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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page m90
https://doi.org/10.1107/S1600536807063155

catena-Poly[[[bis­­(methyl­amine)zinc(II)]-μ-4,4′-oxydibenzoato] N,N-di­methyl­acetamide solvate]

Xianzhu Xu,a* Peng Wanga and Shujie Shia

aSchool of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, People's Republic of China.
*Correspondence e-mail: xianzhuxu@yahoo.com.cn

(Received 18 November 2007; accepted 25 November 2007; online 6 December 2007)

In the title zinc(II) coordination polymer, {[Zn(C14H8O5)(CH5N)2]·C4H9NO}n, each Zn(II) cation is tetra­hedrally coordinated by two carboxyl­ato O atoms of two oba anions (H2oba is 4,4′-oxydibenzoic acid), and two N atoms from two methyl­amine mol­ecules. Each oba anion bridges two Zn(II) cations through the two carboxyl­ate groups in a monodentate fashion, forming one-dimensional polymeric chains. These chains are linked via N–H⋯O hydrogen bonds, forming a two-dimensional supra­molecular network.

Related literature

For related literature, see: Kondo et al. (2004[Kondo, M., Irie, Y., Shimizu, Y., Miyazawa, M., Kawaguchi, H., Nakamura, A., Naito, T., Maeda, K. & Uchida, F. (2004). Inorg. Chem. 43, 6139-6141.]); Luo et al. (2003[Luo, J., Hong, M., Wang, R., Cao, R., Han, L. & Lin, Z. (2003). Eur. J. Inorg. Chem. pp. 2705-2710.]); Sun et al. (2005[Sun, C.-Y., Zheng, X.-J., Song, G., Li, L.-C. & Jin, L.-P. (2005). Eur. J. Inorg. Chem. pp. 4150-4159.]); Yaghi et al. (1998[Yaghi, O. M., Li, H., Davis, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res. 31, 474-484.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C14H8O5)(CH5N)2]·C4H9NO

  • Mr = 470.82

  • Monoclinic, C 2/c

  • a = 27.617 (6) Å

  • b = 8.9276 (18) Å

  • c = 21.212 (4) Å

  • β = 122.46 (3)°

  • V = 4413 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.15 mm−1

  • T = 293 (2) K

  • 0.35 × 0.34 × 0.15 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.690, Tmax = 0.850

  • 20180 measured reflections

  • 4942 independent reflections

  • 2843 reflections with I > 2σ(I)

  • Rint = 0.056
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.149

  • S = 1.04

  • 4942 reflections

  • 276 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1B⋯O4i 0.90 2.21 2.991 (5) 145
N2—H2A⋯O2ii 0.90 2.11 2.966 (4) 159
N2—H2B⋯O6iii 0.90 2.40 3.276 (6) 164
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) -x+2, -y+2, -z+1; (iii) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 2000[Bruker (2000). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063155/fj2083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063155/fj2083Isup2.hkl

checkCIF report


Comment top

Recently, great interest has been focused on the design and synthesis of coordination polymers because of their intriguing network topologies and promising applications (Yaghi et al., 1998). It is well known that the selection of appropriate organic ligands is crucial to the design and synthesis of the supramolecular architectures. In preparing target metal complexes, carboxylate and organic amine ligands have been frequently employed (Luo et al., 2003). More and more interest has focused on long flexible ligands recently, and how to avoid, or make use of, their interpenetration to construct novel coordination polymers is an interesting challenge. 4,4'-oxybis(benzoic acid) (H2oba) ligand, in which two benzene moieties are linked together by a µ2-O bridge, is the typical example of flexible ligand and may offer more possibilities in geometry configuration and coordination modes towards the metal ions. As far as we know, several coordination polymers based on 4,4'-oxybis(benzoic acid) have been obtained (Kondo et al., 2004; Sun et al., 2005). We present here the solvothermal synthesis and crystal structure of title coordination polymer, [Zn(C14H8O5)(CNH5)2.(C4NOH9)]n, (I).

The asymmetric unit of (I) consists of one crystallogaphically independent Zn(II) cation, one oba ligand, two methylamine and one dimethylacetamide molecule. Fig.1 shows the molecular structure of (I) with the atom-labelling scheme. The Zn(II) cation has a slightly distorted tetrahedral coordination geometry and formed by two carboxy oxygen atoms (O1 and O5A) from two oba ligands and two nitrogen atoms (N1 and N2) from two methylamine molecule, with Zn—O distances of 1.949 (3)–1.952 (3) Å and Zn—N distances in the range of 1.996 (4)–2.047 (4) Å. These values are in good agreement with those found in other extended structures (Kondo et al., 2004). The O—Zn—O and N—Zn—N bond angles are 106.28 (11)° and 106.15 (19)°, respectively. The N—Zn—O angles are in the range from 98.65 (12) to 115.75 (14)°. In (I), two carboxylate groups of each oba exhibit bis-monodentate coordination modes, namely oba anion acts as µ2-bridging ligand to connect with two Zn(II) centers and each Zn(II) center connects with two oba anions to form the chain arrangement with Zn···Zn distance of 14.512 (4) Å (Fig. 2). It is found that there are hydrogen bonding interactions between adjacent chains. The N—H···O hydrogen bonds involve the uncoordinated carboxylic oxygen atoms of oba and N—H groups of methylamine molecules from adjacent chains (Table 2). In addition, dimethylacetamide molecules located in the crystal lattice with N—H···O hydrogen bonding interactions involving the oxygen atoms of dimethylacetamide molecules and N—H groups of methylamine molecules (Table 2). Finally, the chains are linked together by hydrogen bonds to form two-dimensional supramolecular network (Fig. 2).

Related literature top

For related literature, see: Kondo et al. (2004); Luo et al. (2003); Sun et al. (2005); Yaghi et al. (1998).

Experimental top

(I) was solvothermally prepared from a mixture of Zn(NO3)2.6H2O (0.044 g, 0.2 mmol), 4,4'-oxybis(benzoic acid) (0.051 g, 0.2 mmol), methylamine (0.05 ml) and dimethylacetamide (10 ml). The slurry was stirred for 30 min and heated at 120 °C for 72 h in a Teflon-lined stainless steel autoclave (25 ml) under autogenous pressure. After cooling to room temperature, the block-shaped crystals were washed with water and dried in air.

Refinement top

The H atoms were placed in geometrical calculated positions, with C—H distances of 0.93–0.96 Å and N—H distances of 0.90 Å. A common displacement parameter was refined for all H atoms.

Structure description top

Recently, great interest has been focused on the design and synthesis of coordination polymers because of their intriguing network topologies and promising applications (Yaghi et al., 1998). It is well known that the selection of appropriate organic ligands is crucial to the design and synthesis of the supramolecular architectures. In preparing target metal complexes, carboxylate and organic amine ligands have been frequently employed (Luo et al., 2003). More and more interest has focused on long flexible ligands recently, and how to avoid, or make use of, their interpenetration to construct novel coordination polymers is an interesting challenge. 4,4'-oxybis(benzoic acid) (H2oba) ligand, in which two benzene moieties are linked together by a µ2-O bridge, is the typical example of flexible ligand and may offer more possibilities in geometry configuration and coordination modes towards the metal ions. As far as we know, several coordination polymers based on 4,4'-oxybis(benzoic acid) have been obtained (Kondo et al., 2004; Sun et al., 2005). We present here the solvothermal synthesis and crystal structure of title coordination polymer, [Zn(C14H8O5)(CNH5)2.(C4NOH9)]n, (I).

The asymmetric unit of (I) consists of one crystallogaphically independent Zn(II) cation, one oba ligand, two methylamine and one dimethylacetamide molecule. Fig.1 shows the molecular structure of (I) with the atom-labelling scheme. The Zn(II) cation has a slightly distorted tetrahedral coordination geometry and formed by two carboxy oxygen atoms (O1 and O5A) from two oba ligands and two nitrogen atoms (N1 and N2) from two methylamine molecule, with Zn—O distances of 1.949 (3)–1.952 (3) Å and Zn—N distances in the range of 1.996 (4)–2.047 (4) Å. These values are in good agreement with those found in other extended structures (Kondo et al., 2004). The O—Zn—O and N—Zn—N bond angles are 106.28 (11)° and 106.15 (19)°, respectively. The N—Zn—O angles are in the range from 98.65 (12) to 115.75 (14)°. In (I), two carboxylate groups of each oba exhibit bis-monodentate coordination modes, namely oba anion acts as µ2-bridging ligand to connect with two Zn(II) centers and each Zn(II) center connects with two oba anions to form the chain arrangement with Zn···Zn distance of 14.512 (4) Å (Fig. 2). It is found that there are hydrogen bonding interactions between adjacent chains. The N—H···O hydrogen bonds involve the uncoordinated carboxylic oxygen atoms of oba and N—H groups of methylamine molecules from adjacent chains (Table 2). In addition, dimethylacetamide molecules located in the crystal lattice with N—H···O hydrogen bonding interactions involving the oxygen atoms of dimethylacetamide molecules and N—H groups of methylamine molecules (Table 2). Finally, the chains are linked together by hydrogen bonds to form two-dimensional supramolecular network (Fig. 2).

For related literature, see: Kondo et al. (2004); Luo et al. (2003); Sun et al. (2005); Yaghi et al. (1998).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A perspective view of molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as spheres of arbitrary radii. [symmetry code: (A) x + 1/2,y - 1/2,z.].
[Figure 2] Fig. 2. A packing diagram of (I). The dashed lines indicate the hydrogen bonds.
catena-Poly[[[bis(methylamine)zinc(II)]-µ-4,4'-oxydibenzoato] N,N-dimethylacetamide] top
Crystal data top
[Zn(C14H8O5)(CH5N)2]·C4H9NOF(000) = 1968
Mr = 470.82Dx = 1.417 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 11100 reflections
a = 27.617 (6) Åθ = 3.0–27.5°
b = 8.9276 (18) ŵ = 1.15 mm−1
c = 21.212 (4) ÅT = 293 K
β = 122.46 (3)°Block, colorless
V = 4413 (2) Å30.35 × 0.34 × 0.15 mm
Z = 8
Data collection top
Rigaku RAXIS-RAPID
diffractometer		4942 independent reflections
Radiation source: fine-focus sealed tube2843 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scanh = −34→35
Absorption correction: multi-scan
(Higashi, 1995)		k = −11→11
Tmin = 0.690, Tmax = 0.850l = −27→27
20180 measured reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.065P)2 + 3.5742P]
where P = (Fo2 + 2Fc2)/3
4942 reflections(Δ/σ)max = 0.016
276 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.47 e Å−3
Crystal data top
[Zn(C14H8O5)(CH5N)2]·C4H9NOV = 4413 (2) Å3
Mr = 470.82Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.617 (6) ŵ = 1.15 mm−1
b = 8.9276 (18) ÅT = 293 K
c = 21.212 (4) Å0.35 × 0.34 × 0.15 mm
β = 122.46 (3)°
Data collection top
Rigaku RAXIS-RAPID
diffractometer		4942 independent reflections
Absorption correction: multi-scan
(Higashi, 1995)		2843 reflections with I > 2σ(I)
Tmin = 0.690, Tmax = 0.850Rint = 0.056
20180 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.04Δρmax = 0.43 e Å−3
4942 reflectionsΔρmin = −0.47 e Å−3
276 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.

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
xyzUiso*/Ueq
Zn11.006041 (17)0.74836 (5)0.42522 (2)0.05793 (17)
O10.92334 (11)0.7166 (3)0.37118 (16)0.0679 (7)
O20.92687 (11)0.9063 (3)0.44038 (16)0.0727 (8)
O30.66245 (11)0.7259 (3)0.26587 (18)0.0794 (9)
O40.53662 (14)0.9180 (4)0.43119 (19)0.0892 (10)
O50.53394 (11)1.1281 (3)0.37427 (16)0.0699 (7)
O60.6660 (2)0.4181 (4)0.4624 (3)0.1244 (15)
N11.04661 (18)0.7142 (7)0.5352 (2)0.1189 (18)
H1A1.04130.79670.55520.143*
H1B1.02840.63870.54220.143*
N21.03183 (15)0.9546 (4)0.4121 (2)0.0781 (11)
H2A1.03741.01440.44970.094*
H2B1.06570.94470.41590.094*
N30.7274 (2)0.3980 (5)0.4262 (3)0.1002 (14)
C10.90007 (16)0.8060 (4)0.3942 (2)0.0561 (9)
C20.83754 (14)0.7855 (4)0.3618 (2)0.0489 (8)
C30.80568 (15)0.6814 (4)0.3053 (2)0.0563 (9)
H30.82410.62280.28810.068*
C40.74798 (15)0.6634 (4)0.2745 (2)0.0588 (9)
H40.72750.59350.23670.071*
C50.72034 (15)0.7500 (4)0.3001 (2)0.0550 (9)
C60.75117 (15)0.8530 (4)0.3565 (2)0.0581 (9)
H60.73280.91030.37410.070*
C70.80910 (15)0.8709 (4)0.3866 (2)0.0538 (9)
H70.82940.94140.42410.065*
C80.63392 (16)0.7940 (5)0.2969 (2)0.0612 (10)
C90.63948 (19)0.7328 (4)0.3591 (3)0.0736 (12)
H90.66310.65010.38170.088*
C100.60983 (17)0.7938 (4)0.3885 (2)0.0660 (11)
H100.61260.75050.43020.079*
C110.57618 (14)0.9188 (4)0.3560 (2)0.0532 (9)
C120.57183 (15)0.9781 (4)0.2931 (2)0.0578 (9)
H120.54931.06270.27100.069*
C130.60007 (15)0.9151 (4)0.2624 (2)0.0615 (10)
H130.59610.95430.21920.074*
C140.54638 (16)0.9909 (5)0.3901 (2)0.0618 (10)
C151.1043 (2)0.6820 (8)0.5769 (3)0.1136 (18)
H15A1.10970.57590.57650.170*
H15B1.12030.71510.62740.170*
H15C1.12310.73250.55590.170*
C160.9915 (2)1.0269 (6)0.3416 (3)0.1081 (17)
H16A0.98650.96620.30120.162*
H16B1.00611.12340.33990.162*
H16C0.95531.03880.33720.162*
C170.7729 (4)0.4772 (9)0.4917 (4)0.176 (3)
H17A0.77560.57800.47810.264*
H17B0.80880.42680.51020.264*
H17C0.76420.47900.52980.264*
C180.7438 (3)0.3428 (8)0.3747 (4)0.135 (2)
H18A0.76270.24770.39200.202*
H18B0.76940.41320.37310.202*
H18C0.71010.33150.32560.202*
C190.6771 (3)0.3747 (5)0.4157 (4)0.0996 (17)
C200.6342 (3)0.3043 (9)0.3452 (5)0.155 (3)
H20A0.63800.19730.35020.233*
H20B0.63980.33630.30640.233*
H20C0.59650.33290.33260.233*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0438 (3)0.0778 (3)0.0601 (3)0.00039 (19)0.0331 (2)−0.0105 (2)
O10.0482 (14)0.0878 (19)0.0793 (19)−0.0015 (12)0.0420 (14)−0.0218 (14)
O20.0553 (16)0.092 (2)0.077 (2)−0.0088 (14)0.0396 (15)−0.0233 (16)
O30.0444 (15)0.107 (2)0.092 (2)−0.0008 (13)0.0398 (15)−0.0396 (17)
O40.094 (2)0.116 (2)0.095 (2)−0.0078 (19)0.076 (2)−0.0023 (19)
O50.0635 (17)0.086 (2)0.078 (2)0.0096 (14)0.0498 (15)−0.0068 (15)
O60.172 (4)0.111 (3)0.147 (4)0.017 (3)0.123 (4)0.000 (3)
N10.062 (3)0.237 (6)0.069 (3)0.002 (3)0.043 (2)0.012 (3)
N20.069 (2)0.094 (3)0.084 (3)−0.0183 (19)0.049 (2)−0.030 (2)
N30.104 (4)0.096 (3)0.117 (4)0.025 (3)0.070 (3)0.018 (3)
C10.048 (2)0.069 (2)0.060 (2)0.0024 (18)0.0350 (19)−0.0031 (19)
C20.0444 (19)0.061 (2)0.049 (2)0.0049 (14)0.0307 (17)0.0014 (15)
C30.047 (2)0.069 (2)0.060 (2)0.0050 (17)0.0333 (19)−0.0123 (19)
C40.047 (2)0.076 (2)0.058 (2)0.0005 (17)0.0308 (18)−0.0182 (19)
C50.0406 (18)0.066 (2)0.064 (2)0.0024 (16)0.0320 (17)−0.0103 (19)
C60.052 (2)0.063 (2)0.074 (3)0.0047 (17)0.044 (2)−0.0121 (19)
C70.049 (2)0.060 (2)0.059 (2)0.0008 (15)0.0335 (18)−0.0095 (17)
C80.042 (2)0.078 (2)0.071 (3)−0.0061 (17)0.0349 (19)−0.020 (2)
C90.063 (3)0.064 (2)0.099 (4)0.0134 (19)0.046 (3)0.000 (2)
C100.060 (2)0.071 (2)0.076 (3)−0.0045 (19)0.042 (2)0.005 (2)
C110.0364 (18)0.067 (2)0.063 (2)−0.0029 (15)0.0306 (17)−0.0053 (18)
C120.0427 (19)0.070 (2)0.064 (2)0.0070 (16)0.0313 (18)0.0011 (19)
C130.045 (2)0.085 (3)0.064 (2)0.0033 (18)0.0356 (19)−0.005 (2)
C140.044 (2)0.088 (3)0.064 (3)−0.0047 (19)0.0354 (19)−0.009 (2)
C150.080 (4)0.155 (5)0.082 (4)0.006 (4)0.028 (3)0.022 (4)
C160.105 (4)0.109 (4)0.104 (4)−0.023 (3)0.052 (4)0.005 (3)
C170.157 (7)0.146 (6)0.115 (6)−0.024 (6)0.000 (5)−0.023 (5)
C180.159 (6)0.149 (6)0.153 (6)0.025 (5)0.121 (6)0.012 (5)
C190.126 (5)0.068 (3)0.117 (5)0.005 (3)0.073 (4)0.005 (3)
C200.125 (6)0.154 (6)0.180 (8)−0.054 (5)0.077 (6)−0.062 (6)
Geometric parameters (Å, º) top
Zn1—O11.949 (3)C6—H60.9300
Zn1—O5i1.952 (3)C7—H70.9300
Zn1—N11.996 (4)C8—C91.358 (6)
Zn1—N22.047 (4)C8—C131.358 (5)
O1—C11.275 (4)C9—C101.380 (6)
O2—C11.238 (4)C9—H90.9300
O3—C51.372 (4)C10—C111.377 (5)
O3—C81.407 (4)C10—H100.9300
O4—C141.228 (5)C11—C121.379 (5)
O5—C141.267 (5)C11—C141.501 (5)
O5—Zn1ii1.952 (3)C12—C131.378 (5)
O6—C191.246 (6)C12—H120.9300
N1—C151.374 (7)C13—H130.9300
N1—H1A0.9000C15—H15A0.9600
N1—H1B0.9000C15—H15B0.9600
N2—C161.450 (6)C15—H15C0.9600
N2—H2A0.9000C16—H16A0.9600
N2—H2B0.9000C16—H16B0.9600
N3—C191.302 (7)C16—H16C0.9600
N3—C171.462 (8)C17—H17A0.9600
N3—C181.472 (7)C17—H17B0.9600
C1—C21.488 (5)C17—H17C0.9600
C2—C71.386 (4)C18—H18A0.9600
C2—C31.393 (5)C18—H18B0.9600
C3—C41.369 (5)C18—H18C0.9600
C3—H30.9300C19—C201.460 (9)
C4—C51.386 (5)C20—H20A0.9600
C4—H40.9300C20—H20B0.9600
C5—C61.380 (5)C20—H20C0.9600
C6—C71.377 (5)
O1—Zn1—O5i106.28 (11)C10—C9—H9120.2
O1—Zn1—N1114.24 (15)C11—C10—C9119.9 (4)
O5i—Zn1—N1114.99 (17)C11—C10—H10120.1
O1—Zn1—N2115.75 (14)C9—C10—H10120.1
O5i—Zn1—N298.65 (12)C10—C11—C12118.7 (3)
N1—Zn1—N2106.15 (19)C10—C11—C14120.2 (4)
C1—O1—Zn1110.9 (2)C12—C11—C14121.0 (3)
C5—O3—C8118.1 (3)C13—C12—C11121.6 (4)
C14—O5—Zn1ii121.1 (3)C13—C12—H12119.2
C15—N1—Zn1120.9 (3)C11—C12—H12119.2
C15—N1—H1A107.1C8—C13—C12118.0 (4)
Zn1—N1—H1A107.1C8—C13—H13121.0
C15—N1—H1B107.1C12—C13—H13121.0
Zn1—N1—H1B107.1O4—C14—O5124.7 (4)
H1A—N1—H1B106.8O4—C14—C11120.0 (4)
C16—N2—Zn1114.2 (3)O5—C14—C11115.3 (4)
C16—N2—H2A108.7N1—C15—H15A109.5
Zn1—N2—H2A108.7N1—C15—H15B109.5
C16—N2—H2B108.7H15A—C15—H15B109.5
Zn1—N2—H2B108.7N1—C15—H15C109.5
H2A—N2—H2B107.6H15A—C15—H15C109.5
C19—N3—C17122.3 (6)H15B—C15—H15C109.5
C19—N3—C18123.1 (6)N2—C16—H16A109.5
C17—N3—C18114.7 (6)N2—C16—H16B109.5
O2—C1—O1123.1 (3)H16A—C16—H16B109.5
O2—C1—C2120.5 (3)N2—C16—H16C109.5
O1—C1—C2116.4 (3)H16A—C16—H16C109.5
C7—C2—C3117.9 (3)H16B—C16—H16C109.5
C7—C2—C1120.7 (3)N3—C17—H17A109.5
C3—C2—C1121.3 (3)N3—C17—H17B109.5
C4—C3—C2121.7 (3)H17A—C17—H17B109.5
C4—C3—H3119.2N3—C17—H17C109.5
C2—C3—H3119.2H17A—C17—H17C109.5
C3—C4—C5119.5 (3)H17B—C17—H17C109.5
C3—C4—H4120.3N3—C18—H18A109.5
C5—C4—H4120.3N3—C18—H18B109.5
O3—C5—C6124.4 (3)H18A—C18—H18B109.5
O3—C5—C4115.8 (3)N3—C18—H18C109.5
C6—C5—C4119.8 (3)H18A—C18—H18C109.5
C7—C6—C5120.2 (3)H18B—C18—H18C109.5
C7—C6—H6119.9O6—C19—N3120.7 (6)
C5—C6—H6119.9O6—C19—C20122.5 (7)
C6—C7—C2120.9 (3)N3—C19—C20116.7 (6)
C6—C7—H7119.5C19—C20—H20A109.5
C2—C7—H7119.5C19—C20—H20B109.5
C9—C8—C13122.1 (4)H20A—C20—H20B109.5
C9—C8—O3118.7 (4)C19—C20—H20C109.5
C13—C8—O3119.2 (4)H20A—C20—H20C109.5
C8—C9—C10119.7 (4)H20B—C20—H20C109.5
C8—C9—H9120.2
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O4iii0.902.212.991 (5)145
N2—H2A···O2iv0.902.112.966 (4)159
N2—H2B···O6v0.902.403.276 (6)164
Symmetry codes: (iii) −x+3/2, −y+3/2, −z+1; (iv) −x+2, −y+2, −z+1; (v) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Zn(C14H8O5)(CH5N)2]·C4H9NO
Mr470.82
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)27.617 (6), 8.9276 (18), 21.212 (4)
β (°) 122.46 (3)
V (Å3)4413 (2)
Z8
Radiation typeMo Kα
µ (mm−1)1.15
Crystal size (mm)0.35 × 0.34 × 0.15
Data collection
DiffractometerRigaku RAXIS-RAPID
Absorption correctionMulti-scan
(Higashi, 1995)
Tmin, Tmax0.690, 0.850
No. of measured, independent and
observed [I > 2σ(I)] reflections		20180, 4942, 2843
Rint0.056
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.149, 1.04
No. of reflections4942
No. of parameters276
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.43, −0.47

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O4i0.902.212.991 (5)145
N2—H2A···O2ii0.902.112.966 (4)159
N2—H2B···O6iii0.902.403.276 (6)164
Symmetry codes: (i) −x+3/2, −y+3/2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x+1/2, y+1/2, z.
 

Acknowledgements

This work was supported by the National Science Foundation of China (50678045), the Science Foundation of Heilongjiang Province (E200519), the China Postdoctoral Science Foundation and Heilongjiang Postdoctoral Financial Assistance.

References

First citationBruker (2000). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationKondo, M., Irie, Y., Shimizu, Y., Miyazawa, M., Kawaguchi, H., Nakamura, A., Naito, T., Maeda, K. & Uchida, F. (2004). Inorg. Chem. 43, 6139–6141.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationLuo, J., Hong, M., Wang, R., Cao, R., Han, L. & Lin, Z. (2003). Eur. J. Inorg. Chem. pp. 2705–2710.  Web of Science CSD CrossRef Google Scholar
 First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.  Google Scholar
 First citationSun, C.-Y., Zheng, X.-J., Song, G., Li, L.-C. & Jin, L.-P. (2005). Eur. J. Inorg. Chem. pp. 4150–4159.  Web of Science CSD CrossRef Google Scholar
 First citationYaghi, O. M., Li, H., Davis, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res. 31, 474–484.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page m90
https://doi.org/10.1107/S1600536807063155
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