Triaqua-(2,2'-bipyridine N,N'-dioxide-κO,O')(5-nitro-benzene-1,3-dicarboxyl-ato-κO)zinc(II).

In the title compound, [Zn(C(8)H(3)NO(6))(C(10)H(8)N(2)O(2))(H(2)O)(3)], the Zn(II) ion is coordinated in a distorted octa-hedral geometry by three water mol-ecules, one O atom from a 5-nitro-benzene-1,3-dicarboxyl-ate ligand and two O atoms from a chelating 2,2'-bipyridine N,N'-dioxide ligand. An extensive network of O-H⋯O hydrogen bonds is formed between the water mol-ecules and the carboxyl-ate groups. C-H⋯O inter-actions are also present.

Related literature

For metal complexes containing the 2,2′-bipyridine-N,N′-dioxide ligand, see: Hill et al. (2004 ▶); Long et al. (2001 ▶); Ma et al. (2003 ▶).

Experimental

Crystal data

[Zn(C8H3NO6)(C10H8N2O2)(H2O)3]

M = 516.72

Triclinic,

a = 8.3040 (14) Å

b = 10.7036 (18) Å

c = 11.6546 (19) Å

α = 87.217 (3)°

β = 88.436 (3)°

γ = 87.006 (3)°

V = 1032.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.26 mm−1

T = 294 K

0.20 × 0.19 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.778, T max = 0.828

6281 measured reflections

3604 independent reflections

2737 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.143

S = 1.05

3604 reflections

316 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.52 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015451/gk2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015451/gk2207Isup2.hkl

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

[Zn(C8H3NO6)(C10H8N2O2)(H2O)3]	Z = 2
Mr = 516.72	F(000) = 528
Triclinic, P1	Dx = 1.661 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3040 (14) Å	Cell parameters from 1831 reflections
b = 10.7036 (18) Å	θ = 2.5–25.8°
c = 11.6546 (19) Å	µ = 1.26 mm−1
α = 87.217 (3)°	T = 294 K
β = 88.436 (3)°	Plate, colourless
γ = 87.006 (3)°	0.20 × 0.19 × 0.15 mm
V = 1032.9 (3) Å3

Bruker SMART CCD area-detector diffractometer	3604 independent reflections
Radiation source: fine-focus sealed tube	2737 reflections with I > 2σ(I)
graphite	Rint = 0.075
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.778, Tmax = 0.828	l = −13→12
6281 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0678P)2] where P = (Fo2 + 2Fc2)/3
3604 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.62 e Å−3
15 restraints	Δρmin = −0.52 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
C1	0.1974 (7)	0.7637 (5)	0.4162 (4)	0.0393 (13)
H1	0.2819	0.7530	0.3629	0.047*
C2	0.0764 (7)	0.8456 (5)	0.3923 (5)	0.0501 (15)
H2	0.0790	0.8941	0.3239	0.060*
C3	−0.0552 (7)	0.8599 (5)	0.4689 (5)	0.0422 (14)
H3	−0.1426	0.9146	0.4510	0.051*
C4	−0.0514 (7)	0.7907 (5)	0.5715 (5)	0.0419 (13)
H4	−0.1365	0.7988	0.6245	0.050*
C5	0.0808 (6)	0.7082 (4)	0.5958 (4)	0.0291 (11)
C6	0.0829 (6)	0.6224 (4)	0.6979 (4)	0.0316 (11)
C7	−0.0296 (7)	0.5359 (5)	0.7202 (5)	0.0446 (14)
H7	−0.1152	0.5322	0.6710	0.054*
C8	−0.0185 (7)	0.4531 (5)	0.8157 (5)	0.0467 (15)
H8	−0.0946	0.3931	0.8298	0.056*
C9	0.1038 (7)	0.4616 (5)	0.8867 (5)	0.0437 (14)
H9	0.1116	0.4074	0.9514	0.052*
C10	0.2200 (6)	0.5500 (5)	0.8659 (4)	0.0383 (12)
H10	0.3051	0.5543	0.9155	0.046*
C11	0.6375 (6)	0.7121 (4)	0.8717 (4)	0.0319 (11)
C12	0.6641 (6)	0.8090 (4)	0.9588 (4)	0.0294 (11)
C13	0.6310 (6)	0.7849 (4)	1.0732 (4)	0.0315 (12)
H13	0.5928	0.7074	1.0966	0.038*
C14	0.6522 (6)	0.8719 (4)	1.1562 (4)	0.0279 (11)
C15	0.6128 (6)	0.8387 (4)	1.2805 (4)	0.0313 (12)
C16	0.7084 (6)	0.9882 (4)	1.1206 (4)	0.0308 (11)
H16	0.7229	1.0490	1.1732	0.037*
C17	0.7419 (6)	1.0105 (4)	1.0055 (4)	0.0305 (11)
C18	0.7202 (6)	0.9267 (5)	0.9228 (4)	0.0345 (12)
H18	0.7417	0.9469	0.8456	0.041*
N1	0.1998 (5)	0.6958 (4)	0.5163 (3)	0.0334 (10)
N2	0.2069 (5)	0.6291 (4)	0.7726 (3)	0.0337 (10)
N3	0.8039 (6)	1.1326 (4)	0.9671 (4)	0.0534 (14)
O1	0.3113 (4)	0.7178 (3)	0.7539 (3)	0.0333 (8)
O2	0.3271 (4)	0.6146 (3)	0.5377 (3)	0.0321 (8)
O3	0.6489 (4)	0.7466 (3)	0.7662 (3)	0.0352 (8)
O4	0.6108 (5)	0.6041 (3)	0.9116 (3)	0.0420 (9)
O5	0.5983 (5)	0.7257 (3)	1.3088 (3)	0.0444 (10)
O6	0.5973 (5)	0.9246 (3)	1.3487 (3)	0.0473 (10)
O7	0.8838 (7)	1.1868 (4)	1.0367 (4)	0.0822 (16)
O8	0.7846 (7)	1.1702 (4)	0.8683 (4)	0.0804 (16)
O9	0.5579 (5)	0.4929 (3)	0.7204 (3)	0.0339 (8)
H9A	0.546 (7)	0.418 (2)	0.732 (4)	0.051*
H9B	0.562 (7)	0.518 (4)	0.786 (2)	0.051*
O10	0.4917 (6)	0.8518 (3)	0.5648 (3)	0.0561 (12)
H10A	0.544 (7)	0.872 (6)	0.509 (4)	0.084*
H10B	0.421 (6)	0.904 (5)	0.583 (5)	0.084*
O11	0.6736 (4)	0.6260 (3)	0.5182 (3)	0.0326 (8)
H11A	0.640 (6)	0.556 (2)	0.514 (4)	0.049*
H11B	0.644 (6)	0.664 (4)	0.458 (3)	0.049*
Zn1	0.50994 (7)	0.67555 (5)	0.64551 (4)	0.0280 (2)

	U11	U22	U33	U12	U13	U23
C1	0.045 (3)	0.047 (3)	0.025 (3)	0.002 (3)	0.001 (2)	0.001 (2)
C2	0.064 (4)	0.049 (4)	0.036 (3)	−0.006 (3)	−0.001 (3)	0.014 (3)
C3	0.039 (3)	0.034 (3)	0.053 (4)	−0.002 (2)	−0.009 (3)	0.005 (3)
C4	0.049 (3)	0.033 (3)	0.045 (3)	−0.016 (3)	0.003 (3)	−0.002 (3)
C5	0.025 (3)	0.031 (3)	0.032 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
C6	0.032 (3)	0.031 (3)	0.031 (3)	−0.005 (2)	0.005 (2)	0.005 (2)
C7	0.055 (4)	0.039 (3)	0.041 (3)	−0.012 (3)	0.003 (3)	0.004 (3)
C8	0.051 (4)	0.037 (3)	0.052 (4)	−0.015 (3)	0.011 (3)	0.007 (3)
C9	0.059 (4)	0.035 (3)	0.035 (3)	−0.002 (3)	0.009 (3)	0.011 (2)
C10	0.041 (3)	0.042 (3)	0.032 (3)	0.003 (2)	0.003 (2)	−0.002 (2)
C11	0.039 (3)	0.032 (3)	0.026 (3)	−0.004 (2)	0.001 (2)	−0.007 (2)
C12	0.040 (3)	0.025 (3)	0.022 (3)	−0.003 (2)	0.001 (2)	0.000 (2)
C13	0.053 (3)	0.017 (2)	0.024 (3)	−0.004 (2)	0.005 (2)	−0.004 (2)
C14	0.036 (3)	0.027 (3)	0.020 (2)	−0.002 (2)	0.003 (2)	0.000 (2)
C15	0.046 (3)	0.021 (3)	0.027 (3)	−0.006 (2)	0.005 (2)	−0.007 (2)
C16	0.036 (3)	0.027 (3)	0.029 (3)	−0.005 (2)	0.004 (2)	−0.004 (2)
C17	0.037 (3)	0.021 (2)	0.034 (3)	−0.010 (2)	0.009 (2)	−0.002 (2)
C18	0.045 (3)	0.038 (3)	0.021 (3)	−0.011 (2)	0.008 (2)	0.005 (2)
N1	0.049 (3)	0.028 (2)	0.024 (2)	−0.0079 (19)	−0.001 (2)	−0.0047 (18)
N2	0.048 (3)	0.028 (2)	0.025 (2)	−0.0071 (19)	0.012 (2)	0.0035 (18)
N3	0.083 (4)	0.034 (3)	0.043 (3)	−0.021 (3)	0.028 (3)	−0.007 (2)
O1	0.0317 (18)	0.035 (2)	0.0343 (19)	−0.0105 (15)	0.0064 (15)	−0.0039 (15)
O2	0.0346 (19)	0.0302 (19)	0.0315 (19)	0.0060 (15)	−0.0029 (15)	−0.0078 (15)
O3	0.056 (2)	0.035 (2)	0.0162 (17)	−0.0189 (17)	0.0065 (16)	−0.0040 (14)
O4	0.075 (3)	0.027 (2)	0.0250 (19)	−0.0127 (18)	−0.0032 (18)	−0.0032 (15)
O5	0.089 (3)	0.0219 (19)	0.0234 (19)	−0.0153 (18)	0.0033 (19)	0.0003 (14)
O6	0.089 (3)	0.028 (2)	0.0233 (19)	−0.0018 (19)	0.0155 (19)	−0.0030 (16)
O7	0.141 (5)	0.055 (3)	0.056 (3)	−0.055 (3)	0.033 (3)	−0.023 (2)
O8	0.136 (5)	0.056 (3)	0.051 (3)	−0.041 (3)	0.012 (3)	0.019 (2)
O9	0.054 (2)	0.0217 (18)	0.0266 (19)	−0.0063 (17)	−0.0021 (17)	−0.0016 (15)
O10	0.118 (4)	0.021 (2)	0.028 (2)	−0.003 (2)	0.026 (2)	−0.0001 (16)
O11	0.048 (2)	0.0273 (19)	0.0229 (19)	−0.0100 (17)	0.0039 (16)	0.0005 (15)
Zn1	0.0418 (4)	0.0228 (3)	0.0197 (3)	−0.0056 (2)	0.0028 (2)	−0.0024 (2)

C1—C2	1.325 (7)	C13—H13	0.9300
C1—N1	1.344 (6)	C14—C16	1.393 (6)
C1—H1	0.9300	C14—C15	1.507 (6)
C2—C3	1.399 (8)	C15—O6	1.243 (5)
C2—H2	0.9300	C15—O5	1.249 (5)
C3—C4	1.375 (7)	C16—C17	1.374 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.398 (7)	C17—C18	1.370 (6)
C4—H4	0.9300	C17—N3	1.475 (6)
C5—N1	1.342 (6)	C18—H18	0.9300
C5—C6	1.468 (6)	N1—O2	1.353 (5)
C6—C7	1.361 (7)	N2—O1	1.325 (5)
C6—N2	1.374 (6)	N3—O8	1.214 (6)
C7—C8	1.390 (7)	N3—O7	1.244 (6)
C7—H7	0.9300	O1—Zn1	2.094 (3)
C8—C9	1.338 (7)	O2—Zn1	2.144 (3)
C8—H8	0.9300	O3—Zn1	2.043 (3)
C9—C10	1.394 (7)	O9—Zn1	2.125 (3)
C9—H9	0.9300	O9—H9A	0.816 (19)
C10—N2	1.349 (6)	O9—H9B	0.821 (19)
C10—H10	0.9300	O10—Zn1	2.067 (3)
C11—O4	1.254 (5)	O10—H10A	0.80 (2)
C11—O3	1.268 (5)	O10—H10B	0.818 (19)
C11—C12	1.514 (6)	O11—Zn1	2.054 (4)
C12—C13	1.370 (6)	O11—H11A	0.814 (19)
C12—C18	1.407 (6)	O11—H11B	0.833 (19)
C13—C14	1.395 (6)
C2—C1—N1	120.9 (5)	C17—C16—C14	118.1 (4)
C2—C1—H1	119.5	C17—C16—H16	121.0
N1—C1—H1	119.5	C14—C16—H16	121.0
C1—C2—C3	120.7 (5)	C18—C17—C16	124.3 (4)
C1—C2—H2	119.7	C18—C17—N3	117.2 (4)
C3—C2—H2	119.7	C16—C17—N3	118.6 (4)
C4—C3—C2	118.0 (5)	C17—C18—C12	117.7 (4)
C4—C3—H3	121.0	C17—C18—H18	121.2
C2—C3—H3	121.0	C12—C18—H18	121.2
C3—C4—C5	119.9 (5)	C5—N1—C1	121.6 (5)
C3—C4—H4	120.1	C5—N1—O2	119.5 (4)
C5—C4—H4	120.1	C1—N1—O2	118.9 (4)
N1—C5—C4	118.8 (5)	O1—N2—C10	120.1 (4)
N1—C5—C6	118.7 (4)	O1—N2—C6	118.9 (4)
C4—C5—C6	122.0 (4)	C10—N2—C6	121.0 (4)
C7—C6—N2	119.1 (5)	O8—N3—O7	123.8 (5)
C7—C6—C5	123.2 (5)	O8—N3—C17	118.8 (5)
N2—C6—C5	117.8 (4)	O7—N3—C17	117.2 (5)
C6—C7—C8	121.0 (5)	N2—O1—Zn1	116.6 (3)
C6—C7—H7	119.5	N1—O2—Zn1	117.1 (2)
C8—C7—H7	119.5	C11—O3—Zn1	121.9 (3)
C9—C8—C7	118.6 (5)	Zn1—O9—H9A	157 (4)
C9—C8—H8	120.7	Zn1—O9—H9B	93 (3)
C7—C8—H8	120.7	H9A—O9—H9B	102 (4)
C8—C9—C10	121.4 (5)	Zn1—O10—H10A	124 (4)
C8—C9—H9	119.3	Zn1—O10—H10B	122 (4)
C10—C9—H9	119.3	H10A—O10—H10B	114 (5)
N2—C10—C9	119.0 (5)	Zn1—O11—H11A	94 (4)
N2—C10—H10	120.5	Zn1—O11—H11B	107 (4)
C9—C10—H10	120.5	H11A—O11—H11B	104 (4)
O4—C11—O3	126.4 (4)	O3—Zn1—O11	103.59 (13)
O4—C11—C12	116.2 (4)	O3—Zn1—O10	88.62 (16)
O3—C11—C12	117.4 (4)	O11—Zn1—O10	87.49 (15)
C13—C12—C18	118.8 (4)	O3—Zn1—O1	86.88 (13)
C13—C12—C11	120.9 (4)	O11—Zn1—O1	169.46 (12)
C18—C12—C11	120.3 (4)	O10—Zn1—O1	91.57 (15)
C12—C13—C14	122.7 (4)	O3—Zn1—O9	89.47 (13)
C12—C13—H13	118.6	O11—Zn1—O9	86.47 (13)
C14—C13—H13	118.6	O10—Zn1—O9	173.05 (17)
C16—C14—C13	118.4 (4)	O1—Zn1—O9	95.00 (13)
C16—C14—C15	121.9 (4)	O3—Zn1—O2	169.33 (13)
C13—C14—C15	119.7 (4)	O11—Zn1—O2	86.92 (12)
O6—C15—O5	124.0 (5)	O10—Zn1—O2	90.04 (16)
O6—C15—C14	118.4 (4)	O1—Zn1—O2	82.58 (12)
O5—C15—C14	117.6 (4)	O9—Zn1—O2	93.05 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O5i	0.82 (3)	2.08 (4)	2.773 (5)	143 (5)
O9—H9B···O4	0.83 (3)	1.83 (3)	2.635 (5)	164 (4)
O10—H10A···O6ii	0.81 (5)	1.96 (5)	2.735 (5)	161 (6)
O10—H10B···O6iii	0.82 (5)	2.03 (5)	2.702 (5)	139 (5)
O11—H11A···O2iv	0.82 (3)	1.95 (3)	2.687 (5)	149 (5)
O11—H11B···O5ii	0.83 (3)	1.87 (4)	2.692 (5)	169 (4)
C2—H2···O8v	0.93	2.59	3.229 (8)	126
C3—H3···O6vi	0.93	2.49	3.269 (7)	141
C4—H4···O3vii	0.93	2.46	3.358 (7)	162
C13—H13···O4i	0.93	2.47	2.780 (6)	100

Table 1

Selected bond lengths (Å)

O1—Zn1	2.094 (3)
O2—Zn1	2.144 (3)
O3—Zn1	2.043 (3)
O9—Zn1	2.125 (3)
O10—Zn1	2.067 (3)
O11—Zn1	2.054 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O5i	0.82 (3)	2.08 (4)	2.773 (5)	143 (5)
O9—H9B⋯O4	0.83 (3)	1.83 (3)	2.635 (5)	164 (4)
O10—H10A⋯O6ii	0.81 (5)	1.96 (5)	2.735 (5)	161 (6)
O10—H10B⋯O6iii	0.82 (5)	2.03 (5)	2.702 (5)	139 (5)
O11—H11A⋯O2iv	0.82 (3)	1.95 (3)	2.687 (5)	149 (5)
O11—H11B⋯O5ii	0.83 (3)	1.87 (4)	2.692 (5)	169 (4)
C2—H2⋯O8v	0.93	2.59	3.229 (8)	126
C3—H3⋯O6vi	0.93	2.49	3.269 (7)	141
C4—H4⋯O3vii	0.93	2.46	3.358 (7)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .