1-Benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate.

The pyrrolidine-2,5-dione ring in the title compound, C(15)H(15)NO(6), is in a twisted conformation with the acetyl C atoms projecting to opposite sides of the ring. The acetyl groups lie to opposite sides of the five-membered ring. The benzene ring is roughly perpendicular to the heterocyclic ring, forming a dihedral angle of 76.57 (14)° with it. In the crystal, mol-ecules are connected through a network of C-H⋯O and C-H⋯π inter-actions.

Related literature

For the use of N-acyl­iminium in organic synthesis, see: Vieira et al. (2008 ▶); Huang (2006 ▶); Russo et al. (2010 ▶). For background to the synthesis, see: Caracelli et al. (2010 ▶). For a related structure, see: Naz et al. (2009 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶); Iulek & Zukerman-Schpector (1997 ▶).

Experimental

Crystal data

C15H15NO6

M = 305.28

Orthorhombic,

a = 8.8498 (4) Å

b = 9.8107 (4) Å

c = 17.5148 (6) Å

V = 1520.68 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 290 K

0.28 × 0.23 × 0.06 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.962, T max = 0.991

7672 measured reflections

1541 independent reflections

1396 reflections with I > 2σ(I)

R int = 0.122

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.085

S = 1.07

1541 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043187/hg2732sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043187/hg2732Isup2.hkl

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

C15H15NO6	F(000) = 640
Mr = 305.28	Dx = 1.333 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5560 reflections
a = 8.8498 (4) Å	θ = 2.9–26.4°
b = 9.8107 (4) Å	µ = 0.10 mm−1
c = 17.5148 (6) Å	T = 290 K
V = 1520.68 (11) Å3	Block, colourless
Z = 4	0.28 × 0.23 × 0.06 mm

Bruker SMART APEXII diffractometer	1541 independent reflections
Radiation source: fine-focus sealed tube	1396 reflections with I > 2σ(I)
graphite	Rint = 0.122
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.962, Tmax = 0.991	k = −10→11
7672 measured reflections	l = −20→20

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0293P)2 + 0.1923P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1541 reflections	Δρmax = 0.12 e Å−3
202 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.111 (10)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.25814 (16)	0.67116 (18)	0.09591 (10)	0.0555 (5)
O2	0.42326 (15)	0.75768 (16)	−0.03939 (9)	0.0425 (4)
O3	0.57172 (17)	0.60872 (18)	0.02191 (10)	0.0505 (4)
O4	0.5859 (2)	1.03936 (19)	0.03516 (11)	0.0652 (6)
O5	0.3864 (3)	1.1015 (2)	0.10556 (14)	0.0772 (6)
O6	0.6412 (2)	0.93139 (18)	0.18931 (10)	0.0603 (5)
N1	0.44087 (19)	0.79166 (19)	0.15977 (11)	0.0418 (5)
C1	0.3594 (2)	0.7537 (2)	0.09654 (13)	0.0415 (5)
C2	0.4146 (2)	0.8367 (2)	0.02866 (13)	0.0400 (5)
H2	0.3419	0.9104	0.0199	0.048*
C3	0.5611 (2)	0.9008 (2)	0.05719 (14)	0.0448 (5)
H3	0.6453	0.8463	0.0374	0.054*
C4	0.5564 (2)	0.8820 (2)	0.14324 (14)	0.0437 (5)
C5	0.4073 (3)	0.7405 (3)	0.23638 (14)	0.0510 (6)
H5A	0.4951	0.7538	0.2687	0.061*
H5B	0.3875	0.6434	0.2336	0.061*
C6	0.2737 (3)	0.8104 (2)	0.27199 (13)	0.0482 (6)
C7	0.1408 (3)	0.7410 (3)	0.28440 (16)	0.0629 (7)
H7	0.1336	0.6495	0.2708	0.075*
C8	0.0181 (4)	0.8059 (4)	0.3169 (2)	0.0835 (10)
H8	−0.0709	0.7579	0.3254	0.100*
C9	0.0272 (5)	0.9408 (4)	0.3365 (2)	0.0896 (12)
H9	−0.0554	0.9845	0.3584	0.108*
C10	0.1573 (5)	1.0103 (4)	0.3238 (2)	0.0956 (12)
H10	0.1636	1.1019	0.3370	0.115*
C11	0.2808 (4)	0.9457 (3)	0.2914 (2)	0.0748 (9)
H11	0.3693	0.9944	0.2828	0.090*
C12	0.5071 (2)	0.6412 (2)	−0.03556 (14)	0.0425 (5)
C13	0.5040 (3)	0.5656 (3)	−0.10878 (16)	0.0586 (7)
H13A	0.5864	0.5020	−0.1102	0.088*
H13B	0.5135	0.6287	−0.1504	0.088*
H13C	0.4102	0.5172	−0.1132	0.088*
C14	0.4873 (5)	1.1318 (3)	0.06372 (18)	0.0722 (9)
C15	0.5247 (7)	1.2725 (3)	0.0367 (3)	0.1274 (19)
H15A	0.4450	1.3338	0.0509	0.191*
H15B	0.5355	1.2721	−0.0178	0.191*
H15C	0.6177	1.3018	0.0597	0.191*

	U11	U22	U33	U12	U13	U23
O1	0.0492 (8)	0.0622 (11)	0.0550 (11)	−0.0163 (8)	0.0025 (7)	0.0034 (9)
O2	0.0459 (7)	0.0426 (8)	0.0388 (8)	0.0016 (7)	−0.0020 (6)	−0.0024 (7)
O3	0.0532 (8)	0.0470 (9)	0.0514 (10)	0.0047 (8)	−0.0038 (8)	0.0011 (8)
O4	0.0894 (13)	0.0503 (10)	0.0558 (11)	−0.0256 (10)	0.0064 (10)	0.0006 (9)
O5	0.1066 (15)	0.0511 (11)	0.0739 (14)	0.0153 (12)	0.0061 (13)	−0.0027 (11)
O6	0.0602 (10)	0.0644 (11)	0.0562 (11)	−0.0106 (9)	−0.0110 (8)	−0.0119 (10)
N1	0.0427 (9)	0.0433 (10)	0.0395 (10)	0.0004 (8)	−0.0002 (7)	−0.0005 (9)
C1	0.0390 (10)	0.0409 (11)	0.0445 (12)	0.0007 (10)	0.0029 (9)	−0.0015 (11)
C2	0.0417 (10)	0.0394 (11)	0.0390 (11)	0.0005 (9)	0.0015 (9)	−0.0021 (10)
C3	0.0473 (11)	0.0414 (11)	0.0457 (13)	−0.0088 (10)	0.0046 (10)	−0.0064 (11)
C4	0.0438 (11)	0.0408 (12)	0.0465 (12)	0.0000 (11)	−0.0002 (10)	−0.0050 (10)
C5	0.0585 (12)	0.0517 (13)	0.0428 (12)	0.0063 (12)	0.0029 (10)	0.0077 (12)
C6	0.0628 (13)	0.0482 (12)	0.0337 (12)	0.0064 (12)	0.0026 (10)	0.0025 (11)
C7	0.0716 (15)	0.0587 (15)	0.0584 (17)	0.0038 (15)	0.0144 (13)	0.0088 (15)
C8	0.0765 (18)	0.101 (3)	0.073 (2)	0.016 (2)	0.0284 (16)	0.018 (2)
C9	0.104 (3)	0.100 (3)	0.0645 (19)	0.048 (2)	0.0299 (18)	0.007 (2)
C10	0.134 (3)	0.071 (2)	0.082 (2)	0.024 (2)	0.022 (2)	−0.019 (2)
C11	0.0864 (19)	0.0607 (16)	0.077 (2)	0.0022 (17)	0.0113 (17)	−0.0182 (17)
C12	0.0421 (10)	0.0384 (12)	0.0469 (13)	−0.0025 (10)	0.0043 (10)	−0.0014 (10)
C13	0.0644 (14)	0.0558 (15)	0.0557 (15)	−0.0018 (14)	0.0033 (12)	−0.0154 (14)
C14	0.123 (3)	0.0413 (14)	0.0525 (16)	−0.0093 (17)	−0.0130 (19)	0.0001 (14)
C15	0.246 (6)	0.0468 (18)	0.090 (3)	−0.032 (3)	−0.023 (3)	0.0162 (19)

O1—C1	1.208 (2)	C6—C11	1.372 (4)
O2—C12	1.365 (3)	C6—C7	1.376 (4)
O2—C2	1.424 (3)	C7—C8	1.382 (4)
O3—C12	1.201 (3)	C7—H7	0.9300
O4—C14	1.354 (4)	C8—C9	1.370 (5)
O4—C3	1.430 (3)	C8—H8	0.9300
O5—C14	1.193 (4)	C9—C10	1.356 (6)
O6—C4	1.204 (3)	C9—H9	0.9300
N1—C1	1.373 (3)	C10—C11	1.385 (5)
N1—C4	1.384 (3)	C10—H10	0.9300
N1—C5	1.463 (3)	C11—H11	0.9300
C1—C2	1.522 (3)	C12—C13	1.481 (3)
C2—C3	1.525 (3)	C13—H13A	0.9600
C2—H2	0.9800	C13—H13B	0.9600
C3—C4	1.519 (3)	C13—H13C	0.9600
C3—H3	0.9800	C14—C15	1.496 (4)
C5—C6	1.502 (3)	C15—H15A	0.9600
C5—H5A	0.9700	C15—H15B	0.9600
C5—H5B	0.9700	C15—H15C	0.9600
C12—O2—C2	116.37 (16)	C6—C7—H7	119.7
C14—O4—C3	116.0 (2)	C8—C7—H7	119.7
C1—N1—C4	113.15 (19)	C9—C8—C7	120.2 (4)
C1—N1—C5	122.70 (18)	C9—C8—H8	119.9
C4—N1—C5	124.15 (19)	C7—C8—H8	119.9
O1—C1—N1	125.4 (2)	C10—C9—C8	119.6 (3)
O1—C1—C2	126.2 (2)	C10—C9—H9	120.2
N1—C1—C2	108.44 (17)	C8—C9—H9	120.2
O2—C2—C1	112.34 (17)	C9—C10—C11	120.5 (3)
O2—C2—C3	116.94 (17)	C9—C10—H10	119.8
C1—C2—C3	103.76 (18)	C11—C10—H10	119.8
O2—C2—H2	107.8	C6—C11—C10	120.5 (3)
C1—C2—H2	107.8	C6—C11—H11	119.7
C3—C2—H2	107.8	C10—C11—H11	119.7
O4—C3—C4	112.8 (2)	O3—C12—O2	121.5 (2)
O4—C3—C2	115.7 (2)	O3—C12—C13	127.0 (2)
C4—C3—C2	104.60 (18)	O2—C12—C13	111.5 (2)
O4—C3—H3	107.8	C12—C13—H13A	109.5
C4—C3—H3	107.8	C12—C13—H13B	109.5
C2—C3—H3	107.8	H13A—C13—H13B	109.5
O6—C4—N1	125.3 (2)	C12—C13—H13C	109.5
O6—C4—C3	126.8 (2)	H13A—C13—H13C	109.5
N1—C4—C3	107.78 (18)	H13B—C13—H13C	109.5
N1—C5—C6	112.58 (19)	O5—C14—O4	122.9 (3)
N1—C5—H5A	109.1	O5—C14—C15	126.1 (4)
C6—C5—H5A	109.1	O4—C14—C15	111.0 (4)
N1—C5—H5B	109.1	C14—C15—H15A	109.5
C6—C5—H5B	109.1	C14—C15—H15B	109.5
H5A—C5—H5B	107.8	H15A—C15—H15B	109.5
C11—C6—C7	118.6 (3)	C14—C15—H15C	109.5
C11—C6—C5	120.5 (3)	H15A—C15—H15C	109.5
C7—C6—C5	120.8 (2)	H15B—C15—H15C	109.5
C6—C7—C8	120.6 (3)
C4—N1—C1—O1	176.2 (2)	O4—C3—C4—O6	−44.1 (3)
C5—N1—C1—O1	−3.7 (3)	C2—C3—C4—O6	−170.7 (2)
C4—N1—C1—C2	−5.8 (2)	O4—C3—C4—N1	138.79 (19)
C5—N1—C1—C2	174.33 (19)	C2—C3—C4—N1	12.2 (2)
C12—O2—C2—C1	−54.5 (2)	C1—N1—C5—C6	−77.9 (3)
C12—O2—C2—C3	65.3 (2)	C4—N1—C5—C6	102.2 (2)
O1—C1—C2—O2	−41.8 (3)	N1—C5—C6—C11	−67.2 (3)
N1—C1—C2—O2	140.22 (17)	N1—C5—C6—C7	111.6 (3)
O1—C1—C2—C3	−169.0 (2)	C11—C6—C7—C8	−1.0 (5)
N1—C1—C2—C3	13.0 (2)	C5—C6—C7—C8	−179.7 (3)
C14—O4—C3—C4	−55.3 (3)	C6—C7—C8—C9	0.6 (5)
C14—O4—C3—C2	65.1 (3)	C7—C8—C9—C10	0.0 (6)
O2—C2—C3—O4	96.2 (2)	C8—C9—C10—C11	−0.2 (6)
C1—C2—C3—O4	−139.5 (2)	C7—C6—C11—C10	0.9 (5)
O2—C2—C3—C4	−139.1 (2)	C5—C6—C11—C10	179.6 (3)
C1—C2—C3—C4	−14.8 (2)	C9—C10—C11—C6	−0.3 (6)
C1—N1—C4—O6	178.6 (2)	C2—O2—C12—O3	−1.1 (3)
C5—N1—C4—O6	−1.5 (3)	C2—O2—C12—C13	178.27 (18)
C1—N1—C4—C3	−4.2 (2)	C3—O4—C14—O5	0.9 (4)
C5—N1—C4—C3	175.7 (2)	C3—O4—C14—C15	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.98	2.51	3.206 (2)	128
C3—H3···O1ii	0.98	2.55	3.276 (3)	131
C5—H5b···O6iii	0.97	2.49	3.328 (3)	144
C13—H13b···Cg1ii	0.96	2.95	3.702 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.98	2.51	3.206 (2)	128
C3—H3⋯O1ii	0.98	2.55	3.276 (3)	131
C5—H5b⋯O6iii	0.97	2.49	3.328 (3)	144
C13—H13b⋯Cg1ii	0.96	2.95	3.702 (3)	136

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C6–C11 ring.