Bis(μ-2,2′-oxydibenzoato-κ4O,O′:O′′,O′′′)bis­[(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)zinc(II)] dihydrate

Cui, H.; Li, W.-J.; Tao, R.-J.

doi:10.1107/S1600536808010271

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m697

doi:10.1107/S1600536808010271

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Bis(μ-2,2′-oxydibenzoato-κ⁴O,O′:O′′,O′′′)bis[(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)zinc(II)] dihydrate

Hong Cui,^a Wen-Juan Li ^b and Ruo-Jie Tao ^a ^*

^aInstitute of Molecular and Crystal Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China, and ^bDepartment of Civil and Environmental Engineering, East China Institute of Technology, 56 Xuefu Road, Fuzhou 344000, Jiangxi, People's Republic of China
^*Correspondence e-mail: zhw@henu.edu.cn

(Received 4 April 2008; accepted 15 April 2008; online 23 April 2008)

In the title compound, [Zn₂(C₁₄H₈O₅)₂(C₁₂H₁₂N₂)₂]·2H₂O, the Zn^II atom exhibits a distorted octahedral coordination geometry, defined by two N atoms from one 4,4′-dimethyl-2,2′-bipyridine ligand and four O atoms from two bridging 2,2′-oxydibenzoate ligands. The molecule is a centrosymmetric dimer. π–π Stacking interactions are observed between the 4,4′-dimethyl-2,2′-bipyridine ligands, with a centroid–centroid distance of 3.649 (2) Å.

Related literature

For related literature, see: Allen et al. (1987 ); Zhang et al. (2008 ).

Experimental

Crystal data

[Zn₂(C₁₄H₈O₅)₂(C₁₂H₁₂N₂)₂]·2H₂O
M_r = 1047.65
Triclinic, $[P \overline 1]$
a = 10.425 (2) Å
b = 10.866 (2) Å
c = 11.960 (2) Å
α = 68.413 (4)°
β = 66.721 (3)°
γ = 78.348 (4)°
V = 1154.7 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 293 (2) K
0.20 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.808, T_max = 0.851
6797 measured reflections
4484 independent reflections
3788 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.123
S = 1.16
4484 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O2	2.006 (3)
Zn1—O4ⁱ	2.053 (4)
Zn1—N2	2.059 (3)
Zn1—N1	2.086 (3)
Zn1—O5ⁱ	2.295 (5)
Zn1—O3	2.495 (4)

O2—Zn1—O4ⁱ	100.39 (14)
O2—Zn1—N2	100.84 (13)
O4ⁱ—Zn1—N2	96.86 (14)
O2—Zn1—N1	106.07 (12)
O4ⁱ—Zn1—N1	153.52 (14)
N2—Zn1—N1	79.25 (11)
O2—Zn1—O5ⁱ	145.16 (14)
O4ⁱ—Zn1—O5ⁱ	57.76 (14)
N2—Zn1—O5ⁱ	108.05 (15)
N1—Zn1—O5ⁱ	98.21 (12)
O2—Zn1—O3	56.84 (11)
O4ⁱ—Zn1—O3	99.09 (14)
N2—Zn1—O3	154.58 (12)
N1—Zn1—O3	94.60 (12)
O5ⁱ—Zn1—O3	97.20 (14)
Symmetry code: (i) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3	0.85	2.04	2.845 (5)	158
O1W—H1WB⋯O5ⁱ	0.85	2.07	2.876 (6)	158
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536808010271/hy2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010271/hy2127Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies (Zhang et al., 2008), we synthesized the title compound and report here its crystal structure.

The bond lengths and angles of the title compound are within normal ranges (Allen et al., 1987) (Table 1). Intermolecular hydrogen bonds are formed between the water molecule and the carboxylate groups (Fig. 1; Table 2). The molecule is centrosymmetric with an inversion center located at the midpoint of the Zn1 and Zn1ⁱ atoms [symmetry code (i): 1 - x, 2 - y, 1 - z]. The asymmetric unit thus contains one-half molecule. The Zn^II atom exhibits a distorted octahedral coordination geometry, defined by two N atoms from one 4,4'-dimethyl-2,2'-bipyridine (dbpy) ligand and four O atoms from two 2,2'-oxydibenzoate (odb) ligands. The two carboxylate groups of each odb ligand coordinate to two different Zn atoms.

The π–π stacking interactions between the aromatic rings of the dbpy ligands are observed, with a centroid–centroid distance of 3.649 (2)Å [Fig. 2; Cg1 = the centroid of N1ⁱⁱ, C15ⁱⁱ, C16ⁱⁱ, C17ⁱⁱ, C19ⁱⁱ, C20ⁱⁱ and Cg2 = the centroid of N2, C21, C22, C23, C25, C26; symmetry code: (ii) 2 - x, 2 - y, 1 - z].

Related literature top

For related literature, see: Allen et al. (1987); Zhang et al. (2008).

Experimental top

The title compound was synthesized hydrothermally in a Teflon-lined autoclave (23 ml) by heating a mixture of H₂odb (0.052 g, 0.2 mmol), dbpy (0.037 g, 0.2 mmol), Zn(NO₃)₂.6H₂O (0.059 g, 0.2 mmol) and one drop of Et₃N (pH = 8~9) in water (10 ml) at 393 K for 3 d. Colorless single crystals were collected in 56% yield based on Zn.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecular structure of the title compound. Displacement ellipsoids are drawn at the 20% probability level. Hydrogen bonds are indicated by dashed lines. [Symmetry code (i): 1 - x, 2 - y, 1 - z.]
	Fig. 2. A view of the crystal packing, showing the π–π stacking interaction.

Bis(µ-2,2'-oxydibenzoato- κ⁴O,O':O'',O''')βis[(4,4'-dimethyl-2,2'- bipyridine-κ²N,N')zinc(II)] dihydrate top

Crystal data top

[Zn₂(C₁₄H₈O₅)₂(C₁₂H₁₂N₂)₂]·2H₂O	Z = 1
M_r = 1047.65	F(000) = 540
Triclinic, P1	D_x = 1.507 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.425 (2) Å	Cell parameters from 2731 reflections
b = 10.866 (2) Å	θ = 2.3–27.8°
c = 11.960 (2) Å	µ = 1.11 mm⁻¹
α = 68.413 (4)°	T = 293 K
β = 66.721 (3)°	Block, colorless
γ = 78.348 (4)°	0.20 × 0.16 × 0.15 mm
V = 1154.7 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4484 independent reflections
Radiation source: fine-focus sealed tube	3788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.809, T_max = 0.851	k = −13→13
6797 measured reflections	l = −10→14

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0391P)² + 1.1151P] where P = (F_o² + 2F_c²)/3
4484 reflections	(Δ/σ)_max = 0.001
318 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³
0 constraints

Crystal data top

[Zn₂(C₁₄H₈O₅)₂(C₁₂H₁₂N₂)₂]·2H₂O	γ = 78.348 (4)°
M_r = 1047.65	V = 1154.7 (4) Å³
Triclinic, P1	Z = 1
a = 10.425 (2) Å	Mo Kα radiation
b = 10.866 (2) Å	µ = 1.11 mm⁻¹
c = 11.960 (2) Å	T = 293 K
α = 68.413 (4)°	0.20 × 0.16 × 0.15 mm
β = 66.721 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4484 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3788 reflections with I > 2σ(I)
T_min = 0.809, T_max = 0.851	R_int = 0.028
6797 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.16	Δρ_max = 0.79 e Å⁻³
4484 reflections	Δρ_min = −0.42 e Å⁻³
318 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.

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

	x	y	z	U_iso*/U_eq
Zn1	0.69886 (4)	0.81936 (4)	0.62615 (4)	0.02963 (15)
N1	0.8962 (3)	0.7397 (3)	0.6331 (3)	0.0290 (7)
N2	0.7562 (3)	0.9615 (3)	0.6702 (3)	0.0294 (7)
O1	0.7872 (3)	1.0671 (3)	0.1966 (3)	0.0402 (7)
O2	0.7264 (3)	0.9119 (3)	0.4398 (3)	0.0476 (7)
O3	0.7021 (4)	0.7032 (3)	0.4797 (3)	0.0653 (10)
O4	0.5135 (3)	1.1471 (4)	0.2926 (4)	0.0723 (11)
O5	0.4336 (4)	1.3253 (4)	0.1854 (5)	0.0931 (15)
O1W	0.6185 (5)	0.4727 (3)	0.6971 (4)	0.0904 (14)
H1WA	0.6406	0.5286	0.6219	0.109*
H1WB	0.6035	0.5144	0.7494	0.109*
C1	0.5330 (5)	1.2495 (5)	0.1998 (6)	0.0507 (12)
C2	0.6804 (4)	1.2853 (4)	0.1109 (4)	0.0366 (9)
C3	0.7046 (5)	1.4153 (4)	0.0292 (5)	0.0474 (11)
H3	0.6285	1.4758	0.0235	0.057*
C4	0.8373 (5)	1.4565 (4)	−0.0429 (5)	0.0522 (12)
H4	0.8506	1.5438	−0.0965	0.063*
C5	0.9501 (5)	1.3685 (5)	−0.0355 (4)	0.0497 (12)
H5	1.0402	1.3968	−0.0825	0.060*
C6	0.9309 (4)	1.2378 (4)	0.0413 (4)	0.0400 (10)
H6	1.0078	1.1776	0.0441	0.048*
C7	0.7965 (4)	1.1970 (4)	0.1141 (4)	0.0305 (8)
C8	0.7349 (4)	0.9736 (3)	0.1771 (4)	0.0311 (8)
C9	0.7182 (4)	0.9954 (4)	0.0613 (4)	0.0395 (10)
H9	0.7370	1.0770	−0.0029	0.047*
C10	0.6740 (5)	0.8971 (4)	0.0415 (4)	0.0469 (11)
H10	0.6611	0.9133	−0.0354	0.056*
C11	0.6487 (5)	0.7745 (4)	0.1344 (5)	0.0485 (11)
H11	0.6212	0.7071	0.1200	0.058*
C12	0.6650 (4)	0.7535 (4)	0.2488 (5)	0.0432 (10)
H12	0.6476	0.6707	0.3113	0.052*
C13	0.7062 (4)	0.8508 (4)	0.2750 (4)	0.0325 (8)
C14	0.7124 (4)	0.8198 (4)	0.4060 (4)	0.0401 (10)
C15	0.9622 (4)	0.6263 (3)	0.6140 (4)	0.0360 (9)
H15	0.9129	0.5688	0.6071	0.043*
C16	1.0999 (4)	0.5905 (4)	0.6042 (4)	0.0375 (9)
H16	1.1412	0.5100	0.5917	0.045*
C17	1.1763 (4)	0.6746 (4)	0.6130 (4)	0.0347 (9)
C18	1.3281 (5)	0.6431 (5)	0.5984 (6)	0.0558 (13)
H18A	1.3359	0.5799	0.6768	0.084*
H18B	1.3699	0.7228	0.5796	0.084*
H18C	1.3756	0.6065	0.5295	0.084*
C19	1.1067 (4)	0.7924 (3)	0.6351 (4)	0.0311 (8)
H19	1.1540	0.8513	0.6425	0.037*
C20	0.9681 (4)	0.8214 (3)	0.6458 (3)	0.0260 (8)
C21	0.8882 (4)	0.9448 (3)	0.6701 (3)	0.0258 (7)
C22	0.9417 (4)	1.0362 (3)	0.6920 (3)	0.0285 (8)
H22	1.0326	1.0222	0.6923	0.034*
C23	0.8611 (4)	1.1487 (3)	0.7136 (4)	0.0329 (9)
C24	0.9184 (5)	1.2489 (4)	0.7370 (5)	0.0450 (11)
H24A	0.9678	1.2041	0.7953	0.068*
H24B	0.8428	1.3055	0.7737	0.068*
H24C	0.9812	1.3013	0.6572	0.068*
C25	0.7257 (4)	1.1644 (4)	0.7143 (4)	0.0368 (9)
H25	0.6680	1.2384	0.7288	0.044*
C26	0.6775 (4)	1.0689 (4)	0.6931 (4)	0.0371 (9)
H26	0.5860	1.0798	0.6949	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0253 (2)	0.0322 (2)	0.0321 (3)	−0.00478 (16)	−0.00982 (19)	−0.01000 (19)
N1	0.0305 (17)	0.0258 (15)	0.0303 (17)	−0.0043 (12)	−0.0116 (15)	−0.0061 (13)
N2	0.0243 (16)	0.0322 (15)	0.0351 (18)	−0.0003 (12)	−0.0112 (14)	−0.0144 (14)
O1	0.0490 (18)	0.0403 (15)	0.0358 (16)	−0.0131 (13)	−0.0210 (14)	−0.0053 (13)
O2	0.0485 (19)	0.0604 (19)	0.0336 (16)	−0.0092 (15)	−0.0156 (15)	−0.0106 (15)
O3	0.076 (2)	0.0526 (19)	0.053 (2)	−0.0105 (17)	−0.033 (2)	0.0133 (17)
O4	0.040 (2)	0.113 (3)	0.051 (2)	−0.034 (2)	−0.0021 (17)	−0.013 (2)
O5	0.040 (2)	0.069 (2)	0.155 (5)	0.0009 (18)	−0.023 (3)	−0.034 (3)
O1W	0.115 (4)	0.0360 (18)	0.091 (3)	0.000 (2)	−0.016 (3)	−0.014 (2)
C1	0.033 (3)	0.051 (3)	0.078 (4)	−0.005 (2)	−0.013 (3)	−0.038 (3)
C2	0.031 (2)	0.042 (2)	0.039 (2)	−0.0068 (17)	−0.0070 (19)	−0.0184 (19)
C3	0.051 (3)	0.038 (2)	0.053 (3)	−0.0012 (19)	−0.019 (2)	−0.015 (2)
C4	0.073 (4)	0.037 (2)	0.042 (3)	−0.021 (2)	−0.014 (3)	−0.006 (2)
C5	0.048 (3)	0.061 (3)	0.038 (2)	−0.032 (2)	−0.001 (2)	−0.015 (2)
C6	0.030 (2)	0.051 (2)	0.039 (2)	−0.0054 (18)	−0.0098 (19)	−0.016 (2)
C7	0.034 (2)	0.0351 (19)	0.0239 (19)	−0.0122 (16)	−0.0099 (17)	−0.0072 (16)
C8	0.0245 (19)	0.0331 (19)	0.035 (2)	−0.0020 (15)	−0.0083 (17)	−0.0120 (17)
C9	0.047 (3)	0.042 (2)	0.027 (2)	−0.0101 (19)	−0.012 (2)	−0.0077 (18)
C10	0.052 (3)	0.057 (3)	0.041 (3)	−0.004 (2)	−0.017 (2)	−0.025 (2)
C11	0.051 (3)	0.042 (2)	0.060 (3)	−0.003 (2)	−0.019 (2)	−0.026 (2)
C12	0.035 (2)	0.034 (2)	0.053 (3)	0.0008 (17)	−0.011 (2)	−0.012 (2)
C13	0.027 (2)	0.0325 (19)	0.034 (2)	0.0011 (15)	−0.0090 (18)	−0.0096 (17)
C14	0.024 (2)	0.050 (2)	0.034 (2)	−0.0015 (17)	−0.0089 (18)	−0.002 (2)
C15	0.043 (2)	0.0257 (18)	0.040 (2)	−0.0070 (16)	−0.015 (2)	−0.0086 (17)
C16	0.043 (2)	0.0263 (18)	0.042 (2)	0.0070 (16)	−0.016 (2)	−0.0138 (18)
C17	0.033 (2)	0.036 (2)	0.035 (2)	0.0031 (16)	−0.0127 (18)	−0.0122 (18)
C18	0.039 (3)	0.055 (3)	0.085 (4)	0.018 (2)	−0.031 (3)	−0.036 (3)
C19	0.032 (2)	0.0329 (19)	0.032 (2)	0.0001 (15)	−0.0148 (18)	−0.0115 (17)
C20	0.0282 (19)	0.0241 (16)	0.0236 (18)	−0.0021 (14)	−0.0077 (16)	−0.0068 (15)
C21	0.0258 (19)	0.0260 (17)	0.0230 (18)	−0.0020 (14)	−0.0065 (16)	−0.0071 (15)
C22	0.028 (2)	0.0301 (18)	0.0272 (19)	−0.0025 (15)	−0.0100 (17)	−0.0080 (16)
C23	0.039 (2)	0.0294 (18)	0.029 (2)	−0.0051 (16)	−0.0103 (18)	−0.0085 (17)
C24	0.052 (3)	0.038 (2)	0.053 (3)	−0.0059 (19)	−0.017 (2)	−0.023 (2)
C25	0.035 (2)	0.0309 (19)	0.044 (2)	0.0037 (16)	−0.013 (2)	−0.0149 (19)
C26	0.027 (2)	0.034 (2)	0.051 (3)	0.0043 (16)	−0.014 (2)	−0.0168 (19)

Geometric parameters (Å, º) top

Zn1—O2	2.006 (3)	C8—C13	1.405 (5)
Zn1—O4ⁱ	2.053 (4)	C9—C10	1.370 (6)
Zn1—N2	2.059 (3)	C9—H9	0.9300
Zn1—N1	2.086 (3)	C10—C11	1.379 (6)
Zn1—O5ⁱ	2.295 (5)	C10—H10	0.9300
Zn1—O3	2.495 (4)	C11—C12	1.375 (6)
N1—C15	1.335 (5)	C11—H11	0.9300
N1—C20	1.353 (4)	C12—C13	1.391 (5)
N2—C26	1.335 (5)	C12—H12	0.9300
N2—C21	1.350 (4)	C13—C14	1.501 (6)
O1—C8	1.372 (4)	C15—C16	1.378 (5)
O1—C7	1.389 (4)	C15—H15	0.9300
O2—C14	1.261 (5)	C16—C17	1.383 (5)
O3—C14	1.246 (5)	C16—H16	0.9300
O4—C1	1.231 (6)	C17—C19	1.399 (5)
O4—Zn1ⁱ	2.053 (4)	C17—C18	1.503 (5)
O5—C1	1.214 (5)	C18—H18A	0.9600
O5—Zn1ⁱ	2.295 (5)	C18—H18B	0.9600
O1W—H1WA	0.8500	C18—H18C	0.9600
O1W—H1WB	0.8500	C19—C20	1.380 (5)
C1—C2	1.512 (6)	C19—H19	0.9300
C1—Zn1ⁱ	2.519 (5)	C20—C21	1.489 (5)
C2—C7	1.389 (5)	C21—C22	1.378 (5)
C2—C3	1.395 (6)	C22—C23	1.383 (5)
C3—C4	1.372 (6)	C22—H22	0.9300
C3—H3	0.9300	C23—C25	1.385 (5)
C4—C5	1.367 (7)	C23—C24	1.497 (5)
C4—H4	0.9300	C24—H24A	0.9600
C5—C6	1.382 (6)	C24—H24B	0.9600
C5—H5	0.9300	C24—H24C	0.9600
C6—C7	1.386 (5)	C25—C26	1.377 (5)
C6—H6	0.9300	C25—H25	0.9300
C8—C9	1.392 (5)	C26—H26	0.9300

O2—Zn1—O4ⁱ	100.39 (14)	C10—C9—C8	120.3 (4)
O2—Zn1—N2	100.84 (13)	C10—C9—H9	119.8
O4ⁱ—Zn1—N2	96.86 (14)	C8—C9—H9	119.8
O2—Zn1—N1	106.07 (12)	C9—C10—C11	120.7 (4)
O4ⁱ—Zn1—N1	153.52 (14)	C9—C10—H10	119.7
N2—Zn1—N1	79.25 (11)	C11—C10—H10	119.7
O2—Zn1—O5ⁱ	145.16 (14)	C12—C11—C10	118.8 (4)
O4ⁱ—Zn1—O5ⁱ	57.76 (14)	C12—C11—H11	120.6
N2—Zn1—O5ⁱ	108.05 (15)	C10—C11—H11	120.6
N1—Zn1—O5ⁱ	98.21 (12)	C11—C12—C13	122.8 (4)
O2—Zn1—O3	56.84 (11)	C11—C12—H12	118.6
O4ⁱ—Zn1—O3	99.09 (14)	C13—C12—H12	118.6
N2—Zn1—O3	154.58 (12)	C12—C13—C8	117.0 (4)
N1—Zn1—O3	94.60 (12)	C12—C13—C14	118.4 (4)
O5ⁱ—Zn1—O3	97.20 (14)	C8—C13—C14	124.6 (4)
O2—Zn1—C1ⁱ	124.65 (15)	O3—C14—O2	121.3 (4)
O4ⁱ—Zn1—C1ⁱ	29.03 (14)	O3—C14—C13	119.1 (4)
N2—Zn1—C1ⁱ	104.76 (13)	O2—C14—C13	119.6 (3)
N1—Zn1—C1ⁱ	126.34 (15)	N1—C15—C16	123.2 (3)
O5ⁱ—Zn1—C1ⁱ	28.74 (14)	N1—C15—H15	118.4
O3—Zn1—C1ⁱ	98.76 (13)	C16—C15—H15	118.4
C15—N1—C20	117.9 (3)	C15—C16—C17	119.7 (3)
C15—N1—Zn1	127.7 (2)	C15—C16—H16	120.1
C20—N1—Zn1	114.0 (2)	C17—C16—H16	120.1
C26—N2—C21	118.4 (3)	C16—C17—C19	117.2 (3)
C26—N2—Zn1	126.0 (2)	C16—C17—C18	122.2 (4)
C21—N2—Zn1	115.5 (2)	C19—C17—C18	120.7 (4)
C8—O1—C7	121.0 (3)	C17—C18—H18A	109.5
C14—O2—Zn1	101.8 (3)	C17—C18—H18B	109.5
C14—O3—Zn1	79.6 (3)	H18A—C18—H18B	109.5
C1—O4—Zn1ⁱ	97.0 (3)	C17—C18—H18C	109.5
C1—O5—Zn1ⁱ	85.9 (4)	H18A—C18—H18C	109.5
H1WA—O1W—H1WB	107.7	H18B—C18—H18C	109.5
O5—C1—O4	119.3 (5)	C20—C19—C17	120.1 (3)
O5—C1—C2	120.5 (5)	C20—C19—H19	119.9
O4—C1—C2	120.1 (4)	C17—C19—H19	119.9
O5—C1—Zn1ⁱ	65.3 (3)	N1—C20—C19	121.8 (3)
O4—C1—Zn1ⁱ	54.0 (3)	N1—C20—C21	115.6 (3)
C2—C1—Zn1ⁱ	171.7 (4)	C19—C20—C21	122.7 (3)
C7—C2—C3	117.3 (4)	N2—C21—C22	121.3 (3)
C7—C2—C1	122.8 (4)	N2—C21—C20	115.0 (3)
C3—C2—C1	119.6 (4)	C22—C21—C20	123.7 (3)
C4—C3—C2	122.0 (4)	C21—C22—C23	120.4 (3)
C4—C3—H3	119.0	C21—C22—H22	119.8
C2—C3—H3	119.0	C23—C22—H22	119.8
C5—C4—C3	119.6 (4)	C22—C23—C25	117.8 (3)
C5—C4—H4	120.2	C22—C23—C24	120.9 (3)
C3—C4—H4	120.2	C25—C23—C24	121.4 (4)
C4—C5—C6	120.4 (4)	C23—C24—H24A	109.5
C4—C5—H5	119.8	C23—C24—H24B	109.5
C6—C5—H5	119.8	H24A—C24—H24B	109.5
C5—C6—C7	119.6 (4)	C23—C24—H24C	109.5
C5—C6—H6	120.2	H24A—C24—H24C	109.5
C7—C6—H6	120.2	H24B—C24—H24C	109.5
C6—C7—O1	115.8 (3)	C26—C25—C23	119.2 (4)
C6—C7—C2	121.0 (4)	C26—C25—H25	120.4
O1—C7—C2	123.0 (3)	C23—C25—H25	120.4
O1—C8—C9	121.5 (3)	N2—C26—C25	122.9 (3)
O1—C8—C13	118.0 (3)	N2—C26—H26	118.5
C9—C8—C13	120.3 (3)	C25—C26—H26	118.5

O2—Zn1—N1—C15	−82.0 (3)	C1—C2—C7—C6	−172.7 (4)
O4ⁱ—Zn1—N1—C15	95.9 (4)	C3—C2—C7—O1	176.2 (3)
N2—Zn1—N1—C15	179.7 (3)	C1—C2—C7—O1	1.9 (6)
O5ⁱ—Zn1—N1—C15	72.7 (3)	C7—O1—C8—C9	14.3 (6)
O3—Zn1—N1—C15	−25.3 (3)	C7—O1—C8—C13	−169.4 (3)
C1ⁱ—Zn1—N1—C15	79.1 (4)	O1—C8—C9—C10	175.9 (4)
O2—Zn1—N1—C20	90.9 (3)	C13—C8—C9—C10	−0.3 (6)
O4ⁱ—Zn1—N1—C20	−91.2 (4)	C8—C9—C10—C11	−1.5 (7)
N2—Zn1—N1—C20	−7.4 (2)	C9—C10—C11—C12	1.7 (7)
O5ⁱ—Zn1—N1—C20	−114.4 (3)	C10—C11—C12—C13	−0.1 (7)
O3—Zn1—N1—C20	147.7 (3)	C11—C12—C13—C8	−1.6 (6)
C1ⁱ—Zn1—N1—C20	−107.9 (3)	C11—C12—C13—C14	176.4 (4)
O2—Zn1—N2—C26	78.6 (3)	O1—C8—C13—C12	−174.5 (3)
O4ⁱ—Zn1—N2—C26	−23.5 (4)	C9—C8—C13—C12	1.8 (6)
N1—Zn1—N2—C26	−176.9 (3)	O1—C8—C13—C14	7.6 (6)
O5ⁱ—Zn1—N2—C26	−81.7 (3)	C9—C8—C13—C14	−176.1 (4)
O3—Zn1—N2—C26	105.1 (4)	Zn1—O3—C14—O2	6.0 (4)
C1ⁱ—Zn1—N2—C26	−51.9 (4)	Zn1—O3—C14—C13	−173.3 (3)
O2—Zn1—N2—C21	−98.6 (3)	Zn1—O2—C14—O3	−7.5 (5)
O4ⁱ—Zn1—N2—C21	159.4 (3)	Zn1—O2—C14—C13	171.8 (3)
N1—Zn1—N2—C21	5.9 (3)	C12—C13—C14—O3	11.0 (6)
O5ⁱ—Zn1—N2—C21	101.1 (3)	C8—C13—C14—O3	−171.1 (4)
O3—Zn1—N2—C21	−72.0 (4)	C12—C13—C14—O2	−168.3 (4)
C1ⁱ—Zn1—N2—C21	130.9 (3)	C8—C13—C14—O2	9.6 (6)
O4ⁱ—Zn1—O2—C14	−90.3 (3)	C20—N1—C15—C16	−1.4 (6)
N2—Zn1—O2—C14	170.5 (2)	Zn1—N1—C15—C16	171.3 (3)
N1—Zn1—O2—C14	88.7 (3)	N1—C15—C16—C17	−0.6 (6)
O5ⁱ—Zn1—O2—C14	−43.6 (4)	C15—C16—C17—C19	1.6 (6)
O3—Zn1—O2—C14	3.8 (2)	C15—C16—C17—C18	−177.8 (4)
C1ⁱ—Zn1—O2—C14	−72.9 (3)	C16—C17—C19—C20	−0.7 (6)
O2—Zn1—O3—C14	−3.8 (2)	C18—C17—C19—C20	178.8 (4)
O4ⁱ—Zn1—O3—C14	92.7 (3)	C15—N1—C20—C19	2.4 (5)
N2—Zn1—O3—C14	−35.5 (4)	Zn1—N1—C20—C19	−171.3 (3)
N1—Zn1—O3—C14	−110.0 (2)	C15—N1—C20—C21	−178.6 (3)
O5ⁱ—Zn1—O3—C14	151.1 (2)	Zn1—N1—C20—C21	7.8 (4)
C1ⁱ—Zn1—O3—C14	122.1 (3)	C17—C19—C20—N1	−1.4 (6)
Zn1ⁱ—O5—C1—O4	1.9 (5)	C17—C19—C20—C21	179.6 (3)
Zn1ⁱ—O5—C1—C2	−173.3 (4)	C26—N2—C21—C22	−0.5 (5)
Zn1ⁱ—O4—C1—O5	−2.1 (5)	Zn1—N2—C21—C22	176.9 (3)
Zn1ⁱ—O4—C1—C2	173.1 (3)	C26—N2—C21—C20	179.0 (3)
O5—C1—C2—C7	−172.9 (5)	Zn1—N2—C21—C20	−3.6 (4)
O4—C1—C2—C7	12.0 (7)	N1—C20—C21—N2	−2.9 (5)
O5—C1—C2—C3	12.9 (7)	C19—C20—C21—N2	176.2 (3)
O4—C1—C2—C3	−162.2 (4)	N1—C20—C21—C22	176.6 (3)
C7—C2—C3—C4	−1.7 (7)	C19—C20—C21—C22	−4.3 (6)
C1—C2—C3—C4	172.8 (4)	N2—C21—C22—C23	−0.6 (6)
C2—C3—C4—C5	0.1 (7)	C20—C21—C22—C23	179.9 (3)
C3—C4—C5—C6	1.8 (7)	C21—C22—C23—C25	1.0 (6)
C4—C5—C6—C7	−1.9 (7)	C21—C22—C23—C24	−179.8 (4)
C5—C6—C7—O1	−174.8 (4)	C22—C23—C25—C26	−0.3 (6)
C5—C6—C7—C2	0.2 (6)	C24—C23—C25—C26	−179.5 (4)
C8—O1—C7—C6	−113.1 (4)	C21—N2—C26—C25	1.2 (6)
C8—O1—C7—C2	72.0 (5)	Zn1—N2—C26—C25	−175.9 (3)
C3—C2—C7—C6	1.6 (6)	C23—C25—C26—N2	−0.8 (6)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.85	2.04	2.845 (5)	158
O1W—H1WB···O5ⁱ	0.85	2.07	2.876 (6)	158

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₁₄H₈O₅)₂(C₁₂H₁₂N₂)₂]·2H₂O
M_r	1047.65
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.425 (2), 10.866 (2), 11.960 (2)
α, β, γ (°)	68.413 (4), 66.721 (3), 78.348 (4)
V (Å³)	1154.7 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.809, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	6797, 4484, 3788
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.123, 1.16
No. of reflections	4484
No. of parameters	318
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.42

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—O2	2.006 (3)	Zn1—N1	2.086 (3)
Zn1—O4ⁱ	2.053 (4)	Zn1—O5ⁱ	2.295 (5)
Zn1—N2	2.059 (3)	Zn1—O3	2.495 (4)

O2—Zn1—O4ⁱ	100.39 (14)	N2—Zn1—O5ⁱ	108.05 (15)
O2—Zn1—N2	100.84 (13)	N1—Zn1—O5ⁱ	98.21 (12)
O4ⁱ—Zn1—N2	96.86 (14)	O2—Zn1—O3	56.84 (11)
O2—Zn1—N1	106.07 (12)	O4ⁱ—Zn1—O3	99.09 (14)
O4ⁱ—Zn1—N1	153.52 (14)	N2—Zn1—O3	154.58 (12)
N2—Zn1—N1	79.25 (11)	N1—Zn1—O3	94.60 (12)
O2—Zn1—O5ⁱ	145.16 (14)	O5ⁱ—Zn1—O3	97.20 (14)
O4ⁱ—Zn1—O5ⁱ	57.76 (14)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.85	2.04	2.845 (5)	158
O1W—H1WB···O5ⁱ	0.85	2.07	2.876 (6)	158

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

The authors are grateful for financial support provided by the Henan Administration of Science and Technology (grant No. 0111030700).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, W., Yao, L. & Tao, R. (2008). Acta Cryst. E64, m169. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 5| May 2008| Page m697

doi:10.1107/S1600536808010271

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