2-Pyridone: monoclinic polymorph.

The asymmetric unit in the title compound, C(5)H(5)NO, comprises two independent but virtually identical mol-ecules of 2-pyridone, and represents a monoclinic polymorph of the previously reported ortho-rhom-bic (P2(1)2(1)2(1)) form [Penfold (1953 ▶). Acta Cryst.6, 591-600; Ohms et al. (1984 ▶). Z. Kristallogr.169, 185-200; Yang & Craven (1998 ▶). Acta Cryst. B54, 912-920]. The independent mol-ecules are linked into supra-molecular dimers via eight-membered {⋯HNC(O)}(2) amide synthons in contrast to the helical supra-molecular chains, mediated by {⋯HNC(O)} links, found in the ortho-rhom-bic form.

Related literature

For the structure of the ortho­rhom­bic form of 2-pyridone, see: Penfold (1953 ▶); Ohms et al. (1984 ▶); Yang & Craven (1998 ▶). For related studies of co-crystal formation, see: Broker & Tiekink (2007 ▶); Ellis et al. (2009 ▶). For analysis of the geometric structures, see: Spek (2009 ▶).

Experimental

Crystal data

C5H5NO

M = 95.10

Monoclinic,

a = 6.2027 (13) Å

b = 16.327 (4) Å

c = 9.1046 (18) Å

β = 92.242 (7)°

V = 921.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 98 K

0.44 × 0.39 × 0.15 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.840, T max = 1

6582 measured reflections

1903 independent reflections

1724 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.10

1903 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049496/hg2602sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049496/hg2602Isup2.hkl

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

C5H5NO	F(000) = 400
Mr = 95.10	Dx = 1.371 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 3046 reflections
a = 6.2027 (13) Å	θ = 3.3–40.2°
b = 16.327 (4) Å	µ = 0.10 mm−1
c = 9.1046 (18) Å	T = 98 K
β = 92.242 (7)°	Prism, colourless
V = 921.3 (3) Å3	0.44 × 0.39 × 0.15 mm
Z = 8

Rigaku AFC12K/SATURN724 diffractometer	1903 independent reflections
Radiation source: fine-focus sealed tube	1724 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→5
Tmin = 0.840, Tmax = 1	k = −20→20
6582 measured reflections	l = −11→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.275P] where P = (Fo2 + 2Fc2)/3
1903 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.27541 (14)	0.36020 (6)	0.47704 (10)	0.0239 (2)
N1	−0.07408 (17)	0.31779 (7)	0.48531 (12)	0.0201 (3)
H1N	−0.1007	0.3587	0.5450	0.024*
C1	0.1321 (2)	0.30993 (8)	0.43716 (14)	0.0195 (3)
C2	−0.2397 (2)	0.26660 (8)	0.44686 (15)	0.0232 (3)
H2	−0.3795	0.2769	0.4819	0.028*
C3	−0.2074 (2)	0.20065 (8)	0.35857 (15)	0.0236 (3)
H3	−0.3219	0.1641	0.3330	0.028*
C4	0.0019 (2)	0.18832 (8)	0.30615 (14)	0.0224 (3)
H4	0.0289	0.1426	0.2450	0.027*
C5	0.1649 (2)	0.24113 (8)	0.34226 (14)	0.0209 (3)
H5	0.3033	0.2324	0.3039	0.025*
O2	−0.14759 (15)	0.44304 (6)	0.67815 (11)	0.0263 (3)
N2	0.19925 (17)	0.48837 (7)	0.67120 (12)	0.0204 (3)
H2N	0.2238	0.4519	0.6027	0.024*
C6	−0.0049 (2)	0.49182 (8)	0.72495 (14)	0.0199 (3)
C7	−0.0344 (2)	0.55309 (8)	0.83511 (15)	0.0236 (3)
H7	−0.1717	0.5592	0.8765	0.028*
C8	0.1311 (2)	0.60263 (9)	0.88132 (16)	0.0267 (3)
H8	0.1078	0.6427	0.9547	0.032*
C9	0.3370 (2)	0.59536 (9)	0.82168 (17)	0.0276 (3)
H9	0.4526	0.6299	0.8539	0.033*
C10	0.3652 (2)	0.53746 (9)	0.71679 (15)	0.0243 (3)
H10	0.5022	0.5313	0.6751	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0186 (5)	0.0256 (5)	0.0277 (5)	−0.0021 (4)	0.0025 (4)	−0.0048 (4)
N1	0.0186 (6)	0.0198 (5)	0.0219 (5)	0.0010 (4)	0.0027 (4)	−0.0035 (4)
C1	0.0180 (6)	0.0210 (6)	0.0195 (6)	0.0012 (5)	0.0000 (5)	0.0018 (5)
C2	0.0178 (6)	0.0248 (7)	0.0272 (7)	−0.0013 (5)	0.0026 (5)	−0.0022 (5)
C3	0.0208 (7)	0.0220 (7)	0.0281 (7)	−0.0021 (5)	0.0013 (5)	−0.0036 (5)
C4	0.0244 (7)	0.0202 (6)	0.0227 (6)	0.0036 (5)	−0.0004 (5)	−0.0025 (5)
C5	0.0179 (6)	0.0239 (7)	0.0211 (6)	0.0031 (5)	0.0031 (5)	−0.0010 (5)
O2	0.0206 (5)	0.0245 (5)	0.0342 (5)	−0.0041 (4)	0.0062 (4)	−0.0078 (4)
N2	0.0209 (6)	0.0183 (5)	0.0221 (5)	−0.0003 (4)	0.0029 (4)	−0.0014 (4)
C6	0.0191 (6)	0.0183 (6)	0.0222 (6)	0.0011 (5)	0.0009 (5)	0.0029 (5)
C7	0.0212 (6)	0.0252 (7)	0.0245 (7)	0.0031 (5)	0.0025 (5)	−0.0007 (5)
C8	0.0268 (7)	0.0262 (7)	0.0270 (7)	0.0035 (5)	−0.0010 (6)	−0.0063 (5)
C9	0.0227 (7)	0.0256 (7)	0.0342 (8)	−0.0026 (5)	−0.0024 (6)	−0.0043 (6)
C10	0.0176 (6)	0.0251 (7)	0.0304 (7)	−0.0016 (5)	0.0015 (5)	0.0016 (6)

O1—C1	1.2529 (16)	O2—C6	1.2530 (16)
N1—C2	1.3597 (17)	N2—C10	1.3567 (17)
N1—C1	1.3743 (17)	N2—C6	1.3762 (17)
N1—H1N	0.8800	N2—H2N	0.8800
C1—C5	1.4365 (18)	C6—C7	1.4335 (18)
C2—C3	1.3633 (19)	C7—C8	1.3607 (19)
C2—H2	0.9500	C7—H7	0.9500
C3—C4	1.4151 (18)	C8—C9	1.412 (2)
C3—H3	0.9500	C8—H8	0.9500
C4—C5	1.3590 (19)	C9—C10	1.360 (2)
C4—H4	0.9500	C9—H9	0.9500
C5—H5	0.9500	C10—H10	0.9500
C2—N1—C1	124.33 (11)	C10—N2—C6	124.37 (11)
C2—N1—H1N	117.8	C10—N2—H2N	117.8
C1—N1—H1N	117.8	C6—N2—H2N	117.8
O1—C1—N1	120.32 (11)	O2—C6—N2	120.04 (12)
O1—C1—C5	124.83 (12)	O2—C6—C7	124.99 (12)
N1—C1—C5	114.84 (11)	N2—C6—C7	114.96 (11)
N1—C2—C3	120.67 (12)	C8—C7—C6	121.03 (12)
N1—C2—H2	119.7	C8—C7—H7	119.5
C3—C2—H2	119.7	C6—C7—H7	119.5
C2—C3—C4	118.00 (12)	C7—C8—C9	120.93 (13)
C2—C3—H3	121.0	C7—C8—H8	119.5
C4—C3—H3	121.0	C9—C8—H8	119.5
C5—C4—C3	120.77 (12)	C10—C9—C8	118.12 (13)
C5—C4—H4	119.6	C10—C9—H9	120.9
C3—C4—H4	119.6	C8—C9—H9	120.9
C4—C5—C1	121.36 (12)	N2—C10—C9	120.59 (12)
C4—C5—H5	119.3	N2—C10—H10	119.7
C1—C5—H5	119.3	C9—C10—H10	119.7
C2—N1—C1—O1	179.47 (12)	C10—N2—C6—O2	−178.77 (12)
C2—N1—C1—C5	−1.04 (18)	C10—N2—C6—C7	0.61 (18)
C1—N1—C2—C3	2.1 (2)	O2—C6—C7—C8	178.83 (13)
N1—C2—C3—C4	−1.3 (2)	N2—C6—C7—C8	−0.51 (19)
C2—C3—C4—C5	−0.4 (2)	C6—C7—C8—C9	0.2 (2)
C3—C4—C5—C1	1.5 (2)	C7—C8—C9—C10	0.0 (2)
O1—C1—C5—C4	178.72 (12)	C6—N2—C10—C9	−0.4 (2)
N1—C1—C5—C4	−0.74 (18)	C8—C9—C10—N2	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2	0.88	1.86	2.7450 (16)	177
N2—H2n···O1	0.88	1.92	2.7915 (16)	171
C2—H2···O1i	0.95	2.53	3.3943 (18)	150
C4—H4···O2ii	0.95	2.54	3.2989 (18)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2	0.88	1.86	2.7450 (16)	177
N2—H2n⋯O1	0.88	1.92	2.7915 (16)	171
C2—H2⋯O1i	0.95	2.53	3.3943 (18)	150
C4—H4⋯O2ii	0.95	2.54	3.2989 (18)	137

Symmetry codes: (i) ; (ii) .