The exo and endo isomers of [N,N′-bis­(salicyl­idene)-1,2-di­phenyl-(RS,SR)-1,2-ethane­diyl­diamin­ato]­oxo­vanadium(IV)

Hoshina, G.; Tsuchimoto, M.; Ohba, S.

doi:10.1107/S0108270100004509

The exo and endo isomers of [N,N'-bis(salicylidene)-1,2-diphenyl-(RS,SR)-1,2-ethanediyldiaminato]oxovanadium(IV)

The title complexes, exo- and endo-[VO(C₂₈H₂₂N₂O₂)], show monomeric structures with a distorted square-pyramidal coordination. The two phenyl groups on the five-membered N,N'-chelate ring are both on the same side as the oxo ligand for the exo isomer and on opposite sides for the endo isomer.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004509/qa0255sup1.cif Contains datablocks vostien, exo, endo
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004509/qa0255exosup2.hkl Contains datablock exo
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004509/qa0255endosup3.hkl Contains datablock endo

CCDC references: 145633; 145634

Comment top

The crystal structures of the monomeric and polymeric forms of [VO{sal-(RR)-stien}] were reported by Nakajima et al. (1996). The crystal structures and the thermal isomerization of [VO(3-EtOsal-meso-stien)] have been investigated by the authors (Hoshina et al., 1999), together with the thermal dehydrogenation in the solid state (Hoshina et al., 1998, 2000).

The title complex, [VO(sal-meso-stien)], (I), did not show thermal isomerization in the solid state below 463 K. The endo isomer was more reactive in dehydrogenation upon heating in air than the exo isomer.

Experimental top

The exo-[VO(sal-meso-stien)] isomer was prepared selectively by the reaction of vanadium(IV) oxide sulfate (0.25 g, 1 mmol) with the Schiff base ligand H₂sal-meso-stien (0.42 g, 1 mmol) in methanol containing pyridine (yield 74%). The endo isomer was prepared separately by the reaction of vanadium(IV) oxide sulfate (0.25 g, 1 mmol) and H₂sal-meso-stien (0.42 g, 1 mmol) in methanol without pyridine (yield 86%). The endo-[VO(sal-meso-stien)] isomer was eluted more slowly than the exo isomer by high-performance liquid reversed-phase chromatography using CH₃CN/H₂O (1:1 v/v) as eluent.

Computing details top

For both compounds, 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.

(exo) top

Crystal data top

[VO(C₂₈H₂₂N₂O₂)]	D_x = 1.369 Mg m⁻³
M_r = 485.43	Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P2₁/n	Cell parameters from 25 reflections
a = 13.278 (2) Å	θ = 14.9–15.0°
b = 11.340 (3) Å	µ = 0.45 mm⁻¹
c = 15.940 (2) Å	T = 297 K
β = 101.12 (1)°	Prismatic, green
V = 2355.1 (7) Å³	0.7 × 0.2 × 0.2 mm
Z = 4

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.016
θ–2θ scans	θ_max = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −17→0
T_min = 0.881, T_max = 0.915	k = 0→14
5646 measured reflections	l = −20→20
5417 independent reflections	3 standard reflections every 150 reflections
3380 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0505P)² + 1.8247P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.133	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.81 e Å⁻³
5417 reflections	Δρ_min = −0.33 e Å⁻³
307 parameters

Crystal data top

[VO(C₂₈H₂₂N₂O₂)]	V = 2355.1 (7) Å³
M_r = 485.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.278 (2) Å	µ = 0.45 mm⁻¹
b = 11.340 (3) Å	T = 297 K
c = 15.940 (2) Å	0.7 × 0.2 × 0.2 mm
β = 101.12 (1)°

Data collection top

Rigaku AFC-7R diffractometer	3380 reflections with I > 2σ(I)
Absorption correction: integration (Coppens et al., 1965)	R_int = 0.016
T_min = 0.881, T_max = 0.915	3 standard reflections every 150 reflections
5646 measured reflections	intensity decay: none
5417 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	307 parameters
wR(F²) = 0.133	H-atom parameters not refined
S = 1.03	Δρ_max = 0.81 e Å⁻³
5417 reflections	Δρ_min = −0.33 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
V1	0.33135 (4)	0.06424 (4)	0.96503 (3)	0.0321 (1)
O2	0.2178 (2)	0.1141 (2)	0.9610 (1)	0.0484 (5)
O3	0.4234 (2)	0.1951 (2)	0.9942 (1)	0.0417 (5)
O4	0.3685 (1)	0.0718 (2)	0.8542 (1)	0.0357 (4)
N5	0.3829 (2)	−0.0008 (2)	1.0859 (1)	0.0334 (5)
N6	0.3111 (2)	−0.1141 (2)	0.9450 (1)	0.0334 (5)
C7	0.4524 (2)	0.2456 (3)	1.0698 (2)	0.0392 (7)
C8	0.4900 (3)	0.3619 (3)	1.0731 (2)	0.0550 (9)
C9	0.5258 (3)	0.4159 (3)	1.1509 (3)	0.066 (1)
C10	0.5267 (3)	0.3570 (4)	1.2270 (3)	0.067 (1)
C11	0.4907 (3)	0.2443 (3)	1.2246 (2)	0.0529 (8)
C12	0.4523 (2)	0.1858 (3)	1.1470 (2)	0.0385 (6)
C13	0.4259 (2)	0.0632 (3)	1.1502 (2)	0.0390 (6)
C14	0.3840 (2)	−0.1316 (3)	1.0981 (2)	0.0351 (6)
C15	0.3650 (2)	−0.1736 (3)	1.1838 (2)	0.0433 (7)
C16	0.2891 (3)	−0.1261 (4)	1.2221 (2)	0.0563 (9)
C17	0.2729 (3)	−0.1714 (5)	1.2994 (3)	0.080 (1)
C18	0.3302 (5)	−0.2634 (6)	1.3376 (3)	0.098 (2)
C19	0.4043 (5)	−0.3105 (5)	1.3004 (3)	0.100 (2)
C20	0.4237 (3)	−0.2653 (4)	1.2233 (3)	0.066 (1)
C21	0.3126 (2)	−0.1906 (2)	1.0213 (2)	0.0346 (6)
C22	0.2044 (2)	−0.2206 (3)	1.0331 (2)	0.0401 (7)
C23	0.1251 (3)	−0.1409 (4)	1.0192 (3)	0.062 (1)
C24	0.0277 (3)	−0.1733 (5)	1.0304 (3)	0.075 (1)
C25	0.0086 (3)	−0.2838 (5)	1.0539 (3)	0.076 (1)
C26	0.0858 (4)	−0.3642 (4)	1.0690 (2)	0.073 (1)
C27	0.1849 (3)	−0.3335 (3)	1.0592 (2)	0.0551 (9)
C28	0.2866 (2)	−0.1620 (3)	0.8705 (2)	0.0392 (7)
C29	0.2862 (2)	−0.1043 (3)	0.7903 (2)	0.0359 (6)
C30	0.2479 (3)	−0.1665 (3)	0.7140 (2)	0.0466 (7)
C31	0.2569 (3)	−0.1215 (3)	0.6358 (2)	0.0525 (8)
C32	0.3071 (3)	−0.0153 (3)	0.6325 (2)	0.0482 (8)
C33	0.3458 (2)	0.0479 (3)	0.7053 (2)	0.0403 (7)
C34	0.3326 (2)	0.0072 (3)	0.7858 (2)	0.0337 (6)
H8	0.4903	0.4035	1.0213	0.0669*
H9	0.5504	0.4948	1.1523	0.0797*
H10	0.5522	0.3942	1.2802	0.0824*
H11	0.4907	0.2039	1.2768	0.0632*
H13	0.4414	0.0256	1.2042	0.0469*
H14	0.4518	−0.1565	1.0955	0.0426*
H16	0.2474	−0.0631	1.1954	0.0675*
H17	0.2211	−0.1384	1.3256	0.0951*
H18	0.3176	−0.2942	1.3902	0.1169*
H19	0.4427	−0.3749	1.3271	0.1226*
H20	0.4767	−0.2980	1.1985	0.0802*
H21	0.3444	−0.2624	1.0105	0.0412*
H23	0.1367	−0.0626	1.0013	0.0748*
H24	−0.0258	−0.1164	1.0225	0.0938*
H25	−0.0588	−0.3057	1.0596	0.0915*
H26	0.0725	−0.4419	1.0863	0.0869*
H27	0.2386	−0.3903	1.0701	0.0661*
H28	0.2670	−0.2427	0.8688	0.0467*
H30	0.2147	−0.2417	0.7170	0.0558*
H31	0.2290	−0.1630	0.5849	0.0630*
H32	0.3147	0.0148	0.5782	0.0583*
H33	0.3825	0.1193	0.7013	0.0490*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0361 (3)	0.0304 (2)	0.0312 (2)	−0.0022 (2)	0.0104 (2)	0.0012 (2)
O2	0.041 (1)	0.047 (1)	0.059 (1)	0.0074 (10)	0.015 (1)	0.006 (1)
O3	0.055 (1)	0.037 (1)	0.036 (1)	−0.0110 (9)	0.0131 (9)	−0.0030 (9)
O4	0.042 (1)	0.036 (1)	0.0299 (9)	−0.0072 (9)	0.0093 (8)	−0.0009 (9)
N5	0.032 (1)	0.034 (1)	0.035 (1)	−0.0009 (10)	0.0080 (10)	0.002 (1)
N6	0.036 (1)	0.032 (1)	0.035 (1)	−0.0019 (10)	0.0134 (10)	0.0014 (10)
C7	0.040 (2)	0.037 (2)	0.043 (2)	−0.002 (1)	0.013 (1)	−0.007 (1)
C8	0.075 (2)	0.037 (2)	0.057 (2)	−0.010 (2)	0.020 (2)	−0.006 (2)
C9	0.086 (3)	0.044 (2)	0.070 (3)	−0.013 (2)	0.022 (2)	−0.020 (2)
C10	0.077 (3)	0.063 (2)	0.060 (2)	−0.009 (2)	0.007 (2)	−0.026 (2)
C11	0.059 (2)	0.059 (2)	0.041 (2)	−0.004 (2)	0.008 (1)	−0.011 (2)
C12	0.037 (2)	0.043 (2)	0.037 (2)	0.001 (1)	0.008 (1)	−0.004 (1)
C13	0.038 (1)	0.046 (2)	0.033 (1)	0.002 (1)	0.009 (1)	0.005 (1)
C14	0.030 (1)	0.037 (2)	0.040 (2)	0.002 (1)	0.010 (1)	0.008 (1)
C15	0.043 (2)	0.048 (2)	0.037 (2)	−0.011 (1)	0.001 (1)	0.012 (1)
C16	0.049 (2)	0.079 (3)	0.043 (2)	−0.012 (2)	0.013 (2)	0.006 (2)
C17	0.072 (3)	0.123 (4)	0.049 (2)	−0.038 (3)	0.022 (2)	0.002 (3)
C18	0.115 (4)	0.126 (5)	0.049 (3)	−0.045 (4)	0.008 (3)	0.031 (3)
C19	0.124 (4)	0.097 (4)	0.070 (3)	−0.011 (3)	−0.005 (3)	0.052 (3)
C20	0.076 (3)	0.059 (2)	0.059 (2)	0.001 (2)	0.002 (2)	0.019 (2)
C21	0.039 (2)	0.030 (1)	0.036 (1)	−0.001 (1)	0.012 (1)	0.005 (1)
C22	0.043 (2)	0.047 (2)	0.032 (1)	−0.015 (1)	0.010 (1)	0.000 (1)
C23	0.040 (2)	0.072 (3)	0.076 (3)	−0.005 (2)	0.016 (2)	0.021 (2)
C24	0.038 (2)	0.114 (4)	0.077 (3)	−0.009 (2)	0.014 (2)	0.020 (3)
C25	0.048 (2)	0.128 (4)	0.052 (2)	−0.037 (3)	0.011 (2)	0.007 (2)
C26	0.096 (3)	0.079 (3)	0.051 (2)	−0.049 (3)	0.030 (2)	−0.004 (2)
C27	0.073 (2)	0.051 (2)	0.046 (2)	−0.022 (2)	0.021 (2)	−0.004 (2)
C28	0.041 (2)	0.031 (1)	0.046 (2)	−0.009 (1)	0.012 (1)	−0.004 (1)
C29	0.039 (2)	0.036 (1)	0.034 (1)	−0.001 (1)	0.008 (1)	−0.003 (1)
C30	0.057 (2)	0.037 (2)	0.043 (2)	−0.008 (1)	0.006 (1)	−0.007 (1)
C31	0.069 (2)	0.050 (2)	0.035 (2)	0.004 (2)	0.002 (2)	−0.011 (1)
C32	0.064 (2)	0.049 (2)	0.032 (2)	0.011 (2)	0.010 (1)	0.002 (1)
C33	0.047 (2)	0.040 (2)	0.035 (1)	0.004 (1)	0.011 (1)	0.003 (1)
C34	0.032 (1)	0.036 (1)	0.034 (1)	0.003 (1)	0.009 (1)	−0.001 (1)

Geometric parameters (Å, º) top

V1—O2	1.599 (2)	C17—H17	0.948
V1—O3	1.921 (2)	C18—C19	1.353 (9)
V1—O4	1.926 (2)	C18—H18	0.951
V1—N5	2.053 (2)	C19—C20	1.401 (7)
V1—N6	2.056 (2)	C19—H19	0.943
O3—C7	1.323 (4)	C20—H20	0.947
O4—C34	1.323 (3)	C21—C22	1.524 (4)
N5—C13	1.295 (4)	C21—H21	0.948
N5—C14	1.496 (4)	C22—C23	1.373 (5)
N6—C21	1.491 (4)	C22—C27	1.386 (5)
N6—C28	1.288 (4)	C23—C24	1.388 (6)
C7—C8	1.407 (4)	C23—H23	0.953
C7—C12	1.405 (4)	C24—C25	1.346 (8)
C8—C9	1.383 (5)	C24—H24	0.949
C8—H8	0.952	C25—C26	1.359 (7)
C9—C10	1.382 (6)	C25—H25	0.950
C9—H9	0.952	C26—C27	1.398 (6)
C10—C11	1.363 (6)	C26—H26	0.950
C10—H10	0.950	C27—H27	0.951
C11—C12	1.409 (4)	C28—C29	1.436 (4)
C11—H11	0.950	C28—H28	0.950
C12—C13	1.437 (4)	C29—C30	1.413 (4)
C13—H13	0.948	C29—C34	1.415 (4)
C14—C15	1.513 (4)	C30—C31	1.373 (5)
C14—C21	1.549 (4)	C30—H30	0.966
C14—H14	0.952	C31—C32	1.382 (5)
C15—C16	1.386 (5)	C31—H31	0.950
C15—C20	1.377 (5)	C32—C33	1.376 (4)
C16—C17	1.389 (6)	C32—H32	0.954
C16—H16	0.952	C33—C34	1.406 (4)
C17—C18	1.364 (8)	C33—H33	0.953

O2—V1—O3	106.7 (1)	C17—C18—C19	119.7 (5)
O2—V1—O4	110.71 (10)	C17—C18—H18	119.8
O2—V1—N5	107.8 (1)	C19—C18—H18	120.4
O2—V1—N6	104.3 (1)	C18—C19—C20	120.8 (5)
O3—V1—O4	85.66 (8)	C18—C19—H19	118.9
O3—V1—N5	88.22 (9)	C20—C19—H19	120.3
O3—V1—N6	148.74 (9)	C15—C20—C19	119.7 (4)
O4—V1—N5	141.13 (9)	C15—C20—H20	120.3
O4—V1—N6	87.12 (9)	C19—C20—H20	120.0
N5—V1—N6	78.62 (9)	N6—C21—C14	107.7 (2)
V1—O3—C7	127.9 (2)	N6—C21—C22	111.5 (2)
V1—O4—C34	128.0 (2)	N6—C21—H21	106.8
V1—N5—C13	123.9 (2)	C14—C21—C22	116.5 (2)
V1—N5—C14	118.2 (2)	C14—C21—H21	106.7
C13—N5—C14	117.4 (2)	C22—C21—H21	107.1
V1—N6—C21	117.7 (2)	C21—C22—C23	123.1 (3)
V1—N6—C28	124.1 (2)	C21—C22—C27	118.6 (3)
C21—N6—C28	117.8 (2)	C23—C22—C27	118.4 (3)
O3—C7—C8	118.6 (3)	C22—C23—C24	120.6 (4)
O3—C7—C12	122.6 (3)	C22—C23—H23	119.9
C8—C7—C12	118.7 (3)	C24—C23—H23	119.5
C7—C8—C9	120.4 (3)	C23—C24—C25	120.8 (4)
C7—C8—H8	119.6	C23—C24—H24	119.6
C9—C8—H8	120.0	C25—C24—H24	119.6
C8—C9—C10	121.1 (3)	C24—C25—C26	119.9 (4)
C8—C9—H9	119.6	C24—C25—H25	120.1
C10—C9—H9	119.3	C26—C25—H25	120.0
C9—C10—C11	119.0 (4)	C25—C26—C27	120.5 (4)
C9—C10—H10	120.7	C25—C26—H26	119.8
C11—C10—H10	120.3	C27—C26—H26	119.7
C10—C11—C12	122.1 (3)	C22—C27—C26	119.8 (3)
C10—C11—H11	119.2	C22—C27—H27	120.2
C12—C11—H11	118.7	C26—C27—H27	119.9
C7—C12—C11	118.7 (3)	N6—C28—C29	125.8 (3)
C7—C12—C13	122.6 (3)	N6—C28—H28	116.9
C11—C12—C13	118.3 (3)	C29—C28—H28	117.3
N5—C13—C12	126.0 (3)	C28—C29—C30	118.6 (3)
N5—C13—H13	116.9	C28—C29—C34	121.7 (2)
C12—C13—H13	117.1	C30—C29—C34	119.4 (3)
N5—C14—C15	115.6 (2)	C29—C30—C31	121.1 (3)
N5—C14—C21	109.6 (2)	C29—C30—H30	119.4
N5—C14—H14	106.0	C31—C30—H30	119.6
C15—C14—C21	113.2 (2)	C30—C31—C32	119.0 (3)
C15—C14—H14	105.6	C30—C31—H31	120.2
C21—C14—H14	106.0	C32—C31—H31	120.7
C14—C15—C16	122.5 (3)	C31—C32—C33	121.8 (3)
C14—C15—C20	118.3 (3)	C31—C32—H32	118.8
C16—C15—C20	119.2 (3)	C33—C32—H32	119.4
C15—C16—C17	119.8 (4)	C32—C33—C34	120.4 (3)
C15—C16—H16	120.3	C32—C33—H33	119.9
C17—C16—H16	119.9	C34—C33—H33	119.7
C16—C17—C18	120.7 (5)	O4—C34—C29	122.9 (3)
C16—C17—H17	119.7	O4—C34—C33	118.8 (3)
C18—C17—H17	119.6	C29—C34—C33	118.2 (2)

(endo) top

Crystal data top

[VO(C₂₈H₂₂N₂O₂)]	D_x = 1.342 Mg m⁻³
M_r = 485.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
Hall symbol: -P 2ac 2ab	θ = 13.4–14.9°
a = 17.671 (6) Å	µ = 0.45 mm⁻¹
b = 21.635 (7) Å	T = 297 K
c = 12.565 (4) Å	Prismatic, green
V = 4803 (2) Å³	0.7 × 0.5 × 0.2 mm
Z = 8

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.024
θ–2θ scans	θ_max = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −8→22
T_min = 0.787, T_max = 0.912	k = −10→28
5807 measured reflections	l = −6→16
5516 independent reflections	3 standard reflections every 150 reflections
4206 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.055	w = 1/[σ²(F_o²) + (0.0776P)² + 11.0899P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.193	(Δ/σ)_max = 0.0001
S = 1.04	Δρ_max = 0.75 e Å⁻³
5516 reflections	Δρ_min = −0.83 e Å⁻³
307 parameters

Crystal data top

[VO(C₂₈H₂₂N₂O₂)]	V = 4803 (2) Å³
M_r = 485.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.671 (6) Å	µ = 0.45 mm⁻¹
b = 21.635 (7) Å	T = 297 K
c = 12.565 (4) Å	0.7 × 0.5 × 0.2 mm

Data collection top

Rigaku AFC-7R diffractometer	4206 reflections with I > 2σ(I)
Absorption correction: integration (Coppens et al., 1965)	R_int = 0.024
T_min = 0.787, T_max = 0.912	3 standard reflections every 150 reflections
5807 measured reflections	intensity decay: none
5516 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H-atom parameters not refined
wR(F²) = 0.193	w = 1/[σ²(F_o²) + (0.0776P)² + 11.0899P] where P = (F_o² + 2F_c²)/3
S = 1.04	Δρ_max = 0.75 e Å⁻³
5516 reflections	Δρ_min = −0.83 e Å⁻³
307 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
V1	−0.92040 (3)	−0.17586 (3)	−0.48936 (4)	0.0330 (2)
O2	−0.8451 (2)	−0.1398 (1)	−0.4589 (3)	0.0572 (7)
O3	−0.9683 (2)	−0.1413 (1)	−0.6129 (2)	0.0516 (7)
O4	−0.8897 (1)	−0.2458 (1)	−0.5762 (2)	0.0414 (5)
N5	−1.0022 (2)	−0.1306 (1)	−0.3990 (2)	0.0339 (6)
N6	−0.9419 (2)	−0.2392 (1)	−0.3710 (2)	0.0363 (6)
C7	−1.0168 (2)	−0.0947 (2)	−0.6239 (3)	0.0416 (8)
C8	−1.0346 (3)	−0.0739 (2)	−0.7269 (3)	0.065 (1)
C9	−1.0846 (3)	−0.0262 (2)	−0.7422 (3)	0.063 (1)
C10	−1.1205 (3)	0.0028 (2)	−0.6577 (3)	0.0528 (9)
C11	−1.1044 (2)	−0.0172 (2)	−0.5566 (3)	0.0459 (8)
C12	−1.0540 (2)	−0.0663 (2)	−0.5378 (3)	0.0361 (7)
C13	−1.0439 (2)	−0.0859 (2)	−0.4295 (3)	0.0389 (7)
C14	−0.9944 (2)	−0.1489 (2)	−0.2855 (2)	0.0375 (7)
C15	−1.0483 (2)	−0.1208 (2)	−0.2056 (3)	0.0410 (7)
C16	−1.0180 (3)	−0.0947 (2)	−0.1144 (3)	0.0534 (10)
C17	−1.0641 (3)	−0.0737 (2)	−0.0340 (4)	0.069 (1)
C18	−1.1416 (3)	−0.0778 (2)	−0.0440 (4)	0.072 (1)
C19	−1.1732 (3)	−0.1029 (2)	−0.1338 (4)	0.065 (1)
C20	−1.1266 (2)	−0.1245 (2)	−0.2152 (3)	0.0502 (9)
C21	−0.9945 (2)	−0.2205 (2)	−0.2845 (2)	0.0378 (7)
C22	−1.0707 (2)	−0.2503 (2)	−0.2991 (3)	0.0410 (7)
C23	−1.1088 (3)	−0.2724 (2)	−0.2108 (4)	0.064 (1)
C24	−1.1801 (3)	−0.2991 (3)	−0.2207 (5)	0.082 (2)
C25	−1.2145 (3)	−0.3031 (3)	−0.3188 (5)	0.077 (1)
C26	−1.1775 (3)	−0.2826 (2)	−0.4061 (4)	0.067 (1)
C27	−1.1059 (2)	−0.2560 (2)	−0.3973 (3)	0.0528 (9)
C28	−0.9122 (2)	−0.2939 (2)	−0.3628 (3)	0.0403 (7)
C29	−0.8676 (2)	−0.3236 (2)	−0.4435 (3)	0.0407 (7)
C30	−0.8370 (2)	−0.3823 (2)	−0.4196 (4)	0.055 (1)
C31	−0.7982 (3)	−0.4153 (2)	−0.4944 (5)	0.064 (1)
C32	−0.7892 (2)	−0.3908 (2)	−0.5964 (4)	0.061 (1)
C33	−0.8198 (2)	−0.3340 (2)	−0.6227 (3)	0.0488 (9)
C34	−0.8601 (2)	−0.2990 (2)	−0.5471 (3)	0.0388 (7)
H8	−1.0115	−0.0932	−0.7871	0.0744*
H9	−1.0954	−0.0125	−0.8125	0.0737*
H10	−1.1546	0.0358	−0.6693	0.0620*
H11	−1.1289	0.0018	−0.4980	0.0532*
H13	−1.0710	−0.0640	−0.3762	0.0444*
H14	−0.9451	−0.1366	−0.2642	0.0424*
H16	−0.9639	−0.0912	−0.1078	0.0618*
H17	−1.0428	−0.0555	0.0285	0.0812*
H18	−1.1731	−0.0634	0.0117	0.0880*
H19	−1.2268	−0.1057	−0.1410	0.0778*
H20	−1.1482	−0.1417	−0.2776	0.0598*
H21	−0.9739	−0.2338	−0.2187	0.0433*
H23	−1.0853	−0.2698	−0.1428	0.0747*
H24	−1.2057	−0.3140	−0.1594	0.0969*
H25	−1.2642	−0.3197	−0.3236	0.0890*
H26	−1.2009	−0.2865	−0.4745	0.0789*
H27	−1.0805	−0.2411	−0.4614	0.0633*
H28	−0.9213	−0.3159	−0.2989	0.0480*
H30	−0.8435	−0.3993	−0.3503	0.0660*
H31	−0.7772	−0.4542	−0.4765	0.0746*
H32	−0.7618	−0.4137	−0.6490	0.0731*
H33	−0.8133	−0.3184	−0.6932	0.0577*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0307 (3)	0.0361 (3)	0.0323 (3)	0.0024 (2)	0.0020 (2)	−0.0042 (2)
O2	0.039 (1)	0.055 (2)	0.077 (2)	−0.005 (1)	0.005 (1)	−0.021 (1)
O3	0.073 (2)	0.051 (1)	0.031 (1)	0.026 (1)	0.004 (1)	0.000 (1)
O4	0.046 (1)	0.043 (1)	0.035 (1)	0.008 (1)	0.000 (1)	−0.006 (1)
N5	0.038 (1)	0.037 (1)	0.026 (1)	0.001 (1)	−0.001 (1)	−0.003 (1)
N6	0.035 (1)	0.042 (1)	0.032 (1)	0.005 (1)	−0.001 (1)	−0.001 (1)
C7	0.052 (2)	0.038 (2)	0.035 (2)	0.005 (2)	0.000 (1)	0.000 (1)
C8	0.103 (4)	0.059 (2)	0.034 (2)	0.031 (3)	0.006 (2)	0.004 (2)
C9	0.095 (4)	0.048 (2)	0.044 (2)	0.020 (2)	−0.005 (2)	0.011 (2)
C10	0.057 (2)	0.047 (2)	0.055 (2)	0.014 (2)	−0.006 (2)	0.005 (2)
C11	0.049 (2)	0.043 (2)	0.045 (2)	0.010 (2)	0.002 (2)	−0.001 (2)
C12	0.039 (2)	0.033 (2)	0.036 (2)	−0.001 (1)	−0.001 (1)	0.000 (1)
C13	0.044 (2)	0.041 (2)	0.032 (2)	0.002 (1)	0.003 (1)	−0.007 (1)
C14	0.041 (2)	0.046 (2)	0.025 (1)	0.006 (1)	−0.003 (1)	−0.004 (1)
C15	0.046 (2)	0.044 (2)	0.033 (2)	0.007 (2)	0.005 (1)	−0.001 (1)
C16	0.073 (3)	0.052 (2)	0.035 (2)	0.004 (2)	0.001 (2)	−0.005 (2)
C17	0.097 (4)	0.068 (3)	0.042 (2)	0.009 (3)	0.012 (2)	−0.014 (2)
C18	0.096 (4)	0.068 (3)	0.053 (3)	0.022 (3)	0.036 (3)	−0.002 (2)
C19	0.060 (3)	0.060 (3)	0.076 (3)	0.016 (2)	0.025 (2)	0.011 (2)
C20	0.048 (2)	0.052 (2)	0.051 (2)	0.009 (2)	0.005 (2)	−0.003 (2)
C21	0.040 (2)	0.047 (2)	0.026 (1)	0.009 (1)	−0.002 (1)	0.000 (1)
C22	0.041 (2)	0.042 (2)	0.040 (2)	0.006 (2)	0.003 (1)	0.000 (1)
C23	0.060 (3)	0.079 (3)	0.051 (2)	0.000 (2)	0.008 (2)	0.016 (2)
C24	0.060 (3)	0.088 (4)	0.097 (4)	−0.008 (3)	0.023 (3)	0.021 (3)
C25	0.045 (2)	0.072 (3)	0.112 (5)	−0.007 (2)	−0.002 (3)	0.001 (3)
C26	0.057 (3)	0.065 (3)	0.078 (3)	−0.003 (2)	−0.013 (2)	−0.017 (2)
C27	0.053 (2)	0.060 (2)	0.045 (2)	−0.003 (2)	−0.003 (2)	−0.009 (2)
C28	0.039 (2)	0.041 (2)	0.041 (2)	0.003 (1)	−0.004 (1)	0.003 (1)
C29	0.034 (2)	0.037 (2)	0.052 (2)	0.003 (1)	−0.004 (1)	−0.005 (1)
C30	0.052 (2)	0.045 (2)	0.067 (3)	0.009 (2)	−0.001 (2)	0.005 (2)
C31	0.052 (2)	0.038 (2)	0.102 (4)	0.009 (2)	0.008 (2)	−0.002 (2)
C32	0.048 (2)	0.045 (2)	0.091 (3)	0.004 (2)	0.014 (2)	−0.018 (2)
C33	0.039 (2)	0.050 (2)	0.057 (2)	0.001 (2)	0.008 (2)	−0.012 (2)
C34	0.027 (1)	0.044 (2)	0.045 (2)	0.001 (1)	−0.003 (1)	−0.007 (2)

Geometric parameters (Å, º) top

V1—O2	1.590 (3)	C17—H17	0.956
V1—O3	1.920 (3)	C18—C19	1.372 (7)
V1—O4	1.942 (3)	C18—H18	0.946
V1—N5	2.082 (3)	C19—C20	1.393 (7)
V1—N6	2.058 (3)	C19—H19	0.953
O3—C7	1.331 (5)	C20—H20	0.948
O4—C34	1.317 (4)	C21—C22	1.506 (5)
N5—C13	1.277 (4)	C21—H21	0.948
N5—C14	1.487 (4)	C22—C23	1.382 (6)
N6—C21	1.486 (4)	C22—C27	1.387 (6)
N6—C28	1.299 (4)	C23—C24	1.390 (7)
C7—C8	1.406 (5)	C23—H23	0.952
C7—C12	1.406 (5)	C24—C25	1.376 (9)
C8—C9	1.372 (7)	C24—H24	0.950
C8—H8	0.956	C25—C26	1.351 (8)
C9—C10	1.387 (6)	C25—H25	0.951
C9—H9	0.951	C26—C27	1.395 (7)
C10—C11	1.372 (6)	C26—H26	0.958
C10—H10	0.947	C27—H27	0.975
C11—C12	1.405 (5)	C28—C29	1.436 (5)
C11—H11	0.948	C28—H28	0.946
C12—C13	1.437 (5)	C29—C30	1.413 (5)
C13—H13	0.950	C29—C34	1.412 (5)
C14—C15	1.512 (5)	C30—C31	1.365 (7)
C14—C21	1.549 (5)	C30—H30	0.952
C14—H14	0.950	C31—C32	1.396 (8)
C15—C16	1.385 (5)	C31—H31	0.947
C15—C20	1.390 (6)	C32—C33	1.383 (6)
C16—C17	1.375 (7)	C32—H32	0.957
C16—H16	0.962	C33—C34	1.409 (5)
C17—C18	1.377 (9)	C33—H33	0.954

O2—V1—O3	111.9 (1)	C17—C18—C19	120.3 (5)
O2—V1—O4	106.5 (1)	C17—C18—H18	119.8
O2—V1—N5	102.7 (1)	C19—C18—H18	119.9
O2—V1—N6	107.9 (1)	C18—C19—C20	119.7 (5)
O3—V1—O4	88.4 (1)	C18—C19—H19	120.5
O3—V1—N5	87.2 (1)	C20—C19—H19	119.7
O3—V1—N6	139.7 (1)	C15—C20—C19	120.3 (4)
O4—V1—N5	150.0 (1)	C15—C20—H20	119.7
O4—V1—N6	86.5 (1)	C19—C20—H20	120.0
N5—V1—N6	77.9 (1)	N6—C21—C14	105.4 (3)
V1—O3—C7	131.5 (2)	N6—C21—C22	110.7 (3)
V1—O4—C34	129.5 (2)	N6—C21—H21	108.3
V1—N5—C13	126.4 (2)	C14—C21—C22	115.4 (3)
V1—N5—C14	109.6 (2)	C14—C21—H21	108.1
C13—N5—C14	122.9 (3)	C22—C21—H21	108.6
V1—N6—C21	117.6 (2)	C21—C22—C23	119.1 (3)
V1—N6—C28	126.1 (2)	C21—C22—C27	123.2 (3)
C21—N6—C28	116.3 (3)	C23—C22—C27	117.8 (4)
O3—C7—C8	118.8 (3)	C22—C23—C24	120.8 (4)
O3—C7—C12	123.5 (3)	C22—C23—H23	119.1
C8—C7—C12	117.6 (4)	C24—C23—H23	120.1
C7—C8—C9	120.9 (4)	C23—C24—C25	120.4 (5)
C7—C8—H8	119.6	C23—C24—H24	120.0
C9—C8—H8	119.5	C25—C24—H24	119.6
C8—C9—C10	121.8 (4)	C24—C25—C26	119.5 (5)
C8—C9—H9	119.6	C24—C25—H25	119.2
C10—C9—H9	118.6	C26—C25—H25	121.3
C9—C10—C11	118.1 (4)	C25—C26—C27	120.7 (5)
C9—C10—H10	121.0	C25—C26—H26	119.3
C11—C10—H10	120.9	C27—C26—H26	120.0
C10—C11—C12	121.7 (4)	C22—C27—C26	120.8 (4)
C10—C11—H11	119.1	C22—C27—H27	120.0
C12—C11—H11	119.2	C26—C27—H27	119.2
C7—C12—C11	119.8 (3)	N6—C28—C29	124.9 (3)
C7—C12—C13	122.8 (3)	N6—C28—H28	117.1
C11—C12—C13	117.4 (3)	C29—C28—H28	117.9
N5—C13—C12	125.5 (3)	C28—C29—C30	117.5 (3)
N5—C13—H13	117.3	C28—C29—C34	122.3 (3)
C12—C13—H13	117.2	C30—C29—C34	119.9 (3)
N5—C14—C15	118.2 (3)	C29—C30—C31	121.1 (4)
N5—C14—C21	105.8 (2)	C29—C30—H30	119.7
N5—C14—H14	106.3	C31—C30—H30	119.2
C15—C14—C21	113.3 (3)	C30—C31—C32	119.4 (4)
C15—C14—H14	106.3	C30—C31—H31	119.9
C21—C14—H14	106.1	C32—C31—H31	120.7
C14—C15—C16	118.0 (3)	C31—C32—C33	120.9 (4)
C14—C15—C20	123.1 (3)	C31—C32—H32	119.7
C16—C15—C20	118.7 (4)	C33—C32—H32	119.4
C15—C16—C17	120.8 (4)	C32—C33—C34	120.9 (4)
C15—C16—H16	119.2	C32—C33—H33	119.3
C17—C16—H16	120.0	C34—C33—H33	119.7
C16—C17—C18	120.1 (4)	O4—C34—C29	123.2 (3)
C16—C17—H17	120.4	O4—C34—C33	118.9 (3)
C18—C17—H17	119.5	C29—C34—C33	117.8 (3)

Experimental details

	(exo)	(endo)
Crystal data
Chemical formula	[VO(C₂₈H₂₂N₂O₂)]	[VO(C₂₈H₂₂N₂O₂)]
M_r	485.43	485.43
Crystal system, space group	Monoclinic, P2₁/n	Orthorhombic, Pbca
Temperature (K)	297	297
a, b, c (Å)	13.278 (2), 11.340 (3), 15.940 (2)	17.671 (6), 21.635 (7), 12.565 (4)
α, β, γ (°)	90, 101.12 (1), 90	90, 90, 90
V (Å³)	2355.1 (7)	4803 (2)
Z	4	8
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.45	0.45
Crystal size (mm)	0.7 × 0.2 × 0.2	0.7 × 0.5 × 0.2

Data collection
Diffractometer	Rigaku AFC-7R diffractometer	Rigaku AFC-7R diffractometer
Absorption correction	Integration (Coppens et al., 1965)	Integration (Coppens et al., 1965)
T_min, T_max	0.881, 0.915	0.787, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	5646, 5417, 3380	5807, 5516, 4206
R_int	0.016	0.024
(sin θ/λ)_max (Å⁻¹)	0.650	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.03	0.055, 0.193, 1.04
No. of reflections	5417	5516
No. of parameters	307	307
No. of restraints	?	?
H-atom treatment	H-atom parameters not refined	H-atom parameters not refined
	w = 1/[σ²(F_o²) + (0.0505P)² + 1.8247P] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0776P)² + 11.0899P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.33	0.75, −0.83

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), TEXSAN.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

The exo and endo isomers of [N,N'-bis­(salicyl­idene)-1,2-di­phenyl-(RS,SR)-1,2-ethane­diyl­diamin­ato]­oxo­vanadium(IV)

Supporting information

The exo and endo isomers of [N,N'-bis(salicylidene)-1,2-diphenyl-(RS,SR)-1,2-ethanediyldiaminato]oxovanadium(IV)