Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031273/ez2080sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031273/ez2080Isup2.hkl |
CCDC reference: 642280
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.105
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
o-Phenylenediamine (5.40 g, 0.05 mol) and succinic acid (2.95 g, 0.025 mol) were refluxed for twelve hours in 50 mL of 4M HCl. The reaction mixture was then cooled for one day and the blue crystalline dihydrochloride was removed by filtration and dried. Crystals of the dihydrochloride suitable for X-ray diffraction were obtained by dissolving in water and allowing the solution to stand at room temperature for several days (Wang et al., 1957). Yield: 43%.
Water H atoms were located in a difference Fourier synthesis and refined 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 with Uiso(H) = 1.2 Ueq (C, N).
We present an 'axle' type polyaromatic compound (I) that contains 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).
The molecular structure of (I), shown in Fig. 1, consists of an organic cation, Cl- anions and lattice water molecules. The two benzimidazolyl rings in the organic cation are not co-planar, with a dihedral angle of 27.77 (6)° between them. Molecules are linked via a network of hydrogen bonds (N1—H1···O2, O2—H2C···Cl1, N2—H2A···Cl1, N3—H3A···Cl2, O1—H1B···Cl2, N4—H4A···O1, O1—H1A···O3, O3—H3B···Cl1; Table 1).
π···π stacking interactions are observed between nearly parallel benzimidazolyl benzene rings. The centroid-to-centroid distance between C1–C6 benzene rings is 3.635 (3) Å (symmetry code: –X,-Y,1-Z), while between C11–C16 benzene rings it is 3.817 (3) Å (symmetry codes:1-X,1-Y,-Z). In addition, an N—H···π interaction occurs between adjacent benzimidazolyl groups, with an N1—H1···Cg(3) angle of 79.89°, and H1···Cg(3) and N1···Cg(3) distances of 3.3964Å and 3.354 (3) Å, respectively [Cg(3) is the centroid of the C1–C6-benzene (symmetry codes:1-X,-Y,1-Z)].
For related literature, see: Day & Arnold (2000); Day et al. (2002); Freeman et al. (1981); Kim et al. (2000); Wang & Joullié (1957).
Data collection: APEX2 (Bruker, Year?); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. The molecular structure of (I), shown with the atom numbering scheme and 50% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds. |
C16H16N42+·2Cl−·4H2O | Z = 2 |
Mr = 407.29 | F(000) = 428 |
Triclinic, P1 | Dx = 1.393 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.174 (6) Å | Cell parameters from 3317 reflections |
b = 9.652 (8) Å | θ = 1.4–25.0° |
c = 15.411 (13) Å | µ = 0.36 mm−1 |
α = 80.504 (8)° | T = 293 K |
β = 79.684 (9)° | Prism, colourless |
γ = 68.520 (8)° | 0.17 × 0.14 × 0.08 mm |
V = 971.2 (14) Å3 |
Bruker APEXII CCD area-detector diffractometer | 3317 independent reflections |
Radiation source: fine-focus sealed tube | 2933 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick,1997) | h = −8→8 |
Tmin = 0.941, Tmax = 0.972 | k = −11→11 |
6584 measured reflections | l = −16→18 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.2765P] where P = (Fo2 + 2Fc2)/3 |
3317 reflections | (Δ/σ)max = 0.001 |
237 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C16H16N42+·2Cl−·4H2O | γ = 68.520 (8)° |
Mr = 407.29 | V = 971.2 (14) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.174 (6) Å | Mo Kα radiation |
b = 9.652 (8) Å | µ = 0.36 mm−1 |
c = 15.411 (13) Å | T = 293 K |
α = 80.504 (8)° | 0.17 × 0.14 × 0.08 mm |
β = 79.684 (9)° |
Bruker APEXII CCD area-detector diffractometer | 3317 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick,1997) | 2933 reflections with I > 2σ(I) |
Tmin = 0.941, Tmax = 0.972 | Rint = 0.014 |
6584 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.20 e Å−3 |
3317 reflections | Δρmin = −0.27 e Å−3 |
237 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 | ||
C1 | 0.6983 (2) | 1.03103 (18) | 0.52524 (10) | 0.0288 (3) | |
C2 | 0.6639 (3) | 1.16652 (19) | 0.47131 (12) | 0.0359 (4) | |
H2 | 0.5807 | 1.2572 | 0.4920 | 0.043* | |
C3 | 0.7605 (3) | 1.1583 (2) | 0.38534 (12) | 0.0385 (4) | |
H3 | 0.7424 | 1.2464 | 0.3473 | 0.046* | |
C4 | 0.8855 (3) | 1.0215 (2) | 0.35315 (11) | 0.0391 (4) | |
H4 | 0.9459 | 1.0212 | 0.2945 | 0.047* | |
C5 | 0.9199 (3) | 0.8880 (2) | 0.40694 (12) | 0.0374 (4) | |
H5 | 1.0028 | 0.7974 | 0.3861 | 0.045* | |
C6 | 0.8248 (2) | 0.89511 (18) | 0.49381 (11) | 0.0302 (4) | |
C7 | 0.7063 (2) | 0.84969 (19) | 0.63476 (11) | 0.0357 (4) | |
C8 | 0.6641 (3) | 0.7702 (2) | 0.72354 (13) | 0.0472 (5) | |
H8A | 0.6060 | 0.6970 | 0.7165 | 0.057* | |
H8B | 0.5654 | 0.8419 | 0.7610 | 0.057* | |
C9 | 0.8508 (3) | 0.6921 (2) | 0.76849 (12) | 0.0480 (5) | |
H9A | 0.9461 | 0.6159 | 0.7328 | 0.058* | |
H9B | 0.9136 | 0.7641 | 0.7721 | 0.058* | |
C10 | 0.8068 (3) | 0.6206 (2) | 0.85950 (11) | 0.0367 (4) | |
C11 | 0.7655 (2) | 0.45577 (18) | 0.97231 (11) | 0.0300 (4) | |
C12 | 0.7552 (3) | 0.32862 (19) | 1.02773 (12) | 0.0373 (4) | |
H12 | 0.7750 | 0.2396 | 1.0055 | 0.045* | |
C13 | 0.7139 (3) | 0.3424 (2) | 1.11733 (12) | 0.0427 (4) | |
H13 | 0.7079 | 0.2596 | 1.1567 | 0.051* | |
C14 | 0.6805 (3) | 0.4770 (2) | 1.15129 (12) | 0.0435 (5) | |
H14 | 0.6515 | 0.4812 | 1.2123 | 0.052* | |
C15 | 0.6896 (3) | 0.6028 (2) | 1.09654 (12) | 0.0402 (4) | |
H15 | 0.6663 | 0.6924 | 1.1188 | 0.048* | |
C16 | 0.7356 (2) | 0.58891 (18) | 1.00602 (11) | 0.0312 (4) | |
N1 | 0.6283 (2) | 0.99668 (16) | 0.61347 (9) | 0.0330 (3) | |
H1 | 0.5477 | 1.0603 | 0.6485 | 0.040* | |
N2 | 0.8250 (2) | 0.78573 (15) | 0.56483 (10) | 0.0369 (3) | |
H2A | 0.8914 | 0.6915 | 0.5638 | 0.044* | |
N3 | 0.7621 (2) | 0.68854 (16) | 0.93284 (9) | 0.0367 (3) | |
H3A | 0.7512 | 0.7798 | 0.9347 | 0.044* | |
N4 | 0.8080 (2) | 0.48110 (16) | 0.88072 (9) | 0.0352 (3) | |
H4A | 0.8312 | 0.4171 | 0.8438 | 0.042* | |
O1 | 0.8156 (2) | 0.29177 (16) | 0.76720 (9) | 0.0541 (4) | |
H1A | 0.7466 | 0.3352 | 0.7192 | 0.065* | |
H1B | 0.7641 | 0.2151 | 0.7953 | 0.065* | |
O2 | 0.3755 (2) | 0.19384 (16) | 0.72672 (9) | 0.0550 (4) | |
H2B | 0.3037 | 0.1536 | 0.7691 | 0.066* | |
H2C | 0.2837 | 0.2748 | 0.6944 | 0.066* | |
O3 | 0.6201 (3) | 0.46531 (18) | 0.62377 (10) | 0.0628 (4) | |
H3B | 0.4915 | 0.4593 | 0.6121 | 0.122 (12)* | |
H3C | 0.6796 | 0.4806 | 0.5679 | 0.107 (11)* | |
O4 | 0.7843 (3) | 0.9552 (2) | 0.12510 (12) | 0.0885 (6) | |
H4B | 0.9091 | 0.9725 | 0.1156 | 0.106* | |
H4C | 0.7735 | 0.9600 | 0.0675 | 0.106* | |
Cl1 | 0.18700 (7) | 0.47137 (5) | 0.58431 (3) | 0.05045 (17) | |
Cl2 | 0.76500 (10) | 1.01372 (6) | 0.90382 (4) | 0.0651 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0309 (8) | 0.0306 (8) | 0.0258 (8) | −0.0118 (7) | −0.0047 (6) | −0.0015 (6) |
C2 | 0.0413 (9) | 0.0278 (9) | 0.0378 (10) | −0.0107 (7) | −0.0078 (8) | −0.0018 (7) |
C3 | 0.0463 (10) | 0.0361 (9) | 0.0349 (10) | −0.0198 (8) | −0.0104 (8) | 0.0092 (7) |
C4 | 0.0426 (10) | 0.0504 (11) | 0.0266 (9) | −0.0221 (8) | −0.0011 (7) | 0.0000 (8) |
C5 | 0.0364 (9) | 0.0363 (9) | 0.0364 (10) | −0.0105 (7) | 0.0026 (7) | −0.0085 (8) |
C6 | 0.0297 (8) | 0.0285 (8) | 0.0309 (9) | −0.0103 (7) | −0.0036 (6) | 0.0013 (7) |
C7 | 0.0309 (9) | 0.0392 (10) | 0.0323 (9) | −0.0110 (7) | −0.0039 (7) | 0.0056 (7) |
C8 | 0.0406 (10) | 0.0528 (12) | 0.0389 (11) | −0.0150 (9) | −0.0013 (8) | 0.0136 (9) |
C9 | 0.0447 (11) | 0.0604 (13) | 0.0349 (10) | −0.0207 (9) | −0.0035 (8) | 0.0101 (9) |
C10 | 0.0339 (9) | 0.0419 (10) | 0.0322 (9) | −0.0139 (8) | −0.0061 (7) | 0.0053 (8) |
C11 | 0.0278 (8) | 0.0336 (9) | 0.0280 (8) | −0.0110 (7) | −0.0038 (6) | −0.0007 (7) |
C12 | 0.0350 (9) | 0.0315 (9) | 0.0440 (11) | −0.0122 (7) | −0.0044 (7) | 0.0009 (8) |
C13 | 0.0373 (10) | 0.0435 (11) | 0.0402 (11) | −0.0138 (8) | −0.0026 (8) | 0.0124 (8) |
C14 | 0.0407 (10) | 0.0581 (12) | 0.0261 (9) | −0.0144 (9) | −0.0010 (7) | 0.0008 (8) |
C15 | 0.0437 (10) | 0.0432 (10) | 0.0354 (10) | −0.0147 (8) | −0.0059 (8) | −0.0089 (8) |
C16 | 0.0313 (8) | 0.0325 (9) | 0.0318 (9) | −0.0140 (7) | −0.0073 (7) | 0.0016 (7) |
N1 | 0.0343 (7) | 0.0344 (8) | 0.0267 (7) | −0.0093 (6) | −0.0010 (6) | −0.0027 (6) |
N2 | 0.0365 (8) | 0.0255 (7) | 0.0391 (8) | −0.0055 (6) | 0.0001 (6) | 0.0047 (6) |
N3 | 0.0455 (8) | 0.0307 (7) | 0.0359 (8) | −0.0182 (6) | −0.0060 (6) | 0.0035 (6) |
N4 | 0.0392 (8) | 0.0383 (8) | 0.0277 (8) | −0.0134 (6) | −0.0027 (6) | −0.0038 (6) |
O1 | 0.0742 (10) | 0.0461 (8) | 0.0385 (8) | −0.0168 (7) | −0.0033 (7) | −0.0088 (6) |
O2 | 0.0685 (9) | 0.0482 (8) | 0.0396 (8) | −0.0106 (7) | −0.0032 (7) | −0.0074 (6) |
O3 | 0.0675 (10) | 0.0706 (11) | 0.0457 (9) | −0.0211 (8) | −0.0100 (7) | 0.0020 (7) |
O4 | 0.1155 (16) | 0.1051 (15) | 0.0603 (11) | −0.0637 (13) | −0.0186 (10) | 0.0163 (10) |
Cl1 | 0.0523 (3) | 0.0349 (3) | 0.0540 (3) | −0.0059 (2) | −0.0056 (2) | −0.0004 (2) |
Cl2 | 0.0916 (4) | 0.0397 (3) | 0.0694 (4) | −0.0299 (3) | −0.0209 (3) | 0.0068 (3) |
C1—N1 | 1.393 (2) | C11—C12 | 1.393 (3) |
C1—C2 | 1.393 (2) | C11—C16 | 1.395 (3) |
C1—C6 | 1.400 (2) | C12—C13 | 1.377 (3) |
C2—C3 | 1.381 (3) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.404 (3) |
C3—C4 | 1.409 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.375 (3) |
C4—C5 | 1.376 (3) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.392 (3) |
C5—C6 | 1.390 (3) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—N3 | 1.390 (2) |
C6—N2 | 1.389 (2) | N1—H1 | 0.8600 |
C7—N1 | 1.328 (2) | N2—H2A | 0.8600 |
C7—N2 | 1.332 (2) | N3—H3A | 0.8600 |
C7—C8 | 1.493 (3) | N4—H4A | 0.8600 |
C8—C9 | 1.504 (3) | O1—H1A | 0.9193 |
C8—H8A | 0.9700 | O1—H1B | 0.9531 |
C8—H8B | 0.9700 | O2—H2B | 0.8859 |
C9—C10 | 1.491 (3) | O2—H2C | 0.9513 |
C9—H9A | 0.9700 | O3—H3B | 0.9944 |
C9—H9B | 0.9700 | O3—H3C | 0.9044 |
C10—N4 | 1.330 (3) | O4—H4B | 0.9517 |
C10—N3 | 1.331 (2) | O4—H4C | 0.8972 |
C11—N4 | 1.390 (2) | ||
N1—C1—C2 | 131.94 (15) | N3—C10—C9 | 124.31 (18) |
N1—C1—C6 | 106.44 (14) | N4—C11—C12 | 131.65 (16) |
C2—C1—C6 | 121.62 (16) | N4—C11—C16 | 106.66 (15) |
C3—C2—C1 | 116.08 (16) | C12—C11—C16 | 121.67 (16) |
C3—C2—H2 | 122.0 | C13—C12—C11 | 116.09 (17) |
C1—C2—H2 | 122.0 | C13—C12—H12 | 122.0 |
C2—C3—C4 | 122.42 (16) | C11—C12—H12 | 122.0 |
C2—C3—H3 | 118.8 | C12—C13—C14 | 122.31 (17) |
C4—C3—H3 | 118.8 | C12—C13—H13 | 118.8 |
C5—C4—C3 | 121.21 (17) | C14—C13—H13 | 118.8 |
C5—C4—H4 | 119.4 | C15—C14—C13 | 121.59 (18) |
C3—C4—H4 | 119.4 | C15—C14—H14 | 119.2 |
C4—C5—C6 | 116.86 (16) | C13—C14—H14 | 119.2 |
C4—C5—H5 | 121.6 | C14—C15—C16 | 116.44 (17) |
C6—C5—H5 | 121.6 | C14—C15—H15 | 121.8 |
N2—C6—C5 | 132.39 (16) | C16—C15—H15 | 121.8 |
N2—C6—C1 | 105.81 (15) | N3—C16—C15 | 132.35 (16) |
C5—C6—C1 | 121.80 (16) | N3—C16—C11 | 105.79 (15) |
N1—C7—N2 | 109.51 (15) | C15—C16—C11 | 121.87 (16) |
N1—C7—C8 | 124.61 (16) | C7—N1—C1 | 108.89 (14) |
N2—C7—C8 | 125.88 (17) | C7—N1—H1 | 125.6 |
C7—C8—C9 | 112.55 (16) | C1—N1—H1 | 125.6 |
C7—C8—H8A | 109.1 | C7—N2—C6 | 109.36 (15) |
C9—C8—H8A | 109.1 | C7—N2—H2A | 125.3 |
C7—C8—H8B | 109.1 | C6—N2—H2A | 125.3 |
C9—C8—H8B | 109.1 | C10—N3—C16 | 109.32 (15) |
H8A—C8—H8B | 107.8 | C10—N3—H3A | 125.3 |
C10—C9—C8 | 112.61 (16) | C16—N3—H3A | 125.3 |
C10—C9—H9A | 109.1 | C10—N4—C11 | 108.79 (14) |
C8—C9—H9A | 109.1 | C10—N4—H4A | 125.6 |
C10—C9—H9B | 109.1 | C11—N4—H4A | 125.6 |
C8—C9—H9B | 109.1 | H1A—O1—H1B | 105.9 |
H9A—C9—H9B | 107.8 | H2B—O2—H2C | 107.8 |
N4—C10—N3 | 109.43 (15) | H3B—O3—H3C | 101.2 |
N4—C10—C9 | 126.25 (17) | H4B—O4—H4C | 95.8 |
N1—C1—C2—C3 | 179.91 (17) | C14—C15—C16—C11 | 1.7 (3) |
C6—C1—C2—C3 | 0.4 (2) | N4—C11—C16—N3 | −0.14 (17) |
C1—C2—C3—C4 | 0.5 (3) | C12—C11—C16—N3 | 178.47 (15) |
C2—C3—C4—C5 | −1.0 (3) | N4—C11—C16—C15 | 179.97 (15) |
C3—C4—C5—C6 | 0.4 (3) | C12—C11—C16—C15 | −1.4 (3) |
C4—C5—C6—N2 | 179.99 (17) | N2—C7—N1—C1 | 0.24 (19) |
C4—C5—C6—C1 | 0.6 (3) | C8—C7—N1—C1 | −179.21 (17) |
N1—C1—C6—N2 | −0.16 (18) | C2—C1—N1—C7 | −179.59 (18) |
C2—C1—C6—N2 | 179.45 (15) | C6—C1—N1—C7 | −0.04 (18) |
N1—C1—C6—C5 | 179.38 (15) | N1—C7—N2—C6 | −0.4 (2) |
C2—C1—C6—C5 | −1.0 (3) | C8—C7—N2—C6 | 179.10 (17) |
N1—C7—C8—C9 | −117.7 (2) | C5—C6—N2—C7 | −179.16 (19) |
N2—C7—C8—C9 | 62.9 (3) | C1—C6—N2—C7 | 0.31 (19) |
C7—C8—C9—C10 | 176.41 (17) | N4—C10—N3—C16 | 1.00 (19) |
C8—C9—C10—N4 | 90.8 (2) | C9—C10—N3—C16 | −178.32 (16) |
C8—C9—C10—N3 | −90.0 (2) | C15—C16—N3—C10 | 179.36 (18) |
N4—C11—C12—C13 | 178.22 (17) | C11—C16—N3—C10 | −0.51 (18) |
C16—C11—C12—C13 | 0.0 (2) | N3—C10—N4—C11 | −1.08 (19) |
C11—C12—C13—C14 | 1.1 (3) | C9—C10—N4—C11 | 178.22 (16) |
C12—C13—C14—C15 | −0.8 (3) | C12—C11—N4—C10 | −177.67 (17) |
C13—C14—C15—C16 | −0.6 (3) | C16—C11—N4—C10 | 0.74 (18) |
C14—C15—C16—N3 | −178.17 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 1.86 | 2.719 (2) | 178 |
N2—H2A···Cl1ii | 0.86 | 2.41 | 3.201 (2) | 152 |
N3—H3A···Cl2 | 0.86 | 2.26 | 3.104 (3) | 165 |
N4—H4A···O1 | 0.86 | 1.87 | 2.711 (3) | 167 |
O1—H1A···O3 | 0.92 | 1.90 | 2.798 (3) | 166 |
O1—H1B···Cl2iii | 0.95 | 2.34 | 3.216 (2) | 152 |
O2—H2B···O4iv | 0.89 | 1.93 | 2.790 (3) | 164 |
O2—H2C···Cl1 | 0.95 | 2.31 | 3.208 (2) | 156 |
O3—H3B···Cl1 | 0.99 | 2.26 | 3.249 (3) | 174 |
O3—H3C···Cl1iv | 0.90 | 2.41 | 3.310 (3) | 176 |
O4—H4B···Cl2v | 0.95 | 2.35 | 3.300 (3) | 174 |
O4—H4C···Cl2vi | 0.90 | 2.50 | 3.383 (3) | 169 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+2, −z+1; (vi) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C16H16N42+·2Cl−·4H2O |
Mr | 407.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.174 (6), 9.652 (8), 15.411 (13) |
α, β, γ (°) | 80.504 (8), 79.684 (9), 68.520 (8) |
V (Å3) | 971.2 (14) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.17 × 0.14 × 0.08 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick,1997) |
Tmin, Tmax | 0.941, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6584, 3317, 2933 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.105, 1.09 |
No. of reflections | 3317 |
No. of parameters | 237 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.27 |
Computer programs: APEX2 (Bruker, Year?), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 1.86 | 2.719 (2) | 178.4 |
N2—H2A···Cl1ii | 0.86 | 2.41 | 3.201 (2) | 152.4 |
N3—H3A···Cl2 | 0.86 | 2.26 | 3.104 (3) | 165.3 |
N4—H4A···O1 | 0.86 | 1.87 | 2.711 (3) | 166.5 |
O1—H1A···O3 | 0.92 | 1.90 | 2.798 (3) | 166.1 |
O1—H1B···Cl2iii | 0.95 | 2.34 | 3.216 (2) | 151.7 |
O2—H2B···O4iv | 0.89 | 1.93 | 2.790 (3) | 164.4 |
O2—H2C···Cl1 | 0.95 | 2.31 | 3.208 (2) | 156.3 |
O3—H3B···Cl1 | 0.99 | 2.26 | 3.249 (3) | 174.1 |
O3—H3C···Cl1iv | 0.90 | 2.41 | 3.310 (3) | 175.7 |
O4—H4B···Cl2v | 0.95 | 2.35 | 3.300 (3) | 173.6 |
O4—H4C···Cl2vi | 0.90 | 2.50 | 3.383 (3) | 169.4 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+2, −z+1; (vi) x, y, z−1. |
We present an 'axle' type polyaromatic compound (I) that contains 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).
The molecular structure of (I), shown in Fig. 1, consists of an organic cation, Cl- anions and lattice water molecules. The two benzimidazolyl rings in the organic cation are not co-planar, with a dihedral angle of 27.77 (6)° between them. Molecules are linked via a network of hydrogen bonds (N1—H1···O2, O2—H2C···Cl1, N2—H2A···Cl1, N3—H3A···Cl2, O1—H1B···Cl2, N4—H4A···O1, O1—H1A···O3, O3—H3B···Cl1; Table 1).
π···π stacking interactions are observed between nearly parallel benzimidazolyl benzene rings. The centroid-to-centroid distance between C1–C6 benzene rings is 3.635 (3) Å (symmetry code: –X,-Y,1-Z), while between C11–C16 benzene rings it is 3.817 (3) Å (symmetry codes:1-X,1-Y,-Z). In addition, an N—H···π interaction occurs between adjacent benzimidazolyl groups, with an N1—H1···Cg(3) angle of 79.89°, and H1···Cg(3) and N1···Cg(3) distances of 3.3964Å and 3.354 (3) Å, respectively [Cg(3) is the centroid of the C1–C6-benzene (symmetry codes:1-X,-Y,1-Z)].