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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2157.
Published online 2010 July 31. doi:  10.1107/S1600536810028655
PMCID: PMC3007322

(E)-N′-[4-(Methyl­sulfan­yl)benzyl­idene]furan-2-carbohydrazide monohydrate

Abstract

In the title compound, C13H12N2O2S·H2O, the dihedral angle between the aromatic rings is 35.34 (19)° and an intra­molecular N—H(...)O hydrogen bond generates an S(5) ring. In the crystal, mol­ecules are linked by N—H(...)O and O—H(...)O hydrogen bonds, generating (001) sheets.

Related literature

For a related structure, see: Li & Jian (2010 [triangle]).

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Object name is e-66-o2157-scheme1.jpg

Experimental

Crystal data

  • C13H12N2O2S·H2O
  • M r = 278.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2157-efi1.jpg
  • a = 4.7065 (9) Å
  • b = 12.142 (2) Å
  • c = 23.979 (5) Å
  • β = 91.96 (3)°
  • V = 1369.6 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 10766 measured reflections
  • 2536 independent reflections
  • 1095 reflections with I > 2σ(I)
  • R int = 0.093

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.172
  • S = 0.81
  • 2536 reflections
  • 180 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.25 e Å−3

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/S1600536810028655/hb5554sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028655/hb5554Isup2.hkl

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

supplementary crystallographic information

Experimental

A mixture of 4-(methylthio)benzaldehyde (0.1 mol), and furan-2-carbohydrazide (0.1 mol) was stirred in refluxing ethanol (20 ml) for 2 h to afford the title compound (0.090 mol, yield 90%). Colourless blocks of the title compound 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 = 0.97 Å, and Uiso = 1.2–1.5Ueq.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids.

Crystal data

C13H14N2O3SF(000) = 584
Mr = 278.32Dx = 1.350 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1095 reflections
a = 4.7065 (9) Åθ = 3.1–25.5°
b = 12.142 (2) ŵ = 0.24 mm1
c = 23.979 (5) ÅT = 293 K
β = 91.96 (3)°Block, colorless
V = 1369.6 (5) Å30.22 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer1095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.093
graphiteθmax = 25.5°, θmin = 3.1°
phi and ω scansh = −5→5
10766 measured reflectionsk = −14→14
2536 independent reflectionsl = −27→29

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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H atoms treated by a mixture of independent and constrained refinement
S = 0.81w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2536 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

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)

xyzUiso*/Ueq
C50.1858 (6)0.6495 (3)0.26977 (12)0.0476 (8)
N20.5006 (6)0.6551 (2)0.19538 (11)0.0543 (7)
C4−0.0079 (6)0.5827 (3)0.30142 (12)0.0469 (8)
O2−0.0668 (5)0.47801 (18)0.28399 (9)0.0576 (7)
C60.6577 (7)0.5956 (3)0.16494 (13)0.0544 (9)
H6A0.66640.52000.17090.065*
C1−0.3067 (8)0.5097 (3)0.35996 (15)0.0695 (11)
H1A−0.42580.50030.38980.083*
C2−0.2512 (7)0.4347 (3)0.32055 (14)0.0647 (10)
H2B−0.32730.36410.31860.078*
C81.0074 (7)0.5792 (3)0.09165 (14)0.0686 (11)
H8A1.03430.50600.10200.082*
C3−0.1508 (8)0.6049 (3)0.34769 (14)0.0620 (10)
H3A−0.14730.67050.36770.074*
O10.2107 (5)0.7491 (2)0.27923 (10)0.0628 (7)
C70.8238 (7)0.6447 (3)0.12095 (12)0.0541 (9)
N10.3328 (5)0.5959 (2)0.23110 (10)0.0512 (7)
H1B0.32270.52540.22850.061*
C120.7927 (8)0.7535 (3)0.10515 (17)0.0740 (11)
H12A0.67320.79940.12470.089*
C110.9370 (9)0.7947 (4)0.06065 (17)0.0823 (12)
H11A0.91370.86820.05070.099*
C101.1155 (8)0.7288 (4)0.03055 (16)0.0765 (12)
C91.1526 (8)0.6220 (4)0.04680 (16)0.0809 (13)
H9A1.27640.57710.02770.097*
O30.7049 (8)0.8706 (2)0.30372 (13)0.0682 (8)
S11.2735 (3)0.79024 (15)−0.02691 (5)0.1234 (7)
C131.4598 (13)0.6810 (6)−0.0588 (2)0.161 (3)
H13A1.55310.7084−0.09100.241*
H13B1.32800.6242−0.07000.241*
H13C1.59890.6515−0.03270.241*
H3B0.857 (12)0.841 (4)0.2908 (19)0.12 (2)*
H3C0.602 (17)0.833 (7)0.288 (3)0.21 (4)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C50.0404 (18)0.047 (2)0.056 (2)0.0052 (17)0.0024 (15)0.0034 (17)
N20.0518 (16)0.0511 (18)0.0606 (17)−0.0064 (15)0.0103 (14)0.0021 (14)
C40.0471 (18)0.041 (2)0.0529 (18)0.0025 (16)0.0030 (15)−0.0020 (15)
O20.0659 (14)0.0447 (14)0.0631 (14)−0.0051 (12)0.0166 (12)−0.0027 (11)
C60.0518 (19)0.052 (2)0.059 (2)−0.0016 (17)0.0055 (17)−0.0022 (17)
C10.082 (3)0.063 (3)0.065 (2)0.002 (2)0.023 (2)0.007 (2)
C20.077 (3)0.053 (2)0.065 (2)−0.011 (2)0.021 (2)0.0118 (19)
C80.060 (2)0.080 (3)0.066 (2)−0.004 (2)0.0084 (19)−0.004 (2)
C30.069 (2)0.055 (2)0.062 (2)0.0013 (19)0.0133 (19)−0.0036 (18)
O10.0614 (15)0.0406 (15)0.0878 (17)−0.0035 (12)0.0195 (13)−0.0062 (12)
C70.0426 (18)0.065 (3)0.055 (2)−0.0044 (18)−0.0002 (16)−0.0022 (18)
N10.0509 (16)0.0406 (17)0.0628 (16)−0.0010 (13)0.0091 (14)0.0006 (13)
C120.073 (3)0.066 (3)0.083 (3)−0.001 (2)0.019 (2)0.004 (2)
C110.083 (3)0.076 (3)0.089 (3)−0.011 (2)0.012 (2)0.020 (2)
C100.059 (2)0.109 (4)0.061 (2)−0.019 (3)0.0024 (19)0.009 (2)
C90.067 (3)0.109 (4)0.067 (3)−0.004 (3)0.017 (2)−0.005 (3)
O30.0683 (18)0.0448 (17)0.0929 (19)−0.0012 (15)0.0231 (17)−0.0016 (14)
S10.1001 (10)0.1929 (17)0.0779 (8)−0.0324 (10)0.0135 (7)0.0432 (9)
C130.158 (5)0.237 (8)0.092 (4)−0.087 (5)0.068 (4)−0.047 (4)

Geometric parameters (Å, °)

C5—O11.235 (4)C3—H3A0.9300
C5—N11.344 (4)C7—C121.380 (5)
C5—C41.454 (4)N1—H1B0.8600
N2—C61.280 (4)C12—C111.378 (5)
N2—N11.385 (3)C12—H12A0.9300
C4—C31.344 (4)C11—C101.381 (6)
C4—O21.364 (4)C11—H11A0.9300
O2—C21.360 (4)C10—C91.364 (6)
C6—C71.461 (4)C10—S11.754 (4)
C6—H6A0.9300C9—H9A0.9300
C1—C21.344 (5)O3—H3B0.87 (5)
C1—C31.406 (5)O3—H3C0.75 (8)
C1—H1A0.9300S1—C131.777 (6)
C2—H2B0.9300C13—H13A0.9600
C8—C71.384 (4)C13—H13B0.9600
C8—C91.394 (5)C13—H13C0.9600
C8—H8A0.9300
O1—C5—N1123.6 (3)C8—C7—C6119.4 (3)
O1—C5—C4120.5 (3)C5—N1—N2119.6 (3)
N1—C5—C4115.9 (3)C5—N1—H1B120.2
C6—N2—N1114.4 (3)N2—N1—H1B120.2
C3—C4—O2109.7 (3)C11—C12—C7120.6 (4)
C3—C4—C5131.2 (3)C11—C12—H12A119.7
O2—C4—C5119.0 (3)C7—C12—H12A119.7
C2—O2—C4106.9 (2)C12—C11—C10121.3 (4)
N2—C6—C7121.0 (3)C12—C11—H11A119.4
N2—C6—H6A119.5C10—C11—H11A119.4
C7—C6—H6A119.5C9—C10—C11118.4 (4)
C2—C1—C3107.1 (3)C9—C10—S1125.1 (4)
C2—C1—H1A126.4C11—C10—S1116.5 (4)
C3—C1—H1A126.4C10—C9—C8120.9 (4)
C1—C2—O2109.6 (3)C10—C9—H9A119.6
C1—C2—H2B125.2C8—C9—H9A119.6
O2—C2—H2B125.2H3B—O3—H3C96 (6)
C7—C8—C9120.6 (4)C10—S1—C13104.4 (3)
C7—C8—H8A119.7S1—C13—H13A109.5
C9—C8—H8A119.7S1—C13—H13B109.5
C4—C3—C1106.7 (3)H13A—C13—H13B109.5
C4—C3—H3A126.7S1—C13—H13C109.5
C1—C3—H3A126.7H13A—C13—H13C109.5
C12—C7—C8118.2 (3)H13B—C13—H13C109.5
C12—C7—C6122.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O20.862.372.713 (3)104
N1—H1B···O3i0.862.032.864 (4)162
O3—H3B···O1ii0.87 (5)2.03 (6)2.878 (4)165 (4)
O3—H3C···O10.76 (8)2.11 (8)2.800 (4)152 (8)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5554).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o2061. [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