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

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2-[(E)-(5-Chloro-2-methyl­phen­yl)imino­meth­yl]-4-methyl­phenol

aDepartment of Chemistry, Lishui University, Lishui 323000, People's Republic of China
*Correspondence e-mail: fan200203@163.com

(Received 10 July 2013; accepted 14 July 2013; online 27 July 2013)

In the mol­ecule of the title Schiff base compound, C15H14ClNO, the two benzene rings are twisted with respect to each other, with a dihedral angle of 35.0 (3)°; an intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, weak C—H⋯π inter­actions between methyl groups and chloro­phenyl rings link the mol­ecules into supra­molecular chains running along the a axis.

Related literature

For background to phyenyl­amine compounds, see: Fan et al. (2012[Fan, C.-B., Wang, X.-M., Ding, P., Wang, J.-J., Liang, Z.-Q. & Tao, X.-T. (2012). Dyes Pigm. 95, 757-767.]). For applications of Schiff base derivatives, see: Siddiqui et al. (2006[Siddiqui, J. I., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206-211.]); Ebrahimipour et al. (2012[Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14ClNO

  • Mr = 259.72

  • Orthorhombic, P 21 21 21

  • a = 7.6629 (10) Å

  • b = 11.8442 (14) Å

  • c = 14.342 (2) Å

  • V = 1301.7 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 293 K

  • 0.45 × 0.42 × 0.35 mm

Data collection
  • Agilent Xcalibur Gemini ultra diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.88, Tmax = 0.91

  • 8663 measured reflections

  • 2382 independent reflections

  • 1769 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.100

  • S = 1.03

  • 2382 reflections

  • 169 parameters

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

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.17 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 991 Friedel pairs

  • Absolute structure parameter: −0.18 (9)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.84 (4) 1.84 (4) 2.629 (3) 154 (4)
C7—H7CCg1i 0.96 2.91 3.767 (3) 149
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Phyenylamine group has received attention in recent years for their unique physical and chemical properties (Fan et al., 2012). On the other hand, Schiff bases derived from salicyladehyde and methylaniline with varous substituents have exhibited potential application in pharmaceutical field for their properties of antitumor, antimicrobial and antiviral activities (Siddiqui et al., 2006). Moreover, Schiff bases ligands are potentially capable of forming stable complexes by coordination of metal ions with their nitrogen donors (Ebrahimipour et al., 2012). As an extension work on the structural characterization of Schiff base compounds, the title compound is reported.

The molecular structure of title compound shows an E configuration, with a C9—N1C8—C6 torsion angle of 0.26 (4)°. The bond distance of N1C8 at 1.284 (3)Å is a typical double bond. It is noteworthy that H1 atom bonded to O1 is involved in an O1—H1···N1 intramolecular hydrogen bond, which results in formation of a six-membered ring (Fig. 1). The dihedral angle between the two planes of the chlorophyenyl ring and methylphenol ring is 35.0 (3)°.

Related literature top

For background to phyenylamine compounds, see: Fan et al. (2012). For applications of Schiff base derivatives, see: Siddiqui et al. (2006); Ebrahimipour et al. (2012).

Experimental top

A mixture of 5-chloro-2-methylaniline (1.42g, 10.0 mmol), 3-methyl-2-hydroxybenzaldehyde (1.36g, 10.0 mmol) in 50.0 ml CH2Cl2 was fluxed under an Ar atmosphere for about 6 h to gain a yellow precipitate. The product was collected by filtration and washed with cold ethanol to give the Schiff base compound (2.25g in 86% yield). The yellow single crystals suitable for X-ray analysis were crystallized from CH2Cl2/absolute ethanol (3/2) systems by slow evaporation of solvents at room temperature over a week. Elemental analysis. Calc. for C15H14ClNO: C 69.36, H, 6.43%; Found C 69.92, H 6.80%.

Refinement top

Hydroxy H atom was located in a difference Fourier map and positional parameters were refined freely, Uiso(H) = 1.5Ueq(O). Other H atoms were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl) or 0.93 Å (aromatic), Uiso(H) = 1.2Ueq(C) for aromatic H atoms or Uiso(H) = 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the title compound. Ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radius. The dashed line indicates the intramolecular hydrogen bond.
[Figure 2] Fig. 2. Thermal ellipsoid plot of the title compound. Ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radius.
2-[(E)-(5-Chloro-2-methylphenyl)iminomethyl]-4-methylphenol top
Crystal data top
C15H14ClNOF(000) = 544
Mr = 259.72Dx = 1.325 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1894 reflections
a = 7.6629 (10) Åθ = 3.4–29.6°
b = 11.8442 (14) ŵ = 0.28 mm1
c = 14.342 (2) ÅT = 293 K
V = 1301.7 (3) Å3Block, yellow
Z = 40.45 × 0.42 × 0.35 mm
Data collection top
Agilent Xcalibur Gemini ultra
diffractometer with Atlas detector
2382 independent reflections
Radiation source: fine-focus sealed tube1769 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 10.3592 pixels mm-1θmax = 25.4°, θmin = 3.4°
ω scansh = 97
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 1414
Tmin = 0.88, Tmax = 0.91l = 1517
8663 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0463P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max = 0.002
S = 1.03Δρmax = 0.16 e Å3
2382 reflectionsΔρmin = 0.17 e Å3
169 parametersExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.024 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 991 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.18 (9)
Crystal data top
C15H14ClNOV = 1301.7 (3) Å3
Mr = 259.72Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.6629 (10) ŵ = 0.28 mm1
b = 11.8442 (14) ÅT = 293 K
c = 14.342 (2) Å0.45 × 0.42 × 0.35 mm
Data collection top
Agilent Xcalibur Gemini ultra
diffractometer with Atlas detector
2382 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
1769 reflections with I > 2σ(I)
Tmin = 0.88, Tmax = 0.91Rint = 0.048
8663 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100Δρmax = 0.16 e Å3
S = 1.03Δρmin = 0.17 e Å3
2382 reflectionsAbsolute structure: Flack (1983), with 991 Friedel pairs
169 parametersAbsolute structure parameter: 0.18 (9)
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl10.87007 (10)0.98698 (7)0.87968 (5)0.0705 (3)
O11.1714 (3)1.01909 (17)0.36679 (14)0.0651 (6)
N11.0171 (3)0.99976 (18)0.52972 (14)0.0456 (5)
C11.1228 (3)1.1295 (2)0.36948 (19)0.0449 (6)
C21.1680 (4)1.1989 (2)0.2958 (2)0.0510 (7)
H21.23271.17050.24620.061*
C31.1167 (4)1.3109 (2)0.29627 (19)0.0498 (7)
H31.14491.35610.24540.060*
C41.0248 (3)1.3579 (2)0.36974 (19)0.0451 (7)
C50.9829 (3)1.2883 (2)0.44320 (19)0.0421 (6)
H50.92151.31810.49340.050*
C61.0296 (3)1.1738 (2)0.44475 (18)0.0395 (6)
C70.9729 (4)1.4803 (2)0.3692 (2)0.0653 (8)
H7A0.88601.49320.41620.098*
H7B0.92611.49960.30920.098*
H7C1.07331.52630.38180.098*
C80.9758 (3)1.1045 (2)0.52278 (19)0.0458 (7)
H80.90871.13700.56970.055*
C90.9585 (3)0.9368 (2)0.6085 (2)0.0446 (7)
C100.9508 (3)0.9850 (2)0.69650 (18)0.0459 (6)
H100.98831.05890.70550.055*
C110.8874 (4)0.9232 (2)0.77061 (19)0.0493 (7)
C120.8366 (4)0.8127 (3)0.7589 (2)0.0596 (8)
H120.79430.77100.80890.071*
C130.8498 (4)0.7652 (2)0.6719 (2)0.0593 (8)
H130.81680.69010.66440.071*
C140.9102 (3)0.8243 (2)0.5945 (2)0.0503 (7)
C150.9174 (4)0.7697 (2)0.5002 (2)0.0680 (9)
H15A1.03510.77150.47730.102*
H15B0.84270.80990.45790.102*
H15C0.87910.69270.50500.102*
H11.136 (5)0.993 (3)0.418 (3)0.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0837 (5)0.0789 (6)0.0487 (5)0.0012 (4)0.0059 (4)0.0083 (4)
O10.0850 (14)0.0494 (12)0.0608 (14)0.0107 (11)0.0181 (11)0.0039 (11)
N10.0509 (12)0.0429 (12)0.0430 (13)0.0007 (12)0.0008 (10)0.0014 (11)
C10.0489 (14)0.0421 (14)0.0439 (17)0.0003 (12)0.0010 (14)0.0065 (13)
C20.0581 (17)0.0534 (17)0.0414 (16)0.0070 (14)0.0103 (14)0.0092 (14)
C30.0590 (16)0.0519 (16)0.0386 (16)0.0127 (16)0.0026 (14)0.0014 (13)
C40.0463 (14)0.0429 (14)0.0460 (18)0.0033 (12)0.0052 (13)0.0036 (13)
C50.0442 (14)0.0442 (14)0.0378 (16)0.0006 (12)0.0034 (12)0.0058 (12)
C60.0409 (13)0.0416 (14)0.0360 (16)0.0039 (12)0.0008 (12)0.0009 (12)
C70.0764 (19)0.0512 (16)0.068 (2)0.0039 (16)0.0027 (17)0.0091 (17)
C80.0445 (15)0.0480 (15)0.0447 (18)0.0003 (13)0.0003 (13)0.0012 (13)
C90.0411 (14)0.0421 (14)0.0505 (19)0.0006 (11)0.0003 (13)0.0066 (13)
C100.0464 (14)0.0417 (13)0.0497 (17)0.0017 (13)0.0003 (12)0.0056 (14)
C110.0475 (16)0.0528 (16)0.0475 (18)0.0044 (14)0.0002 (14)0.0111 (13)
C120.0596 (19)0.0546 (19)0.064 (2)0.0002 (15)0.0067 (15)0.0199 (16)
C130.0618 (19)0.0399 (15)0.076 (2)0.0021 (14)0.0013 (17)0.0095 (16)
C140.0469 (16)0.0437 (15)0.060 (2)0.0048 (13)0.0010 (14)0.0052 (14)
C150.075 (2)0.0530 (17)0.076 (2)0.0040 (16)0.0029 (17)0.0109 (17)
Geometric parameters (Å, º) top
Cl1—C111.742 (3)C7—H7B0.9600
O1—C11.361 (3)C7—H7C0.9600
O1—H10.84 (4)C8—H80.9300
N1—C81.284 (3)C9—C101.387 (4)
N1—C91.426 (3)C9—C141.397 (3)
C1—C21.383 (4)C10—C111.379 (3)
C1—C61.396 (3)C10—H100.9300
C2—C31.383 (4)C11—C121.376 (4)
C2—H20.9300C12—C131.372 (4)
C3—C41.384 (4)C12—H120.9300
C3—H30.9300C13—C141.392 (4)
C4—C51.376 (3)C13—H130.9300
C4—C71.503 (4)C14—C151.501 (4)
C5—C61.403 (3)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C6—C81.448 (3)C15—H15C0.9600
C7—H7A0.9600
C1—O1—H1104 (3)N1—C8—H8118.8
C8—N1—C9119.3 (2)C6—C8—H8118.8
O1—C1—C2118.8 (2)C10—C9—C14120.8 (2)
O1—C1—C6121.5 (2)C10—C9—N1121.2 (2)
C2—C1—C6119.7 (2)C14—C9—N1117.9 (2)
C1—C2—C3119.7 (3)C11—C10—C9119.8 (2)
C1—C2—H2120.2C11—C10—H10120.1
C3—C2—H2120.2C9—C10—H10120.1
C2—C3—C4122.3 (2)C12—C11—C10120.7 (3)
C2—C3—H3118.9C12—C11—Cl1120.1 (2)
C4—C3—H3118.9C10—C11—Cl1119.3 (2)
C5—C4—C3117.4 (2)C13—C12—C11118.7 (3)
C5—C4—C7121.3 (2)C13—C12—H12120.6
C3—C4—C7121.3 (2)C11—C12—H12120.6
C4—C5—C6122.1 (2)C12—C13—C14122.9 (3)
C4—C5—H5118.9C12—C13—H13118.6
C6—C5—H5118.9C14—C13—H13118.6
C1—C6—C5118.7 (2)C13—C14—C9117.0 (3)
C1—C6—C8122.1 (2)C13—C14—C15121.0 (2)
C5—C6—C8119.2 (2)C9—C14—C15122.0 (3)
C4—C7—H7A109.5C14—C15—H15A109.5
C4—C7—H7B109.5C14—C15—H15B109.5
H7A—C7—H7B109.5H15A—C15—H15B109.5
C4—C7—H7C109.5C14—C15—H15C109.5
H7A—C7—H7C109.5H15A—C15—H15C109.5
H7B—C7—H7C109.5H15B—C15—H15C109.5
N1—C8—C6122.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C9–C14 benzene ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.84 (4)1.84 (4)2.629 (3)154 (4)
C7—H7C···Cg1i0.962.913.767 (3)149
Symmetry code: (i) x+1/2, y+5/2, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C9–C14 benzene ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.84 (4)1.84 (4)2.629 (3)154 (4)
C7—H7C···Cg1i0.962.913.767 (3)149
Symmetry code: (i) x+1/2, y+5/2, z+1.
 

Acknowledgements

The author acknowledges Lishui University for financial support.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
First citationEbrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148–155.
First citationFan, C.-B., Wang, X.-M., Ding, P., Wang, J.-J., Liang, Z.-Q. & Tao, X.-T. (2012). Dyes Pigm. 95, 757–767.  Web of Science CSD CrossRef CAS
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSiddiqui, J. I., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206–211.  Web of Science CrossRef PubMed CAS

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ISSN: 2056-9890
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