Phenazine-naphthalene-1,5-diamine-water (1/1/2).

The asymmetric unit of the title compound, C(12)H(8)N(2)·C(10)H(10)N(2)·2H(2)O, contains one half-mol-ecule of phenazine, one half-mol-ecule of naphthalene-1,5-diamine and one water mol-ecule. The phenazine and naphthalene-1,5-diamine mol-ecules are located on inversion centers. The water mol-ecules serve as bridges between the naphthalene-1,5-diamine mol-ecules and also between the naphthalene-1,5-diamine and phenazine mol-ecules. The naphthalene-1,5-diamine and water mol-ecules are connected via N-H⋯O and O-H⋯N hydrogen bonds, forming a T4(2) motif. They are arranged into a two-dimensional polymeric structure parallel to (10) in which the water mol-ecule is a single donor and a double acceptor, whereas the amino group is a double donor and a single acceptor in the hydrogen bonding. These two-dimensional assemblies alternate with the layers of phenazine mol-ecules arranged into a herringbone motif. Each phenazine mol-ecule is hydrogen bonded to two water mol-ecules and thus a three-dimensional framework of hydrogen-bonded mol-ecules is generated.

Related literature

For the structures of co-crystals of aromatic diaza­heterocycles with small aromatic mol­ecules, see: Thalladi et al. (2000 ▶); Kadzewski & Gdaniec (2006 ▶); Czapik & Gdaniec (2008 ▶). For structures with similar T4(2) hydrogen-bond motifs, see: Anthony et al. (2007 ▶); Neely et al. (2007 ▶). For symbols of hydrogen-bond motifs, see: Infantes et al. (2003 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C12H8N2·C10H10N2·2H2O

M = 374.44

Monoclinic,

a = 13.0395 (10) Å

b = 4.9266 (2) Å

c = 15.7211 (12) Å

β = 112.508 (9)°

V = 933.00 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 130 K

0.25 × 0.25 × 0.25 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer

Absorption correction: none

5251 measured reflections

1643 independent reflections

1357 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 1.08

1643 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.23 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049009/rz2392sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049009/rz2392Isup2.hkl

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

C12H8N2·C10H10N2·2H2O	F(000) = 396
Mr = 374.44	Dx = 1.333 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3369 reflections
a = 13.0395 (10) Å	θ = 2.6–27.9°
b = 4.9266 (2) Å	µ = 0.09 mm−1
c = 15.7211 (12) Å	T = 130 K
β = 112.508 (9)°	Cube, red
V = 933.00 (11) Å3	0.25 × 0.25 × 0.25 mm
Z = 2

Kuma KM-4-CCD κ-geometry diffractometer	1357 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 25.0°, θmin = 4.4°
ω scans	h = −15→15
5251 measured reflections	k = −5→5
1643 independent reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0606P)2 + 1.1003P] where P = (Fo2 + 2Fc2)/3
1643 reflections	(Δ/σ)max < 0.001
143 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.23 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
N1A	0.12558 (17)	0.2658 (5)	0.18906 (13)	0.0249 (5)
H1N	0.116 (3)	0.419 (8)	0.218 (2)	0.054 (10)*
H2N	0.198 (3)	0.258 (6)	0.1847 (19)	0.038 (8)*
C1A	0.03659 (18)	0.2272 (5)	0.10357 (15)	0.0220 (5)
C2A	−0.05954 (19)	0.3753 (5)	0.08078 (15)	0.0245 (5)
H2A	−0.0655	0.5056	0.1214	0.029*
C3A	−0.14918 (19)	0.3314 (5)	−0.00367 (16)	0.0248 (5)
H3A	−0.2135	0.4343	−0.0185	0.030*
C4A	0.14256 (19)	−0.1391 (5)	0.06406 (16)	0.0243 (5)
H4A	0.2021	−0.1134	0.1197	0.029*
C5A	0.04549 (18)	0.0218 (5)	0.04242 (15)	0.0223 (5)
N1B	0.05503 (15)	0.9466 (4)	0.43964 (12)	0.0220 (5)
C2B	0.08133 (18)	0.8115 (5)	0.51930 (15)	0.0211 (5)
C3B	0.16597 (18)	0.6111 (5)	0.54398 (16)	0.0252 (5)
H3B	0.2031	0.5753	0.5051	0.030*
C4B	0.19301 (19)	0.4712 (5)	0.62413 (17)	0.0279 (6)
H4B	0.2489	0.3411	0.6399	0.033*
C5B	−0.02539 (18)	1.1344 (5)	0.41932 (15)	0.0217 (5)
C6B	−0.0560 (2)	1.2869 (5)	0.33626 (15)	0.0258 (6)
H6B	−0.0206	1.2553	0.2959	0.031*
C7B	−0.1367 (2)	1.4781 (5)	0.31585 (16)	0.0290 (6)
H7B	−0.1555	1.5778	0.2617	0.035*
O1W	0.12857 (15)	0.7813 (4)	0.29145 (12)	0.0297 (5)
H1W	0.137 (3)	0.932 (10)	0.269 (3)	0.074 (13)*
H2W	0.107 (2)	0.819 (6)	0.337 (2)	0.035 (8)*

	U11	U22	U33	U12	U13	U23
N1A	0.0267 (11)	0.0260 (12)	0.0211 (10)	−0.0033 (9)	0.0081 (8)	−0.0025 (9)
C1A	0.0246 (12)	0.0221 (12)	0.0212 (11)	−0.0043 (10)	0.0108 (9)	0.0018 (9)
C2A	0.0294 (12)	0.0227 (12)	0.0247 (12)	−0.0004 (10)	0.0138 (10)	0.0008 (10)
C3A	0.0222 (11)	0.0244 (13)	0.0292 (12)	0.0022 (10)	0.0114 (10)	0.0043 (10)
C4A	0.0223 (11)	0.0243 (13)	0.0261 (12)	−0.0029 (10)	0.0089 (9)	0.0011 (10)
C5A	0.0261 (11)	0.0201 (12)	0.0240 (11)	−0.0036 (9)	0.0132 (10)	0.0020 (9)
N1B	0.0252 (10)	0.0201 (10)	0.0230 (10)	−0.0026 (8)	0.0119 (8)	−0.0032 (8)
C2B	0.0226 (11)	0.0181 (12)	0.0247 (11)	−0.0044 (9)	0.0114 (9)	−0.0038 (9)
C3B	0.0245 (12)	0.0240 (12)	0.0302 (12)	−0.0001 (10)	0.0139 (10)	−0.0017 (10)
C4B	0.0250 (12)	0.0216 (13)	0.0346 (13)	0.0027 (10)	0.0085 (10)	−0.0008 (10)
C5B	0.0228 (11)	0.0196 (12)	0.0246 (12)	−0.0039 (9)	0.0111 (9)	−0.0040 (9)
C6B	0.0312 (12)	0.0262 (13)	0.0220 (12)	−0.0006 (11)	0.0124 (10)	−0.0005 (10)
C7B	0.0355 (13)	0.0237 (13)	0.0257 (12)	−0.0014 (11)	0.0094 (10)	0.0021 (10)
O1W	0.0405 (10)	0.0279 (11)	0.0257 (9)	0.0042 (8)	0.0182 (8)	−0.0001 (8)

N1A—C1A	1.412 (3)	N1B—C5B	1.342 (3)
N1A—H1N	0.91 (4)	C2B—C3B	1.420 (3)
N1A—H2N	0.97 (3)	C2B—C5Bii	1.440 (3)
C1A—C2A	1.374 (3)	C3B—C4B	1.359 (3)
C1A—C5A	1.431 (3)	C3B—H3B	0.9300
C2A—C3A	1.410 (3)	C4B—C7Bii	1.422 (4)
C2A—H2A	0.9300	C4B—H4B	0.9300
C3A—C4Ai	1.367 (3)	C5B—C6B	1.425 (3)
C3A—H3A	0.9300	C6B—C7B	1.356 (3)
C4A—C3Ai	1.367 (3)	C6B—H6B	0.9300
C4A—C5A	1.420 (3)	C7B—H7B	0.9300
C4A—H4A	0.9300	O1W—H1W	0.85 (5)
C5A—C5Ai	1.422 (4)	O1W—H2W	0.89 (3)
N1B—C2B	1.341 (3)
C1A—N1A—H1N	111 (2)	N1B—C2B—C3B	119.61 (19)
C1A—N1A—H2N	113.2 (16)	N1B—C2B—C5Bii	121.3 (2)
H1N—N1A—H2N	113 (3)	C3B—C2B—C5Bii	119.1 (2)
C2A—C1A—N1A	120.8 (2)	C4B—C3B—C2B	120.3 (2)
C2A—C1A—C5A	120.1 (2)	C4B—C3B—H3B	119.8
N1A—C1A—C5A	119.1 (2)	C2B—C3B—H3B	119.8
C1A—C2A—C3A	120.6 (2)	C3B—C4B—C7Bii	120.7 (2)
C1A—C2A—H2A	119.7	C3B—C4B—H4B	119.7
C3A—C2A—H2A	119.7	C7Bii—C4B—H4B	119.7
C4Ai—C3A—C2A	120.7 (2)	N1B—C5B—C6B	120.1 (2)
C4Ai—C3A—H3A	119.7	N1B—C5B—C2Bii	121.2 (2)
C2A—C3A—H3A	119.7	C6B—C5B—C2Bii	118.7 (2)
C3Ai—C4A—C5A	120.5 (2)	C7B—C6B—C5B	120.2 (2)
C3Ai—C4A—H4A	119.7	C7B—C6B—H6B	119.9
C5A—C4A—H4A	119.7	C5B—C6B—H6B	119.9
C4A—C5A—C5Ai	119.2 (3)	C6B—C7B—C4Bii	121.0 (2)
C4A—C5A—C1A	121.9 (2)	C6B—C7B—H7B	119.5
C5Ai—C5A—C1A	118.9 (3)	C4Bii—C7B—H7B	119.5
C2B—N1B—C5B	117.47 (18)	H1W—O1W—H2W	107 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1N···O1W	0.91 (4)	2.10 (4)	2.999 (3)	169 (3)
N1A—H2N···O1Wiii	0.97 (3)	2.15 (3)	3.102 (3)	166 (2)
O1W—H1W···N1Aiv	0.85 (5)	2.04 (5)	2.871 (3)	167 (4)
O1W—H2W···N1B	0.89 (3)	2.07 (3)	2.953 (3)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1N⋯O1W	0.91 (4)	2.10 (4)	2.999 (3)	169 (3)
N1A—H2N⋯O1W i	0.97 (3)	2.15 (3)	3.102 (3)	166 (2)
O1W—H1W⋯N1A ii	0.85 (5)	2.04 (5)	2.871 (3)	167 (4)
O1W—H2W⋯N1B	0.89 (3)	2.07 (3)	2.953 (3)	174 (3)

Symmetry codes: (i) ; (ii) .