Bis{1-[(4-methoxy­phen­yl)amino]-2-methyl­glyoximato-κ²N,N′}nickel(II)

The title mol­ecule, [Ni(C₁₀H₁₂N₃O₃)₂], possesses a crystallographic centre of symmetry at the Ni^II atom. The coordin­ation geometry around the Ni^II atom is distorted square planar, consisting of four N atoms from two oxime ligands. The crystal packing shows two-dimensional polymeric chains, which are stabilized by a hydrogen-bonded network, and other weak inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis{1-[(4-methoxyphenyl)amino]-2-methylglyoximato-κ²N,N'}nickel(II)

Crystal data

[Ni(C10H12N3O3)2]	F(000) = 524
Mr = 503.16	Dx = 1.541 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8326 reflections
a = 8.8819 (7) Å	θ = 1.8–26.1°
b = 5.2497 (3) Å	µ = 0.95 mm^−1
c = 24.216 (2) Å	T = 293 K
β = 106.165 (7)°	Plate, red
V = 1084.49 (14) Å^3	0.35 × 0.30 × 0.28 mm
Z = 2

Data collection

Stoe IPDS-2 diffractometer	1916 independent reflections
Radiation source: fine-focus sealed tube	1525 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 1.8°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→6
Tmin = 0.559, Tmax = 0.928	l = −28→28
13231 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.1755P] where P = (Fo^2 + 2Fc^2)/3
1916 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.34 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	0.0000	0.0000	0.0000	0.04277 (16)
O2	−0.08383 (19)	0.3661 (4)	0.07118 (8)	0.0562 (5)
O1	0.2985 (2)	−0.0808 (4)	−0.02111 (9)	0.0630 (6)
O3	0.7991 (3)	0.5024 (5)	0.27763 (10)	0.0900 (8)
N1	0.2086 (2)	0.0608 (4)	0.00550 (9)	0.0476 (5)
N2	0.0317 (2)	0.2652 (4)	0.05319 (8)	0.0456 (5)
N3	0.4345 (3)	0.2774 (5)	0.05581 (11)	0.0589 (6)
C1	0.2790 (3)	0.2268 (5)	0.04354 (10)	0.0456 (6)
C2	0.1719 (3)	0.3618 (5)	0.06993 (10)	0.0454 (6)
C3	0.2096 (3)	0.5929 (6)	0.10620 (12)	0.0566 (7)
H3A	0.1156	0.6895	0.1027	0.085*
H3B	0.2837	0.6950	0.0938	0.085*
H3C	0.2539	0.5441	0.1456	0.085*
C4	0.5282 (3)	0.3440 (5)	0.11233 (11)	0.0508 (6)
C5	0.6383 (3)	0.5330 (6)	0.11941 (13)	0.0600 (7)
H5	0.6511	0.6214	0.0878	0.072*
C6	0.7324 (3)	0.5923 (7)	0.17556 (13)	0.0652 (5)
H6	0.8081	0.7194	0.1810	0.078*
C7	0.7112 (3)	0.4614 (6)	0.22147 (14)	0.0652 (5)
C8	0.6003 (3)	0.2753 (6)	0.21446 (13)	0.0652 (5)
H8	0.5859	0.1897	0.2462	0.078*
C9	0.5105 (3)	0.2157 (6)	0.16027 (13)	0.0626 (8)
H9	0.4361	0.0868	0.1555	0.075*
C10	0.9134 (4)	0.6923 (9)	0.28827 (16)	0.0967 (13)
H10A	0.9611	0.7060	0.3289	0.145*
H10B	0.8659	0.8520	0.2738	0.145*
H10C	0.9919	0.6496	0.2694	0.145*
H3	0.479 (4)	0.207 (7)	0.0348 (16)	0.090 (13)*
H1	0.210 (5)	−0.208 (8)	−0.0456 (18)	0.117 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0301 (2)	0.0580 (3)	0.0381 (2)	0.0019 (2)	0.00599 (16)	−0.0080 (2)
O2	0.0384 (9)	0.0711 (12)	0.0595 (11)	0.0046 (9)	0.0141 (8)	−0.0198 (10)
O1	0.0361 (9)	0.0871 (15)	0.0681 (13)	−0.0021 (9)	0.0181 (9)	−0.0309 (11)
O3	0.0726 (15)	0.128 (2)	0.0593 (13)	−0.0194 (14)	0.0011 (11)	−0.0100 (14)
N1	0.0368 (10)	0.0602 (15)	0.0454 (11)	0.0020 (9)	0.0110 (9)	−0.0116 (10)
N2	0.0345 (10)	0.0598 (13)	0.0410 (11)	0.0049 (9)	0.0077 (8)	−0.0047 (10)
N3	0.0359 (11)	0.0863 (18)	0.0548 (14)	−0.0078 (11)	0.0131 (10)	−0.0207 (13)
C1	0.0357 (11)	0.0557 (15)	0.0433 (13)	−0.0001 (11)	0.0078 (10)	−0.0012 (12)
C2	0.0397 (13)	0.0530 (15)	0.0403 (13)	0.0025 (11)	0.0060 (10)	−0.0001 (11)
C3	0.0519 (15)	0.0553 (16)	0.0581 (17)	0.0001 (13)	0.0080 (13)	−0.0079 (13)
C4	0.0341 (12)	0.0631 (18)	0.0528 (15)	−0.0001 (12)	0.0085 (11)	−0.0131 (13)
C5	0.0493 (15)	0.072 (2)	0.0606 (16)	−0.0111 (13)	0.0190 (12)	−0.0121 (14)
C6	0.0524 (9)	0.0768 (12)	0.0626 (10)	−0.0036 (8)	0.0096 (8)	−0.0051 (9)
C7	0.0524 (9)	0.0768 (12)	0.0626 (10)	−0.0036 (8)	0.0096 (8)	−0.0051 (9)
C8	0.0524 (9)	0.0768 (12)	0.0626 (10)	−0.0036 (8)	0.0096 (8)	−0.0051 (9)
C9	0.0495 (15)	0.0622 (18)	0.0707 (19)	−0.0045 (13)	0.0078 (14)	0.0009 (15)
C10	0.074 (2)	0.123 (3)	0.082 (3)	−0.017 (2)	0.0027 (19)	−0.039 (2)

Geometric parameters (Å, º)

Ni1—N1	1.848 (2)	C3—H3B	0.9600
Ni1—N2	1.864 (2)	C3—H3C	0.9600
O2—N2	1.332 (3)	C4—C5	1.370 (4)
O1—N1	1.376 (3)	C4—C9	1.388 (4)
O1—H1	1.07 (4)	C5—C6	1.418 (4)
O3—C7	1.383 (4)	C5—H5	0.9300
O3—C10	1.395 (4)	C6—C7	1.364 (5)
N1—C1	1.295 (3)	C6—H6	0.9300
N2—C2	1.300 (3)	C7—C8	1.363 (4)
N3—C1	1.356 (3)	C8—C9	1.369 (4)
N3—C4	1.433 (3)	C8—H8	0.9300
N3—H3	0.81 (4)	C9—H9	0.9300
C1—C2	1.468 (4)	C10—H10A	0.9600
C2—C3	1.480 (4)	C10—H10B	0.9600
C3—H3A	0.9600	C10—H10C	0.9600
N1^i—Ni1—N1	180.00 (13)	H3B—C3—H3C	109.5
N1^i—Ni1—N2	97.73 (9)	C5—C4—C9	119.3 (3)
N1—Ni1—N2	82.27 (9)	C5—C4—N3	120.0 (3)
N2—Ni1—N2^i	180.00 (9)	C9—C4—N3	120.6 (2)
N1—O1—H1	100 (2)	C4—C5—C6	119.3 (3)
C7—O3—C10	118.4 (3)	C4—C5—H5	120.4
C1—N1—O1	117.9 (2)	C6—C5—H5	120.4
C1—N1—Ni1	116.30 (17)	C7—C6—C5	119.5 (3)
O1—N1—Ni1	125.04 (15)	C7—C6—H6	120.3
C2—N2—O2	120.1 (2)	C5—C6—H6	120.3
C2—N2—Ni1	117.04 (17)	C8—C7—C6	121.2 (3)
O2—N2—Ni1	122.76 (15)	C8—C7—O3	115.1 (3)
C1—N3—C4	122.8 (2)	C6—C7—O3	123.7 (3)
C1—N3—H3	115 (3)	C7—C8—C9	119.4 (3)
C4—N3—H3	117 (3)	C7—C8—H8	120.3
N1—C1—N3	123.2 (2)	C9—C8—H8	120.3
N1—C1—C2	113.1 (2)	C8—C9—C4	121.3 (3)
N3—C1—C2	123.7 (2)	C8—C9—H9	119.4
N2—C2—C1	110.9 (2)	C4—C9—H9	119.4
N2—C2—C3	122.9 (2)	O3—C10—H10A	109.5
C1—C2—C3	125.9 (2)	O3—C10—H10B	109.5
C2—C3—H3A	109.5	H10A—C10—H10B	109.5
C2—C3—H3B	109.5	O3—C10—H10C	109.5
H3A—C3—H3B	109.5	H10A—C10—H10C	109.5
C2—C3—H3C	109.5	H10B—C10—H10C	109.5
H3A—C3—H3C	109.5
N2—Ni1—N1—O1	175.4 (2)	N3—C1—C2—C3	9.6 (4)
N1—Ni1—N2—C2	−1.37 (19)	C1—N3—C4—C5	−138.6 (3)
N1—Ni1—N2—O2	174.4 (2)	C1—N3—C4—C9	42.4 (4)
O1—N1—C1—N3	3.9 (4)	C9—C4—C5—C6	0.4 (4)
Ni1—N1—C1—N3	174.7 (2)	N3—C4—C5—C6	−178.5 (3)
O1—N1—C1—C2	−178.7 (2)	C4—C5—C6—C7	−0.4 (5)
Ni1—N1—C1—C2	−7.9 (3)	C5—C6—C7—C8	−0.4 (5)
C4—N3—C1—N1	−146.1 (3)	C5—C6—C7—O3	178.8 (3)
C4—N3—C1—C2	36.8 (4)	C10—O3—C7—C8	−179.2 (3)
O2—N2—C2—C1	−178.2 (2)	C10—O3—C7—C6	1.6 (5)
Ni1—N2—C2—C1	−2.3 (3)	C6—C7—C8—C9	1.1 (5)
O2—N2—C2—C3	−3.7 (4)	O3—C7—C8—C9	−178.1 (3)
Ni1—N2—C2—C3	172.2 (2)	C7—C8—C9—C4	−1.1 (5)
N1—C1—C2—N2	6.5 (3)	C5—C4—C9—C8	0.3 (4)
N3—C1—C2—N2	−176.1 (2)	N3—C4—C9—C8	179.2 (3)
N1—C1—C2—C3	−167.8 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	1.07 (4)	1.39 (5)	2.462 (3)	171 (4)
N3—H3···O1^ii	0.81 (4)	2.19 (4)	2.916 (3)	148 (3)
C10—H10A···O2^iii	0.96	2.51	3.441 (4)	165
N3—H3···O1	0.81 (4)	2.34 (4)	2.685 (3)	106 (3)
C3—H3A···O2	0.96	2.42	2.775 (3)	102

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