Tetra­kis[1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one-κN4]bis­(thio­cyanato-κN)nickel(II)

Guo, J.-H.

doi:10.1107/S1600536810049081

metal-organic compounds

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Volume 66| Part 12| December 2010| Page m1687

https://doi.org/10.1107/S1600536810049081

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Tetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one-κN⁴]bis(thiocyanato-κN)nickel(II)

Jian-Hua Guo ^a ^*

^aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: guojianhua1998@163.com

(Received 9 November 2010; accepted 24 November 2010; online 27 November 2010)

In the centrosymmetric mononuclear title complex, [Ni(NCS)₂(C₁₁H₁₁N₃O)₄], the Ni^II atom, located on an inversion centre, is hexacoordinated in a distorted octahedral geometry comprising four N atoms of four monodentate 1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one ligands and two N atoms from thiocyanate anions.

Related literature

Pseudohalide anions N₃⁻, NCS⁻ and NCO⁻ are versatile ligands in coordination chemistry because of their multiple bridging modes, see: Yue et al. (2008 ). For a related structure, see: Guo & Cai (2007 ).

Experimental

Crystal data

[Ni(NCS)₂(C₁₁H₁₁N₃O)₄]
M_r = 979.78
Triclinic, $[P \overline 1]$
a = 7.8067 (10) Å
b = 11.8539 (15) Å
c = 13.8179 (17) Å
α = 68.907 (2)°
β = 74.765 (2)°
γ = 81.687 (2)°
V = 1149.3 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.57 mm⁻¹
T = 293 K
0.32 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.838, T_max = 0.884
6289 measured reflections
4016 independent reflections
3540 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.080
S = 1.06
4016 reflections
304 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); 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/S1600536810049081/pk2286sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049081/pk2286Isup2.hkl

checkCIF report

Comment top

Pseudohalide anions N₃^-, NCS^- and NCO^- are known as extremely versatile ligands in coordination chemistry because of their multiple bridging modes (Yue et al., 2008). Recently, we have initiated a research program of synthesizing supramolecules based on pseudohalide and flexible ligands that consist of a propanone unit substituted with an imidazole and a phenyl group (Guo et al., 2007). To further explore this series, we synthesized the title compound, a new Ni^II complex based on the mixed ligands thiocyanato and 3-(1H-1,2,4-triazol-1-yl)-1-phenylpropan-1-one (L), which consists of a propanone unit substituted with an triazole and a phenyl group. The crystal structure of the compound consists of a neutral mononuclear [Ni(L)₄(SCN)₂] molecule. As shown in Fig. 1, the Ni^II centre is coordinated by four N atoms from four L ligands, with Ni—N bond lengths in the range 2.103 (1)–2.135 (1) Å, two additional N donor from SCN anion, with a Ni—N bond distance of 2.078 (2) Å. Thus, the coordination polyhedron around the Ni^II cation could be best described as a distorted octahedral geometry. Analysis of the crystal packing indicates that there were no hydrogen bond or πi-πi stacking interactions in the crystal structure. (see Fig. 2).

Related literature top

Pseudohalide anions N₃^-, NCS^- and NCO^- are versatile ligands in coordination chemistry because of their multiple bridging modes, see: Yue et al. (2008). For a related structure, see: Guo & Cai (2007).

Experimental top

Ni(NO₃)₂.6H₂O (29.1 mg, 0.1 mmol), 3-(1H-1,2,4-triazol-1-yl)-1-phenylpropan-1-one (22.3 mg, 0.1 mmol) and NH₄SCN (7.6 mg, 0.1 mmol) were mixed in a CH₃CN—H₂O (20 ml, 1:1 v/v) solution with vigorous stirring for ca 30 min. The resulting solution was filtered and left to stand at room temperature. Green block crystals suitable for X-ray analysis were obtained in 60% yield by slow evaporation of the solvent over a period of 1 week. Analysis, calculated for NiC₄₆H₄₄N₁₄O₄S₂: C 56.39, H 4.53, N 20.01; found: C 56.44, H 4.64, N 20.05.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 title complex with atom labeling, shown with 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing view of compound.

Tetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one- κN⁴]bis(thiocyanato-κN)nickel(II) top

Crystal data top

[Ni(NCS)₂(C₁₁H₁₁N₃O)₄]	Z = 1
M_r = 979.78	F(000) = 510
Triclinic, P1	D_x = 1.416 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8067 (10) Å	Cell parameters from 3376 reflections
b = 11.8539 (15) Å	θ = 2.7–27.7°
c = 13.8179 (17) Å	µ = 0.57 mm⁻¹
α = 68.907 (2)°	T = 293 K
β = 74.765 (2)°	Block, green
γ = 81.687 (2)°	0.32 × 0.28 × 0.22 mm
V = 1149.3 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4016 independent reflections
Radiation source: fine-focus sealed tube	3540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.838, T_max = 0.884	k = −14→12
6289 measured reflections	l = −16→12

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.040P)² + 0.2997P] where P = (F_o² + 2F_c²)/3
4016 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ni(NCS)₂(C₁₁H₁₁N₃O)₄]	γ = 81.687 (2)°
M_r = 979.78	V = 1149.3 (3) Å³
Triclinic, P1	Z = 1
a = 7.8067 (10) Å	Mo Kα radiation
b = 11.8539 (15) Å	µ = 0.57 mm⁻¹
c = 13.8179 (17) Å	T = 293 K
α = 68.907 (2)°	0.32 × 0.28 × 0.22 mm
β = 74.765 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4016 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3540 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.884	R_int = 0.015
6289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	1 restraint
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
4016 reflections	Δρ_min = −0.34 e Å⁻³
304 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.0000	0.0000	1.0000	0.03496 (10)
S1	0.33805 (8)	0.17536 (5)	1.13687 (5)	0.06495 (17)
O1	−0.2740 (2)	0.43272 (14)	0.66743 (14)	0.0764 (5)
O2	0.7081 (2)	0.11988 (13)	0.41955 (11)	0.0655 (4)
N1	−0.13110 (18)	0.17612 (12)	0.96907 (11)	0.0392 (3)
N2	−0.3141 (2)	0.33084 (13)	0.91887 (12)	0.0452 (4)
N3	−0.2531 (2)	0.35006 (14)	0.99458 (13)	0.0532 (4)
N4	0.22222 (18)	0.06368 (13)	0.87523 (10)	0.0396 (3)
N5	0.42461 (19)	0.09149 (13)	0.72860 (11)	0.0413 (3)
N6	0.4816 (2)	0.14708 (15)	0.78321 (12)	0.0524 (4)
N7	0.1164 (2)	0.03338 (14)	1.10545 (12)	0.0463 (4)
C1	−0.1443 (3)	0.25495 (17)	1.02134 (14)	0.0482 (4)
H1	−0.0805	0.2426	1.0728	0.058*
C2	−0.2417 (2)	0.22777 (16)	0.90504 (14)	0.0433 (4)
H2	−0.2650	0.1963	0.8574	0.052*
C3	−0.4513 (3)	0.41348 (18)	0.87177 (18)	0.0575 (5)
H3A	−0.5452	0.4287	0.9282	0.069*
H3B	−0.5027	0.3749	0.8357	0.069*
C4	−0.3814 (3)	0.53338 (17)	0.79313 (15)	0.0517 (5)
H4A	−0.4803	0.5932	0.7850	0.062*
H4B	−0.3006	0.5603	0.8219	0.062*
C5	−0.2859 (3)	0.52697 (17)	0.68498 (17)	0.0512 (5)
C6	−0.2094 (3)	0.63838 (17)	0.59972 (15)	0.0478 (4)
C7	−0.2128 (3)	0.74666 (18)	0.61733 (17)	0.0589 (5)
H7	−0.2664	0.7521	0.6842	0.071*
C8	−0.1372 (3)	0.8465 (2)	0.53641 (19)	0.0696 (6)
H8	−0.1401	0.9186	0.5493	0.084*
C9	−0.0584 (3)	0.8405 (2)	0.43801 (19)	0.0694 (6)
H9	−0.0070	0.9081	0.3840	0.083*
C10	−0.0551 (3)	0.7347 (2)	0.41887 (19)	0.0725 (7)
H10	−0.0023	0.7306	0.3514	0.087*
C11	−0.1297 (3)	0.6340 (2)	0.49890 (17)	0.0618 (6)
H11	−0.1263	0.5624	0.4851	0.074*
C12	0.3558 (3)	0.12746 (18)	0.87042 (14)	0.0501 (5)
H12	0.3584	0.1553	0.9249	0.060*
C13	0.2719 (2)	0.04232 (16)	0.78431 (13)	0.0430 (4)
H13	0.2086	−0.0012	0.7625	0.052*
C14	0.5325 (3)	0.08618 (17)	0.62641 (14)	0.0493 (5)
H14A	0.4685	0.0474	0.5967	0.059*
H14B	0.6421	0.0382	0.6369	0.059*
C15	0.5753 (2)	0.21197 (16)	0.54981 (13)	0.0448 (4)
H15A	0.4652	0.2606	0.5427	0.054*
H15B	0.6432	0.2490	0.5789	0.054*
C16	0.6796 (2)	0.21220 (17)	0.44120 (14)	0.0433 (4)
C17	0.7446 (2)	0.32998 (16)	0.36077 (13)	0.0409 (4)
C18	0.6985 (3)	0.43852 (18)	0.37917 (15)	0.0540 (5)
H18	0.6274	0.4396	0.4445	0.065*
C19	0.7573 (3)	0.54573 (19)	0.30103 (17)	0.0640 (6)
H19	0.7237	0.6188	0.3134	0.077*
C20	0.8645 (3)	0.5447 (2)	0.20578 (16)	0.0605 (6)
H20	0.9041	0.6170	0.1535	0.073*
C21	0.9141 (3)	0.4374 (2)	0.18690 (16)	0.0633 (6)
H21	0.9881	0.4368	0.1222	0.076*
C22	0.8541 (3)	0.33028 (19)	0.26387 (15)	0.0549 (5)
H22	0.8873	0.2577	0.2506	0.066*
C23	0.2074 (2)	0.09092 (16)	1.12141 (13)	0.0401 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03343 (17)	0.03979 (18)	0.02712 (16)	−0.01089 (12)	−0.00462 (12)	−0.00422 (12)
S1	0.0753 (4)	0.0712 (4)	0.0618 (3)	−0.0221 (3)	−0.0177 (3)	−0.0299 (3)
O1	0.0911 (12)	0.0527 (9)	0.0871 (11)	−0.0029 (8)	−0.0070 (9)	−0.0353 (8)
O2	0.0860 (11)	0.0510 (8)	0.0485 (8)	−0.0119 (7)	0.0079 (7)	−0.0171 (7)
N1	0.0398 (8)	0.0403 (8)	0.0326 (7)	−0.0093 (6)	−0.0067 (6)	−0.0048 (6)
N2	0.0433 (8)	0.0441 (8)	0.0441 (8)	−0.0059 (7)	−0.0123 (7)	−0.0070 (7)
N3	0.0634 (10)	0.0478 (9)	0.0490 (9)	−0.0007 (8)	−0.0173 (8)	−0.0148 (7)
N4	0.0383 (8)	0.0434 (8)	0.0313 (7)	−0.0106 (6)	−0.0035 (6)	−0.0059 (6)
N5	0.0421 (8)	0.0440 (8)	0.0316 (7)	−0.0120 (6)	−0.0004 (6)	−0.0074 (6)
N6	0.0522 (9)	0.0625 (10)	0.0407 (8)	−0.0271 (8)	0.0016 (7)	−0.0149 (7)
N7	0.0434 (8)	0.0555 (9)	0.0386 (8)	−0.0095 (7)	−0.0108 (7)	−0.0106 (7)
C1	0.0595 (12)	0.0468 (10)	0.0389 (10)	−0.0058 (9)	−0.0163 (9)	−0.0103 (8)
C2	0.0427 (10)	0.0456 (10)	0.0390 (9)	−0.0107 (8)	−0.0085 (8)	−0.0089 (8)
C3	0.0442 (11)	0.0561 (12)	0.0645 (13)	0.0005 (9)	−0.0162 (10)	−0.0099 (10)
C4	0.0539 (11)	0.0465 (10)	0.0526 (11)	0.0065 (9)	−0.0187 (9)	−0.0131 (9)
C5	0.0485 (11)	0.0462 (11)	0.0617 (12)	0.0077 (8)	−0.0199 (9)	−0.0204 (9)
C6	0.0481 (11)	0.0468 (10)	0.0494 (11)	0.0110 (8)	−0.0187 (9)	−0.0169 (8)
C7	0.0749 (14)	0.0495 (11)	0.0498 (11)	0.0059 (10)	−0.0145 (10)	−0.0172 (9)
C8	0.0873 (17)	0.0482 (12)	0.0687 (15)	0.0031 (11)	−0.0207 (13)	−0.0149 (11)
C9	0.0619 (14)	0.0622 (14)	0.0656 (15)	0.0035 (11)	−0.0142 (11)	−0.0027 (11)
C10	0.0664 (15)	0.0860 (18)	0.0514 (13)	0.0121 (13)	−0.0045 (11)	−0.0196 (12)
C11	0.0651 (13)	0.0624 (13)	0.0596 (13)	0.0122 (11)	−0.0150 (11)	−0.0282 (11)
C12	0.0558 (11)	0.0570 (11)	0.0366 (9)	−0.0258 (9)	0.0021 (8)	−0.0152 (8)
C13	0.0409 (10)	0.0501 (10)	0.0346 (9)	−0.0159 (8)	−0.0054 (7)	−0.0075 (8)
C14	0.0524 (11)	0.0510 (11)	0.0353 (9)	−0.0089 (9)	0.0050 (8)	−0.0120 (8)
C15	0.0436 (10)	0.0480 (10)	0.0337 (9)	−0.0043 (8)	−0.0008 (7)	−0.0080 (8)
C16	0.0409 (10)	0.0480 (10)	0.0361 (9)	−0.0038 (8)	−0.0054 (7)	−0.0106 (8)
C17	0.0383 (9)	0.0477 (10)	0.0323 (9)	−0.0046 (8)	−0.0070 (7)	−0.0082 (7)
C18	0.0627 (12)	0.0512 (11)	0.0382 (10)	−0.0030 (9)	−0.0022 (9)	−0.0098 (8)
C19	0.0799 (16)	0.0478 (11)	0.0563 (13)	−0.0061 (11)	−0.0133 (11)	−0.0088 (10)
C20	0.0604 (13)	0.0596 (13)	0.0482 (12)	−0.0217 (10)	−0.0102 (10)	0.0027 (10)
C21	0.0624 (13)	0.0771 (15)	0.0361 (10)	−0.0192 (11)	0.0063 (9)	−0.0088 (10)
C22	0.0611 (12)	0.0584 (12)	0.0385 (10)	−0.0109 (10)	0.0022 (9)	−0.0152 (9)
C23	0.0417 (9)	0.0467 (10)	0.0299 (8)	−0.0030 (7)	−0.0084 (7)	−0.0101 (7)

Geometric parameters (Å, º) top

Ni1—N7ⁱ	2.0783 (15)	C6—C7	1.385 (3)
Ni1—N7	2.0783 (15)	C6—C11	1.385 (3)
Ni1—N4	2.1028 (13)	C7—C8	1.379 (3)
Ni1—N4ⁱ	2.1028 (13)	C7—H7	0.9300
Ni1—N1	2.1351 (14)	C8—C9	1.360 (3)
Ni1—N1ⁱ	2.1351 (14)	C8—H8	0.9300
S1—C23	1.6282 (19)	C9—C10	1.368 (4)
O1—C5	1.212 (2)	C9—H9	0.9300
O2—C16	1.211 (2)	C10—C11	1.378 (3)
N1—C2	1.327 (2)	C10—H10	0.9300
N1—C1	1.351 (2)	C11—H11	0.9300
N2—C2	1.327 (2)	C12—H12	0.9300
N2—N3	1.355 (2)	C13—H13	0.9300
N2—C3	1.461 (2)	C14—C15	1.509 (2)
N3—C1	1.311 (2)	C14—H14A	0.9700
N4—C13	1.318 (2)	C14—H14B	0.9700
N4—C12	1.349 (2)	C15—C16	1.507 (2)
N5—C13	1.322 (2)	C15—H15A	0.9700
N5—N6	1.349 (2)	C15—H15B	0.9700
N5—C14	1.460 (2)	C16—C17	1.495 (2)
N6—C12	1.309 (2)	C17—C18	1.379 (3)
N7—C23	1.162 (2)	C17—C22	1.385 (2)
C1—H1	0.9300	C18—C19	1.383 (3)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.516 (3)	C19—C20	1.365 (3)
C3—H3A	0.9700	C19—H19	0.9300
C3—H3B	0.9700	C20—C21	1.371 (3)
C4—C5	1.508 (3)	C20—H20	0.9300
C4—H4A	0.9700	C21—C22	1.379 (3)
C4—H4B	0.9700	C21—H21	0.9300
C5—C6	1.492 (3)	C22—H22	0.9300

N7ⁱ—Ni1—N7	180.0	C8—C7—H7	119.8
N7ⁱ—Ni1—N4	89.53 (6)	C6—C7—H7	119.8
N7—Ni1—N4	90.47 (6)	C9—C8—C7	120.7 (2)
N7ⁱ—Ni1—N4ⁱ	90.47 (6)	C9—C8—H8	119.7
N7—Ni1—N4ⁱ	89.53 (6)	C7—C8—H8	119.7
N4—Ni1—N4ⁱ	180.0	C8—C9—C10	119.7 (2)
N7ⁱ—Ni1—N1	90.38 (6)	C8—C9—H9	120.2
N7—Ni1—N1	89.62 (6)	C10—C9—H9	120.2
N4—Ni1—N1	92.47 (5)	C9—C10—C11	120.4 (2)
N4ⁱ—Ni1—N1	87.53 (5)	C9—C10—H10	119.8
N7ⁱ—Ni1—N1ⁱ	89.62 (6)	C11—C10—H10	119.8
N7—Ni1—N1ⁱ	90.38 (6)	C10—C11—C6	120.6 (2)
N4—Ni1—N1ⁱ	87.53 (5)	C10—C11—H11	119.7
N4ⁱ—Ni1—N1ⁱ	92.47 (5)	C6—C11—H11	119.7
N1—Ni1—N1ⁱ	180.0	N6—C12—N4	114.85 (17)
C2—N1—C1	102.31 (15)	N6—C12—H12	122.6
C2—N1—Ni1	128.52 (13)	N4—C12—H12	122.6
C1—N1—Ni1	128.48 (12)	N4—C13—N5	110.34 (16)
C2—N2—N3	110.13 (15)	N4—C13—H13	124.8
C2—N2—C3	129.49 (17)	N5—C13—H13	124.8
N3—N2—C3	120.18 (16)	N5—C14—C15	110.42 (15)
C1—N3—N2	102.04 (15)	N5—C14—H14A	109.6
C13—N4—C12	102.53 (14)	C15—C14—H14A	109.6
C13—N4—Ni1	127.68 (12)	N5—C14—H14B	109.6
C12—N4—Ni1	129.61 (12)	C15—C14—H14B	109.6
C13—N5—N6	109.87 (14)	H14A—C14—H14B	108.1
C13—N5—C14	129.32 (16)	C16—C15—C14	112.64 (15)
N6—N5—C14	120.71 (14)	C16—C15—H15A	109.1
C12—N6—N5	102.40 (14)	C14—C15—H15A	109.1
C23—N7—Ni1	149.53 (14)	C16—C15—H15B	109.1
N3—C1—N1	115.41 (17)	C14—C15—H15B	109.1
N3—C1—H1	122.3	H15A—C15—H15B	107.8
N1—C1—H1	122.3	O2—C16—C17	121.11 (16)
N2—C2—N1	110.11 (17)	O2—C16—C15	120.90 (16)
N2—C2—H2	124.9	C17—C16—C15	117.98 (16)
N1—C2—H2	124.9	C18—C17—C22	118.80 (17)
N2—C3—C4	113.09 (16)	C18—C17—C16	122.40 (16)
N2—C3—H3A	109.0	C22—C17—C16	118.79 (17)
C4—C3—H3A	109.0	C17—C18—C19	120.34 (19)
N2—C3—H3B	109.0	C17—C18—H18	119.8
C4—C3—H3B	109.0	C19—C18—H18	119.8
H3A—C3—H3B	107.8	C20—C19—C18	120.2 (2)
C5—C4—C3	113.39 (17)	C20—C19—H19	119.9
C5—C4—H4A	108.9	C18—C19—H19	119.9
C3—C4—H4A	108.9	C19—C20—C21	120.16 (19)
C5—C4—H4B	108.9	C19—C20—H20	119.9
C3—C4—H4B	108.9	C21—C20—H20	119.9
H4A—C4—H4B	107.7	C20—C21—C22	119.97 (19)
O1—C5—C6	120.63 (19)	C20—C21—H21	120.0
O1—C5—C4	120.17 (19)	C22—C21—H21	120.0
C6—C5—C4	119.19 (17)	C21—C22—C17	120.5 (2)
C7—C6—C11	118.2 (2)	C21—C22—H22	119.8
C7—C6—C5	122.69 (18)	C17—C22—H22	119.8
C11—C6—C5	119.16 (18)	N7—C23—S1	176.90 (16)
C8—C7—C6	120.5 (2)

N7ⁱ—Ni1—N1—C2	0.68 (14)	O1—C5—C6—C7	−177.0 (2)
N7—Ni1—N1—C2	−179.32 (14)	C4—C5—C6—C7	4.0 (3)
N4—Ni1—N1—C2	90.22 (14)	O1—C5—C6—C11	2.2 (3)
N4ⁱ—Ni1—N1—C2	−89.78 (14)	C4—C5—C6—C11	−176.77 (18)
N7ⁱ—Ni1—N1—C1	169.37 (15)	C11—C6—C7—C8	−0.5 (3)
N7—Ni1—N1—C1	−10.63 (15)	C5—C6—C7—C8	178.7 (2)
N4—Ni1—N1—C1	−101.08 (15)	C6—C7—C8—C9	0.1 (4)
N4ⁱ—Ni1—N1—C1	78.92 (15)	C7—C8—C9—C10	0.4 (4)
C2—N2—N3—C1	0.4 (2)	C8—C9—C10—C11	−0.6 (4)
C3—N2—N3—C1	175.77 (16)	C9—C10—C11—C6	0.2 (4)
N7ⁱ—Ni1—N4—C13	−19.91 (15)	C7—C6—C11—C10	0.3 (3)
N7—Ni1—N4—C13	160.09 (15)	C5—C6—C11—C10	−178.9 (2)
N1—Ni1—N4—C13	−110.27 (15)	N5—N6—C12—N4	−0.2 (2)
N1ⁱ—Ni1—N4—C13	69.73 (15)	C13—N4—C12—N6	0.5 (2)
N7ⁱ—Ni1—N4—C12	165.83 (16)	Ni1—N4—C12—N6	175.88 (13)
N7—Ni1—N4—C12	−14.17 (16)	C12—N4—C13—N5	−0.6 (2)
N1—Ni1—N4—C12	75.48 (16)	Ni1—N4—C13—N5	−176.09 (11)
N1ⁱ—Ni1—N4—C12	−104.52 (16)	N6—N5—C13—N4	0.5 (2)
C13—N5—N6—C12	−0.2 (2)	C14—N5—C13—N4	176.90 (16)
C14—N5—N6—C12	−176.91 (17)	C13—N5—C14—C15	128.03 (19)
N4—Ni1—N7—C23	32.2 (3)	N6—N5—C14—C15	−55.9 (2)
N4ⁱ—Ni1—N7—C23	−147.8 (3)	N5—C14—C15—C16	−177.37 (15)
N1—Ni1—N7—C23	−60.3 (3)	C14—C15—C16—O2	6.2 (3)
N1ⁱ—Ni1—N7—C23	119.7 (3)	C14—C15—C16—C17	−174.59 (16)
N2—N3—C1—N1	−0.2 (2)	O2—C16—C17—C18	173.0 (2)
C2—N1—C1—N3	−0.1 (2)	C15—C16—C17—C18	−6.3 (3)
Ni1—N1—C1—N3	−171.03 (12)	O2—C16—C17—C22	−6.5 (3)
N3—N2—C2—N1	−0.5 (2)	C15—C16—C17—C22	174.30 (17)
C3—N2—C2—N1	−175.28 (16)	C22—C17—C18—C19	1.5 (3)
C1—N1—C2—N2	0.33 (19)	C16—C17—C18—C19	−177.93 (19)
Ni1—N1—C2—N2	171.29 (11)	C17—C18—C19—C20	−1.3 (3)
C2—N2—C3—C4	−110.8 (2)	C18—C19—C20—C21	0.2 (4)
N3—N2—C3—C4	74.8 (2)	C19—C20—C21—C22	0.6 (4)
N2—C3—C4—C5	79.4 (2)	C20—C21—C22—C17	−0.4 (3)
C3—C4—C5—O1	1.3 (3)	C18—C17—C22—C21	−0.7 (3)
C3—C4—C5—C6	−179.74 (16)	C16—C17—C22—C21	178.80 (19)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(NCS)₂(C₁₁H₁₁N₃O)₄]
M_r	979.78
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8067 (10), 11.8539 (15), 13.8179 (17)
α, β, γ (°)	68.907 (2), 74.765 (2), 81.687 (2)
V (Å³)	1149.3 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.32 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.838, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	6289, 4016, 3540
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.080, 1.06
No. of reflections	4016
No. of parameters	304
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.34

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author gratefully acknowledges financial support from the Youthful Foundation of Tianjin Normal University (Natural Science, grant No. 52 L J44)

References

Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, J.-H. & Cai, H. (2007). Acta Cryst. E63, m1322–m1324. Web of Science CSD CrossRef IUCr Journals 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
Yue, Y. F., Gao, E. Q., Fang, C. J., Zheng, T., Liang, J. & Yan, C. H. (2008). Cryst. Growth Des. 9, 3295–3301. Web of Science CSD CrossRef Google Scholar

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