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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m673–m674.
Published online 2010 May 19. doi:  10.1107/S1600536810017435
PMCID: PMC2979455

Bis(2,2′-bipyridyl dioxide-κ2 N,N′)bis­(tricyano­methanido)cobalt(II) dihydrate

Abstract

In the title compound, [Co(C4N3)2(C10H8N2O2)]·2H2O, a novel tricyano­methanide complex, the CoII atom is located on an inversion center and has a distorted octa­hedral coordination with two 2,2′-bipyridyl dioxide (dpdo) mol­ecules and two trans tricyano­methanide (tcm) anions. The equatorial plane is formed by the four O atoms of the two chelating dpdo ligands, with one N atom of each of the two tcm ligands occupying an apical position. There is a disordered solvent water mol­ecule in the asymmetric unit (occupancy ratio 0.63:0.37). These water mol­ecules result in the formation of O—H(...)O and O—H(...)N hydrogen bonds, building a layer parallel to (100). The layers are linked by C—H(...)N hydrogen-bonding inter­actions, leading to a three-dimensional network.

Related literature

For coordination polymers constructed with tricyano­methanide, see: Abrahams et al. (2003 [triangle]); Batten & Murray (2003 [triangle]); Batten et al. (1998 [triangle], 1999 [triangle], 2000 [triangle]); Feyerherm et al. (2003 [triangle], 2004 [triangle]); Hoshino et al. (1999 [triangle]); Manson & Schlueter (2004 [triangle]); Manson et al. (1998 [triangle], 2000 [triangle]); Miller & Manson (2001 [triangle]); Yuste et al. (2007 [triangle], 2008 [triangle]). For complexes containing dpdo, see: Luo et al. (2009 [triangle]); Zhang et al. (2010 [triangle]); Su & Lan (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m673-scheme1.jpg

Experimental

Crystal data

  • [Co(C4N3)2(C10H8N2O2)]·2H2O
  • M r = 651.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m673-efi1.jpg
  • a = 9.575 (3) Å
  • b = 16.699 (6) Å
  • c = 9.442 (3) Å
  • β = 95.307 (4)°
  • V = 1503.3 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.63 mm−1
  • T = 293 K
  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.911, T max = 0.940
  • 7102 measured reflections
  • 3193 independent reflections
  • 2511 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.084
  • S = 0.99
  • 3193 reflections
  • 214 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]), ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017435/dn2560sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017435/dn2560Isup2.hkl

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

Acknowledgments

This project was supported by the National Natural Science Foundation of China (20571086).

supplementary crystallographic information

Comment

Coordination polymers constructed by tricyanomethanide (tcm) have attracted considerable interest due to their diverse structures and fascinating magnetic properties (Batten et al., 2003; Miller et al., 2001; Feyerherm et al., 2003). Notably, except a doubly interpenetrated (6,3) sheet was observed in Ag(tcm)2 (Abrahams et al., 2003), most binary tcm complexes display a rutile-like structure (Manson et al., 2000, 1998; Hoshino et al., 1999; Feyerherm et al., 2004). To gain insight into the influence of the co-ligands on the structures and magnetic properties of tcm complexes, some co-ligands such as hexamethyl-enetetramine, 4,4-bipyridyl, 1,2-bi(4-pyridyl)ethane were introduced to the binary tcm systems. Among the Cu(I) or Cd(II) tcm complexes with these co-ligands, numerous structure types range from doubly interpenetrated (4,4) sheet to 3D rutile networks were observed (Batten et al., 2000, 1998). By contrast, modification of the Mn(II)-tcm binary system with 4,4-bipyridyl as co-ligands leads to the formation of a one dimensional chain-like structure (Manson et al., 2004). Recently, several copper tcm complexes with nitrogen-containing heterocyclic co-ligands has been characterized (Yuste et al., 2008, 2007). On the other hand, 2,2'-dipyridyl N,N'-dioxide (dpdo) is a new co-ligand and has two potential oxygen donor atoms, however, few tcm complex with dpdo co-ligand has been reported (Luo et al., 2009). During our systematic investigation of the nature of dpdo co-ligand on the structures and properties of tcm complexes, we obtained a new tcm complex Co(dpdo)2(C4N3)2(H2O)2 (I), we herein report the synthesis and crystal structure of the complex.

In the title compound, the cobalt atom, located on an inversion center, has a distorted octahedral geometry with two dpdo molecules and two trans tricyanomethanide. The equatorial plane being formed by the four O atoms of the two chelating dpdo ligands whereas one N atom of each tcm ligands occupying the apical positions (Fig. 1).

Interestingly, two solvate water molecules are observed and the situation is different from the similar manganese complex reported in which no water molecules were found (Luo et al., 2009). In the title compound, these water molecules result in the formation of O-H···O and O-H···N hydrogen bonds building a layer parallel to the (1 0 0) plane (Table 1, Fig. 2). Furthermore, C-H···N hydrogen interactions (Table 1) link these layers forming a three dimensionnal network.

The Co—O(dpdo) distances are in the range 2.050 (1)Å - 2.070 (1) Å, these values are comparable to the corresponding distances in cobalt- nitroxide complexes (Zhang et al., 2010) and in the Co(dpdo)2(H2O)2 (Su & Lan, 2007). The Co—N(tcm) distances are 2.110 (2) Å, and the data are similar to the corresponding distances observed in cobalt tcm complex (Batten et al., 1999).

Each tricyanomethanide moiety is almost planar. Bond distances and bond angles within the anions are in good agreement with those found in other tricyanomethanide complexes (Hoshino et al., 1999; Batten et al., 1999).

Experimental

A 5 ml warm acetonitrile solution of 2,2'-dipyridyl N,N'-dioxide (0.10 mmol, 18.82 mg) and a 2 ml aqueous red solution of cobalt nitrate (0.10 mmol, 29.10 mg) were mixed and stirred for 5 min s, the mixed solution was orange. To the mixture was added a 3 ml acetonitrile-water solution (CH3CN:H2O = 2:1, V:V) of potassium tricyanomethanide (0.20 mmol, 25.83 mg). After stirred for another 5 min s, the orange solution was filtered and the filtrate was slowly evaporated in air. After two weeks, orange block crystals of I were isolated in 34% yield.

Anal: Calculated for C28H20CoN10O6: C 51.62%, H 3.10%, N 21.50%. Found C 51.77%, H 3.19%, N 21.64%.

Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å with Uiso(H) = 1.2Ueq(C). H atoms of water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O-H= 0.85 (1)Å and H···H= 1.39 (2)Å) with Uiso(H) = 1.5Ueq(O). In the last stage of refinement, they were treated as riding on the O atom.

The water molecules appear to be disorered over two positions with occupancy factors roughly in the ratio 2/1. The occupancy factors were determined using a constrained refinement with the sum of the occupancy fixed to 1.

Figures

Fig. 1.
A view of the mononuclear structure in (I), showing the atom- labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity [symmetry code: (i) -x+1, -y+1,-z+1].
Fig. 2.
Partial packing view along the a axis showing the three dimensional structure formed through O-H···O, O-H···N and C-H···N hydrogen bondings. H atoms not involved in hydrogen bondings ...

Crystal data

[Co(C4N3)2(C10H8N2O2)]·2H2OF(000) = 666
Mr = 651.47Dx = 1.439 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 887 reflections
a = 9.575 (3) Åθ = 2.5–26.6°
b = 16.699 (6) ŵ = 0.63 mm1
c = 9.442 (3) ÅT = 293 K
β = 95.307 (4)°Block, orange
V = 1503.3 (9) Å30.15 × 0.12 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer3193 independent reflections
Radiation source: fine-focus sealed tube2511 reflections with I > 2σ(I)
graphiteRint = 0.026
phi and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −12→7
Tmin = 0.911, Tmax = 0.940k = −20→18
7102 measured reflectionsl = −8→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3
3193 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/UeqOcc. (<1)
Co10.50000.50000.50000.03207 (11)
O10.63648 (11)0.55420 (6)0.37193 (12)0.0390 (3)
O20.60938 (11)0.55988 (6)0.66433 (12)0.0390 (3)
N10.64813 (13)0.63342 (7)0.38754 (14)0.0361 (3)
N20.74874 (13)0.55615 (7)0.67045 (14)0.0371 (3)
N30.36144 (13)0.59847 (8)0.48907 (16)0.0451 (4)
N40.3061 (2)0.85771 (11)0.5359 (3)0.0933 (7)
N50.0012 (2)0.71277 (15)0.2587 (3)0.1017 (8)
C10.57248 (18)0.68142 (10)0.29627 (19)0.0447 (4)
H10.51310.65950.22290.054*
C20.5829 (2)0.76308 (11)0.3113 (2)0.0519 (5)
H20.52950.79640.24870.062*
C30.6710 (2)0.79551 (10)0.4175 (2)0.0524 (5)
H30.67800.85080.42830.063*
C40.74983 (19)0.74506 (10)0.5088 (2)0.0476 (4)
H40.81230.76640.58020.057*
C50.73654 (16)0.66330 (9)0.49468 (18)0.0374 (4)
C60.81807 (16)0.60621 (9)0.58911 (18)0.0394 (4)
C70.96264 (18)0.60478 (12)0.6027 (2)0.0591 (5)
H71.01180.63990.54930.071*
C81.0347 (2)0.55240 (13)0.6937 (3)0.0707 (6)
H81.13230.55150.70190.085*
C90.9616 (2)0.50173 (12)0.7720 (3)0.0643 (6)
H91.00920.46530.83330.077*
C100.8172 (2)0.50427 (9)0.7606 (2)0.0494 (5)
H100.76730.47010.81530.059*
C110.29971 (16)0.65579 (10)0.45990 (19)0.0400 (4)
C120.22334 (18)0.72533 (10)0.4249 (2)0.0471 (4)
C130.2679 (2)0.79855 (12)0.4860 (3)0.0598 (5)
C140.1018 (2)0.71979 (11)0.3308 (2)0.0607 (5)
O30.6888 (5)0.5258 (4)0.0838 (8)0.0781 (13)0.63
H3A0.67970.47490.07800.117*0.63
H3B0.67150.53850.16850.117*0.63
O3B0.6196 (10)0.5240 (9)0.0694 (16)0.108 (4)0.37
H3C0.63430.47760.03620.162*0.37
H3D0.61490.51870.15910.162*0.37

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.03347 (17)0.02267 (16)0.03967 (19)−0.00084 (11)0.00116 (12)−0.00023 (12)
O10.0486 (6)0.0276 (5)0.0414 (6)−0.0048 (5)0.0064 (5)−0.0029 (5)
O20.0377 (6)0.0376 (6)0.0418 (6)−0.0045 (5)0.0037 (5)−0.0035 (5)
N10.0404 (7)0.0305 (7)0.0378 (8)−0.0036 (5)0.0055 (6)0.0028 (6)
N20.0399 (7)0.0321 (7)0.0380 (8)−0.0036 (6)−0.0035 (6)−0.0019 (6)
N30.0413 (8)0.0309 (7)0.0620 (10)0.0021 (6)−0.0015 (7)−0.0011 (7)
N40.1096 (17)0.0452 (11)0.1228 (19)0.0050 (10)−0.0019 (14)−0.0175 (12)
N50.0858 (15)0.0982 (16)0.1116 (19)0.0178 (12)−0.0413 (15)0.0107 (13)
C10.0485 (10)0.0441 (10)0.0410 (10)−0.0025 (7)0.0006 (8)0.0083 (8)
C20.0592 (11)0.0422 (10)0.0548 (12)0.0059 (8)0.0086 (9)0.0175 (9)
C30.0689 (12)0.0290 (9)0.0611 (13)−0.0025 (8)0.0147 (10)0.0080 (8)
C40.0546 (11)0.0361 (9)0.0522 (11)−0.0107 (8)0.0053 (8)−0.0011 (8)
C50.0375 (8)0.0324 (8)0.0421 (9)−0.0057 (6)0.0030 (7)0.0019 (7)
C60.0389 (9)0.0327 (8)0.0457 (10)−0.0061 (6)−0.0015 (7)0.0003 (7)
C70.0401 (10)0.0592 (12)0.0771 (15)−0.0072 (9)0.0000 (9)0.0098 (11)
C80.0439 (11)0.0753 (15)0.0897 (17)0.0017 (10)−0.0113 (11)0.0099 (13)
C90.0636 (14)0.0550 (12)0.0692 (15)0.0087 (10)−0.0214 (11)0.0057 (10)
C100.0594 (11)0.0387 (10)0.0475 (11)−0.0013 (8)−0.0091 (9)0.0075 (8)
C110.0370 (9)0.0349 (9)0.0481 (10)−0.0006 (7)0.0030 (7)−0.0011 (7)
C120.0464 (10)0.0353 (9)0.0590 (12)0.0099 (7)0.0019 (9)0.0029 (8)
C130.0659 (13)0.0389 (11)0.0748 (15)0.0136 (9)0.0073 (11)−0.0003 (10)
C140.0626 (13)0.0488 (11)0.0688 (14)0.0153 (9)−0.0046 (11)0.0099 (10)
O30.118 (4)0.0587 (17)0.058 (2)0.012 (3)0.015 (3)−0.0030 (15)
O3B0.164 (11)0.086 (4)0.075 (5)0.034 (8)0.018 (8)−0.002 (4)

Geometric parameters (Å, °)

Co1—O22.0503 (11)C4—H40.9300
Co1—O2i2.0503 (11)C5—C61.478 (2)
Co1—O12.0691 (11)C6—C71.378 (2)
Co1—O1i2.0691 (11)C7—C81.367 (3)
Co1—N3i2.1093 (14)C7—H70.9300
Co1—N32.1093 (14)C8—C91.359 (3)
O1—N11.3346 (16)C8—H80.9300
O2—N21.3318 (16)C9—C101.378 (3)
N1—C11.340 (2)C9—H90.9300
N1—C51.353 (2)C10—H100.9300
N2—C101.342 (2)C11—C121.396 (2)
N2—C61.350 (2)C12—C141.400 (3)
N3—C111.145 (2)C12—C131.401 (3)
N4—C131.140 (3)O3—H3A0.8567
N5—C141.134 (3)O3—H3B0.8584
C1—C21.374 (3)O3—H3C1.0384
C1—H10.9300O3—H3D1.0555
C2—C31.362 (3)O3B—H3A1.0017
C2—H20.9300O3B—H3B1.0464
C3—C41.379 (3)O3B—H3C0.8522
C3—H30.9300O3B—H3D0.8564
C4—C51.376 (2)
O2—Co1—O2i180.00 (5)N1—C5—C4118.94 (15)
O2—Co1—O185.58 (5)N1—C5—C6118.18 (13)
O2i—Co1—O194.42 (5)C4—C5—C6122.86 (15)
O2—Co1—O1i94.42 (5)N2—C6—C7118.58 (16)
O2i—Co1—O1i85.58 (5)N2—C6—C5118.84 (14)
O1—Co1—O1i180.00 (5)C7—C6—C5122.49 (15)
O2—Co1—N3i93.91 (5)C8—C7—C6120.92 (19)
O2i—Co1—N3i86.09 (5)C8—C7—H7119.5
O1—Co1—N3i86.63 (5)C6—C7—H7119.5
O1i—Co1—N3i93.37 (5)C9—C8—C7118.97 (19)
O2—Co1—N386.09 (5)C9—C8—H8120.5
O2i—Co1—N393.91 (5)C7—C8—H8120.5
O1—Co1—N393.37 (5)C8—C9—C10120.15 (18)
O1i—Co1—N386.63 (5)C8—C9—H9119.9
N3i—Co1—N3180.0C10—C9—H9119.9
N1—O1—Co1114.83 (9)N2—C10—C9119.79 (17)
N2—O2—Co1116.72 (9)N2—C10—H10120.1
O1—N1—C1119.17 (13)C9—C10—H10120.1
O1—N1—C5119.23 (12)N3—C11—C12179.43 (19)
C1—N1—C5121.60 (14)C11—C12—C14118.80 (16)
O2—N2—C10119.10 (14)C11—C12—C13119.73 (16)
O2—N2—C6119.31 (12)C14—C12—C13121.46 (15)
C10—N2—C6121.56 (15)N4—C13—C12179.0 (2)
C11—N3—Co1166.34 (15)N5—C14—C12176.8 (3)
N1—C1—C2119.85 (16)H3A—O3—H3B106.1
N1—C1—H1120.1H3A—O3—H3C32.7
C2—C1—H1120.1H3B—O3—H3C117.5
C3—C2—C1120.34 (16)H3A—O3—H3D82.0
C3—C2—H2119.8H3B—O3—H3D36.9
C1—C2—H2119.8H3C—O3—H3D82.1
C2—C3—C4118.89 (17)H3A—O3B—H3B84.0
C2—C3—H3120.6H3A—O3B—H3C34.1
C4—C3—H3120.6H3B—O3B—H3C117.3
C5—C4—C3120.36 (17)H3A—O3B—H3D85.3
C5—C4—H4119.8H3B—O3B—H3D37.3
C3—C4—H4119.8H3C—O3B—H3D107.2

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3B···O10.862.002.851 (8)173
O3B—H3D···O10.862.092.890 (15)156
O3—H3A···N4ii0.862.243.028 (8)152
O3B—H3C···N4ii0.852.213.056 (15)174
C1—H1···N4iii0.932.553.437 (3)161
C4—H4···N5iv0.932.383.287 (3)165
C10—H10···N4v0.932.483.390 (3)164

Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x+1, −y+3/2, z+1/2; (v) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2560).

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