The first oxazoline adduct of Zn(acac)(2): bis-(acetyl-acetonato-κO,O')(2-phenyl-2-oxazoline-κN)zinc(II).

The title material, [Zn(C(5)H(7)O(2))(2)(C(9)H(9)NO)], was synthesized by the treatment of bis-(acetyl-acetonato)zinc(II) monohydrate with 2-phenyl-2-oxazoline. The Zn atom is coordinated by two chelating acetyl-acetonate groups and one oxazoline ligand in the apical position of a slightly distorted square-pyramidal metal-ligand geometry.

Related literature

For general background, see: Addison et al. (1984 ▶); Itoh et al. (1989 ▶); Kaeriyama (1974 ▶); Williams (1989 ▶). For related structures, see: Barclay et al. (2003 ▶); Brahma et al. (2008 ▶); Decken et al. (2006 ▶); Fronczek et al. (1990 ▶); Gossage & Jenkins (2008 ▶); Gossage et al. (2009 ▶); Hamid et al. (2005 ▶); Qian et al. (2006 ▶).

Experimental

Crystal data

[Zn(C5H7O2)2(C9H9NO)]

M = 410.77

Orthorhombic,

a = 9.5009 (3) Å

b = 14.1674 (4) Å

c = 14.2407 (5) Å

V = 1916.84 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.03 mm−1

T = 200 (2) K

0.28 × 0.15 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: refined from ΔF (Parkin et al., 1995 ▶) T min = 0.542, T max = 0.859

8596 measured reflections

3600 independent reflections

3466 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.080

S = 1.05

3600 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: DIRDIF96 (Beurskens et al., 1996 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: EUCLID (Spek, 1982 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042712/kj2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042712/kj2105Isup2.hkl

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

[Zn(C5H7O2)2(C9H9NO)]	F(000) = 856
Mr = 410.77	Dx = 1.430 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1999 reflections
a = 9.5009 (3) Å	θ = 4.4–69.6°
b = 14.1674 (4) Å	µ = 2.03 mm−1
c = 14.2407 (5) Å	T = 200 K
V = 1916.84 (11) Å3	Blocks, white
Z = 4	0.28 × 0.15 × 0.08 mm

Nonius KappaCCD diffractometer	3600 independent reflections
Radiation source: fine-focus sealed tube	3466 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.035
Detector resolution: 9 pixels mm-1	θmax = 69.6°, θmin = 4.4°
φ and ω scans	h = −11→11
Absorption correction: part of the refinement model (ΔF) (Parkin et al., 1995)	k = −17→17
Tmin = 0.542, Tmax = 0.859	l = −17→17
8596 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.5913P] where P = (Fo2 + 2Fc2)/3
3600 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3
0 constraints

Experimental. Absorption correction: Parkin et al., 1995. Cubic fit to sin(θ)/λ; 24 parameters 1H NMR [300 MHz: CDCl3]: δH (vs. TMS) = 1.87 [s, 12H, –CH3], 4.03 [t, J = 11.7 Hz, 2H, –CH2N], 4.48 [t, 2H, –CH2O], 5.26 [s, 2H, –CH], 7.38 [m, 4H, ArH], 7.85 [d, J = 8.8 Hz,1H, ArH]; 13C{1H}NMR (75 MHz; CDCl3): δC (vs. TMS) = 28.1, 53.7, 68.2, 99.9, 125.9, 128.2, 129.0, 132.0, 165.0(w), 193.1).

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
C1	0.3061 (3)	−0.0086 (3)	−0.06798 (17)	0.0483 (7)
H1A	0.2514	0.0460	−0.0870	0.058*
H1B	0.2575	−0.0654	−0.0879	0.058*
C2	0.4526 (3)	−0.0046 (2)	−0.10858 (16)	0.0433 (6)
H2A	0.4650	−0.0522	−0.1569	0.052*
H2B	0.4720	0.0570	−0.1352	0.052*
C3	0.4621 (2)	−0.01785 (18)	0.04907 (15)	0.0316 (5)
C4	0.5407 (3)	−0.02065 (17)	0.13820 (16)	0.0319 (5)
C5	0.6862 (3)	−0.01280 (19)	0.13607 (17)	0.0374 (5)
H5	0.7331	−0.0086	0.0789	0.045*
C6	0.7613 (3)	−0.0112 (2)	0.21951 (18)	0.0430 (6)
H6	0.8589	−0.0061	0.2181	0.052*
C7	0.6925 (3)	−0.0173 (2)	0.30468 (18)	0.0406 (6)
H7	0.7435	−0.0149	0.3604	0.049*
C8	0.5487 (3)	−0.0269 (2)	0.30720 (18)	0.0418 (6)
H8	0.5027	−0.0317	0.3646	0.050*
C9	0.4715 (3)	−0.02941 (19)	0.22414 (18)	0.0378 (6)
H9	0.3743	−0.0369	0.2260	0.045*
C10	−0.1142 (4)	−0.2000 (3)	−0.0308 (2)	0.0620 (9)
H10A	−0.1390	−0.1528	−0.0763	0.093*
H10B	−0.1980	−0.2232	−0.0010	0.093*
H10C	−0.0667	−0.2512	−0.0616	0.093*
C11	−0.0186 (3)	−0.1573 (2)	0.0420 (2)	0.0426 (6)
C12	0.0308 (3)	−0.21237 (19)	0.1148 (2)	0.0485 (7)
H12	0.0107	−0.2766	0.1119	0.058*
C13	0.1077 (3)	−0.18128 (18)	0.1921 (2)	0.0409 (6)
C14	0.1554 (4)	−0.2508 (2)	0.2652 (2)	0.0602 (8)
H14A	0.2077	−0.2183	0.3129	0.090*
H14B	0.2141	−0.2977	0.2364	0.090*
H14C	0.0748	−0.2807	0.2929	0.090*
C15	0.0715 (4)	0.2718 (2)	−0.0305 (2)	0.0611 (9)
H15A	0.0125	0.2405	−0.0756	0.092*
H15B	0.1545	0.2951	−0.0612	0.092*
H15C	0.0210	0.3235	−0.0030	0.092*
C16	0.1131 (3)	0.20281 (19)	0.0454 (2)	0.0430 (7)
C17	0.1982 (3)	0.23396 (18)	0.1187 (2)	0.0466 (7)
H17	0.2349	0.2946	0.1139	0.056*
C18	0.2333 (3)	0.18219 (18)	0.19881 (19)	0.0407 (6)
C19	0.3242 (4)	0.2251 (2)	0.2731 (2)	0.0591 (9)
H19A	0.3384	0.1802	0.3228	0.089*
H19B	0.2791	0.2804	0.2978	0.089*
H19C	0.4135	0.2421	0.2466	0.089*
N1	0.32955 (19)	−0.00883 (16)	0.03537 (13)	0.0343 (4)
O1	0.54378 (17)	−0.02335 (15)	−0.02807 (12)	0.0415 (4)
O2	0.0063 (2)	−0.06991 (14)	0.03232 (13)	0.0445 (5)
O3	0.1428 (2)	−0.09589 (12)	0.20636 (12)	0.0397 (4)
O4	0.0640 (2)	0.12044 (14)	0.03780 (13)	0.0454 (5)
O5	0.1921 (2)	0.09787 (12)	0.21440 (13)	0.0402 (4)
Zn1	0.14228 (3)	0.00792 (2)	0.10978 (2)	0.03289 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0386 (13)	0.078 (2)	0.0279 (12)	−0.0026 (15)	−0.0031 (10)	0.0011 (15)
C2	0.0376 (12)	0.0633 (17)	0.0291 (11)	0.0052 (13)	−0.0037 (9)	0.0008 (15)
C3	0.0341 (12)	0.0299 (13)	0.0307 (11)	−0.0014 (10)	0.0023 (9)	−0.0004 (10)
C4	0.0354 (12)	0.0272 (12)	0.0331 (11)	0.0032 (10)	−0.0031 (9)	−0.0007 (9)
C5	0.0336 (12)	0.0412 (14)	0.0374 (12)	0.0001 (11)	0.0012 (9)	0.0030 (11)
C6	0.0332 (12)	0.0524 (17)	0.0435 (14)	−0.0003 (13)	−0.0040 (10)	0.0027 (14)
C7	0.0400 (13)	0.0421 (14)	0.0398 (13)	0.0048 (12)	−0.0103 (10)	−0.0032 (12)
C8	0.0427 (14)	0.0507 (17)	0.0321 (12)	0.0070 (12)	−0.0009 (10)	0.0006 (11)
C9	0.0313 (12)	0.0457 (16)	0.0365 (13)	0.0020 (11)	0.0007 (10)	−0.0022 (11)
C10	0.068 (2)	0.0600 (19)	0.0585 (19)	−0.0184 (17)	−0.0087 (16)	−0.0061 (16)
C11	0.0338 (14)	0.0421 (15)	0.0519 (16)	−0.0045 (12)	0.0040 (12)	−0.0090 (12)
C12	0.0532 (17)	0.0314 (13)	0.0610 (18)	−0.0033 (12)	−0.0049 (15)	−0.0036 (14)
C13	0.0409 (15)	0.0313 (13)	0.0505 (15)	0.0014 (11)	0.0046 (12)	0.0035 (11)
C14	0.067 (2)	0.0442 (16)	0.069 (2)	0.0031 (16)	−0.0091 (18)	0.0123 (15)
C15	0.080 (2)	0.049 (2)	0.0546 (19)	0.0087 (17)	−0.0094 (18)	0.0076 (15)
C16	0.0487 (17)	0.0333 (14)	0.0471 (16)	0.0081 (12)	0.0045 (13)	0.0025 (11)
C17	0.0545 (16)	0.0306 (13)	0.0548 (18)	−0.0056 (12)	0.0001 (14)	0.0031 (13)
C18	0.0430 (15)	0.0346 (14)	0.0446 (15)	−0.0032 (12)	0.0031 (12)	−0.0030 (11)
C19	0.073 (2)	0.0449 (17)	0.0589 (19)	−0.0137 (16)	−0.0123 (16)	−0.0033 (14)
N1	0.0333 (10)	0.0416 (11)	0.0281 (9)	−0.0003 (10)	−0.0020 (7)	−0.0012 (9)
O1	0.0335 (8)	0.0607 (13)	0.0303 (8)	0.0036 (9)	0.0014 (7)	0.0009 (8)
O2	0.0448 (11)	0.0447 (12)	0.0439 (10)	−0.0115 (9)	−0.0053 (8)	0.0031 (9)
O3	0.0431 (10)	0.0378 (9)	0.0384 (9)	−0.0065 (9)	0.0006 (9)	0.0031 (7)
O4	0.0506 (12)	0.0378 (10)	0.0478 (11)	0.0042 (9)	−0.0092 (9)	0.0004 (8)
O5	0.0517 (12)	0.0340 (9)	0.0350 (10)	−0.0027 (8)	0.0014 (8)	−0.0017 (7)
Zn1	0.03214 (17)	0.03310 (17)	0.03342 (17)	−0.00265 (14)	0.00149 (12)	0.00024 (14)

C1—N1	1.489 (3)	C11—C12	1.379 (4)
C1—C2	1.508 (3)	C12—C13	1.393 (4)
C1—H1A	0.9700	C12—H12	0.9300
C1—H1B	0.9700	C13—O3	1.271 (3)
C2—O1	1.461 (3)	C13—C14	1.503 (4)
C2—H2A	0.9700	C14—H14A	0.9600
C2—H2B	0.9700	C14—H14B	0.9600
C3—N1	1.281 (3)	C14—H14C	0.9600
C3—O1	1.347 (3)	C15—C16	1.510 (4)
C3—C4	1.473 (3)	C15—H15A	0.9600
C4—C5	1.387 (4)	C15—H15B	0.9600
C4—C9	1.395 (4)	C15—H15C	0.9600
C5—C6	1.387 (3)	C16—O4	1.261 (4)
C5—H5	0.9300	C16—C17	1.393 (4)
C6—C7	1.381 (4)	C17—C18	1.397 (4)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.373 (4)	C18—O5	1.277 (3)
C7—H7	0.9300	C18—C19	1.495 (4)
C8—C9	1.392 (4)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C9—H9	0.9300	C19—H19C	0.9600
C10—C11	1.506 (4)	N1—Zn1	2.0844 (19)
C10—H10A	0.9600	O2—Zn1	2.0253 (19)
C10—H10B	0.9600	O3—Zn1	2.0136 (17)
C10—H10C	0.9600	O4—Zn1	2.0359 (19)
C11—O2	1.268 (4)	O5—Zn1	2.0169 (18)
N1—C1—C2	103.94 (19)	C12—C13—C14	119.9 (3)
N1—C1—H1A	111.0	C13—C14—H14A	109.5
C2—C1—H1A	111.0	C13—C14—H14B	109.5
N1—C1—H1B	111.0	H14A—C14—H14B	109.5
C2—C1—H1B	111.0	C13—C14—H14C	109.5
H1A—C1—H1B	109.0	H14A—C14—H14C	109.5
O1—C2—C1	103.86 (18)	H14B—C14—H14C	109.5
O1—C2—H2A	111.0	C16—C15—H15A	109.5
C1—C2—H2A	111.0	C16—C15—H15B	109.5
O1—C2—H2B	111.0	H15A—C15—H15B	109.5
C1—C2—H2B	111.0	C16—C15—H15C	109.5
H2A—C2—H2B	109.0	H15A—C15—H15C	109.5
N1—C3—O1	116.6 (2)	H15B—C15—H15C	109.5
N1—C3—C4	129.2 (2)	O4—C16—C17	124.9 (3)
O1—C3—C4	114.17 (19)	O4—C16—C15	116.2 (3)
C5—C4—C9	119.7 (2)	C17—C16—C15	118.9 (3)
C5—C4—C3	118.9 (2)	C16—C17—C18	125.8 (2)
C9—C4—C3	121.3 (2)	C16—C17—H17	117.1
C6—C5—C4	119.7 (2)	C18—C17—H17	117.1
C6—C5—H5	120.1	O5—C18—C17	124.1 (3)
C4—C5—H5	120.1	O5—C18—C19	115.8 (3)
C7—C6—C5	120.5 (2)	C17—C18—C19	120.2 (3)
C7—C6—H6	119.7	C18—C19—H19A	109.5
C5—C6—H6	119.7	C18—C19—H19B	109.5
C8—C7—C6	120.0 (2)	H19A—C19—H19B	109.5
C8—C7—H7	120.0	C18—C19—H19C	109.5
C6—C7—H7	120.0	H19A—C19—H19C	109.5
C7—C8—C9	120.3 (2)	H19B—C19—H19C	109.5
C7—C8—H8	119.9	C3—N1—C1	107.34 (19)
C9—C8—H8	119.9	C3—N1—Zn1	140.65 (16)
C8—C9—C4	119.7 (2)	C1—N1—Zn1	112.00 (14)
C8—C9—H9	120.2	C3—O1—C2	106.74 (17)
C4—C9—H9	120.2	C11—O2—Zn1	126.22 (19)
C11—C10—H10A	109.5	C13—O3—Zn1	125.81 (17)
C11—C10—H10B	109.5	C16—O4—Zn1	123.14 (18)
H10A—C10—H10B	109.5	C18—O5—Zn1	122.33 (18)
C11—C10—H10C	109.5	O3—Zn1—O5	87.50 (7)
H10A—C10—H10C	109.5	O3—Zn1—O2	88.62 (8)
H10B—C10—H10C	109.5	O5—Zn1—O2	153.64 (8)
O2—C11—C12	124.8 (3)	O3—Zn1—O4	156.45 (8)
O2—C11—C10	115.4 (3)	O5—Zn1—O4	87.87 (8)
C12—C11—C10	119.7 (3)	O2—Zn1—O4	85.36 (8)
C11—C12—C13	126.4 (3)	O3—Zn1—N1	105.19 (8)
C11—C12—H12	116.8	O5—Zn1—N1	104.31 (8)
C13—C12—H12	116.8	O2—Zn1—N1	101.87 (8)
O3—C13—C12	124.4 (3)	O4—Zn1—N1	98.33 (8)
O3—C13—C14	115.7 (3)
N1—C1—C2—O1	11.7 (3)	C10—C11—O2—Zn1	−174.4 (2)
N1—C3—C4—C5	−167.8 (3)	C12—C13—O3—Zn1	−16.7 (4)
O1—C3—C4—C5	10.4 (4)	C14—C13—O3—Zn1	163.0 (2)
N1—C3—C4—C9	11.2 (5)	C17—C16—O4—Zn1	−17.8 (4)
O1—C3—C4—C9	−170.6 (2)	C15—C16—O4—Zn1	163.8 (2)
C9—C4—C5—C6	−1.7 (4)	C17—C18—O5—Zn1	26.4 (4)
C3—C4—C5—C6	177.3 (2)	C19—C18—O5—Zn1	−153.8 (2)
C4—C5—C6—C7	−0.1 (5)	C13—O3—Zn1—O5	174.6 (2)
C5—C6—C7—C8	1.3 (5)	C13—O3—Zn1—O2	20.7 (2)
C6—C7—C8—C9	−0.7 (5)	C13—O3—Zn1—O4	95.8 (3)
C7—C8—C9—C4	−1.0 (4)	C13—O3—Zn1—N1	−81.2 (2)
C5—C4—C9—C8	2.2 (4)	C18—O5—Zn1—O3	167.7 (2)
C3—C4—C9—C8	−176.7 (2)	C18—O5—Zn1—O2	−110.5 (2)
O2—C11—C12—C13	4.3 (5)	C18—O5—Zn1—O4	−35.4 (2)
C10—C11—C12—C13	−173.1 (3)	C18—O5—Zn1—N1	62.7 (2)
C11—C12—C13—O3	0.4 (5)	C11—O2—Zn1—O3	−16.6 (2)
C11—C12—C13—C14	−179.3 (3)	C11—O2—Zn1—O5	−98.1 (3)
O4—C16—C17—C18	−5.6 (5)	C11—O2—Zn1—O4	−173.8 (2)
C15—C16—C17—C18	172.8 (3)	C11—O2—Zn1—N1	88.7 (2)
C16—C17—C18—O5	0.8 (5)	C16—O4—Zn1—O3	110.2 (3)
C16—C17—C18—C19	−179.0 (3)	C16—O4—Zn1—O5	31.4 (2)
O1—C3—N1—C1	0.8 (4)	C16—O4—Zn1—O2	−174.1 (2)
C4—C3—N1—C1	178.9 (3)	C16—O4—Zn1—N1	−72.7 (2)
O1—C3—N1—Zn1	−177.5 (2)	C3—N1—Zn1—O3	−51.4 (3)
C4—C3—N1—Zn1	0.6 (5)	C1—N1—Zn1—O3	130.4 (2)
C2—C1—N1—C3	−8.1 (4)	C3—N1—Zn1—O5	39.9 (3)
C2—C1—N1—Zn1	170.75 (19)	C1—N1—Zn1—O5	−138.3 (2)
N1—C3—O1—C2	7.2 (3)	C3—N1—Zn1—O2	−143.2 (3)
C4—C3—O1—C2	−171.2 (2)	C1—N1—Zn1—O2	38.5 (2)
C1—C2—O1—C3	−11.5 (3)	C3—N1—Zn1—O4	129.8 (3)
C12—C11—O2—Zn1	8.1 (4)	C1—N1—Zn1—O4	−48.4 (2)

Table 1

Selected bond lengths (Å)

N1—Zn1	2.0844 (19)
O2—Zn1	2.0253 (19)
O3—Zn1	2.0136 (17)
O4—Zn1	2.0359 (19)
O5—Zn1	2.0169 (18)