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

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ISSN: 2414-3146

2-{(E)-[(3-Chloro-4-methyl­phen­yl)imino]­meth­yl}-4-(tri­fluoro­meth­­oxy)phenol

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aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, 55139 Samsun, Turkey, and bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, 55139 Samsun, Turkey
*Correspondence e-mail: atalays@omu.edu.tr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 November 2017; accepted 1 December 2017; online 12 December 2017)

In the title compound, C15H11ClF3NO2, the dihedral angle between the planes of the benzene rings is 8.3 (2)° and an intra­molecular O—H⋯N hydrogen bond closes an S(6) ring. In the crystal, weak C—H⋯O links connect the mol­ecules into [-110] chains. The F atoms of the CF3 group are disordered over two sets of sites with refined occupancies of 0.626 (11):0.374 (11).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

We herein report the synthesis and structure of the new Schiff base (Fig. 1[link]). The bond distances of the imino group atoms [N1–C9 = 1.423 (5); N1—C8 = 1.275 (5) Å] are consistent with those in the related structures 2-[(2- bromo­phen­yl)imino­meth­yl]-6-methyl­phenol (Karadağ et al., 2010[Karadağ, A. T,, Atalay, Ş. & Genç, H. (2010). Acta Cryst. E66, o2977.]) and 2-amino-3-((E)-{[3-(tri­fluoro­meth­yl)phen­yl]imino}-meth­yl)-4H-chromen-4-one (Atalay et al., 2016[Atalay, Ş., Gerçeker, S., Meral, S. & Alaman Ağar, A. (2016). IUCrData, 1, x160797.]). The dihedral angle between the benzene rings is 8.3 (2)° and an intra­molecular O—H⋯N hydrogen bond (Table 1[link]) closes an S(6) ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯N1 0.82 1.88 2.609 (5) 148
C10—H10⋯O2i 0.93 2.52 3.277 (5) 139
Symmetry code: (i) x-1, y+1, z.
[Figure 1]
Figure 1
The mol­ecular structure showing 30% probability displacement ellipsoids. Only the major-disorder component of the CF3 group is shown.

In the crystal (Fig. 2[link]), weak C—H⋯O links connect the mol­ecules into [[\overline{1}]10] chains.

[Figure 2]
Figure 2
The packing, viewed along [100] with hydrogen bonds shown as dashed lines..

Synthesis and crystallization

A mixture of 2-hy­droxy-5-(tri­fluoro­meth­oxy)benzaldehyde (0.19 g, 0.9 mol) in ethanol (20 ml) and 3-chloro-4-methyaniline (0.13 g, 0.9 mol) in ethanol (20 ml) were mixed and stirred for 5 h under reflux. Light-yellow plate-shaped crystals were obtained by slow evaporation of an ethanol solution (yield 67%; m.p. 361–363 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The F atoms of the CF3 group are disordered over two sets of sites with refined occupancies of 0.626 (11):0.374 (11).

Table 2
Experimental details

Crystal data
Chemical formula C15H11ClF3NO2
Mr 329.70
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 4.5971 (4), 6.4372 (7), 25.237 (2)
α, β, γ (°) 86.984 (8), 86.173 (7), 78.096 (8)
V3) 728.57 (12)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.30
Crystal size (mm) 0.42 × 0.24 × 0.05
 
Data collection
Diffractometer Stoe IPDS 2
Absorption correction Integration (X-AREA; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.907, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections 6174, 2581, 1173
Rint 0.050
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.181, 0.89
No. of reflections 2581
No. of parameters 228
No. of restraints 96
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.44, −0.29
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SHELXT2016 (Sheldrick, 2015[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data


Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

2-{(E)-[(3-Chloro-4-methylphenyl)imino]methyl}-4-(trifluoromethoxy)phenol top
Crystal data top
C15H11ClF3NO2Z = 2
Mr = 329.70F(000) = 336
Triclinic, P1Dx = 1.503 Mg m3
a = 4.5971 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.4372 (7) ÅCell parameters from 4834 reflections
c = 25.237 (2) Åθ = 1.6–27.4°
α = 86.984 (8)°µ = 0.30 mm1
β = 86.173 (7)°T = 293 K
γ = 78.096 (8)°Plate, light yellow
V = 728.57 (12) Å30.42 × 0.24 × 0.05 mm
Data collection top
Stoe IPDS 2
diffractometer
1173 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.050
rotation method scansθmax = 25.0°, θmin = 1.6°
Absorption correction: integration
(X-AREA; Stoe & Cie, 2002)
h = 55
Tmin = 0.907, Tmax = 0.986k = 77
6174 measured reflectionsl = 2929
2581 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.098P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
2581 reflectionsΔρmax = 0.44 e Å3
228 parametersΔρmin = 0.29 e Å3
96 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. The H atoms attached to C10 and C16 were placed in calculated positions and refined using a riding model, with C–H distances of 0.93 Å and methyl C–H distances 0.96 Å. All other H atoms were freely refined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C11.2010 (15)0.7569 (14)0.5585 (3)0.1286 (17)
C21.2114 (9)0.5356 (8)0.63470 (17)0.0694 (12)
C30.9931 (9)0.6027 (7)0.67272 (17)0.0691 (11)
H30.9147640.7470800.6757660.083*
C40.8865 (8)0.4547 (6)0.70721 (15)0.0595 (10)
C51.0128 (9)0.2385 (7)0.70263 (17)0.0676 (11)
C61.2400 (11)0.1773 (8)0.6644 (2)0.0847 (13)
H61.3274120.0341170.6618990.102*
C71.3387 (10)0.3233 (8)0.63015 (19)0.0795 (13)
H71.4893590.2799520.6042090.095*
C80.6507 (9)0.5284 (7)0.74676 (16)0.0647 (11)
H80.5773590.6738190.7488660.078*
C90.3055 (8)0.4808 (7)0.81702 (15)0.0609 (10)
C100.1480 (9)0.6892 (7)0.81789 (17)0.0704 (12)
H100.1906700.7888030.7920700.084*
C110.0704 (9)0.7473 (7)0.85695 (18)0.0736 (12)
H110.1719750.8881280.8568660.088*
C120.1488 (9)0.6093 (7)0.89651 (16)0.0658 (11)
C130.0067 (9)0.4005 (7)0.89411 (16)0.0660 (11)
C140.2288 (9)0.3368 (7)0.85488 (17)0.0663 (11)
H140.3269000.1952680.8541760.080*
C150.3891 (10)0.6817 (8)0.93910 (18)0.0837 (13)
H15A0.4678960.8308500.9336910.125*
H15B0.3065940.6557890.9733580.125*
H15C0.5456470.6043980.9373550.125*
Cl10.0746 (3)0.2116 (2)0.94138 (5)0.0940 (5)
F1A1.229 (3)0.6214 (16)0.5215 (3)0.150 (3)0.374 (11)
F2A1.287 (4)0.918 (3)0.5377 (6)0.141 (3)0.374 (11)
F3A0.8893 (14)0.837 (3)0.5742 (4)0.145 (3)0.374 (11)
F1B1.036 (2)0.6539 (13)0.5373 (3)0.139 (2)0.626 (11)
F2B1.335 (2)0.8762 (19)0.5297 (4)0.151 (3)0.626 (11)
F3B0.9360 (13)0.9123 (13)0.5759 (2)0.142 (2)0.626 (11)
N10.5390 (7)0.4024 (5)0.77887 (13)0.0641 (9)
O11.3285 (6)0.6855 (5)0.60186 (13)0.0859 (10)
O20.9184 (7)0.0908 (5)0.73535 (13)0.0896 (10)
H20.7830640.1490110.7556970.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.108 (3)0.180 (4)0.111 (4)0.070 (3)0.009 (3)0.039 (3)
C20.059 (3)0.083 (3)0.069 (3)0.021 (2)0.005 (2)0.003 (2)
C30.062 (3)0.069 (3)0.076 (3)0.011 (2)0.008 (2)0.002 (2)
C40.058 (2)0.055 (2)0.064 (2)0.008 (2)0.009 (2)0.003 (2)
C50.068 (3)0.057 (3)0.075 (3)0.004 (2)0.007 (2)0.003 (2)
C60.083 (3)0.070 (3)0.096 (3)0.003 (3)0.001 (3)0.013 (3)
C70.068 (3)0.083 (4)0.084 (3)0.007 (3)0.003 (2)0.014 (3)
C80.060 (2)0.057 (3)0.074 (3)0.004 (2)0.008 (2)0.006 (2)
C90.056 (2)0.066 (3)0.061 (2)0.012 (2)0.010 (2)0.001 (2)
C100.074 (3)0.063 (3)0.070 (3)0.006 (2)0.003 (2)0.003 (2)
C110.066 (3)0.065 (3)0.084 (3)0.002 (2)0.003 (2)0.006 (2)
C120.064 (3)0.072 (3)0.064 (3)0.014 (2)0.012 (2)0.011 (2)
C130.066 (3)0.070 (3)0.064 (3)0.019 (2)0.008 (2)0.000 (2)
C140.062 (3)0.058 (3)0.077 (3)0.006 (2)0.010 (2)0.000 (2)
C150.077 (3)0.092 (3)0.081 (3)0.013 (3)0.002 (3)0.016 (3)
Cl10.1027 (9)0.0869 (9)0.0912 (9)0.0253 (7)0.0124 (7)0.0085 (7)
F1A0.155 (6)0.217 (5)0.097 (5)0.082 (5)0.017 (4)0.019 (4)
F2A0.113 (5)0.177 (5)0.134 (5)0.053 (5)0.002 (5)0.062 (4)
F3A0.104 (4)0.189 (7)0.145 (5)0.054 (4)0.019 (4)0.064 (5)
F1B0.134 (4)0.203 (5)0.096 (4)0.075 (3)0.024 (3)0.023 (3)
F2B0.125 (4)0.204 (5)0.128 (4)0.065 (4)0.003 (3)0.072 (4)
F3B0.116 (3)0.171 (5)0.144 (4)0.050 (3)0.017 (3)0.050 (3)
N10.061 (2)0.065 (2)0.065 (2)0.0095 (17)0.0083 (17)0.0029 (17)
O10.0700 (19)0.104 (3)0.084 (2)0.0227 (18)0.0023 (16)0.0140 (19)
O20.100 (2)0.0600 (19)0.098 (2)0.0005 (17)0.0112 (19)0.0085 (17)
Geometric parameters (Å, º) top
C1—F2B1.255 (7)C8—N11.275 (5)
C1—F2A1.263 (7)C8—H80.9300
C1—F1B1.267 (8)C9—C141.376 (5)
C1—O11.293 (7)C9—C101.387 (6)
C1—F1A1.293 (8)C9—N11.423 (5)
C1—F3A1.455 (9)C10—C111.368 (6)
C1—F3B1.466 (8)C10—H100.9300
C2—C31.360 (6)C11—C121.381 (6)
C2—C71.379 (6)C11—H110.9300
C2—O11.406 (5)C12—C131.388 (6)
C3—C41.398 (5)C12—C151.508 (6)
C3—H30.9300C13—C141.388 (6)
C4—C51.401 (6)C13—Cl11.737 (4)
C4—C81.446 (5)C14—H140.9300
C5—O21.347 (5)C15—H15A0.9600
C5—C61.383 (6)C15—H15B0.9600
C6—C71.369 (6)C15—H15C0.9600
C6—H60.9300O2—H20.8200
C7—H70.9300
F2B—C1—F1B119.1 (8)N1—C8—C4122.7 (4)
F2B—C1—O1114.6 (6)N1—C8—H8118.6
F2A—C1—O1113.5 (7)C4—C8—H8118.6
F1B—C1—O1120.7 (7)C14—C9—C10118.4 (4)
F2A—C1—F1A106.5 (12)C14—C9—N1116.9 (4)
O1—C1—F1A115.4 (7)C10—C9—N1124.7 (4)
F2A—C1—F3A103.6 (12)C11—C10—C9119.6 (4)
O1—C1—F3A105.9 (6)C11—C10—H10120.2
F1A—C1—F3A111.4 (10)C9—C10—H10120.2
F2B—C1—F3B99.7 (9)C10—C11—C12123.9 (4)
F1B—C1—F3B89.5 (6)C10—C11—H11118.1
O1—C1—F3B104.8 (6)C12—C11—H11118.1
C3—C2—C7121.5 (4)C11—C12—C13115.5 (4)
C3—C2—O1119.8 (4)C11—C12—C15121.9 (4)
C7—C2—O1118.5 (4)C13—C12—C15122.6 (4)
C2—C3—C4120.0 (4)C14—C13—C12121.9 (4)
C2—C3—H3120.0C14—C13—Cl1118.4 (3)
C4—C3—H3120.0C12—C13—Cl1119.8 (3)
C3—C4—C5118.9 (4)C9—C14—C13120.7 (4)
C3—C4—C8119.3 (4)C9—C14—H14119.6
C5—C4—C8121.8 (4)C13—C14—H14119.6
O2—C5—C6119.9 (4)C12—C15—H15A109.5
O2—C5—C4120.8 (4)C12—C15—H15B109.5
C6—C5—C4119.3 (4)H15A—C15—H15B109.5
C7—C6—C5121.3 (5)C12—C15—H15C109.5
C7—C6—H6119.3H15A—C15—H15C109.5
C5—C6—H6119.3H15B—C15—H15C109.5
C6—C7—C2119.0 (5)C8—N1—C9121.1 (4)
C6—C7—H7120.5C1—O1—C2119.2 (4)
C2—C7—H7120.5C5—O2—H2109.5
C7—C2—C3—C42.0 (6)C11—C12—C13—C140.9 (6)
O1—C2—C3—C4176.8 (4)C15—C12—C13—C14179.5 (4)
C2—C3—C4—C51.5 (6)C11—C12—C13—Cl1179.4 (3)
C2—C3—C4—C8178.9 (4)C15—C12—C13—Cl10.2 (6)
C3—C4—C5—O2179.4 (4)C10—C9—C14—C132.3 (6)
C8—C4—C5—O20.2 (6)N1—C9—C14—C13179.0 (3)
C3—C4—C5—C60.3 (6)C12—C13—C14—C90.8 (6)
C8—C4—C5—C6179.3 (4)Cl1—C13—C14—C9178.9 (3)
O2—C5—C6—C7179.3 (4)C4—C8—N1—C9179.5 (3)
C4—C5—C6—C71.6 (7)C14—C9—N1—C8170.8 (4)
C5—C6—C7—C21.1 (7)C10—C9—N1—C810.6 (6)
C3—C2—C7—C60.7 (7)F2B—C1—O1—C2174.4 (10)
O1—C2—C7—C6175.6 (4)F2A—C1—O1—C2167.0 (13)
C3—C4—C8—N1178.7 (4)F1B—C1—O1—C221.0 (11)
C5—C4—C8—N11.6 (6)F1A—C1—O1—C269.7 (10)
C14—C9—C10—C112.1 (6)F3A—C1—O1—C254.0 (11)
N1—C9—C10—C11179.2 (4)F3B—C1—O1—C277.4 (7)
C9—C10—C11—C120.4 (7)C3—C2—O1—C187.8 (6)
C10—C11—C12—C131.1 (6)C7—C2—O1—C197.2 (6)
C10—C11—C12—C15179.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.882.609 (5)148
C10—H10···O2i0.932.523.277 (5)139
Symmetry code: (i) x1, y+1, z.
 

Funding information

The authors thank the Turkish Government and Ondokuz Mayıs University for research grant PYO·FEN.1904.16.005.

References

First citationAtalay, Ş., Gerçeker, S., Meral, S. & Alaman Ağar, A. (2016). IUCrData, 1, x160797.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationKaradağ, A. T,, Atalay, Ş. & Genç, H. (2010). Acta Cryst. E66, o2977.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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