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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 66| Part 11| November 2010| Page m1404
https://doi.org/10.1107/S160053681003970X

catena-Poly[[[tetra­aqua­zinc(II)]-μ-1,4-bis­­(1,2,4-triazol-1-yl)butane-κ2N4:N4′] bi­phenyl-4,4′-di­carboxyl­ate]

Chang-Mei Jiaoa*

aDepartment of Chemistry, Yancheng Teachers' College, Yancheng 224002, People's Republic of China
*Correspondence e-mail: wjndyc@gmail.com

(Received 25 September 2010; accepted 4 October 2010; online 13 October 2010)

The asymmetric unit of the polymeric title compound, {[Zn(C8H12N6)(H2O)4](C14H8O4)}n or {[Zn(BTB)(H2O)4](BPDC)}n [BTB is 1,4-bis­(1,2,4-triazol-1-yl)butane and H2BPDC is biphenyl-4,4′-dicarb­oxy­lic acid], contains half a [Zn(BTB)(H2O)4]2+ cation and half a BPDC anion, both ions lying about a crystallographic inversion centre. The crystal structure consists of zigzag polymeric cationic chains parallel to the c axis and uncoordinated anions linked into a three-dimensional supra­molecular architecture by O—H⋯O, C—H⋯O hydrogen bonds and C—H⋯π inter­actions.

Related literature

For general background to the structures and applications of supra­molecular compounds, see: Kitagawa et al. (2004[Kitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334-2375.]); Ferey et al. (2005[Ferey, G., Mellot-Draznieks, C., Serre, C. & Millange, F. (2005). Acc. Chem. Res. 38, 217-225.]); Roy et al. (2009[Roy, S., Mahata, G. & Biradha, K. (2009). Cryst. Growth Des. 9, 5006-5008.]); Zhang et al. (2009[Zhang, Y. B., Zhang, W. X., Feng, F. Y., Zhang, J. P. & Chen, X. M. (2009). Angew. Chem. Int. Ed. 48, 5287-5290.]). For related compounds based on 1,4-bis­(1,2,4-triazol-1-yl)butane, see: Liu et al. (2008[Liu, X., Liu, K., Yang, Y. & Li, B. (2008). Inorg. Chem. Commun. 11, 1273-1275.]); Gu et al. (2008[Gu, Z.-G., Xu, Y.-F., Zhou, X.-H., Zuo, J.-L. & You, X.-Z. (2008). Cryst. Growth Des. 8, 1306-1312.]); Wang et al. (2008[Wang, L.-Y., Yang, Y., Liu, K., Li, B.-L. & Zhang, Y. (2008). Cryst. Growth Des. 8, 3902-3904.]); Zhu et al. (2009[Zhu, X., Liu, X.-G., Li, B.-L. & Zhang, Y. (2009). CrystEngComm, 11, 997-1000.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C8H12N6)(H2O)4](C14H8O4)

  • Mr = 569.89

  • Triclinic, [P \overline 1]

  • a = 6.4344 (15) Å

  • b = 7.1490 (18) Å

  • c = 13.539 (3) Å

  • α = 89.250 (4)°

  • β = 81.348 (4)°

  • γ = 72.620 (3)°

  • V = 587.3 (2) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.11 mm−1

  • T = 293 K

  • 0.21 × 0.19 × 0.17 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.792, Tmax = 0.828

  • 3162 measured reflections

  • 2299 independent reflections

  • 1788 reflections with I > 2σ(I)

  • Rint = 0.032
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.080

  • S = 0.92

  • 2237 reflections

  • 169 parameters

  • H-atom parameters constrained

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C6–C11 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2A⋯O4i 0.93 2.50 3.342 (3) 150
O1—H1D⋯O3ii 0.85 2.07 2.825 (3) 148
O1—H1C⋯O3 0.85 1.95 2.783 (2) 167
O2—H2C⋯O4iii 0.85 1.85 2.642 (3) 155
O2—H2D⋯O3 0.85 2.06 2.839 (3) 151
C3—H3B⋯Cg 0.97 2.82 3.552 (3) 133
Symmetry codes: (i) x+1, y-1, z; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681003970X/rz2494sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003970X/rz2494Isup2.hkl

checkCIF report


Comment top

Interest in crystal engineering and supramolecular chemistry is rapidly increasing not only because of their fascinating structures and topologies but also owing to their potential use in optical, electrical, catalytic and adsorptive applications (Kitagawa et al., 2004; Ferey et al., 2005; Roy et al., 2009; Zhang et al., 2009). The construction of such coordination polymers is highly influenced by several factors. However, the key factor in the manipulating coordination polymers is undoubtedly the selection of appropriate ligands. Comparing to rigid ligands, bifunctional flexible ligands can induce variability of the structure and may lead to the formation of supramolecular isomers because of their conformational flexibility. Recently, a series of transition metal coordination polymers based on the flexible ligand 1,4-bis(1,2,4-triazol-1-yl)butane have been reported (Liu et al., 2008; Gu et al., 2008; Wang et al., 2008; Zhu et al., 2009). In this paper, biphenyl-4,4'-dicarboxylic acid (H2BPDC) and 1,4-bis(1,2,4-triazol-1-yl)butane (BTB) have been selected as organic linkers, generating the title new zinc(II) coordination polymer, (I), the crystal structure of which is reported herein.

Compound (I) crystallizes in the triclinic space group P -1, and the asymmetric unit contains half a [Zn(C8H12N6)(H2O)4]2+ cation and half a uncoordinated BPDC anion. Each zinc(II) metal is located on an inversion centre and is six-coordinated in a octahedron geometry by two triazole nitrogen atoms from two different BTB ligand in the axial positions, and four oxygen atom from coordinated water molecules at the equatorial plane (Figure 1). The Zn–N bond length is 2.096 (2) Å, while the Zn–O bond lengths are 2.1234 (18) Å, 2.1693 (19)Å respectively. The BTB ligand adopts a trans–trans-trans conformation and acts as a N,N'-bidentate ligand linking centrosymmetrically-related zinc(II) cations into one-dimensional zig-zag cationic chains parallel to the c axis. The doubly deprotonated BPDC anion, which has crystallographically imposed centre of symmetry, does not coordinate to the zinc(II) centres and only acts as counter-ion. The anionic and cationic parts of (I) interact to form a three-dimensional network through intermolecular interactions such as conventional O—H···O hydrogen bonds, non-conventional C—H···O contacts and C—H···π interactions (Table 1). The C—H···π interaction is observed between the H3B atom and the centroid of the C6–C11 ring. As shown in Figure 2, interchain O1—H1C···O3, O1—H1D···O3, O2—H2D···O3 bonds between coordinated water molecules and the carboxylate anion are found to assemble the 1-D motifs into a 2-D layer parallel to the bc plane. These layers are further connected by interlayer O2—H2C···O4, C2—H2A···O4 hydrogen bonds, forming a 3-D supramolecular network (Figure 3).

Related literature top

For general background to the structures and applications of supramolecular compounds, see: Kitagawa et al. (2004); Ferey et al. (2005); Roy et al. (2009); Zhang et al. (2009). For related compounds based on 1,4-bis(1,2,4-triazol-1-yl)butane, see: Li et al. (2006); Liu et al. (2008); Gu et al. (2008); Wang et al. (2008); Zhu et al. (2009).

Experimental top

A mixture of Zn(NO3)2.6H2O (29.7 mg, 0.1 mmol), biphenyl-4,4'-dicarboxylic acid (H2BPDC) (24.2 mg, 0.1 mmol), 1,4-bis(1,2,4-triazol-1-yl)butane (BTB) (19.2 mg, 0.1 mmol), and KOH (11.2 mg, 0.2 mmol) in H2O (10 ml) was sealed in a 16 ml Teflon-lined stainless steel container and heated at 180°C for 72 h. After cooling to room temperature, white block crystals of the title compound were collected by filtration and washed with water and ethanol several times (yield 51.3%, based on H2BPDC). Elemental analysis for C22H28ZnN6O8 (Mr = 569.87): C 46.37, H 4.95, N 14.75%; found: 46.46, H 4.98, N 14.79%.

Refinement top

The water H atoms were located in a difference Fourier map and fixed in the refinement, with Uiso(H)=1.2Ueq(O). All C-bound H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93 (triazole, aromatic) or 0.97 Å(methylene) and Uiso(H) = 1.2Ueq(C).

Structure description top

Interest in crystal engineering and supramolecular chemistry is rapidly increasing not only because of their fascinating structures and topologies but also owing to their potential use in optical, electrical, catalytic and adsorptive applications (Kitagawa et al., 2004; Ferey et al., 2005; Roy et al., 2009; Zhang et al., 2009). The construction of such coordination polymers is highly influenced by several factors. However, the key factor in the manipulating coordination polymers is undoubtedly the selection of appropriate ligands. Comparing to rigid ligands, bifunctional flexible ligands can induce variability of the structure and may lead to the formation of supramolecular isomers because of their conformational flexibility. Recently, a series of transition metal coordination polymers based on the flexible ligand 1,4-bis(1,2,4-triazol-1-yl)butane have been reported (Liu et al., 2008; Gu et al., 2008; Wang et al., 2008; Zhu et al., 2009). In this paper, biphenyl-4,4'-dicarboxylic acid (H2BPDC) and 1,4-bis(1,2,4-triazol-1-yl)butane (BTB) have been selected as organic linkers, generating the title new zinc(II) coordination polymer, (I), the crystal structure of which is reported herein.

Compound (I) crystallizes in the triclinic space group P -1, and the asymmetric unit contains half a [Zn(C8H12N6)(H2O)4]2+ cation and half a uncoordinated BPDC anion. Each zinc(II) metal is located on an inversion centre and is six-coordinated in a octahedron geometry by two triazole nitrogen atoms from two different BTB ligand in the axial positions, and four oxygen atom from coordinated water molecules at the equatorial plane (Figure 1). The Zn–N bond length is 2.096 (2) Å, while the Zn–O bond lengths are 2.1234 (18) Å, 2.1693 (19)Å respectively. The BTB ligand adopts a trans–trans-trans conformation and acts as a N,N'-bidentate ligand linking centrosymmetrically-related zinc(II) cations into one-dimensional zig-zag cationic chains parallel to the c axis. The doubly deprotonated BPDC anion, which has crystallographically imposed centre of symmetry, does not coordinate to the zinc(II) centres and only acts as counter-ion. The anionic and cationic parts of (I) interact to form a three-dimensional network through intermolecular interactions such as conventional O—H···O hydrogen bonds, non-conventional C—H···O contacts and C—H···π interactions (Table 1). The C—H···π interaction is observed between the H3B atom and the centroid of the C6–C11 ring. As shown in Figure 2, interchain O1—H1C···O3, O1—H1D···O3, O2—H2D···O3 bonds between coordinated water molecules and the carboxylate anion are found to assemble the 1-D motifs into a 2-D layer parallel to the bc plane. These layers are further connected by interlayer O2—H2C···O4, C2—H2A···O4 hydrogen bonds, forming a 3-D supramolecular network (Figure 3).

For general background to the structures and applications of supramolecular compounds, see: Kitagawa et al. (2004); Ferey et al. (2005); Roy et al. (2009); Zhang et al. (2009). For related compounds based on 1,4-bis(1,2,4-triazol-1-yl)butane, see: Li et al. (2006); Liu et al. (2008); Gu et al. (2008); Wang et al. (2008); Zhu et al. (2009).

Computing details top

Data collection: SMART (Bruker 2000); cell refinement: SAINT (Bruker 2000); data reduction: SAINT (Bruker 2000); program(s) used to solve structure: SHELXS97 (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
[Figure 1] Fig. 1. A view of the structure of the title compound, showing the atom-numbering scheme and the coordination geometry around the zinc(II) centre. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (A) 1-x, 1-y, 1-z; (B) 1-x, -y, -z; (C) 1-x, -y, 1-z]
[Figure 2] Fig. 2. A perspective view of the two-dimensional supramolecular sheet of the title compound along the a axis, showing intermolecular O—H···O hydrogen bonds and C—H···π interactions (dashed lines).
[Figure 3] Fig. 3. The three-dimensional network of the title compound. Dashed lines indicate hydrogen bonds.
catena-Poly[[[tetraaquazinc(II)]-µ-1,4-bis(1,2,4-triazol-1-yl)butane- κ2N4:N4'] biphenyl-4,4'-dicarboxylate] top
Crystal data top
[Zn(C8H12N6)(H2O)4](C14H8O4)Z = 1
Mr = 569.89F(000) = 296
Triclinic, P1Dx = 1.611 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4344 (15) ÅCell parameters from 1152 reflections
b = 7.1490 (18) Åθ = 3.0–25.0°
c = 13.539 (3) ŵ = 1.11 mm−1
α = 89.250 (4)°T = 293 K
β = 81.348 (4)°Block, white
γ = 72.620 (3)°0.21 × 0.19 × 0.17 mm
V = 587.3 (2) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		2299 independent reflections
Radiation source: fine-focus sealed tube1788 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
phi and ω scansθmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −6→7
Tmin = 0.792, Tmax = 0.828k = −6→8
3162 measured reflectionsl = −16→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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0317P)2]
where P = (Fo2 + 2Fc2)/3
2237 reflections(Δ/σ)max < 0.001
169 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
[Zn(C8H12N6)(H2O)4](C14H8O4)γ = 72.620 (3)°
Mr = 569.89V = 587.3 (2) Å3
Triclinic, P1Z = 1
a = 6.4344 (15) ÅMo Kα radiation
b = 7.1490 (18) ŵ = 1.11 mm−1
c = 13.539 (3) ÅT = 293 K
α = 89.250 (4)°0.21 × 0.19 × 0.17 mm
β = 81.348 (4)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2299 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1788 reflections with I > 2σ(I)
Tmin = 0.792, Tmax = 0.828Rint = 0.032
3162 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 0.92Δρmax = 0.47 e Å−3
2237 reflectionsΔρmin = −0.31 e Å−3
169 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
C10.1236 (5)0.0898 (4)0.1819 (2)0.0408 (7)
H1A0.01800.11810.13950.049*
C20.4301 (4)−0.0006 (4)0.23078 (18)0.0323 (6)
H2A0.5802−0.04730.23370.039*
C30.2822 (4)0.0747 (4)0.41485 (17)0.0347 (7)
H3A0.18350.01010.45190.042*
H3B0.22820.21250.43500.042*
C40.5070 (4)−0.0100 (4)0.44352 (17)0.0311 (6)
H4A0.60590.05840.41030.037*
H4B0.5653−0.14730.42240.037*
C50.1402 (5)0.5973 (4)0.18630 (19)0.0319 (6)
C60.2502 (4)0.5703 (4)0.27840 (17)0.0275 (6)
C70.1272 (4)0.6255 (4)0.37179 (19)0.0375 (7)
H7−0.02450.68250.37730.045*
C80.2241 (4)0.5981 (4)0.45708 (19)0.0367 (7)
H80.13580.63660.51870.044*
C90.4489 (4)0.5149 (3)0.45388 (17)0.0262 (6)
C100.5721 (4)0.4649 (4)0.35941 (19)0.0389 (7)
H100.72430.41200.35340.047*
C110.4747 (5)0.4915 (4)0.27460 (19)0.0393 (7)
H110.56290.45520.21280.047*
N10.3416 (3)0.0186 (3)0.14818 (15)0.0333 (6)
N20.0731 (4)0.1156 (3)0.27853 (16)0.0416 (6)
N30.2730 (4)0.0566 (3)0.30894 (15)0.0299 (5)
O10.6429 (3)0.2192 (3)0.04395 (12)0.0405 (5)
H1C0.53830.31920.06810.049*
H1D0.71030.2541−0.00850.049*
O20.2224 (3)0.2334 (3)−0.02699 (13)0.0459 (5)
H2C0.20930.2385−0.08860.055*
H2D0.22840.3433−0.00650.055*
O30.2593 (3)0.5246 (3)0.10408 (13)0.0407 (5)
O4−0.0583 (3)0.6896 (3)0.19568 (13)0.0484 (6)
Zn10.50000.00000.00000.03341 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0328 (18)0.0533 (19)0.0323 (16)−0.0054 (14)−0.0083 (13)0.0027 (13)
C20.0283 (15)0.0366 (16)0.0266 (14)−0.0028 (13)−0.0014 (12)0.0002 (12)
C30.0380 (17)0.0397 (16)0.0211 (14)−0.0057 (13)0.0000 (12)−0.0039 (12)
C40.0349 (16)0.0298 (15)0.0243 (14)−0.0051 (12)−0.0007 (12)−0.0001 (11)
C50.0369 (18)0.0294 (15)0.0293 (15)−0.0086 (13)−0.0078 (13)0.0016 (11)
C60.0302 (15)0.0275 (14)0.0246 (13)−0.0069 (12)−0.0072 (11)0.0009 (11)
C70.0236 (15)0.0506 (18)0.0302 (15)0.0012 (13)−0.0049 (12)0.0033 (13)
C80.0284 (16)0.0504 (18)0.0238 (14)−0.0026 (13)0.0000 (12)0.0025 (12)
C90.0246 (15)0.0250 (14)0.0285 (14)−0.0058 (11)−0.0057 (11)0.0005 (11)
C100.0222 (15)0.0561 (19)0.0311 (15)−0.0005 (13)−0.0045 (12)−0.0085 (13)
C110.0314 (17)0.0554 (19)0.0238 (14)−0.0041 (14)0.0008 (12)−0.0086 (12)
N10.0317 (14)0.0398 (14)0.0238 (12)−0.0028 (11)−0.0058 (10)0.0009 (10)
N20.0296 (14)0.0589 (16)0.0300 (13)−0.0044 (12)−0.0035 (11)0.0003 (11)
N30.0286 (13)0.0324 (13)0.0247 (11)−0.0038 (10)−0.0027 (10)−0.0013 (9)
O10.0406 (12)0.0466 (12)0.0289 (10)−0.0073 (10)0.0000 (9)−0.0030 (9)
O20.0524 (13)0.0422 (12)0.0344 (11)0.0043 (10)−0.0178 (9)−0.0028 (9)
O30.0408 (12)0.0480 (12)0.0257 (10)−0.0010 (10)−0.0059 (9)−0.0036 (9)
O40.0322 (12)0.0707 (15)0.0306 (11)0.0062 (11)−0.0125 (9)−0.0015 (10)
Zn10.0329 (3)0.0407 (3)0.0206 (2)−0.0017 (2)−0.00443 (19)−0.00010 (19)
Geometric parameters (Å, º) top
C1—N21.301 (3)C7—H70.9300
C1—N11.350 (3)C8—C91.384 (4)
C1—H1A0.9300C8—H80.9300
C2—N11.317 (3)C9—C101.389 (3)
C2—N31.323 (3)C9—C9ii1.481 (5)
C2—H2A0.9300C10—C111.374 (4)
C3—N31.453 (3)C10—H100.9300
C3—C41.500 (4)C11—H110.9300
C3—H3A0.9700N1—Zn12.096 (2)
C3—H3B0.9700N2—N31.354 (3)
C4—C4i1.524 (5)O1—Zn12.1693 (19)
C4—H4A0.9700O1—H1C0.8500
C4—H4B0.9700O1—H1D0.8499
C5—O41.238 (3)O2—Zn12.1234 (18)
C5—O31.272 (3)O2—H2C0.8500
C5—C61.507 (4)O2—H2D0.8500
C6—C111.378 (4)Zn1—N1iii2.096 (2)
C6—C71.381 (3)Zn1—O2iii2.1234 (18)
C7—C81.378 (4)Zn1—O1iii2.1693 (19)
N2—C1—N1114.6 (3)C11—C10—H10119.2
N2—C1—H1A122.7C9—C10—H10119.2
N1—C1—H1A122.7C10—C11—C6122.0 (2)
N1—C2—N3109.7 (2)C10—C11—H11119.0
N1—C2—H2A125.1C6—C11—H11119.0
N3—C2—H2A125.1C2—N1—C1103.1 (2)
N3—C3—C4114.8 (2)C2—N1—Zn1128.25 (18)
N3—C3—H3A108.6C1—N1—Zn1127.55 (18)
C4—C3—H3A108.6C1—N2—N3102.5 (2)
N3—C3—H3B108.6C2—N3—N2110.0 (2)
C4—C3—H3B108.6C2—N3—C3131.7 (2)
H3A—C3—H3B107.5N2—N3—C3118.2 (2)
C3—C4—C4i109.7 (3)Zn1—O1—H1C108.1
C3—C4—H4A109.7Zn1—O1—H1D107.9
C4i—C4—H4A109.7H1C—O1—H1D107.4
C3—C4—H4B109.7Zn1—O2—H2C111.6
C4i—C4—H4B109.7Zn1—O2—H2D111.7
H4A—C4—H4B108.2H2C—O2—H2D109.6
O4—C5—O3124.7 (2)N1iii—Zn1—N1180.00 (5)
O4—C5—C6118.0 (2)N1iii—Zn1—O293.74 (8)
O3—C5—C6117.3 (2)N1—Zn1—O286.26 (8)
C11—C6—C7116.7 (2)N1iii—Zn1—O2iii86.26 (8)
C11—C6—C5122.7 (2)N1—Zn1—O2iii93.74 (8)
C7—C6—C5120.6 (2)O2—Zn1—O2iii180.00 (9)
C8—C7—C6121.5 (2)N1iii—Zn1—O193.19 (8)
C8—C7—H7119.3N1—Zn1—O186.81 (8)
C6—C7—H7119.3O2—Zn1—O187.85 (8)
C7—C8—C9122.0 (2)O2iii—Zn1—O192.15 (8)
C7—C8—H8119.0N1iii—Zn1—O1iii86.81 (8)
C9—C8—H8119.0N1—Zn1—O1iii93.19 (8)
C8—C9—C10116.1 (2)O2—Zn1—O1iii92.15 (8)
C8—C9—C9ii121.5 (3)O2iii—Zn1—O1iii87.85 (8)
C10—C9—C9ii122.4 (3)O1—Zn1—O1iii180.00 (10)
C11—C10—C9121.7 (2)
N3—C3—C4—C4i−177.5 (3)N2—C1—N1—C20.1 (3)
O4—C5—C6—C11−171.9 (3)N2—C1—N1—Zn1−168.61 (19)
O3—C5—C6—C117.6 (4)N1—C1—N2—N30.0 (3)
O4—C5—C6—C77.9 (4)N1—C2—N3—N20.2 (3)
O3—C5—C6—C7−172.7 (2)N1—C2—N3—C3−176.2 (2)
C11—C6—C7—C8−1.7 (4)C1—N2—N3—C2−0.1 (3)
C5—C6—C7—C8178.6 (2)C1—N2—N3—C3176.9 (2)
C6—C7—C8—C90.3 (4)C4—C3—N3—C2−9.0 (4)
C7—C8—C9—C101.5 (4)C4—C3—N3—N2174.8 (2)
C7—C8—C9—C9ii−179.6 (3)C2—N1—Zn1—O2−141.6 (2)
C8—C9—C10—C11−1.8 (4)C1—N1—Zn1—O224.4 (2)
C9ii—C9—C10—C11179.3 (3)C2—N1—Zn1—O2iii38.4 (2)
C9—C10—C11—C60.4 (5)C1—N1—Zn1—O2iii−155.6 (2)
C7—C6—C11—C101.3 (4)C2—N1—Zn1—O1−53.5 (2)
C5—C6—C11—C10−178.9 (3)C1—N1—Zn1—O1112.5 (2)
N3—C2—N1—C1−0.2 (3)C2—N1—Zn1—O1iii126.5 (2)
N3—C2—N1—Zn1168.47 (17)C1—N1—Zn1—O1iii−67.5 (2)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C6–C11 benzene ring.
D—H···AD—HH···AD···AD—H···A
C2—H2A···O4iv0.932.503.342 (3)150
O1—H1D···O3v0.852.072.825 (3)148
O1—H1C···O30.851.952.783 (2)167
O2—H2C···O4vi0.851.852.642 (3)155
O2—H2D···O30.852.062.839 (3)151
C3—H3B···Cg0.972.823.552 (3)133
Symmetry codes: (iv) x+1, y−1, z; (v) −x+1, −y+1, −z; (vi) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Zn(C8H12N6)(H2O)4](C14H8O4)
Mr569.89
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.4344 (15), 7.1490 (18), 13.539 (3)
α, β, γ (°)89.250 (4), 81.348 (4), 72.620 (3)
V (Å3)587.3 (2)
Z1
Radiation typeMo Kα
µ (mm−1)1.11
Crystal size (mm)0.21 × 0.19 × 0.17
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.792, 0.828
No. of measured, independent and
observed [I > 2σ(I)] reflections		3162, 2299, 1788
Rint0.032
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.080, 0.92
No. of reflections2237
No. of parameters169
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.47, −0.31

Computer programs: SMART (Bruker 2000), SAINT (Bruker 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C6–C11 benzene ring.
D—H···AD—HH···AD···AD—H···A
C2—H2A···O4i0.932.503.342 (3)150.2
O1—H1D···O3ii0.852.072.825 (3)148.3
O1—H1C···O30.851.952.783 (2)166.6
O2—H2C···O4iii0.851.852.642 (3)154.7
O2—H2D···O30.852.062.839 (3)151.4
C3—H3B···Cg0.972.823.552 (3)133.2
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z.
 

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFerey, G., Mellot-Draznieks, C., Serre, C. & Millange, F. (2005). Acc. Chem. Res. 38, 217–225.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationGu, Z.-G., Xu, Y.-F., Zhou, X.-H., Zuo, J.-L. & You, X.-Z. (2008). Cryst. Growth Des. 8, 1306–1312.  Web of Science CSD CrossRef CAS Google Scholar
 First citationKitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334–2375.  Web of Science CrossRef CAS Google Scholar
 First citationLiu, X., Liu, K., Yang, Y. & Li, B. (2008). Inorg. Chem. Commun. 11, 1273–1275.  Web of Science CSD CrossRef Google Scholar
 First citationRoy, S., Mahata, G. & Biradha, K. (2009). Cryst. Growth Des. 9, 5006–5008.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, L.-Y., Yang, Y., Liu, K., Li, B.-L. & Zhang, Y. (2008). Cryst. Growth Des. 8, 3902–3904.  Web of Science CSD CrossRef CAS Google Scholar
 First citationZhang, Y. B., Zhang, W. X., Feng, F. Y., Zhang, J. P. & Chen, X. M. (2009). Angew. Chem. Int. Ed. 48, 5287–5290.  Web of Science CSD CrossRef CAS Google Scholar
 First citationZhu, X., Liu, X.-G., Li, B.-L. & Zhang, Y. (2009). CrystEngComm, 11, 997–1000.  Web of Science CSD CrossRef CAS Google Scholar

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page m1404
https://doi.org/10.1107/S160053681003970X
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