4-[(E)-({4-[(4-Amino­phen­yl)sulfon­yl]phen­yl}imino)­meth­yl]phenol ethanol monosolvate

Sadaf Afzal; Zareen Akhter; M Nawaz Tahir

doi:10.1107/S1600536812021563

. 2012 May 19;68(Pt 6):o1789. doi: 10.1107/S1600536812021563

4-[(E)-({4-[(4-Aminophenyl)sulfonyl]phenyl}imino)methyl]phenol ethanol monosolvate

Sadaf Afzal ^a, Zareen Akhter ^a, M Nawaz Tahir ^b,^*

PMCID: PMC3379368 PMID: 22719566

Abstract

In the title compound, C₁₉H₁₆N₂O₃S·C₂H₆O, the 4-hydroxybenzylidene group is oriented at dihedral angles of 73.17 (7) and 77.06 (7)° with respect to the aniline groups. The sulfonyl group make dihedral angles of 44.89 (13) and 59.16 (12)° with the adjacent aniline groups. In the crystal, a two-dimensional polymeric network parallel to (010) is formed by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds. There also exist π–π interactions with a distance of 3.5976 (18) Å between the centroids of hydroxyphenyl rings.

Related literature

For related structures, see: Bocelli & Cantoni (1990 ▶). graphic file with name e-68-o1789-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₆N₂O₃S·C₂H₆O
M _r = 398.47
Monoclinic,
a = 8.5281 (3) Å
b = 25.3057 (12) Å
c = 9.4084 (4) Å
β = 96.738 (3)°
V = 2016.40 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.948, T _max = 0.968
16497 measured reflections
3969 independent reflections
2400 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.138
S = 1.04
3969 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021563/bq2358sup1.cif

e-68-o1789-sup1.cif^{(27.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021563/bq2358Isup2.hkl

e-68-o1789-Isup2.hkl^{(190.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021563/bq2358Isup3.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
O1—H1⋯O4ⁱ	0.82	1.89	2.698 (3)	171
N2—H2A⋯O3ⁱⁱ	0.86	2.30	3.105 (3)	156
N2—H2B⋯O2ⁱⁱⁱ	0.86	2.21	3.026 (3)	157
O4—H4⋯N1^iv	0.82	2.13	2.926 (3)	162

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The structure of 4,4'-diamino-diphenylsulfone (Bocelli & Cantoni, 1990), related to the title compound, (I), shown in Fig. 1., has been published previously. In (I), the 4-hydroxybenzaldehyde moiety A (O1/C1–C7), the anilinic moieties of 4,4'-diaminodiphenylsulfone B (N1/C8—C13) and C (C14—C19/N2) are planar with r.m.s. deviation of 0.0125 Å, 0.0320 Å and 0.0151 Å, respectively. The dihedral angles between A/B, A/C and B/C are 73.17 (7)°, 77.06 (7)° and 77.16 (7)°, respectively. The sulfonyl group D (O2/S1/O3) is of course planar. The dihedral angles between B/D and C/D are 59.16 (12)° and 44.89 (13)°, respectively. The molecules are stabilized in the form of two-dimensional polymeric network due to various type of H-bondings (Table 1, Fig. 2). There exist also π–π interaction between the CgA···CgAⁱ [i = 1 - x,-y, 2 - z] at a distance of 3.5976 (18) Å, where CgA is the centroid of phenyl ring (C1—C6).

Experimental

In a 250 ml two-necked round bottomed flask equipped with condenser and magnetic stirrer, 4-hydroxy benzaldehyde (1.22 g, 0.01 mole) was dissolved in 50 ml of dried ethanol under inert atmosphere of nitrogen gas. 4,4'-diaminodiphenylsulfone (1.24 g, 0.005 mole) was added to it. The reaction mixture was refluxed for 6 h with constant stirring, and the progress of the reaction was monitored by TLC [n-hexane/ethanol (3:1)] respectively. The yellow colored product thus obtained was filtered, dried and hence recrystallized in ethanol. Yield: 88%, m.p.: 385 K.