Quinoxaline–3-amino­phenol–water (2/1/2)

Agnieszka Czapik; Maria Gdaniec

doi:10.1107/S1600536808010568

. 2008 Apr 23;64(Pt 5):o895. doi: 10.1107/S1600536808010568

Quinoxaline–3-aminophenol–water (2/1/2)

Agnieszka Czapik ^a, Maria Gdaniec ^a,^*

PMCID: PMC2961097 PMID: 21202378

Abstract

The asymmetric unit of the title compound, 2C₈H₆N₂·C₆H₇NO·2H₂O, contains two quinoxaline molecules, one molecule of 3-aminophenol and two water molecules which are hydrogen bonded to form a two-dimensional polymeric structure. Each of the symmetry-independent quinoxaline molecules forms separate stacks of different symmetry. In one set of stacks, the molecules are related by a screw axis and are slightly tilted [dihedral angle = 7.12 (1)°]. In the second set of stacks, adjacent molecules are parallel and related by an inversion center [interplanar distances = 3.376 (4) and 3.473 (4) Å].

Related literature

For supramolecular ladders, see: Sokolov & MacGillivray (2006 ▶); Sokolov et al. (2006 ▶). For complexes of aromatic diazaheterocycles with phenols, see: Thalladi et al. (2000 ▶); Kadzewski & Gdaniec (2006 ▶).

Experimental

Crystal data

2C₈H₆N₂·C₆H₇NO·2H₂O
M _r = 405.45
Monoclinic,
a = 15.2951 (10) Å
b = 7.1383 (4) Å
c = 20.1614 (14) Å
β = 110.775 (8)°
V = 2058.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 130.0 (2) K
0.40 × 0.40 × 0.07 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.966, T _max = 1.000 (expected range = 0.960–0.994)
16706 measured reflections
3620 independent reflections
2285 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.070
S = 0.91
3620 reflections
300 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010568/fl2194sup1.cif

e-64-0o895-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010568/fl2194Isup2.hkl

e-64-0o895-Isup2.hkl^{(177.5KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1C—H1C⋯N1B	0.927 (17)	1.857 (17)	2.7844 (14)	178.7 (16)
N1C—H2NC⋯O1Eⁱ	0.927 (16)	2.125 (17)	3.0400 (19)	168.8 (14)
N1C—H1NC⋯O1Dⁱⁱ	0.891 (16)	2.191 (17)	3.058 (2)	164.4 (13)
O1D—H1D⋯N1A	0.87 (2)	2.01 (2)	2.8651 (17)	166.8 (17)
O1D—H2D⋯O1Eⁱ	0.94 (2)	1.77 (2)	2.7022 (16)	174.5 (19)
O1E—H1E⋯O1Dⁱⁱⁱ	0.95 (2)	1.82 (2)	2.7711 (17)	177.8 (19)
O1E—H2E⋯N4A	0.92 (2)	1.92 (2)	2.8446 (16)	175.4 (18)

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

supplementary crystallographic information

Comment

3-Aminophenol shows the ability to direct the assembly of supramolecular ladders via hydrogen bonding and π–π stacking interactions in the solid state (Sokolov et al., 2006; Sokolov & MacGillivray, 2006). On the other hand, heterocycles like phenazine and quinoxaline are known to form a robust host framework with one-dimensional channels filled with small aromatic guest molecules (Thalladi et al., 2000; Kadzewski & Gdaniec, 2006). In the course of our studies on molecular complexes of diazaaromatic heterocycles we cocrystallized quinoxaline with 3-aminophenol expecting to obtain ladder-type assemblies analogous to those observed in cocrystals of bipyridines with 3-aminophenol (Sokolov et al., 2006). Unfortunately, the molecular complex with the expected 2:1 component ratio crystallized as a dihydrate (Fig. 1) that had a significant impact on the organization of molecules in the crystal.

Crystal packing of the title compound is shown in Fig. 2. The asymmetric unit contains two quinoxaline molecules, one 3-aminophenol molecule and two water molecules. The water molecules are hydrogen-bonded (for the hydrogen-bond geometry see Table 2) to form a helix extending along the b axis with the amino group of the 3-aminophenol linked to the helix via N—H···O interactions in the manner shown in Fig. 3a. The quinoxaline B molecules join to this assembly via hydrogen bonds to the phenolic OH groups whereas the quinoxaline A molecules bridge the water helices via O—H···N bonding and π–π stacking interactions generating a supramolecular two dimensional polymeric structure (Figure 3 b). The quinoxaline B molecules are also organized into π–π stacks extending along the b axis. The B molecules in the stacks are related by a screw-axis and are slightly tilted [dihedral angle of 7.12 (1)°] whereas the A molecules are parallel and related by inversion centers [interplanar distances of 3.376 (4) and 3.473 (4) Å].

Experimental

The title compound was obtained by dissolving quinoxaline (0.2 g, 1.54 mmol) and 3-aminophenol (0.084 g, 0.77 mmol) in 5 ml of methanol followed slow evaporation to yield colorless plates suitable for data collection.