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Acta Cryst. (2008). E64, o1073    [ doi:10.1107/S160053680801386X ]

3,4-Dihydroxybenzaldehyde thiosemicarbazone

K. W. Tan, Y. Farina, C. H. Ng, M. J. Maah and S. W. Ng

Abstract top

The asymmetric unit of the title compound, C8H9N3O2S, contains three independent molecules which are stacked approximately over each other. In the crystal structure, centrosymmetric pairs of molecules are formed through intermolecular hydroxy-hydroxy O-H...O and hydroxy-sulfur O-H...S hydrogen bonds which are, in turn, linked into a two-dimensional network by N-H...O(hydroxy) hydrogen bonds.

Comment top

A previous study of Schiff bases derived by condensing substituted benzaldehydes with 4-phenylthiosemicarbazides describes the 3,4-dihydroxybenzaldehyde derivative, which crystallizes as a hemihydrate. The compound features extensive hydrogen bonds (Swesi et al., 2006). The condensation product of the reaction between thiosemicarbazide and 3,4-dihydroxybenzaldehyde has an amino –NH2 group in place of the phenyl group. In the crystal structure, a molecule is linked to an adjacent molecule by a hydrogen bond [O–H3-hydroxy···O4-hydroxy]; it is linked to another adjacent molecule by another hydrogen bond [O–H4-hydroxy···S]. The structure is consolidated into a two-dimensional network motif by a Nterminal–H···O4-hydroxy hydrogen bond. The asymmetric unit features three molecules that are approximately stacked over each other (Fig. 1).

Related literature top

For the structure of 3,4-dihydroxybenzaldehyde 4-phenylthiosemicarbazone, see: Swesi et al. (2006). For some metal complexes of the ligand, see: Zhu et al. (1991, 1997).

Experimental top

Thiosemicarbazide (0.09 g, 1 mmol) and 2,4-dihydroxybenzaldehyde (0.14 g, 1 mmol) were heated in an ethanol/water mixture (20/5 ml) for 3 h. Slow evaporation of the solvent yielded yellow crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 U(C). The amino H-atoms were similarly treated (N–H 0.88 Å). The hydroxy H-atoms were located in a difference Fourier map, and were refined with a distance retraint of O–H 0.85±0.01 Å; their temperature factors were tied by a factor of 1.5.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid (Barbour, 2001) plot of the three independent molecules of C14H13N3O2S at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.
3,4-Dihydroxybenzaldehyde thiosemicarbazone top
Crystal data top
C8H9N3O2SZ = 6
Mr = 211.24F000 = 660
Triclinic, P1Dx = 1.514 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.657 (2) ÅCell parameters from 1478 reflections
b = 11.794 (2) Åθ = 2.7–27.8º
c = 12.356 (2) ŵ = 0.33 mm−1
α = 111.657 (2)ºT = 100 (2) K
β = 104.082 (2)ºBlock, yellow
γ = 90.929 (2)º0.20 × 0.18 × 0.04 mm
V = 1390.2 (4) Å3
Data collection top
Bruker SMART APEX
diffractometer		6298 independent reflections
Radiation source: fine-focus sealed tube3727 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.938, Tmax = 0.987k = −15→9
8792 measured reflectionsl = −14→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.189  w = 1/[σ2(Fo2) + (0.1004P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6298 reflectionsΔρmax = 0.51 e Å−3
397 parametersΔρmin = −0.39 e Å−3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C8H9N3O2Sγ = 90.929 (2)º
Mr = 211.24V = 1390.2 (4) Å3
Triclinic, P1Z = 6
a = 10.657 (2) ÅMo Kα
b = 11.794 (2) ŵ = 0.33 mm−1
c = 12.356 (2) ÅT = 100 (2) K
α = 111.657 (2)º0.20 × 0.18 × 0.04 mm
β = 104.082 (2)º
Data collection top
Bruker SMART APEX
diffractometer		6298 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3727 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.987Rint = 0.028
8792 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0616 restraints
wR(F2) = 0.189H atoms treated by a mixture of
independent and constrained refinement
S = 1.01Δρmax = 0.51 e Å−3
6298 reflectionsΔρmin = −0.39 e Å−3
397 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.84547 (10)0.94314 (8)0.21803 (8)0.0401 (3)
S20.45653 (10)0.85179 (8)0.31556 (7)0.0359 (2)
S30.10237 (10)0.74686 (8)0.41416 (8)0.0390 (3)
O10.7414 (3)0.5896 (2)0.7057 (2)0.0440 (7)
H1O0.750 (4)0.566 (4)0.763 (3)0.066*
O20.7519 (2)0.7405 (2)0.9368 (2)0.0333 (6)
H2O0.769 (4)0.797 (3)1.0057 (17)0.050*
O30.4715 (4)0.5066 (2)0.8312 (2)0.0615 (9)
H3O0.476 (5)0.496 (5)0.895 (3)0.092*
O40.4659 (3)0.6536 (2)1.05646 (19)0.0359 (6)
H4O0.464 (4)0.710 (3)1.122 (2)0.054*
O50.2270 (3)0.4329 (2)0.9629 (2)0.0441 (7)
H5O0.232 (4)0.426 (4)1.029 (2)0.066*
O60.1658 (3)0.5600 (2)1.1704 (2)0.0370 (6)
H6O0.152 (4)0.609 (3)1.235 (2)0.056*
N10.7685 (3)0.7537 (3)0.2628 (2)0.0407 (8)
H1N10.74860.72100.31090.049*
H1N20.76220.70720.18680.049*
N20.8145 (3)0.9368 (2)0.4209 (2)0.0328 (7)
H2N0.83321.01720.45200.039*
N30.7922 (3)0.8755 (2)0.4912 (2)0.0316 (6)
N40.4570 (3)0.6598 (3)0.3786 (3)0.0438 (8)
H4N10.45310.62590.43050.053*
H4N20.46370.61410.30610.053*
N50.4424 (3)0.8421 (2)0.5209 (2)0.0294 (6)
H5N0.43790.92180.54600.035*
N60.4390 (3)0.7808 (2)0.5960 (2)0.0282 (6)
N70.1429 (3)0.5636 (3)0.4892 (3)0.0470 (9)
H7N10.14570.53090.54310.056*
H7N20.16070.52100.42050.056*
N80.0866 (3)0.7341 (3)0.6182 (2)0.0334 (7)
H8N0.06170.80820.63700.040*
N90.1000 (3)0.6760 (2)0.6982 (2)0.0299 (6)
C10.8075 (3)0.8720 (3)0.3043 (3)0.0300 (7)
C20.7942 (3)0.9415 (3)0.5994 (3)0.0306 (7)
H20.80721.02840.62580.037*
C30.7772 (3)0.8876 (3)0.6840 (3)0.0279 (7)
C40.7636 (3)0.7614 (3)0.6542 (3)0.0296 (7)
H40.76050.70700.57430.035*
C50.7545 (3)0.7147 (3)0.7389 (3)0.0293 (7)
C60.7597 (3)0.7934 (3)0.8565 (3)0.0257 (7)
C70.7714 (3)0.9180 (3)0.8871 (3)0.0319 (8)
H7C0.77370.97190.96700.038*
C80.7799 (3)0.9652 (3)0.8013 (3)0.0327 (8)
H80.78751.05160.82280.039*
C90.4526 (3)0.7787 (3)0.4095 (3)0.0273 (7)
C100.4204 (3)0.8443 (3)0.6983 (3)0.0288 (7)
H100.40540.92770.71640.035*
C110.4218 (3)0.7917 (3)0.7876 (3)0.0252 (7)
C120.4409 (3)0.6698 (3)0.7657 (3)0.0298 (7)
H120.44590.61640.68790.036*
C130.4526 (3)0.6261 (3)0.8557 (3)0.0321 (8)
C140.4480 (3)0.7039 (3)0.9711 (3)0.0257 (7)
C150.4243 (3)0.8234 (3)0.9921 (3)0.0316 (8)
H150.41720.87601.06940.038*
C160.4107 (3)0.8671 (3)0.9006 (3)0.0304 (7)
H160.39360.94950.91530.036*
C170.1122 (3)0.6761 (3)0.5111 (3)0.0306 (7)
C180.0760 (3)0.7363 (3)0.7984 (3)0.0286 (7)
H180.04650.81470.81200.034*
C190.0928 (3)0.6872 (3)0.8926 (3)0.0264 (7)
C200.1458 (3)0.5772 (3)0.8812 (3)0.0288 (7)
H200.16620.52950.80810.035*
C210.1686 (3)0.5376 (3)0.9745 (3)0.0291 (7)
C220.1375 (3)0.6051 (3)1.0814 (3)0.0270 (7)
C230.0804 (3)0.7116 (3)1.0922 (3)0.0295 (7)
H230.05560.75661.16370.035*
C240.0594 (3)0.7524 (3)0.9982 (3)0.0300 (7)
H240.02140.82641.00640.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0718 (7)0.0287 (5)0.0288 (5)0.0104 (4)0.0234 (4)0.0146 (4)
S20.0636 (6)0.0242 (4)0.0253 (4)0.0079 (4)0.0172 (4)0.0123 (4)
S30.0631 (6)0.0330 (5)0.0286 (5)0.0124 (4)0.0187 (4)0.0164 (4)
O10.083 (2)0.0205 (12)0.0354 (14)0.0112 (13)0.0242 (14)0.0123 (11)
O20.0527 (15)0.0269 (13)0.0263 (12)0.0067 (11)0.0144 (11)0.0144 (10)
O30.137 (3)0.0278 (15)0.0344 (15)0.0361 (17)0.0385 (18)0.0173 (13)
O40.0637 (17)0.0257 (13)0.0238 (12)0.0131 (12)0.0166 (12)0.0123 (10)
O50.083 (2)0.0266 (13)0.0343 (14)0.0200 (13)0.0278 (14)0.0167 (12)
O60.0633 (17)0.0276 (13)0.0252 (12)0.0146 (12)0.0162 (12)0.0127 (11)
N10.075 (2)0.0255 (16)0.0245 (15)0.0053 (15)0.0198 (15)0.0091 (13)
N20.0565 (19)0.0214 (14)0.0249 (14)0.0070 (13)0.0161 (13)0.0105 (12)
N30.0492 (18)0.0255 (15)0.0270 (14)0.0069 (13)0.0133 (13)0.0156 (12)
N40.085 (3)0.0232 (16)0.0285 (16)0.0122 (16)0.0230 (16)0.0106 (13)
N50.0500 (18)0.0194 (13)0.0235 (14)0.0081 (12)0.0140 (12)0.0107 (11)
N60.0444 (17)0.0221 (14)0.0230 (13)0.0032 (12)0.0105 (12)0.0131 (11)
N70.088 (3)0.0285 (17)0.0371 (17)0.0156 (17)0.0319 (17)0.0165 (14)
N80.0529 (19)0.0271 (15)0.0302 (15)0.0141 (13)0.0172 (13)0.0179 (13)
N90.0426 (17)0.0239 (14)0.0293 (14)0.0056 (12)0.0133 (12)0.0147 (12)
C10.043 (2)0.0262 (17)0.0261 (17)0.0123 (15)0.0121 (15)0.0143 (15)
C20.044 (2)0.0221 (16)0.0274 (17)0.0042 (15)0.0093 (15)0.0119 (14)
C30.0387 (19)0.0247 (17)0.0249 (16)0.0075 (14)0.0106 (14)0.0134 (14)
C40.042 (2)0.0221 (16)0.0261 (17)0.0081 (14)0.0122 (14)0.0087 (14)
C50.0412 (19)0.0190 (16)0.0316 (17)0.0082 (14)0.0128 (15)0.0119 (14)
C60.0326 (18)0.0267 (17)0.0235 (16)0.0092 (14)0.0116 (13)0.0132 (14)
C70.050 (2)0.0246 (17)0.0223 (16)0.0063 (15)0.0118 (15)0.0086 (14)
C80.049 (2)0.0179 (16)0.0316 (18)0.0037 (15)0.0121 (16)0.0094 (14)
C90.0363 (18)0.0234 (17)0.0245 (16)0.0080 (14)0.0089 (14)0.0111 (14)
C100.0357 (19)0.0256 (17)0.0293 (17)0.0079 (14)0.0114 (14)0.0137 (14)
C110.0315 (17)0.0240 (16)0.0250 (16)0.0059 (13)0.0099 (13)0.0133 (14)
C120.046 (2)0.0250 (17)0.0211 (15)0.0092 (15)0.0134 (14)0.0092 (14)
C130.050 (2)0.0209 (16)0.0306 (17)0.0120 (15)0.0156 (15)0.0126 (14)
C140.0371 (18)0.0245 (16)0.0211 (15)0.0062 (14)0.0111 (13)0.0128 (13)
C150.047 (2)0.0236 (17)0.0259 (17)0.0085 (15)0.0163 (15)0.0074 (14)
C160.048 (2)0.0191 (16)0.0296 (17)0.0078 (14)0.0133 (15)0.0132 (14)
C170.0397 (19)0.0259 (17)0.0288 (17)0.0040 (15)0.0122 (15)0.0116 (15)
C180.0333 (18)0.0267 (17)0.0289 (17)0.0061 (14)0.0096 (14)0.0131 (14)
C190.0337 (18)0.0221 (16)0.0242 (16)0.0019 (13)0.0079 (13)0.0098 (13)
C200.042 (2)0.0212 (16)0.0262 (16)0.0048 (14)0.0140 (14)0.0094 (14)
C210.0408 (19)0.0205 (16)0.0300 (17)0.0070 (14)0.0141 (14)0.0111 (14)
C220.0361 (18)0.0240 (16)0.0242 (16)0.0036 (14)0.0103 (14)0.0115 (14)
C230.0405 (19)0.0252 (17)0.0245 (16)0.0092 (15)0.0131 (14)0.0084 (14)
C240.0375 (19)0.0248 (17)0.0281 (17)0.0067 (14)0.0089 (14)0.0103 (14)
Geometric parameters (Å, °) top
S1—C11.693 (3)N9—C181.270 (4)
S2—C91.689 (3)C2—C31.453 (4)
S3—C171.680 (3)C2—H20.9500
O1—C51.372 (4)C3—C41.391 (4)
O1—H1O0.837 (10)C3—C81.393 (4)
O2—C61.369 (4)C4—C51.372 (4)
O2—H2O0.840 (10)C4—H40.9500
O3—C131.358 (4)C5—C61.392 (4)
O3—H3O0.836 (10)C6—C71.371 (4)
O4—C141.367 (4)C7—C81.387 (4)
O4—H4O0.841 (10)C7—H7C0.9500
O5—C211.368 (4)C8—H80.9500
O5—H5O0.838 (10)C10—C111.450 (4)
O6—C221.364 (4)C10—H100.9500
O6—H6O0.844 (10)C11—C161.385 (4)
N1—C11.316 (4)C11—C121.390 (4)
N1—H1N10.8800C12—C131.369 (4)
N1—H1N20.8800C12—H120.9500
N2—C11.341 (4)C13—C141.396 (4)
N2—N31.375 (3)C14—C151.375 (4)
N2—H2N0.8800C15—C161.385 (4)
N3—C21.269 (4)C15—H150.9500
N4—C91.316 (4)C16—H160.9500
N4—H4N10.8800C18—C191.457 (4)
N4—H4N20.8800C18—H180.9500
N5—C91.335 (4)C19—C241.384 (4)
N5—N61.377 (3)C19—C201.397 (4)
N5—H5N0.8800C20—C211.368 (4)
N6—C101.276 (4)C20—H200.9500
N7—C171.316 (4)C21—C221.390 (4)
N7—H7N10.8800C22—C231.380 (4)
N7—H7N20.8800C23—C241.386 (4)
N8—C171.344 (4)C23—H230.9500
N8—N91.380 (3)C24—H240.9500
N8—H8N0.8800
C5—O1—H1O115 (3)C3—C8—H8119.6
C6—O2—H2O107 (3)N4—C9—N5116.7 (3)
C13—O3—H3O106 (4)N4—C9—S2123.5 (2)
C14—O4—H4O107 (3)N5—C9—S2119.8 (2)
C21—O5—H5O103 (3)N6—C10—C11121.2 (3)
C22—O6—H6O112 (3)N6—C10—H10119.4
C1—N1—H1N1120.0C11—C10—H10119.4
C1—N1—H1N2120.0C16—C11—C12119.0 (3)
H1N1—N1—H1N2120.0C16—C11—C10118.9 (3)
C1—N2—N3118.9 (3)C12—C11—C10122.0 (3)
C1—N2—H2N120.5C13—C12—C11120.3 (3)
N3—N2—H2N120.5C13—C12—H12119.8
C2—N3—N2116.4 (3)C11—C12—H12119.8
C9—N4—H4N1120.0O3—C13—C12118.8 (3)
C9—N4—H4N2120.0O3—C13—C14120.7 (3)
H4N1—N4—H4N2120.0C12—C13—C14120.5 (3)
C9—N5—N6118.9 (3)O4—C14—C15124.2 (3)
C9—N5—H5N120.6O4—C14—C13116.4 (3)
N6—N5—H5N120.6C15—C14—C13119.4 (3)
C10—N6—N5116.1 (3)C14—C15—C16120.0 (3)
C17—N7—H7N1120.0C14—C15—H15120.0
C17—N7—H7N2120.0C16—C15—H15120.0
H7N1—N7—H7N2120.0C15—C16—C11120.6 (3)
C17—N8—N9119.0 (3)C15—C16—H16119.7
C17—N8—H8N120.5C11—C16—H16119.7
N9—N8—H8N120.5N7—C17—N8115.9 (3)
C18—N9—N8115.9 (3)N7—C17—S3124.0 (3)
N1—C1—N2116.6 (3)N8—C17—S3120.0 (3)
N1—C1—S1123.3 (2)N9—C18—C19121.1 (3)
N2—C1—S1120.1 (2)N9—C18—H18119.5
N3—C2—C3121.7 (3)C19—C18—H18119.5
N3—C2—H2119.2C24—C19—C20118.6 (3)
C3—C2—H2119.2C24—C19—C18119.6 (3)
C4—C3—C8118.5 (3)C20—C19—C18121.8 (3)
C4—C3—C2122.7 (3)C21—C20—C19120.4 (3)
C8—C3—C2118.8 (3)C21—C20—H20119.8
C5—C4—C3120.7 (3)C19—C20—H20119.8
C5—C4—H4119.7O5—C21—C20119.0 (3)
C3—C4—H4119.7O5—C21—C22120.3 (3)
O1—C5—C4118.7 (3)C20—C21—C22120.6 (3)
O1—C5—C6121.0 (3)O6—C22—C23123.8 (3)
C4—C5—C6120.3 (3)O6—C22—C21116.6 (3)
O2—C6—C7123.0 (3)C23—C22—C21119.6 (3)
O2—C6—C5117.1 (3)C22—C23—C24119.5 (3)
C7—C6—C5119.9 (3)C22—C23—H23120.2
C6—C7—C8119.8 (3)C24—C23—H23120.2
C6—C7—H7C120.1C19—C24—C23121.2 (3)
C8—C7—H7C120.1C19—C24—H24119.4
C7—C8—C3120.8 (3)C23—C24—H24119.4
C7—C8—H8119.6
C1—N2—N3—C2−176.9 (3)C11—C12—C13—C14−1.3 (5)
C9—N5—N6—C10−175.5 (3)O3—C13—C14—O41.2 (5)
C17—N8—N9—C18179.2 (3)C12—C13—C14—O4−177.4 (3)
N3—N2—C1—N15.5 (5)O3—C13—C14—C15−177.8 (3)
N3—N2—C1—S1−175.4 (2)C12—C13—C14—C153.7 (5)
N2—N3—C2—C3−177.5 (3)O4—C14—C15—C16178.4 (3)
N3—C2—C3—C42.9 (5)C13—C14—C15—C16−2.7 (5)
N3—C2—C3—C8−179.7 (3)C14—C15—C16—C11−0.5 (5)
C8—C3—C4—C5−0.8 (5)C12—C11—C16—C152.9 (5)
C2—C3—C4—C5176.6 (3)C10—C11—C16—C15−173.6 (3)
C3—C4—C5—O1−179.9 (3)N9—N8—C17—N73.0 (5)
C3—C4—C5—C6−0.4 (5)N9—N8—C17—S3−177.6 (2)
O1—C5—C6—O20.4 (5)N8—N9—C18—C19−177.0 (3)
C4—C5—C6—O2−179.1 (3)N9—C18—C19—C24−176.7 (3)
O1—C5—C6—C7−179.3 (3)N9—C18—C19—C205.3 (5)
C4—C5—C6—C71.2 (5)C24—C19—C20—C21−2.5 (5)
O2—C6—C7—C8179.5 (3)C18—C19—C20—C21175.5 (3)
C5—C6—C7—C8−0.9 (5)C19—C20—C21—O5−176.6 (3)
C6—C7—C8—C3−0.3 (5)C19—C20—C21—C221.1 (5)
C4—C3—C8—C71.1 (5)O5—C21—C22—O6−1.2 (5)
C2—C3—C8—C7−176.4 (3)C20—C21—C22—O6−178.8 (3)
N6—N5—C9—N40.9 (5)O5—C21—C22—C23179.0 (3)
N6—N5—C9—S2179.8 (2)C20—C21—C22—C231.4 (5)
N5—N6—C10—C11−176.7 (3)O6—C22—C23—C24177.8 (3)
N6—C10—C11—C16175.3 (3)C21—C22—C23—C24−2.5 (5)
N6—C10—C11—C12−1.1 (5)C20—C19—C24—C231.4 (5)
C16—C11—C12—C13−2.0 (5)C18—C19—C24—C23−176.6 (3)
C10—C11—C12—C13174.4 (3)C22—C23—C24—C191.0 (5)
C11—C12—C13—O3−179.9 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O6i0.84 (1)2.07 (3)2.784 (3)143 (4)
O2—H2o···S1ii0.84 (1)2.47 (1)3.300 (2)171 (4)
N1—H1n2···O5iii0.882.002.856 (4)163
O3—H3o···O4i0.84 (1)2.11 (4)2.732 (3)130 (4)
O4—H4o···S2ii0.84 (1)2.38 (1)3.219 (2)174 (4)
N4—H4n2···O3iii0.882.052.900 (4)162
O5—H5o···O2i0.84 (1)2.16 (4)2.742 (3)127 (4)
O6—H6o···S3ii0.84 (1)2.40 (1)3.244 (2)177 (4)
N7—H7n2···O1iii0.882.132.981 (4)161
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O6i0.84 (1)2.07 (3)2.784 (3)143 (4)
O2—H2o···S1ii0.84 (1)2.47 (1)3.300 (2)171 (4)
N1—H1n2···O5iii0.882.002.856 (4)163
O3—H3o···O4i0.84 (1)2.11 (4)2.732 (3)130 (4)
O4—H4o···S2ii0.84 (1)2.38 (1)3.219 (2)174 (4)
N4—H4n2···O3iii0.882.052.900 (4)162
O5—H5o···O2i0.84 (1)2.16 (4)2.742 (3)127 (4)
O6—H6o···S3ii0.84 (1)2.40 (1)3.244 (2)177 (4)
N7—H7n2···O1iii0.882.132.981 (4)161
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the University of Malaya (P0265/2007A) for supporting this study. KWT thanks the Ministry of Higher Education for a SLAI scholarship in this research.

references
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