[N,N'-Ethylenebis(salicylideneiminato)]nickel(II) dimethylformamide solvate

The title compound, [Ni(C₁₆H₁₄N₂O₂)]·C₃H₇NO, crystallizes with one Ni(salen) mol­ecule [salen is N,N'-ethyl­enebis­(salicyl­idene­iminate)] and one di­methyl­form­amide mol­ecule in the asymmetric unit. The molecular structure is similar to that of the solvent-free compound, known from the literature. In the crystal structure, the nearly planar mol­ecules are stacked to form polymeric chains in the crystallographic b direction. The crystal structure has pseudo-translational symmetry (superstructure).

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.027
• wR factor = 0.080
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          3
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         N3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000 and SORTAV (Blessing, 1997); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003).

[N,N'-Ethylenebis(salicylideneiminato)]nickel(II) dimethylformamide solvate

Crystal data

[Ni(C16H14N2O2)]·C3H7NO	F(000) = 832
Mr = 398.10	Dx = 1.476 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 57238 reflections
a = 13.3866 (2) Å	θ = 1.0–27.5°
b = 6.6690 (1) Å	µ = 1.11 mm^−1
c = 22.7332 (4) Å	T = 150 K
β = 118.0383 (7)°	Needle, red
V = 1791.31 (5) Å^3	0.58 × 0.08 × 0.06 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	4132 independent reflections
Radiation source: rotating anode	3209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −17→17
Tmin = 0.83, Tmax = 0.94	k = −8→8
36002 measured reflections	l = −29→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: difference Fourier map
wR(F^2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 0.3546P] where P = (Fo^2 + 2Fc^2)/3
4132 reflections	(Δ/σ)max = 0.002
249 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.530497 (15)	0.74371 (2)	0.522475 (9)	0.02046 (8)
O1	0.68607 (9)	0.76480 (14)	0.56822 (6)	0.0259 (2)
O2	0.54460 (9)	0.69921 (17)	0.60638 (5)	0.0269 (2)
N1	0.52056 (11)	0.77947 (17)	0.43927 (6)	0.0224 (3)
N2	0.37450 (11)	0.73126 (16)	0.47902 (7)	0.0218 (3)
C1	0.75651 (13)	0.7720 (2)	0.54287 (9)	0.0254 (3)
C2	0.72154 (14)	0.7834 (2)	0.47386 (9)	0.0261 (3)
C3	0.80395 (16)	0.7889 (2)	0.45134 (10)	0.0347 (4)
H3	0.7802	0.7968	0.4049	0.042*
C4	0.91710 (17)	0.7831 (3)	0.49536 (11)	0.0443 (5)
H4	0.9715	0.7864	0.4797	0.053*
C5	0.95167 (16)	0.7723 (3)	0.56366 (11)	0.0430 (5)
H5	1.0302	0.7680	0.5943	0.052*
C6	0.87408 (15)	0.7677 (2)	0.58747 (10)	0.0346 (4)
H6	0.8997	0.7617	0.6341	0.042*
C7	0.60420 (14)	0.7895 (2)	0.42575 (8)	0.0259 (3)
H7	0.5864 (14)	0.808 (3)	0.3821 (9)	0.028 (4)*
C8	0.46276 (13)	0.6869 (2)	0.62272 (8)	0.0257 (3)
C9	0.34640 (14)	0.7058 (2)	0.57627 (9)	0.0262 (3)
C10	0.26440 (15)	0.6927 (3)	0.59885 (9)	0.0348 (4)
H10	0.1867	0.7089	0.5678	0.042*
C11	0.29455 (17)	0.6574 (3)	0.66443 (10)	0.0419 (4)
H11	0.2386	0.6490	0.6788	0.050*
C12	0.40873 (17)	0.6339 (3)	0.70963 (9)	0.0426 (5)
H12	0.4301	0.6069	0.7550	0.051*
C13	0.49147 (16)	0.6489 (3)	0.69003 (9)	0.0367 (4)
H13	0.5687	0.6335	0.7221	0.044*
C14	0.30902 (14)	0.7234 (2)	0.50656 (9)	0.0263 (3)
H14	0.2267 (17)	0.719 (2)	0.4763 (10)	0.033 (5)*
C15	0.32218 (13)	0.7190 (2)	0.40559 (8)	0.0271 (3)
H15A	0.2504	0.7956	0.3851	0.033*
H15B	0.3053	0.5775	0.3910	0.033*
C16	0.40461 (13)	0.8057 (2)	0.38425 (8)	0.0264 (3)
H16A	0.3967	0.7360	0.3438	0.032*
H16B	0.3886	0.9500	0.3737	0.032*
O3	0.85282 (14)	1.0721 (2)	0.74247 (7)	0.0597 (4)
N3	0.87869 (12)	0.74635 (18)	0.77418 (7)	0.0309 (3)
C17	0.82376 (17)	0.8970 (3)	0.73340 (9)	0.0401 (4)
H17	0.7539 (16)	0.851 (3)	0.6945 (10)	0.047 (5)*
C18	0.8378 (2)	0.5422 (3)	0.75931 (12)	0.0622 (6)
H18A	0.8218	0.4922	0.7946	0.093*
H18B	0.8955	0.4575	0.7568	0.093*
H18C	0.7684	0.5385	0.7165	0.093*
C19	0.9836 (2)	0.7788 (3)	0.83410 (11)	0.0610 (7)
H19A	0.9749	0.7376	0.8728	0.092*
H19B	1.0034	0.9214	0.8380	0.092*
H19C	1.0437	0.6996	0.8323	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01799 (12)	0.02267 (12)	0.01915 (12)	−0.00080 (7)	0.00742 (8)	−0.00012 (7)
O1	0.0195 (5)	0.0326 (6)	0.0240 (6)	−0.0026 (4)	0.0089 (5)	−0.0012 (4)
O2	0.0236 (6)	0.0349 (6)	0.0216 (5)	−0.0010 (5)	0.0101 (5)	0.0006 (5)
N1	0.0228 (7)	0.0209 (6)	0.0212 (6)	0.0003 (5)	0.0086 (5)	0.0001 (5)
N2	0.0201 (6)	0.0210 (6)	0.0221 (6)	0.0007 (5)	0.0081 (5)	0.0008 (5)
C1	0.0229 (8)	0.0204 (7)	0.0335 (9)	−0.0025 (6)	0.0137 (7)	−0.0025 (6)
C2	0.0270 (8)	0.0205 (7)	0.0344 (9)	−0.0021 (6)	0.0174 (7)	−0.0019 (6)
C3	0.0356 (10)	0.0347 (9)	0.0422 (10)	−0.0044 (7)	0.0252 (8)	−0.0023 (7)
C4	0.0335 (10)	0.0535 (12)	0.0584 (13)	−0.0065 (8)	0.0321 (10)	−0.0088 (9)
C5	0.0225 (9)	0.0521 (12)	0.0523 (12)	−0.0048 (7)	0.0160 (8)	−0.0105 (9)
C6	0.0246 (8)	0.0389 (10)	0.0366 (10)	−0.0032 (7)	0.0112 (8)	−0.0059 (7)
C7	0.0326 (9)	0.0227 (8)	0.0245 (8)	−0.0015 (6)	0.0151 (7)	0.0003 (6)
C8	0.0323 (8)	0.0200 (7)	0.0275 (8)	−0.0019 (6)	0.0164 (7)	−0.0032 (6)
C9	0.0301 (8)	0.0206 (7)	0.0344 (9)	0.0013 (6)	0.0206 (7)	0.0003 (6)
C10	0.0360 (10)	0.0325 (8)	0.0456 (11)	0.0018 (7)	0.0273 (9)	0.0008 (8)
C11	0.0522 (12)	0.0390 (10)	0.0531 (12)	0.0031 (9)	0.0401 (10)	−0.0008 (9)
C12	0.0617 (13)	0.0440 (11)	0.0338 (10)	−0.0008 (9)	0.0321 (10)	−0.0041 (8)
C13	0.0417 (10)	0.0412 (10)	0.0291 (9)	−0.0010 (8)	0.0182 (8)	−0.0037 (7)
C14	0.0205 (8)	0.0233 (8)	0.0339 (9)	0.0012 (6)	0.0118 (7)	0.0023 (6)
C15	0.0210 (8)	0.0314 (8)	0.0222 (8)	−0.0010 (6)	0.0047 (6)	0.0017 (6)
C16	0.0261 (8)	0.0283 (8)	0.0212 (8)	0.0007 (6)	0.0081 (6)	0.0032 (6)
O3	0.0895 (12)	0.0333 (7)	0.0569 (9)	0.0094 (7)	0.0350 (9)	0.0086 (7)
N3	0.0297 (8)	0.0296 (7)	0.0257 (7)	0.0003 (5)	0.0066 (6)	−0.0007 (5)
C17	0.0462 (11)	0.0406 (10)	0.0295 (9)	0.0105 (9)	0.0143 (9)	0.0026 (8)
C18	0.0729 (15)	0.0347 (10)	0.0594 (14)	−0.0095 (10)	0.0149 (12)	−0.0048 (10)
C19	0.0445 (13)	0.0583 (14)	0.0458 (13)	−0.0053 (10)	−0.0073 (10)	0.0029 (10)

Geometric parameters (Å, º)

Ni1—O1	1.8445 (11)	C9—C10	1.416 (2)
Ni1—N2	1.8451 (13)	C9—C14	1.425 (2)
Ni1—N1	1.8483 (13)	C10—C11	1.369 (3)
Ni1—O2	1.8503 (11)	C10—H10	0.9500
Ni1—Ni1^i	3.3901 (3)	C11—C12	1.393 (3)
Ni1—Ni1^ii	3.5513 (3)	C11—H11	0.9500
O1—C1	1.317 (2)	C12—C13	1.378 (2)
O2—C8	1.3143 (18)	C12—H12	0.9500
N1—C7	1.295 (2)	C13—H13	0.9500
N1—C16	1.4762 (19)	C14—H14	0.99 (2)
N2—C14	1.296 (2)	C15—C16	1.514 (2)
N2—C15	1.478 (2)	C15—H15A	0.9900
C1—C2	1.413 (2)	C15—H15B	0.9900
C1—C6	1.416 (2)	C16—H16A	0.9900
C2—C3	1.418 (2)	C16—H16B	0.9900
C2—C7	1.432 (2)	O3—C17	1.218 (2)
C3—C4	1.368 (3)	N3—C17	1.330 (2)
C3—H3	0.9500	N3—C19	1.441 (2)
C4—C5	1.398 (3)	N3—C18	1.447 (2)
C4—H4	0.9500	C17—H17	0.99 (2)
C5—C6	1.379 (3)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—H6	0.9500	C18—H18C	0.9800
C7—H7	0.914 (18)	C19—H19A	0.9800
C8—C13	1.414 (2)	C19—H19B	0.9800
C8—C9	1.418 (2)	C19—H19C	0.9800
O1—Ni1—N2	177.53 (5)	C10—C9—C14	118.78 (16)
O1—Ni1—N1	94.94 (5)	C8—C9—C14	121.61 (14)
N2—Ni1—N1	86.50 (6)	C11—C10—C9	121.55 (17)
O1—Ni1—O2	83.69 (5)	C11—C10—H10	119.2
N2—Ni1—O2	94.94 (5)	C9—C10—H10	119.2
N1—Ni1—O2	177.62 (5)	C10—C11—C12	118.82 (16)
O1—Ni1—Ni1^i	106.93 (3)	C10—C11—H11	120.6
N2—Ni1—Ni1^i	75.16 (3)	C12—C11—H11	120.6
N1—Ni1—Ni1^i	85.64 (4)	C13—C12—C11	121.55 (17)
O2—Ni1—Ni1^i	92.89 (4)	C13—C12—H12	119.2
O1—Ni1—Ni1^ii	97.74 (3)	C11—C12—H12	119.2
N2—Ni1—Ni1^ii	80.79 (3)	C12—C13—C8	120.78 (17)
N1—Ni1—Ni1^ii	71.65 (4)	C12—C13—H13	119.6
O2—Ni1—Ni1^ii	110.44 (4)	C8—C13—H13	119.6
Ni1^i—Ni1—Ni1^ii	147.779 (11)	N2—C14—C9	125.24 (15)
C1—O1—Ni1	127.37 (11)	N2—C14—H14	116.8 (12)
C8—O2—Ni1	127.35 (10)	C9—C14—H14	117.8 (12)
C7—N1—C16	118.36 (14)	N2—C15—C16	108.12 (12)
C7—N1—Ni1	126.54 (12)	N2—C15—H15A	110.1
C16—N1—Ni1	115.07 (10)	C16—C15—H15A	110.1
C14—N2—C15	118.32 (14)	N2—C15—H15B	110.1
C14—N2—Ni1	126.56 (12)	C16—C15—H15B	110.1
C15—N2—Ni1	115.04 (10)	H15A—C15—H15B	108.4
O1—C1—C2	123.80 (14)	N1—C16—C15	108.52 (12)
O1—C1—C6	117.99 (15)	N1—C16—H16A	110.0
C2—C1—C6	118.22 (15)	C15—C16—H16A	110.0
C1—C2—C3	119.63 (16)	N1—C16—H16B	110.0
C1—C2—C7	121.45 (15)	C15—C16—H16B	110.0
C3—C2—C7	118.92 (16)	H16A—C16—H16B	108.4
C4—C3—C2	121.12 (18)	C17—N3—C19	121.29 (16)
C4—C3—H3	119.4	C17—N3—C18	121.56 (17)
C2—C3—H3	119.4	C19—N3—C18	117.12 (15)
C3—C4—C5	119.23 (17)	O3—C17—N3	125.35 (19)
C3—C4—H4	120.4	O3—C17—H17	123.0 (12)
C5—C4—H4	120.4	N3—C17—H17	111.7 (12)
C6—C5—C4	121.33 (18)	N3—C18—H18A	109.5
C6—C5—H5	119.3	N3—C18—H18B	109.5
C4—C5—H5	119.3	H18A—C18—H18B	109.5
C5—C6—C1	120.47 (18)	N3—C18—H18C	109.5
C5—C6—H6	119.8	H18A—C18—H18C	109.5
C1—C6—H6	119.8	H18B—C18—H18C	109.5
N1—C7—C2	125.30 (15)	N3—C19—H19A	109.5
N1—C7—H7	116.9 (11)	N3—C19—H19B	109.5
C2—C7—H7	117.8 (11)	H19A—C19—H19B	109.5
O2—C8—C13	118.57 (15)	N3—C19—H19C	109.5
O2—C8—C9	123.62 (14)	H19A—C19—H19C	109.5
C13—C8—C9	117.80 (15)	H19B—C19—H19C	109.5
C10—C9—C8	119.46 (16)
N1—Ni1—O1—C1	−8.57 (11)	C3—C4—C5—C6	−0.1 (3)
O2—Ni1—O1—C1	169.47 (11)	C4—C5—C6—C1	0.6 (3)
Ni1^i—Ni1—O1—C1	78.36 (11)	O1—C1—C6—C5	179.18 (14)
Ni1^ii—Ni1—O1—C1	−80.68 (11)	C2—C1—C6—C5	−0.8 (2)
O1—Ni1—O2—C8	171.96 (13)	C16—N1—C7—C2	174.74 (14)
N2—Ni1—O2—C8	−5.97 (13)	Ni1—N1—C7—C2	−2.9 (2)
Ni1^i—Ni1—O2—C8	−81.31 (12)	C1—C2—C7—N1	−2.2 (2)
Ni1^ii—Ni1—O2—C8	76.03 (13)	C3—C2—C7—N1	177.83 (14)
O1—Ni1—N1—C7	6.89 (13)	Ni1—O2—C8—C13	179.06 (11)
N2—Ni1—N1—C7	−175.13 (13)	Ni1—O2—C8—C9	0.3 (2)
Ni1^i—Ni1—N1—C7	−99.76 (12)	O2—C8—C9—C10	−179.23 (15)
Ni1^ii—Ni1—N1—C7	103.42 (13)	C13—C8—C9—C10	2.0 (2)
O1—Ni1—N1—C16	−170.84 (10)	O2—C8—C9—C14	5.3 (2)
N2—Ni1—N1—C16	7.15 (10)	C13—C8—C9—C14	−173.41 (15)
Ni1^i—Ni1—N1—C16	82.51 (10)	C8—C9—C10—C11	−1.6 (3)
Ni1^ii—Ni1—N1—C16	−74.31 (9)	C14—C9—C10—C11	173.98 (16)
N1—Ni1—N2—C14	−173.38 (12)	C9—C10—C11—C12	0.0 (3)
O2—Ni1—N2—C14	8.52 (12)	C10—C11—C12—C13	1.1 (3)
Ni1^i—Ni1—N2—C14	100.21 (12)	C11—C12—C13—C8	−0.6 (3)
Ni1^ii—Ni1—N2—C14	−101.42 (12)	O2—C8—C13—C12	−179.77 (15)
N1—Ni1—N2—C15	9.90 (10)	C9—C8—C13—C12	−1.0 (2)
O2—Ni1—N2—C15	−168.19 (9)	C15—N2—C14—C9	170.98 (14)
Ni1^i—Ni1—N2—C15	−76.51 (9)	Ni1—N2—C14—C9	−5.6 (2)
Ni1^ii—Ni1—N2—C15	81.86 (9)	C10—C9—C14—N2	−178.07 (15)
Ni1—O1—C1—C2	6.24 (19)	C8—C9—C14—N2	−2.6 (2)
Ni1—O1—C1—C6	−173.69 (10)	C14—N2—C15—C16	159.46 (13)
O1—C1—C2—C3	−179.54 (13)	Ni1—N2—C15—C16	−23.54 (14)
C6—C1—C2—C3	0.4 (2)	C7—N1—C16—C15	160.61 (13)
O1—C1—C2—C7	0.5 (2)	Ni1—N1—C16—C15	−21.47 (15)
C6—C1—C2—C7	−179.60 (13)	N2—C15—C16—N1	27.36 (16)
C1—C2—C3—C4	0.1 (2)	C19—N3—C17—O3	−2.0 (3)
C7—C2—C3—C4	−179.90 (16)	C18—N3—C17—O3	−180.0 (2)
C2—C3—C4—C5	−0.3 (3)

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