Diaqua­bis­(1-methyl-1H-imidazole-κN3)bis­[2-(naphthalen-1-yl)acetato-κO]cobalt(II)

Zhao, H.; Yin, F.-J.; Xu, X.-Y.; Han, L.-J.

doi:10.1107/S1600536812013505

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m533

doi:10.1107/S1600536812013505

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Diaquabis(1-methyl-1H-imidazole-κN³)bis[2-(naphthalen-1-yl)acetato-κO]cobalt(II)

Hong Zhao,^a Fu-Jun Yin,^b ^* Xing-You Xu ^c and Li-Jun Han ^d

^aDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bJiangsu Marine Resources Development Research Institute, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^cHuaiyin Insititute of Technology, Huaiyin 223003, People's Republic of China, and ^dDepartment of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China
^*Correspondence e-mail: yfj1999@126.com

(Received 3 March 2012; accepted 28 March 2012; online 4 April 2012)

In the title compound, [Co(C₁₂H₉O₂)₂(C₄H₆N₂)₂(H₂O)₂], the Co^II ion is located on an inversion centre and displays a distorted octahedral coordination geometry. Two O atoms from two water molecules and two carboxylate O atoms from two 2-(naphthalen-1-yl)acetate ligands are in the equatorial plane and two N atoms from two 1-methyl-1H-imidazole ligands are in the axial positions. The structure is stabilized by intramolecular O—H⋯O hydrogen bonds. Intermolecular O—H⋯O hydrogen bonds link the complex molecules into chains along [100].

Related literature

For the structures of related complexes with 2-(naphthalen-1-yl)acetate ligands, see: Duan et al. (2007 ); Ji et al. (2011 ); Tang et al. (2006 ); Yang et al. (2008 ); Yin et al. (2011 ).

Experimental

Crystal data

[Co(C₁₂H₉O₂)₂(C₄H₆N₂)₂(H₂O)₂]
M_r = 629.56
Monoclinic, P 2₁ /c
a = 7.3384 (7) Å
b = 24.582 (2) Å
c = 8.8559 (8) Å
β = 111.158 (1)°
V = 1489.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 298 K
0.34 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.815, T_max = 0.885
13335 measured reflections
3356 independent reflections
2865 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.084
S = 1.05
3356 reflections
203 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.84 (2)	2.13 (2)	2.8523 (18)	144 (2)
O3—H3B⋯O2	0.85 (2)	1.81 (2)	2.6463 (16)	168 (2)
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013505/hy2522sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013505/hy2522Isup2.hkl

checkCIF report

Comment top

In recent years 2-(naphthalen-1-yl)acetate ligand has attracted many interests in coordination chemistry due to its ability to form metal complexes (Duan et al., 2007; Ji et al., 2011; Tang et al., 2006; Yang et al., 2008; Yin et al., 2011). The crystal structure of the title compound was determined as part of an ongoing study of the properties of cobalt complexes containing imidazole ligands.

In the title compound (Fig. 1), the Co^II ion is located on an inversion centre and displays a distorted octahedral coordination geometry. Two O atoms from two water molecules and two carboxylate O atoms from two 2-(naphthalen-1-yl)acetate ligands are in the equatorial plane and two N atoms from two N-methylimidazole ligands are in the axial positions. The structure is stabilized by intramolecular O—H···O hydrogen bonds (Table 1). In the crystal, intermolecular O—H···O hydrogen bonds link the complex molecules into chains along [100] (Fig. 2).

Related literature top

For the structures of related complexes with 2-(naphthalen-1-yl)acetate ligands, see: Duan et al. (2007); Ji et al. (2011); Tang et al. (2006); Yang et al. (2008); Yin et al. (2011).

Experimental top

The title compound was synthesized by the reaction of CoCl₂.6H₂O (71.3 mg, 0.3 mmol), 2-(naphthalen-1-yl)acetic acid (93 mg, 0.5 mmol), N-methylimidazole (32.8 mg, 0.4 mmol) and NaOH (20 mg, 0.5 mmol) in 15 ml of a water-ethanol mixture (v/v 1:1) under solvothermal conditions. The starting mixture was homogenized and transferred into a sealed Teflon-lined bomb (25 ml) and heated at 140° C for three days. After cooling, red crystals of the title compound were obtained, which were washed with distilled water and absolute ethyl alcohol (yield: 26.8% based on Co).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x+1, -y+1, -z.]
	Fig. 2. Part of the chain structure of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds are omitted for clarity.

Diaquabis(1-methyl-1H-imidazole-κN³)bis[2-(naphthalen- 1-yl)acetato-κO]cobalt(II) top

Crystal data top

[Co(C₁₂H₉O₂)₂(C₄H₆N₂)₂(H₂O)₂]	F(000) = 658
M_r = 629.56	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3356 reflections
a = 7.3384 (7) Å	θ = 2.6–27.3°
b = 24.582 (2) Å	µ = 0.63 mm⁻¹
c = 8.8559 (8) Å	T = 298 K
β = 111.158 (1)°	Block, red
V = 1489.8 (2) Å³	0.34 × 0.30 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	2865 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 27.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.815, T_max = 0.885	k = −31→30
13335 measured reflections	l = −11→11

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0408P)² + 0.3567P] where P = (F_o² + 2F_c²)/3
3356 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Co(C₁₂H₉O₂)₂(C₄H₆N₂)₂(H₂O)₂]	V = 1489.8 (2) Å³
M_r = 629.56	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3384 (7) Å	µ = 0.63 mm⁻¹
b = 24.582 (2) Å	T = 298 K
c = 8.8559 (8) Å	0.34 × 0.30 × 0.20 mm
β = 111.158 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3356 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2865 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.885	R_int = 0.024
13335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	2 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.25 e Å⁻³
3356 reflections	Δρ_min = −0.28 e Å⁻³
203 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
Co1	0.5000	0.5000	0.0000	0.03250 (10)
N1	0.3651 (2)	0.49725 (5)	−0.25228 (16)	0.0396 (3)
N2	0.2163 (2)	0.46891 (6)	−0.50250 (16)	0.0439 (3)
O1	0.37360 (16)	0.57809 (4)	0.00491 (14)	0.0417 (3)
O2	0.14963 (16)	0.55623 (4)	0.11124 (14)	0.0429 (3)
O3	0.26123 (16)	0.46019 (5)	0.04077 (14)	0.0414 (3)
C1	0.2365 (2)	0.58909 (6)	0.05248 (17)	0.0344 (3)
C2	0.1641 (3)	0.64816 (7)	0.0303 (2)	0.0430 (4)
H2A	0.2760	0.6720	0.0518	0.052*
H2B	0.0803	0.6533	−0.0819	0.052*
C3	0.0536 (2)	0.66527 (6)	0.1363 (2)	0.0405 (4)
C4	−0.1444 (3)	0.67227 (7)	0.0715 (2)	0.0508 (4)
H4	−0.2105	0.6649	−0.0377	0.061*
C5	−0.2506 (3)	0.69042 (8)	0.1662 (3)	0.0631 (6)
H5	−0.3851	0.6951	0.1186	0.076*
C6	−0.1594 (3)	0.70103 (8)	0.3253 (3)	0.0601 (5)
H6	−0.2311	0.7136	0.3859	0.072*
C7	0.0448 (3)	0.69323 (6)	0.4006 (2)	0.0471 (4)
C8	0.1530 (2)	0.67521 (6)	0.3049 (2)	0.0393 (3)
C9	0.3577 (3)	0.66855 (7)	0.3824 (2)	0.0494 (4)
H9	0.4314	0.6567	0.3227	0.059*
C10	0.4479 (3)	0.67927 (9)	0.5436 (3)	0.0636 (5)
H10	0.5826	0.6751	0.5918	0.076*
C11	0.3404 (4)	0.69649 (8)	0.6373 (3)	0.0686 (6)
H11	0.4038	0.7034	0.7471	0.082*
C12	0.1447 (4)	0.70302 (7)	0.5682 (3)	0.0611 (5)
H12	0.0744	0.7141	0.6317	0.073*
C13	0.3534 (3)	0.53921 (7)	−0.3573 (2)	0.0473 (4)
H13	0.4010	0.5742	−0.3270	0.057*
C14	0.2625 (3)	0.52220 (8)	−0.5115 (2)	0.0510 (4)
H14	0.2367	0.5428	−0.6051	0.061*
C15	0.2803 (2)	0.45573 (7)	−0.34511 (19)	0.0428 (4)
H15	0.2666	0.4214	−0.3062	0.051*
C16	0.1186 (3)	0.43256 (10)	−0.6383 (2)	0.0617 (5)
H16A	0.2063	0.4239	−0.6932	0.093*
H16B	0.0045	0.4502	−0.7122	0.093*
H16C	0.0810	0.3997	−0.5986	0.093*
H3A	0.161 (3)	0.4468 (11)	−0.029 (2)	0.093*
H3B	0.222 (4)	0.4886 (7)	0.074 (3)	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.03202 (16)	0.03393 (16)	0.03224 (16)	0.00035 (11)	0.01242 (11)	−0.00172 (11)
N1	0.0412 (7)	0.0412 (7)	0.0347 (7)	0.0010 (6)	0.0119 (6)	0.0007 (6)
N2	0.0419 (7)	0.0557 (9)	0.0331 (7)	−0.0014 (6)	0.0124 (6)	−0.0032 (6)
O1	0.0423 (6)	0.0395 (6)	0.0479 (6)	0.0053 (5)	0.0220 (5)	0.0010 (5)
O2	0.0454 (6)	0.0376 (6)	0.0503 (7)	0.0003 (5)	0.0230 (5)	−0.0017 (5)
O3	0.0391 (6)	0.0393 (6)	0.0479 (7)	−0.0033 (5)	0.0183 (5)	−0.0046 (5)
C1	0.0346 (7)	0.0365 (8)	0.0287 (7)	−0.0001 (6)	0.0074 (6)	−0.0041 (6)
C2	0.0501 (9)	0.0376 (8)	0.0443 (9)	0.0055 (7)	0.0205 (7)	0.0026 (7)
C3	0.0441 (9)	0.0276 (7)	0.0532 (10)	0.0021 (6)	0.0218 (8)	0.0009 (6)
C4	0.0440 (9)	0.0412 (9)	0.0632 (12)	0.0005 (7)	0.0145 (8)	−0.0032 (8)
C5	0.0397 (10)	0.0559 (12)	0.0970 (17)	0.0036 (8)	0.0287 (11)	−0.0024 (11)
C6	0.0599 (12)	0.0485 (11)	0.0881 (16)	0.0029 (9)	0.0462 (12)	−0.0084 (10)
C7	0.0602 (11)	0.0293 (8)	0.0619 (11)	−0.0016 (7)	0.0343 (9)	−0.0039 (7)
C8	0.0457 (9)	0.0255 (7)	0.0511 (9)	−0.0002 (6)	0.0226 (7)	−0.0007 (6)
C9	0.0478 (10)	0.0444 (9)	0.0567 (11)	0.0011 (7)	0.0197 (8)	−0.0005 (8)
C10	0.0605 (12)	0.0554 (12)	0.0640 (13)	−0.0008 (9)	0.0094 (10)	0.0010 (10)
C11	0.0946 (17)	0.0521 (12)	0.0520 (12)	−0.0037 (11)	0.0180 (11)	−0.0053 (9)
C12	0.0958 (17)	0.0387 (10)	0.0614 (13)	−0.0015 (10)	0.0437 (12)	−0.0070 (9)
C13	0.0540 (10)	0.0429 (9)	0.0455 (10)	−0.0023 (8)	0.0186 (8)	0.0039 (7)
C14	0.0554 (11)	0.0575 (11)	0.0402 (9)	0.0035 (9)	0.0173 (8)	0.0105 (8)
C15	0.0467 (9)	0.0444 (9)	0.0364 (8)	−0.0006 (7)	0.0141 (7)	0.0014 (7)
C16	0.0622 (12)	0.0798 (14)	0.0396 (10)	−0.0100 (10)	0.0142 (9)	−0.0162 (9)

Geometric parameters (Å, º) top

Co1—N1	2.0928 (13)	C5—H5	0.9300
Co1—O1	2.1392 (11)	C6—C7	1.416 (3)
Co1—O3	2.1483 (11)	C6—H6	0.9300
N1—C15	1.317 (2)	C7—C12	1.419 (3)
N1—C13	1.371 (2)	C7—C8	1.425 (2)
N2—C15	1.340 (2)	C8—C9	1.418 (2)
N2—C14	1.363 (2)	C9—C10	1.364 (3)
N2—C16	1.461 (2)	C9—H9	0.9300
O1—C1	1.2528 (18)	C10—C11	1.401 (3)
O2—C1	1.2525 (18)	C10—H10	0.9300
O3—H3A	0.84 (2)	C11—C12	1.352 (3)
O3—H3B	0.85 (2)	C11—H11	0.9300
C1—C2	1.534 (2)	C12—H12	0.9300
C2—C3	1.505 (2)	C13—C14	1.352 (3)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—H14	0.9300
C3—C4	1.367 (2)	C15—H15	0.9300
C3—C8	1.427 (2)	C16—H16A	0.9600
C4—C5	1.408 (3)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.349 (3)

N1—Co1—N1ⁱ	180.000 (1)	C6—C5—C4	120.71 (18)
N1—Co1—O1	90.52 (5)	C6—C5—H5	119.6
N1ⁱ—Co1—O1	89.48 (5)	C4—C5—H5	119.6
N1—Co1—O1ⁱ	89.48 (5)	C5—C6—C7	120.51 (18)
N1ⁱ—Co1—O1ⁱ	90.52 (5)	C5—C6—H6	119.7
O1—Co1—O1ⁱ	180.0	C7—C6—H6	119.7
N1—Co1—O3ⁱ	86.31 (5)	C6—C7—C12	121.94 (18)
N1ⁱ—Co1—O3ⁱ	93.69 (5)	C6—C7—C8	118.93 (17)
O1—Co1—O3ⁱ	88.89 (4)	C12—C7—C8	119.13 (17)
O1ⁱ—Co1—O3ⁱ	91.11 (4)	C9—C8—C7	117.92 (16)
N1—Co1—O3	93.69 (5)	C9—C8—C3	122.62 (15)
N1ⁱ—Co1—O3	86.31 (5)	C7—C8—C3	119.46 (15)
O1—Co1—O3	91.11 (4)	C10—C9—C8	120.91 (18)
O1ⁱ—Co1—O3	88.89 (4)	C10—C9—H9	119.5
O3ⁱ—Co1—O3	180.00 (6)	C8—C9—H9	119.5
C15—N1—C13	105.06 (14)	C9—C10—C11	120.9 (2)
C15—N1—Co1	128.77 (11)	C9—C10—H10	119.6
C13—N1—Co1	126.13 (11)	C11—C10—H10	119.6
C15—N2—C14	106.99 (14)	C12—C11—C10	120.1 (2)
C15—N2—C16	126.28 (16)	C12—C11—H11	119.9
C14—N2—C16	126.72 (15)	C10—C11—H11	119.9
C1—O1—Co1	127.40 (10)	C11—C12—C7	121.06 (19)
Co1—O3—H3A	127.2 (18)	C11—C12—H12	119.5
Co1—O3—H3B	94.9 (19)	C7—C12—H12	119.5
H3A—O3—H3B	105 (3)	C14—C13—N1	109.88 (16)
O2—C1—O1	126.26 (14)	C14—C13—H13	125.1
O2—C1—C2	117.33 (13)	N1—C13—H13	125.1
O1—C1—C2	116.37 (14)	C13—C14—N2	106.28 (15)
C3—C2—C1	115.10 (13)	C13—C14—H14	126.9
C3—C2—H2A	108.5	N2—C14—H14	126.9
C1—C2—H2A	108.5	N1—C15—N2	111.79 (15)
C3—C2—H2B	108.5	N1—C15—H15	124.1
C1—C2—H2B	108.5	N2—C15—H15	124.1
H2A—C2—H2B	107.5	N2—C16—H16A	109.5
C4—C3—C8	118.82 (16)	N2—C16—H16B	109.5
C4—C3—C2	120.25 (16)	H16A—C16—H16B	109.5
C8—C3—C2	120.92 (14)	N2—C16—H16C	109.5
C3—C4—C5	121.53 (19)	H16A—C16—H16C	109.5
C3—C4—H4	119.2	H16B—C16—H16C	109.5
C5—C4—H4	119.2

O1—Co1—N1—C15	−139.37 (14)	C6—C7—C8—C9	178.98 (16)
O1ⁱ—Co1—N1—C15	40.63 (14)	C12—C7—C8—C9	−0.8 (2)
O3ⁱ—Co1—N1—C15	131.77 (15)	C6—C7—C8—C3	−0.2 (2)
O3—Co1—N1—C15	−48.23 (15)	C12—C7—C8—C3	179.99 (15)
O1—Co1—N1—C13	43.28 (14)	C4—C3—C8—C9	179.47 (16)
O1ⁱ—Co1—N1—C13	−136.72 (14)	C2—C3—C8—C9	−1.4 (2)
O3ⁱ—Co1—N1—C13	−45.58 (14)	C4—C3—C8—C7	−1.3 (2)
O3—Co1—N1—C13	134.42 (14)	C2—C3—C8—C7	177.79 (14)
N1—Co1—O1—C1	107.01 (13)	C7—C8—C9—C10	−0.2 (3)
N1ⁱ—Co1—O1—C1	−72.99 (13)	C3—C8—C9—C10	178.98 (17)
O3ⁱ—Co1—O1—C1	−166.69 (12)	C8—C9—C10—C11	0.8 (3)
O3—Co1—O1—C1	13.31 (12)	C9—C10—C11—C12	−0.4 (3)
Co1—O1—C1—O2	2.2 (2)	C10—C11—C12—C7	−0.7 (3)
Co1—O1—C1—C2	−175.43 (10)	C6—C7—C12—C11	−178.52 (19)
O2—C1—C2—C3	22.5 (2)	C8—C7—C12—C11	1.2 (3)
O1—C1—C2—C3	−159.65 (14)	C15—N1—C13—C14	−0.2 (2)
C1—C2—C3—C4	−106.75 (18)	Co1—N1—C13—C14	177.66 (12)
C1—C2—C3—C8	74.13 (19)	N1—C13—C14—N2	0.2 (2)
C8—C3—C4—C5	1.8 (3)	C15—N2—C14—C13	−0.06 (19)
C2—C3—C4—C5	−177.34 (16)	C16—N2—C14—C13	−179.08 (17)
C3—C4—C5—C6	−0.6 (3)	C13—N1—C15—N2	0.16 (19)
C4—C5—C6—C7	−1.1 (3)	Co1—N1—C15—N2	−177.62 (10)
C5—C6—C7—C12	−178.80 (19)	C14—N2—C15—N1	−0.07 (19)
C5—C6—C7—C8	1.5 (3)	C16—N2—C15—N1	178.96 (16)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱⁱ	0.84 (2)	2.13 (2)	2.8523 (18)	144 (2)
O3—H3B···O2	0.85 (2)	1.81 (2)	2.6463 (16)	168 (2)

Symmetry code: (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Co(C₁₂H₉O₂)₂(C₄H₆N₂)₂(H₂O)₂]
M_r	629.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.3384 (7), 24.582 (2), 8.8559 (8)
β (°)	111.158 (1)
V (Å³)	1489.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.34 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.815, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	13335, 3356, 2865
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.646

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.05
No. of reflections	3356
No. of parameters	203
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.84 (2)	2.13 (2)	2.8523 (18)	144 (2)
O3—H3B···O2	0.85 (2)	1.81 (2)	2.6463 (16)	168 (2)

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

The authors thank Jiangsu Marine Resources Development Research Institute and Huaihai Institute of Technology for support of this work.

References

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