N,N'-Ethyl­enedisuccin­imide

The title compound, C₁₀H₁₂N₂O₄, crystallizes as discrete mol­ecules disposed about crystallographic centres of symmetry, with two independent half-mol­ecules constituting the asymmetric unit of the unit cell. The succin­imide rings are essentially planar. No unusual features are observed in the molecular geometry.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.137
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).

N,N'-ethylenedisuccinimide

Crystal data

C10H12N2O4	F(000) = 472
Mr = 224.22	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.5653 (13) Å	θ = 8.3–10.6°
b = 8.3613 (10) Å	µ = 0.11 mm^−1
c = 9.9285 (15) Å	T = 295 K
β = 90.694 (10)°	Prismatic, colorless
V = 1043.0 (2) Å^3	0.50 × 0.40 × 0.30 mm
Z = 4

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.031
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.9°
Graphite monochromator	h = −7→16
ω–2θ scans	k = 0→10
2655 measured reflections	l = −12→12
2396 independent reflections	3 standard reflections every 150 reflections
1825 reflections with I > 2σ(I)	intensity decay: 1.2%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0858P)^2 + 0.1556P] where P = (Fo^2 + 2Fc^2)/3
2396 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. The scan width was (1.70 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

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

	x	y	z	Uiso*/Ueq
O21	0.27827 (8)	−0.14811 (15)	0.44453 (11)	0.0479 (4)
O51	0.51818 (10)	0.14448 (18)	0.21134 (13)	0.0623 (5)
N1	0.40577 (9)	0.01381 (14)	0.35400 (11)	0.0326 (3)
C11	0.45740 (11)	0.05978 (17)	0.47970 (14)	0.0364 (4)
C21	0.31874 (10)	−0.08840 (17)	0.34728 (14)	0.0334 (4)
C31	0.28656 (12)	−0.1055 (2)	0.20148 (15)	0.0435 (5)
C41	0.36857 (13)	−0.0112 (2)	0.12343 (15)	0.0431 (4)
C51	0.44123 (11)	0.06040 (19)	0.22852 (15)	0.0378 (4)
O22	0.21295 (8)	0.30734 (14)	0.06096 (11)	0.0472 (3)
O52	−0.03527 (9)	0.57812 (17)	0.29858 (13)	0.0599 (5)
N2	0.07448 (9)	0.44313 (14)	0.15613 (11)	0.0342 (3)
C12	−0.00104 (11)	0.42676 (18)	0.04488 (15)	0.0389 (4)
C22	0.17597 (10)	0.37805 (16)	0.15513 (14)	0.0337 (4)
C32	0.22731 (12)	0.4122 (2)	0.29009 (16)	0.0449 (5)
C42	0.14505 (13)	0.50345 (19)	0.36953 (15)	0.0424 (4)
C52	0.04993 (11)	0.51648 (18)	0.27671 (14)	0.0376 (4)
H11A	0.49360	0.15860	0.46790	0.0440*
H11B	0.40530	0.07190	0.54760	0.0440*
H31A	0.28740	−0.21490	0.17540	0.0520*
H31B	0.21730	−0.06290	0.18650	0.0520*
H41A	0.40720	−0.07990	0.06550	0.0520*
H41B	0.33500	0.07040	0.07170	0.0520*
H12A	−0.07030	0.40970	0.07940	0.0470*
H12B	0.01860	0.33820	−0.00940	0.0470*
H32A	0.28960	0.47510	0.27920	0.0540*
H32B	0.24540	0.31520	0.33450	0.0540*
H42A	0.17090	0.60670	0.39290	0.0510*
H42B	0.12730	0.44680	0.44910	0.0510*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O21	0.0437 (6)	0.0538 (7)	0.0461 (6)	−0.0098 (5)	0.0021 (5)	0.0039 (5)
O51	0.0515 (7)	0.0746 (9)	0.0607 (8)	−0.0214 (7)	−0.0013 (6)	0.0183 (7)
N1	0.0297 (5)	0.0358 (6)	0.0321 (6)	−0.0017 (4)	−0.0067 (4)	−0.0010 (5)
C11	0.0341 (7)	0.0399 (7)	0.0349 (7)	0.0011 (6)	−0.0093 (5)	−0.0073 (6)
C21	0.0277 (6)	0.0348 (7)	0.0376 (7)	0.0015 (5)	−0.0051 (5)	−0.0014 (5)
C31	0.0376 (7)	0.0536 (9)	0.0389 (8)	−0.0024 (7)	−0.0125 (6)	−0.0059 (7)
C41	0.0471 (8)	0.0491 (8)	0.0330 (7)	0.0063 (7)	−0.0071 (6)	0.0021 (6)
C51	0.0343 (7)	0.0407 (7)	0.0382 (7)	0.0022 (6)	−0.0041 (6)	0.0072 (6)
O22	0.0414 (6)	0.0504 (6)	0.0498 (6)	0.0032 (5)	0.0060 (5)	−0.0085 (5)
O52	0.0443 (7)	0.0713 (9)	0.0641 (8)	0.0138 (6)	0.0029 (6)	−0.0178 (7)
N2	0.0311 (6)	0.0378 (6)	0.0336 (6)	0.0026 (5)	−0.0058 (4)	−0.0021 (5)
C12	0.0343 (7)	0.0410 (8)	0.0413 (8)	−0.0027 (6)	−0.0090 (6)	−0.0002 (6)
C22	0.0304 (6)	0.0330 (7)	0.0378 (7)	−0.0005 (5)	−0.0006 (5)	0.0032 (5)
C32	0.0369 (7)	0.0563 (9)	0.0413 (8)	0.0039 (7)	−0.0099 (6)	0.0035 (7)
C42	0.0470 (8)	0.0450 (8)	0.0351 (7)	−0.0028 (7)	−0.0062 (6)	−0.0023 (6)
C52	0.0390 (8)	0.0360 (7)	0.0379 (7)	0.0004 (6)	0.0010 (6)	−0.0028 (6)

Geometric parameters (Å, º)

O21—C21	1.2050 (18)	C11—H11B	0.9500
O51—C51	1.209 (2)	C31—H31B	0.9500
O22—C22	1.2042 (18)	C31—H31A	0.9500
O52—C52	1.2102 (19)	C41—H41B	0.9500
N1—C21	1.3889 (18)	C41—H41A	0.9500
N1—C51	1.3841 (19)	C12—C12^ii	1.515 (2)
N1—C11	1.4514 (18)	C22—C32	1.507 (2)
N2—C12	1.4539 (18)	C32—C42	1.514 (2)
N2—C52	1.3833 (18)	C42—C52	1.504 (2)
N2—C22	1.3866 (17)	C12—H12A	0.9500
C11—C11^i	1.516 (2)	C12—H12B	0.9500
C21—C31	1.505 (2)	C32—H32A	0.9500
C31—C41	1.518 (2)	C32—H32B	0.9500
C41—C51	1.503 (2)	C42—H42A	0.9500
C11—H11A	0.9500	C42—H42B	0.9500
O21···O22^iii	3.1861 (17)	C21···O51^x	3.091 (2)
O21···C22^iii	3.3449 (18)	C22···O21^v	3.3449 (18)
O21···C31^iv	3.280 (2)	C22···O52^viii	3.1057 (19)
O22···C11^v	3.3734 (18)	C31···O21^xii	3.280 (2)
O22···C32^v	3.263 (2)	C31···O51^x	3.330 (2)
O22···C42^v	3.325 (2)	C32···O22^iii	3.263 (2)
O22···C41	3.358 (2)	C41···O22	3.358 (2)
O22···O21^v	3.1861 (17)	C42···O22^iii	3.325 (2)
O51···C31^vi	3.330 (2)	C21···H11A^i	3.0300
O51···C21^vi	3.091 (2)	C32···H41B^iii	3.0900
O52···N2^vii	3.1249 (19)	C52···H12B^ii	3.0300
O52···C22^vii	3.1057 (19)	H11A···O51	2.5700
O52···C12^vii	3.332 (2)	H11A···C21^i	3.0300
O21···H11B	2.6300	H11A···H41A^vi	2.5400
O21···H12A^viii	2.6700	H11B···O21	2.6300
O21···H31A^iv	2.5600	H11B···O22^iii	2.6200
O21···H42A^ix	2.5000	H12A···O52	2.6200
O22···H12B	2.5400	H12A···O21^vii	2.6700
O22···H41B	2.5100	H12B···C52^ii	3.0300
O22···H11B^v	2.6200	H12B···O22	2.5400
O22···H32B^v	2.5100	H31A···O21^xii	2.5600
O22···H42B^v	2.6200	H31B···O52^viii	2.5800
O51···H11A	2.5700	H32A···O51^vi	2.8000
O51···H32A^x	2.8000	H32B···O22^iii	2.5100
O52···H12A	2.6200	H41A···H11A^x	2.5400
O52···H42B^xi	2.7800	H41B···C32^v	3.0900
O52···H31B^vii	2.5800	H41B···O22	2.5100
N2···O52^viii	3.1249 (19)	H42A···O21^xiii	2.5000
C11···O22^iii	3.3734 (18)	H42B···O52^xi	2.7800
C12···O52^viii	3.332 (2)	H42B···O22^iii	2.6200
C11—N1—C21	123.21 (11)	C51—C41—H41A	111.00
C11—N1—C51	123.64 (12)	C51—C41—H41B	111.00
C21—N1—C51	113.07 (11)	C31—C41—H41A	110.00
C12—N2—C52	123.29 (11)	N2—C12—C12^ii	110.79 (12)
C22—N2—C52	113.26 (11)	O22—C22—N2	124.18 (13)
C12—N2—C22	123.33 (11)	O22—C22—C32	128.18 (12)
N1—C11—C11^i	111.16 (11)	N2—C22—C32	107.64 (11)
O21—C21—N1	123.79 (13)	C22—C32—C42	105.73 (12)
O21—C21—C31	128.33 (13)	C32—C42—C52	105.05 (12)
N1—C21—C31	107.87 (12)	O52—C52—N2	123.45 (13)
C21—C31—C41	105.40 (12)	O52—C52—C42	128.24 (14)
C31—C41—C51	105.25 (12)	N2—C52—C42	108.31 (12)
O51—C51—N1	123.87 (14)	N2—C12—H12A	109.00
O51—C51—C41	127.87 (14)	N2—C12—H12B	109.00
N1—C51—C41	108.26 (12)	H12A—C12—H12B	109.00
C11^i—C11—H11A	106.00	C12^ii—C12—H12A	111.00
C11^i—C11—H11B	112.00	C12^ii—C12—H12B	107.00
N1—C11—H11A	109.00	C22—C32—H32A	110.00
N1—C11—H11B	109.00	C22—C32—H32B	110.00
H11A—C11—H11B	109.00	C42—C32—H32A	110.00
C21—C31—H31A	110.00	C42—C32—H32B	110.00
C21—C31—H31B	110.00	H32A—C32—H32B	109.00
C41—C31—H31A	111.00	C32—C42—H42A	111.00
C41—C31—H31B	111.00	C32—C42—H42B	111.00
H31A—C31—H31B	109.00	C52—C42—H42A	111.00
C31—C41—H41B	110.00	C52—C42—H42B	111.00
H41A—C41—H41B	109.00	H42A—C42—H42B	109.00
C21—N1—C11—C11^i	87.24 (15)	C22—N2—C52—O52	−178.74 (14)
C51—N1—C11—C11^i	−89.34 (16)	C22—N2—C52—C42	0.89 (16)
C11—N1—C21—O21	0.0 (2)	C52—N2—C22—C32	−0.64 (16)
C11—N1—C21—C31	179.10 (12)	C12—N2—C52—O52	−2.6 (2)
C51—N1—C21—O21	176.87 (14)	N1—C11—C11^i—N1^i	−180.00 (11)
C51—N1—C21—C31	−4.00 (16)	O21—C21—C31—C41	−177.28 (15)
C11—N1—C51—O51	−0.4 (2)	N1—C21—C31—C41	3.64 (16)
C11—N1—C51—C41	179.50 (12)	C21—C31—C41—C51	−2.09 (16)
C21—N1—C51—O51	−177.30 (15)	C31—C41—C51—O51	179.77 (17)
C21—N1—C51—C41	2.62 (17)	C31—C41—C51—N1	−0.14 (17)
C52—N2—C12—C12^ii	87.17 (16)	N2—C12—C12^ii—N2^ii	−179.98 (14)
C12—N2—C22—O22	3.0 (2)	O22—C22—C32—C42	−179.64 (15)
C22—N2—C12—C12^ii	−97.03 (15)	N2—C22—C32—C42	0.12 (15)
C12—N2—C52—C42	177.08 (12)	C22—C32—C42—C52	0.37 (16)
C12—N2—C22—C32	−176.83 (12)	C32—C42—C52—O52	178.86 (16)
C52—N2—C22—O22	179.13 (14)	C32—C42—C52—N2	−0.75 (16)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z; (iii) x, −y+1/2, z+1/2; (iv) x, −y−1/2, z+1/2; (v) x, −y+1/2, z−1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) −x, y+1/2, −z+1/2; (viii) −x, y−1/2, −z+1/2; (ix) x, y−1, z; (x) −x+1, y−1/2, −z+1/2; (xi) −x, −y+1, −z+1; (xii) x, −y−1/2, z−1/2; (xiii) x, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O22	0.95	2.54	2.8709 (18)	100
C31—H31A···O21^xii	0.95	2.56	3.280 (2)	132
C31—H31B···O52^viii	0.95	2.58	3.511 (2)	167
C32—H32B···O22^iii	0.95	2.51	3.263 (2)	136
C41—H41B···O22	0.95	2.51	3.358 (2)	149
C42—H42A···O21^xiii	0.95	2.50	3.437 (2)	167

Symmetry codes: (iii) x, −y+1/2, z+1/2; (viii) −x, y−1/2, −z+1/2; (xii) x, −y−1/2, z−1/2; (xiii) x, y+1, z.