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

Czapik, A.; Gdaniec, M.

doi:10.1107/S1600536808010568

Volume 64
Part 5
Page o895
May 2008

Received 3 April 2008
Accepted 16 April 2008
Online 23 April 2008

Key indicators
Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.070
Data-to-parameter ratio = 12.1
Details

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

Agnieszka Czapik ^a and Maria Gdaniec ^a ^*

^aFaculty of Chemistry, Adam Mickiewicz University, 60-780 Poznan, Poland
Correspondence e-mail: magdan@amu.edu.pl

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, P 2₁ /c
a = 15.2951 (10) Å
b = 7.1383 (4) Å
c = 20.1614 (14) Å
= 110.775 (8)°
V = 2058.1 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 130.0 (2) K
0.40 × 0.40 × 0.07 mm

Data collection

Kuma KM-4-CCD -geometry diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ) T_min = 0.966, T_max = 1.000 (expected range = 0.960-0.994)
16706 measured reflections
3620 independent reflections
2285 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.070
S = 0.91
3620 reflections
300 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1C-H1CN1B	0.927 (17)	1.857 (17)	2.7844 (14)	178.7 (16)
N1C-H2NCO1Eⁱ	0.927 (16)	2.125 (17)	3.0400 (19)	168.8 (14)
N1C-H1NCO1Dⁱⁱ	0.891 (16)	2.191 (17)	3.058 (2)	164.4 (13)
O1D-H1DN1A	0.87 (2)	2.01 (2)	2.8651 (17)	166.8 (17)
O1D-H2DO1Eⁱ	0.94 (2)	1.77 (2)	2.7022 (16)	174.5 (19)
O1E-H1EO1Dⁱⁱⁱ	0.95 (2)	1.82 (2)	2.7711 (17)	177.8 (19)
O1E-H2EN4A	0.92 (2)	1.92 (2)	2.8446 (16)	175.4 (18)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) -x+1, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: FL2194 ).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kadzewski, A. & Gdaniec, M. (2006). Acta Cryst. E62, o3498-o3500.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sokolov, A. N., Friscic, T., Blais, S., Ripmeester, J. A. & MacGillivray, L. R. (2006). Cryst. Growth Des. 6, 2427-2428.
Sokolov, A. N. & MacGillivray, L. R. (2006). Cryst. Growth Des. 6, 2615-2624.
Thalladi, V. R., Smolka, T., Boese, R. & Sustmann, R. (2000). CrystEngComm, 2, 96-101.

organic compounds