(4-Cyano-phen-yl)methyl-ene diacetate.

In the title mol-ecule, C(12)H(11)NO(4), the two acetyl groups are inclined by 71.3 (1) and 46.2 (1)° to the benzene ring. In the crystal structure, mol-ecules are linked into a chain along the c axis by C-H⋯O hydrogen bonds.

Related literature

For general background on nitrile compounds, see: Jin et al. (1994 ▶); Radl et al. (2000 ▶). For a related structure, see: Fu & Zhao (2007 ▶).

Experimental

Crystal data

C12H11NO4

M = 233.22

Monoclinic,

a = 8.1389 (15) Å

b = 20.919 (3) Å

c = 7.7748 (10) Å

β = 115.531 (7)°

V = 1194.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.35 × 0.30 × 0.30 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.951, T max = 0.968

11568 measured reflections

2723 independent reflections

2096 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.163

S = 1.11

2723 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012543/ci2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012543/ci2587Isup2.hkl

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

C12H11NO4	F000 = 488
Mr = 233.22	Dx = 1.297 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2461 reflections
a = 8.1389 (15) Å	θ = 3.1–27.5º
b = 20.919 (3) Å	µ = 0.10 mm−1
c = 7.7748 (10) Å	T = 293 (2) K
β = 115.531 (7)º	Block, colourless
V = 1194.5 (3) Å3	0.35 × 0.30 × 0.30 mm
Z = 4

Rigaku Mercury2 diffractometer	2723 independent reflections
Radiation source: fine-focus sealed tube	2096 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −10→10
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −27→27
Tmin = 0.951, Tmax = 0.968	l = −10→10
11568 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.2026P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
2723 reflections	Δρmax = 0.20 e Å−3
156 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.4962 (2)	0.34433 (9)	0.7629 (3)	0.0477 (4)
H1	0.5242	0.2985	0.7757	0.057*
C2	0.6526 (2)	0.38246 (9)	0.7624 (2)	0.0462 (4)
C3	0.8165 (3)	0.35208 (10)	0.8026 (3)	0.0586 (5)
H3	0.8287	0.3086	0.8300	0.070*
C4	0.9621 (3)	0.38610 (11)	0.8021 (3)	0.0626 (5)
H4	1.0722	0.3656	0.8301	0.075*
C5	0.9433 (3)	0.45058 (10)	0.7598 (3)	0.0565 (5)
C6	0.7805 (3)	0.48137 (11)	0.7208 (4)	0.0693 (6)
H6	0.7685	0.5249	0.6936	0.083*
C7	0.6354 (3)	0.44710 (10)	0.7223 (3)	0.0627 (5)
H7	0.5260	0.4677	0.6962	0.075*
C8	1.0936 (3)	0.48634 (12)	0.7541 (4)	0.0701 (6)
C9	0.5275 (3)	0.33307 (10)	1.0797 (3)	0.0535 (5)
C10	0.4826 (4)	0.36266 (13)	1.2275 (4)	0.0779 (7)
H10A	0.5070	0.3327	1.3292	0.117*
H10B	0.3561	0.3742	1.1723	0.117*
H10C	0.5557	0.4002	1.2768	0.117*
C11	0.2023 (3)	0.31319 (10)	0.5370 (4)	0.0608 (5)
C12	0.0457 (3)	0.33230 (13)	0.3577 (4)	0.0799 (7)
H12A	−0.0238	0.2951	0.2961	0.120*
H12B	0.0895	0.3526	0.2747	0.120*
H12C	−0.0300	0.3616	0.3860	0.120*
N1	1.2104 (3)	0.51476 (12)	0.7475 (4)	0.0967 (8)
O1	0.45266 (18)	0.36634 (6)	0.91409 (19)	0.0536 (4)
O2	0.6196 (2)	0.28659 (9)	1.0993 (2)	0.0757 (5)
O3	0.33842 (17)	0.35734 (6)	0.59147 (18)	0.0545 (4)
O4	0.2134 (2)	0.26588 (8)	0.6276 (3)	0.0905 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0498 (10)	0.0476 (9)	0.0466 (9)	0.0048 (8)	0.0217 (8)	0.0008 (7)
C2	0.0465 (9)	0.0503 (10)	0.0406 (9)	0.0022 (8)	0.0178 (7)	−0.0018 (7)
C3	0.0548 (11)	0.0518 (11)	0.0689 (13)	0.0068 (9)	0.0266 (10)	0.0037 (9)
C4	0.0480 (11)	0.0687 (13)	0.0728 (14)	0.0092 (9)	0.0277 (10)	0.0020 (10)
C5	0.0496 (10)	0.0654 (12)	0.0553 (11)	−0.0037 (9)	0.0234 (9)	−0.0012 (9)
C6	0.0612 (13)	0.0515 (11)	0.0986 (18)	−0.0007 (10)	0.0377 (13)	0.0069 (11)
C7	0.0524 (11)	0.0526 (11)	0.0866 (15)	0.0078 (9)	0.0333 (11)	0.0069 (10)
C8	0.0574 (13)	0.0760 (15)	0.0783 (16)	−0.0037 (11)	0.0304 (11)	0.0028 (12)
C9	0.0505 (10)	0.0609 (12)	0.0505 (11)	−0.0104 (9)	0.0230 (9)	0.0027 (9)
C10	0.0912 (17)	0.0936 (18)	0.0642 (14)	−0.0232 (14)	0.0478 (13)	−0.0149 (12)
C11	0.0513 (11)	0.0548 (11)	0.0786 (14)	−0.0018 (9)	0.0303 (10)	−0.0020 (10)
C12	0.0525 (12)	0.0849 (16)	0.0844 (17)	−0.0072 (11)	0.0126 (11)	−0.0059 (13)
N1	0.0668 (14)	0.0997 (17)	0.129 (2)	−0.0114 (12)	0.0470 (14)	0.0127 (15)
O1	0.0614 (8)	0.0528 (7)	0.0533 (8)	0.0088 (6)	0.0310 (6)	0.0040 (6)
O2	0.0770 (11)	0.0842 (11)	0.0665 (10)	0.0217 (9)	0.0315 (8)	0.0249 (8)
O3	0.0500 (7)	0.0556 (8)	0.0513 (8)	−0.0048 (6)	0.0158 (6)	0.0033 (6)
O4	0.0642 (10)	0.0731 (11)	0.1270 (16)	−0.0078 (8)	0.0344 (10)	0.0250 (11)

C1—O3	1.423 (2)	C7—H7	0.93
C1—O1	1.441 (2)	C8—N1	1.141 (3)
C1—C2	1.504 (3)	C9—O2	1.197 (3)
C1—H1	0.98	C9—O1	1.355 (2)
C2—C7	1.381 (3)	C9—C10	1.483 (3)
C2—C3	1.386 (3)	C10—H10A	0.96
C3—C4	1.384 (3)	C10—H10B	0.96
C3—H3	0.93	C10—H10C	0.96
C4—C5	1.381 (3)	C11—O4	1.196 (3)
C4—H4	0.93	C11—O3	1.362 (2)
C5—C6	1.384 (3)	C11—C12	1.482 (3)
C5—C8	1.451 (3)	C12—H12A	0.96
C6—C7	1.386 (3)	C12—H12B	0.96
C6—H6	0.93	C12—H12C	0.96
O3—C1—O1	105.26 (14)	C6—C7—H7	119.8
O3—C1—C2	108.62 (14)	N1—C8—C5	179.2 (3)
O1—C1—C2	109.80 (14)	O2—C9—O1	122.60 (18)
O3—C1—H1	111.0	O2—C9—C10	126.2 (2)
O1—C1—H1	111.0	O1—C9—C10	111.2 (2)
C2—C1—H1	111.0	C9—C10—H10A	109.5
C7—C2—C3	119.60 (18)	C9—C10—H10B	109.5
C7—C2—C1	121.08 (17)	H10A—C10—H10B	109.5
C3—C2—C1	119.32 (16)	C9—C10—H10C	109.5
C4—C3—C2	120.36 (19)	H10A—C10—H10C	109.5
C4—C3—H3	119.8	H10B—C10—H10C	109.5
C2—C3—H3	119.8	O4—C11—O3	122.2 (2)
C5—C4—C3	119.73 (19)	O4—C11—C12	126.4 (2)
C5—C4—H4	120.1	O3—C11—C12	111.37 (19)
C3—C4—H4	120.1	C11—C12—H12A	109.5
C4—C5—C6	120.28 (19)	C11—C12—H12B	109.5
C4—C5—C8	120.14 (19)	H12A—C12—H12B	109.5
C6—C5—C8	119.6 (2)	C11—C12—H12C	109.5
C5—C6—C7	119.7 (2)	H12A—C12—H12C	109.5
C5—C6—H6	120.1	H12B—C12—H12C	109.5
C7—C6—H6	120.1	C9—O1—C1	116.28 (15)
C2—C7—C6	120.30 (19)	C11—O3—C1	116.52 (15)
C2—C7—H7	119.8

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2i	0.98	2.56	3.351 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2i	0.98	2.56	3.351 (3)	137

Symmetry code: (i) .