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organic compounds
2-[3-(1H-Benzimidazol-2-yl)propyl]-1H-benzimidazol-3-ium 3,5-dicarboxybenzoate–benzene-1,3,5-tricarboxylic acid–water (1/1/1)
aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, People's Republic of China
*Correspondence e-mail: fengguodong00805@163.com
The title compound, C17H17N4+·C9H5O6−·C9H6O6·H2O, contains a protonated 2,2′-(1,3-propanediyl)bis(1H-benzimidazole) cation, a deprotonated benzene-1,3,5-tricarboxylic acid anion, a neutral benzene-1,3,5-tricarboxylic acid molecule and a water molecule, which are linked together through N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonds into almost double sheets parallel to (4). These hydrogen-bonded sheets are packed in the crystal with the formation of centrosymmetric voids of 25.5 Å3, which are filled by the water molecules.
Related literature
For the coordination chemistry of bis-benzimidazoles, see: Sun et al. (2010). For the clinical applications of the benzimidazole ring system, see Harrell et al. (2004
). For novel proton-transfer compounds, see Aghabozorg et al. (2008
). For applications of benzimidazole and bis-benzimidazole compounds, see: Chang et al. (2008
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2005); cell SAINT (Bruker, 2005
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL-Plus (Sheldrick, 2008
); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536810039139/pb2041sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039139/pb2041Isup2.hkl
The compound was prepared by a hydrothermal method. A mixture of 2,2'-(1,3-propanediyl)bis(1H-benzimidazole)(0.5 mmol), benzene-1,3,5-tricarboxylic acid (0.6 mmol),and water (10 ml) was stirred for 20 min and then transferred to a 23 ml Teflon reactor. The reactor was kept at 433 K for 72 h under autogenous pressure. Single crystals were obtained after cooling to room temperature.
All H atoms were placed in calculated positions and refined in a riding-model approximation with; C—H = 0.95–0.99 Å, N—H = 0.88 Å, O—H = 0.83–0.85Å and Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(O).
Bis-benzimidazoles are known to be strong chelating agents coordinating through both of the C=N group nitrogen atoms (Sun et al., 2010). Recently, The benzimidazole ring system is present in clinically approved anthelmintics, antiulcers, antivirals, and antihistamines (Harrell, et al., 2004).
A number of cases were reported in which a proton transferred from a carboxylic acid to an amine to form some novel proton transfer compounds (Aghabozorg et al., 2008). In this work, we report a new proton transfer compound obtained from benzene-1,3,5-tricarboxylic acid as a proton donor and bis-benzimidazoles as an acceptor.
The
of the title proton transfer compound shows that a single proton from one of the carboxyl groups of the benzene-1,3,5-tricarboxylic acids was transferred to the N-ring atom of benzimidazoles. On the other hand, an interesting feature exhibited by the is that just one benzene-1,3,5-tricarboxylic acids as a proton donor and another benzene-1,3,5-tricarboxylic acids is in an un-ionized state. The two benzene-1,3,5-tricarboxylic acids are parallel. In the intermolecular N—H···O,O—H···O and weak C—H···O hydrogen bonds (Table 1) link cations and anions into double-planar parallel to the (4,-4,-1) plane. These hydrogen-bonded sheets are further packed into crystal with the formation of centrosymmetric voids of 25.5 Å3, which are filled by the disordered water molecules.For literature on the coordination chemistry of bis-benzimidazoles, see: Sun et al. (2010). For literature on the clinical applications of the benzimidazole ring system, see Harrell et al. (2004). For literature on novel proton transfer compounds, see Aghabozorg et al. (2008). For related literature [on ?], see: Chang et al. (2008).
Data collection: SMART (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C17H17N4+·C9H5O6−·C9H6O6·H2O | Z = 2 |
Mr = 714.63 | F(000) = 744 |
Triclinic, P1 | Dx = 1.468 Mg m−3 |
a = 8.7711 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8389 (6) Å | Cell parameters from 165 reflections |
c = 17.2999 (9) Å | θ = 2.8–23.6° |
α = 81.520 (5)° | µ = 0.11 mm−1 |
β = 84.131 (4)° | T = 293 K |
γ = 86.998 (4)° | Block, colorless |
V = 1617.02 (13) Å3 | 0.4 × 0.32 × 0.2 mm |
Bruker APEX CCD area-detector diffractometer | 5657 independent reflections |
Radiation source: fine-focus sealed tube | 3630 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.957, Tmax = 0.977 | k = −12→12 |
9922 measured reflections | l = −20→20 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0349P)2] where P = (Fo2 + 2Fc2)/3 |
5657 reflections | (Δ/σ)max < 0.001 |
469 parameters | Δρmax = 0.28 e Å−3 |
3 restraints | Δρmin = −0.22 e Å−3 |
C17H17N4+·C9H5O6−·C9H6O6·H2O | γ = 86.998 (4)° |
Mr = 714.63 | V = 1617.02 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.7711 (3) Å | Mo Kα radiation |
b = 10.8389 (6) Å | µ = 0.11 mm−1 |
c = 17.2999 (9) Å | T = 293 K |
α = 81.520 (5)° | 0.4 × 0.32 × 0.2 mm |
β = 84.131 (4)° |
Bruker APEX CCD area-detector diffractometer | 5657 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3630 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.977 | Rint = 0.023 |
9922 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 3 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.28 e Å−3 |
5657 reflections | Δρmin = −0.22 e Å−3 |
469 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 | 0.9366 (2) | 0.70532 (19) | 0.12984 (12) | 0.0472 (5) | |
H221 | 0.8725 | 0.6395 | 0.1302 | 0.057* | |
C2 | 0.9969 (2) | 0.7728 (2) | 0.06116 (13) | 0.0597 (6) | |
H222 | 0.9733 | 0.7522 | 0.0136 | 0.072* | |
C3 | 1.0926 (2) | 0.8712 (2) | 0.06101 (13) | 0.0651 (7) | |
H223 | 1.1301 | 0.9150 | 0.0131 | 0.078* | |
C4 | 1.1335 (2) | 0.9060 (2) | 0.12862 (13) | 0.0542 (6) | |
H224 | 1.1979 | 0.9716 | 0.1281 | 0.065* | |
C5 | 1.07310 (18) | 0.83745 (17) | 0.19804 (11) | 0.0372 (5) | |
C6 | 0.97641 (18) | 0.74056 (16) | 0.19828 (11) | 0.0341 (4) | |
C7 | 0.99913 (18) | 0.76278 (17) | 0.32189 (11) | 0.0355 (4) | |
C8 | 0.9711 (2) | 0.74754 (18) | 0.40866 (11) | 0.0433 (5) | |
H8A | 1.0687 | 0.7459 | 0.4307 | 0.052* | |
H8B | 0.9248 | 0.6679 | 0.4271 | 0.052* | |
C9 | 0.8672 (2) | 0.85092 (18) | 0.43867 (11) | 0.0428 (5) | |
H9A | 0.9056 | 0.9307 | 0.4135 | 0.051* | |
H9B | 0.8744 | 0.8465 | 0.4946 | 0.051* | |
C10 | 0.6983 (2) | 0.8473 (2) | 0.42501 (10) | 0.0458 (5) | |
H10A | 0.6598 | 0.7672 | 0.4496 | 0.055* | |
H10B | 0.6412 | 0.9114 | 0.4508 | 0.055* | |
C11 | 0.66781 (17) | 0.86607 (16) | 0.34136 (10) | 0.0325 (4) | |
C12 | 0.57954 (18) | 0.83069 (16) | 0.23153 (10) | 0.0332 (4) | |
C13 | 0.5143 (2) | 0.7843 (2) | 0.17270 (12) | 0.0523 (6) | |
H13 | 0.4556 | 0.7137 | 0.1832 | 0.063* | |
C14 | 0.5407 (2) | 0.8473 (2) | 0.09827 (13) | 0.0579 (6) | |
H14 | 0.4997 | 0.8184 | 0.0571 | 0.069* | |
C15 | 0.6273 (2) | 0.9538 (2) | 0.08258 (11) | 0.0501 (5) | |
H15 | 0.6404 | 0.9955 | 0.0315 | 0.060* | |
C16 | 0.69382 (19) | 0.99856 (17) | 0.14092 (10) | 0.0376 (5) | |
H16 | 0.7530 | 1.0689 | 0.1302 | 0.045* | |
C17 | 0.66929 (17) | 0.93482 (15) | 0.21629 (10) | 0.0278 (4) | |
C18 | 0.46437 (16) | 0.20168 (15) | 0.29690 (9) | 0.0248 (4) | |
C19 | 0.49709 (17) | 0.24146 (15) | 0.21723 (9) | 0.0283 (4) | |
H19 | 0.4573 | 0.2003 | 0.1807 | 0.034* | |
C20 | 0.58961 (18) | 0.34311 (16) | 0.19206 (9) | 0.0295 (4) | |
C21 | 0.64414 (18) | 0.40664 (16) | 0.24701 (9) | 0.0303 (4) | |
H21 | 0.7039 | 0.4756 | 0.2300 | 0.036* | |
C22 | 0.61089 (17) | 0.36895 (15) | 0.32672 (9) | 0.0260 (4) | |
C23 | 0.52217 (17) | 0.26558 (15) | 0.35086 (9) | 0.0273 (4) | |
H23 | 0.5009 | 0.2384 | 0.4042 | 0.033* | |
C24 | 0.37076 (18) | 0.08932 (16) | 0.32472 (10) | 0.0288 (4) | |
C25 | 0.6362 (2) | 0.38696 (18) | 0.10842 (10) | 0.0380 (5) | |
C26 | 0.67101 (18) | 0.43956 (16) | 0.38498 (10) | 0.0298 (4) | |
C27 | 0.18279 (17) | 0.44108 (16) | 0.18951 (9) | 0.0294 (4) | |
C28 | 0.08562 (18) | 0.34199 (16) | 0.21251 (10) | 0.0315 (4) | |
H28 | 0.0461 | 0.3032 | 0.1748 | 0.038* | |
C29 | 0.04780 (17) | 0.30111 (15) | 0.29153 (9) | 0.0278 (4) | |
C30 | 0.10540 (17) | 0.36020 (15) | 0.34742 (9) | 0.0282 (4) | |
H30 | 0.0790 | 0.3333 | 0.4004 | 0.034* | |
C31 | 0.20262 (17) | 0.45961 (15) | 0.32504 (9) | 0.0248 (4) | |
C32 | 0.23957 (17) | 0.49858 (15) | 0.24616 (10) | 0.0294 (4) | |
H32 | 0.3041 | 0.5650 | 0.2307 | 0.035* | |
C33 | 0.2313 (2) | 0.48724 (17) | 0.10617 (10) | 0.0380 (5) | |
C34 | −0.05308 (18) | 0.19177 (16) | 0.31858 (10) | 0.0325 (4) | |
C35 | 0.27119 (17) | 0.52423 (16) | 0.38307 (10) | 0.0287 (4) | |
N1 | 0.93470 (15) | 0.69651 (13) | 0.27654 (8) | 0.0348 (4) | |
H1A | 0.8758 | 0.6353 | 0.2931 | 0.042* | |
N2 | 1.08535 (15) | 0.84712 (14) | 0.27610 (9) | 0.0402 (4) | |
H2A | 1.1402 | 0.8996 | 0.2925 | 0.048* | |
N3 | 0.72286 (14) | 0.95552 (13) | 0.28622 (8) | 0.0305 (3) | |
N4 | 0.57988 (15) | 0.79119 (14) | 0.31099 (9) | 0.0375 (4) | |
H4A | 0.5316 | 0.7288 | 0.3369 | 0.045* | |
O1 | 0.16654 (16) | 0.43594 (14) | 0.05506 (7) | 0.0646 (5) | |
H1 | 0.1992 | 0.4662 | 0.0106 | 0.097* | |
O2 | 0.32635 (14) | 0.56827 (13) | 0.08772 (7) | 0.0491 (4) | |
O3 | 0.34628 (14) | 0.61690 (12) | 0.36169 (7) | 0.0446 (3) | |
O4 | 0.24293 (14) | 0.47490 (11) | 0.45530 (7) | 0.0460 (4) | |
H4 | 0.2837 | 0.5149 | 0.4837 | 0.069* | |
O5 | −0.08461 (16) | 0.15746 (13) | 0.38823 (7) | 0.0574 (4) | |
O6 | −0.09809 (13) | 0.14016 (12) | 0.26303 (7) | 0.0464 (4) | |
H6 | −0.1521 | 0.0816 | 0.2819 | 0.070* | |
O7 | 0.37661 (14) | 0.05198 (12) | 0.40002 (7) | 0.0461 (4) | |
H7 | 0.3245 | −0.0096 | 0.4136 | 0.069* | |
O8 | 0.30023 (13) | 0.03803 (12) | 0.28260 (7) | 0.0425 (3) | |
O9 | 0.57854 (15) | 0.32907 (13) | 0.05788 (7) | 0.0555 (4) | |
H9 | 0.6104 | 0.3591 | 0.0132 | 0.083* | |
O10 | 0.72506 (17) | 0.47175 (14) | 0.08869 (7) | 0.0657 (5) | |
O11 | 0.74251 (14) | 0.53540 (12) | 0.36033 (7) | 0.0474 (4) | |
O12 | 0.64331 (14) | 0.39760 (11) | 0.45685 (7) | 0.0428 (3) | |
O1W | 0.27197 (15) | 0.84782 (13) | 0.47477 (8) | 0.0601 (4) | |
H2 | 0.2094 | 0.8558 | 0.5152 | 0.090* | |
H3 | 0.3126 | 0.7750 | 0.4838 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0492 (11) | 0.0476 (13) | 0.0471 (13) | −0.0132 (10) | 0.0003 (10) | −0.0137 (11) |
C2 | 0.0618 (13) | 0.0745 (17) | 0.0432 (13) | −0.0145 (12) | 0.0032 (11) | −0.0119 (12) |
C3 | 0.0638 (14) | 0.0800 (19) | 0.0451 (14) | −0.0162 (13) | 0.0106 (12) | 0.0061 (13) |
C4 | 0.0456 (12) | 0.0538 (15) | 0.0588 (15) | −0.0215 (10) | 0.0096 (11) | 0.0035 (12) |
C5 | 0.0306 (9) | 0.0390 (12) | 0.0417 (12) | −0.0072 (8) | −0.0007 (8) | −0.0050 (9) |
C6 | 0.0307 (9) | 0.0310 (11) | 0.0399 (11) | −0.0049 (8) | 0.0011 (8) | −0.0046 (9) |
C7 | 0.0315 (9) | 0.0315 (11) | 0.0436 (12) | −0.0020 (8) | −0.0067 (9) | −0.0036 (9) |
C8 | 0.0480 (11) | 0.0414 (12) | 0.0416 (12) | −0.0058 (9) | −0.0133 (9) | −0.0020 (10) |
C9 | 0.0619 (12) | 0.0398 (12) | 0.0281 (10) | −0.0050 (9) | −0.0125 (9) | −0.0035 (9) |
C10 | 0.0516 (12) | 0.0543 (14) | 0.0297 (11) | −0.0072 (10) | 0.0017 (9) | −0.0022 (10) |
C11 | 0.0299 (9) | 0.0319 (11) | 0.0340 (10) | −0.0047 (8) | 0.0019 (8) | −0.0018 (9) |
C12 | 0.0310 (9) | 0.0316 (11) | 0.0363 (11) | −0.0096 (8) | −0.0026 (8) | −0.0001 (9) |
C13 | 0.0524 (12) | 0.0532 (14) | 0.0553 (14) | −0.0302 (10) | −0.0108 (11) | −0.0065 (12) |
C14 | 0.0576 (13) | 0.0755 (17) | 0.0466 (14) | −0.0257 (12) | −0.0172 (11) | −0.0122 (12) |
C15 | 0.0509 (11) | 0.0655 (15) | 0.0343 (11) | −0.0164 (11) | −0.0110 (10) | 0.0019 (11) |
C16 | 0.0383 (10) | 0.0351 (11) | 0.0385 (11) | −0.0128 (8) | −0.0038 (9) | 0.0022 (9) |
C17 | 0.0280 (9) | 0.0264 (10) | 0.0296 (10) | −0.0052 (7) | −0.0048 (8) | −0.0030 (8) |
C18 | 0.0283 (9) | 0.0249 (10) | 0.0211 (9) | −0.0041 (7) | −0.0012 (7) | −0.0029 (7) |
C19 | 0.0336 (9) | 0.0290 (10) | 0.0243 (10) | −0.0061 (7) | −0.0041 (7) | −0.0080 (8) |
C20 | 0.0372 (9) | 0.0306 (10) | 0.0208 (9) | −0.0097 (8) | −0.0005 (8) | −0.0026 (8) |
C21 | 0.0360 (9) | 0.0295 (10) | 0.0251 (10) | −0.0127 (8) | −0.0005 (8) | −0.0007 (8) |
C22 | 0.0310 (9) | 0.0263 (10) | 0.0213 (9) | −0.0068 (7) | −0.0019 (7) | −0.0033 (8) |
C23 | 0.0334 (9) | 0.0280 (10) | 0.0203 (9) | −0.0058 (7) | −0.0021 (7) | −0.0017 (8) |
C24 | 0.0326 (9) | 0.0288 (10) | 0.0251 (10) | −0.0064 (8) | 0.0020 (8) | −0.0058 (8) |
C25 | 0.0524 (11) | 0.0419 (12) | 0.0214 (10) | −0.0198 (9) | −0.0023 (9) | −0.0046 (9) |
C26 | 0.0371 (9) | 0.0282 (11) | 0.0249 (10) | −0.0097 (8) | −0.0030 (8) | −0.0036 (8) |
C27 | 0.0352 (9) | 0.0312 (11) | 0.0215 (9) | −0.0090 (8) | −0.0015 (8) | −0.0009 (8) |
C28 | 0.0362 (9) | 0.0338 (11) | 0.0262 (10) | −0.0100 (8) | −0.0049 (8) | −0.0061 (8) |
C29 | 0.0314 (9) | 0.0278 (10) | 0.0240 (9) | −0.0078 (7) | −0.0036 (7) | −0.0005 (8) |
C30 | 0.0335 (9) | 0.0283 (10) | 0.0219 (9) | −0.0067 (7) | −0.0011 (7) | 0.0003 (8) |
C31 | 0.0289 (8) | 0.0228 (10) | 0.0229 (9) | −0.0049 (7) | −0.0030 (7) | −0.0026 (7) |
C32 | 0.0348 (9) | 0.0261 (10) | 0.0267 (10) | −0.0121 (8) | −0.0005 (8) | 0.0008 (8) |
C33 | 0.0493 (11) | 0.0399 (12) | 0.0260 (10) | −0.0186 (9) | 0.0004 (9) | −0.0050 (9) |
C34 | 0.0348 (10) | 0.0315 (11) | 0.0327 (12) | −0.0121 (8) | −0.0051 (8) | −0.0041 (9) |
C35 | 0.0325 (9) | 0.0283 (10) | 0.0252 (10) | −0.0069 (8) | −0.0006 (8) | −0.0029 (8) |
N1 | 0.0359 (8) | 0.0276 (9) | 0.0409 (10) | −0.0117 (7) | −0.0010 (7) | −0.0031 (7) |
N2 | 0.0348 (8) | 0.0367 (10) | 0.0515 (11) | −0.0159 (7) | −0.0061 (7) | −0.0071 (8) |
N3 | 0.0339 (8) | 0.0300 (9) | 0.0275 (8) | −0.0087 (6) | −0.0005 (6) | −0.0022 (7) |
N4 | 0.0376 (8) | 0.0312 (9) | 0.0417 (10) | −0.0166 (7) | 0.0004 (7) | 0.0035 (7) |
O1 | 0.0948 (11) | 0.0814 (11) | 0.0217 (7) | −0.0564 (9) | −0.0007 (7) | −0.0055 (7) |
O2 | 0.0662 (8) | 0.0569 (9) | 0.0247 (7) | −0.0361 (7) | 0.0015 (6) | 0.0000 (6) |
O3 | 0.0600 (8) | 0.0431 (8) | 0.0326 (7) | −0.0306 (7) | −0.0048 (6) | −0.0016 (6) |
O4 | 0.0741 (9) | 0.0448 (9) | 0.0225 (7) | −0.0326 (7) | −0.0075 (6) | −0.0034 (6) |
O5 | 0.0845 (10) | 0.0606 (10) | 0.0279 (8) | −0.0454 (8) | 0.0000 (7) | 0.0023 (7) |
O6 | 0.0582 (8) | 0.0465 (9) | 0.0372 (8) | −0.0322 (7) | −0.0033 (6) | −0.0048 (7) |
O7 | 0.0704 (9) | 0.0426 (8) | 0.0260 (7) | −0.0324 (7) | −0.0022 (6) | 0.0016 (6) |
O8 | 0.0525 (7) | 0.0419 (8) | 0.0363 (7) | −0.0251 (6) | −0.0087 (6) | −0.0050 (6) |
O9 | 0.0903 (10) | 0.0597 (10) | 0.0190 (7) | −0.0410 (8) | −0.0007 (7) | −0.0041 (7) |
O10 | 0.0969 (11) | 0.0798 (11) | 0.0235 (7) | −0.0626 (9) | 0.0040 (7) | −0.0039 (7) |
O11 | 0.0700 (9) | 0.0423 (8) | 0.0329 (7) | −0.0348 (7) | −0.0027 (6) | −0.0049 (6) |
O12 | 0.0710 (8) | 0.0401 (8) | 0.0200 (7) | −0.0265 (7) | −0.0052 (6) | −0.0040 (6) |
O1W | 0.0641 (8) | 0.0412 (9) | 0.0669 (10) | −0.0139 (7) | 0.0056 (7) | 0.0145 (7) |
C1—C2 | 1.372 (3) | C19—H19 | 0.9300 |
C1—C6 | 1.379 (2) | C20—C21 | 1.388 (2) |
C1—H221 | 0.9300 | C20—C25 | 1.478 (2) |
C2—C3 | 1.391 (3) | C21—C22 | 1.385 (2) |
C2—H222 | 0.9300 | C21—H21 | 0.9300 |
C3—C4 | 1.367 (3) | C22—C23 | 1.386 (2) |
C3—H223 | 0.9300 | C22—C26 | 1.503 (2) |
C4—C5 | 1.386 (3) | C23—H23 | 0.9300 |
C4—H224 | 0.9300 | C24—O8 | 1.2127 (19) |
C5—N2 | 1.385 (2) | C24—O7 | 1.311 (2) |
C5—C6 | 1.383 (2) | C25—O10 | 1.2232 (19) |
C6—N1 | 1.386 (2) | C25—O9 | 1.304 (2) |
C7—N1 | 1.323 (2) | C26—O11 | 1.2399 (19) |
C7—N2 | 1.331 (2) | C26—O12 | 1.2628 (19) |
C7—C8 | 1.482 (3) | C27—C32 | 1.382 (2) |
C8—C9 | 1.524 (2) | C27—C28 | 1.392 (2) |
C8—H8A | 0.9700 | C27—C33 | 1.481 (2) |
C8—H8B | 0.9700 | C28—C29 | 1.385 (2) |
C9—C10 | 1.528 (2) | C28—H28 | 0.9300 |
C9—H9A | 0.9700 | C29—C30 | 1.384 (2) |
C9—H9B | 0.9700 | C29—C34 | 1.506 (2) |
C10—C11 | 1.481 (2) | C30—C31 | 1.394 (2) |
C10—H10A | 0.9700 | C30—H30 | 0.9300 |
C10—H10B | 0.9700 | C31—C32 | 1.378 (2) |
C11—N3 | 1.329 (2) | C31—C35 | 1.495 (2) |
C11—N4 | 1.343 (2) | C32—H32 | 0.9300 |
C12—N4 | 1.378 (2) | C33—O2 | 1.2277 (19) |
C12—C13 | 1.384 (2) | C33—O1 | 1.302 (2) |
C12—C17 | 1.388 (2) | C34—O5 | 1.215 (2) |
C13—C14 | 1.369 (3) | C34—O6 | 1.2853 (19) |
C13—H13 | 0.9300 | C35—O3 | 1.2204 (18) |
C14—C15 | 1.393 (3) | C35—O4 | 1.2893 (19) |
C14—H14 | 0.9300 | N1—H1A | 0.8600 |
C15—C16 | 1.374 (2) | N2—H2A | 0.8600 |
C15—H15 | 0.9300 | N4—H4A | 0.8600 |
C16—C17 | 1.384 (2) | O1—H1 | 0.8200 |
C16—H16 | 0.9300 | O4—H4 | 0.8200 |
C17—N3 | 1.394 (2) | O6—H6 | 0.8200 |
C18—C19 | 1.387 (2) | O7—H7 | 0.8200 |
C18—C23 | 1.390 (2) | O9—H9 | 0.8200 |
C18—C24 | 1.497 (2) | O1W—H2 | 0.8561 |
C19—C20 | 1.394 (2) | O1W—H3 | 0.8490 |
C2—C1—C6 | 116.25 (18) | C20—C19—H19 | 120.0 |
C2—C1—H221 | 121.9 | C21—C20—C19 | 119.67 (15) |
C6—C1—H221 | 121.9 | C21—C20—C25 | 117.19 (14) |
C1—C2—C3 | 121.6 (2) | C19—C20—C25 | 123.13 (14) |
C1—C2—H222 | 119.2 | C22—C21—C20 | 121.04 (14) |
C3—C2—H222 | 119.2 | C22—C21—H21 | 119.5 |
C4—C3—C2 | 122.5 (2) | C20—C21—H21 | 119.5 |
C4—C3—H223 | 118.8 | C23—C22—C21 | 118.60 (15) |
C2—C3—H223 | 118.8 | C23—C22—C26 | 121.43 (15) |
C3—C4—C5 | 115.98 (18) | C21—C22—C26 | 119.98 (14) |
C3—C4—H224 | 122.0 | C22—C23—C18 | 121.36 (15) |
C5—C4—H224 | 122.0 | C22—C23—H23 | 119.3 |
C4—C5—N2 | 132.23 (17) | C18—C23—H23 | 119.3 |
C4—C5—C6 | 121.61 (18) | O8—C24—O7 | 124.20 (15) |
N2—C5—C6 | 106.13 (15) | O8—C24—C18 | 124.19 (16) |
C1—C6—N1 | 131.79 (16) | O7—C24—C18 | 111.60 (14) |
C1—C6—C5 | 122.11 (17) | O10—C25—O9 | 122.68 (15) |
N1—C6—C5 | 106.09 (15) | O10—C25—C20 | 121.29 (15) |
N1—C7—N2 | 108.36 (16) | O9—C25—C20 | 116.02 (14) |
N1—C7—C8 | 124.59 (16) | O11—C26—O12 | 123.93 (15) |
N2—C7—C8 | 126.98 (17) | O11—C26—C22 | 118.80 (15) |
C7—C8—C9 | 113.30 (16) | O12—C26—C22 | 117.27 (14) |
C7—C8—H8A | 108.9 | C32—C27—C28 | 119.36 (15) |
C9—C8—H8A | 108.9 | C32—C27—C33 | 117.75 (14) |
C7—C8—H8B | 108.9 | C28—C27—C33 | 122.88 (15) |
C9—C8—H8B | 108.9 | C29—C28—C27 | 120.05 (15) |
H8A—C8—H8B | 107.7 | C29—C28—H28 | 120.0 |
C8—C9—C10 | 115.43 (15) | C27—C28—H28 | 120.0 |
C8—C9—H9A | 108.4 | C30—C29—C28 | 119.73 (14) |
C10—C9—H9A | 108.4 | C30—C29—C34 | 118.75 (15) |
C8—C9—H9B | 108.4 | C28—C29—C34 | 121.51 (15) |
C10—C9—H9B | 108.4 | C29—C30—C31 | 120.69 (15) |
H9A—C9—H9B | 107.5 | C29—C30—H30 | 119.7 |
C11—C10—C9 | 114.59 (14) | C31—C30—H30 | 119.7 |
C11—C10—H10A | 108.6 | C32—C31—C30 | 118.75 (14) |
C9—C10—H10A | 108.6 | C32—C31—C35 | 118.50 (13) |
C11—C10—H10B | 108.6 | C30—C31—C35 | 122.74 (14) |
C9—C10—H10B | 108.6 | C27—C32—C31 | 121.41 (14) |
H10A—C10—H10B | 107.6 | C27—C32—H32 | 119.3 |
N3—C11—N4 | 110.65 (15) | C31—C32—H32 | 119.3 |
N3—C11—C10 | 126.11 (16) | O2—C33—O1 | 123.21 (16) |
N4—C11—C10 | 123.23 (15) | O2—C33—C27 | 121.45 (15) |
N4—C12—C13 | 132.57 (16) | O1—C33—C27 | 115.34 (14) |
N4—C12—C17 | 105.30 (15) | O5—C34—O6 | 124.88 (15) |
C13—C12—C17 | 122.10 (17) | O5—C34—C29 | 120.36 (15) |
C14—C13—C12 | 116.70 (17) | O6—C34—C29 | 114.75 (15) |
C14—C13—H13 | 121.6 | O3—C35—O4 | 124.28 (15) |
C12—C13—H13 | 121.6 | O3—C35—C31 | 120.99 (15) |
C13—C14—C15 | 121.71 (19) | O4—C35—C31 | 114.73 (14) |
C13—C14—H14 | 119.1 | C7—N1—C6 | 109.82 (14) |
C15—C14—H14 | 119.1 | C7—N1—H1A | 125.1 |
C16—C15—C14 | 121.43 (19) | C6—N1—H1A | 125.1 |
C16—C15—H15 | 119.3 | C7—N2—C5 | 109.58 (15) |
C14—C15—H15 | 119.3 | C7—N2—H2A | 125.2 |
C15—C16—C17 | 117.37 (16) | C5—N2—H2A | 125.2 |
C15—C16—H16 | 121.3 | C11—N3—C17 | 106.47 (13) |
C17—C16—H16 | 121.3 | C11—N4—C12 | 108.91 (13) |
C16—C17—C12 | 120.65 (15) | C11—N4—H4A | 125.5 |
C16—C17—N3 | 130.69 (14) | C12—N4—H4A | 125.5 |
C12—C17—N3 | 108.65 (14) | C33—O1—H1 | 109.5 |
C19—C18—C23 | 119.38 (14) | C35—O4—H4 | 109.5 |
C19—C18—C24 | 120.47 (14) | C34—O6—H6 | 109.5 |
C23—C18—C24 | 120.14 (15) | C24—O7—H7 | 109.5 |
C18—C19—C20 | 119.91 (15) | C25—O9—H9 | 109.5 |
C18—C19—H19 | 120.0 | H2—O1W—H3 | 105.4 |
C6—C1—C2—C3 | −0.1 (3) | C21—C20—C25—O9 | −177.31 (16) |
C1—C2—C3—C4 | 0.7 (4) | C19—C20—C25—O9 | 3.7 (3) |
C2—C3—C4—C5 | −0.3 (3) | C23—C22—C26—O11 | −176.01 (16) |
C3—C4—C5—N2 | −178.11 (19) | C21—C22—C26—O11 | 4.1 (2) |
C3—C4—C5—C6 | −0.5 (3) | C23—C22—C26—O12 | 3.1 (2) |
C2—C1—C6—N1 | 178.2 (2) | C21—C22—C26—O12 | −176.72 (17) |
C2—C1—C6—C5 | −0.7 (3) | C32—C27—C28—C29 | −0.6 (3) |
C4—C5—C6—C1 | 1.1 (3) | C33—C27—C28—C29 | 178.26 (17) |
N2—C5—C6—C1 | 179.23 (16) | C27—C28—C29—C30 | 0.8 (3) |
C4—C5—C6—N1 | −178.06 (17) | C27—C28—C29—C34 | −178.12 (15) |
N2—C5—C6—N1 | 0.1 (2) | C28—C29—C30—C31 | −0.7 (2) |
N1—C7—C8—C9 | −104.6 (2) | C34—C29—C30—C31 | 178.24 (15) |
N2—C7—C8—C9 | 72.0 (2) | C29—C30—C31—C32 | 0.4 (2) |
C7—C8—C9—C10 | 72.0 (2) | C29—C30—C31—C35 | −178.30 (15) |
C8—C9—C10—C11 | −64.1 (2) | C28—C27—C32—C31 | 0.3 (3) |
C9—C10—C11—N3 | −48.0 (3) | C33—C27—C32—C31 | −178.63 (16) |
C9—C10—C11—N4 | 131.08 (18) | C30—C31—C32—C27 | −0.2 (3) |
N4—C12—C13—C14 | −178.6 (2) | C35—C31—C32—C27 | 178.58 (15) |
C17—C12—C13—C14 | −1.0 (3) | C32—C27—C33—O2 | 4.6 (3) |
C12—C13—C14—C15 | −0.7 (3) | C28—C27—C33—O2 | −174.27 (18) |
C13—C14—C15—C16 | 1.8 (3) | C32—C27—C33—O1 | −175.43 (17) |
C14—C15—C16—C17 | −1.0 (3) | C28—C27—C33—O1 | 5.7 (3) |
C15—C16—C17—C12 | −0.6 (3) | C30—C29—C34—O5 | 1.0 (3) |
C15—C16—C17—N3 | 178.61 (17) | C28—C29—C34—O5 | 179.92 (18) |
N4—C12—C17—C16 | 179.87 (16) | C30—C29—C34—O6 | −178.12 (15) |
C13—C12—C17—C16 | 1.7 (3) | C28—C29—C34—O6 | 0.8 (2) |
N4—C12—C17—N3 | 0.49 (18) | C32—C31—C35—O3 | 6.9 (2) |
C13—C12—C17—N3 | −177.72 (16) | C30—C31—C35—O3 | −174.34 (16) |
C23—C18—C19—C20 | 1.2 (2) | C32—C31—C35—O4 | −173.69 (16) |
C24—C18—C19—C20 | −177.37 (15) | C30—C31—C35—O4 | 5.0 (2) |
C18—C19—C20—C21 | −2.2 (3) | N2—C7—N1—C6 | −1.6 (2) |
C18—C19—C20—C25 | 176.72 (17) | C8—C7—N1—C6 | 175.51 (17) |
C19—C20—C21—C22 | 1.4 (3) | C1—C6—N1—C7 | −178.09 (19) |
C25—C20—C21—C22 | −177.55 (17) | C5—C6—N1—C7 | 0.9 (2) |
C20—C21—C22—C23 | 0.3 (3) | N1—C7—N2—C5 | 1.7 (2) |
C20—C21—C22—C26 | −179.84 (15) | C8—C7—N2—C5 | −175.36 (17) |
C21—C22—C23—C18 | −1.3 (2) | C4—C5—N2—C7 | 176.8 (2) |
C26—C22—C23—C18 | 178.84 (15) | C6—C5—N2—C7 | −1.1 (2) |
C19—C18—C23—C22 | 0.5 (2) | N4—C11—N3—C17 | −1.25 (19) |
C24—C18—C23—C22 | 179.15 (15) | C10—C11—N3—C17 | 177.92 (16) |
C19—C18—C24—O8 | −11.2 (3) | C16—C17—N3—C11 | −178.86 (18) |
C23—C18—C24—O8 | 170.21 (16) | C12—C17—N3—C11 | 0.44 (18) |
C19—C18—C24—O7 | 167.73 (15) | N3—C11—N4—C12 | 1.6 (2) |
C23—C18—C24—O7 | −10.9 (2) | C10—C11—N4—C12 | −177.60 (16) |
C21—C20—C25—O10 | 3.5 (3) | C13—C12—N4—C11 | 176.7 (2) |
C19—C20—C25—O10 | −175.51 (18) | C17—C12—N4—C11 | −1.24 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O10i | 0.82 | 1.82 | 2.6404 (16) | 178 |
O9—H9···O2i | 0.82 | 1.85 | 2.6682 (16) | 177 |
N1—H1A···O11 | 0.86 | 1.84 | 2.6560 (17) | 159 |
N4—H4A···O3 | 0.86 | 2.05 | 2.8435 (17) | 153 |
C1—H221···O10 | 0.93 | 2.51 | 3.414 (2) | 163 |
C9—H9A···O5ii | 0.97 | 2.44 | 3.346 (2) | 156 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H17N4+·C9H5O6−·C9H6O6·H2O |
Mr | 714.63 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.7711 (3), 10.8389 (6), 17.2999 (9) |
α, β, γ (°) | 81.520 (5), 84.131 (4), 86.998 (4) |
V (Å3) | 1617.02 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.4 × 0.32 × 0.2 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.957, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9922, 5657, 3630 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.081, 1.07 |
No. of reflections | 5657 |
No. of parameters | 469 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.22 |
Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O10i | 0.82 | 1.82 | 2.6404 (16) | 178.0 |
O9—H9···O2i | 0.82 | 1.85 | 2.6682 (16) | 177.2 |
N1—H1A···O11 | 0.86 | 1.84 | 2.6560 (17) | 158.6 |
N4—H4A···O3 | 0.86 | 2.05 | 2.8435 (17) | 152.8 |
C1—H221···O10 | 0.93 | 2.51 | 3.414 (2) | 163.0 |
C9—H9A···O5ii | 0.97 | 2.44 | 3.346 (2) | 156.0 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y+1, z. |
Acknowledgements
This work was supported financially by the Foundation for Young Teachers of Baoji University of Arts and Science (grant No. ZK09135).
References
Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
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Chang, C. M., Kulkarni, M. V., Chen, C. H., Wang, C. & Sun, C. M. (2008). J. Comb. Chem. 10, 466–474. Web of Science CrossRef PubMed CAS Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Bis-benzimidazoles are known to be strong chelating agents coordinating through both of the C=N group nitrogen atoms (Sun et al., 2010). Recently, The benzimidazole ring system is present in clinically approved anthelmintics, antiulcers, antivirals, and antihistamines (Harrell, et al., 2004).
A number of cases were reported in which a proton transferred from a carboxylic acid to an amine to form some novel proton transfer compounds (Aghabozorg et al., 2008). In this work, we report a new proton transfer compound obtained from benzene-1,3,5-tricarboxylic acid as a proton donor and bis-benzimidazoles as an acceptor.
The crystal structure of the title proton transfer compound shows that a single proton from one of the carboxyl groups of the benzene-1,3,5-tricarboxylic acids was transferred to the N-ring atom of benzimidazoles. On the other hand, an interesting feature exhibited by the crystal structure is that just one benzene-1,3,5-tricarboxylic acids as a proton donor and another benzene-1,3,5-tricarboxylic acids is in an un-ionized state. The two benzene-1,3,5-tricarboxylic acids are parallel. In the crystal structure, intermolecular N—H···O,O—H···O and weak C—H···O hydrogen bonds (Table 1) link cations and anions into double-planar parallel to the (4,-4,-1) plane. These hydrogen-bonded sheets are further packed into crystal with the formation of centrosymmetric voids of 25.5 Å3, which are filled by the disordered water molecules.