1-(4-Chloro-phen-yl)-4,4-dimethyl-pent-1-en-3-one.

In the title compound, C(13)H(15)ClO, the carbonyl and ethenyl groups are not coplanar with benzene ring system, forming dihedral angles of 35.37 (5) and 36.27 (11)°, respectively. The mol-ecules are packed in an offset face-to-face arrangement showing π-π stacking inter-actions involving the benzene rings [centroid-centroid distance = 3.586 (4) Å].

Related literature

The title compound is an important inter­mediate in the pesticide industry, see: Wang et al. (2006 ▶). For related structures, see: Anuradha et al. (2008 ▶); Butcher et al. (2007 ▶); Gong et al. (2008 ▶); Harrison et al. (2007 ▶); Patil et al. (2007 ▶); Sarojini et al. (2007 ▶); Thiruvalluvar et al. (2007 ▶); Thiruvalluvar et al. (2008 ▶); Xia & Hu (2008 ▶).

Experimental

Crystal data

C13H15ClO

M = 222.70

Triclinic,

a = 5.6831 (4) Å

b = 9.9156 (6) Å

c = 11.3731 (7) Å

α = 103.487 (1)°

β = 101.160 (1)°

γ = 103.697 (1)°

V = 584.12 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 173 (2) K

0.46 × 0.31 × 0.21 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.875, T max = 0.940

4545 measured reflections

2251 independent reflections

1989 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.094

S = 1.07

2251 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004358/pv2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004358/pv2132Isup2.hkl

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

C13H15ClO	Z = 2
Mr = 222.70	F(000) = 236
Triclinic, P1	Dx = 1.266 Mg m−3
Hall symbol: -P 1	Melting point: 360 K
a = 5.6831 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9156 (6) Å	Cell parameters from 3394 reflections
c = 11.3731 (7) Å	θ = 2.2–27.0°
α = 103.487 (1)°	µ = 0.30 mm−1
β = 101.160 (1)°	T = 173 K
γ = 103.697 (1)°	Block, colorless
V = 584.12 (7) Å3	0.46 × 0.31 × 0.21 mm

Bruker SMART 1000 CCD diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	1989 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→7
Tmin = 0.875, Tmax = 0.940	k = −12→11
4545 measured reflections	l = −13→13

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.1538P] where P = (Fo2 + 2Fc2)/3
2251 reflections	(Δ/σ)max = 0.001
139 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. 1H NMR(400MHz, CDCl3),delta:1.23(s, 9H, 3×CH3),7.09(d, J= 1.52Hz, 1H, 2-CH), 7.36(d, J=8.4Hz, 2H, benzene 3,5-H), 7.5(d, J= 8.4Hz, 2H, benzene 2,6-H), 7.60(d,J=15.6Hz, 1H, 1-CH).

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.

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 > σ(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	1.79614 (7)	1.22580 (4)	1.45960 (3)	0.03998 (15)
C1	0.8701 (3)	0.81783 (15)	1.07764 (13)	0.0281 (3)
H1	0.7164	0.8160	1.0994	0.034*
C2	0.8553 (3)	0.73017 (15)	0.96684 (13)	0.0292 (3)
H2	1.0047	0.7274	0.9420	0.035*
C3	0.6090 (3)	0.63638 (15)	0.88112 (13)	0.0274 (3)
C4	0.6118 (3)	0.51705 (15)	0.76919 (13)	0.0275 (3)
C5	0.3442 (3)	0.43184 (18)	0.69238 (15)	0.0415 (4)
H5A	0.2516	0.3883	0.7452	0.062*
H5B	0.3480	0.3550	0.6213	0.062*
H5C	0.2609	0.4974	0.6612	0.062*
C6	0.7443 (3)	0.41555 (16)	0.81908 (14)	0.0347 (3)
H6A	0.6574	0.3762	0.8757	0.052*
H6B	0.9188	0.4701	0.8647	0.052*
H6C	0.7412	0.3357	0.7487	0.052*
C7	0.7574 (3)	0.58705 (17)	0.68748 (14)	0.0361 (3)
H7A	0.7492	0.5121	0.6122	0.054*
H7B	0.9330	0.6345	0.7350	0.054*
H7C	0.6827	0.6593	0.6631	0.054*
C8	1.0991 (3)	0.91697 (14)	1.16967 (13)	0.0273 (3)
C9	1.3206 (3)	0.96763 (15)	1.13599 (13)	0.0310 (3)
H9	1.3244	0.9365	1.0510	0.037*
C10	1.5339 (3)	1.06235 (16)	1.22452 (14)	0.0316 (3)
H10	1.6825	1.0972	1.2005	0.038*
C11	1.5282 (3)	1.10569 (14)	1.34851 (13)	0.0291 (3)
C12	1.3137 (3)	1.05773 (16)	1.38509 (14)	0.0328 (3)
H12	1.3126	1.0879	1.4706	0.039*
C13	1.0999 (3)	0.96487 (15)	1.29538 (14)	0.0312 (3)
H13	0.9506	0.9331	1.3199	0.037*
O1	0.41421 (19)	0.65539 (12)	0.90060 (10)	0.0373 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0345 (2)	0.0357 (2)	0.0361 (2)	0.00107 (16)	0.00176 (15)	0.00061 (16)
C1	0.0257 (7)	0.0273 (7)	0.0319 (7)	0.0092 (5)	0.0075 (6)	0.0087 (6)
C2	0.0238 (7)	0.0309 (7)	0.0321 (7)	0.0091 (6)	0.0080 (5)	0.0063 (6)
C3	0.0254 (7)	0.0293 (7)	0.0287 (7)	0.0088 (6)	0.0075 (5)	0.0093 (6)
C4	0.0246 (7)	0.0287 (7)	0.0271 (7)	0.0079 (5)	0.0056 (5)	0.0053 (6)
C5	0.0286 (8)	0.0434 (9)	0.0394 (8)	0.0077 (7)	0.0024 (6)	−0.0039 (7)
C6	0.0376 (8)	0.0324 (8)	0.0378 (8)	0.0137 (6)	0.0122 (6)	0.0121 (6)
C7	0.0434 (9)	0.0384 (8)	0.0333 (8)	0.0166 (7)	0.0163 (7)	0.0134 (6)
C8	0.0289 (7)	0.0237 (7)	0.0299 (7)	0.0106 (6)	0.0065 (5)	0.0071 (5)
C9	0.0318 (8)	0.0323 (7)	0.0277 (7)	0.0087 (6)	0.0085 (6)	0.0068 (6)
C10	0.0272 (7)	0.0324 (7)	0.0342 (8)	0.0067 (6)	0.0087 (6)	0.0097 (6)
C11	0.0283 (7)	0.0219 (6)	0.0320 (7)	0.0065 (5)	0.0024 (6)	0.0039 (5)
C12	0.0360 (8)	0.0310 (7)	0.0284 (7)	0.0095 (6)	0.0081 (6)	0.0039 (6)
C13	0.0286 (7)	0.0312 (7)	0.0333 (7)	0.0081 (6)	0.0112 (6)	0.0067 (6)
O1	0.0247 (5)	0.0442 (6)	0.0382 (6)	0.0109 (5)	0.0093 (4)	0.0016 (5)

Cl1—C11	1.7401 (15)	C6—H6B	0.9800
C1—C2	1.328 (2)	C6—H6C	0.9800
C1—C8	1.464 (2)	C7—H7A	0.9800
C1—H1	0.9500	C7—H7B	0.9800
C2—C3	1.4855 (19)	C7—H7C	0.9800
C2—H2	0.9500	C8—C13	1.396 (2)
C3—O1	1.2185 (17)	C8—C9	1.400 (2)
C3—C4	1.5281 (19)	C9—C10	1.383 (2)
C4—C5	1.5242 (19)	C9—H9	0.9500
C4—C7	1.535 (2)	C10—C11	1.384 (2)
C4—C6	1.5368 (19)	C10—H10	0.9500
C5—H5A	0.9800	C11—C12	1.378 (2)
C5—H5B	0.9800	C12—C13	1.385 (2)
C5—H5C	0.9800	C12—H12	0.9500
C6—H6A	0.9800	C13—H13	0.9500
C2—C1—C8	126.64 (13)	H6B—C6—H6C	109.5
C2—C1—H1	116.7	C4—C7—H7A	109.5
C8—C1—H1	116.7	C4—C7—H7B	109.5
C1—C2—C3	121.13 (13)	H7A—C7—H7B	109.5
C1—C2—H2	119.4	C4—C7—H7C	109.5
C3—C2—H2	119.4	H7A—C7—H7C	109.5
O1—C3—C2	120.51 (13)	H7B—C7—H7C	109.5
O1—C3—C4	122.12 (13)	C13—C8—C9	118.03 (13)
C2—C3—C4	117.37 (12)	C13—C8—C1	119.85 (13)
C5—C4—C3	110.10 (12)	C9—C8—C1	122.13 (13)
C5—C4—C7	109.81 (12)	C10—C9—C8	121.03 (13)
C3—C4—C7	108.91 (11)	C10—C9—H9	119.5
C5—C4—C6	110.00 (12)	C8—C9—H9	119.5
C3—C4—C6	108.29 (11)	C9—C10—C11	119.20 (13)
C7—C4—C6	109.71 (12)	C9—C10—H10	120.4
C4—C5—H5A	109.5	C11—C10—H10	120.4
C4—C5—H5B	109.5	C12—C11—C10	121.34 (13)
H5A—C5—H5B	109.5	C12—C11—Cl1	119.52 (11)
C4—C5—H5C	109.5	C10—C11—Cl1	119.13 (11)
H5A—C5—H5C	109.5	C11—C12—C13	119.01 (13)
H5B—C5—H5C	109.5	C11—C12—H12	120.5
C4—C6—H6A	109.5	C13—C12—H12	120.5
C4—C6—H6B	109.5	C12—C13—C8	121.37 (13)
H6A—C6—H6B	109.5	C12—C13—H13	119.3
C4—C6—H6C	109.5	C8—C13—H13	119.3
H6A—C6—H6C	109.5
C8—C1—C2—C3	−178.96 (13)	C13—C8—C9—C10	0.0 (2)
C1—C2—C3—O1	12.6 (2)	C1—C8—C9—C10	179.39 (13)
C1—C2—C3—C4	−167.46 (13)	C8—C9—C10—C11	0.9 (2)
O1—C3—C4—C5	−0.29 (19)	C9—C10—C11—C12	−0.8 (2)
C2—C3—C4—C5	179.76 (12)	C9—C10—C11—Cl1	−179.58 (11)
O1—C3—C4—C7	120.17 (15)	C10—C11—C12—C13	−0.3 (2)
C2—C3—C4—C7	−59.79 (16)	Cl1—C11—C12—C13	178.49 (11)
O1—C3—C4—C6	−120.59 (15)	C11—C12—C13—C8	1.3 (2)
C2—C3—C4—C6	59.46 (16)	C9—C8—C13—C12	−1.1 (2)
C2—C1—C8—C13	−158.39 (14)	C1—C8—C13—C12	179.47 (13)
C2—C1—C8—C9	22.2 (2)