Tetra-methyl-ammonium hydrogen terephthalate.

The asymmetric unit of the title salt, C(4)H(12)N(+)·C(8)H(5)O(4) (-), contains one half of a tetra-methyl-ammonium cation and one half of a hydrogen terephthalate monoanion. The N atom of the ammonium cation lies on a twofold rotation axis and the centre of mass of the terephthalate anion is on a centre of inversion. In the crystal, the centrosymmetric terephthalate ions are linked by a very short symmetric O-H⋯O hydrogen bond [O⋯O = 2.4610 (19) Å] into a one-dimensional polymeric chain along [1-12]. The tetra-methyl-ammonium cations and terephthalate anions are then connected through a pair of bifurcated acceptor C-H⋯O hydrogen bonds, generating a three-dimensional supra-molecular network. The carboxyl-ate groups at both ends of the terephthalate anion are charge-shared with an equal probability of 0.5.

Related literature

For a review of very short O—H⋯O hydrogen bonds, see: Speakman (1972 ▶). For recent reports of acidic salts of dicarb­oxy­lic acids with short intra- and inter­molecular O—H⋯O hydrogen bonds, see: Starosta & Leciejewicz (2010 ▶); Hemamalini & Fun (2010 ▶); Sun et al. (2002 ▶); Sharma et al. (2006 ▶); Wang et al. (2004 ▶); Taka et al. (1998 ▶). For examples of diphospho­nates with strong O—H⋯O hydrogen bonds, see: Tsaryk et al. (2011 ▶); Courtney et al. (2006 ▶); Cheng & Lin (2006 ▶). For background to symmetric and asymmetric O—H⋯O hydrogen bonds, see: Misaki et al. (1986 ▶); Catti & Ferraris (1976 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For the synthesis of the 5,5′-(o-phenyl­ene)di-1H-tetra­zole ligand, see: Demko & Sharpless (2001 ▶).

Experimental

Crystal data

C4H12N+·C8H5O4 −

M = 239.27

Monoclinic,

a = 16.0585 (4) Å

b = 9.1527 (2) Å

c = 11.5866 (3) Å

β = 132.915 (2)°

V = 1247.21 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.42 × 0.37 × 0.32 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.708, T max = 0.746

20680 measured reflections

1360 independent reflections

1269 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.147

S = 1.07

1360 reflections

80 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (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: XPW (Siemens, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039487/bg2478sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039487/bg2478Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039487/bg2478Isup3.cml

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

C4H12N+·C8H5O4−	F(000) = 512
Mr = 239.27	Dx = 1.274 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9931 reflections
a = 16.0585 (4) Å	θ = 2.8–30.3°
b = 9.1527 (2) Å	µ = 0.10 mm−1
c = 11.5866 (3) Å	T = 298 K
β = 132.915 (2)°	Irregular, colourless
V = 1247.21 (7) Å3	0.42 × 0.37 × 0.32 mm
Z = 4

Bruker APEXII CCD diffractometer	1360 independent reflections
Radiation source: fine-focus sealed tube	1269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→20
Tmin = 0.708, Tmax = 0.746	k = −11→11
20680 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0714P)2 + 1.1167P] where P = (Fo2 + 2Fc2)/3
1360 reflections	(Δ/σ)max < 0.001
80 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O2	0.32784 (9)	0.78319 (13)	0.13940 (12)	0.0451 (4)
C5	0.51647 (12)	0.89007 (16)	0.43479 (16)	0.0341 (4)
H5	0.5278	0.8165	0.3914	0.041*
C4	0.40806 (11)	0.94633 (15)	0.34990 (15)	0.0312 (3)
C6	0.30731 (12)	0.89045 (17)	0.18691 (16)	0.0363 (4)
O1	0.21412 (12)	0.94615 (19)	0.11216 (16)	0.0789 (6)
N	0.5000	0.3608 (2)	0.2500	0.0416 (5)
C9	0.4511 (2)	0.4550 (3)	0.2947 (3)	0.0794 (8)
H9A	0.5097	0.5155	0.3823	0.119*
H9B	0.4188	0.3951	0.3239	0.119*
H9C	0.3928	0.5157	0.2070	0.119*
C3	0.39205 (12)	1.05665 (16)	0.41571 (16)	0.0353 (4)
H3	0.3198	1.0950	0.3594	0.042*
C8	0.58943 (19)	0.2666 (3)	0.3849 (3)	0.0695 (6)
H8A	0.6473	0.3266	0.4737	0.104*
H8B	0.6224	0.2071	0.3565	0.104*
H8C	0.5565	0.2049	0.4120	0.104*
H2	0.2500	0.7500	0.0000	0.098 (13)*

	U11	U22	U33	U12	U13	U23
O2	0.0364 (6)	0.0526 (7)	0.0300 (6)	−0.0050 (5)	0.0162 (5)	−0.0175 (5)
C5	0.0348 (7)	0.0345 (7)	0.0276 (7)	−0.0003 (5)	0.0191 (6)	−0.0076 (5)
C4	0.0315 (7)	0.0324 (7)	0.0218 (6)	−0.0030 (5)	0.0150 (6)	−0.0043 (5)
C6	0.0319 (7)	0.0405 (8)	0.0235 (6)	−0.0026 (6)	0.0138 (6)	−0.0054 (5)
O1	0.0420 (7)	0.0938 (12)	0.0411 (7)	0.0188 (7)	0.0048 (6)	−0.0263 (7)
N	0.0410 (10)	0.0367 (9)	0.0405 (10)	0.000	0.0252 (9)	0.000
C9	0.0718 (15)	0.0875 (17)	0.0706 (14)	0.0197 (12)	0.0452 (13)	−0.0130 (12)
C3	0.0292 (7)	0.0373 (8)	0.0278 (7)	0.0024 (5)	0.0149 (6)	−0.0043 (5)
C8	0.0627 (13)	0.0587 (12)	0.0605 (13)	0.0133 (10)	0.0315 (11)	0.0174 (10)

O2—C6	1.2739 (19)	N—C8	1.481 (2)
C5—C4	1.390 (2)	C9—H9A	0.9600
C5—C3i	1.3896 (19)	C9—H9B	0.9600
C5—H5	0.9300	C9—H9C	0.9600
C4—C3	1.391 (2)	C3—C5i	1.3896 (19)
C4—C6	1.5115 (18)	C3—H3	0.9300
C6—O1	1.218 (2)	C8—H8A	0.9600
N—C9ii	1.478 (2)	C8—H8B	0.9600
N—C9	1.478 (2)	C8—H8C	0.9600
N—C8ii	1.481 (2)
C4—C5—C3i	120.25 (13)	N—C9—H9A	109.5
C4—C5—H5	119.9	N—C9—H9B	109.5
C3i—C5—H5	119.9	H9A—C9—H9B	109.5
C5—C4—C3	119.41 (12)	N—C9—H9C	109.5
C5—C4—C6	121.22 (12)	H9A—C9—H9C	109.5
C3—C4—C6	119.37 (13)	H9B—C9—H9C	109.5
O1—C6—O2	124.70 (13)	C5i—C3—C4	120.33 (13)
O1—C6—C4	119.89 (14)	C5i—C3—H3	119.8
O2—C6—C4	115.39 (13)	C4—C3—H3	119.8
C9ii—N—C9	108.6 (3)	N—C8—H8A	109.5
C9ii—N—C8ii	109.57 (15)	N—C8—H8B	109.5
C9—N—C8ii	110.17 (15)	H8A—C8—H8B	109.5
C9ii—N—C8	110.17 (15)	N—C8—H8C	109.5
C9—N—C8	109.57 (15)	H8A—C8—H8C	109.5
C8ii—N—C8	108.7 (2)	H8B—C8—H8C	109.5
C3i—C5—C4—C3	0.2 (3)	C5—C4—C6—O2	4.7 (2)
C3i—C5—C4—C6	179.82 (13)	C3—C4—C6—O2	−175.69 (14)
C5—C4—C6—O1	−176.70 (17)	C5—C4—C3—C5i	−0.2 (3)
C3—C4—C6—O1	2.9 (2)	C6—C4—C3—C5i	−179.83 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O2iii	1.23	1.23	2.4610 (19)	180 (1)
C8—H8A···O1iv	0.96	2.39	3.267 (3)	152
C9—H9A···O1iv	0.96	2.47	3.321 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O2i	1.23	1.23	2.4610 (19)	180 (1)
C8—H8A⋯O1ii	0.96	2.39	3.267 (3)	152
C9—H9A⋯O1ii	0.96	2.47	3.321 (3)	148

Symmetry codes: (i) ; (ii) .