# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_mo_surajit_ni_tbu_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2296145'
loop_
_audit_author_name
_audit_author_address
'Dr. Mamina Bhol'
;University of Hyderabad 
India
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_audit_creation_date             2023-09-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H22 N2 O2'
_chemical_formula_sum            'C27 H22 N2 O2'
_chemical_formula_weight         406.46
_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 0.0033 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.1135(6)
_cell_length_b                   10.4102(4)
_cell_length_c                   15.4220(5)
_cell_angle_alpha                90
_cell_angle_beta                 119.0150(10)
_cell_angle_gamma                90
_cell_volume                     2121.88(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9404
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.436
_cell_measurement_theta_min      2.471
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0835 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9625.
The λ/2 correction factor is Not present.
;

_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Niddle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51553
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         2.472
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4324
_reflns_number_total             5280
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.077
_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)+(0.0462P)²+0.5643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1278
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups
2. Others
 Fixed X: N2(0.57596) C20(0.55064)
 Fixed Y: N2(0.206129) C20(0.24378)
 Fixed Z: N2(0.51357) C20(0.58381)
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1A), N2(H2), C8(H8), C15(H15), C2(H2A), C3(H3), C18(H18), C4(H4),
 C17(H17), C16(H16), C25(H25), C20(H20), C27(H27), C26(H26)
3.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.29320(9) 0.45592(12) 0.37452(9) 0.0647(3) Uani 1 1 d . . . . .
N1 N 0.48083(9) 0.39874(13) 0.69810(9) 0.0529(3) Uani 1 1 d . . . . .
O1 O 0.27630(11) -0.01958(13) 0.47580(11) 0.0846(4) Uani 1 1 d . . . . .
C7 C 0.22420(9) 0.29858(13) 0.50274(9) 0.0414(3) Uani 1 1 d . . . . .
C14 C 0.33151(10) 0.33982(14) 0.69144(10) 0.0449(3) Uani 1 1 d . . . . .
C6 C 0.15782(10) 0.41198(14) 0.47472(9) 0.0419(3) Uani 1 1 d . . . . .
C12 C 0.41123(10) 0.37263(13) 0.59209(10) 0.0434(3) Uani 1 1 d . . . . .
H12 H 0.380166 0.455766 0.558712 0.052 Uiso 1 1 calc R . . . .
C13 C 0.42196(11) 0.40572(14) 0.74513(10) 0.0479(3) Uani 1 1 d . . . . .
C23 C 0.43512(11) 0.32271(14) 0.43774(12) 0.0503(3) Uani 1 1 d . . . . .
C11 C 0.32640(10) 0.28839(13) 0.59700(10) 0.0421(3) Uani 1 1 d . . . . .
C19 C 0.46443(11) 0.31507(14) 0.54124(11) 0.0496(3) Uani 1 1 d . . . . .
C5 C 0.05715(11) 0.40100(16) 0.40012(11) 0.0541(4) Uani 1 1 d . . . . .
H5 H 0.033147 0.320987 0.367399 0.065 Uiso 1 1 calc R . . . .
C1 C 0.18922(11) 0.53059(15) 0.52086(11) 0.0525(4) Uani 1 1 d . . . . .
H1A H 0.256795 0.540850 0.572807 0.063 Uiso 1 1 calc R . . . .
N2 N 0.575960 0.206129 0.513570 0.0827(5) Uani 1 1 d . . . . .
H2 H 0.629002 0.159347 0.524909 0.099 Uiso 1 1 calc R . . . .
C8 C 0.20272(11) 0.18946(15) 0.45009(11) 0.0536(4) Uani 1 1 d . . . . .
H8 H 0.146388 0.178710 0.385745 0.064 Uiso 1 1 calc R . . . .
C24 C 0.35741(12) 0.38489(15) 0.35572(12) 0.0531(4) Uani 1 1 d . . . . .
C9 C 0.27626(12) 0.09011(15) 0.50373(12) 0.0540(4) Uani 1 1 d . . . . .
C10 C 0.34897(11) 0.14304(14) 0.60364(11) 0.0519(4) Uani 1 1 d . . . . .
H10A H 0.419694 0.127629 0.618830 0.062 Uiso 1 1 calc R . . . .
H10B H 0.338292 0.102559 0.655920 0.062 Uiso 1 1 calc R . . . .
C15 C 0.26513(12) 0.32677(18) 0.72797(12) 0.0587(4) Uani 1 1 d . . . . .
H15 H 0.204575 0.278635 0.692447 0.070 Uiso 1 1 calc R . . . .
C2 C 0.12366(13) 0.63393(16) 0.49236(13) 0.0621(4) Uani 1 1 d . . . . .
H2A H 0.146912 0.714856 0.523735 0.075 Uiso 1 1 calc R . . . .
C3 C 0.02497(13) 0.62025(18) 0.41883(12) 0.0616(4) Uani 1 1 d . . . . .
H3 H -0.020068 0.691276 0.399933 0.074 Uiso 1 1 calc R . . . .
C18 C 0.44465(14) 0.46389(17) 0.83466(12) 0.0624(4) Uani 1 1 d . . . . .
H18 H 0.505978 0.510131 0.871424 0.075 Uiso 1 1 calc R . . . .
C22 C 0.50628(14) 0.25237(17) 0.42353(15) 0.0656(4) Uani 1 1 d . . . . .
C4 C -0.00802(12) 0.50455(19) 0.37319(12) 0.0629(4) Uani 1 1 d . . . . .
H4 H -0.076259 0.494998 0.322510 0.076 Uiso 1 1 calc R . . . .
C17 C 0.37576(15) 0.45273(19) 0.86880(12) 0.0703(5) Uani 1 1 d . . . . .
H17 H 0.389780 0.493124 0.929379 0.084 Uiso 1 1 calc R . . . .
C16 C 0.28768(14) 0.3848(2) 0.81740(13) 0.0693(5) Uani 1 1 d . . . . .
H16 H 0.241993 0.377397 0.842981 0.083 Uiso 1 1 calc R . . . .
C25 C 0.35103(15) 0.37221(18) 0.26370(13) 0.0679(5) Uani 1 1 d . . . . .
H25 H 0.297638 0.412907 0.207562 0.081 Uiso 1 1 calc R . . . .
C20 C 0.550640 0.243780 0.583810 0.0703(5) Uani 1 1 d . . . . .
H20 H 0.587885 0.223105 0.652317 0.084 Uiso 1 1 calc R . . . .
C27 C 0.50093(19) 0.2395(2) 0.33074(19) 0.0834(6) Uani 1 1 d . . . . .
H27 H 0.549527 0.190878 0.322453 0.100 Uiso 1 1 calc R . . . .
C26 C 0.4228(2) 0.2997(2) 0.25298(17) 0.0829(6) Uani 1 1 d . . . . .
H26 H 0.416983 0.292239 0.189010 0.099 Uiso 1 1 calc R . . . .
C28 C 0.21893(16) 0.5313(2) 0.29714(15) 0.0844(6) Uani 1 1 d . . . . .
H28A H 0.182396 0.582600 0.322865 0.127 Uiso 1 1 calc GR . . . .
H28B H 0.171239 0.474887 0.244144 0.127 Uiso 1 1 calc GR . . . .
H28C H 0.251680 0.588498 0.270788 0.127 Uiso 1 1 calc GR . . . .
H1 H 0.523(2) 0.466(3) 0.708(2) 0.127 Uiso 1 1 d R . . . .


_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
O2 C24 1.3584(19) . ?
O2 C28 1.414(2) . ?
N1 C12 1.4782(18) . ?
N1 C13 1.396(2) . ?
N1 H1 0.90(3) . ?
O1 C9 1.2206(19) . ?
C7 C6 1.4718(18) . ?
C7 C11 1.5271(17) . ?
C7 C8 1.341(2) . ?
C14 C13 1.388(2) . ?
C14 C11 1.5180(19) . ?
C14 C15 1.375(2) . ?
C6 C5 1.3977(19) . ?
C6 C1 1.389(2) . ?
C12 H12 1.0000 . ?
C12 C11 1.5852(19) . ?
C12 C19 1.4941(19) . ?
C13 C18 1.390(2) . ?
C23 C19 1.437(2) . ?
C23 C24 1.399(2) . ?
C23 C22 1.403(2) . ?
C11 C10 1.5436(19) . ?
C19 C20 1.3600(14) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.382(2) . ?
N2 H2 0.8800 . ?
N2 C22 1.360(2) . ?
N2 C20 1.36953(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.448(2) . ?
C24 C25 1.381(2) . ?
C9 C10 1.498(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.375(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.362(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.381(3) . ?
C22 C27 1.400(3) . ?
C4 H4 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.370(3) . ?
C16 H16 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.396(3) . ?
C20 H20 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.361(3) . ?
C26 H26 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
C24 O2 C28 118.59(14) . . ?
C12 N1 H1 112.9(18) . . ?
C13 N1 C12 107.06(11) . . ?
C13 N1 H1 116.6(18) . . ?
C6 C7 C11 124.46(12) . . ?
C8 C7 C6 124.83(12) . . ?
C8 C7 C11 110.70(12) . . ?
C13 C14 C11 108.89(12) . . ?
C15 C14 C13 120.50(14) . . ?
C15 C14 C11 130.58(14) . . ?
C5 C6 C7 119.41(13) . . ?
C1 C6 C7 123.22(12) . . ?
C1 C6 C5 117.35(13) . . ?
N1 C12 H12 108.3 . . ?
N1 C12 C11 101.95(11) . . ?
N1 C12 C19 112.27(11) . . ?
C11 C12 H12 108.3 . . ?
C19 C12 H12 108.3 . . ?
C19 C12 C11 117.19(12) . . ?
C14 C13 N1 110.84(12) . . ?
C14 C13 C18 120.34(15) . . ?
C18 C13 N1 128.79(14) . . ?
C24 C23 C19 134.53(14) . . ?
C24 C23 C22 118.10(15) . . ?
C22 C23 C19 107.33(15) . . ?
C7 C11 C12 112.59(11) . . ?
C7 C11 C10 102.72(11) . . ?
C14 C11 C7 116.50(11) . . ?
C14 C11 C12 100.65(10) . . ?
C14 C11 C10 112.05(12) . . ?
C10 C11 C12 112.80(11) . . ?
C23 C19 C12 127.33(13) . . ?
C20 C19 C12 126.79(12) . . ?
C20 C19 C23 105.87(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.10(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C2 C1 C6 121.00(14) . . ?
C2 C1 H1A 119.5 . . ?
C22 N2 H2 125.3 . . ?
C22 N2 C20 109.34(7) . . ?
C20 N2 H2 125.3 . . ?
C7 C8 H8 124.3 . . ?
C7 C8 C9 111.45(13) . . ?
C9 C8 H8 124.3 . . ?
O2 C24 C23 115.61(13) . . ?
O2 C24 C25 124.77(16) . . ?
C25 C24 C23 119.62(16) . . ?
O1 C9 C8 126.74(15) . . ?
O1 C9 C10 125.56(15) . . ?
C8 C9 C10 107.57(12) . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C9 C10 C11 105.32(12) . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.20(16) . . ?
C16 C15 H15 120.4 . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.36(16) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.78(15) . . ?
C4 C3 H3 120.1 . . ?
C13 C18 H18 120.9 . . ?
C17 C18 C13 118.28(16) . . ?
C17 C18 H18 120.9 . . ?
N2 C22 C23 107.32(14) . . ?
N2 C22 C27 129.91(17) . . ?
C27 C22 C23 122.8(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.40(15) . . ?
C3 C4 H4 119.8 . . ?
C18 C17 H17 119.2 . . ?
C16 C17 C18 121.58(16) . . ?
C16 C17 H17 119.2 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.05(16) . . ?
C17 C16 H16 120.0 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C19 C20 N2 110.13(6) . . ?
C19 C20 H20 124.9 . . ?
N2 C20 H20 124.9 . . ?
C22 C27 H27 121.6 . . ?
C26 C27 C22 116.86(18) . . ?
C26 C27 H27 121.6 . . ?
C25 C26 H26 118.8 . . ?
C27 C26 C25 122.46(18) . . ?
C27 C26 H26 118.8 . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
O2 C24 C25 C26 178.10(16) . . . . ?
N1 C12 C11 C7 153.61(11) . . . . ?
N1 C12 C11 C14 28.87(12) . . . . ?
N1 C12 C11 C10 -90.69(13) . . . . ?
N1 C12 C19 C23 -153.64(15) . . . . ?
N1 C12 C19 C20 26.77(19) . . . . ?
N1 C13 C18 C17 -176.85(16) . . . . ?
O1 C9 C10 C11 172.59(17) . . . . ?
C7 C6 C5 C4 178.65(14) . . . . ?
C7 C6 C1 C2 -179.44(14) . . . . ?
C7 C11 C10 C9 14.54(15) . . . . ?
C7 C8 C9 O1 179.03(18) . . . . ?
C7 C8 C9 C10 3.06(19) . . . . ?
C14 C13 C18 C17 0.8(2) . . . . ?
C14 C11 C10 C9 140.33(12) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C6 C7 C11 C14 42.58(18) . . . . ?
C6 C7 C11 C12 -72.96(16) . . . . ?
C6 C7 C11 C10 165.43(13) . . . . ?
C6 C7 C8 C9 -172.03(13) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C1 C2 C3 1.4(3) . . . . ?
C12 N1 C13 C14 23.15(16) . . . . ?
C12 N1 C13 C18 -158.98(15) . . . . ?
C12 C11 C10 C9 -106.93(13) . . . . ?
C12 C19 C20 N2 179.17(12) . . . . ?
C13 N1 C12 C11 -32.27(14) . . . . ?
C13 N1 C12 C19 -158.52(12) . . . . ?
C13 C14 C11 C7 -138.87(12) . . . . ?
C13 C14 C11 C12 -16.83(14) . . . . ?
C13 C14 C11 C10 103.28(14) . . . . ?
C13 C14 C15 C16 2.6(2) . . . . ?
C13 C18 C17 C16 1.0(3) . . . . ?
C23 C19 C20 N2 -0.50(12) . . . . ?
C23 C24 C25 C26 -1.2(2) . . . . ?
C23 C22 C27 C26 0.5(3) . . . . ?
C11 C7 C6 C5 -165.26(13) . . . . ?
C11 C7 C6 C1 12.9(2) . . . . ?
C11 C7 C8 C9 6.96(18) . . . . ?
C11 C14 C13 N1 -2.74(16) . . . . ?
C11 C14 C13 C18 179.18(13) . . . . ?
C11 C14 C15 C16 -179.67(15) . . . . ?
C11 C12 C19 C23 88.86(18) . . . . ?
C11 C12 C19 C20 -90.73(16) . . . . ?
C19 C12 C11 C7 -83.43(14) . . . . ?
C19 C12 C11 C14 151.83(12) . . . . ?
C19 C12 C11 C10 32.27(16) . . . . ?
C19 C23 C24 O2 0.3(3) . . . . ?
C19 C23 C24 C25 179.68(16) . . . . ?
C19 C23 C22 N2 -0.89(17) . . . . ?
C19 C23 C22 C27 -179.96(17) . . . . ?
C5 C6 C1 C2 -1.3(2) . . . . ?
C1 C6 C5 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
N2 C22 C27 C26 -178.34(16) . . . . ?
C8 C7 C6 C5 13.6(2) . . . . ?
C8 C7 C6 C1 -168.30(15) . . . . ?
C8 C7 C11 C14 -136.41(14) . . . . ?
C8 C7 C11 C12 108.05(14) . . . . ?
C8 C7 C11 C10 -13.56(16) . . . . ?
C8 C9 C10 C11 -11.39(17) . . . . ?
C24 C23 C19 C12 3.4(3) . . . . ?
C24 C23 C19 C20 -176.98(15) . . . . ?
C24 C23 C22 N2 177.36(12) . . . . ?
C24 C23 C22 C27 -1.7(3) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C15 C14 C13 N1 175.43(14) . . . . ?
C15 C14 C13 C18 -2.6(2) . . . . ?
C15 C14 C11 C7 43.2(2) . . . . ?
C15 C14 C11 C12 165.25(15) . . . . ?
C15 C14 C11 C10 -74.65(19) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C18 C17 C16 C15 -1.0(3) . . . . ?
C22 C23 C19 C12 -178.81(15) . . . . ?
C22 C23 C19 C20 0.85(16) . . . . ?
C22 C23 C24 O2 -177.35(14) . . . . ?
C22 C23 C24 C25 2.0(2) . . . . ?
C22 N2 C20 C19 -0.05(10) . . . . ?
C22 C27 C26 C25 0.4(3) . . . . ?
C20 N2 C22 C23 0.60(14) . . . . ?
C20 N2 C22 C27 179.58(17) . . . . ?
C28 O2 C24 C23 173.96(16) . . . . ?
C28 O2 C24 C25 -5.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2296148'
loop_
_audit_author_name
_audit_author_address
'DEBOJYOTI BAG'
;CSIR Indian Institute of Integrative Medicine
India
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_shelx               
;
PROBLEM: _diffrn_measured_fraction_theta_full valu_Low.0.954 Why? 
RESPONSE: The incomplete coverage of diffraction pattern and some data rejected as poor during integration and scaling.
;
# 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         ?
_chemical_formula_sum            'C27 H22 N2 O'
_chemical_formula_weight         390.46

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   37.641(3)
_cell_length_b                   7.1425(6)
_cell_length_c                   15.2538(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.978(3)
_cell_angle_gamma                90
_cell_volume                     4039.0(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9654
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.257
_cell_measurement_theta_min      2.744

_exptl_crystal_description       Rectangle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8507.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12385
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.712
_diffrn_reflns_theta_max         28.258
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             4339
_reflns_number_gt                2941
_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 2018/2 (Sheldrick, 2018)'
_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)+(0.0589P)²+0.9772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4339
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.33253(4) 0.76658(19) 0.44998(8) 0.0603(4) Uani 1 1 d . . . . .
N2 N 0.36187(5) 0.8946(2) 0.85454(10) 0.0491(4) Uani 1 1 d . . . . .
H2 H 0.3529(6) 1.000(3) 0.8776(15) 0.074 Uiso 1 1 d . U . . .
N1 N 0.31039(4) 0.3817(2) 0.75605(10) 0.0455(4) Uani 1 1 d . . . . .
H1 H 0.3117(5) 0.342(3) 0.8148(15) 0.068 Uiso 1 1 d . U . . .
C14 C 0.31262(4) 0.2807(2) 0.61459(11) 0.0361(4) Uani 1 1 d . . . . .
C11 C 0.33953(4) 0.4411(2) 0.63298(10) 0.0347(4) Uani 1 1 d . . . . .
C10 C 0.32300(5) 0.6226(2) 0.58881(11) 0.0403(4) Uani 1 1 d . . . . .
H10A H 0.296721 0.607843 0.568366 0.048 Uiso 1 1 calc R U . . .
H10B H 0.327122 0.728783 0.631098 0.048 Uiso 1 1 calc R U . . .
C12 C 0.34604(4) 0.4411(2) 0.73757(11) 0.0367(4) Uani 1 1 d . . . . .
H12 H 0.363653 0.339040 0.758546 0.044 Uiso 1 1 calc R U . . .
C7 C 0.37304(4) 0.4151(2) 0.59098(11) 0.0366(4) Uani 1 1 d . . . . .
C15 C 0.30205(5) 0.1755(3) 0.53880(12) 0.0439(4) Uani 1 1 d . . . . .
H15 H 0.313111 0.193555 0.487992 0.053 Uiso 1 1 calc R U . . .
C13 C 0.29623(5) 0.2557(2) 0.68888(11) 0.0398(4) Uani 1 1 d . . . . .
C19 C 0.35932(5) 0.6152(2) 0.78603(11) 0.0399(4) Uani 1 1 d . . . . .
C22 C 0.39641(5) 0.6570(2) 0.82152(11) 0.0393(4) Uani 1 1 d . . . . .
C21 C 0.39692(5) 0.8334(3) 0.86359(11) 0.0412(4) Uani 1 1 d . . . . .
C6 C 0.40157(5) 0.2768(2) 0.61953(11) 0.0394(4) Uani 1 1 d . . . . .
C20 C 0.33965(5) 0.7621(3) 0.80867(12) 0.0477(5) Uani 1 1 d . . . . .
H20 H 0.314122 0.771413 0.794655 0.057 Uiso 1 1 calc R U . . .
C9 C 0.34195(5) 0.6550(2) 0.51128(11) 0.0433(4) Uani 1 1 d . . . . .
C16 C 0.27505(5) 0.0427(3) 0.53769(14) 0.0521(5) Uani 1 1 d . . . . .
H16 H 0.267738 -0.031875 0.486161 0.062 Uiso 1 1 calc R U . . .
C18 C 0.26886(5) 0.1248(3) 0.68782(14) 0.0519(5) Uani 1 1 d . . . . .
H18 H 0.257368 0.108193 0.738033 0.062 Uiso 1 1 calc R U . . .
C1 C 0.39450(5) 0.0986(3) 0.64904(12) 0.0482(5) Uani 1 1 d . . . . .
H1A H 0.370428 0.063837 0.652565 0.058 Uiso 1 1 calc R U . . .
C8 C 0.37298(5) 0.5317(2) 0.52204(12) 0.0448(4) Uani 1 1 d . . . . .
H8 H 0.390895 0.533312 0.485171 0.054 Uiso 1 1 calc R U . . .
C23 C 0.42912(5) 0.5648(3) 0.82126(13) 0.0486(5) Uani 1 1 d . . . . .
H23 H 0.429663 0.446019 0.793512 0.058 Uiso 1 1 calc R U . . .
C26 C 0.42870(6) 0.9222(3) 0.90329(12) 0.0488(5) Uani 1 1 d . . . . .
C17 C 0.25882(5) 0.0191(3) 0.61136(15) 0.0556(5) Uani 1 1 d . . . . .
H17 H 0.240296 -0.071880 0.609640 0.067 Uiso 1 1 calc R U . . .
C5 C 0.43729(5) 0.3231(3) 0.61637(14) 0.0559(5) Uani 1 1 d . . . . .
H5 H 0.442827 0.443820 0.596289 0.067 Uiso 1 1 calc R U . . .
C25 C 0.45998(6) 0.8255(3) 0.90187(14) 0.0595(6) Uani 1 1 d . . . . .
H25 H 0.482210 0.879861 0.929029 0.071 Uiso 1 1 calc R U . . .
C2 C 0.42215(6) -0.0281(3) 0.67324(13) 0.0624(6) Uani 1 1 d . . . . .
H2A H 0.416899 -0.150184 0.692126 0.075 Uiso 1 1 calc R U . . .
C27 C 0.42784(6) 1.1147(3) 0.94217(15) 0.0649(6) Uani 1 1 d . . . . .
H27A H 0.452557 1.157094 0.963942 0.097 Uiso 1 1 calc R U . . .
H27B H 0.414374 1.111546 0.991668 0.097 Uiso 1 1 calc R U . . .
H27C H 0.416043 1.201117 0.896301 0.097 Uiso 1 1 calc R U . . .
C24 C 0.46044(6) 0.6490(3) 0.86181(14) 0.0598(6) Uani 1 1 d . . . . .
H24 H 0.482804 0.586741 0.862766 0.072 Uiso 1 1 calc R U . . .
C3 C 0.45706(6) 0.0208(4) 0.67023(14) 0.0698(7) Uani 1 1 d . . . . .
H3 H 0.475985 -0.066588 0.687698 0.084 Uiso 1 1 calc R U . . .
C4 C 0.46469(6) 0.1962(4) 0.64197(16) 0.0717(7) Uani 1 1 d . . . . .
H4 H 0.488934 0.230276 0.640034 0.086 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 C9 1.233(2) . ?
N2 C20 1.372(2) . ?
N2 C21 1.374(2) . ?
N1 C13 1.398(2) . ?
N1 C12 1.480(2) . ?
C14 C15 1.378(2) . ?
C14 C13 1.392(2) . ?
C14 C11 1.523(2) . ?
C11 C7 1.522(2) . ?
C11 C10 1.542(2) . ?
C11 C12 1.571(2) . ?
C10 C9 1.501(2) . ?
C12 C19 1.488(2) . ?
C7 C8 1.341(2) . ?
C7 C6 1.468(2) . ?
C15 C16 1.388(3) . ?
C13 C18 1.389(2) . ?
C19 C20 1.362(2) . ?
C19 C22 1.438(2) . ?
C22 C23 1.397(2) . ?
C22 C21 1.413(2) . ?
C21 C26 1.396(3) . ?
C6 C1 1.391(2) . ?
C6 C5 1.394(2) . ?
C9 C8 1.449(3) . ?
C16 C17 1.379(3) . ?
C18 C17 1.386(3) . ?
C1 C2 1.381(3) . ?
C23 C24 1.372(3) . ?
C26 C25 1.369(3) . ?
C26 C27 1.499(3) . ?
C5 C4 1.378(3) . ?
C25 C24 1.402(3) . ?
C2 C3 1.368(3) . ?
C3 C4 1.371(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
C20 N2 C21 108.78(15) . . ?
C13 N1 C12 106.73(13) . . ?
C15 C14 C13 120.57(16) . . ?
C15 C14 C11 130.60(15) . . ?
C13 C14 C11 108.71(14) . . ?
C7 C11 C14 113.83(13) . . ?
C7 C11 C10 102.70(13) . . ?
C14 C11 C10 110.31(13) . . ?
C7 C11 C12 115.63(13) . . ?
C14 C11 C12 99.71(12) . . ?
C10 C11 C12 115.08(13) . . ?
C9 C10 C11 105.24(13) . . ?
N1 C12 C19 112.48(14) . . ?
N1 C12 C11 101.91(13) . . ?
C19 C12 C11 118.94(14) . . ?
C8 C7 C6 123.52(16) . . ?
C8 C7 C11 111.43(15) . . ?
C6 C7 C11 125.03(14) . . ?
C14 C15 C16 119.14(17) . . ?
C18 C13 C14 120.60(17) . . ?
C18 C13 N1 129.02(16) . . ?
C14 C13 N1 110.33(15) . . ?
C20 C19 C22 106.24(16) . . ?
C20 C19 C12 128.21(17) . . ?
C22 C19 C12 125.51(15) . . ?
C23 C22 C21 118.63(16) . . ?
C23 C22 C19 134.40(17) . . ?
C21 C22 C19 106.97(16) . . ?
N2 C21 C26 129.41(18) . . ?
N2 C21 C22 107.50(16) . . ?
C26 C21 C22 123.07(18) . . ?
C1 C6 C5 117.91(17) . . ?
C1 C6 C7 122.72(16) . . ?
C5 C6 C7 119.37(16) . . ?
C19 C20 N2 110.51(17) . . ?
O1 C9 C8 126.77(17) . . ?
O1 C9 C10 125.70(17) . . ?
C8 C9 C10 107.53(15) . . ?
C17 C16 C15 120.03(19) . . ?
C17 C18 C13 118.03(18) . . ?
C2 C1 C6 120.58(19) . . ?
C7 C8 C9 110.97(16) . . ?
C24 C23 C22 118.76(18) . . ?
C25 C26 C21 116.00(18) . . ?
C25 C26 C27 123.14(19) . . ?
C21 C26 C27 120.8(2) . . ?
C16 C17 C18 121.62(18) . . ?
C4 C5 C6 120.9(2) . . ?
C26 C25 C24 122.43(19) . . ?
C3 C2 C1 120.5(2) . . ?
C23 C24 C25 121.1(2) . . ?
C2 C3 C4 119.9(2) . . ?
C3 C4 C5 120.2(2) . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037



