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(Z)-2-Amino-3-[(E)-benzyl­­idene­amino]but-2-enedi­nitrile

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, Kerala, India
*Correspondence e-mail: yusuff@cusat.ac.in

(Received 17 March 2009; accepted 24 March 2009; online 28 March 2009)

The asymmetric unit of the title compound, C11H8N4, contains two independent mol­ecules. In the crystal structure, inter­molecular N—H⋯N hydrogen bonds link mol­ecules into ribbons extended in the [100] direction.

Related literature

For some properties of Schiff base ligands, see: Arun, Robinson et al. (2009[Arun, V., Robinson, P. P., Manju, S., Leeju, P., Varsha, G., Digna, V. & Yusuff, K. K. M. (2009). Dyes Pigments. In the press. doi:10.1016/j.dyepig.2009.01.010]); Arun, Sridevi et al. (2009[Arun, V., Sridevi, N., Robinson, P. P., Manju, S. & Yusuff, K. K. M. (2009). J. Mol. Catal. A Chem. In the press. doi:10.1016/j.molcata.2009.02.011]). For related structures, see: MacLachlan et al. (1996[MacLachlan, M. J., Park, M. K. & Thomas, L. K. (1996). Inorg. Chem. 35, 5492-5499.]); Mague & Eduok (2000[Mague, J. T. & Eduok, E. E. (2000). J. Chem. Crystallogr. 30, 311-320.]); Varghese et al. (2009[Varghese, D., Arun, V., Sebastian, M., Leeju, P., Varsha, G. & Yusuff, K. K. M. (2009). Acta Cryst. E65, o435.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8N4

  • Mr = 196.21

  • Monoclinic, P 21 /c

  • a = 6.9569 (19) Å

  • b = 22.796 (6) Å

  • c = 13.516 (4) Å

  • β = 100.983 (5)°

  • V = 2104.2 (10) Å3

  • Z = 8

  • Mo Kα radiation radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.42 × 0.18 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.980, Tmax = 0.984

  • 12239 measured reflections

  • 4173 independent reflections

  • 3216 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.106

  • wR(F2) = 0.214

  • S = 1.29

  • 4173 reflections

  • 272 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 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
N2—H2A⋯N3i 0.86 2.36 3.096 (4) 144
N2—H2B⋯N8ii 0.86 2.25 3.090 (5) 165
N6—H6A⋯N7iii 0.86 2.51 3.228 (5) 142
N6—H6B⋯N4iv 0.86 2.28 3.057 (4) 150
Symmetry codes: (i) x-1, y, z; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x+1, y, z; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In continuation of our study of Schiff base ligands and their metal complexes (Arun, Robinson et al., 2009; Arun, Sridevi et al., 2009; Varghese et al., 2009), we present here the title compound, (I).

The asymmetric unit of (I) contains two independent molecules (Fig. 1). All bond lengths and angles in (I) are normal and correspond to those observed in the related compounds (MacLachlan et al., 1996; Mague & Eduok 2000). In both independent molecules, the benzene ring and diaminomaleonitrile moiety are anti with respect to azomethine C=N. In the crystal structure, intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into ribbons extended in direction [100].

Related literature top

For some properties of Schiff base ligands, see: Arun, Robinson et al. (2009); Arun, Sridevi et al. (2009). For related structures, see: MacLachlan et al. (1996); Mague & Eduok (2000); Varghese et al. (2009).

Experimental top

Benzaldehyde (Merck) and 2,3-diaminomaleonitrile (Aldrich) are of reagent grade and are used without further purification. A hot solution of 2,3-diaminomaleonitrile (1 mmol) in methanol (25 ml) was added slowly over a hot solution of benzaldehyde (1 mmol) in the same solvent (25 ml) and the solution was refluxed for three hours. The resulting yellow solution was cooled in ice and the precipitated imine was filtered off and washed with cold methanol and dried under vacuum. Yellow crystals of (1) suitable for X-ray analysis were obtained by slow evaporation of the Schiff base in absolute ethanol (yield 85%; m.p. 463 K).

Refinement top

H atoms were positioned geometrically (C—H = 0.93 Å, N—H = 0.86 Å) and refined in riding mode, with Uiso (H) = 1.2Ueq(C, N).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Two independent molecules of (I) with the atomic labelling scheme and 50% probability displacement ellipsoids.
(Z)-2-Amino-3-[(E)-benzylideneamino]but-2-enedinitrile top
Crystal data top
C11H8N4F(000) = 816
Mr = 196.21Dx = 1.239 Mg m3
Monoclinic, P21/cMo Kα radiation radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4803 reflections
a = 6.9569 (19) Åθ = 2.4–26.1°
b = 22.796 (6) ŵ = 0.08 mm1
c = 13.516 (4) ÅT = 298 K
β = 100.983 (5)°Rod, yellow
V = 2104.2 (10) Å30.42 × 0.18 × 0.18 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4173 independent reflections
Radiation source: fine-focus sealed tube3216 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 26.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 88
Tmin = 0.980, Tmax = 0.984k = 2823
12239 measured reflectionsl = 1615
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)] = 0.106H-atom parameters constrained
wR(F2) = 0.214 w = 1/[σ2(Fo2) + (0.0476P)2 + 1.6604P]
where P = (Fo2 + 2Fc2)/3
S = 1.29(Δ/σ)max < 0.001
4173 reflectionsΔρmax = 0.22 e Å3
272 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (6)
Crystal data top
C11H8N4V = 2104.2 (10) Å3
Mr = 196.21Z = 8
Monoclinic, P21/cMo Kα radiation
a = 6.9569 (19) ŵ = 0.08 mm1
b = 22.796 (6) ÅT = 298 K
c = 13.516 (4) Å0.42 × 0.18 × 0.18 mm
β = 100.983 (5)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4173 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
3216 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.984Rint = 0.036
12239 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1060 restraints
wR(F2) = 0.214H-atom parameters constrained
S = 1.29Δρmax = 0.22 e Å3
4173 reflectionsΔρmin = 0.21 e Å3
272 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
C10.3264 (5)0.39467 (14)0.3626 (2)0.0398 (8)
C20.3971 (6)0.34110 (16)0.3379 (3)0.0590 (11)
H20.51960.33870.32020.071*
C30.2851 (8)0.29092 (19)0.3397 (4)0.0772 (14)
H30.33240.25480.32290.093*
C40.1054 (8)0.2944 (2)0.3661 (4)0.0792 (15)
H40.03130.26060.36770.095*
C50.0339 (6)0.3473 (2)0.3902 (3)0.0673 (12)
H50.08870.34940.40780.081*
C60.1427 (5)0.39773 (17)0.3883 (3)0.0501 (9)
H60.09330.43370.40430.060*
C70.4454 (5)0.44731 (14)0.3591 (3)0.0388 (8)
H70.56840.44360.34220.047*
C80.5013 (4)0.54703 (14)0.3760 (2)0.0366 (8)
C90.4227 (5)0.60037 (14)0.3899 (3)0.0397 (8)
C100.6996 (5)0.54341 (15)0.3605 (3)0.0469 (9)
C110.5356 (5)0.65316 (15)0.3859 (3)0.0459 (9)
N10.3855 (4)0.49769 (11)0.3784 (2)0.0367 (7)
N20.2412 (4)0.60811 (13)0.4084 (2)0.0558 (9)
H2A0.16730.57830.41220.067*
H2B0.19910.64290.41650.067*
N30.8559 (5)0.53781 (16)0.3485 (3)0.0764 (12)
N40.6208 (5)0.69534 (14)0.3808 (3)0.0693 (11)
C120.2008 (5)0.53605 (15)0.1295 (3)0.0452 (9)
C130.3849 (5)0.53053 (17)0.1052 (3)0.0550 (10)
H130.43120.49340.09330.066*
C140.4994 (7)0.5783 (2)0.0985 (4)0.0736 (13)
H140.62240.57390.08190.088*
C150.4310 (8)0.6331 (2)0.1165 (4)0.0823 (16)
H150.50780.66590.11090.099*
C160.2515 (9)0.64021 (18)0.1425 (4)0.0821 (16)
H160.20900.67750.15620.098*
C170.1334 (7)0.59197 (17)0.1484 (3)0.0639 (12)
H170.01040.59670.16480.077*
C180.0775 (5)0.48496 (15)0.1349 (3)0.0450 (9)
H180.04320.48990.15380.054*
C190.0133 (4)0.38528 (14)0.1179 (3)0.0379 (8)
C200.0863 (5)0.33203 (15)0.0987 (3)0.0416 (8)
C210.1801 (5)0.38947 (15)0.1396 (3)0.0450 (9)
C220.0336 (6)0.28020 (17)0.0983 (3)0.0540 (10)
N50.1316 (4)0.43361 (12)0.1143 (2)0.0396 (7)
N60.2648 (4)0.32364 (12)0.0767 (2)0.0555 (9)
H6A0.34100.35310.07410.067*
H6B0.30280.28880.06520.067*
N70.3334 (4)0.39419 (15)0.1568 (3)0.0660 (10)
N80.1258 (5)0.23914 (15)0.0977 (3)0.0809 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0501 (19)0.0328 (18)0.0338 (19)0.0032 (15)0.0015 (15)0.0035 (15)
C20.070 (3)0.036 (2)0.069 (3)0.0021 (19)0.007 (2)0.002 (2)
C30.112 (4)0.035 (2)0.079 (3)0.002 (3)0.006 (3)0.005 (2)
C40.110 (4)0.053 (3)0.070 (3)0.038 (3)0.006 (3)0.010 (2)
C50.067 (3)0.069 (3)0.064 (3)0.026 (2)0.009 (2)0.003 (2)
C60.056 (2)0.042 (2)0.052 (2)0.0072 (17)0.0069 (18)0.0007 (18)
C70.0369 (17)0.0353 (19)0.045 (2)0.0016 (14)0.0104 (15)0.0001 (15)
C80.0334 (16)0.0365 (19)0.0387 (19)0.0038 (14)0.0042 (14)0.0004 (15)
C90.0413 (18)0.0328 (18)0.044 (2)0.0093 (15)0.0064 (15)0.0002 (16)
C100.044 (2)0.039 (2)0.059 (2)0.0075 (16)0.0116 (17)0.0016 (17)
C110.051 (2)0.034 (2)0.050 (2)0.0021 (17)0.0028 (17)0.0064 (17)
N10.0324 (13)0.0315 (15)0.0451 (17)0.0031 (12)0.0045 (12)0.0013 (13)
N20.0506 (17)0.0364 (17)0.085 (3)0.0009 (14)0.0238 (17)0.0085 (16)
N30.0413 (18)0.066 (2)0.127 (4)0.0080 (17)0.030 (2)0.011 (2)
N40.078 (2)0.038 (2)0.089 (3)0.0181 (18)0.010 (2)0.0034 (18)
C120.057 (2)0.0302 (19)0.042 (2)0.0028 (16)0.0046 (17)0.0012 (16)
C130.060 (2)0.048 (2)0.057 (3)0.0086 (19)0.010 (2)0.0004 (19)
C140.085 (3)0.058 (3)0.077 (3)0.026 (2)0.013 (3)0.002 (2)
C150.109 (4)0.060 (3)0.070 (3)0.038 (3)0.005 (3)0.007 (3)
C160.125 (4)0.022 (2)0.084 (4)0.002 (3)0.018 (3)0.002 (2)
C170.078 (3)0.040 (2)0.067 (3)0.009 (2)0.006 (2)0.006 (2)
C180.0454 (19)0.044 (2)0.045 (2)0.0033 (16)0.0091 (16)0.0035 (17)
C190.0361 (16)0.0337 (19)0.043 (2)0.0032 (14)0.0058 (15)0.0029 (15)
C200.0466 (19)0.0349 (19)0.043 (2)0.0065 (15)0.0083 (16)0.0014 (16)
C210.0450 (19)0.038 (2)0.051 (2)0.0029 (16)0.0064 (17)0.0022 (17)
C220.054 (2)0.041 (2)0.070 (3)0.0045 (18)0.017 (2)0.006 (2)
N50.0410 (15)0.0309 (15)0.0456 (17)0.0022 (12)0.0050 (13)0.0021 (13)
N60.0520 (18)0.0287 (16)0.093 (3)0.0009 (14)0.0315 (18)0.0022 (16)
N70.0443 (18)0.070 (2)0.088 (3)0.0002 (17)0.0241 (18)0.002 (2)
N80.072 (2)0.046 (2)0.127 (4)0.0218 (19)0.026 (2)0.005 (2)
Geometric parameters (Å, º) top
C1—C21.381 (5)C12—C131.387 (5)
C1—C61.389 (5)C12—C171.398 (5)
C1—C71.464 (4)C12—C181.457 (5)
C2—C31.387 (6)C13—C141.362 (5)
C2—H20.9300C13—H130.9300
C3—C41.365 (7)C14—C151.375 (6)
C3—H30.9300C14—H140.9300
C4—C51.369 (6)C15—C161.370 (7)
C4—H40.9300C15—H150.9300
C5—C61.378 (5)C16—C171.384 (6)
C5—H50.9300C16—H160.9300
C6—H60.9300C17—H170.9300
C7—N11.266 (4)C18—N51.276 (4)
C7—H70.9300C18—H180.9300
C8—C91.360 (4)C19—C201.360 (4)
C8—N11.387 (4)C19—N51.382 (4)
C8—C101.437 (4)C19—C211.434 (4)
C9—N21.345 (4)C20—N61.344 (4)
C9—C111.443 (4)C20—C221.446 (5)
C10—N31.136 (4)C21—N71.139 (4)
C11—N41.138 (4)C22—N81.134 (4)
N2—H2A0.8600N6—H6A0.8600
N2—H2B0.8600N6—H6B0.8600
C2—C1—C6119.5 (3)C13—C12—C17118.9 (4)
C2—C1—C7119.2 (3)C13—C12—C18121.2 (3)
C6—C1—C7121.3 (3)C17—C12—C18119.9 (4)
C1—C2—C3119.9 (4)C14—C13—C12121.4 (4)
C1—C2—H2120.1C14—C13—H13119.3
C3—C2—H2120.1C12—C13—H13119.3
C4—C3—C2120.1 (4)C13—C14—C15119.2 (5)
C4—C3—H3119.9C13—C14—H14120.4
C2—C3—H3119.9C15—C14—H14120.4
C3—C4—C5120.3 (4)C16—C15—C14121.1 (4)
C3—C4—H4119.8C16—C15—H15119.5
C5—C4—H4119.8C14—C15—H15119.5
C4—C5—C6120.3 (4)C15—C16—C17120.1 (4)
C4—C5—H5119.8C15—C16—H16120.0
C6—C5—H5119.8C17—C16—H16120.0
C5—C6—C1119.8 (4)C16—C17—C12119.4 (4)
C5—C6—H6120.1C16—C17—H17120.3
C1—C6—H6120.1C12—C17—H17120.3
N1—C7—C1121.8 (3)N5—C18—C12121.4 (3)
N1—C7—H7119.1N5—C18—H18119.3
C1—C7—H7119.1C12—C18—H18119.3
C9—C8—N1118.1 (3)C20—C19—N5117.3 (3)
C9—C8—C10119.6 (3)C20—C19—C21119.9 (3)
N1—C8—C10122.3 (3)N5—C19—C21122.9 (3)
N2—C9—C8124.0 (3)N6—C20—C19124.3 (3)
N2—C9—C11115.7 (3)N6—C20—C22116.1 (3)
C8—C9—C11120.3 (3)C19—C20—C22119.6 (3)
N3—C10—C8176.8 (4)N7—C21—C19178.4 (4)
N4—C11—C9178.2 (4)N8—C22—C20179.1 (4)
C7—N1—C8121.0 (3)C18—N5—C19121.4 (3)
C9—N2—H2A120.0C20—N6—H6A120.0
C9—N2—H2B120.0C20—N6—H6B120.0
H2A—N2—H2B120.0H6A—N6—H6B120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.862.363.096 (4)144
N2—H2B···N8ii0.862.253.090 (5)165
N6—H6A···N7iii0.862.513.228 (5)142
N6—H6B···N4iv0.862.283.057 (4)150
Symmetry codes: (i) x1, y, z; (ii) x, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H8N4
Mr196.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)6.9569 (19), 22.796 (6), 13.516 (4)
β (°) 100.983 (5)
V3)2104.2 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.42 × 0.18 × 0.18
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.980, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
12239, 4173, 3216
Rint0.036
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.106, 0.214, 1.29
No. of reflections4173
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.21

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.862.363.096 (4)143.6
N2—H2B···N8ii0.862.253.090 (5)164.7
N6—H6A···N7iii0.862.513.228 (5)141.7
N6—H6B···N4iv0.862.283.057 (4)149.9
Symmetry codes: (i) x1, y, z; (ii) x, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+1, y1/2, z+1/2.
 

Acknowledgements

The X-ray data were collected on the diffractometer facilities at the University of Hyderabad provided by the Department of Science and Technology. MS thanks KSCSTE, Trivandrum, Kerala, for financial assistance. DV gratefully acknowledges financial support from the Council of Scientific and Industrial Research (CSIR), India.

References

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