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Acta Cryst. (2008). E64, o2123    [ doi:10.1107/S160053680803300X ]

2,4-Dihydroxybenzaldehyde 4-ethylthiosemicarbazone

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

Abstract top

The molecular conformation of the title compound, C10H13N3O2S, is stabilized by an intramolecular O-H...N hydrogen bond. Adjacent molecules are linked by O-H...O hydrogen bonds to furnish a zigzag chain.

Related literature top

For the structure of 3,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone, see: Kayed et al. (2008). [Figure caption mentions three molecules, but only one is shown and no mention is made of them in the Abstract. Please clarify]

Experimental top

4-Ethylthiosemicarbazide (1.19 g, 10 mmol) and 2,4-dihydroxybenzaldehyde (1.38 g, 10 mmol) were refluxed in ethanol (40 ml) for 6 h. Slow evaporation of the solvent yielded yellow crystals.

Refinement top

H-atoms were placed in calculated positions (C—H 0.95 Å, N—H 0.88 Å, O—H 0.85 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C,N) or U(H) set to 1.5U(O).

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. Displacement ellipsoid (Barbour, 2001) plot of the title compound at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.
2,4-Dihydroxybenzaldehyde 4-ethylthiosemicarbazone top
Crystal data top
C10H13N3O2SF(000) = 504
Mr = 239.29Dx = 1.429 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1634 reflections
a = 4.6592 (6) Åθ = 2.6–28.1°
b = 24.067 (3) ŵ = 0.28 mm−1
c = 10.047 (1) ÅT = 100 K
β = 99.060 (2)°Plate, yellow
V = 1112.5 (2) Å30.40 × 0.12 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		2517 independent reflections
Radiation source: fine-focus sealed tube1972 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −6→4
Tmin = 0.896, Tmax = 0.983k = −30→31
6303 measured reflectionsl = −13→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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3651P]
where P = (Fo2 + 2Fc2)/3
2517 reflections(Δ/σ)max = 0.001
148 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C10H13N3O2SV = 1112.5 (2) Å3
Mr = 239.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.6592 (6) ŵ = 0.28 mm−1
b = 24.067 (3) ÅT = 100 K
c = 10.047 (1) Å0.40 × 0.12 × 0.06 mm
β = 99.060 (2)°
Data collection top
Bruker SMART APEX
diffractometer		2517 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1972 reflections with I > 2σ(I)
Tmin = 0.896, Tmax = 0.983Rint = 0.028
6303 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.38 e Å−3
S = 1.08Δρmin = −0.25 e Å−3
2517 reflectionsAbsolute structure: ?
148 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.01421 (11)0.514276 (19)0.28484 (5)0.02112 (15)
O10.1480 (3)0.32859 (6)0.28304 (13)0.0240 (3)
H10.27070.35440.29080.036*
O2−0.4004 (3)0.21979 (5)0.53651 (13)0.0238 (3)
H2−0.41520.21170.61650.036*
N10.6825 (4)0.43087 (7)0.17727 (16)0.0225 (4)
H1N0.54950.40560.18450.027*
N20.6791 (3)0.44770 (6)0.40159 (15)0.0175 (3)
H2N0.73780.46660.47600.021*
N30.4854 (3)0.40468 (6)0.40248 (15)0.0169 (3)
C10.6265 (5)0.39432 (9)−0.0504 (2)0.0270 (5)
H1A0.69850.3971−0.13670.040*
H1B0.41690.4015−0.06440.040*
H1C0.66440.3569−0.01320.040*
C20.7804 (5)0.43673 (9)0.0471 (2)0.0276 (5)
H2A0.99320.43090.05780.033*
H2B0.73710.47470.01150.033*
C30.7800 (4)0.46113 (7)0.28620 (18)0.0174 (4)
C40.3905 (4)0.39384 (7)0.51361 (17)0.0162 (4)
H40.45680.41520.59200.019*
C50.1834 (4)0.34936 (7)0.51966 (18)0.0154 (4)
C60.0690 (4)0.31772 (7)0.40586 (18)0.0174 (4)
C7−0.1245 (4)0.27525 (8)0.41357 (19)0.0195 (4)
H7−0.19830.25450.33520.023*
C8−0.2121 (4)0.26265 (7)0.53563 (18)0.0179 (4)
C9−0.1092 (4)0.29412 (7)0.65039 (18)0.0181 (4)
H9−0.17290.28640.73380.022*
C100.0857 (4)0.33653 (7)0.64102 (18)0.0171 (4)
H100.15600.35770.71920.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0235 (3)0.0188 (2)0.0214 (2)−0.0054 (2)0.00430 (19)0.00073 (18)
O10.0316 (9)0.0240 (7)0.0169 (6)−0.0099 (6)0.0059 (6)−0.0026 (5)
O20.0275 (8)0.0207 (7)0.0225 (7)−0.0089 (6)0.0019 (6)0.0036 (5)
N10.0235 (9)0.0242 (8)0.0207 (8)−0.0087 (7)0.0063 (7)−0.0028 (7)
N20.0181 (8)0.0176 (8)0.0167 (7)−0.0047 (6)0.0022 (6)−0.0009 (6)
N30.0154 (8)0.0139 (7)0.0211 (8)−0.0016 (6)0.0019 (6)0.0017 (6)
C10.0302 (12)0.0283 (11)0.0228 (10)−0.0037 (9)0.0056 (9)−0.0022 (8)
C20.0301 (12)0.0332 (11)0.0209 (10)−0.0089 (10)0.0081 (9)−0.0025 (8)
C30.0141 (10)0.0168 (9)0.0209 (9)0.0029 (7)0.0017 (7)0.0019 (7)
C40.0151 (10)0.0162 (8)0.0165 (9)0.0004 (7)0.0004 (7)−0.0011 (7)
C50.0138 (9)0.0133 (8)0.0185 (9)0.0021 (7)0.0006 (7)0.0002 (7)
C60.0176 (10)0.0179 (9)0.0166 (9)0.0025 (7)0.0027 (7)0.0007 (7)
C70.0208 (10)0.0169 (9)0.0195 (9)−0.0012 (8)−0.0010 (8)−0.0014 (7)
C80.0154 (10)0.0139 (8)0.0232 (9)−0.0007 (7)−0.0005 (8)0.0031 (7)
C90.0184 (10)0.0190 (9)0.0168 (9)0.0012 (7)0.0021 (7)0.0033 (7)
C100.0180 (10)0.0170 (9)0.0155 (8)0.0015 (8)−0.0003 (7)−0.0017 (7)
Geometric parameters (Å, °) top
S1—C31.6826 (19)C1—H1C0.9800
O1—C61.367 (2)C2—H2A0.9900
O1—H10.8400C2—H2B0.9900
O2—C81.355 (2)C4—C51.449 (2)
O2—H20.8400C4—H40.9500
N1—C31.333 (2)C5—C101.401 (2)
N1—C21.458 (2)C5—C61.407 (2)
N1—H1N0.8800C6—C71.373 (3)
N2—C31.357 (2)C7—C81.386 (3)
N2—N31.374 (2)C7—H70.9500
N2—H2N0.8800C8—C91.400 (3)
N3—C41.291 (2)C9—C101.379 (3)
C1—C21.515 (3)C9—H90.9500
C1—H1A0.9800C10—H100.9500
C1—H1B0.9800
C6—O1—H1109.5N2—C3—S1120.03 (14)
C8—O2—H2109.5N3—C4—C5120.45 (16)
C3—N1—C2124.66 (16)N3—C4—H4119.8
C3—N1—H1N117.7C5—C4—H4119.8
C2—N1—H1N117.7C10—C5—C6117.04 (17)
C3—N2—N3120.08 (15)C10—C5—C4120.59 (16)
C3—N2—H2N120.0C6—C5—C4122.37 (16)
N3—N2—H2N120.0O1—C6—C7117.76 (17)
C4—N3—N2118.21 (15)O1—C6—C5120.57 (17)
C2—C1—H1A109.5C7—C6—C5121.67 (17)
C2—C1—H1B109.5C6—C7—C8120.03 (17)
H1A—C1—H1B109.5C6—C7—H7120.0
C2—C1—H1C109.5C8—C7—H7120.0
H1A—C1—H1C109.5O2—C8—C7116.98 (17)
H1B—C1—H1C109.5O2—C8—C9123.01 (17)
N1—C2—C1109.36 (17)C7—C8—C9120.00 (17)
N1—C2—H2A109.8C10—C9—C8119.21 (17)
C1—C2—H2A109.8C10—C9—H9120.4
N1—C2—H2B109.8C8—C9—H9120.4
C1—C2—H2B109.8C9—C10—C5122.00 (17)
H2A—C2—H2B108.3C9—C10—H10119.0
N1—C3—N2116.86 (17)C5—C10—H10119.0
N1—C3—S1123.11 (14)
C3—N2—N3—C4−178.76 (17)C10—C5—C6—C7−1.5 (3)
C3—N1—C2—C1178.52 (18)C4—C5—C6—C7179.20 (17)
C2—N1—C3—N2−175.78 (18)O1—C6—C7—C8−179.83 (17)
C2—N1—C3—S14.9 (3)C5—C6—C7—C80.1 (3)
N3—N2—C3—N10.0 (2)C6—C7—C8—O2−179.15 (16)
N3—N2—C3—S1179.30 (13)C6—C7—C8—C91.6 (3)
N2—N3—C4—C5179.27 (15)O2—C8—C9—C10179.01 (17)
N3—C4—C5—C10178.30 (17)C7—C8—C9—C10−1.8 (3)
N3—C4—C5—C6−2.4 (3)C8—C9—C10—C50.3 (3)
C10—C5—C6—O1178.39 (16)C6—C5—C10—C91.3 (3)
C4—C5—C6—O1−0.9 (3)C4—C5—C10—C9−179.39 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N30.841.842.583 (2)147
O2—H2···O1i0.841.922.714 (2)158
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N30.841.842.583 (2)147
O2—H2···O1i0.841.922.714 (2)158
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.
Acknowledgements top

We thank the University of Malaya for supporting this study. KWT thanks the Ministry of Higher Education for an SLAI scholarship in this research.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Kayed, S. F., Farina, Y., Baba, I. & Simpson, J. (2008). Acta Cryst. E64, o824–o825.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2008). publCIF. In preparation.