2-[(E)-(Naphthalen-2-yl-imino)-meth-yl]-4-(trifluoro-meth-oxy)phenol.

In the title compound, C(18)H(12)F(3)NO(2), the planes of the benzene ring and the naphthalene system form a dihedral angle of 47.21 (3)°. The hy-droxy group is involved in an intra-molecular O-H⋯N hydrogen bond. In the crystal, weak C-H⋯O and C-H⋯F inter-actions link the mol-ecules related by translations along the c and a axes, respectively, into sheets.

Related literature

For background to photochromic and thermochromic characteristics and tautomerism of Schiff bases, see: Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶). For related structures, see: Gül et al. (2007 ▶); Yüce et al. (2004 ▶). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H12F3NO2

M = 331.29

Monoclinic,

a = 17.0813 (10) Å

b = 14.1248 (8) Å

c = 6.1900 (5) Å

β = 99.669 (6)°

V = 1472.25 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 123 K

0.50 × 0.40 × 0.18 mm

Data collection

Oxford Diffraction Gemini-R diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007 ▶) based on Clark & Reid (1995 ▶) T min = 0.941, T max = 0.978

15270 measured reflections

2892 independent reflections

2497 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.09

2892 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis PRO (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009361/cv5250sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009361/cv5250Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009361/cv5250Isup3.cml

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

C18H12F3NO2	F(000) = 680
Mr = 331.29	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5076 reflections
a = 17.0813 (10) Å	θ = 3.1–34.9°
b = 14.1248 (8) Å	µ = 0.12 mm−1
c = 6.1900 (5) Å	T = 123 K
β = 99.669 (6)°	Plate, yellow
V = 1472.25 (17) Å3	0.50 × 0.40 × 0.18 mm
Z = 4

Oxford Diffraction Gemini-R diffractometer	2892 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 10.5081 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −20→21
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007) based on Clark & Reid (1995)	k = −17→17
Tmin = 0.941, Tmax = 0.978	l = −7→6
15270 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.062P)2 + 0.5277P] where P = (Fo2 + 2Fc2)/3
2892 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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	0.52707 (9)	0.88417 (11)	0.3403 (3)	0.0225 (4)
C2	0.59465 (10)	0.90836 (11)	0.2604 (3)	0.0225 (3)
H2	0.5903	0.9338	0.1203	0.027*
C3	0.67071 (9)	0.89512 (10)	0.3876 (3)	0.0222 (3)
C4	0.74184 (10)	0.91509 (11)	0.3061 (3)	0.0268 (4)
H4	0.7390	0.9413	0.1672	0.032*
C5	0.81420 (10)	0.89635 (12)	0.4287 (3)	0.0313 (4)
H5	0.8601	0.9103	0.3729	0.038*
C6	0.82014 (11)	0.85608 (12)	0.6391 (3)	0.0320 (4)
H6	0.8698	0.8424	0.7201	0.038*
C7	0.75296 (10)	0.83705 (11)	0.7244 (3)	0.0275 (4)
H7	0.7573	0.8114	0.8642	0.033*
C8	0.67680 (10)	0.85604 (11)	0.6021 (3)	0.0232 (4)
C9	0.60574 (10)	0.83457 (11)	0.6822 (3)	0.0246 (4)
H9	0.6089	0.8110	0.8237	0.029*
C10	0.53290 (10)	0.84767 (11)	0.5564 (3)	0.0244 (4)
H10	0.4871	0.8327	0.6121	0.029*
C11	0.38798 (10)	0.90319 (11)	0.2662 (3)	0.0241 (4)
H11	0.3894	0.9215	0.4112	0.029*
C12	0.31186 (10)	0.89349 (11)	0.1221 (3)	0.0236 (4)
C13	0.24206 (10)	0.92206 (11)	0.1940 (3)	0.0246 (4)
H13	0.2443	0.9475	0.3334	0.030*
C14	0.17025 (10)	0.91238 (11)	0.0580 (3)	0.0265 (4)
C15	0.16428 (10)	0.87238 (12)	−0.1487 (3)	0.0285 (4)
H15	0.1150	0.8661	−0.2381	0.034*
C16	0.23260 (10)	0.84183 (12)	−0.2206 (3)	0.0279 (4)
H16	0.2290	0.8130	−0.3570	0.034*
C17	0.30663 (10)	0.85398 (11)	−0.0901 (3)	0.0248 (4)
C18	0.05121 (10)	0.89134 (14)	0.1960 (3)	0.0335 (4)
F1	0.08590 (7)	0.83013 (9)	0.3436 (2)	0.0551 (4)
F2	−0.00045 (7)	0.94076 (10)	0.2849 (2)	0.0537 (4)
F3	0.01029 (7)	0.84060 (11)	0.0357 (2)	0.0614 (4)
N1	0.45326 (8)	0.88684 (9)	0.1961 (2)	0.0241 (3)
O1	0.37203 (7)	0.82747 (9)	−0.1701 (2)	0.0301 (3)
O2	0.10202 (7)	0.95092 (8)	0.1277 (2)	0.0328 (3)
H1	0.4140 (16)	0.8422 (18)	−0.067 (5)	0.066 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0276 (8)	0.0185 (8)	0.0218 (8)	0.0017 (6)	0.0051 (7)	−0.0016 (6)
C2	0.0325 (9)	0.0176 (7)	0.0184 (8)	0.0003 (6)	0.0072 (7)	0.0002 (6)
C3	0.0282 (8)	0.0162 (7)	0.0228 (8)	0.0003 (6)	0.0060 (7)	−0.0030 (6)
C4	0.0327 (9)	0.0225 (8)	0.0268 (9)	−0.0017 (7)	0.0095 (7)	−0.0011 (7)
C5	0.0279 (9)	0.0273 (9)	0.0402 (10)	−0.0031 (7)	0.0102 (8)	−0.0038 (8)
C6	0.0299 (9)	0.0266 (9)	0.0370 (10)	0.0026 (7)	−0.0018 (8)	−0.0041 (8)
C7	0.0349 (9)	0.0205 (8)	0.0256 (9)	0.0014 (6)	0.0013 (7)	−0.0025 (6)
C8	0.0317 (9)	0.0158 (7)	0.0220 (8)	0.0005 (6)	0.0043 (7)	−0.0026 (6)
C9	0.0345 (9)	0.0215 (8)	0.0185 (8)	0.0009 (6)	0.0070 (7)	0.0011 (6)
C10	0.0282 (8)	0.0223 (8)	0.0253 (9)	−0.0004 (6)	0.0118 (7)	−0.0016 (6)
C11	0.0304 (9)	0.0207 (8)	0.0222 (8)	0.0005 (6)	0.0069 (7)	−0.0012 (6)
C12	0.0292 (8)	0.0191 (8)	0.0231 (8)	−0.0001 (6)	0.0063 (7)	0.0026 (6)
C13	0.0323 (9)	0.0191 (8)	0.0235 (8)	0.0006 (6)	0.0076 (7)	−0.0003 (6)
C14	0.0277 (8)	0.0224 (8)	0.0303 (9)	0.0020 (6)	0.0080 (7)	0.0031 (7)
C15	0.0291 (9)	0.0270 (8)	0.0282 (9)	−0.0026 (7)	0.0014 (7)	0.0036 (7)
C16	0.0350 (9)	0.0264 (8)	0.0221 (8)	−0.0016 (7)	0.0041 (7)	0.0003 (7)
C17	0.0303 (9)	0.0213 (8)	0.0245 (9)	−0.0010 (6)	0.0092 (7)	0.0010 (6)
C18	0.0257 (9)	0.0413 (11)	0.0330 (10)	0.0012 (7)	0.0035 (8)	−0.0022 (8)
F1	0.0503 (7)	0.0630 (8)	0.0554 (8)	0.0110 (6)	0.0188 (6)	0.0264 (6)
F2	0.0386 (7)	0.0587 (8)	0.0701 (9)	0.0065 (5)	0.0274 (6)	−0.0067 (6)
F3	0.0440 (7)	0.0829 (10)	0.0581 (8)	−0.0267 (7)	0.0108 (6)	−0.0259 (7)
N1	0.0275 (7)	0.0215 (7)	0.0236 (7)	−0.0009 (5)	0.0052 (6)	0.0006 (5)
O1	0.0299 (7)	0.0375 (7)	0.0244 (6)	0.0001 (5)	0.0085 (5)	−0.0058 (5)
O2	0.0283 (6)	0.0289 (7)	0.0428 (8)	0.0036 (5)	0.0103 (5)	−0.0008 (5)

C1—C2	1.373 (2)	C11—N1	1.284 (2)
C1—N1	1.417 (2)	C11—C12	1.454 (2)
C1—C10	1.421 (2)	C11—H11	0.9300
C2—C3	1.414 (2)	C12—C13	1.400 (2)
C2—H2	0.9300	C12—C17	1.416 (2)
C3—C4	1.420 (2)	C13—C14	1.373 (2)
C3—C8	1.425 (2)	C13—H13	0.9300
C4—C5	1.363 (2)	C14—C15	1.387 (2)
C4—H4	0.9300	C14—O2	1.4176 (19)
C5—C6	1.409 (3)	C15—C16	1.386 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.368 (3)	C16—C17	1.392 (2)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.416 (2)	C17—O1	1.349 (2)
C7—H7	0.9300	C18—F2	1.316 (2)
C8—C9	1.419 (2)	C18—F1	1.324 (2)
C9—C10	1.365 (2)	C18—F3	1.324 (2)
C9—H9	0.9300	C18—O2	1.328 (2)
C10—H10	0.9300	O1—H1	0.90 (3)
C2—C1—N1	118.63 (14)	N1—C11—C12	120.90 (15)
C2—C1—C10	119.94 (15)	N1—C11—H11	119.5
N1—C1—C10	121.10 (14)	C12—C11—H11	119.5
C1—C2—C3	121.05 (15)	C13—C12—C17	118.92 (15)
C1—C2—H2	119.5	C13—C12—C11	119.96 (15)
C3—C2—H2	119.5	C17—C12—C11	121.11 (15)
C2—C3—C4	122.47 (15)	C14—C13—C12	119.83 (15)
C2—C3—C8	119.10 (14)	C14—C13—H13	120.1
C4—C3—C8	118.35 (15)	C12—C13—H13	120.1
C5—C4—C3	120.90 (16)	C13—C14—C15	121.73 (15)
C5—C4—H4	119.6	C13—C14—O2	118.08 (15)
C3—C4—H4	119.6	C15—C14—O2	120.04 (15)
C4—C5—C6	120.71 (16)	C16—C15—C14	119.18 (16)
C4—C5—H5	119.6	C16—C15—H15	120.4
C6—C5—H5	119.6	C14—C15—H15	120.4
C7—C6—C5	120.07 (16)	C15—C16—C17	120.49 (16)
C7—C6—H6	120.0	C15—C16—H16	119.8
C5—C6—H6	120.0	C17—C16—H16	119.8
C6—C7—C8	120.76 (16)	O1—C17—C16	118.72 (15)
C6—C7—H7	119.6	O1—C17—C12	121.51 (15)
C8—C7—H7	119.6	C16—C17—C12	119.77 (15)
C7—C8—C9	122.39 (15)	F2—C18—F1	108.15 (15)
C7—C8—C3	119.20 (15)	F2—C18—F3	107.09 (14)
C9—C8—C3	118.38 (15)	F1—C18—F3	106.41 (17)
C10—C9—C8	121.55 (15)	F2—C18—O2	108.49 (16)
C10—C9—H9	119.2	F1—C18—O2	113.14 (14)
C8—C9—H9	119.2	F3—C18—O2	113.28 (15)
C9—C10—C1	119.93 (15)	C11—N1—C1	121.55 (14)
C9—C10—H10	120.0	C17—O1—H1	106.7 (17)
C1—C10—H10	120.0	C18—O2—C14	117.93 (13)
N1—C1—C2—C3	−171.57 (13)	C17—C12—C13—C14	−0.7 (2)
C10—C1—C2—C3	1.8 (2)	C11—C12—C13—C14	−179.68 (14)
C1—C2—C3—C4	176.90 (14)	C12—C13—C14—C15	1.8 (2)
C1—C2—C3—C8	0.0 (2)	C12—C13—C14—O2	−173.65 (14)
C2—C3—C4—C5	−176.17 (15)	C13—C14—C15—C16	−0.4 (2)
C8—C3—C4—C5	0.8 (2)	O2—C14—C15—C16	174.97 (14)
C3—C4—C5—C6	0.4 (3)	C14—C15—C16—C17	−2.1 (2)
C4—C5—C6—C7	−1.3 (3)	C15—C16—C17—O1	−176.85 (14)
C5—C6—C7—C8	1.0 (3)	C15—C16—C17—C12	3.2 (2)
C6—C7—C8—C9	178.00 (15)	C13—C12—C17—O1	178.27 (14)
C6—C7—C8—C3	0.2 (2)	C11—C12—C17—O1	−2.7 (2)
C2—C3—C8—C7	175.98 (14)	C13—C12—C17—C16	−1.8 (2)
C4—C3—C8—C7	−1.1 (2)	C11—C12—C17—C16	177.22 (14)
C2—C3—C8—C9	−1.9 (2)	C12—C11—N1—C1	−171.85 (13)
C4—C3—C8—C9	−178.95 (14)	C2—C1—N1—C11	−151.42 (15)
C7—C8—C9—C10	−175.68 (15)	C10—C1—N1—C11	35.3 (2)
C3—C8—C9—C10	2.1 (2)	F2—C18—O2—C14	170.19 (14)
C8—C9—C10—C1	−0.4 (2)	F1—C18—O2—C14	50.2 (2)
C2—C1—C10—C9	−1.6 (2)	F3—C18—O2—C14	−71.0 (2)
N1—C1—C10—C9	171.60 (14)	C13—C14—O2—C18	−105.77 (18)
N1—C11—C12—C13	−172.63 (14)	C15—C14—O2—C18	78.7 (2)
N1—C11—C12—C17	8.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90 (3)	1.77 (3)	2.5904 (18)	150 (2)
C10—H10···O1i	0.93	2.57	3.473 (2)	165
C5—H5···F2ii	0.93	2.57	3.487 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.90 (3)	1.77 (3)	2.5904 (18)	150 (2)
C10—H10⋯O1i	0.93	2.57	3.473 (2)	165
C5—H5⋯F2ii	0.93	2.57	3.487 (2)	170

Symmetry codes: (i) ; (ii) .