Tetra­aqua­bis(4,4′-bipyridine)zinc(II) bis­(trans-4-hydroxy­cinnamate)

Chen, L.

doi:10.1107/S1600536809023204

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m807

doi:10.1107/S1600536809023204

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Tetraaquabis(4,4′-bipyridine)zinc(II) bis(trans-4-hydroxycinnamate)

Ling Chen ^a ^*

^aCollege of Chemical Engineering and Pharmacy, Jinhua College of Profession and Technology, Jinhua, Zhejiang 321017, People's Republic of China
^*Correspondence e-mail: chenling78@126.com

(Received 11 June 2009; accepted 16 June 2009; online 20 June 2009)

The title complex, [Zn(C₁₀H₈N₂)₂(H₂O)₄](C₉H₇O₃)₂, was obtained by the hydrothermal reaction of zinc sulfate with mixed 4-hydroxylcinnamic acid (H₂L) and 4,4′-bipyridine (4,4′-bipy) ligands. The complex consists of a centrosymmetric [Zn(4,4′-bipy)₂(H₂O)₄]²⁺ cation with the metal centre in a distorted ZnN₂O₄ coordination, and of two HL⁻ anions. Extensive O—H⋯O and O—H⋯N hydrogen-bonding interactions between the constituents lead to the formation of a three-dimensional network.

Related literature

The main strategy used in the design and synthesis of novel coordination architectures is the building-block approach, see: Han et al. (2005 ); Wen et al. (2005 ); Yaghi et al. (1998 ). For the isostructural nickel analog, see: Zhou et al. (2006 ).

Experimental

Crystal data

[Zn(C₁₀H₈N₂)₂(H₂O)₄](C₉H₇O₃)₂
M_r = 776.09
Triclinic, $[P \overline 1]$
a = 7.0884 (4) Å
b = 7.3966 (4) Å
c = 17.2518 (10) Å
α = 86.972 (3)°
β = 83.872 (3)°
γ = 81.937 (3)°
V = 889.80 (9) Å³
Z = 1
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 K
0.38 × 0.19 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.84, T_max = 0.93
12766 measured reflections
4058 independent reflections
3831 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.080
S = 1.03
4058 reflections
256 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3	0.818 (15)	1.948 (16)	2.7549 (15)	169 (2)
O1W—H1WB⋯O3ⁱ	0.835 (14)	1.875 (15)	2.7069 (14)	174 (2)
O1—H1⋯N1ⁱⁱ	0.824 (17)	1.97 (2)	2.714 (2)	150 (3)
O2W—H2WA⋯O2ⁱⁱⁱ	0.834 (14)	1.869 (15)	2.6833 (14)	165.0 (19)
O2W—H2WB⋯O2^iv	0.823 (14)	1.919 (15)	2.7307 (15)	168.3 (19)
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+2, -y+1, -z; (iii) x, y+1, z; (iv) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023204/at2810sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023204/at2810Isup2.hkl

checkCIF report

Comment top

The main strategy widely used in design and synthesis of novel coordination architectures is the building-block approach (Yaghi et al., 1998; Han et al., 2005; Wen et al., 2005). 4-Hydroxylcinnamic acid (H₂L) is considered as suitable multidentate ligand is based on the following considerations: (a) It has multiple coordination sites, carboxylate group and phenolic hydroxyl group, that may generate structures of higher dimensions. (b) Hydroxyl group can also introduce hydrogen bond in the framework construction. Here, we combined H₂L and auxiliary ligand 4,4-bipy as a mixed ligand system to react metal ions. A new Zn(II) complex, [Zn(4,4'-bipy)₂(H₂O)₄].2HL, (I), was obtained unexpected. In this complex, HL ligand is non-coordinated and acts as a dissociative anion.

The X-ray diffraction study shows that the asymmetric unit of (I) is composed of half a Zn atom, one 4,4'-bipy ligand, two coordinated water molecules and one HL ligand. As shown in Fig.1, the Zn^II center is six-coordinated by four water molecules and two N atoms of 4,4'-bipy, and displays a slightly distorted [ZnO₄N₂] octahedral coordination geometry. Four water molecules form a relatively normal equatorial plane of the octahedron, and the Zn1 atom is located in this plane, while two N atoms occupy the axial positions, with an N—Zn—N angle of 180 °. The bond lengths of Zn—O_water are 2.0878 (10) and 2.0881 (10) Å, Zn—N is 2.1728 (12) Å, respectively.

There are extensive hydrogen-bonding interactions involving the HL oxygen atoms, coordinated water molecules and uncoordinated 4,4'-bipy N atoms. A three-dimensional network is formed by these hydrogen-bonding interactions, as shown in Fig. 2. Complex (I) is isostructural with its nickel analog (Zhou et al., 2006).

Related literature top

The main strategy used in the design and synthesis of novel coordination architectures is the building-block approach, see: Han et al. (2005); Wen et al. (2005); Yaghi et al. (1998). For the isostructural nickel analog, see: Zhou et al. (2006).

Experimental top

A mixture of 4-hydroxylcinnamic acid (0.1642 g, 1 mmol), ZnSO₄.7H₂O (0.1438 g, 0.5 mmol), Na₂CO₃(0.053 g, 0.5 mmol) and H₂O (15 mL) was sealed in a 25 ml stainless-steel reactor with a Telflon liner and was heated at 433 K for 3 d. On completion of the reaction, the reactor was cooled slowly to room temperature and the mixture was filtered, giving colourless single crystals suitable for X-ray analysis in yield 30% (based on Zn).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The cation and anion in (I), showing the atom-numbering scheme. Displacement ellipsoids are shown at the 30% probability level. [Symmetry code: (A) - x,1 - y,1 - z.]
	Fig. 2. The crystal packing of (I). The dashed lines indicate hydrogen-bonding interactions. H atoms have been omitted for clarity.

Tetraaquabis(4,4'-bipyridine)zinc(II) bis(trans-4-hydroxycinnamate) top

Crystal data top

[Zn(C₁₀H₈N₂)₂(H₂O)₄](C₉H₇O₃)₂	Z = 1
M_r = 776.09	F(000) = 404
Triclinic, P1	D_x = 1.448 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0884 (4) Å	Cell parameters from 7604 reflections
b = 7.3966 (4) Å	θ = 2.4–27.6°
c = 17.2518 (10) Å	µ = 0.76 mm⁻¹
α = 86.972 (3)°	T = 296 K
β = 83.872 (3)°	Block, colourless
γ = 81.937 (3)°	0.38 × 0.19 × 0.10 mm
V = 889.80 (9) Å³

Data collection top

Bruker APEXII area-detector diffractometer	4058 independent reflections
Radiation source: fine-focus sealed tube	3831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.84, T_max = 0.93	k = −9→9
12766 measured reflections	l = −22→22

Refinement top

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0476P)² + 0.2285P] where P = (F_o² + 2F_c²)/3
4058 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.25 e Å⁻³
7 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Zn(C₁₀H₈N₂)₂(H₂O)₄](C₉H₇O₃)₂	γ = 81.937 (3)°
M_r = 776.09	V = 889.80 (9) Å³
Triclinic, P1	Z = 1
a = 7.0884 (4) Å	Mo Kα radiation
b = 7.3966 (4) Å	µ = 0.76 mm⁻¹
c = 17.2518 (10) Å	T = 296 K
α = 86.972 (3)°	0.38 × 0.19 × 0.10 mm
β = 83.872 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	4058 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3831 reflections with I > 2σ(I)
T_min = 0.84, T_max = 0.93	R_int = 0.020
12766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	7 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
4058 reflections	Δρ_min = −0.33 e Å⁻³
256 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.0000	0.5000	0.5000	0.02490 (8)
N1	0.7033 (3)	0.7037 (3)	0.02925 (11)	0.0716 (6)
N2	0.15006 (17)	0.51181 (16)	0.38363 (7)	0.0286 (2)
O1W	0.04162 (15)	0.21489 (14)	0.50894 (7)	0.0353 (2)
H1WA	0.103 (3)	0.148 (3)	0.4760 (11)	0.053*
H1WB	−0.050 (2)	0.165 (3)	0.5304 (11)	0.053*
O1	1.2210 (3)	0.2418 (3)	0.12712 (9)	0.0791 (5)
H1	1.211 (4)	0.235 (4)	0.0803 (11)	0.095*
O2W	0.25236 (14)	0.50834 (15)	0.55126 (6)	0.0321 (2)
H2WA	0.302 (3)	0.600 (2)	0.5343 (12)	0.048*
H2WB	0.336 (3)	0.419 (2)	0.5482 (12)	0.048*
O2	0.44862 (15)	−0.23700 (15)	0.47767 (7)	0.0375 (2)
O3	0.24175 (14)	−0.04752 (14)	0.41292 (6)	0.0343 (2)
C1	0.8995 (2)	0.1118 (2)	0.28991 (9)	0.0364 (3)
H1A	0.8960	0.1062	0.3440	0.044*
C2	1.0548 (2)	0.1715 (2)	0.24627 (10)	0.0418 (4)
H2A	1.1535	0.2067	0.2709	0.050*
C3	1.0634 (3)	0.1792 (3)	0.16569 (10)	0.0469 (4)
C4	0.9163 (3)	0.1275 (3)	0.13005 (10)	0.0563 (5)
H4A	0.9223	0.1306	0.0759	0.068*
C5	0.7585 (3)	0.0705 (3)	0.17450 (10)	0.0472 (4)
H5A	0.6582	0.0391	0.1496	0.057*
C6	0.7480 (2)	0.0596 (2)	0.25546 (9)	0.0319 (3)
C7	0.5805 (2)	−0.0009 (2)	0.30247 (9)	0.0329 (3)
H7A	0.4696	−0.0010	0.2781	0.039*
C8	0.5768 (2)	−0.0550 (2)	0.37683 (9)	0.0320 (3)
H8A	0.6881	−0.0547	0.4009	0.038*
C9	0.40854 (19)	−0.11645 (18)	0.42536 (8)	0.0274 (3)
C10	0.5155 (4)	0.7408 (5)	0.03681 (14)	0.0983 (11)
H10A	0.4563	0.7952	−0.0058	0.118*
C11	0.4004 (3)	0.7038 (5)	0.10411 (13)	0.0830 (9)
H11A	0.2681	0.7326	0.1056	0.100*
C12	0.4808 (2)	0.6252 (2)	0.16828 (9)	0.0402 (4)
C13	0.6782 (3)	0.5875 (3)	0.16090 (13)	0.0649 (6)
H13A	0.7417	0.5348	0.2027	0.078*
C14	0.7814 (3)	0.6288 (4)	0.09087 (15)	0.0740 (7)
H14A	0.9141	0.6018	0.0874	0.089*
C15	0.3318 (2)	0.4346 (2)	0.36835 (9)	0.0320 (3)
H15A	0.3863	0.3548	0.4058	0.038*
C16	0.4417 (2)	0.4678 (2)	0.29975 (9)	0.0358 (3)
H16A	0.5680	0.4122	0.2920	0.043*
C17	0.3643 (2)	0.5841 (2)	0.24213 (9)	0.0326 (3)
C18	0.1735 (2)	0.6606 (2)	0.25723 (9)	0.0384 (3)
H18A	0.1142	0.7375	0.2200	0.046*
C19	0.0736 (2)	0.6215 (2)	0.32754 (9)	0.0364 (3)
H19A	−0.0535	0.6740	0.3366	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02173 (12)	0.02703 (12)	0.02486 (13)	−0.00473 (8)	0.00350 (8)	0.00093 (8)
N1	0.0743 (13)	0.0967 (15)	0.0436 (10)	−0.0347 (11)	0.0228 (9)	0.0019 (10)
N2	0.0265 (6)	0.0313 (6)	0.0265 (6)	−0.0037 (4)	0.0028 (4)	−0.0002 (5)
O1W	0.0317 (5)	0.0268 (5)	0.0448 (6)	−0.0058 (4)	0.0115 (5)	−0.0023 (4)
O1	0.0665 (10)	0.1314 (16)	0.0453 (8)	−0.0548 (10)	0.0178 (7)	0.0054 (9)
O2W	0.0242 (5)	0.0359 (5)	0.0356 (6)	−0.0068 (4)	0.0003 (4)	0.0042 (4)
O2	0.0299 (5)	0.0385 (6)	0.0417 (6)	−0.0061 (4)	0.0016 (4)	0.0127 (5)
O3	0.0243 (5)	0.0373 (5)	0.0387 (6)	−0.0017 (4)	0.0041 (4)	0.0032 (4)
C1	0.0344 (8)	0.0457 (8)	0.0285 (7)	−0.0089 (6)	0.0010 (6)	0.0044 (6)
C2	0.0339 (8)	0.0531 (10)	0.0391 (9)	−0.0137 (7)	0.0016 (7)	0.0024 (7)
C3	0.0435 (9)	0.0587 (11)	0.0373 (9)	−0.0166 (8)	0.0113 (7)	0.0042 (8)
C4	0.0643 (12)	0.0818 (14)	0.0253 (8)	−0.0288 (11)	0.0065 (8)	0.0044 (8)
C5	0.0474 (10)	0.0654 (11)	0.0323 (8)	−0.0232 (8)	−0.0028 (7)	0.0032 (8)
C6	0.0305 (7)	0.0342 (7)	0.0294 (7)	−0.0051 (6)	0.0034 (6)	0.0040 (6)
C7	0.0274 (7)	0.0353 (7)	0.0353 (8)	−0.0061 (6)	0.0009 (6)	0.0026 (6)
C8	0.0234 (6)	0.0355 (7)	0.0359 (8)	−0.0055 (5)	0.0020 (6)	0.0047 (6)
C9	0.0255 (6)	0.0265 (6)	0.0291 (7)	−0.0044 (5)	0.0038 (5)	−0.0013 (5)
C10	0.0731 (17)	0.179 (3)	0.0418 (12)	−0.0355 (19)	0.0030 (11)	0.0382 (17)
C11	0.0505 (12)	0.153 (3)	0.0425 (12)	−0.0225 (14)	0.0033 (9)	0.0329 (14)
C12	0.0440 (9)	0.0449 (9)	0.0303 (8)	−0.0132 (7)	0.0112 (7)	−0.0007 (6)
C13	0.0474 (11)	0.0872 (16)	0.0521 (12)	−0.0041 (10)	0.0168 (9)	0.0156 (11)
C14	0.0547 (12)	0.0988 (18)	0.0613 (14)	−0.0142 (12)	0.0271 (11)	0.0082 (13)
C15	0.0299 (7)	0.0346 (7)	0.0291 (7)	−0.0009 (6)	0.0016 (6)	0.0024 (6)
C16	0.0273 (7)	0.0430 (8)	0.0337 (8)	0.0004 (6)	0.0056 (6)	−0.0009 (6)
C17	0.0340 (7)	0.0351 (7)	0.0275 (7)	−0.0075 (6)	0.0068 (6)	−0.0015 (6)
C18	0.0377 (8)	0.0445 (8)	0.0289 (7)	0.0018 (6)	0.0020 (6)	0.0073 (6)
C19	0.0291 (7)	0.0449 (8)	0.0311 (8)	0.0029 (6)	0.0032 (6)	0.0035 (6)

Geometric parameters (Å, º) top

Zn1—O1W	2.0878 (10)	C4—H4A	0.9300
Zn1—O1Wⁱ	2.0878 (10)	C5—C6	1.389 (2)
Zn1—O2W	2.0881 (10)	C5—H5A	0.9300
Zn1—O2Wⁱ	2.0881 (10)	C6—C7	1.4740 (19)
Zn1—N2ⁱ	2.1728 (12)	C7—C8	1.322 (2)
Zn1—N2	2.1728 (12)	C7—H7A	0.9300
N1—C14	1.312 (3)	C8—C9	1.4931 (18)
N1—C10	1.314 (3)	C8—H8A	0.9300
N2—C15	1.3388 (18)	C10—C11	1.384 (3)
N2—C19	1.3396 (19)	C10—H10A	0.9300
O1W—H1WA	0.818 (15)	C11—C12	1.365 (3)
O1W—H1WB	0.835 (14)	C11—H11A	0.9300
O1—C3	1.364 (2)	C12—C13	1.381 (3)
O1—H1	0.824 (17)	C12—C17	1.484 (2)
O2W—H2WA	0.834 (14)	C13—C14	1.386 (3)
O2W—H2WB	0.823 (14)	C13—H13A	0.9300
O2—C9	1.2605 (17)	C14—H14A	0.9300
O3—C9	1.2559 (17)	C15—C16	1.376 (2)
C1—C2	1.377 (2)	C15—H15A	0.9300
C1—C6	1.390 (2)	C16—C17	1.387 (2)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.383 (2)	C17—C18	1.394 (2)
C2—H2A	0.9300	C18—C19	1.376 (2)
C3—C4	1.373 (3)	C18—H18A	0.9300
C4—C5	1.390 (2)	C19—H19A	0.9300

O1W—Zn1—O1Wⁱ	180.0	C5—C6—C7	120.99 (14)
O1W—Zn1—O2W	90.44 (4)	C1—C6—C7	121.73 (14)
O1Wⁱ—Zn1—O2W	89.56 (4)	C8—C7—C6	124.58 (14)
O1W—Zn1—O2Wⁱ	89.56 (4)	C8—C7—H7A	117.7
O1Wⁱ—Zn1—O2Wⁱ	90.44 (4)	C6—C7—H7A	117.7
O2W—Zn1—O2Wⁱ	180.0	C7—C8—C9	125.33 (14)
O1W—Zn1—N2ⁱ	86.05 (4)	C7—C8—H8A	117.3
O1Wⁱ—Zn1—N2ⁱ	93.95 (4)	C9—C8—H8A	117.3
O2W—Zn1—N2ⁱ	88.47 (4)	O3—C9—O2	124.73 (12)
O2Wⁱ—Zn1—N2ⁱ	91.53 (4)	O3—C9—C8	120.02 (13)
O1W—Zn1—N2	93.95 (4)	O2—C9—C8	115.24 (12)
O1Wⁱ—Zn1—N2	86.05 (4)	N1—C10—C11	124.1 (2)
O2W—Zn1—N2	91.53 (4)	N1—C10—H10A	117.9
O2Wⁱ—Zn1—N2	88.47 (4)	C11—C10—H10A	117.9
N2ⁱ—Zn1—N2	180.0	C12—C11—C10	120.1 (2)
C14—N1—C10	116.03 (18)	C12—C11—H11A	120.0
C15—N2—C19	117.08 (12)	C10—C11—H11A	120.0
C15—N2—Zn1	121.81 (10)	C11—C12—C13	116.05 (17)
C19—N2—Zn1	120.28 (9)	C11—C12—C17	122.30 (16)
Zn1—O1W—H1WA	124.9 (15)	C13—C12—C17	121.65 (17)
Zn1—O1W—H1WB	116.7 (14)	C12—C13—C14	119.7 (2)
H1WA—O1W—H1WB	109.5 (18)	C12—C13—H13A	120.2
C3—O1—H1	106 (2)	C14—C13—H13A	120.2
Zn1—O2W—H2WA	110.0 (14)	N1—C14—C13	124.0 (2)
Zn1—O2W—H2WB	118.7 (14)	N1—C14—H14A	118.0
H2WA—O2W—H2WB	108.1 (17)	C13—C14—H14A	118.0
C2—C1—C6	121.95 (15)	N2—C15—C16	123.05 (14)
C2—C1—H1A	119.0	N2—C15—H15A	118.5
C6—C1—H1A	119.0	C16—C15—H15A	118.5
C1—C2—C3	119.85 (16)	C15—C16—C17	120.05 (13)
C1—C2—H2A	120.1	C15—C16—H16A	120.0
C3—C2—H2A	120.1	C17—C16—H16A	120.0
O1—C3—C4	124.55 (16)	C16—C17—C18	116.86 (13)
O1—C3—C2	115.97 (17)	C16—C17—C12	121.15 (14)
C4—C3—C2	119.48 (15)	C18—C17—C12	121.99 (14)
C3—C4—C5	120.35 (16)	C19—C18—C17	119.57 (14)
C3—C4—H4A	119.8	C19—C18—H18A	120.2
C5—C4—H4A	119.8	C17—C18—H18A	120.2
C6—C5—C4	121.10 (17)	N2—C19—C18	123.35 (14)
C6—C5—H5A	119.5	N2—C19—H19A	118.3
C4—C5—H5A	119.5	C18—C19—H19A	118.3
C5—C6—C1	117.26 (14)

O1W—Zn1—N2—C15	−57.34 (12)	C14—N1—C10—C11	−0.7 (5)
O1Wⁱ—Zn1—N2—C15	122.66 (12)	N1—C10—C11—C12	0.5 (6)
O2W—Zn1—N2—C15	33.20 (12)	C10—C11—C12—C13	0.1 (4)
O2Wⁱ—Zn1—N2—C15	−146.80 (12)	C10—C11—C12—C17	179.5 (3)
O1W—Zn1—N2—C19	133.37 (12)	C11—C12—C13—C14	−0.4 (4)
O1Wⁱ—Zn1—N2—C19	−46.63 (12)	C17—C12—C13—C14	−179.8 (2)
O2W—Zn1—N2—C19	−136.08 (12)	C10—N1—C14—C13	0.4 (4)
O2Wⁱ—Zn1—N2—C19	43.92 (12)	C12—C13—C14—N1	0.2 (4)
C6—C1—C2—C3	−0.6 (3)	C19—N2—C15—C16	2.1 (2)
C1—C2—C3—O1	179.30 (18)	Zn1—N2—C15—C16	−167.54 (12)
C1—C2—C3—C4	0.2 (3)	N2—C15—C16—C17	−0.9 (2)
O1—C3—C4—C5	−178.0 (2)	C15—C16—C17—C18	−0.9 (2)
C2—C3—C4—C5	0.9 (3)	C15—C16—C17—C12	178.75 (15)
C3—C4—C5—C6	−1.8 (3)	C11—C12—C17—C16	164.8 (2)
C4—C5—C6—C1	1.4 (3)	C13—C12—C17—C16	−15.9 (3)
C4—C5—C6—C7	180.00 (17)	C11—C12—C17—C18	−15.6 (3)
C2—C1—C6—C5	−0.2 (2)	C13—C12—C17—C18	163.7 (2)
C2—C1—C6—C7	−178.80 (15)	C16—C17—C18—C19	1.3 (2)
C5—C6—C7—C8	163.73 (17)	C12—C17—C18—C19	−178.31 (16)
C1—C6—C7—C8	−17.7 (2)	C15—N2—C19—C18	−1.6 (2)
C6—C7—C8—C9	179.92 (14)	Zn1—N2—C19—C18	168.18 (13)
C7—C8—C9—O3	−32.7 (2)	C17—C18—C19—N2	−0.1 (3)
C7—C8—C9—O2	147.76 (16)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.82 (2)	1.95 (2)	2.7549 (15)	169 (2)
O1W—H1WB···O3ⁱⁱ	0.84 (1)	1.88 (2)	2.7069 (14)	174 (2)
O1—H1···N1ⁱⁱⁱ	0.82 (2)	1.97 (2)	2.714 (2)	150 (3)
O2W—H2WA···O2^iv	0.83 (1)	1.87 (2)	2.6833 (14)	165 (2)
O2W—H2WB···O2^v	0.82 (1)	1.92 (2)	2.7307 (15)	168 (2)

Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+2, −y+1, −z; (iv) x, y+1, z; (v) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₈N₂)₂(H₂O)₄](C₉H₇O₃)₂
M_r	776.09
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.0884 (4), 7.3966 (4), 17.2518 (10)
α, β, γ (°)	86.972 (3), 83.872 (3), 81.937 (3)
V (Å³)	889.80 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.38 × 0.19 × 0.10

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.84, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	12766, 4058, 3831
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.080, 1.03
No. of reflections	4058
No. of parameters	256
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.33

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.818 (15)	1.948 (16)	2.7549 (15)	169 (2)
O1W—H1WB···O3ⁱ	0.835 (14)	1.875 (15)	2.7069 (14)	174 (2)
O1—H1···N1ⁱⁱ	0.824 (17)	1.97 (2)	2.714 (2)	150 (3)
O2W—H2WA···O2ⁱⁱⁱ	0.834 (14)	1.869 (15)	2.6833 (14)	165.0 (19)
O2W—H2WB···O2^iv	0.823 (14)	1.919 (15)	2.7307 (15)	168.3 (19)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+2, −y+1, −z; (iii) x, y+1, z; (iv) −x+1, −y, −z+1.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Han, Z.-B., Cheng, X.-N. & Chen, X.-M. (2005). Cryst. Growth Des. 5, 695–700. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wen, Y.-H., Zhang, J., Wang, X.-Q., Feng, Y.-L., Cheng, J.-K., Li, Z.-J. & Yao, Y.-G. (2005). New J. Chem. 29, 995–997. Web of Science CSD CrossRef CAS Google Scholar
Yaghi, O. M., Li, H., Davis, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res. 31, 474–484. Web of Science CrossRef CAS Google Scholar
Zhou, Q.-X., Xu, Q.-F., Lu, J.-M. & Xia, X.-W. (2006). Chin. J. Struct. Chem. 25, 1392–1396. CAS Google Scholar

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Volume 65| Part 7| July 2009| Page m807

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