(2RS)-3-Hydr-oxy-2-methyl-2-(2-pyrid-yl)imidazolidine-4-one.

The title structure, C(9)H(11)N(3)O(2), is a racemate. The chiral centre is situated at the N-C-N C atom of the imidazolidine ring. The inter-planar angle between the mean planes of the pyridine and imidazolidine rings is 89.41 (5)°. The methyl group is in a trans position with respect to the pyridine N atom. In the crystal, the mol-ecules are arranged in zigzag layers parallel to the b axis. The mol-ecules within the layers are inter-connected by strong O-H⋯N and weak N-H⋯O hydrogen bonds; the former take place between OH groups and amine N atoms and the latter between the amine N atom and the carbonyl O atom. In addition, C-H⋯O inter-actions are also present.

Related literature

For background to hydroxamic acids in biological and coord­ination chemistry, see: Miller (1989 ▶); Lipczynska-Kochany (1991 ▶); Kurzak et al. (1992 ▶); Whittaker et al. (1999 ▶). For reactions of α-amino n class="Chemical">hydroxamic acids with aldehydes and ketones resulting in 3-hydroxy­imidazolidin-4-one derivatives, see: Vystorop et al. (2002 ▶, 2003 ▶); Marson & Pucci (2004 ▶). For related structures, see: Krämer & Fritsky (2000 ▶); Świątek-Kozłowska et al. (2000 ▶); Krämer et al. (2002 ▶); Kovbasyuk et al. (2004 ▶). For the synthesis, see: Cunningham et al. (1949 ▶). For hydrogen bonds, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C9H11N3O2

M = 193.21

Monoclinic,

a = 8.207 (2) Å

b = 10.604 (2) Å

c = 10.642 (2) Å

β = 106.43 (3)°

V = 888.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.25 × 0.17 × 0.12 mm

Data collection

Kuma KM-4-CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED, Oxford Diffraction, 2006 ▶) T min = 0.976, T max = 0.986

6025 measured reflections

2048 independent reflections

1772 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.092

S = 1.12

2048 reflections

137 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030840/fb2163sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030840/fb2163Isup2.hkl

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

C9H11N3O2	F(000) = 408
Mr = 193.21	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 505 reflections
a = 8.207 (2) Å	θ = 4.5–27.0°
b = 10.604 (2) Å	µ = 0.11 mm−1
c = 10.642 (2) Å	T = 100 K
β = 106.43 (3)°	Block, colourless
V = 888.3 (3) Å3	0.25 × 0.17 × 0.12 mm
Z = 4

Kuma KM-4-CCD diffractometer	2048 independent reflections
Radiation source: fine-focus sealed tube	1772 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 28.4°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis RED, Oxford Diffraction, 2006)	h = −10→10
Tmin = 0.976, Tmax = 0.986	k = −12→14
6025 measured reflections	l = −10→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.2114P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2048 reflections	Δρmax = 0.31 e Å−3
137 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
35 constraints	Extinction coefficient: 0.011 (3)
Primary atom site location: structure-invariant direct methods

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
O1	0.16520 (11)	0.16310 (8)	0.36523 (9)	0.0161 (2)
O2	0.40231 (11)	0.01414 (8)	0.28974 (9)	0.0197 (2)
N1	0.33317 (13)	0.31162 (10)	0.12474 (10)	0.0143 (2)
N2	0.02391 (13)	0.16898 (10)	0.05476 (10)	0.0162 (2)
N3	0.27351 (13)	0.20590 (10)	0.29470 (10)	0.0135 (2)
C1	0.21832 (17)	0.43456 (12)	0.27885 (13)	0.0175 (3)
H1A	0.1455	0.4293	0.3351	0.026*
H1B	0.1815	0.5026	0.2179	0.026*
H1C	0.3330	0.4496	0.3307	0.026*
C2	0.21024 (15)	0.31194 (11)	0.20447 (11)	0.0137 (3)
C3	0.03258 (15)	0.27995 (11)	0.11645 (11)	0.0137 (3)
C4	0.36622 (15)	0.12145 (12)	0.24864 (12)	0.0147 (3)
C5	0.41829 (16)	0.18664 (12)	0.14047 (12)	0.0167 (3)
H5A	0.5407	0.1966	0.1638	0.020*
H5B	0.3818	0.1385	0.0598	0.020*
C6	−0.10579 (17)	0.36021 (12)	0.09906 (13)	0.0184 (3)
H6	−0.0958	0.4360	0.1446	0.022*
C7	−0.25965 (17)	0.32455 (13)	0.01199 (13)	0.0206 (3)
H7	−0.3546	0.3762	−0.0018	0.025*
C8	−0.26922 (16)	0.21144 (13)	−0.05353 (13)	0.0196 (3)
H8	−0.3702	0.1859	−0.1130	0.023*
C9	−0.12508 (16)	0.13664 (12)	−0.02886 (12)	0.0177 (3)
H9	−0.1323	0.0601	−0.0727	0.021*
H1O	0.229 (3)	0.1711 (18)	0.454 (2)	0.049 (6)*
H1N	0.409 (2)	0.3703 (16)	0.1556 (15)	0.023 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0174 (5)	0.0199 (5)	0.0126 (4)	−0.0039 (3)	0.0067 (4)	0.0010 (3)
O2	0.0196 (5)	0.0154 (5)	0.0233 (5)	0.0026 (3)	0.0050 (4)	0.0021 (4)
N1	0.0146 (5)	0.0152 (5)	0.0135 (5)	−0.0028 (4)	0.0049 (4)	−0.0007 (4)
N2	0.0169 (5)	0.0145 (5)	0.0166 (5)	−0.0009 (4)	0.0040 (4)	−0.0016 (4)
N3	0.0147 (5)	0.0148 (5)	0.0117 (5)	−0.0010 (4)	0.0052 (4)	0.0016 (4)
C1	0.0208 (7)	0.0143 (6)	0.0172 (6)	−0.0012 (5)	0.0052 (5)	−0.0020 (5)
C2	0.0165 (6)	0.0132 (6)	0.0118 (6)	0.0003 (4)	0.0046 (5)	0.0010 (4)
C3	0.0162 (6)	0.0139 (6)	0.0117 (6)	−0.0012 (4)	0.0050 (5)	0.0011 (4)
C4	0.0111 (6)	0.0170 (6)	0.0139 (6)	−0.0022 (4)	−0.0001 (4)	−0.0033 (5)
C5	0.0161 (6)	0.0186 (6)	0.0160 (6)	0.0012 (5)	0.0057 (5)	−0.0010 (5)
C6	0.0211 (7)	0.0155 (6)	0.0187 (6)	0.0025 (5)	0.0060 (5)	−0.0019 (5)
C7	0.0173 (7)	0.0221 (7)	0.0216 (7)	0.0063 (5)	0.0042 (5)	0.0027 (5)
C8	0.0156 (6)	0.0236 (7)	0.0171 (6)	−0.0009 (5)	0.0008 (5)	0.0017 (5)
C9	0.0194 (7)	0.0161 (6)	0.0167 (6)	−0.0022 (5)	0.0036 (5)	−0.0029 (5)

O1—N3	1.3917 (13)	C1—H1C	0.9600
O1—H1O	0.95 (2)	C2—C3	1.5316 (18)
O2—C4	1.2250 (16)	C3—C6	1.3891 (17)
N1—C5	1.4854 (16)	C4—C5	1.5047 (17)
N1—C2	1.4907 (16)	C5—H5A	0.9700
N1—H1N	0.874 (17)	C5—H5B	0.9700
N2—C9	1.3376 (17)	C6—C7	1.3908 (19)
N2—C3	1.3395 (16)	C6—H6	0.9300
N3—C4	1.3536 (16)	C7—C8	1.3783 (19)
N3—C2	1.4744 (16)	C7—H7	0.9300
C1—C2	1.5139 (17)	C8—C9	1.3863 (19)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—H9	0.9300
N3—O1—H1O	104.8 (12)	C6—C3—C2	123.14 (11)
C5—N1—C2	108.08 (9)	O2—C4—N3	126.10 (12)
C5—N1—H1N	109.4 (11)	O2—C4—C5	127.42 (11)
C2—N1—H1N	107.8 (10)	N3—C4—C5	106.47 (11)
C9—N2—C3	117.59 (11)	N1—C5—C4	105.65 (10)
C4—N3—O1	119.32 (10)	N1—C5—H5A	110.6
C4—N3—C2	113.53 (10)	C4—C5—H5A	110.6
O1—N3—C2	116.04 (9)	N1—C5—H5B	110.6
C2—C1—H1A	109.5	C4—C5—H5B	110.6
C2—C1—H1B	109.5	H5A—C5—H5B	108.7
H1A—C1—H1B	109.5	C3—C6—C7	118.43 (12)
C2—C1—H1C	109.5	C3—C6—H6	120.8
H1A—C1—H1C	109.5	C7—C6—H6	120.8
H1B—C1—H1C	109.5	C8—C7—C6	119.00 (12)
N3—C2—N1	101.45 (9)	C8—C7—H7	120.5
N3—C2—C1	111.05 (10)	C6—C7—H7	120.5
N1—C2—C1	111.28 (10)	C7—C8—C9	118.60 (12)
N3—C2—C3	109.17 (10)	C7—C8—H8	120.7
N1—C2—C3	109.38 (9)	C9—C8—H8	120.7
C1—C2—C3	113.79 (10)	N2—C9—C8	123.35 (12)
N2—C3—C6	123.02 (12)	N2—C9—H9	118.3
N2—C3—C2	113.82 (10)	C8—C9—H9	118.3
C4—N3—C2—N1	−23.00 (12)	N1—C2—C3—C6	−120.73 (13)
O1—N3—C2—N1	−166.82 (9)	C1—C2—C3—C6	4.41 (17)
C4—N3—C2—C1	−141.35 (11)	O1—N3—C4—O2	−21.10 (17)
O1—N3—C2—C1	74.84 (13)	C2—N3—C4—O2	−163.63 (11)
C4—N3—C2—C3	92.40 (12)	O1—N3—C4—C5	160.17 (9)
O1—N3—C2—C3	−51.42 (13)	C2—N3—C4—C5	17.65 (13)
C5—N1—C2—N3	18.56 (12)	C2—N1—C5—C4	−9.58 (12)
C5—N1—C2—C1	136.75 (10)	O2—C4—C5—N1	176.85 (11)
C5—N1—C2—C3	−96.68 (11)	N3—C4—C5—N1	−4.45 (13)
C9—N2—C3—C6	1.26 (18)	N2—C3—C6—C7	−1.06 (19)
C9—N2—C3—C2	−176.93 (11)	C2—C3—C6—C7	176.96 (11)
N3—C2—C3—N2	−52.74 (13)	C3—C6—C7—C8	0.01 (19)
N1—C2—C3—N2	57.46 (13)	C6—C7—C8—C9	0.7 (2)
C1—C2—C3—N2	−177.41 (10)	C3—N2—C9—C8	−0.43 (19)
N3—C2—C3—C6	129.08 (12)	C7—C8—C9—N2	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1i	0.95 (2)	1.78 (2)	2.7287 (16)	175.5 (18)
N1—H1N···O2ii	0.874 (17)	2.135 (18)	3.0058 (15)	173.7 (15)
C6—H6···O1iii	0.93	2.47	3.2867 (17)	147
C7—H7···O2iii	0.93	2.81	3.3559 (17)	119
C8—H8···O2iv	0.93	2.80	3.4177 (17)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1i	0.95 (2)	1.78 (2)	2.7287 (16)	175.5 (18)
N1—H1N⋯O2ii	0.874 (17)	2.135 (18)	3.0058 (15)	173.7 (15)
C6—H6⋯O1iii	0.93	2.47	3.2867 (17)	147
C7—H7⋯O2iii	0.93	2.81	3.3559 (17)	119
C8—H8⋯O2iv	0.93	2.80	3.4177 (17)	125

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .