1-{(E)-[4-Bromo-2-(trifluoro-meth-oxy)phen-yl]imino-meth-yl}naphthalen-2-ol.

The title compound, C18H11BrF3NO2, crystallizes in the phenol-imine tautomeric form, with a strong intra-molecular O-H⋯N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 28.54 (10)°.

Related literature

For biological properties of Schiff bases, see: Layer (1963 ▶); Ingold (1969 ▶); Barton & Ollis (1979 ▶). For Schiff base tautom­erism, see: Hökelek et al. (2000 ▶); Tüfekçi et al. (2009 ▶). For related strucures, see: Bingöl Alpaslan et al. (2010 ▶); Soydemir et al. (2011 ▶).

Experimental

Crystal data

C18H11BrF3NO2

M = 410.19

Monoclinic,

a = 4.5315 (3) Å

b = 16.3228 (7) Å

c = 21.7622 (12) Å

β = 93.025 (4)°

V = 1607.44 (15) Å3

Z = 4

Mo Kα radiation

μ = 2.60 mm−1

T = 296 K

0.73 × 0.32 × 0.08 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.176, T max = 0.772

17993 measured reflections

3160 independent reflections

1932 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.092

S = 1.02

3160 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.20 e Å−3

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, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681300679X/bg2500sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300679X/bg2500Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300679X/bg2500Isup3.cml

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

C18H11BrF3NO2	F(000) = 816
Mr = 410.19	Dx = 1.695 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16693 reflections
a = 4.5315 (3) Å	θ = 1.6–27.3°
b = 16.3228 (7) Å	µ = 2.60 mm−1
c = 21.7622 (12) Å	T = 296 K
β = 93.025 (4)°	Needle, yellow
V = 1607.44 (15) Å3	0.73 × 0.32 × 0.08 mm
Z = 4

Stoe IPDS-II diffractometer	3160 independent reflections
Radiation source: fine-focus sealed tube	1932 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −20→20
Tmin = 0.176, Tmax = 0.772	l = −26→26
17993 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3
3160 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	1.2279 (8)	0.2342 (2)	0.35440 (16)	0.0573 (9)
C2	1.2003 (8)	0.3194 (3)	0.35626 (18)	0.0655 (10)
C3	1.3639 (10)	0.3657 (3)	0.4008 (2)	0.0776 (11)
H3	1.3428	0.4223	0.4018	0.093*
C4	1.5515 (9)	0.3281 (3)	0.44213 (19)	0.0765 (11)
H4	1.6587	0.3596	0.4710	0.092*
C5	1.5892 (8)	0.2423 (3)	0.44265 (17)	0.0657 (10)
C6	1.7837 (9)	0.2042 (3)	0.48585 (19)	0.0812 (12)
H6	1.8893	0.2362	0.5147	0.097*
C7	1.8217 (10)	0.1228 (4)	0.4867 (2)	0.0936 (14)
H7	1.9523	0.0986	0.5157	0.112*
C8	1.6626 (11)	0.0748 (3)	0.4434 (2)	0.0923 (14)
H8	1.6867	0.0182	0.4441	0.111*
C9	1.4735 (9)	0.1092 (3)	0.40055 (19)	0.0777 (11)
H9	1.3718	0.0759	0.3720	0.093*
C10	1.4281 (8)	0.1944 (2)	0.39847 (17)	0.0602 (9)
C11	1.0578 (8)	0.1889 (2)	0.30832 (17)	0.0622 (9)
H11	1.0735	0.1321	0.3078	0.075*
C12	0.7139 (8)	0.1804 (2)	0.22366 (16)	0.0597 (9)
C13	0.6122 (9)	0.1007 (3)	0.23012 (17)	0.0684 (10)
H13	0.6661	0.0716	0.2657	0.082*
C14	0.4340 (8)	0.0637 (3)	0.18521 (17)	0.0693 (10)
H14	0.3668	0.0104	0.1906	0.083*
C15	0.3558 (8)	0.1062 (2)	0.13217 (17)	0.0632 (10)
C16	0.4535 (8)	0.1847 (2)	0.12336 (17)	0.0648 (10)
H16	0.4010	0.2129	0.0873	0.078*
C17	0.6300 (8)	0.2206 (2)	0.16873 (18)	0.0609 (9)
C18	0.5876 (11)	0.3632 (3)	0.1640 (2)	0.0827 (12)
Br1	0.11465 (10)	0.05593 (3)	0.06926 (2)	0.08462 (18)
F1	0.4514 (8)	0.36567 (18)	0.21522 (15)	0.1282 (11)
F2	0.7514 (7)	0.42801 (17)	0.16068 (19)	0.1371 (12)
F3	0.3769 (6)	0.36943 (18)	0.11946 (14)	0.1162 (9)
N1	0.8849 (7)	0.22428 (19)	0.26788 (14)	0.0653 (8)
O1	1.0213 (7)	0.36180 (19)	0.31728 (16)	0.0838 (9)
O2	0.7558 (6)	0.29790 (17)	0.15836 (12)	0.0725 (7)
H1	0.963 (11)	0.327 (3)	0.290 (2)	0.12 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.062 (2)	0.055 (2)	0.055 (2)	−0.0034 (18)	0.0068 (18)	−0.0039 (17)
C2	0.069 (2)	0.063 (3)	0.065 (3)	0.002 (2)	0.009 (2)	−0.004 (2)
C3	0.089 (3)	0.058 (3)	0.086 (3)	−0.003 (2)	0.007 (2)	−0.015 (2)
C4	0.080 (3)	0.077 (3)	0.072 (3)	−0.012 (2)	−0.002 (2)	−0.018 (2)
C5	0.064 (2)	0.073 (3)	0.060 (2)	−0.003 (2)	0.0049 (19)	−0.008 (2)
C6	0.076 (3)	0.095 (4)	0.071 (3)	0.004 (3)	−0.007 (2)	−0.011 (2)
C7	0.093 (3)	0.109 (4)	0.077 (3)	0.021 (3)	−0.020 (2)	0.000 (3)
C8	0.117 (4)	0.070 (3)	0.088 (3)	0.015 (3)	−0.008 (3)	0.007 (3)
C9	0.099 (3)	0.063 (3)	0.069 (3)	0.006 (2)	−0.010 (2)	−0.006 (2)
C10	0.063 (2)	0.064 (3)	0.054 (2)	−0.0020 (19)	0.0071 (17)	−0.0050 (18)
C11	0.070 (2)	0.059 (3)	0.058 (2)	0.0022 (19)	0.0080 (19)	−0.0040 (19)
C12	0.063 (2)	0.062 (3)	0.054 (2)	0.0051 (19)	0.0022 (18)	−0.0035 (19)
C13	0.090 (3)	0.064 (3)	0.051 (2)	−0.005 (2)	−0.004 (2)	0.0055 (19)
C14	0.082 (2)	0.059 (2)	0.066 (2)	−0.008 (2)	0.0015 (19)	0.000 (2)
C15	0.069 (2)	0.064 (3)	0.056 (2)	0.0049 (19)	−0.0028 (18)	−0.0029 (19)
C16	0.069 (2)	0.065 (3)	0.059 (2)	0.004 (2)	−0.0098 (18)	0.007 (2)
C17	0.062 (2)	0.052 (2)	0.069 (2)	0.0020 (18)	0.0004 (19)	0.0051 (19)
C18	0.086 (3)	0.064 (3)	0.097 (4)	0.004 (3)	0.001 (3)	0.017 (3)
Br1	0.0931 (3)	0.0795 (3)	0.0783 (3)	−0.0037 (3)	−0.02406 (19)	−0.0046 (3)
F1	0.157 (3)	0.111 (2)	0.120 (2)	0.0348 (19)	0.034 (2)	−0.0057 (19)
F2	0.119 (2)	0.0595 (18)	0.230 (4)	−0.0058 (17)	−0.011 (2)	0.026 (2)
F3	0.1036 (19)	0.107 (2)	0.134 (2)	0.0219 (16)	−0.0291 (17)	0.0330 (18)
N1	0.0728 (19)	0.063 (2)	0.0594 (19)	0.0005 (16)	−0.0006 (16)	−0.0015 (16)
O1	0.103 (2)	0.063 (2)	0.084 (2)	0.0087 (17)	−0.0090 (18)	−0.0022 (17)
O2	0.0727 (16)	0.0599 (18)	0.0845 (19)	0.0017 (15)	0.0006 (14)	0.0078 (14)

C1—C2	1.397 (5)	C11—N1	1.284 (4)
C1—C11	1.437 (5)	C11—H11	0.9300
C1—C10	1.440 (5)	C12—C13	1.390 (5)
C2—O1	1.335 (5)	C12—C17	1.399 (5)
C2—C3	1.409 (6)	C12—N1	1.401 (5)
C3—C4	1.352 (6)	C13—C14	1.375 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.411 (6)	C14—C15	1.377 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.400 (6)	C15—C16	1.372 (5)
C5—C10	1.412 (5)	C15—Br1	1.893 (4)
C6—C7	1.339 (6)	C16—C17	1.369 (5)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.396 (6)	C17—O2	1.408 (4)
C7—H7	0.9300	C18—F2	1.297 (5)
C8—C9	1.356 (6)	C18—F1	1.302 (5)
C8—H8	0.9300	C18—O2	1.320 (5)
C9—C10	1.406 (5)	C18—F3	1.329 (5)
C9—H9	0.9300	O1—H1	0.85 (5)
C2—C1—C11	119.1 (3)	N1—C11—C1	122.2 (4)
C2—C1—C10	118.9 (3)	N1—C11—H11	118.9
C11—C1—C10	121.9 (3)	C1—C11—H11	118.9
O1—C2—C1	123.3 (4)	C13—C12—C17	116.7 (3)
O1—C2—C3	116.1 (4)	C13—C12—N1	125.7 (3)
C1—C2—C3	120.6 (4)	C17—C12—N1	117.5 (4)
C4—C3—C2	120.3 (4)	C14—C13—C12	121.7 (4)
C4—C3—H3	119.9	C14—C13—H13	119.2
C2—C3—H3	119.9	C12—C13—H13	119.2
C3—C4—C5	121.9 (4)	C13—C14—C15	119.3 (4)
C3—C4—H4	119.1	C13—C14—H14	120.3
C5—C4—H4	119.1	C15—C14—H14	120.3
C6—C5—C4	121.2 (4)	C16—C15—C14	121.2 (4)
C6—C5—C10	119.7 (4)	C16—C15—Br1	118.8 (3)
C4—C5—C10	119.0 (4)	C14—C15—Br1	120.0 (3)
C7—C6—C5	121.7 (4)	C17—C16—C15	118.7 (4)
C7—C6—H6	119.1	C17—C16—H16	120.7
C5—C6—H6	119.1	C15—C16—H16	120.7
C6—C7—C8	119.1 (4)	C16—C17—C12	122.5 (4)
C6—C7—H7	120.5	C16—C17—O2	119.6 (3)
C8—C7—H7	120.5	C12—C17—O2	117.6 (3)
C9—C8—C7	121.1 (5)	F2—C18—F1	108.7 (5)
C9—C8—H8	119.5	F2—C18—O2	108.6 (4)
C7—C8—H8	119.5	F1—C18—O2	114.1 (4)
C8—C9—C10	121.3 (4)	F2—C18—F3	106.7 (4)
C8—C9—H9	119.4	F1—C18—F3	105.5 (4)
C10—C9—H9	119.4	O2—C18—F3	113.0 (4)
C9—C10—C5	117.1 (4)	C11—N1—C12	122.4 (3)
C9—C10—C1	123.6 (4)	C2—O1—H1	104 (4)
C5—C10—C1	119.3 (4)	C18—O2—C17	117.9 (3)
C11—C1—C2—O1	0.3 (5)	C2—C1—C11—N1	1.4 (5)
C10—C1—C2—O1	179.8 (3)	C10—C1—C11—N1	−178.1 (3)
C11—C1—C2—C3	−180.0 (3)	C17—C12—C13—C14	−1.0 (5)
C10—C1—C2—C3	−0.5 (5)	N1—C12—C13—C14	177.0 (3)
O1—C2—C3—C4	−179.8 (4)	C12—C13—C14—C15	0.6 (6)
C1—C2—C3—C4	0.5 (6)	C13—C14—C15—C16	0.2 (5)
C2—C3—C4—C5	−0.5 (6)	C13—C14—C15—Br1	179.2 (3)
C3—C4—C5—C6	−179.8 (4)	C14—C15—C16—C17	−0.5 (5)
C3—C4—C5—C10	0.5 (6)	Br1—C15—C16—C17	−179.5 (3)
C4—C5—C6—C7	−179.9 (4)	C15—C16—C17—C12	−0.1 (5)
C10—C5—C6—C7	−0.1 (6)	C15—C16—C17—O2	174.0 (3)
C5—C6—C7—C8	−0.2 (7)	C13—C12—C17—C16	0.8 (5)
C6—C7—C8—C9	0.6 (7)	N1—C12—C17—C16	−177.4 (3)
C7—C8—C9—C10	−0.7 (7)	C13—C12—C17—O2	−173.3 (3)
C8—C9—C10—C5	0.4 (6)	N1—C12—C17—O2	8.4 (5)
C8—C9—C10—C1	−179.3 (4)	C1—C11—N1—C12	−178.6 (3)
C6—C5—C10—C9	0.0 (5)	C13—C12—N1—C11	27.1 (5)
C4—C5—C10—C9	179.8 (4)	C17—C12—N1—C11	−154.8 (3)
C6—C5—C10—C1	179.8 (3)	F2—C18—O2—C17	171.8 (4)
C4—C5—C10—C1	−0.5 (5)	F1—C18—O2—C17	50.4 (6)
C2—C1—C10—C9	−179.8 (3)	F3—C18—O2—C17	−70.0 (5)
C11—C1—C10—C9	−0.3 (5)	C16—C17—O2—C18	79.8 (5)
C2—C1—C10—C5	0.5 (5)	C12—C17—O2—C18	−105.9 (4)
C11—C1—C10—C5	180.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85 (5)	1.77 (6)	2.551 (5)	151 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85 (5)	1.77 (6)	2.551 (5)	151 (5)