Bis(nitrato-κO)[(S)-2-(pyrrolidin-2-yl)-1H-benzimidazole]cadmium(II)

Dai, W.; Fu, D.-W.

doi:10.1107/S1600536808006454

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1017

doi:10.1107/S1600536808006454

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Bis(nitrato-κO)[(S)-2-(pyrrolidin-2-yl)-1H-benzimidazole]cadmium(II)

Wei Dai ^a and Da-Wei Fu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 24 January 2008; accepted 31 March 2008; online 9 July 2008)

The title compound, [Cd(NO₃)₂(C₁₁H₁₃N₃)₂], was synthesized by hydrothermal reaction of Cd(NO₃)₂ and S-2-(pyrrolidin-2-yl)-1H-1,3-benzimidazole. The Cd atom lies on an inversion centre. The distorted octahedral Cd environment contains two planar trans-related N,N-chelating S-2-(pyrrolidin-2-yl)-1H-1,3-benzimidazole ligands in one plane and two monodentate nitrate ligands. N—H⋯O hydrogen bonds involving a nitrate O atom build up an infinite chain parallel to the a axis.

Related literature

For physical properties such as fluorescence and dielectric behaviors of metal–organic coordination compounds, see: Aminabhavi et al. (1986 ); Ye et al. (2008 ).

Experimental

Crystal data

[Cd(NO₃)₂(C₁₁H₁₂N₃)₂]
M_r = 610.91
Triclinic, $[P \overline 1]$
a = 8.1487 (16) Å
b = 9.1459 (18) Å
c = 9.7439 (19) Å
α = 111.67 (3)°
β = 112.32 (3)°
γ = 93.80 (3)°
V = 606.0 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.889, T_max = 0.944
6172 measured reflections
2692 independent reflections
2258 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.114
S = 1.07
2692 reflections
169 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1ⁱ	0.91	2.21	2.975 (7)	141
N1—H1A⋯O2ⁱⁱ	0.86	2.03	2.889 (5)	174
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006454/dn2315sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006454/dn2315Isup2.hkl

checkCIF report

Comment top

Metal-organic coordination compounds provide a class of complexes displaying interesting chemical and physical properties such as fluorescence and dielectric behaviors (Aminabhavi et al., 1986; Ye et al., 2008). There has been very strong interest in employing crystal-engineering strategies to generate desirable materials by the hydrothermal reaction. Here we report the synthesis and crystal structure of the title compound Nitrate-(S-2-(pyrrolidin-2-yl)-1H-benzo[d]imidazole)-Cadmium).

In the title compound, the cadmium atom lies on an inversion centre. The distorted octahedral Cd environment contains two planar trans-related N,N-chelating S-2-(pyrrolidin-2-yl)-1H-benzo imidazole in one plane and two monodentate nitrate (Fig. 1). N—H···O hydrogen bonds involving one O atom of the nitrate build up an infinite chain developing parallel to the a axis (Table 1).

Related literature top

For physical properties such as fluorescence and dielectric behaviors of metal–organic coordination compounds, see: Aminabhavi et al. (1986); Ye et al. (2008).

Experimental top

The homochiral ligand S-2-(pyrrolidin-2-yl)-1H-benzo[d]imidazole was synthesized by reaction of S-pyrrolidine-2-carboxylic acid and benzene-1,2-diamine according to the procedure described in the literature(Aminabhavi, et al.(1986)). A mixture of S-2-(pyrrolidin-2-yl)-1H-benzo[d]imidazole(0.1 mmol) and Cd(NO₃)₂ (0.1 mmol) and water (1 ml) sealed in a glass tube were maintained at 70 °C. Crystals suitable for X-ray analysis were obtained after 3 days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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

	Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the c axis and all hydrogen atoms not involved in hydrogen bonding (dashed lines) were omitted for clarity.

Bis(nitrato-κO)[(S)-2-(pyrrolidin-2-yl)-1H- benzimidazole]cadmium(II) top

Crystal data top

[Cd(NO₃)₂(C₁₁H₁₂N₃)₂]	Z = 1
M_r = 610.91	F(000) = 310
Triclinic, P1	D_x = 1.674 Mg m⁻³
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1487 (16) Å	Cell parameters from 2061 reflections
b = 9.1459 (18) Å	θ = 3.3–27.5°
c = 9.7439 (19) Å	µ = 0.96 mm⁻¹
α = 111.67 (3)°	T = 293 K
β = 112.32 (3)°	Prism, colorless
γ = 93.80 (3)°	0.12 × 0.10 × 0.06 mm
V = 606.0 (2) Å³

Data collection top

Rigaku Mercury2 diffractometer	2692 independent reflections
Radiation source: fine-focus sealed tube	2258 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.3°, θ_min = 3.3°
CCD profile fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
T_min = 0.889, T_max = 0.944	l = −12→12
6172 measured 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0464P)² + 0.245P] where P = (F_o² + 2F_c²)/3
2692 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Cd(NO₃)₂(C₁₁H₁₂N₃)₂]	γ = 93.80 (3)°
M_r = 610.91	V = 606.0 (2) Å³
Triclinic, P1	Z = 1
a = 8.1487 (16) Å	Mo Kα radiation
b = 9.1459 (18) Å	µ = 0.96 mm⁻¹
c = 9.7439 (19) Å	T = 293 K
α = 111.67 (3)°	0.12 × 0.10 × 0.06 mm
β = 112.32 (3)°

Data collection top

Rigaku Mercury2 diffractometer	2692 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2258 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.944	R_int = 0.057
6172 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.07	Δρ_max = 0.69 e Å⁻³
2692 reflections	Δρ_min = −0.45 e Å⁻³
169 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

	x	y	z	U_iso*/U_eq
Cd1	0.0000	0.5000	0.0000	0.03774 (18)
O1	0.1413 (6)	0.8668 (6)	−0.0027 (6)	0.0919 (14)
O2	0.2395 (5)	0.7989 (5)	−0.1864 (5)	0.0701 (11)
O3	0.1342 (6)	0.6144 (5)	−0.1353 (5)	0.0730 (11)
N4	0.1714 (5)	0.7596 (6)	−0.1065 (5)	0.0503 (10)
N3	0.0853 (6)	0.2624 (5)	−0.1240 (5)	0.0585 (11)
H3B	0.0050	0.1820	−0.1322	0.070*
N2	0.2902 (4)	0.5267 (4)	0.1908 (4)	0.0376 (8)
N1	0.5347 (5)	0.4236 (5)	0.2503 (5)	0.0470 (9)
H1A	0.6040	0.3577	0.2384	0.056*
C3	0.5789 (7)	0.8578 (6)	0.6093 (6)	0.0557 (13)
H3A	0.5818	0.9564	0.6869	0.067*
C5	0.7348 (6)	0.6476 (6)	0.5341 (5)	0.0453 (11)
H5A	0.8365	0.6041	0.5576	0.054*
C6	0.5793 (6)	0.5690 (5)	0.3855 (5)	0.0376 (9)
C4	0.7314 (7)	0.7920 (6)	0.6443 (6)	0.0522 (12)
H4A	0.8331	0.8476	0.7448	0.063*
C7	0.3627 (6)	0.4036 (6)	0.1402 (5)	0.0444 (11)
C2	0.4236 (6)	0.7797 (6)	0.4619 (6)	0.0487 (11)
H2A	0.3221	0.8238	0.4398	0.058*
C8	0.2668 (7)	0.2502 (6)	−0.0174 (6)	0.0524 (12)
H8A	0.2472	0.1603	0.0108	0.063*
C10	0.2213 (6)	0.1190 (6)	−0.2943 (6)	0.0543 (13)
H10A	0.2635	0.1286	−0.3719	0.065*
H10B	0.1804	0.0053	−0.3229	0.065*
C9	0.3685 (7)	0.2075 (8)	−0.1197 (6)	0.0741 (18)
H9A	0.4472	0.1382	−0.0909	0.089*
H9B	0.4424	0.3042	−0.1055	0.089*
C11	0.0726 (9)	0.2075 (9)	−0.2880 (6)	0.085 (2)
H11A	0.0886	0.2992	−0.3131	0.102*
H11B	−0.0463	0.1356	−0.3678	0.102*
C1	0.4241 (6)	0.6332 (5)	0.3478 (5)	0.0360 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0274 (3)	0.0437 (3)	0.0305 (3)	0.00864 (18)	0.00878 (18)	0.00795 (19)
O1	0.084 (3)	0.095 (3)	0.080 (3)	0.020 (3)	0.050 (3)	0.005 (3)
O2	0.073 (3)	0.080 (3)	0.092 (3)	0.040 (2)	0.048 (2)	0.057 (2)
O3	0.074 (3)	0.077 (3)	0.092 (3)	0.021 (2)	0.050 (2)	0.045 (2)
N4	0.032 (2)	0.071 (3)	0.046 (2)	0.022 (2)	0.0137 (18)	0.024 (2)
N3	0.043 (2)	0.060 (3)	0.048 (2)	0.012 (2)	0.016 (2)	0.003 (2)
N2	0.0310 (19)	0.044 (2)	0.0297 (17)	0.0114 (15)	0.0110 (15)	0.0098 (15)
N1	0.039 (2)	0.060 (3)	0.044 (2)	0.0233 (18)	0.0198 (18)	0.0208 (19)
C3	0.054 (3)	0.051 (3)	0.040 (3)	0.009 (2)	0.011 (2)	0.008 (2)
C5	0.034 (2)	0.060 (3)	0.041 (2)	0.015 (2)	0.010 (2)	0.027 (2)
C6	0.036 (2)	0.044 (2)	0.032 (2)	0.0081 (18)	0.0126 (19)	0.0183 (19)
C4	0.044 (3)	0.060 (3)	0.034 (2)	0.005 (2)	0.004 (2)	0.016 (2)
C7	0.043 (3)	0.054 (3)	0.035 (2)	0.017 (2)	0.017 (2)	0.018 (2)
C2	0.039 (3)	0.054 (3)	0.044 (3)	0.019 (2)	0.014 (2)	0.015 (2)
C8	0.050 (3)	0.055 (3)	0.044 (3)	0.020 (2)	0.017 (2)	0.015 (2)
C10	0.046 (3)	0.065 (3)	0.036 (3)	0.017 (2)	0.016 (2)	0.007 (2)
C9	0.044 (3)	0.108 (5)	0.038 (3)	0.023 (3)	0.013 (2)	0.002 (3)
C11	0.081 (4)	0.113 (5)	0.034 (3)	0.062 (4)	0.016 (3)	0.008 (3)
C1	0.031 (2)	0.044 (2)	0.033 (2)	0.0113 (18)	0.0107 (18)	0.0181 (19)

Geometric parameters (Å, º) top

Cd1—N2ⁱ	2.314 (3)	C3—H3A	0.9300
Cd1—N2	2.314 (3)	C5—C4	1.370 (7)
Cd1—N3ⁱ	2.359 (4)	C5—C6	1.391 (6)
Cd1—N3	2.359 (4)	C5—H5A	0.9300
Cd1—O3	2.448 (4)	C6—C1	1.409 (6)
Cd1—O3ⁱ	2.448 (4)	C4—H4A	0.9300
O1—N4	1.238 (5)	C7—C8	1.513 (7)
O2—N4	1.245 (5)	C2—C1	1.391 (6)
O3—N4	1.241 (5)	C2—H2A	0.9300
N3—C11	1.447 (7)	C8—C9	1.488 (7)
N3—C8	1.490 (6)	C8—H8A	0.9800
N3—H3B	0.9100	C10—C11	1.509 (7)
N2—C7	1.327 (6)	C10—C9	1.514 (7)
N2—C1	1.403 (5)	C10—H10A	0.9700
N1—C7	1.352 (6)	C10—H10B	0.9700
N1—C6	1.384 (6)	C9—H9A	0.9700
N1—H1A	0.8600	C9—H9B	0.9700
C3—C2	1.385 (7)	C11—H11A	0.9700
C3—C4	1.397 (7)	C11—H11B	0.9700

N2ⁱ—Cd1—N2	180.00 (18)	N1—C6—C1	105.2 (4)
N2ⁱ—Cd1—N3ⁱ	75.24 (13)	C5—C6—C1	122.3 (4)
N2—Cd1—N3ⁱ	104.76 (13)	C5—C4—C3	121.6 (4)
N2ⁱ—Cd1—N3	104.76 (13)	C5—C4—H4A	119.2
N2—Cd1—N3	75.24 (13)	C3—C4—H4A	119.2
N3ⁱ—Cd1—N3	180.0	N2—C7—N1	112.7 (4)
N2ⁱ—Cd1—O3	90.22 (13)	N2—C7—C8	125.9 (4)
N2—Cd1—O3	89.78 (13)	N1—C7—C8	121.4 (4)
N3ⁱ—Cd1—O3	94.44 (15)	C3—C2—C1	117.9 (4)
N3—Cd1—O3	85.56 (15)	C3—C2—H2A	121.1
N2ⁱ—Cd1—O3ⁱ	89.78 (13)	C1—C2—H2A	121.1
N2—Cd1—O3ⁱ	90.22 (13)	N3—C8—C9	106.3 (4)
N3ⁱ—Cd1—O3ⁱ	85.56 (15)	N3—C8—C7	111.2 (4)
N3—Cd1—O3ⁱ	94.44 (15)	C9—C8—C7	114.6 (5)
O3—Cd1—O3ⁱ	180.0	N3—C8—H8A	108.2
N4—O3—Cd1	126.5 (3)	C9—C8—H8A	108.2
O1—N4—O3	122.5 (5)	C7—C8—H8A	108.2
O1—N4—O2	118.7 (5)	C11—C10—C9	101.8 (4)
O3—N4—O2	118.9 (4)	C11—C10—H10A	111.4
C11—N3—C8	107.4 (4)	C9—C10—H10A	111.4
C11—N3—Cd1	122.4 (4)	C11—C10—H10B	111.4
C8—N3—Cd1	113.9 (3)	C9—C10—H10B	111.4
C11—N3—H3B	103.7	H10A—C10—H10B	109.3
C8—N3—H3B	103.7	C8—C9—C10	104.6 (4)
Cd1—N3—H3B	103.7	C8—C9—H9A	110.8
C7—N2—C1	105.2 (3)	C10—C9—H9A	110.8
C7—N2—Cd1	113.3 (3)	C8—C9—H9B	110.8
C1—N2—Cd1	141.5 (3)	C10—C9—H9B	110.8
C7—N1—C6	107.9 (4)	H9A—C9—H9B	108.9
C7—N1—H1A	126.1	N3—C11—C10	107.5 (4)
C6—N1—H1A	126.1	N3—C11—H11A	110.2
C2—C3—C4	121.5 (5)	C10—C11—H11A	110.2
C2—C3—H3A	119.2	N3—C11—H11B	110.2
C4—C3—H3A	119.2	C10—C11—H11B	110.2
C4—C5—C6	117.0 (4)	H11A—C11—H11B	108.5
C4—C5—H5A	121.5	C2—C1—N2	131.3 (4)
C6—C5—H5A	121.5	C2—C1—C6	119.7 (4)
N1—C6—C5	132.5 (4)	N2—C1—C6	109.0 (4)

N2ⁱ—Cd1—O3—N4	88.5 (4)	C2—C3—C4—C5	0.3 (8)
N2—Cd1—O3—N4	−91.5 (4)	C1—N2—C7—N1	−1.5 (5)
N3ⁱ—Cd1—O3—N4	13.3 (4)	Cd1—N2—C7—N1	177.7 (3)
N3—Cd1—O3—N4	−166.7 (4)	C1—N2—C7—C8	175.2 (5)
O3ⁱ—Cd1—O3—N4	−136 (100)	Cd1—N2—C7—C8	−5.6 (6)
Cd1—O3—N4—O1	−0.9 (6)	C6—N1—C7—N2	1.2 (5)
Cd1—O3—N4—O2	−179.9 (3)	C6—N1—C7—C8	−175.7 (4)
N2ⁱ—Cd1—N3—C11	51.1 (5)	C4—C3—C2—C1	−0.6 (8)
N2—Cd1—N3—C11	−128.9 (5)	C11—N3—C8—C9	7.3 (6)
N3ⁱ—Cd1—N3—C11	137 (16)	Cd1—N3—C8—C9	−131.4 (4)
O3—Cd1—N3—C11	−38.0 (5)	C11—N3—C8—C7	132.7 (5)
O3ⁱ—Cd1—N3—C11	142.0 (5)	Cd1—N3—C8—C7	−6.0 (5)
N2ⁱ—Cd1—N3—C8	−177.1 (3)	N2—C7—C8—N3	8.1 (7)
N2—Cd1—N3—C8	2.9 (3)	N1—C7—C8—N3	−175.4 (4)
N3ⁱ—Cd1—N3—C8	−91 (16)	N2—C7—C8—C9	128.7 (5)
O3—Cd1—N3—C8	93.8 (4)	N1—C7—C8—C9	−54.9 (7)
O3ⁱ—Cd1—N3—C8	−86.2 (4)	N3—C8—C9—C10	−26.8 (6)
N2ⁱ—Cd1—N2—C7	61 (100)	C7—C8—C9—C10	−150.1 (5)
N3ⁱ—Cd1—N2—C7	−178.9 (3)	C11—C10—C9—C8	35.0 (7)
N3—Cd1—N2—C7	1.1 (3)	C8—N3—C11—C10	15.2 (7)
O3—Cd1—N2—C7	−84.3 (3)	Cd1—N3—C11—C10	149.7 (4)
O3ⁱ—Cd1—N2—C7	95.7 (3)	C9—C10—C11—N3	−31.1 (7)
N2ⁱ—Cd1—N2—C1	−120 (100)	C3—C2—C1—N2	179.7 (5)
N3ⁱ—Cd1—N2—C1	−0.1 (5)	C3—C2—C1—C6	0.5 (7)
N3—Cd1—N2—C1	179.9 (5)	C7—N2—C1—C2	−178.0 (5)
O3—Cd1—N2—C1	94.5 (5)	Cd1—N2—C1—C2	3.2 (8)
O3ⁱ—Cd1—N2—C1	−85.5 (5)	C7—N2—C1—C6	1.3 (5)
C7—N1—C6—C5	178.6 (5)	Cd1—N2—C1—C6	−177.6 (3)
C7—N1—C6—C1	−0.3 (5)	N1—C6—C1—C2	178.8 (4)
C4—C5—C6—N1	−178.7 (5)	C5—C6—C1—C2	−0.3 (7)
C4—C5—C6—C1	0.0 (7)	N1—C6—C1—N2	−0.6 (5)
C6—C5—C4—C3	−0.1 (7)	C5—C6—C1—N2	−179.6 (4)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.91	2.21	2.975 (7)	141
N1—H1A···O2ⁱⁱ	0.86	2.03	2.889 (5)	174

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

Experimental details

Crystal data
Chemical formula	[Cd(NO₃)₂(C₁₁H₁₂N₃)₂]
M_r	610.91
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.1487 (16), 9.1459 (18), 9.7439 (19)
α, β, γ (°)	111.67 (3), 112.32 (3), 93.80 (3)
V (Å³)	606.0 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.889, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	6172, 2692, 2258
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.114, 1.07
No. of reflections	2692
No. of parameters	169
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.45

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.91	2.21	2.975 (7)	140.7
N1—H1A···O2ⁱⁱ	0.86	2.03	2.889 (5)	173.9

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

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong.

References

Aminabhavi, T. M., Biradar, N. S. & Patil, S. B. (1986). Inorg. Chim. Acta, 125, 125–128. CrossRef CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ye, Q., Zhao, H., Qu, Z.-R., Ye, H.-Y. & Xiong, R.-G. (2008). Chem. Soc. Rev. 37, 84–100. Web of Science CrossRef PubMed Google Scholar