organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-(6-Methyl-2-pyrid­yl)formamide

aDepartment of Chemical Engineering and Material Engineering, Nanya Institute of Technology, Chung-Li, Taiwan, and bDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li, Taiwan
*Correspondence e-mail: jdchen@cycu.edu.tw

(Received 10 December 2009; accepted 11 December 2009; online 16 December 2009)

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[Hosmane, R. S., Burnett, F. N. & Albert, M. S. (1984). J. Org. Chem. 49, 1212-1215.]). For background to this work, see: Wang et al. (2006[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.]). For the structure of 2-pyridylformamide, see: Bock et al. (1996[Bock, H., Van, T. T. H., Solouki, B., Schödel, H., Artus, G., Herdtweck, E. & Herrmann, W. A. (1996). Liebigs Ann. Chem. pp. 403-407.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8N2O

  • Mr = 136.15

  • Triclinic, [P \overline 1]

  • 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[Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.713, Tmax = 0.940

  • 1757 measured reflections

  • 1222 independent reflections

  • 993 reflections with I > 2σ(I)

  • Rint = 0.031

  • 3 standard reflections every 97 reflections

  • intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯Oi 0.86 2.04 2.8971 (19) 172
Symmetry code: (i) -x+3, -y+1, -z+1.

Data collection: XSCANS (Siemens, 1995[Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
N-(6-Methyl-2-pyridyl)formamide top
Crystal data top
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 top
Bruker P4
diffractometer
993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 25.0°, θmin = 4.6°
ω scansh = 41
Absorption correction: ψ scan
(XSCANS; Siemens, 1995)
k = 1010
Tmin = 0.713, Tmax = 0.940l = 1212
1757 measured reflections3 standard reflections every 97 reflections
1222 independent reflections intensity decay: none
Refinement top
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 = 1.05 w = 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
Crystal data top
C7H8N2Oγ = 83.103 (15)°
Mr = 136.15V = 352.61 (8) Å3
Triclinic, P1Z = 2
a = 4.0611 (6) ÅMo Kα radiation
b = 8.6232 (12) ŵ = 0.09 mm1
c = 10.3231 (12) ÅT = 295 K
α = 87.421 (12)°0.5 × 0.2 × 0.1 mm
β = 79.344 (14)°
Data collection top
Bruker P4
diffractometer
993 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XSCANS; Siemens, 1995)
Rint = 0.031
Tmin = 0.713, Tmax = 0.9403 standard reflections every 97 reflections
1757 measured reflections intensity decay: none
1222 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.05Δρmax = 0.15 e Å3
1222 reflectionsΔρmin = 0.16 e Å3
92 parameters
Special details top

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) top
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) top
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) top
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, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Oi0.862.042.8971 (19)172
Symmetry code: (i) x+3, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC7H8N2O
Mr136.15
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)4.0611 (6), 8.6232 (12), 10.3231 (12)
α, β, γ (°)87.421 (12), 79.344 (14), 83.103 (15)
V3)352.61 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.5 × 0.2 × 0.1
Data collection
DiffractometerBruker P4
diffractometer
Absorption correctionψ scan
(XSCANS; Siemens, 1995)
Tmin, Tmax0.713, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
1757, 1222, 993
Rint0.031
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.148, 1.05
No. of reflections1222
No. of parameters92
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: XSCANS (Siemens, 1995), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Oi0.862.042.8971 (19)172.1
Symmetry code: (i) x+3, y+1, z+1.
 

Acknowledgements

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.

References

First citationBock, H., Van, T. T. H., Solouki, B., Schödel, H., Artus, G., Herdtweck, E. & Herrmann, W. A. (1996). Liebigs Ann. Chem. pp. 403–407.  Google Scholar
First citationHosmane, R. S., Burnett, F. N. & Albert, M. S. (1984). J. Org. Chem. 49, 1212–1215.  CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationWang, 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.  CAS Google Scholar

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ISSN: 2056-9890
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