Crystal structure and Hirshfeld surface analysis of the chalcone derivative (2E)-3-[4-(di­phenyl­amino)phen­yl]-1-[4-(prop-1-yn-2-yl­oxy)phen­yl]prop-2-en-1-one

Madhan, S.; NizamMohideen, M.; Viswanathan, V.; Velmurugan, D.

doi:10.1107/S2056989024011721

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ISSN: 2056-9890

Volume 81| Part 1| January 2025| Pages 15-19

https://doi.org/10.1107/S2056989024011721

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Crystal structure and Hirshfeld surface analysis of the chalcone derivative (2E)-3-[4-(diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one

Sundarasamy Madhan,^a M. NizamMohideen,^a ^* Vijayan Viswanathan ^b and Devadasan Velmurugan ^c

^aDepartment of Physics, The New College, Chennai 600 014, University of Madras, Tamil Nadu, India, ^bCentre of Excellence in Structural Biology and Drug Discovery, Department of Biotechnology, SRM Institute of Science and Technology, Kattankulathur Campus, Chengalpattu, Tamil Nadu - 603203, India, and ^cDepartment of Biotechnology, SRM Institute of Science and Technology, Kattankulathur Campus, Chengalpattu, Tamil Nadu - 603203, India
^*Correspondence e-mail: mnizam.new@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 17 September 2024; accepted 2 December 2024; online 1 January 2025)

In the crystal structure of the title chalcone derivative, C₃₀H₂₃NO₂, the molecule adopts an s-cis conformation with respect to the C=O and C=C bonds. The triphenylamine moiety has a propeller-type shape, with dihedral angles between the mean planes of pairs of phenyl rings of 72.1 (6), 69.7 (1) and 65.6 (6)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains extending parallel to [010]. In addition, weak C—H⋯π interactions consolidate the crystal packing. One of the phenyl rings of the triphenylamine moiety is disordered over two sets of sites.

Keywords: crystal structure; chalcone; triphenylamine; hydrogen bonding; Hirshfeld surface analysis; disorder.

CCDC reference: 2406922

1. Chemical context

Chalcones are an important class of compounds, with the common structural entity being the central –CH=CH—C(=O)– bridge, in which the H atoms can be substituted. Chalcones provide a necessary configuration for NLO activity, with two planar rings connected through a conjugated double bond (NizamMohideen et al., 2007). They are also inherently chiral owing to the fact that the two phenyl rings are mutually twisted with respect to the linking backbone (Butcher et al., 2006 ). This helicity has also been shown to lead to NLO activity (Botek et al., 2004 ). The design of the chalcone system, e.g. in terms of donor—π⋯acceptor (D—π⋯A) interactions, plays a significant role in intramolecular charge-transfer transitions (ICT) where optical excitation leads to the movement of charge from the donor group to the acceptor group. In addition, the chalcone bridge consists of two different double bonds, C=C and C=O, which contribute to the conjugation of charge transfer, leading to interesting spectroscopic properties (de Toledo et al., 2018 ). The biological properties of chalcone derivatives such as anticancer (Bhat et al., 2005 ), antimalarial (Xue et al., 2004 ), anti-oxidant and antimicrobial (Yayli et al., 2006 ), antiplatelet (Zhao et al., 2005 ) as well as anti-inflammatory (Madan et al., 2000 ) activities have been studied extensively and are constantly developed further. Triphenylamine (TPA) derivatives, on the other hand, are important compounds used in numerous applications, e.g. in dye-sensitized solar cells (Lin et al., 2010 ).

In view of the application potentials mentioned above, we synthesized the title compound and report here its molecular and crystal structure and Hirshfeld surface analysis.

2. Structural commentary

In the molecular structure of the title compound, Fig. 1, the enone moiety (O1/C19–C21) has a maximum deviation from planarity of 0.0217 (18) Å at C21 and adopts ans-cis conformation with respect to the C21=O1 bond [1.2161 (17) Å] and the C19=C20 bond [1.3230 (18) Å]. The molecule is twisted about the C20—C21 bond with a C19—C20—C21—O1 torsion angle of 5.4 (2)°. A slight twist is also observed about the C21—C22 bond with an O1—C21—C22—C27 torsion angle of 179.55 (15)°. The twisted nature of this part of the molecule is expected because of the steric effects between the carbonyl group and the vicinal phenyl group (Kozlowski et al., 2007 ).

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

The (C1–C6) phenyl ring is disordered over two sets of siteswith a refined occupancy ratio of 0.55 (3):0.45 (3). In the triphenylamine group, the three phenyl rings form a propeller-type shape with dihedral angles of 72.1 (6)° between rings (C1–C6) and (C7–C12), of 65.6 (6)° between rings (C1—C6) and (C13–C18), and of 69.7 (1)° between rings (C7—C12) and (C13–C18). The enone moiety forms dihedral angles of 5.64 (10), 68.0 (5), 68.93 (10) and 4.18 (10)°, respectively, with the (C22–C27) phenyl ring and the (C1–C6), (C7–C12), and (C13–C18) phenyl rings of the triphenylamine group. The large variation of the dihedral angles between the enone moiety and the phenyl rings indicates that the possibility for electronic effects has decreased (Jung et al., 2008 ). The widening of the C20—C19—C16 angle to 127.70 (13)° and of the C19—C16—C17 angle to 122.83 (12)° can be ascribed to the short interatomic contact between atoms H20⋯H17 (2.22 Å). In addition, the strain induced by the short H27⋯H20 (2.10 Å) contact results in a slight opening of the C21—C22—C27 angle to 123.91 (12)°. Similar features have been observed in other comparable structures (Nizam Mohideen et al., 2007 ; Ravishankar et al., 2005 ).

3. Supramolecular features

In the crystal, the molecules are linked via weak C30—H30⋯O1 intermolecular interactions (Table 1) into chains extending parallel to [010] with a C(11) motif (Bernstein et al. 1995 ). The crystal packing also features C—H⋯π interactions [C28—H28A⋯Cg1ⁱ and C30—H30⋯Cg2ⁱⁱ, where Cg1 and Cg2 are the centres of gravity of the rings (C7–C12) and (C22—C27)]. Numerical details of the latter are compiled in Table 1, and a packing view is shown in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C30—H30⋯O1ⁱ	0.93	2.55	3.054 (2)	114
C28—H28A⋯Cg(C7–C12)ⁱⁱ	0.93	2.97	3.853 (2)	153
C30—H30⋯Cg(C22–C27)ⁱⁱⁱ	0.93	2.72	3.527 (2)	145
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 2
A view along the a axis of the title compound, showing the crystal packing. C—H⋯O hydrogen bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

4. Hirshfeld surface analysis

A recent article by Tiekink and collaborators (Tan et al., 2019 ) reviewed and described the utility of Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ) for analysis and quantification of intermolecular contacts in crystals. We also performed such calculations (surface mapped over d_norm and two-dimensional fingerprint plots) by using CrystalExplorer (Spackman et al., 2021 ). The Hirshfeld surface of the title compound mapped over d_norm is shown in Fig. 3, where the normalized contact distance, d_norm, is colour-mapped from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The red spots visible indicate the intermolecular contacts involved in hydrogen-bonding interactions, as discussed above. The two-dimensional fingerprint plots detailing the various interactions are displayed in Fig. 4a for all contacts. H⋯H intermolecular contacts predominate, followed by the C⋯H/H⋯C and O⋯H/H⋯O contacts corresponding to the different kinds of C—H⋯π and C—H⋯O bonds. This is manifested by the contributions of H⋯H contacts at 50.3% (Fig. 4b), H⋯C/C⋯H contacts at 36.7% (Fig. 4c), and O⋯H/H⋯O at 9.3% (Fig. 4d). Other contacts, viz. C⋯C at 2.4% (Fig. 4e), O⋯C/C⋯O at 0.9% (Fig. 4f) and N⋯H/H⋯N contacts at 0.3% (Fig. 4g) play a minor role.

Figure 3
The Hirshfeld surfaces of the title compound mapped over d_norm.

Figure 4
(a) The full two-dimensional fingerprint plot for the title compound, and fingerprint plots delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O, (e) C⋯C (f) O⋯C/C⋯O and (g) N⋯H/H⋯N contacts.

5. Database survey

A survey of Cambridge Structural Database (CSD, Version 5.38; Groom et al., 2016 ) revealed fused-ring-substituted chalcones similar to the title compound. There are four compounds that have an anthracene ketone substituent on the chalcone: 9-anthryl styryl ketone and 9,10-anthryl bis(styryl ketone) (CCDC codes: 1827021 and 1827019; Harlow et al., 1975 ), (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one (CCDC 1494027 and 1494026; Girisha et al., 2016 ) and (E)-1-(anthracen-9-yl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one (CCDC 1470351; Abdullah et al., 2016 ). Zainuri et al. (2018a ,b ) reported two anthracene substituents on the chalcone (E)-1,3-bis(anthracen-9-yl)prop-2-en-1-one (CCDC 1817217). Other related compounds include 1-(anthracen-9-yl)-2-methylprop- 2-en-1-one (CCDC 1817219; Agrahari et al., 2015 ) and 9-anthroylacetone (CCDC 1817253; Cicogna et al., 2004 ). For triphenylamine derivatives, Lin et al. (2010) reported a compound with the triphenylamine moiety in a similar propeller-type shape (CCDC 1051418), with dihedral angles between the mean planes of pairs of rings of 71.6 (2), 69.7 (1) and 65.8 (2)°, which is comparable with the title compound.

6. Synthesis and crystallization

To a 100 ml methanol solution of 4-(diphenylamino) benzaldehyde (1.37 g, 5.0 mmol) was added 2-acetylpridine (0.61 g, 5.0 mmol). The mixture was stirred for 2 h at room temperature. The yellow precipitate formed was collected by filtration, and washed sequentially with water and methanol for three times, respectively. Removal of the solvent in vacuo followed by recrystallization from methanol (4 ml) afforded crystals of the title compound suitable for single crystal X-ray studies.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were positioned geometrically and constrained to ride on their parent atoms. The (C1–C6) phenyl ring is disordered over two sets of sites with a refined occupancy ratio of 0.55 (3):0.45 (3). The ring geometries were regularized using soft restraints.

Table 2
Experimental details

Crystal data
Chemical formula	C₃₀H₂₃NO₂
M_r	429.49
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	9.6337 (1), 9.8825 (2), 12.8446 (3)
α, β, γ (°)	87.546 (2), 86.605 (1), 70.914 (3)
V (Å³)	1153.26 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.24 × 0.20

Data collection
Diffractometer	Bruker D8 VENTURE diffractometer with PHOTON II detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.786, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	17043, 4720, 3564
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.03
No. of reflections	4720
No. of parameters	353
No. of restraints	186
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), publCIF (Westrip, 2010 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2406922

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989024011721/wm5735sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024011721/wm5735Isup2.hkl

checkCIF report

Computing details top

(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one top

Crystal data top

C₃₀H₂₃NO₂	Z = 2
M_r = 429.49	F(000) = 452
Triclinic, P1	D_x = 1.237 Mg m⁻³
a = 9.6337 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8825 (2) Å	Cell parameters from 4720 reflections
c = 12.8446 (3) Å	θ = 1.6–26.5°
α = 87.546 (2)°	µ = 0.08 mm⁻¹
β = 86.605 (1)°	T = 293 K
γ = 70.914 (3)°	Block, colourless
V = 1153.26 (4) Å³	0.29 × 0.24 × 0.20 mm

Data collection top

Bruker D8 VENTURE diffractometer with PHOTON II detector	4720 independent reflections
Radiation source: fine-focus sealed tube	3564 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and φ scan	θ_max = 26.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→11
T_min = 0.786, T_max = 0.841	k = −12→12
17043 measured reflections	l = −15→16

Refinement top

Refinement on F²	186 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0573P)² + 0.1568P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4720 reflections	Δρ_max = 0.14 e Å⁻³
353 parameters	Δρ_min = −0.18 e Å⁻³

Special details top

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1A	0.8450 (13)	0.3165 (18)	0.3291 (11)	0.0477 (19)	0.55 (3)
C2A	0.9929 (12)	0.2650 (13)	0.2998 (8)	0.0526 (15)	0.55 (3)
H2A	1.057776	0.201128	0.344055	0.063*	0.55 (3)
C3A	1.0457 (13)	0.3066 (13)	0.2066 (9)	0.0686 (18)	0.55 (3)
H3A	1.145916	0.271704	0.189096	0.082*	0.55 (3)
C4A	0.9533 (17)	0.3982 (14)	0.1395 (7)	0.080 (2)	0.55 (3)
H4A	0.990125	0.423346	0.075644	0.095*	0.55 (3)
C5A	0.8058 (17)	0.4535 (13)	0.1660 (7)	0.077 (2)	0.55 (3)
H5A	0.742187	0.517295	0.121020	0.092*	0.55 (3)
C6A	0.7529 (14)	0.4126 (16)	0.2612 (10)	0.063 (2)	0.55 (3)
H6A	0.653223	0.450652	0.279674	0.076*	0.55 (3)
C1B	0.8233 (15)	0.328 (2)	0.3218 (12)	0.045 (2)	0.45 (3)
C2B	0.9676 (15)	0.2842 (17)	0.2828 (11)	0.058 (2)	0.45 (3)
H2B	1.039659	0.215152	0.318986	0.070*	0.45 (3)
C3B	1.0043 (14)	0.3432 (17)	0.1894 (10)	0.066 (2)	0.45 (3)
H3B	1.100923	0.314279	0.162368	0.079*	0.45 (3)
C4B	0.8958 (17)	0.4449 (16)	0.1379 (7)	0.068 (2)	0.45 (3)
H4B	0.918844	0.485488	0.075329	0.082*	0.45 (3)
C5B	0.7523 (15)	0.4875 (14)	0.1782 (9)	0.069 (2)	0.45 (3)
H5B	0.679939	0.556822	0.142379	0.082*	0.45 (3)
C6B	0.7147 (14)	0.4297 (18)	0.2698 (11)	0.0530 (18)	0.45 (3)
H6B	0.617789	0.458367	0.296255	0.064*	0.45 (3)
C7	0.65146 (14)	0.24068 (14)	0.42815 (10)	0.0489 (3)
C8	0.61478 (18)	0.16550 (16)	0.35241 (12)	0.0652 (4)
H8	0.678822	0.132399	0.295076	0.078*
C9	0.4812 (2)	0.13957 (19)	0.36246 (15)	0.0819 (5)
H9	0.455737	0.089729	0.311064	0.098*
C10	0.3869 (2)	0.1863 (2)	0.44679 (16)	0.0889 (6)
H10	0.298374	0.167343	0.453336	0.107*
C11	0.42347 (19)	0.2606 (2)	0.52096 (14)	0.0865 (6)
H11	0.359410	0.292737	0.578450	0.104*
C12	0.55364 (16)	0.28890 (19)	0.51205 (11)	0.0660 (4)
H12	0.576464	0.341157	0.563074	0.079*
C13	0.87208 (14)	0.24616 (14)	0.51006 (10)	0.0481 (3)
C14	0.94811 (16)	0.33765 (16)	0.53177 (11)	0.0594 (4)
H14	0.943729	0.415330	0.487056	0.071*
C15	1.03041 (15)	0.31498 (15)	0.61902 (11)	0.0558 (3)
H15	1.080387	0.378125	0.632154	0.067*
C16	1.04042 (13)	0.20048 (13)	0.68753 (9)	0.0459 (3)
C17	0.96304 (15)	0.10926 (14)	0.66508 (10)	0.0529 (3)
H17	0.967085	0.031665	0.709799	0.063*
C18	0.88078 (15)	0.13138 (14)	0.57822 (10)	0.0531 (3)
H18	0.830398	0.068598	0.565046	0.064*
C19	1.12578 (14)	0.18198 (14)	0.77995 (10)	0.0510 (3)
H19	1.174152	0.248200	0.787474	0.061*
C20	1.14274 (14)	0.08214 (14)	0.85454 (10)	0.0508 (3)
H20	1.098158	0.012326	0.849705	0.061*
C21	1.23054 (16)	0.07921 (15)	0.94488 (11)	0.0567 (3)
C22	1.25937 (14)	−0.04205 (14)	1.02197 (10)	0.0504 (3)
C23	1.34822 (18)	−0.04494 (16)	1.10440 (11)	0.0626 (4)
H23	1.384847	0.030279	1.111044	0.075*
C24	1.38253 (19)	−0.15626 (16)	1.17565 (11)	0.0671 (4)
H24	1.442908	−0.156542	1.229593	0.081*
C25	1.32810 (16)	−0.26811 (14)	1.16796 (10)	0.0548 (3)
C26	1.23931 (15)	−0.26825 (15)	1.08761 (11)	0.0564 (3)
H26	1.202191	−0.343312	1.081871	0.068*
C27	1.20619 (15)	−0.15555 (15)	1.01576 (11)	0.0552 (3)
H27	1.146378	−0.155960	0.961620	0.066*
C28	1.31454 (19)	−0.49115 (16)	1.24225 (12)	0.0678 (4)
H28A	1.208519	−0.454902	1.237709	0.081*
H28B	1.336179	−0.545667	1.307320	0.081*
C29	1.37787 (16)	−0.58578 (15)	1.15584 (11)	0.0583 (4)
C30	1.4256 (2)	−0.66103 (18)	1.08611 (13)	0.0742 (4)
H30	1.463778	−0.721228	1.030325	0.089*
N1	0.78739 (12)	0.26872 (13)	0.42113 (8)	0.0565 (3)
O1	1.28056 (16)	0.17550 (14)	0.95620 (10)	0.0973 (5)
O2	1.36880 (13)	−0.37308 (11)	1.24355 (7)	0.0704 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.056 (4)	0.050 (3)	0.040 (3)	−0.019 (3)	−0.018 (2)	0.0096 (19)
C2A	0.055 (3)	0.054 (3)	0.052 (3)	−0.022 (2)	−0.005 (2)	0.0072 (19)
C3A	0.075 (4)	0.076 (4)	0.063 (3)	−0.037 (3)	0.006 (3)	0.001 (3)
C4A	0.101 (6)	0.092 (5)	0.055 (3)	−0.047 (5)	−0.001 (4)	0.018 (3)
C5A	0.094 (6)	0.085 (5)	0.054 (3)	−0.033 (4)	−0.023 (4)	0.026 (3)
C6A	0.053 (4)	0.074 (4)	0.060 (3)	−0.017 (4)	−0.015 (3)	0.011 (3)
C1B	0.048 (4)	0.054 (5)	0.037 (4)	−0.023 (3)	−0.004 (3)	0.004 (3)
C2B	0.055 (4)	0.061 (4)	0.059 (4)	−0.018 (3)	−0.009 (3)	0.006 (3)
C3B	0.063 (5)	0.085 (7)	0.054 (4)	−0.033 (4)	0.007 (4)	0.000 (4)
C4B	0.084 (7)	0.086 (5)	0.043 (2)	−0.043 (5)	0.000 (3)	0.011 (3)
C5B	0.073 (5)	0.077 (5)	0.059 (3)	−0.029 (3)	−0.015 (3)	0.020 (3)
C6B	0.046 (4)	0.064 (4)	0.049 (3)	−0.017 (3)	−0.012 (3)	0.015 (3)
C7	0.0489 (7)	0.0559 (7)	0.0442 (7)	−0.0199 (6)	−0.0111 (5)	0.0075 (6)
C8	0.0723 (9)	0.0686 (9)	0.0588 (8)	−0.0265 (8)	−0.0104 (7)	−0.0072 (7)
C9	0.0963 (12)	0.0799 (11)	0.0877 (11)	−0.0487 (10)	−0.0349 (9)	0.0012 (9)
C10	0.0707 (11)	0.1179 (16)	0.0942 (13)	−0.0531 (11)	−0.0211 (8)	0.0259 (11)
C11	0.0581 (10)	0.1348 (17)	0.0706 (11)	−0.0379 (11)	−0.0002 (8)	0.0018 (11)
C12	0.0593 (9)	0.0915 (11)	0.0512 (8)	−0.0285 (8)	−0.0061 (7)	−0.0069 (8)
C13	0.0456 (7)	0.0576 (7)	0.0423 (6)	−0.0187 (6)	−0.0078 (5)	0.0064 (6)
C14	0.0693 (9)	0.0642 (8)	0.0547 (8)	−0.0355 (7)	−0.0186 (7)	0.0207 (7)
C15	0.0609 (8)	0.0604 (8)	0.0556 (8)	−0.0324 (7)	−0.0139 (6)	0.0103 (6)
C16	0.0435 (7)	0.0483 (7)	0.0447 (7)	−0.0130 (5)	−0.0059 (5)	0.0025 (5)
C17	0.0608 (8)	0.0481 (7)	0.0515 (7)	−0.0196 (6)	−0.0139 (6)	0.0104 (6)
C18	0.0600 (8)	0.0525 (7)	0.0537 (7)	−0.0269 (6)	−0.0133 (6)	0.0062 (6)
C19	0.0506 (7)	0.0526 (7)	0.0508 (7)	−0.0172 (6)	−0.0103 (6)	0.0021 (6)
C20	0.0505 (7)	0.0541 (7)	0.0480 (7)	−0.0166 (6)	−0.0102 (6)	0.0024 (6)
C21	0.0609 (8)	0.0593 (8)	0.0529 (8)	−0.0220 (7)	−0.0142 (6)	0.0026 (6)
C22	0.0500 (7)	0.0549 (7)	0.0441 (7)	−0.0128 (6)	−0.0082 (6)	−0.0011 (6)
C23	0.0801 (10)	0.0591 (8)	0.0530 (8)	−0.0257 (7)	−0.0204 (7)	−0.0014 (7)
C24	0.0892 (11)	0.0632 (9)	0.0493 (8)	−0.0209 (8)	−0.0286 (8)	−0.0015 (7)
C25	0.0655 (9)	0.0506 (7)	0.0397 (7)	−0.0065 (6)	−0.0063 (6)	−0.0026 (6)
C26	0.0573 (8)	0.0559 (8)	0.0566 (8)	−0.0179 (6)	−0.0116 (6)	0.0030 (6)
C27	0.0522 (8)	0.0616 (8)	0.0520 (7)	−0.0171 (6)	−0.0169 (6)	0.0041 (6)
C28	0.0854 (11)	0.0581 (8)	0.0522 (8)	−0.0145 (8)	0.0022 (7)	0.0032 (7)
C29	0.0617 (9)	0.0562 (8)	0.0561 (8)	−0.0176 (7)	−0.0079 (7)	0.0037 (7)
C30	0.0855 (12)	0.0692 (10)	0.0657 (10)	−0.0209 (9)	−0.0041 (8)	−0.0113 (8)
N1	0.0544 (7)	0.0804 (8)	0.0422 (6)	−0.0327 (6)	−0.0109 (5)	0.0138 (6)
O1	0.1428 (12)	0.0904 (8)	0.0880 (9)	−0.0721 (9)	−0.0625 (8)	0.0315 (7)
O2	0.1030 (8)	0.0547 (6)	0.0473 (5)	−0.0146 (6)	−0.0214 (5)	0.0021 (4)

Geometric parameters (Å, º) top

C1A—C2A	1.382 (8)	C13—C14	1.3822 (18)
C1A—C6A	1.385 (9)	C13—C18	1.3862 (18)
C1A—N1	1.405 (11)	C13—N1	1.4106 (16)
C2A—C3A	1.372 (8)	C14—C15	1.3792 (19)
C2A—H2A	0.9300	C14—H14	0.9300
C3A—C4A	1.361 (7)	C15—C16	1.3848 (18)
C3A—H3A	0.9300	C15—H15	0.9300
C4A—C5A	1.373 (7)	C16—C17	1.3924 (18)
C4A—H4A	0.9300	C16—C19	1.4552 (17)
C5A—C6A	1.392 (9)	C17—C18	1.3752 (18)
C5A—H5A	0.9300	C17—H17	0.9300
C6A—H6A	0.9300	C18—H18	0.9300
C1B—C6B	1.372 (10)	C19—C20	1.3230 (18)
C1B—C2B	1.383 (10)	C19—H19	0.9300
C1B—N1	1.454 (13)	C20—C21	1.4697 (18)
C2B—C3B	1.389 (9)	C20—H20	0.9300
C2B—H2B	0.9300	C21—O1	1.2161 (17)
C3B—C4B	1.371 (8)	C21—C22	1.4856 (19)
C3B—H3B	0.9300	C22—C27	1.3839 (19)
C4B—C5B	1.382 (8)	C22—C23	1.3940 (18)
C4B—H4B	0.9300	C23—C24	1.367 (2)
C5B—C6B	1.367 (10)	C23—H23	0.9300
C5B—H5B	0.9300	C24—C25	1.379 (2)
C6B—H6B	0.9300	C24—H24	0.9300
C7—C8	1.3775 (19)	C25—O2	1.3658 (16)
C7—C12	1.381 (2)	C25—C26	1.3792 (19)
C7—N1	1.4215 (16)	C26—C27	1.3815 (19)
C8—C9	1.390 (2)	C26—H26	0.9300
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.365 (3)	C28—O2	1.4271 (19)
C9—H9	0.9300	C28—C29	1.454 (2)
C10—C11	1.356 (3)	C28—H28A	0.9700
C10—H10	0.9300	C28—H28B	0.9700
C11—C12	1.369 (2)	C29—C30	1.162 (2)
C11—H11	0.9300	C30—H30	0.9300
C12—H12	0.9300

C2A—C1A—C6A	117.4 (8)	C15—C14—C13	120.72 (13)
C2A—C1A—N1	122.0 (9)	C15—C14—H14	119.6
C6A—C1A—N1	120.6 (8)	C13—C14—H14	119.6
C3A—C2A—C1A	121.1 (7)	C14—C15—C16	121.60 (12)
C3A—C2A—H2A	119.5	C14—C15—H15	119.2
C1A—C2A—H2A	119.5	C16—C15—H15	119.2
C4A—C3A—C2A	120.9 (6)	C15—C16—C17	117.20 (11)
C4A—C3A—H3A	119.6	C15—C16—C19	119.95 (12)
C2A—C3A—H3A	119.6	C17—C16—C19	122.83 (12)
C3A—C4A—C5A	120.0 (6)	C18—C17—C16	121.44 (12)
C3A—C4A—H4A	120.0	C18—C17—H17	119.3
C5A—C4A—H4A	120.0	C16—C17—H17	119.3
C4A—C5A—C6A	119.0 (6)	C17—C18—C13	120.78 (12)
C4A—C5A—H5A	120.5	C17—C18—H18	119.6
C6A—C5A—H5A	120.5	C13—C18—H18	119.6
C1A—C6A—C5A	121.7 (7)	C20—C19—C16	127.70 (13)
C1A—C6A—H6A	119.2	C20—C19—H19	116.1
C5A—C6A—H6A	119.2	C16—C19—H19	116.1
C6B—C1B—C2B	121.3 (9)	C19—C20—C21	121.40 (13)
C6B—C1B—N1	119.6 (9)	C19—C20—H20	119.3
C2B—C1B—N1	119.0 (10)	C21—C20—H20	119.3
C1B—C2B—C3B	119.7 (8)	O1—C21—C20	120.04 (13)
C1B—C2B—H2B	120.1	O1—C21—C22	119.93 (12)
C3B—C2B—H2B	120.1	C20—C21—C22	120.02 (12)
C4B—C3B—C2B	118.9 (7)	C27—C22—C23	117.38 (13)
C4B—C3B—H3B	120.6	C27—C22—C21	123.91 (12)
C2B—C3B—H3B	120.6	C23—C22—C21	118.70 (13)
C3B—C4B—C5B	120.4 (7)	C24—C23—C22	121.24 (14)
C3B—C4B—H4B	119.8	C24—C23—H23	119.4
C5B—C4B—H4B	119.8	C22—C23—H23	119.4
C6B—C5B—C4B	121.2 (8)	C23—C24—C25	120.35 (13)
C6B—C5B—H5B	119.4	C23—C24—H24	119.8
C4B—C5B—H5B	119.4	C25—C24—H24	119.8
C5B—C6B—C1B	118.4 (9)	O2—C25—C24	115.39 (12)
C5B—C6B—H6B	120.8	O2—C25—C26	124.74 (13)
C1B—C6B—H6B	120.8	C24—C25—C26	119.88 (13)
C8—C7—C12	118.85 (13)	C25—C26—C27	119.20 (13)
C8—C7—N1	121.16 (13)	C25—C26—H26	120.4
C12—C7—N1	119.99 (12)	C27—C26—H26	120.4
C7—C8—C9	119.40 (15)	C26—C27—C22	121.95 (12)
C7—C8—H8	120.3	C26—C27—H27	119.0
C9—C8—H8	120.3	C22—C27—H27	119.0
C10—C9—C8	120.86 (15)	O2—C28—C29	112.91 (13)
C10—C9—H9	119.6	O2—C28—H28A	109.0
C8—C9—H9	119.6	C29—C28—H28A	109.0
C11—C10—C9	119.46 (16)	O2—C28—H28B	109.0
C11—C10—H10	120.3	C29—C28—H28B	109.0
C9—C10—H10	120.3	H28A—C28—H28B	107.8
C10—C11—C12	120.68 (17)	C30—C29—C28	178.59 (17)
C10—C11—H11	119.7	C29—C30—H30	180.0
C12—C11—H11	119.7	C1A—N1—C13	117.1 (6)
C11—C12—C7	120.73 (15)	C1A—N1—C7	123.6 (6)
C11—C12—H12	119.6	C13—N1—C7	119.28 (10)
C7—C12—H12	119.6	C13—N1—C1B	124.9 (8)
C14—C13—C18	118.26 (12)	C7—N1—C1B	115.7 (7)
C14—C13—N1	121.10 (12)	C25—O2—C28	118.79 (11)
C18—C13—N1	120.64 (12)

C6A—C1A—C2A—C3A	−0.7 (13)	C19—C20—C21—C22	−174.11 (12)
N1—C1A—C2A—C3A	176.0 (15)	O1—C21—C22—C27	179.55 (15)
C1A—C2A—C3A—C4A	−1.0 (11)	C20—C21—C22—C27	−1.0 (2)
C2A—C3A—C4A—C5A	1.9 (15)	O1—C21—C22—C23	−2.2 (2)
C3A—C4A—C5A—C6A	−1.0 (16)	C20—C21—C22—C23	177.29 (13)
C2A—C1A—C6A—C5A	2 (2)	C27—C22—C23—C24	0.6 (2)
N1—C1A—C6A—C5A	−175.2 (14)	C21—C22—C23—C24	−177.77 (14)
C4A—C5A—C6A—C1A	−1 (2)	C22—C23—C24—C25	−0.7 (2)
C6B—C1B—C2B—C3B	0.2 (16)	C23—C24—C25—O2	−179.69 (13)
N1—C1B—C2B—C3B	−178.2 (18)	C23—C24—C25—C26	0.4 (2)
C1B—C2B—C3B—C4B	0.1 (12)	O2—C25—C26—C27	−179.91 (13)
C2B—C3B—C4B—C5B	−0.1 (17)	C24—C25—C26—C27	0.0 (2)
C3B—C4B—C5B—C6B	−0.2 (19)	C25—C26—C27—C22	−0.1 (2)
C4B—C5B—C6B—C1B	0 (2)	C23—C22—C27—C26	−0.2 (2)
C2B—C1B—C6B—C5B	−1 (2)	C21—C22—C27—C26	178.08 (13)
N1—C1B—C6B—C5B	177.9 (16)	C2A—C1A—N1—C13	39.6 (15)
C12—C7—C8—C9	−0.3 (2)	C6A—C1A—N1—C13	−143.8 (12)
N1—C7—C8—C9	179.61 (14)	C2A—C1A—N1—C7	−139.5 (9)
C7—C8—C9—C10	−0.7 (3)	C6A—C1A—N1—C7	37.1 (19)
C8—C9—C10—C11	0.9 (3)	C14—C13—N1—C1A	38.7 (8)
C9—C10—C11—C12	−0.1 (3)	C18—C13—N1—C1A	−141.4 (8)
C10—C11—C12—C7	−0.9 (3)	C14—C13—N1—C7	−142.17 (14)
C8—C7—C12—C11	1.1 (2)	C18—C13—N1—C7	37.67 (19)
N1—C7—C12—C11	−178.83 (15)	C14—C13—N1—C1B	33.6 (10)
C18—C13—C14—C15	0.0 (2)	C18—C13—N1—C1B	−146.6 (9)
N1—C13—C14—C15	179.86 (13)	C8—C7—N1—C1A	44.8 (9)
C13—C14—C15—C16	0.2 (2)	C12—C7—N1—C1A	−135.3 (9)
C14—C15—C16—C17	−0.4 (2)	C8—C7—N1—C13	−134.28 (14)
C14—C15—C16—C19	−178.66 (13)	C12—C7—N1—C13	45.62 (19)
C15—C16—C17—C18	0.4 (2)	C8—C7—N1—C1B	49.6 (9)
C19—C16—C17—C18	178.59 (13)	C12—C7—N1—C1B	−130.5 (9)
C16—C17—C18—C13	−0.2 (2)	C6B—C1B—N1—C13	−136.2 (14)
C14—C13—C18—C17	0.0 (2)	C2B—C1B—N1—C13	42.2 (17)
N1—C13—C18—C17	−179.88 (12)	C6B—C1B—N1—C7	40 (2)
C15—C16—C19—C20	177.62 (13)	C2B—C1B—N1—C7	−141.9 (10)
C17—C16—C19—C20	−0.6 (2)	C24—C25—O2—C28	178.75 (13)
C16—C19—C20—C21	−178.67 (13)	C26—C25—O2—C28	−1.4 (2)
C19—C20—C21—O1	5.4 (2)	C29—C28—O2—C25	70.02 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O1ⁱ	0.93	2.55	3.054 (2)	114
C28—H28A···Cg(C7–C12)ⁱⁱ	0.93	2.97	3.853 (2)	153
C30—H30···Cg(C22–C27)ⁱⁱⁱ	0.93	2.72	3.527 (2)	145

Symmetry codes: (i) x, y−1, z; (ii) x−1, y+1, z−1; (iii) −x, −y+2, −z.

Acknowledgements

The authors thank the SAIF, IIT, Madras, India, for the data collection.

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