Poly[[(4,4′-bipyridine-κN)[μ3-(S)-2-hy­droxy­butane­dioato-κ4O1,O2:O4:O4′]zinc] dihydrate]

Lu, Y.-K.; Liu, J.; Diao, C.-L.; Lü, R.-Q.; Liu, Y.-Q.

doi:10.1107/S1600536811045788

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1684-m1685

https://doi.org/10.1107/S1600536811045788

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Poly[[(4,4′-bipyridine-κN)[μ₃-(S)-2-hydroxybutanedioato-κ⁴O¹,O²:O⁴:O^4′]zinc] dihydrate]

Yu-Kun Lu,^a ^* Jian Liu,^b Cheng-Lin Diao,^a Ren-Qing Lü ^a and Yun-Qi Liu ^a

^aState Key Laboratory of Heavy Oil Processing, College of Science, China University of Petroleum (East China), Qingdao Shandong 266555, People's Republic of China, and ^bTingyi (Cayman Islands) Holding Corporation, Tianjin 300457, People's Republic of China
^*Correspondence e-mail: lyk@upc.edu.cn

(Received 24 October 2011; accepted 31 October 2011; online 5 November 2011)

In the title compound, {[Zn(C₄H₄O₅)(C₁₀H₈N₂)]·2H₂O}_n, the Zn^II ion displays a distorted tetragonal–pyramidal coordination environment with one hydroxy O and three carboxylate O atoms from three malate anions, and the one remaining position occupied by an N atom from a 4,4′-bipyridine ligand. The pyridine rings of the 4,4′-bipyridine ligand are twisted with respect to each other by a dihedral angle of 35.8 (2)°. The uncoordinated water molecules are linked to the complex molecules by O—H⋯O hydrogen bonds. Each malate anion forms four coordination bonds with three Zn atoms, establishing a layer structure parallel to the ac plane. Adjacent layers are further linked via O—H⋯N hydrogen bonding. π–π stacking between the pyridine rings [face-to-face distance = 3.651 (3) Å] occurs in the crystal structure.

Related literature

For applications of compounds with metal-organic framework structures (MOFs), see: Rowsell & Yaghi (2005 ). For the malate ligand, see: Duan et al. (2006 ); Li et al. (2008 ); Lin & Xu (2005 ); Ou et al. (2009 ); Xie et al. (2004 ). For related structures, see: Gadzikwa et al. (2008 ); Ma et al. (2010 ); Nordell et al. (2003 ).

Experimental

Crystal data

[Zn(C₄H₄O₅)(C₁₀H₈N₂)]·2H₂O
M_r = 389.66
Orthorhombic, F d d 2
a = 17.810 (5) Å
b = 47.447 (9) Å
c = 7.4063 (15) Å
V = 6259 (2) Å³
Z = 16
Mo Kα radiation
μ = 1.61 mm⁻¹
T = 293 K
0.25 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.689, T_max = 0.843
14679 measured reflections
3380 independent reflections
2817 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.087
S = 1.09
3380 reflections
217 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1438 Friedel pairs
Flack parameter: 0.006 (17)

Table 1
Selected bond lengths (Å)

Zn1—N1	2.066 (3)
Zn1—O1	1.985 (3)
Zn1—O3	2.188 (4)
Zn1—O4ⁱ	2.031 (4)
Zn1—O5ⁱⁱ	1.999 (3)
Symmetry codes: (i) x, y, z-1; (ii) $[x+{\script{1\over 4}}, -y+{\script{1\over 4}}, z-{\script{3\over 4}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯O2ⁱ	0.86	2.22	2.730 (6)	118
O2W—H14⋯O2	0.85	2.43	2.850 (6)	111
O3—H3⋯N2ⁱⁱⁱ	0.84	2.13	2.721 (5)	127
Symmetry codes: (i) x, y, z-1; (iii) $[-x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045788/xu5364sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045788/xu5364Isup2.hkl

checkCIF report

Comment top

The design and synthesis of MOFs with original architectures, which could offer great potential for chemical and structural diversity, is one of the major current challenges in inorganic chemistry (Rowsell & Yaghi, 2005). The malate ligand, besides two terminal carboxyl groups, contains a hydroxyl group in the α-position, which can potentially provide an additional coordination site and allows the formation of five- and six-membered rings to stabilize the solid networks (Duan et al., 2006; Xie et al., 2004). In recent years, the construction of MOFs based on malate ligand has been investigated owing to their fascinating coordination modes (Li et al., 2008; Lin et al., 2005; Ou et al., 2009). Herein we report the hydrothermal synthesis and crystal structure of the tile compound.

As shown in Fig. 1, the Zn^II ion exhibits a distorted tetragonal pyramid coordination geometry, defined by one N atom from 4,4'-bipyridine molecule, one hydroxyl oxygen and three carboxylate oxygen atoms coming from three different malate ligands. The Zn1—O bond lengths fall in the range of 1.985 (3)–2.188 (4) Å, and the Zn1—N1 distance is 2.066 (3) Å, and the O—Zn—O(N) angles varying from 75.97 (12)–158.80 (11)°, thus falling in the expected region (Gadzikwa et al., 2008). The 4,4'-bipyridine ligand adopts the unidentate coordination mode and the unligated N2 atom acts as the H-bonding acceptor from the hydroxyl group [O3—H3···N2, 2.721 (5) ?] (Ma et al., 2010; Nordell et al., 2003). One carboxylate (O4—C14—O5) of malate dianion act as bidentate bridging and adopt a µ₂-η¹:η¹ coordinated mode, while the carboxyl O1 and the hydroxyl group O3 atoms chelate a Zn ion. The remaining uncoordinated carboxyl O2 atom links with lattice water molecules via O—H···O hydrogen bonding (Table 1). As a result, each malate dianion forms four coordination bonds with three Zn centers, leading to a two-dimensional layer structure parallel to the ac plane (Fig. 2).

Partially overlapped arrangement is observed between parallel pyridine rings of adjacent layers, the face-to-face separation of 3.644 Å between N1-py and N2^vii-py rings and 3.435 Å for N2-py and N1^vii-py rings, indicates the existence of π-π stacking [symmetry code: (vii) -x, 1/2 - y, 1/2 + z]. The adjacent layers are further linked via O—H···N(O) hydrogen bonds and π···π interactions, leading to the formation of a three-dimensional supramolecular framework structure (Table 1 and Fig. 3).

Related literature top

For applications of compounds with metal-organic framework structures (MOFs), see: Rowsell & Yaghi (2005). For the malate ligand, see: Duan et al. (2006); Li et al. (2008); Lin & Xu (2005); Ou et al. (2009); Xie et al. (2004). For related structures, see: Gadzikwa et al. (2008); Ma et al. (2010); Nordell et al. (2003).

Experimental top

A mixture of Zn(OAc)₂.2H₂O (0.22 g, 1.0 mmol), D,L-malic acid (0.27 g, 2.0 mmol), 4,4'-bpy (0.2 g, 1.0 mmol) and 20 ml water was stirred for 2 h in air; it was adjusted to pH = 5.0 with KOH solution (1.0 mol.L^-1) and was heated in a 30 ml stainless steel reactor with a Teflon-liner at 140°C for 3 days, and then cooled to room temperature. Colorless block crystals were isolated with 38% yield (based on Zn). Elemental analysis: Anal. Calcd: C, 43.15; H, 4.11; N, 7.19; Found: C, 42.05; H, 3.97; N, 7.22.

Structure description top

For applications of compounds with metal-organic framework structures (MOFs), see: Rowsell & Yaghi (2005). For the malate ligand, see: Duan et al. (2006); Li et al. (2008); Lin & Xu (2005); Ou et al. (2009); Xie et al. (2004). For related structures, see: Gadzikwa et al. (2008); Ma et al. (2010); Nordell et al. (2003).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecule of title compound with displacement ellipsoids drawn at the 30% probability level. [Symmetry codes: (i) x, y, -1 + z; (ii) 1/4 + x, 1/4 - y, -3/4 + z.]
	Fig. 2. Ball-and-stick representation of the two-dimensional layer structure of title compound. 4,4'-bpy molecule have been omitted for clarity.
	Fig. 3. The crystal packing of the title compound along the crystallographic a axis. Interlayer O—H···O(N) hydrogen bonds are shown as dashed lines.

Poly[[(4,4'-bipyridine-κN)[µ₃-(S)-2-hydroxybutanedioato- κ⁴O¹,O²:O⁴:O^4']zinc] dihydrate] top

Crystal data top

[Zn(C₄H₄O₅)(C₁₀H₈N₂)]·2H₂O	F(000) = 3200
M_r = 389.66	D_x = 1.654 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 14444 reflections
a = 17.810 (5) Å	θ = 3.0–27.5°
b = 47.447 (9) Å	µ = 1.61 mm⁻¹
c = 7.4063 (15) Å	T = 293 K
V = 6259 (2) Å³	Block, colorless
Z = 16	0.25 × 0.12 × 0.11 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3380 independent reflections
Radiation source: fine-focus sealed tube	2817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −22→22
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −60→61
T_min = 0.689, T_max = 0.843	l = −8→9
14679 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0226P)² + 22.1041P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3380 reflections	Δρ_max = 0.39 e Å⁻³
217 parameters	Δρ_min = −0.37 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1438 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (17)

Crystal data top

[Zn(C₄H₄O₅)(C₁₀H₈N₂)]·2H₂O	V = 6259 (2) Å³
M_r = 389.66	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 17.810 (5) Å	µ = 1.61 mm⁻¹
b = 47.447 (9) Å	T = 293 K
c = 7.4063 (15) Å	0.25 × 0.12 × 0.11 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3380 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2817 reflections with I > 2σ(I)
T_min = 0.689, T_max = 0.843	R_int = 0.077
14679 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0226P)² + 22.1041P] where P = (F_o² + 2F_c²)/3
S = 1.09	Δρ_max = 0.39 e Å⁻³
3380 reflections	Δρ_min = −0.37 e Å⁻³
217 parameters	Absolute structure: Flack (1983), 1438 Friedel pairs
1 restraint	Absolute structure parameter: 0.006 (17)

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	0.07684 (2)	0.130827 (9)	0.47984 (7)	0.02744 (12)
O1	0.0495 (2)	0.09140 (7)	0.5405 (4)	0.0404 (8)
O2	0.0317 (2)	0.05848 (6)	0.7462 (5)	0.0527 (9)
O3	0.0542 (2)	0.13206 (6)	0.7701 (5)	0.0485 (10)
H3	0.0687	0.1404	0.8642	0.073*
O4	0.06058 (15)	0.12247 (7)	1.2138 (5)	0.0333 (7)
O5	−0.06183 (15)	0.12117 (6)	1.2620 (4)	0.0342 (8)
O1W	0.0119 (3)	0.02832 (12)	0.0565 (8)	0.107 (2)
H11	0.0426	0.0271	−0.0336	0.160*
H12	−0.0276	0.0221	0.0211	0.160*
O2W	0.0295 (3)	0.02594 (13)	0.4228 (9)	0.111 (2)
H14	0.0006	0.0243	0.5139	0.167*
H13	0.0305	0.0435	0.4020	0.167*
N1	0.05148 (18)	0.17331 (6)	0.4739 (6)	0.0300 (8)
N2	−0.0363 (3)	0.31846 (8)	0.4508 (6)	0.0507 (12)
C1	−0.0156 (2)	0.18258 (9)	0.4188 (6)	0.0364 (11)
H1	−0.0505	0.1695	0.3778	0.055*
C2	−0.0353 (2)	0.21050 (9)	0.4200 (6)	0.0344 (10)
H2	−0.0830	0.2160	0.3828	0.052*
C3	0.0164 (2)	0.23059 (8)	0.4772 (7)	0.0295 (8)
C4	−0.0022 (2)	0.26103 (8)	0.4763 (7)	0.0314 (9)
C5	−0.0736 (3)	0.27109 (9)	0.5116 (7)	0.0395 (12)
H5	−0.1116	0.2587	0.5455	0.047*
C6	−0.0880 (3)	0.29946 (10)	0.4965 (9)	0.0501 (13)
H6	−0.1365	0.3057	0.5193	0.060*
C7	0.0328 (3)	0.30880 (10)	0.4207 (7)	0.0512 (14)
H7	0.0700	0.3217	0.3899	0.061*
C8	0.0521 (3)	0.28080 (10)	0.4329 (7)	0.0433 (12)
H8	0.1013	0.2752	0.4120	0.052*
C9	0.0855 (2)	0.22099 (9)	0.5339 (6)	0.0351 (11)
H9	0.1216	0.2337	0.5735	0.042*
C10	0.1010 (2)	0.19244 (9)	0.5320 (6)	0.0340 (11)
H10	0.1476	0.1863	0.5727	0.041*
C11	0.0415 (2)	0.08348 (9)	0.7015 (7)	0.0331 (10)
C12	0.0483 (3)	0.10540 (10)	0.8520 (6)	0.0307 (10)
H4	0.0942	0.1017	0.9209	0.037*
C13	−0.0179 (2)	0.10388 (9)	0.9781 (7)	0.0347 (9)
H13A	−0.0317	0.0842	0.9935	0.042*
H13B	−0.0601	0.1134	0.9217	0.042*
C14	−0.0056 (2)	0.11663 (8)	1.1619 (5)	0.0271 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0306 (2)	0.0257 (2)	0.0260 (2)	0.0010 (2)	0.0027 (2)	0.0005 (2)
O1	0.063 (2)	0.0302 (18)	0.0277 (17)	−0.0110 (15)	0.0055 (15)	−0.0037 (13)
O2	0.087 (2)	0.0255 (15)	0.045 (2)	−0.0076 (16)	0.024 (2)	−0.0019 (17)
O3	0.087 (3)	0.0272 (18)	0.032 (2)	−0.0112 (16)	0.0227 (19)	−0.0076 (14)
O4	0.0286 (12)	0.0465 (16)	0.0248 (16)	−0.0048 (14)	0.0006 (16)	0.0045 (16)
O5	0.0312 (14)	0.0401 (16)	0.031 (2)	0.0001 (13)	0.0052 (14)	−0.0037 (14)
O1W	0.108 (4)	0.121 (5)	0.091 (4)	−0.012 (4)	−0.006 (3)	0.054 (3)
O2W	0.092 (4)	0.126 (5)	0.115 (5)	−0.006 (3)	0.004 (3)	−0.073 (4)
N1	0.0365 (18)	0.0225 (17)	0.0311 (19)	−0.0019 (13)	0.006 (2)	−0.0032 (19)
N2	0.079 (3)	0.029 (2)	0.044 (3)	0.012 (2)	−0.005 (3)	0.0018 (19)
C1	0.036 (2)	0.030 (2)	0.043 (3)	−0.0017 (18)	−0.005 (2)	−0.0042 (19)
C2	0.027 (2)	0.032 (2)	0.045 (3)	0.0046 (17)	−0.0037 (19)	−0.0008 (19)
C3	0.036 (2)	0.0235 (19)	0.029 (2)	0.0020 (16)	0.003 (2)	0.004 (2)
C4	0.039 (2)	0.030 (2)	0.025 (2)	0.0064 (18)	−0.005 (2)	0.003 (2)
C5	0.042 (2)	0.036 (2)	0.041 (3)	0.005 (2)	0.000 (2)	0.005 (2)
C6	0.056 (3)	0.043 (3)	0.051 (3)	0.016 (2)	−0.001 (3)	0.002 (3)
C7	0.071 (4)	0.030 (2)	0.053 (3)	−0.008 (2)	0.002 (3)	0.009 (2)
C8	0.045 (3)	0.035 (2)	0.050 (3)	−0.001 (2)	0.004 (2)	0.011 (2)
C9	0.034 (2)	0.029 (2)	0.042 (3)	−0.0037 (19)	−0.004 (2)	−0.0006 (18)
C10	0.030 (2)	0.032 (2)	0.040 (3)	0.0032 (18)	0.0009 (19)	0.0013 (18)
C11	0.036 (2)	0.027 (2)	0.036 (3)	−0.0009 (17)	0.008 (2)	−0.0012 (19)
C12	0.036 (2)	0.028 (2)	0.028 (2)	−0.0003 (18)	0.0056 (19)	−0.0011 (17)
C13	0.033 (2)	0.041 (2)	0.029 (2)	−0.0020 (17)	0.003 (2)	−0.010 (2)
C14	0.033 (2)	0.025 (2)	0.0231 (19)	−0.0028 (17)	−0.0004 (17)	0.0015 (16)

Geometric parameters (Å, º) top

Zn1—N1	2.066 (3)	C2—C3	1.392 (6)
Zn1—O1	1.985 (3)	C2—H2	0.9300
Zn1—O3	2.188 (4)	C3—C9	1.378 (6)
Zn1—O4ⁱ	2.031 (4)	C3—C4	1.482 (5)
Zn1—O5ⁱⁱ	1.999 (3)	C4—C5	1.383 (6)
O1—C11	1.257 (6)	C4—C8	1.385 (6)
O2—C11	1.244 (5)	C5—C6	1.375 (6)
O3—C12	1.407 (5)	C5—H5	0.9300
O3—H3	0.8427	C6—H6	0.9300
O4—C14	1.270 (5)	C7—C8	1.375 (7)
O5—C14	1.265 (5)	C7—H7	0.9300
O1W—H11	0.8645	C8—H8	0.9300
O1W—H12	0.8063	C9—C10	1.383 (6)
O2W—H14	0.8528	C9—H9	0.9300
O2W—H13	0.8466	C10—H10	0.9300
N1—C10	1.337 (5)	C11—C12	1.529 (6)
N1—C1	1.337 (5)	C12—C13	1.506 (6)
N2—C7	1.331 (7)	C12—H4	0.9800
N2—C6	1.333 (6)	C13—C14	1.506 (6)
C1—C2	1.371 (6)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700

O1—Zn1—O5ⁱⁱ	99.87 (13)	C6—C5—H5	120.2
O1—Zn1—O4ⁱ	90.04 (13)	C4—C5—H5	120.2
O5ⁱⁱ—Zn1—O4ⁱ	104.34 (12)	N2—C6—C5	123.7 (5)
O1—Zn1—N1	150.56 (13)	N2—C6—H6	118.2
O5ⁱⁱ—Zn1—N1	105.40 (12)	C5—C6—H6	118.2
O4ⁱ—Zn1—N1	97.97 (16)	N2—C7—C8	123.6 (5)
O1—Zn1—O3	75.97 (12)	N2—C7—H7	118.2
O5ⁱⁱ—Zn1—O3	93.84 (15)	C8—C7—H7	118.2
O4ⁱ—Zn1—O3	158.80 (11)	C7—C8—C4	119.7 (5)
N1—Zn1—O3	87.40 (15)	C7—C8—H8	120.2
C11—O1—Zn1	121.6 (3)	C4—C8—H8	120.2
C12—O3—Zn1	114.4 (3)	C3—C9—C10	120.0 (4)
C12—O3—H3	95.2	C3—C9—H9	120.0
Zn1—O3—H3	140.2	C10—C9—H9	120.0
C14—O4—Zn1ⁱⁱⁱ	117.9 (3)	N1—C10—C9	122.5 (4)
C14—O5—Zn1^iv	135.0 (3)	N1—C10—H10	118.8
H11—O1W—H12	106.0	C9—C10—H10	118.8
H14—O2W—H13	104.2	O2—C11—O1	123.6 (4)
C10—N1—C1	117.7 (4)	O2—C11—C12	117.7 (4)
C10—N1—Zn1	120.8 (3)	O1—C11—C12	118.6 (4)
C1—N1—Zn1	121.5 (3)	O3—C12—C13	111.7 (4)
C7—N2—C6	116.6 (4)	O3—C12—C11	107.6 (4)
N1—C1—C2	123.0 (4)	C13—C12—C11	111.0 (4)
N1—C1—H1	118.5	O3—C12—H4	108.8
C2—C1—H1	118.5	C13—C12—H4	108.8
C1—C2—C3	119.6 (4)	C11—C12—H4	108.8
C1—C2—H2	120.2	C12—C13—C14	115.3 (3)
C3—C2—H2	120.2	C12—C13—H13A	108.5
C9—C3—C2	117.2 (4)	C14—C13—H13A	108.5
C9—C3—C4	121.5 (4)	C12—C13—H13B	108.5
C2—C3—C4	121.2 (4)	C14—C13—H13B	108.5
C5—C4—C8	116.8 (4)	H13A—C13—H13B	107.5
C5—C4—C3	122.7 (4)	O5—C14—O4	121.4 (4)
C8—C4—C3	120.4 (4)	O5—C14—C13	118.8 (3)
C6—C5—C4	119.6 (5)	O4—C14—C13	119.8 (4)

Symmetry codes: (i) x, y, z−1; (ii) x+1/4, −y+1/4, z−3/4; (iii) x, y, z+1; (iv) x−1/4, −y+1/4, z+3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O2ⁱ	0.86	2.22	2.730 (6)	118
O2W—H14···O2	0.85	2.43	2.850 (6)	111
O3—H3···N2^v	0.84	2.13	2.721 (5)	127

Symmetry codes: (i) x, y, z−1; (v) −x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₄H₄O₅)(C₁₀H₈N₂)]·2H₂O
M_r	389.66
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	293
a, b, c (Å)	17.810 (5), 47.447 (9), 7.4063 (15)
V (Å³)	6259 (2)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.25 × 0.12 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.689, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	14679, 3380, 2817
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.087, 1.09
No. of reflections	3380
No. of parameters	217
No. of restraints	1
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0226P)² + 22.1041P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.37
Absolute structure	Flack (1983), 1438 Friedel pairs
Absolute structure parameter	0.006 (17)

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Selected bond lengths (Å) top

Zn1—N1	2.066 (3)	Zn1—O4ⁱ	2.031 (4)
Zn1—O1	1.985 (3)	Zn1—O5ⁱⁱ	1.999 (3)
Zn1—O3	2.188 (4)

Symmetry codes: (i) x, y, z−1; (ii) x+1/4, −y+1/4, z−3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O2ⁱ	0.86	2.22	2.730 (6)	117.9
O2W—H14···O2	0.85	2.43	2.850 (6)	111.2
O3—H3···N2ⁱⁱⁱ	0.84	2.13	2.721 (5)	126.6

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

Acknowledgements

This work was supported by the Natural Science Foundation of Shandong Province (ZR2011BQ004) and the Fundamental Research Funds for the Central Universities (09CX04045A).

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