# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2jhg4n
_database_code_depnum_ccdc_archive 'CCDC 2338551'
loop_
_audit_author_name
_audit_author_address
'Sourav Kundu'
;IISER Bhopal
India
;
_audit_update_record             
;
2024-03-07 deposited with the CCDC.	2024-08-05 downloaded from the CCDC.
;
_audit_creation_date             2024-03-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H27 N O3'
_chemical_formula_sum            'C24 H27 N O3'
_chemical_formula_weight         377.46
_chemical_absolute_configuration syn
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.44500(10)
_cell_length_b                   10.94740(10)
_cell_length_c                   11.98780(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.5050(10)
_cell_angle_gamma                90
_cell_volume                     968.676(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    189
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.852
_cell_measurement_theta_min      3.706
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.92107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12042
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.133
_diffrn_reflns_theta_min         3.719
_diffrn_ambient_temperature      100(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                3264
_reflns_number_total             3340
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.11(11)
_refine_ls_extinction_coef       0.0067(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.1215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0801
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11), C9(H9)
1.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C7(H7A,H7B), C8(H8A,H8B)
1.c Aromatic/amide H refined with riding coordinates:
 N17(H17), C4(H4), C20(H20), C19(H19), C15(H15), C21(H21), C18(H18)
1.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C)
1.e Idealised tetrahedral OH refined as rotating group:
 O26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O23 O 0.15003(19) 0.42751(14) 0.83821(12) 0.0245(3) Uani 1 1 d . . . . .
O26 O 0.5097(2) 0.62270(16) 1.07737(12) 0.0281(4) Uani 1 1 d . . . . .
H26 H 0.4632 0.5579 1.0925 0.042 Uiso 1 1 calc R U . . .
O25 O 0.3197(2) 0.42303(15) 1.00585(13) 0.0302(4) Uani 1 1 d . . . . .
N17 N 0.7451(2) 0.55364(18) 0.28988(15) 0.0261(4) Uani 1 1 d . . . . .
H17 H 0.6975 0.5893 0.2292 0.031 Uiso 1 1 calc R U . . .
C22 C 0.2779(3) 0.4726(2) 0.91556(18) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.7915(3) 0.48650(19) 0.47079(17) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.7499(3) 0.47634(19) 0.58046(17) 0.0190(4) Uani 1 1 d . . . . .
H4 H 0.8278 0.4337 0.6337 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2988(3) 0.6465(2) 0.55711(18) 0.0228(5) Uani 1 1 d . . . . .
H13A H 0.2038 0.6331 0.4948 0.027 Uiso 1 1 calc R U . . .
H13B H 0.3154 0.7340 0.5661 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2385(3) 0.5945(2) 0.66345(17) 0.0214(4) Uani 1 1 d . . . . .
H12A H 0.1998 0.5105 0.6511 0.026 Uiso 1 1 calc R U . . .
H12B H 0.1373 0.6414 0.6842 0.026 Uiso 1 1 calc R U . . .
C20 C 1.2098(3) 0.3466(2) 0.3687(2) 0.0266(5) Uani 1 1 d . . . . .
H20 H 1.3114 0.2982 0.3894 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4729(3) 0.59042(19) 0.52872(17) 0.0200(4) Uani 1 1 d . . . . .
C5 C 0.5933(3) 0.52913(19) 0.61166(18) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.3990(3) 0.60076(19) 0.75817(17) 0.0187(4) Uani 1 1 d . . . . .
H11 H 0.4490 0.6828 0.7515 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5541(3) 0.51357(18) 0.73367(17) 0.0179(4) Uani 1 1 d . . . . .
C27 C 0.5128(3) 0.37729(18) 0.74930(18) 0.0210(5) Uani 1 1 d . . . . .
H27A H 0.4046 0.3554 0.7008 0.032 Uiso 1 1 calc R U . . .
H27B H 0.4956 0.3625 0.8261 0.032 Uiso 1 1 calc R U . . .
H27C H 0.6123 0.3289 0.7307 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5327(3) 0.6242(2) 0.96045(17) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.5651 0.7082 0.9431 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6736(3) 0.5523(2) 0.39106(18) 0.0218(5) Uani 1 1 d . . . . .
C19 C 1.1779(3) 0.3951(2) 0.25936(19) 0.0275(5) Uani 1 1 d . . . . .
H19 H 1.2605 0.3797 0.2092 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3547(3) 0.59449(19) 0.88199(17) 0.0206(4) Uani 1 1 d . . . . .
C7 C 0.7237(3) 0.55011(19) 0.81509(17) 0.0200(4) Uani 1 1 d . . . . .
H7A H 0.8227 0.4958 0.8038 0.024 Uiso 1 1 calc R U . . .
H7B H 0.7591 0.6325 0.7976 0.024 Uiso 1 1 calc R U . . .
C2 C 0.9389(3) 0.44291(19) 0.41356(16) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.6917(3) 0.5445(2) 0.93816(18) 0.0229(5) Uani 1 1 d . . . . .
H8A H 0.6682 0.4606 0.9579 0.027 Uiso 1 1 calc R U . . .
H8B H 0.8002 0.5714 0.9855 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5137(3) 0.6018(2) 0.41937(17) 0.0227(5) Uani 1 1 d . . . . .
H15 H 0.4344 0.6423 0.3654 0.027 Uiso 1 1 calc R U . . .
C21 C 1.0913(3) 0.37027(19) 0.44571(18) 0.0239(5) Uani 1 1 d . . . . .
H21 H 1.1127 0.3382 0.5181 0.029 Uiso 1 1 calc R U . . .
C1 C 0.9060(3) 0.4880(2) 0.30242(18) 0.0241(5) Uani 1 1 d . . . . .
C24 C 0.0751(3) 0.3113(2) 0.8664(2) 0.0317(5) Uani 1 1 d . . . . .
H24A H -0.0099 0.2835 0.8044 0.047 Uiso 1 1 calc R U . . .
H24B H 0.0146 0.3206 0.9318 0.047 Uiso 1 1 calc R U . . .
H24C H 0.1710 0.2526 0.8815 0.047 Uiso 1 1 calc R U . . .
C18 C 1.0260(3) 0.4654(2) 0.22460(18) 0.0266(5) Uani 1 1 d . . . . .
H18 H 1.0048 0.4965 0.1519 0.032 Uiso 1 1 calc R U . . .
C28 C 0.2128(3) 0.6919(2) 0.90135(19) 0.0263(5) Uani 1 1 d . . . . .
H28A H 0.0979 0.6701 0.8603 0.039 Uiso 1 1 calc R U . . .
H28B H 0.2503 0.7698 0.8757 0.039 Uiso 1 1 calc R U . . .
H28C H 0.2019 0.6965 0.9801 0.039 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
O23 C22 1.334(3) . ?
O23 C24 1.447(3) . ?
O26 C9 1.434(2) . ?
O25 C22 1.215(3) . ?
N17 C16 1.387(3) . ?
N17 C1 1.388(3) . ?
C22 C10 1.526(3) . ?
C3 C4 1.394(3) . ?
C3 C16 1.409(3) . ?
C3 C2 1.449(3) . ?
C4 C5 1.395(3) . ?
C13 C12 1.516(3) . ?
C13 C14 1.513(3) . ?
C12 C11 1.538(3) . ?
C20 C19 1.406(3) . ?
C20 C21 1.382(3) . ?
C14 C5 1.418(3) . ?
C14 C15 1.389(3) . ?
C5 C6 1.538(3) . ?
C11 C6 1.556(3) . ?
C11 C10 1.563(3) . ?
C6 C27 1.540(3) . ?
C6 C7 1.544(3) . ?
C9 C10 1.556(3) . ?
C9 C8 1.523(3) . ?
C16 C15 1.390(3) . ?
C19 C18 1.386(3) . ?
C10 C28 1.539(3) . ?
C7 C8 1.526(3) . ?
C2 C21 1.398(3) . ?
C2 C1 1.412(3) . ?
C1 C18 1.396(3) . ?

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
C22 O23 C24 115.18(17) . . ?
C16 N17 C1 108.92(17) . . ?
O23 C22 C10 113.48(17) . . ?
O25 C22 O23 122.0(2) . . ?
O25 C22 C10 124.37(19) . . ?
C4 C3 C16 119.02(18) . . ?
C4 C3 C2 134.09(19) . . ?
C16 C3 C2 106.89(18) . . ?
C3 C4 C5 121.08(18) . . ?
C14 C13 C12 113.14(17) . . ?
C13 C12 C11 108.51(16) . . ?
C21 C20 C19 120.5(2) . . ?
C5 C14 C13 121.09(19) . . ?
C15 C14 C13 118.37(18) . . ?
C15 C14 C5 120.53(18) . . ?
C4 C5 C14 118.82(19) . . ?
C4 C5 C6 118.57(17) . . ?
C14 C5 C6 122.56(18) . . ?
C12 C11 C6 110.95(16) . . ?
C12 C11 C10 117.33(16) . . ?
C6 C11 C10 113.96(16) . . ?
C5 C6 C11 110.46(16) . . ?
C5 C6 C27 106.79(17) . . ?
C5 C6 C7 109.34(16) . . ?
C27 C6 C11 113.99(16) . . ?
C27 C6 C7 109.51(16) . . ?
C7 C6 C11 106.72(16) . . ?
O26 C9 C10 112.81(16) . . ?
O26 C9 C8 111.07(17) . . ?
C8 C9 C10 113.24(16) . . ?
N17 C16 C3 108.81(18) . . ?
N17 C16 C15 130.42(19) . . ?
C15 C16 C3 120.76(19) . . ?
C18 C19 C20 121.5(2) . . ?
C22 C10 C11 114.92(17) . . ?
C22 C10 C9 110.02(17) . . ?
C22 C10 C28 106.12(17) . . ?
C9 C10 C11 107.23(16) . . ?
C28 C10 C11 110.28(17) . . ?
C28 C10 C9 108.11(17) . . ?
C8 C7 C6 112.50(17) . . ?
C21 C2 C3 133.98(19) . . ?
C21 C2 C1 119.59(19) . . ?
C1 C2 C3 106.43(18) . . ?
C9 C8 C7 111.70(17) . . ?
C14 C15 C16 119.69(18) . . ?
C20 C21 C2 119.2(2) . . ?
N17 C1 C2 108.91(19) . . ?
N17 C1 C18 129.7(2) . . ?
C18 C1 C2 121.4(2) . . ?
C19 C18 C1 117.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
