{1-[2-(Dimethyl­amino)ethyl­imino­meth­yl]-2-naphtholato}thio­cyanato­nickel(II)

The title compound, [Ni(C₁₅H₁₇N₂O)(NCS)], is a mononuclear Schiff base nickel(II) complex. The Ni^II atom is coordinated by one O and two N atoms of the Schiff base ligand, and by one N atom of the thio­cyanate ligand, forming a square-planar coordination.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.062
• wR factor = 0.151
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Schiff base complexes are of great interest in coordination chemistry (Goswami & Eichhorn, 1999; Dominguez-Vera et al., 1998; Bernardo et al., 1996). Recently, we have reported a few Schiff base complexes (You, 2005a,b,c,d,e,f; You & Zhu, 2005a,b). As an extension of our work on the structural characterization of Schiff base complexes, the novel title Schiff base nickel(II) complex, (I), is reported.

Complex (I) is a mononuclear nickel(II) compound (Fig. 1). The Ni atom is four-coordinated in a slightly distorted square-planar coordination by one O and two N atoms of the Schiff base ligand, and by one N atom of the thiocyanate anion (Table 1). The Ni—O and Ni—N bond lengths are comparable to the corresponding values observed in other Schiff base nickel(II) complexes (You, 2005g,h,i) and, as expected, the bond involving amine atom N2 is longer than that involving imine atom N1. The thiocyanate group is nearly linear and shows almost linear coordination to the metal atom.

S2. Experimental

2-Hydroxy-1-naphthaldehyde (0.2 mmol, 17.2 mg) and N,N-dimethylethane-1,2-diamine (0.2 mmol, 17.6 mg) were dissolved in MeOH (10 ml). The mixture was stirred for 20 min to give a clear yellow solution. To the solution were added an aqueous solution (5 ml) of NH₄NCS (0.1 mmol, 7.6 mg) and an MeOH solution (10 ml) of Ni(ClO₄)₂·7H₂O (0.1 mmol, 38.4 mg), with stirring. The mixture was stirred at room temperature for about 30 min and filtered. After keeping the green filtrate in air for 7 d, green block-shaped crystals were formed.

S3. Refinement

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.96 Å, and with U_iso(H) = 1.2 or 1.5U_eq(C).

Computing details

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

Figures

Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

{1-[2-(Dimethylamino)ethyliminomethyl]-2-naphthalato}thiocyanatonickel(II)

Crystal data

[Ni(C15H17N2O)(NCS)]	F(000) = 744
Mr = 358.10	Dx = 1.496 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.413 (2) Å	Cell parameters from 1147 reflections
b = 6.167 (2) Å	θ = 2.5–21.3°
c = 30.683 (6) Å	µ = 1.36 mm^−1
β = 93.04 (3)°	T = 298 K
V = 1589.7 (7) Å^3	Block, green
Z = 4	0.31 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3617 independent reflections
Radiation source: fine-focus sealed tube	2051 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.679, Tmax = 0.802	k = −8→8
12963 measured reflections	l = −39→39

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0615P)^2] where P = (Fo^2 + 2Fc^2)/3
3617 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.73977 (7)	0.30340 (10)	0.106195 (18)	0.0417 (2)
S1	0.23326 (18)	0.0588 (3)	0.06465 (6)	0.0832 (5)
O1	0.7474 (4)	0.0726 (5)	0.14312 (10)	0.0495 (8)
N1	0.9231 (4)	0.4202 (6)	0.13116 (12)	0.0409 (9)
N2	0.7465 (5)	0.5259 (6)	0.06227 (12)	0.0467 (10)
N3	0.5415 (5)	0.2030 (7)	0.08382 (14)	0.0587 (11)
C1	0.9453 (5)	0.2008 (7)	0.19585 (14)	0.0381 (10)
C2	0.8339 (5)	0.0494 (7)	0.17941 (16)	0.0428 (11)
C3	0.8105 (6)	−0.1459 (7)	0.20316 (17)	0.0488 (12)
H3	0.7445	−0.2537	0.1911	0.059*
C4	0.8831 (6)	−0.1753 (8)	0.24283 (18)	0.0522 (13)
H4	0.8683	−0.3056	0.2573	0.063*
C5	0.9820 (5)	−0.0140 (8)	0.26339 (15)	0.0438 (12)
C6	1.0359 (6)	−0.0344 (9)	0.30716 (18)	0.0585 (15)
H6	1.0131	−0.1599	0.3224	0.070*
C7	1.1211 (6)	0.1263 (10)	0.32766 (18)	0.0630 (16)
H7	1.1530	0.1129	0.3570	0.076*
C8	1.1605 (6)	0.3114 (9)	0.30449 (17)	0.0600 (14)
H8	1.2205	0.4204	0.3184	0.072*
C9	1.1115 (6)	0.3339 (8)	0.26136 (16)	0.0503 (13)
H9	1.1412	0.4564	0.2461	0.060*
C10	1.0175 (5)	0.1756 (7)	0.23998 (15)	0.0405 (11)
C11	0.9900 (5)	0.3736 (7)	0.16859 (15)	0.0414 (11)
H11	1.0747	0.4603	0.1786	0.050*
C12	0.9947 (6)	0.5860 (9)	0.10361 (17)	0.0614 (15)
H12A	1.0510	0.6926	0.1218	0.074*
H12B	1.0701	0.5188	0.0850	0.074*
C13	0.8685 (8)	0.6906 (9)	0.07712 (19)	0.0787 (19)
H13A	0.9127	0.7588	0.0520	0.094*
H13B	0.8189	0.8023	0.0941	0.094*
C14	0.5971 (7)	0.6478 (9)	0.0534 (2)	0.0801 (19)
H14A	0.6148	0.7623	0.0331	0.120*
H14B	0.5628	0.7085	0.0802	0.120*
H14C	0.5165	0.5517	0.0413	0.120*
C15	0.7928 (7)	0.4197 (10)	0.02182 (17)	0.0729 (17)
H15A	0.7152	0.3117	0.0132	0.109*
H15B	0.8950	0.3523	0.0268	0.109*
H15C	0.7983	0.5260	−0.0009	0.109*
C16	0.4138 (6)	0.1419 (7)	0.07604 (16)	0.0497 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0423 (4)	0.0390 (4)	0.0433 (4)	−0.0058 (3)	−0.0021 (3)	−0.0037 (3)
S1	0.0503 (9)	0.0790 (11)	0.1182 (14)	−0.0186 (8)	−0.0154 (9)	0.0132 (10)
O1	0.054 (2)	0.0419 (19)	0.052 (2)	−0.0156 (16)	−0.0072 (17)	0.0007 (16)
N1	0.040 (2)	0.040 (2)	0.042 (2)	−0.0093 (18)	−0.0027 (18)	0.0052 (18)
N2	0.054 (3)	0.048 (2)	0.037 (2)	−0.007 (2)	−0.0035 (19)	0.0002 (19)
N3	0.050 (3)	0.062 (3)	0.064 (3)	−0.011 (2)	−0.003 (2)	0.001 (2)
C1	0.037 (2)	0.034 (2)	0.044 (3)	0.001 (2)	0.008 (2)	0.005 (2)
C2	0.042 (3)	0.036 (3)	0.051 (3)	−0.003 (2)	0.011 (2)	−0.004 (2)
C3	0.052 (3)	0.035 (3)	0.060 (3)	−0.006 (2)	0.007 (3)	0.001 (2)
C4	0.047 (3)	0.040 (3)	0.071 (4)	0.004 (2)	0.015 (3)	0.020 (3)
C5	0.035 (3)	0.049 (3)	0.049 (3)	0.021 (2)	0.013 (2)	0.010 (2)
C6	0.044 (3)	0.067 (4)	0.066 (4)	0.015 (3)	0.011 (3)	0.024 (3)
C7	0.040 (3)	0.099 (5)	0.049 (3)	0.018 (3)	−0.001 (2)	0.021 (3)
C8	0.043 (3)	0.077 (4)	0.058 (3)	0.004 (3)	−0.008 (2)	−0.001 (3)
C9	0.049 (3)	0.052 (3)	0.049 (3)	0.005 (2)	−0.003 (2)	0.006 (3)
C10	0.031 (2)	0.042 (3)	0.049 (3)	0.007 (2)	0.012 (2)	0.004 (2)
C11	0.035 (3)	0.037 (3)	0.052 (3)	−0.008 (2)	0.000 (2)	0.000 (2)
C12	0.064 (4)	0.066 (4)	0.053 (3)	−0.031 (3)	−0.012 (3)	0.023 (3)
C13	0.103 (5)	0.062 (4)	0.067 (4)	−0.036 (4)	−0.028 (3)	0.021 (3)
C14	0.085 (5)	0.069 (4)	0.087 (4)	0.026 (3)	0.004 (4)	0.015 (3)
C15	0.088 (5)	0.075 (4)	0.056 (4)	0.007 (3)	0.011 (3)	0.000 (3)
C16	0.053 (3)	0.043 (3)	0.053 (3)	−0.005 (2)	−0.002 (3)	0.004 (2)

Geometric parameters (Å, º)

Ni1—O1	1.818 (3)	C5—C10	1.413 (6)
Ni1—N1	1.833 (4)	C6—C7	1.358 (7)
Ni1—N3	1.875 (4)	C6—H6	0.930
Ni1—N2	1.926 (4)	C7—C8	1.394 (7)
S1—C16	1.623 (5)	C7—H7	0.930
O1—C2	1.305 (5)	C8—C9	1.372 (7)
N1—C11	1.285 (5)	C8—H8	0.930
N1—C12	1.476 (5)	C9—C10	1.398 (6)
N2—C15	1.474 (6)	C9—H9	0.930
N2—C14	1.477 (6)	C11—H11	0.930
N2—C13	1.497 (6)	C12—C13	1.453 (7)
N3—C16	1.152 (6)	C12—H12A	0.970
C1—C2	1.398 (6)	C12—H12B	0.970
C1—C11	1.418 (6)	C13—H13A	0.970
C1—C10	1.462 (6)	C13—H13B	0.970
C2—C3	1.427 (6)	C14—H14A	0.960
C3—C4	1.345 (7)	C14—H14B	0.960
C3—H3	0.930	C14—H14C	0.960
C4—C5	1.422 (7)	C15—H15A	0.960
C4—H4	0.930	C15—H15B	0.960
C5—C6	1.400 (7)	C15—H15C	0.960
O1—Ni1—N1	92.64 (15)	C9—C8—C7	120.5 (5)
O1—Ni1—N3	88.33 (17)	C9—C8—H8	119.8
N1—Ni1—N3	174.52 (18)	C7—C8—H8	119.8
O1—Ni1—N2	172.86 (16)	C8—C9—C10	121.1 (5)
N1—Ni1—N2	87.54 (16)	C8—C9—H9	119.5
N3—Ni1—N2	92.16 (17)	C10—C9—H9	119.5
C2—O1—Ni1	128.1 (3)	C9—C10—C5	118.0 (4)
C11—N1—C12	119.6 (4)	C9—C10—C1	123.9 (4)
C11—N1—Ni1	127.2 (3)	C5—C10—C1	118.0 (4)
C12—N1—Ni1	113.1 (3)	N1—C11—C1	125.3 (4)
C15—N2—C14	109.4 (4)	N1—C11—H11	117.3
C15—N2—C13	110.5 (5)	C1—C11—H11	117.3
C14—N2—C13	105.9 (4)	C13—C12—N1	108.6 (4)
C15—N2—Ni1	106.9 (3)	C13—C12—H12A	110.0
C14—N2—Ni1	115.7 (3)	N1—C12—H12A	110.0
C13—N2—Ni1	108.4 (3)	C13—C12—H12B	110.0
C16—N3—Ni1	170.4 (4)	N1—C12—H12B	110.0
C2—C1—C11	118.9 (4)	H12A—C12—H12B	108.3
C2—C1—C10	120.1 (4)	C12—C13—N2	109.7 (4)
C11—C1—C10	121.0 (4)	C12—C13—H13A	109.7
O1—C2—C1	124.6 (4)	N2—C13—H13A	109.7
O1—C2—C3	116.3 (4)	C12—C13—H13B	109.7
C1—C2—C3	119.2 (5)	N2—C13—H13B	109.7
C4—C3—C2	120.5 (5)	H13A—C13—H13B	108.2
C4—C3—H3	119.7	N2—C14—H14A	109.5
C2—C3—H3	119.7	N2—C14—H14B	109.5
C3—C4—C5	122.3 (5)	H14A—C14—H14B	109.5
C3—C4—H4	118.9	N2—C14—H14C	109.5
C5—C4—H4	118.9	H14A—C14—H14C	109.5
C6—C5—C10	119.7 (5)	H14B—C14—H14C	109.5
C6—C5—C4	121.0 (5)	N2—C15—H15A	109.5
C10—C5—C4	119.2 (4)	N2—C15—H15B	109.5
C7—C6—C5	121.0 (5)	H15A—C15—H15B	109.5
C7—C6—H6	119.5	N2—C15—H15C	109.5
C5—C6—H6	119.5	H15A—C15—H15C	109.5
C6—C7—C8	119.7 (5)	H15B—C15—H15C	109.5
C6—C7—H7	120.1	N3—C16—S1	179.2 (5)
C8—C7—H7	120.1