organic compounds
Benzimidazolium 3,5-dicarboxybenzoate trihydrate
aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecule, Tianjin Normal University, Tianjin 300387, People's Republic of China
*Correspondence e-mail: luckyms@126.com
Cocrystallization of benzimidazole with benzene 1,3,5-tricarboxylic acid in slightly basic medium afforded the title compound, C7H7N2+·C9H5O6−·3H2O, in which one of the imidazole N atom is protonated and one carboxylic group of aromatic acid is deprotonated. In the intermolecular N—H⋯O hydrogen-bonding connects the two organic components into dimers, which are further linked into a three-dimensional network by O—H⋯O and N—H⋯O interactions between the water molecules and the dimers.
Related literature
For molecular self-assembly by non-covalent interactions and its potential applications, see: Remenar et al. (2003); Oxtoby et al. (2005); Zaworotko (2001). For the benzimidazole-based supramolecular aggregate formed by π–π stacking and hydrogen-bonding interactions, see Gao et al. (2004).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2003); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536810023305/nc2189sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810023305/nc2189Isup2.hkl
A mixture containing H3btc (21.0 mg, 0.1 mmol), bim (11.8 mg, 0.1 mmol), and NaOH (4.0 mg, 0.1 mmol) was dissolved in a mixed methanol-H2O solution (v: v = 1:1, 10.0 ml). Then, the mixture was transferred into a Teflon-lined reactor (23.0 ml) and heated to 70 oC for 48 hrs. After the mixture was cooled to room temperature at a rate of 6 oC h-1, colorless block-shaped crystals suitable for X-ray diffraction were obtained directly. Yield: 56% based on bim. Anal.Calcd for C16H18N2O9,C,50.26; H, 4.75; N, 7.33%. Found: C, 50.32; H, 4.78; N,7.36%.
The C-H, N-H and hydroxy H atoms were located in difference maps, but were placed in calculated positions (O-H allowed to rotate but not to tip) and treated as riding, with C – H = 0.93, O – H = 0.82 and N – H = 0.86 Å. The water H atoms were located in difference map and were refined using restraints. All H were refined isotropic with [Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(O)].
Data collection: APEX2 (Bruker, 2003); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. Crystal structure of the title compound with view along the a-axis. Hydrogen bonding is shown as dashed lines. |
C7H7N2+·C9H5O6−·3H2O | Z = 1 |
Mr = 382.32 | F(000) = 200 |
Triclinic, P1 | Dx = 1.465 Mg m−3 |
Hall symbol: P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8478 (2) Å | Cell parameters from 1795 reflections |
b = 10.2231 (6) Å | θ = 2.8–27.9° |
c = 11.2982 (7) Å | µ = 0.12 mm−1 |
α = 85.522 (1)° | T = 296 K |
β = 80.707 (1)° | Block, colourless |
γ = 81.826 (1)° | 0.24 × 0.22 × 0.20 mm |
V = 433.45 (4) Å3 |
Bruker APEXII CCD area-detector diffractometer | 1536 independent reflections |
Radiation source: fine-focus sealed tube | 1478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.008 |
phi and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→4 |
Tmin = 0.971, Tmax = 0.976 | k = −12→5 |
2240 measured reflections | l = −13→13 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0522P)2 + 0.0236P] where P = (Fo2 + 2Fc2)/3 |
1536 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.14 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
C7H7N2+·C9H5O6−·3H2O | γ = 81.826 (1)° |
Mr = 382.32 | V = 433.45 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 3.8478 (2) Å | Mo Kα radiation |
b = 10.2231 (6) Å | µ = 0.12 mm−1 |
c = 11.2982 (7) Å | T = 296 K |
α = 85.522 (1)° | 0.24 × 0.22 × 0.20 mm |
β = 80.707 (1)° |
Bruker APEXII CCD area-detector diffractometer | 1536 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1478 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.976 | Rint = 0.008 |
2240 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 3 restraints |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.14 e Å−3 |
1536 reflections | Δρmin = −0.19 e Å−3 |
246 parameters |
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 | 0.8287 (5) | 0.63795 (18) | 1.20720 (14) | 0.0482 (4) | |
O2 | 0.9531 (6) | 0.44710 (18) | 1.11874 (15) | 0.0581 (5) | |
O3 | 1.2332 (6) | 0.50067 (17) | 0.65819 (16) | 0.0552 (5) | |
O4 | 0.9893 (5) | 0.68726 (18) | 0.57532 (15) | 0.0546 (5) | |
H4 | 1.1005 | 0.6561 | 0.5135 | 0.082* | |
O5 | 0.2872 (6) | 1.03786 (17) | 0.80326 (17) | 0.0596 (5) | |
O6 | 0.1819 (5) | 1.01258 (17) | 1.00192 (16) | 0.0544 (5) | |
H6 | 0.0662 | 1.0858 | 0.9946 | 0.082* | |
N1 | −0.0881 (6) | 0.2463 (2) | 0.52127 (19) | 0.0457 (5) | |
H1 | −0.1644 | 0.2470 | 0.5971 | 0.055* | |
N2 | 0.0014 (6) | 0.3109 (2) | 0.33346 (19) | 0.0458 (5) | |
H2 | −0.0077 | 0.3595 | 0.2681 | 0.055* | |
C1 | 0.1306 (6) | 0.1435 (2) | 0.4635 (2) | 0.0384 (5) | |
C2 | 0.1892 (6) | 0.1855 (2) | 0.3429 (2) | 0.0387 (5) | |
C3 | 0.3998 (7) | 0.1058 (3) | 0.2576 (2) | 0.0497 (6) | |
H3 | 0.4411 | 0.1336 | 0.1769 | 0.060* | |
C4 | 0.5439 (7) | −0.0170 (3) | 0.2996 (3) | 0.0587 (7) | |
H4A | 0.6863 | −0.0735 | 0.2455 | 0.070* | |
C5 | 0.4822 (8) | −0.0587 (3) | 0.4207 (3) | 0.0592 (8) | |
H5 | 0.5843 | −0.1424 | 0.4450 | 0.071* | |
C6 | 0.2766 (7) | 0.0196 (3) | 0.5047 (3) | 0.0507 (6) | |
H6A | 0.2364 | −0.0086 | 0.5854 | 0.061* | |
C7 | −0.1607 (7) | 0.3433 (2) | 0.4406 (2) | 0.0482 (6) | |
H7 | −0.3052 | 0.4227 | 0.4574 | 0.058* | |
C8 | 0.7899 (5) | 0.6418 (2) | 1.00125 (19) | 0.0329 (5) | |
C9 | 0.9324 (5) | 0.5896 (2) | 0.89162 (19) | 0.0325 (4) | |
H9 | 1.0628 | 0.5057 | 0.8895 | 0.039* | |
C10 | 0.8824 (6) | 0.6614 (2) | 0.78491 (19) | 0.0320 (4) | |
C11 | 0.6801 (5) | 0.7855 (2) | 0.78785 (19) | 0.0332 (4) | |
H11 | 0.6451 | 0.8336 | 0.7165 | 0.040* | |
C12 | 0.5300 (6) | 0.8377 (2) | 0.8973 (2) | 0.0339 (5) | |
C13 | 0.5874 (5) | 0.7666 (2) | 1.00353 (19) | 0.0336 (4) | |
H13 | 0.4907 | 0.8023 | 1.0768 | 0.040* | |
C14 | 0.8615 (6) | 0.5697 (2) | 1.11777 (19) | 0.0367 (5) | |
C15 | 1.0532 (6) | 0.6071 (2) | 0.66716 (18) | 0.0358 (5) | |
C16 | 0.3216 (6) | 0.9717 (2) | 0.8957 (2) | 0.0388 (5) | |
O7 | 0.8307 (6) | 0.24730 (19) | 0.9861 (2) | 0.0668 (6) | |
H7A | 0.8766 | 0.3119 | 1.0213 | 0.100* | |
H7B | 0.7602 | 0.2814 | 0.9216 | 0.100* | |
O8 | 0.5721 (6) | 0.27703 (19) | 0.75910 (17) | 0.0584 (5) | |
H8A | 0.4356 | 0.2174 | 0.7739 | 0.088* | |
H8B | 0.4373 | 0.3479 | 0.7446 | 0.088* | |
O9 | 0.2592 (5) | 0.60054 (19) | 0.37164 (15) | 0.0520 (5) | |
H9A | 0.1063 | 0.6114 | 0.3240 | 0.078* | |
H9B | 0.4479 | 0.6232 | 0.3300 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0596 (10) | 0.0565 (10) | 0.0271 (8) | 0.0005 (8) | −0.0094 (7) | −0.0032 (7) |
O2 | 0.0961 (15) | 0.0393 (9) | 0.0363 (9) | 0.0075 (9) | −0.0217 (9) | 0.0072 (7) |
O3 | 0.0797 (12) | 0.0418 (10) | 0.0325 (9) | 0.0211 (9) | −0.0007 (8) | 0.0009 (7) |
O4 | 0.0773 (12) | 0.0496 (10) | 0.0247 (8) | 0.0198 (9) | 0.0002 (8) | 0.0047 (7) |
O5 | 0.0951 (15) | 0.0369 (9) | 0.0398 (10) | 0.0166 (9) | −0.0136 (9) | 0.0021 (8) |
O6 | 0.0812 (13) | 0.0359 (9) | 0.0385 (9) | 0.0153 (8) | −0.0060 (9) | −0.0032 (7) |
N1 | 0.0534 (11) | 0.0466 (12) | 0.0355 (11) | −0.0055 (9) | −0.0028 (9) | −0.0024 (9) |
N2 | 0.0611 (13) | 0.0366 (10) | 0.0406 (11) | −0.0060 (9) | −0.0160 (10) | 0.0087 (8) |
C1 | 0.0440 (11) | 0.0384 (11) | 0.0346 (11) | −0.0078 (9) | −0.0119 (9) | 0.0034 (9) |
C2 | 0.0462 (12) | 0.0371 (12) | 0.0355 (11) | −0.0099 (10) | −0.0131 (10) | 0.0036 (9) |
C3 | 0.0536 (14) | 0.0597 (16) | 0.0371 (13) | −0.0118 (12) | −0.0048 (11) | −0.0075 (12) |
C4 | 0.0533 (15) | 0.0527 (16) | 0.072 (2) | −0.0013 (12) | −0.0138 (14) | −0.0202 (14) |
C5 | 0.0596 (16) | 0.0382 (13) | 0.082 (2) | 0.0024 (11) | −0.0281 (15) | 0.0001 (14) |
C6 | 0.0617 (15) | 0.0440 (14) | 0.0493 (14) | −0.0071 (12) | −0.0229 (12) | 0.0107 (11) |
C7 | 0.0556 (14) | 0.0381 (13) | 0.0503 (15) | −0.0012 (11) | −0.0105 (12) | −0.0021 (11) |
C8 | 0.0370 (11) | 0.0335 (11) | 0.0276 (10) | −0.0049 (9) | −0.0052 (8) | 0.0024 (8) |
C9 | 0.0373 (11) | 0.0297 (10) | 0.0282 (10) | 0.0016 (8) | −0.0046 (8) | 0.0012 (8) |
C10 | 0.0376 (10) | 0.0315 (10) | 0.0254 (10) | −0.0016 (8) | −0.0046 (8) | 0.0009 (8) |
C11 | 0.0397 (10) | 0.0307 (10) | 0.0274 (11) | −0.0001 (8) | −0.0064 (8) | 0.0032 (8) |
C12 | 0.0388 (10) | 0.0297 (10) | 0.0337 (12) | −0.0030 (8) | −0.0085 (9) | −0.0006 (9) |
C13 | 0.0394 (11) | 0.0321 (11) | 0.0280 (10) | −0.0007 (9) | −0.0040 (8) | −0.0028 (8) |
C14 | 0.0421 (11) | 0.0389 (12) | 0.0267 (11) | 0.0014 (9) | −0.0061 (9) | 0.0025 (9) |
C15 | 0.0412 (11) | 0.0350 (12) | 0.0281 (11) | 0.0024 (9) | −0.0038 (9) | 0.0021 (9) |
C16 | 0.0485 (12) | 0.0308 (11) | 0.0363 (12) | 0.0012 (9) | −0.0093 (10) | −0.0037 (10) |
O7 | 0.0998 (16) | 0.0385 (9) | 0.0595 (12) | 0.0173 (9) | −0.0252 (11) | −0.0076 (9) |
O8 | 0.0766 (13) | 0.0444 (10) | 0.0464 (10) | 0.0072 (8) | −0.0049 (9) | 0.0089 (8) |
O9 | 0.0559 (10) | 0.0711 (12) | 0.0274 (8) | −0.0039 (9) | −0.0054 (7) | −0.0029 (8) |
O1—C14 | 1.252 (3) | C5—H5 | 0.9300 |
O2—C14 | 1.252 (3) | C6—H6A | 0.9300 |
O3—C15 | 1.206 (3) | C7—H7 | 0.9300 |
O4—C15 | 1.304 (3) | C8—C9 | 1.386 (3) |
O4—H4 | 0.8200 | C8—C13 | 1.397 (3) |
O5—C16 | 1.214 (3) | C8—C14 | 1.503 (3) |
O6—C16 | 1.308 (3) | C9—C10 | 1.388 (3) |
O6—H6 | 0.8200 | C9—H9 | 0.9300 |
N1—C7 | 1.325 (3) | C10—C11 | 1.390 (3) |
N1—C1 | 1.384 (3) | C10—C15 | 1.496 (3) |
N1—H1 | 0.8600 | C11—C12 | 1.390 (3) |
N2—C7 | 1.313 (4) | C11—H11 | 0.9300 |
N2—C2 | 1.384 (3) | C12—C13 | 1.385 (3) |
N2—H2 | 0.8600 | C12—C16 | 1.487 (3) |
C1—C6 | 1.388 (3) | C13—H13 | 0.9300 |
C1—C2 | 1.389 (3) | O7—H7A | 0.8500 |
C2—C3 | 1.390 (4) | O7—H7B | 0.8499 |
C3—C4 | 1.378 (4) | O8—H8A | 0.8500 |
C3—H3 | 0.9300 | O8—H8B | 0.8500 |
C4—C5 | 1.394 (5) | O9—H9A | 0.8500 |
C4—H4A | 0.9300 | O9—H9B | 0.8500 |
C5—C6 | 1.366 (5) | ||
C15—O4—H4 | 109.5 | C9—C8—C14 | 121.44 (18) |
C16—O6—H6 | 109.5 | C13—C8—C14 | 119.20 (18) |
C7—N1—C1 | 108.8 (2) | C8—C9—C10 | 120.62 (18) |
C7—N1—H1 | 125.6 | C8—C9—H9 | 119.7 |
C1—N1—H1 | 125.6 | C10—C9—H9 | 119.7 |
C7—N2—C2 | 108.8 (2) | C9—C10—C11 | 119.75 (19) |
C7—N2—H2 | 125.6 | C9—C10—C15 | 120.17 (18) |
C2—N2—H2 | 125.6 | C11—C10—C15 | 120.06 (19) |
N1—C1—C6 | 132.4 (2) | C12—C11—C10 | 120.10 (19) |
N1—C1—C2 | 105.9 (2) | C12—C11—H11 | 120.0 |
C6—C1—C2 | 121.7 (2) | C10—C11—H11 | 120.0 |
N2—C2—C1 | 106.4 (2) | C13—C12—C11 | 119.81 (19) |
N2—C2—C3 | 132.0 (2) | C13—C12—C16 | 122.13 (19) |
C1—C2—C3 | 121.5 (2) | C11—C12—C16 | 118.02 (18) |
C4—C3—C2 | 116.2 (2) | C12—C13—C8 | 120.39 (19) |
C4—C3—H3 | 121.9 | C12—C13—H13 | 119.8 |
C2—C3—H3 | 121.9 | C8—C13—H13 | 119.8 |
C3—C4—C5 | 121.9 (3) | O1—C14—O2 | 124.6 (2) |
C3—C4—H4A | 119.1 | O1—C14—C8 | 116.94 (19) |
C5—C4—H4A | 119.1 | O2—C14—C8 | 118.41 (19) |
C6—C5—C4 | 122.0 (3) | O3—C15—O4 | 123.5 (2) |
C6—C5—H5 | 119.0 | O3—C15—C10 | 123.5 (2) |
C4—C5—H5 | 119.0 | O4—C15—C10 | 113.00 (18) |
C5—C6—C1 | 116.6 (3) | O5—C16—O6 | 123.0 (2) |
C5—C6—H6A | 121.7 | O5—C16—C12 | 122.6 (2) |
C1—C6—H6A | 121.7 | O6—C16—C12 | 114.39 (19) |
N2—C7—N1 | 110.0 (2) | H7A—O7—H7B | 105.2 |
N2—C7—H7 | 125.0 | H8A—O8—H8B | 105.1 |
N1—C7—H7 | 125.0 | H9A—O9—H9B | 105.1 |
C9—C8—C13 | 119.31 (19) | ||
C7—N1—C1—C6 | −178.5 (2) | C9—C10—C11—C12 | 0.3 (3) |
C7—N1—C1—C2 | 0.8 (3) | C15—C10—C11—C12 | −178.1 (2) |
C7—N2—C2—C1 | 0.0 (3) | C10—C11—C12—C13 | 1.1 (3) |
C7—N2—C2—C3 | 179.4 (2) | C10—C11—C12—C16 | 178.9 (2) |
N1—C1—C2—N2 | −0.4 (2) | C11—C12—C13—C8 | −1.2 (3) |
C6—C1—C2—N2 | 178.9 (2) | C16—C12—C13—C8 | −178.9 (2) |
N1—C1—C2—C3 | −179.9 (2) | C9—C8—C13—C12 | −0.1 (3) |
C6—C1—C2—C3 | −0.6 (3) | C14—C8—C13—C12 | 177.29 (18) |
N2—C2—C3—C4 | −178.9 (2) | C9—C8—C14—O1 | 156.9 (2) |
C1—C2—C3—C4 | 0.4 (3) | C13—C8—C14—O1 | −20.4 (3) |
C2—C3—C4—C5 | −0.1 (4) | C9—C8—C14—O2 | −22.2 (3) |
C3—C4—C5—C6 | −0.2 (4) | C13—C8—C14—O2 | 160.5 (2) |
C4—C5—C6—C1 | 0.1 (4) | C9—C10—C15—O3 | 1.2 (3) |
N1—C1—C6—C5 | 179.4 (3) | C11—C10—C15—O3 | 179.6 (2) |
C2—C1—C6—C5 | 0.3 (3) | C9—C10—C15—O4 | −178.3 (2) |
C2—N2—C7—N1 | 0.5 (3) | C11—C10—C15—O4 | 0.1 (3) |
C1—N1—C7—N2 | −0.8 (3) | C13—C12—C16—O5 | 175.6 (2) |
C13—C8—C9—C10 | 1.5 (3) | C11—C12—C16—O5 | −2.1 (3) |
C14—C8—C9—C10 | −175.82 (19) | C13—C12—C16—O6 | −3.8 (3) |
C8—C9—C10—C11 | −1.6 (3) | C11—C12—C16—O6 | 178.4 (2) |
C8—C9—C10—C15 | 176.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O9i | 0.82 | 1.73 | 2.539 (2) | 169 |
O6—H6···O7ii | 0.82 | 1.77 | 2.589 (2) | 176 |
N1—H1···O8iii | 0.86 | 1.97 | 2.812 (3) | 167 |
N2—H2···O2iv | 0.86 | 1.87 | 2.721 (3) | 173 |
O7—H7A···O2 | 0.85 | 1.92 | 2.760 (3) | 173 |
O7—H7B···O8 | 0.85 | 2.09 | 2.877 (3) | 155 |
O8—H8A···O5v | 0.85 | 1.99 | 2.797 (3) | 159 |
O8—H8B···O3iii | 0.85 | 1.92 | 2.730 (2) | 160 |
O9—H9A···O1iv | 0.85 | 1.81 | 2.654 (2) | 173 |
O9—H9B···O1vi | 0.85 | 1.86 | 2.685 (3) | 163 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y+1, z; (iii) x−1, y, z; (iv) x−1, y, z−1; (v) x, y−1, z; (vi) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C7H7N2+·C9H5O6−·3H2O |
Mr | 382.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 3.8478 (2), 10.2231 (6), 11.2982 (7) |
α, β, γ (°) | 85.522 (1), 80.707 (1), 81.826 (1) |
V (Å3) | 433.45 (4) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.24 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.971, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2240, 1536, 1478 |
Rint | 0.008 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.073, 1.04 |
No. of reflections | 1536 |
No. of parameters | 246 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.19 |
Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O9i | 0.82 | 1.73 | 2.539 (2) | 168.8 |
O6—H6···O7ii | 0.82 | 1.77 | 2.589 (2) | 176.3 |
N1—H1···O8iii | 0.86 | 1.97 | 2.812 (3) | 167.0 |
N2—H2···O2iv | 0.86 | 1.87 | 2.721 (3) | 172.7 |
O7—H7A···O2 | 0.85 | 1.92 | 2.760 (3) | 172.8 |
O7—H7B···O8 | 0.85 | 2.09 | 2.877 (3) | 154.6 |
O8—H8A···O5v | 0.85 | 1.99 | 2.797 (3) | 159.1 |
O8—H8B···O3iii | 0.85 | 1.92 | 2.730 (2) | 160.0 |
O9—H9A···O1iv | 0.85 | 1.81 | 2.654 (2) | 172.5 |
O9—H9B···O1vi | 0.85 | 1.86 | 2.685 (3) | 162.6 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y+1, z; (iii) x−1, y, z; (iv) x−1, y, z−1; (v) x, y−1, z; (vi) x, y, z−1. |
Acknowledgements
The authors gratefully acknowledge financial support from the Tianjin Key Laboratory of Structure and Performance for Functional Molecule.
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Recently, molecular self-assembly by non-covalent interactions has attacted considerable interest in supramolecular chemistry and crystal engineering due to their possible potential applications as functional materials (Zaworotko, 2001), in molecular recognition (Oxtoby et al., 2005), and pharmaceutical chemistry (Remenar et al., 2003). Obviously, the conguated organic components with rich carboxylate or amino groups have became good blocks for the construction of self-assembly systems, since hydrogen-bonding and π··· π interactions are the main driven forces of the assembly process. In this context benzimidazole (bim) and its derivatives have been used as promising building blocks for the construction of supramolecular aggregates. As a continuation of this work bim and 1,3,5-benzenetricarboxylic acid (H3btc) were reacted in slightly basic medium and the product were identified by single crystal X-ray diffraction.
The asymmetric unit of the title compound comprises one Hbim+ cation, one monodeprotonated H2btc- anion and three water molecules all of the located in general positions (Fig. 1). The two carboxyl groups are located within the plane of the aromatic ring, whereas the deprotonated carboxylate group is slightly twisted out of the ring plane. The dihedral angle between the aromatic and the benzimidazole rings amount to 6.84 (5)o.
In the crystal structure, the Hbim+ cations and H2btc- anions are connected into dimers by N–H···O hydrogen-bonding between the N—H H atoms and the carboxylate group (Table 1). These dimers are further connected by O–H···O and N–H···O hydrogen bonding between the water molecules, the carboxyl and carboxylate groups as well as the N-H H atoms into a three-dimensional hydrogen bonded network (Figure 2 and Table 1). In this interactions the water molecules act as hydrogen bond donor and acceptor.