{6,6'-Dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methanylyl-idene)]diphenolato}nickel(II) dimethyl-formamide monosolvate.

In the title compound, [Ni(C(18)H(18)N(2)O(4))]·C(3)H(7)NO, the central Ni(II) atom is in a square-planar O(2)N(2) 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 inter-molecular C-H⋯O inter-actions involving the dimethyl-formamide 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 = 458.15

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.10

3911 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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.

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

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

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

[Ni(C18H18N2O4)]·C3H7NO	F(000) = 960
Mr = 458.15	Dx = 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

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	Rint = 0.020
Detector resolution: 10.5081 pixels mm-1	θmax = 74.1°, θmin = 5.5°
ω scans	h = −8→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −18→18
Tmin = 0.750, Tmax = 1.000	l = −22→23
7909 measured reflections

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(Fo2) + (0.0443P)2 + 2.5615P] where P = (Fo2 + 2Fc2)/3
3911 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .