N-(6-Methyl-2-pyrid­yl)formamide

Hu, H.-L.; Wu, C.-J.; Cheng, P.-C.; Chen, J.-D.

doi:10.1107/S1600536809053549

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o180

doi:10.1107/S1600536809053549

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N-(6-Methyl-2-pyridyl)formamide

Hui-Ling Hu,^a Chia-Jun Wu,^b Pei-Chi Cheng ^b and Jhy-Der Chen ^b ^*

^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 ). 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_r = 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 ) 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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.148
S = 1.05
1222 reflections
92 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) -x+3, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

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.

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

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

C₇H₈N₂O	Z = 2
M_r = 136.15	F(000) = 144
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0874P)² + 0.0372P] where P = (F_o² + 2F_c²)/3
1222 reflections	(Δ/σ)_max < 0.001
92 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₇H₈N₂O	γ = 83.103 (15)°
M_r = 136.15	V = 352.61 (8) Å³
Triclinic, P1	Z = 2
a = 4.0611 (6) Å	Mo Kα radiation
b = 8.6232 (12) Å	µ = 0.09 mm⁻¹
c = 10.3231 (12) Å	T = 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)	R_int = 0.031
T_min = 0.713, T_max = 0.940	3 standard reflections every 97 reflections
1757 measured reflections	intensity decay: none
1222 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
1222 reflections	Δρ_min = −0.16 e Å⁻³
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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₇H₈N₂O
M_r	136.15
Crystal system, space group	Triclinic, 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)
V (Å³)	352.61 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.5 × 0.2 × 0.1

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	ψ scan (XSCANS; Siemens, 1995)
T_min, T_max	0.713, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	1757, 1222, 993
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.148, 1.05
No. of reflections	1222
No. of parameters	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1A···Oⁱ	0.86	2.04	2.8971 (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

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