Aqua­[1-(pyrazin-2-yl)ethanone oximato-κ2N,N′][1-(pyrazin-2-yl)ethanone oxime-κ2N,N′](thio­cyanato-κN)nickel(II)

Pang, T.; Liu, J.-C.; Sun, Z.; Xiao, C.-H.; Cao, P.

doi:10.1107/S1600536812024622

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m883

https://doi.org/10.1107/S1600536812024622

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Aqua[1-(pyrazin-2-yl)ethanone oximato-κ²N,N′][1-(pyrazin-2-yl)ethanone oxime-κ²N,N′](thiocyanato-κN)nickel(II)

Ting Pang,^a Jia-Cheng Liu,^a ^* Zan Sun,^a Chao-Hu Xiao ^a and Ping Cao ^a

^aKey Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: jcliu8@163.com

(Received 28 May 2012; accepted 30 May 2012; online 13 June 2012)

In the title complex, [Ni(C₆H₆N₃O)(NCS)(C₆H₇N₃O)(H₂O)] or [Ni(mpko)(SCN)(mpkoH)(H₂O)] [where mpkoH = 1-(pyrazin-2-yl)ethanone oxime], the Ni^II cation is in a slightly distorted octahedral geometry, being coordinated in the equatorial plane by four N atoms from two different mpkoH ligands, one of which is deprotonated, and by one N atom from a thiocyanate anion and one O atom from a water molecule in the axial positions. There is an intramolecular O—H⋯O hydrogen bond involving the oxime units of the two ligands. In the crystal, a three-dimensional supramolecular architecture is formed by O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For magnetic properties of related oxime complexes, see: Escuer et al. (2010 ); Radek et al. (1999 , 2001 ); Spini (1973 ).

Experimental

Crystal data

[Ni(C₆H₆N₃O)(NCS)(C₆H₇N₃O)(H₂O)]
M_r = 408.09
Monoclinic, C c
a = 11.917 (8) Å
b = 11.899 (8) Å
c = 12.354 (8) Å
β = 108.220 (5)°
V = 1664.1 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 296 K
0.36 × 0.32 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.648, T_max = 0.701
5816 measured reflections
2809 independent reflections
2700 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.045
S = 1.05
2809 reflections
238 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1258 Friedel pairs
Flack parameter: 0.079 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O⋯O3	0.89 (4)	1.63 (4)	2.505 (3)	167 (5)
O1—H1W⋯N2ⁱ	0.82	2.14	2.941 (4)	166
O1—H2W⋯O3ⁱⁱ	0.89 (2)	1.84 (2)	2.690 (3)	161 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: https://doi.org/10.1107/S1600536812024622/su2441sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024622/su2441Isup2.hkl

checkCIF report

Comment top

In the past decades, much attention has been paid to the design and synthesis of oximes complexes. Oximes can be feasibly synthesized by the Schiff base condensation of an aldehyde or ketone with hydroxylamine. To date, various oximate ligands as bridging ligands have been extensively explored for their great ability to form homo- and heterometallic polynuclear complexes, which can transmit magnetic exchange efficiently (Radek et al. 1999, 2001). Among oximate bridging ligands, R-substituted-pyridyloximes, (py)C(R)NOH, salycylaldoximes and R-saoH₂ play an outstanding role to generate a great variety of polynuclear complexes which not only have aesthetically pleasing structures, but also possess interesting magnetic properties of single molecule magnet (SMM) and single chain magnet (SCM) behavior (Escuer et al., 2010; Spini, 1973).

The title compound, Fig. 1, is a new nickel complex obtained by the reaction of nickel chloride hexahydrate with mpkoH (methyl pyrazine-2-yl ketoxime) in CH₃OH solution. The Ni^II cation is in a slightly distorted octahedral geometry. The equatorial plane is defined by four N atoms from two mpkoH ligands - one of which is deprotonated, while the axial positions are occupied by one N atom from a SCN^- anion and one water O atom. There is an intramolecular O-H···O hydrogen bond (Table 1) involving the the oxime moieties of the two ligands.

In the crystal a three-dimensional supramolecular architecture is formed by O—H···O and O—H···N hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For magnetic properties of related oxime complexes, see: Escuer et al. (2010); Radek et al. (1999, 2001); Spini (1973).

Experimental top

The title complex was prepared by the addition of nickel chloride hexahydrate (23.9 mg, 0.1 mmol) to a CH₃OH solution of methyl pyrazine-2-yl ketoxime (28 mg, 0.2 mmol); the pH was adjusted to 8 with 1M KSCN. Slow evaporation of the solvent gave red block-like crystals of the title compound, suitable for X-ray analysis, after several days at room temperature [Yield 31 mg, 77%]. Anal. Calc. for C₁₃H₁₅N₇NiO₃S: C, 38.26; H, 3.71; N, 24.03. Found: C, 36.93; H, 3.4; N, 25.1%.

Structure description top

In the crystal a three-dimensional supramolecular architecture is formed by O—H···O and O—H···N hydrogen bonds (Fig. 2 and Table 1).

For magnetic properties of related oxime complexes, see: Escuer et al. (2010); Radek et al. (1999, 2001); Spini (1973).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. A view of the molecular structure of the title compound with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. The O-H···O and O-H···N hydrogen bonds are shown as dashed lines (see Table 1 for details).

Aqua[1-(pyrazin-2-yl)ethanone oximato-κ²N,N'][1-(pyrazin-2-yl)ethanone oxime-κ²N,N'](thiocyanato-κN)nickel(II) top

Crystal data top

[Ni(C₆H₆N₃O)(NCS)(C₆H₇N₃O)(H₂O)]	F(000) = 840
M_r = 408.09	D_x = 1.629 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4663 reflections
a = 11.917 (8) Å	θ = 2.5–28.9°
b = 11.899 (8) Å	µ = 1.32 mm⁻¹
c = 12.354 (8) Å	T = 296 K
β = 108.220 (5)°	Block, red
V = 1664.1 (19) Å³	0.36 × 0.32 × 0.29 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2809 independent reflections
Radiation source: fine-focus sealed tube	2700 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→14
T_min = 0.648, T_max = 0.701	k = −14→14
5816 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.020	w = 1/[σ²(F_o²) + (0.0195P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.045	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.22 e Å⁻³
2809 reflections	Δρ_min = −0.16 e Å⁻³
238 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
5 restraints	Extinction coefficient: 0.0035 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1258 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.079 (9)

Crystal data top

[Ni(C₆H₆N₃O)(NCS)(C₆H₇N₃O)(H₂O)]	V = 1664.1 (19) Å³
M_r = 408.09	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 11.917 (8) Å	µ = 1.32 mm⁻¹
b = 11.899 (8) Å	T = 296 K
c = 12.354 (8) Å	0.36 × 0.32 × 0.29 mm
β = 108.220 (5)°

Data collection top

Bruker APEXII CCD diffractometer	2809 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2700 reflections with I > 2σ(I)
T_min = 0.648, T_max = 0.701	R_int = 0.017
5816 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.045	Δρ_max = 0.22 e Å⁻³
S = 1.05	Δρ_min = −0.16 e Å⁻³
2809 reflections	Absolute structure: Flack (1983), 1258 Friedel pairs
238 parameters	Absolute structure parameter: 0.079 (9)
5 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.06769 (2)	0.04643 (2)	0.79647 (2)	0.0232 (1)
S1	−0.29404 (7)	0.01219 (7)	0.48705 (6)	0.0505 (3)
O1	0.22258 (19)	0.04631 (13)	0.93718 (17)	0.0297 (6)
O2	0.1754 (2)	0.19519 (17)	0.65847 (17)	0.0455 (7)
O3	0.21552 (17)	−0.01069 (15)	0.64998 (15)	0.0416 (6)
N1	−0.00488 (18)	0.17283 (15)	0.87702 (17)	0.0243 (6)
N2	−0.12050 (19)	0.35594 (17)	0.93569 (18)	0.0389 (7)
N3	0.11228 (18)	0.19306 (17)	0.73314 (18)	0.0291 (7)
N4	0.02311 (18)	−0.11543 (16)	0.83966 (17)	0.0308 (7)
N5	−0.0404 (2)	−0.33939 (18)	0.8492 (3)	0.0609 (10)
N6	0.14984 (18)	−0.05268 (16)	0.71043 (16)	0.0294 (6)
N7	−0.0897 (2)	0.04323 (17)	0.6682 (2)	0.0364 (9)
C1	−0.0646 (2)	0.1639 (2)	0.9510 (2)	0.0324 (8)
C2	−0.1229 (2)	0.2544 (2)	0.9789 (2)	0.0376 (8)
C3	−0.0582 (2)	0.36562 (18)	0.8631 (2)	0.0338 (8)
C4	−0.0003 (2)	0.27569 (18)	0.83197 (19)	0.0262 (7)
C5	0.0660 (2)	0.28514 (19)	0.7509 (2)	0.0309 (7)
C6	0.0749 (3)	0.3925 (2)	0.6917 (2)	0.0552 (12)
C7	−0.0488 (3)	−0.1484 (2)	0.8961 (2)	0.0452 (10)
C8	−0.0807 (3)	−0.2595 (3)	0.8998 (3)	0.0552 (11)
C9	0.0317 (3)	−0.3073 (2)	0.7932 (3)	0.0508 (10)
C10	0.0655 (3)	−0.19532 (16)	0.7858 (3)	0.0332 (7)
C11	0.1399 (2)	−0.1601 (2)	0.7182 (2)	0.0321 (8)
C12	0.1990 (3)	−0.2437 (2)	0.6627 (3)	0.0485 (10)
C13	−0.1750 (2)	0.03029 (18)	0.5946 (2)	0.0290 (8)
H1	−0.06730	0.09470	0.98520	0.0390*
H1O	0.200 (4)	0.125 (3)	0.654 (3)	0.092 (14)*
H1W	0.26870	−0.00070	0.92730	0.0450*
H2	−0.16540	0.24360	1.02960	0.0450*
H2W	0.207 (2)	0.0450 (19)	1.0028 (13)	0.053 (9)*
H3	−0.05340	0.43590	0.83190	0.0410*
H6A	0.13750	0.43750	0.74000	0.0830*
H6B	0.00160	0.43270	0.67490	0.0830*
H6C	0.09130	0.37630	0.62200	0.0830*
H7	−0.07890	−0.09500	0.93470	0.0540*
H8	−0.13260	−0.27820	0.93960	0.0660*
H9	0.06190	−0.36210	0.75640	0.0610*
H12A	0.14020	−0.28170	0.60260	0.0730*
H12B	0.24150	−0.29750	0.71840	0.0730*
H12C	0.25290	−0.20530	0.63180	0.0730*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0290 (2)	0.0193 (1)	0.0225 (1)	0.0021 (2)	0.0098 (1)	−0.0009 (2)
S1	0.0319 (4)	0.0722 (5)	0.0404 (4)	0.0037 (3)	0.0012 (3)	−0.0099 (3)
O1	0.0305 (11)	0.0341 (11)	0.0258 (11)	0.0046 (7)	0.0106 (9)	−0.0009 (7)
O2	0.0666 (14)	0.0386 (11)	0.0455 (12)	0.0003 (10)	0.0382 (11)	0.0025 (9)
O3	0.0520 (11)	0.0481 (10)	0.0342 (10)	0.0031 (9)	0.0270 (9)	−0.0049 (8)
N1	0.0280 (11)	0.0209 (10)	0.0245 (10)	0.0003 (8)	0.0089 (9)	0.0004 (8)
N2	0.0336 (12)	0.0374 (11)	0.0453 (13)	0.0056 (9)	0.0119 (10)	−0.0114 (10)
N3	0.0369 (13)	0.0269 (11)	0.0259 (10)	0.0019 (9)	0.0135 (9)	0.0008 (8)
N4	0.0342 (12)	0.0252 (11)	0.0340 (11)	−0.0011 (9)	0.0122 (9)	−0.0011 (9)
N5	0.0601 (17)	0.0271 (12)	0.088 (2)	−0.0061 (12)	0.0124 (16)	0.0101 (13)
N6	0.0315 (11)	0.0319 (10)	0.0236 (10)	0.0050 (9)	0.0071 (9)	−0.0050 (8)
N7	0.0376 (18)	0.0334 (14)	0.0363 (16)	0.0025 (9)	0.0087 (13)	−0.0069 (9)
C1	0.0346 (14)	0.0312 (13)	0.0341 (14)	−0.0014 (11)	0.0145 (12)	0.0001 (11)
C2	0.0380 (15)	0.0403 (14)	0.0385 (14)	0.0008 (11)	0.0178 (12)	−0.0066 (11)
C3	0.0327 (14)	0.0237 (12)	0.0423 (14)	0.0036 (10)	0.0080 (11)	0.0003 (10)
C4	0.0294 (13)	0.0204 (11)	0.0245 (12)	−0.0015 (10)	0.0024 (10)	−0.0019 (9)
C5	0.0380 (14)	0.0262 (12)	0.0284 (12)	−0.0024 (11)	0.0104 (11)	0.0008 (9)
C6	0.096 (3)	0.0296 (13)	0.0501 (18)	−0.0041 (14)	0.0375 (18)	0.0044 (12)
C7	0.0537 (19)	0.0355 (15)	0.0549 (18)	−0.0051 (13)	0.0291 (16)	0.0012 (12)
C8	0.053 (2)	0.0441 (18)	0.072 (2)	−0.0113 (16)	0.0244 (18)	0.0159 (16)
C9	0.055 (2)	0.0264 (12)	0.0639 (18)	0.0060 (11)	0.0084 (18)	−0.0039 (14)
C10	0.0328 (13)	0.0239 (10)	0.0367 (14)	0.0079 (14)	0.0019 (10)	−0.0015 (13)
C11	0.0321 (14)	0.0296 (13)	0.0293 (13)	0.0109 (11)	0.0021 (11)	−0.0053 (10)
C12	0.055 (2)	0.0380 (16)	0.0482 (17)	0.0155 (14)	0.0098 (15)	−0.0156 (13)
C13	0.0308 (15)	0.0275 (12)	0.0317 (13)	0.0049 (10)	0.0141 (12)	−0.0034 (9)

Geometric parameters (Å, º) top

Ni1—O1	2.103 (3)	N7—C13	1.143 (3)
Ni1—N1	2.130 (2)	C1—C2	1.382 (4)
Ni1—N3	2.049 (2)	C3—C4	1.391 (3)
Ni1—N4	2.110 (2)	C4—C5	1.461 (4)
Ni1—N6	2.032 (2)	C5—C6	1.492 (4)
Ni1—N7	2.043 (3)	C7—C8	1.380 (4)
S1—C13	1.627 (3)	C9—C10	1.403 (3)
O2—N3	1.361 (3)	C10—C11	1.457 (4)
O3—N6	1.336 (3)	C11—C12	1.503 (4)
O1—H1W	0.8200	C1—H1	0.9300
O1—H2W	0.887 (18)	C2—H2	0.9300
O2—H1O	0.89 (4)	C3—H3	0.9300
N1—C1	1.327 (3)	C6—H6A	0.9600
N1—C4	1.353 (3)	C6—H6B	0.9600
N2—C2	1.325 (3)	C6—H6C	0.9600
N2—C3	1.336 (3)	C7—H7	0.9300
N3—C5	1.276 (3)	C8—H8	0.9300
N4—C10	1.346 (4)	C9—H9	0.9300
N4—C7	1.322 (4)	C12—H12A	0.9600
N5—C9	1.317 (5)	C12—H12B	0.9600
N5—C8	1.309 (5)	C12—H12C	0.9600
N6—C11	1.290 (3)

O1—Ni1—N1	89.65 (8)	C3—C4—C5	123.5 (2)
O1—Ni1—N3	92.91 (8)	C4—C5—C6	122.6 (2)
O1—Ni1—N4	90.90 (7)	N3—C5—C4	114.0 (2)
O1—Ni1—N6	89.43 (8)	N3—C5—C6	123.4 (2)
O1—Ni1—N7	175.60 (9)	N4—C7—C8	122.2 (3)
N1—Ni1—N3	76.64 (8)	N5—C8—C7	122.3 (3)
N1—Ni1—N4	110.80 (8)	N5—C9—C10	123.9 (3)
N1—Ni1—N6	170.52 (8)	N4—C10—C9	118.6 (3)
N1—Ni1—N7	88.12 (9)	N4—C10—C11	118.0 (2)
N3—Ni1—N4	171.68 (8)	C9—C10—C11	123.3 (3)
N3—Ni1—N6	93.99 (8)	N6—C11—C12	123.7 (2)
N3—Ni1—N7	90.26 (9)	C10—C11—C12	121.8 (2)
N4—Ni1—N6	78.65 (8)	N6—C11—C10	114.5 (2)
N4—Ni1—N7	86.36 (8)	S1—C13—N7	178.2 (2)
N6—Ni1—N7	93.39 (9)	N1—C1—H1	119.00
Ni1—O1—H1W	109.00	C2—C1—H1	119.00
Ni1—O1—H2W	112.0 (15)	N2—C2—H2	119.00
H1W—O1—H2W	118.00	C1—C2—H2	119.00
N3—O2—H1O	107 (3)	N2—C3—H3	118.00
Ni1—N1—C4	111.85 (16)	C4—C3—H3	118.00
C1—N1—C4	117.1 (2)	C5—C6—H6A	109.00
Ni1—N1—C1	130.46 (15)	C5—C6—H6B	109.00
C2—N2—C3	115.8 (2)	C5—C6—H6C	109.00
O2—N3—C5	117.4 (2)	H6A—C6—H6B	110.00
Ni1—N3—C5	119.20 (18)	H6A—C6—H6C	109.00
Ni1—N3—O2	122.62 (15)	H6B—C6—H6C	109.00
Ni1—N4—C10	110.89 (18)	N4—C7—H7	119.00
C7—N4—C10	117.2 (2)	C8—C7—H7	119.00
Ni1—N4—C7	131.30 (17)	N5—C8—H8	119.00
C8—N5—C9	115.9 (3)	C7—C8—H8	119.00
Ni1—N6—O3	122.51 (14)	N5—C9—H9	118.00
Ni1—N6—C11	117.75 (17)	C10—C9—H9	118.00
O3—N6—C11	119.7 (2)	C11—C12—H12A	109.00
Ni1—N7—C13	173.0 (2)	C11—C12—H12B	109.00
N1—C1—C2	122.0 (2)	C11—C12—H12C	110.00
N2—C2—C1	122.3 (2)	H12A—C12—H12B	110.00
N2—C3—C4	123.2 (2)	H12A—C12—H12C	110.00
N1—C4—C3	119.7 (2)	H12B—C12—H12C	110.00
N1—C4—C5	116.9 (2)

O1—Ni1—N1—C1	−86.7 (2)	C1—N1—C4—C5	179.8 (2)
N3—Ni1—N1—C1	−179.7 (2)	Ni1—N1—C4—C3	171.17 (18)
N4—Ni1—N1—C1	4.2 (2)	C1—N1—C4—C3	−0.8 (3)
N7—Ni1—N1—C1	89.6 (2)	C2—N2—C3—C4	1.0 (4)
O1—Ni1—N1—C4	102.77 (17)	C3—N2—C2—C1	0.1 (4)
N3—Ni1—N1—C4	9.69 (16)	Ni1—N3—C5—C6	−168.53 (19)
N4—Ni1—N1—C4	−166.41 (16)	O2—N3—C5—C6	1.9 (4)
N7—Ni1—N1—C4	−81.03 (17)	Ni1—N3—C5—C4	9.5 (3)
O1—Ni1—N3—O2	90.31 (19)	O2—N3—C5—C4	179.9 (2)
N1—Ni1—N3—O2	179.3 (2)	C10—N4—C7—C8	−0.5 (4)
N6—Ni1—N3—O2	0.7 (2)	Ni1—N4—C10—C11	5.1 (3)
N7—Ni1—N3—O2	−92.7 (2)	C7—N4—C10—C11	176.8 (3)
O1—Ni1—N3—C5	−99.8 (2)	C7—N4—C10—C9	−0.3 (4)
N1—Ni1—N3—C5	−10.86 (19)	Ni1—N4—C7—C8	169.3 (2)
N6—Ni1—N3—C5	170.6 (2)	Ni1—N4—C10—C9	−172.1 (3)
N7—Ni1—N3—C5	77.2 (2)	C8—N5—C9—C10	−0.1 (5)
O1—Ni1—N4—C7	97.6 (2)	C9—N5—C8—C7	−0.7 (5)
N1—Ni1—N4—C7	7.7 (3)	Ni1—N6—C11—C12	−177.9 (2)
N6—Ni1—N4—C7	−173.1 (2)	O3—N6—C11—C10	−179.7 (2)
N7—Ni1—N4—C7	−78.9 (2)	O3—N6—C11—C12	0.2 (4)
O1—Ni1—N4—C10	−92.1 (2)	Ni1—N6—C11—C10	2.3 (3)
N1—Ni1—N4—C10	177.9 (2)	N1—C1—C2—N2	−1.6 (4)
N6—Ni1—N4—C10	−2.9 (2)	N2—C3—C4—N1	−0.7 (4)
N7—Ni1—N4—C10	91.3 (2)	N2—C3—C4—C5	178.7 (2)
O1—Ni1—N6—O3	−86.70 (18)	N1—C4—C5—N3	−0.2 (3)
N3—Ni1—N6—O3	6.18 (18)	N1—C4—C5—C6	177.9 (2)
N4—Ni1—N6—O3	−177.73 (19)	C3—C4—C5—C6	−1.6 (4)
N7—Ni1—N6—O3	96.68 (18)	C3—C4—C5—N3	−179.7 (2)
O1—Ni1—N6—C11	91.28 (18)	N4—C7—C8—N5	1.1 (5)
N3—Ni1—N6—C11	−175.84 (19)	N5—C9—C10—C11	−176.4 (3)
N4—Ni1—N6—C11	0.25 (18)	N5—C9—C10—N4	0.6 (5)
N7—Ni1—N6—C11	−85.35 (19)	N4—C10—C11—C12	175.1 (3)
Ni1—N1—C1—C2	−168.28 (18)	C9—C10—C11—N6	171.9 (3)
C4—N1—C1—C2	1.9 (4)	C9—C10—C11—C12	−7.9 (5)
Ni1—N1—C4—C5	−8.3 (3)	N4—C10—C11—N6	−5.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···O3	0.89 (4)	1.63 (4)	2.505 (3)	167 (5)
O1—H1W···N2ⁱ	0.82	2.14	2.941 (4)	166
O1—H2W···O3ⁱⁱ	0.89 (2)	1.84 (2)	2.690 (3)	161 (2)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₆H₆N₃O)(NCS)(C₆H₇N₃O)(H₂O)]
M_r	408.09
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	11.917 (8), 11.899 (8), 12.354 (8)
β (°)	108.220 (5)
V (Å³)	1664.1 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.36 × 0.32 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.648, 0.701
No. of measured, independent and observed [I > 2σ(I)] reflections	5816, 2809, 2700
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.045, 1.05
No. of reflections	2809
No. of parameters	238
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16
Absolute structure	Flack (1983), 1258 Friedel pairs
Absolute structure parameter	0.079 (9)

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···O3	0.89 (4)	1.63 (4)	2.505 (3)	167 (5)
O1—H1W···N2ⁱ	0.82	2.14	2.941 (4)	166
O1—H2W···O3ⁱⁱ	0.887 (18)	1.835 (17)	2.690 (3)	161 (2)

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

Acknowledgements

The authors thank the National Natural Science Foundation (No. 20871099) of China, the Natural Science Foundation of Gansu Province (No. 0710RJZA113), the NWNU-LKQN-10–14 Foundation and the Key Laboratory of Eco-Environment-Related Polymer Materials (Northwest Normal University), Ministry of Education, for financial support.

References

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Radek, C., Ivana, C., Jan, O., František, L. & Jiří, L. (2001). Collect. Czech. Chem. Commun. 66, 170–184. Google Scholar
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