Acet-oxy-γ-valerolactone.

Levulinyl cellulose esters have been produced as an effective renewable binder for architectural coatings. The title compound, C7H10O4 (systematic name: 2-methyl-5-oxo-tetra-hydro-furan-2-yl acetate), assigned as the esterifying species, was isolated and crystallized to confirm the structure. In the crystal, the mol-ecules pack in layers parallel to (102) utilizing weak C-H⋯O inter-actions.

Related literature

For related structures, see: Cai et al. (2004 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). For background information, see: Bredt (1886 ▶); Rasmussen & Brattain (1949 ▶); Suami & Day (1959 ▶); Glenny et al. (2012 ▶). For a previous description of the title compound but without supporting crystal structure data, see: Bell & Covington (1975 ▶).

Experimental

Crystal data

C7H10O4

M = 158.15

Monoclinic,

a = 5.86715 (15) Å

b = 12.7280 (3) Å

c = 10.2756 (3) Å

β = 106.020 (3)°

V = 737.55 (3) Å3

Z = 4

Cu Kα radiation

μ = 1.00 mm−1

T = 120 K

0.19 × 0.12 × 0.07 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.812, T max = 1.000

4959 measured reflections

1469 independent reflections

1350 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.03

1469 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: ORTEP in WinGX (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL2012 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013561/cv5410sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013561/cv5410Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013561/cv5410Isup3.cml

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

C7H10O4	F(000) = 336
Mr = 158.15	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 5.86715 (15) Å	Cell parameters from 3083 reflections
b = 12.7280 (3) Å	θ = 5.7–73.5°
c = 10.2756 (3) Å	µ = 1.00 mm−1
β = 106.020 (3)°	T = 120 K
V = 737.55 (3) Å3	Block, colourless
Z = 4	0.19 × 0.12 × 0.07 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	1469 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1350 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 5.3250 pixels mm-1	θmax = 73.8°, θmin = 5.7°
ω scans	h = −7→7
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013)	k = −13→15
Tmin = 0.812, Tmax = 1.000	l = −12→12
4959 measured reflections

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) = 0.084	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.1941P] where P = (Fo2 + 2Fc2)/3
1469 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2013); numerical absorption correction based on gaussian integration over a multifaceted crystal model

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.

	x	y	z	Uiso*/Ueq
O1	0.25087 (13)	0.23353 (6)	0.37683 (8)	0.01787 (19)
O2	0.01399 (17)	0.10362 (7)	0.27499 (9)	0.0268 (2)
O3	0.32805 (14)	0.40425 (6)	0.32322 (8)	0.0179 (2)
O4	0.04509 (15)	0.35237 (6)	0.13677 (8)	0.0226 (2)
C1	0.4004 (2)	0.36108 (9)	0.55163 (11)	0.0217 (3)
H1A	0.3518	0.3185	0.6188	0.033*
H1B	0.3959	0.4356	0.5747	0.033*
H1C	0.5620	0.3418	0.5514	0.033*
C2	0.23376 (19)	0.34162 (8)	0.41354 (11)	0.0166 (2)
C3	−0.0297 (2)	0.36272 (9)	0.40270 (11)	0.0187 (2)
H3A	−0.0526	0.3758	0.4932	0.022*
H3B	−0.0882	0.4243	0.3442	0.022*
C4	−0.1589 (2)	0.26306 (9)	0.34032 (12)	0.0206 (2)
H4A	−0.2462	0.2319	0.4007	0.025*
H4B	−0.2728	0.2785	0.2516	0.025*
C5	0.0322 (2)	0.18993 (9)	0.32378 (11)	0.0187 (2)
C6	0.2205 (2)	0.40306 (8)	0.18841 (11)	0.0185 (2)
C7	0.3555 (2)	0.46800 (9)	0.11343 (12)	0.0236 (3)
H7A	0.4708	0.4236	0.0862	0.035*
H7B	0.4391	0.5245	0.1723	0.035*
H7C	0.2451	0.4984	0.0327	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0182 (4)	0.0148 (4)	0.0212 (4)	0.0003 (3)	0.0065 (3)	0.0008 (3)
O2	0.0346 (5)	0.0185 (4)	0.0294 (5)	−0.0052 (3)	0.0121 (4)	−0.0058 (3)
O3	0.0204 (4)	0.0174 (4)	0.0163 (4)	−0.0029 (3)	0.0059 (3)	0.0013 (3)
O4	0.0262 (4)	0.0233 (4)	0.0172 (4)	−0.0041 (3)	0.0043 (3)	−0.0009 (3)
C1	0.0218 (6)	0.0257 (6)	0.0163 (5)	−0.0040 (4)	0.0032 (4)	0.0019 (4)
C2	0.0191 (5)	0.0141 (5)	0.0173 (5)	−0.0015 (4)	0.0061 (4)	0.0007 (4)
C3	0.0189 (5)	0.0184 (5)	0.0197 (5)	0.0003 (4)	0.0069 (4)	−0.0021 (4)
C4	0.0182 (5)	0.0211 (5)	0.0223 (5)	−0.0024 (4)	0.0054 (4)	−0.0022 (4)
C5	0.0219 (5)	0.0185 (5)	0.0163 (5)	−0.0031 (4)	0.0065 (4)	0.0011 (4)
C6	0.0229 (6)	0.0160 (5)	0.0170 (5)	0.0022 (4)	0.0064 (4)	0.0004 (4)
C7	0.0293 (6)	0.0226 (6)	0.0207 (5)	−0.0026 (5)	0.0099 (5)	0.0023 (4)

O1—C5	1.3660 (14)	C3—C4	1.5253 (15)
O1—C2	1.4373 (13)	C3—H3A	0.9900
O2—C5	1.2000 (15)	C3—H3B	0.9900
O3—C6	1.3546 (14)	C4—C5	1.5025 (16)
O3—C2	1.4443 (13)	C4—H4A	0.9900
O4—C6	1.2063 (15)	C4—H4B	0.9900
C1—C2	1.5049 (15)	C6—C7	1.4972 (15)
C1—H1A	0.9800	C7—H7A	0.9800
C1—H1B	0.9800	C7—H7B	0.9800
C1—H1C	0.9800	C7—H7C	0.9800
C2—C3	1.5424 (15)
C5—O1—C2	111.57 (8)	H3A—C3—H3B	108.8
C6—O3—C2	119.86 (8)	C5—C4—C3	105.24 (9)
C2—C1—H1A	109.5	C5—C4—H4A	110.7
C2—C1—H1B	109.5	C3—C4—H4A	110.7
H1A—C1—H1B	109.5	C5—C4—H4B	110.7
C2—C1—H1C	109.5	C3—C4—H4B	110.7
H1A—C1—H1C	109.5	H4A—C4—H4B	108.8
H1B—C1—H1C	109.5	O2—C5—O1	120.27 (11)
O1—C2—O3	107.02 (8)	O2—C5—C4	129.16 (11)
O1—C2—C1	109.32 (9)	O1—C5—C4	110.56 (9)
O3—C2—C1	104.52 (9)	O4—C6—O3	123.78 (10)
O1—C2—C3	106.79 (8)	O4—C6—C7	125.25 (10)
O3—C2—C3	114.29 (9)	O3—C6—C7	110.90 (10)
C1—C2—C3	114.62 (9)	C6—C7—H7A	109.5
C4—C3—C2	104.93 (9)	C6—C7—H7B	109.5
C4—C3—H3A	110.8	H7A—C7—H7B	109.5
C2—C3—H3A	110.8	C6—C7—H7C	109.5
C4—C3—H3B	110.8	H7A—C7—H7C	109.5
C2—C3—H3B	110.8	H7B—C7—H7C	109.5
C5—O1—C2—O3	−112.79 (9)	C1—C2—C3—C4	−128.27 (10)
C5—O1—C2—C1	134.56 (9)	C2—C3—C4—C5	2.08 (11)
C5—O1—C2—C3	10.02 (11)	C2—O1—C5—O2	172.31 (10)
C6—O3—C2—O1	62.87 (11)	C2—O1—C5—C4	−8.92 (12)
C6—O3—C2—C1	178.76 (9)	C3—C4—C5—O2	−177.45 (11)
C6—O3—C2—C3	−55.15 (12)	C3—C4—C5—O1	3.91 (12)
O1—C2—C3—C4	−7.04 (11)	C2—O3—C6—O4	0.50 (16)
O3—C2—C3—C4	111.11 (10)	C2—O3—C6—C7	−176.52 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O2i	0.99	2.68	3.5827 (13)	152
C1—H1B···O3ii	0.98	2.63	3.4617 (14)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O2i	0.99	2.68	3.5827 (13)	152
C1—H1B⋯O3ii	0.98	2.63	3.4617 (14)	142

Symmetry codes: (i) ; (ii) .