# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_TS33_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1979508'
loop_
_audit_author_name
_audit_author_address
'TANDRIM SHYAM'
;The University of Burdwan
India
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2023-06-06 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            'C25 H30 N2 O'
_chemical_formula_weight         374.51

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                   9.602(7)
_cell_length_b                   9.726(8)
_cell_length_c                   13.486(12)
_cell_angle_alpha                68.55(3)
_cell_angle_beta                 73.114(19)
_cell_angle_gamma                68.923(18)
_cell_volume                     1075.4(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4061
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      28.377

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7031
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20048
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.650
_diffrn_reflns_theta_max         28.377
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5372
_reflns_number_gt                4061
_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)+(0.1000P)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_number_reflns         5323
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_restrained_S_all      1.222
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.080

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
O001 O 0.35927(9) 0.79617(10) 0.49411(7) 0.0506(3) Uani 1 1 d . . . . .
H001 H 0.422211 0.830316 0.444275 0.076 Uiso 1 1 calc R U . . .
N002 N 0.10268(10) 0.58624(12) 0.76412(8) 0.0455(3) Uani 1 1 d . . . . .
N003 N 0.62431(11) 0.82219(12) 0.38883(8) 0.0446(3) Uani 1 1 d . . . . .
C18 C 0.43060(12) 0.66703(13) 0.56285(9) 0.0376(3) Uani 1 1 d . . . . .
C5 C -0.06383(12) 0.64556(13) 0.78885(9) 0.0396(3) Uani 1 1 d . . . . .
C12 C 0.34503(12) 0.58735(13) 0.65354(9) 0.0371(3) Uani 1 1 d . . . . .
C13 C 0.41970(13) 0.45293(13) 0.72258(9) 0.0396(3) Uani 1 1 d . . . . .
H13 H 0.362219 0.400440 0.782884 0.048 Uiso 1 1 calc R U . . .
C11 C 0.17877(12) 0.64591(13) 0.67604(9) 0.0389(3) Uani 1 1 d . . . . .
H11 H 0.129115 0.728308 0.624371 0.047 Uiso 1 1 calc R U . . .
C17 C 0.58982(13) 0.61343(13) 0.54637(9) 0.0402(3) Uani 1 1 d . . . . .
C15 C 0.57610(13) 0.39303(14) 0.70597(10) 0.0429(3) Uani 1 1 d . . . . .
C23 C 0.72009(12) 0.91084(14) 0.30056(9) 0.0413(3) Uani 1 1 d . . . . .
C19 C 0.68210(13) 0.70092(14) 0.45832(10) 0.0449(3) Uani 1 1 d . . . . .
H19 H 0.787027 0.666674 0.452883 0.054 Uiso 1 1 calc R U . . .
C6 C -0.10235(14) 0.71391(17) 0.88261(10) 0.0501(3) Uani 1 1 d . . . . .
H6A H -0.045001 0.641557 0.938488 0.060 Uiso 1 1 calc R U . . .
H6AB H -0.071743 0.807727 0.856616 0.060 Uiso 1 1 calc R U . . .
C3 C -0.13067(13) 0.76262(15) 0.69660(10) 0.0469(3) Uani 1 1 d . . . . .
C16 C 0.65876(13) 0.47729(15) 0.61785(10) 0.0454(3) Uani 1 1 d . . . . .
H16 H 0.764186 0.441338 0.606192 0.054 Uiso 1 1 calc R U . . .
C10 C -0.12641(13) 0.50638(15) 0.82598(11) 0.0496(3) Uani 1 1 d . . . . .
H10A H -0.109937 0.469454 0.764550 0.060 Uiso 1 1 calc R U . . .
H10B H -0.071123 0.423988 0.879644 0.060 Uiso 1 1 calc R U . . .
C28 C 0.62498(14) 1.07849(14) 0.27108(11) 0.0489(3) Uani 1 1 d . . . . .
H28A H 0.528567 1.084195 0.258092 0.059 Uiso 1 1 calc R U . . .
H28B H 0.604281 1.118653 0.331584 0.059 Uiso 1 1 calc R U . . .
C29 C 0.76174(15) 0.85002(15) 0.20270(10) 0.0490(3) Uani 1 1 d . . . . .
H29A H 0.670045 0.850177 0.185921 0.059 Uiso 1 1 calc R U . . .
H29B H 0.825975 0.744567 0.220483 0.059 Uiso 1 1 calc R U . . .
C20 C 0.85801(15) 0.89825(17) 0.33380(10) 0.0526(3) Uani 1 1 d . . . . .
C7 C -0.27092(15) 0.75014(19) 0.93163(12) 0.0578(4) Uani 1 1 d . . . . .
H7A H -0.327862 0.831565 0.878491 0.069 Uiso 1 1 calc R U . . .
H7AB H -0.288542 0.786562 0.993480 0.069 Uiso 1 1 calc R U . . .
C26 C 0.84475(17) 0.94847(18) 0.10362(11) 0.0576(4) Uani 1 1 d . . . . .
H26A H 0.940242 0.942252 0.118338 0.069 Uiso 1 1 calc R U . . .
H26B H 0.866988 0.909255 0.042449 0.069 Uiso 1 1 calc R U . . .
C14 C 0.65104(16) 0.24212(17) 0.77920(12) 0.0604(4) Uani 1 1 d . . . . .
H14A H 0.668536 0.160939 0.748775 0.091 Uiso 1 1 calc R U . . .
H14B H 0.586473 0.223441 0.849066 0.091 Uiso 1 1 calc R U . . .
H14C H 0.746190 0.245188 0.786738 0.091 Uiso 1 1 calc R U . . .
C22 C 0.70422(16) 1.17777(16) 0.17090(12) 0.0576(4) Uani 1 1 d . . . . .
H22A H 0.636885 1.281616 0.151995 0.069 Uiso 1 1 calc R U . . .
H22B H 0.794132 1.182912 0.186857 0.069 Uiso 1 1 calc R U . . .
C9 C -0.29449(15) 0.54558(17) 0.87414(12) 0.0584(4) Uani 1 1 d . . . . .
H9A H -0.351128 0.620925 0.818687 0.070 Uiso 1 1 calc R U . . .
H9AB H -0.328066 0.453635 0.899214 0.070 Uiso 1 1 calc R U . . .
C27 C 0.74930(18) 1.11406(19) 0.07583(12) 0.0648(4) Uani 1 1 d . . . . .
H27A H 0.806039 1.175544 0.015192 0.078 Uiso 1 1 calc R U . . .
H27B H 0.658612 1.121226 0.053941 0.078 Uiso 1 1 calc R U . . .
C8 C -0.32643(16) 0.60924(19) 0.96726(12) 0.0629(4) Uani 1 1 d . . . . .
H8A H -0.276197 0.531068 1.025133 0.075 Uiso 1 1 calc R U . . .
H8AB H -0.434776 0.636428 0.995081 0.075 Uiso 1 1 calc R U . . .
C4 C -0.18384(17) 0.8564(2) 0.62355(12) 0.0673(4) Uani 1 1 d . . . . .
H4 H -0.226204 0.931032 0.565355 0.081 Uiso 1 1 calc R U . . .
C21 C 0.96643(18) 0.8929(2) 0.36020(14) 0.0760(5) Uani 1 1 d . . . . .
H21 H 1.052386 0.888626 0.381134 0.091 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
O001 C18 1.3434(16) . ?
O001 H001 0.8200 . ?
N002 C11 1.2563(16) . ?
N002 C5 1.4724(18) . ?
N003 C19 1.2650(17) . ?
N003 C23 1.4799(15) . ?
C18 C12 1.3973(16) . ?
C18 C17 1.4045(19) . ?
C5 C3 1.4691(19) . ?
C5 C6 1.531(2) . ?
C5 C10 1.536(2) . ?
C12 C13 1.3834(18) . ?
C12 C11 1.4683(19) . ?
C13 C15 1.3840(19) . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C17 C16 1.3883(19) . ?
C17 C19 1.4530(17) . ?
C15 C16 1.3862(18) . ?
C15 C14 1.497(2) . ?
C23 C20 1.469(2) . ?
C23 C29 1.532(2) . ?
C23 C28 1.522(2) . ?
C19 H19 0.9300 . ?
C6 C7 1.523(2) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C3 C4 1.1675(19) . ?
C16 H16 0.9300 . ?
C10 C9 1.517(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C28 C22 1.521(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C26 1.5272(19) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C20 C21 1.173(2) . ?
C7 C8 1.513(2) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C26 C27 1.507(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 C27 1.510(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C9 C8 1.504(2) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C4 H4 0.9300 . ?
C21 H21 0.9300 . ?

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
C18 O001 H001 109.5 . . ?
C11 N002 C5 121.59(10) . . ?
C19 N003 C23 121.31(11) . . ?
O001 C18 C12 119.43(11) . . ?
O001 C18 C17 120.93(10) . . ?
C12 C18 C17 119.63(11) . . ?
N002 C5 C3 113.78(10) . . ?
N002 C5 C6 107.09(9) . . ?
C3 C5 C6 109.80(12) . . ?
N002 C5 C10 106.71(11) . . ?
C3 C5 C10 109.79(11) . . ?
C6 C5 C10 109.55(10) . . ?
C18 C12 C13 118.87(11) . . ?
C18 C12 C11 120.69(11) . . ?
C13 C12 C11 120.44(10) . . ?
C15 C13 C12 122.96(10) . . ?
C15 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
N002 C11 C12 120.91(11) . . ?
N002 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C16 C17 C18 118.99(10) . . ?
C16 C17 C19 120.03(11) . . ?
C18 C17 C19 120.94(11) . . ?
C16 C15 C13 117.07(11) . . ?
C16 C15 C14 121.99(12) . . ?
C13 C15 C14 120.93(11) . . ?
C20 C23 N003 111.74(11) . . ?
C20 C23 C29 110.35(11) . . ?
N003 C23 C29 108.19(11) . . ?
C20 C23 C28 109.80(12) . . ?
N003 C23 C28 107.30(10) . . ?
C29 C23 C28 109.37(12) . . ?
N003 C19 C17 122.12(12) . . ?
N003 C19 H19 118.9 . . ?
C17 C19 H19 118.9 . . ?
C7 C6 C5 112.52(10) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6AB 109.1 . . ?
C5 C6 H6AB 109.1 . . ?
H6A C6 H6AB 107.8 . . ?
C4 C3 C5 179.58(16) . . ?
C15 C16 C17 122.37(12) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C9 C10 C5 112.25(11) . . ?
C9 C10 H10A 109.1 . . ?
C5 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C5 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C22 C28 C23 112.08(11) . . ?
C22 C28 H28A 109.2 . . ?
C23 C28 H28A 109.2 . . ?
C22 C28 H28B 109.2 . . ?
C23 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C23 C29 C26 111.31(12) . . ?
C23 C29 H29A 109.4 . . ?
C26 C29 H29A 109.4 . . ?
C23 C29 H29B 109.4 . . ?
C26 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C21 C20 C23 177.95(17) . . ?
C6 C7 C8 111.12(13) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7AB 109.4 . . ?
C8 C7 H7AB 109.4 . . ?
H7A C7 H7AB 108.0 . . ?
C27 C26 C29 110.59(12) . . ?
C27 C26 H26A 109.5 . . ?
C29 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C29 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C27 C22 C28 111.56(13) . . ?
C27 C22 H22A 109.3 . . ?
C28 C22 H22A 109.3 . . ?
C27 C22 H22B 109.3 . . ?
C28 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C8 C9 C10 111.09(12) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9AB 109.4 . . ?
C10 C9 H9AB 109.4 . . ?
H9A C9 H9AB 108.0 . . ?
C22 C27 C26 111.53(13) . . ?
C22 C27 H27A 109.3 . . ?
C26 C27 H27A 109.3 . . ?
C22 C27 H27B 109.3 . . ?
C26 C27 H27B 109.3 . . ?
H27A C27 H27B 108.0 . . ?
C9 C8 C7 110.77(12) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8AB 109.5 . . ?
C7 C8 H8AB 109.5 . . ?
H8A C8 H8AB 108.1 . . ?
C3 C4 H4 180.0 . . ?
C20 C21 H21 180.0 . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
