3,4-Diethyl-2,5-dihydro-1H-pyrrole-2,5-dione

In the crystal structure of the title compound, C₈H₁₁NO₂, three distinct mol­ecules are present in the asymmetric unit. The mol­ecules are organized in two different hydrogen-bonded tapes, which form a complex layered structure. A structural comparison with the crystal structures of related maleimide derivatives unravels a stepwise evolution of morphological complexity with increasing mol­ecular complexity for this class of compounds.

Computing details

Data collection: EXPOSE in IPDS (Stoe & Cie, 1999); cell refinement: CELL in IPDS; data reduction: INTEGRATE in IPDS; program(s) used to solve structure: SIR92 (Giacovazzo, 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Version 1.4.1; Macrae et al., 2006); software used to prepare material for publication: publCIF.

3,4-Diethyl-2,5-dihydro-1H-pyrrole-2,5-dione

Crystal data

C8H11NO2	F(000) = 984
Mr = 153.18	Dx = 1.242 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 981 reflections
a = 7.9602 (13) Å	θ = 2.3–25.8°
b = 11.6135 (18) Å	µ = 0.09 mm^−1
c = 26.586 (5) Å	T = 193 K
V = 2457.7 (7) Å^3	Plate, colourless
Z = 12	0.41 × 0.19 × 0.05 mm

Data collection

Stoe IPDS-1 diffractometer	2593 independent reflections
Radiation source: fine-focus sealed tube	1381 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
φ scans	θmax = 25.8°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→9
Tmin = 0.876, Tmax = 0.998	k = −14→12
8425 measured reflections	l = −32→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 0.80	w = 1/[σ^2(Fo^2) + (0.0488P)^2] where P = (Fo^2 + 2Fc^2)/3
2593 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.23 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
C1	0.4429 (5)	0.6386 (4)	0.9964 (2)	0.0276 (12)
C2	0.3457 (4)	0.5275 (4)	0.9917 (2)	0.0275 (12)
C3	0.1592 (5)	0.5274 (5)	0.9852 (2)	0.0363 (14)
H3A	0.1093	0.5845	1.0085	0.044*
H3B	0.1150	0.4506	0.9945	0.044*
C4	0.1054 (6)	0.5555 (5)	0.9321 (2)	0.0519 (16)
H4A	0.1462	0.6323	0.9230	0.078*
H4B	−0.0175	0.5539	0.9300	0.078*
H4C	0.1526	0.4984	0.9089	0.078*
C5	0.4551 (5)	0.4416 (4)	0.9932 (2)	0.0275 (12)
C6	0.4313 (6)	0.3157 (4)	0.9880 (2)	0.0306 (13)
H6A	0.3103	0.2973	0.9911	0.037*
H6B	0.4914	0.2760	1.0156	0.037*
C7	0.4965 (6)	0.2709 (5)	0.9374 (3)	0.0439 (15)
H7A	0.4406	0.3123	0.9099	0.066*
H7B	0.4724	0.1884	0.9345	0.066*
H7C	0.6180	0.2834	0.9353	0.066*
C8	0.6293 (4)	0.4915 (4)	1.0004 (2)	0.0254 (12)
C9	0.5884 (5)	0.1324 (4)	0.8085 (2)	0.0253 (11)
C10	0.4158 (5)	0.0843 (4)	0.8160 (2)	0.0250 (11)
C11	0.3877 (5)	−0.0404 (4)	0.8248 (2)	0.0330 (13)
H11A	0.4563	−0.0852	0.8007	0.040*
H11B	0.2681	−0.0588	0.8185	0.040*
C12	0.4338 (7)	−0.0760 (5)	0.8784 (3)	0.0474 (16)
H12A	0.5517	−0.0567	0.8850	0.071*
H12B	0.4176	−0.1592	0.8823	0.071*
H12C	0.3618	−0.0350	0.9023	0.071*
C13	0.3059 (5)	0.1708 (4)	0.8135 (2)	0.0236 (12)
C14	0.1192 (5)	0.1744 (4)	0.8203 (2)	0.0273 (12)
H14A	0.0718	0.0980	0.8120	0.033*
H14B	0.0709	0.2311	0.7966	0.033*
C15	0.0687 (6)	0.2062 (5)	0.8730 (2)	0.0457 (16)
H15A	0.1174	0.1510	0.8967	0.069*
H15B	−0.0540	0.2047	0.8758	0.069*
H15C	0.1098	0.2837	0.8808	0.069*
C16	0.4034 (5)	0.2799 (4)	0.8023 (2)	0.0255 (12)
C17	0.9042 (5)	0.5044 (4)	0.7996 (2)	0.0257 (11)
C18	0.8084 (5)	0.6124 (4)	0.8091 (2)	0.0218 (11)
C19	0.6211 (5)	0.6108 (4)	0.8159 (2)	0.0319 (13)
H19A	0.5708	0.5541	0.7926	0.038*
H19B	0.5745	0.6876	0.8078	0.038*
C20	0.5754 (6)	0.5791 (5)	0.8700 (2)	0.0477 (16)
H20A	0.6227	0.5035	0.8782	0.072*
H20B	0.4529	0.5765	0.8735	0.072*
H20C	0.6214	0.6371	0.8930	0.072*
C21	0.9170 (5)	0.6993 (4)	0.8110 (2)	0.0246 (11)
C22	0.8900 (6)	0.8249 (4)	0.8195 (2)	0.0321 (13)
H22A	0.7720	0.8444	0.8114	0.039*
H22B	0.9634	0.8690	0.7964	0.039*
C23	0.9275 (6)	0.8609 (4)	0.8737 (2)	0.0402 (14)
H23A	0.8547	0.8178	0.8967	0.060*
H23B	0.9065	0.9435	0.8776	0.060*
H23C	1.0454	0.8443	0.8815	0.060*
C24	1.0920 (5)	0.6508 (4)	0.8044 (2)	0.0247 (11)
N1	0.6102 (4)	0.6101 (3)	1.00200 (18)	0.0295 (10)
H1	0.6925	0.6598	1.0060	0.035*
N2	0.5713 (4)	0.2488 (3)	0.80102 (17)	0.0268 (10)
H2	0.6552	0.2969	0.7961	0.032*
N3	1.0725 (3)	0.5341 (3)	0.79766 (17)	0.0253 (10)
H3	1.1553	0.4852	0.7928	0.030*
O1	0.3882 (4)	0.7353 (3)	0.99506 (16)	0.0383 (9)
O2	0.7597 (3)	0.4410 (3)	1.00397 (17)	0.0389 (10)
O3	0.7199 (3)	0.0798 (3)	0.80870 (17)	0.0372 (10)
O4	0.3499 (3)	0.3761 (3)	0.79650 (17)	0.0369 (11)
O5	0.8515 (3)	0.4078 (3)	0.79391 (16)	0.0359 (10)
O6	1.2237 (3)	0.7029 (3)	0.80527 (16)	0.0359 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.021 (2)	0.035 (3)	0.027 (4)	0.001 (2)	−0.003 (2)	−0.004 (2)
C2	0.0218 (18)	0.029 (2)	0.032 (4)	−0.0019 (18)	0.0001 (18)	0.002 (2)
C3	0.0216 (19)	0.043 (3)	0.044 (4)	0.0001 (19)	0.003 (2)	0.012 (3)
C4	0.031 (2)	0.075 (4)	0.050 (5)	0.002 (3)	−0.005 (2)	0.005 (3)
C5	0.027 (2)	0.028 (3)	0.028 (4)	−0.0022 (18)	−0.003 (2)	0.003 (2)
C6	0.032 (2)	0.021 (2)	0.038 (4)	−0.0034 (19)	−0.004 (2)	0.006 (2)
C7	0.054 (3)	0.031 (3)	0.047 (5)	−0.008 (2)	−0.005 (3)	−0.009 (3)
C8	0.0173 (18)	0.026 (3)	0.033 (4)	−0.0015 (17)	0.000 (2)	0.002 (2)
C9	0.018 (2)	0.021 (2)	0.037 (4)	0.0041 (18)	−0.001 (2)	−0.002 (2)
C10	0.023 (2)	0.027 (3)	0.025 (3)	−0.0040 (19)	−0.004 (2)	−0.003 (2)
C11	0.030 (2)	0.021 (3)	0.048 (4)	0.001 (2)	0.007 (2)	−0.003 (2)
C12	0.051 (3)	0.035 (3)	0.056 (5)	0.006 (2)	0.009 (3)	0.015 (3)
C13	0.019 (2)	0.024 (3)	0.028 (4)	0.0001 (18)	0.000 (2)	−0.004 (2)
C14	0.016 (2)	0.034 (3)	0.031 (4)	−0.0006 (18)	0.004 (2)	−0.004 (2)
C15	0.024 (3)	0.071 (4)	0.042 (4)	−0.001 (3)	0.009 (2)	−0.008 (3)
C16	0.020 (2)	0.029 (3)	0.028 (4)	0.0003 (19)	−0.002 (2)	0.001 (2)
C17	0.024 (2)	0.026 (3)	0.027 (3)	−0.0037 (19)	0.002 (2)	0.001 (2)
C18	0.0179 (19)	0.025 (3)	0.023 (3)	0.0010 (17)	−0.0003 (18)	0.002 (2)
C19	0.017 (2)	0.044 (3)	0.034 (4)	0.002 (2)	0.005 (2)	0.007 (3)
C20	0.031 (3)	0.066 (4)	0.046 (5)	0.005 (2)	0.012 (3)	0.013 (3)
C21	0.024 (2)	0.021 (2)	0.029 (3)	0.0026 (17)	0.000 (2)	0.003 (2)
C22	0.030 (2)	0.018 (2)	0.048 (4)	0.0036 (19)	0.002 (2)	0.004 (2)
C23	0.044 (3)	0.030 (3)	0.046 (4)	0.005 (2)	−0.002 (3)	−0.009 (3)
C24	0.021 (2)	0.027 (3)	0.026 (3)	−0.0011 (19)	0.001 (2)	−0.003 (2)
N1	0.0210 (16)	0.022 (2)	0.046 (3)	−0.0003 (15)	−0.0019 (18)	−0.005 (2)
N2	0.0156 (16)	0.023 (2)	0.042 (3)	−0.0050 (14)	0.0031 (18)	−0.0020 (19)
N3	0.0129 (15)	0.022 (2)	0.041 (3)	0.0048 (15)	0.0059 (17)	−0.0020 (19)
O1	0.0352 (17)	0.0239 (19)	0.056 (3)	0.0055 (15)	−0.0009 (19)	0.0041 (19)
O2	0.0260 (15)	0.0318 (19)	0.059 (3)	0.0019 (13)	−0.0061 (16)	−0.0032 (19)
O3	0.0250 (15)	0.0285 (19)	0.058 (3)	0.0069 (13)	0.0030 (17)	0.0007 (19)
O4	0.0292 (16)	0.0213 (19)	0.060 (3)	0.0078 (13)	0.0034 (16)	0.0011 (18)
O5	0.0268 (16)	0.0221 (19)	0.059 (3)	−0.0033 (14)	0.0055 (15)	−0.0045 (18)
O6	0.0164 (15)	0.0277 (18)	0.064 (3)	−0.0042 (12)	0.0026 (17)	−0.0018 (19)

Geometric parameters (Å, º)

C1—O1	1.205 (6)	C13—C16	1.515 (6)
C1—N1	1.380 (5)	C14—C15	1.504 (7)
C1—C2	1.509 (6)	C14—H14A	0.9900
C2—C5	1.324 (6)	C14—H14B	0.9900
C2—C3	1.494 (5)	C15—H15A	0.9800
C3—C4	1.511 (8)	C15—H15B	0.9800
C3—H3A	0.9900	C15—H15C	0.9800
C3—H3B	0.9900	C16—O4	1.205 (5)
C4—H4A	0.9800	C16—N2	1.385 (5)
C4—H4B	0.9800	C17—O5	1.208 (5)
C4—H4C	0.9800	C17—N3	1.384 (5)
C5—C6	1.481 (6)	C17—C18	1.490 (6)
C5—C8	1.516 (5)	C18—C21	1.330 (6)
C6—C7	1.533 (8)	C18—C19	1.503 (5)
C6—H6A	0.9900	C19—C20	1.527 (8)
C6—H6B	0.9900	C19—H19A	0.9900
C7—H7A	0.9800	C19—H19B	0.9900
C7—H7B	0.9800	C20—H20A	0.9800
C7—H7C	0.9800	C20—H20B	0.9800
C8—O2	1.196 (5)	C20—H20C	0.9800
C8—N1	1.386 (5)	C21—C22	1.492 (6)
C9—O3	1.212 (5)	C21—C24	1.513 (6)
C9—N2	1.374 (6)	C22—C23	1.529 (8)
C9—C10	1.496 (6)	C22—H22A	0.9900
C10—C13	1.334 (6)	C22—H22B	0.9900
C10—C11	1.483 (6)	C23—H23A	0.9800
C11—C12	1.529 (8)	C23—H23B	0.9800
C11—H11A	0.9900	C23—H23C	0.9800
C11—H11B	0.9900	C24—O6	1.211 (5)
C12—H12A	0.9800	C24—N3	1.376 (6)
C12—H12B	0.9800	N1—H1	0.8800
C12—H12C	0.9800	N2—H2	0.8800
C13—C14	1.498 (5)	N3—H3	0.8800
O1—C1—N1	125.1 (4)	C15—C14—H14A	109.1
O1—C1—C2	127.5 (4)	C13—C14—H14B	109.1
N1—C1—C2	107.4 (4)	C15—C14—H14B	109.1
C5—C2—C3	131.0 (4)	H14A—C14—H14B	107.8
C5—C2—C1	107.7 (3)	C14—C15—H15A	109.5
C3—C2—C1	121.3 (4)	C14—C15—H15B	109.5
C2—C3—C4	112.9 (4)	H15A—C15—H15B	109.5
C2—C3—H3A	109.0	C14—C15—H15C	109.5
C4—C3—H3A	109.0	H15A—C15—H15C	109.5
C2—C3—H3B	109.0	H15B—C15—H15C	109.5
C4—C3—H3B	109.0	O4—C16—N2	125.4 (4)
H3A—C3—H3B	107.8	O4—C16—C13	128.2 (4)
C3—C4—H4A	109.5	N2—C16—C13	106.3 (4)
C3—C4—H4B	109.5	O5—C17—N3	124.3 (4)
H4A—C4—H4B	109.5	O5—C17—C18	128.8 (4)
C3—C4—H4C	109.5	N3—C17—C18	107.0 (4)
H4A—C4—H4C	109.5	C21—C18—C17	108.2 (3)
H4B—C4—H4C	109.5	C21—C18—C19	130.5 (4)
C2—C5—C6	131.1 (4)	C17—C18—C19	121.2 (4)
C2—C5—C8	108.5 (4)	C18—C19—C20	110.6 (4)
C6—C5—C8	120.4 (4)	C18—C19—H19A	109.5
C5—C6—C7	112.0 (5)	C20—C19—H19A	109.5
C5—C6—H6A	109.2	C18—C19—H19B	109.5
C7—C6—H6A	109.2	C20—C19—H19B	109.5
C5—C6—H6B	109.2	H19A—C19—H19B	108.1
C7—C6—H6B	109.2	C19—C20—H20A	109.5
H6A—C6—H6B	107.9	C19—C20—H20B	109.5
C6—C7—H7A	109.5	H20A—C20—H20B	109.5
C6—C7—H7B	109.5	C19—C20—H20C	109.5
H7A—C7—H7B	109.5	H20A—C20—H20C	109.5
C6—C7—H7C	109.5	H20B—C20—H20C	109.5
H7A—C7—H7C	109.5	C18—C21—C22	130.9 (4)
H7B—C7—H7C	109.5	C18—C21—C24	108.2 (4)
O2—C8—N1	125.5 (4)	C22—C21—C24	120.9 (4)
O2—C8—C5	128.0 (4)	C21—C22—C23	112.4 (4)
N1—C8—C5	106.4 (3)	C21—C22—H22A	109.1
O3—C9—N2	125.6 (4)	C23—C22—H22A	109.1
O3—C9—C10	127.2 (4)	C21—C22—H22B	109.1
N2—C9—C10	107.2 (3)	C23—C22—H22B	109.1
C13—C10—C11	130.1 (4)	H22A—C22—H22B	107.9
C13—C10—C9	108.3 (4)	C22—C23—H23A	109.5
C11—C10—C9	121.6 (4)	C22—C23—H23B	109.5
C10—C11—C12	112.0 (5)	H23A—C23—H23B	109.5
C10—C11—H11A	109.2	C22—C23—H23C	109.5
C12—C11—H11A	109.2	H23A—C23—H23C	109.5
C10—C11—H11B	109.2	H23B—C23—H23C	109.5
C12—C11—H11B	109.2	O6—C24—N3	126.4 (4)
H11A—C11—H11B	107.9	O6—C24—C21	127.5 (4)
C11—C12—H12A	109.5	N3—C24—C21	106.1 (3)
C11—C12—H12B	109.5	C1—N1—C8	109.9 (3)
H12A—C12—H12B	109.5	C1—N1—H1	125.0
C11—C12—H12C	109.5	C8—N1—H1	125.0
H12A—C12—H12C	109.5	C9—N2—C16	110.4 (3)
H12B—C12—H12C	109.5	C9—N2—H2	124.8
C10—C13—C14	131.7 (4)	C16—N2—H2	124.8
C10—C13—C16	107.7 (4)	C24—N3—C17	110.5 (3)
C14—C13—C16	120.6 (4)	C24—N3—H3	124.8
C13—C14—C15	112.7 (4)	C17—N3—H3	124.8
C13—C14—H14A	109.1
O1—C1—C2—C5	177.5 (6)	C10—C13—C16—N2	−2.5 (5)
N1—C1—C2—C5	−1.7 (6)	C14—C13—C16—N2	176.6 (4)
O1—C1—C2—C3	−0.9 (9)	O5—C17—C18—C21	−177.7 (6)
N1—C1—C2—C3	179.9 (5)	N3—C17—C18—C21	1.7 (5)
C5—C2—C3—C4	−100.0 (7)	O5—C17—C18—C19	3.6 (8)
C1—C2—C3—C4	77.9 (7)	N3—C17—C18—C19	−177.0 (4)
C3—C2—C5—C6	1.3 (11)	C21—C18—C19—C20	−95.8 (7)
C1—C2—C5—C6	−176.9 (6)	C17—C18—C19—C20	82.6 (6)
C3—C2—C5—C8	179.8 (5)	C17—C18—C21—C22	180.0 (6)
C1—C2—C5—C8	1.6 (6)	C19—C18—C21—C22	−1.5 (10)
C2—C5—C6—C7	107.1 (7)	C17—C18—C21—C24	−1.8 (5)
C8—C5—C6—C7	−71.2 (6)	C19—C18—C21—C24	176.8 (5)
C2—C5—C8—O2	179.3 (6)	C18—C21—C22—C23	100.0 (7)
C6—C5—C8—O2	−2.0 (9)	C24—C21—C22—C23	−78.1 (6)
C2—C5—C8—N1	−1.0 (6)	C18—C21—C24—O6	−178.0 (5)
C6—C5—C8—N1	177.7 (5)	C22—C21—C24—O6	0.5 (8)
O3—C9—C10—C13	179.5 (5)	C18—C21—C24—N3	1.3 (6)
N2—C9—C10—C13	−0.8 (6)	C22—C21—C24—N3	179.8 (5)
O3—C9—C10—C11	−0.1 (8)	O1—C1—N1—C8	−178.2 (6)
N2—C9—C10—C11	179.5 (5)	C2—C1—N1—C8	1.1 (6)
C13—C10—C11—C12	−103.6 (6)	O2—C8—N1—C1	179.6 (5)
C9—C10—C11—C12	76.0 (6)	C5—C8—N1—C1	−0.1 (6)
C11—C10—C13—C14	2.7 (10)	O3—C9—N2—C16	178.8 (5)
C9—C10—C13—C14	−177.0 (5)	C10—C9—N2—C16	−0.8 (6)
C11—C10—C13—C16	−178.4 (6)	O4—C16—N2—C9	−179.5 (6)
C9—C10—C13—C16	2.0 (6)	C13—C16—N2—C9	2.0 (5)
C10—C13—C14—C15	94.7 (7)	O6—C24—N3—C17	179.1 (5)
C16—C13—C14—C15	−84.1 (6)	C21—C24—N3—C17	−0.2 (6)
C10—C13—C16—O4	179.1 (6)	O5—C17—N3—C24	178.6 (5)
C14—C13—C16—O4	−1.8 (9)	C18—C17—N3—C24	−0.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.88	1.98	2.851 (4)	172
N2—H2···O5	0.88	2.03	2.901 (4)	173
N3—H3···O4^ii	0.88	2.00	2.872 (4)	169

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