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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 9| September 2012| Page o2779
doi:10.1107/S1600536812034824

(E)-1-[(3-Bromo­phen­yl)imino­meth­yl]naphthalen-2-ol

Tufan Akbal,a* Ayşen Ağar Alaman,b Sümeyye Gümüşb and Ahmet Erdönmeza

aOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, and bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Chemistry, 55139 Samsun, Turkey
*Correspondence e-mail: takbal@omu.edu.tr

(Received 31 July 2012; accepted 6 August 2012; online 25 August 2012)

The title compound, C17H12BrNO, exists in an enol–imine form and the mol­ecular structure features an intra­molecular O—H⋯N hydrogen bond. The dihedral angle between the benzene ring and the naphthalene ring system is 17.27 (15)°.

Related literature

For general background to and applications of Schiff bases, see: Garnovski et al. (1993[Garnovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1-69.]); Hamilton et al. (1987[Hamilton, D. E., Drago, R. S. & Zombeck, A. (1987). J. Am. Chem. Soc. 109, 374-379.]); Pyrz et al. (1985[Pyrz, J. W., Roe, A. L., Stern, L. J. & Que, L. Jr (1985). J. Am. Chem. Soc. 107, 614-620.]); Costamagna et al. (1992[Costamagna, J., Vargas, J., Latorre, R., Alvarado, A. & Mena, G. (1992). Coord. Chem. Rev. 119, 67-88.]). For a related structure, see: Ünver et al. (2000[Ünver, H., Zengin, D. M. & Güven, K. (2000). J. Chem. Crystallogr. 30, 359-364.]).

[Scheme 1]

Experimental

Crystal data

  • C17H12BrNO

  • Mr = 326.19

  • Monoclinic, C 2/c

  • a = 31.3965 (19) Å

  • b = 4.8657 (2) Å

  • c = 19.0124 (11) Å

  • β = 107.772 (4)°

  • V = 2765.8 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.97 mm−1

  • T = 296 K

  • 0.80 × 0.36 × 0.13 mm
Data collection

  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.421, Tmax = 0.680

  • 14469 measured reflections

  • 2706 independent reflections

  • 1992 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.117

  • S = 1.02

  • 2706 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯N1 0.82 1.82 2.548 (4) 147

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812034824/is5182sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034824/is5182Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034824/is5182Isup3.mol

Supporting information file. DOI: 10.1107/S1600536812034824/is5182Isup4.cml

checkCIF report


Comment top

Schiff bases from 2-hydroxy-1-naphthaldehyde have often been used as chelating ligands in the field coordination chemistry (Garnovski et al., 1993). The Schiff base complexes have also been used in catalytic reactions (Hamilton et al., 1987) and used as models for biological systems (Pyrz et al., 1985; Costamagna et al., 1992). There are two types of intramolecular hydrogen bonds in Schiff bases, namely keto-amine (N—H···O) and enol-imine (N···H—O) tautomeric forms.

The present X-ray investigation shows that the title compound, (I), prefers the enol-imine tautomeric form rather than the keto-amine tautomeric form (Fig. 1). The C9—O1 and C7—N1 bond lengths verify the enol-imine tautomeric form; these distances agree with the literature [1.310 (8) and 1.319 (6) Å; Ünver et al., 2000], which also shows the enol-imine tautomeric form. The C6—Br1 bond length in (I) is also in a good agreement with the corresponding distance in the literature [1.904 (2) Å; Ünver et al., 2000]. The molecule is non-planar. The dihedral angle between the two Schiff base moieties (C1–C6/N1) and (C7–C13/O1) is 16.27 (12)°. A view of the crystal packing of the title compound is shown in Fig. 2. π–π interactions between the centroids of the Cg1 and Cg2 rings [distance between ring centroids = 4.6002 (19) Å], and the Cg2 and Cg3 rings [distance between ring centroids = 4.805 (2) Å], stack the molecules along the b-axis. Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C12–C17 rings, respectively.

Related literature top

For general background to and applications of Schiff bases, see: Garnovski et al. (1993); Hamilton et al. (1987); Pyrz et al. (1985); Costamagna et al. (1992). For a related structure, see: Ünver et al. (2000).

Experimental top

The compound (E)-1-[(3-bromophenyllimino)methyl]naphthalen-2-ol was prepared by refluxing a mixture of a solution containing 2-hydroxy-1-naphthaldehyde (17.2 mg, 0.100 mmol) in 30 ml absolute ethanol and a solution containing 3-bromoaniline (17.2 mg, 0.100 mmol) in 20 ml absolute ethanol. The reaction mixture was stirred for 4 h under reflux. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 72%; m.p. 398–400 K).

Refinement top

H atoms were located in a difference Fourier map and then were treated using riding models, with C—H = 0.93 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C or O).

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: WinGX (Farrugia, 1999) and 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) and PLATON (Spek, 2009).

Figures top
Fig. 1. The title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

Fig. 2. A view of the crystal packing of the title compound.
(E)-1-[(3-Bromophenyl)iminomethyl]naphthalen-2-ol top
Crystal data top
C17H12BrNOF(000) = 1312
Mr = 326.19Dx = 1.567 Mg m−3
Monoclinic, C2/cMelting point = 398–400 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 31.3965 (19) ÅCell parameters from 14469 reflections
b = 4.8657 (2) Åθ = 1.4–26°
c = 19.0124 (11) ŵ = 2.97 mm−1
β = 107.772 (4)°T = 296 K
V = 2765.8 (3) Å3Needle, yellow
Z = 80.80 × 0.36 × 0.13 mm
Data collection top
Stoe IPDS 2
diffractometer		2706 independent reflections
Radiation source: fine-focus sealed tube1992 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 26.0°, θmin = 1.4°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		h = −38→38
Tmin = 0.421, Tmax = 0.680k = −6→5
14469 measured reflectionsl = −23→23
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0492P)2 + 3.7545P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2706 reflectionsΔρmax = 0.54 e Å−3
181 parametersΔρmin = −0.46 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0
Crystal data top
C17H12BrNOV = 2765.8 (3) Å3
Mr = 326.19Z = 8
Monoclinic, C2/cMo Kα radiation
a = 31.3965 (19) ŵ = 2.97 mm−1
b = 4.8657 (2) ÅT = 296 K
c = 19.0124 (11) Å0.80 × 0.36 × 0.13 mm
β = 107.772 (4)°
Data collection top
Stoe IPDS 2
diffractometer		2706 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		1992 reflections with I > 2σ(I)
Tmin = 0.421, Tmax = 0.680Rint = 0.047
14469 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.02Δρmax = 0.54 e Å−3
2706 reflectionsΔρmin = −0.46 e Å−3
181 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.051469 (14)0.50605 (11)0.33169 (2)0.0901 (2)
N10.16786 (9)−0.1439 (6)0.51791 (14)0.0553 (7)
O10.22611 (8)−0.3797 (6)0.62422 (15)0.0750 (7)
H1A0.2164−0.28900.58630.112*
C10.11528 (11)0.1582 (7)0.42764 (17)0.0533 (8)
H10.09100.09290.44100.064*
C20.15784 (11)0.0544 (6)0.46103 (16)0.0504 (8)
C30.19318 (12)0.1518 (9)0.4388 (2)0.0642 (9)
H30.22170.08130.46020.077*
C40.18636 (14)0.3517 (9)0.3854 (2)0.0721 (11)
H40.21040.41530.37120.087*
C50.14434 (14)0.4590 (8)0.35266 (19)0.0664 (10)
H50.13970.59520.31680.080*
C60.10943 (12)0.3588 (8)0.37456 (17)0.0573 (8)
C70.13773 (11)−0.2878 (7)0.53452 (16)0.0509 (7)
H70.1079−0.26240.50710.061*
C90.19303 (11)−0.5211 (7)0.63643 (18)0.0583 (8)
C80.14817 (10)−0.4839 (6)0.59306 (16)0.0493 (7)
C100.20366 (13)−0.7094 (8)0.69535 (19)0.0672 (10)
H100.2332−0.73010.72450.081*
C110.17155 (14)−0.8593 (9)0.70984 (19)0.0671 (10)
H110.1796−0.98240.74910.080*
C120.12580 (12)−0.8380 (7)0.66784 (17)0.0569 (8)
C130.11370 (11)−0.6490 (7)0.60843 (16)0.0495 (7)
C140.06822 (12)−0.6362 (9)0.5669 (2)0.0658 (9)
H140.0592−0.51610.52710.079*
C150.03683 (14)−0.7972 (9)0.5839 (2)0.0783 (11)
H150.0070−0.78450.55560.094*
C160.04908 (16)−0.9769 (9)0.6424 (3)0.0837 (12)
H160.0275−1.08400.65370.100*
C170.09253 (16)−0.9979 (8)0.6835 (2)0.0753 (11)
H170.1005−1.12070.72280.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0739 (3)0.0978 (4)0.0872 (3)0.0032 (3)0.0079 (2)0.0291 (3)
N10.0548 (16)0.0576 (17)0.0552 (15)0.0016 (14)0.0192 (12)−0.0048 (13)
O10.0496 (14)0.0885 (19)0.0819 (17)0.0024 (14)0.0128 (12)0.0074 (15)
C10.0540 (18)0.056 (2)0.0533 (17)−0.0079 (16)0.0218 (14)−0.0053 (15)
C20.0569 (18)0.0463 (19)0.0498 (16)−0.0055 (15)0.0191 (14)−0.0095 (13)
C30.055 (2)0.070 (2)0.070 (2)−0.0105 (18)0.0237 (17)−0.0091 (19)
C40.073 (3)0.082 (3)0.072 (2)−0.024 (2)0.038 (2)−0.008 (2)
C50.083 (3)0.066 (2)0.0549 (18)−0.017 (2)0.0270 (18)0.0001 (17)
C60.062 (2)0.062 (2)0.0465 (16)−0.0071 (18)0.0135 (15)−0.0046 (15)
C70.0500 (17)0.0521 (19)0.0489 (16)0.0043 (15)0.0126 (14)−0.0053 (14)
C80.0534 (17)0.0482 (17)0.0456 (15)0.0062 (16)0.0138 (13)−0.0061 (14)
C90.0557 (19)0.059 (2)0.0581 (18)0.0081 (18)0.0138 (15)−0.0089 (16)
C100.063 (2)0.073 (3)0.0559 (19)0.018 (2)0.0042 (17)0.0007 (18)
C110.084 (3)0.063 (2)0.0507 (18)0.017 (2)0.0150 (18)0.0037 (17)
C120.076 (2)0.0477 (19)0.0511 (17)0.0081 (18)0.0257 (16)−0.0027 (15)
C130.0557 (18)0.0456 (17)0.0483 (16)0.0065 (15)0.0175 (14)−0.0060 (14)
C140.061 (2)0.066 (2)0.069 (2)0.003 (2)0.0183 (17)0.0064 (18)
C150.058 (2)0.081 (3)0.096 (3)−0.001 (2)0.025 (2)0.002 (2)
C160.087 (3)0.077 (3)0.099 (3)−0.012 (3)0.046 (3)0.001 (3)
C170.096 (3)0.064 (2)0.073 (2)0.007 (3)0.036 (2)0.009 (2)
Geometric parameters (Å, º) top
Br1—C61.893 (4)C9—C101.406 (5)
N1—C71.291 (4)C9—C81.410 (4)
N1—C21.411 (4)C10—H100.9300
O1—C91.324 (4)C11—C101.339 (6)
O1—H1A0.8200C11—C121.418 (5)
C1—C61.375 (5)C11—H110.9300
C1—C21.388 (4)C12—C171.405 (5)
C1—H10.9300C12—C131.416 (4)
C3—C41.375 (6)C13—C141.406 (5)
C3—C21.386 (5)C13—C81.447 (5)
C3—H30.9300C14—C151.372 (6)
C4—H40.9300C14—H140.9300
C5—C41.378 (6)C15—H150.9300
C5—H50.9300C16—C171.353 (6)
C6—C51.375 (5)C16—C151.373 (6)
C7—C81.426 (4)C16—H160.9300
C7—H70.9300C17—H170.9300
C7—N1—C2123.3 (3)O1—C9—C8121.9 (3)
C9—O1—H1A109.5C10—C9—C8120.1 (3)
C6—C1—C2119.2 (3)C11—C10—C9120.5 (3)
C6—C1—H1120.4C11—C10—H10119.7
C2—C1—H1120.4C9—C10—H10119.7
C3—C2—C1119.0 (3)C10—C11—C12122.8 (3)
C3—C2—N1117.1 (3)C10—C11—H11118.6
C1—C2—N1123.9 (3)C12—C11—H11118.6
C4—C3—C2120.6 (4)C17—C12—C13119.5 (3)
C4—C3—H3119.7C17—C12—C11122.1 (3)
C2—C3—H3119.7C13—C12—C11118.4 (3)
C3—C4—C5120.9 (4)C14—C13—C12117.1 (3)
C3—C4—H4119.6C14—C13—C8123.8 (3)
C5—C4—H4119.6C12—C13—C8119.1 (3)
C6—C5—C4118.1 (4)C15—C14—C13121.5 (4)
C6—C5—H5121.0C15—C14—H14119.3
C4—C5—H5121.0C13—C14—H14119.3
C1—C6—C5122.3 (3)C14—C15—C16120.7 (4)
C1—C6—Br1118.7 (3)C14—C15—H15119.7
C5—C6—Br1119.1 (3)C16—C15—H15119.7
N1—C7—C8122.9 (3)C17—C16—C15119.9 (4)
N1—C7—H7118.6C17—C16—H16120.0
C8—C7—H7118.6C15—C16—H16120.0
C9—C8—C7119.5 (3)C16—C17—C12121.3 (4)
C9—C8—C13119.1 (3)C16—C17—H17119.3
C7—C8—C13121.4 (3)C12—C17—H17119.3
O1—C9—C10118.0 (3)
C2—N1—C7—C8−178.8 (3)C4—C3—C2—N1−177.9 (3)
C10—C11—C12—C17179.6 (4)C6—C1—C2—C3−1.3 (5)
C10—C11—C12—C13−0.4 (5)C6—C1—C2—N1177.6 (3)
C17—C12—C13—C14−1.1 (5)C7—N1—C2—C3−166.9 (3)
C11—C12—C13—C14178.8 (3)C7—N1—C2—C114.2 (5)
C17—C12—C13—C8179.6 (3)C1—C6—C5—C40.3 (5)
C11—C12—C13—C8−0.4 (4)Br1—C6—C5—C4179.0 (3)
O1—C9—C8—C7−0.4 (5)C12—C11—C10—C9−0.1 (6)
C10—C9—C8—C7178.6 (3)O1—C9—C10—C11−179.5 (3)
O1—C9—C8—C13178.8 (3)C8—C9—C10—C111.5 (5)
C10—C9—C8—C13−2.2 (5)C12—C13—C14—C150.9 (5)
N1—C7—C8—C91.5 (5)C8—C13—C14—C15−179.9 (3)
N1—C7—C8—C13−177.7 (3)C2—C3—C4—C5−0.2 (6)
C14—C13—C8—C9−177.5 (3)C6—C5—C4—C3−0.5 (6)
C12—C13—C8—C91.7 (4)C13—C14—C15—C16−0.1 (6)
C14—C13—C8—C71.7 (5)C17—C16—C15—C14−0.5 (7)
C12—C13—C8—C7−179.1 (3)C15—C16—C17—C120.3 (6)
C2—C1—C6—C50.7 (5)C13—C12—C17—C160.6 (6)
C2—C1—C6—Br1−178.1 (2)C11—C12—C17—C16−179.4 (4)
C4—C3—C2—C11.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.822.548 (4)147

Experimental details

Crystal data
Chemical formulaC17H12BrNO
Mr326.19
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)31.3965 (19), 4.8657 (2), 19.0124 (11)
β (°) 107.772 (4)
V (Å3)2765.8 (3)
Z8
Radiation typeMo Kα
µ (mm−1)2.97
Crystal size (mm)0.80 × 0.36 × 0.13
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.421, 0.680
No. of measured, independent and
observed [I > 2σ(I)] reflections		14469, 2706, 1992
Rint0.047
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.117, 1.02
No. of reflections2706
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.54, −0.46

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), WinGX (Farrugia, 1999) and SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.822.548 (4)147
 

Acknowledgements

The authors thank the Ondokuz Mayis University Research Fund for financial support of this project.

References

First citationCostamagna, J., Vargas, J., Latorre, R., Alvarado, A. & Mena, G. (1992). Coord. Chem. Rev. 119, 67–88.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationGarnovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69.  CrossRef Web of Science Google Scholar
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ISSN: 2056-9890
Volume 68| Part 9| September 2012| Page o2779
doi:10.1107/S1600536812034824
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