{4,4'-Dimethyl-2,2'-[(2,2-dimethyl-propane-1,3-di-yl)bis-(nitrilo-methanylyl-idene)]diphenolato}nickel(II) monohydrate.

In the title compound, [Ni(C(21)H(24)N(2)O(2))]·H(2)O, both the complex mol-ecule and the water mol-ecule lie on a twofold rotation axis. The Ni(II) ion is coordinated in a distorted square-planar geometry by the tetra-dentate ligand. The dihedral angle between the two symmetry-related benzene rings is 47.12 (8)°. In the crystal, pairs of symmetry-related O-H⋯O hydrogen bonds form R(2) (2)(6) ring motifs. In addition, there are weak inter-molecular C-H⋯O hydrogen bonds, and π-π stacking inter-actions with a centroid-centroid distance of 3.4760 (8) Å.

Related literature

For related structures, see for example: Fun et al. (2008 ▶); Kargar et al. (2008 ▶, 2011 ▶); Rayati et al. (2011 ▶); Kia et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Ni(C21H24N2O2)]·H2O

M = 413.15

Monoclinic,

a = 13.3333 (4) Å

b = 15.9424 (5) Å

c = 9.9965 (3) Å

β = 104.736 (1)°

V = 2055.01 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 296 K

0.25 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.794, T max = 0.927

17468 measured reflections

2557 independent reflections

2131 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.06

2557 reflections

125 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.31 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054262/lh5396sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054262/lh5396Isup2.hkl

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

[Ni(C21H24N2O2)]·H2O	F(000) = 872
Mr = 413.15	Dx = 1.335 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3245 reflections
a = 13.3333 (4) Å	θ = 2.8–27.8°
b = 15.9424 (5) Å	µ = 0.97 mm−1
c = 9.9965 (3) Å	T = 296 K
β = 104.736 (1)°	Block, red
V = 2055.01 (11) Å3	0.25 × 0.12 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2557 independent reflections
Radiation source: fine-focus sealed tube	2131 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→16
Tmin = 0.794, Tmax = 0.927	k = −21→21
17468 measured reflections	l = −13→13

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) = 0.083	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0485P)2] where P = (Fo2 + 2Fc2)/3
2557 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.31 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
Ni1	0.0000	0.489837 (15)	0.2500	0.03589 (11)
O1	0.09186 (9)	0.57316 (6)	0.34800 (11)	0.0457 (3)
N1	0.04523 (10)	0.40475 (8)	0.39178 (12)	0.0414 (3)
C1	0.16634 (12)	0.56212 (9)	0.46203 (15)	0.0401 (3)
C2	0.23779 (14)	0.62692 (10)	0.50786 (17)	0.0497 (4)
H2A	0.2346	0.6747	0.4537	0.060*
C3	0.31279 (14)	0.62162 (12)	0.63132 (18)	0.0567 (5)
H3A	0.3589	0.6660	0.6581	0.068*
C4	0.32147 (14)	0.55163 (13)	0.71719 (17)	0.0550 (4)
C5	0.25490 (14)	0.48675 (11)	0.67168 (18)	0.0487 (4)
H5A	0.2604	0.4390	0.7265	0.058*
C6	0.17758 (13)	0.48878 (9)	0.54427 (17)	0.0410 (3)
C7	0.40114 (17)	0.54821 (18)	0.85526 (19)	0.0817 (7)
H7A	0.4556	0.5101	0.8494	0.123*
H7B	0.3687	0.5292	0.9252	0.123*
H7C	0.4297	0.6031	0.8788	0.123*
C8	0.11388 (13)	0.41566 (10)	0.50691 (15)	0.0431 (4)
H8A	0.1230	0.3725	0.5714	0.052*
C9	−0.01669 (14)	0.32780 (10)	0.36982 (16)	0.0488 (4)
H9A	−0.0895	0.3426	0.3512	0.059*
H9B	0.0006	0.2949	0.4542	0.059*
C10	0.0000	0.27358 (15)	0.2500	0.0564 (7)
C11	0.0973 (2)	0.21930 (15)	0.2981 (2)	0.1038 (9)
H11A	0.1569	0.2548	0.3287	0.156*
H11B	0.1057	0.1851	0.2226	0.156*
H11C	0.0903	0.1840	0.3729	0.156*
O1W	0.0000	0.72531 (12)	0.2500	0.0992 (8)
H1	−0.0556	0.6878	0.2007	0.149*

	U11	U22	U33	U12	U13	U23
Ni1	0.03715 (18)	0.03024 (16)	0.03666 (16)	0.000	0.00274 (11)	0.000
O1	0.0462 (7)	0.0353 (6)	0.0472 (6)	−0.0002 (5)	−0.0032 (5)	0.0020 (5)
N1	0.0448 (8)	0.0367 (7)	0.0424 (7)	−0.0023 (6)	0.0110 (6)	0.0012 (5)
C1	0.0364 (8)	0.0408 (8)	0.0418 (8)	0.0035 (6)	0.0075 (6)	−0.0040 (6)
C2	0.0470 (10)	0.0449 (9)	0.0540 (9)	−0.0035 (7)	0.0069 (8)	−0.0022 (7)
C3	0.0434 (10)	0.0635 (12)	0.0586 (10)	−0.0101 (8)	0.0047 (8)	−0.0118 (9)
C4	0.0391 (10)	0.0794 (13)	0.0432 (9)	−0.0003 (9)	0.0042 (7)	−0.0047 (9)
C5	0.0428 (10)	0.0604 (11)	0.0413 (8)	0.0055 (8)	0.0076 (7)	0.0051 (7)
C6	0.0373 (9)	0.0449 (9)	0.0390 (8)	0.0040 (7)	0.0065 (7)	−0.0010 (6)
C7	0.0590 (14)	0.121 (2)	0.0537 (11)	−0.0122 (13)	−0.0074 (10)	−0.0005 (12)
C8	0.0472 (10)	0.0411 (8)	0.0408 (8)	0.0029 (7)	0.0109 (7)	0.0055 (6)
C9	0.0603 (11)	0.0394 (9)	0.0494 (9)	−0.0103 (8)	0.0189 (8)	0.0006 (7)
C10	0.0806 (19)	0.0355 (12)	0.0563 (14)	0.000	0.0236 (14)	0.000
C11	0.159 (3)	0.0726 (15)	0.0929 (16)	0.0629 (16)	0.0553 (17)	0.0332 (13)
O1W	0.1069 (18)	0.0426 (11)	0.1201 (18)	0.000	−0.0225 (15)	0.000

Ni1—O1	1.901 (1)	C5—H5A	0.9300
Ni1—O1i	1.9010 (10)	C6—C8	1.435 (2)
Ni1—N1i	1.9436 (12)	C7—H7A	0.9600
Ni1—N1	1.9436 (12)	C7—H7B	0.9600
O1—C1	1.3194 (17)	C7—H7C	0.9600
N1—C8	1.2870 (19)	C8—H8A	0.9300
N1—C9	1.4638 (19)	C9—C10	1.539 (2)
C1—C2	1.401 (2)	C9—H9A	0.9700
C1—C6	1.415 (2)	C9—H9B	0.9700
C2—C3	1.379 (2)	C10—C11	1.532 (2)
C2—H2A	0.9300	C10—C11i	1.532 (2)
C3—C4	1.394 (3)	C10—C9i	1.539 (2)
C3—H3A	0.9300	C11—H11A	0.9600
C4—C5	1.364 (3)	C11—H11B	0.9600
C4—C7	1.513 (2)	C11—H11C	0.9600
C5—C6	1.421 (2)	O1W—H1	0.9818
O1—Ni1—O1i	91.34 (6)	C4—C7—H7A	109.5
O1—Ni1—N1i	154.58 (6)	C4—C7—H7B	109.5
O1i—Ni1—N1i	94.14 (5)	H7A—C7—H7B	109.5
O1—Ni1—N1	94.14 (5)	C4—C7—H7C	109.5
O1i—Ni1—N1	154.58 (6)	H7A—C7—H7C	109.5
N1i—Ni1—N1	91.48 (7)	H7B—C7—H7C	109.5
C1—O1—Ni1	126.63 (9)	N1—C8—C6	125.58 (15)
C8—N1—C9	119.54 (13)	N1—C8—H8A	117.2
C8—N1—Ni1	125.16 (11)	C6—C8—H8A	117.2
C9—N1—Ni1	114.64 (10)	N1—C9—C10	113.57 (13)
O1—C1—C2	118.94 (14)	N1—C9—H9A	108.9
O1—C1—C6	123.87 (14)	C10—C9—H9A	108.9
C2—C1—C6	117.16 (15)	N1—C9—H9B	108.9
C3—C2—C1	121.69 (16)	C10—C9—H9B	108.9
C3—C2—H2A	119.2	H9A—C9—H9B	107.7
C1—C2—H2A	119.2	C11—C10—C11i	111.2 (3)
C2—C3—C4	121.84 (17)	C11—C10—C9i	106.43 (11)
C2—C3—H3A	119.1	C11i—C10—C9i	110.61 (11)
C4—C3—H3A	119.1	C11—C10—C9	110.61 (11)
C5—C4—C3	117.16 (16)	C11i—C10—C9	106.43 (11)
C5—C4—C7	121.55 (19)	C9i—C10—C9	111.63 (18)
C3—C4—C7	121.28 (19)	C10—C11—H11A	109.5
C4—C5—C6	122.98 (17)	C10—C11—H11B	109.5
C4—C5—H5A	118.5	H11A—C11—H11B	109.5
C6—C5—H5A	118.5	C10—C11—H11C	109.5
C1—C6—C5	119.02 (15)	H11A—C11—H11C	109.5
C1—C6—C8	123.49 (15)	H11B—C11—H11C	109.5
C5—C6—C8	117.48 (14)
O1i—Ni1—O1—C1	163.48 (15)	C7—C4—C5—C6	178.41 (17)
N1i—Ni1—O1—C1	−93.95 (16)	O1—C1—C6—C5	−174.24 (15)
N1—Ni1—O1—C1	8.32 (13)	C2—C1—C6—C5	4.2 (2)
O1—Ni1—N1—C8	1.34 (13)	O1—C1—C6—C8	5.0 (2)
O1i—Ni1—N1—C8	−100.61 (16)	C2—C1—C6—C8	−176.58 (15)
N1i—Ni1—N1—C8	156.53 (16)	C4—C5—C6—C1	−2.0 (3)
O1—Ni1—N1—C9	171.99 (11)	C4—C5—C6—C8	178.70 (16)
O1i—Ni1—N1—C9	70.04 (15)	C9—N1—C8—C6	−177.90 (15)
N1i—Ni1—N1—C9	−32.82 (8)	Ni1—N1—C8—C6	−7.7 (2)
Ni1—O1—C1—C2	169.47 (11)	C1—C6—C8—N1	5.6 (3)
Ni1—O1—C1—C6	−12.1 (2)	C5—C6—C8—N1	−175.14 (16)
O1—C1—C2—C3	175.28 (15)	C8—N1—C9—C10	−117.17 (16)
C6—C1—C2—C3	−3.2 (2)	Ni1—N1—C9—C10	71.61 (15)
C1—C2—C3—C4	−0.1 (3)	N1—C9—C10—C11	82.3 (2)
C2—C3—C4—C5	2.4 (3)	N1—C9—C10—C11i	−156.78 (16)
C2—C3—C4—C7	−177.33 (18)	N1—C9—C10—C9i	−36.00 (9)
C3—C4—C5—C6	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1ii	0.98	1.92	2.781 (2)	145
C3—H3A···O1Wiii	0.93	2.55	3.477 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O1i	0.98	1.92	2.781 (2)	145
C3—H3A⋯O1Wii	0.93	2.55	3.477 (2)	173

Symmetry codes: (i) ; (ii) .