Dimethyl 2,2-bis-(2-cyano-ethyl)malonate.

The asymmetric unit of the title compound, C(11)H(14)N(2)O(4), contains one half-mol-ecule; a twofold rotation axis passes through the central C atom. Inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into a one-dimensional supra-molecular structure.

Related literature

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

Experimental

Crystal data

C11H14N2O4

M = 238.24

Monoclinic,

a = 13.071 (3) Å

b = 8.5060 (17) Å

c = 10.914 (2) Å

β = 90.55 (3)°

V = 1213.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.961, T max = 0.975

1140 measured reflections

1091 independent reflections

860 reflections with I > 2σ(I)

R int = 0.048

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.155

S = 0.99

1091 reflections

78 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 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/S1600536808005850/rk2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005850/rk2080Isup2.hkl

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

C11H14N2O4	F000 = 504
Mr = 238.24	Dx = 1.304 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 13.071 (3) Å	θ = 10–14º
b = 8.5060 (17) Å	µ = 0.10 mm−1
c = 10.914 (2) Å	T = 293 (2) K
β = 90.55 (3)º	Block, colourless
V = 1213.4 (4) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.048
Radiation source: Fine–focus sealed tube	θmax = 25.2º
Monochromator: Graphite	θmin = 2.9º
T = 293(2) K	h = −15→15
ω/2θ scans	k = 0→10
Absorption correction: ψ scan(North et al., 1968)	l = 0→12
Tmin = 0.961, Tmax = 0.975	3 standard reflections
1140 measured reflections	every 200 reflections
1091 independent reflections	intensity decay: none
860 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.065	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0591P)2 + 3.2284P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
1091 reflections	Δρmax = 0.21 e Å−3
78 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: Direct	Extinction correction: None

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 RR–factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	−0.1143 (3)	0.5595 (3)	0.4119 (3)	0.0730 (10)
C1	−0.1098 (2)	0.6248 (3)	0.5039 (3)	0.0471 (7)
O1	0.15852 (15)	1.0070 (2)	0.6705 (2)	0.0516 (6)
O2	0.09191 (13)	1.1101 (2)	0.84034 (16)	0.0402 (5)
C2	−0.1041 (3)	0.7072 (4)	0.6228 (3)	0.0589 (9)
H2A	−0.1056	0.6311	0.6890	0.071*
H2B	−0.1628	0.7760	0.6312	0.071*
C3	−0.00519 (19)	0.8043 (3)	0.6315 (2)	0.0333 (6)
H3A	−0.0013	0.8737	0.5612	0.040*
H3B	0.0532	0.7340	0.6293	0.040*
C4	0.0000	0.9032 (4)	0.7500	0.0301 (8)
C5	0.09365 (19)	1.0115 (3)	0.7444 (2)	0.0309 (6)
C6	0.1753 (2)	1.2212 (4)	0.8494 (3)	0.0481 (8)
H6A	0.1667	1.2853	0.9209	0.072*
H6B	0.1756	1.2867	0.7778	0.072*
H6C	0.2390	1.1653	0.8555	0.072*

	U11	U22	U33	U12	U13	U23
N1	0.0893 (16)	0.0651 (16)	0.0628 (19)	0.0048 (16)	−0.0436 (17)	−0.0172 (15)
C1	0.0547 (18)	0.0469 (14)	0.0532 (17)	−0.0015 (14)	−0.0192 (13)	−0.0050 (14)
O1	0.0430 (12)	0.0432 (12)	0.0585 (14)	−0.0076 (9)	0.0028 (10)	−0.0102 (10)
O2	0.0498 (10)	0.0442 (10)	0.0465 (11)	−0.0111 (8)	−0.0098 (8)	−0.0088 (8)
C2	0.0571 (18)	0.0484 (17)	0.0582 (13)	−0.0162 (16)	−0.0205 (16)	−0.0162 (15)
C3	0.0404 (14)	0.0479 (12)	0.0355 (13)	0.0018 (11)	−0.0067 (10)	−0.0007 (10)
C4	0.0476 (19)	0.0472 (16)	0.0355 (18)	−0.0017 (10)	−0.0025 (14)	0.0006 (10)
C5	0.0421 (13)	0.0469 (13)	0.0344 (13)	0.0058 (10)	−0.0093 (10)	0.0032 (10)
C6	0.0477 (17)	0.0452 (16)	0.0549 (18)	−0.0162 (14)	−0.0138 (13)	−0.0046 (13)

N1—C1	1.149 (4)	C3—H3A	0.9700
C1—C2	1.476 (4)	C3—H3B	0.9700
O1—C5	1.177 (3)	C4—C5	1.534 (3)
O2—C5	1.341 (3)	C4—C5i	1.534 (3)
O2—C6	1.445 (3)	C4—C3i	1.544 (3)
C2—C3	1.537 (4)	C6—H6A	0.9600
C2—H2A	0.9700	C6—H6B	0.9600
C2—H2B	0.9700	C6—H6C	0.9600
C3—C4	1.544 (3)
N1—C1—C2	179.4 (4)	C5—C4—C3	108.85 (13)
C5—O2—C6	116.3 (2)	C5i—C4—C3	109.39 (13)
C1—C2—C3	110.1 (3)	C5—C4—C3i	109.39 (13)
C1—C2—H2A	109.6	C5i—C4—C3i	108.85 (13)
C3—C2—H2A	109.6	C3—C4—C3i	113.9 (3)
C1—C2—H2B	109.6	O1—C5—O2	125.0 (2)
C3—C2—H2B	109.6	O1—C5—C4	126.0 (2)
H2A—C2—H2B	108.1	O2—C5—C4	108.96 (19)
C2—C3—C4	112.0 (2)	O2—C6—H6A	109.5
C2—C3—H3A	109.2	O2—C6—H6B	109.5
C4—C3—H3A	109.2	H6A—C6—H6B	109.5
C2—C3—H3B	109.2	O2—C6—H6C	109.5
C4—C3—H3B	109.2	H6A—C6—H6C	109.5
H3A—C3—H3B	107.9	H6B—C6—H6C	109.5
C5—C4—C5i	106.2 (3)
C1—C2—C3—C4	175.4 (2)	C5i—C4—C5—O1	−126.7 (3)
C2—C3—C4—C5	−173.0 (2)	C3—C4—C5—O1	−9.0 (3)
C2—C3—C4—C5i	−57.4 (3)	C3i—C4—C5—O1	116.0 (3)
C2—C3—C4—C3i	64.63 (19)	C5i—C4—C5—O2	55.37 (14)
C6—O2—C5—O1	2.0 (4)	C3—C4—C5—O2	173.02 (18)
C6—O2—C5—C4	180.0 (2)	C3i—C4—C5—O2	−61.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···N1ii	0.96	2.57	3.494 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯N1i	0.96	2.57	3.494 (5)	161

Symmetry code: (i) .