# 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 2019

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1850077'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION, CSIR-NIIST
India
;
_audit_update_record             
;
2018-06-18 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 N2 O2'
_chemical_formula_weight         376.40

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   10.877(3)
_cell_length_b                   8.6204(16)
_cell_length_c                   19.810(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.554(8)
_cell_angle_gamma                90.00
_cell_volume                     1826.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3083
_cell_measurement_theta_min      5.164
_cell_measurement_theta_max      46.034

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14929
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4532
_reflns_number_gt                2628
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0841P)²+0.1561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4532
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1791
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.07888(16) 1.25207(19) 0.17366(8) 0.0456(4) Uani 1 1 d . . .
O2 O 1.20979(14) 0.9390(2) 0.41593(8) 0.0464(4) Uani 1 1 d . . .
N1 N 0.73783(18) 0.7867(2) 0.43986(9) 0.0408(5) Uani 1 1 d . . .
N2 N 0.67191(17) 0.8296(2) 0.37732(9) 0.0408(5) Uani 1 1 d . . .
C1 C 0.5437(3) 0.6021(4) 0.58483(14) 0.0674(9) Uani 1 1 d . . .
H1 H 0.5003 0.5618 0.6172 0.081 Uiso 1 1 calc R . .
C2 C 0.4948(3) 0.7248(4) 0.54397(13) 0.0610(7) Uani 1 1 d . . .
H7 H 0.4178 0.7660 0.5485 0.073 Uiso 1 1 calc R . .
C3 C 0.5592(2) 0.7874(3) 0.49623(12) 0.0492(6) Uani 1 1 d . . .
H8 H 0.5262 0.8708 0.4691 0.059 Uiso 1 1 calc R . .
C4 C 0.6724(2) 0.7244(3) 0.48957(11) 0.0416(6) Uani 1 1 d . . .
C5 C 0.8624(2) 0.8156(2) 0.44380(10) 0.0369(5) Uani 1 1 d . . .
C6 C 0.87725(19) 0.8832(2) 0.38063(10) 0.0339(5) Uani 1 1 d . . .
C7 C 0.99901(19) 0.9286(2) 0.37291(10) 0.0345(5) Uani 1 1 d . . .
C8 C 1.05818(19) 1.0152(2) 0.32502(10) 0.0333(5) Uani 1 1 d . . .
C9 C 1.01885(19) 1.0976(2) 0.26364(10) 0.0339(5) Uani 1 1 d . . .
H4 H 0.9347 1.1021 0.2436 0.041 Uiso 1 1 calc R . .
C10 C 1.1075(2) 1.1712(2) 0.23392(11) 0.0357(5) Uani 1 1 d . . .
C11 C 1.2347(2) 1.1675(3) 0.26402(12) 0.0461(6) Uani 1 1 d . . .
H2 H 1.2926 1.2187 0.2428 0.055 Uiso 1 1 calc R . .
C12 C 1.2748(2) 1.0892(3) 0.32439(12) 0.0475(6) Uani 1 1 d . . .
H16 H 1.3589 1.0855 0.3446 0.057 Uiso 1 1 calc R . .
C13 C 1.1858(2) 1.0171(3) 0.35352(11) 0.0397(5) Uani 1 1 d . . .
C14 C 1.0954(2) 0.8907(3) 0.42703(11) 0.0400(5) Uani 1 1 d . . .
C15 C 0.7532(2) 0.8862(2) 0.34126(10) 0.0353(5) Uani 1 1 d . . .
C16 C 0.6560(3) 0.5398(4) 0.57776(14) 0.0647(8) Uani 1 1 d . . .
H6 H 0.6890 0.4571 0.6054 0.078 Uiso 1 1 calc R . .
C17 C 0.7208(3) 0.5992(3) 0.52964(13) 0.0527(7) Uani 1 1 d . . .
H5 H 0.7965 0.5553 0.5242 0.063 Uiso 1 1 calc R . .
C18 C 0.9624(2) 0.7875(3) 0.49896(11) 0.0429(6) Uani 1 1 d . . .
H10 H 0.9484 0.7464 0.5403 0.052 Uiso 1 1 calc R . .
C19 C 1.0800(2) 0.8229(3) 0.48921(11) 0.0451(6) Uani 1 1 d . . .
H9 H 1.1489 0.8024 0.5233 0.054 Uiso 1 1 calc R . .
C20 C 0.70543(19) 0.9262(2) 0.26900(10) 0.0337(5) Uani 1 1 d . . .
C21 C 0.7695(2) 0.8815(3) 0.21770(11) 0.0430(6) Uani 1 1 d . . .
H15 H 0.8468 0.8327 0.2291 0.052 Uiso 1 1 calc R . .
C22 C 0.7182(3) 0.9095(3) 0.14951(12) 0.0558(7) Uani 1 1 d . . .
H14 H 0.7620 0.8814 0.1152 0.067 Uiso 1 1 calc R . .
C23 C 0.6036(3) 0.9783(3) 0.13236(13) 0.0576(7) Uani 1 1 d . . .
H13 H 0.5692 0.9956 0.0864 0.069 Uiso 1 1 calc R . .
C24 C 0.5393(3) 1.0218(3) 0.18250(13) 0.0547(7) Uani 1 1 d . . .
H12 H 0.4612 1.0684 0.1706 0.066 Uiso 1 1 calc R . .
C25 C 0.5900(2) 0.9968(3) 0.25060(12) 0.0448(6) Uani 1 1 d . . .
H11 H 0.5463 1.0277 0.2845 0.054 Uiso 1 1 calc R . .
H3 H 0.987(3) 1.263(3) 0.1615(13) 0.067 Uiso 1 1 d . . .


_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 C10 1.368(3) . ?
O1 H3 0.99(3) . ?
O2 C14 1.367(3) . ?
O2 C13 1.390(3) . ?
N1 N2 1.364(2) . ?
N1 C5 1.366(3) . ?
N1 C4 1.422(3) . ?
N2 C15 1.327(3) . ?
C1 C16 1.364(4) . ?
C1 C2 1.378(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(3) . ?
C2 H7 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H8 0.9300 . ?
C4 C17 1.385(3) . ?
C5 C18 1.414(3) . ?
C5 C6 1.416(3) . ?
C6 C7 1.416(3) . ?
C6 C15 1.430(3) . ?
C7 C14 1.394(3) . ?
C7 C8 1.447(3) . ?
C8 C13 1.399(3) . ?
C8 C9 1.405(3) . ?
C9 C10 1.373(3) . ?
C9 H4 0.9300 . ?
C10 C11 1.403(3) . ?
C11 C12 1.373(3) . ?
C11 H2 0.9300 . ?
C12 C13 1.364(3) . ?
C12 H16 0.9300 . ?
C14 C19 1.401(3) . ?
C15 C20 1.471(3) . ?
C16 C17 1.384(4) . ?
C16 H6 0.9300 . ?
C17 H5 0.9300 . ?
C18 C19 1.362(3) . ?
C18 H10 0.9300 . ?
C19 H9 0.9300 . ?
C20 C25 1.383(3) . ?
C20 C21 1.388(3) . ?
C21 C22 1.385(3) . ?
C21 H15 0.9300 . ?
C22 C23 1.366(4) . ?
C22 H14 0.9300 . ?
C23 C24 1.368(4) . ?
C23 H13 0.9300 . ?
C24 C25 1.378(3) . ?
C24 H12 0.9300 . ?
C25 H11 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
C10 O1 H3 108.5(16) . . ?
C14 O2 C13 105.20(16) . . ?
N2 N1 C5 110.70(18) . . ?
N2 N1 C4 119.02(19) . . ?
C5 N1 C4 130.28(18) . . ?
C15 N2 N1 107.31(18) . . ?
C16 C1 C2 119.9(3) . . ?
C16 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H7 119.6 . . ?
C3 C2 H7 119.6 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H8 120.5 . . ?
C2 C3 H8 120.5 . . ?
C3 C4 C17 120.4(2) . . ?
C3 C4 N1 119.2(2) . . ?
C17 C4 N1 120.3(2) . . ?
N1 C5 C18 128.8(2) . . ?
N1 C5 C6 107.27(17) . . ?
C18 C5 C6 123.9(2) . . ?
C5 C6 C7 117.99(18) . . ?
C5 C6 C15 103.91(19) . . ?
C7 C6 C15 138.1(2) . . ?
C14 C7 C6 116.0(2) . . ?
C14 C7 C8 105.23(19) . . ?
C6 C7 C8 138.62(19) . . ?
C13 C8 C9 117.7(2) . . ?
C13 C8 C7 105.60(18) . . ?
C9 C8 C7 136.57(19) . . ?
C10 C9 C8 118.56(19) . . ?
C10 C9 H4 120.7 . . ?
C8 C9 H4 120.7 . . ?
O1 C10 C9 122.98(19) . . ?
O1 C10 C11 115.5(2) . . ?
C9 C10 C11 121.5(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H2 119.6 . . ?
C10 C11 H2 119.6 . . ?
C13 C12 C11 117.1(2) . . ?
C13 C12 H16 121.4 . . ?
C11 C12 H16 121.4 . . ?
C12 C13 O2 124.4(2) . . ?
C12 C13 C8 124.3(2) . . ?
O2 C13 C8 111.35(19) . . ?
O2 C14 C7 112.5(2) . . ?
O2 C14 C19 121.85(19) . . ?
C7 C14 C19 125.4(2) . . ?
N2 C15 C6 110.79(18) . . ?
N2 C15 C20 117.32(18) . . ?
C6 C15 C20 131.6(2) . . ?
C1 C16 C17 120.2(3) . . ?
C1 C16 H6 119.9 . . ?
C17 C16 H6 119.9 . . ?
C16 C17 C4 119.7(3) . . ?
C16 C17 H5 120.2 . . ?
C4 C17 H5 120.2 . . ?
C19 C18 C5 117.5(2) . . ?
C19 C18 H10 121.3 . . ?
C5 C18 H10 121.3 . . ?
C18 C19 C14 119.0(2) . . ?
C18 C19 H9 120.5 . . ?
C14 C19 H9 120.5 . . ?
C25 C20 C21 118.9(2) . . ?
C25 C20 C15 120.1(2) . . ?
C21 C20 C15 120.8(2) . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H15 120.0 . . ?
C20 C21 H15 120.0 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H14 119.8 . . ?
C21 C22 H14 119.8 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H13 119.9 . . ?
C24 C23 H13 119.9 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 H12 119.9 . . ?
C25 C24 H12 119.9 . . ?
C24 C25 C20 120.5(2) . . ?
C24 C25 H11 119.7 . . ?
C20 C25 H11 119.7 . . ?

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
C5 N1 N2 C15 -0.2(3) . . . . ?
C4 N1 N2 C15 178.79(19) . . . . ?
C16 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C17 0.6(4) . . . . ?
C2 C3 C4 N1 179.0(2) . . . . ?
N2 N1 C4 C3 -39.6(3) . . . . ?
C5 N1 C4 C3 139.2(2) . . . . ?
N2 N1 C4 C17 138.8(2) . . . . ?
C5 N1 C4 C17 -42.4(3) . . . . ?
N2 N1 C5 C18 -179.5(2) . . . . ?
C4 N1 C5 C18 1.7(4) . . . . ?
N2 N1 C5 C6 1.0(2) . . . . ?
C4 N1 C5 C6 -177.9(2) . . . . ?
N1 C5 C6 C7 178.05(18) . . . . ?
C18 C5 C6 C7 -1.5(3) . . . . ?
N1 C5 C6 C15 -1.3(2) . . . . ?
C18 C5 C6 C15 179.1(2) . . . . ?
C5 C6 C7 C14 4.9(3) . . . . ?
C15 C6 C7 C14 -176.0(2) . . . . ?
C5 C6 C7 C8 -170.4(2) . . . . ?
C15 C6 C7 C8 8.7(5) . . . . ?
C14 C7 C8 C13 2.0(2) . . . . ?
C6 C7 C8 C13 177.6(2) . . . . ?
C14 C7 C8 C9 -174.0(2) . . . . ?
C6 C7 C8 C9 1.6(5) . . . . ?
C13 C8 C9 C10 1.9(3) . . . . ?
C7 C8 C9 C10 177.6(2) . . . . ?
C8 C9 C10 O1 178.88(19) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
O1 C10 C11 C12 -179.6(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 O2 -177.0(2) . . . . ?
C11 C12 C13 C8 1.6(4) . . . . ?
C14 O2 C13 C12 177.5(2) . . . . ?
C14 O2 C13 C8 -1.2(2) . . . . ?
C9 C8 C13 C12 -2.3(3) . . . . ?
C7 C8 C13 C12 -179.2(2) . . . . ?
C9 C8 C13 O2 176.42(18) . . . . ?
C7 C8 C13 O2 -0.5(2) . . . . ?
C13 O2 C14 C7 2.6(2) . . . . ?
C13 O2 C14 C19 -172.4(2) . . . . ?
C6 C7 C14 O2 -179.68(18) . . . . ?
C8 C7 C14 O2 -2.9(2) . . . . ?
C6 C7 C14 C19 -4.9(3) . . . . ?
C8 C7 C14 C19 171.9(2) . . . . ?
N1 N2 C15 C6 -0.7(2) . . . . ?
N1 N2 C15 C20 174.07(18) . . . . ?
C5 C6 C15 N2 1.2(2) . . . . ?
C7 C6 C15 N2 -177.9(2) . . . . ?
C5 C6 C15 C20 -172.5(2) . . . . ?
C7 C6 C15 C20 8.3(4) . . . . ?
C2 C1 C16 C17 -0.1(4) . . . . ?
C1 C16 C17 C4 1.3(4) . . . . ?
C3 C4 C17 C16 -1.5(4) . . . . ?
N1 C4 C17 C16 -179.9(2) . . . . ?
N1 C5 C18 C19 178.1(2) . . . . ?
C6 C5 C18 C19 -2.4(3) . . . . ?
C5 C18 C19 C14 2.7(3) . . . . ?
O2 C14 C19 C18 175.3(2) . . . . ?
C7 C14 C19 C18 1.0(4) . . . . ?
N2 C15 C20 C25 40.1(3) . . . . ?
C6 C15 C20 C25 -146.5(2) . . . . ?
N2 C15 C20 C21 -134.0(2) . . . . ?
C6 C15 C20 C21 39.4(3) . . . . ?
C25 C20 C21 C22 0.8(3) . . . . ?
C15 C20 C21 C22 174.9(2) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
C21 C22 C23 C24 0.8(4) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C23 C24 C25 C20 -0.7(4) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
C15 C20 C25 C24 -174.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.079
