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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2025 Jan 1;81(Pt 1):15–19. doi: 10.1107/S2056989024011721

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, Devadasan Velmurugan c
Editor: M Weild
PMCID: PMC11701778  PMID: 39776626

The mol­ecule adopts an s-cis conformation with respect to the C=O and C—C bonds of the chalcone bridge.

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

Abstract

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.

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 ▸).1.

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.

Figure 1

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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
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic; (iii) Inline graphic.

Figure 2.

Figure 2

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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 dnorm and two-dimensional fingerprint plots) by using CrystalExplorer (Spackman et al., 2021 ▸). The Hirshfeld surface of the title compound mapped over dnorm is shown in Fig. 3 ▸, where the normalized contact distance, dnorm, 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. 4 ▸a 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. 4 ▸b), H⋯C/C⋯H contacts at 36.7% (Fig. 4 ▸c), and O⋯H/H⋯O at 9.3% (Fig. 4 ▸d). Other contacts, viz. C⋯C at 2.4% (Fig. 4 ▸e), O⋯C/C⋯O at 0.9% (Fig. 4 ▸f) and N⋯H/H⋯N contacts at 0.3% (Fig. 4 ▸g) play a minor role.

Figure 3.

Figure 3

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The Hirshfeld surfaces of the title compound mapped over dnorm.

Figure 4.

Figure 4

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(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, PInline graphic
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 ▸)
Tmin, Tmax 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
Δρmax, Δρmin (e Å−3) 0.14, −0.18
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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 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989024011721/wm5735sup1.cif

e-81-00015-sup1.cif (518KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989024011721/wm5735Isup2.hkl

e-81-00015-Isup2.hkl (375.7KB, hkl)

CCDC reference: 2406922

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

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

C30H23NO2 Z = 2
Mr = 429.49 F(000) = 452
Triclinic, P1 Dx = 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
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(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one . Data collection

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 Rint = 0.027
ω and φ scan θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015) h = −12→11
Tmin = 0.786, Tmax = 0.841 k = −12→12
17043 measured reflections l = −15→16
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(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one . Refinement

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(Fo2) + (0.0573P)2 + 0.1568P] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max = 0.001
4720 reflections Δρmax = 0.14 e Å−3
353 parameters Δρmin = −0.18 e Å−3
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(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one . Special details

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.
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(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq 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)
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(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one . Atomic displacement parameters (Å2)

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)
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(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one . Geometric parameters (Å, º)

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)
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(2E)-3-[4-(Diphenylamino)phenyl]-1-[4-(prop-1-yn-2-yloxy)phenyl]prop-2-en-1-one . Hydrogen-bond geometry (Å, º)

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

References

  1. Abdullah, A. A., Hassan, N. H. H., Arshad, S., Khalib, N. C. & Razak, I. A. (2016). Acta Cryst. E72, 648–651. [DOI] [PMC free article] [PubMed]
  2. Agrahari, A., Wagers, P. O., Schildcrout, S. M., Masnovi, J. & Youngs, W. J. (2015). Acta Cryst. E71, 357–359. [DOI] [PMC free article] [PubMed]
  3. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  4. Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett.15, 3177–3180. [DOI] [PubMed]
  5. Botek, E., Champagne, B., Turki, M. & André, J. M. (2004). J. Chem. Phys.120, 2042–2048. [DOI] [PubMed]
  6. Bruker (2016). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  7. Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj, K. K. (2006). Acta Cryst. E62, o1973–o1975.
  8. Cicogna, F., Ingrosso, G., Lodato, F., Marchetti, F. & Zandomeneghi, M. (2004). Tetrahedron, 60, 11959–11968.
  9. Farrugia, L. J. (2012). J. Appl. Cryst.45, 849–854.
  10. Girisha, M., Yathirajan, H. S., Jasinski, J. P. & Glidewell, C. (2016). Acta Cryst. E72, 1153–1158. [DOI] [PMC free article] [PubMed]
  11. Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
  12. Harlow, R. L., Loghry, R. A., Williams, H. J. & Simonsen, S. H. (1975). Acta Cryst. B31, 1344–1350.
  13. Jung, Y., Son, K., Oh, Y. E. & Noh, D. (2008). Polyhedron, 27, 861–867.
  14. Kozlowski, D., Trouillas, P., Calliste, C., Marsal, P., Lazzaroni, R. & Duroux, J.-L. (2007). J. Phys. Chem. A, 111, 1138–1145. [DOI] [PubMed]
  15. Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst.48, 3–10. [DOI] [PMC free article] [PubMed]
  16. Lin, L. Y., Tsai, C. H., Wong, K. T., Huang, T. W., Hsieh, L., Liu, S. H., Lin, H. W., Wu, C. C., Chou, S. H., Chen, S. H. & Tsai, A. I. (2010). J. Org. Chem.75, 4778–4785. [DOI] [PubMed]
  17. Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst.41, 466–470.
  18. Madan, B., Batra, S. & Ghosh, B. (2000). Mol. Pharmacol.58, 526–534. [DOI] [PubMed]
  19. McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]
  20. Nizam Mohideen, M., Thenmozhi, S., Subbiah Pandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4379.
  21. Ravishankar, T., Chinnakali, K., Nanjundan, S., Selvam, P., Fun, H.-K. & Yu, X.-L. (2005). Acta Cryst. E61, o405–o407.
  22. Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
  23. Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
  24. Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32.
  25. Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst.54, 1006–1011. [DOI] [PMC free article] [PubMed]
  26. Spek, A. L. (2020). Acta Cryst. E76, 1–11. [DOI] [PMC free article] [PubMed]
  27. Tan, S. L., Jotani, M. M. & Tiekink, E. R. T. (2019). Acta Cryst. E75, 308–318. [DOI] [PMC free article] [PubMed]
  28. Toledo, T. A. de, da Costa, R. C., Bento, R. R. F., Al-Maqtari, H. M., Jamalis, J. & Pizani, P. S. (2018). J. Mol. Struct.1155, 634–645.
  29. Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  30. Xue, C. X., Cui, S. Y., Liu, M. C., Hu, D. & Fan, B. T. (2004). Eur. J. Med. Chem.39, 745–753. [DOI] [PubMed]
  31. Yayli, N., Ucuncu, O., Yasar, A., Kucuk, M., Yayli, N., Akyuz, E. & Alpay-Karaoglu, S. (2006). Turk. J. Chem.30, 505–514.
  32. Zainuri, D. A., Razak, I. A. & Arshad, S. (2018a). Acta Cryst. E74, 492–496. [DOI] [PMC free article] [PubMed]
  33. Zainuri, D. A., Razak, I. A. & Arshad, S. (2018b). Acta Cryst. E74, 650–655. [DOI] [PMC free article] [PubMed]
  34. Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Bioorg. Med. Chem. Lett.15, 5027–5029. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989024011721/wm5735sup1.cif

e-81-00015-sup1.cif (518KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989024011721/wm5735Isup2.hkl

e-81-00015-Isup2.hkl (375.7KB, hkl)

CCDC reference: 2406922

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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