[N,N'-Bis­(salicyl­idene)-1,2-di­phenyl-(RS,SR)-1,2-ethane­di­amin­ato]­nickel(II)

In crystals of the title compound, [Ni(C₂₈H₂₂N₂O₂)], the coordination geometry around the Ni atom is square planar with a slight tetrahedral distortion. The five-membered N,N'-chelate ring adopts a distorted gauche conformation with the two phenyl groups in axial and equatorial orientations.

S1. Comment

The thermal dehydrogenation reaction of [Ni(3-EtOsal-meso-stien)] with [VO(salen)]NO₃ in the solid state has been investigated by Hoshina et al. (2000), where H₂(3-EtOsal-meso-stien) is N,N'-bis(3-ethoxysalicylidene)-1,2-diphenyl-1,2-ethanediamine. The crystal structure of [Ni(sal-meso-stien)], (I), is presented here, where sal-meso-stien is N,N'-bis(salicylidene)-1,2-diphenyl-1,2-ethanediamine.

S2. Experimental

The title complex, [Ni(sal-meso-stien)], was prepared by the reaction of a hot methanol solution (30 ml) of nickel(II) acetate tetrahydrate (0.249 g, 1 mmol) with the Schiff base ligand H₂(sal-meso-stien) (0.421 g, 1 mmol). The resulting red–brown precipitate was collected by filtration and washed with ether (yield 90%). The red crystals of [Ni(sal-meso-stien)] were grown by slow evaporation of an acetonitrile solution.

S3. Refinement

All H-atom positions were calculated geometrically and fixed with U_iso(H) = 1.2U_eq(parent atom).

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

[Ni(C28H22N2O2)]	Dx = 1.402 Mg m^−3
Mr = 477.19	Mo Kα radiation, λ = 0.7107 Å
Monoclinic, P21/n	Cell parameters from 25 reflections
a = 12.517 (2) Å	θ = 14.2–14.9°
b = 11.500 (3) Å	µ = 0.89 mm^−1
c = 16.413 (2) Å	T = 297 K
β = 106.893 (9)°	Prismatic, red
V = 2260.7 (6) Å^3	0.5 × 0.4 × 0.3 mm
Z = 4

Data collection

Rigaku AFC5 diffractometer	Rint = 0.026
θ–2θ scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→16
Tmin = 0.658, Tmax = 0.766	k = 0→14
5415 measured reflections	l = −21→21
5182 independent reflections	3 standard reflections every 100 reflections
3469 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.2639P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.109	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.47 e Å^−3
3469 reflections	Δρmin = −0.28 e Å^−3
298 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.96970 (3)	0.05304 (3)	0.38683 (2)	0.0343 (1)
O2	0.8198 (2)	0.0904 (2)	0.3531 (1)	0.0419 (5)
O3	0.9876 (2)	0.1981 (2)	0.4362 (1)	0.0403 (4)
N4	0.9512 (2)	−0.0857 (2)	0.3275 (1)	0.0366 (5)
N5	1.1168 (2)	0.0081 (2)	0.4355 (1)	0.0357 (5)
C6	0.7365 (2)	0.0250 (2)	0.3103 (2)	0.0373 (6)
C7	0.6262 (2)	0.0610 (3)	0.3039 (2)	0.0448 (7)
C8	0.5364 (3)	−0.0037 (3)	0.2591 (2)	0.0502 (7)
C9	0.5501 (3)	−0.1061 (3)	0.2183 (2)	0.0535 (8)
C10	0.6557 (3)	−0.1444 (3)	0.2248 (2)	0.0475 (7)
C11	0.7503 (2)	−0.0813 (2)	0.2712 (2)	0.0381 (6)
C12	0.8583 (3)	−0.1302 (2)	0.2819 (2)	0.0402 (6)
C13	1.0567 (2)	−0.1489 (2)	0.3339 (2)	0.0414 (7)
C14	1.1064 (2)	−0.1177 (3)	0.2629 (2)	0.0460 (7)
C15	1.1017 (3)	−0.0075 (4)	0.2302 (2)	0.0608 (9)
C16	1.1554 (4)	0.0173 (4)	0.1681 (3)	0.084 (1)
C17	1.2135 (4)	−0.0694 (6)	0.1406 (3)	0.094 (2)
C18	1.2174 (4)	−0.1767 (5)	0.1723 (3)	0.087 (1)
C19	1.1638 (3)	−0.2041 (4)	0.2329 (2)	0.065 (1)
C20	1.1320 (2)	−0.1190 (3)	0.4247 (2)	0.0392 (6)
C21	1.2507 (3)	−0.1625 (3)	0.4468 (2)	0.0450 (7)
C22	1.3320 (3)	−0.1122 (3)	0.4152 (2)	0.0599 (9)
C23	1.4397 (3)	−0.1534 (4)	0.4394 (3)	0.078 (1)
C24	1.4681 (3)	−0.2463 (4)	0.4939 (3)	0.084 (1)
C25	1.3896 (4)	−0.2980 (4)	0.5261 (2)	0.073 (1)
C26	1.2804 (3)	−0.2555 (3)	0.5021 (2)	0.0560 (9)
C27	1.1940 (2)	0.0677 (3)	0.4879 (2)	0.0393 (6)
C28	1.1825 (2)	0.1855 (2)	0.5125 (2)	0.0373 (6)
C29	1.2747 (2)	0.2416 (3)	0.5694 (2)	0.0483 (7)
C30	1.2674 (3)	0.3516 (3)	0.5979 (2)	0.0570 (9)
C31	1.1660 (3)	0.4094 (3)	0.5722 (2)	0.0576 (9)
C32	1.0740 (3)	0.3575 (3)	0.5177 (2)	0.0508 (8)
C33	1.0791 (2)	0.2442 (2)	0.4863 (2)	0.0366 (6)
H7	0.6145	0.1316	0.3302	0.0535*
H8	0.4635	0.0225	0.2555	0.0618*
H9	0.4876	−0.1480	0.1846	0.0642*
H10	0.6661	−0.2165	0.1988	0.0559*
H12	0.8624	−0.2023	0.2542	0.0490*
H13	1.0410	−0.2303	0.3313	0.0496*
H15	1.0586	0.0544	0.2493	0.0762*
H16	1.1530	0.0956	0.1432	0.0995*
H17	1.2528	−0.0523	0.0982	0.1118*
H18	1.2576	−0.2399	0.1514	0.1064*
H19	1.1674	−0.2847	0.2571	0.0779*
H20	1.0992	−0.1574	0.4633	0.0467*
H22	1.3117	−0.0464	0.3750	0.0719*
H23	1.4966	−0.1162	0.4175	0.0936*
H24	1.5443	−0.2734	0.5116	0.0978*
H25	1.4097	−0.3659	0.5646	0.0869*
H26	1.2249	−0.2908	0.5247	0.0661*
H27	1.2639	0.0302	0.5129	0.0483*
H29	1.3439	0.2016	0.5878	0.0577*
H30	1.3307	0.3887	0.6350	0.0703*
H31	1.1596	0.4855	0.5926	0.0706*
H32	1.0052	0.3998	0.5001	0.0618*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0358 (2)	0.0332 (2)	0.0339 (2)	0.0035 (2)	0.0100 (1)	0.0002 (2)
O2	0.036 (1)	0.039 (1)	0.048 (1)	0.0033 (8)	0.0078 (9)	−0.0050 (9)
O3	0.038 (1)	0.036 (1)	0.042 (1)	0.0041 (8)	0.0048 (8)	−0.0037 (9)
N4	0.039 (1)	0.035 (1)	0.037 (1)	0.0025 (10)	0.014 (1)	−0.0002 (9)
N5	0.040 (1)	0.037 (1)	0.032 (1)	0.006 (1)	0.014 (1)	0.0025 (10)
C6	0.039 (2)	0.037 (2)	0.034 (1)	0.000 (1)	0.007 (1)	0.003 (1)
C7	0.043 (2)	0.045 (2)	0.045 (2)	0.002 (1)	0.011 (1)	−0.003 (1)
C8	0.038 (2)	0.057 (2)	0.055 (2)	0.003 (1)	0.012 (1)	−0.001 (2)
C9	0.043 (2)	0.062 (2)	0.050 (2)	−0.006 (2)	0.005 (1)	−0.007 (2)
C10	0.052 (2)	0.045 (2)	0.043 (2)	−0.005 (1)	0.009 (1)	−0.004 (1)
C11	0.041 (1)	0.038 (2)	0.035 (1)	−0.001 (1)	0.012 (1)	0.001 (1)
C12	0.050 (2)	0.036 (1)	0.037 (1)	−0.002 (1)	0.016 (1)	−0.003 (1)
C13	0.045 (2)	0.036 (2)	0.048 (2)	0.005 (1)	0.021 (1)	−0.001 (1)
C14	0.041 (2)	0.060 (2)	0.038 (2)	0.001 (1)	0.013 (1)	−0.006 (1)
C15	0.063 (2)	0.076 (2)	0.046 (2)	−0.002 (2)	0.020 (2)	0.006 (2)
C16	0.084 (3)	0.116 (4)	0.051 (2)	−0.023 (3)	0.019 (2)	0.017 (2)
C17	0.067 (3)	0.177 (6)	0.048 (2)	−0.024 (3)	0.031 (2)	−0.014 (3)
C18	0.067 (3)	0.142 (5)	0.062 (3)	−0.004 (3)	0.034 (2)	−0.034 (3)
C19	0.058 (2)	0.086 (3)	0.057 (2)	0.003 (2)	0.024 (2)	−0.024 (2)
C20	0.044 (2)	0.039 (2)	0.037 (1)	0.010 (1)	0.016 (1)	0.007 (1)
C21	0.048 (2)	0.049 (2)	0.038 (2)	0.015 (1)	0.012 (1)	−0.001 (1)
C22	0.050 (2)	0.068 (2)	0.063 (2)	0.018 (2)	0.019 (2)	0.011 (2)
C23	0.051 (2)	0.103 (3)	0.080 (3)	0.021 (2)	0.023 (2)	0.010 (3)
C24	0.062 (3)	0.115 (4)	0.069 (3)	0.039 (3)	0.010 (2)	0.003 (3)
C25	0.089 (3)	0.072 (3)	0.050 (2)	0.043 (2)	0.007 (2)	0.007 (2)
C26	0.071 (2)	0.055 (2)	0.041 (2)	0.019 (2)	0.015 (2)	0.001 (1)
C27	0.036 (1)	0.050 (2)	0.032 (1)	0.009 (1)	0.010 (1)	0.007 (1)
C28	0.038 (1)	0.044 (2)	0.030 (1)	0.001 (1)	0.010 (1)	0.001 (1)
C29	0.037 (2)	0.063 (2)	0.043 (2)	0.004 (1)	0.009 (1)	0.000 (1)
C30	0.052 (2)	0.058 (2)	0.053 (2)	−0.011 (2)	0.001 (2)	−0.010 (2)
C31	0.062 (2)	0.046 (2)	0.056 (2)	−0.002 (2)	0.002 (2)	−0.010 (2)
C32	0.051 (2)	0.041 (2)	0.052 (2)	0.004 (1)	0.003 (1)	−0.005 (1)
C33	0.039 (1)	0.039 (1)	0.030 (1)	0.000 (1)	0.006 (1)	0.003 (1)

Geometric parameters (Å, º)

Ni—O2	1.846 (2)	C17—C18	1.335 (9)
Ni—O3	1.840 (2)	C17—H17	0.982
Ni—N4	1.848 (2)	C18—C19	1.388 (7)
Ni—N5	1.855 (2)	C18—H18	1.000
O2—C6	1.312 (3)	C19—H19	1.004
O3—C33	1.312 (3)	C20—C21	1.508 (4)
N4—C12	1.291 (3)	C20—H20	0.959
N4—C13	1.484 (4)	C21—C22	1.395 (5)
N5—C20	1.491 (4)	C21—C26	1.383 (4)
N5—C27	1.289 (3)	C22—C23	1.374 (5)
C6—C7	1.415 (4)	C22—H22	0.988
C6—C11	1.414 (4)	C23—C24	1.372 (7)
C7—C8	1.370 (4)	C23—H23	0.985
C7—H7	0.951	C24—C25	1.378 (7)
C8—C9	1.390 (5)	C24—H24	0.965
C8—H8	0.946	C25—C26	1.397 (6)
C9—C10	1.368 (5)	C25—H25	0.990
C9—H9	0.948	C26—H26	0.966
C10—C11	1.410 (4)	C27—C28	1.433 (4)
C10—H10	0.959	C27—H27	0.954
C11—C12	1.427 (4)	C28—C29	1.412 (4)
C12—H12	0.954	C28—C33	1.412 (4)
C13—C14	1.515 (5)	C29—C30	1.361 (5)
C13—C20	1.552 (4)	C29—H29	0.949
C13—H13	0.955	C30—C31	1.385 (5)
C14—C15	1.371 (5)	C30—H30	0.948
C14—C19	1.398 (5)	C31—C32	1.373 (4)
C15—C16	1.403 (6)	C31—H31	0.949
C15—H15	0.997	C32—C33	1.409 (4)
C16—C17	1.384 (8)	C32—H32	0.957
C16—H16	0.986
O2—Ni—O3	84.49 (8)	C18—C17—H17	119.5
O2—Ni—N4	94.70 (9)	C17—C18—C19	121.3 (5)
O2—Ni—N5	171.6 (1)	C17—C18—H18	120.2
O3—Ni—N4	174.53 (10)	C19—C18—H18	118.5
O3—Ni—N5	94.85 (9)	C14—C19—C18	119.7 (4)
N4—Ni—N5	86.74 (10)	C14—C19—H19	119.0
Ni—O2—C6	127.4 (2)	C18—C19—H19	121.3
Ni—O3—C33	127.9 (2)	N5—C20—C13	105.6 (2)
Ni—N4—C12	127.0 (2)	N5—C20—C21	116.6 (2)
Ni—N4—C13	114.4 (2)	N5—C20—H20	106.1
C12—N4—C13	118.7 (2)	C13—C20—C21	116.0 (3)
Ni—N5—C20	111.5 (2)	C13—C20—H20	106.0
Ni—N5—C27	126.6 (2)	C21—C20—H20	105.6
C20—N5—C27	120.3 (2)	C20—C21—C22	123.2 (3)
O2—C6—C7	118.6 (3)	C20—C21—C26	118.2 (3)
O2—C6—C11	123.7 (3)	C22—C21—C26	118.6 (3)
C7—C6—C11	117.7 (2)	C21—C22—C23	120.7 (3)
C6—C7—C8	120.8 (3)	C21—C22—H22	119.5
C6—C7—H7	119.4	C23—C22—H22	119.8
C8—C7—H7	119.8	C22—C23—C24	120.2 (4)
C7—C8—C9	121.4 (3)	C22—C23—H23	119.9
C7—C8—H8	119.1	C24—C23—H23	119.9
C9—C8—H8	119.4	C23—C24—C25	120.5 (4)
C8—C9—C10	119.2 (3)	C23—C24—H24	119.6
C8—C9—H9	121.0	C25—C24—H24	119.8
C10—C9—H9	119.8	C24—C25—C26	119.3 (4)
C9—C10—C11	121.2 (3)	C24—C25—H25	120.5
C9—C10—H10	119.9	C26—C25—H25	120.2
C11—C10—H10	119.0	C21—C26—C25	120.7 (4)
C6—C11—C10	119.7 (3)	C21—C26—H26	119.4
C6—C11—C12	121.4 (2)	C25—C26—H26	120.0
C10—C11—C12	118.7 (3)	N5—C27—C28	125.0 (2)
N4—C12—C11	125.1 (3)	N5—C27—H27	117.5
N4—C12—H12	117.2	C28—C27—H27	117.5
C11—C12—H12	117.7	C27—C28—C29	119.2 (2)
N4—C13—C14	112.7 (2)	C27—C28—C33	121.6 (2)
N4—C13—C20	103.9 (2)	C29—C28—C33	119.0 (3)
N4—C13—H13	108.0	C28—C29—C30	121.9 (3)
C14—C13—C20	114.5 (2)	C28—C29—H29	118.9
C14—C13—H13	108.8	C30—C29—H29	119.2
C20—C13—H13	108.7	C29—C30—C31	119.2 (3)
C13—C14—C15	122.7 (3)	C29—C30—H30	120.8
C13—C14—C19	118.1 (3)	C31—C30—H30	120.1
C15—C14—C19	119.2 (3)	C30—C31—C32	120.8 (3)
C14—C15—C16	119.8 (4)	C30—C31—H31	119.9
C14—C15—H15	120.1	C32—C31—H31	119.4
C16—C15—H15	120.0	C31—C32—C33	121.4 (3)
C15—C16—C17	119.9 (5)	C31—C32—H32	119.1
C15—C16—H16	121.5	C33—C32—H32	119.5
C17—C16—H16	118.6	O3—C33—C28	123.6 (2)
C16—C17—C18	120.1 (5)	O3—C33—C32	118.6 (2)
C16—C17—H17	120.4	C28—C33—C32	117.7 (2)