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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2439.
Published online 2010 August 28. doi:  10.1107/S1600536810033398
PMCID: PMC3008100

2-[(E)-(2,3-Dimethyl­phen­yl)imino­meth­yl]phenol

Abstract

In the title compound, C15H15NO, the almost planar 2,3-dimethyl­aniline unit and the salicyl­aldehyde group (r.m.s. deviations of 0.0156 and 0.0109 Å, respectively) are oriented at a dihedral angle of 43.69 (9)° with respect to each other. An S(6) ring motif is formed due to intra­molecular O—H(...)N hydrogen bonding. In the crystal, C—H(...)π inter­actions occur between the 2,3-dimethyl­aniline unit and the salicyl­aldehyde group, where the CH is from the o-methyl group.

Related literature

For background to Schiff bases synthesized from 2,3-dimethyl­aniline and for related structures, see: Tahir et al. (2010a [triangle],b [triangle]); Tariq et al. (2010 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2439-scheme1.jpg

Experimental

Crystal data

  • C15H15NO
  • M r = 225.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2439-efi1.jpg
  • a = 7.5641 (7) Å
  • b = 12.5889 (13) Å
  • c = 13.0643 (14) Å
  • V = 1244.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.32 × 0.12 × 0.10 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.980, T max = 0.985
  • 9729 measured reflections
  • 1316 independent reflections
  • 687 reflections with I > 2σ(I)
  • R int = 0.085

Refinement

  • R[F 2 > 2σ(F 2)] = 0.078
  • wR(F 2) = 0.157
  • S = 1.11
  • 1316 reflections
  • 157 parameters
  • H-atom parameters constrained
  • Δρmax = 0.11 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033398/bq2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033398/bq2232Isup2.hkl

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

We have reported crystal structures of Schiff bases synthesized from 2,3-dimethylaniline (Tahir et al., 2010a, 2010b), (Tariq et al., 2010) and in continuation of this work, we report herein the structure and synthesis of the title compound (I, Fig. 1). The title compound has been synthesized for the preparation of different organometallic compounds.

In (I), the 2,3-dimethylaniline moiety A (C1–C8/N1) and the group B (C9—C15/O1) of salicylaldehyde are planar with r.m.s. deviations of 0.0156 and 0.0109 Å, respectively. The dihedral angle between A/B is 43.69 (9)°. The title molecule essentially consists of monomers. In the title molecule an S(6) ring motif (Bernstein et al., 1995) is formed due to intramolecular H-bonding of O—H···N type (Table 1, Fig. 1). There exist C—H···π interaction (Table 1) which plays important role in stabilizing the molecules.

Experimental

Equimolar quantities of 2,3-dimethylaniline and salicylaldehyde were refluxed in methanol for 45 min. The resulting solution was kept at room temperature which afforded colorless needles of (I) after 72 h.

Refinement

The H-atoms were positioned geometrically (O–H = 0.82, C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for all other H-atoms. In the absence of significant anomalous scattering factor, Friedal pairs were merged.

Figures

Fig. 1.
View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. The dotted line represents the intramolecular H-bonding.

Crystal data

C15H15NOF(000) = 480
Mr = 225.28Dx = 1.203 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 687 reflections
a = 7.5641 (7) Åθ = 2.3–25.2°
b = 12.5889 (13) ŵ = 0.08 mm1
c = 13.0643 (14) ÅT = 296 K
V = 1244.0 (2) Å3Needle, colorless
Z = 40.32 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer1316 independent reflections
Radiation source: fine-focus sealed tube687 reflections with I > 2σ(I)
graphiteRint = 0.085
Detector resolution: 8.1 pixels mm-1θmax = 25.2°, θmin = 2.3°
ω scansh = −9→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −15→15
Tmin = 0.980, Tmax = 0.985l = −15→15
9729 measured reflections

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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0624P)2] where P = (Fo2 + 2Fc2)/3
1316 reflections(Δ/σ)max < 0.001
157 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = −0.13 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
O1−0.1515 (5)0.5069 (3)0.2310 (3)0.0897 (19)
N1−0.0156 (5)0.3687 (4)0.1080 (3)0.0627 (17)
C10.0128 (6)0.3279 (4)0.0080 (4)0.056 (2)
C20.0758 (6)0.3945 (5)−0.0690 (5)0.059 (2)
C30.0952 (6)0.3556 (5)−0.1668 (4)0.065 (2)
C40.0551 (7)0.2503 (6)−0.1881 (5)0.077 (3)
C5−0.0066 (7)0.1849 (5)−0.1113 (5)0.083 (3)
C6−0.0298 (7)0.2231 (5)−0.0142 (5)0.072 (2)
C70.1219 (8)0.5080 (4)−0.0424 (5)0.088 (3)
C80.1642 (9)0.4236 (5)−0.2532 (4)0.106 (3)
C90.0214 (6)0.3121 (4)0.1866 (4)0.064 (2)
C10−0.0210 (7)0.3453 (4)0.2888 (4)0.061 (2)
C110.0197 (8)0.2804 (5)0.3715 (4)0.081 (2)
C12−0.0244 (10)0.3084 (6)0.4696 (5)0.095 (3)
C13−0.1103 (10)0.4022 (7)0.4868 (6)0.097 (3)
C14−0.1526 (7)0.4687 (5)0.4063 (6)0.088 (3)
C15−0.1088 (7)0.4403 (5)0.3083 (5)0.068 (3)
H1−0.117670.481680.176550.1075*
H40.069810.22390−0.254060.0926*
H5−0.032540.11425−0.125640.0997*
H6−0.074060.178950.036780.0859*
H7A0.248020.51622−0.041570.1311*
H7B0.074920.525070.023870.1311*
H7C0.071870.55492−0.092620.1311*
H8A0.088680.48428−0.261790.1586*
H8B0.165810.38290−0.315280.1586*
H8C0.281870.44699−0.237370.1586*
H90.077670.247160.177150.0767*
H110.078170.216540.360110.0969*
H120.003980.263970.523980.1147*
H13−0.140670.421360.553280.1166*
H14−0.210520.532610.418620.1054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.084 (3)0.075 (3)0.110 (4)0.023 (3)0.003 (3)−0.009 (3)
N10.049 (3)0.061 (3)0.078 (3)−0.008 (2)0.003 (3)−0.001 (3)
C10.038 (3)0.050 (4)0.081 (4)−0.001 (3)−0.005 (3)−0.001 (3)
C20.045 (3)0.057 (4)0.075 (4)−0.002 (3)−0.009 (3)0.010 (4)
C30.052 (3)0.071 (5)0.073 (4)0.001 (3)−0.015 (3)0.018 (4)
C40.071 (4)0.083 (5)0.077 (4)0.005 (3)−0.009 (3)−0.015 (4)
C50.078 (4)0.071 (5)0.101 (5)−0.011 (4)0.004 (4)−0.010 (4)
C60.071 (4)0.063 (4)0.081 (4)−0.012 (3)0.009 (3)0.005 (3)
C70.084 (4)0.057 (4)0.122 (5)−0.011 (4)−0.007 (4)0.015 (4)
C80.118 (6)0.113 (6)0.086 (5)−0.006 (5)−0.005 (4)0.019 (4)
C90.049 (3)0.056 (4)0.087 (4)0.001 (3)0.005 (3)−0.003 (4)
C100.055 (3)0.057 (4)0.071 (4)−0.003 (3)0.004 (3)−0.005 (3)
C110.090 (4)0.066 (4)0.086 (4)−0.004 (4)−0.002 (4)−0.007 (4)
C120.114 (6)0.089 (6)0.083 (5)−0.024 (5)0.003 (4)−0.003 (4)
C130.084 (5)0.112 (7)0.096 (5)−0.030 (5)0.019 (4)−0.031 (5)
C140.067 (4)0.078 (5)0.118 (6)−0.001 (3)0.003 (4)−0.018 (5)
C150.054 (3)0.065 (5)0.085 (5)−0.003 (3)0.005 (3)−0.006 (4)

Geometric parameters (Å, °)

O1—C151.352 (7)C13—C141.382 (11)
O1—H10.8200C14—C151.370 (10)
N1—C11.420 (7)C4—H40.9300
N1—C91.281 (7)C5—H50.9300
C1—C61.389 (8)C6—H60.9300
C1—C21.394 (8)C7—H7A0.9600
C2—C71.511 (8)C7—H7B0.9600
C2—C31.376 (8)C7—H7C0.9600
C3—C41.388 (10)C8—H8A0.9600
C3—C81.510 (8)C8—H8B0.9600
C4—C51.379 (9)C8—H8C0.9600
C5—C61.368 (9)C9—H90.9300
C9—C101.435 (7)C11—H110.9300
C10—C151.392 (8)C12—H120.9300
C10—C111.389 (8)C13—H130.9300
C11—C121.370 (9)C14—H140.9300
C12—C131.366 (11)
O1···N12.582 (6)H1···H7B2.5300
O1···H8Ci2.8900H4···H8B2.2700
N1···O12.582 (6)H5···C8v3.0400
N1···H11.8500H5···H8Av2.2400
N1···H7B2.3600H6···C92.6800
C1···C6ii3.520 (7)H6···H92.3300
C2···C6ii3.503 (8)H6···C2iii2.8400
C6···C2iii3.503 (8)H6···C3iii3.0600
C6···C1iii3.520 (7)H7A···C83.0700
C1···H13.0900H7A···C12vii3.0400
C2···H6ii2.8400H7A···C13vii2.9500
C2···H14iv2.9200H7B···N12.3600
C3···H6ii3.0600H7B···H12.5300
C5···H8Av3.0800H7C···C82.7600
C6···H92.6500H7C···H8A2.3900
C7···H8A2.8900H8A···C72.8900
C7···H8C2.9200H8A···H7C2.3900
C8···H7A3.0700H8A···C5vi3.0800
C8···H7C2.7600H8A···H5vi2.2400
C8···H5vi3.0400H8B···H42.2700
C9···H12.3800H8C···C72.9200
C9···H62.6800H8C···O1vii2.8900
C12···H7Ai3.0400H8C···C15vii2.9100
C13···H7Ai2.9500H9···C62.6500
C15···H8Ci2.9100H9···H62.3300
H1···N11.8500H9···H112.4200
H1···C13.0900H11···H92.4200
H1···C92.3800H14···C2viii2.9200
C15—O1—H1109.00C4—C5—H5120.00
C1—N1—C9120.2 (5)C6—C5—H5120.00
N1—C1—C2119.9 (5)C1—C6—H6120.00
C2—C1—C6120.0 (5)C5—C6—H6120.00
N1—C1—C6120.0 (5)C2—C7—H7A110.00
C1—C2—C3119.5 (6)C2—C7—H7B109.00
C1—C2—C7118.8 (5)C2—C7—H7C109.00
C3—C2—C7121.7 (6)H7A—C7—H7B109.00
C2—C3—C4120.2 (5)H7A—C7—H7C109.00
C2—C3—C8122.0 (5)H7B—C7—H7C109.00
C4—C3—C8117.9 (5)C3—C8—H8A109.00
C3—C4—C5119.9 (6)C3—C8—H8B109.00
C4—C5—C6120.5 (6)C3—C8—H8C109.00
C1—C6—C5119.9 (6)H8A—C8—H8B109.00
N1—C9—C10122.3 (5)H8A—C8—H8C109.00
C9—C10—C15121.8 (5)H8B—C8—H8C110.00
C11—C10—C15118.0 (5)N1—C9—H9119.00
C9—C10—C11120.2 (5)C10—C9—H9119.00
C10—C11—C12121.5 (6)C10—C11—H11119.00
C11—C12—C13119.5 (7)C12—C11—H11119.00
C12—C13—C14120.6 (7)C11—C12—H12120.00
C13—C14—C15119.8 (6)C13—C12—H12120.00
O1—C15—C14118.6 (5)C12—C13—H13120.00
C10—C15—C14120.7 (6)C14—C13—H13120.00
O1—C15—C10120.7 (5)C13—C14—H14120.00
C3—C4—H4120.00C15—C14—H14120.00
C5—C4—H4120.00
C9—N1—C1—C2−141.7 (5)C3—C4—C5—C60.4 (8)
C9—N1—C1—C641.3 (7)C4—C5—C6—C1−1.5 (8)
C1—N1—C9—C10−173.7 (4)N1—C9—C10—C11179.1 (5)
N1—C1—C2—C73.3 (7)N1—C9—C10—C151.5 (8)
C6—C1—C2—C30.0 (7)C9—C10—C11—C12−177.8 (6)
C6—C1—C2—C7−179.7 (5)C15—C10—C11—C12−0.1 (9)
N1—C1—C6—C5178.3 (5)C9—C10—C15—O1−2.5 (8)
C2—C1—C6—C51.2 (8)C9—C10—C15—C14178.0 (5)
N1—C1—C2—C3−177.0 (4)C11—C10—C15—O1179.8 (5)
C1—C2—C3—C4−1.1 (7)C11—C10—C15—C140.3 (8)
C7—C2—C3—C4178.7 (5)C10—C11—C12—C130.0 (10)
C7—C2—C3—C80.2 (8)C11—C12—C13—C14−0.1 (11)
C1—C2—C3—C8−179.5 (5)C12—C13—C14—C150.3 (10)
C2—C3—C4—C50.9 (8)C13—C14—C15—O1−179.9 (6)
C8—C3—C4—C5179.3 (5)C13—C14—C15—C10−0.4 (9)

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x+1/2, −y+1/2, −z; (iii) x−1/2, −y+1/2, −z; (iv) −x−1/2, −y+1, z−1/2; (v) −x, y−1/2, −z−1/2; (vi) −x, y+1/2, −z−1/2; (vii) −x+1/2, −y+1, z−1/2; (viii) −x−1/2, −y+1, z+1/2.

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.852.582 (6)148
C7—H7A···Cg1vii0.962.923.782 (6)150

Symmetry codes: (vii) −x+1/2, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2232).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010a). Acta Cryst. E66, o1562. [PMC free article] [PubMed]
  • Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010b). Acta Cryst. E66, o1817. [PMC free article] [PubMed]
  • Tariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561. [PMC free article] [PubMed]

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