# 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_mo_AR_69_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2380688'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR National Chemical Laboratory, Pune 
India
;
_audit_update_record             
;
2024-08-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_mo_AR_69_0m_a       
;
PROBLEM: D-H Bond Without Acceptor O1 --H1 . Please Check
RESPONSE: The hydroxy hydrogen atom is disordered over two positions with equal occupancy (50%). 
Additionally, it is shielded between the two tert-butyl groups and is not accessible to the cyano 
group to form O-H...N hydrogen bonds.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H33 N O'
_chemical_formula_sum            'C25 H33 N O'
_chemical_formula_weight         363.52

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.4787(5)
_cell_length_b                   9.9360(4)
_cell_length_c                   19.7801(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.907(2)
_cell_angle_gamma                90
_cell_volume                     2180.04(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    3730
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5489
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            31745
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_av_R_equivalents  0.1012
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.752
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5416
_reflns_number_gt                3003
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_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)+(0.0571P)²+0.4168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5416
_refine_ls_number_parameters     258
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.09420(13) 0.81215(17) 0.59432(8) 0.0629(4) Uani 1 1 d D . . . .
H1 H 0.058(4) 0.794(5) 0.626(2) 0.094 Uiso 0.5 1 d D U P . .
H1' H 0.095(5) 0.795(6) 0.5535(14) 0.094 Uiso 0.5 1 d D U P . .
N1 N 0.5732(2) 0.4182(2) 0.80066(11) 0.0852(7) Uani 1 1 d . . . . .
C1 C 0.45983(14) 0.72342(17) 0.66674(9) 0.0365(4) Uani 1 1 d . . . . .
C2 C 0.37337(15) 0.63594(17) 0.67861(9) 0.0384(4) Uani 1 1 d . . . . .
H2 H 0.398730 0.557192 0.703462 0.046 Uiso 1 1 calc R U . . .
C3 C 0.25025(15) 0.66048(17) 0.65506(9) 0.0371(4) Uani 1 1 d . . . . .
C4 C 0.21559(15) 0.78171(18) 0.61926(9) 0.0411(4) Uani 1 1 d . . . . .
C5 C 0.29957(16) 0.87378(18) 0.60562(9) 0.0408(4) Uani 1 1 d . . . . .
C6 C 0.42092(16) 0.84105(18) 0.63058(9) 0.0412(4) Uani 1 1 d . . . . .
H6 H 0.478310 0.900818 0.622600 0.049 Uiso 1 1 calc R U . . .
C7 C 0.59425(15) 0.69106(18) 0.68738(9) 0.0395(4) Uani 1 1 d . . . . .
H7 H 0.633726 0.776607 0.682409 0.047 Uiso 1 1 calc R U . . .
C8 C 0.62801(15) 0.59749(19) 0.63406(9) 0.0421(4) Uani 1 1 d . . . . .
C9 C 0.71559(18) 0.6380(2) 0.60144(11) 0.0581(5) Uani 1 1 d . . . . .
H9 H 0.755445 0.719307 0.614016 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7444(2) 0.5594(3) 0.55064(12) 0.0723(7) Uani 1 1 d . . . . .
H10 H 0.803116 0.588652 0.529264 0.087 Uiso 1 1 calc R U . . .
C11 C 0.6877(2) 0.4389(3) 0.53115(11) 0.0686(7) Uani 1 1 d . . . . .
H11 H 0.707089 0.386858 0.496505 0.082 Uiso 1 1 calc R U . . .
C12 C 0.6018(2) 0.3962(2) 0.56364(11) 0.0631(6) Uani 1 1 d . . . . .
H12 H 0.563408 0.313952 0.551363 0.076 Uiso 1 1 calc R U . . .
C13 C 0.57211(18) 0.4747(2) 0.61442(10) 0.0523(5) Uani 1 1 d . . . . .
H13 H 0.513598 0.444723 0.635796 0.063 Uiso 1 1 calc R U . . .
C14 C 0.64815(15) 0.64951(18) 0.76538(9) 0.0412(4) Uani 1 1 d . . . . .
C15 C 0.78559(17) 0.6360(2) 0.78119(11) 0.0610(6) Uani 1 1 d . . . . .
H15A H 0.817409 0.611616 0.829390 0.091 Uiso 1 1 calc R U . . .
H15B H 0.819740 0.720235 0.772269 0.091 Uiso 1 1 calc R U . . .
H15C H 0.805666 0.567550 0.751821 0.091 Uiso 1 1 calc R U . . .
C16 C 0.60345(18) 0.5181(2) 0.78246(10) 0.0509(5) Uani 1 1 d . . . . .
C17 C 0.6151(2) 0.7541(2) 0.81396(11) 0.0589(5) Uani 1 1 d . . . . .
H17A H 0.652056 0.730455 0.861717 0.088 Uiso 1 1 calc R U . . .
H17B H 0.529079 0.756553 0.806568 0.088 Uiso 1 1 calc R U . . .
H17C H 0.643232 0.841089 0.804112 0.088 Uiso 1 1 calc R U . . .
C18 C 0.15868(15) 0.55483(18) 0.66626(9) 0.0422(4) Uani 1 1 d . . . . .
C19 C 0.22252(19) 0.4321(2) 0.70586(12) 0.0589(6) Uani 1 1 d . . . . .
H19A H 0.163555 0.367731 0.711752 0.088 Uiso 1 1 calc R U . . .
H19B H 0.270703 0.459698 0.750916 0.088 Uiso 1 1 calc R U . . .
H19C H 0.273363 0.391936 0.679755 0.088 Uiso 1 1 calc R U . . .
C20 C 0.07670(19) 0.6111(2) 0.70977(12) 0.0621(6) Uani 1 1 d . . . . .
H20A H 0.031379 0.539028 0.722939 0.093 Uiso 1 1 calc R U . . .
H20B H 0.022316 0.675917 0.682506 0.093 Uiso 1 1 calc R U . . .
H20C H 0.125134 0.653687 0.751073 0.093 Uiso 1 1 calc R U . . .
C21 C 0.0831(2) 0.5044(2) 0.59530(11) 0.0644(6) Uani 1 1 d . . . . .
H21A H 0.023258 0.442416 0.602425 0.097 Uiso 1 1 calc R U . . .
H21B H 0.134571 0.459883 0.571003 0.097 Uiso 1 1 calc R U . . .
H21C H 0.044218 0.579390 0.568017 0.097 Uiso 1 1 calc R U . . .
C22 C 0.26094(19) 1.0036(2) 0.56277(10) 0.0548(5) Uani 1 1 d . . . . .
C23 C 0.1764(2) 1.0909(2) 0.59360(14) 0.0768(7) Uani 1 1 d . . . . .
H23A H 0.156954 1.171997 0.566648 0.115 Uiso 1 1 calc R U . . .
H23B H 0.215838 1.113368 0.641193 0.115 Uiso 1 1 calc R U . . .
H23C H 0.103789 1.041865 0.592169 0.115 Uiso 1 1 calc R U . . .
C24 C 0.3695(2) 1.0917(2) 0.56106(15) 0.0867(8) Uani 1 1 d . . . . .
H24A H 0.342125 1.172569 0.535283 0.130 Uiso 1 1 calc R U . . .
H24B H 0.421868 1.043372 0.538834 0.130 Uiso 1 1 calc R U . . .
H24C H 0.412582 1.114489 0.608003 0.130 Uiso 1 1 calc R U . . .
C25 C 0.1959(3) 0.9643(3) 0.48764(12) 0.0864(8) Uani 1 1 d . . . . .
H25A H 0.169007 1.044102 0.460787 0.130 Uiso 1 1 calc R U . . .
H25B H 0.127773 0.908646 0.488051 0.130 Uiso 1 1 calc R U . . .
H25C H 0.250307 0.915583 0.467006 0.130 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 C4 1.387(2) . ?
N1 C16 1.140(3) . ?
C1 C6 1.383(2) . ?
C1 C2 1.384(2) . ?
C1 C7 1.525(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.402(2) . ?
C3 C18 1.541(2) . ?
C4 C5 1.405(2) . ?
C5 C6 1.391(2) . ?
C5 C22 1.545(3) . ?
C7 C8 1.529(2) . ?
C7 C14 1.563(2) . ?
C8 C13 1.386(3) . ?
C8 C9 1.387(2) . ?
C9 C10 1.378(3) . ?
C10 C11 1.369(4) . ?
C11 C12 1.376(3) . ?
C12 C13 1.382(3) . ?
C14 C16 1.474(3) . ?
C14 C17 1.528(3) . ?
C14 C15 1.533(3) . ?
C18 C19 1.530(3) . ?
C18 C21 1.532(3) . ?
C18 C20 1.535(2) . ?
C22 C24 1.530(3) . ?
C22 C25 1.532(3) . ?
C22 C23 1.539(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
C6 C1 C2 117.92(16) . . ?
C6 C1 C7 119.10(15) . . ?
C2 C1 C7 122.84(15) . . ?
C1 C2 C3 122.97(16) . . ?
C2 C3 C4 116.85(15) . . ?
C2 C3 C18 120.27(15) . . ?
C4 C3 C18 122.85(15) . . ?
O1 C4 C3 119.72(16) . . ?
O1 C4 C5 117.78(16) . . ?
C3 C4 C5 122.48(16) . . ?
C6 C5 C4 116.97(16) . . ?
C6 C5 C22 120.64(17) . . ?
C4 C5 C22 122.35(16) . . ?
C1 C6 C5 122.79(16) . . ?
C1 C7 C8 111.22(14) . . ?
C1 C7 C14 115.86(13) . . ?
C8 C7 C14 114.47(14) . . ?
C13 C8 C9 117.64(18) . . ?
C13 C8 C7 123.17(16) . . ?
C9 C8 C7 119.15(17) . . ?
C10 C9 C8 120.9(2) . . ?
C11 C10 C9 121.0(2) . . ?
C10 C11 C12 118.9(2) . . ?
C11 C12 C13 120.3(2) . . ?
C12 C13 C8 121.19(19) . . ?
C16 C14 C17 107.52(15) . . ?
C16 C14 C15 106.03(16) . . ?
C17 C14 C15 109.91(16) . . ?
C16 C14 C7 112.81(15) . . ?
C17 C14 C7 109.98(15) . . ?
C15 C14 C7 110.47(14) . . ?
N1 C16 C14 175.0(2) . . ?
C19 C18 C21 106.99(17) . . ?
C19 C18 C20 106.58(16) . . ?
C21 C18 C20 110.40(16) . . ?
C19 C18 C3 111.21(15) . . ?
C21 C18 C3 109.70(15) . . ?
C20 C18 C3 111.81(15) . . ?
C24 C22 C25 108.7(2) . . ?
C24 C22 C23 106.63(19) . . ?
C25 C22 C23 109.18(19) . . ?
C24 C22 C5 111.68(17) . . ?
C25 C22 C5 108.58(17) . . ?
C23 C22 C5 111.99(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C1 C2 C3 -174.87(16) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C1 C2 C3 C18 176.33(15) . . . . ?
C2 C3 C4 O1 179.90(16) . . . . ?
C18 C3 C4 O1 2.1(3) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C18 C3 C4 C5 -176.09(15) . . . . ?
O1 C4 C5 C6 -179.51(16) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
O1 C4 C5 C22 -1.6(3) . . . . ?
C3 C4 C5 C22 176.67(16) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 175.49(16) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C22 C5 C6 C1 -177.35(16) . . . . ?
C6 C1 C7 C8 -96.09(18) . . . . ?
C2 C1 C7 C8 79.6(2) . . . . ?
C6 C1 C7 C14 130.90(17) . . . . ?
C2 C1 C7 C14 -53.4(2) . . . . ?
C1 C7 C8 C13 -54.7(2) . . . . ?
C14 C7 C8 C13 79.0(2) . . . . ?
C1 C7 C8 C9 122.92(18) . . . . ?
C14 C7 C8 C9 -103.38(19) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
C7 C8 C9 C10 -176.84(19) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C7 C8 C13 C12 177.01(18) . . . . ?
C1 C7 C14 C16 68.1(2) . . . . ?
C8 C7 C14 C16 -63.36(19) . . . . ?
C1 C7 C14 C17 -51.9(2) . . . . ?
C8 C7 C14 C17 176.62(15) . . . . ?
C1 C7 C14 C15 -173.39(16) . . . . ?
C8 C7 C14 C15 55.1(2) . . . . ?
C2 C3 C18 C19 1.4(2) . . . . ?
C4 C3 C18 C19 179.03(16) . . . . ?
C2 C3 C18 C21 -116.80(18) . . . . ?
C4 C3 C18 C21 60.9(2) . . . . ?
C2 C3 C18 C20 120.37(18) . . . . ?
C4 C3 C18 C20 -62.0(2) . . . . ?
C6 C5 C22 C24 -7.1(3) . . . . ?
C4 C5 C22 C24 175.07(19) . . . . ?
C6 C5 C22 C25 112.8(2) . . . . ?
C4 C5 C22 C25 -65.1(2) . . . . ?
C6 C5 C22 C23 -126.6(2) . . . . ?
C4 C5 C22 C23 55.6(2) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.037

