{6,6′-Dimeth­oxy-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}nickel(II) 1.78-hydrate

Yeap, C.S.; Kia, R.; Kargar, H.; Fun, H.-K.

doi:10.1107/S1600536809014500

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m570-m571

doi:10.1107/S1600536809014500

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{6,6′-Dimethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenolato}nickel(II) 1.78-hydrate

Chin Sing Yeap,^a Reza Kia,^a ‡ Hadi Kargar ^b and Hoong-Kun Fun ^a ^*

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 16 April 2009; accepted 18 April 2009; online 25 April 2009)

In the title complex, [Ni(C₂₁H₂₄N₂O₄)]·1.78H₂O, the Ni^II ion has a slightly distorted planar geometry, coordinated by the two N and two O atoms of the tetradentate Schiff base ligand, with a mean deviation of 0.272 Å from the NiN₂O₂ plane. The N and O donor atoms are mutually cis. The dihedral angle between two benzene rings of the ligand is 38.86 (8)°. There are also three solvent water molecules, two of which lie across different crystallographic twofold rotation axes; one of these is partially occupied with a refined occupancy factor of 0.570 (7). The water molecules are linked together as tetramers in R₂²(8) ring motifs, which also connect two neighbouring molecules of the complex through a network of O—H⋯O hydrogen bonds. The crystal structure is further stabilized by intermolecular C—H⋯O and C—H⋯π interactions, which link neighbouring molecules into extended chains along the b axis. Other interesting features of the crystal structure are the short intermolecular C⋯C [3.204 (3)–3.365 (3) Å] and the C⋯O [3.199 (2)–3.205 (2) Å] contacts which are shorter than the sum of the van der Waals radii of these atoms.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Clark et al. (1968 , 1969 , 1970 ). For applications and bioactivity of Schiff base complexes, see: Elmali et al. (2000 ); Blower (1998 ); Granovski et al. (1993 ); Li & Chang (1991 ); Shahrokhian et al. (2000 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

[Ni(C₂₁H₂₄N₂O₄)]·1.78H₂O
M_r = 459.29
Monoclinic, C 2/c
a = 23.2513 (6) Å
b = 9.2709 (2) Å
c = 20.8024 (5) Å
β = 111.291 (1)°
V = 4178.12 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 100 K
0.48 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.655, T_max = 0.959
19991 measured reflections
6519 independent reflections
4609 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.098
S = 1.06
6519 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2Wⁱ	0.84	2.08	2.913 (2)	175
O2W—H1W2⋯O2	0.86	2.54	3.089 (2)	123
O2W—H1W2⋯O4	0.86	2.10	2.846 (2)	145
O2W—H2W2⋯O1	0.86	2.22	2.942 (2)	142
O2W—H2W2⋯O3	0.86	2.16	2.905 (2)	145
O3W—H1W3⋯O2Wⁱ	0.89	2.11	2.991 (3)	169
C10—H10B⋯O2ⁱⁱ	0.97	2.48	3.251 (2)	136
C8—H8B⋯Cg1ⁱⁱⁱ	0.97	2.57	3.370 (2)	139
C13—H13A⋯Cg1ⁱⁱ	0.93	2.75	3.377 (2)	125
Symmetry codes: (i) $[-x, y, -z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ . Cg1 is the centroid of the C1–C6 ring.

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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014500/sj2621sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014500/sj2621Isup2.hkl

checkCIF report

Comment top

Schiff base complexes are some of the most important stereochemical models in transition metal coordination chemistry, with their ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of Schiff bases have been studied extensively, and copper(II) and nickel(II) complexes play a major role in both synthetic and structural research (Elmali et al., 2000; Blower, 1998; Granovski et al., 1993; Li & Chang, 1991; Shahrokhian et al., 2000). Tetradentate Schiff base metal complexes may form trans or cis planar or tetrahedral structures (Elmali et al., 2000).

In the title compound (Fig. 1), the Ni^II ion shows a slightly distorted planar geometry which is coordinated by two imine N atoms and two phenol O atoms of the tetradentate Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with the related structures (Clark et al., 1968, 1969, 1970). The dihedral angle between two benzene rings is 38.84 (9)°.

Of the three solvent water molecules, two of them lie across different crystallographic twofold rotation axes and one of them is partially occupied with a refined occupancy factor of 0.570 (7). The water molecules are linked together as tetramers in R₂²(8) ring motifs which also connect two neighbouring molecules of the complex. The crystal structure is further stabilized by intermolecular C—H···O and C—H···π interactions (Table 1) which link neighbouring molecules into 1-dimensional extended chains along the b-axis (Fig. 2). Other interesting features of the crystal structure are the short intermolecular C1···C8ⁱⁱⁱ [3.204 (3) Å], C1···C11ⁱⁱ [3.364 (3) Å], C2···C8ⁱⁱⁱ [3.365 (3)], C7···O1ⁱⁱⁱ [3.199 (2) Å], and C11···O1ⁱⁱ [3.205 (2) Å] contacts (symmetry operations as in Table 1) which are shorter than the sum of the van der Waals radii of these atoms.

Related literature top

For bond-length data, see Allen et al. (1987). For related structures, see: Clark et al. (1968, 1969, 1970). For applications and bioactivity of Schiff base complexes, see: Elmali et al. (2000); Blower (1998); Granovski et al. (1993); Li & Chang (1991); Shahrokhian et al. (2000). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A chloroform solution (40 ml) of N,N'-ethylene-bis-(3-methoxy-2- hydroxysalicylaldimine) (1 mmol) was added to a methanol solution (20 ml) of NiCl₂.6H₂O (1.05 mmol, 237 mg). The mixture was refluxed for 30 min and then filtered. After keeping the filtrate in air, deep-green needle-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.

Computing details top

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

Figures top

	Fig. 1. The assymetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. The crystal packing of the title compound viewed down the b-axis, showing 1-dimensional extended chains along the b-axis. Intermolecular interactions are drawn as dashed lines.

{6,6'-Dimethoxy-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethylidyne)]diphenolato}nickel(II) 1.78-hydrate top

Crystal data top

[Ni(C₂₁H₂₄N₂O₄)]·1.78H₂O	F(000) = 1935
M_r = 459.29	D_x = 1.460 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5799 reflections
a = 23.2513 (6) Å	θ = 2.4–30.9°
b = 9.2709 (2) Å	µ = 0.97 mm⁻¹
c = 20.8024 (5) Å	T = 100 K
β = 111.291 (1)°	Needle, green
V = 4178.12 (17) Å³	0.48 × 0.06 × 0.04 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6519 independent reflections
Radiation source: fine-focus sealed tube	4609 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 30.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −33→30
T_min = 0.655, T_max = 0.959	k = −13→13
19991 measured reflections	l = −30→30

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0393P)² + 1.0555P] where P = (F_o² + 2F_c²)/3
6519 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ni(C₂₁H₂₄N₂O₄)]·1.78H₂O	V = 4178.12 (17) Å³
M_r = 459.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.2513 (6) Å	µ = 0.97 mm⁻¹
b = 9.2709 (2) Å	T = 100 K
c = 20.8024 (5) Å	0.48 × 0.06 × 0.04 mm
β = 111.291 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6519 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4609 reflections with I > 2σ(I)
T_min = 0.655, T_max = 0.959	R_int = 0.040
19991 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.06	Δρ_max = 0.56 e Å⁻³
6519 reflections	Δρ_min = −0.43 e Å⁻³
275 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.236534 (10)	0.03020 (3)	0.016967 (11)	0.01197 (8)
O1	0.20185 (6)	−0.04173 (15)	−0.07256 (6)	0.0141 (3)
O2	0.15706 (6)	0.08978 (16)	0.00363 (6)	0.0146 (3)
O3	0.15150 (6)	−0.03871 (16)	−0.20732 (7)	0.0198 (3)
O4	0.03874 (6)	0.13066 (18)	−0.03278 (7)	0.0263 (4)
N1	0.30718 (7)	−0.08539 (19)	0.04015 (7)	0.0126 (3)
N2	0.27481 (7)	0.15663 (19)	0.09066 (7)	0.0131 (3)
C1	0.23268 (8)	−0.1077 (2)	−0.10589 (9)	0.0128 (4)
C2	0.20584 (8)	−0.1127 (2)	−0.17960 (9)	0.0143 (4)
C3	0.23389 (9)	−0.1867 (2)	−0.21739 (10)	0.0184 (4)
H3A	0.2162	−0.1864	−0.2653	0.022*
C4	0.28894 (9)	−0.2625 (3)	−0.18454 (10)	0.0215 (5)
H4A	0.3070	−0.3147	−0.2104	0.026*
C5	0.31593 (9)	−0.2592 (2)	−0.11392 (10)	0.0191 (5)
H5A	0.3520	−0.3111	−0.0920	0.023*
C6	0.28970 (8)	−0.1783 (2)	−0.07416 (9)	0.0139 (4)
C7	0.32108 (8)	−0.1720 (2)	−0.00063 (9)	0.0149 (4)
H7A	0.3539	−0.2351	0.0191	0.018*
C8	0.34214 (8)	−0.0980 (2)	0.11514 (9)	0.0143 (4)
H8A	0.3701	−0.1794	0.1235	0.017*
H8B	0.3135	−0.1169	0.1384	0.017*
C9	0.37932 (8)	0.0387 (2)	0.14565 (9)	0.0145 (4)
C10	0.34240 (8)	0.1725 (2)	0.11110 (9)	0.0151 (4)
H10A	0.3559	0.2534	0.1426	0.018*
H10B	0.3517	0.1951	0.0704	0.018*
C11	0.24663 (8)	0.2501 (2)	0.11465 (9)	0.0136 (4)
H11A	0.2713	0.3124	0.1484	0.016*
C12	0.18108 (8)	0.2677 (2)	0.09453 (9)	0.0137 (4)
C13	0.15822 (9)	0.3744 (2)	0.12736 (9)	0.0165 (4)
H13A	0.1857	0.4290	0.1627	0.020*
C14	0.09596 (9)	0.3987 (2)	0.10780 (10)	0.0185 (4)
H14A	0.0815	0.4692	0.1299	0.022*
C15	0.05432 (9)	0.3170 (2)	0.05440 (10)	0.0197 (5)
H15A	0.0121	0.3326	0.0415	0.024*
C16	0.07557 (9)	0.2138 (2)	0.02094 (10)	0.0176 (4)
C17	0.14009 (8)	0.1858 (2)	0.03968 (9)	0.0140 (4)
C18	0.44051 (8)	0.0392 (3)	0.13346 (11)	0.0207 (5)
H18A	0.4323	0.0397	0.0848	0.031*
H18B	0.4638	−0.0454	0.1538	0.031*
H18C	0.4637	0.1237	0.1542	0.031*
C19	0.39200 (9)	0.0387 (3)	0.22342 (10)	0.0212 (5)
H19A	0.4149	0.1235	0.2440	0.032*
H19B	0.4155	−0.0455	0.2441	0.032*
H19C	0.3535	0.0379	0.2307	0.032*
C20	0.11522 (10)	−0.0671 (3)	−0.27807 (10)	0.0265 (5)
H20A	0.0770	−0.0152	−0.2908	0.040*
H20B	0.1069	−0.1686	−0.2843	0.040*
H20C	0.1374	−0.0365	−0.3066	0.040*
C21	−0.02618 (9)	0.1585 (3)	−0.05688 (11)	0.0341 (6)
H21A	−0.0470	0.0964	−0.0952	0.051*
H21B	−0.0338	0.2573	−0.0712	0.051*
H21C	−0.0413	0.1404	−0.0204	0.051*
O1W	0.0000	0.1551 (3)	−0.2500	0.0449 (7)
H1W1	−0.0179	0.1045	−0.2849	0.067*
O2W	0.06628 (7)	−0.03162 (18)	−0.13412 (8)	0.0316 (4)
H1W2	0.0657	−0.0153	−0.0937	0.047*
H2W2	0.1022	−0.0323	−0.1371	0.047*
O3W	0.0000	−0.2322 (4)	−0.2500	0.0320 (14)	0.570 (7)
H1W3	−0.0239	−0.1811	−0.2860	0.048*	0.570 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01173 (11)	0.01265 (14)	0.01018 (11)	0.00058 (11)	0.00237 (8)	−0.00026 (11)
O1	0.0139 (6)	0.0158 (8)	0.0120 (6)	0.0011 (6)	0.0038 (5)	−0.0010 (6)
O2	0.0139 (6)	0.0159 (8)	0.0136 (6)	0.0012 (6)	0.0046 (5)	−0.0023 (6)
O3	0.0219 (7)	0.0210 (9)	0.0112 (6)	0.0054 (7)	−0.0001 (5)	−0.0023 (6)
O4	0.0119 (6)	0.0375 (10)	0.0256 (7)	0.0012 (7)	0.0020 (6)	−0.0132 (8)
N1	0.0132 (7)	0.0132 (9)	0.0104 (7)	−0.0018 (7)	0.0029 (6)	0.0011 (7)
N2	0.0137 (7)	0.0136 (9)	0.0105 (7)	−0.0004 (7)	0.0026 (6)	0.0029 (7)
C1	0.0146 (8)	0.0109 (10)	0.0133 (8)	−0.0031 (8)	0.0057 (7)	0.0002 (8)
C2	0.0155 (8)	0.0113 (11)	0.0150 (8)	−0.0020 (8)	0.0042 (7)	0.0000 (8)
C3	0.0231 (10)	0.0193 (12)	0.0135 (9)	−0.0021 (9)	0.0073 (8)	−0.0020 (9)
C4	0.0229 (10)	0.0242 (13)	0.0209 (10)	−0.0005 (10)	0.0123 (8)	−0.0073 (10)
C5	0.0144 (9)	0.0224 (13)	0.0210 (10)	0.0031 (9)	0.0070 (8)	−0.0004 (10)
C6	0.0142 (8)	0.0127 (10)	0.0150 (8)	−0.0030 (8)	0.0055 (7)	−0.0010 (8)
C7	0.0120 (8)	0.0144 (11)	0.0173 (9)	−0.0009 (8)	0.0042 (7)	0.0008 (9)
C8	0.0145 (8)	0.0146 (11)	0.0116 (8)	0.0000 (8)	0.0023 (7)	0.0028 (8)
C9	0.0140 (8)	0.0145 (11)	0.0132 (8)	−0.0025 (8)	0.0029 (7)	0.0002 (8)
C10	0.0146 (8)	0.0150 (11)	0.0161 (9)	−0.0028 (8)	0.0059 (7)	0.0012 (9)
C11	0.0183 (9)	0.0116 (11)	0.0101 (8)	−0.0026 (8)	0.0044 (7)	0.0020 (8)
C12	0.0175 (9)	0.0120 (11)	0.0129 (8)	0.0001 (8)	0.0071 (7)	0.0030 (8)
C13	0.0226 (9)	0.0129 (11)	0.0149 (9)	−0.0025 (9)	0.0078 (7)	0.0007 (8)
C14	0.0240 (10)	0.0166 (12)	0.0174 (9)	0.0038 (9)	0.0104 (8)	0.0009 (9)
C15	0.0156 (9)	0.0258 (13)	0.0188 (9)	0.0040 (9)	0.0076 (7)	0.0013 (10)
C16	0.0169 (9)	0.0205 (12)	0.0142 (9)	0.0008 (9)	0.0043 (7)	0.0004 (9)
C17	0.0164 (8)	0.0131 (11)	0.0131 (8)	0.0020 (8)	0.0061 (7)	0.0043 (8)
C18	0.0137 (8)	0.0220 (12)	0.0249 (10)	−0.0019 (9)	0.0052 (8)	0.0020 (10)
C19	0.0222 (10)	0.0235 (13)	0.0149 (9)	−0.0025 (10)	0.0033 (7)	−0.0007 (9)
C20	0.0263 (11)	0.0322 (15)	0.0139 (9)	0.0054 (11)	−0.0012 (8)	−0.0034 (10)
C21	0.0135 (9)	0.0545 (18)	0.0291 (11)	0.0012 (11)	0.0016 (8)	−0.0149 (13)
O1W	0.0409 (14)	0.0342 (16)	0.0516 (16)	0.000	0.0072 (12)	0.000
O2W	0.0210 (7)	0.0427 (11)	0.0294 (8)	−0.0017 (8)	0.0073 (6)	−0.0150 (8)
O3W	0.031 (2)	0.023 (3)	0.038 (2)	0.000	0.0070 (18)	0.000

Geometric parameters (Å, º) top

Ni1—O2	1.8505 (13)	C9—C19	1.535 (3)
Ni1—O1	1.8636 (13)	C10—H10A	0.9700
Ni1—N1	1.8719 (16)	C10—H10B	0.9700
Ni1—N2	1.8776 (16)	C11—C12	1.436 (2)
O1—C1	1.315 (2)	C11—H11A	0.9300
O2—C17	1.313 (2)	C12—C13	1.411 (3)
O3—C2	1.368 (2)	C12—C17	1.413 (3)
O3—C20	1.430 (2)	C13—C14	1.373 (3)
O4—C16	1.372 (2)	C13—H13A	0.9300
O4—C21	1.431 (2)	C14—C15	1.402 (3)
N1—C7	1.292 (2)	C14—H14A	0.9300
N1—C8	1.479 (2)	C15—C16	1.376 (3)
N2—C11	1.291 (2)	C15—H15A	0.9300
N2—C10	1.479 (2)	C16—C17	1.430 (2)
C1—C6	1.409 (3)	C18—H18A	0.9600
C1—C2	1.431 (2)	C18—H18B	0.9600
C2—C3	1.373 (3)	C18—H18C	0.9600
C3—C4	1.402 (3)	C19—H19A	0.9600
C3—H3A	0.9300	C19—H19B	0.9600
C4—C5	1.372 (3)	C19—H19C	0.9600
C4—H4A	0.9300	C20—H20A	0.9600
C5—C6	1.409 (3)	C20—H20B	0.9600
C5—H5A	0.9300	C20—H20C	0.9600
C6—C7	1.437 (2)	C21—H21A	0.9600
C7—H7A	0.9300	C21—H21B	0.9600
C8—C9	1.536 (3)	C21—H21C	0.9600
C8—H8A	0.9700	O1W—H1W1	0.8368
C8—H8B	0.9700	O2W—H1W2	0.8598
C9—C10	1.531 (3)	O2W—H2W2	0.8602
C9—C18	1.533 (3)	O3W—H1W3	0.8900

O2—Ni1—O1	84.88 (5)	C9—C10—H10A	108.7
O2—Ni1—N1	160.84 (7)	N2—C10—H10B	108.7
O1—Ni1—N1	94.21 (6)	C9—C10—H10B	108.7
O2—Ni1—N2	95.02 (6)	H10A—C10—H10B	107.6
O1—Ni1—N2	160.77 (7)	N2—C11—C12	126.70 (18)
N1—Ni1—N2	92.04 (7)	N2—C11—H11A	116.7
C1—O1—Ni1	124.91 (11)	C12—C11—H11A	116.7
C17—O2—Ni1	127.39 (12)	C13—C12—C17	120.35 (17)
C2—O3—C20	116.80 (15)	C13—C12—C11	119.01 (18)
C16—O4—C21	116.83 (17)	C17—C12—C11	120.51 (17)
C7—N1—C8	118.09 (16)	C14—C13—C12	120.92 (18)
C7—N1—Ni1	126.32 (13)	C14—C13—H13A	119.5
C8—N1—Ni1	114.32 (12)	C12—C13—H13A	119.5
C11—N2—C10	117.23 (16)	C13—C14—C15	119.78 (19)
C11—N2—Ni1	125.31 (13)	C13—C14—H14A	120.1
C10—N2—Ni1	115.85 (12)	C15—C14—H14A	120.1
O1—C1—C6	124.71 (16)	C16—C15—C14	120.34 (18)
O1—C1—C2	118.08 (16)	C16—C15—H15A	119.8
C6—C1—C2	117.18 (17)	C14—C15—H15A	119.8
O3—C2—C3	124.56 (17)	O4—C16—C15	124.75 (17)
O3—C2—C1	114.34 (16)	O4—C16—C17	113.76 (17)
C3—C2—C1	121.10 (18)	C15—C16—C17	121.48 (18)
C2—C3—C4	120.73 (18)	O2—C17—C12	124.81 (17)
C2—C3—H3A	119.6	O2—C17—C16	118.05 (17)
C4—C3—H3A	119.6	C12—C17—C16	117.11 (18)
C5—C4—C3	119.49 (18)	C9—C18—H18A	109.5
C5—C4—H4A	120.3	C9—C18—H18B	109.5
C3—C4—H4A	120.3	H18A—C18—H18B	109.5
C4—C5—C6	120.88 (18)	C9—C18—H18C	109.5
C4—C5—H5A	119.6	H18A—C18—H18C	109.5
C6—C5—H5A	119.6	H18B—C18—H18C	109.5
C5—C6—C1	120.43 (17)	C9—C19—H19A	109.5
C5—C6—C7	119.07 (17)	C9—C19—H19B	109.5
C1—C6—C7	120.48 (17)	H19A—C19—H19B	109.5
N1—C7—C6	124.96 (18)	C9—C19—H19C	109.5
N1—C7—H7A	117.5	H19A—C19—H19C	109.5
C6—C7—H7A	117.5	H19B—C19—H19C	109.5
N1—C8—C9	112.44 (16)	O3—C20—H20A	109.5
N1—C8—H8A	109.1	O3—C20—H20B	109.5
C9—C8—H8A	109.1	H20A—C20—H20B	109.5
N1—C8—H8B	109.1	O3—C20—H20C	109.5
C9—C8—H8B	109.1	H20A—C20—H20C	109.5
H8A—C8—H8B	107.8	H20B—C20—H20C	109.5
C10—C9—C18	108.41 (16)	O4—C21—H21A	109.5
C10—C9—C19	110.81 (16)	O4—C21—H21B	109.5
C18—C9—C19	109.85 (15)	H21A—C21—H21B	109.5
C10—C9—C8	109.82 (15)	O4—C21—H21C	109.5
C18—C9—C8	110.55 (17)	H21A—C21—H21C	109.5
C19—C9—C8	107.40 (16)	H21B—C21—H21C	109.5
N2—C10—C9	114.23 (16)	H1W2—O2W—H2W2	115.6
N2—C10—H10A	108.7

O2—Ni1—O1—C1	179.08 (15)	C8—N1—C7—C6	176.88 (17)
N1—Ni1—O1—C1	−20.13 (16)	Ni1—N1—C7—C6	10.6 (3)
N2—Ni1—O1—C1	88.5 (2)	C5—C6—C7—N1	168.97 (19)
O1—Ni1—O2—C17	−162.95 (16)	C1—C6—C7—N1	−12.7 (3)
N1—Ni1—O2—C17	109.0 (2)	C7—N1—C8—C9	116.78 (19)
N2—Ni1—O2—C17	−2.25 (16)	Ni1—N1—C8—C9	−75.31 (16)
O2—Ni1—N1—C7	90.5 (2)	N1—C8—C9—C10	37.6 (2)
O1—Ni1—N1—C7	3.93 (17)	N1—C8—C9—C18	−81.95 (19)
N2—Ni1—N1—C7	−157.87 (17)	N1—C8—C9—C19	158.22 (15)
O2—Ni1—N1—C8	−76.3 (2)	C11—N2—C10—C9	123.82 (18)
O1—Ni1—N1—C8	−162.81 (13)	Ni1—N2—C10—C9	−69.85 (17)
N2—Ni1—N1—C8	35.38 (13)	C18—C9—C10—N2	153.78 (16)
O2—Ni1—N2—C11	−2.15 (16)	C19—C9—C10—N2	−85.59 (19)
O1—Ni1—N2—C11	86.7 (2)	C8—C9—C10—N2	32.9 (2)
N1—Ni1—N2—C11	−164.32 (16)	C10—N2—C11—C12	170.83 (17)
O2—Ni1—N2—C10	−167.23 (13)	Ni1—N2—C11—C12	5.9 (3)
O1—Ni1—N2—C10	−78.4 (2)	N2—C11—C12—C13	178.81 (18)
N1—Ni1—N2—C10	30.60 (13)	N2—C11—C12—C17	−5.2 (3)
Ni1—O1—C1—C6	23.2 (3)	C17—C12—C13—C14	1.4 (3)
Ni1—O1—C1—C2	−158.92 (14)	C11—C12—C13—C14	177.37 (18)
C20—O3—C2—C3	14.6 (3)	C12—C13—C14—C15	−0.2 (3)
C20—O3—C2—C1	−165.57 (18)	C13—C14—C15—C16	−0.8 (3)
O1—C1—C2—O3	3.8 (3)	C21—O4—C16—C15	2.5 (3)
C6—C1—C2—O3	−178.18 (17)	C21—O4—C16—C17	−176.59 (19)
O1—C1—C2—C3	−176.36 (18)	C14—C15—C16—O4	−178.51 (19)
C6—C1—C2—C3	1.7 (3)	C14—C15—C16—C17	0.6 (3)
O3—C2—C3—C4	−178.48 (19)	Ni1—O2—C17—C12	3.2 (3)
C1—C2—C3—C4	1.6 (3)	Ni1—O2—C17—C16	−178.97 (13)
C2—C3—C4—C5	−1.9 (3)	C13—C12—C17—O2	176.22 (18)
C3—C4—C5—C6	−1.3 (3)	C11—C12—C17—O2	0.3 (3)
C4—C5—C6—C1	4.7 (3)	C13—C12—C17—C16	−1.6 (3)
C4—C5—C6—C7	−176.9 (2)	C11—C12—C17—C16	−177.50 (18)
O1—C1—C6—C5	173.11 (18)	O4—C16—C17—O2	1.8 (3)
C2—C1—C6—C5	−4.8 (3)	C15—C16—C17—O2	−177.33 (18)
O1—C1—C6—C7	−5.2 (3)	O4—C16—C17—C12	179.80 (17)
C2—C1—C6—C7	176.85 (18)	C15—C16—C17—C12	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2Wⁱ	0.84	2.08	2.913 (2)	175
O2W—H1W2···O2	0.86	2.54	3.089 (2)	123
O2W—H1W2···O4	0.86	2.10	2.846 (2)	145
O2W—H2W2···O1	0.86	2.22	2.942 (2)	142
O2W—H2W2···O3	0.86	2.16	2.905 (2)	145
O3W—H1W3···O2Wⁱ	0.89	2.11	2.991 (3)	169
C10—H10B···O2ⁱⁱ	0.97	2.48	3.251 (2)	136
C8—H8B···Cg1ⁱⁱⁱ	0.97	2.57	3.370 (2)	139
C13—H13A···Cg1ⁱⁱ	0.93	2.75	3.377 (2)	125

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂₁H₂₄N₂O₄)]·1.78H₂O
M_r	459.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	23.2513 (6), 9.2709 (2), 20.8024 (5)
β (°)	111.291 (1)
V (Å³)	4178.12 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.48 × 0.06 × 0.04

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.655, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	19991, 6519, 4609
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.723

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.098, 1.06
No. of reflections	6519
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.43

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2Wⁱ	0.8400	2.0800	2.913 (2)	175.00
O2W—H1W2···O2	0.8600	2.5400	3.089 (2)	123.00
O2W—H1W2···O4	0.8600	2.1000	2.846 (2)	145.00
O2W—H2W2···O1	0.8600	2.2200	2.942 (2)	142.00
O2W—H2W2···O3	0.8600	2.1600	2.905 (2)	145.00
O3W—H1W3···O2Wⁱ	0.8900	2.1100	2.991 (3)	169.00
C10—H10B···O2ⁱⁱ	0.9700	2.4800	3.251 (2)	136.00
C8—H8B···Cg1ⁱⁱⁱ	0.9700	2.5700	3.370 (2)	139.00
C13—H13A···Cg1ⁱⁱ	0.9300	2.7500	3.377 (2)	125.00

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

Footnotes

‡Additional correspondence author, e-mail: zsrkk@yahoo.com.

Acknowledgements

HKF, RK and CSY thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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Volume 65| Part 5| May 2009| Pages m570-m571

doi:10.1107/S1600536809014500

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{6,6′-Dimeth­­oxy-2,2′-[2,2-di­methyl­propane-1,3-diylbis(nitrilo­methyl­­idyne)]diphenolato}nickel(II) 1.78-hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

metal-organic compounds

{6,6′-Dimethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenolato}nickel(II) 1.78-hydrate