Bis(2-hy­droxy­ethanaminium) terephthalate

Jin, Y.

doi:10.1107/S1600536812000293

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o336

doi:10.1107/S1600536812000293

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Bis(2-hydroxyethanaminium) terephthalate

Yu Jin ^a ^*

^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 ); 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

Crystal data

2C₂H₈NO⁺·C₈H₄O₄²⁻
M_r = 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 ) T_min = 0.489, T_max = 1.000
6639 measured reflections
1558 independent reflections
1270 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.108
S = 1.05
1558 reflections
92 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O2^iv	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); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536812000293/bx2389sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000293/bx2389Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000293/bx2389Isup3.cml

checkCIF report

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.

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

	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
	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⁺·C₈H₄O₄²⁻	F(000) = 308
M_r = 288.30	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3450 reflections
a = 9.3578 (19) Å	θ = 6.2–55.3°
b = 7.8579 (16) Å	µ = 0.11 mm⁻¹
c = 9.844 (2) Å	T = 293 K
β = 110.53 (3)°	Block, colorless
V = 677.9 (2) Å³	0.3 × 0.3 × 0.2 mm
Z = 2

Data collection top

Rigaku Mercury CCD diffractometer	1558 independent reflections
Radiation source: fine-focus sealed tube	1270 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ω scans	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −12→12
T_min = 0.489, T_max = 1.000	k = −10→10
6639 measured reflections	l = −12→12

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0417P)² + 0.0687P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1558 reflections	Δρ_max = 0.29 e Å⁻³
92 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.330 (17)

Crystal data top

2C₂H₈NO⁺·C₈H₄O₄²⁻	V = 677.9 (2) Å³
M_r = 288.30	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3578 (19) Å	µ = 0.11 mm⁻¹
b = 7.8579 (16) Å	T = 293 K
c = 9.844 (2) Å	0.3 × 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)
T_min = 0.489, T_max = 1.000	R_int = 0.068
6639 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
1558 reflections	Δρ_min = −0.21 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.52569 (16)	0.15091 (18)	0.33959 (14)	0.0269 (3)
H1D	0.5597	0.0514	0.4007	0.032*
H1E	0.6141	0.2202	0.3476	0.032*
C2	0.44639 (17)	0.09872 (18)	0.18647 (14)	0.0280 (4)
H2A	0.4138	0.1992	0.1262	0.034*
H2B	0.5164	0.0356	0.1525	0.034*
C3	1.10759 (16)	0.09307 (16)	0.46571 (14)	0.0229 (3)
H3A	1.1809	0.1552	0.4432	0.028*
C4	0.97258 (15)	0.04996 (15)	0.35739 (12)	0.0196 (3)
C5	0.86558 (16)	−0.04471 (16)	0.39320 (14)	0.0226 (3)
H5A	0.7747	−0.0758	0.3209	0.027*
C6	0.93996 (16)	0.10265 (16)	0.20297 (13)	0.0216 (3)
N1	0.31233 (13)	−0.00831 (14)	0.17323 (11)	0.0251 (3)
H1B	0.2661	−0.0380	0.0809	0.038*
H1C	0.2477	0.0500	0.2036	0.038*
H1F	0.3425	−0.1014	0.2272	0.038*
O1	0.42127 (12)	0.24468 (13)	0.38314 (11)	0.0356 (3)
H1A	0.4584	0.2642	0.4704	0.053*
O2	0.81514 (12)	0.05985 (13)	0.11320 (10)	0.0318 (3)
O3	1.04092 (11)	0.18757 (12)	0.17413 (10)	0.0281 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0241 (8)	0.0296 (7)	0.0252 (8)	−0.0011 (6)	0.0065 (6)	−0.0043 (5)
C2	0.0305 (8)	0.0314 (7)	0.0234 (8)	−0.0052 (6)	0.0111 (6)	−0.0034 (5)
C3	0.0221 (7)	0.0273 (7)	0.0189 (7)	−0.0028 (5)	0.0065 (6)	0.0027 (5)
C4	0.0222 (7)	0.0210 (6)	0.0144 (7)	0.0021 (5)	0.0047 (6)	0.0004 (5)
C5	0.0192 (7)	0.0281 (7)	0.0166 (7)	−0.0013 (5)	0.0016 (6)	0.0002 (5)
C6	0.0267 (8)	0.0214 (6)	0.0153 (7)	0.0039 (5)	0.0057 (6)	0.0009 (5)
N1	0.0293 (7)	0.0247 (6)	0.0182 (6)	−0.0022 (5)	0.0045 (5)	−0.0027 (4)
O1	0.0294 (6)	0.0461 (7)	0.0268 (6)	0.0065 (5)	0.0041 (5)	−0.0143 (4)
O2	0.0281 (6)	0.0443 (6)	0.0166 (6)	−0.0036 (4)	0.0000 (5)	0.0042 (4)
O3	0.0340 (6)	0.0312 (6)	0.0187 (5)	−0.0054 (4)	0.0086 (4)	0.0040 (4)

Geometric parameters (Å, º) top

C1—O1	1.4055 (15)	C4—C5	1.3885 (18)
C1—C2	1.485 (2)	C4—C6	1.5000 (17)
C1—H1D	0.9700	C5—C3ⁱ	1.3755 (18)
C1—H1E	0.9700	C5—H5A	0.9300
C2—N1	1.4776 (17)	C6—O2	1.2387 (18)
C2—H2A	0.9700	C6—O3	1.2676 (15)
C2—H2B	0.9700	N1—H1B	0.8900
C3—C5ⁱ	1.3755 (18)	N1—H1C	0.8900
C3—C4	1.3795 (19)	N1—H1F	0.8900
C3—H3A	0.9300	O1—H1A	0.8200

O1—C1—C2	107.52 (11)	C3—C4—C6	121.42 (12)
O1—C1—H1D	110.2	C5—C4—C6	119.78 (12)
C2—C1—H1D	110.2	C3ⁱ—C5—C4	120.79 (13)
O1—C1—H1E	110.2	C3ⁱ—C5—H5A	119.6
C2—C1—H1E	110.2	C4—C5—H5A	119.6
H1D—C1—H1E	108.5	O2—C6—O3	125.00 (12)
N1—C2—C1	110.69 (10)	O2—C6—C4	117.00 (12)
N1—C2—H2A	109.5	O3—C6—C4	118.01 (12)
C1—C2—H2A	109.5	C2—N1—H1B	109.5
N1—C2—H2B	109.5	C2—N1—H1C	109.5
C1—C2—H2B	109.5	H1B—N1—H1C	109.5
H2A—C2—H2B	108.1	C2—N1—H1F	109.5
C5ⁱ—C3—C4	120.40 (12)	H1B—N1—H1F	109.5
C5ⁱ—C3—H3A	119.8	H1C—N1—H1F	109.5
C4—C3—H3A	119.8	C1—O1—H1A	109.5
C3—C4—C5	118.81 (11)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱⁱ	0.82	1.92	2.7373 (15)	179
N1—H1F···O3ⁱⁱⁱ	0.89	2.03	2.8995 (16)	164
N1—H1C···O3^iv	0.89	2.15	2.9725 (16)	154
N1—H1B···O2^v	0.89	1.80	2.6792 (15)	169

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

Experimental details

Crystal data
Chemical formula	2C₂H₈NO⁺·C₈H₄O₄²⁻
M_r	288.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.3578 (19), 7.8579 (16), 9.844 (2)
β (°)	110.53 (3)
V (Å³)	677.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.3 × 0.3 × 0.2

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.489, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6639, 1558, 1270
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.108, 1.05
No. of reflections	1558
No. of parameters	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.82	1.92	2.7373 (15)	178.7
N1—H1F···O3ⁱⁱ	0.89	2.03	2.8995 (16)	163.6
N1—H1C···O3ⁱⁱⁱ	0.89	2.15	2.9725 (16)	154.3
N1—H1B···O2^iv	0.89	1.80	2.6792 (15)	169.2

Symmetry codes: (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.

Acknowledgements

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

References

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