The 1:1 cocrystal of rac-7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxylic acid and 2-amino-benzothia-zole.

In the crystal structure of the title compound, rac-7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxylic acid-2-amino-benzo-thia-zole (1/1), C(8)H(10)O(5)·C(7)H(6)N(2)S, mol-ecules of each component are linked into centrosymmetric dimers by inter-molecular N-H⋯O hydrogen bonds. These dimers are connected by O-H⋯O hydrogen bonds into a chain along the b axis. In addition, π-π inter-actions between aromatic heterocycles occur [centroid-centroid distance of 3.4709 Å and inter-planar spacing of 3.4374 Å between symmetry-related benzothia-zole ring systems.

Related literature

For related literature, see: Liu et al. (2002 ▶).

Experimental

Crystal data

C8H10O5·C7H6N2S

M = 336.36

Triclinic,

a = 8.3082 (1) Å

b = 9.0428 (1) Å

c = 11.0438 (2) Å

α = 67.1546 (8)°

β = 83.0101 (8)°

γ = 86.9193 (9)°

V = 758.92 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 296 (2) K

0.43 × 0.27 × 0.16 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.92, T max = 0.96

11829 measured reflections

3416 independent reflections

2675 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.159

S = 1.06

3416 reflections

214 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −1.05 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536808015365/kp2168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015365/kp2168Isup2.hkl

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

C8H10O5·C7H6N2S	Z = 2
Mr = 336.36	F000 = 352
Triclinic, P1	Dx = 1.472 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3082 (1) Å	Cell parameters from 4303 reflections
b = 9.0428 (1) Å	θ = 2.0–27.4º
c = 11.0438 (2) Å	µ = 0.24 mm−1
α = 67.1546 (8)º	T = 296 (2) K
β = 83.0101 (8)º	Block, colourless
γ = 86.9193 (9)º	0.43 × 0.27 × 0.16 mm
V = 758.93 (2) Å3

Bruker APEXII area-detector diffractometer	3416 independent reflections
Radiation source: fine-focus sealed tube	2675 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 296(2) K	θmax = 27.4º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.92, Tmax = 0.96	k = −11→11
11829 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0773P)2 + 0.3994P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3416 reflections	Δρmax = 0.67 e Å−3
214 parameters	Δρmin = −1.05 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
S1	0.41626 (8)	0.33690 (10)	0.46435 (8)	0.0645 (3)
N1	0.5173 (3)	0.4819 (3)	0.2070 (3)	0.0640 (6)
H1A	0.5827	0.4957	0.1369	0.077*
H1B	0.4338	0.5433	0.2033	0.077*
N2	0.6705 (2)	0.2670 (2)	0.33434 (19)	0.0424 (4)
O1	0.2197 (2)	0.5380 (2)	−0.00822 (19)	0.0616 (5)
O2	0.28892 (19)	1.05947 (19)	−0.01033 (17)	0.0463 (4)
H2	0.385 (2)	1.090 (4)	−0.025 (3)	0.069*
O3	0.1725 (2)	0.7920 (2)	−0.13815 (17)	0.0546 (5)
H3	0.227 (4)	0.770 (4)	−0.200 (3)	0.082*
O4	0.40832 (17)	0.81995 (19)	0.06576 (18)	0.0489 (4)
O5	0.17176 (18)	0.58165 (18)	0.27645 (15)	0.0441 (4)
C1	0.2856 (2)	0.9053 (2)	0.0535 (2)	0.0354 (4)
C2	0.1220 (2)	0.8368 (2)	0.1213 (2)	0.0342 (4)
H2A	0.0424	0.9240	0.1093	0.041*
C3	0.1319 (3)	0.7405 (3)	0.2703 (2)	0.0405 (5)
H3A	0.2094	0.7840	0.3079	0.049*
C4	−0.0397 (3)	0.7220 (3)	0.3424 (2)	0.0486 (6)
H4A	−0.1005	0.8219	0.3116	0.058*
H4B	−0.0381	0.6847	0.4373	0.058*
C5	−0.1091 (3)	0.5947 (3)	0.3034 (3)	0.0498 (6)
H5A	−0.1388	0.4980	0.3802	0.060*
H5B	−0.2028	0.6353	0.2554	0.060*
C6	0.0343 (3)	0.5643 (3)	0.2149 (2)	0.0426 (5)
H6A	0.0305	0.4601	0.2074	0.051*
C7	0.0545 (2)	0.7055 (3)	0.0818 (2)	0.0368 (5)
H7A	−0.0530	0.7396	0.0525	0.044*
C8	0.1598 (3)	0.6691 (3)	−0.0256 (2)	0.0416 (5)
C9	0.5451 (3)	0.3664 (3)	0.3202 (3)	0.0473 (6)
C10	0.6687 (3)	0.1569 (3)	0.4631 (2)	0.0460 (5)
C11	0.7797 (4)	0.0351 (3)	0.5088 (3)	0.0623 (7)
H11A	0.8695	0.0243	0.4536	0.075*
C12	0.7536 (5)	−0.0717 (4)	0.6404 (3)	0.0803 (10)
H12A	0.8273	−0.1547	0.6738	0.096*
C13	0.6181 (5)	−0.0553 (4)	0.7222 (3)	0.0823 (10)
H13A	0.6013	−0.1294	0.8089	0.099*
C14	0.5100 (5)	0.0671 (5)	0.6778 (3)	0.0788 (9)
H14A	0.4208	0.0778	0.7335	0.095*
C15	0.5351 (3)	0.1745 (3)	0.5489 (3)	0.0571 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0463 (4)	0.0910 (6)	0.0724 (5)	−0.0114 (3)	0.0153 (3)	−0.0539 (4)
N1	0.0493 (12)	0.0656 (14)	0.0688 (16)	0.0157 (10)	−0.0021 (11)	−0.0202 (12)
N2	0.0411 (9)	0.0464 (10)	0.0417 (10)	−0.0012 (8)	0.0021 (8)	−0.0211 (9)
O1	0.0721 (12)	0.0542 (10)	0.0538 (11)	0.0143 (9)	0.0059 (9)	−0.0212 (9)
O2	0.0363 (8)	0.0413 (8)	0.0499 (10)	−0.0046 (6)	0.0004 (7)	−0.0062 (7)
O3	0.0684 (11)	0.0541 (10)	0.0368 (9)	0.0106 (8)	0.0043 (8)	−0.0171 (8)
O4	0.0303 (7)	0.0460 (9)	0.0630 (11)	0.0003 (6)	0.0053 (7)	−0.0159 (8)
O5	0.0379 (8)	0.0474 (9)	0.0401 (9)	0.0018 (6)	−0.0035 (6)	−0.0098 (7)
C1	0.0315 (9)	0.0389 (10)	0.0332 (10)	−0.0018 (8)	0.0010 (8)	−0.0122 (8)
C2	0.0265 (9)	0.0372 (10)	0.0373 (11)	0.0009 (7)	0.0013 (7)	−0.0141 (9)
C3	0.0350 (10)	0.0506 (12)	0.0368 (11)	−0.0064 (9)	0.0012 (8)	−0.0184 (10)
C4	0.0433 (12)	0.0602 (14)	0.0400 (12)	−0.0075 (10)	0.0110 (9)	−0.0205 (11)
C5	0.0397 (12)	0.0591 (14)	0.0452 (13)	−0.0140 (10)	0.0079 (10)	−0.0162 (11)
C6	0.0405 (11)	0.0420 (11)	0.0440 (12)	−0.0060 (9)	0.0013 (9)	−0.0162 (10)
C7	0.0296 (9)	0.0447 (11)	0.0378 (11)	−0.0007 (8)	−0.0028 (8)	−0.0181 (9)
C8	0.0381 (11)	0.0503 (13)	0.0394 (12)	0.0028 (9)	−0.0046 (9)	−0.0210 (10)
C9	0.0367 (11)	0.0551 (13)	0.0583 (15)	−0.0070 (10)	0.0065 (10)	−0.0335 (12)
C10	0.0556 (14)	0.0478 (12)	0.0408 (12)	−0.0131 (10)	−0.0007 (10)	−0.0234 (10)
C11	0.088 (2)	0.0553 (15)	0.0482 (15)	−0.0018 (14)	−0.0140 (14)	−0.0224 (12)
C12	0.129 (3)	0.0528 (16)	0.062 (2)	−0.0111 (18)	−0.034 (2)	−0.0174 (15)
C13	0.125 (3)	0.083 (2)	0.0391 (15)	−0.0536 (16)	−0.0057 (17)	−0.0179 (15)
C14	0.091 (2)	0.104 (2)	0.0495 (17)	−0.0510 (15)	0.0100 (14)	−0.0374 (17)
C15	0.0619 (14)	0.0761 (14)	0.0439 (14)	−0.0314 (9)	0.0091 (9)	−0.0351 (11)

S1—C15	1.734 (3)	C4—C5	1.537 (3)
S1—C9	1.743 (2)	C4—H4A	0.9700
N1—C9	1.318 (4)	C4—H4B	0.9700
N1—H1A	0.8600	C5—C6	1.530 (3)
N1—H1B	0.8600	C5—H5A	0.9700
N2—C9	1.322 (3)	C5—H5B	0.9700
N2—C10	1.382 (3)	C6—C7	1.525 (3)
O1—C8	1.214 (3)	C6—H6A	0.9800
O2—C1	1.295 (3)	C7—C8	1.517 (3)
O2—H2	0.836 (18)	C7—H7A	0.9800
O3—C8	1.303 (3)	C10—C11	1.375 (4)
O3—H3	0.854 (18)	C10—C15	1.413 (3)
O4—C1	1.234 (2)	C11—C12	1.396 (4)
O5—C3	1.434 (3)	C11—H11A	0.9300
O5—C6	1.443 (3)	C12—C13	1.395 (6)
C1—C2	1.508 (3)	C12—H12A	0.9300
C2—C3	1.544 (3)	C13—C14	1.361 (5)
C2—C7	1.565 (3)	C13—H13A	0.9300
C2—H2A	0.9800	C14—C15	1.374 (4)
C3—C4	1.530 (3)	C14—H14A	0.9300
C3—H3A	0.9800
C15—S1—C9	89.18 (12)	O5—C6—C5	102.47 (18)
C9—N1—H1A	120.0	C7—C6—C5	110.16 (19)
C9—N1—H1B	120.0	O5—C6—H6A	113.6
H1A—N1—H1B	120.0	C7—C6—H6A	113.6
C9—N2—C10	111.49 (19)	C5—C6—H6A	113.6
C1—O2—H2	109 (2)	C8—C7—C6	114.11 (18)
C8—O3—H3	112 (2)	C8—C7—C2	115.16 (16)
C3—O5—C6	96.24 (15)	C6—C7—C2	101.23 (17)
O4—C1—O2	123.04 (18)	C8—C7—H7A	108.7
O4—C1—C2	121.43 (18)	C6—C7—H7A	108.7
O2—C1—C2	115.39 (17)	C2—C7—H7A	108.7
C1—C2—C3	110.23 (17)	O1—C8—O3	124.6 (2)
C1—C2—C7	116.64 (16)	O1—C8—C7	123.1 (2)
C3—C2—C7	100.43 (16)	O3—C8—C7	112.29 (18)
C1—C2—H2A	109.7	N1—C9—N2	123.7 (2)
C3—C2—H2A	109.7	N1—C9—S1	121.07 (18)
C7—C2—H2A	109.7	N2—C9—S1	115.2 (2)
O5—C3—C4	103.13 (17)	C11—C10—N2	125.6 (2)
O5—C3—C2	102.91 (16)	C11—C10—C15	120.4 (2)
C4—C3—C2	108.53 (18)	N2—C10—C15	114.0 (2)
O5—C3—H3A	113.7	C10—C11—C12	118.0 (3)
C4—C3—H3A	113.7	C10—C11—H11A	121.0
C2—C3—H3A	113.7	C12—C11—H11A	121.0
C3—C4—C5	101.17 (18)	C11—C12—C13	120.6 (3)
C3—C4—H4A	111.5	C11—C12—H12A	119.7
C5—C4—H4A	111.5	C13—C12—H12A	119.7
C3—C4—H4B	111.5	C14—C13—C12	121.3 (3)
C5—C4—H4B	111.5	C14—C13—H13A	119.3
H4A—C4—H4B	109.4	C12—C13—H13A	119.3
C6—C5—C4	101.63 (17)	C13—C14—C15	118.7 (3)
C6—C5—H5A	111.4	C13—C14—H14A	120.6
C4—C5—H5A	111.4	C15—C14—H14A	120.6
C6—C5—H5B	111.4	C14—C15—C10	120.9 (3)
C4—C5—H5B	111.4	C14—C15—S1	128.9 (3)
H5A—C5—H5B	109.3	C10—C15—S1	110.1 (2)
O5—C6—C7	102.38 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.13	2.953 (3)	161
N1—H1B···O5	0.86	2.29	3.061 (3)	150
N1—H1B···O4	0.86	2.38	2.991 (3)	128
O2—H2···O4ii	0.836 (18)	1.868 (18)	2.700 (2)	174 (3)
O3—H3···N2i	0.854 (18)	1.758 (19)	2.611 (2)	176 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.13	2.953 (3)	161
N1—H1B⋯O5	0.86	2.29	3.061 (3)	150
N1—H1B⋯O4	0.86	2.38	2.991 (3)	128
O2—H2⋯O4ii	0.836 (18)	1.868 (18)	2.700 (2)	174 (3)
O3—H3⋯N2i	0.854 (18)	1.758 (19)	2.611 (2)	176 (4)

Symmetry codes: (i) ; (ii) .