[1-(3-Chloro­phen­yl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate

Nübia Boechat; Maria de Lourdes G Ferreira; Monica M Bastos; James L Wardell; Solange M S V Wardell; Edward R T Tiekink

doi:10.1107/S1600536811041560

. 2011 Oct 12;67(Pt 11):o2934–o2935. doi: 10.1107/S1600536811041560

[1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate

Nübia Boechat ^a, Maria de Lourdes G Ferreira ^a, Monica M Bastos ^a, James L Wardell ^b,^‡, Solange M S V Wardell ^c, Edward R T Tiekink ^d,^*

PMCID: PMC3247347 PMID: 22219965

Abstract

The asymmetric unit of the title hydrate, C₉H₈ClN₃O·0.5H₂O, comprises two independent 1,2,3-triazole molecules and a water molecule of crystallization. The dihedral angles between the six- and five-membered rings in the 1,2,3-triazole molecules are 12.71 (19) and 17.3 (2)°. The most significant different between them is found in the relative orientations of the terminal CH₂OH groups with one being close to perpendicular to the five-membered ring [N—C—C—O torsion angle = 82.2 (5)°], while in the other molecule, a notable deviation from a perpendicular disposition is found [torsion angle = −60.3 (5)°]. Supramolecular chains feature in the crystal packing sustained by O—H⋯(O,N) interactions along the a-axis direction. The chains are connected via C—H⋯N interactions and the resultant layers stack along the b axis.

Related literature

For background to the synthesis, biological activity and structures of 1,2,3-triazole derivatives, see: Boechat et al. (2010 ▶, 2011 ▶); Costa et al. (2006a ▶,b ▶); Ferreira et al. (2007 ▶); Jordão et al. (2009 ▶). For the synthesis, see: Boechat et al. (2011 ▶). For additional geometric analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C₉H₈ClN₃O·0.5H₂O
M _r = 218.64
Triclinic,
a = 6.0078 (4) Å
b = 7.4897 (4) Å
c = 22.3145 (15) Å
α = 88.818 (4)°
β = 89.901 (2)°
γ = 80.493 (4)°
V = 990.07 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 120 K
0.18 × 0.18 × 0.02 mm

Data collection

Bruker–Nonius APEX II CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.843, T _max = 1.000
10830 measured reflections
3909 independent reflections
2948 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.163
S = 1.00
3909 reflections
274 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), QMol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041560/hb6439sup1.cif

e-67-o2934-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041560/hb6439Isup2.hkl

e-67-o2934-Isup2.hkl^{(187.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041560/hb6439Isup3.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—H1o⋯O2ⁱ	0.84 (4)	1.82 (4)	2.651 (5)	170 (5)
O2—H2o⋯O1w	0.84 (6)	1.80 (5)	2.641 (5)	174 (7)
O1w—H1w⋯N3	0.84 (4)	2.00 (4)	2.837 (5)	172 (4)
O1w—H2w⋯O1ⁱⁱ	0.84 (4)	1.95 (5)	2.663 (5)	142 (4)
C16—H16⋯O1wⁱⁱⁱ	0.95	2.45	3.383 (5)	166
C7—H7⋯N6^iv	0.95	2.28	3.197 (5)	161

Open in a new tab

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

Acknowledgments

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

supplementary crystallographic information

Comment

Boechat and colleagues have been interested in the synthesis, biological activities and structures of 1,2,3-triazole derivatives for some time (Boechat et al., 2010, 2011; Costa et al., 2006a, 2006b; Ferreira et al., 2007, Jordão et al., 2009). Recently, they reported the synthesis and anti-mycobacterial activities of a number of 4-R-1-(X-phenyl)-triazole derivatives (Boechat et al., 2011). The structure of one of the compounds investigated in that study, i.e. the title compound, (I), is now reported.

Two independent molecules of a 1,2,3-triazole derivative and a water molecule of solvation comprise the asymmetric unit of (I), Fig. 1. Geometrically, the two organic molecules are similar to each other with r.m.s. deviations for bond distances and angles being 0.0092 Å and 0.757°, respectively (Spek, 2009). From the overlay diagram, Fig. 2, it is evident that the independent molecules approximate mirror images. However, small twists between the five- and six-membered rings differ with the dihedral angles between their least-squares being 12.71 (19) and 17.3 (2)°, respectively, for the N1- and N4-containing molecules. More notable are the relative orientations of the terminal CH₂OH groups as seen in the values of the N3—C8—C9—O1 and N6—C17—C18—O2 torsion angles of 82.2 (5) and -60.3 (5)°, respectively.

The presence of a supramolecular chain along the a axis is the most prominent feature of the crystal packing, Fig. 3. These are mediated by O—H···O and O—H···N hydrogen bonds with additional stability afforded by C—H···O interactions, Table 1. Chains are connected into layers via C—H···N interactions, Table 1, and these stack along the b axis. The closest interactions between layers are of the type Cl···Cl, i.e. Cl1···Cl2ⁱ = 3.4117 (15) Å for i: 2 - x, 1 - y, 1 - z.

Experimental

The compound, obtained as published (Boechat et al., 2011), was recrystallized from EtOH as a hemihydrate.