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

Li, J.

doi:10.1107/S1600536810052542

organic compounds

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Volume 67| Part 1| January 2011| Page o199

https://doi.org/10.1107/S1600536810052542

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

Jian Li ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ljwfu@163.com

(Received 6 December 2010; accepted 14 December 2010; online 18 December 2010)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.046
wR(F²) = 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

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
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052542/lh5186Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

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

Crystal data top

C₇H₆N₂S·C₉H₁₀O₅	F(000) = 728
M_r = 348.37	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1736 reflections
a = 10.2737 (10) Å	θ = 2.3–22.2°
b = 10.4325 (11) Å	µ = 0.23 mm⁻¹
c = 15.0308 (17) Å	T = 298 K
β = 93.646 (1)°	Block, light yellow
V = 1607.7 (3) Å³	0.44 × 0.42 × 0.35 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2849 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→12
T_min = 0.905, T_max = 0.924	k = −12→11
7888 measured reflections	l = −17→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0403P)² + 0.9023P] where P = (F_o² + 2F_c²)/3
2849 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₇H₆N₂S·C₉H₁₀O₅	V = 1607.7 (3) Å³
M_r = 348.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2737 (10) Å	µ = 0.23 mm⁻¹
b = 10.4325 (11) Å	T = 298 K
c = 15.0308 (17) Å	0.44 × 0.42 × 0.35 mm
β = 93.646 (1)°

Data collection top

Bruker SMART CCD diffractometer	2849 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1679 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.924	R_int = 0.044
7888 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
2849 reflections	Δρ_min = −0.28 e Å⁻³
218 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.4153 (2)	0.6895 (2)	0.77925 (16)	0.0453 (7)
N2	0.5207 (3)	0.5250 (3)	0.85991 (17)	0.0582 (8)
H2A	0.5263	0.5700	0.9079	0.070*
H2B	0.5514	0.4483	0.8601	0.070*
O1	0.3673 (2)	0.2580 (2)	0.52228 (13)	0.0535 (6)
O2	0.3477 (3)	0.1157 (3)	0.41181 (16)	0.0818 (9)
O3	0.0688 (2)	0.1771 (2)	0.49890 (13)	0.0617 (7)
O4	0.0927 (2)	0.3513 (2)	0.58303 (13)	0.0582 (6)
H4	0.0728	0.3016	0.6222	0.087*
O5	0.0846 (2)	0.2395 (2)	0.30892 (13)	0.0513 (6)
S1	0.45412 (9)	0.48354 (8)	0.68714 (6)	0.0561 (3)
C1	0.3281 (3)	0.2196 (3)	0.4405 (2)	0.0465 (8)
C2	0.0935 (3)	0.2904 (3)	0.5075 (2)	0.0420 (8)
C3	0.2594 (3)	0.3276 (3)	0.39140 (18)	0.0389 (7)
H3	0.3188	0.4010	0.3896	0.047*
C4	0.1297 (3)	0.3720 (3)	0.43033 (18)	0.0393 (7)
H4A	0.1347	0.4625	0.4476	0.047*
C5	0.0336 (3)	0.3534 (3)	0.3470 (2)	0.0471 (8)
H5	−0.0588	0.3494	0.3594	0.057*
C6	0.0675 (3)	0.4538 (3)	0.2804 (2)	0.0525 (9)
H6	0.0209	0.5280	0.2656	0.063*
C7	0.1755 (3)	0.4154 (3)	0.2479 (2)	0.0510 (9)
H7	0.2214	0.4562	0.2046	0.061*
C8	0.2104 (3)	0.2917 (3)	0.29452 (19)	0.0477 (8)
H8	0.2683	0.2352	0.2631	0.057*
C9	0.4275 (4)	0.1628 (3)	0.5812 (2)	0.0713 (11)
H9A	0.3621	0.1046	0.5998	0.107*
H9B	0.4689	0.2043	0.6325	0.107*
H9C	0.4915	0.1162	0.5504	0.107*
C10	0.4647 (3)	0.5736 (3)	0.7857 (2)	0.0460 (8)
C11	0.3640 (3)	0.7130 (3)	0.6929 (2)	0.0446 (8)
C12	0.3787 (3)	0.6131 (3)	0.6332 (2)	0.0470 (8)
C13	0.3350 (3)	0.6251 (4)	0.5446 (2)	0.0638 (10)
H13	0.3454	0.5582	0.5048	0.077*
C14	0.2767 (4)	0.7362 (4)	0.5167 (2)	0.0722 (12)
H14	0.2479	0.7453	0.4571	0.087*
C15	0.2594 (3)	0.8357 (4)	0.5750 (2)	0.0652 (10)
H15	0.2179	0.9102	0.5544	0.078*
C16	0.3029 (3)	0.8262 (3)	0.6639 (2)	0.0547 (9)
H16	0.2917	0.8936	0.7032	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0546 (16)	0.0395 (17)	0.0419 (16)	0.0030 (13)	0.0026 (13)	−0.0020 (12)
N2	0.085 (2)	0.0442 (18)	0.0454 (17)	0.0167 (16)	0.0036 (15)	−0.0005 (14)
O1	0.0663 (15)	0.0479 (15)	0.0437 (13)	0.0040 (11)	−0.0162 (11)	−0.0004 (11)
O2	0.122 (2)	0.0556 (17)	0.0649 (17)	0.0284 (16)	−0.0192 (15)	−0.0140 (14)
O3	0.0928 (18)	0.0521 (16)	0.0407 (13)	−0.0243 (14)	0.0078 (12)	−0.0001 (11)
O4	0.0928 (18)	0.0474 (14)	0.0354 (13)	−0.0022 (13)	0.0114 (12)	−0.0016 (11)
O5	0.0674 (15)	0.0475 (14)	0.0376 (12)	−0.0173 (12)	−0.0078 (11)	0.0021 (11)
S1	0.0723 (6)	0.0454 (6)	0.0512 (5)	−0.0042 (5)	0.0095 (4)	−0.0105 (4)
C1	0.049 (2)	0.049 (2)	0.0406 (19)	−0.0010 (17)	−0.0008 (15)	0.0009 (17)
C2	0.0448 (18)	0.045 (2)	0.0358 (19)	−0.0019 (16)	0.0019 (14)	0.0015 (16)
C3	0.0438 (18)	0.0360 (18)	0.0364 (17)	−0.0060 (14)	−0.0007 (14)	−0.0001 (14)
C4	0.0461 (18)	0.0365 (18)	0.0349 (16)	−0.0033 (15)	−0.0011 (14)	−0.0007 (14)
C5	0.0470 (19)	0.051 (2)	0.0426 (19)	−0.0059 (16)	−0.0058 (15)	0.0068 (17)
C6	0.060 (2)	0.051 (2)	0.0444 (19)	−0.0001 (18)	−0.0153 (17)	0.0096 (17)
C7	0.068 (2)	0.050 (2)	0.0335 (18)	−0.0141 (19)	−0.0058 (17)	0.0080 (16)
C8	0.061 (2)	0.049 (2)	0.0333 (17)	−0.0028 (17)	0.0037 (15)	0.0004 (15)
C9	0.085 (3)	0.065 (3)	0.060 (2)	0.011 (2)	−0.021 (2)	0.015 (2)
C10	0.0497 (19)	0.044 (2)	0.0450 (19)	−0.0030 (16)	0.0108 (15)	−0.0010 (16)
C11	0.0409 (18)	0.047 (2)	0.0455 (19)	−0.0080 (16)	0.0020 (15)	0.0001 (16)
C12	0.0486 (19)	0.052 (2)	0.0399 (19)	−0.0135 (16)	0.0028 (15)	−0.0056 (16)
C13	0.069 (2)	0.071 (3)	0.051 (2)	−0.018 (2)	−0.0037 (19)	−0.014 (2)
C14	0.071 (3)	0.093 (3)	0.050 (2)	−0.018 (2)	−0.0163 (19)	0.005 (2)
C15	0.056 (2)	0.073 (3)	0.065 (3)	−0.007 (2)	−0.0136 (19)	0.013 (2)
C16	0.054 (2)	0.053 (2)	0.056 (2)	−0.0020 (18)	−0.0012 (17)	0.0009 (18)

Geometric parameters (Å, º) top

N1—C10	1.312 (4)	C4—H4A	0.9800
N1—C11	1.391 (4)	C5—C6	1.504 (4)
N2—C10	1.323 (4)	C5—H5	0.9800
N2—H2A	0.8600	C6—C7	1.304 (4)
N2—H2B	0.8600	C6—H6	0.9300
O1—C1	1.330 (3)	C7—C8	1.501 (4)
O1—C9	1.443 (3)	C7—H7	0.9300
O2—C1	1.188 (4)	C8—H8	0.9800
O3—C2	1.214 (4)	C9—H9A	0.9600
O4—C2	1.302 (3)	C9—H9B	0.9600
O4—H4	0.8200	C9—H9C	0.9600
O5—C8	1.432 (4)	C11—C12	1.390 (4)
O5—C5	1.432 (4)	C11—C16	1.395 (4)
S1—C12	1.733 (3)	C12—C13	1.384 (4)
S1—C10	1.752 (3)	C13—C14	1.359 (5)
C1—C3	1.499 (4)	C13—H13	0.9300
C2—C4	1.504 (4)	C14—C15	1.377 (5)
C3—C8	1.556 (4)	C14—H14	0.9300
C3—C4	1.560 (4)	C15—C16	1.385 (4)
C3—H3	0.9800	C15—H15	0.9300
C4—C5	1.557 (4)	C16—H16	0.9300

C10—N1—C11	110.7 (3)	C6—C7—H7	127.1
C10—N2—H2A	120.0	C8—C7—H7	127.1
C10—N2—H2B	120.0	O5—C8—C7	101.9 (3)
H2A—N2—H2B	120.0	O5—C8—C3	101.0 (2)
C1—O1—C9	116.9 (3)	C7—C8—C3	106.5 (3)
C2—O4—H4	109.5	O5—C8—H8	115.2
C8—O5—C5	95.9 (2)	C7—C8—H8	115.2
C12—S1—C10	88.80 (16)	C3—C8—H8	115.2
O2—C1—O1	124.2 (3)	O1—C9—H9A	109.5
O2—C1—C3	126.3 (3)	O1—C9—H9B	109.5
O1—C1—C3	109.5 (3)	H9A—C9—H9B	109.5
O3—C2—O4	123.7 (3)	O1—C9—H9C	109.5
O3—C2—C4	121.9 (3)	H9A—C9—H9C	109.5
O4—C2—C4	114.3 (3)	H9B—C9—H9C	109.5
C1—C3—C8	113.2 (3)	N1—C10—N2	124.2 (3)
C1—C3—C4	115.1 (2)	N1—C10—S1	115.4 (2)
C8—C3—C4	100.9 (2)	N2—C10—S1	120.5 (3)
C1—C3—H3	109.1	C12—C11—N1	114.8 (3)
C8—C3—H3	109.1	C12—C11—C16	119.9 (3)
C4—C3—H3	109.1	N1—C11—C16	125.3 (3)
C2—C4—C5	112.0 (2)	C13—C12—C11	120.8 (3)
C2—C4—C3	112.4 (2)	C13—C12—S1	128.9 (3)
C5—C4—C3	100.0 (2)	C11—C12—S1	110.3 (2)
C2—C4—H4A	110.7	C14—C13—C12	118.9 (4)
C5—C4—H4A	110.7	C14—C13—H13	120.5
C3—C4—H4A	110.7	C12—C13—H13	120.5
O5—C5—C6	101.9 (3)	C13—C14—C15	121.2 (3)
O5—C5—C4	101.3 (2)	C13—C14—H14	119.4
C6—C5—C4	106.6 (2)	C15—C14—H14	119.4
O5—C5—H5	115.1	C14—C15—C16	120.9 (4)
C6—C5—H5	115.1	C14—C15—H15	119.5
C4—C5—H5	115.1	C16—C15—H15	119.5
C7—C6—C5	105.9 (3)	C15—C16—C11	118.2 (3)
C7—C6—H6	127.0	C15—C16—H16	120.9
C5—C6—H6	127.0	C11—C16—H16	120.9
C6—C7—C8	105.8 (3)

C9—O1—C1—O2	−5.4 (5)	C6—C7—C8—O5	32.5 (3)
C9—O1—C1—C3	175.8 (3)	C6—C7—C8—C3	−73.0 (3)
O2—C1—C3—C8	1.0 (5)	C1—C3—C8—O5	87.8 (3)
O1—C1—C3—C8	179.7 (2)	C4—C3—C8—O5	−35.8 (3)
O2—C1—C3—C4	116.3 (4)	C1—C3—C8—C7	−166.1 (3)
O1—C1—C3—C4	−64.9 (3)	C4—C3—C8—C7	70.3 (3)
O3—C2—C4—C5	48.4 (4)	C11—N1—C10—N2	179.8 (3)
O4—C2—C4—C5	−132.4 (3)	C11—N1—C10—S1	0.4 (3)
O3—C2—C4—C3	−63.3 (4)	C12—S1—C10—N1	0.6 (2)
O4—C2—C4—C3	115.9 (3)	C12—S1—C10—N2	−178.8 (3)
C1—C3—C4—C2	−3.9 (3)	C10—N1—C11—C12	−1.6 (4)
C8—C3—C4—C2	118.4 (3)	C10—N1—C11—C16	179.2 (3)
C1—C3—C4—C5	−122.8 (3)	N1—C11—C12—C13	−178.4 (3)
C8—C3—C4—C5	−0.6 (3)	C16—C11—C12—C13	0.9 (5)
C8—O5—C5—C6	49.2 (2)	N1—C11—C12—S1	2.1 (3)
C8—O5—C5—C4	−60.7 (2)	C16—C11—C12—S1	−178.7 (2)
C2—C4—C5—O5	−82.4 (3)	C10—S1—C12—C13	179.0 (3)
C3—C4—C5—O5	36.8 (3)	C10—S1—C12—C11	−1.5 (2)
C2—C4—C5—C6	171.4 (3)	C11—C12—C13—C14	−0.3 (5)
C3—C4—C5—C6	−69.4 (3)	S1—C12—C13—C14	179.2 (3)
O5—C5—C6—C7	−31.4 (3)	C12—C13—C14—C15	−0.7 (6)
C4—C5—C6—C7	74.3 (3)	C13—C14—C15—C16	1.0 (6)
C5—C6—C7—C8	−0.6 (3)	C14—C15—C16—C11	−0.4 (5)
C5—O5—C8—C7	−49.7 (3)	C12—C11—C16—C15	−0.5 (5)
C5—O5—C8—C3	60.0 (2)	N1—C11—C16—C15	178.6 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₇H₆N₂S·C₉H₁₀O₅
M_r	348.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.2737 (10), 10.4325 (11), 15.0308 (17)
β (°)	93.646 (1)
V (Å³)	1607.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.44 × 0.42 × 0.35

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.905, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	7888, 2849, 1679
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 1.03
No. of reflections	2849
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, y−1/2, −z+3/2.

Acknowledgements

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

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Deng, L. P. & Hu, Y. Z. (2007). J. Heterocycl. Chem. 44, 597–601. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y.-Y., Hu, R.-D. & Wang, Y.-J. (2008). Acta Cryst. E64, o1442. Web of Science CSD CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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