(2E)-2-[(2E)-3-Phenyl-prop-2-en-1-yl-idene]-2,3-dihydro-1H-inden-1-one.

The title indan-1-one derivative, C(18)H(14)O, 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. Supra-molecular layers in the bc plane, mediated by C-H⋯O and π-π [ring centroid-centroid distance = 3.5282 (15) Å] inter-actions, 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 = 246.29

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.101

S = 1.05

1521 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007131/pv2516sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812007131/pv2516Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H14O	F(000) = 520
Mr = 246.29	Dx = 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

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	Rint = 0.035
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.8°
ω scan	h = −21→38
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −3→4
Tmin = 0.981, Tmax = 0.992	l = −14→9
3652 measured reflections

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(Fo2) + (0.0502P)2 + 0.2004P] where P = (Fo2 + 2Fc2)/3
1521 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .