organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4-(4-Cyano­benzoyl­meth­yl)benzo­nitrile

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: zhaohong@seu.edu.cn

(Received 1 May 2008; accepted 19 May 2008; online 24 May 2008)

In the title compound, C16H10N2O, the dihedral angle formed by the benzene rings is 84.99 (7)°. The crystal structure is stabilized by inter­molecular C—H⋯N and C—H⋯O hydrogen-bond inter­actions, forming chains running parallel to the b axis.

Related literature

For related literature, see: Arıcı et al. (2004[Arıcı, C., Ülkü, D., Kırılmış, C., Koca, M. & Ahmedzade, M. (2004). Acta Cryst. E60, o1211-o1212.]); Radl et al. (2000[Radl, S., Hezky, P., Konvicka, P. & Krejgi, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Zhao (2008[Zhao, Y.-Y. (2008). Acta Cryst. E64, o761.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10N2O

  • Mr = 246.26

  • Triclinic, [P \overline 1]

  • a = 7.5217 (15) Å

  • b = 7.9759 (16) Å

  • c = 10.881 (2) Å

  • α = 96.78 (3)°

  • β = 93.34 (3)°

  • γ = 102.10 (3)°

  • V = 631.5 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 (2) K

  • 0.20 × 0.20 × 0.16 mm

Data collection
  • Rigaku Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.964, Tmax = 0.988

  • 6576 measured reflections

  • 2898 independent reflections

  • 1943 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.157

  • S = 1.04

  • 2898 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯N1i 0.93 2.62 3.486 (3) 154
C12—H12⋯O1ii 0.93 2.42 3.268 (2) 152
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Benzonitriles and their derivatives are important starting materials in the synthesis of some heterocyclic molecules (Radl et al., 2000; Arıcı et al., 2004). As part of our ongoing study on benzonitrile derivatives (Zhao, 2008), the crystal structure of one such derivatives is reported here.

The molecular structure of the title compound (Fig. 1) shows normal bond lengths and angles. The CN triple bond and C=O double bond lengths are 1.142 (2) and and 1.193 (2) Å, respectively. The benzene ring are oriented nearly perpendicular to each other, the dihedral angle they form being 84.99 (7)°. In the crystal structure, centrosymmetrically-related molecules are linked into dimeric units by intermolecular C—H···N hydrogen bonds (Table 1) forming ten-membered rings of graph-set R22(10) (Berstein et al., 1995). These dimers are further connected by intermolecular C—H···O hydrogen interactions to form chains running parallel to the b axis.

Related literature top

For related literature, see: Arıcı et al. (2004); Radl et al. (2000); Bernstein et al. (1995); Zhao (2008).

Experimental top

To a solution of sodium cyanide (2 g) in water (18 ml) was added 4-formylbenzonitrile (2.62 g). The mixture was stirred for 15 min at room temperature, then a saturated sodium hydrosulfite solution (15 ml) was added dropwise. The resulting mixture was stirred at 293K until a yellow solid was obtained. The solid was filtered and recrystallized from a mixture of methanol (18 ml) and DMF (6 ml), to give crystals of the title compound suitable for X-ray diffraction analysis on slow evaporation of the solvents.

Refinement top

All hydrogen atoms were placed at calculated positions and refined using the riding model approximation, with C—H = 0.93-0.97 Å and with Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids were drawn at the 30% probability level
4-(4-Cyanobenzoylmethyl)benzonitrile top
Crystal data top
C16H10N2OZ = 2
Mr = 246.26F(000) = 256
Triclinic, P1Dx = 1.295 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5217 (15) ÅCell parameters from 2232 reflections
b = 7.9759 (16) Åθ = 3.0–27.4°
c = 10.881 (2) ŵ = 0.08 mm1
α = 96.78 (3)°T = 293 K
β = 93.34 (3)°Block, yellow
γ = 102.10 (3)°0.20 × 0.20 × 0.16 mm
V = 631.5 (2) Å3
Data collection top
Rigaku Mercury2
diffractometer
2898 independent reflections
Radiation source: fine-focus sealed tube1943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scansh = 99
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1010
Tmin = 0.964, Tmax = 0.988l = 1414
6576 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.157 w = 1/[σ2(Fo2) + (0.0717P)2 + 0.1009P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
2898 reflectionsΔρmax = 0.25 e Å3
173 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.168 (18)
Crystal data top
C16H10N2Oγ = 102.10 (3)°
Mr = 246.26V = 631.5 (2) Å3
Triclinic, P1Z = 2
a = 7.5217 (15) ÅMo Kα radiation
b = 7.9759 (16) ŵ = 0.08 mm1
c = 10.881 (2) ÅT = 293 K
α = 96.78 (3)°0.20 × 0.20 × 0.16 mm
β = 93.34 (3)°
Data collection top
Rigaku Mercury2
diffractometer
2898 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
1943 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.988Rint = 0.028
6576 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.04Δρmax = 0.25 e Å3
2898 reflectionsΔρmin = 0.21 e Å3
173 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.1774 (2)0.4661 (2)0.18751 (15)0.0468 (4)
C20.0347 (3)0.5506 (2)0.18255 (17)0.0546 (5)
H20.07150.50810.21890.066*
C30.0475 (3)0.6970 (2)0.12455 (17)0.0532 (5)
H30.04930.75280.12180.064*
C40.2055 (2)0.7599 (2)0.07065 (15)0.0468 (4)
C50.3487 (3)0.6762 (2)0.07410 (17)0.0550 (5)
H50.45450.71810.03710.066*
C60.3339 (3)0.5301 (2)0.13273 (17)0.0550 (5)
H60.43060.47420.13530.066*
C70.2217 (3)0.9131 (2)0.00999 (17)0.0558 (5)
C80.2389 (2)0.2017 (2)0.46012 (15)0.0457 (4)
C90.2979 (3)0.2430 (2)0.58529 (16)0.0580 (5)
H90.31780.35710.62260.070*
C100.3274 (3)0.1162 (2)0.65476 (17)0.0599 (5)
H100.36680.14470.73870.072*
C110.2980 (2)0.0536 (2)0.59929 (16)0.0476 (4)
C120.2369 (2)0.0974 (2)0.47534 (17)0.0521 (5)
H120.21580.21180.43840.062*
C130.2074 (3)0.0309 (2)0.40669 (16)0.0508 (5)
H130.16560.00180.32320.061*
C140.3367 (3)0.1839 (2)0.67244 (18)0.0560 (5)
C150.2138 (3)0.3455 (2)0.38867 (17)0.0589 (5)
N10.2355 (3)1.0349 (2)0.03745 (18)0.0757 (5)
N20.3690 (3)0.2834 (2)0.73238 (17)0.0742 (6)
O10.2335 (4)0.48933 (19)0.44054 (14)0.1312 (10)
C160.1648 (3)0.3057 (2)0.25106 (16)0.0529 (5)
H16A0.04130.23650.23580.063*
H16B0.24580.23740.21470.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0585 (11)0.0387 (8)0.0433 (9)0.0106 (8)0.0022 (8)0.0092 (7)
C20.0563 (11)0.0512 (10)0.0595 (11)0.0119 (9)0.0080 (9)0.0189 (9)
C30.0581 (11)0.0491 (10)0.0585 (11)0.0204 (8)0.0042 (9)0.0166 (8)
C40.0600 (11)0.0400 (8)0.0405 (8)0.0105 (8)0.0016 (8)0.0090 (7)
C50.0575 (11)0.0531 (10)0.0572 (11)0.0126 (9)0.0064 (9)0.0171 (9)
C60.0573 (11)0.0531 (10)0.0592 (11)0.0196 (9)0.0014 (9)0.0142 (9)
C70.0694 (13)0.0504 (10)0.0516 (10)0.0168 (9)0.0060 (9)0.0153 (8)
C80.0579 (10)0.0367 (8)0.0456 (9)0.0140 (7)0.0060 (8)0.0104 (7)
C90.0864 (14)0.0370 (9)0.0500 (10)0.0134 (9)0.0019 (10)0.0055 (8)
C100.0798 (14)0.0507 (10)0.0478 (10)0.0099 (10)0.0036 (9)0.0133 (8)
C110.0474 (9)0.0431 (9)0.0569 (10)0.0109 (7)0.0092 (8)0.0212 (8)
C120.0656 (12)0.0330 (8)0.0596 (11)0.0121 (8)0.0076 (9)0.0106 (8)
C130.0668 (11)0.0378 (9)0.0486 (10)0.0132 (8)0.0022 (8)0.0073 (7)
C140.0566 (11)0.0512 (10)0.0661 (12)0.0144 (9)0.0103 (9)0.0243 (9)
C150.0930 (15)0.0367 (9)0.0514 (10)0.0225 (9)0.0028 (10)0.0108 (8)
N10.0880 (13)0.0672 (11)0.0853 (13)0.0269 (10)0.0212 (10)0.0399 (10)
N20.0837 (13)0.0672 (11)0.0843 (13)0.0263 (10)0.0116 (10)0.0410 (10)
O10.296 (3)0.0429 (8)0.0603 (10)0.0630 (13)0.0189 (13)0.0018 (7)
C160.0680 (12)0.0387 (9)0.0527 (10)0.0126 (8)0.0010 (9)0.0108 (8)
Geometric parameters (Å, º) top
C1—C61.380 (3)C8—C151.496 (2)
C1—C21.383 (2)C9—C101.377 (2)
C1—C161.513 (2)C9—H90.9300
C2—C31.381 (2)C10—C111.384 (3)
C2—H20.9300C10—H100.9300
C3—C41.381 (3)C11—C121.379 (2)
C3—H30.9300C11—C141.446 (2)
C4—C51.382 (3)C12—C131.382 (2)
C4—C71.442 (2)C12—H120.9300
C5—C61.381 (2)C13—H130.9300
C5—H50.9300C14—N21.140 (2)
C6—H60.9300C15—O11.193 (2)
C7—N11.142 (2)C15—C161.501 (3)
C8—C131.383 (2)C16—H16A0.9700
C8—C91.387 (2)C16—H16B0.9700
C6—C1—C2118.89 (15)C8—C9—H9119.7
C6—C1—C16119.65 (16)C9—C10—C11119.80 (17)
C2—C1—C16121.46 (16)C9—C10—H10120.1
C3—C2—C1121.07 (17)C11—C10—H10120.1
C3—C2—H2119.5C12—C11—C10120.45 (15)
C1—C2—H2119.5C12—C11—C14120.50 (16)
C2—C3—C4119.32 (17)C10—C11—C14119.03 (17)
C2—C3—H3120.3C11—C12—C13119.21 (16)
C4—C3—H3120.3C11—C12—H12120.4
C3—C4—C5120.28 (15)C13—C12—H12120.4
C3—C4—C7120.13 (16)C12—C13—C8121.10 (17)
C5—C4—C7119.59 (16)C12—C13—H13119.5
C6—C5—C4119.70 (17)C8—C13—H13119.5
C6—C5—H5120.2N2—C14—C11178.3 (2)
C4—C5—H5120.2O1—C15—C8120.30 (17)
C1—C6—C5120.74 (17)O1—C15—C16120.78 (16)
C1—C6—H6119.6C8—C15—C16118.92 (15)
C5—C6—H6119.6C15—C16—C1113.15 (14)
N1—C7—C4179.5 (2)C15—C16—H16A108.9
C13—C8—C9118.91 (15)C1—C16—H16A108.9
C13—C8—C15122.97 (16)C15—C16—H16B108.9
C9—C8—C15118.12 (15)C1—C16—H16B108.9
C10—C9—C8120.52 (16)H16A—C16—H16B107.8
C10—C9—H9119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N1i0.932.623.486 (3)154
C12—H12···O1ii0.932.423.268 (2)152
Symmetry codes: (i) x, y+2, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC16H10N2O
Mr246.26
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.5217 (15), 7.9759 (16), 10.881 (2)
α, β, γ (°)96.78 (3), 93.34 (3), 102.10 (3)
V3)631.5 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.20 × 0.16
Data collection
DiffractometerRigaku Mercury2
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.964, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
6576, 2898, 1943
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.157, 1.04
No. of reflections2898
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.21

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N1i0.932.623.486 (3)154
C12—H12···O1ii0.932.423.268 (2)152
Symmetry codes: (i) x, y+2, z; (ii) x, y1, z.
 

Acknowledgements

This work was supported by a Start-up Grant from SEU to Professor Ren-Gen Xiong.

References

First citationArıcı, C., Ülkü, D., Kırılmış, C., Koca, M. & Ahmedzade, M. (2004). Acta Cryst. E60, o1211–o1212.  Web of Science CSD CrossRef IUCr Journals
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationRadl, S., Hezky, P., Konvicka, P. & Krejgi, J. (2000). Collect. Czech. Chem. Commun. 65, 1093–1108.  Web of Science CrossRef CAS
First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZhao, Y.-Y. (2008). Acta Cryst. E64, o761.  Web of Science CSD CrossRef IUCr Journals

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ISSN: 2056-9890
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