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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1670.
Published online 2010 June 16. doi:  10.1107/S1600536810022221
PMCID: PMC3006838

N′-(4-Cyano­benzyl­idene)furan-2-carbohydrazide monohydrate

Abstract

In the title compound, C13H9N3O2·H2O, the dihedral angle between the aromatic rings is 10.7 (4)° and an intra­molecular N—H(...)O hydrogen bond occurs. In the crystal, the components are linked by N—H(...)O, O—H(...)N and O—H(...)O hydrogen bonds.

Related literature

For a related structure and background references, see: Li et al. (2010 [triangle]).

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Object name is e-66-o1670-scheme1.jpg

Experimental

Crystal data

  • C13H9N3O2·H2O
  • M r = 257.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1670-efi1.jpg
  • a = 7.0501 (14) Å
  • b = 14.295 (3) Å
  • c = 12.640 (3) Å
  • β = 103.38 (3)°
  • V = 1239.3 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 11389 measured reflections
  • 2834 independent reflections
  • 1568 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.135
  • S = 0.98
  • 2834 reflections
  • 180 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.16 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/S1600536810022221/hb5490sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022221/hb5490Isup2.hkl

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

supplementary crystallographic information

Experimental

A mixture of 4-formylbenzonitrile (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 (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=0.97 Å, and with Uiso=1.2–1.5Ueq.

Figures

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

Crystal data

C13H9N3O2·H2OF(000) = 536
Mr = 257.25Dx = 1.379 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1568 reflections
a = 7.0501 (14) Åθ = 2.7–25.5°
b = 14.295 (3) ŵ = 0.10 mm1
c = 12.640 (3) ÅT = 293 K
β = 103.38 (3)°Block, colorless
V = 1239.3 (4) Å30.22 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer1568 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
graphiteθmax = 27.5°, θmin = 3.3°
[var phi] and ω scansh = −8→9
11389 measured reflectionsk = −18→18
2834 independent reflectionsl = −16→16

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.0694P)2] where P = (Fo2 + 2Fc2)/3
2834 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.16 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
N20.2572 (2)0.42473 (10)0.51829 (12)0.0431 (4)
N10.2142 (2)0.34390 (9)0.45997 (12)0.0440 (4)
H1A0.17040.34580.39060.053*
O10.10154 (18)0.19128 (9)0.33670 (10)0.0526 (4)
C60.2239 (3)0.50009 (12)0.46228 (15)0.0461 (5)
H6A0.17470.49640.38750.055*
C40.1844 (3)0.17816 (13)0.44486 (15)0.0442 (5)
O30.0883 (2)0.37589 (11)0.22607 (12)0.0654 (5)
C130.3865 (3)0.85907 (14)0.65549 (17)0.0548 (5)
O20.3075 (2)0.25365 (9)0.61179 (11)0.0595 (4)
C120.3138 (3)0.60216 (13)0.62661 (16)0.0525 (5)
H12A0.32180.54970.67090.063*
C70.2620 (3)0.59186 (12)0.51417 (15)0.0420 (4)
C50.2414 (3)0.26093 (12)0.51272 (15)0.0436 (4)
C80.2453 (3)0.67132 (13)0.44979 (16)0.0518 (5)
H8A0.20690.66550.37460.062*
C110.3534 (3)0.68908 (13)0.67294 (16)0.0551 (5)
H11A0.38870.69520.74820.066*
C100.3405 (3)0.76786 (12)0.60708 (16)0.0453 (5)
C20.0589 (3)0.10477 (13)0.29261 (18)0.0566 (6)
H2B0.00030.09310.22000.068*
N30.4234 (3)0.93164 (12)0.69148 (17)0.0721 (6)
C10.1133 (3)0.03943 (15)0.36854 (18)0.0654 (6)
H1B0.1006−0.02490.35880.078*
C90.2850 (3)0.75903 (13)0.49571 (16)0.0521 (5)
H9A0.27410.81180.45160.062*
C30.1943 (3)0.08674 (13)0.46686 (18)0.0617 (6)
H3A0.24490.05930.53420.074*
H3B0.025 (5)0.438 (3)0.208 (3)0.156 (14)*
H3C−0.005 (4)0.337 (2)0.197 (3)0.120 (12)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N20.0504 (9)0.0360 (8)0.0404 (9)0.0034 (7)0.0056 (7)−0.0056 (7)
N10.0572 (9)0.0360 (8)0.0346 (9)0.0018 (7)0.0023 (7)−0.0016 (6)
O10.0708 (9)0.0435 (7)0.0389 (8)−0.0040 (7)0.0030 (6)0.0018 (6)
C60.0560 (11)0.0405 (10)0.0384 (11)0.0028 (9)0.0037 (8)−0.0023 (8)
C40.0466 (10)0.0473 (11)0.0366 (11)0.0005 (9)0.0052 (8)0.0017 (8)
O30.0897 (11)0.0468 (9)0.0497 (9)−0.0047 (9)−0.0044 (8)0.0021 (7)
C130.0600 (12)0.0438 (11)0.0576 (13)0.0031 (10)0.0073 (10)−0.0013 (10)
O20.0829 (10)0.0532 (8)0.0369 (8)0.0059 (7)0.0026 (7)0.0064 (6)
C120.0739 (14)0.0408 (10)0.0418 (11)0.0062 (10)0.0114 (10)0.0024 (8)
C70.0435 (10)0.0381 (10)0.0428 (11)0.0050 (8)0.0072 (8)−0.0002 (8)
C50.0451 (10)0.0468 (11)0.0377 (11)0.0064 (9)0.0074 (8)0.0064 (8)
C80.0653 (12)0.0467 (11)0.0392 (12)0.0028 (9)0.0038 (9)−0.0003 (8)
C110.0768 (14)0.0483 (11)0.0369 (11)0.0042 (10)0.0064 (10)−0.0036 (9)
C100.0469 (10)0.0383 (10)0.0490 (12)0.0020 (8)0.0077 (8)−0.0048 (8)
C20.0708 (14)0.0460 (11)0.0488 (12)−0.0087 (10)0.0052 (10)−0.0062 (9)
N30.0868 (14)0.0448 (11)0.0786 (14)−0.0037 (10)0.0064 (11)−0.0129 (9)
C10.0812 (15)0.0401 (11)0.0656 (15)−0.0037 (11)−0.0021 (12)−0.0018 (10)
C90.0625 (12)0.0396 (10)0.0513 (13)0.0008 (9)0.0075 (10)0.0067 (9)
C30.0757 (14)0.0430 (11)0.0575 (14)0.0020 (10)−0.0030 (11)0.0125 (9)

Geometric parameters (Å, °)

N2—C61.281 (2)C12—C111.374 (3)
N2—N11.3664 (18)C12—C71.391 (3)
N1—C51.352 (2)C12—H12A0.9300
N1—H1A0.8600C7—C81.386 (2)
O1—C21.361 (2)C8—C91.383 (2)
O1—C41.370 (2)C8—H8A0.9300
C6—C71.464 (2)C11—C101.391 (3)
C6—H6A0.9300C11—H11A0.9300
C4—C31.335 (2)C10—C91.377 (3)
C4—C51.462 (2)C2—C11.331 (3)
O3—H3B1.00 (4)C2—H2B0.9300
O3—H3C0.87 (3)C1—C31.414 (3)
C13—N31.139 (2)C1—H1B0.9300
C13—C101.445 (3)C9—H9A0.9300
O2—C51.235 (2)C3—H3A0.9300
C6—N2—N1115.07 (15)C9—C8—C7121.00 (18)
C5—N1—N2119.16 (15)C9—C8—H8A119.5
C5—N1—H1A120.4C7—C8—H8A119.5
N2—N1—H1A120.4C12—C11—C10119.89 (18)
C2—O1—C4106.68 (15)C12—C11—H11A120.1
N2—C6—C7121.01 (17)C10—C11—H11A120.1
N2—C6—H6A119.5C9—C10—C11120.09 (17)
C7—C6—H6A119.5C9—C10—C13119.90 (17)
C3—C4—O1109.38 (16)C11—C10—C13120.01 (18)
C3—C4—C5132.55 (18)C1—C2—O1110.06 (19)
O1—C4—C5118.07 (15)C1—C2—H2B125.0
H3B—O3—H3C102 (3)O1—C2—H2B125.0
N3—C13—C10178.5 (2)C2—C1—C3106.77 (19)
C11—C12—C7120.69 (17)C2—C1—H1B126.6
C11—C12—H12A119.7C3—C1—H1B126.6
C7—C12—H12A119.7C10—C9—C8119.63 (17)
C8—C7—C12118.66 (16)C10—C9—H9A120.2
C8—C7—C6119.31 (17)C8—C9—H9A120.2
C12—C7—C6122.03 (16)C4—C3—C1107.11 (19)
O2—C5—N1123.42 (16)C4—C3—H3A126.4
O2—C5—C4120.96 (16)C1—C3—H3A126.4
N1—C5—C4115.60 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.332.692 (2)106
N1—H1A···O30.862.072.920 (2)169
O3—H3B···N3i1.00 (4)1.99 (4)2.980 (2)172 (3)
O3—H3C···O2ii0.88 (3)1.98 (3)2.848 (2)171 (3)

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) 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: HB5490).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, Y.-F., Zhang, F.-G. & Jian, F.-F. (2010). Acta Cryst. E66, o1471. [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