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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o924.
Published online 2010 March 27. doi:  10.1107/S1600536810010810
PMCID: PMC2983835

N′-[(5-Methyl-2-fur­yl)methyl­ene]thio­phene-2-carbohydrazide

Abstract

In the title compound, C11H10N2O2S, the dihedral angle between the five-membered aromatic rings is 10.24 (12)°. In the crystal structure, mol­ecules are linked by bifurcated N—H(...)(O,N) hydrogen bonds, generating [001] chains.

Related literature

For related structures, see: Jiang (2010a [triangle],b [triangle]).

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Object name is e-66-0o924-scheme1.jpg

Experimental

Crystal data

  • C11H10N2O2S
  • M r = 234.27
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-66-0o924-efi1.jpg
  • a = 8.8037 (12) Å
  • c = 14.670 (3) Å
  • V = 1137.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.19 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 10087 measured reflections
  • 2597 independent reflections
  • 2073 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.087
  • S = 0.96
  • 2597 reflections
  • 145 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.14 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1241 Friedel pairs
  • Flack parameter: −0.11 (8)

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010810/hb5367sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010810/hb5367Isup2.hkl

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

supplementary crystallographic information

Comment

As part of our ongoing studies of Schiff bases (Jiang, 2010a,b), we have synthesized the title compound (I), and describe its structure here, which occurs in the unusual enantiomorphous space group of P43.

The molcular structure of (I) is shown in Fig. 1. In the crystal, the molecules are linked by bifurcated N—H···(O,N) hydrogen bonds (Table 1).

Experimental

A mixture of thiophene-2-carbohydrazide (0.05 mol) and 5-methylfuran-2-carbaldehyde (0.05 mol) was stirred in refluxing ethanol (10 ml) for 4 h to afford the title compound (0.082 mol, yield 82%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93-0.97 Å; N—H = 0.86Å and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C11H10N2O2SDx = 1.369 Mg m3
Mr = 234.27Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 2073 reflections
Hall symbol: P 4cwθ = 3.3–27.5°
a = 8.8037 (12) ŵ = 0.27 mm1
c = 14.670 (3) ÅT = 293 K
V = 1137.0 (3) Å3Block, colorless
Z = 40.25 × 0.20 × 0.19 mm
F(000) = 488

Data collection

Bruker SMART CCD diffractometer2073 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
graphiteθmax = 27.5°, θmin = 3.3°
ω scansh = −11→11
10087 measured reflectionsk = −11→11
2597 independent reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.087w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
2597 reflectionsΔρmax = 0.23 e Å3
145 parametersΔρmin = −0.14 e Å3
1 restraintAbsolute structure: Flack (1983), 1241 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.11 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
S10.12336 (7)0.93062 (7)0.06580 (4)0.06358 (19)
N10.44476 (18)0.45913 (18)0.09498 (10)0.0431 (4)
O20.51869 (17)0.17921 (15)0.03236 (10)0.0504 (4)
N20.40630 (18)0.59910 (17)0.12954 (10)0.0428 (4)
H2A0.44380.63130.18010.051*
C70.3074 (2)0.6842 (2)0.08110 (12)0.0403 (4)
O10.25704 (18)0.64188 (17)0.00679 (10)0.0630 (4)
C80.2645 (2)0.8314 (2)0.12060 (13)0.0407 (4)
C50.5748 (2)0.2280 (2)0.11433 (13)0.0482 (5)
C60.5305 (2)0.3756 (2)0.14463 (14)0.0477 (5)
H6A0.56410.41130.20080.057*
C90.3203 (2)0.9110 (2)0.19201 (13)0.0477 (4)
H9A0.39770.87580.22960.057*
C110.1410 (3)1.0764 (2)0.14106 (17)0.0620 (6)
H11A0.08171.16380.13920.074*
C40.6643 (3)0.1185 (3)0.15086 (18)0.0607 (6)
H4A0.71620.12320.20600.073*
C20.5746 (2)0.0350 (2)0.01820 (16)0.0545 (5)
C30.6633 (3)−0.0049 (3)0.08834 (18)0.0658 (7)
H3A0.7148−0.09650.09500.079*
C100.2494 (3)1.0520 (2)0.20326 (15)0.0561 (5)
H10A0.27471.12090.24880.067*
C10.5204 (3)−0.0399 (3)−0.06593 (18)0.0742 (7)
H1B0.5641−0.1396−0.07030.111*
H1C0.55010.0192−0.11790.111*
H1D0.4117−0.0481−0.06420.111*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0735 (4)0.0617 (3)0.0555 (3)0.0211 (3)−0.0203 (3)−0.0078 (3)
N10.0509 (9)0.0432 (9)0.0352 (8)0.0052 (7)0.0015 (6)−0.0014 (6)
O20.0607 (9)0.0452 (8)0.0451 (8)0.0124 (6)0.0076 (6)0.0052 (6)
N20.0528 (9)0.0439 (8)0.0316 (8)0.0086 (6)−0.0065 (7)−0.0071 (6)
C70.0423 (10)0.0458 (10)0.0328 (10)0.0000 (7)−0.0028 (7)−0.0029 (7)
O10.0864 (11)0.0568 (9)0.0458 (8)0.0139 (8)−0.0277 (8)−0.0164 (7)
C80.0430 (10)0.0447 (10)0.0344 (9)0.0018 (8)−0.0003 (7)−0.0019 (8)
C50.0488 (11)0.0557 (12)0.0401 (11)0.0075 (9)0.0064 (8)0.0099 (9)
C60.0494 (11)0.0554 (12)0.0384 (10)0.0056 (9)0.0010 (8)0.0014 (8)
C90.0505 (11)0.0524 (11)0.0402 (10)0.0018 (9)−0.0021 (8)−0.0080 (8)
C110.0805 (16)0.0496 (13)0.0559 (14)0.0165 (11)0.0038 (12)−0.0033 (10)
C40.0579 (13)0.0622 (14)0.0622 (14)0.0138 (10)−0.0010 (11)0.0177 (11)
C20.0635 (13)0.0409 (11)0.0591 (14)0.0078 (9)0.0238 (11)0.0076 (9)
C30.0685 (14)0.0488 (13)0.0800 (18)0.0203 (11)0.0183 (12)0.0207 (12)
C100.0690 (14)0.0488 (12)0.0506 (13)−0.0005 (10)0.0065 (11)−0.0127 (9)
C10.0939 (19)0.0570 (14)0.0716 (18)0.0044 (13)0.0229 (14)−0.0038 (12)

Geometric parameters (Å, °)

S1—C111.700 (2)C9—C101.399 (3)
S1—C81.7187 (19)C9—H9A0.9300
N1—C61.281 (3)C11—C101.338 (3)
N1—N21.375 (2)C11—H11A0.9300
O2—C51.369 (2)C4—C31.422 (4)
O2—C21.377 (2)C4—H4A0.9300
N2—C71.350 (2)C2—C31.339 (3)
N2—H2A0.8600C2—C11.479 (3)
C7—O11.234 (2)C3—H3A0.9300
C7—C81.469 (2)C10—H10A0.9300
C8—C91.353 (3)C1—H1B0.9600
C5—C41.356 (3)C1—H1C0.9600
C5—C61.428 (3)C1—H1D0.9600
C6—H6A0.9300
C11—S1—C890.80 (11)C10—C11—S1112.76 (17)
C6—N1—N2116.74 (16)C10—C11—H11A123.6
C5—O2—C2107.03 (16)S1—C11—H11A123.6
C7—N2—N1117.51 (15)C5—C4—C3106.5 (2)
C7—N2—H2A121.2C5—C4—H4A126.7
N1—N2—H2A121.2C3—C4—H4A126.7
O1—C7—N2121.93 (17)C3—C2—O2109.6 (2)
O1—C7—C8121.47 (16)C3—C2—C1135.5 (2)
N2—C7—C8116.59 (15)O2—C2—C1114.9 (2)
C9—C8—C7132.01 (18)C2—C3—C4107.37 (19)
C9—C8—S1111.17 (15)C2—C3—H3A126.3
C7—C8—S1116.74 (13)C4—C3—H3A126.3
C4—C5—O2109.5 (2)C11—C10—C9112.36 (19)
C4—C5—C6133.1 (2)C11—C10—H10A123.8
O2—C5—C6117.43 (17)C9—C10—H10A123.8
N1—C6—C5120.43 (19)C2—C1—H1B109.5
N1—C6—H6A119.8C2—C1—H1C109.5
C5—C6—H6A119.8H1B—C1—H1C109.5
C8—C9—C10112.89 (19)C2—C1—H1D109.5
C8—C9—H9A123.6H1B—C1—H1D109.5
C10—C9—H9A123.6H1C—C1—H1D109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.303.064 (2)149
N2—H2A···N1i0.862.513.218 (2)140

Symmetry codes: (i) y, −x+1, z+1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5367).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Jiang, J.-H. (2010a). Acta Cryst. E66, o922. [PMC free article] [PubMed]
  • Jiang, J.-H. (2010b). Acta Cryst. E66, o923. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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