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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o373.
Published online 2009 January 23. doi:  10.1107/S1600536809002256
PMCID: PMC2968229

2-Chloro­pyridine-3-carboxamide

Abstract

In the crystal structure of the title compound, C6H5ClN2O, the dihedral angle between the pyridine ring and the carboxamine group is 63.88 (8)°. Inter­molecular N—H(...)N and N—H(...)O hydrogen bonds link the mol­ecules into a two-dimensional network.

Related literature

Details of applications of the title compound can be found in: Oda et al. (1993 [triangle]); Qin et al. (2001 [triangle]).

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Object name is e-65-0o373-scheme1.jpg

Experimental

Crystal data

  • C6H5ClN2O
  • M r = 156.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o373-efi1.jpg
  • a = 6.980 (5) Å
  • b = 13.627 (9) Å
  • c = 7.108 (5) Å
  • β = 91.82 (5)°
  • V = 675.8 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.49 mm−1
  • T = 293 (2) K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.868, T max = 0.909
  • 2716 measured reflections
  • 1188 independent reflections
  • 1083 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.096
  • S = 1.11
  • 1188 reflections
  • 92 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002256/nc2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002256/nc2131Isup2.hkl

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

Acknowledgments

The authors thank the SNSFC (grant No. 2008011021), the Foundation for Returned Overseas Chinese Scholars of Shanxi Province and Shanxi Key Laboratory Foundation for financial support, and the Youth Foundation of Shanxi University, China (grant No. 2006026).

supplementary crystallographic information

Comment

The structure of 2-chloropyridine-3-carboxamide has attracted us owing to its fungicidal activities (Oda et al., 1993) and its application in coordination chemistry (Qin et al., 2001). The dihedral angles formed by the pyridine ring and the carboxamine group amount to 63.88 (8)° (Fig. 1). The molecules are connected via intermolecular N—H···N and N—H···O hydrogen bonding into layers, with H···N distances of 2.21 and O···H distances of 2.17 Å (Fig. 2 and Tab. 1).

Experimental

Ammonia (10 ml, 66 mmol, 25%) was added slowly to a solution of 2-chloropyridine-3-carbonyl chloride (4.0 g, 22 mmol) in THF (20 ml) at 0°C. The reaction mixture was allowed to warm up to room temperature and stirred for 1.5 h. The resulting mixture was dried under vacuum and washed with two 20 ml portions of THF. Then the solution was dried over anhydrous magnesium sulfate. The solvent was removed by vacuum, and the product was collected, yield: 1.93 g, 56%; m.p. 162.5°C. The crystal suitable for X-ray analysis was grown by slow evaporation of the solvent from a diethyl ether solution at 20°. Anal. Calcd for C6H5ClN2O: C, 45.97; H, 3.14; N, 17.82%. Found: C, 46.03; H, 3.22; N, 17.89%.

Refinement

All H atoms were positioned with idealized geometry, with C—H = 0.96 and N—H = 0.86 Å, and were refined with Uiso(H) values set to 1.2 Ueq(C,N).

Figures

Fig. 1.
View of the molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal structure of the title compound along [100] with intermolecular N—H···N and N—H···O hydrogen bonding shown as dashed lines.

Crystal data

C6H5ClN2OF(000) = 320
Mr = 156.57Dx = 1.539 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.980 (5) ÅCell parameters from 1764 reflections
b = 13.627 (9) Åθ = 2.9–26.9°
c = 7.108 (5) ŵ = 0.49 mm1
β = 91.82 (5)°T = 293 K
V = 675.8 (8) Å3Plate, yellow
Z = 40.30 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer1188 independent reflections
Radiation source: fine-focus sealed tube1083 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −8→6
Tmin = 0.868, Tmax = 0.909k = −15→16
2716 measured reflectionsl = −6→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.096w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1035P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
1188 reflectionsΔρmax = 0.18 e Å3
92 parametersΔρmin = −0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.051 (8)

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
Cl0.14993 (7)0.10791 (4)0.88571 (7)0.0533 (2)
C10.3716 (2)0.07827 (13)0.7965 (2)0.0349 (4)
N10.4064 (2)−0.01655 (11)0.7824 (2)0.0446 (4)
O0.5546 (2)0.30761 (9)0.8932 (2)0.0507 (4)
C60.4574 (2)0.25974 (12)0.7786 (2)0.0351 (4)
N20.3180 (2)0.29749 (11)0.6708 (2)0.0446 (4)
H2A0.29090.35890.67860.054*
H2B0.25450.26060.59300.054*
C30.6760 (3)0.12278 (14)0.6910 (3)0.0430 (5)
H30.76810.16920.66160.052*
C40.7153 (3)0.02376 (16)0.6735 (3)0.0505 (5)
H40.83310.00260.63120.061*
C20.4989 (2)0.15240 (12)0.7524 (2)0.0325 (4)
C50.5774 (3)−0.04231 (14)0.7198 (3)0.0506 (6)
H50.6042−0.10880.70710.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl0.0357 (3)0.0599 (4)0.0647 (4)−0.0034 (2)0.0066 (2)0.0116 (2)
C10.0347 (9)0.0346 (9)0.0350 (9)−0.0023 (7)−0.0060 (7)0.0017 (7)
N10.0541 (10)0.0302 (8)0.0485 (9)−0.0029 (7)−0.0125 (8)0.0009 (6)
O0.0548 (9)0.0356 (7)0.0603 (9)−0.0041 (6)−0.0181 (7)−0.0060 (6)
C60.0333 (9)0.0319 (9)0.0399 (9)−0.0025 (7)−0.0003 (7)0.0020 (7)
N20.0456 (9)0.0300 (8)0.0573 (10)0.0039 (6)−0.0124 (8)−0.0020 (7)
C30.0336 (10)0.0493 (12)0.0460 (10)0.0009 (8)−0.0022 (8)−0.0017 (8)
C40.0431 (11)0.0566 (13)0.0512 (12)0.0162 (9)−0.0069 (9)−0.0109 (9)
C20.0298 (9)0.0335 (9)0.0337 (9)0.0002 (7)−0.0051 (7)−0.0002 (7)
C50.0649 (14)0.0346 (10)0.0509 (11)0.0130 (9)−0.0191 (10)−0.0081 (8)

Geometric parameters (Å, °)

Cl—C11.738 (2)N2—H2B0.8600
C1—N11.319 (2)C3—C41.383 (3)
C1—C21.388 (3)C3—C21.385 (3)
N1—C51.334 (3)C3—H30.9300
O—C61.230 (2)C4—C51.366 (3)
C6—N21.324 (2)C4—H40.9300
C6—C21.504 (3)C5—H50.9300
N2—H2A0.8600
N1—C1—C2125.08 (18)C4—C3—H3120.2
N1—C1—Cl115.07 (14)C2—C3—H3120.2
C2—C1—Cl119.80 (14)C5—C4—C3118.6 (2)
C1—N1—C5116.88 (16)C5—C4—H4120.7
O—C6—N2123.86 (17)C3—C4—H4120.7
O—C6—C2119.55 (15)C3—C2—C1116.34 (17)
N2—C6—C2116.57 (15)C3—C2—C6120.00 (16)
C6—N2—H2A120.0C1—C2—C6123.56 (16)
C6—N2—H2B120.0N1—C5—C4123.49 (18)
H2A—N2—H2B120.0N1—C5—H5118.3
C4—C3—C2119.63 (19)C4—C5—H5118.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.862.213.003 (3)154
N2—H2B···Oii0.862.173.015 (3)168

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2131).

References

  • Oda, M., Sakaki, T., Sasaki, N., Nonaka, H., Yamagishi, K. & Tomita, H. (1993). J. Pestic. Sci.18, 49–57.
  • Qin, Z., Jennings, M. C. & Puddephatt, R. J. (2001). Inorg. Chem.40, 6220–6228. [PubMed]
  • Sheldrick, G. M. (1997). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison Wisconsin, USA.

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