(2E)-2-(4-Meth-oxy-benzyl-idene)-2,3-di-hydro-1H-inden-1-one.

In the title compound, C(17)H(14)O(2), 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 supra-molecular chains along [010] feature in the crystal packing; these are sustained by C-H⋯O hydrogen bonds and π-π inter-actions 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 = 250.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.126

S = 1.03

2792 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 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: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006940/hb6631sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812006940/hb6631Isup3.cml

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

C17H14O2	F(000) = 528
Mr = 250.28	Dx = 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

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	Rint = 0.030
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −14→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −3→5
Tmin = 0.974, Tmax = 0.997	l = −26→22
4873 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.054P)2 + 0.3168P] where P = (Fo2 + 2Fc2)/3
2792 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .