Bis(2-hy-droxy-ethanaminium) terephthalate.

The asymmetric unit of the title salt, 2C(2)H(8)NO(+)·C(8)H(4)O(4) (2-), comprises one crystallographically independent 2-hy-droxy-ethanaminium cation and one half terephthalate anion. In the crystal, hydrogen bonds involving the hy-droxy and ammonium groups of the cations and the carboxyl-ate 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+·C8H4O4 2−

M = 288.30

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 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

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000293/bx2389sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812000293/bx2389Isup3.cml

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

2C2H8NO+·C8H4O42−	F(000) = 308
Mr = 288.30	Dx = 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

Rigaku Mercury CCD diffractometer	1558 independent reflections
Radiation source: fine-focus sealed tube	1270 reflections with I > 2σ(I)
graphite	Rint = 0.068
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −12→12
Tmin = 0.489, Tmax = 1.000	k = −10→10
6639 measured reflections	l = −12→12

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(Fo2) + (0.0417P)2 + 0.0687P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1558 reflections	Δρmax = 0.29 e Å−3
92 parameters	Δρmin = −0.20 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)

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
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)

	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)

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)

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···O3iv	0.89	2.15	2.9725 (16)	154
N1—H1B···O2v	0.89	1.80	2.6792 (15)	169

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⋯O2iv	0.89	1.80	2.6792 (15)	169

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