(5,5′-Dicarboxy­biphenyl-2,2′-dicarboxyl­ato-κ2O2,O2′)bis­(1,10-phenanthroline-κ2N,N′)zinc(II) dihydrate

Chen, R.-Z.; Guo, F.-J.; Meng, F.-L.

doi:10.1107/S1600536808015742

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m855

doi:10.1107/S1600536808015742

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(5,5′-Dicarboxybiphenyl-2,2′-dicarboxylato-κ²O²,O^2′)bis(1,10-phenanthroline-κ²N,N′)zinc(II) dihydrate

Rui-Zhan Chen,^a,^b ^* Fei-Jun Guo ^a and Fan-Lei Meng ^a

^aCollege of Chemistry, Changchun Normal University, Changchun 130032, People's Republic of China, and ^bChangchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun Center of Mass Spectrometry, Changchun 130022, People's Republic of China
^*Correspondence e-mail: rzchenchem@yahoo.cn

(Received 5 May 2008; accepted 26 May 2008; online 7 June 2008)

In the title compound, [Zn(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O, the Zn^II atom is located on a twofold rotation axis and is six-coordinated by two O atoms from a 5,5′-dicarboxybiphenyl-2,2′-dicarboxylate ligand and four N atoms from two 1,10-phenanthroline molecules in a distorted octahedral geometry. The crystal structure involves O—H⋯O hydrogen bonds.

Related literature

For related literature, see: Che et al. (2006 ); Chen et al. (2008 ); Lehn (1990 ); Zang et al. (2006 ).

Experimental

Crystal data

[Zn(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O
M_r = 790.03
Monoclinic, C 2/c
a = 16.901 (5) Å
b = 9.473 (3) Å
c = 22.126 (7) Å
β = 96.429 (5)°
V = 3520.4 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 293 (2) K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.817, T_max = 0.853
9664 measured reflections
3487 independent reflections
2437 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.124
S = 1.04
3487 reflections
255 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	2.102 (2)
Zn1—N1	2.130 (3)
Zn1—N2	2.199 (3)

O1—Zn1—O1ⁱ	106.16 (11)
O1—Zn1—N1ⁱ	98.70 (10)
O1—Zn1—N1	87.72 (10)
N1ⁱ—Zn1—N1	169.36 (16)
O1—Zn1—N2	162.88 (11)
N1—Zn1—N2	76.44 (13)
O1—Zn1—N2ⁱ	82.94 (10)
N1—Zn1—N2ⁱ	96.08 (12)
N2—Zn1—N2ⁱ	92.23 (15)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱⁱ	0.82	1.74	2.538 (3)	162
O1W—H1B⋯O4ⁱⁱⁱ	0.86 (3)	2.24 (2)	2.966 (4)	143 (3)
O1W—H1A⋯O2	0.85 (3)	2.00 (2)	2.808 (4)	159 (4)
Symmetry codes: (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) -x+1, -y, -z+2.

Data collection: SMART (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 global, I. DOI: 10.1107/S1600536808015742/hy2133sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015742/hy2133Isup2.hkl

checkCIF report

Comment top

In the construction of new coordination polymers, multi-carboxylates act as multifunctional organic ligands not only due to their various coordination modes, resulting from fully or partially deprotonated sites, to allow for the large diversity in topologies, but also due to the ability to act as hydrogen-bond acceptors and donors to assemble supramolecular structures (Che et al., 2006; Chen et al., 2008; Lehn, 1990). We chose biphenyl-2,5,2',5'-tetracarboxylic acid (H₄bptc) as a bridging ligand, 1,10-phenanthroline (phen) as a neutral ligand, and zinc(II) as a metal center, generating the title compound. We report here its crystal structure.

In the title compound, the Zn^II atom, lying on a twofold rotation axis, is six-coordinated by two O atoms from one H₂bptc ligand and four N atoms from two phen molecules in a distorted octahedral geometry (Fig. 1). The twofold rotation axis passes through the midpoint of the bond connecting two benzene rings of the H₂bptc ligand. The bond lengths are within the normal ranges (Table 1) (Zang et al., 2006). The crystal structure involves O—H···O hydrogen bonds between the carboxylate O atoms and water molecules (Table 2).

Related literature top

For related literature, see: Che et al. (2006); Chen et al. (2008); Lehn (1990); Zang et al. (2006).

Experimental top

A mixture of ZnCl₂.2H₂O (0.017 g, 0.1 mmol), H₄bptc (0.066 g, 0.2 mmol), phen (0.040 g, 0.2 mmol) and H₂O(15 ml) in a 25 ml Teflon-lined stainless steel reactor was heated from 298 to 443 K in 2 h and a constant temperature was maintained at 443 K for 72 h. After cooling to 298 K, colorless crystals of the title compound were obtained from the reaction.

Computing details top

Data collection: SMART (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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) 1-x, y, 1.5-z.]

(5,5'-Dicarboxybiphenyl-2,2'-dicarboxylato-κ²O²,O^2')bis(1,10- phenanthroline-κ²N,N')zinc(II) dihydrate top

Crystal data top

[Zn(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O	F(000) = 1624
M_r = 790.03	D_x = 1.491 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3487 reflections
a = 16.901 (5) Å	θ = 2.0–26.0°
b = 9.473 (3) Å	µ = 0.77 mm⁻¹
c = 22.126 (7) Å	T = 293 K
β = 96.429 (5)°	Block, colorless
V = 3520.4 (19) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 26.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→18
T_min = 0.817, T_max = 0.853	k = −11→11
9664 measured reflections	l = −21→27

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) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0505P)² + 0.8309P] where P = (F_o² + 2F_c²)/3
3487 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Zn(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O	V = 3520.4 (19) Å³
M_r = 790.03	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 16.901 (5) Å	µ = 0.77 mm⁻¹
b = 9.473 (3) Å	T = 293 K
c = 22.126 (7) Å	0.26 × 0.22 × 0.20 mm
β = 96.429 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3487 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2437 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.853	R_int = 0.049
9664 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	2 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
3487 reflections	Δρ_min = −0.22 e Å⁻³
255 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
C1	0.3739 (2)	0.3651 (5)	0.63923 (18)	0.0637 (11)
H1	0.3543	0.2958	0.6634	0.076*
C2	0.3354 (3)	0.3873 (6)	0.5804 (2)	0.0880 (16)
H2	0.2913	0.3337	0.5656	0.106*
C3	0.3645 (3)	0.4896 (6)	0.5454 (2)	0.0926 (17)
H3	0.3390	0.5077	0.5067	0.111*
C4	0.4311 (3)	0.5664 (5)	0.5667 (2)	0.0762 (14)
C5	0.4663 (4)	0.6727 (6)	0.5317 (2)	0.0988 (19)
H5	0.4424	0.6948	0.4929	0.119*
C6	0.5326 (4)	0.7401 (6)	0.5538 (3)	0.106 (2)
H6	0.5542	0.8074	0.5298	0.127*
C7	0.5713 (3)	0.7116 (4)	0.6134 (2)	0.0776 (14)
C8	0.6414 (4)	0.7740 (5)	0.6377 (3)	0.098 (2)
H8	0.6659	0.8408	0.6152	0.117*
C9	0.6744 (3)	0.7386 (5)	0.6936 (3)	0.0906 (17)
H9	0.7222	0.7793	0.7098	0.109*
C10	0.6361 (3)	0.6400 (4)	0.7274 (2)	0.0722 (13)
H10	0.6593	0.6164	0.7661	0.087*
C11	0.5368 (3)	0.6116 (4)	0.6493 (2)	0.0600 (11)
C12	0.4662 (3)	0.5378 (4)	0.62567 (18)	0.0588 (11)
C13	0.40756 (18)	0.1983 (3)	0.81456 (14)	0.0328 (7)
C14	0.47901 (16)	0.1060 (3)	0.82887 (12)	0.0264 (7)
C15	0.51756 (16)	0.0460 (3)	0.78249 (12)	0.0240 (6)
C16	0.58975 (17)	−0.0230 (3)	0.79802 (13)	0.0299 (7)
H16	0.6169	−0.0613	0.7676	0.036*
C17	0.62178 (18)	−0.0353 (3)	0.85843 (14)	0.0335 (7)
C18	0.58141 (19)	0.0192 (4)	0.90393 (14)	0.0421 (9)
H18	0.6021	0.0094	0.9445	0.051*
C19	0.51007 (18)	0.0882 (3)	0.88893 (13)	0.0383 (8)
H19	0.4824	0.1235	0.9197	0.046*
C20	0.6999 (2)	−0.1096 (4)	0.87475 (16)	0.0460 (9)
N1	0.43688 (18)	0.4390 (3)	0.66158 (13)	0.0510 (8)
N2	0.5682 (2)	0.5791 (3)	0.70633 (15)	0.0563 (8)
O1	0.40798 (12)	0.2849 (2)	0.77191 (9)	0.0370 (5)
O2	0.35134 (14)	0.1861 (3)	0.84667 (11)	0.0646 (8)
O1W	0.33466 (18)	0.0544 (3)	0.95823 (12)	0.0704 (8)
O3	0.73266 (15)	−0.1494 (3)	0.82746 (11)	0.0707 (9)
H3A	0.7749	−0.1893	0.8384	0.106*
O4	0.72855 (15)	−0.1289 (3)	0.92612 (11)	0.0786 (10)
Zn1	0.5000	0.41820 (6)	0.7500	0.0430 (2)
H1B	0.315 (2)	0.112 (3)	0.9823 (14)	0.064*
H1A	0.333 (2)	0.110 (3)	0.9282 (12)	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (3)	0.081 (3)	0.058 (3)	0.011 (2)	0.009 (2)	0.017 (2)
C2	0.054 (3)	0.135 (5)	0.074 (3)	0.021 (3)	0.002 (2)	0.021 (3)
C3	0.085 (4)	0.133 (5)	0.061 (3)	0.046 (4)	0.016 (3)	0.038 (3)
C4	0.092 (4)	0.076 (3)	0.065 (3)	0.033 (3)	0.030 (3)	0.029 (3)
C5	0.145 (6)	0.088 (4)	0.072 (4)	0.041 (4)	0.049 (4)	0.042 (3)
C6	0.168 (6)	0.065 (4)	0.097 (5)	0.018 (4)	0.071 (4)	0.030 (3)
C7	0.116 (4)	0.045 (3)	0.084 (4)	0.007 (3)	0.065 (3)	0.006 (2)
C8	0.151 (6)	0.051 (3)	0.109 (5)	−0.032 (3)	0.093 (4)	−0.018 (3)
C9	0.113 (4)	0.068 (3)	0.104 (4)	−0.040 (3)	0.071 (4)	−0.032 (3)
C10	0.093 (4)	0.052 (2)	0.081 (3)	−0.023 (2)	0.047 (3)	−0.020 (2)
C11	0.083 (3)	0.035 (2)	0.070 (3)	0.007 (2)	0.044 (2)	−0.0001 (19)
C12	0.076 (3)	0.051 (2)	0.056 (3)	0.027 (2)	0.033 (2)	0.0180 (19)
C13	0.0281 (18)	0.0396 (18)	0.0312 (18)	0.0106 (14)	0.0054 (14)	0.0015 (15)
C14	0.0225 (16)	0.0314 (17)	0.0255 (16)	0.0040 (12)	0.0037 (12)	−0.0001 (12)
C15	0.0231 (16)	0.0238 (15)	0.0253 (16)	0.0002 (11)	0.0036 (12)	0.0000 (11)
C16	0.0247 (17)	0.0352 (17)	0.0304 (18)	0.0077 (13)	0.0056 (13)	−0.0018 (13)
C17	0.0262 (18)	0.0431 (18)	0.0310 (18)	0.0093 (14)	0.0018 (13)	0.0017 (14)
C18	0.039 (2)	0.063 (2)	0.0236 (18)	0.0165 (17)	0.0000 (14)	−0.0008 (16)
C19	0.0358 (19)	0.054 (2)	0.0266 (17)	0.0185 (16)	0.0097 (14)	−0.0025 (15)
C20	0.033 (2)	0.070 (3)	0.035 (2)	0.0191 (17)	0.0034 (16)	0.0049 (17)
N1	0.051 (2)	0.0519 (19)	0.052 (2)	0.0120 (16)	0.0165 (15)	0.0146 (15)
N2	0.072 (2)	0.0382 (17)	0.066 (2)	−0.0056 (17)	0.0362 (18)	−0.0067 (16)
O1	0.0319 (13)	0.0374 (12)	0.0422 (13)	0.0101 (10)	0.0063 (10)	0.0116 (10)
O2	0.0449 (16)	0.098 (2)	0.0564 (17)	0.0427 (15)	0.0294 (12)	0.0411 (15)
O1W	0.079 (2)	0.088 (2)	0.0457 (19)	0.0195 (17)	0.0126 (15)	0.0143 (15)
O3	0.0530 (17)	0.121 (2)	0.0388 (15)	0.0559 (17)	0.0072 (12)	0.0098 (15)
O4	0.0610 (19)	0.133 (3)	0.0394 (16)	0.0561 (18)	−0.0040 (13)	0.0029 (16)
Zn1	0.0470 (4)	0.0373 (3)	0.0467 (4)	0.000	0.0144 (3)	0.000

Geometric parameters (Å, º) top

C1—N1	1.323 (5)	C13—O2	1.254 (4)
C1—C2	1.405 (6)	C13—C14	1.496 (4)
C1—H1	0.9300	C14—C19	1.383 (4)
C2—C3	1.366 (7)	C14—C15	1.396 (4)
C2—H2	0.9300	C15—C16	1.393 (4)
C3—C4	1.378 (7)	C15—C15ⁱ	1.493 (5)
C3—H3	0.9300	C16—C17	1.390 (4)
C4—C12	1.399 (6)	C16—H16	0.9300
C4—C5	1.439 (7)	C17—C18	1.378 (4)
C5—C6	1.334 (7)	C17—C20	1.504 (4)
C5—H5	0.9300	C18—C19	1.379 (4)
C6—C7	1.431 (7)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.378 (7)	C20—O4	1.198 (4)
C7—C11	1.404 (5)	C20—O3	1.294 (4)
C8—C9	1.341 (7)	N1—Zn1	2.130 (3)
C8—H8	0.9300	N2—Zn1	2.199 (3)
C9—C10	1.399 (6)	O1—Zn1	2.102 (2)
C9—H9	0.9300	O1W—H1B	0.86 (3)
C10—N2	1.321 (5)	O1W—H1A	0.85 (3)
C10—H10	0.9300	O3—H3A	0.8200
C11—N2	1.348 (5)	Zn1—O1	2.102 (2)
C11—C12	1.431 (6)	Zn1—N1	2.130 (3)
C12—N1	1.357 (4)	Zn1—N2	2.199 (3)
C13—O1	1.251 (3)

N1—C1—C2	122.5 (4)	C16—C15—C14	118.5 (3)
N1—C1—H1	118.8	C16—C15—C15ⁱ	118.7 (3)
C2—C1—H1	118.8	C14—C15—C15ⁱ	122.7 (3)
C3—C2—C1	118.2 (5)	C17—C16—C15	120.9 (3)
C3—C2—H2	120.9	C17—C16—H16	119.6
C1—C2—H2	120.9	C15—C16—H16	119.6
C2—C3—C4	120.8 (5)	C18—C17—C16	120.0 (3)
C2—C3—H3	119.6	C18—C17—C20	119.5 (3)
C4—C3—H3	119.6	C16—C17—C20	120.5 (3)
C3—C4—C12	117.5 (4)	C17—C18—C19	119.5 (3)
C3—C4—C5	123.8 (5)	C17—C18—H18	120.2
C12—C4—C5	118.7 (5)	C19—C18—H18	120.2
C6—C5—C4	121.3 (5)	C18—C19—C14	121.1 (3)
C6—C5—H5	119.4	C18—C19—H19	119.5
C4—C5—H5	119.4	C14—C19—H19	119.5
C5—C6—C7	121.7 (5)	O4—C20—O3	124.0 (3)
C5—C6—H6	119.1	O4—C20—C17	123.3 (3)
C7—C6—H6	119.1	O3—C20—C17	112.7 (3)
C8—C7—C11	117.4 (5)	C1—N1—C12	118.5 (4)
C8—C7—C6	124.2 (5)	C1—N1—Zn1	126.4 (3)
C11—C7—C6	118.3 (5)	C12—N1—Zn1	115.1 (3)
C9—C8—C7	120.2 (5)	C10—N2—C11	117.7 (4)
C9—C8—H8	119.9	C10—N2—Zn1	128.7 (3)
C7—C8—H8	119.9	C11—N2—Zn1	113.5 (3)
C8—C9—C10	119.3 (5)	C13—O1—Zn1	129.41 (19)
C8—C9—H9	120.3	H1B—O1W—H1A	96 (4)
C10—C9—H9	120.3	C20—O3—H3A	109.5
N2—C10—C9	122.6 (5)	O1—Zn1—O1ⁱ	106.16 (11)
N2—C10—H10	118.7	O1—Zn1—N1ⁱ	98.70 (10)
C9—C10—H10	118.7	O1ⁱ—Zn1—N1ⁱ	87.72 (10)
N2—C11—C7	122.7 (5)	O1—Zn1—N1	87.72 (10)
N2—C11—C12	117.1 (3)	O1ⁱ—Zn1—N1	98.70 (10)
C7—C11—C12	120.2 (5)	N1ⁱ—Zn1—N1	169.36 (16)
N1—C12—C4	122.4 (4)	O1—Zn1—N2	162.88 (11)
N1—C12—C11	117.8 (4)	O1ⁱ—Zn1—N2	82.94 (10)
C4—C12—C11	119.7 (4)	N1ⁱ—Zn1—N2	96.08 (12)
O1—C13—O2	123.8 (3)	N1—Zn1—N2	76.44 (13)
O1—C13—C14	118.1 (3)	O1—Zn1—N2ⁱ	82.94 (10)
O2—C13—C14	118.1 (3)	O1ⁱ—Zn1—N2ⁱ	162.88 (11)
C19—C14—C15	119.9 (3)	N1ⁱ—Zn1—N2ⁱ	76.44 (13)
C19—C14—C13	119.0 (3)	N1—Zn1—N2ⁱ	96.08 (12)
C15—C14—C13	121.0 (2)	N2—Zn1—N2ⁱ	92.23 (15)

N1—C1—C2—C3	−0.2 (7)	C16—C17—C20—O4	−176.6 (4)
C1—C2—C3—C4	1.7 (8)	C18—C17—C20—O3	−177.0 (3)
C2—C3—C4—C12	−1.5 (7)	C16—C17—C20—O3	3.8 (5)
C2—C3—C4—C5	178.1 (4)	C2—C1—N1—C12	−1.4 (6)
C3—C4—C5—C6	−177.5 (5)	C2—C1—N1—Zn1	179.3 (3)
C12—C4—C5—C6	2.2 (8)	C4—C12—N1—C1	1.6 (5)
C4—C5—C6—C7	−0.8 (9)	C11—C12—N1—C1	−176.8 (3)
C5—C6—C7—C8	177.4 (5)	C4—C12—N1—Zn1	−179.0 (3)
C5—C6—C7—C11	−1.3 (8)	C11—C12—N1—Zn1	2.6 (4)
C11—C7—C8—C9	0.1 (7)	C9—C10—N2—C11	2.0 (6)
C6—C7—C8—C9	−178.6 (5)	C9—C10—N2—Zn1	178.0 (3)
C7—C8—C9—C10	−1.2 (7)	C7—C11—N2—C10	−3.2 (5)
C8—C9—C10—N2	0.2 (7)	C12—C11—N2—C10	175.9 (3)
C8—C7—C11—N2	2.2 (6)	C7—C11—N2—Zn1	−179.8 (3)
C6—C7—C11—N2	−179.1 (4)	C12—C11—N2—Zn1	−0.8 (4)
C8—C7—C11—C12	−176.9 (4)	O2—C13—O1—Zn1	135.8 (3)
C6—C7—C11—C12	1.9 (6)	C14—C13—O1—Zn1	−42.9 (4)
C3—C4—C12—N1	−0.2 (6)	C13—O1—Zn1—O1ⁱ	63.6 (2)
C5—C4—C12—N1	−179.8 (4)	C13—O1—Zn1—N1ⁱ	−26.5 (3)
C3—C4—C12—C11	178.2 (4)	C13—O1—Zn1—N1	162.0 (3)
C5—C4—C12—C11	−1.5 (6)	C13—O1—Zn1—N2	−176.0 (3)
N2—C11—C12—N1	−1.2 (5)	C13—O1—Zn1—N2ⁱ	−101.6 (3)
C7—C11—C12—N1	177.9 (3)	C1—N1—Zn1—O1	−9.4 (3)
N2—C11—C12—C4	−179.6 (3)	C12—N1—Zn1—O1	171.3 (2)
C7—C11—C12—C4	−0.5 (6)	C1—N1—Zn1—O1ⁱ	96.6 (3)
O1—C13—C14—C19	134.7 (3)	C12—N1—Zn1—O1ⁱ	−82.7 (2)
O2—C13—C14—C19	−44.2 (4)	C1—N1—Zn1—N1ⁱ	−136.8 (3)
O1—C13—C14—C15	−40.9 (4)	C12—N1—Zn1—N1ⁱ	43.9 (2)
O2—C13—C14—C15	140.3 (3)	C1—N1—Zn1—N2	177.1 (3)
C19—C14—C15—C16	−4.1 (4)	C12—N1—Zn1—N2	−2.2 (2)
C13—C14—C15—C16	171.4 (3)	C1—N1—Zn1—N2ⁱ	−92.1 (3)
C19—C14—C15—C15ⁱ	172.4 (2)	C12—N1—Zn1—N2ⁱ	88.6 (2)
C13—C14—C15—C15ⁱ	−12.1 (4)	C10—N2—Zn1—O1	162.7 (3)
C14—C15—C16—C17	1.7 (4)	C11—N2—Zn1—O1	−21.1 (5)
C15ⁱ—C15—C16—C17	−175.0 (2)	C10—N2—Zn1—O1ⁱ	−73.9 (3)
C15—C16—C17—C18	1.1 (5)	C11—N2—Zn1—O1ⁱ	102.3 (2)
C15—C16—C17—C20	−179.8 (3)	C10—N2—Zn1—N1ⁱ	13.1 (3)
C16—C17—C18—C19	−1.3 (5)	C11—N2—Zn1—N1ⁱ	−170.7 (2)
C20—C17—C18—C19	179.5 (3)	C10—N2—Zn1—N1	−174.6 (3)
C17—C18—C19—C14	−1.1 (5)	C11—N2—Zn1—N1	1.6 (2)
C15—C14—C19—C18	3.9 (5)	C10—N2—Zn1—N2ⁱ	89.7 (3)
C13—C14—C19—C18	−171.7 (3)	C11—N2—Zn1—N2ⁱ	−94.1 (3)
C18—C17—C20—O4	2.6 (6)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱⁱ	0.82	1.74	2.538 (3)	162
O1W—H1B···O4ⁱⁱⁱ	0.86 (3)	2.24 (2)	2.966 (4)	143 (3)
O1W—H1A···O2	0.85 (3)	2.00 (2)	2.808 (4)	159 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O
M_r	790.03
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	16.901 (5), 9.473 (3), 22.126 (7)
β (°)	96.429 (5)
V (Å³)	3520.4 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.817, 0.853
No. of measured, independent and observed [I > 2σ(I)] reflections	9664, 3487, 2437
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.621

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.125, 1.04
No. of reflections	3487
No. of parameters	255
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.22

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

Selected geometric parameters (Å, º) top

Zn1—O1	2.102 (2)	Zn1—N2	2.199 (3)
Zn1—N1	2.130 (3)

O1—Zn1—O1ⁱ	106.16 (11)	N1—Zn1—N2	76.44 (13)
O1—Zn1—N1ⁱ	98.70 (10)	O1—Zn1—N2ⁱ	82.94 (10)
O1—Zn1—N1	87.72 (10)	N1—Zn1—N2ⁱ	96.08 (12)
N1ⁱ—Zn1—N1	169.36 (16)	N2—Zn1—N2ⁱ	92.23 (15)
O1—Zn1—N2	162.88 (11)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱⁱ	0.82	1.74	2.538 (3)	162
O1W—H1B···O4ⁱⁱⁱ	0.86 (3)	2.24 (2)	2.966 (4)	143 (3)
O1W—H1A···O2	0.85 (3)	2.00 (2)	2.808 (4)	159 (4)

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

Acknowledgements

The authors thank Changchun Normal University for supporting this work.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Che, G.-B., Liu, H., Liu, C.-B. & Liu, B. (2006). Acta Cryst. E62, m286–m288. Web of Science CSD CrossRef IUCr Journals Google Scholar
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