1,4-Bis(imidazol-1-yl)benzene-terephthalic acid (1/1).

In the title compound, C(12)H(10)N(4)·C(8)H(6)O(4), 1,4-bis-(imidazol-1-yl)benzene and terephthalic acid mol-ecules are joined via strong O-H⋯N hydrogen bonds to form infinite zigzag chains. Both mol-ecules are located on crystallographic inversion centers. The O-H⋯N hydrogen-bonded chains are assembled into two-dimensional layers through weak C-H⋯O and strong π-π stacking inter-actions [centroid-centroid distance = 3.818 (2) Å], leading to the formation of a three-dimensional supra-molecular structure.

Related literature

For general background, see: Aakeröy et al. (2006 ▶); Aakeröy & Seddon (1993 ▶); Desiraju, 2007 ▶; Corna et al. (2004 ▶); Dobrzanska et al. (2006); Van Roey et al. (1991 ▶). For similar structures, see: Wang et al. (2007 ▶); Su et al. (2007 ▶).

Experimental

Crystal data

C12H10N4·C8H6O4

M = 376.37

Monoclinic,

a = 5.2780 (17) Å

b = 10.599 (5) Å

c = 15.449 (5) Å

β = 91.17 (3)°

V = 864.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.25 × 0.22 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

1895 measured reflections

1538 independent reflections

904 reflections with I > 2σ(I)

R int = 0.008

3 standard reflections every 200 reflections intensity decay: 2.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 0.95

1538 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040324/zl2155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040324/zl2155Isup2.hkl

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

C12H10N4·C8H6O4	F(000) = 392
Mr = 376.37	Dx = 1.447 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 18 reflections
a = 5.2780 (17) Å	θ = 4.5–7.6°
b = 10.599 (5) Å	µ = 0.10 mm−1
c = 15.449 (5) Å	T = 293 K
β = 91.17 (3)°	Block, colourless
V = 864.1 (6) Å3	0.25 × 0.22 × 0.15 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0.008
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.3°
graphite	h = −6→6
ω/2θ scans	k = 0→12
1895 measured reflections	l = −9→18
1538 independent reflections	3 standard reflections every 200 reflections
904 reflections with I > 2σ(I)	intensity decay: 2.5%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0842P)2] where P = (Fo2 + 2Fc2)/3
1538 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. 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 > 2sigma(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.

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
N1	0.3750 (4)	0.57026 (17)	0.12218 (11)	0.0403 (5)
N2	0.7031 (4)	0.5588 (2)	0.21140 (12)	0.0489 (6)
C1	0.0819 (5)	0.6228 (2)	0.00451 (16)	0.0467 (6)
H1A	0.1382	0.7059	0.0073	0.056*
C2	−0.1041 (5)	0.5891 (2)	−0.05539 (15)	0.0467 (6)
H2	−0.1745	0.6495	−0.0923	0.056*
C3	0.1844 (4)	0.5339 (2)	0.06017 (13)	0.0375 (5)
C4	0.5583 (4)	0.4962 (2)	0.15707 (14)	0.0445 (6)
H4	0.5788	0.4112	0.1440	0.053*
C5	0.6087 (5)	0.6786 (2)	0.21254 (16)	0.0531 (7)
H5	0.6740	0.7444	0.2460	0.064*
C6	0.4073 (3)	0.68757 (13)	0.15820 (8)	0.0504 (7)
H6	0.3095	0.7590	0.1472	0.061*
O1	0.0950 (3)	0.49725 (13)	0.30802 (8)	0.0499 (5)
H1	−0.0288	0.5179	0.2784	0.075*
O2	0.0072 (4)	0.67524 (16)	0.37876 (12)	0.0601 (6)
C7	0.1260 (5)	0.5775 (2)	0.37186 (15)	0.0428 (6)
C8	0.3231 (4)	0.5370 (2)	0.43721 (14)	0.0387 (6)
C9	0.5136 (4)	0.4536 (2)	0.41709 (14)	0.0415 (6)
H9	0.5236	0.4221	0.3611	0.050*
C10	0.6897 (4)	0.4164 (2)	0.47922 (14)	0.0435 (6)
H10	0.8171	0.3600	0.4650	0.052*

	U11	U22	U33	U12	U13	U23
N1	0.0420 (11)	0.0393 (11)	0.0391 (10)	0.0033 (9)	−0.0132 (9)	0.0005 (8)
N2	0.0476 (12)	0.0568 (13)	0.0415 (11)	−0.0001 (11)	−0.0184 (9)	−0.0007 (9)
C1	0.0516 (15)	0.0374 (12)	0.0504 (13)	0.0036 (11)	−0.0187 (12)	0.0008 (10)
C2	0.0542 (15)	0.0390 (13)	0.0460 (12)	0.0053 (12)	−0.0196 (11)	0.0056 (10)
C3	0.0369 (12)	0.0418 (13)	0.0334 (11)	0.0059 (10)	−0.0102 (9)	−0.0028 (9)
C4	0.0446 (13)	0.0476 (14)	0.0405 (12)	0.0064 (12)	−0.0176 (10)	−0.0021 (10)
C5	0.0619 (16)	0.0460 (14)	0.0506 (14)	−0.0053 (13)	−0.0198 (12)	−0.0023 (12)
C6	0.0588 (16)	0.0377 (14)	0.0539 (15)	0.0035 (12)	−0.0198 (13)	−0.0039 (11)
O1	0.0495 (10)	0.0531 (10)	0.0462 (9)	0.0021 (8)	−0.0205 (7)	−0.0019 (8)
O2	0.0645 (12)	0.0425 (10)	0.0720 (13)	0.0053 (9)	−0.0335 (10)	−0.0041 (9)
C7	0.0400 (13)	0.0422 (14)	0.0457 (13)	−0.0084 (12)	−0.0128 (11)	0.0030 (11)
C8	0.0412 (13)	0.0335 (12)	0.0409 (12)	−0.0106 (10)	−0.0133 (10)	0.0058 (9)
C9	0.0427 (13)	0.0441 (13)	0.0372 (11)	−0.0040 (11)	−0.0087 (10)	−0.0003 (10)
C10	0.0363 (13)	0.0440 (14)	0.0498 (13)	−0.0044 (11)	−0.0083 (11)	0.0019 (11)

N1—C4	1.349 (3)	C5—H5	0.9300
N1—C6	1.371 (2)	C6—H6	0.9300
N1—C3	1.428 (3)	O1—C7	1.31010
N2—C4	1.305 (3)	O1—H1	0.8200
N2—C5	1.364 (3)	O2—C7	1.217 (3)
C1—C3	1.379 (3)	C7—C8	1.498 (3)
C1—C2	1.383 (3)	C8—C9	1.379 (3)
C1—H1A	0.9300	C8—C10ii	1.385 (3)
C2—C3i	1.372 (3)	C9—C10	1.380 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C2i	1.372 (3)	C10—C8ii	1.385 (3)
C4—H4	0.9300	C10—H10	0.9300
C5—C6	1.344 (3)
C4—N1—C6	106.45 (17)	N2—C5—H5	125.0
C4—N1—C3	126.9 (2)	C5—C6—N1	106.22 (16)
C6—N1—C3	126.66 (17)	C5—C6—H6	126.9
C4—N2—C5	105.8 (2)	N1—C6—H6	126.9
C3—C1—C2	120.3 (2)	C7—O1—H1	109.5
C3—C1—H1A	119.8	O2—C7—O1	124.20
C2—C1—H1A	119.8	O2—C7—C8	122.5 (2)
C3i—C2—C1	119.7 (2)	O1—C7—C8	113.31
C3i—C2—H2	120.1	C9—C8—C10ii	119.2 (2)
C1—C2—H2	120.1	C9—C8—C7	122.1 (2)
C2i—C3—C1	119.9 (2)	C10ii—C8—C7	118.7 (2)
C2i—C3—N1	120.35 (19)	C8—C9—C10	120.7 (2)
C1—C3—N1	119.7 (2)	C8—C9—H9	119.7
N2—C4—N1	111.5 (2)	C10—C9—H9	119.7
N2—C4—H4	124.2	C9—C10—C8ii	120.1 (2)
N1—C4—H4	124.2	C9—C10—H10	119.9
C6—C5—N2	110.01 (19)	C8ii—C10—H10	119.9
C6—C5—H5	125.0
C3—C1—C2—C3i	−0.9 (4)	N2—C5—C6—N1	0.0 (3)
C2—C1—C3—C2i	0.9 (4)	C4—N1—C6—C5	0.3 (2)
C2—C1—C3—N1	−179.5 (2)	C3—N1—C6—C5	−179.9 (2)
C4—N1—C3—C2i	26.8 (4)	O2—C7—C8—C9	−157.3 (2)
C6—N1—C3—C2i	−153.0 (2)	O1—C7—C8—C9	23.07
C4—N1—C3—C1	−152.9 (2)	O2—C7—C8—C10ii	23.6 (4)
C6—N1—C3—C1	27.3 (3)	O1—C7—C8—C10ii	−155.90
C5—N2—C4—N1	0.5 (3)	C10ii—C8—C9—C10	0.2 (4)
C6—N1—C4—N2	−0.5 (3)	C7—C8—C9—C10	−178.8 (2)
C3—N1—C4—N2	179.6 (2)	C8—C9—C10—C8ii	−0.2 (4)
C4—N2—C5—C6	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2iii	0.82	1.79	2.60885	178
C2—H2···O2iv	0.93	2.54	3.376 (3)	150
C4—H4···O2v	0.93	2.56	3.463 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.82	1.79	2.60885	178
C2—H2⋯O2ii	0.93	2.54	3.376 (3)	150
C4—H4⋯O2iii	0.93	2.56	3.463 (3)	162

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