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

Czapik, A.; Gdaniec, M.

doi:10.1107/S1600536808010568

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o895

doi:10.1107/S1600536808010568

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

Agnieszka Czapik ^a and Maria Gdaniec ^a ^*

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

(Received 3 April 2008; accepted 16 April 2008; online 23 April 2008)

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
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 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England.]$ ) T_min = 0.966, T_max = 1.000 (expected range = 0.960–0.994)
16706 measured reflections
3620 independent reflections
2285 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(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
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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)
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.

Supporting information

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

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

checkCIF report

Comment top

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].

Related literature top

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 top

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.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. : The molecular structure of the title compound with displacement ellipsoids shown at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. : Crystal packing viewed down the y axis. Hydrogen bonds are shown with dashed lines.
	Fig. 3. a) the H₂O helix with the 3-aminophenol molecules attached to the helix via hydrogen bonds to the amino group, b) two-dimensional polymeric structure formed by hydrogen-bonded quinoxaline A molecules and water molecules.

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

Crystal data top

2C₈H₆N₂·C₆H₇NO·2H₂O	F(000) = 856
M_r = 405.45	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5665 reflections
a = 15.2951 (10) Å	θ = 2.1–27.9°
b = 7.1383 (4) Å	µ = 0.09 mm⁻¹
c = 20.1614 (14) Å	T = 130 K
β = 110.775 (8)°	Plate, colourless
V = 2058.1 (3) Å³	0.40 × 0.40 × 0.07 mm
Z = 4

Data collection top

Kuma KM-4-CCD κ-geometry diffractometer	3620 independent reflections
Radiation source: fine-focus sealed tube	2285 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 25.0°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −18→17
T_min = 0.966, T_max = 1.000	k = −8→8
16706 measured reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0362P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max = 0.001
3620 reflections	Δρ_max = 0.20 e Å⁻³
300 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (5)

Crystal data top

2C₈H₆N₂·C₆H₇NO·2H₂O	V = 2058.1 (3) Å³
M_r = 405.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.2951 (10) Å	µ = 0.09 mm⁻¹
b = 7.1383 (4) Å	T = 130 K
c = 20.1614 (14) Å	0.40 × 0.40 × 0.07 mm
β = 110.775 (8)°

Data collection top

Kuma KM-4-CCD κ-geometry diffractometer	3620 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2285 reflections with I > 2σ(I)
T_min = 0.966, T_max = 1.000	R_int = 0.037
16706 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.20 e Å⁻³
3620 reflections	Δρ_min = −0.14 e Å⁻³
300 parameters

Special details top

Experimental. Absorption correction: SCALE3 ABSPACK scaling algorithm of the Crysalis RED program (Oxford Diffraction, 2007)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.40385 (8)	0.19751 (16)	0.55810 (6)	0.0257 (3)
C2A	0.33478 (10)	0.1595 (2)	0.49872 (7)	0.0268 (4)
H2A	0.2767	0.1284	0.5008	0.032*
C3A	0.34523 (10)	0.1639 (2)	0.43241 (8)	0.0272 (4)
H3A	0.2937	0.1354	0.3923	0.033*
N4A	0.42444 (8)	0.20642 (17)	0.42434 (6)	0.0257 (3)
C5A	0.58438 (10)	0.3015 (2)	0.48061 (8)	0.0295 (4)
H5A	0.5917	0.3043	0.4368	0.035*
C6A	0.65726 (10)	0.3465 (2)	0.54049 (9)	0.0346 (4)
H6A	0.7144	0.3799	0.5373	0.042*
C7A	0.64723 (10)	0.3431 (2)	0.60726 (8)	0.0346 (4)
H7A	0.6977	0.3744	0.6477	0.042*
C8A	0.56397 (10)	0.2943 (2)	0.61310 (8)	0.0295 (4)
H8A	0.5578	0.2925	0.6574	0.035*
C9A	0.48741 (9)	0.24661 (19)	0.55196 (7)	0.0223 (3)
C10A	0.49775 (9)	0.25055 (19)	0.48513 (7)	0.0215 (3)
N1B	−0.01606 (8)	0.88628 (16)	0.35287 (6)	0.0237 (3)
C2B	−0.10425 (10)	0.88544 (19)	0.34628 (7)	0.0257 (4)
H2B	−0.1194	0.8923	0.3870	0.031*
C3B	−0.17739 (10)	0.8745 (2)	0.27975 (8)	0.0294 (4)
H3B	−0.2388	0.8749	0.2785	0.035*
N4B	−0.16252 (8)	0.86390 (17)	0.21969 (6)	0.0297 (3)
C5B	−0.04863 (11)	0.8530 (2)	0.16312 (7)	0.0312 (4)
H5B	−0.0964	0.8453	0.1191	0.037*
C6B	0.04198 (11)	0.8538 (2)	0.16717 (8)	0.0333 (4)
H6B	0.0558	0.8487	0.1259	0.040*
C7B	0.11481 (11)	0.8625 (2)	0.23343 (8)	0.0331 (4)
H7B	0.1766	0.8617	0.2357	0.040*
C8B	0.09583 (10)	0.8720 (2)	0.29450 (8)	0.0294 (4)
H8B	0.1445	0.8775	0.3381	0.035*
C9B	0.00272 (9)	0.87338 (19)	0.29139 (7)	0.0210 (3)
C10B	−0.07063 (10)	0.86356 (19)	0.22497 (7)	0.0229 (3)
C1C	0.15035 (9)	0.7993 (2)	0.52107 (7)	0.0208 (3)
O1C	0.11852 (7)	0.96292 (14)	0.48513 (5)	0.0286 (3)
H1C	0.0737 (11)	0.936 (2)	0.4413 (9)	0.061 (6)*
C2C	0.22485 (9)	0.8116 (2)	0.58454 (7)	0.0217 (3)
H2C	0.2511	0.9280	0.6007	0.026*
C3C	0.26114 (9)	0.6520 (2)	0.62471 (7)	0.0240 (4)
N1C	0.33268 (10)	0.6689 (2)	0.68974 (8)	0.0443 (4)
H2NC	0.3584 (10)	0.561 (2)	0.7146 (8)	0.044 (5)*
H1NC	0.3613 (10)	0.780 (2)	0.6997 (8)	0.037 (5)*
C4C	0.22258 (9)	0.4776 (2)	0.59862 (7)	0.0274 (4)
H4C	0.2472	0.3690	0.6238	0.033*
C5C	0.14761 (10)	0.4673 (2)	0.53511 (7)	0.0268 (4)
H5C	0.1218	0.3509	0.5183	0.032*
C6C	0.11020 (9)	0.6262 (2)	0.49608 (7)	0.0249 (4)
H6C	0.0592	0.6176	0.4539	0.030*
O1D	0.40947 (7)	0.06594 (16)	0.69381 (7)	0.0325 (3)
H1D	0.4028 (12)	0.121 (3)	0.6539 (11)	0.071 (7)*
H2D	0.4209 (13)	0.161 (3)	0.7281 (11)	0.089 (8)*
O1E	0.43284 (8)	0.14985 (16)	0.28706 (6)	0.0320 (3)
H1E	0.4870 (14)	0.078 (3)	0.2927 (10)	0.086 (7)*
H2E	0.4315 (12)	0.175 (3)	0.3316 (11)	0.077 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0264 (7)	0.0255 (8)	0.0254 (7)	−0.0008 (5)	0.0097 (6)	0.0018 (5)
C2A	0.0243 (8)	0.0269 (10)	0.0292 (9)	−0.0017 (7)	0.0095 (7)	0.0011 (7)
C3A	0.0255 (9)	0.0251 (10)	0.0263 (9)	−0.0008 (7)	0.0036 (7)	−0.0005 (7)
N4A	0.0280 (7)	0.0239 (7)	0.0249 (7)	0.0011 (5)	0.0090 (6)	0.0006 (5)
C5A	0.0293 (9)	0.0268 (10)	0.0378 (10)	0.0035 (7)	0.0185 (8)	0.0019 (7)
C6A	0.0228 (9)	0.0256 (10)	0.0568 (12)	−0.0007 (7)	0.0158 (8)	−0.0005 (8)
C7A	0.0274 (9)	0.0274 (10)	0.0396 (10)	0.0002 (7)	0.0001 (8)	−0.0030 (8)
C8A	0.0312 (9)	0.0283 (9)	0.0253 (9)	−0.0006 (7)	0.0054 (7)	−0.0015 (7)
C9A	0.0239 (8)	0.0169 (9)	0.0256 (9)	0.0009 (6)	0.0083 (7)	0.0018 (6)
C10A	0.0247 (8)	0.0155 (9)	0.0248 (9)	0.0030 (6)	0.0094 (7)	0.0005 (6)
N1B	0.0234 (7)	0.0231 (8)	0.0242 (7)	0.0012 (5)	0.0078 (6)	0.0024 (5)
C2B	0.0298 (9)	0.0242 (9)	0.0269 (9)	0.0032 (7)	0.0146 (7)	0.0049 (7)
C3B	0.0218 (8)	0.0331 (10)	0.0348 (10)	0.0012 (7)	0.0120 (7)	0.0063 (7)
N4B	0.0254 (7)	0.0345 (9)	0.0283 (7)	0.0002 (6)	0.0083 (6)	0.0050 (6)
C5B	0.0410 (10)	0.0298 (10)	0.0233 (9)	0.0000 (7)	0.0120 (8)	0.0015 (7)
C6B	0.0486 (11)	0.0281 (10)	0.0331 (10)	0.0024 (8)	0.0266 (8)	0.0046 (7)
C7B	0.0314 (9)	0.0270 (10)	0.0492 (11)	0.0029 (7)	0.0246 (8)	0.0043 (8)
C8B	0.0233 (9)	0.0296 (10)	0.0339 (9)	0.0026 (7)	0.0084 (7)	0.0029 (7)
C9B	0.0241 (8)	0.0164 (8)	0.0235 (8)	0.0019 (6)	0.0099 (7)	0.0027 (6)
C10B	0.0261 (8)	0.0183 (9)	0.0247 (8)	0.0013 (6)	0.0093 (7)	0.0038 (6)
C1C	0.0210 (8)	0.0218 (9)	0.0215 (8)	0.0031 (7)	0.0100 (7)	0.0026 (7)
O1C	0.0286 (6)	0.0246 (7)	0.0255 (6)	−0.0010 (5)	0.0009 (5)	0.0019 (5)
C2C	0.0192 (8)	0.0232 (9)	0.0239 (8)	−0.0042 (6)	0.0088 (6)	−0.0024 (6)
C3C	0.0173 (8)	0.0311 (10)	0.0243 (8)	−0.0010 (7)	0.0082 (7)	0.0038 (7)
N1C	0.0365 (9)	0.0366 (10)	0.0408 (9)	−0.0100 (8)	−0.0099 (7)	0.0144 (8)
C4C	0.0256 (9)	0.0270 (10)	0.0314 (9)	0.0025 (7)	0.0124 (7)	0.0085 (7)
C5C	0.0298 (9)	0.0236 (9)	0.0294 (9)	−0.0049 (7)	0.0136 (7)	−0.0030 (7)
C6C	0.0244 (8)	0.0272 (10)	0.0221 (8)	−0.0031 (7)	0.0069 (7)	−0.0014 (7)
O1D	0.0400 (7)	0.0326 (7)	0.0252 (7)	−0.0059 (5)	0.0119 (5)	−0.0024 (6)
O1E	0.0382 (7)	0.0348 (7)	0.0229 (6)	0.0000 (5)	0.0106 (5)	0.0005 (5)

Geometric parameters (Å, º) top

N1A—C2A	1.3136 (16)	C6B—C7B	1.405 (2)
N1A—C9A	1.3725 (17)	C6B—H6B	0.9300
C2A—C3A	1.402 (2)	C7B—C8B	1.363 (2)
C2A—H2A	0.9300	C7B—H7B	0.9300
C3A—N4A	1.3138 (17)	C8B—C9B	1.4031 (18)
C3A—H3A	0.9300	C8B—H8B	0.9300
N4A—C10A	1.3726 (16)	C9B—C10B	1.4111 (18)
C5A—C6A	1.3597 (19)	C1C—O1C	1.3697 (16)
C5A—C10A	1.4078 (18)	C1C—C2C	1.3818 (17)
C5A—H5A	0.9300	C1C—C6C	1.3919 (19)
C6A—C7A	1.408 (2)	O1C—H1C	0.927 (17)
C6A—H6A	0.9300	C2C—C3C	1.3940 (19)
C7A—C8A	1.365 (2)	C2C—H2C	0.9300
C7A—H7A	0.9300	C3C—N1C	1.3832 (18)
C8A—C9A	1.4080 (18)	C3C—C4C	1.398 (2)
C8A—H8A	0.9300	N1C—H2NC	0.927 (16)
C9A—C10A	1.4116 (19)	N1C—H1NC	0.891 (16)
N1B—C2B	1.3077 (16)	C4C—C5C	1.3850 (18)
N1B—C9B	1.3711 (17)	C4C—H4C	0.9300
C2B—C3B	1.4114 (19)	C5C—C6C	1.3839 (19)
C2B—H2B	0.9300	C5C—H5C	0.9300
C3B—N4B	1.3112 (18)	C6C—H6C	0.9300
C3B—H3B	0.9300	O1D—H1D	0.87 (2)
N4B—C10B	1.3714 (16)	O1D—H2D	0.94 (2)
C5B—C6B	1.3591 (19)	O1E—H1E	0.95 (2)
C5B—C10B	1.404 (2)	O1E—H2E	0.92 (2)
C5B—H5B	0.9300

C2A—N1A—C9A	116.37 (12)	C5B—C6B—H6B	119.8
N1A—C2A—C3A	122.51 (14)	C7B—C6B—H6B	119.8
N1A—C2A—H2A	118.7	C8B—C7B—C6B	120.66 (14)
C3A—C2A—H2A	118.7	C8B—C7B—H7B	119.7
N4A—C3A—C2A	123.05 (13)	C6B—C7B—H7B	119.7
N4A—C3A—H3A	118.5	C7B—C8B—C9B	119.86 (14)
C2A—C3A—H3A	118.5	C7B—C8B—H8B	120.1
C3A—N4A—C10A	116.07 (12)	C9B—C8B—H8B	120.1
C6A—C5A—C10A	119.83 (15)	N1B—C9B—C8B	119.66 (12)
C6A—C5A—H5A	120.1	N1B—C9B—C10B	120.68 (12)
C10A—C5A—H5A	120.1	C8B—C9B—C10B	119.65 (13)
C5A—C6A—C7A	120.79 (15)	N4B—C10B—C5B	119.54 (13)
C5A—C6A—H6A	119.6	N4B—C10B—C9B	121.44 (13)
C7A—C6A—H6A	119.6	C5B—C10B—C9B	119.02 (13)
C8A—C7A—C6A	120.54 (14)	O1C—C1C—C2C	117.20 (13)
C8A—C7A—H7A	119.7	O1C—C1C—C6C	122.48 (12)
C6A—C7A—H7A	119.7	C2C—C1C—C6C	120.32 (13)
C7A—C8A—C9A	119.86 (14)	C1C—O1C—H1C	109.2 (11)
C7A—C8A—H8A	120.1	C1C—C2C—C3C	120.90 (13)
C9A—C8A—H8A	120.1	C1C—C2C—H2C	119.6
N1A—C9A—C8A	119.65 (13)	C3C—C2C—H2C	119.6
N1A—C9A—C10A	120.96 (12)	N1C—C3C—C2C	119.84 (14)
C8A—C9A—C10A	119.40 (13)	N1C—C3C—C4C	121.36 (14)
N4A—C10A—C5A	119.40 (13)	C2C—C3C—C4C	118.78 (13)
N4A—C10A—C9A	121.01 (13)	C3C—N1C—H2NC	118.7 (10)
C5A—C10A—C9A	119.59 (13)	C3C—N1C—H1NC	116.8 (10)
C2B—N1B—C9B	116.56 (11)	H2NC—N1C—H1NC	122.4 (14)
N1B—C2B—C3B	122.56 (14)	C5C—C4C—C3C	119.71 (13)
N1B—C2B—H2B	118.7	C5C—C4C—H4C	120.1
C3B—C2B—H2B	118.7	C3C—C4C—H4C	120.1
N4B—C3B—C2B	122.83 (14)	C6C—C5C—C4C	121.45 (14)
N4B—C3B—H3B	118.6	C6C—C5C—H5C	119.3
C2B—C3B—H3B	118.6	C4C—C5C—H5C	119.3
C3B—N4B—C10B	115.92 (12)	C5C—C6C—C1C	118.79 (13)
C6B—C5B—C10B	120.46 (14)	C5C—C6C—H6C	120.6
C6B—C5B—H5B	119.8	C1C—C6C—H6C	120.6
C10B—C5B—H5B	119.8	H1D—O1D—H2D	106.6 (18)
C5B—C6B—C7B	120.34 (14)	H1E—O1E—H2E	107.9 (16)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	2C₈H₆N₂·C₆H₇NO·2H₂O
M_r	405.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	130
a, b, c (Å)	15.2951 (10), 7.1383 (4), 20.1614 (14)
β (°)	110.775 (8)
V (Å³)	2058.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.40 × 0.07

Data collection
Diffractometer	Kuma KM-4-CCD κ-geometry diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.966, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16706, 3620, 2285
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.070, 0.91
No. of reflections	3620
No. of parameters	300
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z; (iii) −x+1, −y, −z+1.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kadzewski, A. & Gdaniec, M. (2006). Acta Cryst. E62, o3498–o3500. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sokolov, A. N., Friščić, T., Blais, S., Ripmeester, J. A. & MacGillivray, L. R. (2006). Cryst. Growth Des. 6, 2427–2428. Web of Science CSD CrossRef CAS Google Scholar
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Thalladi, V. R., Smolka, T., Boese, R. & Sustmann, R. (2000). CrystEngComm, 2, 96–101. Web of Science CSD CrossRef Google Scholar

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Volume 64| Part 5| May 2008| Page o895

doi:10.1107/S1600536808010568

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