1-Benzyl-1H-benzotriazole 3-oxide monohydrate

P Selvarathy Grace; Samuel Robinson Jebas; B Ravindran Durai Nayagam; Dieter Schollmeyer

doi:10.1107/S1600536812044868

. 2012 Nov 7;68(Pt 12):o3297. doi: 10.1107/S1600536812044868

1-Benzyl-1H-benzotriazole 3-oxide monohydrate

P Selvarathy Grace ^a, Samuel Robinson Jebas ^b, B Ravindran Durai Nayagam ^a,^*, Dieter Schollmeyer ^c

PMCID: PMC3588841 PMID: 23468806

Abstract

In the title hydrate, C₁₃H₁₁N₃O·H₂O, the benzotriazole ring system is planar (r.m.s. deviation = 0.007 Å) and is almost orthogonal to the phenyl ring to which it is linked by a methylene group, forming a dihedral angle of 81.87 (15)°. In the crystal, molecules are linked into chains along [001] by O—H⋯O hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H⋯O, C—H⋯π and π–π [centroid–centroid distance between the five- and six-membered rings of the benzotriazole ring system = 3.595 (3) Å] interactions.

Related literature

For the biological activity of benzotriazole derivatives, see: Kopańska et al. (2005 ▶); Sarala et al. (2007 ▶). For their applications, see: Kopec et al. (2008 ▶); Krawczyk & Gdaniec (2005 ▶); Smith et al. (2001 ▶); Sha et al. (1996 ▶). For a related structure, see: Selvarathy Grace et al. (2012 ▶).

Experimental

Crystal data

C₁₃H₁₁N₃O·H₂O
M _r = 243.26
Orthorhombic,
a = 12.556 (5) Å
b = 20.881 (8) Å
c = 4.6651 (18) Å
V = 1223.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.40 × 0.05 × 0.04 mm

Data collection

Bruker SMART APEXII diffractometer
15911 measured reflections
1677 independent reflections
1118 reflections with I > 2σ(I)
R _int = 0.132

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.140
S = 0.98
1677 reflections
164 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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

Supplementary Material

Click here for additional data file.^{(21.4KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044868/tk5165sup1.cif

e-68-o3297-sup1.cif^{(21.4KB, cif)}

Click here for additional data file.^{(82.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044868/tk5165Isup2.hkl

e-68-o3297-Isup2.hkl^{(82.6KB, hkl)}

Click here for additional data file.^{(4.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812044868/tk5165Isup3.cml

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

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

Cg1 is the centroid of the C11–C16 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1W ⁱ	0.82	1.93	2.744 (3)	169
O1W—H2W⋯O17	0.85	1.95	2.800 (3)	180
C10—H10A⋯O17ⁱⁱ	0.99	2.45	3.400 (5)	161
C10—H10B⋯Cg3ⁱⁱⁱ	0.99	2.51	3.382 (4)	147

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

supplementary crystallographic information

Comment

Benzotriazole derivatives show biological activities such as anti-inflammatory, diuretic, anti-viral and anti-hypertensive (Kopańska et al., 2005; Sarala et al., 2007). They have been used as a corrosion inhibitor, anti-freeze agent, ultraviolet light stabilizer for plastics and as an anti-foggant in photography (Krawczyk & Gdaniec, 2005; Smith et al., 2001). N-aryloxy derivatives of benzotriazole have anti-mycobacterial activity (Kopec et al., 2008). Benzotriazole possessing three vicinal N atoms, is used as an anti-fouling and anti-wear reagent (Sha et al., 1996). Due to the above mentioned applications of benzotriazole, we have systematically synthesised and investigated the structures of novel benzotriazole derivatives. We have already reported the crystal structure of 1-(benzyl)-1H-benzotriazole (Selvarathy Grace et al., 2012). Here, we report the crystal structure of the title compound (I).

The benzotriazole ring in (I), Fig 1, is essentially planar with the maximum deviation from planarity being 0.010 (3) Å for atom N3. The mean plane of the benzotriazole ring (N1–N3,C4–C9) forms a dihedral angle of 81.87 (15) Å with the mean plane of the phenyl ring (C11–C16).

The molecules are linked into a one dimensional chain along [001] by O—H···O hydrogen bonds, Table 1 and Fig. 2. The crystal packing is stabilized by π–π stacking interactions with the centroid-centroid distance of 3.595 (3) Å [symmetry code: x, y, -1+z], together with C—H···O and C—H···π interactions, Table 1.

Experimental

A mixture of sodium salt of 1-hydroxyl benzotriazole (0.157 g, 1 mmol) and benzyl chloride (0.126 g, 1 mmol) in a mixture comprising ethanol, water and sodium ethoxide (10 ml) were heated at 333 K with continuous stirring for 6 h. The mixture was kept aside for slow evaporation. After a week, crystals suitable for X-ray diffraction were obtained.