N-(6-Methyl-2-pyrid-yl)formamide.

The mol-ecule of the title compound, C(7)H(8)N(2)O, 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 mol-ecules into centrosymmetric dimers.

Related literature

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

Crystal data

C7H8N2O

M = 136.15

Triclinic,

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 ▶) 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 ▶); cell refinement: XSCANS; 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; software used to prepare material for publication: SHELXTL.

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

C7H8N2O	Z = 2
Mr = 136.15	F(000) = 144
Triclinic, P1	Dx = 1.282 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.0611 (6) Å	Cell parameters from 23 reflections
b = 8.6232 (12) Å	θ = 8.8–16.8°
c = 10.3231 (12) Å	µ = 0.09 mm−1
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

Bruker P4 diffractometer	993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 25.0°, θmin = 4.6°
ω scans	h = −4→1
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = −10→10
Tmin = 0.713, Tmax = 0.940	l = −12→12
1757 measured reflections	3 standard reflections every 97 reflections
1222 independent reflections	intensity decay: none

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-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 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O	1.4562 (3)	0.34810 (14)	0.62540 (13)	0.0766 (5)
N1	1.1428 (3)	0.58235 (15)	0.62843 (12)	0.0528 (4)
H1A	1.2438	0.6042	0.5501	0.063*
N2	0.7461 (3)	0.66352 (15)	0.81236 (13)	0.0509 (4)
C1	0.3445 (5)	0.7290 (3)	1.01096 (18)	0.0728 (6)
H1B	0.3774	0.6176	1.0235	0.109*	0.50
H1C	0.1076	0.7634	1.0212	0.109*	0.50
H1D	0.4388	0.7780	1.0751	0.109*	0.50
H1E	0.2384	0.8217	1.0564	0.109*	0.50
H1F	0.5083	0.6759	1.0587	0.109*	0.50
H1G	0.1771	0.6613	1.0048	0.109*	0.50
C2	0.5164 (4)	0.77275 (19)	0.87483 (16)	0.0553 (5)
C3	0.4394 (5)	0.9158 (2)	0.8175 (2)	0.0685 (5)
H3A	0.2829	0.9906	0.8637	0.082*
C4	0.5969 (5)	0.9474 (2)	0.6904 (2)	0.0717 (6)
H4A	0.5462	1.0435	0.6498	0.086*
C5	0.8283 (4)	0.8360 (2)	0.62478 (18)	0.0609 (5)
H5A	0.9351	0.8536	0.5385	0.073*
C6	0.8977 (4)	0.69680 (18)	0.69102 (15)	0.0480 (4)
C7	1.2323 (4)	0.4432 (2)	0.67961 (16)	0.0621 (5)
H7A	1.1165	0.4164	0.7624	0.075*

	U11	U22	U33	U12	U13	U23
O	0.0884 (9)	0.0587 (8)	0.0646 (8)	0.0094 (7)	0.0201 (7)	0.0038 (6)
N1	0.0586 (8)	0.0521 (8)	0.0424 (7)	−0.0075 (6)	0.0051 (6)	0.0000 (6)
N2	0.0505 (8)	0.0535 (8)	0.0467 (7)	−0.0083 (6)	−0.0011 (6)	−0.0051 (6)
C1	0.0666 (11)	0.0840 (13)	0.0597 (11)	−0.0036 (9)	0.0098 (9)	−0.0148 (9)
C2	0.0468 (9)	0.0588 (9)	0.0589 (10)	−0.0068 (7)	−0.0031 (7)	−0.0124 (8)
C3	0.0574 (10)	0.0579 (10)	0.0857 (13)	−0.0004 (8)	−0.0027 (9)	−0.0137 (9)
C4	0.0680 (11)	0.0529 (10)	0.0918 (14)	−0.0039 (8)	−0.0123 (10)	0.0086 (9)
C5	0.0616 (10)	0.0566 (10)	0.0630 (10)	−0.0121 (8)	−0.0061 (8)	0.0095 (8)
C6	0.0463 (8)	0.0500 (9)	0.0479 (8)	−0.0112 (7)	−0.0046 (6)	−0.0036 (7)
C7	0.0702 (11)	0.0563 (10)	0.0493 (9)	−0.0014 (8)	0.0121 (8)	0.0035 (7)

O—C7	1.2192 (19)	C1—H1F	0.9600
N1—C7	1.327 (2)	C1—H1G	0.9600
N1—C6	1.402 (2)	C2—C3	1.371 (3)
N1—H1A	0.8600	C3—C4	1.380 (3)
N2—C6	1.325 (2)	C3—H3A	0.9300
N2—C2	1.339 (2)	C4—C5	1.368 (3)
C1—C2	1.502 (2)	C4—H4A	0.9300
C1—H1B	0.9600	C5—C6	1.380 (2)
C1—H1C	0.9600	C5—H5A	0.9300
C1—H1D	0.9600	C7—H7A	0.9300
C1—H1E	0.9600
C7—N1—C6	125.62 (13)	H1D—C1—H1G	141.1
C7—N1—H1A	117.2	H1E—C1—H1G	109.5
C6—N1—H1A	117.2	H1F—C1—H1G	109.5
C6—N2—C2	117.87 (15)	N2—C2—C3	122.02 (16)
C2—C1—H1B	109.5	N2—C2—C1	116.18 (15)
C2—C1—H1C	109.5	C3—C2—C1	121.80 (16)
H1B—C1—H1C	109.5	C2—C3—C4	119.19 (17)
C2—C1—H1D	109.5	C2—C3—H3A	120.4
H1B—C1—H1D	109.5	C4—C3—H3A	120.4
H1C—C1—H1D	109.5	C5—C4—C3	119.38 (17)
C2—C1—H1E	109.5	C5—C4—H4A	120.3
H1B—C1—H1E	141.1	C3—C4—H4A	120.3
H1C—C1—H1E	56.3	C4—C5—C6	117.69 (17)
H1D—C1—H1E	56.3	C4—C5—H5A	121.2
C2—C1—H1F	109.5	C6—C5—H5A	121.2
H1B—C1—H1F	56.3	N2—C6—C5	123.81 (16)
H1C—C1—H1F	141.1	N2—C6—N1	117.00 (14)
H1D—C1—H1F	56.3	C5—C6—N1	119.19 (14)
H1E—C1—H1F	109.5	O—C7—N1	124.40 (15)
C2—C1—H1G	109.5	O—C7—H7A	117.8
H1B—C1—H1G	56.3	N1—C7—H7A	117.8
H1C—C1—H1G	56.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Oi	0.86	2.04	2.8971 (19)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Oi	0.86	2.04	2.8971 (19)	172

Symmetry code: (i) .