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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2066.
Published online 2008 October 4. doi:  10.1107/S1600536808031346
PMCID: PMC2959715

3-(Benzimidazolium-2-yl)propionate dihydrate

Abstract

In the crystal struture of the title compound, C10H10N2O2·2H2O, the component species are linked to the water mol­ecules by N—H(...)O and O—H(...)O hydrogen bonds to form a three-dimensional network structure.

Related literature

For general background, see: Day & Arnold (2000 [triangle]); Day et al. (2002 [triangle]); Freeman et al. (1981 [triangle]); Kim et al. (2000 [triangle]). For related structure, see: Ge et al. (2007 [triangle]).

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Object name is e-64-o2066-scheme1.jpg

Experimental

Crystal data

  • C10H10N2O2·2H2O
  • M r = 226.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2066-efi1.jpg
  • a = 18.444 (3) Å
  • b = 4.9730 (8) Å
  • c = 11.9097 (19) Å
  • β = 94.530 (5)°
  • V = 1089.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 273 (2) K
  • 0.29 × 0.26 × 0.20 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 7787 measured reflections
  • 2002 independent reflections
  • 1394 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.113
  • S = 1.08
  • 1971 reflections
  • 161 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031346/ng2490sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031346/ng2490Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge the Natural Science Foundation of China (grant No. 20767001), the International Collaborative Project of Guizhou Province, the Governor Foundation of Guizhou Province and the Natural Science Youth Foundation of Guizhou University (grant No. 2007-005) for financial support.

supplementary crystallographic information

Comment

As part of our ongoing investigation on benzimidazole compounds, we present a compound containing multiple functional groups that can develop strong intermolecular interactions with cucurbit[n]urils (CB[n]) (Freeman et al., 1981; Day & Arnold, 2000; Day et al., 2002; Kim et al., 2000; Ge et al., 2007).

The crystal structure of the title compound (Fig. 1) consists of a 3-(1H-benzo[d]imidazol-2-yl) propanoic acid organic molecule and two lattice water molecules. the dihedral angle between the benzene ring (C1,C2,C3,C4,C5,C6) and the imidazole ring (C5,C6,C9,N2,C7,N1) is 0.61 (13)°. The C7—C8—C9—C10 torsion angle is -66.3 (3)°. The title compound forms intermolecular H bonds whereas the protonated N1 and N2 atoms act as hydrogen-bond donors and the O1 and O2 atoms act as hydrogen-bond acceptors, the O—H···O hydrogen bonds are also observed between the water molecules O2W and O1W (Table 1). these contacts and the cross-linking interactions stabilize the crystal packing.

Experimental

The propionic anhydride (13 g, 0.1 mol) was dissolved in hot water (100 ml) with stirring, and a warm solution of 1,2-diaminobenzene(10.8 g, 0.1 mol) in 1,4-dioxane (100 ml) was added, following by the addition of ployphosphoric acid (50 ml) as catalyst. The mixture was refluxed for 8 h and then cooled, the solution was filtered and the filtrate was set aside for three weeks to obtain colorless crystals.

Refinement

Water H atoms were located in a difference Fourier map and refined as riding in their as-found positions relative to O atoms with Uiso(H) = 1.2Ueq(O). All other H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.97 Å, N—H = 0.86 Å, and Uiso(H) = 1.2–1.5 Ueq(C,N).

Figures

Fig. 1.
The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C10H10N2O2·2H2OF(000) = 480
Mr = 226.23Dx = 1.380 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2002 reflections
a = 18.444 (3) Åθ = 1.1–25.4°
b = 4.9730 (8) ŵ = 0.11 mm1
c = 11.9097 (19) ÅT = 273 K
β = 94.530 (5)°Prism, colourless
V = 1089.0 (3) Å30.29 × 0.26 × 0.20 mm
Z = 4

Data collection

Bruker CCD area-detector diffractometer1394 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
graphiteθmax = 25.4°, θmin = 1.1°
[var phi] and ω scansh = −21→19
7787 measured reflectionsk = −5→4
2002 independent reflectionsl = −13→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0354P)2 + 0.5171P] where P = (Fo2 + 2Fc2)/3
1971 reflections(Δ/σ)max < 0.001
161 parametersΔρmax = 0.19 e Å3
6 restraintsΔρmin = −0.23 e Å3

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
O10.24941 (9)0.3021 (3)0.56604 (13)0.0306 (5)
O20.31408 (9)0.3485 (3)0.41718 (12)0.0285 (4)
O1W0.45721 (11)0.3587 (4)0.36594 (15)0.0360 (5)
O2W0.52898 (12)−0.1307 (4)0.37002 (17)0.0398 (5)
N10.22255 (10)0.8913 (4)0.70511 (15)0.0249 (5)
H1N0.22961.00210.65160.030*
N20.23986 (10)0.5625 (4)0.82389 (15)0.0241 (5)
H2N0.25950.42660.85910.029*
C10.12302 (14)0.6171 (5)0.92071 (19)0.0290 (6)
H1A0.13030.47750.97230.035*
C20.06132 (14)0.7751 (5)0.9168 (2)0.0331 (7)
H2A0.02640.74170.96730.040*
C30.04988 (14)0.9848 (5)0.8385 (2)0.0334 (7)
H3A0.00741.08580.83800.040*
C40.09993 (13)1.0447 (5)0.7624 (2)0.0300 (6)
H4A0.09241.18380.71070.036*
C50.16226 (13)0.8870 (5)0.76689 (18)0.0237 (6)
C60.17353 (13)0.6765 (5)0.84417 (18)0.0238 (6)
C70.26826 (13)0.6960 (5)0.74162 (18)0.0234 (6)
C80.34047 (13)0.6448 (5)0.69974 (18)0.0264 (6)
H8A0.35820.47240.72850.032*
H8B0.37410.78160.72990.032*
C90.34097 (13)0.6433 (5)0.57180 (18)0.0252 (6)
H9A0.32070.81150.54250.030*
H9B0.39090.63340.55210.030*
C100.29840 (13)0.4120 (5)0.51556 (18)0.0227 (6)
H1W10.4133 (12)0.352 (7)0.386 (3)0.084 (13)*
H1W20.4755 (16)0.208 (4)0.384 (3)0.059 (11)*
H2W10.5341 (16)−0.149 (6)0.3009 (16)0.053 (9)*
H2W20.5073 (19)−0.268 (5)0.387 (3)0.089 (14)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0340 (10)0.0248 (10)0.0334 (9)−0.0060 (8)0.0054 (8)0.0027 (8)
O20.0334 (10)0.0268 (10)0.0255 (8)−0.0038 (8)0.0042 (8)−0.0056 (7)
O1W0.0374 (13)0.0303 (12)0.0416 (11)−0.0013 (10)0.0106 (10)−0.0001 (9)
O2W0.0486 (13)0.0315 (12)0.0399 (11)−0.0038 (11)0.0079 (10)−0.0010 (10)
N10.0311 (12)0.0209 (12)0.0230 (9)−0.0003 (10)0.0032 (9)0.0034 (9)
N20.0290 (12)0.0205 (12)0.0225 (9)0.0022 (10)0.0013 (9)0.0013 (8)
C10.0336 (15)0.0257 (15)0.0281 (12)−0.0059 (13)0.0043 (11)−0.0011 (11)
C20.0315 (15)0.0340 (16)0.0348 (14)−0.0053 (13)0.0090 (12)−0.0058 (12)
C30.0292 (15)0.0272 (15)0.0438 (15)0.0027 (13)0.0035 (13)−0.0062 (13)
C40.0309 (15)0.0231 (15)0.0354 (13)0.0009 (12)−0.0006 (12)−0.0010 (11)
C50.0267 (14)0.0194 (14)0.0248 (11)−0.0044 (11)0.0016 (11)−0.0032 (10)
C60.0268 (14)0.0198 (13)0.0248 (12)−0.0005 (11)0.0010 (11)−0.0029 (10)
C70.0289 (14)0.0202 (13)0.0206 (11)−0.0035 (12)−0.0004 (10)−0.0045 (10)
C80.0240 (14)0.0271 (15)0.0279 (12)−0.0009 (12)0.0006 (11)−0.0011 (11)
C90.0289 (14)0.0208 (14)0.0264 (12)−0.0028 (12)0.0049 (11)0.0005 (11)
C100.0257 (14)0.0167 (13)0.0256 (12)0.0048 (11)0.0012 (11)0.0050 (10)

Geometric parameters (Å, °)

O1—C101.250 (3)C2—C31.404 (4)
O2—C101.269 (3)C2—H2A0.9300
O1W—H1W10.863 (18)C3—C41.376 (3)
O1W—H1W20.845 (18)C3—H3A0.9300
O2W—H2W10.841 (17)C4—C51.389 (3)
O2W—H2W20.823 (18)C4—H4A0.9300
N1—C71.336 (3)C5—C61.399 (3)
N1—C51.381 (3)C7—C81.481 (3)
N1—H1N0.8600C8—C91.525 (3)
N2—C71.325 (3)C8—H8A0.9700
N2—C61.387 (3)C8—H8B0.9700
N2—H2N0.8600C9—C101.518 (3)
C1—C21.380 (3)C9—H9A0.9700
C1—C61.386 (3)C9—H9B0.9700
C1—H1A0.9300
H1W1—O1W—H1W2105 (3)C4—C5—C6121.8 (2)
H2W1—O2W—H2W2104 (3)C1—C6—N2132.5 (2)
C7—N1—C5109.22 (19)C1—C6—C5121.3 (2)
C7—N1—H1N125.4N2—C6—C5106.2 (2)
C5—N1—H1N125.4N2—C7—N1109.2 (2)
C7—N2—C6109.2 (2)N2—C7—C8125.6 (2)
C7—N2—H2N125.4N1—C7—C8125.2 (2)
C6—N2—H2N125.4C7—C8—C9114.5 (2)
C2—C1—C6116.9 (2)C7—C8—H8A108.6
C2—C1—H1A121.6C9—C8—H8A108.6
C6—C1—H1A121.6C7—C8—H8B108.6
C1—C2—C3121.7 (2)C9—C8—H8B108.6
C1—C2—H2A119.2H8A—C8—H8B107.6
C3—C2—H2A119.2C10—C9—C8113.63 (19)
C4—C3—C2121.6 (2)C10—C9—H9A108.8
C4—C3—H3A119.2C8—C9—H9A108.8
C2—C3—H3A119.2C10—C9—H9B108.8
C3—C4—C5116.7 (2)C8—C9—H9B108.8
C3—C4—H4A121.7H9A—C9—H9B107.7
C5—C4—H4A121.7O1—C10—O2124.2 (2)
N1—C5—C4132.0 (2)O1—C10—C9119.2 (2)
N1—C5—C6106.1 (2)O2—C10—C9116.6 (2)
C6—C1—C2—C30.5 (4)C4—C5—C6—C1−0.5 (3)
C1—C2—C3—C4−0.6 (4)N1—C5—C6—N2−0.7 (2)
C2—C3—C4—C50.1 (4)C4—C5—C6—N2179.2 (2)
C7—N1—C5—C4−179.9 (2)C6—N2—C7—N1−1.2 (3)
C7—N1—C5—C60.0 (2)C6—N2—C7—C8176.5 (2)
C3—C4—C5—N1−179.6 (2)C5—N1—C7—N20.7 (2)
C3—C4—C5—C60.4 (3)C5—N1—C7—C8−177.0 (2)
C2—C1—C6—N2−179.6 (2)N2—C7—C8—C9135.7 (2)
C2—C1—C6—C50.1 (3)N1—C7—C8—C9−47.0 (3)
C7—N2—C6—C1−179.1 (2)C7—C8—C9—C10−66.3 (3)
C7—N2—C6—C51.2 (2)C8—C9—C10—O123.1 (3)
N1—C5—C6—C1179.5 (2)C8—C9—C10—O2−159.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.861.862.700 (2)166
N2—H2N···O2ii0.861.802.654 (3)170
O2W—H2W1···O1Wiii0.84 (2)2.01 (2)2.842 (3)172 (3)

Symmetry codes: (i) x, y+1, z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2490).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Day, A. I. & Arnold, A. P. (2000). Int. Patent WO/2000/068232.
  • Day, A. I., Blanch, R. J., Arnold, A. P., Lorenzo, S., Lewis, G. R. & Dance, I. (2002). Angew. Chem. Int. Ed.41, 275–277. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Freeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc.103, 7367–7368.
  • Ge, J. Y., Xue, S. F., Zhu, Q. J., Tao, Z. & Zhang, J., X. (2007). J. Incl. Phenom. Macro.58, 63–69.
  • Kim, J., Jung, I.-S., Kim, S.-Y., Lee, E., Kang, J.-K., Sakamoto, S., Yamaguchi, K. & Kim, K. (2000). J. Am. Chem. Soc.122, 540–541.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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