# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_SRM54_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2278567'
loop_
_audit_author_name
_audit_author_address
'Tapas Ghatak'
;Vellore Institute of Technology
India
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H28 N4 O'
_chemical_formula_sum            'C25 H28 N4 O'
_chemical_formula_weight         400.51

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      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                   8.0389(17)
_cell_length_b                   31.902(7)
_cell_length_c                   9.109(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.917(6)
_cell_angle_gamma                90
_cell_volume                     2196.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9998
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      21.69

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST  diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45071
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.699
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3857
_reflns_number_gt                2814
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0470P)²+0.7257P] 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         3857
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.43825(18) 0.25260(4) 0.39108(16) 0.0579(4) Uani 1 1 d . . . . .
N1 N 0.63748(19) 0.22454(4) 0.61134(16) 0.0405(4) Uani 1 1 d . . . . .
H1 H 0.699964 0.230621 0.706098 0.049 Uiso 1 1 calc R U . . .
N2 N 0.58890(19) 0.29494(4) 0.59766(17) 0.0416(4) Uani 1 1 d . . . . .
N3 N 0.72408(19) 0.33168(4) 0.44071(16) 0.0399(4) Uani 1 1 d . . . . .
N4 N 0.58025(19) 0.36650(4) 0.59384(17) 0.0413(4) Uani 1 1 d . . . . .
C1 C 0.6392(2) 0.18217(5) 0.56867(19) 0.0367(4) Uani 1 1 d . . . . .
C2 C 0.7627(2) 0.15628(6) 0.6726(2) 0.0476(5) Uani 1 1 d . . . . .
H2 H 0.837185 0.167169 0.766770 0.057 Uiso 1 1 calc R U . . .
C3 C 0.7765(3) 0.11466(6) 0.6382(2) 0.0536(5) Uani 1 1 d . . . . .
H3 H 0.860503 0.097966 0.709803 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6682(3) 0.09709(6) 0.4997(2) 0.0513(5) Uani 1 1 d . . . . .
C5 C 0.5460(3) 0.12309(6) 0.3981(2) 0.0546(5) Uani 1 1 d . . . . .
H5 H 0.472105 0.112072 0.303990 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5283(2) 0.16491(6) 0.4299(2) 0.0482(5) Uani 1 1 d . . . . .
H6 H 0.442695 0.181368 0.358792 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5492(2) 0.25721(5) 0.5214(2) 0.0397(4) Uani 1 1 d . . . . .
C8 C 0.6293(2) 0.32932(5) 0.54204(19) 0.0361(4) Uani 1 1 d . . . . .
C9 C 0.7495(2) 0.37067(6) 0.3764(2) 0.0440(5) Uani 1 1 d . . . . .
C10 C 0.7284(2) 0.40744(6) 0.4541(2) 0.0454(5) Uani 1 1 d . . . . .
C11 C 0.6554(2) 0.40519(5) 0.5741(2) 0.0446(5) Uani 1 1 d . . . . .
C12 C 0.6837(4) 0.05150(7) 0.4610(3) 0.0826(8) Uani 1 1 d . . . . .
H12A H 0.643122 0.047991 0.349657 0.124 Uiso 1 1 calc R U . . .
H12B H 0.612728 0.034703 0.504280 0.124 Uiso 1 1 calc R U . . .
H12C H 0.805071 0.042846 0.504356 0.124 Uiso 1 1 calc R U . . .
C13 C 0.8292(3) 0.29429(6) 0.4244(3) 0.0521(5) Uani 1 1 d . . . . .
H13 H 0.819093 0.273851 0.501233 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7549(4) 0.27245(8) 0.2653(3) 0.0881(9) Uani 1 1 d . . . . .
H14A H 0.795488 0.243945 0.274953 0.132 Uiso 1 1 calc R U . . .
H14B H 0.794847 0.286862 0.190931 0.132 Uiso 1 1 calc R U . . .
H14C H 0.628002 0.272883 0.230534 0.132 Uiso 1 1 calc R U . . .
C15 C 0.8026(3) 0.37358(7) 0.2483(2) 0.0617(6) Uani 1 1 d . . . . .
H15 H 0.809543 0.349611 0.192492 0.074 Uiso 1 1 calc R U . . .
C16 C 0.8463(3) 0.41270(9) 0.2022(3) 0.0806(8) Uani 1 1 d . . . . .
H16 H 0.880595 0.414389 0.114630 0.097 Uiso 1 1 calc R U . . .
C17 C 0.8398(3) 0.44806(9) 0.2815(4) 0.0815(8) Uani 1 1 d . . . . .
H17 H 0.874179 0.473445 0.250525 0.098 Uiso 1 1 calc R U . . .
C18 C 0.7811(3) 0.44683(6) 0.4113(3) 0.0640(6) Uani 1 1 d . . . . .
C19 C 0.6534(3) 0.44042(6) 0.6618(3) 0.0629(6) Uani 1 1 d . . . . .
H19 H 0.613511 0.438789 0.746209 0.076 Uiso 1 1 calc R U . . .
C20 C 0.7717(3) 0.48224(7) 0.4991(4) 0.0820(8) Uani 1 1 d . . . . .
H20 H 0.806195 0.508238 0.473286 0.098 Uiso 1 1 calc R U . . .
C21 C 0.7128(3) 0.47896(7) 0.6211(4) 0.0815(8) Uani 1 1 d . . . . .
H21 H 0.711287 0.502711 0.679898 0.098 Uiso 1 1 calc R U . . .
C22 C 0.4386(3) 0.36362(6) 0.6655(2) 0.0496(5) Uani 1 1 d . . . . .
H22 H 0.379707 0.336689 0.630943 0.060 Uiso 1 1 calc R U . . .
C23 C 0.2955(3) 0.39700(7) 0.6021(3) 0.0655(6) Uani 1 1 d . . . . .
H23A H 0.193430 0.389690 0.628727 0.098 Uiso 1 1 calc R U . . .
H23B H 0.263201 0.398572 0.490643 0.098 Uiso 1 1 calc R U . . .
H23C H 0.339964 0.423694 0.647219 0.098 Uiso 1 1 calc R U . . .
C24 C 1.0253(3) 0.30427(7) 0.4706(3) 0.0627(6) Uani 1 1 d . . . . .
H24A H 1.089741 0.278979 0.470034 0.094 Uiso 1 1 calc R U . . .
H24B H 1.066349 0.316281 0.573343 0.094 Uiso 1 1 calc R U . . .
H24C H 1.043485 0.323860 0.397487 0.094 Uiso 1 1 calc R U . . .
C25 C 0.5138(4) 0.36116(9) 0.8428(3) 0.0790(7) Uani 1 1 d . . . . .
H25A H 0.420548 0.354744 0.882645 0.118 Uiso 1 1 calc R U . . .
H25B H 0.566117 0.387598 0.884089 0.118 Uiso 1 1 calc R U . . .
H25C H 0.602278 0.339600 0.873493 0.118 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 C7 1.227(2) . ?
N1 C7 1.366(2) . ?
N1 C1 1.408(2) . ?
N2 C8 1.295(2) . ?
N2 C7 1.372(2) . ?
N3 C8 1.385(2) . ?
N3 C9 1.419(2) . ?
N3 C13 1.498(2) . ?
N4 C8 1.383(2) . ?
N4 C11 1.412(2) . ?
N4 C22 1.496(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.388(2) . ?
C2 C3 1.377(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.375(3) . ?
C4 C12 1.512(3) . ?
C5 C6 1.383(3) . ?
C9 C15 1.376(3) . ?
C9 C10 1.410(3) . ?
C10 C11 1.408(3) . ?
C10 C18 1.422(3) . ?
C11 C19 1.382(3) . ?
C13 C24 1.520(3) . ?
C13 C14 1.534(3) . ?
C15 C16 1.399(3) . ?
C16 C17 1.350(4) . ?
C17 C18 1.415(4) . ?
C18 C20 1.401(4) . ?
C19 C21 1.413(3) . ?
C20 C21 1.352(4) . ?
C22 C25 1.521(3) . ?
C22 C23 1.529(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
C7 N1 C1 128.24(15) . . ?
C8 N2 C7 126.23(15) . . ?
C8 N3 C9 120.79(14) . . ?
C8 N3 C13 118.68(14) . . ?
C9 N3 C13 119.45(15) . . ?
C8 N4 C11 121.48(15) . . ?
C8 N4 C22 116.36(14) . . ?
C11 N4 C22 122.11(14) . . ?
C2 C1 C6 118.27(16) . . ?
C2 C1 N1 117.08(15) . . ?
C6 C1 N1 124.64(16) . . ?
C3 C2 C1 120.87(17) . . ?
C2 C3 C4 121.57(18) . . ?
C5 C4 C3 116.90(17) . . ?
C5 C4 C12 121.34(19) . . ?
C3 C4 C12 121.8(2) . . ?
C4 C5 C6 122.84(18) . . ?
C5 C6 C1 119.54(17) . . ?
O1 C7 N1 123.18(16) . . ?
O1 C7 N2 124.19(16) . . ?
N1 C7 N2 112.46(15) . . ?
N2 C8 N4 117.04(15) . . ?
N2 C8 N3 125.10(15) . . ?
N4 C8 N3 117.80(15) . . ?
C15 C9 C10 119.67(18) . . ?
C15 C9 N3 122.61(18) . . ?
C10 C9 N3 117.62(17) . . ?
C11 C10 C9 120.03(16) . . ?
C11 C10 C18 119.99(19) . . ?
C9 C10 C18 120.0(2) . . ?
C19 C11 C10 119.82(18) . . ?
C19 C11 N4 123.18(19) . . ?
C10 C11 N4 116.95(16) . . ?
N3 C13 C24 111.87(16) . . ?
N3 C13 C14 113.84(19) . . ?
C24 C13 C14 112.94(18) . . ?
C9 C15 C16 119.8(2) . . ?
C17 C16 C15 121.7(2) . . ?
C16 C17 C18 120.6(2) . . ?
C20 C18 C17 123.6(2) . . ?
C20 C18 C10 118.5(2) . . ?
C17 C18 C10 118.0(2) . . ?
C11 C19 C21 119.0(2) . . ?
C21 C20 C18 120.6(2) . . ?
C20 C21 C19 121.8(2) . . ?
N4 C22 C25 112.35(17) . . ?
N4 C22 C23 112.27(16) . . ?
C25 C22 C23 114.37(18) . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.031



