(2E)-2-[(2E)-3-Phenyl­prop-2-en-1-yl­idene]-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/S1600536812007131

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o814

doi:10.1107/S1600536812007131

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(2E)-2-[(2E)-3-Phenylprop-2-en-1-ylidene]-2,3-dihydro-1H-inden-1-one

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

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

(Received 14 February 2012; accepted 16 February 2012; online 24 February 2012)

The title indan-1-one derivative, C₁₈H₁₄O, is planar with an r.m.s. deviation for all 19 non-H atoms of 0.098 Å. The conformation about each of the C=C bonds [1.343 (3) and 1.349 (3) Å] is E. Supramolecular layers in the bc plane, mediated by C—H⋯O and π–π [ring centroid–centroid distance = 3.5282 (15) Å] interactions, feature in the crystal packing.

Related literature

For the activity of related species developed for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009 ). For the crystal structure of a closely related compound, see: Magomedova et al. (1980 ).

Experimental

Crystal data

C₁₈H₁₄O
M_r = 246.29
Orthorhombic, P c a 2₁
a = 29.192 (4) Å
b = 3.9110 (3) Å
c = 11.2025 (7) Å
V = 1279.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.981, T_max = 0.992
3652 measured reflections
1521 independent reflections
1375 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.101
S = 1.05
1521 reflections
172 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.99	2.58	3.432 (3)	144
Symmetry code: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

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: ORTEP-3 (Farrugia, 1997 ) 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/S1600536812007131/pv2516sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007131/pv2516Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007131/pv2516Isup3.cml

checkCIF report

Comment top

The title compound (I), was investigated owing to its relationship to some active compounds developed for the treatment of Chagas disease (Vera-DiVaio et al., 2009).

The molecule of (I) (Fig. 1), is planar with a r.m.s. deviation for all 19 non-hydrogen atoms = 0.098 Å. The maximum deviations are found for the C12 [0.138 (2) Å] and C15 [-0.154 (3) Å] atoms. The configuration about the C9═C10 bond [1.343 (3) Å] is E and a similar configuration is found for the C11═C12 bond [1.349 (3) Å].

In the crystal packing, C—H···O (Table 1), and π–π [ring centroid(C1,C2,C7–C9)···centroid(C2–C7)ⁱ distance = 3.5282 (15) Å, angle between planes = 1.49 (13)°, for symmetry operation i: x, 1 + y, z] interactions link molecules into layers in the bc plane (Fig. 2). The layers stack along the a axis with no specific interactions between them (Fig. 2).

Related literature top

For the activity of related species developed for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009). For the crystal structure of a closely related compound, see: Magomedova et al. (1980) or (2009).

Experimental top

A solution of cinnamaldehyde (1.3 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 product was collected by filtration, washed with water, dried and recrystallized from its ethanol solution as prisms, m.p.: 390–391 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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular layer in the bc plane 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 c axis of the unit-cell contents of (I). The C—H···O and π–π interactions are shown as orange and purple dashed lines, respectively.

(2E)-2-[(2E)-3-Phenylprop-2-en-1-ylidene]-2,3-dihydro-1H- inden-1-one top

Crystal data top

C₁₈H₁₄O	F(000) = 520
M_r = 246.29	D_x = 1.279 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1378 reflections
a = 29.192 (4) Å	θ = 2.8–27.5°
b = 3.9110 (3) Å	µ = 0.08 mm⁻¹
c = 11.2025 (7) Å	T = 100 K
V = 1279.0 (2) Å³	Prism, light-brown
Z = 4	0.25 × 0.15 × 0.10 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	1521 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1375 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.035
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.8°
ω scan	h = −21→38
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −3→4
T_min = 0.981, T_max = 0.992	l = −14→9
3652 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0502P)² + 0.2004P] where P = (F_o² + 2F_c²)/3
1521 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₄O	V = 1279.0 (2) Å³
M_r = 246.29	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 29.192 (4) Å	µ = 0.08 mm⁻¹
b = 3.9110 (3) Å	T = 100 K
c = 11.2025 (7) Å	0.25 × 0.15 × 0.10 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	1521 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1375 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.992	R_int = 0.035
3652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
1521 reflections	Δρ_min = −0.20 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	0.44657 (6)	0.7797 (5)	0.50084 (17)	0.0279 (4)
C1	0.44960 (8)	0.6972 (6)	0.6062 (2)	0.0198 (5)
C2	0.41457 (9)	0.5162 (6)	0.6782 (2)	0.0199 (5)
C3	0.37141 (9)	0.3984 (6)	0.6439 (2)	0.0228 (5)
H3	0.3609	0.4261	0.5642	0.027*
C4	0.34418 (9)	0.2399 (6)	0.7290 (3)	0.0250 (6)
H4	0.3149	0.1542	0.7073	0.030*
C5	0.35962 (9)	0.2057 (6)	0.8465 (2)	0.0250 (6)
H5	0.3405	0.1003	0.9043	0.030*
C6	0.40277 (9)	0.3243 (6)	0.8799 (2)	0.0226 (5)
H6	0.4130	0.3005	0.9600	0.027*
C7	0.43058 (8)	0.4770 (6)	0.7953 (2)	0.0192 (5)
C8	0.47848 (8)	0.6172 (6)	0.8098 (2)	0.0194 (5)
H8A	0.5003	0.4344	0.8323	0.023*
H8B	0.4794	0.7996	0.8710	0.023*
C9	0.48938 (9)	0.7589 (6)	0.6868 (2)	0.0184 (5)
C10	0.52758 (8)	0.9192 (6)	0.6502 (2)	0.0205 (5)
H10	0.5276	1.0052	0.5709	0.025*
C11	0.56849 (8)	0.9734 (6)	0.7194 (2)	0.0199 (5)
H11	0.5694	0.8957	0.7997	0.024*
C12	0.60551 (9)	1.1316 (6)	0.6731 (2)	0.0222 (5)
H12	0.6023	1.2158	0.5940	0.027*
C13	0.65002 (9)	1.1892 (6)	0.7300 (2)	0.0220 (5)
C14	0.68584 (9)	1.3265 (6)	0.6620 (3)	0.0279 (6)
H14	0.6805	1.3881	0.5811	0.033*
C15	0.72899 (9)	1.3738 (7)	0.7109 (3)	0.0310 (6)
H15	0.7530	1.4639	0.6630	0.037*
C16	0.73741 (9)	1.2911 (7)	0.8289 (3)	0.0317 (7)
H16	0.7669	1.3262	0.8625	0.038*
C17	0.70216 (9)	1.1559 (7)	0.8976 (3)	0.0290 (6)
H17	0.7078	1.0967	0.9785	0.035*
C18	0.65895 (9)	1.1062 (7)	0.8501 (2)	0.0234 (6)
H18	0.6352	1.0157	0.8986	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0310 (10)	0.0385 (11)	0.0142 (8)	0.0023 (8)	−0.0007 (8)	0.0023 (8)
C1	0.0217 (12)	0.0194 (11)	0.0183 (11)	0.0062 (9)	−0.0006 (10)	−0.0037 (11)
C2	0.0244 (12)	0.0157 (11)	0.0197 (11)	0.0054 (10)	0.0024 (10)	−0.0018 (10)
C3	0.0241 (13)	0.0201 (11)	0.0242 (12)	0.0047 (10)	−0.0054 (11)	−0.0020 (11)
C4	0.0215 (12)	0.0218 (13)	0.0317 (15)	0.0015 (10)	0.0014 (12)	−0.0006 (12)
C5	0.0255 (14)	0.0203 (12)	0.0292 (14)	0.0031 (10)	0.0056 (11)	0.0025 (11)
C6	0.0286 (14)	0.0197 (12)	0.0194 (12)	0.0044 (10)	0.0019 (11)	0.0023 (11)
C7	0.0225 (12)	0.0147 (11)	0.0205 (11)	0.0063 (9)	−0.0015 (10)	−0.0039 (10)
C8	0.0231 (13)	0.0204 (12)	0.0147 (11)	0.0025 (9)	−0.0015 (10)	−0.0022 (10)
C9	0.0218 (12)	0.0182 (11)	0.0153 (11)	0.0039 (9)	0.0000 (9)	−0.0014 (10)
C10	0.0267 (12)	0.0181 (11)	0.0166 (10)	0.0048 (9)	0.0014 (10)	0.0001 (10)
C11	0.0224 (13)	0.0209 (12)	0.0164 (11)	0.0026 (10)	0.0015 (10)	−0.0001 (11)
C12	0.0280 (13)	0.0185 (12)	0.0203 (12)	0.0018 (9)	0.0008 (11)	−0.0007 (11)
C13	0.0261 (13)	0.0163 (12)	0.0235 (13)	0.0004 (9)	0.0033 (12)	−0.0048 (11)
C14	0.0297 (14)	0.0248 (13)	0.0292 (14)	−0.0030 (10)	0.0052 (12)	−0.0043 (12)
C15	0.0265 (14)	0.0284 (14)	0.0382 (16)	−0.0047 (11)	0.0089 (13)	−0.0055 (13)
C16	0.0236 (14)	0.0299 (14)	0.0417 (17)	−0.0004 (11)	−0.0039 (13)	−0.0105 (14)
C17	0.0307 (15)	0.0295 (13)	0.0268 (14)	0.0020 (12)	−0.0056 (12)	−0.0048 (12)
C18	0.0240 (13)	0.0247 (13)	0.0215 (12)	−0.0007 (10)	0.0024 (11)	−0.0015 (11)

Geometric parameters (Å, º) top

O1—C1	1.227 (3)	C10—C11	1.439 (3)
C1—C2	1.482 (3)	C10—H10	0.9500
C1—C9	1.491 (3)	C11—C12	1.349 (3)
C2—C3	1.396 (3)	C11—H11	0.9500
C2—C7	1.401 (3)	C12—C13	1.465 (3)
C3—C4	1.388 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.401 (4)
C4—C5	1.398 (4)	C13—C18	1.408 (4)
C4—H4	0.9500	C14—C15	1.386 (4)
C5—C6	1.393 (4)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.382 (4)
C6—C7	1.383 (4)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.390 (4)
C7—C8	1.511 (3)	C16—H16	0.9500
C8—C9	1.518 (3)	C17—C18	1.383 (4)
C8—H8A	0.9900	C17—H17	0.9500
C8—H8B	0.9900	C18—H18	0.9500
C9—C10	1.343 (3)

O1—C1—C2	126.8 (2)	C1—C9—C8	109.1 (2)
O1—C1—C9	126.6 (2)	C9—C10—C11	126.4 (2)
C2—C1—C9	106.6 (2)	C9—C10—H10	116.8
C3—C2—C7	121.5 (2)	C11—C10—H10	116.8
C3—C2—C1	129.1 (2)	C12—C11—C10	121.7 (2)
C7—C2—C1	109.4 (2)	C12—C11—H11	119.2
C4—C3—C2	118.4 (3)	C10—C11—H11	119.2
C4—C3—H3	120.8	C11—C12—C13	127.9 (2)
C2—C3—H3	120.8	C11—C12—H12	116.1
C3—C4—C5	120.3 (3)	C13—C12—H12	116.1
C3—C4—H4	119.8	C14—C13—C18	118.0 (2)
C5—C4—H4	119.8	C14—C13—C12	118.9 (2)
C6—C5—C4	120.8 (2)	C18—C13—C12	123.0 (2)
C6—C5—H5	119.6	C15—C14—C13	120.9 (3)
C4—C5—H5	119.6	C15—C14—H14	119.5
C7—C6—C5	119.4 (2)	C13—C14—H14	119.5
C7—C6—H6	120.3	C16—C15—C14	120.6 (3)
C5—C6—H6	120.3	C16—C15—H15	119.7
C6—C7—C2	119.5 (2)	C14—C15—H15	119.7
C6—C7—C8	128.8 (2)	C15—C16—C17	119.2 (3)
C2—C7—C8	111.7 (2)	C15—C16—H16	120.4
C7—C8—C9	103.25 (19)	C17—C16—H16	120.4
C7—C8—H8A	111.1	C18—C17—C16	121.0 (3)
C9—C8—H8A	111.1	C18—C17—H17	119.5
C7—C8—H8B	111.1	C16—C17—H17	119.5
C9—C8—H8B	111.1	C17—C18—C13	120.3 (2)
H8A—C8—H8B	109.1	C17—C18—H18	119.8
C10—C9—C1	122.5 (2)	C13—C18—H18	119.8
C10—C9—C8	128.4 (2)

O1—C1—C2—C3	0.5 (4)	O1—C1—C9—C8	179.6 (2)
C9—C1—C2—C3	−179.3 (2)	C2—C1—C9—C8	−0.5 (3)
O1—C1—C2—C7	−178.5 (2)	C7—C8—C9—C10	178.8 (2)
C9—C1—C2—C7	1.6 (3)	C7—C8—C9—C1	−0.7 (2)
C7—C2—C3—C4	0.1 (4)	C1—C9—C10—C11	−176.3 (2)
C1—C2—C3—C4	−178.8 (2)	C8—C9—C10—C11	4.3 (4)
C2—C3—C4—C5	1.1 (4)	C9—C10—C11—C12	178.5 (2)
C3—C4—C5—C6	−1.1 (4)	C10—C11—C12—C13	−176.6 (2)
C4—C5—C6—C7	−0.1 (4)	C11—C12—C13—C14	173.1 (2)
C5—C6—C7—C2	1.3 (3)	C11—C12—C13—C18	−5.5 (4)
C5—C6—C7—C8	−178.7 (2)	C18—C13—C14—C15	1.1 (4)
C3—C2—C7—C6	−1.3 (3)	C12—C13—C14—C15	−177.6 (2)
C1—C2—C7—C6	177.8 (2)	C13—C14—C15—C16	−1.0 (4)
C3—C2—C7—C8	178.7 (2)	C14—C15—C16—C17	0.7 (4)
C1—C2—C7—C8	−2.2 (3)	C15—C16—C17—C18	−0.6 (4)
C6—C7—C8—C9	−178.2 (2)	C16—C17—C18—C13	0.6 (4)
C2—C7—C8—C9	1.8 (2)	C14—C13—C18—C17	−0.9 (4)
O1—C1—C9—C10	0.1 (4)	C12—C13—C18—C17	177.8 (2)
C2—C1—C9—C10	180.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.99	2.58	3.432 (3)	144

Symmetry code: (i) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O
M_r	246.29
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	29.192 (4), 3.9110 (3), 11.2025 (7)
V (Å³)	1279.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.15 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.981, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	3652, 1521, 1375
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.101, 1.05
No. of reflections	1521
No. of parameters	172
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) 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
C8—H8A···O1ⁱ	0.99	2.58	3.432 (3)	144

Symmetry code: (i) −x+1, −y+1, z+1/2.

Footnotes

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

Acknowledgements

The authors are thankful to the Center of Excellence for Advanced Materials Research and the Chemistry Department of King Abdulaziz University for providing research facilities. 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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