Bis(ethano­laminium) succinate–succinic acid (1/1)

Zhang, M.; Wang, C.; Fan, Z.

doi:10.1107/S1600536811034428

organic compounds

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Volume 67| Part 9| September 2011| Page o2504

doi:10.1107/S1600536811034428

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Bis(ethanolaminium) succinate–succinic acid (1/1)

Miao Zhang,^a Cong Wang ^a and Zheng Fan ^b ^*

^aCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bCollege of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: fzt713@163.com

(Received 22 July 2011; accepted 22 August 2011; online 27 August 2011)

The asymmetric unit of the title compound, 2C₂H₈NO⁺·C₄H₄O₄²⁻·C₄H₆O₄, consists of half a succinate anion, half a succinic acid molecule and one ethanolaminium cation. The succinate anion and succinic acid molecule, both of which are located on inversion centres, are linked by O—H⋯O hydrogen bonds, forming a chain along the [2 $[\overline{1}]$ 0] direction. The chain and the ethanolaminium 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⁺·C₄H₄O₄²⁻·C₄H₆O₄
M_r = 358.35
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.106
S = 1.07
1628 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) x-1, y, z+1; (ii) x-1, y, z; (iii) -x, -y+2, -z+2.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034428/is2756sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811034428/is2756Isup3.cml

checkCIF report

Comment top

There exist three forms of succinic acid in molecular complex, namely, succinate (Kuipers et al., 1997; Urbanczyk-Lipkowska, 2000), succinic acid (Aakeroy et al., 1998; Batchelor et al., 2001), hydrogen succinate (Flensburg et al., 1995; MacDonald et al., 2001). Interestingly, some mixed forms are also available (Prasad & Vijayan, 1990; Reitz et al., 1998; Büyükgüngör & Odabasoglu, 2002; Braga et al., 2003; Bruno et al., 2004). However, no convincing explanation for the formation of any of the complex. Recently, the title complex, (I) (Table 1 & Fig. 1), is synthesized, and the structure is studied hereafter.

As shown in Fig. 1, the asymmetric unit is composed of one ethanolaminium cation, half a succinate anion, and half a succinic acid molecule. The succinate anion and succinic acid molecule are linked by an O2—H2···O4 hydrogen bond (Table 1), then are associated with ethanolaminium cation by an O5—H5···O4 hydrogen bond. The distances of [C1—O1 1.2187 (18) Å and C1—O2 1.3009 (18) Å] indicate a carboxylic group, where C1—O1 stands for the carbonyl C=O bond. The distances of [C3—O3 1.2310 (18) Å and C3—O4 1.2831 (17) Å] indicate a carboxylate anion, where the C—O and C=O bonds are equalized, and no distinct carbonyl C=O bond is observed (Borthwick, 1980). This is mixed mode of succinate and succinic acid, and is similar to those observed in other cases (Prasad & Vijayan, 1990; Li et al., 2003; Bruno et al., 2004).

The succinate anion and the succinic acid molecule are arranged almost in the same layers (Fig. 2), and the ethanolaminium cation are sandwiched between the layers by O—H···O and N—H···O hydrogen bonds (Table 1).

Related literature top

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 top

Succinic acid (5.1 g) and ethanolamine (2.4 g), in a molar ratio of 1:1, were mixed and dissolved in sufficient ethanol by heating to 373 K, at which point a clear solution resulted. The system was then cooled slowly to room temperature. Crystals of (I) (4.3 g) were formed, collected and washed with ethanol.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Hydrogen bonds are illustrated as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed down the c axis. Hydrogen bonds are drawn as dashed lines.

Bis(ethanolaminium) succinate–succinic acid (1/1) top

Crystal data top

2C₂H₈NO⁺·C₄H₄O₄²⁻·C₄H₆O₄	Z = 1
M_r = 358.35	F(000) = 192.0
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0582P)² + 0.1261P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1628 reflections	Δρ_max = 0.37 e Å⁻³
110 parameters	Δρ_min = −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)

Crystal data top

2C₂H₈NO⁺·C₄H₄O₄²⁻·C₄H₆O₄	γ = 80.380 (12)°
M_r = 358.35	V = 421.2 (6) Å³
Triclinic, P1	Z = 1
a = 5.821 (5) Å	Mo Kα radiation
b = 8.428 (7) Å	µ = 0.12 mm⁻¹
c = 9.077 (7) Å	T = 293 K
α = 87.74 (1)°	0.42 × 0.34 × 0.30 mm
β = 73.628 (11)°

Data collection top

Bruker APEX area-detector diffractometer	1628 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1517 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.898	R_int = 0.011
2330 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.37 e Å⁻³
1628 reflections	Δρ_min = −0.32 e Å⁻³
110 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.89	1.93	2.810 (2)	167
N1—H1C···O5	0.89	2.55	2.868 (3)	102
N1—H1C···O5^v	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: (iii) x−1, y, z+1; (iv) x−1, y, z; (v) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	2C₂H₈NO⁺·C₄H₄O₄²⁻·C₄H₆O₄
M_r	358.35
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.821 (5), 8.428 (7), 9.077 (7)
α, β, γ (°)	87.74 (1), 73.628 (11), 80.380 (12)
V (Å³)	421.2 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.42 × 0.34 × 0.30

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.855, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	2330, 1628, 1517
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.106, 1.07
No. of reflections	1628
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.32

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z+1; (ii) x−1, y, z; (iii) −x, −y+2, −z+2.

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