{4,4',6,6'-Tetra-iodo-2,2'-[propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato-κ(4)O,N,N',O'}nickel(II).

The asymmetric unit of the title compound, [Ni(C(17)H(12)I(4)N(2)O(2))], comprises half of a Schiff base complex. The Ni(II) and central C atom of the propyl chain are located on a twofold rotation axis. The geometry around the Ni(II) atom is square planar, supported by the N(2)O(2) donor atoms of the coordinated ligand. In the crystal, there are no significant inter-molecular inter-actions present. The crystal studied was a non-merohedral twin with a refined twin component ratio of 0.944 (1):0.056 (1).

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For applications of Schiff bases in coordination chemistry, see, for example: Granovski et al. (1993 ▶); Blower et al. (1998 ▶). For the structure of the Schiff base ligand, see: Kargar et al. (2012a ▶). For related structures, see, for example: Kargar et al. (2012b ▶,c ▶,d ▶,e ▶).

Experimental

Crystal data

[Ni(C17H12I4N2O2)]

M = 842.60

Monoclinic,

a = 26.1229 (18) Å

b = 10.7409 (7) Å

c = 7.2387 (5) Å

β = 98.107 (3)°

V = 2010.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 7.12 mm−1

T = 291 K

0.22 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (TWINABS; Bruker, 2005 ▶) T min = 0.303, T max = 0.600

7468 measured reflections

2188 independent reflections

1755 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.055

S = 1.04

2188 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032138/su2472sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032138/su2472Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C17H12I4N2O2)]	F(000) = 1536
Mr = 842.60	Dx = 2.783 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 526 reflections
a = 26.1229 (18) Å	θ = 2.5–27.5°
b = 10.7409 (7) Å	µ = 7.12 mm−1
c = 7.2387 (5) Å	T = 291 K
β = 98.107 (3)°	Block, red
V = 2010.8 (2) Å3	0.22 × 0.12 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2188 independent reflections
Radiation source: fine-focus sealed tube	1755 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 27.1°, θmin = 1.6°
Absorption correction: multi-scan (TWINABS; Bruker, 2005)	h = −33→33
Tmin = 0.303, Tmax = 0.600	k = −13→13
7463 measured reflections	l = −8→9

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0177P)2 + 2.2669P] where P = (Fo2 + 2Fc2)/3
2188 reflections	(Δ/σ)max = 0.001
120 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.0000	0.48944 (7)	0.2500	0.02132 (18)
I1	0.090843 (12)	0.89044 (3)	0.36252 (5)	0.03652 (10)
I2	0.279631 (12)	0.60955 (3)	0.20407 (5)	0.04421 (11)
N1	0.05062 (13)	0.3679 (3)	0.3138 (5)	0.0242 (8)
O1	0.04733 (11)	0.6174 (2)	0.3090 (4)	0.0269 (7)
C1	0.09612 (15)	0.6129 (4)	0.2932 (6)	0.0224 (9)
C2	0.12636 (16)	0.7229 (4)	0.3024 (6)	0.0240 (9)
C3	0.17729 (16)	0.7234 (4)	0.2769 (6)	0.0291 (10)
H3	0.1954	0.7980	0.2804	0.035*
C4	0.20183 (16)	0.6119 (4)	0.2457 (6)	0.0291 (10)
C5	0.17586 (16)	0.5018 (4)	0.2474 (6)	0.0276 (10)
H5	0.1930	0.4273	0.2327	0.033*
C6	0.12328 (15)	0.5005 (4)	0.2715 (6)	0.0233 (10)
C7	0.09902 (16)	0.3837 (4)	0.3042 (6)	0.0271 (10)
H7	0.1201	0.3136	0.3198	0.033*
C8	0.03503 (17)	0.2492 (4)	0.3903 (6)	0.0292 (10)
H8A	0.0173	0.2661	0.4967	0.035*
H8B	0.0658	0.2012	0.4344	0.035*
C9	0.0000	0.1721 (5)	0.2500	0.0298 (14)
H9A	−0.0212	0.1188	0.3165	0.036*	0.50
H9B	0.0212	0.1188	0.1835	0.036*	0.50

	U11	U22	U33	U12	U13	U23
Ni1	0.0199 (4)	0.0179 (4)	0.0259 (4)	0.000	0.0026 (3)	0.000
I1	0.03286 (18)	0.02414 (16)	0.0539 (2)	0.00044 (13)	0.01095 (15)	−0.00832 (15)
I2	0.02416 (17)	0.0449 (2)	0.0661 (3)	0.00048 (15)	0.01512 (16)	0.00269 (17)
N1	0.0261 (19)	0.0191 (19)	0.026 (2)	−0.0019 (15)	0.0007 (16)	0.0025 (15)
O1	0.0204 (15)	0.0220 (15)	0.0392 (19)	−0.0010 (12)	0.0072 (13)	−0.0029 (13)
C1	0.021 (2)	0.024 (2)	0.022 (2)	−0.0018 (18)	0.0026 (18)	0.0021 (18)
C2	0.023 (2)	0.024 (2)	0.025 (2)	0.0037 (18)	0.0038 (19)	−0.0022 (18)
C3	0.025 (2)	0.029 (2)	0.033 (3)	−0.007 (2)	0.003 (2)	−0.002 (2)
C4	0.019 (2)	0.034 (3)	0.034 (3)	0.002 (2)	0.0038 (19)	0.000 (2)
C5	0.024 (2)	0.025 (2)	0.033 (3)	0.0070 (19)	0.004 (2)	−0.0007 (19)
C6	0.021 (2)	0.022 (2)	0.027 (2)	0.0014 (18)	0.0023 (19)	−0.0017 (18)
C7	0.025 (2)	0.024 (2)	0.031 (3)	0.0064 (19)	0.001 (2)	0.0020 (19)
C8	0.032 (2)	0.025 (2)	0.030 (3)	0.000 (2)	0.000 (2)	0.0072 (19)
C9	0.036 (4)	0.021 (3)	0.033 (4)	0.000	0.005 (3)	0.000

Ni1—O1i	1.858 (3)	C3—H3	0.9300
Ni1—O1	1.858 (3)	C4—C5	1.365 (6)
Ni1—N1i	1.869 (3)	C5—C6	1.409 (6)
Ni1—N1	1.869 (3)	C5—H5	0.9300
I1—C2	2.098 (4)	C6—C7	1.440 (5)
I2—C4	2.096 (4)	C7—H7	0.9300
N1—C7	1.287 (5)	C8—C9	1.514 (5)
N1—C8	1.471 (5)	C8—H8A	0.9700
O1—C1	1.296 (5)	C8—H8B	0.9700
C1—C2	1.418 (5)	C9—C8i	1.514 (5)
C1—C6	1.421 (5)	C9—H9A	0.9700
C2—C3	1.369 (5)	C9—H9B	0.9700
C3—C4	1.391 (6)
O1i—Ni1—O1	84.57 (17)	C4—C5—C6	120.3 (4)
O1i—Ni1—N1i	92.01 (13)	C4—C5—H5	119.8
O1—Ni1—N1i	176.57 (13)	C6—C5—H5	119.8
O1i—Ni1—N1	176.57 (13)	C5—C6—C1	121.1 (4)
O1—Ni1—N1	92.01 (13)	C5—C6—C7	119.3 (4)
N1i—Ni1—N1	91.4 (2)	C1—C6—C7	118.9 (4)
C7—N1—C8	117.4 (3)	N1—C7—C6	125.6 (4)
C7—N1—Ni1	124.1 (3)	N1—C7—H7	117.2
C8—N1—Ni1	118.3 (3)	C6—C7—H7	117.2
C1—O1—Ni1	125.6 (3)	N1—C8—C9	113.2 (4)
O1—C1—C2	120.9 (4)	N1—C8—H8A	108.9
O1—C1—C6	123.7 (4)	C9—C8—H8A	108.9
C2—C1—C6	115.5 (4)	N1—C8—H8B	108.9
C3—C2—C1	122.9 (4)	C9—C8—H8B	108.9
C3—C2—I1	119.4 (3)	H8A—C8—H8B	107.7
C1—C2—I1	117.7 (3)	C8—C9—C8i	113.7 (5)
C2—C3—C4	119.8 (4)	C8—C9—H9A	108.8
C2—C3—H3	120.1	C8i—C9—H9A	108.8
C4—C3—H3	120.1	C8—C9—H9B	108.8
C5—C4—C3	120.2 (4)	C8i—C9—H9B	108.8
C5—C4—I2	118.9 (3)	H9A—C9—H9B	107.7
C3—C4—I2	120.8 (3)
N1i—Ni1—N1—C7	152.0 (4)	I2—C4—C5—C6	−178.8 (3)
N1i—Ni1—N1—C8	−31.8 (2)	C4—C5—C6—C1	0.4 (6)
O1i—Ni1—O1—C1	−148.9 (4)	C4—C5—C6—C7	−169.6 (4)
N1—Ni1—O1—C1	31.2 (3)	O1—C1—C6—C5	177.4 (4)
Ni1—O1—C1—C2	166.0 (3)	C2—C1—C6—C5	−4.4 (6)
Ni1—O1—C1—C6	−15.9 (6)	O1—C1—C6—C7	−12.5 (6)
O1—C1—C2—C3	−176.6 (4)	C2—C1—C6—C7	165.7 (4)
C6—C1—C2—C3	5.2 (6)	C8—N1—C7—C6	−166.2 (4)
O1—C1—C2—I1	4.6 (5)	Ni1—N1—C7—C6	10.0 (6)
C6—C1—C2—I1	−173.7 (3)	C5—C6—C7—N1	−174.2 (4)
C1—C2—C3—C4	−1.9 (7)	C1—C6—C7—N1	15.6 (7)
I1—C2—C3—C4	177.0 (3)	C7—N1—C8—C9	−116.1 (4)
C2—C3—C4—C5	−2.4 (7)	Ni1—N1—C8—C9	67.4 (4)
C2—C3—C4—I2	179.5 (3)	N1—C8—C9—C8i	−32.1 (2)
C3—C4—C5—C6	3.2 (7)