2-(Benzotriazol-1-ylmethyl­amino)­benzoic acid

Yao Wang; Mai-Hua Yin; Guo-Fang Zhang

doi:10.1107/S160053680800740X

. 2008 Mar 20;64(Pt 4):o735. doi: 10.1107/S160053680800740X

2-(Benzotriazol-1-ylmethylamino)benzoic acid

Yao Wang ^a, Mai-Hua Yin ^a, Guo-Fang Zhang ^a,^*

PMCID: PMC2960979 PMID: 21202125

Abstract

The title compound, C₁₄H₁₂N₄O₂, a new N,O,N′-tridentate ligand, is V-shaped with the mean plane through the benzotriazole system [planar to within 0.013 (2) Å] inclined by 67.7 (1)° to the mean plane through the benzene ring. In the molecule there is an intramolecular N—H⋯O hydrogen bond involving the amine H atom and the carbonyl O atom. In the crystal structure, symmtry-related molecules are connected by intermolecular O—H⋯N and C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For related literature, see: Trofimenko (1993 ▶); Zhang, Dou et al. (2007 ▶); Zhang et al. (2006 ▶); Zhang, Zhou et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₂N₄O₂
M _r = 268.28
Monoclinic,
a = 10.225 (6) Å
b = 15.669 (8) Å
c = 8.098 (4) Å
β = 97.671 (7)°
V = 1285.8 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 (2) K
0.19 × 0.16 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.982, T _max = 0.993
9692 measured reflections
2388 independent reflections
1438 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.117
S = 1.02
2388 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (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, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800740X/su2045sup1.cif

e-64-0o735-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800740X/su2045Isup2.hkl

e-64-0o735-Isup2.hkl^{(117.4KB, hkl)}

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
N4—H4D⋯O1	0.86 (2)	1.99 (3)	2.691 (3)	138 (2)
O2—H2⋯N3ⁱ	0.82	1.95	2.746 (3)	165
C7—H7A⋯O1ⁱⁱ	0.97	2.40	3.214 (3)	141
C12—H12⋯Cg2ⁱⁱⁱ	0.93	2.94	3.836 (3)	163

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg2 is the centroid of the C1–C6 ring.

Acknowledgments

We thank Shaanxi Normal University for research grants.

supplementary crystallographic information

Comment

In last decades, extensive investigations have been undertaken to design and synthesize pyrazole-based tridentate ligands, with the aim of mimiking structures and functions of some metalloenzymes (Trofimenko, 1993). Our interests have been focused on the design and syntheses of flexible N,O,N ligands derived from pyrazoles and triazoles since a certain flexibility might afford coordination versitality of the ligands. We have therefore designed and synthesized a number of such ligands as well as their transition-metal complexes (Zhang, Dou et al., 2007; Zhang, Yin et al., 2006; Zhang, Zhou et al., 2007). Here we report on the structure of a new N,O,N tridentate ligand, 2-(benzotriazolylmethylamino)benzoic acid.

The molecular structure of the title compound is illustrated in Fig. 1. Details of the hydrogen bonding and C—H···\p interactions are given in Table 1. The molecule is V-shaped with the best plane through the benzotriazole moiety (planar to within 0.013 (2) Å) inclined by 67.7 (1)° to the best plane through the benzene ring (C8—C13). In the molecule there is an intra-molecular N—H···O hydrogen bond involving the amine (N4) hydrogen, H4D, and the carbonyl O-atom, O1 (Table 1).

In the crystal structure symmetry related molecules form dimers via C—H···π interactions involving C12—H12 and the benzene ring [(C1—C6 = Cg2ⁱⁱⁱ]. Adjacent molecules are linked by O2—H2···N3ⁱ hydrogen bonds to form zigzag chains parallel to the a axis, and these chains are further linked by C7—H7A···O1ⁱⁱ intermolecular hydrogen bonds (Table 1).

Experimental

The NH hydrogen atom was located from a difference Fourier map and freely refined, N—H = 0.86 (2) Å. The remainder of the H-atoms were included in calculated positions and treated as riding atoms: O—H = 0.82 Å and C—H = 0.93 - 0.97 \%A, with U_iso(H) = 1.5U_eq(O) and 1.2U_eq(C).