2,4-Diiodo-6-{[4-(morpholin-4-yl)phenyl]iminomethyl}phenol

K Manvizhi; G Chakkaravarthi; G Anbalagan; G Rajagopal

doi:10.1107/S1600536811034519

. 2011 Aug 27;67(Pt 9):o2500. doi: 10.1107/S1600536811034519

2,4-Diiodo-6-{[4-(morpholin-4-yl)phenyl]iminomethyl}phenol

K Manvizhi ^a, G Chakkaravarthi ^b,^*, G Anbalagan ^c, G Rajagopal ^d,^*

PMCID: PMC3200745 PMID: 22064908

Abstract

In the title compound, C₁₇H₁₆I₂N₂O₂, the two aromatic rings are almost coplanar [dihedral angle 2.57 (15)°]. The morpholine ring adopts a chair conformation. The molecular structure is stabilized by an O—H⋯N hydrogen bond and the crystal packing exhibits weak intermolecular C—H⋯O and π–π [centroid-to-centroid distances 3.663 (3)-4.073 (3) Å] interactions.

Related literature

For the biological activity of morpholine derivatives, see: Lan et al. (2010 ▶); Raparti et al.(2009 ▶). For a related structure, see: Yang et al. (2011 ▶). For the definition of puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₁₆I₂N₂O₂
M _r = 534.12
Monoclinic,
a = 26.4133 (16) Å
b = 7.6598 (4) Å
c = 18.0332 (11) Å
β = 91.417 (2)°
V = 3647.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 3.46 mm⁻¹
T = 295 K
0.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.467, T _max = 0.545
17839 measured reflections
7647 independent reflections
4855 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.113
S = 1.16
7647 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 1.22 e Å⁻³
Δρ_min = −1.72 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034519/bt5621sup1.cif

e-67-o2500-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034519/bt5621Isup2.hkl

e-67-o2500-Isup2.hkl^{(366.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034519/bt5621Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.82	2.548 (5)	146
C6—H6⋯O1ⁱ	0.93	2.50	3.413 (5)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

Comment

Morpholine derivatives possess anticancer and antimicrobial (Lan et al., 2010; Raparti et al., 2009) activities. In the title compound, (I) (Fig. 1), The bond lengths C═N [1.282 (6)Å], C—I [C1—I1 = 2.092 (4) and C5—I2 = 2.097 (4) Å] are comparable with the literature values and the bond lengths of the morpholine ring are agree well with a reported related structure (Yang et al., 2011).

The mean planes of two benzene rings (C8–C13) and (C1–C6) are oriented at an angle of 2.57 (15)°. The morpholine ring adopts a chair conformation [Puckering parameters are Q = 0.544 (6)Å, θ = 170.8 (5)° and φ = 180 (4)° (Cremer & Pople, 1975) for the ring (O1/C15/C14/N2/C17/C16)].

The molecular structure is stabilized by O—H···N hydrogen bonding and the crystal packing exhibit weak intermolecular C—H···O (Fig. 2 and Table 1) and π–π [Cg2···Cg3(-x, -y, -z) distance of 3.663 (3)Å; Cg2···Cg3(-x, 1 - y, -z) distance of 4.074 (3)Å] interactions.

Experimental

An ethanolic solution (20 ml) of 4-(4-aminophenyl)morpholine (10 mmol) was magnetically stirred in a round bottom flask followed by drop wise addition of ethanolic solution of 3,5-diiodosalicylaldehyde (10 mmol). The reaction mixture was then refluxed for 3 h and upon cooling to 273 K, a red crystalline solid precipitates from the mixture. The solid which is separated out was filtered washed with ice cold ethanol and dried in vaccuo over anhydrous CaCl₂. Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature. m.p. 443 K.