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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 68| Part 10| October 2012| Pages m1268-m1269
https://doi.org/10.1107/S1600536812038883

Poly[di­ammonium [(μ4-butane-1,2,3,4-tetra­carboxyl­ato)zincate] tetra­hydrate]

Shouwen Jin,a* Yanfei Huang,a Shuaishuai Wei,a Yong Zhoua and Yingping Zhoua

aTianmu College of ZheJiang A & F University, Lin'An 311300, People's Republic of China
*Correspondence e-mail: shouwenjin@yahoo.cn

(Received 31 August 2012; accepted 11 September 2012; online 15 September 2012)

In the title compound, {(NH4)2[Zn(C8H6O8)]·4H2O}n, the asymmetric unit contains one ammonium cation, half of a butane-1,2,3,4-tetra­carboxyl­ate anion, one Zn2+ cation and two water mol­ecules. The butane-1,2,3,4-tetra­carboxyl­ate ligand is located about an inversion centre at the mid-point of the central C—C bond. The Zn2+ cation is situated on a twofold rotation axis and is surrounded by four O atoms from four symmetry-related butane-1,2,3,4-tetra­carboxyl­ate anions in a distorted tetra­hedral environment. In turn, each anion coordinates to four Zn2+ cations. The bridging mode of the anions leads to a three-dimensional framework structure with channels extending along [110] and [010] in which the ammonium cations and the water mol­ecules are located. N—H⋯O and O—H⋯O hydrogen bonding between the cations and water mol­ecules and the uncoordinating O atoms of the carboxyl­ate groups consolidates the crystal packing.

Related literature

For general background to coordination compounds derived from carb­oxy­lic acids, see: Jin & Chen (2007a[Jin, S. W. & Chen, W. Z. (2007a). Polyhedron, 26, 3074-3084.],b[Jin, S. W. & Chen, W. Z. (2007b). Inorg. Chim. Acta, 12, 3756-3764.]); Jin et al. (2007[Jin, S. W., Wang, D. Q. & Chen, W. Z. (2007). Inorg. Chem. Commun. 10, 685-689.]); Rueff et al. (2001[Rueff, J. M., Masciocchi, N., Rabu, P., Sironi, A. & Skoulios, A. (2001). Eur. J. Inorg. Chem. pp. 2843-2848.]); Strachan et al. (2007[Strachan, C. J., Rades, T. & Gordon, K. C. (2007). J. Pharm. Pharmacol. 59, 261-269.]). For hydrogen bonding, see: Desiraju (2002[Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.]).

[Scheme 1]

Experimental

Crystal data

  • (NH4)2[Zn(C8H6O8)]·4H2O

  • Mr = 403.65

  • Monoclinic, C 2/c

  • a = 14.1153 (12) Å

  • b = 8.8505 (8) Å

  • c = 13.5704 (11) Å

  • β = 111.761 (2)°

  • V = 1574.5 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.63 mm−1

  • T = 298 K

  • 0.36 × 0.19 × 0.12 mm
Data collection

  • Bruker SMART 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.697, Tmax = 0.823

  • 3841 measured reflections

  • 1386 independent reflections

  • 1167 reflections with I > 2σ(I)

  • Rint = 0.089
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.156

  • S = 1.02

  • 1386 reflections

  • 105 parameters

  • H-atom parameters constrained

  • Δρmax = 1.53 e Å−3

  • Δρmin = −1.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O6—H6D⋯O4i 0.85 1.97 2.814 (4) 173
O6—H6C⋯O3ii 0.85 1.99 2.833 (5) 173
O5—H5D⋯O6iii 0.85 1.97 2.805 (5) 168
O5—H5C⋯O1 0.85 1.98 2.816 (4) 167
N1—H1B⋯O2i 0.90 2.31 2.981 (5) 131
N1—H1B⋯O3i 0.90 2.30 3.009 (5) 136
N1—H1A⋯O5iv 0.90 2.54 3.153 (5) 126
N1—H1A⋯O6v 0.90 2.24 2.948 (5) 135
N1—H1D⋯O2vi 0.90 1.91 2.810 (5) 178
N1—H1C⋯O5 0.90 1.86 2.761 (5) 177
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x, y+1, z; (iv) -x+1, -y+2, -z+1; (v) [x, -y+1, z-{\script{1\over 2}}]; (vi) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SMART 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812038883/wm2679sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038883/wm2679Isup2.hkl

checkCIF report


Comment top

Various derivatives of carboxylic acids have been widely used in pharmaceutical chemistry (Strachan et al., 2007), supramolecular chemistry (Desiraju, 2002), and coordination chemistry (Rueff et al., 2001). As an extension of our studies concentrating on coordination compounds with carboxylate ligands (Jin & Chen, 2007a,b; Jin et al., 2007), we report here the crystal structure of (NH4)2[Zn(C8H6O8)].4H2O, (I).

The asymmetric unit of compound (I) contains half of the butane-1,2,3,4-tetracarboxylate anion, one ammonium cation, two water molecules and one Zn2+ cation. The butane-1,2,3,4-tetracarboxylate anion has an inversion centre located at the mid point of the central 3-C, and 4-C bond (symmetry code -x, -y, -z). The Zn2+ ion lies on a twofold rotation axis. It is surrounded by four O atoms from four symmetry-related butane-1,2,3,4-tetracarboxylate anions, forming a tetrahedral coordination geometry. Of the four coordinating O atoms, two come from the carboxylate groups in 1-position, while the other two come from the carboxylate groups in 3-position. The Zn—O bond lengths are almost equal.

The Zn2+ cations and the coordinating butane-1,2,3,4-tetracarboxylate anions form a three-dimensional network with channels extending along [110] and [010] (Fig. 2). In the channels water molecules and ammonium cations are present. They are hydrogen bonded to each other through O—H···O and N—H···O interactions and also hydrogen-bonded to the uncoordinating O atoms of the carboxylate groups of the anion.

Single crystals of the title compound were obtained by reacting zinc(II) acetate dihydrate with butane-1,2,3,4-tetracarboxylic acid in basic solution in the presence of 3,5-dimethyl pyrazole. However, 3,5-dimethyl pyrazole does not appear in the title compound. It should be noted that single crystals could not be obtained by evaporating an appropriate solution of the title compound in water or organic solvents. We found that it can be dissolved in a concentrated solution of ammonia; thus its single crystals were grown by slow evaporating its ammonia solution.

Related literature top

For general background to coordination compounds derived from carboxylic acids, see: Jin & Chen (2007a,b); Jin et al. (2007); Rueff et al. (2001); Strachan et al. (2007); Desiraju (2002).

Experimental top

Butane-1,2,3,4-tetracarboxylic acid (22.3.1 mg, 0.10 mmol) was dissolved in 10 ml of methanol, to this solution zinc acetate dihydrate (42.6 mg, 0.2 mmol), and 3,5-dimethylpyrazole (19.2 mg, 0.2 mmol) was added. The solution was stirred for about 2 h at room temperature, and a large amount of precipitate formed. To the suspensition concentrated ammonia solution was added until the precipitate dissolved completely. The solution was filtered into a test tube and was left standing at room temperature. Several days later colorless block crystals could be obtained.

Refinement top

H atoms bonded to O, and N atoms were located in a difference Fourier map. Their bond lengths were constrained to values of O—H of 0.85 Å and N—H of 0.90 Å and they were allowed to ride on their parent atoms. All other H atoms were positioned geometrically with C—H = 0.97–0.98 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Structure description top

Various derivatives of carboxylic acids have been widely used in pharmaceutical chemistry (Strachan et al., 2007), supramolecular chemistry (Desiraju, 2002), and coordination chemistry (Rueff et al., 2001). As an extension of our studies concentrating on coordination compounds with carboxylate ligands (Jin & Chen, 2007a,b; Jin et al., 2007), we report here the crystal structure of (NH4)2[Zn(C8H6O8)].4H2O, (I).

The asymmetric unit of compound (I) contains half of the butane-1,2,3,4-tetracarboxylate anion, one ammonium cation, two water molecules and one Zn2+ cation. The butane-1,2,3,4-tetracarboxylate anion has an inversion centre located at the mid point of the central 3-C, and 4-C bond (symmetry code -x, -y, -z). The Zn2+ ion lies on a twofold rotation axis. It is surrounded by four O atoms from four symmetry-related butane-1,2,3,4-tetracarboxylate anions, forming a tetrahedral coordination geometry. Of the four coordinating O atoms, two come from the carboxylate groups in 1-position, while the other two come from the carboxylate groups in 3-position. The Zn—O bond lengths are almost equal.

The Zn2+ cations and the coordinating butane-1,2,3,4-tetracarboxylate anions form a three-dimensional network with channels extending along [110] and [010] (Fig. 2). In the channels water molecules and ammonium cations are present. They are hydrogen bonded to each other through O—H···O and N—H···O interactions and also hydrogen-bonded to the uncoordinating O atoms of the carboxylate groups of the anion.

Single crystals of the title compound were obtained by reacting zinc(II) acetate dihydrate with butane-1,2,3,4-tetracarboxylic acid in basic solution in the presence of 3,5-dimethyl pyrazole. However, 3,5-dimethyl pyrazole does not appear in the title compound. It should be noted that single crystals could not be obtained by evaporating an appropriate solution of the title compound in water or organic solvents. We found that it can be dissolved in a concentrated solution of ammonia; thus its single crystals were grown by slow evaporating its ammonia solution.

For general background to coordination compounds derived from carboxylic acids, see: Jin & Chen (2007a,b); Jin et al. (2007); Rueff et al. (2001); Strachan et al. (2007); Desiraju (2002).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular components of the structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. The packing of the structure of (I) showing the channel formation. Hydrogen bonds are displayed with dashed lines.
Poly[diammonium [(µ4-butane-1,2,3,4-tetracarboxylato)zincate] tetrahydrate] top
Crystal data top
(NH4)2[Zn(C8H6O8)]·4H2OF(000) = 840
Mr = 403.65Dx = 1.703 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2092 reflections
a = 14.1153 (12) Åθ = 2.8–27.6°
b = 8.8505 (8) ŵ = 1.63 mm−1
c = 13.5704 (11) ÅT = 298 K
β = 111.761 (2)°Block, colorless
V = 1574.5 (2) Å30.36 × 0.19 × 0.12 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		1386 independent reflections
Radiation source: fine-focus sealed tube1167 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.089
phi and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −16→16
Tmin = 0.697, Tmax = 0.823k = −9→10
3841 measured reflectionsl = −16→12
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1135P)2]
where P = (Fo2 + 2Fc2)/3
1386 reflections(Δ/σ)max < 0.001
105 parametersΔρmax = 1.53 e Å−3
0 restraintsΔρmin = −1.30 e Å−3
Crystal data top
(NH4)2[Zn(C8H6O8)]·4H2OV = 1574.5 (2) Å3
Mr = 403.65Z = 4
Monoclinic, C2/cMo Kα radiation
a = 14.1153 (12) ŵ = 1.63 mm−1
b = 8.8505 (8) ÅT = 298 K
c = 13.5704 (11) Å0.36 × 0.19 × 0.12 mm
β = 111.761 (2)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		1386 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		1167 reflections with I > 2σ(I)
Tmin = 0.697, Tmax = 0.823Rint = 0.089
3841 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.02Δρmax = 1.53 e Å−3
1386 reflectionsΔρmin = −1.30 e Å−3
105 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
Zn10.50000.50029 (6)0.75000.0196 (3)
N10.6212 (3)0.8163 (4)0.5030 (3)0.0379 (9)
H1C0.58610.84800.54270.045*
H1D0.68360.85880.52870.045*
H1A0.58840.84400.43500.045*
H1B0.62690.71500.50620.045*
O10.41853 (19)0.6486 (3)0.6404 (2)0.0291 (7)
O20.3143 (2)0.4535 (4)0.5878 (2)0.0340 (7)
O30.3480 (3)0.4657 (4)0.3648 (3)0.0413 (8)
O40.44049 (18)0.6425 (3)0.32532 (19)0.0262 (6)
O50.5186 (2)0.9191 (4)0.6280 (3)0.0516 (9)
H5C0.49230.83950.64200.062*
H5D0.55260.96350.68590.062*
O60.6370 (2)0.0991 (3)0.7995 (2)0.0470 (8)
H6C0.70080.08710.81630.056*
H6D0.61890.17870.76220.056*
C10.3369 (3)0.5846 (4)0.5744 (3)0.0210 (8)
C20.3742 (3)0.5970 (5)0.3645 (3)0.0244 (9)
C30.2700 (3)0.6794 (4)0.4801 (3)0.0203 (8)
H30.21110.61800.43780.024*
C40.3286 (3)0.7247 (4)0.4090 (3)0.0254 (9)
H4A0.28270.78230.34960.030*
H4B0.38360.79180.44940.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0194 (4)0.0239 (5)0.0197 (5)0.0000.0122 (3)0.000
N10.039 (2)0.039 (2)0.042 (2)−0.0020 (16)0.0213 (18)−0.0064 (16)
O10.0260 (14)0.0341 (16)0.0247 (15)0.0003 (12)0.0064 (12)0.0014 (12)
O20.0367 (17)0.0293 (16)0.0373 (18)0.0002 (14)0.0152 (14)0.0075 (14)
O30.053 (2)0.0317 (17)0.056 (2)−0.0036 (16)0.0396 (18)−0.0033 (15)
O40.0259 (13)0.0337 (15)0.0268 (14)0.0008 (12)0.0187 (12)−0.0014 (11)
O50.061 (2)0.055 (2)0.053 (2)−0.0072 (18)0.0373 (18)−0.0061 (17)
O60.0522 (18)0.0453 (19)0.0493 (19)0.0042 (16)0.0257 (16)0.0129 (16)
C10.0232 (18)0.028 (2)0.0190 (18)0.0074 (16)0.0157 (16)−0.0022 (15)
C20.0236 (18)0.035 (2)0.0190 (19)0.0058 (17)0.0126 (16)−0.0008 (16)
C30.0197 (17)0.026 (2)0.0183 (18)0.0006 (15)0.0108 (15)−0.0012 (14)
C40.0267 (19)0.031 (2)0.025 (2)0.0040 (17)0.0170 (17)0.0035 (16)
Geometric parameters (Å, º) top
Zn1—O4i1.996 (2)O4—Zn1i1.996 (2)
Zn1—O4ii1.996 (2)O5—H5C0.8499
Zn1—O1iii1.998 (3)O5—H5D0.8500
Zn1—O11.998 (3)O6—H6C0.8500
N1—H1C0.9000O6—H6D0.8500
N1—H1D0.9001C1—C31.529 (5)
N1—H1A0.9001C2—C41.531 (5)
N1—H1B0.9000C3—C41.540 (5)
O1—C11.298 (4)C3—C3iv1.548 (7)
O2—C11.234 (5)C3—H30.9800
O3—C21.220 (5)C4—H4A0.9700
O4—C21.300 (4)C4—H4B0.9700
O4i—Zn1—O4ii101.42 (14)O2—C1—C3121.7 (3)
O4i—Zn1—O1iii124.21 (10)O1—C1—C3116.9 (3)
O4ii—Zn1—O1iii105.67 (10)O3—C2—O4124.1 (3)
O4i—Zn1—O1105.67 (10)O3—C2—C4122.0 (4)
O4ii—Zn1—O1124.21 (10)O4—C2—C4113.9 (3)
O1iii—Zn1—O197.83 (15)C1—C3—C4111.0 (3)
H1C—N1—H1D108.3C1—C3—C3iv110.1 (3)
H1C—N1—H1A109.9C4—C3—C3iv110.9 (4)
H1D—N1—H1A109.9C1—C3—H3108.2
H1C—N1—H1B109.9C4—C3—H3108.2
H1D—N1—H1B109.9C3iv—C3—H3108.2
H1A—N1—H1B108.9C2—C4—C3117.2 (3)
C1—O1—Zn1110.2 (2)C2—C4—H4A108.0
C2—O4—Zn1i121.1 (2)C3—C4—H4A108.0
H5C—O5—H5D108.7C2—C4—H4B108.0
H6C—O6—H6D108.6C3—C4—H4B108.0
O2—C1—O1121.4 (3)H4A—C4—H4B107.2
O4i—Zn1—O1—C171.4 (2)O1—C1—C3—C462.1 (4)
O4ii—Zn1—O1—C1−44.7 (3)O2—C1—C3—C3iv118.4 (4)
O1iii—Zn1—O1—C1−159.7 (3)O1—C1—C3—C3iv−61.2 (4)
Zn1—O1—C1—O25.1 (4)O3—C2—C4—C315.6 (5)
Zn1—O1—C1—C3−175.4 (2)O4—C2—C4—C3−165.7 (3)
Zn1i—O4—C2—O34.7 (5)C1—C3—C4—C256.4 (4)
Zn1i—O4—C2—C4−173.9 (2)C3iv—C3—C4—C2179.2 (3)
O2—C1—C3—C4−118.4 (4)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1, z+1/2; (iii) −x+1, y, −z+3/2; (iv) −x+1/2, −y+3/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6D···O4i0.851.972.814 (4)173
O6—H6C···O3v0.851.992.833 (5)173
O5—H5D···O6vi0.851.972.805 (5)168
O5—H5C···O10.851.982.816 (4)167
N1—H1B···O2i0.902.312.981 (5)131
N1—H1B···O3i0.902.303.009 (5)136
N1—H1A···O5vii0.902.543.153 (5)126
N1—H1A···O6viii0.902.242.948 (5)135
N1—H1D···O2ix0.901.912.810 (5)178
N1—H1C···O50.901.862.761 (5)177
Symmetry codes: (i) −x+1, −y+1, −z+1; (v) x+1/2, −y+1/2, z+1/2; (vi) x, y+1, z; (vii) −x+1, −y+2, −z+1; (viii) x, −y+1, z−1/2; (ix) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula(NH4)2[Zn(C8H6O8)]·4H2O
Mr403.65
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)14.1153 (12), 8.8505 (8), 13.5704 (11)
β (°) 111.761 (2)
V (Å3)1574.5 (2)
Z4
Radiation typeMo Kα
µ (mm−1)1.63
Crystal size (mm)0.36 × 0.19 × 0.12
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.697, 0.823
No. of measured, independent and
observed [I > 2σ(I)] reflections		3841, 1386, 1167
Rint0.089
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.156, 1.02
No. of reflections1386
No. of parameters105
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.53, −1.30

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6D···O4i0.851.972.814 (4)172.8
O6—H6C···O3ii0.851.992.833 (5)173.1
O5—H5D···O6iii0.851.972.805 (5)167.5
O5—H5C···O10.851.982.816 (4)167.4
N1—H1B···O2i0.902.312.981 (5)131.4
N1—H1B···O3i0.902.303.009 (5)135.7
N1—H1A···O5iv0.902.543.153 (5)125.8
N1—H1A···O6v0.902.242.948 (5)134.7
N1—H1D···O2vi0.901.912.810 (5)177.5
N1—H1C···O50.901.862.761 (5)177.4
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, y+1, z; (iv) −x+1, −y+2, −z+1; (v) x, −y+1, z−1/2; (vi) x+1/2, y+1/2, z.
 

Acknowledgements

We gratefully acknowledge financial support by the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the Innovation Project of Zhejiang A & F University.

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages m1268-m1269
https://doi.org/10.1107/S1600536812038883
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