μ-2,5-Dihy­droxy­terephthalato-bis­[tri­aqua­(1,10-phenanthroline)zinc] dihy­droxy­terephthalate

Liu, H.; Liu, B.; Zhang, A.-P.; Li, C.-B.

doi:10.1107/S1600536812045837

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages m1503-m1504

doi:10.1107/S1600536812045837

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μ-2,5-Dihydroxyterephthalato-bis[triaqua(1,10-phenanthroline)zinc] dihydroxyterephthalate

Hong Liu,^a Bo Liu,^b Ai-Ping Zhang ^b and Chuan-Bi Li ^b ^*

^aDepartment of Information & Technology, Jilin Normal University, Siping 136000, People's Republic of China, and ^bDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: chuanbl@gmail.com

(Received 10 September 2012; accepted 6 November 2012; online 17 November 2012)

In the title compound, [Zn₂(C₈H₄O₆)(C₁₂H₈N₂)₂(H₂O)₆](C₈H₄O₆), the complete ions of both the binuclear dication and the dianion are generated by crystallographic inversion symmetry. The Zn atom is bonded to an N,N′-bidentate phenanthroline ligand, three water moleules and an O-monodenate 2,5-dihydroxyterephthalate dianion. In the resulting distorted octahedral ZnN₂O₄ coordination polyhedron, the water O atoms are in a mer orientation. Two intramolecular O—H⋯O hydrogen bonds occur in the bridging 2,5-dihydroxyterephthalate dianion within the complex cation and also in the free dianion. An intramolecular O_w—H⋯O (w = water) hydrogen bond also occurs within the dication. In the crystal, O—H⋯O hydrogen bonds link the component ions into a three-dimensional network.

Related literature

For a related structure, see: Sun et al. (2007 ). For background to the applications of coordination polymers, see: Perry et al. (2009 ).

Experimental

Crystal data

[Zn₂(C₈H₄O₆)(C₁₂H₈N₂)₂(H₂O)₆](C₈H₄O₆)
M_r = 991.46
Triclinic, $[P \overline 1]$
a = 8.765 (5) Å
b = 10.697 (5) Å
c = 11.062 (5) Å
α = 106.994 (5)°
β = 92.226 (5)°
γ = 90.977 (5)°
V = 990.7 (9) Å³
Z = 1
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 293 K
0.25 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.737, T_max = 0.829
5446 measured reflections
3824 independent reflections
3205 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.086
S = 1.04
3824 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.0181 (19)
Zn1—O1W	2.184 (2)
Zn1—O2W	2.1581 (19)
Zn1—O3W	2.113 (2)
Zn1—N1	2.124 (2)
Zn1—N2	2.156 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3ⁱ	0.97	1.95	2.902 (3)	170
O1W—H1WB⋯O2Wⁱⁱ	0.92	2.01	2.911 (3)	168
O2W—H2WA⋯O2	0.93	1.75	2.663 (3)	166
O3—H3A⋯O2ⁱⁱⁱ	0.82	1.84	2.562 (3)	147
O2W—H2WB⋯O5^iv	0.91	1.80	2.692 (3)	166
O3W—H3WA⋯O4	0.89	1.85	2.695 (3)	158
O3W—H3WB⋯O4^iv	0.83	1.82	2.650 (3)	175
O6—H6A⋯O5^v	0.82	1.84	2.566 (3)	146
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z; (iii) -x+2, -y, -z; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045837/hb6960sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045837/hb6960Isup2.hkl

checkCIF report

Comment top

The design and synthesis of coordination compounds have attracted much interest in the fields of supramolecular chemistry and crystal engineering because of their intriguing structural diversities and potential applications (Sun et al., 2007; Perry IV, et al., 2009). To extend the previous work, we obtained the title compound, (I), by using Zn^II, phenanthroline (phen) and 2,5-dihydroxyterephthalic acid (dhtp) as the starting materials.

The title compound, (I), is composed of a Zn^II canion, a phen molecule, half a coordinated dhtp anion, half a free dhtp anion and three coordinated water molecules in the asymmetric unit as shown in Fig. 1. Zn^II canion exhibits a distorted octahedral geometry, being coordinated by two N atoms of a phen molecule, one O atom from dhtp anion and three water O atoms. The Zn–O and Zn–N distances are normal. Zn^II canions are connected by dhtp anion to form a [Zn₂(phen)₂(dhtp)(H₂O)₆]^II cation unit. In additon, the free dhtp anion as the counter-ion presents in the sturcture. By way of O–H···O hydrogen bonding between the cation units and counter-anions, a three-dimensional network is formed (Fig. 2). The detailed hydrogen-bonding parameters are summarized in Table 1.

Related literature top

For a related structure, see: Sun et al. (2007). For background to the applications of coordination polymers, see: Perry et al. (2009).

Experimental top

A mixture of Zn(CH₃COO)₂^.2H₂O (0.2 mmol), phen (0.3 mmol) and dhtp (0.2 mmol) were dissolved in 15 ml water. The resulting solution was stirred for about 0.5 h at room temperature, sealed in a 25-ml Teflon-lined stainless steel autoclave and heated at 443 K for three days under autogenous pressure. Afterward, the reaction system was slowly cooled to room temperature and colourless blocks of the title compound were recovered.

Computing details top

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (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).

Figures top

	Fig. 1. A representation of title compound. Displacement ellipsoids are drawn at the 40% probability level. H atoms have been omitted for clarity. Unlabelled atoms are related to the reference atoms by the symmetry operations. [Symmetry codes: (i) - x + 2, - y, - z; (ii) - x + 1, - y, - z + 1].
	Fig. 2. The packing diagram of the title compound. All H-atoms except for those involved in hydrogen bonds are omitted for clarity. (hydrogen bonds indicated by dashed lines).

µ-2,5-Dihydroxyterephthalato-bis[triaqua(1,10-phenanthroline)zinc] dihydroxyterephthalate top

Crystal data top

[Zn₂(C₈H₄O₆)(C₁₂H₈N₂)₂(H₂O)₆](C₈H₄O₆)	Z = 1
M_r = 991.46	F(000) = 508
Triclinic, P1	D_x = 1.662 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.765 (5) Å	Cell parameters from 1867 reflections
b = 10.697 (5) Å	θ = 2.3–24.9°
c = 11.062 (5) Å	µ = 1.30 mm⁻¹
α = 106.994 (5)°	T = 293 K
β = 92.226 (5)°	Block, colorless
γ = 90.977 (5)°	0.25 × 0.18 × 0.15 mm
V = 990.7 (9) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	3205 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scan	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→5
T_min = 0.737, T_max = 0.829	k = −13→13
5446 measured reflections	l = −13→13

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0372P)² + 0.484P] where P = (F_o² + 2F_c²)/3
3824 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Zn₂(C₈H₄O₆)(C₁₂H₈N₂)₂(H₂O)₆](C₈H₄O₆)	γ = 90.977 (5)°
M_r = 991.46	V = 990.7 (9) Å³
Triclinic, P1	Z = 1
a = 8.765 (5) Å	Mo Kα radiation
b = 10.697 (5) Å	µ = 1.30 mm⁻¹
c = 11.062 (5) Å	T = 293 K
α = 106.994 (5)°	0.25 × 0.18 × 0.15 mm
β = 92.226 (5)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3824 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3205 reflections with I > 2σ(I)
T_min = 0.737, T_max = 0.829	R_int = 0.019
5446 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
3824 reflections	Δρ_min = −0.29 e Å⁻³
289 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.50422 (4)	0.32879 (3)	0.16460 (3)	0.03368 (11)
C1	0.4116 (3)	0.0549 (3)	0.1904 (3)	0.0410 (7)
H1	0.5020	0.0258	0.1515	0.049*
C2	0.3222 (4)	−0.0322 (3)	0.2306 (3)	0.0490 (8)
H2	0.3518	−0.1180	0.2177	0.059*
C3	0.1916 (4)	0.0092 (3)	0.2888 (3)	0.0534 (9)
H3	0.1321	−0.0478	0.3178	0.064*
C4	0.1455 (3)	0.1379 (3)	0.3054 (3)	0.0468 (8)
C5	0.0065 (4)	0.1877 (4)	0.3598 (3)	0.0634 (10)
H5	−0.0560	0.1351	0.3920	0.076*
C6	−0.0360 (4)	0.3089 (4)	0.3656 (3)	0.0643 (11)
H6	−0.1282	0.3382	0.4008	0.077*
C7	0.0574 (3)	0.3950 (3)	0.3186 (3)	0.0518 (8)
C8	0.0161 (4)	0.5197 (4)	0.3177 (3)	0.0677 (11)
H8	−0.0762	0.5528	0.3500	0.081*
C9	0.1111 (5)	0.5934 (4)	0.2692 (4)	0.0735 (12)
H9	0.0833	0.6761	0.2667	0.088*
C10	0.2505 (4)	0.5432 (3)	0.2235 (3)	0.0600 (9)
H10	0.3157	0.5949	0.1925	0.072*
C11	0.1974 (3)	0.3504 (3)	0.2684 (3)	0.0386 (6)
C12	0.2414 (3)	0.2194 (3)	0.2602 (2)	0.0357 (6)
C13	0.7999 (3)	0.2201 (3)	0.0587 (2)	0.0319 (6)
C14	0.9054 (3)	0.1076 (2)	0.0300 (2)	0.0274 (5)
C15	0.8650 (3)	−0.0063 (2)	0.0586 (2)	0.0300 (6)
H15	0.7743	−0.0104	0.0985	0.036*
C16	0.9569 (3)	−0.1134 (2)	0.0290 (2)	0.0296 (5)
C17	0.4052 (3)	0.2683 (3)	0.5940 (3)	0.0377 (6)
C18	0.4543 (3)	0.1290 (2)	0.5460 (2)	0.0307 (6)
C19	0.5797 (3)	0.0989 (2)	0.4716 (2)	0.0338 (6)
H19	0.6340	0.1660	0.4531	0.041*
C20	0.6264 (3)	−0.0285 (2)	0.4243 (2)	0.0334 (6)
N1	0.3740 (2)	0.1776 (2)	0.2049 (2)	0.0346 (5)
N2	0.2937 (3)	0.4250 (2)	0.2225 (2)	0.0419 (6)
O1	0.6766 (2)	0.20561 (17)	0.10775 (18)	0.0382 (4)
O2	0.8398 (2)	0.32217 (18)	0.0314 (2)	0.0447 (5)
O3	0.9102 (2)	−0.22265 (18)	0.0592 (2)	0.0461 (5)
H3A	0.9735	−0.2795	0.0370	0.069*
O4	0.4677 (3)	0.35176 (18)	0.5525 (2)	0.0592 (7)
O5	0.3055 (3)	0.29470 (18)	0.6758 (2)	0.0500 (5)
O6	0.7485 (3)	−0.05155 (19)	0.3502 (2)	0.0563 (6)
H6A	0.7647	−0.1301	0.3282	0.084*
O1W	0.4148 (2)	0.28676 (19)	−0.03067 (18)	0.0434 (5)
H1WA	0.3083	0.2617	−0.0317	0.052*
H1WB	0.4161	0.3598	−0.0582	0.052*
O2W	0.6253 (2)	0.49092 (17)	0.12905 (17)	0.0371 (4)
H2WA	0.7050	0.4415	0.0879	0.045*
H2WB	0.6629	0.5567	0.1971	0.045*
O3W	0.5968 (2)	0.39846 (17)	0.35216 (17)	0.0380 (4)
H3WA	0.5567	0.3612	0.4060	0.046*
H3WB	0.5806	0.4777	0.3793	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03234 (18)	0.02944 (18)	0.04078 (19)	0.00700 (12)	0.01051 (13)	0.01119 (13)
C1	0.0402 (16)	0.0353 (15)	0.0467 (17)	−0.0007 (13)	−0.0064 (13)	0.0120 (13)
C2	0.058 (2)	0.0409 (17)	0.0477 (18)	−0.0125 (15)	−0.0175 (16)	0.0160 (14)
C3	0.061 (2)	0.057 (2)	0.0446 (18)	−0.0277 (18)	−0.0106 (16)	0.0206 (16)
C4	0.0400 (17)	0.063 (2)	0.0343 (16)	−0.0155 (15)	−0.0036 (13)	0.0107 (14)
C5	0.044 (2)	0.091 (3)	0.050 (2)	−0.018 (2)	0.0094 (16)	0.011 (2)
C6	0.0291 (17)	0.102 (3)	0.048 (2)	−0.0024 (19)	0.0123 (15)	0.000 (2)
C7	0.0350 (16)	0.069 (2)	0.0410 (17)	0.0148 (16)	−0.0012 (13)	−0.0009 (15)
C8	0.047 (2)	0.085 (3)	0.057 (2)	0.029 (2)	0.0002 (17)	−0.002 (2)
C9	0.081 (3)	0.058 (2)	0.074 (3)	0.040 (2)	−0.002 (2)	0.007 (2)
C10	0.068 (2)	0.050 (2)	0.065 (2)	0.0224 (17)	0.0092 (18)	0.0192 (17)
C11	0.0307 (14)	0.0508 (17)	0.0319 (14)	0.0062 (13)	0.0012 (12)	0.0081 (13)
C12	0.0293 (14)	0.0456 (16)	0.0305 (14)	−0.0035 (12)	−0.0027 (11)	0.0093 (12)
C13	0.0296 (14)	0.0303 (14)	0.0331 (14)	0.0045 (11)	0.0008 (11)	0.0048 (11)
C14	0.0230 (12)	0.0291 (13)	0.0270 (12)	0.0053 (10)	0.0003 (10)	0.0033 (10)
C15	0.0215 (13)	0.0336 (14)	0.0340 (14)	0.0037 (10)	0.0072 (10)	0.0076 (11)
C16	0.0285 (13)	0.0277 (13)	0.0316 (13)	−0.0013 (11)	0.0006 (11)	0.0074 (11)
C17	0.0541 (18)	0.0248 (14)	0.0333 (14)	0.0011 (12)	0.0027 (13)	0.0068 (11)
C18	0.0399 (15)	0.0221 (12)	0.0296 (13)	0.0005 (11)	−0.0001 (11)	0.0071 (10)
C19	0.0412 (15)	0.0210 (12)	0.0387 (15)	−0.0053 (11)	0.0038 (12)	0.0081 (11)
C20	0.0379 (15)	0.0276 (13)	0.0349 (14)	0.0012 (11)	0.0051 (12)	0.0091 (11)
N1	0.0306 (12)	0.0355 (13)	0.0381 (12)	0.0005 (10)	0.0001 (10)	0.0115 (10)
N2	0.0410 (14)	0.0395 (13)	0.0450 (14)	0.0138 (11)	0.0050 (11)	0.0111 (11)
O1	0.0308 (10)	0.0313 (10)	0.0540 (12)	0.0106 (8)	0.0151 (9)	0.0124 (9)
O2	0.0440 (12)	0.0337 (11)	0.0599 (13)	0.0102 (9)	0.0169 (10)	0.0167 (10)
O3	0.0384 (11)	0.0346 (11)	0.0705 (14)	0.0081 (9)	0.0190 (10)	0.0211 (10)
O4	0.1041 (19)	0.0225 (10)	0.0548 (13)	0.0075 (11)	0.0337 (13)	0.0132 (9)
O5	0.0615 (14)	0.0293 (10)	0.0564 (13)	0.0071 (10)	0.0205 (11)	0.0058 (9)
O6	0.0590 (14)	0.0323 (11)	0.0774 (16)	0.0039 (10)	0.0363 (12)	0.0113 (11)
O1W	0.0437 (12)	0.0450 (11)	0.0452 (11)	0.0008 (9)	0.0007 (9)	0.0191 (9)
O2W	0.0425 (11)	0.0287 (10)	0.0407 (11)	0.0044 (8)	0.0081 (9)	0.0097 (8)
O3W	0.0471 (11)	0.0270 (9)	0.0401 (11)	0.0057 (8)	0.0097 (9)	0.0090 (8)

Geometric parameters (Å, º) top

Zn1—O1	2.0181 (19)	C11—C12	1.437 (4)
Zn1—O1W	2.184 (2)	C12—N1	1.356 (3)
Zn1—O2W	2.1581 (19)	C13—O1	1.255 (3)
Zn1—O3W	2.113 (2)	C13—O2	1.263 (3)
Zn1—N1	2.124 (2)	C13—C14	1.497 (3)
Zn1—N2	2.156 (2)	C14—C15	1.389 (4)
C1—N1	1.324 (3)	C14—C16ⁱ	1.402 (3)
C1—C2	1.388 (4)	C15—C16	1.380 (3)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.353 (5)	C16—O3	1.367 (3)
C2—H2	0.9300	C16—C14ⁱ	1.402 (3)
C3—C4	1.403 (5)	C17—O4	1.244 (3)
C3—H3	0.9300	C17—O5	1.258 (3)
C4—C12	1.407 (4)	C17—C18	1.505 (4)
C4—C5	1.422 (5)	C18—C19	1.384 (4)
C5—C6	1.339 (5)	C18—C20ⁱⁱ	1.401 (3)
C5—H5	0.9300	C19—C20	1.385 (4)
C6—C7	1.441 (5)	C19—H19	0.9300
C6—H6	0.9300	C20—O6	1.356 (3)
C7—C8	1.391 (5)	C20—C18ⁱⁱ	1.401 (3)
C7—C11	1.400 (4)	O3—H3A	0.8200
C8—C9	1.364 (6)	O6—H6A	0.8200
C8—H8	0.9300	O1W—H1WA	0.9650
C9—C10	1.397 (5)	O1W—H1WB	0.9182
C9—H9	0.9300	O2W—H2WA	0.9333
C10—N2	1.322 (4)	O2W—H2WB	0.9127
C10—H10	0.9300	O3W—H3WA	0.8873
C11—N2	1.362 (4)	O3W—H3WB	0.8287

O1—Zn1—O3W	93.06 (8)	C7—C11—C12	119.7 (3)
O1—Zn1—N1	90.52 (9)	N1—C12—C4	122.2 (3)
O3W—Zn1—N1	92.67 (8)	N1—C12—C11	117.9 (2)
O1—Zn1—N2	168.50 (8)	C4—C12—C11	119.9 (3)
O3W—Zn1—N2	90.35 (8)	O1—C13—O2	124.5 (2)
N1—Zn1—N2	78.34 (9)	O1—C13—C14	117.3 (2)
O1—Zn1—O2W	93.13 (8)	O2—C13—C14	118.2 (2)
O3W—Zn1—O2W	86.71 (7)	C15—C14—C16ⁱ	119.1 (2)
N1—Zn1—O2W	176.32 (8)	C15—C14—C13	119.7 (2)
N2—Zn1—O2W	98.03 (9)	C16ⁱ—C14—C13	121.2 (2)
O1—Zn1—O1W	90.61 (8)	C16—C15—C14	121.1 (2)
O3W—Zn1—O1W	171.35 (7)	C16—C15—H15	119.4
N1—Zn1—O1W	95.13 (8)	C14—C15—H15	119.4
N2—Zn1—O1W	87.58 (9)	O3—C16—C15	118.2 (2)
O2W—Zn1—O1W	85.27 (7)	O3—C16—C14ⁱ	122.0 (2)
N1—C1—C2	122.9 (3)	C15—C16—C14ⁱ	119.8 (2)
N1—C1—H1	118.6	O4—C17—O5	123.5 (3)
C2—C1—H1	118.6	O4—C17—C18	118.2 (3)
C3—C2—C1	119.2 (3)	O5—C17—C18	118.3 (2)
C3—C2—H2	120.4	C19—C18—C20ⁱⁱ	119.3 (2)
C1—C2—H2	120.4	C19—C18—C17	120.2 (2)
C2—C3—C4	120.3 (3)	C20ⁱⁱ—C18—C17	120.5 (2)
C2—C3—H3	119.9	C18—C19—C20	121.6 (2)
C4—C3—H3	119.9	C18—C19—H19	119.2
C3—C4—C12	117.0 (3)	C20—C19—H19	119.2
C3—C4—C5	124.0 (3)	O6—C20—C19	118.7 (2)
C12—C4—C5	119.0 (3)	O6—C20—C18ⁱⁱ	122.3 (2)
C6—C5—C4	121.2 (3)	C19—C20—C18ⁱⁱ	119.1 (2)
C6—C5—H5	119.4	C1—N1—C12	118.5 (2)
C4—C5—H5	119.4	C1—N1—Zn1	128.2 (2)
C5—C6—C7	121.7 (3)	C12—N1—Zn1	113.14 (18)
C5—C6—H6	119.1	C10—N2—C11	118.1 (3)
C7—C6—H6	119.1	C10—N2—Zn1	129.8 (2)
C8—C7—C11	117.5 (3)	C11—N2—Zn1	112.08 (18)
C8—C7—C6	124.1 (3)	C13—O1—Zn1	131.20 (17)
C11—C7—C6	118.4 (3)	C16—O3—H3A	109.5
C9—C8—C7	119.9 (3)	C20—O6—H6A	109.5
C9—C8—H8	120.1	Zn1—O1W—H1WA	107.0
C7—C8—H8	120.1	Zn1—O1W—H1WB	112.0
C8—C9—C10	119.3 (3)	H1WA—O1W—H1WB	105.5
C8—C9—H9	120.4	Zn1—O2W—H2WA	95.5
C10—C9—H9	120.4	Zn1—O2W—H2WB	118.0
N2—C10—C9	122.6 (4)	H2WA—O2W—H2WB	110.3
N2—C10—H10	118.7	Zn1—O3W—H3WA	114.7
C9—C10—H10	118.7	Zn1—O3W—H3WB	108.4
N2—C11—C7	122.6 (3)	H3WA—O3W—H3WB	106.6
N2—C11—C12	117.6 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3ⁱⁱⁱ	0.97	1.95	2.902 (3)	170
O1W—H1WB···O2W^iv	0.92	2.01	2.911 (3)	168
O2W—H2WA···O2	0.93	1.75	2.663 (3)	166
O3—H3A···O2ⁱ	0.82	1.84	2.562 (3)	147
O2W—H2WB···O5^v	0.91	1.80	2.692 (3)	166
O3W—H3WA···O4	0.89	1.85	2.695 (3)	158
O3W—H3WB···O4^v	0.83	1.82	2.650 (3)	175
O6—H6A···O5ⁱⁱ	0.82	1.84	2.566 (3)	146

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₈H₄O₆)(C₁₂H₈N₂)₂(H₂O)₆](C₈H₄O₆)
M_r	991.46
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.765 (5), 10.697 (5), 11.062 (5)
α, β, γ (°)	106.994 (5), 92.226 (5), 90.977 (5)
V (Å³)	990.7 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.25 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.737, 0.829
No. of measured, independent and observed [I > 2σ(I)] reflections	5446, 3824, 3205
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.086, 1.04
No. of reflections	3824
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.29

Computer programs: APEX2 (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Selected bond lengths (Å) top

Zn1—O1	2.0181 (19)	Zn1—O3W	2.113 (2)
Zn1—O1W	2.184 (2)	Zn1—N1	2.124 (2)
Zn1—O2W	2.1581 (19)	Zn1—N2	2.156 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3ⁱ	0.97	1.95	2.902 (3)	170
O1W—H1WB···O2Wⁱⁱ	0.92	2.01	2.911 (3)	168
O2W—H2WA···O2	0.93	1.75	2.663 (3)	166
O3—H3A···O2ⁱⁱⁱ	0.82	1.84	2.562 (3)	147
O2W—H2WB···O5^iv	0.91	1.80	2.692 (3)	166
O3W—H3WA···O4	0.89	1.85	2.695 (3)	158
O3W—H3WB···O4^iv	0.83	1.82	2.650 (3)	175
O6—H6A···O5^v	0.82	1.84	2.566 (3)	146

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

Acknowledgements

The authors thank Jilin Normal University for supporting this study.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact BbR, Bonn, Germany. Google Scholar
Bruker (2002). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Perry, J. J. IV, Perman, J. A. & Zaworotko, M. J. (2009). Chem. Soc. Rev. 38, 1400–1417. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y. G., Gao, E. J. & Wei, D. Z. (2007). Inorg. Chem. Commun. 10, 467–470. Web of Science CSD CrossRef CAS Google Scholar

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Volume 68| Part 12| December 2012| Pages m1503-m1504

doi:10.1107/S1600536812045837

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

μ-2,5-Dihy­dr­oxy­terephthalato-bis­­[tri­aqua­(1,10-phenanthroline)zinc] dihy­dr­oxy­terephthalate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

μ-2,5-Dihydroxyterephthalato-bis[triaqua(1,10-phenanthroline)zinc] dihydroxyterephthalate