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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2123.
Published online 2008 October 18. doi:  10.1107/S160053680803300X
PMCID: PMC2959729

2,4-Dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone

Abstract

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

For the structure of 3,4-dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone, see: Kayed et al. (2008 [triangle]).

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Object name is e-64-o2123-scheme1.jpg

Experimental

Crystal data

  • C10H13N3O2S
  • M r = 239.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2123-efi1.jpg
  • a = 4.6592 (6) Å
  • b = 24.067 (3) Å
  • c = 10.047 (1) Å
  • β = 99.060 (2)°
  • V = 1112.5 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 100 (2) K
  • 0.40 × 0.12 × 0.06 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.896, T max = 0.983
  • 6303 measured reflections
  • 2517 independent reflections
  • 1972 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.109
  • S = 1.08
  • 2517 reflections
  • 148 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.25 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803300X/bt2806sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803300X/bt2806Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya (grant No. PJP F316/2008C) for supporting this study. KWT thanks the Ministry of Higher Education for an SLAI scholarship in this research.

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

C10H13N3O2SF(000) = 504
Mr = 239.29Dx = 1.429 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer2517 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

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 = 1.08w = 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 Å3
0 restraintsΔρmin = −0.25 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2806).

References

  • 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. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography