Aqua­{N,N-dimethyl-N′-[1-(2-pyrid­yl)ethyl­idene]ethane-1,2-diamine-κ3N,N′,N′′}bis­(thio­cyanato-κN)nickel(II)

Suleiman Gwaram, N.; Saharin, S.M.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811011512

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m513

doi:10.1107/S1600536811011512

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Aqua{N,N-dimethyl-N′-[1-(2-pyridyl)ethylidene]ethane-1,2-diamine-κ³N,N′,N′′}bis(thiocyanato-κN)nickel(II)

Nura Suleiman Gwaram,^a Siti Munirah Saharin,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 24 March 2011; accepted 28 March 2011; online 31 March 2011)

In the title compound, [Ni(NCS)₂(C₁₁H₁₇N₃)(H₂O)], the Ni^II ion is six-coordinated by the N,N′,N"-tridentate Schiff base N atoms, two cis-positioned N-bound isothiocyanate groups and one water molecule. In the crystal, O—H⋯S hydrogen bonds link adjacent molecules into infinite layers parallel to the ac plane. The layers are further connected into a three-dimensional network via C—H⋯π interactions. The –CH₂–N(CH₃)₂ fragment is disordered over two sets of sites in a 0.556 (5):0.444 (5) ratio.

Related literature

For the structure of a similar mononuclear nickel(II) thiocyanate complex, see: Suleiman Gwaram et al. (2011 ). For dimeric nickel(II) thiocyanate complexes with similar Schiff bases, see: Diao (2007 ); Bhowmik et al. (2010 ).

Experimental

Crystal data

[Ni(NCS)₂(C₁₁H₁₇N₃)(H₂O)]
M_r = 384.16
Monoclinic, C c
a = 12.8404 (2) Å
b = 14.2623 (3) Å
c = 9.5868 (2) Å
β = 99.467 (1)°
V = 1731.75 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.37 mm⁻¹
T = 100 K
0.22 × 0.19 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.753, T_max = 0.864
7792 measured reflections
3698 independent reflections
3451 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.070
S = 1.02
3698 reflections
234 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.52 e Å⁻³
Absolute structure: Flack (1983 ), 1798 Friedel pairs
Flack parameter: 0.020 (11)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C1–C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯S1ⁱ	0.82 (2)	2.38 (2)	3.181 (3)	164 (4)
O1—H1A⋯S2ⁱⁱ	0.84 (2)	2.35 (2)	3.190 (3)	178 (4)
C7—H7C⋯Cg1ⁱⁱⁱ	0.98	2.88	3.531 (3)	125
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011512/go2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011512/go2008Isup2.hkl

checkCIF report

Comment top

The title mixed-ligand complex was obtained via the treatment of nickel(II) ion with the Schiff base N,N-dimethyl-N'-[methyl(2-pyridyl)methylene]ethane-1,2-diamine, prepared in situ, and the thiocyanate salt. The Schiff base acts as an N,N',N"-tridentate chelate and the two thiocyanate ions behave in an N-donor fashion towards the Ni^II ion. The geometry around the metal center is completed by one water O atom. This arrangement is similar to what was observed in the nickel(II) thiocyanate complex of a similar Schiff base (Suleiman Gwaram et al., 2011). In contrast, the metal ions in the nickel(II) thiocyanate complex of N,N-dimethyl-N'-(2-pyridylmethylene)ethane-1,2-diamine (Diao, 2007) and N,N-diethyl-N'-[methyl(2-pyridyl)methylene]ethane-1,2-diamine (Bhowmik et al., 2010) are doubly bridged into dimers by N:S-bridging thiocyanate ligands. In the present structure, the adjacent molecules are connected into 2-D arrays in ac plane via O—H···S interactions (Table 1, Fig. 2). A C—H···π interaction (Table 1) connects the layers into a three-dimensional structure.

Related literature top

For the structure of a similar mononuclear nickel(II) thiocyanate complex, see: Suleiman Gwaram et al. (2011). For dimeric nickel(II) thiocyanate complexes with similar Schiff bases, see: Diao (2007); Bhowmik et al. (2010).

Experimental top

A mixture of 2-acetylpyridine (0.2 g, 1.65 mmol) and N,N-dimethylethyldiamine (0.15 g, 1.65 mmol) in ethanol (20 ml) was refluxed for 2 h followed by addition of a solution of nickel(II) acetate tetrahydrate (0.41 g, 1.65 mmol) and sodium thiocyanate (0.27 g, 3.3 mmol) in a minimum amount of water. The resulting solution was refluxed for 30 min, then set aside at room temperature. Brown crystals of the title compound were obtained by slow evaporation of the resulting reaction mixture.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Only the major disordered component is shown.
	Fig. 2. Unit-cell packing of the title compound, viewed down the b axis, showing the O—H···S hydrogen-bonded two-dimensional network. C-bound hydrogen atoms have been omitted for clarity.

Aqua{N,N-dimethyl-N'-[1-(2-pyridyl)ethylidene]ethane-1,2-diamine-κ³N,N',N''}bis(thiocyanato-κN)nickel(II) top

Crystal data top

[Ni(NCS)₂(C₁₁H₁₇N₃)(H₂O)]	F(000) = 800
M_r = 384.16	D_x = 1.473 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2239 reflections
a = 12.8404 (2) Å	θ = 2.9–27.9°
b = 14.2623 (3) Å	µ = 1.37 mm⁻¹
c = 9.5868 (2) Å	T = 100 K
β = 99.467 (1)°	Block, brown
V = 1731.75 (6) Å³	0.22 × 0.19 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3698 independent reflections
Radiation source: fine-focus sealed tube	3451 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.753, T_max = 0.864	k = −18→18
7792 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0313P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3698 reflections	Δρ_max = 0.58 e Å⁻³
234 parameters	Δρ_min = −0.52 e Å⁻³
16 restraints	Absolute structure: Flack (1983), 1798 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.020 (11)

Crystal data top

[Ni(NCS)₂(C₁₁H₁₇N₃)(H₂O)]	V = 1731.75 (6) Å³
M_r = 384.16	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 12.8404 (2) Å	µ = 1.37 mm⁻¹
b = 14.2623 (3) Å	T = 100 K
c = 9.5868 (2) Å	0.22 × 0.19 × 0.11 mm
β = 99.467 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3698 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3451 reflections with I > 2σ(I)
T_min = 0.753, T_max = 0.864	R_int = 0.026
7792 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.070	Δρ_max = 0.58 e Å⁻³
S = 1.02	Δρ_min = −0.52 e Å⁻³
3698 reflections	Absolute structure: Flack (1983), 1798 Friedel pairs
234 parameters	Absolute structure parameter: 0.020 (11)
16 restraints

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	Occ. (<1)
Ni1	0.53275 (7)	0.77376 (2)	0.26546 (8)	0.01875 (9)
S1	0.66956 (9)	0.64265 (6)	0.72084 (11)	0.02834 (19)
S2	0.87020 (9)	0.82690 (6)	0.13658 (11)	0.02889 (19)
O1	0.3999 (2)	0.79724 (19)	0.3691 (3)	0.0272 (5)
H1A	0.392 (3)	0.763 (2)	0.438 (3)	0.041*
H1B	0.3417 (19)	0.804 (3)	0.319 (3)	0.041*
N1	0.55528 (19)	0.91914 (17)	0.2861 (3)	0.0203 (6)
N2	0.4415 (2)	0.82344 (18)	0.0894 (2)	0.0212 (5)
N3	0.47431 (16)	0.64117 (17)	0.1766 (2)	0.0310 (6)
N4	0.6034 (2)	0.72811 (19)	0.4589 (3)	0.0292 (6)
N5	0.6702 (3)	0.7681 (2)	0.1831 (3)	0.0278 (7)
C1	0.6229 (3)	0.9645 (2)	0.3838 (3)	0.0286 (7)
H1	0.6663	0.9295	0.4551	0.034*
C2	0.6315 (3)	1.0619 (3)	0.3840 (4)	0.0433 (10)
H2	0.6805	1.0929	0.4540	0.052*
C3	0.5683 (3)	1.1122 (3)	0.2819 (4)	0.0421 (10)
H3	0.5722	1.1788	0.2816	0.050*
C4	0.4990 (3)	1.0663 (2)	0.1793 (4)	0.0360 (8)
H4	0.4552	1.1004	0.1070	0.043*
C5	0.4946 (2)	0.9689 (2)	0.1842 (3)	0.0223 (6)
C6	0.4261 (2)	0.9115 (2)	0.0758 (3)	0.0242 (6)
C7	0.3465 (3)	0.9581 (3)	−0.0336 (3)	0.0360 (8)
H7A	0.2898	0.9845	0.0114	0.054*
H7B	0.3168	0.9119	−0.1049	0.054*
H7C	0.3806	1.0084	−0.0791	0.054*
C8	0.3855 (3)	0.7537 (2)	−0.0046 (3)	0.0297 (7)
H8A	0.3824	0.7729	−0.1044	0.036*
H8B	0.3125	0.7462	0.0144	0.036*
C9	0.4462 (4)	0.6625 (3)	0.0238 (2)	0.0265 (14)	0.556 (5)
H9A	0.4029	0.6106	−0.0234	0.032*	0.556 (5)
H9B	0.5116	0.6663	−0.0179	0.032*	0.556 (5)
C10	0.5496 (4)	0.5631 (3)	0.2016 (7)	0.0375 (17)	0.556 (5)
H10A	0.5166	0.5060	0.1578	0.056*	0.556 (5)
H10B	0.5700	0.5532	0.3035	0.056*	0.556 (5)
H10C	0.6124	0.5780	0.1600	0.056*	0.556 (5)
C11	0.3747 (3)	0.6125 (4)	0.2213 (6)	0.0306 (15)	0.556 (5)
H11A	0.3520	0.5521	0.1780	0.046*	0.556 (5)
H11B	0.3203	0.6599	0.1912	0.046*	0.556 (5)
H11C	0.3854	0.6065	0.3245	0.046*	0.556 (5)
C9'	0.3761 (3)	0.6644 (4)	0.0790 (7)	0.045 (2)	0.444 (5)
H9'A	0.3179	0.6716	0.1342	0.053*	0.444 (5)
H9'B	0.3579	0.6117	0.0122	0.053*	0.444 (5)
C10'	0.5540 (5)	0.5991 (6)	0.1017 (9)	0.045 (2)	0.444 (5)
H10D	0.5281	0.5388	0.0610	0.067*	0.444 (5)
H10E	0.6197	0.5893	0.1682	0.067*	0.444 (5)
H10F	0.5675	0.6412	0.0259	0.067*	0.444 (5)
C11'	0.4673 (8)	0.5708 (4)	0.2867 (6)	0.039 (2)	0.444 (5)
H11D	0.4406	0.5117	0.2424	0.059*	0.444 (5)
H11E	0.4191	0.5932	0.3489	0.059*	0.444 (5)
H11F	0.5375	0.5606	0.3425	0.059*	0.444 (5)
C12	0.6312 (3)	0.6935 (2)	0.5665 (3)	0.0236 (6)
C13	0.7532 (3)	0.7906 (2)	0.1624 (3)	0.0244 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02124 (18)	0.01989 (18)	0.01472 (16)	−0.00167 (17)	0.00176 (13)	0.00004 (16)
S1	0.0305 (5)	0.0303 (4)	0.0227 (4)	0.0010 (3)	−0.0001 (3)	0.0074 (3)
S2	0.0281 (4)	0.0372 (5)	0.0227 (4)	0.0023 (3)	0.0082 (3)	0.0004 (3)
O1	0.0213 (13)	0.0379 (14)	0.0219 (12)	−0.0058 (10)	0.0023 (10)	0.0021 (10)
N1	0.0196 (15)	0.0235 (13)	0.0185 (13)	−0.0052 (10)	0.0055 (11)	−0.0028 (10)
N2	0.0195 (13)	0.0293 (15)	0.0150 (12)	−0.0046 (11)	0.0030 (10)	−0.0051 (10)
N3	0.0463 (18)	0.0230 (15)	0.0254 (13)	−0.0079 (12)	0.0112 (13)	−0.0063 (11)
N4	0.0311 (16)	0.0345 (17)	0.0222 (14)	0.0040 (12)	0.0044 (12)	0.0035 (12)
N5	0.0287 (17)	0.0344 (17)	0.0215 (14)	0.0071 (13)	0.0075 (13)	0.0040 (11)
C1	0.0273 (18)	0.037 (2)	0.0227 (16)	−0.0095 (15)	0.0072 (14)	−0.0096 (14)
C2	0.049 (2)	0.046 (2)	0.039 (2)	−0.0252 (19)	0.0200 (19)	−0.0243 (18)
C3	0.063 (3)	0.0250 (18)	0.045 (2)	−0.0114 (16)	0.027 (2)	−0.0077 (16)
C4	0.052 (2)	0.0250 (19)	0.0353 (18)	0.0013 (16)	0.0211 (18)	0.0043 (14)
C5	0.0256 (17)	0.0223 (16)	0.0217 (14)	0.0011 (13)	0.0117 (13)	0.0036 (12)
C6	0.0230 (16)	0.0302 (18)	0.0206 (15)	0.0014 (13)	0.0073 (12)	0.0066 (13)
C7	0.0299 (18)	0.051 (2)	0.0275 (18)	0.0088 (16)	0.0050 (15)	0.0158 (16)
C8	0.0271 (17)	0.042 (2)	0.0194 (15)	−0.0122 (15)	0.0010 (13)	−0.0066 (13)
C9	0.023 (3)	0.027 (3)	0.029 (3)	−0.004 (2)	0.001 (3)	−0.012 (2)
C10	0.050 (4)	0.027 (4)	0.037 (4)	0.001 (3)	0.013 (3)	0.002 (3)
C11	0.035 (3)	0.023 (3)	0.034 (3)	−0.005 (2)	0.007 (3)	−0.005 (2)
C9'	0.035 (5)	0.050 (6)	0.050 (5)	−0.018 (4)	0.012 (4)	−0.021 (4)
C10'	0.039 (5)	0.025 (5)	0.065 (6)	0.000 (4)	−0.008 (5)	−0.007 (4)
C11'	0.063 (6)	0.017 (4)	0.039 (5)	0.001 (4)	0.013 (4)	−0.003 (3)
C12	0.0241 (16)	0.0217 (16)	0.0249 (16)	0.0005 (13)	0.0037 (13)	−0.0018 (13)
C13	0.0317 (18)	0.0262 (17)	0.0160 (14)	0.0121 (14)	0.0060 (13)	0.0054 (12)

Geometric parameters (Å, º) top

Ni1—N2	2.018 (2)	C4—C5	1.392 (4)
Ni1—N4	2.033 (3)	C4—H4	0.9500
Ni1—N5	2.050 (3)	C5—C6	1.491 (4)
Ni1—N1	2.098 (2)	C6—C7	1.495 (4)
Ni1—O1	2.137 (2)	C7—H7A	0.9800
Ni1—N3	2.158 (2)	C7—H7B	0.9800
S1—C12	1.648 (3)	C7—H7C	0.9800
S2—C13	1.645 (4)	C8—C9	1.5180 (10)
O1—H1A	0.836 (18)	C8—C9'	1.5204 (10)
O1—H1B	0.824 (19)	C8—H8A	0.9900
N1—C1	1.335 (4)	C8—H8B	0.9900
N1—C5	1.347 (4)	C9—H9A	0.9900
N2—C6	1.275 (4)	C9—H9B	0.9900
N2—C8	1.451 (4)	C10—H10A	0.9800
N3—C10	1.4683 (10)	C10—H10B	0.9800
N3—C11'	1.4706 (10)	C10—H10C	0.9800
N3—C10'	1.4716 (10)	C11—H11A	0.9800
N3—C11	1.4725 (10)	C11—H11B	0.9800
N3—C9'	1.4783 (10)	C11—H11C	0.9800
N3—C9	1.4810 (10)	C9'—H9'A	0.9900
N4—C12	1.147 (4)	C9'—H9'B	0.9900
N5—C13	1.162 (4)	C10'—H10D	0.9800
C1—C2	1.394 (5)	C10'—H10E	0.9800
C1—H1	0.9500	C10'—H10F	0.9800
C2—C3	1.368 (5)	C11'—H11D	0.9800
C2—H2	0.9500	C11'—H11E	0.9800
C3—C4	1.378 (5)	C11'—H11F	0.9800
C3—H3	0.9500

N2—Ni1—N4	170.38 (10)	N1—C5—C6	114.9 (3)
N2—Ni1—N5	96.32 (11)	C4—C5—C6	123.1 (3)
N4—Ni1—N5	93.17 (11)	N2—C6—C5	113.9 (3)
N2—Ni1—N1	77.53 (9)	N2—C6—C7	125.9 (3)
N4—Ni1—N1	101.33 (10)	C5—C6—C7	120.2 (3)
N5—Ni1—N1	87.79 (10)	C6—C7—H7A	109.5
N2—Ni1—O1	86.32 (9)	C6—C7—H7B	109.5
N4—Ni1—O1	84.06 (10)	H7A—C7—H7B	109.5
N5—Ni1—O1	171.42 (11)	C6—C7—H7C	109.5
N1—Ni1—O1	84.80 (10)	H7A—C7—H7C	109.5
N2—Ni1—N3	82.01 (10)	H7B—C7—H7C	109.5
N4—Ni1—N3	98.83 (10)	N2—C8—C9	106.8 (3)
N5—Ni1—N3	94.52 (11)	N2—C8—C9'	108.7 (3)
N1—Ni1—N3	159.55 (9)	N2—C8—H8A	110.4
O1—Ni1—N3	93.93 (10)	C9—C8—H8A	110.4
Ni1—O1—H1A	119 (3)	C9'—C8—H8A	138.3
Ni1—O1—H1B	118 (3)	N2—C8—H8B	110.4
H1A—O1—H1B	108 (4)	C9—C8—H8B	110.4
C1—N1—C5	119.0 (3)	C9'—C8—H8B	69.7
C1—N1—Ni1	127.5 (2)	H8A—C8—H8B	108.6
C5—N1—Ni1	113.44 (19)	N3—C9—C8	112.8 (3)
C6—N2—C8	124.0 (3)	N3—C9—H9A	109.0
C6—N2—Ni1	119.4 (2)	C8—C9—H9A	109.0
C8—N2—Ni1	116.04 (19)	N3—C9—H9B	109.0
C10—N3—C11'	58.8 (4)	C8—C9—H9B	109.0
C11'—N3—C10'	101.7 (5)	H9A—C9—H9B	107.8
C10—N3—C11	108.8 (4)	N3—C10—H10A	109.5
C11'—N3—C11	56.1 (4)	N3—C10—H10B	109.5
C10'—N3—C11	137.4 (4)	H10A—C10—H10B	109.5
C10—N3—C9'	138.0 (4)	N3—C10—H10C	109.5
C11'—N3—C9'	117.4 (4)	H10A—C10—H10C	109.5
C10'—N3—C9'	111.8 (5)	H10B—C10—H10C	109.5
C11—N3—C9'	63.6 (3)	N3—C11—H11A	109.5
C10—N3—C9	111.3 (3)	N3—C11—H11B	109.5
C11'—N3—C9	144.7 (4)	H11A—C11—H11B	109.5
C10'—N3—C9	71.2 (4)	N3—C11—H11C	109.5
C11—N3—C9	105.2 (4)	H11A—C11—H11C	109.5
C10—N3—Ni1	115.1 (3)	H11B—C11—H11C	109.5
C11'—N3—Ni1	111.9 (3)	N3—C9'—C8	112.8 (3)
C10'—N3—Ni1	109.0 (3)	N3—C9'—H9'A	109.0
C11—N3—Ni1	113.0 (3)	C8—C9'—H9'A	109.0
C9'—N3—Ni1	105.0 (3)	N3—C9'—H9'B	109.0
C9—N3—Ni1	102.9 (2)	C8—C9'—H9'B	109.0
C12—N4—Ni1	170.1 (3)	H9'A—C9'—H9'B	107.8
C13—N5—Ni1	158.1 (3)	N3—C10'—H10D	109.5
N1—C1—C2	121.8 (3)	N3—C10'—H10E	109.5
N1—C1—H1	119.1	H10D—C10'—H10E	109.5
C2—C1—H1	119.1	N3—C10'—H10F	109.5
C3—C2—C1	118.9 (3)	H10D—C10'—H10F	109.5
C3—C2—H2	120.5	H10E—C10'—H10F	109.5
C1—C2—H2	120.5	N3—C11'—H11D	109.5
C2—C3—C4	119.9 (3)	N3—C11'—H11E	109.5
C2—C3—H3	120.0	H11D—C11'—H11E	109.5
C4—C3—H3	120.0	N3—C11'—H11F	109.5
C3—C4—C5	118.3 (3)	H11D—C11'—H11F	109.5
C3—C4—H4	120.8	H11E—C11'—H11F	109.5
C5—C4—H4	120.8	N4—C12—S1	179.1 (3)
N1—C5—C4	121.9 (3)	N5—C13—S2	177.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C1–C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···S1ⁱ	0.82 (2)	2.38 (2)	3.181 (3)	164 (4)
O1—H1A···S2ⁱⁱ	0.84 (2)	2.35 (2)	3.190 (3)	178 (4)
C7—H7C···Cg1ⁱⁱⁱ	0.98	2.88	3.531 (3)	125

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ni(NCS)₂(C₁₁H₁₇N₃)(H₂O)]
M_r	384.16
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	12.8404 (2), 14.2623 (3), 9.5868 (2)
β (°)	99.467 (1)
V (Å³)	1731.75 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.37
Crystal size (mm)	0.22 × 0.19 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.753, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	7792, 3698, 3451
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.070, 1.02
No. of reflections	3698
No. of parameters	234
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.52
Absolute structure	Flack (1983), 1798 Friedel pairs
Absolute structure parameter	0.020 (11)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C1–C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···S1ⁱ	0.824 (19)	2.38 (2)	3.181 (3)	164 (4)
O1—H1A···S2ⁱⁱ	0.836 (18)	2.354 (19)	3.190 (3)	178 (4)
C7—H7C···Cg1ⁱⁱⁱ	0.98	2.88	3.531 (3)	125

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) x, −y+2, z−1/2.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP004/2010B).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bhowmik, P., Chattopadhyay, S., Drew, M. G. B., Diaz, D. & Ghosh, A. (2010). Polyhedron, 29, 2637–2642. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diao, Y.-P. (2007). Acta Cryst. E63, m1453–m1454. Web of Science CSD CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science 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
Suleiman Gwaram, N., Ikmal Hisham, N. A., Khaledi, H. & Mohd Ali, H. (2011). Acta Cryst. E67, m108. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 4| April 2011| Page m513

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