Dimethyl 4,4-diacetyl-hepta-nedioate.

The mol-ecule of the title dicarbonyl compound, C(13)H(20)O(6), possesses approximate local twofold symmetry. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules, generating a chain structure.

Related literature

For general background, see: Kim et al. (2001 ▶); Chetia et al. (2004 ▶); Ranu & Banerjee (2005 ▶); Wang et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H20O6

M = 272.29

Monoclinic,

a = 11.402 (2) Å

b = 8.6910 (17) Å

c = 14.845 (3) Å

β = 107.35 (3)°

V = 1404.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.970, T max = 0.990

2531 measured reflections

2531 independent reflections

1783 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: 9%

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.202

S = 1.01

2531 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043705/sj2570sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043705/sj2570Isup2.hkl

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

C13H20O6	F(000) = 584
Mr = 272.29	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 27 reflections
a = 11.402 (2) Å	θ = 8–15°
b = 8.6910 (17) Å	µ = 0.10 mm−1
c = 14.845 (3) Å	T = 293 K
β = 107.35 (3)°	Block, colourless
V = 1404.1 (5) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 25.3°, θmin = 1.9°
ω/2θ scans	h = −13→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.970, Tmax = 0.990	l = 0→17
2531 measured reflections	3 standard reflections every 200 reflections
2531 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3
2531 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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 > σ(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	1.1970 (2)	−0.2798 (3)	0.80271 (19)	0.0587 (7)
O2	1.1274 (2)	−0.0419 (2)	0.80976 (18)	0.0552 (7)
O3	0.5191 (2)	−0.3553 (3)	0.66776 (18)	0.0646 (7)
O4	0.5065 (2)	−0.1212 (3)	0.60519 (17)	0.0585 (7)
O5	0.7976 (2)	0.0496 (2)	0.94983 (17)	0.0506 (6)
O6	0.8453 (2)	−0.4676 (2)	0.96422 (18)	0.0567 (7)
C1	1.2919 (4)	−0.2184 (5)	0.7683 (3)	0.0710 (12)
H1A	1.3430	−0.3006	0.7586	0.106*
H1B	1.3407	−0.1472	0.8136	0.106*
H1C	1.2556	−0.1660	0.7097	0.106*
C2	1.1177 (3)	−0.1782 (3)	0.8194 (2)	0.0401 (7)
C3	1.0191 (3)	−0.2557 (3)	0.8502 (2)	0.0408 (7)
H3A	1.0564	−0.3225	0.9033	0.049*
H3B	0.9697	−0.3190	0.7991	0.049*
C4	0.9365 (2)	−0.1393 (3)	0.8785 (2)	0.0360 (7)
H4A	0.9057	−0.0673	0.8269	0.043*
H4B	0.9858	−0.0814	0.9324	0.043*
C5	0.4002 (3)	−0.1660 (5)	0.5299 (3)	0.0597 (10)
H5A	0.3724	−0.0805	0.4881	0.089*
H5B	0.3361	−0.1974	0.5557	0.089*
H5C	0.4211	−0.2501	0.4957	0.089*
C6	0.5572 (3)	−0.2265 (4)	0.6703 (2)	0.0430 (7)
C7	0.6632 (3)	−0.1613 (4)	0.7454 (2)	0.0513 (8)
H7A	0.6340	−0.0785	0.7769	0.062*
H7B	0.7214	−0.1179	0.7163	0.062*
C8	0.7290 (3)	−0.2793 (3)	0.8186 (2)	0.0413 (7)
H8A	0.7683	−0.3542	0.7887	0.050*
H8B	0.6686	−0.3333	0.8410	0.050*
C9	0.6618 (3)	−0.1291 (4)	0.9838 (3)	0.0582 (9)
H9A	0.6315	−0.0401	1.0081	0.087*
H9B	0.6907	−0.2033	1.0334	0.087*
H9C	0.5967	−0.1734	0.9338	0.087*
C10	0.7649 (3)	−0.0831 (4)	0.9467 (2)	0.0393 (7)
C11	0.9581 (3)	−0.2844 (4)	1.0738 (2)	0.0539 (9)
H11A	0.9808	−0.3720	1.1146	0.081*
H11B	0.9172	−0.2102	1.1018	0.081*
H11C	1.0305	−0.2389	1.0648	0.081*
C12	0.8733 (3)	−0.3344 (3)	0.9802 (2)	0.0394 (7)
C13	0.8265 (2)	−0.2094 (3)	0.9038 (2)	0.0341 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0587 (14)	0.0424 (13)	0.0902 (18)	0.0057 (11)	0.0453 (14)	0.0031 (12)
O2	0.0663 (15)	0.0377 (13)	0.0743 (16)	−0.0010 (11)	0.0403 (13)	0.0039 (11)
O3	0.0630 (16)	0.0488 (15)	0.0686 (16)	−0.0126 (12)	−0.0008 (13)	0.0054 (12)
O4	0.0587 (15)	0.0523 (14)	0.0544 (14)	−0.0080 (11)	0.0015 (11)	0.0059 (11)
O5	0.0508 (13)	0.0329 (12)	0.0712 (16)	0.0012 (10)	0.0228 (11)	−0.0047 (10)
O6	0.0595 (15)	0.0344 (13)	0.0714 (16)	−0.0049 (10)	0.0123 (12)	0.0102 (11)
C1	0.065 (2)	0.063 (2)	0.105 (3)	−0.0007 (19)	0.055 (2)	−0.006 (2)
C2	0.0444 (17)	0.0383 (17)	0.0393 (16)	−0.0001 (13)	0.0149 (13)	−0.0041 (12)
C3	0.0439 (16)	0.0348 (15)	0.0472 (17)	0.0000 (13)	0.0188 (13)	0.0000 (12)
C4	0.0335 (15)	0.0300 (14)	0.0444 (16)	−0.0032 (12)	0.0114 (12)	−0.0044 (12)
C5	0.0441 (19)	0.075 (3)	0.053 (2)	0.0015 (18)	0.0036 (16)	0.0057 (18)
C6	0.0394 (16)	0.0485 (19)	0.0436 (17)	−0.0009 (14)	0.0163 (14)	−0.0008 (14)
C7	0.0530 (19)	0.0474 (19)	0.0449 (17)	−0.0104 (15)	0.0013 (15)	0.0036 (15)
C8	0.0409 (16)	0.0355 (16)	0.0468 (17)	−0.0046 (13)	0.0122 (14)	−0.0004 (13)
C9	0.050 (2)	0.060 (2)	0.075 (2)	0.0021 (17)	0.0360 (18)	0.0016 (18)
C10	0.0316 (15)	0.0415 (17)	0.0423 (16)	0.0022 (13)	0.0072 (12)	−0.0005 (13)
C11	0.065 (2)	0.0460 (19)	0.0474 (19)	0.0052 (16)	0.0111 (16)	0.0047 (15)
C12	0.0385 (15)	0.0337 (16)	0.0499 (17)	0.0005 (12)	0.0191 (13)	0.0033 (13)
C13	0.0322 (14)	0.0293 (14)	0.0408 (15)	−0.0007 (11)	0.0108 (12)	−0.0010 (11)

O1—C2	1.339 (4)	C5—H5B	0.9600
O1—C1	1.430 (4)	C5—H5C	0.9600
O2—C2	1.202 (4)	C6—C7	1.491 (4)
O3—C6	1.197 (4)	C7—C8	1.519 (4)
O4—C6	1.331 (4)	C7—H7A	0.9700
O4—C5	1.436 (4)	C7—H7B	0.9700
O5—C10	1.209 (4)	C8—C13	1.538 (4)
O6—C12	1.206 (4)	C8—H8A	0.9700
C1—H1A	0.9600	C8—H8B	0.9700
C1—H1B	0.9600	C9—C10	1.494 (4)
C1—H1C	0.9600	C9—H9A	0.9600
C2—C3	1.495 (4)	C9—H9B	0.9600
C3—C4	1.524 (4)	C9—H9C	0.9600
C3—H3A	0.9700	C10—C13	1.540 (4)
C3—H3B	0.9700	C11—C12	1.501 (5)
C4—C13	1.539 (4)	C11—H11A	0.9600
C4—H4A	0.9700	C11—H11B	0.9600
C4—H4B	0.9700	C11—H11C	0.9600
C5—H5A	0.9600	C12—C13	1.546 (4)
C2—O1—C1	116.4 (3)	C8—C7—H7A	108.9
C6—O4—C5	117.5 (3)	C6—C7—H7B	108.9
O1—C1—H1A	109.5	C8—C7—H7B	108.9
O1—C1—H1B	109.5	H7A—C7—H7B	107.7
H1A—C1—H1B	109.5	C7—C8—C13	113.8 (2)
O1—C1—H1C	109.5	C7—C8—H8A	108.8
H1A—C1—H1C	109.5	C13—C8—H8A	108.8
H1B—C1—H1C	109.5	C7—C8—H8B	108.8
O2—C2—O1	122.5 (3)	C13—C8—H8B	108.8
O2—C2—C3	125.8 (3)	H8A—C8—H8B	107.7
O1—C2—C3	111.8 (3)	C10—C9—H9A	109.5
C2—C3—C4	111.6 (2)	C10—C9—H9B	109.5
C2—C3—H3A	109.3	H9A—C9—H9B	109.5
C4—C3—H3A	109.3	C10—C9—H9C	109.5
C2—C3—H3B	109.3	H9A—C9—H9C	109.5
C4—C3—H3B	109.3	H9B—C9—H9C	109.5
H3A—C3—H3B	108.0	O5—C10—C9	120.6 (3)
C3—C4—C13	114.8 (2)	O5—C10—C13	121.5 (3)
C3—C4—H4A	108.6	C9—C10—C13	117.9 (3)
C13—C4—H4A	108.6	C12—C11—H11A	109.5
C3—C4—H4B	108.6	C12—C11—H11B	109.5
C13—C4—H4B	108.6	H11A—C11—H11B	109.5
H4A—C4—H4B	107.5	C12—C11—H11C	109.5
O4—C5—H5A	109.5	H11A—C11—H11C	109.5
O4—C5—H5B	109.5	H11B—C11—H11C	109.5
H5A—C5—H5B	109.5	O6—C12—C11	121.3 (3)
O4—C5—H5C	109.5	O6—C12—C13	121.1 (3)
H5A—C5—H5C	109.5	C11—C12—C13	117.5 (3)
H5B—C5—H5C	109.5	C8—C13—C4	113.4 (2)
O3—C6—O4	123.0 (3)	C8—C13—C10	108.4 (2)
O3—C6—C7	125.7 (3)	C4—C13—C10	108.9 (2)
O4—C6—C7	111.2 (3)	C8—C13—C12	109.4 (2)
C6—C7—C8	113.3 (3)	C4—C13—C12	109.2 (2)
C6—C7—H7A	108.9	C10—C13—C12	107.3 (2)
C1—O1—C2—O2	−2.7 (5)	C3—C4—C13—C10	170.5 (2)
C1—O1—C2—C3	177.0 (3)	C3—C4—C13—C12	53.6 (3)
O2—C2—C3—C4	−5.9 (4)	O5—C10—C13—C8	−118.2 (3)
O1—C2—C3—C4	174.3 (3)	C9—C10—C13—C8	61.1 (3)
C2—C3—C4—C13	175.5 (2)	O5—C10—C13—C4	5.6 (4)
C5—O4—C6—O3	0.9 (5)	C9—C10—C13—C4	−175.1 (3)
C5—O4—C6—C7	−177.8 (3)	O5—C10—C13—C12	123.7 (3)
O3—C6—C7—C8	4.6 (5)	C9—C10—C13—C12	−57.0 (3)
O4—C6—C7—C8	−176.7 (3)	O6—C12—C13—C8	9.0 (4)
C6—C7—C8—C13	−171.8 (3)	C11—C12—C13—C8	−172.9 (3)
C7—C8—C13—C4	−66.3 (3)	O6—C12—C13—C4	−115.7 (3)
C7—C8—C13—C10	54.8 (3)	C11—C12—C13—C4	62.4 (3)
C7—C8—C13—C12	171.5 (3)	O6—C12—C13—C10	126.4 (3)
C3—C4—C13—C8	−68.8 (3)	C11—C12—C13—C10	−55.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O5i	0.97	2.58	3.418 (4)	145
C3—H3B···O2ii	0.97	2.55	3.500 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O5i	0.97	2.58	3.418 (4)	145
C3—H3B⋯O2ii	0.97	2.55	3.500 (4)	165

Symmetry codes: (i) ; (ii) .