1-Benzyl-5-ethyl-5-hy-droxy-1H-pyrrol-2(5H)-one.

The title compound, C13H15NO2, was obtained as a by-product in the Grignard reaction of malimide. The dihedral angle between the five-memebred ring (r.m.s. deviation = 0.005 Å) and the benzene ring is 67.20 (14)°. The benzene ring and the ethyl chain lie to the same side of the five-membered ring. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating C(6) chains propagating in [010].

Related literature

For background to the Grignard reaction of malimide, see: Huang (2006 ▶); He et al. (2003 ▶). For related structures, see: Goh et al. (2007 ▶); Ma & Xie (2002 ▶).

Experimental

Crystal data

C13H15NO2

M = 215.27

Monoclinic,

a = 7.0399 (14) Å

b = 7.1795 (14) Å

c = 11.817 (2) Å

β = 102.72 (3)°

V = 582.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.980, T max = 0.983

3363 measured reflections

1947 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.145

S = 1.13

1947 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016887/hb7096sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016887/hb7096Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016887/hb7096Isup3.cml

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

C13H15NO2	F(000) = 230
Mr = 215.27	Dx = 1.227 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.0399 (14) Å	Cell parameters from 2119 reflections
b = 7.1795 (14) Å	θ = 3.0–27.0°
c = 11.817 (2) Å	µ = 0.08 mm−1
β = 102.72 (3)°	T = 173 K
V = 582.6 (2) Å3	Pillar, colourless
Z = 2	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer	1947 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1811 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 16.1903 pixels mm-1	θmax = 27.0°, θmin = 3.0°
phi and ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→9
Tmin = 0.980, Tmax = 0.983	l = −14→15
3363 measured reflections

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) = 0.145	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0893P)2 + 0.0423P] where P = (Fo2 + 2Fc2)/3
1947 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.32 e Å−3

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.2177 (3)	0.6481 (3)	0.96950 (15)	0.0294 (4)
N1	−0.0106 (3)	0.7331 (3)	0.85306 (15)	0.0214 (4)
C1	−0.2478 (4)	0.4825 (5)	0.4747 (2)	0.0383 (7)
H1A	−0.2359	0.4924	0.3981	0.046*
O2	0.2472 (3)	0.9389 (2)	0.83792 (15)	0.0294 (4)
H2A	0.2397	1.0049	0.8934	0.044*
C2	−0.3230 (4)	0.3208 (5)	0.5114 (2)	0.0403 (7)
H2B	−0.36	0.2222	0.4602	0.048*
C3	−0.3426 (4)	0.3079 (5)	0.6254 (2)	0.0352 (6)
H3A	−0.3927	0.2	0.6511	0.042*
C4	0.2774 (4)	0.6967 (4)	0.9869 (2)	0.0291 (6)
H4A	0.4086	0.6937	1.0235	0.035*
C5	−0.1894 (4)	0.6312 (4)	0.5507 (2)	0.0325 (6)
H5A	−0.1362	0.738	0.5255	0.039*
C6	−0.1548 (4)	0.7814 (4)	0.74846 (19)	0.0254 (5)
H6A	−0.1033	0.8808	0.7084	0.03*
H6B	−0.2707	0.8281	0.7706	0.03*
C7	0.2009 (4)	0.7521 (3)	0.8611 (2)	0.0241 (5)
C8	−0.2875 (4)	0.4557 (4)	0.7009 (2)	0.0283 (6)
H8A	−0.3016	0.4459	0.7771	0.034*
C9	−0.0541 (3)	0.6758 (3)	0.95313 (19)	0.0225 (5)
C10	−0.2118 (3)	0.6177 (4)	0.66498 (19)	0.0252 (5)
C11	0.1357 (4)	0.6535 (4)	1.0372 (2)	0.0300 (6)
H11A	0.151	0.6149	1.1138	0.036*
C12	0.2726 (4)	0.6284 (4)	0.7756 (2)	0.0286 (6)
H12A	0.4104	0.652	0.7826	0.034*
H12B	0.2061	0.6643	0.6978	0.034*
C13	0.2442 (4)	0.4196 (4)	0.7893 (2)	0.0335 (6)
H13A	0.2931	0.3535	0.7311	0.05*
H13B	0.1081	0.3932	0.7807	0.05*
H13C	0.3136	0.3806	0.8649	0.05*

	U11	U22	U33	U12	U13	U23
O1	0.0328 (9)	0.0290 (11)	0.0303 (9)	−0.0023 (8)	0.0153 (7)	−0.0011 (8)
N1	0.0209 (9)	0.0227 (10)	0.0203 (8)	0.0000 (8)	0.0035 (7)	−0.0002 (8)
C1	0.0360 (14)	0.053 (2)	0.0254 (12)	0.0033 (15)	0.0061 (10)	−0.0087 (13)
O2	0.0358 (10)	0.0214 (10)	0.0325 (9)	−0.0076 (8)	0.0104 (7)	0.0009 (7)
C2	0.0317 (14)	0.052 (2)	0.0370 (14)	−0.0020 (14)	0.0067 (11)	−0.0215 (14)
C3	0.0295 (14)	0.0360 (16)	0.0398 (14)	−0.0060 (12)	0.0068 (11)	−0.0067 (12)
C4	0.0289 (12)	0.0263 (14)	0.0283 (11)	−0.0024 (11)	−0.0020 (9)	0.0022 (10)
C5	0.0311 (13)	0.0398 (16)	0.0260 (12)	0.0042 (12)	0.0049 (10)	0.0011 (12)
C6	0.0249 (12)	0.0254 (13)	0.0242 (11)	0.0054 (10)	0.0017 (9)	0.0016 (10)
C7	0.0224 (11)	0.0218 (13)	0.0274 (11)	−0.0005 (10)	0.0039 (8)	0.0017 (10)
C8	0.0237 (11)	0.0339 (16)	0.0268 (11)	0.0028 (11)	0.0047 (8)	−0.0044 (11)
C9	0.0300 (12)	0.0150 (11)	0.0230 (10)	−0.0016 (10)	0.0069 (8)	−0.0021 (9)
C10	0.0196 (10)	0.0320 (14)	0.0222 (10)	0.0058 (11)	0.0004 (8)	−0.0033 (10)
C11	0.0363 (13)	0.0278 (14)	0.0225 (11)	−0.0053 (12)	−0.0008 (9)	0.0013 (10)
C12	0.0244 (12)	0.0275 (14)	0.0362 (13)	0.0000 (10)	0.0118 (9)	0.0008 (11)
C13	0.0310 (14)	0.0260 (13)	0.0449 (14)	0.0059 (12)	0.0114 (11)	−0.0022 (12)

O1—C9	1.225 (3)	C5—C10	1.397 (3)
N1—C9	1.349 (3)	C5—H5A	0.93
N1—C6	1.458 (3)	C6—C10	1.530 (3)
N1—C7	1.477 (3)	C6—H6A	0.97
C1—C2	1.385 (5)	C6—H6B	0.97
C1—C5	1.397 (4)	C7—C12	1.513 (4)
C1—H1A	0.93	C8—C10	1.384 (4)
O2—C7	1.421 (3)	C8—H8A	0.93
O2—H2A	0.82	C9—C11	1.488 (3)
C2—C3	1.387 (4)	C11—H11A	0.93
C2—H2B	0.93	C12—C13	1.526 (4)
C3—C8	1.386 (4)	C12—H12A	0.97
C3—H3A	0.93	C12—H12B	0.97
C4—C11	1.306 (4)	C13—H13A	0.96
C4—C7	1.518 (3)	C13—H13B	0.96
C4—H4A	0.93	C13—H13C	0.96
C9—N1—C6	124.4 (2)	O2—C7—C4	112.9 (2)
C9—N1—C7	113.05 (18)	N1—C7—C4	100.05 (19)
C6—N1—C7	122.47 (19)	C12—C7—C4	113.7 (2)
C2—C1—C5	121.2 (2)	C10—C8—C3	121.2 (2)
C2—C1—H1A	119.4	C10—C8—H8A	119.4
C5—C1—H1A	119.4	C3—C8—H8A	119.4
C7—O2—H2A	109.5	O1—C9—N1	126.2 (2)
C1—C2—C3	119.1 (3)	O1—C9—C11	127.9 (2)
C1—C2—H2B	120.4	N1—C9—C11	105.9 (2)
C3—C2—H2B	120.4	C8—C10—C5	119.2 (2)
C8—C3—C2	120.0 (3)	C8—C10—C6	120.7 (2)
C8—C3—H3A	120	C5—C10—C6	120.0 (2)
C2—C3—H3A	120	C4—C11—C9	109.5 (2)
C11—C4—C7	111.5 (2)	C4—C11—H11A	125.3
C11—C4—H4A	124.3	C9—C11—H11A	125.3
C7—C4—H4A	124.3	C7—C12—C13	115.8 (2)
C10—C5—C1	119.2 (3)	C7—C12—H12A	108.3
C10—C5—H5A	120.4	C13—C12—H12A	108.3
C1—C5—H5A	120.4	C7—C12—H12B	108.3
N1—C6—C10	113.5 (2)	C13—C12—H12B	108.3
N1—C6—H6A	108.9	H12A—C12—H12B	107.4
C10—C6—H6A	108.9	C12—C13—H13A	109.5
N1—C6—H6B	108.9	C12—C13—H13B	109.5
C10—C6—H6B	108.9	H13A—C13—H13B	109.5
H6A—C6—H6B	107.7	C12—C13—H13C	109.5
O2—C7—N1	110.21 (19)	H13A—C13—H13C	109.5
O2—C7—C12	107.48 (19)	H13B—C13—H13C	109.5
N1—C7—C12	112.5 (2)
C5—C1—C2—C3	0.8 (4)	C7—N1—C9—O1	−179.5 (2)
C1—C2—C3—C8	0.1 (4)	C6—N1—C9—C11	−176.7 (2)
C2—C1—C5—C10	−1.5 (4)	C7—N1—C9—C11	0.3 (3)
C9—N1—C6—C10	−92.1 (3)	C3—C8—C10—C5	−0.5 (4)
C7—N1—C6—C10	91.2 (3)	C3—C8—C10—C6	178.9 (2)
C9—N1—C7—O2	−119.7 (2)	C1—C5—C10—C8	1.4 (4)
C6—N1—C7—O2	57.4 (3)	C1—C5—C10—C6	−178.0 (2)
C9—N1—C7—C12	120.4 (2)	N1—C6—C10—C8	57.8 (3)
C6—N1—C7—C12	−62.5 (3)	N1—C6—C10—C5	−122.8 (2)
C9—N1—C7—C4	−0.6 (3)	C7—C4—C11—C9	−0.6 (3)
C6—N1—C7—C4	176.5 (2)	O1—C9—C11—C4	180.0 (3)
C11—C4—C7—O2	117.8 (3)	N1—C9—C11—C4	0.2 (3)
C11—C4—C7—N1	0.7 (3)	O2—C7—C12—C13	177.5 (2)
C11—C4—C7—C12	−119.4 (3)	N1—C7—C12—C13	−61.0 (3)
C2—C3—C8—C10	−0.2 (4)	C4—C7—C12—C13	51.8 (3)
C6—N1—C9—O1	3.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.82	1.95	2.772 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1i	0.82	1.95	2.772 (3)	176

Symmetry code: (i) .