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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 64| Part 7| July 2008| Page o1333
doi:10.1107/S1600536808017443

2-Bromo-4-chloro-6-(4-fluoro­phenyl­imino­meth­yl)phenol

G. Puthilibai,a* S. Vasudhevanb and G. Rajagopalc

aDepartment of Chemistry, Bharath University, Chennai 600 073, India, bDepartment of Chemistry, KV Central Leather Research Institute, Chennai 600 020, India, and cDepartment of Chemistry, Government Arts College (Men), Nandanam, Chennai 600 035, India
*Correspondence e-mail: vgputhili@yahoo.com

(Received 14 May 2008; accepted 10 June 2008; online 25 June 2008)

The two mol­ecules of the title compound, C13H8BrClFNO, in the asymmetric unit are inter­connected by π–π inter­actions between the salicylaldehyde and aniline units, the shortest inter­planar distance being 3.317 (3) Å. These pairs and their translation equivalents are further linked by C—H⋯F hydrogen bonds, forming a one-dimensional infinite chain. In addition, there is an intra­molecular O—H⋯N hydrogen bond connecting the OH group and the imine N atom.

Related literature

For related literature, see: Collinson & Fenton (1996[Collinson, S. R. & Fenton, D. E. (1996). Coord. Chem. 148, 19-40.]); Garnovski & Vasil Chenko (2002[Garnovski, A. D. & Vasil Chenko, I. S. (2002). Russ. Chem. Rev. 71, 943-968.]); Kannan & Ramesh (2006[Kannan, S. & Ramesh, R. (2006). Polyhedron, 25, 3095-3103.]); Karvembu et al. (2003[Karvembu, R., Hemalatha, S., Prabhakaran, R. & Natarajan, K. (2003). Inorg. Chem. Commun. 6, 486-490.]); Kumar & Ramesh (2004[Kumar, K. N. & Ramesh, R. (2004). Spectrochim. Acta Part A, 60, 2913-2918.]); Nakajima et al. (1998[Nakajima, K., Ando, Y., Mano, H. & Kojima, M. (1998). Inorg. Chim. Acta, 274, 184-191.]); Prabhakaran et al. (2004[Prabhakaran, R., Geetha, A., Thilagavathi, M., Karvembu, R., Krishnan, V., Bertagnolli, H. & Natarajan, K. (2004). J. Inorg. Biochem. 98, 2131-2140.]); Ramesh & Maheswaran (2003[Ramesh, R. & Maheswaran, S. (2003). J. Inorg. Biochem. 96, 457-462.]); Sivagamasundari & Ramesh (2007[Sivagamasundari, M. & Ramesh, R. (2007). Spectrochim. Acta Part A, 67, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • C13H8BrClFNO

  • Mr = 328.56

  • Triclinic, [P \overline 1]

  • a = 8.2274 (3) Å

  • b = 8.6566 (3) Å

  • c = 10.8880 (4) Å

  • α = 69.545 (2)°

  • β = 70.820 (2)°

  • γ = 62.341 (2)°

  • V = 630.48 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.47 mm−1

  • T = 293 (2) K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Bruker APEX2 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.451, Tmax = 0.573 (expected range = 0.393–0.500)

  • 16111 measured reflections

  • 3975 independent reflections

  • 2533 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.138

  • S = 0.99

  • 3975 reflections

  • 164 parameters

  • H-atom parameters constrained

  • Δρmax = 0.72 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11⋯F1i 0.93 2.45 3.349 (4) 162
O1—H1⋯N1 0.82 1.86 2.577 (3) 146
Symmetry code: (i) x+1, y-1, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017443/im2067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017443/im2067Isup2.hkl

checkCIF report


Comment top

Monobasic bidentate Schiff base ligands exemplified by the title compound exhibiting both N and O donor sites play an important role in the synthesis of metal complexes and represent an important class of chelating ligands (Sivagamasundari et al., 2007; Prabhakaran et al., 2004). Among the prodigious number and variety of Schiff bases, salicylaldimines have been studied widely because of their synthetic proclivity and structural diversity (Collinson et al., 1996; Garnovski et al., 2002). In recent years, there has been considerable interest in the chemistry of transition metal complexes of Schiff bases. This is due to the fact that Schiff bases offer opportunities for inducing substrate chirality, tuning metal centered electronic properties, enhancing solubility and stability of either homogeneous or heterogeneous catalysts and producing antibacterial agents (Karvembu et al., 2003; Nakajima et al., 1998; Kumar et al., 2004; Ramesh et al., 2003; Kannan et al., 2006). With the above view, in our ongoing research, we have chosen the title compound as a specific and representative ligand to synthesize ruthenium complexes. The title compound and its complexes will be screened against the bacterei E. coli, S.aureous, P.mirabilis and P.vulgaris.

The title compound, C9H8BrClFNO, crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. Figure 1 shows the ORTEP representation of the molecule with thermal ellipsoids at the 50% probability level. The packing of the molecules in the unit cell showing the inter molecular interactions is depicted in Figure 2. The molecule and its inversion analogue are linked to each other by Π-Π interactions between the salicylaldehyde moiety and the aniline moiety with the shortest interplanar distance of 3.317 (3) Å (1 - x, 1 - y, 1 - z). The molecules are further connected by C11—H11···F1 hydrogen bonds (2.452 Å, 161.89°, 1 + x, -1 + y, 1 + z) forming an one- dimensional infinite chain. The packing is further stabilized by Van der Waals interactions. In addition, an intramolecular hydrogen bonding O1—H1···N1 (2.577 (3) Å, 145.9°) linking the OH group of the former salicyleldehyde and the imine N atom. The dihedral angle between the salicylaldehyde and aniline moieties is 8.8 (2)°.

Related literature top

For related literature, see: Collinson & Fenton (1996); Garnovski & Vasil Chenko (2002); Kannan & Ramesh (2006); Karvembu et al. (2003); Kumar & Ramesh (2004); Nakajima et al. (1998); Prabhakaran et al. (2004); Ramesh & Maheswaran (2003); Sivagamasundari & Ramesh (2007).

Experimental top

The monobasic bidentate Schiff base ligand, 2-bromo-4-chloro-6-[(4' -fluorophenylimino)-methyl]-phenol, was synthesized by the condensation of 3-bromo-5-chloro-2-hydroxybenzaldehyde (0.1 mmol) with 4-fluoroaniline (0.1 mmol) in a 1:1 molar ratio in MeOH (25 cm3). The solution was heated under reflux for 3 h with continuous stirring and then concentrated to 5 cm3. On cooling the pale orange crystalline product precipitated, was filtered off, washed with ice cold EtOH and dried. The product was recrystallized from EtOH. The purity of the compound was checked by TLC.

Refinement top

All the H atoms were located from the difference Fourier map. However, the aromatic H atoms were geometrically constrained at idealized positions (C—H = 0.93 Å) and were refined using a riding model with Uiso equal to 1.2 times Ueq of the parent carbon atom. The hydroxyl hydrogen was refined isotropically with restraint: O—H = 0.820 (1) Å.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The ORTEP representation of the molecule with thermal ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Packing of molecules in the unit cell. Intermolecular interactions are shown with dashed lines.
2-Bromo-4-chloro-6-(4-fluorophenyliminomethyl)phenol top
Crystal data top
C13H8BrClFNOZ = 2
Mr = 328.56F(000) = 324
Triclinic, P1Dx = 1.731 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2274 (3) ÅCell parameters from 5635 reflections
b = 8.6566 (3) Åθ = 2.7–31.1°
c = 10.8880 (4) ŵ = 3.47 mm−1
α = 69.545 (2)°T = 293 K
β = 70.820 (2)°Rectangle, pale orange
γ = 62.341 (2)°0.30 × 0.20 × 0.20 mm
V = 630.48 (4) Å3
Data collection top
Bruker APEX2 CCD
diffractometer		3975 independent reflections
Radiation source: fine-focus sealed tube2533 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scansθmax = 30.9°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		h = −11→11
Tmin = 0.451, Tmax = 0.573k = −12→12
16111 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0708P)2 + 0.3467P]
where P = (Fo2 + 2Fc2)/3
3975 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.72 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C13H8BrClFNOγ = 62.341 (2)°
Mr = 328.56V = 630.48 (4) Å3
Triclinic, P1Z = 2
a = 8.2274 (3) ÅMo Kα radiation
b = 8.6566 (3) ŵ = 3.47 mm−1
c = 10.8880 (4) ÅT = 293 K
α = 69.545 (2)°0.30 × 0.20 × 0.20 mm
β = 70.820 (2)°
Data collection top
Bruker APEX2 CCD
diffractometer		3975 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		2533 reflections with I > 2σ(I)
Tmin = 0.451, Tmax = 0.573Rint = 0.027
16111 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 0.99Δρmax = 0.72 e Å−3
3975 reflectionsΔρmin = −0.56 e Å−3
164 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
C10.3576 (4)0.9290 (4)0.1434 (3)0.0520 (7)
C20.3513 (4)1.0070 (4)0.2347 (3)0.0572 (7)
H20.27891.12840.23080.069*
C30.4551 (4)0.9013 (4)0.3333 (3)0.0501 (6)
H30.45230.95210.39680.060*
C40.5627 (3)0.7212 (3)0.3389 (2)0.0384 (5)
C50.5679 (4)0.6469 (4)0.2429 (3)0.0486 (6)
H50.64120.52610.24480.058*
C60.4637 (4)0.7527 (4)0.1440 (3)0.0535 (7)
H60.46620.70400.07920.064*
C70.7801 (4)0.4644 (3)0.4552 (3)0.0405 (5)
H70.81170.40860.38660.049*
C80.8715 (3)0.3665 (3)0.5699 (2)0.0366 (5)
C90.8321 (3)0.4496 (3)0.6718 (3)0.0378 (5)
C100.9237 (4)0.3494 (3)0.7792 (3)0.0417 (5)
C111.0468 (4)0.1735 (3)0.7878 (3)0.0433 (6)
H111.10530.10860.86070.052*
C121.0820 (4)0.0950 (3)0.6861 (3)0.0434 (6)
C130.9977 (4)0.1888 (3)0.5779 (3)0.0427 (5)
H131.02480.13380.50980.051*
N10.6581 (3)0.6243 (3)0.4471 (2)0.0402 (5)
O10.7120 (3)0.6194 (2)0.6688 (2)0.0525 (5)
H10.65700.65710.60700.087 (13)*
F10.2529 (3)1.0312 (3)0.04826 (19)0.0759 (6)
Cl11.23745 (13)−0.12851 (9)0.69813 (9)0.0681 (2)
Br10.87756 (6)0.45988 (5)0.91496 (4)0.07867 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0463 (14)0.0613 (17)0.0414 (14)−0.0219 (13)−0.0227 (12)0.0098 (13)
C20.0576 (17)0.0432 (14)0.0585 (18)−0.0087 (13)−0.0269 (14)0.0004 (13)
C30.0554 (16)0.0432 (14)0.0507 (15)−0.0129 (12)−0.0241 (12)−0.0063 (12)
C40.0385 (12)0.0400 (12)0.0367 (12)−0.0169 (10)−0.0153 (10)0.0002 (10)
C50.0505 (15)0.0456 (14)0.0504 (15)−0.0129 (12)−0.0236 (12)−0.0079 (12)
C60.0586 (17)0.0672 (19)0.0400 (14)−0.0264 (15)−0.0212 (12)−0.0057 (13)
C70.0443 (13)0.0398 (12)0.0407 (12)−0.0146 (10)−0.0174 (10)−0.0078 (10)
C80.0373 (11)0.0352 (11)0.0377 (12)−0.0126 (9)−0.0156 (9)−0.0040 (9)
C90.0362 (11)0.0339 (11)0.0425 (13)−0.0089 (9)−0.0154 (10)−0.0080 (10)
C100.0437 (13)0.0425 (13)0.0413 (13)−0.0127 (10)−0.0174 (10)−0.0102 (10)
C110.0449 (13)0.0397 (12)0.0425 (13)−0.0128 (10)−0.0222 (11)0.0005 (11)
C120.0429 (13)0.0310 (11)0.0522 (15)−0.0083 (10)−0.0200 (11)−0.0044 (10)
C130.0471 (13)0.0347 (12)0.0462 (14)−0.0100 (10)−0.0177 (11)−0.0102 (10)
N10.0409 (11)0.0395 (11)0.0407 (11)−0.0139 (9)−0.0183 (9)−0.0034 (9)
O10.0568 (11)0.0372 (9)0.0584 (12)0.0023 (8)−0.0302 (9)−0.0173 (8)
F10.0744 (12)0.0842 (14)0.0574 (11)−0.0237 (11)−0.0444 (10)0.0151 (10)
Cl10.0768 (5)0.0338 (3)0.0812 (6)0.0009 (3)−0.0358 (4)−0.0126 (3)
Br10.0981 (3)0.0702 (3)0.0663 (3)−0.00208 (19)−0.0451 (2)−0.03146 (18)
Geometric parameters (Å, º) top
C1—F11.355 (3)C7—H70.9300
C1—C61.361 (5)C8—C131.391 (3)
C1—C21.360 (5)C8—C91.399 (3)
C2—C31.382 (4)C9—O11.334 (3)
C2—H20.9300C9—C101.396 (3)
C3—C41.381 (4)C10—C111.373 (4)
C3—H30.9300C10—Br11.878 (3)
C4—C51.387 (4)C11—C121.379 (4)
C4—N11.418 (3)C11—H110.9300
C5—C61.386 (4)C12—C131.370 (3)
C5—H50.9300C12—Cl11.741 (3)
C6—H60.9300C13—H130.9300
C7—N11.270 (3)O1—H10.8200
C7—C81.460 (3)
F1—C1—C6118.6 (3)C13—C8—C9120.0 (2)
F1—C1—C2118.5 (3)C13—C8—C7119.4 (2)
C6—C1—C2122.8 (2)C9—C8—C7120.5 (2)
C1—C2—C3118.3 (3)O1—C9—C10119.7 (2)
C1—C2—H2120.9O1—C9—C8122.2 (2)
C3—C2—H2120.9C10—C9—C8118.1 (2)
C4—C3—C2120.9 (3)C11—C10—C9122.0 (2)
C4—C3—H3119.6C11—C10—Br1119.22 (18)
C2—C3—H3119.6C9—C10—Br1118.82 (19)
C3—C4—C5119.2 (2)C10—C11—C12118.6 (2)
C3—C4—N1116.1 (2)C10—C11—H11120.7
C5—C4—N1124.7 (2)C12—C11—H11120.7
C6—C5—C4120.0 (3)C13—C12—C11121.5 (2)
C6—C5—H5120.0C13—C12—Cl1120.1 (2)
C4—C5—H5120.0C11—C12—Cl1118.38 (19)
C1—C6—C5118.8 (3)C12—C13—C8119.8 (2)
C1—C6—H6120.6C12—C13—H13120.1
C5—C6—H6120.6C8—C13—H13120.1
N1—C7—C8121.3 (2)C7—N1—C4122.7 (2)
N1—C7—H7119.3C9—O1—H1109.5
C8—C7—H7119.3
F1—C1—C2—C3178.5 (3)O1—C9—C10—C11179.2 (3)
C6—C1—C2—C3−1.0 (5)C8—C9—C10—C11−1.1 (4)
C1—C2—C3—C40.1 (5)O1—C9—C10—Br1−1.2 (3)
C2—C3—C4—C50.8 (4)C8—C9—C10—Br1178.50 (19)
C2—C3—C4—N1−177.8 (3)C9—C10—C11—C120.8 (4)
C3—C4—C5—C6−0.9 (4)Br1—C10—C11—C12−178.8 (2)
N1—C4—C5—C6177.6 (2)C10—C11—C12—C130.3 (4)
F1—C1—C6—C5−178.6 (3)C10—C11—C12—Cl1−179.7 (2)
C2—C1—C6—C51.0 (5)C11—C12—C13—C8−0.9 (4)
C4—C5—C6—C10.0 (4)Cl1—C12—C13—C8179.0 (2)
N1—C7—C8—C13177.0 (3)C9—C8—C13—C120.6 (4)
N1—C7—C8—C9−2.6 (4)C7—C8—C13—C12−179.0 (2)
C13—C8—C9—O1−179.9 (2)C8—C7—N1—C4−178.1 (2)
C7—C8—C9—O1−0.3 (4)C3—C4—N1—C7−170.8 (3)
C13—C8—C9—C100.4 (4)C5—C4—N1—C710.7 (4)
C7—C8—C9—C10180.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···F1i0.932.453.349 (4)162
O1—H1···N10.821.862.577 (3)146
Symmetry code: (i) x+1, y−1, z+1.

Experimental details

Crystal data
Chemical formulaC13H8BrClFNO
Mr328.56
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.2274 (3), 8.6566 (3), 10.8880 (4)
α, β, γ (°)69.545 (2), 70.820 (2), 62.341 (2)
V (Å3)630.48 (4)
Z2
Radiation typeMo Kα
µ (mm−1)3.47
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker APEX2 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.451, 0.573
No. of measured, independent and
observed [I > 2σ(I)] reflections		16111, 3975, 2533
Rint0.027
(sin θ/λ)max (Å−1)0.723
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.138, 0.99
No. of reflections3975
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.72, −0.56

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···F1i0.932.453.349 (4)162
O1—H1···N10.821.862.577 (3)145.9
Symmetry code: (i) x+1, y−1, z+1.
 

Acknowledgements

The authors thank the Sophisticated Analytical Instruments Facility, Indian Institute of Technology Madras, Chennai, for the X-ray data collection.

References

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ISSN: 2056-9890
Volume 64| Part 7| July 2008| Page o1333
doi:10.1107/S1600536808017443
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