Bis[2-(4-benzo­yloxy-2-hy­droxy­benzo­yl)-1-phenyl­ethenolato]diethano­lzinc(II)

Dong, K.; Sun, J.; Ruan, B.-F.; Gong, H.-B.

doi:10.1107/S1600536810036202

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1290

doi:10.1107/S1600536810036202

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Bis[2-(4-benzoyloxy-2-hydroxybenzoyl)-1-phenylethenolato]diethanolzinc(II)

Kai Dong,^a Juan Sun,^a Ban-Feng Ruan ^a ^* and Hai-Bin Gong ^a,^b ^*

^aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China, and ^bXuzhou Central Hospital, Xuzhou Cardiovascular Disease Institute, Xuzhou 221009, Jiangsu, People's Republic of China
^*Correspondence e-mail: bf_ruan@163.com, adler_20008@yahoo.com.cn

(Received 2 September 2010; accepted 8 September 2010; online 25 September 2010)

The mononuclear title complex, [Zn(C₂₂H₁₅O₅)₂(C₂H₅OH)₂], contains a Zn^II atom (site symmetry $[\overline{1}]$ ) surrounded by six O atoms of the keto groups of two substituted 1,3-diketonate ligands and of two ethanol molecules, resulting in a distorted octahedral coordination environment. The molecular configuration is stabilized by an intramolecular hydrogen bond between the phenolic hydroxy group and the adjacent keto group. The hydroxy group acts likewise as an acceptor of an intermolecular O—H⋯O hydrogen bond with the hydroxy group of the ethanol molecule as the donor. The hydrogen-bonding scheme leads to the formation of supramolecular layers parallel to (010).

Related literature

For the role of zinc in enzymes and in bioinorganic chemistry, see: Bertini et al. (1994 ); Lipscomb & Strater (1996 ); Vallee & Auld (1993 ); Zhu et al. (2003 ).

Experimental

Crystal data

[Zn(C₂₂H₁₅O₅)₂(C₂H₆O)₂]
M_r = 876.19
Triclinic, $[P \overline 1]$
a = 7.170 (5) Å
b = 9.399 (5) Å
c = 16.457 (5) Å
α = 106.590 (5)°
β = 95.596 (5)°
γ = 90.989 (5)°
V = 1056.6 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.830, T_max = 0.882
6185 measured reflections
4255 independent reflections
2898 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.142
S = 1.02
4255 reflections
279 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O5ⁱ	2.002 (2)
Zn1—O4ⁱ	2.034 (2)
Zn1—O6ⁱ	2.203 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.82	1.74	2.470 (3)	147
O6—H10A⋯O3ⁱⁱ	0.86	2.04	2.824 (4)	151
Symmetry code: (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036202/wm2402sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036202/wm2402Isup2.hkl

checkCIF report

Comment top

Zinc, the second most abundant transition metal in biology, functions as the active site of hydrolytic enzymes, such as carboxypeptidase and carbonic anhydrase, where it is in a hard donor coordination environment of nitrogen and oxygen (Lipscomb & Strater, 1996; Bertini et al., 1994). Zinc has long been recognized as an important cofactor in biological molecules, either as a structural template in protein folding or as a Lewis acid catalyst that can readily adopt 4-, 5- or 6-coordination (Vallee & Auld, 1993). Studies of the structures and properties of the metal coordination sites in in zinc enzymes recently were in focus in the field of bioinorganic chemistry (Zhu et al., 2003). A couple of chemical systems have been developed to reproduce the zinc coordination core. On our continuation of the research in this field, the crystal structure of a mononuclear zinc(II) compound, (I), is reported here.

In the structure of (I), the Zn^II atom is situated on an inversion center and adopts a slightly distorted octahedral coordination (Fig. 1). It is surrounded by six O atoms from the keto groups of two 1,3-diketonate ligands and by two ethanol molecules. The Zn^II atom and the four O atoms from the diketone ligands form the equatorial plane with similar Zn—O bond lengths of 2.002 (2) and 2.034 (2) Å. The two ethanol O atoms are in the axial positions with considerably longer Zn—O bond lengths of 2.203 (3) Å (Table 1). The two trans-angles at the zinc(II) center are 180° by symmetry; all angles around Zn1 are close to 90°, ranging from 85.93 (11) to 94.07 (11)°. In the crystal structure, intramolecular and intermolecular O—H···O hydrogen bonding leads to a layered assembly parallel to (010) (Table 2; Fig. 2).

Related literature top

For the role of zinc in enzymes and in bioinorganic chemistry, see: Bertini et al. (1994); Lipscomb & Strater (1996); Vallee & Auld (1993); Zhu et al. (2003).

Experimental top

To a ethanol solution (15 ml) of 3-hydroxy-4-(3-oxo-3-phenylpropanoyl)phenyl benzoic acid (0.36 g, 0.001mol), anhydrous zinc acetate (0.092 g, 0.0005 mol) was added at room temperature. After addition, the reaction mixture was refluxed for 30 min with stirring and then was filtered. Single crystals of the title compound were obtained by slow evaporation of the filtrate.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure and atom-numbering scheme of the title compound (I), showing 30% probability displacement ellipsoids. [Symmetry code: (A) -x, -y+1, -z+1.]
	Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen bonding interactions are indicated by dashed lines.

Bis[2-(4-benzoyloxy-2-hydroxybenzoyl)-1-phenylethenolato]diethanolzinc(II) top

Crystal data top

[Zn(C₂₂H₁₅O₅)₂(C₂H₆O)₂]	Z = 1
M_r = 876.19	F(000) = 456
Triclinic, P1	D_x = 1.377 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.170 (5) Å	Cell parameters from 2800 reflections
b = 9.399 (5) Å	θ = 2.5–26.2°
c = 16.457 (5) Å	µ = 0.65 mm⁻¹
α = 106.590 (5)°	T = 298 K
β = 95.596 (5)°	Block, colourless
γ = 90.989 (5)°	0.30 × 0.20 × 0.20 mm
V = 1056.6 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4255 independent reflections
Radiation source: fine-focus sealed tube	2898 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→8
T_min = 0.830, T_max = 0.882	k = −11→11
6185 measured reflections	l = −18→20

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0597P)² + 0.7172P] where P = (F_o² + 2F_c²)/3
4255 reflections	(Δ/σ)_max < 0.001
279 parameters	Δρ_max = 0.80 e Å⁻³
14 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Zn(C₂₂H₁₅O₅)₂(C₂H₆O)₂]	γ = 90.989 (5)°
M_r = 876.19	V = 1056.6 (10) Å³
Triclinic, P1	Z = 1
a = 7.170 (5) Å	Mo Kα radiation
b = 9.399 (5) Å	µ = 0.65 mm⁻¹
c = 16.457 (5) Å	T = 298 K
α = 106.590 (5)°	0.30 × 0.20 × 0.20 mm
β = 95.596 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4255 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2898 reflections with I > 2σ(I)
T_min = 0.830, T_max = 0.882	R_int = 0.017
6185 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	14 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	Δρ_max = 0.80 e Å⁻³
4255 reflections	Δρ_min = −0.49 e Å⁻³
279 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	1.0307 (7)	0.0321 (6)	−0.1364 (3)	0.0787 (14)
H1	1.1025	−0.0287	−0.1751	0.094*
C2	1.0779 (7)	0.1805 (6)	−0.1042 (3)	0.0828 (14)
H2	1.1814	0.2205	−0.1214	0.099*
C3	0.9730 (6)	0.2707 (5)	−0.0466 (3)	0.0670 (11)
H3A	1.0040	0.3720	−0.0260	0.080*
C4	0.8221 (5)	0.2120 (4)	−0.0193 (2)	0.0465 (8)
C5	0.7732 (5)	0.0614 (4)	−0.0524 (2)	0.0572 (10)
H5	0.6708	0.0209	−0.0347	0.069*
C6	0.8769 (7)	−0.0277 (5)	−0.1115 (3)	0.0723 (12)
H6	0.8431	−0.1283	−0.1345	0.087*
C7	0.7210 (5)	0.3140 (5)	0.0470 (2)	0.0522 (9)
C8	0.4913 (5)	0.3187 (4)	0.1426 (2)	0.0533 (9)
C9	0.3464 (5)	0.4014 (5)	0.1234 (2)	0.0625 (11)
H9	0.3287	0.4179	0.0701	0.075*
C10	0.2282 (5)	0.4591 (4)	0.1841 (2)	0.0560 (10)
H10	0.1290	0.5137	0.1707	0.067*
C11	0.2513 (4)	0.4390 (4)	0.2655 (2)	0.0417 (8)
C12	0.4069 (5)	0.3582 (4)	0.2832 (2)	0.0462 (8)
C13	0.5241 (5)	0.2980 (4)	0.2214 (2)	0.0539 (9)
H13	0.6247	0.2436	0.2336	0.065*
C14	0.1192 (4)	0.4955 (4)	0.3303 (2)	0.0427 (8)
C15	−0.0393 (5)	0.5691 (4)	0.3129 (2)	0.0475 (8)
H15	−0.0592	0.5804	0.2584	0.057*
C16	−0.1725 (4)	0.6280 (4)	0.3689 (2)	0.0409 (7)
C17	−0.3308 (4)	0.7128 (4)	0.3413 (2)	0.0425 (8)
C18	−0.3685 (5)	0.7198 (5)	0.2587 (2)	0.0648 (11)
H18	−0.2969	0.6672	0.2169	0.078*
C19	−0.5106 (6)	0.8032 (6)	0.2374 (3)	0.0817 (14)
H19	−0.5329	0.8071	0.1815	0.098*
C20	−0.6184 (6)	0.8797 (6)	0.2966 (3)	0.0816 (14)
H20	−0.7108	0.9394	0.2824	0.098*
C21	−0.5890 (7)	0.8675 (6)	0.3773 (3)	0.0971 (18)
H21	−0.6660	0.9158	0.4179	0.117*
C22	−0.4472 (6)	0.7849 (5)	0.3996 (3)	0.0749 (13)
H22	−0.4299	0.7778	0.4551	0.090*
C23	0.1763 (9)	0.8386 (7)	0.5795 (5)	0.132 (2)
H23A	0.1946	0.8477	0.5236	0.159*
H23B	0.2850	0.8879	0.6176	0.159*
C24	0.0214 (9)	0.9216 (7)	0.6062 (5)	0.129 (2)
H24A	−0.0890	0.8780	0.5689	0.193*
H24B	0.0426	1.0218	0.6046	0.193*
H24C	0.0044	0.9217	0.6634	0.193*
O1	0.7452 (5)	0.4469 (3)	0.0716 (2)	0.0838 (10)
O2	0.5993 (4)	0.2389 (3)	0.07885 (17)	0.0653 (7)
O3	0.4461 (4)	0.3341 (4)	0.36033 (16)	0.0670 (8)
H3	0.3672	0.3722	0.3917	0.100*
O4	0.1634 (3)	0.4709 (3)	0.40277 (15)	0.0600 (7)
O5	−0.1712 (3)	0.6190 (3)	0.44437 (14)	0.0547 (7)
O6	0.1818 (4)	0.6942 (3)	0.5742 (2)	0.0773 (9)
H10A	0.2735	0.6729	0.6057	0.093*
Zn1	0.0000	0.5000	0.5000	0.0548 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.084 (3)	0.097 (4)	0.057 (3)	0.036 (3)	0.033 (2)	0.014 (3)
C2	0.083 (3)	0.093 (4)	0.089 (3)	0.017 (3)	0.055 (3)	0.035 (3)
C3	0.068 (3)	0.065 (3)	0.077 (3)	0.008 (2)	0.033 (2)	0.026 (2)
C4	0.0436 (19)	0.058 (2)	0.0402 (18)	0.0108 (17)	0.0117 (15)	0.0155 (17)
C5	0.051 (2)	0.063 (3)	0.057 (2)	0.0030 (19)	0.0140 (18)	0.0138 (19)
C6	0.078 (3)	0.066 (3)	0.063 (3)	0.013 (2)	0.014 (2)	0.002 (2)
C7	0.045 (2)	0.061 (3)	0.053 (2)	0.0063 (18)	0.0159 (16)	0.0166 (19)
C8	0.049 (2)	0.057 (2)	0.055 (2)	0.0120 (18)	0.0262 (17)	0.0105 (18)
C9	0.061 (2)	0.087 (3)	0.049 (2)	0.019 (2)	0.0232 (18)	0.027 (2)
C10	0.049 (2)	0.076 (3)	0.052 (2)	0.0238 (19)	0.0175 (16)	0.0276 (19)
C11	0.0332 (17)	0.050 (2)	0.0443 (18)	0.0100 (14)	0.0108 (13)	0.0142 (15)
C12	0.0352 (17)	0.059 (2)	0.0461 (19)	0.0112 (16)	0.0106 (14)	0.0148 (17)
C13	0.0413 (19)	0.062 (2)	0.060 (2)	0.0182 (17)	0.0158 (16)	0.0157 (19)
C14	0.0331 (17)	0.056 (2)	0.0419 (18)	0.0105 (15)	0.0102 (13)	0.0158 (16)
C15	0.0419 (19)	0.066 (2)	0.0399 (18)	0.0205 (17)	0.0128 (14)	0.0207 (17)
C16	0.0343 (17)	0.051 (2)	0.0398 (18)	0.0085 (15)	0.0068 (13)	0.0150 (15)
C17	0.0362 (17)	0.050 (2)	0.0434 (18)	0.0107 (15)	0.0061 (14)	0.0152 (15)
C18	0.058 (2)	0.096 (3)	0.053 (2)	0.033 (2)	0.0175 (18)	0.037 (2)
C19	0.075 (3)	0.121 (4)	0.066 (3)	0.046 (3)	0.010 (2)	0.050 (3)
C20	0.068 (3)	0.105 (4)	0.082 (3)	0.049 (3)	0.008 (2)	0.041 (3)
C21	0.088 (3)	0.139 (5)	0.073 (3)	0.078 (3)	0.027 (3)	0.034 (3)
C22	0.072 (3)	0.111 (4)	0.051 (2)	0.054 (3)	0.019 (2)	0.030 (2)
C23	0.112 (4)	0.086 (2)	0.197 (5)	0.020 (3)	−0.007 (4)	0.044 (3)
C24	0.114 (4)	0.110 (4)	0.147 (4)	0.040 (3)	0.014 (3)	0.009 (3)
O1	0.092 (2)	0.0581 (19)	0.098 (2)	0.0027 (17)	0.0523 (19)	0.0045 (17)
O2	0.0656 (17)	0.0624 (17)	0.0721 (18)	0.0123 (14)	0.0423 (14)	0.0140 (14)
O3	0.0497 (15)	0.107 (2)	0.0525 (15)	0.0400 (15)	0.0158 (12)	0.0316 (16)
O4	0.0456 (14)	0.100 (2)	0.0461 (14)	0.0360 (14)	0.0165 (11)	0.0350 (14)
O5	0.0496 (14)	0.0804 (18)	0.0429 (13)	0.0331 (13)	0.0165 (11)	0.0264 (13)
O6	0.0566 (17)	0.0793 (18)	0.092 (2)	0.0247 (15)	−0.0049 (15)	0.0215 (17)
Zn1	0.0475 (4)	0.0847 (5)	0.0425 (3)	0.0331 (3)	0.0159 (3)	0.0296 (3)

Geometric parameters (Å, º) top

C1—C2	1.366 (7)	C15—H15	0.9300
C1—C6	1.378 (6)	C16—O5	1.269 (4)
C1—H1	0.9300	C16—C17	1.506 (4)
C2—C3	1.373 (6)	C17—C22	1.372 (5)
C2—H2	0.9300	C17—C18	1.379 (5)
C3—C4	1.375 (5)	C18—C19	1.375 (5)
C3—H3A	0.9300	C18—H18	0.9300
C4—C5	1.389 (5)	C19—C20	1.352 (6)
C4—C7	1.489 (5)	C19—H19	0.9300
C5—C6	1.377 (5)	C20—C21	1.363 (6)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.374 (5)
C7—O1	1.202 (4)	C21—H21	0.9300
C7—O2	1.346 (4)	C22—H22	0.9300
C8—C13	1.365 (5)	C23—O6	1.337 (6)
C8—C9	1.374 (5)	C23—C24	1.402 (6)
C8—O2	1.411 (4)	C23—H23A	0.9700
C9—C10	1.372 (5)	C23—H23B	0.9700
C9—H9	0.9300	C24—H24A	0.9600
C10—C11	1.400 (5)	C24—H24B	0.9600
C10—H10	0.9300	C24—H24C	0.9600
C11—C12	1.414 (4)	O3—H3	0.8200
C11—C14	1.486 (4)	O4—Zn1	2.034 (2)
C12—O3	1.356 (4)	O5—Zn1	2.002 (2)
C12—C13	1.383 (5)	O6—Zn1	2.203 (3)
C13—H13	0.9300	O6—H10A	0.8600
C14—O4	1.289 (4)	Zn1—O5ⁱ	2.002 (2)
C14—C15	1.389 (4)	Zn1—O4ⁱ	2.034 (2)
C15—C16	1.402 (4)	Zn1—O6ⁱ	2.203 (3)

C2—C1—C6	120.2 (4)	C18—C17—C16	123.2 (3)
C2—C1—H1	119.9	C19—C18—C17	120.9 (4)
C6—C1—H1	119.9	C19—C18—H18	119.5
C1—C2—C3	120.2 (4)	C17—C18—H18	119.5
C1—C2—H2	119.9	C20—C19—C18	121.0 (4)
C3—C2—H2	119.9	C20—C19—H19	119.5
C2—C3—C4	120.4 (4)	C18—C19—H19	119.5
C2—C3—H3A	119.8	C19—C20—C21	118.7 (4)
C4—C3—H3A	119.8	C19—C20—H20	120.7
C3—C4—C5	119.4 (3)	C21—C20—H20	120.7
C3—C4—C7	117.8 (3)	C20—C21—C22	121.0 (4)
C5—C4—C7	122.8 (3)	C20—C21—H21	119.5
C6—C5—C4	119.8 (4)	C22—C21—H21	119.5
C6—C5—H5	120.1	C17—C22—C21	120.9 (4)
C4—C5—H5	120.1	C17—C22—H22	119.6
C5—C6—C1	119.9 (4)	C21—C22—H22	119.6
C5—C6—H6	120.0	O6—C23—C24	121.8 (6)
C1—C6—H6	120.0	O6—C23—H23A	106.9
O1—C7—O2	122.9 (3)	C24—C23—H23A	106.9
O1—C7—C4	125.4 (3)	O6—C23—H23B	106.9
O2—C7—C4	111.7 (3)	C24—C23—H23B	106.9
C13—C8—C9	121.4 (3)	H23A—C23—H23B	106.7
C13—C8—O2	117.3 (3)	C23—C24—H24A	109.5
C9—C8—O2	121.0 (3)	C23—C24—H24B	109.5
C10—C9—C8	118.9 (3)	H24A—C24—H24B	109.5
C10—C9—H9	120.6	C23—C24—H24C	109.5
C8—C9—H9	120.6	H24A—C24—H24C	109.5
C9—C10—C11	122.5 (3)	H24B—C24—H24C	109.5
C9—C10—H10	118.7	C7—O2—C8	119.2 (3)
C11—C10—H10	118.7	C12—O3—H3	109.5
C10—C11—C12	116.4 (3)	C14—O4—Zn1	126.7 (2)
C10—C11—C14	122.9 (3)	C16—O5—Zn1	126.6 (2)
C12—C11—C14	120.7 (3)	C23—O6—Zn1	132.2 (4)
O3—C12—C13	117.2 (3)	C23—O6—H10A	114.0
O3—C12—C11	121.8 (3)	Zn1—O6—H10A	113.8
C13—C12—C11	121.0 (3)	O5—Zn1—O5ⁱ	180.00 (11)
C8—C13—C12	119.7 (3)	O5—Zn1—O4	89.37 (9)
C8—C13—H13	120.1	O5ⁱ—Zn1—O4	90.63 (9)
C12—C13—H13	120.1	O5—Zn1—O4ⁱ	90.63 (9)
O4—C14—C15	123.3 (3)	O5ⁱ—Zn1—O4ⁱ	89.37 (9)
O4—C14—C11	115.0 (3)	O4—Zn1—O4ⁱ	179.999 (1)
C15—C14—C11	121.7 (3)	O5—Zn1—O6	94.07 (11)
C14—C15—C16	126.8 (3)	O5ⁱ—Zn1—O6	85.93 (11)
C14—C15—H15	116.6	O4—Zn1—O6	89.52 (12)
C16—C15—H15	116.6	O4ⁱ—Zn1—O6	90.48 (12)
O5—C16—C15	125.3 (3)	O5—Zn1—O6ⁱ	85.93 (11)
O5—C16—C17	114.8 (3)	O5ⁱ—Zn1—O6ⁱ	94.07 (11)
C15—C16—C17	119.9 (3)	O4—Zn1—O6ⁱ	90.48 (12)
C22—C17—C18	117.4 (3)	O4ⁱ—Zn1—O6ⁱ	89.52 (12)
C22—C17—C16	119.4 (3)	O6—Zn1—O6ⁱ	180.0

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.74	2.470 (3)	147
O6—H10A···O3ⁱⁱ	0.86	2.04	2.824 (4)	151

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₂₂H₁₅O₅)₂(C₂H₆O)₂]
M_r	876.19
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.170 (5), 9.399 (5), 16.457 (5)
α, β, γ (°)	106.590 (5), 95.596 (5), 90.989 (5)
V (Å³)	1056.6 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.830, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	6185, 4255, 2898
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.142, 1.02
No. of reflections	4255
No. of parameters	279
No. of restraints	14
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.49

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O5ⁱ	2.002 (2)	Zn1—O6ⁱ	2.203 (3)
Zn1—O4ⁱ	2.034 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.74	2.470 (3)	147.1
O6—H10A···O3ⁱⁱ	0.86	2.04	2.824 (4)	151.2

Symmetry code: (ii) −x+1, −y+1, −z+1.

Acknowledgements

The work was financed by a grant (project 30772627) from the National Natural Science Foundation of China.

References

Bertini, I., Gray, H. B., Lippard, S. J. & Valentine, J. S. (1994). Bioinorganic Chemistry. Mills Valley, CA, USA: University Science Books. Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lipscomb, W. N. & Strater, N. (1996). Chem. Rev. 96, 2375–2434. CrossRef PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vallee, B. L. & Auld, D. S. (1993). Acc. Chem. Res. 26, 543–551. CrossRef CAS Web of Science Google Scholar
Zhu, H.-L., Meng, F.-J., Wang, Z.-D. & Yang, F. (2003). Z. Kristallogr. New Cryst. Struct. 219, 321–322. Google Scholar

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Volume 66| Part 10| October 2010| Page m1290

doi:10.1107/S1600536810036202

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[2-(4-benzo­yl­oxy-2-hy­dr­oxy­benzo­yl)-1-phenyl­ethenolato]di­ethano­lzinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[2-(4-benzoyloxy-2-hydroxybenzoyl)-1-phenylethenolato]diethanolzinc(II)