Bis{2-[3-(dimethyl­ammonio)­propyl­imino­methyl-κN]-6-meth­oxy­phenolato-κO1}bis­(thio­cyanato-κN)nickel(II)

Xue, L.-W.; Zhao, G.-Q.; Han, Y.-J.; Chen, L.-H.; Peng, Q.-L.

doi:10.1107/S1600536810038298

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1352

https://doi.org/10.1107/S1600536810038298

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Bis{2-[3-(dimethylammonio)propyliminomethyl-κN]-6-methoxyphenolato-κO¹}bis(thiocyanato-κN)nickel(II)

Ling-Wei Xue,^a ^* Gan-Qing Zhao,^a Yong-Jun Han,^a Li-Hua Chen ^a and Qin-Long Peng ^a

^aCollege of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan Henan 467000, People's Republic of China
^*Correspondence e-mail: pdsuchemistry@163.com

(Received 24 September 2010; accepted 24 September 2010; online 2 October 2010)

The asymmetric unit of the title complex, [Ni(NCS)₂(C₁₃H₂₀N₂O₂)₂], consists of two half-molecules, both of which are completed by crystallographic inversion symmetry (Ni²⁺ site symmetry = $[\overline{1}]$ in both cases). Both metal ions are six-coordinated in distorted trans-NiO₂N₄ geometries arising from two N,O-bidentate Schiff base ligands and two N-bonded thiocyanate ions. The molecular conformations are reinforced by two intramolecular N—H⋯O hydrogen bonds.

Related literature

For related structures and background references, see: Xue et al. (2010a ,b ).

Experimental

Crystal data

[Ni(NCS)₂(C₁₃H₂₀N₂O₂)₂]
M_r = 647.49
Monoclinic, P 2₁ /c
a = 16.228 (2) Å
b = 15.642 (2) Å
c = 13.3912 (18) Å
β = 113.132 (2)°
V = 3126.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 298 K
0.23 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.838, T_max = 0.857
17748 measured reflections
6772 independent reflections
4916 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.02
6772 reflections
385 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	2.0403 (13)
Ni1—N3	2.0809 (18)
Ni1—N1	2.1102 (16)
Ni2—O3	2.0336 (14)
Ni2—N4	2.0990 (15)
Ni2—N6	2.1577 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.91 (1)	1.78 (1)	2.668 (2)	167 (3)
N5—H5A⋯O3ⁱⁱ	0.90 (1)	1.96 (2)	2.764 (2)	149 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: https://doi.org/10.1107/S1600536810038298/hb5649sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038298/hb5649Isup2.hkl

checkCIF report

Comment top

Recently, we have reported a few Schiff base complexes (Xue et al., 2010a,b). In this paper, a new nickel(II) complex with the Schiff base 2-[(3-dimethylammoniopropylimino)methyl]-6-methoxyphenol, is reported.

The complex is a centrosymmetric mononuclear nickel(II) complex, as shown in Fig. 1. The Ni atom, lying on the inversion center, is six-coordinated in an octahedral geometry, with two phenolate O and two imine N atoms from two Schiff base ligands defining the basal plane, and with two thiocyanate N atoms occupying the axial positions. The two amine N atoms are protonated, and form intramolecular N–H···O hydrogen bonds (Table 1) with the phenolate O atoms. The slight distortion of the octahedral coordination can be observed from the coordinate bond lengths and angles (Table 2).

Related literature top

For related structures and background references, see: Xue et al. (2010a,b).

Experimental top

3-Methoxysalicylaldehyde (152 mg, 1.0 mmol), N,N-dimethylpropane-1,3-diamine (102 mg, 1.0 mmol), ammonium thiocyanate (76 mg, 1.0 mmol), and nickel acetate tetrahydrate (249 mg, 1.0 mmol) were dissolved in methanol (80 ml). The mixture was stirred for two hours at room temperature. The resulting solution was left in air for a few days, yielding green blocks of (I).

Structure description top

For related structures and background references, see: Xue et al. (2010a,b).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 structure of (I) with 30% probability displacement ellipsoids.

Bis{2-[3-(dimethylammonio)propyliminomethyl-κN]-6-methoxyphenolato- κO¹}bis(thiocyanato-κN)nickel(II) top

Crystal data top

[Ni(NCS)₂(C₁₃H₂₀N₂O₂)₂]	F(000) = 1368
M_r = 647.49	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5211 reflections
a = 16.228 (2) Å	θ = 2.6–27.2°
b = 15.642 (2) Å	µ = 0.80 mm⁻¹
c = 13.3912 (18) Å	T = 298 K
β = 113.132 (2)°	Block, green
V = 3126.0 (7) Å³	0.23 × 0.23 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	6772 independent reflections
Radiation source: fine-focus sealed tube	4916 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
T_min = 0.838, T_max = 0.857	k = −19→19
17748 measured reflections	l = −17→7

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0418P)² + 0.616P] where P = (F_o² + 2F_c²)/3
6772 reflections	(Δ/σ)_max = 0.001
385 parameters	Δρ_max = 0.26 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Ni(NCS)₂(C₁₃H₂₀N₂O₂)₂]	V = 3126.0 (7) Å³
M_r = 647.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.228 (2) Å	µ = 0.80 mm⁻¹
b = 15.642 (2) Å	T = 298 K
c = 13.3912 (18) Å	0.23 × 0.23 × 0.20 mm
β = 113.132 (2)°

Data collection top

Bruker SMART CCD diffractometer	6772 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4916 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.857	R_int = 0.026
17748 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.26 e Å⁻³
6772 reflections	Δρ_min = −0.38 e Å⁻³
385 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	0.5000	0.0000	0.03134 (10)
Ni2	0.0000	0.5000	0.0000	0.03281 (10)
S1	0.28158 (5)	0.31526 (5)	−0.26156 (5)	0.0710 (2)
S2	0.18778 (4)	0.75758 (4)	0.05566 (5)	0.05524 (17)
O1	0.48274 (9)	0.43998 (8)	0.12568 (11)	0.0399 (3)
O2	0.54271 (11)	0.39569 (10)	0.33999 (13)	0.0592 (4)
O3	0.01284 (9)	0.51671 (8)	0.15603 (11)	0.0395 (3)
O4	−0.02789 (11)	0.52191 (10)	0.33375 (13)	0.0528 (4)
N1	0.38379 (10)	0.57261 (10)	−0.02589 (13)	0.0341 (4)
N2	0.50658 (12)	0.73003 (11)	−0.11985 (15)	0.0408 (4)
N3	0.41756 (12)	0.41330 (11)	−0.11307 (15)	0.0452 (4)
N4	0.11950 (10)	0.42923 (10)	0.05634 (13)	0.0347 (4)
N5	0.00617 (11)	0.31873 (10)	−0.21919 (14)	0.0398 (4)
N6	0.08080 (12)	0.61079 (11)	0.00524 (15)	0.0443 (4)
C1	0.37093 (12)	0.53225 (12)	0.14375 (15)	0.0328 (4)
C2	0.44253 (13)	0.47353 (12)	0.18471 (16)	0.0337 (4)
C3	0.46936 (14)	0.44942 (13)	0.29512 (17)	0.0408 (5)
C4	0.42342 (15)	0.47622 (14)	0.35629 (17)	0.0441 (5)
H4	0.4417	0.4577	0.4278	0.053*
C5	0.35069 (15)	0.53011 (15)	0.31371 (18)	0.0456 (5)
H5	0.3195	0.5473	0.3556	0.055*
C6	0.32498 (13)	0.55794 (13)	0.20875 (17)	0.0395 (5)
H6	0.2762	0.5946	0.1798	0.047*
C7	0.62574 (17)	0.4410 (2)	0.3822 (2)	0.0724 (8)
H7A	0.6307	0.4765	0.3264	0.109*
H7B	0.6744	0.4009	0.4067	0.109*
H7C	0.6279	0.4760	0.4421	0.109*
C8	0.34179 (13)	0.57118 (12)	0.03718 (16)	0.0357 (4)
H8	0.2863	0.5982	0.0119	0.043*
C9	0.34050 (14)	0.62316 (14)	−0.12656 (17)	0.0428 (5)
H9A	0.2767	0.6115	−0.1568	0.051*
H9B	0.3643	0.6052	−0.1793	0.051*
C10	0.35530 (15)	0.71901 (14)	−0.10719 (19)	0.0491 (6)
H10A	0.3274	0.7480	−0.1764	0.059*
H10B	0.3246	0.7375	−0.0617	0.059*
C11	0.45174 (15)	0.74753 (13)	−0.05485 (18)	0.0472 (5)
H11A	0.4529	0.8085	−0.0412	0.057*
H11B	0.4796	0.7192	0.0149	0.057*
C12	0.60227 (16)	0.75222 (18)	−0.0561 (2)	0.0653 (7)
H12A	0.6366	0.7408	−0.0990	0.098*
H12B	0.6250	0.7184	0.0089	0.098*
H12C	0.6069	0.8117	−0.0373	0.098*
C13	0.47408 (16)	0.77696 (15)	−0.22516 (18)	0.0542 (6)
H13A	0.4762	0.8374	−0.2117	0.081*
H13B	0.4135	0.7602	−0.2683	0.081*
H13C	0.5116	0.7635	−0.2634	0.081*
C14	0.14218 (13)	0.42832 (12)	0.24865 (16)	0.0359 (5)
C15	0.06605 (13)	0.47581 (12)	0.24231 (16)	0.0361 (5)
C16	0.04936 (15)	0.48005 (13)	0.33849 (17)	0.0424 (5)
C17	0.10847 (17)	0.44819 (14)	0.43617 (18)	0.0512 (6)
H17	0.0965	0.4543	0.4983	0.061*
C18	0.18630 (16)	0.40673 (14)	0.44204 (18)	0.0517 (6)
H18	0.2275	0.3867	0.5082	0.062*
C19	0.20132 (14)	0.39593 (13)	0.34964 (17)	0.0453 (5)
H19	0.2521	0.3663	0.3533	0.054*
C20	−0.10592 (18)	0.46990 (19)	0.2910 (2)	0.0693 (8)
H20A	−0.1103	0.4453	0.2234	0.104*
H20B	−0.1580	0.5042	0.2790	0.104*
H20C	−0.1022	0.4251	0.3416	0.104*
C21	0.16576 (13)	0.41259 (12)	0.15670 (17)	0.0376 (5)
H21	0.2213	0.3873	0.1723	0.045*
C22	0.16275 (13)	0.40526 (13)	−0.01820 (17)	0.0407 (5)
H22A	0.2264	0.4171	0.0166	0.049*
H22B	0.1383	0.4403	−0.0831	0.049*
C23	0.14924 (14)	0.31075 (14)	−0.05085 (18)	0.0461 (5)
H23A	0.1805	0.2991	−0.0980	0.055*
H23B	0.1772	0.2764	0.0141	0.055*
C24	0.05311 (14)	0.28187 (13)	−0.10793 (17)	0.0448 (5)
H24A	0.0520	0.2200	−0.1135	0.054*
H24B	0.0203	0.2977	−0.0639	0.054*
C25	0.04371 (16)	0.28787 (17)	−0.2978 (2)	0.0575 (6)
H25A	0.0398	0.2267	−0.3023	0.086*
H25B	0.1053	0.3049	−0.2736	0.086*
H25C	0.0102	0.3121	−0.3680	0.086*
C26	−0.09173 (14)	0.30137 (17)	−0.26210 (19)	0.0568 (6)
H26A	−0.1017	0.2408	−0.2647	0.085*
H26B	−0.1199	0.3248	−0.3339	0.085*
H26C	−0.1168	0.3274	−0.2154	0.085*
C27	0.36096 (14)	0.37389 (13)	−0.17575 (16)	0.0374 (5)
C28	0.12526 (14)	0.67114 (13)	0.02399 (16)	0.0378 (5)
H2	0.5041 (18)	0.6730 (7)	−0.132 (2)	0.080*
H5A	0.0166 (17)	0.3749 (7)	−0.207 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0356 (2)	0.02943 (18)	0.03020 (19)	−0.00061 (14)	0.01426 (15)	−0.00052 (14)
Ni2	0.03240 (19)	0.03016 (18)	0.02986 (19)	0.00455 (14)	0.00575 (15)	−0.00108 (14)
S1	0.0568 (4)	0.1032 (6)	0.0513 (4)	−0.0330 (4)	0.0194 (3)	−0.0272 (4)
S2	0.0585 (4)	0.0471 (3)	0.0575 (4)	−0.0116 (3)	0.0200 (3)	0.0014 (3)
O1	0.0518 (9)	0.0349 (7)	0.0406 (8)	0.0074 (6)	0.0264 (7)	0.0048 (6)
O2	0.0665 (11)	0.0570 (10)	0.0538 (10)	0.0182 (9)	0.0232 (9)	0.0186 (8)
O3	0.0434 (8)	0.0371 (7)	0.0321 (7)	0.0099 (6)	0.0084 (6)	−0.0007 (6)
O4	0.0635 (11)	0.0478 (9)	0.0506 (10)	0.0036 (8)	0.0261 (8)	−0.0062 (7)
N1	0.0351 (9)	0.0340 (8)	0.0331 (9)	−0.0007 (7)	0.0133 (7)	0.0008 (7)
N2	0.0445 (10)	0.0334 (9)	0.0467 (10)	0.0033 (8)	0.0204 (9)	0.0088 (8)
N3	0.0477 (11)	0.0399 (10)	0.0444 (10)	−0.0053 (8)	0.0141 (9)	−0.0058 (8)
N4	0.0327 (9)	0.0303 (8)	0.0365 (9)	0.0017 (7)	0.0087 (7)	−0.0034 (7)
N5	0.0380 (9)	0.0345 (9)	0.0427 (10)	0.0024 (8)	0.0113 (8)	−0.0082 (8)
N6	0.0416 (10)	0.0398 (10)	0.0475 (11)	0.0034 (8)	0.0133 (9)	−0.0019 (8)
C1	0.0340 (10)	0.0334 (9)	0.0331 (10)	−0.0070 (8)	0.0153 (9)	−0.0046 (8)
C2	0.0366 (11)	0.0312 (9)	0.0362 (11)	−0.0070 (8)	0.0174 (9)	−0.0030 (8)
C3	0.0460 (12)	0.0382 (11)	0.0384 (12)	−0.0023 (9)	0.0168 (10)	0.0028 (9)
C4	0.0545 (14)	0.0480 (12)	0.0317 (11)	−0.0076 (11)	0.0189 (10)	0.0008 (9)
C5	0.0523 (14)	0.0513 (12)	0.0427 (13)	−0.0087 (11)	0.0288 (11)	−0.0066 (11)
C6	0.0360 (11)	0.0429 (11)	0.0424 (12)	−0.0048 (9)	0.0184 (10)	−0.0035 (10)
C7	0.0526 (16)	0.108 (2)	0.0479 (15)	0.0185 (16)	0.0110 (13)	−0.0012 (15)
C8	0.0307 (10)	0.0389 (11)	0.0377 (11)	0.0003 (8)	0.0136 (9)	−0.0002 (9)
C9	0.0349 (11)	0.0547 (13)	0.0362 (11)	0.0008 (10)	0.0110 (9)	0.0086 (10)
C10	0.0525 (14)	0.0508 (13)	0.0524 (14)	0.0144 (11)	0.0296 (11)	0.0155 (11)
C11	0.0639 (15)	0.0369 (11)	0.0480 (13)	0.0042 (10)	0.0297 (12)	0.0034 (10)
C12	0.0496 (14)	0.0718 (17)	0.0665 (17)	−0.0102 (13)	0.0141 (13)	0.0197 (14)
C13	0.0613 (15)	0.0538 (14)	0.0496 (14)	0.0080 (12)	0.0240 (12)	0.0166 (11)
C14	0.0361 (11)	0.0297 (10)	0.0343 (11)	−0.0036 (8)	0.0056 (9)	0.0014 (8)
C15	0.0415 (11)	0.0263 (9)	0.0331 (11)	−0.0025 (8)	0.0068 (9)	−0.0021 (8)
C16	0.0512 (13)	0.0325 (10)	0.0416 (12)	−0.0030 (9)	0.0162 (11)	−0.0034 (9)
C17	0.0718 (16)	0.0454 (13)	0.0335 (12)	−0.0090 (12)	0.0176 (12)	−0.0002 (10)
C18	0.0560 (14)	0.0461 (13)	0.0386 (13)	−0.0057 (11)	0.0028 (11)	0.0095 (10)
C19	0.0406 (12)	0.0386 (11)	0.0443 (13)	−0.0019 (9)	0.0035 (10)	0.0066 (10)
C20	0.0624 (17)	0.0702 (17)	0.086 (2)	−0.0055 (14)	0.0402 (16)	−0.0064 (16)
C21	0.0303 (10)	0.0284 (9)	0.0460 (12)	0.0010 (8)	0.0064 (9)	0.0015 (9)
C22	0.0343 (11)	0.0443 (12)	0.0393 (11)	0.0029 (9)	0.0098 (9)	−0.0033 (9)
C23	0.0415 (12)	0.0449 (12)	0.0443 (12)	0.0087 (10)	0.0086 (10)	−0.0061 (10)
C24	0.0496 (13)	0.0352 (11)	0.0458 (12)	0.0050 (10)	0.0145 (10)	−0.0024 (9)
C25	0.0553 (15)	0.0642 (16)	0.0575 (15)	0.0057 (12)	0.0269 (12)	−0.0116 (13)
C26	0.0411 (12)	0.0712 (16)	0.0525 (14)	−0.0069 (12)	0.0123 (11)	−0.0120 (13)
C27	0.0397 (11)	0.0398 (11)	0.0367 (11)	0.0031 (9)	0.0194 (10)	0.0008 (9)
C28	0.0386 (11)	0.0380 (11)	0.0357 (11)	0.0089 (9)	0.0134 (9)	0.0035 (9)

Geometric parameters (Å, º) top

Ni1—O1	2.0403 (13)	C7—H7B	0.9600
Ni1—O1ⁱ	2.0403 (13)	C7—H7C	0.9600
Ni1—N3ⁱ	2.0809 (18)	C8—H8	0.9300
Ni1—N3	2.0809 (18)	C9—C10	1.524 (3)
Ni1—N1	2.1102 (16)	C9—H9A	0.9700
Ni1—N1ⁱ	2.1102 (16)	C9—H9B	0.9700
Ni2—O3ⁱⁱ	2.0336 (14)	C10—C11	1.509 (3)
Ni2—O3	2.0336 (14)	C10—H10A	0.9700
Ni2—N4	2.0990 (15)	C10—H10B	0.9700
Ni2—N4ⁱⁱ	2.0990 (15)	C11—H11A	0.9700
Ni2—N6	2.1577 (19)	C11—H11B	0.9700
Ni2—N6ⁱⁱ	2.1577 (19)	C12—H12A	0.9600
S1—C27	1.630 (2)	C12—H12B	0.9600
S2—C28	1.643 (2)	C12—H12C	0.9600
O1—C2	1.316 (2)	C13—H13A	0.9600
O2—C3	1.386 (3)	C13—H13B	0.9600
O2—C7	1.428 (3)	C13—H13C	0.9600
O3—C15	1.306 (2)	C14—C19	1.410 (3)
O4—C16	1.394 (3)	C14—C15	1.415 (3)
O4—C20	1.422 (3)	C14—C21	1.447 (3)
N1—C8	1.277 (2)	C15—C16	1.418 (3)
N1—C9	1.481 (2)	C16—C17	1.376 (3)
N2—C12	1.489 (3)	C17—C18	1.394 (3)
N2—C13	1.490 (3)	C17—H17	0.9300
N2—C11	1.494 (3)	C18—C19	1.362 (3)
N2—H2	0.906 (10)	C18—H18	0.9300
N3—C27	1.150 (2)	C19—H19	0.9300
N4—C21	1.283 (2)	C20—H20A	0.9600
N4—C22	1.477 (3)	C20—H20B	0.9600
N5—C26	1.487 (3)	C20—H20C	0.9600
N5—C25	1.488 (3)	C21—H21	0.9300
N5—C24	1.497 (3)	C22—C23	1.533 (3)
N5—H5A	0.897 (10)	C22—H22A	0.9700
N6—C28	1.154 (3)	C22—H22B	0.9700
C1—C6	1.409 (3)	C23—C24	1.512 (3)
C1—C2	1.412 (3)	C23—H23A	0.9700
C1—C8	1.450 (3)	C23—H23B	0.9700
C2—C3	1.418 (3)	C24—H24A	0.9700
C3—C4	1.372 (3)	C24—H24B	0.9700
C4—C5	1.378 (3)	C25—H25A	0.9600
C4—H4	0.9300	C25—H25B	0.9600
C5—C6	1.371 (3)	C25—H25C	0.9600
C5—H5	0.9300	C26—H26A	0.9600
C6—H6	0.9300	C26—H26B	0.9600
C7—H7A	0.9600	C26—H26C	0.9600

O1—Ni1—O1ⁱ	180.00 (7)	C10—C9—H9B	109.1
O1—Ni1—N3ⁱ	87.54 (6)	H9A—C9—H9B	107.8
O1ⁱ—Ni1—N3ⁱ	92.46 (6)	C11—C10—C9	115.79 (18)
O1—Ni1—N3	92.46 (6)	C11—C10—H10A	108.3
O1ⁱ—Ni1—N3	87.54 (6)	C9—C10—H10A	108.3
N3ⁱ—Ni1—N3	180.00 (7)	C11—C10—H10B	108.3
O1—Ni1—N1	88.84 (6)	C9—C10—H10B	108.3
O1ⁱ—Ni1—N1	91.16 (6)	H10A—C10—H10B	107.4
N3ⁱ—Ni1—N1	92.66 (6)	N2—C11—C10	114.93 (18)
N3—Ni1—N1	87.34 (6)	N2—C11—H11A	108.5
O1—Ni1—N1ⁱ	91.16 (6)	C10—C11—H11A	108.5
O1ⁱ—Ni1—N1ⁱ	88.84 (6)	N2—C11—H11B	108.5
N3ⁱ—Ni1—N1ⁱ	87.34 (6)	C10—C11—H11B	108.5
N3—Ni1—N1ⁱ	92.66 (6)	H11A—C11—H11B	107.5
N1—Ni1—N1ⁱ	180.00 (7)	N2—C12—H12A	109.5
O3ⁱⁱ—Ni2—O3	180.000 (13)	N2—C12—H12B	109.5
O3ⁱⁱ—Ni2—N4	90.50 (6)	H12A—C12—H12B	109.5
O3—Ni2—N4	89.50 (6)	N2—C12—H12C	109.5
O3ⁱⁱ—Ni2—N4ⁱⁱ	89.50 (6)	H12A—C12—H12C	109.5
O3—Ni2—N4ⁱⁱ	90.50 (6)	H12B—C12—H12C	109.5
N4—Ni2—N4ⁱⁱ	180.0	N2—C13—H13A	109.5
O3ⁱⁱ—Ni2—N6	87.27 (6)	N2—C13—H13B	109.5
O3—Ni2—N6	92.73 (6)	H13A—C13—H13B	109.5
N4—Ni2—N6	87.02 (6)	N2—C13—H13C	109.5
N4ⁱⁱ—Ni2—N6	92.98 (6)	H13A—C13—H13C	109.5
O3ⁱⁱ—Ni2—N6ⁱⁱ	92.73 (6)	H13B—C13—H13C	109.5
O3—Ni2—N6ⁱⁱ	87.27 (6)	C19—C14—C15	119.7 (2)
N4—Ni2—N6ⁱⁱ	92.98 (6)	C19—C14—C21	116.57 (19)
N4ⁱⁱ—Ni2—N6ⁱⁱ	87.02 (6)	C15—C14—C21	123.70 (17)
N6—Ni2—N6ⁱⁱ	180.0	O3—C15—C14	124.64 (19)
C2—O1—Ni1	124.97 (12)	O3—C15—C16	118.99 (19)
C3—O2—C7	112.77 (19)	C14—C15—C16	116.35 (18)
C15—O3—Ni2	127.67 (13)	C17—C16—O4	119.5 (2)
C16—O4—C20	113.10 (18)	C17—C16—C15	122.4 (2)
C8—N1—C9	115.21 (16)	O4—C16—C15	118.04 (19)
C8—N1—Ni1	123.83 (13)	C16—C17—C18	120.0 (2)
C9—N1—Ni1	120.71 (13)	C16—C17—H17	120.0
C12—N2—C13	109.21 (17)	C18—C17—H17	120.0
C12—N2—C11	110.42 (18)	C19—C18—C17	119.2 (2)
C13—N2—C11	112.99 (17)	C19—C18—H18	120.4
C12—N2—H2	107.2 (17)	C17—C18—H18	120.4
C13—N2—H2	109.6 (18)	C18—C19—C14	122.0 (2)
C11—N2—H2	107.2 (17)	C18—C19—H19	119.0
C27—N3—Ni1	168.91 (17)	C14—C19—H19	119.0
C21—N4—C22	114.76 (16)	O4—C20—H20A	109.5
C21—N4—Ni2	124.16 (14)	O4—C20—H20B	109.5
C22—N4—Ni2	120.55 (12)	H20A—C20—H20B	109.5
C26—N5—C25	109.85 (17)	O4—C20—H20C	109.5
C26—N5—C24	111.28 (18)	H20A—C20—H20C	109.5
C25—N5—C24	112.90 (17)	H20B—C20—H20C	109.5
C26—N5—H5A	110.2 (17)	N4—C21—C14	127.99 (18)
C25—N5—H5A	110.1 (18)	N4—C21—H21	116.0
C24—N5—H5A	102.3 (18)	C14—C21—H21	116.0
C28—N6—Ni2	169.71 (18)	N4—C22—C23	112.64 (17)
C6—C1—C2	120.01 (18)	N4—C22—H22A	109.1
C6—C1—C8	116.18 (18)	C23—C22—H22A	109.1
C2—C1—C8	123.79 (18)	N4—C22—H22B	109.1
O1—C2—C1	123.56 (18)	C23—C22—H22B	109.1
O1—C2—C3	119.90 (18)	H22A—C22—H22B	107.8
C1—C2—C3	116.52 (18)	C24—C23—C22	115.85 (17)
C4—C3—O2	120.12 (19)	C24—C23—H23A	108.3
C4—C3—C2	121.65 (19)	C22—C23—H23A	108.3
O2—C3—C2	118.21 (19)	C24—C23—H23B	108.3
C3—C4—C5	121.2 (2)	C22—C23—H23B	108.3
C3—C4—H4	119.4	H23A—C23—H23B	107.4
C5—C4—H4	119.4	N5—C24—C23	114.12 (18)
C6—C5—C4	119.0 (2)	N5—C24—H24A	108.7
C6—C5—H5	120.5	C23—C24—H24A	108.7
C4—C5—H5	120.5	N5—C24—H24B	108.7
C5—C6—C1	121.4 (2)	C23—C24—H24B	108.7
C5—C6—H6	119.3	H24A—C24—H24B	107.6
C1—C6—H6	119.3	N5—C25—H25A	109.5
O2—C7—H7A	109.5	N5—C25—H25B	109.5
O2—C7—H7B	109.5	H25A—C25—H25B	109.5
H7A—C7—H7B	109.5	N5—C25—H25C	109.5
O2—C7—H7C	109.5	H25A—C25—H25C	109.5
H7A—C7—H7C	109.5	H25B—C25—H25C	109.5
H7B—C7—H7C	109.5	N5—C26—H26A	109.5
N1—C8—C1	127.30 (18)	N5—C26—H26B	109.5
N1—C8—H8	116.3	H26A—C26—H26B	109.5
C1—C8—H8	116.3	N5—C26—H26C	109.5
N1—C9—C10	112.56 (17)	H26A—C26—H26C	109.5
N1—C9—H9A	109.1	H26B—C26—H26C	109.5
C10—C9—H9A	109.1	N3—C27—S1	178.0 (2)
N1—C9—H9B	109.1	N6—C28—S2	177.5 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.91 (1)	1.78 (1)	2.668 (2)	167 (3)
N5—H5A···O3ⁱⁱ	0.90 (1)	1.96 (2)	2.764 (2)	149 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Ni(NCS)₂(C₁₃H₂₀N₂O₂)₂]
M_r	647.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.228 (2), 15.642 (2), 13.3912 (18)
β (°)	113.132 (2)
V (Å³)	3126.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.23 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.838, 0.857
No. of measured, independent and observed [I > 2σ(I)] reflections	17748, 6772, 4916
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.02
No. of reflections	6772
No. of parameters	385
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.38

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—O1	2.0403 (13)	Ni2—O3	2.0336 (14)
Ni1—N3	2.0809 (18)	Ni2—N4	2.0990 (15)
Ni1—N1	2.1102 (16)	Ni2—N6	2.1577 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.906 (10)	1.778 (12)	2.668 (2)	167 (3)
N5—H5A···O3ⁱⁱ	0.897 (10)	1.957 (16)	2.764 (2)	149 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Acknowledgements

We thank the Top-Class Foundation and the Applied Chemistry Key Laboratory Foundation of Pingdingshan University.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). 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
Xue, L.-W., Zhao, G.-Q., Han, Y.-J., Chen, L.-H. & Peng, Q.-L. (2010b). Acta Cryst. E66, m1274. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xue, L.-W., Zhao, G.-Q., Han, Y.-J. & Feng, Y.-X. (2010a). Acta Cryst. E66, m1172–m1173. Web of Science CSD CrossRef IUCr Journals Google Scholar

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