(2,2′-Bipyridine)(2-formyl-6-methoxy­phenolato)nickel(II) perchlorate

Wang, C.-J.; Ren, P.-D.; Wu, W.-P.; Zhang, Z.-B.

doi:10.1107/S1600536808040385

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m11

doi:10.1107/S1600536808040385

Open

access

(2,2′-Bipyridine)(2-formyl-6-methoxyphenolato)nickel(II) perchlorate

Cui-Juan Wang,^a ^* Ping-Di Ren,^a Wei-Ping Wu ^b and Zhi-Bin Zhang ^a

^aDepartment of Chemistry and Chemical Engineering, School of Bioengineering, Southwest JiaoTong University, Chengdu, Sichuan 610031, People's Republic of China, and ^bDepartment of Chemistry, College of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong, Sichuan 643000, People's Republic of China
^*Correspondence e-mail: wcjsc2000@126.com

(Received 27 November 2008; accepted 1 December 2008; online 6 December 2008)

In the title compound, [Ni(C₈H₇O₃)(C₁₀H₈N₂)]ClO₄, the Ni^II atom is in a slightly distorted square-planar coordination by two N atoms from the 2,2′-bipyridine (bipy) ligand and two O atoms from the deprotonated 2-formyl-6-methoxyphenolate (mbd) ligand. The bipy ligand is nearly coplanar with the Ni^II square plane, the Ni atom being only 0.042 (2) Å from the mean plane, whereas the benzaldehyde plane is folded with respect to the square plane, making a dihedral angle of 19.17 (8)°. One of the O atoms of the perchlorate anion is involved in a weak interaction with the Ni atom, with an Ni—O distance of 2.5732 (18) Å. The packing is stabilized by weak C—H⋯O interactions.

Related literature

For general background, see: Alizadeh et al. (1999 ); Hamblin et al. (2002 ); Minuti et al. (1999 ). For a related structure, see: Liu et al. (2008 ).

Experimental

Crystal data

[Ni(C₈H₇O₃)(C₁₀H₈N₂)]ClO₄
M_r = 465.48
Triclinic, $[P \overline 1]$
a = 8.460 (1) Å
b = 9.580 (1) Å
c = 11.956 (2) Å
α = 84.45 (1)°
β = 80.05 (1)°
γ = 80.25 (1)°
V = 938.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.22 mm⁻¹
T = 298 (2) K
0.32 × 0.26 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.696, T_max = 0.801
3644 measured reflections
3381 independent reflections
2838 reflections with I > 2σ(I)
R_int = 0.009

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.077
S = 1.04
3381 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O7ⁱ	0.93	2.58	3.461 (4)	159
C12—H12⋯O5ⁱⁱ	0.93	2.57	3.499 (3)	177
C15—H15⋯O5ⁱⁱ	0.93	2.59	3.517 (3)	171
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040385/dn2410sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040385/dn2410Isup2.hkl

checkCIF report

Comment top

2,2'-Bipyridyl ligand is bidentate chelating ligand, which can commonly act as terminal ligands, and may also provide molecular interaction sites for molecular recognition or assembly (Minuti et al., 1999; Hamblin et al., 2002). On the other hand, aldehyde ligands have significant importance in chemistry, specially in the development of its complexes, because this type ligands are potentially capable of forming stable complexes with metal ions (Alizadeh et al., 1999). Herein we report the synthesis and characterization of the title complex with mixed co-ligand.

The Ni^II atom in the title complex, has a square coordination formed by two N atoms from Bipy ligand and two O atoms from protonated mbd ligand (Fig. 1). One of the O atom of the perchlorate anion is in weak interaction with the Ni atom with a Ni—O distance of 2.5732 (18) Å. The average Ni—N bond length of 1.98 Å is close to the values observed in related complexes (Liu et al., 2008). The occurrence of C—H···O hydrogen bonding stabilizes the packing (Table 1).

Related literature top

For general background, see: Alizadeh et al. (1999); Hamblin et al. (2002); Minuti et al. (1999). For a related structure, see: Liu et al. (2008).

Experimental top

Bipy (0.023 g, 0.12 mmol), Ni(ClO₄)₂ (0.028 g, 0.13 mmol) and Hmbd (0.020 g, 0.16 mmol), were added in a solvent of ethanol, the mixture was stirring were required. The resultant solution was kept at room temperature for three weeks yielding green crystals of (I)

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular view of compound (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

(2,2'-Bipyridine)(2-formyl-6-methoxyphenolato)nickel(II) perchlorate top

Crystal data top

[Ni(C₈H₇O₃)(C₁₀H₈N₂)]ClO₄	Z = 2
M_r = 465.48	F(000) = 476
Triclinic, P1	D_x = 1.647 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.460 (1) Å	Cell parameters from 3381 reflections
b = 9.580 (1) Å	θ = 1.7–25.2°
c = 11.956 (2) Å	µ = 1.22 mm⁻¹
α = 84.45 (1)°	T = 298 K
β = 80.05 (1)°	Block, green
γ = 80.25 (1)°	0.32 × 0.26 × 0.19 mm
V = 938.4 (2) Å³

Data collection top

Bruker APEXII area-detector diffractometer	3381 independent reflections
Radiation source: fine-focus sealed tube	2838 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.009
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = 0→10
T_min = 0.696, T_max = 0.801	k = −11→11
3644 measured reflections	l = −14→14

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.049P)²] where P = (F_o² + 2F_c²)/3
3381 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Ni(C₈H₇O₃)(C₁₀H₈N₂)]ClO₄	γ = 80.25 (1)°
M_r = 465.48	V = 938.4 (2) Å³
Triclinic, P1	Z = 2
a = 8.460 (1) Å	Mo Kα radiation
b = 9.580 (1) Å	µ = 1.22 mm⁻¹
c = 11.956 (2) Å	T = 298 K
α = 84.45 (1)°	0.32 × 0.26 × 0.19 mm
β = 80.05 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	3381 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2838 reflections with I > 2σ(I)
T_min = 0.696, T_max = 0.801	R_int = 0.009
3644 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
3381 reflections	Δρ_min = −0.50 e Å⁻³
263 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 > 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
Ni1	0.62596 (3)	0.46273 (3)	0.37323 (2)	0.03207 (11)
O1	0.8230 (2)	0.46228 (19)	0.43851 (14)	0.0491 (4)
O2	0.54224 (18)	0.33979 (16)	0.49436 (13)	0.0397 (4)
O3	0.4083 (2)	0.12543 (17)	0.59302 (15)	0.0531 (5)
N1	0.4407 (2)	0.45896 (19)	0.29274 (15)	0.0356 (4)
N2	0.6801 (2)	0.6028 (2)	0.24547 (15)	0.0384 (4)
C1	0.8713 (3)	0.3669 (3)	0.5099 (2)	0.0539 (7)
H1	0.9750	0.3677	0.5258	0.065*
C2	0.7895 (3)	0.2585 (3)	0.5693 (2)	0.0490 (6)
C3	0.8710 (4)	0.1578 (3)	0.6437 (3)	0.0797 (10)
H3	0.9760	0.1654	0.6530	0.096*
C4	0.7985 (5)	0.0514 (3)	0.7010 (3)	0.0935 (13)
H4	0.8532	−0.0131	0.7499	0.112*
C5	0.6424 (4)	0.0376 (3)	0.6871 (2)	0.0711 (9)
H5	0.5940	−0.0367	0.7267	0.085*
C6	0.5578 (3)	0.1319 (2)	0.6157 (2)	0.0462 (6)
C7	0.6294 (3)	0.2479 (2)	0.55657 (18)	0.0390 (5)
C8	0.3359 (4)	0.0033 (3)	0.6415 (2)	0.0662 (8)
H8A	0.4119	−0.0814	0.6251	0.099*
H8B	0.2399	0.0015	0.6094	0.099*
H8C	0.3075	0.0084	0.7225	0.099*
C9	0.3265 (3)	0.3750 (3)	0.3212 (2)	0.0416 (5)
H9	0.3278	0.3148	0.3870	0.050*
C10	0.2074 (3)	0.3751 (3)	0.2563 (2)	0.0503 (6)
H10	0.1300	0.3151	0.2774	0.060*
C11	0.2044 (3)	0.4647 (3)	0.1599 (2)	0.0544 (7)
H11	0.1239	0.4668	0.1154	0.065*
C12	0.3211 (3)	0.5518 (3)	0.1291 (2)	0.0512 (6)
H12	0.3208	0.6129	0.0637	0.061*
C13	0.4388 (3)	0.5464 (2)	0.19728 (18)	0.0380 (5)
C14	0.5734 (3)	0.6303 (2)	0.17170 (18)	0.0393 (5)
C15	0.5939 (4)	0.7291 (3)	0.0798 (2)	0.0557 (7)
H15	0.5181	0.7493	0.0304	0.067*
C16	0.7279 (4)	0.7967 (3)	0.0627 (2)	0.0634 (8)
H16	0.7435	0.8629	0.0011	0.076*
C17	0.8374 (4)	0.7669 (3)	0.1357 (2)	0.0594 (7)
H17	0.9291	0.8113	0.1244	0.071*
C18	0.8102 (3)	0.6699 (3)	0.2267 (2)	0.0484 (6)
H18	0.8848	0.6500	0.2770	0.058*
Cl	0.82646 (7)	0.24175 (6)	0.14548 (5)	0.04118 (15)
O4	0.8132 (2)	0.2621 (2)	0.26486 (14)	0.0597 (5)
O5	0.6696 (2)	0.2285 (2)	0.12270 (17)	0.0753 (6)
O6	0.8814 (3)	0.3620 (2)	0.07874 (16)	0.0652 (5)
O7	0.9370 (3)	0.1160 (2)	0.11921 (17)	0.0757 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03248 (17)	0.03601 (17)	0.03033 (16)	−0.01101 (12)	−0.01119 (11)	0.00581 (11)
O1	0.0452 (10)	0.0571 (11)	0.0506 (10)	−0.0154 (8)	−0.0172 (8)	−0.0019 (9)
O2	0.0396 (9)	0.0392 (9)	0.0400 (9)	−0.0051 (7)	−0.0130 (7)	0.0092 (7)
O3	0.0633 (12)	0.0395 (10)	0.0524 (10)	−0.0135 (9)	0.0016 (9)	0.0073 (8)
N1	0.0376 (10)	0.0365 (10)	0.0333 (9)	−0.0057 (8)	−0.0090 (8)	0.0003 (8)
N2	0.0423 (11)	0.0382 (11)	0.0351 (10)	−0.0104 (9)	−0.0028 (8)	−0.0029 (8)
C1	0.0450 (15)	0.0599 (17)	0.0627 (17)	−0.0026 (13)	−0.0254 (13)	−0.0138 (14)
C2	0.0554 (16)	0.0417 (14)	0.0545 (15)	0.0006 (12)	−0.0293 (13)	−0.0036 (12)
C3	0.087 (2)	0.059 (2)	0.104 (3)	0.0030 (18)	−0.065 (2)	0.0011 (19)
C4	0.133 (3)	0.053 (2)	0.109 (3)	−0.004 (2)	−0.084 (3)	0.0223 (19)
C5	0.116 (3)	0.0403 (16)	0.0610 (18)	−0.0093 (17)	−0.0372 (18)	0.0122 (13)
C6	0.0663 (17)	0.0351 (13)	0.0367 (12)	−0.0047 (12)	−0.0126 (12)	0.0014 (10)
C7	0.0525 (14)	0.0325 (12)	0.0317 (11)	0.0029 (11)	−0.0144 (10)	−0.0039 (9)
C8	0.090 (2)	0.0397 (15)	0.0617 (18)	−0.0221 (15)	0.0168 (16)	0.0003 (13)
C9	0.0405 (13)	0.0436 (14)	0.0427 (13)	−0.0110 (11)	−0.0101 (10)	0.0012 (11)
C10	0.0427 (14)	0.0594 (17)	0.0530 (15)	−0.0150 (13)	−0.0107 (12)	−0.0059 (13)
C11	0.0469 (15)	0.0707 (19)	0.0503 (15)	−0.0073 (14)	−0.0226 (12)	−0.0046 (14)
C12	0.0531 (15)	0.0616 (17)	0.0414 (14)	−0.0082 (13)	−0.0201 (12)	0.0045 (12)
C13	0.0421 (13)	0.0389 (12)	0.0320 (11)	−0.0016 (10)	−0.0085 (10)	−0.0009 (10)
C14	0.0454 (14)	0.0381 (13)	0.0330 (11)	−0.0040 (11)	−0.0050 (10)	−0.0019 (10)
C15	0.0692 (18)	0.0561 (17)	0.0394 (14)	−0.0127 (14)	−0.0074 (13)	0.0109 (12)
C16	0.082 (2)	0.0588 (18)	0.0454 (15)	−0.0230 (16)	0.0032 (15)	0.0125 (13)
C17	0.0655 (19)	0.0593 (18)	0.0523 (16)	−0.0256 (15)	0.0086 (14)	−0.0028 (14)
C18	0.0479 (14)	0.0509 (15)	0.0484 (14)	−0.0199 (12)	−0.0002 (11)	−0.0046 (12)
Cl	0.0437 (3)	0.0428 (3)	0.0378 (3)	−0.0086 (3)	−0.0106 (2)	0.0041 (2)
O4	0.0798 (13)	0.0620 (12)	0.0386 (9)	−0.0123 (10)	−0.0148 (9)	0.0014 (9)
O5	0.0592 (12)	0.1022 (17)	0.0741 (14)	−0.0325 (12)	−0.0310 (10)	0.0178 (12)
O6	0.0829 (14)	0.0616 (12)	0.0546 (11)	−0.0305 (11)	−0.0136 (10)	0.0177 (9)
O7	0.0816 (15)	0.0588 (13)	0.0725 (14)	0.0163 (11)	0.0001 (11)	−0.0044 (11)

Geometric parameters (Å, º) top

Ni1—O2	1.8932 (15)	C8—H8B	0.9600
Ni1—O1	1.9580 (16)	C8—H8C	0.9600
Ni1—N2	1.9783 (19)	C9—C10	1.374 (3)
Ni1—N1	1.9828 (18)	C9—H9	0.9300
O1—C1	1.255 (3)	C10—C11	1.370 (3)
O2—C7	1.310 (3)	C10—H10	0.9300
O3—C6	1.351 (3)	C11—C12	1.379 (4)
O3—C8	1.439 (3)	C11—H11	0.9300
N1—C9	1.339 (3)	C12—C13	1.384 (3)
N1—C13	1.349 (3)	C12—H12	0.9300
N2—C18	1.343 (3)	C13—C14	1.476 (3)
N2—C14	1.346 (3)	C14—C15	1.386 (3)
C1—C2	1.412 (4)	C15—C16	1.374 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C7	1.410 (3)	C16—C17	1.359 (4)
C2—C3	1.421 (4)	C16—H16	0.9300
C3—C4	1.348 (5)	C17—C18	1.374 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.388 (5)	C18—H18	0.9300
C4—H4	0.9300	Cl—O7	1.4194 (19)
C5—C6	1.378 (4)	Cl—O5	1.4284 (19)
C5—H5	0.9300	Cl—O6	1.4336 (18)
C6—C7	1.425 (3)	Cl—O4	1.4418 (17)
C8—H8A	0.9600

O2—Ni1—O1	92.24 (7)	O3—C8—H8C	109.5
O2—Ni1—N2	171.66 (7)	H8A—C8—H8C	109.5
O1—Ni1—N2	94.93 (7)	H8B—C8—H8C	109.5
O2—Ni1—N1	91.43 (7)	N1—C9—C10	122.1 (2)
O1—Ni1—N1	174.35 (7)	N1—C9—H9	119.0
N2—Ni1—N1	81.75 (8)	C10—C9—H9	119.0
C1—O1—Ni1	122.66 (17)	C11—C10—C9	119.0 (2)
C7—O2—Ni1	125.39 (15)	C11—C10—H10	120.5
C6—O3—C8	116.8 (2)	C9—C10—H10	120.5
C9—N1—C13	119.0 (2)	C10—C11—C12	119.7 (2)
C9—N1—Ni1	126.47 (15)	C10—C11—H11	120.1
C13—N1—Ni1	114.47 (15)	C12—C11—H11	120.1
C18—N2—C14	118.7 (2)	C11—C12—C13	118.7 (2)
C18—N2—Ni1	126.43 (17)	C11—C12—H12	120.7
C14—N2—Ni1	114.84 (15)	C13—C12—H12	120.7
O1—C1—C2	128.7 (2)	N1—C13—C12	121.5 (2)
O1—C1—H1	115.7	N1—C13—C14	114.52 (19)
C2—C1—H1	115.7	C12—C13—C14	124.0 (2)
C7—C2—C1	121.7 (2)	N2—C14—C15	121.0 (2)
C7—C2—C3	119.4 (3)	N2—C14—C13	114.38 (19)
C1—C2—C3	119.0 (3)	C15—C14—C13	124.6 (2)
C4—C3—C2	121.0 (3)	C16—C15—C14	119.1 (3)
C4—C3—H3	119.5	C16—C15—H15	120.4
C2—C3—H3	119.5	C14—C15—H15	120.4
C3—C4—C5	120.2 (3)	C17—C16—C15	119.9 (3)
C3—C4—H4	119.9	C17—C16—H16	120.0
C5—C4—H4	119.9	C15—C16—H16	120.0
C6—C5—C4	121.3 (3)	C16—C17—C18	118.8 (3)
C6—C5—H5	119.4	C16—C17—H17	120.6
C4—C5—H5	119.4	C18—C17—H17	120.6
O3—C6—C5	126.1 (3)	N2—C18—C17	122.4 (3)
O3—C6—C7	114.1 (2)	N2—C18—H18	118.8
C5—C6—C7	119.8 (3)	C17—C18—H18	118.8
O2—C7—C2	123.6 (2)	O7—Cl—O5	109.87 (14)
O2—C7—C6	118.2 (2)	O7—Cl—O6	110.45 (13)
C2—C7—C6	118.3 (2)	O5—Cl—O6	109.20 (12)
O3—C8—H8A	109.5	O7—Cl—O4	109.12 (12)
O3—C8—H8B	109.5	O5—Cl—O4	108.41 (12)
H8A—C8—H8B	109.5	O6—Cl—O4	109.75 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O7ⁱ	0.93	2.58	3.461 (4)	159
C12—H12···O5ⁱⁱ	0.93	2.57	3.499 (3)	177
C15—H15···O5ⁱⁱ	0.93	2.59	3.517 (3)	171

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₇O₃)(C₁₀H₈N₂)]ClO₄
M_r	465.48
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.460 (1), 9.580 (1), 11.956 (2)
α, β, γ (°)	84.45 (1), 80.05 (1), 80.25 (1)
V (Å³)	938.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.22
Crystal size (mm)	0.32 × 0.26 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.696, 0.801
No. of measured, independent and observed [I > 2σ(I)] reflections	3644, 3381, 2838
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.077, 1.04
No. of reflections	3381
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.50

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O7ⁱ	0.93	2.58	3.461 (4)	159.1
C12—H12···O5ⁱⁱ	0.93	2.57	3.499 (3)	176.9
C15—H15···O5ⁱⁱ	0.93	2.59	3.517 (3)	171.2

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z.

Acknowledgements

The authors are grateful to the Young Teacher Underway Science Foundation of Southwest JiaoTong University for financial support.

References

Alizadeh, N., Ershad, S., Naeimi, H., Sharghi, H. & Shamsipur, M. (1999). Pol. J. Chem. 73, 915–925. CAS Google Scholar
Bruker (2004). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hamblin, J., Childs, L. J., Alcock, N. W. & Hannon, M. J. (2002). J. Chem. Soc. Dalton Trans. pp. 164–169. Web of Science CSD CrossRef Google Scholar
Liu, W. L., Ye, L. F., Liu, X. F., Yuan, L. M., Jiang, J. X. & Yan, C. G. (2008). CrystEngComm, 10, 1395–1403. Web of Science CSD CrossRef CAS Google Scholar
Minuti, L., Taticchi, A., Marrocchi, A., Gacs-Baitz, E. & Galeazzi, R. (1999). Eur. J. Org. Chem. pp. 3155–3163. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar