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

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ISSN: 2056-9890

(5,5′-Di­methyl-2,2′-bi­pyridine-κ2N,N′)(1-naphthyl­acetato-κO)(1-naphthyl­acetato-κ2O,O′)zinc hemihydrate

aEnvironment Science and Engineering, Donghua University, Shanghai 200051, People's Republic of China, and bCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China
*Correspondence e-mail: liujianshe@dhu.edu.cn

(Received 22 March 2011; accepted 9 April 2011; online 16 April 2011)

In the title compound, [Zn(C12H9O2)2(C12H12N2)]·0.5H2O, the water mol­ecule lies on a twofold rotation axis. The ZnII atom is coordinated by three O atoms from two 1-naphthyl­acetate ligands, one monodentate and the other asymmetric bidentate chelate, and two N atoms from a 5,5′-dimethyl-2,2′-bipyridine ligand, giving an irregular environment. In the crystal, the complex mol­ecules are inter­linked through the water mol­ecule by O—H⋯Ocarboxyl­ate hydrogen bonds, together with weak C—H⋯O and bipyridine ring ππ stacking inter­actions [ring centroid separation = 3.761 (2) Å], giving a two-dimensional network structure.

Related literature

For background to self-assembly of supra­molecular architectures based on naphthyl­carboxyl­ate ligands, see: Kong et al. (2009[Kong, Z. G., Wang, X. Y. & Carlucci, L. (2009). Inorg. Chem. Commun. 12, 691-694]); Li et al. (2009[Li, Y.-P., Sun, D.-J., Zang, H., Su, G.-F. & Li, Y.-L. (2009). Acta Cryst. C65, m340-m342.]). The Zn—O distance in the second ligand [2.417 (3) Å] suggests a non-negligible (bidentate) inter­action, see: Guilera & Steed (1999[Guilera, G. & Steed, J. W. (1999). Chem. Commun. 6, 1294-1296.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C12H9O2)2(C12H12N2)]·0.5H2O

  • Mr = 629.00

  • Monoclinic, C 2/c

  • a = 32.212 (7) Å

  • b = 8.2668 (17) Å

  • c = 25.314 (5) Å

  • β = 117.865 (4)°

  • V = 5959 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.87 mm−1

  • T = 296 K

  • 0.30 × 0.28 × 0.21 mm

Data collection
  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.756, Tmax = 0.819

  • 21468 measured reflections

  • 5325 independent reflections

  • 3566 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.106

  • S = 0.99

  • 5325 reflections

  • 395 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5⋯O1 0.82 2.21 2.948 (3) 150
C8—H8A⋯O4i 0.93 2.59 3.515 (6) 171
Symmetry code: (i) [x, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Self-assembly of supramolecular architectures based on naphthylcarboxylate ligands has attracted much attention during recent decades (Kong et al., 2009; Li et al., 2009). However, to our knowledge, 1-naphthylacetic acid has not been used as a potential building block in the construction of supramolecular architectures. Herein we report the structure of the title compound, the mixed ligand complex [(C12H12N2)(C12H9O2)2]2 . 0.5H2O (I), from the reaction of zinc nitrate with 1-naphthylacetic acid and 5,5'-dimethyl-2,2'-bipyridyrine in a basic aqueous solution.

The asymmetric unit in (I) (Fig. 1) consists of one ZnII complex unit and a water molecule which lies on a two-fold rotation axis (Fig. 1). The five-coordinate Zn centre comprises three O atoms from two 1-naphthylacetate ligands and two N atoms from a 5,5'-dimethyl-2,2'-bipyridyrine ligand. There are two coordination modes for the 1-naphthylacetate ligands in the structure: one monodentate the other asymmetric bidentate chelate. The Zn1-O4 distance in the second ligand [2.417 (3) Å] suggests a non-negligible (bidentate) interaction (Guilera & Steed, 1999) whereas the Zn1—O5 distance in the first ligand [2.587 (3)] is considered beyond the distance maximum for a bidentate interaction. In the crystal, the supramolecular network is stabilized by water O—H···Ocarboxyl, hydrogen bonds together with weak intermolecular aromatic C8—H···Ocarboxyl interactions (Table 1), giving a two-dimensional network structure. In addition the inter-ring separation between the pyridine rings of two adjacent 5,5'-dimethyl-2,2'-bipyridine ligands is 3.761 (2) Å, indicating weak π-π stacking interactions (Fig. 2).

Related literature top

For background to self-assembly of supramolecular architectures based on naphthylcarboxylate ligands, see: Kong et al. (2009); Li et al. (2009). The Zn—O distance in the second ligand [2.417 (3) Å] suggests a non-negligible (bidentate) interaction, see: Guilera & Steed (1999).

Experimental top

A mixture of 1-naphthylacetic acid (0.110 g, 0.5 mmol), 5,5'-dimethyl-2,2'-bipyridine (0.092 g, 0.5 mmol), zinc nitrate hexahydrate (0.075 g, 0.25 mmol), NaOH (0.08 g, 0.2 mmol) and water (10 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 423 K for 3 days, and then cooled to room temperature at a rate of 10 K h-1. The colorless crystals obtained were washed with water and dried in air (yield 47% based on zinc).

Refinement top

All H atoms were located from difference maps, and were treated as riding atoms with O—H = 0.82 Å and C—H = 0.93, 0.96 and 0.97 Å, for aryl, methyl and methine groups respectively, and with Uiso(H) = 1.5Ueq (methyl C-atoms) and 1.2Ueq(non-methyl C-atoms or water O-atom).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atom numbering scheme. The water molecule of solvation (O5) lies on a twofold rotation axis. Non-H atoms are shown with 30% probability displacement ellipsoids and H atoms are omitted.
[Figure 2] Fig. 2. A view of the three-dimensional network in (I) showing O—H···O, C—H···O and π-π stacking interactions as dashed lines.
(5,5'-Dimethyl-2,2'-bipyridine-κ2N,N')(1-naphthylacetato- κO)(1-naphthylacetato-κ2O,O')zinc hemihydrate top
Crystal data top
[Zn(C12H9O2)2(C12H12N2)]·0.5H2OF(000) = 2616
Mr = 629.00Dx = 1.402 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5837 reflections
a = 32.212 (7) Åθ = 2.8–27.9°
b = 8.2668 (17) ŵ = 0.87 mm1
c = 25.314 (5) ÅT = 296 K
β = 117.865 (4)°Block, colorless
V = 5959 (2) Å30.30 × 0.28 × 0.21 mm
Z = 8
Data collection top
Bruker APEXII area-detector
diffractometer
5325 independent reflections
Radiation source: fine-focus sealed tube3566 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 25.2°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3838
Tmin = 0.756, Tmax = 0.819k = 99
21468 measured reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0328P)2 + 11.176P]
where P = (Fo2 + 2Fc2)/3
5325 reflections(Δ/σ)max = 0.020
395 parametersΔρmax = 0.45 e Å3
2 restraintsΔρmin = 0.30 e Å3
Crystal data top
[Zn(C12H9O2)2(C12H12N2)]·0.5H2OV = 5959 (2) Å3
Mr = 629.00Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.212 (7) ŵ = 0.87 mm1
b = 8.2668 (17) ÅT = 296 K
c = 25.314 (5) Å0.30 × 0.28 × 0.21 mm
β = 117.865 (4)°
Data collection top
Bruker APEXII area-detector
diffractometer
5325 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3566 reflections with I > 2σ(I)
Tmin = 0.756, Tmax = 0.819Rint = 0.049
21468 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0442 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0328P)2 + 11.176P]
where P = (Fo2 + 2Fc2)/3
5325 reflectionsΔρmax = 0.45 e Å3
395 parametersΔρmin = 0.30 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
Zn10.120445 (14)0.34832 (5)0.280713 (17)0.04660 (14)
O10.07142 (9)0.4782 (3)0.21694 (10)0.0619 (6)
O20.12780 (10)0.4724 (3)0.19164 (11)0.0687 (7)
O30.18066 (9)0.4490 (3)0.34162 (11)0.0691 (7)
O40.12345 (12)0.5188 (4)0.35996 (13)0.0879 (10)
N10.08321 (9)0.1801 (3)0.30436 (11)0.0448 (7)
N20.14254 (9)0.1318 (3)0.26096 (11)0.0442 (6)
C10.08888 (14)0.5173 (4)0.18284 (15)0.0533 (9)
C20.05863 (14)0.6281 (5)0.13114 (16)0.0660 (11)
H2A0.02690.58560.11200.079*
H2B0.05760.73350.14730.079*
C30.07433 (12)0.6504 (5)0.08408 (17)0.0647 (11)
C40.09184 (16)0.7942 (6)0.0771 (2)0.0952 (16)
H4A0.09460.88060.10210.114*
C50.10634 (18)0.8141 (8)0.0303 (3)0.107 (2)
H5A0.11820.91180.02490.129*
C60.10167 (19)0.6813 (9)0.0053 (3)0.108 (2)
H6A0.11060.69280.03500.130*
C70.08495 (14)0.5357 (7)0.00033 (18)0.0784 (12)
C80.08172 (16)0.4032 (8)0.03669 (19)0.0912 (16)
H8A0.09050.41420.06670.109*
C90.06576 (19)0.2613 (9)0.0279 (2)0.1072 (19)
H9A0.06440.17350.05160.129*
C100.05146 (17)0.2409 (8)0.0143 (2)0.1002 (16)
H10A0.04020.14080.01870.120*
C110.05356 (14)0.3666 (6)0.05021 (18)0.0737 (12)
H11A0.04330.35120.07860.088*
C120.07062 (12)0.5175 (6)0.04549 (15)0.0641 (11)
C130.16592 (17)0.5149 (4)0.37445 (16)0.0638 (11)
C140.20119 (15)0.5898 (5)0.43349 (15)0.0676 (12)
H14A0.19160.56640.46380.081*
H14B0.23170.54090.44600.081*
C150.20519 (12)0.7702 (4)0.42897 (13)0.0492 (9)
C160.17724 (13)0.8677 (6)0.44192 (16)0.0655 (11)
H16A0.15600.82030.45250.079*
C170.17903 (17)1.0338 (6)0.44005 (19)0.0818 (14)
H17A0.15941.09640.44950.098*
C180.20899 (19)1.1047 (5)0.42461 (18)0.0820 (14)
H18A0.20971.21700.42300.098*
C190.23921 (14)1.0145 (5)0.41079 (15)0.0629 (11)
C200.2712 (2)1.0871 (8)0.3958 (2)0.1019 (19)
H20A0.27221.19930.39380.122*
C210.3005 (2)0.9985 (12)0.3841 (2)0.116 (2)
H21A0.32111.05040.37340.140*
C220.30117 (18)0.8311 (11)0.3874 (2)0.111 (2)
H22A0.32290.77230.38070.133*
C230.26923 (15)0.7514 (7)0.40089 (16)0.0795 (13)
H23A0.26870.63900.40180.095*
C240.23771 (12)0.8422 (5)0.41318 (13)0.0525 (9)
C250.05275 (12)0.2135 (5)0.32507 (14)0.0537 (9)
H25A0.04770.32130.33080.064*
C260.02851 (12)0.0962 (5)0.33832 (14)0.0535 (9)
C270.03634 (12)0.0623 (5)0.32856 (15)0.0577 (10)
H27A0.02020.14480.33610.069*
C280.06785 (12)0.0999 (4)0.30777 (15)0.0514 (9)
H28A0.07330.20700.30150.062*
C290.09120 (11)0.0246 (4)0.29648 (13)0.0412 (7)
C300.12614 (11)0.0026 (4)0.27505 (13)0.0401 (7)
C310.14199 (12)0.1536 (4)0.26986 (14)0.0496 (8)
H31A0.13040.24560.27950.060*
C320.17511 (12)0.1673 (5)0.25029 (15)0.0571 (9)
H32A0.18590.26900.24670.069*
C330.19239 (13)0.0319 (5)0.23602 (16)0.0575 (9)
C340.17446 (12)0.1158 (4)0.24173 (16)0.0537 (9)
H34A0.18530.20890.23160.064*
C350.00465 (14)0.1416 (6)0.36237 (18)0.0762 (12)
H35A0.03210.07420.34440.114*
H35B0.01370.25290.35320.114*
H35C0.01060.12670.40490.114*
C360.22968 (16)0.0420 (6)0.2159 (2)0.0877 (14)
H36A0.22150.12490.18620.131*
H36B0.25940.06750.24950.131*
H36C0.23190.06010.19930.131*
O50.00000.5928 (8)0.25000.233 (5)
H50.02030.53360.24960.350*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0513 (2)0.0329 (2)0.0490 (2)0.0034 (2)0.01794 (17)0.00328 (19)
O10.0735 (16)0.0611 (17)0.0491 (13)0.0086 (12)0.0271 (12)0.0098 (11)
O20.0709 (18)0.0643 (18)0.0627 (16)0.0214 (15)0.0243 (14)0.0167 (14)
O30.0811 (19)0.0525 (17)0.0566 (15)0.0065 (14)0.0180 (15)0.0072 (13)
O40.087 (2)0.093 (2)0.0689 (18)0.030 (2)0.0246 (17)0.0223 (17)
N10.0496 (16)0.0399 (17)0.0419 (14)0.0014 (13)0.0189 (13)0.0009 (12)
N20.0438 (15)0.0358 (16)0.0497 (15)0.0030 (13)0.0191 (13)0.0008 (13)
C10.073 (3)0.039 (2)0.0403 (19)0.0021 (19)0.0200 (19)0.0002 (16)
C20.073 (3)0.064 (3)0.057 (2)0.021 (2)0.027 (2)0.014 (2)
C30.052 (2)0.067 (3)0.064 (2)0.014 (2)0.0175 (19)0.033 (2)
C40.088 (3)0.080 (4)0.097 (4)0.015 (3)0.027 (3)0.035 (3)
C50.091 (4)0.102 (5)0.125 (5)0.003 (3)0.048 (4)0.065 (4)
C60.085 (4)0.127 (6)0.109 (4)0.017 (4)0.043 (3)0.064 (4)
C70.059 (3)0.112 (4)0.061 (3)0.021 (3)0.026 (2)0.028 (2)
C80.071 (3)0.152 (5)0.050 (2)0.031 (3)0.028 (2)0.014 (3)
C90.095 (4)0.149 (6)0.066 (3)0.017 (4)0.028 (3)0.002 (4)
C100.090 (4)0.114 (5)0.083 (3)0.006 (3)0.029 (3)0.014 (3)
C110.067 (3)0.090 (3)0.061 (2)0.002 (3)0.028 (2)0.000 (3)
C120.045 (2)0.102 (4)0.042 (2)0.018 (2)0.0176 (17)0.022 (2)
C130.091 (3)0.035 (2)0.042 (2)0.013 (2)0.011 (2)0.0039 (17)
C140.089 (3)0.047 (2)0.0400 (19)0.020 (2)0.0077 (19)0.0006 (16)
C150.052 (2)0.046 (2)0.0334 (17)0.0076 (17)0.0067 (16)0.0008 (15)
C160.055 (2)0.077 (3)0.051 (2)0.002 (2)0.0142 (18)0.008 (2)
C170.075 (3)0.074 (3)0.073 (3)0.021 (3)0.014 (2)0.011 (3)
C180.099 (4)0.044 (2)0.061 (3)0.008 (3)0.003 (3)0.003 (2)
C190.064 (3)0.059 (3)0.044 (2)0.019 (2)0.0076 (19)0.0078 (18)
C200.092 (4)0.118 (5)0.067 (3)0.045 (4)0.013 (3)0.015 (3)
C210.076 (4)0.185 (8)0.075 (4)0.045 (5)0.025 (3)0.006 (5)
C220.065 (3)0.198 (8)0.064 (3)0.002 (4)0.025 (2)0.019 (4)
C230.070 (3)0.109 (4)0.050 (2)0.004 (3)0.020 (2)0.015 (2)
C240.0480 (19)0.064 (2)0.0318 (16)0.0043 (19)0.0071 (15)0.0030 (17)
C250.058 (2)0.050 (2)0.050 (2)0.0059 (18)0.0224 (18)0.0012 (17)
C260.049 (2)0.064 (3)0.0421 (19)0.0022 (18)0.0167 (17)0.0041 (17)
C270.053 (2)0.062 (3)0.053 (2)0.0085 (19)0.0199 (18)0.0090 (19)
C280.052 (2)0.040 (2)0.058 (2)0.0038 (16)0.0228 (18)0.0003 (16)
C290.0428 (19)0.0373 (18)0.0340 (16)0.0004 (15)0.0101 (14)0.0013 (14)
C300.0405 (18)0.0328 (17)0.0363 (16)0.0014 (14)0.0091 (14)0.0019 (14)
C310.057 (2)0.0340 (18)0.0529 (19)0.0014 (17)0.0214 (17)0.0010 (17)
C320.062 (2)0.044 (2)0.065 (2)0.0070 (19)0.0292 (19)0.0030 (18)
C330.060 (2)0.053 (2)0.064 (2)0.0037 (19)0.032 (2)0.0004 (19)
C340.055 (2)0.043 (2)0.066 (2)0.0055 (17)0.0298 (19)0.0020 (17)
C350.070 (3)0.095 (3)0.076 (3)0.014 (3)0.045 (2)0.010 (3)
C360.098 (3)0.076 (3)0.122 (4)0.015 (3)0.079 (3)0.010 (3)
O50.134 (5)0.083 (5)0.495 (15)0.0000.157 (8)0.000
Geometric parameters (Å, º) top
Zn1—O11.967 (2)C16—C171.376 (6)
Zn1—O32.009 (3)C16—H16A0.9300
Zn1—N22.072 (3)C17—C181.334 (6)
Zn1—N12.098 (3)C17—H17A0.9300
Zn1—O42.416 (3)C18—C191.394 (6)
O1—C11.273 (4)C18—H18A0.9300
O2—C11.224 (4)C19—C201.391 (6)
O3—C131.258 (5)C19—C241.427 (5)
O4—C131.240 (5)C20—C211.333 (8)
N1—C291.344 (4)C20—H20A0.9300
N1—C251.340 (4)C21—C221.386 (9)
N2—C341.334 (4)C21—H21A0.9300
N2—C301.348 (4)C22—C231.392 (7)
C1—C21.520 (5)C22—H22A0.9300
C2—C31.507 (5)C23—C241.410 (5)
C2—H2A0.9700C23—H23A0.9300
C2—H2B0.9700C25—C261.381 (5)
C3—C41.363 (6)C25—H25A0.9300
C3—C121.437 (6)C26—C271.378 (5)
C4—C51.470 (7)C26—C351.503 (5)
C4—H4A0.9300C27—C281.379 (5)
C5—C61.383 (8)C27—H27A0.9300
C5—H5A0.9300C28—C291.381 (4)
C6—C71.352 (7)C28—H28A0.9300
C6—H6A0.9300C29—C301.477 (4)
C7—C81.414 (7)C30—C311.378 (4)
C7—C121.427 (5)C31—C321.375 (5)
C8—C91.340 (8)C31—H31A0.9300
C8—H8A0.9300C32—C331.372 (5)
C9—C101.356 (7)C32—H32A0.9300
C9—H9A0.9300C33—C341.387 (5)
C10—C111.362 (6)C33—C361.509 (5)
C10—H10A0.9300C34—H34A0.9300
C11—C121.391 (6)C35—H35A0.9600
C11—H11A0.9300C35—H35B0.9600
C13—C141.523 (5)C35—H35C0.9600
C14—C151.505 (5)C36—H36A0.9600
C14—H14A0.9700C36—H36B0.9600
C14—H14B0.9700C36—H36C0.9600
C15—C161.358 (5)O5—H50.8199
C15—C241.415 (5)
O1—Zn1—O3121.37 (11)C15—C16—C17122.7 (4)
O1—Zn1—N2120.53 (10)C15—C16—H16A118.6
O3—Zn1—N2103.04 (11)C17—C16—H16A118.6
O1—Zn1—N1104.43 (11)C18—C17—C16119.7 (5)
O3—Zn1—N1122.09 (10)C18—C17—H17A120.1
N2—Zn1—N178.64 (11)C16—C17—H17A120.1
O1—Zn1—O493.91 (11)C17—C18—C19121.6 (4)
O3—Zn1—O458.10 (11)C17—C18—H18A119.2
N2—Zn1—O4145.01 (11)C19—C18—H18A119.2
N1—Zn1—O487.49 (11)C20—C19—C18122.1 (5)
C1—O1—Zn1104.8 (2)C20—C19—C24119.1 (5)
C13—O3—Zn199.2 (3)C18—C19—C24118.8 (4)
C13—O4—Zn180.9 (2)C21—C20—C19121.1 (6)
C29—N1—C25118.7 (3)C21—C20—H20A119.5
C29—N1—Zn1114.6 (2)C19—C20—H20A119.5
C25—N1—Zn1126.6 (2)C20—C21—C22121.8 (6)
C34—N2—C30118.6 (3)C20—C21—H21A119.1
C34—N2—Zn1125.8 (2)C22—C21—H21A119.1
C30—N2—Zn1115.3 (2)C21—C22—C23119.8 (6)
O2—C1—O1122.7 (3)C21—C22—H22A120.1
O2—C1—C2122.0 (3)C23—C22—H22A120.1
O1—C1—C2115.4 (3)C22—C23—C24119.5 (5)
C3—C2—C1115.9 (3)C22—C23—H23A120.2
C3—C2—H2A108.3C24—C23—H23A120.2
C1—C2—H2A108.3C23—C24—C15122.9 (4)
C3—C2—H2B108.3C23—C24—C19118.7 (4)
C1—C2—H2B108.3C15—C24—C19118.4 (4)
H2A—C2—H2B107.4N1—C25—C26123.5 (3)
C4—C3—C12119.1 (4)N1—C25—H25A118.3
C4—C3—C2121.5 (5)C26—C25—H25A118.3
C12—C3—C2119.4 (4)C27—C26—C25116.9 (3)
C3—C4—C5120.6 (5)C27—C26—C35122.3 (4)
C3—C4—H4A119.7C25—C26—C35120.8 (4)
C5—C4—H4A119.7C26—C27—C28120.8 (4)
C6—C5—C4117.2 (5)C26—C27—H27A119.6
C6—C5—H5A121.4C28—C27—H27A119.6
C4—C5—H5A121.4C27—C28—C29118.7 (3)
C7—C6—C5124.4 (6)C27—C28—H28A120.7
C7—C6—H6A117.8C29—C28—H28A120.7
C5—C6—H6A117.8N1—C29—C28121.4 (3)
C6—C7—C8122.0 (5)N1—C29—C30115.6 (3)
C6—C7—C12118.1 (5)C28—C29—C30123.0 (3)
C8—C7—C12119.9 (5)N2—C30—C31120.9 (3)
C9—C8—C7118.9 (5)N2—C30—C29115.6 (3)
C9—C8—H8A120.6C31—C30—C29123.5 (3)
C7—C8—H8A120.6C32—C31—C30119.6 (3)
C8—C9—C10122.6 (6)C32—C31—H31A120.2
C8—C9—H9A118.7C30—C31—H31A120.2
C10—C9—H9A118.7C31—C32—C33120.4 (4)
C9—C10—C11120.1 (6)C31—C32—H32A119.8
C9—C10—H10A120.0C33—C32—H32A119.8
C11—C10—H10A120.0C32—C33—C34116.8 (3)
C10—C11—C12121.7 (5)C32—C33—C36121.9 (4)
C10—C11—H11A119.1C34—C33—C36121.3 (4)
C12—C11—H11A119.1N2—C34—C33123.8 (3)
C11—C12—C7116.9 (5)N2—C34—H34A118.1
C11—C12—C3122.5 (4)C33—C34—H34A118.1
C7—C12—C3120.6 (4)C26—C35—H35A109.5
O4—C13—O3121.4 (4)C26—C35—H35B109.5
O4—C13—C14119.6 (4)H35A—C35—H35B109.5
O3—C13—C14119.1 (4)C26—C35—H35C109.5
C15—C14—C13112.3 (3)H35A—C35—H35C109.5
C15—C14—H14A109.1H35B—C35—H35C109.5
C13—C14—H14A109.1C33—C36—H36A109.5
C15—C14—H14B109.1C33—C36—H36B109.5
C13—C14—H14B109.1H36A—C36—H36B109.5
H14A—C14—H14B107.9C33—C36—H36C109.5
C16—C15—C24118.7 (4)H36A—C36—H36C109.5
C16—C15—C14118.7 (4)H36B—C36—H36C109.5
C24—C15—C14122.6 (4)
O3—Zn1—O1—C169.3 (3)Zn1—O3—C13—O47.8 (4)
N2—Zn1—O1—C162.5 (3)Zn1—O3—C13—C14171.6 (3)
N1—Zn1—O1—C1147.6 (2)O4—C13—C14—C1581.9 (5)
O4—Zn1—O1—C1124.0 (2)O3—C13—C14—C1598.7 (4)
O1—Zn1—O3—C1377.4 (2)C13—C14—C15—C1691.5 (4)
N2—Zn1—O3—C13143.8 (2)C13—C14—C15—C2490.0 (5)
N1—Zn1—O3—C1359.2 (3)C24—C15—C16—C170.3 (5)
O4—Zn1—O3—C134.0 (2)C14—C15—C16—C17178.8 (3)
O1—Zn1—O4—C13128.9 (2)C15—C16—C17—C180.5 (6)
O3—Zn1—O4—C134.1 (2)C16—C17—C18—C190.7 (6)
N2—Zn1—O4—C1360.8 (3)C17—C18—C19—C20178.7 (4)
N1—Zn1—O4—C13126.8 (2)C17—C18—C19—C240.2 (6)
O1—Zn1—N1—C29119.4 (2)C18—C19—C20—C21178.4 (4)
O3—Zn1—N1—C2997.9 (2)C24—C19—C20—C210.5 (6)
N2—Zn1—N1—C290.5 (2)C19—C20—C21—C221.2 (8)
O4—Zn1—N1—C29147.2 (2)C20—C21—C22—C232.7 (8)
O1—Zn1—N1—C2559.6 (3)C21—C22—C23—C242.4 (7)
O3—Zn1—N1—C2583.1 (3)C22—C23—C24—C15178.1 (3)
N2—Zn1—N1—C25178.5 (3)C22—C23—C24—C190.7 (5)
O4—Zn1—N1—C2533.8 (3)C16—C15—C24—C23177.9 (3)
O1—Zn1—N2—C3483.3 (3)C14—C15—C24—C230.5 (5)
O3—Zn1—N2—C3455.9 (3)C16—C15—C24—C190.8 (4)
N1—Zn1—N2—C34176.6 (3)C14—C15—C24—C19179.3 (3)
O4—Zn1—N2—C34108.0 (3)C20—C19—C24—C230.8 (5)
O1—Zn1—N2—C30103.9 (2)C18—C19—C24—C23178.2 (3)
O3—Zn1—N2—C30116.9 (2)C20—C19—C24—C15179.5 (3)
N1—Zn1—N2—C303.7 (2)C18—C19—C24—C150.6 (5)
O4—Zn1—N2—C3064.9 (3)C29—N1—C25—C260.7 (5)
Zn1—O1—C1—O21.7 (4)Zn1—N1—C25—C26178.3 (2)
Zn1—O1—C1—C2176.5 (3)N1—C25—C26—C270.8 (5)
O2—C1—C2—C312.7 (6)N1—C25—C26—C35179.0 (3)
O1—C1—C2—C3169.0 (3)C25—C26—C27—C281.4 (5)
C1—C2—C3—C4110.8 (4)C35—C26—C27—C28178.5 (3)
C1—C2—C3—C1269.5 (5)C26—C27—C28—C290.5 (5)
C12—C3—C4—C50.6 (6)C25—N1—C29—C281.7 (4)
C2—C3—C4—C5179.2 (4)Zn1—N1—C29—C28177.4 (2)
C3—C4—C5—C60.4 (7)C25—N1—C29—C30178.4 (3)
C4—C5—C6—C70.3 (8)Zn1—N1—C29—C302.5 (3)
C5—C6—C7—C8178.9 (5)C27—C28—C29—N11.1 (5)
C5—C6—C7—C120.7 (8)C27—C28—C29—C30179.0 (3)
C6—C7—C8—C9178.6 (5)C34—N2—C30—C310.1 (4)
C12—C7—C8—C91.0 (7)Zn1—N2—C30—C31173.3 (2)
C7—C8—C9—C101.7 (8)C34—N2—C30—C29179.5 (3)
C8—C9—C10—C110.8 (8)Zn1—N2—C30—C296.1 (3)
C9—C10—C11—C120.7 (7)N1—C29—C30—N25.7 (4)
C10—C11—C12—C71.3 (6)C28—C29—C30—N2174.1 (3)
C10—C11—C12—C3178.2 (4)N1—C29—C30—C31173.7 (3)
C6—C7—C12—C11180.0 (4)C28—C29—C30—C316.5 (5)
C8—C7—C12—C110.4 (6)N2—C30—C31—C320.3 (5)
C6—C7—C12—C30.5 (6)C29—C30—C31—C32179.1 (3)
C8—C7—C12—C3179.1 (4)C30—C31—C32—C330.0 (5)
C4—C3—C12—C11179.4 (4)C31—C32—C33—C340.7 (5)
C2—C3—C12—C110.9 (5)C31—C32—C33—C36178.4 (4)
C4—C3—C12—C70.1 (6)C30—N2—C34—C330.8 (5)
C2—C3—C12—C7179.6 (3)Zn1—N2—C34—C33171.8 (3)
Zn1—O4—C13—O36.5 (3)C32—C33—C34—N21.1 (5)
Zn1—O4—C13—C14172.9 (3)C36—C33—C34—N2177.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O10.822.212.948 (3)150
C8—H8A···O4i0.932.593.515 (6)171
Symmetry code: (i) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formula[Zn(C12H9O2)2(C12H12N2)]·0.5H2O
Mr629.00
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)32.212 (7), 8.2668 (17), 25.314 (5)
β (°) 117.865 (4)
V3)5959 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.87
Crystal size (mm)0.30 × 0.28 × 0.21
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.756, 0.819
No. of measured, independent and
observed [I > 2σ(I)] reflections
21468, 5325, 3566
Rint0.049
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.106, 0.99
No. of reflections5325
No. of parameters395
No. of restraints2
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0328P)2 + 11.176P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.45, 0.30

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O10.822.212.948 (3)150
C8—H8A···O4i0.932.593.515 (6)171
Symmetry code: (i) x, y+1, z1/2.
 

Acknowledgements

The authors acknowledge Donghua University for supporting this work.

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGuilera, G. & Steed, J. W. (1999). Chem. Commun. 6, 1294–1296.  Google Scholar
First citationKong, Z. G., Wang, X. Y. & Carlucci, L. (2009). Inorg. Chem. Commun. 12, 691–694  CrossRef CAS Google Scholar
First citationLi, Y.-P., Sun, D.-J., Zang, H., Su, G.-F. & Li, Y.-L. (2009). Acta Cryst. C65, m340–m342.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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