3-(Benzimidazolium-2-yl)propionate dihydrate

Xiao, X.; Zhang, Y.-Q.; Xue, S.-F.; Tao, Z.

doi:10.1107/S1600536808031346

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2066

doi:10.1107/S1600536808031346

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3-(Benzimidazolium-2-yl)propionate dihydrate

Xin Xiao,^a Yun-Qiang Zhang,^a Sai-Feng Xue ^a and Zhu Tao ^b ^*

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and ^bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: gyhxxiaoxin@163.com

(Received 4 September 2008; accepted 27 September 2008; online 4 October 2008)

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 ); Day et al. (2002 ); Freeman et al. (1981 ); Kim et al. (2000 ). For related structure, see: Ge et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₀N₂O₂·2H₂O
M_r = 226.23
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.113
S = 1.08
1971 reflections
161 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	1.86	2.700 (2)	166
N2—H2N⋯O2ⁱⁱ	0.86	1.80	2.654 (3)	170
O2W—H2W1⋯O1Wⁱⁱⁱ	0.841 (17)	2.007 (18)	2.842 (3)	172 (3)
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

For general background, see: Day & Arnold (2000); Day et al. (2002); Freeman et al. (1981); Kim et al. (2000); Ge et al. (2007). [From the Section Editors: It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···." etc. Please revise this section as indicated.]

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

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

3-(Benzimidazolium-2-yl)propionate dihydrate top

Crystal data top

C₁₀H₁₀N₂O₂·2H₂O	F(000) = 480
M_r = 226.23	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2002 reflections
a = 18.444 (3) Å	θ = 1.1–25.4°
b = 4.9730 (8) Å	µ = 0.11 mm⁻¹
c = 11.9097 (19) Å	T = 273 K
β = 94.530 (5)°	Prism, colourless
V = 1089.0 (3) Å³	0.29 × 0.26 × 0.20 mm
Z = 4

Data collection top

Bruker CCD area-detector diffractometer	1394 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.066
Graphite monochromator	θ_max = 25.4°, θ_min = 1.1°
ϕ and ω scans	h = −21→19
7787 measured reflections	k = −5→4
2002 independent reflections	l = −13→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0354P)² + 0.5171P] where P = (F_o² + 2F_c²)/3
1971 reflections	(Δ/σ)_max < 0.001
161 parameters	Δρ_max = 0.19 e Å⁻³
6 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₁₀N₂O₂·2H₂O	V = 1089.0 (3) Å³
M_r = 226.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.444 (3) Å	µ = 0.11 mm⁻¹
b = 4.9730 (8) Å	T = 273 K
c = 11.9097 (19) Å	0.29 × 0.26 × 0.20 mm
β = 94.530 (5)°

Data collection top

Bruker CCD area-detector diffractometer	1394 reflections with I > 2σ(I)
7787 measured reflections	R_int = 0.066
2002 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	6 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.19 e Å⁻³
1971 reflections	Δρ_min = −0.23 e Å⁻³
161 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
O1	0.24941 (9)	0.3021 (3)	0.56604 (13)	0.0306 (5)
O2	0.31408 (9)	0.3485 (3)	0.41718 (12)	0.0285 (4)
O1W	0.45721 (11)	0.3587 (4)	0.36594 (15)	0.0360 (5)
O2W	0.52898 (12)	−0.1307 (4)	0.37002 (17)	0.0398 (5)
N1	0.22255 (10)	0.8913 (4)	0.70511 (15)	0.0249 (5)
H1N	0.2296	1.0021	0.6516	0.030*
N2	0.23986 (10)	0.5625 (4)	0.82389 (15)	0.0241 (5)
H2N	0.2595	0.4266	0.8591	0.029*
C1	0.12302 (14)	0.6171 (5)	0.92071 (19)	0.0290 (6)
H1A	0.1303	0.4775	0.9723	0.035*
C2	0.06132 (14)	0.7751 (5)	0.9168 (2)	0.0331 (7)
H2A	0.0264	0.7417	0.9673	0.040*
C3	0.04988 (14)	0.9848 (5)	0.8385 (2)	0.0334 (7)
H3A	0.0074	1.0858	0.8380	0.040*
C4	0.09993 (13)	1.0447 (5)	0.7624 (2)	0.0300 (6)
H4A	0.0924	1.1838	0.7107	0.036*
C5	0.16226 (13)	0.8870 (5)	0.76689 (18)	0.0237 (6)
C6	0.17353 (13)	0.6765 (5)	0.84417 (18)	0.0238 (6)
C7	0.26826 (13)	0.6960 (5)	0.74162 (18)	0.0234 (6)
C8	0.34047 (13)	0.6448 (5)	0.69974 (18)	0.0264 (6)
H8A	0.3582	0.4724	0.7285	0.032*
H8B	0.3741	0.7816	0.7299	0.032*
C9	0.34097 (13)	0.6433 (5)	0.57180 (18)	0.0252 (6)
H9A	0.3207	0.8115	0.5425	0.030*
H9B	0.3909	0.6334	0.5521	0.030*
C10	0.29840 (13)	0.4120 (5)	0.51556 (18)	0.0227 (6)
H1W1	0.4133 (12)	0.352 (7)	0.386 (3)	0.084 (13)*
H1W2	0.4755 (16)	0.208 (4)	0.384 (3)	0.059 (11)*
H2W1	0.5341 (16)	−0.149 (6)	0.3009 (16)	0.053 (9)*
H2W2	0.5073 (19)	−0.268 (5)	0.387 (3)	0.089 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0340 (10)	0.0248 (10)	0.0334 (9)	−0.0060 (8)	0.0054 (8)	0.0027 (8)
O2	0.0334 (10)	0.0268 (10)	0.0255 (8)	−0.0038 (8)	0.0042 (8)	−0.0056 (7)
O1W	0.0374 (13)	0.0303 (12)	0.0416 (11)	−0.0013 (10)	0.0106 (10)	−0.0001 (9)
O2W	0.0486 (13)	0.0315 (12)	0.0399 (11)	−0.0038 (11)	0.0079 (10)	−0.0010 (10)
N1	0.0311 (12)	0.0209 (12)	0.0230 (9)	−0.0003 (10)	0.0032 (9)	0.0034 (9)
N2	0.0290 (12)	0.0205 (12)	0.0225 (9)	0.0022 (10)	0.0013 (9)	0.0013 (8)
C1	0.0336 (15)	0.0257 (15)	0.0281 (12)	−0.0059 (13)	0.0043 (11)	−0.0011 (11)
C2	0.0315 (15)	0.0340 (16)	0.0348 (14)	−0.0053 (13)	0.0090 (12)	−0.0058 (12)
C3	0.0292 (15)	0.0272 (15)	0.0438 (15)	0.0027 (13)	0.0035 (13)	−0.0062 (13)
C4	0.0309 (15)	0.0231 (15)	0.0354 (13)	0.0009 (12)	−0.0006 (12)	−0.0010 (11)
C5	0.0267 (14)	0.0194 (14)	0.0248 (11)	−0.0044 (11)	0.0016 (11)	−0.0032 (10)
C6	0.0268 (14)	0.0198 (13)	0.0248 (12)	−0.0005 (11)	0.0010 (11)	−0.0029 (10)
C7	0.0289 (14)	0.0202 (13)	0.0206 (11)	−0.0035 (12)	−0.0004 (10)	−0.0045 (10)
C8	0.0240 (14)	0.0271 (15)	0.0279 (12)	−0.0009 (12)	0.0006 (11)	−0.0011 (11)
C9	0.0289 (14)	0.0208 (14)	0.0264 (12)	−0.0028 (12)	0.0049 (11)	0.0005 (11)
C10	0.0257 (14)	0.0167 (13)	0.0256 (12)	0.0048 (11)	0.0012 (11)	0.0050 (10)

Geometric parameters (Å, º) top

O1—C10	1.250 (3)	C2—C3	1.404 (4)
O2—C10	1.269 (3)	C2—H2A	0.9300
O1W—H1W1	0.863 (18)	C3—C4	1.376 (3)
O1W—H1W2	0.845 (18)	C3—H3A	0.9300
O2W—H2W1	0.841 (17)	C4—C5	1.389 (3)
O2W—H2W2	0.823 (18)	C4—H4A	0.9300
N1—C7	1.336 (3)	C5—C6	1.399 (3)
N1—C5	1.381 (3)	C7—C8	1.481 (3)
N1—H1N	0.8600	C8—C9	1.525 (3)
N2—C7	1.325 (3)	C8—H8A	0.9700
N2—C6	1.387 (3)	C8—H8B	0.9700
N2—H2N	0.8600	C9—C10	1.518 (3)
C1—C2	1.380 (3)	C9—H9A	0.9700
C1—C6	1.386 (3)	C9—H9B	0.9700
C1—H1A	0.9300

H1W1—O1W—H1W2	105 (3)	C4—C5—C6	121.8 (2)
H2W1—O2W—H2W2	104 (3)	C1—C6—N2	132.5 (2)
C7—N1—C5	109.22 (19)	C1—C6—C5	121.3 (2)
C7—N1—H1N	125.4	N2—C6—C5	106.2 (2)
C5—N1—H1N	125.4	N2—C7—N1	109.2 (2)
C7—N2—C6	109.2 (2)	N2—C7—C8	125.6 (2)
C7—N2—H2N	125.4	N1—C7—C8	125.2 (2)
C6—N2—H2N	125.4	C7—C8—C9	114.5 (2)
C2—C1—C6	116.9 (2)	C7—C8—H8A	108.6
C2—C1—H1A	121.6	C9—C8—H8A	108.6
C6—C1—H1A	121.6	C7—C8—H8B	108.6
C1—C2—C3	121.7 (2)	C9—C8—H8B	108.6
C1—C2—H2A	119.2	H8A—C8—H8B	107.6
C3—C2—H2A	119.2	C10—C9—C8	113.63 (19)
C4—C3—C2	121.6 (2)	C10—C9—H9A	108.8
C4—C3—H3A	119.2	C8—C9—H9A	108.8
C2—C3—H3A	119.2	C10—C9—H9B	108.8
C3—C4—C5	116.7 (2)	C8—C9—H9B	108.8
C3—C4—H4A	121.7	H9A—C9—H9B	107.7
C5—C4—H4A	121.7	O1—C10—O2	124.2 (2)
N1—C5—C4	132.0 (2)	O1—C10—C9	119.2 (2)
N1—C5—C6	106.1 (2)	O2—C10—C9	116.6 (2)

C6—C1—C2—C3	0.5 (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—C5	0.1 (4)	C4—C5—C6—N2	179.2 (2)
C7—N1—C5—C4	−179.9 (2)	C6—N2—C7—N1	−1.2 (3)
C7—N1—C5—C6	0.0 (2)	C6—N2—C7—C8	176.5 (2)
C3—C4—C5—N1	−179.6 (2)	C5—N1—C7—N2	0.7 (2)
C3—C4—C5—C6	0.4 (3)	C5—N1—C7—C8	−177.0 (2)
C2—C1—C6—N2	−179.6 (2)	N2—C7—C8—C9	135.7 (2)
C2—C1—C6—C5	0.1 (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—C5	1.2 (2)	C8—C9—C10—O1	23.1 (3)
N1—C5—C6—C1	179.5 (2)	C8—C9—C10—O2	−159.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	1.86	2.700 (2)	166
N2—H2N···O2ⁱⁱ	0.86	1.80	2.654 (3)	170
O2W—H2W1···O1Wⁱⁱⁱ	0.84 (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.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂O₂·2H₂O
M_r	226.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	18.444 (3), 4.9730 (8), 11.9097 (19)
β (°)	94.530 (5)
V (Å³)	1089.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.29 × 0.26 × 0.20

Data collection
Diffractometer	Bruker CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7787, 2002, 1394
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.113, 1.08
No. of reflections	1971
No. of parameters	161
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	1.86	2.700 (2)	165.5
N2—H2N···O2ⁱⁱ	0.86	1.80	2.654 (3)	169.6
O2W—H2W1···O1Wⁱⁱⁱ	0.841 (17)	2.007 (18)	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.

Acknowledgements

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.

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