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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1436.
Published online 2008 July 9. doi:  10.1107/S1600536808020527
PMCID: PMC2962067

4,4′-(Oxydimethyl­ene)dibenzonitrile

Abstract

The title compound, C16H12N2O, was accidentally synthesized by the reaction of 4-(bromo­meth­yl)benzonitrile and penta­erythritol. The dihedral angle between the benzene rings is 57.39 (9)°. In the crystal structure, mol­ecules are linked by inter­molecular C—H(...)N hydrogen-bonding inter­actions to form chains running parallel to the b axis.

Related literature

For applications of nitrile derivatives in the synthesis of some heterocyclic mol­ecules, see: Radl et al. (2000 [triangle]); Jin et al. (1994 [triangle]). For the crystal structure of a related compound, see: Fu & Zhao (2007 [triangle]).

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Object name is e-64-o1436-scheme1.jpg

Experimental

Crystal data

  • C16H12N2O
  • M r = 248.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1436-efi1.jpg
  • a = 14.444 (3) Å
  • b = 7.6674 (13) Å
  • c = 11.897 (2) Å
  • β = 96.326 (14)°
  • V = 1309.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 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 = 0.939, T max = 0.978
  • 13064 measured reflections
  • 3007 independent reflections
  • 1498 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.149
  • S = 1.01
  • 3007 reflections
  • 172 parameters
  • H-atom parameters constrained
  • Δρmax = 0.11 e Å−3
  • Δρmin = −0.15 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/PC (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/S1600536808020527/rz2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020527/rz2229Isup2.hkl

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

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to HZ.

supplementary crystallographic information

Comment

Nitrile derivatives are an important class of compounds used in the chemical industry. For example, nitrile derivatives are employed in the synthesis of some heterocyclic molecules (Radl et al., 2000), and have been used as starting materials for the synthesis of phthalocyanines (Jin et al., 1994). Recently, we have reported the crystal structure of a benzonitrile compound (Fu & Zhao, 2007). The title compound was unexpectedly obtained during our work on nitrile compounds, and its crystal structure is reported here.

In the title compound (Fig. 1), bond lengths and angles have normal values. The planes through the C2—C7 and C10—C15 benzene rings form a dihedral angle of 57.39 (9)°. The crystal structure is stabilized by an intermolecular C—H···N hydrogen bond forming chains of molecules along the b-axis (Table 1).

Experimental

Pentaerythritol (0.136 g, 1 mmol) and 4-(bromomethyl)benzonitrile (0.658 g, 4 mmol) were dissolved in water in the presence of sodium hydroxide (0.160 g, 4 mmol) and heated under reflux for 2 days. After the mixture was cooled to room temperature, the solvent was removed in vacuum to afford a white precipitate of the title compound. Colourless crystals suitable for X-ray diffraction were obtained from a solution of 100 mg in 15 ml diethylether by slow evaporation after 5 days.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(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

C16H12N2OF000 = 520
Mr = 248.28Dx = 1.259 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1930 reflections
a = 14.444 (3) Åθ = 2.8–27.5º
b = 7.6674 (13) ŵ = 0.08 mm1
c = 11.897 (2) ÅT = 293 (2) K
β = 96.326 (14)ºBlock, colourless
V = 1309.6 (4) Å30.35 × 0.30 × 0.30 mm
Z = 4

Data collection

Rigaku Mercury2 diffractometer3007 independent reflections
Radiation source: fine-focus sealed tube1498 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.072
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 2.8º
ω scansh = −18→18
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)k = −9→9
Tmin = 0.939, Tmax = 0.978l = −15→15
13064 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)] = 0.064H-atom parameters constrained
wR(F2) = 0.149  w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3007 reflectionsΔρmax = 0.11 e Å3
172 parametersΔρmin = −0.15 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
O10.21121 (10)0.2174 (2)0.82830 (14)0.0632 (5)
C130.40291 (15)0.6678 (3)1.0392 (2)0.0543 (6)
C5−0.05516 (16)0.2145 (3)0.5362 (2)0.0530 (6)
C10.17453 (17)0.0647 (3)0.7737 (2)0.0610 (7)
H1A0.1547−0.01630.82890.073*
H1B0.22180.00820.73460.073*
C160.43912 (17)0.8289 (4)1.0896 (2)0.0647 (7)
C30.10674 (17)0.2247 (3)0.6017 (2)0.0616 (7)
H30.16620.26640.59410.074*
C20.09330 (16)0.1156 (3)0.69105 (19)0.0505 (6)
C110.33163 (17)0.5062 (3)0.8811 (2)0.0608 (7)
H110.30730.50200.80540.073*
C70.00448 (17)0.0575 (3)0.7016 (2)0.0592 (7)
H7−0.0057−0.01560.76140.071*
C40.03367 (17)0.2726 (3)0.5241 (2)0.0624 (7)
H40.04400.34390.46350.075*
C100.33245 (15)0.3570 (3)0.9471 (2)0.0539 (6)
C6−0.06975 (17)0.1060 (3)0.6249 (2)0.0618 (7)
H6−0.12940.06570.63310.074*
C90.29580 (16)0.1870 (3)0.8972 (2)0.0659 (7)
H9A0.34100.13580.85240.079*
H9B0.28550.10620.95720.079*
C120.36687 (17)0.6610 (3)0.9274 (2)0.0625 (7)
H120.36620.76080.88280.075*
C140.40499 (17)0.5201 (3)1.1048 (2)0.0619 (7)
H140.43020.52411.18010.074*
C150.36940 (16)0.3653 (3)1.0584 (2)0.0625 (7)
H150.37050.26571.10310.075*
C8−0.13138 (19)0.2686 (3)0.4553 (2)0.0640 (7)
N20.46806 (17)0.9545 (3)1.1316 (2)0.0850 (8)
N1−0.19108 (17)0.3162 (3)0.3912 (2)0.0883 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0528 (10)0.0591 (10)0.0733 (11)0.0012 (8)−0.0121 (8)−0.0152 (8)
C130.0438 (13)0.0670 (16)0.0511 (15)−0.0015 (11)0.0004 (11)−0.0064 (12)
C50.0529 (15)0.0533 (14)0.0521 (15)0.0004 (11)0.0024 (12)−0.0107 (11)
C10.0591 (16)0.0546 (15)0.0677 (17)−0.0037 (12)0.0000 (13)−0.0063 (12)
C160.0568 (16)0.0752 (19)0.0604 (17)−0.0035 (13)−0.0009 (13)−0.0087 (14)
C30.0477 (15)0.0689 (17)0.0690 (17)−0.0086 (12)0.0107 (13)0.0035 (13)
C20.0524 (14)0.0463 (13)0.0527 (15)−0.0039 (11)0.0050 (11)−0.0096 (11)
C110.0572 (16)0.0742 (18)0.0479 (15)−0.0013 (12)−0.0078 (12)−0.0039 (13)
C70.0594 (16)0.0601 (16)0.0586 (16)−0.0125 (12)0.0082 (13)−0.0004 (12)
C40.0607 (17)0.0676 (17)0.0600 (16)−0.0025 (13)0.0117 (13)0.0057 (12)
C100.0405 (13)0.0632 (16)0.0567 (15)0.0052 (11)−0.0002 (11)−0.0076 (12)
C60.0525 (15)0.0656 (17)0.0678 (17)−0.0138 (12)0.0086 (13)−0.0060 (13)
C90.0538 (15)0.0664 (17)0.0743 (18)0.0051 (12)−0.0065 (13)−0.0083 (13)
C120.0646 (16)0.0652 (17)0.0558 (16)−0.0057 (13)−0.0020 (13)0.0029 (12)
C140.0548 (16)0.0772 (19)0.0508 (15)0.0023 (13)−0.0072 (12)−0.0038 (13)
C150.0580 (15)0.0650 (17)0.0619 (17)0.0042 (12)−0.0044 (13)0.0063 (13)
C80.0621 (17)0.0638 (17)0.0654 (18)−0.0015 (13)0.0041 (14)−0.0083 (13)
N20.0928 (19)0.0813 (18)0.0772 (17)−0.0108 (14)−0.0071 (14)−0.0135 (14)
N10.0732 (16)0.0958 (18)0.0919 (19)0.0035 (14)−0.0094 (14)0.0044 (15)

Geometric parameters (Å, °)

O1—C91.414 (3)C11—C121.382 (3)
O1—C11.414 (2)C11—C101.387 (3)
C13—C141.374 (3)C11—H110.9300
C13—C121.375 (3)C7—C61.380 (3)
C13—C161.445 (3)C7—H70.9300
C5—C61.379 (3)C4—H40.9300
C5—C41.380 (3)C10—C151.373 (3)
C5—C81.441 (3)C10—C91.504 (3)
C1—C21.497 (3)C6—H60.9300
C1—H1A0.9700C9—H9A0.9700
C1—H1B0.9700C9—H9B0.9700
C16—N21.142 (3)C12—H120.9300
C3—C41.374 (3)C14—C151.384 (3)
C3—C21.384 (3)C14—H140.9300
C3—H30.9300C15—H150.9300
C2—C71.377 (3)C8—N11.145 (3)
C9—O1—C1112.70 (17)C3—C4—C5119.9 (2)
C14—C13—C12120.0 (2)C3—C4—H4120.1
C14—C13—C16119.0 (2)C5—C4—H4120.1
C12—C13—C16121.0 (2)C15—C10—C11119.1 (2)
C6—C5—C4119.8 (2)C15—C10—C9120.2 (2)
C6—C5—C8121.0 (2)C11—C10—C9120.7 (2)
C4—C5—C8119.2 (2)C5—C6—C7119.7 (2)
O1—C1—C2108.22 (18)C5—C6—H6120.1
O1—C1—H1A110.1C7—C6—H6120.1
C2—C1—H1A110.1O1—C9—C10109.29 (19)
O1—C1—H1B110.1O1—C9—H9A109.8
C2—C1—H1B110.1C10—C9—H9A109.8
H1A—C1—H1B108.4O1—C9—H9B109.8
N2—C16—C13178.5 (3)C10—C9—H9B109.8
C4—C3—C2121.0 (2)H9A—C9—H9B108.3
C4—C3—H3119.5C13—C12—C11120.1 (2)
C2—C3—H3119.5C13—C12—H12119.9
C7—C2—C3118.5 (2)C11—C12—H12119.9
C7—C2—C1121.8 (2)C13—C14—C15119.8 (2)
C3—C2—C1119.7 (2)C13—C14—H14120.1
C12—C11—C10120.2 (2)C15—C14—H14120.1
C12—C11—H11119.9C10—C15—C14120.8 (2)
C10—C11—H11119.9C10—C15—H15119.6
C2—C7—C6121.1 (2)C14—C15—H15119.6
C2—C7—H7119.4N1—C8—C5178.1 (3)
C6—C7—H7119.4

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14···N2i0.932.603.490 (3)162

Symmetry codes: (i) −x+1, y−1/2, −z+5/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2229).

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]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography