Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page m1134
https://doi.org/10.1107/S160053681003254X

Di­chloridobis(3,4,5-tri­methyl-1H-pyrazole-κN2)cobalt(II)

Ganna Lyubartsevaa* and Sean Parkinb

aDepartment of Chemistry and Physics, College of Science and Technology, Southern Arkansas University, Magnolia, AR 71753, USA, and bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
*Correspondence e-mail: GannaLyubartseva@saumag.edu

(Received 11 August 2010; accepted 12 August 2010; online 21 August 2010)

In the title compound, [CoIICl2(C6H10N2)2], a pair of 3,4,5-trimethyl­pyrazoles act as monodentate ligands. Two Cl− anions are also bonded directly to the CoII atom, which has a CoN2Cl2 chromophore in a slightly distorted tetra­hedral geometry. The two mol­ecules in the asymmetric unit are related by an approximate twofold rotation roughly parallel to the a axis. The amino H atom in the pyrazole ring participates in weak N—H⋯Cl hydrogen bonds to form chains that propagate roughly parallel to the c axis.

Related literature

For a similar tetra­hedral complex with pyrazole, see: Zyryanova et al. (2005[Zyryanova, I. A., Baikalova, L. V., Tarasova, O. A., Afonin, A. V., Kukhareva, V. A., Maksimova, M. A. & Trofimov, B. A. (2005). Russ. J. Gen. Chem. 75, 1283-1289.]). For thermal decomposition studies, see: Petrovic et al. (1993[Petrovic, A. F., Skuban, S. J. & Lukic, S. R. (1993). Zbornik Matice Srpske za Prirodne Nauke, 85, 361-365.]). For a similar tetra­hedral complex with 3,5-dimethyl­pyrazole, see: Leovac et al. (2007[Leovac, V. M., Petkovic, R., Kovacs, A., Pokol, G. & Szecsenyi, K. M. (2007). J. Therm. Anal. Calorim. 89, 267-275.]). For potential catalytic applications, see: Li et al. (2009[Li, T., Liang, B. & Tang, Sh. (2009). Huaxue Fanying Gongcheng Yu Gongyi, 25, 142-147.]); Oki et al. (1995[Oki, A. R., Sanchez, J., Hamilton, S. & Emge, T. J. (1995). J. Coord. Chem. 36, 63-69.]). For additional related complexes, see: Sheu et al. (1996[Sheu, S., Tien, M., Cheng, M., Ho, T., Peng, S. & Lin, Y. (1996). Polyhedron, 15, 961-965.]); Lyubartseva & Parkin (2010[Lyubartseva, G. & Parkin, S. (2010). Acta Cryst. E66, m475-m476.]).

[Scheme 1]

Experimental

Crystal data

  • [CoCl2(C6H10N2)2]

  • Mr = 350.15

  • Orthorhombic, P b c a

  • a = 14.8880 (1) Å

  • b = 17.3980 (1) Å

  • c = 24.9220 (2) Å

  • V = 6455.33 (8) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 1.39 mm−1

  • T = 90 K

  • 0.30 × 0.28 × 0.19 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.590, Tmax = 0.746

  • 111609 measured reflections

  • 7404 independent reflections

  • 5822 reflections with I > 2σ(I)

  • Rint = 0.064
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.111

  • S = 1.15

  • 7404 reflections

  • 355 parameters

  • H-atom parameters constrained

  • Δρmax = 0.80 e Å−3

  • Δρmin = −0.60 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—H2A⋯Cl2Bi 0.88 2.55 3.290 (2) 142
N2A—H2A⋯Cl2A 0.88 2.86 3.373 (2) 118
N4A—H4A⋯Cl1Bii 0.88 2.61 3.416 (2) 152
N4A—H4A⋯Cl1A 0.88 2.79 3.309 (2) 119
N2B—H2B⋯Cl2Aiii 0.88 2.70 3.456 (2) 145
N2B—H2B⋯Cl2B 0.88 2.76 3.286 (2) 119
N4B—H4B⋯Cl1Aiv 0.88 2.57 3.363 (2) 150
N4B—H4B⋯Cl1B 0.88 2.86 3.365 (2) 118
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and local procedures.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681003254X/ng5017sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003254X/ng5017Isup2.hkl

checkCIF report


Comment top

Pyrazole complexes with transition metals are very important because of their similarities to regular constituents of proteins. They can also be potentially useful for catalysis (Li et al. 2009) and magnetism studies (Oki et al. 1995). To obtain a tetrahedral complex geometry it is often necessary to engineer the pyrazole ligand with different connectivity (Sheu et al. 1996). Here we report that the introduction of one more methyl group in the pyrazole ring at 4 position, in addition to 3 and 5 position, results in the efficient formation of a tetrahedral geometry.

The synthesis and characterization of the cobalt co-ordination compound containing the 3,4,5-trimethylpyrazole ligand is described. The compound has the formula CoII(C6H10N2)2Cl2 and been characterized by several spectroscopic methods and analytical techniques. 3,4,5-Trimethylpyrazole acts as a monodentate ligand and the anions are also bonded directly with the metal center. The cobalt atom has a CoN2Cl2 chromophore in a distorted tetrahedral geometry. Co–N distances are 2.004 (2) and 2.012 (2)Å for the pyrazole N atoms. Co–Cl distances are 2.2536 (7) and 2.2617 (7) Å. The amine hydrogen in the pyrazole ring participates in weak N—H—Cl hydrogen bonds to form chains that propagate roughly parallel to the c axis direction.

Related literature top

For a similar tetrahedral complex with pyrazole, see: Zyryanova et al. (2005). For thermal decomposition studies, see: Petrovic et al. (1993). For a similar tetrahedral complex with 3,5-dimethylpyrazole, see: Leovac et al. (2007). For potential catalytic applications, see: Li et al. (2009); Oki et al. (1995). For additional related complexes, see: Sheu et al. (1996); Lyubartseva & Parkin (2010).

Experimental top

CoCl2.6H2O (0.714 g, 3 mmol) was added to 3,4,5-trimethylpyrazole (0.668 g, 6 mmol) in a 50 ml round bottom flask and 20 ml tetrahydrofuran added to the reaction mixture with stirring. After 5 minutes stirring, the blue color reaction mixture was filtered and the filtrate was added drop wise to 500 ml of hexane with vigorous stirring. The resulting powder was filtered and found to be [bis(3,4,5-trimethylpyrazole)]-dichlorocobalt(II) (0.698 g, Yield=66.4%). For structure determination, this powder was dissolved in methylene chloride and layerd with hexane. Blue colored, analytically pure orthorhombic crystals were obtained after 3 days. Elemental analysis calculated for CoC12H20N4Cl2: C 41.16, H 5.76, N 16.00; found C 41.11, H 5.69, N 16.08. IR(cm-1) 3310, 2925, 1581, 1530, 1446, 1404, 1377, 1266, 1199, 1159, 1125, 1018, 950, 765, 697, 683, 598, 566, 490.

Refinement top

H atoms were found in difference Fourier maps and subsequently placed in idealized positions with constrained distances of 0.98 Å (RCH3), 0.88 Å (N—H), and with Uiso(H) values set to either 1.2Ueq or 1.5Ueq (RCH3) of the attached atom.

Structure description top

Pyrazole complexes with transition metals are very important because of their similarities to regular constituents of proteins. They can also be potentially useful for catalysis (Li et al. 2009) and magnetism studies (Oki et al. 1995). To obtain a tetrahedral complex geometry it is often necessary to engineer the pyrazole ligand with different connectivity (Sheu et al. 1996). Here we report that the introduction of one more methyl group in the pyrazole ring at 4 position, in addition to 3 and 5 position, results in the efficient formation of a tetrahedral geometry.

The synthesis and characterization of the cobalt co-ordination compound containing the 3,4,5-trimethylpyrazole ligand is described. The compound has the formula CoII(C6H10N2)2Cl2 and been characterized by several spectroscopic methods and analytical techniques. 3,4,5-Trimethylpyrazole acts as a monodentate ligand and the anions are also bonded directly with the metal center. The cobalt atom has a CoN2Cl2 chromophore in a distorted tetrahedral geometry. Co–N distances are 2.004 (2) and 2.012 (2)Å for the pyrazole N atoms. Co–Cl distances are 2.2536 (7) and 2.2617 (7) Å. The amine hydrogen in the pyrazole ring participates in weak N—H—Cl hydrogen bonds to form chains that propagate roughly parallel to the c axis direction.

For a similar tetrahedral complex with pyrazole, see: Zyryanova et al. (2005). For thermal decomposition studies, see: Petrovic et al. (1993). For a similar tetrahedral complex with 3,5-dimethylpyrazole, see: Leovac et al. (2007). For potential catalytic applications, see: Li et al. (2009); Oki et al. (1995). For additional related complexes, see: Sheu et al. (1996); Lyubartseva & Parkin (2010).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); 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: SHELXL97 (Sheldrick, 2008) and local procedures.

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Dichloridobis(3,4,5-trimethyl-1H-pyrazole-κN2)cobalt(II) top
Crystal data top
[CoCl2(C6H10N2)2]F(000) = 2896
Mr = 350.15Dx = 1.441 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 15242 reflections
a = 14.8880 (1) Åθ = 1.0–27.5°
b = 17.3980 (1) ŵ = 1.39 mm−1
c = 24.9220 (2) ÅT = 90 K
V = 6455.33 (8) Å3Block, blue
Z = 160.30 × 0.28 × 0.19 mm
Data collection top
Nonius KappaCCD
diffractometer		7404 independent reflections
Radiation source: fine-focus sealed tube5822 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
Detector resolution: 9.1 pixels mm-1θmax = 27.5°, θmin = 1.6°
ω scans at fixed χ = 55°h = −19→19
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)		k = −22→22
Tmin = 0.590, Tmax = 0.746l = −32→32
111609 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0507P)2 + 7.0674P]
where P = (Fo2 + 2Fc2)/3
7404 reflections(Δ/σ)max = 0.001
355 parametersΔρmax = 0.80 e Å−3
0 restraintsΔρmin = −0.60 e Å−3
Crystal data top
[CoCl2(C6H10N2)2]V = 6455.33 (8) Å3
Mr = 350.15Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 14.8880 (1) ŵ = 1.39 mm−1
b = 17.3980 (1) ÅT = 90 K
c = 24.9220 (2) Å0.30 × 0.28 × 0.19 mm
Data collection top
Nonius KappaCCD
diffractometer		7404 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)		5822 reflections with I > 2σ(I)
Tmin = 0.590, Tmax = 0.746Rint = 0.064
111609 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.15Δρmax = 0.80 e Å−3
7404 reflectionsΔρmin = −0.60 e Å−3
355 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
Co1A0.70074 (2)0.11088 (2)0.365286 (14)0.01780 (10)
Cl1A0.73843 (5)0.00580 (4)0.31744 (3)0.02255 (15)
Cl2A0.80296 (5)0.16183 (4)0.42223 (3)0.02503 (15)
N1A0.59573 (15)0.09270 (13)0.41394 (9)0.0205 (5)
N2A0.59238 (15)0.12310 (13)0.46421 (8)0.0211 (5)
H2A0.63750.14680.47990.025*
N3A0.66803 (15)0.18364 (13)0.30568 (8)0.0196 (5)
N4A0.66770 (14)0.16085 (12)0.25323 (8)0.0179 (4)
H4A0.68120.11420.24230.021*
C1A0.51360 (18)0.06308 (14)0.40500 (10)0.0192 (5)
C2A0.45852 (19)0.07446 (15)0.44974 (10)0.0218 (6)
C3A0.51108 (19)0.11215 (15)0.48690 (11)0.0223 (6)
C4A0.49183 (19)0.02581 (17)0.35250 (11)0.0268 (6)
H4A10.49780.06360.32360.040*
H4A20.43010.00630.35340.040*
H4A30.5334−0.01690.34620.040*
C5A0.36239 (19)0.05170 (19)0.45728 (12)0.0306 (7)
H5A10.35340.03350.49410.046*
H5A20.34720.01050.43200.046*
H5A30.32360.09620.45060.046*
C6A0.4881 (2)0.13878 (18)0.54196 (11)0.0290 (6)
H6A10.54320.15250.56120.044*
H6A20.45700.09750.56130.044*
H6A30.44880.18390.53970.044*
C7A0.64302 (17)0.25790 (15)0.30523 (11)0.0195 (5)
C8A0.62787 (17)0.28238 (15)0.25262 (11)0.0203 (5)
C9A0.64395 (17)0.21919 (15)0.22035 (10)0.0189 (5)
C10A0.6328 (2)0.30248 (16)0.35591 (11)0.0258 (6)
H10A0.56890.31140.36290.039*
H10B0.66380.35190.35240.039*
H10C0.65910.27340.38570.039*
C11A0.60097 (19)0.36179 (15)0.23513 (12)0.0257 (6)
H11A0.60740.36620.19610.039*
H11B0.63970.39980.25270.039*
H11C0.53830.37120.24510.039*
C12A0.6347 (2)0.20858 (17)0.16140 (10)0.0261 (6)
H12A0.66670.16190.15040.039*
H12B0.66030.25310.14280.039*
H12C0.57100.20370.15210.039*
Co1B0.31918 (2)0.40924 (2)0.373980 (14)0.01860 (10)
Cl1B0.27079 (5)0.51575 (4)0.33151 (3)0.02458 (16)
Cl2B0.22703 (5)0.34966 (4)0.43286 (3)0.02729 (16)
N1B0.42685 (15)0.42502 (13)0.42153 (9)0.0206 (5)
N2B0.43489 (16)0.38675 (13)0.46881 (8)0.0217 (5)
H2B0.39080.36160.48440.026*
N3B0.34707 (15)0.33970 (13)0.31166 (8)0.0194 (5)
N4B0.34550 (15)0.36468 (12)0.25999 (8)0.0192 (5)
H4B0.33200.41190.25030.023*
C1B0.50868 (18)0.45440 (15)0.41148 (10)0.0203 (5)
C2B0.56832 (18)0.43508 (15)0.45274 (11)0.0211 (5)
C3B0.51843 (18)0.39196 (15)0.48875 (10)0.0211 (6)
C4B0.52534 (19)0.49953 (17)0.36144 (11)0.0259 (6)
H4B10.55350.46630.33450.039*
H4B20.56530.54280.36950.039*
H4B30.46820.51900.34750.039*
C5B0.66573 (19)0.45395 (18)0.45800 (12)0.0286 (6)
H5B10.67630.47990.49230.043*
H5B20.68380.48790.42850.043*
H5B30.70110.40650.45660.043*
C6B0.5461 (2)0.35618 (17)0.54041 (11)0.0283 (6)
H6B10.49260.34040.56050.042*
H6B20.58030.39350.56160.042*
H6B30.58370.31110.53320.042*
C7B0.37141 (17)0.26534 (15)0.30912 (11)0.0198 (5)
C8B0.38400 (18)0.24321 (15)0.25563 (11)0.0204 (5)
C9B0.36707 (17)0.30816 (15)0.22547 (10)0.0191 (5)
C10B0.3832 (2)0.21733 (17)0.35834 (11)0.0284 (6)
H10D0.44720.20730.36410.043*
H10E0.35130.16850.35380.043*
H10F0.35870.24470.38940.043*
C11B0.41032 (19)0.16500 (15)0.23556 (11)0.0251 (6)
H11D0.40180.16270.19660.038*
H11E0.37280.12590.25280.038*
H11F0.47360.15540.24410.038*
C12B0.37356 (19)0.32148 (16)0.16644 (10)0.0239 (6)
H12D0.34120.36860.15710.036*
H12E0.34700.27780.14730.036*
H12F0.43680.32670.15620.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co1A0.01982 (19)0.01854 (19)0.01504 (18)0.00059 (14)−0.00063 (13)0.00002 (13)
Cl1A0.0250 (3)0.0212 (3)0.0215 (3)0.0030 (3)−0.0011 (3)−0.0038 (2)
Cl2A0.0271 (4)0.0282 (3)0.0198 (3)−0.0053 (3)−0.0059 (3)0.0020 (3)
N1A0.0224 (12)0.0221 (11)0.0170 (11)0.0012 (9)−0.0023 (9)−0.0016 (9)
N2A0.0228 (12)0.0264 (12)0.0140 (11)−0.0016 (9)−0.0001 (9)−0.0019 (9)
N3A0.0226 (12)0.0205 (11)0.0158 (11)0.0007 (9)−0.0003 (9)−0.0010 (9)
N4A0.0189 (11)0.0192 (11)0.0156 (10)0.0009 (9)−0.0016 (8)−0.0012 (8)
C1A0.0212 (13)0.0163 (12)0.0202 (13)0.0009 (10)−0.0024 (10)0.0017 (10)
C2A0.0230 (14)0.0222 (13)0.0202 (13)0.0014 (11)−0.0001 (11)0.0025 (11)
C3A0.0248 (14)0.0225 (13)0.0197 (13)0.0022 (11)0.0027 (11)0.0019 (10)
C4A0.0224 (14)0.0328 (16)0.0254 (15)0.0015 (12)−0.0029 (12)−0.0062 (12)
C5A0.0255 (15)0.0382 (17)0.0280 (15)−0.0046 (13)0.0010 (12)0.0020 (13)
C6A0.0288 (16)0.0378 (17)0.0204 (14)0.0002 (13)0.0046 (12)−0.0023 (12)
C7A0.0177 (13)0.0187 (13)0.0222 (13)−0.0005 (10)0.0000 (10)−0.0015 (10)
C8A0.0166 (13)0.0201 (13)0.0241 (14)−0.0002 (10)−0.0010 (10)0.0004 (11)
C9A0.0163 (12)0.0214 (13)0.0191 (13)−0.0008 (10)−0.0023 (10)0.0025 (10)
C10A0.0291 (15)0.0228 (14)0.0255 (14)0.0043 (12)−0.0019 (12)−0.0049 (11)
C11A0.0256 (15)0.0220 (14)0.0295 (15)0.0019 (11)−0.0064 (12)0.0038 (11)
C12A0.0312 (16)0.0290 (15)0.0180 (13)−0.0003 (12)−0.0025 (11)0.0044 (11)
Co1B0.02032 (19)0.01980 (19)0.01568 (18)0.00110 (14)0.00118 (14)−0.00009 (14)
Cl1B0.0278 (4)0.0231 (3)0.0228 (3)0.0049 (3)0.0012 (3)0.0036 (3)
Cl2B0.0298 (4)0.0324 (4)0.0197 (3)−0.0072 (3)0.0068 (3)−0.0024 (3)
N1B0.0229 (12)0.0228 (11)0.0161 (11)−0.0006 (9)0.0005 (9)0.0013 (9)
N2B0.0250 (12)0.0245 (12)0.0155 (11)0.0001 (9)0.0014 (9)0.0033 (9)
N3B0.0211 (11)0.0222 (11)0.0150 (10)0.0013 (9)0.0015 (9)0.0021 (9)
N4B0.0225 (12)0.0192 (11)0.0158 (11)0.0011 (9)0.0014 (9)0.0027 (8)
C1B0.0222 (14)0.0202 (13)0.0186 (13)0.0015 (11)0.0012 (10)−0.0012 (10)
C2B0.0213 (14)0.0213 (13)0.0208 (13)0.0031 (11)−0.0003 (11)−0.0021 (11)
C3B0.0236 (14)0.0219 (13)0.0179 (13)0.0036 (11)−0.0004 (11)−0.0035 (10)
C4B0.0221 (14)0.0305 (15)0.0249 (15)−0.0003 (12)0.0014 (11)0.0042 (12)
C5B0.0257 (15)0.0319 (16)0.0282 (15)−0.0009 (12)−0.0024 (12)0.0016 (12)
C6B0.0307 (16)0.0327 (16)0.0216 (14)0.0004 (13)−0.0014 (12)0.0023 (12)
C7B0.0183 (13)0.0182 (13)0.0229 (14)−0.0003 (10)0.0005 (10)−0.0006 (10)
C8B0.0172 (13)0.0216 (13)0.0224 (13)−0.0007 (10)0.0013 (10)−0.0017 (11)
C9B0.0159 (13)0.0216 (13)0.0197 (13)−0.0029 (10)0.0017 (10)−0.0039 (10)
C10B0.0346 (17)0.0256 (15)0.0250 (15)0.0044 (13)0.0016 (12)0.0044 (12)
C11B0.0246 (15)0.0208 (14)0.0299 (15)0.0027 (11)0.0032 (12)−0.0050 (11)
C12B0.0289 (15)0.0241 (14)0.0188 (13)−0.0027 (11)0.0013 (11)−0.0006 (11)
Geometric parameters (Å, º) top
Co1A—N1A2.004 (2)Co1B—N3B2.012 (2)
Co1A—N3A2.012 (2)Co1B—N1B2.012 (2)
Co1A—Cl1A2.2536 (7)Co1B—Cl1B2.2524 (7)
Co1A—Cl2A2.2617 (7)Co1B—Cl2B2.2606 (7)
N1A—C1A1.346 (3)N1B—C1B1.345 (3)
N1A—N2A1.361 (3)N1B—N2B1.359 (3)
N2A—C3A1.350 (3)N2B—C3B1.342 (4)
N2A—H2A0.8800N2B—H2B0.8800
N3A—C7A1.345 (3)N3B—C7B1.345 (3)
N3A—N4A1.366 (3)N3B—N4B1.359 (3)
N4A—C9A1.352 (3)N4B—C9B1.345 (3)
N4A—H4A0.8800N4B—H4B0.8800
C1A—C2A1.398 (4)C1B—C2B1.400 (4)
C1A—C4A1.496 (4)C1B—C4B1.494 (4)
C2A—C3A1.378 (4)C2B—C3B1.386 (4)
C2A—C5A1.497 (4)C2B—C5B1.493 (4)
C3A—C6A1.488 (4)C3B—C6B1.488 (4)
C4A—H4A10.9800C4B—H4B10.9800
C4A—H4A20.9800C4B—H4B20.9800
C4A—H4A30.9800C4B—H4B30.9800
C5A—H5A10.9800C5B—H5B10.9800
C5A—H5A20.9800C5B—H5B20.9800
C5A—H5A30.9800C5B—H5B30.9800
C6A—H6A10.9800C6B—H6B10.9800
C6A—H6A20.9800C6B—H6B20.9800
C6A—H6A30.9800C6B—H6B30.9800
C7A—C8A1.397 (4)C7B—C8B1.400 (4)
C7A—C10A1.490 (4)C7B—C10B1.494 (4)
C8A—C9A1.383 (4)C8B—C9B1.380 (4)
C8A—C11A1.503 (4)C8B—C11B1.502 (4)
C9A—C12A1.487 (4)C9B—C12B1.493 (4)
C10A—H10A0.9800C10B—H10D0.9800
C10A—H10B0.9800C10B—H10E0.9800
C10A—H10C0.9800C10B—H10F0.9800
C11A—H11A0.9800C11B—H11D0.9800
C11A—H11B0.9800C11B—H11E0.9800
C11A—H11C0.9800C11B—H11F0.9800
C12A—H12A0.9800C12B—H12D0.9800
C12A—H12B0.9800C12B—H12E0.9800
C12A—H12C0.9800C12B—H12F0.9800
N1A—Co1A—N3A110.94 (9)N3B—Co1B—N1B111.86 (9)
N1A—Co1A—Cl1A112.73 (7)N3B—Co1B—Cl1B101.42 (6)
N3A—Co1A—Cl1A100.38 (6)N1B—Co1B—Cl1B114.79 (7)
N1A—Co1A—Cl2A101.96 (7)N3B—Co1B—Cl2B110.52 (7)
N3A—Co1A—Cl2A112.31 (7)N1B—Co1B—Cl2B99.43 (7)
Cl1A—Co1A—Cl2A118.84 (3)Cl1B—Co1B—Cl2B119.22 (3)
C1A—N1A—N2A105.5 (2)C1B—N1B—N2B105.6 (2)
C1A—N1A—Co1A132.03 (18)C1B—N1B—Co1B131.60 (18)
N2A—N1A—Co1A121.63 (17)N2B—N1B—Co1B120.93 (17)
C3A—N2A—N1A111.3 (2)C3B—N2B—N1B111.7 (2)
C3A—N2A—H2A124.3C3B—N2B—H2B124.2
N1A—N2A—H2A124.3N1B—N2B—H2B124.2
C7A—N3A—N4A105.7 (2)C7B—N3B—N4B105.5 (2)
C7A—N3A—Co1A132.68 (18)C7B—N3B—Co1B132.09 (18)
N4A—N3A—Co1A121.65 (16)N4B—N3B—Co1B122.38 (16)
C9A—N4A—N3A111.3 (2)C9B—N4B—N3B111.6 (2)
C9A—N4A—H4A124.4C9B—N4B—H4B124.2
N3A—N4A—H4A124.4N3B—N4B—H4B124.2
N1A—C1A—C2A110.3 (2)N1B—C1B—C2B110.3 (2)
N1A—C1A—C4A120.5 (2)N1B—C1B—C4B120.4 (2)
C2A—C1A—C4A129.2 (2)C2B—C1B—C4B129.3 (2)
C3A—C2A—C1A105.7 (2)C3B—C2B—C1B105.4 (2)
C3A—C2A—C5A125.7 (3)C3B—C2B—C5B125.7 (3)
C1A—C2A—C5A128.6 (3)C1B—C2B—C5B128.9 (3)
N2A—C3A—C2A107.1 (2)N2B—C3B—C2B107.1 (2)
N2A—C3A—C6A123.3 (3)N2B—C3B—C6B123.3 (3)
C2A—C3A—C6A129.6 (3)C2B—C3B—C6B129.7 (3)
C1A—C4A—H4A1109.5C1B—C4B—H4B1109.5
C1A—C4A—H4A2109.5C1B—C4B—H4B2109.5
H4A1—C4A—H4A2109.5H4B1—C4B—H4B2109.5
C1A—C4A—H4A3109.5C1B—C4B—H4B3109.5
H4A1—C4A—H4A3109.5H4B1—C4B—H4B3109.5
H4A2—C4A—H4A3109.5H4B2—C4B—H4B3109.5
C2A—C5A—H5A1109.5C2B—C5B—H5B1109.5
C2A—C5A—H5A2109.5C2B—C5B—H5B2109.5
H5A1—C5A—H5A2109.5H5B1—C5B—H5B2109.5
C2A—C5A—H5A3109.5C2B—C5B—H5B3109.5
H5A1—C5A—H5A3109.5H5B1—C5B—H5B3109.5
H5A2—C5A—H5A3109.5H5B2—C5B—H5B3109.5
C3A—C6A—H6A1109.5C3B—C6B—H6B1109.5
C3A—C6A—H6A2109.5C3B—C6B—H6B2109.5
H6A1—C6A—H6A2109.5H6B1—C6B—H6B2109.5
C3A—C6A—H6A3109.5C3B—C6B—H6B3109.5
H6A1—C6A—H6A3109.5H6B1—C6B—H6B3109.5
H6A2—C6A—H6A3109.5H6B2—C6B—H6B3109.5
N3A—C7A—C8A110.2 (2)N3B—C7B—C8B110.2 (2)
N3A—C7A—C10A121.4 (2)N3B—C7B—C10B122.0 (2)
C8A—C7A—C10A128.4 (2)C8B—C7B—C10B127.7 (2)
C9A—C8A—C7A106.0 (2)C9B—C8B—C7B105.6 (2)
C9A—C8A—C11A127.5 (2)C9B—C8B—C11B127.5 (2)
C7A—C8A—C11A126.6 (2)C7B—C8B—C11B127.0 (2)
N4A—C9A—C8A106.8 (2)N4B—C9B—C8B107.1 (2)
N4A—C9A—C12A122.0 (2)N4B—C9B—C12B122.2 (2)
C8A—C9A—C12A131.1 (2)C8B—C9B—C12B130.7 (2)
C7A—C10A—H10A109.5C7B—C10B—H10D109.5
C7A—C10A—H10B109.5C7B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
C7A—C10A—H10C109.5C7B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
C8A—C11A—H11A109.5C8B—C11B—H11D109.5
C8A—C11A—H11B109.5C8B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C8A—C11A—H11C109.5C8B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
C9A—C12A—H12A109.5C9B—C12B—H12D109.5
C9A—C12A—H12B109.5C9B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C9A—C12A—H12C109.5C9B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
N3A—Co1A—N1A—C1A60.6 (3)N3B—Co1B—N1B—C1B59.8 (3)
Cl1A—Co1A—N1A—C1A−51.1 (2)Cl1B—Co1B—N1B—C1B−55.1 (3)
Cl2A—Co1A—N1A—C1A−179.6 (2)Cl2B—Co1B—N1B—C1B176.5 (2)
N3A—Co1A—N1A—N2A−107.49 (19)N3B—Co1B—N1B—N2B−101.98 (19)
Cl1A—Co1A—N1A—N2A140.83 (17)Cl1B—Co1B—N1B—N2B143.17 (17)
Cl2A—Co1A—N1A—N2A12.3 (2)Cl2B—Co1B—N1B—N2B14.73 (19)
C1A—N1A—N2A—C3A0.9 (3)C1B—N1B—N2B—C3B0.6 (3)
Co1A—N1A—N2A—C3A171.76 (17)Co1B—N1B—N2B—C3B166.59 (17)
N1A—Co1A—N3A—C7A63.9 (3)N1B—Co1B—N3B—C7B63.7 (3)
Cl1A—Co1A—N3A—C7A−176.7 (2)Cl1B—Co1B—N3B—C7B−173.5 (2)
Cl2A—Co1A—N3A—C7A−49.4 (3)Cl2B—Co1B—N3B—C7B−46.1 (3)
N1A—Co1A—N3A—N4A−115.55 (19)N1B—Co1B—N3B—N4B−114.79 (19)
Cl1A—Co1A—N3A—N4A3.8 (2)Cl1B—Co1B—N3B—N4B8.0 (2)
Cl2A—Co1A—N3A—N4A131.07 (17)Cl2B—Co1B—N3B—N4B135.43 (18)
C7A—N3A—N4A—C9A0.6 (3)C7B—N3B—N4B—C9B0.7 (3)
Co1A—N3A—N4A—C9A−179.83 (17)Co1B—N3B—N4B—C9B179.50 (17)
N2A—N1A—C1A—C2A−0.3 (3)N2B—N1B—C1B—C2B−0.4 (3)
Co1A—N1A—C1A—C2A−169.78 (19)Co1B—N1B—C1B—C2B−164.27 (19)
N2A—N1A—C1A—C4A178.7 (2)N2B—N1B—C1B—C4B178.9 (2)
Co1A—N1A—C1A—C4A9.2 (4)Co1B—N1B—C1B—C4B15.0 (4)
N1A—C1A—C2A—C3A−0.4 (3)N1B—C1B—C2B—C3B0.1 (3)
C4A—C1A—C2A—C3A−179.3 (3)C4B—C1B—C2B—C3B−179.1 (3)
N1A—C1A—C2A—C5A179.4 (3)N1B—C1B—C2B—C5B178.8 (3)
C4A—C1A—C2A—C5A0.5 (5)C4B—C1B—C2B—C5B−0.4 (5)
N1A—N2A—C3A—C2A−1.2 (3)N1B—N2B—C3B—C2B−0.6 (3)
N1A—N2A—C3A—C6A179.5 (2)N1B—N2B—C3B—C6B179.3 (2)
C1A—C2A—C3A—N2A0.9 (3)C1B—C2B—C3B—N2B0.3 (3)
C5A—C2A—C3A—N2A−178.9 (3)C5B—C2B—C3B—N2B−178.5 (3)
C1A—C2A—C3A—C6A−179.8 (3)C1B—C2B—C3B—C6B−179.6 (3)
C5A—C2A—C3A—C6A0.4 (5)C5B—C2B—C3B—C6B1.6 (5)
N4A—N3A—C7A—C8A−0.7 (3)N4B—N3B—C7B—C8B−0.8 (3)
Co1A—N3A—C7A—C8A179.77 (19)Co1B—N3B—C7B—C8B−179.47 (19)
N4A—N3A—C7A—C10A178.1 (2)N4B—N3B—C7B—C10B178.4 (2)
Co1A—N3A—C7A—C10A−1.4 (4)Co1B—N3B—C7B—C10B−0.2 (4)
N3A—C7A—C8A—C9A0.6 (3)N3B—C7B—C8B—C9B0.7 (3)
C10A—C7A—C8A—C9A−178.1 (3)C10B—C7B—C8B—C9B−178.5 (3)
N3A—C7A—C8A—C11A−178.6 (2)N3B—C7B—C8B—C11B−179.3 (2)
C10A—C7A—C8A—C11A2.7 (5)C10B—C7B—C8B—C11B1.6 (5)
N3A—N4A—C9A—C8A−0.2 (3)N3B—N4B—C9B—C8B−0.3 (3)
N3A—N4A—C9A—C12A−177.4 (2)N3B—N4B—C9B—C12B−177.7 (2)
C7A—C8A—C9A—N4A−0.2 (3)C7B—C8B—C9B—N4B−0.2 (3)
C11A—C8A—C9A—N4A178.9 (3)C11B—C8B—C9B—N4B179.7 (3)
C7A—C8A—C9A—C12A176.6 (3)C7B—C8B—C9B—C12B176.9 (3)
C11A—C8A—C9A—C12A−4.2 (5)C11B—C8B—C9B—C12B−3.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···Cl2Bi0.882.553.290 (2)142
N2A—H2A···Cl2A0.882.863.373 (2)118
N4A—H4A···Cl1Bii0.882.613.416 (2)152
N4A—H4A···Cl1A0.882.793.309 (2)119
N2B—H2B···Cl2Aiii0.882.703.456 (2)145
N2B—H2B···Cl2B0.882.763.286 (2)119
N4B—H4B···Cl1Aiv0.882.573.363 (2)150
N4B—H4B···Cl1B0.882.863.365 (2)118
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z+1; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[CoCl2(C6H10N2)2]
Mr350.15
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)90
a, b, c (Å)14.8880 (1), 17.3980 (1), 24.9220 (2)
V (Å3)6455.33 (8)
Z16
Radiation typeMo Kα
µ (mm−1)1.39
Crystal size (mm)0.30 × 0.28 × 0.19
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.590, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		111609, 7404, 5822
Rint0.064
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.111, 1.15
No. of reflections7404
No. of parameters355
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.80, −0.60

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and local procedures.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···Cl2Bi0.882.553.290 (2)142.1
N2A—H2A···Cl2A0.882.863.373 (2)118.4
N4A—H4A···Cl1Bii0.882.613.416 (2)152.4
N4A—H4A···Cl1A0.882.793.309 (2)119.0
N2B—H2B···Cl2Aiii0.882.703.456 (2)144.9
N2B—H2B···Cl2B0.882.763.286 (2)119.3
N4B—H4B···Cl1Aiv0.882.573.363 (2)150.0
N4B—H4B···Cl1B0.882.863.365 (2)117.9
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z+1; (iv) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

GL gratefully acknowledges the Department of Chemistry and Physics, College of Science and Technology, Southern Arkansas University, for the financial support.

References

First citationLeovac, V. M., Petkovic, R., Kovacs, A., Pokol, G. & Szecsenyi, K. M. (2007). J. Therm. Anal. Calorim. 89, 267–275.  Web of Science CSD CrossRef CAS Google Scholar
 First citationLi, T., Liang, B. & Tang, Sh. (2009). Huaxue Fanying Gongcheng Yu Gongyi, 25, 142–147.  CAS Google Scholar
 First citationLyubartseva, G. & Parkin, S. (2010). Acta Cryst. E66, m475–m476.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOki, A. R., Sanchez, J., Hamilton, S. & Emge, T. J. (1995). J. Coord. Chem. 36, 63–69.  CrossRef CAS Web of Science Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationPetrovic, A. F., Skuban, S. J. & Lukic, S. R. (1993). Zbornik Matice Srpske za Prirodne Nauke, 85, 361–365.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheu, S., Tien, M., Cheng, M., Ho, T., Peng, S. & Lin, Y. (1996). Polyhedron, 15, 961–965.  CAS Google Scholar
 First citationZyryanova, I. A., Baikalova, L. V., Tarasova, O. A., Afonin, A. V., Kukhareva, V. A., Maksimova, M. A. & Trofimov, B. A. (2005). Russ. J. Gen. Chem. 75, 1283–1289.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page m1134
https://doi.org/10.1107/S160053681003254X
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS