[N-(8-Quinolylmeth­yl)imino­diethanol-κ4N,N′,O,O′]bis­(thio­cyanato-κN)nickel(II) monohydrate

Song, R.-F.; Wang, Y.-H.

doi:10.1107/S1600536807062526

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m12

https://doi.org/10.1107/S1600536807062526

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[N-(8-Quinolylmethyl)iminodiethanol-κ⁴N,N′,O,O′]bis(thiocyanato-κN)nickel(II) monohydrate

Rui-Feng Song ^a ^* and Yu-Hong Wang ^a

^aDepartment of Chemistry and Chemical Engineering, University of Science and Technology of Suzhou, Suzhou 215009, People's Republic of China
^*Correspondence e-mail: songrf@mail.usts.edu.cn

(Received 1 November 2007; accepted 23 November 2007; online 6 December 2007)

In the neutral title complex, [Ni(NCS)₂(C₁₄H₁₈N₂O₂)]·H₂O, the Ni^II ion has a distorted octahedral geometry with cis-isothiocyanate ligands.

Related literature

For diethanolamine and N-substituted diethanolamine transition metal coordination compounds, see: Saalfrank et al. (2001 ); Yilmaz et al. (2000 ).

Experimental

Crystal data

[Ni(NCS)₂(C₁₄H₁₈N₂O₂)]·H₂O
M_r = 439.19
Monoclinic, P 2₁ /c
a = 14.693 (6) Å
b = 10.142 (4) Å
c = 13.965 (6) Å
β = 115.460 (6)°
V = 1878.9 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 293 (2) K
0.15 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.800, T_max = 1.000 (expected range = 0.722–0.903)
8517 measured reflections
3783 independent reflections
2673 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.097
S = 1.08
3783 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—N3	2.011 (3)
Ni1—N4	2.018 (3)
Ni1—N2	2.061 (3)
Ni1—O2	2.067 (2)
Ni1—O1	2.089 (2)
Ni1—N1	2.093 (3)

N3—Ni1—N4	96.64 (12)
N3—Ni1—N2	97.00 (11)
N3—Ni1—O2	89.15 (12)
N4—Ni1—O2	91.29 (11)
N2—Ni1—O2	79.51 (10)
N4—Ni1—O1	85.70 (10)
N2—Ni1—O1	80.54 (10)
O2—Ni1—O1	89.84 (10)
N3—Ni1—N1	90.10 (12)
N4—Ni1—N1	96.35 (11)
N2—Ni1—N1	93.04 (10)
O1—Ni1—N1	90.59 (10)

Data collection: SMART (Bruker, 1998 ); cell refinement: SMART; data reduction: SAINT (Bruker, 1999 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062526/sg2198sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062526/sg2198Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, (I) is a neutral mononuclear complex, consisting of one nickel(II) ion, one N-(8-quinolylmethyl)iminodiethanol ligand, two SCN^- and one uncoordinated H₂O molecule. Each Ni^II center has a distorted octahedral geometry (Table 1) comprised of two isothiocyanate N atoms, the quinoline N donor, the tertiary N donor and two O donor of the ligand. The NSC groups are almost linear [178.9 (3)° and 178.2 (4)°], though he Ni—N—C linkage [158.8 (3)° and 171.5 (3)°] is bent. No intermolecular hydrogen bonds interactions were observed in the complex.

Related literature top

For diethanolamine and N-substituted diethanolamine transition metal coordination compounds of various structures, see: Saalfrank et al. (2001); Yilmaz et al. (2000).

Experimental top

Synthesis of the N-(8-quinolylmethyl)iminodiethanol ligand. 8-bromomethylquinoline (0.01 mol) was added to the solution of diethanolamine (0.03 mol) in ethanol (50 ml) with stirring. The mixture was refluxed for 15 h, and the solvent was evaporated. The residual oil was dissolved in 10 ml H₂O, and the mixture was extracted with benzene and dried over MgSO₄. The solvent was evaporated to give a pale yellow liquid, 1.92 g (78% yield). IR (cm^-1): 3357vs, 2926 s, 2869 s, 1454 s, 1425m, 1321m, 1130m, 1071 s, 1438 s, 834m. ¹H NMR (CDCl₃): 4.21 (2H,S,-CH₂Ar), 8.88 (1H, d, Ar—H2), 7.41 (1H, t, Ar—H3), 8.16 (1H, d, Ar—H4), 7.75 (1H, d, Ar—H5), 7.47(1H, t, Ar—H6), 7.57 (1H, d, Ar—H7), 2.74 (4H, t, NCH2C), 3.62 (4H, t, CH₂O), 1.25 (2H, s, OH). Anal. Found: C, 68.51; H, 7.62; N, 11.39%; calculated for C₁₄H₁₈N₂O₂: C, 68.27; H, 7.37; N, 11.37.

Synthesis of the title complex (I). Solid KSCN (0.2 mmol) was added slowly with continuous stirring to a solution of NiSO₄.6H₂O (0.1 mmol) in distilled water (15 ml), the ligand (0.1 mmol) was dissolved in methanol (15 ml) and two solutions were mixed. The mixture was filtered, and green crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from the resulting solution at room temperature. Anal. Found: C, 43.28; H, 4.63; N, 12.78%; calculated for C₁₆H₂₀N₄NiO₃S₂: C, 43.76; H, 4.59; N, 12.76%.

Structure description top

For diethanolamine and N-substituted diethanolamine transition metal coordination compounds of various structures, see: Saalfrank et al. (2001); Yilmaz et al. (2000).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms and uncoordinated H₂O molecular.

[N-(8-Quinolylmethyl)iminodiethanol-κ⁴N,N',O,O']bis(thiocyanato- κN)nickel(II) monohydrate top

Crystal data top

[Ni(NCS)₂(C₁₄H₁₈N₂O₂)]·H₂O	F(000) = 912
M_r = 439.19	D_x = 1.553 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.693 (6) Å	Cell parameters from 783 reflections
b = 10.142 (4) Å	θ = 2.6–25.0°
c = 13.965 (6) Å	µ = 1.28 mm⁻¹
β = 115.460 (6)°	T = 293 K
V = 1878.9 (13) Å³	Block, green
Z = 4	0.15 × 0.10 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3783 independent reflections
Radiation source: fine-focus sealed tube	2673 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 26.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −18→13
T_min = 0.800, T_max = 1.000	k = −11→12
8517 measured reflections	l = −6→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0367P)² + 0.8315P] where P = (F_o² + 2F_c²)/3
3783 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Ni(NCS)₂(C₁₄H₁₈N₂O₂)]·H₂O	V = 1878.9 (13) Å³
M_r = 439.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.693 (6) Å	µ = 1.28 mm⁻¹
b = 10.142 (4) Å	T = 293 K
c = 13.965 (6) Å	0.15 × 0.10 × 0.08 mm
β = 115.460 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3783 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2673 reflections with I > 2σ(I)
T_min = 0.800, T_max = 1.000	R_int = 0.033
8517 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.08	Δρ_max = 0.50 e Å⁻³
3783 reflections	Δρ_min = −0.40 e Å⁻³
235 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	0.20147 (3)	0.81623 (4)	0.28870 (3)	0.03578 (13)
O1	0.15578 (17)	0.7221 (2)	0.39381 (17)	0.0461 (6)
H1A	0.1344	0.6349	0.3868	0.055*
O2	0.05232 (18)	0.8491 (2)	0.1858 (2)	0.0596 (7)
H2A	0.0136	0.7863	0.1366	0.072*
O3	0.9140 (3)	0.7780 (4)	1.0013 (3)	0.1413 (18)
H31	0.9448	0.8434	0.9906	0.212*
H32	0.8905	0.7275	0.9473	0.212*
N1	0.35206 (19)	0.8079 (3)	0.4011 (2)	0.0399 (6)
N2	0.1710 (2)	0.9792 (2)	0.3581 (2)	0.0391 (6)
N3	0.2430 (2)	0.9143 (3)	0.1887 (2)	0.0513 (8)
N4	0.1975 (2)	0.6352 (3)	0.2271 (2)	0.0500 (7)
S1	0.27361 (8)	1.03083 (10)	0.02603 (8)	0.0606 (3)
S2	0.20208 (9)	0.36476 (10)	0.22047 (9)	0.0679 (3)
C1	0.4045 (3)	0.7104 (4)	0.3897 (3)	0.0561 (10)
H1	0.3790	0.6661	0.3251	0.067*
C2	0.4961 (3)	0.6688 (4)	0.4681 (4)	0.0707 (12)
H2	0.5323	0.6018	0.4549	0.085*
C3	0.5309 (3)	0.7265 (4)	0.5624 (4)	0.0699 (13)
H3	0.5896	0.6954	0.6175	0.084*
C4	0.4804 (3)	0.8329 (4)	0.5791 (3)	0.0558 (10)
C5	0.5166 (3)	0.9007 (5)	0.6756 (3)	0.0753 (13)
H5	0.5740	0.8707	0.7330	0.090*
C6	0.4696 (4)	1.0072 (6)	0.6857 (3)	0.0832 (15)
H6	0.4936	1.0506	0.7507	0.100*
C7	0.3841 (3)	1.0554 (4)	0.6000 (3)	0.0627 (11)
H7	0.3535	1.1319	0.6086	0.075*
C8	0.3448 (3)	0.9931 (3)	0.5044 (3)	0.0453 (8)
C9	0.3920 (2)	0.8769 (3)	0.4943 (3)	0.0418 (8)
C10	0.2622 (3)	1.0574 (3)	0.4120 (3)	0.0457 (8)
H10A	0.2442	1.1388	0.4361	0.055*
H10B	0.2879	1.0807	0.3609	0.055*
C11	0.1257 (3)	0.9385 (3)	0.4299 (3)	0.0528 (9)
H11A	0.0529	0.9372	0.3907	0.063*
H11B	0.1429	1.0026	0.4866	0.063*
C12	0.1611 (3)	0.8060 (4)	0.4765 (3)	0.0543 (9)
H12A	0.2299	0.8110	0.5309	0.065*
H12B	0.1187	0.7724	0.5085	0.065*
C13	0.0982 (3)	1.0567 (3)	0.2689 (3)	0.0522 (9)
H13A	0.1325	1.0963	0.2302	0.063*
H13B	0.0715	1.1272	0.2962	0.063*
C14	0.0131 (3)	0.9727 (4)	0.1949 (3)	0.0636 (11)
H14A	−0.0369	0.9617	0.2224	0.076*
H14B	−0.0191	1.0145	0.1259	0.076*
C15	0.2565 (2)	0.9625 (3)	0.1223 (3)	0.0412 (8)
C16	0.1984 (2)	0.5241 (4)	0.2227 (2)	0.0410 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0407 (2)	0.0316 (2)	0.0351 (2)	0.00054 (19)	0.01630 (17)	0.00133 (19)
O1	0.0596 (15)	0.0355 (12)	0.0487 (13)	−0.0080 (11)	0.0285 (12)	−0.0020 (11)
O2	0.0500 (15)	0.0436 (15)	0.0632 (16)	0.0030 (12)	0.0033 (13)	−0.0080 (13)
O3	0.129 (3)	0.119 (3)	0.089 (3)	0.042 (3)	−0.034 (2)	−0.044 (2)
N1	0.0388 (15)	0.0357 (15)	0.0473 (15)	0.0007 (13)	0.0204 (13)	0.0018 (13)
N2	0.0401 (15)	0.0323 (14)	0.0452 (15)	0.0015 (12)	0.0185 (13)	0.0009 (12)
N3	0.066 (2)	0.0496 (18)	0.0418 (16)	−0.0036 (15)	0.0270 (16)	0.0034 (15)
N4	0.068 (2)	0.0354 (16)	0.0477 (17)	0.0002 (15)	0.0261 (16)	−0.0028 (14)
S1	0.0704 (7)	0.0682 (7)	0.0519 (6)	−0.0214 (5)	0.0346 (5)	0.0013 (5)
S2	0.0805 (8)	0.0359 (5)	0.0753 (7)	−0.0001 (5)	0.0221 (6)	−0.0013 (5)
C1	0.043 (2)	0.051 (2)	0.077 (3)	0.0035 (18)	0.028 (2)	−0.002 (2)
C2	0.041 (2)	0.053 (3)	0.116 (4)	0.0086 (19)	0.031 (3)	0.011 (3)
C3	0.034 (2)	0.066 (3)	0.093 (3)	0.000 (2)	0.012 (2)	0.028 (3)
C4	0.037 (2)	0.064 (3)	0.059 (2)	−0.0102 (19)	0.0132 (18)	0.011 (2)
C5	0.052 (3)	0.100 (4)	0.052 (3)	−0.017 (3)	0.001 (2)	0.013 (3)
C6	0.074 (3)	0.116 (4)	0.047 (3)	−0.037 (3)	0.015 (2)	−0.020 (3)
C7	0.064 (3)	0.065 (3)	0.059 (2)	−0.015 (2)	0.026 (2)	−0.018 (2)
C8	0.044 (2)	0.047 (2)	0.046 (2)	−0.0124 (17)	0.0198 (16)	−0.0067 (17)
C9	0.0385 (19)	0.0432 (19)	0.0433 (19)	−0.0064 (16)	0.0173 (16)	0.0044 (16)
C10	0.051 (2)	0.0290 (17)	0.057 (2)	−0.0036 (16)	0.0235 (18)	−0.0068 (16)
C11	0.059 (2)	0.050 (2)	0.061 (2)	0.0010 (18)	0.036 (2)	−0.0048 (19)
C12	0.072 (3)	0.051 (2)	0.054 (2)	0.000 (2)	0.039 (2)	0.0027 (19)
C13	0.053 (2)	0.0356 (19)	0.063 (2)	0.0103 (17)	0.0205 (19)	0.0040 (18)
C14	0.052 (2)	0.058 (3)	0.067 (3)	0.013 (2)	0.012 (2)	0.003 (2)
C15	0.0418 (19)	0.0401 (19)	0.0387 (18)	−0.0025 (15)	0.0143 (15)	−0.0036 (15)
C16	0.043 (2)	0.048 (2)	0.0321 (17)	−0.0027 (16)	0.0161 (15)	−0.0015 (16)

Geometric parameters (Å, º) top

Ni1—N3	2.011 (3)	C3—C4	1.385 (6)
Ni1—N4	2.018 (3)	C3—H3	0.9300
Ni1—N2	2.061 (3)	C4—C5	1.398 (6)
Ni1—O2	2.067 (2)	C4—C9	1.403 (5)
Ni1—O1	2.089 (2)	C5—C6	1.322 (7)
Ni1—N1	2.093 (3)	C5—H5	0.9300
O1—C12	1.409 (4)	C6—C7	1.399 (6)
O1—H1A	0.9300	C6—H6	0.9300
O2—C14	1.408 (4)	C7—C8	1.362 (5)
O2—H2A	0.9300	C7—H7	0.9300
O3—H31	0.8520	C8—C9	1.406 (5)
O3—H32	0.8520	C8—C10	1.488 (5)
N1—C1	1.305 (4)	C10—H10A	0.9700
N1—C9	1.368 (4)	C10—H10B	0.9700
N2—C10	1.457 (4)	C11—C12	1.486 (5)
N2—C13	1.472 (4)	C11—H11A	0.9700
N2—C11	1.481 (4)	C11—H11B	0.9700
N3—C15	1.139 (4)	C12—H12A	0.9700
N4—C16	1.129 (4)	C12—H12B	0.9700
S1—C15	1.625 (3)	C13—C14	1.499 (5)
S2—C16	1.617 (4)	C13—H13A	0.9700
C1—C2	1.385 (6)	C13—H13B	0.9700
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.326 (6)	C14—H14B	0.9700
C2—H2	0.9300

N3—Ni1—N4	96.64 (12)	C6—C5—H5	119.8
N3—Ni1—N2	97.00 (11)	C4—C5—H5	119.8
N4—Ni1—N2	163.40 (11)	C5—C6—C7	120.8 (4)
N3—Ni1—O2	89.15 (12)	C5—C6—H6	119.6
N4—Ni1—O2	91.29 (11)	C7—C6—H6	119.6
N2—Ni1—O2	79.51 (10)	C8—C7—C6	121.6 (4)
N3—Ni1—O1	177.48 (10)	C8—C7—H7	119.2
N4—Ni1—O1	85.70 (10)	C6—C7—H7	119.2
N2—Ni1—O1	80.54 (10)	C7—C8—C9	117.9 (4)
O2—Ni1—O1	89.84 (10)	C7—C8—C10	119.4 (3)
N3—Ni1—N1	90.10 (12)	C9—C8—C10	122.3 (3)
N4—Ni1—N1	96.35 (11)	N1—C9—C4	120.3 (3)
N2—Ni1—N1	93.04 (10)	N1—C9—C8	119.7 (3)
O2—Ni1—N1	172.36 (10)	C4—C9—C8	120.0 (3)
O1—Ni1—N1	90.59 (10)	N2—C10—C8	115.8 (3)
C12—O1—Ni1	112.29 (19)	N2—C10—H10A	108.3
C12—O1—H1A	123.9	C8—C10—H10A	108.3
Ni1—O1—H1A	123.9	N2—C10—H10B	108.3
C14—O2—Ni1	115.7 (2)	C8—C10—H10B	108.3
C14—O2—H2A	122.1	H10A—C10—H10B	107.4
Ni1—O2—H2A	122.1	N2—C11—C12	112.0 (3)
H31—O3—H32	110.9	N2—C11—H11A	109.2
C1—N1—C9	118.0 (3)	C12—C11—H11A	109.2
C1—N1—Ni1	115.4 (2)	N2—C11—H11B	109.2
C9—N1—Ni1	125.2 (2)	C12—C11—H11B	109.2
C10—N2—C13	108.6 (3)	H11A—C11—H11B	107.9
C10—N2—C11	112.5 (3)	O1—C12—C11	107.5 (3)
C13—N2—C11	110.3 (3)	O1—C12—H12A	110.2
C10—N2—Ni1	110.02 (19)	C11—C12—H12A	110.2
C13—N2—Ni1	104.8 (2)	O1—C12—H12B	110.2
C11—N2—Ni1	110.26 (19)	C11—C12—H12B	110.2
C15—N3—Ni1	171.5 (3)	H12A—C12—H12B	108.5
C16—N4—Ni1	158.8 (3)	N2—C13—C14	111.6 (3)
N1—C1—C2	123.9 (4)	N2—C13—H13A	109.3
N1—C1—H1	118.0	C14—C13—H13A	109.3
C2—C1—H1	118.0	N2—C13—H13B	109.3
C3—C2—C1	118.7 (4)	C14—C13—H13B	109.3
C3—C2—H2	120.7	H13A—C13—H13B	108.0
C1—C2—H2	120.7	O2—C14—C13	108.4 (3)
C2—C3—C4	120.3 (4)	O2—C14—H14A	110.0
C2—C3—H3	119.8	C13—C14—H14A	110.0
C4—C3—H3	119.8	O2—C14—H14B	110.0
C3—C4—C5	122.5 (4)	C13—C14—H14B	110.0
C3—C4—C9	118.3 (4)	H14A—C14—H14B	108.4
C5—C4—C9	119.2 (4)	N3—C15—S1	178.9 (3)
C6—C5—C4	120.3 (4)	N4—C16—S2	178.2 (4)

N3—Ni1—O1—C12	−32 (3)	O1—Ni1—N4—C16	−22.4 (8)
N4—Ni1—O1—C12	169.9 (2)	N1—Ni1—N4—C16	67.7 (8)
N2—Ni1—O1—C12	−19.4 (2)	C9—N1—C1—C2	3.0 (5)
O2—Ni1—O1—C12	−98.8 (2)	Ni1—N1—C1—C2	−163.8 (3)
N1—Ni1—O1—C12	73.5 (2)	N1—C1—C2—C3	3.4 (6)
N3—Ni1—O2—C14	−82.8 (3)	C1—C2—C3—C4	−4.9 (6)
N4—Ni1—O2—C14	−179.4 (3)	C2—C3—C4—C5	−177.1 (4)
N2—Ni1—O2—C14	14.5 (3)	C2—C3—C4—C9	0.2 (6)
O1—Ni1—O2—C14	94.9 (3)	C3—C4—C5—C6	175.3 (4)
N1—Ni1—O2—C14	1.6 (9)	C9—C4—C5—C6	−1.9 (6)
N3—Ni1—N1—C1	−84.8 (3)	C4—C5—C6—C7	−1.1 (7)
N4—Ni1—N1—C1	11.9 (3)	C5—C6—C7—C8	1.7 (7)
N2—Ni1—N1—C1	178.2 (3)	C6—C7—C8—C9	0.8 (6)
O2—Ni1—N1—C1	−169.2 (7)	C6—C7—C8—C10	−172.1 (4)
O1—Ni1—N1—C1	97.6 (3)	C1—N1—C9—C4	−7.9 (5)
N3—Ni1—N1—C9	109.5 (3)	Ni1—N1—C9—C4	157.5 (2)
N4—Ni1—N1—C9	−153.9 (2)	C1—N1—C9—C8	171.4 (3)
N2—Ni1—N1—C9	12.4 (3)	Ni1—N1—C9—C8	−23.2 (4)
O2—Ni1—N1—C9	25.1 (9)	C3—C4—C9—N1	6.4 (5)
O1—Ni1—N1—C9	−68.1 (2)	C5—C4—C9—N1	−176.3 (3)
N3—Ni1—N2—C10	−62.0 (2)	C3—C4—C9—C8	−172.9 (3)
N4—Ni1—N2—C10	153.0 (4)	C5—C4—C9—C8	4.4 (5)
O2—Ni1—N2—C10	−149.8 (2)	C7—C8—C9—N1	176.9 (3)
O1—Ni1—N2—C10	118.6 (2)	C10—C8—C9—N1	−10.4 (5)
N1—Ni1—N2—C10	28.5 (2)	C7—C8—C9—C4	−3.8 (5)
N3—Ni1—N2—C13	54.6 (2)	C10—C8—C9—C4	168.9 (3)
N4—Ni1—N2—C13	−90.4 (4)	C13—N2—C10—C8	−179.4 (3)
O2—Ni1—N2—C13	−33.2 (2)	C11—N2—C10—C8	58.1 (4)
O1—Ni1—N2—C13	−124.8 (2)	Ni1—N2—C10—C8	−65.3 (3)
N1—Ni1—N2—C13	145.1 (2)	C7—C8—C10—N2	−125.4 (3)
N3—Ni1—N2—C11	173.3 (2)	C9—C8—C10—N2	62.1 (4)
N4—Ni1—N2—C11	28.3 (5)	C10—N2—C11—C12	−93.4 (3)
O2—Ni1—N2—C11	85.5 (2)	C13—N2—C11—C12	145.1 (3)
O1—Ni1—N2—C11	−6.1 (2)	Ni1—N2—C11—C12	29.8 (4)
N1—Ni1—N2—C11	−96.2 (2)	Ni1—O1—C12—C11	39.9 (3)
N4—Ni1—N3—C15	53 (2)	N2—C11—C12—O1	−45.8 (4)
N2—Ni1—N3—C15	−117 (2)	C10—N2—C13—C14	166.7 (3)
O2—Ni1—N3—C15	−38 (2)	C11—N2—C13—C14	−69.5 (4)
O1—Ni1—N3—C15	−104 (3)	Ni1—N2—C13—C14	49.1 (3)
N1—Ni1—N3—C15	150 (2)	Ni1—O2—C14—C13	8.5 (4)
N3—Ni1—N4—C16	158.5 (8)	N2—C13—C14—O2	−38.5 (4)
N2—Ni1—N4—C16	−56.4 (10)	Ni1—N3—C15—S1	20 (20)
O2—Ni1—N4—C16	−112.2 (8)	Ni1—N4—C16—S2	−31 (11)

Experimental details

Crystal data
Chemical formula	[Ni(NCS)₂(C₁₄H₁₈N₂O₂)]·H₂O
M_r	439.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.693 (6), 10.142 (4), 13.965 (6)
β (°)	115.460 (6)
V (Å³)	1878.9 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.15 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.800, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8517, 3783, 2673
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.097, 1.08
No. of reflections	3783
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.40

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).

Selected geometric parameters (Å, º) top

Ni1—N3	2.011 (3)	Ni1—O2	2.067 (2)
Ni1—N4	2.018 (3)	Ni1—O1	2.089 (2)
Ni1—N2	2.061 (3)	Ni1—N1	2.093 (3)

N3—Ni1—N4	96.64 (12)	N2—Ni1—O1	80.54 (10)
N3—Ni1—N2	97.00 (11)	O2—Ni1—O1	89.84 (10)
N3—Ni1—O2	89.15 (12)	N3—Ni1—N1	90.10 (12)
N4—Ni1—O2	91.29 (11)	N4—Ni1—N1	96.35 (11)
N2—Ni1—O2	79.51 (10)	N2—Ni1—N1	93.04 (10)
N4—Ni1—O1	85.70 (10)	O1—Ni1—N1	90.59 (10)

Acknowledgements

This work was supported by the Qinglan Project Foundation of the University of Jiangsu Province and the Science Foundation of the University of Science and Technology of Suzhou.

References

Bruker (1998). SHELXTL and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany. Google Scholar
Yilmaz, V. T., Karadag, A., Thöne, C. & Herbst-Irmer, R. (2000). Acta Cryst. C56, 948–949. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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