Aqua-dinitrato(quioxalino[2,3-f][1,10]phenanthroline)nickel(II) monohydrate.

In the crystal of the title compound, [Ni(NO(3))(2)(C(18)H(10)N(4))(H(2)O)]·H(2)O, the Ni(II) ion is coordinated in a distorted octahedral geometry by two N atoms of the 1,10-phenanthroline moiety of the ligand, three O atoms from two nitrate anions and an O atom from one water mol-ecule. O-H⋯O hydrogen bonds between the coordinated and the solvent water molecules and between these water molecules and the nitrate O atoms help to establish the crystal packing.

Related literature

For transition metal complexes and their potential applications as functional materials and enzymes, see: Noro et al. (2000 ▶); Yaghi et al. (1998 ▶). For quinoxaline derivates and 1,10-phenanthroline as electron-transporting materials, see: Ambroise & Maiya (2000 ▶); Lo & Hui (2005 ▶); Thomas et al. (2005 ▶).

Experimental

Crystal data

[Ni(NO3)2(C18H10N4)(H2O)]·H2O

M = 501.04

Monoclinic,

a = 7.300 (3) Å

b = 27.872 (12) Å

c = 9.950 (4) Å

β = 109.005 (6)°

V = 1914.1 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.08 mm−1

T = 293 K

0.24 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.792, T max = 0.805

12703 measured reflections

3338 independent reflections

2255 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 0.99

3338 reflections

314 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.02 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011441/at2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011441/at2754Isup2.hkl

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

[Ni(NO3)2(C18H10N4)(H2O)]·H2O	F(000) = 1024
Mr = 501.04	Dx = 1.739 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3338 reflections
a = 7.300 (3) Å	θ = 1.5–25.0°
b = 27.872 (12) Å	µ = 1.08 mm−1
c = 9.950 (4) Å	T = 293 K
β = 109.005 (6)°	Prism, green
V = 1914.1 (14) Å3	0.24 × 0.21 × 0.19 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3338 independent reflections
Radiation source: fine-focus sealed tube	2255 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.792, Tmax = 0.805	k = −29→33
12703 measured reflections	l = −11→11

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) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0654P)2] where P = (Fo2 + 2Fc2)/3
3338 reflections	(Δ/σ)max < 0.001
314 parameters	Δρmax = 1.02 e Å−3
4 restraints	Δρmin = −0.35 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
O1W	0.4569 (6)	0.23839 (11)	0.3617 (4)	0.0500 (8)
O2W	−0.2513 (6)	0.25558 (15)	0.2685 (5)	0.0748 (11)
H1WA	0.355 (5)	0.246 (2)	0.298 (5)	0.11 (2)*
H2WA	−0.140 (4)	0.246 (2)	0.313 (6)	0.10 (2)*
H2WB	−0.229 (10)	0.271 (2)	0.205 (5)	0.12 (3)*
H1WB	0.559 (5)	0.2429 (19)	0.343 (6)	0.08 (2)*
C1	0.2027 (6)	−0.07484 (15)	0.0816 (4)	0.0381 (10)
C2	0.1687 (7)	−0.12547 (15)	0.0792 (5)	0.0491 (12)
H2	0.1650	−0.1412	0.1607	0.059*
C3	0.1418 (7)	−0.15036 (16)	−0.0432 (5)	0.0509 (12)
H3	0.1195	−0.1832	−0.0441	0.061*
C4	0.1467 (6)	−0.12769 (16)	−0.1693 (5)	0.0473 (11)
H4	0.1275	−0.1455	−0.2518	0.057*
C5	0.1798 (6)	−0.07968 (15)	−0.1691 (4)	0.0437 (11)
H5	0.1829	−0.0648	−0.2521	0.052*
C6	0.2095 (6)	−0.05199 (15)	−0.0451 (4)	0.0389 (10)
C7	0.2656 (6)	0.02039 (14)	0.0708 (4)	0.0367 (10)
C8	0.3059 (6)	0.07219 (14)	0.0721 (4)	0.0361 (10)
C9	0.3115 (6)	0.09755 (15)	−0.0475 (4)	0.0435 (11)
H9	0.2845	0.0820	−0.1345	0.052*
C10	0.3567 (7)	0.14525 (15)	−0.0365 (4)	0.0448 (11)
H10	0.3597	0.1624	−0.1159	0.054*
C11	0.3984 (6)	0.16799 (15)	0.0953 (4)	0.0418 (11)
H11	0.4364	0.2000	0.1031	0.050*
C12	0.3390 (5)	0.09756 (13)	0.1985 (4)	0.0331 (9)
C13	0.3222 (5)	0.07486 (14)	0.3249 (4)	0.0325 (9)
C14	0.3228 (6)	0.08498 (15)	0.5558 (4)	0.0434 (11)
H14	0.3396	0.1046	0.6345	0.052*
C15	0.2730 (7)	0.03711 (15)	0.5646 (4)	0.0478 (12)
H15	0.2554	0.0254	0.6470	0.057*
C16	0.2501 (6)	0.00718 (15)	0.4488 (4)	0.0435 (11)
H16	0.2178	−0.0250	0.4524	0.052*
C17	0.2766 (6)	0.02637 (14)	0.3261 (4)	0.0343 (10)
C18	0.2550 (6)	−0.00271 (14)	0.1970 (4)	0.0360 (10)
N1	0.2418 (5)	−0.00420 (12)	−0.0496 (3)	0.0386 (8)
N2	0.2264 (5)	−0.04985 (12)	0.2022 (3)	0.0393 (8)
N3	0.3856 (5)	0.14541 (11)	0.2110 (3)	0.0364 (8)
N4	0.3473 (5)	0.10402 (12)	0.4398 (3)	0.0371 (8)
N5	0.8338 (6)	0.13711 (13)	0.5559 (4)	0.0462 (9)
N6	0.1912 (5)	0.21527 (13)	0.5388 (4)	0.0448 (9)
O1	0.7783 (5)	0.10649 (12)	0.4602 (3)	0.0641 (10)
O2	0.9965 (4)	0.13624 (12)	0.6460 (4)	0.0659 (10)
O3	0.7158 (4)	0.17099 (11)	0.5592 (3)	0.0546 (9)
O4	0.0965 (5)	0.20873 (11)	0.4119 (3)	0.0591 (9)
O5	0.3600 (4)	0.19605 (10)	0.5873 (3)	0.0455 (8)
O6	0.1315 (5)	0.23972 (12)	0.6206 (4)	0.0602 (9)
Ni1	0.42395 (7)	0.170749 (17)	0.40994 (5)	0.0345 (2)

	U11	U22	U33	U12	U13	U23
O1W	0.065 (3)	0.0339 (19)	0.049 (2)	−0.0001 (18)	0.016 (2)	−0.0016 (15)
O2W	0.057 (3)	0.073 (3)	0.090 (3)	0.008 (2)	0.018 (2)	0.035 (2)
C1	0.041 (2)	0.033 (2)	0.043 (2)	−0.0042 (19)	0.0175 (19)	−0.007 (2)
C2	0.064 (3)	0.034 (3)	0.054 (3)	−0.003 (2)	0.026 (2)	0.001 (2)
C3	0.062 (3)	0.029 (2)	0.067 (3)	−0.008 (2)	0.029 (3)	−0.011 (2)
C4	0.055 (3)	0.041 (3)	0.048 (3)	−0.006 (2)	0.020 (2)	−0.011 (2)
C5	0.052 (3)	0.037 (3)	0.042 (2)	−0.008 (2)	0.015 (2)	−0.005 (2)
C6	0.038 (2)	0.034 (3)	0.044 (2)	−0.0006 (19)	0.0121 (19)	−0.007 (2)
C7	0.041 (2)	0.033 (2)	0.035 (2)	0.0029 (18)	0.0112 (18)	−0.0014 (18)
C8	0.042 (2)	0.031 (2)	0.035 (2)	0.0029 (19)	0.0113 (18)	0.0000 (18)
C9	0.058 (3)	0.037 (3)	0.033 (2)	−0.002 (2)	0.012 (2)	−0.0036 (19)
C10	0.069 (3)	0.029 (2)	0.042 (2)	0.001 (2)	0.025 (2)	0.005 (2)
C11	0.053 (3)	0.029 (2)	0.045 (3)	−0.001 (2)	0.018 (2)	0.002 (2)
C12	0.035 (2)	0.026 (2)	0.037 (2)	0.0036 (18)	0.0107 (18)	0.0009 (18)
C13	0.034 (2)	0.029 (2)	0.034 (2)	0.0008 (18)	0.0113 (17)	−0.0007 (18)
C14	0.055 (3)	0.039 (3)	0.039 (2)	0.003 (2)	0.019 (2)	−0.005 (2)
C15	0.071 (3)	0.035 (3)	0.043 (2)	0.000 (2)	0.027 (2)	0.002 (2)
C16	0.062 (3)	0.030 (2)	0.045 (3)	−0.003 (2)	0.026 (2)	−0.003 (2)
C17	0.037 (2)	0.033 (2)	0.036 (2)	0.0023 (18)	0.0162 (18)	−0.0001 (18)
C18	0.040 (2)	0.030 (2)	0.038 (2)	0.0006 (18)	0.0131 (18)	−0.0015 (19)
N1	0.046 (2)	0.034 (2)	0.0349 (19)	−0.0001 (16)	0.0117 (16)	−0.0026 (16)
N2	0.052 (2)	0.029 (2)	0.0410 (19)	0.0008 (16)	0.0214 (17)	−0.0016 (16)
N3	0.041 (2)	0.0288 (19)	0.041 (2)	−0.0005 (15)	0.0146 (16)	−0.0008 (16)
N4	0.044 (2)	0.032 (2)	0.0355 (19)	0.0018 (16)	0.0143 (16)	−0.0030 (16)
N5	0.057 (3)	0.039 (2)	0.048 (2)	0.001 (2)	0.025 (2)	0.0066 (19)
N6	0.048 (2)	0.035 (2)	0.052 (2)	−0.0032 (18)	0.018 (2)	−0.0110 (18)
O1	0.084 (3)	0.055 (2)	0.056 (2)	0.0090 (19)	0.0272 (19)	−0.0098 (18)
O2	0.043 (2)	0.080 (3)	0.069 (2)	0.0116 (18)	0.0104 (18)	0.0144 (19)
O3	0.0478 (19)	0.0411 (19)	0.068 (2)	0.0069 (16)	0.0097 (16)	−0.0122 (16)
O4	0.057 (2)	0.064 (2)	0.0475 (19)	0.0018 (17)	0.0046 (16)	−0.0121 (16)
O5	0.0441 (18)	0.0402 (18)	0.0500 (18)	0.0038 (14)	0.0123 (14)	−0.0040 (14)
O6	0.062 (2)	0.055 (2)	0.071 (2)	0.0023 (17)	0.0325 (18)	−0.0205 (18)
Ni1	0.0469 (4)	0.0241 (3)	0.0321 (3)	−0.0013 (2)	0.0122 (2)	−0.0036 (2)

O1W—Ni1	1.979 (3)	C11—H11	0.9300
O1W—H1WA	0.83 (2)	C12—N3	1.372 (5)
O1W—H1WB	0.83 (2)	C12—C13	1.448 (5)
O2W—H2WA	0.83 (2)	C13—N4	1.366 (5)
O2W—H2WB	0.83 (2)	C13—C17	1.393 (5)
C1—N2	1.349 (5)	C14—N4	1.334 (5)
C1—C6	1.427 (6)	C14—C15	1.393 (6)
C1—C2	1.432 (6)	C14—H14	0.9300
C2—C3	1.359 (6)	C15—C16	1.388 (6)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.416 (6)	C16—C17	1.402 (5)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.360 (6)	C17—C18	1.484 (5)
C4—H4	0.9300	C18—N2	1.334 (5)
C5—C6	1.411 (5)	N3—Ni1	2.033 (3)
C5—H5	0.9300	N4—Ni1	1.992 (3)
C6—N1	1.356 (5)	N5—O2	1.233 (4)
C7—N1	1.341 (5)	N5—O1	1.244 (4)
C7—C18	1.436 (5)	N5—O3	1.286 (4)
C7—C8	1.472 (5)	N6—O4	1.240 (4)
C8—C12	1.393 (5)	N6—O4	1.240 (4)
C8—C9	1.396 (5)	N6—O6	1.244 (4)
C9—C10	1.366 (6)	N6—O5	1.285 (4)
C9—H9	0.9300	O3—Ni1	2.164 (3)
C10—C11	1.399 (6)	O4—O4	0.000 (6)
C10—H10	0.9300	O5—Ni1	2.090 (3)
C11—N3	1.342 (5)
Ni1—O1W—H1WA	106 (4)	N4—C14—H14	118.4
Ni1—O1W—H1WB	113 (4)	C15—C14—H14	118.4
H1WA—O1W—H1WB	116 (6)	C16—C15—C14	119.1 (4)
H2WA—O2W—H2WB	100 (6)	C16—C15—H15	120.4
N2—C1—C6	121.6 (4)	C14—C15—H15	120.4
N2—C1—C2	119.7 (4)	C15—C16—C17	118.7 (4)
C6—C1—C2	118.7 (4)	C15—C16—H16	120.7
C3—C2—C1	119.5 (4)	C17—C16—H16	120.7
C3—C2—H2	120.3	C13—C17—C16	118.6 (4)
C1—C2—H2	120.3	C13—C17—C18	118.7 (3)
C2—C3—C4	121.9 (4)	C16—C17—C18	122.6 (4)
C2—C3—H3	119.1	N2—C18—C7	121.9 (4)
C4—C3—H3	119.1	N2—C18—C17	118.6 (3)
C5—C4—C3	119.6 (4)	C7—C18—C17	119.5 (4)
C5—C4—H4	120.2	C7—N1—C6	116.5 (3)
C3—C4—H4	120.2	C18—N2—C1	116.8 (3)
C4—C5—C6	121.1 (4)	C11—N3—C12	117.5 (3)
C4—C5—H5	119.5	C11—N3—Ni1	130.3 (3)
C6—C5—H5	119.5	C12—N3—Ni1	112.2 (2)
N1—C6—C5	119.2 (4)	C14—N4—C13	117.9 (3)
N1—C6—C1	121.6 (4)	C14—N4—Ni1	128.6 (3)
C5—C6—C1	119.3 (4)	C13—N4—Ni1	113.5 (3)
N1—C7—C18	121.6 (4)	O2—N5—O1	122.7 (4)
N1—C7—C8	118.5 (4)	O2—N5—O3	119.3 (4)
C18—C7—C8	119.9 (3)	O1—N5—O3	118.0 (4)
C12—C8—C9	117.9 (4)	O4—N6—O4	0.0 (4)
C12—C8—C7	118.8 (4)	O4—N6—O6	123.3 (4)
C9—C8—C7	123.4 (4)	O4—N6—O6	123.3 (4)
C10—C9—C8	119.9 (4)	O4—N6—O5	118.0 (4)
C10—C9—H9	120.1	O4—N6—O5	118.0 (4)
C8—C9—H9	120.1	O6—N6—O5	118.7 (4)
C9—C10—C11	119.3 (4)	N5—O3—Ni1	119.9 (3)
C9—C10—H10	120.4	O4—O4—N6	0(10)
C11—C10—H10	120.4	N6—O5—Ni1	105.9 (2)
N3—C11—C10	122.5 (4)	O1W—Ni1—N4	170.98 (15)
N3—C11—H11	118.7	O1W—Ni1—N3	94.82 (14)
C10—C11—H11	118.7	N4—Ni1—N3	82.22 (13)
N3—C12—C8	122.7 (4)	O1W—Ni1—O5	87.80 (13)
N3—C12—C13	115.7 (3)	N4—Ni1—O5	92.19 (12)
C8—C12—C13	121.5 (4)	N3—Ni1—O5	160.31 (12)
N4—C13—C17	122.5 (4)	O1W—Ni1—O3	89.62 (14)
N4—C13—C12	116.2 (3)	N4—Ni1—O3	99.32 (12)
C17—C13—C12	121.3 (3)	N3—Ni1—O3	117.52 (13)
N4—C14—C15	123.1 (4)	O5—Ni1—O3	81.96 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O6i	0.83 (2)	2.02 (2)	2.839 (5)	170 (6)
O1W—H1WB···O2Wii	0.83 (2)	1.81 (2)	2.630 (6)	169 (6)
O2W—H2WB···O3iii	0.83 (2)	2.11 (4)	2.873 (5)	153 (7)
O2W—H2WA···O4	0.83 (2)	1.98 (2)	2.798 (5)	167 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O6i	0.83 (2)	2.02 (2)	2.839 (5)	170 (6)
O1W—H1WB⋯O2Wii	0.83 (2)	1.81 (2)	2.630 (6)	169 (6)
O2W—H2WB⋯O3iii	0.83 (2)	2.11 (4)	2.873 (5)	153 (7)
O2W—H2WA⋯O4	0.83 (2)	1.98 (2)	2.798 (5)	167 (6)

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