Triaqua-(7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxyl-ato-κO,O,O)cobalt(II) monohydrate.

The title complex, [Co(C(8)H(8)O(5))(H(2)O)(3)]·H(2)O, was synthesized by reaction of cobalt acetate with 7-oxabicyclo-[2.2.1]heptane-2,3-dicarb-oxy-lic anhydride (norcantharidin) in aqueous solution. In the mol-ecule, the Co(II) atom is six-coordinated in a distorted octa-hedral environment, binding to the bridging O atom of the bicyclo-heptane unit, to two O atoms from monodentate carboxyl-ate groups and to three water O atoms. The crystal structure is stabilized by several O-H⋯O hydrogen-bonding inter-actions involving both the coordinated and uncoordinated water mol-ecules as donors and the carboxyl-ate O atoms of neighbouring mol-ecules as acceptors.

Related literature

For background to the applications of norcantharidin, see: Jiao et al. (2005 ▶); Wang (1989 ▶). For related structures, see: Wang et al. (2010 ▶); Kaplonek et al. (1994 ▶).

Experimental

Crystal data

[Co(C8H8O5)(H2O)3]·H2O

M = 315.14

Monoclinic,

a = 10.0965 (3) Å

b = 10.0208 (3) Å

c = 14.5893 (3) Å

β = 129.177 (1)°

V = 1144.25 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.54 mm−1

T = 296 K

0.24 × 0.17 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.745, T max = 0.824

14892 measured reflections

2004 independent reflections

1861 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.063

S = 1.08

2004 reflections

163 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028431/wm2510sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028431/wm2510Isup2.hkl

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

[Co(C8H8O5)(H2O)3]·H2O	F(000) = 652
Mr = 315.14	Dx = 1.829 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8994 reflections
a = 10.0965 (3) Å	θ = 2.6–25.0°
b = 10.0208 (3) Å	µ = 1.54 mm−1
c = 14.5893 (3) Å	T = 296 K
β = 129.177 (1)°	Block, red
V = 1144.25 (5) Å3	0.24 × 0.17 × 0.13 mm
Z = 4

Bruker SMART CCD diffractometer	2004 independent reflections
Radiation source: fine-focus sealed tube	1861 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.745, Tmax = 0.824	k = −11→11
14892 measured reflections	l = −16→17

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0277P)2 + 1.0316P] where P = (Fo2 + 2Fc2)/3
2004 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.28 e Å−3
4 restraints	Δρmin = −0.30 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
Co1	0.75127 (3)	0.93105 (2)	0.50125 (2)	0.01957 (10)
O1	0.78435 (19)	0.89643 (14)	0.37592 (12)	0.0290 (3)
O1W	0.7237 (2)	1.13465 (15)	0.47074 (14)	0.0427 (4)
H1WA	0.7016	1.1781	0.4125	0.064*
H1WB	0.7586	1.1869	0.5279	0.064*
O2	0.7679 (2)	0.77531 (16)	0.24295 (14)	0.0442 (4)
O2W	1.01188 (18)	0.94437 (15)	0.63877 (13)	0.0348 (4)
H2WA	1.0847	0.9886	0.6399	0.052*
H2WB	1.0612	0.8811	0.6887	0.052*
O3	0.49581 (17)	0.89349 (14)	0.36612 (12)	0.0281 (3)
O3W	0.71943 (19)	0.95345 (14)	0.62906 (13)	0.0301 (3)
H3WA	0.6499	1.0012	0.6291	0.045*
H3WB	0.7291	0.8840	0.6664	0.045*
O4	0.3105 (2)	0.79264 (17)	0.19436 (13)	0.0465 (4)
O4W	1.1014 (2)	0.73049 (16)	0.79981 (13)	0.0387 (4)
H4WA	1.1328	0.6564	0.7907	0.058*
H4WB	0.9987	0.7184	0.7718	0.058*
O5	0.78301 (16)	0.72157 (12)	0.54243 (11)	0.0191 (3)
C1	0.8565 (2)	0.64609 (19)	0.49869 (16)	0.0215 (4)
H1A	0.9702	0.6772	0.5300	0.026*
C2	0.7198 (2)	0.66254 (18)	0.36363 (16)	0.0206 (4)
H2A	0.7197	0.5836	0.3239	0.025*
C3	0.5510 (2)	0.66506 (18)	0.34899 (16)	0.0199 (4)
H3A	0.4794	0.5884	0.3014	0.024*
C4	0.6238 (2)	0.64553 (19)	0.47793 (16)	0.0209 (4)
H4A	0.5468	0.6757	0.4930	0.025*
C5	0.6883 (3)	0.5032 (2)	0.51937 (18)	0.0277 (4)
H5A	0.6075	0.4384	0.4603	0.033*
H5B	0.7105	0.4842	0.5932	0.033*
C6	0.8554 (3)	0.5040 (2)	0.53581 (18)	0.0276 (4)
H6A	0.9543	0.4871	0.6174	0.033*
H6B	0.8519	0.4386	0.4853	0.033*
C7	0.7572 (2)	0.7867 (2)	0.32282 (17)	0.0242 (4)
C8	0.4448 (2)	0.79295 (19)	0.29760 (16)	0.0233 (4)

	U11	U22	U33	U12	U13	U23
Co1	0.02472 (16)	0.01767 (16)	0.01900 (16)	−0.00126 (9)	0.01509 (13)	−0.00144 (9)
O1	0.0461 (9)	0.0229 (7)	0.0333 (8)	−0.0087 (6)	0.0323 (7)	−0.0060 (6)
O1W	0.0740 (12)	0.0193 (8)	0.0271 (8)	−0.0025 (7)	0.0282 (8)	−0.0008 (6)
O2	0.0791 (12)	0.0378 (9)	0.0462 (10)	−0.0240 (8)	0.0541 (10)	−0.0165 (7)
O2W	0.0263 (8)	0.0363 (8)	0.0347 (8)	−0.0067 (6)	0.0159 (7)	0.0062 (7)
O3	0.0255 (7)	0.0237 (7)	0.0278 (7)	0.0043 (6)	0.0133 (6)	−0.0037 (6)
O3W	0.0423 (9)	0.0299 (8)	0.0340 (8)	0.0112 (6)	0.0316 (7)	0.0079 (6)
O4	0.0431 (9)	0.0399 (9)	0.0229 (8)	0.0156 (8)	0.0050 (7)	−0.0029 (7)
O4W	0.0385 (9)	0.0376 (9)	0.0319 (8)	0.0052 (7)	0.0184 (7)	0.0049 (7)
O5	0.0211 (6)	0.0202 (7)	0.0193 (6)	0.0001 (5)	0.0143 (5)	−0.0006 (5)
C1	0.0207 (9)	0.0226 (10)	0.0260 (10)	0.0009 (8)	0.0171 (8)	−0.0017 (8)
C2	0.0252 (10)	0.0199 (9)	0.0236 (9)	−0.0014 (7)	0.0187 (8)	−0.0033 (7)
C3	0.0211 (9)	0.0180 (9)	0.0221 (9)	−0.0022 (7)	0.0143 (8)	−0.0024 (7)
C4	0.0207 (9)	0.0222 (9)	0.0246 (9)	−0.0016 (8)	0.0166 (8)	0.0004 (8)
C5	0.0328 (11)	0.0224 (10)	0.0317 (11)	−0.0002 (8)	0.0221 (10)	0.0059 (8)
C6	0.0273 (10)	0.0221 (10)	0.0304 (10)	0.0055 (8)	0.0168 (9)	0.0031 (8)
C7	0.0283 (10)	0.0266 (10)	0.0245 (10)	−0.0051 (8)	0.0200 (9)	−0.0036 (8)
C8	0.0235 (10)	0.0246 (10)	0.0220 (10)	0.0015 (8)	0.0144 (9)	0.0010 (8)

Co1—O3	2.0631 (14)	O5—C1	1.459 (2)
Co1—O1W	2.0691 (15)	O5—C4	1.462 (2)
Co1—O2W	2.0728 (15)	C1—C6	1.526 (3)
Co1—O1	2.0849 (13)	C1—C2	1.542 (3)
Co1—O3W	2.0948 (13)	C1—H1A	0.9800
Co1—O5	2.1510 (13)	C2—C7	1.526 (3)
O1—C7	1.271 (2)	C2—C3	1.578 (2)
O1W—H1WA	0.8500	C2—H2A	0.9800
O1W—H1WB	0.8500	C3—C8	1.529 (3)
O2—C7	1.241 (2)	C3—C4	1.540 (3)
O2W—H2WA	0.8499	C3—H3A	0.9800
O2W—H2WB	0.8500	C4—C5	1.526 (3)
O3—C8	1.276 (2)	C4—H4A	0.9800
O3W—H3WA	0.8501	C5—C6	1.547 (3)
O3W—H3WB	0.8499	C5—H5A	0.9700
O4—C8	1.236 (2)	C5—H5B	0.9700
O4W—H4WA	0.8500	C6—H6A	0.9700
O4W—H4WB	0.8499	C6—H6B	0.9700
O3—Co1—O1W	93.29 (6)	C7—C2—C1	110.07 (15)
O3—Co1—O2W	173.18 (6)	C7—C2—C3	116.49 (15)
O1W—Co1—O2W	93.48 (6)	C1—C2—C3	101.13 (14)
O3—Co1—O1	85.86 (6)	C7—C2—H2A	109.6
O1W—Co1—O1	92.85 (6)	C1—C2—H2A	109.6
O2W—Co1—O1	92.92 (6)	C3—C2—H2A	109.6
O3—Co1—O3W	93.90 (6)	C8—C3—C4	110.57 (15)
O1W—Co1—O3W	90.60 (6)	C8—C3—C2	116.27 (15)
O2W—Co1—O3W	86.92 (6)	C4—C3—C2	101.03 (14)
O1—Co1—O3W	176.55 (5)	C8—C3—H3A	109.5
O3—Co1—O5	87.97 (5)	C4—C3—H3A	109.5
O1W—Co1—O5	176.73 (5)	C2—C3—H3A	109.5
O2W—Co1—O5	85.32 (5)	O5—C4—C5	102.24 (14)
O1—Co1—O5	90.25 (5)	O5—C4—C3	101.68 (13)
O3W—Co1—O5	86.30 (5)	C5—C4—C3	110.98 (15)
C7—O1—Co1	125.88 (12)	O5—C4—H4A	113.6
Co1—O1W—H1WA	129.4	C5—C4—H4A	113.6
Co1—O1W—H1WB	118.7	C3—C4—H4A	113.6
H1WA—O1W—H1WB	110.5	C4—C5—C6	101.94 (15)
Co1—O2W—H2WA	127.3	C4—C5—H5A	111.4
Co1—O2W—H2WB	118.7	C6—C5—H5A	111.4
H2WA—O2W—H2WB	109.9	C4—C5—H5B	111.4
C8—O3—Co1	122.32 (12)	C6—C5—H5B	111.4
Co1—O3W—H3WA	130.7	H5A—C5—H5B	109.2
Co1—O3W—H3WB	117.5	C1—C6—C5	101.65 (15)
H3WA—O3W—H3WB	102.8	C1—C6—H6A	111.4
H4WA—O4W—H4WB	105.2	C5—C6—H6A	111.4
C1—O5—C4	95.99 (13)	C1—C6—H6B	111.4
C1—O5—Co1	114.26 (10)	C5—C6—H6B	111.4
C4—O5—Co1	114.80 (10)	H6A—C6—H6B	109.3
O5—C1—C6	102.04 (14)	O2—C7—O1	122.60 (18)
O5—C1—C2	102.20 (14)	O2—C7—C2	118.71 (17)
C6—C1—C2	110.60 (16)	O1—C7—C2	118.60 (15)
O5—C1—H1A	113.6	O4—C8—O3	123.07 (18)
C6—C1—H1A	113.6	O4—C8—C3	119.02 (17)
C2—C1—H1A	113.6	O3—C8—C3	117.81 (16)
O3—Co1—O1—C7	−63.86 (16)	C1—C2—C3—C4	−1.55 (16)
O1W—Co1—O1—C7	−156.95 (17)	C1—O5—C4—C5	56.17 (15)
O2W—Co1—O1—C7	109.42 (16)	Co1—O5—C4—C5	176.41 (10)
O5—Co1—O1—C7	24.09 (16)	C1—O5—C4—C3	−58.60 (15)
O1W—Co1—O3—C8	140.00 (15)	Co1—O5—C4—C3	61.65 (14)
O1—Co1—O3—C8	47.38 (15)	C8—C3—C4—O5	−87.05 (16)
O3W—Co1—O3—C8	−129.17 (15)	C2—C3—C4—O5	36.63 (16)
O5—Co1—O3—C8	−43.02 (15)	C8—C3—C4—C5	164.82 (15)
O3—Co1—O5—C1	101.16 (11)	C2—C3—C4—C5	−71.49 (17)
O2W—Co1—O5—C1	−77.59 (12)	O5—C4—C5—C6	−33.84 (17)
O1—Co1—O5—C1	15.31 (12)	C3—C4—C5—C6	73.92 (18)
O3W—Co1—O5—C1	−164.80 (12)	O5—C1—C6—C5	35.70 (17)
O3—Co1—O5—C4	−8.38 (11)	C2—C1—C6—C5	−72.42 (18)
O2W—Co1—O5—C4	172.87 (11)	C4—C5—C6—C1	−1.04 (18)
O1—Co1—O5—C4	−94.23 (11)	Co1—O1—C7—O2	174.77 (16)
O3W—Co1—O5—C4	85.66 (11)	Co1—O1—C7—C2	−8.7 (3)
C4—O5—C1—C6	−56.90 (15)	C1—C2—C7—O2	126.16 (19)
Co1—O5—C1—C6	−177.57 (11)	C3—C2—C7—O2	−119.5 (2)
C4—O5—C1—C2	57.57 (15)	C1—C2—C7—O1	−50.5 (2)
Co1—O5—C1—C2	−63.10 (14)	C3—C2—C7—O1	63.9 (2)
O5—C1—C2—C7	89.68 (16)	Co1—O3—C8—O4	−151.18 (17)
C6—C1—C2—C7	−162.30 (15)	Co1—O3—C8—C3	32.4 (2)
O5—C1—C2—C3	−34.10 (16)	C4—C3—C8—O4	−140.06 (19)
C6—C1—C2—C3	73.92 (17)	C2—C3—C8—O4	105.6 (2)
C7—C2—C3—C8	−1.1 (2)	C4—C3—C8—O3	36.5 (2)
C1—C2—C3—C8	118.14 (16)	C2—C3—C8—O3	−77.9 (2)
C7—C2—C3—C4	−120.82 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WB···O4W	0.85	2.06	2.872 (2)	160.
O4W—H4WB···O5	0.85	2.60	3.0316 (19)	113.
O1W—H1WA···O4i	0.85	1.88	2.716 (2)	169.
O1W—H1WB···O4Wii	0.85	2.00	2.789 (2)	153.
O2W—H2WA···O1iii	0.85	1.87	2.7168 (19)	171.
O3W—H3WB···O2iv	0.85	1.84	2.688 (2)	173.
O4W—H4WB···O2iv	0.85	2.09	2.916 (2)	164.
O3W—H3WA···O3v	0.85	1.85	2.6969 (19)	178.
O4W—H4WA···O3Wvi	0.85	2.35	3.112 (2)	149.

Table 1

Selected bond lengths (Å)

Co1—O3	2.0631 (14)
Co1—O1W	2.0691 (15)
Co1—O2W	2.0728 (15)
Co1—O1	2.0849 (13)
Co1—O3W	2.0948 (13)
Co1—O5	2.1510 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2WB⋯O4W	0.85	2.06	2.872 (2)	160
O4W—H4WB⋯O5	0.85	2.60	3.0316 (19)	113
O1W—H1WA⋯O4i	0.85	1.88	2.716 (2)	169
O1W—H1WB⋯O4Wii	0.85	2.00	2.789 (2)	153
O2W—H2WA⋯O1iii	0.85	1.87	2.7168 (19)	171
O3W—H3WB⋯O2iv	0.85	1.84	2.688 (2)	173
O4W—H4WB⋯O2iv	0.85	2.09	2.916 (2)	164
O3W—H3WA⋯O3v	0.85	1.85	2.6969 (19)	178
O4W—H4WA⋯O3Wvi	0.85	2.35	3.112 (2)	149

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