catena-Poly[[[tetra-aqua-zinc(II)]-μ-1,4-bis-(1,2,4-triazol-1-yl)butane-κN:N] biphenyl-4,4'-dicarboxyl-ate].

The asymmetric unit of the polymeric title compound, {[Zn(C(8)H(12)N(6))(H(2)O)(4)](C(14)H(8)O(4))}(n) or {[Zn(BTB)(H(2)O)(4)](BPDC)}(n) [BTB is 1,4-bis-(1,2,4-triazol-1-yl)butane and H(2)BPDC is biphenyl-4,4'-dicarb-oxy-lic acid], contains half a [Zn(BTB)(H(2)O)(4)](2+) cation and half a BPDC anion, both ions lying about a crystallographic inversion centre. The crystal structure consists of zigzag polymeric cationic chains parallel to the c axis and uncoordinated anions linked into a three-dimensional supra-molecular architecture by O-H⋯O, C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For general background to the structures and applications of supra­molecular compounds, see: Kitagawa et al. (2004 ▶); Ferey et al. (2005 ▶); Roy et al. (2009 ▶); Zhang et al. (2009 ▶). For related compounds based on 1,4-bis­(1,2,4-triazol-1-yl)butane, see: Liu et al. (2008 ▶); Gu et al. (2008 ▶); Wang et al. (2008 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

[Zn(C8H12N6)(H2O)4](C14H8O4)

M = 569.89

Triclinic,

a = 6.4344 (15) Å

b = 7.1490 (18) Å

c = 13.539 (3) Å

α = 89.250 (4)°

β = 81.348 (4)°

γ = 72.620 (3)°

V = 587.3 (2) Å3

Z = 1

Mo Kα radiation

μ = 1.11 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.792, T max = 0.828

3162 measured reflections

2299 independent reflections

1788 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.080

S = 0.92

2237 reflections

169 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003970X/rz2494sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003970X/rz2494Isup2.hkl

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

[Zn(C8H12N6)(H2O)4](C14H8O4)	Z = 1
Mr = 569.89	F(000) = 296
Triclinic, P1	Dx = 1.611 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4344 (15) Å	Cell parameters from 1152 reflections
b = 7.1490 (18) Å	θ = 3.0–25.0°
c = 13.539 (3) Å	µ = 1.11 mm−1
α = 89.250 (4)°	T = 293 K
β = 81.348 (4)°	Block, white
γ = 72.620 (3)°	0.21 × 0.19 × 0.17 mm
V = 587.3 (2) Å3

Bruker SMART APEX CCD diffractometer	2299 independent reflections
Radiation source: fine-focus sealed tube	1788 reflections with I > 2σ(I)
graphite	Rint = 0.032
phi and ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→7
Tmin = 0.792, Tmax = 0.828	k = −6→8
3162 measured reflections	l = −16→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0317P)2] where P = (Fo2 + 2Fc2)/3
2237 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.31 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	0.1236 (5)	0.0898 (4)	0.1819 (2)	0.0408 (7)
H1A	0.0180	0.1181	0.1395	0.049*
C2	0.4301 (4)	−0.0006 (4)	0.23078 (18)	0.0323 (6)
H2A	0.5802	−0.0473	0.2337	0.039*
C3	0.2822 (4)	0.0747 (4)	0.41485 (17)	0.0347 (7)
H3A	0.1835	0.0101	0.4519	0.042*
H3B	0.2282	0.2125	0.4350	0.042*
C4	0.5070 (4)	−0.0100 (4)	0.44352 (17)	0.0311 (6)
H4A	0.6059	0.0584	0.4103	0.037*
H4B	0.5653	−0.1473	0.4224	0.037*
C5	0.1402 (5)	0.5973 (4)	0.18630 (19)	0.0319 (6)
C6	0.2502 (4)	0.5703 (4)	0.27840 (17)	0.0275 (6)
C7	0.1272 (4)	0.6255 (4)	0.37179 (19)	0.0375 (7)
H7	−0.0245	0.6825	0.3773	0.045*
C8	0.2241 (4)	0.5981 (4)	0.45708 (19)	0.0367 (7)
H8	0.1358	0.6366	0.5187	0.044*
C9	0.4489 (4)	0.5149 (3)	0.45388 (17)	0.0262 (6)
C10	0.5721 (4)	0.4649 (4)	0.35941 (19)	0.0389 (7)
H10	0.7243	0.4120	0.3534	0.047*
C11	0.4747 (5)	0.4915 (4)	0.27460 (19)	0.0393 (7)
H11	0.5629	0.4552	0.2128	0.047*
N1	0.3416 (3)	0.0186 (3)	0.14818 (15)	0.0333 (6)
N2	0.0731 (4)	0.1156 (3)	0.27853 (16)	0.0416 (6)
N3	0.2730 (4)	0.0566 (3)	0.30894 (15)	0.0299 (5)
O1	0.6429 (3)	0.2192 (3)	0.04395 (12)	0.0405 (5)
H1C	0.5383	0.3192	0.0681	0.049*
H1D	0.7103	0.2541	−0.0085	0.049*
O2	0.2224 (3)	0.2334 (3)	−0.02699 (13)	0.0459 (5)
H2C	0.2093	0.2385	−0.0886	0.055*
H2D	0.2284	0.3433	−0.0065	0.055*
O3	0.2593 (3)	0.5246 (3)	0.10408 (13)	0.0407 (5)
O4	−0.0583 (3)	0.6896 (3)	0.19568 (13)	0.0484 (6)
Zn1	0.5000	0.0000	0.0000	0.03341 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0328 (18)	0.0533 (19)	0.0323 (16)	−0.0054 (14)	−0.0083 (13)	0.0027 (13)
C2	0.0283 (15)	0.0366 (16)	0.0266 (14)	−0.0028 (13)	−0.0014 (12)	0.0002 (12)
C3	0.0380 (17)	0.0397 (16)	0.0211 (14)	−0.0057 (13)	0.0000 (12)	−0.0039 (12)
C4	0.0349 (16)	0.0298 (15)	0.0243 (14)	−0.0051 (12)	−0.0007 (12)	−0.0001 (11)
C5	0.0369 (18)	0.0294 (15)	0.0293 (15)	−0.0086 (13)	−0.0078 (13)	0.0016 (11)
C6	0.0302 (15)	0.0275 (14)	0.0246 (13)	−0.0069 (12)	−0.0072 (11)	0.0009 (11)
C7	0.0236 (15)	0.0506 (18)	0.0302 (15)	0.0012 (13)	−0.0049 (12)	0.0033 (13)
C8	0.0284 (16)	0.0504 (18)	0.0238 (14)	−0.0026 (13)	0.0000 (12)	0.0025 (12)
C9	0.0246 (15)	0.0250 (14)	0.0285 (14)	−0.0058 (11)	−0.0057 (11)	0.0005 (11)
C10	0.0222 (15)	0.0561 (19)	0.0311 (15)	−0.0005 (13)	−0.0045 (12)	−0.0085 (13)
C11	0.0314 (17)	0.0554 (19)	0.0238 (14)	−0.0041 (14)	0.0008 (12)	−0.0086 (12)
N1	0.0317 (14)	0.0398 (14)	0.0238 (12)	−0.0028 (11)	−0.0058 (10)	0.0009 (10)
N2	0.0296 (14)	0.0589 (16)	0.0300 (13)	−0.0044 (12)	−0.0035 (11)	0.0003 (11)
N3	0.0286 (13)	0.0324 (13)	0.0247 (11)	−0.0038 (10)	−0.0027 (10)	−0.0013 (9)
O1	0.0406 (12)	0.0466 (12)	0.0289 (10)	−0.0073 (10)	0.0000 (9)	−0.0030 (9)
O2	0.0524 (13)	0.0422 (12)	0.0344 (11)	0.0043 (10)	−0.0178 (9)	−0.0028 (9)
O3	0.0408 (12)	0.0480 (12)	0.0257 (10)	−0.0010 (10)	−0.0059 (9)	−0.0036 (9)
O4	0.0322 (12)	0.0707 (15)	0.0306 (11)	0.0062 (11)	−0.0125 (9)	−0.0015 (10)
Zn1	0.0329 (3)	0.0407 (3)	0.0206 (2)	−0.0017 (2)	−0.00443 (19)	−0.00010 (19)

C1—N2	1.301 (3)	C7—H7	0.9300
C1—N1	1.350 (3)	C8—C9	1.384 (4)
C1—H1A	0.9300	C8—H8	0.9300
C2—N1	1.317 (3)	C9—C10	1.389 (3)
C2—N3	1.323 (3)	C9—C9ii	1.481 (5)
C2—H2A	0.9300	C10—C11	1.374 (4)
C3—N3	1.453 (3)	C10—H10	0.9300
C3—C4	1.500 (4)	C11—H11	0.9300
C3—H3A	0.9700	N1—Zn1	2.096 (2)
C3—H3B	0.9700	N2—N3	1.354 (3)
C4—C4i	1.524 (5)	O1—Zn1	2.1693 (19)
C4—H4A	0.9700	O1—H1C	0.8500
C4—H4B	0.9700	O1—H1D	0.8499
C5—O4	1.238 (3)	O2—Zn1	2.1234 (18)
C5—O3	1.272 (3)	O2—H2C	0.8500
C5—C6	1.507 (4)	O2—H2D	0.8500
C6—C11	1.378 (4)	Zn1—N1iii	2.096 (2)
C6—C7	1.381 (3)	Zn1—O2iii	2.1234 (18)
C7—C8	1.378 (4)	Zn1—O1iii	2.1693 (19)
N2—C1—N1	114.6 (3)	C11—C10—H10	119.2
N2—C1—H1A	122.7	C9—C10—H10	119.2
N1—C1—H1A	122.7	C10—C11—C6	122.0 (2)
N1—C2—N3	109.7 (2)	C10—C11—H11	119.0
N1—C2—H2A	125.1	C6—C11—H11	119.0
N3—C2—H2A	125.1	C2—N1—C1	103.1 (2)
N3—C3—C4	114.8 (2)	C2—N1—Zn1	128.25 (18)
N3—C3—H3A	108.6	C1—N1—Zn1	127.55 (18)
C4—C3—H3A	108.6	C1—N2—N3	102.5 (2)
N3—C3—H3B	108.6	C2—N3—N2	110.0 (2)
C4—C3—H3B	108.6	C2—N3—C3	131.7 (2)
H3A—C3—H3B	107.5	N2—N3—C3	118.2 (2)
C3—C4—C4i	109.7 (3)	Zn1—O1—H1C	108.1
C3—C4—H4A	109.7	Zn1—O1—H1D	107.9
C4i—C4—H4A	109.7	H1C—O1—H1D	107.4
C3—C4—H4B	109.7	Zn1—O2—H2C	111.6
C4i—C4—H4B	109.7	Zn1—O2—H2D	111.7
H4A—C4—H4B	108.2	H2C—O2—H2D	109.6
O4—C5—O3	124.7 (2)	N1iii—Zn1—N1	180.00 (5)
O4—C5—C6	118.0 (2)	N1iii—Zn1—O2	93.74 (8)
O3—C5—C6	117.3 (2)	N1—Zn1—O2	86.26 (8)
C11—C6—C7	116.7 (2)	N1iii—Zn1—O2iii	86.26 (8)
C11—C6—C5	122.7 (2)	N1—Zn1—O2iii	93.74 (8)
C7—C6—C5	120.6 (2)	O2—Zn1—O2iii	180.00 (9)
C8—C7—C6	121.5 (2)	N1iii—Zn1—O1	93.19 (8)
C8—C7—H7	119.3	N1—Zn1—O1	86.81 (8)
C6—C7—H7	119.3	O2—Zn1—O1	87.85 (8)
C7—C8—C9	122.0 (2)	O2iii—Zn1—O1	92.15 (8)
C7—C8—H8	119.0	N1iii—Zn1—O1iii	86.81 (8)
C9—C8—H8	119.0	N1—Zn1—O1iii	93.19 (8)
C8—C9—C10	116.1 (2)	O2—Zn1—O1iii	92.15 (8)
C8—C9—C9ii	121.5 (3)	O2iii—Zn1—O1iii	87.85 (8)
C10—C9—C9ii	122.4 (3)	O1—Zn1—O1iii	180.00 (10)
C11—C10—C9	121.7 (2)
N3—C3—C4—C4i	−177.5 (3)	N2—C1—N1—C2	0.1 (3)
O4—C5—C6—C11	−171.9 (3)	N2—C1—N1—Zn1	−168.61 (19)
O3—C5—C6—C11	7.6 (4)	N1—C1—N2—N3	0.0 (3)
O4—C5—C6—C7	7.9 (4)	N1—C2—N3—N2	0.2 (3)
O3—C5—C6—C7	−172.7 (2)	N1—C2—N3—C3	−176.2 (2)
C11—C6—C7—C8	−1.7 (4)	C1—N2—N3—C2	−0.1 (3)
C5—C6—C7—C8	178.6 (2)	C1—N2—N3—C3	176.9 (2)
C6—C7—C8—C9	0.3 (4)	C4—C3—N3—C2	−9.0 (4)
C7—C8—C9—C10	1.5 (4)	C4—C3—N3—N2	174.8 (2)
C7—C8—C9—C9ii	−179.6 (3)	C2—N1—Zn1—O2	−141.6 (2)
C8—C9—C10—C11	−1.8 (4)	C1—N1—Zn1—O2	24.4 (2)
C9ii—C9—C10—C11	179.3 (3)	C2—N1—Zn1—O2iii	38.4 (2)
C9—C10—C11—C6	0.4 (5)	C1—N1—Zn1—O2iii	−155.6 (2)
C7—C6—C11—C10	1.3 (4)	C2—N1—Zn1—O1	−53.5 (2)
C5—C6—C11—C10	−178.9 (3)	C1—N1—Zn1—O1	112.5 (2)
N3—C2—N1—C1	−0.2 (3)	C2—N1—Zn1—O1iii	126.5 (2)
N3—C2—N1—Zn1	168.47 (17)	C1—N1—Zn1—O1iii	−67.5 (2)

Cg is the centroid of the C6–C11 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4iv	0.93	2.50	3.342 (3)	150
O1—H1D···O3v	0.85	2.07	2.825 (3)	148
O1—H1C···O3	0.85	1.95	2.783 (2)	167
O2—H2C···O4vi	0.85	1.85	2.642 (3)	155
O2—H2D···O3	0.85	2.06	2.839 (3)	151
C3—H3B···Cg	0.97	2.82	3.552 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C6–C11 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4i	0.93	2.50	3.342 (3)	150
O1—H1D⋯O3ii	0.85	2.07	2.825 (3)	148
O1—H1C⋯O3	0.85	1.95	2.783 (2)	167
O2—H2C⋯O4iii	0.85	1.85	2.642 (3)	155
O2—H2D⋯O3	0.85	2.06	2.839 (3)	151
C3—H3B⋯Cg	0.97	2.82	3.552 (3)	133

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