Bis(2-{[(9H-fluoren-2-yl)methyl­idene]amino}­phenolato-κ2N,O)zinc methanol disolvate

Kim, Y.-I.; Yun, S.-J.; Hwang, I.-H.; Kim, D.-Y.; Kang, S.K.

doi:10.1107/S160053681201272X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages m504-m505

doi:10.1107/S160053681201272X

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Bis(2-{[(9H-fluoren-2-yl)methylidene]amino}phenolato-κ²N,O)zinc methanol disolvate

Young-Inn Kim,^a Sung-Jae Yun,^a Inn-Hye Hwang,^a Dae-Young Kim ^a and Sung Kwon Kang ^b ^*

^aDepartment of Chemistry Education and Interdisciplinary Program of Advanced Information and Display Materials, Pusan National University, Busan 609-735, Republic of Korea, and ^bDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

(Received 20 March 2012; accepted 23 March 2012; online 31 March 2012)

In the title compound, [Zn(C₂₀H₁₄NO)₂]·2CH₃OH, the Zn^II atom lies on a crystallographic twofold rotation axis and is coordinated by two O atoms and two N atoms from two bidentate 2-{[(9H-fluoren-2-yl)methylidene]amino}phenolate ligands within a distorted tetrahedral geometry. The dihedral angle between the two chelate rings is 82.92 (5)°. In the coordinated ligand, the phenol ring is twisted at 30.22 (9)° from the mean plane of the fluorene ring. In the crystal, O—H⋯O hydrogen bonds link the complex molecules to the methanol solvent molecules.

Related literature

For general background to Schiff base complexes, see: Ji et al. (2012 ); Niu et al. (2012 ); Liu et al. (2011 ); Roy et al. (2009 ). For the structures and luminescent properties of Hg(II) complexes, see: Kim et al. (2011 ); Kim & Kang (2010 ). For the physical properties of fluorene complexes, see: Scaria et al. (2010 ); Loy et al. (2002 ); Miteva et al. (2001 ).

Experimental

Crystal data

[Zn(C₂₀H₁₄NO)₂]·2CH₄O
M_r = 698.1
Monoclinic, C 2/c
a = 13.7294 (3) Å
b = 13.9123 (2) Å
c = 18.8383 (3) Å
β = 110.652 (1)°
V = 3367.03 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.78 mm⁻¹
T = 296 K
0.10 × 0.05 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.922, T_max = 0.966
10682 measured reflections
3078 independent reflections
2134 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.096
S = 1.02
3078 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.9239 (17)
Zn1—N8	2.052 (2)
C7—N8	1.433 (3)
N8—C9	1.293 (3)

O1ⁱ—Zn1—O1	115.61 (11)
O1ⁱ—Zn1—N8	125.99 (8)
O1—Zn1—N8	85.68 (8)
N8—Zn1—N8ⁱ	122.53 (11)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O24—H24⋯O1	0.98 (4)	1.82 (5)	2.794 (3)	173 (4)

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201272X/tk5073sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201272X/tk5073Isup2.hkl

checkCIF report

Comment top

Schiff base ligands have attracted attention due to their facile syntheses, easily tunable steric and electronic properties resulting in a good performance in sensor technologies and electroluminescence devices (Ji et al., 2012; Niu et al., 2012; Liu et al., 2011; Roy et al., 2009). Recently, we reported group 12, Hg(II) complexes with Schiff bases with an emphasis on their luminescent properties (Kim & Kang, 2010; Kim et al., 2011). Herein, we designed new Schiff base containing a fluorene moiety since flourene has high triplet energy and good-hole transporting ability (Scaria et al., 2010; Loy et al., 2002; Miteva et al., 2001) and synthesized its Zn(II) complex. The title compound shows a red emission at 611 nm with a quantum yield of 1.2% in a DMF solution upon 300 nm excitation.

In (I), Fig. 1, the Zn^II atom lies on a twofold axis and is coordinated by two O atoms and two N atoms of two bidentate 2-((9H-fluoren-2-yl)methyleneamino)phenolato ligands in a distorted tetrahedral geometry. The angles around Zn atom are within the range of 85.68 (8)–125.99 (8) ° (Table 1). The dihedral angle between the O1/Zn1/N8 and O1ⁱ/Zn1/N1ⁱ [symmetry code: (i) -x + 1, y, -z + 3/2] is 83.48 (6) °. The fluorene moiety (C9—C22) is almost planar, with r.m.s. deviations of 0.018 Å from the corresponding least-squares plane defined by the thirteen constituent atoms. In the 2-((9H-fluoren-2-yl)methyleneamino)phenol ligand, the phenol ring (O1–C7) is twisted at 30.22 (9) ° from the mean plane of the fluorene ring. The presence of intermolecular O24—H24···O1 hydrogen bonds link the complex and solvent molecules (Table 2 and Fig. 1).

Related literature top

For general background to Schiff base complexes, see: Ji et al. (2012); Niu et al. (2012); Liu et al. (2011); Roy et al. (2009). For the structures and luminescent properties of Hg(II) complexes, see: Kim et al. (2011); Kim & Kang (2010). For the physical properties of fluorene complexes, see: Scaria et al. (2010); Loy et al. (2002); Miteva et al. (2001).

Experimental top

Preparation of ligand: 9H-fluorene-2-carbaldehyde (1.94 g, 10 mmol) was slowly added to 2-aminophenol (1.09 g, 10 mmol) in methanol/methylenechloride (1:1 v/v) (40 ml) solution at 50 °C for 5 h to obtain (E)-2-((9H-fluoren-2-yl)methyleneamino)phenol (L) as a yellow powder. Yield: 1.55 g (75%).

Preparation of zinc(II) compound: the reaction of L compound (1.50 g, 10 mmol) with zinc(II) acetate (0.91 g, 5 mmol) in methanol/methylenechloride (1:1 v/v) (40 ml) at 50 °C for 5 h yielded the title compound as an orange powder. The powder was filtered off and washed with hexane. Yield: 0.95 g (30%). Orange crystals of (I) were obtained from its ethanol solution by slow evaporation of the solvent at room temperature.

Structure description top

For general background to Schiff base complexes, see: Ji et al. (2012); Niu et al. (2012); Liu et al. (2011); Roy et al. (2009). For the structures and luminescent properties of Hg(II) complexes, see: Kim et al. (2011); Kim & Kang (2010). For the physical properties of fluorene complexes, see: Scaria et al. (2010); Loy et al. (2002); Miteva et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. The O—H···O hydrogen bonds are indicated by dashed lines. [symmetry code: (i) -x + 1, y, -z + 3/2].

Bis(2-{[(9H-fluoren-2-yl)methylidene]amino}phenolato- κ²N,O)zinc methanol disolvate top

Crystal data top

[Zn(C₂₀H₁₄NO)₂]·2CH₄O	F(000) = 1456
M_r = 698.1	D_x = 1.377 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2869 reflections
a = 13.7294 (3) Å	θ = 2.2–25.3°
b = 13.9123 (2) Å	µ = 0.78 mm⁻¹
c = 18.8383 (3) Å	T = 296 K
β = 110.652 (1)°	Block, orange
V = 3367.03 (10) Å³	0.1 × 0.05 × 0.04 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2134 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→16
T_min = 0.922, T_max = 0.966	k = −13→16
10682 measured reflections	l = −22→16
3078 independent 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0431P)² + 0.3461P] where P = (F_o² + 2F_c²)/3
3078 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Zn(C₂₀H₁₄NO)₂]·2CH₄O	V = 3367.03 (10) Å³
M_r = 698.1	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.7294 (3) Å	µ = 0.78 mm⁻¹
b = 13.9123 (2) Å	T = 296 K
c = 18.8383 (3) Å	0.1 × 0.05 × 0.04 mm
β = 110.652 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3078 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2134 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.966	R_int = 0.039
10682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
3078 reflections	Δρ_min = −0.32 e Å⁻³
227 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.5	0.57842 (3)	0.75	0.04130 (18)
O1	0.40411 (14)	0.65210 (12)	0.66885 (10)	0.0454 (5)
C2	0.3082 (2)	0.61436 (18)	0.64660 (16)	0.0400 (7)
C3	0.2277 (2)	0.6498 (2)	0.58475 (17)	0.0515 (8)
H3	0.2406	0.7007	0.5573	0.062*
C4	0.1294 (3)	0.6119 (2)	0.56296 (17)	0.0558 (8)
H4	0.0765	0.6381	0.5217	0.067*
C5	0.1082 (2)	0.5351 (2)	0.60185 (17)	0.0558 (8)
H5	0.0419	0.5083	0.586	0.067*
C6	0.1861 (2)	0.4984 (2)	0.66416 (16)	0.0499 (8)
H6	0.1721	0.4467	0.6903	0.06*
C7	0.2851 (2)	0.53798 (18)	0.68829 (15)	0.0380 (7)
N8	0.37074 (17)	0.50751 (14)	0.75354 (12)	0.0372 (5)
C9	0.3537 (2)	0.45901 (18)	0.80656 (16)	0.0433 (7)
H9	0.2846	0.4457	0.7997	0.052*
C10	0.4315 (2)	0.42353 (17)	0.87534 (15)	0.0410 (7)
C11	0.3957 (2)	0.38990 (19)	0.93208 (16)	0.0468 (7)
H11	0.3245	0.3882	0.9225	0.056*
C12	0.4632 (2)	0.35952 (18)	1.00140 (16)	0.0456 (7)
H12	0.4382	0.3384	1.0386	0.055*
C13	0.5689 (2)	0.36100 (17)	1.01473 (15)	0.0404 (7)
C14	0.6578 (2)	0.33320 (18)	1.08148 (15)	0.0414 (7)
C15	0.6623 (3)	0.29326 (19)	1.15031 (17)	0.0507 (8)
H15	0.6014	0.2809	1.1597	0.061*
C16	0.7570 (3)	0.2723 (2)	1.20397 (18)	0.0619 (9)
H16	0.7606	0.2456	1.2501	0.074*
C17	0.8467 (3)	0.2908 (2)	1.1897 (2)	0.0730 (10)
H17	0.9106	0.2766	1.2269	0.088*
C18	0.8446 (3)	0.3300 (2)	1.1216 (2)	0.0697 (10)
H18	0.906	0.342	1.1129	0.084*
C19	0.7496 (2)	0.35077 (19)	1.06721 (17)	0.0510 (8)
C20	0.7238 (2)	0.3916 (2)	0.98824 (17)	0.0548 (8)
H20A	0.7525	0.4556	0.9899	0.066*
H20B	0.75	0.3506	0.9574	0.066*
C21	0.6071 (2)	0.39376 (18)	0.95847 (16)	0.0411 (7)
C22	0.5384 (2)	0.42345 (18)	0.88995 (16)	0.0456 (7)
H22	0.5633	0.4439	0.8525	0.055*
C23	0.4138 (3)	0.9024 (3)	0.6538 (2)	0.0906 (12)
H23A	0.3826	0.8908	0.6003	0.136*
H23B	0.4867	0.8876	0.6704	0.136*
H23C	0.4049	0.9688	0.6641	0.136*
O24	0.36624 (18)	0.84464 (18)	0.69240 (13)	0.0716 (7)
H24	0.385 (3)	0.778 (3)	0.687 (2)	0.141 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0383 (3)	0.0397 (3)	0.0464 (3)	0	0.0155 (2)	0
O1	0.0421 (13)	0.0433 (11)	0.0542 (12)	−0.0024 (9)	0.0210 (10)	0.0088 (9)
C2	0.0394 (19)	0.0400 (15)	0.0429 (18)	0.0036 (14)	0.0176 (16)	0.0002 (14)
C3	0.052 (2)	0.0487 (17)	0.053 (2)	0.0051 (16)	0.0180 (18)	0.0143 (15)
C4	0.046 (2)	0.064 (2)	0.0497 (19)	0.0113 (17)	0.0070 (17)	0.0078 (16)
C5	0.044 (2)	0.066 (2)	0.054 (2)	−0.0049 (17)	0.0124 (18)	0.0040 (17)
C6	0.046 (2)	0.0517 (17)	0.0512 (19)	−0.0036 (16)	0.0163 (17)	0.0059 (15)
C7	0.0383 (18)	0.0370 (14)	0.0400 (16)	0.0024 (13)	0.0155 (15)	−0.0011 (13)
N8	0.0392 (14)	0.0354 (12)	0.0392 (13)	0.0002 (11)	0.0165 (12)	0.0007 (11)
C9	0.0421 (19)	0.0404 (15)	0.0502 (19)	−0.0046 (14)	0.0197 (16)	−0.0011 (14)
C10	0.0484 (19)	0.0363 (14)	0.0405 (17)	−0.0011 (14)	0.0184 (15)	0.0020 (14)
C11	0.0410 (19)	0.0538 (17)	0.0475 (19)	−0.0024 (14)	0.0178 (16)	0.0054 (15)
C12	0.047 (2)	0.0503 (17)	0.0452 (18)	0.0003 (15)	0.0232 (16)	0.0069 (14)
C13	0.045 (2)	0.0310 (14)	0.0466 (18)	−0.0013 (14)	0.0177 (16)	−0.0020 (13)
C14	0.046 (2)	0.0336 (15)	0.0435 (17)	0.0020 (13)	0.0141 (16)	0.0006 (13)
C15	0.054 (2)	0.0461 (17)	0.051 (2)	0.0051 (15)	0.0167 (18)	0.0000 (15)
C16	0.070 (3)	0.058 (2)	0.053 (2)	0.0075 (19)	0.015 (2)	0.0081 (16)
C17	0.052 (2)	0.078 (2)	0.070 (2)	0.0054 (19)	−0.002 (2)	0.016 (2)
C18	0.047 (2)	0.078 (2)	0.076 (3)	−0.0037 (18)	0.013 (2)	0.017 (2)
C19	0.046 (2)	0.0468 (17)	0.057 (2)	−0.0035 (15)	0.0131 (18)	0.0079 (15)
C20	0.045 (2)	0.0551 (18)	0.067 (2)	−0.0028 (15)	0.0223 (17)	0.0119 (16)
C21	0.0400 (18)	0.0382 (15)	0.0450 (18)	−0.0013 (13)	0.0151 (16)	0.0045 (13)
C22	0.050 (2)	0.0434 (16)	0.0505 (19)	−0.0010 (15)	0.0262 (17)	0.0063 (15)
C23	0.076 (3)	0.095 (3)	0.102 (3)	−0.004 (2)	0.032 (3)	0.034 (2)
O24	0.0702 (17)	0.0578 (14)	0.0988 (18)	−0.0035 (12)	0.0448 (15)	0.0010 (13)

Geometric parameters (Å, º) top

Zn1—O1ⁱ	1.9239 (18)	C12—H12	0.93
Zn1—O1	1.9239 (17)	C13—C21	1.413 (3)
Zn1—N8	2.052 (2)	C13—C14	1.462 (4)
Zn1—N8ⁱ	2.052 (2)	C14—C15	1.392 (4)
O1—C2	1.341 (3)	C14—C19	1.399 (4)
C2—C3	1.383 (4)	C15—C16	1.367 (4)
C2—C7	1.422 (4)	C15—H15	0.93
C3—C4	1.370 (4)	C16—C17	1.374 (4)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.384 (4)	C17—C18	1.385 (4)
C4—H4	0.93	C17—H17	0.93
C5—C6	1.376 (4)	C18—C19	1.376 (4)
C5—H5	0.93	C18—H18	0.93
C6—C7	1.387 (4)	C19—C20	1.513 (4)
C6—H6	0.93	C20—C21	1.499 (4)
C7—N8	1.433 (3)	C20—H20A	0.97
N8—C9	1.293 (3)	C20—H20B	0.97
C9—C10	1.445 (4)	C21—C22	1.367 (4)
C9—H9	0.93	C22—H22	0.93
C10—C22	1.395 (4)	C23—O24	1.392 (4)
C10—C11	1.404 (3)	C23—H23A	0.96
C11—C12	1.374 (4)	C23—H23B	0.96
C11—H11	0.93	C23—H23C	0.96
C12—C13	1.384 (4)	O24—H24	0.98 (4)

O1ⁱ—Zn1—O1	115.61 (11)	C12—C13—C21	120.8 (3)
O1ⁱ—Zn1—N8	125.99 (8)	C12—C13—C14	131.0 (3)
O1—Zn1—N8	85.68 (8)	C21—C13—C14	108.2 (3)
O1ⁱ—Zn1—N8ⁱ	85.68 (8)	C15—C14—C19	120.1 (3)
O1—Zn1—N8ⁱ	125.99 (8)	C15—C14—C13	131.0 (3)
N8—Zn1—N8ⁱ	122.53 (11)	C19—C14—C13	108.9 (2)
C2—O1—Zn1	111.18 (15)	C16—C15—C14	119.5 (3)
O1—C2—C3	121.9 (3)	C16—C15—H15	120.3
O1—C2—C7	120.4 (3)	C14—C15—H15	120.3
C3—C2—C7	117.7 (3)	C15—C16—C17	120.0 (3)
C4—C3—C2	121.7 (3)	C15—C16—H16	120
C4—C3—H3	119.2	C17—C16—H16	120
C2—C3—H3	119.2	C16—C17—C18	121.8 (3)
C3—C4—C5	120.5 (3)	C16—C17—H17	119.1
C3—C4—H4	119.8	C18—C17—H17	119.1
C5—C4—H4	119.8	C19—C18—C17	118.5 (3)
C6—C5—C4	119.5 (3)	C19—C18—H18	120.7
C6—C5—H5	120.2	C17—C18—H18	120.7
C4—C5—H5	120.2	C18—C19—C14	120.1 (3)
C5—C6—C7	120.6 (3)	C18—C19—C20	130.0 (3)
C5—C6—H6	119.7	C14—C19—C20	109.9 (3)
C7—C6—H6	119.7	C21—C20—C19	102.9 (2)
C6—C7—C2	119.9 (3)	C21—C20—H20A	111.2
C6—C7—N8	125.2 (2)	C19—C20—H20A	111.2
C2—C7—N8	114.8 (2)	C21—C20—H20B	111.2
C9—N8—C7	120.0 (2)	C19—C20—H20B	111.2
C9—N8—Zn1	132.1 (2)	H20A—C20—H20B	109.1
C7—N8—Zn1	106.68 (16)	C22—C21—C13	119.4 (3)
N8—C9—C10	126.4 (3)	C22—C21—C20	130.6 (3)
N8—C9—H9	116.8	C13—C21—C20	110.0 (3)
C10—C9—H9	116.8	C21—C22—C10	121.0 (2)
C22—C10—C11	118.4 (3)	C21—C22—H22	119.5
C22—C10—C9	124.8 (2)	C10—C22—H22	119.5
C11—C10—C9	116.7 (3)	O24—C23—H23A	109.5
C12—C11—C10	121.7 (3)	O24—C23—H23B	109.5
C12—C11—H11	119.1	H23A—C23—H23B	109.5
C10—C11—H11	119.1	O24—C23—H23C	109.5
C11—C12—C13	118.7 (3)	H23A—C23—H23C	109.5
C11—C12—H12	120.6	H23B—C23—H23C	109.5
C13—C12—H12	120.6	C23—O24—H24	108 (2)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···O1	0.98 (4)	1.82 (5)	2.794 (3)	173 (4)

Experimental details

Crystal data
Chemical formula	[Zn(C₂₀H₁₄NO)₂]·2CH₄O
M_r	698.1
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	13.7294 (3), 13.9123 (2), 18.8383 (3)
β (°)	110.652 (1)
V (Å³)	3367.03 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.1 × 0.05 × 0.04

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.922, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	10682, 3078, 2134
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.096, 1.02
No. of reflections	3078
No. of parameters	227
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.32

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Zn1—O1	1.9239 (17)	C7—N8	1.433 (3)
Zn1—N8	2.052 (2)	N8—C9	1.293 (3)

O1ⁱ—Zn1—O1	115.61 (11)	O1—Zn1—N8	85.68 (8)
O1ⁱ—Zn1—N8	125.99 (8)	N8—Zn1—N8ⁱ	122.53 (11)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···O1	0.98 (4)	1.82 (5)	2.794 (3)	173 (4)

Acknowledgements

This work was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 20110003799).

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