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Acta Cryst. (2012). E68, m462-m463    [ doi:10.1107/S1600536812011439 ]

Bis(guanidinium) tris(pyridine-2,6-dicarboxylato-[kappa]3O2,N,O6)zirconate(II) tetrahydrate

M. Tabatabaee, M. Adineh, Z. Derikvand and J. Attar Gharamaleki

Abstract top

In the title complex, (CH6N3)2[Zr(C7H3NO4)3]·4H2O, the ZrIV ion lies on a twofold rotation axes and is coordinated by six O and three N atoms of three tridentate pyridine-2,6-dicarboxylate ligands, forming a slightly distorted tricapped trigonal-prismatic geometry. In the crystal, O-H...O and N-H...O hydrogen bonds link the components into a three-dimensional network.

Comment top

In recent years, our research group has been interested in the synthesis of proton transfer compounds and study of their behavior with metal ions. We have focused on the proton delivery of polycarboxylic acids. Pyridine-2,6-dicarboxylic acid (pydcH2) is a very important carboxylate derivative and has attracted much interest in coordination chemistry. This is the acid we have utilized widely in our studies (Tabatabaee et al., 2010, 2011a, 2011b, 2011c, 2012; Derikvand et al., 2010; Attar Gharamaleki et al., 2009). In this paper we report the crystal structure of the title complex (I). The ZrIV ion lies on a twofold rotation axis. The asymmetric unit and the symmetry complete cation is shown in Fig. 1. The ZrIV atom is coordinated by three tridentate pydc ligands forming a slightly distorted tricapped trigonal prismatic environment (Fig. 2). The Zr—N distances and Zr—O distances are consistent with those found in (pydaH)2[Zr(pydc)3].5H2O (Aghabozorg et al., 2005). In the crystal, O—H···O and N—H···O hydrogen bonds (Table 1) link the components into a three-dimensional network (Fig. 3).

Related literature top

For related structures, see: Aghabozorg et al. (2005); Tabatabaee et al. (2009, 2010, 2011a,b,c, 2012); Derikvand et al. (2010); Attar Gharamaleki et al. (2009).

Experimental top

An aqueous solution of ZrOCl2.8H2O, (161 mg, 0.5 mmol) in water (5 ml) was added to a stirring solution of (20 ml) pyridine-2,6-dicarboxylic acid (176 mg, 1 mmol) and guanidine hydrochloride (95 mg, 1 mmol). The reaction mixture was stirred at 298K for 1 h. Colorless crystals of the title compound were obtained after 4 days by slow evaporation of the solvent at room temperature.

Refinement top

H atoms bonded to C atoms were placed in calculated positions. The H atoms of water molecules and NH2 groups were located in difference Fourier maps and included in 'as found' positions. All hydrogen atoms were refined in isotropic approximatiom in a riding-model approximation with Uiso(H) parameters equal to 1.2 Ueq(C), 1.5 Ueq(O,N).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 1999) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with ellipsoids drawn at the 50% probability level. The unlabeled atoms are related by the symmetry operator (-x+1, y, -z+1/2). Only the symmetry unique anions and water molecules are shown.
[Figure 2] Fig. 2. View of the coordination environment of the ZrIV ion.
[Figure 3] Fig. 3. Part of the crystal structure of (I). The donor to acceptor distances of the hydrogen bonds are shown as dotted lines.
Bis(guanidinium) tris(pyridine-2,6-dicarboxylato- κ3O2,N,O6)zirconate(II) tetrahydrate top
Crystal data top
(CH6N3)2[Zr(C7H3NO4)3]·4H2OF(000) = 1592
Mr = 778.77Dx = 1.672 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 4151 reflections
a = 17.2444 (9) Åθ = 2.3–26.0°
b = 10.8583 (5) ŵ = 0.45 mm−1
c = 16.5268 (8) ÅT = 120 K
V = 3094.6 (3) Å3Prism, colorless
Z = 40.17 × 0.15 × 0.07 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer		4116 independent reflections
Radiation source: normal-focus sealed tube2884 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
ω scansθmax = 29.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −23→23
Tmin = 0.884, Tmax = 0.970k = −14→14
32229 measured reflectionsl = −22→22
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)] = 0.056Hydrogen site location: mixed
wR(F2) = 0.146H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0562P)2 + 8.430P]
where P = (Fo2 + 2Fc2)/3
4116 reflections(Δ/σ)max < 0.001
223 parametersΔρmax = 0.87 e Å−3
0 restraintsΔρmin = −0.47 e Å−3
Crystal data top
(CH6N3)2[Zr(C7H3NO4)3]·4H2OV = 3094.6 (3) Å3
Mr = 778.77Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 17.2444 (9) ŵ = 0.45 mm−1
b = 10.8583 (5) ÅT = 120 K
c = 16.5268 (8) Å0.17 × 0.15 × 0.07 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer		4116 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		2884 reflections with I > 2σ(I)
Tmin = 0.884, Tmax = 0.970Rint = 0.068
32229 measured reflectionsθmax = 29.0°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.146Δρmax = 0.87 e Å−3
S = 1.07Δρmin = −0.47 e Å−3
4116 reflectionsAbsolute structure: ?
223 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Zr10.50000.72625 (4)0.25000.01631 (13)
O10.38154 (13)0.6592 (2)0.28200 (14)0.0245 (5)
O20.25204 (15)0.6675 (3)0.27362 (17)0.0349 (6)
O30.54360 (12)0.8668 (2)0.16530 (13)0.0226 (5)
O40.53142 (16)1.0370 (2)0.09047 (17)0.0362 (6)
O50.47334 (14)0.6443 (2)0.12914 (14)0.0236 (5)
O60.42065 (17)0.4926 (2)0.05627 (15)0.0354 (6)
N10.40034 (15)0.8418 (2)0.18731 (16)0.0214 (5)
N20.50000.5072 (3)0.25000.0171 (7)
C10.32630 (19)0.8123 (3)0.20019 (19)0.0225 (6)
C20.2655 (2)0.8764 (3)0.1641 (2)0.0292 (7)
H2A0.21310.85330.17310.035*
C30.2842 (2)0.9750 (3)0.1146 (2)0.0295 (7)
H3A0.24411.02160.08980.035*
C40.3609 (2)1.0061 (3)0.1010 (2)0.0273 (7)
H4A0.37431.07330.06700.033*
C50.41742 (19)0.9359 (3)0.13861 (19)0.0219 (6)
C60.31649 (18)0.7054 (3)0.25566 (19)0.0218 (6)
C70.50369 (18)0.9516 (3)0.12932 (18)0.0205 (6)
C80.47612 (18)0.4462 (3)0.18438 (19)0.0222 (6)
C90.4742 (2)0.3187 (3)0.1823 (2)0.0273 (7)
H9A0.45570.27610.13600.033*
C100.50000.2551 (4)0.25000.0284 (10)
H10A0.50000.16760.25000.034*
C110.45375 (19)0.5307 (3)0.1163 (2)0.0240 (6)
N30.33875 (17)0.4432 (3)0.38628 (19)0.0312 (7)
H3NA0.34820.50160.36160.047*
H3NB0.37520.40390.41120.047*
N40.25724 (18)0.3150 (3)0.45574 (18)0.0314 (7)
H4NA0.29710.27490.46520.047*
H4NB0.21580.28850.46260.047*
N50.20814 (17)0.4727 (3)0.3776 (2)0.0364 (8)
H5NA0.21660.53440.34390.055*
H5NB0.16540.45170.38650.055*
C120.26720 (19)0.4098 (3)0.4060 (2)0.0268 (7)
O1W0.39648 (14)0.2667 (2)−0.01609 (15)0.0279 (5)
H1WA0.41950.2642−0.06070.042*
H1WB0.40260.33770.01000.042*
O2W0.58669 (15)0.2479 (2)0.01935 (16)0.0310 (6)
H2WA0.57680.2747−0.02870.047*
H2WB0.56310.17220.03190.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zr10.0173 (2)0.0148 (2)0.0169 (2)0.000−0.00061 (15)0.000
O10.0241 (12)0.0232 (11)0.0261 (11)−0.0009 (9)−0.0003 (9)0.0031 (9)
O20.0217 (12)0.0369 (15)0.0462 (15)−0.0031 (11)0.0017 (11)0.0095 (12)
O30.0213 (11)0.0233 (11)0.0232 (11)−0.0011 (9)0.0001 (9)0.0015 (9)
O40.0327 (13)0.0314 (14)0.0444 (15)−0.0070 (11)−0.0008 (12)0.0144 (12)
O50.0280 (11)0.0211 (11)0.0216 (11)−0.0035 (9)−0.0030 (9)0.0003 (9)
O60.0521 (16)0.0249 (12)0.0292 (13)−0.0054 (11)−0.0141 (12)−0.0004 (10)
N10.0231 (13)0.0206 (13)0.0205 (13)−0.0005 (10)0.0002 (10)−0.0013 (10)
N20.0149 (15)0.0161 (16)0.0203 (16)0.0000.0013 (13)0.000
C10.0236 (15)0.0212 (14)0.0228 (15)0.0026 (12)−0.0013 (12)0.0011 (12)
C20.0220 (16)0.0310 (18)0.0345 (19)0.0021 (13)−0.0010 (14)0.0036 (15)
C30.0256 (17)0.0336 (18)0.0294 (17)0.0077 (14)−0.0024 (14)0.0045 (15)
C40.0311 (17)0.0233 (16)0.0276 (16)0.0032 (13)−0.0045 (13)0.0055 (13)
C50.0260 (15)0.0163 (14)0.0235 (15)0.0008 (12)−0.0029 (12)−0.0002 (12)
C60.0192 (14)0.0226 (15)0.0235 (15)−0.0006 (11)0.0006 (12)−0.0015 (12)
C70.0258 (15)0.0177 (13)0.0179 (13)−0.0029 (12)−0.0011 (12)−0.0001 (11)
C80.0199 (14)0.0238 (16)0.0230 (15)−0.0014 (12)0.0018 (11)−0.0023 (13)
C90.0365 (18)0.0214 (16)0.0239 (16)−0.0030 (14)−0.0006 (13)−0.0025 (13)
C100.040 (3)0.020 (2)0.025 (2)0.000−0.003 (2)0.000
C110.0244 (15)0.0240 (16)0.0235 (15)−0.0002 (12)−0.0027 (12)−0.0022 (12)
N30.0240 (14)0.0321 (16)0.0375 (17)−0.0040 (12)0.0005 (12)0.0113 (13)
N40.0269 (15)0.0324 (16)0.0348 (16)−0.0033 (12)0.0041 (12)0.0093 (13)
N50.0208 (14)0.0441 (19)0.0444 (19)−0.0014 (13)0.0018 (13)0.0160 (15)
C120.0275 (17)0.0300 (17)0.0228 (16)−0.0002 (14)−0.0002 (12)0.0000 (13)
O1W0.0299 (12)0.0258 (12)0.0280 (12)−0.0058 (10)0.0040 (10)−0.0057 (10)
O2W0.0336 (13)0.0273 (12)0.0323 (13)−0.0075 (10)−0.0053 (11)0.0050 (10)
Geometric parameters (Å, º) top
Zr1—O32.203 (2)C3—H3A0.9500
Zr1—O3i2.203 (2)C4—C51.384 (4)
Zr1—O1i2.232 (2)C4—H4A0.9500
Zr1—O12.232 (2)C5—C71.505 (4)
Zr1—O52.234 (2)C8—C91.384 (5)
Zr1—O5i2.234 (2)C8—C111.503 (5)
Zr1—N1i2.366 (3)C9—C101.388 (4)
Zr1—N12.366 (3)C9—H9A0.9500
Zr1—N22.378 (4)C10—C9i1.388 (4)
O1—C61.304 (4)C10—H10A0.9500
O2—C61.222 (4)N3—C121.327 (4)
O3—C71.294 (4)N3—H3NA0.7713
O4—C71.225 (4)N3—H3NB0.8647
O5—C111.297 (4)N4—C121.329 (4)
O6—C111.217 (4)N4—H4NA0.8289
N1—C11.333 (4)N4—H4NB0.7790
N1—C51.334 (4)N5—C121.312 (4)
N2—C81.336 (4)N5—H5NA0.8832
N2—C8i1.336 (4)N5—H5NB0.7861
C1—C21.393 (5)O1W—H1WA0.8370
C1—C61.489 (5)O1W—H1WB0.8899
C2—C31.386 (5)O2W—H2WA0.8620
C2—H2A0.9500O2W—H2WB0.9408
C3—C41.382 (5)
O3—Zr1—O3i92.30 (12)N1—C1—C6113.2 (3)
O3—Zr1—O1i76.29 (8)C2—C1—C6124.6 (3)
O3i—Zr1—O1i133.53 (8)C3—C2—C1117.6 (3)
O3—Zr1—O1133.53 (8)C3—C2—H2A121.2
O3i—Zr1—O176.29 (8)C1—C2—H2A121.2
O1i—Zr1—O1141.94 (12)C4—C3—C2120.5 (3)
O3—Zr1—O577.18 (8)C4—C3—H3A119.8
O3i—Zr1—O5140.67 (8)C2—C3—H3A119.8
O1i—Zr1—O581.18 (9)C3—C4—C5117.8 (3)
O1—Zr1—O583.89 (9)C3—C4—H4A121.1
O3—Zr1—O5i140.67 (8)C5—C4—H4A121.1
O3i—Zr1—O5i77.18 (8)N1—C5—C4122.5 (3)
O1i—Zr1—O5i83.89 (9)N1—C5—C7111.5 (3)
O1—Zr1—O5i81.18 (9)C4—C5—C7126.0 (3)
O5—Zr1—O5i133.07 (12)O2—C6—O1124.9 (3)
O3—Zr1—N1i70.31 (8)O2—C6—C1121.0 (3)
O3i—Zr1—N1i66.58 (8)O1—C6—C1114.1 (3)
O1i—Zr1—N1i67.17 (9)O4—C7—O3124.9 (3)
O1—Zr1—N1i137.20 (9)O4—C7—C5121.7 (3)
O5—Zr1—N1i138.75 (9)O3—C7—C5113.4 (3)
O5i—Zr1—N1i70.75 (9)N2—C8—C9121.6 (3)
O3—Zr1—N166.58 (8)N2—C8—C11112.6 (3)
O3i—Zr1—N170.31 (8)C9—C8—C11125.9 (3)
O1i—Zr1—N1137.20 (9)C8—C9—C10118.1 (3)
O1—Zr1—N167.17 (9)C8—C9—H9A121.0
O5—Zr1—N170.75 (9)C10—C9—H9A121.0
O5i—Zr1—N1138.75 (9)C9—C10—C9i120.2 (4)
N1i—Zr1—N1115.98 (13)C9—C10—H10A119.9
O3—Zr1—N2133.85 (6)C9i—C10—H10A119.9
O3i—Zr1—N2133.85 (6)O6—C11—O5125.4 (3)
O1i—Zr1—N270.97 (6)O6—C11—C8121.6 (3)
O1—Zr1—N270.97 (6)O5—C11—C8113.1 (3)
O5—Zr1—N266.54 (6)C12—N3—H3NA123.4
O5i—Zr1—N266.54 (6)C12—N3—H3NB115.1
N1i—Zr1—N2122.01 (6)H3NA—N3—H3NB120.4
N1—Zr1—N2122.01 (6)C12—N4—H4NA114.6
C6—O1—Zr1125.7 (2)C12—N4—H4NB119.6
C7—O3—Zr1127.11 (19)H4NA—N4—H4NB122.8
C11—O5—Zr1125.4 (2)C12—N5—H5NA119.5
C1—N1—C5119.5 (3)C12—N5—H5NB120.7
C1—N1—Zr1119.9 (2)H5NA—N5—H5NB119.5
C5—N1—Zr1120.7 (2)N5—C12—N3119.5 (3)
C8—N2—C8i120.5 (4)N5—C12—N4121.6 (3)
C8—N2—Zr1119.8 (2)N3—C12—N4118.9 (3)
C8i—N2—Zr1119.8 (2)H1WA—O1W—H1WB113.4
N1—C1—C2122.2 (3)H2WA—O2W—H2WB114.3
O3—Zr1—O1—C6−5.4 (3)O3—Zr1—N2—C8i130.96 (17)
O3i—Zr1—O1—C674.6 (2)O3i—Zr1—N2—C8i−49.04 (17)
O1i—Zr1—O1—C6−138.4 (3)O1i—Zr1—N2—C8i83.72 (17)
O5—Zr1—O1—C6−71.2 (3)O1—Zr1—N2—C8i−96.28 (17)
O5i—Zr1—O1—C6153.4 (3)O5—Zr1—N2—C8i172.17 (17)
N1i—Zr1—O1—C6104.6 (3)O5i—Zr1—N2—C8i−7.83 (17)
N1—Zr1—O1—C60.5 (2)N1i—Zr1—N2—C8i38.12 (17)
N2—Zr1—O1—C6−138.4 (3)N1—Zr1—N2—C8i−141.88 (17)
O3i—Zr1—O3—C7−59.3 (2)C5—N1—C1—C20.3 (5)
O1i—Zr1—O3—C7166.3 (3)Zr1—N1—C1—C2−179.3 (2)
O1—Zr1—O3—C713.9 (3)C5—N1—C1—C6179.9 (3)
O5—Zr1—O3—C782.4 (2)Zr1—N1—C1—C60.4 (4)
O5i—Zr1—O3—C7−131.8 (2)N1—C1—C2—C3−1.2 (5)
N1i—Zr1—O3—C7−123.4 (3)C6—C1—C2—C3179.2 (3)
N1—Zr1—O3—C78.1 (2)C1—C2—C3—C41.1 (5)
N2—Zr1—O3—C7120.7 (2)C2—C3—C4—C5−0.2 (5)
O3—Zr1—O5—C11166.3 (3)C1—N1—C5—C40.7 (5)
O3i—Zr1—O5—C11−116.0 (3)Zr1—N1—C5—C4−179.7 (2)
O1i—Zr1—O5—C1188.4 (3)C1—N1—C5—C7−177.9 (3)
O1—Zr1—O5—C11−56.4 (3)Zr1—N1—C5—C71.7 (3)
O5i—Zr1—O5—C1115.4 (2)C3—C4—C5—N1−0.7 (5)
N1i—Zr1—O5—C11127.9 (2)C3—C4—C5—C7177.7 (3)
N1—Zr1—O5—C11−124.3 (3)Zr1—O1—C6—O2179.8 (3)
N2—Zr1—O5—C1115.4 (2)Zr1—O1—C6—C1−0.4 (4)
O3—Zr1—N1—C1175.0 (3)N1—C1—C6—O2179.8 (3)
O3i—Zr1—N1—C1−83.4 (2)C2—C1—C6—O2−0.6 (5)
O1i—Zr1—N1—C1143.0 (2)N1—C1—C6—O10.0 (4)
O1—Zr1—N1—C1−0.4 (2)C2—C1—C6—O1179.7 (3)
O5—Zr1—N1—C191.0 (2)Zr1—O3—C7—O4170.7 (2)
O5i—Zr1—N1—C1−43.3 (3)Zr1—O3—C7—C5−9.9 (4)
N1i—Zr1—N1—C1−133.3 (3)N1—C5—C7—O4−176.1 (3)
N2—Zr1—N1—C146.7 (3)C4—C5—C7—O45.4 (5)
O3—Zr1—N1—C5−4.5 (2)N1—C5—C7—O34.5 (4)
O3i—Zr1—N1—C597.1 (2)C4—C5—C7—O3−174.0 (3)
O1i—Zr1—N1—C5−36.6 (3)C8i—N2—C8—C90.9 (2)
O1—Zr1—N1—C5−180.0 (3)Zr1—N2—C8—C9−179.1 (2)
O5—Zr1—N1—C5−88.5 (2)C8i—N2—C8—C11−178.4 (3)
O5i—Zr1—N1—C5137.1 (2)Zr1—N2—C8—C111.6 (3)
N1i—Zr1—N1—C547.2 (2)N2—C8—C9—C10−1.8 (5)
N2—Zr1—N1—C5−132.8 (2)C11—C8—C9—C10177.4 (3)
O3—Zr1—N2—C8−49.04 (17)C8—C9—C10—C9i0.9 (2)
O3i—Zr1—N2—C8130.96 (17)Zr1—O5—C11—O6160.2 (3)
O1i—Zr1—N2—C8−96.28 (17)Zr1—O5—C11—C8−19.8 (4)
O1—Zr1—N2—C883.72 (17)N2—C8—C11—O6−169.6 (3)
O5—Zr1—N2—C8−7.83 (17)C9—C8—C11—O611.1 (5)
O5i—Zr1—N2—C8172.17 (17)N2—C8—C11—O510.4 (4)
N1i—Zr1—N2—C8−141.88 (17)C9—C8—C11—O5−168.9 (3)
N1—Zr1—N2—C838.12 (17)
Symmetry code: (i) −x+1, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3NA···O10.772.233.003 (4)175
N3—H3NB···O2Wi0.862.152.930 (4)150
N4—H4NA···O2Wi0.832.042.818 (4)156
N4—H4NB···O1Wii0.782.062.834 (4)175
N5—H5NA···O20.881.952.828 (4)171
N5—H5NB···O3iii0.792.453.143 (4)148
N5—H5NB···O4iii0.792.523.171 (4)141
O1W—H1WA···O3iv0.842.333.041 (3)143
O1W—H1WA···O5iv0.842.383.076 (3)140
O1W—H1WB···O60.891.872.761 (3)175
O2W—H2WA···O5iv0.862.072.909 (3)165
O2W—H2WA···O6iv0.862.573.085 (3)119
O2W—H2WB···O4v0.941.842.745 (3)160
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x−1/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z; (v) x, y−1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3NA···O10.772.233.003 (4)175
N3—H3NB···O2Wi0.862.152.930 (4)150
N4—H4NA···O2Wi0.832.042.818 (4)156
N4—H4NB···O1Wii0.782.062.834 (4)175
N5—H5NA···O20.881.952.828 (4)171
N5—H5NB···O3iii0.792.453.143 (4)148
N5—H5NB···O4iii0.792.523.171 (4)141
O1W—H1WA···O3iv0.842.333.041 (3)143
O1W—H1WA···O5iv0.842.383.076 (3)140
O1W—H1WB···O60.891.872.761 (3)175
O2W—H2WA···O5iv0.862.072.909 (3)165
O2W—H2WA···O6iv0.862.573.085 (3)119
O2W—H2WB···O4v0.941.842.745 (3)160
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x−1/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z; (v) x, y−1, z.
Acknowledgements top

The authors wish to express their deepest appreciation to the late Professor Dr. H Aghabozorg who has inspired, advised and assisted during this study.

references
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