PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2491.
Published online 2009 September 19. doi:  10.1107/S1600536809037179
PMCID: PMC2970396

1-(But-2-enyl­idene)-2-(2-nitro­phen­yl)hydrazine

Abstract

The mol­ecule of the title Schiff base compound, C10H11N3O2, adopts an E geometry with respect to the C=N double bond. The mol­ecule is roughly planar, with the largest deviation from the mean plane being 0.111 (2) Å, The enyl­idene-hydrazine group is, however, slightly twisted with respect to the phenyl ring, making a dihedral angle of 6.5 (3)°. An intra­molecular N—H(...)O hydrogen bond may be responsible for the planar conformation. An inter­molecular N—H(...)O hydrogen bond links two mol­ecules around an inversion center, building a pseudo dimer.

Related literature

For the role played by Schiff base compounds in the development of various proteins and enzymes, see: Kahwa et al. (1986 [triangle]); Santos et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2491-scheme1.jpg

Experimental

Crystal data

  • C10H11N3O2
  • M r = 205.22
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2491-efi1.jpg
  • a = 4.2390 (6) Å
  • b = 11.456 (2) Å
  • c = 11.9840 (17) Å
  • α = 113.271 (15)°
  • β = 96.534 (12)°
  • γ = 95.595 (13)°
  • V = 524.64 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.25 × 0.19 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.979, T max = 0.982
  • 3321 measured reflections
  • 1758 independent reflections
  • 587 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.080
  • S = 0.68
  • 1758 reflections
  • 137 parameters
  • H-atom parameters constrained
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]), ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037179/dn2487sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037179/dn2487Isup2.hkl

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

Acknowledgments

The authors would like to express their deep appreciation to the PhD startup fund of the Fund for Natural Scientific Research of Zhengzhou University of Light Industry (grant No. 2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry (grant No. 000455).

supplementary crystallographic information

Comment

The chemistry of Schiff base has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our in the study of the coordination chemistry of Schiff bases, we synthesized the title compound and determined its crystal structure.

The molecule is roughly planar with the largest deviation from the mean plane being -0.111 (2) Å at O1 (Fig. 1). The enylidene-hydrazine group is however slightly twisted with respect to the phenyl ring making a dihedral angle of 6.5 (3)° .

Intramolecular N—H···O bond may be responsible for the planar conformation whereas intermolecular N—H···O links two molecules around the inversion center buiding a pseudo dimer (Table 1, Fig. 2).

Experimental

2-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (15 ml), The mixture was stirred for several minitutes at 351 K, but-2-enal (1 mmol, 0.070 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol, red single crystals of (I) was obtained after 3 d.

Refinement

H atoms were placed in calculated position and treated as riding with C—H = 0.93 Å(aromatic), 0.96 Å(methyl) and N—H = 0.86Å with Uiso(H) = 1.2Ueq(C,N) or Uiso(H) = 1.5Ueq(methyl).

Figures

Fig. 1.
Molecular view of (I) with the atomlabeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Partial packing of (I), showing the intra and intermolecular hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) -x+2, -y, -z]

Crystal data

C10H11N3O2Z = 2
Mr = 205.22F(000) = 216
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.2390 (6) ÅCell parameters from 1958 reflections
b = 11.456 (2) Åθ = 3.2–26.0°
c = 11.9840 (17) ŵ = 0.09 mm1
α = 113.271 (15)°T = 296 K
β = 96.534 (12)°Block, red
γ = 95.595 (13)°0.25 × 0.19 × 0.18 mm
V = 524.64 (16) Å3

Data collection

Bruker SMART CCD area-detector diffractometer1758 independent reflections
Radiation source: fine-focus sealed tube587 reflections with I > 2σ(I)
graphiteRint = 0.039
ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −5→4
Tmin = 0.979, Tmax = 0.982k = −13→12
3321 measured reflectionsl = 0→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 0.68w = 1/[σ2(Fo2) + (0.0315P)2] where P = (Fo2 + 2Fc2)/3
1758 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = −0.11 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C11.2639 (7)0.1906 (3)−0.4898 (3)0.0923 (12)
H1A1.18680.2699−0.47860.138*
H1B1.15350.1237−0.56610.138*
H1C1.49050.2007−0.49160.138*
C21.2028 (7)0.1556 (3)−0.3856 (3)0.0637 (10)
H21.27650.0820−0.38510.076*
C31.0549 (7)0.2191 (3)−0.2947 (3)0.0601 (10)
H30.97570.2916−0.29580.072*
C41.0060 (7)0.1857 (3)−0.1944 (3)0.0549 (9)
H41.07910.1129−0.19130.066*
C50.6836 (7)0.2802 (3)0.0774 (2)0.0451 (9)
C60.6046 (6)0.4007 (3)0.0883 (3)0.0584 (9)
H60.64890.43080.02930.070*
C70.4654 (7)0.4732 (3)0.1834 (3)0.0681 (10)
H70.41530.55200.18790.082*
C80.3955 (8)0.4328 (4)0.2745 (3)0.0767 (11)
H80.30120.48400.33940.092*
C90.4679 (7)0.3169 (3)0.2666 (3)0.0641 (10)
H90.42280.28830.32650.077*
C100.6101 (7)0.2408 (3)0.1686 (2)0.0497 (9)
N10.8634 (6)0.2541 (2)−0.1088 (2)0.0553 (7)
N20.8205 (5)0.2108 (2)−0.01925 (19)0.0548 (8)
H2A0.88070.1395−0.02460.066*
N30.6751 (6)0.1190 (3)0.1671 (2)0.0634 (8)
O10.5896 (6)0.0865 (2)0.2464 (2)0.0933 (9)
O20.8241 (5)0.05249 (18)0.08917 (18)0.0722 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.096 (3)0.119 (3)0.074 (2)0.006 (2)0.027 (2)0.051 (2)
C20.075 (3)0.063 (2)0.062 (2)0.006 (2)0.0186 (19)0.0343 (19)
C30.069 (3)0.065 (3)0.057 (2)0.014 (2)0.011 (2)0.0350 (19)
C40.063 (2)0.052 (2)0.057 (2)0.0116 (19)0.0080 (18)0.0305 (19)
C50.048 (2)0.041 (2)0.049 (2)0.0052 (18)0.0036 (17)0.0236 (18)
C60.064 (2)0.053 (2)0.072 (2)0.014 (2)0.0155 (17)0.0372 (19)
C70.084 (3)0.048 (3)0.082 (2)0.017 (2)0.022 (2)0.032 (2)
C80.080 (3)0.071 (3)0.082 (3)0.025 (2)0.028 (2)0.026 (2)
C90.079 (3)0.063 (3)0.059 (2)0.016 (2)0.0244 (18)0.030 (2)
C100.057 (2)0.045 (2)0.056 (2)0.0113 (19)0.0112 (17)0.0282 (18)
N10.068 (2)0.056 (2)0.0565 (16)0.0143 (15)0.0179 (15)0.0347 (16)
N20.076 (2)0.052 (2)0.0548 (16)0.0199 (16)0.0241 (15)0.0353 (15)
N30.073 (2)0.073 (2)0.0618 (18)0.0175 (18)0.0187 (15)0.0431 (18)
O10.149 (2)0.084 (2)0.0911 (17)0.0467 (17)0.0603 (16)0.0652 (16)
O20.1081 (19)0.0611 (18)0.0802 (14)0.0410 (15)0.0499 (13)0.0479 (13)

Geometric parameters (Å, °)

C1—C21.495 (4)C6—C71.356 (3)
C1—H1A0.9600C6—H60.9300
C1—H1B0.9600C7—C81.392 (4)
C1—H1C0.9600C7—H70.9300
C2—C31.314 (3)C8—C91.361 (3)
C2—H20.9300C8—H80.9300
C3—C41.429 (3)C9—C101.399 (3)
C3—H30.9300C9—H90.9300
C4—N11.276 (3)C10—N31.442 (3)
C4—H40.9300N1—N21.371 (3)
C5—N21.351 (3)N2—H2A0.8600
C5—C101.392 (3)N3—O11.227 (3)
C5—C61.411 (3)N3—O21.232 (3)
C2—C1—H1A109.5C5—C6—H6119.4
C2—C1—H1B109.5C6—C7—C8121.7 (3)
H1A—C1—H1B109.5C6—C7—H7119.1
C2—C1—H1C109.5C8—C7—H7119.1
H1A—C1—H1C109.5C9—C8—C7118.7 (3)
H1B—C1—H1C109.5C9—C8—H8120.7
C3—C2—C1126.1 (3)C7—C8—H8120.7
C3—C2—H2116.9C8—C9—C10120.1 (3)
C1—C2—H2116.9C8—C9—H9119.9
C2—C3—C4125.2 (3)C10—C9—H9119.9
C2—C3—H3117.4C5—C10—C9121.9 (3)
C4—C3—H3117.4C5—C10—N3121.8 (3)
N1—C4—C3121.1 (3)C9—C10—N3116.3 (3)
N1—C4—H4119.5C4—N1—N2116.1 (2)
C3—C4—H4119.5C5—N2—N1119.9 (2)
N2—C5—C10124.5 (3)C5—N2—H2A120.0
N2—C5—C6119.1 (3)N1—N2—H2A120.0
C10—C5—C6116.4 (3)O1—N3—O2121.7 (3)
C7—C6—C5121.1 (3)O1—N3—C10118.9 (3)
C7—C6—H6119.4O2—N3—C10119.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.862.002.615 (3)127
N2—H2A···O2i0.862.533.353 (3)160

Symmetry codes: (i) −x+2, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2487).

References

  • Bruker (1998). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185.
  • Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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