6-[(4-Hy-droxy-phen-yl)diazenyl]-1,10-phenanthrolin-1-ium chloride monohydrate.

In the cation of the title mol-ecular salt, C(18)H(13)N(4)O(+)·Cl(-)·H(2)O, the dihedral angle between the mean planes of the 1,10-phenanthroline system and the phenol ring is 14.40 (19)°. The crystal packing is stabilized by O-H⋯O hydrogen bonds, weak N-H⋯Cl and O-H⋯Cl inter-molecular inter-actions and π-π stacking inter-actions [centroid-centroid distance = 3.6944 (13) and 3.9702 (12) Å].

Related literature

For Ru(II)–polypyridyl complexes as solar energy conversion catalysts, see: Vos & Kelly (2006 ▶). For strongly absorbing Ru(II) complexes containing azo-dye ligands, see: McGuire et al. (1998 ▶); Malinowski & McGuire (2003 ▶); For the pKa of the phenol portion of these complexes, see: Zhang (1999 ▶). For the synthesis and characterization of 1,10-phenanthroline­azo­sulfonamide derivatives and their ternary Ni(II) complexes, see: Aly et al. (2006 ▶). For the synthesis of 5-nitro-1,10-phenanthroline, see: Amouyal et al. (1990 ▶) and of 5-amino-1,10-phenanthroline, see: Nasielski-Hinkens et al. (1981 ▶). For the crystal structure of 4-[(E)-1-naphthyl­diazen­yl]phenol, see: Aslanov et al. (2009 ▶) and of 2-pyridyl-diazo-1,3 phenol, see: Xu et al. (1982 ▶).

Experimental

Crystal data

C18H13N4O+·Cl−·H2O

M = 354.79

Triclinic,

a = 7.6732 (4) Å

b = 7.7894 (4) Å

c = 14.1225 (7) Å

α = 78.535 (3)°

β = 80.379 (3)°

γ = 78.212 (3)°

V = 802.73 (7) Å3

Z = 2

Cu Kα radiation

μ = 2.28 mm−1

T = 100 K

0.41 × 0.26 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.454, T max = 0.914

15401 measured reflections

2806 independent reflections

2407 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.03

2806 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044941/jj2106sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044941/jj2106Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044941/jj2106Isup3.mol

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

C18H13N4O+·Cl−·H2O	Z = 2
Mr = 354.79	F(000) = 368
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.6732 (4) Å	Cell parameters from 4384 reflections
b = 7.7894 (4) Å	θ = 3.2–66.7°
c = 14.1225 (7) Å	µ = 2.28 mm−1
α = 78.535 (3)°	T = 100 K
β = 80.379 (3)°	Transparent plate, orange
γ = 78.212 (3)°	0.41 × 0.26 × 0.04 mm
V = 802.73 (7) Å3

Bruker APEXII CCD diffractometer	2806 independent reflections
Radiation source: fine-focus sealed tube	2407 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 8.33 pixels mm-1	θmax = 67.4°, θmin = 3.2°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −7→9
Tmin = 0.454, Tmax = 0.914	l = −16→16
15401 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0805P)2 + 0.1676P] where P = (Fo2 + 2Fc2)/3
2806 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.21 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
Cl1	0.24720 (6)	0.24063 (6)	0.05019 (3)	0.02974 (18)
O1	0.8362 (2)	1.58116 (19)	−0.72107 (11)	0.0356 (4)
O2	0.0147 (2)	0.5892 (2)	0.10617 (11)	0.0319 (4)
N1	0.3212 (2)	0.6808 (2)	−0.09907 (12)	0.0286 (4)
N2	0.5247 (2)	0.3608 (2)	−0.12489 (13)	0.0278 (4)
N3	0.6421 (2)	0.9679 (2)	−0.39335 (12)	0.0289 (4)
N4	0.7403 (2)	0.9508 (2)	−0.47300 (12)	0.0288 (4)
C1	0.2241 (3)	0.8387 (3)	−0.08742 (15)	0.0301 (5)
H1	0.1353	0.8451	−0.0320	0.036*
C2	0.2451 (3)	0.9963 (3)	−0.15216 (16)	0.0307 (5)
H2	0.1716	1.1059	−0.1405	0.037*
C3	0.3723 (3)	0.9915 (3)	−0.23242 (15)	0.0289 (5)
H3	0.3878	1.0975	−0.2771	0.035*
C4	0.4799 (3)	0.8273 (3)	−0.24789 (14)	0.0265 (4)
C5	0.6165 (3)	0.8060 (3)	−0.33052 (14)	0.0272 (4)
C6	0.7152 (3)	0.6433 (3)	−0.34203 (15)	0.0281 (4)
H6	0.8043	0.6327	−0.3970	0.034*
C7	0.6860 (3)	0.4882 (3)	−0.27224 (15)	0.0277 (4)
C8	0.7851 (3)	0.3169 (3)	−0.27964 (15)	0.0302 (5)
H8	0.8755	0.3004	−0.3335	0.036*
C9	0.7517 (3)	0.1734 (3)	−0.20927 (16)	0.0314 (5)
H9	0.8194	0.0580	−0.2139	0.038*
C10	0.6177 (3)	0.1993 (3)	−0.13131 (15)	0.0298 (5)
H10	0.5928	0.1010	−0.0826	0.036*
C11	0.5531 (3)	0.5072 (3)	−0.19183 (14)	0.0263 (4)
C12	0.4470 (3)	0.6768 (3)	−0.17871 (14)	0.0258 (4)
C13	0.7674 (3)	1.1138 (3)	−0.53279 (15)	0.0273 (4)
C14	0.6952 (3)	1.2806 (3)	−0.50623 (16)	0.0337 (5)
H14	0.6267	1.2879	−0.4441	0.040*
C15	0.7232 (3)	1.4333 (3)	−0.56975 (16)	0.0344 (5)
H15	0.6758	1.5458	−0.5508	0.041*
C16	0.8206 (3)	1.4250 (3)	−0.66197 (15)	0.0302 (5)
C17	0.8979 (3)	1.2599 (3)	−0.68827 (15)	0.0283 (4)
H17	0.9682	1.2527	−0.7499	0.034*
C18	0.8705 (3)	1.1070 (3)	−0.62302 (15)	0.0284 (4)
H18	0.9236	0.9943	−0.6405	0.034*
H4	0.902 (4)	1.565 (4)	−0.783 (2)	0.052 (8)*
H19	0.442 (4)	0.377 (3)	−0.076 (2)	0.045 (7)*
H20	0.077 (4)	0.494 (4)	0.091 (2)	0.054 (8)*
H21	−0.055 (4)	0.622 (4)	0.062 (2)	0.050 (8)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0299 (3)	0.0235 (3)	0.0305 (3)	0.00016 (18)	−0.00177 (19)	0.00097 (18)
O1	0.0425 (9)	0.0243 (8)	0.0323 (8)	−0.0014 (6)	0.0041 (7)	0.0007 (6)
O2	0.0383 (9)	0.0256 (8)	0.0288 (8)	0.0005 (6)	−0.0038 (7)	−0.0041 (6)
N1	0.0299 (9)	0.0255 (9)	0.0280 (9)	−0.0050 (7)	−0.0016 (7)	−0.0011 (7)
N2	0.0282 (9)	0.0249 (9)	0.0272 (9)	−0.0021 (7)	−0.0023 (7)	−0.0013 (7)
N3	0.0283 (9)	0.0280 (9)	0.0276 (9)	−0.0033 (7)	−0.0025 (7)	−0.0010 (7)
N4	0.0277 (9)	0.0292 (10)	0.0262 (9)	−0.0026 (7)	−0.0035 (7)	0.0005 (7)
C1	0.0291 (11)	0.0284 (11)	0.0298 (11)	−0.0026 (8)	0.0014 (8)	−0.0049 (8)
C2	0.0345 (11)	0.0226 (11)	0.0330 (11)	−0.0016 (8)	−0.0031 (9)	−0.0048 (8)
C3	0.0324 (11)	0.0233 (11)	0.0298 (11)	−0.0056 (8)	−0.0043 (8)	−0.0011 (8)
C4	0.0256 (10)	0.0268 (11)	0.0268 (10)	−0.0040 (8)	−0.0065 (8)	−0.0017 (8)
C5	0.0279 (10)	0.0253 (11)	0.0267 (10)	−0.0035 (8)	−0.0067 (8)	0.0005 (8)
C6	0.0268 (10)	0.0307 (11)	0.0251 (10)	−0.0040 (8)	−0.0005 (8)	−0.0040 (8)
C7	0.0261 (10)	0.0264 (11)	0.0290 (11)	−0.0014 (8)	−0.0049 (8)	−0.0034 (8)
C8	0.0286 (11)	0.0291 (11)	0.0309 (11)	−0.0008 (8)	−0.0024 (8)	−0.0059 (8)
C9	0.0321 (11)	0.0235 (11)	0.0358 (11)	−0.0001 (8)	−0.0045 (9)	−0.0033 (8)
C10	0.0321 (11)	0.0215 (11)	0.0337 (11)	−0.0022 (8)	−0.0067 (9)	−0.0002 (8)
C11	0.0277 (10)	0.0236 (10)	0.0274 (10)	−0.0047 (8)	−0.0067 (8)	−0.0014 (8)
C12	0.0254 (10)	0.0246 (11)	0.0269 (10)	−0.0032 (8)	−0.0049 (8)	−0.0032 (8)
C13	0.0258 (10)	0.0268 (11)	0.0271 (10)	−0.0022 (8)	−0.0054 (8)	−0.0001 (8)
C14	0.0363 (12)	0.0315 (12)	0.0280 (11)	−0.0025 (9)	0.0030 (9)	−0.0026 (9)
C15	0.0403 (12)	0.0244 (11)	0.0334 (12)	−0.0009 (9)	0.0024 (9)	−0.0040 (8)
C16	0.0306 (11)	0.0268 (11)	0.0300 (11)	−0.0031 (8)	−0.0046 (8)	0.0013 (8)
C17	0.0274 (10)	0.0286 (11)	0.0267 (10)	−0.0024 (8)	−0.0023 (8)	−0.0029 (8)
C18	0.0281 (10)	0.0266 (11)	0.0276 (10)	0.0007 (8)	−0.0053 (8)	−0.0025 (8)

O1—C16	1.347 (2)	C6—C7	1.430 (3)
O1—H4	0.95 (3)	C6—H6	0.9500
O2—H20	0.84 (3)	C7—C11	1.404 (3)
O2—H21	0.85 (3)	C7—C8	1.408 (3)
N1—C1	1.327 (3)	C8—C9	1.376 (3)
N1—C12	1.355 (3)	C8—H8	0.9500
N2—C10	1.326 (3)	C9—C10	1.391 (3)
N2—C11	1.358 (3)	C9—H9	0.9500
N2—H19	0.87 (3)	C10—H10	0.9500
N3—N4	1.259 (2)	C11—C12	1.432 (3)
N3—C5	1.419 (3)	C13—C18	1.388 (3)
N4—C13	1.411 (3)	C13—C14	1.402 (3)
C1—C2	1.398 (3)	C14—C15	1.372 (3)
C1—H1	0.9500	C14—H14	0.9500
C2—C3	1.368 (3)	C15—C16	1.396 (3)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.409 (3)	C16—C17	1.395 (3)
C3—H3	0.9500	C17—C18	1.384 (3)
C4—C12	1.405 (3)	C17—H17	0.9500
C4—C5	1.444 (3)	C18—H18	0.9500
C5—C6	1.362 (3)
C16—O1—H4	112.0 (17)	C7—C8—H8	119.8
H20—O2—H21	103 (3)	C8—C9—C10	119.17 (19)
C1—N1—C12	116.57 (17)	C8—C9—H9	120.4
C10—N2—C11	123.09 (19)	C10—C9—H9	120.4
C10—N2—H19	120.1 (18)	N2—C10—C9	120.14 (19)
C11—N2—H19	116.8 (18)	N2—C10—H10	119.9
N4—N3—C5	115.16 (16)	C9—C10—H10	119.9
N3—N4—C13	113.91 (16)	N2—C11—C7	119.06 (18)
N1—C1—C2	123.65 (19)	N2—C11—C12	119.30 (18)
N1—C1—H1	118.2	C7—C11—C12	121.64 (18)
C2—C1—H1	118.2	N1—C12—C4	124.37 (18)
C3—C2—C1	119.52 (18)	N1—C12—C11	117.06 (17)
C3—C2—H2	120.2	C4—C12—C11	118.57 (18)
C1—C2—H2	120.2	C18—C13—C14	118.72 (19)
C2—C3—C4	119.12 (18)	C18—C13—N4	117.59 (18)
C2—C3—H3	120.4	C14—C13—N4	123.69 (18)
C4—C3—H3	120.4	C15—C14—C13	120.14 (19)
C12—C4—C3	116.77 (18)	C15—C14—H14	119.9
C12—C4—C5	119.30 (17)	C13—C14—H14	119.9
C3—C4—C5	123.92 (18)	C14—C15—C16	120.64 (19)
C6—C5—N3	124.55 (18)	C14—C15—H15	119.7
C6—C5—C4	121.23 (18)	C16—C15—H15	119.7
N3—C5—C4	114.16 (17)	O1—C16—C17	123.39 (19)
C5—C6—C7	120.71 (19)	O1—C16—C15	116.79 (18)
C5—C6—H6	119.6	C17—C16—C15	119.82 (19)
C7—C6—H6	119.6	C18—C17—C16	118.89 (19)
C11—C7—C8	118.16 (19)	C18—C17—H17	120.6
C11—C7—C6	118.55 (18)	C16—C17—H17	120.6
C8—C7—C6	123.28 (19)	C17—C18—C13	121.70 (18)
C9—C8—C7	120.38 (19)	C17—C18—H18	119.2
C9—C8—H8	119.8	C13—C18—H18	119.2
C5—N3—N4—C13	−178.33 (16)	C8—C7—C11—C12	179.75 (18)
C12—N1—C1—C2	0.2 (3)	C6—C7—C11—C12	0.2 (3)
N1—C1—C2—C3	−0.2 (3)	C1—N1—C12—C4	0.2 (3)
C1—C2—C3—C4	−0.2 (3)	C1—N1—C12—C11	179.76 (18)
C2—C3—C4—C12	0.6 (3)	C3—C4—C12—N1	−0.6 (3)
C2—C3—C4—C5	179.22 (19)	C5—C4—C12—N1	−179.33 (18)
N4—N3—C5—C6	13.2 (3)	C3—C4—C12—C11	179.85 (18)
N4—N3—C5—C4	−169.79 (17)	C5—C4—C12—C11	1.1 (3)
C12—C4—C5—C6	−0.7 (3)	N2—C11—C12—N1	−0.5 (3)
C3—C4—C5—C6	−179.33 (19)	C7—C11—C12—N1	179.51 (18)
C12—C4—C5—N3	−177.80 (17)	N2—C11—C12—C4	179.09 (17)
C3—C4—C5—N3	3.6 (3)	C7—C11—C12—C4	−0.9 (3)
N3—C5—C6—C7	176.79 (18)	N3—N4—C13—C18	−178.43 (17)
C4—C5—C6—C7	0.0 (3)	N3—N4—C13—C14	1.1 (3)
C5—C6—C7—C11	0.2 (3)	C18—C13—C14—C15	1.5 (3)
C5—C6—C7—C8	−179.3 (2)	N4—C13—C14—C15	−178.00 (19)
C11—C7—C8—C9	−0.3 (3)	C13—C14—C15—C16	1.2 (3)
C6—C7—C8—C9	179.22 (19)	C14—C15—C16—O1	177.6 (2)
C7—C8—C9—C10	0.7 (3)	C14—C15—C16—C17	−3.1 (3)
C11—N2—C10—C9	0.0 (3)	O1—C16—C17—C18	−178.53 (18)
C8—C9—C10—N2	−0.5 (3)	C15—C16—C17—C18	2.3 (3)
C10—N2—C11—C7	0.4 (3)	C16—C17—C18—C13	0.5 (3)
C10—N2—C11—C12	−179.60 (18)	C14—C13—C18—C17	−2.4 (3)
C8—C7—C11—N2	−0.3 (3)	N4—C13—C18—C17	177.18 (17)
C6—C7—C11—N2	−179.78 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H4···O2i	0.95 (3)	1.65 (3)	2.586 (2)	166 (3)
N2—H19···Cl1	0.87 (3)	2.35 (3)	3.1077 (19)	145 (2)
O2—H20···Cl1	0.84 (3)	2.25 (3)	3.0959 (16)	180 (3)
O2—H21···Cl1ii	0.85 (3)	2.30 (3)	3.1467 (17)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H4⋯O2i	0.95 (3)	1.65 (3)	2.586 (2)	166 (3)
N2—H19⋯Cl1	0.87 (3)	2.35 (3)	3.1077 (19)	145 (2)
O2—H20⋯Cl1	0.84 (3)	2.25 (3)	3.0959 (16)	180 (3)
O2—H21⋯Cl1ii	0.85 (3)	2.30 (3)	3.1467 (17)	170 (2)

Symmetry codes: (i) ; (ii) .