(Acetone-κO){6,6′-di-tert-butyl-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4O,N,N′,O′}zinc(II)

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.; Adnan, R.

doi:10.1107/S1600536808011215

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m738-m739

doi:10.1107/S1600536808011215

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(Acetone-κO){6,6′-di-tert-butyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N′,O′}zinc(II)

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Suchada Chantrapromma,^b § Hoong-Kun Fun ^c ^* and Rohana Adnan ^a

^aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 19 April 2008; accepted 20 April 2008; online 30 April 2008)

The molecule of the title compound, [Zn(C₂₈H₃₀N₂O₂)(CH₃COCH₃)], lies across a mirror plane with the Zn^II ion and the acetone molecule on the mirror plane. The Zn^II ion is in a five-coordinate distorted square-pyramidal N₂O₃ environment, with the two imine N and two phenolic O atoms of the tetradentate Schiff base dianion in the basal plane and the acetone molecule 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 molecules are arranged into antiparallel 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_r = 550.11
Monoclinic, C 2/m
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[F² > 2σ(F²)] = 0.073
wR(F²) = 0.190
S = 1.20
2756 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 1.50 e Å⁻³
Δρ_min = −1.15 e Å⁻³

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

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 ).

Supporting information

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

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

checkCIF report

Comment top

Schiff base ligands containing oxygen and imine nitrogen atoms and their metal complexes have gained increased interest in the field of synthetic chemistry due to their variety of applications. Zinc complexes play important roles in various biological systems such as neurotransmission, signal transduction and gene expression (Assaf & Chung, 1984; Berg & Shi, 1996). It is well known that certain zinc complexes with Schiff-bases are biologically active and show very good cytotoxicity against leukemic cells (Tarafder et al., 2002). Previously, we reported the crystal structures of five coordination Zn^II complexes with Schiff base ligands (Eltayeb et al., 2007a;2007b; 2007c. As a continuation of our research on Schiff base complexes, we report here the crystal structure of a Zn^II complex of a closely-related ligand.

The asymmetric unit of the title compound contain one-half of the [Zn(C₂₈H₃₀N₂O₂)(CH₃COCH₃)] complex, with the other half generated by a crystallographic mirror plane. Atoms Zn1, O2, C15, C16, C17, H16A and H17A lie on the mirror plane. The Zn^II ion is five-coordinate and adopts a distorted square-pyramidal geometry, with the two imine N (N1 and N1A) and two phenolic O (O1 and O1A) atoms of the tetradentate Schiff base dianion forming a square base, while the acetone molecule occupies the apical coordination site. The two phenolic O atoms and two imine N atoms are in mutually cis positions. The Zn—O and Zn—N distances in the N₂O₂ coordination plane [1.949 (4) and 2.078 (4) Å, respectively] are in the same ranges as those observed in the other closely related Zn^II complexes of N₂O₂ Schiff base ligands (Eltayeb et al., 2007a; 2007b; 2007c; Reglinski et al. (2002). The apical Zn—O(acetone) distance is 2.182 (4) Å. Other bond lengths and angles observed in the structure are also normal (Allen et al., 1987). The Zn^II ion is displaced from the O1/N1/O1A/N1A plane by 0.023 Å toward the apical acetone molecule. The basal bond angles O–Zn–N [O1–Zn1–N1 = 90.24 (15) °] are close to 90° whereas the O–Zn–O [O1–Zn1–O1A = 97.4 (2)°] angle is bigger than 90° and the N–Mn–N [N1–Zn1–N1A = 78.9 (2)°] angle is smaller than 90°. The bond angles between the O2 atom of the acetone molecule and the atoms in the basal plane are in the range 91.02 (13) to 101.67 (13)°, indicating a distorted square-pyramidal geometry. Coordination of the the N₂O₂ chelate ligand to the Zn^II ion results in the formation of a five-membered ring (Zn1/N1/C8/C8A/N1A) and two six-membered rings viz. Zn1/O1/C1/C6/C7/N1 and Zn1/O1A/C1A/C6A/C7A/N1A. The central benzene ring (C8–C9–C10–C8A–C9A–C10A) makes a dihedral angle of 16.5 (2)° with the outer phenolate rings.

Intramolecular C—H···O weak interactions are observed (Table 1). In the crystal packing (Fig. 2), the molecules are arranged into antiparallel columns along the a axis.

Related literature top

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 top

The title compound was synthesized by adding 3-tert-butyl-2-hydroxybenzaldehyde (0.7 ml, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for half an hour. Zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was refluxed at room temperature for two hours. A yellow-orange precipitate was obtained. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from acetone by slow evaporation of the solvent at room temperature after a few days.

Computing details top

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

Figures top

	Fig. 1. The structure of the title complex, showing 50% probability displacement ellipsoids and the atomic numbering. Atoms labeled with the suffix A are generated by the symmetry operation (x, -y, z). Atoms Zn1, O2, C15, C16 and C17 lie on the crystallographic mirror plane.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the b axis.

(Acetone-κO){6,6'-di-tert-butyl- 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato- κ⁴O,N,N',O'}zinc(II) top

Crystal data top

[Zn(C₂₈H₃₀N₂O₂)(C₃H₆O)]	F(000) = 1160
M_r = 550.11	D_x = 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 = 2.3–26.0°
b = 16.3602 (19) Å	µ = 0.94 mm⁻¹
c = 15.729 (2) Å	T = 100 K
β = 94.446 (10)°	Plate, yellow
V = 2714.4 (6) Å³	0.57 × 0.24 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2756 independent reflections
Radiation source: fine-focus sealed tube	2613 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −20→20
T_min = 0.616, T_max = 0.935	l = −19→19
29567 measured reflections

Refinement top

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0669P)² + 29.8359P] where P = (F_o² + 2F_c²)/3
2756 reflections	(Δ/σ)_max = 0.001
178 parameters	Δρ_max = 1.50 e Å⁻³
0 restraints	Δρ_min = −1.15 e Å⁻³

Crystal data top

[Zn(C₂₈H₃₀N₂O₂)(C₃H₆O)]	V = 2714.4 (6) Å³
M_r = 550.11	Z = 4
Monoclinic, C2/m	Mo Kα radiation
a = 10.5803 (16) Å	µ = 0.94 mm⁻¹
b = 16.3602 (19) Å	T = 100 K
c = 15.729 (2) Å	0.57 × 0.24 × 0.07 mm
β = 94.446 (10)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2756 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2613 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.935	R_int = 0.090
29567 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0669P)² + 29.8359P] where P = (F_o² + 2F_c²)/3
2756 reflections	Δρ_max = 1.50 e Å⁻³
178 parameters	Δρ_min = −1.15 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry code: (i) x, −y, z.

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	[Zn(C₂₈H₃₀N₂O₂)(C₃H₆O)]
M_r	550.11
Crystal system, space group	Monoclinic, C2/m
Temperature (K)	100
a, b, c (Å)	10.5803 (16), 16.3602 (19), 15.729 (2)
β (°)	94.446 (10)
V (Å³)	2714.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.57 × 0.24 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.616, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	29567, 2756, 2613
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.190, 1.20
No. of reflections	2756
No. of parameters	178
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0669P)² + 29.8359P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.50, −1.15

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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

Footnotes

‡On study leave from International University of Africa, Sudan. E-mail: nasertaha90@hotmail.com.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the E-Science Fund and RU research grants (PKIMIA/613308, PKIMIA/815002, 203/PKIMIA/671083) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose Grant No. 1001/PFIZIK/811012.

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