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

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ISSN: 2056-9890

(E)-4-[4-(Di­methyl­amino)benzyl­­idene­amino]benzo­nitrile

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China, and bJiangsu Provincial Key Laboratory of Pulp and Paper Science and Technology, Nanjing Forestry University, Nanjing 210037, People's Republic of China
*Correspondence e-mail: jczhou@seu.edu.cn

(Received 1 November 2009; accepted 6 November 2009; online 14 November 2009)

The mol­ecule of the title compound, C16H15N3, displays a trans configuration with respect to the C=N double bond. The mol­ecule is not planar, the dihedral angle between the benzene rings being 57.83 (9)°. The crystal packing is stabilized only by van der Waals inter­actions.

Related literature

For the pharmacological activity of Schiff base compounds, see: Zhou et al. (2000[Zhou, Y.-S., Zhang, L.-J., Zeng, X.-R., Vittal, J. J. & You, X.-Z. (2000). J. Mol. Struct. 524, 241-250.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3

  • Mr = 249.31

  • Monoclinic, P 21 /c

  • a = 9.733 (6) Å

  • b = 16.159 (9) Å

  • c = 9.103 (6) Å

  • β = 110.644 (12)°

  • V = 1339.8 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.985, Tmax = 0.985

  • 13048 measured reflections

  • 2610 independent reflections

  • 2134 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.221

  • S = 1.09

  • 2610 reflections

  • 172 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); 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: SHELXL97.

Supporting information


Comment top

Schiff bases compounds are of great interest in many fields of chemistry and biochemistry, primarily due to significant pharmacological activities, e. g. anticancer (Zhou et al., 2000) and anti-HIV (Sriram et al., 2006) activities. In addition, Schiff base compounds play an important role in the development of coordination chemistry related to magnetism and catalysis. Here, we report the synthesis and crystal structure of the title compound.

The molecular structure of the the title compound is shown in Fig. 1. All bond lengths (Allen et al., 1987) and angles in the molecule are normal. The N=C bond distance is 1.288 (3) Å. The structure displays a trans configuration about the central C9=N2 double bond. The molecule is not planar, as indicated by the dihedral angle between the two benzene rings of 57.83 (9)°. The crystal packing is stabilized only by van der Waals interactions.

Related literature top

For the pharmacological activity of Schiff bases compounds, see: Zhou et al. (2000); Sriram et al. (2006). For reference structural data, see: Allen et al. (1987).

Experimental top

A solution of 4-(dimethylamino)benzaldehyde (0.596 g, 4 mmol) in ethanol (20 ml) was added to a solution of 4-aminobenzonitrile (0.472 g, 4 mmol) in methanol (20 ml), and the mixture stirred for 6 h under reflux. The resulting yellow precipitate was filtered off and crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement top

All the H atoms were located geometrically and treated as riding atoms with C—H = 0.93–0.96 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
(E)-4-[4-(Dimethylamino)benzylideneamino]benzonitrile top
Crystal data top
C16H15N3F(000) = 528
Mr = 249.31Dx = 1.236 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3347 reflections
a = 9.733 (6) Åθ = 2.2–27.5°
b = 16.159 (9) ŵ = 0.08 mm1
c = 9.103 (6) ÅT = 293 K
β = 110.644 (12)°Block, yellow
V = 1339.8 (14) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer
2610 independent reflections
Radiation source: fine-focus sealed tube2134 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = 1212
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1919
Tmin = 0.985, Tmax = 0.985l = 1111
13048 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1227P)2 + 0.7975P]
where P = (Fo2 + 2Fc2)/3
2610 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C16H15N3V = 1339.8 (14) Å3
Mr = 249.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.733 (6) ŵ = 0.08 mm1
b = 16.159 (9) ÅT = 293 K
c = 9.103 (6) Å0.20 × 0.20 × 0.20 mm
β = 110.644 (12)°
Data collection top
Rigaku SCXmini
diffractometer
2610 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
2134 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.985Rint = 0.043
13048 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.221H-atom parameters constrained
S = 1.09Δρmax = 0.53 e Å3
2610 reflectionsΔρmin = 0.36 e Å3
172 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
N20.9054 (2)0.11253 (12)0.0481 (2)0.0259 (5)
N11.3132 (2)0.12345 (13)0.7796 (2)0.0266 (5)
C41.2390 (3)0.13388 (14)0.6221 (3)0.0224 (5)
C140.7447 (3)0.19677 (16)0.3581 (3)0.0279 (6)
H14A0.72620.24720.41050.033*
C150.8167 (3)0.19445 (15)0.1968 (3)0.0254 (5)
H15A0.84790.24350.14150.030*
C91.0202 (3)0.15527 (14)0.1238 (3)0.0246 (5)
H9A1.06060.18970.06780.030*
C100.8427 (2)0.11873 (14)0.1164 (3)0.0222 (5)
C120.7285 (3)0.04706 (15)0.3620 (3)0.0278 (6)
H12A0.70080.00220.41740.033*
C110.7979 (3)0.04566 (15)0.2013 (3)0.0280 (6)
H11A0.81510.00480.14870.034*
C61.0225 (3)0.11201 (14)0.3895 (3)0.0247 (5)
H6A0.92820.09070.34390.030*
C160.6232 (3)0.12454 (17)0.6090 (3)0.0344 (6)
C130.7000 (3)0.12305 (15)0.4417 (3)0.0264 (6)
C51.0934 (3)0.10420 (15)0.5487 (3)0.0249 (5)
H5A1.04560.07920.60920.030*
C21.2299 (3)0.18366 (15)0.3669 (3)0.0260 (6)
H2B1.27490.21150.30660.031*
C31.3042 (3)0.17532 (15)0.5260 (3)0.0265 (6)
H3A1.39830.19710.57080.032*
C11.0889 (3)0.15156 (14)0.2934 (3)0.0235 (5)
N30.5616 (3)0.12575 (18)0.7415 (3)0.0523 (8)
C81.2478 (3)0.0794 (2)0.8776 (3)0.0427 (7)
H8A1.14470.07210.82110.064*
H8B1.26150.11080.97130.064*
H8C1.29390.02630.90530.064*
C71.4701 (3)0.14047 (19)0.8465 (3)0.0350 (6)
H7A1.50010.16990.77130.052*
H7B1.52310.08920.87290.052*
H7C1.49040.17350.93950.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0267 (10)0.0271 (10)0.0214 (10)0.0019 (8)0.0054 (9)0.0007 (8)
N10.0246 (11)0.0340 (12)0.0196 (10)0.0042 (8)0.0058 (8)0.0022 (8)
C40.0236 (12)0.0212 (11)0.0222 (11)0.0013 (9)0.0078 (9)0.0028 (9)
C140.0284 (13)0.0287 (13)0.0262 (13)0.0007 (10)0.0090 (10)0.0048 (10)
C150.0266 (12)0.0251 (12)0.0238 (12)0.0028 (9)0.0080 (10)0.0008 (9)
C90.0244 (12)0.0227 (12)0.0263 (12)0.0026 (9)0.0084 (10)0.0023 (9)
C100.0184 (11)0.0278 (12)0.0203 (11)0.0004 (9)0.0067 (9)0.0014 (9)
C120.0284 (13)0.0276 (13)0.0268 (13)0.0012 (10)0.0091 (10)0.0042 (10)
C110.0308 (13)0.0245 (12)0.0275 (13)0.0066 (10)0.0087 (10)0.0037 (9)
C60.0199 (11)0.0263 (12)0.0269 (12)0.0012 (9)0.0071 (10)0.0025 (9)
C160.0346 (14)0.0389 (15)0.0283 (15)0.0001 (11)0.0093 (12)0.0003 (11)
C130.0234 (12)0.0340 (14)0.0220 (12)0.0031 (10)0.0083 (10)0.0018 (9)
C50.0251 (12)0.0266 (12)0.0246 (12)0.0018 (9)0.0109 (10)0.0020 (9)
C20.0261 (12)0.0252 (12)0.0276 (12)0.0024 (10)0.0103 (10)0.0031 (9)
C30.0232 (12)0.0279 (12)0.0258 (12)0.0052 (9)0.0055 (10)0.0016 (9)
C10.0244 (12)0.0211 (11)0.0237 (12)0.0017 (9)0.0066 (10)0.0011 (9)
N30.0589 (18)0.0662 (19)0.0246 (13)0.0025 (14)0.0058 (12)0.0003 (11)
C80.0412 (16)0.063 (2)0.0232 (13)0.0160 (14)0.0105 (12)0.0014 (12)
C70.0250 (13)0.0527 (17)0.0237 (12)0.0017 (11)0.0042 (10)0.0014 (11)
Geometric parameters (Å, º) top
N2—C91.288 (3)C11—H11A0.9300
N2—C101.408 (3)C6—C51.374 (3)
N1—C41.370 (3)C6—C11.411 (3)
N1—C81.452 (3)C6—H6A0.9300
N1—C71.457 (3)C16—N31.143 (4)
C4—C31.417 (3)C16—C131.441 (3)
C4—C51.420 (3)C5—H5A0.9300
C14—C151.387 (3)C2—C31.379 (3)
C14—C131.398 (4)C2—C11.397 (3)
C14—H14A0.9300C2—H2B0.9300
C15—C101.402 (3)C3—H3A0.9300
C15—H15A0.9300C8—H8A0.9600
C9—C11.451 (3)C8—H8B0.9600
C9—H9A0.9300C8—H8C0.9600
C10—C111.394 (3)C7—H7A0.9600
C12—C111.378 (3)C7—H7B0.9600
C12—C131.403 (3)C7—H7C0.9600
C12—H12A0.9300
C9—N2—C10120.0 (2)N3—C16—C13179.6 (3)
C4—N1—C8121.3 (2)C14—C13—C12119.8 (2)
C4—N1—C7120.2 (2)C14—C13—C16120.5 (2)
C8—N1—C7117.2 (2)C12—C13—C16119.7 (2)
N1—C4—C3121.3 (2)C6—C5—C4120.8 (2)
N1—C4—C5121.4 (2)C6—C5—H5A119.6
C3—C4—C5117.3 (2)C4—C5—H5A119.6
C15—C14—C13119.8 (2)C3—C2—C1122.0 (2)
C15—C14—H14A120.1C3—C2—H2B119.0
C13—C14—H14A120.1C1—C2—H2B119.0
C14—C15—C10120.4 (2)C2—C3—C4120.7 (2)
C14—C15—H15A119.8C2—C3—H3A119.6
C10—C15—H15A119.8C4—C3—H3A119.6
N2—C9—C1122.3 (2)C2—C1—C6117.3 (2)
N2—C9—H9A118.9C2—C1—C9120.0 (2)
C1—C9—H9A118.9C6—C1—C9122.6 (2)
C11—C10—C15119.1 (2)N1—C8—H8A109.5
C11—C10—N2117.6 (2)N1—C8—H8B109.5
C15—C10—N2123.2 (2)H8A—C8—H8B109.5
C11—C12—C13119.8 (2)N1—C8—H8C109.5
C11—C12—H12A120.1H8A—C8—H8C109.5
C13—C12—H12A120.1H8B—C8—H8C109.5
C12—C11—C10121.0 (2)N1—C7—H7A109.5
C12—C11—H11A119.5N1—C7—H7B109.5
C10—C11—H11A119.5H7A—C7—H7B109.5
C5—C6—C1121.7 (2)N1—C7—H7C109.5
C5—C6—H6A119.1H7A—C7—H7C109.5
C1—C6—H6A119.1H7B—C7—H7C109.5

Experimental details

Crystal data
Chemical formulaC16H15N3
Mr249.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.733 (6), 16.159 (9), 9.103 (6)
β (°) 110.644 (12)
V3)1339.8 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.985, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
13048, 2610, 2134
Rint0.043
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.221, 1.09
No. of reflections2610
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.36

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

 

Acknowledgements

This work was supported financially by the Jiangsu Provincial Key Laboratory of Pulp and Paper Science and Technology (fund No. 200813).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129.  Web of Science CrossRef PubMed CAS Google Scholar
First citationZhou, Y.-S., Zhang, L.-J., Zeng, X.-R., Vittal, J. J. & You, X.-Z. (2000). J. Mol. Struct. 524, 241–250.  Web of Science CSD CrossRef Google Scholar

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ISSN: 2056-9890
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