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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2061.
Published online 2010 July 17. doi:  10.1107/S1600536810027959
PMCID: PMC3007564

N′-(3,4-Dimethyl­benzyl­idene)furan-2-carbohydrazide

Abstract

The title compound, C14H14N2O2, was prepared by the reaction of 3,4-dimethyl­benzaldehyde and furan-2-carbohydrazide. The dihedral angle between the aromatic rings is 35.48 (14)°. In the crystal, mol­ecules are linked by N—H(...)O hydrogen bonds, generating C(4) chains propagating in [010].

Related literature

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

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Object name is e-66-o2061-scheme1.jpg

Experimental

Crystal data

  • C14H14N2O2
  • M r = 242.27
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2061-efi1.jpg
  • a = 17.655 (3) Å
  • b = 7.6304 (15) Å
  • c = 19.020 (4) Å
  • V = 2562.3 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.22 × 0.21 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 21744 measured reflections
  • 2921 independent reflections
  • 1563 reflections with I > 2σ(I)
  • R int = 0.127

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.177
  • S = 0.90
  • 2921 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.21 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/S1600536810027959/hb5553sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027959/hb5553Isup2.hkl

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

supplementary crystallographic information

Experimental

A mixture of 3,4-dimethylbenzaldehyde (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%). olourless 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 molecular structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C14H14N2O2F(000) = 1024
Mr = 242.27Dx = 1.256 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1563 reflections
a = 17.655 (3) Åθ = 3.1–27.5°
b = 7.6304 (15) ŵ = 0.09 mm1
c = 19.020 (4) ÅT = 293 K
V = 2562.3 (9) Å3Block, colorless
Z = 80.22 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer1563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.127
graphiteθmax = 27.5°, θmin = 3.1°
phi and ω scansh = −22→22
21744 measured reflectionsk = −9→9
2921 independent reflectionsl = −24→23

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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2921 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.21 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
O20.34251 (10)0.2908 (2)0.40087 (10)0.0493 (5)
N20.23842 (12)0.1209 (2)0.38067 (10)0.0404 (5)
H2A0.21470.02510.38970.048*
N10.20989 (11)0.2401 (3)0.33290 (10)0.0391 (5)
C10.32632 (14)0.0301 (3)0.46664 (13)0.0393 (6)
C60.15127 (14)0.1915 (3)0.29934 (12)0.0412 (6)
H6A0.13080.08130.30790.049*
C50.30454 (14)0.1586 (3)0.41282 (12)0.0384 (6)
C70.11563 (14)0.3062 (3)0.24746 (12)0.0397 (6)
C90.11430 (15)0.5784 (3)0.18082 (13)0.0456 (7)
C40.40945 (19)−0.1050 (4)0.53228 (14)0.0580 (8)
H4A0.4554−0.14250.55080.070*
C80.14661 (15)0.4693 (3)0.23064 (13)0.0439 (7)
H8A0.19030.50580.25360.053*
C20.28720 (16)−0.0713 (3)0.51175 (13)0.0469 (7)
H2B0.2348−0.08190.51470.056*
C120.04994 (14)0.2541 (3)0.21381 (12)0.0441 (7)
H12A0.02770.14720.22490.053*
C110.01738 (15)0.3619 (4)0.16343 (13)0.0475 (7)
H11A−0.02650.32520.14070.057*
C30.34193 (18)−0.1595 (4)0.55411 (14)0.0532 (7)
H3A0.3323−0.23940.58990.064*
C140.1495 (2)0.7546 (4)0.16590 (19)0.0728 (10)
H14A0.19400.76910.19440.109*
H14B0.11380.84550.17670.109*
H14C0.16320.76140.11710.109*
C130.01177 (19)0.6353 (4)0.09024 (15)0.0709 (9)
H13A−0.03250.57710.07240.106*
H13B0.04700.65430.05250.106*
H13C−0.00250.74590.11030.106*
O10.40208 (10)0.0140 (3)0.47873 (9)0.0542 (6)
C100.04847 (15)0.5226 (4)0.14611 (12)0.0459 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0437 (11)0.0356 (10)0.0687 (12)−0.0029 (9)0.0024 (8)0.0115 (9)
N20.0499 (14)0.0268 (11)0.0444 (12)−0.0013 (10)−0.0043 (10)0.0097 (9)
N10.0449 (13)0.0310 (12)0.0414 (12)0.0036 (10)−0.0041 (10)0.0055 (9)
C10.0420 (15)0.0323 (14)0.0437 (14)0.0024 (12)−0.0047 (11)−0.0028 (10)
C60.0483 (16)0.0307 (14)0.0446 (15)−0.0021 (12)0.0013 (12)0.0039 (11)
C50.0420 (15)0.0307 (14)0.0424 (14)0.0062 (12)0.0032 (11)−0.0005 (11)
C70.0424 (15)0.0371 (15)0.0395 (13)0.0048 (11)0.0014 (11)0.0012 (11)
C90.0524 (17)0.0404 (16)0.0439 (14)0.0035 (13)0.0026 (12)0.0060 (11)
C40.064 (2)0.059 (2)0.0503 (16)0.0179 (17)−0.0090 (14)0.0095 (14)
C80.0466 (16)0.0403 (16)0.0448 (15)0.0000 (13)−0.0052 (12)0.0042 (11)
C20.0533 (17)0.0425 (16)0.0450 (15)−0.0056 (13)−0.0088 (12)0.0069 (12)
C120.0444 (16)0.0435 (16)0.0444 (15)−0.0036 (13)0.0012 (12)−0.0010 (11)
C110.0379 (15)0.0606 (19)0.0440 (14)0.0055 (14)−0.0016 (11)−0.0060 (13)
C30.068 (2)0.0452 (17)0.0461 (16)0.0005 (15)−0.0108 (14)0.0060 (13)
C140.084 (2)0.050 (2)0.085 (2)−0.0049 (18)−0.0098 (18)0.0256 (16)
C130.071 (2)0.085 (2)0.0564 (17)0.0207 (19)−0.0098 (16)0.0175 (16)
O10.0446 (11)0.0575 (13)0.0604 (12)0.0110 (10)−0.0020 (9)0.0143 (9)
C100.0486 (16)0.0547 (18)0.0345 (13)0.0138 (14)0.0026 (11)0.0035 (12)

Geometric parameters (Å, °)

O2—C51.232 (3)C4—H4A0.9300
N2—C51.349 (3)C8—H8A0.9300
N2—N11.381 (3)C2—C31.427 (4)
N2—H2A0.8600C2—H2B0.9300
N1—C61.271 (3)C12—C111.388 (4)
C1—C21.346 (4)C12—H12A0.9300
C1—O11.363 (3)C11—C101.383 (4)
C1—C51.469 (3)C11—H11A0.9300
C6—C71.462 (3)C3—H3A0.9300
C6—H6A0.9300C14—H14A0.9600
C7—C121.383 (3)C14—H14B0.9600
C7—C81.396 (4)C14—H14C0.9600
C9—C81.384 (3)C13—C101.513 (4)
C9—C101.403 (4)C13—H13A0.9600
C9—C141.508 (4)C13—H13B0.9600
C4—C31.329 (4)C13—H13C0.9600
C4—O11.371 (3)
C5—N2—N1118.3 (2)C3—C2—H2B126.8
C5—N2—H2A120.9C7—C12—C11119.8 (2)
N1—N2—H2A120.9C7—C12—H12A120.1
C6—N1—N2115.8 (2)C11—C12—H12A120.1
C2—C1—O1110.1 (2)C10—C11—C12121.7 (3)
C2—C1—C5133.9 (2)C10—C11—H11A119.1
O1—C1—C5115.8 (2)C12—C11—H11A119.1
N1—C6—C7121.0 (2)C4—C3—C2106.5 (3)
N1—C6—H6A119.5C4—C3—H3A126.8
C7—C6—H6A119.5C2—C3—H3A126.8
O2—C5—N2124.2 (2)C9—C14—H14A109.5
O2—C5—C1122.2 (2)C9—C14—H14B109.5
N2—C5—C1113.6 (2)H14A—C14—H14B109.5
C12—C7—C8118.6 (2)C9—C14—H14C109.5
C12—C7—C6120.1 (2)H14A—C14—H14C109.5
C8—C7—C6121.3 (2)H14B—C14—H14C109.5
C8—C9—C10118.7 (2)C10—C13—H13A109.5
C8—C9—C14119.7 (3)C10—C13—H13B109.5
C10—C9—C14121.6 (2)H13A—C13—H13B109.5
C3—C4—O1110.8 (3)C10—C13—H13C109.5
C3—C4—H4A124.6H13A—C13—H13C109.5
O1—C4—H4A124.6H13B—C13—H13C109.5
C9—C8—C7122.1 (2)C1—O1—C4106.2 (2)
C9—C8—H8A118.9C11—C10—C9119.1 (2)
C7—C8—H8A118.9C11—C10—C13120.1 (3)
C1—C2—C3106.5 (3)C9—C10—C13120.9 (3)
C1—C2—H2B126.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.062.921 (3)174

Symmetry codes: (i) −x+1/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5553).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1720. [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