organic compounds
Adipic acid–2,6-bis(1H-benzimidazol-2-yl)pyridine–water (1/2/4)
aNortheast Dianli University, Jilin 132012, People's Republic of China
*Correspondence e-mail: songzhulin@hotmail.com
The 19H13N5·C6H10O4·4H2O, consists of one 2,6-bis(1H-benzimidazol-2-yl)pyridine molecule, half of an adipic acid molecule (bisected by an inversion center) and two water solvates. In the crystal, N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds and π–π interactions [centroid–centroid distances = 3.769 (2) and 3.731 (2) Å] form a three-dimensional supramolecular structure.
of the title hydrated 2CRelated literature
For related structures, see: Boča et al. (2000); Chetia & Iyer (2006, 2007); Xiao et al. (2010); Freire et al. (2003); Lin et al. (2012).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
10.1107/S1600536812047861/bg2486sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047861/bg2486Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047861/bg2486Isup3.cml
The title compound was obtained by 2,6-bis(benzimidazol-2-yl)pyridine (0.062 g, 0.20 mmol) and adipic acid (0.029 g, 0.20 mmol) dissolved in 30 ml solution mixed with ethanol and water by 2:1(V/V) was heated to refluxed for 8 h and cooled to the room temperature. Single crystals suitable for X-ray measurements were obtained by recrystallization at room temperature.
The positions of all H atoms were found in a difference Fourier map, and refined both in coordinates as in displacement factors. Those attached to O were subject to distance restraints (O-H = 0.85 (1)Å).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
2C19H13N5·C6H10O4·4H2O | Z = 1 |
Mr = 840.90 | F(000) = 442 |
Triclinic, P1 | Dx = 1.345 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0709 (18) Å | Cell parameters from 25 reflections |
b = 9.6882 (19) Å | θ = 4–14° |
c = 12.311 (3) Å | µ = 0.10 mm−1 |
α = 88.93 (3)° | T = 295 K |
β = 83.12 (3)° | Block, yellow |
γ = 75.14 (3)° | 0.25 × 0.18 × 0.16 mm |
V = 1038.1 (4) Å3 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 3.0° |
Graphite monochromator | h = −11→11 |
ω scans | k = −12→12 |
10214 measured reflections | l = −15→15 |
4705 independent reflections | 3 standard reflections every 100 reflections |
3555 reflections with I > 2σ(I) | intensity decay: none |
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) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.0268P] where P = (Fo2 + 2Fc2)/3 |
4705 reflections | (Δ/σ)max < 0.001 |
368 parameters | Δρmax = 0.36 e Å−3 |
7 restraints | Δρmin = −0.19 e Å−3 |
2C19H13N5·C6H10O4·4H2O | γ = 75.14 (3)° |
Mr = 840.90 | V = 1038.1 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.0709 (18) Å | Mo Kα radiation |
b = 9.6882 (19) Å | µ = 0.10 mm−1 |
c = 12.311 (3) Å | T = 295 K |
α = 88.93 (3)° | 0.25 × 0.18 × 0.16 mm |
β = 83.12 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.024 |
10214 measured reflections | 3 standard reflections every 100 reflections |
4705 independent reflections | intensity decay: none |
3555 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.047 | 7 restraints |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.36 e Å−3 |
4705 reflections | Δρmin = −0.19 e Å−3 |
368 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
N1 | 0.13159 (14) | 0.33800 (13) | −0.15941 (10) | 0.0488 (3) | |
N2 | 0.11534 (14) | 0.56273 (13) | −0.10937 (10) | 0.0469 (3) | |
H4 | 0.142 (2) | 0.632 (2) | −0.0672 (17) | 0.070 (5)* | |
N3 | 0.30720 (13) | 0.47411 (12) | 0.04908 (9) | 0.0425 (3) | |
N4 | 0.35862 (15) | 0.69020 (12) | 0.16663 (10) | 0.0461 (3) | |
H5 | 0.296 (2) | 0.718 (2) | 0.1169 (17) | 0.071 (6)* | |
N5 | 0.51881 (14) | 0.53946 (12) | 0.26517 (10) | 0.0467 (3) | |
C1 | 0.03749 (17) | 0.43165 (17) | −0.22421 (12) | 0.0502 (3) | |
C2 | −0.0392 (2) | 0.4018 (2) | −0.30889 (15) | 0.0660 (5) | |
H2B | −0.029 (3) | 0.302 (3) | −0.331 (2) | 0.108 (9)* | |
C3 | −0.1263 (2) | 0.5167 (3) | −0.36062 (17) | 0.0737 (5) | |
H3B | −0.177 (2) | 0.500 (2) | −0.4221 (17) | 0.075 (6)* | |
C4 | −0.1367 (2) | 0.6559 (3) | −0.32926 (17) | 0.0738 (6) | |
H4B | −0.203 (2) | 0.737 (2) | −0.3704 (18) | 0.083 (6)* | |
C5 | −0.0618 (2) | 0.6887 (2) | −0.24504 (16) | 0.0625 (4) | |
H5B | −0.071 (2) | 0.784 (2) | −0.2255 (17) | 0.072 (6)* | |
C6 | 0.02658 (16) | 0.57252 (17) | −0.19362 (12) | 0.0495 (4) | |
C7 | 0.17580 (15) | 0.42054 (14) | −0.09313 (11) | 0.0436 (3) | |
C8 | 0.28186 (15) | 0.37145 (14) | −0.01174 (11) | 0.0423 (3) | |
C9 | 0.35464 (18) | 0.22746 (15) | −0.00130 (13) | 0.0500 (4) | |
H9A | 0.3296 (19) | 0.1624 (19) | −0.0465 (15) | 0.053 (4)* | |
C10 | 0.45920 (19) | 0.18978 (15) | 0.07321 (13) | 0.0533 (4) | |
H10A | 0.517 (2) | 0.086 (2) | 0.0801 (15) | 0.064 (5)* | |
C11 | 0.48672 (19) | 0.29346 (15) | 0.13676 (13) | 0.0496 (4) | |
H11A | 0.553 (2) | 0.2771 (19) | 0.1892 (15) | 0.058 (5)* | |
C12 | 0.40660 (15) | 0.43502 (14) | 0.12290 (11) | 0.0423 (3) | |
C13 | 0.42912 (15) | 0.55179 (14) | 0.18674 (11) | 0.0424 (3) | |
C14 | 0.50736 (17) | 0.67897 (15) | 0.29760 (12) | 0.0461 (3) | |
C15 | 0.5824 (2) | 0.72962 (19) | 0.37449 (15) | 0.0590 (4) | |
H15A | 0.653 (3) | 0.659 (2) | 0.4172 (19) | 0.085 (6)* | |
C16 | 0.5557 (2) | 0.8759 (2) | 0.38559 (16) | 0.0678 (5) | |
H16A | 0.607 (2) | 0.915 (2) | 0.4359 (18) | 0.080 (6)* | |
C17 | 0.4553 (2) | 0.96933 (19) | 0.32354 (16) | 0.0686 (5) | |
H17A | 0.442 (2) | 1.074 (2) | 0.3320 (17) | 0.080 (6)* | |
C18 | 0.3784 (2) | 0.92146 (17) | 0.24903 (14) | 0.0588 (4) | |
H18A | 0.308 (2) | 0.984 (2) | 0.2049 (17) | 0.072 (6)* | |
C19 | 0.40766 (17) | 0.77399 (15) | 0.23620 (12) | 0.0465 (3) | |
O1 | 0.67965 (16) | 0.37143 (12) | 0.40769 (11) | 0.0688 (4) | |
H1 | 0.630 (2) | 0.411 (2) | 0.3538 (14) | 0.084 (7)* | |
O2 | 0.74254 (17) | 0.17221 (13) | 0.30895 (11) | 0.0732 (4) | |
C20 | 0.75243 (17) | 0.23700 (16) | 0.38907 (13) | 0.0491 (3) | |
C21 | 0.8489 (2) | 0.17588 (17) | 0.47764 (14) | 0.0538 (4) | |
H21A | 0.784 (3) | 0.179 (2) | 0.5432 (19) | 0.079 (6)* | |
H21B | 0.915 (2) | 0.250 (2) | 0.4912 (16) | 0.073 (6)* | |
C22 | 0.9496 (2) | 0.02613 (17) | 0.45481 (14) | 0.0543 (4) | |
H22A | 0.883 (2) | −0.040 (2) | 0.4464 (16) | 0.069 (5)* | |
H22B | 1.019 (2) | 0.022 (2) | 0.3830 (17) | 0.071 (5)* | |
O1W | 0.14244 (18) | 0.04491 (14) | 0.85092 (11) | 0.0742 (4) | |
O2W | 0.14234 (16) | 0.82851 (14) | 0.01294 (13) | 0.0751 (4) | |
H1WA | 0.153 (3) | 0.1282 (13) | 0.8350 (18) | 0.102 (8)* | |
H1WB | 0.172 (3) | −0.0080 (19) | 0.7943 (13) | 0.093 (8)* | |
H2WB | 0.064 (3) | 0.870 (3) | 0.058 (2) | 0.152 (13)* | |
H2WA | 0.151 (3) | 0.896 (2) | −0.0326 (18) | 0.126 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0533 (7) | 0.0439 (7) | 0.0461 (7) | −0.0062 (5) | −0.0072 (5) | −0.0025 (5) |
N2 | 0.0474 (6) | 0.0400 (6) | 0.0505 (7) | −0.0060 (5) | −0.0065 (5) | 0.0026 (5) |
N3 | 0.0460 (6) | 0.0359 (5) | 0.0420 (6) | −0.0054 (5) | −0.0027 (5) | 0.0022 (4) |
N4 | 0.0533 (7) | 0.0361 (6) | 0.0453 (7) | −0.0042 (5) | −0.0081 (5) | 0.0051 (5) |
N5 | 0.0524 (7) | 0.0387 (6) | 0.0450 (6) | −0.0034 (5) | −0.0080 (5) | −0.0001 (5) |
C1 | 0.0489 (8) | 0.0545 (8) | 0.0434 (8) | −0.0071 (7) | −0.0036 (6) | −0.0008 (6) |
C2 | 0.0642 (10) | 0.0800 (13) | 0.0525 (10) | −0.0130 (9) | −0.0134 (8) | −0.0017 (9) |
C3 | 0.0645 (11) | 0.0970 (15) | 0.0574 (11) | −0.0116 (10) | −0.0188 (9) | 0.0053 (10) |
C4 | 0.0572 (10) | 0.0880 (14) | 0.0688 (12) | −0.0038 (10) | −0.0142 (9) | 0.0243 (11) |
C5 | 0.0539 (9) | 0.0595 (10) | 0.0681 (11) | −0.0048 (8) | −0.0074 (8) | 0.0158 (8) |
C6 | 0.0429 (7) | 0.0524 (8) | 0.0491 (8) | −0.0068 (6) | −0.0025 (6) | 0.0079 (6) |
C7 | 0.0452 (7) | 0.0374 (7) | 0.0438 (7) | −0.0047 (6) | −0.0005 (6) | 0.0003 (5) |
C8 | 0.0449 (7) | 0.0379 (7) | 0.0403 (7) | −0.0060 (6) | −0.0005 (5) | 0.0001 (5) |
C9 | 0.0589 (8) | 0.0353 (7) | 0.0522 (8) | −0.0058 (6) | −0.0058 (7) | −0.0029 (6) |
C10 | 0.0638 (9) | 0.0345 (7) | 0.0552 (9) | −0.0002 (7) | −0.0097 (7) | 0.0018 (6) |
C11 | 0.0568 (8) | 0.0379 (7) | 0.0498 (8) | −0.0027 (6) | −0.0110 (7) | 0.0047 (6) |
C12 | 0.0461 (7) | 0.0363 (6) | 0.0410 (7) | −0.0056 (6) | −0.0025 (5) | 0.0021 (5) |
C13 | 0.0451 (7) | 0.0354 (6) | 0.0424 (7) | −0.0034 (5) | −0.0038 (5) | 0.0042 (5) |
C14 | 0.0520 (8) | 0.0401 (7) | 0.0423 (7) | −0.0064 (6) | −0.0018 (6) | −0.0031 (6) |
C15 | 0.0625 (9) | 0.0558 (9) | 0.0554 (9) | −0.0064 (8) | −0.0111 (7) | −0.0087 (7) |
C16 | 0.0759 (11) | 0.0624 (10) | 0.0662 (11) | −0.0187 (9) | −0.0073 (9) | −0.0187 (9) |
C17 | 0.0898 (13) | 0.0429 (8) | 0.0714 (12) | −0.0168 (9) | −0.0015 (10) | −0.0101 (8) |
C18 | 0.0761 (11) | 0.0375 (7) | 0.0587 (10) | −0.0090 (7) | −0.0035 (8) | 0.0002 (7) |
C19 | 0.0543 (8) | 0.0387 (7) | 0.0430 (7) | −0.0078 (6) | −0.0006 (6) | 0.0009 (6) |
O1 | 0.0873 (9) | 0.0462 (6) | 0.0612 (7) | 0.0133 (6) | −0.0288 (7) | −0.0021 (5) |
O2 | 0.0936 (9) | 0.0482 (6) | 0.0773 (8) | 0.0008 (6) | −0.0494 (7) | −0.0055 (6) |
C20 | 0.0528 (8) | 0.0410 (7) | 0.0520 (8) | −0.0055 (6) | −0.0152 (6) | 0.0062 (6) |
C21 | 0.0598 (9) | 0.0492 (8) | 0.0475 (9) | −0.0009 (7) | −0.0154 (7) | 0.0048 (6) |
C22 | 0.0600 (9) | 0.0463 (8) | 0.0543 (9) | −0.0033 (7) | −0.0209 (8) | 0.0062 (7) |
O1W | 0.1059 (10) | 0.0511 (7) | 0.0632 (8) | −0.0195 (7) | −0.0014 (7) | −0.0007 (6) |
O2W | 0.0710 (8) | 0.0589 (7) | 0.0809 (10) | 0.0058 (6) | −0.0037 (7) | 0.0200 (7) |
N1—C7 | 1.3166 (19) | C11—C12 | 1.3957 (19) |
N1—C1 | 1.388 (2) | C11—H11A | 0.917 (19) |
N2—C7 | 1.3664 (17) | C12—C13 | 1.459 (2) |
N2—C6 | 1.375 (2) | C14—C15 | 1.394 (2) |
N2—H4 | 0.95 (2) | C14—C19 | 1.395 (2) |
N3—C8 | 1.3375 (18) | C15—C16 | 1.381 (3) |
N3—C12 | 1.3381 (19) | C15—H15A | 1.00 (2) |
N4—C13 | 1.3617 (17) | C16—C17 | 1.397 (3) |
N4—C19 | 1.376 (2) | C16—H16A | 0.96 (2) |
N4—H5 | 0.88 (2) | C17—C18 | 1.370 (3) |
N5—C13 | 1.3201 (18) | C17—H17A | 1.00 (2) |
N5—C14 | 1.3911 (18) | C18—C19 | 1.393 (2) |
C1—C2 | 1.394 (2) | C18—H18A | 0.98 (2) |
C1—C6 | 1.398 (2) | O1—C20 | 1.3109 (19) |
C2—C3 | 1.383 (3) | O1—H1 | 0.873 (10) |
C2—H2B | 0.99 (3) | O2—C20 | 1.203 (2) |
C3—C4 | 1.386 (3) | C20—C21 | 1.498 (2) |
C3—H3B | 0.97 (2) | C21—C22 | 1.514 (2) |
C4—C5 | 1.388 (3) | C21—H21A | 0.94 (2) |
C4—H4B | 1.03 (2) | C21—H21B | 1.07 (2) |
C5—C6 | 1.394 (2) | C22—C22i | 1.522 (3) |
C5—H5B | 0.94 (2) | C22—H22A | 1.001 (19) |
C7—C8 | 1.461 (2) | C22—H22B | 1.02 (2) |
C8—C9 | 1.3927 (19) | O1W—H1WA | 0.854 (10) |
C9—C10 | 1.376 (2) | O1W—H1WB | 0.848 (9) |
C9—H9A | 0.935 (18) | O2W—H2WB | 0.860 (10) |
C10—C11 | 1.374 (2) | O2W—H2WA | 0.865 (10) |
C10—H10A | 1.012 (18) | ||
C7—N1—C1 | 104.88 (12) | N3—C12—C11 | 122.93 (14) |
C7—N2—C6 | 106.77 (13) | N3—C12—C13 | 115.23 (12) |
C7—N2—H4 | 120.0 (12) | C11—C12—C13 | 121.82 (14) |
C6—N2—H4 | 133.2 (12) | N5—C13—N4 | 112.69 (13) |
C8—N3—C12 | 117.85 (12) | N5—C13—C12 | 126.24 (12) |
C13—N4—C19 | 107.10 (13) | N4—C13—C12 | 121.05 (13) |
C13—N4—H5 | 125.1 (13) | N5—C14—C15 | 129.82 (15) |
C19—N4—H5 | 127.8 (13) | N5—C14—C19 | 109.63 (13) |
C13—N5—C14 | 105.00 (12) | C15—C14—C19 | 120.50 (15) |
N1—C1—C2 | 129.23 (17) | C16—C15—C14 | 117.41 (17) |
N1—C1—C6 | 109.80 (14) | C16—C15—H15A | 124.0 (13) |
C2—C1—C6 | 120.96 (16) | C14—C15—H15A | 118.6 (13) |
C3—C2—C1 | 117.3 (2) | C15—C16—C17 | 121.28 (17) |
C3—C2—H2B | 122.5 (16) | C15—C16—H16A | 120.3 (13) |
C1—C2—H2B | 120.2 (16) | C17—C16—H16A | 118.4 (13) |
C2—C3—C4 | 121.2 (2) | C18—C17—C16 | 122.09 (16) |
C2—C3—H3B | 119.3 (13) | C18—C17—H17A | 119.2 (12) |
C4—C3—H3B | 119.5 (13) | C16—C17—H17A | 118.7 (12) |
C3—C4—C5 | 122.70 (18) | C17—C18—C19 | 116.66 (17) |
C3—C4—H4B | 117.8 (13) | C17—C18—H18A | 123.8 (12) |
C5—C4—H4B | 119.5 (13) | C19—C18—H18A | 119.6 (12) |
C4—C5—C6 | 115.93 (19) | N4—C19—C18 | 132.36 (15) |
C4—C5—H5B | 121.0 (13) | N4—C19—C14 | 105.57 (12) |
C6—C5—H5B | 123.1 (13) | C18—C19—C14 | 122.03 (15) |
N2—C6—C5 | 132.52 (16) | C20—O1—H1 | 113.3 (16) |
N2—C6—C1 | 105.55 (13) | O2—C20—O1 | 123.00 (14) |
C5—C6—C1 | 121.93 (17) | O2—C20—C21 | 124.71 (14) |
N1—C7—N2 | 112.99 (13) | O1—C20—C21 | 112.28 (14) |
N1—C7—C8 | 125.67 (12) | C20—C21—C22 | 114.80 (14) |
N2—C7—C8 | 121.32 (13) | C20—C21—H21A | 108.3 (13) |
N3—C8—C9 | 122.74 (14) | C22—C21—H21A | 110.4 (13) |
N3—C8—C7 | 115.52 (12) | C20—C21—H21B | 106.6 (10) |
C9—C8—C7 | 121.71 (13) | C22—C21—H21B | 111.9 (11) |
C10—C9—C8 | 118.51 (14) | H21A—C21—H21B | 104.2 (17) |
C10—C9—H9A | 124.2 (11) | C21—C22—C22i | 111.97 (18) |
C8—C9—H9A | 117.3 (11) | C21—C22—H22A | 109.3 (11) |
C11—C10—C9 | 119.71 (13) | C22i—C22—H22A | 109.8 (11) |
C11—C10—H10A | 120.1 (10) | C21—C22—H22B | 110.5 (11) |
C9—C10—H10A | 120.2 (10) | C22i—C22—H22B | 108.1 (11) |
C10—C11—C12 | 118.22 (14) | H22A—C22—H22B | 107.0 (15) |
C10—C11—H11A | 125.1 (11) | H1WA—O1W—H1WB | 108.7 (18) |
C12—C11—H11A | 116.6 (11) | H2WB—O2W—H2WA | 102.4 (18) |
Symmetry code: (i) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H4···O2W | 0.95 (2) | 2.16 (2) | 3.084 (2) | 163.3 (18) |
N4—H5···O2W | 0.88 (2) | 2.08 (2) | 2.945 (2) | 167.6 (18) |
O1—H1···N5 | 0.87 (1) | 1.83 (1) | 2.6731 (19) | 163 (2) |
O1W—H1WA···N1ii | 0.85 (1) | 1.99 (1) | 2.8169 (18) | 162 (2) |
O1W—H1WB···O2iii | 0.85 (1) | 1.99 (1) | 2.815 (2) | 165 (2) |
O2W—H2WB···O1Wiv | 0.86 (1) | 2.05 (1) | 2.898 (2) | 170 (3) |
O2W—H2WA···O1Wv | 0.87 (1) | 2.01 (1) | 2.867 (2) | 171 (3) |
Symmetry codes: (ii) x, y, z+1; (iii) −x+1, −y, −z+1; (iv) −x, −y+1, −z+1; (v) x, y+1, z−1. |
Experimental details
Crystal data | |
Chemical formula | 2C19H13N5·C6H10O4·4H2O |
Mr | 840.90 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 9.0709 (18), 9.6882 (19), 12.311 (3) |
α, β, γ (°) | 88.93 (3), 83.12 (3), 75.14 (3) |
V (Å3) | 1038.1 (4) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.25 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10214, 4705, 3555 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.163, 1.15 |
No. of reflections | 4705 |
No. of parameters | 368 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.19 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H4···O2W | 0.95 (2) | 2.16 (2) | 3.084 (2) | 163.3 (18) |
N4—H5···O2W | 0.88 (2) | 2.08 (2) | 2.945 (2) | 167.6 (18) |
O1—H1···N5 | 0.873 (10) | 1.825 (12) | 2.6731 (19) | 163 (2) |
O1W—H1WA···N1i | 0.854 (10) | 1.993 (11) | 2.8169 (18) | 162 (2) |
O1W—H1WB···O2ii | 0.848 (9) | 1.989 (11) | 2.815 (2) | 165 (2) |
O2W—H2WB···O1Wiii | 0.860 (10) | 2.046 (12) | 2.898 (2) | 170 (3) |
O2W—H2WA···O1Wiv | 0.865 (10) | 2.009 (11) | 2.867 (2) | 171 (3) |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x, y+1, z−1. |
Acknowledgements
The authors would like to thank the National Natural Science Foundation of China (51003010), the Natural Science Foundation of Jilin Province (201115178) and the Science and Technology Development Project of Jilin Province (SKLSSM201132).
References
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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.
Structures containing 2,6-bis(benzimidazol-2-yl)pyridine have been reported in recent year (Xiao et al., 2010; Freire et al., 2003; Lin et al., 2012). As a continuation of our previous works devoted to structures with 2,6-bis(benzimidazol-2-yl)pyridine, here we report the crystal structures of the title compound (C19H13N5)0.5(C6H10O4)2(H2O)(I). Its asymmetric unit consists of one 2-pyridin-4-yl-1H-benzoimidazole molecule, half of an adipic acid molecule (bisected by an inversion center) and two water solvates. The aromatic C—C and C—N distances in both the benzimidazole and pyridine rings are within the usual range. All C and N atoms of the 2,6-bis(benzimidazol-2-yl)pyridine molecule lay in a plane (largest deviation: 0.084 Å for C16). The compound is similar to other related compounds consisting of 2,6-bis(benzimidazol-2-yl)pyridine and organic molecules (Boča et al., 2000; Chetia and Iyer, 2006; Chetia and Iyer, 2007; Xiao et al., 2010; Lin et al., 2012).
The crystal structure in (I) is a 3D array, definend by N—H···O, O—H···O, O—H···N inter- and intramolecular interactions (Table 1) and π–π stacking interactions between rings with center-to-center distances Cg1···Cg2 = 3.769 (2) (symmetry code 1 - x, 1 - y, -z), Cg2···Cg3=3.731 (2) Å (symmetry code -x, 1 - y, -z), where Cg1, Cg2 and Cg3 refer to imidazole ring N4—C13—N5—C14—C19, pyridine ring N3—C8—C9—C10—C11—C12 and phenyl ring C1—C2—C3—C4—C5—C6, respectively.