2,2-Dimethyl-5-[(5-methyl-furan-2-yl)methyl-idene]-1,3-dioxane-4,6-dione.

The asymmetric unit of the title compound, C(12)H(12)O(5), contains two independent mol-ecules. In each, the 1,3-dioxane ring adopts an envelope conformation with the dimethyl-substituted C atom forming the flap. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Zeng (2010a ▶,b ▶).

Experimental

Crystal data

C12H12O5

M = 236.22

Triclinic,

a = 8.9590 (18) Å

b = 10.038 (2) Å

c = 13.616 (3) Å

α = 92.71 (3)°

β = 105.99 (3)°

γ = 91.67 (3)°

V = 1174.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.20 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

11592 measured reflections

5336 independent reflections

3333 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.156

S = 1.07

5336 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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/S1600536811002285/lh5196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002285/lh5196Isup2.hkl

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

C12H12O5	Z = 4
Mr = 236.22	F(000) = 496
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9590 (18) Å	Cell parameters from 3333 reflections
b = 10.038 (2) Å	θ = 3.1–27.5°
c = 13.616 (3) Å	µ = 0.11 mm−1
α = 92.71 (3)°	T = 293 K
β = 105.99 (3)°	Block, yellow
γ = 91.67 (3)°	0.20 × 0.16 × 0.12 mm
V = 1174.7 (4) Å3

Bruker SMART CCD area-detector diffractometer	3333 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.5°, θmin = 3.1°
φ and ω scans	h = −11→10
11592 measured reflections	k = −13→13
5336 independent reflections	l = −17→17

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0907P)2] where P = (Fo2 + 2Fc2)/3
5336 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.30 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
O2B	0.11969 (13)	0.55646 (11)	0.62210 (9)	0.0618 (3)
O5B	0.45369 (14)	1.05664 (10)	0.82774 (9)	0.0563 (3)
O1B	0.34137 (15)	0.48325 (11)	0.74003 (9)	0.0645 (3)
C5B	0.29935 (18)	0.71777 (15)	0.73236 (11)	0.0467 (4)
O3B	0.06239 (14)	0.76729 (12)	0.61279 (9)	0.0671 (3)
O4B	0.48827 (17)	0.61623 (12)	0.86197 (9)	0.0749 (4)
C6B	0.3859 (2)	0.60755 (16)	0.78319 (12)	0.0536 (4)
C7B	0.33715 (18)	0.84921 (15)	0.75839 (11)	0.0485 (4)
H7BA	0.2651	0.9054	0.7206	0.058*
C4B	0.15441 (19)	0.68642 (16)	0.65155 (12)	0.0522 (4)
C8B	0.46201 (19)	0.91860 (14)	0.83032 (11)	0.0481 (4)
C9B	0.5954 (2)	0.89135 (17)	0.90245 (12)	0.0564 (4)
H9BA	0.6302	0.8070	0.9202	0.068*
C3B	0.2442 (2)	0.46641 (16)	0.63735 (13)	0.0573 (4)
C11B	0.5813 (2)	1.11096 (17)	0.89765 (13)	0.0569 (4)
C10B	0.6699 (2)	1.01280 (18)	0.94451 (14)	0.0622 (4)
H10A	0.7635	1.0245	0.9955	0.075*
C1B	0.1707 (3)	0.32824 (18)	0.62731 (17)	0.0801 (6)
H1BA	0.1141	0.3201	0.6774	0.120*
H1BB	0.2501	0.2640	0.6381	0.120*
H1BC	0.1008	0.3123	0.5600	0.120*
C2B	0.3372 (3)	0.4908 (2)	0.56325 (16)	0.0780 (6)
H2BA	0.3813	0.5805	0.5749	0.117*
H2BB	0.2708	0.4787	0.4946	0.117*
H2BC	0.4191	0.4290	0.5728	0.117*
C12B	0.5961 (3)	1.25844 (18)	0.90908 (17)	0.0785 (6)
H12A	0.5088	1.2952	0.8619	0.118*
H12B	0.6903	1.2885	0.8950	0.118*
H12C	0.5986	1.2874	0.9778	0.118*
O5A	0.07339 (13)	0.59957 (9)	0.88357 (8)	0.0527 (3)
O2A	−0.36509 (13)	0.95250 (10)	0.63621 (9)	0.0573 (3)
O3A	−0.35857 (14)	0.73997 (11)	0.66614 (9)	0.0617 (3)
C5A	−0.14448 (18)	0.87879 (13)	0.76199 (11)	0.0447 (3)
O1A	−0.17387 (16)	1.11015 (10)	0.72684 (10)	0.0698 (4)
C8A	−0.05825 (18)	0.64850 (14)	0.81836 (11)	0.0447 (3)
C7A	−0.05103 (18)	0.78842 (14)	0.81679 (12)	0.0468 (4)
H7AA	0.0371	0.8277	0.8635	0.056*
C4A	−0.29180 (18)	0.84726 (14)	0.68578 (11)	0.0461 (4)
C6A	−0.0910 (2)	1.01900 (15)	0.78701 (14)	0.0596 (4)
O4A	0.01460 (18)	1.05984 (12)	0.85763 (12)	0.0924 (5)
C11A	0.0546 (2)	0.46486 (14)	0.87915 (13)	0.0529 (4)
C9A	−0.1573 (2)	0.54271 (14)	0.77519 (13)	0.0556 (4)
H9AA	−0.2548	0.5464	0.7287	0.067*
C3A	−0.2727 (2)	1.06729 (15)	0.62802 (13)	0.0592 (4)
C10A	−0.0843 (2)	0.42757 (15)	0.81423 (14)	0.0614 (5)
H10B	−0.1249	0.3404	0.7981	0.074*
C2A	−0.3843 (3)	1.17833 (18)	0.59790 (17)	0.0892 (7)
H2AA	−0.4385	1.1928	0.6490	0.134*
H2AB	−0.4578	1.1538	0.5332	0.134*
H2AC	−0.3273	1.2588	0.5924	0.134*
C12A	0.1835 (2)	0.39080 (17)	0.94262 (15)	0.0713 (5)
H12D	0.1569	0.2968	0.9333	0.107*
H12E	0.2009	0.4190	1.0134	0.107*
H12F	0.2763	0.4085	0.9223	0.107*
C1A	−0.1792 (3)	1.0368 (2)	0.55522 (18)	0.0901 (7)
H1AA	−0.1115	0.9659	0.5798	0.135*
H1AB	−0.1182	1.1149	0.5499	0.135*
H1AC	−0.2475	1.0099	0.4891	0.135*

	U11	U22	U33	U12	U13	U23
O2B	0.0499 (7)	0.0631 (7)	0.0632 (7)	−0.0012 (5)	0.0031 (6)	−0.0101 (6)
O5B	0.0605 (7)	0.0498 (6)	0.0555 (6)	0.0040 (5)	0.0110 (6)	0.0001 (5)
O1B	0.0751 (9)	0.0494 (6)	0.0566 (7)	0.0003 (5)	−0.0020 (6)	0.0017 (5)
C5B	0.0457 (9)	0.0530 (8)	0.0388 (8)	0.0032 (6)	0.0071 (7)	0.0021 (6)
O3B	0.0566 (8)	0.0765 (8)	0.0591 (7)	0.0159 (6)	0.0000 (6)	0.0020 (6)
O4B	0.0855 (10)	0.0592 (7)	0.0587 (8)	0.0038 (6)	−0.0165 (7)	0.0077 (6)
C6B	0.0573 (10)	0.0513 (9)	0.0462 (9)	0.0001 (7)	0.0048 (8)	0.0017 (7)
C7B	0.0483 (9)	0.0521 (8)	0.0441 (8)	0.0068 (7)	0.0102 (7)	0.0045 (7)
C4B	0.0492 (9)	0.0614 (9)	0.0452 (8)	0.0050 (7)	0.0119 (7)	0.0006 (7)
C8B	0.0540 (9)	0.0444 (8)	0.0448 (8)	0.0049 (6)	0.0119 (7)	0.0017 (6)
C9B	0.0564 (10)	0.0574 (9)	0.0510 (9)	0.0078 (7)	0.0073 (8)	0.0010 (8)
C3B	0.0585 (11)	0.0549 (9)	0.0519 (9)	0.0040 (7)	0.0055 (8)	−0.0035 (7)
C11B	0.0587 (11)	0.0580 (10)	0.0537 (9)	−0.0044 (8)	0.0174 (8)	−0.0079 (8)
C10B	0.0556 (11)	0.0672 (11)	0.0557 (10)	−0.0018 (8)	0.0041 (8)	−0.0068 (8)
C1B	0.0866 (15)	0.0621 (11)	0.0799 (13)	−0.0109 (10)	0.0070 (12)	−0.0092 (10)
C2B	0.0880 (15)	0.0808 (13)	0.0711 (12)	0.0114 (11)	0.0326 (12)	−0.0039 (10)
C12B	0.0895 (16)	0.0570 (11)	0.0872 (14)	−0.0067 (10)	0.0246 (12)	−0.0075 (10)
O5A	0.0561 (7)	0.0374 (5)	0.0592 (7)	0.0039 (4)	0.0061 (5)	0.0076 (5)
O2A	0.0550 (7)	0.0492 (6)	0.0600 (7)	0.0048 (5)	0.0018 (5)	0.0103 (5)
O3A	0.0549 (7)	0.0477 (6)	0.0712 (8)	−0.0089 (5)	0.0001 (6)	0.0026 (5)
C5A	0.0480 (9)	0.0354 (7)	0.0479 (8)	0.0017 (6)	0.0090 (7)	0.0018 (6)
O1A	0.0849 (9)	0.0341 (5)	0.0708 (8)	0.0066 (5)	−0.0116 (7)	0.0015 (5)
C8A	0.0480 (9)	0.0367 (7)	0.0473 (8)	0.0040 (6)	0.0092 (7)	0.0059 (6)
C7A	0.0463 (9)	0.0392 (7)	0.0506 (8)	−0.0023 (6)	0.0073 (7)	−0.0013 (6)
C4A	0.0493 (9)	0.0410 (8)	0.0469 (8)	0.0027 (6)	0.0113 (7)	0.0024 (6)
C6A	0.0624 (11)	0.0376 (8)	0.0660 (11)	0.0023 (7)	−0.0038 (9)	0.0035 (7)
O4A	0.0940 (11)	0.0423 (6)	0.1015 (11)	−0.0076 (6)	−0.0370 (9)	0.0016 (7)
C11A	0.0673 (11)	0.0376 (7)	0.0568 (9)	0.0069 (7)	0.0209 (9)	0.0080 (7)
C9A	0.0588 (10)	0.0407 (8)	0.0623 (10)	−0.0016 (7)	0.0094 (8)	0.0012 (7)
C3A	0.0724 (12)	0.0395 (8)	0.0562 (10)	0.0010 (7)	0.0018 (9)	0.0059 (7)
C10A	0.0763 (13)	0.0325 (7)	0.0738 (11)	−0.0008 (7)	0.0185 (10)	0.0026 (7)
C2A	0.1048 (18)	0.0537 (11)	0.0846 (14)	0.0204 (10)	−0.0177 (12)	0.0118 (10)
C12A	0.0846 (14)	0.0530 (10)	0.0762 (12)	0.0200 (9)	0.0180 (11)	0.0194 (9)
C1A	0.1165 (19)	0.0727 (13)	0.0917 (15)	−0.0048 (12)	0.0447 (15)	0.0214 (12)

O2B—C4B	1.348 (2)	O5A—C11A	1.3542 (17)
O2B—C3B	1.433 (2)	O5A—C8A	1.3851 (18)
O5B—C11B	1.351 (2)	O2A—C4A	1.3662 (18)
O5B—C8B	1.3914 (17)	O2A—C3A	1.425 (2)
O1B—C6B	1.354 (2)	O3A—C4A	1.1985 (19)
O1B—C3B	1.428 (2)	C5A—C7A	1.358 (2)
C5B—C7B	1.358 (2)	C5A—C4A	1.452 (2)
C5B—C6B	1.460 (2)	C5A—C6A	1.467 (2)
C5B—C4B	1.467 (2)	O1A—C6A	1.3545 (19)
O3B—C4B	1.2070 (19)	O1A—C3A	1.431 (2)
O4B—C6B	1.202 (2)	C8A—C9A	1.364 (2)
C7B—C8B	1.408 (2)	C8A—C7A	1.4056 (19)
C7B—H7BA	0.9300	C7A—H7AA	0.9300
C8B—C9B	1.366 (2)	C6A—O4A	1.194 (2)
C9B—C10B	1.391 (2)	C11A—C10A	1.344 (3)
C9B—H9BA	0.9300	C11A—C12A	1.481 (2)
C3B—C2B	1.499 (3)	C9A—C10A	1.399 (2)
C3B—C1B	1.502 (2)	C9A—H9AA	0.9300
C11B—C10B	1.354 (2)	C3A—C1A	1.491 (3)
C11B—C12B	1.480 (2)	C3A—C2A	1.514 (2)
C10B—H10A	0.9300	C10A—H10B	0.9300
C1B—H1BA	0.9600	C2A—H2AA	0.9600
C1B—H1BB	0.9600	C2A—H2AB	0.9600
C1B—H1BC	0.9600	C2A—H2AC	0.9600
C2B—H2BA	0.9600	C12A—H12D	0.9600
C2B—H2BB	0.9600	C12A—H12E	0.9600
C2B—H2BC	0.9600	C12A—H12F	0.9600
C12B—H12A	0.9600	C1A—H1AA	0.9600
C12B—H12B	0.9600	C1A—H1AB	0.9600
C12B—H12C	0.9600	C1A—H1AC	0.9600
C4B—O2B—C3B	118.43 (13)	C11A—O5A—C8A	107.77 (13)
C11B—O5B—C8B	107.37 (13)	C4A—O2A—C3A	118.26 (13)
C6B—O1B—C3B	119.91 (13)	C7A—C5A—C4A	125.38 (14)
C7B—C5B—C6B	124.95 (15)	C7A—C5A—C6A	115.42 (15)
C7B—C5B—C4B	116.48 (14)	C4A—C5A—C6A	119.16 (13)
C6B—C5B—C4B	118.43 (15)	C6A—O1A—C3A	119.26 (12)
O4B—C6B—O1B	116.99 (15)	C9A—C8A—O5A	108.02 (13)
O4B—C6B—C5B	126.11 (16)	C9A—C8A—C7A	139.38 (15)
O1B—C6B—C5B	116.81 (14)	O5A—C8A—C7A	112.60 (13)
C5B—C7B—C8B	133.72 (14)	C5A—C7A—C8A	134.05 (16)
C5B—C7B—H7BA	113.1	C5A—C7A—H7AA	113.0
C8B—C7B—H7BA	113.1	C8A—C7A—H7AA	113.0
O3B—C4B—O2B	118.18 (16)	O3A—C4A—O2A	117.16 (15)
O3B—C4B—C5B	124.96 (16)	O3A—C4A—C5A	126.53 (14)
O2B—C4B—C5B	116.81 (14)	O2A—C4A—C5A	116.19 (13)
C9B—C8B—O5B	107.91 (15)	O4A—C6A—O1A	117.49 (15)
C9B—C8B—C7B	138.86 (15)	O4A—C6A—C5A	125.89 (14)
O5B—C8B—C7B	113.20 (13)	O1A—C6A—C5A	116.55 (15)
C8B—C9B—C10B	107.48 (16)	C10A—C11A—O5A	109.20 (14)
C8B—C9B—H9BA	126.3	C10A—C11A—C12A	133.71 (15)
C10B—C9B—H9BA	126.3	O5A—C11A—C12A	117.09 (16)
O1B—C3B—O2B	110.13 (13)	C8A—C9A—C10A	106.92 (16)
O1B—C3B—C2B	110.27 (16)	C8A—C9A—H9AA	126.5
O2B—C3B—C2B	109.85 (15)	C10A—C9A—H9AA	126.5
O1B—C3B—C1B	105.73 (14)	O2A—C3A—O1A	109.72 (13)
O2B—C3B—C1B	106.35 (16)	O2A—C3A—C1A	110.21 (15)
C2B—C3B—C1B	114.36 (16)	O1A—C3A—C1A	110.72 (17)
O5B—C11B—C10B	109.69 (15)	O2A—C3A—C2A	106.18 (16)
O5B—C11B—C12B	116.80 (16)	O1A—C3A—C2A	105.14 (14)
C10B—C11B—C12B	133.51 (18)	C1A—C3A—C2A	114.63 (17)
C11B—C10B—C9B	107.55 (17)	C11A—C10A—C9A	108.08 (15)
C11B—C10B—H10A	126.2	C11A—C10A—H10B	126.0
C9B—C10B—H10A	126.2	C9A—C10A—H10B	126.0
C3B—C1B—H1BA	109.5	C3A—C2A—H2AA	109.5
C3B—C1B—H1BB	109.5	C3A—C2A—H2AB	109.5
H1BA—C1B—H1BB	109.5	H2AA—C2A—H2AB	109.5
C3B—C1B—H1BC	109.5	C3A—C2A—H2AC	109.5
H1BA—C1B—H1BC	109.5	H2AA—C2A—H2AC	109.5
H1BB—C1B—H1BC	109.5	H2AB—C2A—H2AC	109.5
C3B—C2B—H2BA	109.5	C11A—C12A—H12D	109.5
C3B—C2B—H2BB	109.5	C11A—C12A—H12E	109.5
H2BA—C2B—H2BB	109.5	H12D—C12A—H12E	109.5
C3B—C2B—H2BC	109.5	C11A—C12A—H12F	109.5
H2BA—C2B—H2BC	109.5	H12D—C12A—H12F	109.5
H2BB—C2B—H2BC	109.5	H12E—C12A—H12F	109.5
C11B—C12B—H12A	109.5	C3A—C1A—H1AA	109.5
C11B—C12B—H12B	109.5	C3A—C1A—H1AB	109.5
H12A—C12B—H12B	109.5	H1AA—C1A—H1AB	109.5
C11B—C12B—H12C	109.5	C3A—C1A—H1AC	109.5
H12A—C12B—H12C	109.5	H1AA—C1A—H1AC	109.5
H12B—C12B—H12C	109.5	H1AB—C1A—H1AC	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C1B—H1BC···O3Bi	0.96	2.48	3.434 (3)	170
C10B—H10A···O4Aii	0.93	2.60	3.448 (3)	153
C10A—H10B···O1Aiii	0.93	2.44	3.343 (2)	163
C2A—H2AB···O2Aiv	0.96	2.57	3.524 (3)	170
C1A—H1AA···O3B	0.96	2.55	3.496 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1B—H1BC⋯O3Bi	0.96	2.48	3.434 (3)	170
C10B—H10A⋯O4Aii	0.93	2.60	3.448 (3)	153
C10A—H10B⋯O1Aiii	0.93	2.44	3.343 (2)	163
C2A—H2AB⋯O2Aiv	0.96	2.57	3.524 (3)	170
C1A—H1AA⋯O3B	0.96	2.55	3.496 (3)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .