(E)-2-(4-Chloro-benzyl-idene)indan-1-one.

In the title compound, C(16)H(11)ClO, the dihedral angle between the almost planar dihydro-indene ring system (r.m.s. deviation = 0.009 Å) and the chloro-benzene ring is 3.51 (14)°. In the crystal, mol-ecules are connected by C-H⋯O and weak C-H⋯Cl inter-actions, forming infinite layers parallel to (101).

Related literature

For biological background to dihydro­indene derivatives, see: Akritopoulou-Zanze et al. (2007 ▶); Muhsin et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H11ClO

M = 254.70

Triclinic,

a = 3.8649 (2) Å

b = 6.5233 (3) Å

c = 12.1703 (6) Å

α = 91.374 (4)°

β = 95.914 (4)°

γ = 103.483 (4)°

V = 296.43 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.43 × 0.28 × 0.04 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.882, T max = 0.988

3942 measured reflections

2159 independent reflections

2072 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.06

2159 reflections

163 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.48 e Å−3

Absolute structure: Flack (1983 ▶), 870 Friedel pairs

Flack parameter: 0.05 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027589/hb5928sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027589/hb5928Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027589/hb5928Isup3.cml

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

C16H11ClO	Z = 1
Mr = 254.70	F(000) = 132
Triclinic, P1	Dx = 1.427 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8649 (2) Å	Cell parameters from 2756 reflections
b = 6.5233 (3) Å	θ = 3.2–32.1°
c = 12.1703 (6) Å	µ = 0.30 mm−1
α = 91.374 (4)°	T = 100 K
β = 95.914 (4)°	Plate, light-yellow
γ = 103.483 (4)°	0.43 × 0.28 × 0.04 mm
V = 296.43 (3) Å3

Bruker SMART APEXII CCD diffractometer	2159 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −4→4
Tmin = 0.882, Tmax = 0.988	k = −8→8
3942 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.1711P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2159 reflections	Δρmax = 0.63 e Å−3
163 parameters	Δρmin = −0.48 e Å−3
3 restraints	Absolute structure: Flack (1983), 870 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (8)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	1.33869 (16)	−0.02880 (10)	0.53352 (7)	0.0254 (2)
O1	0.9589 (7)	0.8574 (3)	0.0177 (2)	0.0249 (5)
C1	0.5969 (8)	0.2910 (5)	0.0183 (3)	0.0179 (7)
H1A	0.7420	0.1882	0.0046	0.022*
H1B	0.4062	0.2263	0.0639	0.022*
C2	0.4406 (9)	0.3621 (5)	−0.0892 (3)	0.0184 (6)
C3	0.2093 (9)	0.2374 (5)	−0.1742 (3)	0.0194 (7)
H3A	0.1294	0.0893	−0.1683	0.023*
C4	0.0999 (9)	0.3344 (5)	−0.2667 (3)	0.0226 (7)
H4A	−0.0572	0.2512	−0.3248	0.027*
C5	0.2154 (10)	0.5534 (6)	−0.2770 (3)	0.0239 (7)
H5A	0.1358	0.6175	−0.3410	0.029*
C6	0.4483 (9)	0.6754 (5)	−0.1921 (3)	0.0221 (7)
H6A	0.5322	0.8231	−0.1983	0.026*
C7	0.5554 (9)	0.5799 (5)	−0.0994 (3)	0.0196 (7)
C8	0.8022 (8)	0.6717 (5)	−0.0003 (3)	0.0186 (7)
C9	0.8293 (9)	0.4952 (5)	0.0738 (3)	0.0188 (7)
C10	1.0366 (9)	0.5332 (5)	0.1708 (3)	0.0195 (7)
H10A	1.1649	0.6758	0.1856	0.023*
C11	1.0966 (8)	0.3896 (5)	0.2575 (3)	0.0177 (7)
C12	1.3093 (9)	0.4750 (5)	0.3561 (3)	0.0205 (7)
H12A	1.4065	0.6231	0.3639	0.025*
C13	1.3816 (9)	0.3519 (6)	0.4415 (3)	0.0225 (7)
H13A	1.5242	0.4136	0.5076	0.027*
C14	1.2417 (9)	0.1354 (5)	0.4291 (3)	0.0202 (7)
C15	1.0307 (9)	0.0433 (5)	0.3330 (3)	0.0210 (7)
H15A	0.9361	−0.1051	0.3259	0.025*
C16	0.9595 (9)	0.1698 (5)	0.2477 (3)	0.0178 (7)
H16A	0.8164	0.1071	0.1818	0.021*

	U11	U22	U33	U12	U13	U23
Cl1	0.0283 (4)	0.0188 (4)	0.0279 (4)	0.0036 (3)	0.0010 (3)	0.0050 (3)
O1	0.0255 (13)	0.0120 (11)	0.0341 (13)	−0.0017 (10)	0.0027 (10)	0.0018 (9)
C1	0.0187 (16)	0.0079 (13)	0.0265 (16)	−0.0002 (12)	0.0066 (13)	0.0009 (11)
C2	0.0165 (16)	0.0129 (14)	0.0253 (15)	0.0011 (13)	0.0048 (12)	0.0038 (12)
C3	0.0150 (15)	0.0120 (15)	0.0273 (17)	−0.0045 (13)	0.0025 (13)	−0.0001 (12)
C4	0.0166 (16)	0.0209 (16)	0.0263 (16)	−0.0032 (14)	0.0017 (13)	−0.0013 (13)
C5	0.0201 (17)	0.0222 (18)	0.0279 (17)	0.0004 (14)	0.0046 (13)	0.0051 (13)
C6	0.0204 (17)	0.0136 (15)	0.0311 (18)	0.0006 (13)	0.0051 (14)	0.0042 (12)
C7	0.0161 (16)	0.0139 (15)	0.0272 (17)	−0.0006 (12)	0.0052 (13)	−0.0006 (12)
C8	0.0148 (15)	0.0118 (14)	0.0297 (17)	0.0024 (12)	0.0053 (13)	0.0037 (12)
C9	0.0163 (15)	0.0092 (15)	0.0293 (17)	−0.0019 (12)	0.0064 (13)	0.0006 (12)
C10	0.0180 (16)	0.0102 (14)	0.0276 (16)	−0.0023 (12)	0.0031 (13)	0.0005 (12)
C11	0.0146 (16)	0.0121 (15)	0.0262 (17)	0.0021 (12)	0.0040 (13)	0.0006 (12)
C12	0.0181 (16)	0.0131 (15)	0.0283 (17)	0.0003 (13)	0.0015 (13)	−0.0033 (12)
C13	0.0171 (17)	0.0207 (17)	0.0273 (18)	0.0001 (14)	0.0025 (14)	−0.0039 (14)
C14	0.0159 (17)	0.0200 (17)	0.0251 (17)	0.0037 (13)	0.0039 (13)	0.0088 (13)
C15	0.0209 (18)	0.0147 (16)	0.0270 (18)	0.0031 (14)	0.0030 (14)	0.0017 (13)
C16	0.0165 (16)	0.0111 (15)	0.0232 (17)	−0.0012 (13)	0.0014 (13)	0.0000 (12)

Cl1—C14	1.749 (3)	C7—C8	1.478 (5)
O1—C8	1.225 (4)	C8—C9	1.495 (4)
C1—C2	1.513 (5)	C9—C10	1.340 (5)
C1—C9	1.520 (4)	C10—C11	1.464 (5)
C1—H1A	0.9900	C10—H10A	0.9500
C1—H1B	0.9900	C11—C12	1.405 (4)
C2—C7	1.399 (4)	C11—C16	1.406 (4)
C2—C3	1.400 (4)	C12—C13	1.375 (5)
C3—C4	1.382 (5)	C12—H12A	0.9500
C3—H3A	0.9500	C13—C14	1.388 (5)
C4—C5	1.407 (5)	C13—H13A	0.9500
C4—H4A	0.9500	C14—C15	1.391 (5)
C5—C6	1.395 (5)	C15—C16	1.386 (5)
C5—H5A	0.9500	C15—H15A	0.9500
C6—C7	1.375 (5)	C16—H16A	0.9500
C6—H6A	0.9500
C2—C1—C9	103.1 (3)	C7—C8—C9	107.3 (3)
C2—C1—H1A	111.2	C10—C9—C8	120.3 (3)
C9—C1—H1A	111.2	C10—C9—C1	131.1 (3)
C2—C1—H1B	111.2	C8—C9—C1	108.5 (3)
C9—C1—H1B	111.2	C9—C10—C11	130.2 (3)
H1A—C1—H1B	109.1	C9—C10—H10A	114.9
C7—C2—C3	119.8 (3)	C11—C10—H10A	114.9
C7—C2—C1	112.3 (3)	C12—C11—C16	117.6 (3)
C3—C2—C1	127.8 (3)	C12—C11—C10	118.4 (3)
C4—C3—C2	118.6 (3)	C16—C11—C10	124.0 (3)
C4—C3—H3A	120.7	C13—C12—C11	122.4 (3)
C2—C3—H3A	120.7	C13—C12—H12A	118.8
C3—C4—C5	121.6 (3)	C11—C12—H12A	118.8
C3—C4—H4A	119.2	C12—C13—C14	118.5 (3)
C5—C4—H4A	119.2	C12—C13—H13A	120.8
C6—C5—C4	119.2 (3)	C14—C13—H13A	120.8
C6—C5—H5A	120.4	C13—C14—C15	121.3 (3)
C4—C5—H5A	120.4	C13—C14—Cl1	120.2 (2)
C7—C6—C5	119.4 (3)	C15—C14—Cl1	118.5 (3)
C7—C6—H6A	120.3	C16—C15—C14	119.5 (3)
C5—C6—H6A	120.3	C16—C15—H15A	120.3
C6—C7—C2	121.3 (3)	C14—C15—H15A	120.3
C6—C7—C8	129.9 (3)	C15—C16—C11	120.7 (3)
C2—C7—C8	108.7 (3)	C15—C16—H16A	119.6
O1—C8—C7	126.5 (3)	C11—C16—H16A	119.6
O1—C8—C9	126.1 (3)
C9—C1—C2—C7	−0.5 (4)	O1—C8—C9—C1	−178.8 (3)
C9—C1—C2—C3	178.9 (3)	C7—C8—C9—C1	0.6 (3)
C7—C2—C3—C4	0.0 (5)	C2—C1—C9—C10	−179.6 (3)
C1—C2—C3—C4	−179.4 (3)	C2—C1—C9—C8	−0.1 (3)
C2—C3—C4—C5	0.0 (5)	C8—C9—C10—C11	177.9 (3)
C3—C4—C5—C6	0.5 (5)	C1—C9—C10—C11	−2.6 (6)
C4—C5—C6—C7	−1.1 (5)	C9—C10—C11—C12	−175.1 (3)
C5—C6—C7—C2	1.2 (5)	C9—C10—C11—C16	6.1 (6)
C5—C6—C7—C8	178.7 (3)	C16—C11—C12—C13	−0.7 (5)
C3—C2—C7—C6	−0.6 (5)	C10—C11—C12—C13	−179.6 (3)
C1—C2—C7—C6	178.9 (3)	C11—C12—C13—C14	0.7 (5)
C3—C2—C7—C8	−178.6 (3)	C12—C13—C14—C15	−0.4 (5)
C1—C2—C7—C8	0.9 (4)	C12—C13—C14—Cl1	177.8 (3)
C6—C7—C8—O1	0.7 (5)	C13—C14—C15—C16	0.3 (5)
C2—C7—C8—O1	178.5 (3)	Cl1—C14—C15—C16	−178.0 (3)
C6—C7—C8—C9	−178.6 (3)	C14—C15—C16—C11	−0.3 (5)
C2—C7—C8—C9	−0.9 (4)	C12—C11—C16—C15	0.5 (5)
O1—C8—C9—C10	0.8 (5)	C10—C11—C16—C15	179.3 (3)
C7—C8—C9—C10	−179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.99	2.49	3.436 (4)	159
C5—H5A···Cl1ii	0.95	2.80	3.591 (4)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.99	2.49	3.436 (4)	159
C5—H5A⋯Cl1ii	0.95	2.80	3.591 (4)	141

Symmetry codes: (i) ; (ii) .