4-Hydroxy-benzoic acid-1H-imidazole (1/1).

In the title 1:1 adduct, C(7)H(6)O(3)·C(3)H(4)N(2), the crystal packing features π-π stacking inter-actions [centroid-centroid distances = 3.799 (2) and 3.753 (1) Å] as well as N-H⋯(O,O) O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Li et al. (2005 ▶); Wan et al. (2005 ▶). For the synthesis, see: Wang et al. (2006 ▶). For bond-length data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C7H6O3·C3H4N2

M = 206.20

Monoclinic,

a = 9.601 (2) Å

b = 10.530 (2) Å

c = 10.586 (2) Å

β = 113.759 (3)°

V = 979.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.47 × 0.29 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.987

5200 measured reflections

1858 independent reflections

1583 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.213

S = 1.11

1858 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016043/at2768sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016043/at2768Isup2.hkl

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

C7H6O3·C3H4N2	F(000) = 440
Mr = 206.20	Dx = 1.398 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2125 reflections
a = 9.601 (2) Å	θ = 2.9–25.6°
b = 10.530 (2) Å	µ = 0.11 mm−1
c = 10.586 (2) Å	T = 293 K
β = 113.759 (3)°	Block, colourless
V = 979.6 (4) Å3	0.47 × 0.29 × 0.10 mm
Z = 4

Siemens SMART 1000 CCD area-detector diffractometer	1858 independent reflections
Radiation source: fine-focus sealed tube	1583 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 8.33 pixels mm-1	θmax = 25.7°, θmin = 2.4°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.955, Tmax = 0.987	l = −12→5
5200 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1212P)2 + 0.6043P] where P = (Fo2 + 2Fc2)/3
1858 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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
O1	−0.0067 (2)	0.60204 (17)	0.30887 (18)	0.0406 (5)
O2	0.1226 (2)	0.62774 (19)	0.53341 (19)	0.0494 (6)
H2	0.1995	0.5993	0.5951	0.080*
C1	0.2147 (3)	0.4753 (2)	0.4208 (2)	0.0376 (6)
N1	−0.0869 (3)	0.8121 (2)	0.4675 (2)	0.0444 (6)
H1	−0.0212	0.7516	0.4899	0.080*
C10	0.1036 (3)	0.5752 (2)	0.4219 (3)	0.0361 (6)
O3	0.5211 (3)	0.1947 (2)	0.4273 (2)	0.0614 (7)
H3	0.5014	0.1663	0.3499	0.080*
C2	0.2031 (3)	0.4185 (3)	0.2978 (3)	0.0421 (7)
H2A	0.1256	0.4433	0.2149	0.080*
C8	−0.2648 (3)	0.9398 (2)	0.3478 (3)	0.0364 (6)
H8	−0.3401	0.9793	0.2727	0.080*
C7	−0.1811 (3)	0.8415 (3)	0.3413 (3)	0.0461 (7)
H7	−0.1880	0.8005	0.2611	0.080*
C4	0.4199 (3)	0.2872 (3)	0.4201 (3)	0.0438 (7)
C6	0.3317 (3)	0.4363 (3)	0.5424 (3)	0.0478 (7)
H6	0.3420	0.4738	0.6253	0.080*
C3	0.3048 (3)	0.3260 (3)	0.2973 (3)	0.0449 (7)
H3A	0.2960	0.2896	0.2143	0.080*
C5	0.4330 (4)	0.3435 (3)	0.5433 (3)	0.0545 (8)
H5	0.5102	0.3183	0.6262	0.080*
N2	−0.2226 (4)	0.9731 (3)	0.4821 (3)	0.0715 (9)
C9	−0.1105 (4)	0.8937 (3)	0.5572 (3)	0.0519 (8)
H9	−0.0586	0.8941	0.6528	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0403 (10)	0.0418 (10)	0.0347 (10)	0.0012 (7)	0.0099 (8)	0.0032 (7)
O2	0.0488 (11)	0.0549 (12)	0.0346 (10)	0.0151 (9)	0.0065 (8)	−0.0054 (8)
C1	0.0384 (13)	0.0386 (13)	0.0336 (13)	−0.0009 (10)	0.0121 (11)	−0.0003 (10)
N1	0.0458 (12)	0.0424 (12)	0.0412 (13)	0.0075 (10)	0.0137 (10)	0.0059 (10)
C10	0.0366 (13)	0.0371 (13)	0.0319 (13)	−0.0023 (10)	0.0108 (10)	0.0022 (9)
O3	0.0610 (13)	0.0710 (15)	0.0436 (12)	0.0277 (11)	0.0122 (10)	−0.0073 (10)
C2	0.0438 (14)	0.0463 (14)	0.0319 (13)	0.0046 (11)	0.0109 (11)	0.0005 (10)
C8	0.0331 (12)	0.0372 (12)	0.0323 (12)	0.0079 (10)	0.0065 (10)	0.0097 (10)
C7	0.0475 (15)	0.0476 (15)	0.0386 (14)	0.0003 (12)	0.0125 (12)	−0.0002 (12)
C4	0.0435 (14)	0.0466 (15)	0.0398 (14)	0.0068 (11)	0.0154 (12)	−0.0027 (11)
C6	0.0517 (16)	0.0551 (16)	0.0305 (13)	0.0116 (13)	0.0101 (12)	−0.0063 (11)
C3	0.0498 (15)	0.0503 (15)	0.0327 (13)	0.0049 (12)	0.0146 (12)	−0.0052 (11)
C5	0.0527 (16)	0.0673 (19)	0.0316 (14)	0.0177 (14)	0.0048 (12)	−0.0024 (13)
N2	0.075 (2)	0.0681 (19)	0.075 (2)	0.0103 (15)	0.0332 (17)	0.0024 (15)
C9	0.0572 (17)	0.0594 (18)	0.0343 (15)	0.0063 (14)	0.0137 (13)	0.0022 (12)

O1—C10	1.269 (3)	C8—C7	1.330 (4)
O2—C10	1.249 (3)	C8—N2	1.358 (4)
O2—H2	0.8200	C8—H8	0.9300
C1—C6	1.387 (4)	C7—H7	0.9300
C1—C2	1.396 (4)	C4—C3	1.386 (4)
C1—C10	1.502 (4)	C4—C5	1.391 (4)
N1—C7	1.313 (4)	C6—C5	1.376 (4)
N1—C9	1.367 (4)	C6—H6	0.9300
N1—H1	0.8600	C3—H3A	0.9300
O3—C4	1.357 (3)	C5—H5	0.9300
O3—H3	0.8200	N2—C9	1.341 (4)
C2—C3	1.381 (4)	C9—H9	0.9300
C2—H2A	0.9300
C10—O2—H2	109.5	N1—C7—H7	125.9
C6—C1—C2	118.0 (2)	C8—C7—H7	125.9
C6—C1—C10	120.8 (2)	O3—C4—C3	123.1 (2)
C2—C1—C10	121.2 (2)	O3—C4—C5	117.4 (2)
C7—N1—C9	108.7 (2)	C3—C4—C5	119.4 (2)
C7—N1—H1	125.7	C5—C6—C1	121.5 (2)
C9—N1—H1	125.7	C5—C6—H6	119.3
O2—C10—O1	122.8 (2)	C1—C6—H6	119.3
O2—C10—C1	118.9 (2)	C2—C3—C4	120.1 (2)
O1—C10—C1	118.3 (2)	C2—C3—H3A	119.9
C4—O3—H3	109.5	C4—C3—H3A	119.9
C3—C2—C1	121.0 (2)	C6—C5—C4	119.9 (3)
C3—C2—H2A	119.5	C6—C5—H5	120.0
C1—C2—H2A	119.5	C4—C5—H5	120.0
C7—C8—N2	108.9 (2)	C9—N2—C8	106.8 (3)
C7—C8—H8	125.6	N2—C9—N1	107.3 (3)
N2—C8—H8	125.6	N2—C9—H9	126.3
N1—C7—C8	108.2 (2)	N1—C9—H9	126.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.527	3.057 (3)	120.73
N1—H1···O2	0.86	1.818	2.678 (3)	177.32
O3—H3···O1i	0.82	1.831	2.635 (3)	166.35
C8—H8···O1ii	0.93	1.886	2.748 (3)	153.18

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.53	3.057 (3)	121
N1—H1⋯O2	0.86	1.82	2.678 (3)	177
O3—H3⋯O1i	0.82	1.83	2.635 (3)	166
C8—H8⋯O1ii	0.93	1.89	2.748 (3)	153

Symmetry codes: (i) ; (ii) .