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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page m488
doi:10.1107/S1600536811009925

catena-Poly[[di­aqua­cobalt(II)]bis­­[μ-2-(4-carboxyl­atophen­yl)-4,4,5,5-tetra­methyl-4,5-di­hydro-1H-imidazol-1-oxyl 3-oxide]]

Rong Rong,a Ge Gaob* and Lili Zhuc

aDepartment of Chemistry, Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China, bOrdered Matter Science Research Center, Department of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and cSchool of Chemistry and Materials Science, Huaibei Normal University, Anhui 235000, People's Republic of China
*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 28 February 2011; accepted 16 March 2011; online 26 March 2011)

In the title compound, [Co(C14H16N2O4)2(H2O)2]n, the CoII atom, lying on an inversion center, is coordinated by six O atoms in a distorted octa­hedral geometry. The CoII atoms are bridged by the nitronyl nitroxide ligands into a tape-like structure along the b axis. The tapes are further connected by O—H⋯O hydrogen bonds, forming a layer parallel to the bc plane.

Related literature

For related structures, see: Caneschi et al. (1993[Caneschi, A., Chiesi, P., David, L., Ferraro, F., Gatteschi, D. & Sessoli, R. (1993). Inorg. Chem. 32, 1445-1453.]); Luneau et al. (1998[Luneau, D., Romero, F. M. & Ziessel, R. (1998). Inorg. Chem. 37, 5078-5087.]). For the synthesis of [Co(C5H9O2)2(H2O)2], see: Mehrotra & Bohra (1983[Mehrotra, R. C. & Bohra, R. (1983). Metal Carboxylates, Academic Press: London.]). For the synthesis of 2-(4-carb­oxy­phen­yl)-4,4,5,5-tetra­methyl-4,5-dihydro-1H-imidazol-1-oxyl-3-oxide, see: Schiødt et al. (1996[Schiødt, N. C., Fabrizi de Biani, F., Caneschi, A. & Gatteschi, D. (1996). Inorg. Chim. Acta, 248, 139-146.]).

[Scheme 1]

Experimental

Crystal data

  • [Co(C14H16N2O4)2(H2O)2]

  • Mr = 647.54

  • Monoclinic, P 21 /c

  • a = 13.548 (3) Å

  • b = 9.2054 (18) Å

  • c = 12.549 (3) Å

  • β = 115.17 (3)°

  • V = 1416.5 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.67 mm−1

  • T = 293 K

  • 0.43 × 0.42 × 0.20 mm
Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.240, Tmax = 0.428

  • 14419 measured reflections

  • 3241 independent reflections

  • 2050 reflections with I > 2σ(I)

  • Rint = 0.121
Refinement

  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.169

  • S = 1.04

  • 3241 reflections

  • 196 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H1O5⋯O2i 0.87 2.31 2.736 (4) 111
O5—H2O5⋯O2ii 0.85 2.40 2.886 (4) 117
Symmetry codes: (i) -x+1, -y-1, -z+2; (ii) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009925/is2683sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009925/is2683Isup2.hkl

checkCIF report


Comment top

The combination of paramagnetic metal ions and organic nitronyl nitroxides has attracted much more attention in the last decades, because of their intriguing structural, magnetic, and spectral properties (Caneschi et al., 1993; Luneau et al., 1998).

We herein report the crystal structure of a new complex revealed two ladder-like one-dimensional chains of repeating Co(NITpBA)2(H2O)2 units. As shown in Fig. 1, the central Co ion is located in a distorted octahedral environment. It is bonded to two oxygen atoms from carboxylic acid group, two oxygen atoms from nitroxide group and two oxygen atoms from two water atoms. Each radical coordinates the next Co(II) ion in the opposite fashion thus forming chains. There are intermolecular hydrogen bonds between the coordinated water molecule and the non-coordinated carboxylic O2 atom (Table 1 and Fig. 2).

Related literature top

For related structures, see: Caneschi et al. (1993); Luneau et al. (1998). For the synthesis of [Co(C5H9O2)2(H2O)2], see: Mehrotra & Bohra (1983). For the synthesis of 2-(4-carboxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl-3-oxide, see: Schiødt et al. (1996).

Experimental top

All reagents and chemicals were purchased from commercial sources. The carboxylates, Co(Me3CCO2)2(H2O)2, were prepared as described previously (Mehrotra & Bohra, 1983). The benzoic acid substituted nitronyl nitroxide radical NITpBAH) was synthesized according to the procedure previously described (Schiødt et al., 1996). Co(Me3CCO2)2(H2O)2 (0.0290 g, 0.1 mmol) was dissolved with prolonged stirring at room temperature in acetonitrile (15 mL). Then a 10 mL dichloromethane solution of NITpBAH(0.0608 g, 0.2 mmol) was added dropwise with stirring. Both solutions were mixed while stirring was continued for 1 h, dark blue crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature over several days.

Refinement top

Positional parameters of all H atoms bound to C were calculated geometrically (C—H = 0.93 or 0.96 Å) and the H atoms were refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The H atoms of water molecile were located in a difference Fourier map and fixed at the positions with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme and all hydrogen atoms. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing view of the title compound. Hydrogen bonds are shown as dashed lines.
catena-Poly[[diaquacobalt(II)]bis[µ-2-(4-carboxylatophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl 3-oxide]] top
Crystal data top
[Co(C14H16N2O4)2(H2O)2]F(000) = 678
Mr = 647.54Dx = 1.518 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14419 reflections
a = 13.548 (3) Åθ = 3.3–27.5°
b = 9.2054 (18) ŵ = 0.67 mm−1
c = 12.549 (3) ÅT = 293 K
β = 115.17 (3)°Prism, dark blue
V = 1416.5 (5) Å30.43 × 0.42 × 0.20 mm
Z = 2
Data collection top
Rigaku SCXmini
diffractometer		3241 independent reflections
Radiation source: fine-focus sealed tube2050 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.121
Detector resolution: 8.192 pixels mm-1θmax = 27.5°, θmin = 3.3°
ω scansh = −17→17
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −11→11
Tmin = 0.240, Tmax = 0.428l = −16→16
14419 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0616P)2 + 1.8428P]
where P = (Fo2 + 2Fc2)/3
3241 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.54 e Å−3
Crystal data top
[Co(C14H16N2O4)2(H2O)2]V = 1416.5 (5) Å3
Mr = 647.54Z = 2
Monoclinic, P21/cMo Kα radiation
a = 13.548 (3) ŵ = 0.67 mm−1
b = 9.2054 (18) ÅT = 293 K
c = 12.549 (3) Å0.43 × 0.42 × 0.20 mm
β = 115.17 (3)°
Data collection top
Rigaku SCXmini
diffractometer		3241 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2050 reflections with I > 2σ(I)
Tmin = 0.240, Tmax = 0.428Rint = 0.121
14419 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.04Δρmax = 0.54 e Å−3
3241 reflectionsΔρmin = −0.54 e Å−3
196 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
xyzUiso*/Ueq
O10.4450 (2)−0.2949 (3)0.9518 (2)0.0274 (7)
O20.4582 (3)−0.2604 (3)0.7820 (3)0.0364 (8)
O30.0826 (3)0.3058 (4)0.6289 (3)0.0442 (9)
O40.3405 (2)0.4447 (3)0.9959 (2)0.0279 (7)
O50.5531 (2)−0.4483 (3)1.1813 (2)0.0297 (7)
H1O50.6060−0.51051.20770.045*
H2O50.5186−0.45781.22370.045*
N10.1342 (3)0.3787 (4)0.7227 (3)0.0267 (8)
N20.2516 (3)0.4405 (4)0.8999 (3)0.0233 (8)
C10.4323 (3)−0.2209 (4)0.8615 (4)0.0246 (9)
C20.3798 (3)−0.0740 (4)0.8520 (4)0.0234 (9)
C30.3428 (3)0.0019 (4)0.7470 (4)0.0264 (9)
H3A0.3513−0.03800.68340.032*
C40.2933 (4)0.1363 (4)0.7352 (4)0.0284 (10)
H4A0.26870.18610.66400.034*
C50.2805 (3)0.1961 (4)0.8299 (4)0.0229 (9)
C60.3184 (4)0.1222 (4)0.9369 (4)0.0278 (10)
H6A0.31150.16341.00110.033*
C70.3663 (3)−0.0122 (4)0.9470 (4)0.0265 (9)
H7A0.3900−0.06261.01770.032*
C80.2253 (3)0.3363 (4)0.8166 (3)0.0232 (9)
C90.1031 (4)0.5322 (4)0.7365 (4)0.0271 (10)
C100.1582 (3)0.5441 (4)0.8726 (4)0.0266 (10)
C110.1545 (4)0.6293 (5)0.6754 (4)0.0451 (13)
H11A0.11670.61660.59170.068*
H11B0.22980.60350.70100.068*
H11C0.14940.72900.69490.068*
C12−0.0192 (4)0.5491 (6)0.6821 (4)0.0458 (13)
H12A−0.04720.54040.59810.069*
H12B−0.03770.64280.70180.069*
H12C−0.05060.47480.71180.069*
C130.0892 (4)0.4805 (5)0.9312 (5)0.0414 (12)
H13A0.12740.49101.01510.062*
H13B0.07600.37940.91170.062*
H13C0.02090.53120.90370.062*
C140.1972 (4)0.6944 (5)0.9213 (4)0.0392 (12)
H14A0.22990.69101.00580.059*
H14C0.13630.76000.89440.059*
H14D0.25000.72760.89460.059*
Co10.5000−0.50001.00000.0250 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0352 (17)0.0148 (15)0.0341 (16)0.0060 (12)0.0165 (14)0.0051 (12)
O20.058 (2)0.0235 (17)0.0439 (19)0.0125 (15)0.0372 (17)0.0067 (14)
O30.041 (2)0.035 (2)0.0384 (19)0.0023 (16)−0.0002 (16)−0.0109 (15)
O40.0256 (17)0.0295 (16)0.0250 (16)0.0007 (13)0.0074 (13)−0.0007 (12)
O50.0334 (18)0.0258 (16)0.0338 (17)0.0024 (13)0.0181 (14)0.0013 (13)
N10.028 (2)0.0211 (19)0.0277 (19)0.0002 (15)0.0080 (16)−0.0034 (15)
N20.0203 (19)0.0190 (18)0.0300 (19)0.0020 (14)0.0101 (16)−0.0012 (15)
C10.027 (2)0.014 (2)0.033 (2)0.0016 (17)0.013 (2)0.0032 (17)
C20.024 (2)0.015 (2)0.032 (2)0.0016 (17)0.0124 (18)0.0012 (17)
C30.034 (2)0.020 (2)0.030 (2)0.002 (2)0.0190 (19)0.0013 (19)
C40.038 (3)0.018 (2)0.030 (2)0.0046 (19)0.016 (2)0.0054 (18)
C50.021 (2)0.013 (2)0.033 (2)0.0029 (16)0.0094 (18)0.0015 (17)
C60.035 (3)0.020 (2)0.029 (2)−0.0006 (18)0.014 (2)−0.0041 (17)
C70.030 (2)0.021 (2)0.026 (2)0.0008 (19)0.0094 (18)0.0049 (18)
C80.023 (2)0.018 (2)0.027 (2)−0.0004 (17)0.0092 (18)−0.0028 (17)
C90.028 (2)0.015 (2)0.034 (2)0.0058 (16)0.009 (2)0.0009 (17)
C100.027 (2)0.018 (2)0.035 (2)0.0061 (17)0.014 (2)0.0010 (17)
C110.060 (4)0.032 (3)0.044 (3)0.005 (2)0.023 (3)0.011 (2)
C120.035 (3)0.035 (3)0.053 (3)0.011 (2)0.004 (2)−0.002 (2)
C130.041 (3)0.042 (3)0.052 (3)0.005 (2)0.030 (3)0.006 (2)
C140.038 (3)0.029 (3)0.045 (3)0.001 (2)0.012 (2)−0.008 (2)
Co10.0304 (5)0.0162 (4)0.0263 (4)0.0034 (4)0.0101 (4)0.0022 (3)
Geometric parameters (Å, º) top
O1—C11.269 (5)C6—H6A0.9300
O1—Co12.026 (3)C7—H7A0.9300
O2—C11.244 (5)C9—C121.508 (6)
O3—N11.274 (4)C9—C111.525 (6)
O4—N21.292 (4)C9—C101.550 (6)
O4—Co1i2.199 (3)C10—C141.514 (6)
O5—Co12.127 (3)C10—C131.531 (6)
O5—H1O50.8657C11—H11A0.9600
O5—H2O50.8506C11—H11B0.9600
N1—C81.352 (5)C11—H11C0.9600
N1—C91.505 (5)C12—H12A0.9600
N2—C81.350 (5)C12—H12B0.9600
N2—C101.503 (5)C12—H12C0.9600
C1—C21.508 (5)C13—H13A0.9600
C2—C31.383 (5)C13—H13B0.9600
C2—C71.401 (6)C13—H13C0.9600
C3—C41.385 (6)C14—H14A0.9600
C3—H3A0.9300C14—H14C0.9600
C4—C51.386 (6)C14—H14D0.9600
C4—H4A0.9300Co1—O1ii2.026 (3)
C5—C61.394 (5)Co1—O5ii2.127 (3)
C5—C81.465 (5)Co1—O4iii2.199 (3)
C6—C71.378 (6)Co1—O4iv2.199 (3)
C1—O1—Co1131.3 (3)C14—C10—C13109.6 (4)
N2—O4—Co1i123.0 (2)N2—C10—C999.8 (3)
Co1—O5—H1O596.3C14—C10—C9115.5 (4)
Co1—O5—H2O5128.4C13—C10—C9113.3 (4)
H1O5—O5—H2O5106.2C9—C11—H11A109.5
O3—N1—C8126.3 (3)C9—C11—H11B109.5
O3—N1—C9122.0 (3)H11A—C11—H11B109.5
C8—N1—C9111.5 (3)C9—C11—H11C109.5
O4—N2—C8125.3 (3)H11A—C11—H11C109.5
O4—N2—C10123.6 (3)H11B—C11—H11C109.5
C8—N2—C10110.8 (3)C9—C12—H12A109.5
O2—C1—O1125.5 (4)C9—C12—H12B109.5
O2—C1—C2118.9 (4)H12A—C12—H12B109.5
O1—C1—C2115.6 (4)C9—C12—H12C109.5
C3—C2—C7118.7 (4)H12A—C12—H12C109.5
C3—C2—C1119.7 (4)H12B—C12—H12C109.5
C7—C2—C1121.6 (4)C10—C13—H13A109.5
C2—C3—C4121.1 (4)C10—C13—H13B109.5
C2—C3—H3A119.5H13A—C13—H13B109.5
C4—C3—H3A119.5C10—C13—H13C109.5
C3—C4—C5119.6 (4)H13A—C13—H13C109.5
C3—C4—H4A120.2H13B—C13—H13C109.5
C5—C4—H4A120.2C10—C14—H14A109.5
C4—C5—C6120.2 (4)C10—C14—H14C109.5
C4—C5—C8119.8 (4)H14A—C14—H14C109.5
C6—C5—C8120.0 (4)C10—C14—H14D109.5
C7—C6—C5119.5 (4)H14A—C14—H14D109.5
C7—C6—H6A120.2H14C—C14—H14D109.5
C5—C6—H6A120.2O1ii—Co1—O1180.000 (1)
C6—C7—C2120.9 (4)O1ii—Co1—O5ii91.43 (11)
C6—C7—H7A119.5O1—Co1—O5ii88.57 (11)
C2—C7—H7A119.5O1ii—Co1—O588.57 (11)
N2—C8—N1108.2 (3)O1—Co1—O591.43 (11)
N2—C8—C5125.7 (4)O5ii—Co1—O5180.000 (1)
N1—C8—C5125.9 (4)O1ii—Co1—O4iii91.38 (11)
N1—C9—C12110.6 (4)O1—Co1—O4iii88.62 (11)
N1—C9—C11106.4 (4)O5ii—Co1—O4iii92.34 (11)
C12—C9—C11111.1 (4)O5—Co1—O4iii87.66 (11)
N1—C9—C1099.6 (3)O1ii—Co1—O4iv88.62 (11)
C12—C9—C10114.4 (4)O1—Co1—O4iv91.38 (11)
C11—C9—C10113.8 (4)O5ii—Co1—O4iv87.66 (11)
N2—C10—C14111.9 (4)O5—Co1—O4iv92.34 (11)
N2—C10—C13106.0 (3)O4iii—Co1—O4iv180.000 (1)
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y−1, −z+2; (iii) x, y−1, z; (iv) −x+1, −y, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H1O5···O2ii0.872.312.736 (4)111
O5—H2O5···O2v0.852.402.886 (4)117
Symmetry codes: (ii) −x+1, −y−1, −z+2; (v) x, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Co(C14H16N2O4)2(H2O)2]
Mr647.54
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.548 (3), 9.2054 (18), 12.549 (3)
β (°) 115.17 (3)
V (Å3)1416.5 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.67
Crystal size (mm)0.43 × 0.42 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.240, 0.428
No. of measured, independent and
observed [I > 2σ(I)] reflections		14419, 3241, 2050
Rint0.121
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.169, 1.04
No. of reflections3241
No. of parameters196
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.54, −0.54

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H1O5···O2i0.872.312.736 (4)111
O5—H2O5···O2ii0.852.402.886 (4)117
Symmetry codes: (i) −x+1, −y−1, −z+2; (ii) x, −y−1/2, z+1/2.
 

References

First citationCaneschi, A., Chiesi, P., David, L., Ferraro, F., Gatteschi, D. & Sessoli, R. (1993). Inorg. Chem. 32, 1445–1453.  CrossRef CAS Google Scholar
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ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page m488
doi:10.1107/S1600536811009925
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