3-(3-Nitro­phen­yl)-1-[4-(prop-2-yn­yloxy)phen­yl]prop-2-en-1-one

Vinaya; Yeriyur B Basavaraju; Holalagudu A Nagma Banu; Balakrishna Kalluraya; Hemmige S Yathirajan; Rishik Balerao; Ray J Butcher

doi:10.1107/S2414314622009579

. 2022 Oct 4;7(Pt 10):x220957. doi: 10.1107/S2414314622009579

3-(3-Nitrophenyl)-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one

Vinaya ^a, Yeriyur B Basavaraju ^a, Holalagudu A Nagma Banu ^b, Balakrishna Kalluraya ^b, Hemmige S Yathirajan ^a,^*, Rishik Balerao ^c, Ray J Butcher ^d

Editor: M Bolte^e

PMCID: PMC9638063 PMID: 36405853

The molecule of the title compound is almost planar but with a dihedral angle between the two phenyl rings of 19.22 (5)°. In the crystal, molecules are linked by C—H⋯O interactions, forming sheets in the (21 Inline graphic ) plane.

Keywords: crystal structure, nitrobenzene, alkyne, chalcone, phenyl ring

Abstract

The structure of the title compound, C₁₈H₁₃NO₄, shows that the whole molecule is almost planar but with a dihedral angle between the two phenyl rings of 19.22 (5)°. The molecules are linked by C—H⋯O interactions, forming sheets in the (21 Inline graphic ) plane.

Structure description

Chalcones are among the leading bioactive flavonoids, with a therapeutic potential implicated to an array of bioactivities that have been investigated by a series of preclinical and clinical studies. They contain an α-β unsaturated carbonyl system, which is present in open-chain form, and two aromatic rings are joined through three-carbon atoms (Kozlowski et al., 2007 ▸; Raghav & Garg, 2014 ▸). Studies depicting the biological activities of chalcones and their derivatives describe their immense significance as antidiabetic, anticancer, anti-inflammatory, antimicrobial, antioxidant, antiparasitic, psychoactive and neuroprotective agents, and their antioxidant and enzyme inhibitory activities (Lin et al., 2002 ▸; Bhat et al., 2005 ▸; Trivedi et al., 2007 ▸; Lahtchev et al., 2008 ▸; Aneja et al., 2018 ▸).

Chalcone as a privileged structure in medicinal chemistry has been reviewed by Zhuang et al. (2017 ▸). A comprehensive review of chalcone derivatives as antileishmanial agents has also been published (de Mello et al., 2018 ▸). The crystal structures of (2E)-1-(4-methylphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (Butcher et al., 2007 ▸), (2E)-1-(3-bromophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one (Jasinski et al., 2010 ▸), (2E)-3-(3-nitrophenyl)-1-[4-(piperidin-1-yl)phenyl]prop-2-en-1-one (Fun et al., 2012 ▸) and 4′-dimethylamino-3-nitrochalcone, 3-dimethylamino-3′-nitrochalcone and 3′-nitrochalcone (Hall et al., 2020 ▸) have been reported.

The present work describes the synthesis and crystal structure of the title compound 3-(3-nitrophenyl)-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one (Fig. 1 ▸), which crystallizes in the triclinic space group P Inline graphic with one molecule in the asymmetric unit. It consists both a 3-nitrophenyl group and a (prop-2-yn-1-yloxy)benzene group linked to a central chalcone moiety. Even though the C—N bond length is 1.4706 (17) Å and thus single, the nitro group is almost coplanar with its phenyl ring [dihedral angle of 18.94 (6)°] as a result of the steric clash between O1 and H4 and between O2 and H2, respectively. The chalcone group is planar (average deviation from plane of 0.004 Å) and makes dihedral angles of 7.69 (8) and 10.96 (6)° with the 3-nitrophenyl ring and the phenyl ring of the (prop-2-yn-1-yloxy)benzene group, respectively. Lastly, the twist between the two phenyl rings which are linked by the chalcone is 19.22 (5)°.

Diagram of molecules showing the atom-labelling scheme. Atomic displacement parameters are at the 30% probability level.

The molecules are linked by C–H⋯O interactions (Table 1 ▸), which form sheets in the (21 Inline graphic ) plane as shown in Fig. 2 ▸ . There are no π–π interactions between the phenyl rings.

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯O2ⁱ	0.901 (18)	2.519 (18)	3.3927 (18)	163.6 (15)

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Symmetry code: (i) Inline graphic .

Packing diagram for the title compound showing the C–H⋯O interactions linking the molecules into sheets in the (21 ) plane.

Synthesis and crystallization

A well-stirred solution of 1-[4-(prop-2-ynyloxy)phenyl]ethanone (1 g, 1 mmol) in 20 ml of ethanol was added slowly to alcoholic potassium hydroxide (0.48 g, 1.5 mmol). To this solution, m-nitro benzaldehyde (1.03 g, 1.2 mmol) was added. The resulting mixture was stirred at room temperature for 30 min. Then, the separated solid from the reaction mixture was filtered, washed with cold water, dried and recrystallized from ethanol:dimethylformamide mixture (9:1). Golden yellow crystals (yield: 86%, m.p. 453–454 K). The reaction scheme is shown in Fig. 3 ▸. FT–IR: νmax, cm⁻¹ (KBr): 2987 (C—H aliphatic), 2117 (C≡C str), 1650 (C=O), 1518 (asym NO₂ stretch),1444 (sym NO₂ stretch), 1252 (C—O stretch); ¹H NMR (400 MHz, CDCl3, δ p.p.m.): 7.55 (d, 1H, J = 15.7 Hz, olefinic-β), 7.36 (d, 2H, J = 8.8 Hz, Ar—H), 7.28 (d, 2H, J = 8.6 Hz, Ar—H), 7.16 (d, 2H, J = 8.8 Hz, Ar—H), 7.09 (d, 2H, J = 8.3 Hz, Ar—H), 6.73 (d, 1H, J = 15.7 Hz, olefinic-α), 4.46 (s, 2H, O—CH₂), 2.79 (s, 1H, acetylene proton).

Reaction scheme for the synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details for the title compound are summarized in Table 2 ▸.

Table 2. Experimental details.

Crystal data
Chemical formula	C₁₈H₁₃NO₄
M _r	307.29
Crystal system, space group	Triclinic, P
Temperature (K)	100
a, b, c (Å)	7.6534 (16), 8.6079 (15), 11.369 (2)
α, β, γ (°)	94.433 (7), 97.953 (8), 97.019 (7)
V (Å³)	732.8 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.19 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 ▸)
T _min, T _max	0.634, 0.729
No. of measured, independent and observed [I > 2σ(I)] reflections	47166, 3638, 2700
R _int	0.089
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.046, 0.137, 1.08
No. of reflections	3638
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

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Computer programs: APEX2 and SAINT (Bruker, 2016 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2018/3 (Sheldrick, 2015b ▸) and SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314622009579/bt4126sup1.cif

x-07-x220957-sup1.cif^{(1.3MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622009579/bt4126Isup2.hkl

x-07-x220957-Isup2.hkl^{(290.1KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supporting information file. DOI: 10.1107/S2414314622009579/bt4126Isup3.cml

CCDC reference: 2210152

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

Acknowledgments

V is grateful to the DST–PURSE Project, Vignan Bhavana, UOM, for providing research facilities.

full crystallographic data

Crystal data

C₁₈H₁₃NO₄	Z = 2
M_r = 307.29	F(000) = 320
Triclinic, P1	D_x = 1.393 Mg m⁻³
a = 7.6534 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6079 (15) Å	Cell parameters from 9976 reflections
c = 11.369 (2) Å	θ = 2.7–32.9°
α = 94.433 (7)°	µ = 0.10 mm⁻¹
β = 97.953 (8)°	T = 100 K
γ = 97.019 (7)°	Prism, yellow
V = 732.8 (3) Å³	0.33 × 0.19 × 0.14 mm

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Data collection

Bruker APEXII CCD diffractometer	2700 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.089
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 28.3°, θ_min = 2.4°
T_min = 0.634, T_max = 0.729	h = −10→10
47166 measured reflections	k = −11→10
3638 independent reflections	l = −15→15

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Refinement

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: mixed
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0642P)² + 0.1082P] where P = (F_o² + 2F_c²)/3
3638 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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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.

Refinement. The acetylenic H atom was freely refined. All remaining hydrogen atoms were placed geometrically and refined as riding atoms with their U_iso values 1.2 times that of their attached atoms.

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

	x	y	z	U_iso*/U_eq
O1	0.8224 (2)	−0.53179 (13)	0.40582 (11)	0.0732 (4)
O2	0.78869 (16)	−0.48667 (12)	0.22192 (10)	0.0557 (3)
O3	0.38666 (16)	0.19330 (12)	0.03294 (9)	0.0557 (3)
O4	0.12863 (14)	0.82184 (10)	0.22678 (8)	0.0419 (3)
N1	0.79204 (16)	−0.44535 (13)	0.32710 (11)	0.0436 (3)
C1	0.63484 (18)	−0.05300 (15)	0.30785 (12)	0.0358 (3)
C2	0.67213 (17)	−0.20372 (14)	0.27518 (11)	0.0342 (3)
H2A	0.639784	−0.249615	0.195197	0.041*
C3	0.75705 (18)	−0.28509 (15)	0.36138 (12)	0.0362 (3)
C4	0.8101 (2)	−0.22355 (17)	0.47820 (12)	0.0446 (3)
H4A	0.868961	−0.282414	0.535011	0.054*
C5	0.7751 (2)	−0.07331 (18)	0.51018 (13)	0.0518 (4)
H5A	0.811026	−0.027252	0.589874	0.062*
C6	0.6882 (2)	0.00972 (17)	0.42650 (13)	0.0469 (4)
H6A	0.663892	0.112233	0.450078	0.056*
C7	0.54529 (18)	0.03375 (15)	0.21647 (12)	0.0378 (3)
H7A	0.524932	−0.013883	0.136707	0.045*
C8	0.49007 (19)	0.17290 (15)	0.23512 (12)	0.0402 (3)
H8A	0.505167	0.222444	0.314155	0.048*
C9	0.40553 (19)	0.25253 (15)	0.13558 (12)	0.0386 (3)
C10	0.34071 (18)	0.40617 (14)	0.16303 (11)	0.0345 (3)
C11	0.32576 (18)	0.46816 (15)	0.27815 (11)	0.0366 (3)
H11A	0.365827	0.414762	0.344742	0.044*
C12	0.25357 (19)	0.60589 (15)	0.29624 (11)	0.0382 (3)
H12A	0.242477	0.645757	0.374749	0.046*
C13	0.19719 (17)	0.68610 (14)	0.19960 (11)	0.0343 (3)
C14	0.2132 (2)	0.62771 (16)	0.08447 (12)	0.0418 (3)
H14A	0.176033	0.682647	0.018101	0.050*
C15	0.2840 (2)	0.48861 (16)	0.06802 (12)	0.0418 (3)
H15A	0.293985	0.448410	−0.010617	0.050*
C16	0.0652 (2)	0.90385 (15)	0.12751 (12)	0.0412 (3)
H16A	−0.037244	0.838377	0.076985	0.049*
H16B	0.160640	0.926181	0.078194	0.049*
C17	0.01114 (18)	1.05106 (15)	0.17380 (12)	0.0397 (3)
C18	−0.0334 (2)	1.17155 (17)	0.20482 (14)	0.0466 (4)
H18A	−0.067 (2)	1.266 (2)	0.2248 (15)	0.057 (5)*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1189 (11)	0.0461 (6)	0.0560 (7)	0.0324 (7)	−0.0072 (7)	0.0173 (5)
O2	0.0791 (8)	0.0448 (6)	0.0449 (6)	0.0280 (5)	0.0012 (5)	−0.0014 (5)
O3	0.0887 (9)	0.0452 (6)	0.0366 (6)	0.0323 (6)	0.0041 (5)	−0.0009 (4)
O4	0.0605 (6)	0.0339 (5)	0.0339 (5)	0.0210 (4)	0.0040 (4)	0.0022 (4)
N1	0.0506 (7)	0.0363 (6)	0.0440 (7)	0.0146 (5)	−0.0018 (5)	0.0069 (5)
C1	0.0395 (7)	0.0333 (6)	0.0357 (7)	0.0103 (5)	0.0049 (5)	0.0040 (5)
C2	0.0384 (7)	0.0328 (6)	0.0316 (6)	0.0087 (5)	0.0027 (5)	0.0026 (5)
C3	0.0397 (7)	0.0333 (6)	0.0372 (7)	0.0102 (5)	0.0052 (5)	0.0063 (5)
C4	0.0535 (8)	0.0465 (8)	0.0352 (7)	0.0153 (6)	0.0012 (6)	0.0090 (6)
C5	0.0691 (10)	0.0530 (9)	0.0320 (7)	0.0183 (7)	−0.0018 (7)	−0.0026 (6)
C6	0.0633 (9)	0.0391 (7)	0.0388 (7)	0.0179 (7)	0.0032 (6)	−0.0021 (6)
C7	0.0457 (7)	0.0333 (6)	0.0353 (7)	0.0121 (5)	0.0040 (5)	0.0016 (5)
C8	0.0514 (8)	0.0340 (7)	0.0359 (7)	0.0148 (6)	0.0025 (6)	0.0014 (5)
C9	0.0484 (8)	0.0324 (6)	0.0366 (7)	0.0130 (5)	0.0061 (6)	0.0021 (5)
C10	0.0406 (7)	0.0296 (6)	0.0339 (6)	0.0096 (5)	0.0038 (5)	0.0025 (5)
C11	0.0472 (7)	0.0324 (6)	0.0317 (6)	0.0115 (5)	0.0037 (5)	0.0066 (5)
C12	0.0514 (8)	0.0343 (6)	0.0299 (6)	0.0109 (6)	0.0064 (5)	0.0014 (5)
C13	0.0396 (7)	0.0281 (6)	0.0352 (6)	0.0090 (5)	0.0033 (5)	0.0007 (5)
C14	0.0596 (9)	0.0371 (7)	0.0307 (6)	0.0188 (6)	0.0018 (6)	0.0047 (5)
C15	0.0603 (9)	0.0365 (7)	0.0305 (6)	0.0177 (6)	0.0044 (6)	0.0011 (5)
C16	0.0526 (8)	0.0343 (7)	0.0368 (7)	0.0160 (6)	−0.0016 (6)	0.0028 (5)
C17	0.0429 (7)	0.0361 (7)	0.0408 (7)	0.0107 (6)	0.0019 (6)	0.0062 (5)
C18	0.0518 (9)	0.0378 (7)	0.0527 (9)	0.0170 (6)	0.0063 (7)	0.0052 (6)

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Geometric parameters (Å, º)

O1—N1	1.2232 (15)	C8—C9	1.4815 (18)
O2—N1	1.2168 (16)	C8—H8A	0.9500
O3—C9	1.2189 (16)	C9—C10	1.4940 (17)
O4—C13	1.3693 (14)	C10—C15	1.3866 (17)
O4—C16	1.4362 (15)	C10—C11	1.3997 (18)
N1—C3	1.4706 (17)	C11—C12	1.3809 (17)
C1—C2	1.3957 (17)	C11—H11A	0.9500
C1—C6	1.3996 (19)	C12—C13	1.3888 (17)
C1—C7	1.4680 (18)	C12—H12A	0.9500
C2—C3	1.3838 (17)	C13—C14	1.3924 (18)
C2—H2A	0.9500	C14—C15	1.3835 (18)
C3—C4	1.3780 (19)	C14—H14A	0.9500
C4—C5	1.384 (2)	C15—H15A	0.9500
C4—H4A	0.9500	C16—C17	1.4627 (18)
C5—C6	1.380 (2)	C16—H16A	0.9900
C5—H5A	0.9500	C16—H16B	0.9900
C6—H6A	0.9500	C17—C18	1.1746 (19)
C7—C8	1.3295 (17)	C18—H18A	0.901 (18)
C7—H7A	0.9500

C13—O4—C16	116.23 (10)	O3—C9—C10	120.22 (12)
O2—N1—O1	122.80 (12)	C8—C9—C10	118.90 (11)
O2—N1—C3	118.79 (11)	C15—C10—C11	118.06 (11)
O1—N1—C3	118.40 (12)	C15—C10—C9	117.85 (11)
C2—C1—C6	118.12 (12)	C11—C10—C9	124.01 (11)
C2—C1—C7	118.90 (11)	C12—C11—C10	120.89 (11)
C6—C1—C7	122.97 (12)	C12—C11—H11A	119.6
C3—C2—C1	118.80 (12)	C10—C11—H11A	119.6
C3—C2—H2A	120.6	C11—C12—C13	119.98 (12)
C1—C2—H2A	120.6	C11—C12—H12A	120.0
C4—C3—C2	123.22 (12)	C13—C12—H12A	120.0
C4—C3—N1	118.22 (11)	O4—C13—C12	115.58 (11)
C2—C3—N1	118.56 (11)	O4—C13—C14	124.35 (11)
C3—C4—C5	117.94 (12)	C12—C13—C14	120.07 (11)
C3—C4—H4A	121.0	C15—C14—C13	119.11 (12)
C5—C4—H4A	121.0	C15—C14—H14A	120.4
C6—C5—C4	120.11 (13)	C13—C14—H14A	120.4
C6—C5—H5A	119.9	C14—C15—C10	121.89 (12)
C4—C5—H5A	119.9	C14—C15—H15A	119.1
C5—C6—C1	121.80 (13)	C10—C15—H15A	119.1
C5—C6—H6A	119.1	O4—C16—C17	108.45 (11)
C1—C6—H6A	119.1	O4—C16—H16A	110.0
C8—C7—C1	125.96 (12)	C17—C16—H16A	110.0
C8—C7—H7A	117.0	O4—C16—H16B	110.0
C1—C7—H7A	117.0	C17—C16—H16B	110.0
C7—C8—C9	121.55 (12)	H16A—C16—H16B	108.4
C7—C8—H8A	119.2	C18—C17—C16	176.40 (14)
C9—C8—H8A	119.2	C17—C18—H18A	177.0 (11)
O3—C9—C8	120.87 (12)

C6—C1—C2—C3	1.0 (2)	C7—C8—C9—C10	177.91 (13)
C7—C1—C2—C3	179.80 (12)	O3—C9—C10—C15	−9.4 (2)
C1—C2—C3—C4	−1.3 (2)	C8—C9—C10—C15	171.57 (13)
C1—C2—C3—N1	178.51 (11)	O3—C9—C10—C11	167.42 (14)
O2—N1—C3—C4	−161.56 (14)	C8—C9—C10—C11	−11.6 (2)
O1—N1—C3—C4	18.8 (2)	C15—C10—C11—C12	1.2 (2)
O2—N1—C3—C2	18.64 (19)	C9—C10—C11—C12	−175.62 (13)
O1—N1—C3—C2	−160.96 (13)	C10—C11—C12—C13	−1.0 (2)
C2—C3—C4—C5	0.5 (2)	C16—O4—C13—C12	−178.35 (11)
N1—C3—C4—C5	−179.33 (13)	C16—O4—C13—C14	2.0 (2)
C3—C4—C5—C6	0.6 (2)	C11—C12—C13—O4	−179.60 (12)
C4—C5—C6—C1	−0.7 (3)	C11—C12—C13—C14	0.1 (2)
C2—C1—C6—C5	−0.1 (2)	O4—C13—C14—C15	−179.70 (13)
C7—C1—C6—C5	−178.78 (15)	C12—C13—C14—C15	0.7 (2)
C2—C1—C7—C8	175.05 (13)	C13—C14—C15—C10	−0.5 (2)
C6—C1—C7—C8	−6.3 (2)	C11—C10—C15—C14	−0.4 (2)
C1—C7—C8—C9	178.18 (13)	C9—C10—C15—C14	176.58 (13)
C7—C8—C9—O3	−1.1 (2)	C13—O4—C16—C17	−175.40 (11)

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Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O2ⁱ	0.901 (18)	2.519 (18)	3.3927 (18)	163.6 (15)

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Symmetry code: (i) x−1, y+2, z.

Funding Statement

HSY and BK are grateful to UGC, New Delhi, for the award of BSR Faculty Fellowship.

References

Aneja, B., Arif, R., Perwez, A., Napoleon, J. V., Hassan, P., Rizvi, M. M. A., Azam, A., Rahisuddin & Abid, M. (2018). ChemistrySelect, 2018, 3, 2638-2645.
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]
Bruker (2016). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Veena, K. & Narayana, B. (2007). Acta Cryst. E63, o3680.
Fun, H.-K., Chia, T. S., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o974. [DOI] [PMC free article] [PubMed]
Hall, C. L., Hamilton, V., Potticary, J., Cremeens, M. E., Pridmore, N. E., Sparkes, H. A., D’ambruoso, G. D., Warren, S. D., Matsumoto, M. & Hall, S. R. (2020). Acta Cryst. E76, 1599–1604. [DOI] [PMC free article] [PubMed]
Jasinski, J. P., Butcher, R. J., Chidan Kumar, C. S., Yathirajan, H. S. & Mayekar, A. N. (2010). Acta Cryst. E66, o2936–o2937. [DOI] [PMC free article] [PubMed]
Kozlowski, D., Trouillas, P., Calliste, C., Marsal, P., Lazzaroni, R. & Duroux, J. L. (2007). J. Phys. Chem. A, 111, 1138–1145. [DOI] [PubMed]
Lahtchev, K. L., Batovska, D. I., Parushev, P., Ubiyvovk, V. M. & Sibirny, A. A. (2008). Eur. J. Med. Chem. 43, 2220–2228. [DOI] [PubMed]
Lin, Y.-M., Zhou, Y., Flavin, M. T., Zhou, L.-M., Nie, W. & Chen, F.-C. (2002). Bioorg. Med. Chem. 10, 2795–2802. [DOI] [PubMed]
Mello, M. V. P. de, Abrahim-Vieira, B. A., Domingos, T. F. S., de Jesus, J. B., de Sousa, A. C. C., Rodrigues, C. R. & Souza, A. M. T. (2018). Eur. J. Med. Chem. 150, 920–929. [DOI] [PubMed]
Raghav, N. & Garg, S. (2014). Eur. J. Pharm. Sci. 60, 55–63. [DOI] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Trivedi, J. C., Bariwal, J. B., Upadhyay, K. D., Naliapara, Y. T., Joshi, S. K., Pannecouque, C. C., De Clercq, E. & Shah, A. K. (2007). Tetrahedron Lett. 48, 8472–8474.
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. & Miao, Z. (2017). Chem. Rev. 117, 7762–7810. [DOI] [PMC free article] [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) I. DOI: 10.1107/S2414314622009579/bt4126sup1.cif

x-07-x220957-sup1.cif^{(1.3MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622009579/bt4126Isup2.hkl

x-07-x220957-Isup2.hkl^{(290.1KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supporting information file. DOI: 10.1107/S2414314622009579/bt4126Isup3.cml

CCDC reference: 2210152

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

[bb1] Aneja, B., Arif, R., Perwez, A., Napoleon, J. V., Hassan, P., Rizvi, M. M. A., Azam, A., Rahisuddin & Abid, M. (2018). ChemistrySelect, 2018, 3, 2638-2645.

[bb2] 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]

[bb3] Bruker (2016). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

[bb4] Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Veena, K. & Narayana, B. (2007). Acta Cryst. E63, o3680.

[bb5] Fun, H.-K., Chia, T. S., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o974. [DOI] [PMC free article] [PubMed]

[bb6] Hall, C. L., Hamilton, V., Potticary, J., Cremeens, M. E., Pridmore, N. E., Sparkes, H. A., D’ambruoso, G. D., Warren, S. D., Matsumoto, M. & Hall, S. R. (2020). Acta Cryst. E76, 1599–1604. [DOI] [PMC free article] [PubMed]

[bb7] Jasinski, J. P., Butcher, R. J., Chidan Kumar, C. S., Yathirajan, H. S. & Mayekar, A. N. (2010). Acta Cryst. E66, o2936–o2937. [DOI] [PMC free article] [PubMed]

[bb8] Kozlowski, D., Trouillas, P., Calliste, C., Marsal, P., Lazzaroni, R. & Duroux, J. L. (2007). J. Phys. Chem. A, 111, 1138–1145. [DOI] [PubMed]

[bb9] Lahtchev, K. L., Batovska, D. I., Parushev, P., Ubiyvovk, V. M. & Sibirny, A. A. (2008). Eur. J. Med. Chem. 43, 2220–2228. [DOI] [PubMed]

[bb10] Lin, Y.-M., Zhou, Y., Flavin, M. T., Zhou, L.-M., Nie, W. & Chen, F.-C. (2002). Bioorg. Med. Chem. 10, 2795–2802. [DOI] [PubMed]

[bb11] Mello, M. V. P. de, Abrahim-Vieira, B. A., Domingos, T. F. S., de Jesus, J. B., de Sousa, A. C. C., Rodrigues, C. R. & Souza, A. M. T. (2018). Eur. J. Med. Chem. 150, 920–929. [DOI] [PubMed]

[bb12] Raghav, N. & Garg, S. (2014). Eur. J. Pharm. Sci. 60, 55–63. [DOI] [PubMed]

[bb13] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb14] Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.

[bb15] Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.

[bb16] Trivedi, J. C., Bariwal, J. B., Upadhyay, K. D., Naliapara, Y. T., Joshi, S. K., Pannecouque, C. C., De Clercq, E. & Shah, A. K. (2007). Tetrahedron Lett. 48, 8472–8474.

[bb17] Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. & Miao, Z. (2017). Chem. Rev. 117, 7762–7810. [DOI] [PMC free article] [PubMed]

PERMALINK

3-(3-Nitrophenyl)-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one

Vinaya

Yeriyur B Basavaraju

Holalagudu A Nagma Banu

Balakrishna Kalluraya

Hemmige S Yathirajan

Rishik Balerao

Ray J Butcher

Roles

Abstract

Structure description