(Acetone-κO){6,6'-di-tert-butyl-2,2'-[1,2-phenyl-enebis(nitrilo-methyl-idyne)]diphenolato-κO,N,N',O'}zinc(II).

The mol-ecule of the title compound, [Zn(C(28)H(30)N(2)O(2))(CH(3)COCH(3))], lies across a mirror plane with the Zn(II) ion and the acetone mol-ecule on the mirror plane. The Zn(II) ion is in a five-coordinate distorted square-pyramidal N(2)O(3) environment, with the two imine N and two phenolic O atoms of the tetra-dentate Schiff base dianion in the basal plane and the acetone mol-ecule in the apical position. The central benzene ring makes a dihedral angle of 16.5 (2)° with the two outer phenolate rings. In the crystal structure, the mol-ecules are arranged into anti-parallel columns along the a axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Eltayeb et al. (2007a ▶,b ▶,c ▶); Reglinski et al. (2002 ▶). For background to the applications of zinc complexes, see, for example: Assaf & Chung (1984 ▶); Basak et al. (2007 ▶); Berg & Shi (1996 ▶); Tarafder et al. (2002 ▶).

Experimental

Crystal data

[Zn(C28H30N2O2)(C3H6O)]

M = 550.11

Monoclinic,

a = 10.5803 (16) Å

b = 16.3602 (19) Å

c = 15.729 (2) Å

β = 94.446 (10)°

V = 2714.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.94 mm−1

T = 100.0 (1) K

0.57 × 0.24 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.616, T max = 0.935

29567 measured reflections

2756 independent reflections

2613 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.190

S = 1.20

2756 reflections

178 parameters

H-atom parameters constrained

Δρmax = 1.50 e Å−3

Δρmin = −1.15 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011215/ci2585sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011215/ci2585Isup2.hkl

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

[Zn(C28H30N2O2)(C3H6O)]	F000 = 1160
Mr = 550.11	Dx = 1.346 Mg m−3
Monoclinic, C2/m	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 2756 reflections
a = 10.5803 (16) Å	θ = 2.3–26.0º
b = 16.3602 (19) Å	µ = 0.94 mm−1
c = 15.729 (2) Å	T = 100.0 (1) K
β = 94.446 (10)º	Plate, yellow
V = 2714.4 (6) Å3	0.57 × 0.24 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2756 independent reflections
Radiation source: fine-focus sealed tube	2613 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.090
Detector resolution: 8.33 pixels mm-1	θmax = 26.0º
T = 100.0(1) K	θmin = 2.3º
ω scans	h = −13→13
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −20→20
Tmin = 0.616, Tmax = 0.935	l = −19→19
29567 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073	H-atom parameters constrained
wR(F2) = 0.190	w = 1/[σ2(Fo2) + (0.0669P)2 + 29.8359P] where P = (Fo2 + 2Fc2)/3
S = 1.20	(Δ/σ)max = 0.001
2756 reflections	Δρmax = 1.50 e Å−3
178 parameters	Δρmin = −1.15 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Zn1	0.50605 (6)	0.0000	0.18490 (4)	0.0170 (3)
O1	0.6013 (3)	0.0895 (2)	0.2409 (2)	0.0271 (8)
O2	0.3336 (4)	0.0000	0.2526 (3)	0.0231 (11)
N1	0.4250 (3)	0.0807 (3)	0.0944 (2)	0.0208 (9)
C1	0.6146 (4)	0.1649 (3)	0.2177 (3)	0.0185 (10)
C2	0.7084 (4)	0.2160 (3)	0.2638 (3)	0.0213 (10)
C3	0.7224 (5)	0.2950 (3)	0.2378 (3)	0.0264 (11)
H3A	0.7845	0.3269	0.2666	0.032*
C4	0.6474 (5)	0.3306 (4)	0.1694 (3)	0.0316 (12)
H4A	0.6589	0.3849	0.1543	0.038*
C5	0.5578 (4)	0.2836 (3)	0.1261 (3)	0.0251 (11)
H5A	0.5069	0.3064	0.0814	0.030*
C6	0.5411 (4)	0.2014 (3)	0.1477 (3)	0.0197 (10)
C7	0.4485 (4)	0.1576 (3)	0.0931 (3)	0.0186 (10)
H7A	0.4008	0.1884	0.0526	0.022*
C8	0.3366 (4)	0.0429 (3)	0.0341 (3)	0.0206 (10)
C9	0.2534 (4)	0.0848 (4)	−0.0238 (3)	0.0227 (10)
H9A	0.2520	0.1417	−0.0234	0.027*
C10	0.1733 (4)	0.0427 (4)	−0.0815 (3)	0.0260 (11)
H10A	0.1171	0.0717	−0.1217	0.031*
C11	0.7916 (4)	0.1815 (3)	0.3403 (3)	0.0230 (11)
C12	0.8813 (6)	0.2459 (5)	0.3807 (4)	0.0481 (18)
H12A	0.8329	0.2907	0.4005	0.072*
H12B	0.9361	0.2653	0.3392	0.072*
H12C	0.9314	0.2223	0.4279	0.072*
C13	0.8731 (6)	0.1118 (5)	0.3111 (4)	0.057 (2)
H13A	0.9317	0.1325	0.2727	0.086*
H13B	0.8198	0.0712	0.2825	0.086*
H13C	0.9192	0.0877	0.3598	0.086*
C14	0.7089 (5)	0.1515 (5)	0.4096 (3)	0.0411 (17)
H14A	0.6484	0.1930	0.4212	0.062*
H14B	0.7614	0.1399	0.4607	0.062*
H14C	0.6649	0.1027	0.3905	0.062*
C15	0.3125 (6)	0.0000	0.3276 (4)	0.0202 (14)
C16	0.4167 (6)	0.0000	0.3977 (4)	0.0337 (19)
H16A	0.4975	0.0000	0.3738	0.051*
H16B	0.4088	−0.0479	0.4325	0.051*
C17	0.1792 (7)	0.0000	0.3533 (5)	0.037 (2)
H17A	0.1213	0.0000	0.3031	0.055*
H17B	0.1646	−0.0479	0.3868	0.055*

	U11	U22	U33	U12	U13	U23
Zn1	0.0076 (4)	0.0354 (5)	0.0077 (4)	0.000	−0.0021 (2)	0.000
O1	0.0237 (17)	0.040 (2)	0.0163 (16)	−0.0073 (15)	−0.0093 (13)	0.0022 (15)
O2	0.013 (2)	0.041 (3)	0.015 (2)	0.000	0.0024 (17)	0.000
N1	0.0078 (16)	0.047 (3)	0.0077 (16)	−0.0002 (17)	−0.0016 (13)	−0.0003 (16)
C1	0.0103 (19)	0.035 (3)	0.0099 (19)	0.0010 (18)	0.0022 (15)	−0.0028 (18)
C2	0.0092 (19)	0.048 (3)	0.0070 (19)	−0.004 (2)	0.0026 (15)	−0.0035 (19)
C3	0.022 (2)	0.041 (3)	0.017 (2)	−0.010 (2)	−0.0006 (18)	−0.001 (2)
C4	0.032 (3)	0.045 (3)	0.018 (2)	−0.010 (2)	0.000 (2)	0.001 (2)
C5	0.022 (2)	0.042 (3)	0.012 (2)	0.000 (2)	0.0012 (17)	0.002 (2)
C6	0.0091 (19)	0.042 (3)	0.0086 (19)	−0.0013 (19)	0.0027 (15)	−0.0027 (19)
C7	0.0098 (19)	0.036 (3)	0.010 (2)	0.0016 (18)	−0.0002 (15)	0.0029 (18)
C8	0.0071 (18)	0.048 (3)	0.0069 (18)	0.0005 (19)	0.0013 (15)	−0.0008 (18)
C9	0.015 (2)	0.041 (3)	0.012 (2)	0.000 (2)	0.0003 (16)	0.0039 (19)
C10	0.015 (2)	0.050 (3)	0.012 (2)	0.004 (2)	−0.0046 (17)	0.002 (2)
C11	0.012 (2)	0.047 (3)	0.010 (2)	−0.002 (2)	0.0007 (16)	−0.002 (2)
C12	0.039 (3)	0.079 (5)	0.023 (3)	−0.027 (3)	−0.017 (2)	0.010 (3)
C13	0.037 (3)	0.112 (7)	0.021 (3)	0.041 (4)	−0.015 (2)	−0.018 (3)
C14	0.015 (2)	0.094 (5)	0.014 (2)	−0.010 (3)	−0.0021 (18)	0.015 (3)
C15	0.009 (3)	0.036 (4)	0.016 (3)	0.000	0.002 (2)	0.000
C16	0.016 (3)	0.069 (6)	0.016 (3)	0.000	−0.001 (3)	0.000
C17	0.015 (3)	0.075 (6)	0.021 (4)	0.000	0.007 (3)	0.000

Zn1—O1i	1.949 (4)	C9—C10	1.378 (7)
Zn1—O1	1.949 (4)	C9—H9A	0.93
Zn1—N1	2.078 (4)	C10—C10i	1.396 (12)
Zn1—N1i	2.078 (4)	C10—H10A	0.96
Zn1—O2	2.182 (4)	C11—C13	1.522 (8)
O1—C1	1.296 (6)	C11—C12	1.523 (8)
O2—C15	1.218 (8)	C11—C14	1.532 (6)
N1—C7	1.283 (7)	C12—H12A	0.96
N1—C8	1.420 (6)	C12—H12B	0.96
C1—C6	1.430 (6)	C12—H12C	0.96
C1—C2	1.449 (6)	C13—H13A	0.96
C2—C3	1.367 (8)	C13—H13B	0.96
C2—C11	1.541 (6)	C13—H13C	0.96
C3—C4	1.412 (7)	C14—H14A	0.96
C3—H3A	0.93	C14—H14B	0.96
C4—C5	1.362 (7)	C14—H14C	0.96
C4—H4A	0.93	C15—C17	1.497 (9)
C5—C6	1.401 (8)	C15—C16	1.498 (9)
C5—H5A	0.93	C16—H16A	0.96
C6—C7	1.442 (6)	C16—H16B	0.96
C7—H7A	0.93	C17—H17A	0.96
C8—C9	1.396 (6)	C17—H17B	0.96
C8—C8i	1.404 (11)
O1i—Zn1—O1	97.4 (2)	C10—C9—C8	120.5 (5)
O1i—Zn1—N1	163.48 (15)	C10—C9—H9A	119.7
O1—Zn1—N1	90.24 (15)	C8—C9—H9A	119.7
O1i—Zn1—N1i	90.23 (15)	C9—C10—C10i	120.0 (3)
O1—Zn1—N1i	163.48 (15)	C9—C10—H10A	120.3
N1—Zn1—N1i	78.9 (2)	C10i—C10—H10A	119.7
O1i—Zn1—O2	101.67 (13)	C13—C11—C12	107.2 (5)
O1—Zn1—O2	101.67 (13)	C13—C11—C14	110.0 (6)
N1—Zn1—O2	91.02 (13)	C12—C11—C14	107.2 (4)
N1i—Zn1—O2	91.02 (13)	C13—C11—C2	110.0 (4)
C1—O1—Zn1	130.6 (3)	C12—C11—C2	111.9 (5)
C15—O2—Zn1	134.1 (4)	C14—C11—C2	110.5 (4)
C7—N1—C8	122.3 (4)	C11—C12—H12A	109.5
C7—N1—Zn1	124.3 (3)	C11—C12—H12B	109.5
C8—N1—Zn1	113.4 (3)	H12A—C12—H12B	109.5
O1—C1—C6	123.4 (4)	C11—C12—H12C	109.5
O1—C1—C2	119.6 (4)	H12A—C12—H12C	109.5
C6—C1—C2	117.0 (4)	H12B—C12—H12C	109.5
C3—C2—C1	118.8 (4)	C11—C13—H13A	109.5
C3—C2—C11	120.7 (4)	C11—C13—H13B	109.5
C1—C2—C11	120.4 (5)	H13A—C13—H13B	109.5
C2—C3—C4	123.5 (5)	C11—C13—H13C	109.5
C2—C3—H3A	118.3	H13A—C13—H13C	109.5
C4—C3—H3A	118.3	H13B—C13—H13C	109.5
C5—C4—C3	118.4 (5)	C11—C14—H14A	109.5
C5—C4—H4A	120.8	C11—C14—H14B	109.5
C3—C4—H4A	120.8	H14A—C14—H14B	109.5
C4—C5—C6	121.2 (5)	C11—C14—H14C	109.5
C4—C5—H5A	119.4	H14A—C14—H14C	109.5
C6—C5—H5A	119.4	H14B—C14—H14C	109.5
C5—C6—C1	121.1 (4)	O2—C15—C17	120.6 (6)
C5—C6—C7	115.2 (4)	O2—C15—C16	122.2 (6)
C1—C6—C7	123.7 (5)	C17—C15—C16	117.2 (6)
N1—C7—C6	127.0 (4)	C15—C16—H16A	109.8
N1—C7—H7A	116.5	C15—C16—H16B	109.1
C6—C7—H7A	116.5	H16A—C16—H16B	110.0
C9—C8—C8i	119.4 (3)	C15—C17—H17A	109.4
C9—C8—N1	124.8 (5)	C15—C17—H17B	110.0
C8i—C8—N1	115.8 (3)	H17A—C17—H17B	109.4
O1i—Zn1—O1—C1	157.2 (3)	C4—C5—C6—C1	2.1 (7)
N1—Zn1—O1—C1	−8.1 (4)	C4—C5—C6—C7	−176.2 (4)
N1i—Zn1—O1—C1	40.3 (8)	O1—C1—C6—C5	179.0 (4)
O2—Zn1—O1—C1	−99.2 (4)	C2—C1—C6—C5	−1.3 (6)
O1i—Zn1—O2—C15	50.10 (11)	O1—C1—C6—C7	−2.9 (7)
O1—Zn1—O2—C15	−50.10 (11)	C2—C1—C6—C7	176.8 (4)
N1—Zn1—O2—C15	−140.55 (12)	C8—N1—C7—C6	−176.1 (4)
N1i—Zn1—O2—C15	140.55 (12)	Zn1—N1—C7—C6	5.7 (6)
O1i—Zn1—N1—C7	−117.8 (6)	C5—C6—C7—N1	172.7 (4)
O1—Zn1—N1—C7	0.1 (4)	C1—C6—C7—N1	−5.5 (7)
N1i—Zn1—N1—C7	−167.4 (3)	C7—N1—C8—C9	−10.0 (6)
O2—Zn1—N1—C7	101.8 (4)	Zn1—N1—C8—C9	168.4 (3)
O1i—Zn1—N1—C8	63.9 (6)	C7—N1—C8—C8i	169.4 (3)
O1—Zn1—N1—C8	−178.2 (3)	Zn1—N1—C8—C8i	−12.2 (3)
N1i—Zn1—N1—C8	14.3 (3)	C8i—C8—C9—C10	−1.1 (5)
O2—Zn1—N1—C8	−76.6 (3)	N1—C8—C9—C10	178.3 (4)
Zn1—O1—C1—C6	10.3 (6)	C8—C9—C10—C10i	1.1 (5)
Zn1—O1—C1—C2	−169.4 (3)	C3—C2—C11—C13	−117.0 (6)
O1—C1—C2—C3	179.1 (4)	C1—C2—C11—C13	62.5 (6)
C6—C1—C2—C3	−0.6 (6)	C3—C2—C11—C12	2.0 (6)
O1—C1—C2—C11	−0.4 (6)	C1—C2—C11—C12	−178.6 (4)
C6—C1—C2—C11	179.9 (4)	C3—C2—C11—C14	121.3 (5)
C1—C2—C3—C4	1.9 (7)	C1—C2—C11—C14	−59.2 (6)
C11—C2—C3—C4	−178.6 (4)	Zn1—O2—C15—C17	180.0
C2—C3—C4—C5	−1.1 (8)	Zn1—O2—C15—C16	0.000 (1)
C3—C4—C5—C6	−0.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O1	0.96	2.37	3.022 (7)	124
C14—H14C···O1	0.96	2.41	2.983 (6)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O1	0.96	2.37	3.022 (7)	124
C14—H14C⋯O1	0.96	2.41	2.983 (6)	118