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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 m182
https://doi.org/10.1107/S160053680706610X

Bis[2-(2-amino­ethyl)-1H-benzimidazole-κ2N2,N3]zinc(II) bis­­(perchlorate)

Jine Zhang,a Yanping Li,a Fangjun Huoa and Zhigang Zhanga*

aInstitute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
*Correspondence e-mail: zgzhang@sxu.edu.cn

(Received 20 November 2007; accepted 7 December 2007; online 12 December 2007)

In the title compound, [Zn(C9H11N3)2](ClO4)2, the ZnII atom resides on a crystallographic twofold axis and is coordinated by two benzimidazole N [Zn⋯N = 1.993 (4) Å] and two amine N atoms [Zn⋯N = 2.036 (4) Å] in a distorted tetra­hedral geometry. The crystal packing is dominated by N—H⋯O inter­actions involving the perchlorate anions and π–π stacking inter­actions with an inter­planar separation of 3.42 Å. A weak C—H⋯O inter­action is also present.

Related literature

For related literature, see: Cescon & Day (1961[Cescon, L. A. & Day, A. R. (1961). J. Org. Chem. 27, 581-586.]); Maurva et al. (2006[Maurva, M. R., Kumar, A., Ebel, M. & Rehder, D. (2006). Inorg. Chem. 45, 5924-5937.]); Qiu & Tong (2005[Qiu, X.-H. & Tong, X.-L. (2005). Acta Cryst. E61, m2302-m2304.]); Vallee & Auld (1990[Vallee, B. L. & Auld, D. S. (1990). Biochemistry, 29, 5647-5659.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C9H11N3)2](ClO4)2

  • Mr = 586.69

  • Monoclinic, C 2/c

  • a = 11.150 (3) Å

  • b = 15.343 (4) Å

  • c = 14.156 (4) Å

  • β = 93.322 (4)°

  • V = 2417.7 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.29 mm−1

  • T = 293 (2) K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.698, Tmax = 0.782

  • 5777 measured reflections

  • 2131 independent reflections

  • 1880 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.184

  • S = 1.10

  • 2131 reflections

  • 172 parameters

  • 15 restraints

  • H-atom parameters constrained

  • Δρmax = 0.81 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
N2—H2A⋯O1 0.86 2.09 2.946 (6) 174
N3—H3A⋯O4i 0.90 2.12 2.953 (15) 154
C8—H8A⋯O1ii 0.97 2.42 3.210 (9) 138
Symmetry codes: (i) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) [-x+1, y, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART (Version 5.0), SAINT (Version 6.02) and SHELXTL (Version 6.1). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART (Version 5.0), SAINT (Version 6.02) and SHELXTL (Version 6.1). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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). SMART (Version 5.0), SAINT (Version 6.02) and SHELXTL (Version 6.1). Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680706610X/gg2058sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706610X/gg2058Isup2.hkl

checkCIF report


Comment top

Benzimidazole is of considerable interest as a ligand for transition metal ions. The complexes of transition metal salts with benzimidazole derivatives have been extensively studied as models of some important biological molecules (Maurva et al., 2006). Incorporation of a benzimidazole moiety into alpha-amino acid molecules appeared to be of interest since the benzimidazole group has known biological activity, and its attachment to a carrier group such as an amino acid can facilitate this activity (Cescon & Day, 1961). Zinc complexes may be found in numerous biological systems. They function not only as catalytic centres in enzymes, but also as structural elements supporting three-dimensional protein structures (Vallee & Auld, 1990). In the present paper, we report the synthesis and crystal structure of a new zinc(II) benzimidazole complex, the title compound.

In (I), the Zn(II) ion exhibits a distorted tetrahedral geometry. The coordination sphere of the Zn(II) ion is comprised with two benzimidazole N atoms and two amine N atoms. The Zn—N bond distances (Table 1) are different from those reported in the literature. The Zn—N1 bond distance of 1.993 (4) Å is smaller than that reported in the literature (Qiu & Tong, 2005). The N1—Zn—N3 and N1—Zn—N3A (symmetry code: A -x + 2,y,-z + 1/2) bond angles are 97.02 (16)° and 118.10 (17) °, respectively, indicating a distortion of the tetrahedral coordination.

The ellipsoid plot of the molecule is shown in Fig. 1. The crystal structure of (I) is composed of Bis(1H-2-aminoethylbenzimidazole)zinc(II) cations and perchlorate anions. As illustrated in Fig. 2, intramolecular N—H···O hydrogen bonds and π···π stacking interactions between the benzene ring and imidazole ring [Cg1···Cg2(1/2 - x,1/2 - y,1 - z) = 3.7296 Å; Cg1 is the centroid of atoms N1,C1,C6,N2,C7, Cg2 is the centroid of atoms C1—C6] play key roles in stabilizing the crystal packing. The detailed hydrogen bonds information are listed in Table 2.

Related literature top

For related literature, see: Cescon & Day (1961); Maurva et al. (2006); Qiu & Tong (2005); Sheldrick (1990); Vallee & Auld (1990).

Experimental top

All chemicals were of reagent grade and commercially available from the Beijing Chemical Reagents Company of China, and were used without further purification.

The title compound was prepared by adding a methanol solution (5 ml) of Zn(ClO4)2.6H2O (0.5 mmol) to a methanol solution (10 ml) of 2-aminoethybenzimidazole dihydrochloride (0.5 mmol) (Cescon & Day, 1961) neutralized by potassium carbonate. The mixture was stirred for about four hours and then filtered. Afterwards, the filtrate was slowly evaporated at room temperature to yield colorless crystals of (I) suitable for X-ray analysis. Elemental analyses of the title compound found: C 36.86%, H 3.75%, N 14.33%, and the components of the compound are calculated as C 36.85%, H 3.79%, N 14.30%.

Refinement top

Disorder is present in the perchlorate anion and aminoethyl bridge and was modelled successfully. H atoms were placed in calculated positions and included in the refinement in the riding-model approximation, with C—H distances in the range 0.93–0.97 Å, N—H distances in the range 0.86–0.90 Å and Uiso(H) = 1.2Ueq of the carrier atom.

Structure description top

Benzimidazole is of considerable interest as a ligand for transition metal ions. The complexes of transition metal salts with benzimidazole derivatives have been extensively studied as models of some important biological molecules (Maurva et al., 2006). Incorporation of a benzimidazole moiety into alpha-amino acid molecules appeared to be of interest since the benzimidazole group has known biological activity, and its attachment to a carrier group such as an amino acid can facilitate this activity (Cescon & Day, 1961). Zinc complexes may be found in numerous biological systems. They function not only as catalytic centres in enzymes, but also as structural elements supporting three-dimensional protein structures (Vallee & Auld, 1990). In the present paper, we report the synthesis and crystal structure of a new zinc(II) benzimidazole complex, the title compound.

In (I), the Zn(II) ion exhibits a distorted tetrahedral geometry. The coordination sphere of the Zn(II) ion is comprised with two benzimidazole N atoms and two amine N atoms. The Zn—N bond distances (Table 1) are different from those reported in the literature. The Zn—N1 bond distance of 1.993 (4) Å is smaller than that reported in the literature (Qiu & Tong, 2005). The N1—Zn—N3 and N1—Zn—N3A (symmetry code: A -x + 2,y,-z + 1/2) bond angles are 97.02 (16)° and 118.10 (17) °, respectively, indicating a distortion of the tetrahedral coordination.

The ellipsoid plot of the molecule is shown in Fig. 1. The crystal structure of (I) is composed of Bis(1H-2-aminoethylbenzimidazole)zinc(II) cations and perchlorate anions. As illustrated in Fig. 2, intramolecular N—H···O hydrogen bonds and π···π stacking interactions between the benzene ring and imidazole ring [Cg1···Cg2(1/2 - x,1/2 - y,1 - z) = 3.7296 Å; Cg1 is the centroid of atoms N1,C1,C6,N2,C7, Cg2 is the centroid of atoms C1—C6] play key roles in stabilizing the crystal packing. The detailed hydrogen bonds information are listed in Table 2.

For related literature, see: Cescon & Day (1961); Maurva et al. (2006); Qiu & Tong (2005); Sheldrick (1990); Vallee & Auld (1990).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with 30% displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The packing diagram of (I) with N—H···O hydrogen bonds shown as dashed lines.
Bis[2-(2-aminoethyl)-1H-benzimidazole-κ2N2,N3]zinc(II) bis(perchlorate) top
Crystal data top
[Zn(C9H11N3)2](ClO4)2F(000) = 1200
Mr = 586.69Dx = 1.612 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1957 reflections
a = 11.150 (3) Åθ = 2.3–23.9°
b = 15.343 (4) ŵ = 1.29 mm−1
c = 14.156 (4) ÅT = 293 K
β = 93.322 (4)°Block, colorless
V = 2417.7 (12) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2131 independent reflections
Radiation source: fine-focus sealed tube1880 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.698, Tmax = 0.782k = −18→18
5777 measured reflectionsl = −10→16
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.1191P)2 + 1.6906P]
where P = (Fo2 + 2Fc2)/3
2131 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.81 e Å−3
15 restraintsΔρmin = −0.47 e Å−3
Crystal data top
[Zn(C9H11N3)2](ClO4)2V = 2417.7 (12) Å3
Mr = 586.69Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.150 (3) ŵ = 1.29 mm−1
b = 15.343 (4) ÅT = 293 K
c = 14.156 (4) Å0.30 × 0.20 × 0.20 mm
β = 93.322 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2131 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1880 reflections with I > 2σ(I)
Tmin = 0.698, Tmax = 0.782Rint = 0.023
5777 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06615 restraints
wR(F2) = 0.184H-atom parameters constrained
S = 1.10Δρmax = 0.81 e Å−3
2131 reflectionsΔρmin = −0.47 e Å−3
172 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*/UeqOcc. (<1)
Zn11.00000.13946 (4)0.25000.0506 (3)
N10.8741 (3)0.2124 (2)0.1829 (3)0.0534 (9)
N20.6929 (3)0.2674 (3)0.1500 (3)0.0655 (11)
H2A0.61650.27450.15040.079*
C10.8843 (4)0.2811 (3)0.1191 (3)0.0538 (11)
C20.9833 (5)0.3136 (4)0.0754 (4)0.0712 (14)
H21.05950.29000.08720.085*
C30.9638 (6)0.3819 (4)0.0142 (5)0.0805 (16)
H31.02870.4055−0.01550.097*
C40.8497 (6)0.4174 (4)−0.0050 (4)0.0776 (16)
H40.84130.4643−0.04640.093*
C50.7494 (6)0.3855 (3)0.0351 (4)0.0686 (14)
H50.67320.40830.02110.082*
C60.7700 (4)0.3157 (3)0.0990 (3)0.0549 (11)
C70.7577 (4)0.2068 (3)0.1993 (4)0.0624 (12)
C80.7035 (6)0.1424 (4)0.2624 (5)0.0905 (17)
H8A0.62980.16750.28370.109*0.594 (12)
H8B0.68120.09160.22470.109*0.594 (12)
H8A'0.68760.17280.32050.109*0.406 (12)
H8B'0.62610.12640.23270.109*0.406 (12)
Cl10.37395 (13)0.37873 (10)0.10975 (10)0.0736 (4)
O10.4321 (5)0.2999 (4)0.1393 (6)0.141 (2)
N30.8879 (4)0.0694 (3)0.3295 (3)0.0673 (11)
H3A0.87250.01790.30080.081*0.594 (12)
H3B0.92560.05840.38610.081*0.594 (12)
H3A'0.91790.01520.33720.081*0.406 (12)
H3B'0.88690.09400.38710.081*0.406 (12)
O20.4361 (8)0.4352 (7)0.0603 (7)0.214 (5)
O30.2643 (9)0.3764 (10)0.130 (2)0.235 (14)0.594 (12)
C90.7735 (7)0.1132 (8)0.3445 (6)0.0905 (17)0.594 (12)
H9A0.72430.07350.37900.109*0.594 (12)
H9B0.79040.16330.38490.109*0.594 (12)
O3'0.2863 (12)0.3531 (10)0.0330 (13)0.118 (6)0.406 (12)
C9'0.7639 (7)0.0630 (5)0.2892 (9)0.061 (4)0.406 (12)
H9A'0.76420.02600.23370.073*0.406 (12)
H9B'0.71670.03350.33500.073*0.406 (12)
O40.364 (2)0.4319 (9)0.1837 (10)0.337 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0418 (4)0.0565 (5)0.0526 (5)0.000−0.0053 (3)0.000
N10.0406 (19)0.056 (2)0.063 (2)0.0001 (15)−0.0033 (16)0.0050 (17)
N20.0411 (19)0.069 (2)0.086 (3)0.0064 (18)0.0020 (19)0.003 (2)
C10.050 (2)0.051 (2)0.060 (3)−0.0044 (18)−0.009 (2)−0.004 (2)
C20.057 (3)0.076 (3)0.080 (4)−0.005 (2)−0.002 (3)0.015 (3)
C30.076 (4)0.074 (3)0.092 (4)−0.009 (3)0.005 (3)0.026 (3)
C40.094 (4)0.062 (3)0.075 (4)0.001 (3)−0.010 (3)0.012 (3)
C50.077 (4)0.053 (2)0.074 (3)0.008 (2)−0.019 (3)−0.003 (2)
C60.054 (3)0.047 (2)0.062 (3)0.0038 (19)−0.009 (2)−0.009 (2)
C70.044 (2)0.063 (3)0.080 (3)0.001 (2)−0.001 (2)0.012 (2)
C80.061 (3)0.099 (3)0.113 (4)0.001 (2)0.019 (3)0.030 (3)
Cl10.0667 (9)0.0818 (9)0.0722 (9)0.0043 (6)0.0054 (7)0.0076 (7)
O10.095 (4)0.146 (5)0.182 (6)0.024 (4)0.007 (4)0.039 (4)
N30.064 (2)0.073 (3)0.065 (2)−0.004 (2)0.005 (2)0.014 (2)
O20.172 (7)0.230 (9)0.236 (9)−0.102 (7)−0.023 (7)0.106 (8)
O30.056 (6)0.149 (11)0.51 (4)0.036 (6)0.073 (12)0.136 (18)
C90.061 (3)0.099 (3)0.113 (4)0.001 (2)0.019 (3)0.030 (3)
O3'0.048 (7)0.149 (13)0.152 (14)0.004 (6)−0.036 (7)−0.047 (10)
C9'0.055 (7)0.056 (7)0.072 (8)−0.012 (5)0.009 (6)0.012 (6)
O40.57 (3)0.241 (13)0.207 (10)−0.006 (16)0.084 (15)−0.121 (10)
Geometric parameters (Å, º) top
Zn1—N1i1.993 (4)C8—H8A0.9700
Zn1—N11.993 (4)C8—H8B0.9700
Zn1—N3i2.036 (4)C8—H8A'0.9700
Zn1—N32.036 (4)C8—H8B'0.9700
N1—C71.335 (6)C3—H30.9300
N1—C11.397 (6)Cl1—O31.273 (10)
C5—C41.373 (9)Cl1—O21.333 (7)
C5—C61.412 (7)Cl1—O41.336 (10)
C5—H50.9300Cl1—O11.423 (6)
C1—C21.389 (7)Cl1—O3'1.472 (12)
C1—C61.394 (6)N3—C9'1.468 (8)
C7—N21.347 (6)N3—C91.468 (8)
C7—C81.484 (7)N3—H3A0.9000
C6—N21.372 (6)N3—H3B0.9000
N2—H2A0.8600N3—H3A'0.9000
C2—C31.369 (8)N3—H3B'0.9000
C2—H20.9300C9—H9A0.9700
C4—C31.396 (8)C9—H9B0.9700
C4—H40.9300C9'—H9A'0.9700
C8—C9'1.433 (7)C9'—H9B'0.9700
C8—C91.433 (7)
N1i—Zn1—N1111.6 (2)H8A—C8—H8B'59.1
N1i—Zn1—N3i97.02 (16)H8B—C8—H8B'50.4
N1—Zn1—N3i118.10 (17)H8A'—C8—H8B'106.7
N1i—Zn1—N3118.10 (17)C2—C3—C4122.1 (5)
N1—Zn1—N397.02 (16)C2—C3—H3119.0
N3i—Zn1—N3116.3 (3)C4—C3—H3119.0
C7—N1—C1106.1 (4)O3—Cl1—O2132.2 (7)
C7—N1—Zn1123.1 (3)O3—Cl1—O473.4 (14)
C1—N1—Zn1130.6 (3)O2—Cl1—O494.9 (10)
C4—C5—C6115.4 (5)O3—Cl1—O1109.7 (6)
C4—C5—H5122.3O2—Cl1—O1117.7 (6)
C6—C5—H5122.3O4—Cl1—O1110.3 (9)
C2—C1—C6120.9 (4)O3—Cl1—O3'63.5 (13)
C2—C1—N1130.9 (4)O2—Cl1—O3'97.4 (9)
C6—C1—N1108.2 (4)O4—Cl1—O3'131.1 (11)
N1—C7—N2111.3 (4)O1—Cl1—O3'105.2 (7)
N1—C7—C8125.6 (4)C9'—N3—Zn1114.5 (5)
N2—C7—C8123.1 (4)C9—N3—Zn1113.9 (5)
N2—C6—C1106.2 (4)C9'—N3—H3A67.4
N2—C6—C5131.6 (5)C9—N3—H3A108.8
C1—C6—C5122.2 (5)Zn1—N3—H3A108.8
C7—N2—C6108.2 (4)C9'—N3—H3B135.6
C7—N2—H2A125.9C9—N3—H3B108.8
C6—N2—H2A125.9Zn1—N3—H3B108.8
C3—C2—C1117.1 (5)H3A—N3—H3B107.7
C3—C2—H2121.5C9'—N3—H3A'108.6
C1—C2—H2121.5C9—N3—H3A'136.4
C5—C4—C3122.4 (5)Zn1—N3—H3A'108.6
C5—C4—H4118.8H3A—N3—H3A'45.8
C3—C4—H4118.8H3B—N3—H3A'64.4
C9'—C8—C945.1 (7)C9'—N3—H3B'108.6
C9'—C8—C7121.6 (6)C9—N3—H3B'67.7
C9—C8—C7118.3 (6)Zn1—N3—H3B'108.6
C9'—C8—H8A130.4H3A—N3—H3B'139.9
C9—C8—H8A107.7H3B—N3—H3B'45.6
C7—C8—H8A107.7H3A'—N3—H3B'107.6
C9'—C8—H8B64.1C8—C9—N3117.6 (6)
C9—C8—H8B107.7C8—C9—H9A107.9
C7—C8—H8B107.7N3—C9—H9A107.9
H8A—C8—H8B107.1C8—C9—H9B107.9
C9'—C8—H8A'106.9N3—C9—H9B107.9
C9—C8—H8A'65.3H9A—C9—H9B107.2
C7—C8—H8A'106.9C8—C9'—N3117.6 (6)
H8A—C8—H8A'49.3C8—C9'—H9A'107.9
H8B—C8—H8A'143.1N3—C9'—H9A'107.9
C9'—C8—H8B'106.9C8—C9'—H9B'107.9
C9—C8—H8B'134.5N3—C9'—H9B'107.9
C7—C8—H8B'106.9H9A'—C9'—H9B'107.2
Symmetry code: (i) −x+2, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.862.092.946 (6)174
N3—H3A···O4ii0.902.122.953 (15)154
C8—H8A···O1iii0.972.423.210 (9)138
Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula[Zn(C9H11N3)2](ClO4)2
Mr586.69
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)11.150 (3), 15.343 (4), 14.156 (4)
β (°) 93.322 (4)
V (Å3)2417.7 (12)
Z4
Radiation typeMo Kα
µ (mm−1)1.29
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.698, 0.782
No. of measured, independent and
observed [I > 2σ(I)] reflections		5777, 2131, 1880
Rint0.023
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.184, 1.10
No. of reflections2131
No. of parameters172
No. of restraints15
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.81, −0.47

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.862.092.946 (6)174
N3—H3A···O4i0.902.122.953 (15)154
C8—H8A···O1ii0.972.423.210 (9)138
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1, y, −z+1/2.
 

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 30470408).

References

First citationBruker (2000). SMART (Version 5.0), SAINT (Version 6.02) and SHELXTL (Version 6.1). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCescon, L. A. & Day, A. R. (1961). J. Org. Chem. 27, 581–586.  CrossRef Web of Science Google Scholar
 First citationMaurva, M. R., Kumar, A., Ebel, M. & Rehder, D. (2006). Inorg. Chem. 45, 5924–5937.  Web of Science PubMed Google Scholar
 First citationQiu, X.-H. & Tong, X.-L. (2005). Acta Cryst. E61, m2302–m2304.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1990). Acta Cryst. A46, 467–473.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.  Google Scholar
 First citationVallee, B. L. & Auld, D. S. (1990). Biochemistry, 29, 5647–5659.  CrossRef CAS PubMed Web of Science 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 m182
https://doi.org/10.1107/S160053680706610X
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