Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022556/lx2009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022556/lx2009Isup2.hkl |
CCDC reference: 651437
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.112
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C7 .. 5.25 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The compound (E)-2-[(4-N,N-dimethylaminophenylimino)methyl] -6-methylphenol was prepared by reflux a mixture of a solution containing 3-methylsalicylaldehyde (0.1 ml 0.82 mmol) in 20 ml e thanol and a solution containing 4-N,N-dimethylphenylendiamin (0.14 g 0.82 mmol) in 20 ml e thanol. The reaction mixture was stirred for 1 h under reflux. The crystals of (E)-2-[(4-N,N-dimethylaminophenylimino)methyl]-6-methylphenol suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield % 38; m.p. 378–379 K).
The H1 atom was located in a difference map and refined freely. All other H atoms were placed in calculated positions and constrained to ride on their parents atoms, with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C).
Most Schiff bases have antibacterial, anticancer, antiinflammatory and antitoxic properties (Williams, 1972). In addition, Schiff bases are important in diverse fields of chemistry and biochemistry owing to their biological activites (Lozier et al., 1975; Garnovskii et al., 1993). Photochromism and thermochromism are also characteristics of these materials and arise via H-atom transfer from the hydroxy O atom to the N atom (Hadjoudis et al., 1987; Xu et al., 1994). These are two types of intra molecular hydrogen bonds in Schiff bases, in keto-amine (N—H···O) and phenol-imine (N···H—O) tautomeric forms. The present X-ray investigation shows that the title compound, (I), exists in the phenol-imine form (Fig.1).
Our investigations show that all bond lengths and angles are normal. The C8—N1 and C1—C7 bond lengths are 1.412 (2) and 1.441 (3) Å, respectively and agree with the corresponding distances in 1-{4-[(2-hydroxy-benzylidene)amino] phenyl}ethanone [1.4138 (17) and 1.4428 (18) Å; Yüce et al., 2004]. The N1═C7 bond length of 1.280 (2) Å is typical of a double bond, similar to the corresponding bond length in N-[3,5-Bis(trifluoromethyl)phenyl]salicylaldimine [1.276 (4) Å; Karadayı et al., 2003]. The O1—C6 distance of 1.350 (3) Å is close to the value of 1.352 (3) Å in (E)-2-[(3-trifluoromethylphenylimino)methyl]-4-methylphenol (Gül et al., 2007). The dihedral angle between the rings formed by atoms C1—C6 and C8—C13 is 7.86 (13)°. Fig.1 also shows a strong intramolecular hydrogen bond (O1—H1···N1) can be described as an S(6) motif (Bernstein et al., 1995). The O1—N1 distance of 2.574 (3) Å is comparable to those observed for analogous hydrogen bonds in 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone [2.5941 (15) Å; Yüce et al., 2004].
Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Cohen et al., 1964; Hadjoudis et al., 1987).
For related literature, see: Bernstein et al. (1995); Gül et al. (2007); Garnovskii et al. (1993); Karadayı, Gözüyeşil, Güzel & Büyükgüngör (2003); Lozier et al. (1975); Williams (1972); Xu et al. (1994); Yüce et al. (2004).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 40% probability level for non-H atoms. |
C16H18N2O | F(000) = 544 |
Mr = 254.32 | Dx = 1.193 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6157 reflections |
a = 8.3899 (9) Å | θ = 2.2–29.1° |
b = 6.0651 (4) Å | µ = 0.08 mm−1 |
c = 28.305 (3) Å | T = 296 K |
β = 100.502 (9)° | Prism, yellow |
V = 1416.2 (2) Å3 | 0.80 × 0.42 × 0.04 mm |
Z = 4 |
Stoe IPDS II diffractometer | 2784 independent reflections |
Radiation source: fine-focus sealed tube | 1105 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.085 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.5° |
ω scans | h = −10→10 |
Absorption correction: integration from crystal shape (X-RED32; Stoe & Cie, 2002) | k = −7→7 |
Tmin = 0.952, Tmax = 0.996 | l = −34→34 |
13978 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3 |
2784 reflections | (Δ/σ)max < 0.001 |
177 parameters | Δρmax = 0.10 e Å−3 |
0 restraints | Δρmin = −0.10 e Å−3 |
C16H18N2O | V = 1416.2 (2) Å3 |
Mr = 254.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3899 (9) Å | µ = 0.08 mm−1 |
b = 6.0651 (4) Å | T = 296 K |
c = 28.305 (3) Å | 0.80 × 0.42 × 0.04 mm |
β = 100.502 (9)° |
Stoe IPDS II diffractometer | 2784 independent reflections |
Absorption correction: integration from crystal shape (X-RED32; Stoe & Cie, 2002) | 1105 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.996 | Rint = 0.085 |
13978 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.82 | Δρmax = 0.10 e Å−3 |
2784 reflections | Δρmin = −0.10 e Å−3 |
177 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6175 (2) | 0.6277 (4) | 0.88499 (8) | 0.0785 (6) | |
C2 | 0.7394 (3) | 0.7759 (5) | 0.90267 (10) | 0.1035 (8) | |
H2 | 0.7608 | 0.8932 | 0.8836 | 0.124* | |
C3 | 0.8291 (3) | 0.7513 (6) | 0.94819 (12) | 0.1255 (11) | |
H3 | 0.9114 | 0.8504 | 0.9598 | 0.151* | |
C4 | 0.7955 (4) | 0.5784 (7) | 0.97624 (10) | 0.1163 (11) | |
H4 | 0.8567 | 0.5629 | 1.0069 | 0.140* | |
C5 | 0.6757 (3) | 0.4286 (5) | 0.96084 (9) | 0.1018 (9) | |
C6 | 0.5880 (3) | 0.4526 (5) | 0.91436 (8) | 0.0836 (7) | |
C7 | 0.5235 (2) | 0.6566 (4) | 0.83744 (8) | 0.0783 (6) | |
H7 | 0.5445 | 0.7773 | 0.8192 | 0.094* | |
C8 | 0.3122 (2) | 0.5455 (4) | 0.77405 (7) | 0.0651 (5) | |
C9 | 0.3143 (3) | 0.7199 (4) | 0.74297 (8) | 0.0810 (6) | |
H9 | 0.3916 | 0.8301 | 0.7508 | 0.097* | |
C10 | 0.2044 (3) | 0.7343 (4) | 0.70062 (8) | 0.0805 (6) | |
H10 | 0.2094 | 0.8538 | 0.6804 | 0.097* | |
C11 | 0.0858 (2) | 0.5740 (3) | 0.68735 (7) | 0.0659 (5) | |
C12 | 0.0882 (2) | 0.3937 (3) | 0.71795 (7) | 0.0716 (6) | |
H12 | 0.0146 | 0.2793 | 0.7098 | 0.086* | |
C13 | 0.1987 (2) | 0.3840 (3) | 0.76009 (8) | 0.0734 (6) | |
H13 | 0.1966 | 0.2627 | 0.7801 | 0.088* | |
C14 | −0.0300 (3) | 0.7795 (4) | 0.61455 (9) | 0.1074 (9) | |
H14A | −0.1177 | 0.7648 | 0.5877 | 0.161* | |
H14B | 0.0708 | 0.7862 | 0.6031 | 0.161* | |
H14C | −0.0441 | 0.9121 | 0.6318 | 0.161* | |
C15 | −0.1539 (3) | 0.4305 (4) | 0.63341 (9) | 0.0966 (7) | |
H15A | −0.2220 | 0.4710 | 0.6036 | 0.145* | |
H15B | −0.2178 | 0.4229 | 0.6583 | 0.145* | |
H15C | −0.1057 | 0.2893 | 0.6300 | 0.145* | |
C16 | 0.6370 (4) | 0.2447 (6) | 0.99256 (10) | 0.1431 (13) | |
H16A | 0.7109 | 0.2496 | 1.0227 | 0.215* | |
H16B | 0.6473 | 0.1057 | 0.9772 | 0.215* | |
H16C | 0.5280 | 0.2615 | 0.9980 | 0.215* | |
N1 | 0.41195 (19) | 0.5207 (3) | 0.81961 (6) | 0.0732 (5) | |
N2 | −0.0287 (2) | 0.5925 (3) | 0.64594 (6) | 0.0781 (5) | |
O1 | 0.4702 (2) | 0.3038 (3) | 0.89906 (8) | 0.1108 (6) | |
H1 | 0.439 (4) | 0.354 (5) | 0.8653 (14) | 0.169 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0598 (13) | 0.1073 (18) | 0.0686 (15) | 0.0066 (13) | 0.0119 (11) | −0.0091 (14) |
C2 | 0.0801 (17) | 0.140 (2) | 0.087 (2) | −0.0121 (16) | 0.0073 (15) | −0.0164 (16) |
C3 | 0.090 (2) | 0.182 (3) | 0.095 (2) | −0.002 (2) | −0.0073 (18) | −0.040 (2) |
C4 | 0.087 (2) | 0.184 (3) | 0.0726 (18) | 0.039 (2) | −0.0004 (16) | −0.026 (2) |
C5 | 0.0864 (17) | 0.144 (3) | 0.0718 (18) | 0.0399 (18) | 0.0065 (14) | −0.0058 (18) |
C6 | 0.0676 (14) | 0.111 (2) | 0.0711 (16) | 0.0220 (14) | 0.0087 (12) | −0.0001 (15) |
C7 | 0.0625 (13) | 0.1002 (17) | 0.0728 (16) | 0.0053 (13) | 0.0140 (12) | 0.0016 (12) |
C8 | 0.0571 (11) | 0.0760 (14) | 0.0612 (13) | 0.0012 (11) | 0.0084 (10) | 0.0033 (11) |
C9 | 0.0691 (14) | 0.0878 (16) | 0.0826 (16) | −0.0151 (11) | 0.0044 (12) | 0.0120 (13) |
C10 | 0.0778 (14) | 0.0846 (15) | 0.0757 (15) | −0.0138 (13) | 0.0048 (12) | 0.0241 (13) |
C11 | 0.0644 (12) | 0.0735 (14) | 0.0592 (12) | 0.0009 (11) | 0.0101 (10) | 0.0012 (11) |
C12 | 0.0739 (13) | 0.0657 (13) | 0.0717 (14) | −0.0097 (11) | 0.0044 (11) | 0.0089 (12) |
C13 | 0.0774 (13) | 0.0722 (14) | 0.0672 (13) | −0.0004 (12) | 0.0039 (11) | 0.0151 (11) |
C14 | 0.1044 (19) | 0.115 (2) | 0.0925 (19) | −0.0050 (15) | −0.0103 (15) | 0.0396 (16) |
C15 | 0.0992 (16) | 0.0915 (16) | 0.0869 (17) | −0.0078 (15) | −0.0150 (13) | −0.0023 (14) |
C16 | 0.165 (3) | 0.183 (3) | 0.078 (2) | 0.061 (2) | 0.014 (2) | 0.032 (2) |
N1 | 0.0570 (9) | 0.0914 (13) | 0.0684 (11) | 0.0052 (10) | 0.0045 (9) | 0.0014 (10) |
N2 | 0.0798 (11) | 0.0818 (12) | 0.0674 (11) | −0.0053 (10) | −0.0008 (9) | 0.0096 (10) |
O1 | 0.1058 (14) | 0.1237 (15) | 0.0945 (14) | −0.0067 (11) | −0.0040 (11) | 0.0253 (12) |
C1—C7 | 1.441 (3) | C10—C11 | 1.393 (3) |
C6—O1 | 1.350 (3) | C10—H10 | 0.9300 |
C7—N1 | 1.280 (2) | C11—N2 | 1.378 (2) |
C8—N1 | 1.412 (2) | C11—C12 | 1.393 (3) |
C1—C2 | 1.385 (3) | C12—C13 | 1.372 (3) |
C1—C6 | 1.398 (3) | C12—H12 | 0.9300 |
C2—C3 | 1.376 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—N2 | 1.439 (3) |
C3—C4 | 1.375 (4) | C14—H14A | 0.9600 |
C3—H3 | 0.9300 | C14—H14B | 0.9600 |
C4—C5 | 1.365 (4) | C14—H14C | 0.9600 |
C4—H4 | 0.9300 | C15—N2 | 1.435 (3) |
C5—C6 | 1.393 (3) | C15—H15A | 0.9600 |
C5—C16 | 1.504 (4) | C15—H15B | 0.9600 |
C7—H7 | 0.9300 | C15—H15C | 0.9600 |
C8—C13 | 1.373 (3) | C16—H16A | 0.9600 |
C8—C9 | 1.378 (3) | C16—H16B | 0.9600 |
C9—C10 | 1.375 (3) | C16—H16C | 0.9600 |
C9—H9 | 0.9300 | O1—H1 | 0.99 (4) |
C2—C1—C6 | 118.5 (2) | N2—C11—C10 | 121.7 (2) |
C2—C1—C7 | 120.0 (3) | C12—C11—C10 | 116.83 (19) |
C6—C1—C7 | 121.4 (2) | C13—C12—C11 | 120.4 (2) |
C3—C2—C1 | 120.6 (3) | C13—C12—H12 | 119.8 |
C3—C2—H2 | 119.7 | C11—C12—H12 | 119.8 |
C1—C2—H2 | 119.7 | C12—C13—C8 | 122.9 (2) |
C4—C3—C2 | 119.2 (3) | C12—C13—H13 | 118.6 |
C4—C3—H3 | 120.4 | C8—C13—H13 | 118.6 |
C2—C3—H3 | 120.4 | N2—C14—H14A | 109.5 |
C5—C4—C3 | 122.6 (3) | N2—C14—H14B | 109.5 |
C5—C4—H4 | 118.7 | H14A—C14—H14B | 109.5 |
C3—C4—H4 | 118.7 | N2—C14—H14C | 109.5 |
C4—C5—C6 | 117.6 (3) | H14A—C14—H14C | 109.5 |
C4—C5—C16 | 122.0 (3) | H14B—C14—H14C | 109.5 |
C6—C5—C16 | 120.4 (3) | N2—C15—H15A | 109.5 |
O1—C6—C5 | 117.6 (3) | N2—C15—H15B | 109.5 |
O1—C6—C1 | 121.1 (2) | H15A—C15—H15B | 109.5 |
C5—C6—C1 | 121.3 (3) | N2—C15—H15C | 109.5 |
N1—C7—C1 | 121.7 (2) | H15A—C15—H15C | 109.5 |
N1—C7—H7 | 119.1 | H15B—C15—H15C | 109.5 |
C1—C7—H7 | 119.1 | C5—C16—H16A | 109.5 |
C13—C8—C9 | 116.9 (2) | C5—C16—H16B | 109.5 |
C13—C8—N1 | 116.8 (2) | H16A—C16—H16B | 109.5 |
C9—C8—N1 | 126.2 (2) | C5—C16—H16C | 109.5 |
C10—C9—C8 | 121.4 (2) | H16A—C16—H16C | 109.5 |
C10—C9—H9 | 119.3 | H16B—C16—H16C | 109.5 |
C8—C9—H9 | 119.3 | C7—N1—C8 | 124.1 (2) |
C9—C10—C11 | 121.5 (2) | C11—N2—C15 | 121.32 (19) |
C9—C10—H10 | 119.2 | C11—N2—C14 | 121.0 (2) |
C11—C10—H10 | 119.2 | C15—N2—C14 | 117.7 (2) |
N2—C11—C12 | 121.5 (2) | C6—O1—H1 | 98.8 (19) |
C6—C1—C2—C3 | −0.1 (3) | N1—C8—C9—C10 | −175.8 (2) |
C7—C1—C2—C3 | 179.4 (2) | C8—C9—C10—C11 | 0.3 (3) |
C1—C2—C3—C4 | −0.6 (4) | C9—C10—C11—N2 | 177.2 (2) |
C2—C3—C4—C5 | −0.1 (4) | C9—C10—C11—C12 | −2.8 (3) |
C3—C4—C5—C6 | 1.4 (4) | N2—C11—C12—C13 | −176.96 (19) |
C3—C4—C5—C16 | −178.0 (3) | C10—C11—C12—C13 | 3.0 (3) |
C4—C5—C6—O1 | 179.6 (2) | C11—C12—C13—C8 | −0.9 (3) |
C16—C5—C6—O1 | −1.0 (3) | C9—C8—C13—C12 | −1.6 (3) |
C4—C5—C6—C1 | −2.0 (3) | N1—C8—C13—C12 | 176.32 (18) |
C16—C5—C6—C1 | 177.3 (2) | C1—C7—N1—C8 | 177.48 (18) |
C2—C1—C6—O1 | 179.7 (2) | C13—C8—N1—C7 | 179.63 (18) |
C7—C1—C6—O1 | 0.2 (3) | C9—C8—N1—C7 | −2.7 (3) |
C2—C1—C6—C5 | 1.5 (3) | C12—C11—N2—C15 | 2.2 (3) |
C7—C1—C6—C5 | −178.1 (2) | C10—C11—N2—C15 | −177.8 (2) |
C2—C1—C7—N1 | 178.7 (2) | C12—C11—N2—C14 | −179.94 (19) |
C6—C1—C7—N1 | −1.8 (3) | C10—C11—N2—C14 | 0.1 (3) |
C13—C8—C9—C10 | 1.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.99 (4) | 1.62 (4) | 2.574 (3) | 159 (3) |
Experimental details
Crystal data | |
Chemical formula | C16H18N2O |
Mr | 254.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 8.3899 (9), 6.0651 (4), 28.305 (3) |
β (°) | 100.502 (9) |
V (Å3) | 1416.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.80 × 0.42 × 0.04 |
Data collection | |
Diffractometer | Stoe IPDS II |
Absorption correction | Integration from crystal shape (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.952, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13978, 2784, 1105 |
Rint | 0.085 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.112, 0.82 |
No. of reflections | 2784 |
No. of parameters | 177 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.10, −0.10 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.99 (4) | 1.62 (4) | 2.574 (3) | 159 (3) |
Most Schiff bases have antibacterial, anticancer, antiinflammatory and antitoxic properties (Williams, 1972). In addition, Schiff bases are important in diverse fields of chemistry and biochemistry owing to their biological activites (Lozier et al., 1975; Garnovskii et al., 1993). Photochromism and thermochromism are also characteristics of these materials and arise via H-atom transfer from the hydroxy O atom to the N atom (Hadjoudis et al., 1987; Xu et al., 1994). These are two types of intra molecular hydrogen bonds in Schiff bases, in keto-amine (N—H···O) and phenol-imine (N···H—O) tautomeric forms. The present X-ray investigation shows that the title compound, (I), exists in the phenol-imine form (Fig.1).
Our investigations show that all bond lengths and angles are normal. The C8—N1 and C1—C7 bond lengths are 1.412 (2) and 1.441 (3) Å, respectively and agree with the corresponding distances in 1-{4-[(2-hydroxy-benzylidene)amino] phenyl}ethanone [1.4138 (17) and 1.4428 (18) Å; Yüce et al., 2004]. The N1═C7 bond length of 1.280 (2) Å is typical of a double bond, similar to the corresponding bond length in N-[3,5-Bis(trifluoromethyl)phenyl]salicylaldimine [1.276 (4) Å; Karadayı et al., 2003]. The O1—C6 distance of 1.350 (3) Å is close to the value of 1.352 (3) Å in (E)-2-[(3-trifluoromethylphenylimino)methyl]-4-methylphenol (Gül et al., 2007). The dihedral angle between the rings formed by atoms C1—C6 and C8—C13 is 7.86 (13)°. Fig.1 also shows a strong intramolecular hydrogen bond (O1—H1···N1) can be described as an S(6) motif (Bernstein et al., 1995). The O1—N1 distance of 2.574 (3) Å is comparable to those observed for analogous hydrogen bonds in 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone [2.5941 (15) Å; Yüce et al., 2004].