(S)-6-Methyl-∊-caprolactone.

The chiral title compound, C(7)H(12)O(2), a lactone derivative, features a seven-membered ring that adopts a chair conformation. The crystal structure is stabilized by weak C-H⋯O inter-actions occurring in the (100) plane. The absolute configuration was assigned on the basis of the enantioselective synthesis.

Related literature

For related literature, see: van As et al. (2005 ▶); van Buijtenen et al. (2006 ▶). For details of the synthesis, see: van As et al. (2007 ▶). For geometry, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C7H12O2

M = 128.17

Monoclinic,

a = 6.757 (2) Å

b = 7.577 (2) Å

c = 7.586 (2) Å

β = 110.949 (13)°

V = 362.71 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 150 (2) K

0.35 × 0.15 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

10010 measured reflections

889 independent reflections

862 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.072

S = 1.10

889 reflections

83 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004583/tk2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004583/tk2248Isup2.hkl

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

C7H12O2	F000 = 140
Mr = 128.17	Dx = 1.174 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7835 reflections
a = 6.757 (2) Å	θ = 1.0–27.5º
b = 7.577 (2) Å	µ = 0.08 mm−1
c = 7.586 (2) Å	T = 150 (2) K
β = 110.949 (13)º	Prism, colourless
V = 362.71 (17) Å3	0.35 × 0.15 × 0.10 mm
Z = 2

Nonius KappaCCD diffractometer	862 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.041
Monochromator: graphite	θmax = 27.5º
T = 150(2) K	θmin = 3.5º
φ and ω scans	h = −8→8
Absorption correction: none	k = −9→9
10010 measured reflections	l = −9→9
889 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.0282P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
889 reflections	Δρmax = 0.12 e Å−3
83 parameters	Δρmin = −0.16 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: known chirality of atom C6(S)

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 > 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
O1	1.03545 (16)	0.06828 (15)	−0.16671 (13)	0.0355 (3)
O2	1.11573 (13)	0.04935 (14)	0.13758 (12)	0.0288 (2)
C1	0.9754 (2)	0.03155 (18)	−0.03896 (16)	0.0258 (3)
C2	0.7534 (2)	−0.0285 (2)	−0.07029 (18)	0.0301 (3)
H2A	0.7594	−0.1422	−0.0042	0.036*
H2B	0.6778	−0.0491	−0.2069	0.036*
C3	0.6274 (2)	0.1054 (2)	0.0003 (2)	0.0356 (3)
H3A	0.6603	0.2261	−0.0311	0.043*
H3B	0.4740	0.0849	−0.0669	0.043*
C4	0.6759 (2)	0.0938 (2)	0.2120 (2)	0.0365 (3)
H4A	0.6389	−0.0260	0.2421	0.044*
H4B	0.5841	0.1787	0.2461	0.044*
C5	0.9066 (2)	0.1315 (2)	0.33415 (18)	0.0303 (3)
H5A	0.9423	0.2528	0.3071	0.036*
H5B	0.9205	0.1274	0.4685	0.036*
C6	1.06592 (19)	0.00512 (19)	0.30521 (16)	0.0267 (3)
H6	1.0098	−0.1181	0.2938	0.032*
C7	1.2785 (2)	0.0148 (3)	0.46522 (19)	0.0403 (4)
H7A	1.3333	0.1356	0.4759	0.060*
H7B	1.3783	−0.0660	0.4396	0.060*
H7C	1.2615	−0.0190	0.5837	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0442 (5)	0.0406 (6)	0.0260 (5)	0.0001 (5)	0.0177 (4)	0.0018 (4)
O2	0.0248 (4)	0.0400 (6)	0.0219 (4)	−0.0028 (4)	0.0087 (3)	0.0022 (4)
C1	0.0305 (6)	0.0245 (6)	0.0221 (6)	0.0029 (5)	0.0093 (5)	−0.0007 (5)
C2	0.0272 (6)	0.0341 (7)	0.0255 (6)	−0.0021 (5)	0.0050 (5)	−0.0041 (6)
C3	0.0242 (6)	0.0431 (9)	0.0365 (7)	0.0058 (6)	0.0074 (5)	0.0002 (7)
C4	0.0298 (6)	0.0451 (9)	0.0382 (7)	0.0031 (6)	0.0166 (5)	−0.0030 (7)
C5	0.0360 (7)	0.0322 (7)	0.0254 (6)	−0.0015 (6)	0.0143 (5)	−0.0026 (5)
C6	0.0265 (6)	0.0330 (7)	0.0202 (6)	−0.0027 (5)	0.0079 (5)	0.0028 (5)
C7	0.0311 (6)	0.0598 (11)	0.0252 (6)	−0.0040 (7)	0.0043 (5)	0.0070 (7)

O1—C1	1.2095 (16)	C4—H4A	0.9900
O2—C1	1.3428 (15)	C4—H4B	0.9900
O2—C6	1.4659 (14)	C5—C6	1.5140 (19)
C1—C2	1.5028 (18)	C5—H5A	0.9900
C2—C3	1.539 (2)	C5—H5B	0.9900
C2—H2A	0.9900	C6—C7	1.5152 (18)
C2—H2B	0.9900	C6—H6	1.0000
C3—C4	1.523 (2)	C7—H7A	0.9800
C3—H3A	0.9900	C7—H7B	0.9800
C3—H3B	0.9900	C7—H7C	0.9800
C4—C5	1.5288 (19)
C1—O2—C6	122.88 (10)	C5—C4—H4B	108.6
O1—C1—O2	117.15 (12)	H4A—C4—H4B	107.6
O1—C1—C2	123.02 (11)	C6—C5—C4	114.69 (12)
O2—C1—C2	119.82 (11)	C6—C5—H5A	108.6
C1—C2—C3	112.99 (12)	C4—C5—H5A	108.6
C1—C2—H2A	109.0	C6—C5—H5B	108.6
C3—C2—H2A	109.0	C4—C5—H5B	108.6
C1—C2—H2B	109.0	H5A—C5—H5B	107.6
C3—C2—H2B	109.0	O2—C6—C5	112.13 (11)
H2A—C2—H2B	107.8	O2—C6—C7	103.76 (10)
C4—C3—C2	113.05 (12)	C5—C6—C7	111.89 (12)
C4—C3—H3A	109.0	O2—C6—H6	109.6
C2—C3—H3A	109.0	C5—C6—H6	109.6
C4—C3—H3B	109.0	C7—C6—H6	109.6
C2—C3—H3B	109.0	C6—C7—H7A	109.5
H3A—C3—H3B	107.8	C6—C7—H7B	109.5
C3—C4—C5	114.64 (11)	H7A—C7—H7B	109.5
C3—C4—H4A	108.6	C6—C7—H7C	109.5
C5—C4—H4A	108.6	H7A—C7—H7C	109.5
C3—C4—H4B	108.6	H7B—C7—H7C	109.5
C6—O2—C1—O1	−178.35 (12)	C3—C4—C5—C6	−61.49 (19)
C6—O2—C1—C2	2.78 (18)	C1—O2—C6—C5	−68.78 (16)
O1—C1—C2—C3	−112.90 (16)	C1—O2—C6—C7	170.29 (13)
O2—C1—C2—C3	65.90 (16)	C4—C5—C6—O2	80.45 (14)
C1—C2—C3—C4	−81.25 (16)	C4—C5—C6—C7	−163.43 (12)
C2—C3—C4—C5	61.39 (19)

C—H···O	C—H	H···O	C···O	C—H···A
C2—H2A···O1i	0.99	2.67	3.573 (2)	152
C5—H5A···O1ii	0.99	2.64	3.616 (2)	166
C5—H5B···O1ii	0.99	2.63	3.601 (2)	168
C6—H6···O1i	1.00	2.54	3.466 (2)	154

Table 1

Short-contact C—H⋯O interactions (Å, °) found in the (100) plane

C—H⋯O	C—H	H⋯O	C⋯O	C—H⋯A
C2—H2A⋯O1i	0.99	2.67	3.573 (2)	152
C5—H5A⋯O1ii	0.99	2.64	3.616 (2)	166
C5—H5B⋯O1ii	0.99	2.63	3.601 (2)	168
C6—H6⋯O1i	1.00	2.54	3.466 (2)	154

Symmetry codes: (i) ; (ii) .