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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page m1772
https://doi.org/10.1107/S1600536811047969

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

Fu-Jun Yin,a* Li-Jun Han,b Shu-Ping Yangc and Xing You Xud

aJiangsu Marine Resources Development Research Institute, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, bDepartment of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, cDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, and dHuaiyin Insititute of Technology, Huaiyin 223003, People's Republic of China
*Correspondence e-mail: yfj1999@126.com

(Received 8 November 2011; accepted 11 November 2011; online 16 November 2011)

In the crystal structure of the title compound, [Cu(C12H9O2)2(C4H6N2)2], the Cu(II) cations are square-planar coordinated by two 1-naphthyl­acetate anions and two 2-methyl-imidazole ligands into discrete complexes that are located on centres of inversion. These complexes are linked into chains parallel to [010] by inter­molecular N—H⋯O hydrogen bonding between the N—H H atom of the 2-methyl-imidazole ligands and the carboxyl­ate O atoms that are not involved in metal coordination.

Related literature

For related structures, see: Liu et al. (2007[Liu, Y.-F., Xia, H.-T., Wang, D.-Q., Yang, S.-P. & Meng, Y.-L. (2007). Acta Cryst. E63, m2544.]); Chen et al. (2004[Chen, L.-F., Zhang, J., Song, L.-J., Wang, W.-G. & Ju, Z.-F. (2004). Acta Cryst. E60, m1032-m1034.]); Yang et al. (2008[Yang, Y.-Q., Li, C.-H. L. W. & Kuang, Y.-F. (2008). Chin. J. Struct. Chem. 30, 4524-4530.]); Tang et al. (2006[Tang, D.-X., Feng, L.-X. & Zhang, X.-Q. (2006). Chin. J. Inorg. Chem. 22, 1891-1894.]); Ji et al. (2011[Ji, L.-L., Liu, J.-S. & Song, W.-D. (2011). Acta Cryst. E67, m606.]).

[Scheme 1]

Experimental

Crystal data

  • [Cu(C12H9O2)2(C4H6N2)2]

  • Mr = 598.14

  • Monoclinic, C 2/c

  • a = 28.430 (4) Å

  • b = 7.5544 (10) Å

  • c = 13.9417 (19) Å

  • β = 108.216 (2)°

  • V = 2844.2 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.81 mm−1

  • T = 298 K

  • 0.12 × 0.10 × 0.10 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.866, Tmax = 0.903

  • 10438 measured reflections

  • 2507 independent reflections

  • 2081 reflections with I > 2σ(I)

  • Rint = 0.032
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.090

  • S = 1.05

  • 2507 reflections

  • 188 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.22 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 1.97 2.775 (3) 155
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047969/nc2255sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047969/nc2255Isup2.hkl

checkCIF report


Comment top

The crystal structure of the title compound was determined as part of an ongoing study on the structural properties of copper complexes containing imidazole ligands. In this study 1-naphthylacetate was used as ligand, for which only a few metal complexes were reported (Liu et al.,2007; Chen et al., 2004; Yang et al., 2008; Tang et al.,2006 ; Ji et al.,2011).

In the crystal structure of the title compound [Cu(C12H9O2)2(C4H6N2)2], each copper cation are coordinated by two N atoms of two symmetry equivalent 2-methyl-1H-imidazole ligands and by two carboxyl O atoms of two symmetry related 1-naphthylacetate anions within a square planar coordination (Fig. 1). The Cu—N and Cu—O bond lengths are 1.9750 (18) and 1.9791 (16) Å, respectively. The asymmetric unit consits of one Cu(II) cation that is located on a center of inversion as well of one neutral and one anionic ligand in general positions. The discrete complexes are linked into chains by N—H···O hydrogen bonding (Fig. 2 and Table 1).

Related literature top

For related structures, see: Liu et al. (2007); Chen et al. (2004); Yang et al. (2008); Tang et al. (2006); Ji et al. (2011).

Experimental top

The title compound was synthesized by the reaction of Cu(NO3)2.3 H2O (72.3 mg, 0.3 mmol), 1-naphthylacetic acid (93 mg, 0.5 mmol), 2-methylimidazole (32.8 mg, 0.4 mmol) and NaOH (20 mg, 0.5 mmol) in 4 mL of a water-ethanol mixture (volume ratio = 1:1 of water:ethanol) under solvothermal conditions. The starting mixture was homogenized and transferred into a sealed teflon-lined solvothermal bomb (volume: 25 ml) and heated at 140° for three days. After cooling green crystals of the title compound were obtained, which were washed with distilled water and absolute ethyl alcohol (yield: 44.6% based on Cu(NO3)2.3 H2O ).

Refinement top

The C-H H atoms were positioned with idealized geometry (methyl H atoms allowed to rotatae but not to tip) and were refined with Uiso(H) =1.2Ueq(C)] (1.5 for methyl H atoms) using a riding model.

Structure description top

The crystal structure of the title compound was determined as part of an ongoing study on the structural properties of copper complexes containing imidazole ligands. In this study 1-naphthylacetate was used as ligand, for which only a few metal complexes were reported (Liu et al.,2007; Chen et al., 2004; Yang et al., 2008; Tang et al.,2006 ; Ji et al.,2011).

In the crystal structure of the title compound [Cu(C12H9O2)2(C4H6N2)2], each copper cation are coordinated by two N atoms of two symmetry equivalent 2-methyl-1H-imidazole ligands and by two carboxyl O atoms of two symmetry related 1-naphthylacetate anions within a square planar coordination (Fig. 1). The Cu—N and Cu—O bond lengths are 1.9750 (18) and 1.9791 (16) Å, respectively. The asymmetric unit consits of one Cu(II) cation that is located on a center of inversion as well of one neutral and one anionic ligand in general positions. The discrete complexes are linked into chains by N—H···O hydrogen bonding (Fig. 2 and Table 1).

For related structures, see: Liu et al. (2007); Chen et al. (2004); Yang et al. (2008); Tang et al. (2006); Ji et al. (2011).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level. Symmetry code: i= -x + 1, -y, -z + 2)
[Figure 2] Fig. 2. Part of the crystal structure of the title compound. Hydrogen bonding is shown as dashed lines and H atoms not involved in hydrogen bonding are omitted for clarity.
Bis(2-methyl-1H-imidazole-κN3)bis[2-(naphthalen-1- yl)acetato-κO]copper(II) top
Crystal data top
[Cu(C12H9O2)2(C4H6N2)2]F(000) = 1244
Mr = 598.14Dx = 1.397 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2712 reflections
a = 28.430 (4) Åθ = 2.8–22.8°
b = 7.5544 (10) ŵ = 0.81 mm−1
c = 13.9417 (19) ÅT = 298 K
β = 108.216 (2)°Block, green
V = 2844.2 (7) Å30.12 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		2507 independent reflections
Radiation source: fine-focus sealed tube2081 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −33→33
Tmin = 0.866, Tmax = 0.903k = −8→8
10438 measured reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0424P)2 + 2.2367P]
where P = (Fo2 + 2Fc2)/3
2507 reflections(Δ/σ)max < 0.001
188 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
[Cu(C12H9O2)2(C4H6N2)2]V = 2844.2 (7) Å3
Mr = 598.14Z = 4
Monoclinic, C2/cMo Kα radiation
a = 28.430 (4) ŵ = 0.81 mm−1
b = 7.5544 (10) ÅT = 298 K
c = 13.9417 (19) Å0.12 × 0.10 × 0.10 mm
β = 108.216 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		2507 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2081 reflections with I > 2σ(I)
Tmin = 0.866, Tmax = 0.903Rint = 0.032
10438 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.05Δρmax = 0.23 e Å−3
2507 reflectionsΔρmin = −0.22 e Å−3
188 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
xyzUiso*/Ueq
C10.41432 (9)0.1140 (3)0.87770 (18)0.0393 (5)
C20.36810 (9)0.1271 (3)0.78610 (19)0.0444 (6)
H2A0.34210.18500.80590.053*
H2B0.37540.20040.73540.053*
C30.34946 (8)−0.0505 (3)0.74014 (17)0.0387 (5)
C40.35305 (9)−0.0972 (4)0.64815 (18)0.0488 (6)
H40.3677−0.01900.61440.059*
C50.33521 (10)−0.2605 (4)0.6031 (2)0.0586 (7)
H50.3384−0.28950.54060.070*
C60.31340 (10)−0.3760 (4)0.6506 (2)0.0553 (7)
H60.3011−0.48290.61980.066*
C70.30908 (8)−0.3357 (3)0.74649 (18)0.0414 (6)
C80.32775 (8)−0.1709 (3)0.79265 (16)0.0356 (5)
C90.32324 (9)−0.1349 (3)0.88921 (18)0.0442 (6)
H90.3357−0.02930.92160.053*
C100.30110 (10)−0.2521 (4)0.9353 (2)0.0561 (7)
H100.2985−0.22530.99850.067*
C110.28210 (10)−0.4129 (4)0.8889 (2)0.0587 (7)
H110.2666−0.49110.92080.070*
C120.28645 (9)−0.4541 (4)0.7972 (2)0.0521 (7)
H120.2743−0.56180.76730.062*
C130.54765 (9)0.2344 (3)0.88513 (18)0.0453 (6)
H130.54090.15550.83130.054*
C140.57019 (10)0.3915 (3)0.8895 (2)0.0509 (7)
H140.58170.44160.84010.061*
C150.55191 (8)0.3503 (3)1.02945 (18)0.0381 (5)
C160.54798 (10)0.3857 (3)1.13113 (19)0.0500 (6)
H16A0.52120.31791.14040.075*
H16B0.54190.50951.13740.075*
H16C0.57840.35271.18150.075*
N10.53589 (7)0.2080 (2)0.97253 (14)0.0378 (5)
N20.57289 (8)0.4629 (3)0.98082 (16)0.0453 (5)
H20.58590.56331.00360.054*
O10.44990 (6)0.0258 (2)0.86540 (12)0.0421 (4)
O20.41557 (7)0.1856 (2)0.95858 (13)0.0522 (5)
Cu10.50000.00001.00000.03683 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0456 (14)0.0263 (11)0.0454 (14)−0.0092 (10)0.0134 (11)0.0017 (10)
C20.0460 (14)0.0365 (13)0.0504 (15)0.0049 (11)0.0146 (12)0.0092 (11)
C30.0285 (12)0.0464 (14)0.0374 (13)0.0043 (10)0.0051 (10)0.0046 (10)
C40.0409 (14)0.0658 (17)0.0397 (14)−0.0029 (13)0.0125 (11)0.0072 (13)
C50.0520 (16)0.082 (2)0.0439 (15)−0.0064 (15)0.0177 (13)−0.0145 (15)
C60.0461 (15)0.0595 (17)0.0565 (17)−0.0061 (13)0.0106 (13)−0.0200 (14)
C70.0299 (12)0.0470 (14)0.0442 (14)−0.0005 (10)0.0072 (10)−0.0022 (11)
C80.0250 (11)0.0424 (13)0.0361 (12)0.0044 (9)0.0045 (9)0.0026 (10)
C90.0411 (14)0.0503 (15)0.0392 (13)−0.0011 (11)0.0098 (11)−0.0009 (11)
C100.0477 (15)0.080 (2)0.0413 (15)−0.0057 (14)0.0151 (12)0.0059 (14)
C110.0431 (15)0.0704 (19)0.0611 (18)−0.0101 (14)0.0143 (13)0.0161 (16)
C120.0367 (14)0.0507 (16)0.0617 (18)−0.0076 (11)0.0052 (12)0.0022 (13)
C130.0504 (15)0.0453 (14)0.0417 (14)−0.0035 (12)0.0167 (12)−0.0097 (11)
C140.0587 (17)0.0489 (15)0.0517 (16)−0.0046 (13)0.0266 (13)−0.0030 (12)
C150.0334 (12)0.0346 (12)0.0441 (13)0.0019 (10)0.0090 (10)−0.0045 (10)
C160.0597 (16)0.0451 (15)0.0454 (15)0.0053 (12)0.0169 (13)−0.0084 (12)
N10.0364 (11)0.0340 (10)0.0414 (11)−0.0033 (8)0.0098 (9)−0.0055 (9)
N20.0486 (12)0.0337 (11)0.0555 (13)−0.0086 (9)0.0190 (10)−0.0074 (9)
O10.0368 (9)0.0444 (10)0.0412 (9)−0.0025 (7)0.0065 (7)−0.0054 (7)
O20.0678 (12)0.0392 (9)0.0518 (11)−0.0075 (8)0.0219 (9)−0.0115 (8)
Cu10.0348 (2)0.0341 (2)0.0391 (2)−0.00479 (17)0.00786 (17)−0.00590 (17)
Geometric parameters (Å, º) top
C1—O21.241 (3)C10—H100.9300
C1—O11.267 (3)C11—C121.358 (4)
C1—C21.523 (3)C11—H110.9300
C2—C31.510 (3)C12—H120.9300
C2—H2A0.9700C13—C141.341 (3)
C2—H2B0.9700C13—N11.375 (3)
C3—C41.364 (3)C13—H130.9300
C3—C81.424 (3)C14—N21.363 (3)
C4—C51.405 (4)C14—H140.9300
C4—H40.9300C15—N11.329 (3)
C5—C61.358 (4)C15—N21.339 (3)
C5—H50.9300C15—C161.481 (3)
C6—C71.413 (3)C16—H16A0.9600
C6—H60.9300C16—H16B0.9600
C7—C121.413 (3)C16—H16C0.9600
C7—C81.425 (3)N1—Cu11.9750 (18)
C8—C91.418 (3)N2—H20.8600
C9—C101.358 (3)O1—Cu11.9791 (16)
C9—H90.9300Cu1—N1i1.9750 (18)
C10—C111.402 (4)Cu1—O1i1.9791 (16)
O2—C1—O1123.7 (2)C12—C11—H11120.1
O2—C1—C2120.4 (2)C10—C11—H11120.1
O1—C1—C2115.9 (2)C11—C12—C7121.0 (3)
C3—C2—C1113.22 (18)C11—C12—H12119.5
C3—C2—H2A108.9C7—C12—H12119.5
C1—C2—H2A108.9C14—C13—N1109.5 (2)
C3—C2—H2B108.9C14—C13—H13125.3
C1—C2—H2B108.9N1—C13—H13125.2
H2A—C2—H2B107.7C13—C14—N2106.2 (2)
C4—C3—C8119.3 (2)C13—C14—H14126.9
C4—C3—C2120.6 (2)N2—C14—H14126.9
C8—C3—C2120.1 (2)N1—C15—N2109.6 (2)
C3—C4—C5121.6 (2)N1—C15—C16127.1 (2)
C3—C4—H4119.2N2—C15—C16123.3 (2)
C5—C4—H4119.2C15—C16—H16A109.5
C6—C5—C4120.2 (2)C15—C16—H16B109.5
C6—C5—H5119.9H16A—C16—H16B109.5
C4—C5—H5119.9C15—C16—H16C109.5
C5—C6—C7120.8 (2)H16A—C16—H16C109.5
C5—C6—H6119.6H16B—C16—H16C109.5
C7—C6—H6119.6C15—N1—C13106.20 (19)
C6—C7—C12121.6 (2)C15—N1—Cu1128.97 (16)
C6—C7—C8119.0 (2)C13—N1—Cu1124.80 (15)
C12—C7—C8119.3 (2)C15—N2—C14108.5 (2)
C9—C8—C3123.2 (2)C15—N2—H2125.6
C9—C8—C7117.7 (2)C14—N2—H2125.9
C3—C8—C7119.1 (2)C1—O1—Cu1106.96 (15)
C10—C9—C8121.1 (2)N1—Cu1—N1i180.00 (11)
C10—C9—H9119.4N1—Cu1—O1i89.99 (7)
C8—C9—H9119.4N1i—Cu1—O1i90.01 (7)
C9—C10—C11121.0 (3)N1—Cu1—O190.01 (7)
C9—C10—H10119.5N1i—Cu1—O189.99 (7)
C11—C10—H10119.5O1i—Cu1—O1180.000 (1)
C12—C11—C10119.8 (3)
O2—C1—C2—C3−127.3 (2)C10—C11—C12—C7−1.2 (4)
O1—C1—C2—C352.1 (3)C6—C7—C12—C11−179.3 (3)
C1—C2—C3—C4−110.1 (3)C8—C7—C12—C110.2 (4)
C1—C2—C3—C870.1 (3)N1—C13—C14—N20.5 (3)
C8—C3—C4—C50.9 (4)N2—C15—N1—C130.1 (3)
C2—C3—C4—C5−178.9 (2)C16—C15—N1—C13179.9 (2)
C3—C4—C5—C60.5 (4)N2—C15—N1—Cu1−177.75 (15)
C4—C5—C6—C7−1.2 (4)C16—C15—N1—Cu12.1 (4)
C5—C6—C7—C12179.9 (3)C14—C13—N1—C15−0.4 (3)
C5—C6—C7—C80.4 (4)C14—C13—N1—Cu1177.56 (17)
C4—C3—C8—C9178.9 (2)N1—C15—N2—C140.2 (3)
C2—C3—C8—C9−1.3 (3)C16—C15—N2—C14−179.6 (2)
C4—C3—C8—C7−1.6 (3)C13—C14—N2—C15−0.5 (3)
C2—C3—C8—C7178.2 (2)O2—C1—O1—Cu17.9 (3)
C6—C7—C8—C9−179.5 (2)C2—C1—O1—Cu1−171.46 (15)
C12—C7—C8—C91.0 (3)C15—N1—Cu1—O1i−50.3 (2)
C6—C7—C8—C31.0 (3)C13—N1—Cu1—O1i132.28 (19)
C12—C7—C8—C3−178.5 (2)C15—N1—Cu1—O1129.7 (2)
C3—C8—C9—C10178.3 (2)C13—N1—Cu1—O1−47.72 (19)
C7—C8—C9—C10−1.2 (3)C1—O1—Cu1—N1−95.44 (14)
C8—C9—C10—C110.2 (4)C1—O1—Cu1—N1i84.56 (14)
C9—C10—C11—C121.0 (4)
Symmetry code: (i) −x+1, −y, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2ii0.861.972.775 (3)155
Symmetry code: (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula[Cu(C12H9O2)2(C4H6N2)2]
Mr598.14
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)28.430 (4), 7.5544 (10), 13.9417 (19)
β (°) 108.216 (2)
V (Å3)2844.2 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.81
Crystal size (mm)0.12 × 0.10 × 0.10
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.866, 0.903
No. of measured, independent and
observed [I > 2σ(I)] reflections		10438, 2507, 2081
Rint0.032
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.090, 1.05
No. of reflections2507
No. of parameters188
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.22

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.861.9732.775 (3)154.7
Symmetry code: (i) −x+1, −y+1, −z+2.
 

References

First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChen, L.-F., Zhang, J., Song, L.-J., Wang, W.-G. & Ju, Z.-F. (2004). Acta Cryst. E60, m1032–m1034.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationJi, L.-L., Liu, J.-S. & Song, W.-D. (2011). Acta Cryst. E67, m606.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLiu, Y.-F., Xia, H.-T., Wang, D.-Q., Yang, S.-P. & Meng, Y.-L. (2007). Acta Cryst. E63, m2544.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTang, D.-X., Feng, L.-X. & Zhang, X.-Q. (2006). Chin. J. Inorg. Chem. 22, 1891–1894.  CAS Google Scholar
 First citationYang, Y.-Q., Li, C.-H. L. W. & Kuang, Y.-F. (2008). Chin. J. Struct. Chem. 30, 4524–4530.  Google Scholar

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page m1772
https://doi.org/10.1107/S1600536811047969
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