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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1017.
Published online 2008 July 9. doi:  10.1107/S1600536808006454
PMCID: PMC2961940

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

Abstract

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 [triangle]); Ye et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1017-scheme1.jpg

Experimental

Crystal data

  • [Cd(NO3)2(C11H12N3)2]
  • M r = 610.91
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1017-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.114
  • S = 1.07
  • 2692 reflections
  • 169 parameters
  • H-atom parameters constrained
  • Δρmax = 0.69 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Positional parameters of all the H atoms bonded to C or N atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with Uiso(H) = 1.2Ueq(C or N).

Figures

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.

Crystal data

[Cd(NO3)2(C11H12N3)2]Z = 1
Mr = 610.91F000 = 310
Triclinic, P1Dx = 1.674 Mg m3
Hall symbol: -P1Mo Kα radiation λ = 0.71073 Å
a = 8.1487 (16) ÅCell parameters from 2061 reflections
b = 9.1459 (18) Åθ = 3.3–27.5º
c = 9.7439 (19) ŵ = 0.96 mm1
α = 111.67 (3)ºT = 293 (2) K
β = 112.32 (3)ºPrism, colorless
γ = 93.80 (3)º0.12 × 0.10 × 0.06 mm
V = 606.0 (2) Å3

Data collection

Rigaku Mercury2 diffractometer2692 independent reflections
Radiation source: fine-focus sealed tube2258 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.057
Detector resolution: 13.6612 pixels mm-1θmax = 27.3º
T = 293(2) Kθmin = 3.3º
CCD profile fitting scansh = −10→10
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −11→11
Tmin = 0.889, Tmax = 0.944l = −12→12
6172 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.114  w = 1/[σ2(Fo2) + (0.0464P)2 + 0.245P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2692 reflectionsΔρmax = 0.69 e Å3
169 parametersΔρmin = −0.44 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Cd10.00000.50000.00000.03774 (18)
O10.1413 (6)0.8668 (6)−0.0027 (6)0.0919 (14)
O20.2395 (5)0.7989 (5)−0.1864 (5)0.0701 (11)
O30.1342 (6)0.6144 (5)−0.1353 (5)0.0730 (11)
N40.1714 (5)0.7596 (6)−0.1065 (5)0.0503 (10)
N30.0853 (6)0.2624 (5)−0.1240 (5)0.0585 (11)
H3B0.00500.1820−0.13220.070*
N20.2902 (4)0.5267 (4)0.1908 (4)0.0376 (8)
N10.5347 (5)0.4236 (5)0.2503 (5)0.0470 (9)
H1A0.60400.35770.23840.056*
C30.5789 (7)0.8578 (6)0.6093 (6)0.0557 (13)
H3A0.58180.95640.68690.067*
C50.7348 (6)0.6476 (6)0.5341 (5)0.0453 (11)
H5A0.83650.60410.55760.054*
C60.5793 (6)0.5690 (5)0.3855 (5)0.0376 (9)
C40.7314 (7)0.7920 (6)0.6443 (6)0.0522 (12)
H4A0.83310.84760.74480.063*
C70.3627 (6)0.4036 (6)0.1402 (5)0.0444 (11)
C20.4236 (6)0.7797 (6)0.4619 (6)0.0487 (11)
H2A0.32210.82380.43980.058*
C80.2668 (7)0.2502 (6)−0.0174 (6)0.0524 (12)
H8A0.24720.16030.01080.063*
C100.2213 (6)0.1190 (6)−0.2943 (6)0.0543 (13)
H10A0.26350.1286−0.37190.065*
H10B0.18040.0053−0.32290.065*
C90.3685 (7)0.2075 (8)−0.1197 (6)0.0741 (18)
H9A0.44720.1382−0.09090.089*
H9B0.44240.3042−0.10550.089*
C110.0726 (9)0.2075 (9)−0.2880 (6)0.085 (2)
H11A0.08860.2992−0.31310.102*
H11B−0.04630.1356−0.36780.102*
C10.4241 (6)0.6332 (5)0.3478 (5)0.0360 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.0274 (3)0.0437 (3)0.0305 (3)0.00864 (18)0.00878 (18)0.00795 (19)
O10.084 (3)0.095 (3)0.080 (3)0.020 (3)0.050 (3)0.005 (3)
O20.073 (3)0.080 (3)0.092 (3)0.040 (2)0.048 (2)0.057 (2)
O30.074 (3)0.077 (3)0.092 (3)0.021 (2)0.050 (2)0.045 (2)
N40.032 (2)0.071 (3)0.046 (2)0.022 (2)0.0137 (18)0.024 (2)
N30.043 (2)0.060 (3)0.048 (2)0.012 (2)0.016 (2)0.003 (2)
N20.0310 (19)0.044 (2)0.0297 (17)0.0114 (15)0.0110 (15)0.0098 (15)
N10.039 (2)0.060 (3)0.044 (2)0.0233 (18)0.0198 (18)0.0208 (19)
C30.054 (3)0.051 (3)0.040 (3)0.009 (2)0.011 (2)0.008 (2)
C50.034 (2)0.060 (3)0.041 (2)0.015 (2)0.010 (2)0.027 (2)
C60.036 (2)0.044 (2)0.032 (2)0.0081 (18)0.0126 (19)0.0183 (19)
C40.044 (3)0.060 (3)0.034 (2)0.005 (2)0.004 (2)0.016 (2)
C70.043 (3)0.054 (3)0.035 (2)0.017 (2)0.017 (2)0.018 (2)
C20.039 (3)0.054 (3)0.044 (3)0.019 (2)0.014 (2)0.015 (2)
C80.050 (3)0.055 (3)0.044 (3)0.020 (2)0.017 (2)0.015 (2)
C100.046 (3)0.065 (3)0.036 (3)0.017 (2)0.016 (2)0.007 (2)
C90.044 (3)0.108 (5)0.038 (3)0.023 (3)0.013 (2)0.002 (3)
C110.081 (4)0.113 (5)0.034 (3)0.062 (4)0.016 (3)0.008 (3)
C10.031 (2)0.044 (2)0.033 (2)0.0113 (18)0.0107 (18)0.0181 (19)

Geometric parameters (Å, °)

Cd1—N2i2.314 (3)C3—H3A0.9300
Cd1—N22.314 (3)C5—C41.370 (7)
Cd1—N3i2.359 (4)C5—C61.391 (6)
Cd1—N32.359 (4)C5—H5A0.9300
Cd1—O32.448 (4)C6—C11.409 (6)
Cd1—O3i2.448 (4)C4—H4A0.9300
O1—N41.238 (5)C7—C81.513 (7)
O2—N41.245 (5)C2—C11.391 (6)
O3—N41.241 (5)C2—H2A0.9300
N3—C111.447 (7)C8—C91.488 (7)
N3—C81.490 (6)C8—H8A0.9800
N3—H3B0.9100C10—C111.509 (7)
N2—C71.327 (6)C10—C91.514 (7)
N2—C11.403 (5)C10—H10A0.9700
N1—C71.352 (6)C10—H10B0.9700
N1—C61.384 (6)C9—H9A0.9700
N1—H1A0.8600C9—H9B0.9700
C3—C21.385 (7)C11—H11A0.9700
C3—C41.397 (7)C11—H11B0.9700
N2i—Cd1—N2180.00 (18)N1—C6—C1105.2 (4)
N2i—Cd1—N3i75.24 (13)C5—C6—C1122.3 (4)
N2—Cd1—N3i104.76 (13)C5—C4—C3121.6 (4)
N2i—Cd1—N3104.76 (13)C5—C4—H4A119.2
N2—Cd1—N375.24 (13)C3—C4—H4A119.2
N3i—Cd1—N3180.0N2—C7—N1112.7 (4)
N2i—Cd1—O390.22 (13)N2—C7—C8125.9 (4)
N2—Cd1—O389.78 (13)N1—C7—C8121.4 (4)
N3i—Cd1—O394.44 (15)C3—C2—C1117.9 (4)
N3—Cd1—O385.56 (15)C3—C2—H2A121.1
N2i—Cd1—O3i89.78 (13)C1—C2—H2A121.1
N2—Cd1—O3i90.22 (13)N3—C8—C9106.3 (4)
N3i—Cd1—O3i85.56 (15)N3—C8—C7111.2 (4)
N3—Cd1—O3i94.44 (15)C9—C8—C7114.6 (5)
O3—Cd1—O3i180.0N3—C8—H8A108.2
N4—O3—Cd1126.5 (3)C9—C8—H8A108.2
O1—N4—O3122.5 (5)C7—C8—H8A108.2
O1—N4—O2118.7 (5)C11—C10—C9101.8 (4)
O3—N4—O2118.9 (4)C11—C10—H10A111.4
C11—N3—C8107.4 (4)C9—C10—H10A111.4
C11—N3—Cd1122.4 (4)C11—C10—H10B111.4
C8—N3—Cd1113.9 (3)C9—C10—H10B111.4
C11—N3—H3B103.7H10A—C10—H10B109.3
C8—N3—H3B103.7C8—C9—C10104.6 (4)
Cd1—N3—H3B103.7C8—C9—H9A110.8
C7—N2—C1105.2 (3)C10—C9—H9A110.8
C7—N2—Cd1113.3 (3)C8—C9—H9B110.8
C1—N2—Cd1141.5 (3)C10—C9—H9B110.8
C7—N1—C6107.9 (4)H9A—C9—H9B108.9
C7—N1—H1A126.1N3—C11—C10107.5 (4)
C6—N1—H1A126.1N3—C11—H11A110.2
C2—C3—C4121.5 (5)C10—C11—H11A110.2
C2—C3—H3A119.2N3—C11—H11B110.2
C4—C3—H3A119.2C10—C11—H11B110.2
C4—C5—C6117.0 (4)H11A—C11—H11B108.5
C4—C5—H5A121.5C2—C1—N2131.3 (4)
C6—C5—H5A121.5C2—C1—C6119.7 (4)
N1—C6—C5132.5 (4)N2—C1—C6109.0 (4)
N2i—Cd1—O3—N488.5 (4)C2—C3—C4—C50.3 (8)
N2—Cd1—O3—N4−91.5 (4)C1—N2—C7—N1−1.5 (5)
N3i—Cd1—O3—N413.3 (4)Cd1—N2—C7—N1177.7 (3)
N3—Cd1—O3—N4−166.7 (4)C1—N2—C7—C8175.2 (5)
O3i—Cd1—O3—N4−136 (100)Cd1—N2—C7—C8−5.6 (6)
Cd1—O3—N4—O1−0.9 (6)C6—N1—C7—N21.2 (5)
Cd1—O3—N4—O2−179.9 (3)C6—N1—C7—C8−175.7 (4)
N2i—Cd1—N3—C1151.1 (5)C4—C3—C2—C1−0.6 (8)
N2—Cd1—N3—C11−128.9 (5)C11—N3—C8—C97.3 (6)
N3i—Cd1—N3—C11137 (16)Cd1—N3—C8—C9−131.4 (4)
O3—Cd1—N3—C11−38.0 (5)C11—N3—C8—C7132.7 (5)
O3i—Cd1—N3—C11142.0 (5)Cd1—N3—C8—C7−6.0 (5)
N2i—Cd1—N3—C8−177.1 (3)N2—C7—C8—N38.1 (7)
N2—Cd1—N3—C82.9 (3)N1—C7—C8—N3−175.4 (4)
N3i—Cd1—N3—C8−91 (16)N2—C7—C8—C9128.7 (5)
O3—Cd1—N3—C893.8 (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—C761 (100)C7—C8—C9—C10−150.1 (5)
N3i—Cd1—N2—C7−178.9 (3)C11—C10—C9—C835.0 (7)
N3—Cd1—N2—C71.1 (3)C8—N3—C11—C1015.2 (7)
O3—Cd1—N2—C7−84.3 (3)Cd1—N3—C11—C10149.7 (4)
O3i—Cd1—N2—C795.7 (3)C9—C10—C11—N3−31.1 (7)
N2i—Cd1—N2—C1−120 (100)C3—C2—C1—N2179.7 (5)
N3i—Cd1—N2—C1−0.1 (5)C3—C2—C1—C60.5 (7)
N3—Cd1—N2—C1179.9 (5)C7—N2—C1—C2−178.0 (5)
O3—Cd1—N2—C194.5 (5)Cd1—N2—C1—C23.2 (8)
O3i—Cd1—N2—C1−85.5 (5)C7—N2—C1—C61.3 (5)
C7—N1—C6—C5178.6 (5)Cd1—N2—C1—C6−177.6 (3)
C7—N1—C6—C1−0.3 (5)N1—C6—C1—C2178.8 (4)
C4—C5—C6—N1−178.7 (5)C5—C6—C1—C2−0.3 (7)
C4—C5—C6—C10.0 (7)N1—C6—C1—N2−0.6 (5)
C6—C5—C4—C3−0.1 (7)C5—C6—C1—N2−179.6 (4)

Symmetry codes: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3B···O1i0.912.212.975 (7)141
N1—H1A···O2ii0.862.032.889 (5)174

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2315).

References

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

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