{6,6′-Dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato}nickel(II) dimethyl­formamide monosolvate

Ayikoé, K.; Butcher, R.J.; Gultneh, Y.

doi:10.1107/S1600536811004818

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m328

doi:10.1107/S1600536811004818

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{6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}nickel(II) dimethylformamide monosolvate

Kouassi Ayikoé,^a Ray J. Butcher ^a ^* and Yilma Gultneh ^a

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 31 January 2011; accepted 8 February 2011; online 12 February 2011)

In the title compound, [Ni(C₁₈H₁₈N₂O₄)]·C₃H₇NO, the central Ni^II atom is in a square-planar O₂N₂ coordination environment. The planar Ni–salen moieties (r.m.s. deviation for the plane through the conjugated part of the Ni–salen group = 0.07 Å) form parallel stacks in the a-axis direction, with alternating Ni⋯Ni separations of 3.5339 (7) and 3.6165 (7) Å. In the crystal, there are weak intermolecular C—H⋯O interactions involving the dimethylformamide O and phenolate O atoms.

Related literature

For stacking of Ni–salen units, see: Abe et al. (2006 ); Assey et al. (2010 ); Feng et al. (2007 ); Miyamura et al. (1995 ); Vasil'eva et al. (2003 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

[Ni(C₁₈H₁₈N₂O₄)]·C₃H₇NO
M_r = 458.15
Monoclinic, P 2₁ /c
a = 6.8601 (1) Å
b = 15.3432 (3) Å
c = 18.9065 (4) Å
β = 91.676 (2)°
V = 1989.17 (6) Å³
Z = 4
Cu Kα radiation
μ = 1.75 mm⁻¹
T = 110 K
0.53 × 0.35 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.750, T_max = 1.000
7909 measured reflections
3911 independent reflections
3513 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.10
3911 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni—N1	1.8503 (17)
Ni—N2	1.8502 (17)
Ni—O1	1.8609 (13)
Ni—O2	1.8594 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1S	0.95	2.62	3.310 (3)	130
C9—H9A⋯O2ⁱ	0.99	2.45	3.334 (3)	148
C10—H10A⋯O1ⁱⁱ	0.99	2.45	3.348 (3)	151
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004818/tk2717sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004818/tk2717Isup2.hkl

checkCIF report

Comment top

The title compound is a composed of one mononuclear nickel salen-type complex and one molecule of dimethylformamide as solvate. The central Ni is in a square planar O₂N₂ coordination environment (Fig. 1). The Ni—N and Ni—O bond distances, Table 1, are in the normal range for Ni-salen type complexes (Allen, 2002). The planar Ni salen moieties form parallel stacks in the a direction with alternating Ni—Ni separations of 3.5339 (7) and 3.6165 (7) Å as is common for this type of complex (Abe et al., 2006; Assey et al., 2010; Feng et al., 2007; Miyamura et al., 1995; Vasil'eva et al., 2003). There are weak intermolecular C—H···O interactions involving the DMF O and phenolic O atoms (Table 2 and Fig. 2).

Related literature top

For stacking of Ni–salen units, see: Abe et al. (2006); Assey et al. (2010); Feng et al. (2007); Miyamura et al. (1995); Vasil'eva et al. (2003). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The ligand, N,N'-bis(3-methoxysalicylaldehyde)ethylenediimine (H₂L₁), was synthesized in a conventional way by mixing o-vanillin with ethylenediamine. To 10 g (0.066 mole) of o-vanillin weighed into a 100 ml round-bottom flask, 30 ml of methanol and 3 mL (0.035 mole) of ethylenediamine were added drop-wise while stirring. The resulting mixture was refluxed at a regulated temperature of 313 K overnight. The yellow precipitate was filtered under vacuum, dissolved in methanol and filtered a second time.

To a stirred bright yellow solution of 20 ml methanol containing 0.9 g (2.74 mmol) of H₂L₁, a 20 ml green methanol solution of 0.65 g NiCl₂.6H₂O (2.73 mmol) was added drop-wise with continuous stirring. About 2 to 3 drops of triethylamine was added to activate deprotonation of the 2-hydroxyl group on the aldehyde moiety and promote oxygen binding to the metal. The resulting dark brown complex solution was stirred and refluxed overnight at 313 K, rotary-evaporated and washed with ethanol to obtain a brown solid in over 90% yield. The complex (7 mg) was dissolved in 5 ml of N,N'-dimethyl formamide and filtered into a crystallization tube. Sufficient amount of diethyl ether was slowly layered over the dissolved complex yielding red brown crystals after several days.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structures of the complex, C₁₈H₁₈N₃NiO₅, and solvent, C₃H₇NO, showing the atom numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. The molecular packing for C₁₈H₁₈N₃NiO₅.C₃H₇NO, viewed down the a axis showing overlapping Nisalen units.

{6,6'-Dimethoxy-2,2'-[ethane-1,2- diylbis(nitrilomethanylylidene)]diphenolato}nickel(II) dimethylformamide monosolvate top

Crystal data top

[Ni(C₁₈H₁₈N₂O₄)]·C₃H₇NO	F(000) = 960
M_r = 458.15	D_x = 1.530 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 5823 reflections
a = 6.8601 (1) Å	θ = 5.5–73.9°
b = 15.3432 (3) Å	µ = 1.75 mm⁻¹
c = 18.9065 (4) Å	T = 110 K
β = 91.676 (2)°	Prism, red brown
V = 1989.17 (6) Å³	0.53 × 0.35 × 0.28 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector	3911 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3513 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.1°, θ_min = 5.5°
ω scans	h = −8→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −18→18
T_min = 0.750, T_max = 1.000	l = −22→23
7909 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0443P)² + 2.5615P] where P = (F_o² + 2F_c²)/3
3911 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Ni(C₁₈H₁₈N₂O₄)]·C₃H₇NO	V = 1989.17 (6) Å³
M_r = 458.15	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 6.8601 (1) Å	µ = 1.75 mm⁻¹
b = 15.3432 (3) Å	T = 110 K
c = 18.9065 (4) Å	0.53 × 0.35 × 0.28 mm
β = 91.676 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector	3911 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3513 reflections with I > 2σ(I)
T_min = 0.750, T_max = 1.000	R_int = 0.020
7909 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.10	Δρ_max = 0.34 e Å⁻³
3911 reflections	Δρ_min = −0.31 e Å⁻³
275 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ni	0.74901 (5)	0.498467 (19)	0.526650 (16)	0.01230 (13)
O1	0.7304 (2)	0.41708 (9)	0.59911 (7)	0.0156 (3)
O2	0.7642 (2)	0.58041 (9)	0.59906 (7)	0.0153 (3)
O3	0.7206 (2)	0.32568 (9)	0.71759 (7)	0.0202 (3)
O4	0.7569 (2)	0.67226 (9)	0.71712 (7)	0.0219 (3)
O1S	0.5907 (2)	−0.00040 (9)	0.71449 (9)	0.0270 (4)
N1	0.7406 (2)	0.41614 (11)	0.45511 (9)	0.0159 (3)
N2	0.7631 (2)	0.57987 (11)	0.45478 (9)	0.0160 (3)
N1S	0.2629 (3)	−0.00026 (10)	0.69058 (10)	0.0191 (4)
C1	0.7385 (3)	0.33191 (13)	0.59320 (10)	0.0143 (4)
C2	0.7330 (3)	0.27939 (13)	0.65578 (10)	0.0159 (4)
C3	0.7344 (3)	0.27729 (14)	0.78197 (11)	0.0214 (4)
H3A	0.7272	0.3173	0.8222	0.032*
H3B	0.8588	0.2459	0.7845	0.032*
H3C	0.6266	0.2355	0.7834	0.032*
C4	0.7376 (3)	0.18962 (13)	0.65251 (11)	0.0198 (4)
H4A	0.7304	0.1564	0.6948	0.024*
C5	0.7531 (3)	0.14675 (13)	0.58720 (12)	0.0257 (5)
H5A	0.7577	0.0849	0.5853	0.031*
C6	0.7613 (3)	0.19459 (15)	0.52644 (12)	0.0251 (5)
H6A	0.7735	0.1657	0.4823	0.030*
C7	0.7518 (3)	0.28656 (14)	0.52840 (11)	0.0191 (4)
C8	0.7480 (3)	0.33263 (14)	0.46263 (11)	0.0194 (4)
H8A	0.7513	0.2987	0.4207	0.023*
C9	0.7123 (3)	0.45208 (15)	0.38295 (10)	0.0219 (4)
H9A	0.5720	0.4523	0.3692	0.026*
H9B	0.7824	0.4159	0.3486	0.026*
C10	0.7908 (3)	0.54324 (14)	0.38323 (10)	0.0215 (4)
H10A	0.9310	0.5429	0.3722	0.026*
H10B	0.7202	0.5789	0.3472	0.026*
C11	0.7590 (3)	0.66365 (14)	0.46181 (11)	0.0195 (4)
H11A	0.7622	0.6974	0.4197	0.023*
C12	0.7500 (3)	0.71005 (14)	0.52714 (11)	0.0192 (4)
C13	0.7388 (3)	0.80217 (15)	0.52450 (12)	0.0252 (5)
H13A	0.7355	0.8308	0.4799	0.030*
C14	0.7328 (3)	0.85024 (14)	0.58504 (13)	0.0268 (5)
H14A	0.7254	0.9120	0.5827	0.032*
C15	0.7376 (3)	0.80773 (13)	0.65102 (12)	0.0203 (4)
H15A	0.7318	0.8411	0.6933	0.024*
C16	0.7506 (3)	0.71821 (13)	0.65496 (10)	0.0164 (4)
C17	0.7597 (3)	0.72153 (15)	0.78123 (11)	0.0220 (4)
H17A	0.7687	0.6818	0.8218	0.033*
H17B	0.6397	0.7559	0.7836	0.033*
H17C	0.8726	0.7607	0.7823	0.033*
C18	0.7554 (3)	0.66541 (13)	0.59253 (10)	0.0146 (4)
C1S	0.4214 (3)	−0.00156 (11)	0.73382 (12)	0.0181 (4)
H1SA	0.4011	−0.0035	0.7833	0.022*
C2S	0.0692 (3)	−0.00288 (14)	0.71929 (14)	0.0270 (5)
H2SA	0.0795	−0.0017	0.7711	0.040*
H2SB	0.0029	−0.0564	0.7038	0.040*
H2SC	−0.0057	0.0478	0.7024	0.040*
C3S	0.2806 (5)	0.00255 (16)	0.61430 (13)	0.0347 (6)
H3SA	0.4173	0.0120	0.6028	0.052*
H3SB	0.2009	0.0503	0.5948	0.052*
H3SC	0.2355	−0.0528	0.5938	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.0174 (2)	0.0113 (2)	0.00815 (19)	−0.00089 (12)	0.00040 (13)	0.00026 (11)
O1	0.0232 (7)	0.0109 (6)	0.0127 (6)	−0.0014 (5)	0.0010 (5)	0.0000 (5)
O2	0.0216 (7)	0.0113 (6)	0.0131 (6)	−0.0013 (5)	0.0005 (5)	−0.0001 (5)
O3	0.0333 (8)	0.0145 (7)	0.0130 (7)	0.0003 (6)	0.0024 (6)	0.0026 (5)
O4	0.0373 (9)	0.0150 (7)	0.0135 (7)	−0.0009 (6)	0.0018 (6)	−0.0027 (5)
O1S	0.0217 (8)	0.0249 (9)	0.0347 (9)	0.0000 (6)	0.0039 (7)	0.0014 (6)
N1	0.0175 (8)	0.0195 (9)	0.0105 (8)	−0.0004 (7)	−0.0001 (6)	−0.0017 (6)
N2	0.0169 (8)	0.0201 (9)	0.0110 (8)	−0.0018 (6)	−0.0002 (6)	0.0023 (6)
N1S	0.0239 (9)	0.0172 (9)	0.0162 (9)	−0.0004 (7)	−0.0001 (7)	0.0003 (6)
C1	0.0135 (9)	0.0121 (9)	0.0173 (9)	−0.0003 (7)	0.0005 (7)	−0.0002 (7)
C2	0.0140 (9)	0.0163 (10)	0.0176 (9)	−0.0002 (7)	0.0012 (7)	0.0000 (7)
C3	0.0244 (11)	0.0227 (10)	0.0171 (10)	−0.0001 (8)	0.0008 (8)	0.0067 (8)
C4	0.0203 (10)	0.0152 (10)	0.0238 (11)	−0.0002 (8)	−0.0001 (8)	0.0035 (8)
C5	0.0328 (12)	0.0108 (9)	0.0334 (13)	−0.0007 (8)	−0.0017 (10)	−0.0022 (8)
C6	0.0339 (12)	0.0177 (11)	0.0237 (11)	−0.0002 (9)	0.0001 (9)	−0.0073 (8)
C7	0.0207 (10)	0.0175 (10)	0.0190 (10)	0.0012 (8)	−0.0008 (8)	−0.0036 (8)
C8	0.0233 (10)	0.0202 (10)	0.0146 (9)	−0.0008 (8)	0.0001 (8)	−0.0074 (8)
C9	0.0272 (11)	0.0281 (11)	0.0104 (9)	−0.0022 (9)	−0.0006 (8)	−0.0006 (8)
C10	0.0259 (11)	0.0274 (11)	0.0114 (9)	−0.0025 (9)	0.0018 (8)	0.0014 (8)
C11	0.0235 (10)	0.0194 (10)	0.0155 (9)	−0.0012 (8)	−0.0005 (8)	0.0079 (8)
C12	0.0205 (10)	0.0175 (10)	0.0195 (10)	0.0008 (8)	0.0020 (8)	0.0034 (8)
C13	0.0320 (12)	0.0164 (10)	0.0272 (12)	−0.0003 (9)	−0.0001 (9)	0.0087 (8)
C14	0.0347 (13)	0.0111 (10)	0.0344 (13)	−0.0007 (9)	0.0005 (10)	0.0022 (9)
C15	0.0192 (10)	0.0146 (10)	0.0270 (11)	−0.0005 (8)	0.0018 (8)	−0.0043 (8)
C16	0.0137 (9)	0.0161 (9)	0.0192 (10)	−0.0008 (7)	−0.0002 (7)	0.0000 (8)
C17	0.0250 (11)	0.0232 (11)	0.0178 (10)	0.0007 (8)	0.0010 (8)	−0.0079 (8)
C18	0.0135 (9)	0.0124 (9)	0.0179 (10)	−0.0008 (7)	−0.0002 (7)	0.0002 (7)
C1S	0.0229 (10)	0.0114 (9)	0.0200 (10)	−0.0017 (7)	0.0006 (8)	−0.0005 (7)
C2S	0.0208 (11)	0.0254 (12)	0.0347 (13)	−0.0012 (8)	0.0004 (9)	0.0028 (9)
C3S	0.0537 (17)	0.0342 (14)	0.0161 (11)	0.0016 (11)	−0.0033 (11)	−0.0005 (9)

Geometric parameters (Å, º) top

Ni—N1	1.8503 (17)	C6—H6A	0.9500
Ni—N2	1.8502 (17)	C7—C8	1.430 (3)
Ni—O1	1.8609 (13)	C8—H8A	0.9500
Ni—O2	1.8594 (13)	C9—C10	1.499 (3)
O1—C1	1.313 (2)	C9—H9A	0.9900
O2—C18	1.311 (2)	C9—H9B	0.9900
O3—C2	1.372 (2)	C10—H10A	0.9900
O3—C3	1.427 (2)	C10—H10B	0.9900
O4—C16	1.370 (2)	C11—C12	1.429 (3)
O4—C17	1.428 (2)	C11—H11A	0.9500
O1S—C1S	1.228 (3)	C12—C18	1.413 (3)
N1—C8	1.290 (3)	C12—C13	1.416 (3)
N1—C9	1.479 (2)	C13—C14	1.363 (3)
N2—C11	1.293 (3)	C13—H13A	0.9500
N2—C10	1.482 (2)	C14—C15	1.407 (3)
N1S—C1S	1.341 (3)	C14—H14A	0.9500
N1S—C2S	1.451 (3)	C15—C16	1.378 (3)
N1S—C3S	1.451 (3)	C15—H15A	0.9500
C1—C7	1.414 (3)	C16—C18	1.433 (3)
C1—C2	1.433 (3)	C17—H17A	0.9800
C2—C4	1.379 (3)	C17—H17B	0.9800
C3—H3A	0.9800	C17—H17C	0.9800
C3—H3B	0.9800	C1S—H1SA	0.9500
C3—H3C	0.9800	C2S—H2SA	0.9800
C4—C5	1.406 (3)	C2S—H2SB	0.9800
C4—H4A	0.9500	C2S—H2SC	0.9800
C5—C6	1.366 (3)	C3S—H3SA	0.9800
C5—H5A	0.9500	C3S—H3SB	0.9800
C6—C7	1.413 (3)	C3S—H3SC	0.9800

N2—Ni—N1	85.71 (8)	C10—C9—H9B	110.1
N2—Ni—O2	94.66 (7)	H9A—C9—H9B	108.4
N1—Ni—O2	178.51 (7)	N2—C10—C9	107.53 (16)
N2—Ni—O1	179.01 (7)	N2—C10—H10A	110.2
N1—Ni—O1	94.51 (7)	C9—C10—H10A	110.2
O2—Ni—O1	85.14 (6)	N2—C10—H10B	110.2
C1—O1—Ni	126.96 (12)	C9—C10—H10B	110.2
C18—O2—Ni	127.00 (12)	H10A—C10—H10B	108.5
C2—O3—C3	116.94 (16)	N2—C11—C12	125.87 (19)
C16—O4—C17	117.06 (16)	N2—C11—H11A	117.1
C8—N1—C9	118.40 (17)	C12—C11—H11A	117.1
C8—N1—Ni	126.67 (15)	C18—C12—C13	120.97 (19)
C9—N1—Ni	114.85 (13)	C18—C12—C11	120.96 (19)
C11—N2—C10	118.33 (17)	C13—C12—C11	118.07 (19)
C11—N2—Ni	126.45 (14)	C14—C13—C12	120.9 (2)
C10—N2—Ni	115.16 (13)	C14—C13—H13A	119.6
C1S—N1S—C2S	120.44 (19)	C12—C13—H13A	119.6
C1S—N1S—C3S	121.1 (2)	C13—C14—C15	119.53 (19)
C2S—N1S—C3S	118.5 (2)	C13—C14—H14A	120.2
O1—C1—C7	124.57 (18)	C15—C14—H14A	120.2
O1—C1—C2	119.16 (17)	C16—C15—C14	120.6 (2)
C7—C1—C2	116.27 (18)	C16—C15—H15A	119.7
O3—C2—C4	123.86 (18)	C14—C15—H15A	119.7
O3—C2—C1	114.57 (17)	O4—C16—C15	124.02 (19)
C4—C2—C1	121.56 (18)	O4—C16—C18	114.50 (17)
O3—C3—H3A	109.5	C15—C16—C18	121.47 (19)
O3—C3—H3B	109.5	O4—C17—H17A	109.5
H3A—C3—H3B	109.5	O4—C17—H17B	109.5
O3—C3—H3C	109.5	H17A—C17—H17B	109.5
H3A—C3—H3C	109.5	O4—C17—H17C	109.5
H3B—C3—H3C	109.5	H17A—C17—H17C	109.5
C2—C4—C5	120.60 (19)	H17B—C17—H17C	109.5
C2—C4—H4A	119.7	O2—C18—C12	124.36 (18)
C5—C4—H4A	119.7	O2—C18—C16	119.15 (17)
C6—C5—C4	119.57 (19)	C12—C18—C16	116.49 (18)
C6—C5—H5A	120.2	O1S—C1S—N1S	125.1 (2)
C4—C5—H5A	120.2	O1S—C1S—H1SA	117.4
C5—C6—C7	120.8 (2)	N1S—C1S—H1SA	117.4
C5—C6—H6A	119.6	N1S—C2S—H2SA	109.5
C7—C6—H6A	119.6	N1S—C2S—H2SB	109.5
C6—C7—C1	121.21 (19)	H2SA—C2S—H2SB	109.5
C6—C7—C8	118.07 (19)	N1S—C2S—H2SC	109.5
C1—C7—C8	120.68 (19)	H2SA—C2S—H2SC	109.5
N1—C8—C7	125.91 (19)	H2SB—C2S—H2SC	109.5
N1—C8—H8A	117.0	N1S—C3S—H3SA	109.5
C7—C8—H8A	117.0	N1S—C3S—H3SB	109.5
N1—C9—C10	107.90 (16)	H3SA—C3S—H3SB	109.5
N1—C9—H9A	110.1	N1S—C3S—H3SC	109.5
C10—C9—H9A	110.1	H3SA—C3S—H3SC	109.5
N1—C9—H9B	110.1	H3SB—C3S—H3SC	109.5

N2—Ni—O1—C1	111 (4)	C2—C1—C7—C8	176.74 (18)
N1—Ni—O1—C1	8.14 (16)	C9—N1—C8—C7	−172.29 (19)
O2—Ni—O1—C1	−170.41 (16)	Ni—N1—C8—C7	4.3 (3)
N2—Ni—O2—C18	8.98 (16)	C6—C7—C8—N1	−179.6 (2)
N1—Ni—O2—C18	113 (3)	C1—C7—C8—N1	2.8 (3)
O1—Ni—O2—C18	−170.05 (16)	C8—N1—C9—C10	−156.46 (19)
N2—Ni—N1—C8	172.71 (18)	Ni—N1—C9—C10	26.6 (2)
O2—Ni—N1—C8	68 (3)	C11—N2—C10—C9	−157.70 (19)
O1—Ni—N1—C8	−8.25 (18)	Ni—N2—C10—C9	25.0 (2)
N2—Ni—N1—C9	−10.60 (14)	N1—C9—C10—N2	−31.2 (2)
O2—Ni—N1—C9	−115 (3)	C10—N2—C11—C12	−174.43 (19)
O1—Ni—N1—C9	168.43 (14)	Ni—N2—C11—C12	2.5 (3)
N1—Ni—N2—C11	174.22 (18)	N2—C11—C12—C18	3.5 (3)
O2—Ni—N2—C11	−7.22 (18)	N2—C11—C12—C13	−177.6 (2)
O1—Ni—N2—C11	71 (4)	C18—C12—C13—C14	−0.1 (3)
N1—Ni—N2—C10	−8.76 (14)	C11—C12—C13—C14	−179.0 (2)
O2—Ni—N2—C10	169.79 (14)	C12—C13—C14—C15	0.0 (3)
O1—Ni—N2—C10	−112 (4)	C13—C14—C15—C16	0.8 (3)
Ni—O1—C1—C7	−4.0 (3)	C17—O4—C16—C15	−3.2 (3)
Ni—O1—C1—C2	176.32 (13)	C17—O4—C16—C18	177.79 (16)
C3—O3—C2—C4	6.9 (3)	C14—C15—C16—O4	179.68 (19)
C3—O3—C2—C1	−173.86 (17)	C14—C15—C16—C18	−1.4 (3)
O1—C1—C2—O3	−0.4 (3)	Ni—O2—C18—C12	−6.0 (3)
C7—C1—C2—O3	179.85 (17)	Ni—O2—C18—C16	173.96 (13)
O1—C1—C2—C4	178.85 (18)	C13—C12—C18—O2	179.44 (19)
C7—C1—C2—C4	−0.9 (3)	C11—C12—C18—O2	−1.6 (3)
O3—C2—C4—C5	−179.16 (18)	C13—C12—C18—C16	−0.5 (3)
C1—C2—C4—C5	1.6 (3)	C11—C12—C18—C16	178.44 (18)
C2—C4—C5—C6	−0.7 (3)	O4—C16—C18—O2	0.3 (3)
C4—C5—C6—C7	−0.9 (3)	C15—C16—C18—O2	−178.73 (18)
C5—C6—C7—C1	1.6 (3)	O4—C16—C18—C12	−179.74 (17)
C5—C6—C7—C8	−175.9 (2)	C15—C16—C18—C12	1.2 (3)
O1—C1—C7—C6	179.6 (2)	C2S—N1S—C1S—O1S	179.27 (18)
C2—C1—C7—C6	−0.7 (3)	C3S—N1S—C1S—O1S	0.1 (3)
O1—C1—C7—C8	−3.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1S	0.95	2.62	3.310 (3)	130
C9—H9A···O2ⁱ	0.99	2.45	3.334 (3)	148
C10—H10A···O1ⁱⁱ	0.99	2.45	3.348 (3)	151

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₈H₁₈N₂O₄)]·C₃H₇NO
M_r	458.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	6.8601 (1), 15.3432 (3), 18.9065 (4)
β (°)	91.676 (2)
V (Å³)	1989.17 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.75
Crystal size (mm)	0.53 × 0.35 × 0.28

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.750, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7909, 3911, 3513
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.10
No. of reflections	3911
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.31

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni—N1	1.8503 (17)	Ni—O1	1.8609 (13)
Ni—N2	1.8502 (17)	Ni—O2	1.8594 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1S	0.95	2.62	3.310 (3)	130
C9—H9A···O2ⁱ	0.99	2.45	3.334 (3)	148
C10—H10A···O1ⁱⁱ	0.99	2.45	3.348 (3)	151

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

Acknowledgements

RJB wishes to acknowledge the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer. KA wishes to thank the National Science Foundation's AGEP Fellowship for support.

References

Abe, Y., Akao, H., Yoshida, Y., Takashima, H., Tanase, T., Mukai, H. & Ohta, K. (2006). Inorg. Chim. Acta, 359, 3147–3155. Web of Science CSD CrossRef CAS Google Scholar
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Assey, G., Gultneh, Y. & Butcher, R. J. (2010). Acta Cryst. E66, m654–m655. Web of Science CSD CrossRef IUCr Journals Google Scholar
Feng, X., Du, Z.-X., Ye, B.-X. & Cui, F.-N. (2007). Chin. J. Struct. Chem. 26, 1033–1038. CAS Google Scholar
Miyamura, K., Mihara, A., Fujii, T., Gohshi, Y. & Ishii, Y. (1995). J. Am. Chem. Soc. 117, 2377–2378. CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2009). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vasil'eva, S. V., Chepurnaya, I. A., Logvinov, S. A., Gaman'kov, P. V. & Timonov, A. M. (2003). Russ. J. Electrochem. 39, 310–313. CAS Google Scholar

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Volume 67| Part 3| March 2011| Page m328

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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′-[ethane-1,2-diylbis(nitrilo­methanylyl­­idene)]diphenolato}nickel(II) di­methyl­formamide monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}nickel(II) dimethylformamide monosolvate