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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o180.
Published online 2009 December 16. doi:  10.1107/S1600536809053549
PMCID: PMC2980114

N-(6-Methyl-2-pyrid­yl)formamide

Abstract

The mol­ecule of the title compound, C7H8N2O, is essentially planar with a maximum deviation of 0.0439 (1) Å from the best plane. In the crystal, N—H(...)O hydrogen bonds between self-complementary amide groups join mol­ecules into centrosymmetric dimers.

Related literature

For the synthesis of the title compound, see: Hosmane et al. (1984 [triangle]). For background to this work, see: Wang et al. (2006 [triangle]). For the structure of 2-pyridylformamide, see: Bock et al. (1996 [triangle]).

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Object name is e-66-0o180-scheme1.jpg

Experimental

Crystal data

  • C7H8N2O
  • M r = 136.15
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o180-efi1.jpg
  • a = 4.0611 (6) Å
  • b = 8.6232 (12) Å
  • c = 10.3231 (12) Å
  • α = 87.421 (12)°
  • β = 79.344 (14)°
  • γ = 83.103 (15)°
  • V = 352.61 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.5 × 0.2 × 0.1 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: ψ scan(XSCANS; Siemens, 1995 [triangle]) T min = 0.713, T max = 0.940
  • 1757 measured reflections
  • 1222 independent reflections
  • 993 reflections with I > 2σ(I)
  • R int = 0.031
  • 3 standard reflections every 97 reflections
  • intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.148
  • S = 1.05
  • 1222 reflections
  • 92 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: XSCANS (Siemens, 1995 [triangle]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053549/gk2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053549/gk2247Isup2.hkl

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

Acknowledgments

We are grateful to the National Science Council of the Republic of China for support. This research was also supported by the project of the specific research fields in Chung-Yuan Christian University, Taiwan, under grant No. CYCU-98-CR—CH.

supplementary crystallographic information

Comment

A series of Ag(I) coordination polymers containg 2-aminopyrimidine or 2-amino-4,6-dimethylpyrimidine ligands have been prepared, which show one-dimensional and two-dimensional structures (Wang, et al., 2006) with interesting bonding modes. To investigate the effect of flexibility of the ligand on the structural type of such coordination polymers, we have synthesized the title compound. Within this project its crystal structure was determined.

The title molecule is almost planar (Fig. 1). In the crystal structure weak intermolecular N—H···O hydrogen bonding is found between self-complementary amide groups (Table 1) that connects molecules into centrosymmetric dimers. In 2-pyridylformamide the molecules formed dimers via hydrogen bonds between self-complementary 2-pyridylamino groups (Bock et al., 1996).

Experimental

The title compound was prepared according to a procedure reported for N-(2-pyrimidinyl)formamide by Hosmane et al. (1984). Coloress plate crystals suitable for X-ray crystallography were obtained by dissolving the title compound in CH2Cl2, followed by allowing the solution to evaporate slowly under air.

Refinement

All the hydrogen atoms were placed into idealized positions and constrained by the riding atom approximation with C—H = 0.93 — 0.96 Å, N—H = 0.86 Å and Uiso(H) = 1.5 Ueq(C) or 1.2 Ueq(C, N). The methyl H atoms are disordered and were refined in two different orientations.

Figures

Fig. 1.
Molecular structure of the title compound with atom labeling and displacement ellipsoids drawn at the 30% probability level. The disorder is shown with open bonds.

Crystal data

C7H8N2OZ = 2
Mr = 136.15F(000) = 144
Triclinic, P1Dx = 1.282 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.0611 (6) ÅCell parameters from 23 reflections
b = 8.6232 (12) Åθ = 8.8–16.8°
c = 10.3231 (12) ŵ = 0.09 mm1
α = 87.421 (12)°T = 295 K
β = 79.344 (14)°Plate, colorless
γ = 83.103 (15)°0.5 × 0.2 × 0.1 mm
V = 352.61 (8) Å3

Data collection

Bruker P4 diffractometer993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 25.0°, θmin = 4.6°
ω scansh = −4→1
Absorption correction: ψ scan (XSCANS; Siemens, 1995)k = −10→10
Tmin = 0.713, Tmax = 0.940l = −12→12
1757 measured reflections3 standard reflections every 97 reflections
1222 independent reflections intensity decay: none

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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0874P)2 + 0.0372P] where P = (Fo2 + 2Fc2)/3
1222 reflections(Δ/σ)max < 0.001
92 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

Experimental. 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.
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*/UeqOcc. (<1)
O1.4562 (3)0.34810 (14)0.62540 (13)0.0766 (5)
N11.1428 (3)0.58235 (15)0.62843 (12)0.0528 (4)
H1A1.24380.60420.55010.063*
N20.7461 (3)0.66352 (15)0.81236 (13)0.0509 (4)
C10.3445 (5)0.7290 (3)1.01096 (18)0.0728 (6)
H1B0.37740.61761.02350.109*0.50
H1C0.10760.76341.02120.109*0.50
H1D0.43880.77801.07510.109*0.50
H1E0.23840.82171.05640.109*0.50
H1F0.50830.67591.05870.109*0.50
H1G0.17710.66131.00480.109*0.50
C20.5164 (4)0.77275 (19)0.87483 (16)0.0553 (5)
C30.4394 (5)0.9158 (2)0.8175 (2)0.0685 (5)
H3A0.28290.99060.86370.082*
C40.5969 (5)0.9474 (2)0.6904 (2)0.0717 (6)
H4A0.54621.04350.64980.086*
C50.8283 (4)0.8360 (2)0.62478 (18)0.0609 (5)
H5A0.93510.85360.53850.073*
C60.8977 (4)0.69680 (18)0.69102 (15)0.0480 (4)
C71.2323 (4)0.4432 (2)0.67961 (16)0.0621 (5)
H7A1.11650.41640.76240.075*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O0.0884 (9)0.0587 (8)0.0646 (8)0.0094 (7)0.0201 (7)0.0038 (6)
N10.0586 (8)0.0521 (8)0.0424 (7)−0.0075 (6)0.0051 (6)0.0000 (6)
N20.0505 (8)0.0535 (8)0.0467 (7)−0.0083 (6)−0.0011 (6)−0.0051 (6)
C10.0666 (11)0.0840 (13)0.0597 (11)−0.0036 (9)0.0098 (9)−0.0148 (9)
C20.0468 (9)0.0588 (9)0.0589 (10)−0.0068 (7)−0.0031 (7)−0.0124 (8)
C30.0574 (10)0.0579 (10)0.0857 (13)−0.0004 (8)−0.0027 (9)−0.0137 (9)
C40.0680 (11)0.0529 (10)0.0918 (14)−0.0039 (8)−0.0123 (10)0.0086 (9)
C50.0616 (10)0.0566 (10)0.0630 (10)−0.0121 (8)−0.0061 (8)0.0095 (8)
C60.0463 (8)0.0500 (9)0.0479 (8)−0.0112 (7)−0.0046 (6)−0.0036 (7)
C70.0702 (11)0.0563 (10)0.0493 (9)−0.0014 (8)0.0121 (8)0.0035 (7)

Geometric parameters (Å, °)

O—C71.2192 (19)C1—H1F0.9600
N1—C71.327 (2)C1—H1G0.9600
N1—C61.402 (2)C2—C31.371 (3)
N1—H1A0.8600C3—C41.380 (3)
N2—C61.325 (2)C3—H3A0.9300
N2—C21.339 (2)C4—C51.368 (3)
C1—C21.502 (2)C4—H4A0.9300
C1—H1B0.9600C5—C61.380 (2)
C1—H1C0.9600C5—H5A0.9300
C1—H1D0.9600C7—H7A0.9300
C1—H1E0.9600
C7—N1—C6125.62 (13)H1D—C1—H1G141.1
C7—N1—H1A117.2H1E—C1—H1G109.5
C6—N1—H1A117.2H1F—C1—H1G109.5
C6—N2—C2117.87 (15)N2—C2—C3122.02 (16)
C2—C1—H1B109.5N2—C2—C1116.18 (15)
C2—C1—H1C109.5C3—C2—C1121.80 (16)
H1B—C1—H1C109.5C2—C3—C4119.19 (17)
C2—C1—H1D109.5C2—C3—H3A120.4
H1B—C1—H1D109.5C4—C3—H3A120.4
H1C—C1—H1D109.5C5—C4—C3119.38 (17)
C2—C1—H1E109.5C5—C4—H4A120.3
H1B—C1—H1E141.1C3—C4—H4A120.3
H1C—C1—H1E56.3C4—C5—C6117.69 (17)
H1D—C1—H1E56.3C4—C5—H5A121.2
C2—C1—H1F109.5C6—C5—H5A121.2
H1B—C1—H1F56.3N2—C6—C5123.81 (16)
H1C—C1—H1F141.1N2—C6—N1117.00 (14)
H1D—C1—H1F56.3C5—C6—N1119.19 (14)
H1E—C1—H1F109.5O—C7—N1124.40 (15)
C2—C1—H1G109.5O—C7—H7A117.8
H1B—C1—H1G56.3N1—C7—H7A117.8
H1C—C1—H1G56.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···Oi0.862.042.8971 (19)172

Symmetry codes: (i) −x+3, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2247).

References

  • Bock, H., Van, T. T. H., Solouki, B., Schödel, H., Artus, G., Herdtweck, E. & Herrmann, W. A. (1996). Liebigs Ann. Chem. pp. 403–407.
  • Hosmane, R. S., Burnett, F. N. & Albert, M. S. (1984). J. Org. Chem.49, 1212–1215.
  • Sheldrick, G. M. (2008). Acta Cryst A64, 112–122. [PubMed]
  • Siemens (1995). XSCANS Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Wang, Y.-H., Chu, K.-L., Chen, H.-C., Yeh, C.-W., Chan, Z.-K., Suen, M.-C., Chen, J.-D. & Wang, J.-C. (2006). CrystEngComm, 8, 84–93.

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