc R U . . .
H16B H 0.572694 0.070653 0.420043 0.203 Uiso 1 1 calc R U . . .
H16C H 0.692784 0.184166 0.353057 0.203 Uiso 1 1 calc R U . . .
C17 C 0.3075(2) 0.43107(16) 0.62839(16) 0.0595(5) Uani 1 1 d . . . . .
H17A H 0.368755 0.490192 0.644570 0.071 Uiso 1 1 calc R U . . .
H17B H 0.308105 0.461346 0.553111 0.071 Uiso 1 1 calc R U . . .
C18 C 0.1398(2) 0.41407(16) 0.70806(15) 0.0554(4) Uani 1 1 d . . . . .
H18 H 0.071046 0.398778 0.667827 0.067 Uiso 1 1 calc R U . . .
C19 C 0.0829(2) 0.52929(16) 0.75223(15) 0.0514(4) Uani 1 1 d . . . . .
C20 C 0.1323(2) 0.56004(19) 0.83341(16) 0.0609(5) Uani 1 1 d . . . . .
C21 C 0.2411(3) 0.4807(2) 0.8870(2) 0.0858(7) Uani 1 1 d . . . . .
H21A H 0.334089 0.467657 0.831354 0.129 Uiso 1 1 calc R U . . .
H21B H 0.190003 0.400583 0.929355 0.129 Uiso 1 1 calc R U . . .
H21C H 0.268271 0.523725 0.934070 0.129 Uiso 1 1 calc R U . . .
C22 C 0.0823(3) 0.6702(2) 0.86587(18) 0.0689(6) Uani 1 1 d . . . . .
H22 H 0.113543 0.689076 0.920928 0.083 Uiso 1 1 calc R U . . .
C23 C -0.0112(2) 0.75242(19) 0.82031(18) 0.0630(5) Uani 1 1 d . . . . .
C24 C -0.0557(3) 0.8747(2) 0.8546(2) 0.0916(8) Uani 1 1 d . . . . .
H24A H 0.030250 0.935531 0.819421 0.137 Uiso 1 1 calc R U . . .
H24B H -0.081048 0.859209 0.932676 0.137 Uiso 1 1 calc R U . . .
H24C H -0.144671 0.906730 0.833319 0.137 Uiso 1 1 calc R U . . .
C25 C -0.0587(2) 0.72061(18) 0.74101(17) 0.0608(5) Uani 1 1 d . . . . .
H25 H -0.123007 0.774487 0.709568 0.073 Uiso 1 1 calc R U . . .
C26 C -0.0143(2) 0.61057(17) 0.70589(16) 0.0547(4) Uani 1 1 d . . . . .
C27 C -0.0708(3) 0.5851(2) 0.6172(2) 0.0812(7) Uani 1 1 d . . . . .
H27A H -0.122190 0.657513 0.588663 0.122 Uiso 1 1 calc R U . . .
H27B H -0.142688 0.513106 0.647172 0.122 Uiso 1 1 calc R U . . .
H27C H 0.016581 0.568523 0.559236 0.122 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 C11 1.188(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.386(3) . ?
C1 H1 0.9300 . ?
N1 C9 1.275(2) . ?
N1 C18 1.480(2) . ?
O2 C11 1.319(2) . ?
O2 C12 1.457(3) . ?
C2 C3 1.360(4) . ?
C2 H2 0.9300 . ?
O3 C14 1.322(2) . ?
O3 C15 1.461(3) . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
O4 C14 1.185(2) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C6 C5 1.380(3) . ?
C6 C7 1.432(3) . ?
C5 H5 0.9300 . ?
C8 C7 1.191(3) . ?
C8 C9 1.433(3) . ?
C9 C10 1.536(2) . ?
C10 C11 1.523(3) . ?
C10 C14 1.523(3) . ?
C10 C17 1.540(2) . ?
C12 C13 1.425(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.430(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.536(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.522(2) . ?
C18 H18 0.9800 . ?
C19 C26 1.397(2) . ?
C19 C20 1.402(3) . ?
C20 C22 1.390(3) . ?
C20 C21 1.516(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C23 C25 1.374(3) . ?
C23 C24 1.516(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.395(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.508(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C9 N1 C18 108.92(15) . . ?
C11 O2 C12 117.43(18) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C14 O3 C15 119.5(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C5 C6 C1 118.47(18) . . ?
C5 C6 C7 121.25(18) . . ?
C1 C6 C7 120.22(18) . . ?
C4 C5 C6 120.00(19) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C8 C9 177.5(2) . . ?
C8 C7 C6 178.1(2) . . ?
N1 C9 C8 121.96(17) . . ?
N1 C9 C10 115.82(15) . . ?
C8 C9 C10 122.21(16) . . ?
C11 C10 C14 111.10(15) . . ?
C11 C10 C9 111.77(15) . . ?
C14 C10 C9 110.63(15) . . ?
C11 C10 C17 112.72(15) . . ?
C14 C10 C17 109.84(15) . . ?
C9 C10 C17 100.33(14) . . ?
O1 C11 O2 124.32(19) . . ?
O1 C11 C10 124.33(18) . . ?
O2 C11 C10 111.35(16) . . ?
C13 C12 O2 109.6(2) . . ?
C13 C12 H12A 109.7 . . ?
O2 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
O2 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 O3 124.8(2) . . ?
O4 C14 C10 124.9(2) . . ?
O3 C14 C10 110.13(16) . . ?
C16 C15 O3 108.8(3) . . ?
C16 C15 H15A 109.9 . . ?
O3 C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
O3 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C10 104.00(14) . . ?
C18 C17 H17A 111.0 . . ?
C10 C17 H17A 111.0 . . ?
C18 C17 H17B 111.0 . . ?
C10 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
N1 C18 C19 114.10(15) . . ?
N1 C18 C17 106.21(14) . . ?
C19 C18 C17 113.82(14) . . ?
N1 C18 H18 107.5 . . ?
C19 C18 H18 107.5 . . ?
C17 C18 H18 107.5 . . ?
C26 C19 C20 119.10(16) . . ?
C26 C19 C18 118.85(16) . . ?
C20 C19 C18 121.95(16) . . ?
C22 C20 C19 118.95(17) . . ?
C22 C20 C21 117.49(19) . . ?
C19 C20 C21 123.55(18) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 122.96(19) . . ?
C23 C22 H22 118.5 . . ?
C20 C22 H22 118.5 . . ?
C22 C23 C25 117.27(18) . . ?
C22 C23 C24 120.9(2) . . ?
C25 C23 C24 121.83(19) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 C26 122.51(17) . . ?
C23 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C25 C26 C19 119.19(17) . . ?
C25 C26 C27 118.45(17) . . ?
C19 C26 C27 122.35(17) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.032

