organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Bis(2-hy­dr­oxy­ethanaminium) terephthalate

aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
*Correspondence e-mail: jinyunihao@yahoo.cn

(Received 13 December 2011; accepted 4 January 2012; online 11 January 2012)

The asymmetric unit of the title salt, 2C2H8NO+·C8H4O42−, comprises one crystallographically independent 2-hy­droxy­ethanaminium cation and one half terephthalate anion. In the crystal, hydrogen bonds involving the hy­droxy and ammonium groups of the cations and the carboxyl­ate O atoms of the terephthalate anions result in the formation of a three-dimensional network structure.

Related literature

For compounds containing the terephthalate anion, see: Zhang et al. (2005[Zhang, H.-M., Lu, L.-P., Feng, S.-S., Qin, S.-D. & Zhu, M.-L. (2005). Acta Cryst. E61, m1027-m1029.]); Smith & Wermuth (2010[Smith, G. & Wermuth, U. D. (2010). Acta Cryst. C66, o575-o580.]); Karpova et al. (2004[Karpova, E. V., Zakharov, M. A., Gutnikov, S. I. & Alekseyev, R. S. (2004). Acta Cryst. E60, o2491-o2492.]). For their physical properties, see: Ye et al. (2006[Ye, Q., Song, Y.-M., Wang, G.-X., Chen, K. & Fu, D.-W. (2006). J. Am. Chem. Soc. 128, 6554-6555.]); Zhang et al. (2008[Zhang, W., Xiong, R.-G. & Huang, S.-P. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.], 2009[Zhang, W., Li, Z.-C., Xiong, R.-G., Nakamura, T. & Huang, S.-P. (2009). J. Am. Chem. Soc. 131, 12544-12545.], 2010[Zhang, W., Ye, H.-Y., Cai, H.-L., Ge, J.-Z. & Xiong, R.-G. (2010). J. Am. Chem. Soc. 132, 7300-7302.]); Fu et al. (2009[Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994-997.]); Wu et al. (2011[Wu, D.-H., Ge, J.-Z., Cai, H.-L., Zhang, W. & Xiong, R.-G. (2011). CrystEngComm, 13, 319-324.]).

[Scheme 1]

Experimental

Crystal data
  • 2C2H8NO+·C8H4O42−

  • Mr = 288.30

  • Monoclinic, P 21 /n

  • a = 9.3578 (19) Å

  • b = 7.8579 (16) Å

  • c = 9.844 (2) Å

  • β = 110.53 (3)°

  • V = 677.9 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.3 × 0.3 × 0.2 mm

Data collection
  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.489, Tmax = 1.000

  • 6639 measured reflections

  • 1558 independent reflections

  • 1270 reflections with I > 2σ(I)

  • Rint = 0.068

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.108

  • S = 1.05

  • 1558 reflections

  • 92 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O3i 0.82 1.92 2.7373 (15) 179
N1—H1F⋯O3ii 0.89 2.03 2.8995 (16) 164
N1—H1C⋯O3iii 0.89 2.15 2.9725 (16) 154
N1—H1B⋯O2iv 0.89 1.80 2.6792 (15) 169
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x-1, y, z; (iv) -x+1, -y, -z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Several crystal structures containing terephthalate anion have been reported previously (Zhang et al., 2005; Smith & Wermuth, 2010; Karpova et al., 2004) as well as their physical properties (Zhang et al., 2010; Zhang et al., 2008; Wu et al., 2011). We report here the crystal structure of the title compound, Fig.1. The asymmetric unit of the title salt, 2(C2H8NO)+. (C8H4O4)2- comprises one crystallographically independent 2-hydroxyethanaminium cation and one-half-terephthalate anion. In the crystal structure, hydrogen bonds involving the hydroxy and ammonium groups connect the carboxyl O atoms of the terephthalate anion into a three-dimensional network structure, Figure 2, Table1.

Related literature top

For compounds containing the terephthalate anion, see: Zhang et al. (2005); Smith & Wermuth (2010); Karpova et al. (2004). For their physical properties, see: Ye et al. (2006); Zhang et al. (2008, 2009, 2010); Fu et al. (2009); Wu et al. (2011).

Experimental top

The title compound was synthetized from a mixture of NH2(CH2)2OH (122.16 mg, 2.00 mmol), C8H6O4 (166.13 mg, 1.00 mmol), and distilled water (10 mL), which was stirred a few minutes at room temperature, giving a clear transparent solution. After evaporation for a few days, block colorless crystals suitable for X-ray diffraction were obtained in about 77% yield, which were filtered and washed with distilled water.

Refinement top

H atoms bound to carbon and nitrogen were placed at idealized positions [C—H = 0.93 to 0.97 Å, N—H = 0.89 Å and O—H = 0.82 Å] and allowed to ride on their parent atoms with Uiso fixed at 1.2 Ueq(C,N).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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
[Figure 1] Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level.Symmetry code (A): 2-x,-y,1-z
[Figure 2] Fig. 2. A view of the association between ions in bis (2-hydroxyethanaminium) terephthalate, showing the hydrogen bonds interactions. Symmetry code: (i) x-1/2, -y+1/2, z+1/2; (ii) -x+3/2, y-1/2, -z+1/2; (iii) x-1, y, z; (iv) -x+1, -y, -z.
Bis(2-hydroxyethanaminium) terephthalate top
Crystal data top
2C2H8NO+·C8H4O42F(000) = 308
Mr = 288.30Dx = 1.412 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3450 reflections
a = 9.3578 (19) Åθ = 6.2–55.3°
b = 7.8579 (16) ŵ = 0.11 mm1
c = 9.844 (2) ÅT = 293 K
β = 110.53 (3)°Block, colorless
V = 677.9 (2) Å30.3 × 0.3 × 0.2 mm
Z = 2
Data collection top
Rigaku Mercury CCD
diffractometer
1558 independent reflections
Radiation source: fine-focus sealed tube1270 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
h = 1212
Tmin = 0.489, Tmax = 1.000k = 1010
6639 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0417P)2 + 0.0687P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1558 reflectionsΔρmax = 0.29 e Å3
92 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.330 (17)
Crystal data top
2C2H8NO+·C8H4O42V = 677.9 (2) Å3
Mr = 288.30Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.3578 (19) ŵ = 0.11 mm1
b = 7.8579 (16) ÅT = 293 K
c = 9.844 (2) Å0.3 × 0.3 × 0.2 mm
β = 110.53 (3)°
Data collection top
Rigaku Mercury CCD
diffractometer
1558 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1270 reflections with I > 2σ(I)
Tmin = 0.489, Tmax = 1.000Rint = 0.068
6639 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.05Δρmax = 0.29 e Å3
1558 reflectionsΔρmin = 0.21 e Å3
92 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
xyzUiso*/Ueq
C10.52569 (16)0.15091 (18)0.33959 (14)0.0269 (3)
H1D0.55970.05140.40070.032*
H1E0.61410.22020.34760.032*
C20.44639 (17)0.09872 (18)0.18647 (14)0.0280 (4)
H2A0.41380.19920.12620.034*
H2B0.51640.03560.15250.034*
C31.10759 (16)0.09307 (16)0.46571 (14)0.0229 (3)
H3A1.18090.15520.44320.028*
C40.97258 (15)0.04996 (15)0.35739 (12)0.0196 (3)
C50.86558 (16)0.04471 (16)0.39320 (14)0.0226 (3)
H5A0.77470.07580.32090.027*
C60.93996 (16)0.10265 (16)0.20297 (13)0.0216 (3)
N10.31233 (13)0.00831 (14)0.17323 (11)0.0251 (3)
H1B0.26610.03800.08090.038*
H1C0.24770.05000.20360.038*
H1F0.34250.10140.22720.038*
O10.42127 (12)0.24468 (13)0.38314 (11)0.0356 (3)
H1A0.45840.26420.47040.053*
O20.81514 (12)0.05985 (13)0.11320 (10)0.0318 (3)
O31.04092 (11)0.18757 (12)0.17413 (10)0.0281 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0241 (8)0.0296 (7)0.0252 (8)0.0011 (6)0.0065 (6)0.0043 (5)
C20.0305 (8)0.0314 (7)0.0234 (8)0.0052 (6)0.0111 (6)0.0034 (5)
C30.0221 (7)0.0273 (7)0.0189 (7)0.0028 (5)0.0065 (6)0.0027 (5)
C40.0222 (7)0.0210 (6)0.0144 (7)0.0021 (5)0.0047 (6)0.0004 (5)
C50.0192 (7)0.0281 (7)0.0166 (7)0.0013 (5)0.0016 (6)0.0002 (5)
C60.0267 (8)0.0214 (6)0.0153 (7)0.0039 (5)0.0057 (6)0.0009 (5)
N10.0293 (7)0.0247 (6)0.0182 (6)0.0022 (5)0.0045 (5)0.0027 (4)
O10.0294 (6)0.0461 (7)0.0268 (6)0.0065 (5)0.0041 (5)0.0143 (4)
O20.0281 (6)0.0443 (6)0.0166 (6)0.0036 (4)0.0000 (5)0.0042 (4)
O30.0340 (6)0.0312 (6)0.0187 (5)0.0054 (4)0.0086 (4)0.0040 (4)
Geometric parameters (Å, º) top
C1—O11.4055 (15)C4—C51.3885 (18)
C1—C21.485 (2)C4—C61.5000 (17)
C1—H1D0.9700C5—C3i1.3755 (18)
C1—H1E0.9700C5—H5A0.9300
C2—N11.4776 (17)C6—O21.2387 (18)
C2—H2A0.9700C6—O31.2676 (15)
C2—H2B0.9700N1—H1B0.8900
C3—C5i1.3755 (18)N1—H1C0.8900
C3—C41.3795 (19)N1—H1F0.8900
C3—H3A0.9300O1—H1A0.8200
O1—C1—C2107.52 (11)C3—C4—C6121.42 (12)
O1—C1—H1D110.2C5—C4—C6119.78 (12)
C2—C1—H1D110.2C3i—C5—C4120.79 (13)
O1—C1—H1E110.2C3i—C5—H5A119.6
C2—C1—H1E110.2C4—C5—H5A119.6
H1D—C1—H1E108.5O2—C6—O3125.00 (12)
N1—C2—C1110.69 (10)O2—C6—C4117.00 (12)
N1—C2—H2A109.5O3—C6—C4118.01 (12)
C1—C2—H2A109.5C2—N1—H1B109.5
N1—C2—H2B109.5C2—N1—H1C109.5
C1—C2—H2B109.5H1B—N1—H1C109.5
H2A—C2—H2B108.1C2—N1—H1F109.5
C5i—C3—C4120.40 (12)H1B—N1—H1F109.5
C5i—C3—H3A119.8H1C—N1—H1F109.5
C4—C3—H3A119.8C1—O1—H1A109.5
C3—C4—C5118.81 (11)
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O3ii0.821.922.7373 (15)179
N1—H1F···O3iii0.892.032.8995 (16)164
N1—H1C···O3iv0.892.152.9725 (16)154
N1—H1B···O2v0.891.802.6792 (15)169
Symmetry codes: (ii) x1/2, y+1/2, z+1/2; (iii) x+3/2, y1/2, z+1/2; (iv) x1, y, z; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula2C2H8NO+·C8H4O42
Mr288.30
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)9.3578 (19), 7.8579 (16), 9.844 (2)
β (°) 110.53 (3)
V3)677.9 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.3 × 0.3 × 0.2
Data collection
DiffractometerRigaku Mercury CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.489, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6639, 1558, 1270
Rint0.068
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.108, 1.05
No. of reflections1558
No. of parameters92
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.21

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O3i0.821.922.7373 (15)178.7
N1—H1F···O3ii0.892.032.8995 (16)163.6
N1—H1C···O3iii0.892.152.9725 (16)154.3
N1—H1B···O2iv0.891.802.6792 (15)169.2
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+3/2, y1/2, z+1/2; (iii) x1, y, z; (iv) x+1, y, z.
 

Acknowledgements

The author thanks the Ordered Matter Science Research Center, Southeast University for its excellent experimental conditions and its generous financial support.

References

First citationFu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994–997.  Web of Science CSD CrossRef CAS Google Scholar
First citationKarpova, E. V., Zakharov, M. A., Gutnikov, S. I. & Alekseyev, R. S. (2004). Acta Cryst. E60, o2491–o2492.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSmith, G. & Wermuth, U. D. (2010). Acta Cryst. C66, o575–o580.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWu, D.-H., Ge, J.-Z., Cai, H.-L., Zhang, W. & Xiong, R.-G. (2011). CrystEngComm, 13, 319–324.  Web of Science CSD CrossRef CAS Google Scholar
First citationYe, Q., Song, Y.-M., Wang, G.-X., Chen, K. & Fu, D.-W. (2006). J. Am. Chem. Soc. 128, 6554–6555.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationZhang, W., Li, Z.-C., Xiong, R.-G., Nakamura, T. & Huang, S.-P. (2009). J. Am. Chem. Soc. 131, 12544–12545.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationZhang, H.-M., Lu, L.-P., Feng, S.-S., Qin, S.-D. & Zhu, M.-L. (2005). Acta Cryst. E61, m1027–m1029.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZhang, W., Xiong, R.-G. & Huang, S.-P. D. (2008). J. Am. Chem. Soc. 130, 10468–10469.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationZhang, W., Ye, H.-Y., Cai, H.-L., Ge, J.-Z. & Xiong, R.-G. (2010). J. Am. Chem. Soc. 132, 7300–7302.  Web of Science CSD CrossRef CAS PubMed Google Scholar

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