5-Methyl-2-pyridone

Mao, S.; Yanghui, L.; Meiling, P.

doi:10.1107/S1600536811033484

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2440

doi:10.1107/S1600536811033484

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5-Methyl-2-pyridone

Shulin Mao,^a ^* Luo Yanghui ^a and Pan Meiling ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 7 August 2011; accepted 17 August 2011; online 27 August 2011)

The crystal structure of the title compound, C₆H₇NO, is stabilized by intermolecular N—H⋯O hydrogen bonds, resulting in inversion dimers. The structure is further consolidated by weak C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Boris-Marko et al. (2008 ); Vovk et al. (2003 ).

Experimental

Crystal data

C₆H₇NO
M_r = 109.13
Monoclinic, C 2/c
a = 12.965 (3) Å
b = 9.7154 (19) Å
c = 10.908 (2) Å
β = 118.96 (3)°
V = 1202.3 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.23 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.977, T_max = 0.984
5961 measured reflections
1369 independent reflections
670 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.163
S = 0.99
1369 reflections
73 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	1.94	2.800 (2)	173
C3—H3A⋯O1ⁱⁱ	0.93	2.46	3.334 (3)	157
C5—H5A⋯O1ⁱⁱⁱ	0.93	2.33	3.260 (3)	178
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811033484/pv2442sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033484/pv2442Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033484/pv2442Isup3.cml

checkCIF report

Comment top

The title compound is characterized by an enol-keto tautomerism due to the labile hydrogen atom of OH-group in α-position to the basic pyridine N atom which can easily migrate to N atom (Boris-Marko et al., 2008) resulting in a zwitterionic molecule (Fig. 1).

The O1 and C6 atoms located on the pyridine ring are conplanar with the ring, deviating by 0.0.15 (3) and 0.35 (4) Å, respectively, from the ring plane, The crystal structure is stabilized by intermolecular N—H···O hydrogen bonds and further consolidated by C—H···O interactions (Fig.e 2 and Tab. 1).

Related literature top

For related structures, see: Boris-Marko et al. (2008); Vovk et al. (2003).

Experimental top

To a solution of the title compounde (0.2 g) in acetone (2 ml) and ethanol (10 ml) was added was prepared by stirred at room temperature and then placed in a dark place. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of the solution over a period of 8 d.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. An ORTEP view of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Unit cell packing of the title compound showing H-bonding interactions.

5-Methyl-2-pyridone top

Crystal data top

C₆H₇NO	F(000) = 464
M_r = 109.13	D_x = 1.206 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1369 reflections
a = 12.965 (3) Å	θ = 3.6–27.5°
b = 9.7154 (19) Å	µ = 0.08 mm⁻¹
c = 10.908 (2) Å	T = 293 K
β = 118.96 (3)°	Prism, colourless
V = 1202.3 (4) Å³	0.30 × 0.23 × 0.20 mm
Z = 8

Data collection top

Rigaku SCXmini diffractometer	1369 independent reflections
Radiation source: fine-focus sealed tube	670 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.6°
CCD_Profile_fitting scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.977, T_max = 0.984	l = −14→14
5961 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0734P)²] where P = (F_o² + 2F_c²)/3
1369 reflections	(Δ/σ)_max < 0.001
73 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₆H₇NO	V = 1202.3 (4) Å³
M_r = 109.13	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.965 (3) Å	µ = 0.08 mm⁻¹
b = 9.7154 (19) Å	T = 293 K
c = 10.908 (2) Å	0.30 × 0.23 × 0.20 mm
β = 118.96 (3)°

Data collection top

Rigaku SCXmini diffractometer	1369 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	670 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.049
5961 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 0.99	Δρ_max = 0.12 e Å⁻³
1369 reflections	Δρ_min = −0.17 e Å⁻³
73 parameters

Special details top

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
N1	0.28530 (13)	0.79540 (16)	0.17990 (16)	0.0616 (5)
H1A	0.3148	0.7521	0.1353	0.074*
O1	0.11700 (11)	0.82537 (15)	−0.02634 (14)	0.0730 (5)
C1	0.17371 (17)	0.8437 (2)	0.1049 (2)	0.0600 (6)
C2	0.13100 (19)	0.9133 (2)	0.1852 (2)	0.0718 (7)
H2A	0.0549	0.9488	0.1410	0.086*
C5	0.35432 (18)	0.8107 (2)	0.3216 (2)	0.0672 (6)
H5A	0.4300	0.7740	0.3655	0.081*
C4	0.3147 (2)	0.8781 (2)	0.3988 (2)	0.0665 (6)
C3	0.1989 (2)	0.9291 (2)	0.3250 (2)	0.0750 (7)
H3A	0.1679	0.9755	0.3743	0.090*
C6	0.3897 (2)	0.8989 (2)	0.5532 (3)	0.0978 (9)
H6A	0.4652	0.8566	0.5840	0.147*
H6B	0.3520	0.8578	0.6013	0.147*
H6C	0.4000	0.9956	0.5734	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0493 (10)	0.0718 (12)	0.0626 (11)	0.0060 (8)	0.0263 (9)	−0.0035 (8)
O1	0.0544 (9)	0.1007 (12)	0.0615 (11)	0.0047 (7)	0.0262 (8)	0.0016 (8)
C1	0.0469 (12)	0.0662 (13)	0.0683 (15)	0.0002 (9)	0.0290 (12)	0.0079 (11)
C2	0.0635 (13)	0.0820 (16)	0.0773 (17)	0.0145 (11)	0.0401 (14)	0.0034 (12)
C5	0.0574 (13)	0.0666 (14)	0.0704 (15)	−0.0003 (10)	0.0252 (12)	−0.0006 (11)
C4	0.0713 (15)	0.0644 (14)	0.0624 (15)	−0.0024 (11)	0.0312 (13)	−0.0048 (11)
C3	0.0834 (17)	0.0739 (15)	0.0807 (18)	0.0098 (12)	0.0500 (15)	−0.0020 (12)
C6	0.109 (2)	0.102 (2)	0.0722 (18)	−0.0037 (14)	0.0354 (17)	−0.0110 (13)

Geometric parameters (Å, º) top

N1—C1	1.355 (2)	C5—H5A	0.9300
N1—C5	1.368 (2)	C4—C3	1.406 (3)
N1—H1A	0.8600	C4—C6	1.496 (3)
O1—C1	1.266 (2)	C3—H3A	0.9300
C1—C2	1.414 (3)	C6—H6A	0.9600
C2—C3	1.351 (3)	C6—H6B	0.9600
C2—H2A	0.9300	C6—H6C	0.9600
C5—C4	1.350 (3)

C1—N1—C5	124.56 (18)	C5—C4—C3	115.9 (2)
C1—N1—H1A	117.7	C5—C4—C6	122.1 (2)
C5—N1—H1A	117.7	C3—C4—C6	122.0 (2)
O1—C1—N1	119.97 (19)	C2—C3—C4	122.6 (2)
O1—C1—C2	125.48 (19)	C2—C3—H3A	118.7
N1—C1—C2	114.55 (19)	C4—C3—H3A	118.7
C3—C2—C1	121.1 (2)	C4—C6—H6A	109.5
C3—C2—H2A	119.4	C4—C6—H6B	109.5
C1—C2—H2A	119.4	H6A—C6—H6B	109.5
C4—C5—N1	121.30 (19)	C4—C6—H6C	109.5
C4—C5—H5A	119.3	H6A—C6—H6C	109.5
N1—C5—H5A	119.3	H6B—C6—H6C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	1.94	2.800 (2)	173
C3—H3A···O1ⁱⁱ	0.93	2.46	3.334 (3)	157
C5—H5A···O1ⁱⁱⁱ	0.93	2.33	3.260 (3)	178

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

Experimental details

Crystal data
Chemical formula	C₆H₇NO
M_r	109.13
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	12.965 (3), 9.7154 (19), 10.908 (2)
β (°)	118.96 (3)
V (Å³)	1202.3 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.23 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	5961, 1369, 670
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.163, 0.99
No. of reflections	1369
No. of parameters	73
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.17

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	1.94	2.800 (2)	173
C3—H3A···O1ⁱⁱ	0.93	2.46	3.334 (3)	157
C5—H5A···O1ⁱⁱⁱ	0.93	2.33	3.260 (3)	178

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Project 20671019)

References

Boris-Marko, K., Popović, Z., Pavlović, G. & Rajić-Linarić, M. (2008). J. Mol. Struct. 882, 47–55. Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact. GbR, Bonn, Germany. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vovk, T. V., Kovalchukova, O. V., Zaitsev, B. E., Strashnova, S. B., Belskii, V. K. & Stash, A. L. (2003). Koord. Khim. 29, 312–314. Google Scholar