1-{(E)-[(2-Fluoro-5-nitro-phen-yl)imino]-meth-yl}naphthalen-2-ol.

The title mol-ecule, C17H11FN2O3, is nearly planar [maximum deviation = 0.197 (1) Å] and the mol-ecular conformation is stabilized by an N-H⋯O hydrogen bond forming an S(6) ring motif. The H atom of the intra-molecular hydrogen bond was found to be disordered over two sites and thus both the hy-droxy and keto tautomers are simultaneously present in the solid. Refinement of the occupancy of this site suggests that the hy-droxy form is the major component [occupancy refined to 0.59 (3):0.41 (3)]. Bond lengths are also largely consistent with dominance of the hy-droxy form. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming layers parallel to (101). π-π stacking inter-actions [centroid-centroid distances = 3.5649 (9) and 3.7579 (9) Å] inter-connect these layers.

Related literature

For the broad range of biological applications of Schiff bases, see, for example: Cozzi (2004 ▶); Chandra & Sangeetika (2004 ▶); Sari et al. (2003 ▶); Verma et al. (2004 ▶). For the significance of fluorine atoms in drug structures, see: Blair et al. (2000 ▶); Kirk et al. (1979 ▶); LeBars et al. (1987 ▶). For a related structure, see: Akkurt et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H11FN2O3

M = 310.28

Monoclinic,

a = 14.2226 (6) Å

b = 13.0856 (5) Å

c = 7.3801 (3) Å

β = 94.151 (4)°

V = 1369.92 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 123 K

0.5 × 0.2 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.973, T max = 0.994

15943 measured reflections

4043 independent reflections

3166 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.135

S = 1.07

4043 reflections

215 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012099/sj5319sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012099/sj5319Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012099/sj5319Isup3.cml

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

C17H11FN2O3	F(000) = 640
Mr = 310.28	Dx = 1.504 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5692 reflections
a = 14.2226 (6) Å	θ = 3.2–30.7°
b = 13.0856 (5) Å	µ = 0.11 mm−1
c = 7.3801 (3) Å	T = 123 K
β = 94.151 (4)°	Cut rod, yellow
V = 1369.92 (10) Å3	0.5 × 0.2 × 0.05 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	4043 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3166 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 16.0727 pixels mm-1	θmax = 30.8°, θmin = 3.2°
ω scans	h = −19→20
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −18→18
Tmin = 0.973, Tmax = 0.994	l = −10→10
15943 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.7073P] where P = (Fo2 + 2Fc2)/3
4043 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.27 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
F1	0.46913 (7)	0.33478 (7)	0.24068 (14)	0.0300 (3)
O1	0.35134 (8)	0.12068 (8)	0.35743 (15)	0.0236 (3)
O2	0.21721 (11)	0.66754 (10)	0.5527 (3)	0.0535 (6)
O3	0.33368 (11)	0.75984 (10)	0.4783 (2)	0.0488 (5)
N1	0.31672 (9)	0.30387 (9)	0.41994 (17)	0.0185 (3)
N2	0.29390 (11)	0.67768 (10)	0.4896 (2)	0.0313 (4)
C1	0.21630 (10)	0.17180 (10)	0.51171 (19)	0.0171 (3)
C2	0.27574 (10)	0.09654 (11)	0.44206 (19)	0.0191 (4)
C3	0.25569 (11)	−0.00890 (11)	0.4642 (2)	0.0228 (4)
C4	0.18177 (11)	−0.03893 (11)	0.5579 (2)	0.0240 (4)
C5	0.11990 (11)	0.03344 (11)	0.6319 (2)	0.0215 (4)
C6	0.04339 (12)	0.00082 (13)	0.7289 (2)	0.0280 (5)
C7	−0.01858 (11)	0.06974 (13)	0.7933 (2)	0.0279 (5)
C8	−0.00642 (11)	0.17414 (13)	0.7622 (2)	0.0258 (4)
C9	0.06885 (10)	0.20868 (12)	0.6710 (2)	0.0221 (4)
C10	0.13476 (10)	0.13968 (11)	0.60456 (19)	0.0176 (3)
C11	0.24075 (10)	0.27705 (11)	0.49616 (18)	0.0177 (3)
C12	0.34637 (10)	0.40451 (10)	0.39717 (19)	0.0181 (3)
C13	0.42636 (10)	0.41877 (11)	0.3009 (2)	0.0212 (4)
C14	0.46365 (11)	0.51311 (13)	0.2649 (2)	0.0251 (4)
C15	0.42032 (11)	0.59926 (12)	0.3290 (2)	0.0247 (4)
C16	0.34099 (11)	0.58627 (11)	0.4245 (2)	0.0226 (4)
C17	0.30302 (10)	0.49186 (11)	0.4606 (2)	0.0200 (4)
H1	0.357 (3)	0.1877 (8)	0.365 (5)	0.0350*	0.59 (3)
H3	0.29440	−0.05880	0.41300	0.0270*
H4	0.17090	−0.10980	0.57460	0.0290*
H6	0.03470	−0.07010	0.74980	0.0340*
H7	−0.06960	0.04670	0.85880	0.0330*
H8	−0.05030	0.22180	0.80420	0.0310*
H9	0.07650	0.28000	0.65260	0.0260*
H11	0.20120	0.32800	0.54190	0.0210*
H14	0.51790	0.51890	0.19770	0.0300*
H15	0.44440	0.66560	0.30790	0.0300*
H17	0.24850	0.48650	0.52710	0.0240*
H2	0.350 (3)	0.253 (3)	0.380 (6)	0.0280*	0.41 (3)

	U11	U22	U33	U12	U13	U23
F1	0.0281 (5)	0.0236 (5)	0.0402 (6)	0.0041 (4)	0.0155 (4)	−0.0009 (4)
O1	0.0250 (5)	0.0173 (5)	0.0298 (6)	0.0025 (4)	0.0100 (4)	−0.0002 (4)
O2	0.0504 (9)	0.0238 (7)	0.0908 (12)	0.0049 (6)	0.0365 (9)	−0.0039 (7)
O3	0.0531 (9)	0.0143 (6)	0.0801 (11)	−0.0041 (6)	0.0128 (8)	−0.0018 (6)
N1	0.0198 (6)	0.0141 (6)	0.0220 (6)	0.0010 (4)	0.0038 (5)	0.0016 (4)
N2	0.0368 (8)	0.0152 (6)	0.0423 (8)	0.0018 (6)	0.0056 (7)	0.0009 (6)
C1	0.0186 (6)	0.0139 (6)	0.0187 (6)	0.0012 (5)	0.0011 (5)	−0.0005 (5)
C2	0.0217 (7)	0.0161 (6)	0.0193 (6)	0.0021 (5)	0.0007 (5)	0.0000 (5)
C3	0.0282 (8)	0.0148 (7)	0.0253 (7)	0.0024 (5)	0.0012 (6)	−0.0027 (5)
C4	0.0292 (8)	0.0141 (6)	0.0282 (8)	−0.0028 (6)	−0.0015 (6)	0.0004 (6)
C5	0.0227 (7)	0.0177 (7)	0.0236 (7)	−0.0033 (5)	−0.0012 (6)	0.0026 (5)
C6	0.0282 (8)	0.0256 (8)	0.0303 (8)	−0.0075 (6)	0.0023 (6)	0.0062 (6)
C7	0.0231 (7)	0.0336 (9)	0.0274 (8)	−0.0065 (6)	0.0051 (6)	0.0055 (7)
C8	0.0209 (7)	0.0309 (8)	0.0259 (7)	−0.0003 (6)	0.0048 (6)	−0.0006 (6)
C9	0.0220 (7)	0.0199 (7)	0.0246 (7)	−0.0004 (6)	0.0040 (6)	0.0003 (6)
C10	0.0186 (6)	0.0166 (6)	0.0175 (6)	−0.0021 (5)	0.0005 (5)	0.0009 (5)
C11	0.0179 (6)	0.0165 (6)	0.0186 (6)	0.0012 (5)	0.0016 (5)	−0.0009 (5)
C12	0.0179 (6)	0.0150 (6)	0.0213 (6)	−0.0006 (5)	0.0002 (5)	0.0023 (5)
C13	0.0204 (7)	0.0200 (7)	0.0234 (7)	0.0015 (5)	0.0040 (6)	−0.0001 (5)
C14	0.0196 (7)	0.0282 (8)	0.0280 (8)	−0.0043 (6)	0.0047 (6)	0.0049 (6)
C15	0.0240 (7)	0.0194 (7)	0.0305 (8)	−0.0062 (6)	0.0002 (6)	0.0061 (6)
C16	0.0249 (7)	0.0149 (7)	0.0279 (7)	0.0005 (5)	0.0006 (6)	0.0007 (5)
C17	0.0205 (7)	0.0159 (6)	0.0239 (7)	−0.0008 (5)	0.0036 (5)	0.0020 (5)

F1—C13	1.3471 (17)	C8—C9	1.381 (2)
O1—C2	1.3203 (18)	C9—C10	1.415 (2)
O2—N2	1.224 (2)	C12—C17	1.396 (2)
O3—N2	1.2206 (19)	C12—C13	1.397 (2)
O1—H1	0.882 (12)	C13—C14	1.377 (2)
N1—C12	1.3967 (18)	C14—C15	1.384 (2)
N1—C11	1.3019 (19)	C15—C16	1.383 (2)
N2—C16	1.469 (2)	C16—C17	1.382 (2)
N1—H2	0.88 (4)	C3—H3	0.9500
C1—C11	1.427 (2)	C4—H4	0.9500
C1—C2	1.418 (2)	C6—H6	0.9500
C1—C10	1.451 (2)	C7—H7	0.9500
C2—C3	1.421 (2)	C8—H8	0.9500
C3—C4	1.358 (2)	C9—H9	0.9500
C4—C5	1.428 (2)	C11—H11	0.9500
C5—C10	1.423 (2)	C14—H14	0.9500
C5—C6	1.411 (2)	C15—H15	0.9500
C6—C7	1.370 (2)	C17—H17	0.9500
C7—C8	1.398 (2)
C2—O1—H1	106 (3)	F1—C13—C12	117.56 (12)
C11—N1—C12	124.99 (13)	F1—C13—C14	118.58 (13)
O2—N2—C16	118.44 (13)	C12—C13—C14	123.86 (13)
O3—N2—C16	118.06 (15)	C13—C14—C15	118.48 (14)
O2—N2—O3	123.49 (15)	C14—C15—C16	118.27 (14)
C11—N1—H2	115 (3)	N2—C16—C15	118.34 (13)
C12—N1—H2	120 (3)	N2—C16—C17	118.12 (14)
C10—C1—C11	121.68 (12)	C15—C16—C17	123.54 (14)
C2—C1—C11	119.07 (13)	C12—C17—C16	118.64 (13)
C2—C1—C10	119.19 (12)	C2—C3—H3	120.00
C1—C2—C3	120.18 (13)	C4—C3—H3	120.00
O1—C2—C3	117.64 (13)	C3—C4—H4	119.00
O1—C2—C1	122.17 (13)	C5—C4—H4	119.00
C2—C3—C4	120.59 (14)	C5—C6—H6	119.00
C3—C4—C5	121.62 (13)	C7—C6—H6	119.00
C4—C5—C6	120.84 (14)	C6—C7—H7	120.00
C4—C5—C10	119.46 (13)	C8—C7—H7	120.00
C6—C5—C10	119.70 (14)	C7—C8—H8	120.00
C5—C6—C7	121.06 (15)	C9—C8—H8	120.00
C6—C7—C8	119.74 (15)	C8—C9—H9	119.00
C7—C8—C9	120.61 (15)	C10—C9—H9	119.00
C8—C9—C10	121.10 (14)	N1—C11—H11	120.00
C1—C10—C5	118.81 (13)	C1—C11—H11	120.00
C5—C10—C9	117.75 (13)	C13—C14—H14	121.00
C1—C10—C9	123.44 (13)	C15—C14—H14	121.00
N1—C11—C1	120.63 (13)	C14—C15—H15	121.00
N1—C12—C17	125.97 (13)	C16—C15—H15	121.00
N1—C12—C13	116.83 (12)	C12—C17—H17	121.00
C13—C12—C17	117.20 (13)	C16—C17—H17	121.00
C11—N1—C12—C17	3.8 (2)	C10—C5—C6—C7	1.8 (2)
C12—N1—C11—C1	179.56 (13)	C6—C5—C10—C1	177.21 (13)
C11—N1—C12—C13	−175.67 (14)	C4—C5—C6—C7	−177.11 (14)
O3—N2—C16—C15	−9.7 (2)	C4—C5—C10—C9	176.47 (14)
O3—N2—C16—C17	170.89 (15)	C6—C5—C10—C9	−2.4 (2)
O2—N2—C16—C15	170.52 (17)	C5—C6—C7—C8	0.3 (2)
O2—N2—C16—C17	−8.9 (2)	C6—C7—C8—C9	−1.6 (2)
C10—C1—C2—C3	−0.4 (2)	C7—C8—C9—C10	0.9 (2)
C2—C1—C11—N1	−0.3 (2)	C8—C9—C10—C1	−178.49 (14)
C10—C1—C2—O1	−179.51 (13)	C8—C9—C10—C5	1.1 (2)
C11—C1—C10—C9	6.1 (2)	N1—C12—C13—C14	179.10 (14)
C2—C1—C10—C5	3.5 (2)	C17—C12—C13—F1	179.39 (13)
C11—C1—C2—O1	−2.4 (2)	C17—C12—C13—C14	−0.5 (2)
C11—C1—C2—C3	176.71 (13)	N1—C12—C13—F1	−1.1 (2)
C11—C1—C10—C5	−173.49 (13)	N1—C12—C17—C16	−179.28 (14)
C10—C1—C11—N1	176.69 (13)	C13—C12—C17—C16	0.2 (2)
C2—C1—C10—C9	−176.87 (14)	F1—C13—C14—C15	−179.15 (13)
C1—C2—C3—C4	−2.5 (2)	C12—C13—C14—C15	0.7 (2)
O1—C2—C3—C4	176.68 (14)	C13—C14—C15—C16	−0.7 (2)
C2—C3—C4—C5	2.2 (2)	C14—C15—C16—N2	−178.86 (14)
C3—C4—C5—C10	1.1 (2)	C14—C15—C16—C17	0.5 (2)
C3—C4—C5—C6	179.98 (15)	N2—C16—C17—C12	179.10 (13)
C4—C5—C10—C1	−3.9 (2)	C15—C16—C17—C12	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.88 (1)	1.68 (2)	2.4969 (16)	152 (4)
C3—H3···O3i	0.95	2.48	3.222 (2)	135
C14—H14···O1ii	0.95	2.35	3.1724 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.88 (1)	1.68 (2)	2.4969 (16)	152 (4)
C3—H3⋯O3i	0.95	2.48	3.222 (2)	135
C14—H14⋯O1ii	0.95	2.35	3.1724 (19)	145

Symmetry codes: (i) ; (ii) .