Dichloridotetra­kis­(diniconazole)cobalt(II)

Liu, C.-X.; Song, X.-Y.; Liu, Q.; Nie, X.-L.; Wen, S.-H.

doi:10.1107/S1600536811031291

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1214

doi:10.1107/S1600536811031291

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Dichloridotetrakis(diniconazole)cobalt(II)

Chang-Xiang Liu,^a Xiu-Ying Song,^a Qian Liu,^a Xu-Liang Nie ^a ^* and Shi-He Wen ^a

^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 Co^II 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 ); 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

Crystal data

[CoCl₂(C₁₅H₁₇Cl₂N₃O)₄]
M_r = 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 ) T_min = 0.847, T_max = 0.916
12895 measured reflections
6356 independent reflections
4764 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811031291/xu5277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031291/xu5277Isup2.hkl

checkCIF report

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.

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

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and displacement ellipsoids at the 40% probability level.
	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
M_r = 1434.69	F(000) = 741
Triclinic, P1	D_x = 1.378 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.800 (2) Å	Cell parameters from 5326 reflections
b = 13.729 (4) Å	θ = 2.5–27.7°
c = 15.145 (4) Å	µ = 0.69 mm⁻¹
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 tube	4764 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
T_min = 0.847, T_max = 0.916	k = −16→16
12895 measured reflections	l = −18→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0391P)² + 0.9781P] where P = (F_o² + 2F_c²)/3
6356 reflections	(Δ/σ)_max < 0.001
402 parameters	Δρ_max = 0.58 e Å⁻³
70 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[CoCl₂(C₁₅H₁₇Cl₂N₃O)₄]	γ = 106.775 (3)°
M_r = 1434.69	V = 1729.0 (8) Å³
Triclinic, P1	Z = 1
a = 8.800 (2) Å	Mo Kα radiation
b = 13.729 (4) Å	µ = 0.69 mm⁻¹
c = 15.145 (4) Å	T = 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)
T_min = 0.847, T_max = 0.916	R_int = 0.027
12895 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	70 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.02	Δρ_max = 0.58 e Å⁻³
6356 reflections	Δρ_min = −0.53 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	1.0494 (4)	−0.3225 (2)	0.0361 (2)	0.0497 (8)
C2	0.8863 (4)	−0.3484 (2)	0.0079 (2)	0.0489 (7)
H2	0.8396	−0.3873	−0.0453	0.059*
C3	0.7935 (3)	−0.3154 (2)	0.06012 (18)	0.0409 (7)
C4	0.8601 (3)	−0.2571 (2)	0.13991 (17)	0.0354 (6)
C5	1.0255 (3)	−0.2327 (2)	0.16483 (19)	0.0431 (7)
H5	1.0734	−0.1933	0.2177	0.052*
C6	1.1210 (4)	−0.2648 (2)	0.1137 (2)	0.0481 (7)
H6	1.2317	−0.2477	0.1316	0.058*
C7	0.7567 (3)	−0.2295 (2)	0.19802 (17)	0.0367 (6)
H7	0.6785	−0.2831	0.2166	0.044*
C8	0.7633 (3)	−0.1368 (2)	0.22641 (16)	0.0311 (6)
C9	0.8686 (3)	−0.0379 (2)	0.19926 (17)	0.0362 (6)
H9	0.9536	−0.0539	0.1721	0.043*
C10	0.7825 (4)	0.0182 (2)	0.13025 (19)	0.0497 (8)
C11	0.6677 (4)	0.0643 (3)	0.1702 (3)	0.0714 (10)
H11A	0.7229	0.1041	0.2244	0.107*
H11B	0.5777	0.0107	0.1831	0.107*
H11C	0.6303	0.1072	0.1282	0.107*
C12	0.9126 (5)	0.1039 (3)	0.0983 (3)	0.0819 (12)
H12A	0.9661	0.1530	0.1472	0.123*
H12B	0.8641	0.1365	0.0511	0.123*
H12C	0.9893	0.0762	0.0764	0.123*
C13	0.6918 (5)	−0.0564 (3)	0.0503 (2)	0.0814 (12)
H13A	0.6532	−0.0197	0.0029	0.122*
H13B	0.6024	−0.1063	0.0683	0.122*
H13C	0.7629	−0.0899	0.0296	0.122*
N3	0.4927 (3)	−0.18374 (18)	0.26583 (15)	0.0424 (4)
C15	0.6774 (3)	−0.0721 (2)	0.36012 (17)	0.0359 (4)
H15	0.7771	−0.0294	0.3865	0.043*
C16	0.6166 (3)	0.2063 (2)	0.4043 (2)	0.0490 (8)
H16	0.5121	0.2104	0.3907	0.059*
C17	0.8114 (3)	0.15788 (19)	0.45944 (17)	0.0330 (6)
H17	0.8764	0.1235	0.4915	0.040*
C18	1.0204 (3)	0.27636 (18)	0.38500 (17)	0.0305 (6)
C19	1.1615 (3)	0.27996 (19)	0.45688 (17)	0.0339 (6)
H19	1.2570	0.2944	0.4276	0.041*
C20	1.1966 (3)	0.3632 (2)	0.53304 (19)	0.0434 (7)
C21	1.0705 (4)	0.3406 (3)	0.5948 (2)	0.0609 (9)
H21A	1.0569	0.2734	0.6154	0.091*
H21B	0.9701	0.3448	0.5628	0.091*
H21C	1.1050	0.3896	0.6452	0.091*
C22	1.3596 (4)	0.3668 (3)	0.5869 (2)	0.0714 (10)
H22A	1.3883	0.4191	0.6343	0.107*
H22B	1.4397	0.3814	0.5483	0.107*
H22C	1.3532	0.3021	0.6117	0.107*
C23	1.2078 (5)	0.4660 (2)	0.4928 (2)	0.0730 (11)
H23A	1.2391	0.5189	0.5399	0.110*
H23B	1.1050	0.4644	0.4599	0.110*
H23C	1.2863	0.4792	0.4533	0.110*
C24	1.0297 (3)	0.3108 (2)	0.30455 (17)	0.0358 (6)
H24	0.9347	0.3106	0.2681	0.043*
C25	1.1823 (3)	0.3496 (2)	0.26884 (17)	0.0349 (6)
C26	1.2355 (3)	0.4487 (2)	0.24285 (17)	0.0373 (6)
C27	1.3818 (3)	0.4862 (2)	0.21383 (18)	0.0410 (7)
H27	1.4151	0.5529	0.1970	0.049*
C28	1.4770 (3)	0.4232 (2)	0.21036 (17)	0.0406 (7)
C29	1.4252 (3)	0.3228 (2)	0.23034 (19)	0.0455 (7)
H29	1.4881	0.2798	0.2246	0.055*
C30	1.2782 (3)	0.2868 (2)	0.25912 (18)	0.0432 (7)
H30	1.2426	0.2188	0.2723	0.052*
Cl1	1.16567 (13)	−0.36529 (9)	−0.02980 (7)	0.0868 (3)
Cl2	0.58804 (9)	−0.34674 (7)	0.02462 (6)	0.0630 (2)
Cl3	1.66675 (9)	0.47063 (7)	0.18178 (6)	0.0626 (2)
Cl4	1.11859 (10)	0.52998 (7)	0.24962 (6)	0.0644 (2)
Cl5	0.73853 (7)	−0.02334 (5)	0.60279 (5)	0.04108 (17)
Co1	0.5000	0.0000	0.5000	0.02659 (13)
N1	0.6509 (2)	−0.12807 (17)	0.28403 (14)	0.0363 (4)
N2	0.5432 (2)	−0.08524 (16)	0.39304 (14)	0.0367 (4)
C14	0.4351 (3)	−0.1547 (2)	0.33316 (18)	0.0417 (4)
H14	0.3274	−0.1800	0.3394	0.050*
N4	0.6547 (2)	0.13667 (16)	0.45758 (14)	0.0335 (5)
N5	0.7373 (3)	0.26797 (19)	0.37297 (18)	0.0511 (7)
N6	0.8632 (2)	0.23515 (15)	0.40909 (14)	0.0319 (5)
O1	0.9452 (2)	0.03136 (14)	0.27492 (13)	0.0439 (5)
H1	1.0267	0.0181	0.2980	0.066*
O2	1.1451 (2)	0.18421 (14)	0.49524 (13)	0.0437 (5)
H2A	1.1807	0.1485	0.4650	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.062 (2)	0.0462 (18)	0.0542 (19)	0.0276 (15)	0.0284 (16)	0.0082 (15)
C2	0.065 (2)	0.0433 (17)	0.0407 (16)	0.0158 (15)	0.0172 (15)	−0.0033 (13)
C3	0.0473 (16)	0.0380 (16)	0.0386 (16)	0.0117 (13)	0.0122 (13)	0.0010 (12)
C4	0.0451 (15)	0.0346 (15)	0.0301 (14)	0.0150 (12)	0.0106 (12)	0.0042 (11)
C5	0.0500 (17)	0.0476 (17)	0.0355 (15)	0.0212 (14)	0.0052 (13)	0.0014 (13)
C6	0.0470 (17)	0.0503 (18)	0.0540 (19)	0.0226 (14)	0.0128 (15)	0.0096 (15)
C7	0.0412 (15)	0.0382 (15)	0.0307 (14)	0.0095 (12)	0.0103 (12)	0.0022 (12)
C8	0.0315 (13)	0.0412 (15)	0.0228 (12)	0.0142 (11)	0.0040 (10)	0.0001 (11)
C9	0.0371 (14)	0.0386 (15)	0.0346 (14)	0.0125 (12)	0.0092 (12)	−0.0005 (12)
C10	0.064 (2)	0.0461 (18)	0.0389 (17)	0.0189 (15)	0.0023 (15)	0.0089 (14)
C11	0.076 (2)	0.075 (3)	0.076 (2)	0.045 (2)	0.003 (2)	0.016 (2)
C12	0.109 (3)	0.063 (2)	0.076 (3)	0.019 (2)	0.028 (2)	0.031 (2)
C13	0.116 (3)	0.074 (3)	0.046 (2)	0.031 (2)	−0.021 (2)	0.0038 (18)
N3	0.0373 (6)	0.0467 (7)	0.0409 (6)	0.0086 (5)	0.0078 (5)	−0.0036 (5)
C15	0.0346 (6)	0.0391 (7)	0.0348 (6)	0.0112 (5)	0.0073 (5)	−0.0007 (5)
C16	0.0280 (14)	0.0559 (19)	0.069 (2)	0.0161 (13)	0.0152 (14)	0.0278 (16)
C17	0.0295 (13)	0.0343 (14)	0.0348 (14)	0.0074 (11)	0.0075 (11)	0.0082 (11)
C18	0.0279 (12)	0.0274 (13)	0.0369 (14)	0.0063 (10)	0.0102 (11)	0.0051 (11)
C19	0.0288 (13)	0.0374 (15)	0.0384 (15)	0.0106 (11)	0.0124 (11)	0.0079 (12)
C20	0.0435 (16)	0.0433 (17)	0.0398 (16)	0.0090 (13)	0.0030 (13)	0.0003 (13)
C21	0.065 (2)	0.072 (2)	0.0461 (18)	0.0189 (18)	0.0133 (16)	−0.0139 (16)
C22	0.053 (2)	0.093 (3)	0.055 (2)	0.0075 (19)	−0.0067 (17)	−0.0029 (19)
C23	0.097 (3)	0.0367 (19)	0.074 (2)	0.0077 (18)	0.003 (2)	−0.0073 (17)
C24	0.0313 (13)	0.0375 (15)	0.0368 (15)	0.0056 (11)	0.0077 (11)	0.0090 (12)
C25	0.0324 (13)	0.0406 (16)	0.0297 (14)	0.0063 (12)	0.0075 (11)	0.0061 (12)
C26	0.0359 (14)	0.0423 (16)	0.0337 (14)	0.0103 (12)	0.0074 (12)	0.0082 (12)
C27	0.0389 (15)	0.0401 (16)	0.0393 (15)	0.0019 (13)	0.0105 (12)	0.0087 (13)
C28	0.0319 (14)	0.0547 (18)	0.0317 (14)	0.0048 (13)	0.0104 (12)	0.0033 (13)
C29	0.0462 (16)	0.0555 (19)	0.0415 (16)	0.0216 (14)	0.0148 (13)	0.0054 (14)
C30	0.0489 (16)	0.0409 (16)	0.0423 (16)	0.0119 (13)	0.0165 (13)	0.0103 (13)
Cl1	0.0909 (7)	0.0960 (8)	0.0971 (7)	0.0481 (6)	0.0490 (6)	−0.0096 (6)
Cl2	0.0487 (4)	0.0748 (6)	0.0564 (5)	0.0078 (4)	0.0031 (4)	−0.0177 (4)
Cl3	0.0381 (4)	0.0823 (6)	0.0635 (5)	0.0041 (4)	0.0239 (4)	0.0016 (4)
Cl4	0.0627 (5)	0.0574 (5)	0.0889 (6)	0.0315 (4)	0.0316 (5)	0.0308 (5)
Cl5	0.0340 (3)	0.0487 (4)	0.0436 (4)	0.0183 (3)	0.0032 (3)	0.0068 (3)
Co1	0.0233 (2)	0.0310 (3)	0.0276 (3)	0.00848 (19)	0.00932 (19)	0.0044 (2)
N1	0.0343 (6)	0.0401 (6)	0.0350 (6)	0.0107 (5)	0.0075 (5)	−0.0014 (5)
N2	0.0346 (6)	0.0403 (6)	0.0362 (6)	0.0117 (5)	0.0078 (5)	0.0000 (5)
C14	0.0371 (6)	0.0458 (7)	0.0410 (7)	0.0098 (6)	0.0079 (5)	−0.0021 (6)
N4	0.0295 (11)	0.0347 (12)	0.0377 (12)	0.0089 (9)	0.0111 (9)	0.0078 (10)
N5	0.0357 (13)	0.0525 (16)	0.0721 (18)	0.0185 (11)	0.0166 (12)	0.0324 (14)
N6	0.0273 (10)	0.0316 (12)	0.0383 (12)	0.0088 (9)	0.0095 (9)	0.0095 (10)
O1	0.0360 (10)	0.0456 (12)	0.0459 (12)	0.0106 (9)	−0.0032 (9)	−0.0067 (9)
O2	0.0482 (11)	0.0436 (11)	0.0501 (12)	0.0257 (9)	0.0159 (9)	0.0145 (9)

Geometric parameters (Å, º) top

C1—C6	1.367 (4)	C18—C24	1.319 (3)
C1—C2	1.373 (4)	C18—N6	1.439 (3)
C1—Cl1	1.737 (3)	C18—C19	1.513 (3)
C2—C3	1.376 (4)	C19—O2	1.424 (3)
C2—H2	0.9300	C19—C20	1.543 (4)
C3—C4	1.389 (4)	C19—H19	0.9800
C3—Cl2	1.731 (3)	C20—C21	1.525 (4)
C4—C5	1.387 (4)	C20—C22	1.527 (4)
C4—C7	1.474 (3)	C20—C23	1.529 (4)
C5—C6	1.378 (4)	C21—H21A	0.9600
C5—H5	0.9300	C21—H21B	0.9600
C6—H6	0.9300	C21—H21C	0.9600
C7—C8	1.320 (4)	C22—H22A	0.9600
C7—H7	0.9300	C22—H22B	0.9600
C8—N1	1.441 (3)	C22—H22C	0.9600
C8—C9	1.509 (4)	C23—H23A	0.9600
C9—O1	1.427 (3)	C23—H23B	0.9600
C9—C10	1.544 (4)	C23—H23C	0.9600
C9—H9	0.9800	C24—C25	1.481 (3)
C10—C11	1.525 (4)	C24—H24	0.9300
C10—C12	1.529 (5)	C25—C26	1.389 (4)
C10—C13	1.534 (4)	C25—C30	1.389 (4)
C11—H11A	0.9600	C26—C27	1.382 (4)
C11—H11B	0.9600	C26—Cl4	1.733 (3)
C11—H11C	0.9600	C27—C28	1.373 (4)
C12—H12A	0.9600	C27—H27	0.9300
C12—H12B	0.9600	C28—C29	1.374 (4)
C12—H12C	0.9600	C28—Cl3	1.731 (3)
C13—H13A	0.9600	C29—C30	1.383 (4)
C13—H13B	0.9600	C29—H29	0.9300
C13—H13C	0.9600	C30—H30	0.9300
N3—C14	1.309 (3)	Cl5—Co1	2.5227 (8)
N3—N1	1.365 (3)	Co1—N2	2.126 (2)
C15—N2	1.315 (3)	Co1—N2ⁱ	2.126 (2)
C15—N1	1.327 (3)	Co1—N4ⁱ	2.147 (2)
C15—H15	0.9300	Co1—N4	2.147 (2)
C16—N5	1.309 (3)	Co1—Cl5ⁱ	2.5227 (8)
C16—N4	1.344 (3)	N2—C14	1.352 (3)
C16—H16	0.9300	C14—H14	0.9300
C17—N4	1.321 (3)	N5—N6	1.359 (3)
C17—N6	1.328 (3)	O1—H1	0.8200
C17—H17	0.9300	O2—H2A	0.8200

C6—C1—C2	121.9 (3)	C21—C20—C19	112.8 (2)
C6—C1—Cl1	119.8 (2)	C22—C20—C19	106.4 (3)
C2—C1—Cl1	118.3 (2)	C23—C20—C19	109.3 (2)
C1—C2—C3	118.5 (3)	C20—C21—H21A	109.5
C1—C2—H2	120.7	C20—C21—H21B	109.5
C3—C2—H2	120.7	H21A—C21—H21B	109.5
C2—C3—C4	121.9 (3)	C20—C21—H21C	109.5
C2—C3—Cl2	118.8 (2)	H21A—C21—H21C	109.5
C4—C3—Cl2	119.3 (2)	H21B—C21—H21C	109.5
C5—C4—C3	117.1 (2)	C20—C22—H22A	109.5
C5—C4—C7	122.0 (2)	C20—C22—H22B	109.5
C3—C4—C7	120.7 (2)	H22A—C22—H22B	109.5
C6—C5—C4	122.0 (3)	C20—C22—H22C	109.5
C6—C5—H5	119.0	H22A—C22—H22C	109.5
C4—C5—H5	119.0	H22B—C22—H22C	109.5
C1—C6—C5	118.5 (3)	C20—C23—H23A	109.5
C1—C6—H6	120.7	C20—C23—H23B	109.5
C5—C6—H6	120.7	H23A—C23—H23B	109.5
C8—C7—C4	126.8 (2)	C20—C23—H23C	109.5
C8—C7—H7	116.6	H23A—C23—H23C	109.5
C4—C7—H7	116.6	H23B—C23—H23C	109.5
C7—C8—N1	117.2 (2)	C18—C24—C25	123.9 (2)
C7—C8—C9	126.6 (2)	C18—C24—H24	118.0
N1—C8—C9	116.1 (2)	C25—C24—H24	118.0
O1—C9—C8	111.5 (2)	C26—C25—C30	117.1 (2)
O1—C9—C10	108.0 (2)	C26—C25—C24	122.3 (2)
C8—C9—C10	115.1 (2)	C30—C25—C24	120.6 (2)
O1—C9—H9	107.3	C27—C26—C25	122.1 (3)
C8—C9—H9	107.3	C27—C26—Cl4	118.3 (2)
C10—C9—H9	107.3	C25—C26—Cl4	119.6 (2)
C11—C10—C12	108.8 (3)	C28—C27—C26	118.8 (3)
C11—C10—C13	110.4 (3)	C28—C27—H27	120.6
C12—C10—C13	108.9 (3)	C26—C27—H27	120.6
C11—C10—C9	112.4 (2)	C27—C28—C29	121.1 (2)
C12—C10—C9	107.2 (3)	C27—C28—Cl3	119.7 (2)
C13—C10—C9	109.1 (3)	C29—C28—Cl3	119.1 (2)
C10—C11—H11A	109.5	C28—C29—C30	119.0 (3)
C10—C11—H11B	109.5	C28—C29—H29	120.5
H11A—C11—H11B	109.5	C30—C29—H29	120.5
C10—C11—H11C	109.5	C29—C30—C25	121.7 (3)
H11A—C11—H11C	109.5	C29—C30—H30	119.2
H11B—C11—H11C	109.5	C25—C30—H30	119.2
C10—C12—H12A	109.5	N2—Co1—N2ⁱ	180.0
C10—C12—H12B	109.5	N2—Co1—N4ⁱ	90.22 (8)
H12A—C12—H12B	109.5	N2ⁱ—Co1—N4ⁱ	89.78 (8)
C10—C12—H12C	109.5	N2—Co1—N4	89.78 (8)
H12A—C12—H12C	109.5	N2ⁱ—Co1—N4	90.22 (8)
H12B—C12—H12C	109.5	N4ⁱ—Co1—N4	180.00 (8)
C10—C13—H13A	109.5	N2—Co1—Cl5ⁱ	88.23 (6)
C10—C13—H13B	109.5	N2ⁱ—Co1—Cl5ⁱ	91.77 (6)
H13A—C13—H13B	109.5	N4ⁱ—Co1—Cl5ⁱ	89.15 (6)
C10—C13—H13C	109.5	N4—Co1—Cl5ⁱ	90.85 (6)
H13A—C13—H13C	109.5	N2—Co1—Cl5	91.77 (6)
H13B—C13—H13C	109.5	N2ⁱ—Co1—Cl5	88.23 (6)
C14—N3—N1	102.1 (2)	N4ⁱ—Co1—Cl5	90.85 (6)
N2—C15—N1	110.7 (2)	N4—Co1—Cl5	89.15 (6)
N2—C15—H15	124.6	Cl5ⁱ—Co1—Cl5	180.00 (3)
N1—C15—H15	124.6	C15—N1—N3	109.4 (2)
N5—C16—N4	115.2 (2)	C15—N1—C8	129.1 (2)
N5—C16—H16	122.4	N3—N1—C8	121.5 (2)
N4—C16—H16	122.4	C15—N2—C14	102.5 (2)
N4—C17—N6	110.5 (2)	C15—N2—Co1	128.29 (18)
N4—C17—H17	124.8	C14—N2—Co1	128.41 (17)
N6—C17—H17	124.8	N3—C14—N2	115.2 (2)
C24—C18—N6	118.0 (2)	N3—C14—H14	122.4
C24—C18—C19	125.8 (2)	N2—C14—H14	122.4
N6—C18—C19	116.1 (2)	C17—N4—C16	102.6 (2)
O2—C19—C18	111.8 (2)	C17—N4—Co1	126.15 (17)
O2—C19—C20	108.6 (2)	C16—N4—Co1	129.29 (17)
C18—C19—C20	115.3 (2)	C16—N5—N6	102.5 (2)
O2—C19—H19	106.9	C17—N6—N5	109.3 (2)
C18—C19—H19	106.9	C17—N6—C18	129.1 (2)
C20—C19—H19	106.9	N5—N6—C18	121.3 (2)
C21—C20—C22	109.1 (3)	C9—O1—H1	109.5
C21—C20—C23	109.9 (3)	C19—O2—H2A	109.5
C22—C20—C23	109.3 (3)

C6—C1—C2—C3	−0.4 (5)	Cl3—C28—C29—C30	175.6 (2)
Cl1—C1—C2—C3	179.5 (2)	C28—C29—C30—C25	−0.4 (4)
C1—C2—C3—C4	0.0 (4)	C26—C25—C30—C29	4.1 (4)
C1—C2—C3—Cl2	179.5 (2)	C24—C25—C30—C29	−176.6 (3)
C2—C3—C4—C5	0.4 (4)	N2—C15—N1—N3	−1.7 (3)
Cl2—C3—C4—C5	−179.1 (2)	N2—C15—N1—C8	−179.8 (2)
C2—C3—C4—C7	−175.2 (3)	C14—N3—N1—C15	1.1 (3)
Cl2—C3—C4—C7	5.3 (4)	C14—N3—N1—C8	179.4 (2)
C3—C4—C5—C6	−0.5 (4)	C7—C8—N1—C15	133.4 (3)
C7—C4—C5—C6	175.1 (3)	C9—C8—N1—C15	−50.9 (4)
C2—C1—C6—C5	0.4 (5)	C7—C8—N1—N3	−44.5 (3)
Cl1—C1—C6—C5	−179.5 (2)	C9—C8—N1—N3	131.1 (2)
C4—C5—C6—C1	0.0 (4)	N1—C15—N2—C14	1.5 (3)
C5—C4—C7—C8	60.7 (4)	N1—C15—N2—Co1	−168.98 (17)
C3—C4—C7—C8	−123.9 (3)	N2ⁱ—Co1—N2—C15	46 (100)
C4—C7—C8—N1	−179.2 (2)	N4ⁱ—Co1—N2—C15	−143.4 (2)
C4—C7—C8—C9	5.7 (4)	N4—Co1—N2—C15	36.6 (2)
C7—C8—C9—O1	−134.4 (3)	Cl5ⁱ—Co1—N2—C15	127.4 (2)
N1—C8—C9—O1	50.5 (3)	Cl5—Co1—N2—C15	−52.6 (2)
C7—C8—C9—C10	102.1 (3)	N2ⁱ—Co1—N2—C14	−122 (100)
N1—C8—C9—C10	−73.1 (3)	N4ⁱ—Co1—N2—C14	48.5 (2)
O1—C9—C10—C11	−54.3 (3)	N4—Co1—N2—C14	−131.5 (2)
C8—C9—C10—C11	71.1 (3)	Cl5ⁱ—Co1—N2—C14	−40.7 (2)
O1—C9—C10—C12	65.2 (3)	Cl5—Co1—N2—C14	139.3 (2)
C8—C9—C10—C12	−169.4 (3)	N1—N3—C14—N2	−0.1 (3)
O1—C9—C10—C13	−177.1 (3)	C15—N2—C14—N3	−0.8 (3)
C8—C9—C10—C13	−51.7 (3)	Co1—N2—C14—N3	169.63 (19)
C24—C18—C19—O2	−131.9 (3)	N6—C17—N4—C16	−0.7 (3)
N6—C18—C19—O2	50.7 (3)	N6—C17—N4—Co1	164.63 (16)
C24—C18—C19—C20	103.3 (3)	N5—C16—N4—C17	0.4 (4)
N6—C18—C19—C20	−74.0 (3)	N5—C16—N4—Co1	−164.3 (2)
O2—C19—C20—C21	−55.1 (3)	N2—Co1—N4—C17	−66.5 (2)
C18—C19—C20—C21	71.2 (3)	N2ⁱ—Co1—N4—C17	113.5 (2)
O2—C19—C20—C22	64.4 (3)	N4ⁱ—Co1—N4—C17	151 (100)
C18—C19—C20—C22	−169.2 (2)	Cl5ⁱ—Co1—N4—C17	−154.7 (2)
O2—C19—C20—C23	−177.7 (2)	Cl5—Co1—N4—C17	25.3 (2)
C18—C19—C20—C23	−51.4 (3)	N2—Co1—N4—C16	94.9 (2)
N6—C18—C24—C25	−176.3 (2)	N2ⁱ—Co1—N4—C16	−85.1 (2)
C19—C18—C24—C25	6.3 (4)	N4ⁱ—Co1—N4—C16	−48 (100)
C18—C24—C25—C26	−119.7 (3)	Cl5ⁱ—Co1—N4—C16	6.7 (2)
C18—C24—C25—C30	61.0 (4)	Cl5—Co1—N4—C16	−173.3 (2)
C30—C25—C26—C27	−4.0 (4)	N4—C16—N5—N6	0.1 (4)
C24—C25—C26—C27	176.7 (2)	N4—C17—N6—N5	0.8 (3)
C30—C25—C26—Cl4	177.9 (2)	N4—C17—N6—C18	−173.2 (2)
C24—C25—C26—Cl4	−1.5 (4)	C16—N5—N6—C17	−0.5 (3)
C25—C26—C27—C28	0.2 (4)	C16—N5—N6—C18	174.0 (2)
Cl4—C26—C27—C28	178.4 (2)	C24—C18—N6—C17	144.7 (3)
C26—C27—C28—C29	3.7 (4)	C19—C18—N6—C17	−37.7 (4)
C26—C27—C28—Cl3	−175.5 (2)	C24—C18—N6—N5	−28.7 (4)
C27—C28—C29—C30	−3.6 (4)	C19—C18—N6—N5	148.9 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl5ⁱⁱ	0.82	2.35	3.136 (2)	161
O2—H2A···Cl5ⁱⁱ	0.82	2.32	3.128 (2)	169

Symmetry code: (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[CoCl₂(C₁₅H₁₇Cl₂N₃O)₄]
M_r	1434.69
Crystal system, space group	Triclinic, 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)
V (Å³)	1729.0 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.25 × 0.21 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.847, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	12895, 6356, 4764
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.098, 1.02
No. of reflections	6356
No. of parameters	402
No. of restraints	70
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.53

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl5ⁱ	0.82	2.35	3.136 (2)	161.2
O2—H2A···Cl5ⁱ	0.82	2.32	3.128 (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

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