tert-Butyl 2-benzoyl-2-methyl-propanoate.

The title compound, C(15)H(20)O(3), is bent with a dihedral angle of 67.28 (9)° between the mean planes of the phenyl 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. On one side of the mol-ecule there are two adjacent inter-actions between neighbouring mol-ecules involving the H atoms of methyl groups from the dimethyl groups and the O atoms of the ketone; on the other side, there are also two inter-actions to another adjacent mol-ecule involving the H atoms on the phenyl rings and the carbonyl O atoms of the ester functionality.

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 ▶); Gould 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

C15H20O3

M = 248.31

Triclinic,

a = 8.616 (3) Å

b = 8.696 (3) Å

c = 11.310 (5) Å

α = 73.25 (4)°

β = 72.25 (3)°

γ = 66.05 (3)°

V = 724.3 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.40 × 0.35 × 0.30 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.965, T max = 0.979

2735 measured reflections

2548 independent reflections

1689 reflections with I > 2σ(I)

R int = 0.015

3 standard reflections every 166 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.02

2548 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.12 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/S1600536810003120/zl2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003120/zl2265Isup2.hkl

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

C15H20O3	Z = 2
Mr = 248.31	F(000) = 268
Triclinic, P1	Dx = 1.139 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.616 (3) Å	Cell parameters from 25 reflections
b = 8.696 (3) Å	θ = 10–15°
c = 11.310 (5) Å	µ = 0.08 mm−1
α = 73.25 (4)°	T = 291 K
β = 72.25 (3)°	Prism, colourless
γ = 66.05 (3)°	0.40 × 0.35 × 0.30 mm
V = 724.3 (5) Å3

Enraf–Nonius TurboCAD-4 diffractometer	1689 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.015
graphite	θmax = 25.0°, θmin = 1.9°
non–profiled ω/2τ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −9→10
Tmin = 0.965, Tmax = 0.979	l = −12→13
2735 measured reflections	3 standard reflections every 166 min
2548 independent reflections	intensity decay: 1%

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1543P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2548 reflections	Δρmax = 0.12 e Å−3
164 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.064 (6)

Experimental. Number of psi-scan sets used was 5. 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	1.0848 (3)	−0.3377 (3)	0.8308 (3)	0.0843 (7)
H1	1.1732	−0.4115	0.8727	0.101*
C2	1.1205 (3)	−0.2955 (3)	0.7023 (3)	0.0828 (7)
H2	1.2336	−0.3389	0.6568	0.099*
C3	0.9887 (3)	−0.1880 (3)	0.6390 (2)	0.0663 (6)
H3	1.0133	−0.1619	0.5511	0.08*
C4	0.8198 (2)	−0.1190 (2)	0.70634 (18)	0.0499 (5)
C5	0.7874 (3)	−0.1610 (3)	0.83672 (19)	0.0572 (5)
H5	0.6759	−0.1144	0.8835	0.069*
C6	0.9192 (3)	−0.2718 (3)	0.8982 (2)	0.0715 (6)
H6	0.8953	−0.3017	0.986	0.086*
C7	0.6830 (3)	−0.0021 (3)	0.63224 (18)	0.0535 (5)
O1	0.7093 (2)	−0.0062 (2)	0.52144 (14)	0.0808 (5)
C8	0.5114 (2)	0.1223 (2)	0.69448 (18)	0.0521 (5)
C9	0.4249 (3)	0.2636 (3)	0.5920 (2)	0.0755 (7)
H9B	0.5024	0.3236	0.5419	0.113*
H9C	0.3191	0.3425	0.6314	0.113*
H9A	0.3993	0.2127	0.5387	0.113*
C10	0.3865 (3)	0.0253 (3)	0.7712 (2)	0.0707 (6)
H10A	0.3667	−0.0282	0.7166	0.106*
H10B	0.2779	0.1043	0.8075	0.106*
H10C	0.4368	−0.0608	0.8375	0.106*
C11	0.5454 (2)	0.2112 (2)	0.77688 (18)	0.0505 (5)
O2	0.4621 (2)	0.2339 (2)	0.88045 (14)	0.0736 (5)
O3	0.67818 (16)	0.26535 (16)	0.71377 (11)	0.0533 (4)
C12	0.7438 (3)	0.3557 (3)	0.7690 (2)	0.0616 (6)
C13	0.8897 (3)	0.3905 (4)	0.6630 (3)	0.0942 (9)
H13A	0.845	0.4548	0.5885	0.141*
H13B	0.9783	0.2838	0.6455	0.141*
H13C	0.9384	0.4551	0.6876	0.141*
C14	0.6027 (4)	0.5217 (3)	0.7977 (3)	0.1024 (10)
H14A	0.5558	0.5852	0.724	0.154*
H14B	0.6503	0.588	0.8214	0.154*
H14C	0.512	0.4977	0.8659	0.154*
C15	0.8130 (4)	0.2379 (4)	0.8824 (3)	0.1046 (10)
H15A	0.8952	0.1314	0.8593	0.157*
H15B	0.7186	0.2168	0.9482	0.157*
H15C	0.8692	0.2902	0.9121	0.157*

	U11	U22	U33	U12	U13	U23
C1	0.0638 (15)	0.0716 (16)	0.103 (2)	−0.0149 (12)	−0.0227 (14)	−0.0031 (14)
C2	0.0506 (13)	0.0702 (15)	0.104 (2)	−0.0101 (12)	0.0024 (13)	−0.0182 (14)
C3	0.0647 (14)	0.0601 (13)	0.0670 (13)	−0.0244 (12)	0.0047 (11)	−0.0175 (11)
C4	0.0526 (11)	0.0448 (10)	0.0568 (11)	−0.0232 (9)	−0.0039 (9)	−0.0154 (9)
C5	0.0517 (11)	0.0579 (12)	0.0588 (12)	−0.0185 (10)	−0.0068 (10)	−0.0128 (10)
C6	0.0676 (15)	0.0702 (14)	0.0704 (14)	−0.0210 (12)	−0.0186 (12)	−0.0048 (12)
C7	0.0608 (12)	0.0618 (12)	0.0526 (11)	−0.0349 (10)	−0.0080 (9)	−0.0165 (9)
O1	0.0838 (11)	0.1121 (13)	0.0602 (10)	−0.0381 (10)	−0.0145 (8)	−0.0314 (9)
C8	0.0507 (11)	0.0547 (11)	0.0587 (11)	−0.0244 (9)	−0.0149 (9)	−0.0099 (9)
C9	0.0812 (16)	0.0708 (15)	0.0853 (16)	−0.0268 (12)	−0.0395 (13)	−0.0069 (12)
C10	0.0558 (12)	0.0752 (15)	0.0921 (16)	−0.0357 (11)	−0.0118 (11)	−0.0172 (12)
C11	0.0473 (11)	0.0503 (11)	0.0544 (11)	−0.0187 (9)	−0.0091 (9)	−0.0101 (9)
O2	0.0743 (10)	0.0925 (11)	0.0624 (9)	−0.0433 (9)	0.0091 (8)	−0.0310 (8)
O3	0.0550 (8)	0.0628 (8)	0.0547 (8)	−0.0329 (7)	−0.0061 (6)	−0.0173 (6)
C12	0.0660 (13)	0.0680 (13)	0.0706 (14)	−0.0348 (11)	−0.0167 (11)	−0.0229 (11)
C13	0.0884 (18)	0.121 (2)	0.106 (2)	−0.0729 (18)	−0.0038 (15)	−0.0332 (17)
C14	0.097 (2)	0.0794 (18)	0.154 (3)	−0.0341 (16)	−0.0215 (19)	−0.0580 (18)
C15	0.119 (2)	0.130 (2)	0.100 (2)	−0.064 (2)	−0.0581 (19)	−0.0060 (18)

C1—C2	1.360 (3)	C9—H9A	0.96
C1—C6	1.368 (3)	C10—H10A	0.96
C1—H1	0.93	C10—H10B	0.96
C2—C3	1.387 (3)	C10—H10C	0.96
C2—H2	0.93	C11—O2	1.197 (2)
C3—C4	1.391 (3)	C11—O3	1.336 (2)
C3—H3	0.93	O3—C12	1.479 (2)
C4—C5	1.381 (3)	C12—C15	1.504 (3)
C4—C7	1.505 (3)	C12—C14	1.507 (3)
C5—C6	1.382 (3)	C12—C13	1.514 (3)
C5—H5	0.93	C13—H13A	0.96
C6—H6	0.93	C13—H13B	0.96
C7—O1	1.212 (2)	C13—H13C	0.96
C7—C8	1.535 (3)	C14—H14A	0.96
C8—C11	1.522 (3)	C14—H14B	0.96
C8—C10	1.540 (3)	C14—H14C	0.96
C8—C9	1.540 (3)	C15—H15A	0.96
C9—H9B	0.96	C15—H15B	0.96
C9—H9C	0.96	C15—H15C	0.96
C2—C1—C6	120.1 (2)	C8—C10—H10B	109.5
C2—C1—H1	119.9	H10A—C10—H10B	109.5
C6—C1—H1	119.9	C8—C10—H10C	109.5
C1—C2—C3	120.2 (2)	H10A—C10—H10C	109.5
C1—C2—H2	119.9	H10B—C10—H10C	109.5
C3—C2—H2	119.9	O2—C11—O3	125.43 (18)
C2—C3—C4	120.3 (2)	O2—C11—C8	125.07 (17)
C2—C3—H3	119.8	O3—C11—C8	109.46 (16)
C4—C3—H3	119.8	C11—O3—C12	122.50 (15)
C5—C4—C3	118.4 (2)	O3—C12—C15	109.11 (18)
C5—C4—C7	123.82 (18)	O3—C12—C14	109.65 (17)
C3—C4—C7	117.79 (18)	C15—C12—C14	113.7 (2)
C4—C5—C6	120.6 (2)	O3—C12—C13	102.51 (16)
C4—C5—H5	119.7	C15—C12—C13	110.8 (2)
C6—C5—H5	119.7	C14—C12—C13	110.4 (2)
C1—C6—C5	120.3 (2)	C12—C13—H13A	109.5
C1—C6—H6	119.8	C12—C13—H13B	109.5
C5—C6—H6	119.8	H13A—C13—H13B	109.5
O1—C7—C4	119.24 (19)	C12—C13—H13C	109.5
O1—C7—C8	119.62 (19)	H13A—C13—H13C	109.5
C4—C7—C8	121.14 (16)	H13B—C13—H13C	109.5
C11—C8—C7	110.39 (15)	C12—C14—H14A	109.5
C11—C8—C10	111.49 (17)	C12—C14—H14B	109.5
C7—C8—C10	109.80 (16)	H14A—C14—H14B	109.5
C11—C8—C9	106.87 (16)	C12—C14—H14C	109.5
C7—C8—C9	109.79 (17)	H14A—C14—H14C	109.5
C10—C8—C9	108.42 (17)	H14B—C14—H14C	109.5
C8—C9—H9B	109.5	C12—C15—H15A	109.5
C8—C9—H9C	109.5	C12—C15—H15B	109.5
H9B—C9—H9C	109.5	H15A—C15—H15B	109.5
C8—C9—H9A	109.5	C12—C15—H15C	109.5
H9B—C9—H9A	109.5	H15A—C15—H15C	109.5
H9C—C9—H9A	109.5	H15B—C15—H15C	109.5
C8—C10—H10A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.66	3.317 (3)	128
C9—H9A···O1ii	0.96	2.65	3.557 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.66	3.317 (3)	128
C9—H9A⋯O1ii	0.96	2.65	3.557 (3)	158

Symmetry codes: (i) ; (ii) .