(2E)-2-(4-Meth­oxy­benzyl­idene)-2,3-di­hydro-1H-inden-1-one

Asiri, A.M.; Faidallah, H.M.; Al-Nemari, K.F.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006940

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o815

doi:10.1107/S1600536812006940

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(2E)-2-(4-Methoxybenzylidene)-2,3-dihydro-1H-inden-1-one

Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^b Khulud F. Al-Nemari,^a,^b Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 5 February 2012; accepted 16 February 2012; online 24 February 2012)

In the title compound, C₁₇H₁₄O₂, the indan-1-one system is almost planar (r.m.s. deviation = 0.007 Å) and the benzene ring is twisted out of its plane by 8.15 (6)°. The conformation about the C=C double bond [1.348 (2) Å] is E. Helical supramolecular chains along [010] feature in the crystal packing; these are sustained by C—H⋯O hydrogen bonds and π–π interactions between translationally related indan-1-one systems [centroid–centroid distance = 3.7970 (10) Å].

Related literature

For related cyclic ketone structures, see: Asiri, Faidallah & Ng (2011 ); Asiri, Al-Youbi et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₄O₂
M_r = 250.28
Monoclinic, P 2₁ /c
a = 15.1177 (10) Å
b = 3.9322 (3) Å
c = 20.7072 (13) Å
β = 94.615 (6)°
V = 1226.97 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.974, T_max = 0.997
4873 measured reflections
2792 independent reflections
2131 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.126
S = 1.03
2792 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1ⁱ	0.95	2.58	3.5327 (19)	175
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006940/hb6631sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006940/hb6631Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006940/hb6631Isup3.cml

checkCIF report

Comment top

The title compound, 2-(4-methoxybenzylidene)indan-1-one (I), was investigated in connection with recent structure determinations of related cyclic ketone derivatives (Asiri, Faidallah & Ng, 2011; Asiri, Al-Youbi et al., 2011).

The nine non-hydrogen atoms of the inden-1-one system in (I), Fig. 1, are co-planar with a r.m.s. deviation = 0.007 Å. The dihedral angle between the inden-1-one system and benzene ring is 8.15 (6)°, and the methoxy substituent is co-planar with the benzene ring to which it is connected [the C17—O2—C14—C13 torsion angle = -0.6 (2)°]. The configuration about the C9═C10 double bond [1.348 (2) Å] is E.

In the crystal packing, molecules aggregate along the 2₁ axis via C—H···O, Table 1, and π(C1,C2,C7—C9)···π(C2–C7)ⁱ interactions between symmetry related rings of the inden-1-one system [centroid···centroid distance = 3.7970 (10) °, angle between rings = 0.51 (8)° for i: x, -1 + y, z]. There are no specific interactions between the supramolecular chains, Fig. 3.

Related literature top

For related cyclic ketone structures, see: Asiri, Faidallah & Ng (2011); Asiri, Al-Youbi et al. (2011).

Experimental top

A solution of the p-anisaldehyde (1.36 g, 0.01 mol) in ethanol (20 ml) was added to a stirred solution of 1-indanone (1.3 g,0.01 mol) in ethanolic KOH (20%, 20 ml), and stirring was maintained at room temperature for 6 h. The reaction mixture was then poured onto water (200 ml) and set aside overnight. The precipitated solid product was collected by filtration, washed with water, dried and recrystallized from its ethanol solution as light-brown plates, M.pt.: 491–493 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 70% probability level.
	Fig. 2. A view of the helical supramolecular chain along [010] in (I). The C—H···O and π–π interactions are shown as orange and purple dashed lines, respectively.
	Fig. 3. A view in projection down the b axis of the unit-cell contents for (I), highlighting the stacking of chains.

(2E)-2-(4-Methoxybenzylidene)-2,3-dihydro-1H-inden-1-one top

Crystal data top

C₁₇H₁₄O₂	F(000) = 528
M_r = 250.28	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1476 reflections
a = 15.1177 (10) Å	θ = 2.3–27.5°
b = 3.9322 (3) Å	µ = 0.09 mm⁻¹
c = 20.7072 (13) Å	T = 100 K
β = 94.615 (6)°	Plate, light brown
V = 1226.97 (15) Å³	0.30 × 0.30 × 0.03 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2792 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2131 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.7°
ω scan	h = −14→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −3→5
T_min = 0.974, T_max = 0.997	l = −26→22
4873 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.054P)² + 0.3168P] where P = (F_o² + 2F_c²)/3
2792 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₄O₂	V = 1226.97 (15) Å³
M_r = 250.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.1177 (10) Å	µ = 0.09 mm⁻¹
b = 3.9322 (3) Å	T = 100 K
c = 20.7072 (13) Å	0.30 × 0.30 × 0.03 mm
β = 94.615 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2792 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2131 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.997	R_int = 0.030
4873 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2792 reflections	Δρ_min = −0.25 e Å⁻³
172 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.21241 (7)	0.4870 (3)	0.24618 (5)	0.0249 (3)
O2	0.73625 (7)	0.5812 (3)	0.43081 (5)	0.0233 (3)
C1	0.22115 (10)	0.6064 (4)	0.30095 (8)	0.0186 (4)
C2	0.15106 (10)	0.7692 (4)	0.33660 (7)	0.0184 (4)
C3	0.06204 (10)	0.8185 (4)	0.31668 (8)	0.0216 (4)
H3	0.0384	0.7449	0.2751	0.026*
C4	0.00833 (11)	0.9776 (4)	0.35877 (8)	0.0227 (4)
H4	−0.0526	1.0155	0.3460	0.027*
C5	0.04381 (11)	1.0821 (5)	0.42005 (8)	0.0240 (4)
H5	0.0063	1.1894	0.4486	0.029*
C6	0.13295 (11)	1.0321 (4)	0.44003 (8)	0.0215 (4)
H6	0.1565	1.1042	0.4817	0.026*
C7	0.18690 (10)	0.8739 (4)	0.39758 (8)	0.0187 (4)
C8	0.28497 (10)	0.7948 (4)	0.40744 (7)	0.0193 (4)
H8A	0.2978	0.6405	0.4448	0.023*
H8B	0.3203	1.0054	0.4146	0.023*
C9	0.30473 (10)	0.6238 (4)	0.34465 (7)	0.0181 (4)
C10	0.38144 (10)	0.5031 (4)	0.32473 (7)	0.0182 (4)
H10	0.3758	0.3929	0.2838	0.022*
C11	0.47172 (10)	0.5132 (4)	0.35550 (7)	0.0183 (4)
C12	0.53982 (10)	0.3750 (4)	0.32146 (8)	0.0193 (4)
H12	0.5244	0.2673	0.2811	0.023*
C13	0.62868 (10)	0.3885 (4)	0.34408 (8)	0.0200 (4)
H13	0.6731	0.2933	0.3196	0.024*
C14	0.65108 (10)	0.5448 (4)	0.40343 (8)	0.0189 (4)
C15	0.58486 (10)	0.6782 (4)	0.43933 (8)	0.0207 (4)
H15	0.6005	0.7811	0.4802	0.025*
C16	0.49691 (10)	0.6619 (4)	0.41602 (7)	0.0197 (4)
H16	0.4526	0.7524	0.4412	0.024*
C17	0.80559 (10)	0.4433 (5)	0.39500 (8)	0.0242 (4)
H17	0.8629	0.4734	0.4200	0.036*
H17B	0.8063	0.5621	0.3534	0.036*
H17C	0.7948	0.2005	0.3872	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0235 (6)	0.0315 (7)	0.0198 (6)	−0.0012 (5)	0.0025 (5)	−0.0041 (5)
O2	0.0152 (6)	0.0311 (7)	0.0235 (6)	0.0017 (5)	−0.0001 (4)	−0.0045 (5)
C1	0.0193 (8)	0.0181 (8)	0.0187 (8)	−0.0016 (7)	0.0037 (6)	0.0015 (7)
C2	0.0189 (8)	0.0186 (9)	0.0181 (8)	−0.0012 (7)	0.0033 (6)	0.0029 (7)
C3	0.0200 (8)	0.0225 (9)	0.0221 (8)	−0.0033 (7)	0.0009 (6)	0.0017 (7)
C4	0.0171 (8)	0.0248 (9)	0.0263 (8)	0.0013 (7)	0.0023 (6)	0.0050 (8)
C5	0.0221 (8)	0.0261 (9)	0.0247 (9)	0.0028 (8)	0.0077 (7)	0.0027 (8)
C6	0.0235 (8)	0.0215 (9)	0.0195 (8)	0.0010 (7)	0.0023 (6)	0.0006 (7)
C7	0.0189 (8)	0.0169 (8)	0.0202 (8)	−0.0006 (7)	0.0022 (6)	0.0035 (7)
C8	0.0188 (8)	0.0207 (9)	0.0183 (8)	0.0001 (7)	0.0010 (6)	−0.0001 (7)
C9	0.0196 (8)	0.0167 (8)	0.0183 (8)	−0.0011 (7)	0.0029 (6)	0.0015 (7)
C10	0.0217 (8)	0.0174 (8)	0.0158 (7)	−0.0017 (7)	0.0029 (6)	0.0007 (7)
C11	0.0192 (8)	0.0166 (8)	0.0192 (7)	0.0008 (7)	0.0032 (6)	0.0028 (7)
C12	0.0224 (8)	0.0188 (8)	0.0169 (7)	−0.0004 (7)	0.0019 (6)	−0.0008 (7)
C13	0.0189 (8)	0.0214 (9)	0.0203 (8)	0.0028 (7)	0.0051 (6)	0.0013 (7)
C14	0.0168 (8)	0.0196 (8)	0.0202 (8)	0.0003 (7)	0.0008 (6)	0.0034 (7)
C15	0.0237 (8)	0.0222 (9)	0.0160 (7)	0.0029 (7)	0.0014 (6)	−0.0005 (7)
C16	0.0193 (8)	0.0215 (9)	0.0187 (8)	0.0031 (7)	0.0046 (6)	0.0013 (7)
C17	0.0149 (8)	0.0292 (10)	0.0285 (9)	0.0025 (7)	0.0022 (6)	−0.0025 (8)

Geometric parameters (Å, º) top

O1—C1	1.2249 (19)	C8—H8B	0.9900
O2—C14	1.3721 (19)	C9—C10	1.348 (2)
O2—C17	1.4379 (18)	C10—C11	1.460 (2)
C1—C2	1.484 (2)	C10—H10	0.9500
C1—C9	1.495 (2)	C11—C12	1.403 (2)
C2—C3	1.389 (2)	C11—C16	1.407 (2)
C2—C7	1.396 (2)	C12—C13	1.388 (2)
C3—C4	1.387 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.391 (2)
C4—C5	1.399 (2)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.396 (2)
C5—C6	1.392 (2)	C15—C16	1.379 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.393 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9800
C7—C8	1.512 (2)	C17—H17B	0.9800
C8—C9	1.515 (2)	C17—H17C	0.9800
C8—H8A	0.9900

C14—O2—C17	116.51 (12)	C10—C9—C8	130.76 (14)
O1—C1—C2	126.71 (14)	C1—C9—C8	108.93 (13)
O1—C1—C9	126.93 (14)	C9—C10—C11	130.85 (15)
C2—C1—C9	106.35 (13)	C9—C10—H10	114.6
C3—C2—C7	121.58 (15)	C11—C10—H10	114.6
C3—C2—C1	128.75 (15)	C12—C11—C16	116.83 (14)
C7—C2—C1	109.67 (14)	C12—C11—C10	117.92 (14)
C4—C3—C2	118.60 (15)	C16—C11—C10	125.20 (14)
C4—C3—H3	120.7	C13—C12—C11	123.04 (15)
C2—C3—H3	120.7	C13—C12—H12	118.5
C3—C4—C5	120.09 (15)	C11—C12—H12	118.5
C3—C4—H4	120.0	C12—C13—C14	118.37 (14)
C5—C4—H4	120.0	C12—C13—H13	120.8
C6—C5—C4	121.30 (15)	C14—C13—H13	120.8
C6—C5—H5	119.3	O2—C14—C13	124.38 (14)
C4—C5—H5	119.3	O2—C14—C15	115.46 (14)
C5—C6—C7	118.54 (15)	C13—C14—C15	120.16 (14)
C5—C6—H6	120.7	C16—C15—C14	120.57 (15)
C7—C6—H6	120.7	C16—C15—H15	119.7
C6—C7—C2	119.89 (15)	C14—C15—H15	119.7
C6—C7—C8	128.61 (15)	C15—C16—C11	121.01 (14)
C2—C7—C8	111.49 (14)	C15—C16—H16	119.5
C7—C8—C9	103.55 (13)	C11—C16—H16	119.5
C7—C8—H8A	111.1	O2—C17—H17	109.5
C9—C8—H8A	111.1	O2—C17—H17B	109.5
C7—C8—H8B	111.1	H17—C17—H17B	109.5
C9—C8—H8B	111.1	O2—C17—H17C	109.5
H8A—C8—H8B	109.0	H17—C17—H17C	109.5
C10—C9—C1	120.30 (14)	H17B—C17—H17C	109.5

O1—C1—C2—C3	0.6 (3)	C2—C1—C9—C8	0.59 (18)
C9—C1—C2—C3	179.53 (16)	C7—C8—C9—C10	178.56 (17)
O1—C1—C2—C7	−179.84 (16)	C7—C8—C9—C1	−0.04 (17)
C9—C1—C2—C7	−0.96 (18)	C1—C9—C10—C11	174.72 (16)
C7—C2—C3—C4	0.3 (3)	C8—C9—C10—C11	−3.7 (3)
C1—C2—C3—C4	179.78 (16)	C9—C10—C11—C12	−177.64 (17)
C2—C3—C4—C5	−0.5 (3)	C9—C10—C11—C16	0.0 (3)
C3—C4—C5—C6	0.4 (3)	C16—C11—C12—C13	−1.8 (2)
C4—C5—C6—C7	−0.1 (3)	C10—C11—C12—C13	176.01 (15)
C5—C6—C7—C2	−0.1 (2)	C11—C12—C13—C14	0.3 (3)
C5—C6—C7—C8	179.26 (16)	C17—O2—C14—C13	−0.6 (2)
C3—C2—C7—C6	0.0 (3)	C17—O2—C14—C15	179.49 (15)
C1—C2—C7—C6	−179.54 (15)	C12—C13—C14—O2	−178.74 (15)
C3—C2—C7—C8	−179.47 (15)	C12—C13—C14—C15	1.1 (2)
C1—C2—C7—C8	0.97 (19)	O2—C14—C15—C16	178.80 (15)
C6—C7—C8—C9	180.00 (16)	C13—C14—C15—C16	−1.1 (3)
C2—C7—C8—C9	−0.57 (18)	C14—C15—C16—C11	−0.4 (3)
O1—C1—C9—C10	0.7 (3)	C12—C11—C16—C15	1.8 (2)
C2—C1—C9—C10	−178.19 (15)	C10—C11—C16—C15	−175.80 (16)
O1—C1—C9—C8	179.47 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.95	2.58	3.5327 (19)	175

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄O₂
M_r	250.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.1177 (10), 3.9322 (3), 20.7072 (13)
β (°)	94.615 (6)
V (Å³)	1226.97 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.30 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.974, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	4873, 2792, 2131
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.126, 1.03
No. of reflections	2792
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.95	2.58	3.5327 (19)	175

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

King Abdulaziz University is thanked for support. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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