Azido­{1-[(2-diethyl­amino­ethyl­imino-κ²N,N′)meth­yl]naphthalen-2-olato-κO}nickel(II)

In the title mononuclear nickel(II) complex, [Ni(C₁₇H₂₁N₂O)(N₃)], the Ni^II atom is four-coordinated by the phenolate O, imine N and amine N atoms of one Schiff base ligand, and by the terminal N atom of an azido ligand, forming a square-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.055
• wR factor = 0.152
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C13
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N2

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.04
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.60 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C14     ..       5.65 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.67 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C17     ..       6.81 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT410_ALERT_2_C Short Intra H...H Contact  H9     ..  H11     ..       1.99 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       1.99

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Nickel(II) complexes with Schiff base ligands have received much attention in recent years (Marganian et al., 1995). Some of the complexes have been found to have pharmacological and antitumor properties (Harrop et al., 2003; Brückner et al., 2000; Ren et al., 2002). Nickel is also present in the active sites of several important classes of metalloproteins, as either a homodinuclear or a heterodinuclear species. We have recently reported a few transition metal complexes (Diao, Huang et al., 2007; Diao, Shu et al., 2007; Diao, 2007a,b; Li, Huang et al., 2007). In order to further develop the coordination chemistry of such nickel complexes, the author report herein the title new nickel(II) compound.

The Ni^II atom in the mononuclear complex is four-coordinate in a square-planar geometry with one phenolate O, one imine N, and one amine N atoms of one Schiff base ligand and one terminal N atom of an azido ligand (Fig. 1). All the bond values (Table 1) subtended at the metal centre are comparable with the values observed in other Schiff base nickel(II) complexes (Arıcı et al., 2005; Usman et al., 2003; Van Hecke et al., 2007; Li, Jiang, et al., 2007).

Related literature

For related literature, see: Arıcı et al. (2005); Brückner et al. (2000); Diao (2007a,b); Diao, Huang et al. (2007); Diao, Shu et al. (2007); Harrop et al. (2003); Li, Huang et al. (2007); Li, Jiang et al. (2007); Marganian et al. (1995); Ren et al. (2002); Usman et al. (2003); Van Hecke et al. (2007).

S2. Experimental

2-Hydroxy-1-naphthaldehyde (0.1 mmol, 17.0 mg), N,N-diethylethane-1,2-diamine (0.1 mmol, 11.6 mg), sodium azide (0.1 mmol, 6.5 mg), and Ni(NO₃)₂.6H₂O (0.1 mmol, 29.0 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature for 30 min to give a red solution. After keeping the solution in air for a week, red block-like crystals were formed.

S3. Refinement

H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

Fig. 1. The structure of the complex with 30% probability level.

Azido{1-[(2-diethylaminoethylimino-κ²N,N')methyl]νaphthalen-2-olato-κO}nickel(II)

Crystal data

[Ni(C17H21N2O)(N3)]	F(000) = 1552
Mr = 370.10	Dx = 1.460 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1780 reflections
a = 7.220 (2) Å	θ = 2.3–24.9°
b = 13.873 (2) Å	µ = 1.17 mm^−1
c = 33.630 (5) Å	T = 293 K
V = 3368.5 (12) Å^3	Block, red
Z = 8	0.21 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4062 independent reflections
Radiation source: fine-focus sealed tube	2839 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ω scans	θmax = 28.3°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.792, Tmax = 0.826	k = −18→18
27240 measured reflections	l = −43→43

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0662P)^2 + 3.967P] where P = (Fo^2 + 2Fc^2)/3
4062 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.94 e Å^−3
0 restraints	Δρmin = −0.46 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	0.10100 (7)	0.01095 (3)	0.117402 (13)	0.04055 (17)
N1	0.1712 (4)	0.11724 (19)	0.15022 (8)	0.0424 (7)
N2	0.1712 (5)	0.1004 (2)	0.07048 (9)	0.0487 (7)
N3	−0.0160 (7)	−0.0798 (3)	0.08122 (10)	0.0784 (13)
N4	−0.1139 (5)	−0.1430 (2)	0.09152 (10)	0.0558 (8)
N5	−0.2081 (7)	−0.2050 (3)	0.09994 (13)	0.0875 (13)
O1	0.0936 (4)	−0.07559 (17)	0.16059 (7)	0.0481 (6)
C1	0.1457 (4)	0.0368 (2)	0.21414 (10)	0.0373 (7)
C2	0.1026 (4)	−0.0545 (2)	0.19821 (10)	0.0392 (7)
C3	0.0660 (5)	−0.1322 (3)	0.22519 (12)	0.0479 (9)
H3	0.0359	−0.1926	0.2151	0.058*
C4	0.0744 (5)	−0.1194 (3)	0.26479 (12)	0.0521 (10)
H4	0.0497	−0.1715	0.2813	0.063*
C5	0.1195 (5)	−0.0292 (3)	0.28224 (11)	0.0456 (8)
C6	0.1306 (6)	−0.0175 (3)	0.32361 (12)	0.0586 (11)
H6	0.1093	−0.0702	0.3401	0.070*
C7	0.1721 (6)	0.0696 (3)	0.34026 (12)	0.0631 (12)
H7	0.1806	0.0760	0.3677	0.076*
C8	0.2015 (6)	0.1485 (3)	0.31570 (11)	0.0576 (10)
H8	0.2274	0.2083	0.3269	0.069*
C9	0.1929 (5)	0.1393 (3)	0.27510 (10)	0.0468 (8)
H9	0.2141	0.1932	0.2593	0.056*
C10	0.1527 (4)	0.0502 (2)	0.25674 (10)	0.0393 (7)
C11	0.1831 (5)	0.1166 (2)	0.18845 (10)	0.0416 (8)
H11	0.2198	0.1738	0.2006	0.050*
C12	0.2103 (8)	0.2060 (3)	0.12847 (12)	0.0678 (13)
H12A	0.3084	0.2415	0.1416	0.081*
H12B	0.1006	0.2463	0.1277	0.081*
C13	0.2670 (9)	0.1810 (4)	0.08795 (12)	0.096 (2)
H13A	0.2484	0.2369	0.0711	0.115*
H13B	0.3985	0.1669	0.0881	0.115*
C14	−0.0127 (8)	0.1295 (4)	0.05226 (16)	0.0866 (15)
H14A	−0.0756	0.0716	0.0433	0.104*
H14B	−0.0886	0.1583	0.0729	0.104*
C15	−0.0020 (11)	0.1982 (5)	0.01826 (17)	0.120 (2)
H15A	0.0504	0.2580	0.0272	0.180*
H15B	−0.1241	0.2095	0.0080	0.180*
H15C	0.0746	0.1713	−0.0023	0.180*
C16	0.2778 (10)	0.0477 (4)	0.03984 (16)	0.103 (2)
H16A	0.3318	0.0940	0.0216	0.123*
H16B	0.1935	0.0073	0.0248	0.123*
C17	0.4310 (8)	−0.0148 (4)	0.05682 (19)	0.0935 (18)
H17A	0.5317	0.0253	0.0654	0.140*
H17B	0.4741	−0.0586	0.0367	0.140*
H17C	0.3842	−0.0508	0.0791	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0491 (3)	0.0340 (2)	0.0385 (3)	−0.00497 (18)	0.0024 (2)	−0.00653 (17)
N1	0.0514 (17)	0.0356 (14)	0.0403 (15)	−0.0052 (13)	0.0045 (13)	−0.0020 (12)
N2	0.063 (2)	0.0446 (17)	0.0389 (15)	0.0036 (15)	0.0034 (14)	−0.0018 (13)
N3	0.120 (4)	0.069 (2)	0.0454 (19)	−0.043 (3)	0.000 (2)	−0.0101 (17)
N4	0.068 (2)	0.0485 (19)	0.0505 (19)	−0.0078 (18)	−0.0106 (16)	−0.0050 (15)
N5	0.100 (3)	0.071 (3)	0.092 (3)	−0.037 (3)	−0.012 (3)	0.000 (2)
O1	0.0604 (16)	0.0374 (13)	0.0465 (14)	−0.0046 (11)	0.0002 (12)	−0.0067 (10)
C1	0.0311 (16)	0.0357 (16)	0.0451 (18)	0.0043 (13)	−0.0009 (13)	−0.0002 (14)
C2	0.0328 (17)	0.0363 (17)	0.0485 (19)	0.0024 (14)	0.0016 (14)	0.0004 (14)
C3	0.043 (2)	0.0355 (18)	0.065 (2)	−0.0026 (15)	0.0022 (17)	0.0066 (16)
C4	0.046 (2)	0.047 (2)	0.063 (2)	0.0017 (16)	0.0053 (18)	0.0171 (18)
C5	0.0351 (19)	0.054 (2)	0.047 (2)	0.0109 (15)	0.0023 (15)	0.0055 (16)
C6	0.053 (2)	0.073 (3)	0.050 (2)	0.013 (2)	0.0040 (18)	0.018 (2)
C7	0.059 (3)	0.089 (3)	0.041 (2)	0.020 (2)	0.0017 (18)	0.001 (2)
C8	0.061 (3)	0.065 (3)	0.047 (2)	0.006 (2)	0.0017 (19)	−0.0099 (19)
C9	0.051 (2)	0.047 (2)	0.0424 (19)	0.0056 (17)	0.0020 (16)	−0.0038 (15)
C10	0.0299 (16)	0.0438 (17)	0.0441 (19)	0.0068 (14)	0.0009 (14)	−0.0003 (15)
C11	0.044 (2)	0.0346 (17)	0.0460 (19)	−0.0003 (14)	0.0041 (15)	−0.0058 (14)
C12	0.114 (4)	0.039 (2)	0.050 (2)	−0.011 (2)	0.011 (2)	0.0002 (17)
C13	0.156 (5)	0.083 (3)	0.050 (3)	−0.071 (4)	−0.006 (3)	0.007 (2)
C14	0.101 (4)	0.074 (3)	0.084 (4)	−0.001 (3)	−0.019 (3)	0.006 (3)
C15	0.162 (7)	0.118 (5)	0.080 (4)	0.017 (5)	−0.037 (4)	0.012 (4)
C16	0.134 (6)	0.094 (4)	0.080 (4)	0.011 (4)	0.045 (4)	0.006 (3)
C17	0.094 (4)	0.093 (4)	0.094 (4)	0.028 (3)	0.023 (3)	−0.004 (3)

Geometric parameters (Å, º)

Ni1—O1	1.885 (2)	C7—C8	1.387 (6)
Ni1—N1	1.910 (3)	C7—H7	0.9300
Ni1—N3	1.944 (3)	C8—C9	1.373 (5)
Ni1—N2	2.071 (3)	C8—H8	0.9300
N1—C11	1.289 (4)	C9—C10	1.412 (5)
N1—C12	1.459 (5)	C9—H9	0.9300
N2—C13	1.440 (5)	C11—H11	0.9300
N2—C16	1.479 (6)	C12—C13	1.465 (6)
N2—C14	1.517 (6)	C12—H12A	0.9700
N3—N4	1.179 (5)	C12—H12B	0.9700
N4—N5	1.132 (5)	C13—H13A	0.9700
O1—C2	1.300 (4)	C13—H13B	0.9700
C1—C2	1.410 (5)	C14—C15	1.490 (7)
C1—C11	1.430 (5)	C14—H14A	0.9700
C1—C10	1.446 (5)	C14—H14B	0.9700
C2—C3	1.433 (5)	C15—H15A	0.9600
C3—C4	1.345 (5)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.420 (5)	C16—C17	1.518 (8)
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.403 (6)	C16—H16B	0.9700
C5—C10	1.417 (5)	C17—H17A	0.9600
C6—C7	1.365 (6)	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
O1—Ni1—N1	93.10 (11)	C10—C9—H9	119.2
O1—Ni1—N3	93.28 (13)	C9—C10—C5	116.8 (3)
N1—Ni1—N3	167.63 (17)	C9—C10—C1	123.6 (3)
O1—Ni1—N2	167.40 (12)	C5—C10—C1	119.6 (3)
N1—Ni1—N2	84.99 (12)	N1—C11—C1	126.5 (3)
N3—Ni1—N2	91.01 (14)	N1—C11—H11	116.7
C11—N1—C12	119.5 (3)	C1—C11—H11	116.7
C11—N1—Ni1	126.1 (2)	N1—C12—C13	108.7 (3)
C12—N1—Ni1	114.4 (2)	N1—C12—H12A	109.9
C13—N2—C16	114.7 (4)	C13—C12—H12A	109.9
C13—N2—C14	112.3 (4)	N1—C12—H12B	109.9
C16—N2—C14	107.8 (4)	C13—C12—H12B	109.9
C13—N2—Ni1	105.8 (2)	H12A—C12—H12B	108.3
C16—N2—Ni1	111.2 (3)	N2—C13—C12	115.4 (4)
C14—N2—Ni1	104.7 (3)	N2—C13—H13A	108.4
N4—N3—Ni1	124.0 (3)	C12—C13—H13A	108.4
N5—N4—N3	177.4 (4)	N2—C13—H13B	108.4
C2—O1—Ni1	127.2 (2)	C12—C13—H13B	108.4
C2—C1—C11	120.5 (3)	H13A—C13—H13B	107.5
C2—C1—C10	120.0 (3)	C15—C14—N2	115.7 (5)
C11—C1—C10	119.5 (3)	C15—C14—H14A	108.3
O1—C2—C1	125.7 (3)	N2—C14—H14A	108.3
O1—C2—C3	115.9 (3)	C15—C14—H14B	108.3
C1—C2—C3	118.4 (3)	N2—C14—H14B	108.3
C4—C3—C2	121.3 (3)	H14A—C14—H14B	107.4
C4—C3—H3	119.3	C14—C15—H15A	109.5
C2—C3—H3	119.3	C14—C15—H15B	109.5
C3—C4—C5	122.4 (3)	H15A—C15—H15B	109.5
C3—C4—H4	118.8	C14—C15—H15C	109.5
C5—C4—H4	118.8	H15A—C15—H15C	109.5
C6—C5—C10	120.0 (4)	H15B—C15—H15C	109.5
C6—C5—C4	121.7 (4)	N2—C16—C17	113.6 (5)
C10—C5—C4	118.3 (3)	N2—C16—H16A	108.9
C7—C6—C5	121.5 (4)	C17—C16—H16A	108.9
C7—C6—H6	119.3	N2—C16—H16B	108.9
C5—C6—H6	119.3	C17—C16—H16B	108.9
C6—C7—C8	119.2 (4)	H16A—C16—H16B	107.7
C6—C7—H7	120.4	C16—C17—H17A	109.5
C8—C7—H7	120.4	C16—C17—H17B	109.5
C9—C8—C7	120.8 (4)	H17A—C17—H17B	109.5
C9—C8—H8	119.6	C16—C17—H17C	109.5
C7—C8—H8	119.6	H17A—C17—H17C	109.5
C8—C9—C10	121.7 (4)	H17B—C17—H17C	109.5
C8—C9—H9	119.2