3-[(Hydr-oxy)(4-isoprop-oxy-2-methoxy-phen-yl)methyl-ene]-1-isopropyl-pyrrol-idine-2,4-dione.

The title compound, C(18)H(23)NO(5), a potential herbicide, has an enol group that is intra-molecularly hydrogen bonded to a keto O atom. The dihedral angle between the six-membered ring formed by the enol group and the aromatic benzene ring is 53.35 (6)°.

Related literature

For structural and herbicidal literature on this class of compounds, see: Ellis & Spek (2001 ▶); Holzapfel et al. (1970 ▶); Rinehart et al. (1971 ▶, 1963 ▶); Matsuo et al. (1980 ▶); van Rooyen (1992 ▶); Stickings (1959 ▶); Van Der Baan et al. (1978 ▶); Xu (2005 ▶); Zhu, Hu & Yang (2004 ▶); Zhu, Song, Li et al. (2004 ▶); Zhu, Song, Yao et al. (2004 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H23NO5

M = 333.37

Monoclinic,

a = 14.694 (2) Å

b = 12.249 (2) Å

c = 20.308 (3) Å

β = 103.864 (3)°

V = 3548.5 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

9820 measured reflections

3622 independent reflections

2199 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.04

3622 reflections

223 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807060588/ng2379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060588/ng2379Isup2.hkl

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

C18H23NO5	Z = 8
Mr = 333.37	F000 = 1424
Monoclinic, C2/c	Dx = 1.248 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 14.694 (2) Å	θ = 2.6–23.1º
b = 12.249 (2) Å	µ = 0.09 mm−1
c = 20.308 (3) Å	T = 294 (2) K
β = 103.864 (3)º	Prism, colourless
V = 3548.5 (10) Å3	0.26 × 0.24 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2199 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Monochromator: graphite	θmax = 26.4º
T = 294(2) K	θmin = 2.1º
φ and ω scans	h = −18→8
Absorption correction: none	k = −15→15
9820 measured reflections	l = −24→25
3622 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.066P)2 + 0.41P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3622 reflections	Δρmax = 0.19 e Å−3
223 parameters	Δρmin = −0.20 e Å−3
12 restraints	Extinction correction: none
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	0.08411 (12)	0.33480 (12)	0.57101 (7)	0.0604 (4)
O2	0.17331 (10)	0.25752 (11)	0.36755 (7)	0.0532 (4)
O3	0.10441 (13)	0.05253 (13)	0.31692 (7)	0.0695 (5)
H3	0.1164	0.0047	0.2921	0.104*
O4	0.18049 (11)	−0.11472 (12)	0.27727 (7)	0.0566 (4)
O5	0.28614 (11)	−0.06071 (13)	0.51329 (7)	0.0625 (5)
N1	0.28941 (12)	−0.19911 (14)	0.36200 (8)	0.0452 (4)
C1	−0.0325 (2)	0.2778 (3)	0.63023 (14)	0.0851 (9)
H1A	−0.0707	0.3396	0.6124	0.128*
H1B	−0.0417	0.2597	0.6742	0.128*
H1C	−0.0499	0.2167	0.6003	0.128*
C2	0.06866 (16)	0.30512 (19)	0.63625 (11)	0.0552 (6)
H2	0.1076	0.2419	0.6542	0.066*
C3	0.1002 (2)	0.4022 (2)	0.68087 (13)	0.0837 (9)
H3A	0.1648	0.4172	0.6826	0.126*
H3B	0.0931	0.3871	0.7258	0.126*
H3C	0.0628	0.4645	0.6628	0.126*
C4	0.09829 (14)	0.25628 (16)	0.52731 (10)	0.0441 (5)
C5	0.12539 (13)	0.29580 (16)	0.47092 (10)	0.0427 (5)
H5	0.1314	0.3706	0.4655	0.051*
C6	0.14353 (13)	0.22495 (16)	0.42277 (9)	0.0400 (5)
C7	0.13459 (14)	0.11166 (15)	0.43064 (10)	0.0416 (5)
C8	0.10772 (15)	0.07488 (17)	0.48725 (11)	0.0509 (5)
H8	0.1023	0.0001	0.4931	0.061*
C9	0.08852 (16)	0.14464 (17)	0.53562 (11)	0.0531 (6)
H9	0.0695	0.1175	0.5729	0.064*
C10	0.18157 (18)	0.37182 (18)	0.35704 (11)	0.0608 (6)
H10A	0.1205	0.4048	0.3477	0.091*
H10B	0.2091	0.3835	0.3193	0.091*
H10C	0.2206	0.4041	0.3970	0.091*
C11	0.15126 (14)	0.03387 (16)	0.37983 (10)	0.0442 (5)
C12	0.20977 (14)	−0.05513 (15)	0.39318 (9)	0.0391 (5)
C13	0.22342 (14)	−0.12462 (15)	0.33812 (10)	0.0409 (5)
C14	0.32846 (17)	−0.18606 (18)	0.43457 (10)	0.0555 (6)
H14A	0.3948	−0.1692	0.4439	0.067*
H14B	0.3199	−0.2520	0.4589	0.067*
C15	0.27400 (14)	−0.09173 (16)	0.45477 (10)	0.0449 (5)
C16	0.32451 (15)	−0.27819 (16)	0.31986 (10)	0.0477 (5)
H16	0.2810	−0.2783	0.2750	0.057*
C17	0.41877 (18)	−0.2440 (2)	0.31078 (13)	0.0768 (8)
H17A	0.4149	−0.1711	0.2930	0.115*
H17B	0.4381	−0.2930	0.2798	0.115*
H17C	0.4636	−0.2461	0.3538	0.115*
C18	0.3244 (3)	−0.3906 (2)	0.34875 (15)	0.1083 (12)
H18A	0.3691	−0.3942	0.3917	0.162*
H18B	0.3408	−0.4427	0.3182	0.162*
H18C	0.2630	−0.4071	0.3548	0.162*

	U11	U22	U33	U12	U13	U23
O1	0.0880 (12)	0.0482 (9)	0.0541 (9)	0.0052 (8)	0.0351 (8)	−0.0034 (7)
O2	0.0704 (10)	0.0466 (9)	0.0480 (8)	−0.0046 (7)	0.0246 (8)	−0.0024 (7)
O3	0.0945 (13)	0.0603 (11)	0.0440 (9)	0.0274 (9)	−0.0025 (9)	−0.0056 (7)
O4	0.0720 (11)	0.0573 (10)	0.0373 (8)	0.0081 (8)	0.0068 (7)	−0.0042 (7)
O5	0.0824 (12)	0.0634 (10)	0.0395 (9)	0.0174 (8)	0.0101 (8)	−0.0075 (7)
N1	0.0523 (10)	0.0456 (10)	0.0383 (9)	0.0075 (8)	0.0118 (8)	−0.0051 (7)
C1	0.0769 (19)	0.102 (2)	0.0840 (19)	−0.0169 (16)	0.0350 (15)	−0.0154 (17)
C2	0.0629 (15)	0.0592 (14)	0.0482 (13)	−0.0004 (11)	0.0226 (11)	−0.0032 (11)
C3	0.104 (2)	0.087 (2)	0.0674 (17)	−0.0210 (17)	0.0350 (16)	−0.0227 (15)
C4	0.0459 (12)	0.0423 (12)	0.0453 (11)	0.0049 (9)	0.0131 (9)	−0.0042 (10)
C5	0.0466 (12)	0.0352 (11)	0.0465 (12)	0.0000 (9)	0.0120 (9)	−0.0009 (9)
C6	0.0353 (10)	0.0439 (11)	0.0399 (11)	0.0016 (9)	0.0072 (8)	−0.0001 (9)
C7	0.0433 (11)	0.0403 (11)	0.0399 (11)	0.0061 (9)	0.0071 (9)	−0.0007 (9)
C8	0.0634 (14)	0.0361 (11)	0.0548 (13)	0.0048 (10)	0.0175 (11)	0.0019 (10)
C9	0.0662 (15)	0.0485 (13)	0.0504 (13)	0.0024 (11)	0.0254 (11)	0.0041 (10)
C10	0.0796 (17)	0.0506 (14)	0.0574 (14)	−0.0129 (12)	0.0266 (13)	0.0002 (11)
C11	0.0503 (12)	0.0426 (12)	0.0384 (11)	0.0009 (10)	0.0082 (9)	0.0016 (9)
C12	0.0456 (11)	0.0357 (10)	0.0373 (11)	−0.0017 (9)	0.0123 (9)	−0.0014 (8)
C13	0.0449 (12)	0.0377 (11)	0.0413 (12)	−0.0047 (9)	0.0129 (9)	−0.0008 (9)
C14	0.0636 (15)	0.0585 (14)	0.0424 (12)	0.0162 (11)	0.0087 (10)	−0.0029 (10)
C15	0.0532 (13)	0.0428 (11)	0.0401 (12)	0.0016 (9)	0.0137 (10)	−0.0014 (9)
C16	0.0599 (14)	0.0442 (12)	0.0418 (11)	0.0064 (10)	0.0178 (10)	−0.0059 (9)
C17	0.0618 (16)	0.100 (2)	0.0716 (16)	0.0071 (14)	0.0221 (13)	−0.0198 (14)
C18	0.200 (3)	0.0501 (16)	0.099 (2)	0.0141 (18)	0.084 (2)	−0.0003 (14)

O1—C4	1.358 (2)	C6—C7	1.407 (3)
O1—C2	1.443 (3)	C7—C8	1.378 (3)
O2—C6	1.358 (2)	C7—C11	1.468 (3)
O2—C10	1.426 (2)	C8—C9	1.381 (3)
O3—C11	1.318 (2)	C8—H8	0.9300
O3—H3	0.8200	C9—H9	0.9300
O4—C13	1.251 (2)	C10—H10A	0.9600
O5—C15	1.219 (2)	C10—H10B	0.9600
N1—C13	1.335 (3)	C10—H10C	0.9600
N1—C14	1.457 (3)	C11—C12	1.375 (3)
N1—C16	1.466 (2)	C12—C15	1.446 (3)
C1—C2	1.500 (4)	C12—C13	1.457 (3)
C1—H1A	0.9600	C14—C15	1.517 (3)
C1—H1B	0.9600	C14—H14A	0.9700
C1—H1C	0.9600	C14—H14B	0.9700
C2—C3	1.500 (3)	C16—C18	1.497 (3)
C2—H2	0.9800	C16—C17	1.500 (3)
C3—H3A	0.9600	C16—H16	0.9800
C3—H3B	0.9600	C17—H17A	0.9600
C3—H3C	0.9600	C17—H17B	0.9600
C4—C5	1.387 (3)	C17—H17C	0.9600
C4—C9	1.389 (3)	C18—H18A	0.9600
C5—C6	1.380 (3)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C4—O1—C2	120.27 (16)	O2—C10—H10A	109.5
C6—O2—C10	117.91 (15)	O2—C10—H10B	109.5
C11—O3—H3	109.5	H10A—C10—H10B	109.5
C13—N1—C14	111.61 (16)	O2—C10—H10C	109.5
C13—N1—C16	124.48 (16)	H10A—C10—H10C	109.5
C14—N1—C16	123.71 (16)	H10B—C10—H10C	109.5
C2—C1—H1A	109.5	O3—C11—C12	119.05 (17)
C2—C1—H1B	109.5	O3—C11—C7	115.64 (17)
H1A—C1—H1B	109.5	C12—C11—C7	125.31 (18)
C2—C1—H1C	109.5	C11—C12—C15	131.63 (18)
H1A—C1—H1C	109.5	C11—C12—C13	120.43 (17)
H1B—C1—H1C	109.5	C15—C12—C13	107.55 (17)
O1—C2—C3	105.14 (19)	O4—C13—N1	125.12 (18)
O1—C2—C1	110.6 (2)	O4—C13—C12	124.87 (18)
C3—C2—C1	112.5 (2)	N1—C13—C12	110.00 (17)
O1—C2—H2	109.5	N1—C14—C15	104.58 (16)
C3—C2—H2	109.5	N1—C14—H14A	110.8
C1—C2—H2	109.5	C15—C14—H14A	110.8
C2—C3—H3A	109.5	N1—C14—H14B	110.8
C2—C3—H3B	109.5	C15—C14—H14B	110.8
H3A—C3—H3B	109.5	H14A—C14—H14B	108.9
C2—C3—H3C	109.5	O5—C15—C12	131.24 (19)
H3A—C3—H3C	109.5	O5—C15—C14	122.51 (18)
H3B—C3—H3C	109.5	C12—C15—C14	106.23 (16)
O1—C4—C5	114.32 (18)	N1—C16—C18	110.20 (17)
O1—C4—C9	125.52 (19)	N1—C16—C17	110.60 (18)
C5—C4—C9	120.15 (18)	C18—C16—C17	113.1 (2)
C6—C5—C4	120.53 (18)	N1—C16—H16	107.6
C6—C5—H5	119.7	C18—C16—H16	107.6
C4—C5—H5	119.7	C17—C16—H16	107.6
O2—C6—C5	123.75 (18)	C16—C17—H17A	109.5
O2—C6—C7	116.18 (17)	C16—C17—H17B	109.5
C5—C6—C7	120.04 (18)	H17A—C17—H17B	109.5
C8—C7—C6	118.08 (18)	C16—C17—H17C	109.5
C8—C7—C11	120.26 (18)	H17A—C17—H17C	109.5
C6—C7—C11	121.64 (18)	H17B—C17—H17C	109.5
C7—C8—C9	122.64 (19)	C16—C18—H18A	109.5
C7—C8—H8	118.7	C16—C18—H18B	109.5
C9—C8—H8	118.7	H18A—C18—H18B	109.5
C8—C9—C4	118.54 (19)	C16—C18—H18C	109.5
C8—C9—H9	120.7	H18A—C18—H18C	109.5
C4—C9—H9	120.7	H18B—C18—H18C	109.5
C4—O1—C2—C3	154.3 (2)	C7—C11—C12—C15	−5.9 (4)
C4—O1—C2—C1	−84.0 (2)	O3—C11—C12—C13	3.1 (3)
C2—O1—C4—C5	−171.26 (18)	C7—C11—C12—C13	−177.76 (17)
C2—O1—C4—C9	8.2 (3)	C14—N1—C13—O4	177.57 (19)
O1—C4—C5—C6	179.05 (17)	C16—N1—C13—O4	2.7 (3)
C9—C4—C5—C6	−0.4 (3)	C14—N1—C13—C12	−1.4 (2)
C10—O2—C6—C5	−3.4 (3)	C16—N1—C13—C12	−176.37 (17)
C10—O2—C6—C7	178.82 (18)	C11—C12—C13—O4	−4.9 (3)
C4—C5—C6—O2	−177.72 (17)	C15—C12—C13—O4	−178.60 (18)
C4—C5—C6—C7	0.0 (3)	C11—C12—C13—N1	174.08 (18)
O2—C6—C7—C8	177.77 (18)	C15—C12—C13—N1	0.4 (2)
C5—C6—C7—C8	−0.1 (3)	C13—N1—C14—C15	1.8 (2)
O2—C6—C7—C11	−3.5 (3)	C16—N1—C14—C15	176.78 (18)
C5—C6—C7—C11	178.64 (18)	C11—C12—C15—O5	9.5 (4)
C6—C7—C8—C9	0.7 (3)	C13—C12—C15—O5	−177.8 (2)
C11—C7—C8—C9	−178.1 (2)	C11—C12—C15—C14	−172.0 (2)
C7—C8—C9—C4	−1.1 (3)	C13—C12—C15—C14	0.7 (2)
O1—C4—C9—C8	−178.5 (2)	N1—C14—C15—O5	177.22 (19)
C5—C4—C9—C8	1.0 (3)	N1—C14—C15—C12	−1.5 (2)
C8—C7—C11—O3	126.2 (2)	C13—N1—C16—C18	−130.9 (3)
C6—C7—C11—O3	−52.5 (3)	C14—N1—C16—C18	54.8 (3)
C8—C7—C11—C12	−53.0 (3)	C13—N1—C16—C17	103.3 (2)
C6—C7—C11—C12	128.3 (2)	C14—N1—C16—C17	−71.0 (3)
O3—C11—C12—C15	175.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.80	2.555 (2)	152
C16—H16···O4	0.98	2.50	2.891 (2)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.82	1.80	2.555 (2)	152
C16—H16⋯O4	0.98	2.50	2.891 (2)	104