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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-3-(2-Hy­dr­oxy-5-methyl­phenyl­imino)­indolin-2-one

aKey Laboratory of Marine Chemistry, Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
*Correspondence e-mail: bicaifeng301@163.com

(Received 24 June 2011; accepted 19 August 2011; online 27 August 2011)

In the title compound, C15H12N2O2, the dihedral angle between the two benzene rings is 83.55 (11)° In the crystal, the molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background on Schiff base ligands, see: Guo et al. (2011[Guo, A., Zhang, S., Liu, X. & Jiao, J. (2011). Acta Cryst. E67, o285.]); Drozdzak et al. (2005[Drozdzak, R., Allaert, B., Ledoux, N., Dragutan, I., Dragutan, V. & Verpoort, F. (2005). Coord. Chem. Rev. 249, 3055-3074.]); Weber et al. (2007[Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159-1162.]); Liu et al. (2010[Liu, S.-B., Bi, C.-F., Wang, Q., Zuo, J. & Fan, Y.-H. (2010). Acta Cryst. E66, o1361.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.])

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O2

  • Mr = 252.27

  • Monoclinic, P 21 /c

  • a = 12.6211 (11) Å

  • b = 8.7100 (7) Å

  • c = 11.2835 (10) Å

  • β = 90.780 (1)°

  • V = 1240.28 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.50 × 0.47 × 0.17 mm

Data collection
  • CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.956, Tmax = 0.985

  • 5982 measured reflections

  • 2182 independent reflections

  • 1449 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.114

  • S = 1.02

  • 2182 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 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
O2—H2⋯O1i 0.82 1.86 2.6729 (19) 169
N1—H1⋯O2ii 0.86 2.06 2.842 (2) 151
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); 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: SHELXTL.

Supporting information


Comment top

Being one of the most prevalent sustems in coordination chemistry, Schiff base ligands have received much attention in recent years (Guo et al., 2011), primarily due to their importance in metal complexes with catalytic activities (Drozdzak et al., 2005), special magnetism (Weber et al., 2007) and biological properties, for example, anticancer activities (Liu et al., 2010). In the present paper, the synthesis and structure of a new Schiff base ligand is reported.

The crystal structure of the new ligand is given in Fig.1. The molecular structure of the compound is not coplanar, the dihedral angle between the two benzene rings is 83.55 °, it is almost perpendicular. The bond lengths and angles (Table 1) are within normal values (Allen et al.,1987). In the crystal structure, the adjacent molecules are linked through 0—H···0 and N—H···O hydrogen bonding (Table 2), to generate one-dimensional chain in direction (Fig.2).

Related literature top

For general background on Schiff base ligands, see: Guo et al. (2011); Drozdzak et al. (2005); Weber et al. (2007); Liu et al. (2010). For standard bond lengths, see: Allen et al. (1987)

Experimental top

2,3-indolinedione (5 mmol, 0.736 g) was dissolved in anhydrous ethanol (20 ml), then an anhydrous ethanol solution (10 ml) of 2-amino-4-methylphenol (5 mmol, 0.612 g) was slowly added. The mixture was refluxed for 4 h at 333k,and then cooled down to room temperature. A dark brown solid separated out. The solid was filtered off, washed several times with anhydrous ethanol and dried in vacuum drier. The dark brown single-crystal of the title ligand suitable for X-ray diffraction was trained in anhydrous ethanol at room temperature.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 Å (methyl), 0.93 Å (methenyl), 0.93 Å (aromatic), and Uiso(H) =1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. A view of the crystal structure showing chain to the c linked via O—H···O and N—H···O contacts.
(E)-3-(2-Hydroxy-5-methylphenylimino)indolin-2-one top
Crystal data top
C15H12N2O2F(000) = 528
Mr = 252.27Dx = 1.351 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 1807 reflections
a = 12.6211 (11) Åθ = 2.8–25.8°
b = 8.7100 (7) ŵ = 0.09 mm1
c = 11.2835 (10) ÅT = 298 K
β = 90.780 (1)°Block, dark-brown
V = 1240.28 (18) Å30.50 × 0.47 × 0.17 mm
Z = 4
Data collection top
CCD area-detector
diffractometer
2182 independent reflections
Radiation source: fine-focus sealed tube1449 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1414
Tmin = 0.956, Tmax = 0.985k = 1010
5982 measured reflectionsl = 1013
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.3363P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2182 reflectionsΔρmax = 0.16 e Å3
173 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (2)
Crystal data top
C15H12N2O2V = 1240.28 (18) Å3
Mr = 252.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.6211 (11) ŵ = 0.09 mm1
b = 8.7100 (7) ÅT = 298 K
c = 11.2835 (10) Å0.50 × 0.47 × 0.17 mm
β = 90.780 (1)°
Data collection top
CCD area-detector
diffractometer
2182 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1449 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.985Rint = 0.038
5982 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
2182 reflectionsΔρmin = 0.16 e Å3
173 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
N10.53216 (12)0.37862 (19)0.37637 (13)0.0391 (4)
H10.48650.37850.31910.047*
N20.62133 (12)0.28888 (19)0.66041 (14)0.0404 (4)
O10.45391 (11)0.19850 (16)0.49452 (12)0.0474 (4)
O20.58728 (11)0.51425 (16)0.82237 (12)0.0490 (4)
H20.58300.57500.87760.073*
C10.52386 (15)0.2918 (2)0.47439 (16)0.0358 (5)
C20.61738 (14)0.3381 (2)0.55449 (16)0.0355 (5)
C30.67930 (15)0.4476 (2)0.48520 (17)0.0384 (5)
C40.62382 (14)0.4693 (2)0.37841 (17)0.0369 (5)
C50.65726 (16)0.5680 (2)0.29187 (18)0.0465 (5)
H50.61880.58160.22180.056*
C60.75054 (18)0.6460 (3)0.3136 (2)0.0564 (6)
H60.77560.71370.25670.068*
C70.80770 (18)0.6262 (3)0.4179 (2)0.0611 (7)
H70.87040.68050.42990.073*
C80.77297 (16)0.5266 (3)0.5045 (2)0.0519 (6)
H80.81180.51310.57440.062*
C90.68333 (15)0.4423 (2)0.82729 (17)0.0400 (5)
C100.70454 (15)0.3352 (2)0.73941 (16)0.0398 (5)
C110.80213 (16)0.2627 (3)0.73843 (19)0.0496 (6)
H110.81610.19200.67890.059*
C120.87940 (17)0.2925 (3)0.8235 (2)0.0566 (6)
C130.85588 (18)0.3980 (3)0.9110 (2)0.0596 (7)
H130.90640.41950.96950.072*
C140.75915 (17)0.4720 (3)0.91347 (19)0.0516 (6)
H140.74510.54210.97340.062*
C150.98450 (19)0.2096 (4)0.8213 (3)0.0907 (10)
H15A1.03910.27570.85220.136*
H15B1.00060.18170.74120.136*
H15C0.98060.11860.86910.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0391 (9)0.0482 (10)0.0300 (9)0.0008 (8)0.0053 (7)0.0017 (8)
N20.0432 (9)0.0452 (10)0.0326 (9)0.0010 (8)0.0054 (7)0.0002 (8)
O10.0487 (8)0.0530 (9)0.0403 (8)0.0093 (7)0.0018 (6)0.0006 (7)
O20.0542 (9)0.0530 (9)0.0395 (8)0.0082 (7)0.0098 (7)0.0066 (7)
C10.0389 (11)0.0384 (12)0.0300 (11)0.0044 (9)0.0008 (8)0.0030 (9)
C20.0397 (10)0.0358 (11)0.0311 (11)0.0069 (9)0.0014 (8)0.0030 (9)
C30.0399 (11)0.0400 (12)0.0352 (11)0.0019 (9)0.0009 (9)0.0006 (9)
C40.0391 (11)0.0383 (12)0.0335 (11)0.0057 (9)0.0028 (8)0.0010 (9)
C50.0520 (13)0.0494 (13)0.0380 (12)0.0034 (11)0.0011 (10)0.0066 (10)
C60.0611 (14)0.0521 (15)0.0562 (15)0.0070 (12)0.0071 (12)0.0141 (12)
C70.0560 (14)0.0610 (16)0.0660 (16)0.0177 (12)0.0049 (12)0.0104 (13)
C80.0507 (13)0.0544 (15)0.0502 (13)0.0066 (11)0.0090 (10)0.0062 (11)
C90.0425 (12)0.0432 (12)0.0341 (11)0.0041 (9)0.0055 (9)0.0061 (10)
C100.0424 (11)0.0466 (13)0.0302 (11)0.0049 (10)0.0037 (8)0.0053 (9)
C110.0457 (12)0.0609 (15)0.0421 (13)0.0020 (11)0.0026 (10)0.0035 (11)
C120.0414 (12)0.0746 (17)0.0537 (14)0.0034 (12)0.0054 (10)0.0126 (13)
C130.0507 (14)0.0753 (18)0.0523 (15)0.0169 (13)0.0190 (11)0.0100 (14)
C140.0597 (14)0.0541 (14)0.0405 (13)0.0083 (12)0.0115 (10)0.0005 (11)
C150.0469 (14)0.133 (3)0.092 (2)0.0122 (17)0.0062 (14)0.013 (2)
Geometric parameters (Å, º) top
N1—C11.345 (2)C7—C81.383 (3)
N1—C41.401 (2)C7—H70.9300
N1—H10.8600C8—H80.9300
N2—C21.270 (2)C9—C141.380 (3)
N2—C101.427 (2)C9—C101.390 (3)
O1—C11.223 (2)C10—C111.384 (3)
O2—C91.365 (2)C11—C121.383 (3)
O2—H20.8200C11—H110.9300
C1—C21.531 (3)C12—C131.384 (3)
C2—C31.466 (3)C12—C151.511 (3)
C3—C81.383 (3)C13—C141.381 (3)
C3—C41.398 (3)C13—H130.9300
C4—C51.372 (3)C14—H140.9300
C5—C61.379 (3)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C6—C71.383 (3)C15—H15C0.9600
C6—H60.9300
C1—N1—C4112.15 (16)C3—C8—H8120.7
C1—N1—H1123.9C7—C8—H8120.7
C4—N1—H1123.9O2—C9—C14123.33 (19)
C2—N2—C10120.77 (17)O2—C9—C10117.30 (17)
C9—O2—H2109.5C14—C9—C10119.36 (19)
O1—C1—N1126.19 (18)C11—C10—C9119.46 (18)
O1—C1—C2128.17 (17)C11—C10—N2120.89 (19)
N1—C1—C2105.61 (16)C9—C10—N2119.23 (17)
N2—C2—C3135.01 (18)C12—C11—C10121.9 (2)
N2—C2—C1119.12 (17)C12—C11—H11119.1
C3—C2—C1105.61 (15)C10—C11—H11119.1
C8—C3—C4119.07 (19)C11—C12—C13117.6 (2)
C8—C3—C2134.48 (18)C11—C12—C15120.7 (2)
C4—C3—C2106.45 (16)C13—C12—C15121.7 (2)
C5—C4—C3122.87 (19)C14—C13—C12121.5 (2)
C5—C4—N1127.13 (18)C14—C13—H13119.2
C3—C4—N1109.99 (17)C12—C13—H13119.2
C4—C5—C6116.9 (2)C9—C14—C13120.2 (2)
C4—C5—H5121.5C9—C14—H14119.9
C6—C5—H5121.5C13—C14—H14119.9
C5—C6—C7121.6 (2)C12—C15—H15A109.5
C5—C6—H6119.2C12—C15—H15B109.5
C7—C6—H6119.2H15A—C15—H15B109.5
C6—C7—C8120.9 (2)C12—C15—H15C109.5
C6—C7—H7119.6H15A—C15—H15C109.5
C8—C7—H7119.6H15B—C15—H15C109.5
C3—C8—C7118.6 (2)
C4—N1—C1—O1177.50 (18)C4—C5—C6—C70.2 (3)
C4—N1—C1—C24.1 (2)C5—C6—C7—C80.0 (4)
C10—N2—C2—C34.0 (3)C4—C3—C8—C70.9 (3)
C10—N2—C2—C1177.06 (16)C2—C3—C8—C7178.5 (2)
O1—C1—C2—N27.8 (3)C6—C7—C8—C30.4 (4)
N1—C1—C2—N2170.58 (17)O2—C9—C10—C11177.98 (17)
O1—C1—C2—C3177.25 (18)C14—C9—C10—C111.3 (3)
N1—C1—C2—C34.36 (19)O2—C9—C10—N29.3 (3)
N2—C2—C3—C88.8 (4)C14—C9—C10—N2171.34 (18)
C1—C2—C3—C8177.5 (2)C2—N2—C10—C1182.8 (2)
N2—C2—C3—C4170.7 (2)C2—N2—C10—C9104.6 (2)
C1—C2—C3—C43.1 (2)C9—C10—C11—C120.7 (3)
C8—C3—C4—C51.1 (3)N2—C10—C11—C12171.90 (19)
C2—C3—C4—C5178.45 (18)C10—C11—C12—C130.2 (3)
C8—C3—C4—N1179.66 (17)C10—C11—C12—C15179.0 (2)
C2—C3—C4—N10.8 (2)C11—C12—C13—C140.4 (3)
C1—N1—C4—C5178.56 (19)C15—C12—C13—C14179.1 (2)
C1—N1—C4—C32.2 (2)O2—C9—C14—C13178.12 (19)
C3—C4—C5—C60.7 (3)C10—C9—C14—C131.2 (3)
N1—C4—C5—C6179.83 (19)C12—C13—C14—C90.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.862.6729 (19)169
N1—H1···O2ii0.862.062.842 (2)151
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC15H12N2O2
Mr252.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.6211 (11), 8.7100 (7), 11.2835 (10)
β (°) 90.780 (1)
V3)1240.28 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.47 × 0.17
Data collection
DiffractometerCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.956, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
5982, 2182, 1449
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.114, 1.02
No. of reflections2182
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.16

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
N2—C21.270 (2)C2—C31.466 (3)
N2—C101.427 (2)C9—C101.390 (3)
C1—C21.531 (3)C10—C111.384 (3)
C2—N2—C10120.77 (17)O2—C9—C10117.30 (17)
N2—C2—C3135.01 (18)C11—C10—N2120.89 (19)
N2—C2—C1119.12 (17)C9—C10—N2119.23 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.862.6729 (19)168.8
N1—H1···O2ii0.862.062.842 (2)150.7
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y+1, z+1.
 

Acknowledgements

The authors acknowledge the National Science Foundation of China for its financial support of this project (project No. 21071134).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Google Scholar
First citationDrozdzak, R., Allaert, B., Ledoux, N., Dragutan, I., Dragutan, V. & Verpoort, F. (2005). Coord. Chem. Rev. 249, 3055–3074.  Web of Science CrossRef CAS Google Scholar
First citationGuo, A., Zhang, S., Liu, X. & Jiao, J. (2011). Acta Cryst. E67, o285.  CrossRef IUCr Journals Google Scholar
First citationLiu, S.-B., Bi, C.-F., Wang, Q., Zuo, J. & Fan, Y.-H. (2010). Acta Cryst. E66, o1361.  CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationWeber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds