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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 69| Part 7| July 2013| Page o1190
https://doi.org/10.1107/S1600536813017558

2,4-Di­bromo-6-{[(5-chloro-2-methyl­phen­yl)imino]­meth­yl}phenol

Yunfa Zhenga*

aDepartment of Chemistry, Lishui University, Lishui 323000, People's Republic of China
*Correspondence e-mail: zhyunfa@163.com

(Received 23 June 2013; accepted 26 June 2013; online 29 June 2013)

In the mol­ecular structure of the title Schiff base, C14H10Br2ClNO, the chloro­phenyl ring and di­bromo­phenol ring are almost coplanar; the dihedral angle between the planes of the two rings is 10.50 (18)°. There is an intra­molecular O—H⋯N hydrogen bond, with an O⋯N distance of 2.576 (4)Å. The crystal structure is stabilized by π–π stacking of neighbouring aromatic rings along the b-axis direction [centroid–centroid distance = 3.6896 (5) Å].

Related literature

For general background, see: Siddiqui et al. (2006[Siddiqui, H. L., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206-211.]); Fukuda et al. (2009[Fukuda, H., Amimoto, K., Koyama, H. & Kawato, T. (2009). Tetrahedron Lett. 50, 5376-5378.]); Elmali & Elerman (1998[Elmali, A. & Elerman, Y. (1998). J. Mol. Struct. 442, 31-37.]); Karakas et al. (2004[Karakas, A., Elmali, A., Ünverc, H. & Svoboda, I. (2004). J. Mol. Struct. 702, 103-110.]); Ebrahimipour et al. (2012[Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.]). For the similar Schiff base structures, see: Zhou et al. (2009[Zhou, J.-C., Li, N.-X., Zhang, C.-M. & Zhang, Z.-Y. (2009). Acta Cryst. E65, o1949.]); Atalay et al. (2008[Atalay, Ş., Erdem, T. K., Erşahin, F. & Tınkılıç, N. (2008). Acta Cryst. E64, o92.]).

[Scheme 1]

Experimental

Crystal data

  • C14H10Br2ClNO

  • Mr = 403.48

  • Monoclinic, C 2/c

  • a = 31.603 (5) Å

  • b = 6.1828 (10) Å

  • c = 14.890 (2) Å

  • β = 102.594 (15)°

  • V = 2839.4 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 5.89 mm−1

  • T = 295 K

  • 0.38 × 0.35 × 0.30 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.123, Tmax = 0.171

  • 5369 measured reflections

  • 2600 independent reflections

  • 1839 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.082

  • S = 1.00

  • 2600 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.85 2.576 (4) 147

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsn, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsn, USA.]); data reduction: SAINT; program(s) used to solve structure: 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813017558/rk2407sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017558/rk2407Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017558/rk2407Isup3.cml

checkCIF report


Comment top

The Schiff bases derived from salicylaldehyde and methylaniline with various alkyl or halogen substituents have demonstrated potential application in pharmacal field, which have being tested for their antitumor, antimicrobial and antiviral activities (Siddiqui et al., 2006). Schiff base compounds were also studied with respect to photochromic fluorescence materials (Fukuda et al., 2009; Elmali et al., 1998) and photochromic nonlinear optical materials (Karakas et al., 2004). Moreover, Schiff bases have significant importance in the development of Schiff base metal complexes, because Schiff base ligands are potentially capable of forming stable complexes by coordination of metal ions with their oxygen and nitrogen donors (Ebrahimipour et al., 2012). As an extension work on the structural characterization of Schiff base compounds, the title compound is reported.

The molecule of title compound adopts an E configuration, with a C6–N1═C8–C9 torsion angle of 178.4 (3)°. The bond distance of N1═C8 at 1.266 (4)Å is typical of a double bond, which is comparable to those found in similar structures (1.275 (4)Å, Zhou et al., 2009; 1.264 (10)Å, Atalay et al., 2008). The average bond lengths of C–Br at 1.890 (4)Å is longer than that of C–Cl at 1.744 (4)Å due to the radius of Br atom is bigger than that of Cl atom. It is noteworthy to note that H1 atom bonded to O1 is involved in O1–H1···N1 intramolecular hydrogen bond, which resulted in formation of six-membered ring (O1–H1···N1═C8–C9-C10) (Fig. 1). The dibromophenol ring is almost coplanar with the chlorophenyl ring with the dihedral angle between the two planes is 10.50 (18)°. Furthermore, the aromatic ring in the molecule is nearly parallel to the aromatic ring of its neighboring molecule with a ring-to-ring distance of 3.4715 (5)Å (3.6896 (5)Å) and an off-centre angle of 21.98°, indicating a weak π···π stacking interaction between the aromatic rings (Fig. 2). The packing diagram of the title compound shown stacks are arranged in a centrosymmetric manner and a C2 axis passing through the middle point of ac plane (Fig. 3).

Related literature top

For general background, see: Siddiqui et al. (2006); Fukuda et al. (2009); Elmali et al. (1998); Karakas et al. (2004); Ebrahimipour et al. (2012). For the similar Schiff base structures, see: Zhou et al. (2009); Atalay et al. (2008).

Experimental top

A mixture of 5-chloro-2-methylaniline (1.42 g, 10 mmol), 3,5-dibromo-2-hydroxybenzaldehyde (2.80 g, 10 mmol) in 50 ml CH2Cl2 was refluxed under an Ar atmosphere for about 6 h to yield a yellow precipitate. The product was collected by filtration and washed with cold ethanol to give Schiff base compoud in 92.2% yield (3.55 g). The yellow single crystals suitable for X-ray analysis were grown from CH2Cl2 / absolute ethanol (3 / 2) systems by slow evaporation of the solvents at room temperature over a period of about one week.

Refinement top

Hydrogen atoms for the carbon atoms were placed in geometrically idealized positions and constrained to ride on their parent with C–H = 0.96Å and 0.93Å for methyl and aryl type H-atoms, respectively, and refined in a riding mode with Uiso(H) = 1.2Ueq(C) for aromatic H and Uiso(H) = 1.5Ueq(C) for methyl H.

Structure description top

The Schiff bases derived from salicylaldehyde and methylaniline with various alkyl or halogen substituents have demonstrated potential application in pharmacal field, which have being tested for their antitumor, antimicrobial and antiviral activities (Siddiqui et al., 2006). Schiff base compounds were also studied with respect to photochromic fluorescence materials (Fukuda et al., 2009; Elmali et al., 1998) and photochromic nonlinear optical materials (Karakas et al., 2004). Moreover, Schiff bases have significant importance in the development of Schiff base metal complexes, because Schiff base ligands are potentially capable of forming stable complexes by coordination of metal ions with their oxygen and nitrogen donors (Ebrahimipour et al., 2012). As an extension work on the structural characterization of Schiff base compounds, the title compound is reported.

The molecule of title compound adopts an E configuration, with a C6–N1═C8–C9 torsion angle of 178.4 (3)°. The bond distance of N1═C8 at 1.266 (4)Å is typical of a double bond, which is comparable to those found in similar structures (1.275 (4)Å, Zhou et al., 2009; 1.264 (10)Å, Atalay et al., 2008). The average bond lengths of C–Br at 1.890 (4)Å is longer than that of C–Cl at 1.744 (4)Å due to the radius of Br atom is bigger than that of Cl atom. It is noteworthy to note that H1 atom bonded to O1 is involved in O1–H1···N1 intramolecular hydrogen bond, which resulted in formation of six-membered ring (O1–H1···N1═C8–C9-C10) (Fig. 1). The dibromophenol ring is almost coplanar with the chlorophenyl ring with the dihedral angle between the two planes is 10.50 (18)°. Furthermore, the aromatic ring in the molecule is nearly parallel to the aromatic ring of its neighboring molecule with a ring-to-ring distance of 3.4715 (5)Å (3.6896 (5)Å) and an off-centre angle of 21.98°, indicating a weak π···π stacking interaction between the aromatic rings (Fig. 2). The packing diagram of the title compound shown stacks are arranged in a centrosymmetric manner and a C2 axis passing through the middle point of ac plane (Fig. 3).

For general background, see: Siddiqui et al. (2006); Fukuda et al. (2009); Elmali et al. (1998); Karakas et al. (2004); Ebrahimipour et al. (2012). For the similar Schiff base structures, see: Zhou et al. (2009); Atalay et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Dashed line indicates intramolecular hydrogen bond.
[Figure 2] Fig. 2. The π···π stacking of the title compound along the b axis.
[Figure 3] Fig. 3. A packing diagram of the title compound, viewed along the b axis, showing the centrosymmetric arrangement.
2,4-Dibromo-6-{[(5-chloro-2-methylphenyl)imino]methyl}phenol top
Crystal data top
C14H10Br2ClNOF(000) = 1568
Mr = 403.48Dx = 1.888 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1332 reflections
a = 31.603 (5) Åθ = 3.2–29.4°
b = 6.1828 (10) ŵ = 5.89 mm−1
c = 14.890 (2) ÅT = 295 K
β = 102.594 (15)°Block, yellow
V = 2839.4 (8) Å30.38 × 0.35 × 0.30 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		2600 independent reflections
Radiation source: fine-focus sealed tube1839 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ– and ω–scansθmax = 25.4°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −38→37
Tmin = 0.123, Tmax = 0.171k = −7→7
5369 measured reflectionsl = −12→17
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.033P)2]
where P = (Fo2 + 2Fc2)/3
2600 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C14H10Br2ClNOV = 2839.4 (8) Å3
Mr = 403.48Z = 8
Monoclinic, C2/cMo Kα radiation
a = 31.603 (5) ŵ = 5.89 mm−1
b = 6.1828 (10) ÅT = 295 K
c = 14.890 (2) Å0.38 × 0.35 × 0.30 mm
β = 102.594 (15)°
Data collection top
Bruker APEXII CCD
diffractometer		2600 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		1839 reflections with I > 2σ(I)
Tmin = 0.123, Tmax = 0.171Rint = 0.035
5369 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.00Δρmax = 0.41 e Å−3
2600 reflectionsΔρmin = −0.37 e Å−3
174 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br10.032809 (16)0.04959 (8)0.15977 (4)0.07156 (19)
Br20.214268 (14)0.15664 (7)0.23337 (3)0.06296 (18)
Cl10.04381 (4)1.43342 (19)−0.16015 (9)0.0733 (4)
O10.18961 (8)0.5562 (4)0.1191 (2)0.0543 (7)
H10.18270.65660.08290.081*
N10.13813 (10)0.8234 (4)0.0161 (2)0.0398 (7)
C10.09405 (12)1.1128 (6)−0.0732 (3)0.0425 (9)
H1A0.06871.0563−0.06050.051*
C20.09307 (13)1.2987 (6)−0.1244 (3)0.0446 (10)
C30.12950 (15)1.3817 (7)−0.1455 (3)0.0525 (11)
H30.12811.5071−0.18050.063*
C40.16871 (14)1.2770 (6)−0.1143 (3)0.0511 (11)
H40.19361.3326−0.12930.061*
C50.17164 (12)1.0909 (6)−0.0610 (3)0.0417 (9)
C60.13395 (12)1.0104 (6)−0.0405 (2)0.0371 (9)
C70.21455 (13)0.9824 (7)−0.0262 (3)0.0567 (11)
H7A0.22270.99650.03950.085*
H7B0.23611.0493−0.05350.085*
H7C0.21220.8319−0.04240.085*
C80.10618 (13)0.7192 (6)0.0326 (3)0.0416 (9)
H80.07820.76780.00790.050*
C90.11218 (12)0.5254 (5)0.0891 (2)0.0373 (9)
C100.15431 (12)0.4507 (6)0.1287 (2)0.0381 (9)
C110.15814 (12)0.2580 (6)0.1790 (2)0.0391 (9)
C120.12263 (13)0.1421 (6)0.1892 (2)0.0433 (10)
H120.12600.01370.22250.052*
C130.08149 (12)0.2177 (6)0.1493 (3)0.0426 (9)
C140.07621 (12)0.4088 (6)0.1011 (3)0.0435 (10)
H140.04850.46030.07640.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0586 (3)0.0699 (3)0.0919 (4)−0.0168 (2)0.0287 (3)0.0172 (3)
Br20.0527 (3)0.0652 (3)0.0679 (3)0.0080 (2)0.0066 (2)0.0210 (2)
Cl10.0641 (8)0.0718 (8)0.0766 (9)0.0211 (6)−0.0010 (6)0.0219 (6)
O10.0407 (16)0.0495 (17)0.070 (2)−0.0082 (13)0.0062 (14)0.0174 (14)
N10.0429 (19)0.0362 (17)0.0400 (19)−0.0028 (15)0.0082 (15)0.0012 (15)
C10.040 (2)0.039 (2)0.047 (2)−0.0042 (18)0.0064 (19)0.0021 (19)
C20.048 (2)0.043 (2)0.039 (2)0.0113 (19)0.0019 (19)0.0023 (19)
C30.070 (3)0.043 (2)0.043 (3)0.001 (2)0.010 (2)0.0080 (19)
C40.055 (3)0.055 (3)0.046 (3)−0.009 (2)0.017 (2)0.005 (2)
C50.047 (2)0.041 (2)0.037 (2)−0.0023 (18)0.0093 (19)0.0002 (18)
C60.045 (2)0.031 (2)0.035 (2)−0.0017 (17)0.0076 (18)−0.0045 (16)
C70.044 (2)0.071 (3)0.056 (3)−0.002 (2)0.013 (2)0.013 (2)
C80.038 (2)0.037 (2)0.050 (2)0.0060 (18)0.0096 (19)0.0013 (18)
C90.042 (2)0.034 (2)0.038 (2)−0.0011 (17)0.0124 (18)−0.0015 (17)
C100.044 (2)0.034 (2)0.038 (2)−0.0053 (18)0.0106 (18)−0.0038 (17)
C110.043 (2)0.037 (2)0.037 (2)0.0001 (17)0.0105 (18)0.0001 (18)
C120.061 (3)0.035 (2)0.038 (2)0.0003 (19)0.019 (2)0.0013 (17)
C130.042 (2)0.045 (2)0.042 (2)−0.0095 (19)0.0130 (19)−0.0016 (19)
C140.040 (2)0.043 (2)0.050 (2)0.0046 (18)0.0132 (19)0.0041 (19)
Geometric parameters (Å, º) top
Br1—C131.891 (4)C5—C61.385 (5)
Br2—C111.889 (4)C5—C71.500 (5)
Cl1—C21.744 (4)C7—H7A0.9600
O1—C101.327 (4)C7—H7B0.9600
O1—H10.8200C7—H7C0.9600
N1—C81.266 (4)C8—C91.453 (5)
N1—C61.420 (4)C8—H80.9300
C1—C21.376 (5)C9—C141.390 (5)
C1—C61.400 (5)C9—C101.411 (5)
C1—H1A0.9300C10—C111.398 (5)
C2—C31.358 (6)C11—C121.367 (5)
C3—C41.385 (6)C12—C131.387 (5)
C3—H30.9300C12—H120.9300
C4—C51.389 (5)C13—C141.373 (5)
C4—H40.9300C14—H140.9300
C10—O1—H1109.5H7A—C7—H7C109.5
C8—N1—C6123.7 (3)H7B—C7—H7C109.5
C2—C1—C6118.7 (4)N1—C8—C9121.5 (3)
C2—C1—H1A120.7N1—C8—H8119.2
C6—C1—H1A120.7C9—C8—H8119.2
C3—C2—C1121.8 (4)C14—C9—C10120.0 (3)
C3—C2—Cl1119.6 (3)C14—C9—C8119.7 (3)
C1—C2—Cl1118.6 (3)C10—C9—C8120.3 (3)
C2—C3—C4119.1 (4)O1—C10—C11120.0 (3)
C2—C3—H3120.4O1—C10—C9122.2 (3)
C4—C3—H3120.4C11—C10—C9117.8 (3)
C3—C4—C5121.5 (4)C12—C11—C10121.9 (3)
C3—C4—H4119.3C12—C11—Br2119.7 (3)
C5—C4—H4119.3C10—C11—Br2118.4 (3)
C6—C5—C4118.0 (3)C11—C12—C13119.4 (3)
C6—C5—C7121.3 (3)C11—C12—H12120.3
C4—C5—C7120.7 (4)C13—C12—H12120.3
C5—C6—C1120.9 (3)C14—C13—C12120.6 (3)
C5—C6—N1116.8 (3)C14—C13—Br1120.5 (3)
C1—C6—N1122.3 (3)C12—C13—Br1118.9 (3)
C5—C7—H7A109.5C13—C14—C9120.3 (3)
C5—C7—H7B109.5C13—C14—H14119.9
H7A—C7—H7B109.5C9—C14—H14119.9
C5—C7—H7C109.5
C9—C8—N1—C6178.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.852.576 (4)147

Experimental details

Crystal data
Chemical formulaC14H10Br2ClNO
Mr403.48
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)31.603 (5), 6.1828 (10), 14.890 (2)
β (°) 102.594 (15)
V (Å3)2839.4 (8)
Z8
Radiation typeMo Kα
µ (mm−1)5.89
Crystal size (mm)0.38 × 0.35 × 0.30
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.123, 0.171
No. of measured, independent and
observed [I > 2σ(I)] reflections		5369, 2600, 1839
Rint0.035
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.082, 1.00
No. of reflections2600
No. of parameters174
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.37

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.852.576 (4)146.9
 

Acknowledgements

The author acknowledge Lishui University for financial support.

References

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ISSN: 2056-9890
Volume 69| Part 7| July 2013| Page o1190
https://doi.org/10.1107/S1600536813017558
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