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

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ISSN: 2056-9890

Bis(μ-dithieno[3,2-b:2′,3′-d]thio­phene-2,6-di­carboxyl­ato-κ2O2:O6)bis­­[bis­­(1,10-phenanthroline-κ2N,N′)cobalt(II)] di­methyl­formamide disolvate

aDepartment of Chemistry, Wake Forest University, Winston-Salem, NC 27109, USA
*Correspondence e-mail: noftle@wfu.edu

(Received 29 January 2009; accepted 26 March 2009; online 8 April 2009)

The asymmetric unit of the title compound, [Co2(C10H2O4S3)2(C12H8N2)4]·2C3H7NO, contains one half of the formula unit, with the rest generated by inversion. The cobalt ion sits in a slightly distorted octa­hedral environment and is ligated to four N atoms of two 1,10-phenanthroline molecules and to two O atoms of two dithieno[3,2-b:2′,3′-d]thio­phene-2,6-dicarb­oxy­l­ate anions. The anions act as bridges between the CoII centers.

Related literature

For the synthesis of complexes with this ligand, see: Chisholm et al. (2008[Chisholm, M. H., Chou, P.-T., Chou, Y.-H., Ghosh, Y., Gustafson, T. L. & Ho, M.-L. (2008). Inorg. Chem. 47, 3415-3425.]). For similar complexes, see: Xiao et al. (2005[Xiao, H.-P., Hu, M.-L. & Yuan, J.-X. (2005). Acta Cryst. E61, m443-m445.]); Sun et al. (2005[Sun, Y.-G., Gao, E.-J., Wei, D.-Z. & Liu, Y.-N. (2005). Chin. J. Struct. Chem. 24, 1298-1301.]); Niu et al. (2004[Niu, S. Y., Jin, J. & Youy, Z. Z. (2004). Synth. React. Inorg. Met.-Org. Chem. 34, 173-185.]); Poleti et al. (1999[Poleti, D., Karanović, L., Bogdanović, G. A. & Spasojević-de Biré, A. (1999). Acta Cryst. C55, 2061-2063.]).

[Scheme 1]

Experimental

Crystal data
  • [Co2(C10H2O4S3)2(C12H8N2)4]·2C3H7NO

  • Mr = 1549.52

  • Triclinic, [P \overline 1]

  • a = 9.884 (3) Å

  • b = 11.492 (3) Å

  • c = 15.215 (4) Å

  • α = 91.173 (3)°

  • β = 105.065 (3)°

  • γ = 93.057 (3)°

  • V = 1665.4 (7) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.76 mm−1

  • T = 193 K

  • 0.12 × 0.10 × 0.04 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.828, Tmax = 0.970

  • 15360 measured reflections

  • 7532 independent reflections

  • 5496 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.133

  • S = 1.06

  • 7532 reflections

  • 462 parameters

  • H-atom parameters constrained

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

We obtained the title compound during the course of our studies while forming CoII/1,10 phen/DTTH based coordination polymers. The asymmetric unit of the compound contains one cobalt ion along with one DTTH molecule, two 1,10-phen molecules and one lattice dimethylformamide (DMF) solvent molecule. The dimer consists of two Co(1,10-phen)22+ cations linked by two bis-monodentate DTTH linkers. Each cobalt(II) ion is six-coordinate, forming a distorted octahedral geometry with the angles around Co1 ranging from 76.8 (1)°-104.1 (1)° and 163.9 (1)° -165.8 (1)°, respectively. Co1 is coordinated by four nitrogen atoms from two 1,10-phen moieties and two oxygen atoms from two bis-monodentate DTTH molecules. The Co—N bond lengths range from 2.127 (3)–2.192 (3)Å while the Co—O bond lengths range from 2.047 (2)–2.097 (2) Å. The angle between planes formed by the two 1,10-phen rings is 76.69 (6)°.

Related literature top

For the synthesis of complexes with this ligand, see: Chisholm et al. (2008). For similar complexes, see: Xiao et al. (2005); Sun et al. (2005); Niu et al. (2004); Poleti et al. (1999).

Experimental top

The title compound was prepared using a hydrothermal method. A mixture of cobalt nitrate pentahydrate (1.7 mmol), dithieno[3,2 - b:2',3'-d]thiophene-2,6-dicarboxylic acid (1.8 mmol) and 1,10-phenanthroline (5 mmol) were added to a vial containing DMF (1 ml) and EtOH (0.2 ml). The vial was capped and set in an oven at 105°C for 2 d. The vial was slowly cooled to room temperature to yield pink gem-like crystals.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008b); program(s) used to refine structure: SHELXTL (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top
[Figure 1] Fig. 1. A perspective drawing of the contents of the asymmetric unit for [Co(C12H8N2)2(C10H2O4S3)]2 -2 DMF. Non-hydrogen atoms are represented by 50% probability ellipsoids.
[Figure 2] Fig. 2. A perspective drawing of the dimeric unit for [Co(C12H8N2)2(C10H2O4S3)]2 -2 DMF. Cobalt and sulfur atoms are represented by large shaded and dotted spheres, oxygen and nitrogen atoms by medium-sized shaded spheres and carbon and hydrogen atoms by medium and small open spheres, respectively.
[Figure 3] Fig. 3. A projection down the a-axis of the unit cell in crystalline [Co(C12H8N2)2(C10H2O4S3)]2 – 2 DMF with atoms represented as in Figure 2. Hydrogen atoms have been omitted for clarity.
Bis(µ-dithieno[3,2-b:2',3'-d]thiophene-2,6-dicarboxylato- κ2O2:O6)bis[bis(1,10-phenanthroline- κ2N,N')cobalt(II)] dimethylformamide disolvate top
Crystal data top
[Co2(C10H2O4S3)2(C12H8N2)4]·2C3H7NOZ = 1
Mr = 1549.52F(000) = 794
Triclinic, P1Dx = 1.545 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.884 (3) ÅCell parameters from 2172 reflections
b = 11.492 (3) Åθ = 3.9–22.9°
c = 15.215 (4) ŵ = 0.76 mm1
α = 91.173 (3)°T = 193 K
β = 105.065 (3)°Gem, pink
γ = 93.057 (3)°0.12 × 0.10 × 0.04 mm
V = 1665.4 (7) Å3
Data collection top
Bruker APEX CCD
diffractometer
7532 independent reflections
Radiation source: fine-focus sealed tube5496 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ϕ and ω scansθmax = 27.5°, θmin = 3.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
h = 1212
Tmin = 0.828, Tmax = 0.970k = 1414
15360 measured reflectionsl = 1919
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.6813P]
where P = (Fo2 + 2Fc2)/3
7532 reflections(Δ/σ)max = 0.001
462 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Co2(C10H2O4S3)2(C12H8N2)4]·2C3H7NOγ = 93.057 (3)°
Mr = 1549.52V = 1665.4 (7) Å3
Triclinic, P1Z = 1
a = 9.884 (3) ÅMo Kα radiation
b = 11.492 (3) ŵ = 0.76 mm1
c = 15.215 (4) ÅT = 193 K
α = 91.173 (3)°0.12 × 0.10 × 0.04 mm
β = 105.065 (3)°
Data collection top
Bruker APEX CCD
diffractometer
7532 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
5496 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 0.970Rint = 0.045
15360 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.06Δρmax = 0.62 e Å3
7532 reflectionsΔρmin = 0.44 e Å3
462 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 > 2σ(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
Co10.34999 (5)0.24482 (4)0.79340 (3)0.02013 (13)
S10.04501 (10)0.25459 (8)0.52827 (6)0.0281 (2)
S20.25186 (10)0.02620 (8)0.60913 (6)0.0299 (2)
S30.14365 (9)0.13442 (8)0.34898 (6)0.0240 (2)
O10.1611 (2)0.2315 (2)0.75483 (15)0.0264 (6)
O20.2189 (3)0.3579 (3)0.63494 (19)0.0516 (9)
O30.2470 (3)0.0587 (2)0.19493 (16)0.0291 (6)
O40.3956 (2)0.0885 (2)0.26610 (16)0.0257 (5)
N10.5146 (3)0.2245 (3)0.86423 (19)0.0248 (6)
N20.2355 (3)0.1859 (2)0.92703 (18)0.0238 (6)
N30.4950 (3)0.3311 (2)0.67959 (19)0.0227 (6)
N40.3249 (3)0.4266 (3)0.82227 (19)0.0249 (6)
C10.1500 (4)0.2735 (3)0.6790 (2)0.0279 (8)
C20.0441 (4)0.2122 (3)0.6389 (2)0.0239 (7)
C30.0813 (3)0.1463 (3)0.5260 (2)0.0233 (7)
C40.1506 (3)0.1030 (3)0.4618 (2)0.0217 (7)
C50.2701 (3)0.0221 (3)0.3501 (2)0.0223 (7)
C60.3144 (4)0.0356 (3)0.4327 (2)0.0256 (8)
H60.38290.09920.44580.031*
C70.2462 (4)0.0108 (3)0.4965 (2)0.0247 (8)
C80.1232 (4)0.0842 (3)0.6088 (2)0.0238 (7)
C90.0504 (4)0.1213 (3)0.6728 (2)0.0246 (8)
H90.06550.08700.73210.030*
C100.3060 (4)0.0040 (3)0.2626 (2)0.0222 (7)
C110.6518 (4)0.2416 (3)0.8323 (3)0.0340 (9)
H110.68810.27190.77170.041*
C120.7471 (4)0.2171 (4)0.8838 (3)0.0442 (11)
H120.84530.23140.85880.053*
C130.6955 (4)0.1725 (4)0.9702 (3)0.0467 (11)
H130.75850.15411.00540.056*
C140.5511 (4)0.1535 (4)1.0079 (3)0.0367 (10)
C150.4884 (5)0.1077 (4)1.0981 (3)0.0436 (11)
H150.54700.08601.13550.052*
C160.3495 (5)0.0947 (4)1.1308 (3)0.0426 (11)
H160.31120.06721.19200.051*
C170.2559 (4)0.1213 (3)1.0757 (2)0.0293 (8)
C180.1105 (4)0.1083 (4)1.1059 (3)0.0380 (10)
H180.06640.08321.16700.046*
C190.0319 (4)0.1316 (4)1.0472 (3)0.0466 (11)
H190.06760.12201.06690.056*
C200.0977 (4)0.1699 (4)0.9581 (3)0.0387 (10)
H200.04110.18510.91790.046*
C210.3148 (4)0.1624 (3)0.9851 (2)0.0227 (7)
C220.4630 (4)0.1814 (3)0.9514 (2)0.0260 (8)
C230.5794 (4)0.2829 (3)0.6092 (2)0.0286 (8)
H230.58390.20050.61010.034*
C240.6620 (4)0.3476 (3)0.5338 (3)0.0336 (9)
H240.72000.30930.48450.040*
C250.6588 (4)0.4672 (3)0.5312 (3)0.0334 (9)
H250.71510.51240.48060.040*
C260.5707 (4)0.5212 (3)0.6049 (2)0.0280 (8)
C270.5593 (4)0.6450 (3)0.6079 (3)0.0334 (9)
H270.61450.69430.55940.040*
C280.4704 (4)0.6915 (3)0.6793 (3)0.0372 (9)
H280.46300.77360.67980.045*
C290.3870 (4)0.6208 (3)0.7541 (3)0.0304 (8)
C300.2932 (5)0.6661 (4)0.8302 (3)0.0419 (10)
H300.28060.74740.83340.050*
C310.2213 (5)0.5919 (4)0.8988 (3)0.0447 (11)
H310.15830.62110.95070.054*
C320.2397 (4)0.4726 (3)0.8932 (3)0.0338 (9)
H320.18900.42220.94240.041*
C330.3986 (3)0.5003 (3)0.7537 (2)0.0238 (7)
C340.4911 (3)0.4491 (3)0.6776 (2)0.0233 (7)
O50.0843 (5)0.5229 (5)1.1015 (3)0.1188 (19)
N50.1221 (5)0.4568 (4)1.2325 (3)0.0676 (13)
C350.0501 (6)0.5057 (5)1.1833 (4)0.0686 (16)
H350.03900.53081.21490.082*
C360.0661 (9)0.4434 (7)1.3303 (5)0.124 (3)
H36A0.03190.46431.34710.186*
H36B0.12120.49461.36040.186*
H36C0.07120.36221.34950.186*
C370.2573 (9)0.4182 (8)1.1872 (7)0.170 (5)
H37A0.26570.41501.12170.255*
H37B0.26790.34041.21120.255*
H37C0.33070.47271.19760.255*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0232 (2)0.0210 (2)0.0178 (2)0.00021 (18)0.00842 (19)0.00068 (18)
S10.0325 (5)0.0338 (5)0.0213 (4)0.0060 (4)0.0147 (4)0.0054 (4)
S20.0367 (5)0.0334 (5)0.0198 (4)0.0072 (4)0.0100 (4)0.0036 (4)
S30.0295 (5)0.0259 (5)0.0189 (4)0.0025 (4)0.0112 (4)0.0011 (3)
O10.0304 (14)0.0321 (14)0.0205 (12)0.0009 (11)0.0143 (10)0.0038 (10)
O20.0568 (19)0.061 (2)0.0436 (17)0.0321 (16)0.0342 (15)0.0298 (15)
O30.0367 (15)0.0282 (14)0.0248 (13)0.0034 (11)0.0138 (11)0.0016 (11)
O40.0277 (13)0.0236 (13)0.0267 (13)0.0027 (10)0.0100 (11)0.0006 (10)
N10.0247 (16)0.0279 (16)0.0238 (15)0.0022 (13)0.0097 (12)0.0041 (13)
N20.0271 (16)0.0276 (16)0.0195 (14)0.0024 (13)0.0110 (12)0.0021 (12)
N30.0243 (15)0.0230 (15)0.0233 (15)0.0036 (12)0.0099 (12)0.0011 (12)
N40.0266 (16)0.0265 (16)0.0220 (15)0.0010 (13)0.0074 (13)0.0016 (12)
C10.0288 (19)0.033 (2)0.0245 (18)0.0010 (16)0.0126 (15)0.0031 (16)
C20.0273 (19)0.0296 (19)0.0173 (17)0.0050 (15)0.0099 (14)0.0002 (14)
C30.0249 (18)0.0282 (19)0.0182 (17)0.0029 (15)0.0080 (14)0.0008 (14)
C40.0257 (18)0.0251 (18)0.0160 (16)0.0022 (14)0.0083 (14)0.0010 (14)
C50.0243 (18)0.0214 (18)0.0236 (18)0.0006 (14)0.0106 (14)0.0033 (14)
C60.0278 (19)0.0266 (19)0.0241 (18)0.0002 (15)0.0102 (15)0.0007 (15)
C70.0301 (19)0.0272 (19)0.0171 (17)0.0013 (15)0.0068 (15)0.0013 (14)
C80.0265 (18)0.0259 (19)0.0209 (17)0.0024 (15)0.0094 (14)0.0006 (14)
C90.0304 (19)0.029 (2)0.0172 (17)0.0053 (15)0.0101 (15)0.0002 (14)
C100.0259 (18)0.0206 (18)0.0224 (17)0.0062 (14)0.0096 (14)0.0022 (14)
C110.028 (2)0.043 (2)0.032 (2)0.0019 (17)0.0105 (17)0.0071 (18)
C120.023 (2)0.066 (3)0.050 (3)0.005 (2)0.0181 (19)0.015 (2)
C130.041 (3)0.067 (3)0.043 (3)0.014 (2)0.029 (2)0.015 (2)
C140.038 (2)0.049 (3)0.032 (2)0.0103 (19)0.0219 (18)0.0091 (19)
C150.050 (3)0.058 (3)0.034 (2)0.013 (2)0.029 (2)0.001 (2)
C160.061 (3)0.052 (3)0.021 (2)0.007 (2)0.022 (2)0.0047 (19)
C170.041 (2)0.029 (2)0.0204 (18)0.0060 (17)0.0119 (16)0.0000 (15)
C180.044 (2)0.047 (3)0.0199 (19)0.000 (2)0.0032 (17)0.0091 (17)
C190.028 (2)0.069 (3)0.038 (2)0.000 (2)0.0030 (18)0.015 (2)
C200.026 (2)0.062 (3)0.029 (2)0.0007 (19)0.0116 (17)0.0158 (19)
C210.0307 (19)0.0239 (18)0.0172 (16)0.0051 (15)0.0122 (14)0.0034 (14)
C220.036 (2)0.0265 (19)0.0222 (18)0.0059 (16)0.0177 (16)0.0047 (15)
C230.027 (2)0.031 (2)0.0272 (19)0.0044 (16)0.0061 (16)0.0001 (16)
C240.031 (2)0.041 (2)0.027 (2)0.0062 (17)0.0031 (16)0.0017 (17)
C250.029 (2)0.040 (2)0.028 (2)0.0009 (17)0.0030 (16)0.0128 (17)
C260.0243 (19)0.030 (2)0.030 (2)0.0011 (15)0.0083 (16)0.0049 (16)
C270.033 (2)0.029 (2)0.037 (2)0.0042 (17)0.0096 (18)0.0117 (17)
C280.042 (2)0.023 (2)0.047 (3)0.0001 (17)0.015 (2)0.0041 (18)
C290.035 (2)0.0230 (19)0.035 (2)0.0001 (16)0.0111 (17)0.0020 (16)
C300.051 (3)0.026 (2)0.046 (3)0.0064 (19)0.006 (2)0.0097 (19)
C310.052 (3)0.034 (2)0.041 (2)0.010 (2)0.004 (2)0.0101 (19)
C320.039 (2)0.033 (2)0.026 (2)0.0019 (18)0.0020 (17)0.0033 (17)
C330.0207 (17)0.0244 (19)0.0270 (18)0.0025 (14)0.0086 (14)0.0006 (15)
C340.0222 (18)0.0282 (19)0.0221 (18)0.0018 (14)0.0102 (14)0.0005 (15)
O50.089 (3)0.206 (6)0.052 (3)0.016 (3)0.009 (2)0.025 (3)
N50.074 (3)0.068 (3)0.079 (3)0.007 (2)0.051 (3)0.009 (3)
C350.058 (3)0.099 (5)0.047 (3)0.001 (3)0.013 (3)0.003 (3)
C360.173 (8)0.134 (7)0.085 (5)0.032 (6)0.080 (5)0.041 (5)
C370.134 (7)0.193 (10)0.247 (11)0.103 (7)0.136 (8)0.151 (9)
Geometric parameters (Å, º) top
Co1—O4i2.047 (2)C15—C161.332 (6)
Co1—O12.097 (2)C15—H150.9500
Co1—N32.127 (3)C16—C171.440 (5)
Co1—N22.130 (3)C16—H160.9500
Co1—N42.158 (3)C17—C181.389 (5)
Co1—N12.192 (3)C17—C211.411 (5)
S1—C31.722 (3)C18—C191.359 (6)
S1—C21.740 (3)C18—H180.9500
S2—C71.743 (3)C19—C201.393 (5)
S2—C81.747 (4)C19—H190.9500
S3—C41.730 (3)C20—H200.9500
S3—C51.744 (3)C21—C221.424 (5)
O1—C11.274 (4)C23—C241.396 (5)
O2—C11.233 (4)C23—H230.9500
O3—C101.238 (4)C24—C251.376 (5)
O4—C101.270 (4)C24—H240.9500
O4—Co1i2.047 (2)C25—C261.407 (5)
N1—C111.319 (5)C25—H250.9500
N1—C221.363 (4)C26—C341.403 (5)
N2—C201.322 (5)C26—C271.434 (5)
N2—C211.356 (4)C27—C281.347 (6)
N3—C231.327 (4)C27—H270.9500
N3—C341.359 (4)C28—C291.428 (5)
N4—C321.323 (5)C28—H280.9500
N4—C331.356 (4)C29—C331.395 (5)
C1—C21.496 (5)C29—C301.411 (5)
C2—C91.361 (5)C30—C311.354 (6)
C3—C81.390 (4)C30—H300.9500
C3—C41.415 (4)C31—C321.394 (5)
C4—C71.380 (5)C31—H310.9500
C5—C61.363 (5)C32—H320.9500
C5—C101.496 (4)C33—C341.435 (5)
C6—C71.415 (5)O5—C351.212 (6)
C6—H60.9500N5—C351.297 (6)
C8—C91.412 (4)N5—C371.434 (9)
C9—H90.9500N5—C361.448 (8)
C11—C121.409 (5)C35—H350.9500
C11—H110.9500C36—H36A0.9800
C12—C131.358 (6)C36—H36B0.9800
C12—H120.9500C36—H36C0.9800
C13—C141.397 (6)C37—H37A0.9800
C13—H130.9500C37—H37B0.9800
C14—C221.417 (5)C37—H37C0.9800
C14—C151.427 (6)
O4i—Co1—O187.55 (9)C14—C15—H15119.3
O4i—Co1—N389.33 (10)C15—C16—C17121.6 (4)
O1—Co1—N3104.10 (10)C15—C16—H16119.2
O4i—Co1—N2100.37 (10)C17—C16—H16119.2
O1—Co1—N288.27 (10)C18—C17—C21117.5 (3)
N3—Co1—N2164.68 (11)C18—C17—C16124.2 (4)
O4i—Co1—N4165.78 (10)C21—C17—C16118.3 (4)
O1—Co1—N491.40 (10)C19—C18—C17119.5 (4)
N3—Co1—N477.16 (11)C19—C18—H18120.3
N2—Co1—N493.77 (11)C17—C18—H18120.3
O4i—Co1—N189.40 (10)C18—C19—C20119.7 (4)
O1—Co1—N1163.91 (10)C18—C19—H19120.1
N3—Co1—N191.65 (11)C20—C19—H19120.1
N2—Co1—N176.75 (11)N2—C20—C19122.9 (3)
N4—Co1—N195.35 (11)N2—C20—H20118.5
C3—S1—C291.21 (16)C19—C20—H20118.5
C7—S2—C890.49 (16)N2—C21—C17122.7 (3)
C4—S3—C590.95 (16)N2—C21—C22117.4 (3)
C1—O1—Co1122.3 (2)C17—C21—C22120.0 (3)
C10—O4—Co1i124.4 (2)N1—C22—C14122.5 (3)
C11—N1—C22118.2 (3)N1—C22—C21117.8 (3)
C11—N1—Co1129.0 (2)C14—C22—C21119.7 (3)
C22—N1—Co1112.7 (2)N3—C23—C24123.1 (4)
C20—N2—C21117.7 (3)N3—C23—H23118.5
C20—N2—Co1127.0 (2)C24—C23—H23118.5
C21—N2—Co1115.3 (2)C25—C24—C23119.7 (4)
C23—N3—C34117.7 (3)C25—C24—H24120.2
C23—N3—Co1127.6 (2)C23—C24—H24120.2
C34—N3—Co1114.5 (2)C24—C25—C26118.8 (3)
C32—N4—C33117.7 (3)C24—C25—H25120.6
C32—N4—Co1128.3 (3)C26—C25—H25120.6
C33—N4—Co1113.7 (2)C34—C26—C25117.6 (3)
O2—C1—O1126.8 (3)C34—C26—C27119.7 (3)
O2—C1—C2116.9 (3)C25—C26—C27122.8 (3)
O1—C1—C2116.3 (3)C28—C27—C26120.1 (4)
C9—C2—C1130.4 (3)C28—C27—H27120.0
C9—C2—S1112.5 (2)C26—C27—H27120.0
C1—C2—S1116.9 (2)C27—C28—C29121.8 (4)
C8—C3—C4112.3 (3)C27—C28—H28119.1
C8—C3—S1110.8 (2)C29—C28—H28119.1
C4—C3—S1136.9 (3)C33—C29—C30117.3 (3)
C7—C4—C3112.8 (3)C33—C29—C28119.2 (3)
C7—C4—S3111.1 (2)C30—C29—C28123.6 (4)
C3—C4—S3136.1 (3)C31—C30—C29119.0 (4)
C6—C5—C10129.3 (3)C31—C30—H30120.5
C6—C5—S3112.4 (2)C29—C30—H30120.5
C10—C5—S3118.1 (2)C30—C31—C32120.0 (4)
C5—C6—C7111.8 (3)C30—C31—H31120.0
C5—C6—H6124.1C32—C31—H31120.0
C7—C6—H6124.1N4—C32—C31122.7 (4)
C4—C7—C6113.7 (3)N4—C32—H32118.6
C4—C7—S2112.3 (2)C31—C32—H32118.6
C6—C7—S2134.0 (3)N4—C33—C29123.2 (3)
C3—C8—C9113.7 (3)N4—C33—C34117.0 (3)
C3—C8—S2112.1 (2)C29—C33—C34119.8 (3)
C9—C8—S2134.2 (3)N3—C34—C26123.3 (3)
C2—C9—C8111.7 (3)N3—C34—C33117.2 (3)
C2—C9—H9124.1C26—C34—C33119.5 (3)
C8—C9—H9124.1C35—N5—C37118.1 (6)
O3—C10—O4126.7 (3)C35—N5—C36120.1 (6)
O3—C10—C5117.4 (3)C37—N5—C36121.8 (6)
O4—C10—C5115.9 (3)O5—C35—N5127.0 (6)
N1—C11—C12123.1 (4)O5—C35—H35116.5
N1—C11—H11118.4N5—C35—H35116.5
C12—C11—H11118.4N5—C36—H36A109.5
C13—C12—C11118.5 (4)N5—C36—H36B109.5
C13—C12—H12120.7H36A—C36—H36B109.5
C11—C12—H12120.7N5—C36—H36C109.5
C12—C13—C14120.9 (4)H36A—C36—H36C109.5
C12—C13—H13119.6H36B—C36—H36C109.5
C14—C13—H13119.6N5—C37—H37A109.5
C13—C14—C22116.7 (4)N5—C37—H37B109.5
C13—C14—C15124.4 (4)H37A—C37—H37B109.5
C22—C14—C15118.9 (4)N5—C37—H37C109.5
C16—C15—C14121.4 (4)H37A—C37—H37C109.5
C16—C15—H15119.3H37B—C37—H37C109.5
O4i—Co1—O1—C190.8 (3)Co1i—O4—C10—O370.5 (4)
N3—Co1—O1—C12.1 (3)Co1i—O4—C10—C5110.2 (3)
N2—Co1—O1—C1168.8 (3)C6—C5—C10—O3176.8 (3)
N4—Co1—O1—C175.0 (3)S3—C5—C10—O32.5 (4)
N1—Co1—O1—C1170.0 (4)C6—C5—C10—O43.7 (5)
O4i—Co1—N1—C1177.8 (3)S3—C5—C10—O4178.1 (2)
O1—Co1—N1—C11156.8 (4)C22—N1—C11—C120.2 (6)
N3—Co1—N1—C1111.5 (3)Co1—N1—C11—C12175.2 (3)
N2—Co1—N1—C11178.6 (3)N1—C11—C12—C130.7 (6)
N4—Co1—N1—C1188.8 (3)C11—C12—C13—C141.3 (7)
O4i—Co1—N1—C2297.9 (2)C12—C13—C14—C220.9 (6)
O1—Co1—N1—C2218.9 (5)C12—C13—C14—C15179.7 (4)
N3—Co1—N1—C22172.8 (2)C13—C14—C15—C16178.1 (4)
N2—Co1—N1—C222.9 (2)C22—C14—C15—C162.4 (6)
N4—Co1—N1—C2295.5 (2)C14—C15—C16—C172.8 (7)
O4i—Co1—N2—C2094.9 (3)C15—C16—C17—C18179.3 (4)
O1—Co1—N2—C207.7 (3)C15—C16—C17—C210.2 (6)
N3—Co1—N2—C20136.6 (4)C21—C17—C18—C192.1 (6)
N4—Co1—N2—C2083.6 (3)C16—C17—C18—C19177.5 (4)
N1—Co1—N2—C20178.2 (4)C17—C18—C19—C200.9 (7)
O4i—Co1—N2—C2184.7 (2)C21—N2—C20—C190.8 (6)
O1—Co1—N2—C21171.9 (2)Co1—N2—C20—C19179.6 (3)
N3—Co1—N2—C2143.8 (5)C18—C19—C20—N20.6 (7)
N4—Co1—N2—C2196.8 (2)C20—N2—C21—C170.5 (5)
N1—Co1—N2—C212.2 (2)Co1—N2—C21—C17179.2 (3)
O4i—Co1—N3—C234.7 (3)C20—N2—C21—C22179.2 (3)
O1—Co1—N3—C2392.0 (3)Co1—N2—C21—C221.1 (4)
N2—Co1—N3—C23124.9 (4)C18—C17—C21—N21.9 (5)
N4—Co1—N3—C23179.7 (3)C16—C17—C21—N2177.7 (3)
N1—Co1—N3—C2384.6 (3)C18—C17—C21—C22177.8 (3)
O4i—Co1—N3—C34170.2 (2)C16—C17—C21—C222.7 (5)
O1—Co1—N3—C3482.9 (2)C11—N1—C22—C140.7 (5)
N2—Co1—N3—C3460.1 (5)Co1—N1—C22—C14175.5 (3)
N4—Co1—N3—C345.3 (2)C11—N1—C22—C21179.5 (3)
N1—Co1—N3—C34100.4 (2)Co1—N1—C22—C213.4 (4)
O4i—Co1—N4—C32161.2 (4)C13—C14—C22—N10.1 (6)
O1—Co1—N4—C3275.6 (3)C15—C14—C22—N1179.4 (3)
N3—Co1—N4—C32179.7 (3)C13—C14—C22—C21179.0 (4)
N2—Co1—N4—C3212.8 (3)C15—C14—C22—C210.5 (6)
N1—Co1—N4—C3289.8 (3)N2—C21—C22—N11.6 (5)
O4i—Co1—N4—C3312.6 (5)C17—C21—C22—N1178.1 (3)
O1—Co1—N4—C3398.2 (2)N2—C21—C22—C14177.3 (3)
N3—Co1—N4—C335.9 (2)C17—C21—C22—C143.0 (5)
N2—Co1—N4—C33173.4 (2)C34—N3—C23—C240.7 (5)
N1—Co1—N4—C3396.4 (2)Co1—N3—C23—C24174.1 (3)
Co1—O1—C1—O228.4 (5)N3—C23—C24—C250.8 (6)
Co1—O1—C1—C2150.4 (2)C23—C24—C25—C260.6 (5)
O2—C1—C2—C9176.7 (4)C24—C25—C26—C340.4 (5)
O1—C1—C2—C94.4 (6)C24—C25—C26—C27179.3 (3)
O2—C1—C2—S18.0 (5)C34—C26—C27—C281.4 (5)
O1—C1—C2—S1170.9 (3)C25—C26—C27—C28178.3 (4)
C3—S1—C2—C91.2 (3)C26—C27—C28—C290.9 (6)
C3—S1—C2—C1174.9 (3)C27—C28—C29—C330.5 (6)
C2—S1—C3—C81.8 (3)C27—C28—C29—C30179.7 (4)
C2—S1—C3—C4176.5 (4)C33—C29—C30—C310.8 (6)
C8—C3—C4—C71.4 (4)C28—C29—C30—C31178.4 (4)
S1—C3—C4—C7179.6 (3)C29—C30—C31—C320.5 (7)
C8—C3—C4—S3177.0 (3)C33—N4—C32—C311.4 (6)
S1—C3—C4—S31.2 (6)Co1—N4—C32—C31172.2 (3)
C5—S3—C4—C70.1 (3)C30—C31—C32—N40.7 (7)
C5—S3—C4—C3178.4 (4)C32—N4—C33—C291.0 (5)
C4—S3—C5—C60.0 (3)Co1—N4—C33—C29173.5 (3)
C4—S3—C5—C10175.2 (3)C32—N4—C33—C34179.6 (3)
C10—C5—C6—C7174.6 (3)Co1—N4—C33—C345.9 (4)
S3—C5—C6—C70.0 (4)C30—C29—C33—N40.1 (5)
C3—C4—C7—C6178.7 (3)C28—C29—C33—N4179.2 (3)
S3—C4—C7—C60.1 (4)C30—C29—C33—C34179.3 (3)
C3—C4—C7—S20.7 (4)C28—C29—C33—C341.5 (5)
S3—C4—C7—S2178.14 (18)C23—N3—C34—C260.5 (5)
C5—C6—C7—C40.1 (5)Co1—N3—C34—C26175.0 (3)
C5—C6—C7—S2177.5 (3)C23—N3—C34—C33179.5 (3)
C8—S2—C7—C40.1 (3)Co1—N3—C34—C334.0 (4)
C8—S2—C7—C6177.4 (4)C25—C26—C34—N30.3 (5)
C4—C3—C8—C9176.7 (3)C27—C26—C34—N3179.4 (3)
S1—C3—C8—C92.0 (4)C25—C26—C34—C33179.3 (3)
C4—C3—C8—S21.5 (4)C27—C26—C34—C330.4 (5)
S1—C3—C8—S2179.82 (18)N4—C33—C34—N31.3 (4)
C7—S2—C8—C30.9 (3)C29—C33—C34—N3178.0 (3)
C7—S2—C8—C9176.8 (4)N4—C33—C34—C26179.6 (3)
C1—C2—C9—C8175.2 (4)C29—C33—C34—C261.0 (5)
S1—C2—C9—C80.3 (4)C37—N5—C35—O50.1 (10)
C3—C8—C9—C21.1 (4)C36—N5—C35—O5179.7 (6)
S2—C8—C9—C2178.8 (3)
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Co2(C10H2O4S3)2(C12H8N2)4]·2C3H7NO
Mr1549.52
Crystal system, space groupTriclinic, P1
Temperature (K)193
a, b, c (Å)9.884 (3), 11.492 (3), 15.215 (4)
α, β, γ (°)91.173 (3), 105.065 (3), 93.057 (3)
V3)1665.4 (7)
Z1
Radiation typeMo Kα
µ (mm1)0.76
Crystal size (mm)0.12 × 0.10 × 0.04
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008a)
Tmin, Tmax0.828, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
15360, 7532, 5496
Rint0.045
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.133, 1.06
No. of reflections7532
No. of parameters462
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.62, 0.44

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2008b).

 

Acknowledgements

The authors thank the National Science Foundation (grant CHE-0234489) for funds to purchase the X-ray instrument and computers. We also thank the Wake Forest University Science Research Fund for the partial support of this project.

References

First citationBruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChisholm, M. H., Chou, P.-T., Chou, Y.-H., Ghosh, Y., Gustafson, T. L. & Ho, M.-L. (2008). Inorg. Chem. 47, 3415-3425.  Web of Science CrossRef PubMed CAS Google Scholar
First citationNiu, S. Y., Jin, J. & Youy, Z. Z. (2004). Synth. React. Inorg. Met.-Org. Chem. 34, 173–185.  Web of Science CSD CrossRef CAS Google Scholar
First citationPoleti, D., Karanović, L., Bogdanović, G. A. & Spasojević-de Biré, A. (1999). Acta Cryst. C55, 2061–2063.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, Y.-G., Gao, E.-J., Wei, D.-Z. & Liu, Y.-N. (2005). Chin. J. Struct. Chem. 24, 1298–1301.  CAS Google Scholar
First citationXiao, H.-P., Hu, M.-L. & Yuan, J.-X. (2005). Acta Cryst. E61, m443–m445.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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