(Z)-3-[(4-Eth-oxy-phen-yl)(hy-droxy)methyl-idene]-1-isopropyl-pyrrolidine-2,4-dione.

In the title compound, C(16)H(19)NO(4), a potent new herbicide, the dihedral angle between the benzene and pyrrolidine rings is 11.09 (8)°. Intra-molecular O-H⋯O and C-H⋯O hydrogen bonds are observed.

Related literature

For the anti­biotic activity of 3-acyl­pyrrolidine-2,4-dione compounds, see: van der Baan et al. (1978 ▶); Holzapfel et al. (1970 ▶); Mackellar et al. (1971 ▶); Rinehart et al. (1963 ▶); Sticking (1959 ▶); Wu et al. (2002 ▶). For a related structure, see: Ellis & Spek (2001 ▶). For the synthesis, see: Matsuo et al. (1980 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H19NO4

M = 289.32

Monoclinic,

a = 11.3390 (15) Å

b = 5.3830 (8) Å

c = 12.0490 (18) Å

β = 91.581 (7)°

V = 735.16 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.42 × 0.26 × 0.10 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ▶) T min = 0.962, T max = 0.991

9386 measured reflections

1933 independent reflections

1668 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.079

S = 1.03

1933 reflections

193 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrystalClear (Rigaku, 2009 ▶); 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: CrystalStructure (Rigaku, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046465/is2629sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046465/is2629Isup2.hkl

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

C16H19NO4	F(000) = 308
Mr = 289.32	Dx = 1.307 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2yb	Cell parameters from 2865 reflections
a = 11.3390 (15) Å	θ = 1.8–27.9°
b = 5.3830 (8) Å	µ = 0.09 mm−1
c = 12.0490 (18) Å	T = 113 K
β = 91.581 (7)°	Prism, colorless
V = 735.16 (18) Å3	0.42 × 0.26 × 0.10 mm
Z = 2

Rigaku Saturn724 CCD diffractometer	1933 independent reflections
Radiation source: rotating anode	1668 reflections with I > 2σ(I)
multilayer	Rint = 0.040
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 1.8°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −7→7
Tmin = 0.962, Tmax = 0.991	l = −15→15
9386 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3
1933 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

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	0.70417 (9)	0.6075 (2)	0.35972 (9)	0.0257 (3)
H1A	0.7435	0.6020	0.3017	0.039*
O2	0.84775 (9)	0.4899 (2)	0.21845 (9)	0.0251 (3)
O3	0.89526 (9)	−0.0316 (2)	0.53336 (9)	0.0251 (3)
O4	0.48151 (10)	0.4135 (3)	0.82015 (9)	0.0299 (3)
N1	0.96813 (11)	0.1603 (3)	0.26539 (10)	0.0203 (3)
C1	0.74116 (13)	0.4313 (3)	0.42897 (13)	0.0193 (3)
C2	0.83157 (13)	0.2766 (3)	0.39424 (13)	0.0186 (3)
C3	0.88176 (13)	0.3211 (3)	0.28521 (13)	0.0192 (3)
C4	0.99039 (13)	−0.0049 (3)	0.35867 (12)	0.0204 (3)
H4A	1.0717	0.0165	0.3892	0.024*
H4B	0.9791	−0.1805	0.3364	0.024*
C5	0.89965 (13)	0.0726 (3)	0.44344 (13)	0.0192 (4)
C6	0.67596 (12)	0.4261 (3)	0.53246 (13)	0.0188 (3)
C7	0.59784 (13)	0.6206 (3)	0.55394 (13)	0.0220 (4)
H7	0.5904	0.7537	0.5024	0.026*
C8	0.53130 (13)	0.6236 (3)	0.64833 (13)	0.0233 (4)
H8	0.4786	0.7570	0.6612	0.028*
C9	0.54203 (13)	0.4304 (4)	0.72421 (13)	0.0227 (4)
C10	0.61937 (14)	0.2358 (3)	0.70400 (14)	0.0248 (4)
H10	0.6266	0.1029	0.7556	0.030*
C11	0.68552 (14)	0.2340 (3)	0.60987 (14)	0.0236 (4)
H11	0.7383	0.1004	0.5975	0.028*
C12	0.39293 (16)	0.5968 (4)	0.83947 (16)	0.0361 (5)
H12A	0.3344	0.6001	0.7769	0.043*
H12B	0.4292	0.7635	0.8466	0.043*
C13	0.3340 (2)	0.5264 (5)	0.94565 (16)	0.0554 (7)
H13A	0.2992	0.3605	0.9377	0.067*
H13B	0.2719	0.6472	0.9612	0.067*
H13C	0.3926	0.5258	1.0070	0.067*
C14	1.04354 (13)	0.1741 (3)	0.16876 (13)	0.0222 (4)
H14	1.0084	0.2990	0.1160	0.027*
C15	1.16687 (15)	0.2627 (5)	0.20292 (15)	0.0356 (5)
H15A	1.1614	0.4220	0.2418	0.043*
H15B	1.2141	0.2834	0.1366	0.043*
H15C	1.2045	0.1397	0.2523	0.043*
C16	1.0475 (2)	−0.0729 (5)	0.10959 (16)	0.0481 (6)
H16A	1.0895	−0.1942	0.1567	0.058*
H16B	1.0888	−0.0536	0.0397	0.058*
H16C	0.9669	−0.1313	0.0939	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0261 (6)	0.0265 (7)	0.0247 (6)	0.0059 (5)	0.0053 (5)	0.0076 (6)
O2	0.0245 (6)	0.0277 (7)	0.0231 (6)	0.0011 (5)	0.0015 (4)	0.0074 (6)
O3	0.0269 (6)	0.0281 (7)	0.0206 (6)	0.0076 (5)	0.0045 (4)	0.0060 (6)
O4	0.0266 (6)	0.0393 (8)	0.0242 (6)	0.0102 (6)	0.0078 (5)	0.0036 (6)
N1	0.0208 (6)	0.0248 (8)	0.0155 (6)	0.0013 (6)	0.0028 (5)	0.0015 (6)
C1	0.0176 (7)	0.0179 (9)	0.0223 (8)	−0.0034 (6)	−0.0023 (6)	0.0004 (7)
C2	0.0179 (7)	0.0206 (9)	0.0174 (8)	−0.0034 (6)	0.0008 (6)	0.0015 (7)
C3	0.0180 (7)	0.0205 (9)	0.0191 (8)	−0.0042 (7)	−0.0010 (6)	0.0007 (7)
C4	0.0228 (7)	0.0208 (9)	0.0176 (7)	0.0019 (7)	0.0028 (6)	0.0019 (7)
C5	0.0194 (7)	0.0186 (9)	0.0196 (8)	−0.0019 (6)	0.0002 (6)	−0.0022 (6)
C6	0.0154 (7)	0.0198 (8)	0.0213 (7)	−0.0010 (7)	0.0008 (6)	−0.0005 (7)
C7	0.0218 (7)	0.0205 (9)	0.0235 (8)	0.0005 (7)	−0.0006 (6)	0.0019 (8)
C8	0.0209 (8)	0.0234 (9)	0.0256 (9)	0.0047 (7)	0.0008 (6)	−0.0038 (8)
C9	0.0170 (7)	0.0294 (9)	0.0219 (8)	−0.0005 (7)	0.0028 (6)	−0.0007 (8)
C10	0.0247 (8)	0.0241 (10)	0.0258 (9)	0.0038 (7)	0.0043 (7)	0.0048 (8)
C11	0.0200 (8)	0.0233 (9)	0.0277 (9)	0.0032 (7)	0.0044 (7)	0.0018 (8)
C12	0.0312 (9)	0.0451 (12)	0.0326 (10)	0.0143 (9)	0.0100 (8)	−0.0009 (10)
C13	0.0514 (13)	0.0781 (19)	0.0381 (12)	0.0272 (13)	0.0241 (10)	0.0097 (13)
C14	0.0225 (8)	0.0282 (10)	0.0162 (8)	−0.0014 (7)	0.0039 (6)	0.0007 (7)
C15	0.0266 (9)	0.0562 (14)	0.0244 (9)	−0.0101 (9)	0.0047 (7)	−0.0001 (10)
C16	0.0606 (14)	0.0485 (14)	0.0366 (11)	−0.0181 (12)	0.0245 (10)	−0.0199 (11)

O1—C1	1.324 (2)	C8—H8	0.9500
O1—H1A	0.8400	C9—C10	1.392 (2)
O2—C3	1.2665 (19)	C10—C11	1.377 (2)
O3—C5	1.2222 (19)	C10—H10	0.9500
O4—C9	1.3635 (18)	C11—H11	0.9500
O4—C12	1.432 (2)	C12—C13	1.508 (3)
N1—C3	1.334 (2)	C12—H12A	0.9900
N1—C4	1.450 (2)	C12—H12B	0.9900
N1—C14	1.4654 (18)	C13—H13A	0.9800
C1—C2	1.394 (2)	C13—H13B	0.9800
C1—C6	1.467 (2)	C13—H13C	0.9800
C2—C5	1.459 (2)	C14—C16	1.510 (3)
C2—C3	1.466 (2)	C14—C15	1.523 (2)
C4—C5	1.528 (2)	C14—H14	1.0000
C4—H4A	0.9900	C15—H15A	0.9800
C4—H4B	0.9900	C15—H15B	0.9800
C6—C11	1.395 (2)	C15—H15C	0.9800
C6—C7	1.400 (2)	C16—H16A	0.9800
C7—C8	1.382 (2)	C16—H16B	0.9800
C7—H7	0.9500	C16—H16C	0.9800
C8—C9	1.388 (2)
C1—O1—H1A	109.5	C11—C10—H10	119.7
C9—O4—C12	117.63 (14)	C9—C10—H10	119.7
C3—N1—C4	111.86 (12)	C10—C11—C6	120.77 (16)
C3—N1—C14	123.82 (14)	C10—C11—H11	119.6
C4—N1—C14	123.67 (12)	C6—C11—H11	119.6
O1—C1—C2	117.49 (14)	O4—C12—C13	107.10 (18)
O1—C1—C6	113.02 (13)	O4—C12—H12A	110.3
C2—C1—C6	129.47 (14)	C13—C12—H12A	110.3
C1—C2—C5	135.48 (14)	O4—C12—H12B	110.3
C1—C2—C3	118.59 (14)	C13—C12—H12B	110.3
C5—C2—C3	105.84 (13)	H12A—C12—H12B	108.5
O2—C3—N1	124.35 (14)	C12—C13—H13A	109.5
O2—C3—C2	124.57 (14)	C12—C13—H13B	109.5
N1—C3—C2	111.08 (13)	H13A—C13—H13B	109.5
N1—C4—C5	104.16 (13)	C12—C13—H13C	109.5
N1—C4—H4A	110.9	H13A—C13—H13C	109.5
C5—C4—H4A	110.9	H13B—C13—H13C	109.5
N1—C4—H4B	110.9	N1—C14—C16	110.85 (14)
C5—C4—H4B	110.9	N1—C14—C15	110.65 (12)
H4A—C4—H4B	108.9	C16—C14—C15	111.34 (16)
O3—C5—C2	132.20 (15)	N1—C14—H14	108.0
O3—C5—C4	120.79 (15)	C16—C14—H14	108.0
C2—C5—C4	107.01 (13)	C15—C14—H14	108.0
C11—C6—C7	117.94 (15)	C14—C15—H15A	109.5
C11—C6—C1	123.43 (14)	C14—C15—H15B	109.5
C7—C6—C1	118.61 (14)	H15A—C15—H15B	109.5
C8—C7—C6	121.55 (16)	C14—C15—H15C	109.5
C8—C7—H7	119.2	H15A—C15—H15C	109.5
C6—C7—H7	119.2	H15B—C15—H15C	109.5
C7—C8—C9	119.57 (16)	C14—C16—H16A	109.5
C7—C8—H8	120.2	C14—C16—H16B	109.5
C9—C8—H8	120.2	H16A—C16—H16B	109.5
O4—C9—C8	124.84 (15)	C14—C16—H16C	109.5
O4—C9—C10	115.63 (15)	H16A—C16—H16C	109.5
C8—C9—C10	119.53 (15)	H16B—C16—H16C	109.5
C11—C10—C9	120.63 (16)
O1—C1—C2—C5	177.26 (17)	C2—C1—C6—C11	−9.0 (2)
C6—C1—C2—C5	−4.6 (3)	O1—C1—C6—C7	−9.19 (19)
O1—C1—C2—C3	1.3 (2)	C2—C1—C6—C7	172.57 (16)
C6—C1—C2—C3	179.52 (15)	C11—C6—C7—C8	−0.3 (2)
C4—N1—C3—O2	177.77 (14)	C1—C6—C7—C8	178.19 (14)
C14—N1—C3—O2	6.7 (2)	C6—C7—C8—C9	0.3 (2)
C4—N1—C3—C2	−2.23 (18)	C12—O4—C9—C8	5.8 (2)
C14—N1—C3—C2	−173.26 (13)	C12—O4—C9—C10	−174.26 (16)
C1—C2—C3—O2	−1.0 (2)	C7—C8—C9—O4	179.75 (15)
C5—C2—C3—O2	−178.00 (14)	C7—C8—C9—C10	−0.2 (2)
C1—C2—C3—N1	179.02 (14)	O4—C9—C10—C11	−179.68 (14)
C5—C2—C3—N1	2.00 (17)	C8—C9—C10—C11	0.3 (2)
C3—N1—C4—C5	1.48 (17)	C9—C10—C11—C6	−0.4 (2)
C14—N1—C4—C5	172.53 (14)	C7—C6—C11—C10	0.4 (2)
C1—C2—C5—O3	2.1 (3)	C1—C6—C11—C10	−178.04 (14)
C3—C2—C5—O3	178.34 (17)	C9—O4—C12—C13	176.02 (16)
C1—C2—C5—C4	−177.28 (17)	C3—N1—C14—C16	−129.11 (18)
C3—C2—C5—C4	−1.00 (16)	C4—N1—C14—C16	60.9 (2)
N1—C4—C5—O3	−179.62 (14)	C3—N1—C14—C15	106.86 (18)
N1—C4—C5—C2	−0.19 (16)	C4—N1—C14—C15	−63.1 (2)
O1—C1—C6—C11	169.26 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.84	1.68	2.4701 (16)	155
C11—H11···O3	0.95	2.08	2.945 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.84	1.68	2.4701 (16)	155
C11—H11⋯O3	0.95	2.08	2.945 (2)	150