tert-Butyl 2-(4-chloro-benzo-yl)-2-methyl-propanoate.

The title compound, C(15)H(19)ClO(3), is bent with a dihedral angle of 72.02 (9)° between the mean planes of the benzene ring and a group encompassing the ester functionality (O=C-O-C). In the crystal, mol-ecules related by inversion symmetry are connected by weak C-H⋯O inter-actions into infinite chains. These inter-actions involve H atoms from a methyl group of the dimethyl residue and the O atoms of the ketone on one side of a mol-ecule; on the other side there are inter-actions between H atoms of the benzene ring and the carbonyl O atoms of the ester functionality. There are no directional inter-actions between the chains.

Related literature

For the synthesis, spectroscopic characterization and reactivity of the title compound, see: Logue (1974 ▶); Logue et al. (1975 ▶). For related structures, see: Crosse et al. (2010 ▶); Gould et al. (2010 ▶); Logue et al. (2010 ▶). For the syntheses and characterization of structurally similar indanone-derived β-keto ester derivatives, see: Mouri et al. (2009 ▶); Noritake et al. (2008 ▶); Rigby & Dixon (2008 ▶). For weak hydrogen-bonded inter­actions, see: Karle et al. (2009 ▶).

Experimental

Crystal data

C15H19ClO3

M = 282.75

Triclinic,

a = 8.601 (3) Å

b = 9.214 (2) Å

c = 11.033 (2) Å

α = 72.67 (2)°

β = 74.62 (2)°

γ = 74.02 (3)°

V = 786.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 291 K

0.30 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.905, T max = 0.929

2961 measured reflections

2759 independent reflections

1589 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 166 min intensity decay: 9%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.01

2759 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003156/zl2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003156/zl2267Isup2.hkl

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

C15H19ClO3	Z = 2
Mr = 282.75	F(000) = 300
Triclinic, P1	Dx = 1.194 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.601 (3) Å	Cell parameters from 25 reflections
b = 9.214 (2) Å	θ = 10–15°
c = 11.033 (2) Å	µ = 0.24 mm−1
α = 72.67 (2)°	T = 291 K
β = 74.62 (2)°	Prism, colourless
γ = 74.02 (3)°	0.30 × 0.30 × 0.30 mm
V = 786.3 (4) Å3

Enraf–Nonius TurboCAD-4 diffractometer	1589 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.020
graphite	θmax = 25.0°, θmin = 2.0°
non–profiled ω/2τ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.905, Tmax = 0.929	l = −12→13
2961 measured reflections	3 standard reflections every 166 min
2759 independent reflections	intensity decay: 9%

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.1997P] where P = (Fo2 + 2Fc2)/3
2759 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. Number of psi-scan sets used was 3. Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.16763 (12)	0.07087 (11)	0.34258 (10)	0.1148 (4)
C1	0.0088 (3)	0.2115 (3)	0.2795 (3)	0.0715 (8)
C2	0.0200 (4)	0.2567 (3)	0.1470 (3)	0.0732 (8)
H2	0.112	0.2139	0.0922	0.088*
C3	−0.1066 (3)	0.3656 (3)	0.0975 (3)	0.0652 (7)
H3	−0.0996	0.3952	0.0083	0.078*
C4	−0.2453 (3)	0.4331 (3)	0.1768 (2)	0.0539 (6)
C5	−0.2524 (3)	0.3851 (3)	0.3101 (2)	0.0616 (7)
H5	−0.3433	0.4288	0.3654	0.074*
C6	−0.1270 (4)	0.2740 (3)	0.3615 (3)	0.0733 (8)
H6	−0.1341	0.2417	0.4507	0.088*
C7	−0.3731 (3)	0.5568 (3)	0.1130 (2)	0.0567 (6)
O1	−0.3574 (2)	0.5870 (2)	−0.00407 (18)	0.0818 (6)
C8	−0.5234 (3)	0.6450 (3)	0.1932 (2)	0.0580 (7)
C9	−0.6140 (4)	0.7842 (4)	0.1003 (3)	0.0858 (9)
H9A	−0.6522	0.7464	0.0436	0.129*
H9B	−0.5396	0.8509	0.0499	0.129*
H9C	−0.7065	0.8416	0.1499	0.129*
C10	−0.6413 (3)	0.5359 (4)	0.2725 (3)	0.0815 (9)
H10A	−0.6754	0.4959	0.215	0.122*
H10B	−0.7364	0.5926	0.3205	0.122*
H10C	−0.5855	0.451	0.3316	0.122*
C11	−0.4693 (3)	0.7139 (3)	0.2811 (3)	0.0557 (6)
O2	−0.5376 (2)	0.7174 (2)	0.39021 (18)	0.0768 (6)
O3	−0.3370 (2)	0.77357 (18)	0.21611 (15)	0.0573 (5)
C12	−0.2559 (3)	0.8503 (3)	0.2752 (3)	0.0652 (7)
C13	−0.1158 (4)	0.8952 (4)	0.1653 (3)	0.0982 (11)
H13A	−0.1601	0.9655	0.0928	0.147*
H13B	−0.0465	0.8035	0.14	0.147*
H13C	−0.052	0.945	0.1934	0.147*
C14	−0.3741 (4)	0.9938 (4)	0.3095 (4)	0.1056 (12)
H14A	−0.4215	1.0563	0.2361	0.158*
H14B	−0.3158	1.053	0.3331	0.158*
H14C	−0.4602	0.9636	0.381	0.158*
C15	−0.1904 (5)	0.7350 (4)	0.3885 (3)	0.1139 (13)
H15A	−0.2809	0.7124	0.4587	0.171*
H15B	−0.1196	0.7781	0.4159	0.171*
H15C	−0.129	0.6409	0.3633	0.171*

	U11	U22	U33	U12	U13	U23
Cl1	0.0975 (7)	0.1088 (7)	0.1345 (8)	0.0243 (5)	−0.0444 (6)	−0.0478 (6)
C1	0.0677 (18)	0.0628 (18)	0.088 (2)	−0.0045 (14)	−0.0202 (16)	−0.0288 (16)
C2	0.0654 (18)	0.0720 (19)	0.080 (2)	−0.0162 (16)	0.0064 (16)	−0.0313 (16)
C3	0.0745 (19)	0.0649 (17)	0.0575 (16)	−0.0239 (15)	0.0015 (15)	−0.0214 (14)
C4	0.0614 (15)	0.0556 (15)	0.0498 (14)	−0.0241 (13)	−0.0005 (12)	−0.0191 (12)
C5	0.0671 (17)	0.0592 (16)	0.0559 (16)	−0.0098 (14)	−0.0034 (13)	−0.0213 (13)
C6	0.084 (2)	0.0683 (18)	0.0657 (17)	−0.0017 (16)	−0.0181 (16)	−0.0243 (15)
C7	0.0618 (17)	0.0631 (16)	0.0541 (16)	−0.0303 (14)	−0.0073 (13)	−0.0156 (13)
O1	0.0877 (14)	0.1077 (16)	0.0519 (12)	−0.0260 (12)	−0.0120 (10)	−0.0194 (11)
C8	0.0535 (15)	0.0655 (16)	0.0594 (15)	−0.0163 (13)	−0.0123 (12)	−0.0171 (13)
C9	0.081 (2)	0.093 (2)	0.090 (2)	−0.0075 (17)	−0.0387 (18)	−0.0230 (18)
C10	0.0607 (18)	0.104 (2)	0.090 (2)	−0.0384 (17)	0.0024 (15)	−0.0343 (18)
C11	0.0538 (15)	0.0572 (16)	0.0549 (16)	−0.0106 (13)	−0.0100 (13)	−0.0139 (12)
O2	0.0796 (13)	0.0971 (15)	0.0575 (12)	−0.0311 (11)	0.0045 (10)	−0.0289 (10)
O3	0.0587 (10)	0.0672 (11)	0.0543 (10)	−0.0232 (9)	−0.0074 (8)	−0.0217 (8)
C12	0.0684 (17)	0.0764 (18)	0.0660 (17)	−0.0271 (15)	−0.0107 (14)	−0.0314 (15)
C13	0.090 (2)	0.122 (3)	0.105 (3)	−0.058 (2)	0.0055 (19)	−0.049 (2)
C14	0.096 (3)	0.102 (3)	0.145 (3)	−0.026 (2)	−0.008 (2)	−0.077 (2)
C15	0.131 (3)	0.137 (3)	0.100 (3)	−0.054 (3)	−0.063 (2)	−0.009 (2)

Cl1—C1	1.739 (3)	C9—H9C	0.96
C1—C6	1.376 (4)	C10—H10A	0.96
C1—C2	1.380 (4)	C10—H10B	0.96
C2—C3	1.370 (4)	C10—H10C	0.96
C2—H2	0.93	C11—O2	1.197 (3)
C3—C4	1.392 (3)	C11—O3	1.337 (3)
C3—H3	0.93	O3—C12	1.483 (3)
C4—C5	1.394 (3)	C12—C15	1.504 (4)
C4—C7	1.498 (4)	C12—C14	1.509 (4)
C5—C6	1.380 (4)	C12—C13	1.515 (4)
C5—H5	0.93	C13—H13A	0.96
C6—H6	0.93	C13—H13B	0.96
C7—O1	1.216 (3)	C13—H13C	0.96
C7—C8	1.536 (3)	C14—H14A	0.96
C8—C11	1.526 (3)	C14—H14B	0.96
C8—C10	1.540 (4)	C14—H14C	0.96
C8—C9	1.546 (4)	C15—H15A	0.96
C9—H9A	0.96	C15—H15B	0.96
C9—H9B	0.96	C15—H15C	0.96
C6—C1—C2	120.9 (3)	C8—C10—H10B	109.5
C6—C1—Cl1	120.0 (2)	H10A—C10—H10B	109.5
C2—C1—Cl1	119.0 (2)	C8—C10—H10C	109.5
C3—C2—C1	119.0 (3)	H10A—C10—H10C	109.5
C3—C2—H2	120.5	H10B—C10—H10C	109.5
C1—C2—H2	120.5	O2—C11—O3	125.4 (2)
C2—C3—C4	122.0 (3)	O2—C11—C8	125.1 (2)
C2—C3—H3	119	O3—C11—C8	109.5 (2)
C4—C3—H3	119	C11—O3—C12	122.39 (19)
C3—C4—C5	117.5 (3)	O3—C12—C15	109.6 (2)
C3—C4—C7	117.9 (2)	O3—C12—C14	109.8 (2)
C5—C4—C7	124.5 (2)	C15—C12—C14	113.7 (3)
C6—C5—C4	121.1 (2)	O3—C12—C13	101.9 (2)
C6—C5—H5	119.4	C15—C12—C13	110.8 (3)
C4—C5—H5	119.4	C14—C12—C13	110.4 (3)
C1—C6—C5	119.4 (3)	C12—C13—H13A	109.5
C1—C6—H6	120.3	C12—C13—H13B	109.5
C5—C6—H6	120.3	H13A—C13—H13B	109.5
O1—C7—C4	119.2 (2)	C12—C13—H13C	109.5
O1—C7—C8	119.7 (2)	H13A—C13—H13C	109.5
C4—C7—C8	121.1 (2)	H13B—C13—H13C	109.5
C11—C8—C7	110.7 (2)	C12—C14—H14A	109.5
C11—C8—C10	111.1 (2)	C12—C14—H14B	109.5
C7—C8—C10	110.0 (2)	H14A—C14—H14B	109.5
C11—C8—C9	106.4 (2)	C12—C14—H14C	109.5
C7—C8—C9	109.0 (2)	H14A—C14—H14C	109.5
C10—C8—C9	109.7 (2)	H14B—C14—H14C	109.5
C8—C9—H9A	109.5	C12—C15—H15A	109.5
C8—C9—H9B	109.5	C12—C15—H15B	109.5
H9A—C9—H9B	109.5	H15A—C15—H15B	109.5
C8—C9—H9C	109.5	C12—C15—H15C	109.5
H9A—C9—H9C	109.5	H15A—C15—H15C	109.5
H9B—C9—H9C	109.5	H15B—C15—H15C	109.5
C8—C10—H10A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.96	2.58	3.476 (4)	155
C5—H5···O2ii	0.93	2.7	3.316 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.96	2.58	3.476 (4)	155
C5—H5⋯O2ii	0.93	2.7	3.316 (3)	125

Symmetry codes: (i) ; (ii) .