In the crystal struture of the title compound, C
10H
10N
2O
2·2H
2O, 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.
Supporting information
CCDC reference: 709312
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.113
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels .......... 4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
H2 O
Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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.
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).
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).
3-(Benzimidazolium-2-yl)propionate dihydrate
top
Crystal data top
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 | |
Data collection top
Bruker CCD area-detector diffractometer | 1394 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | 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 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(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 |
Crystal data top
C10H10N2O2·2H2O | V = 1089.0 (3) Å3 |
Mr = 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 | Rint = 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 | Δρmax = 0.19 e Å−3 |
1971 reflections | Δρmin = −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 | 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)* | |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.19, −0.23 |
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. |
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.