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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2935.
Published online 2009 October 31. doi:  10.1107/S1600536809044602
PMCID: PMC2971139

Ethyl 3-[1-(2-hydroxy­phen­yl)eth­ylidene]carbazate

Abstract

The title compound, C11H14N2O3, was prepared by the reaction of ethyl carbazate and 1-(2-hydroxy­phen­yl)ethanone. In the crystal structure, mol­ecules are linked by inter­molecular N—H(...)O hydrogen bonds, forming centrosymmetric dimers. An intra­molecular O—H(...)N inter­action also occurs.

Related literature

For the applications of Schiff base compounds, see: Cimerman et al. (1997 [triangle]); Forthe C=N double-bond length in a related structure, see: Girgis (2006 [triangle]).

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Object name is e-65-o2935-scheme1.jpg

Experimental

Crystal data

  • C11H14N2O3
  • M r = 222.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2935-efi1.jpg
  • a = 5.4830 (11) Å
  • b = 10.191 (2) Å
  • c = 11.410 (2) Å
  • α = 112.53 (3)°
  • β = 95.79 (3)°
  • γ = 99.68 (3)°
  • V = 570.9 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.491, T max = 0.728
  • 5650 measured reflections
  • 2597 independent reflections
  • 1839 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.180
  • S = 1.08
  • 2597 reflections
  • 166 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.23 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/S1600536809044602/lh2935sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044602/lh2935Isup2.hkl

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

Acknowledgments

The authors would like to thank the Science Foundation of WeiFang University (No. 2009Z24).

supplementary crystallographic information

Comment

Schiff bases have received considerable attention in the literature and have potential analytical applications (Cimerman et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and its crystal structure is determined herein.

The molecular structure of (I) is shown in Fig. 1. The C7—N1 bond length of 1.2836 (18)Å is comparable with C—N double bond [1.281 (2) Å] reported (Girgis, 2006). In the crystal structure, molecules are linked by intermolecular N—H···O hydrogen bonds to form centrosymmetric dimers.

Experimental

A mixture of the 1-(2-hydroxyphenyl)ethanone (0.1 mol), and Ethyl carbazate (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.082 mol, yield 82%). Single crystals suitable for X-ray measurements were obtained by recrystallization of (I) from ethanol at room temperature.

Refinement

H atoms bonded to the O atom, the N atom and those bonded to C8 were refined independently with isotropic displacement parameters. All other H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93–0.97 Å Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C11H14N2O3Z = 2
Mr = 222.24F(000) = 236
Triclinic, P1Dx = 1.293 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4830 (11) ÅCell parameters from 1974 reflections
b = 10.191 (2) Åθ = 3.5–27.5°
c = 11.410 (2) ŵ = 0.10 mm1
α = 112.53 (3)°T = 293 K
β = 95.79 (3)°Block, colorless
γ = 99.68 (3)°0.22 × 0.20 × 0.18 mm
V = 570.9 (2) Å3

Data collection

Bruker SMART CCD diffractometer2597 independent reflections
Radiation source: fine-focus sealed tube1839 reflections with I > 2σ(I)
graphiteRint = 0.016
[var phi] and ω scansθmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→6
Tmin = 0.491, Tmax = 0.728k = −13→13
5650 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.180w = 1/[σ2(Fo2) + (0.1217P)2 + 0.0113P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
2597 reflectionsΔρmax = 0.23 e Å3
166 parametersΔρmin = −0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.043 (14)

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
O30.4674 (2)0.34070 (13)0.74631 (11)0.0681 (4)
O10.2984 (2)0.09910 (13)1.08787 (10)0.0676 (4)
O20.52301 (18)0.24189 (11)1.00894 (9)0.0549 (3)
N10.1757 (2)0.16596 (12)0.81259 (10)0.0476 (3)
N20.1444 (2)0.10360 (14)0.89965 (11)0.0536 (3)
C10.0453 (2)0.20676 (14)0.63011 (12)0.0453 (3)
C90.3238 (3)0.14591 (16)1.00535 (13)0.0505 (4)
C7−0.0055 (2)0.13722 (14)0.71973 (12)0.0440 (3)
C30.3121 (3)0.36489 (19)0.55821 (16)0.0682 (5)
H3B0.46530.42730.56900.082*
C20.2752 (3)0.30312 (15)0.64688 (14)0.0512 (4)
C100.7203 (3)0.29608 (19)1.12246 (15)0.0635 (4)
H10A0.79120.21691.12740.076*
H10B0.65260.33961.20020.076*
C8−0.2561 (3)0.0382 (2)0.69869 (19)0.0638 (5)
C5−0.0996 (4)0.2415 (2)0.43765 (17)0.0728 (5)
H5A−0.22540.22020.36770.087*
C6−0.1370 (3)0.17999 (19)0.52442 (16)0.0626 (4)
H6A−0.29120.11760.51200.075*
C40.1279 (4)0.3354 (2)0.45604 (17)0.0737 (5)
H4A0.15550.37870.39870.088*
C110.9167 (3)0.40714 (19)1.10931 (17)0.0706 (5)
H11A1.05030.44581.18290.106*
H11B0.84410.48461.10430.106*
H11C0.98250.36261.03230.106*
H3A0.407 (5)0.283 (3)0.794 (2)0.107 (8)*
H2A−0.001 (4)0.039 (2)0.8940 (17)0.074 (5)*
H8A−0.392 (5)0.072 (3)0.670 (2)0.127 (9)*
H8B−0.298 (5)0.034 (3)0.767 (3)0.133 (10)*
H8C−0.259 (6)−0.042 (4)0.637 (3)0.139 (11)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O30.0548 (6)0.0760 (7)0.0715 (7)−0.0132 (5)−0.0027 (5)0.0428 (6)
O10.0639 (7)0.0847 (8)0.0621 (6)−0.0099 (5)−0.0004 (5)0.0522 (6)
O20.0530 (6)0.0615 (6)0.0509 (5)−0.0086 (4)−0.0006 (4)0.0349 (5)
N10.0485 (6)0.0524 (6)0.0464 (6)0.0009 (4)0.0051 (5)0.0302 (5)
N20.0497 (7)0.0614 (7)0.0534 (6)−0.0050 (5)0.0018 (5)0.0365 (5)
C10.0476 (7)0.0474 (7)0.0444 (7)0.0075 (5)0.0079 (5)0.0239 (5)
C90.0533 (7)0.0528 (7)0.0499 (7)0.0019 (6)0.0069 (6)0.0306 (6)
C70.0426 (6)0.0461 (7)0.0435 (6)0.0042 (5)0.0072 (5)0.0209 (5)
C30.0708 (10)0.0677 (10)0.0746 (10)−0.0033 (7)0.0139 (8)0.0458 (8)
C20.0524 (8)0.0489 (7)0.0534 (7)0.0032 (5)0.0080 (6)0.0257 (6)
C100.0605 (9)0.0695 (10)0.0554 (8)−0.0072 (7)−0.0040 (7)0.0326 (7)
C80.0498 (8)0.0802 (11)0.0650 (9)−0.0084 (7)0.0004 (7)0.0454 (9)
C50.0723 (11)0.0932 (13)0.0665 (9)0.0105 (9)0.0020 (8)0.0531 (9)
C60.0535 (8)0.0794 (10)0.0601 (8)0.0011 (7)0.0020 (7)0.0417 (8)
C40.0878 (12)0.0808 (11)0.0724 (10)0.0118 (9)0.0155 (9)0.0552 (9)
C110.0631 (9)0.0640 (10)0.0740 (10)−0.0072 (7)0.0042 (8)0.0274 (8)

Geometric parameters (Å, °)

O3—C21.3543 (19)C3—H3B0.9300
O3—H3A0.98 (2)C10—C111.489 (2)
O1—C91.2173 (16)C10—H10A0.9700
O2—C91.3237 (17)C10—H10B0.9700
O2—C101.4563 (18)C8—H8A0.95 (3)
N1—C71.2836 (18)C8—H8B0.85 (3)
N1—N21.3790 (15)C8—H8C0.84 (3)
N2—C91.3521 (19)C5—C61.374 (2)
N2—H2A0.92 (2)C5—C41.381 (3)
C1—C61.393 (2)C5—H5A0.9300
C1—C21.408 (2)C6—H6A0.9300
C1—C71.4737 (18)C4—H4A0.9300
C7—C81.4988 (19)C11—H11A0.9600
C3—C41.365 (2)C11—H11B0.9600
C3—C21.395 (2)C11—H11C0.9600
C2—O3—H3A104.2 (15)O2—C10—H10B110.3
C9—O2—C10116.29 (10)C11—C10—H10B110.3
C7—N1—N2119.65 (11)H10A—C10—H10B108.6
C9—N2—N1119.71 (11)C7—C8—H8A112.7 (16)
C9—N2—H2A116.8 (11)C7—C8—H8B114 (2)
N1—N2—H2A123.3 (11)H8A—C8—H8B101 (2)
C6—C1—C2116.97 (12)C7—C8—H8C107 (2)
C6—C1—C7120.60 (12)H8A—C8—H8C105 (3)
C2—C1—C7122.43 (12)H8B—C8—H8C117 (3)
O1—C9—O2124.75 (13)C6—C5—C4118.87 (16)
O1—C9—N2121.90 (13)C6—C5—H5A120.6
O2—C9—N2113.34 (11)C4—C5—H5A120.6
N1—C7—C1116.09 (11)C5—C6—C1123.05 (15)
N1—C7—C8123.84 (12)C5—C6—H6A118.5
C1—C7—C8120.06 (12)C1—C6—H6A118.5
C4—C3—C2121.27 (14)C3—C4—C5120.15 (14)
C4—C3—H3B119.4C3—C4—H4A119.9
C2—C3—H3B119.4C5—C4—H4A119.9
O3—C2—C3117.02 (13)C10—C11—H11A109.5
O3—C2—C1123.31 (12)C10—C11—H11B109.5
C3—C2—C1119.67 (13)H11A—C11—H11B109.5
O2—C10—C11107.04 (13)C10—C11—H11C109.5
O2—C10—H10A110.3H11A—C11—H11C109.5
C11—C10—H10A110.3H11B—C11—H11C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.92 (2)2.05 (2)2.9649 (19)170.4 (16)
O3—H3A···N10.98 (3)1.68 (3)2.5728 (19)149 (2)

Symmetry codes: (i) −x, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2935).

References

  • Bruker (1997). SMART and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.
  • Girgis, A. S. (2006). J. Chem. Res. pp. 81–85.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • 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