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

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ISSN: 2056-9890

Di­chlorido­tetra­kis­(diniconazole)cobalt(II)

aCollege of Sciences, Jiangxi Agricultural University, Nanchang 330045, People's Republic of China
*Correspondence e-mail: niexuliang1981@163.com

(Received 26 July 2011; accepted 3 August 2011; online 11 August 2011)

In the crystal structure of the title compound, [CoCl2(C15H17Cl2N3O)4], the CoII cation lies on an inversion center and has a slightly distorted octa­hedral coordination geometry. The equatorial positions are occupied by four N atoms from four diniconazole [systematic name: (E)-(RS)-1-(2,4-dichloro­phen­yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol] ligands. The axial sites are occupied by two Cl anions. In the two independent organic ligands, the triazole ring is oriented at dihedral angles of 18.28 (14) and 32.15 (14)° with respect to the dichloro­phenyl ring. Inter­molecular O—H⋯Cl hydrogen bonds consolidate the crystal packing.

Related literature

For background to the use of diniconazole as a fungicide, see: Sumitomo Chemical (1984[Sumitomo Chemical. (1984). Jpn Pestic. Soc. 6, 229-236.]); Huang et al. (2003[Huang, X.-G., Zhao, A.-J., Liu, X.-G., Zhou, D.-H. & Zeng, B. (2003). Acta Agric. Univ. Jiangxiensis, 25, 277-288.]). For further synthetic details, see: Fu (2002[Fu, D.-Y. (2002). Chin. J. Pestic. 2, 10-12.]); Xia et al. (2001[Xia, H.-Y., Duan, Z.-X., Tu, Y.-M. & Liu, J.-H. (2001). Chin. J. Pestic. 40, 12, 12-14.]). For similar structures, see: Gao et al. (2001[Gao, J.-S., Ma, D.-S., Ma, Z.-G. & Chen, G.-R. (2001). Chin. J. Mol. Sci. 17, 1, 17-22.]). For our previous work based on diniconazole, see: Xiong et al. (2010[Xiong, Z.-Q., Chen, J.-Z., Wen, S.-H. & Nie, X.-L. (2010). Acta Cryst. E66, o3278.]).

[Scheme 1]

Experimental

Crystal data
  • [CoCl2(C15H17Cl2N3O)4]

  • Mr = 1434.69

  • Triclinic, [P \overline 1]

  • a = 8.800 (2) Å

  • b = 13.729 (4) Å

  • c = 15.145 (4) Å

  • α = 90.918 (3)°

  • β = 98.560 (3)°

  • γ = 106.775 (3)°

  • V = 1729.0 (8) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.69 mm−1

  • T = 296 K

  • 0.25 × 0.21 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS, University of Göttingen, Germany.]) Tmin = 0.847, Tmax = 0.916

  • 12895 measured reflections

  • 6356 independent reflections

  • 4764 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.098

  • S = 1.02

  • 6356 reflections

  • 402 parameters

  • 70 restraints

  • H-atom parameters constrained

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.53 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯Cl5i 0.82 2.35 3.136 (2) 161
O2—H2A⋯Cl5i 0.82 2.32 3.128 (2) 169
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). 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

Diniconazole [(E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2- (1H-1,2,4-triazol-1-yl)-pent-1-en-3-ol] is a highly active triazole fungicide(Sumitomo Chemical, 1984). It is widely used for control of a broad range of fungal diseases in many crops, such as corn, wheat, peanut, grape and apple (Huang et al., 2003. Because of its strong antimicrobial activities and its wide applications, the synthesis of diniconazole(Fu et al., 2002; Xia et al., 2001) and its salts(Gao et al., 2001) have attracted much attention. Recently, our group have reported the crystal structure of diniconazole(Xiong et al., 2010). In this paper, we report the synthesis and crystal structure of a new cobalt(II) complex, (I), incorporating diniconazole.

The asymmetric unit of the title compound, [Co(C15H17Cl2N3O) 4Cl2], consists of one cobalt(II) ion, two diniconazole ligands and one coordinated Cl atom. The Co atom lies on an inversion center and has a slightly distorted octahedral geometry. The equatorial positions are occupied by four N atoms from four (E)-(RS)-1- (2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pent -1-en-3-ol ligands. The axial sites are occupied by two Cl atoms (Fig. 1). The Co—N distance are 2.123 (3) and 2.147 (3) Å and Co—Cl is 2.5222 (9) Å. In the crystal packing, intermolecular O—H···Cl hydrogen bonds(Table 1) link the molecules into chains along the a axis (Fig. 2). The structure of the title compound is isostructural to previously reported zinc (II) complexe constructed by Zn (II) and diniconazole (Gao et al., 2001).

Related literature top

For background to the use of diniconazole as a fungicide, see: Sumitomo Chemical (1984); Huang et al. (2003). For further synthetic details, see: Fu (2002); Xia et al. (2001). For similar structures, see: Gao et al. (2001). For our previous work based on diniconazole, see: Xiong et al. (2010).

Experimental top

CoCl2.6H2O (0.036 g, 0.1 mmol) was dissolved in ethanol (10 ml), and diniconazole (0.063 g, 0.2 mmol) was dissolved in ethanol (10 ml). The CoCl2 solution was added to the diniconazole solution slowly under stirring. The mixture were filtered after stirring for 1 h. Crystals suitable for X-ray analysis were obtained by slow concentration of an ethanol solution.

Refinement top

All H atoms were included in calculated positions and refined as riding atoms, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, with Uiso(H) = 1.5Ueq(C) for methyl H and hydroxy atoms and 1.2Ueq(C) for the others.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 (I), showing the atom-labelling scheme and displacement ellipsoids at the 40% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), showing a hydrogen-bonded three- dimensional framework; H-bonds are shown as dashed lines.
Dichloridotetrakis[(E)-(RS)-1-(2,4-dichlorophenyl)-4,4- dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol]cobalt(II) top
Crystal data top
[CoCl2(C15H17Cl2N3O)4]Z = 1
Mr = 1434.69F(000) = 741
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.800 (2) ÅCell parameters from 5326 reflections
b = 13.729 (4) Åθ = 2.5–27.7°
c = 15.145 (4) ŵ = 0.69 mm1
α = 90.918 (3)°T = 296 K
β = 98.560 (3)°Block, red
γ = 106.775 (3)°0.25 × 0.21 × 0.13 mm
V = 1729.0 (8) Å3
Data collection top
Bruker APEXII CCD
diffractometer
6356 independent reflections
Radiation source: fine-focus sealed tube4764 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
h = 1010
Tmin = 0.847, Tmax = 0.916k = 1616
12895 measured reflectionsl = 1816
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0391P)2 + 0.9781P]
where P = (Fo2 + 2Fc2)/3
6356 reflections(Δ/σ)max < 0.001
402 parametersΔρmax = 0.58 e Å3
70 restraintsΔρmin = 0.53 e Å3
Crystal data top
[CoCl2(C15H17Cl2N3O)4]γ = 106.775 (3)°
Mr = 1434.69V = 1729.0 (8) Å3
Triclinic, P1Z = 1
a = 8.800 (2) ÅMo Kα radiation
b = 13.729 (4) ŵ = 0.69 mm1
c = 15.145 (4) ÅT = 296 K
α = 90.918 (3)°0.25 × 0.21 × 0.13 mm
β = 98.560 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
6356 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
4764 reflections with I > 2σ(I)
Tmin = 0.847, Tmax = 0.916Rint = 0.027
12895 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04070 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.02Δρmax = 0.58 e Å3
6356 reflectionsΔρmin = 0.53 e Å3
402 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
C11.0494 (4)0.3225 (2)0.0361 (2)0.0497 (8)
C20.8863 (4)0.3484 (2)0.0079 (2)0.0489 (7)
H20.83960.38730.04530.059*
C30.7935 (3)0.3154 (2)0.06012 (18)0.0409 (7)
C40.8601 (3)0.2571 (2)0.13991 (17)0.0354 (6)
C51.0255 (3)0.2327 (2)0.16483 (19)0.0431 (7)
H51.07340.19330.21770.052*
C61.1210 (4)0.2648 (2)0.1137 (2)0.0481 (7)
H61.23170.24770.13160.058*
C70.7567 (3)0.2295 (2)0.19802 (17)0.0367 (6)
H70.67850.28310.21660.044*
C80.7633 (3)0.1368 (2)0.22641 (16)0.0311 (6)
C90.8686 (3)0.0379 (2)0.19926 (17)0.0362 (6)
H90.95360.05390.17210.043*
C100.7825 (4)0.0182 (2)0.13025 (19)0.0497 (8)
C110.6677 (4)0.0643 (3)0.1702 (3)0.0714 (10)
H11A0.72290.10410.22440.107*
H11B0.57770.01070.18310.107*
H11C0.63030.10720.12820.107*
C120.9126 (5)0.1039 (3)0.0983 (3)0.0819 (12)
H12A0.96610.15300.14720.123*
H12B0.86410.13650.05110.123*
H12C0.98930.07620.07640.123*
C130.6918 (5)0.0564 (3)0.0503 (2)0.0814 (12)
H13A0.65320.01970.00290.122*
H13B0.60240.10630.06830.122*
H13C0.76290.08990.02960.122*
N30.4927 (3)0.18374 (18)0.26583 (15)0.0424 (4)
C150.6774 (3)0.0721 (2)0.36012 (17)0.0359 (4)
H150.77710.02940.38650.043*
C160.6166 (3)0.2063 (2)0.4043 (2)0.0490 (8)
H160.51210.21040.39070.059*
C170.8114 (3)0.15788 (19)0.45944 (17)0.0330 (6)
H170.87640.12350.49150.040*
C181.0204 (3)0.27636 (18)0.38500 (17)0.0305 (6)
C191.1615 (3)0.27996 (19)0.45688 (17)0.0339 (6)
H191.25700.29440.42760.041*
C201.1966 (3)0.3632 (2)0.53304 (19)0.0434 (7)
C211.0705 (4)0.3406 (3)0.5948 (2)0.0609 (9)
H21A1.05690.27340.61540.091*
H21B0.97010.34480.56280.091*
H21C1.10500.38960.64520.091*
C221.3596 (4)0.3668 (3)0.5869 (2)0.0714 (10)
H22A1.38830.41910.63430.107*
H22B1.43970.38140.54830.107*
H22C1.35320.30210.61170.107*
C231.2078 (5)0.4660 (2)0.4928 (2)0.0730 (11)
H23A1.23910.51890.53990.110*
H23B1.10500.46440.45990.110*
H23C1.28630.47920.45330.110*
C241.0297 (3)0.3108 (2)0.30455 (17)0.0358 (6)
H240.93470.31060.26810.043*
C251.1823 (3)0.3496 (2)0.26884 (17)0.0349 (6)
C261.2355 (3)0.4487 (2)0.24285 (17)0.0373 (6)
C271.3818 (3)0.4862 (2)0.21383 (18)0.0410 (7)
H271.41510.55290.19700.049*
C281.4770 (3)0.4232 (2)0.21036 (17)0.0406 (7)
C291.4252 (3)0.3228 (2)0.23034 (19)0.0455 (7)
H291.48810.27980.22460.055*
C301.2782 (3)0.2868 (2)0.25912 (18)0.0432 (7)
H301.24260.21880.27230.052*
Cl11.16567 (13)0.36529 (9)0.02980 (7)0.0868 (3)
Cl20.58804 (9)0.34674 (7)0.02462 (6)0.0630 (2)
Cl31.66675 (9)0.47063 (7)0.18178 (6)0.0626 (2)
Cl41.11859 (10)0.52998 (7)0.24962 (6)0.0644 (2)
Cl50.73853 (7)0.02334 (5)0.60279 (5)0.04108 (17)
Co10.50000.00000.50000.02659 (13)
N10.6509 (2)0.12807 (17)0.28403 (14)0.0363 (4)
N20.5432 (2)0.08524 (16)0.39304 (14)0.0367 (4)
C140.4351 (3)0.1547 (2)0.33316 (18)0.0417 (4)
H140.32740.18000.33940.050*
N40.6547 (2)0.13667 (16)0.45758 (14)0.0335 (5)
N50.7373 (3)0.26797 (19)0.37297 (18)0.0511 (7)
N60.8632 (2)0.23515 (15)0.40909 (14)0.0319 (5)
O10.9452 (2)0.03136 (14)0.27492 (13)0.0439 (5)
H11.02670.01810.29800.066*
O21.1451 (2)0.18421 (14)0.49524 (13)0.0437 (5)
H2A1.18070.14850.46500.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.062 (2)0.0462 (18)0.0542 (19)0.0276 (15)0.0284 (16)0.0082 (15)
C20.065 (2)0.0433 (17)0.0407 (16)0.0158 (15)0.0172 (15)0.0033 (13)
C30.0473 (16)0.0380 (16)0.0386 (16)0.0117 (13)0.0122 (13)0.0010 (12)
C40.0451 (15)0.0346 (15)0.0301 (14)0.0150 (12)0.0106 (12)0.0042 (11)
C50.0500 (17)0.0476 (17)0.0355 (15)0.0212 (14)0.0052 (13)0.0014 (13)
C60.0470 (17)0.0503 (18)0.0540 (19)0.0226 (14)0.0128 (15)0.0096 (15)
C70.0412 (15)0.0382 (15)0.0307 (14)0.0095 (12)0.0103 (12)0.0022 (12)
C80.0315 (13)0.0412 (15)0.0228 (12)0.0142 (11)0.0040 (10)0.0001 (11)
C90.0371 (14)0.0386 (15)0.0346 (14)0.0125 (12)0.0092 (12)0.0005 (12)
C100.064 (2)0.0461 (18)0.0389 (17)0.0189 (15)0.0023 (15)0.0089 (14)
C110.076 (2)0.075 (3)0.076 (2)0.045 (2)0.003 (2)0.016 (2)
C120.109 (3)0.063 (2)0.076 (3)0.019 (2)0.028 (2)0.031 (2)
C130.116 (3)0.074 (3)0.046 (2)0.031 (2)0.021 (2)0.0038 (18)
N30.0373 (6)0.0467 (7)0.0409 (6)0.0086 (5)0.0078 (5)0.0036 (5)
C150.0346 (6)0.0391 (7)0.0348 (6)0.0112 (5)0.0073 (5)0.0007 (5)
C160.0280 (14)0.0559 (19)0.069 (2)0.0161 (13)0.0152 (14)0.0278 (16)
C170.0295 (13)0.0343 (14)0.0348 (14)0.0074 (11)0.0075 (11)0.0082 (11)
C180.0279 (12)0.0274 (13)0.0369 (14)0.0063 (10)0.0102 (11)0.0051 (11)
C190.0288 (13)0.0374 (15)0.0384 (15)0.0106 (11)0.0124 (11)0.0079 (12)
C200.0435 (16)0.0433 (17)0.0398 (16)0.0090 (13)0.0030 (13)0.0003 (13)
C210.065 (2)0.072 (2)0.0461 (18)0.0189 (18)0.0133 (16)0.0139 (16)
C220.053 (2)0.093 (3)0.055 (2)0.0075 (19)0.0067 (17)0.0029 (19)
C230.097 (3)0.0367 (19)0.074 (2)0.0077 (18)0.003 (2)0.0073 (17)
C240.0313 (13)0.0375 (15)0.0368 (15)0.0056 (11)0.0077 (11)0.0090 (12)
C250.0324 (13)0.0406 (16)0.0297 (14)0.0063 (12)0.0075 (11)0.0061 (12)
C260.0359 (14)0.0423 (16)0.0337 (14)0.0103 (12)0.0074 (12)0.0082 (12)
C270.0389 (15)0.0401 (16)0.0393 (15)0.0019 (13)0.0105 (12)0.0087 (13)
C280.0319 (14)0.0547 (18)0.0317 (14)0.0048 (13)0.0104 (12)0.0033 (13)
C290.0462 (16)0.0555 (19)0.0415 (16)0.0216 (14)0.0148 (13)0.0054 (14)
C300.0489 (16)0.0409 (16)0.0423 (16)0.0119 (13)0.0165 (13)0.0103 (13)
Cl10.0909 (7)0.0960 (8)0.0971 (7)0.0481 (6)0.0490 (6)0.0096 (6)
Cl20.0487 (4)0.0748 (6)0.0564 (5)0.0078 (4)0.0031 (4)0.0177 (4)
Cl30.0381 (4)0.0823 (6)0.0635 (5)0.0041 (4)0.0239 (4)0.0016 (4)
Cl40.0627 (5)0.0574 (5)0.0889 (6)0.0315 (4)0.0316 (5)0.0308 (5)
Cl50.0340 (3)0.0487 (4)0.0436 (4)0.0183 (3)0.0032 (3)0.0068 (3)
Co10.0233 (2)0.0310 (3)0.0276 (3)0.00848 (19)0.00932 (19)0.0044 (2)
N10.0343 (6)0.0401 (6)0.0350 (6)0.0107 (5)0.0075 (5)0.0014 (5)
N20.0346 (6)0.0403 (6)0.0362 (6)0.0117 (5)0.0078 (5)0.0000 (5)
C140.0371 (6)0.0458 (7)0.0410 (7)0.0098 (6)0.0079 (5)0.0021 (6)
N40.0295 (11)0.0347 (12)0.0377 (12)0.0089 (9)0.0111 (9)0.0078 (10)
N50.0357 (13)0.0525 (16)0.0721 (18)0.0185 (11)0.0166 (12)0.0324 (14)
N60.0273 (10)0.0316 (12)0.0383 (12)0.0088 (9)0.0095 (9)0.0095 (10)
O10.0360 (10)0.0456 (12)0.0459 (12)0.0106 (9)0.0032 (9)0.0067 (9)
O20.0482 (11)0.0436 (11)0.0501 (12)0.0257 (9)0.0159 (9)0.0145 (9)
Geometric parameters (Å, º) top
C1—C61.367 (4)C18—C241.319 (3)
C1—C21.373 (4)C18—N61.439 (3)
C1—Cl11.737 (3)C18—C191.513 (3)
C2—C31.376 (4)C19—O21.424 (3)
C2—H20.9300C19—C201.543 (4)
C3—C41.389 (4)C19—H190.9800
C3—Cl21.731 (3)C20—C211.525 (4)
C4—C51.387 (4)C20—C221.527 (4)
C4—C71.474 (3)C20—C231.529 (4)
C5—C61.378 (4)C21—H21A0.9600
C5—H50.9300C21—H21B0.9600
C6—H60.9300C21—H21C0.9600
C7—C81.320 (4)C22—H22A0.9600
C7—H70.9300C22—H22B0.9600
C8—N11.441 (3)C22—H22C0.9600
C8—C91.509 (4)C23—H23A0.9600
C9—O11.427 (3)C23—H23B0.9600
C9—C101.544 (4)C23—H23C0.9600
C9—H90.9800C24—C251.481 (3)
C10—C111.525 (4)C24—H240.9300
C10—C121.529 (5)C25—C261.389 (4)
C10—C131.534 (4)C25—C301.389 (4)
C11—H11A0.9600C26—C271.382 (4)
C11—H11B0.9600C26—Cl41.733 (3)
C11—H11C0.9600C27—C281.373 (4)
C12—H12A0.9600C27—H270.9300
C12—H12B0.9600C28—C291.374 (4)
C12—H12C0.9600C28—Cl31.731 (3)
C13—H13A0.9600C29—C301.383 (4)
C13—H13B0.9600C29—H290.9300
C13—H13C0.9600C30—H300.9300
N3—C141.309 (3)Cl5—Co12.5227 (8)
N3—N11.365 (3)Co1—N22.126 (2)
C15—N21.315 (3)Co1—N2i2.126 (2)
C15—N11.327 (3)Co1—N4i2.147 (2)
C15—H150.9300Co1—N42.147 (2)
C16—N51.309 (3)Co1—Cl5i2.5227 (8)
C16—N41.344 (3)N2—C141.352 (3)
C16—H160.9300C14—H140.9300
C17—N41.321 (3)N5—N61.359 (3)
C17—N61.328 (3)O1—H10.8200
C17—H170.9300O2—H2A0.8200
C6—C1—C2121.9 (3)C21—C20—C19112.8 (2)
C6—C1—Cl1119.8 (2)C22—C20—C19106.4 (3)
C2—C1—Cl1118.3 (2)C23—C20—C19109.3 (2)
C1—C2—C3118.5 (3)C20—C21—H21A109.5
C1—C2—H2120.7C20—C21—H21B109.5
C3—C2—H2120.7H21A—C21—H21B109.5
C2—C3—C4121.9 (3)C20—C21—H21C109.5
C2—C3—Cl2118.8 (2)H21A—C21—H21C109.5
C4—C3—Cl2119.3 (2)H21B—C21—H21C109.5
C5—C4—C3117.1 (2)C20—C22—H22A109.5
C5—C4—C7122.0 (2)C20—C22—H22B109.5
C3—C4—C7120.7 (2)H22A—C22—H22B109.5
C6—C5—C4122.0 (3)C20—C22—H22C109.5
C6—C5—H5119.0H22A—C22—H22C109.5
C4—C5—H5119.0H22B—C22—H22C109.5
C1—C6—C5118.5 (3)C20—C23—H23A109.5
C1—C6—H6120.7C20—C23—H23B109.5
C5—C6—H6120.7H23A—C23—H23B109.5
C8—C7—C4126.8 (2)C20—C23—H23C109.5
C8—C7—H7116.6H23A—C23—H23C109.5
C4—C7—H7116.6H23B—C23—H23C109.5
C7—C8—N1117.2 (2)C18—C24—C25123.9 (2)
C7—C8—C9126.6 (2)C18—C24—H24118.0
N1—C8—C9116.1 (2)C25—C24—H24118.0
O1—C9—C8111.5 (2)C26—C25—C30117.1 (2)
O1—C9—C10108.0 (2)C26—C25—C24122.3 (2)
C8—C9—C10115.1 (2)C30—C25—C24120.6 (2)
O1—C9—H9107.3C27—C26—C25122.1 (3)
C8—C9—H9107.3C27—C26—Cl4118.3 (2)
C10—C9—H9107.3C25—C26—Cl4119.6 (2)
C11—C10—C12108.8 (3)C28—C27—C26118.8 (3)
C11—C10—C13110.4 (3)C28—C27—H27120.6
C12—C10—C13108.9 (3)C26—C27—H27120.6
C11—C10—C9112.4 (2)C27—C28—C29121.1 (2)
C12—C10—C9107.2 (3)C27—C28—Cl3119.7 (2)
C13—C10—C9109.1 (3)C29—C28—Cl3119.1 (2)
C10—C11—H11A109.5C28—C29—C30119.0 (3)
C10—C11—H11B109.5C28—C29—H29120.5
H11A—C11—H11B109.5C30—C29—H29120.5
C10—C11—H11C109.5C29—C30—C25121.7 (3)
H11A—C11—H11C109.5C29—C30—H30119.2
H11B—C11—H11C109.5C25—C30—H30119.2
C10—C12—H12A109.5N2—Co1—N2i180.0
C10—C12—H12B109.5N2—Co1—N4i90.22 (8)
H12A—C12—H12B109.5N2i—Co1—N4i89.78 (8)
C10—C12—H12C109.5N2—Co1—N489.78 (8)
H12A—C12—H12C109.5N2i—Co1—N490.22 (8)
H12B—C12—H12C109.5N4i—Co1—N4180.00 (8)
C10—C13—H13A109.5N2—Co1—Cl5i88.23 (6)
C10—C13—H13B109.5N2i—Co1—Cl5i91.77 (6)
H13A—C13—H13B109.5N4i—Co1—Cl5i89.15 (6)
C10—C13—H13C109.5N4—Co1—Cl5i90.85 (6)
H13A—C13—H13C109.5N2—Co1—Cl591.77 (6)
H13B—C13—H13C109.5N2i—Co1—Cl588.23 (6)
C14—N3—N1102.1 (2)N4i—Co1—Cl590.85 (6)
N2—C15—N1110.7 (2)N4—Co1—Cl589.15 (6)
N2—C15—H15124.6Cl5i—Co1—Cl5180.00 (3)
N1—C15—H15124.6C15—N1—N3109.4 (2)
N5—C16—N4115.2 (2)C15—N1—C8129.1 (2)
N5—C16—H16122.4N3—N1—C8121.5 (2)
N4—C16—H16122.4C15—N2—C14102.5 (2)
N4—C17—N6110.5 (2)C15—N2—Co1128.29 (18)
N4—C17—H17124.8C14—N2—Co1128.41 (17)
N6—C17—H17124.8N3—C14—N2115.2 (2)
C24—C18—N6118.0 (2)N3—C14—H14122.4
C24—C18—C19125.8 (2)N2—C14—H14122.4
N6—C18—C19116.1 (2)C17—N4—C16102.6 (2)
O2—C19—C18111.8 (2)C17—N4—Co1126.15 (17)
O2—C19—C20108.6 (2)C16—N4—Co1129.29 (17)
C18—C19—C20115.3 (2)C16—N5—N6102.5 (2)
O2—C19—H19106.9C17—N6—N5109.3 (2)
C18—C19—H19106.9C17—N6—C18129.1 (2)
C20—C19—H19106.9N5—N6—C18121.3 (2)
C21—C20—C22109.1 (3)C9—O1—H1109.5
C21—C20—C23109.9 (3)C19—O2—H2A109.5
C22—C20—C23109.3 (3)
C6—C1—C2—C30.4 (5)Cl3—C28—C29—C30175.6 (2)
Cl1—C1—C2—C3179.5 (2)C28—C29—C30—C250.4 (4)
C1—C2—C3—C40.0 (4)C26—C25—C30—C294.1 (4)
C1—C2—C3—Cl2179.5 (2)C24—C25—C30—C29176.6 (3)
C2—C3—C4—C50.4 (4)N2—C15—N1—N31.7 (3)
Cl2—C3—C4—C5179.1 (2)N2—C15—N1—C8179.8 (2)
C2—C3—C4—C7175.2 (3)C14—N3—N1—C151.1 (3)
Cl2—C3—C4—C75.3 (4)C14—N3—N1—C8179.4 (2)
C3—C4—C5—C60.5 (4)C7—C8—N1—C15133.4 (3)
C7—C4—C5—C6175.1 (3)C9—C8—N1—C1550.9 (4)
C2—C1—C6—C50.4 (5)C7—C8—N1—N344.5 (3)
Cl1—C1—C6—C5179.5 (2)C9—C8—N1—N3131.1 (2)
C4—C5—C6—C10.0 (4)N1—C15—N2—C141.5 (3)
C5—C4—C7—C860.7 (4)N1—C15—N2—Co1168.98 (17)
C3—C4—C7—C8123.9 (3)N2i—Co1—N2—C1546 (100)
C4—C7—C8—N1179.2 (2)N4i—Co1—N2—C15143.4 (2)
C4—C7—C8—C95.7 (4)N4—Co1—N2—C1536.6 (2)
C7—C8—C9—O1134.4 (3)Cl5i—Co1—N2—C15127.4 (2)
N1—C8—C9—O150.5 (3)Cl5—Co1—N2—C1552.6 (2)
C7—C8—C9—C10102.1 (3)N2i—Co1—N2—C14122 (100)
N1—C8—C9—C1073.1 (3)N4i—Co1—N2—C1448.5 (2)
O1—C9—C10—C1154.3 (3)N4—Co1—N2—C14131.5 (2)
C8—C9—C10—C1171.1 (3)Cl5i—Co1—N2—C1440.7 (2)
O1—C9—C10—C1265.2 (3)Cl5—Co1—N2—C14139.3 (2)
C8—C9—C10—C12169.4 (3)N1—N3—C14—N20.1 (3)
O1—C9—C10—C13177.1 (3)C15—N2—C14—N30.8 (3)
C8—C9—C10—C1351.7 (3)Co1—N2—C14—N3169.63 (19)
C24—C18—C19—O2131.9 (3)N6—C17—N4—C160.7 (3)
N6—C18—C19—O250.7 (3)N6—C17—N4—Co1164.63 (16)
C24—C18—C19—C20103.3 (3)N5—C16—N4—C170.4 (4)
N6—C18—C19—C2074.0 (3)N5—C16—N4—Co1164.3 (2)
O2—C19—C20—C2155.1 (3)N2—Co1—N4—C1766.5 (2)
C18—C19—C20—C2171.2 (3)N2i—Co1—N4—C17113.5 (2)
O2—C19—C20—C2264.4 (3)N4i—Co1—N4—C17151 (100)
C18—C19—C20—C22169.2 (2)Cl5i—Co1—N4—C17154.7 (2)
O2—C19—C20—C23177.7 (2)Cl5—Co1—N4—C1725.3 (2)
C18—C19—C20—C2351.4 (3)N2—Co1—N4—C1694.9 (2)
N6—C18—C24—C25176.3 (2)N2i—Co1—N4—C1685.1 (2)
C19—C18—C24—C256.3 (4)N4i—Co1—N4—C1648 (100)
C18—C24—C25—C26119.7 (3)Cl5i—Co1—N4—C166.7 (2)
C18—C24—C25—C3061.0 (4)Cl5—Co1—N4—C16173.3 (2)
C30—C25—C26—C274.0 (4)N4—C16—N5—N60.1 (4)
C24—C25—C26—C27176.7 (2)N4—C17—N6—N50.8 (3)
C30—C25—C26—Cl4177.9 (2)N4—C17—N6—C18173.2 (2)
C24—C25—C26—Cl41.5 (4)C16—N5—N6—C170.5 (3)
C25—C26—C27—C280.2 (4)C16—N5—N6—C18174.0 (2)
Cl4—C26—C27—C28178.4 (2)C24—C18—N6—C17144.7 (3)
C26—C27—C28—C293.7 (4)C19—C18—N6—C1737.7 (4)
C26—C27—C28—Cl3175.5 (2)C24—C18—N6—N528.7 (4)
C27—C28—C29—C303.6 (4)C19—C18—N6—N5148.9 (2)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cl5ii0.822.353.136 (2)161
O2—H2A···Cl5ii0.822.323.128 (2)169
Symmetry code: (ii) x+2, y, z+1.

Experimental details

Crystal data
Chemical formula[CoCl2(C15H17Cl2N3O)4]
Mr1434.69
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.800 (2), 13.729 (4), 15.145 (4)
α, β, γ (°)90.918 (3), 98.560 (3), 106.775 (3)
V3)1729.0 (8)
Z1
Radiation typeMo Kα
µ (mm1)0.69
Crystal size (mm)0.25 × 0.21 × 0.13
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.847, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
12895, 6356, 4764
Rint0.027
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.098, 1.02
No. of reflections6356
No. of parameters402
No. of restraints70
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.53

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cl5i0.822.353.136 (2)161.2
O2—H2A···Cl5i0.822.323.128 (2)169.0
Symmetry code: (i) x+2, y, z+1.
 

Acknowledgements

This work was supported by the Foundation of Educational Department of Jiangxi Province (GJJ11079) and the Natural Science Youth Foundation of Jiangxi Agricultural University, China (09003319 and 09003321).

References

First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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First citationGao, J.-S., Ma, D.-S., Ma, Z.-G. & Chen, G.-R. (2001). Chin. J. Mol. Sci. 17, 1, 17–22.  Google Scholar
First citationHuang, X.-G., Zhao, A.-J., Liu, X.-G., Zhou, D.-H. & Zeng, B. (2003). Acta Agric. Univ. Jiangxiensis, 25, 277–288.  Google Scholar
First citationSheldrick, G. M. (2007). SADABS, University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSumitomo Chemical. (1984). Jpn Pestic. Soc. 6, 229–236.  Google Scholar
First citationXia, H.-Y., Duan, Z.-X., Tu, Y.-M. & Liu, J.-H. (2001). Chin. J. Pestic. 40, 12, 12–14.  Google Scholar
First citationXiong, Z.-Q., Chen, J.-Z., Wen, S.-H. & Nie, X.-L. (2010). Acta Cryst. E66, o3278.  CrossRef IUCr Journals Google Scholar

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