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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o986.
Published online 2008 May 3. doi:  10.1107/S1600536808012543
PMCID: PMC2961459

(4-Cyano­phen­yl)methyl­ene diacetate

Abstract

In the title mol­ecule, C12H11NO4, the two acetyl groups are inclined by 71.3 (1) and 46.2 (1)° to the benzene ring. In the crystal structure, mol­ecules 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 [triangle]); Radl et al. (2000 [triangle]). For a related structure, see: Fu & Zhao (2007 [triangle]).

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Object name is e-64-0o986-scheme1.jpg

Experimental

Crystal data

  • C12H11NO4
  • M r = 233.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o986-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

Nitrile compounds are used extensively in the chemical industry. They are discharged into the environment in industrial waste water, agricultural chemicals, etc. Nitrile derivatives are important materials in the synthesis of some heterocyclic molecules (Radl et al., 2000), and they have been used as starting materials for phthalocyanines (Jin et al., 1994). Recently, we have reported the crystal structure of a benzonitrile compound (Fu et al., 2007). The title compound was unexpectedly obtained during our work on the nitrile compounds. Herein we report its crystal structure.

The bond lengths and angles have normal values. The O1/O2/C9/C10 and O3/O4/C11/C12 planes form dihedral angles of 71.3 (1)° and 46.2 (1)°, respectively, with the C2—C7 plane. The molecules are linked into a chain along the c axis by C—H···O hydrogen bonds (Table 1).

Experimental

4-Formylbenzonitrile (0.262 mg, 2 mmol) was dissolved in acetic anhydride (5 ml) and heated under reflux for 3 h. The mixture was cooled to room temperature and the solution was filtered. The solvent was removed under vacuum from the filtrate to obtain a white precipitate of the title compound (yield 88%). Colourless crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol (15 ml) solution of the compound (100 mg) after 4 d.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2–1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C12H11NO4F000 = 488
Mr = 233.22Dx = 1.297 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2461 reflections
a = 8.1389 (15) Åθ = 3.1–27.5º
b = 20.919 (3) ŵ = 0.10 mm1
c = 7.7748 (10) ÅT = 293 (2) K
β = 115.531 (7)ºBlock, colourless
V = 1194.5 (3) Å30.35 × 0.30 × 0.30 mm
Z = 4

Data collection

Rigaku Mercury2 diffractometer2723 independent reflections
Radiation source: fine-focus sealed tube2096 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.1º
ω scansh = −10→10
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −27→27
Tmin = 0.951, Tmax = 0.968l = −10→10
11568 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-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 reflectionsΔρmax = 0.20 e Å3
156 parametersΔρmin = −0.17 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.4962 (2)0.34433 (9)0.7629 (3)0.0477 (4)
H10.52420.29850.77570.057*
C20.6526 (2)0.38246 (9)0.7624 (2)0.0462 (4)
C30.8165 (3)0.35208 (10)0.8026 (3)0.0586 (5)
H30.82870.30860.83000.070*
C40.9621 (3)0.38610 (11)0.8021 (3)0.0626 (5)
H41.07220.36560.83010.075*
C50.9433 (3)0.45058 (10)0.7598 (3)0.0565 (5)
C60.7805 (3)0.48137 (11)0.7208 (4)0.0693 (6)
H60.76850.52490.69360.083*
C70.6354 (3)0.44710 (10)0.7223 (3)0.0627 (5)
H70.52600.46770.69620.075*
C81.0936 (3)0.48634 (12)0.7541 (4)0.0701 (6)
C90.5275 (3)0.33307 (10)1.0797 (3)0.0535 (5)
C100.4826 (4)0.36266 (13)1.2275 (4)0.0779 (7)
H10A0.50700.33271.32920.117*
H10B0.35610.37421.17230.117*
H10C0.55570.40021.27680.117*
C110.2023 (3)0.31319 (10)0.5370 (4)0.0608 (5)
C120.0457 (3)0.33230 (13)0.3577 (4)0.0799 (7)
H12A−0.02380.29510.29610.120*
H12B0.08950.35260.27470.120*
H12C−0.03000.36160.38600.120*
N11.2104 (3)0.51476 (12)0.7475 (4)0.0967 (8)
O10.45266 (18)0.36634 (6)0.91409 (19)0.0536 (4)
O20.6196 (2)0.28659 (9)1.0993 (2)0.0757 (5)
O30.33842 (17)0.35734 (6)0.59147 (18)0.0545 (4)
O40.2134 (2)0.26588 (8)0.6276 (3)0.0905 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0498 (10)0.0476 (9)0.0466 (9)0.0048 (8)0.0217 (8)0.0008 (7)
C20.0465 (9)0.0503 (10)0.0406 (9)0.0022 (8)0.0178 (7)−0.0018 (7)
C30.0548 (11)0.0518 (11)0.0689 (13)0.0068 (9)0.0266 (10)0.0037 (9)
C40.0480 (11)0.0687 (13)0.0728 (14)0.0092 (9)0.0277 (10)0.0020 (10)
C50.0496 (10)0.0654 (12)0.0553 (11)−0.0037 (9)0.0234 (9)−0.0012 (9)
C60.0612 (13)0.0515 (11)0.0986 (18)−0.0007 (10)0.0377 (13)0.0069 (11)
C70.0524 (11)0.0526 (11)0.0866 (15)0.0078 (9)0.0333 (11)0.0069 (10)
C80.0574 (13)0.0760 (15)0.0783 (16)−0.0037 (11)0.0304 (11)0.0028 (12)
C90.0505 (10)0.0609 (12)0.0505 (11)−0.0104 (9)0.0230 (9)0.0027 (9)
C100.0912 (17)0.0936 (18)0.0642 (14)−0.0232 (14)0.0478 (13)−0.0149 (12)
C110.0513 (11)0.0548 (11)0.0786 (14)−0.0018 (9)0.0303 (10)−0.0020 (10)
C120.0525 (12)0.0849 (16)0.0844 (17)−0.0072 (11)0.0126 (11)−0.0059 (13)
N10.0668 (14)0.0997 (17)0.129 (2)−0.0114 (12)0.0470 (14)0.0127 (15)
O10.0614 (8)0.0528 (7)0.0533 (8)0.0088 (6)0.0310 (6)0.0040 (6)
O20.0770 (11)0.0842 (11)0.0665 (10)0.0217 (9)0.0315 (8)0.0249 (8)
O30.0500 (7)0.0556 (8)0.0513 (8)−0.0048 (6)0.0158 (6)0.0033 (6)
O40.0642 (10)0.0731 (11)0.1270 (16)−0.0078 (8)0.0344 (10)0.0250 (11)

Geometric parameters (Å, °)

C1—O31.423 (2)C7—H70.93
C1—O11.441 (2)C8—N11.141 (3)
C1—C21.504 (3)C9—O21.197 (3)
C1—H10.98C9—O11.355 (2)
C2—C71.381 (3)C9—C101.483 (3)
C2—C31.386 (3)C10—H10A0.96
C3—C41.384 (3)C10—H10B0.96
C3—H30.93C10—H10C0.96
C4—C51.381 (3)C11—O41.196 (3)
C4—H40.93C11—O31.362 (2)
C5—C61.384 (3)C11—C121.482 (3)
C5—C81.451 (3)C12—H12A0.96
C6—C71.386 (3)C12—H12B0.96
C6—H60.93C12—H12C0.96
O3—C1—O1105.26 (14)C6—C7—H7119.8
O3—C1—C2108.62 (14)N1—C8—C5179.2 (3)
O1—C1—C2109.80 (14)O2—C9—O1122.60 (18)
O3—C1—H1111.0O2—C9—C10126.2 (2)
O1—C1—H1111.0O1—C9—C10111.2 (2)
C2—C1—H1111.0C9—C10—H10A109.5
C7—C2—C3119.60 (18)C9—C10—H10B109.5
C7—C2—C1121.08 (17)H10A—C10—H10B109.5
C3—C2—C1119.32 (16)C9—C10—H10C109.5
C4—C3—C2120.36 (19)H10A—C10—H10C109.5
C4—C3—H3119.8H10B—C10—H10C109.5
C2—C3—H3119.8O4—C11—O3122.2 (2)
C5—C4—C3119.73 (19)O4—C11—C12126.4 (2)
C5—C4—H4120.1O3—C11—C12111.37 (19)
C3—C4—H4120.1C11—C12—H12A109.5
C4—C5—C6120.28 (19)C11—C12—H12B109.5
C4—C5—C8120.14 (19)H12A—C12—H12B109.5
C6—C5—C8119.6 (2)C11—C12—H12C109.5
C5—C6—C7119.7 (2)H12A—C12—H12C109.5
C5—C6—H6120.1H12B—C12—H12C109.5
C7—C6—H6120.1C9—O1—C1116.28 (15)
C2—C7—C6120.30 (19)C11—O3—C1116.52 (15)
C2—C7—H7119.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.982.563.351 (3)137

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2587).

References

  • Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.
  • Jin, Z., Nolan, K., McArthur, C. R., Lever, A. B. P. & Leznoff, C. C. (1994). J. Organomet. Chem.468, 205–212.
  • Radl, S., Hezky, P., Konvicka, P. & Krejgi, J. (2000). Collect. Czech. Chem. Commun.65, 1093–1108.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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