Dichloridotetra­kis­(diniconazole)nickel(II)

Xiong, Z.-Q.; Song, X.-Y.; Nie, X.-L.

doi:10.1107/S160053681103128X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1213

doi:10.1107/S160053681103128X

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Dichloridotetrakis(diniconazole)nickel(II)

Zhi-Qiang Xiong,^a Xiu-Ying Song ^b and Xu-Liang Nie ^b ^*

^aInstrumental Analysis Center, Nanchang Hangkong University, Nanchang 330063, People's Republic of China, and ^bCollege 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 6 August 2011)

In the title compound, [NiCl₂(C₁₅H₁₇Cl₂N₃O)₄], the Ni atom lies on an inversion center and has an axially extended trans-NiCl₂N₄ octahedral geometry arising from its coordination by 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 and two chloride ions. In the crystal, O—H⋯Cl hydrogen bonds link the molecules into [100] chains.

Related literature

For background to the use of diniconazole as a fungicide, see: Sumitomo Chemical (1984 ); Huang et al. (2003 ); Zhou et al. (2008 ). For further synthetic details, see: Fu (2002 ); Xia et al. (2001 ). For the isotypic zinc complex, see: Gao et al. (2001 ). For our previous work based on diniconazole, see: Xiong et al. (2010 ).

Experimental

Crystal data

[NiCl₂(C₁₅H₁₇Cl₂N₃O)₄]
M_r = 1434.47
Triclinic, $[P \overline 1]$
a = 8.7598 (6) Å
b = 13.7800 (9) Å
c = 15.1344 (10) Å
α = 90.672 (1)°
β = 98.521 (1)°
γ = 106.743 (1)°
V = 1727.3 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 296 K
0.25 × 0.22 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.840, T_max = 0.863
13440 measured reflections
6383 independent reflections
4766 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.02
6383 reflections
402 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.091 (2)
Ni1—N4	2.106 (2)
Ni1—Cl1	2.4860 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl1ⁱ	0.82	2.36	3.1460 (19)	160
O2—H2A⋯Cl1ⁱ	0.82	2.32	3.123 (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: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681103128X/hb6336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103128X/hb6336Isup2.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; Zhou et al., 2008). 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 nickel(II) complex, (I), incorporating diniconazole.

The asymmetric unit of the title compound, [Ni(C₁₅H₁₇Cl₂N₃O) ₄Cl₂], consists of one nickel(II) ion, two diniconazole ligands and one coordinated chloride ion. The Ni 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 Ni—N distance are 2.123 (3) and 2.147 (3) Å and Ni—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 Zn²⁺ 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); Zhou et al. (2008). For further synthetic details, see: Fu et al. (2002); Xia et al. (2001). For the isotypic zinc complex, see: Gao et al. (2001). For our previous work based on diniconazole, see: Xiong et al. (2010).

Experimental top

NiCl₂.6H₂O (0.024 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 NiCl₂ solution was added to the diniconazole solution slowly under stirring. The mixture were filtered after stirring for 1 h. Green blocks of (I) were obtained by slow concentration of an ethanol solution. Anal. Calcd. For C₆₀H₆₈Cl₁₀NiN₁₂O₄ (%) (Mr = 1434.48): C, 50.24; H, 4.78; N, 11.72. Found (%): C, 55.21; H, 4.80; N, 11.70.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 displacement ellipsoids at the 40% probability level.
	Fig. 2. The crystal packing of (I), showing a hydrogen-bonded chain; 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]nickel(II) top

Crystal data top

[NiCl₂(C₁₅H₁₇Cl₂N₃O)₄]	Z = 1
M_r = 1434.47	F(000) = 742
Triclinic, P1	D_x = 1.379 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7598 (6) Å	Cell parameters from 3863 reflections
b = 13.7800 (9) Å	θ = 2.5–26.1°
c = 15.1344 (10) Å	µ = 0.72 mm⁻¹
α = 90.672 (1)°	T = 296 K
β = 98.521 (1)°	Block, green
γ = 106.743 (1)°	0.25 × 0.22 × 0.21 mm
V = 1727.3 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	6383 independent reflections
Radiation source: fine-focus sealed tube	4766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
T_min = 0.840, T_max = 0.863	k = −16→16
13440 measured reflections	l = −18→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0497P)² + 0.4285P] where P = (F_o² + 2F_c²)/3
6383 reflections	(Δ/σ)_max = 0.001
402 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[NiCl₂(C₁₅H₁₇Cl₂N₃O)₄]	γ = 106.743 (1)°
M_r = 1434.47	V = 1727.3 (2) Å³
Triclinic, P1	Z = 1
a = 8.7598 (6) Å	Mo Kα radiation
b = 13.7800 (9) Å	µ = 0.72 mm⁻¹
c = 15.1344 (10) Å	T = 296 K
α = 90.672 (1)°	0.25 × 0.22 × 0.21 mm
β = 98.521 (1)°

Data collection top

Bruker APEXII CCD diffractometer	6383 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	4766 reflections with I > 2σ(I)
T_min = 0.840, T_max = 0.863	R_int = 0.025
13440 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	Δρ_max = 0.35 e Å⁻³
6383 reflections	Δρ_min = −0.42 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
Ni1	0.5000	0.0000	0.5000	0.02802 (13)
Cl1	0.73567 (8)	−0.02454 (5)	0.60068 (4)	0.04154 (18)
Cl5	0.58239 (9)	−0.34451 (7)	0.02533 (5)	0.0630 (2)
Cl2	1.11706 (10)	0.52902 (6)	0.24982 (6)	0.0638 (2)
Cl3	1.66829 (9)	0.47117 (7)	0.18141 (6)	0.0634 (2)
Cl4	1.16064 (13)	−0.36651 (8)	−0.03016 (7)	0.0854 (3)
N4	0.6518 (2)	0.13360 (16)	0.45770 (14)	0.0341 (5)
N3	0.6487 (2)	−0.12645 (16)	0.28494 (13)	0.0332 (5)
N1	0.5419 (2)	−0.08273 (16)	0.39414 (13)	0.0347 (5)
N6	0.8613 (2)	0.23450 (15)	0.41014 (13)	0.0316 (5)
C2	0.6135 (3)	0.2041 (2)	0.4058 (2)	0.0512 (8)
H2	0.5084	0.2081	0.3926	0.061*
C12	0.4329 (3)	−0.1519 (2)	0.33470 (19)	0.0498 (8)
H12	0.3248	−0.1765	0.3412	0.060*
C11	0.6754 (3)	−0.0703 (2)	0.36072 (16)	0.0351 (6)
H11	0.7757	−0.0278	0.3866	0.042*
C20	0.7892 (3)	−0.3141 (2)	0.06064 (17)	0.0404 (7)
C16	1.0225 (3)	−0.2331 (2)	0.16512 (18)	0.0419 (7)
H16	1.0712	−0.1945	0.2181	0.050*
N2	0.4896 (3)	−0.1819 (2)	0.26754 (15)	0.0504 (6)
C13	0.7614 (3)	−0.1355 (2)	0.22698 (15)	0.0317 (6)
C14	0.7522 (3)	−0.2281 (2)	0.19829 (16)	0.0374 (6)
H14	0.6722	−0.2810	0.2164	0.045*
C15	0.8564 (3)	−0.25637 (19)	0.14017 (16)	0.0352 (6)
C19	0.8817 (4)	−0.3476 (2)	0.00823 (19)	0.0485 (7)
H19	0.8341	−0.3863	−0.0448	0.058*
C17	1.1169 (4)	−0.2659 (2)	0.1134 (2)	0.0478 (7)
H17	1.2281	−0.2494	0.1311	0.057*
C18	1.0450 (4)	−0.3230 (2)	0.0357 (2)	0.0493 (8)
C1	0.8086 (3)	0.15564 (19)	0.45978 (16)	0.0336 (6)
H1	0.8741	0.1211	0.4914	0.040*
C27	1.0189 (3)	0.27541 (18)	0.38578 (16)	0.0298 (5)
C8	1.4775 (3)	0.4233 (2)	0.21011 (17)	0.0405 (7)
C9	1.3818 (3)	0.4858 (2)	0.21392 (17)	0.0421 (7)
H9	1.4153	0.5525	0.1973	0.051*
C5	1.1815 (3)	0.3492 (2)	0.26917 (16)	0.0342 (6)
C7	1.4256 (3)	0.3228 (2)	0.23023 (18)	0.0463 (7)
H7	1.4885	0.2798	0.2243	0.056*
C4	1.0282 (3)	0.31053 (19)	0.30519 (17)	0.0355 (6)
H4	0.9329	0.3110	0.2690	0.043*
C6	1.2785 (3)	0.2874 (2)	0.25922 (18)	0.0426 (7)
H6	1.2432	0.2197	0.2726	0.051*
N5	0.7347 (3)	0.26722 (19)	0.37477 (18)	0.0533 (7)
C10	1.2342 (3)	0.4480 (2)	0.24291 (17)	0.0380 (6)
C28	1.1612 (3)	0.2793 (2)	0.45744 (17)	0.0352 (6)
H28	1.2570	0.2937	0.4280	0.042*
C25	0.8684 (3)	−0.0378 (2)	0.19969 (16)	0.0358 (6)
H25	0.9532	−0.0544	0.1725	0.043*
C29	1.1960 (3)	0.3618 (2)	0.53325 (18)	0.0428 (7)
C26	0.7828 (4)	0.0188 (2)	0.13069 (19)	0.0500 (8)
O2	1.1449 (2)	0.18368 (14)	0.49624 (13)	0.0449 (5)
H2A	1.1757	0.1469	0.4644	0.067*
O1	0.9460 (2)	0.03079 (14)	0.27532 (12)	0.0452 (5)
H1A	1.0243	0.0149	0.3002	0.068*
C30	0.6677 (4)	0.0650 (3)	0.1709 (3)	0.0728 (11)
H30A	0.6340	0.1104	0.1300	0.109*
H30B	0.7220	0.1019	0.2264	0.109*
H30C	0.5750	0.0119	0.1816	0.109*
C31	0.9151 (5)	0.1044 (3)	0.0990 (3)	0.0811 (12)
H31A	0.8668	0.1393	0.0535	0.122*
H31B	0.9895	0.0762	0.0749	0.122*
H31C	0.9716	0.1513	0.1486	0.122*
C32	1.0688 (4)	0.3386 (3)	0.5958 (2)	0.0628 (9)
H32A	1.0568	0.2719	0.6171	0.094*
H32B	0.9674	0.3418	0.5637	0.094*
H32C	1.1027	0.3877	0.6457	0.094*
C33	1.3603 (4)	0.3659 (3)	0.5870 (2)	0.0716 (10)
H33A	1.3912	0.4200	0.6325	0.107*
H33B	1.4397	0.3775	0.5478	0.107*
H33C	1.3532	0.3026	0.6145	0.107*
C34	1.2064 (5)	0.4639 (2)	0.4925 (2)	0.0731 (11)
H34A	1.2360	0.5165	0.5394	0.110*
H34B	1.1034	0.4617	0.4589	0.110*
H34C	1.2863	0.4777	0.4536	0.110*
C35	0.6923 (5)	−0.0543 (3)	0.0510 (2)	0.0822 (12)
H35A	0.6015	−0.1035	0.0687	0.123*
H35B	0.7633	−0.0882	0.0307	0.123*
H35C	0.6552	−0.0171	0.0035	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0224 (2)	0.0333 (3)	0.0295 (2)	0.00732 (19)	0.00932 (17)	0.00260 (19)
Cl1	0.0324 (3)	0.0500 (4)	0.0446 (4)	0.0167 (3)	0.0042 (3)	0.0057 (3)
Cl5	0.0451 (4)	0.0772 (6)	0.0583 (5)	0.0079 (4)	0.0038 (4)	−0.0208 (4)
Cl2	0.0602 (5)	0.0569 (5)	0.0886 (6)	0.0290 (4)	0.0312 (4)	0.0276 (4)
Cl3	0.0354 (4)	0.0843 (6)	0.0651 (5)	0.0013 (4)	0.0242 (4)	−0.0009 (4)
Cl4	0.0851 (7)	0.0949 (8)	0.0974 (7)	0.0448 (6)	0.0457 (6)	−0.0131 (6)
N4	0.0270 (11)	0.0379 (13)	0.0384 (12)	0.0075 (10)	0.0125 (9)	0.0064 (10)
N3	0.0280 (11)	0.0401 (13)	0.0317 (11)	0.0084 (10)	0.0082 (9)	−0.0035 (9)
N1	0.0302 (12)	0.0422 (14)	0.0333 (11)	0.0115 (10)	0.0088 (9)	0.0007 (10)
N6	0.0273 (11)	0.0302 (12)	0.0371 (11)	0.0058 (9)	0.0098 (9)	0.0066 (9)
C2	0.0283 (15)	0.055 (2)	0.075 (2)	0.0145 (14)	0.0176 (14)	0.0283 (16)
C12	0.0275 (15)	0.066 (2)	0.0526 (18)	0.0065 (14)	0.0116 (13)	−0.0127 (15)
C11	0.0291 (14)	0.0413 (16)	0.0339 (14)	0.0077 (12)	0.0069 (11)	−0.0045 (11)
C20	0.0421 (16)	0.0396 (17)	0.0404 (15)	0.0102 (13)	0.0129 (12)	−0.0014 (12)
C16	0.0440 (16)	0.0460 (17)	0.0378 (15)	0.0177 (14)	0.0044 (12)	−0.0013 (12)
N2	0.0315 (13)	0.0666 (18)	0.0470 (14)	0.0047 (12)	0.0079 (11)	−0.0173 (12)
C13	0.0296 (13)	0.0413 (16)	0.0248 (12)	0.0118 (12)	0.0038 (10)	−0.0022 (11)
C14	0.0404 (15)	0.0387 (16)	0.0324 (14)	0.0074 (12)	0.0123 (11)	−0.0006 (12)
C15	0.0451 (16)	0.0315 (15)	0.0326 (13)	0.0129 (12)	0.0142 (12)	0.0010 (11)
C19	0.061 (2)	0.0440 (18)	0.0421 (16)	0.0139 (15)	0.0161 (14)	−0.0082 (13)
C17	0.0461 (17)	0.0509 (19)	0.0548 (18)	0.0239 (15)	0.0148 (14)	0.0080 (15)
C18	0.059 (2)	0.0460 (19)	0.0553 (19)	0.0262 (16)	0.0273 (16)	0.0052 (15)
C1	0.0273 (13)	0.0353 (15)	0.0366 (14)	0.0048 (11)	0.0084 (11)	0.0070 (11)
C27	0.0269 (13)	0.0253 (14)	0.0364 (13)	0.0043 (10)	0.0099 (10)	0.0022 (10)
C8	0.0294 (14)	0.0551 (19)	0.0337 (14)	0.0043 (13)	0.0105 (11)	0.0009 (13)
C9	0.0400 (16)	0.0408 (17)	0.0393 (15)	−0.0006 (13)	0.0113 (12)	0.0054 (12)
C5	0.0304 (14)	0.0399 (16)	0.0308 (13)	0.0060 (12)	0.0089 (11)	0.0051 (11)
C7	0.0430 (17)	0.058 (2)	0.0441 (16)	0.0196 (15)	0.0153 (13)	0.0031 (14)
C4	0.0272 (13)	0.0376 (16)	0.0386 (14)	0.0034 (11)	0.0076 (11)	0.0067 (12)
C6	0.0459 (17)	0.0371 (16)	0.0450 (16)	0.0088 (13)	0.0146 (13)	0.0082 (12)
N5	0.0329 (13)	0.0535 (16)	0.0797 (18)	0.0164 (12)	0.0186 (12)	0.0329 (14)
C10	0.0364 (15)	0.0428 (17)	0.0353 (14)	0.0111 (12)	0.0085 (11)	0.0072 (12)
C28	0.0295 (13)	0.0389 (16)	0.0396 (14)	0.0098 (12)	0.0128 (11)	0.0078 (12)
C25	0.0342 (14)	0.0384 (16)	0.0368 (14)	0.0118 (12)	0.0097 (11)	−0.0013 (11)
C29	0.0407 (16)	0.0423 (17)	0.0405 (15)	0.0065 (13)	0.0030 (12)	−0.0013 (13)
C26	0.062 (2)	0.0432 (18)	0.0439 (16)	0.0164 (15)	0.0028 (14)	0.0049 (13)
O2	0.0480 (12)	0.0463 (12)	0.0510 (12)	0.0247 (10)	0.0186 (9)	0.0152 (9)
O1	0.0369 (11)	0.0462 (12)	0.0479 (11)	0.0091 (9)	−0.0006 (9)	−0.0080 (9)
C30	0.077 (3)	0.068 (3)	0.082 (3)	0.041 (2)	0.002 (2)	0.014 (2)
C31	0.102 (3)	0.064 (2)	0.078 (3)	0.017 (2)	0.026 (2)	0.028 (2)
C32	0.065 (2)	0.074 (2)	0.0489 (18)	0.0181 (18)	0.0136 (16)	−0.0163 (16)
C33	0.049 (2)	0.095 (3)	0.056 (2)	0.0064 (19)	−0.0071 (16)	−0.0044 (19)
C34	0.095 (3)	0.040 (2)	0.072 (2)	0.0069 (18)	0.002 (2)	−0.0093 (17)
C35	0.116 (3)	0.071 (3)	0.050 (2)	0.029 (2)	−0.020 (2)	0.0037 (18)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	2.091 (2)	C8—C7	1.380 (4)
Ni1—N1	2.091 (2)	C9—C10	1.386 (4)
Ni1—N4	2.106 (2)	C9—H9	0.9300
Ni1—N4ⁱ	2.106 (2)	C5—C6	1.386 (4)
Ni1—Cl1ⁱ	2.4860 (6)	C5—C10	1.389 (4)
Ni1—Cl1	2.4860 (6)	C5—C4	1.481 (3)
Cl5—C20	1.736 (3)	C7—C6	1.378 (4)
Cl2—C10	1.732 (3)	C7—H7	0.9300
Cl3—C8	1.733 (3)	C4—H4	0.9300
Cl4—C18	1.737 (3)	C6—H6	0.9300
N4—C1	1.314 (3)	C28—O2	1.426 (3)
N4—C2	1.343 (3)	C28—C29	1.539 (4)
N3—C11	1.328 (3)	C28—H28	0.9800
N3—N2	1.367 (3)	C25—O1	1.428 (3)
N3—C13	1.444 (3)	C25—C26	1.545 (4)
N1—C11	1.310 (3)	C25—H25	0.9800
N1—C12	1.353 (3)	C29—C34	1.527 (4)
N6—C1	1.338 (3)	C29—C33	1.531 (4)
N6—N5	1.355 (3)	C29—C32	1.534 (4)
N6—C27	1.438 (3)	C26—C35	1.525 (4)
C2—N5	1.315 (3)	C26—C30	1.528 (5)
C2—H2	0.9300	C26—C31	1.535 (4)
C12—N2	1.307 (3)	O2—H2A	0.8200
C12—H12	0.9300	O1—H1A	0.8200
C11—H11	0.9300	C30—H30A	0.9600
C20—C19	1.377 (4)	C30—H30B	0.9600
C20—C15	1.387 (4)	C30—H30C	0.9600
C16—C17	1.378 (4)	C31—H31A	0.9600
C16—C15	1.389 (4)	C31—H31B	0.9600
C16—H16	0.9300	C31—H31C	0.9600
C13—C14	1.319 (4)	C32—H32A	0.9600
C13—C25	1.504 (4)	C32—H32B	0.9600
C14—C15	1.481 (3)	C32—H32C	0.9600
C14—H14	0.9300	C33—H33A	0.9600
C19—C18	1.370 (4)	C33—H33B	0.9600
C19—H19	0.9300	C33—H33C	0.9600
C17—C18	1.368 (4)	C34—H34A	0.9600
C17—H17	0.9300	C34—H34B	0.9600
C1—H1	0.9300	C34—H34C	0.9600
C27—C4	1.323 (3)	C35—H35A	0.9600
C27—C28	1.514 (3)	C35—H35B	0.9600
C8—C9	1.371 (4)	C35—H35C	0.9600

N1ⁱ—Ni1—N1	180.0	C6—C7—C8	118.7 (3)
N1ⁱ—Ni1—N4	90.43 (8)	C6—C7—H7	120.7
N1—Ni1—N4	89.57 (8)	C8—C7—H7	120.7
N1ⁱ—Ni1—N4ⁱ	89.57 (8)	C27—C4—C5	123.9 (2)
N1—Ni1—N4ⁱ	90.43 (8)	C27—C4—H4	118.1
N4—Ni1—N4ⁱ	180.00 (9)	C5—C4—H4	118.1
N1ⁱ—Ni1—Cl1ⁱ	91.80 (6)	C7—C6—C5	122.4 (3)
N1—Ni1—Cl1ⁱ	88.20 (6)	C7—C6—H6	118.8
N4—Ni1—Cl1ⁱ	90.45 (6)	C5—C6—H6	118.8
N4ⁱ—Ni1—Cl1ⁱ	89.55 (6)	C2—N5—N6	102.3 (2)
N1ⁱ—Ni1—Cl1	88.20 (6)	C9—C10—C5	122.0 (3)
N1—Ni1—Cl1	91.80 (6)	C9—C10—Cl2	118.2 (2)
N4—Ni1—Cl1	89.55 (6)	C5—C10—Cl2	119.8 (2)
N4ⁱ—Ni1—Cl1	90.45 (6)	O2—C28—C27	111.6 (2)
Cl1ⁱ—Ni1—Cl1	180.000 (1)	O2—C28—C29	108.5 (2)
C1—N4—C2	102.5 (2)	C27—C28—C29	115.3 (2)
C1—N4—Ni1	126.49 (17)	O2—C28—H28	107.0
C2—N4—Ni1	129.53 (17)	C27—C28—H28	107.0
C11—N3—N2	109.2 (2)	C29—C28—H28	107.0
C11—N3—C13	129.2 (2)	O1—C25—C13	111.5 (2)
N2—N3—C13	121.6 (2)	O1—C25—C26	108.0 (2)
C11—N1—C12	102.3 (2)	C13—C25—C26	114.9 (2)
C11—N1—Ni1	128.67 (17)	O1—C25—H25	107.4
C12—N1—Ni1	128.40 (17)	C13—C25—H25	107.4
C1—N6—N5	109.0 (2)	C26—C25—H25	107.4
C1—N6—C27	128.9 (2)	C34—C29—C33	109.3 (3)
N5—N6—C27	121.71 (19)	C34—C29—C32	110.2 (3)
N5—C2—N4	115.4 (2)	C33—C29—C32	109.0 (2)
N5—C2—H2	122.3	C34—C29—C28	109.1 (2)
N4—C2—H2	122.3	C33—C29—C28	106.4 (2)
N2—C12—N1	115.6 (2)	C32—C29—C28	112.7 (2)
N2—C12—H12	122.2	C35—C26—C30	110.5 (3)
N1—C12—H12	122.2	C35—C26—C31	109.0 (3)
N1—C11—N3	111.1 (2)	C30—C26—C31	108.9 (3)
N1—C11—H11	124.5	C35—C26—C25	109.1 (2)
N3—C11—H11	124.5	C30—C26—C25	112.3 (2)
C19—C20—C15	122.1 (3)	C31—C26—C25	107.0 (3)
C19—C20—Cl5	118.7 (2)	C28—O2—H2A	109.5
C15—C20—Cl5	119.2 (2)	C25—O1—H1A	109.5
C17—C16—C15	121.6 (3)	C26—C30—H30A	109.5
C17—C16—H16	119.2	C26—C30—H30B	109.5
C15—C16—H16	119.2	H30A—C30—H30B	109.5
C12—N2—N3	101.9 (2)	C26—C30—H30C	109.5
C14—C13—N3	116.9 (2)	H30A—C30—H30C	109.5
C14—C13—C25	126.6 (2)	H30B—C30—H30C	109.5
N3—C13—C25	116.4 (2)	C26—C31—H31A	109.5
C13—C14—C15	126.6 (2)	C26—C31—H31B	109.5
C13—C14—H14	116.7	H31A—C31—H31B	109.5
C15—C14—H14	116.7	C26—C31—H31C	109.5
C20—C15—C16	117.1 (2)	H31A—C31—H31C	109.5
C20—C15—C14	120.6 (2)	H31B—C31—H31C	109.5
C16—C15—C14	122.1 (2)	C29—C32—H32A	109.5
C18—C19—C20	118.7 (3)	C29—C32—H32B	109.5
C18—C19—H19	120.6	H32A—C32—H32B	109.5
C20—C19—H19	120.6	C29—C32—H32C	109.5
C18—C17—C16	119.1 (3)	H32A—C32—H32C	109.5
C18—C17—H17	120.4	H32B—C32—H32C	109.5
C16—C17—H17	120.4	C29—C33—H33A	109.5
C17—C18—C19	121.4 (3)	C29—C33—H33B	109.5
C17—C18—Cl4	120.1 (2)	H33A—C33—H33B	109.5
C19—C18—Cl4	118.5 (2)	C29—C33—H33C	109.5
N4—C1—N6	110.7 (2)	H33A—C33—H33C	109.5
N4—C1—H1	124.6	H33B—C33—H33C	109.5
N6—C1—H1	124.6	C29—C34—H34A	109.5
C4—C27—N6	118.0 (2)	C29—C34—H34B	109.5
C4—C27—C28	125.5 (2)	H34A—C34—H34B	109.5
N6—C27—C28	116.37 (19)	C29—C34—H34C	109.5
C9—C8—C7	121.1 (3)	H34A—C34—H34C	109.5
C9—C8—Cl3	119.7 (2)	H34B—C34—H34C	109.5
C7—C8—Cl3	119.2 (2)	C26—C35—H35A	109.5
C8—C9—C10	118.9 (3)	C26—C35—H35B	109.5
C8—C9—H9	120.6	H35A—C35—H35B	109.5
C10—C9—H9	120.6	C26—C35—H35C	109.5
C6—C5—C10	116.8 (2)	H35A—C35—H35C	109.5
C6—C5—C4	121.2 (2)	H35B—C35—H35C	109.5
C10—C5—C4	122.0 (2)

N1ⁱ—Ni1—N4—C1	112.5 (2)	C20—C19—C18—C17	−0.3 (5)
N1—Ni1—N4—C1	−67.5 (2)	C20—C19—C18—Cl4	179.4 (2)
N4ⁱ—Ni1—N4—C1	−17 (64)	C2—N4—C1—N6	−1.0 (3)
Cl1ⁱ—Ni1—N4—C1	−155.7 (2)	Ni1—N4—C1—N6	166.02 (16)
Cl1—Ni1—N4—C1	24.3 (2)	N5—N6—C1—N4	1.0 (3)
N1ⁱ—Ni1—N4—C2	−84.0 (3)	C27—N6—C1—N4	−172.0 (2)
N1—Ni1—N4—C2	96.0 (3)	C1—N6—C27—C4	143.7 (3)
N4ⁱ—Ni1—N4—C2	146 (65)	N5—N6—C27—C4	−28.5 (4)
Cl1ⁱ—Ni1—N4—C2	7.8 (2)	C1—N6—C27—C28	−39.4 (3)
Cl1—Ni1—N4—C2	−172.2 (2)	N5—N6—C27—C28	148.4 (2)
N1ⁱ—Ni1—N1—C11	−88 (100)	C7—C8—C9—C10	3.3 (4)
N4—Ni1—N1—C11	37.1 (2)	Cl3—C8—C9—C10	−175.63 (19)
N4ⁱ—Ni1—N1—C11	−142.9 (2)	C9—C8—C7—C6	−3.6 (4)
Cl1ⁱ—Ni1—N1—C11	127.5 (2)	Cl3—C8—C7—C6	175.4 (2)
Cl1—Ni1—N1—C11	−52.5 (2)	N6—C27—C4—C5	−176.3 (2)
N1ⁱ—Ni1—N1—C12	103 (100)	C28—C27—C4—C5	7.1 (4)
N4—Ni1—N1—C12	−131.9 (2)	C6—C5—C4—C27	60.4 (4)
N4ⁱ—Ni1—N1—C12	48.1 (2)	C10—C5—C4—C27	−120.3 (3)
Cl1ⁱ—Ni1—N1—C12	−41.4 (2)	C8—C7—C6—C5	−0.2 (4)
Cl1—Ni1—N1—C12	138.6 (2)	C10—C5—C6—C7	4.1 (4)
C1—N4—C2—N5	0.8 (4)	C4—C5—C6—C7	−176.6 (2)
Ni1—N4—C2—N5	−165.7 (2)	N4—C2—N5—N6	−0.2 (4)
C11—N1—C12—N2	−0.5 (3)	C1—N6—N5—C2	−0.4 (3)
Ni1—N1—C12—N2	170.7 (2)	C27—N6—N5—C2	173.1 (2)
C12—N1—C11—N3	1.3 (3)	C8—C9—C10—C5	0.8 (4)
Ni1—N1—C11—N3	−169.85 (16)	C8—C9—C10—Cl2	178.5 (2)
N2—N3—C11—N1	−1.7 (3)	C6—C5—C10—C9	−4.4 (4)
C13—N3—C11—N1	−179.9 (2)	C4—C5—C10—C9	176.3 (2)
N1—C12—N2—N3	−0.5 (3)	C6—C5—C10—Cl2	178.0 (2)
C11—N3—N2—C12	1.3 (3)	C4—C5—C10—Cl2	−1.3 (3)
C13—N3—N2—C12	179.6 (2)	C4—C27—C28—O2	−132.6 (3)
C11—N3—C13—C14	134.6 (3)	N6—C27—C28—O2	50.7 (3)
N2—N3—C13—C14	−43.4 (3)	C4—C27—C28—C29	103.0 (3)
C11—N3—C13—C25	−50.1 (3)	N6—C27—C28—C29	−73.7 (3)
N2—N3—C13—C25	131.9 (2)	C14—C13—C25—O1	−135.0 (3)
N3—C13—C14—C15	−178.7 (2)	N3—C13—C25—O1	50.2 (3)
C25—C13—C14—C15	6.6 (4)	C14—C13—C25—C26	101.7 (3)
C19—C20—C15—C16	0.2 (4)	N3—C13—C25—C26	−73.1 (3)
Cl5—C20—C15—C16	−179.4 (2)	O2—C28—C29—C34	−177.5 (2)
C19—C20—C15—C14	−175.3 (3)	C27—C28—C29—C34	−51.5 (3)
Cl5—C20—C15—C14	5.1 (4)	O2—C28—C29—C33	64.7 (3)
C17—C16—C15—C20	−0.1 (4)	C27—C28—C29—C33	−169.3 (2)
C17—C16—C15—C14	175.4 (2)	O2—C28—C29—C32	−54.8 (3)
C13—C14—C15—C20	−124.7 (3)	C27—C28—C29—C32	71.2 (3)
C13—C14—C15—C16	60.0 (4)	O1—C25—C26—C35	−177.4 (3)
C15—C20—C19—C18	−0.1 (4)	C13—C25—C26—C35	−52.2 (3)
Cl5—C20—C19—C18	179.5 (2)	O1—C25—C26—C30	−54.5 (3)
C15—C16—C17—C18	−0.3 (4)	C13—C25—C26—C30	70.7 (3)
C16—C17—C18—C19	0.4 (4)	O1—C25—C26—C31	64.9 (3)
C16—C17—C18—Cl4	−179.3 (2)	C13—C25—C26—C31	−169.9 (3)

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—H1A···Cl1ⁱⁱ	0.82	2.36	3.1460 (19)	160
O2—H2A···Cl1ⁱⁱ	0.82	2.32	3.123 (2)	169

Symmetry code: (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[NiCl₂(C₁₅H₁₇Cl₂N₃O)₄]
M_r	1434.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.7598 (6), 13.7800 (9), 15.1344 (10)
α, β, γ (°)	90.672 (1), 98.521 (1), 106.743 (1)
V (Å³)	1727.3 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.25 × 0.22 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.840, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	13440, 6383, 4766
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.02
No. of reflections	6383
No. of parameters	402
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.42

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—N1	2.091 (2)	Ni1—Cl1	2.4860 (6)
Ni1—N4	2.106 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1ⁱ	0.82	2.36	3.1460 (19)	160
O2—H2A···Cl1ⁱ	0.82	2.32	3.123 (2)	169

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangxi Agricultural University, China (2964).

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fu, D. Y. (2002). Chin. J. Pestic. 2, 10–12. Google Scholar
Gao, J. S., Ma, D. S., Ma, Z. G. & Chen, G. R. (2001). Chin. J. Mol. Sci. 17, 1, 17–22. Google Scholar
Huang, X. G., Zhao, A. J., Liu, X. G., Zhou, D. H. & Zeng, B. (2003). Acta Agric. Univ. Jiangxiensis, 25, 277–288. Google Scholar
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sumitomo Chemical. (1984). Jpn Pestic. Soc. 6, 229–236. Google Scholar
Xia, H. Y., Duan, Z. X., Tu, Y. M. & Liu, J. H. (2001). Chin. J. Pestic. 40, 12, 12–14. Google Scholar
Xiong, Z.-Q., Chen, J.-Z., Wen, S.-H. & Nie, X.-L. (2010). Acta Cryst. E66, o3278. CrossRef IUCr Journals Google Scholar
Zhou, Z. Y., Li, C. C., Gao, T. C. & Tang, G. J. (2008). J. Anhui Agric. Sci. 36, 11842–11844. CAS Google Scholar