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

The title compound, C(8)H(10)O(5)·C(2)H(3)N(3)S·H(2)O, was synthesized by the reaction of 2-amino-1,3,4-thia-diazole 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 inter-actions are observed between symmetry-related thia-diazole ring systems [centroid-centroid distance = 3.9110 (3) Å, inter-planar 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 = 305.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.05

2995 reflections

187 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.29 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H10O5·C2H3N3S·H2O	F(000) = 640
Mr = 305.31	Dx = 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

Bruker APEXII area-detector diffractometer	2995 independent reflections
Radiation source: fine-focus sealed tube	2026 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.949, Tmax = 0.977	k = −24→23
10820 measured reflections	l = −16→15

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(Fo2) + (0.062P)2 + 0.3174P] where P = (Fo2 + 2Fc2)/3
2995 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 0.30 e Å−3
3 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···N2iv	0.82	1.85	2.664 (2)	172
O1W—H1WA···O3v	0.86 (2)	1.91 (2)	2.766 (2)	175 (3)
O1W—H1WB···O4vi	0.82 (2)	2.51 (3)	3.151 (3)	137 (3)
O1W—H1WB···O1vi	0.82 (2)	2.55 (3)	3.061 (3)	122 (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⋯N2iv	0.82	1.85	2.664 (2)	172
O1W—H1WA⋯O3v	0.859 (17)	1.910 (17)	2.766 (2)	175 (3)
O1W—H1WB⋯O4vi	0.819 (17)	2.51 (3)	3.151 (3)	137 (3)
O1W—H1WB⋯O1vi	0.819 (17)	2.55 (3)	3.061 (3)	122 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .