rac-7-Oxabicyclo­[2.2.1]heptane-2,3-dicarboxylic acid–2-amino-1,3,4-thia­diazole–water (1/1/1)

Wang, N.; Lin, Q.-Y.; Wang, Y.-J.

doi:10.1107/S1600536809021825

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1590

doi:10.1107/S1600536809021825

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rac-7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid–2-amino-1,3,4-thiadiazole–water (1/1/1)

Na Wang,^a Qiu-Yue Lin ^a ^* and Yan-Jun Wang ^a

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and, College of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky51@zjnu.cn

(Received 27 May 2009; accepted 9 June 2009; online 17 June 2009)

The title compound, C₈H₁₀O₅·C₂H₃N₃S·H₂O, was synthesized by the reaction of 2-amino-1,3,4-thiadiazole with norcantharidin. The crystal structure is stabilized by N—H⋯O, N—H⋯N, O—H⋯O and O—H⋯N hydrogen bonds. In addition, weak π–π interactions are observed between symmetry-related thiadiazole ring systems [centroid–centroid distance = 3.9110 (3) Å, interplanar spacing = 3.4845 Å].

Related literature

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (norcantharidin) is a lower toxicity anticancer drug, see: Shimi & Zaki (1982 ).

Experimental

Crystal data

C₈H₁₀O₅·C₂H₃N₃S·H₂O
M_r = 305.31
Monoclinic, P 2₁ /n
a = 5.7678 (5) Å
b = 18.4267 (15) Å
c = 12.7546 (11) Å
β = 101.336 (6)°
V = 1329.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.30 × 0.16 × 0.09 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.977
10820 measured reflections
2995 independent reflections
2026 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.133
S = 1.05
2995 reflections
187 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.86	2.11	2.930 (3)	160
N1—H1C⋯N3ⁱⁱ	0.86	2.15	2.994 (3)	166
N1—H1C⋯N2ⁱⁱ	0.86	2.69	3.519 (3)	161
O2—H2A⋯O1Wⁱⁱⁱ	0.82	1.81	2.626 (2)	176
O5—H5B⋯N2^iv	0.82	1.85	2.664 (2)	172
O1W—H1WA⋯O3^v	0.859 (17)	1.910 (17)	2.766 (2)	175 (3)
O1W—H1WB⋯O4^vi	0.819 (17)	2.51 (3)	3.151 (3)	137 (3)
O1W—H1WB⋯O1^vi	0.819 (17)	2.55 (3)	3.061 (3)	122 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) -x, -y, -z.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021825/at2800sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021825/at2800Isup2.hkl

checkCIF report

Comment top

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (norcantharidin) derived from cantharidin is a lower toxicity anticancer drug (Shimi & Zaki, 1982). The title compound was synthesized by the reaction of 2-amino-1,3,4-thiadiazole with 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (norcantharidin). In this paper, we reports its structure.

X-ray crystallography measurement confirmed the molecular structure and the atom connectivity for the title compound (Fig. 1). The crystal structure is stabilized by N—H···O, N—H···N, O—H···O and O—H···N hydrogen bonds (Table 1). Further, weak π–π interactions are observed between symmetry related thiadiazole ring systems [centroid-centroid distance of 3.9110 (3)Å and interplanar spacing of 3.4845 Å].

Related literature top

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (norcantharidin) is a lower toxicity anticancer drug, see: Shimi & Zaki (1982).

Experimental top

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride and 2-amino-1,3,4-thiadiazole were dissolved in tetrahydrofuran and the mixture was stirred for 6 h at room temperature. The clear solution was left undisturbed for days to give colourless crystals of the compound.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of (I) showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability.

rac-7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid–2-amino-1,3,4-thiadiazole–water (1/1/1) top

Crystal data top

C₈H₁₀O₅·C₂H₃N₃S·H₂O	F(000) = 640
M_r = 305.31	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1905 reflections
a = 5.7678 (5) Å	θ = 2.0–27.6°
b = 18.4267 (15) Å	µ = 0.27 mm⁻¹
c = 12.7546 (11) Å	T = 296 K
β = 101.336 (6)°	Block, colourless
V = 1329.1 (2) Å³	0.30 × 0.16 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	2995 independent reflections
Radiation source: fine-focus sealed tube	2026 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 27.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.949, T_max = 0.977	k = −24→23
10820 measured reflections	l = −16→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) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.062P)² + 0.3174P] where P = (F_o² + 2F_c²)/3
2995 reflections	(Δ/σ)_max = 0.001
187 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₈H₁₀O₅·C₂H₃N₃S·H₂O	V = 1329.1 (2) Å³
M_r = 305.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.7678 (5) Å	µ = 0.27 mm⁻¹
b = 18.4267 (15) Å	T = 296 K
c = 12.7546 (11) Å	0.30 × 0.16 × 0.09 mm
β = 101.336 (6)°

Data collection top

Bruker APEXII area-detector diffractometer	2995 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2026 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.977	R_int = 0.040
10820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	3 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.30 e Å⁻³
2995 reflections	Δρ_min = −0.29 e Å⁻³
187 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
C1	−0.2976 (5)	0.05357 (14)	0.3265 (2)	0.0537 (7)
H1B	−0.3880	0.0947	0.3053	0.064*
C2	−0.0094 (4)	−0.03835 (13)	0.37115 (19)	0.0401 (6)
C3	−0.7049 (4)	−0.14263 (12)	−0.02775 (19)	0.0371 (5)
H3A	−0.7478	−0.1570	−0.1031	0.044*
C4	−0.4729 (4)	−0.10527 (12)	0.11367 (19)	0.0378 (5)
H4A	−0.3228	−0.0881	0.1563	0.045*
C5	−0.5597 (4)	−0.17663 (11)	0.15371 (18)	0.0308 (5)
H5A	−0.6555	−0.1649	0.2069	0.037*
C6	−0.7289 (4)	−0.20482 (11)	0.05131 (18)	0.0320 (5)
H6A	−0.8916	−0.2080	0.0630	0.038*
C7	−0.8388 (4)	−0.07593 (13)	−0.0002 (2)	0.0436 (6)
H7A	−0.9932	−0.0888	0.0135	0.052*
H7B	−0.8573	−0.0399	−0.0566	0.052*
C8	−0.6732 (4)	−0.04919 (12)	0.1016 (2)	0.0451 (6)
H8A	−0.7506	−0.0499	0.1626	0.054*
H8B	−0.6158	−0.0006	0.0925	0.054*
C9	−0.3734 (4)	−0.23059 (12)	0.20304 (18)	0.0339 (5)
C10	−0.6556 (4)	−0.27519 (12)	0.00717 (19)	0.0357 (5)
S1	−0.00230 (12)	0.04890 (3)	0.32282 (6)	0.0514 (2)
N1	0.1766 (3)	−0.08184 (12)	0.39063 (18)	0.0534 (6)
H1A	0.1631	−0.1250	0.4145	0.064*
H1C	0.3110	−0.0670	0.3794	0.064*
N2	−0.2197 (3)	−0.05840 (10)	0.38689 (17)	0.0431 (5)
N3	−0.3854 (4)	−0.00394 (11)	0.36078 (19)	0.0511 (6)
O1	−0.4621 (3)	−0.12182 (8)	0.00484 (13)	0.0399 (4)
O1W	0.3491 (3)	0.19399 (12)	0.19534 (16)	0.0573 (5)
O2	−0.1540 (3)	−0.20904 (9)	0.21051 (15)	0.0470 (5)
H2A	−0.0641	−0.2405	0.2405	0.071*
O3	−0.4251 (3)	−0.28854 (9)	0.23715 (14)	0.0453 (4)
O4	−0.4568 (3)	−0.28772 (9)	−0.00388 (16)	0.0527 (5)
O5	−0.8343 (3)	−0.31955 (9)	−0.02355 (17)	0.0575 (5)
H5B	−0.7870	−0.3568	−0.0474	0.086*
H1WA	0.213 (4)	0.1986 (18)	0.212 (2)	0.086*
H1WB	0.317 (5)	0.2024 (19)	0.1311 (15)	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0577 (16)	0.0398 (14)	0.064 (2)	0.0017 (11)	0.0119 (14)	0.0069 (13)
C2	0.0431 (13)	0.0412 (13)	0.0358 (14)	−0.0098 (10)	0.0075 (10)	−0.0022 (10)
C3	0.0419 (13)	0.0369 (12)	0.0311 (13)	0.0077 (9)	0.0038 (10)	−0.0009 (10)
C4	0.0383 (12)	0.0342 (12)	0.0394 (14)	−0.0035 (9)	0.0041 (10)	0.0000 (10)
C5	0.0310 (11)	0.0334 (11)	0.0289 (12)	0.0019 (8)	0.0081 (9)	0.0004 (9)
C6	0.0280 (11)	0.0316 (11)	0.0371 (14)	0.0013 (8)	0.0081 (9)	−0.0036 (9)
C7	0.0443 (13)	0.0368 (12)	0.0486 (16)	0.0118 (10)	0.0062 (11)	0.0015 (11)
C8	0.0606 (16)	0.0306 (12)	0.0448 (16)	0.0032 (10)	0.0119 (12)	−0.0033 (11)
C9	0.0339 (12)	0.0390 (12)	0.0300 (13)	0.0015 (9)	0.0094 (9)	−0.0002 (10)
C10	0.0366 (13)	0.0334 (12)	0.0365 (14)	0.0016 (9)	0.0058 (10)	−0.0027 (9)
S1	0.0575 (4)	0.0399 (4)	0.0583 (5)	−0.0095 (3)	0.0150 (3)	0.0073 (3)
N1	0.0475 (12)	0.0419 (12)	0.0697 (17)	−0.0015 (9)	0.0089 (11)	0.0107 (11)
N2	0.0455 (11)	0.0354 (10)	0.0480 (13)	−0.0044 (8)	0.0085 (9)	0.0048 (9)
N3	0.0462 (12)	0.0434 (12)	0.0625 (15)	0.0023 (9)	0.0083 (11)	0.0072 (11)
O1	0.0417 (9)	0.0391 (9)	0.0425 (10)	0.0032 (7)	0.0170 (7)	0.0082 (7)
O1W	0.0381 (10)	0.0837 (14)	0.0524 (12)	−0.0079 (9)	0.0140 (9)	−0.0121 (11)
O2	0.0315 (9)	0.0499 (10)	0.0589 (12)	0.0004 (7)	0.0068 (8)	0.0103 (8)
O3	0.0374 (9)	0.0435 (9)	0.0558 (12)	0.0049 (7)	0.0108 (8)	0.0171 (8)
O4	0.0406 (10)	0.0447 (10)	0.0747 (14)	0.0032 (7)	0.0163 (9)	−0.0214 (9)
O5	0.0411 (10)	0.0362 (9)	0.0954 (16)	−0.0057 (7)	0.0137 (9)	−0.0213 (10)

Geometric parameters (Å, º) top

C1—N3	1.287 (3)	C6—H6A	0.9800
C1—S1	1.715 (3)	C7—C8	1.534 (3)
C1—H1B	0.9300	C7—H7A	0.9700
C2—N2	1.320 (3)	C7—H7B	0.9700
C2—N1	1.323 (3)	C8—H8A	0.9700
C2—S1	1.725 (2)	C8—H8B	0.9700
C3—O1	1.433 (3)	C9—O3	1.212 (3)
C3—C7	1.529 (3)	C9—O2	1.311 (3)
C3—C6	1.550 (3)	C10—O4	1.205 (3)
C3—H3A	0.9800	C10—O5	1.313 (3)
C4—O1	1.434 (3)	N1—H1A	0.8600
C4—C5	1.530 (3)	N1—H1C	0.8600
C4—C8	1.535 (3)	N2—N3	1.381 (3)
C4—H4A	0.9800	O1W—H1WA	0.859 (17)
C5—C9	1.508 (3)	O1W—H1WB	0.819 (17)
C5—C6	1.558 (3)	O2—H2A	0.8200
C5—H5A	0.9800	O5—H5B	0.8200
C6—C10	1.507 (3)

N3—C1—S1	115.3 (2)	C5—C6—H6A	110.7
N3—C1—H1B	122.4	C3—C7—C8	101.18 (17)
S1—C1—H1B	122.4	C3—C7—H7A	111.5
N2—C2—N1	122.5 (2)	C8—C7—H7A	111.5
N2—C2—S1	113.71 (18)	C3—C7—H7B	111.5
N1—C2—S1	123.80 (18)	C8—C7—H7B	111.5
O1—C3—C7	103.14 (18)	H7A—C7—H7B	109.4
O1—C3—C6	102.49 (17)	C7—C8—C4	101.53 (18)
C7—C3—C6	109.34 (19)	C7—C8—H8A	111.5
O1—C3—H3A	113.6	C4—C8—H8A	111.5
C7—C3—H3A	113.6	C7—C8—H8B	111.5
C6—C3—H3A	113.6	C4—C8—H8B	111.5
O1—C4—C5	102.67 (17)	H8A—C8—H8B	109.3
O1—C4—C8	102.77 (18)	O3—C9—O2	122.9 (2)
C5—C4—C8	108.84 (18)	O3—C9—C5	121.68 (19)
O1—C4—H4A	113.8	O2—C9—C5	115.39 (19)
C5—C4—H4A	113.8	O4—C10—O5	123.7 (2)
C8—C4—H4A	113.8	O4—C10—C6	123.5 (2)
C9—C5—C4	116.94 (17)	O5—C10—C6	112.67 (18)
C9—C5—C6	114.05 (17)	C1—S1—C2	86.76 (12)
C4—C5—C6	101.48 (17)	C2—N1—H1A	120.0
C9—C5—H5A	108.0	C2—N1—H1C	120.0
C4—C5—H5A	108.0	H1A—N1—H1C	120.0
C6—C5—H5A	108.0	C2—N2—N3	111.89 (19)
C10—C6—C3	108.99 (18)	C1—N3—N2	112.4 (2)
C10—C6—C5	115.12 (17)	C3—O1—C4	96.42 (15)
C3—C6—C5	100.22 (17)	H1WA—O1W—H1WB	101 (2)
C10—C6—H6A	110.7	C9—O2—H2A	109.5
C3—C6—H6A	110.7	C10—O5—H5B	109.5

O1—C4—C5—C9	90.1 (2)	C6—C5—C9—O3	−62.0 (3)
C8—C4—C5—C9	−161.49 (19)	C4—C5—C9—O2	2.8 (3)
O1—C4—C5—C6	−34.65 (19)	C6—C5—C9—O2	120.9 (2)
C8—C4—C5—C6	73.8 (2)	C3—C6—C10—O4	65.8 (3)
O1—C3—C6—C10	−86.2 (2)	C5—C6—C10—O4	−45.8 (3)
C7—C3—C6—C10	164.91 (18)	C3—C6—C10—O5	−110.5 (2)
O1—C3—C6—C5	35.06 (19)	C5—C6—C10—O5	137.9 (2)
C7—C3—C6—C5	−73.9 (2)	N3—C1—S1—C2	0.4 (2)
C9—C5—C6—C10	−10.1 (3)	N2—C2—S1—C1	−0.1 (2)
C4—C5—C6—C10	116.51 (19)	N1—C2—S1—C1	179.7 (2)
C9—C5—C6—C3	−126.86 (18)	N1—C2—N2—N3	−179.9 (2)
C4—C5—C6—C3	−0.22 (19)	S1—C2—N2—N3	−0.1 (3)
O1—C3—C7—C8	−34.6 (2)	S1—C1—N3—N2	−0.5 (3)
C6—C3—C7—C8	73.9 (2)	C2—N2—N3—C1	0.4 (3)
C3—C7—C8—C4	0.3 (2)	C7—C3—O1—C4	56.17 (19)
O1—C4—C8—C7	33.9 (2)	C6—C3—O1—C4	−57.40 (18)
C5—C4—C8—C7	−74.5 (2)	C5—C4—O1—C3	57.35 (18)
C4—C5—C9—O3	179.9 (2)	C8—C4—O1—C3	−55.63 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	2.11	2.930 (3)	160
N1—H1C···N3ⁱⁱ	0.86	2.15	2.994 (3)	166
N1—H1C···N2ⁱⁱ	0.86	2.69	3.519 (3)	161
O2—H2A···O1Wⁱⁱⁱ	0.82	1.81	2.626 (2)	176
O5—H5B···N2^iv	0.82	1.85	2.664 (2)	172
O1W—H1WA···O3^v	0.86 (2)	1.91 (2)	2.766 (2)	175 (3)
O1W—H1WB···O4^vi	0.82 (2)	2.51 (3)	3.151 (3)	137 (3)
O1W—H1WB···O1^vi	0.82 (2)	2.55 (3)	3.061 (3)	122 (3)

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

Experimental details

Crystal data
Chemical formula	C₈H₁₀O₅·C₂H₃N₃S·H₂O
M_r	305.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.7678 (5), 18.4267 (15), 12.7546 (11)
β (°)	101.336 (6)
V (Å³)	1329.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.16 × 0.09

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	10820, 2995, 2026
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.133, 1.05
No. of reflections	2995
No. of parameters	187
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	2.11	2.930 (3)	160.4
N1—H1C···N3ⁱⁱ	0.86	2.15	2.994 (3)	165.8
N1—H1C···N2ⁱⁱ	0.86	2.69	3.519 (3)	160.9
O2—H2A···O1Wⁱⁱⁱ	0.82	1.81	2.626 (2)	176.1
O5—H5B···N2^iv	0.82	1.85	2.664 (2)	172.3
O1W—H1WA···O3^v	0.859 (17)	1.910 (17)	2.766 (2)	175 (3)
O1W—H1WB···O4^vi	0.819 (17)	2.51 (3)	3.151 (3)	137 (3)
O1W—H1WB···O1^vi	0.819 (17)	2.55 (3)	3.061 (3)	122 (3)

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

Acknowledgements

The authors thank the Natural Science Foundation of Zhejiang Province, China (grant No. Y407301) for financial support.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shimi, I. R. & Zaki, Z. (1982). Eur. J. Cancer Clin. Oncol. 18, 785–793. CrossRef CAS PubMed Web of Science Google Scholar

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Volume 65| Part 7| July 2009| Page o1590

doi:10.1107/S1600536809021825

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

rac-7-Oxabi­cyclo­[2.2.1]heptane-2,3-di­carboxylic acid–2-amino-1,3,4-thia­diazole–water (1/1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid–2-amino-1,3,4-thiadiazole–water (1/1/1)