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

In the title compound, C(16)H(11)BrO, the dihydro-indene ring system is approximately planar, with a maximum deviation of 0.008 (2) Å. The mean plane of this ring system forms a dihedral angle of 3.73 (11)°, with the bromo-substituted benzene ring. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into sheets parallel to the ab plane and further stabilization is provided by weak C-H⋯π inter-actions involving the bromo-substituted benzene rings.

Related literature

For background information on indanones, see: Schumann et al. (2001 ▶); Herzog et al. (2002 ▶); Sato (1999 ▶); Leoni et al. (2000 ▶); Sugimoto (1999 ▶); Beukes et al. (1998) ▶. For closely related structures, see: Ali et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C16H11BrO

M = 299.16

Monoclinic,

a = 6.1933 (7) Å

b = 4.7441 (5) Å

c = 21.8572 (19) Å

β = 99.108 (3)°

V = 634.10 (11) Å3

Z = 2

Mo Kα radiation

μ = 3.23 mm−1

T = 297 K

0.35 × 0.16 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.398, T max = 0.820

6671 measured reflections

2884 independent reflections

2314 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.057

S = 1.00

2884 reflections

164 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶) 1189 Friedel pairs

Flack parameter: 0.00 (6)

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/S1600536811031746/lh5300sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031746/lh5300Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031746/lh5300Isup3.cml

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

C16H11BrO	F(000) = 300
Mr = 299.16	Dx = 1.567 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2130 reflections
a = 6.1933 (7) Å	θ = 3.3–24.6°
b = 4.7441 (5) Å	µ = 3.23 mm−1
c = 21.8572 (19) Å	T = 297 K
β = 99.108 (3)°	Plate, colourless
V = 634.10 (11) Å3	0.35 × 0.16 × 0.06 mm
Z = 2

Bruker SMART APEXII DUO CCD area-detector diffractometer	2884 independent reflections
Radiation source: fine-focus sealed tube	2314 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 29.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.398, Tmax = 0.820	k = −6→6
6671 measured reflections	l = −29→29

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)] = 0.027	H-atom parameters constrained
wR(F2) = 0.057	w = 1/[σ2(Fo2) + (0.0281P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2884 reflections	Δρmax = 0.25 e Å−3
164 parameters	Δρmin = −0.15 e Å−3
2 restraints	Absolute structure: Flack (1983) 1189 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (6)

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
Br1	1.082380 (15)	1.59421 (5)	0.528270 (11)	0.06352 (10)
O1	0.1862 (3)	0.3615 (4)	0.29957 (9)	0.0621 (5)
C1	0.5691 (4)	1.0857 (5)	0.45115 (11)	0.0475 (6)
H1A	0.4363	1.0274	0.4617	0.057*
C2	0.6967 (4)	1.2730 (6)	0.48919 (11)	0.0508 (6)
H2A	0.6505	1.3426	0.5247	0.061*
C3	0.8943 (4)	1.3551 (5)	0.47354 (11)	0.0469 (5)
C4	0.9614 (4)	1.2637 (6)	0.41993 (11)	0.0478 (6)
H4A	1.0926	1.3275	0.4093	0.057*
C5	0.8327 (4)	1.0764 (6)	0.38194 (11)	0.0466 (6)
H5A	0.8784	1.0126	0.3458	0.056*
C6	0.6340 (4)	0.9814 (6)	0.39723 (11)	0.0409 (5)
C7	0.4929 (3)	0.7746 (6)	0.36006 (10)	0.0438 (5)
H7A	0.3638	0.7333	0.3749	0.053*
C8	0.5191 (4)	0.6371 (5)	0.30879 (11)	0.0399 (5)
C9	0.7021 (4)	0.6449 (5)	0.26989 (10)	0.0414 (6)
H9A	0.7175	0.8319	0.2532	0.050*
H9B	0.8403	0.5885	0.2941	0.050*
C10	0.6285 (4)	0.4365 (5)	0.21908 (12)	0.0415 (6)
C11	0.7351 (5)	0.3606 (6)	0.17000 (12)	0.0541 (6)
H11A	0.8682	0.4418	0.1654	0.065*
C12	0.6374 (5)	0.1604 (6)	0.12821 (13)	0.0635 (7)
H12A	0.7059	0.1078	0.0951	0.076*
C13	0.4405 (6)	0.0381 (7)	0.13496 (14)	0.0609 (7)
H13A	0.3791	−0.0966	0.1065	0.073*
C14	0.3334 (4)	0.1125 (6)	0.18326 (12)	0.0529 (6)
H14A	0.2006	0.0305	0.1879	0.063*
C15	0.4308 (4)	0.3145 (5)	0.22484 (10)	0.0445 (5)
C16	0.3531 (4)	0.4282 (5)	0.28031 (12)	0.0450 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.06614 (16)	0.06279 (16)	0.06060 (15)	−0.0043 (2)	0.00682 (10)	−0.00762 (18)
O1	0.0404 (9)	0.0778 (14)	0.0716 (12)	−0.0037 (9)	0.0194 (8)	−0.0069 (10)
C1	0.0478 (12)	0.0513 (15)	0.0479 (12)	0.0046 (13)	0.0210 (10)	0.0048 (12)
C2	0.0597 (15)	0.0527 (16)	0.0439 (12)	0.0045 (13)	0.0204 (11)	0.0013 (11)
C3	0.0507 (12)	0.0432 (14)	0.0467 (12)	0.0087 (11)	0.0078 (10)	0.0069 (10)
C4	0.0453 (12)	0.0522 (16)	0.0481 (12)	−0.0004 (12)	0.0138 (9)	0.0055 (12)
C5	0.0465 (12)	0.0543 (17)	0.0421 (12)	0.0031 (13)	0.0171 (9)	0.0028 (11)
C6	0.0414 (11)	0.0427 (12)	0.0402 (12)	0.0073 (11)	0.0116 (10)	0.0060 (11)
C7	0.0361 (10)	0.0533 (15)	0.0451 (12)	0.0051 (11)	0.0157 (9)	0.0090 (11)
C8	0.0346 (10)	0.0449 (14)	0.0417 (12)	0.0098 (10)	0.0109 (10)	0.0070 (10)
C9	0.0388 (12)	0.0442 (15)	0.0438 (12)	0.0063 (11)	0.0143 (10)	0.0058 (10)
C10	0.0450 (12)	0.0384 (14)	0.0425 (13)	0.0117 (11)	0.0111 (10)	0.0062 (10)
C11	0.0613 (14)	0.0538 (16)	0.0519 (13)	0.0039 (13)	0.0232 (12)	−0.0010 (12)
C12	0.083 (2)	0.0614 (18)	0.0494 (14)	0.0138 (16)	0.0208 (13)	−0.0018 (13)
C13	0.073 (2)	0.0552 (17)	0.0513 (16)	0.0106 (17)	−0.0003 (13)	−0.0036 (13)
C14	0.0481 (13)	0.0514 (16)	0.0558 (14)	0.0044 (13)	−0.0026 (11)	0.0017 (12)
C15	0.0435 (11)	0.0442 (13)	0.0455 (12)	0.0102 (11)	0.0065 (9)	0.0051 (10)
C16	0.0360 (12)	0.0512 (16)	0.0480 (13)	0.0111 (11)	0.0073 (10)	0.0076 (11)

Br1—C3	1.906 (3)	C8—C9	1.521 (3)
O1—C16	1.219 (3)	C9—C10	1.503 (4)
C1—C2	1.378 (4)	C9—H9A	0.9700
C1—C6	1.395 (3)	C9—H9B	0.9700
C1—H1A	0.9300	C10—C15	1.377 (4)
C2—C3	1.378 (4)	C10—C11	1.393 (4)
C2—H2A	0.9300	C11—C12	1.388 (4)
C3—C4	1.374 (3)	C11—H11A	0.9300
C4—C5	1.380 (4)	C12—C13	1.379 (5)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C6	1.400 (3)	C13—C14	1.378 (4)
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.470 (4)	C14—C15	1.391 (4)
C7—C8	1.329 (3)	C14—H14A	0.9300
C7—H7A	0.9300	C15—C16	1.476 (3)
C8—C16	1.491 (4)
C2—C1—C6	121.6 (2)	C8—C9—H9A	111.1
C2—C1—H1A	119.2	C10—C9—H9B	111.1
C6—C1—H1A	119.2	C8—C9—H9B	111.1
C1—C2—C3	118.7 (2)	H9A—C9—H9B	109.1
C1—C2—H2A	120.7	C15—C10—C11	119.9 (2)
C3—C2—H2A	120.7	C15—C10—C9	112.3 (2)
C4—C3—C2	121.5 (2)	C11—C10—C9	127.9 (2)
C4—C3—Br1	119.07 (19)	C12—C11—C10	118.2 (3)
C2—C3—Br1	119.40 (19)	C12—C11—H11A	120.9
C3—C4—C5	119.5 (2)	C10—C11—H11A	120.9
C3—C4—H4A	120.3	C13—C12—C11	121.2 (3)
C5—C4—H4A	120.3	C13—C12—H12A	119.4
C4—C5—C6	120.6 (2)	C11—C12—H12A	119.4
C4—C5—H5A	119.7	C14—C13—C12	121.0 (3)
C6—C5—H5A	119.7	C14—C13—H13A	119.5
C1—C6—C5	118.0 (2)	C12—C13—H13A	119.5
C1—C6—C7	118.6 (2)	C13—C14—C15	117.7 (3)
C5—C6—C7	123.4 (2)	C13—C14—H14A	121.1
C8—C7—C6	130.7 (2)	C15—C14—H14A	121.1
C8—C7—H7A	114.6	C10—C15—C14	122.0 (2)
C6—C7—H7A	114.6	C10—C15—C16	109.4 (2)
C7—C8—C16	120.7 (2)	C14—C15—C16	128.7 (2)
C7—C8—C9	131.4 (2)	O1—C16—C15	126.4 (2)
C16—C8—C9	108.0 (2)	O1—C16—C8	126.5 (2)
C10—C9—C8	103.4 (2)	C15—C16—C8	107.0 (2)
C10—C9—H9A	111.1
C6—C1—C2—C3	−0.8 (4)	C9—C10—C11—C12	179.6 (3)
C1—C2—C3—C4	2.7 (4)	C10—C11—C12—C13	−0.3 (4)
C1—C2—C3—Br1	−175.86 (18)	C11—C12—C13—C14	0.5 (5)
C2—C3—C4—C5	−2.6 (4)	C12—C13—C14—C15	−0.1 (4)
Br1—C3—C4—C5	175.93 (18)	C11—C10—C15—C14	0.8 (4)
C3—C4—C5—C6	0.7 (4)	C9—C10—C15—C14	−179.1 (2)
C2—C1—C6—C5	−1.1 (4)	C11—C10—C15—C16	179.7 (2)
C2—C1—C6—C7	177.9 (2)	C9—C10—C15—C16	−0.3 (3)
C4—C5—C6—C1	1.2 (4)	C13—C14—C15—C10	−0.6 (4)
C4—C5—C6—C7	−177.8 (2)	C13—C14—C15—C16	−179.2 (3)
C1—C6—C7—C8	−177.5 (3)	C10—C15—C16—O1	−178.5 (3)
C5—C6—C7—C8	1.5 (4)	C14—C15—C16—O1	0.3 (4)
C6—C7—C8—C16	178.2 (2)	C10—C15—C16—C8	0.7 (3)
C6—C7—C8—C9	−0.6 (5)	C14—C15—C16—C8	179.5 (2)
C7—C8—C9—C10	179.5 (3)	C7—C8—C16—O1	−0.7 (4)
C16—C8—C9—C10	0.7 (2)	C9—C8—C16—O1	178.3 (3)
C8—C9—C10—C15	−0.2 (3)	C7—C8—C16—C15	−179.8 (2)
C8—C9—C10—C11	179.8 (3)	C9—C8—C16—C15	−0.9 (2)
C15—C10—C11—C12	−0.4 (4)

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1i	0.93	2.56	3.199 (3)	126
C9—H9B···O1ii	0.97	2.38	3.256 (3)	149
C9—H9A···Cg1iii	0.97	2.68	3.528 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1i	0.93	2.56	3.199 (3)	126
C9—H9B⋯O1ii	0.97	2.38	3.256 (3)	149
C9—H9A⋯Cg1iii	0.97	2.68	3.528 (3)	147

Symmetry codes: (i) ; (ii) ; (iii) .