(Methanol-κO){1-[2-(piperazin-4-ium-1-yl-κN1)ethyl­imino­methyl-κN]naphthalen-2-olato-κO}bis­(thio­cyanato-κN)nickel(II) methanol monosolvate

Li, P.-A.

doi:10.1107/S1600536812013773

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m549

doi:10.1107/S1600536812013773

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(Methanol-κO){1-[2-(piperazin-4-ium-1-yl-κN¹)ethyliminomethyl-κN]naphthalen-2-olato-κO}bis(thiocyanato-κN)nickel(II) methanol monosolvate

Pin-Ai Li ^a ^*

^aLuohe Medical College, Luohe Henan 462002, People's Republic of China
^*Correspondence e-mail: li_pinai@126.com

(Received 27 March 2012; accepted 30 March 2012; online 4 April 2012)

In the title solvated complex, [Ni(C₁₇H₂₁N₃O)(NCS)₂(CH₃OH)]·CH₃OH, the Ni²⁺ ion is coordinated by one phenolate O, one imine N, and one amine N atom of the tridentate Schiff base ligand, two thiocyanate N atoms and one methanol O atom, resulting in a distorted cis-NiO₂N₄ octahedral geometry. The chelate ring formed by the phenolate O and imine N atoms approximates to an envelope with the Ni atom as the flap, whereas the chelate ring formed by the two N atoms is twisted about the C—C bond. In the crystal, the components are linked by O—H⋯O, N—H⋯O, N—H⋯S, and O—H⋯S hydrogen bonds.

Related literature

For background to the biological properties of nickel complexes of Schiff bases, see: Chohan & Kausar (1993 ); Osowole et al. (2008 ); Arif et al. (2011 ). For related structures, see: Ji & Lu (2010 ); Wang (2010 ); Xue et al. (2010 ).

Experimental

Crystal data

[Ni(C₁₇H₂₁N₃O)(NCS)₂(CH₄O)]·CH₄O
M_r = 522.32
Monoclinic, P 2₁ /c
a = 9.7420 (19) Å
b = 15.304 (3) Å
c = 18.302 (5) Å
β = 116.01 (2)°
V = 2452.3 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.849, T_max = 0.865
16581 measured reflections
4196 independent reflections
2354 reflections with I > 2σ(I)
R_int = 0.153

Refinement

R[F² > 2σ(F²)] = 0.092
wR(F²) = 0.209
S = 1.00
4196 reflections
295 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	1.997 (6)
Ni1—N3	2.044 (7)
Ni1—O1	2.049 (5)
Ni1—N4	2.064 (7)
Ni1—O2	2.128 (7)
Ni1—N2	2.241 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82 (1)	2.03 (4)	2.793 (10)	155 (10)
N5—H5B⋯O1ⁱ	0.90	1.75	2.649 (8)	175
N5—H5A⋯S2ⁱⁱ	0.90	2.67	3.480 (7)	150
O3—H3⋯S2ⁱⁱ	0.82	2.78	3.532 (9)	154
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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/S1600536812013773/hb6710sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013773/hb6710Isup2.hkl

checkCIF report

Comment top

Soem nickel complexes derived from Schiff bases have possess interesting biological properties (Arif et al., 2011; Osowole et al., 2008; Chohan & Kausar, 1993). As an extension of the work on the structures of such complexes, the author reports herein the title new nickel complex.

The title compound contains a mononuclear nickel complex molecule and a methanol molecule of crystallization (Fig. 1). The Ni atom in the complex is coordinated by one phenolate O, one imine N, and one amine N atom of the Schiff base ligand, two thiocyanate N atoms, and one methanol O atom, forming an octahedral coordination. The bond lengths (Table 1) are comparable to those reported in the similar nickel complexes with Schiff bases (Wang, 2010; Ji & Lu, 2010; Xue et al., 2010). The crystal structure features N—H···O, N—H···S, and O—H···S hydrogen bonds (Table 2, Fig. 2).

Related literature top

For background to the biological properties of nickel complexes of Schiff bases, see: Chohan & Kausar (1993); Osowole et al. (2008); Arif et al. (2011). For related structures, see: Ji & Lu (2010); Wang (2010); Xue et al. (2010).

Experimental top

2-Hydroxy-1-naphthaldehyde (1.72 g, 0.01 mol) and 2-piperazin-1-ylethyamine (1.29 g, 0.01 mol) were mixed in methanol (30 ml). To the stirred mixture was added a methanolic solution (10 ml) of ammonium thiocyanate (1.52 g, 0.02 mol) and a methanolic solution (10 ml) of nickel nitrate (2.91 g, 0.01 mol). The final mixture was further stirred for 30 min to give a green solution. Green block-like single crystals were obtained by slow evaporation of the solution in air.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 structure of the title compound, with displacement ellipsoids drawn at the 30% probability level for Non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

(Methanol-κO){1-[2-(piperazin-4-ium-1-yl- κN¹)ethyliminomethyl-κN]naphthalen-2-olato- κO}bis(thiocyanato-κN)nickel(II) methanol monosolvate top

Crystal data top

[Ni(C₁₇H₂₁N₃O)(NCS)₂(CH₄O)]·CH₄O	F(000) = 1096
M_r = 522.32	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7420 (19) Å	Cell parameters from 888 reflections
b = 15.304 (3) Å	θ = 2.3–24.5°
c = 18.302 (5) Å	µ = 0.99 mm⁻¹
β = 116.01 (2)°	T = 298 K
V = 2452.3 (10) Å³	Block, green
Z = 4	0.17 × 0.15 × 0.15 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	4196 independent reflections
Radiation source: fine-focus sealed tube	2354 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.153
ω scan	θ_max = 25.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −11→11
T_min = 0.849, T_max = 0.865	k = −18→18
16581 measured reflections	l = −21→21

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0864P)²] where P = (F_o² + 2F_c²)/3
4196 reflections	(Δ/σ)_max < 0.001
295 parameters	Δρ_max = 1.05 e Å⁻³
1 restraint	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Ni(C₁₇H₂₁N₃O)(NCS)₂(CH₄O)]·CH₄O	V = 2452.3 (10) Å³
M_r = 522.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7420 (19) Å	µ = 0.99 mm⁻¹
b = 15.304 (3) Å	T = 298 K
c = 18.302 (5) Å	0.17 × 0.15 × 0.15 mm
β = 116.01 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4196 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2354 reflections with I > 2σ(I)
T_min = 0.849, T_max = 0.865	R_int = 0.153
16581 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.092	1 restraint
wR(F²) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 1.05 e Å⁻³
4196 reflections	Δρ_min = −0.47 e Å⁻³
295 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	0.08725 (12)	0.32345 (6)	0.35614 (6)	0.0356 (3)
S1	−0.3385 (3)	0.40557 (18)	0.11040 (14)	0.0662 (8)
S2	−0.1939 (3)	0.23841 (17)	0.50772 (14)	0.0641 (8)
O1	0.1635 (7)	0.4331 (3)	0.4268 (3)	0.0465 (15)
O2	0.2267 (8)	0.3634 (4)	0.2996 (4)	0.0612 (17)
O3	0.0875 (10)	0.4095 (6)	0.1353 (4)	0.097 (3)
H3	0.0055	0.3840	0.1128	0.145*
N1	0.2670 (7)	0.2604 (4)	0.4397 (4)	0.0437 (18)
N2	0.0484 (7)	0.1938 (4)	0.2933 (4)	0.0348 (15)
N3	−0.0853 (8)	0.3835 (4)	0.2599 (4)	0.0488 (19)
N4	−0.0474 (8)	0.2903 (4)	0.4131 (4)	0.0412 (17)
N5	−0.1175 (7)	0.0886 (4)	0.1435 (4)	0.0450 (18)
H5A	−0.1729	0.1302	0.1080	0.054*
H5B	−0.1389	0.0370	0.1173	0.054*
C1	0.3224 (8)	0.3598 (5)	0.5527 (4)	0.0374 (19)
C2	0.2355 (9)	0.4313 (5)	0.5085 (5)	0.041 (2)
C3	0.2202 (10)	0.5057 (6)	0.5479 (5)	0.053 (2)
H3A	0.1582	0.5512	0.5174	0.063*
C4	0.2957 (11)	0.5132 (6)	0.6318 (5)	0.054 (2)
H4	0.2873	0.5643	0.6569	0.065*
C5	0.3847 (9)	0.4438 (5)	0.6788 (5)	0.043 (2)
C6	0.4632 (11)	0.4468 (7)	0.7668 (5)	0.058 (3)
H6	0.4564	0.4978	0.7926	0.070*
C7	0.5449 (10)	0.3806 (7)	0.8133 (5)	0.054 (3)
H7	0.5940	0.3861	0.8696	0.065*
C8	0.5545 (10)	0.3047 (7)	0.7763 (5)	0.060 (3)
H8	0.6101	0.2581	0.8082	0.072*
C9	0.4832 (9)	0.2953 (6)	0.6919 (5)	0.046 (2)
H9	0.4903	0.2426	0.6685	0.055*
C10	0.3988 (9)	0.3667 (6)	0.6409 (4)	0.042 (2)
C11	0.3444 (11)	0.2811 (5)	0.5145 (5)	0.052 (2)
H11	0.4209	0.2428	0.5471	0.062*
C12	0.2999 (10)	0.1768 (6)	0.4112 (5)	0.055 (3)
H12A	0.3612	0.1398	0.4570	0.066*
H12B	0.3554	0.1865	0.3790	0.066*
C13	0.1465 (10)	0.1340 (5)	0.3598 (5)	0.049 (2)
H13A	0.1623	0.0800	0.3367	0.059*
H13B	0.0960	0.1199	0.3937	0.059*
C14	0.0892 (9)	0.1941 (5)	0.2235 (4)	0.040 (2)
H14A	0.1981	0.2043	0.2441	0.048*
H14B	0.0366	0.2421	0.1875	0.048*
C15	0.0481 (10)	0.1082 (5)	0.1741 (5)	0.043 (2)
H15A	0.0732	0.1135	0.1285	0.052*
H15B	0.1076	0.0606	0.2082	0.052*
C16	−0.1588 (10)	0.0854 (5)	0.2119 (5)	0.048 (2)
H16A	−0.1049	0.0375	0.2478	0.058*
H16B	−0.2675	0.0745	0.1912	0.058*
C17	−0.1185 (10)	0.1709 (5)	0.2595 (5)	0.048 (2)
H17A	−0.1780	0.2177	0.2242	0.057*
H17B	−0.1467	0.1665	0.3040	0.057*
C18	−0.1908 (10)	0.3914 (5)	0.1988 (5)	0.0382 (19)
C19	−0.1038 (10)	0.2711 (5)	0.4529 (5)	0.041 (2)
C20	0.3836 (12)	0.3845 (8)	0.3386 (7)	0.087 (4)
H20A	0.3976	0.4441	0.3269	0.130*
H20B	0.4389	0.3466	0.3192	0.130*
H20C	0.4208	0.3773	0.3962	0.130*
C22	0.1608 (19)	0.4057 (12)	0.0882 (9)	0.148 (7)
H22A	0.1522	0.4610	0.0618	0.222*
H22B	0.1160	0.3609	0.0480	0.222*
H22C	0.2666	0.3925	0.1212	0.222*
H2	0.189 (11)	0.361 (7)	0.2499 (8)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0411 (6)	0.0276 (5)	0.0256 (5)	0.0056 (5)	0.0031 (4)	0.0015 (4)
S1	0.0644 (17)	0.0600 (17)	0.0413 (14)	0.0051 (13)	−0.0072 (12)	−0.0074 (12)
S2	0.084 (2)	0.0604 (17)	0.0447 (14)	−0.0249 (14)	0.0252 (14)	−0.0107 (12)
O1	0.077 (4)	0.017 (3)	0.028 (3)	0.012 (3)	0.006 (3)	0.002 (2)
O2	0.062 (5)	0.062 (4)	0.051 (4)	−0.018 (3)	0.017 (4)	−0.021 (4)
O3	0.100 (7)	0.124 (8)	0.056 (5)	−0.019 (6)	0.025 (5)	−0.004 (5)
N1	0.047 (4)	0.042 (4)	0.025 (4)	0.013 (3)	0.000 (3)	−0.008 (3)
N2	0.045 (4)	0.026 (4)	0.027 (3)	0.006 (3)	0.010 (3)	0.002 (3)
N3	0.052 (5)	0.040 (4)	0.038 (4)	0.006 (3)	0.005 (4)	0.004 (3)
N4	0.058 (5)	0.034 (4)	0.031 (4)	0.011 (3)	0.019 (4)	−0.004 (3)
N5	0.053 (5)	0.034 (4)	0.035 (4)	0.009 (3)	0.007 (4)	−0.002 (3)
C1	0.033 (5)	0.030 (4)	0.029 (4)	0.002 (4)	−0.005 (4)	−0.001 (3)
C2	0.045 (5)	0.032 (5)	0.033 (5)	−0.003 (4)	0.005 (4)	0.001 (4)
C3	0.068 (7)	0.034 (5)	0.054 (6)	0.007 (4)	0.025 (5)	−0.001 (4)
C4	0.072 (7)	0.039 (5)	0.038 (5)	0.020 (5)	0.012 (5)	−0.001 (4)
C5	0.043 (5)	0.043 (5)	0.040 (5)	−0.009 (4)	0.014 (4)	−0.015 (4)
C6	0.059 (6)	0.072 (7)	0.040 (5)	−0.005 (5)	0.018 (5)	−0.006 (5)
C7	0.059 (6)	0.074 (8)	0.029 (5)	−0.019 (5)	0.018 (5)	−0.010 (5)
C8	0.043 (6)	0.082 (8)	0.043 (6)	0.004 (5)	0.008 (5)	0.019 (5)
C9	0.051 (6)	0.052 (6)	0.026 (4)	−0.008 (4)	0.009 (4)	0.007 (4)
C10	0.037 (5)	0.049 (5)	0.027 (4)	0.001 (4)	0.001 (4)	−0.004 (4)
C11	0.062 (6)	0.035 (5)	0.048 (6)	0.019 (4)	0.013 (5)	0.007 (4)
C12	0.056 (6)	0.049 (5)	0.030 (5)	0.031 (5)	−0.009 (4)	−0.009 (4)
C13	0.080 (7)	0.030 (5)	0.037 (5)	0.005 (4)	0.024 (5)	−0.005 (4)
C14	0.044 (5)	0.021 (4)	0.034 (4)	0.000 (3)	−0.001 (4)	−0.004 (3)
C15	0.052 (6)	0.037 (5)	0.040 (5)	−0.004 (4)	0.019 (4)	−0.007 (4)
C16	0.042 (5)	0.036 (5)	0.054 (6)	−0.011 (4)	0.010 (4)	−0.010 (4)
C17	0.062 (6)	0.024 (4)	0.057 (6)	−0.005 (4)	0.026 (5)	−0.006 (4)
C18	0.050 (5)	0.023 (4)	0.038 (5)	0.006 (4)	0.015 (4)	0.002 (4)
C19	0.048 (6)	0.044 (5)	0.028 (5)	0.006 (4)	0.012 (4)	−0.008 (4)
C20	0.056 (7)	0.104 (10)	0.104 (9)	−0.015 (7)	0.040 (7)	−0.002 (8)
C22	0.141 (14)	0.199 (19)	0.132 (13)	−0.042 (13)	0.085 (13)	−0.032 (13)

Geometric parameters (Å, º) top

Ni1—N1	1.997 (6)	C5—C10	1.406 (11)
Ni1—N3	2.044 (7)	C5—C6	1.450 (11)
Ni1—O1	2.049 (5)	C6—C7	1.337 (12)
Ni1—N4	2.064 (7)	C6—H6	0.9300
Ni1—O2	2.128 (7)	C7—C8	1.369 (12)
Ni1—N2	2.241 (6)	C7—H7	0.9300
S1—C18	1.641 (9)	C8—C9	1.396 (11)
S2—C19	1.673 (10)	C8—H8	0.9300
O1—C2	1.344 (9)	C9—C10	1.438 (11)
O2—C20	1.411 (11)	C9—H9	0.9300
O2—H2	0.818 (10)	C11—H11	0.9300
O3—C22	1.339 (13)	C12—C13	1.521 (12)
O3—H3	0.8200	C12—H12A	0.9700
N1—C11	1.281 (10)	C12—H12B	0.9700
N1—C12	1.468 (9)	C13—H13A	0.9700
N2—C13	1.487 (9)	C13—H13B	0.9700
N2—C14	1.495 (9)	C14—C15	1.546 (10)
N2—C17	1.505 (10)	C14—H14A	0.9700
N3—C18	1.146 (9)	C14—H14B	0.9700
N4—C19	1.128 (9)	C15—H15A	0.9700
N5—C16	1.473 (9)	C15—H15B	0.9700
N5—C15	1.488 (10)	C16—C17	1.525 (10)
N5—H5A	0.9000	C16—H16A	0.9700
N5—H5B	0.9000	C16—H16B	0.9700
C1—C2	1.403 (10)	C17—H17A	0.9700
C1—C10	1.454 (10)	C17—H17B	0.9700
C1—C11	1.455 (11)	C20—H20A	0.9600
C2—C3	1.390 (11)	C20—H20B	0.9600
C3—C4	1.386 (12)	C20—H20C	0.9600
C3—H3A	0.9300	C22—H22A	0.9600
C4—C5	1.402 (11)	C22—H22B	0.9600
C4—H4	0.9300	C22—H22C	0.9600

N1—Ni1—N3	172.3 (3)	C9—C8—H8	119.1
N1—Ni1—O1	87.7 (2)	C8—C9—C10	120.4 (8)
N3—Ni1—O1	96.3 (2)	C8—C9—H9	119.8
N1—Ni1—N4	91.9 (3)	C10—C9—H9	119.8
N3—Ni1—N4	94.6 (3)	C5—C10—C9	118.0 (7)
O1—Ni1—N4	91.0 (2)	C5—C10—C1	119.7 (7)
N1—Ni1—O2	88.8 (3)	C9—C10—C1	122.3 (7)
N3—Ni1—O2	84.9 (3)	N1—C11—C1	125.3 (8)
O1—Ni1—O2	86.6 (2)	N1—C11—H11	117.4
N4—Ni1—O2	177.4 (2)	C1—C11—H11	117.4
N1—Ni1—N2	81.9 (2)	N1—C12—C13	106.7 (7)
N3—Ni1—N2	93.8 (2)	N1—C12—H12A	110.4
O1—Ni1—N2	169.1 (2)	C13—C12—H12A	110.4
N4—Ni1—N2	92.3 (2)	N1—C12—H12B	110.4
O2—Ni1—N2	90.3 (2)	C13—C12—H12B	110.4
C2—O1—Ni1	123.5 (4)	H12A—C12—H12B	108.6
C20—O2—Ni1	126.9 (6)	N2—C13—C12	110.2 (7)
C20—O2—H2	116 (8)	N2—C13—H13A	109.6
Ni1—O2—H2	117 (7)	C12—C13—H13A	109.6
C22—O3—H3	109.5	N2—C13—H13B	109.6
C11—N1—C12	118.5 (7)	C12—C13—H13B	109.6
C11—N1—Ni1	127.3 (6)	H13A—C13—H13B	108.1
C12—N1—Ni1	113.8 (5)	N2—C14—C15	113.6 (6)
C13—N2—C14	112.6 (6)	N2—C14—H14A	108.9
C13—N2—C17	112.5 (6)	C15—C14—H14A	108.9
C14—N2—C17	107.1 (6)	N2—C14—H14B	108.9
C13—N2—Ni1	102.8 (4)	C15—C14—H14B	108.9
C14—N2—Ni1	112.8 (4)	H14A—C14—H14B	107.7
C17—N2—Ni1	109.0 (4)	N5—C15—C14	110.6 (6)
C18—N3—Ni1	159.3 (7)	N5—C15—H15A	109.5
C19—N4—Ni1	171.1 (7)	C14—C15—H15A	109.5
C16—N5—C15	110.0 (6)	N5—C15—H15B	109.5
C16—N5—H5A	109.7	C14—C15—H15B	109.5
C15—N5—H5A	109.7	H15A—C15—H15B	108.1
C16—N5—H5B	109.7	N5—C16—C17	111.0 (7)
C15—N5—H5B	109.7	N5—C16—H16A	109.4
H5A—N5—H5B	108.2	C17—C16—H16A	109.4
C2—C1—C10	118.0 (7)	N5—C16—H16B	109.4
C2—C1—C11	123.1 (7)	C17—C16—H16B	109.4
C10—C1—C11	118.8 (7)	H16A—C16—H16B	108.0
O1—C2—C3	115.9 (7)	N2—C17—C16	113.3 (6)
O1—C2—C1	123.2 (7)	N2—C17—H17A	108.9
C3—C2—C1	120.9 (7)	C16—C17—H17A	108.9
C4—C3—C2	121.1 (8)	N2—C17—H17B	108.9
C4—C3—H3A	119.4	C16—C17—H17B	108.9
C2—C3—H3A	119.4	H17A—C17—H17B	107.7
C3—C4—C5	120.2 (8)	N3—C18—S1	177.8 (8)
C3—C4—H4	119.9	N4—C19—S2	176.6 (8)
C5—C4—H4	119.9	O2—C20—H20A	109.5
C4—C5—C10	120.0 (7)	O2—C20—H20B	109.5
C4—C5—C6	122.8 (8)	H20A—C20—H20B	109.5
C10—C5—C6	117.2 (8)	O2—C20—H20C	109.5
C7—C6—C5	124.1 (9)	H20A—C20—H20C	109.5
C7—C6—H6	118.0	H20B—C20—H20C	109.5
C5—C6—H6	118.0	O3—C22—H22A	109.5
C6—C7—C8	118.6 (8)	O3—C22—H22B	109.5
C6—C7—H7	120.7	H22A—C22—H22B	109.5
C8—C7—H7	120.7	O3—C22—H22C	109.5
C7—C8—C9	121.8 (9)	H22A—C22—H22C	109.5
C7—C8—H8	119.1	H22B—C22—H22C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82 (1)	2.03 (4)	2.793 (10)	155 (10)
N5—H5B···O1ⁱ	0.90	1.75	2.649 (8)	175
N5—H5A···S2ⁱⁱ	0.90	2.67	3.480 (7)	150
O3—H3···S2ⁱⁱ	0.82	2.78	3.532 (9)	154

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₇H₂₁N₃O)(NCS)₂(CH₄O)]·CH₄O
M_r	522.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.7420 (19), 15.304 (3), 18.302 (5)
β (°)	116.01 (2)
V (Å³)	2452.3 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.849, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	16581, 4196, 2354
R_int	0.153
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.092, 0.209, 1.00
No. of reflections	4196
No. of parameters	295
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.47

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—N1	1.997 (6)	Ni1—N4	2.064 (7)
Ni1—N3	2.044 (7)	Ni1—O2	2.128 (7)
Ni1—O1	2.049 (5)	Ni1—N2	2.241 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.818 (10)	2.03 (4)	2.793 (10)	155 (10)
N5—H5B···O1ⁱ	0.90	1.75	2.649 (8)	175
N5—H5A···S2ⁱⁱ	0.90	2.67	3.480 (7)	150
O3—H3···S2ⁱⁱ	0.82	2.78	3.532 (9)	154

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

The author acknowledges the Luohe Medical College for support.

References

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