Benzothia­zol-2-amine–3-meth­oxy­carbonyl-7-oxabicyclo­[2.2.1]hept-5-ene-2-carb­oxy­lic acid (1/1)

Jian Li

doi:10.1107/S1600536810052542

. 2010 Dec 18;67(Pt 1):o199. doi: 10.1107/S1600536810052542

Benzothiazol-2-amine–3-methoxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1/1)

Jian Li ^a,^*

PMCID: PMC3050333 PMID: 21522700

Abstract

In the title 1:1 adduct, C₇H₆N₂S·C₉H₁₀O₅, all non-H atoms of the benzothiazol-2-amine molecule are essentially coplanar, with a maximum deviation of 0.0286 (9) Å for the S atom. In the crystal, intermolecular N—H⋯O and O—H⋯N hydrogen bonds connect two molecules of each type into centrosymmetric four-component clusters.

Related literature

For applications of 3-(methoxycarbonyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid and its derivatives, see: Deng & Hu (2007 ▶). For a related structure, see: Wang et al. (2008 ▶).

Experimental

Crystal data

C₇H₆N₂S·C₉H₁₀O₅
M _r = 348.37
Monoclinic,
a = 10.2737 (10) Å
b = 10.4325 (11) Å
c = 15.0308 (17) Å
β = 93.646 (1)°
V = 1607.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.44 × 0.42 × 0.35 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.905, T _max = 0.924
7888 measured reflections
2849 independent reflections
1679 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.123
S = 1.03
2849 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052542/lh5186sup1.cif

e-67-0o199-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052542/lh5186Isup2.hkl

e-67-0o199-Isup2.hkl^{(139.9KB, 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
N2—H2A⋯O3ⁱ	0.86	2.08	2.849 (3)	148
N2—H2B⋯O3ⁱⁱ	0.86	2.46	2.987 (4)	120
N2—H2B⋯O5ⁱⁱ	0.86	2.14	2.949 (4)	157
O4—H4⋯N1ⁱⁱⁱ	0.82	1.89	2.676 (3)	162

Open in a new tab

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

Acknowledgments

The author thanks Shandong Provincial Natural Science Foundation, China (ZR2009BL027) for support.

supplementary crystallographic information

Comment

7-Oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboxylic anhydride has been widely employed in clinical practice (Deng & Hu, 2007). In this paper, the crystal structure of the title compound is reported. The asymmetric unit consistes of a 3-(methoxycarbonyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid molecule and a benzothiazol-2-amine molecule (Fig. 1). Bond lengths and angles are comparable to those observed for the 1:1 cocrystal of rac-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid and benzothiazol-2-amine (Wang, et al., 2008). In the 3-(methoxycarbonyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid molecule the dihedral angle between the mean plane formed by atoms C3/C4/C5/C8 and the plane fromed by C5/C6/C7/C8 is 69.3 (2) °. All non-hydrogen atoms of the benzothiazol-2-amine molecule are essentially co-planar with a maximum deviation of 0.0286 (9)Å for atom S1. In the crystal structure, intermolecular N—H···O and O—H···N hydrogen bonds connect two molecules of each type into centrosymmetric four component clusters (Fig. 2, Table 1).

Experimental

A mixture of exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboxylic anhydride (0.332 g, 2 mmol) and benzothiazol-2-amine (0.3 g, 2 mmol) in methanol (5 ml) was stirred for 5 h at room temperature. The reacted solution was left for crystallization at room temperature. The single-crystal suitable for X-ray determination was obtained by evaporation after 5 d.