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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2959.
Published online 2009 October 31. doi:  10.1107/S1600536809045024
PMCID: PMC2971159

Methyl 3-(3-pyridylmethyl­ene)carbazate

Abstract

In the crystal of the title compound, C8H9N3O2, mol­ecules are linked by N—H(...)N hydrogen bonds, forming S(7) chains propagating in [010].

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 [triangle]).

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Object name is e-65-o2959-scheme1.jpg

Experimental

Crystal data

  • C8H9N3O2
  • M r = 179.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2959-efi1.jpg
  • a = 10.585 (2) Å
  • b = 10.019 (2) Å
  • c = 16.311 (3) Å
  • V = 1729.8 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.26 × 0.21 × 0.19 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 15411 measured reflections
  • 1984 independent reflections
  • 1794 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.128
  • S = 1.08
  • 1984 reflections
  • 118 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045024/hb5196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045024/hb5196Isup2.hkl

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

Acknowledgments

The authors would like to thank the Science Foundation of Weifang University (No. 2009Z24).

supplementary crystallographic information

Experimental

A mixture of nicotinaldehyde (0.1 mol), and methyl carbazate (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.082 mol, yield 82%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids.

Crystal data

C8H9N3O2Dx = 1.376 Mg m3
Mr = 179.18Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1985 reflections
a = 10.585 (2) Åθ = 3.4–27.5°
b = 10.019 (2) ŵ = 0.10 mm1
c = 16.311 (3) ÅT = 293 K
V = 1729.8 (6) Å3Block, colourless
Z = 80.26 × 0.21 × 0.19 mm
F(000) = 752

Data collection

Bruker SMART CCD diffractometer1794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
graphiteθmax = 27.5°, θmin = 3.1°
ω scansh = −13→13
15411 measured reflectionsk = −13→12
1984 independent reflectionsl = −21→21

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0867P)2 + 0.1822P] where P = (Fo2 + 2Fc2)/3
1984 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.32 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
O20.18815 (8)0.11348 (8)0.57072 (5)0.0433 (2)
C30.35300 (9)−0.17778 (10)0.74434 (7)0.0343 (3)
H3A0.4286−0.13750.72910.041*
N40.48145 (8)−0.43908 (10)0.88319 (6)0.0390 (3)
C50.35393 (9)−0.28611 (10)0.80449 (6)0.0311 (2)
N10.26042 (8)−0.03820 (9)0.65555 (6)0.0372 (2)
H1A0.3336−0.01240.63910.045*
C40.24493 (9)−0.34567 (12)0.83549 (7)0.0377 (3)
H4B0.1656−0.31560.81940.045*
N20.24948 (8)−0.13809 (9)0.71265 (5)0.0345 (2)
C20.15392 (9)0.01936 (10)0.62537 (6)0.0339 (3)
O10.04701 (7)−0.00686 (10)0.64392 (6)0.0541 (3)
C60.46946 (9)−0.33613 (11)0.83129 (6)0.0358 (3)
H6A0.5428−0.29570.81200.043*
C80.37535 (11)−0.49405 (11)0.91219 (7)0.0393 (3)
H8A0.3819−0.56510.94860.047*
C70.25615 (10)−0.44962 (12)0.89025 (7)0.0414 (3)
H7A0.1845−0.48960.91230.050*
C10.08717 (14)0.19038 (13)0.53648 (8)0.0523 (3)
H1B0.12090.25460.49870.078*
H1C0.04300.23590.57960.078*
H1D0.02980.13220.50820.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0420 (5)0.0450 (5)0.0429 (5)0.0031 (3)0.0027 (3)0.0115 (3)
C30.0289 (5)0.0385 (5)0.0355 (5)−0.0040 (4)−0.0007 (4)0.0006 (4)
N40.0315 (5)0.0440 (5)0.0415 (5)0.0086 (4)−0.0001 (4)0.0016 (4)
C50.0289 (5)0.0341 (5)0.0302 (5)−0.0005 (4)−0.0009 (3)−0.0034 (4)
N10.0277 (4)0.0426 (5)0.0413 (5)−0.0042 (3)−0.0005 (3)0.0102 (4)
C40.0257 (5)0.0467 (6)0.0407 (6)−0.0008 (4)−0.0037 (4)0.0042 (4)
N20.0325 (4)0.0364 (5)0.0346 (4)−0.0039 (3)−0.0018 (3)0.0033 (3)
C20.0324 (5)0.0363 (5)0.0330 (5)−0.0018 (4)−0.0015 (4)0.0005 (4)
O10.0284 (4)0.0685 (6)0.0656 (6)−0.0020 (4)−0.0018 (4)0.0220 (5)
C60.0263 (5)0.0430 (6)0.0380 (5)0.0009 (4)0.0026 (4)−0.0003 (4)
C80.0400 (6)0.0373 (5)0.0407 (5)0.0030 (4)−0.0004 (4)0.0038 (4)
C70.0312 (5)0.0465 (6)0.0463 (6)−0.0069 (4)0.0005 (4)0.0064 (5)
C10.0603 (8)0.0478 (6)0.0489 (7)0.0117 (6)−0.0049 (6)0.0102 (5)

Geometric parameters (Å, °)

O2—C21.3472 (13)N1—H1A0.8600
O2—C11.4312 (15)C4—C71.3771 (16)
C3—N21.2752 (13)C4—H4B0.9300
C3—C51.4631 (14)C2—O11.2005 (13)
C3—H3A0.9300C6—H6A0.9300
N4—C81.3373 (14)C8—C71.3850 (15)
N4—C61.3403 (14)C8—H8A0.9300
C5—C61.3920 (13)C7—H7A0.9300
C5—C41.3940 (13)C1—H1B0.9600
N1—C21.3586 (13)C1—H1C0.9600
N1—N21.3719 (12)C1—H1D0.9600
C2—O2—C1115.73 (9)O2—C2—N1108.28 (9)
N2—C3—C5120.59 (9)N4—C6—C5123.96 (9)
N2—C3—H3A119.7N4—C6—H6A118.0
C5—C3—H3A119.7C5—C6—H6A118.0
C8—N4—C6117.44 (9)N4—C8—C7122.77 (10)
C6—C5—C4117.33 (9)N4—C8—H8A118.6
C6—C5—C3118.92 (8)C7—C8—H8A118.6
C4—C5—C3123.73 (8)C4—C7—C8119.29 (10)
C2—N1—N2119.05 (8)C4—C7—H7A120.4
C2—N1—H1A120.5C8—C7—H7A120.4
N2—N1—H1A120.5O2—C1—H1B109.5
C7—C4—C5119.18 (9)O2—C1—H1C109.5
C7—C4—H4B120.4H1B—C1—H1C109.5
C5—C4—H4B120.4O2—C1—H1D109.5
C3—N2—N1115.47 (8)H1B—C1—H1D109.5
O1—C2—O2124.99 (10)H1C—C1—H1D109.5
O1—C2—N1126.73 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···N4i0.862.122.9751 (14)171

Symmetry codes: (i) −x+1, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5196).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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