Diaqua-bis(2,2'-biimidazole)zinc(II) 4,4'-di-carboxybiphenyl-3,3'-di-carboxyl-ate.

In the title compound, [Zn(C(6)H(6)N(4))(2)(H(2)O)(2)](C(16)H(8)O(8)), the Zn(II) atom, located on an inversion centre, is coordinated by two aqua and two bidentate biimidizole ligands, resulting in a slightly distorted octa-hedral ZnO(2)N(4) geometry. The four N atoms from the two biimidizole ligands lie in the equatorial plane and the two aqua O atoms lie in the axial sites. The biphenyl-tetra-carboxyl-ate anion also lies on an inversion centre. The Zn(II) complex cation and the anion are held together by N-H⋯O hydrogen bonds, forming a zigzag chain along [21]. The chains are further connected by water mol-ecules via O-H⋯O hydrogen bonds.

Related literature

For general background, see: Hagrman et al. (1999 ▶); Jia et al. (2007 ▶); Kortz et al. (2003 ▶).

Experimental

Crystal data

[Zn(C6H6N4)2(H2O)2](C16H8O8)

M = 697.92

Triclinic,

a = 8.2133 (16) Å

b = 9.810 (2) Å

c = 10.498 (2) Å

α = 63.72 (3)°

β = 68.00 (3)°

γ = 83.85 (3)°

V = 701.4 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.95 mm−1

T = 293 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (; Bruker, 2001 ▶) T min = 0.894, T max = 0.928

5074 measured reflections

2674 independent reflections

2579 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.00

2674 reflections

218 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); 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 global, I. DOI: 10.1107/S1600536809008022/is2385sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008022/is2385Isup2.hkl

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

[Zn(C6H6N4)2(H2O)2](C16H8O8)	Z = 1
Mr = 697.92	F(000) = 358
Triclinic, P1	Dx = 1.652 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2133 (16) Å	Cell parameters from 2674 reflections
b = 9.810 (2) Å	θ = 3.4–26.0°
c = 10.498 (2) Å	µ = 0.95 mm−1
α = 63.72 (3)°	T = 293 K
β = 68.00 (3)°	Block, colorless
γ = 83.85 (3)°	0.12 × 0.10 × 0.08 mm
V = 701.4 (2) Å3

Bruker APEXII CCD diffractometer	2674 independent reflections
Radiation source: fine-focus sealed tube	2579 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
Tmin = 0.894, Tmax = 0.928	k = −12→12
5074 measured reflections	l = −12→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.052P)2 + 0.4235P] where P = (Fo2 + 2Fc2)/3
2674 reflections	(Δ/σ)max = 0.018
218 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.22 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
Zn1	0.5000	0.5000	0.0000	0.03706 (14)
C1	0.8917 (3)	−0.0165 (3)	0.6897 (3)	0.0359 (5)
C2	0.7565 (3)	0.0726 (2)	0.6220 (2)	0.0299 (4)
C3	0.6742 (3)	−0.0082 (2)	0.5790 (2)	0.0317 (4)
H3	0.7113	−0.1040	0.5887	0.038*
C4	0.5400 (3)	0.0464 (2)	0.5224 (2)	0.0300 (4)
C5	0.4858 (3)	0.1890 (3)	0.5114 (3)	0.0399 (5)
H5	0.3941	0.2288	0.4771	0.048*
C6	0.5668 (3)	0.2719 (2)	0.5509 (3)	0.0392 (5)
H6	0.5280	0.3673	0.5415	0.047*
C7	0.7037 (3)	0.2197 (2)	0.6041 (2)	0.0305 (4)
C8	0.7779 (3)	0.3350 (3)	0.6322 (3)	0.0375 (5)
C9	0.7614 (3)	0.3778 (2)	0.1372 (2)	0.0328 (4)
C10	0.7227 (3)	0.2594 (2)	0.1042 (2)	0.0336 (5)
C11	0.5985 (3)	0.1497 (3)	0.0235 (3)	0.0436 (6)
H19	0.5263	0.1307	−0.0179	0.052*
C12	0.7149 (4)	0.0538 (3)	0.0759 (3)	0.0473 (6)
H20	0.7368	−0.0416	0.0771	0.057*
C13	0.8671 (3)	0.5175 (3)	0.2050 (3)	0.0440 (6)
H21	0.9329	0.5524	0.2414	0.053*
C14	0.7403 (3)	0.5901 (3)	0.1520 (3)	0.0436 (6)
H22	0.7041	0.6853	0.1456	0.052*
N1	0.7933 (3)	0.1248 (2)	0.1265 (2)	0.0406 (4)
H1A	0.8659	0.0821	0.1742	0.049*
N2	0.6044 (3)	0.2788 (2)	0.0414 (2)	0.0366 (4)
N3	0.6732 (2)	0.5025 (2)	0.1091 (2)	0.0372 (4)
N4	0.8794 (3)	0.3831 (2)	0.1946 (2)	0.0402 (4)
H4A	0.9538	0.3110	0.2211	0.048*
O1	0.9901 (3)	0.0489 (2)	0.7164 (3)	0.0592 (5)
O2	0.9025 (2)	−0.15120 (19)	0.7137 (2)	0.0528 (5)
O3	0.9163 (3)	0.3100 (2)	0.6670 (3)	0.0576 (5)
O4	0.7063 (3)	0.4532 (2)	0.6186 (2)	0.0536 (5)
O1W	0.2826 (2)	0.4101 (2)	0.2126 (2)	0.0517 (5)
H1W	0.2680	0.4378	0.2782	0.078*
H2W	0.2367	0.3277	0.2477	0.078*
H3A	0.962 (5)	0.217 (2)	0.673 (5)	0.100 (13)*

	U11	U22	U33	U12	U13	U23
Zn1	0.0416 (2)	0.0294 (2)	0.0549 (3)	0.00961 (15)	−0.03317 (18)	−0.01971 (17)
C1	0.0359 (11)	0.0351 (11)	0.0469 (12)	0.0071 (9)	−0.0249 (10)	−0.0197 (10)
C2	0.0321 (10)	0.0270 (10)	0.0351 (10)	0.0038 (8)	−0.0184 (9)	−0.0129 (8)
C3	0.0346 (11)	0.0260 (10)	0.0424 (11)	0.0073 (8)	−0.0229 (9)	−0.0155 (9)
C4	0.0355 (11)	0.0254 (10)	0.0351 (10)	0.0042 (8)	−0.0201 (9)	−0.0130 (8)
C5	0.0489 (13)	0.0323 (11)	0.0604 (14)	0.0156 (10)	−0.0411 (12)	−0.0242 (11)
C6	0.0502 (13)	0.0280 (11)	0.0542 (13)	0.0122 (10)	−0.0320 (11)	−0.0220 (10)
C7	0.0349 (11)	0.0284 (10)	0.0343 (10)	0.0029 (8)	−0.0174 (9)	−0.0152 (8)
C8	0.0452 (13)	0.0319 (11)	0.0446 (12)	0.0026 (9)	−0.0226 (10)	−0.0195 (10)
C9	0.0317 (10)	0.0327 (11)	0.0402 (11)	0.0070 (8)	−0.0200 (9)	−0.0166 (9)
C10	0.0349 (11)	0.0291 (10)	0.0396 (11)	0.0059 (8)	−0.0182 (9)	−0.0145 (9)
C11	0.0566 (15)	0.0321 (11)	0.0559 (14)	0.0036 (10)	−0.0337 (12)	−0.0201 (11)
C12	0.0608 (16)	0.0309 (12)	0.0636 (16)	0.0106 (11)	−0.0330 (13)	−0.0253 (11)
C13	0.0460 (13)	0.0461 (14)	0.0579 (15)	0.0050 (11)	−0.0316 (12)	−0.0281 (12)
C14	0.0490 (14)	0.0380 (12)	0.0640 (15)	0.0105 (10)	−0.0332 (12)	−0.0308 (12)
N1	0.0456 (11)	0.0326 (10)	0.0545 (12)	0.0137 (8)	−0.0324 (10)	−0.0192 (9)
N2	0.0418 (10)	0.0300 (9)	0.0489 (11)	0.0083 (8)	−0.0282 (9)	−0.0181 (8)
N3	0.0394 (10)	0.0347 (10)	0.0532 (11)	0.0105 (8)	−0.0302 (9)	−0.0233 (9)
N4	0.0394 (10)	0.0393 (10)	0.0552 (12)	0.0115 (8)	−0.0315 (9)	−0.0223 (9)
O1	0.0659 (12)	0.0518 (11)	0.1051 (16)	0.0251 (9)	−0.0670 (12)	−0.0479 (11)
O2	0.0539 (11)	0.0330 (9)	0.0920 (14)	0.0141 (8)	−0.0539 (11)	−0.0248 (9)
O3	0.0620 (12)	0.0441 (10)	0.1003 (15)	0.0128 (9)	−0.0549 (12)	−0.0412 (11)
O4	0.0706 (12)	0.0399 (10)	0.0807 (13)	0.0161 (9)	−0.0472 (11)	−0.0387 (9)
O1W	0.0637 (12)	0.0427 (9)	0.0564 (11)	−0.0089 (8)	−0.0204 (9)	−0.0268 (8)

Zn1—O1W	2.135 (2)	C8—O3	1.288 (3)
Zn1—O1Wi	2.135 (2)	C9—N3	1.326 (3)
Zn1—N3i	2.1419 (18)	C9—N4	1.334 (3)
Zn1—N3	2.1419 (18)	C9—C10	1.445 (3)
Zn1—N2i	2.1625 (19)	C10—N2	1.321 (3)
Zn1—N2	2.1625 (19)	C10—N1	1.341 (3)
C1—O2	1.231 (3)	C11—C12	1.358 (4)
C1—O1	1.258 (3)	C11—N2	1.368 (3)
C1—C2	1.528 (3)	C11—H19	0.9300
C2—C3	1.395 (3)	C12—N1	1.364 (3)
C2—C7	1.411 (3)	C12—H20	0.9300
C3—C4	1.392 (3)	C13—C14	1.351 (4)
C3—H3	0.9300	C13—N4	1.361 (3)
C4—C5	1.390 (3)	C13—H21	0.9300
C4—C4ii	1.490 (4)	C14—N3	1.370 (3)
C5—C6	1.376 (3)	C14—H22	0.9300
C5—H5	0.9300	N1—H1A	0.8755
C6—C7	1.391 (3)	N4—H4A	0.9008
C6—H6	0.9300	O3—H3A	0.93 (3)
C7—C8	1.522 (3)	O1W—H1W	0.8119
C8—O4	1.217 (3)	O1W—H2W	0.7930
O1W—Zn1—O1Wi	180.00 (10)	O4—C8—C7	119.0 (2)
O1W—Zn1—N3i	88.19 (8)	O3—C8—C7	120.8 (2)
O1Wi—Zn1—N3i	91.81 (8)	N3—C9—N4	111.41 (19)
O1W—Zn1—N3	91.81 (8)	N3—C9—C10	119.57 (19)
O1Wi—Zn1—N3	88.19 (8)	N4—C9—C10	129.0 (2)
N3i—Zn1—N3	180.0	N2—C10—N1	111.27 (19)
O1W—Zn1—N2i	87.51 (8)	N2—C10—C9	119.67 (19)
O1Wi—Zn1—N2i	92.49 (8)	N1—C10—C9	129.1 (2)
N3i—Zn1—N2i	79.56 (7)	C12—C11—N2	109.2 (2)
N3—Zn1—N2i	100.44 (7)	C12—C11—H19	125.4
O1W—Zn1—N2	92.49 (8)	N2—C11—H19	125.4
O1Wi—Zn1—N2	87.51 (8)	C11—C12—N1	106.6 (2)
N3i—Zn1—N2	100.44 (7)	C11—C12—H20	126.7
N3—Zn1—N2	79.56 (7)	N1—C12—H20	126.7
N2i—Zn1—N2	180.0	C14—C13—N4	106.3 (2)
O2—C1—O1	122.0 (2)	C14—C13—H21	126.8
O2—C1—C2	117.98 (19)	N4—C13—H21	126.8
O1—C1—C2	120.0 (2)	C13—C14—N3	109.8 (2)
C3—C2—C7	118.34 (19)	C13—C14—H22	125.1
C3—C2—C1	113.56 (18)	N3—C14—H22	125.1
C7—C2—C1	128.06 (18)	C10—N1—C12	107.05 (19)
C4—C3—C2	123.86 (19)	C10—N1—H1A	128.5
C4—C3—H3	118.1	C12—N1—H1A	124.1
C2—C3—H3	118.1	C10—N2—C11	105.86 (19)
C5—C4—C3	116.66 (19)	C10—N2—Zn1	110.26 (14)
C5—C4—C4ii	122.8 (2)	C11—N2—Zn1	143.84 (16)
C3—C4—C4ii	120.6 (2)	C9—N3—C14	105.05 (18)
C6—C5—C4	120.6 (2)	C9—N3—Zn1	110.75 (14)
C6—C5—H5	119.7	C14—N3—Zn1	143.92 (16)
C4—C5—H5	119.7	C9—N4—C13	107.4 (2)
C5—C6—C7	123.1 (2)	C9—N4—H4A	126.2
C5—C6—H6	118.5	C13—N4—H4A	126.4
C7—C6—H6	118.5	C8—O3—H3A	113 (3)
C6—C7—C2	117.43 (18)	Zn1—O1W—H1W	121.7
C6—C7—C8	113.31 (18)	Zn1—O1W—H2W	121.9
C2—C7—C8	129.25 (19)	H1W—O1W—H2W	111.7
O4—C8—O3	120.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1iii	0.88	1.94	2.802 (3)	169
N4—H4A···O2iii	0.90	1.89	2.791 (3)	176
O1W—H1W···O4iv	0.81	1.90	2.683 (2)	162
O1W—H2W···O2ii	0.79	1.98	2.751 (3)	164
O3—H3A···O1	0.93 (3)	1.52 (3)	2.434 (3)	165 (4)

Table 1

Selected bond lengths (Å)

Zn1—O1W	2.135 (2)
Zn1—N3	2.1419 (18)
Zn1—N2	2.1625 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	1.94	2.802 (3)	169
N4—H4A⋯O2i	0.90	1.89	2.791 (3)	176
O1W—H1W⋯O4ii	0.81	1.90	2.683 (2)	162
O1W—H2W⋯O2iii	0.79	1.98	2.751 (3)	164
O3—H3A⋯O1	0.93 (3)	1.52 (3)	2.434 (3)	165 (4)

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