Crystal structure of 2,6-dimethyl-4-pyridone hemihydrate.

The title compound (systematic name: 2,6-dimethyl-1H-pyridin-4-one hemihydrate), C7H9NO·0.5H2O, has a single planar mol-ecule in the asymmetric unit with the non-H atoms possessing a mean deviation from planarity of 0.021 Å. There is also half of a water mol-ecule present in the asymmetric unit. In the crystal, infinite (001) sheets are formed by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the crystal structure of the parent 4-pyridone, see: Jones (2001 ▸); Tyl et al. (2008 ▸). For the title compound bound to zirconium, see: Castillo et al. (1987 ▸). For the structure of a chloro-substituted variant of the title compound, see: Boer (1972 ▸).

Experimental

Crystal data

C7H9NO·0.5H2O

M = 132.16

Orthorhombic,

a = 12.4859 (17) Å

b = 14.3697 (19) Å

c = 7.732 (1) Å

V = 1387.3 (3) Å3

Z = 8

Cu Kα radiation

μ = 0.73 mm−1

T = 120 K

0.5 × 0.1 × 0.1 mm

Data collection

Bruker Venture D8 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.554, T max = 0.754

11786 measured reflections

1366 independent reflections

1352 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.078

S = 1.09

1366 reflections

95 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack x determined using 611 quotients [(I +)-(I -)]/[(I +)+(I -)] (Parsons et al., 2013 ▸.

Absolute structure parameter: 0.05 (12)

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015012402/ff2139sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012402/ff2139Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012402/ff2139Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012402/ff2139fig1.tif

Mol­ecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S2056989015012402/ff2139fig2.tif

Mol­ecular packing of the title compound with hydrogen bonding shown as dashed lines.

CCDC reference: 1409189

Additional supporting information: crystallographic information; 3D view; checkCIF report

C7H9NO·0.5H2O	F(000) = 568
Mr = 132.16	Dx = 1.266 Mg m−3
Orthorhombic, Aba2	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: A 2 -2ac	Cell parameters from 9829 reflections
a = 12.4859 (17) Å	θ = 7.1–72.4°
b = 14.3697 (19) Å	µ = 0.73 mm−1
c = 7.732 (1) Å	T = 120 K
V = 1387.3 (3) Å3	NEEDLE, colourless
Z = 8	0.5 × 0.1 × 0.1 mm

Bruker Venture D8 CMOS diffractometer	1366 independent reflections
Radiation source: microfocus Cu	1352 reflections with I > 2σ(I)
HELIOS MX monochromator	Rint = 0.060
φ and ω scans	θmax = 72.4°, θmin = 7.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −15→15
Tmin = 0.554, Tmax = 0.754	k = −17→17
11786 measured reflections	l = −9→9

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.3383P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.15 e Å−3
1366 reflections	Δρmin = −0.19 e Å−3
95 parameters	Absolute structure: Flack x determined using 611 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013.
3 restraints	Absolute structure parameter: 0.05 (12)

Experimental. Absorption correction: SADABS-2014/4 (Bruker,2014) was used for absorption correction. wR2(int) was 0.1440 before and 0.0881 after correction. The Ratio of minimum to maximum transmission is 0.7350. The λ/2 correction factor is 0.00150.

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.

	x	y	z	Uiso*/Ueq
O1	0.47723 (9)	0.33620 (8)	0.49203 (19)	0.0287 (3)
O2	0.5000	0.5000	0.6889 (3)	0.0399 (5)
N1	0.16883 (11)	0.24949 (11)	0.4446 (2)	0.0215 (3)
C3	0.35308 (14)	0.22232 (12)	0.3962 (2)	0.0234 (4)
H3	0.4083	0.1841	0.3504	0.028*
C2	0.24877 (14)	0.19343 (12)	0.3853 (2)	0.0222 (4)
C4	0.38007 (12)	0.30864 (12)	0.4748 (2)	0.0226 (4)
C7	0.09367 (14)	0.39066 (13)	0.5690 (3)	0.0265 (4)
H7A	0.0630	0.4210	0.4669	0.040*
H7B	0.1158	0.4381	0.6527	0.040*
H7C	0.0399	0.3499	0.6218	0.040*
C6	0.18900 (13)	0.33399 (11)	0.5164 (2)	0.0217 (4)
C1	0.21576 (15)	0.10115 (12)	0.3125 (3)	0.0270 (4)
H1A	0.1736	0.0672	0.3988	0.040*
H1B	0.2797	0.0650	0.2828	0.040*
H1C	0.1724	0.1109	0.2085	0.040*
C5	0.29237 (13)	0.36395 (12)	0.5339 (2)	0.0229 (4)
H5	0.3061	0.4226	0.5862	0.027*
H2	0.4956 (19)	0.4524 (12)	0.621 (3)	0.034*
H1	0.1043 (9)	0.2265 (14)	0.444 (4)	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0205 (5)	0.0250 (6)	0.0405 (8)	−0.0007 (5)	−0.0004 (6)	−0.0028 (6)
O2	0.0553 (14)	0.0318 (11)	0.0324 (11)	−0.0147 (10)	0.000	0.000
N1	0.0206 (6)	0.0206 (7)	0.0234 (7)	−0.0014 (5)	0.0004 (6)	0.0008 (6)
C3	0.0240 (8)	0.0215 (8)	0.0246 (8)	0.0035 (6)	0.0014 (7)	0.0012 (8)
C2	0.0268 (8)	0.0193 (8)	0.0205 (7)	0.0009 (6)	−0.0014 (7)	0.0022 (7)
C4	0.0229 (8)	0.0208 (8)	0.0241 (9)	0.0003 (6)	−0.0011 (7)	0.0038 (8)
C7	0.0245 (8)	0.0243 (8)	0.0309 (10)	0.0025 (7)	−0.0008 (7)	−0.0041 (8)
C6	0.0244 (8)	0.0196 (8)	0.0213 (8)	0.0009 (6)	−0.0012 (7)	0.0019 (7)
C1	0.0309 (9)	0.0216 (8)	0.0284 (10)	−0.0005 (7)	−0.0007 (8)	−0.0012 (8)
C5	0.0255 (8)	0.0174 (7)	0.0258 (8)	−0.0004 (6)	−0.0006 (7)	0.0004 (7)

O1—C4	1.283 (2)	C7—H7A	0.9800
O2—H2	0.862 (7)	C7—H7B	0.9800
N1—C2	1.362 (2)	C7—H7C	0.9800
N1—C6	1.359 (2)	C7—C6	1.498 (2)
N1—H1	0.871 (7)	C6—C5	1.367 (2)
C3—H3	0.9500	C1—H1A	0.9800
C3—C2	1.370 (2)	C1—H1B	0.9800
C3—C4	1.422 (3)	C1—H1C	0.9800
C2—C1	1.498 (2)	C5—H5	0.9500
C4—C5	1.428 (2)
C2—N1—H1	116.8 (15)	C6—C7—H7A	109.5
C6—N1—C2	122.02 (14)	C6—C7—H7B	109.5
C6—N1—H1	120.9 (16)	C6—C7—H7C	109.5
C2—C3—H3	119.5	N1—C6—C7	116.70 (14)
C2—C3—C4	121.06 (16)	N1—C6—C5	119.79 (15)
C4—C3—H3	119.5	C5—C6—C7	123.49 (16)
N1—C2—C3	119.80 (16)	C2—C1—H1A	109.5
N1—C2—C1	116.63 (15)	C2—C1—H1B	109.5
C3—C2—C1	123.57 (16)	C2—C1—H1C	109.5
O1—C4—C3	122.52 (15)	H1A—C1—H1B	109.5
O1—C4—C5	121.34 (16)	H1A—C1—H1C	109.5
C3—C4—C5	116.14 (15)	H1B—C1—H1C	109.5
H7A—C7—H7B	109.5	C4—C5—H5	119.4
H7A—C7—H7C	109.5	C6—C5—C4	121.12 (16)
H7B—C7—H7C	109.5	C6—C5—H5	119.4
O1—C4—C5—C6	−179.53 (17)	C2—C3—C4—C5	−2.6 (3)
N1—C6—C5—C4	1.2 (3)	C4—C3—C2—N1	2.5 (3)
C3—C4—C5—C6	0.7 (3)	C4—C3—C2—C1	−176.66 (16)
C2—N1—C6—C7	177.28 (17)	C7—C6—C5—C4	−177.33 (17)
C2—N1—C6—C5	−1.4 (3)	C6—N1—C2—C3	−0.5 (3)
C2—C3—C4—O1	177.66 (16)	C6—N1—C2—C1	178.74 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.86 (1)	1.96 (1)	2.8174 (17)	173 (2)
N1—H1···O1i	0.87 (1)	1.86 (1)	2.7154 (18)	166 (3)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2O1	0.86(1)	1.96(1)	2.8174(17)	173(2)
N1H1O1i	0.87(1)	1.86(1)	2.7154(18)	166(3)

Symmetry code: (i) .