3-Ethyl­indan-1-one

Sonneck, M.; Spannenberg, A.; Wohlrab, S.; Peppel, T.

doi:10.1107/S2414314617016856

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 11| November 2017| x171685

https://doi.org/10.1107/S2414314617016856

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access

3-Ethylindan-1-one

Marcel Sonneck,^a Anke Spannenberg,^a Sebastian Wohlrab ^a and Tim Peppel ^a ^*

^aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
^*Correspondence e-mail: tim.peppel@catalysis.de

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 11 November 2017; accepted 22 November 2017; online 28 November 2017)

The title compound, C₁₁H₁₂O, has been prepared as a side product in the attempted room-temperature synthesis of (E)-1-phenylpent-2-en-1-one. The molecular structure consists of an approximately planar indanone core (r.m.s. deviation = 0.042 Å) with the ethyl group protruding from this plane. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of C—H⋯O hydrogen bonds, forming rings of R₂²(10) graph-set motif. The dimers are further connected by C—H⋯π interactions into chains running parallel to [-101].

Keywords: crystal structure; indanone; liquid.

CCDC reference: 1507153

Structure description

In recent years, new Cu-based complexes suitable for the photocatalytic water-splitting reaction have attracted increasing attention due to their application in sustainable hydrogen-storage technologies (Chen et al., 2017 ). As part of ongoing efforts to synthesize feasible new ligands for these Cu-based complexes (Sonneck et al., 2015 , 2016 ), the title compound was obtained as a side product in the attempted synthesis of the precursor compound (E)-1-phenylpent-2-en-1-one in moderate yield (30%).

The title compound 3-ethylindan-1-one is a racemic ring-closure product of (E)-1-phenylpent-2-en-1-one and the asymmetric unit consists of one indanone molecule (Fig. 1). The indanone ring system is nearly planar [r.m.s. deviation = 0.042 Å; maximum displacement 0.1082 (12) Å for atom C2] with the ethyl group protruding from this plane. All bond lengths and angles are in expected ranges and the C=O bond equals 1.2138 (13) Å. The structure exhibits a typical geometry that corresponds well with that of the parent structure 1-indanone (Morin et al., 1974 ; Peña Ruiz et al., 2004 ).

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

In the crystal structure, centrosymmetric molecules are linked into dimers through pairs of C—H⋯O hydrogen bonds (Table 1), forming rings of R₂²(10) graph-set motif. The dimers are further connected by C—H⋯π interactions, forming chains parallel to [ $[\overline{1}]$ 01].

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C9 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.95	2.52	3.3960 (15)	154
C10—H10B⋯Cg1ⁱⁱ	0.99	2.96	3.7752 (13)	141
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+1, -z.

Synthesis and crystallization

The title compound was obtained as a racemic side product during an attempted room temperature synthesis of (E)-1-phenylpent-2-en-1-one in 30% yield (Ansell & Whitfield, 1968 , 1971 ).

Dry AlCl₃ (41.67 g, 312.53 mmol, 1.5 eq.) was suspended in benzene (81.38 g, 1.04 mol, 5.0 eq.) in a 500 ml two-necked round-bottom flask at 0°C. (E)-Pent-2-enoyl chloride (24.70 g, 208.35 mmol, 1.0 eq.) was added to this suspension dropwise and the remaining solution was further stirred for seven days at 25°C. Afterwards, the solution was poured onto HCl/ice (150 g/50 g), the organic phase was separated and the aqueous phase was extracted with ethyl acetate until it was colorless. The combined organic phases were reduced to a total volume of 150 ml and extracted with brine, afterwards with portions of 10% NaOH solution (250 ml) and again with brine. The organic phase was dried over Na₂SO₄ and the solvent was removed under diminished pressure. The resulting crude product was distilled in vacuo to yield a slightly yellow liquid (10.0 g, 30%, m.p. 289 K). Single crystals were obtained from a distilled sample spontaneously at −30°C over one week.

Analytic data for 3-ethylindan-1-one: m.p. 16°C, b.p. 105°C (6 mbar), ¹H NMR (400 MHz, CDCl₃): δ (p.p.m.): 7.70–7.65 (m, 1H, ArH); 7.57–7.51 (m, 1H, ArH); 7.47–7.43 (m, 1H, ArH); 7.36–7.27 (m, 1H, ArH); 3.31–3.23 (m, 1H); 2.82–2.74 (m, 1H); 2.35–2.26 (m, 1H); 1.95–1.86 (m, 1H); 1.53–1.44 (m, 1H); 0.95–0.89 (m, 3H); ¹³C NMR (100 MHz, CDCl₃): δ (p.p.m.): 206.3 (CO), 158.6, 136.8 (C); 134.5, 127.4, 125.6, 123.4 (CH); 42.5 (CH₂), 39.6 (CH), 28.6 (CH₂); 11.6 (CH₃); MS (EI, 70 eV): m/z = 160 (M⁺, 33), 133 (10), 132 (100), 131 (70), 115 (15), 103 (46), 77 (34), 51 (12); HRMS (ESI–TOF/MS): calculated for C₁₁H₁₂O ([M+H]⁺) 174.10392, found 174.10366; EA for C₁₁H₁₂O % (calc.): C 82.57 (82.46); H 7.62 (7.55).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₁₂O
M_r	160.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	9.0852 (2), 6.4314 (2), 15.5196 (4)
β (°)	102.6361 (10)
V (Å³)	884.85 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.51 × 0.45 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.92, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	10725, 2134, 1793
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.07
No. of reflections	2134
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.16
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2013 ), XP in SHELXTL and SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1507153

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016856/rz4019sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016856/rz4019Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617016856/rz4019Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

3-Ethylindan-1-one top

Crystal data top

C₁₁H₁₂O	F(000) = 344
M_r = 160.21	D_x = 1.203 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.0852 (2) Å	Cell parameters from 5279 reflections
b = 6.4314 (2) Å	θ = 2.7–30.7°
c = 15.5196 (4) Å	µ = 0.08 mm⁻¹
β = 102.6361 (10)°	T = 150 K
V = 884.85 (4) Å³	Prism, colourless
Z = 4	0.51 × 0.45 × 0.29 mm

Data collection top

Bruker APEXII CCD diffractometer	2134 independent reflections
Radiation source: fine-focus sealed tube	1793 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	R_int = 0.019
φ and ω scans	θ_max = 28.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −11→11
T_min = 0.92, T_max = 0.98	k = −8→7
10725 measured reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0531P)² + 0.2028P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2134 reflections	Δρ_max = 0.34 e Å⁻³
110 parameters	Δρ_min = −0.16 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.

Refinement. The H atoms were placed in idealized positions with d(C—H) = 0.95–1.00 Å (CH), 0.99 Å (CH₂), 0.98 Å (CH₃) and refined using a riding model, with U_iso(H) fixed at 1.2 U_eq(C) for CH, CH₂ or 1.5 U_eq(C) for CH₃. A rotating model was used for the methyl group.

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

	x	y	z	U_iso*/U_eq
C1	0.16973 (11)	0.67197 (17)	0.07020 (7)	0.0286 (2)
C2	0.24409 (13)	0.48447 (18)	0.12097 (7)	0.0344 (3)
H2A	0.1796	0.4281	0.1592	0.041*
H2B	0.3429	0.5236	0.1586	0.041*
C3	0.26520 (12)	0.32138 (17)	0.05201 (7)	0.0288 (2)
H3	0.1920	0.2053	0.0520	0.035*
C4	0.22155 (11)	0.43841 (17)	−0.03458 (6)	0.0276 (2)
C5	0.22969 (13)	0.3713 (2)	−0.11876 (7)	0.0354 (3)
H5	0.2658	0.2360	−0.1276	0.042*
C6	0.18401 (13)	0.5057 (2)	−0.18932 (7)	0.0384 (3)
H6	0.1901	0.4619	−0.2469	0.046*
C7	0.12954 (12)	0.7031 (2)	−0.17778 (7)	0.0376 (3)
H7	0.0988	0.7921	−0.2273	0.045*
C8	0.11967 (12)	0.77122 (19)	−0.09466 (7)	0.0335 (3)
H8	0.0818	0.9056	−0.0861	0.040*
C9	0.16722 (11)	0.63589 (17)	−0.02383 (6)	0.0265 (2)
C10	0.42424 (13)	0.2319 (2)	0.06797 (8)	0.0404 (3)
H10A	0.4314	0.1386	0.0183	0.049*
H10B	0.4967	0.3471	0.0686	0.049*
C11	0.46888 (14)	0.1111 (2)	0.15406 (8)	0.0435 (3)
H11A	0.4648	0.2033	0.2038	0.065*
H11B	0.5716	0.0574	0.1604	0.065*
H11C	0.3989	−0.0051	0.1535	0.065*
O1	0.12284 (10)	0.82406 (14)	0.10197 (5)	0.0405 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0289 (5)	0.0301 (6)	0.0270 (5)	−0.0029 (4)	0.0065 (4)	−0.0032 (4)
C2	0.0437 (6)	0.0338 (6)	0.0251 (5)	0.0023 (5)	0.0063 (4)	−0.0007 (4)
C3	0.0310 (5)	0.0280 (5)	0.0273 (5)	−0.0011 (4)	0.0063 (4)	−0.0002 (4)
C4	0.0261 (5)	0.0309 (6)	0.0258 (5)	−0.0017 (4)	0.0055 (4)	−0.0004 (4)
C5	0.0397 (6)	0.0376 (6)	0.0302 (5)	0.0015 (5)	0.0102 (4)	−0.0055 (4)
C6	0.0382 (6)	0.0539 (8)	0.0244 (5)	−0.0026 (5)	0.0095 (4)	−0.0019 (5)
C7	0.0339 (6)	0.0502 (8)	0.0288 (5)	0.0015 (5)	0.0074 (4)	0.0106 (5)
C8	0.0312 (5)	0.0352 (6)	0.0344 (5)	0.0024 (4)	0.0081 (4)	0.0056 (5)
C9	0.0245 (5)	0.0305 (6)	0.0249 (5)	−0.0020 (4)	0.0060 (4)	−0.0008 (4)
C10	0.0370 (6)	0.0472 (7)	0.0379 (6)	0.0082 (5)	0.0101 (5)	0.0056 (5)
C11	0.0379 (6)	0.0454 (7)	0.0451 (7)	0.0091 (5)	0.0043 (5)	0.0097 (5)
O1	0.0504 (5)	0.0356 (5)	0.0363 (4)	0.0062 (4)	0.0115 (4)	−0.0077 (3)

Geometric parameters (Å, º) top

C1—O1	1.2138 (13)	C6—C7	1.3882 (18)
C1—C9	1.4730 (14)	C6—H6	0.9500
C1—C2	1.5161 (16)	C7—C8	1.3836 (17)
C2—C3	1.5402 (15)	C7—H7	0.9500
C2—H2A	0.9900	C8—C9	1.3945 (15)
C2—H2B	0.9900	C8—H8	0.9500
C3—C4	1.5155 (14)	C10—C11	1.5217 (16)
C3—C10	1.5244 (15)	C10—H10A	0.9900
C3—H3	1.0000	C10—H10B	0.9900
C4—C9	1.3858 (15)	C11—H11A	0.9800
C4—C5	1.3931 (14)	C11—H11B	0.9800
C5—C6	1.3859 (16)	C11—H11C	0.9800
C5—H5	0.9500

O1—C1—C9	126.78 (10)	C7—C6—H6	119.3
O1—C1—C2	125.87 (9)	C8—C7—C6	120.49 (11)
C9—C1—C2	107.35 (9)	C8—C7—H7	119.8
C1—C2—C3	106.83 (8)	C6—C7—H7	119.8
C1—C2—H2A	110.4	C7—C8—C9	117.72 (11)
C3—C2—H2A	110.4	C7—C8—H8	121.1
C1—C2—H2B	110.4	C9—C8—H8	121.1
C3—C2—H2B	110.4	C4—C9—C8	122.29 (10)
H2A—C2—H2B	108.6	C4—C9—C1	109.57 (9)
C4—C3—C10	112.74 (9)	C8—C9—C1	128.14 (10)
C4—C3—C2	103.28 (8)	C11—C10—C3	113.36 (10)
C10—C3—C2	113.70 (9)	C11—C10—H10A	108.9
C4—C3—H3	109.0	C3—C10—H10A	108.9
C10—C3—H3	109.0	C11—C10—H10B	108.9
C2—C3—H3	109.0	C3—C10—H10B	108.9
C9—C4—C5	119.36 (10)	H10A—C10—H10B	107.7
C9—C4—C3	112.30 (9)	C10—C11—H11A	109.5
C5—C4—C3	128.34 (10)	C10—C11—H11B	109.5
C6—C5—C4	118.64 (11)	H11A—C11—H11B	109.5
C6—C5—H5	120.7	C10—C11—H11C	109.5
C4—C5—H5	120.7	H11A—C11—H11C	109.5
C5—C6—C7	121.49 (10)	H11B—C11—H11C	109.5
C5—C6—H6	119.3

O1—C1—C2—C3	172.80 (10)	C5—C4—C9—C8	0.11 (15)
C9—C1—C2—C3	−7.95 (11)	C3—C4—C9—C8	−179.72 (9)
C1—C2—C3—C4	7.82 (11)	C5—C4—C9—C1	−179.79 (9)
C1—C2—C3—C10	130.32 (10)	C3—C4—C9—C1	0.38 (12)
C10—C3—C4—C9	−128.37 (10)	C7—C8—C9—C4	−0.64 (16)
C2—C3—C4—C9	−5.23 (11)	C7—C8—C9—C1	179.25 (10)
C10—C3—C4—C5	51.81 (15)	O1—C1—C9—C4	−175.94 (10)
C2—C3—C4—C5	174.95 (11)	C2—C1—C9—C4	4.82 (11)
C9—C4—C5—C6	0.52 (16)	O1—C1—C9—C8	4.16 (18)
C3—C4—C5—C6	−179.68 (10)	C2—C1—C9—C8	−175.08 (10)
C4—C5—C6—C7	−0.64 (17)	C4—C3—C10—C11	−179.14 (10)
C5—C6—C7—C8	0.11 (18)	C2—C3—C10—C11	63.73 (14)
C6—C7—C8—C9	0.52 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 ring

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.95	2.52	3.3960 (15)	154
C10—H10B···Cg1ⁱⁱ	0.99	2.96	3.7752 (13)	141

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

References

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ISSN: 2414-3146

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Ethyl­indan-1-one

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

3-Ethylindan-1-one