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

The title compound, C(16)H(22)O(3), is bent with a dihedral angle of 75.3 (1)° between the mean planes of the benzene ring and a group encompassing the ester functionality (O=C-O-C). In the crystal, the mol-ecules are linked into infinite chains held together by weak C-H⋯O hydrogen-bonded inter-actions between an H atom on the benzene ring of one mol-ecule and an O atom on the ketone functionality of an adjacent mol-ecule. The chains are arranged with neighbouring tert-butyl and dimethyl groups on adjacent chains exhibiting hydro-phobic stacking, with short C-H⋯H-C contacts (2.37 Å) between adjacent 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. (2010a ▶,b ▶; 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 ▶). For H⋯H inter­actions, see: Alkorta et al. (2008 ▶).

Experimental

Crystal data

C16H22O3

M = 262.34

Orthorhombic,

a = 8.605 (3) Å

b = 11.659 (3) Å

c = 31.347 (9) Å

V = 3144.9 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.50 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.969, T max = 0.988

4411 measured reflections

2758 independent reflections

1334 reflections with I > 2σ(I)

R int = 0.027

3 standard reflections every 166 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.134

S = 1.01

2758 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 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/S1600536810003144/zl2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003144/zl2266Isup2.hkl

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

C16H22O3	F(000) = 1136
Mr = 262.34	Dx = 1.108 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 8.605 (3) Å	θ = 10–15°
b = 11.659 (3) Å	µ = 0.08 mm−1
c = 31.347 (9) Å	T = 291 K
V = 3144.9 (16) Å3	Prism, colourless
Z = 8	0.50 × 0.30 × 0.10 mm

Enraf–Nonius TurboCAD-4 diffractometer	1334 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.027
graphite	θmax = 25.0°, θmin = 1.3°
non–profiled ω scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
Tmin = 0.969, Tmax = 0.988	l = −33→37
4411 measured reflections	3 standard reflections every 166 min
2758 independent reflections	intensity decay: 2%

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.2581P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2758 reflections	Δρmax = 0.14 e Å−3
178 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (5)

Experimental. Number of psi-scan sets used was 6. 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
C1	0.6338 (3)	0.2128 (2)	0.65195 (7)	0.0474 (6)
C2	0.7278 (3)	0.3098 (2)	0.65125 (7)	0.0558 (7)
H2	0.7806	0.3292	0.6264	0.067*
C3	0.7434 (3)	0.3773 (2)	0.68702 (8)	0.0647 (8)
H3	0.8068	0.4417	0.6857	0.078*
C4	0.6681 (4)	0.3524 (3)	0.72464 (9)	0.0701 (8)
C5	0.5731 (4)	0.2569 (3)	0.72513 (9)	0.0789 (9)
H5	0.5193	0.2385	0.7499	0.095*
C6	0.5566 (3)	0.1886 (2)	0.68967 (8)	0.0655 (8)
H6	0.4922	0.1247	0.691	0.079*
C7	0.6872 (5)	0.4275 (3)	0.76352 (9)	0.1102 (13)
H7A	0.5982	0.419	0.7817	0.165*
H7B	0.6963	0.5062	0.7548	0.165*
H7C	0.7791	0.4052	0.7787	0.165*
C8	0.6120 (3)	0.1326 (2)	0.61524 (8)	0.0517 (7)
O9	0.5392 (2)	0.04387 (16)	0.62062 (6)	0.0725 (6)
C10	0.6724 (3)	0.1633 (2)	0.57086 (8)	0.0527 (7)
C11	0.5841 (3)	0.2689 (2)	0.55401 (8)	0.0724 (9)
H111	0.5999	0.3323	0.573	0.109*
H112	0.4752	0.2516	0.5524	0.109*
H113	0.6221	0.2884	0.5262	0.109*
O12	0.9115 (2)	0.25100 (18)	0.54691 (6)	0.0790 (6)
O13	0.91700 (19)	0.11790 (14)	0.59947 (5)	0.0560 (5)
C14	0.6468 (4)	0.0623 (3)	0.54016 (8)	0.0826 (9)
H14A	0.6857	0.082	0.5124	0.124*
H14B	0.5378	0.0456	0.5383	0.124*
H14C	0.701	−0.004	0.5506	0.124*
C15	0.8467 (3)	0.1858 (2)	0.57099 (8)	0.0557 (7)
C16	1.0892 (3)	0.1174 (2)	0.60458 (8)	0.0608 (7)
C17	1.1112 (4)	0.0345 (3)	0.64115 (10)	0.1023 (12)
H17A	1.0663	−0.0383	0.6338	0.153*
H17B	1.0611	0.0641	0.6662	0.153*
H17C	1.2202	0.0249	0.6467	0.153*
C18	1.1633 (4)	0.0715 (3)	0.56456 (10)	0.0879 (10)
H181	1.2716	0.0574	0.5697	0.132*
H182	1.1522	0.1266	0.542	0.132*
H183	1.1132	0.0011	0.5565	0.132*
C19	1.1454 (4)	0.2360 (3)	0.61636 (11)	0.0997 (11)
H19A	1.0827	0.2658	0.6392	0.15*
H19B	1.1372	0.2856	0.592	0.15*
H19C	1.2518	0.2321	0.6254	0.15*

	U11	U22	U33	U12	U13	U23
C1	0.0430 (15)	0.0492 (15)	0.0498 (14)	0.0041 (13)	0.0019 (12)	0.0026 (12)
C2	0.0596 (18)	0.0602 (16)	0.0476 (14)	−0.0026 (15)	0.0060 (14)	0.0001 (13)
C3	0.0670 (19)	0.0641 (17)	0.0630 (16)	−0.0065 (16)	−0.0012 (17)	−0.0118 (14)
C4	0.076 (2)	0.077 (2)	0.0570 (18)	0.0119 (18)	−0.0004 (16)	−0.0141 (16)
C5	0.093 (2)	0.091 (2)	0.0528 (16)	0.003 (2)	0.0254 (17)	−0.0023 (17)
C6	0.0686 (19)	0.0664 (18)	0.0615 (17)	−0.0029 (16)	0.0132 (15)	0.0052 (15)
C7	0.130 (3)	0.124 (3)	0.077 (2)	0.007 (3)	0.006 (2)	−0.043 (2)
C8	0.0408 (17)	0.0548 (16)	0.0596 (16)	0.0055 (14)	−0.0066 (12)	0.0018 (14)
O9	0.0761 (15)	0.0639 (12)	0.0774 (12)	−0.0182 (11)	−0.0017 (11)	−0.0012 (10)
C10	0.0520 (17)	0.0610 (17)	0.0451 (14)	0.0039 (14)	−0.0048 (13)	−0.0042 (13)
C11	0.069 (2)	0.088 (2)	0.0601 (17)	0.0141 (17)	−0.0107 (15)	0.0107 (15)
O12	0.0748 (14)	0.0883 (14)	0.0741 (12)	0.0026 (12)	0.0128 (11)	0.0238 (12)
O13	0.0419 (11)	0.0711 (12)	0.0551 (10)	0.0015 (9)	−0.0019 (9)	0.0054 (9)
C14	0.077 (2)	0.096 (2)	0.074 (2)	−0.0039 (19)	−0.0078 (16)	−0.0319 (17)
C15	0.0585 (19)	0.0615 (17)	0.0471 (15)	0.0036 (16)	0.0019 (15)	−0.0046 (15)
C16	0.0424 (17)	0.0749 (19)	0.0651 (17)	−0.0023 (15)	−0.0056 (13)	0.0028 (15)
C17	0.067 (2)	0.139 (3)	0.101 (2)	0.002 (2)	−0.0184 (19)	0.042 (2)
C18	0.062 (2)	0.113 (3)	0.089 (2)	0.013 (2)	0.0140 (17)	−0.005 (2)
C19	0.068 (2)	0.103 (3)	0.128 (3)	−0.013 (2)	−0.017 (2)	−0.022 (2)

C1—C6	1.385 (3)	C11—H112	0.96
C1—C2	1.390 (3)	C11—H113	0.96
C1—C8	1.495 (3)	O12—C15	1.207 (3)
C2—C3	1.376 (3)	O13—C15	1.338 (3)
C2—H2	0.93	O13—C16	1.491 (3)
C3—C4	1.376 (4)	C14—H14A	0.96
C3—H3	0.93	C14—H14B	0.96
C4—C5	1.382 (4)	C14—H14C	0.96
C4—C7	1.509 (4)	C16—C18	1.505 (4)
C5—C6	1.375 (4)	C16—C19	1.511 (4)
C5—H5	0.93	C16—C17	1.511 (4)
C6—H6	0.93	C17—H17A	0.96
C7—H7A	0.96	C17—H17B	0.96
C7—H7B	0.96	C17—H17C	0.96
C7—H7C	0.96	C18—H181	0.96
C8—O9	1.221 (3)	C18—H182	0.96
C8—C10	1.528 (3)	C18—H183	0.96
C10—C15	1.523 (4)	C19—H19A	0.96
C10—C14	1.537 (3)	C19—H19B	0.96
C10—C11	1.540 (3)	C19—H19C	0.96
C11—H111	0.96
C6—C1—C2	117.3 (2)	H111—C11—H113	109.5
C6—C1—C8	118.0 (2)	H112—C11—H113	109.5
C2—C1—C8	124.7 (2)	C15—O13—C16	121.6 (2)
C3—C2—C1	120.6 (2)	C10—C14—H14A	109.5
C3—C2—H2	119.7	C10—C14—H14B	109.5
C1—C2—H2	119.7	H14A—C14—H14B	109.5
C4—C3—C2	122.2 (3)	C10—C14—H14C	109.5
C4—C3—H3	118.9	H14A—C14—H14C	109.5
C2—C3—H3	118.9	H14B—C14—H14C	109.5
C3—C4—C5	117.2 (3)	O12—C15—O13	125.5 (3)
C3—C4—C7	121.2 (3)	O12—C15—C10	124.2 (3)
C5—C4—C7	121.5 (3)	O13—C15—C10	110.2 (2)
C6—C5—C4	121.3 (3)	O13—C16—C18	109.4 (2)
C6—C5—H5	119.4	O13—C16—C19	109.9 (2)
C4—C5—H5	119.4	C18—C16—C19	113.2 (3)
C5—C6—C1	121.5 (3)	O13—C16—C17	102.0 (2)
C5—C6—H6	119.3	C18—C16—C17	110.6 (3)
C1—C6—H6	119.3	C19—C16—C17	111.1 (3)
C4—C7—H7A	109.5	C16—C17—H17A	109.5
C4—C7—H7B	109.5	C16—C17—H17B	109.5
H7A—C7—H7B	109.5	H17A—C17—H17B	109.5
C4—C7—H7C	109.5	C16—C17—H17C	109.5
H7A—C7—H7C	109.5	H17A—C17—H17C	109.5
H7B—C7—H7C	109.5	H17B—C17—H17C	109.5
O9—C8—C1	119.2 (2)	C16—C18—H181	109.5
O9—C8—C10	119.9 (2)	C16—C18—H182	109.5
C1—C8—C10	120.8 (2)	H181—C18—H182	109.5
C15—C10—C8	111.9 (2)	C16—C18—H183	109.5
C15—C10—C14	106.0 (2)	H181—C18—H183	109.5
C8—C10—C14	110.0 (2)	H182—C18—H183	109.5
C15—C10—C11	110.4 (2)	C16—C19—H19A	109.5
C8—C10—C11	109.4 (2)	C16—C19—H19B	109.5
C14—C10—C11	109.1 (2)	H19A—C19—H19B	109.5
C10—C11—H111	109.5	C16—C19—H19C	109.5
C10—C11—H112	109.5	H19A—C19—H19C	109.5
H111—C11—H112	109.5	H19B—C19—H19C	109.5
C10—C11—H113	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O9i	0.93	2.71	3.407 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O9i	0.93	2.71	3.407 (3)	133

Symmetry code: (i) .