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

In the crystal struture of the title compound, C(10)H(10)N(2)O(2)·2H(2)O, the component species are linked to the water mol-ecules 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 = 226.23

Monoclinic,

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 ▶); 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 ▶).

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

C10H10N2O2·2H2O	F(000) = 480
Mr = 226.23	Dx = 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

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

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(Fo2) + (0.0354P)2 + 0.5171P] where P = (Fo2 + 2Fc2)/3
1971 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.19 e Å−3
6 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) ; (iii) .