Crystal structure of 3-{(E)-[(3,4-di­chloro­phen­yl)imino]­meth­yl}benzene-1,2-diol

Muhammad Nawaz Tahir; Hazoor Ahmad Shad; Abdul Rauf; Abdul Haleem Khan

doi:10.1107/S2056989015001401

. 2015 Jan 28;71(Pt 2):o137–o138. doi: 10.1107/S2056989015001401

Crystal structure of 3-{(E)-[(3,4-dichlorophenyl)imino]methyl}benzene-1,2-diol

Muhammad Nawaz Tahir ^a,^*, Hazoor Ahmad Shad ^b, Abdul Rauf ^c, Abdul Haleem Khan ^d

PMCID: PMC4384559 PMID: 25878871

Abstract

In the title Schiff base, C₁₃H₉Cl₂NO₂, which arose from the condensation of 3,4-dichloroaniline with 2,3-dihydroxybenzaldehyde, the dihedral angle between the aromatic rings is 44.74 (13)°. Intramolecular O—H⋯O and O—H⋯N hydrogen bonds close S(5) and S(6) rings, respectively. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R ₂ ²(10) loops. A weak C—H⋯π interaction is also observed.

Keywords: crystal structure; benzene-1,2-diol; Schiff base; hydrogen bonding

Related literature

For related structures, see: Fun et al. (2011 ▸); Keleşoğlu et al. (2009 ▸); Shuja et al. (2006 ▸); Tahir et al. (2012 ▸); Temel et al. (2007 ▸). graphic file with name e-71-0o137-scheme1.jpg

Experimental

Crystal data

C₁₃H₉Cl₂NO₂
M _r = 282.11
Triclinic,
a = 6.4237 (8) Å
b = 8.8412 (11) Å
c = 11.7799 (15) Å
α = 88.606 (6)°
β = 76.588 (6)°
γ = 70.193 (5)°
V = 611.20 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 296 K
0.34 × 0.26 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T _min = 0.844, T _max = 0.902
8896 measured reflections
2671 independent reflections
1866 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.164
S = 1.04
2671 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015001401/hb7353sup1.cif

e-71-0o137-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001401/hb7353Isup2.hkl

e-71-0o137-Isup2.hkl^{(146.8KB, hkl)}

Click here for additional data file.^{(4.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015001401/hb7353Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015001401/hb7353fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.^{(1.1MB, tif)}

PLATON . DOI: 10.1107/S2056989015001401/hb7353fig2.tif

The partial packing (PLATON; Spek, 2009), which shows that molecules form dimers due to O—H⋯O interactions.

CCDC reference: 1044861

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg1 is the centroid of the benzene ring (C1C6).

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.89	2.608(3)	146
O2H2O1	0.82	2.28	2.729(3)	115
O2H2O1ⁱ	0.82	2.20	2.846(3)	136
C12H12Cg1ⁱⁱ	0.93	2.83	3.538(4)	134

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr. Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

S1. Comment

The title compound (I), (Fig. 1) has been synthesized for forming different metal complexes.

The crystal structures of 2-[(E)-(2,4,6-trichlorophenyl)iminomethyl] phenol (Fun et al., 2011), (E)-3-((2-fluorophenylimino)methyl) benzene-1,2-diol (Temel et al., 2007), (E)-3-[(3-bromophenyl) iminomethyl]benzene-1,2-diol (Kelesoglu et al., 2009), 4-([(E)-2, 3-dihydroxybenzylidene]amino)-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide (Tahir et al., 2012) and 3-(4-bromophenyliminomethyl)benzene-1,2-diol (Shuja et al., 2006) have been published which are related to the title compound due to two moieties of the Schiff base.

In (I) the moieties of 2,3-dihydroxybenzaldehyde A (C1–C7/O1/O2) and 3,4-dichloroanilline B (C8—13/N1/CL1/CL2) are almost planar with r.m.s. deviation of 0.0225 and 0.0172 Å, respectively. The dihedral angle between A/B is 44.219 (50)°. In (I), S(5) and S(6) ring motifs are present due to H-bondings of O—H···O and O—H···N types (Table 1, Fig. 2). The molecules are dimerized due to bifercated H-bonding of O—H···O type (Table 1, Fig. 2). There exist C—H···π (Table 1) and π···π interactions to stablize the dimmers. A π···π interactions between Cg1···Cg1ⁱ [i = -x, 2 - y, 1 - z] at a distance of 3.9101 (15) Å, where Cg1 is centroid of benzene ring (C1—C6) exists. Similarly, there is π···π interactions between Cg2···Cg2ⁱⁱ [il = 1 - x, 1 - y, - z] at a distance of 4.1194 (17) Å, where Cg2 is centroid of benzene ring (C8—C13).

S2. Experimental

Equimolar quantities of 3,4-dichloroanilline and 2,3-dihydroxybenzaldehyde were refluxed in methanol for 2 h. The resulting mixture was evaporated to grow crystals. Red prisms were obtained after 48 h.