Bis(1H-benzimidazole-κN3)bis­[2-(naphthalen-1-yl)acetato-κ2O,O′]manganese(II) monohydrate

Zhang, Z.-M.; Yin, F.-J.; Li, S.-A.; Wang, L.-P.

doi:10.1107/S1600536812007441

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m328

doi:10.1107/S1600536812007441

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Bis(1H-benzimidazole-κN³)bis[2-(naphthalen-1-yl)acetato-κ²O,O′]manganese(II) monohydrate

Zhen-Ming Zhang,^a,^b ^* Fu-Jun Yin,^c Shu-An Li ^c and Li-Ping Wang ^a

^aCollege of Environment Science and Spatial Infomatics, China University of Mining & Technology, Xuzhou, Jiangsu 221008, People's Republic of China, ^bDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, and ^cJiangsu Marine Resources Development Research Institute, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China
^*Correspondence e-mail: zhangzmlyg@126.com

(Received 10 February 2012; accepted 19 February 2012; online 24 February 2012)

In the title compound, [Mn(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O, the Mn^II ion is located on a twofold rotation axis and six-coordinated, displaying a distorted MnN₂O₄ octahedral geometry. The crystal packing is stabilized by N—H⋯O hydrogen bonds, which give rise to a one-dimensional structure along [001], and π–π interactions between the imidazole rings and between the benzene rings of the 2-(naphthalen-1-yl)acetate ligands [centroid–centroid distances = 3.761 (3) and 3.728 (4) Å]. The contribution of the electron density associated with the disordered water molecules was not considerd in the final structure model.

Related literature

For related structures 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

[Mn(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O
M_r = 679.62
Monoclinic, C 2/c
a = 11.654 (7) Å
b = 20.013 (12) Å
c = 14.329 (12) Å
β = 106.148 (7)°
V = 3210 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 298 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.955, T_max = 0.955
12089 measured reflections
2830 independent reflections
1819 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.090
S = 1.00
2830 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	1.99	2.791 (4)	154
Symmetry code: (i) -x, -y, -z+1.

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: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007441/hy2515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007441/hy2515Isup2.hkl

checkCIF report

Comment top

In recent years many interests have been focused on 2-(naphthalen-1-yl)acetate ligand 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 manganese complexes containing benzimidazole ligands.

In the title mononuclear complex (Fig. 1), the Mn^II ion is located on a twofold rotation axis and six-coordinated by two N-donor atoms from two benzimidazoles and four O-donor atoms from two 2-(naphthalen-1-yl)acetate anions, displaying a distorted MnN₂O₄ octahedral geometry, with Mn—O bond lengths of 2.181 (2) and 2.339 (2) Å and a Mn—N bond length of 2.153 (2) Å. The solvent water molecules could not be modeled as discrete atomic sites. The crystal packing is stabilized by intermolecular N—H···O hydrogen bonds (Table 1), which give rise to a one-dimensional structure (Fig. 2). π–π ineractions between the imidazole rings and between the benzene rings of the 2-(naphthalen-1-yl)acetate ligands [centroid–centroid distances = 3.761 (3) and 3.728 (4) Å] are observed. An analogue cadmium(II) complex has been reported previously (Duan et al., 2007).

Related literature top

For related structures 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 Mn(NO₃)₂.4H₂O (75 mg, 0.3 mmol), 1-naphthylacetic acid (93 mg, 0.5 mmol), benzimidazole (35.4 mg, 0.3 mmol) and NaOH (20 mg, 0.5 mmol) in 16 ml of water/ethanol (v/v 2:1) under solvothermal conditions. The mixture was homogenized and transferred into a sealed Teflon-lined solvothermal bomb (volume: 25 ml) and heated to 160°C for three days. After cooling, colorless crystals of the title compound were obtained, which were washed with distilled water and absolute ethanol (yield: 46.3% based on Mn).

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: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (A) -x, y, 3/2-z.]
	Fig. 2. Part of the one-dimensional structure of the title compound, formed by N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding are omitted for clarity.

Bis(1H-benzimidazole-κN³)bis[2-(naphthalen-1-yl)acetato- κ²O,O']manganese(II) monohydrate top

Crystal data top

[Mn(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O	F(000) = 1372
M_r = 679.62	D_x = 1.369 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1147 reflections
a = 11.654 (7) Å	θ = 2.3–18.0°
b = 20.013 (12) Å	µ = 0.46 mm⁻¹
c = 14.329 (12) Å	T = 298 K
β = 106.148 (7)°	Block, colorless
V = 3210 (4) Å³	0.10 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	1819 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.955, T_max = 0.955	k = −23→23
12089 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0307P)²] where P = (F_o² + 2F_c²)/3
2830 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

[Mn(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O	V = 3210 (4) Å³
M_r = 679.62	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 11.654 (7) Å	µ = 0.46 mm⁻¹
b = 20.013 (12) Å	T = 298 K
c = 14.329 (12) Å	0.10 × 0.10 × 0.10 mm
β = 106.148 (7)°

Data collection top

Bruker APEXII CCD diffractometer	2830 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1819 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.955	R_int = 0.068
12089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2830 reflections	Δρ_min = −0.19 e Å⁻³
213 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
Mn1	0.0000	0.02104 (3)	0.7500	0.0408 (2)
O1	0.18427 (16)	0.04197 (10)	0.83166 (13)	0.0572 (5)
O2	0.11161 (15)	0.10711 (9)	0.70743 (12)	0.0494 (5)
N1	0.01727 (19)	−0.04724 (10)	0.63856 (15)	0.0417 (6)
N2	−0.0295 (2)	−0.09629 (11)	0.49442 (15)	0.0504 (6)
H2	−0.0711	−0.1080	0.4373	0.060*
C1	0.1968 (2)	0.08917 (15)	0.7784 (2)	0.0432 (7)
C2	0.3144 (2)	0.12562 (14)	0.80207 (19)	0.0523 (8)
H2A	0.3178	0.1557	0.8559	0.063*
H2B	0.3780	0.0931	0.8240	0.063*
C3	0.3389 (2)	0.16536 (14)	0.72073 (19)	0.0436 (7)
C4	0.3436 (2)	0.23303 (15)	0.7247 (2)	0.0584 (8)
H4	0.3303	0.2549	0.7780	0.070*
C5	0.3681 (3)	0.27052 (16)	0.6501 (3)	0.0698 (10)
H5	0.3716	0.3169	0.6549	0.084*
C6	0.3868 (3)	0.24044 (18)	0.5716 (3)	0.0679 (9)
H6	0.4023	0.2661	0.5224	0.082*
C7	0.3829 (2)	0.17035 (16)	0.5635 (2)	0.0511 (7)
C8	0.3589 (2)	0.13228 (14)	0.63879 (19)	0.0412 (7)
C9	0.3563 (2)	0.06224 (15)	0.6286 (2)	0.0532 (8)
H9	0.3427	0.0359	0.6779	0.064*
C10	0.3731 (2)	0.03232 (17)	0.5483 (3)	0.0661 (9)
H10	0.3701	−0.0140	0.5431	0.079*
C11	0.3948 (3)	0.0703 (2)	0.4742 (3)	0.0746 (11)
H11	0.4061	0.0494	0.4195	0.090*
C12	0.3995 (3)	0.1376 (2)	0.4811 (2)	0.0671 (9)
H12	0.4139	0.1626	0.4308	0.081*
C13	−0.0650 (2)	−0.05600 (13)	0.5549 (2)	0.0460 (7)
H13	−0.1400	−0.0361	0.5399	0.055*
C14	0.0854 (3)	−0.11580 (13)	0.5397 (2)	0.0449 (7)
C15	0.1141 (2)	−0.08492 (12)	0.63008 (19)	0.0409 (7)
C16	0.2253 (3)	−0.09474 (14)	0.6959 (2)	0.0536 (8)
H16	0.2454	−0.0749	0.7570	0.064*
C17	0.3040 (3)	−0.13490 (16)	0.6668 (3)	0.0680 (9)
H17	0.3795	−0.1421	0.7090	0.082*
C18	0.2742 (3)	−0.16529 (16)	0.5757 (3)	0.0733 (10)
H18	0.3302	−0.1922	0.5586	0.088*
C19	0.1649 (3)	−0.15643 (14)	0.5110 (2)	0.0618 (9)
H19	0.1448	−0.1769	0.4504	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0346 (3)	0.0473 (4)	0.0410 (4)	0.000	0.0109 (3)	0.000
O1	0.0497 (13)	0.0629 (14)	0.0558 (13)	−0.0104 (10)	0.0093 (10)	0.0105 (11)
O2	0.0330 (11)	0.0661 (14)	0.0464 (11)	−0.0017 (9)	0.0065 (9)	0.0026 (10)
N1	0.0402 (14)	0.0450 (14)	0.0393 (13)	0.0013 (11)	0.0101 (11)	0.0001 (11)
N2	0.0587 (17)	0.0528 (16)	0.0371 (13)	−0.0058 (13)	0.0092 (12)	−0.0024 (12)
C1	0.0345 (17)	0.056 (2)	0.0409 (17)	−0.0010 (14)	0.0136 (14)	−0.0100 (15)
C2	0.0361 (16)	0.074 (2)	0.0443 (17)	−0.0125 (15)	0.0076 (13)	−0.0035 (15)
C3	0.0327 (16)	0.0474 (19)	0.0503 (17)	−0.0071 (13)	0.0106 (13)	−0.0003 (15)
C4	0.0475 (19)	0.055 (2)	0.069 (2)	−0.0020 (16)	0.0099 (16)	−0.0101 (18)
C5	0.063 (2)	0.043 (2)	0.094 (3)	−0.0040 (17)	0.007 (2)	0.007 (2)
C6	0.055 (2)	0.072 (3)	0.073 (2)	−0.0055 (18)	0.0113 (18)	0.021 (2)
C7	0.0359 (17)	0.059 (2)	0.0562 (19)	0.0024 (15)	0.0081 (14)	0.0076 (17)
C8	0.0298 (15)	0.0433 (18)	0.0484 (17)	0.0018 (13)	0.0075 (13)	0.0033 (14)
C9	0.0405 (18)	0.052 (2)	0.066 (2)	0.0010 (15)	0.0128 (15)	−0.0006 (16)
C10	0.0413 (19)	0.065 (2)	0.085 (3)	0.0085 (17)	0.0065 (18)	−0.022 (2)
C11	0.045 (2)	0.111 (3)	0.066 (2)	0.017 (2)	0.0111 (18)	−0.018 (2)
C12	0.044 (2)	0.104 (3)	0.052 (2)	0.0104 (19)	0.0117 (16)	0.009 (2)
C13	0.0428 (18)	0.0490 (18)	0.0462 (18)	−0.0002 (14)	0.0124 (15)	0.0027 (14)
C14	0.0521 (19)	0.0386 (17)	0.0484 (18)	−0.0001 (14)	0.0216 (15)	0.0021 (14)
C15	0.0464 (18)	0.0352 (16)	0.0436 (16)	0.0002 (13)	0.0166 (14)	0.0024 (13)
C16	0.050 (2)	0.0483 (19)	0.0581 (19)	0.0027 (15)	0.0084 (16)	0.0032 (15)
C17	0.049 (2)	0.059 (2)	0.094 (3)	0.0127 (17)	0.0150 (19)	0.006 (2)
C18	0.071 (3)	0.054 (2)	0.107 (3)	0.0116 (19)	0.047 (2)	0.003 (2)
C19	0.081 (3)	0.049 (2)	0.066 (2)	−0.0016 (18)	0.038 (2)	−0.0037 (16)

Geometric parameters (Å, º) top

Mn1—N1	2.153 (2)	C7—C12	1.411 (4)
Mn1—O1	2.181 (2)	C7—C8	1.411 (4)
Mn1—O2	2.339 (2)	C8—C9	1.409 (4)
O1—C1	1.248 (3)	C9—C10	1.359 (4)
O2—C1	1.260 (3)	C9—H9	0.9300
N1—C13	1.322 (3)	C10—C11	1.385 (4)
N1—C15	1.391 (3)	C10—H10	0.9300
N2—C13	1.331 (3)	C11—C12	1.350 (4)
N2—C14	1.372 (3)	C11—H11	0.9300
N2—H2	0.8600	C12—H12	0.9300
C1—C2	1.505 (4)	C13—H13	0.9300
C2—C3	1.503 (4)	C14—C19	1.378 (4)
C2—H2A	0.9700	C14—C15	1.390 (3)
C2—H2B	0.9700	C15—C16	1.389 (4)
C3—C4	1.356 (4)	C16—C17	1.369 (4)
C3—C8	1.423 (4)	C16—H16	0.9300
C4—C5	1.398 (4)	C17—C18	1.394 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.346 (4)	C18—C19	1.362 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.407 (4)	C19—H19	0.9300
C6—H6	0.9300

N1ⁱ—Mn1—N1	101.22 (12)	C8—C3—C2	120.3 (2)
N1ⁱ—Mn1—O1	90.30 (8)	C3—C4—C5	121.2 (3)
N1—Mn1—O1	103.80 (8)	C3—C4—H4	119.4
N1ⁱ—Mn1—O1ⁱ	103.80 (8)	C5—C4—H4	119.4
N1—Mn1—O1ⁱ	90.30 (8)	C6—C5—C4	120.9 (3)
O1—Mn1—O1ⁱ	157.86 (11)	C6—C5—H5	119.6
N1ⁱ—Mn1—O2	146.52 (7)	C4—C5—H5	119.6
N1—Mn1—O2	95.77 (8)	C5—C6—C7	120.4 (3)
O1—Mn1—O2	57.50 (7)	C5—C6—H6	119.8
O1ⁱ—Mn1—O2	104.75 (8)	C7—C6—H6	119.8
N1ⁱ—Mn1—O2ⁱ	95.77 (8)	C6—C7—C12	121.6 (3)
N1—Mn1—O2ⁱ	146.52 (7)	C6—C7—C8	118.9 (3)
O1—Mn1—O2ⁱ	104.75 (8)	C12—C7—C8	119.4 (3)
O1ⁱ—Mn1—O2ⁱ	57.50 (7)	C9—C8—C7	117.5 (3)
O2—Mn1—O2ⁱ	85.16 (10)	C9—C8—C3	123.0 (3)
N1ⁱ—Mn1—C1ⁱ	100.87 (8)	C7—C8—C3	119.5 (3)
N1—Mn1—C1ⁱ	118.47 (9)	C10—C9—C8	121.5 (3)
O1—Mn1—C1ⁱ	132.61 (10)	C10—C9—H9	119.3
O1ⁱ—Mn1—C1ⁱ	28.56 (7)	C8—C9—H9	119.3
O2—Mn1—C1ⁱ	95.93 (9)	C9—C10—C11	120.5 (3)
O2ⁱ—Mn1—C1ⁱ	28.94 (7)	C9—C10—H10	119.7
N1ⁱ—Mn1—C1	118.47 (9)	C11—C10—H10	119.7
N1—Mn1—C1	100.86 (8)	C12—C11—C10	120.2 (3)
O1—Mn1—C1	28.56 (7)	C12—C11—H11	119.9
O1ⁱ—Mn1—C1	132.61 (10)	C10—C11—H11	119.9
O2—Mn1—C1	28.94 (7)	C11—C12—C7	120.8 (3)
O2ⁱ—Mn1—C1	95.93 (9)	C11—C12—H12	119.6
C1ⁱ—Mn1—C1	116.79 (13)	C7—C12—H12	119.6
C1—O1—Mn1	94.76 (16)	N1—C13—N2	113.1 (3)
C1—O2—Mn1	87.15 (17)	N1—C13—H13	123.4
C13—N1—C15	104.5 (2)	N2—C13—H13	123.4
C13—N1—Mn1	124.24 (19)	N2—C14—C19	132.5 (3)
C15—N1—Mn1	130.88 (17)	N2—C14—C15	105.3 (2)
C13—N2—C14	107.7 (2)	C19—C14—C15	122.1 (3)
C13—N2—H2	126.2	C16—C15—C14	120.5 (3)
C14—N2—H2	126.2	C16—C15—N1	130.1 (3)
O1—C1—O2	120.6 (2)	C14—C15—N1	109.4 (2)
O1—C1—C2	118.9 (2)	C17—C16—C15	117.0 (3)
O2—C1—C2	120.5 (3)	C17—C16—H16	121.5
O1—C1—Mn1	56.68 (13)	C15—C16—H16	121.5
O2—C1—Mn1	63.91 (14)	C16—C17—C18	121.9 (3)
C2—C1—Mn1	175.6 (2)	C16—C17—H17	119.0
C3—C2—C1	116.1 (2)	C18—C17—H17	119.0
C3—C2—H2A	108.3	C19—C18—C17	121.5 (3)
C1—C2—H2A	108.3	C19—C18—H18	119.3
C3—C2—H2B	108.3	C17—C18—H18	119.3
C1—C2—H2B	108.3	C18—C19—C14	117.0 (3)
H2A—C2—H2B	107.4	C18—C19—H19	121.5
C4—C3—C8	119.0 (3)	C14—C19—H19	121.5
C4—C3—C2	120.7 (3)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱⁱ	0.86	1.99	2.791 (4)	154

Symmetry code: (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O
M_r	679.62
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	11.654 (7), 20.013 (12), 14.329 (12)
β (°)	106.148 (7)
V (Å³)	3210 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	12089, 2830, 1819
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.090, 1.00
No. of reflections	2830
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	1.99	2.791 (4)	154

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

The authors thank China University of Mining & Technology, Xuzhou, and Huaihai Institute of Technology for support of this work.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duan, J.-G., Liu, J.-W. & Wu, S. (2007). Acta Cryst. E63, m692–m694. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ji, L.-L., Liu, J.-S. & Song, W.-D. (2011). Acta Cryst. E67, m606. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, D.-X., Feng, L.-X. & Zhang, X.-Q. (2006). Chin. J. Inorg. Chem. 22, 1891–1894. CAS Google Scholar
Yang, Y.-Q., Li, C.-H., Li, W. & Kuang, Y.-F. (2008). Chin. J. Struct. Chem. 27, 404–408. CAS Google Scholar
Yin, F.-J., Han, L.-J., Yang, S.-P. & Xu, X. Y. (2011). Acta Cryst. E67, m1772. Web of Science CSD CrossRef IUCr Journals Google Scholar

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