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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2155.
Published online 2009 August 15. doi:  10.1107/S1600536809031420
PMCID: PMC2969877

1-(Butan-2-yl­idene)-2-(2-nitro­phen­yl)hydrazine

Abstract

Crystals of the title compound, C10H13N3O2, were obtained from a condensation reaction of butan-2-one and 1-(2-nitro­phen­yl)hydrazine. The mol­ecule exhibits a nearly coplanar structure, except for the methyl and methyl­ene H atoms, the largest deviations from the mean plane defined by all non-H atoms, except for the nitro group, being 0.120 (2) Å for one of the nitro O atoms. Intra­molecular N—H(...)O hydrogen bonding helps to establish the mol­ecular configuration.

Related literature

For applications of Schiff base compounds, see: Kahwa et al. (1986 [triangle]); Santos et al. (2001 [triangle]).

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Object name is e-65-o2155-scheme1.jpg

Experimental

Crystal data

  • C10H13N3O2
  • M r = 207.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2155-efi1.jpg
  • a = 7.3079 (11) Å
  • b = 10.2150 (17) Å
  • c = 14.763 (2) Å
  • β = 100.058 (9)°
  • V = 1085.1 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.28 × 0.21 × 0.11 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 7304 measured reflections
  • 2116 independent reflections
  • 1099 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.159
  • S = 0.93
  • 2116 reflections
  • 141 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.15 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: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031420/xu2581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031420/xu2581Isup2.hkl

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

Acknowledgments

The authors would like to express their deep appreciation to the start-up Fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (No. 2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry, China (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 molecular structure of (I) is shown in Fig. 1. The molecules is roughly planar, with the largest deviations from the mean plane defined by all non-H atoms, except the nitro group, being -0.120 (2) for atom O2.

Intramolecular N—H···O hydrogen bond is observed in compound (I), and this helps to stabilize the configuration of the molecule.

Experimental

2-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (15 ml). The mixture was stirred for several min at 351 K, then butan-2-one (1 mmol, 0.72 g) in ethanol (8 ml) 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 were obtained after 3 d.

Refinement

Imino H atom was located in a difference Fourier map and positional parameters were refined with a fixed isotropic thermal parameter of 0.08 Å2. Other H atoms were positioned geometrically and refined as riding with C—H = 0.93 (aromatic), 0.97 (methylene) and 0.96 Å (methyl), with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonding is shown in dashed line.

Crystal data

C10H13N3O2F(000) = 440
Mr = 207.23Dx = 1.268 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1572 reflections
a = 7.3079 (11) Åθ = 2.4–26.0°
b = 10.2150 (17) ŵ = 0.09 mm1
c = 14.763 (2) ÅT = 296 K
β = 100.058 (9)°Block, red
V = 1085.1 (3) Å30.28 × 0.21 × 0.11 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1099 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 26.0°, θmin = 2.4°
ω scansh = −9→8
7304 measured reflectionsk = −11→12
2116 independent reflectionsl = −13→18

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 0.93w = 1/[σ2(Fo2) + (0.0917P)2] where P = (Fo2 + 2Fc2)/3
2116 reflections(Δ/σ)max = 0.010
141 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = −0.14 e Å3

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
N10.3024 (2)1.04656 (17)0.09960 (11)0.0674 (5)
C10.2088 (2)0.89169 (19)−0.01835 (13)0.0551 (5)
N20.2496 (2)1.01728 (17)0.00803 (12)0.0678 (5)
C20.2183 (3)0.79113 (19)0.04780 (12)0.0621 (6)
H20.24950.81220.10990.075*
C60.1570 (2)0.85236 (19)−0.11104 (12)0.0587 (5)
C50.1221 (3)0.7221 (2)−0.13432 (14)0.0690 (6)
H50.08890.6985−0.19590.083*
N30.1382 (3)0.9459 (2)−0.18488 (14)0.0817 (6)
C30.1830 (3)0.66460 (19)0.02310 (14)0.0698 (6)
H30.19070.60070.06850.084*
C40.1358 (3)0.6288 (2)−0.06817 (15)0.0732 (6)
H40.11360.5415−0.08410.088*
O20.1590 (3)1.0630 (2)−0.16759 (12)0.1089 (7)
C70.3445 (3)1.1663 (2)0.11902 (16)0.0713 (6)
O10.1019 (3)0.90665 (19)−0.26427 (11)0.1204 (7)
C80.4002 (3)1.2013 (2)0.21782 (18)0.0938 (8)
H8A0.52401.23870.22660.113*
H8B0.31661.26870.23250.113*
C100.3419 (3)1.2749 (2)0.05076 (18)0.0974 (8)
H10A0.42231.25310.00800.146*
H10B0.38431.35430.08240.146*
H10C0.21751.28690.01800.146*
C90.4004 (4)1.0931 (3)0.28360 (19)0.1200 (10)
H9A0.28031.05230.27400.180*
H9B0.42861.12660.34520.180*
H9C0.49261.02980.27450.180*
H2A0.240 (3)1.0806 (15)−0.0338 (11)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0685 (11)0.0696 (12)0.0636 (12)−0.0003 (9)0.0106 (8)−0.0109 (9)
C10.0509 (11)0.0590 (12)0.0556 (12)0.0053 (9)0.0102 (8)0.0030 (10)
N20.0764 (12)0.0608 (12)0.0652 (13)0.0025 (9)0.0095 (9)0.0037 (8)
C20.0672 (13)0.0693 (14)0.0485 (11)0.0010 (10)0.0062 (9)0.0024 (10)
C60.0557 (11)0.0734 (14)0.0468 (11)0.0076 (10)0.0081 (8)0.0083 (10)
C50.0601 (13)0.0917 (17)0.0549 (12)−0.0007 (11)0.0087 (10)−0.0156 (12)
N30.0826 (13)0.1009 (16)0.0613 (13)0.0115 (11)0.0116 (9)0.0134 (12)
C30.0758 (15)0.0658 (14)0.0680 (14)−0.0028 (11)0.0126 (11)0.0065 (11)
C40.0764 (15)0.0667 (14)0.0777 (16)−0.0052 (11)0.0169 (12)−0.0077 (12)
O20.1446 (17)0.0932 (13)0.0870 (13)0.0062 (12)0.0148 (11)0.0327 (10)
C70.0523 (12)0.0700 (15)0.0934 (17)0.0034 (11)0.0173 (11)−0.0162 (13)
O10.1572 (18)0.1516 (17)0.0490 (11)0.0180 (13)0.0086 (10)0.0100 (10)
C80.0826 (16)0.0953 (18)0.106 (2)−0.0056 (13)0.0236 (14)−0.0338 (16)
C100.0861 (18)0.0704 (16)0.136 (2)0.0024 (13)0.0191 (15)0.0039 (15)
C90.135 (2)0.144 (3)0.0799 (17)−0.036 (2)0.0144 (16)−0.0224 (18)

Geometric parameters (Å, °)

N1—C71.282 (2)C3—C41.380 (3)
N1—N21.372 (2)C3—H30.9300
C1—N21.359 (2)C4—H40.9300
C1—C61.413 (3)C7—C101.496 (3)
C1—C21.411 (2)C7—C81.488 (3)
N2—H2A0.888 (9)C8—C91.471 (3)
C2—C31.355 (2)C8—H8A0.9700
C2—H20.9300C8—H8B0.9700
C6—C51.387 (3)C10—H10A0.9600
C6—N31.438 (2)C10—H10B0.9600
C5—C41.356 (3)C10—H10C0.9600
C5—H50.9300C9—H9A0.9600
N3—O11.223 (2)C9—H9B0.9600
N3—O21.227 (2)C9—H9C0.9600
C7—N1—N2116.33 (18)C5—C4—H4120.3
N2—C1—C6123.67 (17)C3—C4—H4120.3
N2—C1—C2120.49 (18)N1—C7—C10125.6 (2)
C6—C1—C2115.84 (18)N1—C7—C8117.5 (2)
C1—N2—N1119.87 (16)C10—C7—C8116.8 (2)
C1—N2—H2A120.1 (14)C9—C8—C7115.8 (2)
N1—N2—H2A120.0 (14)C9—C8—H8A108.3
C3—C2—C1121.61 (18)C7—C8—H8A108.3
C3—C2—H2119.2C9—C8—H8B108.3
C1—C2—H2119.2C7—C8—H8B108.3
C5—C6—C1121.30 (17)H8A—C8—H8B107.4
C5—C6—N3117.42 (19)C7—C10—H10A109.5
C1—C6—N3121.28 (19)C7—C10—H10B109.5
C4—C5—C6120.57 (19)H10A—C10—H10B109.5
C4—C5—H5119.7C7—C10—H10C109.5
C6—C5—H5119.7H10A—C10—H10C109.5
O1—N3—O2121.1 (2)H10B—C10—H10C109.5
O1—N3—C6119.0 (2)C8—C9—H9A109.5
O2—N3—C6119.9 (2)C8—C9—H9B109.5
C2—C3—C4121.22 (18)H9A—C9—H9B109.5
C2—C3—H3119.4C8—C9—H9C109.5
C4—C3—H3119.4H9A—C9—H9C109.5
C5—C4—C3119.5 (2)H9B—C9—H9C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.89 (2)1.97 (2)2.604 (3)127 (1)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2581).

References

  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA. AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • 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]

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