Bis(ethano-laminium) succinate-succinic acid (1/1).

The asymmetric unit of the title compound, 2C(2)H(8)NO(+)·C(4)H(4)O(4) (2-)·C(4)H(6)O(4), consists of half a succinate anion, half a succinic acid mol-ecule and one ethano-laminium cation. The succinate anion and succinic acid mol-ecule, both of which are located on inversion centres, are linked by O-H⋯O hydrogen bonds, forming a chain along the [2[Formula: see text]0] direction. The chain and the ethano-laminium cation are further connected by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related structures of co-crystals and salts of succinic acid, see: Aakeroy et al. (1998 ▶); Batchelor et al. (2001 ▶); Borthwick (1980 ▶); Braga et al. (2003 ▶); Bruno et al. (2004 ▶); Büyükgüngör & Odabasoglu (2002 ▶); Flensburg et al. (1995 ▶); Kuipers et al. (1997 ▶); Li et al. (2003 ▶); MacDonald et al. (2001 ▶); Prasad & Vijayan (1990 ▶); Reitz et al. (1998 ▶); Urbanczyk-Lipkowska (2000 ▶).

Experimental

Crystal data

2C2H8NO+·C4H4O4 2−·C4H6O4

M = 358.35

Triclinic,

a = 5.821 (5) Å

b = 8.428 (7) Å

c = 9.077 (7) Å

α = 87.74 (1)°

β = 73.628 (11)°

γ = 80.380 (12)°

V = 421.2 (6) Å3

Z = 1

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.42 × 0.34 × 0.30 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.855, T max = 0.898

2330 measured reflections

1628 independent reflections

1517 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.106

S = 1.07

1628 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034428/is2756sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034428/is2756Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034428/is2756Isup3.cml

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

2C2H8NO+·C4H4O42−·C4H6O4	Z = 1
Mr = 358.35	F(000) = 192.0
Triclinic, P1	Dx = 1.413 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.821 (5) Å	Cell parameters from 1360 reflections
b = 8.428 (7) Å	θ = 2.1–17.8°
c = 9.077 (7) Å	µ = 0.12 mm−1
α = 87.74 (1)°	T = 293 K
β = 73.628 (11)°	Prism, colorless
γ = 80.380 (12)°	0.42 × 0.34 × 0.30 mm
V = 421.2 (6) Å3

Bruker APEX area-detector diffractometer	1628 independent reflections
Radiation source: fine-focus sealed tube	1517 reflections with I > 2σ(I)
graphite	Rint = 0.011
φ and ω scan	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −4→7
Tmin = 0.855, Tmax = 0.898	k = −9→10
2330 measured reflections	l = −11→10

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) = 0.106	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1261P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1628 reflections	Δρmax = 0.37 e Å−3
110 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.160 (15)

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	0.27229 (18)	0.92694 (13)	0.23761 (10)	0.0366 (3)
O2	0.49374 (19)	0.79510 (15)	0.37464 (11)	0.0455 (3)
H2	0.4875	0.7808	0.4655	0.068*
O3	0.7920 (2)	0.61078 (13)	0.76185 (11)	0.0410 (3)
O4	0.54895 (19)	0.74043 (13)	0.63248 (11)	0.0401 (3)
O5	0.24811 (17)	0.85165 (11)	0.90544 (11)	0.0341 (3)
H5	0.3825	0.8324	0.8434	0.051*
N1	−0.25612 (19)	0.82179 (14)	1.00467 (12)	0.0293 (3)
H1A	−0.4002	0.8428	1.0740	0.044*
H1B	−0.2650	0.7570	0.9321	0.044*
H1C	−0.2131	0.9133	0.9624	0.044*
C1	0.2989 (2)	0.89023 (16)	0.36369 (14)	0.0263 (3)
C2	0.1142 (2)	0.95017 (16)	0.51200 (14)	0.0275 (3)
H2A	0.1871	1.0147	0.5668	0.033*
H2B	0.0709	0.8586	0.5756	0.033*
C3	0.7343 (2)	0.63837 (16)	0.64176 (14)	0.0275 (3)
C4	0.8844 (2)	0.55193 (17)	0.49388 (15)	0.0328 (3)
H4A	0.7865	0.4850	0.4619	0.039*
H4B	0.9250	0.6314	0.4146	0.039*
C5	0.1738 (2)	0.70523 (16)	0.96716 (17)	0.0336 (3)
H5A	0.2895	0.6486	1.0177	0.040*
H5B	0.1672	0.6370	0.8854	0.040*
C6	−0.0726 (2)	0.74220 (17)	1.08064 (15)	0.0301 (3)
H6A	−0.1207	0.6431	1.1278	0.036*
H6B	−0.0653	0.8120	1.1610	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0321 (5)	0.0531 (7)	0.0204 (5)	0.0042 (4)	−0.0067 (4)	0.0002 (4)
O2	0.0322 (6)	0.0685 (8)	0.0230 (5)	0.0212 (5)	−0.0038 (4)	−0.0017 (5)
O3	0.0455 (6)	0.0490 (6)	0.0238 (5)	0.0142 (5)	−0.0135 (4)	−0.0085 (4)
O4	0.0341 (6)	0.0510 (6)	0.0240 (5)	0.0185 (5)	−0.0041 (4)	−0.0040 (4)
O5	0.0315 (5)	0.0336 (5)	0.0291 (5)	−0.0030 (4)	0.0042 (4)	−0.0051 (4)
N1	0.0265 (6)	0.0322 (6)	0.0259 (6)	−0.0004 (4)	−0.0040 (4)	−0.0022 (4)
C1	0.0226 (6)	0.0327 (7)	0.0218 (6)	−0.0008 (5)	−0.0052 (5)	−0.0003 (5)
C2	0.0227 (7)	0.0359 (7)	0.0204 (6)	0.0027 (5)	−0.0047 (5)	0.0002 (5)
C3	0.0268 (6)	0.0303 (7)	0.0221 (6)	0.0030 (5)	−0.0057 (5)	−0.0021 (5)
C4	0.0305 (7)	0.0401 (8)	0.0240 (7)	0.0103 (6)	−0.0096 (6)	−0.0077 (6)
C5	0.0284 (7)	0.0299 (7)	0.0387 (8)	0.0014 (5)	−0.0066 (6)	−0.0008 (6)
C6	0.0296 (7)	0.0349 (7)	0.0250 (6)	−0.0038 (5)	−0.0075 (5)	0.0030 (5)

O1—C1	1.2187 (18)	C2—C2i	1.516 (2)
O2—C1	1.3009 (18)	C2—H2A	0.9700
O2—H2	0.8200	C2—H2B	0.9700
O3—C3	1.2310 (18)	C3—C4	1.5162 (19)
O4—C3	1.2831 (17)	C4—C4ii	1.508 (3)
O5—C5	1.4181 (19)	C4—H4A	0.9700
O5—H5	0.8200	C4—H4B	0.9700
N1—C6	1.4851 (18)	C5—C6	1.503 (2)
N1—H1A	0.8900	C5—H5A	0.9700
N1—H1B	0.8900	C5—H5B	0.9700
N1—H1C	0.8900	C6—H6A	0.9700
C1—C2	1.5097 (19)	C6—H6B	0.9700
C1—O2—H2	109.5	O4—C3—C4	116.06 (11)
C5—O5—H5	109.5	C4ii—C4—C3	114.11 (14)
C6—N1—H1A	109.5	C4ii—C4—H4A	108.7
C6—N1—H1B	109.5	C3—C4—H4A	108.7
H1A—N1—H1B	109.5	C4ii—C4—H4B	108.7
C6—N1—H1C	109.5	C3—C4—H4B	108.7
H1A—N1—H1C	109.5	H4A—C4—H4B	107.6
H1B—N1—H1C	109.5	O5—C5—C6	108.92 (11)
O1—C1—O2	119.92 (12)	O5—C5—H5A	109.9
O1—C1—C2	123.11 (12)	C6—C5—H5A	109.9
O2—C1—C2	116.97 (11)	O5—C5—H5B	109.9
C1—C2—C2i	113.14 (13)	C6—C5—H5B	109.9
C1—C2—H2A	109.0	H5A—C5—H5B	108.3
C2i—C2—H2A	109.0	N1—C6—C5	111.06 (12)
C1—C2—H2B	109.0	N1—C6—H6A	109.4
C2i—C2—H2B	109.0	C5—C6—H6A	109.4
H2A—C2—H2B	107.8	N1—C6—H6B	109.4
O3—C3—O4	123.24 (12)	C5—C6—H6B	109.4
O3—C3—C4	120.70 (12)	H6A—C6—H6B	108.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1iii	0.89	2.09	2.976 (2)	171
N1—H1B···O3iv	0.89	1.93	2.810 (2)	167
N1—H1C···O5	0.89	2.55	2.868 (3)	102
N1—H1C···O5v	0.89	2.31	2.913 (3)	125
O2—H2···O4	0.82	1.66	2.466 (2)	166
O5—H5···O4	0.82	2.01	2.697 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.89	2.09	2.976 (2)	171
N1—H1B⋯O3ii	0.89	1.93	2.810 (2)	167
N1—H1C⋯O5	0.89	2.55	2.868 (3)	102
N1—H1C⋯O5iii	0.89	2.31	2.913 (3)	125
O2—H2⋯O4	0.82	1.66	2.466 (2)	166
O5—H5⋯O4	0.82	2.01	2.697 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) .