organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(E)-2-(2,4-Di­hydroxy­benzyl­­idene­amino)benzo­nitrile

aBiology and Chemistry Department, Nanchang University College of Science and Technology, Nanchang 330029, People's Republic of China
*Correspondence e-mail: liuting_ncu@yahoo.cn

(Received 22 May 2009; accepted 27 May 2009; online 6 June 2009)

The mol­ecule of the title compound, C14H10N2O2, adopts the phenol–imine tautomeric form. The dihedral angle between the planes of the two benzene rings is 13.84 (13)°. A strong intra­molecular O—H⋯N hydrogen-bonding inter­action stabilizes the mol­ecular conformation. In the crystal structure, centrosymmetrically related mol­ecules are linked into dimers by inter­molecular C—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Cheng et al. (2006[Cheng, K., Zhu, H.-L., Li, Z.-B. & Yan, Z. (2006). Acta Cryst. E62, o2417-o2418.]); Xia et al. (2008[Xia, R., Xu, H.-J. & Gong, X.-X. (2008). Acta Cryst. E64, o1047.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10N2O2

  • Mr = 238.24

  • Monoclinic, P 21 /c

  • a = 13.322 (3) Å

  • b = 5.7505 (12) Å

  • c = 16.132 (3) Å

  • β = 108.97 (3)°

  • V = 1168.7 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.973, Tmax = 0.979

  • 11536 measured reflections

  • 2683 independent reflections

  • 1394 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.153

  • S = 1.01

  • 2683 reflections

  • 167 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯N2 0.95 (3) 1.70 (3) 2.581 (2) 152 (3)
O2—H2A⋯N1i 0.82 2.03 2.835 (3) 166
C11—H11A⋯O1i 0.93 2.56 3.386 (3) 148
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Schiff base compounds have attracted great attention and have been extensively investigated due to their important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures. Herein, the synthesis and crystal structure of the title compound is reported.

The molecular structure of the title compound is shown in Fig. 1. The Schiff-base molecule adopts a non-planar conformation, with the dihedral angle between the two aromatic rings of 13.84 (13)°, and displays a trans configuration with respect to the C8=N2 double bond. Bond lengths (Allen et al., 1987) and angles are normal and in good agreement with those reported for 5-chloro-2-(2-hydroxybenzylideneamino)benzonitrile (Cheng et al., 2006) and 2-(2-hydroxybenzylideneamino)benzonitrile (Xia et al., 2008). There is an strong intramolecular O—H···N hydrogen bond stabilizing the molecular conformation (Table 1). In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked into dimers by intermolecular C—H···O and O—H···N hydrogen bonds (Table 1).

Related literature top

For the crystal structure of related compounds, see: Cheng et al. (2006); Xia et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by refluxing a mixture of 2,4-dihydroxybenzaldehyde (0.552 g, 4 mmol) and 2-aminobenzonitrile (0.472 g, 4 mmol) in ethanol (20 ml). The reaction mixture was refluxed for 5 h under stirring, then cooled to room temperatureand and the resulting yellow precipitate was filtered off. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement top

The H bound to O1 was located in a difference Fourier map and refined freely. All other H atoms were located geometrically and treated as riding atoms, with O—H= 0.82 Å, C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound, showing the structure along the b axis. Hydrogen bonds are shown as dashed lines.
(E)-2-(2,4-Dihydroxybenzylideneamino)benzonitrile top
Crystal data top
C14H10N2O2F(000) = 496
Mr = 238.24Dx = 1.354 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8059 reflections
a = 13.322 (3) Åθ = 3.1–27.8°
b = 5.7505 (12) ŵ = 0.09 mm1
c = 16.132 (3) ÅT = 293 K
β = 108.97 (3)°Prism, yellow
V = 1168.7 (5) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer
2683 independent reflections
Radiation source: fine-focus sealed tube1394 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1717
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 77
Tmin = 0.973, Tmax = 0.979l = 2020
11536 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0648P)2]
where P = (Fo2 + 2Fc2)/3
2683 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C14H10N2O2V = 1168.7 (5) Å3
Mr = 238.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.322 (3) ŵ = 0.09 mm1
b = 5.7505 (12) ÅT = 293 K
c = 16.132 (3) Å0.20 × 0.20 × 0.20 mm
β = 108.97 (3)°
Data collection top
Rigaku SCXmini
diffractometer
2683 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1394 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.979Rint = 0.073
11536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.15 e Å3
2683 reflectionsΔρmin = 0.16 e Å3
167 parameters
Special details top

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) top
xyzUiso*/Ueq
O20.79346 (11)0.8933 (3)0.08149 (11)0.0566 (5)
H2A0.79110.76630.05780.085*
N20.33856 (14)0.9483 (3)0.12987 (11)0.0458 (5)
O10.45029 (14)0.6553 (3)0.07575 (12)0.0620 (5)
C80.41862 (18)1.0886 (4)0.14982 (14)0.0467 (6)
H8A0.41271.23270.17400.056*
C90.51588 (16)1.0290 (4)0.13590 (13)0.0413 (5)
C120.70129 (17)0.9304 (4)0.09842 (14)0.0430 (6)
C50.1263 (2)1.2217 (5)0.20046 (18)0.0709 (8)
H5A0.11641.34350.23490.085*
C30.05604 (19)0.8978 (5)0.10712 (18)0.0643 (7)
H3A0.00040.80090.07840.077*
C10.24136 (18)1.0047 (4)0.14176 (14)0.0466 (6)
C100.52810 (17)0.8164 (4)0.09675 (14)0.0434 (6)
C140.60082 (18)1.1854 (4)0.15679 (15)0.0506 (6)
H14A0.59471.32580.18340.061*
C110.61972 (16)0.7695 (4)0.07767 (14)0.0447 (6)
H11A0.62660.63000.05090.054*
C130.69260 (18)1.1384 (4)0.13929 (15)0.0514 (6)
H13A0.74841.24430.15450.062*
C20.15547 (18)0.8609 (4)0.09949 (15)0.0500 (6)
C70.17047 (19)0.6737 (5)0.04576 (18)0.0575 (7)
N10.18114 (18)0.5237 (4)0.00325 (17)0.0777 (8)
C60.22459 (19)1.1855 (5)0.19264 (16)0.0598 (7)
H6A0.28061.28320.22180.072*
C40.0418 (2)1.0796 (5)0.15775 (18)0.0707 (8)
H4A0.02471.10650.16320.085*
H1A0.392 (2)0.729 (5)0.0876 (17)0.090 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0453 (10)0.0602 (11)0.0695 (12)0.0039 (8)0.0261 (8)0.0088 (8)
N20.0384 (10)0.0558 (12)0.0429 (11)0.0041 (10)0.0130 (8)0.0002 (9)
O10.0445 (10)0.0547 (11)0.0895 (14)0.0107 (9)0.0256 (9)0.0253 (9)
C80.0512 (14)0.0476 (14)0.0432 (14)0.0018 (12)0.0179 (11)0.0039 (10)
C90.0415 (13)0.0418 (13)0.0405 (13)0.0001 (11)0.0133 (10)0.0021 (10)
C120.0384 (12)0.0508 (14)0.0401 (13)0.0001 (11)0.0131 (10)0.0016 (10)
C50.0568 (16)0.096 (2)0.0643 (18)0.0081 (17)0.0256 (14)0.0210 (16)
C30.0468 (15)0.0802 (19)0.0698 (18)0.0065 (14)0.0241 (13)0.0108 (15)
C10.0435 (13)0.0595 (15)0.0386 (13)0.0060 (12)0.0155 (10)0.0039 (11)
C100.0397 (13)0.0443 (13)0.0429 (13)0.0042 (11)0.0092 (10)0.0004 (10)
C140.0545 (15)0.0418 (14)0.0574 (15)0.0033 (12)0.0209 (12)0.0087 (11)
C110.0422 (13)0.0449 (13)0.0468 (13)0.0001 (11)0.0142 (10)0.0082 (10)
C130.0472 (14)0.0504 (15)0.0598 (16)0.0117 (12)0.0218 (12)0.0073 (12)
C20.0448 (14)0.0572 (15)0.0507 (15)0.0011 (12)0.0192 (11)0.0018 (12)
C70.0501 (15)0.0586 (17)0.0681 (18)0.0079 (13)0.0252 (13)0.0053 (14)
N10.0735 (17)0.0691 (16)0.0994 (19)0.0109 (14)0.0406 (14)0.0236 (15)
C60.0499 (15)0.0781 (19)0.0521 (15)0.0044 (14)0.0176 (12)0.0176 (14)
C40.0499 (16)0.099 (2)0.0692 (19)0.0031 (16)0.0278 (14)0.0109 (16)
Geometric parameters (Å, º) top
O2—C121.359 (2)C3—C41.377 (3)
O2—H2A0.8200C3—C21.386 (3)
N2—C81.292 (3)C3—H3A0.9300
N2—C11.407 (3)C1—C61.387 (3)
O1—C101.349 (3)C1—C21.397 (3)
O1—H1A0.95 (3)C10—C111.379 (3)
C8—C91.427 (3)C14—C131.368 (3)
C8—H8A0.9300C14—H14A0.9300
C9—C141.398 (3)C11—H11A0.9300
C9—C101.409 (3)C13—H13A0.9300
C12—C111.383 (3)C2—C71.436 (3)
C12—C131.389 (3)C7—N11.139 (3)
C5—C61.372 (3)C6—H6A0.9300
C5—C41.380 (4)C4—H4A0.9300
C5—H5A0.9300
C12—O2—H2A109.5O1—C10—C9121.1 (2)
C8—N2—C1123.0 (2)C11—C10—C9120.6 (2)
C10—O1—H1A104.5 (17)C13—C14—C9122.0 (2)
N2—C8—C9122.0 (2)C13—C14—H14A119.0
N2—C8—H8A119.0C9—C14—H14A119.0
C9—C8—H8A119.0C12—C11—C10119.9 (2)
C14—C9—C10117.6 (2)C12—C11—H11A120.1
C14—C9—C8120.9 (2)C10—C11—H11A120.1
C10—C9—C8121.5 (2)C14—C13—C12119.1 (2)
O2—C12—C11122.5 (2)C14—C13—H13A120.5
O2—C12—C13116.8 (2)C12—C13—H13A120.5
C11—C12—C13120.7 (2)C3—C2—C1121.4 (2)
C6—C5—C4120.8 (3)C3—C2—C7119.5 (2)
C6—C5—H5A119.6C1—C2—C7119.1 (2)
C4—C5—H5A119.6N1—C7—C2179.0 (3)
C4—C3—C2119.3 (2)C5—C6—C1120.7 (2)
C4—C3—H3A120.4C5—C6—H6A119.7
C2—C3—H3A120.4C1—C6—H6A119.7
C6—C1—C2117.9 (2)C3—C4—C5119.9 (2)
C6—C1—N2125.9 (2)C3—C4—H4A120.1
C2—C1—N2116.2 (2)C5—C4—H4A120.1
O1—C10—C11118.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.95 (3)1.70 (3)2.581 (2)152 (3)
O2—H2A···N1i0.822.032.835 (3)166
C11—H11A···O1i0.932.563.386 (3)148
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H10N2O2
Mr238.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.322 (3), 5.7505 (12), 16.132 (3)
β (°) 108.97 (3)
V3)1168.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.973, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
11536, 2683, 1394
Rint0.073
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.153, 1.01
No. of reflections2683
No. of parameters167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.95 (3)1.70 (3)2.581 (2)152 (3)
O2—H2A···N1i0.822.032.835 (3)166.3
C11—H11A···O1i0.932.563.386 (3)148
Symmetry code: (i) x+1, y+1, z.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationCheng, K., Zhu, H.-L., Li, Z.-B. & Yan, Z. (2006). Acta Cryst. E62, o2417–o2418.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXia, R., Xu, H.-J. & Gong, X.-X. (2008). Acta Cryst. E64, o1047.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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