Dimethyl 2-(4-methyl-benzyl-idene)malonate.

In the mol-ecule of the title compound, C13H14O4, the benzene ring forms dihedral angles of 18.60 (7) and 81.36 (8)° with the two arms of the malonate moiety. The crystal structure features C-H⋯O inter-actions, which form chains running parallel to the b axis.

Related literature

For the biological activity and synthesis of alkyl­idene and aryl­idene malonates, see: Liu et al. (2012 ▶); Heydri & Tahamipour (2011 ▶); Xu & Wang (2011 ▶); Li et al. (2010 ▶, 2011 ▶); Gallier et al. (2009 ▶); Besavaiah et al. (2004 ▶). For the structures of related compounds, see: Rappoport & Gazit (1986 ▶)

Experimental

Crystal data

C13H14O4

M = 234.24

Monoclinic,

a = 14.0516 (6) Å

b = 7.7446 (3) Å

c = 12.5113 (5) Å

β = 113.727 (1)°

V = 1246.44 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.55 × 0.36 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.951, T max = 0.985

7125 measured reflections

2316 independent reflections

1850 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.08

2316 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012464/rz5063sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012464/rz5063Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012464/rz5063Isup3.cml

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

C13H14O4	F(000) = 496
Mr = 234.24	Dx = 1.248 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2372 reflections
a = 14.0516 (6) Å	θ = 3.1–26.3°
b = 7.7446 (3) Å	µ = 0.09 mm−1
c = 12.5113 (5) Å	T = 273 K
β = 113.727 (1)°	Block, colourless
V = 1246.44 (9) Å3	0.55 × 0.36 × 0.16 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2316 independent reflections
Radiation source: fine-focus sealed tube	1850 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→11
Tmin = 0.951, Tmax = 0.985	k = −9→9
7125 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.2125P] where P = (Fo2 + 2Fc2)/3
2316 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.17 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	0.15387 (12)	−0.05063 (19)	0.26275 (14)	0.0835 (5)
O2	0.03912 (10)	0.15029 (16)	0.16332 (11)	0.0631 (4)
O3	0.10137 (11)	0.30017 (18)	−0.02578 (11)	0.0775 (5)
O4	0.19102 (10)	0.45753 (15)	0.13086 (11)	0.0621 (4)
C1	0.36456 (14)	0.2423 (2)	0.04658 (15)	0.0594 (5)
H1A	0.2996	0.2897	0.0027	0.071*
C2	0.44558 (15)	0.2730 (2)	0.01473 (16)	0.0635 (5)
H2A	0.4340	0.3405	−0.0508	0.076*
C3	0.54418 (14)	0.2067 (2)	0.07690 (16)	0.0589 (5)
C4	0.55784 (15)	0.1057 (3)	0.17338 (17)	0.0649 (5)
H4A	0.6230	0.0592	0.2172	0.078*
C5	0.47681 (15)	0.0728 (2)	0.20574 (16)	0.0607 (5)
H5A	0.4883	0.0034	0.2704	0.073*
C6	0.37811 (13)	0.1409 (2)	0.14407 (14)	0.0521 (4)
C7	0.29555 (14)	0.0931 (2)	0.18075 (14)	0.0540 (4)
H7A	0.3116	0.0001	0.2321	0.065*
C8	0.20104 (13)	0.1592 (2)	0.15361 (14)	0.0517 (4)
C9	0.13063 (14)	0.0737 (2)	0.20022 (15)	0.0555 (4)
C10	−0.03757 (16)	0.0739 (3)	0.19883 (19)	0.0683 (5)
H10A	−0.1005	0.1405	0.1677	0.103*
H10B	−0.0114	0.0726	0.2825	0.103*
H10C	−0.0517	−0.0422	0.1698	0.103*
C11	0.15819 (13)	0.3100 (2)	0.07484 (14)	0.0512 (4)
C12	0.15580 (17)	0.6132 (2)	0.0614 (2)	0.0775 (6)
H12A	0.1839	0.7125	0.1098	0.116*
H12B	0.0813	0.6181	0.0295	0.116*
H12C	0.1790	0.6120	−0.0011	0.116*
C13	0.63181 (16)	0.2386 (3)	0.03988 (19)	0.0766 (6)
H13A	0.6081	0.3113	−0.0280	0.115*
H13B	0.6554	0.1305	0.0219	0.115*
H13C	0.6880	0.2943	0.1021	0.115*

	U11	U22	U33	U12	U13	U23
O1	0.0768 (10)	0.0778 (10)	0.1055 (11)	0.0191 (8)	0.0467 (8)	0.0389 (8)
O2	0.0565 (8)	0.0567 (7)	0.0771 (8)	0.0059 (6)	0.0280 (6)	0.0078 (6)
O3	0.0810 (10)	0.0704 (9)	0.0579 (8)	0.0043 (7)	0.0039 (7)	0.0042 (6)
O4	0.0622 (8)	0.0465 (7)	0.0703 (8)	0.0023 (6)	0.0191 (6)	0.0000 (5)
C1	0.0510 (10)	0.0607 (11)	0.0617 (10)	0.0083 (8)	0.0176 (8)	0.0066 (8)
C2	0.0654 (12)	0.0638 (12)	0.0616 (10)	0.0018 (9)	0.0260 (9)	0.0032 (9)
C3	0.0556 (10)	0.0563 (10)	0.0629 (10)	−0.0051 (8)	0.0218 (8)	−0.0171 (8)
C4	0.0476 (10)	0.0688 (12)	0.0669 (11)	0.0076 (9)	0.0111 (8)	−0.0072 (9)
C5	0.0561 (11)	0.0598 (11)	0.0582 (10)	0.0083 (9)	0.0148 (8)	0.0043 (8)
C6	0.0517 (10)	0.0460 (9)	0.0531 (9)	0.0034 (7)	0.0154 (7)	−0.0030 (7)
C7	0.0561 (11)	0.0482 (9)	0.0529 (9)	0.0039 (8)	0.0169 (8)	0.0051 (7)
C8	0.0525 (10)	0.0454 (9)	0.0524 (9)	0.0017 (7)	0.0161 (7)	−0.0002 (7)
C9	0.0584 (11)	0.0488 (10)	0.0579 (10)	0.0051 (8)	0.0220 (8)	0.0023 (8)
C10	0.0605 (11)	0.0678 (12)	0.0826 (13)	−0.0028 (10)	0.0349 (10)	−0.0023 (10)
C11	0.0438 (9)	0.0518 (10)	0.0551 (9)	0.0020 (7)	0.0170 (7)	0.0010 (7)
C12	0.0783 (14)	0.0483 (11)	0.1068 (16)	0.0099 (10)	0.0383 (13)	0.0147 (10)
C13	0.0645 (12)	0.0831 (14)	0.0874 (14)	−0.0078 (11)	0.0359 (11)	−0.0216 (11)

O1—C9	1.200 (2)	C5—H5A	0.9300
O2—C9	1.319 (2)	C6—C7	1.457 (2)
O2—C10	1.447 (2)	C7—C8	1.334 (2)
O3—C11	1.1913 (19)	C7—H7A	0.9300
O4—C11	1.3226 (19)	C8—C11	1.490 (2)
O4—C12	1.452 (2)	C8—C9	1.491 (2)
C1—C2	1.370 (3)	C10—H10A	0.9600
C1—C6	1.398 (2)	C10—H10B	0.9600
C1—H1A	0.9300	C10—H10C	0.9600
C2—C3	1.386 (3)	C12—H12A	0.9600
C2—H2A	0.9300	C12—H12B	0.9600
C3—C4	1.385 (3)	C12—H12C	0.9600
C3—C13	1.500 (3)	C13—H13A	0.9600
C4—C5	1.377 (3)	C13—H13B	0.9600
C4—H4A	0.9300	C13—H13C	0.9600
C5—C6	1.391 (2)
C9—O2—C10	116.73 (15)	C11—C8—C9	116.87 (15)
C11—O4—C12	115.97 (14)	O1—C9—O2	124.07 (17)
C2—C1—C6	120.92 (16)	O1—C9—C8	124.21 (16)
C2—C1—H1A	119.5	O2—C9—C8	111.71 (15)
C6—C1—H1A	119.5	O2—C10—H10A	109.5
C1—C2—C3	122.19 (18)	O2—C10—H10B	109.5
C1—C2—H2A	118.9	H10A—C10—H10B	109.5
C3—C2—H2A	118.9	O2—C10—H10C	109.5
C4—C3—C2	117.06 (18)	H10A—C10—H10C	109.5
C4—C3—C13	121.26 (18)	H10B—C10—H10C	109.5
C2—C3—C13	121.67 (18)	O3—C11—O4	123.90 (16)
C5—C4—C3	121.31 (17)	O3—C11—C8	124.73 (16)
C5—C4—H4A	119.3	O4—C11—C8	111.37 (14)
C3—C4—H4A	119.3	O4—C12—H12A	109.5
C4—C5—C6	121.63 (18)	O4—C12—H12B	109.5
C4—C5—H5A	119.2	H12A—C12—H12B	109.5
C6—C5—H5A	119.2	O4—C12—H12C	109.5
C5—C6—C1	116.89 (17)	H12A—C12—H12C	109.5
C5—C6—C7	118.11 (16)	H12B—C12—H12C	109.5
C1—C6—C7	124.87 (15)	C3—C13—H13A	109.5
C8—C7—C6	131.27 (16)	C3—C13—H13B	109.5
C8—C7—H7A	114.4	H13A—C13—H13B	109.5
C6—C7—H7A	114.4	C3—C13—H13C	109.5
C7—C8—C11	124.44 (16)	H13A—C13—H13C	109.5
C7—C8—C9	118.63 (15)	H13B—C13—H13C	109.5
C6—C1—C2—C3	−0.3 (3)	C6—C7—C8—C9	176.17 (16)
C1—C2—C3—C4	0.5 (3)	C10—O2—C9—O1	−2.0 (3)
C1—C2—C3—C13	178.91 (17)	C10—O2—C9—C8	177.38 (14)
C2—C3—C4—C5	0.1 (3)	C7—C8—C9—O1	1.2 (3)
C13—C3—C4—C5	−178.38 (17)	C11—C8—C9—O1	178.61 (17)
C3—C4—C5—C6	−0.8 (3)	C7—C8—C9—O2	−178.12 (15)
C4—C5—C6—C1	0.9 (3)	C11—C8—C9—O2	−0.7 (2)
C4—C5—C6—C7	177.10 (16)	C12—O4—C11—O3	−1.6 (3)
C2—C1—C6—C5	−0.4 (3)	C12—O4—C11—C8	178.58 (14)
C2—C1—C6—C7	−176.28 (17)	C7—C8—C11—O3	98.3 (2)
C5—C6—C7—C8	166.38 (18)	C9—C8—C11—O3	−78.9 (2)
C1—C6—C7—C8	−17.8 (3)	C7—C8—C11—O4	−81.9 (2)
C6—C7—C8—C11	−1.0 (3)	C9—C8—C11—O4	100.88 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O1i	0.96	2.49	3.442 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13C⋯O1i	0.96	2.49	3.442 (3)	170

Symmetry code: (i) .