1-Benzyl-3-(α-hydroxy­benzyl­idene)­pyrrolidine-2,4-dione

The title compound, C₁₈H₁₅NO₃, is a potent new herbicide containing the pyrrolidine-2,4-dione ring system. In the crystalline state, the molecular skeleton contains one enol hydrogen-bonded moiety, formed from benzoyl C=O isomerization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.059
• wR factor = 0.131
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C2
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.39
           From the CIF: _reflns_number_total               1830
           Count of symmetry unique reflns         1832
           Completeness (_total/calc)             99.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-Benzyl-3-(α-hydroxybenzylidene)pyrrolidine-2,4-dione

Crystal data

C18H15NO3	F(000) = 616
Mr = 293.31	Dx = 1.273 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 765 reflections
a = 5.569 (3) Å	θ = 2.6–19.6°
b = 15.062 (7) Å	µ = 0.09 mm^−1
c = 18.245 (9) Å	T = 293 K
V = 1530.3 (12) Å^3	Prism, colourless
Z = 4	0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 26.4°, θmin = 2.2°
φ and ω scans	h = −6→5
8033 measured reflections	k = −14→18
1830 independent reflections	l = −22→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0612P)^2] where P = (Fo^2 + 2Fc^2)/3
1830 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4162 (5)	0.93032 (19)	0.50795 (15)	0.0538 (8)
O1	0.0652 (6)	0.8564 (2)	0.69333 (15)	0.0827 (10)
H1	0.0445	0.8981	0.6650	0.124*
O2	0.1031 (5)	0.96084 (19)	0.58696 (14)	0.0748 (9)
O3	0.6987 (5)	0.7356 (2)	0.57159 (17)	0.0971 (11)
C1	0.2485 (7)	0.8076 (3)	0.67039 (19)	0.0549 (10)
C2	0.2854 (7)	0.7274 (3)	0.71659 (19)	0.0569 (10)
C3	0.1150 (8)	0.7062 (3)	0.7693 (2)	0.0825 (14)
H3	−0.0187	0.7425	0.7749	0.099*
C4	0.1397 (10)	0.6317 (4)	0.8139 (3)	0.0948 (16)
H4	0.0225	0.6187	0.8486	0.114*
C5	0.3339 (10)	0.5779 (4)	0.8070 (3)	0.0899 (16)
H5	0.3480	0.5276	0.8362	0.108*
C6	0.5088 (11)	0.5978 (4)	0.7572 (3)	0.0977 (17)
H6	0.6438	0.5617	0.7534	0.117*
C7	0.4859 (9)	0.6726 (3)	0.7114 (2)	0.0854 (15)
H7	0.6056	0.6855	0.6775	0.102*
C8	0.3718 (6)	0.8355 (2)	0.60767 (18)	0.0468 (9)
C9	0.2828 (6)	0.9146 (3)	0.5680 (2)	0.0512 (9)
C10	0.6063 (7)	0.8650 (3)	0.4991 (2)	0.0593 (10)
H10A	0.7630	0.8931	0.5009	0.071*
H10B	0.5902	0.8339	0.4528	0.071*
C11	0.5726 (7)	0.8011 (3)	0.5638 (2)	0.0585 (10)
C12	0.3516 (7)	0.9935 (3)	0.4494 (2)	0.0672 (11)
H12A	0.2121	1.0274	0.4646	0.081*
H12B	0.3085	0.9606	0.4056	0.081*
C13	0.5537 (7)	1.0570 (2)	0.4312 (2)	0.0558 (10)
C14	0.6461 (9)	1.1135 (3)	0.4836 (2)	0.0789 (13)
H14	0.5838	1.1123	0.5309	0.095*
C15	0.8302 (9)	1.1720 (3)	0.4669 (3)	0.0902 (15)
H15	0.8895	1.2098	0.5029	0.108*
C16	0.9255 (9)	1.1746 (3)	0.3977 (3)	0.0869 (14)
H16	1.0484	1.2141	0.3866	0.104*
C17	0.8380 (10)	1.1183 (4)	0.3452 (3)	0.0973 (17)
H17	0.9020	1.1196	0.2981	0.117*
C18	0.6546 (9)	1.0595 (4)	0.3618 (2)	0.0853 (15)
H18	0.5983	1.0211	0.3257	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0539 (17)	0.0435 (18)	0.0639 (18)	−0.0008 (16)	−0.0018 (16)	0.0038 (15)
O1	0.089 (2)	0.080 (2)	0.0790 (19)	0.023 (2)	0.0202 (17)	0.0071 (17)
O2	0.0816 (19)	0.062 (2)	0.0811 (18)	0.0281 (18)	0.0110 (16)	0.0005 (15)
O3	0.098 (2)	0.073 (2)	0.120 (2)	0.044 (2)	0.0348 (19)	0.033 (2)
C1	0.054 (2)	0.051 (2)	0.059 (2)	0.001 (2)	−0.003 (2)	−0.010 (2)
C2	0.060 (2)	0.057 (3)	0.053 (2)	−0.012 (2)	−0.009 (2)	0.003 (2)
C3	0.079 (3)	0.081 (4)	0.087 (3)	−0.004 (3)	0.004 (3)	0.016 (3)
C4	0.093 (4)	0.097 (4)	0.094 (3)	−0.020 (4)	0.009 (3)	0.025 (3)
C5	0.111 (4)	0.077 (4)	0.081 (3)	−0.025 (4)	−0.020 (3)	0.027 (3)
C6	0.109 (4)	0.082 (4)	0.102 (3)	0.005 (3)	−0.004 (3)	0.029 (3)
C7	0.089 (3)	0.084 (4)	0.083 (3)	0.010 (3)	0.004 (3)	0.026 (3)
C8	0.052 (2)	0.037 (2)	0.0516 (19)	0.0021 (18)	−0.0037 (18)	−0.0056 (18)
C9	0.052 (2)	0.040 (2)	0.061 (2)	−0.0007 (19)	−0.005 (2)	−0.0107 (19)
C10	0.048 (2)	0.055 (2)	0.075 (2)	−0.004 (2)	0.004 (2)	0.002 (2)
C11	0.055 (2)	0.044 (2)	0.076 (2)	−0.002 (2)	−0.001 (2)	0.001 (2)
C12	0.067 (3)	0.065 (3)	0.069 (2)	−0.001 (2)	−0.012 (2)	0.009 (2)
C13	0.064 (2)	0.043 (2)	0.061 (2)	0.012 (2)	−0.002 (2)	0.010 (2)
C14	0.107 (4)	0.057 (3)	0.072 (3)	−0.011 (3)	0.013 (3)	−0.005 (2)
C15	0.110 (4)	0.054 (3)	0.107 (4)	−0.023 (3)	0.005 (3)	−0.006 (3)
C16	0.085 (3)	0.063 (3)	0.113 (4)	−0.007 (3)	0.015 (3)	0.033 (3)
C17	0.111 (4)	0.106 (4)	0.075 (3)	−0.015 (4)	0.021 (3)	0.020 (3)
C18	0.105 (4)	0.087 (4)	0.064 (3)	−0.010 (3)	0.000 (3)	0.004 (3)

Geometric parameters (Å, º)

N1—C9	1.345 (4)	C8—C11	1.469 (5)
N1—C10	1.454 (5)	C8—C9	1.479 (5)
N1—C12	1.475 (4)	C10—C11	1.535 (5)
O1—C1	1.326 (4)	C10—H10A	0.9700
O1—H1	0.8200	C10—H10B	0.9700
O2—C9	1.268 (4)	C12—C13	1.514 (6)
O3—C11	1.219 (5)	C12—H12A	0.9700
C1—C8	1.399 (5)	C12—H12B	0.9700
C1—C2	1.487 (5)	C13—C14	1.379 (6)
C2—C3	1.388 (5)	C13—C18	1.387 (5)
C2—C7	1.392 (6)	C14—C15	1.386 (7)
C3—C4	1.393 (6)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.369 (6)
C4—C5	1.357 (7)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.369 (7)
C5—C6	1.366 (7)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.386 (7)
C6—C7	1.408 (6)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300
C9—N1—C10	111.9 (3)	N1—C10—H10A	110.9
C9—N1—C12	124.7 (3)	C11—C10—H10A	110.9
C10—N1—C12	122.2 (3)	N1—C10—H10B	110.9
C1—O1—H1	109.5	C11—C10—H10B	110.9
O1—C1—C8	118.0 (3)	H10A—C10—H10B	108.9
O1—C1—C2	112.2 (3)	O3—C11—C8	131.3 (4)
C8—C1—C2	129.8 (4)	O3—C11—C10	121.8 (4)
C3—C2—C7	117.3 (4)	C8—C11—C10	106.9 (3)
C3—C2—C1	119.1 (4)	N1—C12—C13	112.6 (3)
C7—C2—C1	123.7 (4)	N1—C12—H12A	109.1
C2—C3—C4	121.6 (5)	C13—C12—H12A	109.1
C2—C3—H3	119.2	N1—C12—H12B	109.1
C4—C3—H3	119.2	C13—C12—H12B	109.1
C5—C4—C3	120.3 (5)	H12A—C12—H12B	107.8
C5—C4—H4	119.8	C14—C13—C18	117.7 (4)
C3—C4—H4	119.8	C14—C13—C12	121.0 (4)
C4—C5—C6	120.0 (5)	C18—C13—C12	121.2 (4)
C4—C5—H5	120.0	C13—C14—C15	121.1 (4)
C6—C5—H5	120.0	C13—C14—H14	119.5
C5—C6—C7	120.4 (5)	C15—C14—H14	119.5
C5—C6—H6	119.8	C16—C15—C14	120.5 (5)
C7—C6—H6	119.8	C16—C15—H15	119.8
C2—C7—C6	120.5 (4)	C14—C15—H15	119.8
C2—C7—H7	119.8	C17—C16—C15	119.4 (5)
C6—C7—H7	119.8	C17—C16—H16	120.3
C1—C8—C11	135.5 (4)	C15—C16—H16	120.3
C1—C8—C9	118.5 (3)	C16—C17—C18	120.3 (5)
C11—C8—C9	105.8 (3)	C16—C17—H17	119.8
O2—C9—N1	124.1 (4)	C18—C17—H17	119.8
O2—C9—C8	125.0 (3)	C17—C18—C13	121.0 (5)
N1—C9—C8	110.8 (3)	C17—C18—H18	119.5
N1—C10—C11	104.4 (3)	C13—C18—H18	119.5
O1—C1—C2—C3	8.6 (5)	C1—C8—C9—N1	−177.9 (3)
C8—C1—C2—C3	−169.4 (4)	C11—C8—C9—N1	−2.1 (4)
O1—C1—C2—C7	−169.8 (4)	C9—N1—C10—C11	1.1 (4)
C8—C1—C2—C7	12.1 (6)	C12—N1—C10—C11	−167.2 (3)
C7—C2—C3—C4	−1.7 (6)	C1—C8—C11—O3	−2.1 (7)
C1—C2—C3—C4	179.7 (4)	C9—C8—C11—O3	−176.8 (4)
C2—C3—C4—C5	0.4 (7)	C1—C8—C11—C10	177.4 (4)
C3—C4—C5—C6	1.4 (8)	C9—C8—C11—C10	2.6 (4)
C4—C5—C6—C7	−1.7 (8)	N1—C10—C11—O3	177.2 (4)
C3—C2—C7—C6	1.4 (7)	N1—C10—C11—C8	−2.3 (4)
C1—C2—C7—C6	179.9 (4)	C9—N1—C12—C13	129.4 (4)
C5—C6—C7—C2	0.3 (8)	C10—N1—C12—C13	−63.9 (4)
O1—C1—C8—C11	−177.8 (4)	N1—C12—C13—C14	−60.2 (5)
C2—C1—C8—C11	0.1 (7)	N1—C12—C13—C18	118.9 (4)
O1—C1—C8—C9	−3.6 (5)	C18—C13—C14—C15	1.3 (7)
C2—C1—C8—C9	174.4 (3)	C12—C13—C14—C15	−179.6 (4)
C10—N1—C9—O2	−178.4 (3)	C13—C14—C15—C16	−0.4 (8)
C12—N1—C9—O2	−10.5 (5)	C14—C15—C16—C17	−0.4 (8)
C10—N1—C9—C8	0.6 (4)	C15—C16—C17—C18	0.1 (8)
C12—N1—C9—C8	168.5 (3)	C16—C17—C18—C13	0.9 (8)
C1—C8—C9—O2	1.2 (5)	C14—C13—C18—C17	−1.6 (7)
C11—C8—C9—O2	177.0 (3)	C12—C13—C18—C17	179.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O3^i	0.97	2.46	3.019 (5)	116
O1—H1···O2	0.82	1.74	2.507 (4)	155
C3—H3···O1	0.93	2.32	2.669 (6)	102
C7—H7···O3	0.93	2.14	2.969 (6)	148
C12—H12A···O2	0.97	2.52	2.908 (5)	104

Symmetry code: (i) x−1/2, −y+3/2, −z+1.