3-(4-Bromo-phen-yl)cyclo-pent-2-en-1-one.

In the title compound, C11H9BrO, the cyclo-pentenone ring is almost planar with an r.m.s. deviation of 0.0097 Å. The largest inter-ring torsion angles [2.4 (3), 1.3 (3) and 3.53 (2)°] reveal only a very small twist between the rings, and suggest that the two rings are conjugated. The mol-ecule is slightly bowed, as shown by the small dihedral angle between the rings [5.3 (1)°]. The crystal packing pattern consists of parallel sheets that stack parallel to the ac plane. Each sheet consists of mol-ecules that pack side-to-side with the same relative orientation of phenyl and cyclo-pentenone rings along the a- and c-axis directions. Slipped side-to-side, face-to-face and edge-to-face inter-actions exist between pairs of sheets with edge-to-edge and edge-to-face O⋯H-C(sp (2)) weak hydrogen-bond contacts. A relatively short edge-to-face contact (2.77 Å) also exists between pairs of sheets.

Related literature

For structures of related 3-Ph substituted cyclo­pent-2-ene-1-ones, see: Zhao et al. (2008 ▶); Marjani et al. (2007 ▶, 2008 ▶); Jedrzejas et al. (1996 ▶). For leading references on the synthesis and uses of substituted cyclo­pentenones, see: Gibson et al. (2004 ▶); Gibson & Mainolfi (2005 ▶); Liu et al. (2013 ▶); Barluenga et al. (2012 ▶); Varea et al. (2012 ▶). For materials chemistry applications, see: Peloquin et al. (2012 ▶); Li et al. (2008 ▶). For the synthesis of the title compound, see: Heck (1965 ▶). For weak hydrogen bonds, see: Arunan et al. (2011 ▶).

Experimental

Crystal data

C11H9BrO

M = 237.09

Monoclinic,

a = 10.0219 (12) Å

b = 9.7818 (11) Å

c = 9.9945 (12) Å

β = 107.4375 (14)°

V = 934.76 (19) Å3

Z = 4

Mo Kα radiation

μ = 4.35 mm−1

T = 100 K

0.30 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan SADABS (Bruker, 2013 ▶) T min = 0.53, T max = 0.75

9994 measured reflections

2316 independent reflections

1917 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.057

S = 1.02

2316 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXP (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681401071X/mw2122sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401071X/mw2122Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401071X/mw2122Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401071X/mw2122Isup4.cml

CCDC reference: 999140

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H9BrO	Dx = 1.685 Mg m−3
Mr = 237.09	Melting point: 127.0 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0219 (12) Å	Cell parameters from 3089 reflections
b = 9.7818 (11) Å	θ = 3.0–28.6°
c = 9.9945 (12) Å	µ = 4.35 mm−1
β = 107.4375 (14)°	T = 100 K
V = 934.76 (19) Å3	Rectangular prism, colourless
Z = 4	0.30 × 0.13 × 0.07 mm
F(000) = 472

Bruker SMART APEX CCD diffractometer	2316 independent reflections
Radiation source: fine focus sealed tube	1917 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 2.1°
ω scans	h = −13→13
Absorption correction: multi-scan SADABS (Bruker, 2013)	k = −12→13
Tmin = 0.53, Tmax = 0.75	l = −13→13
9994 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0233P)2 + 0.4987P] where P = (Fo2 + 2Fc2)/3
2316 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
Br1	−0.30717 (2)	0.07926 (2)	0.08100 (2)	0.02888 (8)
O1	0.59890 (14)	0.08928 (13)	0.72449 (14)	0.0228 (3)
C1	0.4771 (2)	0.12867 (19)	0.68736 (19)	0.0181 (4)
C2	0.3642 (2)	0.07755 (19)	0.56825 (19)	0.0181 (4)
H2	0.3743	0.0067	0.507	0.022*
C3	0.2442 (2)	0.14462 (17)	0.55725 (18)	0.0154 (4)
C4	0.2622 (2)	0.24952 (19)	0.67199 (19)	0.0204 (4)
H4A	0.2025	0.2274	0.732	0.024*
H4B	0.2377	0.342	0.6319	0.024*
C5	0.4180 (2)	0.2416 (2)	0.7563 (2)	0.0229 (4)
H5A	0.4655	0.3295	0.7519	0.027*
H5B	0.4294	0.2194	0.8558	0.027*
C6	0.10968 (19)	0.12424 (18)	0.44782 (18)	0.0152 (4)
C7	0.0981 (2)	0.03111 (18)	0.33801 (19)	0.0177 (4)
H7	0.1767	−0.0228	0.3368	0.021*
C8	−0.0265 (2)	0.01702 (19)	0.23155 (19)	0.0198 (4)
H8	−0.0338	−0.0465	0.1578	0.024*
C9	−0.1403 (2)	0.09624 (19)	0.23345 (19)	0.0187 (4)
C10	−0.1341 (2)	0.18783 (19)	0.34090 (19)	0.0191 (4)
H10	−0.2135	0.2406	0.3416	0.023*
C11	−0.0086 (2)	0.20035 (18)	0.44772 (19)	0.0181 (4)
H11	−0.0029	0.2622	0.5225	0.022*

	U11	U22	U33	U12	U13	U23
Br1	0.02309 (12)	0.03472 (13)	0.02207 (11)	0.00371 (9)	−0.00349 (8)	−0.00033 (8)
O1	0.0171 (7)	0.0241 (7)	0.0251 (7)	0.0006 (5)	0.0031 (6)	−0.0043 (6)
C1	0.0187 (10)	0.0163 (8)	0.0192 (9)	−0.0016 (7)	0.0054 (8)	−0.0006 (7)
C2	0.0183 (10)	0.0187 (9)	0.0179 (9)	−0.0011 (7)	0.0063 (8)	−0.0043 (7)
C3	0.0189 (9)	0.0134 (8)	0.0157 (8)	−0.0017 (7)	0.0077 (7)	0.0018 (6)
C4	0.0223 (10)	0.0172 (9)	0.0218 (9)	0.0016 (7)	0.0068 (8)	−0.0031 (7)
C5	0.0239 (10)	0.0203 (9)	0.0226 (9)	0.0004 (8)	0.0039 (8)	−0.0071 (8)
C6	0.0168 (9)	0.0135 (8)	0.0159 (8)	−0.0017 (7)	0.0061 (7)	0.0033 (6)
C7	0.0169 (10)	0.0175 (8)	0.0202 (9)	0.0012 (7)	0.0078 (8)	0.0007 (7)
C8	0.0219 (10)	0.0197 (9)	0.0180 (9)	−0.0028 (7)	0.0063 (8)	−0.0013 (7)
C9	0.0167 (10)	0.0215 (9)	0.0161 (9)	−0.0004 (7)	0.0021 (7)	0.0053 (7)
C10	0.0181 (10)	0.0178 (9)	0.0222 (9)	0.0041 (7)	0.0073 (8)	0.0028 (7)
C11	0.0211 (10)	0.0166 (8)	0.0177 (9)	0.0011 (7)	0.0076 (8)	0.0009 (7)

Br1—C9	1.9022 (19)	C5—H5B	0.99
O1—C1	1.226 (2)	C6—C11	1.399 (3)
C1—C2	1.463 (3)	C6—C7	1.404 (3)
C1—C5	1.514 (3)	C7—C8	1.383 (3)
C2—C3	1.346 (3)	C7—H7	0.95
C2—H2	0.95	C8—C9	1.384 (3)
C3—C6	1.473 (3)	C8—H8	0.95
C3—C4	1.509 (2)	C9—C10	1.386 (3)
C4—C5	1.538 (3)	C10—C11	1.391 (3)
C4—H4A	0.99	C10—H10	0.95
C4—H4B	0.99	C11—H11	0.95
C5—H5A	0.99
O1—C1—C2	126.57 (17)	H5A—C5—H5B	108.8
O1—C1—C5	125.55 (17)	C11—C6—C7	118.25 (17)
C2—C1—C5	107.87 (16)	C11—C6—C3	120.99 (16)
C3—C2—C1	110.76 (16)	C7—C6—C3	120.72 (16)
C3—C2—H2	124.6	C8—C7—C6	120.64 (18)
C1—C2—H2	124.6	C8—C7—H7	119.7
C2—C3—C6	126.28 (17)	C6—C7—H7	119.7
C2—C3—C4	111.66 (16)	C7—C8—C9	119.44 (18)
C6—C3—C4	122.05 (16)	C7—C8—H8	120.3
C3—C4—C5	104.63 (15)	C9—C8—H8	120.3
C3—C4—H4A	110.8	C8—C9—C10	121.80 (18)
C5—C4—H4A	110.8	C8—C9—Br1	118.07 (14)
C3—C4—H4B	110.8	C10—C9—Br1	120.11 (14)
C5—C4—H4B	110.8	C9—C10—C11	118.16 (17)
H4A—C4—H4B	108.9	C9—C10—H10	120.9
C1—C5—C4	105.03 (15)	C11—C10—H10	120.9
C1—C5—H5A	110.7	C10—C11—C6	121.68 (17)
C4—C5—H5A	110.7	C10—C11—H11	119.2
C1—C5—H5B	110.7	C6—C11—H11	119.2
C4—C5—H5B	110.7
O1—C1—C2—C3	−179.48 (18)	C4—C3—C6—C7	176.47 (16)
C5—C1—C2—C3	−0.5 (2)	C11—C6—C7—C8	1.1 (3)
C1—C2—C3—C6	177.94 (16)	C3—C6—C7—C8	−176.78 (16)
C1—C2—C3—C4	−1.0 (2)	C6—C7—C8—C9	0.3 (3)
C2—C3—C4—C5	2.0 (2)	C7—C8—C9—C10	−1.3 (3)
C6—C3—C4—C5	−176.98 (16)	C7—C8—C9—Br1	177.38 (14)
O1—C1—C5—C4	−179.30 (18)	C8—C9—C10—C11	0.9 (3)
C2—C1—C5—C4	1.7 (2)	Br1—C9—C10—C11	−177.78 (13)
C3—C4—C5—C1	−2.16 (19)	C9—C10—C11—C6	0.5 (3)
C2—C3—C6—C11	179.84 (18)	C7—C6—C11—C10	−1.5 (3)
C4—C3—C6—C11	−1.3 (3)	C3—C6—C11—C10	176.34 (16)
C2—C3—C6—C7	−2.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.58	3.465 (2)	154
C7—H7···O1i	0.95	2.58	3.484 (3)	158
C10—H10···O1ii	0.95	2.52	3.377 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.58	3.465 (2)	154
C7—H7⋯O1i	0.95	2.58	3.484 (3)	158
C10—H10⋯O1ii	0.95	2.52	3.377 (2)	150

Symmetry codes: (i) ; (ii) .