Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030759/si2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030759/si2023Isup2.hkl |
CCDC reference: 657671
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.155
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was obtained according to the procedure reported by Matsuo et al. (1980). Colourless single crystals of the title compound were obtained by recrystallization of 1-isopropyl-3-(α-hydroxy-2,4-diethoxylbenzylidene) pyrrolidine-2,4-dione from petroleum ether and ethyl acetate (1:3).
The hydroxyl H atom (O3)H3 was was found in a difference map and the coordinates were fixed. The other H atoms were placed in calculated positions, with C—H=0.93–0.98 Å, and included in the final cycles of refinement using a riding model, with Uiso(H)=1.2Ueq(C).
Many compounds containing the 3-acylpyrrolidine-2,4-dione system belong to heterocycles with antibiotic activity, such as tenuazonic acid (Stickings, 1959), streptolydigin (Rinehart et al., 1963), tirandamycin (MacKellar et al., 1971), malonomycin (Van Der Baan et al., 1978), α-cyclopiazonic acid (Stickings, 1959; van Rooyen et al., 1992) and β- cyclopiazonic acid (Holzapfel et al., 1970). All these compounds possess a 3-acyltetramic acid grouping as a tricarbonylmethane fragment. Most of the excellent inhibitors of p-hydroxyphenylpyruvate dioxygenase also possess similar characteristics, which are crucial for their two kinds of bioactivity (Zhu, Hu & Yang et al., 2004). In order to develop new herbicides, we synthesized the title compound. The molecular structure of the title compound is shown in Fig. 1. Atom H3, involved in intramolecular hydrogen bonding between atoms O3 and O4, was assigned to O3 rather than to O4. The C15=O4 distance is 1.264 (2) Å, which is longer than the normal carbonyl bond length (C13=O1) of 1.227 (3) Å. In contrast, the C11=O3 distance [1.320 (2) Å] is intermediate between a normal carbonyl C=O double bond and a C—O single-bond length (Allen et al., 1987) (Table 1). A similar situation was reported for 3-(1- hydroxyethylidene)-1-phenylpyrrolidine-2,4-dione (Ellis & Spek, 2001), 1-benzyl-3-(α-hydroxybenzylidene)pyrrolidine- 2,4-dione, (I) (Zhu, Song, Li et al., 2004), 1-tert-butyl-3- (α-hydroxy-4-isopropylbenzylidene)pyrrolidine-2,4-dione, (II) (Xu, 2005), and 3-(α-hydroxyl-2-methoxylbenzylidene)-1- isopropylpyrrolidine-2,4-dione, (III) (Zhu, Song, Yao et al., 2004). The dihedral angle formed by the enol ring A with the benzene ring is 41.29 (10) °, which is larger than the dihedral angles for (I), (II) (10 and 21 °, respectively) and smaller than the dihedral angle for (III) (53 °). The crystal structure of the title compound also involves two weak intramolecular C—H···O hydrogenbonding interactions (Table 2).
For related literature, see: Allen et al. (1987); Ellis & Spek (2001); Holzapfel et al. (1970); MacKellar et al. (1971); Matsuo et al. (1980); Rinehart et al. (1963); van Rooyen et al. (1992); Stickings (1959); Xu (2005); Zhu, Hu & Yang (2004); Zhu, Song, Li et al. (2004); Zhu, Song, Yao et al. (2004); Van Der Baan et al. (1978).
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.
C18H23NO5 | F(000) = 712 |
Mr = 333.37 | Dx = 1.252 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2383 reflections |
a = 13.513 (7) Å | θ = 2.8–23.7° |
b = 8.135 (4) Å | µ = 0.09 mm−1 |
c = 16.312 (8) Å | T = 294 K |
β = 99.518 (9)° | Prism, colorless |
V = 1768.5 (15) Å3 | 0.28 × 0.24 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3612 independent reflections |
Radiation source: fine-focus sealed tube | 2072 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→16 |
Tmin = 0.975, Tmax = 0.982 | k = −10→8 |
9501 measured reflections | l = −18→20 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0745P)2 + 0.2597P] where P = (Fo2 + 2Fc2)/3 |
3612 reflections | (Δ/σ)max = 0.001 |
222 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C18H23NO5 | V = 1768.5 (15) Å3 |
Mr = 333.37 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.513 (7) Å | µ = 0.09 mm−1 |
b = 8.135 (4) Å | T = 294 K |
c = 16.312 (8) Å | 0.28 × 0.24 × 0.20 mm |
β = 99.518 (9)° |
Bruker SMART CCD area-detector diffractometer | 3612 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2072 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.982 | Rint = 0.052 |
9501 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.17 e Å−3 |
3612 reflections | Δρmin = −0.21 e Å−3 |
222 parameters |
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 | 0.71221 (12) | −0.20692 (19) | 0.38809 (10) | 0.0520 (5) | |
O2 | 0.96831 (12) | −0.2405 (2) | 0.21363 (10) | 0.0562 (5) | |
O3 | 0.78362 (14) | −0.06279 (19) | 0.53402 (10) | 0.0586 (5) | |
H3 | 0.7691 | −0.0117 | 0.5737 | 0.088* | |
O4 | 0.76454 (13) | 0.16486 (19) | 0.63361 (10) | 0.0558 (5) | |
O5 | 0.88238 (16) | 0.3662 (2) | 0.39616 (10) | 0.0679 (6) | |
N1 | 0.81988 (15) | 0.4165 (2) | 0.59623 (11) | 0.0468 (5) | |
C1 | 0.85415 (16) | −0.0350 (3) | 0.41169 (12) | 0.0375 (5) | |
C2 | 0.80068 (16) | −0.1612 (3) | 0.36515 (13) | 0.0390 (5) | |
C3 | 0.83646 (17) | −0.2313 (3) | 0.29811 (13) | 0.0432 (6) | |
H3A | 0.7996 | −0.3126 | 0.2666 | 0.052* | |
C4 | 0.92752 (17) | −0.1795 (3) | 0.27832 (13) | 0.0415 (5) | |
C5 | 0.98245 (17) | −0.0563 (3) | 0.32420 (13) | 0.0435 (6) | |
H5 | 1.0437 | −0.0221 | 0.3112 | 0.052* | |
C6 | 0.94493 (16) | 0.0141 (3) | 0.38891 (13) | 0.0414 (5) | |
H6 | 0.9813 | 0.0978 | 0.4189 | 0.050* | |
C7 | 0.65284 (19) | −0.3318 (3) | 0.34169 (16) | 0.0567 (7) | |
H7A | 0.6918 | −0.4315 | 0.3400 | 0.068* | |
H7B | 0.6299 | −0.2952 | 0.2851 | 0.068* | |
C8 | 0.5653 (2) | −0.3624 (4) | 0.38525 (19) | 0.0799 (10) | |
H8A | 0.5891 | −0.4007 | 0.4407 | 0.120* | |
H8B | 0.5223 | −0.4440 | 0.3554 | 0.120* | |
H8C | 0.5284 | −0.2622 | 0.3876 | 0.120* | |
C9 | 0.9102 (2) | −0.3523 (3) | 0.15804 (17) | 0.0652 (8) | |
H9A | 0.8444 | −0.3063 | 0.1381 | 0.078* | |
H9B | 0.9018 | −0.4551 | 0.1862 | 0.078* | |
C10 | 0.9652 (3) | −0.3810 (4) | 0.08683 (19) | 0.0993 (12) | |
H10A | 0.9695 | −0.2798 | 0.0574 | 0.149* | |
H10B | 0.9297 | −0.4611 | 0.0499 | 0.149* | |
H10C | 1.0315 | −0.4206 | 0.1075 | 0.149* | |
C11 | 0.82072 (16) | 0.0394 (3) | 0.48406 (13) | 0.0397 (5) | |
C12 | 0.82908 (16) | 0.2029 (3) | 0.50607 (12) | 0.0383 (5) | |
C13 | 0.85927 (18) | 0.3479 (3) | 0.46522 (14) | 0.0468 (6) | |
C14 | 0.8572 (2) | 0.4900 (3) | 0.52583 (14) | 0.0521 (6) | |
H14A | 0.9238 | 0.5352 | 0.5428 | 0.062* | |
H14B | 0.8128 | 0.5766 | 0.5010 | 0.062* | |
C15 | 0.80136 (16) | 0.2574 (3) | 0.58414 (13) | 0.0416 (6) | |
C16 | 0.79723 (19) | 0.5096 (3) | 0.66811 (14) | 0.0510 (6) | |
H16 | 0.7915 | 0.4313 | 0.7127 | 0.061* | |
C17 | 0.8813 (2) | 0.6273 (4) | 0.69922 (18) | 0.0773 (9) | |
H17A | 0.9433 | 0.5677 | 0.7116 | 0.116* | |
H17B | 0.8677 | 0.6809 | 0.7486 | 0.116* | |
H17C | 0.8863 | 0.7081 | 0.6572 | 0.116* | |
C18 | 0.6977 (2) | 0.5972 (4) | 0.64567 (19) | 0.0783 (9) | |
H18A | 0.7012 | 0.6732 | 0.6012 | 0.118* | |
H18B | 0.6829 | 0.6558 | 0.6933 | 0.118* | |
H18C | 0.6457 | 0.5181 | 0.6282 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0456 (9) | 0.0513 (10) | 0.0616 (10) | −0.0146 (8) | 0.0164 (8) | −0.0173 (8) |
O2 | 0.0573 (10) | 0.0580 (11) | 0.0573 (10) | −0.0122 (9) | 0.0220 (9) | −0.0213 (8) |
O3 | 0.0876 (13) | 0.0431 (10) | 0.0493 (10) | −0.0178 (10) | 0.0238 (10) | −0.0030 (8) |
O4 | 0.0748 (12) | 0.0498 (10) | 0.0489 (9) | −0.0123 (9) | 0.0276 (9) | 0.0002 (8) |
O5 | 0.1104 (16) | 0.0489 (11) | 0.0530 (11) | 0.0001 (10) | 0.0384 (11) | 0.0057 (8) |
N1 | 0.0619 (13) | 0.0400 (11) | 0.0428 (11) | −0.0033 (10) | 0.0213 (10) | −0.0041 (9) |
C1 | 0.0396 (12) | 0.0346 (12) | 0.0370 (12) | −0.0010 (10) | 0.0027 (10) | −0.0004 (9) |
C2 | 0.0370 (12) | 0.0358 (12) | 0.0439 (12) | −0.0028 (10) | 0.0056 (10) | −0.0020 (10) |
C3 | 0.0450 (13) | 0.0390 (13) | 0.0447 (13) | −0.0064 (11) | 0.0048 (10) | −0.0084 (10) |
C4 | 0.0464 (13) | 0.0398 (13) | 0.0385 (12) | 0.0009 (11) | 0.0075 (10) | −0.0036 (10) |
C5 | 0.0395 (12) | 0.0457 (14) | 0.0448 (13) | −0.0032 (11) | 0.0057 (10) | −0.0027 (11) |
C6 | 0.0434 (13) | 0.0379 (12) | 0.0408 (12) | −0.0053 (10) | 0.0012 (10) | −0.0038 (10) |
C7 | 0.0503 (14) | 0.0570 (16) | 0.0634 (16) | −0.0183 (13) | 0.0112 (13) | −0.0172 (13) |
C8 | 0.0602 (18) | 0.091 (2) | 0.094 (2) | −0.0343 (17) | 0.0280 (17) | −0.0295 (18) |
C9 | 0.0723 (18) | 0.0656 (18) | 0.0611 (16) | −0.0120 (15) | 0.0208 (14) | −0.0276 (14) |
C10 | 0.116 (3) | 0.108 (3) | 0.086 (2) | −0.037 (2) | 0.052 (2) | −0.053 (2) |
C11 | 0.0410 (12) | 0.0398 (13) | 0.0376 (12) | −0.0057 (10) | 0.0047 (10) | 0.0028 (10) |
C12 | 0.0418 (12) | 0.0383 (12) | 0.0350 (11) | −0.0009 (10) | 0.0068 (10) | −0.0004 (9) |
C13 | 0.0560 (15) | 0.0431 (13) | 0.0438 (13) | 0.0018 (12) | 0.0155 (11) | 0.0014 (11) |
C14 | 0.0705 (17) | 0.0396 (14) | 0.0508 (14) | −0.0038 (12) | 0.0237 (13) | −0.0017 (11) |
C15 | 0.0445 (13) | 0.0407 (14) | 0.0402 (12) | −0.0008 (11) | 0.0082 (10) | 0.0005 (10) |
C16 | 0.0675 (17) | 0.0460 (14) | 0.0444 (13) | −0.0033 (13) | 0.0236 (13) | −0.0085 (11) |
C17 | 0.0680 (19) | 0.095 (2) | 0.0686 (18) | −0.0088 (17) | 0.0092 (15) | −0.0351 (17) |
C18 | 0.0592 (17) | 0.095 (2) | 0.087 (2) | 0.0036 (17) | 0.0316 (16) | −0.0250 (18) |
O1—C2 | 1.362 (3) | C8—H8A | 0.96 |
O1—C7 | 1.431 (3) | C8—H8B | 0.96 |
O2—C4 | 1.362 (3) | C8—H8C | 0.96 |
O2—C9 | 1.425 (3) | C9—C10 | 1.497 (4) |
O3—C11 | 1.320 (2) | C9—H9A | 0.97 |
O3—H3 | 0.82 | C9—H9B | 0.97 |
O4—C15 | 1.264 (2) | C10—H10A | 0.96 |
O5—C13 | 1.227 (3) | C10—H10B | 0.96 |
N1—C15 | 1.327 (3) | C10—H10C | 0.96 |
N1—C14 | 1.456 (3) | C11—C12 | 1.378 (3) |
N1—C16 | 1.470 (3) | C12—C13 | 1.446 (3) |
C1—C6 | 1.397 (3) | C12—C15 | 1.455 (3) |
C1—C2 | 1.404 (3) | C13—C14 | 1.524 (3) |
C1—C11 | 1.463 (3) | C14—H14A | 0.97 |
C2—C3 | 1.389 (3) | C14—H14B | 0.97 |
C3—C4 | 1.388 (3) | C16—C17 | 1.508 (4) |
C3—H3A | 0.93 | C16—C18 | 1.513 (4) |
C4—C5 | 1.390 (3) | C16—H16 | 0.98 |
C5—C6 | 1.370 (3) | C17—H17A | 0.96 |
C5—H5 | 0.93 | C17—H17B | 0.96 |
C6—H6 | 0.93 | C17—H17C | 0.96 |
C7—C8 | 1.498 (3) | C18—H18A | 0.96 |
C7—H7A | 0.97 | C18—H18B | 0.96 |
C7—H7B | 0.97 | C18—H18C | 0.96 |
C2—O1—C7 | 119.30 (17) | C9—C10—H10A | 109.5 |
C4—O2—C9 | 118.34 (18) | C9—C10—H10B | 109.5 |
C11—O3—H3 | 109.5 | H10A—C10—H10B | 109.5 |
C15—N1—C14 | 111.37 (17) | C9—C10—H10C | 109.5 |
C15—N1—C16 | 124.19 (18) | H10A—C10—H10C | 109.5 |
C14—N1—C16 | 124.24 (19) | H10B—C10—H10C | 109.5 |
C6—C1—C2 | 117.45 (19) | O3—C11—C12 | 118.06 (19) |
C6—C1—C11 | 119.89 (19) | O3—C11—C1 | 115.94 (19) |
C2—C1—C11 | 122.59 (19) | C12—C11—C1 | 125.92 (19) |
O1—C2—C3 | 122.64 (19) | C11—C12—C13 | 133.2 (2) |
O1—C2—C1 | 116.61 (18) | C11—C12—C15 | 120.02 (19) |
C3—C2—C1 | 120.7 (2) | C13—C12—C15 | 106.74 (19) |
C4—C3—C2 | 119.7 (2) | O5—C13—C12 | 131.0 (2) |
C4—C3—H3A | 120.1 | O5—C13—C14 | 122.6 (2) |
C2—C3—H3A | 120.1 | C12—C13—C14 | 106.41 (18) |
O2—C4—C3 | 123.9 (2) | N1—C14—C13 | 104.27 (18) |
O2—C4—C5 | 115.5 (2) | N1—C14—H14A | 110.9 |
C3—C4—C5 | 120.6 (2) | C13—C14—H14A | 110.9 |
C6—C5—C4 | 118.9 (2) | N1—C14—H14B | 110.9 |
C6—C5—H5 | 120.5 | C13—C14—H14B | 110.9 |
C4—C5—H5 | 120.5 | H14A—C14—H14B | 108.9 |
C5—C6—C1 | 122.6 (2) | O4—C15—N1 | 124.8 (2) |
C5—C6—H6 | 118.7 | O4—C15—C12 | 124.3 (2) |
C1—C6—H6 | 118.7 | N1—C15—C12 | 110.95 (19) |
O1—C7—C8 | 106.6 (2) | N1—C16—C17 | 110.5 (2) |
O1—C7—H7A | 110.4 | N1—C16—C18 | 110.1 (2) |
C8—C7—H7A | 110.4 | C17—C16—C18 | 111.9 (2) |
O1—C7—H7B | 110.4 | N1—C16—H16 | 108.1 |
C8—C7—H7B | 110.4 | C17—C16—H16 | 108.1 |
H7A—C7—H7B | 108.6 | C18—C16—H16 | 108.1 |
C7—C8—H8A | 109.5 | C16—C17—H17A | 109.5 |
C7—C8—H8B | 109.5 | C16—C17—H17B | 109.5 |
H8A—C8—H8B | 109.5 | H17A—C17—H17B | 109.5 |
C7—C8—H8C | 109.5 | C16—C17—H17C | 109.5 |
H8A—C8—H8C | 109.5 | H17A—C17—H17C | 109.5 |
H8B—C8—H8C | 109.5 | H17B—C17—H17C | 109.5 |
O2—C9—C10 | 107.6 (2) | C16—C18—H18A | 109.5 |
O2—C9—H9A | 110.2 | C16—C18—H18B | 109.5 |
C10—C9—H9A | 110.2 | H18A—C18—H18B | 109.5 |
O2—C9—H9B | 110.2 | C16—C18—H18C | 109.5 |
C10—C9—H9B | 110.2 | H18A—C18—H18C | 109.5 |
H9A—C9—H9B | 108.5 | H18B—C18—H18C | 109.5 |
C7—O1—C2—C3 | −0.2 (3) | C1—C11—C12—C13 | 8.0 (4) |
C7—O1—C2—C1 | 178.3 (2) | O3—C11—C12—C15 | 2.6 (3) |
C6—C1—C2—O1 | −179.79 (19) | C1—C11—C12—C15 | −174.09 (19) |
C11—C1—C2—O1 | 3.1 (3) | C11—C12—C13—O5 | 3.6 (5) |
C6—C1—C2—C3 | −1.3 (3) | C15—C12—C13—O5 | −174.5 (3) |
C11—C1—C2—C3 | −178.3 (2) | C11—C12—C13—C14 | −177.0 (2) |
O1—C2—C3—C4 | −179.7 (2) | C15—C12—C13—C14 | 4.8 (2) |
C1—C2—C3—C4 | 1.9 (3) | C15—N1—C14—C13 | 0.1 (3) |
C9—O2—C4—C3 | 6.3 (3) | C16—N1—C14—C13 | −174.9 (2) |
C9—O2—C4—C5 | −172.4 (2) | O5—C13—C14—N1 | 176.3 (2) |
C2—C3—C4—O2 | −179.7 (2) | C12—C13—C14—N1 | −3.1 (3) |
C2—C3—C4—C5 | −1.0 (3) | C14—N1—C15—O4 | −176.9 (2) |
O2—C4—C5—C6 | 178.33 (19) | C16—N1—C15—O4 | −1.9 (4) |
C3—C4—C5—C6 | −0.4 (3) | C14—N1—C15—C12 | 3.0 (3) |
C4—C5—C6—C1 | 1.1 (3) | C16—N1—C15—C12 | 178.0 (2) |
C2—C1—C6—C5 | −0.2 (3) | C11—C12—C15—O4 | −3.5 (3) |
C11—C1—C6—C5 | 176.9 (2) | C13—C12—C15—O4 | 174.9 (2) |
C2—O1—C7—C8 | 176.1 (2) | C11—C12—C15—N1 | 176.5 (2) |
C4—O2—C9—C10 | 172.0 (2) | C13—C12—C15—N1 | −5.1 (2) |
C6—C1—C11—O3 | −136.5 (2) | C15—N1—C16—C17 | 139.1 (2) |
C2—C1—C11—O3 | 40.5 (3) | C14—N1—C16—C17 | −46.6 (3) |
C6—C1—C11—C12 | 40.2 (3) | C15—N1—C16—C18 | −96.8 (3) |
C2—C1—C11—C12 | −142.8 (2) | C14—N1—C16—C18 | 77.5 (3) |
O3—C11—C12—C13 | −175.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 1.74 | 2.505 (2) | 154 |
C6—H6···O5 | 0.93 | 2.56 | 2.994 (3) | 109 |
C16—H16···O4 | 0.98 | 2.52 | 2.880 (3) | 102 |
Experimental details
Crystal data | |
Chemical formula | C18H23NO5 |
Mr | 333.37 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 13.513 (7), 8.135 (4), 16.312 (8) |
β (°) | 99.518 (9) |
V (Å3) | 1768.5 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.28 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.975, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9501, 3612, 2072 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.156, 1.00 |
No. of reflections | 3612 |
No. of parameters | 222 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.21 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 1.74 | 2.505 (2) | 153.5 |
C6—H6···O5 | 0.93 | 2.56 | 2.994 (3) | 109 |
C16—H16···O4 | 0.98 | 2.52 | 2.880 (3) | 102 |
Many compounds containing the 3-acylpyrrolidine-2,4-dione system belong to heterocycles with antibiotic activity, such as tenuazonic acid (Stickings, 1959), streptolydigin (Rinehart et al., 1963), tirandamycin (MacKellar et al., 1971), malonomycin (Van Der Baan et al., 1978), α-cyclopiazonic acid (Stickings, 1959; van Rooyen et al., 1992) and β- cyclopiazonic acid (Holzapfel et al., 1970). All these compounds possess a 3-acyltetramic acid grouping as a tricarbonylmethane fragment. Most of the excellent inhibitors of p-hydroxyphenylpyruvate dioxygenase also possess similar characteristics, which are crucial for their two kinds of bioactivity (Zhu, Hu & Yang et al., 2004). In order to develop new herbicides, we synthesized the title compound. The molecular structure of the title compound is shown in Fig. 1. Atom H3, involved in intramolecular hydrogen bonding between atoms O3 and O4, was assigned to O3 rather than to O4. The C15=O4 distance is 1.264 (2) Å, which is longer than the normal carbonyl bond length (C13=O1) of 1.227 (3) Å. In contrast, the C11=O3 distance [1.320 (2) Å] is intermediate between a normal carbonyl C=O double bond and a C—O single-bond length (Allen et al., 1987) (Table 1). A similar situation was reported for 3-(1- hydroxyethylidene)-1-phenylpyrrolidine-2,4-dione (Ellis & Spek, 2001), 1-benzyl-3-(α-hydroxybenzylidene)pyrrolidine- 2,4-dione, (I) (Zhu, Song, Li et al., 2004), 1-tert-butyl-3- (α-hydroxy-4-isopropylbenzylidene)pyrrolidine-2,4-dione, (II) (Xu, 2005), and 3-(α-hydroxyl-2-methoxylbenzylidene)-1- isopropylpyrrolidine-2,4-dione, (III) (Zhu, Song, Yao et al., 2004). The dihedral angle formed by the enol ring A with the benzene ring is 41.29 (10) °, which is larger than the dihedral angles for (I), (II) (10 and 21 °, respectively) and smaller than the dihedral angle for (III) (53 °). The crystal structure of the title compound also involves two weak intramolecular C—H···O hydrogenbonding interactions (Table 2).